Dichloridobis(3,4,5-trimethyl-1H-pyrazole-κN)cobalt(II).

In the title compound, [Co(II)Cl(2)(C(6)H(10)N(2))(2)], a pair of 3,4,5-trimethyl-pyrazoles act as monodentate ligands. Two Cl(-) anions are also bonded directly to the Co(II) atom, which has a CoN(2)Cl(2) chromophore in a slightly distorted tetra-hedral geometry. The two mol-ecules in the asymmetric unit are related by an approximate twofold rotation roughly parallel to the a axis. The amino H atom in the pyrazole ring participates in weak N-H⋯Cl hydrogen bonds to form chains that propagate roughly parallel to the c axis.

Related literature

For a similar tetra­hedral complex with pyrazole, see: Zyryanova et al. (2005 ▶). For thermal decomposition studies, see: Petrovic et al. (1993 ▶). For a similar tetra­hedral complex with 3,5-dimethyl­pyrazole, see: Leovac et al. (2007 ▶). For potential catalytic applications, see: Li et al. (2009 ▶); Oki et al. (1995 ▶). For additional related complexes, see: Sheu et al. (1996 ▶); Lyubartseva & Parkin (2010 ▶).

Experimental

Crystal data

[CoCl2(C6H10N2)2]

M = 350.15

Orthorhombic,

a = 14.8880 (1) Å

b = 17.3980 (1) Å

c = 24.9220 (2) Å

V = 6455.33 (8) Å3

Z = 16

Mo Kα radiation

μ = 1.39 mm−1

T = 90 K

0.30 × 0.28 × 0.19 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.590, T max = 0.746

111609 measured reflections

7404 independent reflections

5822 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.15

7404 reflections

355 parameters

H-atom parameters constrained

Δρmax = 0.80 e Å−3

Δρmin = −0.60 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and local procedures.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003254X/ng5017sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003254X/ng5017Isup2.hkl

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

[CoCl2(C6H10N2)2]	F(000) = 2896
Mr = 350.15	Dx = 1.441 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 15242 reflections
a = 14.8880 (1) Å	θ = 1.0–27.5°
b = 17.3980 (1) Å	µ = 1.39 mm−1
c = 24.9220 (2) Å	T = 90 K
V = 6455.33 (8) Å3	Block, blue
Z = 16	0.30 × 0.28 × 0.19 mm

Nonius KappaCCD diffractometer	7404 independent reflections
Radiation source: fine-focus sealed tube	5822 reflections with I > 2σ(I)
graphite	Rint = 0.064
Detector resolution: 9.1 pixels mm-1	θmax = 27.5°, θmin = 1.6°
ω scans at fixed χ = 55°	h = −19→19
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −22→22
Tmin = 0.590, Tmax = 0.746	l = −32→32
111609 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.0507P)2 + 7.0674P] where P = (Fo2 + 2Fc2)/3
7404 reflections	(Δ/σ)max = 0.001
355 parameters	Δρmax = 0.80 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

