Chemical context   {#sec1}
==================

Di­thio­carbamate anions of general formula ^−^S~2~CN*RR*′, *R*/*R*′ = H, alkyl and aryl, are readily prepared from the facile reaction of an amine with CS~2~ in the presence of base. Thus, the number of derivatives which can be prepared is largely dictated by the availability of amines and hence, an enormous range of di­thio­carbamate anions are available for complexation to metals/heavy elements. A key inter­est in developing metal/heavy element compounds of di­thio­carbamates relates to their biological potential (Hogarth, 2012[@bb9]). In the context of anti-cancer properties, a number of recent reports have described the efficacy of phosphanegold (Jamaludin *et al.*, 2013[@bb12]), zinc (Tan *et al.*, 2015[@bb29]) and bis­muth (Ishak *et al.*, 2014[@bb11]) di­thio­carbamates, buoyed by the observation that many of these species promote cancer cell death by apoptosis; bis­muth derivatives exhibit *in vivo* anti-tumour activity (Li *et al.*, 2007[@bb14]). Organotin compounds are well known for their anti-cancer potential (Gielen & Tiekink, 2005[@bb7]) and there is a strong body of literature on organotin di­thio­carbamates in this context (Tiekink, 2008[@bb30]).

In the past few years, there has been a resurgence of inter­est in the anti-cancer activity of organotin di­thio­carbamates (Khan *et al.*, 2015[@bb13]; Mohamad, Awang, Kamaludin *et al.*, 2016[@bb17]) and very recently, a report on the *in vitro* cytotoxicity trial of several tin di­allyl­dithio­carbamate compounds was described as well as a preliminary assessment of anti-microbial activity (Adeyemi *et al.*, 2019[@bb2]); some phosphane-gold(I) and phosphane-silver(I) di­thio­carbamates are known to be bactericidal based on pharmacokinetic studies (Sim *et al.*, 2014[@bb25]; Tan, Tan *et al.*, 2019[@bb28]). The aforementioned report on tin di­allyl­dithio­carbamate compounds (Adeyemi *et al.*, 2019[@bb2]) also presented the first crystal-structure determinations for tin compounds of di­allyl­dithio­carbamate. In a continuation of recent structural studies in this area (Mohamad *et al.*, 2017[@bb18], 2018*a* [@bb19],*b* [@bb20]; Haezam *et al.*, 2019[@bb8]), herein, two organotin compounds of di­allyl­dithio­carbamate, (C~6~H~5~)~3~Sn\[S~2~CN(CH~2~C(H)=CH~2~)~2~\], (I)[](#scheme1){ref-type="chem"}, and (C~6~H~5~)~2~Sn\[S~2~CN(CH~2~C(H)=CH~2~)~2~\]~2~, (II)[](#scheme1){ref-type="chem"}, have been synth­esized and studied by X-ray crystallography. In addition, the supra­molecular associations in their crystals have been evaluated by Hirshfeld surface analyses and computational chemistry.

Structural commentary   {#sec2}
=======================

The tin atom in (I)[](#scheme1){ref-type="chem"}, Fig. 1[▸](#fig1){ref-type="fig"}, is coordinated by three *ipso*-carbon atoms of the phenyl groups as well as by an asymmetrically bound di­thio­carbamate anion, Table 1[▸](#table1){ref-type="table"}. There is a relatively large disparity in the Sn---S separations, *i.e*. Δ(Sn---S) = \[(Sn---S~long~) - (Sn---S~short~)\] = 0.47 Å, indicating that the Sn---S2 inter­action is weak. Evidence in support of this conclusion is seen in the pattern of C---S bond lengths. Thus, the C1---S2 bond involving the less tightly bound S2 atom is about 0.07 Å shorter than the analogous bond with the tightly bound S1 atom. Nevertheless, there is a clear influence exerted by the S2 atom upon the Sn---C bond lengths with the Sn---C31 bond being appreciably longer than the other Sn---C bonds. This is traced to the *trans* effect exerted by the S2 atom as this forms a S2---Sn---C31 angle 156.01 (5)°. It is noted that there is no other (approximate) *trans* angle subtended at the tin atom in (I)[](#scheme1){ref-type="chem"}. Assuming a five-coordinate, C~3~S~2~, geometry, the range of angles subtended at the tin atom is 65.470 (14)°, for the S1---Sn---S2 chelate angle, to the aforementioned *trans* angle. The value of τ is a convenient descriptor for the assignment of a five-coordinate geometry, which ranges in value from 0.0 for an ideal square pyramid to 1.0 for an ideal trigonal bipyramid (Addison *et al.*, 1984[@bb1]). The value of τ the case of (I)[](#scheme1){ref-type="chem"} is 0.45, which is indicative of an inter­mediate geometry with a slight tendency towards square pyramidal. On the other hand, should the coordination geometry be considered C~3~S tetra­hedral, *i.e*. the weak Sn---S2 bond was ignored, the range of tetra­hedral angles would be 91.01 (5)°, for S1---Sn---C31, to 128.76 (5)°, for S1---Sn---C11. Finally, it is noted the C1---N1 bond length of 1.330 (3) Å is consistent with significant double-bond character in this bond, which arises from a major contribution of the ^2−^S~2~C=N^+^(CH~2~C(H)=CH~2~)~2~ canonical form to the electronic structure of the di­thio­carbamate ligand.

A distinct coordination geometry for the tin atoms is noted for (II)[](#scheme1){ref-type="chem"}, Fig. 2[▸](#fig2){ref-type="fig"}, for which two independent mol­ecules comprise the crystallographic asymmetric unit. The tin atom in each mol­ecule is coordinated by two *ipso*-carbon atoms of the phenyl groups as well as by two asymmetrically bound di­thio­carbamate anions, Table 2[▸](#table2){ref-type="table"}. There is a disparity in the Sn---S separations, *i.e*. Δ(Sn---S) = 0.19 and 0.11 Å, for the S1- and S3-di­thio­carbamate anions of the first independent mol­ecule; the comparable values for the second mol­ecule are similar at 0.21 and 0.11 Å. The disparities in Δ(Sn---S) are reflected in the associated C---S bond distances, Table 2[▸](#table2){ref-type="table"}. Gratifyingly, the greater differences in C---S bonds, *i.e*. 0.03 and 0.04 Å for the S1-di­thio­carbamate anions of each independent mol­ecule, are correlated with the greater values in Δ(Sn---S). The C1---N1 and C8---N2 bond lengths in both mol­ecules are short for the reasons mentioned for (I)[](#scheme1){ref-type="chem"} above. The C~2~S~4~ coordination geometry is based on an octa­hedron and has a *cis*-disposition of the *ipso*-carbon atoms with the more tightly bound sulfur atoms close to being *trans*. A partial explanation of the lengthening of the Sn---S2 and Sn---S4 bonds relates to the *trans*-influence exerted by the phenyl substituents approximately opposite the S2 and S4 atoms.

A view of the superimposition of the two mol­ecules comprising the asymmetric unit in (II)[](#scheme1){ref-type="chem"} is shown in Fig. 3[▸](#fig3){ref-type="fig"} whereby the Sn1- and inverted-Sn2-mol­ecules are overlapped so that two chelate rings, *i.e*. (Sn1,S1,S2,C1) and (Sn2,S3,S4,C8), are coincident. This shows there are non-trivial conformational differences between the mol­ecules. While the dihedral angles between the two phenyl substituents are equal within experimental error in the two mol­ecules, *i.e*. 81.28 (13) and 81.63 (14)°, more telling are the angles they form with the respective, *cis*-disposed chelate rings, *i.e*. 81.06 (10) and 35.93 (10)° for the Sn1-mol­ecule and 15.35 (11) and 74.71 (6)° for the Sn2-mol­ecule. Differences are also noted in the relative orientations of the allyl substituents. Thus, for the overlapped di­thio­carbamate ligands, the N1---C5---C6---C7 torsion angle of −122.3 (3)° is an outlier with respect to the other torsion angles with the direct equivalent angle for the inverted Sn2-mol­ecule being 13.3 (4)°. While the N---C---C---C torsion angles for the second pair of di­thio­carbamate ligands are similar, Table 2[▸](#table2){ref-type="table"}, there is a misalignment of these ligands as seen in the dihedral angle formed between the chelate rings of 80.98 (5) and 76.55 (6)° for the Sn1- and Sn2-mol­ecules, respectively.

The difference in coordination modes of the di­thio­carbamate ligands and coordination geometries are related, at least in part, to the different Lewis acid strength of the tin atoms, with the Lewis acidity in the tri­phenyl­tin species being significantly less than that in the di­phenyl­tin species.

Supra­molecular features   {#sec3}
==========================

The only directional point of contact between mol­ecules based on the distance criteria in *PLATON* (Spek, 2020[@bb26]) are phenyl-C---H⋯π(phen­yl) inter­actions, Table 3[▸](#table3){ref-type="table"}. Here, the (C21--C26) ring is pivotal by donating a C---H atom to a symmetry-related (C31--C36) ring and the same time accepting a phenyl-C---H⋯π(phen­yl) inter­action from a (C11--C16) ring to construct a linear, supra­molecular chain aligned along the *a*-axis direction, Fig. 4[▸](#fig4){ref-type="fig"}(*a*). The chains assemble in the crystal without directional inter­actions between them, Fig. 4[▸](#fig4){ref-type="fig"}(*b*).

The mol­ecular packing in (II)[](#scheme1){ref-type="chem"} is also largely devoid of directional inter­actions. Indeed, the only connections evident are vinyl­idene-C---H⋯π(phen­yl) inter­actions, Table 4[▸](#table4){ref-type="table"}, which serve to link the independent mol­ecules comprising the asymmetric unit into a supra­molecular chain aligned along the *a-*axis direction. In essence, the vinyl­idene-hydrogen atoms of the Sn1-mol­ecule bridge translationally related Sn2-mol­ecules into a linear chain, Fig. 5[▸](#fig5){ref-type="fig"}(*a*). The chains pack without directional inter­actions between them, Fig. 5[▸](#fig5){ref-type="fig"}(*b*).

Hirshfeld surface analysis   {#sec4}
============================

In order to gain further insight into the mol­ecular packing of each of (I)[](#scheme1){ref-type="chem"} and (II)[](#scheme1){ref-type="chem"}, Hirshfeld surface calculations were performed with *Crystal Explorer 17* (Turner *et al.*, 2017[@bb31]) following literature protocols (Tan, Jotani *et al.*, 2019[@bb27]). The calculations highlight the influence of the discussed C---H⋯π inter­actions (Tables 3[▸](#table3){ref-type="table"} and 4[▸](#table4){ref-type="table"}) as well the short inter­atomic contacts collated in Table 5[▸](#table5){ref-type="table"}. The short inter­atomic contacts are indicated as diminutive or faint-red spots near the participating atoms on the Hirshfeld surfaces mapped over *d* ~norm~ for (I)[](#scheme1){ref-type="chem"} and (II)[](#scheme1){ref-type="chem"} in Figs. 6[▸](#fig6){ref-type="fig"} and 7[▸](#fig7){ref-type="fig"}, respectively. Further, the donors and acceptors of the inter­molecular C---H⋯π contacts for both (I)[](#scheme1){ref-type="chem"} and (II)[](#scheme1){ref-type="chem"} are evident as the blue bumps and red concave regions, respectively, on the Hirshfeld surfaces mapped with shape-index property shown in Fig. 8[▸](#fig8){ref-type="fig"}. In the absence of potential hydrogen bonds in (I)[](#scheme1){ref-type="chem"} and (II)[](#scheme1){ref-type="chem"}, both the blue and red regions corresponding to positive and negative electrostatic potential, respectively, on Hirshfeld surfaces mapped over electrostatic potential in Fig. 9[▸](#fig9){ref-type="fig"} and arise owing to the polarization of charges towards the participating residues.

The overall two-dimensional fingerprint plots for (I)[](#scheme1){ref-type="chem"} and the individual mol­ecules of (II)[](#scheme1){ref-type="chem"} are illustrated in Fig. 10[▸](#fig10){ref-type="fig"}(*a*), and those delineated into H⋯H, C⋯H/H⋯C and S⋯H/H⋯S contacts are illustrated in Fig. 10[▸](#fig10){ref-type="fig"}(*b*)--(*d*), respectively. The percentage contributions from different atom--atom contacts to the Hirshfeld surfaces of (I)[](#scheme1){ref-type="chem"}, Sn1- and Sn2-mol­ecules of (II)[](#scheme1){ref-type="chem"} are qu­anti­tatively summarized in Table 6[▸](#table6){ref-type="table"}. In the fingerprint plot delineated into H⋯H contacts for (I)[](#scheme1){ref-type="chem"}, Fig. 10[▸](#fig10){ref-type="fig"}(*b*), a pair of small and proximate peaks at *d* ~e~ + *d* ~i~ ∼2.2 Å results from the presence of a short inter­atomic contact between the phenyl-H15 and H24 atoms, Table 5[▸](#table5){ref-type="table"}. The presence of a single peak at *d* ~e~ + *d* ~i~ ∼2.2 Å in the analogous plot for the Sn1-mol­ecule of (II)[](#scheme1){ref-type="chem"} is due to the short H⋯H contact between the phenyl-H17 and H26 atoms. Another short inter­atomic H⋯H contact involving the H17 and H18*A* atoms of the Sn1-mol­ecule and the H9*A*2 and H13*A* atoms of the Sn2-mol­ecule, Table 5[▸](#table5){ref-type="table"}, are evident as the pair of peaks at *d* ~e~ + *d* ~i~ ∼2.2 Å and at *d* ~e~ + *d* ~i~ ∼2.3 Å in the corresponding delineated plot for the Sn2-mol­ecule.

