catena-Poly[[aqua-(2,2'-bipyridyl)cobalt(II)]-μ-5-nitro-isophthalato].

In the crystal structure of the title compound, [Co(C(8)H(3)NO(6))(C(10)H(8)N(2))(H(2)O)](n), there are two symmetry-independent one-dimensional coordination polymers, which are approximately related by noncrystallographic inversion symmetry. Each zigzag chain is constructed from one Co(II) ion, one O-monodentate 5-nitro-isophthalate (ndc) dianion, one N,N'-bidentate 2,2'-bipyridyl ligand and one water mol-ecule. A symmetry-generated O,O'-bidentate ndc dianion completes the cobalt coordination environment, which could be described as very distorted cis-CoN(2)O(4) octa-hedral. The bridging ndc ligands result in parallel chains running along the a direction, and O-H⋯O hydrogen bonds arising from the water mol-ecules complete the structure.

Related literature

For uses of carboxylic acids in materials science, see: Church & Halvorson (1959 ▶); and in biological systems, see: Okabe & Oya (2000 ▶).

Experimental

Crystal data

[Co(C8H3NO6)(C10H8N2)(H2O)]

M = 442.24

Monoclinic,

a = 10.0125 (10) Å

b = 23.575 (2) Å

c = 15.403 (2) Å

β = 97.28 (1)°

V = 3606.3 (7) Å3

Z = 8

Mo Kα radiation

μ = 1.00 mm−1

T = 293 (2) K

0.43 × 0.28 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.673, T max = 0.825

18893 measured reflections

6672 independent reflections

5103 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.106

S = 1.01

6672 reflections

535 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.95 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038178/hb2844sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038178/hb2844Isup2.hkl

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

[Co(C8H3NO6)(C10H8N2)(H2O)]	F000 = 1800
Mr = 442.24	Dx = 1.629 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6672 reflections
a = 10.0125 (10) Å	θ = 1.7–25.5º
b = 23.575 (2) Å	µ = 1.00 mm−1
c = 15.403 (2) Å	T = 293 (2) K
β = 97.28 (1)º	Block, red
V = 3606.3 (7) Å3	0.43 × 0.28 × 0.20 mm
Z = 8

Bruker APEXII CCD diffractometer	6672 independent reflections
Radiation source: fine-focus sealed tube	5103 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.025
T = 293(2) K	θmax = 25.5º
ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −12→10
Tmin = 0.673, Tmax = 0.825	k = −28→22
18893 measured reflections	l = −18→18

