Related literature   {#sec1}
====================

For the synthesis of bpma, see: Astner *et al.* (2008[@bb1]). For the synthesis of RuCl~2~(dmso)~4~ (dmso is dimethyl sulfoxide), see: Evans *et al.* (1973[@bb6]). Ruthenium(II) complexes of pyridine-based ligands which also contain a dmso ligand act as catalytic initiators (Bressan & Morvillo, 1992[@bb2]; Carvalho *et al.*, 2014[@bb4]; Ferrer *et al.*, 2013[@bb7]). The ambidentate dmso ligand exhibits preferential binding through its S atom with low-spin *d* ^6^ Ru^II^ cations and through its O atom with Ru^III^ cations (Roeser *et al.*, 2013[@bb15]; Smith *et al.*, 2000[@bb21]). Ruthenium(II) complexes containing the labile dmso and chloride ligands are particularly attractive precursors for the synthesis of specifically designed catalysts. For the synthesis and structures of such complexes, see: Fischer *et al.* (2009[@bb8]); Mola *et al.* (2007[@bb13]). For complexes containing facially coordinated tridentate ligands, see: Dakkach *et al.* (2013[@bb5]); Fischer *et al.* (2009[@bb8]); Mishra *et al.* (2009[@bb10]); Matsuya *et al.* (2009[@bb9]); Mola *et al.* (2006[@bb12], 2007[@bb13], 2009[@bb11]); Rodriguez *et al.* (2001[@bb14]); Sala *et al.* (2008[@bb16]); Serrano *et al.* (2006[@bb17]); Shimizu *et al.* (2008[@bb20]); Suzuki *et al.* (2014[@bb22])

Experimental   {#sec2}
==============

Crystal data   {#sec2.1}
--------------

\[RuCl~2~(C~13~H~15~N~3~)(C~2~H~6~OS)\]*M* *~r~* = 463.38Monoclinic,*a* = 14.6117 (3) Å*b* = 9.3345 (2) Å*c* = 27.3451 (7) Åβ = 102.734 (1)°*V* = 3637.94 (14) Å^3^*Z* = 8Mo *K*α radiationμ = 1.28 mm^−1^*T* = 150 K0.21 × 0.17 × 0.11 mm

Data collection   {#sec2.2}
-----------------

Bruker APEXII CCD diffractometerAbsorption correction: multi-scan (*SAINT*; Bruker, 2009[@bb3]) *T* ~min~ = 0.647, *T* ~max~ = 0.74733234 measured reflections7273 independent reflections5265 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.068

Refinement   {#sec2.3}
------------

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.039*wR*(*F* ^2^) = 0.085*S* = 1.017273 reflections292 parametersAll H-atom parameters refinedΔρ~max~ = 1.13 e Å^−3^Δρ~min~ = −0.92 e Å^−3^

 {#d5e615}

Data collection: *APEX2* (Bruker, 2009[@bb3]); cell refinement: *SAINT* (Bruker, 2009[@bb3]); data reduction: *SAINT*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb18]); program(s) used to refine structure: *SHELXL2014* (Sheldrick, 2015[@bb19]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb18]); software used to prepare material for publication: *SHELXTL*.

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

Crystal structure: contains datablock(s) New_Global_Publ_Block, I. DOI: [10.1107/S2056989015014875/zq2232sup1.cif](http://dx.doi.org/10.1107/S2056989015014875/zq2232sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S2056989015014875/zq2232Isup2.hkl](http://dx.doi.org/10.1107/S2056989015014875/zq2232Isup2.hkl)

###### 

Click here for additional data file.

Structural commentary. DOI: [10.1107/S2056989015014875/zq2232sup3.docx](http://dx.doi.org/10.1107/S2056989015014875/zq2232sup3.docx)

Supporting information file. DOI: [10.1107/S2056989015014875/zq2232sup3.pdf](http://dx.doi.org/10.1107/S2056989015014875/zq2232sup3.pdf)

###### 

Click here for additional data file.

2 . DOI: [10.1107/S2056989015014875/zq2232fig1.tif](http://dx.doi.org/10.1107/S2056989015014875/zq2232fig1.tif)

View of RuCl~2~(dpma)(dmso). H atoms have been omitted and displacement parameters are drawn at the 50% probability level.

CCDC reference: [1417672](http://scripts.iucr.org/cgi-bin/cr.cgi?rm=csd&csdid=1417672)

Additional supporting information: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?zq2232&file=zq2232sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?zq2232sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?zq2232&checkcif=yes)

Supporting information for this paper is available from the IUCr electronic archives (Reference: [ZQ2232](http://scripts.iucr.org/cgi-bin/sendsup?zq2232)).

