Bromido{N-methyl-N'-[1-(2-pyrid-yl)ethyl-idene]ethane-1,2-diamine-κN,N',N''}-(thio-cyanato-κN)-copper(II).

In the title mononuclear copper(II) compound, [CuBr(NCS)(C(10)H(15)N(3))], the Cu(II) atom is five-coordinated by three N atoms of the Schiff base ligand, the N atom of a thio-cyanate ligand and by one bromide ion forming a distorted square-pyramidal geometry. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯Br hydrogen bonds into chains propagating along [101].

Related literature

For general background to Schiff base–copper(II) complexes, see: Adhikary et al. (2009 ▶); Al-Karawi (2009 ▶); Xiao & Zhang (2009 ▶); Rajasekar et al. (2010 ▶); Sang & Lin (2010 ▶); Qin et al. (2010 ▶). For related copper complexes with square-pyramidal coordination, see: Wang et al. (2010 ▶); Zhang et al. (2009 ▶); Wei et al. (2007 ▶).

Experimental

Crystal data

[CuBr(NCS)(C10H15N3)]

M = 378.78

Monoclinic,

a = 10.979 (2) Å

b = 11.407 (2) Å

c = 12.001 (3) Å

β = 109.033 (2)°

V = 1420.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 4.48 mm−1

T = 298 K

0.30 × 0.27 × 0.27 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.347, T max = 0.377

8078 measured reflections

3022 independent reflections

1892 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.137

S = 0.97

3022 reflections

168 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.86 e Å−3

Δρmin = −1.01 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/S1600536810027534/ci5132sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027534/ci5132Isup2.hkl

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

[CuBr(NCS)(C10H15N3)]	F(000) = 756
Mr = 378.78	Dx = 1.771 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2570 reflections
a = 10.979 (2) Å	θ = 2.5–26.5°
b = 11.407 (2) Å	µ = 4.48 mm−1
c = 12.001 (3) Å	T = 298 K
β = 109.033 (2)°	Block, blue
V = 1420.8 (5) Å3	0.30 × 0.27 × 0.27 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3022 independent reflections
Radiation source: fine-focus sealed tube	1892 reflections with I > 2σ(I)
graphite	Rint = 0.070
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −13→14
Tmin = 0.347, Tmax = 0.377	k = −14→12
8078 measured reflections	l = −15→8

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ2(Fo2) + (0.068P)2] where P = (Fo2 + 2Fc2)/3
3022 reflections	(Δ/σ)max = 0.001
168 parameters	Δρmax = 0.86 e Å−3
1 restraint	Δρmin = −1.01 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
Cu1	0.18062 (6)	0.60367 (6)	0.05737 (6)	0.0319 (2)
Br1	0.38736 (6)	0.64845 (6)	0.25208 (5)	0.0412 (2)
N1	0.2487 (4)	0.4486 (4)	0.0218 (4)	0.0292 (11)
N2	0.2631 (5)	0.6533 (5)	−0.0577 (4)	0.0356 (12)
N3	0.1033 (5)	0.7682 (4)	0.0253 (4)	0.0405 (13)
N4	0.0715 (5)	0.5412 (5)	0.1429 (5)	0.0451 (14)
S1	−0.03147 (18)	0.50606 (17)	0.32203 (16)	0.0522 (5)
C1	0.2396 (6)	0.3440 (5)	0.0690 (5)	0.0390 (15)
H1	0.1917	0.3382	0.1200	0.047*
C2	0.2974 (7)	0.2460 (6)	0.0456 (7)	0.0527 (19)
H2	0.2893	0.1748	0.0803	0.063*
C3	0.3683 (7)	0.2534 (6)	−0.0307 (6)	0.0528 (19)
H3	0.4090	0.1874	−0.0474	0.063*
C4	0.3778 (6)	0.3601 (6)	−0.0815 (6)	0.0454 (17)
H4	0.4249	0.3672	−0.1330	0.054*
C5	0.3152 (5)	0.4572 (5)	−0.0541 (5)	0.0314 (13)
C6	0.3174 (5)	0.5760 (5)	−0.1021 (5)	0.0331 (14)
C7	0.3743 (7)	0.5979 (6)	−0.1975 (6)	0.0519 (18)
H7A	0.3179	0.5672	−0.2706	0.078*
H7B	0.4566	0.5597	−0.1780	0.078*
H7C	0.3851	0.6806	−0.2052	0.078*
C8	0.2442 (7)	0.7750 (6)	−0.0943 (6)	0.0518 (18)
H8A	0.1787	0.7814	−0.1712	0.062*
H8B	0.3238	0.8082	−0.0987	0.062*
C9	0.2019 (7)	0.8386 (6)	−0.0024 (6)	0.0535 (19)
H9A	0.2752	0.8504	0.0683	0.064*
H9B	0.1669	0.9148	−0.0322	0.064*
C10	0.0578 (8)	0.8231 (6)	0.1167 (6)	0.064 (2)
H10A	0.1306	0.8425	0.1842	0.096*
H10B	0.0030	0.7692	0.1395	0.096*
H10C	0.0104	0.8931	0.0855	0.096*
C11	0.0286 (5)	0.5262 (5)	0.2159 (5)	0.0312 (14)
H3A	0.038 (5)	0.760 (6)	−0.043 (3)	0.080*

