Crystal structure of poly[[{μ2-1,4-bis[(1H-imid­azol-1-yl)methyl]benzene}[μ6-5-(4-carboxylatophenoxy)isophthalato]-μ3-hydroxido-dicobalt(II)] 0.25-hydrate]

Li, Y.; Sun, D.; Ming, J.; Han, L.; Su, G.

doi:10.1107/S1600536814022806

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages m376-m377

doi:10.1107/S1600536814022806

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Crystal structure of poly[[{μ₂-1,4-bis[(1H-imidazol-1-yl)methyl]benzene}[μ₆-5-(4-carboxylatophenoxy)isophthalato]-μ₃-hydroxido-dicobalt(II)] 0.25-hydrate]

Yaping Li,^a Dajun Sun,^b ^* Julia Ming,^c Liying Han ^d and Guanfang Su ^a

^aDepartment of Ophthalmology, The Second Hospital of Jilin University, 218 Ziqiang Street, Changchun, 130041, Jilin Province, People's Republic of China, ^bDepartment of Vascular Surgery, The China–Japan Union Hospital of Jilin University, 126 Xiantai Street, Changchun, 130033, Jilin Province, People's Republic of China, ^cSt Erik's Eye Hospital, Karolinska Institutet, Polhemsgatan 50, SE-112-82, Stockholm, Sweden, and ^dDepartment of Gynaecology, The Second Hospital of Jilin University, 218 Ziqiang Street, Changchun, 130041, Jilin Province, People's Republic of China
^*Correspondence e-mail: sundajun2014@163.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 24 July 2014; accepted 17 October 2014; online 29 October 2014)

The title coordination polymer, {[Co₂(C₁₅H₇O₇)(OH)(C₁₄H₁₄N₄)]·0.25H₂O}_n, was synthesized under hydrothermal conditions. The asymmetric unit contains two Co²⁺ ions, one L³⁻ anion originating from 5-(4-carboxyphenoxy)isophthalic acid (H₃L), one OH⁻ ligand, one 1,4-bis[(1H-imidazol-l-yl)methyl]benzene (bix) ligand and one disordered lattice water molecule (occupancy 0.25). The two Co²⁺ ions have different environments. One has an octahedral O₄N₂ coordination sphere, defined by four O atoms from three carboxylate groups and one OH⁻ ligand, and two N atoms from two symmetry-related bix ligands. The other has a trigonal-bipyramidal O₅ coordination sphere resulting from three carboxylate groups and two OH⁻ ligands. The dihedral angles between the two benzene rings in the L³⁻ ligand and between the benzene ring and the two imidazole rings in the bix ligand are 67.05 (15), 75.27 (17) and 82.05 (17)°, respectively. Four neighbouring Co²⁺ ions are linked by six carboxylate groups and two μ₃-OH ligands, forming a butterfly-shaped secondary building unit (SBU). These SBUs are connected by L³⁻ anions into layers parallel to (1-10). Adjacent layers are cross-linked by the bix ligands, forming a three-dimensional framework that has a bimodal (3,8)-connected tfz-d topology. The disordered lattice water molecule is located in the voids of the framework and has O⋯O and O⋯N contacts of 2.81 (2) and 2.95 (2) Å, suggesting medium-strength hydrogen bonds. The title compound may be a good candidate for artificial eye lenses.

Keywords: crystal structure; Co^II complex; (3,8)-connected tfz-d topology.

CCDC reference: 1029647

1. Related literature

For general background to the properties and applications of compounds with metal-organic framework structures (MOFs), see: Batten & Robson (1998 ); Farrusseng et al. (2009 ); Iremonger et al. (2013 ); Kreno et al. (2012 ); Kurmoo (2009 ); Song et al. (2013 ); Su et al. (2012 ); Wong et al. (2006 ). For topological analysis of crystal structures, see: Blatov et al. (2010 ).

2. Experimental

2.1. Crystal data

[Co₂(C₁₅H₇O₇)(OH)(C₁₄H₁₄N₄)]·0.25H₂O
M_r = 676.87
Triclinic, $[P \overline 1]$
a = 10.7381 (6) Å
b = 10.7477 (6) Å
c = 13.5585 (12) Å
α = 95.596 (1)°
β = 91.497 (1)°
γ = 118.728 (1)°
V = 1360.85 (16) Å³
Z = 2
Mo Kα radiation
μ = 1.28 mm⁻¹
T = 173 K
0.19 × 0.16 × 0.15 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2010 ) T_min = 0.793, T_max = 0.831
7626 measured reflections
5314 independent reflections
4359 reflections with I > 2σ(I)
R_int = 0.024

2.3. Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.086
S = 1.04
5314 reflections
396 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Putz, 2010 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1029647