The presence of short inter­atomic C⋯H/H⋯C contacts in each of (I)[](#scheme1){ref-type="chem"} and (II)[](#scheme1){ref-type="chem"}, summarized in Table 5[▸](#table5){ref-type="table"}, are evident as the forceps-like tips at *d* ~e~ + *d* ~i~ ∼2.8 Å in Fig. 10[▸](#fig10){ref-type="fig"}(*a*). Also, the inter­molecular C---H⋯π contacts are characterized as a pair of wings in their respective delineated plots shown in Fig. 10[▸](#fig10){ref-type="fig"}(*c*). The short inter­atomic C⋯H/H⋯C contacts in the crystal of (II)[](#scheme1){ref-type="chem"} appear as a pair of forceps-like tips at *d* ~e~ + *d* ~i~ ∼2.7 Å for the Sn1-mol­ecule and as two pairs of similar adjoining tips at the same distances *d* ~e~ + *d* ~i~ ∼2.8 Å for the Sn2-mol­ecule in the plots of Fig. 10[▸](#fig10){ref-type="fig"}(*c*). For (I)[](#scheme1){ref-type="chem"}, in the fingerprint plot delineated into S⋯H/H⋯S contacts of Fig. 10[▸](#fig10){ref-type="fig"}(*d*), the short inter­atomic contacts involving thio­carbamate-S1 and the H2*A* and H7*B* atoms are evident as the pair of conical tips at *d* ~e~ + *d* ~i~ ∼2.9 Å. Similar contacts in the crystal of (II)[](#scheme1){ref-type="chem"} are also evident as the conical tips at *d* ~e~ + *d* ~i~ ∼2.9 Å in Fig. 10[▸](#fig10){ref-type="fig"}(*d*) in the upper and lower regions of the plots for the Sn1- and Sn2-mol­ecules, respectively.

Computational chemistry   {#sec5}
=========================

The pairwise inter­action energies between the mol­ecules within the crystals of (I)[](#scheme1){ref-type="chem"} and (II)[](#scheme1){ref-type="chem"} were calculated by summing up four energy components, namely the electrostatic (*E* ~ele~), polarization (*E* ~pol~), dispersion (*E* ~dis~) and exchange-repulsion (*E* ~rep~) energies, in accord with literature protocols (Turner *et al.*, 2017[@bb31]). In the present analysis, these energies were obtained by using the wave function calculated at the HF/3-21G level of theory. The specific contacts and associated energies are qu­anti­tatively summarized in Table 7[▸](#table7){ref-type="table"}. An analysis of these energies for (I)[](#scheme1){ref-type="chem"} and (II)[](#scheme1){ref-type="chem"} reveals that the dispersive component makes the major contribution to all the specified inter­molecular inter­actions in the crystals of (I)[](#scheme1){ref-type="chem"} and (II)[](#scheme1){ref-type="chem"}. However, as clearly evident from the relevant inter­action energies listed in Table 7[▸](#table7){ref-type="table"} and in the Hirshfeld surfaces mapped over the electrostatic potential of Fig. 9[▸](#fig9){ref-type="fig"}, where intense blue and red regions are apparent around the donors and acceptors, the C---H⋯π contacts in (II)[](#scheme1){ref-type="chem"} have more significant contributions from the *E* ~ele~ component, in contrast to mainly dispersive contributions in the case of (I)[](#scheme1){ref-type="chem"}.

A further noticeable observation about the strength of the inter­molecular inter­actions from Table 7[▸](#table7){ref-type="table"} is that those inter­molecular contacts arising from the same pair of symmetry-related mol­ecules have the greater inter­action energies. The magnitudes of inter­molecular energies were also represented graphically by energy frameworks to view the supra­molecular architecture of both the crystals through cylinders joining the centroids of mol­ecular pairs using red, green and blue colour codes for the *E* ~ele~, *E* ~disp~ and *E* ~tot~ terms, respectively. In summary, the images of Fig. 11[▸](#fig11){ref-type="fig"} highlight the importance of dispersion forces in the crystals of (I)[](#scheme1){ref-type="chem"} and (II)[](#scheme1){ref-type="chem"}.

Database survey   {#sec6}
=================

As a result of having several important applications, such as biological activity as alluded to in the *Chemical Context*, a relatively large number of organotin di­thio­carbamates have been synthesized and investigated by X-ray crystallography (Tiekink, 2008[@bb30]). The coordination geometry described for (I)[](#scheme1){ref-type="chem"} conforms with literature expectations in that all *R* ~3~Sn(S~2~CN*R*′*R*′′) mol­ecules conform to this structural motif (Tiekink, 2008[@bb30]; Mohamad *et al.*, 2018*a* [@bb19]). The Sn---S1 bond length in (I)[](#scheme1){ref-type="chem"} of 2.4749 (4) Å is slightly longer that the average Sn---S~short~ bond of 2.47 Å in all Ph~3~Sn(S~2~CN*R*′*R*′′) structures, while the Sn---S2 bond of 2.9456 (5) Å in (I)[](#scheme1){ref-type="chem"} is about 0.10 Å shorter than the average Sn---S~long~ of 3.04 Å in these structures. Consistent with these trends, Δ(Sn---S) in (I)[](#scheme1){ref-type="chem"} of 0.47 Å is less than the average Δ(Sn---S) value of 0.57 Å calculated from all Ph~3~Sn(S~2~CN*R*′*R*′′) structures.

Greater structural diversity is noted for *R* ~2~Sn(S~2~CN*R*′*R*′′)~2~ (Tiekink, 2008[@bb30]), including differences in coordination numbers and geometries (Mohamad, Awang, Jotani *et al.*, 2016[@bb16]). Of the now, 17 structures of the general formula Ph~2~Sn(S~2~CN*R*′*R*′′)~2~, nine adopt the *cis*-C~2~S~4~ structural motif exemplified by (II)[](#scheme1){ref-type="chem"}, including the two polymorphs of Ph~2~Sn(S~2~CNEt~2~)~2~ (Lindley & Carr, 1974[@bb15]; Hook *et al.*, 1994[@bb10]). The remaining structures adopt the usual motif for *R* ~2~Sn(S~2~CN*R*′*R*′′)~2~, namely a geometry based on a bipyramidal skewed-bipyramid. Here, the di­thio­carbamate ligands coordinate in an asymmetric fashion with the tin-bound phenyl substituents disposed to lie over the weaker Sn---S bonds, exemplified by the two independent mol­ecules comprising the asymmetric unit of Ph~2~Sn\[S~2~CN(Me)Hex\]~2~ (Hex = *n*-hexyl, --C~7~H~15~) (Ramasamy *et al.*, 2013[@bb21]). Clearly there is a subtle inter­play between the electronic and steric characteristics of the di­thio­carbamate ligands and mol­ecular packing effects in determining the structural motif adopted by Ph~2~Sn(S~2~CN*R*′*R*′′)~2~ in their respective crystals.

Synthesis and crystallization   {#sec7}
===============================

All chemicals and solvents were used as purchased without purification. The melting point was determined using an automated melting point apparatus (MPA 120 EZ-Melt). Carbon, hydrogen and nitro­gen analyses were performed on a Leco CHNS-932 Elemental Analyzer.

The synthesis of (I)[](#scheme1){ref-type="chem"} and (II)[](#scheme1){ref-type="chem"} followed established literature procedures (Awang *et al.*, 2011[@bb4]; Ajibade *et al.*, 2011[@bb3]). For each synthesis, initially, di­allyl­amine (Aldrich; 1.27 ml, 10 mmol) dissolved in ethanol (30 ml) was stirred under ice-bath conditions for 20 mins. A 25% ammonia solution (1 to 2 ml) was added followed by stirring for 30 mins to establish basic conditions. Then, a cold ethano­lic solution of carbon di­sulfide (0.60 ml, 10 mmol) was added dropwise into the solution and stirred for about 2 h.

For (I)[](#scheme1){ref-type="chem"}, tri­phenyl­tin(IV) dichloride (Merck; 3.85 g, 10 mmol) dissolved in ethanol (20--30 ml) was added dropwise into the di­allyl­dithio­carbamate solution and further stirred for 2 to 3 h. Next, the precipitate that formed was filtered off and washed with cold ethanol a few times to remove any impurities. Finally, the filtered precipitate was dried in a desiccator overnight. Recrystallization was carried out by dissolving the compound in a chloro­form and ethanol solvent mixture (5 ml; 1:1 *v*/*v*), which was allowed to slowly evaporate at room temperature yielding colourless crystals. Yield: 44%. M.p. 454.8--456.2 K. Elemental analysis: calculated (%): C 57.51, H 4.79, N 2.68. Found (%): C 56.92, H 4.93, N 2.93.

Compound (II)[](#scheme1){ref-type="chem"} was prepared and recrystallized as for (I)[](#scheme1){ref-type="chem"} but, using di­phenyl­tin(IV) dichloride (Merck; 1.72 g, 5 mmol) dissolved in ethanol (20-30 ml). Yield: 52%. M.p. 332.5--334.4 K. Elemental analysis: calculated (%): C 50.59, H 4.86, N 4.54. Found (%): C 50.20, H 4.80, N 4.20.

Refinement   {#sec8}
============

Crystal data, data collection and structure refinement details are summarized in Table 8[▸](#table8){ref-type="table"}. Carbon-bound H atoms were placed in calculated positions (C---H = 0.95--0.99 Å) and were included in the refinement in the riding-model approximation, with *U* ~iso~(H) set to 1.2*U* ~eq~(C). In (II)[](#scheme1){ref-type="chem"}, the maximum and minimum residual electron density peaks of 1.23 and 0.73 e Å^−3^, respectively, were located 0.80 and 0.74 Å from the S2 and Sn1 atoms, respectively.

Supplementary Material
======================

Crystal structure: contains datablock(s) I, II, global. DOI: [10.1107/S2056989020000122/hb7884sup1.cif](https://doi.org/10.1107/S2056989020000122/hb7884sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S2056989020000122/hb7884Isup2.hkl](https://doi.org/10.1107/S2056989020000122/hb7884Isup2.hkl)

Structure factors: contains datablock(s) II. DOI: [10.1107/S2056989020000122/hb7884IIsup3.hkl](https://doi.org/10.1107/S2056989020000122/hb7884IIsup3.hkl)

CCDC references: [1975797](https://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1975797), [1975796](https://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1975796)

Additional supporting information: [crystallographic information](https://scripts.iucr.org/cgi-bin/sendsupfiles?hb7884&file=hb7884sup0.html&mime=text/html); [3D view](https://scripts.iucr.org/cgi-bin/sendcif?hb7884sup1&Qmime=cif); [checkCIF report](https://scripts.iucr.org/cgi-bin/paper?hb7884&checkcif=yes)

The authors gratefully acknowledge the Faculty of Health Sciences and the Faculty of Science and Technology of the Universiti Kebangsaan Malaysia for providing essential laboratory facilities and for technical support from the laboratory assistants. The Universiti Teknologi MARA Puncak Alam is thanked for the elemental analysis.

(*N*,*N*-Diallyldithiocarbamato-κ^2^*S*,*S*\')\\ triphenyltin(IV) (I). Crystal data {#d1e182}
===================================================================================

  ------------------------------------- ----------------------------------------
  \[Sn(C~6~H~5~)~3~(C~7~H~10~NS~2~)\]   *F*(000) = 1056
  *M~r~* = 522.27                       *D*~x~ = 1.467 Mg m^−3^
  Monoclinic, *P*2~1~/*c*               Cu *K*α radiation, λ = 1.54184 Å
  *a* = 8.0650 (1) Å                    Cell parameters from 34049 reflections
  *b* = 11.4490 (1) Å                   θ = 3.4--76.3°
  *c* = 25.8775 (2) Å                   µ = 10.32 mm^−1^
  β = 98.282 (1)°                       *T* = 100 K
  *V* = 2364.51 (4) Å^3^                Prism, colourless
  *Z* = 4                               0.13 × 0.10 × 0.04 mm
  ------------------------------------- ----------------------------------------

(*N*,*N*-Diallyldithiocarbamato-κ^2^*S*,*S*\')\\ triphenyltin(IV) (I). Data collection {#d1e316}
======================================================================================

  ------------------------------------------------------------------------------ --------------------------------------
  XtaLAB Synergy, Dualflex, AtlasS2 diffractometer                               4226 independent reflections
  Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source   4083 reflections with *I* \> 2σ(*I*)
  Mirror monochromator                                                           *R*~int~ = 0.044
  Detector resolution: 5.2558 pixels mm^-1^                                      θ~max~ = 67.1°, θ~min~ = 3.5°
  ω scans                                                                        *h* = −9→9
  Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2018)                *k* = −13→13
  *T*~min~ = 0.807, *T*~max~ = 1.000                                             *l* = −26→30
  55086 measured reflections                                                     
  ------------------------------------------------------------------------------ --------------------------------------

(*N*,*N*-Diallyldithiocarbamato-κ^2^*S*,*S*\')\\ triphenyltin(IV) (I). Refinement {#d1e433}
=================================================================================

  ------------------------------------- ------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.020   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.053                  H-atom parameters constrained
  *S* = 1.01                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.034*P*)^2^ + 1.0941*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  4226 reflections                      (Δ/σ)~max~ = 0.001
  262 parameters                        Δρ~max~ = 0.82 e Å^−3^
  0 restraints                          Δρ~min~ = −0.50 e Å^−3^
  ------------------------------------- ------------------------------------------------------------------------------------------------

