Dibromido{2-[2-(piperidinium-1-yl)ethyl-imino-meth-yl]phenolato}zinc(II) monohydrate.

The asymmetric unit of the title compound, [ZnBr(2)(C(14)H(20)N(2)O)]·H(2)O, consists of a mononuclear Schiff base zinc(II) complex mol-ecule and a solvent water mol-ecule. The Zn(II) atom is four-coordinated in an approximately tetra-hedral geometry, binding to the imine N and phenolate O atoms of the neutral zwitterionic Schiff base ligand and to two terminal Br(-) anions. In the crystal structure, mol-ecules are linked through inter-molecular O-H⋯Br and O-H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For the background to Schiff base zinc(II) complexes, see: Bhosekar et al. (2006 ▶); Chisholm et al. (2001 ▶); Jian et al. (2004 ▶); Lacroix et al. (1996 ▶); Tatar et al. (2002 ▶). For related structures, see: Ma, Gu et al. (2006 ▶); Ma, Lv et al. (2006 ▶); Peng & Hou (2006 ▶); Peng et al. (2006 ▶); Wei et al. (2007 ▶); Zhang et al. (2008 ▶); Zhu et al. (2007 ▶).

Experimental

Crystal data

[ZnBr2(C14H20N2O)]·H2O

M = 475.53

Triclinic,

a = 9.2997 (18) Å

b = 10.1776 (17) Å

c = 11.1667 (18) Å

α = 71.510 (2)°

β = 71.215 (2)°

γ = 67.571 (2)°

V = 901.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 5.80 mm−1

T = 298 (2) K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.390, T max = 0.422 (expected range = 0.326–0.352)

5468 measured reflections

3983 independent reflections

2891 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.091

S = 1.02

3983 reflections

199 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.72 e Å−3

Δρmin = −0.55 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536808015730/sj2508sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015730/sj2508Isup2.hkl

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

[ZnBr2(C14H20N2O)]·H2O	Z = 2
Mr = 475.53	F000 = 472
Triclinic, P1	Dx = 1.751 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.2997 (18) Å	Cell parameters from 1797 reflections
b = 10.1776 (17) Å	θ = 2.2–25.4º
c = 11.1667 (18) Å	µ = 5.80 mm−1
α = 71.510 (2)º	T = 298 (2) K
β = 71.215 (2)º	Block, yellow
γ = 67.571 (2)º	0.20 × 0.20 × 0.18 mm
V = 901.8 (3) Å3

Bruker SMART 1000 CCD area-detector diffractometer	3983 independent reflections
Radiation source: fine-focus sealed tube	2891 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.016
T = 298(2) K	θmax = 27.5º
ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −12→9
Tmin = 0.390, Tmax = 0.422	k = −13→12
5468 measured reflections	l = −14→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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0405P)2 + 0.3508P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3983 reflections	Δρmax = 0.72 e Å−3
199 parameters	Δρmin = −0.55 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
Zn1	0.82333 (5)	−0.20793 (4)	0.11443 (4)	0.03909 (13)
Br1	0.93736 (6)	−0.24561 (5)	0.28619 (4)	0.06059 (15)
Br2	0.56849 (5)	−0.24885 (5)	0.18395 (4)	0.05682 (14)
O1	0.9582 (3)	−0.3089 (3)	−0.0226 (2)	0.0451 (6)
O2	0.7190 (3)	0.4568 (3)	0.0481 (3)	0.0515 (7)
N1	0.8013 (4)	−0.0074 (3)	−0.0039 (3)	0.0406 (7)
N2	0.5644 (4)	0.2574 (3)	0.2120 (3)	0.0420 (7)
C1	0.8738 (4)	−0.1069 (4)	−0.1951 (3)	0.0378 (8)
C2	0.9415 (4)	−0.2555 (4)	−0.1434 (3)	0.0379 (8)
C3	0.9993 (5)	−0.3518 (4)	−0.2277 (4)	0.0451 (9)
H3	1.0451	−0.4508	−0.1960	0.054*
C4	0.9897 (5)	−0.3031 (5)	−0.3550 (4)	0.0555 (11)
H4	1.0283	−0.3696	−0.4077	0.067*
C5	0.9234 (6)	−0.1561 (5)	−0.4069 (4)	0.0594 (12)
H5	0.9176	−0.1236	−0.4935	0.071*
C6	0.8668 (5)	−0.0600 (5)	−0.3273 (4)	0.0513 (10)
H6	0.8225	0.0387	−0.3611	0.062*
C7	0.8178 (4)	0.0091 (4)	−0.1258 (4)	0.0409 (8)
H7	0.7915	0.1043	−0.1745	0.049*
C8	0.7581 (5)	0.1241 (4)	0.0443 (4)	0.0552 (11)
H8A	0.7560	0.2080	−0.0279	0.066*
H8B	0.8374	0.1140	0.0884	0.066*
C9	0.5982 (5)	0.1467 (5)	0.1357 (5)	0.0633 (12)
H9A	0.5928	0.0547	0.1952	0.076*
H9B	0.5166	0.1790	0.0870	0.076*
C10	0.3889 (5)	0.3298 (5)	0.2454 (5)	0.0594 (11)
H10A	0.3359	0.2573	0.2962	0.071*
H10B	0.3502	0.3761	0.1664	0.071*
C11	0.3486 (6)	0.4435 (6)	0.3223 (6)	0.0836 (17)
H11A	0.3915	0.5216	0.2677	0.100*
H11B	0.2334	0.4848	0.3476	0.100*
C12	0.4153 (7)	0.3795 (7)	0.4409 (6)	0.094 (2)
H12A	0.3925	0.4556	0.4853	0.113*
H12B	0.3651	0.3077	0.4997	0.113*
C13	0.5908 (6)	0.3095 (7)	0.4042 (5)	0.0835 (17)
H13A	0.6325	0.2653	0.4819	0.100*
H13B	0.6414	0.3830	0.3510	0.100*
C14	0.6302 (6)	0.1951 (5)	0.3306 (5)	0.0701 (13)
H14A	0.7453	0.1528	0.3059	0.084*
H14B	0.5862	0.1179	0.3862	0.084*
H2B	0.8210 (13)	0.423 (5)	0.029 (5)	0.080*
H2A	0.699 (4)	0.524 (4)	0.086 (4)	0.080*
H2	0.611 (5)	0.327 (4)	0.168 (4)	0.080*

