catena-Poly[[diaqua­bis­[2-(3-oxo-1,3-di­hydro-2-benzofuran-1-yl)acetato-κO]cobalt(II)]-μ-1,2-bis­(pyridin-4-yl)ethane-κ2N:N′]

Sun, C.; Li, Y.; Li, W.; Dong, B.

doi:10.1107/S1600536812044339

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page m1433

doi:10.1107/S1600536812044339

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catena-Poly[[diaquabis[2-(3-oxo-1,3-dihydro-2-benzofuran-1-yl)acetato-κO]cobalt(II)]-μ-1,2-bis(pyridin-4-yl)ethane-κ²N:N′]

Changyan Sun,^a ^* Yang Li,^a Wenjun Li ^a and Bin Dong ^a

^aSchool of Chemistry and Biological Engineering, University of Science and Technology Beijing, Beijing 100083, People's Republic of China
^*Correspondence e-mail: cysun@ustb.edu.cn

(Received 17 October 2012; accepted 25 October 2012; online 31 October 2012)

In the title complex, [Co(C₁₀H₇O₄)₂(C₁₂H₁₂N₂)(H₂O)₂]_n, the Co^II ion is located on a crystallographic centre of symmetry and is six-coordinated by two N atoms from two 1,2-bis(4-pyridyl)ethane ligands, two carboxylate O atoms from two 1,3-dihydro-3-oxo-1-isobenzofuranacetate ligands and two terminal water ligands. The 1,2-bis(4-pyridyl)ethane ligands act as bidentate ligands, and bridge the Co^II ions into infinite chains extending parallel to [010]. In these chains, there are intra-molecular O—H⋯O hydrogen bonding between the coordination water molecules and carboxylate groups. Inter-molecular O—H⋯O hydrogen bonding between the adjacent chains and π⋯π stacking interactions result in the formation of a three-dimensional supramolecular network.

Related literature

For in situ ligand reactions, see: Zhang et al. (2005 ); Chen et al. (2007 ); Zhao et al. (2008 ).

Experimental

Crystal data

[Co(C₁₀H₇O₄)₂(C₁₂H₁₂N₂)(H₂O)₂]
M_r = 661.51
Triclinic, $[P \overline 1]$
a = 5.4599 (12) Å
b = 10.374 (2) Å
c = 13.617 (3) Å
α = 93.912 (4)°
β = 99.409 (4)°
γ = 97.651 (4)°
V = 750.9 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.63 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.749, T_max = 1.000
4258 measured reflections
3027 independent reflections
2306 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.133
S = 1.05
3027 reflections
213 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯O2	0.90 (5)	1.72 (5)	2.603 (4)	168 (4)
O5—H5B⋯O1	0.90 (5)	2.57 (4)	2.981 (3)	109 (3)
O5—H5A⋯O1ⁱ	0.76 (4)	1.99 (4)	2.752 (3)	172 (4)
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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/S1600536812044339/hg5263sup1.cif

Supporting information file. DOI: 10.1107/S1600536812044339/hg5263Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044339/hg5263Isup3.hkl

checkCIF report

Comment top

In situ ligand reactions have been extensively used to construct new organic ligands and coordination polymers, with novel structures and potential applications, especially those that could not be obtained in direct preparation from the ligands. Furthermore, they are helpful to study reaction mechanism (Zhang et al., 2005; Chen et al., 2007; Zhao et al., 2008). Herein we report the synthesis and structure of the title complex from in situ hydroxylation and esterification of ethylene group. In the title complex (Fig. 1), each Co^II ion is located on a crystallographic centre of symmetry and coordinated to four oxygen atoms and two nitrogen atoms, and the coordination geometry can be described as a distorted octahedron. 1,3-Dihydro-3-oxo-1 -isobenzofuranacetate ligand adopts a monodentate mode, coordinating to Co^II ion with a carboxylate oxygen atom. While 1,2-bis(4-pyridyl)ethane ligands bridge Co^II ions into one-dimensional infinite chains. In these chains, intra-molecular O—H···O hydrogen bonding are observed between the carboxylate oxygen atoms and the coordination water molecules (O(2)···O(5) 2.603 (4) Å and O(1)···O(5) 2.981 (3) Å). Between the adjacent chains, there are inter-molecular O—H···O hydrogen bonding (O(1)···O(5) 2.752 (3) Å), which connects the chains into a three-dimensional supramolecular network (Table 1 and Fig. 2). 1,3-Dihydro-3-oxo-1-isobenzofuranacetate ligands are parallel and the face-to-face distance is 3.88 Å, indicating the existence of the weak π···π stacking interactions, which brings further stability for the structure.