(*N*,*N*-Diallyldithiocarbamato-κ^2^*S*,*S*\')\\ triphenyltin(IV) (I). Special details {#d1e589}
======================================================================================

  -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
  -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

(*N*,*N*-Diallyldithiocarbamato-κ^2^*S*,*S*\')\\ triphenyltin(IV) (I). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#d1e608}
=========================================================================================================================================================================

  ----- ------------- --------------- -------------- -------------------- --
        *x*           *y*             *z*            *U*~iso~\*/*U*~eq~   
  Sn    0.25851 (2)   0.27508 (2)     0.37027 (2)    0.01943 (6)          
  S1    0.40753 (6)   0.34500 (4)     0.45492 (2)    0.02546 (11)         
  S2    0.50865 (6)   0.11062 (4)     0.42287 (2)    0.02585 (11)         
  N1    0.6650 (2)    0.22704 (13)    0.50510 (7)    0.0221 (3)           
  C1    0.5424 (2)    0.22413 (16)    0.46477 (8)    0.0211 (4)           
  C2    0.6883 (2)    0.32426 (18)    0.54246 (8)    0.0267 (4)           
  H2A   0.646687      0.397215        0.524565       0.032\*              
  H2B   0.809419      0.334224        0.554922       0.032\*              
  C3    0.5978 (3)    0.3042 (2)      0.58847 (8)    0.0309 (5)           
  H3    0.612847      0.360684        0.615638       0.037\*              
  C4    0.4992 (3)    0.2149 (2)      0.59435 (9)    0.0319 (5)           
  H4A   0.480682      0.156449        0.568121       0.038\*              
  H4B   0.446654      0.209057        0.624828       0.038\*              
  C5    0.7846 (2)    0.12945 (18)    0.51605 (8)    0.0249 (4)           
  H5A   0.732148      0.056406        0.501157       0.030\*              
  H5B   0.812801      0.118925        0.554284       0.030\*              
  C6    0.9410 (3)    0.1527 (2)      0.49311 (9)    0.0315 (4)           
  H6    0.931935      0.161093        0.456289       0.038\*              
  C7    1.0904 (3)    0.1621 (2)      0.52078 (11)   0.0427 (6)           
  H7A   1.103510      0.154114        0.557684       0.051\*              
  H7B   1.185305      0.176968        0.503870       0.051\*              
  C11   0.0883 (2)    0.13134 (16)    0.35523 (7)    0.0204 (4)           
  C12   −0.0823 (2)   0.15586 (18)    0.34399 (7)    0.0257 (4)           
  H12   −0.120299     0.233677        0.347295       0.031\*              
  C13   −0.1979 (2)   0.06837 (19)    0.32802 (8)    0.0278 (4)           
  H13   −0.313765     0.086573        0.320597       0.033\*              
  C14   −0.1442 (3)   −0.04484 (19)   0.32295 (8)    0.0279 (4)           
  H14   −0.222732     −0.104752       0.311737       0.033\*              
  C15   0.0259 (3)    −0.07077 (18)   0.33438 (9)    0.0308 (4)           
  H15   0.063245      −0.148801       0.331218       0.037\*              
  C16   0.1410 (2)    0.01651 (17)    0.35033 (8)    0.0254 (4)           
  H16   0.256747      −0.002093       0.357990       0.030\*              
  C21   0.4161 (2)    0.28918 (16)    0.31120 (7)    0.0213 (4)           
  C22   0.5403 (2)    0.37446 (18)    0.31258 (8)    0.0269 (4)           
  H22   0.554696      0.429581        0.340305       0.032\*              
  C23   0.6428 (3)    0.37983 (19)    0.27407 (9)    0.0312 (5)           
  H23   0.726432      0.438594        0.275407       0.037\*              
  C24   0.6234 (3)    0.2996 (2)      0.23361 (9)    0.0313 (5)           
  H24   0.693634      0.303209        0.207178       0.038\*              
  C25   0.5010 (3)    0.21372 (18)    0.23174 (8)    0.0280 (4)           
  H25   0.487954      0.158250        0.204148       0.034\*              
  C26   0.3979 (2)    0.20907 (17)    0.27018 (8)    0.0223 (4)           
  H26   0.313726      0.150577        0.268562       0.027\*              
  C31   0.0978 (2)    0.42764 (17)    0.36369 (8)    0.0242 (4)           
  C32   −0.0065 (3)   0.45310 (18)    0.40077 (8)    0.0293 (4)           
  H32   −0.007314     0.402694        0.429894       0.035\*              
  C33   −0.1095 (3)   0.5512 (2)      0.39575 (10)   0.0357 (5)           
  H33   −0.180213     0.567475        0.421210       0.043\*              
  C34   −0.1081 (3)   0.62513 (19)    0.35328 (10)   0.0374 (5)           
  H34   −0.177793     0.692406        0.349818       0.045\*              
  C35   −0.0067 (3)   0.60157 (19)    0.31626 (9)    0.0350 (5)           
  H35   −0.006485     0.652566        0.287313       0.042\*              
  C36   0.0959 (2)    0.50318 (18)    0.32102 (8)    0.0273 (4)           
  H36   0.165193      0.487164        0.295126       0.033\*              
  ----- ------------- --------------- -------------- -------------------- --

(*N*,*N*-Diallyldithiocarbamato-κ^2^*S*,*S*\')\\ triphenyltin(IV) (I). Atomic displacement parameters (Å^2^) {#d1e1334}
============================================================================================================

  ----- ------------- ------------- ------------- -------------- --------------- ---------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^         *U*^23^
  Sn    0.02063 (8)   0.01640 (8)   0.02001 (8)   0.00251 (4)    −0.00135 (5)    −0.00007 (4)
  S1    0.0271 (2)    0.0215 (2)    0.0253 (2)    0.00683 (18)   −0.00475 (18)   −0.00472 (17)
  S2    0.0301 (2)    0.0205 (2)    0.0254 (2)    0.00408 (18)   −0.00133 (18)   −0.00396 (18)
  N1    0.0206 (8)    0.0200 (9)    0.0246 (8)    0.0016 (6)     −0.0007 (7)     0.0000 (6)
  C1    0.0186 (9)    0.0212 (10)   0.0232 (9)    0.0002 (7)     0.0025 (7)      0.0024 (7)
  C2    0.0249 (10)   0.0223 (10)   0.0303 (10)   −0.0022 (8)    −0.0051 (8)     −0.0028 (8)
  C3    0.0314 (11)   0.0333 (11)   0.0255 (10)   0.0014 (9)     −0.0043 (8)     −0.0109 (9)
  C4    0.0289 (11)   0.0404 (13)   0.0257 (10)   0.0021 (9)     0.0015 (8)      −0.0050 (8)
  C5    0.0215 (9)    0.0240 (10)   0.0282 (10)   0.0029 (8)     0.0005 (7)      0.0037 (8)
  C6    0.0285 (10)   0.0312 (11)   0.0356 (11)   0.0057 (9)     0.0074 (9)      0.0036 (9)
  C7    0.0255 (11)   0.0398 (14)   0.0632 (16)   0.0002 (10)    0.0083 (10)     0.0010 (12)
  C11   0.0245 (9)    0.0192 (9)    0.0173 (8)    0.0018 (7)     0.0029 (7)      0.0011 (7)
  C12   0.0245 (9)    0.0241 (10)   0.0270 (9)    0.0061 (8)     −0.0013 (8)     −0.0026 (8)
  C13   0.0212 (9)    0.0328 (11)   0.0279 (10)   0.0015 (8)     −0.0011 (7)     0.0008 (8)
  C14   0.0278 (10)   0.0268 (11)   0.0296 (10)   −0.0080 (8)    0.0059 (8)      −0.0019 (8)
  C15   0.0298 (10)   0.0187 (10)   0.0453 (12)   −0.0004 (8)    0.0107 (9)      −0.0025 (9)
  C16   0.0233 (9)    0.0190 (10)   0.0347 (10)   0.0017 (8)     0.0069 (8)      −0.0005 (8)
  C21   0.0203 (9)    0.0204 (9)    0.0215 (9)    0.0019 (7)     −0.0024 (7)     0.0036 (7)
  C22   0.0260 (10)   0.0203 (10)   0.0320 (10)   −0.0032 (8)    −0.0037 (8)     0.0013 (8)
  C23   0.0235 (10)   0.0288 (11)   0.0396 (11)   −0.0078 (8)    −0.0012 (8)     0.0090 (9)
  C24   0.0230 (10)   0.0387 (12)   0.0325 (11)   −0.0006 (9)    0.0051 (8)      0.0097 (9)
  C25   0.0276 (10)   0.0297 (11)   0.0258 (10)   −0.0019 (8)    0.0006 (8)      0.0010 (8)
  C26   0.0206 (9)    0.0224 (9)    0.0227 (9)    −0.0032 (7)    −0.0004 (7)     0.0022 (7)
  C31   0.0226 (9)    0.0154 (9)    0.0318 (10)   0.0013 (7)     −0.0053 (8)     −0.0033 (7)
  C32   0.0284 (10)   0.0207 (10)   0.0366 (11)   0.0016 (8)     −0.0022 (8)     −0.0044 (8)
  C33   0.0245 (10)   0.0270 (11)   0.0534 (13)   0.0010 (9)     −0.0018 (9)     −0.0144 (10)
  C34   0.0263 (10)   0.0179 (10)   0.0621 (15)   0.0029 (8)     −0.0139 (10)    −0.0059 (10)
  C35   0.0306 (11)   0.0205 (10)   0.0481 (13)   −0.0019 (9)    −0.0140 (10)    0.0033 (9)
  C36   0.0247 (9)    0.0201 (10)   0.0331 (10)   −0.0016 (8)    −0.0099 (8)     −0.0001 (8)
  ----- ------------- ------------- ------------- -------------- --------------- ---------------

(*N*,*N*-Diallyldithiocarbamato-κ^2^*S*,*S*\')\\ triphenyltin(IV) (I). Geometric parameters (Å, º) {#d1e1903}
==================================================================================================

  ----------------------- -------------- ----------------------- --------------
  Sn---C21                2.130 (2)      C13---H13               0.9500
  Sn---C11                2.1427 (19)    C14---C15               1.393 (3)
  Sn---C31                2.1673 (19)    C14---H14               0.9500
  Sn---S1                 2.4749 (4)     C15---C16               1.386 (3)
  Sn---S2                 2.9456 (5)     C15---H15               0.9500
  S1---C1                 1.7559 (19)    C16---H16               0.9500
  S2---C1                 1.6894 (19)    C21---C26               1.394 (3)
  N1---C1                 1.330 (3)      C21---C22               1.395 (3)
  N1---C2                 1.468 (3)      C22---C23               1.384 (3)
  N1---C5                 1.477 (2)      C22---H22               0.9500
  C2---C3                 1.502 (3)      C23---C24               1.385 (3)
  C2---H2A                0.9900         C23---H23               0.9500
  C2---H2B                0.9900         C24---C25               1.388 (3)
  C3---C4                 1.317 (3)      C24---H24               0.9500
  C3---H3                 0.9500         C25---C26               1.387 (3)
  C4---H4A                0.9500         C25---H25               0.9500
  C4---H4B                0.9500         C26---H26               0.9500
  C5---C6                 1.493 (3)      C31---C32               1.395 (3)
  C5---H5A                0.9900         C31---C36               1.401 (3)
  C5---H5B                0.9900         C32---C33               1.392 (3)
  C6---C7                 1.315 (3)      C32---H32               0.9500
  C6---H6                 0.9500         C33---C34               1.388 (4)
  C7---H7A                0.9500         C33---H33               0.9500
  C7---H7B                0.9500         C34---C35               1.373 (4)
  C11---C12               1.393 (3)      C34---H34               0.9500
  C11---C16               1.393 (3)      C35---C36               1.393 (3)
  C12---C13               1.390 (3)      C35---H35               0.9500
  C12---H12               0.9500         C36---H36               0.9500
  C13---C14               1.379 (3)                              
                                                                 
