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

For background on the chemistry of cobaloximes, see: Schrayzer (1968[@bb9]); Zangrando *et al.* (2003[@bb12]). For applications of cobaloximes in proton reduction, see: Raza­vet *et al.* (2005[@bb8]). For related structures, see: Bhuyan *et al.* (2007[@bb2]); Dutta *et al.* (2009[@bb4]); Mandal & Gupta (2005[@bb6], 2007[@bb7]); William *et al.* (1973[@bb11]). For NMR research on O---H⋯O bridges, see: Bakac & Espenson (1984[@bb1]). For deprotonation of O---H⋯O bridges by BF~3~·Et~2~O, see: Magnuson & Weber (1974[@bb5]).

Experimental {#sec2}
============

 {#sec2.1}

### Crystal data {#sec2.1.1}

\[Co(C~4~H~7~N~2~O~2~)~2~Cl(C~8~H~9~NO~2~)\]·CHCl~3~*M* *~r~* = 595.14Orthorhombic,*a* = 10.053 (3) Å*b* = 22.357 (7) Å*c* = 23.099 (8) Å*V* = 5192 (3) Å^3^*Z* = 8Mo *K*α radiationμ = 1.11 mm^−1^*T* = 293 K0.29 × 0.14 × 0.06 mm

### Data collection {#sec2.1.2}

Bruker APEXII area-detector diffractometerAbsorption correction: multi-scan (*SADABS*; Bruker, 2007[@bb3]) *T* ~min~ = 0.829, *T* ~max~ = 0.93524393 measured reflections4558 independent reflections3483 reflections with *I* \> 2σ(*I*)*R* ~int~ = 0.039

### Refinement {#sec2.1.3}

*R*\[*F* ^2^ \> 2σ(*F* ^2^)\] = 0.051*wR*(*F* ^2^) = 0.158*S* = 1.084558 reflections310 parametersH atoms treated by a mixture of independent and constrained refinementΔρ~max~ = 1.25 e Å^−3^Δρ~min~ = −0.78 e Å^−3^

 {#d5e555}

Data collection: *APEX2* (Bruker, 2007[@bb3]); cell refinement: *SAINT-Plus* (Bruker, 2007[@bb3]); data reduction: *SAINT-Plus*; program(s) used to solve structure: *SHELXS97* (Sheldrick, 2008[@bb10]); program(s) used to refine structure: *SHELXL97* (Sheldrick, 2008[@bb10]); molecular graphics: *SHELXTL* (Sheldrick, 2008[@bb10]); software used to prepare material for publication: *SHELXL97*.

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

Crystal structure: contains datablock(s) I, global. DOI: [10.1107/S1600536812002449/zl2444sup1.cif](http://dx.doi.org/10.1107/S1600536812002449/zl2444sup1.cif)

Structure factors: contains datablock(s) I. DOI: [10.1107/S1600536812002449/zl2444Isup2.hkl](http://dx.doi.org/10.1107/S1600536812002449/zl2444Isup2.hkl)

Additional supplementary materials: [crystallographic information](http://scripts.iucr.org/cgi-bin/sendsupfiles?zl2444&file=zl2444sup0.html&mime=text/html); [3D view](http://scripts.iucr.org/cgi-bin/sendcif?zl2444sup1&Qmime=cif); [checkCIF report](http://scripts.iucr.org/cgi-bin/paper?zl2444&checkcif=yes)

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: [ZL2444](http://scripts.iucr.org/cgi-bin/sendsup?zl2444)).

We are grateful to the Chinese National Natural Science Foundation (grant No. 21101057), the Science Foundation of the Education Department of Henan Province (No. 2011B150006) and the Doctoral Fund of Henan University of Technology (No. 2009BS053).

