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

Wang, C.-Y.; Li, J.-F.; Wang, P.; Yuan, C.-J.

doi:10.1107/S1600536811031771

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages m1227-m1228

doi:10.1107/S1600536811031771

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

Chen-Yi Wang,^a ^* Jing-Fen Li,^a Ping Wang ^b and Cai-Jun Yuan ^a

^aDepartment of Chemistry, Huzhou University, Huzhou 313000, People's Republic of China, and ^bCollege of Chemical Engineering, Nanjing Forestry University, Nangjing 210037, People's Republic of China
^*Correspondence e-mail: chenyi_wang@163.com

(Received 28 July 2011; accepted 5 August 2011; online 11 August 2011)

The title mononuclear nickel complex, [Ni(C₉H₉BrNO₂)₂]·H₂O, was obtained by the reaction of 5-bromosalicylaldehyde, 2-aminoethanol and nickel nitrate in methanol. The Ni^II 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 by intermolecular O—H⋯O and O—H⋯Br hydrogen bonds, forming a three-dimensional network.

Related literature

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

Experimental

Crystal data

[Ni(C₉H₉BrNO₂)₂]·H₂O
M_r = 562.89
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.835 (3) Å
b = 12.851 (2) Å
c = 16.226 (3) Å
V = 2050.8 (8) Å³
Z = 4
Mo Kα radiation
μ = 4.87 mm⁻¹
T = 298 K
0.21 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.428, T_max = 0.442
13318 measured reflections
4474 independent reflections
2310 reflections with I > 2σ(I)
R_int = 0.099

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.128
S = 1.02
4474 reflections
259 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.95 e Å⁻³
Absolute structure: Flack (1983 ), 1930 Friedel pairs
Flack parameter: 0.013 (19)

Table 1
Selected bond lengths (Å)

Ni1—N1	1.976 (7)
Ni1—N2	1.981 (7)
Ni1—O1	2.008 (6)
Ni1—O3	2.014 (6)
Ni1—O2	2.132 (5)
Ni1—O4	2.160 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯O1	0.85 (1)	2.22 (7)	2.898 (8)	136 (8)
O5—H5A⋯Br2ⁱ	0.85 (1)	2.92 (5)	3.666 (9)	146 (8)
O4—H4A⋯Br1ⁱⁱ	0.93	2.90	3.532 (6)	126
O4—H4A⋯O5ⁱ	0.93	2.16	2.841 (9)	130
O2—H2A⋯O3ⁱⁱⁱ	0.93	1.97	2.694 (7)	133
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811031771/ci5196sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031771/ci5196Isup2.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 173.1 (3)–174.0 (2)°; the other angles are close to 90°, ranging from 80.4 (3) to 94.8 (2)°, indicating a slightly distorted octahedral coordination. The Ni—O and Ni—N bond lengths (Table 1) are typical and are comparable to 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···Br hydrogen bonds (Table 2), to form a three-dimensional network (Fig. 2).

Related literature top

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

Experimental top

5-Bromosalicylaldehyde (1.0 mmol, 0.201 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: SHELXTL (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. The dashed line indicates a hydrogen bond.
	Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

[Ni(C₉H₉BrNO₂)₂]·H₂O	F(000) = 1120
M_r = 562.89	D_x = 1.823 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2063 reflections
a = 9.835 (3) Å	θ = 2.5–25.3°
b = 12.851 (2) Å	µ = 4.87 mm⁻¹
c = 16.226 (3) Å	T = 298 K
V = 2050.8 (8) Å³	BlocK, green
Z = 4	0.21 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4474 independent reflections
Radiation source: fine-focus sealed tube	2310 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.428, T_max = 0.442	k = −16→16
13318 measured reflections	l = −20→15

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0374P)² + 1.9512P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
4474 reflections	Δρ_max = 0.60 e Å⁻³
259 parameters	Δρ_min = −0.95 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 1930 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.013 (19)

