Dibromido{(E)-2-eth-oxy-6-[3-(methyl-ammonio)propyl-iminometh-yl]phenol-ato}zinc(II).

The title complex, [ZnBr(2)(C(13)H(20)N(2)O(2))], is a mononuclear zinc(II) compound derived from the zwitterionic form of the Schiff base (E)-2-eth-oxy-6-((3-(methyl-amino)propyl-imino)meth-yl)phenol. The Zn(II) atom is four-coordinated by the imine N and phenolate O atoms of the Schiff base ligand, and by two bromide ions, in a tetra-hedral coordination geometry. Adjacent mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For background to the chemistry of the Schiff base complexes, see: Ali et al. (2008 ▶); Biswas et al. (2008 ▶); Chen et al. (2008 ▶); Darensbourg & Frantz (2007 ▶); Habibi et al. (2007 ▶); Kawamoto et al. (2008 ▶); Lipscomb & Sträter (1996 ▶); Tomat et al. (2007 ▶); Wu et al. (2008 ▶); Yuan et al. (2007 ▶). For related structures, see: Qiu (2006 ▶); Wei et al. (2007 ▶); Zhu et al. (2007 ▶).

Experimental

Crystal data

[ZnBr2(C13H20N2O2)]

M = 461.50

Monoclinic,

a = 17.884 (3) Å

b = 14.374 (2) Å

c = 14.992 (2) Å

β = 114.482 (3)°

V = 3507.4 (9) Å3

Z = 8

Mo Kα radiation

μ = 5.96 mm−1

T = 298 (2) K

0.23 × 0.21 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.341, T max = 0.367 (expected range = 0.265–0.286)

14138 measured reflections

3787 independent reflections

1974 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.222

S = 1.00

3787 reflections

183 parameters

H-atom parameters constrained

Δρmax = 1.12 e Å−3

Δρmin = −0.90 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536808023672/sj2525sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023672/sj2525Isup2.hkl

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

[ZnBr2(C13H20N2O2)]	F000 = 1824
Mr = 461.50	Dx = 1.748 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1842 reflections
a = 17.884 (3) Å	θ = 2.4–24.1º
b = 14.374 (2) Å	µ = 5.96 mm−1
c = 14.992 (2) Å	T = 298 (2) K
β = 114.482 (3)º	Block, colorless
V = 3507.4 (9) Å3	0.23 × 0.21 × 0.21 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	3787 independent reflections
Radiation source: fine-focus sealed tube	1974 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.068
T = 298(2) K	θmax = 27.0º
ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −22→22
Tmin = 0.341, Tmax = 0.368	k = −18→18
14138 measured reflections	l = −18→18

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)] = 0.067	H-atom parameters constrained
wR(F2) = 0.222	w = 1/[σ2(Fo2) + (0.1251P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
3787 reflections	Δρmax = 1.12 e Å−3
183 parameters	Δρmin = −0.90 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.27393 (5)	0.33839 (6)	0.31911 (7)	0.0412 (3)
Br1	0.41500 (7)	0.37049 (9)	0.38443 (10)	0.0911 (5)
Br2	0.22492 (8)	0.35250 (9)	0.14417 (9)	0.0842 (4)
O1	0.2106 (3)	0.4129 (3)	0.3728 (4)	0.0457 (13)
O2	0.1034 (3)	0.5348 (4)	0.3750 (4)	0.0524 (15)
N1	0.2463 (4)	0.2150 (4)	0.3615 (5)	0.0435 (15)
N2	0.2234 (4)	0.0849 (4)	0.0895 (5)	0.0506 (17)
H2A	0.2508	0.1333	0.0793	0.061*
H2B	0.2536	0.0335	0.0945	0.061*
C1	0.1272 (5)	0.2825 (6)	0.3792 (6)	0.049 (2)
C2	0.1426 (4)	0.3790 (5)	0.3754 (5)	0.0394 (17)
C3	0.0835 (5)	0.4402 (6)	0.3797 (5)	0.047 (2)
C4	0.0121 (5)	0.4091 (8)	0.3825 (6)	0.065 (3)
H4	−0.0272	0.4517	0.3819	0.078*
C5	−0.0022 (6)	0.3135 (8)	0.3860 (7)	0.074 (3)
H5	−0.0509	0.2930	0.3879	0.089*
C6	0.0554 (6)	0.2503 (8)	0.3869 (7)	0.068 (3)
H6	0.0473	0.1870	0.3924	0.082*
C7	0.1826 (6)	0.2104 (5)	0.3813 (6)	0.055 (2)
H7	0.1713	0.1520	0.3995	0.066*
C8	0.2915 (6)	0.1308 (6)	0.3638 (7)	0.057 (2)
H8A	0.2641	0.0783	0.3781	0.069*
H8B	0.3462	0.1354	0.4162	0.069*
C9	0.2982 (5)	0.1139 (6)	0.2700 (6)	0.055 (2)
H9A	0.3320	0.0593	0.2767	0.067*
H9B	0.3253	0.1665	0.2557	0.067*
C10	0.2170 (5)	0.0998 (6)	0.1873 (7)	0.057 (2)
H10A	0.1828	0.1536	0.1818	0.068*
H10B	0.1906	0.0461	0.2009	0.068*
C11	0.1458 (5)	0.0750 (7)	0.0041 (7)	0.065 (3)
H11A	0.1211	0.0166	0.0073	0.097*
H11B	0.1554	0.0771	−0.0543	0.097*
H11C	0.1097	0.1249	0.0029	0.097*
C12	0.0459 (6)	0.6012 (7)	0.3834 (7)	0.065 (3)
H12A	0.0413	0.5924	0.4450	0.079*
H12B	−0.0079	0.5922	0.3304	0.079*
C13	0.0754 (6)	0.6948 (8)	0.3788 (8)	0.084 (4)
H13A	0.1295	0.7025	0.4299	0.127*
H13B	0.0389	0.7395	0.3872	0.127*
H13C	0.0771	0.7041	0.3163	0.127*

	U11	U22	U33	U12	U13	U23
Zn1	0.0429 (5)	0.0361 (5)	0.0501 (6)	0.0014 (4)	0.0248 (4)	−0.0029 (4)
Br1	0.0580 (7)	0.0846 (8)	0.1261 (11)	0.0068 (5)	0.0335 (7)	−0.0125 (7)
Br2	0.0864 (8)	0.0953 (9)	0.0692 (8)	−0.0150 (6)	0.0305 (6)	0.0043 (6)
O1	0.042 (3)	0.036 (3)	0.071 (4)	0.001 (2)	0.034 (3)	−0.006 (3)
O2	0.046 (3)	0.061 (4)	0.051 (4)	0.019 (3)	0.021 (3)	−0.007 (3)
N1	0.049 (4)	0.038 (4)	0.042 (4)	0.000 (3)	0.017 (3)	−0.001 (3)
N2	0.050 (4)	0.035 (4)	0.061 (5)	0.005 (3)	0.018 (4)	0.006 (3)
C1	0.046 (5)	0.064 (6)	0.041 (5)	−0.017 (4)	0.022 (4)	−0.006 (4)
C2	0.040 (4)	0.046 (4)	0.030 (4)	0.000 (3)	0.012 (3)	−0.002 (3)
C3	0.044 (5)	0.067 (6)	0.032 (5)	0.012 (4)	0.017 (4)	0.001 (4)
C4	0.039 (5)	0.113 (9)	0.050 (6)	0.013 (5)	0.026 (4)	0.012 (5)
C5	0.057 (6)	0.103 (9)	0.069 (7)	−0.030 (6)	0.033 (5)	−0.011 (6)
C6	0.066 (6)	0.085 (7)	0.066 (7)	−0.013 (6)	0.039 (6)	−0.002 (6)
C7	0.084 (7)	0.029 (4)	0.053 (6)	−0.005 (4)	0.030 (5)	−0.006 (4)
C8	0.078 (6)	0.030 (4)	0.057 (6)	0.009 (4)	0.021 (5)	0.008 (4)
C9	0.051 (5)	0.042 (5)	0.061 (6)	0.002 (4)	0.012 (4)	−0.019 (4)
C10	0.042 (5)	0.043 (5)	0.078 (7)	−0.001 (4)	0.018 (5)	−0.014 (5)
C11	0.059 (6)	0.065 (6)	0.064 (6)	−0.005 (5)	0.019 (5)	0.010 (5)
C12	0.070 (6)	0.078 (7)	0.055 (6)	0.038 (5)	0.032 (5)	0.006 (5)
C13	0.084 (7)	0.074 (7)	0.071 (7)	0.038 (6)	0.007 (6)	−0.024 (6)

