Bis[1-benzyl-2-(1,3-thia-zol-4-yl)-1H-benzimidazole-κ(2) N (2),N (3)]dichloridocobalt(II).

In the title compound, [CoCl2(C17H13N3S)2], the Co(II) atom exhibits a distorted octa-hedral coordination geometry involving two chloride ligands, one of which is split over two positions [refined site-occupancy ratio = 0.847 (18):0.153 (18)], and four N-atom donors from two 1-benzyl-2-(1,3-thia-zol-4-yl)-1H-benzimidazole ligands. The two chelate rings including the Co(II) atom are essentially planar, the maximum deviations from the mean planes being 0.080 (2) and 0.046 (2) Å; the dihedral angle between them is 74.1 (1)°. In both ligands, the thia-zole and benzimidazole rings are nearly coplanar, as indicated by the dihedral angles between their planes of 1.16 (8) and 6.29 (7)°. Each pendant benzene ring is almost perpendicular to the benzimidazole mol-ecule to which it is attached; the dihedral angles between their planes are 75.94 (9) and 75.55 (10)°. The crystal structure is stabilized by non-classical C-H⋯Cl hydrogen bonding forming a three-dimensional network.

Related literature

For background of the biochemical properties of thia­bendazole [2-(4′-thia­zol­yl)benzimidazole], see: Devereux et al. (2007 ▶); Kowala et al. (1971 ▶); Yan-Jua & Guang-Ganga (2009 ▶).

Experimental

Crystal data

[CoCl2(C17H13N3S)2]

M = 712.56

Triclinic,

a = 10.1311 (3) Å

b = 11.9582 (4) Å

c = 14.2633 (5) Å

α = 76.033 (3)°

β = 75.536 (3)°

γ = 69.707 (3)°

V = 1546.43 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.90 mm−1

T = 193 K

0.40 × 0.40 × 0.20 mm

Data collection

Bruker Kappa APEXII Quazar area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.682, T max = 0.840

11578 measured reflections

6284 independent reflections

5601 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.080

S = 1.05

6284 reflections

417 parameters

H-atom parameters constrained

Δρmax = 0.95 e Å−3

Δρmin = −0.68 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048751/bt6860sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048751/bt6860Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CoCl2(C17H13N3S)2]	Z = 2
Mr = 712.56	F(000) = 730
Triclinic, P1	Dx = 1.530 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1311 (3) Å	Cell parameters from 6245 reflections
b = 11.9582 (4) Å	θ = 5.1–26.4°
c = 14.2633 (5) Å	µ = 0.90 mm−1
α = 76.033 (3)°	T = 193 K
β = 75.536 (3)°	Block, pink
γ = 69.707 (3)°	0.40 × 0.40 × 0.20 mm
V = 1546.43 (9) Å3

Bruker Kappa APEXII Quazar area-detector diffractometer	6284 independent reflections
Radiation source: microfocus sealed tube	5601 reflections with I > 2σ(I)
Multilayer optics monochromator	Rint = 0.011
φ and ω scans	θmax = 26.4°, θmin = 5.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→11
Tmin = 0.682, Tmax = 0.840	k = −14→14
11578 measured reflections	l = −17→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H-atom parameters constrained
wR(F2) = 0.080	w = 1/[σ2(Fo2) + (0.0362P)2 + 1.3427P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
6284 reflections	Δρmax = 0.95 e Å−3
417 parameters	Δρmin = −0.68 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0040 (5)

