Tetra­aquabis(6-carboxy-1H-benzimid­azole-5-carboxyl­ato-κN3)nickel(II) dimethyl­formamide disolvate dihydrate

Wang, H.; Song, W.-D.; Li, S.-J.; Qin, P.-W.; Hu, S.-W.

doi:10.1107/S1600536809038069

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page m1258

doi:10.1107/S1600536809038069

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Tetraaquabis(6-carboxy-1H-benzimidazole-5-carboxylato-κN³)nickel(II) dimethylformamide disolvate dihydrate

Hao Wang,^a Wen-Dong Song,^b ^* Shi-Jie Li,^a Pei-Wen Qin ^c and Shi-Wei Hu ^a

^aCollege of Food Science and Technology, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China, ^bCollege of Science, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China, and ^cCollege of Agriculture, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
^*Correspondence e-mail: songwd60@163.com

(Received 20 September 2009; accepted 20 September 2009; online 30 September 2009)

The title compound, [Ni(C₉H₄₅N₂O₄)₂(H₂O)₄]·2C₃H₇NO·2H₂O, has the Ni^II center coordinated by four water molecules and two N atoms from two 1H-benzimidazole-5,6-dicarboxylate ligands in an octahedral geometry. The molecule interacts with the solvent water and dimethylformamide molecules through N—H⋯O and O—H⋯O hydrogen bonds to form a three-dimensional supramolecular network. The metal atom lies on a center of inversion.

Related literature

For the crystal structures of 1H-benzimidazole-5,6-dicarboxylate complexes, see: Gao et al. (2008 ); Lo et al. (2007 ); Song et al. (2009 ).

Experimental

Crystal data

[Ni(C₉H₅N₂O₄)₂(H₂O)₄]·2C₃H₇NO·2H₂O
M_r = 723.30
Triclinic, $[P \overline 1]$
a = 8.5327 (17) Å
b = 9.1387 (18) Å
c = 11.624 (2) Å
α = 100.80 (3)°
β = 103.03 (3)°
γ = 114.04 (3)°
V = 765.7 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.72 mm⁻¹
T = 293 K
0.27 × 0.18 × 0.17 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.830, T_max = 0.888
6116 measured reflections
2737 independent reflections
2613 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.137
S = 1.20
2737 reflections
217 parameters
9 restraints
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W⋯O1ⁱ	0.84	1.86	2.693 (3)	173
O1W—H1W⋯O3ⁱⁱ	0.84	2.00	2.801 (3)	160
O4—H4A⋯O5ⁱⁱⁱ	0.82	1.78	2.585 (3)	167
O2W—H4W⋯O2^iv	0.84	1.79	2.624 (3)	176
O2W—H3W⋯O1W^v	0.84	1.92	2.741 (2)	166
O3W—H5W⋯O1W^v	0.84	2.06	2.810 (3)	148
O3W—H6W⋯O1^vi	0.84	1.81	2.634 (3)	169
N2—H2⋯O5^vii	0.86	1.98	2.779 (3)	155
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x, y, z+1; (iii) -x+1, -y+2, -z; (iv) x-1, y-1, z; (v) -x+1, -y+1, -z+1; (vi) -x+2, -y+2, -z+1; (vii) -x, -y+1, -z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL9.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038069/ng2646sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809038069/ng2646Isup2.hkl

checkCIF report

Comment top

From the structuralpoint of view, 1H-benzimidazole-5,6-dicarboxylic acid possesses two nitrogen atoms of imidazole ring and four oxygen atoms of carboxylate groups, and might be used as versatile linker in constructing coordination polymers with abundant hydrogen bonds. And several coordination polymers fomed by this ligand have been reported recently:Pentaaqua(1H-benzimidazole-5,6-dicarboxylato-kN³)copper(II) pentahydrate(Gao et al.,2008), Bis(1H-benzimidazole-5,6-dicarboxylato)bis[tetraaquadicobalt(II)] pentahydrate(Lo et al.,2007), Pentaaqua(1H-benzimidazole-5,6-dicarboxylato-kN³) cobalt(II)pentahydrate(Song et al.,2009).In the present paper, we synthesized a novel coordination complex [Ni(C₉H₄N₂O₄)₂(H₂O)₄].2H₂O.2C₃H₇NO.

As shown in Figure 1, the Ni^II atom exhibits an octahedral coordination sphere, defined by two N atoms from two different 1H-benzimidazole-5,6-dicarboxylate ligands, and four water molecules. The equatorial plane is defined by O2w, O3w, O2wⁱ and O3wⁱ atoms, while N1 and N1ⁱ occupy the axial position (symmetry codes: i = 1 - x, 1 - y, 1 - z). Inter/intramolecular O—H···O and N—H···O hydrogen bonds between the carboxylate O atoms of 1H-benzimidazole-5,6-dicarboxylate and the coordinated water molecule lead to the structure more stable(Fig 2).The hydrogen bonds are in the normal range(Table 1).

Related literature top

For the crystal structures of 1H-benzimidazole-5,6-dicarboxylate complexes, see: Gao et al. (2008); Lo et al. (2007); Song et al. (2009).

Experimental top

A C₃H₇NO solution (20 mL)containing Ni(NO₃)₂(0.1 mmol)and 1H-benzimidazole-5,6-dicarboxylic acid(0.2 mmol) was stirred for a few minutes in air,and left to stand at room temperature for about four weeks, then the green crystals were obtained.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL9 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound, showing the atomic numbering scheme with 30% probability displacement ellipsoids. [Symmetry codes: (i) 1 - x, 1 - y, 1 - z.]
	Fig. 2. A view of the three-dimensional network constructed by O—H···O and N—H···O hydrogen bonding interactions.

Tetraaquabis(6-carboxy-1H-benzimidazole-5-carboxylato- κN³)nickel(II) dimethylformamide disolvate dihydrate top

Crystal data top

[Ni(C₉H₅N₂O₄)₂(H₂O)₄]·2C₃H₇NO·2H₂O	Z = 1
M_r = 723.30	F(000) = 378
Triclinic, P1	D_x = 1.569 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5327 (17) Å	Cell parameters from 3600 reflections
b = 9.1387 (18) Å	θ = 1.4–28°
c = 11.624 (2) Å	µ = 0.72 mm⁻¹
α = 100.80 (3)°	T = 293 K
β = 103.03 (3)°	Block, green
γ = 114.04 (3)°	0.27 × 0.18 × 0.17 mm
V = 765.7 (3) Å³

Data collection top

Rigaku/MSC Mercury CCD diffractometer	2737 independent reflections
Radiation source: fine-focus sealed tube	2613 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 25.2°, θ_min = 3.3°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −10→10
T_min = 0.830, T_max = 0.888	k = −10→9
6116 measured reflections	l = −13→13

