Bis(1H-benzimidazole-κN3)bis­[2-(naphthalen-1-yl)acetato-κ2O,O′]nickel(II) monohydrate

Yin, F.-J.; Han, L.-J.; Hong, Z.; Xu, X.-Y.; Ren, L.

doi:10.1107/S1600536812010021

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page m416

doi:10.1107/S1600536812010021

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Bis(1H-benzimidazole-κN³)bis[2-(naphthalen-1-yl)acetato-κ²O,O′]nickel(II) monohydrate

Fu-Jun Yin,^a ^* Li-Jun Han,^b Zhao Hong,^c Xing-You Xu ^d and Li Ren ^e

^aJiangsu Marine Resources Development Research Institute, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^bDepartment of Mathematics and Science, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^cDepartment of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, ^dHuaiyin Insititute of Technology, Huaiyin 223003, People's Republic of China, and ^eQian'an College, Hebei United University, Tangshan 063009, People's Republic of China
^*Correspondence e-mail: yfj1999@126.com

(Received 26 February 2012; accepted 7 March 2012; online 14 March 2012)

In the title compound, [Ni(C₁₂H₉O₂)₂(C₇H₆N₂)₂]·H₂O, The Ni^II cation is located on a twofold rotation axis and is six-coordinated in a distorted NiN₂O₄ octahedral geometry. The asymmetric unit consists of a nickel(II) ion, one 2-(naphthalen-1-yl)acetate anion, a neutral benzotriazole ligand and one half of a lattice water molecule. The crystal packing is stabilized by O—H⋯O and N—H⋯O hydrogen bonds. The title compound is isotypic with its Cd^II analogue.

Related literature

For the crystal structures of related 2-(naphthalen-1-yl)acetate complexes, see: Yin et al. (2011a ,b ); Liu et al. (2007 ); Yang et al. (2008 ); Tang et al. (2006 ); Ji et al. (2011 ). For the isotypic Cd^II complex, see: Duan et al. (2007 ).

Experimental

Crystal data

[Ni(C₁₂H₉O₂)₂(C₇H₆N₂)₂]·H₂O
M_r = 683.37
Monoclinic, C 2/c
a = 11.573 (4) Å
b = 19.991 (7) Å
c = 14.290 (5) Å
β = 105.903 (4)°
V = 3179.5 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.66 mm⁻¹
T = 298 K
0.10 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.952, T_max = 0.952
11840 measured reflections
2807 independent reflections
1849 reflections with I > 2σ(I)
R_int = 0.083

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.122
S = 0.99
2807 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O4	0.90 (8)	2.24 (8)	2.988 (6)	141 (8)
N2—H2⋯O4ⁱ	0.86	2.00	2.791 (4)	152
Symmetry code: (i) -x+1, -y+1, -z+1.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812010021/bg2448sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010021/bg2448Isup2.hkl

checkCIF report

Comment top

In recent years particular interest has been devoted to the 1-naphthylacetate ligand in coordination chemistry due to its ability to form metal complexes (Yin et al., 2011a, 2011b; Liu et al.,2007; Yang et al., 2008; Tang et al.,2006 ; Ji et al., 2011). The crystal structure of the title compound was determined as part of an ongoing study of the properties of nickel complexes containing imidazole ligands. In the title mononuclear metal complex, the asymmetric unit consists of a nickel cation, one 2-(naphthalen-1-yl)acetate anion,a benzotriazole ligand, and half of a lattic water molecule. The Ni^II cation is located on a two fold rotation axis and is six coordinated by two N from two benzotriazoles and four O atoms from two different 2-(naphthalen-1-yl)acetate anions, displaying a distorted NiN2O4 octahedral geometry, with Ni-O bond lengths in the range 2.056 (2)-2.288 (2)Å; the Ni-N bond length is 2.020 (3)Å. The crystal packing is stabilized by intermolecular N—H···O hydrogen bonding (Fig. 2) interactions which give rise to a one-dimensional chain structure. An isotypic cadmium(II) structure has been reported previously (Duan et al., 2007).

Related literature top

For the crystal structures of related 2-(naphthalen-1-yl)acetate complexes, see: Yin et al. (2011a,b); Liu et al. (2007); Yang et al. (2008); Tang et al. (2006); Ji et al. (2011). For the isotypic Cd^II complex, see: Duan et al. (2007).

