Triaqua­(cyclo­hex-4-ene-1,2-dicarboxyl­ato-κO1)(1,10-phenanthroline-κ2N,N′)cobalt(II)

Li, H.-Y.; Wang, C.; Huang, F.-P.; Jiang, Y.-M.

doi:10.1107/S160053681204024X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages m1375-m1376

doi:10.1107/S160053681204024X

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Triaqua(cyclohex-4-ene-1,2-dicarboxylato-κO¹)(1,10-phenanthroline-κ²N,N′)cobalt(II)

Hai-Ye Li,^a Cheng Wang,^a Fu-Ping Huang ^a and Yi-Min Jiang ^a ^*

^aCollege of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin, Guangxi 541004, People's Republic of China
^*Correspondence e-mail: huangfp2006@163.com

(Received 6 September 2012; accepted 22 September 2012; online 20 October 2012)

In the title compound, [Co(C₈H₈O₄)(C₁₂H₈N₂)(H₂O)₃], the Co^II atom is coordinated by two N atoms from a bidentate 1,10-phenanthroline ligand, one O atom from a monodentate 4-cyclohexene-1,2-dicarboxylate ligand and three water O atoms in a distorted octahedral geometry. The mononuclear molecules are engaged in extensive intra- and intermolecular O—H⋯O hydrogen-bonding interactions and π–π stacking interactions [centroid–centroid distance = 3.784 (3) Å], forming a three-dimensional supramolecular network.

Related literature

For background to compounds with metal-organic framework structures, see: Huang et al. (2010 ); Ockwig et al. (2005 ); Rao et al. (2004 ). For a description of the Cambridge Structural Database (CSD), see: Allen (2002 ). For 4-cyclohexene-1,2-dicarboxylates, see: Kim et al. (2004 ); Lee et al. (2006 ). For related structures, see: Baruah et al. (2007 ); Hou et al. (2007 ); Zhang et al. (2008 ).

Experimental

Crystal data

[Co(C₈H₈O₄)(C₁₂H₈N₂)(H₂O)₃]
M_r = 461.33
Monoclinic, P 2₁ /c
a = 8.1730 (16) Å
b = 20.210 (4) Å
c = 12.068 (2) Å
β = 91.44 (3)°
V = 1992.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 293 K
0.40 × 0.20 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.801, T_max = 0.945
15996 measured reflections
3606 independent reflections
2982 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.122
S = 0.99
3606 reflections
295 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O3ⁱ	0.85 (3)	1.85 (3)	2.695 (4)	171 (4)
O5—H5B⋯O4	0.86 (4)	2.06 (4)	2.912 (4)	172 (4)
O6—H6A⋯O4ⁱ	0.86 (3)	1.86 (4)	2.716 (4)	174 (5)
O6—H6B⋯O3	0.86 (3)	1.99 (3)	2.835 (4)	165 (3)
O7—H7A⋯O2	0.86 (3)	1.77 (4)	2.610 (4)	165 (4)
O7—H7B⋯O4ⁱⁱ	0.86 (3)	1.87 (3)	2.734 (4)	175 (4)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1, y, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681204024X/zq2181sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204024X/zq2181Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681204024X/zq2181Isup3.cdx

checkCIF report

Comment top

Recently, carboxylic acid (as well as carboxylate) has been widely applied in engineering studies of inorganic-organic hybrid materials and the construction of metal-organic coordination supramolecular complexes (Huang et al., 2010; Ockwig et al., 2005; Rao et al., 2004). Although the Cambridge Structural Database (Allen, 2002) contains a great number of transition metal derivatives of carboxylic acids, the metal derivatives of cis-4-cyclohexene-1,2-dicarboxylate acid documented are surprisingly rare (Kim et al., 2004; Lee et al., 2006). As part of this ongoing work, the title complex, [Co(C₈H₈O₄)(C₁₂H₈N₂)(H₂O)₃], has been prepared and structurally characterized (Fig. 1).