Related literature top

For in situ ligand reactions, see: Zhang et al. (2005); Chen et al. (2007); Zhao et al. (2008).

Experimental top

A mixture of o-carboxycinnamic acid (0.02 g, 0.1 mmol), CoCl₂.6H₂O (0.024 g, 0.1 mmol), 1,2-bis(4-pyridyl)ethane (0.018 g, 0.1 mmol), and deionized water(5 ml) was sealed in a Teflon-lined stainless vessel(25 ml), and heated at 120 °C for 72 h, then cooled slowly to room temperature. There was no solid obtained. The filtration was left to stand in air. After two weeks, red block single crystals were obtained. Yield: 0.015 g (22.7%).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 coordination environment of Co^II ion in the title complex (the symmetry code for A: -x + 1, -y + 1, -z + 1).
	Fig. 2. The three-dimensional supramolecular network of the title complex (viewed along the a axis).

catena-Poly[[diaquabis[2-(3-oxo-1,3-dihydro-2-benzofuran-1-yl)acetato- κO]cobalt(II)]-µ-1,2-bis(pyridin-4-yl)ethane-κ²N:N'] top

Crystal data top

[Co(C₁₀H₇O₄)₂(C₁₂H₁₂N₂)(H₂O)₂]	Z = 1
M_r = 661.51	F(000) = 343
Triclinic, P1	D_x = 1.463 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.4599 (12) Å	Cell parameters from 1338 reflections
b = 10.374 (2) Å	θ = 1.5–26.4°
c = 13.617 (3) Å	µ = 0.63 mm⁻¹
α = 93.912 (4)°	T = 293 K
β = 99.409 (4)°	Block, red
γ = 97.651 (4)°	0.20 × 0.18 × 0.10 mm
V = 750.9 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3027 independent reflections
Radiation source: fine-focus sealed tube	2306 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
phi and ω scans	θ_max = 26.4°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −4→6
T_min = 0.749, T_max = 1.000	k = −12→12
4258 measured reflections	l = −16→17

