(Acetato-κO)(2-bromo-6-{[3-(dimethyl-aza-nium-yl)propyl-imino-κN]meth-yl}phenolato-κO)(thio-cyanato-κN)zinc.

In the title compound, [Zn(CH(3)COO)(NCS)(C(12)H(17)BrN(2)O)], the Zn(II) atom is four-coordinated in a distorted tetra-hedral geometry, binding to a phenolate O and an imine N atom of the Schiff base ligand, the O atom of an acetate ligand and one thio-cyanate N atom. In the crystal, mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For a zinc Schiff base complex reported previously by the author, see: Han (2009 ▶). For related zinc complexes, see: Ali et al. (2008 ▶); You (2005 ▶); Zhu & Yang (2008 ▶).

Experimental

Crystal data

[Zn(C2H3O2)(NCS)(C12H17BrN2O)]

M = 467.68

Triclinic,

a = 9.3091 (6) Å

b = 10.2687 (6) Å

c = 11.8353 (7) Å

α = 66.299 (2)°

β = 79.891 (2)°

γ = 88.122 (2)°

V = 1018.96 (11) Å3

Z = 2

Mo Kα radiation

μ = 3.28 mm−1

T = 298 K

0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.605, T max = 0.639

9684 measured reflections

3720 independent reflections

3021 reflections with I > 2σ(I)

R int = 0.129

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.201

S = 1.07

3720 reflections

220 parameters

H-atom parameters constrained

Δρmax = 1.32 e Å−3

Δρmin = −0.61 e Å−3

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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812017564/su2407sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017564/su2407Isup2.hkl

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

[Zn(C2H3O2)(NCS)(C12H17BrN2O)]	Z = 2
Mr = 467.68	F(000) = 472
Triclinic, P1	Dx = 1.524 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3091 (6) Å	Cell parameters from 5991 reflections
b = 10.2687 (6) Å	θ = 2.2–27.9°
c = 11.8353 (7) Å	µ = 3.28 mm−1
α = 66.299 (2)°	T = 298 K
β = 79.891 (2)°	Block, colourless
γ = 88.122 (2)°	0.17 × 0.15 × 0.15 mm
V = 1018.96 (11) Å3

Bruker SMART CCD area-detector diffractometer	3720 independent reflections
Radiation source: fine-focus sealed tube	3021 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.129
ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.605, Tmax = 0.639	k = −12→12
9684 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0811P)2 + 2.5468P] where P = (Fo2 + 2Fc2)/3
3720 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 1.32 e Å−3
0 restraints	Δρmin = −0.61 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.71920 (7)	0.16314 (7)	0.17582 (7)	0.0445 (3)
Br1	0.86805 (11)	0.41595 (10)	0.41002 (10)	0.0872 (4)
N1	0.5145 (5)	0.0900 (5)	0.2551 (5)	0.0429 (11)
N2	0.2396 (5)	0.2871 (5)	−0.0322 (5)	0.0436 (11)
H2	0.2172	0.2258	−0.0653	0.052*
N3	0.7308 (6)	0.2974 (7)	0.0016 (6)	0.0642 (15)
O1	0.7416 (5)	0.2599 (5)	0.2823 (5)	0.0599 (12)
O2	0.8893 (5)	0.0442 (5)	0.1972 (5)	0.0598 (12)
O3	0.7888 (5)	−0.0922 (5)	0.1276 (5)	0.0565 (11)
S1	0.7396 (3)	0.5055 (2)	−0.2352 (2)	0.0807 (6)
C1	0.5007 (7)	0.1983 (6)	0.4068 (5)	0.0478 (14)
C2	0.6446 (7)	0.2621 (6)	0.3737 (6)	0.0475 (14)
C3	0.6772 (9)	0.3331 (6)	0.4473 (7)	0.0589 (17)
C4	0.5794 (11)	0.3442 (7)	0.5422 (7)	0.070 (2)
H4	0.6069	0.3901	0.5891	0.084*
C5	0.4342 (11)	0.2853 (8)	0.5701 (7)	0.075 (2)
H5	0.3646	0.2963	0.6320	0.090*
C6	0.4007 (9)	0.2134 (7)	0.5044 (6)	0.0640 (19)
H6	0.3073	0.1718	0.5243	0.077*
C7	0.4463 (7)	0.1182 (6)	0.3462 (6)	0.0473 (14)
H7	0.3503	0.0826	0.3767	0.057*
C8	0.4325 (7)	0.0049 (6)	0.2105 (6)	0.0486 (14)
H8A	0.3428	−0.0341	0.2699	0.058*
H8B	0.4903	−0.0740	0.2065	0.058*
C9	0.3960 (6)	0.0940 (6)	0.0817 (6)	0.0430 (13)
H9A	0.4839	0.1438	0.0248	0.052*
H9B	0.3587	0.0321	0.0485	0.052*
C10	0.2827 (6)	0.2011 (7)	0.0899 (6)	0.0468 (14)
H10A	0.1967	0.1508	0.1495	0.056*
H10B	0.3217	0.2641	0.1210	0.056*
C11	0.3592 (8)	0.3865 (8)	−0.1235 (8)	0.0659 (19)
H11A	0.3239	0.4437	−0.1991	0.099*
H11B	0.4392	0.3329	−0.1423	0.099*
H11C	0.3916	0.4470	−0.0879	0.099*
C12	0.1071 (7)	0.3664 (8)	−0.0167 (9)	0.074 (2)
H12A	0.0287	0.3006	0.0379	0.110*
H12B	0.0797	0.4187	−0.0969	0.110*
H12C	0.1269	0.4314	0.0192	0.110*
C13	0.7343 (6)	0.3843 (7)	−0.0990 (6)	0.0471 (14)
C14	0.8872 (6)	−0.0647 (6)	0.1725 (6)	0.0418 (13)
C15	1.0122 (8)	−0.1603 (8)	0.2014 (8)	0.068 (2)
H15A	0.9755	−0.2559	0.2535	0.102*
H15B	1.0720	−0.1286	0.2445	0.102*
H15C	1.0694	−0.1579	0.1247	0.102*