In the title compound, the Co^II atom is coordinated by two N atoms from a bidentate 1,10-phenanthroline ligand (phen), one O atom from a monodentate cis-4-cyclohexene-1,2-dicarboxylate ligand, and three O atoms from water molecules in a distorted octahedral geometry. The coordinating Co—N and Co—O bond lengths [Co—N 2.107 (3)–2.122 (3) Å; Co—O 2.071 (3)–2.152 (3) Å] agree well with those observed in analogous complexes (Baruah et al., 2007; Hou et al., 2007; Zhang et al., 2008). The crystal packing (Fig. 2) exhibits intra- and inter-molecular O—H···O hydrogen bonds (Table 1) and π–π stacking interactions [Cg1···Cg2ⁱⁱⁱ distance is 3.784 (3) Å (iii = -x, 1-y, 1-z) between the centroids of the (N1-C9-C10-C11-C12-C20) and (C12-C13-C14-C15-C19-C20) six-membered rings] forming a three-dimensional supramolecular network.

Related literature top

For background to compounds with metal-organic framework structures, see: Huang et al. (2010); Ockwig et al. (2005); Rao et al. (2004). For a description of the Cambridge Structural Database (CSD), see: Allen (2002). For 4-cyclohexene-1,2-dicarboxylates, see: Kim et al. (2004); Lee et al. (2006). For related structures, see: Baruah et al. (2007); Hou et al. (2007); Zhang et al. (2008).

Experimental top

For the preparation of the title complex, cis-4-cyclohexene-1,2-dicarboxylate acid (0.085 g, 0.5 mmol), Co(NO₃)₂.6H₂O (0.12 g, 0.5 mmol), phen (0.10 g, 0.5 mmol) and KHCO₃ (0.10 g, 1 mmol) were dissolved in a water/ethanol solution (20 ml, 1:1). The solution was stirred for 3 h at room temperature and filtered. Red block-shaped crystals were obtained from the filtrate after 4 d.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound with the atom-numbering scheme and displacement ellipsoids at the 30% probability level.
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dotted lines.

Triaqua(cyclohex-4-ene-1,2-dicarboxylato-κO¹)(1,10-phenanthroline- κ²N,N')cobalt(II) top

Crystal data top

[Co(C₈H₈O₄)(C₁₂H₈N₂)(H₂O)₃]	F(000) = 956
M_r = 461.33	D_x = 1.538 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2567 reflections
a = 8.1730 (16) Å	θ = 1.5–25.3°
b = 20.210 (4) Å	µ = 0.91 mm⁻¹
c = 12.068 (2) Å	T = 293 K
β = 91.44 (3)°	Block, red
V = 1992.7 (7) Å³	0.40 × 0.20 × 0.08 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3606 independent reflections
Radiation source: fine-focus sealed tube	2982 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
phi and ω scans	θ_max = 25.3°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.801, T_max = 0.945	k = −24→24
15996 measured reflections	l = −14→14

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0338P)² + 5.P] where P = (F_o² + 2F_c²)/3
3606 reflections	(Δ/σ)_max < 0.001
295 parameters	Δρ_max = 0.28 e Å⁻³
9 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

