Poly[(acetato-κ2O,O′)aqua­(μ4-1H-benzimidazole-5,6-dicarboxyl­ato-κ6N3:O5,O5′:O5,O6:O6′)cerium(III)]

Chen, J.; Wang, Y.; Zheng, C.; Luo, Y.

doi:10.1107/S1600536812017503

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page m673

doi:10.1107/S1600536812017503

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Poly[(acetato-κ²O,O′)aqua(μ₄-1H-benzimidazole-5,6-dicarboxylato-κ⁶N³:O⁵,O^5′:O⁵,O⁶:O^6′)cerium(III)]

Jinhua Chen,^a Yuezhu Wang,^a Chun Zheng ^a and Yifan Luo ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: luoyf2010@yahoo.com.cn

(Received 20 March 2012; accepted 19 April 2012; online 25 April 2012)

In the title compound, [Ce(C₉H₄N₂O₄)(C₂H₃O₂)(H₂O)]_n, the Ce^III ion is coordinated by five O atoms and one N atom from four 1H-benzimidazole-5,6-dicarboxylato (L) ligands and by two O atoms from an acetate ligand and one aqua ligand, forming a slightly distorted tricapped trigonal–prismatic geometry. The L ligands are bridging, forming a layered polymer parallel to (010). In the crystal, O—H⋯O and N—H⋯O hydrogen bonds connect the polymer layers into a three-dimensional network.

Related literature

For background to 1H-benzimidazole-5,6-dicarboxylate complexes and for related structures, see: Gao et al. (2008 ); Yao et al. (2008 ); Song, Wang, Hu et al. (2009 ); Song, Wang, Li et al. (2009 ).

Experimental

Crystal data

[Ce(C₉H₄N₂O₄)(C₂H₃O₂)(H₂O)]
M_r = 421.32
Triclinic, $[P \overline 1]$
a = 7.4577 (15) Å
b = 9.0399 (19) Å
c = 9.792 (2) Å
α = 86.895 (2)°
β = 86.510 (2)°
γ = 84.707 (2)°
V = 655.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 3.51 mm⁻¹
T = 293 K
0.17 × 0.13 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.584, T_max = 0.680
3390 measured reflections
2366 independent reflections
2194 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.054
S = 1.05
2321 reflections
203 parameters
130 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O5ⁱ	0.86 (3)	1.93 (3)	2.716 (4)	153 (4)
O7—H7A⋯O3ⁱⁱ	0.84 (4)	2.05 (4)	2.850 (4)	158 (3)
O7—H7B⋯O6ⁱⁱⁱ	0.83 (3)	1.95 (3)	2.777 (4)	176 (6)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812017503/lh5440sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017503/lh5440Isup2.hkl

checkCIF report

Comment top

1H-Benzimidazole-5,6-dicarboxylic acid (H₂L) acts as a multidentate ligand forming coordination polymers (Gao et al., 2008; Yao et al., 2008; Song, Wang, Hu et al., 2009; Song, Wang, Li et al., 2009). Herein, we report the Ce(III) complex of H₂L. The asymmetric unit of the title compound with additional symmetry related atoms is shown in Fig. 1. The Ce^III ion is coordinated by five O atoms and one N atom originating from four 1H-benzimidazole-5,6-dicarboxylate (L) ligands along with two O atoms from an acetate ligand and one aqua ligand forming a slightly distorted tricapped trigonal-prismatic geometry. The L ligands act as bridging forming a layered polymer parallel to (010) (Fig. 2). In the crystal, intermolecular O—H···O and N—H···O hydrogen bonds connect the polymer layers into a three-dimensional network.

Related literature top

For background to 1H-benzimidazole-5,6-dicarboxylate complexes and for related structures, see: Gao et al. (2008); Yao et al. (2008); Song, Wang, Hu et al. (2009); Song, Wang, Li et al. (2009).