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0548P)2 + 2.8058P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.032
6672 reflections	Δρmax = 0.95 e Å−3
535 parameters	Δρmin = −0.29 e Å−3
6 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
Co1	1.16169 (4)	0.154445 (14)	0.85573 (2)	0.02466 (11)
Co2	0.12374 (4)	0.354444 (15)	0.93350 (3)	0.02797 (12)
C1	0.0858 (3)	0.43912 (15)	0.7845 (2)	0.0469 (8)
H1	0.0715	0.4073	0.7489	0.056*
C2	0.0708 (4)	0.49272 (17)	0.7466 (3)	0.0555 (10)
H2	0.0482	0.4963	0.6864	0.067*
C3	0.0893 (4)	0.54031 (16)	0.7979 (3)	0.0570 (10)
H3	0.0810	0.5763	0.7731	0.068*
C4	0.1204 (3)	0.53368 (14)	0.8864 (3)	0.0474 (9)
H4	0.1307	0.5651	0.9231	0.057*
C5	0.1365 (3)	0.47893 (12)	0.9205 (2)	0.0363 (7)
C6	0.1704 (3)	0.46688 (12)	1.0143 (2)	0.0361 (7)
C7	0.1997 (3)	0.50925 (14)	1.0774 (3)	0.0490 (9)
H7	0.1978	0.5474	1.0616	0.059*
C8	0.2313 (3)	0.49307 (17)	1.1631 (3)	0.0557 (10)
H8	0.2506	0.5203	1.2067	0.067*
C9	0.2341 (4)	0.43613 (17)	1.1843 (3)	0.0559 (10)
H9	0.2569	0.4248	1.2421	0.067*
C10	0.2034 (3)	0.39623 (15)	1.1200 (2)	0.0468 (8)
H10	0.2049	0.3580	1.1351	0.056*
C11	0.5280 (3)	0.24937 (12)	1.02748 (19)	0.0320 (6)
H11	0.4449	0.2352	1.0380	0.038*
C12	0.6449 (3)	0.22104 (12)	1.05893 (19)	0.0321 (6)
C13	0.7703 (3)	0.24074 (12)	1.04616 (19)	0.0327 (7)
H13	0.8479	0.2213	1.0685	0.039*
C14	0.7776 (3)	0.29080 (11)	0.99863 (18)	0.0271 (6)
C15	0.9110 (3)	0.31378 (12)	0.9803 (2)	0.0312 (6)
C16	0.6606 (3)	0.31947 (12)	0.96577 (18)	0.0286 (6)
H16	0.6666	0.3527	0.9339	0.034*
C17	0.5354 (3)	0.29914 (12)	0.98002 (18)	0.0288 (6)
C18	0.4121 (3)	0.33266 (13)	0.9446 (2)	0.0325 (7)
C19	1.1953 (4)	0.07221 (15)	1.0079 (2)	0.0512 (9)
H19	1.2137	0.1044	1.0424	0.061*
C20	1.2036 (5)	0.01944 (18)	1.0474 (3)	0.0684 (12)
H20	1.2268	0.0164	1.1076	0.082*
C21	1.1774 (5)	−0.02879 (17)	0.9971 (3)	0.0688 (12)
H21	1.1813	−0.0645	1.0230	0.083*
C22	1.1455 (4)	−0.02303 (14)	0.9087 (2)	0.0526 (9)
H22	1.1289	−0.0547	0.8731	0.063*
C23	1.1386 (3)	0.03108 (12)	0.8732 (2)	0.0327 (7)
C24	1.1073 (3)	0.04138 (12)	0.7783 (2)	0.0314 (6)
C25	1.0794 (3)	−0.00192 (13)	0.7180 (2)	0.0411 (8)
H25	1.0787	−0.0396	0.7357	0.049*
C26	1.0526 (3)	0.01263 (15)	0.6307 (2)	0.0456 (8)
H26	1.0329	−0.0152	0.5883	0.055*
C27	1.0556 (3)	0.06936 (15)	0.6071 (2)	0.0459 (8)
H27	1.0365	0.0798	0.5486	0.055*
C28	1.0866 (3)	0.11017 (13)	0.6701 (2)	0.0381 (7)
H28	1.0889	0.1480	0.6532	0.046*
C29	0.8750 (3)	0.17566 (13)	0.8380 (2)	0.0336 (7)
C30	0.7500 (3)	0.20949 (12)	0.80607 (18)	0.0274 (6)
C31	0.7569 (3)	0.26263 (12)	0.76643 (19)	0.0314 (6)
H31	0.8396	0.2780	0.7575	0.038*
C32	0.6258 (3)	0.18764 (12)	0.81981 (19)	0.0297 (6)
H32	0.6210	0.1529	0.8477	0.036*
C33	0.6392 (3)	0.29172 (12)	0.7409 (2)	0.0347 (7)
C34	0.5084 (3)	0.21757 (12)	0.79203 (18)	0.0273 (6)
C35	0.5143 (3)	0.27061 (13)	0.75206 (19)	0.0332 (7)
H35	0.4363	0.2910	0.7336	0.040*
C36	0.3756 (3)	0.19401 (13)	0.8104 (2)	0.0331 (7)
H1W	1.243 (3)	0.2304 (11)	0.958 (3)	0.080*
H2W	1.126 (2)	0.2153 (14)	0.989 (3)	0.080*
H3W	0.164 (2)	0.2956 (15)	0.803 (3)	0.080*
H4W	0.042 (3)	0.2778 (10)	0.823 (3)	0.080*
N1	1.1134 (2)	0.09709 (10)	0.75443 (15)	0.0302 (5)
N2	1.1617 (3)	0.07823 (10)	0.92182 (16)	0.0349 (6)
N3	0.1199 (2)	0.43207 (10)	0.87001 (17)	0.0349 (6)
N4	0.1713 (2)	0.41090 (10)	1.03641 (17)	0.0361 (6)
N5	0.6352 (3)	0.16753 (12)	1.10790 (19)	0.0477 (7)
N6	0.6479 (3)	0.34937 (13)	0.7036 (2)	0.0578 (9)
O1	0.8634 (2)	0.12806 (12)	0.8691 (2)	0.0705 (9)
O2	0.98644 (19)	0.19824 (8)	0.82627 (15)	0.0379 (5)
O3	0.7556 (3)	0.37273 (12)	0.7088 (2)	0.0801 (10)
O4	0.5459 (3)	0.37066 (17)	0.6681 (3)	0.1342 (19)
O5	0.3733 (2)	0.14822 (9)	0.85254 (16)	0.0440 (6)
O6	0.26919 (19)	0.22039 (9)	0.78407 (15)	0.0422 (5)
O7	0.5264 (3)	0.14506 (14)	1.1063 (2)	0.0932 (12)
O8	0.7366 (3)	0.14819 (11)	1.14856 (19)	0.0642 (8)
O9	1.0167 (2)	0.28717 (9)	1.00726 (15)	0.0411 (5)
O10	0.9137 (2)	0.35927 (9)	0.93795 (16)	0.0442 (6)
O11	0.4241 (2)	0.37689 (11)	0.90426 (18)	0.0586 (7)
O12	0.30031 (19)	0.31194 (9)	0.96161 (15)	0.0409 (5)
O1W	1.1948 (2)	0.20370 (8)	0.97017 (15)	0.0371 (5)
O2W	0.0917 (2)	0.30554 (8)	0.81966 (16)	0.0374 (5)