[Co(C₈H₈O₄)(C₁₂H₈N₂)(H₂O)₃]	V = 1992.7 (7) Å³
M_r = 461.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1730 (16) Å	µ = 0.91 mm⁻¹
b = 20.210 (4) Å	T = 293 K
c = 12.068 (2) Å	0.40 × 0.20 × 0.08 mm
β = 91.44 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3606 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2982 reflections with I > 2σ(I)
T_min = 0.801, T_max = 0.945	R_int = 0.073
15996 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	9 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.28 e Å⁻³
3606 reflections	Δρ_min = −0.34 e Å⁻³
295 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
Co1	0.23393 (6)	0.53534 (3)	0.19466 (4)	0.02844 (17)
C1	0.3182 (5)	0.67605 (19)	0.1389 (3)	0.0319 (9)
C2	0.4497 (5)	0.71600 (19)	0.0814 (3)	0.0327 (9)
H2A	0.4249	0.7143	0.0016	0.039*
C3	0.4475 (6)	0.7890 (2)	0.1160 (4)	0.0463 (12)
H3A	0.5051	0.8151	0.0620	0.056*
H3B	0.3352	0.8045	0.1169	0.056*
C4	0.5250 (6)	0.7988 (2)	0.2267 (5)	0.0567 (14)
H4A	0.5006	0.8372	0.2655	0.068*
C5	0.6267 (6)	0.7561 (3)	0.2732 (4)	0.0545 (14)
H5C	0.6676	0.7657	0.3440	0.065*
C6	0.6815 (5)	0.6932 (2)	0.2206 (4)	0.0400 (11)
H6C	0.6419	0.6560	0.2632	0.048*
H6D	0.8001	0.6916	0.2228	0.048*
C7	0.6202 (5)	0.68620 (19)	0.1002 (3)	0.0319 (9)
H7C	0.6947	0.7123	0.0553	0.038*
C8	0.6262 (5)	0.61588 (19)	0.0556 (3)	0.0305 (9)
C9	0.3023 (5)	0.5544 (2)	0.4478 (3)	0.0387 (10)
H9A	0.3474	0.5952	0.4298	0.046*
C10	0.3035 (6)	0.5346 (2)	0.5592 (4)	0.0460 (12)
H10A	0.3491	0.5619	0.6138	0.055*
C11	0.2385 (6)	0.4760 (2)	0.5869 (4)	0.0446 (12)
H11A	0.2392	0.4628	0.6608	0.054*
C12	0.1695 (5)	0.4345 (2)	0.5047 (3)	0.0369 (10)
C13	0.0959 (6)	0.3723 (2)	0.5252 (4)	0.0446 (11)
H13A	0.0915	0.3568	0.5976	0.054*
C14	0.0322 (6)	0.3351 (2)	0.4419 (4)	0.0457 (12)
H14A	−0.0140	0.2942	0.4577	0.055*
C15	0.0348 (5)	0.3577 (2)	0.3300 (3)	0.0359 (10)
C16	−0.0345 (5)	0.3215 (2)	0.2400 (4)	0.0426 (11)
H16A	−0.0839	0.2807	0.2518	0.051*
C17	−0.0280 (5)	0.3472 (2)	0.1365 (4)	0.0429 (11)
H17A	−0.0732	0.3242	0.0764	0.051*
C18	0.0467 (5)	0.4080 (2)	0.1210 (3)	0.0357 (10)
H18A	0.0505	0.4246	0.0493	0.043*
C19	0.1057 (5)	0.41830 (19)	0.3069 (3)	0.0295 (9)
C20	0.1743 (5)	0.4581 (2)	0.3947 (3)	0.0306 (9)
N1	0.2392 (4)	0.51715 (16)	0.3679 (3)	0.0312 (8)
N2	0.1127 (4)	0.44351 (16)	0.2022 (3)	0.0295 (8)
O1	0.3622 (3)	0.62360 (13)	0.1889 (2)	0.0315 (6)
O2	0.1735 (3)	0.69566 (14)	0.1286 (3)	0.0439 (8)
O3	0.5410 (3)	0.60345 (14)	−0.0292 (2)	0.0382 (7)
O4	0.7164 (3)	0.57339 (13)	0.1038 (2)	0.0356 (7)
O5	0.4681 (4)	0.48671 (15)	0.1938 (2)	0.0349 (7)
