Tetra­aqua­bis­(1H-benzimidazole-5,6-di­carboxyl­ato-κN3)cobalt(II) dimethyl­formamide disolvate dihydrate

Wang, H.; Song, W.-D.; Li, S.-J.; Miao, D.-L.; Liu, J.

doi:10.1107/S1600536809043177

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1423

https://doi.org/10.1107/S1600536809043177

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Tetraaquabis(1H-benzimidazole-5,6-dicarboxylato-κN³)cobalt(II) dimethylformamide disolvate dihydrate

Hao Wang,^a Wen-Dong Song,^b ^* Shi-Jie Li,^a Dong-Liang Miao ^a and Jin Liu ^a

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

(Received 19 October 2009; accepted 20 October 2009; online 23 October 2009)

In the mononuclear title compound, [Co(C₉H₄N₂O₄)₂(H₂O)₄]·2C₃H₇NO·2H₂O, the Co^II atom, which lies on a center of inversion, is coordinated by four water molecules and two N atoms from two two symmetry-related 1H-benzimidazole-5,6-dicarboxylate ligands in a distorted octahedral geometry. The packing is governed by intermolecular O—H⋯O and N—H⋯O hydrogen-bonding interactions.

Related literature

For 1H-benzimidazole-5,6-dicarboxylate complexes, see: Song et al. (2009a ,b ,c ).

Experimental

Crystal data

[Co(C₉H₅N₂O₄)₂(H₂O)₄]·2C₃H₇NO·2H₂O
M_r = 723.52
Triclinic, $[P \overline 1]$
a = 8.5612 (17) Å
b = 9.1475 (18) Å
c = 11.642 (2) Å
α = 100.82 (3)°
β = 102.98 (3)°
γ = 114.11 (3)°
V = 769.9 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.64 mm⁻¹
T = 293 K
0.30 × 0.24 × 0.21 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.831, T_max = 0.877
6161 measured reflections
2751 independent reflections
2594 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.127
S = 0.96
2751 reflections
219 parameters
10 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O5ⁱ	0.839 (10)	1.750 (11)	2.588 (3)	177 (5)
O3W—H6W⋯O1ⁱⁱ	0.84	1.98	2.800 (3)	165
O3W—H5W⋯O3ⁱⁱⁱ	0.84	1.85	2.686 (3)	179
O2W—H3W⋯O3^iv	0.84	1.80	2.636 (3)	174
O2W—H4W⋯O3W	0.84	2.06	2.811 (3)	148
O1W—H1W⋯O4^iv	0.84	1.79	2.624 (3)	170
O1W—H2W⋯O3W^v	0.84	1.94	2.749 (3)	161
N1—H1⋯O5ⁱⁱ	0.86	1.98	2.782 (3)	154
N1—H1⋯O5ⁱⁱ	0.86	1.98	2.782 (3)	154
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x, -y+1, -z; (iii) x, y-1, z; (iv) -x+1, -y+2, -z+1; (v) -x, -y+1, -z+1.

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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809043177/ng2669sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043177/ng2669Isup2.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 based on this idea a series of coordination polymers fomed by this ligand have been reported by us: Pentaaqua(1H-benzimidazole-5,6- dicarboxylato-kN³)cobalt(II)pentahydrate (Song et al., 2009b), Pentaaqua(1H-benzimidazole-5,6-dicarboxylato-κN³)nickel(II)pentahydrate (Song et al., 2009c), catena-Poly[[diaqua(1,10-phenanthroline-k²N,N') nickel(II)]-µ-1H-benzimidazole-5,6-dicarboxylato-k²N³:O⁶] (Song et al., 2009a).In the present paper, we synthesized a novel coordination complex [Co(C₉H₄N₂O₄)₂(H₂O)₄].2H₂O.2C₃H₇NO.

As shown in Figure 1, the Co^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 O1w, O2w, O1wⁱ and O2wⁱ atoms, while N1 and N1ⁱ occupy the axial position (symmetry codes: i = -x, 1 - y, 1 - z). The solvent (water and dimethylformamide) molecules are also present in the asymmetic unit. Inter/intramolecular O—H···O and N—H···O hydrogen bonds form a three-dimensional supramolecular network making the structure more stable(Fig 2).The hydrogen bonds are in the normal range(Table 1).