Comment
=======

The cobaloximes have extensively been used to mimic the vitamin B~12~ coenzyme (Schrayzer, 1968). Recently they also are used to catalyze proton reduction as a functional model of hydrogenase (Razavet *et al.*, 2005). The title compound, \[Co(dmgH)~2~(4-(COOEt)C~5~H~4~N)Cl\], was prepared as previously described (William *et al.*, 1973). The cobalt atom is coordinated in a distorted-octahedral geometry by four nitrogen atoms of the pseudomacrocyclic \[(dmgH)~2~\]^2-^ ligand in the equatorial plane and by one chlorine atom and a nitrogen atom of ethyl isonicotinate, respectively, in mutually *trans* positions (N5---Co---Cl1 = 179.33° (10)). The cobalt atom which is linked to four nitrogen atoms belonging to the equatorial plane, displays an approximately octahedral coordination. The mean Co---N bond length is 1.898 Å (3). The mean O---O distance between neighboring dimethylglyoximato oxygen atoms is 2.491 Å (5). These ligands form strong O---H···O bridges with each other which is very common in cobaloxime derivatives. The presence of the O---H···O bridging moieties in cobaloxime derivatives ensures coplanarity of the two ligand molecules and promotes the stability of the cobaloxime molecule (Zangrando *et al.*, 2003). The existence of O---H···O bridging is supported by the NMR data and further substantiated by their chemical behavior with BF~3~.Et~2~O in readily forming an O---BF~2~---O system by deprotonation of the O---H···O bridge (Bakac & Espenson, 1984; Magnuson & Weber, 1974). The distance between O2 and H2 is 1.14 (6) Å indicating a strongly hydrogen bonded nearly symmetric O---H···O system (Bhuyan *et al.*, 2007; Dutta *et al.*, 2009; Mandal & Gupta, 2005, 2007). The Co atom is 0.0240 Å (15) out of the mean plane of the four nitrogen atoms. The plane of the four nitrogen atoms is practically planar.

Experimental {#experimental}
============

Co(dmgH)(dmgH~2~)Cl, (3.6 g, 0.01 mol) and ethyl isonicotinate (3.0 g, 0.02 mol) were added to chloroform (90 ml) (William *et al.*,1973). The suspension was stirred for 20 minutes. Then water (30 ml) was added to the flask and the mixture was vigorously stirred for 2 h. The aqueous layer was discarded and the chloroform layer filtered and extracted with water until the washings were nearly colorless. The solution was reduced in volume and the product precipitated by addition of ethanol (95%); yield 69%. Brown single crystals of \[Co(dmgH)~2~(4-(COOEt)C~5~H~4~N)Cl\] were grown from a CHCl~3~/ethyl acetate solution (v:v = 1:1). ^1^H NMR (400 MHz, CDCl~3~): δ 8.45 (d, 6.4 Hz, 2 H, *o*-H~py~), 7.75 (d, 6 Hz, 2 H, *m*-H~py~), 4.38 (q, 7.2 Hz, 2 H, CH~2~), 2.30 (s, 12 H, N=CCH~3~), 1.35 (t, 7.0 Hz, 3 H, CH~3~).

Refinement {#refinement}
==========

H1 and H2 were located in difference Fourier maps and their positions and displacement parameters were fully rerfined. All other hydrogen atoms were placed in calculated positions and refined as riding with C---H = 0.93 Å (CH) and 0.97 Å (CH~3~), and with *U*~iso~(H) = 1.5Ueq(C) for the methyl group and *U*~iso~(H) = 1.2U~eq~(C) for all others.

Figures
=======

![The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.](e-68-0m204-fig1){#Fap1}

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

  ------------------------------------------------------ ---------------------------------------
  \[Co(C~4~H~7~N~2~O~2~)~2~Cl(C~8~H~9~NO~2~)\]·CHCl~3~   *F*(000) = 2432
  *M~r~* = 595.14                                        *D*~x~ = 1.523 Mg m^−3^
  Orthorhombic, *Pbca*                                   Mo *K*α radiation, λ = 0.71073 Å
  Hall symbol: -P 2ac 2ab                                Cell parameters from 5509 reflections
  *a* = 10.053 (3) Å                                     θ = 2.4--24.8°
  *b* = 22.357 (7) Å                                     µ = 1.11 mm^−1^
  *c* = 23.099 (8) Å                                     *T* = 293 K
  *V* = 5192 (3) Å^3^                                    Needle, brown
  *Z* = 8                                                0.29 × 0.14 × 0.06 mm
  ------------------------------------------------------ ---------------------------------------