	U11	U22	U33	U12	U13	U23
Cu1	0.0334 (4)	0.0328 (4)	0.0350 (4)	0.0035 (3)	0.0184 (3)	0.0024 (3)
Br1	0.0369 (4)	0.0467 (4)	0.0389 (4)	0.0031 (3)	0.0108 (3)	−0.0090 (3)
N1	0.028 (3)	0.034 (3)	0.029 (3)	−0.001 (2)	0.014 (2)	0.000 (2)
N2	0.030 (3)	0.042 (3)	0.036 (3)	0.004 (2)	0.013 (2)	0.011 (2)
N3	0.049 (3)	0.030 (3)	0.043 (3)	0.007 (2)	0.014 (3)	−0.003 (2)
N4	0.039 (3)	0.056 (4)	0.050 (3)	0.000 (3)	0.028 (3)	0.000 (3)
S1	0.0599 (12)	0.0548 (11)	0.0570 (11)	−0.0083 (9)	0.0397 (10)	−0.0003 (9)
C1	0.041 (4)	0.036 (4)	0.040 (4)	−0.001 (3)	0.015 (3)	0.003 (3)
C2	0.052 (5)	0.029 (4)	0.071 (5)	0.001 (3)	0.012 (4)	−0.003 (3)
C3	0.055 (5)	0.040 (5)	0.057 (5)	0.006 (3)	0.009 (4)	−0.016 (4)
C4	0.039 (4)	0.058 (5)	0.042 (4)	0.006 (3)	0.017 (3)	−0.016 (3)
C5	0.026 (3)	0.039 (4)	0.028 (3)	0.001 (3)	0.008 (3)	−0.002 (3)
C6	0.023 (3)	0.050 (4)	0.029 (3)	0.002 (3)	0.013 (2)	0.007 (3)
C7	0.046 (4)	0.077 (5)	0.041 (4)	0.002 (4)	0.026 (3)	0.013 (4)
C8	0.056 (5)	0.046 (5)	0.066 (5)	0.006 (3)	0.036 (4)	0.020 (4)
C9	0.055 (5)	0.033 (4)	0.065 (5)	0.002 (3)	0.008 (4)	0.008 (3)
C10	0.079 (6)	0.060 (5)	0.054 (5)	0.026 (4)	0.022 (4)	−0.008 (4)
C11	0.022 (3)	0.029 (3)	0.044 (4)	0.000 (2)	0.012 (3)	−0.006 (3)