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814022806/wm5040sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814022806/wm5040Isup2.hkl

checkCIF report

Synthesis and crystallization top

A mixture of cobalt acetate tetrahydrate (0.0249 g, 0.1 mmol), 5-(4-carboxyphenoxy)isophthalic acid (H₃L, 0.0151 g, 0.05 mmol), 1,4-bis[(1H-imidazol-l-yl)methyl]benzene (bix) (0.0118 g, 0.05 mmol), water (6 ml) and NaOH (aq, 0.1 molar, 2 ml) was placed in a 20 ml PTFE-lined stainless steel vessel under autogenous pressure, heated at a 413 K for 5 days, and allowed to cool down to room temperature during 30 h. The obtained crystals were collected, washed with water and ethanol, and dried under ambient conditions with a yield of 17% based on cobalt acetate.

Refinement top

H atoms attached to C atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with a C—H distance of 0.95 Å (aromatic) and 0.98 Å (methylene), and with U_iso(H) = 1.2U_eq(C). The H atom of the hydroxy group was located from a difference Fourier map and was refined with a distance restraint of 0.85 (2) Å. Additional electron density was found that was assigned to a lattice water molecule. Refinement of its occupancy revealed a considerable under-occupation that was fixed at 0.25 for the final refinement. H atoms of this molecule were not considered in the final model.

Related literature top

For general background to the properties and applications of compounds with metal-organic framework structures (MOFs), see: Batten & Robson (1998); Farrusseng et al. (2009); Iremonger et al. (2013); Kreno et al. (2012); Kurmoo (2009); Song et al. (2013); Su et al. (2012); Wong et al. (2006). For topological analysis of crystal structures, see: Blatov et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Putz, 2010); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

The extended asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. The disordered lattice water molecule has been omitted for clarity. [Symmetry codes: i) 2 - x, 2 - y, 1 - z; ii) 2 - x, 1 - y, 1 - z; iii) -1 + x, -1 + y, z; iv) 2 - x, 2 - y, -z; v) 1 - x, 1 - y, z.]

The tetranuclear SBU in the structure of the title compound. [Symmetry code: A) 1 - x,1 - y,-z.]

View of the layered network formed by the SBUs and the L^3- anions.

Poly[[{µ₂-1,4-bis[(1H-imidazol-1-yl)methyl]benzene}[µ₆-5-(4-carboxylatophenoxy)isophthalato]-µ₃-hydroxido-dicobalt(II)] 0.25-hydrate] top

Crystal data top

[Co₂(C₁₅H₇O₇)(OH)(C₁₄H₁₄N₄)]·0.25H₂O	V = 1360.85 (16) Å³
M_r = 676.87	Z = 2
Triclinic, P1	F(000) = 688
Hall symbol: -P 1	D_x = 1.651 Mg m⁻³
a = 10.7381 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7477 (6) Å	µ = 1.28 mm⁻¹
c = 13.5585 (12) Å	T = 173 K
α = 95.596 (1)°	Block, red
β = 91.497 (1)°	0.19 × 0.16 × 0.15 mm
γ = 118.728 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5314 independent reflections
Radiation source: fine-focus sealed tube	4359 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 26.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2010)	h = −13→7
T_min = 0.793, T_max = 0.831	k = −12→13
7626 measured reflections	l = −16→15

