Bis[(E)-4-chloro-2-(cyclo­hexyl­imino­meth­yl)phenolato]nickel(II)

Xia, D.-S.; Chen, W.; Zhao, Y.-M.; Zeng, Q.-F.

doi:10.1107/S1600536808015390

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page m843

doi:10.1107/S1600536808015390

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Bis[(E)-4-chloro-2-(cyclohexyliminomethyl)phenolato]nickel(II)

Dong-Sheng Xia,^a Wu Chen,^a Yu-Min Zhao ^a and Qing-Fu Zeng ^a ^*

^aEngineering Research Center for the Clean Production of Textile Printing, Ministry of Education, Wuhan University of Science and Engineering, Wuhan 430073, People's Republic of China
^*Correspondence e-mail: qingfu_zeng@163.com

(Received 21 May 2008; accepted 22 May 2008; online 30 May 2008)

In the title mononuclear nickel(II) complex, [Ni(C₁₃H₁₅ClNO)₂], the Ni^II atom is four-coordinated in a tetrahedral geometry by the N and O atoms of the two Schiff base ligands.

Related literature

For related structures, see: Cheng et al. (2007 ); Li et al. (2007 ); Qiu et al. (2006 ); Shi et al. (2007 ); Wang et al. (2005 ); Zhu et al. (2003 ).

Experimental

Crystal data

[Ni(C₁₃H₁₅ClNO)₂]
M_r = 532.13
Orthorhombic, P b c a
a = 14.871 (3) Å
b = 13.563 (3) Å
c = 24.993 (5) Å
V = 5040.9 (17) Å³
Z = 8
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 298 (2) K
0.42 × 0.38 × 0.37 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.663, T_max = 0.686
4933 measured reflections
R_int = 0.023
4693 independent reflections
2416 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.162
S = 1.04
4693 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ni1—O1	1.911 (4)
Ni1—O2	1.911 (4)
Ni1—N1	2.016 (5)
Ni1—N2	2.018 (5)

O1—Ni1—O2	120.45 (18)
O1—Ni1—N1	95.93 (18)
O2—Ni1—N1	112.44 (18)
O1—Ni1—N2	113.09 (19)
O2—Ni1—N2	94.54 (17)
N1—Ni1—N2	122.42 (18)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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/S1600536808015390/sj2506sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015390/sj2506Isup2.hkl

checkCIF report

Comment top

As part of our ongoing interest in the structure of nickel(II) complexes (Zhu et al., 2003), we report herein the crystal structure of the title compound, a new mononuclear nickel(II) complex, (I), Fig. 1, derived from the Schiff base ligand 4-chloro-2-(cyclohexyliminomethyl)phenol.

The Ni^II atom in (I) is four-coordinate in a tetrahedral geometry, binding to the N and two O atoms of the two Schiff base ligands. The coordinate bond values (Table 1) are comparable to values observed in other similar nickel(II) complexes (Shi et al., 2007; Li et al., 2007; Cheng et al., 2007; Qiu et al., 2006; Wang et al., 2005).

Related literature top

For related structures, see: Cheng et al. (2007); Li et al. (2007); Qiu et al. (2006); Shi et al. (2007); Wang et al. (2005); Zhu et al. (2003).

Experimental top

5-Chlorosalicylaldehyde (15.6 mg, 0.1 mmol), cyclohexylamine (9.9 mg, 0.1 mmol), and NiCl₂.6H₂O (23.8 mg, 0.1 mmol) were dissolved in methanol (30 ml). The mixture was stirred for 30 min at room temperature. The resulting solution was left in air for a few days, yielding green crystals.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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. The structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Bis[(E)-4-chloro-2-(cyclohexyliminomethyl)phenolato]nickel(II) top

Crystal data top

[Ni(C₁₃H₁₅ClNO)₂]	F(000) = 2224
M_r = 532.13	D_x = 1.402 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2013 reflections
a = 14.871 (3) Å	θ = 2.3–25.3°
b = 13.563 (3) Å	µ = 1.01 mm⁻¹
c = 24.993 (5) Å	T = 298 K
V = 5040.9 (17) Å³	Block, green
Z = 8	0.42 × 0.38 × 0.37 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4693 independent reflections
Radiation source: fine-focus sealed tube	2416 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 25.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→18
T_min = 0.663, T_max = 0.686	k = −15→16
4933 measured reflections	l = −30→30