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 F2 against all reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on all data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.6603 (2)	0.37010 (19)	0.43804 (14)	0.0281 (4)
H1	0.6306	0.4540	0.4409	0.034*
C2	0.7805 (2)	0.1569 (2)	0.44040 (15)	0.0327 (4)
H2	0.8419	0.0759	0.4434	0.039*
C3	0.64845 (19)	0.19650 (17)	0.41692 (13)	0.0223 (4)
C4	0.56253 (19)	0.13517 (16)	0.39322 (13)	0.0214 (4)
C5	0.3835 (2)	0.11633 (17)	0.35002 (13)	0.0236 (4)
C6	0.2527 (2)	0.13165 (19)	0.32592 (14)	0.0289 (4)
H6	0.1811	0.2082	0.3214	0.035*
C7	0.2314 (3)	0.0305 (2)	0.30877 (15)	0.0366 (5)
H7	0.1435	0.0381	0.2918	0.044*
C8	0.3360 (3)	−0.0824 (2)	0.31586 (16)	0.0388 (5)
H8	0.3176	−0.1493	0.3027	0.047*
C9	0.4642 (3)	−0.09957 (19)	0.34126 (15)	0.0346 (5)
H9	0.5349	−0.1765	0.3467	0.041*
C10	0.4850 (2)	0.00220 (17)	0.35870 (13)	0.0260 (4)
C11	0.7263 (2)	−0.08140 (17)	0.40841 (15)	0.0301 (4)
H11A	0.7035	−0.1588	0.4266	0.036*
H11B	0.7546	−0.0691	0.4659	0.036*
C12	0.8512 (2)	−0.09147 (16)	0.32447 (13)	0.0226 (4)
C13	0.9687 (2)	−0.19429 (17)	0.33241 (15)	0.0292 (4)
H13	0.9665	−0.2561	0.3884	0.035*
C14	1.0883 (2)	−0.20696 (19)	0.25942 (18)	0.0364 (5)
H14	1.1685	−0.2774	0.2651	0.044*
C15	1.0916 (2)	−0.11754 (19)	0.17831 (17)	0.0345 (5)
H15	1.1748	−0.1259	0.1285	0.041*
C16	0.9753 (2)	−0.01644 (18)	0.16905 (15)	0.0299 (4)
H16	0.9776	0.0445	0.1124	0.036*
C17	0.8548 (2)	−0.00304 (17)	0.24201 (14)	0.0256 (4)
H17	0.7744	0.0671	0.2355	0.031*
C18	0.0728 (2)	0.47264 (19)	0.31938 (17)	0.0328 (4)
H18	0.0335	0.4909	0.3837	0.039*
C19	0.1212 (2)	0.4361 (2)	0.15296 (17)	0.0370 (5)
H19	0.1224	0.4249	0.0890	0.044*
C20	0.2387 (2)	0.41930 (17)	0.18986 (15)	0.0258 (4)
C21	0.3907 (2)	0.38422 (16)	0.14785 (13)	0.0221 (4)
C22	0.61612 (19)	0.34029 (15)	0.14499 (13)	0.0211 (4)
C23	0.7512 (2)	0.31937 (16)	0.16493 (14)	0.0251 (4)
H23	0.7639	0.3202	0.2285	0.030*
C24	0.8657 (2)	0.29749 (18)	0.08846 (16)	0.0314 (4)
H24	0.9593	0.2821	0.0999	0.038*
C25	0.8473 (2)	0.29740 (19)	−0.00575 (16)	0.0349 (5)
H25	0.9291	0.2818	−0.0565	0.042*
C26	0.7144 (2)	0.31922 (18)	−0.02687 (15)	0.0308 (4)
H26	0.7020	0.3200	−0.0909	0.037*
C27	0.5995 (2)	0.34003 (16)	0.05055 (14)	0.0236 (4)
C28	0.3882 (2)	0.37895 (18)	−0.02866 (14)	0.0287 (4)
H28A	0.4548	0.3952	−0.0904	0.034*