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.038P)² + 0.1129P] where P = (F_o² + 2F_c²)/3
5314 reflections	(Δ/σ)_max = 0.001
396 parameters	Δρ_max = 0.37 e Å⁻³
1 restraint	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Co₂(C₁₅H₇O₇)(OH)(C₁₄H₁₄N₄)]·0.25H₂O	γ = 118.728 (1)°
M_r = 676.87	V = 1360.85 (16) Å³
Triclinic, P1	Z = 2
a = 10.7381 (6) Å	Mo Kα radiation
b = 10.7477 (6) Å	µ = 1.28 mm⁻¹
c = 13.5585 (12) Å	T = 173 K
α = 95.596 (1)°	0.19 × 0.16 × 0.15 mm
β = 91.497 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5314 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2010)	4359 reflections with I > 2σ(I)
T_min = 0.793, T_max = 0.831	R_int = 0.024
7626 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	1 restraint
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.37 e Å⁻³
5314 reflections	Δρ_min = −0.37 e Å⁻³
396 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C4	1.2218 (3)	0.9155 (3)	0.33134 (18)	0.0184 (6)
C5	1.3041 (3)	1.0414 (3)	0.29083 (18)	0.0174 (6)
H5	1.3904	1.1145	0.3255	0.021*
C6	1.2583 (3)	1.0586 (3)	0.19865 (18)	0.0142 (5)
C7	1.1319 (3)	0.9514 (3)	0.14908 (18)	0.0149 (5)
H7	1.0997	0.9645	0.0870	0.018*
C8	1.3462 (3)	1.1946 (3)	0.15375 (18)	0.0159 (5)
C9	1.2867 (3)	0.9886 (3)	0.50570 (18)	0.0189 (6)
C10	1.2320 (3)	1.0822 (3)	0.5104 (2)	0.0260 (6)
H10	1.1758	1.0828	0.4553	0.031*
C11	1.2605 (3)	1.1752 (3)	0.5968 (2)	0.0235 (6)
H11	1.2248	1.2409	0.5998	0.028*
C12	1.3400 (3)	1.1742 (3)	0.67892 (19)	0.0191 (6)
C13	1.3897 (3)	1.0762 (3)	0.67393 (19)	0.0217 (6)
H13	1.4413	1.0720	0.7303	0.026*
C14	1.3646 (3)	0.9841 (3)	0.58730 (19)	0.0217 (6)
H14	1.4005	0.9186	0.5839	0.026*
C15	1.3742 (3)	1.2825 (3)	0.76871 (19)	0.0186 (6)
C16	0.8332 (3)	0.2942 (3)	0.1162 (2)	0.0271 (7)
H16	0.9160	0.3856	0.1245	0.033*
C17	0.6168 (3)	0.1286 (3)	0.0961 (2)	0.0338 (7)
H17	0.5157	0.0803	0.0878	0.041*
C18	0.6975 (3)	0.0639 (3)	0.0971 (2)	0.0339 (7)
H18	0.6645	−0.0361	0.0897	0.041*
C19	0.9626 (3)	0.1515 (3)	0.1249 (2)	0.0323 (7)
H19A	1.0080	0.1586	0.0616	0.039*
H19B	0.9334	0.0554	0.1444	0.039*
C20	1.0678 (3)	0.2645 (3)	0.2043 (2)	0.0287 (7)
C21	1.1660 (3)	0.3964 (4)	0.1793 (2)	0.0356 (8)
H21	1.1718	0.4114	0.1113	0.043*
C22	1.2558 (3)	0.5068 (4)	0.2509 (2)	0.0343 (8)
H22	1.3203	0.5975	0.2321	0.041*
C23	1.2520 (3)	0.4855 (3)	0.3500 (2)	0.0281 (7)
C24	1.1572 (3)	0.3524 (3)	0.3759 (2)	0.0342 (8)
H24	1.1557	0.3360	0.4435	0.041*
