Dichlorido(2-chloro-9-mesityl-1,10-phenanthroline-κN,N')cobalt(II) dichloro-methane hemisolvate.

The title compound, [CoCl(2)(C(21)H(17)ClN(2))]·0.5CH(2)Cl(2), crystallizes from dichloro-methane as a 2:1 solvate [CoCl(2)L](2)·CH(2)Cl(2) (L is 2-chloro-9-mesityl-1,10-phenanthroline). There are two independent CoCl(2)L mol-ecules in the asymmetric unit and both mol-ecules have similar conformations. They are connected by a weak C-H⋯π inter-action involving the mesityl ring. The cobalt center is four-coordinated by the two N-atom donors of the bidentate ligand and two chloride ions in a distorted tetra-hedral geometry. The packing of the mol-ecules is stabilized by weak slipped π-π stacking inter-actions between symmetry-related phenanthroline groups.

Related literature

For related literature, see: Britovsek et al. (1998 ▶); Garas & Vagg (2000 ▶); Gibson & Spitzmesser (2003 ▶); Sauvage (1990 ▶); Small & Brookhart (1998 ▶).

Experimental

Crystal data

[CoCl2(n class="Gene">C21H17ClN2)]·0.5CH2Cl2

M = 505.11

Triclinic,

a = 9.8830 (3) Å

b = 15.3591 (5) Å

c = 15.6544 (5) Å

α = 79.964 (1)°

β = 78.094 (1)°

γ = 74.515 (1)°

V = 2222.75 (12) Å3

Z = 4

Mo Kα radiation

μ = 1.26 mm−1

T = 293 (2) K

0.45 × 0.36 × 0.25 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.688, T max = 1.000 (expected range = 0.501–0.729)

13275 measured reflections

9215 independent reflections

5134 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.159

S = 1.02

9215 reflections

520 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.69 e Å−3

Data collection: n class="Gene">APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808007320/dn2321sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007320/dn2321Isup2.hkl

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

[CoCl2(C21H17ClN2)]·0.5CH2Cl2	Z = 4
Mr = 505.11	F000 = 1024
Triclinic, P1	Dx = 1.509 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.8830 (3) Å	Cell parameters from 2211 reflections
b = 15.3591 (5) Å	θ = 2.4–20.6º
c = 15.6544 (5) Å	µ = 1.26 mm−1
α = 79.964 (1)º	T = 293 (2) K
β = 78.094 (1)º	Prism, blue
γ = 74.515 (1)º	0.45 × 0.36 × 0.25 mm
V = 2222.75 (12) Å3

Bruker APEXII diffractometer	9215 independent reflections
Radiation source: fine-focus sealed tube	5134 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 293(2) K	θmax = 26.8º
ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −12→9
Tmin = 0.688, Tmax = 1.000	k = −19→18
13275 measured reflections	l = −19→17

