Bis[4-bromo-2-(cyclo-pentyl-imino-meth-yl)phenolato]copper(II).

The title compound, [Cu(C(12)H(13)BrNO)(2)], was prepared by the reaction of 5-bromo-salicylaldehyde, cyclo-pentyl-amine and copper(II) acetate in an ethanol solution. The Cu(II) atom lies on an inversion center and is four-coordinated in a square-planar geometry by two N and two O atoms from two 4-bromo-2-(cyclo-pentyl-imino-meth-yl)phenolate Schiff base ligands.

Related literature

For background on Schiff base complexes, see: Costes et al. (2002 ▶); Erxleben (2001 ▶); Lacroix et al. (1996 ▶); Odoko et al. (2006 ▶); Ali et al. (2006 ▶). For related copper(II) complexes, see: Wang et al. (2007 ▶); Datta et al. (2008 ▶); Yusnita et al. (2008 ▶); Wang & Zheng (2007 ▶). For a related zinc(II) complex, see: Cai (2009 ▶).

Experimental

Crystal data

[Cu(C12H13BrNO)2]

M = 597.83

Monoclinic,

a = 9.190 (2) Å

b = 10.960 (2) Å

c = 12.166 (2) Å

β = 109.73 (3)°

V = 1153.5 (4) Å3

Z = 2

Mo Kα radiation

μ = 4.44 mm−1

T = 298 K

0.27 × 0.23 × 0.23 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.381, T max = 0.429 (expected range = 0.320–0.361)

9709 measured reflections

2636 independent reflections

2003 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.098

S = 1.02

2636 reflections

142 parameters

H-atom parameters constrained

Δρmax = 0.93 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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/S1600536809006606/su2099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006606/su2099Isup2.hkl

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

[Cu(C12H13BrNO)2]	F(000) = 598
Mr = 597.83	Dx = 1.721 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.190 (2) Å	Cell parameters from 2505 reflections
b = 10.960 (2) Å	θ = 2.3–25.0°
c = 12.166 (2) Å	µ = 4.43 mm−1
β = 109.73 (3)°	T = 298 K
V = 1153.5 (4) Å3	Block, blue
Z = 2	0.27 × 0.23 × 0.23 mm

Bruker SMART 1000 CCD area-detector diffractometer	2636 independent reflections
Radiation source: fine-focus sealed tube	2003 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.381, Tmax = 0.429	k = −14→14
9709 measured reflections	l = −15→15

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0427P)2 + 0.9221P] where P = (Fo2 + 2Fc2)/3
2636 reflections	(Δ/σ)max = 0.001
142 parameters	Δρmax = 0.93 e Å−3
0 restraints	Δρmin = −0.41 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	0.0000	1.0000	0.0000	0.03400 (16)
Br1	−0.34783 (5)	0.60773 (4)	0.33661 (4)	0.06123 (17)
O1	−0.0883 (3)	1.00623 (19)	0.1197 (2)	0.0446 (6)
N1	0.0534 (3)	0.8203 (2)	0.0328 (2)	0.0341 (6)
C1	−0.1071 (4)	0.7941 (3)	0.1548 (3)	0.0344 (7)
C2	−0.1456 (4)	0.9175 (3)	0.1630 (3)	0.0348 (7)
C3	−0.2475 (4)	0.9435 (3)	0.2236 (3)	0.0435 (8)
H3	−0.2753	1.0242	0.2294	0.052*
C4	−0.3073 (4)	0.8541 (3)	0.2744 (3)	0.0465 (9)
H4	−0.3752	0.8741	0.3136	0.056*
C5	−0.2659 (4)	0.7337 (3)	0.2671 (3)	0.0422 (8)
C6	−0.1676 (4)	0.7034 (3)	0.2090 (3)	0.0391 (7)
H6	−0.1404	0.6222	0.2052	0.047*
C7	−0.0063 (4)	0.7551 (3)	0.0935 (3)	0.0374 (7)
H7	0.0184	0.6726	0.0987	0.045*
C8	0.1560 (4)	0.7602 (3)	−0.0219 (3)	0.0386 (7)
H8	0.1265	0.7915	−0.1019	0.046*
C9	0.3252 (4)	0.7923 (4)	0.0374 (4)	0.0603 (11)
H9A	0.3467	0.8740	0.0163	0.072*
H9B	0.3536	0.7874	0.1216	0.072*
C10	0.4115 (5)	0.6976 (5)	−0.0078 (6)	0.0901 (18)
H10A	0.4543	0.7346	−0.0626	0.108*
H10B	0.4955	0.6632	0.0563	0.108*
C11	0.2977 (5)	0.6002 (4)	−0.0671 (4)	0.0642 (12)
H11A	0.3412	0.5199	−0.0429	0.077*
H11B	0.2696	0.6065	−0.1512	0.077*
C12	0.1586 (5)	0.6206 (3)	−0.0307 (4)	0.0507 (9)
H12A	0.1713	0.5824	0.0438	0.061*
H12B	0.0651	0.5900	−0.0889	0.061*