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

  ------------------------------------------------------------ --------------------------------------
  Bruker APEXII area-detector diffractometer                   4558 independent reflections
  Radiation source: fine-focus sealed tube                     3483 reflections with *I* \> 2σ(*I*)
  graphite                                                     *R*~int~ = 0.039
  phi and ω scans                                              θ~max~ = 25.0°, θ~min~ = 2.0°
  Absorption correction: multi-scan (*SADABS*; Bruker, 2007)   *h* = −11→9
  *T*~min~ = 0.829, *T*~max~ = 0.935                           *k* = −26→26
  24393 measured reflections                                   *l* = −27→24
  ------------------------------------------------------------ --------------------------------------

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

  ------------------------------------- -------------------------------------------------------------------------------------------------
  Refinement on *F*^2^                  Primary atom site location: structure-invariant direct methods
  Least-squares matrix: full            Secondary atom site location: difference Fourier map
  *R*\[*F*^2^ \> 2σ(*F*^2^)\] = 0.051   Hydrogen site location: inferred from neighbouring sites
  *wR*(*F*^2^) = 0.158                  H atoms treated by a mixture of independent and constrained refinement
  *S* = 1.08                            *w* = 1/\[σ^2^(*F*~o~^2^) + (0.0892*P*)^2^ + 4.4304*P*\] where *P* = (*F*~o~^2^ + 2*F*~c~^2^)/3
  4558 reflections                      (Δ/σ)~max~ = 0.001
  310 parameters                        Δρ~max~ = 1.25 e Å^−3^
  0 restraints                          Δρ~min~ = −0.78 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.
  Refinement. Refinement of *F*^2^ against ALL reflections. The weighted *R*-factor *wR* and goodness of fit *S* are based on *F*^2^, conventional *R*-factors *R* are based on *F*, with *F* set to zero for negative *F*^2^. The threshold expression of *F*^2^ \> σ(*F*^2^) is used only for calculating *R*-factors(gt) *etc*. and is not relevant to the choice of reflections for refinement. *R*-factors based on *F*^2^ are statistically about twice as large as those based on *F*, and *R*- factors based on ALL data will be even larger.
  -----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