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) = 0.137	H-atom parameters constrained
S = 1.20	w = 1/[σ²(F_o²) + (0.1051P)² + 0.01P] where P = (F_o² + 2F_c²)/3
2737 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.61 e Å⁻³
9 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Ni(C₉H₅N₂O₄)₂(H₂O)₄]·2C₃H₇NO·2H₂O	γ = 114.04 (3)°
M_r = 723.30	V = 765.7 (3) Å³
Triclinic, P1	Z = 1
a = 8.5327 (17) Å	Mo Kα radiation
b = 9.1387 (18) Å	µ = 0.72 mm⁻¹
c = 11.624 (2) Å	T = 293 K
α = 100.80 (3)°	0.27 × 0.18 × 0.17 mm
β = 103.03 (3)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	2737 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	2613 reflections with I > 2σ(I)
T_min = 0.830, T_max = 0.888	R_int = 0.020
6116 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	9 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.20	Δρ_max = 0.61 e Å⁻³
2737 reflections	Δρ_min = −0.32 e Å⁻³
217 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
C1	0.2895 (3)	0.4030 (3)	0.2261 (2)	0.0301 (5)
H1	0.2030	0.3062	0.2339	0.036*
N1	0.4387 (2)	0.5153 (2)	0.31852 (17)	0.0272 (4)
Ni1	0.5000	0.5000	0.5000	0.02200 (19)
C2	0.4271 (3)	0.5938 (3)	0.1432 (2)	0.0272 (5)
N2	0.2739 (2)	0.4415 (2)	0.11945 (17)	0.0324 (4)
H2	0.1861	0.3832	0.0499	0.039*
C3	0.5296 (3)	0.6391 (3)	0.2686 (2)	0.0252 (4)
O3W	0.75996 (16)	0.54366 (16)	0.50333 (12)	0.0345 (4)
C4	0.6923 (3)	0.7892 (3)	0.3224 (2)	0.0271 (5)
H4	0.7612	0.8210	0.4056	0.033*
C5	0.7498 (3)	0.8909 (3)	0.2494 (2)	0.0248 (4)
O1	0.9319 (2)	1.1775 (2)	0.37262 (18)	0.0456 (5)
C6	0.6429 (3)	0.8423 (3)	0.1223 (2)	0.0280 (5)
O2	1.0690 (2)	1.0376 (2)	0.3063 (2)	0.0522 (5)
C7	0.4811 (3)	0.6925 (3)	0.0690 (2)	0.0307 (5)
H7	0.4113	0.6596	−0.0141	0.037*
C8	0.6944 (3)	0.9451 (3)	0.0384 (2)	0.0327 (5)
C9	0.9321 (3)	1.0500 (3)	0.31293 (19)	0.0261 (5)
O2W	0.41483 (16)	0.24688 (15)	0.42925 (12)	0.0295 (4)
H6W	0.8553	0.6369	0.5347	0.044*
H5W	0.7568	0.4874	0.4361	0.044*
H3W	0.4755	0.2330	0.3845	0.044*
H4W	0.3028	0.1830	0.3922	0.044*
O3	0.6082 (3)	0.8962 (3)	−0.07127 (17)	0.0591 (6)
O4	0.8343 (3)	1.0927 (3)	0.09199 (18)	0.0633 (7)
H4A	0.8481	1.1446	0.0415	0.095*
O1W	0.3424 (2)	0.7464 (3)	0.69171 (17)	0.0487 (5)
H1W	0.3996	0.7866	0.7687	0.073*
H2W	0.2637	0.7784	0.6716	0.073*
O5	0.0718 (2)	0.7407 (2)	0.05904 (16)	0.0462 (5)
C12	−0.0319 (4)	0.5721 (4)	0.2255 (3)	0.0570 (8)
H12A	−0.1264	0.6015	0.2316	0.086*
H12B	−0.0161	0.5128	0.2835	0.086*
H12C	−0.0653	0.5013	0.1426	0.086*
N3	0.1376 (3)	0.7248 (3)	0.25427 (18)	0.0352 (5)
C11	0.2581 (4)	0.8066 (4)	0.3847 (2)	0.0522 (7)
H11A	0.3625	0.9074	0.3914	0.078*
H11B	0.2971	0.7308	0.4129	0.078*
H11C	0.1933	0.8351	0.4351	0.078*
C10	0.1722 (3)	0.7970 (3)	0.1704 (2)	0.0356 (5)
H10	0.2794	0.8978	0.1949	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0264 (11)	0.0250 (11)	0.0280 (11)	0.0029 (9)	0.0068 (9)	0.0092 (9)
N1	0.0272 (9)	0.0227 (9)	0.0259 (9)	0.0057 (7)	0.0082 (7)	0.0098 (7)
Ni1	0.0196 (3)	0.0191 (3)	0.0217 (3)	0.00424 (18)	0.00625 (17)	0.00652 (17)
C2	0.0216 (10)	0.0230 (10)	0.0262 (11)	0.0024 (8)	0.0062 (8)	0.0055 (9)
N2	0.0256 (9)	0.0274 (10)	0.0254 (9)	−0.0008 (8)	0.0021 (7)	0.0071 (8)
C3	0.0242 (10)	0.0248 (10)	0.0264 (11)	0.0093 (8)	0.0112 (8)	0.0099 (9)
O3W	0.0231 (8)	0.0295 (8)	0.0380 (9)	0.0049 (6)	0.0105 (6)	0.0003 (7)
C4	0.0231 (10)	0.0266 (11)	0.0223 (10)	0.0059 (8)	0.0037 (8)	0.0060 (8)
C5	0.0223 (10)	0.0237 (11)	0.0245 (10)	0.0075 (8)	0.0074 (8)	0.0078 (8)
O1	0.0282 (9)	0.0305 (9)	0.0559 (11)	0.0043 (7)	0.0102 (7)	−0.0071 (8)
C6	0.0252 (10)	0.0278 (11)	0.0258 (11)	0.0073 (9)	0.0082 (8)	0.0098 (9)
O2	0.0233 (9)	0.0324 (9)	0.0833 (15)	0.0073 (7)	0.0126 (8)	0.0002 (9)
C7	0.0283 (11)	0.0312 (11)	0.0217 (10)	0.0069 (9)	0.0037 (8)	0.0072 (9)
C8	0.0295 (11)	0.0328 (12)	0.0266 (12)	0.0063 (9)	0.0078 (9)	0.0113 (10)
C9	0.0220 (10)	0.0249 (11)	0.0249 (11)	0.0059 (9)	0.0050 (8)	0.0095 (9)
O2W	0.0250 (7)	0.0233 (7)	0.0316 (8)	0.0058 (6)	0.0076 (6)	0.0054 (6)
O3	0.0561 (12)	0.0527 (12)	0.0269 (9)	−0.0082 (9)	0.0002 (8)	0.0191 (9)
O4	0.0599 (12)	0.0464 (11)	0.0327 (10)	−0.0161 (9)	−0.0030 (9)	0.0224 (9)
O1W	0.0396 (10)	0.0590 (12)	0.0390 (10)	0.0258 (9)	0.0087 (8)	−0.0036 (9)
O5	0.0409 (10)	0.0468 (10)	0.0272 (9)	0.0019 (8)	0.0025 (7)	0.0156 (8)
C12	0.0560 (17)	0.0591 (18)	0.0607 (19)	0.0195 (14)	0.0312 (15)	0.0326 (15)
N3	0.0421 (11)	0.0367 (11)	0.0260 (10)	0.0184 (9)	0.0101 (9)	0.0103 (9)
C11	0.078 (2)	0.0531 (17)	0.0285 (13)	0.0379 (16)	0.0077 (13)	0.0140 (12)
C10	0.0363 (12)	0.0301 (12)	0.0302 (12)	0.0083 (10)	0.0065 (10)	0.0104 (10)