Experimental top

The title compound was synthesized by the reaction ofNi(NO₃)₂.6H₂O, (87.24 mg, 0.3 mmol), 1-naphthylacetic acid(93 mg, 0.5 mmol), benzotriazole (35.4mg, 0.3 mmol) and NaOH (20 mg, 0.5 mmol) in 16 mL of a water-ethanol (2:1) mixture under solvothermal conditions. The mixture was homogenized and transferred into a sealed Teflon-lined solvothermal bomb (volume: 25 ml) and heated to 160°C for three days. After cooling colorless the crystals of the title compound were obtained, which were washed with distilled water and absolute ethanol.

Structure description top

For the crystal structures of related 2-(naphthalen-1-yl)acetate complexes, see: Yin et al. (2011a,b); Liu et al. (2007); Yang et al. (2008); Tang et al. (2006); Ji et al. (2011). For the isotypic Cd^II complex, see: Duan et al. (2007).

Computing details top

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

Figures top

	Fig. 1. Molecule and the asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 30% probability level.Hydrogenbonding is shown as dashed lines[Symmetry code: (A) 1-x, y, 1.5-z].
	Fig. 2. Part of the one-dimensional chain structure of (I) formed by N—H···O hydrogen bonds (dashed lines)along [001].

Bis(1H-benzimidazole-κN³)bis[2-(naphthalen-1-yl)acetato-κ²O,O']nickel(II) monohydrate top

Crystal data top

[Ni(C₁₂H₉O₂)₂(C₇H₆N₂)₂]·H₂O	F(000) = 1424
M_r = 683.37	D_x = 1.428 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1368 reflections
a = 11.573 (4) Å	θ = 3.5–23.4°
b = 19.991 (7) Å	µ = 0.66 mm⁻¹
c = 14.290 (5) Å	T = 298 K
β = 105.903 (4)°	Block, colourless
V = 3179.5 (19) Å³	0.10 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2807 independent reflections
Radiation source: fine-focus sealed tube	1849 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.083
φ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.952, T_max = 0.952	k = −23→23
11840 measured reflections	l = −16→16

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0569P)²] where P = (F_o² + 2F_c²)/3
2807 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Ni(C₁₂H₉O₂)₂(C₇H₆N₂)₂]·H₂O	V = 3179.5 (19) Å³
M_r = 683.37	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 11.573 (4) Å	µ = 0.66 mm⁻¹
b = 19.991 (7) Å	T = 298 K
c = 14.290 (5) Å	0.10 × 0.10 × 0.10 mm
β = 105.903 (4)°

