{(E)-2-Bromo-4-chloro-6-[3-(dimethyl-ammonio)propyl-imino-meth-yl]-phenol-ato}-dichloridozinc(II).

The title compound, [ZnCl(2)(C(12)H(16)BrClN(2)O)], is a mononuclear zinc(II) complex. The Zn(II) atom is four-coordinate in a tetra-hedral geometry, binding to the phenolate O and imine N atoms of the zwitterionic Schiff base ligand and to two Cl(-) ions. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯Cl hydrogen bonds to form chains running along the a axis.

Related literature

For related structures, see: Ali et al. (2008 ▶); Wang (2007 ▶); You (2005 ▶). For our recent investigations of metal complex systems, see: Ye & You (2007a ▶,b ▶,c ▶).

Experimental

Crystal data

[ZnCl2(C12H16BrClN2O)]

M = 455.90

Monoclinic,

a = 7.522 (4) Å

b = 26.808 (15) Å

c = 8.354 (4) Å

β = 90.921 (9)°

V = 1684.3 (16) Å3

Z = 4

Mo Kα radiation

μ = 4.30 mm−1

T = 298 (2) K

0.32 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.261, T max = 0.275

9470 measured reflections

3633 independent reflections

2283 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.126

S = 1.04

3633 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.58 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016255/sj2511sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016255/sj2511Isup2.hkl

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

[ZnCl2(C12H16BrClN2O)]	F000 = 904
Mr = 455.90	Dx = 1.798 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1372 reflections
a = 7.522 (4) Å	θ = 2.3–25.3º
b = 26.808 (15) Å	µ = 4.30 mm−1
c = 8.354 (4) Å	T = 298 (2) K
β = 90.921 (9)º	Block, colorless
V = 1684.3 (16) Å3	0.32 × 0.30 × 0.30 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3633 independent reflections
Radiation source: fine-focus sealed tube	2283 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
T = 298(2) K	θmax = 27.0º
ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.261, Tmax = 0.275	k = −32→34
9470 measured reflections	l = −10→7

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) = 0.126	w = 1/[σ2(Fo2) + (0.0506P)2 + 2.1641P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3633 reflections	Δρmax = 0.58 e Å−3
186 parameters	Δρmin = −0.36 e Å−3
1 restraint	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	0.25129 (8)	0.59843 (2)	0.53367 (8)	0.0531 (2)
Br1	−0.09048 (7)	0.73965 (3)	0.73104 (8)	0.0691 (2)
Cl1	0.4472 (2)	0.86120 (6)	0.5360 (2)	0.0868 (6)
Cl2	0.1025 (2)	0.56893 (7)	0.32087 (19)	0.0748 (5)
Cl3	0.2609 (2)	0.54111 (6)	0.7302 (2)	0.0718 (4)
O1	0.1550 (5)	0.66062 (14)	0.6102 (5)	0.0592 (10)
N1	0.4876 (5)	0.62653 (18)	0.4750 (5)	0.0485 (10)
N2	0.8671 (7)	0.5717 (2)	0.8271 (6)	0.0708 (15)
C1	0.3975 (6)	0.7126 (2)	0.5273 (6)	0.0465 (12)
C2	0.2268 (6)	0.7039 (2)	0.5936 (6)	0.0464 (12)
C3	0.1364 (6)	0.7472 (2)	0.6440 (6)	0.0499 (13)
C4	0.2038 (7)	0.7947 (2)	0.6301 (6)	0.0554 (14)
H4	0.1408	0.8221	0.6675	0.066*
C5	0.3661 (7)	0.8009 (2)	0.5599 (7)	0.0561 (14)
C6	0.4609 (7)	0.7608 (2)	0.5106 (7)	0.0545 (14)
H6	0.5712	0.7658	0.4645	0.065*
C7	0.5140 (6)	0.6730 (2)	0.4739 (6)	0.0501 (13)
H7	0.6226	0.6832	0.4335	0.060*
C8	0.6332 (7)	0.5932 (2)	0.4223 (7)	0.0566 (14)
H8A	0.7281	0.6131	0.3776	0.068*
H8B	0.5886	0.5709	0.3394	0.068*
C9	0.7047 (7)	0.5631 (2)	0.5607 (7)	0.0562 (14)
H9A	0.8007	0.5420	0.5245	0.067*
H9B	0.6115	0.5418	0.6012	0.067*
C10	0.7721 (7)	0.5967 (2)	0.6924 (6)	0.0557 (14)
H10A	0.8515	0.6211	0.6462	0.067*
H10B	0.6717	0.6147	0.7353	0.067*
C11	0.9452 (10)	0.6088 (3)	0.9358 (8)	0.094 (2)
H11A	1.0131	0.6323	0.8755	0.140*
H11B	1.0216	0.5924	1.0125	0.140*
H11C	0.8522	0.6259	0.9906	0.140*
C12	0.7535 (10)	0.5353 (3)	0.9111 (9)	0.092 (2)
H12A	0.8145	0.5236	1.0058	0.137*
H12B	0.7283	0.5075	0.8417	0.137*
H12C	0.6442	0.5510	0.9404	0.137*
H2	0.957 (6)	0.5538 (19)	0.785 (7)	0.080*