Related literature top

For 1H-benzimidazole-5,6-dicarboxylate complexes, see: Song et al. (2009a,b,c).

Experimental top

A C₃H₇NO solution (20 mL)containing Co(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 a few weeks, then the red crystals were obtained.

Structure description top

For 1H-benzimidazole-5,6-dicarboxylate complexes, see: Song et al. (2009a,b,c).

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: SHELXL97 (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) -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(1H-benzimidazole-5,6-dicarboxylato- κN³)cobalt(II) dimethylformamide disolvate dihydrate top

Crystal data top

[Co(C₉H₅N₂O₄)₂(H₂O)₄]·2C₃H₇NO·2H₂O	Z = 1
M_r = 723.52	F(000) = 377
Triclinic, P1	D_x = 1.561 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5612 (17) Å	Cell parameters from 3420 reflections
b = 9.1475 (18) Å	θ = 3.3–27.4°
c = 11.642 (2) Å	µ = 0.64 mm⁻¹
α = 100.82 (3)°	T = 293 K
β = 102.98 (3)°	Block, red
γ = 114.11 (3)°	0.30 × 0.24 × 0.21 mm
V = 769.9 (3) Å³

Data collection top

Rigaku/MSC Mercury CCD diffractometer	2751 independent reflections
Radiation source: fine-focus sealed tube	2594 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 = 0.831, T_max = 0.877	k = −10→10
6161 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.0795P)² + 1.194P] where P = (F_o² + 2F_c²)/3
2751 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.58 e Å⁻³
10 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Co(C₉H₅N₂O₄)₂(H₂O)₄]·2C₃H₇NO·2H₂O	γ = 114.11 (3)°
M_r = 723.52	V = 769.9 (3) Å³
Triclinic, P1	Z = 1
a = 8.5612 (17) Å	Mo Kα radiation
b = 9.1475 (18) Å	µ = 0.64 mm⁻¹
c = 11.642 (2) Å	T = 293 K
α = 100.82 (3)°	0.30 × 0.24 × 0.21 mm
β = 102.98 (3)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	2751 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	2594 reflections with I > 2σ(I)
T_min = 0.831, T_max = 0.877	R_int = 0.020
6161 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	10 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.58 e Å⁻³
2751 reflections	Δρ_min = −0.44 e Å⁻³
219 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	0.1417 (4)	0.8422 (3)	0.1200 (2)	0.0279 (6)
C2	0.2484 (3)	0.8904 (3)	0.2467 (2)	0.0247 (5)
C3	0.1906 (3)	0.7887 (3)	0.3191 (2)	0.0269 (5)
H3	0.2595	0.8201	0.4020	0.032*
C4	0.0277 (3)	0.6389 (3)	0.2654 (2)	0.0248 (5)
C5	−0.0742 (3)	0.5940 (3)	0.1405 (2)	0.0272 (6)
C6	−0.0194 (4)	0.6932 (4)	0.0667 (2)	0.0309 (6)
H6	−0.0888	0.6606	−0.0163	0.037*
C7	0.1921 (4)	0.9449 (4)	0.0363 (3)	0.0324 (6)
C8	0.4297 (3)	1.0478 (3)	0.3103 (2)	0.0263 (5)
C9	−0.2117 (4)	0.4034 (3)	0.2225 (3)	0.0310 (6)
H9	−0.2984	0.3064	0.2299	0.037*
C10	0.6732 (4)	0.7964 (4)	0.1713 (3)	0.0344 (6)
H10	0.7801	0.8972	0.1955	0.041*
N3	0.6382 (3)	0.7242 (3)	0.2550 (2)	0.0340 (5)
Co1	0.0000	0.5000	0.5000	0.02238 (18)