Data collection top

Bruker APEXII CCD diffractometer	2807 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1849 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.952	R_int = 0.083
11840 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.41 e Å⁻³
2807 reflections	Δρ_min = −0.43 e Å⁻³
221 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.6876 (3)	0.58948 (19)	0.7714 (2)	0.0396 (9)
C2	0.8061 (3)	0.6268 (2)	0.7974 (3)	0.0527 (10)
H2A	0.8067	0.6572	0.8505	0.063*
H2B	0.8701	0.5946	0.8214	0.063*
C3	0.8350 (3)	0.6664 (2)	0.7174 (3)	0.0460 (9)
C4	0.8408 (3)	0.7344 (2)	0.7213 (3)	0.0585 (11)
H4	0.8252	0.7564	0.7738	0.070*
C5	0.8696 (4)	0.7721 (2)	0.6480 (4)	0.0679 (13)
H5	0.8750	0.8184	0.6533	0.081*
C6	0.8898 (4)	0.7412 (2)	0.5694 (3)	0.0661 (13)
H6	0.9074	0.7667	0.5206	0.079*
C7	0.8844 (3)	0.6714 (2)	0.5609 (3)	0.0507 (10)
C8	0.8573 (3)	0.63328 (19)	0.6355 (3)	0.0433 (9)
C9	0.8534 (3)	0.5631 (2)	0.6255 (3)	0.0525 (11)
H9	0.8374	0.5371	0.6744	0.063*
C10	0.8724 (4)	0.5324 (2)	0.5464 (4)	0.0665 (13)
H10	0.8690	0.4860	0.5416	0.080*
C11	0.8969 (4)	0.5702 (3)	0.4727 (4)	0.0741 (14)
H11	0.9087	0.5489	0.4182	0.089*
C12	0.9039 (3)	0.6382 (3)	0.4795 (3)	0.0666 (13)
H12	0.9216	0.6629	0.4301	0.080*
C13	0.4383 (3)	0.44910 (18)	0.5645 (2)	0.0421 (9)
H13	0.3634	0.4697	0.5500	0.050*
C14	0.5879 (3)	0.38798 (17)	0.5476 (3)	0.0428 (9)
C15	0.6185 (3)	0.41847 (17)	0.6388 (2)	0.0370 (8)
C16	0.7297 (3)	0.40796 (19)	0.7041 (3)	0.0515 (10)
H16	0.7507	0.4278	0.7653	0.062*
C17	0.8083 (4)	0.3663 (2)	0.6737 (4)	0.0638 (12)
H17	0.8842	0.3582	0.7154	0.077*
C18	0.7766 (4)	0.3365 (2)	0.5830 (4)	0.0684 (13)
H18	0.8319	0.3087	0.5658	0.082*
C19	0.6675 (4)	0.34618 (19)	0.5176 (3)	0.0556 (11)
H19	0.6472	0.3261	0.4565	0.067*
N1	0.5211 (2)	0.45750 (13)	0.64759 (19)	0.0380 (7)
N2	0.4725 (3)	0.40802 (14)	0.5028 (2)	0.0434 (8)
H2	0.4300	0.3964	0.4458	0.052*
Ni1	0.5000	0.52246 (3)	0.7500	0.0369 (2)
O2	0.6755 (2)	0.54170 (12)	0.82476 (17)	0.0469 (7)
O4	0.6028 (2)	0.60642 (12)	0.69919 (17)	0.0441 (6)
O1W	0.5000	0.7341 (3)	0.7500	0.163 (4)
H1A	0.541 (8)	0.711 (4)	0.716 (8)	0.245*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.038 (2)	0.052 (2)	0.032 (2)	−0.0045 (18)	0.0159 (17)	−0.0054 (18)
C2	0.042 (2)	0.069 (3)	0.048 (2)	−0.011 (2)	0.0140 (18)	0.000 (2)
C3	0.028 (2)	0.054 (3)	0.056 (2)	−0.0035 (18)	0.0110 (17)	0.001 (2)
C4	0.047 (3)	0.058 (3)	0.073 (3)	−0.003 (2)	0.019 (2)	−0.010 (2)
C5	0.057 (3)	0.047 (3)	0.097 (4)	−0.007 (2)	0.017 (3)	0.012 (3)
C6	0.052 (3)	0.074 (4)	0.074 (3)	−0.004 (2)	0.019 (2)	0.022 (3)
C7	0.032 (2)	0.066 (3)	0.054 (3)	0.001 (2)	0.0117 (18)	0.007 (2)
C8	0.0237 (19)	0.048 (3)	0.057 (2)	0.0011 (17)	0.0101 (17)	0.006 (2)
C9	0.034 (2)	0.057 (3)	0.068 (3)	−0.0009 (19)	0.017 (2)	0.000 (2)
C10	0.042 (3)	0.070 (3)	0.086 (3)	0.011 (2)	0.015 (2)	−0.020 (3)
C11	0.044 (3)	0.109 (4)	0.069 (3)	0.021 (3)	0.014 (2)	−0.021 (3)
C12	0.041 (3)	0.107 (4)	0.055 (3)	0.009 (3)	0.018 (2)	0.009 (3)
C13	0.041 (2)	0.046 (2)	0.042 (2)	−0.0002 (18)	0.0162 (18)	0.0009 (18)
C14	0.049 (2)	0.040 (2)	0.046 (2)	−0.0024 (19)	0.0236 (19)	0.0021 (18)
C15	0.036 (2)	0.038 (2)	0.040 (2)	−0.0002 (17)	0.0171 (17)	0.0012 (17)
C16	0.045 (2)	0.052 (3)	0.058 (3)	0.003 (2)	0.016 (2)	0.002 (2)
C17	0.043 (3)	0.060 (3)	0.088 (3)	0.008 (2)	0.016 (2)	0.004 (3)
C18	0.064 (3)	0.060 (3)	0.094 (4)	0.015 (2)	0.043 (3)	−0.004 (3)
C19	0.064 (3)	0.052 (3)	0.061 (3)	0.000 (2)	0.035 (2)	−0.006 (2)
N1	0.0346 (17)	0.0430 (18)	0.0379 (16)	0.0012 (14)	0.0127 (14)	0.0027 (14)
N2	0.045 (2)	0.0480 (19)	0.0362 (16)	−0.0053 (16)	0.0095 (15)	−0.0029 (15)
Ni1	0.0321 (4)	0.0448 (4)	0.0365 (4)	0.000	0.0142 (3)	0.000
O2	0.0376 (15)	0.0565 (17)	0.0476 (15)	−0.0063 (12)	0.0132 (12)	0.0065 (13)
O4	0.0357 (15)	0.0578 (17)	0.0412 (14)	−0.0039 (12)	0.0143 (12)	−0.0008 (12)
O1W	0.097 (5)	0.066 (4)	0.320 (13)	0.000	0.046 (6)	0.000