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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.0717P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.002
9215 reflections	Δρmax = 0.44 e Å−3
520 parameters	Δρmin = −0.69 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > σ(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
Co1	0.32238 (6)	0.79829 (4)	0.05811 (4)	0.04711 (18)
Co2	0.80414 (6)	0.23178 (4)	0.34801 (4)	0.0570 (2)
Cl1	0.41735 (14)	0.98271 (9)	−0.08111 (9)	0.0757 (4)
Cl2	0.31739 (13)	0.86836 (8)	0.17136 (8)	0.0665 (3)
Cl3	0.52745 (12)	0.71461 (9)	−0.00237 (9)	0.0693 (4)
Cl4	0.7295 (2)	0.02459 (11)	0.43135 (13)	0.1119 (6)
Cl5	0.66100 (16)	0.23526 (12)	0.25601 (12)	0.0995 (5)
Cl6	0.72549 (15)	0.27227 (9)	0.48148 (9)	0.0774 (4)
Cl7	0.7761 (2)	−0.26354 (17)	0.52141 (14)	0.1424 (8)
Cl8	0.6046 (3)	−0.16227 (19)	0.3978 (2)	0.2024 (14)
N1	0.2218 (3)	0.8907 (2)	−0.0376 (2)	0.0470 (8)
N2	0.1439 (3)	0.7478 (2)	0.0720 (2)	0.0404 (8)
N3	0.9359 (4)	0.1022 (2)	0.3618 (2)	0.0610 (10)
N4	0.9946 (3)	0.2638 (2)	0.2955 (2)	0.0459 (8)
C1	0.2594 (5)	0.9605 (3)	−0.0895 (3)	0.0565 (12)
C2	0.1767 (5)	1.0170 (3)	−0.1498 (3)	0.0645 (13)
H2	0.2079	1.0651	−0.1860	0.077*
C3	0.0504 (5)	1.0002 (3)	−0.1544 (3)	0.0630 (13)
H3	−0.0062	1.0377	−0.1934	0.076*
C4	0.0039 (5)	0.9259 (3)	−0.1000 (3)	0.0495 (11)
C5	−0.1263 (5)	0.9048 (3)	−0.1012 (3)	0.0559 (11)
H5	−0.1865	0.9408	−0.1390	0.067*
C6	−0.1641 (5)	0.8330 (3)	−0.0479 (3)	0.0570 (12)
H6	−0.2493	0.8194	−0.0504	0.068*
C7	−0.0754 (4)	0.7777 (3)	0.0121 (3)	0.0486 (10)
C8	−0.1120 (5)	0.7038 (3)	0.0705 (3)	0.0597 (12)
H8	−0.1970	0.6883	0.0712	0.072*
C9	−0.0219 (5)	0.6555 (3)	0.1258 (3)	0.0561 (12)
H9	−0.0447	0.6057	0.1636	0.067*
C10	0.1054 (4)	0.6791 (3)	0.1273 (3)	0.0439 (10)
C11	0.0545 (4)	0.7974 (3)	0.0149 (3)	0.0416 (9)
C12	0.0954 (4)	0.8733 (3)	−0.0432 (3)	0.0453 (10)
C13	0.1957 (4)	0.6275 (3)	0.1945 (3)	0.0426 (10)
C14	0.1613 (5)	0.6522 (3)	0.2786 (3)	0.0534 (11)
C15	0.2371 (5)	0.6000 (4)	0.3422 (3)	0.0643 (13)
H15	0.2143	0.6169	0.3986	0.077*
C16	0.3449 (5)	0.5241 (3)	0.3256 (3)	0.0636 (13)
C17	0.3784 (4)	0.5010 (3)	0.2401 (3)	0.0590 (12)
H17	0.4514	0.4501	0.2274	0.071*
