(N-n-Butyl-pyridine-4-carbothio-amide-κN)chloridobis(dimethyl-glyoximato-κN,N')cobalt(III) hemihydrate.

The title compound, trans-[Co(C(4)H(7)N(2)O(2))(2)Cl(C(10)H(14)N(2)S)]·0.5H(2)O, contains two independent mol-ecules in the asymmetric unit in which the Co(III) ions are coordinated in slightly distorted octa-hedral coordination environments. The bis-chelating glyoximate ligands, which occupy equatorial sites, are linked by interligand O-H⋯O hydrogen bonds. The dihedral angles between the mean planes of the glyoximate ligands in each mol-ecule are 2.07 (8) and 1.60 (1)°. The asymmetric unit contains a solvent water mol-ecule which is disordered over two sites with refined occupancies 0.64 (2) and 0.36 (2).

Related literature

For a related structure, see: Kavitha et al. (2008 ▶). For background, see: Trogler et al. (1974 ▶); Dolphin (1982 ▶); Bresciani-Pahor et al. (1985 ▶); Geno & Halpern (1987 ▶); Englert et al. (1999 ▶, 2000 ▶). For the synthetic prodedure, see: Schrauzer & Kohnel (1964 ▶); Ramesh et al. (2008 ▶).

Experimental

Crystal data

[Co(C4H7N2O2)2Cl(C10H14N2S)]·0.5H2O

M = 526.90

Monoclinic,

a = 11.1976 (5) Å

b = 14.7889 (7) Å

c = 28.8482 (14) Å

β = 95.748 (2)°

V = 4753.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.96 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.742, T max = 0.853

50767 measured reflections

10297 independent reflections

7510 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.168

S = 1.06

10297 reflections

606 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.96 e Å−3

Δρmin = −0.82 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022661/lh2818sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022661/lh2818Isup2.hkl

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

Enhanced figure: interactive version of Fig. 1

[Co(C4H7N2O2)2Cl(C10H14N2S)]·0.5H2O	F(000) = 2192
Mr = 526.90	Dx = 1.473 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5420 reflections
a = 11.1976 (5) Å	θ = 2.5–26.0°
b = 14.7889 (7) Å	µ = 0.96 mm−1
c = 28.8482 (14) Å	T = 293 K
β = 95.748 (2)°	Needle, brown
V = 4753.2 (4) Å3	0.3 × 0.2 × 0.2 mm
Z = 8

Bruker Kappa-APEX2 diffractometer	10297 independent reflections
Radiation source: fine-focus sealed tube	7510 reflections with I > 2σ(I)
graphite	Rint = 0.044
Detector resolution: 0 pixels mm-1	θmax = 26.9°, θmin = 1.4°
ω and φ scans	h = −14→10
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −18→18
Tmin = 0.742, Tmax = 0.853	l = −36→36
50767 measured reflections

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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.168	w = 1/[σ2(Fo2) + (0.0927P)2 + 3.9112P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.009
10297 reflections	Δρmax = 0.96 e Å−3
606 parameters	Δρmin = −0.82 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (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 > 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	Occ. (<1)
C1	0.6540 (3)	0.4012 (2)	0.14607 (12)	0.0391 (8)
C2	0.5817 (3)	0.3183 (3)	0.13929 (13)	0.0395 (8)
C3	0.7787 (4)	0.2495 (3)	−0.01437 (14)	0.0480 (9)
C4	0.8518 (3)	0.3305 (3)	−0.00758 (13)	0.0432 (9)
C5	0.6493 (4)	0.4620 (3)	0.18669 (13)	0.0548 (11)
H5A	0.6895	0.5177	0.1811	0.082*
H5B	0.6884	0.4335	0.2140	0.082*
H5C	0.5671	0.4742	0.1913	0.082*
C6	0.4897 (4)	0.2917 (3)	0.17091 (16)	0.0579 (12)
H6A	0.4253	0.3348	0.1682	0.087*
H6B	0.5259	0.2903	0.2025	0.087*
H6C	0.4587	0.2329	0.1623	0.087*
C7	0.7738 (6)	0.1895 (4)	−0.05624 (19)	0.091 (2)
H7A	0.7375	0.1328	−0.0494	0.137*
H7B	0.8537	0.1790	−0.0644	0.137*
H7C	0.7270	0.2180	−0.0818	0.137*
C8	0.9383 (4)	0.3614 (3)	−0.04059 (15)	0.0570 (11)
H8A	0.9657	0.4213	−0.0323	0.085*
H8B	0.8991	0.3618	−0.0717	0.085*
H8C	1.0056	0.3209	−0.0389	0.085*
C9	0.8419 (4)	0.1681 (3)	0.10754 (17)	0.0542 (11)
H9	0.7787	0.1375	0.0911	0.065*
C10	0.9260 (4)	0.1193 (3)	0.13510 (17)	0.0587 (12)
H10	0.9197	0.0567	0.1368	0.070*
C11	1.0198 (4)	0.1636 (3)	0.16024 (14)	0.0486 (10)
C12	1.0274 (4)	0.2554 (3)	0.15450 (16)	0.0536 (10)
H12	1.0911	0.2873	0.1698	0.064*
C13	0.9412 (4)	0.3003 (3)	0.12621 (14)	0.0458 (9)
H13	0.9481	0.3626	0.1227	0.055*
C14	1.1118 (4)	0.1146 (4)	0.19326 (17)	0.0641 (12)
C15	1.1459 (6)	−0.0284 (5)	0.2383 (2)	0.0906 (19)
H15A	1.1778	0.0094	0.2641	0.109*
H15B	1.0891	−0.0699	0.2501	0.109*
C16	1.2409 (7)	−0.0793 (5)	0.2233 (2)	0.113 (3)
H16A	1.2700	−0.1194	0.2485	0.136*
H16B	1.3056	−0.0376	0.2186	0.136*
C17	1.2186 (6)	−0.1359 (5)	0.1797 (2)	0.0895 (18)
H17A	1.1807	−0.0978	0.1551	0.107*
H17B	1.2957	−0.1545	0.1704	0.107*
C18	1.1436 (6)	−0.2176 (5)	0.1829 (3)	0.107 (2)
H18A	1.1685	−0.2491	0.2114	0.161*
H18B	1.1528	−0.2564	0.1569	0.161*
H18C	1.0610	−0.2002	0.1827	0.161*
C19	0.8873 (4)	0.4019 (3)	0.40245 (15)	0.0548 (11)
C20	0.9481 (4)	0.4264 (3)	0.36220 (16)	0.0510 (10)
C21	0.7077 (4)	0.1755 (3)	0.26363 (13)	0.0442 (9)
C22	0.6402 (3)	0.1546 (3)	0.30342 (14)	0.0441 (9)
C23	0.9121 (6)	0.4454 (4)	0.44954 (18)	0.0843 (18)
H23A	0.8644	0.4167	0.4712	0.126*
H23B	0.8920	0.5085	0.4473	0.126*
H23C	0.9956	0.4389	0.4602	0.126*
C24	1.0394 (5)	0.4994 (3)	0.3627 (2)	0.0781 (16)
H24A	1.0620	0.5080	0.3317	0.117*
H24B	1.1088	0.4828	0.3831	0.117*
H24C	1.0063	0.5545	0.3734	0.117*
C25	0.6947 (5)	0.1242 (3)	0.21891 (16)	0.0650 (13)
H25A	0.7317	0.1575	0.1956	0.098*
H25B	0.6111	0.1157	0.2089	0.098*
H25C	0.7330	0.0663	0.2234	0.098*
C26	0.5420 (4)	0.0867 (3)	0.3009 (2)	0.0681 (13)
H26A	0.5214	0.0740	0.3317	0.102*
H26B	0.5682	0.0321	0.2871	0.102*
H26C	0.4731	0.1102	0.2823	0.102*
C27	0.9110 (3)	0.1502 (2)	0.38996 (12)	0.0374 (8)
H27	0.8439	0.1560	0.4063	0.045*
C28	0.9965 (3)	0.0876 (3)	0.40509 (12)	0.0375 (8)
H28	0.9862	0.0517	0.4309	0.045*
C29	1.0991 (3)	0.0776 (2)	0.38179 (12)	0.0361 (8)
C30	1.1068 (4)	0.1332 (3)	0.34363 (14)	0.0447 (9)
H30	1.1735	0.1293	0.3270	0.054*
C31	1.0177 (4)	0.1937 (3)	0.33005 (14)	0.0430 (9)
H31	1.0254	0.2296	0.3040	0.052*
C32	1.1937 (3)	0.0082 (3)	0.39541 (13)	0.0397 (8)
C33	1.2757 (4)	−0.0957 (3)	0.45690 (15)	0.0512 (10)
H33A	1.2829	−0.0937	0.4907	0.061*
H33B	1.3549	−0.0859	0.4469	0.061*
C34	1.2308 (4)	−0.1880 (3)	0.44078 (18)	0.0555 (11)
H34A	1.1529	−0.1982	0.4518	0.067*
H34B	1.2202	−0.1887	0.4070	0.067*
C35	1.3131 (4)	−0.2642 (3)	0.45739 (17)	0.0588 (11)
H35A	1.3197	−0.2665	0.4912	0.071*
H35B	1.3925	−0.2527	0.4480	0.071*
C36	1.2683 (5)	−0.3549 (4)	0.4380 (2)	0.0869 (18)
H36A	1.1937	−0.3695	0.4499	0.130*
H36B	1.3265	−0.4008	0.4471	0.130*
H36C	1.2564	−0.3516	0.4046	0.130*
N1	0.7222 (3)	0.4142 (2)	0.11309 (10)	0.0356 (6)
N2	0.6040 (3)	0.2735 (2)	0.10299 (10)	0.0359 (6)
N3	0.7116 (3)	0.2353 (2)	0.01918 (11)	0.0403 (7)
N4	0.8335 (3)	0.3740 (2)	0.02985 (10)	0.0355 (6)
N5	0.8476 (3)	0.2575 (2)	0.10354 (10)	0.0347 (6)
N6	1.0805 (4)	0.0297 (3)	0.20319 (16)	0.0767 (13)
N7	0.8069 (3)	0.3394 (2)	0.39383 (11)	0.0465 (8)
N8	0.9133 (3)	0.3797 (2)	0.32561 (12)	0.0444 (8)
N9	0.7812 (3)	0.2424 (2)	0.27193 (10)	0.0388 (7)
N10	0.6723 (3)	0.2043 (2)	0.33924 (11)	0.0409 (7)
N11	0.9195 (3)	0.20336 (19)	0.35282 (10)	0.0331 (6)
N12	1.1953 (3)	−0.0228 (2)	0.43840 (12)	0.0465 (8)
O1	0.7913 (3)	0.48767 (17)	0.11270 (9)	0.0465 (6)
O2	0.5463 (3)	0.19640 (18)	0.09123 (11)	0.0504 (7)
O3	0.6361 (3)	0.1655 (2)	0.01808 (11)	0.0589 (8)
O4	0.8906 (2)	0.45087 (19)	0.04153 (10)	0.0470 (6)
O5	0.7379 (3)	0.3099 (2)	0.42581 (10)	0.0642 (9)
O6	0.9561 (3)	0.3945 (2)	0.28445 (11)	0.0569 (8)
O7	0.8475 (3)	0.2714 (2)	0.23890 (10)	0.0545 (7)
O8	0.6170 (3)	0.1955 (2)	0.37864 (11)	0.0570 (8)
O9	0.5206 (13)	0.4306 (11)	0.4152 (10)	0.117 (9)	0.36 (2)
O9'	0.563 (2)	0.4610 (14)	0.4517 (9)	0.258 (10)	0.64 (2)
S1	1.22943 (19)	0.16153 (15)	0.21468 (9)	0.1222 (8)
S2	1.28739 (11)	−0.02367 (9)	0.35816 (4)	0.0642 (3)
Cl1	0.57535 (8)	0.39973 (6)	0.02391 (3)	0.0401 (2)
Cl2	0.65579 (9)	0.39511 (7)	0.31055 (4)	0.0494 (3)
Co1	0.71972 (4)	0.32373 (3)	0.066535 (15)	0.02991 (14)
Co2	0.79476 (4)	0.29152 (3)	0.333079 (16)	0.03392 (14)
H1	0.829 (5)	0.480 (4)	0.076 (2)	0.092 (17)*
H2	0.566 (5)	0.181 (4)	0.055 (2)	0.090 (18)*
H8	0.670 (6)	0.244 (5)	0.406 (3)	0.13 (2)*
H7	0.890 (6)	0.323 (5)	0.254 (3)	0.13 (3)*

	U11	U22	U33	U12	U13	U23
C1	0.051 (2)	0.039 (2)	0.0281 (17)	0.0090 (16)	0.0051 (15)	0.0082 (15)
C2	0.0390 (19)	0.046 (2)	0.0340 (19)	0.0050 (16)	0.0060 (15)	0.0135 (16)
C3	0.060 (2)	0.046 (2)	0.039 (2)	0.0048 (19)	0.0079 (18)	−0.0063 (17)
C4	0.044 (2)	0.047 (2)	0.040 (2)	0.0068 (17)	0.0091 (16)	0.0049 (17)
C5	0.077 (3)	0.055 (3)	0.032 (2)	0.011 (2)	0.006 (2)	0.0002 (18)
C6	0.055 (2)	0.071 (3)	0.051 (3)	0.008 (2)	0.020 (2)	0.021 (2)
C7	0.138 (6)	0.084 (4)	0.056 (3)	−0.013 (4)	0.031 (3)	−0.029 (3)
C8	0.055 (2)	0.076 (3)	0.043 (2)	0.004 (2)	0.0205 (19)	0.004 (2)
C9	0.054 (2)	0.039 (2)	0.067 (3)	−0.0056 (19)	−0.009 (2)	0.010 (2)
C10	0.059 (3)	0.039 (2)	0.075 (3)	−0.0016 (19)	−0.008 (2)	0.018 (2)
C11	0.046 (2)	0.056 (3)	0.043 (2)	0.0080 (19)	0.0039 (17)	0.0119 (19)
C12	0.048 (2)	0.053 (3)	0.057 (3)	−0.0051 (19)	−0.0082 (19)	0.005 (2)
C13	0.046 (2)	0.039 (2)	0.051 (2)	−0.0044 (17)	−0.0002 (18)	0.0059 (18)
C14	0.062 (3)	0.073 (3)	0.056 (3)	0.011 (2)	−0.002 (2)	0.009 (2)
C15	0.114 (5)	0.095 (5)	0.060 (3)	0.035 (4)	−0.003 (3)	0.008 (3)
C16	0.132 (6)	0.127 (6)	0.073 (4)	0.057 (5)	−0.023 (4)	−0.020 (4)
C17	0.090 (4)	0.094 (5)	0.083 (4)	0.018 (4)	0.000 (3)	−0.022 (4)
C18	0.077 (4)	0.123 (6)	0.123 (6)	−0.002 (4)	0.016 (4)	−0.013 (5)
C19	0.070 (3)	0.041 (2)	0.049 (2)	0.020 (2)	−0.015 (2)	−0.0140 (19)
C20	0.050 (2)	0.0300 (19)	0.070 (3)	0.0063 (17)	−0.010 (2)	−0.0070 (19)
C21	0.053 (2)	0.039 (2)	0.039 (2)	0.0093 (18)	−0.0025 (17)	−0.0019 (16)
C22	0.042 (2)	0.037 (2)	0.052 (2)	0.0029 (16)	0.0001 (17)	0.0060 (18)
C23	0.116 (5)	0.067 (3)	0.062 (3)	0.021 (3)	−0.029 (3)	−0.028 (3)
C24	0.069 (3)	0.042 (3)	0.120 (5)	−0.004 (2)	−0.008 (3)	−0.015 (3)
C25	0.091 (4)	0.054 (3)	0.047 (3)	0.004 (2)	−0.006 (2)	−0.014 (2)
C26	0.058 (3)	0.059 (3)	0.086 (4)	−0.012 (2)	−0.002 (2)	0.008 (3)
C27	0.0402 (18)	0.042 (2)	0.0309 (18)	0.0037 (16)	0.0081 (14)	0.0000 (15)
C28	0.0417 (19)	0.042 (2)	0.0288 (17)	0.0010 (16)	0.0030 (14)	0.0023 (15)
C29	0.0375 (18)	0.0343 (18)	0.0368 (18)	0.0001 (15)	0.0051 (14)	−0.0064 (15)
C30	0.045 (2)	0.040 (2)	0.052 (2)	0.0029 (17)	0.0173 (17)	0.0030 (18)
C31	0.050 (2)	0.0361 (19)	0.045 (2)	0.0023 (16)	0.0187 (17)	0.0075 (16)
C32	0.0373 (18)	0.0371 (19)	0.044 (2)	−0.0007 (15)	−0.0009 (15)	−0.0043 (16)
C33	0.048 (2)	0.054 (2)	0.049 (2)	0.0111 (19)	−0.0052 (18)	0.004 (2)
C34	0.046 (2)	0.051 (2)	0.069 (3)	0.0056 (19)	−0.002 (2)	0.007 (2)
C35	0.058 (3)	0.056 (3)	0.062 (3)	0.007 (2)	0.000 (2)	0.009 (2)
C36	0.088 (4)	0.051 (3)	0.119 (5)	0.007 (3)	0.000 (4)	0.001 (3)
N1	0.0434 (16)	0.0311 (15)	0.0319 (15)	−0.0013 (12)	0.0025 (12)	0.0033 (12)
N2	0.0349 (15)	0.0338 (15)	0.0393 (16)	−0.0028 (12)	0.0060 (12)	0.0079 (13)
N3	0.0486 (17)	0.0327 (16)	0.0391 (17)	−0.0030 (13)	0.0017 (14)	−0.0028 (13)
N4	0.0390 (15)	0.0349 (16)	0.0333 (15)	−0.0028 (13)	0.0069 (12)	0.0044 (12)
N5	0.0363 (15)	0.0330 (15)	0.0353 (15)	−0.0023 (12)	0.0066 (12)	0.0036 (12)
N6	0.092 (3)	0.061 (3)	0.074 (3)	0.022 (2)	−0.009 (2)	0.017 (2)
N7	0.062 (2)	0.0415 (19)	0.0356 (17)	0.0155 (16)	0.0042 (15)	−0.0054 (14)
N8	0.0500 (18)	0.0311 (16)	0.0513 (19)	0.0065 (14)	0.0022 (15)	0.0021 (14)
N9	0.0497 (17)	0.0362 (16)	0.0315 (15)	0.0042 (14)	0.0088 (13)	0.0021 (13)
N10	0.0433 (17)	0.0425 (17)	0.0382 (17)	0.0051 (14)	0.0099 (13)	0.0057 (14)
N11	0.0403 (15)	0.0281 (14)	0.0313 (15)	0.0018 (12)	0.0053 (12)	−0.0008 (12)
N12	0.0441 (17)	0.0459 (19)	0.0483 (19)	0.0084 (15)	−0.0002 (14)	0.0053 (15)
O1	0.0613 (17)	0.0344 (14)	0.0440 (15)	−0.0121 (12)	0.0056 (13)	−0.0032 (12)
O2	0.0487 (16)	0.0403 (15)	0.0625 (19)	−0.0163 (12)	0.0079 (14)	0.0053 (13)
O3	0.073 (2)	0.0419 (16)	0.0602 (19)	−0.0208 (15)	0.0010 (16)	−0.0103 (14)
O4	0.0496 (15)	0.0447 (15)	0.0475 (15)	−0.0196 (13)	0.0094 (12)	0.0037 (12)
O5	0.089 (2)	0.070 (2)	0.0364 (16)	0.0175 (18)	0.0160 (16)	−0.0037 (15)
O6	0.0630 (18)	0.0475 (17)	0.0631 (19)	−0.0028 (14)	0.0211 (15)	0.0125 (14)
O7	0.074 (2)	0.0575 (19)	0.0352 (15)	0.0007 (16)	0.0202 (14)	0.0040 (13)
O8	0.0560 (17)	0.068 (2)	0.0516 (18)	0.0074 (15)	0.0273 (14)	0.0159 (15)
O9	0.071 (9)	0.089 (10)	0.20 (2)	0.009 (7)	0.048 (10)	−0.003 (11)
O9'	0.34 (2)	0.181 (15)	0.24 (2)	0.073 (15)	−0.035 (18)	0.031 (15)
S1	0.1044 (13)	0.1075 (15)	0.1419 (18)	−0.0176 (11)	−0.0507 (13)	0.0240 (13)
S2	0.0658 (7)	0.0746 (8)	0.0535 (7)	0.0232 (6)	0.0127 (6)	0.0032 (6)
Cl1	0.0417 (5)	0.0443 (5)	0.0342 (4)	0.0051 (4)	0.0029 (3)	0.0077 (4)
Cl2	0.0552 (6)	0.0440 (5)	0.0482 (5)	0.0141 (4)	0.0019 (4)	0.0042 (4)
Co1	0.0343 (2)	0.0272 (2)	0.0284 (2)	−0.00359 (18)	0.00409 (18)	0.00201 (18)
Co2	0.0419 (3)	0.0305 (3)	0.0297 (3)	0.0035 (2)	0.00545 (19)	0.00001 (19)

C1—N1	1.293 (4)	C24—H24B	0.9600
C1—C2	1.471 (5)	C24—H24C	0.9600
C1—C5	1.483 (5)	C25—H25A	0.9600
C2—N2	1.284 (5)	C25—H25B	0.9600
C2—C6	1.496 (5)	C25—H25C	0.9600
C3—N3	1.300 (5)	C26—H26A	0.9600
C3—C4	1.453 (6)	C26—H26B	0.9600
C3—C7	1.495 (6)	C26—H26C	0.9600
C4—N4	1.291 (5)	C27—N11	1.340 (4)
C4—C8	1.496 (5)	C27—C28	1.371 (5)
C5—H5A	0.9600	C27—H27	0.9300
C5—H5B	0.9600	C28—C29	1.395 (5)
C5—H5C	0.9600	C28—H28	0.9300
C6—H6A	0.9600	C29—C30	1.383 (5)
C6—H6B	0.9600	C29—C32	1.499 (5)
C6—H6C	0.9600	C30—C31	1.368 (5)
C7—H7A	0.9600	C30—H30	0.9300
C7—H7B	0.9600	C31—N11	1.343 (5)
C7—H7C	0.9600	C31—H31	0.9300
C8—H8A	0.9600	C32—N12	1.321 (5)
C8—H8B	0.9600	C32—S2	1.644 (4)
C8—H8C	0.9600	C33—N12	1.469 (5)
C9—N5	1.330 (5)	C33—C34	1.512 (6)
C9—C10	1.374 (6)	C33—H33A	0.9700
C9—H9	0.9300	C33—H33B	0.9700
C10—C11	1.381 (6)	C34—C35	1.503 (6)
C10—H10	0.9300	C34—H34A	0.9700
C11—C12	1.371 (6)	C34—H34B	0.9700
C11—C14	1.516 (6)	C35—C36	1.519 (7)
C12—C13	1.371 (6)	C35—H35A	0.9700
C12—H12	0.9300	C35—H35B	0.9700
C13—N5	1.337 (5)	C36—H36A	0.9600
C13—H13	0.9300	C36—H36B	0.9600
C14—N6	1.343 (7)	C36—H36C	0.9600
C14—S1	1.560 (5)	N1—O1	1.335 (4)
C15—C16	1.407 (8)	N1—Co1	1.894 (3)
C15—N6	1.467 (6)	N2—O2	1.338 (4)
C15—H15A	0.9700	N2—Co1	1.900 (3)
C15—H15B	0.9700	N3—O3	1.333 (4)
C16—C17	1.510 (8)	N3—Co1	1.887 (3)
C16—H16A	0.9700	N4—O4	1.331 (4)
C16—H16B	0.9700	N4—Co1	1.889 (3)
C17—C18	1.480 (9)	N5—Co1	1.960 (3)
C17—H17A	0.9700	N7—O5	1.334 (5)
C17—H17B	0.9700	N7—Co2	1.882 (3)
C18—H18A	0.9600	N8—O6	1.343 (4)
C18—H18B	0.9600	N8—Co2	1.888 (3)
C18—H18C	0.9600	N9—O7	1.336 (4)
C19—N7	1.297 (6)	N9—Co2	1.900 (3)
C19—C20	1.450 (7)	N10—O8	1.354 (4)
C19—C23	1.504 (6)	N10—Co2	1.904 (3)
C20—N8	1.288 (5)	N11—Co2	1.954 (3)
C20—C24	1.486 (6)	O1—H1	1.20 (6)
C21—N9	1.293 (5)	O2—H2	1.12 (6)
C21—C22	1.469 (6)	O3—H2	1.39 (6)
C21—C25	1.492 (6)	O4—H1	1.32 (6)
C22—N10	1.290 (5)	O5—H8	1.34 (8)
C22—C26	1.485 (6)	O7—H7	0.98 (7)
C23—H23A	0.9600	O8—H8	1.17 (8)
C23—H23B	0.9600	Cl1—Co1	2.2341 (10)
C23—H23C	0.9600	Cl2—Co2	2.2334 (10)
C24—H24A	0.9600
N1—C1—C2	112.6 (3)	H26B—C26—H26C	109.5
N1—C1—C5	124.2 (4)	N11—C27—C28	123.2 (3)
C2—C1—C5	123.3 (3)	N11—C27—H27	118.4
N2—C2—C1	112.9 (3)	C28—C27—H27	118.4
N2—C2—C6	124.3 (4)	C27—C28—C29	120.0 (3)
C1—C2—C6	122.8 (4)	C27—C28—H28	120.0
N3—C3—C4	113.1 (3)	C29—C28—H28	120.0
N3—C3—C7	121.9 (4)	C30—C29—C28	116.2 (3)
C4—C3—C7	125.0 (4)	C30—C29—C32	121.1 (3)
N4—C4—C3	112.9 (3)	C28—C29—C32	122.7 (3)
N4—C4—C8	123.2 (4)	C31—C30—C29	121.0 (3)
C3—C4—C8	123.9 (4)	C31—C30—H30	119.5
C1—C5—H5A	109.5	C29—C30—H30	119.5
C1—C5—H5B	109.5	N11—C31—C30	122.6 (3)
H5A—C5—H5B	109.5	N11—C31—H31	118.7
C1—C5—H5C	109.5	C30—C31—H31	118.7
H5A—C5—H5C	109.5	N12—C32—C29	115.3 (3)
H5B—C5—H5C	109.5	N12—C32—S2	124.3 (3)
C2—C6—H6A	109.5	C29—C32—S2	120.4 (3)
C2—C6—H6B	109.5	N12—C33—C34	112.2 (3)
H6A—C6—H6B	109.5	N12—C33—H33A	109.2
C2—C6—H6C	109.5	C34—C33—H33A	109.2
H6A—C6—H6C	109.5	N12—C33—H33B	109.2
H6B—C6—H6C	109.5	C34—C33—H33B	109.2
C3—C7—H7A	109.5	H33A—C33—H33B	107.9
C3—C7—H7B	109.5	C35—C34—C33	113.9 (4)
H7A—C7—H7B	109.5	C35—C34—H34A	108.8
C3—C7—H7C	109.5	C33—C34—H34A	108.8
H7A—C7—H7C	109.5	C35—C34—H34B	108.8
H7B—C7—H7C	109.5	C33—C34—H34B	108.8
C4—C8—H8A	109.5	H34A—C34—H34B	107.7
C4—C8—H8B	109.5	C34—C35—C36	112.0 (4)
H8A—C8—H8B	109.5	C34—C35—H35A	109.2
C4—C8—H8C	109.5	C36—C35—H35A	109.2
H8A—C8—H8C	109.5	C34—C35—H35B	109.2
H8B—C8—H8C	109.5	C36—C35—H35B	109.2
N5—C9—C10	122.4 (4)	H35A—C35—H35B	107.9
N5—C9—H9	118.8	C35—C36—H36A	109.5
C10—C9—H9	118.8	C35—C36—H36B	109.5
C9—C10—C11	119.7 (4)	H36A—C36—H36B	109.5
C9—C10—H10	120.1	C35—C36—H36C	109.5
C11—C10—H10	120.1	H36A—C36—H36C	109.5
C12—C11—C10	117.4 (4)	H36B—C36—H36C	109.5
C12—C11—C14	120.2 (4)	C1—N1—O1	120.9 (3)
C10—C11—C14	122.5 (4)	C1—N1—Co1	116.7 (3)
C13—C12—C11	120.2 (4)	O1—N1—Co1	122.5 (2)
C13—C12—H12	119.9	C2—N2—O2	121.2 (3)
C11—C12—H12	119.9	C2—N2—Co1	116.7 (3)
N5—C13—C12	122.1 (4)	O2—N2—Co1	122.1 (2)
N5—C13—H13	118.9	C3—N3—O3	121.3 (3)
C12—C13—H13	118.9	C3—N3—Co1	115.9 (3)
N6—C14—C11	113.9 (4)	O3—N3—Co1	122.6 (2)
N6—C14—S1	124.0 (4)	C4—N4—O4	121.7 (3)
C11—C14—S1	122.0 (4)	C4—N4—Co1	116.4 (3)
C16—C15—N6	116.1 (5)	O4—N4—Co1	121.9 (2)
C16—C15—H15A	108.3	C9—N5—C13	118.1 (3)
N6—C15—H15A	108.3	C9—N5—Co1	120.3 (3)
C16—C15—H15B	108.3	C13—N5—Co1	121.6 (3)
N6—C15—H15B	108.3	C14—N6—C15	124.9 (5)
H15A—C15—H15B	107.4	C19—N7—O5	122.6 (4)
C15—C16—C17	119.1 (6)	C19—N7—Co2	115.5 (3)
C15—C16—H16A	107.5	O5—N7—Co2	121.9 (3)
C17—C16—H16A	107.5	C20—N8—O6	122.1 (4)
C15—C16—H16B	107.5	C20—N8—Co2	115.8 (3)
C17—C16—H16B	107.5	O6—N8—Co2	122.1 (3)
H16A—C16—H16B	107.0	C21—N9—O7	120.2 (3)
C18—C17—C16	116.6 (7)	C21—N9—Co2	117.0 (3)
C18—C17—H17A	108.1	O7—N9—Co2	122.8 (3)
C16—C17—H17A	108.1	C22—N10—O8	120.2 (3)
C18—C17—H17B	108.1	C22—N10—Co2	117.2 (3)
C16—C17—H17B	108.1	O8—N10—Co2	122.6 (3)
H17A—C17—H17B	107.3	C27—N11—C31	117.1 (3)
C17—C18—H18A	109.5	C27—N11—Co2	121.2 (2)
C17—C18—H18B	109.5	C31—N11—Co2	121.7 (2)
H18A—C18—H18B	109.5	C32—N12—C33	123.1 (3)
C17—C18—H18C	109.5	N1—O1—H1	101 (3)
H18A—C18—H18C	109.5	N2—O2—H2	106 (3)
H18B—C18—H18C	109.5	N3—O3—H2	105 (2)
N7—C19—C20	113.4 (4)	N4—O4—H1	101 (2)
N7—C19—C23	122.7 (5)	N7—O5—H8	106 (3)
C20—C19—C23	123.9 (5)	N9—O7—H7	102 (4)
N8—C20—C19	113.3 (4)	N10—O8—H8	105 (3)
N8—C20—C24	123.2 (5)	N3—Co1—N4	81.56 (13)
C19—C20—C24	123.5 (4)	N3—Co1—N1	177.86 (13)
N9—C21—C22	112.6 (3)	N4—Co1—N1	99.01 (13)
N9—C21—C25	123.7 (4)	N3—Co1—N2	98.28 (13)
C22—C21—C25	123.7 (4)	N4—Co1—N2	179.43 (13)
N10—C22—C21	112.4 (3)	N1—Co1—N2	81.13 (13)
N10—C22—C26	124.8 (4)	N3—Co1—N5	91.58 (13)
C21—C22—C26	122.7 (4)	N4—Co1—N5	90.24 (12)
C19—C23—H23A	109.5	N1—Co1—N5	90.48 (12)
C19—C23—H23B	109.5	N2—Co1—N5	90.30 (12)
H23A—C23—H23B	109.5	N3—Co1—Cl1	88.31 (10)
C19—C23—H23C	109.5	N4—Co1—Cl1	89.16 (9)
H23A—C23—H23C	109.5	N1—Co1—Cl1	89.63 (9)
H23B—C23—H23C	109.5	N2—Co1—Cl1	90.29 (9)
C20—C24—H24A	109.5	N5—Co1—Cl1	179.40 (9)
C20—C24—H24B	109.5	N7—Co2—N8	81.99 (15)
H24A—C24—H24B	109.5	N7—Co2—N9	179.39 (15)
C20—C24—H24C	109.5	N8—Co2—N9	98.62 (14)
H24A—C24—H24C	109.5	N7—Co2—N10	98.81 (15)
H24B—C24—H24C	109.5	N8—Co2—N10	178.35 (14)
C21—C25—H25A	109.5	N9—Co2—N10	80.58 (13)
C21—C25—H25B	109.5	N7—Co2—N11	89.81 (13)
H25A—C25—H25B	109.5	N8—Co2—N11	90.22 (13)
C21—C25—H25C	109.5	N9—Co2—N11	90.19 (12)
H25A—C25—H25C	109.5	N10—Co2—N11	91.23 (13)
H25B—C25—H25C	109.5	N7—Co2—Cl2	89.78 (10)
C22—C26—H26A	109.5	N8—Co2—Cl2	88.30 (10)
C22—C26—H26B	109.5	N9—Co2—Cl2	90.23 (10)
H26A—C26—H26B	109.5	N10—Co2—Cl2	90.26 (10)
C22—C26—H26C	109.5	N11—Co2—Cl2	178.50 (9)
H26A—C26—H26C	109.5
N1—C1—C2—N2	2.5 (5)	O3—N3—Co1—N5	92.6 (3)
C5—C1—C2—N2	−176.8 (3)	C3—N3—Co1—Cl1	87.6 (3)
N1—C1—C2—C6	−175.7 (3)	O3—N3—Co1—Cl1	−87.9 (3)
C5—C1—C2—C6	4.9 (6)	C4—N4—Co1—N3	0.8 (3)
N3—C3—C4—N4	−1.7 (5)	O4—N4—Co1—N3	179.7 (3)
C7—C3—C4—N4	175.3 (5)	C4—N4—Co1—N1	−177.1 (3)
N3—C3—C4—C8	178.9 (4)	O4—N4—Co1—N1	1.8 (3)
C7—C3—C4—C8	−4.1 (7)	C4—N4—Co1—N2	−73 (15)
N5—C9—C10—C11	0.8 (7)	O4—N4—Co1—N2	106 (15)
C9—C10—C11—C12	−3.1 (7)	C4—N4—Co1—N5	92.3 (3)
C9—C10—C11—C14	176.7 (4)	O4—N4—Co1—N5	−88.7 (3)
C10—C11—C12—C13	2.7 (7)	C4—N4—Co1—Cl1	−87.6 (3)
C14—C11—C12—C13	−177.2 (4)	O4—N4—Co1—Cl1	91.3 (3)
C11—C12—C13—N5	0.2 (7)	C1—N1—Co1—N3	76 (4)
C12—C11—C14—N6	166.6 (5)	O1—N1—Co1—N3	−105 (3)
C10—C11—C14—N6	−13.2 (7)	C1—N1—Co1—N4	−178.7 (3)
C12—C11—C14—S1	−11.3 (6)	O1—N1—Co1—N4	0.6 (3)
C10—C11—C14—S1	168.9 (4)	C1—N1—Co1—N2	1.8 (3)
N6—C15—C16—C17	−51.0 (11)	O1—N1—Co1—N2	−178.8 (3)
C15—C16—C17—C18	−71.2 (9)	C1—N1—Co1—N5	−88.4 (3)
N7—C19—C20—N8	−1.8 (5)	O1—N1—Co1—N5	91.0 (3)
C23—C19—C20—N8	179.4 (4)	C1—N1—Co1—Cl1	92.2 (3)
N7—C19—C20—C24	176.9 (4)	O1—N1—Co1—Cl1	−88.4 (3)
C23—C19—C20—C24	−1.9 (7)	C2—N2—Co1—N3	−178.2 (3)
N9—C21—C22—N10	−3.2 (5)	O2—N2—Co1—N3	0.5 (3)
C25—C21—C22—N10	175.7 (4)	C2—N2—Co1—N4	−105 (15)
N9—C21—C22—C26	173.9 (4)	O2—N2—Co1—N4	74 (15)
C25—C21—C22—C26	−7.2 (6)	C2—N2—Co1—N1	−0.3 (3)
N11—C27—C28—C29	0.7 (6)	O2—N2—Co1—N1	178.4 (3)
C27—C28—C29—C30	−0.4 (5)	C2—N2—Co1—N5	90.1 (3)
C27—C28—C29—C32	−177.7 (3)	O2—N2—Co1—N5	−91.2 (3)
C28—C29—C30—C31	−0.2 (6)	C2—N2—Co1—Cl1	−89.9 (3)
C32—C29—C30—C31	177.1 (4)	O2—N2—Co1—Cl1	88.8 (3)
C29—C30—C31—N11	0.7 (6)	C9—N5—Co1—N3	−42.2 (3)
C30—C29—C32—N12	162.2 (4)	C13—N5—Co1—N3	139.4 (3)
C28—C29—C32—N12	−20.7 (5)	C9—N5—Co1—N4	−123.7 (3)
C30—C29—C32—S2	−17.2 (5)	C13—N5—Co1—N4	57.8 (3)
C28—C29—C32—S2	159.9 (3)	C9—N5—Co1—N1	137.3 (3)
N12—C33—C34—C35	177.7 (4)	C13—N5—Co1—N1	−41.2 (3)
C33—C34—C35—C36	−176.5 (4)	C9—N5—Co1—N2	56.1 (3)
C2—C1—N1—O1	177.8 (3)	C13—N5—Co1—N2	−122.4 (3)
C5—C1—N1—O1	−2.9 (5)	C9—N5—Co1—Cl1	−122 (10)
C2—C1—N1—Co1	−2.8 (4)	C13—N5—Co1—Cl1	59 (10)
C5—C1—N1—Co1	176.5 (3)	C19—N7—Co2—N8	−2.8 (3)
C1—C2—N2—O2	−179.8 (3)	O5—N7—Co2—N8	177.8 (3)
C6—C2—N2—O2	−1.6 (5)	C19—N7—Co2—N9	178 (100)
C1—C2—N2—Co1	−1.1 (4)	O5—N7—Co2—N9	−2(14)
C6—C2—N2—Co1	177.1 (3)	C19—N7—Co2—N10	178.6 (3)
C4—C3—N3—O3	178.0 (3)	O5—N7—Co2—N10	−0.8 (3)
C7—C3—N3—O3	0.9 (7)	C19—N7—Co2—N11	87.4 (3)
C4—C3—N3—Co1	2.4 (5)	O5—N7—Co2—N11	−92.0 (3)
C7—C3—N3—Co1	−174.7 (4)	C19—N7—Co2—Cl2	−91.2 (3)
C3—C4—N4—O4	−178.7 (3)	O5—N7—Co2—Cl2	89.5 (3)
C8—C4—N4—O4	0.6 (6)	C20—N8—Co2—N7	1.8 (3)
C3—C4—N4—Co1	0.3 (4)	O6—N8—Co2—N7	−176.4 (3)
C8—C4—N4—Co1	179.6 (3)	C20—N8—Co2—N9	−178.2 (3)
C10—C9—N5—C13	2.1 (7)	O6—N8—Co2—N9	3.6 (3)
C10—C9—N5—Co1	−176.4 (4)	C20—N8—Co2—N10	121 (5)
C12—C13—N5—C9	−2.7 (6)	O6—N8—Co2—N10	−57 (5)
C12—C13—N5—Co1	175.9 (3)	C20—N8—Co2—N11	−88.0 (3)
C11—C14—N6—C15	−172.2 (5)	O6—N8—Co2—N11	93.8 (3)
S1—C14—N6—C15	5.6 (8)	C20—N8—Co2—Cl2	91.8 (3)
C16—C15—N6—C14	−86.9 (8)	O6—N8—Co2—Cl2	−86.4 (3)
C20—C19—N7—O5	−177.4 (3)	C21—N9—Co2—N7	−3(14)
C23—C19—N7—O5	1.4 (6)	O7—N9—Co2—N7	−180 (100)
C20—C19—N7—Co2	3.3 (4)	C21—N9—Co2—N8	178.0 (3)
C23—C19—N7—Co2	−177.9 (3)	O7—N9—Co2—N8	1.0 (3)
C19—C20—N8—O6	177.7 (3)	C21—N9—Co2—N10	−3.4 (3)
C24—C20—N8—O6	−0.9 (6)	O7—N9—Co2—N10	179.6 (3)
C19—C20—N8—Co2	−0.6 (4)	C21—N9—Co2—N11	87.8 (3)
C24—C20—N8—Co2	−179.2 (3)	O7—N9—Co2—N11	−89.2 (3)
C22—C21—N9—O7	−178.4 (3)	C21—N9—Co2—Cl2	−93.6 (3)
C25—C21—N9—O7	2.7 (6)	O7—N9—Co2—Cl2	89.3 (3)
C22—C21—N9—Co2	4.5 (4)	C22—N10—Co2—N7	−178.5 (3)
C25—C21—N9—Co2	−174.4 (3)	O8—N10—Co2—N7	3.6 (3)
C21—C22—N10—O8	178.3 (3)	C22—N10—Co2—N8	63 (5)
C26—C22—N10—O8	1.4 (6)	O8—N10—Co2—N8	−115 (5)
C21—C22—N10—Co2	0.4 (4)	C22—N10—Co2—N9	1.5 (3)
C26—C22—N10—Co2	−176.5 (3)	O8—N10—Co2—N9	−176.4 (3)
C28—C27—N11—C31	−0.2 (5)	C22—N10—Co2—N11	−88.5 (3)
C28—C27—N11—Co2	−179.9 (3)	O8—N10—Co2—N11	93.6 (3)
C30—C31—N11—C27	−0.4 (6)	C22—N10—Co2—Cl2	91.7 (3)
C30—C31—N11—Co2	179.2 (3)	O8—N10—Co2—Cl2	−86.2 (3)
C29—C32—N12—C33	175.5 (3)	C27—N11—Co2—N7	52.7 (3)
S2—C32—N12—C33	−5.2 (6)	C31—N11—Co2—N7	−126.9 (3)
C34—C33—N12—C32	−78.5 (5)	C27—N11—Co2—N8	134.7 (3)
C3—N3—Co1—N4	−1.8 (3)	C31—N11—Co2—N8	−44.9 (3)
O3—N3—Co1—N4	−177.4 (3)	C27—N11—Co2—N9	−126.7 (3)
C3—N3—Co1—N1	104 (3)	C31—N11—Co2—N9	53.7 (3)
O3—N3—Co1—N1	−72 (4)	C27—N11—Co2—N10	−46.1 (3)
C3—N3—Co1—N2	177.6 (3)	C31—N11—Co2—N10	134.3 (3)
O3—N3—Co1—N2	2.1 (3)	C27—N11—Co2—Cl2	127 (3)
C3—N3—Co1—N5	−91.8 (3)	C31—N11—Co2—Cl2	−52 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	1.20 (6)	1.32 (6)	2.491 (4)	162 (5)
O2—H2···O3	1.12 (6)	1.39 (6)	2.469 (4)	158 (5)
O8—H8···O5	1.17 (8)	1.34 (8)	2.486 (5)	165 (6)
O7—H7···O6	0.98 (7)	1.52 (7)	2.490 (5)	171 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4	1.20 (6)	1.32 (6)	2.491 (4)	162 (5)
O2—H2⋯O3	1.12 (6)	1.39 (6)	2.469 (4)	158 (5)
O8—H8⋯O5	1.17 (8)	1.34 (8)	2.486 (5)	165 (6)
O7—H7⋯O6	0.98 (7)	1.52 (7)	2.490 (5)	171 (7)