Penta­aqua­(1H-benzimidazole-5,6-dicarboxyl­ato-κN3)nickel(II) penta­hydrate

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

doi:10.1107/S1600536809018704

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page m672

doi:10.1107/S1600536809018704

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Pentaaqua(1H-benzimidazole-5,6-dicarboxylato-κN³)nickel(II) pentahydrate

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

^aCollege of Science, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
^*Correspondence e-mail: songwd60@126.com

(Received 14 May 2009; accepted 18 May 2009; online 23 May 2009)

In the title mononuclear complex, [Ni(C₉H₄N₂O₄)(H₂O)₅]·5H₂O, the Ni^II atom is six-coordinated by one N atom from a 1H-benzimidazole-5,6-dicarboxylate ligand and by five O atoms from five water molecules and displays a distorted octahedral geometry. Intermolecular O—H⋯O hydrogen-bonding interactions among the coordinated water molecules, solvent water molecules and carboxyl O atoms of the organic ligand and additional N—H⋯O hydrogen bonding lead to the formation of a three-dimensional supramolecular network.

Related literature

For background information on 1H-benzimidazole-5,6-dicarboxylate complexes, see: Lo et al. (2007 ); Yao et al. (2008 ).

Experimental

Crystal data

[Ni(C₉H₄N₂O₄)(H₂O)₅]·5H₂O
M_r = 443.01
Triclinic, $[P \overline 1]$
a = 6.8436 (14) Å
b = 11.434 (2) Å
c = 12.344 (3) Å
α = 78.29 (3)°
β = 78.65 (3)°
γ = 74.92 (3)°
V = 902.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.15 mm⁻¹
T = 293 K
0.31 × 0.25 × 0.21 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.725, T_max = 0.793
7176 measured reflections
3228 independent reflections
2851 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.167
S = 1.14
3228 reflections
235 parameters
30 restraints
H-atom parameters constrained
Δρ_max = 1.53 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10W—H20W⋯O1W	0.84	2.00	2.836 (4)	176
O10W—H19W⋯O8Wⁱ	0.84	1.88	2.703 (5)	166
O9W—H17W⋯O3ⁱⁱ	0.84	1.90	2.733 (5)	172
O9W—H18W⋯O10Wⁱⁱⁱ	0.84	1.91	2.720 (5)	163
O8W—H15W⋯O1^iv	0.84	1.95	2.765 (5)	163
O8W—H16W⋯O2	0.84	1.96	2.775 (5)	162
O7W—H13W⋯O8W^v	0.84	1.93	2.754 (5)	165
O7W—H14W⋯O4^v	0.84	1.91	2.734 (5)	169
O6W—H12W⋯O2W^vi	0.84	2.06	2.857 (4)	159
O6W—H11W⋯O4^vii	0.84	1.97	2.808 (4)	174
O5W—H10W⋯O4^viii	0.84	1.96	2.800 (4)	176
O5W—H9W⋯O9Wⁱⁱⁱ	0.84	1.98	2.817 (4)	173
O4W—H8W⋯O9W^v	0.84	1.90	2.736 (5)	173
O4W—H7W⋯O3^ix	0.84	1.94	2.709 (4)	151
O3W—H6W⋯O6W^viii	0.84	1.93	2.761 (4)	172
O3W—H5W⋯O7W^x	0.84	1.93	2.729 (5)	159
O2W—H4W⋯O1^v	0.84	1.80	2.620 (4)	164
O2W—H3W⋯O10W^iv	0.84	1.90	2.734 (5)	175
O1W—H1W⋯O6W^v	0.84	1.96	2.783 (5)	168
O1W—H2W⋯O2^v	0.84	1.79	2.612 (4)	166
N1—H1⋯O7W^xi	0.86	1.97	2.803 (5)	162
Symmetry codes: (i) x-1, y, z; (ii) x, y, z-1; (iii) -x, -y+1, -z+1; (iv) x+1, y, z; (v) -x+1, -y+1, -z+1; (vi) -x+2, -y+1, -z+1; (vii) -x+1, -y+2, -z+1; (viii) x, y-1, z; (ix) x+1, y-1, z; (x) -x+1, -y, -z+1; (xi) x, y, 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: 10.1107/S1600536809018704/zl2208sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018704/zl2208Isup2.hkl

checkCIF report

Comment top

In the structural investigation of 1H-benzimidazole-5,6-dicarboxylate complexes, it has been found that the 1H-benzimidazole-5,6-dicarboxylic acid can function as a multidentate ligand (Lo et al., 2007; Yao et al., 2008), with versatile binding and coordination modes. In this paper, we report the crystal structure of the title compound, a new Ni complex obtained by the reaction of 1H-benzimidazole-5,6-dicarboxylic acid with nickel chloride in an alkaline aqueous solution.

