Aqua­bis(1H-imidazole-κN3)bis­(4-methyl­benzoato)-κO;κO,O′-nickel(II)

Song, W.-D.; Fan, R.-Z.; Wu, H.-M.

doi:10.1107/S1600536808009471

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m648

doi:10.1107/S1600536808009471

Open

access

Aquabis(1H-imidazole-κN³)bis(4-methylbenzoato)-κO;κO,O′-nickel(II)

Wen-Dong Song,^a ^* Run-Zhen Fan ^a and Hong-Mian Wu ^b

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

(Received 4 April 2008; accepted 7 April 2008; online 10 April 2008)

In the mononuclear title compound, [Ni(C₈H₇O₂)₂(C₃H₄N₂)₂(H₂O)], the Ni^II atom is coordinated by three carboxylate O atoms (from a bidentate 4-methylbenzoate ligand and a monodentate 4-methylbenzoate ligand), two N atoms (from two imidazole ligands) and a water molecule in an octahedral geometry. Intermolecular O—H⋯O hydrogen-bonding interactions lead to infinite chains, which are further self-assembled into a supramolecular network through intermolecular N—H⋯O hydrogen-bonding interactions and π–π stacking [centroid–centroid distance = 3.717 (2) Å].

Related literature

For related literature, see: Song et al. (2007 ).

Experimental

Crystal data

[Ni(C₈H₇O₂)₂(C₃H₄N₂)₂(H₂O)]
M_r = 483.16
Monoclinic, P 2₁ /n
a = 18.9456 (12) Å
b = 5.8755 (4) Å
c = 20.3209 (14) Å
β = 101.813 (4)°
V = 2214.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.92 mm⁻¹
T = 296 (2) K
0.30 × 0.26 × 0.25 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.770, T_max = 0.803
20580 measured reflections
3776 independent reflections
2815 reflections with I > 2σ(I)
R_int = 0.077

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.171
S = 1.07
3776 reflections
297 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.02 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O3ⁱ	0.826 (10)	2.31 (4)	2.782 (4)	116 (4)
O1W—H1W⋯O2ⁱ	0.826 (10)	2.21 (3)	2.772 (4)	126 (3)
N2—H2⋯O2ⁱⁱ	0.86	1.96	2.816 (5)	175
N4—H22⋯O4ⁱⁱⁱ	0.86	2.02	2.865 (4)	167
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+2; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009471/ng2442sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009471/ng2442Isup2.hkl

checkCIF report

Comment top

In the structural investigation of 4-methylbenzate complexes, it has been found that the 4-methylbenzoic acid functions as a multidentate ligand [Song et al. (2007)], with versatile binding and coordination modes. In this paper, we report the crystal structure of the title compound, (I), a new Ni complex obtained by the reaction of 4-methylbenzoic acid, imidazole and nickel chloride in alkaline aqueous solution.

As illustrated in Figure 1, the Ni^II atom exists in a disordered octahedral environment, defined by three carboxyl O atoms from one bisdentate 4-methylbenzate ligand and one monodentate 4-methylbenzate ligand, two N atoms from two imidazole ligands and one water molecule. Intermolecular O—H···O hydrogen bonding interactions (Table 1) form infinite chains involving the coordinating water molecule as donors and O atoms of 4-methylbenzate ligands as acceptors, which are further self-assembled into a supramolecular network through intermolecular N—H···O hydrogen bonding interactions and π-π stacking interactions of neighboring complexes, with a centroid-centroid distance of 3.717 (2) Å. (Fig. 2).

Related literature top

For related literature, see: Song et al. (2007).

Experimental top

A mixture of nickel chloride(1 mmol), 4-methylbenzoic acid (1 mmol), imidazole(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: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing the atomic numbering scheme. Non-H atoms are shown as 30% probability displacement ellipsoids.
	Fig. 2. The packing of structure (I).

