Diaqua-bis-[2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinato]cobalt(II).

In the title complex, [Co(C(13)H(14)N(3)O(3))(2)(H(2)O)(2)], the Co(II) atom has a distorted octa-hedral coordination, formed by four N atoms from two (±)-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinate ligands and two O atoms from two water mol-ecules. Intra-molecular N-H⋯O and O-H⋯O hydrogen bonds are present. In the crystal, inter-molecular O-H⋯O hydrogen bonds link the complex mol-ecules into a chain along [010].

Related literature

For the synthesis and structures of the compounds containing imidazolidinone derivatives, see: Bombek et al. (2005 ▶); Ellis et al. (2000 ▶); Erre et al. (1998 ▶); Fu et al. (2008 ▶). For coordination compounds with pyridine­carb­oxy­lic acids, see: Chatterjee et al. (1998 ▶); Nathan & Mai (2000 ▶); Park et al. (2007 ▶); Yang et al. (2002 ▶).

Experimental

Crystal data

[Co(C13H14N3O3)2(H2O)2]

M = 615.51

Orthorhombic,

a = 12.548 (5) Å

b = 19.558 (8) Å

c = 23.07 (1) Å

V = 5662 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.67 mm−1

T = 298 K

0.43 × 0.42 × 0.40 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.763, T max = 0.777

24468 measured reflections

4992 independent reflections

2623 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.142

S = 1.03

4992 reflections

376 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810044715/hy2369sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044715/hy2369Isup2.hkl

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

[Co(C13H14N3O3)2(H2O)2]	F(000) = 2568
Mr = 615.51	Dx = 1.444 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1647 reflections
a = 12.548 (5) Å	θ = 2.3–19.4°
b = 19.558 (8) Å	µ = 0.67 mm−1
c = 23.07 (1) Å	T = 298 K
V = 5662 (4) Å3	Block, red
Z = 8	0.43 × 0.42 × 0.40 mm

Bruker APEX CCD diffractometer	4992 independent reflections
Radiation source: fine-focus sealed tube	2623 reflections with I > 2σ(I)
graphite	Rint = 0.081
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.763, Tmax = 0.777	k = −23→20
24468 measured reflections	l = −27→19

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0582P)2] where P = (Fo2 + 2Fc2)/3
4992 reflections	(Δ/σ)max = 0.001
376 parameters	Δρmax = 0.73 e Å−3
2 restraints	Δρmin = −0.41 e Å−3

