Bis[2-(cyclo-hexyl-imino-meth-yl)-5-methoxy-phenolato]copper(II).

In the title centrosymmetric mononuclear complex, [Cu(C(14)H(18)NO(2))(2)], the Cu(II) ion, lying on an inversion centre, is four-coordinated by two imine N and two phenolate O atoms from two Schiff base ligands, forming a slightly distorted square-planar geometry.

Related literature

For general background to copper complexes, see: Collinson & Fenton (1996 ▶); Hossain et al. (1996 ▶); Tarafder et al. (2002 ▶); Musie et al. (2003 ▶); García-Raso et al. (2003 ▶); Reddy et al. (2000 ▶); Ray et al. (2003 ▶); Arnold et al. (2003 ▶); Raptopoulou et al. (1998 ▶). For related structures, see: Miao (2005 ▶, 2006 ▶); Wang (2007 ▶); Zhang (2004 ▶); Akitsu & Einaga (2004 ▶); Bluhm et al. (2003 ▶); Castillo et al. (2003 ▶); Lacroix et al. (2004 ▶).

Experimental

Crystal data

[Cu(C14H18NO2)2]

M = 528.13

Monoclinic,

a = 6.4557 (10) Å

b = 11.5170 (17) Å

c = 17.074 (3) Å

β = 99.138 (2)°

V = 1253.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.91 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.818, T max = 0.839

6860 measured reflections

2727 independent reflections

2232 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.080

S = 1.04

2727 reflections

161 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.25 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/S1600536809051629/ci2979sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051629/ci2979Isup2.hkl

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

[Cu(C14H18NO2)2]	F(000) = 558
Mr = 528.13	Dx = 1.399 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2706 reflections
a = 6.4557 (10) Å	θ = 2.4–28.7°
b = 11.5170 (17) Å	µ = 0.91 mm−1
c = 17.074 (3) Å	T = 298 K
β = 99.138 (2)°	Block, blue
V = 1253.4 (3) Å3	0.23 × 0.20 × 0.20 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2727 independent reflections
Radiation source: fine-focus sealed tube	2232 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→8
Tmin = 0.818, Tmax = 0.839	k = −14→14
6860 measured reflections	l = −17→21

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0393P)2 + 0.3443P] where P = (Fo2 + 2Fc2)/3
2727 reflections	(Δ/σ)max = 0.001
161 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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	0.0000	0.0000	0.0000	0.02741 (11)
N1	0.2825 (2)	−0.05099 (13)	0.05759 (8)	0.0279 (3)
O1	−0.02292 (18)	0.11030 (12)	0.08083 (8)	0.0369 (3)
O2	0.2183 (2)	0.44832 (13)	0.22866 (8)	0.0435 (3)
C1	0.3444 (3)	0.13149 (15)	0.12935 (10)	0.0293 (4)
C2	0.1333 (3)	0.17066 (15)	0.11880 (10)	0.0290 (4)
C3	0.0893 (3)	0.27716 (16)	0.15350 (11)	0.0324 (4)
H3	−0.0488	0.3025	0.1492	0.039*
C4	0.2490 (3)	0.34426 (15)	0.19372 (10)	0.0321 (4)
C5	0.4579 (3)	0.30770 (17)	0.20160 (12)	0.0377 (4)
H5	0.5654	0.3543	0.2271	0.045*
C6	0.5013 (3)	0.20248 (16)	0.17120 (11)	0.0350 (4)
H6	0.6396	0.1769	0.1784	0.042*
C7	0.4013 (3)	0.01873 (15)	0.10362 (11)	0.0314 (4)
H7	0.5373	−0.0064	0.1220	0.038*
C8	0.3570 (3)	−0.17037 (15)	0.04404 (11)	0.0292 (4)
H8	0.3409	−0.1818	−0.0135	0.035*
C9	0.5849 (3)	−0.19822 (16)	0.07803 (12)	0.0344 (4)
H9A	0.6775	−0.1459	0.0555	0.041*
H9B	0.6075	−0.1871	0.1351	0.041*
C10	0.6355 (3)	−0.32350 (17)	0.05889 (14)	0.0425 (5)
H10A	0.7792	−0.3409	0.0820	0.051*
H10B	0.6229	−0.3327	0.0019	0.051*
C11	0.4882 (3)	−0.40877 (17)	0.09089 (14)	0.0448 (5)
H11A	0.5208	−0.4873	0.0763	0.054*
H11B	0.5082	−0.4041	0.1483	0.054*
C12	0.2621 (3)	−0.38098 (17)	0.05739 (14)	0.0455 (5)
H12A	0.1699	−0.4333	0.0801	0.055*
H12B	0.2392	−0.3927	0.0004	0.055*
C13	0.2090 (3)	−0.25579 (16)	0.07562 (13)	0.0389 (4)
H13A	0.2194	−0.2461	0.1325	0.047*
H13B	0.0656	−0.2391	0.0517	0.047*
C14	0.0085 (4)	0.48443 (19)	0.23134 (17)	0.0591 (7)
H14A	−0.0676	0.4892	0.1784	0.089*
H14B	0.0100	0.5592	0.2562	0.089*
H14C	−0.0583	0.4292	0.2612	0.089*