C18	0.3066 (4)	0.5515 (3)	0.1736 (3)	0.0468 (10)
C19	0.0407 (6)	0.7335 (4)	0.3020 (3)	0.0854 (17)
H19A	0.0311	0.7392	0.3632	0.128*
H19B	−0.0465	0.7250	0.2907	0.128*
H19C	0.0612	0.7878	0.2670	0.128*
C20	0.4251 (6)	0.4690 (4)	0.3969 (4)	0.101 (2)
H20A	0.4882	0.5018	0.4085	0.152*
H20B	0.4794	0.4118	0.3781	0.152*
H20C	0.3588	0.4584	0.4495	0.152*
C21	0.3423 (5)	0.5227 (3)	0.0829 (3)	0.0688 (14)
H21A	0.4169	0.4679	0.0819	0.103*
H21B	0.3734	0.5701	0.0411	0.103*
H21C	0.2593	0.5119	0.0679	0.103*
C22	0.9067 (6)	0.0232 (3)	0.3965 (3)	0.0731 (15)
C23	1.0084 (9)	−0.0587 (4)	0.4057 (4)	0.094 (2)
H23	0.9818	−0.1125	0.4306	0.113*
C24	1.1494 (8)	−0.0579 (4)	0.3770 (4)	0.091 (2)
H24	1.2194	−0.1118	0.3828	0.109*
C25	1.1888 (6)	0.0243 (3)	0.3387 (3)	0.0717 (15)
C26	1.3299 (6)	0.0325 (4)	0.3070 (4)	0.0821 (17)
H26	1.4042	−0.0194	0.3092	0.099*
C27	1.3598 (6)	0.1128 (4)	0.2739 (4)	0.0818 (17)
H27	1.4544	0.1155	0.2547	0.098*
C28	1.2495 (5)	0.1951 (3)	0.2671 (3)	0.0598 (12)
C29	1.2745 (5)	0.2805 (4)	0.2325 (3)	0.0695 (14)
H29	1.3666	0.2873	0.2107	0.083*
C30	1.1608 (5)	0.3536 (3)	0.2314 (3)	0.0642 (13)
H30	1.1763	0.4109	0.2087	0.077*
C31	1.0218 (4)	0.3453 (3)	0.2633 (3)	0.0478 (10)
C32	1.1082 (5)	0.1893 (3)	0.2975 (3)	0.0511 (11)
C33	1.0767 (5)	0.1025 (3)	0.3340 (3)	0.0558 (12)
C34	0.8998 (4)	0.4272 (3)	0.2636 (3)	0.0459 (10)
C35	0.8679 (5)	0.4817 (3)	0.3307 (3)	0.0503 (11)
C36	0.7599 (5)	0.5611 (3)	0.3259 (3)	0.0579 (12)
H36	0.7384	0.5983	0.3701	0.069*
C37	0.6836 (5)	0.5861 (3)	0.2567 (3)	0.0577 (12)
C38	0.7163 (5)	0.5302 (3)	0.1918 (3)	0.0574 (12)
H38	0.6648	0.5458	0.1457	0.069*
C39	0.8230 (5)	0.4519 (3)	0.1937 (3)	0.0537 (11)
C40	0.9502 (5)	0.4564 (3)	0.4063 (3)	0.0662 (13)
H40A	0.9447	0.3965	0.4345	0.099*
H40B	0.9102	0.4994	0.4479	0.099*
H40C	1.0481	0.4573	0.3844	0.099*
C41	0.5680 (5)	0.6738 (3)	0.2527 (4)	0.0894 (18)
H41A	0.5216	0.6852	0.3113	0.134*
H41B	0.4995	0.6684	0.2197	0.134*
H41C	0.6098	0.7234	0.2245	0.134*
C42	0.8605 (6)	0.3948 (4)	0.1182 (3)	0.0828 (16)
H42A	0.7796	0.4059	0.0893	0.124*
H42B	0.8866	0.3314	0.1407	0.124*
H42C	0.9390	0.4110	0.0769	0.124*
C43	0.6125 (7)	−0.2104 (6)	0.5048 (6)	0.152 (3)
H43A	0.5746	−0.1630	0.5431	0.182*
H43B	0.5526	−0.2534	0.5209	0.182*