	x	y	z	Uiso*/Ueq
Co1	0.27194 (5)	0.10887 (3)	0.37482 (2)	0.03099 (19)
N1	0.1586 (3)	0.18733 (17)	0.39738 (15)	0.0385 (9)
N2	0.2182 (3)	0.26551 (19)	0.26096 (15)	0.0527 (11)
H2	0.1887	0.3050	0.2577	0.063*
N3	0.2662 (3)	0.16654 (18)	0.30244 (14)	0.0383 (9)
N4	0.1631 (3)	0.02982 (17)	0.34952 (15)	0.0378 (9)
N5	0.2214 (4)	−0.0503 (2)	0.48558 (16)	0.0639 (13)
H5	0.1931	−0.0902	0.4882	0.077*
N6	0.2623 (3)	0.05068 (18)	0.44694 (15)	0.0382 (9)
O1	0.0968 (3)	0.42292 (16)	0.37455 (14)	0.0643 (10)
O2	0.1192 (3)	0.37261 (16)	0.28991 (15)	0.0658 (11)
O3	0.3576 (3)	0.11596 (18)	0.22656 (14)	0.0684 (11)
O4	0.1007 (3)	−0.20607 (16)	0.37274 (14)	0.0655 (10)
O5	0.1140 (4)	−0.15460 (19)	0.45612 (16)	0.0958 (16)
O6	0.3491 (3)	0.10220 (17)	0.52340 (13)	0.0658 (11)
O7	0.3937 (2)	0.05098 (15)	0.33722 (13)	0.0502 (9)
H7A	0.3886	0.0555	0.3007	0.060*
H7B	0.3991	0.0085	0.3446	0.060*
O8	0.3882 (2)	0.16846 (14)	0.41510 (12)	0.0480 (9)
H8A	0.3785	0.1661	0.4515	0.058*
H8B	0.3928	0.2103	0.4055	0.058*
C1	0.1092 (4)	0.3720 (2)	0.3438 (2)	0.0420 (12)
C2	0.1581 (4)	0.2430 (2)	0.36198 (18)	0.0354 (12)
C3	0.1090 (3)	0.3042 (2)	0.37691 (18)	0.0356 (11)
C4	0.0523 (4)	0.3037 (2)	0.4295 (2)	0.0482 (13)
H4	0.0173	0.3431	0.4414	0.058*
C5	0.0476 (4)	0.2467 (2)	0.4633 (2)	0.0592 (15)
H5A	0.0074	0.2462	0.4972	0.071*
C6	0.1035 (4)	0.1901 (2)	0.4461 (2)	0.0534 (14)
H6	0.1027	0.1517	0.4699	0.064*
C7	0.2153 (4)	0.2272 (2)	0.30712 (18)	0.0387 (11)
C8	0.3064 (4)	0.1638 (2)	0.2472 (2)	0.0507 (13)
C9	0.2802 (5)	0.2306 (3)	0.2150 (2)	0.0572 (13)
C10	0.3847 (4)	0.2701 (3)	0.2021 (2)	0.0756 (17)
H10A	0.3681	0.3163	0.1913	0.113*
H10B	0.4221	0.2481	0.1709	0.113*
H10C	0.4288	0.2703	0.2361	0.113*
C11	0.2169 (5)	0.2188 (3)	0.1624 (2)	0.0691 (16)
H11	0.2597	0.1894	0.1371	0.083*
C12	0.1139 (4)	0.1788 (3)	0.1769 (2)	0.0757 (18)
H12A	0.1310	0.1405	0.2012	0.114*
H12B	0.0817	0.1628	0.1417	0.114*
H12C	0.0650	0.2084	0.1969	0.114*
C13	0.1922 (6)	0.2838 (3)	0.1280 (2)	0.113 (3)
H13A	0.1501	0.2724	0.0947	0.170*
H13B	0.2577	0.3047	0.1157	0.170*
H13C	0.1534	0.3152	0.1521	0.170*
C14	0.1105 (4)	−0.1549 (2)	0.4027 (2)	0.0467 (13)
C15	0.1611 (3)	−0.0258 (2)	0.38519 (18)	0.0367 (11)
C16	0.1138 (4)	−0.0873 (2)	0.36856 (18)	0.0369 (11)
C17	0.0633 (4)	−0.0885 (2)	0.3139 (2)	0.0486 (13)
H17	0.0308	−0.1284	0.3009	0.058*
C18	0.0619 (4)	−0.0317 (2)	0.2801 (2)	0.0505 (14)
H18	0.0264	−0.0320	0.2447	0.061*
C19	0.1136 (4)	0.0263 (2)	0.2988 (2)	0.0509 (14)
H19	0.1139	0.0646	0.2749	0.061*
C20	0.2145 (4)	−0.0108 (2)	0.44084 (18)	0.0418 (12)
C21	0.3021 (4)	0.0531 (3)	0.5021 (2)	0.0515 (14)
C22	0.2846 (5)	−0.0172 (3)	0.5315 (2)	0.0660 (15)
C23	0.3951 (5)	−0.0554 (3)	0.5391 (2)	0.0811 (18)
H23A	0.3830	−0.1004	0.5543	0.122*
H23B	0.4394	−0.0301	0.5654	0.122*
H23C	0.4299	−0.0587	0.5021	0.122*
C24	0.2291 (6)	−0.0174 (4)	0.5862 (3)	0.094 (2)
H24	0.2137	−0.0650	0.5966	0.113*
C25	0.2912 (6)	0.0155 (3)	0.6367 (2)	0.113 (3)
H25A	0.3569	−0.0087	0.6425	0.169*
H25B	0.2492	0.0134	0.6714	0.169*
H25C	0.3063	0.0624	0.6275	0.169*
C26	0.1250 (6)	0.0190 (4)	0.5779 (3)	0.111 (3)
H26A	0.1376	0.0673	0.5751	0.167*
H26B	0.0792	0.0100	0.6104	0.167*
H26C	0.0916	0.0031	0.5430	0.167*

	U11	U22	U33	U12	U13	U23
Co1	0.0399 (3)	0.0183 (3)	0.0348 (3)	−0.0004 (3)	0.0002 (3)	0.0031 (2)
N1	0.044 (2)	0.030 (2)	0.042 (2)	0.0002 (18)	0.0040 (18)	0.0034 (17)
N2	0.079 (3)	0.036 (2)	0.043 (3)	0.020 (2)	0.005 (2)	0.008 (2)
N3	0.051 (2)	0.025 (2)	0.039 (2)	0.0067 (19)	0.0055 (18)	0.0026 (16)
N4	0.045 (3)	0.030 (2)	0.039 (2)	−0.0040 (18)	−0.0031 (19)	0.0024 (17)
N5	0.100 (4)	0.048 (3)	0.044 (3)	−0.034 (3)	−0.010 (2)	0.012 (2)
N6	0.053 (3)	0.025 (2)	0.037 (2)	−0.0035 (19)	−0.0028 (18)	0.0012 (16)
O1	0.100 (3)	0.0241 (19)	0.069 (2)	−0.0034 (19)	0.015 (2)	−0.0037 (17)
O2	0.102 (3)	0.044 (2)	0.052 (2)	0.024 (2)	0.001 (2)	0.0121 (17)
O3	0.098 (3)	0.053 (2)	0.054 (2)	0.026 (2)	0.022 (2)	0.0023 (18)
O4	0.095 (3)	0.027 (2)	0.074 (3)	−0.0002 (19)	−0.009 (2)	0.0005 (18)
O5	0.173 (5)	0.059 (3)	0.055 (3)	−0.057 (3)	−0.006 (3)	0.016 (2)
O6	0.101 (3)	0.046 (2)	0.050 (2)	−0.026 (2)	−0.022 (2)	0.0049 (17)
O7	0.063 (2)	0.0315 (18)	0.056 (2)	0.0090 (16)	0.0096 (17)	0.0037 (15)
O8	0.058 (2)	0.0317 (18)	0.054 (2)	−0.0078 (16)	−0.0026 (16)	0.0035 (15)
C1	0.040 (3)	0.031 (3)	0.055 (3)	0.004 (2)	0.001 (3)	0.002 (2)
C2	0.036 (3)	0.027 (3)	0.043 (3)	−0.001 (2)	−0.004 (2)	0.003 (2)
C3	0.043 (3)	0.026 (2)	0.038 (3)	0.000 (2)	−0.004 (2)	−0.001 (2)
C4	0.058 (3)	0.029 (3)	0.057 (3)	0.005 (2)	0.011 (3)	−0.003 (2)
C5	0.067 (4)	0.050 (4)	0.060 (4)	0.011 (3)	0.026 (3)	0.002 (3)
C6	0.072 (4)	0.035 (3)	0.054 (3)	0.005 (3)	0.020 (3)	0.011 (2)
C7	0.051 (3)	0.027 (3)	0.038 (3)	−0.003 (2)	−0.003 (2)	0.003 (2)
C8	0.070 (4)	0.039 (3)	0.043 (3)	0.014 (3)	0.007 (3)	0.001 (2)
C9	0.072 (4)	0.048 (3)	0.051 (3)	0.008 (3)	0.010 (3)	0.008 (3)
C10	0.077 (4)	0.077 (4)	0.073 (4)	−0.009 (3)	0.013 (3)	0.014 (3)
C11	0.086 (4)	0.066 (4)	0.056 (4)	0.019 (4)	−0.008 (3)	0.002 (3)
C12	0.073 (4)	0.085 (5)	0.069 (4)	−0.009 (4)	−0.018 (3)	−0.004 (3)
C13	0.144 (7)	0.109 (6)	0.088 (5)	0.025 (5)	−0.019 (5)	0.038 (4)
C14	0.053 (3)	0.032 (3)	0.056 (3)	−0.008 (2)	−0.004 (3)	0.004 (3)
C15	0.041 (3)	0.029 (3)	0.041 (3)	−0.005 (2)	0.001 (2)	0.002 (2)
C16	0.044 (3)	0.027 (3)	0.040 (3)	−0.004 (2)	0.002 (2)	−0.001 (2)
C17	0.056 (3)	0.035 (3)	0.056 (3)	−0.008 (2)	−0.001 (3)	−0.006 (2)
C18	0.063 (4)	0.040 (3)	0.048 (3)	−0.006 (3)	−0.018 (3)	0.003 (2)
C19	0.066 (4)	0.040 (3)	0.047 (3)	−0.014 (3)	−0.014 (3)	0.013 (2)
C20	0.056 (3)	0.034 (3)	0.036 (3)	−0.010 (3)	0.000 (2)	0.005 (2)
C21	0.073 (4)	0.040 (3)	0.041 (3)	−0.012 (3)	−0.006 (3)	0.003 (2)
C22	0.094 (4)	0.061 (4)	0.043 (3)	−0.014 (3)	−0.007 (3)	0.004 (3)
C23	0.107 (5)	0.069 (4)	0.067 (4)	0.003 (3)	−0.018 (4)	0.017 (3)
C24	0.120 (6)	0.096 (5)	0.067 (5)	−0.032 (5)	−0.001 (4)	0.002 (4)
C25	0.175 (8)	0.113 (6)	0.051 (4)	−0.036 (5)	−0.016 (4)	−0.008 (4)
C26	0.092 (6)	0.155 (8)	0.086 (5)	0.017 (5)	0.008 (4)	−0.011 (5)