We gratefully acknowledge the University of Wyoming (AN and EBH), the Wyoming NASA Space Grant Consortium (NASA grant No. NNX10AO95H) and the National Science Foundation REU Program (KT, CHE-1358498) for financial support.

S1. Comment {#d1e22}
===========

Ruthenium(II) complexes of pyridine-based ligands which also contain a di­methyl­sulfoxide (dmso) ligand act as catalytic initiators (Bressan & Morvillo, 1992; Carvalho *et al.*, 2014; Ferrer *et al.*, 2013). The ambidentate dmso appears to show preferential binding through its S atom with Ru^II^ centers, and its O atom with Ru^III^ centers (Roeser *et al.*, 2013; Smith *et al.*, 2000). Ruthenium(II) complexes containing the labile dmso and chloride ligands are particularly attractive precursors for the synthesis of specifically-designed catalysts. Our research project is aimed at the catalytic reduction of stable anions such as perchlorates using Ru^II^ precatalysts. Multidentate ligands are expected to stabilize ruthenium(IV)--oxido inter­mediates suggested as inter­mediates in the catalytic oxidation of a variety of organic substrates in the presence of hypochlorite, perchlorate and other oxidizers (Bressan & Morvillo 1992). Here we report the X-ray crystal structural determination of a potential precursor ruthenium complex. The title compound, RuCl~2~(bpma)(dmso), is synthesized from the reaction of RuCl~2~(dmso)~4~ (Evans *et al.*, 1973 ) with *N*,*N*-bis­(pyridin-2-yl­methyl)­methyl­amine (bpma) (Astner *et al.*, 2008).

S2. Structural commentary {#d1e80}
=========================

The asymmetric unit contains a well-ordered RuCl~2~(bpma)(dmso) molecule. The metal center is in a distorted o­cta­hedral geometry with the tridentate bpma ligand binding through its two pyridyl N atoms and aliphatic N atom in a facial mode, as shown in Fig. 1. The two chloride ligands occupy two adjacent sites, and the dmso ligand is present trans to one of the pyridyl N atoms. The tridentate ligand is folded to achieve facial coordination, and the extent of folding is reflected in the small dihedral angle of 64.55 (8)° between the mean planes passing through the two pyridine rings. The two N---Ru---N bite angles of the ligand at 81.70 (7) and 82.34 (8)° are illustrative of the distorted o­cta­hedral geometry of the metal center. The complex can be represented as the *cis*,*fac*-isomer to indicate the *cis*-geometry of the dmso ligand to the aliphatic N atom and the facial coordination mode of bpma. A literature survey of Ru^II^ complexes of bpma and those of closely related bis­(pyridin-2-yl­methyl)­alkyl­amine ligands reveals that an overwhelming majority of the complexes contain facially coordinated tridentate ligands (Dakkach *et al.*, 2013; Fischer *et al.*, 2009; Mishra *et al.*, 2009; Matsuya *et al.*, 2009; Mola *et al.*, 2006, 2007, 2009; Rodriguez *et al.*, 2001; Sala *et al.*, 2008; Serrano *et al.*, 2006; Shimizu *et al.*, 2008; Suzuki *et al.*, 2014). *cis*,*fac*-isomer is the thermodynamically favored (Mola *et al.*, 2007), and therefore the more frequent occurrence of this isomer is unsurprising. However, Shimuzu *et al.* suggest that the binding mode of the tridentate ligand depends on the nature of the other ligands with the hydroxo and methoxo ligands favoring meridional coordination mode for the tridentate ligands (Shimizu *et al.*, 2008). The Ru---N~py~ distances in the present complex are unequal as they have either a chloride or dmso ligands in their respective *trans* positions. The Ru---dmso bond is unexceptional at 2.2207 (6) Å, and comparable to those found in *cis*,*fac*-RuCl~2~(bpma)(dmso) and *trans*,*mer*-RuCl~2~(bpea)(dmso) (Mola *et al.*, 2007).