	U11	U22	U33	U12	U13	U23
Co1	0.0409 (3)	0.0501 (3)	0.0512 (4)	−0.0109 (3)	−0.0104 (3)	−0.0055 (3)
Co2	0.0542 (4)	0.0565 (4)	0.0653 (4)	−0.0192 (3)	−0.0143 (3)	−0.0068 (3)
Cl1	0.0669 (8)	0.0820 (9)	0.0832 (9)	−0.0381 (7)	−0.0056 (7)	−0.0007 (7)
Cl2	0.0776 (8)	0.0572 (7)	0.0661 (8)	−0.0037 (6)	−0.0261 (7)	−0.0147 (6)
Cl3	0.0477 (7)	0.0725 (8)	0.0851 (9)	−0.0073 (6)	−0.0034 (6)	−0.0230 (7)
Cl4	0.1371 (15)	0.0841 (11)	0.1283 (15)	−0.0663 (10)	−0.0125 (12)	0.0002 (10)
Cl5	0.0840 (10)	0.1128 (12)	0.1225 (13)	−0.0340 (9)	−0.0530 (10)	−0.0117 (10)
Cl6	0.0909 (10)	0.0705 (8)	0.0697 (8)	−0.0218 (7)	−0.0053 (7)	−0.0116 (7)
Cl7	0.1138 (15)	0.187 (2)	0.1112 (15)	−0.0117 (14)	−0.0297 (12)	−0.0040 (14)
Cl8	0.218 (3)	0.149 (2)	0.278 (4)	−0.063 (2)	−0.165 (3)	0.049 (2)
N1	0.045 (2)	0.047 (2)	0.047 (2)	−0.0096 (16)	−0.0074 (16)	−0.0038 (17)
N2	0.0408 (18)	0.0408 (18)	0.0384 (18)	−0.0072 (15)	−0.0076 (15)	−0.0043 (15)
N3	0.086 (3)	0.045 (2)	0.056 (2)	−0.019 (2)	−0.016 (2)	−0.0078 (18)
N4	0.048 (2)	0.044 (2)	0.047 (2)	−0.0085 (17)	−0.0143 (16)	−0.0060 (16)
C1	0.060 (3)	0.056 (3)	0.051 (3)	−0.019 (2)	−0.002 (2)	0.001 (2)
C2	0.080 (4)	0.051 (3)	0.059 (3)	−0.019 (3)	−0.011 (3)	0.007 (2)
C3	0.073 (3)	0.056 (3)	0.059 (3)	−0.008 (3)	−0.026 (3)	0.003 (2)
C4	0.056 (3)	0.042 (2)	0.049 (3)	−0.008 (2)	−0.012 (2)	−0.002 (2)
C5	0.057 (3)	0.054 (3)	0.057 (3)	−0.004 (2)	−0.026 (2)	−0.003 (2)
C6	0.051 (3)	0.056 (3)	0.069 (3)	−0.008 (2)	−0.028 (2)	−0.006 (2)
C7	0.046 (2)	0.048 (2)	0.052 (3)	−0.011 (2)	−0.012 (2)	−0.003 (2)
C8	0.046 (3)	0.061 (3)	0.077 (3)	−0.020 (2)	−0.020 (2)	0.003 (3)
C9	0.052 (3)	0.054 (3)	0.065 (3)	−0.022 (2)	−0.019 (2)	0.010 (2)
C10	0.041 (2)	0.046 (2)	0.043 (2)	−0.0092 (19)	−0.0081 (19)	−0.0029 (19)
C11	0.036 (2)	0.044 (2)	0.044 (2)	−0.0037 (18)	−0.0097 (19)	−0.0082 (19)
C12	0.042 (2)	0.045 (2)	0.045 (2)	−0.0051 (19)	−0.007 (2)	−0.0073 (19)
C13	0.046 (2)	0.044 (2)	0.042 (2)	−0.0171 (19)	−0.0109 (19)	−0.0014 (19)
C14	0.058 (3)	0.057 (3)	0.046 (3)	−0.020 (2)	−0.003 (2)	−0.007 (2)
C15	0.076 (3)	0.081 (4)	0.041 (3)	−0.034 (3)	−0.008 (3)	−0.001 (3)
C16	0.070 (3)	0.069 (3)	0.058 (3)	−0.031 (3)	−0.028 (3)	0.015 (3)
C17	0.044 (3)	0.048 (3)	0.085 (4)	−0.009 (2)	−0.020 (3)	0.002 (2)
C18	0.041 (2)	0.046 (2)	0.052 (3)	−0.012 (2)	−0.006 (2)	−0.003 (2)
C19	0.099 (4)	0.077 (4)	0.071 (4)	−0.010 (3)	0.010 (3)	−0.030 (3)
C20	0.102 (5)	0.123 (5)	0.085 (4)	−0.042 (4)	−0.056 (4)	0.044 (4)
C21	0.079 (3)	0.061 (3)	0.060 (3)	−0.009 (3)	−0.002 (3)	−0.017 (2)
C22	0.107 (4)	0.055 (3)	0.065 (3)	−0.027 (3)	−0.019 (3)	−0.007 (3)
C23	0.163 (7)	0.044 (3)	0.075 (4)	−0.028 (4)	−0.019 (4)	−0.006 (3)
C24	0.144 (6)	0.048 (3)	0.072 (4)	0.006 (4)	−0.031 (4)	−0.012 (3)
C25	0.098 (4)	0.057 (3)	0.057 (3)	0.006 (3)	−0.031 (3)	−0.017 (2)
C26	0.075 (4)	0.078 (4)	0.086 (4)	0.021 (3)	−0.033 (3)	−0.025 (3)
C27	0.057 (3)	0.094 (4)	0.093 (4)	0.006 (3)	−0.021 (3)	−0.035 (4)
C28	0.050 (3)	0.068 (3)	0.059 (3)	0.003 (2)	−0.017 (2)	−0.020 (2)
C29	0.058 (3)	0.079 (4)	0.076 (4)	−0.024 (3)	−0.011 (3)	−0.011 (3)
C30	0.056 (3)	0.062 (3)	0.077 (4)	−0.022 (3)	−0.012 (3)	−0.002 (3)
C31	0.049 (3)	0.051 (3)	0.046 (2)	−0.011 (2)	−0.017 (2)	−0.005 (2)
C32	0.053 (3)	0.055 (3)	0.048 (3)	−0.010 (2)	−0.014 (2)	−0.011 (2)
C33	0.066 (3)	0.051 (3)	0.052 (3)	−0.003 (2)	−0.024 (2)	−0.011 (2)
C34	0.051 (2)	0.045 (2)	0.044 (2)	−0.016 (2)	−0.016 (2)	0.0045 (19)
C35	0.055 (3)	0.054 (3)	0.046 (3)	−0.019 (2)	−0.014 (2)	−0.002 (2)
C36	0.060 (3)	0.050 (3)	0.064 (3)	−0.017 (2)	−0.005 (3)	−0.010 (2)
C37	0.048 (3)	0.050 (3)	0.073 (3)	−0.015 (2)	−0.017 (2)	0.007 (2)
C38	0.050 (3)	0.055 (3)	0.071 (3)	−0.016 (2)	−0.026 (2)	0.007 (2)
C39	0.061 (3)	0.059 (3)	0.048 (3)	−0.023 (2)	−0.017 (2)	0.000 (2)
C40	0.075 (3)	0.073 (3)	0.059 (3)	−0.022 (3)	−0.027 (3)	−0.006 (3)
C41	0.064 (3)	0.060 (3)	0.134 (5)	−0.002 (3)	−0.022 (3)	0.002 (3)
C42	0.101 (4)	0.087 (4)	0.067 (3)	−0.013 (3)	−0.036 (3)	−0.013 (3)
C43	0.092 (5)	0.168 (8)	0.167 (8)	−0.005 (5)	−0.021 (5)	0.014 (7)