Geometric parameters (Å, º) top

C1—O2	1.254 (4)	C13—N1	1.316 (4)
C1—O4	1.260 (4)	C13—N2	1.341 (4)
C1—C2	1.516 (5)	C13—H13	0.9300
C1—Ni1	2.498 (4)	C14—N2	1.374 (4)
C2—C3	1.502 (5)	C14—C15	1.394 (5)
C2—H2A	0.9700	C14—C19	1.395 (5)
C2—H2B	0.9700	C15—C16	1.383 (5)
C3—C4	1.361 (5)	C15—N1	1.405 (4)
C3—C8	1.429 (5)	C16—C17	1.389 (5)
C4—C5	1.403 (6)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.382 (6)
C5—C6	1.356 (6)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.364 (6)
C6—C7	1.401 (6)	C18—H18	0.9300
C6—H6	0.9300	C19—H19	0.9300
C7—C12	1.410 (5)	N1—Ni1	2.021 (3)
C7—C8	1.413 (5)	N2—H2	0.8600
C8—C9	1.410 (5)	Ni1—N1ⁱ	2.021 (3)
C9—C10	1.355 (5)	Ni1—O2	2.055 (2)
C9—H9	0.9300	Ni1—O2ⁱ	2.055 (2)
C10—C11	1.386 (6)	Ni1—O4	2.287 (2)
C10—H10	0.9300	Ni1—O4ⁱ	2.288 (2)
C11—C12	1.364 (6)	Ni1—C1ⁱ	2.498 (4)
C11—H11	0.9300	O1W—H1A	0.90 (8)
C12—H12	0.9300