Experimental top

A mixture of Ce₂O₃ (0.4 mmol), H₂L (0.4 mmol), acetic acid (0.4 mmol) and water (13 ml) was added in a 25 ml teflon-lined stainless container, which was heated at 453 K for 3 days. After cooling to room temperature, colorless crystals were recovered by filtration.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The asymmetric unit of the title compound, together with some symmetry related atoms to complete the coordination of the Ce^III ion. Displacement ellipsoids are shown at the 50% probability level. [Symmetry codes: (a) = -x, 1-y, 2-z; (b )= 1-x, 1-y, 2-z; (c) = 1+x, y, z; (d) = 1-x, 1-y, 1-z; (e) = x, y, -1+z; (f) = -x, 1-y, 1-z; (g) = -1+x, y, z; (h) = x, y, 1+z].
	Fig. 2. Part of the crystal structure showing polymeric layers parallel to the ac plane. H atoms are not showm.

Poly[(acetato-κ²O,O')aqua(µ₄-1H-benzimidazole-5,6- dicarboxylato- κ⁶N³:O⁵,O^5':O⁵,O⁶: O^6')cerium(III)] top

Crystal data top

[Ce(C₉H₄N₂O₄)(C₂H₃O₂)(H₂O)]	Z = 2
M_r = 421.32	F(000) = 406
Triclinic, P1	D_x = 2.135 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4577 (15) Å	Cell parameters from 2613 reflections
b = 9.0399 (19) Å	θ = 2.1–25.2°
c = 9.792 (2) Å	µ = 3.51 mm⁻¹
α = 86.895 (2)°	T = 293 K
β = 86.510 (2)°	Block, colorless
γ = 84.707 (2)°	0.17 × 0.13 × 0.11 mm
V = 655.3 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	2366 independent reflections
Radiation source: fine-focus sealed tube	2194 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.584, T_max = 0.680	k = −10→7
3390 measured reflections	l = −11→10

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0217P)² + 1.2938P] where P = (F_o² + 2F_c²)/3
2321 reflections	(Δ/σ)_max = 0.004
203 parameters	Δρ_max = 0.74 e Å⁻³
130 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Ce(C₉H₄N₂O₄)(C₂H₃O₂)(H₂O)]	γ = 84.707 (2)°
M_r = 421.32	V = 655.3 (2) Å³
Triclinic, P1	Z = 2
a = 7.4577 (15) Å	Mo Kα radiation
b = 9.0399 (19) Å	µ = 3.51 mm⁻¹
c = 9.792 (2) Å	T = 293 K
α = 86.895 (2)°	0.17 × 0.13 × 0.11 mm
β = 86.510 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2366 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2194 reflections with I > 2σ(I)
T_min = 0.584, T_max = 0.680	R_int = 0.016
3390 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	130 restraints
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.74 e Å⁻³
2321 reflections	Δρ_min = −0.59 e Å⁻³
203 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.

The number of independent reflections and the number of reflections used in the refinement are not the same,because we used 'omit -3 50' to enhance the '_diffrn_measured_fraction_theta_full'.