	U11	U22	U33	U12	U13	U23
Cu1	0.02394 (16)	0.02709 (17)	0.02975 (17)	0.00081 (12)	−0.00020 (11)	−0.00354 (12)
N1	0.0262 (7)	0.0262 (7)	0.0306 (8)	0.0021 (6)	0.0025 (6)	0.0001 (6)
O1	0.0262 (6)	0.0415 (7)	0.0409 (7)	0.0005 (5)	−0.0011 (5)	−0.0141 (6)
O2	0.0426 (8)	0.0368 (8)	0.0501 (8)	−0.0028 (6)	0.0043 (6)	−0.0145 (7)
C1	0.0277 (9)	0.0301 (9)	0.0289 (9)	−0.0006 (7)	0.0011 (7)	−0.0003 (7)
C2	0.0281 (9)	0.0321 (9)	0.0260 (8)	−0.0018 (7)	0.0018 (7)	0.0001 (7)
C3	0.0274 (9)	0.0356 (10)	0.0335 (9)	0.0023 (7)	0.0024 (7)	−0.0039 (8)
C4	0.0396 (10)	0.0278 (9)	0.0287 (9)	−0.0018 (8)	0.0045 (8)	−0.0017 (7)
C5	0.0327 (10)	0.0374 (11)	0.0412 (11)	−0.0090 (8)	−0.0001 (8)	−0.0053 (9)
C6	0.0269 (9)	0.0371 (10)	0.0393 (10)	−0.0012 (8)	0.0005 (7)	−0.0015 (8)
C7	0.0251 (9)	0.0355 (10)	0.0325 (9)	0.0015 (7)	0.0014 (7)	0.0025 (7)
C8	0.0275 (9)	0.0278 (9)	0.0322 (9)	0.0027 (7)	0.0040 (7)	0.0009 (7)
C9	0.0280 (9)	0.0311 (10)	0.0439 (11)	0.0013 (7)	0.0047 (8)	0.0026 (8)
C10	0.0333 (10)	0.0361 (11)	0.0592 (13)	0.0076 (8)	0.0107 (9)	0.0050 (9)
C11	0.0474 (12)	0.0291 (10)	0.0588 (13)	0.0049 (9)	0.0115 (10)	0.0069 (9)
C12	0.0433 (11)	0.0317 (10)	0.0634 (14)	−0.0039 (9)	0.0143 (10)	0.0029 (10)
C13	0.0297 (9)	0.0347 (10)	0.0537 (12)	−0.0009 (8)	0.0111 (8)	0.0024 (9)
C14	0.0502 (13)	0.0549 (15)	0.0724 (17)	0.0048 (11)	0.0106 (12)	−0.0306 (12)