C25	1.0645 (3)	0.2427 (3)	0.3038 (2)	0.0345 (7)
H25	0.9986	0.1526	0.3226	0.041*
C26	1.3528 (3)	0.6094 (3)	0.4265 (2)	0.0342 (8)
H26A	1.4452	0.6102	0.4324	0.041*
H26B	1.3701	0.7002	0.4029	0.041*
C27	1.3559 (3)	0.5860 (3)	0.6085 (2)	0.0255 (6)
H27	1.4409	0.5794	0.6127	0.031*
C28	1.1671 (3)	0.5928 (3)	0.6463 (2)	0.0288 (7)
H28	1.0927	0.5913	0.6835	0.035*
C29	1.1776 (3)	0.6075 (3)	0.5482 (2)	0.0315 (7)
H29	1.1141	0.6190	0.5047	0.038*
N3	1.2798 (2)	0.5803 (2)	0.68379 (16)	0.0221 (5)
N4	1.2985 (3)	0.6023 (3)	0.52460 (17)	0.0277 (6)
O3	1.30271 (18)	1.19794 (18)	0.06670 (12)	0.0196 (4)
O4	1.45267 (18)	1.29275 (18)	0.20484 (13)	0.0215 (4)
O5	1.2654 (2)	0.89221 (18)	0.42257 (12)	0.0223 (4)
O6	1.4105 (2)	1.25737 (19)	0.85136 (13)	0.0226 (4)
O7	1.3637 (2)	1.39052 (19)	0.75613 (13)	0.0248 (4)
O8	0.58483 (19)	0.45012 (18)	0.02893 (13)	0.0166 (4)
O1W	1.333 (2)	0.746 (2)	0.1092 (16)	0.165 (8)*	0.25
H8O	0.632 (3)	0.422 (3)	−0.0057 (19)	0.030 (9)*
C1	0.9122 (3)	0.7102 (3)	0.13668 (18)	0.0178 (6)
C2	1.0516 (3)	0.8247 (3)	0.18914 (18)	0.0164 (5)
C3	1.0979 (3)	0.8066 (3)	0.28083 (19)	0.0186 (6)
H3	1.0445	0.7200	0.3085	0.022*
N1	0.7019 (2)	0.2740 (2)	0.10884 (17)	0.0235 (5)
N2	0.8355 (2)	0.1701 (2)	0.11079 (16)	0.0225 (5)
O1	0.86795 (18)	0.58516 (18)	0.15727 (14)	0.0230 (4)
O2	0.84879 (19)	0.74906 (19)	0.07745 (13)	0.0236 (4)
Co1	0.65561 (4)	0.43648 (3)	0.16976 (2)	0.01604 (10)
Co2	0.63498 (4)	0.65449 (3)	0.02558 (2)	0.01564 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C4	0.0237 (14)	0.0168 (13)	0.0139 (13)	0.0096 (12)	−0.0039 (11)	0.0018 (11)
C5	0.0176 (13)	0.0149 (13)	0.0162 (13)	0.0058 (11)	−0.0041 (11)	−0.0010 (10)
C6	0.0146 (13)	0.0114 (12)	0.0153 (13)	0.0053 (10)	0.0013 (10)	0.0016 (10)
C7	0.0168 (13)	0.0147 (13)	0.0134 (12)	0.0080 (11)	−0.0032 (10)	0.0016 (10)
C8	0.0151 (13)	0.0157 (13)	0.0169 (13)	0.0077 (11)	−0.0019 (11)	0.0019 (11)
C9	0.0240 (14)	0.0160 (13)	0.0120 (13)	0.0065 (12)	−0.0025 (11)	0.0009 (10)
C10	0.0348 (17)	0.0297 (16)	0.0174 (14)	0.0195 (14)	−0.0073 (12)	0.0004 (12)
C11	0.0288 (16)	0.0224 (15)	0.0230 (14)	0.0159 (13)	−0.0035 (12)	0.0021 (12)
C12	0.0225 (14)	0.0146 (13)	0.0156 (13)	0.0054 (11)	−0.0009 (11)	0.0024 (11)
C13	0.0248 (15)	0.0229 (15)	0.0165 (13)	0.0111 (12)	−0.0050 (11)	0.0027 (11)
C14	0.0299 (16)	0.0211 (14)	0.0171 (14)	0.0155 (13)	−0.0063 (12)	0.0006 (11)
C15	0.0163 (13)	0.0167 (14)	0.0185 (14)	0.0045 (11)	0.0002 (11)	0.0035 (11)