	U11	U22	U33	U12	U13	U23
Co1	0.01864 (19)	0.02268 (19)	0.0325 (2)	0.00142 (14)	0.00270 (15)	0.00151 (15)
Co2	0.01822 (19)	0.0237 (2)	0.0425 (2)	0.00121 (14)	0.00602 (16)	0.00113 (16)
C1	0.0428 (19)	0.048 (2)	0.052 (2)	0.0030 (15)	0.0148 (16)	0.0066 (16)
C2	0.046 (2)	0.065 (3)	0.057 (2)	0.0082 (18)	0.0139 (18)	0.024 (2)
C3	0.043 (2)	0.042 (2)	0.090 (3)	0.0027 (16)	0.020 (2)	0.026 (2)
C4	0.0326 (18)	0.0322 (17)	0.080 (3)	0.0017 (14)	0.0173 (17)	0.0057 (17)
C5	0.0193 (14)	0.0299 (15)	0.062 (2)	−0.0004 (12)	0.0141 (14)	0.0001 (14)
C6	0.0188 (14)	0.0342 (16)	0.057 (2)	−0.0007 (12)	0.0101 (13)	−0.0045 (14)
C7	0.0352 (18)	0.0352 (18)	0.078 (3)	−0.0024 (14)	0.0127 (18)	−0.0098 (17)
C8	0.038 (2)	0.067 (3)	0.062 (3)	−0.0018 (17)	0.0042 (18)	−0.022 (2)
C9	0.043 (2)	0.073 (3)	0.052 (2)	0.0057 (18)	0.0078 (17)	−0.0072 (19)
C10	0.0398 (19)	0.051 (2)	0.050 (2)	0.0067 (16)	0.0065 (16)	0.0001 (17)
C11	0.0204 (14)	0.0411 (16)	0.0348 (17)	−0.0058 (12)	0.0051 (12)	0.0010 (13)
C12	0.0267 (15)	0.0373 (16)	0.0323 (16)	−0.0020 (12)	0.0039 (12)	0.0048 (12)
C13	0.0210 (14)	0.0419 (17)	0.0347 (17)	0.0023 (12)	0.0012 (12)	0.0005 (13)
C14	0.0194 (14)	0.0317 (14)	0.0313 (15)	−0.0005 (11)	0.0069 (11)	−0.0043 (12)
C15	0.0185 (14)	0.0359 (16)	0.0403 (17)	0.0013 (12)	0.0077 (12)	−0.0087 (13)
C16	0.0228 (14)	0.0299 (14)	0.0336 (16)	−0.0011 (11)	0.0054 (12)	−0.0007 (12)
C17	0.0194 (14)	0.0358 (16)	0.0310 (16)	0.0001 (11)	0.0023 (11)	−0.0047 (12)
C18	0.0209 (15)	0.0387 (17)	0.0373 (17)	0.0023 (12)	0.0010 (12)	−0.0054 (13)
C19	0.070 (3)	0.048 (2)	0.0355 (19)	0.0013 (18)	0.0076 (17)	0.0048 (15)
C20	0.102 (4)	0.065 (3)	0.038 (2)	0.005 (2)	0.009 (2)	0.0146 (19)
C21	0.096 (3)	0.046 (2)	0.063 (3)	0.002 (2)	0.008 (2)	0.030 (2)
C22	0.068 (3)	0.0338 (18)	0.056 (2)	−0.0038 (17)	0.0053 (19)	0.0100 (16)
C23	0.0258 (15)	0.0308 (15)	0.0415 (18)	−0.0007 (12)	0.0043 (12)	0.0044 (13)
C24	0.0230 (14)	0.0304 (15)	0.0408 (17)	−0.0015 (12)	0.0042 (12)	0.0016 (13)
C25	0.0343 (17)	0.0329 (16)	0.056 (2)	−0.0028 (13)	0.0052 (15)	−0.0044 (15)
C26	0.0389 (19)	0.051 (2)	0.046 (2)	−0.0031 (15)	0.0035 (15)	−0.0147 (16)
C27	0.045 (2)	0.055 (2)	0.0367 (18)	0.0019 (16)	−0.0003 (15)	−0.0041 (15)