Cu1—O1i	1.8987 (12)	C8—C9	1.527 (2)
Cu1—O1	1.8987 (12)	C8—C13	1.528 (2)
Cu1—N1i	2.0169 (14)	C8—H8	0.98
Cu1—N1	2.0169 (14)	C9—C10	1.526 (3)
N1—C7	1.288 (2)	C9—H9A	0.97
N1—C8	1.487 (2)	C9—H9B	0.97
O1—C2	1.309 (2)	C10—C11	1.527 (3)
O2—C4	1.367 (2)	C10—H10A	0.97
O2—C14	1.424 (3)	C10—H10B	0.97
C1—C6	1.406 (2)	C11—C12	1.515 (3)
C1—C2	1.420 (2)	C11—H11A	0.97
C1—C7	1.437 (2)	C11—H11B	0.97
C2—C3	1.411 (2)	C12—C13	1.525 (3)
C3—C4	1.381 (2)	C12—H12A	0.97
C3—H3	0.93	C12—H12B	0.97
C4—C5	1.399 (3)	C13—H13A	0.97
C5—C6	1.365 (3)	C13—H13B	0.97
C5—H5	0.93	C14—H14A	0.96
C6—H6	0.93	C14—H14B	0.96
C7—H7	0.93	C14—H14C	0.96
O1i—Cu1—O1	180.00 (10)	C13—C8—H8	107.1
O1i—Cu1—N1i	90.53 (5)	C10—C9—C8	110.06 (15)
O1—Cu1—N1i	89.47 (5)	C10—C9—H9A	109.6
O1i—Cu1—N1	89.47 (5)	C8—C9—H9A	109.6
O1—Cu1—N1	90.53 (5)	C10—C9—H9B	109.6
N1i—Cu1—N1	180.00 (11)	C8—C9—H9B	109.6
C7—N1—C8	119.69 (15)	H9A—C9—H9B	108.2
C7—N1—Cu1	121.37 (12)	C9—C10—C11	111.40 (16)
C8—N1—Cu1	118.90 (11)	C9—C10—H10A	109.3
C2—O1—Cu1	124.93 (11)	C11—C10—H10A	109.3
C4—O2—C14	118.32 (15)	C9—C10—H10B	109.3
C6—C1—C2	118.65 (16)	C11—C10—H10B	109.3
C6—C1—C7	118.84 (16)	H10A—C10—H10B	108.0
C2—C1—C7	122.36 (16)	C12—C11—C10	110.27 (17)
O1—C2—C3	118.64 (15)	C12—C11—H11A	109.6
O1—C2—C1	122.87 (16)	C10—C11—H11A	109.6
C3—C2—C1	118.44 (16)	C12—C11—H11B	109.6
C4—C3—C2	120.76 (16)	C10—C11—H11B	109.6
C4—C3—H3	119.6	H11A—C11—H11B	108.1
C2—C3—H3	119.6	C11—C12—C13	110.90 (17)
O2—C4—C3	124.00 (17)	C11—C12—H12A	109.5
O2—C4—C5	115.23 (16)	C13—C12—H12A	109.5
C3—C4—C5	120.77 (17)	C11—C12—H12B	109.5
C6—C5—C4	118.93 (17)	C13—C12—H12B	109.5
C6—C5—H5	120.5	H12A—C12—H12B	108.0
C4—C5—H5	120.5	C12—C13—C8	111.31 (15)
C5—C6—C1	122.33 (17)	C12—C13—H13A	109.4
C5—C6—H6	118.8	C8—C13—H13A	109.4
C1—C6—H6	118.8	C12—C13—H13B	109.4
N1—C7—C1	126.40 (17)	C8—C13—H13B	109.4
N1—C7—H7	116.8	H13A—C13—H13B	108.0
C1—C7—H7	116.8	O2—C14—H14A	109.5
N1—C8—C9	116.81 (14)	O2—C14—H14B	109.5
N1—C8—C13	107.74 (13)	H14A—C14—H14B	109.5
C9—C8—C13	110.43 (15)	O2—C14—H14C	109.5
N1—C8—H8	107.1	H14A—C14—H14C	109.5
C9—C8—H8	107.1	H14B—C14—H14C	109.5