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
Co1A	0.70074 (2)	0.11088 (2)	0.365286 (14)	0.01780 (10)
Cl1A	0.73843 (5)	0.00580 (4)	0.31744 (3)	0.02255 (15)
Cl2A	0.80296 (5)	0.16183 (4)	0.42223 (3)	0.02503 (15)
N1A	0.59573 (15)	0.09270 (13)	0.41394 (9)	0.0205 (5)
N2A	0.59238 (15)	0.12310 (13)	0.46421 (8)	0.0211 (5)
H2A	0.6375	0.1468	0.4799	0.025*
N3A	0.66803 (15)	0.18364 (13)	0.30568 (8)	0.0196 (5)
N4A	0.66770 (14)	0.16085 (12)	0.25323 (8)	0.0179 (4)
H4A	0.6812	0.1142	0.2423	0.021*
C1A	0.51360 (18)	0.06308 (14)	0.40500 (10)	0.0192 (5)
C2A	0.45852 (19)	0.07446 (15)	0.44974 (10)	0.0218 (6)
C3A	0.51108 (19)	0.11215 (15)	0.48690 (11)	0.0223 (6)
C4A	0.49183 (19)	0.02581 (17)	0.35250 (11)	0.0268 (6)
H4A1	0.4978	0.0636	0.3236	0.040*
H4A2	0.4301	0.0063	0.3534	0.040*
H4A3	0.5334	−0.0169	0.3462	0.040*
C5A	0.36239 (19)	0.05170 (19)	0.45728 (12)	0.0306 (7)
H5A1	0.3534	0.0335	0.4941	0.046*
H5A2	0.3472	0.0105	0.4320	0.046*
H5A3	0.3236	0.0962	0.4506	0.046*
C6A	0.4881 (2)	0.13878 (18)	0.54196 (11)	0.0290 (6)
H6A1	0.5432	0.1525	0.5612	0.044*
H6A2	0.4570	0.0975	0.5613	0.044*
H6A3	0.4488	0.1839	0.5397	0.044*
C7A	0.64302 (17)	0.25790 (15)	0.30523 (11)	0.0195 (5)
C8A	0.62787 (17)	0.28238 (15)	0.25262 (11)	0.0203 (5)
C9A	0.64395 (17)	0.21919 (15)	0.22035 (10)	0.0189 (5)
C10A	0.6328 (2)	0.30248 (16)	0.35591 (11)	0.0258 (6)
H10A	0.5689	0.3114	0.3629	0.039*
H10B	0.6638	0.3519	0.3524	0.039*
H10C	0.6591	0.2734	0.3857	0.039*
C11A	0.60097 (19)	0.36179 (15)	0.23513 (12)	0.0257 (6)
H11A	0.6074	0.3662	0.1961	0.039*
H11B	0.6397	0.3998	0.2527	0.039*
H11C	0.5383	0.3712	0.2451	0.039*
C12A	0.6347 (2)	0.20858 (17)	0.16140 (10)	0.0261 (6)
H12A	0.6667	0.1619	0.1504	0.039*
H12B	0.6603	0.2531	0.1428	0.039*
