Bis{4-chloro-2-[(2-hy-droxy-eth-yl)imino-meth-yl]phenolato}nickel(II) monohydrate.

The title mononuclear nickel(II) complex, [Ni(C(9)H(9)ClNO(2))(2)]·H(2)O, was obtained by the reaction of 5-chloro-salicyl-aldehyde, 2-amino-ethanol and nickel nitrate in methanol. The Ni atom is six-coordinated by two phenolate O, two imine N and two hy-droxy O atoms from two crystallographically different Schiff base ligands, forming an octa-hedral geometry. In the crystal, mol-ecules are linked through inter-molecular 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 = 473.97

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.076

S = 1.04

4328 reflections

265 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.39 e Å−3

Absolute structure: Flack (1983 ▶), 1855 Friedel pairs

Flack parameter: 0.015 (15)

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031680/om2456sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C9H9ClNO2)2]·H2O	Dx = 1.580 Mg m−3
Mr = 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

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

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(Fo2) + (0.0206P)2 + 0.1322P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
4328 reflections	Δρmax = 0.35 e Å−3
265 parameters	Δρmin = −0.39 e Å−3
5 restraints	Absolute structure: Flack (1983), 1855 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.015 (15)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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)

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) ; (ii) ; (iii) .