Poly[[aqua­(μ4-1H-benzimidazole-5,6-dicarboxyl­ato-κ4N3:O5:O5′:O6)(N,N-dimethyl­formamide-κO)cadmium(II)] dihydrate]

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

doi:10.1107/S1600536810003065

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Pages m209-m210

https://doi.org/10.1107/S1600536810003065

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Poly[[aqua(μ₄-1H-benzimidazole-5,6-dicarboxylato-κ⁴N³:O⁵:O^5′:O⁶)(N,N-dimethylformamide-κO)cadmium(II)] dihydrate]

Hao Wang,^a Shi-Jie Li,^a Wen-Dong Song,^b ^* Xiao-Fei Li ^c and Dong-Liang Miao ^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 17 January 2010; accepted 25 January 2010; online 30 January 2010)

In the title compound, {[Cd(C₉H₄N₂O₄)(C₃H₇NO)(H₂O)]·2H₂O}_n, the Cd^II atom is coordinated by one N atom and three O atoms from four different 1H-benzimidazole-5,6-dicarboxylate (Hbidc) ligands, one O atom from one dimethylformamide ligand, and one O atom from a water molecule in a distorted octahedral geometry. The Hbidc ligands connect the Cd atoms into a two-dimensional network parallel to (001). N—H⋯O and O—H⋯O hydrogen bonds involving the water molecules are observed in the crystal structure.

Related literature

For related structures of 1H-benzimidazole-5,6-dicarboxylate complexes, see: Song, Wang, Hu et al. (2009 ); Song, Wang, Li et al. (2009 ); Song, Wang, Qin et al. (2009 ); Wang et al. (2009 ).

Experimental

Crystal data

[Cd(C₉H₄N₂O₄)(C₃H₇NO)(H₂O)]·2H₂O
M_r = 443.69
Triclinic, $[P \overline 1]$
a = 7.7729 (16) Å
b = 9.1648 (18) Å
c = 11.458 (2) Å
α = 102.76 (3)°
β = 97.70 (3)°
γ = 94.96 (3)°
V = 783.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.44 mm⁻¹
T = 293 K
0.29 × 0.25 × 0.21 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.680, T_max = 0.752
6197 measured reflections
2800 independent reflections
1539 reflections with I > 2σ(I)
R_int = 0.121

Refinement

R[F² > 2σ(F²)] = 0.086
wR(F²) = 0.223
S = 1.14
2800 reflections
219 parameters
9 restraints
H-atom parameters constrained
Δρ_max = 2.12 e Å⁻³
Δρ_min = −1.80 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O2ⁱ	0.84	1.92	2.757 (11)	177
O1W—H2W⋯O4ⁱⁱ	0.84	1.85	2.649 (12)	159
O2W—H3W⋯O1W	0.84	2.16	2.888 (9)	145
O2W—H4W⋯O1	0.84	2.00	2.811 (11)	162
O3W—H5W⋯O2ⁱ	0.84	2.11	2.810 (12)	140
O3W—H6W⋯O2Wⁱⁱⁱ	0.84	2.29	2.766 (14)	117
N2—H2⋯O2W^iv	0.86	2.18	2.970 (16)	152
Symmetry codes: (i) x+1, y, z; (ii) -x, -y, -z+1; (iii) -x+1, -y, -z+2; (iv) x, y+1, z.

Data collection: CrystalStructure (Rigaku/MSC, 2002 ); cell refinement: CrystalStructure; data reduction: CrystalStructure; 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/S1600536810003065/hy2275sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810003065/hy2275Isup2.hkl

checkCIF report

Comment top

From the structural point of view, 1H-benzimidazole-5,6-dicarboxylic acid (H₃bidc) possesses two N atoms of imidazole ring and four O atoms of carboxylate groups and might be used as versatile linker in constructing coordination polymers with abundant hydrogen bonds. Based on this idea, a series of coordination polymers fomed by this ligand have been reported by us: catena-poly[[diaqua(1,10-phenanthroline-κ²N,N')nickel(II)]- µ-Hbidc-κ²N³:O⁶] (Song, Wang, Hu et al., 2009), pentaaqua(Hbidc-κN³)cobalt(II) pentahydrate (Song, Wang, Li et al., 2009), pentaaqua(Hbidc-κN³)nickel(II) pentahydrate (Song, Wang, Qin et al., 2009), and tetraaquabis(Hbidc-κN³)cobalt(II) dimethylformamide disolvate dihydrate (Wang et al., 2009). In the present paper, we report the title complex.