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0617P)²] where P = (F_o² + 2F_c²)/3
4693 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Ni(C₁₃H₁₅ClNO)₂]	V = 5040.9 (17) Å³
M_r = 532.13	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.871 (3) Å	µ = 1.01 mm⁻¹
b = 13.563 (3) Å	T = 298 K
c = 24.993 (5) Å	0.42 × 0.38 × 0.37 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4693 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2416 reflections with I > 2σ(I)
T_min = 0.663, T_max = 0.686	R_int = 0.023
4933 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.04	Δρ_max = 0.32 e Å⁻³
4693 reflections	Δρ_min = −0.45 e Å⁻³
298 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
Ni1	0.14197 (4)	0.91723 (5)	0.19419 (3)	0.0418 (2)
Cl1	−0.11240 (16)	0.61620 (16)	0.01142 (8)	0.1021 (8)
Cl2	0.32265 (12)	1.23468 (13)	0.39664 (7)	0.0768 (6)
O1	0.1603 (3)	0.8322 (3)	0.13420 (17)	0.0644 (12)
O2	0.2180 (3)	0.9080 (3)	0.25567 (16)	0.0586 (11)
N1	0.0151 (3)	0.8732 (3)	0.20947 (18)	0.0460 (12)
N2	0.1735 (3)	1.0591 (3)	0.17874 (19)	0.0482 (13)
C1	0.0059 (4)	0.7796 (4)	0.1256 (2)	0.0473 (15)
C2	0.0954 (4)	0.7884 (4)	0.1071 (3)	0.0524 (16)
C3	0.1154 (4)	0.7475 (5)	0.0575 (3)	0.0618 (17)
H3	0.1729	0.7560	0.0435	0.074*
C4	0.0536 (5)	0.6954 (5)	0.0286 (3)	0.069 (2)
H4	0.0699	0.6676	−0.0040	0.083*
C5	−0.0337 (5)	0.6836 (5)	0.0478 (3)	0.0648 (19)
C6	−0.0575 (4)	0.7255 (4)	0.0950 (2)	0.0586 (17)
H6	−0.1162	0.7187	0.1075	0.070*
C7	−0.0277 (4)	0.8180 (4)	0.1755 (2)	0.0501 (16)
H7	−0.0865	0.8014	0.1844	0.060*
C8	−0.0329 (4)	0.9005 (4)	0.2591 (2)	0.0486 (15)
H8	−0.0970	0.8860	0.2545	0.058*
C9	0.0027 (5)	0.8394 (5)	0.3045 (2)	0.0683 (19)
H9A	0.0673	0.8485	0.3072	0.082*
H9B	−0.0086	0.7703	0.2973	0.082*
C10	−0.0411 (5)	0.8677 (5)	0.3573 (3)	0.083 (2)
H10A	−0.1047	0.8520	0.3560	0.100*
H10B	−0.0142	0.8298	0.3861	0.100*
C11	−0.0291 (5)	0.9768 (6)	0.3682 (3)	0.079 (2)
H11A	−0.0592	0.9944	0.4013	0.095*
H11B	0.0344	0.9920	0.3721	0.095*
C12	−0.0682 (5)	1.0352 (5)	0.3224 (3)	0.072 (2)
H12A	−0.1320	1.0212	0.3195	0.087*
H12B	−0.0612	1.1051	0.3295	0.087*
C13	−0.0222 (4)	1.0095 (4)	0.2705 (3)	0.0577 (17)
H13A	0.0412	1.0259	0.2728	0.069*
H13B	−0.0483	1.0476	0.2416	0.069*
C14	0.2385 (3)	1.0838 (4)	0.2672 (2)	0.0449 (14)
C15	0.2402 (4)	0.9843 (5)	0.2852 (3)	0.0498 (16)
C16	0.2693 (4)	0.9689 (5)	0.3380 (3)	0.0601 (18)
H16	0.2719	0.9045	0.3507	0.072*
C17	0.2941 (4)	1.0439 (5)	0.3720 (3)	0.0622 (18)
H17	0.3118	1.0304	0.4069	0.075*
C18	0.2920 (4)	1.1408 (5)	0.3530 (2)	0.0530 (16)
C19	0.2665 (4)	1.1603 (4)	0.3020 (2)	0.0520 (16)
H19	0.2674	1.2250	0.2897	0.062*
C20	0.2118 (4)	1.1130 (4)	0.2144 (2)	0.0507 (15)
H20	0.2236	1.1781	0.2049	0.061*
C21	0.1556 (4)	1.1016 (4)	0.1257 (2)	0.0551 (17)
H21	0.1659	1.1729	0.1275	0.066*
C22	0.2191 (4)	1.0582 (5)	0.0844 (2)	0.0644 (19)