Co1—N2	2.067 (3)	C19—H19A	0.9600
Co1—N1	2.090 (3)	C19—H19B	0.9600
Co1—Cl3	2.2130 (12)	C19—H19C	0.9600
Co1—Cl2	2.2146 (13)	C20—H20A	0.9600
Co2—N4	2.043 (3)	C20—H20B	0.9600
Co2—N3	2.071 (4)	C20—H20C	0.9600
Co2—Cl5	2.2028 (16)	C21—H21A	0.9600
Co2—Cl6	2.2092 (15)	C21—H21B	0.9600
Cl1—C1	1.719 (5)	C21—H21C	0.9600
Cl4—C22	1.719 (6)	C22—C23	1.391 (8)
Cl7—C43	1.656 (7)	C23—C24	1.376 (8)
Cl8—C43	1.717 (8)	C23—H23	0.9300
N1—C1	1.315 (5)	C24—C25	1.418 (8)
N1—C12	1.369 (5)	C24—H24	0.9300
N2—C10	1.329 (5)	C25—C33	1.403 (6)
N2—C11	1.375 (5)	C25—C26	1.412 (7)
N3—C22	1.319 (6)	C26—C27	1.336 (7)
N3—C33	1.371 (6)	C26—H26	0.9300
N4—C31	1.341 (5)	C27—C28	1.436 (7)
N4—C32	1.373 (5)	C27—H27	0.9300
C1—C2	1.402 (6)	C28—C29	1.395 (7)
C2—C3	1.359 (6)	C28—C32	1.401 (6)
C2—H2	0.9300	C29—C30	1.361 (7)
C3—C4	1.421 (6)	C29—H29	0.9300
C3—H3	0.9300	C30—C31	1.393 (6)
C4—C12	1.397 (6)	C30—H30	0.9300
C4—C5	1.412 (6)	C31—C34	1.492 (6)
C5—C6	1.350 (6)	C32—C33	1.443 (6)
C5—H5	0.9300	C34—C35	1.389 (6)
C6—C7	1.428 (6)	C34—C39	1.400 (6)
C6—H6	0.9300	C35—C36	1.392 (6)
C7—C11	1.405 (5)	C35—C40	1.510 (6)
C7—C8	1.406 (6)	C36—C37	1.388 (6)
C8—C9	1.355 (6)	C36—H36	0.9300
C8—H8	0.9300	C37—C38	1.376 (6)
C9—C10	1.404 (6)	C37—C41	1.517 (6)
C9—H9	0.9300	C38—C39	1.372 (6)
C10—C13	1.500 (5)	C38—H38	0.9300
C11—C12	1.442 (5)	C39—C42	1.520 (6)
C13—C14	1.384 (6)	C40—H40A	0.9600
C13—C18	1.405 (5)	C40—H40B	0.9600
C14—C15	1.380 (6)	C40—H40C	0.9600
C14—C19	1.516 (6)	C41—H41A	0.9600
C15—C16	1.375 (7)	C41—H41B	0.9600
C15—H15	0.9300	C41—H41C	0.9600
C16—C17	1.396 (6)	C42—H42A	0.9600
C16—C20	1.505 (7)	C42—H42B	0.9600
C17—C18	1.386 (6)	C42—H42C	0.9600
C17—H17	0.9300	C43—H43A	0.9700
C18—C21	1.504 (6)	C43—H43B	0.9700
N2—Co1—N1	81.74 (13)	C16—C20—H20C	109.5
N2—Co1—Cl3	117.08 (9)	H20A—C20—H20C	109.5
N1—Co1—Cl3	110.81 (10)	H20B—C20—H20C	109.5
N2—Co1—Cl2	111.88 (9)	C18—C21—H21A	109.5
N1—Co1—Cl2	109.88 (10)	C18—C21—H21B	109.5
Cl3—Co1—Cl2	119.14 (5)	H21A—C21—H21B	109.5
N4—Co2—N3	81.41 (15)	C18—C21—H21C	109.5
N4—Co2—Cl5	117.29 (11)	H21A—C21—H21C	109.5
N3—Co2—Cl5	108.36 (12)	H21B—C21—H21C	109.5
N4—Co2—Cl6	111.17 (10)	N3—C22—C23	124.5 (6)
N3—Co2—Cl6	107.10 (11)	N3—C22—Cl4	116.2 (4)
Cl5—Co2—Cl6	122.82 (7)	C23—C22—Cl4	119.3 (5)
C1—N1—C12	117.8 (4)	C24—C23—C22	118.1 (5)
C1—N1—Co1	130.8 (3)	C24—C23—H23	120.9
C12—N1—Co1	111.4 (3)	C22—C23—H23	120.9
C10—N2—C11	118.7 (3)	C23—C24—C25	120.5 (5)
C10—N2—Co1	129.9 (3)	C23—C24—H24	119.7
C11—N2—Co1	111.3 (2)	C25—C24—H24	119.7
C22—N3—C33	117.0 (4)	C33—C25—C26	119.0 (5)
C22—N3—Co2	130.8 (4)	C33—C25—C24	115.9 (6)
C33—N3—Co2	112.0 (3)	C26—C25—C24	125.0 (5)
C31—N4—C32	117.9 (4)	C27—C26—C25	121.9 (5)