Crystal data top

[Ni(C₉H₉BrNO₂)₂]·H₂O	V = 2050.8 (8) Å³
M_r = 562.89	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.835 (3) Å	µ = 4.87 mm⁻¹
b = 12.851 (2) Å	T = 298 K
c = 16.226 (3) Å	0.21 × 0.20 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4474 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2310 reflections with I > 2σ(I)
T_min = 0.428, T_max = 0.442	R_int = 0.099
13318 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.128	Δρ_max = 0.60 e Å⁻³
S = 1.02	Δρ_min = −0.95 e Å⁻³
4474 reflections	Absolute structure: Flack (1983), 1930 Friedel pairs
259 parameters	Absolute structure parameter: 0.013 (19)
3 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
Br1	1.08191 (9)	−0.02277 (7)	0.25079 (7)	0.0550 (3)
Br2	0.5363 (2)	0.81053 (8)	0.47258 (10)	0.1150 (7)
Ni1	0.45998 (10)	0.24321 (8)	0.40117 (7)	0.0323 (3)
O1	0.6019 (5)	0.2555 (4)	0.3127 (4)	0.0425 (15)
O2	0.3198 (5)	0.2157 (4)	0.4990 (3)	0.0364 (16)
H2A	0.2280	0.2329	0.4989	0.044*
O3	0.5614 (6)	0.3443 (4)	0.4733 (4)	0.0366 (15)
O4	0.3367 (6)	0.1508 (4)	0.3188 (4)	0.0451 (17)
H4A	0.3131	0.0812	0.3251	0.054*
O5	0.5810 (10)	0.4431 (5)	0.2144 (5)	0.074 (2)
N1	0.5494 (7)	0.1225 (5)	0.4536 (4)	0.0307 (17)
N2	0.3496 (7)	0.3550 (5)	0.3502 (5)	0.0371 (19)
C1	0.7389 (8)	0.1086 (6)	0.3572 (5)	0.029 (2)
C2	0.7047 (8)	0.1925 (6)	0.3039 (5)	0.032 (2)
C3	0.7945 (8)	0.2085 (6)	0.2369 (6)	0.040 (2)
H3	0.7772	0.2640	0.2016	0.048*
C4	0.9041 (9)	0.1480 (7)	0.2209 (6)	0.042 (2)
H4	0.9582	0.1617	0.1752	0.051*
C5	0.9358 (9)	0.0658 (7)	0.2726 (6)	0.042 (2)
C6	0.8539 (8)	0.0483 (6)	0.3384 (6)	0.038 (2)
H6	0.8751	−0.0070	0.3732	0.046*
C7	0.6629 (8)	0.0814 (6)	0.4292 (5)	0.028 (2)
H7	0.6986	0.0286	0.4620	0.033*
C8	0.4827 (8)	0.0827 (6)	0.5276 (5)	0.040 (2)
H8A	0.5507	0.0620	0.5676	0.047*
H8B	0.4287	0.0220	0.5138	0.047*
C9	0.3914 (9)	0.1664 (7)	0.5646 (6)	0.045 (3)
H9A	0.3276	0.1353	0.6030	0.054*
H9B	0.4458	0.2171	0.5941	0.054*
C10	0.4558 (9)	0.5003 (6)	0.4176 (5)	0.041 (2)
C11	0.5478 (8)	0.4458 (6)	0.4704 (5)	0.033 (2)
C12	0.6275 (8)	0.5055 (6)	0.5233 (6)	0.045 (2)
H12	0.6845	0.4714	0.5602	0.055*
C13	0.6258 (10)	0.6126 (7)	0.5234 (6)	0.051 (3)
H13	0.6819	0.6502	0.5586	0.061*
C14	0.5408 (13)	0.6614 (7)	0.4712 (7)	0.060 (3)
C15	0.4569 (12)	0.6097 (7)	0.4200 (7)	0.062 (3)
H15	0.3987	0.6469	0.3857	0.075*