H12C	0.5710	0.2037	0.1521	0.039*
Co1B	0.31918 (2)	0.40924 (2)	0.373980 (14)	0.01860 (10)
Cl1B	0.27079 (5)	0.51575 (4)	0.33151 (3)	0.02458 (16)
Cl2B	0.22703 (5)	0.34966 (4)	0.43286 (3)	0.02729 (16)
N1B	0.42685 (15)	0.42502 (13)	0.42153 (9)	0.0206 (5)
N2B	0.43489 (16)	0.38675 (13)	0.46881 (8)	0.0217 (5)
H2B	0.3908	0.3616	0.4844	0.026*
N3B	0.34707 (15)	0.33970 (13)	0.31166 (8)	0.0194 (5)
N4B	0.34550 (15)	0.36468 (12)	0.25999 (8)	0.0192 (5)
H4B	0.3320	0.4119	0.2503	0.023*
C1B	0.50868 (18)	0.45440 (15)	0.41148 (10)	0.0203 (5)
C2B	0.56832 (18)	0.43508 (15)	0.45274 (11)	0.0211 (5)
C3B	0.51843 (18)	0.39196 (15)	0.48875 (10)	0.0211 (6)
C4B	0.52534 (19)	0.49953 (17)	0.36144 (11)	0.0259 (6)
H4B1	0.5535	0.4663	0.3345	0.039*
H4B2	0.5653	0.5428	0.3695	0.039*
H4B3	0.4682	0.5190	0.3475	0.039*
C5B	0.66573 (19)	0.45395 (18)	0.45800 (12)	0.0286 (6)
H5B1	0.6763	0.4799	0.4923	0.043*
H5B2	0.6838	0.4879	0.4285	0.043*
H5B3	0.7011	0.4065	0.4566	0.043*
C6B	0.5461 (2)	0.35618 (17)	0.54041 (11)	0.0283 (6)
H6B1	0.4926	0.3404	0.5605	0.042*
H6B2	0.5803	0.3935	0.5616	0.042*
H6B3	0.5837	0.3111	0.5332	0.042*
C7B	0.37141 (17)	0.26534 (15)	0.30912 (11)	0.0198 (5)
C8B	0.38400 (18)	0.24321 (15)	0.25563 (11)	0.0204 (5)
C9B	0.36707 (17)	0.30816 (15)	0.22547 (10)	0.0191 (5)
C10B	0.3832 (2)	0.21733 (17)	0.35834 (11)	0.0284 (6)
H10D	0.4472	0.2073	0.3641	0.043*
H10E	0.3513	0.1685	0.3538	0.043*
H10F	0.3587	0.2447	0.3894	0.043*
C11B	0.41032 (19)	0.16500 (15)	0.23556 (11)	0.0251 (6)
H11D	0.4018	0.1627	0.1966	0.038*
H11E	0.3728	0.1259	0.2528	0.038*
H11F	0.4736	0.1554	0.2441	0.038*
C12B	0.37356 (19)	0.32148 (16)	0.16644 (10)	0.0239 (6)
H12D	0.3412	0.3686	0.1571	0.036*
H12E	0.3470	0.2778	0.1473	0.036*
H12F	0.4368	0.3267	0.1562	0.036*