N1	−0.2262 (3)	0.4426 (3)	0.1168 (2)	0.0315 (5)
H1	−0.3137	0.3846	0.0473	0.038*
N2	−0.0630 (3)	0.5150 (3)	0.3148 (2)	0.0282 (5)
C12	0.4674 (5)	0.5710 (5)	0.2251 (4)	0.0552 (9)
H3A	0.3742	0.6008	0.2330	0.083*
H3B	0.4829	0.5094	0.2812	0.083*
H3C	0.4330	0.5021	0.1414	0.083*
C11	0.7568 (6)	0.8059 (5)	0.3848 (3)	0.0547 (9)
H4A	0.8640	0.9036	0.3911	0.082*
H4B	0.7907	0.7283	0.4145	0.082*
H4C	0.6937	0.8393	0.4340	0.082*
O1	0.1079 (3)	0.8972 (3)	−0.0726 (2)	0.0582 (7)
O2	0.3337 (4)	1.0933 (3)	0.0904 (2)	0.0635 (8)
O3	0.4308 (3)	1.1767 (3)	0.3708 (2)	0.0458 (6)
O4	0.5660 (3)	1.0359 (3)	0.3035 (3)	0.0524 (6)
O5	0.5725 (3)	0.7391 (3)	0.06005 (19)	0.0457 (6)
O1W	0.0884 (2)	0.7574 (2)	0.57397 (17)	0.0300 (4)
H2W	0.0296	0.7784	0.6176	0.045*
H1W	0.2007	0.8133	0.6126	0.045*
O2W	0.2619 (3)	0.5455 (2)	0.50191 (19)	0.0360 (5)
H4W	0.2576	0.4881	0.4347	0.054*
H3W	0.3630	0.6321	0.5381	0.054*
O3W	0.1590 (3)	0.2539 (3)	0.3083 (2)	0.0498 (6)
H5W	0.2452	0.2312	0.3275	0.075*
H6W	0.0905	0.2004	0.2343	0.075*
H2	0.367 (6)	1.146 (5)	0.041 (3)	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0271 (13)	0.0262 (13)	0.0258 (13)	0.0076 (11)	0.0094 (10)	0.0090 (10)
C2	0.0231 (12)	0.0223 (12)	0.0259 (13)	0.0076 (10)	0.0088 (10)	0.0076 (10)
C3	0.0258 (13)	0.0260 (13)	0.0217 (12)	0.0073 (11)	0.0052 (10)	0.0071 (10)
C4	0.0247 (12)	0.0238 (12)	0.0245 (12)	0.0089 (10)	0.0098 (10)	0.0089 (10)
C5	0.0248 (13)	0.0230 (13)	0.0260 (13)	0.0052 (11)	0.0080 (10)	0.0062 (10)
C6	0.0303 (14)	0.0302 (14)	0.0224 (13)	0.0067 (12)	0.0060 (11)	0.0082 (11)
C7	0.0322 (14)	0.0304 (14)	0.0262 (14)	0.0071 (12)	0.0081 (11)	0.0111 (11)
C8	0.0232 (13)	0.0248 (13)	0.0257 (13)	0.0066 (11)	0.0064 (10)	0.0101 (11)
C9	0.0277 (14)	0.0244 (13)	0.0306 (14)	0.0026 (11)	0.0088 (11)	0.0103 (11)
C10	0.0334 (15)	0.0294 (14)	0.0290 (14)	0.0074 (12)	0.0047 (12)	0.0088 (11)
N3	0.0404 (13)	0.0350 (13)	0.0270 (12)	0.0174 (11)	0.0105 (10)	0.0122 (10)
Co1	0.0203 (3)	0.0186 (3)	0.0219 (3)	0.0040 (2)	0.00591 (19)	0.00645 (19)
N1	0.0243 (11)	0.0260 (12)	0.0229 (11)	−0.0027 (9)	0.0002 (9)	0.0055 (9)
N2	0.0271 (11)	0.0238 (11)	0.0262 (11)	0.0046 (9)	0.0083 (9)	0.0097 (9)
C12	0.052 (2)	0.057 (2)	0.060 (2)	0.0169 (18)	0.0275 (18)	0.0332 (18)
C11	0.085 (3)	0.055 (2)	0.0270 (16)	0.041 (2)	0.0084 (16)	0.0138 (15)
O1	0.0560 (15)	0.0498 (14)	0.0286 (11)	−0.0072 (11)	−0.0002 (10)	0.0191 (10)
O2	0.0580 (15)	0.0463 (14)	0.0325 (12)	−0.0183 (12)	−0.0036 (11)	0.0210 (11)
O3	0.0293 (11)	0.0302 (11)	0.0569 (14)	0.0051 (9)	0.0109 (10)	−0.0062 (10)
O4	0.0218 (10)	0.0340 (12)	0.0823 (18)	0.0077 (9)	0.0093 (11)	−0.0002 (11)
O5	0.0399 (12)	0.0433 (12)	0.0270 (11)	−0.0014 (10)	0.0014 (9)	0.0144 (9)
O1W	0.0238 (9)	0.0245 (9)	0.0318 (10)	0.0058 (8)	0.0057 (8)	0.0051 (8)
O2W	0.0250 (10)	0.0296 (10)	0.0399 (11)	0.0049 (8)	0.0114 (8)	0.0004 (8)
O3W	0.0428 (13)	0.0590 (15)	0.0395 (12)	0.0271 (12)	0.0088 (10)	−0.0033 (11)