As shown in Fig. 1, the Cd^II atom exhibits an octahedral coordination geometry, defined by three O atoms from three different Hbidc ligands, one N atom from another Hbidc ligand, one O atom from a dimethylformamide ligand and one O atom from a water molecule. The equatorial plane is defined by O1W, O10, N1ⁱ and O3ⁱⁱⁱ atoms, while O1 and O4ⁱⁱ occupy the axial positions [symmetry codes: (i) -x, 1-y, 1-z; (ii) 1+x, y, z; (iii) -x, -y, 1-z]. Two solvent water molecules are present in the asymmetic unit. O—H···O and N—H···O hydrogen bonds are observed in the crystal structure with hydrogen-bond geometry in the normal range (Fig. 2 and Table 1).

Related literature top

For related structures of 1H-benzimidazole-5,6-dicarboxylate complexes, see: Song, Wang, Hu et al. (2009); Song, Wang, Li et al. (2009); Song, Wang, Qin et al. (2009); Wang et al. (2009).

Experimental top

A dimethylformamide solution (20 ml) containing CdCl₂(0.1 mmol) and H₃bidc (0.2 mmol) was stirred for a few minutes in air, and then left to stand at room temperature. Colorless crystals were obtained in a few weeks.

Structure description top

For related structures of 1H-benzimidazole-5,6-dicarboxylate complexes, see: Song, Wang, Hu et al. (2009); Song, Wang, Li et al. (2009); Song, Wang, Qin et al. (2009); Wang et al. (2009).

Computing details top

Data collection: CrystalStructure (Rigaku/MSC, 2002); cell refinement: CrystalStructure (Rigaku/MSC, 2002); 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 asymmetric unit of the title compound, showing the 30% probability displacement ellipsoids. [Symmetry codes: (i) -x, 1-y, 1-z; (ii) 1+x, y, z; (iii) -x, -y,1-z.]
	Fig. 2. A view of the crystal packing. Hydrogen bonds are shown as dashed lines.

Poly[[aqua(µ₄-1H-benzimidazole-5,6-dicarboxylato- κ⁴N³:O⁵:O^5':O⁶)(N,N- dimethylformamide-κO)cadmium(II)] dihydrate] top

Crystal data top

[Cd(C₉H₄N₂O₄)(C₃H₇NO)(H₂O)]·2H₂O	Z = 2
M_r = 443.69	F(000) = 444
Triclinic, P1	D_x = 1.881 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7729 (16) Å	Cell parameters from 3441 reflections
b = 9.1648 (18) Å	θ = 3.3–27.4°
c = 11.458 (2) Å	µ = 1.44 mm⁻¹
α = 102.76 (3)°	T = 293 K
β = 97.70 (3)°	Block, colorless
γ = 94.96 (3)°	0.29 × 0.25 × 0.21 mm
V = 783.2 (3) Å³

Data collection top

Rigaku/MSC Mercury CCD diffractometer	2800 independent reflections
Radiation source: fine-focus sealed tube	1539 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.121
ω scans	θ_max = 25.2°, θ_min = 3.3°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −9→7
T_min = 0.680, T_max = 0.752	k = −10→10
6197 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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.223	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0683P)² + 2.7388P] where P = (F_o² + 2F_c²)/3
2800 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 2.12 e Å⁻³
9 restraints	Δρ_min = −1.80 e Å⁻³

Crystal data top

[Cd(C₉H₄N₂O₄)(C₃H₇NO)(H₂O)]·2H₂O	γ = 94.96 (3)°
M_r = 443.69	V = 783.2 (3) Å³
Triclinic, P1	Z = 2
a = 7.7729 (16) Å	Mo Kα radiation
b = 9.1648 (18) Å	µ = 1.44 mm⁻¹
c = 11.458 (2) Å	T = 293 K
α = 102.76 (3)°	0.29 × 0.25 × 0.21 mm
β = 97.70 (3)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	2800 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	1539 reflections with I > 2σ(I)
T_min = 0.680, T_max = 0.752	R_int = 0.121
6197 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.086	9 restraints
wR(F²) = 0.223	H-atom parameters constrained
S = 1.14	Δρ_max = 2.12 e Å⁻³
2800 reflections	Δρ_min = −1.80 e Å⁻³
219 parameters