H28B	0.3003	0.4492	−0.0273	0.034*
C29	0.3500 (2)	0.26816 (18)	−0.02967 (14)	0.0268 (4)
C30	0.3025 (3)	0.2664 (2)	−0.11220 (17)	0.0370 (5)
H30	0.2987	0.3317	−0.1658	0.044*
C31	0.2607 (3)	0.1699 (2)	−0.11673 (18)	0.0454 (6)
H31	0.2260	0.1699	−0.1728	0.055*
C32	0.2692 (3)	0.0738 (2)	−0.04062 (18)	0.0462 (6)
H32	0.2412	0.0071	−0.0442	0.055*
C33	0.3181 (3)	0.0742 (2)	0.04040 (19)	0.0531 (7)
H33	0.3247	0.0075	0.0929	0.064*
C34	0.3580 (3)	0.1720 (2)	0.04607 (17)	0.0441 (6)
H34	0.3912	0.1721	0.1027	0.053*
N1	0.58202 (16)	0.31923 (14)	0.41412 (11)	0.0224 (3)
N2	0.43504 (16)	0.19849 (13)	0.37231 (11)	0.0208 (3)
N3	0.59824 (17)	0.01613 (14)	0.38752 (12)	0.0253 (3)
N4	0.20969 (16)	0.43936 (14)	0.28531 (12)	0.0253 (3)
N5	0.48317 (16)	0.36795 (13)	0.20426 (11)	0.0208 (3)
N6	0.45439 (17)	0.36890 (14)	0.05423 (11)	0.0240 (3)
S1	0.82050 (6)	0.27380 (6)	0.46385 (4)	0.03746 (14)
S2	−0.02965 (6)	0.48051 (6)	0.23841 (5)	0.04537 (16)
Cl1	0.42867 (5)	0.58768 (4)	0.30588 (4)	0.03220 (12)
Cl2A	0.23855 (17)	0.40676 (12)	0.5152 (2)	0.0232 (5)	0.847 (18)
Cl2B	0.215 (2)	0.444 (4)	0.485 (2)	0.060 (6)	0.153 (18)
Co1	0.39016 (2)	0.39444 (2)	0.355093 (18)	0.02006 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0262 (9)	0.0369 (11)	0.0278 (10)	−0.0143 (8)	−0.0031 (8)	−0.0125 (8)
C2	0.0277 (10)	0.0361 (11)	0.0330 (11)	−0.0096 (8)	−0.0084 (8)	−0.0009 (9)
C3	0.0231 (9)	0.0251 (9)	0.0182 (8)	−0.0092 (7)	−0.0003 (7)	−0.0038 (7)
C4	0.0232 (9)	0.0223 (9)	0.0179 (8)	−0.0088 (7)	0.0017 (7)	−0.0049 (7)
C5	0.0313 (10)	0.0254 (9)	0.0181 (8)	−0.0162 (8)	0.0022 (7)	−0.0066 (7)
C6	0.0363 (11)	0.0312 (10)	0.0258 (9)	−0.0186 (9)	−0.0055 (8)	−0.0046 (8)
C7	0.0499 (13)	0.0449 (13)	0.0290 (10)	−0.0316 (11)	−0.0084 (9)	−0.0051 (9)
C8	0.0610 (15)	0.0334 (11)	0.0332 (11)	−0.0302 (11)	−0.0008 (10)	−0.0107 (9)
C9	0.0485 (13)	0.0253 (10)	0.0311 (10)	−0.0185 (9)	0.0061 (9)	−0.0100 (8)
C10	0.0327 (10)	0.0243 (9)	0.0213 (9)	−0.0140 (8)	0.0049 (7)	−0.0070 (7)
C11	0.0350 (11)	0.0207 (9)	0.0263 (10)	−0.0045 (8)	−0.0004 (8)	0.0001 (7)
C12	0.0255 (9)	0.0199 (9)	0.0240 (9)	−0.0066 (7)	−0.0052 (7)	−0.0066 (7)
C13	0.0319 (10)	0.0217 (9)	0.0356 (11)	−0.0061 (8)	−0.0129 (8)	−0.0041 (8)
C14	0.0229 (10)	0.0282 (10)	0.0582 (14)	−0.0025 (8)	−0.0070 (9)	−0.0161 (10)
C15	0.0291 (10)	0.0311 (11)	0.0464 (12)	−0.0140 (9)	0.0067 (9)	−0.0197 (9)