	U11	U22	U33	U12	U13	U23
Co1A	0.01982 (19)	0.01854 (19)	0.01504 (18)	0.00059 (14)	−0.00063 (13)	0.00002 (13)
Cl1A	0.0250 (3)	0.0212 (3)	0.0215 (3)	0.0030 (3)	−0.0011 (3)	−0.0038 (2)
Cl2A	0.0271 (4)	0.0282 (3)	0.0198 (3)	−0.0053 (3)	−0.0059 (3)	0.0020 (3)
N1A	0.0224 (12)	0.0221 (11)	0.0170 (11)	0.0012 (9)	−0.0023 (9)	−0.0016 (9)
N2A	0.0228 (12)	0.0264 (12)	0.0140 (11)	−0.0016 (9)	−0.0001 (9)	−0.0019 (9)
N3A	0.0226 (12)	0.0205 (11)	0.0158 (11)	0.0007 (9)	−0.0003 (9)	−0.0010 (9)
N4A	0.0189 (11)	0.0192 (11)	0.0156 (10)	0.0009 (9)	−0.0016 (8)	−0.0012 (8)
C1A	0.0212 (13)	0.0163 (12)	0.0202 (13)	0.0009 (10)	−0.0024 (10)	0.0017 (10)
C2A	0.0230 (14)	0.0222 (13)	0.0202 (13)	0.0014 (11)	−0.0001 (11)	0.0025 (11)
C3A	0.0248 (14)	0.0225 (13)	0.0197 (13)	0.0022 (11)	0.0027 (11)	0.0019 (10)
C4A	0.0224 (14)	0.0328 (16)	0.0254 (15)	0.0015 (12)	−0.0029 (12)	−0.0062 (12)
C5A	0.0255 (15)	0.0382 (17)	0.0280 (15)	−0.0046 (13)	0.0010 (12)	0.0020 (13)
C6A	0.0288 (16)	0.0378 (17)	0.0204 (14)	0.0002 (13)	0.0046 (12)	−0.0023 (12)
C7A	0.0177 (13)	0.0187 (13)	0.0222 (13)	−0.0005 (10)	0.0000 (10)	−0.0015 (10)
C8A	0.0166 (13)	0.0201 (13)	0.0241 (14)	−0.0002 (10)	−0.0010 (10)	0.0004 (11)
C9A	0.0163 (12)	0.0214 (13)	0.0191 (13)	−0.0008 (10)	−0.0023 (10)	0.0025 (10)
C10A	0.0291 (15)	0.0228 (14)	0.0255 (14)	0.0043 (12)	−0.0019 (12)	−0.0049 (11)
C11A	0.0256 (15)	0.0220 (14)	0.0295 (15)	0.0019 (11)	−0.0064 (12)	0.0038 (11)
C12A	0.0312 (16)	0.0290 (15)	0.0180 (13)	−0.0003 (12)	−0.0025 (11)	0.0044 (11)
Co1B	0.02032 (19)	0.01980 (19)	0.01568 (18)	0.00110 (14)	0.00118 (14)	−0.00009 (14)
Cl1B	0.0278 (4)	0.0231 (3)	0.0228 (3)	0.0049 (3)	0.0012 (3)	0.0036 (3)
Cl2B	0.0298 (4)	0.0324 (4)	0.0197 (3)	−0.0072 (3)	0.0068 (3)	−0.0024 (3)
N1B	0.0229 (12)	0.0228 (11)	0.0161 (11)	−0.0006 (9)	0.0005 (9)	0.0013 (9)
N2B	0.0250 (12)	0.0245 (12)	0.0155 (11)	0.0001 (9)	0.0014 (9)	0.0033 (9)
N3B	0.0211 (11)	0.0222 (11)	0.0150 (10)	0.0013 (9)	0.0015 (9)	0.0021 (9)
N4B	0.0225 (12)	0.0192 (11)	0.0158 (11)	0.0011 (9)	0.0014 (9)	0.0027 (8)
C1B	0.0222 (14)	0.0202 (13)	0.0186 (13)	0.0015 (11)	0.0012 (10)	−0.0012 (10)
C2B	0.0213 (14)	0.0213 (13)	0.0208 (13)	0.0031 (11)	−0.0003 (11)	−0.0021 (11)
C3B	0.0236 (14)	0.0219 (13)	0.0179 (13)	0.0036 (11)	−0.0004 (11)	−0.0035 (10)
C4B	0.0221 (14)	0.0305 (15)	0.0249 (15)	−0.0003 (12)	0.0014 (11)	0.0042 (12)
C5B	0.0257 (15)	0.0319 (16)	0.0282 (15)	−0.0009 (12)	−0.0024 (12)	0.0016 (12)
C6B	0.0307 (16)	0.0327 (16)	0.0216 (14)	0.0004 (13)	−0.0014 (12)	0.0023 (12)
C7B	0.0183 (13)	0.0182 (13)	0.0229 (14)	−0.0003 (10)	0.0005 (10)	−0.0006 (10)
C8B	0.0172 (13)	0.0216 (13)	0.0224 (13)	−0.0007 (10)	0.0013 (10)	−0.0017 (11)
C9B	0.0159 (13)	0.0216 (13)	0.0197 (13)	−0.0029 (10)	0.0017 (10)	−0.0039 (10)
C10B	0.0346 (17)	0.0256 (15)	0.0250 (15)	0.0044 (13)	0.0016 (12)	0.0044 (12)
C11B	0.0246 (15)	0.0208 (14)	0.0299 (15)	0.0027 (11)	0.0032 (12)	−0.0050 (11)
C12B	0.0289 (15)	0.0241 (14)	0.0188 (13)	−0.0027 (11)	0.0013 (11)	−0.0006 (11)