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

	x	y	z	U_iso*/U_eq
Cd1	0.32811 (14)	0.19007 (13)	0.58926 (9)	0.0427 (4)
O1	0.1397 (12)	0.1778 (11)	0.7248 (7)	0.043 (2)
O2	−0.1244 (11)	0.1608 (11)	0.7803 (8)	0.043 (2)
O1W	0.5202 (9)	0.0812 (8)	0.7112 (7)	0.045 (3)
O10	0.4501 (13)	0.4197 (11)	0.7028 (8)	0.048 (3)
N1	−0.1716 (14)	0.7274 (13)	0.5549 (9)	0.037 (3)
N2	0.0418 (16)	0.7573 (12)	0.7100 (10)	0.046 (3)
H2	0.1247	0.8019	0.7676	0.055*
N3	0.6296 (17)	0.5826 (15)	0.8605 (11)	0.057 (4)
C1	−0.0542 (18)	0.8220 (17)	0.6334 (13)	0.044 (4)
H1	−0.0382	0.9245	0.6362	0.053*
C2	−0.1506 (16)	0.5900 (15)	0.5837 (12)	0.035 (3)
C3	−0.2450 (15)	0.4482 (15)	0.5278 (10)	0.031 (3)
H3	−0.3353	0.4370	0.4633	0.037*
C4	−0.1988 (17)	0.3261 (16)	0.5722 (11)	0.037 (3)
C5	−0.0634 (17)	0.3421 (14)	0.6700 (11)	0.033 (3)
C6	0.0295 (17)	0.4860 (17)	0.7241 (12)	0.045 (4)
H6	0.1203	0.4999	0.7887	0.054*
C7	−0.0192 (16)	0.6032 (16)	0.6778 (10)	0.033 (3)
C8	−0.0144 (18)	0.2164 (15)	0.7258 (12)	0.039 (3)
C11	0.758 (3)	0.606 (2)	0.9664 (14)	0.086 (6)
H11A	0.7649	0.5123	0.9907	0.128*
H11B	0.7250	0.6793	1.0306	0.128*
H11C	0.8693	0.6407	0.9491	0.128*
C12	0.587 (2)	0.713 (2)	0.8183 (16)	0.077 (6)
H12A	0.5613	0.6868	0.7313	0.116*
H12B	0.6835	0.7907	0.8445	0.116*
H12C	0.4859	0.7477	0.8506	0.116*
C10	0.560 (2)	0.4477 (19)	0.7957 (13)	0.054 (4)
H10	0.5975	0.3655	0.8226	0.065*
O3W	0.7681 (13)	0.2252 (9)	1.0089 (11)	0.127 (6)
H5W	0.8465	0.2124	0.9650	0.190*
H6W	0.6998	0.1446	0.9891	0.190*
O2W	0.2935 (7)	0.0032 (12)	0.8739 (9)	0.080 (4)
H3W	0.3906	0.0207	0.8522	0.120*
H4W	0.2273	0.0510	0.8364	0.120*
C9	−0.2912 (17)	0.1756 (17)	0.5120 (11)	0.036 (3)
O3	−0.2155 (12)	0.0562 (10)	0.5048 (7)	0.041 (2)
O4	−0.4532 (9)	0.1698 (8)	0.4625 (7)	0.043 (2)
H1W	0.6279	0.1081	0.7315	0.065*
H2W	0.4982	−0.0084	0.6711	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0451 (7)	0.0367 (7)	0.0457 (6)	−0.0036 (5)	0.0070 (4)	0.0115 (5)
O1	0.040 (6)	0.042 (6)	0.043 (5)	−0.015 (5)	0.005 (4)	0.013 (4)
O2	0.033 (5)	0.041 (6)	0.059 (6)	−0.002 (5)	0.007 (4)	0.024 (5)
O1W	0.040 (5)	0.038 (6)	0.049 (5)	−0.017 (5)	0.006 (4)	0.004 (5)
O10	0.054 (6)	0.044 (7)	0.039 (5)	−0.003 (5)	−0.005 (5)	0.006 (5)
N1	0.035 (6)	0.030 (7)	0.042 (6)	0.000 (6)	0.000 (5)	0.006 (5)
N2	0.056 (8)	0.023 (7)	0.053 (7)	−0.007 (6)	0.011 (6)	0.002 (6)
N3	0.062 (9)	0.034 (8)	0.064 (8)	0.003 (7)	−0.009 (7)	0.004 (7)
C1	0.048 (9)	0.035 (9)	0.064 (9)	0.014 (7)	0.021 (8)	0.031 (8)
C2	0.030 (7)	0.029 (8)	0.057 (8)	0.011 (6)	0.020 (6)	0.020 (7)
C3	0.025 (6)	0.043 (9)	0.023 (6)	−0.010 (6)	0.001 (5)	0.010 (6)
C4	0.035 (8)	0.040 (9)	0.034 (7)	−0.009 (7)	0.003 (6)	0.009 (6)
C5	0.045 (8)	0.022 (7)	0.033 (7)	0.002 (6)	0.006 (6)	0.008 (6)
C6	0.032 (8)	0.055 (10)	0.043 (8)	−0.006 (7)	−0.007 (6)	0.016 (7)
C7	0.029 (7)	0.047 (9)	0.029 (7)	0.016 (7)	0.003 (5)	0.016 (6)
C8	0.041 (9)	0.027 (8)	0.043 (8)	−0.011 (7)	0.010 (6)	−0.002 (6)
C11	0.105 (16)	0.080 (15)	0.052 (10)	0.008 (12)	−0.028 (10)	0.001 (10)
C12	0.083 (14)	0.063 (14)	0.078 (12)	0.011 (11)	0.036 (10)	−0.013 (10)
C10	0.065 (11)	0.049 (11)	0.049 (9)	0.012 (9)	0.009 (8)	0.009 (8)
O3W	0.171 (17)	0.126 (15)	0.085 (10)	−0.006 (12)	0.049 (10)	0.020 (10)
O2W	0.075 (8)	0.090 (10)	0.088 (8)	0.009 (7)	0.027 (7)	0.041 (8)
C9	0.037 (8)	0.044 (9)	0.030 (7)	0.006 (7)	0.008 (6)	0.015 (6)
O3	0.056 (6)	0.028 (6)	0.039 (5)	0.000 (5)	0.011 (4)	0.005 (4)
O4	0.044 (6)	0.037 (6)	0.041 (5)	−0.009 (5)	0.008 (4)	−0.001 (4)