Figures
=======

![View of RuCl2(dpma)(dmso). H atoms have been omitted and displacement parameters are drawn at the 50% probability level.](e-71-0m169-fig1){#Fap1}

Crystal data {#tablewrapcrystaldatalong}
============

  ----------------------------------------- ---------------------------------------
  \[RuCl~2~(C~13~H~15~N~3~)(C~2~H~6~OS)\]   *F*(000) = 1872
  *M~r~* = 463.38                           *D*~x~ = 1.692 Mg m^−3^
  Monoclinic, *C*2/*c*                      Mo *K*α radiation, λ = 0.71073 Å
  *a* = 14.6117 (3) Å                       Cell parameters from 4846 reflections
  *b* = 9.3345 (2) Å                        θ = 2.6--29.0°
  *c* = 27.3451 (7) Å                       µ = 1.28 mm^−1^
  β = 102.734 (1)°                          *T* = 150 K
  *V* = 3637.94 (14) Å^3^                   Rectangular, yellow
  *Z* = 8                                   0.21 × 0.17 × 0.11 mm
  ----------------------------------------- ---------------------------------------

Data collection {#tablewrapdatacollectionlong}
===============

  ----------------------------------------------------------- --------------------------------------
  Bruker APEXII CCD diffractometer                            5265 reflections with *I* \> 2σ(*I*)
  φ and ω scans                                               *R*~int~ = 0.068
  Absorption correction: multi-scan (*SAINT*; Bruker, 2009)   θ~max~ = 33.7°, θ~min~ = 2.6°
  *T*~min~ = 0.647, *T*~max~ = 0.747                          *h* = −19→22
  33234 measured reflections                                  *k* = −14→14
  7273 independent reflections                                *l* = −42→42
  ----------------------------------------------------------- --------------------------------------

Refinement {#tablewraprefinementdatalong}
==========

  ------------------------------------- -------------------------------------------------------------------------------------
  Refinement on *F*^2^                  0 restraints
  Least-squares matrix: full            Hydrogen site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.039   All H-atom parameters refined
  *wR*(*F*^2^) = 0.085                  *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0338*P*)^2^\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  *S* = 1.01                            (Δ/σ)~max~ = 0.002
  7273 reflections                      Δρ~max~ = 1.13 e Å^−3^
  292 parameters                        Δρ~min~ = −0.92 e Å^−3^
  ------------------------------------- -------------------------------------------------------------------------------------

Special details {#specialdetails}
===============

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å^2^) {#tablewrapcoords}
==================================================================================================

  ------ -------------- -------------- -------------- -------------------- --
         *x*            *y*            *z*            *U*~iso~\*/*U*~eq~   
  Ru1    0.67345 (2)    0.51144 (2)    0.37644 (2)    0.01639 (5)          
  Cl1    0.54447 (4)    0.65278 (5)    0.33000 (2)    0.02026 (11)         
  Cl2    0.77049 (4)    0.72523 (6)    0.39465 (2)    0.02641 (13)         
  N1     0.78992 (14)   0.3807 (2)     0.40882 (7)    0.0224 (4)           
  N2     0.72321 (14)   0.47141 (18)   0.31136 (7)    0.0169 (3)           
  N3     0.61032 (14)   0.31637 (19)   0.35845 (7)    0.0195 (4)           
  S1     0.61157 (5)    0.53018 (6)    0.44340 (2)    0.02421 (13)         
  O1     0.64939 (15)   0.4440 (2)     0.48897 (7)    0.0394 (5)           
  C14    0.4890 (2)     0.4893 (3)     0.42722 (10)   0.0321 (6)           
  H14A   0.459 (3)      0.515 (3)      0.4517 (13)    0.045 (10)\*         
  H14B   0.461 (2)      0.541 (3)      0.3971 (12)    0.038 (8)\*          
  H14C   0.485 (2)      0.388 (4)      0.4213 (11)    0.042 (9)\*          
  C15    0.6052 (2)     0.7116 (3)     0.46376 (11)   0.0346 (6)           
  H15A   0.571 (2)      0.713 (3)      0.4902 (11)    0.037 (8)\*          
  H15B   0.673 (3)      0.748 (4)      0.4742 (12)    0.063 (11)\*         
  H15C   0.576 (2)      0.775 (3)      0.4363 (10)    0.033 (8)\*          
  C1     0.8474 (2)     0.4251 (3)     0.45892 (9)    0.0308 (6)           
  H1A    0.8987 (18)    0.356 (3)      0.4712 (9)     0.018 (6)\*          
  H1B    0.873 (2)      0.523 (3)      0.4570 (11)    0.033 (8)\*          
  H1C    0.805 (2)      0.427 (3)      0.4826 (10)    0.028 (7)\*          
  C2     0.85411 (17)   0.3835 (3)     0.37313 (8)    0.0235 (5)           
  H2A    0.8994 (19)    0.303 (3)      0.3795 (9)     0.027 (7)\*          
  H2B    0.891 (2)      0.477 (3)      0.3815 (11)    0.030 (8)\*          
  C3     0.80268 (16)   0.3934 (2)     0.31945 (8)    0.0181 (4)           
  C4     0.83608 (18)   0.3340 (2)     0.28026 (9)    0.0221 (5)           
  H4     0.892 (2)      0.283 (3)      0.2870 (9)     0.025 (7)\*          
  C5     0.78772 (18)   0.3565 (2)     0.23159 (9)    0.0230 (5)           
  H5     0.8051 (18)    0.312 (3)      0.2059 (9)     0.022 (7)\*          
  C6     0.70671 (17)   0.4370 (3)     0.22333 (8)    0.0220 (5)           
  H6     0.6718 (19)    0.455 (3)      0.1914 (10)    0.024 (7)\*          
  C7     0.67585 (17)   0.4919 (2)     0.26393 (8)    0.0189 (4)           
  H7     0.617 (2)      0.545 (3)      0.2603 (10)    0.027 (7)\*          
  C8     0.7522 (2)     0.2349 (3)     0.41426 (10)   0.0293 (6)           
  H8A    0.736 (2)      0.230 (3)      0.4470 (11)    0.041 (9)\*          
  H8B    0.795 (2)      0.167 (3)      0.4131 (10)    0.027 (7)\*          
  C9     0.66441 (17)   0.2018 (2)     0.37632 (8)    0.0231 (5)           
  C10    0.6356 (2)     0.0633 (3)     0.36206 (11)   0.0315 (6)           
  H10    0.674 (2)      −0.012 (3)     0.3745 (10)    0.028 (8)\*          
  C11    0.5508 (2)     0.0411 (3)     0.33028 (12)   0.0355 (7)           
  H11    0.532 (2)      −0.043 (4)     0.3154 (12)    0.046 (9)\*          
  C12    0.4947 (2)     0.1582 (3)     0.31229 (11)   0.0318 (6)           
  H12    0.4356 (19)    0.140 (3)      0.2891 (10)    0.024 (7)\*          
  C13    0.52796 (18)   0.2934 (3)     0.32657 (9)    0.0240 (5)           
  H13    0.499 (2)      0.370 (3)      0.3156 (10)    0.029 (7)\*          
  ------ -------------- -------------- -------------- -------------------- --