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

  ------ ------------- --------------- -------------- -------------------- --
         *x*           *y*             *z*            *U*~iso~\*/*U*~eq~   
  Co1    0.23591 (5)   0.00646 (2)     0.63484 (2)    0.03477 (19)         
  Cl1    0.08443 (9)   0.07824 (5)     0.62035 (4)    0.0473 (3)           
  N2     0.2686 (3)    0.00560 (14)    0.55381 (14)   0.0387 (7)           
  N4     0.3608 (3)    0.06594 (13)    0.65679 (12)   0.0364 (7)           
  O2     0.3577 (3)    0.04186 (12)    0.52883 (11)   0.0489 (7)           
  N3     0.1977 (3)    0.00927 (14)    0.71495 (13)   0.0407 (7)           
  N5     0.3706 (3)    −0.05592 (13)   0.64728 (13)   0.0406 (7)           
  O4     0.4372 (3)    0.09421 (12)    0.61771 (11)   0.0473 (7)           
  O3     0.1032 (3)    −0.02516 (14)   0.73944 (11)   0.0558 (7)           
  C4     0.3647 (4)    0.07978 (16)    0.71110 (15)   0.0384 (8)           
  N1     0.1090 (3)    −0.05257 (15)   0.61321 (13)   0.0443 (8)           
  C2     0.2011 (4)    −0.03273 (18)   0.52384 (15)   0.0438 (9)           
  O1     0.0261 (3)    −0.07852 (15)   0.65120 (13)   0.0617 (9)           
  C3     0.2708 (3)    0.04442 (17)    0.74594 (16)   0.0406 (9)           
  C1     0.1055 (4)    −0.06658 (18)   0.55898 (16)   0.0478 (10)          
  C6     0.2193 (5)    −0.0395 (2)     0.45984 (18)   0.0661 (13)          
  H6A    0.3024        −0.0591         0.4522         0.099\*              
  H6B    0.2193        −0.0008         0.4420         0.099\*              
  H6C    0.1478        −0.0630         0.4443         0.099\*              
  C7     0.2605 (4)    0.0476 (2)      0.81032 (17)   0.0580 (12)          
  H7A    0.1723        0.0599          0.8210         0.087\*              
  H7B    0.3238        0.0760          0.8248         0.087\*              
  H7C    0.2787        0.0089          0.8266         0.087\*              
  C9     0.4808 (4)    −0.05867 (19)   0.61441 (18)   0.0514 (10)          
  H9A    0.4920        −0.0307         0.5850         0.062\*              
  C8     0.4506 (4)    0.12779 (18)    0.73592 (18)   0.0522 (10)          
  H8A    0.5049        0.1446          0.7059         0.078\*              
  H8B    0.5065        0.1111          0.7655         0.078\*              
  H8C    0.3955        0.1585          0.7524         0.078\*              
  C10    0.5774 (4)    −0.10112 (19)   0.6225 (2)     0.0571 (11)          
  H10A   0.6512        −0.1022         0.5982         0.069\*              
  C13    0.3583 (4)    −0.09637 (18)   0.68994 (17)   0.0518 (10)          
  H13A   0.2825        −0.0953         0.7130         0.062\*              
  C5     0.0100 (5)    −0.1112 (2)     0.5347 (2)     0.0683 (13)          
  H5A    −0.0506       −0.1237         0.5645         0.102\*              
  H5B    0.0582        −0.1452         0.5205         0.102\*              
  H5C    −0.0389       −0.0933         0.5035         0.102\*              
  C11    0.5646 (5)    −0.14251 (19)   0.66696 (19)   0.0548 (11)          
  C12    0.4530 (5)    −0.1392 (2)     0.70090 (19)   0.0601 (12)          
  H12A   0.4414        −0.1659         0.7313         0.072\*              
  O5     0.7541 (4)    −0.1941 (2)     0.6368 (2)     0.1054 (16)          
  O6     0.6596 (6)    −0.2213 (2)     0.7205 (2)     0.134 (2)            
  C14    0.6648 (6)    −0.1899 (2)     0.6788 (3)     0.0737 (15)          
  C15    0.8560 (7)    −0.2399 (3)     0.6427 (4)     0.130 (3)            
  H15A   0.8681        −0.2498         0.6833         0.156\*              
  H15B   0.9399        −0.2252         0.6277         0.156\*              
  C16    0.8152 (9)    −0.2930 (4)     0.6107 (3)     0.127 (3)            
  H16A   0.8815        −0.3236         0.6149         0.191\*              
  H16B   0.8053        −0.2831         0.5705         0.191\*              
  H16C   0.7318        −0.3072         0.6256         0.191\*              
  Cl2    0.3288 (3)    0.21423 (11)    0.52934 (9)    0.1438 (9)           
  Cl3    0.2763 (2)    0.24725 (11)    0.64763 (12)   0.1451 (11)          
  Cl4    0.0658 (2)    0.24578 (13)    0.56700 (13)   0.1782 (13)          
  C17    0.2161 (6)    0.2156 (3)      0.5858 (2)     0.0785 (15)          
  H17A   0.1983        0.1736          0.5954         0.094\*              
  H2     0.406 (6)     0.064 (3)       0.568 (3)      0.105 (19)\*         
  H1     0.053 (6)     −0.060 (3)      0.683 (3)      0.10 (2)\*           
  ------ ------------- --------------- -------------- -------------------- --