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

	x	y	z	U_iso*/U_eq
Ce1	0.35253 (3)	0.35579 (2)	0.893484 (19)	0.01339 (8)
O6	0.3692 (4)	0.0660 (3)	0.8693 (3)	0.0242 (6)
O5	0.5196 (3)	0.1955 (3)	0.7120 (3)	0.0224 (6)
O3	0.1354 (3)	0.5879 (3)	0.8893 (3)	0.0198 (6)
O4	0.1202 (3)	0.2775 (3)	1.0582 (2)	0.0181 (5)
O7	0.6258 (4)	0.2197 (3)	1.0107 (3)	0.0277 (7)
O1	0.4775 (3)	0.5295 (3)	0.7017 (3)	0.0235 (6)
O2	0.6399 (3)	0.5169 (3)	0.8819 (2)	0.0169 (5)
N1	0.1240 (4)	0.3026 (3)	0.7095 (3)	0.0185 (7)
N2	−0.1340 (4)	0.2436 (4)	0.6341 (3)	0.0199 (7)
C4	0.1286 (5)	0.3230 (4)	0.5663 (3)	0.0152 (7)
C5	−0.0343 (5)	0.2557 (4)	0.7418 (4)	0.0189 (8)
H5	−0.0745	0.2328	0.8315	0.023*
C6	−0.0331 (5)	0.2865 (4)	0.5188 (4)	0.0157 (7)
C7	−0.0694 (5)	0.3027 (4)	0.3812 (4)	0.0175 (8)
H7	−0.1804	0.2823	0.3516	0.021*
C3	0.2613 (5)	0.3736 (4)	0.4746 (4)	0.0147 (7)
H3	0.3695	0.3983	0.5059	0.018*
C2	0.2310 (5)	0.3871 (4)	0.3353 (3)	0.0130 (7)
C8	0.0645 (5)	0.3502 (4)	0.2889 (4)	0.0141 (7)
C10	0.4720 (5)	0.0728 (4)	0.7632 (4)	0.0235 (9)
C1	0.6200 (5)	0.5515 (4)	0.7549 (3)	0.0129 (7)
C9	−0.0166 (5)	0.6502 (4)	0.8595 (3)	0.0139 (7)
C11	0.5451 (11)	−0.0663 (6)	0.6954 (7)	0.084 (3)
H11A	0.6391	−0.1166	0.7478	0.126*
H11B	0.5930	−0.0413	0.6047	0.126*
H11C	0.4501	−0.1302	0.6901	0.126*
H7B	0.629 (6)	0.133 (3)	1.043 (5)	0.037 (14)*
H7A	0.717 (5)	0.259 (4)	1.032 (5)	0.045 (15)*
H2	−0.239 (3)	0.212 (5)	0.635 (5)	0.045 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ce1	0.01261 (12)	0.01670 (12)	0.01084 (11)	−0.00151 (8)	0.00020 (7)	−0.00120 (7)
O6	0.0253 (15)	0.0189 (14)	0.0274 (16)	−0.0020 (11)	0.0036 (12)	0.0014 (11)
O5	0.0166 (14)	0.0236 (15)	0.0257 (15)	0.0007 (11)	0.0058 (11)	−0.0019 (11)
O3	0.0172 (13)	0.0229 (14)	0.0189 (14)	0.0031 (11)	−0.0064 (11)	−0.0008 (11)
O4	0.0163 (13)	0.0249 (14)	0.0136 (13)	−0.0032 (11)	0.0028 (10)	−0.0062 (11)
O7	0.0244 (16)	0.0199 (15)	0.0401 (18)	−0.0023 (12)	−0.0165 (13)	0.0038 (13)
O1	0.0175 (14)	0.0368 (17)	0.0175 (14)	−0.0121 (12)	−0.0027 (11)	0.0062 (12)
O2	0.0178 (13)	0.0223 (14)	0.0114 (13)	−0.0066 (10)	−0.0004 (10)	0.0007 (10)
N1	0.0183 (16)	0.0247 (17)	0.0127 (15)	−0.0045 (13)	−0.0003 (12)	0.0010 (12)
N2	0.0151 (17)	0.0302 (19)	0.0146 (16)	−0.0066 (14)	0.0024 (13)	0.0016 (13)
C4	0.0174 (18)	0.0187 (18)	0.0090 (17)	0.0005 (14)	0.0004 (14)	−0.0010 (13)
C5	0.022 (2)	0.025 (2)	0.0090 (17)	−0.0024 (16)	0.0026 (14)	0.0013 (14)
C6	0.0124 (18)	0.0185 (19)	0.0153 (18)	−0.0013 (14)	0.0044 (14)	0.0015 (14)
C7	0.0126 (18)	0.024 (2)	0.0168 (19)	−0.0046 (15)	−0.0010 (14)	−0.0016 (15)
C3	0.0118 (17)	0.0191 (19)	0.0137 (18)	−0.0014 (14)	−0.0022 (14)	−0.0027 (14)
C2	0.0127 (17)	0.0126 (17)	0.0134 (17)	0.0004 (13)	0.0004 (14)	−0.0008 (13)
C8	0.0107 (17)	0.0172 (18)	0.0135 (18)	0.0037 (13)	−0.0006 (13)	−0.0003 (14)
C10	0.025 (2)	0.021 (2)	0.024 (2)	0.0016 (16)	0.0007 (17)	−0.0019 (16)
C1	0.0138 (18)	0.0101 (16)	0.0145 (18)	0.0017 (13)	−0.0010 (14)	−0.0013 (13)
C9	0.0136 (18)	0.0158 (18)	0.0127 (18)	−0.0054 (14)	0.0003 (14)	0.0019 (14)
C11	0.139 (7)	0.025 (3)	0.079 (5)	0.006 (3)	0.060 (5)	−0.014 (3)