O6	0.2453 (4)	0.53756 (15)	0.0198 (2)	0.0334 (7)
O7	0.0207 (4)	0.59085 (15)	0.1985 (3)	0.0378 (7)
H5A	0.465 (6)	0.4552 (16)	0.147 (3)	0.062 (17)*
H6A	0.258 (5)	0.5009 (13)	−0.015 (4)	0.061 (17)*
H7A	0.054 (5)	0.6283 (14)	0.174 (4)	0.052 (15)*
H5B	0.538 (5)	0.5151 (17)	0.172 (4)	0.059 (17)*
H6B	0.324 (4)	0.5630 (16)	0.000 (4)	0.054 (16)*
H7B	−0.077 (3)	0.584 (2)	0.172 (4)	0.059 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0293 (3)	0.0295 (3)	0.0264 (3)	−0.0004 (2)	0.0010 (2)	0.0015 (2)
C1	0.037 (3)	0.025 (2)	0.033 (2)	0.0006 (18)	0.0004 (18)	−0.0067 (18)
C2	0.039 (2)	0.028 (2)	0.031 (2)	0.0023 (18)	0.0014 (18)	0.0018 (18)
C3	0.044 (3)	0.027 (2)	0.069 (3)	0.001 (2)	0.008 (2)	0.004 (2)
C4	0.053 (3)	0.038 (3)	0.080 (4)	0.002 (2)	0.005 (3)	−0.028 (3)
C5	0.055 (3)	0.058 (3)	0.050 (3)	−0.009 (3)	−0.001 (2)	−0.030 (3)
C6	0.039 (3)	0.040 (3)	0.040 (3)	−0.005 (2)	−0.005 (2)	−0.008 (2)
C7	0.031 (2)	0.031 (2)	0.034 (2)	−0.0034 (18)	0.0025 (18)	0.0011 (18)
C8	0.028 (2)	0.030 (2)	0.034 (2)	−0.0042 (18)	0.0074 (18)	−0.0021 (18)
C9	0.045 (3)	0.038 (2)	0.033 (2)	−0.005 (2)	0.000 (2)	−0.0021 (19)
C10	0.059 (3)	0.047 (3)	0.032 (2)	−0.002 (2)	−0.010 (2)	−0.010 (2)
C11	0.057 (3)	0.050 (3)	0.027 (2)	0.002 (2)	−0.003 (2)	0.001 (2)
C12	0.039 (3)	0.042 (3)	0.030 (2)	0.002 (2)	0.0023 (19)	0.0049 (19)
C13	0.054 (3)	0.050 (3)	0.030 (2)	−0.004 (2)	−0.001 (2)	0.011 (2)
C14	0.054 (3)	0.043 (3)	0.040 (3)	−0.009 (2)	0.002 (2)	0.011 (2)
C15	0.035 (2)	0.038 (2)	0.035 (2)	−0.0007 (19)	−0.0006 (19)	0.0013 (19)
C16	0.040 (3)	0.037 (3)	0.051 (3)	−0.011 (2)	−0.001 (2)	0.002 (2)
C17	0.043 (3)	0.049 (3)	0.036 (3)	−0.012 (2)	−0.005 (2)	−0.004 (2)
C18	0.038 (2)	0.043 (3)	0.026 (2)	−0.003 (2)	−0.0022 (18)	−0.0007 (19)
C19	0.027 (2)	0.033 (2)	0.028 (2)	−0.0013 (17)	0.0009 (17)	0.0007 (17)
C20	0.030 (2)	0.035 (2)	0.026 (2)	0.0045 (18)	0.0017 (17)	0.0014 (18)
N1	0.033 (2)	0.0333 (19)	0.0272 (19)	0.0009 (15)	0.0018 (15)	−0.0008 (15)
N2	0.0291 (18)	0.0335 (19)	0.0261 (18)	−0.0026 (15)	0.0024 (14)	−0.0007 (14)
O1	0.0310 (15)	0.0284 (15)	0.0349 (16)	−0.0012 (12)	−0.0008 (12)	0.0018 (12)
O2	0.0292 (17)	0.0342 (17)	0.068 (2)	0.0063 (13)	−0.0034 (15)	0.0008 (15)
O3	0.0409 (17)	0.0386 (17)	0.0349 (17)	0.0004 (13)	−0.0023 (14)	−0.0103 (13)
O4	0.0337 (16)	0.0298 (16)	0.0432 (18)	0.0029 (13)	−0.0031 (13)	−0.0023 (13)
O5	0.0360 (18)	0.0356 (17)	0.0329 (17)	0.0033 (14)	0.0010 (13)	−0.0023 (14)
O6	0.0376 (18)	0.0334 (17)	0.0293 (16)	−0.0010 (14)	0.0023 (12)	−0.0015 (14)
O7	0.0280 (17)	0.0381 (19)	0.0474 (19)	0.0029 (14)	0.0000 (14)	0.0003 (15)