C16	0.0362 (11)	0.0258 (10)	0.0290 (10)	−0.0139 (8)	0.0027 (8)	−0.0092 (8)
C17	0.0286 (10)	0.0204 (9)	0.0255 (9)	−0.0053 (7)	−0.0027 (8)	−0.0051 (7)
C18	0.0215 (9)	0.0289 (10)	0.0474 (12)	−0.0078 (8)	−0.0027 (9)	−0.0087 (9)
C19	0.0327 (11)	0.0465 (13)	0.0368 (11)	−0.0206 (10)	−0.0141 (9)	0.0044 (10)
C20	0.0253 (9)	0.0224 (9)	0.0333 (10)	−0.0118 (7)	−0.0085 (8)	−0.0014 (8)
C21	0.0259 (9)	0.0180 (8)	0.0262 (9)	−0.0109 (7)	−0.0057 (7)	−0.0034 (7)
C22	0.0242 (9)	0.0151 (8)	0.0238 (9)	−0.0072 (7)	−0.0014 (7)	−0.0040 (7)
C23	0.0246 (9)	0.0215 (9)	0.0281 (9)	−0.0078 (7)	−0.0034 (7)	−0.0029 (7)
C24	0.0247 (10)	0.0253 (10)	0.0404 (11)	−0.0075 (8)	−0.0003 (8)	−0.0047 (8)
C25	0.0350 (11)	0.0267 (10)	0.0353 (11)	−0.0078 (8)	0.0089 (9)	−0.0097 (8)
C26	0.0409 (11)	0.0238 (9)	0.0269 (10)	−0.0107 (8)	0.0016 (8)	−0.0093 (8)
C27	0.0319 (10)	0.0150 (8)	0.0249 (9)	−0.0093 (7)	−0.0033 (7)	−0.0037 (7)
C28	0.0415 (11)	0.0254 (10)	0.0246 (9)	−0.0142 (8)	−0.0125 (8)	−0.0015 (7)
C29	0.0308 (10)	0.0275 (10)	0.0268 (9)	−0.0125 (8)	−0.0048 (8)	−0.0080 (8)
C30	0.0461 (13)	0.0391 (12)	0.0344 (11)	−0.0170 (10)	−0.0156 (10)	−0.0072 (9)
C31	0.0549 (15)	0.0564 (15)	0.0425 (13)	−0.0287 (12)	−0.0153 (11)	−0.0164 (11)
C32	0.0615 (16)	0.0519 (15)	0.0437 (13)	−0.0398 (13)	0.0016 (11)	−0.0201 (11)
C33	0.094 (2)	0.0456 (14)	0.0383 (13)	−0.0476 (15)	−0.0124 (13)	−0.0008 (11)
C34	0.0774 (18)	0.0400 (13)	0.0310 (11)	−0.0352 (13)	−0.0170 (11)	−0.0023 (9)
N1	0.0217 (7)	0.0267 (8)	0.0225 (7)	−0.0105 (6)	−0.0014 (6)	−0.0094 (6)
N2	0.0241 (8)	0.0209 (7)	0.0199 (7)	−0.0105 (6)	−0.0005 (6)	−0.0064 (6)
N3	0.0273 (8)	0.0198 (8)	0.0264 (8)	−0.0089 (6)	0.0030 (6)	−0.0050 (6)
N4	0.0198 (7)	0.0219 (8)	0.0358 (9)	−0.0076 (6)	−0.0030 (6)	−0.0085 (7)
N5	0.0223 (7)	0.0189 (7)	0.0233 (7)	−0.0089 (6)	−0.0036 (6)	−0.0042 (6)
N6	0.0313 (8)	0.0212 (7)	0.0246 (8)	−0.0126 (6)	−0.0072 (6)	−0.0042 (6)
S1	0.0308 (3)	0.0532 (3)	0.0371 (3)	−0.0197 (2)	−0.0136 (2)	−0.0056 (2)
S2	0.0221 (3)	0.0555 (4)	0.0574 (4)	−0.0146 (2)	−0.0140 (2)	0.0036 (3)
Cl1	0.0315 (2)	0.0200 (2)	0.0489 (3)	−0.00923 (18)	−0.0090 (2)	−0.0089 (2)
Cl2A	0.0228 (4)	0.0248 (8)	0.0240 (7)	−0.0103 (4)	0.0029 (3)	−0.0110 (4)
Cl2B	0.039 (4)	0.108 (13)	0.050 (8)	−0.038 (7)	0.011 (5)	−0.041 (10)
Co1	0.01664 (13)	0.02009 (13)	0.02660 (14)	−0.00703 (9)	−0.00087 (9)	−0.01077 (10)

