Poly[[aqua-(μ(7)-biphenyl-3,3',4,4'-tetra-carboxyl-ato)(1,10-phenanthroline)dicobalt(II)] monohydrate].

In the title compound, {[Co(2)(C(16)H(6)O(8))(C(12)H(8)N(2))(H(2)O)(2)]·H(2)O}(n), one Co(II) ion has a {CoN(2)O(4)} distorted octa-hedral environment defined by two N atoms of one 1,10-phenanthroline (phen) ligand, three O atoms of the carboxyl-ate groups of three biphenyl-3,3',4,4'-tetra-carboxyl-ate (BPTC) ligands, one of which is bidentate, and one O atom from one coordinated water mol-ecule. The other Co(II) atom is surrounded by six O atoms from four different BPTC ligands and one coordinated water mol-ecule. Each BPTC ligand forms eight coordination bonds with seven Co(II) atoms, leading to a layer structure along the ac plane. Uncoordinated water mol-ecules occupy the space between the layers, and inter-act via inter-layer O-H⋯O hydrogen bonds along the b axis, generating a three-dimensional supra-molecular network.

Related literature

For applications of compounds with metal-organic framework structures (MOFs), see: Rowsell & Yaghi (2005 ▶). For related structures, see: Zhu et al. (2008 ▶); Konar et al. (2004 ▶).

Experimental

Crystal data

[Co2(C16H6O8)(C12H8N2)(H2O)2]·H2O

M = 678.32

Triclinic,

a = 9.793 (3) Å

b = 10.885 (3) Å

c = 12.453 (3) Å

α = 97.567 (4)°

β = 102.608 (4)°

γ = 95.653 (4)°

V = 1273.1 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.38 mm−1

T = 298 K

0.40 × 0.17 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.609, T max = 0.810

6716 measured reflections

4641 independent reflections

3194 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.113

S = 0.98

4641 reflections

388 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.50 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536811028224/bg2411sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028224/bg2411Isup2.hkl

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

[Co2(C16H6O8)(C12H8N2)(H2O)2]·H2O	Z = 2
Mr = 678.32	F(000) = 688
Triclinic, P1	Dx = 1.770 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.793 (3) Å	Cell parameters from 1160 reflections
b = 10.885 (3) Å	θ = 2.3–22.3°
c = 12.453 (3) Å	µ = 1.38 mm−1
α = 97.567 (4)°	T = 298 K
β = 102.608 (4)°	Block, red
γ = 95.653 (4)°	0.40 × 0.17 × 0.16 mm
V = 1273.1 (6) Å3

Bruker SMART CCD area-detector diffractometer	4641 independent reflections
Radiation source: fine-focus sealed tube	3194 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→9
Tmin = 0.609, Tmax = 0.810	k = −9→13
6716 measured reflections	l = −14→15

