Bis{4-chloro-2-[(2-hy­droxy­eth­yl)imino­meth­yl]phenolato}nickel(II) monohydrate

Wang, C.-Y.; Ye, J.-Y.; Wu, X.; Han, Z.-P.

doi:10.1107/S1600536811031680

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1229

doi:10.1107/S1600536811031680

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Bis{4-chloro-2-[(2-hydroxyethyl)iminomethyl]phenolato}nickel(II) monohydrate

Chen-Yi Wang,^a ^* Jin-Yun Ye,^a Xiang Wu ^a and Zhi-Ping Han ^a

^aDepartment of Chemistry, Huzhou University, Huzhou 313000, People's Republic of China
^*Correspondence e-mail: chenyi_wang@163.com

(Received 30 July 2011; accepted 5 August 2011; online 11 August 2011)

The title mononuclear nickel(II) complex, [Ni(C₉H₉ClNO₂)₂]·H₂O, was obtained by the reaction of 5-chlorosalicylaldehyde, 2-aminoethanol and nickel nitrate in methanol. The Ni atom is six-coordinated by two phenolate O, two imine N and two hydroxy O atoms from two crystallographically different Schiff base ligands, forming an octahedral geometry. In the crystal, molecules are linked through intermolecular O—H⋯O and O—H⋯Cl hydrogen bonds.

Related literature

For our investigations of urease inhibitors, see: Wang (2009 ); Wang & Ye (2011 ). For similar nickel(II) complexes, see: Arıcı et al. (2005 ); Liu et al. (2006 ); Li & Wang (2007 ); Ali et al. (2006 ).

Experimental

Crystal data

[Ni(C₉H₉ClNO₂)₂]·H₂O
M_r = 473.97
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.846 (1) Å
b = 12.646 (2) Å
c = 16.006 (2) Å
V = 1992.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.27 mm⁻¹
T = 298 K
0.30 × 0.27 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.701, T_max = 0.725
11691 measured reflections
4328 independent reflections
3147 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.076
S = 1.04
4328 reflections
265 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.39 e Å⁻³
Absolute structure: Flack (1983 ), 1855 Friedel pairs
Flack parameter: 0.015 (15)

Table 1
Selected bond lengths (Å)

Ni1—N2	1.996 (3)
Ni1—N1	2.000 (3)
Ni1—O3	2.011 (2)
Ni1—O1	2.015 (2)
Ni1—O2	2.131 (2)
Ni1—O4	2.160 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯O1ⁱ	0.86 (1)	2.00 (2)	2.846 (4)	167 (4)
O4—H4⋯O5ⁱⁱ	0.85 (1)	1.97 (2)	2.798 (4)	165 (4)
O2—H2⋯O3ⁱⁱⁱ	0.85 (1)	1.87 (2)	2.699 (3)	165 (4)
O5—H5A⋯Cl2	0.84 (1)	2.73 (2)	3.542 (4)	163 (4)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031680/om2456sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031680/om2456Isup2.hkl

checkCIF report

Comment top

As part of our investigations into novel urease inhibitors (Wang & Ye, 2011; Wang, 2009), we have synthesized the title compound, a new mononuclear nickel(II) complex, Fig. 1. The compound contains a mononuclear nickel(II) complex molecule and a water molecule of crystallization. The Ni atom in the complex is six-coordinated by two phenolate O, two imine N, and two hydroxy O atoms from two Schiff base ligands, forming an octahedral geometry. The trans angles at the Ni atom are in the range 172.5 (1)–174.1 (1)°; the other angles are close to 90°, ranging from 80.1 (1) to 94.9 (1)°, indicating a slightly distorted octahedral coordination. The Ni–O and Ni–N bond lengths (Table 1) are typical and are comparable with those observed in other similar nickel(II) complexes (Arıcı et al., 2005; Liu et al., 2006; Li & Wang, 2007; Ali et al., 2006).

In the crystal structure of the compound, molecules are linked through intermolecular O—H···O and O—H···Cl hydrogen bonds (Table 2), to form a three-dimensional network (Fig. 2).

Related literature top

For our investigations of urease inhibitors, see: Wang (2009); Wang & Ye (2011). For similar nickel(II) complexes, see: Arıcı et al. (2005); Liu et al. (2006); Li & Wang (2007); Ali et al. (2006).

Experimental top

5-Chlorosalicylaldehyde (1.0 mmol, 0.157 g), 2-aminoethanol (1.0 mmol, 0.061 g), and nickel nitrate hexahydrate (0.5 mmol, 0.146 g) were dissolved in MeOH (30 ml). The mixture was stirred at room temperature for 10 min to give a clear green solution. After keeping the solution in air for a week, green block-shaped crystals were formed at the bottom of the vessel.

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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The molecular packing of the title compound, viewed along the a axis. Intermolecular hydrogen bonds are shown as dashed lines.

Bis{4-chloro-2-[(2-hydroxyethyl)iminomethyl]phenolato}nickel(II) monohydrate top

Crystal data top

[Ni(C₉H₉ClNO₂)₂]·H₂O	D_x = 1.580 Mg m⁻³
M_r = 473.97	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2792 reflections
a = 9.846 (1) Å	θ = 2.4–24.5°
b = 12.646 (2) Å	µ = 1.27 mm⁻¹
c = 16.006 (2) Å	T = 298 K
V = 1992.9 (4) Å³	Block, green
Z = 4	0.30 × 0.27 × 0.27 mm
F(000) = 976

Data collection top

Bruker SMART CCD area-detector diffractometer	4328 independent reflections
Radiation source: fine-focus sealed tube	3147 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.701, T_max = 0.725	k = −14→16
11691 measured reflections	l = −20→14

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0206P)² + 0.1322P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4328 reflections	Δρ_max = 0.35 e Å⁻³
265 parameters	Δρ_min = −0.39 e Å⁻³
5 restraints	Absolute structure: Flack (1983), 1855 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.015 (15)

Crystal data top

[Ni(C₉H₉ClNO₂)₂]·H₂O	V = 1992.9 (4) Å³
M_r = 473.97	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.846 (1) Å	µ = 1.27 mm⁻¹
b = 12.646 (2) Å	T = 298 K
c = 16.006 (2) Å	0.30 × 0.27 × 0.27 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4328 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3147 reflections with I > 2σ(I)
T_min = 0.701, T_max = 0.725	R_int = 0.048
11691 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.076	Δρ_max = 0.35 e Å⁻³
S = 1.04	Δρ_min = −0.39 e Å⁻³
4328 reflections	Absolute structure: Flack (1983), 1855 Friedel pairs
265 parameters	Absolute structure parameter: 0.015 (15)
5 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. 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	0.53364 (4)	0.24034 (3)	0.09823 (3)	0.03031 (12)
Cl1	−0.07950 (10)	−0.02347 (9)	0.24602 (7)	0.0569 (3)
Cl2	0.4617 (2)	0.80769 (9)	0.02875 (10)	0.1053 (6)
N1	0.4422 (3)	0.1170 (2)	0.04386 (17)	0.0293 (7)
N2	0.6463 (3)	0.3534 (2)	0.15079 (19)	0.0331 (7)
O1	0.3912 (2)	0.2511 (2)	0.18821 (14)	0.0396 (6)
O2	0.6727 (2)	0.21542 (19)	−0.00183 (15)	0.0351 (6)
H2	0.7545 (17)	0.195 (3)	0.000 (3)	0.080*
O3	0.4326 (2)	0.34479 (18)	0.02676 (15)	0.0353 (6)
O4	0.6595 (3)	0.1451 (2)	0.17926 (17)	0.0427 (7)
H4	0.634 (4)	0.0850 (18)	0.198 (3)	0.080*
O5	0.5861 (4)	0.9351 (2)	0.2104 (2)	0.0666 (9)
H5A	0.575 (5)	0.905 (3)	0.1640 (12)	0.080*
H5B	0.601 (4)	0.886 (2)	0.2461 (17)	0.080*
C1	0.2544 (3)	0.1029 (3)	0.1421 (2)	0.0285 (8)
C2	0.2870 (3)	0.1881 (3)	0.1969 (2)	0.0312 (9)
C3	0.1979 (3)	0.2045 (3)	0.2648 (2)	0.0369 (9)
H3	0.2154	0.2602	0.3012	0.044*
C4	0.0863 (4)	0.1416 (3)	0.2794 (2)	0.0385 (9)
H4A	0.0302	0.1547	0.3250	0.046*
C5	0.0581 (3)	0.0591 (3)	0.2259 (2)	0.0377 (10)
C6	0.1391 (3)	0.0405 (3)	0.1584 (2)	0.0353 (9)
H6	0.1177	−0.0147	0.1223	0.042*
C7	0.3306 (3)	0.0749 (3)	0.0684 (2)	0.0317 (9)
H7	0.2953	0.0210	0.0354	0.038*
C8	0.5114 (3)	0.0774 (3)	−0.0304 (2)	0.0376 (9)
H8A	0.4449	0.0547	−0.0714	0.045*
H8B	0.5671	0.0170	−0.0157	0.045*
C9	0.6000 (4)	0.1642 (3)	−0.0674 (2)	0.0409 (10)
H9A	0.6634	0.1339	−0.1071	0.049*
H9B	0.5438	0.2152	−0.0966	0.049*
C10	0.5384 (4)	0.5021 (3)	0.0821 (2)	0.0361 (9)
C11	0.4462 (3)	0.4476 (3)	0.0297 (2)	0.0322 (9)
C12	0.3640 (4)	0.5102 (3)	−0.0228 (2)	0.0398 (10)
H12	0.3043	0.4765	−0.0592	0.048*
C13	0.3680 (4)	0.6183 (3)	−0.0226 (3)	0.0486 (11)
H13	0.3114	0.6569	−0.0578	0.058*
C14	0.4562 (6)	0.6693 (3)	0.0297 (3)	0.0550 (12)
C15	0.5406 (4)	0.6136 (3)	0.0800 (2)	0.0512 (11)
H15	0.6014	0.6498	0.1141	0.061*
C16	0.6327 (4)	0.4522 (3)	0.1399 (2)	0.0395 (10)
H16	0.6877	0.4966	0.1715	0.047*
C17	0.7482 (4)	0.3129 (3)	0.2095 (3)	0.0476 (12)
H17A	0.7642	0.3645	0.2532	0.057*
H17B	0.8331	0.3006	0.1804	0.057*
C18	0.6985 (4)	0.2117 (3)	0.2472 (3)	0.0497 (11)
H18A	0.7699	0.1785	0.2797	0.060*
H18B	0.6215	0.2250	0.2835	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.02362 (18)	0.0263 (2)	0.0410 (3)	−0.0021 (2)	−0.0013 (2)	−0.0026 (2)
Cl1	0.0378 (6)	0.0680 (7)	0.0648 (8)	−0.0153 (5)	0.0081 (6)	0.0168 (6)
Cl2	0.1734 (16)	0.0291 (6)	0.1135 (12)	−0.0054 (9)	−0.0607 (13)	0.0109 (6)
N1	0.0269 (17)	0.0244 (15)	0.0367 (18)	0.0013 (13)	0.0017 (14)	−0.0003 (14)
N2	0.0255 (16)	0.0317 (18)	0.042 (2)	−0.0035 (14)	−0.0052 (14)	0.0019 (15)
O1	0.0363 (12)	0.0363 (14)	0.0463 (15)	−0.0070 (13)	0.0054 (11)	−0.0114 (15)
O2	0.0233 (11)	0.0422 (16)	0.0398 (15)	−0.0034 (11)	0.0018 (12)	−0.0067 (12)
O3	0.0255 (14)	0.0290 (13)	0.0513 (17)	−0.0018 (11)	−0.0073 (12)	−0.0043 (12)
O4	0.0506 (18)	0.0326 (15)	0.0449 (18)	−0.0009 (14)	−0.0107 (15)	0.0006 (14)
O5	0.079 (2)	0.0501 (19)	0.071 (2)	−0.0112 (18)	−0.004 (2)	0.0169 (16)
C1	0.0223 (17)	0.028 (2)	0.035 (2)	−0.0022 (15)	−0.0032 (16)	0.0050 (16)
C2	0.0274 (19)	0.030 (2)	0.036 (2)	−0.0001 (16)	−0.0022 (17)	0.0039 (17)
C3	0.0323 (19)	0.038 (2)	0.041 (3)	0.0041 (16)	−0.0019 (18)	−0.0024 (18)
C4	0.0312 (19)	0.049 (2)	0.035 (2)	0.0061 (19)	0.0062 (17)	0.008 (2)
C5	0.024 (2)	0.042 (2)	0.047 (3)	−0.0032 (17)	−0.0015 (18)	0.0138 (19)
C6	0.0302 (19)	0.038 (2)	0.037 (2)	−0.0020 (17)	−0.0038 (18)	0.0033 (19)
C7	0.0293 (19)	0.0265 (19)	0.039 (2)	−0.0040 (16)	−0.0037 (17)	0.0002 (16)
C8	0.033 (2)	0.041 (2)	0.039 (2)	−0.0057 (17)	0.0062 (17)	−0.0090 (17)
C9	0.036 (2)	0.047 (2)	0.039 (2)	−0.0118 (18)	0.0011 (18)	−0.0060 (19)
C10	0.0386 (19)	0.0278 (18)	0.042 (2)	−0.0028 (18)	−0.003 (2)	0.0008 (16)
C11	0.026 (2)	0.032 (2)	0.039 (2)	−0.0033 (16)	0.0021 (17)	−0.0031 (17)
C12	0.036 (2)	0.037 (2)	0.046 (3)	−0.0033 (18)	−0.0059 (18)	0.003 (2)
C13	0.057 (3)	0.040 (2)	0.049 (3)	0.005 (2)	−0.010 (2)	0.010 (2)
C14	0.086 (3)	0.026 (2)	0.053 (3)	−0.003 (2)	−0.006 (3)	0.0055 (19)
C15	0.068 (3)	0.033 (2)	0.053 (3)	−0.009 (2)	−0.016 (3)	−0.0025 (19)
C16	0.034 (2)	0.031 (2)	0.054 (3)	−0.0088 (17)	−0.0082 (18)	−0.0051 (19)
C17	0.039 (2)	0.043 (2)	0.060 (3)	−0.006 (2)	−0.021 (2)	−0.005 (2)
C18	0.052 (2)	0.043 (3)	0.055 (3)	0.0039 (19)	−0.019 (2)	0.002 (2)

Geometric parameters (Å, º) top

Ni1—N2	1.996 (3)	C4—C5	1.377 (5)
Ni1—N1	2.000 (3)	C4—H4A	0.9300
Ni1—O3	2.011 (2)	C5—C6	1.363 (5)
Ni1—O1	2.015 (2)	C6—H6	0.9300
Ni1—O2	2.131 (2)	C7—H7	0.9300
Ni1—O4	2.160 (3)	C8—C9	1.522 (5)
Cl1—C5	1.741 (3)	C8—H8A	0.9700
Cl2—C14	1.751 (4)	C8—H8B	0.9700
N1—C7	1.283 (4)	C9—H9A	0.9700
N1—C8	1.458 (4)	C9—H9B	0.9700
N2—C16	1.269 (4)	C10—C15	1.410 (5)
N2—C17	1.467 (4)	C10—C11	1.415 (5)
O1—C2	1.307 (4)	C10—C16	1.454 (5)
O2—C9	1.425 (4)	C11—C12	1.410 (5)
O2—H2	0.847 (10)	C12—C13	1.368 (5)
O3—C11	1.308 (4)	C12—H12	0.9300
O4—C18	1.428 (4)	C13—C14	1.367 (5)
O4—H4	0.852 (10)	C13—H13	0.9300
O5—H5B	0.860 (10)	C14—C15	1.355 (5)
O5—H5A	0.844 (10)	C15—H15	0.9300
C1—C6	1.407 (4)	C16—H16	0.9300
C1—C2	1.426 (5)	C17—C18	1.497 (5)
C1—C7	1.442 (5)	C17—H17A	0.9700
C2—C3	1.412 (5)	C17—H17B	0.9700
C3—C4	1.377 (5)	C18—H18A	0.9700
C3—H3	0.9300	C18—H18B	0.9700

N2—Ni1—N1	172.89 (12)	N1—C7—C1	126.4 (3)
N2—Ni1—O3	92.54 (11)	N1—C7—H7	116.8
N1—Ni1—O3	92.40 (10)	C1—C7—H7	116.8
N2—Ni1—O1	92.13 (11)	N1—C8—C9	109.7 (3)
N1—Ni1—O1	92.89 (10)	N1—C8—H8A	109.7
O3—Ni1—O1	91.03 (10)	C9—C8—H8A	109.7
N2—Ni1—O2	93.76 (11)	N1—C8—H8B	109.7
N1—Ni1—O2	81.20 (10)	C9—C8—H8B	109.7
O3—Ni1—O2	89.28 (10)	H8A—C8—H8B	108.2
O1—Ni1—O2	174.08 (10)	O2—C9—C8	109.2 (3)
N2—Ni1—O4	80.06 (11)	O2—C9—H9A	109.8
N1—Ni1—O4	94.87 (11)	C8—C9—H9A	109.8
O3—Ni1—O4	172.50 (10)	O2—C9—H9B	109.8
O1—Ni1—O4	90.43 (10)	C8—C9—H9B	109.8
O2—Ni1—O4	90.02 (10)	H9A—C9—H9B	108.3
C7—N1—C8	120.4 (3)	C15—C10—C11	118.9 (3)
C7—N1—Ni1	125.2 (3)	C15—C10—C16	116.0 (3)
C8—N1—Ni1	114.3 (2)	C11—C10—C16	125.1 (3)
C16—N2—C17	120.3 (3)	O3—C11—C12	118.5 (3)
C16—N2—Ni1	126.0 (3)	O3—C11—C10	124.8 (3)
C17—N2—Ni1	113.6 (2)	C12—C11—C10	116.7 (3)
C2—O1—Ni1	125.6 (2)	C13—C12—C11	122.9 (4)
C9—O2—Ni1	107.31 (19)	C13—C12—H12	118.6
C9—O2—H2	111 (3)	C11—C12—H12	118.6
Ni1—O2—H2	129 (3)	C14—C13—C12	119.4 (4)
C11—O3—Ni1	125.6 (2)	C14—C13—H13	120.3
C18—O4—Ni1	106.4 (2)	C12—C13—H13	120.3
C18—O4—H4	110 (3)	C15—C14—C13	120.6 (4)
Ni1—O4—H4	123 (3)	C15—C14—Cl2	120.4 (4)
H5B—O5—H5A	106 (2)	C13—C14—Cl2	119.0 (4)
C6—C1—C2	119.4 (3)	C14—C15—C10	121.6 (4)
C6—C1—C7	115.7 (3)	C14—C15—H15	119.2
C2—C1—C7	124.9 (3)	C10—C15—H15	119.2
O1—C2—C3	118.7 (3)	N2—C16—C10	125.6 (3)
O1—C2—C1	124.9 (3)	N2—C16—H16	117.2
C3—C2—C1	116.4 (3)	C10—C16—H16	117.2
C4—C3—C2	122.8 (3)	N2—C17—C18	109.5 (3)
C4—C3—H3	118.6	N2—C17—H17A	109.8
C2—C3—H3	118.6	C18—C17—H17A	109.8
C3—C4—C5	119.5 (4)	N2—C17—H17B	109.8
C3—C4—H4A	120.2	C18—C17—H17B	109.8
C5—C4—H4A	120.2	H17A—C17—H17B	108.2
C6—C5—C4	120.4 (3)	O4—C18—C17	106.6 (3)
C6—C5—Cl1	119.9 (3)	O4—C18—H18A	110.4
C4—C5—Cl1	119.8 (3)	C17—C18—H18A	110.4
C5—C6—C1	121.5 (3)	O4—C18—H18B	110.4
C5—C6—H6	119.3	C17—C18—H18B	110.4
C1—C6—H6	119.3	H18A—C18—H18B	108.6

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O1ⁱ	0.86 (1)	2.00 (2)	2.846 (4)	167 (4)
O4—H4···O5ⁱⁱ	0.85 (1)	1.97 (2)	2.798 (4)	165 (4)
O2—H2···O3ⁱⁱⁱ	0.85 (1)	1.87 (2)	2.699 (3)	165 (4)
O5—H5A···Cl2	0.84 (1)	2.73 (2)	3.542 (4)	163 (4)

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

Experimental details

Crystal data
Chemical formula	[Ni(C₉H₉ClNO₂)₂]·H₂O
M_r	473.97
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	9.846 (1), 12.646 (2), 16.006 (2)
V (Å³)	1992.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.27
Crystal size (mm)	0.30 × 0.27 × 0.27

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.701, 0.725
No. of measured, independent and observed [I > 2σ(I)] reflections	11691, 4328, 3147
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.076, 1.04
No. of reflections	4328
No. of parameters	265
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.39
Absolute structure	Flack (1983), 1855 Friedel pairs
Absolute structure parameter	0.015 (15)

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

Selected bond lengths (Å) top

Ni1—N2	1.996 (3)	Ni1—O1	2.015 (2)
Ni1—N1	2.000 (3)	Ni1—O2	2.131 (2)
Ni1—O3	2.011 (2)	Ni1—O4	2.160 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O1ⁱ	0.860 (10)	2.001 (15)	2.846 (4)	167 (4)
O4—H4···O5ⁱⁱ	0.852 (10)	1.965 (16)	2.798 (4)	165 (4)
O2—H2···O3ⁱⁱⁱ	0.847 (10)	1.873 (15)	2.699 (3)	165 (4)
O5—H5A···Cl2	0.844 (10)	2.726 (17)	3.542 (4)	163 (4)

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

Acknowledgements

This work was supported financially by the Natural Science Foundation of China (No. 31071856), the Natural Science Foundation of Zhejiang Province (No. Y407318) and the Applied Research Project on Nonprofit Technology of Zhejiang Province (No. 2010 C32060).

References

Ali, H. M., Puvaneswary, S. & Ng, S. W. (2006). Acta Cryst. E62, m2741–m2742. Web of Science CSD Google Scholar
Arıcı, C., Yüzer, D., Atakol, O., Fuess, H. & Svoboda, I. (2005). Acta Cryst. E61, m919–m921. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Li, L.-Z. & Wang, L.-H. (2007). Acta Cryst. E63, m749–m750. CSD CrossRef IUCr Journals Google Scholar
Liu, X.-H., Cai, J.-H., Jiang, Y.-M., Huang, Y.-H. & Yin, X.-J. (2006). Acta Cryst. E62, m2119–m2121. Web of Science CSD CrossRef IUCr Journals 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
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Volume 67| Part 9| September 2011| Page m1229

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis{4-chloro-2-[(2-hy­dr­oxy­eth­yl)imino­meth­yl]phenolato}nickel(II) monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis{4-chloro-2-[(2-hydroxyethyl)iminomethyl]phenolato}nickel(II) monohydrate