	U11	U22	U33	U12	U13	U23
Zn1	0.0453 (3)	0.0381 (2)	0.0358 (2)	−0.01543 (19)	−0.00516 (18)	−0.01193 (18)
Br1	0.0684 (3)	0.0803 (3)	0.0459 (2)	−0.0337 (3)	−0.0178 (2)	−0.0131 (2)
Br2	0.0462 (3)	0.0559 (3)	0.0720 (3)	−0.0217 (2)	−0.0069 (2)	−0.0184 (2)
O1	0.0509 (16)	0.0409 (14)	0.0377 (14)	−0.0066 (12)	−0.0070 (12)	−0.0138 (11)
O2	0.0503 (17)	0.0479 (16)	0.0572 (18)	−0.0181 (14)	−0.0049 (14)	−0.0170 (13)
N1	0.0497 (19)	0.0346 (16)	0.0412 (17)	−0.0198 (14)	−0.0023 (14)	−0.0134 (13)
N2	0.0438 (19)	0.0411 (18)	0.0415 (17)	−0.0163 (15)	−0.0001 (14)	−0.0157 (14)
C1	0.041 (2)	0.041 (2)	0.0329 (18)	−0.0188 (17)	−0.0024 (15)	−0.0099 (15)
C2	0.033 (2)	0.044 (2)	0.0387 (19)	−0.0167 (16)	−0.0012 (15)	−0.0128 (16)
C3	0.046 (2)	0.044 (2)	0.049 (2)	−0.0169 (18)	−0.0028 (18)	−0.0200 (18)
C4	0.059 (3)	0.071 (3)	0.049 (2)	−0.030 (2)	0.001 (2)	−0.031 (2)
C5	0.071 (3)	0.081 (3)	0.034 (2)	−0.040 (3)	−0.002 (2)	−0.013 (2)
C6	0.057 (3)	0.054 (2)	0.042 (2)	−0.023 (2)	−0.0084 (19)	−0.0033 (18)
C7	0.039 (2)	0.0348 (19)	0.047 (2)	−0.0154 (16)	−0.0043 (17)	−0.0070 (16)
C8	0.064 (3)	0.043 (2)	0.059 (3)	−0.022 (2)	0.001 (2)	−0.0222 (19)
C9	0.061 (3)	0.063 (3)	0.076 (3)	−0.026 (2)	0.001 (2)	−0.037 (2)
C10	0.046 (3)	0.062 (3)	0.074 (3)	−0.018 (2)	−0.011 (2)	−0.022 (2)
C11	0.040 (3)	0.071 (3)	0.140 (5)	−0.011 (2)	0.002 (3)	−0.056 (4)
C12	0.083 (4)	0.141 (5)	0.084 (4)	−0.056 (4)	0.023 (3)	−0.073 (4)
C13	0.077 (4)	0.140 (5)	0.050 (3)	−0.045 (4)	−0.013 (3)	−0.030 (3)
C14	0.055 (3)	0.074 (3)	0.065 (3)	−0.011 (3)	−0.019 (2)	−0.002 (3)