	U11	U22	U33	U12	U13	U23
Zn1	0.0387 (3)	0.0640 (4)	0.0565 (4)	0.0016 (3)	0.0037 (3)	0.0026 (3)
Br1	0.0423 (3)	0.0841 (5)	0.0814 (5)	0.0067 (3)	0.0171 (3)	−0.0044 (4)
Cl1	0.0821 (12)	0.0638 (10)	0.1152 (15)	−0.0146 (9)	0.0261 (10)	0.0035 (10)
Cl2	0.0598 (9)	0.1019 (13)	0.0625 (10)	−0.0042 (9)	−0.0082 (7)	−0.0015 (9)
Cl3	0.0628 (9)	0.0818 (11)	0.0713 (10)	0.0011 (8)	0.0118 (7)	0.0115 (9)
O1	0.045 (2)	0.056 (2)	0.077 (3)	0.0007 (18)	0.0174 (18)	0.005 (2)
N1	0.033 (2)	0.062 (3)	0.051 (3)	0.009 (2)	0.0019 (18)	0.003 (2)
N2	0.057 (3)	0.095 (4)	0.061 (3)	0.035 (3)	0.007 (2)	0.016 (3)
C1	0.033 (2)	0.064 (3)	0.042 (3)	0.002 (2)	−0.002 (2)	0.001 (3)
C2	0.034 (2)	0.062 (4)	0.043 (3)	0.006 (2)	−0.002 (2)	0.005 (3)
C3	0.036 (3)	0.067 (4)	0.046 (3)	0.006 (2)	0.000 (2)	0.006 (3)
C4	0.056 (3)	0.058 (4)	0.052 (3)	0.009 (3)	−0.004 (3)	−0.001 (3)
C5	0.050 (3)	0.060 (4)	0.058 (4)	−0.002 (3)	0.001 (3)	0.004 (3)
C6	0.039 (3)	0.070 (4)	0.055 (3)	−0.003 (3)	−0.002 (2)	0.004 (3)
C7	0.032 (2)	0.077 (4)	0.041 (3)	0.008 (3)	0.006 (2)	0.008 (3)
C8	0.040 (3)	0.072 (4)	0.058 (4)	0.014 (3)	0.006 (2)	−0.004 (3)
C9	0.040 (3)	0.061 (3)	0.068 (4)	0.014 (3)	0.011 (3)	0.000 (3)
C10	0.041 (3)	0.072 (4)	0.054 (3)	0.011 (3)	0.002 (2)	0.012 (3)
C11	0.081 (5)	0.155 (7)	0.044 (4)	0.008 (5)	−0.010 (3)	−0.003 (4)
C12	0.109 (6)	0.084 (5)	0.083 (5)	0.028 (4)	0.034 (4)	0.031 (4)