Co1—N1	2.156 (4)	C8—C9	1.539 (6)
Co1—N3	2.016 (3)	C9—C11	1.468 (7)
Co1—N4	2.144 (3)	C9—C10	1.551 (7)
Co1—N6	2.019 (3)	C10—H10A	0.9600
Co1—O7	2.090 (3)	C10—H10B	0.9600
Co1—O8	2.085 (3)	C10—H10C	0.9600
N1—C6	1.321 (5)	C11—C13	1.531 (7)
N1—C2	1.361 (5)	C11—C12	1.548 (7)
N2—C7	1.303 (5)	C11—H11	0.9800
N2—C9	1.482 (6)	C12—H12A	0.9600
N2—H2	0.8600	C12—H12B	0.9600
N3—C7	1.351 (5)	C12—H12C	0.9600
N3—C8	1.371 (5)	C13—H13A	0.9600
N4—C19	1.325 (5)	C13—H13B	0.9600
N4—C15	1.364 (5)	C13—H13C	0.9600
N5—C20	1.292 (5)	C14—C16	1.539 (6)
N5—C22	1.474 (6)	C15—C16	1.396 (5)
N5—H5	0.8600	C15—C20	1.478 (6)
N6—C20	1.351 (5)	C16—C17	1.412 (6)
N6—C21	1.367 (5)	C17—C18	1.357 (6)
O1—C1	1.233 (5)	C17—H17	0.9300
O2—C1	1.249 (5)	C18—C19	1.377 (6)
O3—C8	1.232 (5)	C18—H18	0.9300
O4—C14	1.223 (5)	C19—H19	0.9300
O5—C14	1.233 (5)	C21—C22	1.549 (7)
O6—C21	1.230 (5)	C22—C24	1.442 (7)
O7—H7A	0.8500	C22—C23	1.585 (7)
O7—H7B	0.8500	C23—H23A	0.9600
O8—H8A	0.8500	C23—H23B	0.9600
O8—H8B	0.8500	C23—H23C	0.9600
C1—C3	1.531 (6)	C24—C26	1.500 (8)
C2—C3	1.390 (5)	C24—C25	1.542 (8)
C2—C7	1.487 (6)	C24—H24	0.9800
C3—C4	1.405 (6)	C25—H25A	0.9600
C4—C5	1.363 (6)	C25—H25B	0.9600
C4—H4	0.9300	C25—H25C	0.9600
C5—C6	1.369 (6)	C26—H26A	0.9600
C5—H5A	0.9300	C26—H26B	0.9600
C6—H6	0.9300	C26—H26C	0.9600
N3—Co1—N6	174.47 (15)	H10B—C10—H10C	109.5
N3—Co1—O8	94.68 (13)	C9—C11—C13	114.0 (5)
N6—Co1—O8	89.42 (13)	C9—C11—C12	110.6 (4)
N3—Co1—O7	89.18 (13)	C13—C11—C12	111.3 (5)
N6—Co1—O7	94.63 (13)	C9—C11—H11	106.8
O8—Co1—O7	88.65 (12)	C13—C11—H11	106.8
N3—Co1—N4	98.91 (14)	C12—C11—H11	106.8
N6—Co1—N4	77.27 (14)	C11—C12—H12A	109.5
O8—Co1—N4	165.91 (12)	C11—C12—H12B	109.5
O7—Co1—N4	87.84 (13)	H12A—C12—H12B	109.5
N3—Co1—N1	77.18 (14)	C11—C12—H12C	109.5
N6—Co1—N1	99.35 (14)	H12A—C12—H12C	109.5
O8—Co1—N1	87.48 (13)	H12B—C12—H12C	109.5
O7—Co1—N1	165.45 (13)	C11—C13—H13A	109.5
N4—Co1—N1	99.12 (14)	C11—C13—H13B	109.5
C6—N1—C2	118.4 (4)	H13A—C13—H13B	109.5
C6—N1—Co1	125.4 (3)	C11—C13—H13C	109.5