As illustrated in Fig. 1, the Ni^II atom exhibits a slightly distorted octahedral coordination sphere, defined by one N atom from the 1H-benzimidazole-5,6-dicarboxylate ligand and five coordinated water molecules. The five non-bonded solvent water molecules are located in cavities of the three-dimensional framework, allowing them to participate in various O—H···O hydrogen bonds (Table 1) with the coordinated water molecules, non-coordinated water molecules and carboxylate O atoms of the organic ligand. The hydrogen bonds are in the normal range (Table 1, Fig. 2).

Related literature top

For background information on 1H-benzimidazole-5,6-dicarboxylate complexes, see: Lo et al., (2007); Yao et al., (2008).

Experimental top

A mixture of nickel chloride (1 mmol), 1H-benzimidazole-5,6-dicarboxylic acid (1 mmol), NaOH (1.5 mmol) and H₂O (12 ml) was placed in a 23 ml Teflon reactor, which was heated to 433 K for three days and then cooled to room temperature at a rate of 10 K h^-1. The crystals obtained were washed with water and dryed in air.

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. Non-H atoms are shown with 30% probability displacement ellipsoids.
	Fig. 2. A packing view of the title compound. The intermolecular hydrogen bonds are shown as dashed lines.

Pentaaqua(1H-benzimidazole-5,6-dicarboxylato-κN³)nickel(II) pentahydrate top

Crystal data top

[Ni(C₉H₄N₂O₄)(H₂O)₅]·5H₂O	Z = 2
M_r = 443.01	F(000) = 464
Triclinic, P1	D_x = 1.630 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8436 (14) Å	Cell parameters from 3600 reflections
b = 11.434 (2) Å	θ = 1.4–28°
c = 12.344 (3) Å	µ = 1.15 mm⁻¹
α = 78.29 (3)°	T = 293 K
β = 78.65 (3)°	Block, blue
γ = 74.92 (3)°	0.31 × 0.25 × 0.21 mm
V = 902.6 (3) Å³

Data collection top

Rigaku Mercury CCD diffractometer	3228 independent reflections
Radiation source: fine-focus sealed tube	2851 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 25.2°, θ_min = 3.1°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −8→8
T_min = 0.725, T_max = 0.793	k = −13→13
7176 measured reflections	l = −14→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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0905P)² + 1.2897P] where P = (F_o² + 2F_c²)/3
3228 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 1.53 e Å⁻³
30 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

[Ni(C₉H₄N₂O₄)(H₂O)₅]·5H₂O	γ = 74.92 (3)°
M_r = 443.01	V = 902.6 (3) Å³
Triclinic, P1	Z = 2
a = 6.8436 (14) Å	Mo Kα radiation
b = 11.434 (2) Å	µ = 1.15 mm⁻¹
c = 12.344 (3) Å	T = 293 K
α = 78.29 (3)°	0.31 × 0.25 × 0.21 mm
β = 78.65 (3)°