Geometric parameters (Å, º) top

C1—C6	1.381 (4)	N3—C12	1.462 (4)
C1—C2	1.424 (4)	N3—C11	1.463 (4)
C1—C7	1.489 (4)	Co1—O1W	2.086 (2)
C2—C3	1.387 (4)	Co1—O1Wⁱ	2.086 (2)
C2—C8	1.513 (4)	Co1—O2Wⁱ	2.1007 (19)
C3—C4	1.393 (4)	Co1—O2W	2.1007 (19)
C3—H3	0.9300	Co1—N2	2.146 (2)
C4—N2	1.395 (3)	Co1—N2ⁱ	2.146 (2)
C4—C5	1.398 (4)	N1—H1	0.8600
C5—C6	1.382 (4)	C12—H3A	0.9600
C5—N1	1.382 (3)	C12—H3B	0.9600
C6—H6	0.9300	C12—H3C	0.9600
C7—O1	1.201 (4)	C11—H4A	0.9600
C7—O2	1.304 (4)	C11—H4B	0.9600
C8—O4	1.234 (3)	C11—H4C	0.9600
C8—O3	1.250 (3)	O2—H2	0.839 (10)
C9—N2	1.315 (4)	O1W—H2W	0.8400
C9—N1	1.338 (4)	O1W—H1W	0.8400
C9—H9	0.9300	O2W—H4W	0.8399
C10—O5	1.253 (3)	O2W—H3W	0.8399
C10—N3	1.299 (4)	O3W—H5W	0.8400
C10—H10	0.9300	O3W—H6W	0.8399

C6—C1—C2	120.8 (2)	O1Wⁱ—Co1—O2W	88.64 (8)
C6—C1—C7	115.4 (2)	O2Wⁱ—Co1—O2W	180.0
C2—C1—C7	123.8 (2)	O1W—Co1—N2	90.82 (9)
C3—C2—C1	120.3 (2)	O1Wⁱ—Co1—N2	89.18 (9)
C3—C2—C8	115.8 (2)	O2Wⁱ—Co1—N2	90.29 (9)
C1—C2—C8	123.9 (2)	O2W—Co1—N2	89.71 (9)
C2—C3—C4	118.9 (2)	O1W—Co1—N2ⁱ	89.18 (9)
C2—C3—H3	120.6	O1Wⁱ—Co1—N2ⁱ	90.82 (9)
C4—C3—H3	120.6	O2Wⁱ—Co1—N2ⁱ	89.71 (9)
C3—C4—N2	131.3 (2)	O2W—Co1—N2ⁱ	90.29 (9)
C3—C4—C5	119.7 (2)	N2—Co1—N2ⁱ	179.999 (1)
N2—C4—C5	108.9 (2)	C9—N1—C5	107.1 (2)
C6—C5—N1	132.1 (2)	C9—N1—H1	126.5
C6—C5—C4	122.4 (2)	C5—N1—H1	126.5
N1—C5—C4	105.5 (2)	C9—N2—C4	104.9 (2)
C1—C6—C5	117.9 (2)	C9—N2—Co1	124.00 (18)
C1—C6—H6	121.0	C4—N2—Co1	130.98 (18)
C5—C6—H6	121.0	N3—C12—H3A	109.5
O1—C7—O2	121.9 (3)	N3—C12—H3B	109.5
O1—C7—C1	123.1 (3)	H3A—C12—H3B	109.5
O2—C7—C1	115.0 (2)	N3—C12—H3C	109.5
O4—C8—O3	125.2 (3)	H3A—C12—H3C	109.5
O4—C8—C2	117.0 (2)	H3B—C12—H3C	109.5
O3—C8—C2	117.7 (2)	N3—C11—H4A	109.5
N2—C9—N1	113.6 (2)	N3—C11—H4B	109.5
N2—C9—H9	123.2	H4A—C11—H4B	109.5
N1—C9—H9	123.2	N3—C11—H4C	109.5
O5—C10—N3	124.3 (3)	H4A—C11—H4C	109.5
O5—C10—H10	117.8	H4B—C11—H4C	109.5
N3—C10—H10	117.8	C7—O2—H2	114 (3)
C10—N3—C12	120.6 (3)	Co1—O1W—H2W	113.1
C10—N3—C11	120.7 (3)	Co1—O1W—H1W	113.3
C12—N3—C11	118.2 (3)	H2W—O1W—H1W	110.9
O1W—Co1—O1Wⁱ	180.0	Co1—O2W—H4W	110.8
O1W—Co1—O2Wⁱ	88.64 (8)	Co1—O2W—H3W	130.9
O1Wⁱ—Co1—O2Wⁱ	91.36 (8)	H4W—O2W—H3W	112.2
O1W—Co1—O2W	91.36 (8)	H5W—O3W—H6W	112.2