Co1A—N1A	2.004 (2)	Co1B—N3B	2.012 (2)
Co1A—N3A	2.012 (2)	Co1B—N1B	2.012 (2)
Co1A—Cl1A	2.2536 (7)	Co1B—Cl1B	2.2524 (7)
Co1A—Cl2A	2.2617 (7)	Co1B—Cl2B	2.2606 (7)
N1A—C1A	1.346 (3)	N1B—C1B	1.345 (3)
N1A—N2A	1.361 (3)	N1B—N2B	1.359 (3)
N2A—C3A	1.350 (3)	N2B—C3B	1.342 (4)
N2A—H2A	0.8800	N2B—H2B	0.8800
N3A—C7A	1.345 (3)	N3B—C7B	1.345 (3)
N3A—N4A	1.366 (3)	N3B—N4B	1.359 (3)
N4A—C9A	1.352 (3)	N4B—C9B	1.345 (3)
N4A—H4A	0.8800	N4B—H4B	0.8800
C1A—C2A	1.398 (4)	C1B—C2B	1.400 (4)
C1A—C4A	1.496 (4)	C1B—C4B	1.494 (4)
C2A—C3A	1.378 (4)	C2B—C3B	1.386 (4)
C2A—C5A	1.497 (4)	C2B—C5B	1.493 (4)
C3A—C6A	1.488 (4)	C3B—C6B	1.488 (4)
C4A—H4A1	0.9800	C4B—H4B1	0.9800
C4A—H4A2	0.9800	C4B—H4B2	0.9800
C4A—H4A3	0.9800	C4B—H4B3	0.9800
C5A—H5A1	0.9800	C5B—H5B1	0.9800
C5A—H5A2	0.9800	C5B—H5B2	0.9800
C5A—H5A3	0.9800	C5B—H5B3	0.9800
C6A—H6A1	0.9800	C6B—H6B1	0.9800
C6A—H6A2	0.9800	C6B—H6B2	0.9800
C6A—H6A3	0.9800	C6B—H6B3	0.9800
C7A—C8A	1.397 (4)	C7B—C8B	1.400 (4)
C7A—C10A	1.490 (4)	C7B—C10B	1.494 (4)
C8A—C9A	1.383 (4)	C8B—C9B	1.380 (4)
C8A—C11A	1.503 (4)	C8B—C11B	1.502 (4)
C9A—C12A	1.487 (4)	C9B—C12B	1.493 (4)
C10A—H10A	0.9800	C10B—H10D	0.9800
C10A—H10B	0.9800	C10B—H10E	0.9800
C10A—H10C	0.9800	C10B—H10F	0.9800
C11A—H11A	0.9800	C11B—H11D	0.9800
C11A—H11B	0.9800	C11B—H11E	0.9800
C11A—H11C	0.9800	C11B—H11F	0.9800
C12A—H12A	0.9800	C12B—H12D	0.9800
C12A—H12B	0.9800	C12B—H12E	0.9800
C12A—H12C	0.9800	C12B—H12F	0.9800
N1A—Co1A—N3A	110.94 (9)	N3B—Co1B—N1B	111.86 (9)
N1A—Co1A—Cl1A	112.73 (7)	N3B—Co1B—Cl1B	101.42 (6)
N3A—Co1A—Cl1A	100.38 (6)	N1B—Co1B—Cl1B	114.79 (7)
N1A—Co1A—Cl2A	101.96 (7)	N3B—Co1B—Cl2B	110.52 (7)
N3A—Co1A—Cl2A	112.31 (7)	N1B—Co1B—Cl2B	99.43 (7)
Cl1A—Co1A—Cl2A	118.84 (3)	Cl1B—Co1B—Cl2B	119.22 (3)
C1A—N1A—N2A	105.5 (2)	C1B—N1B—N2B	105.6 (2)
C1A—N1A—Co1A	132.03 (18)	C1B—N1B—Co1B	131.60 (18)
N2A—N1A—Co1A	121.63 (17)	N2B—N1B—Co1B	120.93 (17)
C3A—N2A—N1A	111.3 (2)	C3B—N2B—N1B	111.7 (2)
