Bis{4-chloro-6-formyl-2-[(E)-2-(1H-imidazol-4-yl-κN3)ethyl­imino­methyl-κN]phenolato-κO1}nickel(II)

Mao, J.-W.; Zhou, H.; Pan, Z.-Q.; Meng, X.-G.

doi:10.1107/S1600536808031577

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Pages m1367-m1368

doi:10.1107/S1600536808031577

Open

access

Bis{4-chloro-6-formyl-2-[(E)-2-(1H-imidazol-4-yl-κN³)ethyliminomethyl-κN]phenolato-κO¹}nickel(II)

Jia-Wei Mao,^a Hong Zhou,^a Zhi-Quan Pan ^a ^* and Xiang-Gao Meng ^b

^aKey Laboratory for Green Chemical Process of Ministry of Education, Wuhan Institute of Technology, Wuhan 430073, People's Republic of China, and ^bDepartment of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: zhiqpan@163.com

(Received 6 September 2008; accepted 30 September 2008; online 4 October 2008)

In the title compound, [Ni(C₁₃H₁₁ClN₃O₂)₂], the Ni^II atom is located on a twofold rotation axis and is six-coordinated by four N atoms and two phenolate O atoms from the two equal Schiff base ligands in a distorted octahedral coordination geometry. The complex molecules are connected by C—H⋯Cl, C—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For related literature on transition metal–Schiff base complexes, see: Casella & Gullotti (1986 ); Hodnett & Dunn (1970 ); Kim et al. (2005 ); May et al. (2004 ). For literature related to the synthesis, see: Taniguchi (1984 ).

Experimental

Crystal data

[Ni(C₁₃H₁₁ClN₃O₂)₂]
M_r = 612.11
Tetragonal, P 4₃ 2₁ 2
a = 13.5883 (16) Å
c = 14.0392 (16) Å
V = 2592.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.00 mm⁻¹
T = 293 (2) K
0.10 × 0.04 × 0.02 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.901, T_max = 0.978
21136 measured reflections
2294 independent reflections
1253 reflections with I > 2σ(I)
R_int = 0.154

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.081
S = 0.82
2294 reflections
177 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 920 Friedel pairs
Flack parameter: 0.02 (3)

Table 1
Selected geometric parameters (Å, °)

Ni1—O1	2.054 (3)
Ni1—N2	2.068 (4)
Ni1—N1	2.102 (4)

O1—Ni1—O1ⁱ	87.37 (17)
O1—Ni1—N2ⁱ	91.40 (14)
O1—Ni1—N2	178.49 (14)
N2ⁱ—Ni1—N2	89.8 (2)
O1—Ni1—N1	88.84 (14)
N2—Ni1—N1	90.27 (15)
O1—Ni1—N1ⁱ	89.72 (13)
N2—Ni1—N1ⁱ	91.14 (15)
N1—Ni1—N1ⁱ	178.0 (2)
Symmetry code: (i) y, x, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯Cl1ⁱⁱ	0.97	2.82	3.475 (5)	125
C12—H12⋯O2ⁱⁱⁱ	0.93	2.36	3.287 (7)	174
N3—H3A⋯O1^iv	0.86	2.06	2.899 (5)	166
Symmetry codes: (ii) $[-x+1, -y, z-{\script{1\over 2}}]$ ; (iii) $[y+{\script{1\over 2}}, -x+{\script{1\over 2}}, z-{\script{3\over 4}}]$ ; (iv) $[-y+{\script{1\over 2}}, x+{\script{1\over 2}}, z-{\script{1\over 4}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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 global, I. DOI: 10.1107/S1600536808031577/hy2154sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031577/hy2154Isup2.hkl

checkCIF report

Comment top

Transition metal–Schiff base complexes have been an interesting field for a long time due to their striking biological activites (Casella & Gullotti, 1986; Hodnett & Dunn, 1970; Kim et al., 2005; May et al., 2004). In this paper, we report the crystal structure of a new nickel(II) complex with a Schiff base ligand, 2-[(E)-(2-(1H-imidazol-4-yl)ethylimino)methyl]-4-chloro -6-formylphenolate.