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0467P)2] where P = (Fo2 + 2Fc2)/3
4641 reflections	(Δ/σ)max = 0.001
388 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.50 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
C1	−0.1205 (5)	0.5902 (4)	0.6684 (4)	0.0227 (11)
C2	−0.0391 (5)	0.6133 (4)	0.7872 (3)	0.0209 (10)
C3	−0.0950 (5)	0.6775 (4)	0.8670 (4)	0.0284 (12)
H3	−0.1796	0.7094	0.8450	0.034*
C4	−0.0286 (5)	0.6957 (4)	0.9786 (4)	0.0298 (12)
H4	−0.0699	0.7388	1.0300	0.036*
C5	0.0979 (5)	0.6512 (4)	1.0160 (3)	0.0189 (10)
C6	0.1527 (5)	0.5852 (4)	0.9355 (3)	0.0234 (11)
H6	0.2372	0.5535	0.9583	0.028*
C7	0.0872 (5)	0.5642 (4)	0.8227 (3)	0.0191 (10)
C8	0.1543 (5)	0.4826 (5)	0.7467 (3)	0.0224 (11)
C9	0.1711 (4)	0.6716 (4)	1.1364 (3)	0.0194 (10)
C10	0.1249 (5)	0.7513 (4)	1.2133 (4)	0.0297 (12)
H10	0.0491	0.7939	1.1891	0.036*
C11	0.1904 (5)	0.7684 (5)	1.3263 (4)	0.0317 (12)
H11	0.1585	0.8230	1.3765	0.038*
C12	0.3014 (5)	0.7054 (4)	1.3644 (4)	0.0231 (11)
C13	0.3634 (5)	0.7284 (5)	1.4884 (4)	0.0248 (11)
C14	0.3493 (5)	0.6257 (4)	1.2883 (3)	0.0209 (10)
C15	0.4728 (5)	0.5573 (4)	1.3218 (4)	0.0230 (11)
C16	0.2826 (5)	0.6097 (4)	1.1761 (3)	0.0225 (10)
H16	0.3144	0.5550	1.1260	0.027*
C17	0.5542 (5)	0.7004 (5)	0.9733 (4)	0.0369 (13)
H17	0.6056	0.6388	0.9503	0.044*
C18	0.5861 (6)	0.7519 (5)	1.0863 (4)	0.0459 (15)
H18	0.6582	0.7257	1.1365	0.055*
C19	0.5106 (6)	0.8406 (5)	1.1219 (4)	0.0446 (15)
H19	0.5308	0.8756	1.1968	0.054*
C20	0.4023 (6)	0.8790 (5)	1.0452 (4)	0.0343 (13)
C21	0.3795 (5)	0.8238 (4)	0.9332 (4)	0.0272 (11)
C22	0.2701 (5)	0.8587 (4)	0.8500 (4)	0.0267 (11)
C23	0.1811 (6)	0.9417 (5)	0.8828 (4)	0.0380 (13)
C24	0.2065 (6)	0.9964 (5)	0.9968 (5)	0.0476 (15)
H24	0.1481	1.0524	1.0184	0.057*
C25	0.3128 (7)	0.9689 (5)	1.0736 (5)	0.0475 (15)
H25	0.3290	1.0088	1.1469	0.057*
C26	0.0685 (7)	0.9626 (5)	0.7995 (5)	0.0550 (17)
H26	0.0046	1.0151	0.8173	0.066*
C27	0.0522 (6)	0.9065 (6)	0.6930 (5)	0.0533 (17)
H27	−0.0217	0.9215	0.6373	0.064*
C28	0.1466 (6)	0.8265 (5)	0.6673 (4)	0.0381 (13)
H28	0.1328	0.7869	0.5941	0.046*
Co1	0.39769 (6)	0.67515 (6)	0.72127 (5)	0.02274 (18)
Co2	0.24578 (6)	0.44660 (6)	0.52994 (5)	0.02263 (18)
N1	0.2553 (4)	0.8043 (4)	0.7428 (3)	0.0277 (9)
N2	0.4548 (4)	0.7350 (4)	0.8980 (3)	0.0273 (9)
O1	−0.0796 (3)	0.5208 (3)	0.5955 (2)	0.0285 (8)
O2	−0.2316 (3)	0.6395 (3)	0.6414 (2)	0.0304 (8)
O3	0.1484 (4)	0.3712 (3)	0.7556 (3)	0.0385 (9)
O4	0.2165 (3)	0.5344 (3)	0.6805 (2)	0.0229 (7)
O5	0.4838 (3)	0.4631 (3)	1.2562 (2)	0.0284 (8)
O6	0.5598 (3)	0.6015 (3)	1.4135 (2)	0.0264 (8)
O7	0.4224 (4)	0.8357 (3)	1.5296 (2)	0.0352 (9)
O8	0.3428 (3)	0.6420 (3)	1.5449 (2)	0.0217 (7)
O9	0.1558 (4)	0.2681 (3)	0.5513 (2)	0.0376 (9)
H9A	0.1290	0.2480	0.6078	0.045*
H9B	0.1354	0.2042	0.5007	0.045*
O10	0.5871 (3)	0.7894 (3)	0.7169 (2)	0.0306 (8)
H10A	0.6525	0.7612	0.6901	0.037*
H10B	0.5721	0.8574	0.6925	0.037*
O11	0.3441 (5)	0.0884 (4)	0.5642 (4)	0.0968 (19)
H11A	0.3480	0.0115	0.5697	0.116*
H11B	0.4080	0.1111	0.5312	0.116*