O2—C1—O4	120.7 (3)	C14—C15—N1	108.8 (3)
O2—C1—C2	118.1 (3)	C15—C16—C17	116.6 (4)
O4—C1—C2	121.2 (3)	C15—C16—H16	121.7
O2—C1—Ni1	55.05 (17)	C17—C16—H16	121.7
O4—C1—Ni1	65.66 (19)	C18—C17—C16	121.6 (4)
C2—C1—Ni1	172.8 (3)	C18—C17—H17	119.2
C3—C2—C1	116.6 (3)	C16—C17—H17	119.2
C3—C2—H2A	108.1	C19—C18—C17	122.7 (4)
C1—C2—H2A	108.1	C19—C18—H18	118.7
C3—C2—H2B	108.1	C17—C18—H18	118.7
C1—C2—H2B	108.1	C18—C19—C14	116.1 (4)
H2A—C2—H2B	107.3	C18—C19—H19	122.0
C4—C3—C8	118.6 (4)	C14—C19—H19	122.0
C4—C3—C2	120.9 (4)	C13—N1—C15	104.6 (3)
C8—C3—C2	120.5 (4)	C13—N1—Ni1	122.2 (2)
C3—C4—C5	121.7 (4)	C15—N1—Ni1	132.9 (2)
C3—C4—H4	119.2	C13—N2—C14	107.3 (3)
C5—C4—H4	119.2	C13—N2—H2	126.4
C6—C5—C4	120.2 (4)	C14—N2—H2	126.4
C6—C5—H5	119.9	N1—Ni1—N1ⁱ	100.03 (15)
C4—C5—H5	119.9	N1—Ni1—O2	101.45 (10)
C5—C6—C7	120.8 (4)	N1ⁱ—Ni1—O2	92.41 (10)
C5—C6—H6	119.6	N1—Ni1—O2ⁱ	92.41 (10)
C7—C6—H6	119.6	N1ⁱ—Ni1—O2ⁱ	101.45 (10)
C6—C7—C12	121.8 (4)	O2—Ni1—O2ⁱ	158.42 (14)
C6—C7—C8	119.1 (4)	N1—Ni1—O4	93.73 (10)
C12—C7—C8	119.1 (4)	N1ⁱ—Ni1—O4	151.40 (10)
C9—C8—C7	117.9 (4)	O2—Ni1—O4	60.13 (9)
C9—C8—C3	122.4 (4)	O2ⁱ—Ni1—O4	102.90 (9)
C7—C8—C3	119.6 (4)	N1—Ni1—O4ⁱ	151.40 (10)
C10—C9—C8	121.7 (4)	N1ⁱ—Ni1—O4ⁱ	93.73 (10)
C10—C9—H9	119.1	O2—Ni1—O4ⁱ	102.90 (9)
C8—C9—H9	119.1	O2ⁱ—Ni1—O4ⁱ	60.13 (9)
C9—C10—C11	120.1 (4)	O4—Ni1—O4ⁱ	85.60 (12)
C9—C10—H10	120.0	N1—Ni1—C1	99.19 (11)
C11—C10—H10	120.0	N1ⁱ—Ni1—C1	121.98 (11)
C12—C11—C10	120.6 (4)	O2—Ni1—C1	30.01 (10)
C12—C11—H11	119.7	O2ⁱ—Ni1—C1	131.69 (12)
C10—C11—H11	119.7	O4—Ni1—C1	30.12 (10)
C11—C12—C7	120.6 (4)	O4ⁱ—Ni1—C1	94.46 (11)
C11—C12—H12	119.7	N1—Ni1—C1ⁱ	121.98 (11)
C7—C12—H12	119.7	N1ⁱ—Ni1—C1ⁱ	99.19 (11)
N1—C13—N2	113.5 (3)	O2—Ni1—C1ⁱ	131.69 (12)
N1—C13—H13	123.3	O2ⁱ—Ni1—C1ⁱ	30.01 (10)
N2—C13—H13	123.3	O4—Ni1—C1ⁱ	94.46 (11)
N2—C14—C15	105.9 (3)	O4ⁱ—Ni1—C1ⁱ	30.12 (10)
N2—C14—C19	132.2 (4)	C1—Ni1—C1ⁱ	115.13 (18)
C15—C14—C19	122.0 (4)	C1—O2—Ni1	94.9 (2)
C16—C15—C14	121.1 (3)	C1—O4—Ni1	84.2 (2)
C16—C15—N1	130.1 (3)