  C21---Sn---C11          111.15 (7)     C14---C13---C12         119.99 (18)
  C21---Sn---C31          107.13 (7)     C14---C13---H13         120.0
  C11---Sn---C31          104.14 (7)     C12---C13---H13         120.0
  C21---Sn---S1           110.28 (5)     C13---C14---C15         119.53 (19)
  C11---Sn---S1           128.76 (5)     C13---C14---H14         120.2
  C31---Sn---S1           91.01 (5)      C15---C14---H14         120.2
  C21---Sn---S2           86.57 (5)      C16---C15---C14         120.43 (19)
  C11---Sn---S2           88.36 (5)      C16---C15---H15         119.8
  C31---Sn---S2           156.01 (5)     C14---C15---H15         119.8
  S1---Sn---S2            65.470 (14)    C15---C16---C11         120.48 (18)
  C1---S1---Sn            94.89 (7)      C15---C16---H16         119.8
  C1---S2---Sn            80.86 (6)      C11---C16---H16         119.8
  C1---N1---C2            123.08 (16)    C26---C21---C22         118.46 (19)
  C1---N1---C5            121.51 (16)    C26---C21---Sn          119.19 (14)
  C2---N1---C5            115.39 (15)    C22---C21---Sn          122.33 (15)
  N1---C1---S2            123.75 (14)    C23---C22---C21         120.87 (19)
  N1---C1---S1            117.96 (14)    C23---C22---H22         119.6
  S2---C1---S1            118.29 (11)    C21---C22---H22         119.6
  N1---C2---C3            112.04 (17)    C22---C23---C24         120.03 (19)
  N1---C2---H2A           109.2          C22---C23---H23         120.0
  C3---C2---H2A           109.2          C24---C23---H23         120.0
  N1---C2---H2B           109.2          C23---C24---C25         119.9 (2)
  C3---C2---H2B           109.2          C23---C24---H24         120.1
  H2A---C2---H2B          107.9          C25---C24---H24         120.1
  C4---C3---C2            125.52 (19)    C26---C25---C24         119.9 (2)
  C4---C3---H3            117.2          C26---C25---H25         120.0
  C2---C3---H3            117.2          C24---C25---H25         120.0
  C3---C4---H4A           120.0          C25---C26---C21         120.81 (18)
  C3---C4---H4B           120.0          C25---C26---H26         119.6
  H4A---C4---H4B          120.0          C21---C26---H26         119.6
  N1---C5---C6            110.80 (17)    C32---C31---C36         118.31 (19)
  N1---C5---H5A           109.5          C32---C31---Sn          121.84 (15)
  C6---C5---H5A           109.5          C36---C31---Sn          119.85 (15)
  N1---C5---H5B           109.5          C31---C32---C33         121.0 (2)
  C6---C5---H5B           109.5          C31---C32---H32         119.5
  H5A---C5---H5B          108.1          C33---C32---H32         119.5
  C7---C6---C5            124.0 (2)      C34---C33---C32         119.6 (2)
  C7---C6---H6            118.0          C34---C33---H33         120.2
  C5---C6---H6            118.0          C32---C33---H33         120.2
  C6---C7---H7A           120.0          C35---C34---C33         120.4 (2)
  C6---C7---H7B           120.0          C35---C34---H34         119.8
  H7A---C7---H7B          120.0          C33---C34---H34         119.8
  C12---C11---C16         118.46 (18)    C34---C35---C36         120.2 (2)
  C12---C11---Sn          118.09 (14)    C34---C35---H35         119.9
  C16---C11---Sn          123.03 (14)    C36---C35---H35         119.9
  C13---C12---C11         121.09 (19)    C35---C36---C31         120.5 (2)
  C13---C12---H12         119.5          C35---C36---H36         119.7
  C11---C12---H12         119.5          C31---C36---H36         119.7
                                                                 
  C2---N1---C1---S2       −177.36 (15)   C14---C15---C16---C11   0.1 (3)
  C5---N1---C1---S2       0.8 (3)        C12---C11---C16---C15   0.3 (3)
  C2---N1---C1---S1       2.3 (3)        Sn---C11---C16---C15    −172.13 (15)
  C5---N1---C1---S1       −179.62 (14)   C26---C21---C22---C23   0.2 (3)
  Sn---S2---C1---N1       −174.18 (18)   Sn---C21---C22---C23    178.75 (15)
  Sn---S2---C1---S1       6.21 (10)      C21---C22---C23---C24   −0.3 (3)
  Sn---S1---C1---N1       173.04 (15)    C22---C23---C24---C25   0.0 (3)
  Sn---S1---C1---S2       −7.33 (12)     C23---C24---C25---C26   0.4 (3)
  C1---N1---C2---C3       91.6 (2)       C24---C25---C26---C21   −0.5 (3)
  C5---N1---C2---C3       −86.6 (2)      C22---C21---C26---C25   0.2 (3)
  N1---C2---C3---C4       −4.2 (3)       Sn---C21---C26---C25    −178.38 (15)
  C1---N1---C5---C6       95.9 (2)       C36---C31---C32---C33   −0.3 (3)
  C2---N1---C5---C6       −85.9 (2)      Sn---C31---C32---C33    −179.70 (14)
  N1---C5---C6---C7       118.2 (2)      C31---C32---C33---C34   −0.2 (3)
  C16---C11---C12---C13   −0.3 (3)       C32---C33---C34---C35   0.3 (3)
  Sn---C11---C12---C13    172.55 (15)    C33---C34---C35---C36   0.0 (3)
  C11---C12---C13---C14   −0.2 (3)       C34---C35---C36---C31   −0.4 (3)
  C12---C13---C14---C15   0.6 (3)        C32---C31---C36---C35   0.6 (3)
  C13---C14---C15---C16   −0.5 (3)       Sn---C31---C36---C35    −179.98 (14)
  ----------------------- -------------- ----------------------- --------------

(*N*,*N*-Diallyldithiocarbamato-κ^2^*S*,*S*\')\\ triphenyltin(IV) (I). Hydrogen-bond geometry (Å, º) {#d1e2838}
====================================================================================================

*Cg*1 and *Cg*2 are the centroids of the (C21--C26) and (C31--C36) rings, respectively.

  ----------------------- --------- --------- ----------- ---------------
  *D*---H···*A*           *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C13---H13···*Cg*1^i^    0.95      2.92      3.605 (2)   130
  C23---H23···*Cg*2^ii^   0.95      2.99      3.720 (3)   134
  ----------------------- --------- --------- ----------- ---------------

Symmetry codes: (i) *x*−1, *y*, *z*; (ii) *x*+1, *y*, *z*.

Bis(*N*,*N*-diallyldithiocarbamato-κ^2^*S*,*S*\')diphenyltin(IV) (II). Crystal data {#d1e2979}
===================================================================================

  ---------------------------------------- ----------------------------------------
  \[Sn(C~6~H~5~)~2~(C~7~H~10~NS~2~)~2~\]   *F*(000) = 2512
  *M~r~* = 617.45                          *D*~x~ = 1.484 Mg m^−3^
  Monoclinic, *P*2~1~/*c*                  Cu *K*α radiation, λ = 1.54184 Å
  *a* = 9.6160 (1) Å                       Cell parameters from 40535 reflections
  *b* = 30.4216 (2) Å                      θ = 2.9--76.3°
  *c* = 19.1928 (1) Å                      µ = 10.30 mm^−1^
  β = 100.019 (1)°                         *T* = 100 K
  *V* = 5528.93 (8) Å^3^                   Prism, colourless
  *Z* = 8                                  0.19 × 0.14 × 0.07 mm
  ---------------------------------------- ----------------------------------------

Bis(*N*,*N*-diallyldithiocarbamato-κ^2^*S*,*S*\')diphenyltin(IV) (II). Data collection {#d1e3116}
======================================================================================

  ------------------------------------------------------------------------------ --------------------------------------
  XtaLAB Synergy, Dualflex, AtlasS2 diffractometer                               9876 independent reflections
  Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source   9370 reflections with *I* \> 2σ(*I*)
  Mirror monochromator                                                           *R*~int~ = 0.037
  Detector resolution: 5.2558 pixels mm^-1^                                      θ~max~ = 67.1°, θ~min~ = 3.7°
  ω scans                                                                        *h* = −11→11
  Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2018)                 *k* = −36→25
  *T*~min~ = 0.633, *T*~max~ = 1.000                                             *l* = −22→22
  67735 measured reflections                                                     
  ------------------------------------------------------------------------------ --------------------------------------

Bis(*N*,*N*-diallyldithiocarbamato-κ^2^*S*,*S*\')diphenyltin(IV) (II). Refinement {#d1e3233}
=================================================================================

  ------------------------------------- -------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.027   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.068                  H-atom parameters constrained
  *S* = 1.01                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0362*P*)^2^ + 7.0312*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  9876 reflections                      (Δ/σ)~max~ = 0.003
  595 parameters                        Δρ~max~ = 1.23 e Å^−3^
  0 restraints                          Δρ~min~ = −0.73 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------------------

Bis(*N*,*N*-diallyldithiocarbamato-κ^2^*S*,*S*\')diphenyltin(IV) (II). Special details {#d1e3389}
======================================================================================

  -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
  Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
  -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

Bis(*N*,*N*-diallyldithiocarbamato-κ^2^*S*,*S*\')diphenyltin(IV) (II). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#d1e3408}
=========================================================================================================================================================================