C16	0.3650 (8)	0.4525 (6)	0.3608 (6)	0.041 (2)
H16	0.3121	0.4964	0.3285	0.049*
C17	0.2488 (9)	0.3159 (7)	0.2904 (6)	0.051 (3)
H17A	0.2340	0.3675	0.2477	0.061*
H17B	0.1628	0.3033	0.3180	0.061*
C18	0.2992 (9)	0.2178 (6)	0.2530 (7)	0.051 (3)
H18A	0.2286	0.1858	0.2198	0.062*
H18B	0.3771	0.2316	0.2180	0.062*
H5A	0.584 (12)	0.395 (5)	0.178 (4)	0.080*
H5B	0.605 (11)	0.415 (6)	0.260 (3)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0343 (4)	0.0641 (6)	0.0666 (7)	0.0118 (5)	0.0052 (6)	−0.0190 (6)
Br2	0.2030 (18)	0.0286 (5)	0.1133 (12)	0.0049 (9)	−0.0640 (13)	−0.0095 (7)
Ni1	0.0245 (5)	0.0278 (5)	0.0446 (7)	0.0024 (5)	0.0003 (5)	0.0031 (5)
O1	0.032 (3)	0.036 (3)	0.059 (4)	0.013 (3)	0.003 (3)	0.011 (3)
O2	0.026 (3)	0.038 (4)	0.045 (4)	0.015 (3)	−0.003 (3)	0.004 (3)
O3	0.030 (4)	0.032 (3)	0.048 (4)	0.001 (3)	−0.006 (3)	0.009 (3)
O4	0.051 (4)	0.035 (3)	0.050 (5)	−0.003 (3)	−0.012 (4)	0.001 (3)
O5	0.076 (5)	0.062 (4)	0.083 (6)	−0.010 (5)	0.002 (5)	0.017 (4)
N1	0.031 (4)	0.025 (3)	0.036 (5)	−0.005 (3)	0.008 (4)	0.000 (3)
N2	0.027 (4)	0.034 (4)	0.050 (5)	−0.005 (3)	−0.002 (4)	−0.005 (4)
C1	0.026 (5)	0.031 (5)	0.029 (6)	0.008 (4)	0.001 (4)	−0.012 (4)
C2	0.030 (5)	0.024 (4)	0.041 (6)	0.000 (4)	−0.006 (5)	−0.002 (4)
C3	0.043 (5)	0.034 (5)	0.044 (7)	−0.002 (4)	0.000 (5)	0.004 (5)
C4	0.029 (5)	0.060 (6)	0.037 (6)	−0.011 (5)	0.013 (4)	−0.006 (5)
C5	0.034 (5)	0.045 (5)	0.046 (7)	−0.007 (4)	0.001 (5)	−0.022 (5)
C6	0.027 (5)	0.033 (5)	0.055 (7)	0.006 (4)	0.007 (5)	−0.012 (5)
C7	0.026 (5)	0.019 (4)	0.038 (6)	0.007 (3)	−0.005 (4)	−0.006 (4)
C8	0.036 (5)	0.043 (5)	0.039 (6)	0.001 (4)	0.002 (5)	0.012 (5)
C9	0.031 (5)	0.058 (6)	0.045 (7)	0.013 (4)	0.007 (5)	−0.008 (5)
C10	0.043 (5)	0.034 (4)	0.048 (6)	0.004 (4)	−0.008 (5)	0.000 (4)
C11	0.027 (5)	0.035 (5)	0.036 (6)	−0.001 (4)	−0.008 (5)	0.001 (4)
C12	0.046 (6)	0.038 (5)	0.052 (7)	0.007 (4)	−0.009 (5)	−0.001 (5)
C13	0.057 (7)	0.037 (5)	0.059 (8)	−0.001 (5)	−0.009 (6)	−0.016 (5)
C14	0.080 (8)	0.031 (5)	0.067 (8)	−0.001 (6)	−0.008 (8)	0.001 (5)
C15	0.077 (7)	0.037 (5)	0.073 (8)	0.013 (6)	−0.018 (7)	−0.004 (5)
C16	0.036 (5)	0.029 (5)	0.057 (7)	0.004 (4)	−0.018 (5)	0.002 (5)
C17	0.040 (6)	0.040 (5)	0.072 (8)	0.012 (5)	−0.008 (5)	0.011 (5)
C18	0.048 (5)	0.053 (6)	0.053 (7)	−0.002 (4)	−0.020 (6)	0.000 (6)

Geometric parameters (Å, º) top

Ni1—N1	1.976 (7)	C4—C5	1.385 (12)
Ni1—N2	1.981 (7)	C4—H4	0.93
Ni1—O1	2.008 (6)	C5—C6	1.356 (11)
Ni1—O3	2.014 (6)	C6—H6	0.93
Ni1—O2	2.132 (5)	C7—H7	0.93
Ni1—O4	2.160 (6)	C8—C9	1.523 (11)
Br1—C5	1.867 (9)	C8—H8A	0.97
Br2—C14	1.917 (8)	C8—H8B	0.97
O1—C2	1.303 (9)	C9—H9A	0.97
O2—C9	1.424 (10)	C9—H9B	0.97
O2—H2A	0.9298	C10—C15	1.407 (12)
O3—C11	1.312 (8)	C10—C16	1.423 (11)
O4—C18	1.420 (10)	C10—C11	1.430 (11)
O4—H4A	0.9298	C11—C12	1.392 (11)
O5—H5A	0.853 (10)	C12—C13	1.377 (11)
O5—H5B	0.854 (10)	C12—H12	0.93
N1—C7	1.297 (10)	C13—C14	1.346 (13)
N1—C8	1.461 (10)	C13—H13	0.93
N2—C16	1.274 (10)	C14—C15	1.346 (14)
N2—C17	1.476 (11)	C15—H15	0.93
C1—C6	1.405 (10)	C16—H16	0.93
C1—C2	1.422 (11)	C17—C18	1.485 (12)
C1—C7	1.431 (11)	C17—H17A	0.97
C2—C3	1.416 (12)	C17—H17B	0.97
C3—C4	1.354 (11)	C18—H18A	0.97
C3—H3	0.93	C18—H18B	0.97

N1—Ni1—N2	173.1 (3)	N1—C7—C1	126.8 (8)
N1—Ni1—O1	93.4 (2)	N1—C7—H7	116.6
N2—Ni1—O1	91.5 (3)	C1—C7—H7	116.6
N1—Ni1—O3	92.1 (2)	N1—C8—C9	110.0 (7)
N2—Ni1—O3	92.6 (2)	N1—C8—H8A	109.7
O1—Ni1—O3	91.2 (2)	C9—C8—H8A	109.7
N1—Ni1—O2	80.6 (2)	N1—C8—H8B	109.7
N2—Ni1—O2	94.4 (3)	C9—C8—H8B	109.7
O1—Ni1—O2	174.0 (2)	H8A—C8—H8B	108.2
O3—Ni1—O2	89.7 (2)	O2—C9—C8	108.1 (7)
N1—Ni1—O4	94.8 (2)	O2—C9—H9A	110.1
N2—Ni1—O4	80.4 (3)	C8—C9—H9A	110.1
O1—Ni1—O4	89.5 (2)	O2—C9—H9B	110.1
O3—Ni1—O4	173.0 (2)	C8—C9—H9B	110.1
O2—Ni1—O4	90.4 (2)	H9A—C9—H9B	108.4
C2—O1—Ni1	124.7 (5)	C15—C10—C16	117.0 (8)
C9—O2—Ni1	108.1 (5)	C15—C10—C11	117.9 (8)
C9—O2—H2A	126.0	C16—C10—C11	125.0 (7)
Ni1—O2—H2A	125.9	O3—C11—C12	117.9 (7)
C11—O3—Ni1	124.8 (5)	O3—C11—C10	125.0 (7)
C18—O4—Ni1	106.1 (5)	C12—C11—C10	117.1 (7)
C18—O4—H4A	126.9	C13—C12—C11	123.0 (8)
Ni1—O4—H4A	126.9	C13—C12—H12	118.5
H5A—O5—H5B	106 (3)	C11—C12—H12	118.5
C7—N1—C8	119.7 (7)	C14—C13—C12	118.2 (9)
C7—N1—Ni1	124.9 (6)	C14—C13—H13	120.9
C8—N1—Ni1	115.4 (5)	C12—C13—H13	120.9
C16—N2—C17	120.2 (8)	C13—C14—C15	122.6 (9)
C16—N2—Ni1	126.3 (6)	C13—C14—Br2	118.3 (8)
C17—N2—Ni1	113.3 (5)	C15—C14—Br2	119.1 (8)
C6—C1—C2	118.5 (8)	C14—C15—C10	121.0 (9)
C6—C1—C7	117.5 (8)	C14—C15—H15	119.5
C2—C1—C7	123.9 (7)	C10—C15—H15	119.5
O1—C2—C3	118.5 (7)	N2—C16—C10	125.9 (8)
O1—C2—C1	126.0 (8)	N2—C16—H16	117.0
C3—C2—C1	115.4 (7)	C10—C16—H16	117.0
C4—C3—C2	124.0 (8)	N2—C17—C18	109.5 (7)
C4—C3—H3	118.0	N2—C17—H17A	109.8
C2—C3—H3	118.0	C18—C17—H17A	109.8
C3—C4—C5	120.1 (9)	N2—C17—H17B	109.8
C3—C4—H4	119.9	C18—C17—H17B	109.8
C5—C4—H4	119.9	H17A—C17—H17B	108.2
C6—C5—C4	118.0 (8)	O4—C18—C17	107.1 (8)
C6—C5—Br1	120.3 (7)	O4—C18—H18A	110.3
C4—C5—Br1	121.6 (7)	C17—C18—H18A	110.3
C5—C6—C1	123.8 (9)	O4—C18—H18B	110.3
C5—C6—H6	118.1	C17—C18—H18B	110.3
C1—C6—H6	118.1	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···O1	0.85 (1)	2.22 (7)	2.898 (8)	136 (8)
O5—H5A···Br2ⁱ	0.85 (1)	2.92 (5)	3.666 (9)	146 (8)
O4—H4A···Br1ⁱⁱ	0.93	2.90	3.532 (6)	126
O4—H4A···O5ⁱ	0.93	2.16	2.841 (9)	130
O2—H2A···O3ⁱⁱⁱ	0.93	1.97	2.694 (7)	133

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

Experimental details

Crystal data
Chemical formula	[Ni(C₉H₉BrNO₂)₂]·H₂O
M_r	562.89
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	9.835 (3), 12.851 (2), 16.226 (3)
V (Å³)	2050.8 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.87
Crystal size (mm)	0.21 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.428, 0.442
No. of measured, independent and observed [I > 2σ(I)] reflections	13318, 4474, 2310
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.128, 1.02
No. of reflections	4474
No. of parameters	259
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.95
Absolute structure	Flack (1983), 1930 Friedel pairs
Absolute structure parameter	0.013 (19)

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

Selected bond lengths (Å) top

Ni1—N1	1.976 (7)	Ni1—O3	2.014 (6)
Ni1—N2	1.981 (7)	Ni1—O2	2.132 (5)
Ni1—O1	2.008 (6)	Ni1—O4	2.160 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O1	0.85 (1)	2.22 (7)	2.898 (8)	136 (8)
O5—H5A···Br2ⁱ	0.85 (1)	2.92 (5)	3.666 (9)	146 (8)
O4—H4A···Br1ⁱⁱ	0.93	2.90	3.532 (6)	126
O4—H4A···O5ⁱ	0.93	2.16	2.841 (9)	130
O2—H2A···O3ⁱⁱⁱ	0.93	1.97	2.694 (7)	133

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

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
Wang, C.-Y. (2009). J. Coord. Chem. 62, 2860–2868. Web of Science CSD CrossRef CAS Google Scholar
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Volume 67| Part 9| September 2011| Pages m1227-m1228

doi:10.1107/S1600536811031771

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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