Atomic displacement parameters (Å^2^) {#tablewrapadps}
=====================================

  ----- -------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^        *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  Ru1   0.01879 (10)   0.01715 (8)   0.01358 (7)   0.00499 (7)    0.00432 (6)    0.00194 (6)
  Cl1   0.0204 (3)     0.0194 (2)    0.0211 (2)    0.0071 (2)     0.0046 (2)     0.00371 (18)
  Cl2   0.0289 (3)     0.0227 (3)    0.0249 (3)    −0.0001 (2)    0.0002 (2)     −0.0007 (2)
  N1    0.0228 (11)    0.0253 (9)    0.0193 (8)    0.0090 (8)     0.0051 (7)     0.0030 (7)
  N2    0.0187 (9)     0.0165 (8)    0.0160 (8)    0.0026 (7)     0.0049 (7)     0.0007 (6)
  N3    0.0237 (10)    0.0179 (8)    0.0193 (8)    0.0050 (7)     0.0099 (7)     0.0034 (7)
  S1    0.0300 (3)     0.0280 (3)    0.0163 (2)    0.0123 (2)     0.0088 (2)     0.0041 (2)
  O1    0.0504 (13)    0.0511 (12)   0.0208 (8)    0.0271 (10)    0.0167 (8)     0.0156 (8)
  C14   0.0352 (16)    0.0393 (15)   0.0273 (12)   0.0084 (12)    0.0185 (11)    0.0049 (11)
  C15   0.0433 (18)    0.0339 (14)   0.0287 (13)   0.0102 (13)    0.0123 (13)    −0.0069 (11)
  C1    0.0302 (15)    0.0411 (15)   0.0178 (11)   0.0101 (12)    −0.0017 (10)   0.0010 (10)
  C2    0.0172 (12)    0.0316 (12)   0.0218 (10)   0.0084 (10)    0.0044 (9)     0.0020 (9)
  C3    0.0181 (11)    0.0184 (9)    0.0179 (9)    0.0012 (8)     0.0038 (8)     0.0018 (7)
  C4    0.0199 (12)    0.0243 (11)   0.0231 (10)   0.0044 (9)     0.0070 (9)     −0.0015 (8)
  C5    0.0240 (13)    0.0254 (11)   0.0217 (10)   0.0001 (9)     0.0093 (9)     −0.0050 (9)
  C6    0.0228 (12)    0.0259 (11)   0.0174 (10)   0.0012 (9)     0.0047 (9)     0.0010 (8)
  C7    0.0193 (11)    0.0217 (10)   0.0156 (9)    0.0013 (9)     0.0038 (8)     0.0004 (8)
  C8    0.0311 (15)    0.0254 (11)   0.0316 (13)   0.0110 (11)    0.0073 (11)    0.0113 (10)
  C9    0.0269 (13)    0.0197 (10)   0.0251 (11)   0.0058 (9)     0.0113 (9)     0.0058 (8)
  C10   0.0382 (16)    0.0195 (11)   0.0423 (15)   0.0079 (11)    0.0211 (13)    0.0063 (10)
  C11   0.0410 (17)    0.0200 (11)   0.0512 (17)   −0.0061 (11)   0.0224 (14)    −0.0047 (11)
  C12   0.0298 (15)    0.0251 (12)   0.0414 (15)   −0.0065 (11)   0.0101 (12)    −0.0044 (10)
  C13   0.0236 (13)    0.0223 (11)   0.0276 (11)   0.0025 (9)     0.0087 (10)    0.0021 (9)
  ----- -------------- ------------- ------------- -------------- -------------- --------------