  ------ ------------- -------------- -------------- -------------------- --
         *x*           *y*            *z*            *U*~iso~\*/*U*~eq~   
  Sn1    0.96840 (2)   0.26758 (2)    0.60783 (2)    0.01863 (5)          
  S1     1.05093 (7)   0.34237 (2)    0.65910 (3)    0.02202 (13)         
  S2     1.05034 (7)   0.32188 (2)    0.50854 (3)    0.02481 (13)         
  S3     0.82312 (7)   0.21606 (2)    0.51668 (4)    0.02761 (14)         
  S4     0.71629 (7)   0.30174 (2)    0.55382 (3)    0.02345 (13)         
  N1     1.1264 (2)    0.39971 (7)    0.56894 (11)   0.0203 (4)           
  N2     0.5656 (2)    0.24617 (7)    0.46333 (12)   0.0253 (5)           
  C1     1.0824 (2)    0.35895 (8)    0.57638 (13)   0.0189 (5)           
  C2     1.1517 (3)    0.41701 (9)    0.50102 (14)   0.0251 (6)           
  H2A    1.121986      0.448186       0.496767       0.030\*              
  H2B    1.093159      0.400473       0.462164       0.030\*              
  C3     1.3039 (3)    0.41377 (9)    0.49308 (14)   0.0286 (6)           
  H3     1.331520      0.429629       0.455081       0.034\*              
  C4     1.4027 (3)    0.39104 (10)   0.53379 (16)   0.0309 (6)           
  H4A    1.380189      0.374657       0.572463       0.037\*              
  H4B    1.496585      0.391033       0.524485       0.037\*              
  C5     1.1518 (3)    0.43140 (8)    0.62834 (14)   0.0225 (5)           
  H5A    1.229774      0.451427       0.621918       0.027\*              
  H5B    1.180874      0.415255       0.673303       0.027\*              
  C6     1.0221 (3)    0.45784 (9)    0.63244 (13)   0.0246 (5)           
  H6     0.938442      0.442486       0.637625       0.030\*              
  C7     1.0169 (3)    0.50095 (10)   0.62931 (15)   0.0312 (6)           
  H7A    1.098766      0.517238       0.624141       0.037\*              
  H7B    0.931250      0.515847       0.632218       0.037\*              
  C8     0.6860 (3)    0.25402 (8)    0.50603 (13)   0.0211 (5)           
  C9     0.4473 (3)    0.27826 (9)    0.45194 (15)   0.0270 (6)           
  H9A    0.459611      0.299926       0.491021       0.032\*              
  H9B    0.356671      0.262729       0.451561       0.032\*              
  C10    0.4444 (3)    0.30145 (11)   0.38295 (16)   0.0357 (7)           
  H10    0.513805      0.323315       0.380204       0.043\*              
  C11    0.3516 (4)    0.29318 (13)   0.32636 (18)   0.0485 (9)           
  H11A   0.281054      0.271475       0.327679       0.058\*              
  H11B   0.354463      0.308876       0.283842       0.058\*              
  C12    0.5396 (3)    0.20533 (10)   0.42143 (16)   0.0341 (7)           
  H12A   0.630727      0.190610       0.419544       0.041\*              
  H12B   0.494638      0.212628       0.372403       0.041\*              
  C13    0.4460 (4)    0.17484 (10)   0.45334 (18)   0.0415 (8)           
  H13    0.483016      0.161495       0.497427       0.050\*              
  C14    0.3162 (4)    0.16547 (13)   0.4240 (3)     0.0601 (11)          
  H14A   0.276367      0.178312       0.379956       0.072\*              
  H14B   0.261771      0.145828       0.446853       0.072\*              
  C15    1.1604 (3)    0.22965 (8)    0.61670 (13)   0.0210 (5)           
  C16    1.2902 (3)    0.24774 (9)    0.60881 (14)   0.0247 (5)           
  H16    1.295812      0.277867       0.596567       0.030\*              
  C17    1.4111 (3)    0.22188 (9)    0.61878 (16)   0.0289 (6)           
  H17    1.499314      0.234539       0.614001       0.035\*              
  C18    1.4039 (3)    0.17786 (9)    0.63562 (14)   0.0273 (6)           
  H18    1.486760      0.160247       0.641839       0.033\*              
  C19    1.2754 (3)    0.15942 (9)    0.64342 (14)   0.0256 (6)           
  H19    1.270001      0.129177       0.654966       0.031\*              
  C20    1.1552 (3)    0.18534 (9)    0.63427 (13)   0.0230 (5)           
  H20    1.067687      0.172668       0.640090       0.028\*              
  C21    0.8975 (3)    0.24718 (8)    0.70441 (13)   0.0203 (5)           
  C22    0.9742 (3)    0.26067 (9)    0.76923 (14)   0.0265 (6)           
  H22    1.055704      0.278445       0.770037       0.032\*              
  C23    0.9342 (3)    0.24871 (10)   0.83264 (15)   0.0323 (6)           
  H23    0.988359      0.258258       0.876175       0.039\*              
  C24    0.8158 (3)    0.22295 (10)   0.83270 (16)   0.0317 (6)           
  H24    0.787943      0.214921       0.876082       0.038\*              
  C25    0.7383 (3)    0.20897 (10)   0.76898 (16)   0.0327 (6)           
  H25    0.656701      0.191282       0.768520       0.039\*              
  C26    0.7797 (3)    0.22080 (9)    0.70546 (15)   0.0266 (6)           
  H26    0.726533      0.210653       0.662062       0.032\*              
  Sn2    0.42934 (2)   0.47935 (2)    0.26224 (2)    0.01967 (5)          
  S1A    0.50653 (7)   0.43729 (2)    0.15999 (3)    0.02630 (14)         
  S2A    0.65505 (7)   0.51843 (2)    0.21454 (3)    0.02630 (14)         
  S3A    0.39019 (7)   0.55322 (2)    0.32085 (3)    0.02589 (14)         
  S4A    0.29651 (7)   0.53675 (2)    0.16787 (3)    0.02586 (14)         
  N1A    0.6984 (2)    0.47703 (7)    0.09775 (12)   0.0264 (5)           
  N2A    0.2774 (2)    0.61450 (7)    0.22935 (11)   0.0229 (4)           
  C1A    0.6292 (3)    0.47819 (8)    0.15187 (14)   0.0234 (5)           
  C2A    0.6696 (3)    0.44435 (10)   0.03990 (15)   0.0328 (6)           
  H2A1   0.675651      0.458786       −0.005706      0.039\*              
  H2A2   0.572710      0.432678       0.037076       0.039\*              
  C3A    0.7733 (4)    0.40729 (10)   0.05215 (16)   0.0375 (7)           
  H3A    0.763123      0.386079       0.087245       0.045\*              
  C4A    0.8781 (4)    0.40263 (11)   0.01660 (17)   0.0400 (7)           
  H4A1   0.890527      0.423401       −0.018758      0.048\*              
  H4A2   0.941186      0.378490       0.026373       0.048\*              
  C5A    0.8112 (3)    0.50881 (10)   0.09071 (15)   0.0280 (6)           
  H5A1   0.888230      0.493556       0.072253       0.034\*              
  H5A2   0.850815      0.520988       0.137826       0.034\*              
  C6A    0.7561 (4)    0.54519 (12)   0.04217 (19)   0.0446 (8)           
  H6A    0.688042      0.564544       0.055802       0.053\*              
  C7A    0.7971 (5)    0.55184 (17)   −0.0189 (2)    0.0720 (15)          
  H7A1   0.865062      0.532902       −0.033670      0.086\*              
  H7A2   0.758874      0.575581       −0.048313      0.086\*              
  C8A    0.3158 (3)    0.57268 (8)    0.23782 (13)   0.0221 (5)           
  C9A    0.2113 (3)    0.63244 (9)    0.16070 (14)   0.0254 (6)           
  H9A1   0.250124      0.617093       0.122830       0.030\*              
  H9A2   0.236138      0.663945       0.158775       0.030\*              
  C10A   0.0529 (3)    0.62794 (9)    0.14665 (14)   0.0270 (6)           
  H10A   0.003035      0.643092       0.106705       0.032\*              
  C11A   −0.0226 (3)   0.60500 (9)    0.18449 (15)   0.0296 (6)           
  H11C   0.022624      0.589294       0.224927       0.036\*              
  H11D   −0.122521     0.604126       0.171420       0.036\*              
  C12A   0.3060 (3)    0.64644 (9)    0.28729 (15)   0.0262 (6)           
  H12C   0.306030      0.631114       0.332786       0.031\*              
  H12D   0.229511      0.668611       0.281445       0.031\*              
  C13A   0.4451 (3)    0.66935 (9)    0.28974 (15)   0.0304 (6)           
  H13A   0.461271      0.694727       0.318873       0.036\*              
  C14A   0.5464 (3)    0.65786 (11)   0.25573 (16)   0.0345 (7)           
  H14C   0.535363      0.632722       0.225908       0.041\*              
  H14D   0.630812      0.674669       0.260903       0.041\*              
  C15A   0.5755 (3)    0.45369 (8)    0.35224 (13)   0.0199 (5)           
  C16A   0.6517 (3)    0.41536 (9)    0.34627 (15)   0.0262 (6)           
  H16A   0.641902      0.400827       0.301871       0.031\*              
  C17A   0.7420 (3)    0.39798 (9)    0.40436 (16)   0.0281 (6)           
  H17A   0.792462      0.371612       0.399584       0.034\*              
  C18A   0.7580 (3)    0.41916 (9)    0.46894 (15)   0.0267 (6)           
  H18A   0.819483      0.407280       0.508595       0.032\*              
  C19A   0.6849 (3)    0.45768 (9)    0.47610 (14)   0.0263 (6)           
  H19A   0.696848      0.472399       0.520395       0.032\*              
  C20A   0.5935 (3)    0.47474 (9)    0.41787 (14)   0.0222 (5)           
  H20A   0.542863      0.501025       0.422959       0.027\*              
  C21A   0.2380 (3)    0.44192 (9)    0.26420 (13)   0.0219 (5)           
  C22A   0.2467 (3)    0.40539 (9)    0.30792 (14)   0.0263 (6)           
  H22A   0.335183      0.397555       0.335339       0.032\*              
  C23A   0.1275 (3)    0.37983 (10)   0.31248 (16)   0.0322 (6)           
  H23A   0.135091      0.355207       0.343351       0.039\*              
  C24A   −0.0010 (3)   0.39055 (10)   0.27192 (16)   0.0330 (6)           
  H24A   −0.082123     0.373216       0.274518       0.040\*              
  C25A   −0.0111 (3)   0.42636 (11)   0.22781 (17)   0.0387 (7)           
  H25A   −0.099646     0.433692       0.199882       0.046\*              
  C26A   0.1072 (3)    0.45212 (10)   0.22356 (16)   0.0333 (6)           
  H26A   0.098571      0.476793       0.192762       0.040\*              
  ------ ------------- -------------- -------------- -------------------- --

Bis(*N*,*N*-diallyldithiocarbamato-κ^2^*S*,*S*\')diphenyltin(IV) (II). Atomic displacement parameters (Å^2^) {#d1e4989}
============================================================================================================

  ------ ------------- ------------- ------------- -------------- -------------- --------------
         *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  Sn1    0.01673 (9)   0.01771 (9)   0.02066 (9)   0.00008 (6)    0.00108 (6)    0.00380 (6)
  S1     0.0246 (3)    0.0185 (3)    0.0228 (3)    −0.0030 (2)    0.0037 (2)     0.0032 (2)
  S2     0.0267 (3)    0.0227 (3)    0.0238 (3)    0.0006 (2)     0.0011 (2)     −0.0032 (2)
  S3     0.0280 (3)    0.0230 (3)    0.0299 (3)    0.0049 (3)     −0.0003 (3)    −0.0037 (3)
  S4     0.0229 (3)    0.0177 (3)    0.0279 (3)    −0.0001 (2)    −0.0008 (2)    0.0003 (2)
  N1     0.0208 (10)   0.0202 (10)   0.0198 (10)   −0.0006 (8)    0.0031 (8)     0.0034 (8)
  N2     0.0270 (12)   0.0218 (11)   0.0267 (11)   0.0017 (9)     0.0031 (9)     −0.0053 (9)
  C1     0.0168 (11)   0.0178 (12)   0.0212 (12)   0.0021 (9)     0.0004 (9)     0.0021 (10)
  C2     0.0292 (14)   0.0255 (13)   0.0203 (13)   −0.0022 (11)   0.0035 (11)    0.0061 (10)
  C3     0.0339 (15)   0.0307 (15)   0.0231 (13)   −0.0093 (12)   0.0099 (11)    −0.0019 (11)
  C4     0.0255 (14)   0.0323 (15)   0.0362 (15)   −0.0045 (12)   0.0093 (12)    −0.0052 (12)
  C5     0.0251 (13)   0.0183 (12)   0.0236 (13)   −0.0054 (10)   0.0026 (10)    −0.0003 (10)
  C6     0.0282 (14)   0.0231 (13)   0.0218 (13)   −0.0027 (11)   0.0026 (10)    −0.0005 (10)
  C7     0.0343 (15)   0.0277 (15)   0.0315 (15)   0.0037 (12)    0.0056 (12)    0.0024 (12)
  C8     0.0230 (13)   0.0207 (12)   0.0198 (12)   0.0003 (10)    0.0046 (10)    0.0007 (10)
  C9     0.0195 (13)   0.0303 (14)   0.0299 (14)   0.0020 (11)    0.0010 (11)    −0.0008 (12)
  C10    0.0301 (15)   0.0400 (17)   0.0379 (17)   0.0053 (13)    0.0085 (13)    0.0092 (13)
  C11    0.052 (2)     0.057 (2)     0.0348 (17)   0.0146 (18)    0.0035 (15)    0.0080 (16)
  C12    0.0331 (15)   0.0317 (15)   0.0350 (16)   −0.0014 (13)   −0.0007 (12)   −0.0153 (13)
  C13    0.057 (2)     0.0245 (15)   0.0402 (17)   −0.0038 (14)   0.0013 (15)    −0.0074 (13)
  C14    0.055 (2)     0.042 (2)     0.080 (3)     −0.0198 (18)   0.004 (2)      −0.0071 (19)
  C15    0.0203 (12)   0.0222 (13)   0.0199 (12)   0.0026 (10)    0.0023 (10)    −0.0008 (10)
  C16    0.0245 (13)   0.0198 (13)   0.0304 (14)   0.0001 (11)    0.0061 (11)    0.0016 (11)
  C17    0.0225 (13)   0.0259 (14)   0.0398 (16)   0.0013 (11)    0.0091 (12)    −0.0009 (12)
  C18    0.0282 (14)   0.0237 (13)   0.0299 (14)   0.0080 (11)    0.0047 (11)    −0.0004 (11)
  C19    0.0348 (15)   0.0172 (12)   0.0244 (13)   0.0003 (11)    0.0035 (11)    0.0013 (10)
  C20    0.0223 (12)   0.0228 (13)   0.0231 (13)   −0.0025 (10)   0.0018 (10)    0.0013 (10)
  C21    0.0212 (12)   0.0168 (12)   0.0234 (12)   0.0043 (10)    0.0057 (10)    0.0053 (10)
  C22    0.0278 (14)   0.0239 (13)   0.0269 (14)   −0.0019 (11)   0.0024 (11)    0.0047 (11)
  C23    0.0414 (17)   0.0289 (15)   0.0261 (14)   0.0008 (13)    0.0043 (12)    0.0041 (12)
  C24    0.0372 (16)   0.0282 (14)   0.0332 (15)   0.0069 (12)    0.0155 (13)    0.0084 (12)
  C25    0.0284 (14)   0.0314 (15)   0.0400 (17)   −0.0041 (12)   0.0107 (12)    0.0059 (13)
  C26    0.0227 (13)   0.0284 (14)   0.0288 (14)   −0.0011 (11)   0.0049 (11)    0.0037 (11)
  Sn2    0.02228 (9)   0.01617 (9)   0.01949 (9)   0.00243 (6)    0.00069 (6)    −0.00094 (6)
  S1A    0.0294 (3)    0.0214 (3)    0.0284 (3)    −0.0055 (3)    0.0061 (3)     −0.0041 (2)
  S2A    0.0315 (3)    0.0225 (3)    0.0245 (3)    −0.0041 (3)    0.0036 (3)     −0.0031 (2)
  S3A    0.0329 (3)    0.0218 (3)    0.0211 (3)    0.0039 (3)     −0.0005 (3)    −0.0011 (2)
  S4A    0.0346 (3)    0.0196 (3)    0.0214 (3)    0.0040 (3)     −0.0007 (3)    −0.0014 (2)
  N1A    0.0283 (12)   0.0245 (12)   0.0254 (12)   −0.0052 (9)    0.0021 (9)     −0.0036 (9)
  N2A    0.0248 (11)   0.0191 (11)   0.0240 (11)   0.0014 (9)     0.0024 (9)     −0.0015 (9)
  C1A    0.0246 (13)   0.0213 (13)   0.0233 (13)   −0.0004 (10)   0.0012 (10)    0.0016 (10)
  C2A    0.0380 (16)   0.0343 (16)   0.0260 (14)   −0.0104 (13)   0.0057 (12)    −0.0071 (12)
  C3A    0.055 (2)     0.0259 (15)   0.0326 (16)   −0.0069 (14)   0.0099 (14)    −0.0063 (12)
  C4A    0.051 (2)     0.0301 (16)   0.0383 (17)   −0.0024 (14)   0.0071 (15)    −0.0092 (13)
  C5A    0.0270 (14)   0.0298 (14)   0.0267 (14)   −0.0035 (12)   0.0035 (11)    −0.0005 (11)
  C6A    0.0364 (17)   0.0426 (19)   0.050 (2)     −0.0105 (15)   −0.0057 (15)   0.0169 (16)
  C7A    0.070 (3)     0.093 (3)     0.043 (2)     −0.045 (3)     −0.0174 (19)   0.031 (2)
  C8A    0.0227 (12)   0.0203 (13)   0.0228 (12)   0.0001 (10)    0.0028 (10)    −0.0008 (10)
  C9A    0.0285 (14)   0.0210 (13)   0.0267 (13)   0.0034 (11)    0.0049 (11)    0.0049 (11)
  C10A   0.0296 (14)   0.0238 (13)   0.0260 (13)   0.0057 (11)    0.0004 (11)    −0.0008 (11)
  C11A   0.0273 (14)   0.0299 (15)   0.0303 (14)   −0.0005 (12)   0.0014 (11)    −0.0052 (12)
  C12A   0.0277 (14)   0.0214 (13)   0.0294 (14)   0.0026 (11)    0.0045 (11)    −0.0054 (11)
  C13A   0.0337 (15)   0.0235 (14)   0.0315 (15)   −0.0045 (12)   −0.0012 (12)   −0.0026 (11)
  C14A   0.0269 (14)   0.0380 (17)   0.0367 (16)   −0.0042 (13)   −0.0002 (12)   0.0035 (13)
  C15A   0.0177 (12)   0.0192 (12)   0.0217 (12)   −0.0005 (10)   0.0004 (9)     0.0022 (10)
  C16A   0.0266 (13)   0.0212 (13)   0.0292 (14)   0.0026 (11)    0.0007 (11)    −0.0024 (11)
  C17A   0.0232 (13)   0.0206 (13)   0.0388 (16)   0.0042 (11)    0.0010 (11)    0.0038 (11)
  C18A   0.0203 (13)   0.0281 (14)   0.0297 (14)   −0.0021 (11)   −0.0012 (11)   0.0095 (11)
  C19A   0.0257 (13)   0.0297 (14)   0.0235 (13)   −0.0017 (11)   0.0039 (11)    0.0033 (11)
  C20A   0.0204 (12)   0.0216 (13)   0.0253 (13)   0.0019 (10)    0.0059 (10)    0.0009 (10)
  C21A   0.0221 (12)   0.0227 (13)   0.0205 (12)   0.0006 (10)    0.0026 (10)    −0.0055 (10)
  C22A   0.0244 (13)   0.0266 (14)   0.0275 (14)   0.0021 (11)    0.0035 (11)    −0.0011 (11)
  C23A   0.0318 (15)   0.0294 (15)   0.0369 (16)   −0.0001 (12)   0.0105 (12)    0.0019 (12)
  C24A   0.0273 (14)   0.0362 (16)   0.0364 (16)   −0.0063 (12)   0.0078 (12)    −0.0089 (13)
  C25A   0.0226 (14)   0.0458 (19)   0.0436 (18)   0.0012 (13)    −0.0062 (13)   −0.0012 (15)
  C26A   0.0282 (15)   0.0342 (16)   0.0349 (16)   0.0012 (12)    −0.0022 (12)   0.0031 (13)
  ------ ------------- ------------- ------------- -------------- -------------- --------------