C16	0.0248 (16)	0.0171 (14)	0.0359 (17)	0.0082 (13)	−0.0020 (13)	−0.0008 (13)
C17	0.0245 (16)	0.0193 (15)	0.051 (2)	0.0075 (13)	0.0014 (14)	−0.0042 (14)
C18	0.0354 (18)	0.0161 (15)	0.047 (2)	0.0097 (14)	0.0055 (15)	0.0023 (14)
C19	0.0388 (18)	0.0387 (18)	0.0306 (17)	0.0297 (16)	−0.0061 (14)	−0.0051 (14)
C20	0.0317 (17)	0.0363 (18)	0.0267 (16)	0.0252 (15)	−0.0032 (13)	−0.0060 (13)
C21	0.0322 (18)	0.060 (2)	0.0190 (15)	0.0266 (17)	0.0005 (13)	0.0028 (15)
C22	0.0253 (17)	0.044 (2)	0.0289 (17)	0.0129 (15)	0.0007 (13)	0.0078 (15)
C23	0.0265 (16)	0.0365 (18)	0.0230 (15)	0.0165 (14)	0.0007 (12)	0.0045 (13)
C24	0.046 (2)	0.0370 (18)	0.0225 (16)	0.0226 (16)	−0.0071 (14)	0.0034 (14)
C25	0.044 (2)	0.0308 (17)	0.0320 (17)	0.0221 (16)	−0.0051 (15)	0.0015 (14)
C26	0.0279 (17)	0.0392 (19)	0.0248 (16)	0.0075 (15)	−0.0015 (13)	0.0070 (14)
C27	0.0231 (15)	0.0245 (15)	0.0243 (15)	0.0087 (13)	−0.0089 (12)	0.0015 (12)
C28	0.0274 (16)	0.0282 (16)	0.0300 (16)	0.0126 (14)	−0.0033 (13)	0.0064 (13)
C29	0.0261 (16)	0.0342 (18)	0.0313 (17)	0.0121 (14)	−0.0063 (13)	0.0083 (14)
N3	0.0227 (13)	0.0186 (12)	0.0223 (12)	0.0084 (10)	−0.0047 (10)	0.0019 (10)
N4	0.0277 (14)	0.0245 (13)	0.0230 (13)	0.0066 (11)	−0.0042 (10)	0.0035 (10)
O3	0.0197 (10)	0.0154 (9)	0.0169 (9)	0.0028 (8)	−0.0040 (8)	0.0057 (8)
O4	0.0186 (10)	0.0165 (10)	0.0182 (9)	0.0000 (8)	−0.0043 (8)	0.0018 (8)
O5	0.0359 (12)	0.0168 (10)	0.0123 (9)	0.0119 (9)	−0.0070 (8)	0.0007 (7)
O6	0.0324 (11)	0.0194 (10)	0.0159 (9)	0.0133 (9)	−0.0044 (8)	−0.0009 (8)
O7	0.0352 (12)	0.0159 (10)	0.0236 (10)	0.0131 (9)	−0.0012 (9)	0.0006 (8)
O8	0.0170 (10)	0.0111 (9)	0.0185 (9)	0.0046 (8)	−0.0016 (8)	0.0006 (7)
C1	0.0170 (13)	0.0163 (14)	0.0152 (13)	0.0042 (11)	0.0010 (11)	0.0027 (11)
C2	0.0172 (13)	0.0141 (13)	0.0160 (13)	0.0062 (11)	0.0000 (11)	0.0018 (10)
C3	0.0218 (14)	0.0137 (13)	0.0182 (13)	0.0069 (11)	−0.0001 (11)	0.0033 (11)
N1	0.0225 (12)	0.0168 (12)	0.0292 (13)	0.0086 (10)	−0.0038 (10)	0.0005 (10)
N2	0.0278 (13)	0.0208 (12)	0.0219 (12)	0.0155 (11)	−0.0028 (10)	−0.0028 (10)
O1	0.0160 (10)	0.0139 (9)	0.0337 (11)	0.0030 (8)	−0.0038 (8)	0.0049 (8)
O2	0.0169 (10)	0.0174 (10)	0.0257 (10)	−0.0009 (8)	−0.0063 (8)	0.0079 (8)
Co1	0.01564 (19)	0.01004 (18)	0.01836 (19)	0.00323 (15)	−0.00388 (14)	0.00201 (14)
Co2	0.01722 (19)	0.01009 (18)	0.01444 (18)	0.00264 (15)	−0.00307 (14)	0.00217 (14)

Geometric parameters (Å, º) top

C4—C3	1.381 (4)	C22—C23	1.383 (4)
C4—C5	1.391 (3)	C22—H22	0.9500
C4—O5	1.398 (3)	C23—C24	1.386 (4)
C5—C6	1.393 (3)	C23—C26	1.519 (4)
C5—H5	0.9500	C24—C25	1.390 (4)
C6—C7	1.386 (3)	C24—H24	0.9500
C6—C8	1.508 (3)	C25—H25	0.9500
C7—C2	1.390 (3)	C26—N4	1.460 (4)
C7—H7	0.9500	C26—H26A	0.9900
C8—O4	1.248 (3)	C26—H26B	0.9900
C8—O3	1.268 (3)	C27—N3	1.312 (4)
C9—C10	1.385 (4)	C27—N4	1.346 (3)
C9—C14	1.388 (3)	C27—H27	0.9500
C9—O5	1.388 (3)	C28—C29	1.357 (4)
C10—C11	1.386 (4)	C28—N3	1.371 (3)
C10—H10	0.9500	C28—H28	0.9500
C11—C12	1.390 (3)	C29—N4	1.370 (4)
C11—H11	0.9500	C29—H29	0.9500
C12—C13	1.388 (4)	N3—Co1ⁱ	2.139 (2)
C12—C15	1.504 (4)	O3—Co2ⁱⁱ	1.9848 (16)
C13—C14	1.390 (4)	O4—Co1ⁱⁱⁱ	2.0791 (17)
C13—H13	0.9500	O6—Co2^iv	2.0247 (18)
C14—H14	0.9500	O7—Co1^iv	2.1279 (19)
C15—O7	1.246 (3)	O8—Co2	2.0000 (17)
C15—O6	1.272 (3)	O8—Co1	2.0811 (17)
C16—N1	1.318 (4)	O8—Co2^v	2.1395 (18)
C16—N2	1.341 (3)	O8—H8O	0.839 (17)
C16—H16	0.9500	C1—O1	1.256 (3)
C17—C18	1.347 (4)	C1—O2	1.262 (3)
C17—N1	1.369 (4)	C1—C2	1.505 (3)
C17—H17	0.9500	C2—C3	1.392 (3)
C18—N2	1.360 (4)	C3—H3	0.9500
C18—H18	0.9500	N1—Co1	2.134 (2)
C19—N2	1.482 (3)	O1—Co1	2.0860 (17)
C19—C20	1.508 (4)	O2—Co2	2.0813 (18)
C19—H19A	0.9900	Co1—O4^vi	2.0791 (17)
C19—H19B	0.9900	Co1—O7^iv	2.1279 (19)
C20—C21	1.383 (4)	Co1—N3ⁱ	2.139 (2)
C20—C25	1.390 (4)	Co2—O3ⁱⁱ	1.9848 (16)
C21—C22	1.381 (4)	Co2—O6^iv	2.0247 (18)
C21—H21	0.9500	Co2—O8^v	2.1395 (18)