C3A—N2A—H2A	124.3	C3B—N2B—H2B	124.2
N1A—N2A—H2A	124.3	N1B—N2B—H2B	124.2
C7A—N3A—N4A	105.7 (2)	C7B—N3B—N4B	105.5 (2)
C7A—N3A—Co1A	132.68 (18)	C7B—N3B—Co1B	132.09 (18)
N4A—N3A—Co1A	121.65 (16)	N4B—N3B—Co1B	122.38 (16)
C9A—N4A—N3A	111.3 (2)	C9B—N4B—N3B	111.6 (2)
C9A—N4A—H4A	124.4	C9B—N4B—H4B	124.2
N3A—N4A—H4A	124.4	N3B—N4B—H4B	124.2
N1A—C1A—C2A	110.3 (2)	N1B—C1B—C2B	110.3 (2)
N1A—C1A—C4A	120.5 (2)	N1B—C1B—C4B	120.4 (2)
C2A—C1A—C4A	129.2 (2)	C2B—C1B—C4B	129.3 (2)
C3A—C2A—C1A	105.7 (2)	C3B—C2B—C1B	105.4 (2)
C3A—C2A—C5A	125.7 (3)	C3B—C2B—C5B	125.7 (3)
C1A—C2A—C5A	128.6 (3)	C1B—C2B—C5B	128.9 (3)
N2A—C3A—C2A	107.1 (2)	N2B—C3B—C2B	107.1 (2)
N2A—C3A—C6A	123.3 (3)	N2B—C3B—C6B	123.3 (3)
C2A—C3A—C6A	129.6 (3)	C2B—C3B—C6B	129.7 (3)
C1A—C4A—H4A1	109.5	C1B—C4B—H4B1	109.5
C1A—C4A—H4A2	109.5	C1B—C4B—H4B2	109.5
H4A1—C4A—H4A2	109.5	H4B1—C4B—H4B2	109.5
C1A—C4A—H4A3	109.5	C1B—C4B—H4B3	109.5
H4A1—C4A—H4A3	109.5	H4B1—C4B—H4B3	109.5
H4A2—C4A—H4A3	109.5	H4B2—C4B—H4B3	109.5
C2A—C5A—H5A1	109.5	C2B—C5B—H5B1	109.5
C2A—C5A—H5A2	109.5	C2B—C5B—H5B2	109.5
H5A1—C5A—H5A2	109.5	H5B1—C5B—H5B2	109.5
C2A—C5A—H5A3	109.5	C2B—C5B—H5B3	109.5
H5A1—C5A—H5A3	109.5	H5B1—C5B—H5B3	109.5
H5A2—C5A—H5A3	109.5	H5B2—C5B—H5B3	109.5
C3A—C6A—H6A1	109.5	C3B—C6B—H6B1	109.5
C3A—C6A—H6A2	109.5	C3B—C6B—H6B2	109.5
H6A1—C6A—H6A2	109.5	H6B1—C6B—H6B2	109.5
C3A—C6A—H6A3	109.5	C3B—C6B—H6B3	109.5
H6A1—C6A—H6A3	109.5	H6B1—C6B—H6B3	109.5
H6A2—C6A—H6A3	109.5	H6B2—C6B—H6B3	109.5
N3A—C7A—C8A	110.2 (2)	N3B—C7B—C8B	110.2 (2)
N3A—C7A—C10A	121.4 (2)	N3B—C7B—C10B	122.0 (2)
C8A—C7A—C10A	128.4 (2)	C8B—C7B—C10B	127.7 (2)
C9A—C8A—C7A	106.0 (2)	C9B—C8B—C7B	105.6 (2)
C9A—C8A—C11A	127.5 (2)	C9B—C8B—C11B	127.5 (2)
C7A—C8A—C11A	126.6 (2)	C7B—C8B—C11B	127.0 (2)
N4A—C9A—C8A	106.8 (2)	N4B—C9B—C8B	107.1 (2)
N4A—C9A—C12A	122.0 (2)	N4B—C9B—C12B	122.2 (2)
C8A—C9A—C12A	131.1 (2)	C8B—C9B—C12B	130.7 (2)
C7A—C10A—H10A	109.5	C7B—C10B—H10D	109.5