Data collection top

Rigaku Mercury CCD diffractometer	3228 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	2851 reflections with I > 2σ(I)
T_min = 0.725, T_max = 0.793	R_int = 0.048
7176 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	30 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.14	Δρ_max = 1.53 e Å⁻³
3228 reflections	Δρ_min = −0.60 e Å⁻³
235 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	0.3714 (6)	0.5621 (4)	0.7112 (3)	0.0205 (8)
N1	0.3498 (6)	0.3063 (3)	0.9967 (3)	0.0272 (8)
H1	0.3074	0.3078	1.0669	0.033*
Ni1	0.59930 (7)	0.09723 (4)	0.74101 (4)	0.0200 (2)
O1	0.2171 (5)	0.6926 (3)	0.5614 (3)	0.0379 (8)
C2	0.4484 (6)	0.4375 (3)	0.7118 (3)	0.0210 (8)
H2	0.5106	0.4068	0.6460	0.025*
N2	0.4903 (5)	0.2318 (3)	0.8396 (3)	0.0224 (7)
O2	0.5536 (5)	0.6543 (3)	0.5459 (2)	0.0346 (8)
C3	0.4301 (6)	0.3595 (3)	0.8136 (3)	0.0209 (8)
O3	0.0491 (5)	0.7830 (3)	0.8792 (3)	0.0346 (8)
C4	0.3381 (6)	0.4072 (4)	0.9121 (3)	0.0230 (8)
O4	0.3074 (5)	0.8139 (3)	0.7441 (3)	0.0328 (7)
C5	0.2592 (6)	0.5316 (4)	0.9124 (3)	0.0253 (9)
H5	0.1973	0.5617	0.9785	0.030*
C6	0.2755 (6)	0.6096 (4)	0.8113 (3)	0.0222 (8)
C7	0.4385 (7)	0.2068 (4)	0.9496 (3)	0.0258 (9)
H7	0.4618	0.1277	0.9898	0.031*
C8	0.2025 (6)	0.7459 (4)	0.8107 (3)	0.0243 (9)
C9	0.3812 (6)	0.6449 (3)	0.5979 (3)	0.0217 (8)
O1W	0.3920 (4)	0.1803 (3)	0.6302 (2)	0.0284 (7)
H2W	0.4303	0.2272	0.5727	0.043*
H1W	0.3513	0.1237	0.6138	0.043*
O2W	0.8180 (4)	0.1821 (3)	0.6393 (2)	0.0274 (6)
H3W	0.8697	0.2273	0.6656	0.041*
H4W	0.7925	0.2129	0.5744	0.041*
O3W	0.7170 (6)	−0.0427 (3)	0.6518 (3)	0.0463 (10)
H5W	0.7472	−0.1164	0.6823	0.070*
H6W	0.7539	−0.0344	0.5822	0.070*
O4W	0.7928 (5)	0.0082 (3)	0.8549 (3)	0.0313 (7)
H7W	0.8647	−0.0596	0.8391	0.047*
H8W	0.8618	0.0475	0.8765	0.047*
O5W	0.3802 (5)	0.0021 (3)	0.8336 (2)	0.0285 (7)
H9W	0.2734	0.0489	0.8607	0.043*
H10W	0.3518	−0.0525	0.8072	0.043*
O6W	0.8012 (5)	0.9831 (3)	0.4213 (2)	0.0340 (7)
H11W	0.7615	1.0420	0.3717	0.051*
H12W	0.9257	0.9499	0.4049	0.051*
O7W	0.2893 (5)	0.2719 (3)	0.2313 (3)	0.0372 (8)
H14W	0.4128	0.2554	0.2398	0.056*
H13W	0.2201	0.3317	0.2624	0.056*
O8W	0.9187 (5)	0.5590 (3)	0.6314 (3)	0.0431 (8)
H16W	0.8200	0.5777	0.5952	0.065*
H15W	1.0137	0.5932	0.5982	0.065*
O9W	−0.0044 (5)	0.8476 (3)	0.0863 (3)	0.0378 (8)
H18W	0.0184	0.7895	0.1395	0.057*
H17W	0.0075	0.8220	0.0257	0.057*
O10W	0.0100 (5)	0.3191 (3)	0.7221 (3)	0.0406 (8)
H19W	−0.0044	0.3950	0.7006	0.061*
H20W	0.1257	0.2800	0.6958	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0213 (19)	0.021 (2)	0.0181 (18)	−0.0063 (15)	−0.0026 (15)	0.0000 (15)
N1	0.041 (2)	0.0185 (17)	0.0163 (16)	−0.0034 (14)	−0.0012 (15)	0.0021 (13)
Ni1	0.0245 (3)	0.0148 (3)	0.0184 (3)	−0.0027 (2)	−0.0024 (2)	−0.00091 (19)
O1	0.0319 (17)	0.0426 (19)	0.0323 (16)	−0.0088 (14)	−0.0108 (13)	0.0156 (14)
C2	0.025 (2)	0.0178 (19)	0.0179 (18)	−0.0028 (15)	−0.0014 (15)	−0.0019 (14)
N2	0.0285 (18)	0.0143 (16)	0.0211 (16)	−0.0028 (13)	−0.0034 (14)	0.0013 (12)
O2	0.0295 (16)	0.0383 (18)	0.0272 (16)	−0.0074 (13)	−0.0024 (13)	0.0123 (13)
C3	0.0221 (19)	0.0179 (19)	0.0218 (19)	−0.0035 (15)	−0.0035 (15)	−0.0023 (15)
O3	0.0371 (17)	0.0234 (16)	0.0344 (17)	0.0036 (13)	0.0036 (14)	−0.0068 (12)
C4	0.028 (2)	0.021 (2)	0.0189 (19)	−0.0063 (16)	−0.0015 (16)	−0.0002 (14)
O4	0.0382 (18)	0.0188 (15)	0.0391 (17)	−0.0077 (12)	−0.0007 (14)	−0.0031 (12)
C5	0.031 (2)	0.021 (2)	0.0205 (19)	−0.0028 (16)	−0.0002 (16)	−0.0037 (15)
C6	0.023 (2)	0.017 (2)	0.024 (2)	−0.0018 (15)	−0.0034 (16)	−0.0027 (15)
C7	0.035 (2)	0.0179 (19)	0.022 (2)	−0.0049 (16)	−0.0046 (17)	0.0015 (15)
C8	0.030 (2)	0.018 (2)	0.024 (2)	−0.0036 (16)	−0.0074 (17)	−0.0021 (15)
C9	0.030 (2)	0.0166 (19)	0.0192 (19)	−0.0058 (16)	−0.0053 (16)	−0.0015 (14)
O1W	0.0327 (16)	0.0282 (16)	0.0246 (14)	−0.0124 (12)	−0.0063 (12)	0.0039 (11)
O2W	0.0297 (15)	0.0283 (16)	0.0238 (14)	−0.0103 (12)	−0.0053 (12)	0.0023 (11)
O3W	0.081 (3)	0.0219 (16)	0.0287 (17)	−0.0075 (16)	0.0088 (17)	−0.0086 (13)
O4W	0.0315 (16)	0.0221 (15)	0.0396 (17)	0.0020 (12)	−0.0139 (13)	−0.0052 (12)
O5W	0.0327 (16)	0.0227 (15)	0.0292 (15)	−0.0092 (12)	0.0025 (12)	−0.0053 (11)
O6W	0.0355 (18)	0.0310 (17)	0.0306 (16)	−0.0042 (13)	−0.0035 (13)	0.0006 (12)
O7W	0.0381 (18)	0.0401 (19)	0.0320 (17)	−0.0067 (14)	−0.0040 (14)	−0.0067 (14)
O8W	0.0349 (18)	0.039 (2)	0.052 (2)	−0.0080 (15)	−0.0099 (15)	0.0024 (15)
O9W	0.0462 (19)	0.0365 (18)	0.0310 (16)	−0.0061 (15)	−0.0090 (15)	−0.0077 (13)
O10W	0.0358 (18)	0.0334 (18)	0.051 (2)	−0.0075 (14)	−0.0088 (15)	−0.0022 (15)