	U11	U22	U33	U12	U13	U23
C1	0.015 (2)	0.028 (3)	0.023 (2)	−0.001 (2)	0.001 (2)	0.003 (2)
C2	0.019 (2)	0.027 (3)	0.014 (2)	0.003 (2)	−0.0016 (19)	0.003 (2)
C3	0.021 (3)	0.041 (3)	0.022 (3)	0.013 (2)	0.001 (2)	0.003 (2)
C4	0.033 (3)	0.038 (3)	0.018 (2)	0.011 (2)	0.006 (2)	−0.002 (2)
C5	0.021 (3)	0.021 (3)	0.015 (2)	0.004 (2)	0.0047 (19)	0.0034 (19)
C6	0.021 (3)	0.028 (3)	0.021 (2)	0.007 (2)	0.002 (2)	0.005 (2)
C7	0.023 (3)	0.025 (3)	0.011 (2)	0.004 (2)	0.0062 (18)	0.0035 (19)
C8	0.016 (2)	0.035 (3)	0.013 (2)	0.008 (2)	−0.0029 (19)	0.000 (2)
C9	0.019 (2)	0.024 (3)	0.015 (2)	0.004 (2)	0.0021 (19)	0.003 (2)
C10	0.034 (3)	0.032 (3)	0.023 (3)	0.017 (2)	0.001 (2)	0.005 (2)
C11	0.040 (3)	0.040 (3)	0.016 (2)	0.022 (3)	0.004 (2)	−0.001 (2)
C12	0.024 (3)	0.022 (3)	0.023 (2)	0.001 (2)	0.004 (2)	0.006 (2)
C13	0.025 (3)	0.034 (3)	0.016 (2)	0.016 (2)	0.001 (2)	0.001 (2)
C14	0.023 (3)	0.025 (3)	0.015 (2)	0.007 (2)	0.0029 (19)	0.005 (2)
C15	0.016 (2)	0.034 (3)	0.022 (2)	0.007 (2)	0.008 (2)	0.010 (2)
C16	0.024 (3)	0.024 (3)	0.019 (2)	0.006 (2)	0.002 (2)	0.002 (2)
C17	0.033 (3)	0.050 (4)	0.026 (3)	0.015 (3)	0.002 (2)	0.004 (3)
C18	0.045 (4)	0.062 (4)	0.024 (3)	0.004 (3)	−0.004 (3)	0.005 (3)
C19	0.055 (4)	0.049 (4)	0.022 (3)	−0.014 (3)	0.007 (3)	−0.003 (3)
C20	0.042 (3)	0.036 (3)	0.023 (3)	−0.006 (3)	0.012 (2)	−0.004 (2)
C21	0.032 (3)	0.027 (3)	0.021 (2)	−0.004 (2)	0.009 (2)	−0.002 (2)
C22	0.031 (3)	0.021 (3)	0.028 (3)	0.003 (2)	0.008 (2)	0.001 (2)
