cis-Aqua­bis(2,4-dichloro-6-formyl­phenolato-κ2O,O′)(N,N-dimethyl­formamide-κO)nickel(II)

Chen, F.-Y.; Zhang, S.-H.; Ge, C.-M.

doi:10.1107/S1600536808022939

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page m1068

doi:10.1107/S1600536808022939

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cis-Aquabis(2,4-dichloro-6-formylphenolato-κ²O,O′)(N,N-dimethylformamide-κO)nickel(II)

Fa-Yun Chen,^a Shu-Hua Zhang ^b ^* and Chen-Min Ge ^b

^aDepartment of Chemistry, Shangrao Normal University, Shangrao, Jiangxi 334001, People's Republic of China, and ^bKey Laboratory of Nonferrous Metal Materials and Processing Technology, Department of Materials and Chemical Engineering, Guilin University of Technology, Ministry of Education, Guilin 541004, People's Republic of China
^*Correspondence e-mail: zsh720108@163.com

(Received 15 June 2008; accepted 21 July 2008; online 26 July 2008)

In the title compound, [Ni(C₇H₃Cl₂O₂)₂(C₃H₇NO)(H₂O)], the Ni^II ion is coordinated by four O atoms from two bidentate 2,4-dichloro-6-formylphenolate ligands, one O atom from a water ligand and one O atom from a dimethylformamide ligand in a slightly distorted octahedral environment. In the crystal structure, centrosymmetric dimers are formed though O—H⋯O and O—H⋯Cl hydrogen bonds; π–π stacking interactions, with a centroid–centroid distance of 3.796 (2) Å, are also found.

Related literature

For related literature, see: Cohen et al. (1964 ); Desiraju (1989 ); Mathews & Manohar (1991 ); Zaman et al. (2004 ); Zhang et al. (2007 ); Zordan et al. (2005 ).

Experimental

Crystal data

[Ni(C₇H₃Cl₂O₂)₂(C₃H₇NO)(H₂O)]
M_r = 529.81
Monoclinic, P 2₁ /c
a = 10.404 (2) Å
b = 9.6130 (19) Å
c = 22.161 (4) Å
β = 92.44 (3)°
V = 2214.4 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.39 mm⁻¹
T = 293 (2) K
0.48 × 0.40 × 0.35 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.555, T_max = 0.642
10765 measured reflections
3969 independent reflections
3010 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.111
S = 1.07
3969 reflections
266 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O3	2.041 (2)
Ni1—O1	2.041 (2)
Ni1—O2	2.061 (3)
Ni1—O4	2.070 (3)
Ni1—O5	2.148 (3)
Ni1—O6	2.150 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O1ⁱ	0.82	1.91	2.714 (3)	168
O6—H6B⋯O3ⁱ	0.83 (4)	2.17 (4)	2.850 (4)	139 (4)
O6—H6B⋯Cl3ⁱ	0.84 (4)	2.67 (4)	3.374 (3)	143 (4)
Symmetry code: (i) -x, -y+2, -z+1.

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022939/lh2644sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022939/lh2644Isup2.hkl

checkCIF report

Comment top

Halogens have a ubiquitous presence in both inorganic and organic chemistry. Schiff bases of chloro substituents on aromatic groups have aroused increasing interest in recent years because these halogenated compounds are an attractive target for use in supramolecular chemistry and crystal engineering wherein the halogen atoms are directly involved in forming intermolecular interactions (Cohen et al., 1964; Zordan et al., 2005; Desiraju, 1989; Zaman et al., 2004; Zhang et al., 2007). The title compound, (I), contains the dichloride ligand 3,5-Dichloro-2-hydroxy-benzaldehyde, with two Cl atoms accessible at the periphery of each ligand.

In the molecular structure of (I), the Ni^II ion is coordinated by four O atoms from two bidentate 3,5-Dichloro-2-hydroxy-benzaldehyde ligands, one O atom from a H₂O ligand and one O atom from a N,N'-dimethylformamide ligand forming a slightly distorted octahedral geometry (Fig. 1). In the crystal structure O—H···O and O—H···Cl hydrogen bonds (see Table 2) result in the formation of a centrosymmetric dimer (Fig. 2). Within the dimer, there are π–π stacking interactions between the C1–C6 and C8–C13(-x, 2-y, 1-z) rings with centroid···centroid distance of 3.796 (2) Å and interplanar distance of 3.59 Å giving an offset angle of 3.5°. In the crystal structure, dimers are further linked through weak intermolecular C—H···O hydrogen bonds (Fig. 3) (C5—H5A···O4ⁱⁱ, 3.454 Å, symmetry code: (ii) 1 + x, 2 - y, 1 + z).

Related literature top

For related literature, see: Cohen et al. (1964); Desiraju (1989); Mathews & Manohar (1991); Zaman et al. (2004); Zhang et al. (2007); Zordan et al. (2005).

Experimental top

A ethanol solution (30 ml) containing 3,5-Dichloro-2-hydroxy-benzaldehyde (0.191 g, 1 mmol) was dropwise added to an aqueous solution containing amino-methanesulfonic acid (0.111 g, 1 mmol) and sodium hydroxide (0.040 g, 1 mmol) with stirred during 10 min. After stirring for 1 h, an aqueous solution of Nickel chloride (0.237 g, 1 mmol) was added to the resulting solution and stirred for 2 h. The green solid compound was separated out and dissolved by N,N-Dimethylformamide, then the green solution was filtrated. After 10 days, green crystals were produced from the filtrate (yield: 65.3%, based on Ni).

Computing details top

Data collection: SMART (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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of (I), showing 30% probability displacement ellipsoids. Hydrogen atoms are omitted.
	Fig. 2. The dimer of (I), Dashed lines indicate hydrogen bonds.
	Fig. 3. 1-D chain of (I), Dashed lines indicate hydrogen bonds.

cis-Aquabis(2,4-dichloro-6-formylphenolato-κ²O,O')(N,N-dimethylformamide- κO)nickel(II) top

Crystal data top

[Ni(C₇H₃Cl₂O₂)₂(C₃H₇NO)(H₂O)]	F(000) = 1072
M_r = 529.81	D_x = 1.589 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3969 reflections
a = 10.404 (2) Å	θ = 1.8–25.2°
b = 9.6130 (19) Å	µ = 1.39 mm⁻¹
c = 22.161 (4) Å	T = 293 K
β = 92.44 (3)°	Block, green
V = 2214.4 (8) Å³	0.48 × 0.40 × 0.35 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3969 independent reflections
Radiation source: fine-focus sealed tube	3010 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
Detector resolution: 0 pixels mm^-1	θ_max = 25.2°, θ_min = 1.8°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
T_min = 0.555, T_max = 0.642	l = −23→26
10765 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0455P)² + 2.189P] where P = (F_o² + 2F_c²)/3
3969 reflections	(Δ/σ)_max < 0.001
266 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Ni(C₇H₃Cl₂O₂)₂(C₃H₇NO)(H₂O)]	V = 2214.4 (8) Å³
M_r = 529.81	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.404 (2) Å	µ = 1.39 mm⁻¹
b = 9.6130 (19) Å	T = 293 K
c = 22.161 (4) Å	0.48 × 0.40 × 0.35 mm
β = 92.44 (3)°

Data collection top

Bruker SMART CCD diffractometer	3969 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3010 reflections with I > 2σ(I)
T_min = 0.555, T_max = 0.642	R_int = 0.036
10765 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.59 e Å⁻³
3969 reflections	Δρ_min = −0.37 e Å⁻³
266 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
Ni1	0.20449 (4)	0.95403 (5)	0.46317 (2)	0.03298 (15)
Cl3	−0.19959 (10)	0.74563 (12)	0.37793 (5)	0.0551 (3)
Cl1	0.04788 (11)	0.62415 (13)	0.61561 (5)	0.0620 (3)
Cl4	−0.17775 (12)	1.10954 (17)	0.18744 (5)	0.0754 (4)
Cl2	0.48052 (13)	0.70149 (19)	0.75310 (6)	0.0915 (5)
O2	0.3577 (2)	1.0446 (3)	0.51032 (11)	0.0395 (6)
O1	0.1544 (2)	0.8520 (3)	0.53947 (10)	0.0363 (6)
O4	0.2662 (2)	1.0551 (3)	0.38720 (11)	0.0439 (7)
O6	0.1041 (2)	1.1430 (3)	0.48293 (13)	0.0384 (6)
H6A	0.0272	1.1332	0.4743	0.058*
O3	0.0510 (2)	0.8740 (3)	0.41437 (10)	0.0374 (6)
O5	0.3235 (2)	0.7792 (3)	0.44247 (12)	0.0437 (7)
C1	0.2302 (3)	0.8212 (4)	0.58538 (15)	0.0335 (8)
C7	0.4025 (3)	1.0013 (4)	0.55949 (17)	0.0393 (9)
H7A	0.4775	1.0444	0.5742	0.047*
C8	0.0074 (3)	0.9226 (4)	0.36312 (16)	0.0335 (8)
C9	−0.1159 (3)	0.8770 (4)	0.33844 (16)	0.0381 (9)
C5	0.4263 (4)	0.8523 (5)	0.64989 (17)	0.0485 (11)
H5A	0.5037	0.8981	0.6584	0.058*
C11	−0.1049 (4)	1.0351 (5)	0.25254 (17)	0.0491 (11)
C4	0.3865 (4)	0.7480 (5)	0.68905 (18)	0.0536 (12)
C13	0.0725 (4)	1.0237 (4)	0.32556 (16)	0.0405 (9)
C12	0.0161 (4)	1.0781 (5)	0.27125 (17)	0.0491 (11)
H12A	0.0604	1.1422	0.2486	0.059*
C6	0.3515 (3)	0.8893 (4)	0.59776 (16)	0.0363 (9)
C3	0.2688 (4)	0.6781 (5)	0.67818 (19)	0.0531 (11)
H3A	0.2423	0.6093	0.7044	0.064*
C14	0.2000 (4)	1.0767 (4)	0.34105 (18)	0.0456 (10)
H14A	0.2360	1.1341	0.3125	0.055*
C10	−0.1696 (4)	0.9316 (4)	0.28593 (17)	0.0450 (10)
H10A	−0.2501	0.9005	0.2719	0.054*
C2	0.1946 (4)	0.7137 (4)	0.62829 (18)	0.0424 (9)
N1	0.3665 (4)	0.5364 (4)	0.43658 (16)	0.0520 (9)
C15	0.2951 (4)	0.6490 (5)	0.45053 (17)	0.0454 (10)
H15A	0.2169	0.6310	0.4678	0.054*
C16	0.4864 (5)	0.5594 (6)	0.4064 (3)	0.0785 (16)
H16A	0.5039	0.6574	0.4049	0.118*
H16B	0.4787	0.5230	0.3661	0.118*
H16C	0.5554	0.5131	0.4284	0.118*
C17	0.3215 (7)	0.3854 (5)	0.4433 (3)	0.102 (2)
H17A	0.2417	0.3840	0.4635	0.152*
H17B	0.3852	0.3339	0.4666	0.152*
H17C	0.3093	0.3440	0.4041	0.152*
H6B	0.098 (4)	1.144 (5)	0.5204 (19)	0.053 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0240 (2)	0.0404 (3)	0.0343 (3)	−0.0019 (2)	−0.00076 (18)	0.0032 (2)
Cl3	0.0426 (6)	0.0615 (7)	0.0608 (7)	−0.0183 (5)	−0.0015 (5)	−0.0011 (5)
Cl1	0.0498 (6)	0.0627 (8)	0.0729 (8)	−0.0140 (6)	−0.0032 (5)	0.0246 (6)
Cl4	0.0634 (8)	0.1139 (12)	0.0473 (7)	0.0148 (7)	−0.0164 (6)	0.0139 (7)
Cl2	0.0638 (8)	0.1517 (15)	0.0571 (8)	0.0273 (9)	−0.0192 (6)	0.0263 (8)
O2	0.0269 (13)	0.0485 (16)	0.0427 (15)	−0.0026 (12)	−0.0017 (11)	0.0023 (12)
O1	0.0250 (12)	0.0498 (16)	0.0338 (13)	−0.0039 (11)	−0.0017 (10)	0.0079 (12)
O4	0.0331 (14)	0.0597 (18)	0.0389 (15)	−0.0096 (13)	0.0006 (12)	0.0086 (13)
O6	0.0254 (13)	0.0477 (17)	0.0420 (16)	0.0006 (11)	0.0006 (11)	0.0018 (13)
O3	0.0291 (13)	0.0466 (16)	0.0362 (14)	−0.0065 (11)	−0.0026 (11)	0.0037 (12)
O5	0.0376 (15)	0.0380 (16)	0.0558 (17)	0.0015 (12)	0.0049 (12)	−0.0017 (13)
C1	0.0301 (19)	0.038 (2)	0.0329 (19)	0.0057 (16)	0.0028 (15)	−0.0011 (16)
C7	0.0231 (17)	0.049 (2)	0.046 (2)	−0.0035 (17)	−0.0017 (16)	−0.0043 (19)
C8	0.0279 (18)	0.038 (2)	0.034 (2)	0.0025 (16)	0.0010 (15)	−0.0049 (16)
C9	0.033 (2)	0.041 (2)	0.040 (2)	−0.0006 (17)	0.0021 (16)	−0.0042 (17)
C5	0.031 (2)	0.071 (3)	0.043 (2)	0.010 (2)	−0.0048 (17)	−0.008 (2)
C11	0.042 (2)	0.071 (3)	0.033 (2)	0.010 (2)	−0.0061 (17)	−0.002 (2)
C4	0.042 (2)	0.082 (3)	0.036 (2)	0.018 (2)	−0.0031 (18)	0.007 (2)
C13	0.033 (2)	0.054 (3)	0.035 (2)	−0.0012 (18)	0.0016 (16)	−0.0016 (18)
C12	0.049 (2)	0.059 (3)	0.040 (2)	−0.001 (2)	0.0009 (19)	0.008 (2)
C6	0.0258 (18)	0.047 (2)	0.036 (2)	0.0043 (16)	0.0015 (15)	−0.0056 (17)
C3	0.045 (2)	0.067 (3)	0.047 (2)	0.012 (2)	0.004 (2)	0.016 (2)
C14	0.043 (2)	0.057 (3)	0.038 (2)	−0.011 (2)	0.0053 (18)	0.0128 (19)
C10	0.031 (2)	0.060 (3)	0.044 (2)	0.0008 (19)	−0.0034 (17)	−0.015 (2)
C2	0.038 (2)	0.044 (2)	0.045 (2)	0.0038 (18)	0.0032 (17)	0.0064 (19)
N1	0.056 (2)	0.041 (2)	0.059 (2)	−0.0003 (17)	−0.0052 (18)	−0.0027 (17)
C15	0.040 (2)	0.053 (3)	0.043 (2)	−0.010 (2)	−0.0007 (18)	−0.003 (2)
C16	0.066 (3)	0.075 (4)	0.096 (4)	0.020 (3)	0.015 (3)	−0.009 (3)
C17	0.124 (6)	0.037 (3)	0.142 (6)	−0.015 (3)	−0.008 (5)	0.001 (3)

Geometric parameters (Å, º) top

Ni1—O3	2.041 (2)	C5—C4	1.400 (6)
Ni1—O1	2.041 (2)	C5—C6	1.411 (5)
Ni1—O2	2.061 (3)	C5—H5A	0.9300
Ni1—O4	2.070 (3)	C11—C12	1.372 (6)
Ni1—O5	2.148 (3)	C11—C10	1.426 (6)
Ni1—O6	2.150 (3)	C4—C3	1.408 (6)
Cl3—C9	1.784 (4)	C13—C12	1.416 (5)
Cl1—C2	1.764 (4)	C13—C14	1.448 (5)
Cl4—C11	1.754 (4)	C12—H12A	0.9300
Cl2—C4	1.748 (4)	C3—C2	1.365 (5)
O2—C7	1.239 (4)	C3—H3A	0.9300
O1—C1	1.295 (4)	C14—H14A	0.9300
O4—C14	1.226 (4)	C10—H10A	0.9300
O6—H6A	0.8200	N1—C15	1.356 (5)
O6—H6B	0.83 (4)	N1—C16	1.456 (6)
O3—C8	1.292 (4)	N1—C17	1.534 (6)
O5—C15	1.301 (5)	C15—H15A	0.9300
C1—C6	1.437 (5)	C16—H16A	0.9600
C1—C2	1.463 (5)	C16—H16B	0.9600
C7—C6	1.483 (5)	C16—H16C	0.9600
C7—H7A	0.9300	C17—H17A	0.9600
C8—C9	1.441 (5)	C17—H17B	0.9600
C8—C13	1.465 (5)	C17—H17C	0.9600
C9—C10	1.374 (5)

O3—Ni1—O1	92.08 (10)	C5—C4—Cl2	121.1 (4)
O3—Ni1—O2	177.03 (10)	C3—C4—Cl2	118.0 (3)
O1—Ni1—O2	90.12 (10)	C12—C13—C14	114.5 (4)
O3—Ni1—O4	90.51 (10)	C12—C13—C8	122.9 (3)
O1—Ni1—O4	176.71 (10)	C14—C13—C8	122.7 (3)
O2—Ni1—O4	87.36 (10)	C11—C12—C13	119.2 (4)
O3—Ni1—O5	92.13 (10)	C11—C12—H12A	120.4
O1—Ni1—O5	88.33 (10)	C13—C12—H12A	120.4
O2—Ni1—O5	89.92 (10)	C5—C6—C1	119.4 (4)
O4—Ni1—O5	89.55 (11)	C5—C6—C7	116.9 (3)
O3—Ni1—O6	92.88 (10)	C1—C6—C7	123.7 (3)
O1—Ni1—O6	95.38 (10)	C2—C3—C4	118.5 (4)
O2—Ni1—O6	84.93 (10)	C2—C3—H3A	120.8
O4—Ni1—O6	86.51 (11)	C4—C3—H3A	120.8
O5—Ni1—O6	173.65 (10)	O4—C14—C13	127.9 (4)
C7—O2—Ni1	123.9 (2)	O4—C14—H14A	116.0
C1—O1—Ni1	126.3 (2)	C13—C14—H14A	116.0
C14—O4—Ni1	125.1 (2)	C9—C10—C11	121.5 (4)
Ni1—O6—H6A	109.5	C9—C10—H10A	119.3
Ni1—O6—H6B	106 (3)	C11—C10—H10A	119.3
H6A—O6—H6B	96.5	C3—C2—C1	123.6 (4)
C8—O3—Ni1	124.5 (2)	C3—C2—Cl1	117.6 (3)
C15—O5—Ni1	126.0 (2)	C1—C2—Cl1	118.9 (3)
O1—C1—C6	123.1 (3)	C15—N1—C16	118.1 (4)
O1—C1—C2	120.6 (3)	C15—N1—C17	124.0 (4)
C6—C1—C2	116.3 (3)	C16—N1—C17	117.4 (4)
O2—C7—C6	128.0 (3)	O5—C15—N1	127.4 (4)
O2—C7—H7A	116.0	O5—C15—H15A	116.3
C6—C7—H7A	116.0	N1—C15—H15A	116.3
O3—C8—C9	119.8 (3)	N1—C16—H16A	109.5
O3—C8—C13	125.9 (3)	N1—C16—H16B	109.5
C9—C8—C13	114.4 (3)	H16A—C16—H16B	109.5
C10—C9—C8	121.9 (4)	N1—C16—H16C	109.5
C10—C9—Cl3	119.8 (3)	H16A—C16—H16C	109.5
C8—C9—Cl3	118.3 (3)	H16B—C16—H16C	109.5
C4—C5—C6	121.4 (4)	N1—C17—H17A	109.5
C4—C5—H5A	119.3	N1—C17—H17B	109.5
C6—C5—H5A	119.3	H17A—C17—H17B	109.5
C12—C11—C10	120.1 (4)	N1—C17—H17C	109.5
C12—C11—Cl4	119.0 (3)	H17A—C17—H17C	109.5
C10—C11—Cl4	120.9 (3)	H17B—C17—H17C	109.5
C5—C4—C3	120.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O1ⁱ	0.82	1.91	2.714 (3)	168
O6—H6B···O3ⁱ	0.83 (4)	2.17 (4)	2.850 (4)	139 (4)
O6—H6B···Cl3ⁱ	0.84 (4)	2.67 (4)	3.374 (3)	143 (4)

Symmetry code: (i) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₇H₃Cl₂O₂)₂(C₃H₇NO)(H₂O)]
M_r	529.81
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.404 (2), 9.6130 (19), 22.161 (4)
β (°)	92.44 (3)
V (Å³)	2214.4 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.39
Crystal size (mm)	0.48 × 0.40 × 0.35

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.555, 0.642
No. of measured, independent and observed [I > 2σ(I)] reflections	10765, 3969, 3010
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.111, 1.07
No. of reflections	3969
No. of parameters	266
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.37

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ni1—O3	2.041 (2)	Ni1—O4	2.070 (3)
Ni1—O1	2.041 (2)	Ni1—O5	2.148 (3)
Ni1—O2	2.061 (3)	Ni1—O6	2.150 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O1ⁱ	0.82	1.91	2.714 (3)	168.3
O6—H6B···O3ⁱ	0.83 (4)	2.17 (4)	2.850 (4)	139 (4)
O6—H6B···Cl3ⁱ	0.84 (4)	2.67 (4)	3.374 (3)	143 (4)

Symmetry code: (i) −x, −y+2, −z+1.

Acknowledgements

The authors acknowledge financial support from the Natural Science Foundation of Guangxi Province, China (grant No. 0832085).

References

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