Geometric parameters (Å, º) top

C1—C2	1.383 (5)	C5—H5	0.9300
C1—C6	1.422 (6)	C6—C8	1.506 (5)
C1—C9	1.522 (5)	C7—H7	0.9300
N1—C7	1.332 (5)	O1W—H2W	0.8400
N1—C4	1.387 (5)	O1W—H1W	0.8400
N1—H1	0.8600	O2W—H3W	0.8400
Ni1—O3W	2.029 (3)	O2W—H4W	0.8400
Ni1—O4W	2.053 (3)	O3W—H5W	0.8400
Ni1—N2	2.052 (3)	O3W—H6W	0.8400
Ni1—O2W	2.069 (3)	O4W—H7W	0.8400
Ni1—O1W	2.078 (3)	O4W—H8W	0.8400
Ni1—O5W	2.099 (3)	O5W—H9W	0.8400
O1—C9	1.242 (5)	O5W—H10W	0.8400
C2—C3	1.390 (5)	O6W—H11W	0.8400
C2—H2	0.9300	O6W—H12W	0.8400
N2—C7	1.325 (5)	O7W—H14W	0.8400
N2—C3	1.398 (5)	O7W—H13W	0.8400
O2—C9	1.247 (5)	O8W—H16W	0.8400
C3—C4	1.400 (6)	O8W—H15W	0.8400
O3—C8	1.250 (5)	O9W—H18W	0.8400
C4—C5	1.384 (6)	O9W—H17W	0.8400
O4—C8	1.263 (5)	O10W—H19W	0.8400
C5—C6	1.383 (5)	O10W—H20W	0.8400

