{2-Bromo-4-chloro-6-[2-(diethyl-amino)ethyl-imino-meth-yl]phenolato-κN,N',O}(thio-cyanato-κN)copper(II).

In the title compound, [Cu(C(13)H(17)BrClN(2)O)(NCS)], the Cu atom is in a slightly distorted square-planar geometry, coordinated by the three donor atoms of the ligand and the N atom of the isothio-cyanate group.

Related literature

For the biological activity of Schiff base compounds, see: Panneerselvam et al. (2005 ▶); Shi et al. (2007 ▶); Singh et al. (2006 ▶, 2007 ▶); Zhong et al. (2006 ▶).

Experimental

Crystal data

[Cu(C13H17BrClN2O)(NCS)]

M = 454.27

Monoclinic,

a = 8.651 (2) Å

b = 14.137 (2) Å

c = 14.145 (2) Å

β = 90.820 (2)°

V = 1729.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.85 mm−1

T = 293 (2) K

0.17 × 0.13 × 0.13 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.561, T max = 0.634

14228 measured reflections

3745 independent reflections

2784 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.123

S = 1.04

3745 reflections

201 parameters

H-atom parameters constrained

Δρmax = 1.22 e Å−3

Δρmin = −0.92 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063908/sg2212sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063908/sg2212Isup2.hkl

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

[Cu(C13H17BrClN2O)(NCS)]	F000 = 908
Mr = 454.27	Dx = 1.744 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
a = 8.651 (2) Å	Cell parameters from 3721 reflections
b = 14.137 (2) Å	θ = 2.5–25.3º
c = 14.145 (2) Å	µ = 3.85 mm−1
β = 90.820 (2)º	T = 293 (2) K
V = 1729.7 (5) Å3	Block, blue
Z = 4	0.17 × 0.13 × 0.13 mm

Bruker SMART 1K CCD area-detector diffractometer	3745 independent reflections
Radiation source: fine-focus sealed tube	2784 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 293(2) K	θmax = 27.0º
ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −11→10
Tmin = 0.561, Tmax = 0.634	k = −18→17
14228 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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0599P)2 + 1.7229P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3745 reflections	Δρmax = 1.22 e Å−3
201 parameters	Δρmin = −0.92 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
Cu1	0.13650 (6)	0.16708 (3)	0.07012 (3)	0.03921 (16)
O1	−0.0067 (4)	0.2249 (2)	−0.0153 (2)	0.0503 (8)
N1	0.1195 (4)	0.2692 (3)	0.1611 (2)	0.0424 (8)
N2	0.3230 (4)	0.1260 (3)	0.1541 (2)	0.0436 (8)
N3	0.1631 (4)	0.0684 (3)	−0.0241 (3)	0.0478 (9)
Br1	−0.22122 (6)	0.25006 (4)	−0.17829 (3)	0.05842 (18)
Cl1	−0.33341 (16)	0.58720 (9)	0.00426 (11)	0.0698 (4)
S1	0.10508 (13)	−0.05745 (9)	−0.17046 (8)	0.0502 (3)
C1	−0.0783 (5)	0.3037 (3)	−0.0054 (3)	0.0410 (9)
C2	−0.0611 (5)	0.3662 (3)	0.0729 (3)	0.0422 (9)
C3	−0.1405 (5)	0.4526 (3)	0.0746 (3)	0.0518 (11)
H3	−0.1269	0.4932	0.1258	0.062*
C4	−0.2375 (5)	0.4777 (3)	0.0021 (3)	0.0530 (11)
C5	−0.2594 (5)	0.4179 (4)	−0.0741 (3)	0.0520 (11)
H5	−0.3259	0.4352	−0.1234	0.062*
C6	−0.1840 (5)	0.3339 (3)	−0.0770 (3)	0.0423 (9)
C7	0.0380 (5)	0.3446 (3)	0.1520 (3)	0.0481 (11)
H7	0.0437	0.3887	0.2007	0.058*
C8	0.2151 (6)	0.2587 (4)	0.2462 (3)	0.0635 (15)
H8A	0.2973	0.3053	0.2463	0.076*
H8B	0.1528	0.2689	0.3018	0.076*
C9	0.2793 (9)	0.1661 (4)	0.2487 (4)	0.087 (2)
H9A	0.2051	0.1239	0.2774	0.104*
H9B	0.3707	0.1671	0.2891	0.104*
C10	0.3261 (6)	0.0234 (3)	0.1647 (4)	0.0616 (13)
H10A	0.3399	−0.0041	0.1026	0.074*
H10B	0.2257	0.0034	0.1868	0.074*
C11	0.4495 (6)	−0.0183 (4)	0.2313 (4)	0.0676 (15)
H11A	0.5491	0.0064	0.2151	0.101*
H11B	0.4503	−0.0859	0.2251	0.101*
H11C	0.4265	−0.0015	0.2953	0.101*
C12	0.4629 (7)	0.1734 (6)	0.1237 (5)	0.098 (2)
H12A	0.4500	0.2405	0.1354	0.118*
H12B	0.5472	0.1519	0.1642	0.118*
C13	0.5091 (7)	0.1627 (7)	0.0301 (5)	0.117 (3)
H13A	0.5228	0.0968	0.0164	0.175*
H13B	0.6049	0.1955	0.0211	0.175*
H13C	0.4314	0.1885	−0.0116	0.175*
C14	0.1359 (4)	0.0175 (3)	−0.0848 (3)	0.0380 (9)