Geometric parameters (Å, º) top

Co1—O1	2.071 (3)	C9—H9A	0.9300
Co1—O7	2.074 (3)	C10—C11	1.345 (6)
Co1—N2	2.107 (3)	C10—H10A	0.9300
Co1—O6	2.115 (3)	C11—C12	1.407 (6)
Co1—N1	2.122 (3)	C11—H11A	0.9300
Co1—O5	2.152 (3)	C12—C20	1.412 (5)
C1—O2	1.250 (5)	C12—C13	1.418 (6)
C1—O1	1.268 (5)	C13—C14	1.348 (6)
C1—C2	1.525 (6)	C13—H13A	0.9300
C2—C7	1.530 (6)	C14—C15	1.427 (6)
C2—C3	1.533 (6)	C14—H14A	0.9300
C2—H2A	0.9800	C15—C19	1.387 (6)
C3—C4	1.477 (7)	C15—C16	1.415 (6)
C3—H3A	0.9700	C16—C17	1.355 (6)
C3—H3B	0.9700	C16—H16A	0.9300
C4—C5	1.315 (7)	C17—C18	1.386 (6)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.494 (6)	C18—N2	1.319 (5)
C5—H5C	0.9300	C18—H18A	0.9300
C6—C7	1.531 (6)	C19—N2	1.364 (5)
C6—H6C	0.9700	C19—C20	1.433 (5)
C6—H6D	0.9700	C20—N1	1.349 (5)
C7—C8	1.521 (5)	O5—H5A	0.852 (19)
C7—H7C	0.9800	O5—H5B	0.854 (19)
C8—O3	1.250 (5)	O6—H6A	0.860 (19)
C8—O4	1.264 (5)	O6—H6B	0.859 (19)
C9—N1	1.319 (5)	O7—H7A	0.859 (18)
C9—C10	1.403 (6)	O7—H7B	0.858 (19)