Zn1—O1	1.936 (2)	C5—H5	0.9300
Zn1—N1	2.024 (3)	C6—H6	0.9300
Zn1—Br1	2.3417 (7)	C7—H7	0.9300
Zn1—Br2	2.3991 (7)	C8—C9	1.488 (6)
O1—C2	1.321 (4)	C8—H8A	0.9700
O2—H2B	0.86 (3)	C8—H8B	0.9700
O2—H2A	0.85 (4)	C9—H9A	0.9700
N1—C7	1.282 (5)	C9—H9B	0.9700
N1—C8	1.467 (4)	C10—C11	1.519 (6)
N2—C10	1.487 (5)	C10—H10A	0.9700
N2—C14	1.491 (5)	C10—H10B	0.9700
N2—C9	1.503 (5)	C11—C12	1.496 (8)
N2—H2	0.90 (4)	C11—H11A	0.9700
C1—C2	1.404 (5)	C11—H11B	0.9700
C1—C6	1.415 (5)	C12—C13	1.485 (7)
C1—C7	1.454 (5)	C12—H12A	0.9700
C2—C3	1.411 (5)	C12—H12B	0.9700
C3—C4	1.370 (6)	C13—C14	1.502 (7)
C3—H3	0.9300	C13—H13A	0.9700
C4—C5	1.389 (6)	C13—H13B	0.9700
C4—H4	0.9300	C14—H14A	0.9700
C5—C6	1.371 (6)	C14—H14B	0.9700
O1—Zn1—N1	93.91 (11)	C9—C8—H8A	109.7
O1—Zn1—Br1	116.12 (8)	N1—C8—H8B	109.7
N1—Zn1—Br1	113.04 (8)	C9—C8—H8B	109.7
O1—Zn1—Br2	109.78 (8)	H8A—C8—H8B	108.2
N1—Zn1—Br2	108.84 (9)	C8—C9—N2	112.2 (3)
Br1—Zn1—Br2	113.42 (2)	C8—C9—H9A	109.2
C2—O1—Zn1	121.6 (2)	N2—C9—H9A	109.2
H2B—O2—H2A	105 (2)	C8—C9—H9B	109.2
C7—N1—C8	117.3 (3)	N2—C9—H9B	109.2
C7—N1—Zn1	119.8 (2)	H9A—C9—H9B	107.9
C8—N1—Zn1	122.8 (2)	N2—C10—C11	110.8 (3)
C10—N2—C14	111.0 (3)	N2—C10—H10A	109.5
C10—N2—C9	108.7 (3)	C11—C10—H10A	109.5
C14—N2—C9	113.6 (3)	N2—C10—H10B	109.5
C10—N2—H2	108 (3)	C11—C10—H10B	109.5
C14—N2—H2	102 (3)	H10A—C10—H10B	108.1
C9—N2—H2	113 (3)	C12—C11—C10	111.6 (4)
C2—C1—C6	119.5 (3)	C12—C11—H11A	109.3
C2—C1—C7	125.2 (3)	C10—C11—H11A	109.3
C6—C1—C7	115.1 (3)	C12—C11—H11B	109.3
O1—C2—C1	123.9 (3)	C10—C11—H11B	109.3
O1—C2—C3	118.6 (3)	H11A—C11—H11B	108.0
C1—C2—C3	117.4 (3)	C13—C12—C11	110.0 (4)
C4—C3—C2	121.6 (4)	C13—C12—H12A	109.7
C4—C3—H3	119.2	C11—C12—H12A	109.7
C2—C3—H3	119.2	C13—C12—H12B	109.7
C3—C4—C5	121.2 (4)	C11—C12—H12B	109.7
C3—C4—H4	119.4	H12A—C12—H12B	108.2
C5—C4—H4	119.4	C12—C13—C14	110.9 (4)
C6—C5—C4	118.4 (4)	C12—C13—H13A	109.5
C6—C5—H5	120.8	C14—C13—H13A	109.5
C4—C5—H5	120.8	C12—C13—H13B	109.5
C5—C6—C1	121.8 (4)	C14—C13—H13B	109.5
C5—C6—H6	119.1	H13A—C13—H13B	108.0
C1—C6—H6	119.1	N2—C14—C13	111.4 (4)
N1—C7—C1	126.2 (3)	N2—C14—H14A	109.4
N1—C7—H7	116.9	C13—C14—H14A	109.4
C1—C7—H7	116.9	N2—C14—H14B	109.4
N1—C8—C9	109.9 (3)	C13—C14—H14B	109.4
N1—C8—H8A	109.7	H14A—C14—H14B	108.0

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.90 (4)	1.89 (4)	2.777 (4)	169 (4)
O2—H2A···Br2i	0.85 (4)	2.57 (4)	3.399 (3)	165 (4)
O2—H2B···O1ii	0.86 (3)	1.93 (4)	2.762 (4)	165 (5)

Zn1—O1	1.936 (2)
Zn1—N1	2.024 (3)
Zn1—Br1	2.3417 (7)
Zn1—Br2	2.3991 (7)

O1—Zn1—N1	93.91 (11)
O1—Zn1—Br1	116.12 (8)
N1—Zn1—Br1	113.04 (8)
O1—Zn1—Br2	109.78 (8)
N1—Zn1—Br2	108.84 (9)
Br1—Zn1—Br2	113.42 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.90 (4)	1.89 (4)	2.777 (4)	169 (4)
O2—H2A⋯Br2i	0.85 (4)	2.57 (4)	3.399 (3)	165 (4)
O2—H2B⋯O1ii	0.86 (3)	1.93 (4)	2.762 (4)	165 (5)

Symmetry codes: (i) ; (ii) .