C7A—C10A—H10B	109.5	C7B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
C7A—C10A—H10C	109.5	C7B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
C8A—C11A—H11A	109.5	C8B—C11B—H11D	109.5
C8A—C11A—H11B	109.5	C8B—C11B—H11E	109.5
H11A—C11A—H11B	109.5	H11D—C11B—H11E	109.5
C8A—C11A—H11C	109.5	C8B—C11B—H11F	109.5
H11A—C11A—H11C	109.5	H11D—C11B—H11F	109.5
H11B—C11A—H11C	109.5	H11E—C11B—H11F	109.5
C9A—C12A—H12A	109.5	C9B—C12B—H12D	109.5
C9A—C12A—H12B	109.5	C9B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C9A—C12A—H12C	109.5	C9B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
N3A—Co1A—N1A—C1A	60.6 (3)	N3B—Co1B—N1B—C1B	59.8 (3)
Cl1A—Co1A—N1A—C1A	−51.1 (2)	Cl1B—Co1B—N1B—C1B	−55.1 (3)
Cl2A—Co1A—N1A—C1A	−179.6 (2)	Cl2B—Co1B—N1B—C1B	176.5 (2)
N3A—Co1A—N1A—N2A	−107.49 (19)	N3B—Co1B—N1B—N2B	−101.98 (19)
Cl1A—Co1A—N1A—N2A	140.83 (17)	Cl1B—Co1B—N1B—N2B	143.17 (17)
Cl2A—Co1A—N1A—N2A	12.3 (2)	Cl2B—Co1B—N1B—N2B	14.73 (19)
C1A—N1A—N2A—C3A	0.9 (3)	C1B—N1B—N2B—C3B	0.6 (3)
Co1A—N1A—N2A—C3A	171.76 (17)	Co1B—N1B—N2B—C3B	166.59 (17)
N1A—Co1A—N3A—C7A	63.9 (3)	N1B—Co1B—N3B—C7B	63.7 (3)
Cl1A—Co1A—N3A—C7A	−176.7 (2)	Cl1B—Co1B—N3B—C7B	−173.5 (2)
Cl2A—Co1A—N3A—C7A	−49.4 (3)	Cl2B—Co1B—N3B—C7B	−46.1 (3)
N1A—Co1A—N3A—N4A	−115.55 (19)	N1B—Co1B—N3B—N4B	−114.79 (19)
Cl1A—Co1A—N3A—N4A	3.8 (2)	Cl1B—Co1B—N3B—N4B	8.0 (2)
Cl2A—Co1A—N3A—N4A	131.07 (17)	Cl2B—Co1B—N3B—N4B	135.43 (18)
C7A—N3A—N4A—C9A	0.6 (3)	C7B—N3B—N4B—C9B	0.7 (3)
Co1A—N3A—N4A—C9A	−179.83 (17)	Co1B—N3B—N4B—C9B	179.50 (17)
N2A—N1A—C1A—C2A	−0.3 (3)	N2B—N1B—C1B—C2B	−0.4 (3)
Co1A—N1A—C1A—C2A	−169.78 (19)	Co1B—N1B—C1B—C2B	−164.27 (19)
N2A—N1A—C1A—C4A	178.7 (2)	N2B—N1B—C1B—C4B	178.9 (2)
Co1A—N1A—C1A—C4A	9.2 (4)	Co1B—N1B—C1B—C4B	15.0 (4)
N1A—C1A—C2A—C3A	−0.4 (3)	N1B—C1B—C2B—C3B	0.1 (3)
C4A—C1A—C2A—C3A	−179.3 (3)	C4B—C1B—C2B—C3B	−179.1 (3)
N1A—C1A—C2A—C5A	179.4 (3)	N1B—C1B—C2B—C5B	178.8 (3)