O1—Co1—O7	87.78 (12)	N1—C9—H9A	119.0
O1—Co1—N2	177.61 (12)	C10—C9—H9A	119.0
O7—Co1—N2	94.53 (13)	C11—C10—C9	119.8 (4)
O1—Co1—O6	85.03 (11)	C11—C10—H10A	120.1
O7—Co1—O6	93.97 (12)	C9—C10—H10A	120.1
N2—Co1—O6	95.43 (12)	C10—C11—C12	120.3 (4)
O1—Co1—N1	100.63 (12)	C10—C11—H11A	119.9
O7—Co1—N1	93.88 (12)	C12—C11—H11A	119.9
N2—Co1—N1	78.61 (12)	C11—C12—C20	116.2 (4)
O6—Co1—N1	170.49 (12)	C11—C12—C13	124.7 (4)
O1—Co1—O5	86.69 (11)	C20—C12—C13	119.0 (4)
O7—Co1—O5	174.34 (13)	C14—C13—C12	121.4 (4)
N2—Co1—O5	90.99 (12)	C14—C13—H13A	119.3
O6—Co1—O5	86.76 (11)	C12—C13—H13A	119.3
N1—Co1—O5	85.96 (12)	C13—C14—C15	120.9 (4)
O2—C1—O1	124.7 (4)	C13—C14—H14A	119.6
O2—C1—C2	117.6 (4)	C15—C14—H14A	119.6
O1—C1—C2	117.7 (4)	C19—C15—C16	117.6 (4)
C1—C2—C7	112.0 (3)	C19—C15—C14	119.3 (4)
C1—C2—C3	111.9 (3)	C16—C15—C14	123.1 (4)
C7—C2—C3	110.8 (3)	C17—C16—C15	119.0 (4)
C1—C2—H2A	107.3	C17—C16—H16A	120.5
C7—C2—H2A	107.3	C15—C16—H16A	120.5
C3—C2—H2A	107.3	C16—C17—C18	119.4 (4)
C4—C3—C2	111.6 (4)	C16—C17—H17A	120.3
C4—C3—H3A	109.3	C18—C17—H17A	120.3
C2—C3—H3A	109.3	N2—C18—C17	123.8 (4)
C4—C3—H3B	109.3	N2—C18—H18A	118.1
C2—C3—H3B	109.3	C17—C18—H18A	118.1
H3A—C3—H3B	108.0	N2—C19—C15	122.9 (4)
C5—C4—C3	123.3 (4)	N2—C19—C20	116.8 (3)
C5—C4—H4A	118.3	C15—C19—C20	120.3 (4)
C3—C4—H4A	118.3	N1—C20—C12	123.0 (4)
C4—C5—C6	124.8 (5)	N1—C20—C19	117.9 (3)
C4—C5—H5C	117.6	C12—C20—C19	119.1 (4)
C6—C5—H5C	117.6	C9—N1—C20	118.6 (3)
C5—C6—C7	112.8 (4)	C9—N1—Co1	128.3 (3)
C5—C6—H6C	109.0	C20—N1—Co1	113.0 (3)
C7—C6—H6C	109.0	C18—N2—C19	117.3 (3)
C5—C6—H6D	109.0	C18—N2—Co1	129.1 (3)
C7—C6—H6D	109.0	C19—N2—Co1	113.6 (2)
H6C—C6—H6D	107.8	C1—O1—Co1	126.8 (2)
C8—C7—C2	110.7 (3)	Co1—O5—H5A	109 (3)
C8—C7—C6	114.2 (3)	Co1—O5—H5B	107 (3)
C2—C7—C6	112.3 (3)	H5A—O5—H5B	108 (3)
C8—C7—H7C	106.4	Co1—O6—H6A	119 (3)
C2—C7—H7C	106.4	Co1—O6—H6B	110 (3)
C6—C7—H7C	106.4	H6A—O6—H6B	107 (3)
O3—C8—O4	123.2 (4)	Co1—O7—H7A	101 (3)
O3—C8—C7	117.1 (4)	Co1—O7—H7B	133 (3)
O4—C8—C7	119.7 (4)	H7A—O7—H7B	108 (3)
N1—C9—C10	122.1 (4)