C1—N1	1.298 (2)	C19—S2	1.710 (2)
C1—S1	1.701 (2)	C19—H19	0.9500
C1—H1	0.9500	C20—N4	1.381 (3)
C2—C3	1.354 (3)	C20—C21	1.456 (3)
C2—S1	1.708 (2)	C21—N5	1.318 (2)
C2—H2	0.9500	C21—N6	1.356 (2)
C3—N1	1.382 (2)	C22—N5	1.377 (2)
C3—C4	1.456 (3)	C22—C23	1.392 (3)
C4—N2	1.317 (2)	C22—C27	1.400 (3)
C4—N3	1.359 (2)	C23—C24	1.378 (3)
C5—N2	1.389 (2)	C23—H23	0.9500
C5—C6	1.392 (3)	C24—C25	1.402 (3)
C5—C10	1.394 (3)	C24—H24	0.9500
C6—C7	1.385 (3)	C25—C26	1.376 (3)
C6—H6	0.9500	C25—H25	0.9500
C7—C8	1.397 (3)	C26—C27	1.388 (3)
C7—H7	0.9500	C26—H26	0.9500
C8—C9	1.369 (3)	C27—N6	1.379 (2)
C8—H8	0.9500	C28—N6	1.460 (2)
C9—C10	1.392 (3)	C28—C29	1.508 (3)
C9—H9	0.9500	C28—H28A	0.9900
C10—N3	1.383 (3)	C28—H28B	0.9900
C11—N3	1.452 (2)	C29—C34	1.370 (3)
C11—C12	1.502 (3)	C29—C30	1.386 (3)
C11—H11A	0.9900	C30—C31	1.380 (3)
C11—H11B	0.9900	C30—H30	0.9500
C12—C17	1.381 (3)	C31—C32	1.372 (4)
C12—C13	1.388 (3)	C31—H31	0.9500
C13—C14	1.376 (3)	C32—C33	1.368 (3)
C13—H13	0.9500	C32—H32	0.9500
C14—C15	1.375 (3)	C33—C34	1.388 (3)
C14—H14	0.9500	C33—H33	0.9500
C15—C16	1.371 (3)	C34—H34	0.9500
C15—H15	0.9500	N1—Co1	2.1297 (15)
C16—C17	1.382 (3)	N2—Co1	2.1901 (15)
C16—H16	0.9500	N4—Co1	2.1429 (16)
C17—H17	0.9500	N5—Co1	2.1739 (15)
C18—N4	1.300 (3)	Cl1—Co1	2.3855 (5)
C18—S2	1.703 (2)	Cl2A—Cl2B	0.57 (5)
C18—H18	0.9500	Cl2A—Co1	2.4181 (19)
C19—C20	1.352 (3)	Cl2B—Co1	2.261 (9)
N1—C1—S1	114.29 (16)	C26—C25—H25	119.0
N1—C1—H1	122.9	C24—C25—H25	119.0
S1—C1—H1	122.9	C25—C26—C27	116.32 (19)
C3—C2—S1	110.12 (16)	C25—C26—H26	121.8
C3—C2—H2	124.9	C27—C26—H26	121.8
S1—C2—H2	124.9	N6—C27—C26	131.34 (18)
C2—C3—N1	114.08 (17)	N6—C27—C22	106.17 (16)
C2—C3—C4	132.60 (18)	C26—C27—C22	122.42 (18)
N1—C3—C4	113.32 (16)	N6—C28—C29	114.23 (16)
N2—C4—N3	113.06 (16)	N6—C28—H28A	108.7
N2—C4—C3	119.16 (16)	C29—C28—H28A	108.7
N3—C4—C3	127.76 (17)	N6—C28—H28B	108.7
N2—C5—C6	130.57 (18)	C29—C28—H28B	108.7
N2—C5—C10	109.28 (17)	H28A—C28—H28B	107.6
C6—C5—C10	120.10 (17)	C34—C29—C30	119.26 (19)
C7—C6—C5	117.1 (2)	C34—C29—C28	123.75 (18)
C7—C6—H6	121.4	C30—C29—C28	116.99 (18)
C5—C6—H6	121.4	C31—C30—C29	120.2 (2)
C6—C7—C8	121.7 (2)	C31—C30—H30	119.9
C6—C7—H7	119.1	C29—C30—H30	119.9
C8—C7—H7	119.1	C32—C31—C30	120.3 (2)
C9—C8—C7	121.93 (19)	C32—C31—H31	119.9
C9—C8—H8	119.0	C30—C31—H31	119.9
C7—C8—H8	119.0	C33—C32—C31	119.8 (2)
C8—C9—C10	116.2 (2)	C33—C32—H32	120.1
C8—C9—H9	121.9	C31—C32—H32	120.1