C2—N1—Co1	115.3 (3)	H13A—C13—H13C	109.5
C7—N2—C9	109.6 (4)	H13B—C13—H13C	109.5
C7—N2—H2	125.2	O4—C14—O5	124.9 (5)
C9—N2—H2	125.2	O4—C14—C16	114.6 (4)
C7—N3—C8	106.4 (4)	O5—C14—C16	120.4 (4)
C7—N3—Co1	116.2 (3)	N4—C15—C16	122.0 (4)
C8—N3—Co1	137.3 (3)	N4—C15—C20	111.0 (4)
C19—N4—C15	118.8 (4)	C16—C15—C20	127.1 (4)
C19—N4—Co1	125.2 (3)	C15—C16—C17	116.8 (4)
C15—N4—Co1	115.0 (3)	C15—C16—C14	127.7 (4)
C20—N5—C22	110.3 (4)	C17—C16—C14	115.6 (4)
C20—N5—H5	124.8	C18—C17—C16	120.4 (4)
C22—N5—H5	124.8	C18—C17—H17	119.8
C20—N6—C21	106.8 (4)	C16—C17—H17	119.8
C20—N6—Co1	116.3 (3)	C17—C18—C19	119.2 (5)
C21—N6—Co1	136.5 (3)	C17—C18—H18	120.4
Co1—O7—H7A	107.4	C19—C18—H18	120.4
Co1—O7—H7B	120.3	N4—C19—C18	122.7 (4)
H7A—O7—H7B	107.9	N4—C19—H19	118.6
Co1—O8—H8A	108.1	C18—C19—H19	118.6
Co1—O8—H8B	118.0	N5—C20—N6	114.8 (4)
H8A—O8—H8B	108.6	N5—C20—C15	127.3 (4)
O1—C1—O2	125.3 (4)	N6—C20—C15	117.9 (4)
O1—C1—C3	114.4 (4)	O6—C21—N6	125.0 (4)
O2—C1—C3	120.3 (4)	O6—C21—C22	125.8 (4)
N1—C2—C3	122.8 (4)	N6—C21—C22	109.0 (4)
N1—C2—C7	110.0 (4)	C24—C22—N5	111.6 (5)
C3—C2—C7	127.2 (4)	C24—C22—C21	117.1 (5)
C2—C3—C4	115.6 (4)	N5—C22—C21	98.7 (4)
C2—C3—C1	128.4 (4)	C24—C22—C23	109.0 (5)
C4—C3—C1	116.0 (4)	N5—C22—C23	110.1 (5)
C5—C4—C3	121.5 (4)	C21—C22—C23	110.0 (5)
C5—C4—H4	119.2	C22—C23—H23A	109.5
C3—C4—H4	119.2	C22—C23—H23B	109.5
C4—C5—C6	118.2 (5)	H23A—C23—H23B	109.5
C4—C5—H5A	120.9	C22—C23—H23C	109.5
C6—C5—H5A	120.9	H23A—C23—H23C	109.5
N1—C6—C5	123.2 (5)	H23B—C23—H23C	109.5
N1—C6—H6	118.4	C22—C24—C26	107.9 (6)
C5—C6—H6	118.4	C22—C24—C25	114.5 (6)
N2—C7—N3	115.3 (4)	C26—C24—C25	109.7 (6)
N2—C7—C2	126.1 (4)	C22—C24—H24	108.2
N3—C7—C2	118.6 (4)	C26—C24—H24	108.2
O3—C8—N3	125.5 (4)	C25—C24—H24	108.2
O3—C8—C9	124.7 (4)	C24—C25—H25A	109.5
N3—C8—C9	109.7 (4)	C24—C25—H25B	109.5
C11—C9—N2	112.4 (5)	H25A—C25—H25B	109.5
C11—C9—C8	112.4 (5)	C24—C25—H25C	109.5
N2—C9—C8	99.0 (4)	H25A—C25—H25C	109.5
C11—C9—C10	112.2 (4)	H25B—C25—H25C	109.5
N2—C9—C10	110.6 (4)	C24—C26—H26A	109.5