In the title compound, the Ni^II atom is located on a twofold rotation axis and six-coordinated by four N atoms and two phenolate O atoms from two Schiff base ligands (Fig. 1). The coordination geometry of the Ni atom can be described as distorted octahedral. The two phenolate O atoms and the two imidazole N atoms are located in the equatorial plane, with Ni—O distance of 2.054 (3)Å and Ni—N distance of 2.068 (4)Å (Table 1), and with the mean plane deviation of 0.0147 (2) Å. The other two N atoms from the imino groups of the Schiff base ligands occupy the axial positions, with somewhat long Ni—N distance of 2.102 (4) Å. The complex molecules are connected by C—H···Cl, C—H···O and N—H···O hydrogen bonds (Table 2).

Related literature top

For related literature on transition metal–Schiff base complexes, see: Casella & Gullotti (1986); Hodnett & Dunn (1970); Kim et al. (2005); May et al. (2004). For literature related to the synthesis, see: Taniguchi (1984).

Experimental top

2,6-Diformyl-4-chlorophenol was prepared using the method of Taniguchi (1984). The title compound was synthesized by the following procedure: To an acetonitrile solution (10 ml) of 2,6-diformyl-4-chlorophenol (0.092 g, 0.5 mmol) and Ni(ClO₄)₂.6H₂O (0.018 g, 0.25 mmol), a solution of NaOH (0.041 g, 1 mmol) and histamine dihydrochloride (0.092 g, 0.5 mmol) in 15 ml of absolute methanol was added dropwise. After the mixture was stirred at ambient temperature for about 1 h, a red solution appeared and then the stirring was continued for 3 h. Red needle crystals of the title compound suitable for X-ray diffraction were obtained in about a month.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) x, y, -z.]

Bis{4-chloro-6-formyl-2-[(E)-2-(1H-imidazol-4- yl-κN³)ethyliminomethyl-κN]phenolato-κO¹}nickel(II) top

Crystal data top

[Ni(C₁₃H₁₁ClN₃O₂)₂]	D_x = 1.568 Mg m⁻³
M_r = 612.11	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₃2₁2	Cell parameters from 1360 reflections
Hall symbol: P 4nw 2abw	θ = 2.6–15.1°
a = 13.5883 (16) Å	µ = 1.00 mm⁻¹
c = 14.0392 (16) Å	T = 293 K
V = 2592.2 (5) Å³	Needle, red
Z = 4	0.10 × 0.04 × 0.02 mm
F(000) = 1256

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2294 independent reflections
Radiation source: fine-focus sealed tube	1253 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.154
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.901, T_max = 0.978	k = −16→16
21136 measured reflections	l = −14→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0298P)²] where P = (F_o² + 2F_c²)/3
S = 0.82	(Δ/σ)_max = 0.003
2294 reflections	Δρ_max = 0.35 e Å⁻³
177 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 920 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (3)

Crystal data top

[Ni(C₁₃H₁₁ClN₃O₂)₂]	Z = 4
M_r = 612.11	Mo Kα radiation
Tetragonal, P4₃2₁2	µ = 1.00 mm⁻¹
a = 13.5883 (16) Å	T = 293 K
c = 14.0392 (16) Å	0.10 × 0.04 × 0.02 mm
V = 2592.2 (5) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2294 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1253 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.978	R_int = 0.154
21136 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.081	Δρ_max = 0.35 e Å⁻³
S = 0.82	Δρ_min = −0.24 e Å⁻³
2294 reflections	Absolute structure: Flack (1983), 920 Friedel pairs
177 parameters	Absolute structure parameter: 0.02 (3)
0 restraints

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. The reason of the large R_intvalue is the poor quality and small size of the crystal sample. Although many efforts were made to select better crystal for experiment, each time we failed.