	U11	U22	U33	U12	U13	U23
Cu1	0.0451 (3)	0.0384 (3)	0.0339 (3)	−0.0012 (2)	−0.0085 (2)	−0.0047 (2)
O1	0.069 (2)	0.0402 (17)	0.0409 (17)	0.0084 (15)	−0.0189 (14)	−0.0043 (13)
N1	0.045 (2)	0.051 (2)	0.0313 (17)	−0.0048 (17)	−0.0055 (15)	−0.0080 (15)
N2	0.044 (2)	0.043 (2)	0.0443 (19)	−0.0070 (16)	−0.0090 (15)	0.0003 (15)
N3	0.051 (2)	0.051 (2)	0.0413 (19)	0.0001 (17)	−0.0050 (16)	−0.0100 (17)
Br1	0.0689 (3)	0.0642 (3)	0.0418 (3)	−0.0017 (2)	−0.0130 (2)	0.0037 (2)
Cl1	0.0715 (9)	0.0532 (7)	0.0852 (9)	0.0218 (6)	0.0219 (7)	0.0123 (7)
S1	0.0508 (6)	0.0547 (7)	0.0451 (6)	−0.0034 (5)	−0.0002 (5)	−0.0178 (5)
C1	0.043 (2)	0.040 (2)	0.040 (2)	−0.0047 (18)	0.0020 (17)	0.0054 (18)
C2	0.042 (2)	0.043 (2)	0.042 (2)	0.0003 (18)	0.0053 (18)	−0.0017 (18)
C3	0.058 (3)	0.043 (3)	0.055 (3)	0.001 (2)	0.012 (2)	−0.003 (2)
C4	0.051 (3)	0.048 (3)	0.061 (3)	0.011 (2)	0.016 (2)	0.010 (2)
C5	0.045 (3)	0.059 (3)	0.052 (3)	0.006 (2)	0.006 (2)	0.016 (2)
C6	0.042 (2)	0.047 (2)	0.038 (2)	−0.0041 (19)	0.0026 (17)	0.0073 (18)
C7	0.051 (3)	0.050 (3)	0.043 (2)	−0.007 (2)	0.0018 (19)	−0.013 (2)
C8	0.055 (3)	0.096 (4)	0.039 (2)	0.008 (3)	−0.015 (2)	−0.013 (2)
C9	0.134 (6)	0.071 (4)	0.055 (3)	0.032 (4)	−0.044 (3)	−0.016 (3)
C10	0.054 (3)	0.043 (3)	0.087 (4)	0.008 (2)	−0.026 (3)	−0.004 (2)
C11	0.062 (3)	0.058 (3)	0.082 (4)	0.014 (3)	−0.027 (3)	0.001 (3)
C12	0.057 (4)	0.145 (7)	0.090 (5)	−0.029 (4)	−0.017 (3)	0.032 (4)
C13	0.060 (4)	0.196 (9)	0.095 (5)	−0.015 (5)	0.020 (4)	−0.066 (6)
C14	0.032 (2)	0.040 (2)	0.042 (2)	0.0029 (17)	−0.0011 (16)	0.0012 (18)

Cu1—O1	1.902 (3)	C5—C6	1.356 (6)
Cu1—N1	1.940 (3)	C5—H5	0.9300
Cu1—N3	1.945 (4)	C7—H7	0.9300
Cu1—N2	2.073 (3)	C8—C9	1.422 (7)
O1—C1	1.283 (5)	C8—H8A	0.9700
N1—C7	1.284 (6)	C8—H8B	0.9700
N1—C8	1.458 (5)	C9—H9A	0.9700
N2—C12	1.454 (7)	C9—H9B	0.9700
N2—C10	1.457 (6)	C10—C11	1.532 (6)
N2—C9	1.507 (7)	C10—H10A	0.9700
N3—C14	1.143 (5)	C10—H10B	0.9700
Br1—C6	1.884 (4)	C11—H11A	0.9600
Cl1—C4	1.757 (5)	C11—H11B	0.9600
S1—C14	1.628 (4)	C11—H11C	0.9600
C1—C6	1.421 (6)	C12—C13	1.397 (9)
C1—C2	1.421 (6)	C12—H12A	0.9700
C2—C3	1.402 (6)	C12—H12B	0.9700
C2—C7	1.433 (6)	C13—H13A	0.9600
C3—C4	1.363 (6)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.381 (7)
O1—Cu1—N1	92.66 (14)	C9—C8—N1	109.3 (4)
O1—Cu1—N3	87.45 (14)	C9—C8—H8A	109.8
N1—Cu1—N3	176.83 (16)	N1—C8—H8A	109.8
O1—Cu1—N2	168.15 (14)	C9—C8—H8B	109.8
N1—Cu1—N2	83.93 (14)	N1—C8—H8B	109.8
N3—Cu1—N2	95.33 (15)	H8A—C8—H8B	108.3
C1—O1—Cu1	127.9 (3)	C8—C9—N2	115.3 (5)
C7—N1—C8	118.1 (4)	C8—C9—H9A	108.4
C7—N1—Cu1	126.7 (3)	N2—C9—H9A	108.4
C8—N1—Cu1	115.1 (3)	C8—C9—H9B	108.4
C12—N2—C10	118.3 (5)	N2—C9—H9B	108.4
C12—N2—C9	108.0 (5)	H9A—C9—H9B	107.5
C10—N2—C9	106.7 (4)	N2—C10—C11	117.3 (4)
C12—N2—Cu1	110.2 (3)	N2—C10—H10A	108.0
C10—N2—Cu1	110.5 (3)	C11—C10—H10A	108.0
C9—N2—Cu1	101.5 (3)	N2—C10—H10B	108.0
C14—N3—Cu1	160.4 (3)	C11—C10—H10B	108.0
O1—C1—C6	119.3 (4)	H10A—C10—H10B	107.2
O1—C1—C2	125.4 (4)	C10—C11—H11A	109.5
C6—C1—C2	115.3 (4)	C10—C11—H11B	109.5
C3—C2—C1	120.6 (4)	H11A—C11—H11B	109.5
C3—C2—C7	117.4 (4)	C10—C11—H11C	109.5
C1—C2—C7	122.0 (4)	H11A—C11—H11C	109.5
C4—C3—C2	120.7 (4)	H11B—C11—H11C	109.5
C4—C3—H3	119.7	C13—C12—N2	118.8 (6)
C2—C3—H3	119.7	C13—C12—H12A	107.6
C3—C4—C5	120.3 (4)	N2—C12—H12A	107.6
C3—C4—Cl1	120.1 (4)	C13—C12—H12B	107.6
C5—C4—Cl1	119.6 (4)	N2—C12—H12B	107.6
C6—C5—C4	119.9 (4)	H12A—C12—H12B	107.1
C6—C5—H5	120.0	C12—C13—H13A	109.5
C4—C5—H5	120.0	C12—C13—H13B	109.5
C5—C6—C1	123.1 (4)	H13A—C13—H13B	109.5
C5—C6—Br1	119.8 (3)	C12—C13—H13C	109.5
C1—C6—Br1	117.1 (3)	H13A—C13—H13C	109.5
N1—C7—C2	125.2 (4)	H13B—C13—H13C	109.5
N1—C7—H7	117.4	N3—C14—S1	177.3 (4)
C2—C7—H7	117.4

Cu1—O1	1.902 (3)
Cu1—N1	1.940 (3)
Cu1—N3	1.945 (4)
Cu1—N2	2.073 (3)

O1—Cu1—N1	92.66 (14)
O1—Cu1—N3	87.45 (14)
N1—Cu1—N3	176.83 (16)
O1—Cu1—N2	168.15 (14)
N1—Cu1—N2	83.93 (14)
N3—Cu1—N2	95.33 (15)