Geometric parameters (Å, º) top

Cd1—N1ⁱ	2.226 (11)	C3—C4	1.382 (19)
Cd1—O10	2.266 (9)	C3—H3	0.9300
Cd1—O1	2.287 (8)	C4—C5	1.404 (18)
Cd1—O3ⁱⁱ	2.314 (9)	C4—C9	1.472 (18)
Cd1—O1W	2.344 (9)	C5—C6	1.414 (18)
Cd1—O4ⁱⁱⁱ	2.373 (7)	C5—C8	1.489 (19)
O1—C8	1.278 (16)	C6—C7	1.359 (19)
O2—C8	1.261 (14)	C6—H6	0.9300
O1W—H1W	0.8380	C11—H11A	0.9600
O1W—H2W	0.8382	C11—H11B	0.9600
O10—C10	1.236 (17)	C11—H11C	0.9600
N1—C1	1.301 (17)	C12—H12A	0.9600
N1—C2	1.388 (17)	C12—H12B	0.9600
N2—C1	1.346 (17)	C12—H12C	0.9600
N2—C7	1.400 (17)	C10—H10	0.9300
N2—H2	0.8600	O3W—H5W	0.8411
N3—C10	1.320 (19)	O3W—H6W	0.8398
N3—C11	1.426 (19)	O2W—H3W	0.8389
N3—C12	1.43 (2)	O2W—H4W	0.8393
C1—H1	0.9300	C9—O3	1.279 (16)
C2—C7	1.359 (18)	C9—O4	1.302 (14)
C2—C3	1.407 (17)