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

	x	y	z	U_iso*/U_eq
Ni1	0.23545 (4)	0.23545 (4)	0.0000	0.0433 (3)
C1	0.2375 (4)	0.0575 (3)	0.1277 (3)	0.0428 (12)
C2	0.2104 (4)	0.0113 (4)	0.2139 (4)	0.0564 (15)
C3	0.2586 (4)	−0.0728 (4)	0.2478 (4)	0.0656 (14)
H3	0.2381	−0.1026	0.3041	0.079*
C4	0.3356 (4)	−0.1106 (4)	0.1977 (5)	0.0642 (17)
C5	0.3666 (4)	−0.0659 (4)	0.1150 (4)	0.0593 (15)
H5	0.4202	−0.0920	0.0825	0.071*
C6	0.3205 (4)	0.0165 (3)	0.0790 (4)	0.0455 (13)
C7	0.1300 (4)	0.0521 (5)	0.2722 (4)	0.0800 (19)
H7	0.1037	0.1125	0.2545	0.096*
C8	0.3581 (3)	0.0522 (4)	−0.0096 (4)	0.0519 (13)
H8	0.4055	0.0129	−0.0384	0.062*
C9	0.3904 (4)	0.1472 (4)	−0.1444 (4)	0.0700 (17)
H9A	0.4022	0.0839	−0.1743	0.084*
H9B	0.4539	0.1760	−0.1294	0.084*
C10	0.3368 (4)	0.2136 (4)	−0.2143 (3)	0.0636 (15)
H10A	0.3701	0.2112	−0.2754	0.076*
H10B	0.2704	0.1892	−0.2233	0.076*
C11	0.3326 (4)	0.3166 (4)	−0.1810 (4)	0.0500 (14)
C12	0.3728 (4)	0.4001 (4)	−0.2169 (4)	0.0620 (16)
H12	0.4097	0.4056	−0.2724	0.074*
C13	0.2960 (3)	0.4340 (4)	−0.0856 (4)	0.0504 (14)
H13	0.2707	0.4695	−0.0345	0.060*
Cl1	0.39581 (12)	−0.21688 (11)	0.23773 (13)	0.1081 (7)
N1	0.3352 (3)	0.1319 (3)	−0.0552 (3)	0.0487 (11)
N2	0.2844 (3)	0.3389 (3)	−0.0971 (3)	0.0480 (11)
N3	0.3486 (3)	0.4739 (3)	−0.1563 (3)	0.0584 (12)
H3A	0.3641	0.5349	−0.1622	0.070*
O1	0.1862 (2)	0.1302 (2)	0.0935 (2)	0.0494 (9)
O2	0.0962 (3)	0.0119 (3)	0.3416 (3)	0.1061 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0453 (3)	0.0453 (3)	0.0393 (5)	0.0010 (4)	0.0040 (3)	−0.0040 (3)
C1	0.038 (3)	0.050 (3)	0.040 (3)	−0.012 (3)	−0.004 (3)	0.003 (3)
C2	0.057 (4)	0.056 (4)	0.056 (4)	−0.014 (3)	−0.008 (3)	0.009 (3)
C3	0.067 (4)	0.064 (4)	0.066 (4)	−0.024 (3)	−0.020 (5)	0.016 (4)
C4	0.059 (4)	0.055 (4)	0.079 (5)	0.001 (3)	−0.026 (4)	0.017 (4)
C5	0.041 (3)	0.060 (4)	0.077 (5)	−0.003 (3)	−0.011 (3)	−0.002 (3)
C6	0.043 (3)	0.043 (3)	0.050 (4)	−0.003 (3)	−0.006 (3)	0.001 (3)
C7	0.080 (5)	0.115 (5)	0.045 (5)	−0.021 (4)	0.001 (4)	0.030 (4)
C8	0.048 (3)	0.044 (3)	0.064 (4)	0.007 (3)	0.004 (3)	−0.013 (3)
C9	0.094 (4)	0.056 (4)	0.060 (4)	0.015 (3)	0.028 (4)	0.004 (3)
C10	0.082 (4)	0.069 (4)	0.040 (4)	0.011 (3)	0.020 (3)	−0.006 (3)
C11	0.060 (4)	0.053 (4)	0.038 (4)	0.003 (3)	0.002 (3)	0.002 (3)
C12	0.070 (4)	0.068 (4)	0.048 (4)	0.015 (3)	0.018 (3)	0.000 (3)
C13	0.052 (4)	0.054 (4)	0.045 (4)	0.004 (3)	0.009 (3)	0.006 (3)
Cl1	0.1068 (12)	0.0770 (11)	0.1405 (16)	0.0095 (10)	−0.0362 (12)	0.0368 (12)
N1	0.052 (3)	0.054 (3)	0.041 (3)	−0.001 (2)	0.009 (2)	−0.003 (2)
N2	0.063 (3)	0.042 (3)	0.039 (3)	−0.003 (2)	0.003 (2)	0.000 (2)
N3	0.063 (3)	0.053 (3)	0.059 (3)	−0.009 (2)	0.006 (3)	0.018 (3)
O1	0.043 (2)	0.059 (2)	0.046 (2)	0.0090 (17)	0.0044 (17)	0.0083 (18)
O2	0.116 (4)	0.135 (4)	0.068 (4)	−0.013 (3)	0.017 (3)	0.026 (3)