H22A	0.2157	0.9868	0.0860	0.077*
H22B	0.2802	1.0774	0.0931	0.077*
C23	0.1970 (4)	1.0921 (6)	0.0278 (2)	0.076 (2)
H23A	0.2083	1.1623	0.0247	0.092*
H23B	0.2360	1.0584	0.0026	0.092*
C24	0.0995 (4)	1.0709 (5)	0.0138 (3)	0.071 (2)
H24A	0.0894	1.0002	0.0135	0.085*
H24B	0.0863	1.0961	−0.0217	0.085*
C25	0.0371 (4)	1.1194 (5)	0.0545 (3)	0.0648 (19)
H25A	0.0444	1.1904	0.0530	0.078*
H25B	−0.0249	1.1041	0.0457	0.078*
C26	0.0575 (4)	1.0836 (5)	0.1107 (2)	0.0575 (16)
H26A	0.0446	1.0136	0.1131	0.069*
H26B	0.0189	1.1177	0.1359	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0369 (4)	0.0331 (4)	0.0554 (5)	−0.0024 (3)	0.0001 (4)	0.0037 (4)
Cl1	0.1222 (19)	0.1082 (17)	0.0760 (14)	−0.0257 (14)	−0.0106 (13)	−0.0268 (12)
Cl2	0.0907 (13)	0.0690 (12)	0.0706 (12)	−0.0022 (10)	−0.0220 (10)	−0.0051 (10)
O1	0.054 (3)	0.055 (3)	0.085 (3)	−0.005 (2)	0.012 (2)	−0.010 (2)
O2	0.064 (3)	0.038 (2)	0.074 (3)	−0.003 (2)	−0.008 (2)	0.006 (2)
N1	0.047 (3)	0.039 (3)	0.052 (3)	−0.002 (2)	0.007 (3)	−0.002 (2)
N2	0.045 (3)	0.045 (3)	0.055 (3)	−0.003 (2)	−0.012 (2)	0.006 (2)
C1	0.057 (4)	0.039 (3)	0.047 (4)	0.002 (3)	0.007 (3)	−0.001 (3)
C2	0.055 (4)	0.037 (3)	0.065 (5)	0.003 (3)	0.012 (4)	0.007 (3)
C3	0.064 (4)	0.056 (4)	0.066 (5)	0.008 (4)	0.013 (4)	−0.001 (4)
C4	0.097 (6)	0.055 (4)	0.055 (4)	0.016 (4)	0.011 (4)	−0.003 (4)
C5	0.090 (5)	0.051 (4)	0.054 (4)	0.000 (4)	0.000 (4)	−0.006 (3)
C6	0.064 (4)	0.059 (4)	0.053 (4)	0.000 (4)	−0.003 (4)	0.004 (3)
C7	0.045 (4)	0.046 (4)	0.059 (4)	−0.005 (3)	0.004 (3)	0.000 (3)
C8	0.044 (3)	0.045 (4)	0.057 (4)	−0.005 (3)	0.002 (3)	−0.003 (3)
C9	0.097 (5)	0.052 (4)	0.057 (4)	0.004 (4)	0.017 (4)	0.001 (4)
C10	0.107 (6)	0.074 (5)	0.070 (5)	0.006 (5)	0.011 (5)	−0.001 (4)
C11	0.085 (6)	0.087 (6)	0.064 (5)	0.000 (5)	0.005 (4)	−0.021 (5)
C12	0.081 (5)	0.059 (4)	0.077 (5)	0.002 (4)	0.005 (4)	−0.020 (4)
C13	0.057 (4)	0.043 (4)	0.073 (5)	0.004 (3)	0.009 (3)	−0.010 (3)
C14	0.038 (3)	0.043 (3)	0.054 (4)	−0.003 (3)	−0.005 (3)	0.010 (3)
C15	0.039 (3)	0.048 (4)	0.062 (4)	0.003 (3)	−0.001 (3)	0.008 (3)
C16	0.054 (4)	0.052 (4)	0.074 (5)	0.006 (3)	−0.007 (4)	0.026 (4)
C17	0.057 (4)	0.072 (5)	0.057 (4)	−0.001 (4)	−0.006 (3)	0.007 (4)
C18	0.049 (4)	0.056 (4)	0.054 (4)	0.000 (3)	−0.009 (3)	0.004 (3)
C19	0.046 (4)	0.048 (4)	0.062 (4)	0.001 (3)	−0.003 (3)	0.007 (4)
C20	0.045 (3)	0.044 (4)	0.063 (4)	0.000 (3)	−0.005 (3)	0.011 (3)
C21	0.059 (4)	0.039 (4)	0.067 (4)	−0.004 (3)	−0.019 (3)	0.006 (3)
C22	0.045 (4)	0.084 (5)	0.064 (4)	−0.004 (3)	−0.005 (3)	0.017 (4)
C23	0.063 (5)	0.099 (6)	0.067 (5)	−0.013 (4)	−0.007 (4)	0.010 (4)
C24	0.069 (5)	0.081 (5)	0.064 (5)	−0.004 (4)	−0.015 (4)	0.003 (4)
C25	0.063 (4)	0.060 (4)	0.072 (5)	0.001 (4)	−0.021 (4)	0.002 (4)
C26	0.053 (4)	0.053 (4)	0.066 (4)	0.004 (3)	−0.009 (3)	0.000 (4)