C23	0.052 (4)	0.028 (3)	0.039 (3)	0.012 (3)	0.017 (3)	0.004 (2)
C24	0.066 (4)	0.035 (3)	0.050 (4)	0.017 (3)	0.033 (3)	−0.006 (3)
C25	0.065 (4)	0.039 (4)	0.036 (3)	0.001 (3)	0.019 (3)	−0.012 (3)
C26	0.068 (5)	0.045 (4)	0.063 (4)	0.034 (3)	0.027 (4)	0.012 (3)
C27	0.056 (4)	0.064 (4)	0.047 (4)	0.035 (3)	0.011 (3)	0.017 (3)
C28	0.045 (4)	0.043 (4)	0.028 (3)	0.015 (3)	0.010 (3)	0.004 (3)
Co1	0.0226 (4)	0.0293 (4)	0.0144 (3)	0.0090 (3)	0.0007 (3)	−0.0016 (3)
Co2	0.0197 (4)	0.0316 (4)	0.0136 (3)	0.0072 (3)	−0.0016 (3)	−0.0011 (3)
N1	0.032 (2)	0.030 (2)	0.023 (2)	0.0107 (19)	0.0061 (18)	0.0034 (18)
N2	0.024 (2)	0.035 (3)	0.022 (2)	0.0073 (19)	0.0032 (18)	0.0003 (19)
O1	0.0256 (19)	0.041 (2)	0.0142 (16)	0.0109 (16)	−0.0018 (14)	−0.0061 (15)
O2	0.0232 (19)	0.050 (2)	0.0155 (16)	0.0147 (16)	−0.0021 (14)	0.0003 (15)
O3	0.057 (3)	0.033 (2)	0.032 (2)	0.0186 (19)	0.0175 (18)	0.0101 (17)
O4	0.0182 (17)	0.033 (2)	0.0159 (15)	0.0016 (14)	0.0036 (13)	−0.0008 (14)
O5	0.030 (2)	0.033 (2)	0.0183 (16)	0.0156 (16)	−0.0006 (14)	−0.0055 (15)
O6	0.0196 (18)	0.039 (2)	0.0164 (16)	0.0134 (15)	−0.0035 (14)	−0.0042 (15)
O7	0.047 (2)	0.024 (2)	0.0256 (18)	−0.0012 (17)	−0.0046 (16)	−0.0016 (16)
O8	0.0254 (18)	0.0271 (19)	0.0116 (15)	0.0054 (14)	0.0011 (13)	0.0031 (14)
O9	0.052 (2)	0.033 (2)	0.0264 (18)	−0.0014 (17)	0.0126 (17)	−0.0021 (16)
O10	0.031 (2)	0.030 (2)	0.0276 (18)	0.0052 (15)	0.0039 (15)	−0.0027 (15)
O11	0.104 (4)	0.038 (3)	0.184 (5)	0.023 (3)	0.094 (4)	0.031 (3)