Geometric parameters (Å, º) top

Ni1—O1	2.054 (3)	C7—H7	0.9300
Ni1—O1ⁱ	2.054 (3)	C8—N1	1.296 (5)
Ni1—N2ⁱ	2.068 (4)	C8—H8	0.9300
Ni1—N2	2.068 (4)	C9—N1	1.474 (5)
Ni1—N1	2.102 (4)	C9—C10	1.519 (6)
Ni1—N1ⁱ	2.102 (4)	C9—H9A	0.9700
C1—O1	1.301 (5)	C9—H9B	0.9700
C1—C2	1.412 (6)	C10—C11	1.477 (6)
C1—C6	1.431 (6)	C10—H10A	0.9700
C2—C3	1.401 (6)	C10—H10B	0.9700
C2—C7	1.474 (7)	C11—C12	1.355 (6)
C3—C4	1.362 (7)	C11—N2	1.382 (5)
C3—H3	0.9300	C12—N3	1.356 (5)
C4—C5	1.376 (7)	C12—H12	0.9300
C4—Cl1	1.752 (5)	C13—N2	1.312 (5)
C5—C6	1.380 (6)	C13—N3	1.337 (5)
C5—H5	0.9300	C13—H13	0.9300
C6—C8	1.429 (6)	N3—H3A	0.8600
C7—O2	1.208 (5)