C31—N4—Co2	129.3 (3)	C27—C26—H26	119.1
C32—N4—Co2	112.8 (3)	C25—C26—H26	119.1
N1—C1—C2	123.2 (4)	C26—C27—C28	121.6 (5)
N1—C1—Cl1	117.5 (4)	C26—C27—H27	119.2
C2—C1—Cl1	119.2 (4)	C28—C27—H27	119.2
C3—C2—C1	118.8 (4)	C29—C28—C32	118.0 (4)
C3—C2—H2	120.6	C29—C28—C27	124.0 (5)
C1—C2—H2	120.6	C32—C28—C27	118.0 (5)
C2—C3—C4	120.6 (4)	C30—C29—C28	118.3 (5)
C2—C3—H3	119.7	C30—C29—H29	120.8
C4—C3—H3	119.7	C28—C29—H29	120.8
C12—C4—C5	120.7 (4)	C29—C30—C31	122.0 (5)
C12—C4—C3	115.8 (4)	C29—C30—H30	119.0
C5—C4—C3	123.5 (4)	C31—C30—H30	119.0
C6—C5—C4	120.5 (4)	N4—C31—C30	120.9 (4)
C6—C5—H5	119.7	N4—C31—C34	118.4 (4)
C4—C5—H5	119.7	C30—C31—C34	120.7 (4)
C5—C6—C7	121.0 (4)	N4—C32—C28	122.9 (4)
C5—C6—H6	119.5	N4—C32—C33	116.9 (4)
C7—C6—H6	119.5	C28—C32—C33	120.2 (4)
C11—C7—C8	117.4 (4)	N3—C33—C25	123.9 (5)
C11—C7—C6	119.6 (4)	N3—C33—C32	116.8 (4)
C8—C7—C6	123.1 (4)	C25—C33—C32	119.3 (5)
C9—C8—C7	119.1 (4)	C35—C34—C39	120.1 (4)
C9—C8—H8	120.4	C35—C34—C31	119.9 (4)
C7—C8—H8	120.4	C39—C34—C31	119.9 (4)
C8—C9—C10	121.3 (4)	C34—C35—C36	118.5 (4)
C8—C9—H9	119.3	C34—C35—C40	120.9 (4)
C10—C9—H9	119.3	C36—C35—C40	120.7 (4)
N2—C10—C9	120.9 (4)	C37—C36—C35	121.8 (4)
N2—C10—C13	120.1 (3)	C37—C36—H36	119.1
C9—C10—C13	119.0 (4)	C35—C36—H36	119.1
N2—C11—C7	122.5 (4)	C38—C37—C36	118.5 (4)
N2—C11—C12	118.3 (3)	C38—C37—C41	121.1 (5)
C7—C11—C12	119.1 (4)	C36—C37—C41	120.4 (5)
N1—C12—C4	123.8 (4)	C39—C38—C37	121.5 (4)
N1—C12—C11	117.2 (4)	C39—C38—H38	119.2
C4—C12—C11	119.0 (4)	C37—C38—H38	119.2
C14—C13—C18	120.9 (4)	C38—C39—C34	119.6 (4)
C14—C13—C10	118.8 (4)	C38—C39—C42	119.7 (4)
C18—C13—C10	120.1 (4)	C34—C39—C42	120.6 (4)
C15—C14—C13	118.7 (4)	C35—C40—H40A	109.5
C15—C14—C19	120.0 (4)	C35—C40—H40B	109.5
C13—C14—C19	121.3 (4)	H40A—C40—H40B	109.5
C16—C15—C14	122.8 (4)	C35—C40—H40C	109.5
C16—C15—H15	118.6	H40A—C40—H40C	109.5
C14—C15—H15	118.6	H40B—C40—H40C	109.5
C15—C16—C17	117.5 (4)	C37—C41—H41A	109.5
C15—C16—C20	121.1 (5)	C37—C41—H41B	109.5
C17—C16—C20	121.4 (5)	H41A—C41—H41B	109.5
C18—C17—C16	122.1 (4)	C37—C41—H41C	109.5
C18—C17—H17	118.9	H41A—C41—H41C	109.5
C16—C17—H17	118.9	H41B—C41—H41C	109.5
C17—C18—C13	118.0 (4)	C39—C42—H42A	109.5
C17—C18—C21	120.7 (4)	C39—C42—H42B	109.5
C13—C18—C21	121.3 (4)	H42A—C42—H42B	109.5
C14—C19—H19A	109.5	C39—C42—H42C	109.5
C14—C19—H19B	109.5	H42A—C42—H42C	109.5
H19A—C19—H19B	109.5	H42B—C42—H42C	109.5
C14—C19—H19C	109.5	Cl7—C43—Cl8	113.2 (5)
H19A—C19—H19C	109.5	Cl7—C43—H43A	108.9
H19B—C19—H19C	109.5	Cl8—C43—H43A	108.9
C16—C20—H20A	109.5	Cl7—C43—H43B	108.9
C16—C20—H20B	109.5	Cl8—C43—H43B	108.9
H20A—C20—H20B	109.5	H43A—C43—H43B	107.8