Geometric parameters (Å, º) top

Ni1—O1	1.911 (4)	C11—H11B	0.9700
Ni1—O2	1.911 (4)	C12—C13	1.508 (8)
Ni1—N1	2.016 (5)	C12—H12A	0.9700
Ni1—N2	2.018 (5)	C12—H12B	0.9700
Cl1—C5	1.740 (7)	C13—H13A	0.9700
Cl2—C18	1.737 (6)	C13—H13B	0.9700
O1—C2	1.321 (7)	C14—C19	1.417 (7)
O2—C15	1.314 (7)	C14—C15	1.423 (7)
N1—C7	1.298 (7)	C14—C20	1.434 (7)
N1—C8	1.478 (7)	C15—C16	1.404 (8)
N2—C20	1.286 (7)	C16—C17	1.374 (8)
N2—C21	1.470 (7)	C16—H16	0.9300
C1—C2	1.415 (8)	C17—C18	1.398 (8)
C1—C6	1.419 (8)	C17—H17	0.9300
C1—C7	1.440 (7)	C18—C19	1.356 (7)
C2—C3	1.390 (8)	C19—H19	0.9300
C3—C4	1.366 (8)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.516 (8)
C4—C5	1.394 (9)	C21—C26	1.526 (7)
C4—H4	0.9300	C21—H21	0.9800
C5—C6	1.358 (8)	C22—C23	1.525 (8)
C6—H6	0.9300	C22—H22A	0.9700
C7—H7	0.9300	C22—H22B	0.9700
C8—C9	1.502 (8)	C23—C24	1.520 (8)
C8—C13	1.514 (7)	C23—H23A	0.9700
C8—H8	0.9800	C23—H23B	0.9700
C9—C10	1.520 (8)	C24—C25	1.527 (8)
C9—H9A	0.9700	C24—H24A	0.9700
C9—H9B	0.9700	C24—H24B	0.9700
C10—C11	1.516 (9)	C25—C26	1.516 (8)
C10—H10A	0.9700	C25—H25A	0.9700
C10—H10B	0.9700	C25—H25B	0.9700
C11—C12	1.508 (9)	C26—H26A	0.9700
C11—H11A	0.9700	C26—H26B	0.9700

O1—Ni1—O2	120.45 (18)	H12A—C12—H12B	108.0
O1—Ni1—N1	95.93 (18)	C12—C13—C8	109.9 (5)
O2—Ni1—N1	112.44 (18)	C12—C13—H13A	109.7
O1—Ni1—N2	113.09 (19)	C8—C13—H13A	109.7
O2—Ni1—N2	94.54 (17)	C12—C13—H13B	109.7
N1—Ni1—N2	122.42 (18)	C8—C13—H13B	109.7
C2—O1—Ni1	124.8 (4)	H13A—C13—H13B	108.2
C15—O2—Ni1	123.3 (4)	C19—C14—C15	119.7 (5)
C7—N1—C8	117.2 (5)	C19—C14—C20	116.4 (5)
C7—N1—Ni1	120.4 (4)	C15—C14—C20	124.0 (5)
C8—N1—Ni1	122.4 (4)	O2—C15—C16	119.3 (6)
C20—N2—C21	118.8 (5)	O2—C15—C14	124.4 (6)
C20—N2—Ni1	120.8 (4)	C16—C15—C14	116.3 (6)
C21—N2—Ni1	120.3 (4)	C17—C16—C15	123.6 (6)
C2—C1—C6	119.5 (6)	C17—C16—H16	118.2
C2—C1—C7	125.5 (6)	C15—C16—H16	118.2
C6—C1—C7	115.0 (5)	C16—C17—C18	118.7 (6)
O1—C2—C3	118.7 (6)	C16—C17—H17	120.6
O1—C2—C1	123.8 (6)	C18—C17—H17	120.6
C3—C2—C1	117.4 (6)	C19—C18—C17	120.6 (6)
C4—C3—C2	122.2 (6)	C19—C18—Cl2	121.4 (5)
C4—C3—H3	118.9	C17—C18—Cl2	118.1 (5)
C2—C3—H3	118.9	C18—C19—C14	121.1 (6)
C3—C4—C5	120.3 (6)	C18—C19—H19	119.5
C3—C4—H4	119.8	C14—C19—H19	119.5
C5—C4—H4	119.8	N2—C20—C14	127.1 (5)
C6—C5—C4	119.6 (7)	N2—C20—H20	116.5
C6—C5—Cl1	119.9 (6)	C14—C20—H20	116.5
C4—C5—Cl1	120.5 (6)	N2—C21—C22	110.4 (5)
C5—C6—C1	120.8 (6)	N2—C21—C26	109.4 (5)
C5—C6—H6	119.6	C22—C21—C26	111.4 (5)
C1—C6—H6	119.6	N2—C21—H21	108.5
N1—C7—C1	127.2 (6)	C22—C21—H21	108.5
N1—C7—H7	116.4	C26—C21—H21	108.5
C1—C7—H7	116.4	C21—C22—C23	112.4 (5)
N1—C8—C9	109.0 (5)	C21—C22—H22A	109.1
N1—C8—C13	110.7 (5)	C23—C22—H22A	109.1
C9—C8—C13	111.0 (5)	C21—C22—H22B	109.1
N1—C8—H8	108.7	C23—C22—H22B	109.1
C9—C8—H8	108.7	H22A—C22—H22B	107.9
C13—C8—H8	108.7	C24—C23—C22	111.2 (5)
C8—C9—C10	111.5 (5)	C24—C23—H23A	109.4
C8—C9—H9A	109.3	C22—C23—H23A	109.4
C10—C9—H9A	109.3	C24—C23—H23B	109.4
C8—C9—H9B	109.3	C22—C23—H23B	109.4
C10—C9—H9B	109.3	H23A—C23—H23B	108.0
H9A—C9—H9B	108.0	C23—C24—C25	110.2 (5)
C11—C10—C9	110.6 (6)	C23—C24—H24A	109.6
C11—C10—H10A	109.5	C25—C24—H24A	109.6
C9—C10—H10A	109.5	C23—C24—H24B	109.6
C11—C10—H10B	109.5	C25—C24—H24B	109.6
C9—C10—H10B	109.5	H24A—C24—H24B	108.1
H10A—C10—H10B	108.1	C26—C25—C24	111.0 (5)
C12—C11—C10	109.3 (6)	C26—C25—H25A	109.4
C12—C11—H11A	109.8	C24—C25—H25A	109.4
C10—C11—H11A	109.8	C26—C25—H25B	109.4
C12—C11—H11B	109.8	C24—C25—H25B	109.4
C10—C11—H11B	109.8	H25A—C25—H25B	108.0
H11A—C11—H11B	108.3	C25—C26—C21	111.6 (5)
C13—C12—C11	110.9 (6)	C25—C26—H26A	109.3
C13—C12—H12A	109.5	C21—C26—H26A	109.3
C11—C12—H12A	109.5	C25—C26—H26B	109.3
C13—C12—H12B	109.5	C21—C26—H26B	109.3
C11—C12—H12B	109.5	H26A—C26—H26B	108.0

Experimental details

Crystal data
Chemical formula	[Ni(C₁₃H₁₅ClNO)₂]
M_r	532.13
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	14.871 (3), 13.563 (3), 24.993 (5)
V (Å³)	5040.9 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.42 × 0.38 × 0.37

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.663, 0.686
No. of measured, independent and observed [I > 2σ(I)] reflections	4933, 4693, 2416
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.162, 1.04
No. of reflections	4693
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.45

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ni1—O1	1.911 (4)	Ni1—N1	2.016 (5)
Ni1—O2	1.911 (4)	Ni1—N2	2.018 (5)

O1—Ni1—O2	120.45 (18)	O1—Ni1—N2	113.09 (19)
O1—Ni1—N1	95.93 (18)	O2—Ni1—N2	94.54 (17)
O2—Ni1—N1	112.44 (18)	N1—Ni1—N2	122.42 (18)

Acknowledgements

The authors appreciate the generous financial support of this work by the Chinese Funds for Zhicheng Project (No. 2006BAC02A11) and Wuhan Yindao project (No. 20066009138-07).

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