Poly[[diaqua­(μ-4,4′-bipyridine N,N′-di­oxide-κ2O:O′)(μ-terephthalato-κ2O1:O4)cobalt(II)] 4,4′-bipyridine N,N′-dioxide monosolvate]

Ge, X.; Song, S.-Y.

doi:10.1107/S1600536812040056

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page m1307

https://doi.org/10.1107/S1600536812040056

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Poly[[diaqua(μ-4,4′-bipyridine N,N′-dioxide-κ²O:O′)(μ-terephthalato-κ²O¹:O⁴)cobalt(II)] 4,4′-bipyridine N,N′-dioxide monosolvate]

Xin Ge ^a and Shu-Yan Song ^a ^*

^aState Key Laboratory of Rare Earth Resource Utilization, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, People's Republic of China
^*Correspondence e-mail: songsy@ciac.jl.cn

(Received 16 September 2012; accepted 21 September 2012; online 26 September 2012)

In the title compound, {[Co(C₈H₄O₄)(C₁₀H₈N₂O₂)(H₂O)₂]·C₁₀H₈N₂O₂}_n, the Co^II atom, lying on an inversion center, is hexacoordinated in a distorted octahedral geometry defined by two O atoms from two terephthalate (tp) ligands, two O atoms from two 4,4′-bipyridine N,N′-dioxide (bpydo) ligands and two water molecules. The coordinated tp and bpydo ligands and uncoordinated bpydo molecule all have an inversion center. The Co^II atoms are connected by the tp and bpydo ligands into a layer parallel to (111). In the crystal, O—H⋯O hydrogen bonds link the uncoordinated bpydo molecules and the layers into a three-dimensional supramolecular structure. Intralayer O—H⋯O hydrogen bonds and π–π interactions [centroid-to-centroid distances = 3.6643 (13) and 3.8048 (13) Å] are also observed.

Related literature

For the design of supramolecular structures containing metal ions and organic ligands, see: Liao et al. (2008 ); Wang et al. (2008 ). For a related structure, see: Su et al. (2009 ).

Experimental

Crystal data

[Co(C₈H₄O₄)(C₁₀H₈N₂O₂)(H₂O)₂]·C₁₀H₈N₂O₂
M_r = 635.44
Triclinic, $[P \overline 1]$
a = 7.3883 (10) Å
b = 9.1788 (13) Å
c = 9.8054 (13) Å
α = 81.312 (2)°
β = 82.200 (2)°
γ = 79.301 (2)°
V = 641.92 (15) Å³
Z = 1
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 293 K
0.27 × 0.24 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.825, T_max = 0.866
3574 measured reflections
2516 independent reflections
2340 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.081
S = 1.05
2516 reflections
202 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O2	0.84 (2)	1.92 (2)	2.755 (2)	170 (2)
O5—H5B⋯O3ⁱ	0.85 (2)	1.85 (2)	2.660 (2)	158 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812040056/hy2589sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812040056/hy2589Isup2.hkl

checkCIF report

Comment top

Much progress has been achieved in the design of supramolecular structures containing metal–organic molecules during recent years (Liao et al., 2008; Wang et al., 2008). Multifunctional ligands can link metal ions into one-, two- or three-dimensional structures, and in this context, aromatic carboxylates and 4,4'-bipyridine N,N'-dioxide have been used successfully to synthesize such materials.

As shown in Fig. 1, the coordination environment of the Co^II atom, lying on an inversion center, can be described as distorted octahedral, defined by four O atoms in the equatorial plane from two terephthalate (tp) ligands and two 4,4'-bipyridine N,N'-dioxide (bpydo) ligands, and two water molecules in the axial positions. The bond distances and angles are normal (Su et al., 2009). The Co^II atoms are connected by the tp and bpydo ligands, forming a layer structure parallel to (111). O—H···O hydrogen bonds (Table 1) link the uncoordinated bpydo molecules and the layers into a three-dimensional supramolecular structure (Fig. 2). Intralayer O—H···O hydrogen bonds and π–π interactions [centroid–centroid distances = 3.6643 (13) and 3.8048 (13) Å] are also observed.

Related literature top

For the design of supramolecular structures containing metal ions and organic ligands, see: Liao et al. (2008); Wang et al. (2008). For a related structure, see: Su et al. (2009).