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

  ----- ------------- ------------- ------------- -------------- -------------- --------------
        *U*^11^       *U*^22^       *U*^33^       *U*^12^        *U*^13^        *U*^23^
  Co1   0.0347 (3)    0.0443 (3)    0.0253 (3)    −0.0059 (2)    0.00124 (18)   0.00086 (19)
  Cl1   0.0387 (5)    0.0631 (6)    0.0401 (5)    0.0045 (4)     −0.0007 (4)    0.0016 (4)
  N2    0.0389 (17)   0.0465 (18)   0.0306 (17)   −0.0038 (14)   0.0041 (12)    0.0030 (13)
  N4    0.0354 (16)   0.0430 (16)   0.0308 (16)   −0.0006 (13)   −0.0008 (12)   0.0025 (13)
  O2    0.0527 (17)   0.0618 (17)   0.0321 (14)   −0.0127 (14)   0.0075 (12)    0.0021 (12)
  N3    0.0389 (17)   0.0536 (19)   0.0296 (16)   −0.0037 (14)   0.0033 (13)    0.0034 (13)
  N5    0.0424 (17)   0.0409 (17)   0.0384 (17)   −0.0040 (14)   −0.0010 (13)   0.0012 (13)
  O4    0.0460 (15)   0.0562 (16)   0.0398 (15)   −0.0164 (13)   0.0049 (11)    0.0074 (12)
  O3    0.0506 (17)   0.0802 (19)   0.0366 (15)   −0.0215 (15)   0.0116 (12)    0.0071 (14)
  C4    0.0384 (19)   0.0416 (19)   0.035 (2)     0.0047 (16)    −0.0036 (15)   0.0002 (15)
  N1    0.0430 (18)   0.0542 (19)   0.0358 (18)   −0.0111 (15)   −0.0005 (13)   0.0029 (14)
  C2    0.052 (2)     0.051 (2)     0.0293 (18)   −0.0015 (18)   −0.0021 (17)   −0.0057 (17)
  O1    0.065 (2)     0.078 (2)     0.0422 (17)   −0.0358 (17)   0.0040 (14)    0.0046 (16)
  C3    0.037 (2)     0.056 (2)     0.0287 (18)   0.0056 (17)    −0.0011 (15)   −0.0013 (17)
  C1    0.052 (2)     0.055 (2)     0.037 (2)     −0.0067 (19)   −0.0063 (17)   −0.0052 (18)
  C6    0.075 (3)     0.090 (4)     0.033 (2)     −0.014 (3)     0.003 (2)      −0.013 (2)
  C7    0.057 (3)     0.086 (3)     0.031 (2)     −0.006 (2)     0.0015 (17)    −0.005 (2)
  C9    0.047 (2)     0.051 (2)     0.056 (3)     0.0002 (19)    0.0069 (19)    0.0105 (19)
  C8    0.056 (2)     0.056 (2)     0.044 (2)     −0.007 (2)     −0.0107 (19)   −0.0058 (18)
  C10   0.049 (2)     0.054 (2)     0.068 (3)     0.004 (2)      0.004 (2)      0.002 (2)
  C13   0.059 (3)     0.054 (2)     0.042 (2)     −0.001 (2)     0.0035 (18)    0.0085 (19)
  C5    0.081 (3)     0.070 (3)     0.053 (3)     −0.029 (3)     −0.013 (2)     −0.007 (2)
  C11   0.061 (3)     0.048 (2)     0.055 (3)     0.003 (2)      −0.015 (2)     −0.002 (2)
  C12   0.080 (3)     0.052 (2)     0.048 (3)     0.001 (2)      −0.006 (2)     0.012 (2)
  O5    0.074 (3)     0.078 (3)     0.164 (5)     0.031 (2)      0.017 (3)      0.036 (3)
  O6    0.180 (5)     0.134 (4)     0.089 (3)     0.091 (4)      −0.008 (3)     0.028 (3)
  C14   0.084 (4)     0.057 (3)     0.081 (4)     0.016 (3)      −0.028 (3)     0.000 (3)
  C15   0.086 (5)     0.098 (5)     0.207 (9)     0.052 (4)      0.016 (5)      0.038 (6)
  C16   0.151 (8)     0.114 (6)     0.118 (6)     0.072 (6)      0.003 (5)      0.020 (5)
  Cl2   0.159 (2)     0.167 (2)     0.1055 (15)   0.0384 (17)    0.0411 (14)    0.0400 (13)
  Cl3   0.1212 (16)   0.178 (2)     0.1355 (19)   0.0474 (15)    −0.0562 (14)   −0.0717 (16)
  Cl4   0.1211 (17)   0.229 (3)     0.185 (3)     0.0840 (18)    −0.0778 (17)   −0.087 (2)
  C17   0.081 (4)     0.079 (4)     0.075 (4)     −0.007 (3)     −0.009 (3)     0.001 (3)
  ----- ------------- ------------- ------------- -------------- -------------- --------------