Geometric parameters (Å, º) top

Ce1—O4	2.422 (2)	N2—C5	1.342 (5)
Ce1—O3	2.529 (3)	N2—C6	1.376 (4)
Ce1—O2ⁱ	2.543 (2)	N2—H2	0.857 (10)
Ce1—O5	2.547 (3)	C4—C3	1.388 (5)
Ce1—O1	2.568 (2)	C4—C6	1.392 (5)
Ce1—O7	2.580 (3)	C5—H5	0.9300
Ce1—O6	2.634 (3)	C6—C7	1.388 (5)
Ce1—N1	2.646 (3)	C7—C8	1.388 (5)
Ce1—O2	2.693 (2)	C7—H7	0.9300
Ce1—C10	2.960 (4)	C3—C2	1.394 (5)
Ce1—C1	3.002 (3)	C3—H3	0.9300
O6—C10	1.256 (5)	C2—C8	1.422 (5)
O5—C10	1.265 (5)	C2—C1ⁱⁱⁱ	1.505 (5)
O3—C9	1.262 (4)	C8—C9^iv	1.518 (5)
O4—C9ⁱⁱ	1.249 (4)	C10—C11	1.496 (6)
O7—H7B	0.830 (18)	C1—C2ⁱⁱⁱ	1.505 (5)
O7—H7A	0.837 (18)	C9—O4ⁱⁱ	1.249 (4)
O1—C1	1.248 (4)	C9—C8^iv	1.518 (5)
O2—C1	1.280 (4)	C11—H11A	0.9600
O2—Ce1ⁱ	2.543 (2)	C11—H11B	0.9600
N1—C5	1.306 (5)	C11—H11C	0.9600
N1—C4	1.403 (5)

