Aqua­nitro(α,β,γ,δ-tetra­phenyl­porphyrinato)­cobalt(III) di­chloro­methane solvate

In the crystal structure of the title compound, [Co(NO₂)(C₄₄H₂₈N₄)(H₂O)]·CH₂Cl₂, the Co^III atom has a distorted octahedral coordination, with the water mol­ecule trans to the nitro ligand. The Co—N(nitro) and Co—O(aqua) bond distances are 1.863 (8) and 2.114 (8) Å, respectively. There is no intermolecular hydrogen bond involving the aqua ligand.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.089
• wR factor = 0.317
• Data-to-parameter ratio = 13.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



PLAT_420  Alert B D-H Without Acceptor       O(6)   -   H(6A)             ?

Author response: see the last part of _publ_section_comment

PLAT_420  Alert B D-H Without Acceptor       O(6)   -   H(6B)             ?

Author response: see the last part of _publ_section_comment

 Alert Level C:



RFACR_01  Alert C The value of the weighted R factor is > 0.25
          Weighted R factor given   0.317


 0 Alert Level A = Potentially serious problem

 2 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

S1. Comment

The nitro-to-nitrito photoisomerization of the title complex, [Co(tpp)(NO₂)], where tpp is α,β,γ,δ-tetraphenylporphyrinate, was investigated in a benzene solution using the laser flash technique (Seki et al., 1997). The crystals grown from a dimethylformamide (DMF) solution, were determined to be [Co(tpp)(NO₂)(H₂O)]·2DMF and there was orientational disorder such that the positions of the nitro and aqua ligands were exchanged (Ohba et al., 2000). The crystal structure of [Co(tpp)(NO₂)].benzene, has also been determined recently to reveal that there is no aqua ligand in the compound obtained from a benzene solution (Ohba & Seki, 2002). The present paper reports the structure of the title crystal, [Co(tpp)(NO₂)(H₂O)].dichloromethane, (I), which was grown from a dichloromethane solution.

The Co atom has an distorted octahedral coordination with the water molecule at the trans position to the nitro ligand (Fig. 1). The Co1 atom is shifted by 0.072 (4) Å from the N8/N9/N10/N11 coordination plane toward the nitro ligand. In the tpp coordination plane, the N8—Co1—N10 and N9—Co1—N11 linkages are almost linear, 174.5 (3)–177.1 (3)°, with Co—N bond distances in the range 1.954 (7)–1.977 (6) Å (Table 1). The pyrrole ring moieties involving the N8 and N10 atoms are bent opposite to the nitro group, and those involving the N9 and N11 atoms are bent towards the nitro group. The dihedral angles between the N8/N9/N10/N11 plane and the pyrrole rings are 6.7 (3), 8.6 (3), 6.1 (3), and 8.6 (3)° for the N8, N9, N10, and N11 pyrrole rings, respectively.

The Co1—N7(nitro) bond length is 1.863 (8) Å, which is comparable to that of 1.880 (3) Å in [Co(tpp)(NO₂)].benzene (Ohba & Seki, 2002). The Co1—O6(aqua) bond distance is 2.114 (8) Å, which is apparently longer than those in other Co^III(tpp) complexes, 1.932 (8)–1.979 (3) Å (Masuda et al., 1982; Iimura et al., 1988). There is no intermolecular hydrogen bond involving the aqua ligand. The O6 atom is surrounded by the phenyl groups of neighboring complexes in the crystal (Table 2 and Fig. 2).

S2. Experimental

The preparation of the title complex has been described previously (Seki et al., 1997). Crystals were grown from a dichloromethane solution.

S3. Refinement

The crystal specimen was sealed in a capillary with the mother liquor to avoid efflorescence. However, the intensity of the standard reflections decayed 36%, which was corrected. All H-atom positional parameters were calculated geometrically and fixed with U_iso(H) = 1.2U_eq(parent atom). The positions of the aqua H atoms were calculated assuming the O sp² hybridization based on a suitable peak in difference synthesis. The largely elongated displacement ellipsoid of the C12, which is the central C atom of the dichloromethane molecule, suggests the positional disorder, although a refinement of the split-atom model was unsuccessful.

Computing details

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures

	Fig. 1. The molecular structure of (I) with displacement ellipsoids plotted at the 50% probability level.
	Fig. 2. The projection of the crystal structure of (I) along c.

(I)

Crystal data

[Co(NO2)(C44H28N4)(H2O)]·CH2Cl2	F(000) = 1688.0
Mr = 820.62	Dx = 1.444 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.7107 Å
a = 14.713 (3) Å	Cell parameters from 24 reflections
b = 19.540 (6) Å	θ = 11.0–12.1°
c = 13.413 (4) Å	µ = 0.65 mm^−1
β = 101.74 (2)°	T = 297 K
V = 3775.5 (19) Å^3	Plate, purple
Z = 4	0.3 × 0.3 × 0.3 mm

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.055
θ–2θ scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: integration (Coppens et al, 1965)	h = 0→17
Tmin = 0.820, Tmax = 0.857	k = 0→23
9711 measured reflections	l = −15→15
6636 independent reflections	3 standard reflections every 150 reflections
3288 reflections with I > 2σ(I)	intensity decay: 36.3%

Refinement

Refinement on F^2	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.089	w = 1/[σ^2(Fo^2) + (0.1368P)^2 + 20.8126P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.317	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.60 e Å^−3
6636 reflections	Δρmin = −1.22 e Å^−3
505 parameters

Special details

Refinement. Refinement using reflections with F² > -10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Co1	0.22482 (7)	0.37668 (6)	0.19449 (8)	0.0395 (4)
Cl2	0.2092 (3)	0.7213 (2)	0.1995 (3)	0.108 (1)
Cl3	0.3224 (3)	0.7128 (3)	0.4003 (3)	0.127 (2)
O4	0.1998 (5)	0.5049 (3)	0.1179 (6)	0.067 (2)
O5	0.2781 (5)	0.5013 (4)	0.2709 (6)	0.076 (2)
O6	0.2164 (5)	0.2687 (4)	0.1954 (5)	0.070 (2)
N7	0.2353 (5)	0.4717 (4)	0.1948 (6)	0.052 (2)
N8	0.0919 (5)	0.3757 (4)	0.1283 (5)	0.046 (2)
N9	0.2587 (4)	0.3735 (4)	0.0606 (5)	0.045 (2)
N10	0.3557 (5)	0.3681 (4)	0.2599 (5)	0.048 (2)
N11	0.1898 (5)	0.3748 (4)	0.3291 (5)	0.047 (2)
C12	0.269 (1)	0.6672 (6)	0.293 (2)	0.152 (9)
C13	0.0166 (6)	0.3702 (5)	0.1763 (7)	0.050 (2)
C14	−0.0678 (6)	0.3687 (6)	0.1001 (7)	0.056 (3)
C15	−0.0450 (6)	0.3739 (6)	0.0093 (6)	0.056 (2)
C16	0.0547 (5)	0.3794 (5)	0.0258 (6)	0.044 (2)
C17	0.1037 (5)	0.3862 (5)	−0.0501 (6)	0.043 (2)
C18	0.1997 (6)	0.3844 (5)	−0.0347 (6)	0.049 (2)
C19	0.2535 (6)	0.3923 (5)	−0.1107 (6)	0.054 (3)
C20	0.3417 (6)	0.3850 (5)	−0.0665 (7)	0.053 (2)
C21	0.3459 (5)	0.3744 (5)	0.0397 (6)	0.047 (2)
C22	0.4277 (5)	0.3647 (5)	0.1103 (6)	0.045 (2)
C23	0.4317 (5)	0.3607 (5)	0.2133 (6)	0.048 (2)
C24	0.5162 (6)	0.3530 (6)	0.2887 (7)	0.057 (3)
C25	0.4928 (6)	0.3606 (6)	0.3808 (7)	0.056 (3)
C26	0.3940 (6)	0.3704 (5)	0.3635 (6)	0.046 (2)
C27	0.3462 (5)	0.3801 (4)	0.4415 (6)	0.038 (2)
C28	0.2517 (6)	0.3829 (5)	0.4221 (6)	0.044 (2)
C29	0.1982 (7)	0.3899 (6)	0.5016 (6)	0.060 (3)
C30	0.1076 (6)	0.3863 (7)	0.4574 (6)	0.066 (3)
C31	0.1017 (6)	0.3758 (6)	0.3496 (6)	0.051 (2)
C32	0.0202 (5)	0.3709 (5)	0.2791 (6)	0.048 (2)
C33	0.0509 (6)	0.3914 (5)	−0.1583 (6)	0.045 (2)
C34	−0.0101 (6)	0.4442 (5)	−0.1889 (7)	0.052 (2)
C35	−0.0618 (6)	0.4482 (5)	−0.2888 (7)	0.056 (3)
C36	−0.0517 (7)	0.3988 (6)	−0.3580 (7)	0.061 (3)
C37	0.0068 (7)	0.3438 (6)	−0.3283 (7)	0.059 (3)
C38	0.0575 (7)	0.3409 (5)	−0.2301 (7)	0.053 (2)
C39	0.5169 (6)	0.3634 (5)	0.0721 (6)	0.051 (2)
C40	0.5742 (8)	0.4199 (7)	0.0831 (9)	0.080 (4)
C41	0.6534 (7)	0.4215 (7)	0.0433 (9)	0.079 (4)
C42	0.6786 (6)	0.3653 (6)	−0.0046 (7)	0.059 (3)
C43	0.6235 (7)	0.3092 (6)	−0.0163 (8)	0.063 (3)
C44	0.5419 (6)	0.3066 (5)	0.0216 (8)	0.059 (3)
C45	0.3995 (6)	0.3885 (5)	0.5475 (6)	0.047 (2)
C46	0.4373 (8)	0.4510 (6)	0.5805 (8)	0.069 (3)
C47	0.4886 (8)	0.4600 (6)	0.6776 (8)	0.075 (3)
C48	0.5014 (7)	0.4052 (6)	0.7444 (8)	0.062 (3)
C49	0.4634 (8)	0.3448 (6)	0.7139 (7)	0.071 (3)
C50	0.4097 (7)	0.3347 (6)	0.6156 (8)	0.067 (3)
C51	−0.0702 (5)	0.3723 (5)	0.3166 (6)	0.048 (2)
C52	−0.1256 (7)	0.4295 (6)	0.3049 (9)	0.075 (3)
C53	−0.2088 (8)	0.4281 (8)	0.342 (1)	0.087 (4)
C54	−0.2335 (6)	0.3708 (7)	0.3886 (8)	0.070 (3)
C55	−0.1777 (8)	0.3154 (6)	0.4004 (8)	0.067 (3)
C56	−0.0976 (7)	0.3164 (5)	0.3643 (7)	0.058 (3)
H6A	0.2577	0.2420	0.1659	0.0814*
H6B	0.1706	0.2452	0.2248	0.0814*
H12A	0.2269	0.6352	0.3112	0.1828*
H12B	0.3153	0.6434	0.2660	0.1828*
H14	−0.1289	0.3647	0.1123	0.0677*
H15	−0.0869	0.3740	−0.0548	0.0673*
H19	0.2301	0.4013	−0.1809	0.0648*
H20	0.3931	0.3866	−0.0994	0.0633*
H24	0.5764	0.3443	0.2763	0.0681*
H25	0.5342	0.3597	0.4451	0.0672*
H29	0.2229	0.3959	0.5721	0.0723*
H30	0.0568	0.3899	0.4909	0.0790*
H34	−0.0172	0.4789	−0.1414	0.0629*
H35	−0.1039	0.4850	−0.3083	0.0668*
H36	−0.0847	0.4023	−0.4265	0.0733*
H37	0.0119	0.3084	−0.3752	0.0704*
H38	0.0984	0.3033	−0.2105	0.0638*
H40	0.5587	0.4586	0.1191	0.0965*
H41	0.6902	0.4618	0.0491	0.0955*
H42	0.7346	0.3655	−0.0296	0.0703*
H43	0.6407	0.2705	−0.0512	0.0758*
H44	0.5043	0.2667	0.0131	0.0707*
H46	0.4279	0.4888	0.5350	0.0829*
H47	0.5145	0.5035	0.6987	0.0904*
H48	0.5373	0.4104	0.8113	0.0746*
H49	0.4726	0.3074	0.7602	0.0849*
H50	0.3813	0.2918	0.5965	0.0812*
H52	−0.1084	0.4693	0.2723	0.0901*
H53	−0.2477	0.4673	0.3349	0.1045*
H54	−0.2900	0.3700	0.4124	0.0841*
H55	−0.1941	0.2758	0.4338	0.0802*
H56	−0.0594	0.2769	0.3726	0.0697*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0330 (6)	0.0526 (7)	0.0334 (6)	0.0025 (6)	0.0078 (4)	−0.0002 (6)
Cl2	0.090 (2)	0.131 (3)	0.099 (3)	0.014 (2)	0.011 (2)	−0.021 (2)
Cl3	0.101 (3)	0.186 (5)	0.092 (3)	0.001 (3)	0.016 (2)	0.031 (3)
O4	0.082 (5)	0.051 (4)	0.066 (5)	0.007 (4)	0.014 (4)	0.011 (4)
O5	0.077 (5)	0.067 (5)	0.074 (5)	−0.007 (4)	−0.007 (4)	−0.016 (4)
O6	0.069 (5)	0.077 (5)	0.060 (4)	0.004 (4)	0.010 (4)	0.005 (4)
N7	0.043 (4)	0.065 (5)	0.048 (4)	0.003 (4)	0.009 (4)	0.001 (4)
N8	0.045 (4)	0.062 (5)	0.034 (4)	−0.004 (4)	0.017 (3)	−0.002 (4)
N9	0.029 (3)	0.067 (5)	0.037 (4)	0.007 (4)	0.004 (3)	0.001 (4)
N10	0.049 (4)	0.066 (5)	0.031 (4)	−0.005 (4)	0.010 (3)	−0.003 (4)
N11	0.044 (4)	0.064 (5)	0.035 (4)	0.008 (4)	0.014 (3)	0.001 (4)
C12	0.11 (1)	0.035 (7)	0.32 (3)	−0.005 (8)	0.06 (2)	−0.03 (1)
C13	0.041 (5)	0.067 (6)	0.046 (5)	0.006 (5)	0.018 (4)	0.003 (5)
C14	0.029 (4)	0.094 (8)	0.044 (5)	−0.003 (5)	0.004 (4)	0.002 (5)
C15	0.037 (4)	0.095 (8)	0.034 (5)	−0.001 (5)	0.002 (4)	0.003 (5)
C16	0.034 (4)	0.060 (6)	0.036 (4)	−0.001 (4)	0.003 (3)	−0.002 (4)
C17	0.031 (4)	0.074 (7)	0.023 (4)	0.002 (4)	0.004 (3)	0.000 (4)
C18	0.039 (5)	0.078 (7)	0.030 (4)	0.004 (5)	0.007 (4)	0.002 (4)
C19	0.045 (5)	0.091 (8)	0.028 (4)	−0.004 (5)	0.012 (4)	0.006 (5)
C20	0.042 (5)	0.077 (7)	0.045 (5)	0.004 (5)	0.020 (4)	0.006 (5)
C21	0.030 (4)	0.071 (6)	0.043 (5)	0.004 (4)	0.015 (4)	0.005 (5)
C22	0.030 (4)	0.063 (6)	0.041 (5)	0.004 (4)	0.008 (4)	0.001 (4)
C23	0.029 (4)	0.084 (7)	0.030 (4)	0.010 (4)	0.002 (3)	−0.004 (4)
C24	0.025 (4)	0.101 (8)	0.043 (5)	0.003 (5)	0.003 (4)	0.005 (5)
C25	0.029 (4)	0.089 (8)	0.047 (5)	0.012 (5)	0.001 (4)	0.006 (5)
C26	0.042 (5)	0.056 (6)	0.039 (5)	0.002 (4)	0.002 (4)	−0.001 (4)
C27	0.045 (5)	0.038 (5)	0.026 (4)	0.001 (4)	−0.003 (3)	−0.006 (4)
C28	0.039 (4)	0.057 (6)	0.030 (4)	0.001 (4)	−0.003 (3)	0.003 (4)
C29	0.053 (6)	0.103 (9)	0.025 (4)	0.006 (5)	0.008 (4)	−0.004 (5)
C30	0.043 (5)	0.13 (1)	0.028 (5)	−0.002 (6)	0.013 (4)	−0.002 (5)
C31	0.033 (4)	0.092 (7)	0.030 (4)	0.004 (5)	0.009 (4)	−0.002 (5)
C32	0.030 (4)	0.076 (7)	0.041 (5)	0.001 (4)	0.016 (4)	−0.002 (5)
C33	0.038 (4)	0.070 (7)	0.027 (4)	0.008 (4)	0.003 (3)	0.003 (4)
C34	0.055 (6)	0.058 (6)	0.044 (5)	0.005 (5)	0.012 (4)	−0.004 (4)
C35	0.045 (5)	0.075 (7)	0.044 (5)	0.014 (5)	0.004 (4)	0.013 (5)
C36	0.055 (6)	0.094 (9)	0.033 (5)	0.012 (6)	0.005 (4)	0.005 (5)
C37	0.067 (6)	0.071 (7)	0.037 (5)	0.008 (5)	0.010 (5)	−0.008 (5)
C38	0.060 (6)	0.060 (6)	0.039 (5)	0.015 (5)	0.008 (4)	−0.001 (4)
C39	0.032 (4)	0.083 (8)	0.040 (5)	0.002 (5)	0.012 (4)	−0.006 (5)
C40	0.069 (7)	0.095 (9)	0.088 (8)	−0.016 (7)	0.043 (6)	−0.030 (7)
C41	0.047 (6)	0.11 (1)	0.087 (8)	−0.025 (6)	0.031 (6)	−0.033 (7)
C42	0.034 (5)	0.095 (9)	0.051 (6)	−0.002 (5)	0.017 (4)	0.004 (5)
C43	0.049 (6)	0.091 (9)	0.054 (6)	0.016 (6)	0.020 (5)	−0.003 (6)
C44	0.048 (5)	0.070 (7)	0.062 (6)	0.004 (5)	0.018 (5)	0.002 (5)
C45	0.041 (5)	0.064 (7)	0.035 (5)	−0.006 (4)	0.003 (4)	−0.004 (4)
C46	0.092 (8)	0.061 (7)	0.049 (6)	−0.012 (6)	0.001 (6)	0.004 (5)
C47	0.092 (8)	0.073 (8)	0.050 (6)	−0.018 (6)	−0.009 (6)	−0.002 (6)
C48	0.054 (6)	0.084 (8)	0.044 (6)	−0.006 (6)	0.000 (5)	−0.011 (6)
C49	0.086 (8)	0.085 (8)	0.037 (6)	−0.007 (7)	0.001 (5)	0.001 (6)
C50	0.069 (7)	0.082 (8)	0.044 (6)	−0.017 (6)	−0.005 (5)	0.002 (6)
C51	0.028 (4)	0.081 (7)	0.038 (4)	−0.003 (5)	0.012 (3)	0.003 (5)
C52	0.047 (6)	0.091 (9)	0.096 (9)	0.017 (6)	0.034 (6)	0.023 (7)
C53	0.058 (7)	0.11 (1)	0.102 (9)	0.021 (7)	0.029 (7)	0.000 (8)
C54	0.035 (5)	0.12 (1)	0.056 (6)	−0.017 (6)	0.012 (4)	−0.003 (7)
C55	0.060 (6)	0.088 (8)	0.057 (6)	−0.012 (6)	0.020 (5)	0.007 (6)
C56	0.050 (6)	0.072 (7)	0.057 (6)	−0.003 (5)	0.023 (5)	0.001 (5)

Geometric parameters (Å, º)

Co1—O6	2.114 (8)	C29—H29	0.949
Co1—N7	1.863 (8)	C30—C31	1.45 (1)
Co1—N8	1.977 (6)	C30—H30	0.950
Co1—N9	1.960 (7)	C31—C32	1.37 (1)
Co1—N10	1.954 (7)	C32—C51	1.51 (1)
Co1—N11	1.975 (7)	C33—C34	1.38 (1)
Cl2—C12	1.73 (2)	C33—C38	1.40 (1)
Cl3—C12	1.74 (2)	C34—C35	1.40 (1)
O4—N7	1.24 (1)	C34—H34	0.951
O5—N7	1.23 (1)	C35—C36	1.37 (1)
O6—H6A	0.947	C35—H35	0.950
O6—H6B	0.963	C36—C37	1.38 (1)
N8—C13	1.39 (1)	C36—H36	0.950
N8—C16	1.374 (10)	C37—C38	1.38 (1)
N9—C18	1.407 (10)	C37—H37	0.949
N9—C21	1.37 (1)	C38—H38	0.951
N10—C23	1.40 (1)	C39—C40	1.38 (2)
N10—C26	1.39 (1)	C39—C44	1.39 (1)
N11—C28	1.396 (9)	C40—C41	1.38 (2)
N11—C31	1.38 (1)	C40—H40	0.950
C12—H12A	0.951	C41—C42	1.36 (2)
C12—H12B	0.948	C41—H41	0.949
C13—C14	1.44 (1)	C42—C43	1.35 (2)
C13—C32	1.37 (1)	C42—H42	0.950
C14—C15	1.33 (1)	C43—C44	1.40 (2)
C14—H14	0.950	C43—H43	0.951
C15—C16	1.44 (1)	C44—H44	0.949
C15—H15	0.950	C45—C46	1.38 (1)
C16—C17	1.37 (1)	C45—C50	1.38 (1)
C17—C18	1.38 (1)	C46—C47	1.38 (1)
C17—C33	1.50 (1)	C46—H46	0.950
C18—C19	1.42 (1)	C47—C48	1.39 (2)
C19—C20	1.32 (1)	C47—H47	0.950
C19—H19	0.950	C48—C49	1.33 (2)
C20—C21	1.43 (1)	C48—H48	0.949
C20—H20	0.950	C49—C50	1.41 (1)
C21—C22	1.39 (1)	C49—H49	0.951
C22—C23	1.37 (1)	C50—H50	0.949
C22—C39	1.50 (1)	C51—C52	1.37 (2)
C23—C24	1.44 (1)	C51—C56	1.37 (1)
C24—C25	1.36 (1)	C52—C53	1.41 (2)
C24—H24	0.950	C52—H52	0.951
C25—C26	1.44 (1)	C53—C54	1.37 (2)
C25—H25	0.950	C53—H53	0.951
C26—C27	1.39 (1)	C54—C55	1.35 (2)
C27—C28	1.36 (1)	C54—H54	0.950
C27—C45	1.49 (1)	C55—C56	1.36 (2)
C28—C29	1.45 (1)	C55—H55	0.949
C29—C30	1.35 (1)	C56—H56	0.949
O4···C34^i	3.28 (1)	O6···C44^iii	3.43 (1)
O4···C35^i	3.48 (1)	O6···C56^iv	3.59 (1)
O4···C15^i	3.48 (1)	N7···C35^i	3.44 (1)
O5···C35^i	3.39 (1)	C30···C37^v	3.59 (1)
O5···C47^ii	3.45 (1)	C31···C35^i	3.56 (1)
O6···C43^iii	3.27 (1)	C32···C35^i	3.59 (1)
O6···C55^iv	3.31 (1)
O6—Co1—N7	178.6 (3)	C27—C28—C29	123.1 (7)
O6—Co1—N8	86.5 (3)	C28—C29—C30	107.9 (7)
O6—Co1—N9	90.0 (3)	C28—C29—H29	126.1
O6—Co1—N10	88.0 (3)	C30—C29—H29	126.0
O6—Co1—N11	87.1 (3)	C29—C30—C31	107.4 (8)
N7—Co1—N8	94.8 (3)	C29—C30—H30	126.3
N7—Co1—N9	89.8 (4)	C31—C30—H30	126.3
N7—Co1—N10	90.6 (3)	N11—C31—C30	109.5 (7)
N7—Co1—N11	93.0 (4)	N11—C31—C32	126.0 (8)
N8—Co1—N9	90.0 (3)	C30—C31—C32	124.4 (8)
N8—Co1—N10	174.5 (3)	C13—C32—C31	122.9 (8)
N8—Co1—N11	89.5 (3)	C13—C32—C51	118.6 (7)
N9—Co1—N10	89.9 (3)	C31—C32—C51	118.3 (8)
N9—Co1—N11	177.1 (3)	C17—C33—C34	121.1 (8)
N10—Co1—N11	90.3 (3)	C17—C33—C38	121.6 (8)
Co1—O6—H6A	120.2	C34—C33—C38	117.2 (7)
Co1—O6—H6B	121.6	C33—C34—C35	121.4 (9)
H6A—O6—H6B	118.1	C33—C34—H34	119.3
Co1—N7—O4	119.9 (6)	C35—C34—H34	119.3
Co1—N7—O5	120.0 (6)	C34—C35—C36	119.8 (9)