C2—C1—C6	121.3 (3)	C6—C5—H5	121.1
C2—C1—C9	117.1 (3)	C4—C5—H5	121.1
C6—C1—C9	121.5 (3)	C5—C6—C1	120.4 (4)
C7—N1—C4	107.6 (3)	C5—C6—C8	118.6 (3)
C7—N1—H1	126.2	C1—C6—C8	120.9 (3)
C4—N1—H1	126.2	N2—C7—N1	113.3 (3)
O3W—Ni1—O4W	88.73 (14)	N2—C7—H7	123.4
O3W—Ni1—N2	176.19 (13)	N1—C7—H7	123.4
O4W—Ni1—N2	87.52 (13)	O3—C8—O4	124.7 (4)
O3W—Ni1—O2W	86.14 (14)	O3—C8—C6	118.0 (4)
O4W—Ni1—O2W	92.83 (12)	O4—C8—C6	117.1 (3)
N2—Ni1—O2W	94.75 (13)	O1—C9—O2	124.9 (4)
O3W—Ni1—O1W	90.63 (14)	O1—C9—C1	117.3 (3)
O4W—Ni1—O1W	176.58 (11)	O2—C9—C1	117.7 (4)
N2—Ni1—O1W	93.07 (13)	Ni1—O1W—H2W	117.9
O2W—Ni1—O1W	90.49 (11)	Ni1—O1W—H1W	106.6
O3W—Ni1—O5W	89.34 (13)	H2W—O1W—H1W	111.6
O4W—Ni1—O5W	88.84 (13)	Ni1—O2W—H3W	119.4
N2—Ni1—O5W	89.88 (13)	Ni1—O2W—H4W	115.2
O2W—Ni1—O5W	175.15 (11)	H3W—O2W—H4W	111.6
O1W—Ni1—O5W	87.79 (12)	Ni1—O3W—H5W	122.7
C1—C2—C3	118.0 (4)	Ni1—O3W—H6W	125.1
C1—C2—H2	121.0	H5W—O3W—H6W	111.9
C3—C2—H2	121.0	Ni1—O4W—H7W	113.0
C7—N2—C3	104.9 (3)	Ni1—O4W—H8W	119.4
C7—N2—Ni1	122.5 (3)	H7W—O4W—H8W	111.4
C3—N2—Ni1	132.1 (3)	Ni1—O5W—H9W	112.7
C2—C3—N2	130.8 (4)	Ni1—O5W—H10W	119.8
C2—C3—C4	120.3 (4)	H9W—O5W—H10W	111.1
N2—C3—C4	108.9 (3)	H11W—O6W—H12W	111.6
N1—C4—C5	132.6 (4)	H14W—O7W—H13W	111.7
N1—C4—C3	105.3 (3)	H16W—O8W—H15W	111.6
C5—C4—C3	122.2 (4)	H18W—O9W—H17W	111.7
C6—C5—C4	117.8 (4)	H19W—O10W—H20W	111.4