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

  ---------------- ------------- ------------------- ------------
  Co1---N3         1.891 (3)     C7---H7C            0.9600
  Co1---N4         1.898 (3)     C9---C10            1.370 (6)
  Co1---N2         1.901 (3)     C9---H9A            0.9300
  Co1---N1         1.902 (3)     C8---H8A            0.9600
  Co1---N5         1.965 (3)     C8---H8B            0.9600
  Co1---Cl1        2.2375 (12)   C8---H8C            0.9600
  N2---C2          1.294 (5)     C10---C11           1.389 (6)
  N2---O2          1.339 (4)     C10---H10A          0.9300
  N4---C4          1.293 (5)     C13---C12           1.374 (6)
  N4---O4          1.344 (4)     C13---H13A          0.9300
  O2---H2          1.14 (6)      C5---H5A            0.9600
  N3---C3          1.292 (5)     C5---H5B            0.9600
  N3---O3          1.347 (4)     C5---H5C            0.9600
  N5---C13         1.343 (5)     C11---C12           1.371 (6)
  N5---C9          1.345 (5)     C11---C14           1.487 (6)
  O4---H2          1.37 (6)      C12---H12A          0.9300
  C4---C3          1.471 (5)     O5---C14            1.325 (7)
  C4---C8          1.492 (5)     O5---C15            1.454 (7)
  N1---C1          1.292 (5)     O6---C14            1.194 (7)
  N1---O1          1.342 (4)     C15---C16           1.456 (11)
  C2---C1          1.468 (6)     C15---H15A          0.9700
  C2---C6          1.497 (5)     C15---H15B          0.9700
  O1---H1          0.89 (6)      C16---H16A          0.9600
  C3---C7          1.492 (5)     C16---H16B          0.9600
  C1---C5          1.493 (6)     C16---H16C          0.9600
  C6---H6A         0.9600        Cl2---C17           1.728 (6)
  C6---H6B         0.9600        Cl3---C17           1.705 (6)
  C6---H6C         0.9600        Cl4---C17           1.712 (6)
  C7---H7A         0.9600        C17---H17A          0.9800
  C7---H7B         0.9600                            
                                                     