O2—C1—C2—C7	−179.6 (3)	N2—C19—C20—N1	0.4 (5)
O1—C1—C2—C7	−3.0 (5)	C15—C19—C20—N1	−178.9 (4)
O2—C1—C2—C3	55.3 (5)	N2—C19—C20—C12	179.7 (3)
O1—C1—C2—C3	−128.1 (4)	C15—C19—C20—C12	0.4 (6)
C1—C2—C3—C4	77.6 (5)	C10—C9—N1—C20	−0.1 (6)
C7—C2—C3—C4	−48.1 (5)	C10—C9—N1—Co1	−177.0 (3)
C2—C3—C4—C5	20.1 (7)	C12—C20—N1—C9	0.5 (6)
C3—C4—C5—C6	1.7 (9)	C19—C20—N1—C9	179.7 (4)
C4—C5—C6—C7	5.8 (7)	C12—C20—N1—Co1	177.9 (3)
C1—C2—C7—C8	59.8 (4)	C19—C20—N1—Co1	−2.9 (4)
C3—C2—C7—C8	−174.5 (3)	O1—Co1—N1—C9	2.4 (4)
C1—C2—C7—C6	−69.1 (4)	O7—Co1—N1—C9	−86.0 (4)
C3—C2—C7—C6	56.6 (5)	N2—Co1—N1—C9	−179.9 (4)
C5—C6—C7—C8	−161.8 (4)	O5—Co1—N1—C9	88.3 (4)
C5—C6—C7—C2	−34.8 (5)	O1—Co1—N1—C20	−174.6 (3)
C2—C7—C8—O3	34.0 (5)	O7—Co1—N1—C20	96.9 (3)
C6—C7—C8—O3	161.9 (4)	N2—Co1—N1—C20	3.1 (3)
C2—C7—C8—O4	−146.7 (4)	O5—Co1—N1—C20	−88.7 (3)
C6—C7—C8—O4	−18.9 (5)	C17—C18—N2—C19	−0.1 (6)
N1—C9—C10—C11	−0.2 (7)	C17—C18—N2—Co1	178.9 (3)
C9—C10—C11—C12	0.1 (7)	C15—C19—N2—C18	0.7 (6)
C10—C11—C12—C20	0.3 (7)	C20—C19—N2—C18	−178.6 (4)
C10—C11—C12—C13	−179.0 (5)	C15—C19—N2—Co1	−178.4 (3)
C11—C12—C13—C14	−180.0 (5)	C20—C19—N2—Co1	2.3 (4)
C20—C12—C13—C14	0.7 (7)	O7—Co1—N2—C18	85.1 (4)
C12—C13—C14—C15	−0.8 (7)	O6—Co1—N2—C18	−9.4 (4)
C13—C14—C15—C19	0.7 (7)	N1—Co1—N2—C18	178.1 (4)
C13—C14—C15—C16	−178.1 (4)	O5—Co1—N2—C18	−96.2 (4)
C19—C15—C16—C17	0.4 (6)	O1—Co1—N2—C19	69 (3)
C14—C15—C16—C17	179.2 (4)	O7—Co1—N2—C19	−95.9 (3)
C15—C16—C17—C18	0.2 (7)	O6—Co1—N2—C19	169.6 (3)
C16—C17—C18—N2	−0.4 (7)	N1—Co1—N2—C19	−2.9 (3)
C16—C15—C19—N2	−0.9 (6)	O5—Co1—N2—C19	82.8 (3)
C14—C15—C19—N2	−179.8 (4)	O2—C1—O1—Co1	34.6 (6)
C16—C15—C19—C20	178.4 (4)	C2—C1—O1—Co1	−141.7 (3)
C14—C15—C19—C20	−0.5 (6)	O7—Co1—O1—C1	−36.1 (3)
C11—C12—C20—N1	−0.6 (6)	O6—Co1—O1—C1	58.1 (3)
C13—C12—C20—N1	178.8 (4)	N1—Co1—O1—C1	−129.6 (3)
C11—C12—C20—C19	−179.8 (4)	O5—Co1—O1—C1	145.1 (3)
C13—C12—C20—C19	−0.4 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3ⁱ	0.85 (3)	1.85 (3)	2.695 (4)	171 (4)
O5—H5B···O4	0.86 (4)	2.06 (4)	2.912 (4)	172 (4)
O6—H6A···O4ⁱ	0.86 (3)	1.86 (4)	2.716 (4)	174 (5)
O6—H6B···O3	0.86 (3)	1.99 (3)	2.835 (4)	165 (3)
O7—H7A···O2	0.86 (3)	1.77 (4)	2.610 (4)	165 (4)
O7—H7B···O4ⁱⁱ	0.86 (3)	1.87 (3)	2.734 (4)	175 (4)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Co(C₈H₈O₄)(C₁₂H₈N₂)(H₂O)₃]
M_r	461.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.1730 (16), 20.210 (4), 12.068 (2)
β (°)	91.44 (3)
V (Å³)	1992.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.40 × 0.20 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.801, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	15996, 3606, 2982
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.122, 0.99
No. of reflections	3606
No. of parameters	295
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.34

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3ⁱ	0.85 (3)	1.85 (3)	2.695 (4)	171 (4)
O5—H5B···O4	0.86 (4)	2.06 (4)	2.912 (4)	172 (4)
O6—H6A···O4ⁱ	0.86 (3)	1.86 (4)	2.716 (4)	174 (5)
O6—H6B···O3	0.86 (3)	1.99 (3)	2.835 (4)	165 (3)
O7—H7A···O2	0.86 (3)	1.77 (4)	2.610 (4)	165 (4)
O7—H7B···O4ⁱⁱ	0.86 (3)	1.87 (3)	2.734 (4)	175 (4)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y, z.

Acknowledgements

We gratefully acknowledge the Guangxi Natural Science Foundation of China (2010GXNSFD013017, 2012GXNSFBA053017) and the Natural Science Foundation of Guangxi Normal University.

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