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg1i	0.93	2.59	3.470 (5)	157

	Centroid–centroid	α	CgI-perp	CgJ-perp	slippage
Cg2 – Cg2i	3.877 (3)	0.0	3.712	3.712	1.12
Cg2 – Cg3i	3.923 (3)	0.49	3.712	3.701	1.23
Cg4 – Cg4ii	3.992 (3)	0.02	3.490	3.490	1.94

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg1i	0.93	2.59	3.470 (5)	157

Symmetry code: (i) . Cg1 is the centroid of the mesityl ring.

Table 2

Possible π–π stacking interactions (Å, °)

	Centroid–centroid	α	CgI-perp	CgJ-perp	slippage
Cg2 – Cg2i	3.877 (3)	0.0	3.712	3.712	1.12
Cg2 – Cg3i	3.923 (3)	0.49	3.712	3.701	1.23
Cg4 – Cg4ii	3.992 (3)	0.02	3.490	3.490	1.94

Symmetry codes: (i) ; (ii) . CgI –CgJ = distance between ring centroids; α = dihedral angle between planes I and J; CgI–perp = perpendicular distance of Cg(I) from ring J; CgJ-perp = perpendicular distance of Cg(J) from ring I; slippage = distance between Cg(I) and perpendicular projection of Cg(J) on ring I. Cg2 is the centroid of atoms N1,C1–C4,C12; Cg3 is the centroid of atoms C4–C7,C11,C12; Cg4 is the centroid of atoms N3,C22–C25,C33.