Cu1—N4	1.949 (5)	C3—C4	1.380 (9)
Cu1—N2	1.965 (5)	C3—H3	0.93
Cu1—N1	2.019 (5)	C4—C5	1.398 (8)
Cu1—N3	2.044 (5)	C4—H4	0.93
Cu1—Br1	2.7228 (10)	C5—C6	1.476 (8)
N1—C1	1.338 (7)	C6—C7	1.494 (8)
N1—C5	1.343 (7)	C7—H7A	0.96
N2—C6	1.274 (7)	C7—H7B	0.96
N2—C8	1.451 (8)	C7—H7C	0.96
N3—C9	1.470 (9)	C8—C9	1.514 (9)
N3—C10	1.484 (8)	C8—H8A	0.97
N3—H3A	0.899 (10)	C8—H8B	0.97
N4—C11	1.135 (7)	C9—H9A	0.97
S1—C11	1.630 (7)	C9—H9B	0.97
C1—C2	1.359 (9)	C10—H10A	0.96
C1—H1	0.93	C10—H10B	0.96
C2—C3	1.384 (10)	C10—H10C	0.96
C2—H2	0.93
N4—Cu1—N2	168.1 (2)	C3—C4—H4	120.6
N4—Cu1—N1	97.2 (2)	C5—C4—H4	120.6
N2—Cu1—N1	79.4 (2)	N1—C5—C4	121.3 (6)
N4—Cu1—N3	98.4 (2)	N1—C5—C6	114.4 (5)
N2—Cu1—N3	82.0 (2)	C4—C5—C6	124.3 (6)
N1—Cu1—N3	157.5 (2)	N2—C6—C5	113.7 (5)
N4—Cu1—Br1	95.75 (16)	N2—C6—C7	125.1 (6)
N2—Cu1—Br1	95.90 (14)	C5—C6—C7	121.1 (6)
N1—Cu1—Br1	94.79 (12)	C6—C7—H7A	109.5
N3—Cu1—Br1	99.67 (15)	C6—C7—H7B	109.5
C1—N1—C5	118.9 (5)	H7A—C7—H7B	109.5
C1—N1—Cu1	127.4 (4)	C6—C7—H7C	109.5
C5—N1—Cu1	113.6 (4)	H7A—C7—H7C	109.5
C6—N2—C8	125.1 (5)	H7B—C7—H7C	109.5
C6—N2—Cu1	118.7 (4)	N2—C8—C9	106.6 (5)
C8—N2—Cu1	115.8 (4)	N2—C8—H8A	110.4
C9—N3—C10	112.8 (5)	C9—C8—H8A	110.4
C9—N3—Cu1	104.6 (4)	N2—C8—H8B	110.4
C10—N3—Cu1	117.9 (4)	C9—C8—H8B	110.4
C9—N3—H3A	106 (5)	H8A—C8—H8B	108.6
C10—N3—H3A	111 (5)	N3—C9—C8	109.1 (5)
Cu1—N3—H3A	104 (5)	N3—C9—H9A	109.9
C11—N4—Cu1	160.6 (5)	C8—C9—H9A	109.9
N1—C1—C2	122.8 (6)	N3—C9—H9B	109.9
N1—C1—H1	118.6	C8—C9—H9B	109.9
C2—C1—H1	118.6	H9A—C9—H9B	108.3
C1—C2—C3	119.2 (7)	N3—C10—H10A	109.5
C1—C2—H2	120.4	N3—C10—H10B	109.5
C3—C2—H2	120.4	H10A—C10—H10B	109.5
C4—C3—C2	119.1 (6)	N3—C10—H10C	109.5
C4—C3—H3	120.5	H10A—C10—H10C	109.5
C2—C3—H3	120.5	H10B—C10—H10C	109.5
C3—C4—C5	118.7 (6)	N4—C11—S1	179.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···Br1i	0.90 (1)	2.69 (4)	3.494 (5)	150 (6)

Table 1

Selected bond lengths (Å)

Cu1—N4	1.949 (5)
Cu1—N2	1.965 (5)
Cu1—N1	2.019 (5)
Cu1—N3	2.044 (5)
Cu1—Br1	2.7228 (10)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯Br1i	0.90 (1)	2.69 (4)	3.494 (5)	150 (6)

Symmetry code: (i) .