	U11	U22	U33	U12	U13	U23
Zn1	0.0424 (4)	0.0461 (4)	0.0530 (5)	0.0063 (3)	−0.0081 (3)	−0.0288 (3)
Br1	0.1033 (7)	0.0773 (6)	0.1037 (7)	−0.0066 (5)	−0.0388 (6)	−0.0506 (5)
N1	0.041 (2)	0.038 (2)	0.050 (3)	0.0034 (19)	−0.012 (2)	−0.017 (2)
N2	0.036 (2)	0.036 (2)	0.073 (3)	0.0091 (18)	−0.018 (2)	−0.034 (2)
N3	0.047 (3)	0.075 (4)	0.072 (4)	0.007 (3)	−0.010 (3)	−0.031 (3)
O1	0.056 (2)	0.069 (3)	0.072 (3)	−0.001 (2)	−0.008 (2)	−0.047 (3)
O2	0.053 (2)	0.057 (3)	0.095 (4)	0.016 (2)	−0.027 (2)	−0.052 (3)
O3	0.052 (2)	0.055 (2)	0.082 (3)	0.0154 (19)	−0.024 (2)	−0.044 (2)
S1	0.0938 (15)	0.0725 (13)	0.0613 (12)	−0.0063 (11)	−0.0086 (11)	−0.0134 (10)
C1	0.067 (4)	0.038 (3)	0.039 (3)	0.013 (3)	−0.012 (3)	−0.017 (2)
C2	0.062 (4)	0.039 (3)	0.049 (3)	0.013 (3)	−0.014 (3)	−0.024 (3)
C3	0.088 (5)	0.037 (3)	0.057 (4)	0.013 (3)	−0.023 (4)	−0.020 (3)
C4	0.127 (7)	0.044 (3)	0.049 (4)	0.018 (4)	−0.021 (4)	−0.027 (3)
C5	0.112 (7)	0.058 (4)	0.051 (4)	0.016 (4)	0.001 (4)	−0.025 (3)
C6	0.084 (5)	0.047 (3)	0.051 (4)	0.011 (3)	0.001 (3)	−0.015 (3)
C7	0.047 (3)	0.040 (3)	0.048 (3)	0.002 (2)	−0.004 (3)	−0.012 (3)
C8	0.046 (3)	0.040 (3)	0.062 (4)	0.003 (2)	−0.011 (3)	−0.022 (3)
C9	0.046 (3)	0.041 (3)	0.057 (3)	0.012 (2)	−0.020 (3)	−0.032 (3)
C10	0.042 (3)	0.051 (3)	0.061 (4)	0.012 (2)	−0.010 (3)	−0.035 (3)
C11	0.061 (4)	0.051 (4)	0.079 (5)	−0.003 (3)	−0.008 (4)	−0.021 (4)
C12	0.048 (3)	0.063 (4)	0.130 (7)	0.027 (3)	−0.028 (4)	−0.057 (5)
C13	0.038 (3)	0.053 (3)	0.055 (4)	0.002 (2)	−0.005 (3)	−0.027 (3)
C14	0.040 (3)	0.040 (3)	0.052 (3)	0.010 (2)	−0.007 (2)	−0.026 (3)
C15	0.058 (4)	0.059 (4)	0.104 (6)	0.023 (3)	−0.031 (4)	−0.045 (4)