Zn1—O1	1.958 (5)	C5—H5	0.9300
Zn1—N1	2.014 (6)	C6—H6	0.9300
Zn1—Br1	2.3429 (16)	C7—H7	0.9300
Zn1—Br2	2.4046 (18)	C8—C9	1.480 (12)
O1—C2	1.325 (8)	C8—H8A	0.9700
O2—C3	1.414 (11)	C8—H8B	0.9700
O2—C12	1.446 (9)	C9—C10	1.481 (11)
N1—C7	1.293 (11)	C9—H9A	0.9700
N1—C8	1.447 (10)	C9—H9B	0.9700
N2—C11	1.453 (10)	C10—H10A	0.9700
N2—C10	1.532 (11)	C10—H10B	0.9700
N2—H2A	0.9000	C11—H11A	0.9600
N2—H2B	0.9000	C11—H11B	0.9600
C1—C6	1.414 (12)	C11—H11C	0.9600
C1—C2	1.420 (11)	C12—C13	1.456 (15)
C1—C7	1.423 (12)	C12—H12A	0.9700
C2—C3	1.396 (11)	C12—H12B	0.9700
C3—C4	1.370 (12)	C13—H13A	0.9600
C4—C5	1.403 (15)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
C5—C6	1.369 (14)
O1—Zn1—N1	95.3 (2)	C1—C7—H7	115.5
O1—Zn1—Br1	115.26 (16)	N1—C8—C9	112.2 (7)
N1—Zn1—Br1	113.83 (19)	N1—C8—H8A	109.2
O1—Zn1—Br2	113.02 (17)	C9—C8—H8A	109.2
N1—Zn1—Br2	113.09 (19)	N1—C8—H8B	109.2
Br1—Zn1—Br2	106.38 (6)	C9—C8—H8B	109.2
C2—O1—Zn1	120.3 (4)	H8A—C8—H8B	107.9
C3—O2—C12	115.4 (7)	C8—C9—C10	112.4 (8)
C7—N1—C8	119.3 (7)	C8—C9—H9A	109.1
C7—N1—Zn1	118.1 (5)	C10—C9—H9A	109.1
C8—N1—Zn1	122.5 (6)	C8—C9—H9B	109.1
C11—N2—C10	115.7 (7)	C10—C9—H9B	109.1
C11—N2—H2A	108.4	H9A—C9—H9B	107.9
C10—N2—H2A	108.4	C9—C10—N2	112.7 (7)
C11—N2—H2B	108.4	C9—C10—H10A	109.1
C10—N2—H2B	108.4	N2—C10—H10A	109.1
H2A—N2—H2B	107.4	C9—C10—H10B	109.1
C6—C1—C2	121.3 (8)	N2—C10—H10B	109.1
C6—C1—C7	114.0 (8)	H10A—C10—H10B	107.8
C2—C1—C7	124.6 (7)	N2—C11—H11A	109.5
O1—C2—C3	119.4 (7)	N2—C11—H11B	109.5
O1—C2—C1	123.7 (7)	H11A—C11—H11B	109.5
C3—C2—C1	116.8 (7)	N2—C11—H11C	109.5
C4—C3—C2	121.9 (9)	H11A—C11—H11C	109.5
C4—C3—O2	124.8 (8)	H11B—C11—H11C	109.5
C2—C3—O2	113.1 (7)	O2—C12—C13	108.8 (8)
C3—C4—C5	120.5 (9)	O2—C12—H12A	109.9
C3—C4—H4	119.8	C13—C12—H12A	109.9
C5—C4—H4	119.8	O2—C12—H12B	109.9
C6—C5—C4	120.1 (9)	C13—C12—H12B	109.9
C6—C5—H5	119.9	H12A—C12—H12B	108.3
C4—C5—H5	119.9	C12—C13—H13A	109.5
C5—C6—C1	119.2 (9)	C12—C13—H13B	109.5
C5—C6—H6	120.4	H13A—C13—H13B	109.5
C1—C6—H6	120.4	C12—C13—H13C	109.5
N1—C7—C1	129.0 (8)	H13A—C13—H13C	109.5
N1—C7—H7	115.5	H13B—C13—H13C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1i	0.90	1.84	2.697 (8)	158
N2—H2B···O2i	0.90	2.40	3.005 (8)	124

Zn1—O1	1.958 (5)
Zn1—N1	2.014 (6)
Zn1—Br1	2.3429 (16)
Zn1—Br2	2.4046 (18)

O1—Zn1—N1	95.3 (2)
O1—Zn1—Br1	115.26 (16)
N1—Zn1—Br1	113.83 (19)
O1—Zn1—Br2	113.02 (17)
N1—Zn1—Br2	113.09 (19)
Br1—Zn1—Br2	106.38 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1i	0.90	1.84	2.697 (8)	158
N2—H2B⋯O2i	0.90	2.40	3.005 (8)	124

Symmetry code: (i) .