Geometric parameters (Å, º) top

C1—N1	1.317 (3)	C6—C7	1.386 (3)
C1—N2	1.344 (3)	C6—C8	1.492 (3)
C1—H1	0.9300	O2—C9	1.236 (3)
N1—C3	1.397 (3)	C7—H7	0.9300
N1—Ni1	2.1014 (18)	C8—O3	1.209 (3)
Ni1—O2W	2.0501 (14)	C8—O4	1.293 (3)
Ni1—O2Wⁱ	2.0501 (14)	O2W—H3W	0.8401
Ni1—O3Wⁱ	2.0773 (13)	O2W—H4W	0.8400
Ni1—O3W	2.0773 (13)	O4—H4A	0.8200
Ni1—N1ⁱ	2.1014 (18)	O1W—H1W	0.8408
C2—C7	1.379 (3)	O1W—H2W	0.8405
C2—N2	1.390 (3)	O5—C10	1.252 (3)
C2—C3	1.401 (3)	C12—N3	1.454 (4)
N2—H2	0.8600	C12—H12A	0.9600
C3—C4	1.391 (3)	C12—H12B	0.9600
O3W—H6W	0.8402	C12—H12C	0.9600
O3W—H5W	0.8394	N3—C10	1.298 (3)
C4—C5	1.391 (3)	N3—C11	1.470 (3)
C4—H4	0.9300	C11—H11A	0.9600
C5—C6	1.424 (3)	C11—H11B	0.9600
C5—C9	1.522 (3)	C11—H11C	0.9600
O1—C9	1.240 (3)	C10—H10	0.9300

