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

The title mononuclear nickel complex, [Ni(C(9)H(9)BrNO(2))(2)]·H(2)O, was obtained by the reaction of 5-bromo-salicyl-aldehyde, 2-amino-ethanol and nickel nitrate in methanol. The Ni(II) 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 by inter-molecular 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 = 562.89

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.128

S = 1.02

4474 reflections

259 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.60 e Å−3

Δρmin = −0.95 e Å−3

Absolute structure: Flack (1983 ▶), 1930 Friedel pairs

Flack parameter: 0.013 (19)

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031771/ci5196sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031771/ci5196Isup2.hkl

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

[Ni(C9H9BrNO2)2]·H2O	F(000) = 1120
Mr = 562.89	Dx = 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

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

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(Fo2) + (0.0374P)2 + 1.9512P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4474 reflections	Δρmax = 0.60 e Å−3
259 parameters	Δρmin = −0.95 e Å−3
3 restraints	Absolute structure: Flack (1983), 1930 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.013 (19)

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
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*

	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)

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

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

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) ; (ii) ; (iii) .