Aquabis(1H-imidazole-κN³)bis(4-methylbenzoato)-κO;κO,O'-nickel(II) top

Crystal data top

[Ni(C₈H₇O₂)₂(C₃H₄N₂)₂(H₂O)]	F(000) = 1008
M_r = 483.16	D_x = 1.449 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3600 reflections
a = 18.9456 (12) Å	θ = 1.4–28°
b = 5.8755 (4) Å	µ = 0.92 mm⁻¹
c = 20.3209 (14) Å	T = 296 K
β = 101.813 (4)°	Block, blue
V = 2214.1 (3) Å³	0.30 × 0.26 × 0.25 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	3776 independent reflections
Radiation source: fine-focus sealed tube	2815 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ϕ and ω scans	θ_max = 25.2°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
T_min = 0.770, T_max = 0.803	k = −7→7
20580 measured reflections	l = −22→21

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.1064P)² + 0.0659P] where P = (F_o² + 2F_c²)/3
3776 reflections	(Δ/σ)_max = 0.001
297 parameters	Δρ_max = 1.02 e Å⁻³
3 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

[Ni(C₈H₇O₂)₂(C₃H₄N₂)₂(H₂O)]	V = 2214.1 (3) Å³
M_r = 483.16	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 18.9456 (12) Å	µ = 0.92 mm⁻¹
b = 5.8755 (4) Å	T = 296 K
c = 20.3209 (14) Å	0.30 × 0.26 × 0.25 mm
β = 101.813 (4)°