Experimental top

A mixture of terephthalic acid (0.1 mmol, 0.017 g), 4,4'-bipyridine N,N'-dioxide (0.2 mmol, 0.038 g), cobalt nitrate (0.1 mmol, 0.030 g), H₂O (5 ml) and dimethylformamide (15 ml) was stirred at 358 K for 10 min. The mixture was filtrated and pink block crystals of the title compound were isolated after evaporation of the solvent.

Structure description top

For the design of supramolecular structures containing metal ions and organic ligands, see: Liao et al. (2008); Wang et al. (2008). For a related structure, see: Su et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 1 - x, 2 - y, -z; (iii) 2 - x, 1 - y, -z; (iv) 2 - x, 2 - y, -z.]
	Fig. 2. View of the three-dimensional structure of the title compound, built by hydrogen bonds (dashed lines).

Poly[[diaqua(µ-4,4'-bipyridine N,N'-dioxide-κ²O:O')(µ-terephthalato- κ²O¹:O⁴)cobalt(II)] 4,4'-bipyridine N,N'-dioxide monosolvate] top

Crystal data top

[Co(C₈H₄O₄)(C₁₀H₈N₂O₂)(H₂O)₂]·C₁₀H₈N₂O₂	Z = 1
M_r = 635.44	F(000) = 327
Triclinic, P1	D_x = 1.644 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3883 (10) Å	Cell parameters from 2899 reflections
b = 9.1788 (13) Å	θ = 2.3–26.1°
c = 9.8054 (13) Å	µ = 0.74 mm⁻¹
α = 81.312 (2)°	T = 293 K
β = 82.200 (2)°	Block, pink
γ = 79.301 (2)°	0.27 × 0.24 × 0.20 mm
V = 641.92 (15) Å³

Data collection top

Bruker APEXII CCD diffractometer	2516 independent reflections
Radiation source: fine-focus sealed tube	2340 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
φ and ω scans	θ_max = 26.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→9
T_min = 0.825, T_max = 0.866	k = −10→11
3574 measured reflections	l = −8→12