C1—O2	1.260 (5)	C19—H19	0.9300
C1—O1	1.262 (5)	C20—C21	1.404 (6)
C1—C2	1.495 (6)	C20—C25	1.437 (7)
C1—Co2i	2.467 (4)	C21—N2	1.357 (6)
C2—C3	1.381 (6)	C21—C22	1.437 (6)
C2—C7	1.402 (6)	C22—N1	1.358 (5)
C3—C4	1.379 (6)	C22—C23	1.399 (7)
C3—H3	0.9300	C23—C26	1.398 (7)
C4—C5	1.383 (6)	C23—C24	1.424 (7)
C4—H4	0.9300	C24—C25	1.337 (8)
C5—C6	1.389 (6)	C24—H24	0.9300
C5—C9	1.491 (5)	C25—H25	0.9300
C6—C7	1.390 (6)	C26—C27	1.354 (7)
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.509 (6)	C27—C28	1.389 (7)
C8—O3	1.229 (5)	C27—H27	0.9300
C8—O4	1.283 (5)	C28—N1	1.322 (6)
C9—C16	1.374 (6)	C28—H28	0.9300
C9—C10	1.386 (6)	Co1—O5ii	2.001 (3)
C10—C11	1.393 (6)	Co1—N1	2.108 (4)
C10—H10	0.9300	Co1—O8iii	2.117 (3)
C11—C12	1.373 (6)	Co1—N2	2.143 (4)
C11—H11	0.9300	Co1—O10	2.144 (3)
C12—C14	1.388 (6)	Co1—O4	2.149 (3)
C12—C13	1.508 (6)	Co2—O6ii	2.025 (3)
C13—O7	1.241 (5)	Co2—O4	2.080 (3)
C13—O8	1.273 (5)	Co2—O1i	2.088 (3)
C14—C16	1.387 (6)	Co2—O9	2.127 (3)
C14—C15	1.493 (6)	Co2—O2i	2.184 (3)
C15—O5	1.253 (5)	Co2—O8iii	2.210 (3)
C15—O6	1.269 (5)	Co2—C1i	2.467 (4)
C16—H16	0.9300	O9—H9A	0.8500
C17—N2	1.318 (6)	O9—H9B	0.8499
C17—C18	1.399 (6)	O10—H10A	0.8499
C17—H17	0.9300	O10—H10B	0.8501
C18—C19	1.359 (8)	O11—H11A	0.8520
C18—H18	0.9300	O11—H11B	0.8548
C19—C20	1.402 (7)
O2—C1—O1	119.9 (4)	C25—C24—H24	119.3
O2—C1—C2	119.5 (4)	C23—C24—H24	119.3
O1—C1—C2	120.6 (4)	C24—C25—C20	121.3 (5)
O2—C1—Co2i	62.1 (2)	C24—C25—H25	119.3
O1—C1—Co2i	57.8 (2)	C20—C25—H25	119.3
C2—C1—Co2i	177.7 (3)	C27—C26—C23	120.1 (5)
C3—C2—C7	118.1 (4)	C27—C26—H26	119.9
C3—C2—C1	119.1 (4)	C23—C26—H26	119.9
C7—C2—C1	122.6 (4)	C26—C27—C28	119.6 (5)
C4—C3—C2	121.7 (4)	C26—C27—H27	120.2
C4—C3—H3	119.1	C28—C27—H27	120.2
C2—C3—H3	119.1	N1—C28—C27	122.6 (5)
C3—C4—C5	121.6 (4)	N1—C28—H28	118.7
C3—C4—H4	119.2	C27—C28—H28	118.7
C5—C4—H4	119.2	O5ii—Co1—N1	161.87 (14)
C4—C5—C6	116.5 (4)	O5ii—Co1—O8iii	97.71 (11)
C4—C5—C9	121.9 (4)	N1—Co1—O8iii	96.93 (13)
C6—C5—C9	121.6 (4)	O5ii—Co1—N2	88.47 (13)
C5—C6—C7	123.2 (4)	N1—Co1—N2	77.93 (14)
C5—C6—H6	118.4	O8iii—Co1—N2	172.24 (13)