N1ⁱ—Cd1—O10	96.6 (4)	C3—C4—C9	118.6 (11)
N1ⁱ—Cd1—O1	103.1 (4)	C5—C4—C9	119.8 (13)
O10—Cd1—O1	89.6 (3)	C4—C5—C6	119.5 (13)
N1ⁱ—Cd1—O3ⁱⁱ	90.6 (4)	C4—C5—C8	123.9 (12)
O10—Cd1—O3ⁱⁱ	172.6 (3)	C6—C5—C8	116.6 (12)
O1—Cd1—O3ⁱⁱ	86.9 (3)	C7—C6—C5	117.3 (12)
N1ⁱ—Cd1—O1W	169.1 (3)	C7—C6—H6	121.3
O10—Cd1—O1W	88.5 (3)	C5—C6—H6	121.3
O1—Cd1—O1W	86.5 (3)	C6—C7—C2	124.0 (13)
O3ⁱⁱ—Cd1—O1W	84.8 (3)	C6—C7—N2	132.0 (12)
N1ⁱ—Cd1—O4ⁱⁱⁱ	85.9 (3)	C2—C7—N2	103.9 (12)
O10—Cd1—O4ⁱⁱⁱ	93.7 (3)	O2—C8—O1	123.0 (14)
O1—Cd1—O4ⁱⁱⁱ	170.0 (3)	O2—C8—C5	117.4 (13)
O3ⁱⁱ—Cd1—O4ⁱⁱⁱ	88.7 (3)	O1—C8—C5	119.3 (11)
O1W—Cd1—O4ⁱⁱⁱ	84.1 (3)	N3—C11—H11A	109.5
C8—O1—Cd1	130.4 (8)	N3—C11—H11B	109.5
H1W—O1W—H2W	112.2	H11A—C11—H11B	109.5
C10—O10—Cd1	127.5 (11)	N3—C11—H11C	109.5
C1—N1—C2	103.9 (12)	H11A—C11—H11C	109.5
C1—N1—Cd1ⁱ	118.8 (10)	H11B—C11—H11C	109.5
C2—N1—Cd1ⁱ	137.1 (9)	N3—C12—H12A	109.5
C1—N2—C7	106.8 (11)	N3—C12—H12B	109.5
C1—N2—H2	126.6	H12A—C12—H12B	109.5
C7—N2—H2	126.6	N3—C12—H12C	109.5
C10—N3—C11	123.2 (15)	H12A—C12—H12C	109.5
C10—N3—C12	119.1 (14)	H12B—C12—H12C	109.5
C11—N3—C12	117.5 (15)	O10—C10—N3	126.5 (16)
N1—C1—N2	113.5 (13)	O10—C10—H10	116.7
N1—C1—H1	123.2	N3—C10—H10	116.7
N2—C1—H1	123.2	H5W—O3W—H6W	105.9
C7—C2—N1	111.8 (12)	H3W—O2W—H4W	103.7
C7—C2—C3	120.0 (13)	O3—C9—O4	121.1 (12)
N1—C2—C3	128.2 (13)	O3—C9—C4	122.1 (12)
C4—C3—C2	117.7 (11)	O4—C9—C4	116.8 (13)
C4—C3—H3	121.2	C9—O3—Cd1ⁱⁱ	128.7 (8)
C2—C3—H3	121.2	C9—O4—Cd1^iv	118.5 (7)
C3—C4—C5	121.6 (12)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2ⁱⁱⁱ	0.84	1.92	2.757 (11)	177
O1W—H2W···O4ⁱⁱ	0.84	1.85	2.649 (12)	159
O2W—H3W···O1W	0.84	2.16	2.888 (9)	145
O2W—H4W···O1	0.84	2.00	2.811 (11)	162
O3W—H5W···O2ⁱⁱⁱ	0.84	2.11	2.810 (12)	140
O3W—H6W···O2W^v	0.84	2.29	2.766 (14)	117
N2—H2···O2W^vi	0.86	2.18	2.970 (16)	152

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

Experimental details

Crystal data
Chemical formula	[Cd(C₉H₄N₂O₄)(C₃H₇NO)(H₂O)]·2H₂O
M_r	443.69
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.7729 (16), 9.1648 (18), 11.458 (2)
α, β, γ (°)	102.76 (3), 97.70 (3), 94.96 (3)
V (Å³)	783.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.44
Crystal size (mm)	0.29 × 0.25 × 0.21

Data collection
Diffractometer	Rigaku/MSC Mercury CCD
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.680, 0.752
No. of measured, independent and observed [I > 2σ(I)] reflections	6197, 2800, 1539
R_int	0.121
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.086, 0.223, 1.14
No. of reflections	2800
No. of parameters	219
No. of restraints	9
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.12, −1.80

Computer programs: 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
O1W—H1W···O2ⁱ	0.84	1.92	2.757 (11)	177
O1W—H2W···O4ⁱⁱ	0.84	1.85	2.649 (12)	159
O2W—H3W···O1W	0.84	2.16	2.888 (9)	145
O2W—H4W···O1	0.84	2.00	2.811 (11)	162
O3W—H5W···O2ⁱ	0.84	2.11	2.810 (12)	140
O3W—H6W···O2Wⁱⁱⁱ	0.84	2.29	2.766 (14)	117
N2—H2···O2W^iv	0.86	2.18	2.970 (16)	152

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

Acknowledgements

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

References

Jacobson, R. (1998). REQAB. Private communication to the Molecular Structure Corporation, The Woodlands, Texas, USA. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
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