C3—C4—C5	121.2 (2)	N4—C26—H26B	108.9
C3—C4—O5	117.7 (2)	C23—C26—H26B	108.9
C5—C4—O5	120.9 (2)	H26A—C26—H26B	107.8
C4—C5—C6	119.0 (2)	N3—C27—N4	111.6 (3)
C4—C5—H5	120.5	N3—C27—H27	124.2
C6—C5—H5	120.5	N4—C27—H27	124.2
C7—C6—C5	119.9 (2)	C29—C28—N3	109.8 (3)
C7—C6—C8	120.4 (2)	C29—C28—H28	125.1
C5—C6—C8	119.7 (2)	N3—C28—H28	125.1
C6—C7—C2	120.7 (2)	C28—C29—N4	106.0 (3)
C6—C7—H7	119.6	C28—C29—H29	127.0
C2—C7—H7	119.6	N4—C29—H29	127.0
O4—C8—O3	126.2 (2)	C27—N3—C28	105.6 (2)
O4—C8—C6	118.0 (2)	C27—N3—Co1ⁱ	121.73 (19)
O3—C8—C6	115.9 (2)	C28—N3—Co1ⁱ	132.6 (2)
C10—C9—C14	120.6 (2)	C27—N4—C29	107.0 (2)
C10—C9—O5	123.5 (2)	C27—N4—C26	126.5 (3)
C14—C9—O5	115.8 (2)	C29—N4—C26	126.5 (2)
C9—C10—C11	119.0 (2)	C8—O3—Co2ⁱⁱ	134.31 (16)
C9—C10—H10	120.5	C8—O4—Co1ⁱⁱⁱ	132.65 (17)
C11—C10—H10	120.5	C9—O5—C4	118.20 (19)
C10—C11—C12	121.4 (3)	C15—O6—Co2^iv	115.77 (17)
C10—C11—H11	119.3	C15—O7—Co1^iv	144.04 (18)
C12—C11—H11	119.3	Co2—O8—Co1	106.75 (8)
C13—C12—C11	118.7 (2)	Co2—O8—Co2^v	100.27 (8)
C13—C12—C15	122.1 (2)	Co1—O8—Co2^v	123.61 (8)
C11—C12—C15	119.2 (2)	Co2—O8—H8O	116 (2)
C12—C13—C14	120.7 (2)	Co1—O8—H8O	99 (2)
C12—C13—H13	119.7	Co2^v—O8—H8O	112 (2)
C14—C13—H13	119.7	O1—C1—O2	125.9 (2)
C9—C14—C13	119.5 (3)	O1—C1—C2	117.1 (2)
C9—C14—H14	120.2	O2—C1—C2	117.0 (2)
C13—C14—H14	120.2	C7—C2—C3	119.5 (2)
O7—C15—O6	124.9 (2)	C7—C2—C1	120.6 (2)
O7—C15—C12	116.9 (2)	C3—C2—C1	119.8 (2)
O6—C15—C12	118.2 (2)	C4—C3—C2	119.6 (2)
N1—C16—N2	111.8 (2)	C4—C3—H3	120.2
N1—C16—H16	124.1	C2—C3—H3	120.2
N2—C16—H16	124.1	C16—N1—C17	104.8 (2)
C18—C17—N1	110.1 (3)	C16—N1—Co1	120.66 (19)
C18—C17—H17	125.0	C17—N1—Co1	129.3 (2)
N1—C17—H17	125.0	C16—N2—C18	106.8 (2)
C17—C18—N2	106.5 (2)	C16—N2—C19	126.8 (2)
C17—C18—H18	126.8	C18—N2—C19	126.2 (2)
N2—C18—H18	126.8	C1—O1—Co1	125.59 (17)
N2—C19—C20	110.2 (2)	C1—O2—Co2	130.90 (16)
N2—C19—H19A	109.6	O4^vi—Co1—O8	93.75 (7)
C20—C19—H19A	109.6	O4^vi—Co1—O1	171.43 (7)
N2—C19—H19B	109.6	O8—Co1—O1	94.52 (7)
C20—C19—H19B	109.6	O4^vi—Co1—O7^iv	90.30 (7)
H19A—C19—H19B	108.1	O8—Co1—O7^iv	95.87 (7)
C21—C20—C25	118.4 (3)	O1—Co1—O7^iv	86.61 (7)
C21—C20—C19	119.7 (3)	O4^vi—Co1—N1	94.34 (8)
C25—C20—C19	121.7 (3)	O8—Co1—N1	90.45 (8)
C22—C21—C20	121.5 (3)	O1—Co1—N1	87.85 (8)
C22—C21—H21	119.2	O7^iv—Co1—N1	171.91 (8)
C20—C21—H21	119.2	O4^vi—Co1—N3ⁱ	84.20 (8)
C21—C22—C23	120.0 (3)	O8—Co1—N3ⁱ	177.78 (8)
C21—C22—H22	120.0	O1—Co1—N3ⁱ	87.50 (8)
C23—C22—H22	120.0	O7^iv—Co1—N3ⁱ	83.32 (8)
C22—C23—C24	119.1 (3)	N1—Co1—N3ⁱ	90.55 (9)
C22—C23—C26	118.5 (3)	O3ⁱⁱ—Co2—O8	140.83 (8)
C24—C23—C26	122.5 (3)	O3ⁱⁱ—Co2—O6^iv	104.88 (7)
C23—C24—C25	120.7 (3)	O8—Co2—O6^iv	113.82 (7)
C23—C24—H24	119.7	O3ⁱⁱ—Co2—O2	86.27 (7)
C25—C24—H24	119.7	O8—Co2—O2	98.24 (7)
C20—C25—C24	120.2 (3)	O6^iv—Co2—O2	91.54 (8)
C20—C25—H25	119.9	O3ⁱⁱ—Co2—O8^v	94.91 (7)
C24—C25—H25	119.9	O8—Co2—O8^v	79.73 (8)
N4—C26—C23	113.2 (2)	O6^iv—Co2—O8^v	89.87 (7)
N4—C26—H26A	108.9	O2—Co2—O8^v	177.87 (7)
C23—C26—H26A	108.9