C7—C6—H6	118.4	O5ii—Co1—O10	86.77 (13)
C6—C7—C2	118.9 (4)	N1—Co1—O10	104.03 (14)
C6—C7—C8	116.8 (4)	O8iii—Co1—O10	89.41 (11)
C2—C7—C8	124.2 (4)	N2—Co1—O10	86.25 (13)
O3—C8—O4	124.7 (4)	O5ii—Co1—O4	87.22 (13)
O3—C8—C7	117.0 (4)	N1—Co1—O4	86.00 (14)
O4—C8—C7	118.2 (4)	O8iii—Co1—O4	76.00 (11)
C16—C9—C10	117.5 (4)	N2—Co1—O4	109.13 (13)
C16—C9—C5	121.9 (4)	O10—Co1—O4	163.32 (11)
C10—C9—C5	120.6 (4)	O6ii—Co2—O4	98.38 (11)
C9—C10—C11	121.0 (4)	O6ii—Co2—O1i	153.17 (12)
C9—C10—H10	119.5	O4—Co2—O1i	107.16 (12)
C11—C10—H10	119.5	O6ii—Co2—O9	89.10 (13)
C12—C11—C10	120.7 (4)	O4—Co2—O9	93.31 (12)
C12—C11—H11	119.7	O1i—Co2—O9	97.35 (13)
C10—C11—H11	119.7	O6ii—Co2—O2i	93.38 (11)
C11—C12—C14	119.0 (4)	O4—Co2—O2i	168.19 (12)
C11—C12—C13	116.7 (4)	O1i—Co2—O2i	61.42 (11)
C14—C12—C13	124.3 (4)	O9—Co2—O2i	85.65 (12)
O7—C13—O8	124.2 (4)	O6ii—Co2—O8iii	89.12 (12)
O7—C13—C12	116.5 (4)	O4—Co2—O8iii	75.45 (11)
O8—C13—C12	119.0 (4)	O1i—Co2—O8iii	89.44 (12)
C16—C14—C12	119.4 (4)	O9—Co2—O8iii	168.23 (11)
C16—C14—C15	117.9 (4)	O2i—Co2—O8iii	106.07 (12)
C12—C14—C15	122.6 (4)	O6ii—Co2—C1i	123.70 (13)
O5—C15—O6	125.4 (4)	O4—Co2—C1i	137.77 (14)
O5—C15—C14	117.5 (4)	O1i—Co2—C1i	30.76 (13)
O6—C15—C14	117.0 (4)	O9—Co2—C1i	90.96 (13)
C9—C16—C14	122.4 (4)	O2i—Co2—C1i	30.68 (13)
C9—C16—H16	118.8	O8iii—Co2—C1i	99.70 (13)
C14—C16—H16	118.8	C28—N1—C22	117.8 (4)
N2—C17—C18	123.2 (5)	C28—N1—Co1	127.4 (3)
N2—C17—H17	118.4	C22—N1—Co1	114.3 (3)
C18—C17—H17	118.4	C17—N2—C21	117.7 (4)
C19—C18—C17	119.3 (5)	C17—N2—Co1	128.8 (3)
C19—C18—H18	120.4	C21—N2—Co1	113.5 (3)
C17—C18—H18	120.4	C1—O1—Co2i	91.4 (3)
C18—C19—C20	119.6 (5)	C1—O2—Co2i	87.2 (3)
C18—C19—H19	120.2	C8—O4—Co2	125.8 (3)
C20—C19—H19	120.2	C8—O4—Co1	128.5 (3)
C19—C20—C21	117.1 (5)	Co2—O4—Co1	98.35 (12)
C19—C20—C25	124.6 (5)	C15—O5—Co1ii	131.1 (3)
C21—C20—C25	118.3 (5)	C15—O6—Co2ii	127.3 (3)
N2—C21—C20	123.1 (5)	C13—O8—Co1iv	121.5 (3)
N2—C21—C22	116.8 (4)	C13—O8—Co2iv	142.9 (3)
C20—C21—C22	120.1 (5)	Co1iv—O8—Co2iv	95.37 (11)
N1—C22—C23	123.3 (5)	Co2—O9—H9A	128.0
N1—C22—C21	117.4 (4)	Co2—O9—H9B	124.2