N1—C1—N2	113.71 (18)	C4—C5—C9	115.96 (18)
N1—C1—H1	123.1	C6—C5—C9	123.63 (19)
N2—C1—H1	123.1	C7—C6—C5	120.7 (2)
C1—N1—C3	104.99 (18)	C7—C6—C8	115.74 (19)
C1—N1—Ni1	123.63 (15)	C5—C6—C8	123.59 (19)
C3—N1—Ni1	131.30 (15)	C2—C7—C6	117.85 (19)
O2W—Ni1—O2Wⁱ	180.0	C2—C7—H7	121.1
O2W—Ni1—O3Wⁱ	91.85 (6)	C6—C7—H7	121.1
O2Wⁱ—Ni1—O3Wⁱ	88.15 (6)	O3—C8—O4	122.2 (2)
O2W—Ni1—O3W	88.15 (6)	O3—C8—C6	122.5 (2)
O2Wⁱ—Ni1—O3W	91.85 (6)	O4—C8—C6	115.3 (2)
O3Wⁱ—Ni1—O3W	180.0	O2—C9—O1	125.6 (2)
O2W—Ni1—N1ⁱ	90.06 (7)	O2—C9—C5	116.7 (2)
O2Wⁱ—Ni1—N1ⁱ	89.94 (7)	O1—C9—C5	117.58 (18)
O3Wⁱ—Ni1—N1ⁱ	90.14 (7)	Ni1—O2W—H3W	109.0
O3W—Ni1—N1ⁱ	89.86 (7)	Ni1—O2W—H4W	117.7
O2W—Ni1—N1	89.94 (7)	H3W—O2W—H4W	110.9
O2Wⁱ—Ni1—N1	90.06 (7)	C8—O4—H4A	109.5
O3Wⁱ—Ni1—N1	89.86 (7)	H1W—O1W—H2W	111.4
O3W—Ni1—N1	90.14 (7)	N3—C12—H12A	109.5
N1ⁱ—Ni1—N1	180.0	N3—C12—H12B	109.5
C7—C2—N2	131.9 (2)	H12A—C12—H12B	109.5
C7—C2—C3	122.56 (19)	N3—C12—H12C	109.5
N2—C2—C3	105.48 (19)	H12A—C12—H12C	109.5
C1—N2—C2	106.79 (18)	H12B—C12—H12C	109.5
C1—N2—H2	126.6	C10—N3—C12	121.1 (2)
C2—N2—H2	126.6	C10—N3—C11	120.7 (2)
C4—C3—N1	131.2 (2)	C12—N3—C11	117.8 (2)
C4—C3—C2	119.76 (19)	N3—C11—H11A	109.5
N1—C3—C2	109.02 (19)	N3—C11—H11B	109.5
Ni1—O3W—H6W	126.3	H11A—C11—H11B	109.5
Ni1—O3W—H5W	111.1	N3—C11—H11C	109.5
H6W—O3W—H5W	111.6	H11A—C11—H11C	109.5
C5—C4—C3	118.77 (19)	H11B—C11—H11C	109.5
C5—C4—H4	120.6	O5—C10—N3	124.8 (2)
C3—C4—H4	120.6	O5—C10—H10	117.6
C4—C5—C6	120.39 (19)	N3—C10—H10	117.6

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O1ⁱⁱ	0.84	1.86	2.693 (3)	173
O1W—H1W···O3ⁱⁱⁱ	0.84	2.00	2.801 (3)	160
O4—H4A···O5^iv	0.82	1.78	2.585 (3)	167
O2W—H4W···O2^v	0.84	1.79	2.624 (3)	176
O2W—H3W···O1Wⁱ	0.84	1.92	2.741 (2)	166
O3W—H5W···O1Wⁱ	0.84	2.06	2.810 (3)	148
O3W—H6W···O1^vi	0.84	1.81	2.634 (3)	169
N2—H2···O5^vii	0.86	1.98	2.779 (3)	155

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

Experimental details

Crystal data
Chemical formula	[Ni(C₉H₅N₂O₄)₂(H₂O)₄]·2C₃H₇NO·2H₂O
M_r	723.30
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.5327 (17), 9.1387 (18), 11.624 (2)
α, β, γ (°)	100.80 (3), 103.03 (3), 114.04 (3)
V (Å³)	765.7 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.27 × 0.18 × 0.17

Data collection
Diffractometer	Rigaku/MSC Mercury CCD diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.830, 0.888
No. of measured, independent and observed [I > 2σ(I)] reflections	6116, 2737, 2613
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.137, 1.20
No. of reflections	2737
No. of parameters	217
No. of restraints	9
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.32

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976), SHELXL9 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O1ⁱ	0.84	1.86	2.693 (3)	172.6
O1W—H1W···O3ⁱⁱ	0.84	2.00	2.801 (3)	159.7
O4—H4A···O5ⁱⁱⁱ	0.82	1.78	2.585 (3)	166.8
O2W—H4W···O2^iv	0.84	1.79	2.624 (3)	175.8
O2W—H3W···O1W^v	0.84	1.92	2.741 (2)	166.3
O3W—H5W···O1W^v	0.84	2.06	2.810 (3)	147.9
O3W—H6W···O1^vi	0.84	1.81	2.634 (3)	168.9
N2—H2···O5^vii	0.86	1.98	2.779 (3)	155.0

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

Acknowledgements

The authors acknowledge Guang Dong Ocean University for supporting this work.

References

Gao, Q., Gao, W.-H., Zhang, C.-Y. & Xie, Y.-B. (2008). Acta Cryst. E64, m928. Web of Science CrossRef IUCr Journals Google Scholar
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Song, W.-D., Wang, H., Li, S.-J., Qin, P.-W. & Hu, S.-W. (2009). Acta Cryst. E65, m702. Web of Science CSD CrossRef IUCr Journals Google Scholar

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