  N3---Co1---N4    81.36 (13)    H7A---C7---H7B      109.5
  N3---Co1---N2    177.80 (13)   C3---C7---H7C       109.5
  N4---Co1---N2    98.96 (13)    H7A---C7---H7C      109.5
  N3---Co1---N1    98.27 (13)    H7B---C7---H7C      109.5
  N4---Co1---N1    179.30 (14)   N5---C9---C10       122.6 (4)
  N2---Co1---N1    81.39 (13)    N5---C9---H9A       118.7
  N3---Co1---N5    91.17 (13)    C10---C9---H9A      118.7
  N4---Co1---N5    90.15 (13)    C4---C8---H8A       109.5
  N2---Co1---N5    91.00 (13)    C4---C8---H8B       109.5
  N1---Co1---N5    90.45 (14)    H8A---C8---H8B      109.5
  N3---Co1---Cl1   89.10 (10)    C4---C8---H8C       109.5
  N4---Co1---Cl1   89.28 (9)     H8A---C8---H8C      109.5
  N2---Co1---Cl1   88.73 (10)    H8B---C8---H8C      109.5
  N1---Co1---Cl1   90.12 (11)    C9---C10---C11      119.8 (4)
  N5---Co1---Cl1   179.33 (10)   C9---C10---H10A     120.1
  C2---N2---O2     121.4 (3)     C11---C10---H10A    120.1
  C2---N2---Co1    116.3 (3)     N5---C13---C12      122.7 (4)
  O2---N2---Co1    122.3 (2)     N5---C13---H13A     118.6
  C4---N4---O4     121.5 (3)     C12---C13---H13A    118.6
  C4---N4---Co1    116.6 (2)     C1---C5---H5A       109.5
  O4---N4---Co1    121.9 (2)     C1---C5---H5B       109.5
  N2---O2---H2     102 (3)       H5A---C5---H5B      109.5
  C3---N3---O3     121.0 (3)     C1---C5---H5C       109.5
  C3---N3---Co1    116.5 (3)     H5A---C5---H5C      109.5
  O3---N3---Co1    122.4 (2)     H5B---C5---H5C      109.5
  C13---N5---C9    117.3 (4)     C12---C11---C10     117.6 (4)
  C13---N5---Co1   121.5 (3)     C12---C11---C14     119.2 (5)
  C9---N5---Co1    121.2 (3)     C10---C11---C14     123.2 (5)
  N4---O4---H2     102 (2)       C11---C12---C13     120.0 (4)
  N4---C4---C3     112.5 (3)     C11---C12---H12A    120.0
  N4---C4---C8     124.3 (3)     C13---C12---H12A    120.0
  C3---C4---C8     123.2 (3)     C14---O5---C15      117.3 (5)
  C1---N1---O1     120.8 (3)     O6---C14---O5       125.3 (5)
  C1---N1---Co1    116.2 (3)     O6---C14---C11      122.5 (6)
  O1---N1---Co1    123.0 (2)     O5---C14---C11      112.1 (5)
  N2---C2---C1     112.9 (3)     O5---C15---C16      109.1 (7)
  N2---C2---C6     122.1 (4)     O5---C15---H15A     109.9
  C1---C2---C6     125.0 (4)     C16---C15---H15A    109.9
  N1---O1---H1     99 (4)        O5---C15---H15B     109.9
  N3---C3---C4     112.9 (3)     C16---C15---H15B    109.9
  N3---C3---C7     122.8 (4)     H15A---C15---H15B   108.3
  C4---C3---C7     124.3 (3)     C15---C16---H16A    109.5
  N1---C1---C2     113.1 (3)     C15---C16---H16B    109.5
  N1---C1---C5     122.9 (4)     H16A---C16---H16B   109.5
  C2---C1---C5     123.9 (4)     C15---C16---H16C    109.5
  C2---C6---H6A    109.5         H16A---C16---H16C   109.5
  C2---C6---H6B    109.5         H16B---C16---H16C   109.5
  H6A---C6---H6B   109.5         Cl3---C17---Cl4     111.2 (3)
  C2---C6---H6C    109.5         Cl3---C17---Cl2     114.0 (3)
  H6A---C6---H6C   109.5         Cl4---C17---Cl2     113.2 (4)
  H6B---C6---H6C   109.5         Cl3---C17---H17A    105.9
  C3---C7---H7A    109.5         Cl4---C17---H17A    105.9
  C3---C7---H7B    109.5         Cl2---C17---H17A    105.9
  ---------------- ------------- ------------------- ------------

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

  ------------------- ---------- ---------- ----------- ---------------
  *D*---H···*A*       *D*---H    H···*A*    *D*···*A*   *D*---H···*A*
  O2---H2···O4        1.14 (6)   1.37 (6)   2.495 (4)   168 (5)
  O2---H2···N4        1.14 (6)   2.10 (6)   3.004 (4)   133 (4)
  O1---H1···O3        0.89 (6)   1.60 (6)   2.486 (4)   177 (6)
  O1---H1···N3        0.89 (6)   2.25 (6)   3.000 (4)   142 (5)
  C17---H17A···Cl1    0.98       2.49       3.437 (6)   163
  C6---H6C···Cl1^i^   0.96       2.79       3.675 (5)   153
  ------------------- ---------- ---------- ----------- ---------------

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

###### Hydrogen-bond geometry (Å, °)

  *D*---H⋯*A*         *D*---H    H⋯*A*      *D*⋯*A*     *D*---H⋯*A*
  ------------------- ---------- ---------- ----------- -------------
  O2---H2⋯O4          1.14 (6)   1.37 (6)   2.495 (4)   168 (5)
  O2---H2⋯N4          1.14 (6)   2.10 (6)   3.004 (4)   133 (4)
  O1---H1⋯O3          0.89 (6)   1.60 (6)   2.486 (4)   177 (6)
  O1---H1⋯N3          0.89 (6)   2.25 (6)   3.000 (4)   142 (5)
  C17---H17*A*⋯Cl1    0.98       2.49       3.437 (6)   163
  C6---H6*C*⋯Cl1^i^   0.96       2.79       3.675 (5)   153

Symmetry code: (i) .