O4—Ce1—O3	80.07 (8)	C9—O3—Ce1	148.6 (2)
O4—Ce1—O2ⁱ	68.71 (8)	C9ⁱⁱ—O4—Ce1	131.1 (2)
O3—Ce1—O2ⁱ	70.91 (8)	Ce1—O7—H7B	124 (3)
O4—Ce1—O5	125.69 (8)	Ce1—O7—H7A	126 (3)
O3—Ce1—O5	134.99 (8)	H7B—O7—H7A	110 (3)
O2ⁱ—Ce1—O5	148.20 (8)	C1—O1—Ce1	97.7 (2)
O4—Ce1—O1	153.50 (9)	C1—O2—Ce1ⁱ	139.2 (2)
O3—Ce1—O1	74.17 (9)	C1—O2—Ce1	90.97 (19)
O2ⁱ—Ce1—O1	107.59 (8)	Ce1ⁱ—O2—Ce1	109.06 (8)
O5—Ce1—O1	71.89 (9)	C5—N1—C4	104.1 (3)
O4—Ce1—O7	97.53 (9)	C5—N1—Ce1	123.3 (2)
O3—Ce1—O7	144.86 (9)	C4—N1—Ce1	132.5 (2)
O2ⁱ—Ce1—O7	75.57 (9)	C5—N2—C6	107.0 (3)
O5—Ce1—O7	74.44 (9)	C5—N2—H2	127 (3)
O1—Ce1—O7	107.06 (9)	C6—N2—H2	126 (3)
O4—Ce1—O6	76.55 (8)	C3—C4—C6	120.0 (3)
O3—Ce1—O6	142.29 (8)	C3—C4—N1	130.5 (3)
O2ⁱ—Ce1—O6	125.00 (8)	C6—C4—N1	109.5 (3)
O5—Ce1—O6	50.21 (8)	N1—C5—N2	114.1 (3)
O1—Ce1—O6	121.56 (9)	N1—C5—H5	122.9
O7—Ce1—O6	68.14 (9)	N2—C5—H5	122.9
O4—Ce1—N1	84.39 (9)	N2—C6—C7	132.6 (3)
O3—Ce1—N1	76.65 (9)	N2—C6—C4	105.3 (3)
O2ⁱ—Ce1—N1	140.60 (9)	C7—C6—C4	122.0 (3)
O5—Ce1—N1	71.10 (9)	C8—C7—C6	118.1 (3)
O1—Ce1—N1	83.75 (9)	C8—C7—H7	121.0
O7—Ce1—N1	138.34 (10)	C6—C7—H7	121.0
O6—Ce1—N1	72.00 (9)	C4—C3—C2	119.4 (3)
O4—Ce1—O2	139.30 (8)	C4—C3—H3	120.3
O3—Ce1—O2	91.88 (8)	C2—C3—H3	120.3
O2ⁱ—Ce1—O2	70.94 (9)	C3—C2—C8	119.8 (3)
O5—Ce1—O2	87.74 (8)	C3—C2—C1ⁱⁱⁱ	115.2 (3)
O1—Ce1—O2	49.17 (8)	C8—C2—C1ⁱⁱⁱ	124.9 (3)
O7—Ce1—O2	67.05 (8)	C7—C8—C2	120.7 (3)
O6—Ce1—O2	124.89 (8)	C7—C8—C9^iv	113.4 (3)
N1—Ce1—O2	132.72 (8)	C2—C8—C9^iv	125.8 (3)
O4—Ce1—C10	101.21 (10)	O6—C10—O5	121.6 (4)
O3—Ce1—C10	146.18 (10)	O6—C10—C11	120.3 (4)
O2ⁱ—Ce1—C10	141.48 (9)	O5—C10—C11	118.1 (4)
O5—Ce1—C10	25.14 (10)	O6—C10—Ce1	62.8 (2)
O1—Ce1—C10	96.82 (10)	O5—C10—Ce1	58.8 (2)
O7—Ce1—C10	68.91 (10)	C11—C10—Ce1	176.0 (4)
O6—Ce1—C10	25.08 (9)	O1—C1—O2	120.3 (3)
N1—Ce1—C10	69.91 (10)	O1—C1—C2ⁱⁱⁱ	118.3 (3)
O2—Ce1—C10	106.88 (10)	O2—C1—C2ⁱⁱⁱ	121.4 (3)
O4—Ce1—C1	158.49 (9)	O1—C1—Ce1	57.99 (18)
O3—Ce1—C1	85.24 (9)	O2—C1—Ce1	63.79 (17)
O2ⁱ—Ce1—C1	91.70 (9)	C2ⁱⁱⁱ—C1—Ce1	164.7 (2)
O5—Ce1—C1	75.70 (9)	O4ⁱⁱ—C9—O3	123.6 (3)
O1—Ce1—C1	24.32 (9)	O4ⁱⁱ—C9—C8^iv	119.0 (3)
O7—Ce1—C1	85.50 (9)	O3—C9—C8^iv	117.0 (3)
O6—Ce1—C1	123.78 (9)	C10—C11—H11A	109.5
N1—Ce1—C1	107.48 (9)	C10—C11—H11B	109.5
O2—Ce1—C1	25.24 (8)	H11A—C11—H11B	109.5
C10—Ce1—C1	99.75 (10)	C10—C11—H11C	109.5
C10—O6—Ce1	92.2 (2)	H11A—C11—H11C	109.5
C10—O5—Ce1	96.0 (2)	H11B—C11—H11C	109.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5^v	0.86 (3)	1.93 (3)	2.716 (4)	153 (4)
O7—H7A···O3ⁱ	0.84 (4)	2.05 (4)	2.850 (4)	158 (3)
O7—H7B···O6^vi	0.83 (3)	1.95 (3)	2.777 (4)	176 (6)

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

Experimental details

Crystal data
Chemical formula	[Ce(C₉H₄N₂O₄)(C₂H₃O₂)(H₂O)]
M_r	421.32
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.4577 (15), 9.0399 (19), 9.792 (2)
α, β, γ (°)	86.895 (2), 86.510 (2), 84.707 (2)
V (Å³)	655.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.51
Crystal size (mm)	0.17 × 0.13 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.584, 0.680
No. of measured, independent and observed [I > 2σ(I)] reflections	3390, 2366, 2194
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.054, 1.05
No. of reflections	2321
No. of parameters	203
No. of restraints	130
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.59

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5ⁱ	0.86 (3)	1.93 (3)	2.716 (4)	153 (4)
O7—H7A···O3ⁱⁱ	0.84 (4)	2.05 (4)	2.850 (4)	158 (3)
O7—H7B···O6ⁱⁱⁱ	0.83 (3)	1.95 (3)	2.777 (4)	176 (6)

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

Acknowledgements

The authors acknowledge the Chan Xue Yan Cooperative Special Project of Guangdong Province and the Ministry of Science and Technology of the People's Republic of China (project No. 2010B090400184) and the Special Project of Science and Technology of Guangzhou City (project No. 2011 J4300063).

References

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