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱⁱ	0.84 (1)	1.75 (1)	2.588 (3)	177 (5)
O3W—H6W···O1ⁱⁱⁱ	0.84	1.98	2.800 (3)	165
O3W—H5W···O3^iv	0.84	1.85	2.686 (3)	179
O2W—H3W···O3^v	0.84	1.80	2.636 (3)	174
O2W—H4W···O3W	0.84	2.06	2.811 (3)	148
O1W—H1W···O4^v	0.84	1.79	2.624 (3)	170
O1W—H2W···O3Wⁱ	0.84	1.94	2.749 (3)	161
N1—H1···O5ⁱⁱⁱ	0.86	1.98	2.782 (3)	154
N1—H1···O5ⁱⁱⁱ	0.86	1.98	2.782 (3)	154

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

Experimental details

Crystal data
Chemical formula	[Co(C₉H₅N₂O₄)₂(H₂O)₄]·2C₃H₇NO·2H₂O
M_r	723.52
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.5612 (17), 9.1475 (18), 11.642 (2)
α, β, γ (°)	100.82 (3), 102.98 (3), 114.11 (3)
V (Å³)	769.9 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.30 × 0.24 × 0.21

Data collection
Diffractometer	Rigaku/MSC Mercury CCD
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.831, 0.877
No. of measured, independent and observed [I > 2σ(I)] reflections	6161, 2751, 2594
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.127, 0.96
No. of reflections	2751
No. of parameters	219
No. of restraints	10
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.44

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱ	0.839 (10)	1.750 (11)	2.588 (3)	177 (5)
O3W—H6W···O1ⁱⁱ	0.84	1.98	2.800 (3)	165.1
O3W—H5W···O3ⁱⁱⁱ	0.84	1.85	2.686 (3)	178.5
O2W—H3W···O3^iv	0.84	1.80	2.636 (3)	173.5
O2W—H4W···O3W	0.84	2.06	2.811 (3)	148.3
O1W—H1W···O4^iv	0.84	1.79	2.624 (3)	170.0
O1W—H2W···O3W^v	0.84	1.94	2.749 (3)	160.7
N1—H1···O5ⁱⁱ	0.86	1.98	2.782 (3)	154.3
N1—H1···O5ⁱⁱ	0.86	1.98	2.782 (3)	154.3

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

Acknowledgements

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

References

Jacobson, R. (1998). REQAB. MSC, The Woodlands, Texas, USA. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, W.-D., Wang, H., Hu, S.-W., Qin, P.-W. & Li, S.-J. (2009a). Acta Cryst. E65, m701. Web of Science CSD CrossRef IUCr Journals Google Scholar
Song, W.-D., Wang, H., Li, S.-J., Qin, P.-W. & Hu, S.-W. (2009b). Acta Cryst. E65, m702. Web of Science CSD CrossRef IUCr Journals Google Scholar
Song, W.-D., Wang, H., Qin, P.-W., Li, S.-J. & Hu, S.-W. (2009c). Acta Cryst. E65, m672. Web of Science CSD CrossRef IUCr Journals Google Scholar

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