C23—C22—C21	119.3 (4)	H9A—O9—H9B	107.7
C26—C23—C22	116.5 (5)	Co1—O10—H10A	123.2
C26—C23—C24	124.1 (5)	Co1—O10—H10B	113.4
C22—C23—C24	119.4 (5)	H10A—O10—H10B	107.7
C25—C24—C23	121.4 (5)	H11A—O11—H11B	107.1
O2—C1—C2—C3	6.6 (7)	C26—C27—C28—N1	−1.6 (9)
O1—C1—C2—C3	−172.6 (4)	C27—C28—N1—C22	2.8 (8)
O2—C1—C2—C7	−178.3 (4)	C27—C28—N1—Co1	174.4 (4)
O1—C1—C2—C7	2.5 (7)	C23—C22—N1—C28	−3.7 (7)
C7—C2—C3—C4	1.1 (7)	C21—C22—N1—C28	173.6 (4)
C1—C2—C3—C4	176.4 (4)	C23—C22—N1—Co1	−176.4 (4)
C2—C3—C4—C5	0.5 (8)	C21—C22—N1—Co1	0.9 (5)
C3—C4—C5—C6	−1.4 (7)	O5ii—Co1—N1—C28	−129.0 (5)
C3—C4—C5—C9	179.3 (4)	O8iii—Co1—N1—C28	14.7 (4)
C4—C5—C6—C7	0.6 (7)	N2—Co1—N1—C28	−171.2 (5)
C9—C5—C6—C7	179.9 (4)	O10—Co1—N1—C28	105.8 (4)
C5—C6—C7—C2	1.0 (7)	O4—Co1—N1—C28	−60.7 (4)
C5—C6—C7—C8	−175.6 (4)	O5ii—Co1—N1—C22	42.8 (6)
C3—C2—C7—C6	−1.9 (7)	O8iii—Co1—N1—C22	−173.5 (3)
C1—C2—C7—C6	−176.9 (4)	N2—Co1—N1—C22	0.6 (3)
C3—C2—C7—C8	174.5 (4)	O10—Co1—N1—C22	−82.4 (3)
C1—C2—C7—C8	−0.6 (7)	O4—Co1—N1—C22	111.2 (3)
C6—C7—C8—O3	68.8 (6)	C18—C17—N2—C21	−0.8 (7)
C2—C7—C8—O3	−107.7 (5)	C18—C17—N2—Co1	176.4 (4)
C6—C7—C8—O4	−109.2 (5)	C20—C21—N2—C17	−0.4 (7)
C2—C7—C8—O4	74.4 (6)	C22—C21—N2—C17	−179.0 (4)
C4—C5—C9—C16	168.3 (5)	C20—C21—N2—Co1	−178.1 (4)
C6—C5—C9—C16	−10.9 (7)	C22—C21—N2—Co1	3.3 (5)
C4—C5—C9—C10	−9.3 (7)	O5ii—Co1—N2—C17	12.6 (4)
C6—C5—C9—C10	171.5 (4)	N1—Co1—N2—C17	−179.5 (5)
C16—C9—C10—C11	0.6 (7)	O10—Co1—N2—C17	−74.3 (4)
C5—C9—C10—C11	178.3 (4)	O4—Co1—N2—C17	99.1 (4)
C9—C10—C11—C12	−0.8 (8)	O5ii—Co1—N2—C21	−170.1 (3)
C10—C11—C12—C14	1.1 (7)	N1—Co1—N2—C21	−2.1 (3)
C10—C11—C12—C13	−178.9 (4)	O10—Co1—N2—C21	103.1 (3)
C11—C12—C13—O7	−65.5 (6)	O4—Co1—N2—C21	−83.5 (3)
C14—C12—C13—O7	114.5 (5)	O2—C1—O1—Co2i	2.7 (4)
C11—C12—C13—O8	108.9 (5)	C2—C1—O1—Co2i	−178.1 (4)
C14—C12—C13—O8	−71.1 (6)	O1—C1—O2—Co2i	−2.6 (4)
C11—C12—C14—C16	−1.2 (7)	C2—C1—O2—Co2i	178.2 (4)
C13—C12—C14—C16	178.8 (4)	O3—C8—O4—Co2	28.2 (6)
C11—C12—C14—C15	177.6 (4)	C7—C8—O4—Co2	−154.1 (3)
C13—C12—C14—C15	−2.4 (7)	O3—C8—O4—Co1	−115.2 (4)
C16—C14—C15—O5	−21.1 (6)	C7—C8—O4—Co1	62.6 (5)