	U11	U22	U33	U12	U13	U23
Cu1	0.0412 (3)	0.0242 (3)	0.0424 (3)	0.0024 (2)	0.0218 (3)	0.0028 (2)
Br1	0.0702 (3)	0.0547 (3)	0.0720 (3)	−0.0114 (2)	0.0414 (2)	0.0125 (2)
O1	0.0659 (16)	0.0251 (11)	0.0570 (15)	0.0009 (11)	0.0395 (13)	0.0012 (10)
N1	0.0374 (14)	0.0263 (13)	0.0425 (15)	0.0034 (11)	0.0185 (12)	0.0018 (11)
C1	0.0377 (17)	0.0294 (16)	0.0387 (17)	0.0018 (13)	0.0163 (14)	0.0037 (13)
C2	0.0401 (18)	0.0290 (15)	0.0373 (17)	0.0023 (13)	0.0159 (14)	0.0031 (13)
C3	0.056 (2)	0.0336 (17)	0.050 (2)	0.0058 (16)	0.0300 (18)	−0.0006 (16)
C4	0.050 (2)	0.049 (2)	0.049 (2)	0.0019 (17)	0.0287 (18)	0.0009 (17)
C5	0.0443 (19)	0.0424 (19)	0.0442 (19)	−0.0079 (15)	0.0205 (16)	0.0070 (15)
C6	0.0461 (19)	0.0289 (16)	0.0441 (19)	−0.0008 (14)	0.0175 (15)	0.0036 (14)
C7	0.0406 (17)	0.0270 (16)	0.0470 (19)	0.0064 (13)	0.0177 (15)	0.0040 (14)
C8	0.0421 (18)	0.0292 (16)	0.0489 (19)	0.0060 (14)	0.0212 (16)	0.0012 (14)
C9	0.043 (2)	0.056 (2)	0.085 (3)	−0.0012 (19)	0.026 (2)	−0.024 (2)
C10	0.051 (3)	0.082 (3)	0.147 (5)	−0.006 (2)	0.046 (3)	−0.051 (4)
C11	0.066 (3)	0.049 (2)	0.085 (3)	0.012 (2)	0.036 (2)	−0.010 (2)
C12	0.059 (2)	0.0349 (19)	0.064 (2)	0.0030 (17)	0.028 (2)	−0.0058 (17)

Cu1—O1i	1.892 (2)	C6—H6	0.9300
Cu1—O1	1.892 (2)	C7—H7	0.9300
Cu1—N1	2.036 (2)	C8—C9	1.518 (5)
Cu1—N1i	2.036 (2)	C8—C12	1.534 (4)
Br1—C5	1.902 (3)	C8—H8	0.9800
O1—C2	1.299 (4)	C9—C10	1.518 (5)
N1—C7	1.278 (4)	C9—H9A	0.9700
N1—C8	1.480 (4)	C9—H9B	0.9700
C1—C6	1.407 (4)	C10—C11	1.498 (6)
C1—C2	1.411 (4)	C10—H10A	0.9700
C1—C7	1.436 (4)	C10—H10B	0.9700
C2—C3	1.403 (4)	C11—C12	1.504 (6)
C3—C4	1.369 (5)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.385 (5)	C12—H12A	0.9700
C4—H4	0.9300	C12—H12B	0.9700
C5—C6	1.362 (5)
O1i—Cu1—O1	180.0	N1—C8—C9	112.9 (3)
O1i—Cu1—N1	88.74 (10)	N1—C8—C12	120.2 (3)
O1—Cu1—N1	91.26 (10)	C9—C8—C12	103.1 (3)
O1i—Cu1—N1i	91.26 (10)	N1—C8—H8	106.6
O1—Cu1—N1i	88.74 (10)	C9—C8—H8	106.6
N1—Cu1—N1i	180.0	C12—C8—H8	106.6
C2—O1—Cu1	128.5 (2)	C10—C9—C8	104.2 (3)
C7—N1—C8	118.3 (3)	C10—C9—H9A	110.9
C7—N1—Cu1	122.1 (2)	C8—C9—H9A	110.9
C8—N1—Cu1	119.42 (19)	C10—C9—H9B	110.9
C6—C1—C2	119.7 (3)	C8—C9—H9B	110.9
C6—C1—C7	117.4 (3)	H9A—C9—H9B	108.9
C2—C1—C7	122.9 (3)	C11—C10—C9	107.3 (3)
O1—C2—C3	119.7 (3)	C11—C10—H10A	110.3
O1—C2—C1	122.9 (3)	C9—C10—H10A	110.3
C3—C2—C1	117.3 (3)	C11—C10—H10B	110.3
C4—C3—C2	122.3 (3)	C9—C10—H10B	110.3
C4—C3—H3	118.9	H10A—C10—H10B	108.5
C2—C3—H3	118.9	C10—C11—C12	106.1 (3)
C3—C4—C5	119.5 (3)	C10—C11—H11A	110.5
C3—C4—H4	120.3	C12—C11—H11A	110.5
C5—C4—H4	120.3	C10—C11—H11B	110.5
C6—C5—C4	120.7 (3)	C12—C11—H11B	110.5
C6—C5—Br1	119.0 (3)	H11A—C11—H11B	108.7
C4—C5—Br1	120.3 (3)	C11—C12—C8	101.8 (3)
C5—C6—C1	120.5 (3)	C11—C12—H12A	111.4
C5—C6—H6	119.7	C8—C12—H12A	111.4
C1—C6—H6	119.7	C11—C12—H12B	111.4
N1—C7—C1	127.8 (3)	C8—C12—H12B	111.4
N1—C7—H7	116.1	H12A—C12—H12B	109.3
C1—C7—H7	116.1