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10W—H20W···O1W	0.84	2.00	2.836 (4)	176
O10W—H19W···O8Wⁱ	0.84	1.88	2.703 (5)	166
O9W—H17W···O3ⁱⁱ	0.84	1.90	2.733 (5)	172
O9W—H18W···O10Wⁱⁱⁱ	0.84	1.91	2.720 (5)	163
O8W—H15W···O1^iv	0.84	1.95	2.765 (5)	163
O8W—H16W···O2	0.84	1.96	2.775 (5)	162
O7W—H13W···O8W^v	0.84	1.93	2.754 (5)	165
O7W—H14W···O4^v	0.84	1.91	2.734 (5)	169
O6W—H12W···O2W^vi	0.84	2.06	2.857 (4)	159
O6W—H11W···O4^vii	0.84	1.97	2.808 (4)	174
O5W—H10W···O4^viii	0.84	1.96	2.800 (4)	176
O5W—H9W···O9Wⁱⁱⁱ	0.84	1.98	2.817 (4)	173
O4W—H8W···O9W^v	0.84	1.90	2.736 (5)	173
O4W—H7W···O3^ix	0.84	1.94	2.709 (4)	151
O3W—H6W···O6W^viii	0.84	1.93	2.761 (4)	172
O3W—H5W···O7W^x	0.84	1.93	2.729 (5)	159
O2W—H4W···O1^v	0.84	1.80	2.620 (4)	164
O2W—H3W···O10W^iv	0.84	1.90	2.734 (5)	175
O1W—H1W···O6W^v	0.84	1.96	2.783 (5)	168
O1W—H2W···O2^v	0.84	1.79	2.612 (4)	166
N1—H1···O7W^xi	0.86	1.97	2.803 (5)	162

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

Experimental details

Crystal data
Chemical formula	[Ni(C₉H₄N₂O₄)(H₂O)₅]·5H₂O
M_r	443.01
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.8436 (14), 11.434 (2), 12.344 (3)
α, β, γ (°)	78.29 (3), 78.65 (3), 74.92 (3)
V (Å³)	902.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.15
Crystal size (mm)	0.31 × 0.25 × 0.21

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.725, 0.793
No. of measured, independent and observed [I > 2σ(I)] reflections	7176, 3228, 2851
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.167, 1.14
No. of reflections	3228
No. of parameters	235
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.53, −0.60

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
O10W—H20W···O1W	0.84	2.00	2.836 (4)	176.4
O10W—H19W···O8Wⁱ	0.84	1.88	2.703 (5)	165.9
O9W—H17W···O3ⁱⁱ	0.84	1.90	2.733 (5)	172.2
O9W—H18W···O10Wⁱⁱⁱ	0.84	1.91	2.720 (5)	163.0
O8W—H15W···O1^iv	0.84	1.95	2.765 (5)	163.3
O8W—H16W···O2	0.84	1.96	2.775 (5)	162.3
O7W—H13W···O8W^v	0.84	1.93	2.754 (5)	165.2
O7W—H14W···O4^v	0.84	1.91	2.734 (5)	168.7
O6W—H12W···O2W^vi	0.84	2.06	2.857 (4)	158.9
O6W—H11W···O4^vii	0.84	1.97	2.808 (4)	174.3
O5W—H10W···O4^viii	0.84	1.96	2.800 (4)	175.7
O5W—H9W···O9Wⁱⁱⁱ	0.84	1.98	2.817 (4)	173.3
O4W—H8W···O9W^v	0.84	1.90	2.736 (5)	173.4
O4W—H7W···O3^ix	0.84	1.94	2.709 (4)	150.9
O3W—H6W···O6W^viii	0.84	1.93	2.761 (4)	172.2
O3W—H5W···O7W^x	0.84	1.93	2.729 (5)	159.2
O2W—H4W···O1^v	0.84	1.80	2.620 (4)	163.5
O2W—H3W···O10W^iv	0.84	1.90	2.734 (5)	174.7
O1W—H1W···O6W^v	0.84	1.96	2.783 (5)	167.6
O1W—H2W···O2^v	0.84	1.79	2.612 (4)	165.8
N1—H1···O7W^xi	0.86	1.97	2.803 (5)	162.2

Acknowledgements

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

References

Jacobson, R. (1998). REQAB. 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
Lo, Y.-L., Wang, W.-C., Lee, G.-A. & Liu, Y.-H. (2007). Acta Cryst. E63, m2657–m2658. Web of Science CSD CrossRef IUCr Journals 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
Yao, Y. L., Che, Y. X. & Zheng, J. M. (2008). Cryst. Growth Des. 8, 2299–2306. Web of Science CSD CrossRef CAS Google Scholar