Data collection top

Bruker APEXII area-detector diffractometer	3776 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2815 reflections with I > 2σ(I)
T_min = 0.770, T_max = 0.803	R_int = 0.077
20580 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	3 restraints
wR(F²) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 1.02 e Å⁻³
3776 reflections	Δρ_min = −0.71 e Å⁻³
297 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	0.68032 (18)	0.0732 (7)	0.9997 (2)	0.0328 (10)
C2	0.72717 (19)	0.1141 (7)	1.0678 (2)	0.0318 (10)
C3	0.7618 (2)	0.3198 (8)	1.0827 (2)	0.0434 (12)
H3	0.7552	0.4352	1.0507	0.052*
C4	0.8066 (2)	0.3558 (9)	1.1451 (3)	0.0515 (13)
H4	0.8302	0.4949	1.1538	0.062*
C5	0.8171 (2)	0.1911 (9)	1.1943 (3)	0.0450 (12)
C6	0.7816 (2)	−0.0143 (9)	1.1796 (3)	0.0532 (13)
H6	0.7875	−0.1286	1.2119	0.064*
C7	0.7377 (2)	−0.0515 (8)	1.1177 (3)	0.0473 (12)
H7	0.7144	−0.1910	1.1090	0.057*
C8	0.8676 (3)	0.2326 (11)	1.2602 (3)	0.0676 (17)
H8A	0.9136	0.1655	1.2593	0.101*
H8B	0.8482	0.1655	1.2957	0.101*
H8C	0.8733	0.3935	1.2677	0.101*
C9	0.56235 (18)	0.1063 (7)	0.7571 (2)	0.0291 (9)
C10	0.51866 (17)	0.0039 (6)	0.6958 (2)	0.0282 (9)
C11	0.5069 (2)	0.1198 (8)	0.6345 (2)	0.0402 (11)
H11	0.5271	0.2633	0.6325	0.048*
C12	0.4665 (2)	0.0269 (8)	0.5775 (2)	0.0463 (12)
H12	0.4593	0.1088	0.5375	0.056*
C13	0.4360 (2)	−0.1874 (8)	0.5782 (3)	0.0442 (12)
C14	0.4474 (2)	−0.3059 (8)	0.6384 (3)	0.0406 (12)
H14	0.4271	−0.4496	0.6398	0.049*
C15	0.4884 (2)	−0.2135 (7)	0.6964 (2)	0.0351 (11)
H15	0.4960	−0.2964	0.7362	0.042*
C16	0.3904 (3)	−0.2924 (10)	0.5148 (3)	0.0693 (17)
H16A	0.4187	−0.3031	0.4807	0.104*
H16B	0.3490	−0.1985	0.4989	0.104*
H16C	0.3750	−0.4417	0.5249	0.104*
C17	0.49535 (19)	0.5721 (7)	0.8861 (2)	0.0373 (11)
H17	0.5079	0.7042	0.8660	0.045*
C18	0.4381 (2)	0.5510 (8)	0.9164 (2)	0.0433 (12)
H18	0.4047	0.6627	0.9210	0.052*
C19	0.4959 (2)	0.2304 (8)	0.9211 (3)	0.0411 (12)
H19	0.5083	0.0787	0.9301	0.049*
C20	0.7912 (2)	0.2900 (8)	0.8792 (3)	0.0495 (14)
H20	0.7947	0.3948	0.9140	0.059*
C21	0.7474 (2)	0.0663 (7)	0.7991 (2)	0.0420 (11)
H21	0.7152	−0.0160	0.7671	0.050*
N4	0.81940 (17)	0.0528 (6)	0.8074 (2)	0.0467 (10)
H22	0.8430	−0.0306	0.7846	0.056*
N1	0.53185 (15)	0.3705 (6)	0.88955 (18)	0.0333 (8)
N2	0.43972 (17)	0.3329 (7)	0.93841 (19)	0.0413 (10)
H2	0.4098	0.2716	0.9598	0.050*
N3	0.72811 (16)	0.2084 (5)	0.84118 (19)	0.0322 (9)
C22	0.8477 (2)	0.1935 (9)	0.8579 (3)	0.0499 (14)
H4A	0.8964	0.2199	0.8749	0.060*
Ni1	0.62851 (2)	0.29313 (8)	0.86285 (3)	0.0263 (2)
O1	0.67349 (15)	0.2409 (5)	0.95998 (16)	0.0380 (8)
O2	0.65064 (15)	−0.1153 (5)	0.98695 (15)	0.0437 (8)
O3	0.57902 (13)	−0.0107 (4)	0.80995 (15)	0.0338 (7)
O4	0.58228 (13)	0.3134 (4)	0.75769 (15)	0.0300 (7)
O1W	0.66137 (13)	0.6312 (5)	0.87438 (15)	0.0344 (7)
H1W	0.6334 (14)	0.721 (6)	0.887 (2)	0.052*
H2W	0.7005 (9)	0.663 (7)	0.896 (2)	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0320 (19)	0.036 (2)	0.034 (3)	0.0060 (16)	0.0155 (18)	−0.002 (2)
C2	0.0314 (18)	0.038 (2)	0.027 (3)	0.0003 (17)	0.0100 (17)	0.001 (2)
C3	0.049 (2)	0.042 (3)	0.036 (3)	−0.0022 (19)	0.002 (2)	0.009 (2)
C4	0.047 (2)	0.053 (3)	0.050 (4)	−0.008 (2)	0.001 (2)	−0.005 (3)
C5	0.035 (2)	0.069 (3)	0.029 (3)	0.005 (2)	0.0035 (19)	0.002 (3)
C6	0.054 (3)	0.068 (3)	0.035 (3)	0.002 (2)	0.001 (2)	0.021 (3)
C7	0.048 (2)	0.047 (3)	0.046 (3)	−0.007 (2)	0.006 (2)	0.004 (2)
C8	0.050 (3)	0.107 (5)	0.043 (4)	0.002 (3)	0.001 (3)	0.001 (3)
C9	0.0326 (18)	0.026 (2)	0.031 (3)	0.0049 (16)	0.0122 (17)	0.001 (2)
C10	0.0306 (18)	0.030 (2)	0.026 (3)	0.0001 (15)	0.0104 (16)	0.0001 (19)
C11	0.046 (2)	0.034 (2)	0.041 (3)	−0.0007 (19)	0.011 (2)	−0.002 (2)
C12	0.057 (3)	0.048 (3)	0.032 (3)	0.003 (2)	0.005 (2)	0.004 (2)
C13	0.036 (2)	0.055 (3)	0.042 (3)	−0.0048 (19)	0.008 (2)	−0.012 (3)
C14	0.038 (2)	0.040 (3)	0.044 (4)	−0.0082 (17)	0.008 (2)	−0.008 (2)
C15	0.039 (2)	0.030 (2)	0.038 (3)	−0.0015 (16)	0.0107 (19)	−0.001 (2)
C16	0.070 (3)	0.079 (4)	0.057 (5)	−0.020 (3)	0.008 (3)	−0.025 (3)
C17	0.036 (2)	0.034 (2)	0.044 (3)	−0.0018 (16)	0.0125 (18)	−0.007 (2)
C18	0.036 (2)	0.052 (3)	0.045 (3)	0.0025 (19)	0.014 (2)	−0.013 (2)
C19	0.040 (2)	0.042 (3)	0.043 (3)	−0.0010 (18)	0.010 (2)	0.000 (2)
C20	0.034 (2)	0.060 (3)	0.056 (4)	−0.0034 (19)	0.013 (2)	−0.016 (3)
C21	0.043 (2)	0.036 (2)	0.049 (3)	0.0004 (18)	0.015 (2)	−0.008 (2)
N4	0.0425 (19)	0.045 (2)	0.059 (3)	0.0097 (16)	0.0251 (18)	−0.005 (2)
N1	0.0318 (16)	0.0358 (19)	0.035 (2)	−0.0025 (14)	0.0123 (14)	0.0007 (17)
N2	0.0344 (17)	0.058 (3)	0.037 (3)	−0.0090 (16)	0.0194 (16)	−0.006 (2)
N3	0.0329 (16)	0.0297 (18)	0.036 (3)	0.0001 (13)	0.0130 (15)	−0.0062 (17)
C22	0.034 (2)	0.064 (3)	0.055 (4)	0.000 (2)	0.016 (2)	−0.001 (3)
Ni1	0.0288 (3)	0.0243 (3)	0.0276 (4)	0.00023 (17)	0.0098 (2)	0.0002 (2)
O1	0.0404 (15)	0.0427 (18)	0.030 (2)	0.0005 (12)	0.0042 (13)	0.0050 (14)
O2	0.0580 (17)	0.0408 (18)	0.035 (2)	−0.0158 (15)	0.0168 (14)	−0.0062 (16)
O3	0.0400 (14)	0.0276 (15)	0.032 (2)	−0.0014 (11)	0.0030 (12)	0.0030 (14)
O4	0.0374 (14)	0.0249 (15)	0.0286 (19)	−0.0026 (11)	0.0090 (12)	0.0007 (13)
O1W	0.0316 (13)	0.0292 (15)	0.044 (2)	−0.0014 (12)	0.0124 (13)	−0.0067 (14)

