Dichlorido[(4E,11E)-5,7,12,14-tetra-benzyl-7,14-dimethyl-1,4,8,11-tetra-aza-cyclo-tetra-deca-4,11-diene]cobalt(III) perchlorate.

The Co(III) atom in the title complex, [CoCl(2)(C(40)H(48)N(4))]ClO(4), is octa-hedrally coordinated within a trans-Cl(2)N(4) donor set provided by the tetra-dentate macrocylic ligand and two chloride ions. The N-H atoms, which are orientated to one side of the N(4) plane, form hydrogen bonds with chloride ions and perchlorate-O atoms. These along with C-H⋯O inter-actions consolidate the three-dimensional crystal structure. One of the benzene rings was disordered. This was resolved over two positions with the major component of the disorder having a site-occupancy factor of 0.672 (4).

Related literature

For background to the synthesis, characterization, kinetic studies and biological activity of 14-membered methyl-substituted tetra­aza­macrocyclic ligands, their N-substituted derivatives and metal complexes, see: Bembi et al. (1990 ▶); Roy et al. (2007 ▶, 2011a ▶); Hazari et al. (2008 ▶). For a related structure, see: Roy et al. (2011b ▶).

Experimental

Crystal data

[CoCl2(C40H48N4)]ClO4

M = 814.10

Triclinic,

a = 10.8111 (7) Å

b = 13.835 (2) Å

c = 14.868 (3) Å

α = 73.66 (3)°

β = 70.06 (3)°

γ = 68.65 (2)°

V = 1915.6 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.70 mm−1

T = 153 K

0.30 × 0.20 × 0.10 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.627, T max = 1.000

20336 measured reflections

7470 independent reflections

6940 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.142

S = 1.05

7470 reflections

476 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.72 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) & DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046484/pv2479sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046484/pv2479Isup2.hkl

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

[CoCl2(C40H48N4)]ClO4	Z = 2
Mr = 814.10	F(000) = 852
Triclinic, P1	Dx = 1.411 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.8111 (7) Å	Cell parameters from 6113 reflections
b = 13.835 (2) Å	θ = 2.2–30.4°
c = 14.868 (3) Å	µ = 0.70 mm−1
α = 73.66 (3)°	T = 153 K
β = 70.06 (3)°	Prism, green
γ = 68.65 (2)°	0.30 × 0.20 × 0.10 mm
V = 1915.6 (5) Å3

Rigaku AFC12K/SATURN724 diffractometer	7470 independent reflections
Radiation source: fine-focus sealed tube	6940 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
Tmin = 0.627, Tmax = 1.000	k = −15→17
20336 measured reflections	l = −18→18

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0779P)2 + 2.2391P] where P = (Fo2 + 2Fc2)/3
7470 reflections	(Δ/σ)max = 0.001
476 parameters	Δρmax = 0.72 e Å−3
2 restraints	Δρmin = −0.50 e Å−3

Experimental. Microanalysis: Calculated for C40H48Cl3CoN4O4, C, 59.09; H, 5.78; N, 6.89; Co, 7.25%. Found, C, 59.25; H, 5.65; N, 6.89; Co, 7.05%. IR (cm-1): 3161 ν(N—H); 3024 ν(Ar—H); 2949 and 2978 ν(C—H); 1393 ν(CH3); 1095 and 622 ν(ClO4-); 550 ν(Co—N).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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)
Co	0.03217 (3)	0.25958 (2)	0.57912 (2)	0.01928 (12)
Cl1	−0.08339 (7)	0.13989 (5)	0.64106 (5)	0.02986 (17)
Cl2	0.14748 (6)	0.38188 (5)	0.51694 (4)	0.02299 (15)
N1	−0.0314 (2)	0.29843 (17)	0.46384 (16)	0.0230 (4)
N2	0.2055 (2)	0.15227 (16)	0.52957 (15)	0.0219 (4)
H2N	0.265 (2)	0.186 (2)	0.518 (2)	0.026*
N3	0.0985 (2)	0.22239 (16)	0.69411 (16)	0.0227 (4)
N4	−0.1336 (2)	0.37339 (17)	0.62547 (15)	0.0217 (4)
H4N	−0.105 (3)	0.4285 (16)	0.5924 (19)	0.026*
C1	0.0414 (3)	0.2780 (2)	0.3799 (2)	0.0272 (6)
C2	0.1919 (3)	0.2166 (2)	0.36292 (19)	0.0263 (5)
H2A	0.2430	0.2636	0.3621	0.032*
H2B	0.2250	0.1975	0.2976	0.032*
C3	0.2289 (3)	0.1159 (2)	0.43667 (19)	0.0235 (5)
C4	0.2349 (3)	0.0693 (2)	0.61436 (19)	0.0268 (6)
H4A	0.3298	0.0215	0.5966	0.032*
H4B	0.1696	0.0271	0.6367	0.032*
C5	0.2186 (3)	0.1249 (2)	0.69361 (19)	0.0269 (6)
H5A	0.2038	0.0775	0.7575	0.032*
H5B	0.3034	0.1438	0.6821	0.032*
C6	0.0646 (3)	0.2809 (2)	0.75664 (19)	0.0248 (5)
C7	−0.0518 (3)	0.3823 (2)	0.75592 (19)	0.0258 (5)
H7A	−0.0141	0.4381	0.7091	0.031*
H7B	−0.0823	0.4014	0.8211	0.031*
C8	−0.1801 (3)	0.3860 (2)	0.73077 (19)	0.0264 (6)
C9	−0.2421 (3)	0.3776 (2)	0.5824 (2)	0.0279 (6)
H9A	−0.3176	0.4446	0.5888	0.033*
H9B	−0.2811	0.3183	0.6163	0.033*
C10	−0.1742 (3)	0.3700 (2)	0.4760 (2)	0.0261 (5)
H10A	−0.2277	0.3430	0.4518	0.031*
H10B	−0.1729	0.4410	0.4375	0.031*
C11	−0.0180 (3)	0.3201 (3)	0.2918 (2)	0.0397 (7)
H11A	−0.1191	0.3332	0.3150	0.048*
H11B	−0.0006	0.3886	0.2589	0.048*
C12	0.0400 (3)	0.2479 (2)	0.2186 (2)	0.0331 (6)
C13	0.1397 (4)	0.2649 (3)	0.1340 (2)	0.0432 (8)
H13	0.1690	0.3257	0.1200	0.052*
C14	0.1982 (4)	0.1960 (3)	0.0691 (2)	0.0521 (9)
H14	0.2669	0.2094	0.0112	0.063*
C15	0.1565 (5)	0.1085 (3)	0.0888 (3)	0.0630 (12)
H15	0.1967	0.0604	0.0447	0.076*
C16	0.0565 (6)	0.0897 (3)	0.1725 (3)	0.0714 (13)
H16	0.0278	0.0287	0.1860	0.086*
C17	−0.0029 (4)	0.1600 (3)	0.2374 (2)	0.0534 (9)
H17	−0.0729	0.1473	0.2947	0.064*
C18	0.1422 (3)	0.0454 (2)	0.4501 (2)	0.0305 (6)
H18A	0.1701	−0.0196	0.4958	0.046*
H18B	0.1556	0.0280	0.3873	0.046*
H18C	0.0447	0.0824	0.4758	0.046*
C19	0.3844 (3)	0.0560 (2)	0.4032 (2)	0.0274 (6)
H19A	0.4384	0.1015	0.4010	0.033*
H19B	0.4063	−0.0079	0.4528	0.033*
C20	0.4313 (3)	0.0230 (2)	0.3052 (2)	0.0281 (6)
C21	0.4946 (3)	0.0826 (3)	0.2235 (2)	0.0398 (7)
H21	0.5067	0.1452	0.2289	0.048*
C22	0.5411 (4)	0.0521 (3)	0.1329 (3)	0.0528 (9)
H22	0.5844	0.0938	0.0771	0.063*
C23	0.5241 (4)	−0.0387 (3)	0.1248 (3)	0.0519 (10)
H23	0.5557	−0.0598	0.0633	0.062*
C24	0.4615 (3)	−0.0988 (3)	0.2055 (3)	0.0451 (8)
H24	0.4493	−0.1611	0.1995	0.054*
C25	0.4161 (3)	−0.0692 (2)	0.2956 (2)	0.0349 (6)
H25	0.3743	−0.1119	0.3512	0.042*
C26	0.1434 (3)	0.2615 (2)	0.8307 (2)	0.0298 (6)
H26A	0.0801	0.2578	0.8971	0.036*
H26B	0.2173	0.1933	0.8275	0.036*
C27	0.2058 (3)	0.3502 (2)	0.8096 (2)	0.0291 (6)
C28	0.1666 (3)	0.4162 (2)	0.8764 (2)	0.0355 (7)
H28	0.0996	0.4058	0.9364	0.043*
C29	0.2248 (4)	0.4971 (3)	0.8560 (3)	0.0450 (8)
H29	0.1979	0.5414	0.9022	0.054*
C30	0.3218 (3)	0.5132 (3)	0.7689 (3)	0.0441 (8)
H30	0.3616	0.5683	0.7552	0.053*
C31	0.3605 (3)	0.4491 (3)	0.7019 (3)	0.0388 (7)
H31	0.4265	0.4607	0.6417	0.047*
C32	0.3035 (3)	0.3676 (2)	0.7217 (2)	0.0340 (6)
H32	0.3312	0.3235	0.6752	0.041*
C33	−0.2828 (3)	0.4958 (2)	0.7397 (2)	0.0336 (6)
H33A	−0.3678	0.4998	0.7268	0.050*
H33B	−0.2427	0.5491	0.6924	0.050*
H33C	−0.3038	0.5088	0.8055	0.050*
Cl3	0.54134 (7)	0.26751 (5)	0.43796 (5)	0.03305 (18)
O1	0.4658 (2)	0.20304 (16)	0.51435 (16)	0.0382 (5)
O2	0.5109 (3)	0.36627 (18)	0.4651 (2)	0.0499 (6)
O3	0.6847 (2)	0.2140 (2)	0.4224 (2)	0.0592 (7)
O4	0.4999 (3)	0.2853 (2)	0.35077 (18)	0.0575 (7)
C34A	−0.2460 (18)	0.2928 (8)	0.8000 (11)	0.0270 (17)	0.672 (3)
H34A	−0.3205	0.2923	0.7758	0.032*	0.672 (3)
H34B	−0.1740	0.2238	0.7954	0.032*	0.672 (3)
C35A	−0.3028 (3)	0.3053 (3)	0.90364 (18)	0.0331 (9)	0.672 (3)
C36A	−0.4428 (3)	0.3556 (3)	0.9363 (2)	0.0439 (11)	0.672 (3)
H36A	−0.4986	0.3835	0.8922	0.053*	0.672 (3)
C37A	−0.5011 (3)	0.3649 (3)	1.0337 (2)	0.0550 (13)	0.672 (3)
H37A	−0.5968	0.3993	1.0560	0.066*	0.672 (3)
C38A	−0.4194 (4)	0.3240 (3)	1.09829 (16)	0.0597 (16)	0.672 (3)
H38A	−0.4593	0.3304	1.1648	0.072*	0.672 (3)
C39A	−0.2795 (4)	0.2738 (3)	1.0656 (2)	0.0600 (16)	0.672 (3)
H39A	−0.2236	0.2458	1.1098	0.072*	0.672 (3)
C40A	−0.2212 (3)	0.2644 (3)	0.9683 (2)	0.0477 (13)	0.672 (3)
H40A	−0.1255	0.2300	0.9459	0.057*	0.672 (3)
C34B	−0.245 (4)	0.314 (2)	0.789 (3)	0.0270 (17)	0.328 (3)
H34C	−0.3364	0.3354	0.7759	0.032*	0.328 (3)
H34D	−0.1923	0.2458	0.7662	0.032*	0.328 (3)
C35B	−0.2705 (8)	0.2912 (6)	0.9041 (4)	0.0331 (9)	0.328 (3)
C36B	−0.3766 (7)	0.3593 (5)	0.9616 (5)	0.0439 (11)	0.328 (3)
H36B	−0.4417	0.4163	0.9335	0.053*	0.328 (3)
C37B	−0.3876 (8)	0.3441 (6)	1.0601 (5)	0.0550 (13)	0.328 (3)
H37B	−0.4601	0.3907	1.0994	0.066*	0.328 (3)
C38B	−0.2923 (10)	0.2607 (7)	1.1012 (4)	0.0597 (16)	0.328 (3)
H38B	−0.2998	0.2503	1.1686	0.07 (4)*	0.328 (3)
C39B	−0.1861 (8)	0.1926 (6)	1.0438 (5)	0.0600 (16)	0.328 (3)
H39B	−0.1210	0.1356	1.0719	0.072*	0.328 (3)
C40B	−0.1752 (7)	0.2078 (6)	0.9452 (5)	0.0477 (13)	0.328 (3)
H40B	−0.1027	0.1613	0.9060	0.057*	0.328 (3)

	U11	U22	U33	U12	U13	U23
Co	0.01748 (19)	0.0189 (2)	0.02131 (19)	−0.00528 (14)	−0.00556 (14)	−0.00311 (13)
Cl1	0.0289 (3)	0.0277 (3)	0.0344 (4)	−0.0131 (3)	−0.0044 (3)	−0.0063 (3)
Cl2	0.0211 (3)	0.0206 (3)	0.0262 (3)	−0.0075 (2)	−0.0044 (2)	−0.0033 (2)
N1	0.0188 (10)	0.0235 (11)	0.0259 (11)	−0.0040 (8)	−0.0070 (9)	−0.0053 (9)
N2	0.0227 (11)	0.0197 (10)	0.0241 (11)	−0.0051 (8)	−0.0084 (9)	−0.0041 (8)
N3	0.0197 (10)	0.0214 (11)	0.0266 (11)	−0.0068 (8)	−0.0066 (9)	−0.0022 (8)
N4	0.0195 (10)	0.0238 (11)	0.0209 (10)	−0.0072 (8)	−0.0039 (8)	−0.0034 (8)
C1	0.0277 (14)	0.0248 (13)	0.0302 (14)	−0.0046 (10)	−0.0121 (11)	−0.0055 (11)
C2	0.0238 (13)	0.0283 (14)	0.0251 (13)	−0.0045 (10)	−0.0056 (11)	−0.0075 (11)
C3	0.0206 (12)	0.0228 (13)	0.0286 (13)	−0.0025 (10)	−0.0090 (11)	−0.0093 (10)
C4	0.0270 (13)	0.0225 (13)	0.0273 (13)	−0.0023 (10)	−0.0099 (11)	−0.0023 (10)
C5	0.0255 (13)	0.0254 (13)	0.0267 (13)	−0.0023 (10)	−0.0106 (11)	−0.0026 (10)
C6	0.0247 (13)	0.0274 (13)	0.0236 (12)	−0.0118 (10)	−0.0064 (10)	−0.0012 (10)
C7	0.0289 (14)	0.0254 (13)	0.0229 (12)	−0.0085 (11)	−0.0045 (11)	−0.0063 (10)
C8	0.0247 (13)	0.0288 (14)	0.0233 (13)	−0.0063 (11)	−0.0034 (11)	−0.0071 (10)
C9	0.0175 (12)	0.0323 (14)	0.0323 (14)	−0.0053 (10)	−0.0062 (11)	−0.0064 (11)
C10	0.0202 (13)	0.0262 (13)	0.0317 (14)	−0.0016 (10)	−0.0110 (11)	−0.0071 (11)
C11	0.0395 (17)	0.0425 (17)	0.0331 (16)	0.0050 (13)	−0.0184 (14)	−0.0131 (13)
C12	0.0319 (15)	0.0384 (16)	0.0264 (14)	−0.0027 (12)	−0.0128 (12)	−0.0058 (12)
C13	0.0477 (19)	0.0477 (19)	0.0307 (16)	−0.0109 (15)	−0.0127 (14)	−0.0036 (14)
C14	0.054 (2)	0.058 (2)	0.0284 (16)	−0.0016 (17)	−0.0061 (15)	−0.0110 (15)
C15	0.093 (3)	0.047 (2)	0.039 (2)	0.000 (2)	−0.023 (2)	−0.0148 (17)
C16	0.125 (4)	0.056 (3)	0.048 (2)	−0.045 (3)	−0.026 (3)	−0.0022 (19)
C17	0.070 (3)	0.070 (3)	0.0291 (16)	−0.036 (2)	−0.0096 (17)	−0.0064 (16)
C18	0.0267 (14)	0.0287 (14)	0.0398 (15)	−0.0083 (11)	−0.0094 (12)	−0.0109 (12)
C19	0.0214 (13)	0.0280 (14)	0.0320 (14)	−0.0033 (10)	−0.0078 (11)	−0.0087 (11)
C20	0.0196 (12)	0.0307 (14)	0.0306 (14)	0.0020 (10)	−0.0076 (11)	−0.0118 (11)
C21	0.0331 (16)	0.0392 (17)	0.0391 (17)	−0.0060 (13)	−0.0028 (13)	−0.0097 (13)
C22	0.045 (2)	0.057 (2)	0.0339 (17)	−0.0023 (16)	0.0015 (15)	−0.0065 (16)
C23	0.046 (2)	0.064 (2)	0.0354 (17)	0.0091 (17)	−0.0118 (15)	−0.0256 (17)
C24	0.0412 (18)	0.0457 (19)	0.050 (2)	0.0034 (15)	−0.0164 (16)	−0.0280 (16)
C25	0.0323 (15)	0.0325 (15)	0.0393 (16)	−0.0025 (12)	−0.0100 (13)	−0.0144 (13)
C26	0.0348 (15)	0.0318 (14)	0.0255 (13)	−0.0103 (12)	−0.0115 (12)	−0.0044 (11)
C27	0.0285 (14)	0.0307 (14)	0.0303 (14)	−0.0081 (11)	−0.0144 (12)	−0.0018 (11)
C28	0.0411 (17)	0.0379 (16)	0.0324 (15)	−0.0121 (13)	−0.0155 (13)	−0.0061 (12)
C29	0.057 (2)	0.0374 (17)	0.054 (2)	−0.0145 (15)	−0.0316 (18)	−0.0073 (15)
C30	0.0443 (18)	0.0365 (17)	0.063 (2)	−0.0184 (14)	−0.0333 (17)	0.0064 (15)
C31	0.0281 (15)	0.0401 (17)	0.0474 (18)	−0.0133 (13)	−0.0167 (14)	0.0059 (14)
C32	0.0292 (15)	0.0380 (16)	0.0352 (15)	−0.0082 (12)	−0.0139 (12)	−0.0027 (12)
C33	0.0285 (14)	0.0323 (15)	0.0311 (14)	−0.0018 (11)	−0.0012 (12)	−0.0103 (12)
Cl3	0.0299 (4)	0.0291 (4)	0.0425 (4)	−0.0119 (3)	−0.0124 (3)	−0.0022 (3)
O1	0.0405 (12)	0.0344 (11)	0.0437 (12)	−0.0187 (9)	−0.0179 (10)	0.0050 (9)
O2	0.0455 (13)	0.0350 (12)	0.0713 (17)	−0.0174 (10)	−0.0075 (12)	−0.0154 (11)
O3	0.0303 (12)	0.0483 (15)	0.093 (2)	−0.0083 (11)	−0.0085 (13)	−0.0182 (14)
O4	0.0720 (18)	0.0681 (17)	0.0413 (14)	−0.0345 (14)	−0.0223 (13)	0.0043 (12)
C34A	0.0324 (16)	0.021 (5)	0.023 (4)	−0.018 (4)	0.001 (2)	0.005 (4)
C35A	0.038 (3)	0.0297 (19)	0.0295 (15)	−0.0150 (18)	−0.0039 (16)	−0.0024 (13)
C36A	0.041 (3)	0.046 (2)	0.033 (2)	−0.011 (2)	0.0013 (19)	−0.0047 (19)
C37A	0.061 (3)	0.051 (3)	0.035 (2)	−0.015 (3)	0.011 (2)	−0.012 (2)
C38A	0.097 (5)	0.060 (4)	0.029 (2)	−0.051 (3)	0.002 (3)	−0.005 (2)
C39A	0.079 (4)	0.082 (4)	0.037 (3)	−0.054 (3)	−0.022 (3)	0.011 (3)
C40A	0.042 (3)	0.053 (3)	0.043 (3)	−0.023 (3)	−0.010 (2)	0.010 (2)
C34B	0.0324 (16)	0.021 (5)	0.023 (4)	−0.018 (4)	0.001 (2)	0.005 (4)
C35B	0.038 (3)	0.0297 (19)	0.0295 (15)	−0.0150 (18)	−0.0039 (16)	−0.0024 (13)
C36B	0.041 (3)	0.046 (2)	0.033 (2)	−0.011 (2)	0.0013 (19)	−0.0047 (19)
C37B	0.061 (3)	0.051 (3)	0.035 (2)	−0.015 (3)	0.011 (2)	−0.012 (2)
C38B	0.097 (5)	0.060 (4)	0.029 (2)	−0.051 (3)	0.002 (3)	−0.005 (2)
C39B	0.079 (4)	0.082 (4)	0.037 (3)	−0.054 (3)	−0.022 (3)	0.011 (3)
C40B	0.042 (3)	0.053 (3)	0.043 (3)	−0.023 (3)	−0.010 (2)	0.010 (2)

Co—N1	1.927 (2)	C20—C21	1.381 (4)
Co—N3	1.943 (2)	C20—C25	1.394 (4)
Co—N4	1.969 (2)	C21—C22	1.396 (5)
Co—N2	1.977 (2)	C21—H21	0.9500
Co—Cl1	2.2395 (9)	C22—C23	1.377 (6)
Co—Cl2	2.2676 (8)	C22—H22	0.9500
N1—C1	1.274 (4)	C23—C24	1.373 (5)
N1—C10	1.482 (3)	C23—H23	0.9500
N2—C4	1.484 (3)	C24—C25	1.384 (4)
N2—C3	1.511 (3)	C24—H24	0.9500
N2—H2N	0.877 (10)	C25—H25	0.9500
N3—C6	1.276 (3)	C26—C27	1.519 (4)
N3—C5	1.493 (3)	C26—H26A	0.9900
N4—C9	1.494 (3)	C26—H26B	0.9900
N4—C8	1.512 (3)	C27—C28	1.393 (4)
N4—H4N	0.878 (10)	C27—C32	1.396 (4)
C1—C2	1.506 (4)	C28—C29	1.390 (5)
C1—C11	1.530 (4)	C28—H28	0.9500
C2—C3	1.529 (4)	C29—C30	1.381 (5)
C2—H2A	0.9900	C29—H29	0.9500
C2—H2B	0.9900	C30—C31	1.377 (5)
C3—C18	1.517 (4)	C30—H30	0.9500
C3—C19	1.552 (3)	C31—C32	1.390 (4)
C4—C5	1.511 (4)	C31—H31	0.9500
C4—H4A	0.9900	C32—H32	0.9500
C4—H4B	0.9900	C33—H33A	0.9800
C5—H5A	0.9900	C33—H33B	0.9800
C5—H5B	0.9900	C33—H33C	0.9800
C6—C7	1.506 (4)	Cl3—O3	1.421 (2)
C6—C26	1.522 (4)	Cl3—O2	1.425 (2)
C7—C8	1.535 (4)	Cl3—O4	1.441 (3)
C7—H7A	0.9900	Cl3—O1	1.442 (2)
C7—H7B	0.9900	C34A—C35A	1.486 (17)
C8—C33	1.531 (4)	C34A—H34A	0.9900
C8—C34B	1.36 (3)	C34A—H34B	0.9900
C8—C34A	1.629 (10)	C35A—C36A	1.3900
C9—C10	1.515 (4)	C35A—C40A	1.3900
C9—H9A	0.9900	C36A—C37A	1.3900
C9—H9B	0.9900	C36A—H36A	0.9500
C10—H10A	0.9900	C37A—C38A	1.3900
C10—H10B	0.9900	C37A—H37A	0.9500
C11—C12	1.505 (4)	C38A—C39A	1.3900
C11—H11A	0.9900	C38A—H38A	0.9500
C11—H11B	0.9900	C39A—C40A	1.3900
C12—C13	1.375 (4)	C39A—H39A	0.9500
C12—C17	1.379 (5)	C40A—H40A	0.9500
C13—C14	1.380 (5)	C34B—C35B	1.60 (4)
C13—H13	0.9500	C34B—H34C	0.9900
C14—C15	1.365 (6)	C34B—H34D	0.9900
C14—H14	0.9500	C35B—C36B	1.3900
C15—C16	1.374 (6)	C35B—C40B	1.3900
C15—H15	0.9500	C36B—C37B	1.3900
C16—C17	1.393 (6)	C36B—H36B	0.9500
C16—H16	0.9500	C37B—C38B	1.3900
C17—H17	0.9500	C37B—H37B	0.9500
C18—H18A	0.9800	C38B—C39B	1.3900
C18—H18B	0.9800	C38B—H38B	0.9500
C18—H18C	0.9800	C39B—C40B	1.3900
C19—C20	1.514 (4)	C39B—H39B	0.9500
C19—H19A	0.9900	C40B—H40B	0.9500
C19—H19B	0.9900
N1—Co—N3	178.83 (9)	C3—C18—H18A	109.5
N1—Co—N4	84.22 (9)	C3—C18—H18B	109.5
N3—Co—N4	95.83 (9)	H18A—C18—H18B	109.5
N1—Co—N2	96.07 (9)	C3—C18—H18C	109.5
N3—Co—N2	83.80 (9)	H18A—C18—H18C	109.5
N4—Co—N2	176.17 (9)	H18B—C18—H18C	109.5
N1—Co—Cl1	89.85 (7)	C20—C19—C3	115.3 (2)
N3—Co—Cl1	91.32 (7)	C20—C19—H19A	108.4
N4—Co—Cl1	91.81 (7)	C3—C19—H19A	108.4
N2—Co—Cl1	92.00 (7)	C20—C19—H19B	108.4
N1—Co—Cl2	90.11 (7)	C3—C19—H19B	108.4
N3—Co—Cl2	88.72 (7)	H19A—C19—H19B	107.5
N4—Co—Cl2	87.68 (7)	C21—C20—C25	118.6 (3)
N2—Co—Cl2	88.50 (7)	C21—C20—C19	120.0 (3)
Cl1—Co—Cl2	179.50 (3)	C25—C20—C19	121.3 (3)
C1—N1—C10	119.7 (2)	C20—C21—C22	120.8 (3)
C1—N1—Co	126.26 (18)	C20—C21—H21	119.6
C10—N1—Co	113.59 (17)	C22—C21—H21	119.6
C4—N2—C3	117.1 (2)	C23—C22—C21	119.7 (3)
C4—N2—Co	106.90 (16)	C23—C22—H22	120.2
C3—N2—Co	119.99 (15)	C21—C22—H22	120.2
C4—N2—H2N	103 (2)	C24—C23—C22	120.0 (3)
C3—N2—H2N	107 (2)	C24—C23—H23	120.0
Co—N2—H2N	100 (2)	C22—C23—H23	120.0
C6—N3—C5	120.0 (2)	C23—C24—C25	120.4 (3)
C6—N3—Co	126.05 (18)	C23—C24—H24	119.8
C5—N3—Co	112.83 (16)	C25—C24—H24	119.8
C9—N4—C8	116.6 (2)	C24—C25—C20	120.4 (3)
C9—N4—Co	107.52 (16)	C24—C25—H25	119.8
C8—N4—Co	120.35 (16)	C20—C25—H25	119.8
C9—N4—H4N	105 (2)	C27—C26—C6	109.7 (2)
C8—N4—H4N	105 (2)	C27—C26—H26A	109.7
Co—N4—H4N	100 (2)	C6—C26—H26A	109.7
N1—C1—C2	120.8 (2)	C27—C26—H26B	109.7
N1—C1—C11	121.6 (2)	C6—C26—H26B	109.7
C2—C1—C11	117.5 (2)	H26A—C26—H26B	108.2
C1—C2—C3	116.3 (2)	C28—C27—C32	118.8 (3)
C1—C2—H2A	108.2	C28—C27—C26	121.1 (3)
C3—C2—H2A	108.2	C32—C27—C26	120.1 (3)
C1—C2—H2B	108.2	C29—C28—C27	120.4 (3)
C3—C2—H2B	108.2	C29—C28—H28	119.8
H2A—C2—H2B	107.4	C27—C28—H28	119.8
N2—C3—C18	112.3 (2)	C30—C29—C28	120.2 (3)
N2—C3—C2	105.6 (2)	C30—C29—H29	119.9
C18—C3—C2	111.0 (2)	C28—C29—H29	119.9
N2—C3—C19	107.4 (2)	C31—C30—C29	119.9 (3)
C18—C3—C19	110.3 (2)	C31—C30—H30	120.0
C2—C3—C19	109.9 (2)	C29—C30—H30	120.0
N2—C4—C5	106.9 (2)	C30—C31—C32	120.4 (3)
N2—C4—H4A	110.3	C30—C31—H31	119.8
C5—C4—H4A	110.3	C32—C31—H31	119.8
N2—C4—H4B	110.3	C31—C32—C27	120.3 (3)
C5—C4—H4B	110.3	C31—C32—H32	119.9
H4A—C4—H4B	108.6	C27—C32—H32	119.9
N3—C5—C4	109.4 (2)	C8—C33—H33A	109.5
N3—C5—H5A	109.8	C8—C33—H33B	109.5
C4—C5—H5A	109.8	H33A—C33—H33B	109.5
N3—C5—H5B	109.8	C8—C33—H33C	109.5
C4—C5—H5B	109.8	H33A—C33—H33C	109.5
H5A—C5—H5B	108.2	H33B—C33—H33C	109.5
N3—C6—C7	121.2 (2)	O3—Cl3—O2	109.85 (16)
N3—C6—C26	124.3 (2)	O3—Cl3—O4	110.38 (19)
C7—C6—C26	114.3 (2)	O2—Cl3—O4	109.29 (17)
C6—C7—C8	118.6 (2)	O3—Cl3—O1	108.94 (15)
C6—C7—H7A	107.7	O2—Cl3—O1	109.77 (15)
C8—C7—H7A	107.7	O4—Cl3—O1	108.59 (14)
C6—C7—H7B	107.7	C35A—C34A—C8	113.0 (10)
C8—C7—H7B	107.7	C35A—C34A—H34A	109.0
H7A—C7—H7B	107.1	C8—C34A—H34A	109.0
N4—C8—C33	108.7 (2)	C35A—C34A—H34B	109.0
N4—C8—C7	106.2 (2)	C8—C34A—H34B	109.0
C33—C8—C7	107.4 (2)	H34A—C34A—H34B	107.8
N4—C8—C34B	111.2 (18)	C36A—C35A—C40A	120.0
C33—C8—C34B	107.7 (16)	C36A—C35A—C34A	118.2 (7)
C7—C8—C34B	115.3 (17)	C40A—C35A—C34A	121.8 (7)
N4—C8—C34A	110.5 (7)	C35A—C36A—C37A	120.0
C33—C8—C34A	112.0 (6)	C35A—C36A—H36A	120.0
C7—C8—C34A	111.8 (6)	C37A—C36A—H36A	120.0
N4—C9—C10	107.3 (2)	C38A—C37A—C36A	120.0
N4—C9—H9A	110.3	C38A—C37A—H37A	120.0
C10—C9—H9A	110.3	C36A—C37A—H37A	120.0
N4—C9—H9B	110.3	C37A—C38A—C39A	120.0
C10—C9—H9B	110.3	C37A—C38A—H38A	120.0
H9A—C9—H9B	108.5	C39A—C38A—H38A	120.0
N1—C10—C9	110.0 (2)	C38A—C39A—C40A	120.0
N1—C10—H10A	109.7	C38A—C39A—H39A	120.0
C9—C10—H10A	109.7	C40A—C39A—H39A	120.0
N1—C10—H10B	109.7	C39A—C40A—C35A	120.0
C9—C10—H10B	109.7	C39A—C40A—H40A	120.0
H10A—C10—H10B	108.2	C35A—C40A—H40A	120.0
C12—C11—C1	114.6 (2)	C35B—C34B—C8	121 (3)
C12—C11—H11A	108.6	C35B—C34B—H34C	107.1
C1—C11—H11A	108.6	C8—C34B—H34C	107.1
C12—C11—H11B	108.6	C35B—C34B—H34D	107.1
C1—C11—H11B	108.6	C8—C34B—H34D	107.1
H11A—C11—H11B	107.6	H34C—C34B—H34D	106.8
C13—C12—C17	118.5 (3)	C36B—C35B—C40B	120.0
C13—C12—C11	121.5 (3)	C36B—C35B—C34B	121.1 (14)
C17—C12—C11	119.9 (3)	C40B—C35B—C34B	118.5 (14)
C12—C13—C14	121.7 (4)	C37B—C36B—C35B	120.0
C12—C13—H13	119.1	C37B—C36B—H36B	120.0
C14—C13—H13	119.1	C35B—C36B—H36B	120.0
C15—C14—C13	119.4 (4)	C36B—C37B—C38B	120.0
C15—C14—H14	120.3	C36B—C37B—H37B	120.0
C13—C14—H14	120.3	C38B—C37B—H37B	120.0
C14—C15—C16	120.1 (4)	C39B—C38B—C37B	120.0
C14—C15—H15	119.9	C39B—C38B—H38B	120.0
C16—C15—H15	119.9	C37B—C38B—H38B	120.0
C15—C16—C17	120.2 (4)	C38B—C39B—C40B	120.0
C15—C16—H16	119.9	C38B—C39B—H39B	120.0
C17—C16—H16	119.9	C40B—C39B—H39B	120.0
C12—C17—C16	120.0 (4)	C39B—C40B—C35B	120.0
C12—C17—H17	120.0	C39B—C40B—H40B	120.0
C16—C17—H17	120.0	C35B—C40B—H40B	120.0
N4—Co—N1—C1	159.7 (2)	C6—C7—C8—C34A	54.4 (7)
N2—Co—N1—C1	−16.4 (2)	C8—N4—C9—C10	176.6 (2)
Cl1—Co—N1—C1	−108.4 (2)	Co—N4—C9—C10	−44.8 (2)
Cl2—Co—N1—C1	72.1 (2)	C1—N1—C10—C9	177.0 (2)
N4—Co—N1—C10	−12.12 (17)	Co—N1—C10—C9	−10.5 (3)
N2—Co—N1—C10	171.72 (17)	N4—C9—C10—N1	35.8 (3)
Cl1—Co—N1—C10	79.72 (17)	N1—C1—C11—C12	−146.9 (3)
Cl2—Co—N1—C10	−99.78 (17)	C2—C1—C11—C12	36.6 (4)
N1—Co—N2—C4	−147.55 (17)	C1—C11—C12—C13	−100.9 (4)
N3—Co—N2—C4	33.62 (16)	C1—C11—C12—C17	76.4 (4)
Cl1—Co—N2—C4	−57.49 (16)	C17—C12—C13—C14	−0.8 (5)
Cl2—Co—N2—C4	122.50 (16)	C11—C12—C13—C14	176.6 (3)
N1—Co—N2—C3	−11.10 (19)	C12—C13—C14—C15	0.0 (5)
N3—Co—N2—C3	170.07 (19)	C13—C14—C15—C16	0.3 (6)
Cl1—Co—N2—C3	78.97 (18)	C14—C15—C16—C17	0.1 (7)
Cl2—Co—N2—C3	−101.05 (18)	C13—C12—C17—C16	1.2 (5)
N4—Co—N3—C6	−20.2 (2)	C11—C12—C17—C16	−176.2 (4)
N2—Co—N3—C6	156.0 (2)	C15—C16—C17—C12	−0.9 (7)
Cl1—Co—N3—C6	−112.1 (2)	N2—C3—C19—C20	−173.9 (2)
Cl2—Co—N3—C6	67.4 (2)	C18—C3—C19—C20	63.4 (3)
N4—Co—N3—C5	172.08 (17)	C2—C3—C19—C20	−59.5 (3)
N2—Co—N3—C5	−11.75 (17)	C3—C19—C20—C21	99.1 (3)
Cl1—Co—N3—C5	80.12 (16)	C3—C19—C20—C25	−83.0 (3)
Cl2—Co—N3—C5	−100.38 (16)	C25—C20—C21—C22	0.7 (4)
N1—Co—N4—C9	32.08 (16)	C19—C20—C21—C22	178.6 (3)
N3—Co—N4—C9	−149.10 (16)	C20—C21—C22—C23	−0.2 (5)
Cl1—Co—N4—C9	−57.59 (16)	C21—C22—C23—C24	0.0 (5)
Cl2—Co—N4—C9	122.43 (16)	C22—C23—C24—C25	−0.5 (5)
N1—Co—N4—C8	168.8 (2)	C23—C24—C25—C20	1.0 (5)
N3—Co—N4—C8	−12.35 (19)	C21—C20—C25—C24	−1.1 (4)
Cl1—Co—N4—C8	79.16 (18)	C19—C20—C25—C24	−179.0 (3)
Cl2—Co—N4—C8	−100.83 (18)	N3—C6—C26—C27	114.5 (3)
C10—N1—C1—C2	172.4 (2)	C7—C6—C26—C27	−60.0 (3)
Co—N1—C1—C2	1.0 (4)	C6—C26—C27—C28	117.1 (3)
C10—N1—C1—C11	−4.0 (4)	C6—C26—C27—C32	−62.3 (3)
Co—N1—C1—C11	−175.4 (2)	C32—C27—C28—C29	−0.6 (4)
N1—C1—C2—C3	47.3 (4)	C26—C27—C28—C29	179.9 (3)
C11—C1—C2—C3	−136.2 (3)	C27—C28—C29—C30	0.4 (5)
C4—N2—C3—C18	59.2 (3)	C28—C29—C30—C31	0.2 (5)
Co—N2—C3—C18	−73.0 (2)	C29—C30—C31—C32	−0.6 (4)
C4—N2—C3—C2	−179.6 (2)	C30—C31—C32—C27	0.4 (4)
Co—N2—C3—C2	48.2 (2)	C28—C27—C32—C31	0.2 (4)
C4—N2—C3—C19	−62.3 (3)	C26—C27—C32—C31	179.7 (2)
Co—N2—C3—C19	165.48 (17)	N4—C8—C34A—C35A	−175.9 (8)
C1—C2—C3—N2	−70.3 (3)	C33—C8—C34A—C35A	−54.6 (11)
C1—C2—C3—C18	51.6 (3)	C7—C8—C34A—C35A	66.0 (11)
C1—C2—C3—C19	174.0 (2)	C8—C34A—C35A—C36A	95.3 (10)
C3—N2—C4—C5	174.1 (2)	C8—C34A—C35A—C40A	−87.4 (9)
Co—N2—C4—C5	−48.0 (2)	C40A—C35A—C36A—C37A	0.0
C6—N3—C5—C4	178.9 (2)	C34A—C35A—C36A—C37A	177.3 (6)
Co—N3—C5—C4	−12.5 (3)	C35A—C36A—C37A—C38A	0.0
N2—C4—C5—N3	39.2 (3)	C36A—C37A—C38A—C39A	0.0
C5—N3—C6—C7	177.1 (2)	C37A—C38A—C39A—C40A	0.0
Co—N3—C6—C7	10.1 (4)	C38A—C39A—C40A—C35A	0.0
C5—N3—C6—C26	3.0 (4)	C36A—C35A—C40A—C39A	0.0
Co—N3—C6—C26	−163.99 (19)	C34A—C35A—C40A—C39A	−177.2 (6)
N3—C6—C7—C8	37.7 (4)	N4—C8—C34B—C35B	165 (2)
C26—C6—C7—C8	−147.7 (2)	C33—C8—C34B—C35B	−76 (3)
C9—N4—C8—C33	−62.9 (3)	C7—C8—C34B—C35B	43 (3)
Co—N4—C8—C33	164.00 (18)	C8—C34B—C35B—C36B	79 (3)
C9—N4—C8—C7	−178.2 (2)	C8—C34B—C35B—C40B	−95 (3)
Co—N4—C8—C7	48.7 (3)	C40B—C35B—C36B—C37B	0.0
C9—N4—C8—C34B	55.5 (17)	C34B—C35B—C36B—C37B	−173.2 (16)
Co—N4—C8—C34B	−77.6 (17)	C35B—C36B—C37B—C38B	0.0
C9—N4—C8—C34A	60.3 (7)	C36B—C37B—C38B—C39B	0.0
Co—N4—C8—C34A	−72.8 (6)	C37B—C38B—C39B—C40B	0.0
C6—C7—C8—N4	−66.1 (3)	C38B—C39B—C40B—C35B	0.0
C6—C7—C8—C33	177.7 (2)	C36B—C35B—C40B—C39B	0.0
C6—C7—C8—C34B	57.6 (19)	C34B—C35B—C40B—C39B	173.3 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O1	0.88 (3)	2.24 (3)	3.063 (4)	155 (2)
N4—H4n···Cl2i	0.88 (3)	2.64 (2)	3.432 (2)	150 (3)
C10—H10a···O3ii	0.99	2.50	3.437 (4)	159
C19—H19b···O1iii	0.99	2.54	3.409 (4)	147
C38a—H38a···O4iv	0.95	2.57	3.480 (3)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O1	0.88 (3)	2.24 (3)	3.063 (4)	155 (2)
N4—H4n⋯Cl2i	0.88 (3)	2.64 (2)	3.432 (2)	150 (3)
C10—H10a⋯O3ii	0.99	2.50	3.437 (4)	159
C19—H19b⋯O1iii	0.99	2.54	3.409 (4)	147
C38a—H38a⋯O4iv	0.95	2.57	3.480 (3)	160

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