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0389P)² + 0.3924P] where P = (F_o² + 2F_c²)/3
2516 reflections	(Δ/σ)_max < 0.001
202 parameters	Δρ_max = 0.48 e Å⁻³
2 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Co(C₈H₄O₄)(C₁₀H₈N₂O₂)(H₂O)₂]·C₁₀H₈N₂O₂	γ = 79.301 (2)°
M_r = 635.44	V = 641.92 (15) Å³
Triclinic, P1	Z = 1
a = 7.3883 (10) Å	Mo Kα radiation
b = 9.1788 (13) Å	µ = 0.74 mm⁻¹
c = 9.8054 (13) Å	T = 293 K
α = 81.312 (2)°	0.27 × 0.24 × 0.20 mm
β = 82.200 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2516 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2340 reflections with I > 2σ(I)
T_min = 0.825, T_max = 0.866	R_int = 0.017
3574 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	2 restraints
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.48 e Å⁻³
2516 reflections	Δρ_min = −0.33 e Å⁻³
202 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.01630 (11)
C1	0.3852 (3)	0.7380 (2)	0.2083 (2)	0.0221 (4)
H1	0.3528	0.6439	0.2142	0.027*
C2	0.4275 (3)	0.8156 (2)	0.08038 (19)	0.0209 (4)
H2	0.4249	0.7727	0.0007	0.025*
C3	0.4745 (2)	0.9580 (2)	0.06822 (18)	0.0186 (4)
C4	0.4684 (3)	1.0181 (2)	0.1918 (2)	0.0233 (4)
H4	0.4925	1.1145	0.1887	0.028*
C5	0.4271 (3)	0.9365 (2)	0.3176 (2)	0.0242 (4)
H5	0.4246	0.9781	0.3988	0.029*
C6	0.8804 (3)	0.7935 (2)	0.2615 (2)	0.0270 (4)
H6	0.8534	0.6980	0.2909	0.032*
C7	0.9285 (3)	0.8359 (2)	0.1234 (2)	0.0264 (4)
H7	0.9313	0.7689	0.0606	0.032*
C8	0.9735 (3)	0.9770 (2)	0.0743 (2)	0.0217 (4)
C9	0.9655 (3)	1.0700 (2)	0.1762 (2)	0.0317 (5)
H9	0.9958	1.1649	0.1496	0.038*
C10	0.9150 (3)	1.0265 (2)	0.3131 (2)	0.0344 (5)
H10	0.9102	1.0920	0.3777	0.041*
C11	0.6942 (2)	0.44694 (19)	0.21107 (18)	0.0164 (4)
C12	0.8539 (2)	0.47312 (19)	0.10187 (18)	0.0162 (3)
C13	1.0328 (2)	0.46045 (19)	0.13839 (18)	0.0175 (4)
H13	1.0549	0.4345	0.2308	0.021*
C14	1.1778 (2)	0.4865 (2)	0.03689 (18)	0.0179 (4)
H14	1.2970	0.4770	0.0617	0.021*
N1	0.3901 (2)	0.79675 (17)	0.32562 (16)	0.0206 (3)
N2	0.8716 (2)	0.88841 (18)	0.35576 (18)	0.0254 (4)
O1	0.3567 (2)	0.71908 (15)	0.44822 (14)	0.0266 (3)
O2	0.8186 (2)	0.84874 (17)	0.48725 (15)	0.0350 (4)
O3	0.57776 (18)	0.37620 (15)	0.18300 (14)	0.0232 (3)
O4	0.68909 (17)	0.50355 (14)	0.32145 (12)	0.0194 (3)
O5	0.67652 (19)	0.59404 (15)	0.59885 (14)	0.0225 (3)
H5A	0.719 (3)	0.6689 (19)	0.555 (2)	0.034*
H5B	0.605 (3)	0.626 (3)	0.6676 (17)	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.01820 (19)	0.02037 (19)	0.01144 (18)	−0.00652 (13)	0.00000 (13)	−0.00296 (13)
C1	0.0249 (9)	0.0193 (9)	0.0237 (10)	−0.0039 (7)	−0.0069 (8)	−0.0034 (7)
C2	0.0255 (9)	0.0216 (9)	0.0175 (9)	−0.0037 (7)	−0.0071 (7)	−0.0046 (7)
C3	0.0171 (8)	0.0206 (9)	0.0179 (9)	−0.0003 (7)	−0.0048 (7)	−0.0026 (7)
C4	0.0280 (10)	0.0213 (9)	0.0218 (10)	−0.0048 (7)	−0.0024 (8)	−0.0057 (7)
C5	0.0301 (10)	0.0250 (10)	0.0188 (9)	−0.0041 (8)	−0.0018 (8)	−0.0081 (8)
C6	0.0300 (10)	0.0204 (9)	0.0310 (11)	−0.0082 (8)	0.0042 (8)	−0.0062 (8)
C7	0.0288 (10)	0.0210 (9)	0.0302 (11)	−0.0063 (8)	0.0028 (8)	−0.0086 (8)
C8	0.0179 (9)	0.0185 (9)	0.0289 (11)	−0.0020 (7)	−0.0020 (7)	−0.0048 (7)
C9	0.0451 (13)	0.0205 (10)	0.0318 (12)	−0.0132 (9)	−0.0024 (10)	−0.0026 (8)
C10	0.0504 (14)	0.0267 (11)	0.0304 (12)	−0.0155 (10)	−0.0029 (10)	−0.0080 (9)
C11	0.0182 (8)	0.0164 (8)	0.0137 (8)	−0.0020 (6)	−0.0012 (7)	−0.0008 (7)
C12	0.0190 (8)	0.0162 (8)	0.0141 (9)	−0.0044 (6)	0.0011 (7)	−0.0055 (7)
C13	0.0218 (9)	0.0200 (8)	0.0113 (8)	−0.0042 (7)	−0.0021 (7)	−0.0028 (7)
C14	0.0166 (8)	0.0217 (9)	0.0167 (9)	−0.0039 (7)	−0.0026 (7)	−0.0051 (7)
N1	0.0212 (8)	0.0229 (8)	0.0159 (8)	−0.0011 (6)	−0.0012 (6)	−0.0009 (6)
N2	0.0265 (8)	0.0251 (8)	0.0252 (9)	−0.0074 (7)	0.0007 (7)	−0.0043 (7)
O1	0.0343 (8)	0.0249 (7)	0.0168 (7)	−0.0022 (6)	0.0022 (6)	0.0016 (5)
O2	0.0473 (9)	0.0337 (8)	0.0253 (8)	−0.0170 (7)	0.0073 (7)	−0.0058 (6)
O3	0.0241 (7)	0.0301 (7)	0.0195 (7)	−0.0133 (6)	0.0022 (5)	−0.0095 (5)
O4	0.0221 (6)	0.0259 (7)	0.0123 (6)	−0.0093 (5)	0.0018 (5)	−0.0055 (5)
O5	0.0234 (7)	0.0282 (7)	0.0181 (7)	−0.0109 (6)	0.0008 (5)	−0.0048 (6)