O2—C1—C2—C3	159.6 (3)	C13—N1—Ni1—O2	−156.1 (3)
O4—C1—C2—C3	−21.6 (5)	C15—N1—Ni1—O2	16.7 (3)
Ni1—C1—C2—C3	177 (2)	C13—N1—Ni1—O2ⁱ	7.2 (3)
C1—C2—C3—C4	113.3 (4)	C15—N1—Ni1—O2ⁱ	−180.0 (3)
C1—C2—C3—C8	−66.9 (5)	C13—N1—Ni1—O4	−95.9 (3)
C8—C3—C4—C5	−0.9 (6)	C15—N1—Ni1—O4	76.9 (3)
C2—C3—C4—C5	178.9 (4)	C13—N1—Ni1—O4ⁱ	−8.2 (4)
C3—C4—C5—C6	1.7 (6)	C15—N1—Ni1—O4ⁱ	164.6 (2)
C4—C5—C6—C7	−1.2 (6)	C13—N1—Ni1—C1	−125.7 (3)
C5—C6—C7—C12	179.4 (4)	C15—N1—Ni1—C1	47.1 (3)
C5—C6—C7—C8	0.1 (6)	C13—N1—Ni1—C1ⁱ	1.8 (3)
C6—C7—C8—C9	−179.5 (3)	C15—N1—Ni1—C1ⁱ	174.6 (3)
C12—C7—C8—C9	1.2 (5)	O2—C1—Ni1—N1	−97.0 (2)
C6—C7—C8—C3	0.6 (5)	O4—C1—Ni1—N1	81.5 (2)
C12—C7—C8—C3	−178.7 (3)	C2—C1—Ni1—N1	−116 (2)
C4—C3—C8—C9	179.9 (3)	O2—C1—Ni1—N1ⁱ	11.0 (2)
C2—C3—C8—C9	0.1 (5)	O4—C1—Ni1—N1ⁱ	−170.49 (17)
C4—C3—C8—C7	−0.2 (5)	C2—C1—Ni1—N1ⁱ	−8 (2)
C2—C3—C8—C7	−180.0 (3)	O4—C1—Ni1—O2	178.5 (3)
C7—C8—C9—C10	−1.3 (5)	C2—C1—Ni1—O2	−19 (2)
C3—C8—C9—C10	178.6 (4)	O2—C1—Ni1—O2ⁱ	161.39 (15)
C8—C9—C10—C11	0.2 (6)	O4—C1—Ni1—O2ⁱ	−20.1 (3)
C9—C10—C11—C12	0.9 (6)	C2—C1—Ni1—O2ⁱ	142 (2)
C10—C11—C12—C7	−1.0 (6)	O2—C1—Ni1—O4	−178.5 (3)
C6—C7—C12—C11	−179.4 (4)	C2—C1—Ni1—O4	162 (2)
C8—C7—C12—C11	−0.1 (6)	O2—C1—Ni1—O4ⁱ	108.2 (2)
N2—C14—C15—C16	179.0 (3)	O4—C1—Ni1—O4ⁱ	−73.3 (2)
C19—C14—C15—C16	−0.5 (5)	C2—C1—Ni1—O4ⁱ	89 (2)
N2—C14—C15—N1	−0.7 (4)	O2—C1—Ni1—C1ⁱ	131.1 (2)
C19—C14—C15—N1	179.7 (3)	O4—C1—Ni1—C1ⁱ	−50.43 (17)
C14—C15—C16—C17	0.5 (5)	C2—C1—Ni1—C1ⁱ	112 (2)
N1—C15—C16—C17	−179.8 (3)	O4—C1—O2—Ni1	−1.6 (4)
C15—C16—C17—C18	−0.4 (6)	C2—C1—O2—Ni1	177.3 (3)
C16—C17—C18—C19	0.4 (7)	N1—Ni1—O2—C1	88.6 (2)
C17—C18—C19—C14	−0.4 (6)	N1ⁱ—Ni1—O2—C1	−170.7 (2)
N2—C14—C19—C18	−179.0 (4)	O2ⁱ—Ni1—O2—C1	−40.39 (19)
C15—C14—C19—C18	0.5 (6)	O4—Ni1—O2—C1	0.86 (19)
N2—C13—N1—C15	0.3 (4)	O4ⁱ—Ni1—O2—C1	−76.3 (2)
N2—C13—N1—Ni1	174.9 (2)	C1ⁱ—Ni1—O2—C1	−66.1 (3)
C16—C15—N1—C13	−179.5 (4)	O2—C1—O4—Ni1	1.4 (3)
C14—C15—N1—C13	0.3 (4)	C2—C1—O4—Ni1	−177.4 (3)
C16—C15—N1—Ni1	6.8 (6)	N1—Ni1—O4—C1	−101.9 (2)
C14—C15—N1—Ni1	−173.4 (2)	N1ⁱ—Ni1—O4—C1	17.0 (3)
N1—C13—N2—C14	−0.8 (4)	O2—Ni1—O4—C1	−0.86 (19)
C15—C14—N2—C13	0.9 (4)	O2ⁱ—Ni1—O4—C1	164.7 (2)
C19—C14—N2—C13	−179.5 (4)	O4ⁱ—Ni1—O4—C1	106.7 (2)
C13—N1—Ni1—N1ⁱ	109.3 (3)	C1ⁱ—Ni1—O4—C1	135.57 (19)
C15—N1—Ni1—N1ⁱ	−77.9 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O4	0.90 (8)	2.24 (8)	2.988 (6)	141 (8)
N2—H2···O4ⁱⁱ	0.86	2.00	2.791 (4)	152

Symmetry code: (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₂H₉O₂)₂(C₇H₆N₂)₂]·H₂O
M_r	683.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	11.573 (4), 19.991 (7), 14.290 (5)
β (°)	105.903 (4)
V (Å³)	3179.5 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.952, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	11840, 2807, 1849
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.122, 0.99
No. of reflections	2807
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.43

Computer programs: APEX2 (Bruker 2008), SAINT (Bruker 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), 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—H1A···O4	0.90 (8)	2.24 (8)	2.988 (6)	141 (8)
N2—H2···O4ⁱ	0.86	2.00	2.791 (4)	152

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank Jiangsu Marine Resources Development Research Institute and Huaihai Institute of Technology for support of this work.

References

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