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.051P)² + 0.6286P] where P = (F_o² + 2F_c²)/3
3027 reflections	(Δ/σ)_max < 0.001
213 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Co(C₁₀H₇O₄)₂(C₁₂H₁₂N₂)(H₂O)₂]	γ = 97.651 (4)°
M_r = 661.51	V = 750.9 (3) Å³
Triclinic, P1	Z = 1
a = 5.4599 (12) Å	Mo Kα radiation
b = 10.374 (2) Å	µ = 0.63 mm⁻¹
c = 13.617 (3) Å	T = 293 K
α = 93.912 (4)°	0.20 × 0.18 × 0.10 mm
β = 99.409 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3027 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2306 reflections with I > 2σ(I)
T_min = 0.749, T_max = 1.000	R_int = 0.026
4258 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.73 e Å⁻³
3027 reflections	Δρ_min = −0.61 e Å⁻³
213 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	0.5000	0.5000	0.5000	0.0231 (2)
N1	0.5225 (5)	0.4729 (3)	0.34064 (18)	0.0312 (7)
O1	0.6967 (4)	0.3420 (2)	0.52914 (16)	0.0326 (6)
O2	0.3880 (5)	0.1819 (3)	0.5357 (3)	0.0613 (9)
O3	0.7376 (7)	0.1884 (4)	0.7644 (2)	0.0817 (12)
O4	0.9063 (9)	0.2427 (5)	0.9246 (3)	0.1123 (17)
C1	0.6125 (7)	0.2293 (4)	0.5499 (3)	0.0358 (9)
C2	0.8056 (8)	0.1465 (4)	0.5951 (3)	0.0498 (11)
H2A	0.8187	0.0778	0.5451	0.060*
H2B	0.9680	0.2009	0.6124	0.060*
C3	0.7443 (8)	0.0860 (5)	0.6858 (3)	0.0566 (12)
H3	0.5815	0.0296	0.6696	0.068*
C4	0.9426 (8)	0.0100 (5)	0.7330 (3)	0.0523 (11)
C5	1.0204 (9)	0.0604 (5)	0.8312 (3)	0.0574 (12)
C6	1.1928 (11)	0.0029 (6)	0.8936 (4)	0.0823 (17)
H6	1.2403	0.0335	0.9607	0.099*
C7	1.2914 (11)	−0.0991 (6)	0.8550 (4)	0.0839 (18)
H7	1.4078	−0.1382	0.8961	0.101*
C8	1.2209 (10)	−0.1446 (5)	0.7563 (4)	0.0710 (15)
H8	1.2932	−0.2131	0.7311	0.085*
C9	1.0467 (9)	−0.0916 (5)	0.6938 (4)	0.0640 (13)
H9	0.9998	−0.1231	0.6268	0.077*
C10	0.8928 (11)	0.1723 (6)	0.8499 (4)	0.0753 (16)
C11	0.7230 (7)	0.5193 (4)	0.3025 (3)	0.0454 (10)
H11	0.8650	0.5601	0.3464	0.054*
C12	0.7320 (8)	0.5102 (5)	0.2011 (3)	0.0532 (11)
H12	0.8763	0.5454	0.1787	0.064*
C13	0.5273 (8)	0.4491 (4)	0.1340 (2)	0.0453 (10)
C14	0.3274 (8)	0.3949 (5)	0.1727 (3)	0.0607 (13)
H14	0.1884	0.3480	0.1305	0.073*
C15	0.3302 (8)	0.4094 (5)	0.2746 (3)	0.0542 (12)
H15	0.1892	0.3725	0.2984	0.065*
C16	0.5295 (10)	0.4387 (5)	0.0226 (3)	0.0609 (13)
H16A	0.6935	0.4220	0.0109	0.073*
H16B	0.4068	0.3655	−0.0098	0.073*
O5	0.1581 (5)	0.3715 (3)	0.47022 (17)	0.0317 (6)
H5A	0.026 (8)	0.368 (4)	0.482 (3)	0.049 (13)*
H5B	0.216 (8)	0.299 (5)	0.491 (3)	0.057 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0194 (3)	0.0328 (4)	0.0189 (3)	0.0042 (3)	0.0066 (2)	0.0067 (3)
N1	0.0312 (15)	0.045 (2)	0.0198 (13)	0.0076 (13)	0.0064 (11)	0.0088 (13)
O1	0.0244 (12)	0.0404 (17)	0.0372 (13)	0.0099 (11)	0.0096 (10)	0.0136 (11)
O2	0.0341 (16)	0.046 (2)	0.108 (3)	0.0054 (13)	0.0149 (16)	0.0305 (18)
O3	0.104 (3)	0.095 (3)	0.064 (2)	0.061 (2)	0.026 (2)	0.017 (2)
O4	0.165 (4)	0.123 (4)	0.063 (2)	0.060 (3)	0.036 (3)	−0.007 (2)
C1	0.033 (2)	0.042 (2)	0.0386 (19)	0.0136 (17)	0.0135 (15)	0.0137 (17)
C2	0.049 (2)	0.052 (3)	0.057 (2)	0.021 (2)	0.0152 (19)	0.024 (2)
C3	0.051 (3)	0.056 (3)	0.066 (3)	0.008 (2)	0.010 (2)	0.026 (2)
C4	0.056 (3)	0.050 (3)	0.051 (2)	0.012 (2)	0.002 (2)	0.017 (2)
C5	0.063 (3)	0.060 (3)	0.050 (2)	0.012 (2)	0.007 (2)	0.015 (2)
C6	0.100 (4)	0.089 (5)	0.052 (3)	0.021 (4)	−0.016 (3)	0.019 (3)
C7	0.092 (4)	0.073 (4)	0.083 (4)	0.033 (3)	−0.022 (3)	0.025 (3)
C8	0.073 (3)	0.050 (3)	0.088 (4)	0.022 (3)	−0.006 (3)	0.015 (3)
C9	0.082 (3)	0.045 (3)	0.062 (3)	0.022 (3)	−0.009 (2)	0.003 (2)
C10	0.098 (4)	0.083 (4)	0.056 (3)	0.036 (3)	0.023 (3)	0.016 (3)
C11	0.047 (2)	0.059 (3)	0.0278 (18)	−0.0039 (19)	0.0091 (16)	0.0049 (18)
C12	0.061 (3)	0.067 (3)	0.035 (2)	0.001 (2)	0.023 (2)	0.010 (2)
C13	0.069 (3)	0.052 (3)	0.0201 (17)	0.019 (2)	0.0123 (18)	0.0091 (17)
C14	0.053 (3)	0.097 (4)	0.0250 (19)	0.000 (2)	−0.0016 (18)	−0.007 (2)
C15	0.043 (2)	0.088 (4)	0.0270 (18)	−0.009 (2)	0.0090 (17)	0.002 (2)
C16	0.095 (4)	0.071 (4)	0.0237 (19)	0.033 (3)	0.014 (2)	0.0065 (19)
O5	0.0219 (13)	0.0407 (17)	0.0342 (13)	0.0022 (11)	0.0096 (10)	0.0082 (11)

Geometric parameters (Å, º) top

Co1—O1	2.101 (2)	C5—C10	1.461 (7)
Co1—O1ⁱ	2.101 (2)	C6—C7	1.362 (7)
Co1—O5ⁱ	2.108 (3)	C6—H6	0.9300
Co1—O5	2.108 (3)	C7—C8	1.369 (7)
Co1—N1ⁱ	2.195 (2)	C7—H7	0.9300
Co1—N1	2.195 (2)	C8—C9	1.368 (6)
N1—C15	1.331 (5)	C8—H8	0.9300
N1—C11	1.334 (5)	C9—H9	0.9300
O1—C1	1.266 (4)	C11—C12	1.386 (5)
O2—C1	1.238 (4)	C11—H11	0.9300
O3—C10	1.357 (6)	C12—C13	1.373 (6)
O3—C3	1.464 (6)	C12—H12	0.9300
O4—C10	1.197 (6)	C13—C14	1.360 (6)
C1—C2	1.526 (5)	C13—C16	1.515 (5)
C2—C3	1.488 (5)	C14—C15	1.383 (5)
C2—H2A	0.9700	C14—H14	0.9300
C2—H2B	0.9700	C15—H15	0.9300
C3—C4	1.509 (6)	C16—C16ⁱⁱ	1.501 (9)
C3—H3	0.9800	C16—H16A	0.9700
C4—C9	1.379 (6)	C16—H16B	0.9700
C4—C5	1.379 (6)	O5—H5A	0.76 (4)
C5—C6	1.386 (6)	O5—H5B	0.90 (5)

O1—Co1—O1ⁱ	180.000 (1)	C6—C5—C10	131.1 (5)
O1—Co1—O5ⁱ	89.80 (10)	C7—C6—C5	118.9 (5)
O1ⁱ—Co1—O5ⁱ	90.20 (10)	C7—C6—H6	120.5
O1—Co1—O5	90.20 (10)	C5—C6—H6	120.5
O1ⁱ—Co1—O5	89.80 (10)	C6—C7—C8	120.6 (4)
O5ⁱ—Co1—O5	180.00 (14)	C6—C7—H7	119.7
O1—Co1—N1ⁱ	89.22 (9)	C8—C7—H7	119.7
O1ⁱ—Co1—N1ⁱ	90.78 (9)	C9—C8—C7	121.6 (5)
O5ⁱ—Co1—N1ⁱ	88.53 (10)	C9—C8—H8	119.2
O5—Co1—N1ⁱ	91.47 (10)	C7—C8—H8	119.2
O1—Co1—N1	90.78 (9)	C8—C9—C4	118.0 (4)
O1ⁱ—Co1—N1	89.22 (9)	C8—C9—H9	121.0
O5ⁱ—Co1—N1	91.47 (10)	C4—C9—H9	121.0
O5—Co1—N1	88.53 (10)	O4—C10—O3	121.3 (5)
N1ⁱ—Co1—N1	180.000 (1)	O4—C10—C5	130.3 (5)
C15—N1—C11	115.3 (3)	O3—C10—C5	108.4 (4)
C15—N1—Co1	121.1 (2)	N1—C11—C12	123.8 (4)
C11—N1—Co1	123.6 (2)	N1—C11—H11	118.1
C1—O1—Co1	128.2 (2)	C12—C11—H11	118.1
C10—O3—C3	110.7 (4)	C13—C12—C11	119.8 (4)
O2—C1—O1	125.1 (3)	C13—C12—H12	120.1
O2—C1—C2	118.2 (4)	C11—C12—H12	120.1
O1—C1—C2	116.7 (3)	C14—C13—C12	116.7 (3)
C3—C2—C1	113.8 (3)	C14—C13—C16	122.0 (4)
C3—C2—H2A	108.8	C12—C13—C16	121.3 (4)
C1—C2—H2A	108.8	C13—C14—C15	120.3 (4)
C3—C2—H2B	108.8	C13—C14—H14	119.9
C1—C2—H2B	108.8	C15—C14—H14	119.9
H2A—C2—H2B	107.7	N1—C15—C14	124.0 (4)
O3—C3—C2	109.7 (4)	N1—C15—H15	118.0
O3—C3—C4	103.6 (3)	C14—C15—H15	118.0
C2—C3—C4	113.4 (4)	C16ⁱⁱ—C16—C13	111.5 (4)
O3—C3—H3	110.0	C16ⁱⁱ—C16—H16A	109.3
C2—C3—H3	110.0	C13—C16—H16A	109.3
C4—C3—H3	110.0	C16ⁱⁱ—C16—H16B	109.3
C9—C4—C5	120.9 (4)	C13—C16—H16B	109.3
C9—C4—C3	131.1 (4)	H16A—C16—H16B	108.0
C5—C4—C3	108.0 (4)	Co1—O5—H5A	138 (3)
C4—C5—C6	119.9 (5)	Co1—O5—H5B	99 (3)
C4—C5—C10	109.0 (4)	H5A—O5—H5B	106 (4)