C12—C14—C15—O5	160.0 (4)	O6ii—Co2—O4—C8	−93.6 (3)
C16—C14—C15—O6	157.3 (4)	O1i—Co2—O4—C8	94.8 (3)
C12—C14—C15—O6	−21.6 (7)	O9—Co2—O4—C8	−4.0 (3)
C10—C9—C16—C14	−0.8 (7)	O2i—Co2—O4—C8	80.6 (7)
C5—C9—C16—C14	−178.5 (4)	O8iii—Co2—O4—C8	179.6 (3)
C12—C14—C16—C9	1.1 (7)	C1i—Co2—O4—C8	91.1 (4)
C15—C14—C16—C9	−177.8 (4)	O6ii—Co2—O4—Co1	58.29 (14)
N2—C17—C18—C19	1.0 (8)	O1i—Co2—O4—Co1	−113.39 (13)
C17—C18—C19—C20	0.0 (8)	O9—Co2—O4—Co1	147.87 (13)
C18—C19—C20—C21	−1.1 (8)	O2i—Co2—O4—Co1	−127.6 (6)
C18—C19—C20—C25	177.9 (5)	O8iii—Co2—O4—Co1	−28.59 (11)
C19—C20—C21—N2	1.4 (7)	C1i—Co2—O4—Co1	−117.05 (18)
C25—C20—C21—N2	−177.8 (5)	O5ii—Co1—O4—C8	82.0 (4)
C19—C20—C21—C22	179.9 (4)	N1—Co1—O4—C8	−81.2 (4)
C25—C20—C21—C22	0.8 (7)	O8iii—Co1—O4—C8	−179.4 (4)
N2—C21—C22—N1	−2.9 (6)	N2—Co1—O4—C8	−5.5 (4)
C20—C21—C22—N1	178.4 (4)	O10—Co1—O4—C8	150.9 (4)
N2—C21—C22—C23	174.5 (5)	O5ii—Co1—O4—Co2	−68.77 (12)
C20—C21—C22—C23	−4.1 (7)	N1—Co1—O4—Co2	128.06 (14)
N1—C22—C23—C26	3.2 (8)	O8iii—Co1—O4—Co2	29.89 (11)
C21—C22—C23—C26	−174.1 (5)	N2—Co1—O4—Co2	−156.19 (13)
N1—C22—C23—C24	−178.6 (5)	O10—Co1—O4—Co2	0.2 (5)
C21—C22—C23—C24	4.2 (8)	O6—C15—O5—Co1ii	16.8 (7)
C26—C23—C24—C25	177.3 (6)	C14—C15—O5—Co1ii	−165.0 (3)
C22—C23—C24—C25	−0.8 (9)	O5—C15—O6—Co2ii	10.6 (7)
C23—C24—C25—C20	−2.6 (9)	C14—C15—O6—Co2ii	−167.6 (3)
C19—C20—C25—C24	−176.4 (5)	O7—C13—O8—Co1iv	3.7 (6)
C21—C20—C25—C24	2.6 (8)	C12—C13—O8—Co1iv	−170.3 (3)
C22—C23—C26—C27	−1.8 (9)	O7—C13—O8—Co2iv	176.9 (3)
C24—C23—C26—C27	−180.0 (6)	C12—C13—O8—Co2iv	3.0 (7)
C23—C26—C27—C28	1.1 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11B···O7ii	0.85	2.04	2.886 (6)	173.
O11—H11A···O7v	0.85	2.15	2.931 (5)	152.
O10—H10B···O7iii	0.85	2.20	2.668 (4)	115.
O10—H10A···O2vi	0.85	1.95	2.756 (4)	159.
O9—H9A···O3	0.85	2.09	2.661 (4)	124.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11B⋯O7i	0.85	2.04	2.886 (6)	173
O11—H11A⋯O7ii	0.85	2.15	2.931 (5)	152
O10—H10B⋯O7iii	0.85	2.20	2.668 (4)	115
O10—H10A⋯O2iv	0.85	1.95	2.756 (4)	159
O9—H9A⋯O3	0.85	2.09	2.661 (4)	124

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