Geometric parameters (Å, º) top

Co1—O4ⁱ	2.0865 (12)	C7—H7	0.9300
Co1—O4	2.0865 (12)	C8—C9	1.398 (3)
Co1—O5	2.0975 (13)	C8—C8ⁱⁱⁱ	1.475 (4)
Co1—O5ⁱ	2.0976 (13)	C9—C10	1.364 (3)
Co1—O1ⁱ	2.1141 (13)	C9—H9	0.9300
Co1—O1	2.1141 (13)	C10—N2	1.356 (3)
C1—N1	1.350 (2)	C10—H10	0.9300
C1—C2	1.373 (3)	C11—O3	1.250 (2)
C1—H1	0.9300	C11—O4	1.263 (2)
C2—C3	1.397 (3)	C11—C12	1.510 (2)
C2—H2	0.9300	C12—C14^iv	1.395 (2)
C3—C4	1.398 (3)	C12—C13	1.396 (2)
C3—C3ⁱⁱ	1.479 (4)	C13—C14	1.389 (3)
C4—C5	1.371 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—C12^iv	1.395 (2)
C5—N1	1.349 (3)	C14—H14	0.9300
C5—H5	0.9300	N1—O1	1.319 (2)
C6—N2	1.350 (3)	N2—O2	1.312 (2)
C6—C7	1.368 (3)	O5—H5A	0.84 (2)
C6—H6	0.9300	O5—H5B	0.85 (2)
C7—C8	1.395 (3)

O4ⁱ—Co1—O4	180.0	C6—C7—H7	119.1
O4ⁱ—Co1—O5	90.46 (5)	C8—C7—H7	119.1
O4—Co1—O5	89.54 (5)	C7—C8—C9	115.04 (18)
O4ⁱ—Co1—O5ⁱ	89.54 (5)	C7—C8—C8ⁱⁱⁱ	122.1 (2)
O4—Co1—O5ⁱ	90.46 (5)	C9—C8—C8ⁱⁱⁱ	122.9 (2)
O5—Co1—O5ⁱ	180.00 (6)	C10—C9—C8	122.32 (19)
O4ⁱ—Co1—O1ⁱ	95.05 (5)	C10—C9—H9	118.8
O4—Co1—O1ⁱ	84.95 (5)	C8—C9—H9	118.8
O5—Co1—O1ⁱ	92.31 (6)	N2—C10—C9	120.4 (2)
O5ⁱ—Co1—O1ⁱ	87.69 (6)	N2—C10—H10	119.8
O4ⁱ—Co1—O1	84.95 (5)	C9—C10—H10	119.8
O4—Co1—O1	95.05 (5)	O3—C11—O4	126.25 (16)
O5—Co1—O1	87.69 (6)	O3—C11—C12	117.81 (15)
O5ⁱ—Co1—O1	92.31 (6)	O4—C11—C12	115.90 (15)
O1ⁱ—Co1—O1	180.0	C14^iv—C12—C13	119.39 (16)
N1—C1—C2	120.77 (17)	C14^iv—C12—C11	119.82 (15)
N1—C1—H1	119.6	C13—C12—C11	120.77 (15)
C2—C1—H1	119.6	C14—C13—C12	120.09 (16)
C1—C2—C3	120.92 (17)	C14—C13—H13	120.0
C1—C2—H2	119.5	C12—C13—H13	120.0
C3—C2—H2	119.5	C13—C14—C12^iv	120.52 (16)
C2—C3—C4	116.56 (17)	C13—C14—H14	119.7
C2—C3—C3ⁱⁱ	121.9 (2)	C12^iv—C14—H14	119.7
C4—C3—C3ⁱⁱ	121.5 (2)	O1—N1—C5	119.74 (16)
C5—C4—C3	120.68 (18)	O1—N1—C1	120.43 (16)
C5—C4—H4	119.7	C5—N1—C1	119.82 (16)
C3—C4—H4	119.7	O2—N2—C6	120.49 (16)
N1—C5—C4	121.11 (17)	O2—N2—C10	120.07 (17)
N1—C5—H5	119.4	C6—N2—C10	119.44 (18)
C4—C5—H5	119.4	N1—O1—Co1	121.82 (11)
N2—C6—C7	120.93 (18)	C11—O4—Co1	130.60 (11)
N2—C6—H6	119.5	Co1—O5—H5A	117.3 (17)
C7—C6—H6	119.5	Co1—O5—H5B	102.4 (17)
C6—C7—C8	121.82 (19)	H5A—O5—H5B	106 (2)