Geometric parameters (Å, º) top

C1—O2	1.245 (5)	C15—H15	0.9300
C1—O1	1.264 (5)	C16—H16A	0.9600
C1—C2	1.503 (6)	C16—H16B	0.9600
C2—C3	1.379 (6)	C16—H16C	0.9600
C2—C7	1.389 (6)	C17—C18	1.359 (6)
C3—C4	1.391 (6)	C17—N1	1.366 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.376 (7)	C18—N2	1.356 (6)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.384 (7)	C19—N1	1.315 (5)
C5—C8	1.497 (7)	C19—N2	1.333 (5)
C6—C7	1.376 (6)	C19—H19	0.9300
C6—H6	0.9300	C20—C22	1.359 (6)
C7—H7	0.9300	C20—N3	1.370 (5)
C8—H8A	0.9600	C20—H20	0.9300
C8—H8B	0.9600	C21—N3	1.300 (5)
C8—H8C	0.9600	C21—N4	1.342 (5)
C9—O3	1.260 (5)	C21—H21	0.9300
C9—O4	1.274 (5)	N4—C22	1.341 (6)
C9—C10	1.475 (6)	N4—H22	0.8600
C10—C11	1.396 (6)	N1—Ni1	2.065 (3)
C10—C15	1.401 (5)	N2—H2	0.8600
C11—C12	1.365 (6)	N3—Ni1	2.084 (3)
C11—H11	0.9300	C22—H4A	0.9300
C12—C13	1.387 (6)	Ni1—O1	2.007 (3)
C12—H12	0.9300	Ni1—O1W	2.081 (3)
C13—C14	1.385 (7)	Ni1—O4	2.140 (3)
C13—C16	1.526 (7)	Ni1—O3	2.193 (3)
C14—C15	1.383 (6)	O1W—H1W	0.826 (10)
C14—H14	0.9300	O1W—H2W	0.805 (10)