O1—Co1—N1—C15	99.1 (3)	C3—C4—C5—C10	−3.4 (6)
O1ⁱ—Co1—N1—C15	−80.9 (3)	C4—C5—C6—C7	3.1 (9)
O5ⁱ—Co1—N1—C15	−171.1 (3)	C10—C5—C6—C7	−177.3 (6)
O5—Co1—N1—C15	8.9 (3)	C5—C6—C7—C8	−0.2 (10)
O1—Co1—N1—C11	−82.1 (3)	C6—C7—C8—C9	−1.4 (10)
O1ⁱ—Co1—N1—C11	97.9 (3)	C7—C8—C9—C4	0.0 (8)
O5ⁱ—Co1—N1—C11	7.7 (3)	C5—C4—C9—C8	2.9 (8)
O5—Co1—N1—C11	−172.3 (3)	C3—C4—C9—C8	−178.1 (5)
O5ⁱ—Co1—O1—C1	161.1 (3)	C3—O3—C10—O4	−176.7 (6)
O5—Co1—O1—C1	−18.9 (3)	C3—O3—C10—C5	2.4 (6)
N1ⁱ—Co1—O1—C1	72.6 (3)	C4—C5—C10—O4	179.7 (7)
N1—Co1—O1—C1	−107.4 (3)	C6—C5—C10—O4	0.1 (11)
Co1—O1—C1—O2	16.8 (5)	C4—C5—C10—O3	0.7 (6)
Co1—O1—C1—C2	−163.8 (2)	C6—C5—C10—O3	−178.9 (5)
O2—C1—C2—C3	−48.9 (6)	C15—N1—C11—C12	3.5 (6)
O1—C1—C2—C3	131.7 (4)	Co1—N1—C11—C12	−175.4 (3)
C10—O3—C3—C2	−125.7 (4)	N1—C11—C12—C13	−0.9 (7)
C10—O3—C3—C4	−4.3 (5)	C11—C12—C13—C14	−2.9 (7)
C1—C2—C3—O3	−61.7 (5)	C11—C12—C13—C16	179.3 (4)
C1—C2—C3—C4	−177.1 (4)	C12—C13—C14—C15	3.8 (7)
O3—C3—C4—C9	−174.5 (5)	C16—C13—C14—C15	−178.4 (4)
C2—C3—C4—C9	−55.6 (7)	C11—N1—C15—C14	−2.5 (7)
O3—C3—C4—C5	4.6 (5)	Co1—N1—C15—C14	176.4 (4)
C2—C3—C4—C5	123.5 (5)	C13—C14—C15—N1	−1.2 (8)
C9—C4—C5—C6	−4.5 (8)	C14—C13—C16—C16ⁱⁱ	100.1 (7)
C3—C4—C5—C6	176.3 (5)	C12—C13—C16—C16ⁱⁱ	−82.3 (7)
C9—C4—C5—C10	175.8 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O2	0.90 (5)	1.72 (5)	2.603 (4)	168 (4)
O5—H5B···O1	0.90 (5)	2.57 (4)	2.981 (3)	109 (3)
O5—H5A···O1ⁱⁱⁱ	0.76 (4)	1.99 (4)	2.752 (3)	172 (4)

Symmetry code: (iii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Co(C₁₀H₇O₄)₂(C₁₂H₁₂N₂)(H₂O)₂]
M_r	661.51
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.4599 (12), 10.374 (2), 13.617 (3)
α, β, γ (°)	93.912 (4), 99.409 (4), 97.651 (4)
V (Å³)	750.9 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.749, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4258, 3027, 2306
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.133, 1.05
No. of reflections	3027
No. of parameters	213
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.61

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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—H5B···O2	0.90 (5)	1.72 (5)	2.603 (4)	168 (4)
O5—H5B···O1	0.90 (5)	2.57 (4)	2.981 (3)	109 (3)
O5—H5A···O1ⁱ	0.76 (4)	1.99 (4)	2.752 (3)	172 (4)

Symmetry code: (i) x−1, y, z.

Acknowledgements

This work was supported by National Nature Science Foundation of China (No. 21101013) and Fundamental Research Funds for the Central Universities (No. FRF-BR-10–002 A).

References

Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Zhang, X. M. (2005). Coord. Chem. Rev. 249, 1201–1219. Web of Science CrossRef CAS Google Scholar
Zhao, H., Qu, Z. R., Ye, H. Y. & Xiong, R. G. (2008). Chem. Soc. Rev. 37, 84–100. Web of Science CrossRef PubMed Google Scholar

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