C4A—C1A—C2A—C5A	0.5 (5)	C4B—C1B—C2B—C5B	−0.4 (5)
N1A—N2A—C3A—C2A	−1.2 (3)	N1B—N2B—C3B—C2B	−0.6 (3)
N1A—N2A—C3A—C6A	179.5 (2)	N1B—N2B—C3B—C6B	179.3 (2)
C1A—C2A—C3A—N2A	0.9 (3)	C1B—C2B—C3B—N2B	0.3 (3)
C5A—C2A—C3A—N2A	−178.9 (3)	C5B—C2B—C3B—N2B	−178.5 (3)
C1A—C2A—C3A—C6A	−179.8 (3)	C1B—C2B—C3B—C6B	−179.6 (3)
C5A—C2A—C3A—C6A	0.4 (5)	C5B—C2B—C3B—C6B	1.6 (5)
N4A—N3A—C7A—C8A	−0.7 (3)	N4B—N3B—C7B—C8B	−0.8 (3)
Co1A—N3A—C7A—C8A	179.77 (19)	Co1B—N3B—C7B—C8B	−179.47 (19)
N4A—N3A—C7A—C10A	178.1 (2)	N4B—N3B—C7B—C10B	178.4 (2)
Co1A—N3A—C7A—C10A	−1.4 (4)	Co1B—N3B—C7B—C10B	−0.2 (4)
N3A—C7A—C8A—C9A	0.6 (3)	N3B—C7B—C8B—C9B	0.7 (3)
C10A—C7A—C8A—C9A	−178.1 (3)	C10B—C7B—C8B—C9B	−178.5 (3)
N3A—C7A—C8A—C11A	−178.6 (2)	N3B—C7B—C8B—C11B	−179.3 (2)
C10A—C7A—C8A—C11A	2.7 (5)	C10B—C7B—C8B—C11B	1.6 (5)
N3A—N4A—C9A—C8A	−0.2 (3)	N3B—N4B—C9B—C8B	−0.3 (3)
N3A—N4A—C9A—C12A	−177.4 (2)	N3B—N4B—C9B—C12B	−177.7 (2)
C7A—C8A—C9A—N4A	−0.2 (3)	C7B—C8B—C9B—N4B	−0.2 (3)
C11A—C8A—C9A—N4A	178.9 (3)	C11B—C8B—C9B—N4B	179.7 (3)
C7A—C8A—C9A—C12A	176.6 (3)	C7B—C8B—C9B—C12B	176.9 (3)
C11A—C8A—C9A—C12A	−4.2 (5)	C11B—C8B—C9B—C12B	−3.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A···Cl2Bi	0.88	2.55	3.290 (2)	142.
N2A—H2A···Cl2A	0.88	2.86	3.373 (2)	118.
N4A—H4A···Cl1Bii	0.88	2.61	3.416 (2)	152.
N4A—H4A···Cl1A	0.88	2.79	3.309 (2)	119.
N2B—H2B···Cl2Aiii	0.88	2.70	3.456 (2)	145.
N2B—H2B···Cl2B	0.88	2.76	3.286 (2)	119.
N4B—H4B···Cl1Aiv	0.88	2.57	3.363 (2)	150.
N4B—H4B···Cl1B	0.88	2.86	3.365 (2)	118.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2A⋯Cl2Bi	0.88	2.55	3.290 (2)	142
N2A—H2A⋯Cl2A	0.88	2.86	3.373 (2)	118
N4A—H4A⋯Cl1Bii	0.88	2.61	3.416 (2)	152
N4A—H4A⋯Cl1A	0.88	2.79	3.309 (2)	119
N2B—H2B⋯Cl2Aiii	0.88	2.70	3.456 (2)	145
N2B—H2B⋯Cl2B	0.88	2.76	3.286 (2)	119
N4B—H4B⋯Cl1Aiv	0.88	2.57	3.363 (2)	150
N4B—H4B⋯Cl1B	0.88	2.86	3.365 (2)	118

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .