Chloridobis[diphenyl-glyoximato(1-)-κN,N'](1H-imidazole-κN)cobalt(III) hemihydrate.

The Co centre in the title compound, [Co(C(14)H(11)N(2)O(2))(2)Cl(C(3)H(4)N(2))]·0.5H(2)O, shows a slightly distorted octa-hedral coordination geometry. The glyoximate units of the mol-ecule are linked by O-H⋯O hydrogen bonds with the H atom almost in the middle of the two O atoms. The crystal packing is stabilized through inter-molecular N-H⋯O, N-H⋯N and O-H⋯Cl hydrogen bonds. The uncoordinated water mol-ecule shows half-occupation.

Related literature

For related literature, see: Calleri et al. (1967 ▶); Gupta et al. (2001 ▶, 2004 ▶); Lopez et al. (1991 ▶); Mandal & Gupta (2005 ▶); Silverstein & Bassler (1984 ▶); Toscano et al. (1983 ▶).

Experimental

Crystal data

[Co(C14H11N2O2)2Cl(C3H4N2)]·0.5H2O

M = 649.97

Orthorhombic,

a = 19.1004 (11) Å

b = 12.0462 (7) Å

c = 26.9627 (18) Å

V = 6203.8 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.69 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.732, T max = 0.850

28473 measured reflections

5282 independent reflections

3705 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.104

S = 1.06

5282 reflections

415 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680804347X/bt2831sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804347X/bt2831Isup2.hkl

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

[Co(C14H11N2O2)2Cl(C3H4N2)]·0.5H2O	Dx = 1.392 Mg m−3
Mr = 649.97	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 5466 reflections
a = 19.1004 (11) Å	θ = 2.1–24.9°
b = 12.0462 (7) Å	µ = 0.69 mm−1
c = 26.9627 (18) Å	T = 293 K
V = 6203.8 (7) Å3	Needle, brown
Z = 8	0.30 × 0.20 × 0.20 mm
F(000) = 2680

Bruker Kappa APEXII CCD diffractometer	5282 independent reflections
Radiation source: fine-focus sealed tube	3705 reflections with I > 2σ(I)
graphite	Rint = 0.051
ω and φ scans	θmax = 24.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −20→22
Tmin = 0.732, Tmax = 0.850	k = −14→13
28473 measured reflections	l = −31→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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0434P)2 + 2.9454P] where P = (Fo2 + 2Fc2)/3
5282 reflections	(Δ/σ)max = 0.001
415 parameters	Δρmax = 0.35 e Å−3
3 restraints	Δρmin = −0.26 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 > 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	0.63561 (15)	0.1880 (3)	0.00280 (11)	0.0409 (7)
C2	0.70947 (14)	0.1624 (2)	0.01198 (11)	0.0381 (7)
C3	0.60509 (15)	0.2080 (3)	−0.04659 (11)	0.0464 (8)
C4	0.56950 (19)	0.3038 (3)	−0.05731 (13)	0.0639 (10)
H4	0.5658	0.3596	−0.0336	0.077*
C5	0.5390 (2)	0.3174 (4)	−0.10368 (17)	0.0861 (14)
H5	0.5154	0.3827	−0.1114	0.103*
C6	0.5438 (2)	0.2339 (5)	−0.13802 (16)	0.0882 (15)
H6	0.5224	0.2427	−0.1688	0.106*
C7	0.5790 (2)	0.1389 (5)	−0.12817 (15)	0.0837 (13)
H7	0.5823	0.0832	−0.1520	0.100*
C8	0.61007 (18)	0.1258 (3)	−0.08218 (13)	0.0624 (10)
H8	0.6346	0.0610	−0.0751	0.075*
C9	0.76536 (15)	0.1743 (3)	−0.02548 (10)	0.0406 (7)
C10	0.76866 (18)	0.2672 (3)	−0.05512 (12)	0.0575 (9)
H10	0.7342	0.3215	−0.0526	0.069*
C11	0.8230 (2)	0.2803 (4)	−0.08864 (14)	0.0707 (11)
H11	0.8251	0.3434	−0.1084	0.085*
C12	0.8733 (2)	0.2007 (4)	−0.09260 (14)	0.0701 (11)
H12	0.9094	0.2094	−0.1154	0.084*
C13	0.87115 (19)	0.1089 (4)	−0.06346 (14)	0.0664 (11)
H13	0.9060	0.0554	−0.0660	0.080*
C14	0.81727 (17)	0.0953 (3)	−0.03009 (12)	0.0529 (9)
H14	0.8158	0.0320	−0.0104	0.064*
C15	0.57331 (14)	0.0802 (2)	0.18684 (11)	0.0364 (7)
C16	0.64821 (14)	0.0580 (2)	0.19665 (10)	0.0365 (7)
C17	0.51700 (14)	0.0551 (3)	0.22257 (11)	0.0402 (7)
C18	0.46087 (16)	0.1271 (3)	0.22873 (13)	0.0550 (9)
H18	0.4589	0.1930	0.2108	0.066*
C19	0.40809 (19)	0.1009 (4)	0.26147 (15)	0.0737 (12)
H19	0.3707	0.1495	0.2657	0.088*
C20	0.41012 (19)	0.0049 (4)	0.28760 (15)	0.0781 (13)
H20	0.3743	−0.0119	0.3097	0.094*
C21	0.46428 (19)	−0.0669 (4)	0.28165 (15)	0.0758 (12)
H21	0.4651	−0.1331	0.2993	0.091*
C22	0.51801 (17)	−0.0419 (3)	0.24951 (12)	0.0554 (9)
H22	0.5553	−0.0909	0.2460	0.067*
C23	0.67758 (14)	0.0249 (3)	0.24497 (11)	0.0434 (8)
C24	0.66383 (18)	0.0875 (3)	0.28642 (13)	0.0623 (10)
H24	0.6353	0.1499	0.2840	0.075*
C25	0.6919 (2)	0.0584 (5)	0.33133 (14)	0.0855 (14)
H25	0.6824	0.1008	0.3594	0.103*
C26	0.7334 (2)	−0.0319 (5)	0.33480 (17)	0.0930 (16)
H26	0.7528	−0.0507	0.3653	0.112*
C27	0.7473 (2)	−0.0954 (4)	0.29465 (17)	0.0851 (14)
H27	0.7752	−0.1582	0.2978	0.102*
C28	0.71984 (18)	−0.0669 (3)	0.24888 (14)	0.0660 (10)
H28	0.7299	−0.1096	0.2210	0.079*
C29	0.57488 (16)	−0.0595 (3)	0.04757 (12)	0.0548 (9)
H29	0.5386	−0.0170	0.0346	0.066*
C30	0.58509 (18)	−0.1672 (3)	0.03882 (13)	0.0593 (9)
H30	0.5582	−0.2130	0.0187	0.071*
C31	0.66589 (16)	−0.1065 (3)	0.08821 (12)	0.0488 (8)
H31	0.7053	−0.1042	0.1084	0.059*
N1	0.59804 (12)	0.1815 (2)	0.04272 (9)	0.0426 (6)
N2	0.72105 (11)	0.13202 (19)	0.05738 (9)	0.0361 (6)
N3	0.56368 (11)	0.1196 (2)	0.14284 (9)	0.0383 (6)
N4	0.68677 (11)	0.0763 (2)	0.15816 (8)	0.0382 (6)
N5	0.62594 (11)	−0.0215 (2)	0.07856 (9)	0.0380 (6)
N6	0.64288 (15)	−0.1966 (3)	0.06536 (11)	0.0552 (7)
O1	0.52933 (10)	0.1998 (2)	0.04167 (8)	0.0542 (6)
O2	0.78462 (9)	0.10740 (17)	0.07404 (7)	0.0425 (5)
O3	0.49944 (10)	0.14234 (19)	0.12648 (8)	0.0520 (6)
O4	0.75702 (10)	0.0645 (2)	0.16194 (8)	0.0496 (6)
O5	0.5658 (4)	0.4699 (6)	0.0555 (3)	0.127 (2)	0.50
H5B	0.611 (2)	0.438 (7)	0.055 (4)	0.152*	0.50
H5A	0.535 (4)	0.425 (7)	0.074 (4)	0.152*	0.50
Co1	0.642761 (18)	0.12847 (3)	0.100084 (14)	0.03524 (13)
Cl1	0.66393 (4)	0.30158 (7)	0.12458 (3)	0.0560 (2)
H2	0.7759 (17)	0.087 (3)	0.1270 (14)	0.070 (11)*
H3	0.509 (2)	0.169 (4)	0.0893 (17)	0.106 (15)*
H6A	0.6632 (18)	−0.272 (3)	0.0650 (13)	0.075 (12)*

	U11	U22	U33	U12	U13	U23
C1	0.0429 (17)	0.0496 (19)	0.0303 (18)	−0.0003 (14)	0.0007 (14)	0.0066 (14)
C2	0.0378 (16)	0.0466 (18)	0.0301 (18)	−0.0019 (13)	0.0026 (13)	0.0013 (13)
C3	0.0405 (17)	0.065 (2)	0.0334 (19)	−0.0075 (16)	0.0008 (14)	0.0093 (16)
C4	0.074 (2)	0.067 (3)	0.050 (2)	−0.002 (2)	−0.0123 (19)	0.0156 (19)
C5	0.082 (3)	0.102 (4)	0.075 (3)	−0.002 (3)	−0.020 (2)	0.043 (3)
C6	0.080 (3)	0.138 (5)	0.046 (3)	−0.030 (3)	−0.014 (2)	0.015 (3)
C7	0.075 (3)	0.131 (4)	0.045 (3)	−0.014 (3)	−0.003 (2)	−0.012 (3)
C8	0.055 (2)	0.089 (3)	0.043 (2)	0.0001 (19)	0.0009 (17)	−0.003 (2)
C9	0.0409 (16)	0.0508 (19)	0.0301 (17)	−0.0089 (15)	0.0017 (13)	−0.0025 (15)
C10	0.058 (2)	0.066 (2)	0.048 (2)	−0.0061 (18)	0.0019 (17)	0.0103 (18)
C11	0.080 (3)	0.080 (3)	0.052 (3)	−0.028 (2)	0.011 (2)	0.013 (2)
C12	0.059 (2)	0.100 (3)	0.052 (3)	−0.027 (2)	0.0202 (19)	−0.009 (2)
C13	0.058 (2)	0.084 (3)	0.057 (3)	−0.001 (2)	0.0203 (19)	−0.011 (2)
C14	0.059 (2)	0.058 (2)	0.042 (2)	−0.0033 (17)	0.0129 (16)	−0.0043 (16)
C15	0.0348 (15)	0.0451 (18)	0.0293 (17)	0.0025 (13)	0.0024 (12)	0.0010 (13)
C16	0.0341 (15)	0.0463 (18)	0.0293 (17)	0.0019 (13)	0.0021 (13)	−0.0015 (13)
C17	0.0342 (16)	0.054 (2)	0.0329 (17)	0.0007 (14)	0.0046 (13)	0.0020 (15)
C18	0.0485 (19)	0.060 (2)	0.057 (2)	0.0096 (17)	0.0165 (16)	0.0085 (17)
C19	0.054 (2)	0.090 (3)	0.078 (3)	0.019 (2)	0.031 (2)	0.012 (2)
C20	0.057 (2)	0.100 (3)	0.077 (3)	0.007 (2)	0.034 (2)	0.029 (3)
C21	0.061 (2)	0.085 (3)	0.082 (3)	0.006 (2)	0.028 (2)	0.033 (2)
C22	0.0460 (19)	0.063 (2)	0.057 (2)	0.0088 (16)	0.0122 (16)	0.0135 (19)
C23	0.0312 (15)	0.070 (2)	0.0294 (18)	0.0010 (15)	−0.0004 (13)	0.0039 (15)
C24	0.062 (2)	0.088 (3)	0.038 (2)	0.0011 (19)	−0.0025 (17)	−0.0001 (19)
C25	0.079 (3)	0.142 (4)	0.035 (2)	0.002 (3)	−0.011 (2)	−0.002 (2)
C26	0.069 (3)	0.161 (5)	0.049 (3)	−0.001 (3)	−0.014 (2)	0.037 (3)
C27	0.068 (3)	0.120 (4)	0.068 (3)	0.028 (2)	−0.005 (2)	0.036 (3)
C28	0.057 (2)	0.088 (3)	0.053 (2)	0.016 (2)	0.0057 (18)	0.015 (2)
C29	0.0425 (19)	0.067 (3)	0.054 (2)	−0.0026 (17)	−0.0135 (16)	0.0037 (18)
C30	0.057 (2)	0.063 (3)	0.057 (2)	−0.0122 (18)	−0.0107 (18)	−0.0093 (19)
C31	0.0416 (17)	0.058 (2)	0.047 (2)	0.0045 (16)	−0.0048 (15)	−0.0061 (16)
N1	0.0347 (13)	0.0580 (17)	0.0350 (15)	0.0065 (12)	−0.0001 (11)	0.0056 (12)
N2	0.0299 (12)	0.0463 (14)	0.0320 (14)	−0.0004 (11)	0.0003 (10)	−0.0002 (11)
N3	0.0294 (12)	0.0527 (15)	0.0330 (15)	0.0063 (11)	0.0025 (10)	0.0035 (12)
N4	0.0280 (12)	0.0570 (16)	0.0295 (14)	0.0033 (11)	−0.0008 (10)	−0.0025 (11)
N5	0.0324 (12)	0.0502 (15)	0.0316 (14)	0.0044 (11)	−0.0007 (11)	0.0012 (12)
N6	0.0563 (18)	0.0526 (19)	0.057 (2)	0.0056 (15)	0.0025 (14)	−0.0056 (15)
O1	0.0346 (11)	0.0849 (17)	0.0429 (14)	0.0141 (11)	−0.0007 (10)	0.0164 (12)
O2	0.0293 (10)	0.0635 (14)	0.0347 (12)	0.0020 (9)	0.0022 (9)	0.0051 (10)
O3	0.0279 (10)	0.0848 (17)	0.0432 (14)	0.0143 (10)	0.0013 (9)	0.0154 (12)
O4	0.0258 (10)	0.0886 (17)	0.0343 (13)	0.0043 (10)	0.0010 (9)	0.0078 (12)
O5	0.144 (7)	0.109 (6)	0.127 (7)	0.037 (5)	0.001 (5)	0.011 (4)
Co1	0.0288 (2)	0.0490 (2)	0.0280 (2)	0.00340 (18)	0.00147 (16)	0.00213 (18)
Cl1	0.0571 (5)	0.0530 (5)	0.0580 (6)	−0.0016 (4)	0.0119 (4)	−0.0087 (4)

C1—N1	1.296 (4)	C21—C22	1.376 (4)
C1—C2	1.465 (4)	C21—H21	0.9300
C1—C3	1.473 (4)	C22—H22	0.9300
C2—N2	1.296 (3)	C23—C28	1.373 (5)
C2—C9	1.477 (4)	C23—C24	1.374 (5)
C3—C4	1.370 (5)	C24—C25	1.370 (5)
C3—C8	1.382 (5)	C24—H24	0.9300
C4—C5	1.389 (5)	C25—C26	1.348 (6)
C4—H4	0.9300	C25—H25	0.9300
C5—C6	1.370 (6)	C26—C27	1.352 (6)
C5—H5	0.9300	C26—H26	0.9300
C6—C7	1.354 (6)	C27—C28	1.384 (5)
C6—H6	0.9300	C27—H27	0.9300
C7—C8	1.384 (5)	C28—H28	0.9300
C7—H7	0.9300	C29—C30	1.333 (5)
C8—H8	0.9300	C29—N5	1.364 (4)
C9—C10	1.377 (4)	C29—H29	0.9300
C9—C14	1.380 (4)	C30—N6	1.362 (4)
C10—C11	1.385 (5)	C30—H30	0.9300
C10—H10	0.9300	C31—N5	1.304 (4)
C11—C12	1.362 (6)	C31—N6	1.324 (4)
C11—H11	0.9300	C31—H31	0.9300
C12—C13	1.357 (5)	N1—O1	1.331 (3)
C12—H12	0.9300	N1—Co1	1.879 (2)
C13—C14	1.377 (5)	N2—O2	1.328 (3)
C13—H13	0.9300	N2—Co1	1.888 (2)
C14—H14	0.9300	N3—O3	1.332 (3)
C15—N3	1.291 (3)	N3—Co1	1.903 (2)
C15—C17	1.475 (4)	N4—O4	1.353 (3)
C15—C16	1.479 (4)	N4—Co1	1.885 (2)
C16—N4	1.291 (3)	N5—Co1	1.924 (2)
C16—C23	1.474 (4)	N6—H6A	0.98 (4)
C17—C22	1.376 (4)	O1—H3	1.39 (5)
C17—C18	1.389 (4)	O2—H2	1.46 (4)
C18—C19	1.377 (4)	O3—H3	1.07 (5)
C18—H18	0.9300	O4—H2	1.05 (4)
C19—C20	1.355 (5)	O5—H5B	0.946 (10)
C19—H19	0.9300	O5—H5A	0.946 (10)
C20—C21	1.358 (5)	Co1—Cl1	2.2244 (9)
C20—H20	0.9300
N1—C1—C2	112.3 (3)	C28—C23—C24	119.5 (3)
N1—C1—C3	122.8 (3)	C28—C23—C16	120.7 (3)
C2—C1—C3	124.6 (3)	C24—C23—C16	119.8 (3)
N2—C2—C1	112.5 (2)	C25—C24—C23	120.2 (4)
N2—C2—C9	123.4 (3)	C25—C24—H24	119.9
C1—C2—C9	124.0 (3)	C23—C24—H24	119.9
C4—C3—C8	119.4 (3)	C26—C25—C24	119.9 (4)
C4—C3—C1	121.6 (3)	C26—C25—H25	120.1
C8—C3—C1	118.9 (3)	C24—C25—H25	120.1
C3—C4—C5	119.8 (4)	C25—C26—C27	121.0 (4)
C3—C4—H4	120.1	C25—C26—H26	119.5
C5—C4—H4	120.1	C27—C26—H26	119.5
C6—C5—C4	119.6 (4)	C26—C27—C28	120.0 (4)
C6—C5—H5	120.2	C26—C27—H27	120.0
C4—C5—H5	120.2	C28—C27—H27	120.0
C7—C6—C5	121.4 (4)	C23—C28—C27	119.4 (4)
C7—C6—H6	119.3	C23—C28—H28	120.3
C5—C6—H6	119.3	C27—C28—H28	120.3
C6—C7—C8	119.0 (4)	C30—C29—N5	109.3 (3)
C6—C7—H7	120.5	C30—C29—H29	125.3
C8—C7—H7	120.5	N5—C29—H29	125.3
C3—C8—C7	120.7 (4)	C29—C30—N6	106.2 (3)
C3—C8—H8	119.6	C29—C30—H30	126.9
C7—C8—H8	119.6	N6—C30—H30	126.9
C10—C9—C14	118.4 (3)	N5—C31—N6	110.9 (3)
C10—C9—C2	120.6 (3)	N5—C31—H31	124.5
C14—C9—C2	120.9 (3)	N6—C31—H31	124.5
C9—C10—C11	120.4 (4)	C1—N1—O1	121.2 (2)
C9—C10—H10	119.8	C1—N1—Co1	116.91 (19)
C11—C10—H10	119.8	O1—N1—Co1	121.47 (18)
C12—C11—C10	120.0 (4)	C2—N2—O2	122.6 (2)
C12—C11—H11	120.0	C2—N2—Co1	116.56 (19)
C10—C11—H11	120.0	O2—N2—Co1	120.84 (17)
C13—C12—C11	120.5 (3)	C15—N3—O3	120.7 (2)
C13—C12—H12	119.8	C15—N3—Co1	117.66 (18)
C11—C12—H12	119.8	O3—N3—Co1	121.26 (18)
C12—C13—C14	119.9 (4)	C16—N4—O4	119.1 (2)
C12—C13—H13	120.1	C16—N4—Co1	118.04 (19)
C14—C13—H13	120.1	O4—N4—Co1	122.67 (17)
C13—C14—C9	120.9 (3)	C31—N5—C29	106.1 (3)
C13—C14—H14	119.6	C31—N5—Co1	125.4 (2)
C9—C14—H14	119.6	C29—N5—Co1	128.3 (2)
N3—C15—C17	124.9 (2)	C31—N6—C30	107.5 (3)
N3—C15—C16	111.6 (2)	C31—N6—H6A	129 (2)
C17—C15—C16	123.5 (3)	C30—N6—H6A	124 (2)
N4—C16—C23	122.7 (2)	N1—O1—H3	101.9 (17)
N4—C16—C15	112.2 (2)	N2—O2—H2	105.3 (13)
C23—C16—C15	125.1 (2)	N3—O3—H3	102 (2)
C22—C17—C18	118.6 (3)	N4—O4—H2	104.2 (18)
C22—C17—C15	120.6 (3)	H5B—O5—H5A	110.0 (17)
C18—C17—C15	120.9 (3)	N1—Co1—N4	179.23 (11)
C19—C18—C17	119.9 (3)	N1—Co1—N2	81.39 (10)
C19—C18—H18	120.0	N4—Co1—N2	99.27 (10)
C17—C18—H18	120.0	N1—Co1—N3	99.02 (10)
C20—C19—C18	120.6 (3)	N4—Co1—N3	80.33 (10)
C20—C19—H19	119.7	N2—Co1—N3	178.07 (10)
C18—C19—H19	119.7	N1—Co1—N5	89.71 (11)
C19—C20—C21	120.3 (3)	N4—Co1—N5	90.69 (10)
C19—C20—H20	119.9	N2—Co1—N5	88.25 (10)
C21—C20—H20	119.9	N3—Co1—N5	89.86 (10)
C20—C21—C22	120.2 (4)	N1—Co1—Cl1	90.47 (8)
C20—C21—H21	119.9	N4—Co1—Cl1	89.13 (8)
C22—C21—H21	119.9	N2—Co1—Cl1	90.91 (7)
C17—C22—C21	120.5 (3)	N3—Co1—Cl1	90.97 (8)
C17—C22—H22	119.8	N5—Co1—Cl1	179.11 (7)
C21—C22—H22	119.8
N1—C1—C2—N2	4.0 (4)	C17—C15—N3—O3	0.9 (4)
C3—C1—C2—N2	−170.2 (3)	C16—C15—N3—O3	178.3 (2)
N1—C1—C2—C9	−173.5 (3)	C17—C15—N3—Co1	−172.4 (2)
C3—C1—C2—C9	12.3 (5)	C16—C15—N3—Co1	5.0 (3)
N1—C1—C3—C4	62.3 (4)	C23—C16—N4—O4	0.2 (4)
C2—C1—C3—C4	−124.1 (4)	C15—C16—N4—O4	177.1 (2)
N1—C1—C3—C8	−114.9 (4)	C23—C16—N4—Co1	−175.5 (2)
C2—C1—C3—C8	58.7 (4)	C15—C16—N4—Co1	1.4 (3)
C8—C3—C4—C5	−0.1 (5)	N6—C31—N5—C29	−0.4 (4)
C1—C3—C4—C5	−177.3 (3)	N6—C31—N5—Co1	−175.6 (2)
C3—C4—C5—C6	1.1 (6)	C30—C29—N5—C31	−0.3 (4)
C4—C5—C6—C7	−1.4 (7)	C30—C29—N5—Co1	174.7 (2)
C5—C6—C7—C8	0.7 (7)	N5—C31—N6—C30	0.9 (4)
C4—C3—C8—C7	−0.6 (5)	C29—C30—N6—C31	−1.0 (4)
C1—C3—C8—C7	176.6 (3)	C1—N1—Co1—N4	154 (9)
C6—C7—C8—C3	0.3 (6)	O1—N1—Co1—N4	−33 (9)
N2—C2—C9—C10	−132.9 (3)	C1—N1—Co1—N2	4.7 (2)
C1—C2—C9—C10	44.3 (4)	O1—N1—Co1—N2	177.4 (2)
N2—C2—C9—C14	44.1 (4)	C1—N1—Co1—N3	−173.4 (2)
C1—C2—C9—C14	−138.7 (3)	O1—N1—Co1—N3	−0.7 (2)
C14—C9—C10—C11	0.0 (5)	C1—N1—Co1—N5	−83.6 (2)
C2—C9—C10—C11	177.1 (3)	O1—N1—Co1—N5	89.1 (2)
C9—C10—C11—C12	0.3 (6)	C1—N1—Co1—Cl1	95.5 (2)
C10—C11—C12—C13	−0.8 (6)	O1—N1—Co1—Cl1	−91.7 (2)
C11—C12—C13—C14	0.9 (6)	C16—N4—Co1—N1	33 (9)
C12—C13—C14—C9	−0.5 (6)	O4—N4—Co1—N1	−142 (9)
C10—C9—C14—C13	0.1 (5)	C16—N4—Co1—N2	−177.2 (2)
C2—C9—C14—C13	−177.0 (3)	O4—N4—Co1—N2	7.3 (2)
N3—C15—C16—N4	−4.0 (4)	C16—N4—Co1—N3	0.9 (2)
C17—C15—C16—N4	173.4 (3)	O4—N4—Co1—N3	−174.6 (2)
N3—C15—C16—C23	172.8 (3)	C16—N4—Co1—N5	−88.8 (2)
C17—C15—C16—C23	−9.8 (5)	O4—N4—Co1—N5	95.6 (2)
N3—C15—C17—C22	136.0 (3)	C16—N4—Co1—Cl1	92.1 (2)
C16—C15—C17—C22	−41.1 (4)	O4—N4—Co1—Cl1	−83.5 (2)
N3—C15—C17—C18	−42.1 (5)	C2—N2—Co1—N1	−2.2 (2)
C16—C15—C17—C18	140.8 (3)	O2—N2—Co1—N1	176.0 (2)
C22—C17—C18—C19	0.4 (5)	C2—N2—Co1—N4	178.2 (2)
C15—C17—C18—C19	178.5 (3)	O2—N2—Co1—N4	−3.6 (2)
C17—C18—C19—C20	−0.4 (6)	C2—N2—Co1—N3	100 (3)
C18—C19—C20—C21	−0.2 (7)	O2—N2—Co1—N3	−82 (3)
C19—C20—C21—C22	0.9 (7)	C2—N2—Co1—N5	87.8 (2)
C18—C17—C22—C21	0.3 (5)	O2—N2—Co1—N5	−94.1 (2)
C15—C17—C22—C21	−177.9 (3)	C2—N2—Co1—Cl1	−92.5 (2)
C20—C21—C22—C17	−0.9 (6)	O2—N2—Co1—Cl1	85.63 (19)
N4—C16—C23—C28	−55.4 (4)	C15—N3—Co1—N1	176.9 (2)
C15—C16—C23—C28	128.1 (3)	O3—N3—Co1—N1	3.7 (2)
N4—C16—C23—C24	123.3 (3)	C15—N3—Co1—N4	−3.5 (2)
C15—C16—C23—C24	−53.2 (4)	O3—N3—Co1—N4	−176.7 (2)
C28—C23—C24—C25	−0.2 (5)	C15—N3—Co1—N2	75 (3)
C16—C23—C24—C25	−178.8 (3)	O3—N3—Co1—N2	−99 (3)
C23—C24—C25—C26	0.2 (6)	C15—N3—Co1—N5	87.2 (2)
C24—C25—C26—C27	−0.8 (7)	O3—N3—Co1—N5	−86.0 (2)
C25—C26—C27—C28	1.3 (7)	C15—N3—Co1—Cl1	−92.4 (2)
C24—C23—C28—C27	0.7 (5)	O3—N3—Co1—Cl1	94.3 (2)
C16—C23—C28—C27	179.3 (3)	C31—N5—Co1—N1	149.3 (3)
C26—C27—C28—C23	−1.2 (6)	C29—N5—Co1—N1	−24.8 (3)
N5—C29—C30—N6	0.8 (4)	C31—N5—Co1—N4	−31.4 (3)
C2—C1—N1—O1	−178.7 (3)	C29—N5—Co1—N4	154.5 (3)
C3—C1—N1—O1	−4.4 (5)	C31—N5—Co1—N2	67.9 (3)
C2—C1—N1—Co1	−5.9 (3)	C29—N5—Co1—N2	−106.2 (3)
C3—C1—N1—Co1	168.4 (2)	C31—N5—Co1—N3	−111.7 (3)
C1—C2—N2—O2	−178.4 (2)	C29—N5—Co1—N3	74.2 (3)
C9—C2—N2—O2	−0.9 (4)	C31—N5—Co1—Cl1	47 (5)
C1—C2—N2—Co1	−0.3 (3)	C29—N5—Co1—Cl1	−127 (5)
C9—C2—N2—Co1	177.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H2···O2	1.05 (4)	1.46 (4)	2.482 (3)	165 (3)
O3—H3···O1	1.07 (5)	1.39 (5)	2.456 (3)	174 (4)
N6—H6A···O2i	0.98 (4)	1.78 (4)	2.747 (4)	166 (3)
N6—H6A···N2i	0.98 (4)	2.50 (4)	3.326 (4)	141 (3)
O5—H5B···Cl1	0.95 (1)	2.69 (8)	3.331 (7)	126 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H2⋯O2	1.05 (4)	1.46 (4)	2.482 (3)	165 (3)
O3—H3⋯O1	1.07 (5)	1.39 (5)	2.456 (3)	174 (4)
N6—H6A⋯O2i	0.98 (4)	1.78 (4)	2.747 (4)	166 (3)
N6—H6A⋯N2i	0.98 (4)	2.50 (4)	3.326 (4)	141 (3)
O5—H5B⋯Cl1	0.946 (10)	2.69 (8)	3.331 (7)	126 (7)

Symmetry code: (i) .