Bis(*N*,*N*-diallyldithiocarbamato-κ^2^*S*,*S*\')diphenyltin(IV) (II). Geometric parameters (Å, º) {#d1e6191}
==================================================================================================

  ----------------------- -------------- --------------------------- --------------
  Sn1---C15               2.159 (3)      Sn2---C21A                  2.170 (3)
  Sn1---C21               2.174 (2)      Sn2---C15A                  2.173 (2)
  Sn1---S1                2.5501 (6)     Sn2---S1A                   2.5585 (7)
  Sn1---S3                2.5726 (7)     Sn2---S3A                   2.5700 (6)
  Sn1---S4                2.6754 (6)     Sn2---S4A                   2.6750 (6)
  Sn1---S2                2.7393 (7)     Sn2---S2A                   2.7664 (7)
  S1---C1                 1.742 (3)      S1A---C1A                   1.740 (3)
  S2---C1                 1.710 (3)      S2A---C1A                   1.704 (3)
  S3---C8                 1.738 (3)      S3A---C8A                   1.733 (3)
  S4---C8                 1.715 (3)      S4A---C8A                   1.716 (3)
  N1---C1                 1.326 (3)      N1A---C1A                   1.328 (4)
  N1---C2                 1.465 (3)      N1A---C5A                   1.477 (4)
  N1---C5                 1.481 (3)      N1A---C2A                   1.480 (3)
  N2---C8                 1.318 (3)      N2A---C8A                   1.327 (3)
  N2---C12                1.477 (3)      N2A---C9A                   1.465 (3)
  N2---C9                 1.486 (3)      N2A---C12A                  1.466 (3)
  C2---C3                 1.500 (4)      C2A---C3A                   1.496 (5)
  C2---H2A                0.9900         C2A---H2A1                  0.9900
  C2---H2B                0.9900         C2A---H2A2                  0.9900
  C3---C4                 1.317 (4)      C3A---C4A                   1.320 (5)
  C3---H3                 0.9500         C3A---H3A                   0.9500
  C4---H4A                0.9500         C4A---H4A1                  0.9500
  C4---H4B                0.9500         C4A---H4A2                  0.9500
  C5---C6                 1.498 (4)      C5A---C6A                   1.484 (4)
  C5---H5A                0.9900         C5A---H5A1                  0.9900
  C5---H5B                0.9900         C5A---H5A2                  0.9900
  C6---C7                 1.314 (4)      C6A---C7A                   1.317 (6)
  C6---H6                 0.9500         C6A---H6A                   0.9500
  C7---H7A                0.9500         C7A---H7A1                  0.9500
  C7---H7B                0.9500         C7A---H7A2                  0.9500
  C9---C10                1.496 (4)      C9A---C10A                  1.506 (4)
  C9---H9A                0.9900         C9A---H9A1                  0.9900
  C9---H9B                0.9900         C9A---H9A2                  0.9900
  C10---C11               1.305 (5)      C10A---C11A                 1.314 (4)
  C10---H10               0.9500         C10A---H10A                 0.9500
  C11---H11A              0.9500         C11A---H11C                 0.9500
  C11---H11B              0.9500         C11A---H11D                 0.9500
  C12---C13               1.496 (5)      C12A---C13A                 1.501 (4)
  C12---H12A              0.9900         C12A---H12C                 0.9900
  C12---H12B              0.9900         C12A---H12D                 0.9900
  C13---C14               1.308 (5)      C13A---C14A                 1.311 (4)
  C13---H13               0.9500         C13A---H13A                 0.9500
  C14---H14A              0.9500         C14A---H14C                 0.9500
  C14---H14B              0.9500         C14A---H14D                 0.9500
  C15---C20               1.392 (4)      C15A---C16A                 1.393 (4)
  C15---C16               1.396 (4)      C15A---C20A                 1.397 (4)
  C16---C17               1.390 (4)      C16A---C17A                 1.393 (4)
  C16---H16               0.9500         C16A---H16A                 0.9500
  C17---C18               1.382 (4)      C17A---C18A                 1.382 (4)
  C17---H17               0.9500         C17A---H17A                 0.9500
  C18---C19               1.389 (4)      C18A---C19A                 1.386 (4)
  C18---H18               0.9500         C18A---H18A                 0.9500
  C19---C20               1.385 (4)      C19A---C20A                 1.396 (4)
  C19---H19               0.9500         C19A---H19A                 0.9500
  C20---H20               0.9500         C20A---H20A                 0.9500
  C21---C26               1.391 (4)      C21A---C22A                 1.386 (4)
  C21---C22               1.393 (4)      C21A---C26A                 1.395 (4)
  C22---C23               1.387 (4)      C22A---C23A                 1.400 (4)
  C22---H22               0.9500         C22A---H22A                 0.9500
  C23---C24               1.382 (4)      C23A---C24A                 1.380 (4)
  C23---H23               0.9500         C23A---H23A                 0.9500
  C24---C25               1.384 (4)      C24A---C25A                 1.373 (5)
  C24---H24               0.9500         C24A---H24A                 0.9500
  C25---C26               1.394 (4)      C25A---C26A                 1.396 (4)
  C25---H25               0.9500         C25A---H25A                 0.9500
  C26---H26               0.9500         C26A---H26A                 0.9500
                                                                     
  C15---Sn1---C21         99.84 (9)      C21A---Sn2---C15A           103.34 (9)
  C15---Sn1---S1          104.01 (7)     C21A---Sn2---S1A            96.36 (7)
  C21---Sn1---S1          92.77 (7)      C15A---Sn2---S1A            101.31 (7)
  C15---Sn1---S3          94.80 (7)      C21A---Sn2---S3A            105.20 (7)
  C21---Sn1---S3          101.09 (7)     C15A---Sn2---S3A            95.16 (7)
  S1---Sn1---S3           154.38 (2)     S1A---Sn2---S3A             149.00 (2)
  C15---Sn1---S4          160.59 (7)     C21A---Sn2---S4A            92.74 (7)
  C21---Sn1---S4          92.52 (7)      C15A---Sn2---S4A            159.91 (7)
  S1---Sn1---S4           90.18 (2)      S1A---Sn2---S4A             88.58 (2)
  S3---Sn1---S4           67.97 (2)      S3A---Sn2---S4A             68.69 (2)
  C15---Sn1---S2          91.81 (7)      C21A---Sn2---S2A            161.40 (7)
  C21---Sn1---S2          159.42 (7)     C15A---Sn2---S2A            88.92 (7)
  S1---Sn1---S2           67.824 (19)    S1A---Sn2---S2A             67.18 (2)
  S3---Sn1---S2           94.71 (2)      S3A---Sn2---S2A             87.26 (2)
  S4---Sn1---S2           81.21 (2)      S4A---Sn2---S2A             78.76 (2)
  C1---S1---Sn1           89.92 (8)      C1A---S1A---Sn2             90.15 (9)
  C1---S2---Sn1           84.47 (9)      C1A---S2A---Sn2             84.16 (9)
  C8---S3---Sn1           89.22 (9)      C8A---S3A---Sn2             87.98 (9)
  C8---S4---Sn1           86.37 (9)      C8A---S4A---Sn2             84.96 (9)
  C1---N1---C2            122.5 (2)      C1A---N1A---C5A             122.0 (2)
  C1---N1---C5            122.6 (2)      C1A---N1A---C2A             123.4 (2)
  C2---N1---C5            114.9 (2)      C5A---N1A---C2A             114.5 (2)
  C8---N2---C12           122.5 (2)      C8A---N2A---C9A             122.4 (2)
  C8---N2---C9            122.6 (2)      C8A---N2A---C12A            122.1 (2)
  C12---N2---C9           114.8 (2)      C9A---N2A---C12A            115.5 (2)
  N1---C1---S2            123.62 (19)    N1A---C1A---S2A             122.7 (2)
  N1---C1---S1            118.58 (19)    N1A---C1A---S1A             119.4 (2)
  S2---C1---S1            117.77 (14)    S2A---C1A---S1A             117.94 (16)
  N1---C2---C3            112.5 (2)      N1A---C2A---C3A             110.9 (2)
  N1---C2---H2A           109.1          N1A---C2A---H2A1            109.5
  C3---C2---H2A           109.1          C3A---C2A---H2A1            109.5
  N1---C2---H2B           109.1          N1A---C2A---H2A2            109.5
  C3---C2---H2B           109.1          C3A---C2A---H2A2            109.5
  H2A---C2---H2B          107.8          H2A1---C2A---H2A2           108.1
  C4---C3---C2            126.2 (3)      C4A---C3A---C2A             123.2 (3)
  C4---C3---H3            116.9          C4A---C3A---H3A             118.4
  C2---C3---H3            116.9          C2A---C3A---H3A             118.4
  C3---C4---H4A           120.0          C3A---C4A---H4A1            120.0
  C3---C4---H4B           120.0          C3A---C4A---H4A2            120.0
  H4A---C4---H4B          120.0          H4A1---C4A---H4A2           120.0
  N1---C5---C6            111.3 (2)      N1A---C5A---C6A             110.9 (2)
  N1---C5---H5A           109.4          N1A---C5A---H5A1            109.5
  C6---C5---H5A           109.4          C6A---C5A---H5A1            109.5
  N1---C5---H5B           109.4          N1A---C5A---H5A2            109.5
  C6---C5---H5B           109.4          C6A---C5A---H5A2            109.5
  H5A---C5---H5B          108.0          H5A1---C5A---H5A2           108.0
  C7---C6---C5            124.0 (3)      C7A---C6A---C5A             122.9 (4)
  C7---C6---H6            118.0          C7A---C6A---H6A             118.5
  C5---C6---H6            118.0          C5A---C6A---H6A             118.5
  C6---C7---H7A           120.0          C6A---C7A---H7A1            120.0
  C6---C7---H7B           120.0          C6A---C7A---H7A2            120.0
  H7A---C7---H7B          120.0          H7A1---C7A---H7A2           120.0
  N2---C8---S4            122.3 (2)      N2A---C8A---S4A             121.67 (19)
  N2---C8---S3            121.3 (2)      N2A---C8A---S3A             120.11 (19)
  S4---C8---S3            116.40 (15)    S4A---C8A---S3A             118.21 (15)
  N2---C9---C10           109.6 (2)      N2A---C9A---C10A            113.2 (2)
  N2---C9---H9A           109.8          N2A---C9A---H9A1            108.9
  C10---C9---H9A          109.8          C10A---C9A---H9A1           108.9
  N2---C9---H9B           109.8          N2A---C9A---H9A2            108.9
  C10---C9---H9B          109.8          C10A---C9A---H9A2           108.9
  H9A---C9---H9B          108.2          H9A1---C9A---H9A2           107.7
  C11---C10---C9          123.4 (3)      C11A---C10A---C9A           126.1 (3)
  C11---C10---H10         118.3          C11A---C10A---H10A          117.0
  C9---C10---H10          118.3          C9A---C10A---H10A           117.0
  C10---C11---H11A        120.0          C10A---C11A---H11C          120.0
  C10---C11---H11B        120.0          C10A---C11A---H11D          120.0
  H11A---C11---H11B       120.0          H11C---C11A---H11D          120.0
  N2---C12---C13          110.8 (2)      N2A---C12A---C13A           112.3 (2)
  N2---C12---H12A         109.5          N2A---C12A---H12C           109.1
  C13---C12---H12A        109.5          C13A---C12A---H12C          109.1
  N2---C12---H12B         109.5          N2A---C12A---H12D           109.1
  C13---C12---H12B        109.5          C13A---C12A---H12D          109.1
  H12A---C12---H12B       108.1          H12C---C12A---H12D          107.9
  C14---C13---C12         123.8 (3)      C14A---C13A---C12A          126.5 (3)
  C14---C13---H13         118.1          C14A---C13A---H13A          116.7
  C12---C13---H13         118.1          C12A---C13A---H13A          116.7
  C13---C14---H14A        120.0          C13A---C14A---H14C          120.0
  C13---C14---H14B        120.0          C13A---C14A---H14D          120.0
  H14A---C14---H14B       120.0          H14C---C14A---H14D          120.0
  C20---C15---C16         118.6 (2)      C16A---C15A---C20A          118.3 (2)
  C20---C15---Sn1         118.07 (19)    C16A---C15A---Sn2           120.81 (19)
  C16---C15---Sn1         123.31 (19)    C20A---C15A---Sn2           120.91 (18)
  C17---C16---C15         120.3 (2)      C17A---C16A---C15A          121.1 (3)
  C17---C16---H16         119.8          C17A---C16A---H16A          119.5
  C15---C16---H16         119.8          C15A---C16A---H16A          119.5
  C18---C17---C16         120.4 (3)      C18A---C17A---C16A          119.8 (3)
  C18---C17---H17         119.8          C18A---C17A---H17A          120.1
  C16---C17---H17         119.8          C16A---C17A---H17A          120.1
  C19---C18---C17         119.9 (3)      C17A---C18A---C19A          120.3 (2)
  C19---C18---H18         120.1          C17A---C18A---H18A          119.9
  C17---C18---H18         120.1          C19A---C18A---H18A          119.9
  C18---C19---C20         119.7 (2)      C18A---C19A---C20A          119.7 (3)
  C18---C19---H19         120.2          C18A---C19A---H19A          120.2
  C20---C19---H19         120.2          C20A---C19A---H19A          120.2
  C19---C20---C15         121.2 (2)      C15A---C20A---C19A          120.9 (2)
  C19---C20---H20         119.4          C15A---C20A---H20A          119.6
  C15---C20---H20         119.4          C19A---C20A---H20A          119.6
  C26---C21---C22         117.6 (2)      C22A---C21A---C26A          118.0 (3)
  C26---C21---Sn1         123.63 (19)    C22A---C21A---Sn2           118.00 (19)
  C22---C21---Sn1         118.80 (19)    C26A---C21A---Sn2           124.0 (2)
  C23---C22---C21         121.4 (3)      C21A---C22A---C23A          121.3 (3)
  C23---C22---H22         119.3          C21A---C22A---H22A          119.4
  C21---C22---H22         119.3          C23A---C22A---H22A          119.4
  C24---C23---C22         120.2 (3)      C24A---C23A---C22A          119.7 (3)
  C24---C23---H23         119.9          C24A---C23A---H23A          120.1
  C22---C23---H23         119.9          C22A---C23A---H23A          120.1
  C23---C24---C25         119.4 (3)      C25A---C24A---C23A          119.7 (3)
  C23---C24---H24         120.3          C25A---C24A---H24A          120.1
  C25---C24---H24         120.3          C23A---C24A---H24A          120.1
  C24---C25---C26         120.1 (3)      C24A---C25A---C26A          120.7 (3)
  C24---C25---H25         120.0          C24A---C25A---H25A          119.7
  C26---C25---H25         120.0          C26A---C25A---H25A          119.7
  C21---C26---C25         121.3 (3)      C21A---C26A---C25A          120.5 (3)
  C21---C26---H26         119.4          C21A---C26A---H26A          119.8
  C25---C26---H26         119.4          C25A---C26A---H26A          119.8
                                                                     