O1—Ni1—O1ⁱ	87.37 (17)	C2—C7—H7	117.9
O1—Ni1—N2ⁱ	91.40 (14)	N1—C8—C6	128.9 (5)
O1ⁱ—Ni1—N2ⁱ	178.49 (14)	N1—C8—H8	115.5
O1—Ni1—N2	178.49 (14)	C6—C8—H8	115.5
O1ⁱ—Ni1—N2	91.40 (14)	N1—C9—C10	112.8 (4)
N2ⁱ—Ni1—N2	89.8 (2)	N1—C9—H9A	109.0
O1—Ni1—N1	88.84 (14)	C10—C9—H9A	109.0
O1ⁱ—Ni1—N1	89.72 (13)	N1—C9—H9B	109.0
N2ⁱ—Ni1—N1	91.14 (15)	C10—C9—H9B	109.0
N2—Ni1—N1	90.27 (15)	H9A—C9—H9B	107.8
O1—Ni1—N1ⁱ	89.72 (13)	C11—C10—C9	112.2 (4)
O1ⁱ—Ni1—N1ⁱ	88.84 (14)	C11—C10—H10A	109.2
N2ⁱ—Ni1—N1ⁱ	90.27 (15)	C9—C10—H10A	109.2
N2—Ni1—N1ⁱ	91.14 (15)	C11—C10—H10B	109.2
N1—Ni1—N1ⁱ	178.0 (2)	C9—C10—H10B	109.2
O1—C1—C2	120.9 (5)	H10A—C10—H10B	107.9
O1—C1—C6	122.8 (4)	C12—C11—N2	108.9 (5)
C2—C1—C6	116.2 (5)	C12—C11—C10	131.3 (5)
C3—C2—C1	122.2 (5)	N2—C11—C10	119.7 (5)
C3—C2—C7	117.6 (5)	C11—C12—N3	106.8 (5)
C1—C2—C7	120.2 (5)	C11—C12—H12	126.6
C4—C3—C2	119.4 (5)	N3—C12—H12	126.6
C4—C3—H3	120.3	N2—C13—N3	111.9 (5)
C2—C3—H3	120.3	N2—C13—H13	124.1
C3—C4—C5	120.3 (5)	N3—C13—H13	124.1
C3—C4—Cl1	120.3 (5)	C8—N1—C9	114.6 (4)
C5—C4—Cl1	119.4 (5)	C8—N1—Ni1	122.1 (3)
C4—C5—C6	121.9 (5)	C9—N1—Ni1	123.2 (3)
C4—C5—H5	119.0	C13—N2—C11	105.3 (4)
C6—C5—H5	119.0	C13—N2—Ni1	128.9 (4)
C5—C6—C8	115.6 (5)	C11—N2—Ni1	124.4 (3)
C5—C6—C1	119.9 (5)	C13—N3—C12	107.2 (4)
C8—C6—C1	124.4 (4)	C13—N3—H3A	126.4
O2—C7—C2	124.1 (6)	C12—N3—H3A	126.4
O2—C7—H7	117.9	C1—O1—Ni1	126.1 (3)

O1—C1—C2—C3	173.9 (4)	C10—C9—N1—Ni1	−28.0 (6)
C6—C1—C2—C3	−3.1 (6)	O1—Ni1—N1—C8	−17.2 (4)
O1—C1—C2—C7	−7.0 (7)	O1ⁱ—Ni1—N1—C8	−104.6 (4)
C6—C1—C2—C7	176.0 (4)	N2ⁱ—Ni1—N1—C8	74.1 (4)
C1—C2—C3—C4	1.5 (7)	N2—Ni1—N1—C8	164.0 (4)
C7—C2—C3—C4	−177.6 (5)	O1—Ni1—N1—C9	167.8 (4)
C2—C3—C4—C5	0.8 (8)	O1ⁱ—Ni1—N1—C9	80.4 (4)
C2—C3—C4—Cl1	−179.0 (3)	N2ⁱ—Ni1—N1—C9	−100.8 (4)
C3—C4—C5—C6	−1.3 (8)	N2—Ni1—N1—C9	−11.0 (4)
Cl1—C4—C5—C6	178.5 (4)	N3—C13—N2—C11	−0.2 (5)
C4—C5—C6—C8	−177.3 (5)	N3—C13—N2—Ni1	166.5 (3)
C4—C5—C6—C1	−0.4 (7)	C12—C11—N2—C13	0.6 (6)
O1—C1—C6—C5	−174.4 (4)	C10—C11—N2—C13	178.1 (5)
C2—C1—C6—C5	2.5 (6)	C12—C11—N2—Ni1	−166.8 (3)
O1—C1—C6—C8	2.2 (7)	C10—C11—N2—Ni1	10.7 (6)
C2—C1—C6—C8	179.2 (4)	N2ⁱ—Ni1—N2—C13	−52.1 (4)
C3—C2—C7—O2	−8.3 (8)	N1—Ni1—N2—C13	−143.3 (4)
C1—C2—C7—O2	172.5 (5)	N2ⁱ—Ni1—N2—C11	112.2 (4)
C5—C6—C8—N1	−173.5 (5)	N1—Ni1—N2—C11	21.0 (4)
C1—C6—C8—N1	9.8 (8)	N1ⁱ—Ni1—N2—C11	−157.6 (4)
N1—C9—C10—C11	69.3 (6)	N2—C13—N3—C12	−0.3 (6)
C9—C10—C11—C12	115.1 (6)	C11—C12—N3—C13	0.6 (6)
C9—C10—C11—N2	−61.8 (6)	C2—C1—O1—Ni1	157.3 (3)
N2—C11—C12—N3	−0.7 (6)	C6—C1—O1—Ni1	−25.9 (6)
C10—C11—C12—N3	−177.9 (5)	O1ⁱ—Ni1—O1—C1	118.8 (4)
C6—C8—N1—C9	178.7 (5)	N1—Ni1—O1—C1	29.0 (4)
C6—C8—N1—Ni1	3.3 (7)	N1ⁱ—Ni1—O1—C1	−152.4 (3)
C10—C9—N1—C8	156.6 (4)