C28	0.0405 (18)	0.0378 (17)	0.0353 (17)	0.0061 (14)	0.0027 (14)	0.0054 (13)
C29	0.0221 (15)	0.0413 (17)	0.0369 (17)	0.0018 (13)	0.0017 (12)	0.0045 (13)
C30	0.0185 (14)	0.0351 (15)	0.0285 (15)	0.0014 (11)	0.0021 (11)	−0.0006 (12)
C31	0.0192 (14)	0.0402 (16)	0.0351 (16)	−0.0014 (12)	0.0045 (12)	0.0051 (13)
C32	0.0256 (15)	0.0311 (15)	0.0328 (15)	−0.0014 (12)	0.0060 (12)	−0.0004 (12)
C33	0.0303 (16)	0.0368 (16)	0.0379 (17)	0.0033 (13)	0.0078 (13)	0.0108 (13)
C34	0.0193 (13)	0.0346 (15)	0.0284 (15)	−0.0007 (11)	0.0047 (11)	−0.0063 (12)
C35	0.0215 (14)	0.0439 (17)	0.0340 (16)	0.0086 (12)	0.0030 (12)	0.0023 (13)
C36	0.0240 (15)	0.0401 (17)	0.0361 (17)	−0.0022 (13)	0.0070 (12)	−0.0110 (13)
N1	0.0251 (12)	0.0298 (12)	0.0358 (14)	0.0034 (10)	0.0039 (10)	0.0004 (10)
N2	0.0335 (14)	0.0349 (14)	0.0369 (15)	−0.0008 (11)	0.0067 (11)	0.0042 (11)
N3	0.0247 (13)	0.0352 (14)	0.0458 (17)	0.0018 (10)	0.0085 (11)	0.0055 (11)
N4	0.0264 (13)	0.0343 (14)	0.0483 (16)	0.0041 (10)	0.0079 (11)	−0.0007 (11)
N5	0.0348 (16)	0.0546 (17)	0.0532 (18)	−0.0040 (14)	0.0034 (13)	0.0203 (14)
N6	0.0458 (19)	0.0573 (19)	0.073 (2)	0.0145 (16)	0.0191 (16)	0.0331 (16)
O1	0.0359 (14)	0.0722 (18)	0.105 (2)	0.0136 (13)	0.0152 (14)	0.0578 (17)
O2	0.0161 (10)	0.0346 (11)	0.0623 (14)	0.0004 (8)	0.0022 (9)	−0.0024 (10)
O3	0.065 (2)	0.0644 (18)	0.108 (2)	−0.0176 (15)	−0.0012 (17)	0.0410 (17)
O4	0.0504 (19)	0.129 (3)	0.228 (5)	0.039 (2)	0.036 (2)	0.134 (3)
O5	0.0274 (12)	0.0441 (13)	0.0621 (15)	−0.0034 (9)	0.0117 (10)	0.0051 (11)
O6	0.0187 (10)	0.0491 (13)	0.0594 (15)	0.0039 (9)	0.0073 (10)	−0.0021 (11)
O7	0.0504 (18)	0.100 (2)	0.123 (3)	−0.0321 (16)	−0.0136 (18)	0.068 (2)
O8	0.0439 (15)	0.0619 (17)	0.087 (2)	0.0111 (12)	0.0070 (14)	0.0357 (14)
O9	0.0185 (10)	0.0453 (12)	0.0603 (14)	0.0035 (9)	0.0079 (10)	−0.0007 (10)
O10	0.0276 (11)	0.0363 (12)	0.0711 (16)	−0.0028 (9)	0.0161 (11)	0.0094 (11)
O11	0.0374 (14)	0.0576 (16)	0.0799 (18)	0.0077 (11)	0.0040 (13)	0.0303 (14)
O12	0.0190 (10)	0.0378 (12)	0.0658 (15)	0.0009 (9)	0.0052 (10)	−0.0032 (10)
O1W	0.0303 (12)	0.0335 (11)	0.0465 (13)	0.0030 (9)	0.0009 (10)	−0.0036 (9)
O2W	0.0287 (11)	0.0335 (11)	0.0502 (13)	0.0025 (9)	0.0050 (10)	0.0004 (10)

Co1—N2	2.065 (2)	C19—C20	1.382 (5)
Co1—N1	2.075 (2)	C19—H19	0.9300
Co1—O2	2.0369 (19)	C20—C21	1.382 (6)
Co1—O1W	2.102 (2)	C20—H20	0.9300
Co1—O5i	2.131 (2)	C21—C22	1.365 (5)
Co1—O6i	2.257 (2)	C21—H21	0.9300
Co2—N3	2.073 (2)	C22—C23	1.386 (4)
Co2—N4	2.078 (3)	C22—H22	0.9300
Co2—O12	2.031 (2)	C23—N2	1.344 (4)
Co2—O2W	2.089 (2)	C23—C24	1.475 (4)
Co2—O10ii	2.116 (2)	C24—N1	1.367 (4)
Co2—O9ii	2.294 (2)	C24—C25	1.385 (4)
C1—N3	1.329 (4)	C25—C26	1.380 (5)
C1—C2	1.392 (5)	C25—H25	0.9300
C1—H1	0.9300	C26—C27	1.387 (5)
C2—C3	1.372 (6)	C26—H26	0.9300
C2—H2	0.9300	C27—C28	1.374 (4)
C3—C4	1.367 (6)	C27—H27	0.9300
C3—H3	0.9300	C28—N1	1.329 (4)
C4—C5	1.395 (4)	C28—H28	0.9300
C4—H4	0.9300	C29—O1	1.231 (4)
C5—N3	1.349 (4)	C29—O2	1.270 (3)
C5—C6	1.470 (5)	C29—C30	1.513 (4)
C6—N4	1.362 (4)	C30—C32	1.386 (4)
C6—C7	1.398 (5)	C30—C31	1.399 (4)
C7—C8	1.373 (5)	C31—C33	1.377 (4)
C7—H7	0.9300	C31—H31	0.9300
C8—C9	1.381 (5)	C32—C34	1.391 (4)
C8—H8	0.9300	C32—H32	0.9300
C9—C10	1.372 (5)	C33—C35	1.377 (4)
C9—H9	0.9300	C33—N6	1.482 (4)
C10—N4	1.332 (4)	C34—C35	1.398 (4)
C10—H10	0.9300	C34—C36	1.500 (4)
C11—C12	1.381 (4)	C35—H35	0.9300
C11—C17	1.389 (4)	C36—O6	1.256 (3)
C11—H11	0.9300	C36—O5	1.261 (4)
C12—C13	1.376 (4)	C36—Co1ii	2.515 (3)
C12—N5	1.479 (4)	N5—O7	1.209 (4)
C13—C14	1.396 (4)	N5—O8	1.212 (3)
C13—H13	0.9300	N6—O3	1.204 (4)
C14—C16	1.390 (4)	N6—O4	1.205 (4)
C14—C15	1.501 (4)	O5—Co1ii	2.131 (2)
C15—O9	1.255 (3)	O6—Co1ii	2.257 (2)
C15—O10	1.257 (4)	O9—Co2i	2.294 (2)
C16—C17	1.386 (4)	O10—Co2i	2.116 (2)
C16—H16	0.9300	O1W—H1W	0.830 (10)
C17—C18	1.508 (4)	O1W—H2W	0.830 (10)
C18—O11	1.228 (4)	O2W—H3W	0.835 (10)
C18—O12	1.278 (3)	O2W—H4W	0.831 (10)
C19—N2	1.334 (4)
O2—Co1—N2	119.80 (9)	C20—C19—H19	119.1
O2—Co1—N1	92.92 (9)	C19—C20—C21	119.9 (4)
N2—Co1—N1	77.83 (9)	C19—C20—H20	120.1
O2—Co1—O1W	86.94 (8)	C21—C20—H20	120.1
N2—Co1—O1W	94.42 (9)	C22—C21—C20	118.7 (3)
N1—Co1—O1W	171.00 (9)	C22—C21—H21	120.6
O2—Co1—O5i	149.41 (9)	C20—C21—H21	120.6
N2—Co1—O5i	90.78 (9)	C21—C22—C23	118.6 (3)
N1—Co1—O5i	94.31 (9)	C21—C22—H22	120.7
O1W—Co1—O5i	90.33 (9)	C23—C22—H22	120.7
O2—Co1—O6i	89.58 (8)	N2—C23—C22	123.0 (3)
N2—Co1—O6i	150.47 (9)	N2—C23—C24	114.6 (2)
N1—Co1—O6i	99.27 (9)	C22—C23—C24	122.4 (3)
O1W—Co1—O6i	89.73 (8)	N1—C24—C25	122.7 (3)
O5i—Co1—O6i	59.93 (8)	N1—C24—C23	114.4 (2)
O12—Co2—N3	119.99 (9)	C25—C24—C23	122.9 (3)
O12—Co2—N4	92.54 (9)	C26—C25—C24	117.9 (3)
N3—Co2—N4	77.48 (10)	C26—C25—H25	121.0
O12—Co2—O2W	86.76 (9)	C24—C25—H25	121.0
N3—Co2—O2W	95.71 (9)	C25—C26—C27	119.2 (3)
N4—Co2—O2W	171.71 (10)	C25—C26—H26	120.4
O12—Co2—O10ii	149.51 (9)	C27—C26—H26	120.4
N3—Co2—O10ii	90.50 (9)	C28—C27—C26	120.0 (3)
N4—Co2—O10ii	94.22 (9)	C28—C27—H27	120.0
O2W—Co2—O10ii	90.54 (9)	C26—C27—H27	120.0
O12—Co2—O9ii	90.11 (8)	N1—C28—C27	121.8 (3)
N3—Co2—O9ii	149.55 (8)	N1—C28—H28	119.1
N4—Co2—O9ii	98.13 (9)	C27—C28—H28	119.1
O2W—Co2—O9ii	90.14 (8)	O1—C29—O2	124.4 (3)
O10ii—Co2—O9ii	59.50 (8)	O1—C29—C30	119.5 (3)
N3—C1—C2	122.0 (4)	O2—C29—C30	116.0 (3)
N3—C1—H1	119.0	C32—C30—C31	119.6 (2)
C2—C1—H1	119.0	C32—C30—C29	118.4 (3)
C3—C2—C1	120.1 (4)	C31—C30—C29	121.9 (2)
C3—C2—H2	120.0	C33—C31—C30	118.9 (3)
C1—C2—H2	120.0	C33—C31—H31	120.6
C4—C3—C2	118.6 (3)	C30—C31—H31	120.6
C4—C3—H3	120.7	C30—C32—C34	120.3 (3)
C2—C3—H3	120.7	C30—C32—H32	119.9
C3—C4—C5	118.8 (3)	C34—C32—H32	119.9
C3—C4—H4	120.6	C35—C33—C31	122.8 (3)
C5—C4—H4	120.6	C35—C33—N6	118.6 (3)
N3—C5—C4	122.7 (3)	C31—C33—N6	118.5 (3)
N3—C5—C6	113.9 (3)	C32—C34—C35	120.5 (3)
C4—C5—C6	123.4 (3)	C32—C34—C36	119.2 (3)
N4—C6—C7	121.6 (3)	C35—C34—C36	120.2 (2)
N4—C6—C5	115.2 (3)	C33—C35—C34	117.9 (3)
C7—C6—C5	123.2 (3)	C33—C35—H35	121.0
C8—C7—C6	118.2 (3)	C34—C35—H35	121.0
C8—C7—H7	120.9	O6—C36—O5	121.3 (3)
C6—C7—H7	120.9	O6—C36—C34	119.4 (3)
C7—C8—C9	119.5 (3)	O5—C36—C34	119.3 (3)
C7—C8—H8	120.2	O6—C36—Co1ii	63.61 (16)
C9—C8—H8	120.3	O5—C36—Co1ii	57.85 (15)
C10—C9—C8	120.0 (4)	C34—C36—Co1ii	174.8 (2)
C10—C9—H9	120.0	C28—N1—C24	118.4 (3)
C8—C9—H9	120.0	C28—N1—Co1	125.6 (2)
N4—C10—C9	121.6 (3)	C24—N1—Co1	115.95 (19)
N4—C10—H10	119.2	C19—N2—C23	118.0 (3)
C9—C10—H10	119.2	C19—N2—Co1	124.5 (2)
C12—C11—C17	119.6 (3)	C23—N2—Co1	117.12 (19)
C12—C11—H11	120.2	C1—N3—C5	117.8 (3)
C17—C11—H11	120.2	C1—N3—Co2	124.4 (2)
C13—C12—C11	122.3 (3)	C5—N3—Co2	117.2 (2)
C13—C12—N5	118.7 (3)	C10—N4—C6	119.1 (3)
C11—C12—N5	119.0 (3)	C10—N4—Co2	125.1 (2)
C12—C13—C14	118.0 (3)	C6—N4—Co2	115.9 (2)
C12—C13—H13	121.0	O7—N5—O8	122.6 (3)
C14—C13—H13	121.0	O7—N5—C12	118.7 (3)
C16—C14—C13	120.3 (3)	O8—N5—C12	118.7 (3)
C16—C14—C15	119.0 (3)	O3—N6—O4	122.7 (3)
C13—C14—C15	120.7 (2)	O3—N6—C33	119.3 (3)
O9—C15—O10	121.7 (3)	O4—N6—C33	118.0 (3)
O9—C15—C14	119.4 (3)	C29—O2—Co1	120.23 (19)
O10—C15—C14	118.9 (2)	C36—O5—Co1ii	92.08 (17)
C17—C16—C14	120.8 (3)	C36—O6—Co1ii	86.49 (18)
C17—C16—H16	119.6	C15—O9—Co2i	85.29 (18)
C14—C16—H16	119.6	C15—O10—Co2i	93.31 (17)
C16—C17—C11	119.0 (3)	C18—O12—Co2	121.93 (19)
C16—C17—C18	118.5 (3)	Co1—O1W—H1W	105 (3)
C11—C17—C18	122.5 (3)	Co1—O1W—H2W	115 (3)
O11—C18—O12	124.9 (3)	H1W—O1W—H2W	111.4 (18)
O11—C18—C17	120.0 (3)	Co2—O2W—H3W	111 (3)
O12—C18—C17	115.1 (3)	Co2—O2W—H4W	114 (3)
N2—C19—C20	121.7 (3)	H3W—O2W—H4W	111.0 (17)
N2—C19—H19	119.1