  C2---N1---C1---S2       0.1 (3)        C5A---N1A---C1A---S2A       4.7 (4)
  C5---N1---C1---S2       179.23 (18)    C2A---N1A---C1A---S2A       −175.2 (2)
  C2---N1---C1---S1       −178.18 (18)   C5A---N1A---C1A---S1A       −175.4 (2)
  C5---N1---C1---S1       1.0 (3)        C2A---N1A---C1A---S1A       4.8 (4)
  Sn1---S2---C1---N1      −177.4 (2)     Sn2---S2A---C1A---N1A       172.9 (2)
  Sn1---S2---C1---S1      0.89 (13)      Sn2---S2A---C1A---S1A       −7.00 (14)
  Sn1---S1---C1---N1      177.43 (19)    Sn2---S1A---C1A---N1A       −172.4 (2)
  Sn1---S1---C1---S2      −0.95 (13)     Sn2---S1A---C1A---S2A       7.53 (15)
  C1---N1---C2---C3       −95.8 (3)      C1A---N1A---C2A---C3A       −98.2 (3)
  C5---N1---C2---C3       85.0 (3)       C5A---N1A---C2A---C3A       81.9 (3)
  N1---C2---C3---C4       12.5 (4)       N1A---C2A---C3A---C4A       −105.2 (3)
  C1---N1---C5---C6       −91.2 (3)      C1A---N1A---C5A---C6A       −97.9 (3)
  C2---N1---C5---C6       88.0 (3)       C2A---N1A---C5A---C6A       82.0 (3)
  N1---C5---C6---C7       −122.3 (3)     N1A---C5A---C6A---C7A       −114.6 (4)
  C12---N2---C8---S4      179.3 (2)      C9A---N2A---C8A---S4A       2.4 (4)
  C9---N2---C8---S4       1.2 (4)        C12A---N2A---C8A---S4A      −173.87 (19)
  C12---N2---C8---S3      −0.7 (4)       C9A---N2A---C8A---S3A       −178.66 (19)
  C9---N2---C8---S3       −178.79 (19)   C12A---N2A---C8A---S3A      5.1 (3)
  Sn1---S4---C8---N2      178.1 (2)      Sn2---S4A---C8A---N2A       175.2 (2)
  Sn1---S4---C8---S3      −1.92 (13)     Sn2---S4A---C8A---S3A       −3.74 (14)
  Sn1---S3---C8---N2      −178.1 (2)     Sn2---S3A---C8A---N2A       −175.1 (2)
  Sn1---S3---C8---S4      1.99 (14)      Sn2---S3A---C8A---S4A       3.88 (15)
  C8---N2---C9---C10      101.8 (3)      C8A---N2A---C9A---C10A      88.1 (3)
  C12---N2---C9---C10     −76.4 (3)      C12A---N2A---C9A---C10A     −95.3 (3)
  N2---C9---C10---C11     105.3 (3)      N2A---C9A---C10A---C11A     −9.9 (4)
  C8---N2---C12---C13     104.1 (3)      C8A---N2A---C12A---C13A     90.9 (3)
  C9---N2---C12---C13     −77.6 (3)      C9A---N2A---C12A---C13A     −85.6 (3)
  N2---C12---C13---C14    110.9 (4)      N2A---C12A---C13A---C14A    −13.3 (4)
  C20---C15---C16---C17   −0.4 (4)       C20A---C15A---C16A---C17A   0.9 (4)
  Sn1---C15---C16---C17   176.7 (2)      Sn2---C15A---C16A---C17A    −177.9 (2)
  C15---C16---C17---C18   0.9 (4)        C15A---C16A---C17A---C18A   −0.7 (4)
  C16---C17---C18---C19   −0.7 (4)       C16A---C17A---C18A---C19A   −0.1 (4)
  C17---C18---C19---C20   0.0 (4)        C17A---C18A---C19A---C20A   0.7 (4)
  C18---C19---C20---C15   0.6 (4)        C16A---C15A---C20A---C19A   −0.3 (4)
  C16---C15---C20---C19   −0.4 (4)       Sn2---C15A---C20A---C19A    178.47 (19)
  Sn1---C15---C20---C19   −177.60 (19)   C18A---C19A---C20A---C15A   −0.5 (4)
  C26---C21---C22---C23   −0.7 (4)       C26A---C21A---C22A---C23A   −1.2 (4)
  Sn1---C21---C22---C23   180.0 (2)      Sn2---C21A---C22A---C23A    179.5 (2)
  C21---C22---C23---C24   −0.2 (4)       C21A---C22A---C23A---C24A   1.1 (4)
  C22---C23---C24---C25   0.5 (4)        C22A---C23A---C24A---C25A   −0.4 (4)
  C23---C24---C25---C26   0.1 (4)        C23A---C24A---C25A---C26A   −0.1 (5)
  C22---C21---C26---C25   1.2 (4)        C22A---C21A---C26A---C25A   0.7 (4)
  Sn1---C21---C26---C25   −179.5 (2)     Sn2---C21A---C26A---C25A    180.0 (2)
  C24---C25---C26---C21   −0.9 (4)       C24A---C25A---C26A---C21A   −0.1 (5)
  ----------------------- -------------- --------------------------- --------------

Bis(*N*,*N*-diallyldithiocarbamato-κ^2^*S*,*S*\')diphenyltin(IV) (II). Hydrogen-bond geometry (Å, º) {#d1e8353}
====================================================================================================

*Cg*1 and *Cg*2 are the centroids of the (C15*A*--C20*A*) and (C21*A*--C26*A*) rings, respectively.

  ------------------------ --------- --------- ----------- ---------------
  *D*---H···*A*            *D*---H   H···*A*   *D*···*A*   *D*---H···*A*
  C7---H7*A*···*Cg*1^i^    0.95      2.83      3.774 (3)   172
  C7---H7*B*···*Cg*2^ii^   0.95      2.92      3.582 (3)   128
  ------------------------ --------- --------- ----------- ---------------

Symmetry codes: (i) −*x*+2, −*y*+1, −*z*+1; (ii) −*x*+1, −*y*+1, −*z*+1.

![The mol­ecular structure of (I)[](#scheme1){ref-type="chem"} showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.](e-76-00167-fig1){#fig1}

![The mol­ecular structures of the two independent mol­ecules comprising the asymmetric unit of (II)[](#scheme1){ref-type="chem"} showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.](e-76-00167-fig2){#fig2}

![Overlay diagram of the independent mol­ecules comprising the asymmetric unit of (II)[](#scheme1){ref-type="chem"}: (*a*) Sn1-containing mol­ecule (red image) and (*b*) inverted-Sn2-mol­ecule (blue). The mol­ecules are overlapped so that the (Sn1,S1,S2,C1) and (Sn2,S3,S4,C8) residues are coincident.](e-76-00167-fig3){#fig3}

![Mol­ecular packing in the crystal of (I)[](#scheme1){ref-type="chem"}: (*a*) supra­molecular chain along the *a*-axis direction sustained by phenyl-C---H⋯π(phen­yl) inter­actions shown as purple dashed lines (non-participating hydrogen atoms have been removed) and (*b*) a view of the unit-cell contents in projection down the *a* axis with one chain highlighted in space-filling mode.](e-76-00167-fig4){#fig4}

![Mol­ecular packing in the crystal of (II)[](#scheme1){ref-type="chem"}: (*a*) supra­molecular chain along the *a*-axis direction sustained by methyl­ene-C---H⋯π(phen­yl) inter­actions shown as purple dashed lines (non-participating hydrogen atoms have been removed) and (*b*) a view of the unit-cell contents in projection down the *a* axis with one chain highlighted in space-filling mode.](e-76-00167-fig5){#fig5}

![Two views of Hirshfeld surface for (I)[](#scheme1){ref-type="chem"} mapped over *d* ~norm~ in the range −0.028 to +1.257 arbitrary units.](e-76-00167-fig6){#fig6}

![Views of the Hirshfeld surfaces for (II)[](#scheme1){ref-type="chem"} mapped over *d* ~norm~ for the (*a*) and (*b*) Sn1-mol­ecule in the range −0.026 to +1.372 arbitrary units, and (*c*) and (*d*) Sn2-mol­ecule in the range −0.027 to +1.383 arbitrary units.](e-76-00167-fig7){#fig7}

![Views of Hirshfeld surfaces mapped with the shape-index property highlighting donors and acceptors of the inter­molecular C---H⋯π contacts for (*a*) and (*b*) (I)[](#scheme1){ref-type="chem"}, and (*c*) and (*d*) (II)[](#scheme1){ref-type="chem"}.](e-76-00167-fig8){#fig8}

![Views of Hirshfeld surfaces mapped over the electrostatic potential (the red and blue regions represent negative and positive electrostatic potentials, respectively) for (*a*) (I)[](#scheme1){ref-type="chem"} in the range −0.032 to +0.043 atomic units (a.u.), (*b*) the Sn1-mol­ecule in (II)[](#scheme1){ref-type="chem"} in the range −0.039 to +0.040 a.u. and (*c*) the Sn2-mol­ecule in (II)[](#scheme1){ref-type="chem"} in the range −0.038 to +0.047 a.u.](e-76-00167-fig9){#fig9}

![(*a*) A comparison of the full two-dimensional fingerprint plot for (I)[](#scheme1){ref-type="chem"} and for the Sn1- and Sn2-mol­ecules of (II)[](#scheme1){ref-type="chem"}, and those delineated into (*b*) H⋯H, (*c*) C⋯H/H⋯C and (*d*) S⋯H/H⋯S contacts.](e-76-00167-fig10){#fig10}

![The energy frameworks calculated for (I)[](#scheme1){ref-type="chem"} viewed down the *a*-axis direction showing the (*a*) electrostatic potential force, (*b*) dispersion force and (*c*) total energy. The corresponding plots for (II)[](#scheme1){ref-type="chem"}, viewed down the *a*-axis direction are shown in (*d*)--(*f*), respectively. The energy frameworks were adjusted to the same scale factor of 50 with a cut-off value of 5 kJ mol^−1^ within 2 × 2 × 2 unit cells.](e-76-00167-fig11){#fig11}