C10—C9—H9	121.9	C32—C33—C34	120.2 (2)
N3—C10—C9	131.1 (2)	C32—C33—H33	119.9
N3—C10—C5	105.95 (16)	C34—C33—H33	119.9
C9—C10—C5	122.9 (2)	C29—C34—C33	120.3 (2)
N3—C11—C12	114.20 (15)	C29—C34—H34	119.9
N3—C11—H11A	108.7	C33—C34—H34	119.9
C12—C11—H11A	108.7	C1—N1—C3	111.49 (16)
N3—C11—H11B	108.7	C1—N1—Co1	131.34 (14)
C12—C11—H11B	108.7	C3—N1—Co1	116.57 (12)
H11A—C11—H11B	107.6	C4—N2—C5	105.28 (15)
C17—C12—C13	119.35 (18)	C4—N2—Co1	113.82 (12)
C17—C12—C11	123.18 (17)	C5—N2—Co1	139.41 (13)
C13—C12—C11	117.45 (17)	C4—N3—C10	106.42 (16)
C14—C13—C12	120.21 (19)	C4—N3—C11	128.90 (17)
C14—C13—H13	119.9	C10—N3—C11	124.67 (16)
C12—C13—H13	119.9	C18—N4—C20	111.57 (17)
C15—C14—C13	119.97 (19)	C18—N4—Co1	131.45 (15)
C15—C14—H14	120.0	C20—N4—Co1	116.63 (12)
C13—C14—H14	120.0	C21—N5—C22	105.84 (15)
C16—C15—C14	120.30 (19)	C21—N5—Co1	115.38 (12)
C16—C15—H15	119.9	C22—N5—Co1	138.75 (12)
C14—C15—H15	119.9	C21—N6—C27	106.33 (15)
C15—C16—C17	120.08 (19)	C21—N6—C28	128.80 (17)
C15—C16—H16	120.0	C27—N6—C28	124.88 (16)
C17—C16—H16	120.0	C1—S1—C2	89.98 (10)
C12—C17—C16	120.09 (18)	C18—S2—C19	90.14 (10)
C12—C17—H17	120.0	Cl2B—Cl2A—Co1	67.3 (11)
C16—C17—H17	120.0	Cl2A—Cl2B—Co1	99 (2)
N4—C18—S2	114.02 (17)	N1—Co1—N4	169.37 (6)
N4—C18—H18	123.0	N1—Co1—N5	98.02 (6)
S2—C18—H18	123.0	N4—Co1—N5	75.45 (6)
C20—C19—S2	109.95 (17)	N1—Co1—N2	75.58 (6)
C20—C19—H19	125.0	N4—Co1—N2	94.82 (6)
S2—C19—H19	125.0	N5—Co1—N2	79.86 (5)
C19—C20—N4	114.31 (18)	N1—Co1—Cl2B	104.7 (9)
C19—C20—C21	132.2 (2)	N4—Co1—Cl2B	81.7 (8)
N4—C20—C21	113.53 (16)	N5—Co1—Cl2B	157.1 (8)
N5—C21—N6	112.85 (16)	N2—Co1—Cl2B	102.9 (11)
N5—C21—C20	118.58 (17)	N1—Co1—Cl1	91.26 (4)
N6—C21—C20	128.53 (17)	N4—Co1—Cl1	96.61 (4)
N5—C22—C23	130.57 (17)	N5—Co1—Cl1	86.27 (4)
N5—C22—C27	108.81 (16)	N2—Co1—Cl1	159.21 (4)
C23—C22—C27	120.57 (17)	Cl2B—Co1—Cl1	95.9 (9)
C24—C23—C22	117.13 (18)	N1—Co1—Cl2A	93.31 (8)
C24—C23—H23	121.4	N4—Co1—Cl2A	91.82 (8)
C22—C23—H23	121.4	N5—Co1—Cl2A	164.99 (7)
C23—C24—C25	121.7 (2)	N2—Co1—Cl2A	93.56 (5)
C23—C24—H24	119.2	Cl2B—Co1—Cl2A	13.4 (12)
C25—C24—H24	119.2	Cl1—Co1—Cl2A	103.35 (3)
C26—C25—C24	121.90 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···Cl2Ai	0.99	2.77	3.693 (2)	155
C14—H14···Cl1ii	0.95	2.69	3.584 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯Cl2A i	0.99	2.77	3.693 (2)	155
C14—H14⋯Cl1ii	0.95	2.69	3.584 (2)	157

Symmetry codes: (i) ; (ii) .