Geometric parameters (Å, º) {#tablewrapgeomlong}
===========================

  ------------------- ------------- ------------------- -------------
  Ru1---N3            2.0515 (19)   C1---H1C            0.99 (3)
  Ru1---N2            2.0989 (18)   C2---C3             1.497 (3)
  Ru1---N1            2.1224 (19)   C2---H2A            0.99 (3)
  Ru1---S1            2.2207 (6)    C2---H2B            1.02 (3)
  Ru1---Cl1           2.4187 (5)    C3---C4             1.387 (3)
  Ru1---Cl2           2.4352 (6)    C4---C5             1.378 (3)
  N1---C8             1.489 (3)     C4---H4             0.93 (3)
  N1---C2             1.495 (3)     C5---C6             1.378 (3)
  N1---C1             1.499 (3)     C5---H5             0.90 (2)
  N2---C7             1.342 (3)     C6---C7             1.385 (3)
  N2---C3             1.347 (3)     C6---H6             0.92 (3)
  N3---C13            1.339 (3)     C7---H7             0.97 (3)
  N3---C9             1.355 (3)     C8---C9             1.493 (4)
  S1---O1             1.4838 (18)   C8---H8A            0.98 (3)
  S1---C14            1.788 (3)     C8---H8B            0.89 (3)
  S1---C15            1.791 (3)     C9---C10            1.389 (3)
  C14---H14A          0.91 (4)      C10---C11           1.364 (4)
  C14---H14B          0.96 (3)      C10---H10           0.92 (3)
  C14---H14C          0.96 (3)      C11---C12           1.390 (4)
  C15---H15A          0.97 (3)      C11---H11           0.90 (3)
  C15---H15B          1.03 (4)      C12---C13           1.378 (3)
  C15---H15C          0.97 (3)      C12---H12           0.97 (3)
  C1---H1A            0.99 (3)      C13---H13           0.85 (3)
  C1---H1B            0.99 (3)                          
                                                        