O4—N7—O5	120.2 (8)	C34—C35—H35	120.1
Co1—N8—C13	126.9 (5)	C36—C35—H35	120.1
Co1—N8—C16	127.3 (6)	C35—C36—C37	119.9 (8)
C13—N8—C16	105.8 (6)	C35—C36—H36	120.0
Co1—N9—C18	127.1 (6)	C37—C36—H36	120.1
Co1—N9—C21	127.7 (5)	C36—C37—C38	119.5 (9)
C18—N9—C21	104.1 (7)	C36—C37—H37	120.2
Co1—N10—C23	127.9 (5)	C38—C37—H37	120.3
Co1—N10—C26	127.5 (6)	C33—C38—C37	122.0 (9)
C23—N10—C26	104.6 (6)	C33—C38—H38	119.0
Co1—N11—C28	124.8 (6)	C37—C38—H38	119.0
Co1—N11—C31	127.8 (5)	C22—C39—C40	120.4 (9)
C28—N11—C31	106.8 (7)	C22—C39—C44	121.1 (9)
Cl2—C12—Cl3	111.2 (7)	C40—C39—C44	118.4 (9)
Cl2—C12—H12A	108.9	C39—C40—C41	121 (1)
Cl2—C12—H12B	109.1	C39—C40—H40	119.3
Cl3—C12—H12A	109.0	C41—C40—H40	119.2
Cl3—C12—H12B	109.1	C40—C41—C42	119 (1)
H12A—C12—H12B	109.6	C40—C41—H41	120.1
N8—C13—C14	109.0 (7)	C42—C41—H41	120.1
N8—C13—C32	126.3 (7)	C41—C42—C43	119.6 (10)
C14—C13—C32	124.5 (8)	C41—C42—H42	120.2
C13—C14—C15	107.8 (8)	C43—C42—H42	120.2
C13—C14—H14	126.1	C42—C43—C44	121 (1)
C15—C14—H14	126.1	C42—C43—H43	119.2
C14—C15—C16	107.7 (7)	C44—C43—H43	119.1
C14—C15—H15	126.2	C39—C44—C43	118.7 (9)
C16—C15—H15	126.2	C39—C44—H44	120.6
N8—C16—C15	109.6 (7)	C43—C44—H44	120.7
N8—C16—C17	125.8 (7)	C27—C45—C46	120.3 (8)
C15—C16—C17	124.5 (7)	C27—C45—C50	121.0 (8)
C16—C17—C18	124.2 (7)	C46—C45—C50	118.7 (8)
C16—C17—C33	118.4 (7)	C45—C46—C47	121.7 (10)
C18—C17—C33	117.2 (7)	C45—C46—H46	119.1
N9—C18—C17	124.1 (8)	C47—C46—H46	119.2
N9—C18—C19	109.7 (7)	C46—C47—C48	119 (1)
C17—C18—C19	126.1 (7)	C46—C47—H47	120.4
C18—C19—C20	107.8 (7)	C48—C47—H47	120.4
C18—C19—H19	126.1	C47—C48—C49	119.5 (9)
C20—C19—H19	126.1	C47—C48—H48	120.3
C19—C20—C21	107.6 (8)	C49—C48—H48	120.2
C19—C20—H20	126.2	C48—C49—C50	122 (1)
C21—C20—H20	126.2	C48—C49—H49	119.0
N9—C21—C20	110.7 (7)	C50—C49—H49	118.9
N9—C21—C22	125.4 (8)	C45—C50—C49	118 (1)
C20—C21—C22	123.9 (8)	C45—C50—H50	120.8
C21—C22—C23	123.3 (8)	C49—C50—H50	120.7
C21—C22—C39	117.8 (8)	C32—C51—C52	121.2 (9)
C23—C22—C39	118.7 (7)	C32—C51—C56	120.2 (9)
N10—C23—C22	124.8 (7)	C52—C51—C56	118.6 (9)
N10—C23—C24	110.6 (7)	C51—C52—C53	118 (1)
C22—C23—C24	124.5 (8)	C51—C52—H52	120.7
C23—C24—C25	106.6 (8)	C53—C52—H52	120.7
C23—C24—H24	126.7	C52—C53—C54	120 (1)
C25—C24—H24	126.7	C52—C53—H53	119.7
C24—C25—C26	107.6 (7)	C54—C53—H53	119.8
C24—C25—H25	126.2	C53—C54—C55	119 (1)
C26—C25—H25	126.2	C53—C54—H54	120.0
N10—C26—C25	110.4 (8)	C55—C54—H54	120.0
N10—C26—C27	126.4 (7)	C54—C55—C56	119 (1)
C25—C26—C27	123.2 (7)	C54—C55—H55	120.1
C26—C27—C28	121.0 (7)	C56—C55—H55	120.2
C26—C27—C45	119.1 (7)	C51—C56—C55	122.5 (10)
C28—C27—C45	119.8 (8)	C51—C56—H56	118.8
N11—C28—C27	128.4 (8)	C55—C56—H56	118.7
N11—C28—C29	108.3 (7)

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