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O12i	0.830 (10)	2.01 (2)	2.771 (3)	153 (3)
O2W—H4W···O2ii	0.831 (10)	1.957 (17)	2.747 (3)	159 (3)
O1W—H2W···O9	0.830 (10)	2.05 (2)	2.763 (3)	143 (3)
O2W—H3W···O6	0.835 (10)	2.10 (3)	2.781 (3)	138 (3)

Table 1

Selected bond lengths (Å)

Co1—N2	2.065 (2)
Co1—N1	2.075 (2)
Co1—O2	2.0369 (19)
Co1—O1W	2.102 (2)
Co1—O5i	2.131 (2)
Co1—O6i	2.257 (2)
Co2—N3	2.073 (2)
Co2—N4	2.078 (3)
Co2—O12	2.031 (2)
Co2—O2W	2.089 (2)
Co2—O10ii	2.116 (2)
Co2—O9ii	2.294 (2)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O12i	0.830 (10)	2.01 (2)	2.771 (3)	153 (3)
O2W—H4W⋯O2ii	0.831 (10)	1.957 (17)	2.747 (3)	159 (3)
O1W—H2W⋯O9	0.830 (10)	2.05 (2)	2.763 (3)	143 (3)
O2W—H3W⋯O6	0.835 (10)	2.10 (3)	2.781 (3)	138 (3)

Symmetry codes: (i) ; (ii) .