###### Selected geometric parameters (Å, °) for (I)

  Parameter        \(I\)         Parameter        \(I\)
  ---------------- ------------- ---------------- -------------
  Sn---S1          2.4749 (4)    Sn---S2          2.9456 (5)
  Sn---C11         2.1427 (19)   Sn---C21         2.130 (2)
  Sn---C31         2.1673 (19)   C1---S1          1.7559 (19)
  C1---S2          1.6894 (19)   C1---N1          1.330 (3)
                                                   
  S1---Sn---S2     65.470 (14)   C11---Sn---C21   111.15 (7)
  C11---Sn---C31   104.14 (7)    C21---Sn---C31   107.13 (7)
  S1---Sn---C11    128.76 (5)    S2---Sn---C31    156.01 (5)

###### Selected geometric parameters (Å, °) for the two independent mol­ecules in (II)

  Parameter              Sn1-mol­ecule   Sn2-mol­ecule
  ---------------------- --------------- ----------------
  Sn---S1                2.5501 (6)      2.5585 (7)
  Sn---S2                2.7393 (7)      2.7664 (7)
  Sn---S3                2.5726 (7)      2.5700 (6)
  Sn---S4                2.6754 (6)      2.6750 (6)
  C1---S1                1.742 (3)       1.740 (3)
  C1---S2                1.710 (3)       1.704 (3)
  C8---S3                1.738 (3)       1.733 (3)
  C8---S4                1.715 (3)       1.716 (3)
  C1---N1                1.326 (3)       1.328 (4)
  C8---N2                1.318 (3)       1.327 (3)
                                          
  S1---Sn---S2           67.824 (19)     67.18 (2)
  S3---Sn---S4           67.97 (2)       68.69 (2)
  S1---Sn---S3           154.38 (2)      149.00 (2)
  S2---Sn---C21          159.42 (7)      161.40 (7)
  S4---Sn---C15          160.59 (7)      159.91 (7)
  C15---Sn---C21         99.84 (9)       103.34 (9)
                                          
  N1---C2---C3---C4      12.5 (4)        9.9 (4)^*a*^
  N1---C5---C6---C7      −122.3 (3)      13.3 (4)^*a*^
  N2---C9---C10---C11    105.3 (3)       105.2 (3)^*a*^
  N2---C12---C13---C14   110.9 (4)       114.6 (4)^*a*^

Note: (*a*) for ease of comparison, the torsion angles are for the inverted Sn2-mol­ecule.

###### Hydrogen-bond geometry (Å, °) for (I)[](#scheme1){ref-type="chem"}

*Cg*1 and *Cg*2 are the centroids of the (C21--C26) and (C31--C36) rings, respectively.

  *D*---H⋯*A*           *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  --------------------- --------- ------- ----------- -------------
  C13---H13⋯*Cg*1^i^    0.95      2.92    3.605 (2)   130
  C23---H23⋯*Cg*2^ii^   0.95      2.99    3.720 (3)   134

Symmetry codes: (i) ; (ii) .

###### Hydrogen-bond geometry (Å, °) for (II)[](#scheme1){ref-type="chem"}

*Cg*1 and *Cg*2 are the centroids of the (C15*A*--C20*A*) and (C21*A*--C26*A*) rings, respectively.

  *D*---H⋯*A*            *D*---H   H⋯*A*   *D*⋯*A*     *D*---H⋯*A*
  ---------------------- --------- ------- ----------- -------------
  C7---H7*A*⋯*Cg*1^i^    0.95      2.83    3.774 (3)   172
  C7---H7*B*⋯*Cg*2^ii^   0.95      2.92    3.582 (3)   128

Symmetry codes: (i) ; (ii) .

###### Summary of short inter­atomic contacts (Å) in (I)[](#scheme1){ref-type="chem"} and (II)^*a*^

  Contact         Distance    Symmetry operation
  --------------- ----------- ---------------------------
  \(I\)                        
  C12⋯H6          2.76        −1 + *x*, *y*, *z*
  C16⋯H5*B*       2.80        1 − *x*, − *y*, 1 − *z*
  C25⋯H4*B*       2.78        *x*,  − *y*, − + *z*
  C26⋯H13         2.74        1 + *x*, *y*, *z*
  C33⋯H2*B*       2.79        1 − *x*, 1 − *y*, 1 − *z*
  H15⋯H24         2.19        1 − *x*, − + *y*,  − *z*
  S1⋯H7*B*        2.91        −1 + *x*, *y*, *z*
  S1⋯H2*A*        2.96        1 − *x*, 1 − *y*, 1 − *z*
  \(II\)                       
  S1⋯C11*A*       3.455 (3)   1 − *x*, 1 − *y*, 1 − *z*
  S4⋯C12*A*       3.473 (3)   1 − *x*, 1 − *y*, 1 − *z*
  C11⋯C23*A*      3.386 (5)   *x*, *y*, *z*
  C11⋯H23*A*      2.81        *x*, *y*, *z*
  C19⋯H11*B*      2.71        1 + *x*,  − *y*,  + *z*
  C21⋯H12*D*      2.78        1 − *x*, 1 − *y*, 1 − *z*
  H12*A*⋯H9*A*2   2.16        1 − *x*, − + *y*,  − *z*
  H17⋯H26         2.18        1 + *x*, *y*, *z*
  C4*A*⋯H9*A*1    2.75        1 − *x*, 1 − *y*, −*z*
  S1*A*⋯H18       2.91        1 − *x*,  − *y*, − + *z*
  H17⋯H13*A*      2.33        2 − *x*, 1 − *y*, 1 − *z*

Note: (*a*) The inter­atomic distances are calculated in *Crystal Explorer 17* (Turner *et al.*, 2017[@bb31]) whereby the *X*---H bond lengths are adjusted to their neutron values.

###### Percentage contributions of inter­atomic contacts to the Hirshfeld surface for (I)[](#scheme1){ref-type="chem"}, the Sn1-mol­ecule in (II)[](#scheme1){ref-type="chem"} and the Sn2-mol­ecule in (II)

  Contact     Percentage contribution                           
  ----------- ------------------------- ----------------------- -----------------------
              \(I\)                     Sn1-mol­ecule in (II)   Sn2-mol­ecule in (II)
  H⋯H         62.2                      59.9                    64.9
  C⋯H/H⋯C     28.4                      24.3                    20.1
  S⋯H/H⋯S     8.6                       14.4                    13.6
  N⋯H/H⋯ N    0.1                       0.8                     0.7
  C⋯C         0.4                       0.3                     0.1
  S⋯C/C⋯S     0.2                       0.4                     0.6
  Sn⋯H/H⋯Sn   0.1                       0.0                     0.0

###### Summary of inter­action energies (kJ mol^−1^) calculated for (I)[](#scheme1){ref-type="chem"} and (II)

  Contact                                  *R* (Å)   *E* ~ele~   *E* ~pol~   *E* ~dis~   *E* ~rep~   *E* ~tot~
  ---------------------------------------- --------- ----------- ----------- ----------- ----------- -----------
  (I)^*a*^                                                                                            
  H13⋯C26^i^ +                             8.06      −13.8       −5.6        −68.5       42.5        −45.0
  C13---H13⋯*Cg*(C21--C26)^i^ +                                                                       
  C23---H23⋯*Cg*(C31--C36)^i^ +                                                                       
  H6⋯C12^i^ +                                                                                         
  H7*B*⋯S1^i^                                                                                         
  C16 ⋯H5*B* ^ii^                          8.42      −21.8       −5.6        −52.2       29.1        −49.3
  C33 ⋯H2*B* ^iii^ +                       8.00      −21.2       −7.0        −59.2       29.5        −55.6
  S1⋯H2*A* ^iii^                                                                                      
  C25⋯H4*B* ^iv^                           9.91      −0.6        −0.8        −23.3       8.4         −15.2
  H15⋯H24^v^                               12.94     −2.6        −0.5        −12.5       9.1         −6.9
  (II)^*b*^                                                                                           
  S1⋯C11*A* ^i^ +                          8.68      −25.4       −8.6        −67.8       44.0        −57.0
  S4⋯C12*A* ^i^ +                                                                                     
  C7---H7*B*⋯*Cg*(C21*A*--C26*A*)^i^ +                                                                
  C21⋯H12*D* ^i^                                                                                      
  C4*A*⋯H9*A*1^ii^                         9.0       −28.8       −7.3        −69.0       49.0        −56.5
  C7---H7*A*⋯*Cg*(C15*A*--C20*A*)^iii^ +   9.21      −19.6       −7.4        −61.3       33.7        −52.6
  H17⋯H13*A* ^iii^                                                                                    
  H17⋯H26^iv^                              9.62      −12.0       −5.0        −51.2       25.9        −40.6
  C11⋯C23*A* ^v^                           9.93      −10.2       −2.9        −44.1       23.5        −33.0
  C11⋯H23*A* ^v^                                                                                      
  H12*A*⋯H9*A*2^vi^                        10.81     −5.9        −2.4        −30.6       14.5        −23.4
  S1*A*⋯H18^vii^                           10.11     −5.2        −3.6        −34.3       18.9        −23.
  C19⋯H11*B* ^viii^                        12.51     −7.4        −2.6        −20.5       9.8         −19.8

Notes: (*a*) Symmetry operations for (I)[](#scheme1){ref-type="chem"}: (i) −1 + *x*, *y*, *z*; (ii) 1 − *x*, − *y*, 1 − *z*; (iii) 1 − *x*, 1 − *y*, 1 − *z*; (iv) *x*  − *y*, − + *z*; (v) 1 − *x*, − + *y*,  − *z*. (*b*) Symmetry operations for (II)[](#scheme1){ref-type="chem"}: (i) 1 − *x*, 1 − *y*, 1 − *z*; (ii) 1 − *x*, 1 − *y*, − *z*; (iii) 2 − *x*, 1 − *y*, 1 − *z*; (iv) 1 + *x*, *y*, *z*; (v) *x*, *y*, *z*; (vi) 1 − *x*, − + *y*,  − *z*; (vii) 1 − *x*,  − *y*, − + *z*; (viii) 1 + *x*,  − *y*,  + *z*.

###### Experimental details

                                                                             \(I\)                                               \(II\)
  -------------------------------------------------------------------------- --------------------------------------------------- ---------------------------------------------------
  Crystal data                                                                                                                   
  Chemical formula                                                           \[Sn(C~6~H~5~)~3~(C~7~H~10~NS~2~)\]                 \[Sn(C~6~H~5~)~2~(C~7~H~10~NS~2~)~2~\]
  *M* ~r~                                                                    522.27                                              617.45
  Crystal system, space group                                                Monoclinic, *P*2~1~/*c*                             Monoclinic, *P*2~1~/*c*
  Temperature (K)                                                            100                                                 100
  *a*, *b*, *c* (Å)                                                          8.0650 (1), 11.4490 (1), 25.8775 (2)                9.6160 (1), 30.4216 (2), 19.1928 (1)
  β (°)                                                                      98.282 (1)                                          100.019 (1)
  *V* (Å^3^)                                                                 2364.51 (4)                                         5528.93 (8)
  *Z*                                                                        4                                                   8
  Radiation type                                                             Cu *K*α                                             Cu *K*α
  μ (mm^−1^)                                                                 10.32                                               10.30
  Crystal size (mm)                                                          0.13 × 0.10 × 0.04                                  0.19 × 0.14 × 0.07
                                                                                                                                 
  Data collection                                                                                                                
  Diffractometer                                                             XtaLAB Synergy, Dualflex, AtlasS2                   XtaLAB Synergy, Dualflex, AtlasS2
  Absorption correction                                                      Gaussian (*CrysAlis PRO*; Rigaku OD, 2018[@bb22])   Gaussian (*CrysAlis PRO*; Rigaku OD, 2018[@bb22])
  *T* ~min~, *T* ~max~                                                       0.807, 1.000                                        0.633, 1.000
  No. of measured, independent and observed \[*I* \> 2σ(*I*)\] reflections   55086, 4226, 4083                                   67735, 9876, 9370
  *R* ~int~                                                                  0.044                                               0.037
  (sin θ/λ)~max~ (Å^−1^)                                                     0.597                                               0.597
                                                                                                                                 
  Refinement                                                                                                                     
  *R*\[*F* ^2^ \> 2σ(*F* ^2^)\], *wR*(*F* ^2^), *S*                          0.020, 0.053, 1.01                                  0.027, 0.068, 1.02
  No. of reflections                                                         4226                                                9876
  No. of parameters                                                          262                                                 595
  H-atom treatment                                                           H-atom parameters constrained                       H-atom parameters constrained
  Δρ~max~, Δρ~min~ (e Å^−3^)                                                 0.82, −0.50                                         1.23, −0.73

Computer programs: *CrysAlis PRO* (Rigaku OD, 2018[@bb22]), *SHELXS* (Sheldrick, 2015*a* [@bb23]), *SHELXL2017/1* (Sheldrick, 2015*b* [@bb24]), *ORTEP-3 for Windows* (Farrugia, 2012[@bb6]), *DIAMOND* (Brandenburg, 2006[@bb5]) and *publCIF* (Westrip, 2010[@bb32]).

[^1]: Additional correspondence author, email: awang_normah\@yahoo.com.