Zn1—O1	1.931 (4)	C4—H4	0.9300
Zn1—N1	1.999 (4)	C5—C6	1.359 (8)
Zn1—Cl2	2.2303 (19)	C6—H6	0.9300
Zn1—Cl3	2.2489 (19)	C7—H7	0.9300
Br1—C3	1.877 (5)	C8—C9	1.502 (8)
Cl1—C5	1.740 (6)	C8—H8A	0.9700
O1—C2	1.288 (6)	C8—H8B	0.9700
N1—C7	1.261 (7)	C9—C10	1.504 (8)
N1—C8	1.485 (6)	C9—H9A	0.9700
N2—C11	1.464 (9)	C9—H9B	0.9700
N2—C12	1.482 (8)	C10—H10A	0.9700
N2—C10	1.483 (7)	C10—H10B	0.9700
N2—H2	0.91 (5)	C11—H11A	0.9600
C1—C6	1.385 (8)	C11—H11B	0.9600
C1—C2	1.425 (7)	C11—H11C	0.9600
C1—C7	1.451 (7)	C12—H12A	0.9600
C2—C3	1.413 (7)	C12—H12B	0.9600
C3—C4	1.375 (8)	C12—H12C	0.9600
C4—C5	1.372 (8)
O1—Zn1—N1	95.48 (17)	N1—C7—C1	128.6 (5)
O1—Zn1—Cl2	112.60 (13)	N1—C7—H7	115.7
N1—Zn1—Cl2	112.04 (14)	C1—C7—H7	115.7
O1—Zn1—Cl3	110.85 (13)	N1—C8—C9	110.6 (4)
N1—Zn1—Cl3	114.71 (13)	N1—C8—H8A	109.5
Cl2—Zn1—Cl3	110.45 (8)	C9—C8—H8A	109.5
C2—O1—Zn1	125.6 (3)	N1—C8—H8B	109.5
C7—N1—C8	118.4 (4)	C9—C8—H8B	109.5
C7—N1—Zn1	121.0 (3)	H8A—C8—H8B	108.1
C8—N1—Zn1	120.6 (4)	C8—C9—C10	110.7 (5)
C11—N2—C12	112.5 (6)	C8—C9—H9A	109.5
C11—N2—C10	110.3 (5)	C10—C9—H9A	109.5
C12—N2—C10	112.5 (5)	C8—C9—H9B	109.5
C11—N2—H2	108 (4)	C10—C9—H9B	109.5
C12—N2—H2	106 (4)	H9A—C9—H9B	108.1
C10—N2—H2	107 (4)	N2—C10—C9	115.9 (5)
C6—C1—C2	120.3 (5)	N2—C10—H10A	108.3
C6—C1—C7	116.1 (5)	C9—C10—H10A	108.3
C2—C1—C7	123.6 (5)	N2—C10—H10B	108.3
O1—C2—C3	120.3 (4)	C9—C10—H10B	108.3
O1—C2—C1	124.7 (5)	H10A—C10—H10B	107.4
C3—C2—C1	115.0 (5)	N2—C11—H11A	109.5
C4—C3—C2	123.7 (5)	N2—C11—H11B	109.5
C4—C3—Br1	118.2 (4)	H11A—C11—H11B	109.5
C2—C3—Br1	118.1 (4)	N2—C11—H11C	109.5
C5—C4—C3	118.7 (5)	H11A—C11—H11C	109.5
C5—C4—H4	120.7	H11B—C11—H11C	109.5
C3—C4—H4	120.7	N2—C12—H12A	109.5
C6—C5—C4	120.5 (5)	N2—C12—H12B	109.5
C6—C5—Cl1	121.0 (4)	H12A—C12—H12B	109.5
C4—C5—Cl1	118.5 (5)	N2—C12—H12C	109.5
C5—C6—C1	121.7 (5)	H12A—C12—H12C	109.5
C5—C6—H6	119.2	H12B—C12—H12C	109.5
C1—C6—H6	119.2

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Cl3i	0.91 (5)	2.37 (3)	3.190 (5)	152 (5)

Zn1—O1	1.931 (4)
Zn1—N1	1.999 (4)
Zn1—Cl2	2.2303 (19)
Zn1—Cl3	2.2489 (19)

O1—Zn1—N1	95.48 (17)
O1—Zn1—Cl2	112.60 (13)
N1—Zn1—Cl2	112.04 (14)
O1—Zn1—Cl3	110.85 (13)
N1—Zn1—Cl3	114.71 (13)
Cl2—Zn1—Cl3	110.45 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Cl3i	0.91 (5)	2.37 (3)	3.190 (5)	152 (5)

Symmetry code: (i) .