O2—C1—O1	125.3 (4)	H16B—C16—H16C	109.5
O2—C1—C2	119.4 (4)	C18—C17—N1	109.9 (4)
O1—C1—C2	115.3 (4)	C18—C17—H17	125.1
C3—C2—C7	117.6 (4)	N1—C17—H17	125.1
C3—C2—C1	120.4 (4)	N2—C18—C17	105.6 (4)
C7—C2—C1	121.9 (4)	N2—C18—H18	127.2
C2—C3—C4	120.5 (4)	C17—C18—H18	127.2
C2—C3—H3	119.8	N1—C19—N2	111.5 (4)
C4—C3—H3	119.8	N1—C19—H19	124.2
C5—C4—C3	121.7 (5)	N2—C19—H19	124.2
C5—C4—H4	119.1	C22—C20—N3	109.1 (4)
C3—C4—H4	119.1	C22—C20—H20	125.4
C4—C5—C6	117.7 (4)	N3—C20—H20	125.4
C4—C5—C8	120.3 (5)	N3—C21—N4	111.7 (4)
C6—C5—C8	121.9 (5)	N3—C21—H21	124.1
C7—C6—C5	120.8 (5)	N4—C21—H21	124.1
C7—C6—H6	119.6	C22—N4—C21	107.3 (4)
C5—C6—H6	119.6	C22—N4—H22	126.4
C6—C7—C2	121.7 (4)	C21—N4—H22	126.4
C6—C7—H7	119.2	C19—N1—C17	105.1 (3)
C2—C7—H7	119.2	C19—N1—Ni1	124.4 (3)
C5—C8—H8A	109.5	C17—N1—Ni1	130.1 (3)
C5—C8—H8B	109.5	C19—N2—C18	107.8 (4)
H8A—C8—H8B	109.5	C19—N2—H2	126.1
C5—C8—H8C	109.5	C18—N2—H2	126.1
H8A—C8—H8C	109.5	C21—N3—C20	105.4 (3)
H8B—C8—H8C	109.5	C21—N3—Ni1	132.9 (3)
O3—C9—O4	119.4 (4)	C20—N3—Ni1	121.3 (3)
O3—C9—C10	119.8 (4)	N4—C22—C20	106.5 (4)
O4—C9—C10	120.8 (4)	N4—C22—H4A	126.8
C11—C10—C15	117.5 (4)	C20—C22—H4A	126.8
C11—C10—C9	120.9 (4)	O1—Ni1—N1	89.78 (13)
C15—C10—C9	121.6 (4)	O1—Ni1—O1W	88.76 (12)
C12—C11—C10	121.4 (4)	N1—Ni1—O1W	91.21 (12)
C12—C11—H11	119.3	O1—Ni1—N3	87.18 (13)
C10—C11—H11	119.3	N1—Ni1—N3	176.89 (14)
C11—C12—C13	121.1 (5)	O1W—Ni1—N3	89.37 (11)
C11—C12—H12	119.4	O1—Ni1—O4	174.26 (11)
C13—C12—H12	119.4	N1—Ni1—O4	92.66 (12)
C14—C13—C12	118.4 (4)	O1W—Ni1—O4	96.38 (11)
C14—C13—C16	120.1 (5)	N3—Ni1—O4	90.32 (12)
C12—C13—C16	121.5 (5)	O1—Ni1—O3	114.23 (12)
C15—C14—C13	120.9 (4)	N1—Ni1—O3	89.70 (12)
C15—C14—H14	119.5	O1W—Ni1—O3	157.00 (12)
C13—C14—H14	119.5	N3—Ni1—O3	90.96 (11)
C14—C15—C10	120.6 (4)	O4—Ni1—O3	60.62 (10)
C14—C15—H15	119.7	C1—O1—Ni1	135.7 (3)
C10—C15—H15	119.7	C9—O3—Ni1	88.9 (2)
C13—C16—H16A	109.5	C9—O4—Ni1	90.9 (2)
C13—C16—H16B	109.5	Ni1—O1W—H1W	116 (3)
H16A—C16—H16B	109.5	Ni1—O1W—H2W	120 (3)
C13—C16—H16C	109.5	H1W—O1W—H2W	104.8 (17)
H16A—C16—H16C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O3ⁱ	0.83 (1)	2.31 (4)	2.782 (4)	116 (4)
O1W—H1W···O2ⁱ	0.83 (1)	2.21 (3)	2.772 (4)	126 (3)
N2—H2···O2ⁱⁱ	0.86	1.96	2.816 (5)	175
N4—H22···O4ⁱⁱⁱ	0.86	2.02	2.865 (4)	167

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z+2; (iii) −x+3/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₇O₂)₂(C₃H₄N₂)₂(H₂O)]
M_r	483.16
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	18.9456 (12), 5.8755 (4), 20.3209 (14)
β (°)	101.813 (4)
V (Å³)	2214.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.92
Crystal size (mm)	0.30 × 0.26 × 0.25

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.770, 0.803
No. of measured, independent and observed [I > 2σ(I)] reflections	20580, 3776, 2815
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.171, 1.07
No. of reflections	3776
No. of parameters	297
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.02, −0.71

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O3ⁱ	0.826 (10)	2.31 (4)	2.782 (4)	116 (4)
O1W—H1W···O2ⁱ	0.826 (10)	2.21 (3)	2.772 (4)	126 (3)
N2—H2···O2ⁱⁱ	0.86	1.96	2.816 (5)	174.6
N4—H22···O4ⁱⁱⁱ	0.86	2.02	2.865 (4)	167.1

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y, −z+2; (iii) −x+3/2, y−1/2, −z+3/2.

Acknowledgements

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

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, W.-D., Gu, C.-S., Hao, X.-M. & Liu, J.-W. (2007). Acta Cryst. E63, m1023–m1024. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar