{4-Bromo-2-[2-(methyl-amino-)ethyl-iminometh-yl]phenolato}thio-cyanato-copper(II).

In the title mononuclear copper(II) complex, [Cu(C(10)H(12)BrN(2)O)(NCS)], the Cu(II) ion is coordinated by two N atoms and one O atom from a Schiff base ligand, and by one N atom from a thio-cyanate anion, giving a square-planar geometry. In the crystal structure, symmetry-related mol-ecules are linked by an N-H⋯S hydrogen bond.

Related literature

For related literature, see: Diao & Li (2007 ▶); Diao et al. (2007 ▶); Ma et al. (2005 ▶); Ma, Gu et al. (2006 ▶); Ma, Lv et al. (2006 ▶); Ma, Wu et al. (2006 ▶); Wei et al. (2007 ▶).

Experimental

Crystal data

[Cu(C10H12BrN2O)(NCS)]

M = 377.75

Monoclinic,

a = 5.952 (3) Å

b = 19.660 (3) Å

c = 12.718 (2) Å

β = 94.331 (3)°

V = 1484.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 4.30 mm−1

T = 298 (2) K

0.32 × 0.32 × 0.31 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.259, T max = 0.267

11246 measured reflections

2997 independent reflections

1875 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.180

S = 1.11

2997 reflections

164 parameters

H-atom parameters constrained

Δρmax = 1.68 e Å−3

Δρmin = −0.84 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016589/su2051sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016589/su2051Isup2.hkl

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

[Cu(C10H12BrN2O)(NCS)]	F000 = 748
Mr = 377.75	Dx = 1.691 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1708 reflections
a = 5.952 (3) Å	θ = 2.5–25.3º
b = 19.660 (3) Å	µ = 4.30 mm−1
c = 12.718 (2) Å	T = 298 (2) K
β = 94.331 (3)º	Block, blue
V = 1484.0 (8) Å3	0.32 × 0.32 × 0.31 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2997 independent reflections
Radiation source: fine-focus sealed tube	1875 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.071
T = 298(2) K	θmax = 26.5º
ω scan	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.259, Tmax = 0.267	k = −24→24
11246 measured reflections	l = −15→15

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)] = 0.076	H-atom parameters constrained
wR(F2) = 0.181	w = 1/[σ2(Fo2) + (0.0672P)2 + 4.7203P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
2997 reflections	Δρmax = 1.68 e Å−3
164 parameters	Δρmin = −0.84 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	0.77313 (15)	0.20764 (5)	0.04645 (8)	0.0407 (3)
N1	1.0514 (10)	0.1635 (3)	0.0963 (5)	0.0392 (15)
N2	0.8291 (12)	0.2634 (4)	0.1796 (7)	0.058 (2)
H2A	0.7645	0.2393	0.2304	0.070*
N3	0.4927 (12)	0.2539 (4)	0.0002 (6)	0.053 (2)
O1	0.7104 (8)	0.1410 (3)	−0.0588 (4)	0.0460 (14)
S1	0.0695 (4)	0.29376 (15)	−0.0863 (2)	0.0664 (8)
Br1	1.31654 (16)	−0.06412 (5)	−0.23999 (9)	0.0633 (4)
C1	1.1328 (13)	0.0028 (4)	−0.1792 (7)	0.044 (2)
C2	0.9203 (14)	0.0131 (4)	−0.2253 (8)	0.049 (2)
H2	0.8712	−0.0121	−0.2845	0.059*
C3	0.7799 (13)	0.0596 (4)	−0.1860 (7)	0.047 (2)
H3	0.6360	0.0657	−0.2184	0.057*
C4	0.8518 (13)	0.0994 (4)	−0.0946 (6)	0.0367 (18)
C5	1.0688 (12)	0.0860 (4)	−0.0492 (6)	0.0369 (18)
C6	1.2068 (14)	0.0376 (4)	−0.0913 (7)	0.045 (2)
H6	1.3497	0.0291	−0.0592	0.054*
C7	1.1533 (13)	0.1183 (4)	0.0480 (7)	0.042 (2)
H7	1.2941	0.1047	0.0773	0.051*
C8	1.1509 (15)	0.1902 (5)	0.1982 (7)	0.052 (2)
H8A	1.3140	0.1889	0.1997	0.062*
H8B	1.1038	0.1625	0.2557	0.062*
C9	1.0734 (14)	0.2612 (5)	0.2099 (7)	0.051 (2)
H9A	1.1028	0.2760	0.2824	0.061*
H9B	1.1531	0.2912	0.1650	0.061*
C10	0.7370 (17)	0.3305 (6)	0.1855 (10)	0.083 (4)
H10A	0.8001	0.3526	0.2482	0.125*
H10B	0.5763	0.3276	0.1874	0.125*
H10C	0.7728	0.3562	0.1248	0.125*
C11	0.3146 (15)	0.2696 (4)	−0.0378 (7)	0.048 (2)

	U11	U22	U33	U12	U13	U23
Cu1	0.0271 (5)	0.0511 (6)	0.0429 (6)	0.0011 (4)	−0.0028 (4)	−0.0086 (5)
N1	0.028 (3)	0.047 (4)	0.041 (4)	−0.004 (3)	−0.006 (3)	−0.001 (3)
N2	0.040 (4)	0.062 (5)	0.070 (5)	−0.001 (4)	−0.005 (4)	−0.022 (4)
N3	0.030 (4)	0.069 (5)	0.058 (5)	0.008 (3)	−0.006 (3)	−0.015 (4)
O1	0.025 (3)	0.055 (4)	0.056 (4)	0.006 (3)	−0.009 (2)	−0.012 (3)
S1	0.0412 (13)	0.0813 (18)	0.0744 (18)	0.0000 (13)	−0.0115 (12)	0.0316 (15)
Br1	0.0480 (6)	0.0520 (6)	0.0910 (8)	0.0037 (4)	0.0131 (5)	−0.0149 (5)
C1	0.036 (4)	0.030 (4)	0.068 (6)	0.003 (3)	0.014 (4)	−0.002 (4)
C2	0.035 (5)	0.045 (5)	0.066 (6)	−0.005 (4)	0.001 (4)	−0.009 (4)
C3	0.029 (4)	0.047 (5)	0.064 (6)	0.000 (4)	−0.014 (4)	−0.007 (4)
C4	0.031 (4)	0.033 (4)	0.044 (5)	0.001 (3)	−0.006 (3)	−0.002 (4)
C5	0.029 (4)	0.040 (4)	0.041 (5)	0.004 (3)	0.004 (3)	0.013 (4)
C6	0.042 (5)	0.037 (4)	0.057 (5)	0.000 (4)	−0.002 (4)	0.007 (4)
C7	0.028 (4)	0.043 (5)	0.055 (5)	0.003 (4)	−0.007 (4)	0.015 (4)
C8	0.048 (5)	0.065 (6)	0.039 (5)	−0.011 (4)	−0.017 (4)	−0.003 (4)
C9	0.039 (5)	0.075 (6)	0.038 (5)	−0.006 (4)	−0.002 (4)	−0.022 (5)
C10	0.051 (6)	0.092 (8)	0.106 (9)	0.038 (6)	−0.005 (6)	−0.039 (7)
C11	0.042 (5)	0.051 (5)	0.050 (5)	−0.015 (4)	−0.001 (4)	−0.004 (4)

Cu1—O1	1.890 (5)	C2—H2	0.9300
Cu1—N1	1.934 (6)	C3—C4	1.439 (11)
Cu1—N3	1.952 (7)	C3—H3	0.9300
Cu1—N2	2.024 (7)	C4—C5	1.399 (10)
N1—C7	1.262 (10)	C5—C6	1.390 (11)
N1—C8	1.479 (10)	C5—C7	1.446 (12)
N2—C10	1.432 (12)	C6—H6	0.9300
N2—C9	1.476 (11)	C7—H7	0.9300
N2—H2A	0.9100	C8—C9	1.481 (12)
N3—C11	1.172 (11)	C8—H8A	0.9700
O1—C4	1.282 (9)	C8—H8B	0.9700
S1—C11	1.612 (10)	C9—H9A	0.9700
Br1—C1	1.911 (8)	C9—H9B	0.9700
C1—C6	1.356 (12)	C10—H10A	0.9600
C1—C2	1.368 (12)	C10—H10B	0.9600
C2—C3	1.358 (12)	C10—H10C	0.9600
O1—Cu1—N1	92.3 (3)	C6—C5—C4	121.6 (8)
O1—Cu1—N3	89.5 (3)	C6—C5—C7	116.9 (7)
N1—Cu1—N3	178.1 (3)	C4—C5—C7	121.4 (7)
O1—Cu1—N2	168.3 (3)	C1—C6—C5	119.9 (8)
N1—Cu1—N2	83.4 (3)	C1—C6—H6	120.1
N3—Cu1—N2	94.7 (3)	C5—C6—H6	120.1
C7—N1—C8	120.0 (7)	N1—C7—C5	125.2 (7)
C7—N1—Cu1	126.0 (5)	N1—C7—H7	117.4
C8—N1—Cu1	113.9 (5)	C5—C7—H7	117.4
C10—N2—C9	112.8 (8)	N1—C8—C9	108.4 (7)
C10—N2—Cu1	120.2 (7)	N1—C8—H8A	110.0
C9—N2—Cu1	107.4 (5)	C9—C8—H8A	110.0
C10—N2—H2A	105.0	N1—C8—H8B	110.0
C9—N2—H2A	105.0	C9—C8—H8B	110.0
Cu1—N2—H2A	105.0	H8A—C8—H8B	108.4
C11—N3—Cu1	166.5 (7)	N2—C9—C8	108.1 (7)
C4—O1—Cu1	126.5 (5)	N2—C9—H9A	110.1
C6—C1—C2	120.7 (8)	C8—C9—H9A	110.1
C6—C1—Br1	121.4 (6)	N2—C9—H9B	110.1
C2—C1—Br1	117.9 (7)	C8—C9—H9B	110.1
C3—C2—C1	121.1 (8)	H9A—C9—H9B	108.4
C3—C2—H2	119.4	N2—C10—H10A	109.5
C1—C2—H2	119.4	N2—C10—H10B	109.5
C2—C3—C4	120.6 (7)	H10A—C10—H10B	109.5
C2—C3—H3	119.7	N2—C10—H10C	109.5
C4—C3—H3	119.7	H10A—C10—H10C	109.5
O1—C4—C5	125.7 (7)	H10B—C10—H10C	109.5
O1—C4—C3	118.1 (7)	N3—C11—S1	177.5 (9)
C5—C4—C3	116.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1i	0.91	2.76	3.635 (9)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S1i	0.91	2.76	3.635 (9)	162

Symmetry code: (i) .