Zn1—O1	1.931 (4)	C5—C6	1.345 (11)
Zn1—N3	1.952 (7)	C5—H5	0.9300
Zn1—O2	1.957 (4)	C6—H6	0.9300
Zn1—N1	1.994 (5)	C7—H7	0.9300
Br1—C3	1.897 (8)	C8—C9	1.523 (9)
N1—C7	1.284 (8)	C8—H8A	0.9700
N1—C8	1.476 (8)	C8—H8B	0.9700
N2—C10	1.477 (8)	C9—C10	1.518 (7)
N2—C12	1.482 (7)	C9—H9A	0.9700
N2—C11	1.488 (8)	C9—H9B	0.9700
N2—H2	0.9100	C10—H10A	0.9700
N3—C13	1.161 (9)	C10—H10B	0.9700
O1—C2	1.289 (7)	C11—H11A	0.9600
O2—C14	1.265 (7)	C11—H11B	0.9600
O3—C14	1.229 (7)	C11—H11C	0.9600
S1—C13	1.586 (7)	C12—H12A	0.9600
C1—C6	1.407 (9)	C12—H12B	0.9600
C1—C2	1.430 (9)	C12—H12C	0.9600
C1—C7	1.442 (9)	C14—C15	1.493 (8)
C2—C3	1.414 (9)	C15—H15A	0.9600
C3—C4	1.356 (11)	C15—H15B	0.9600
C4—C5	1.428 (13)	C15—H15C	0.9600
C4—H4	0.9300
O1—Zn1—N3	111.3 (2)	N1—C8—H8A	109.3
O1—Zn1—O2	100.4 (2)	C9—C8—H8A	109.3
N3—Zn1—O2	111.2 (2)	N1—C8—H8B	109.3
O1—Zn1—N1	96.3 (2)	C9—C8—H8B	109.3
N3—Zn1—N1	111.3 (2)	H8A—C8—H8B	108.0
O2—Zn1—N1	124.1 (2)	C10—C9—C8	110.5 (5)
C7—N1—C8	116.7 (5)	C10—C9—H9A	109.5
C7—N1—Zn1	121.0 (4)	C8—C9—H9A	109.5
C8—N1—Zn1	122.2 (4)	C10—C9—H9B	109.5
C10—N2—C12	111.3 (5)	C8—C9—H9B	109.5
C10—N2—C11	112.8 (5)	H9A—C9—H9B	108.1
C12—N2—C11	110.2 (5)	N2—C10—C9	112.7 (5)
C10—N2—H2	107.4	N2—C10—H10A	109.1
C12—N2—H2	107.4	C9—C10—H10A	109.1
C11—N2—H2	107.4	N2—C10—H10B	109.1
C13—N3—Zn1	175.3 (6)	C9—C10—H10B	109.1
C2—O1—Zn1	125.7 (4)	H10A—C10—H10B	107.8
C14—O2—Zn1	117.7 (4)	N2—C11—H11A	109.5
C6—C1—C2	119.7 (6)	N2—C11—H11B	109.5
C6—C1—C7	115.5 (6)	H11A—C11—H11B	109.5
C2—C1—C7	124.8 (5)	N2—C11—H11C	109.5
O1—C2—C3	119.9 (6)	H11A—C11—H11C	109.5
O1—C2—C1	124.3 (5)	H11B—C11—H11C	109.5
C3—C2—C1	115.8 (6)	N2—C12—H12A	109.5
C4—C3—C2	123.3 (7)	N2—C12—H12B	109.5
C4—C3—Br1	119.1 (6)	H12A—C12—H12B	109.5
C2—C3—Br1	117.6 (5)	N2—C12—H12C	109.5
C3—C4—C5	120.0 (7)	H12A—C12—H12C	109.5
C3—C4—H4	120.0	H12B—C12—H12C	109.5
C5—C4—H4	120.0	N3—C13—S1	178.7 (6)
C6—C5—C4	118.3 (7)	O3—C14—O2	122.9 (5)
C6—C5—H5	120.9	O3—C14—C15	120.9 (5)
C4—C5—H5	120.9	O2—C14—C15	116.2 (6)
C5—C6—C1	122.9 (8)	C14—C15—H15A	109.5
C5—C6—H6	118.6	C14—C15—H15B	109.5
C1—C6—H6	118.6	H15A—C15—H15B	109.5
N1—C7—C1	127.8 (6)	C14—C15—H15C	109.5
N1—C7—H7	116.1	H15A—C15—H15C	109.5
C1—C7—H7	116.1	H15B—C15—H15C	109.5
N1—C8—C9	111.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3i	0.91	1.81	2.703 (6)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3i	0.91	1.81	2.703 (6)	168

Symmetry code: (i) .