  N3---Ru1---N2       81.96 (7)     H1A---C1---H1B      110 (2)
  N3---Ru1---N1       82.34 (8)     N1---C1---H1C       107.1 (17)
  N2---Ru1---N1       81.70 (7)     H1A---C1---H1C      109 (2)
  N3---Ru1---S1       91.40 (5)     H1B---C1---H1C      109 (2)
  N2---Ru1---S1       173.35 (5)    N1---C2---C3        112.92 (19)
  N1---Ru1---S1       97.82 (5)     N1---C2---H2A       111.3 (15)
  N3---Ru1---Cl1      95.80 (5)     C3---C2---H2A       113.0 (15)
  N2---Ru1---Cl1      91.57 (5)     N1---C2---H2B       104.0 (17)
  N1---Ru1---Cl1      173.20 (5)    C3---C2---H2B       107.0 (17)
  S1---Ru1---Cl1      88.75 (2)     H2A---C2---H2B      108 (2)
  N3---Ru1---Cl2      170.84 (6)    N2---C3---C4        121.8 (2)
  N2---Ru1---Cl2      91.40 (5)     N2---C3---C2        114.98 (19)
  N1---Ru1---Cl2      90.49 (6)     C4---C3---C2        123.2 (2)
  S1---Ru1---Cl2      95.24 (2)     C5---C4---C3        119.5 (2)
  Cl1---Ru1---Cl2     90.66 (2)     C5---C4---H4        120.7 (16)
  C8---N1---C2        112.4 (2)     C3---C4---H4        119.8 (16)
  C8---N1---C1        107.8 (2)     C6---C5---C4        118.7 (2)
  C2---N1---C1        106.6 (2)     C6---C5---H5        120.2 (17)
  C8---N1---Ru1       106.67 (15)   C4---C5---H5        120.8 (16)
  C2---N1---Ru1       106.15 (13)   C5---C6---C7        119.3 (2)
  C1---N1---Ru1       117.32 (15)   C5---C6---H6        122.0 (17)
  C7---N2---C3        118.54 (19)   C7---C6---H6        118.6 (17)
  C7---N2---Ru1       126.34 (16)   N2---C7---C6        122.2 (2)
  C3---N2---Ru1       113.84 (14)   N2---C7---H7        115.1 (16)
  C13---N3---C9       118.5 (2)     C6---C7---H7        122.7 (16)
  C13---N3---Ru1      126.20 (16)   N1---C8---C9        113.56 (19)
  C9---N3---Ru1       114.71 (16)   N1---C8---H8A       108.0 (18)
  O1---S1---C14       105.03 (13)   C9---C8---H8A       106.0 (18)
  O1---S1---C15       106.66 (13)   N1---C8---H8B       111.6 (18)
  C14---S1---C15      99.25 (15)    C9---C8---H8B       109.2 (18)
  O1---S1---Ru1       120.38 (8)    H8A---C8---H8B      108 (2)
  C14---S1---Ru1      110.28 (9)    N3---C9---C10       121.1 (2)
  C15---S1---Ru1      112.91 (11)   N3---C9---C8        115.5 (2)
  S1---C14---H14A     112 (2)       C10---C9---C8       123.2 (2)
  S1---C14---H14B     108.9 (19)    C11---C10---C9      119.8 (2)
  H14A---C14---H14B   108 (3)       C11---C10---H10     121.3 (18)
  S1---C14---H14C     105.6 (19)    C9---C10---H10      118.9 (18)
  H14A---C14---H14C   112 (3)       C10---C11---C12     119.3 (2)
  H14B---C14---H14C   111 (3)       C10---C11---H11     124 (2)
  S1---C15---H15A     108.2 (18)    C12---C11---H11     115 (2)
  S1---C15---H15B     107 (2)       C13---C12---C11     118.4 (3)
  H15A---C15---H15B   115 (3)       C13---C12---H12     123.9 (16)
  S1---C15---H15C     112.1 (17)    C11---C12---H12     117.6 (16)
  H15A---C15---H15C   111 (2)       N3---C13---C12      122.8 (2)
  H15B---C15---H15C   104 (3)       N3---C13---H13      113 (2)
  N1---C1---H1A       111.2 (14)    C12---C13---H13     124 (2)
  N1---C1---H1B       110.4 (18)                        
                                                        
  N1---C8---C9---N3   −28.0 (3)     N1---C2---C3---N2   34.3 (3)
  ------------------- ------------- ------------------- -------------

Hydrogen-bond geometry (Å, º) {#tablewraphbondslong}
=============================

  ---------------------- ---------- ---------- ----------- ---------------
  *D*---H···*A*          *D*---H    H···*A*    *D*···*A*   *D*---H···*A*
  C14---H14*A*···O1^i^   0.91 (4)   2.54 (4)   3.431 (3)   169 (3)
  C4---H4···Cl1^ii^      0.93 (3)   2.58 (3)   3.487 (2)   165 (2)
  C1---H1*C*···O1        0.99 (3)   2.32 (3)   3.182 (4)   145 (2)
  ---------------------- ---------- ---------- ----------- ---------------

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

###### Hydrogen-bond geometry (, )

  *D*H*A*          *D*H      H*A*      *D* *A*    *D*H*A*
  ---------------- --------- --------- ---------- ---------
  C14H14*A*O1^i^   0.91(4)   2.54(4)   3.431(3)   169(3)
  C4H4Cl1^ii^      0.93(3)   2.58(3)   3.487(2)   165(2)
  C1H1*C*O1        0.99(3)   2.32(3)   3.182(4)   145(2)

Symmetry codes: (i) ; (ii) .