C3—C4—C5—C6	1.6 (4)	C6—C7—C2—C3	1.0 (4)
O5—C4—C5—C6	178.5 (2)	C6—C7—C2—C1	178.1 (2)
C4—C5—C6—C7	0.3 (4)	O1—C1—C2—C7	158.0 (2)
C4—C5—C6—C8	179.9 (2)	O2—C1—C2—C7	−23.4 (4)
C5—C6—C7—C2	−1.6 (4)	O1—C1—C2—C3	−24.9 (4)
C8—C6—C7—C2	178.8 (2)	O2—C1—C2—C3	153.7 (2)
C7—C6—C8—O4	174.1 (2)	C5—C4—C3—C2	−2.2 (4)
C5—C6—C8—O4	−5.5 (4)	O5—C4—C3—C2	−179.2 (2)
C7—C6—C8—O3	−5.3 (4)	C7—C2—C3—C4	0.9 (4)
C5—C6—C8—O3	175.1 (2)	C1—C2—C3—C4	−176.3 (2)
C14—C9—C10—C11	2.3 (4)	N2—C16—N1—C17	−1.2 (3)
O5—C9—C10—C11	−179.5 (2)	N2—C16—N1—Co1	155.63 (18)
C9—C10—C11—C12	−1.3 (4)	C18—C17—N1—C16	0.7 (4)
C10—C11—C12—C13	−0.9 (4)	C18—C17—N1—Co1	−153.4 (2)
C10—C11—C12—C15	176.8 (3)	N1—C16—N2—C18	1.2 (3)
C11—C12—C13—C14	2.2 (4)	N1—C16—N2—C19	−174.3 (3)
C15—C12—C13—C14	−175.4 (2)	C17—C18—N2—C16	−0.8 (3)
C10—C9—C14—C13	−1.0 (4)	C17—C18—N2—C19	174.8 (3)
O5—C9—C14—C13	−179.4 (2)	C20—C19—N2—C16	36.0 (4)
C12—C13—C14—C9	−1.3 (4)	C20—C19—N2—C18	−138.8 (3)
C13—C12—C15—O7	158.7 (3)	O2—C1—O1—Co1	−36.0 (4)
C11—C12—C15—O7	−18.9 (4)	C2—C1—O1—Co1	142.50 (19)
C13—C12—C15—O6	−21.7 (4)	O1—C1—O2—Co2	21.4 (4)
C11—C12—C15—O6	160.7 (2)	C2—C1—O2—Co2	−157.07 (18)
N1—C17—C18—N2	0.1 (4)	Co2—O8—Co1—O4^vi	119.02 (9)
N2—C19—C20—C21	−86.0 (3)	Co2^v—O8—Co1—O4^vi	3.95 (11)
N2—C19—C20—C25	90.5 (3)	Co2—O8—Co1—O1	−58.72 (9)
C25—C20—C21—C22	−2.4 (5)	Co2^v—O8—Co1—O1	−173.79 (10)
C19—C20—C21—C22	174.3 (3)	Co2—O8—Co1—O7^iv	28.33 (9)
C20—C21—C22—C23	2.0 (5)	Co2^v—O8—Co1—O7^iv	−86.74 (11)
C21—C22—C23—C24	0.1 (5)	Co2—O8—Co1—N1	−146.60 (9)
C21—C22—C23—C26	179.8 (3)	Co2^v—O8—Co1—N1	98.33 (11)
C22—C23—C24—C25	−1.8 (5)	Co2—O8—Co1—N3ⁱ	97 (2)
C26—C23—C24—C25	178.5 (3)	Co2^v—O8—Co1—N3ⁱ	−18 (2)
C21—C20—C25—C24	0.7 (5)	C1—O1—Co1—O4^vi	−109.8 (5)
C19—C20—C25—C24	−175.9 (3)	C1—O1—Co1—O8	54.9 (2)
C23—C24—C25—C20	1.4 (5)	C1—O1—Co1—O7^iv	−40.8 (2)
C22—C23—C26—N4	152.3 (3)	C1—O1—Co1—N1	145.2 (2)
C24—C23—C26—N4	−28.0 (4)	C1—O1—Co1—N3ⁱ	−124.2 (2)
N3—C28—C29—N4	0.7 (3)	C16—N1—Co1—O4^vi	−147.6 (2)
N4—C27—N3—C28	0.3 (3)	C17—N1—Co1—O4^vi	2.9 (3)
N4—C27—N3—Co1ⁱ	−177.40 (17)	C16—N1—Co1—O8	118.6 (2)
C29—C28—N3—C27	−0.6 (3)	C17—N1—Co1—O8	−90.9 (3)
C29—C28—N3—Co1ⁱ	176.76 (19)	C16—N1—Co1—O1	24.1 (2)
N3—C27—N4—C29	0.1 (3)	C17—N1—Co1—O1	174.6 (3)
N3—C27—N4—C26	−178.5 (3)	C16—N1—Co1—O7^iv	−22.8 (7)
C28—C29—N4—C27	−0.4 (3)	C17—N1—Co1—O7^iv	127.7 (5)
C28—C29—N4—C26	178.1 (3)	C16—N1—Co1—N3ⁱ	−63.4 (2)
C23—C26—N4—C27	115.6 (3)	C17—N1—Co1—N3ⁱ	87.1 (3)
C23—C26—N4—C29	−62.6 (4)	Co1—O8—Co2—O3ⁱⁱ	144.91 (9)
O4—C8—O3—Co2ⁱⁱ	−3.0 (4)	Co2^v—O8—Co2—O3ⁱⁱ	−85.14 (12)
C6—C8—O3—Co2ⁱⁱ	176.27 (17)	Co1—O8—Co2—O6^iv	−44.69 (10)
O3—C8—O4—Co1ⁱⁱⁱ	−39.8 (4)	Co2^v—O8—Co2—O6^iv	85.26 (9)
C6—C8—O4—Co1ⁱⁱⁱ	140.96 (19)	Co1—O8—Co2—O2	50.69 (9)
C10—C9—O5—C4	18.1 (4)	Co2^v—O8—Co2—O2	−179.37 (7)
C14—C9—O5—C4	−163.6 (2)	Co1—O8—Co2—O8^v	−129.95 (12)
C3—C4—O5—C9	−123.9 (3)	Co2^v—O8—Co2—O8^v	0.0
C5—C4—O5—C9	59.1 (3)	C1—O2—Co2—O3ⁱⁱ	−171.8 (2)
O7—C15—O6—Co2^iv	27.6 (3)	C1—O2—Co2—O8	−31.0 (2)
C12—C15—O6—Co2^iv	−151.95 (18)	C1—O2—Co2—O6^iv	83.4 (2)
O6—C15—O7—Co1^iv	−17.9 (5)	C1—O2—Co2—O8^v	−48 (2)
C12—C15—O7—Co1^iv	161.6 (2)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y+2, −z; (iii) x+1, y+1, z; (iv) −x+2, −y+2, −z+1; (v) −x+1, −y+1, −z; (vi) x−1, y−1, z.

Experimental details

Crystal data
Chemical formula	[Co₂(C₁₅H₇O₇)(OH)(C₁₄H₁₄N₄)]·0.25H₂O
M_r	676.87
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	10.7381 (6), 10.7477 (6), 13.5585 (12)
α, β, γ (°)	95.596 (1), 91.497 (1), 118.728 (1)
V (Å³)	1360.85 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.28
Crystal size (mm)	0.19 × 0.16 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2010)
T_min, T_max	0.793, 0.831
No. of measured, independent and observed [I > 2σ(I)] reflections	7626, 5314, 4359
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.086, 1.04
No. of reflections	5314
No. of parameters	396
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.37

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Putz, 2010), publCIF (Westrip, 2010).

Acknowledgements

The authors acknowledge the financial aid provided by the Natural Science Foundation of Jilin Province (201015168) and a project of the National Development and Reform Commission of Jilin Province.

References

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Volume 70| Part 11| November 2014| Pages m376-m377

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