C8—C9—C10	109.5 (4)	C24—C26—H26B	109.5
C9—C10—H10A	109.5	H26A—C26—H26B	109.5
C9—C10—H10B	109.5	C24—C26—H26C	109.5
H10A—C10—H10B	109.5	H26A—C26—H26C	109.5
C9—C10—H10C	109.5	H26B—C26—H26C	109.5
H10A—C10—H10C	109.5
N3—Co1—N1—C6	175.4 (4)	Co1—N3—C8—O3	5.1 (9)
N6—Co1—N1—C6	−0.2 (4)	C7—N3—C8—C9	1.6 (5)
O8—Co1—N1—C6	−89.2 (4)	Co1—N3—C8—C9	−173.7 (4)
O7—Co1—N1—C6	−164.0 (4)	C7—N2—C9—C11	120.5 (5)
N4—Co1—N1—C6	78.3 (4)	C7—N2—C9—C8	1.6 (5)
N3—Co1—N1—C2	−15.5 (3)	C7—N2—C9—C10	−113.3 (5)
N6—Co1—N1—C2	168.9 (3)	O3—C8—C9—C11	60.4 (7)
O8—Co1—N1—C2	79.9 (3)	N3—C8—C9—C11	−120.8 (5)
O7—Co1—N1—C2	5.2 (7)	O3—C8—C9—N2	179.3 (5)
N4—Co1—N1—C2	−112.6 (3)	N3—C8—C9—N2	−2.0 (5)
O8—Co1—N3—C7	−74.9 (3)	O3—C8—C9—C10	−65.0 (7)
O7—Co1—N3—C7	−163.5 (3)	N3—C8—C9—C10	113.8 (5)
N4—Co1—N3—C7	108.8 (3)	N2—C9—C11—C13	71.2 (6)
N1—Co1—N3—C7	11.4 (3)	C8—C9—C11—C13	−178.1 (5)
O8—Co1—N3—C8	100.0 (5)	C10—C9—C11—C13	−54.2 (7)
O7—Co1—N3—C8	11.5 (5)	N2—C9—C11—C12	−55.1 (6)
N4—Co1—N3—C8	−76.2 (5)	C8—C9—C11—C12	55.6 (6)
N1—Co1—N3—C8	−173.6 (5)	C10—C9—C11—C12	179.5 (5)
N3—Co1—N4—C19	1.0 (4)	C19—N4—C15—C16	3.6 (7)
N6—Co1—N4—C19	176.9 (4)	Co1—N4—C15—C16	−165.4 (3)
O8—Co1—N4—C19	−163.5 (4)	C19—N4—C15—C20	−176.6 (4)
O7—Co1—N4—C19	−87.9 (4)	Co1—N4—C15—C20	14.5 (5)
N1—Co1—N4—C19	79.3 (4)	N4—C15—C16—C17	−2.9 (6)
N3—Co1—N4—C15	169.1 (3)	C20—C15—C16—C17	177.3 (4)
N6—Co1—N4—C15	−14.9 (3)	N4—C15—C16—C14	176.7 (4)
O8—Co1—N4—C15	4.6 (7)	C20—C15—C16—C14	−3.1 (8)
O7—Co1—N4—C15	80.3 (3)	O4—C14—C16—C15	−154.5 (5)
N1—Co1—N4—C15	−112.5 (3)	O5—C14—C16—C15	27.8 (8)
O8—Co1—N6—C20	−163.2 (3)	O4—C14—C16—C17	25.1 (6)
O7—Co1—N6—C20	−74.6 (3)	O5—C14—C16—C17	−152.6 (5)
N4—Co1—N6—C20	12.1 (3)	C15—C16—C17—C18	−0.2 (7)
N1—Co1—N6—C20	109.4 (3)	C14—C16—C17—C18	−179.8 (4)
O8—Co1—N6—C21	8.0 (5)	C16—C17—C18—C19	2.4 (8)
O7—Co1—N6—C21	96.6 (5)	C15—N4—C19—C18	−1.2 (7)
N4—Co1—N6—C21	−176.7 (5)	Co1—N4—C19—C18	166.5 (4)
N1—Co1—N6—C21	−79.4 (5)	C17—C18—C19—N4	−1.7 (8)
C6—N1—C2—C3	4.9 (7)	C22—N5—C20—N6	−2.1 (6)
Co1—N1—C2—C3	−165.0 (3)	C22—N5—C20—C15	178.0 (5)
C6—N1—C2—C7	−174.3 (4)	C21—N6—C20—N5	−2.0 (6)
Co1—N1—C2—C7	15.7 (4)	Co1—N6—C20—N5	171.7 (3)
N1—C2—C3—C4	−4.5 (6)	C21—N6—C20—C15	178.0 (4)
C7—C2—C3—C4	174.6 (4)	Co1—N6—C20—C15	−8.4 (5)
N1—C2—C3—C1	175.0 (4)	N4—C15—C20—N5	175.4 (5)
C7—C2—C3—C1	−5.9 (8)	C16—C15—C20—N5	−4.7 (8)
O1—C1—C3—C2	−153.4 (5)	N4—C15—C20—N6	−4.5 (6)
O2—C1—C3—C2	28.0 (7)	C16—C15—C20—N6	175.3 (4)
O1—C1—C3—C4	26.1 (6)	C20—N6—C21—O6	−178.4 (5)
O2—C1—C3—C4	−152.4 (4)	Co1—N6—C21—O6	9.8 (9)
C2—C3—C4—C5	0.6 (7)	C20—N6—C21—C22	5.0 (6)
C1—C3—C4—C5	−179.0 (5)	Co1—N6—C21—C22	−166.8 (4)
C3—C4—C5—C6	2.8 (8)	C20—N5—C22—C24	128.4 (6)
C2—N1—C6—C5	−1.2 (7)	C20—N5—C22—C21	4.6 (6)
Co1—N1—C6—C5	167.6 (4)	C20—N5—C22—C23	−110.5 (5)
C4—C5—C6—N1	−2.5 (8)	O6—C21—C22—C24	58.0 (8)
C9—N2—C7—N3	−0.8 (6)	N6—C21—C22—C24	−125.5 (5)
C9—N2—C7—C2	−177.9 (4)	O6—C21—C22—N5	177.7 (5)
C8—N3—C7—N2	−0.6 (6)	N6—C21—C22—N5	−5.8 (6)
Co1—N3—C7—N2	175.9 (3)	O6—C21—C22—C23	−67.2 (7)
C8—N3—C7—C2	176.8 (4)	N6—C21—C22—C23	109.4 (5)
Co1—N3—C7—C2	−6.7 (5)	N5—C22—C24—C26	−58.3 (7)
N1—C2—C7—N2	170.6 (4)	C21—C22—C24—C26	54.3 (7)
C3—C2—C7—N2	−8.6 (8)	C23—C22—C24—C26	179.9 (5)
N1—C2—C7—N3	−6.4 (6)	N5—C22—C24—C25	179.2 (5)
C3—C2—C7—N3	174.3 (4)	C21—C22—C24—C25	−68.2 (8)
C7—N3—C8—O3	−179.6 (5)	C23—C22—C24—C25	57.4 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.86	1.75	2.525 (5)	149
N5—H5···O5	0.86	1.77	2.537 (5)	148
O7—H7A···O3	0.85	2.11	2.888 (4)	151
O7—H7B···O1i	0.85	1.81	2.651 (4)	169
O8—H8A···O6	0.85	2.11	2.857 (4)	147
O8—H8B···O4ii	0.85	1.80	2.645 (4)	170

Table 1

Selected bond lengths (Å)

Co1—N1	2.156 (4)
Co1—N3	2.016 (3)
Co1—N4	2.144 (3)
Co1—N6	2.019 (3)
Co1—O7	2.090 (3)
Co1—O8	2.085 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.86	1.75	2.525 (5)	149
N5—H5⋯O5	0.86	1.77	2.537 (5)	148
O7—H7A⋯O3	0.85	2.11	2.888 (4)	151
O7—H7B⋯O1i	0.85	1.81	2.651 (4)	169
O8—H8A⋯O6	0.85	2.11	2.857 (4)	147
O8—H8B⋯O4ii	0.85	1.80	2.645 (4)	170

Symmetry codes: (i) ; (ii) .