N1—C1—C2—C3	−0.8 (3)	C4—C5—N1—C1	−3.0 (3)
C1—C2—C3—C4	−2.5 (3)	C2—C1—N1—O1	−177.21 (16)
C1—C2—C3—C3ⁱⁱ	178.3 (2)	C2—C1—N1—C5	3.6 (3)
C2—C3—C4—C5	3.1 (3)	C7—C6—N2—O2	177.42 (19)
C3ⁱⁱ—C3—C4—C5	−177.7 (2)	C7—C6—N2—C10	−1.4 (3)
C3—C4—C5—N1	−0.5 (3)	C9—C10—N2—O2	−178.3 (2)
N2—C6—C7—C8	1.1 (3)	C9—C10—N2—C6	0.5 (3)
C6—C7—C8—C9	0.0 (3)	C5—N1—O1—Co1	−128.29 (15)
C6—C7—C8—C8ⁱⁱⁱ	179.6 (2)	C1—N1—O1—Co1	52.5 (2)
C7—C8—C9—C10	−0.9 (3)	O4ⁱ—Co1—O1—N1	−171.81 (14)
C8ⁱⁱⁱ—C8—C9—C10	179.5 (2)	O4—Co1—O1—N1	8.19 (14)
C8—C9—C10—N2	0.6 (4)	O5—Co1—O1—N1	97.52 (14)
O3—C11—C12—C14^iv	42.0 (2)	O5ⁱ—Co1—O1—N1	−82.48 (14)
O4—C11—C12—C14^iv	−135.93 (17)	O3—C11—O4—Co1	2.1 (3)
O3—C11—C12—C13	−139.35 (17)	C12—C11—O4—Co1	179.77 (11)
O4—C11—C12—C13	42.7 (2)	O5—Co1—O4—C11	170.87 (15)
C14^iv—C12—C13—C14	−0.6 (3)	O5ⁱ—Co1—O4—C11	−9.13 (15)
C11—C12—C13—C14	−179.28 (16)	O1ⁱ—Co1—O4—C11	78.51 (15)
C12—C13—C14—C12^iv	0.6 (3)	O1—Co1—O4—C11	−101.49 (15)
C4—C5—N1—O1	177.84 (17)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2	0.84 (2)	1.92 (2)	2.755 (2)	170 (2)
O5—H5B···O3ⁱ	0.85 (2)	1.85 (2)	2.660 (2)	158 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Co(C₈H₄O₄)(C₁₀H₈N₂O₂)(H₂O)₂]·C₁₀H₈N₂O₂
M_r	635.44
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.3883 (10), 9.1788 (13), 9.8054 (13)
α, β, γ (°)	81.312 (2), 82.200 (2), 79.301 (2)
V (Å³)	641.92 (15)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.27 × 0.24 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.825, 0.866
No. of measured, independent and observed [I > 2σ(I)] reflections	3574, 2516, 2340
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.081, 1.05
No. of reflections	2516
No. of parameters	202
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2	0.84 (2)	1.92 (2)	2.755 (2)	170 (2)
O5—H5B···O3ⁱ	0.85 (2)	1.85 (2)	2.660 (2)	158 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors are grateful for financial aid from the National Natural Science Foundation of China (grant No. 21001101).

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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