Symmetry code: (i) y, x, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···Cl1ⁱⁱ	0.97	2.82	3.475 (5)	125
C12—H12···O2ⁱⁱⁱ	0.93	2.36	3.287 (7)	174
N3—H3A···O1^iv	0.86	2.06	2.899 (5)	166

Symmetry codes: (ii) −x+1, −y, z−1/2; (iii) y+1/2, −x+1/2, z−3/4; (iv) −y+1/2, x+1/2, z−1/4.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₃H₁₁ClN₃O₂)₂]
M_r	612.11
Crystal system, space group	Tetragonal, P4₃2₁2
Temperature (K)	293
a, c (Å)	13.5883 (16), 14.0392 (16)
V (Å³)	2592.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.00
Crystal size (mm)	0.10 × 0.04 × 0.02

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.901, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	21136, 2294, 1253
R_int	0.154
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.081, 0.82
No. of reflections	2294
No. of parameters	177
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.24
Absolute structure	Flack (1983), 920 Friedel pairs
Absolute structure parameter	0.02 (3)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ni1—O1	2.054 (3)	Ni1—N1	2.102 (4)
Ni1—N2	2.068 (4)

O1—Ni1—O1ⁱ	87.37 (17)	N2—Ni1—N1	90.27 (15)
O1—Ni1—N2ⁱ	91.40 (14)	O1—Ni1—N1ⁱ	89.72 (13)
O1—Ni1—N2	178.49 (14)	N2—Ni1—N1ⁱ	91.14 (15)
N2ⁱ—Ni1—N2	89.8 (2)	N1—Ni1—N1ⁱ	178.0 (2)
O1—Ni1—N1	88.84 (14)

Symmetry code: (i) y, x, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···Cl1ⁱⁱ	0.97	2.82	3.475 (5)	125
C12—H12···O2ⁱⁱⁱ	0.93	2.36	3.287 (7)	174
N3—H3A···O1^iv	0.86	2.06	2.899 (5)	166

Symmetry codes: (ii) −x+1, −y, z−1/2; (iii) y+1/2, −x+1/2, z−3/4; (iv) −y+1/2, x+1/2, z−1/4.

Acknowledgements

The authors gratefully acknowledge financial support from the Midlife and Youth Excellent Innovation Group of Hubei Province, China (grant No. T200802), the Key Foundation of the Education Department of Hubei Province, China (grant No. D20081503), and the Graduate Innovation Foundation of Wuhan Institute of Technology (RGCT200804).

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Casella, L. & Gullotti, M. (1986). Inorg. Chem. 25, 1293–1303. CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hodnett, E. M. & Dunn, W. J. (1970). J. Med. Chem. 13, 768–770. CrossRef CAS PubMed Web of Science Google Scholar
Kim, H.-J., Kim, W., Lough, A. J., Kim, B. M. & Chin, J. (2005). J. Am. Chem. Soc. 127, 16776–16777. Web of Science CSD CrossRef PubMed CAS Google Scholar
May, J. P., Ting, R., Lermer, L., Thomas, J. M., Roupioz, Y. & Perrin, D. M. (2004). J. Am. Chem. Soc. 126, 4145–4156. Web of Science CrossRef PubMed CAS 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
Taniguchi, S. (1984). Bull. Chem. Soc. Jpn, 57, 2683–2689. CrossRef CAS Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.