[(1S,2S)-2-(1-{[2-(2-Oxidobenzyl-idene-amino)-cyclo-hex-yl]imino}-eth-yl)phenolato-κO,N,N',O']copper(II).

In the title compound, [Cu(C(21)H(22)N(2)O(2))], the cyclo-hexyl ring adopts a chair conformation with the two imine groups linked at equatorial positions. The Cu(II) ion is coordinated by two N atoms and two O atoms from the bis-Schiff base ligand in a slightly distorted square-planar geometry. The dihedral angle between the two benzene rings is 45.89 (9)°. The crystal structure is devoid of any classical hydrogen bonds. However, inter-molecular C-H⋯O inter-actions are present and stabilize the structure.

Related literature

For the crystal structures of a similar symmetrical compound see: Yao et al. (1997 ▶). For metal complexes of unsymmetrical bis-Schiff bases, see: Lashanizadegan & Boghaei (2002 ▶); Rabie et al. (2008 ▶).

Experimental

Crystal data

[Cu(C21H22N2O2)]

M = 397.95

Monoclinic,

a = 9.6699 (3) Å

b = 7.7324 (2) Å

c = 12.1847 (4) Å

β = 111.649 (2)°

V = 846.80 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.31 mm−1

T = 100 K

0.20 × 0.10 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.780, T max = 0.962

9232 measured reflections

4573 independent reflections

3542 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.091

S = 0.97

4573 reflections

236 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.37 e Å−3

Absolute structure: Flack (1983 ▶), 2036 Friedel pairs

Flack parameter: 0.050 (15)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022889/pv2290sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022889/pv2290Isup2.hkl

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

[Cu(C21H22N2O2)]	F(000) = 414
Mr = 397.95	Dx = 1.561 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1422 reflections
a = 9.6699 (3) Å	θ = 3.2–23.5°
b = 7.7324 (2) Å	µ = 1.31 mm−1
c = 12.1847 (4) Å	T = 100 K
β = 111.649 (2)°	Block, green
V = 846.80 (4) Å3	0.20 × 0.10 × 0.03 mm
Z = 2

Bruker APEXII CCD diffractometer	4573 independent reflections
Radiation source: fine-focus sealed tube	3542 reflections with I > 2σ(I)
graphite	Rint = 0.053
φ and ω scans	θmax = 29.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.780, Tmax = 0.962	k = −10→10
9232 measured reflections	l = −16→16

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0281P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
4573 reflections	Δρmax = 0.39 e Å−3
236 parameters	Δρmin = −0.37 e Å−3
1 restraint	Absolute structure: Flack (1983), 2036 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.050 (15)

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	0.09681 (4)	0.25280 (6)	0.05446 (3)	0.01389 (10)
O1	0.1603 (3)	0.2029 (3)	−0.0696 (2)	0.0199 (7)
O2	0.2941 (3)	0.3130 (3)	0.1540 (2)	0.0179 (6)
N1	−0.1155 (3)	0.2570 (8)	−0.0484 (2)	0.0158 (5)
N2	0.0262 (3)	0.2546 (7)	0.1826 (2)	0.0148 (5)
C1	0.0826 (4)	0.2231 (4)	−0.1822 (3)	0.0146 (8)
C2	0.1533 (4)	0.1917 (5)	−0.2626 (4)	0.0210 (9)
H2	0.2528	0.1501	−0.2330	0.025*
C3	0.0850 (4)	0.2184 (5)	−0.3815 (3)	0.0239 (10)
H3	0.1355	0.1914	−0.4331	0.029*
C4	−0.0588 (4)	0.2855 (5)	−0.4267 (3)	0.0250 (11)
H4	−0.1056	0.3099	−0.5085	0.030*
C5	−0.1319 (4)	0.3158 (5)	−0.3509 (3)	0.0206 (8)
H5	−0.2306	0.3595	−0.3825	0.025*
C6	−0.0671 (4)	0.2850 (4)	−0.2290 (3)	0.0142 (9)
C7	−0.1594 (4)	0.3112 (4)	−0.1567 (3)	0.0143 (7)
C8	−0.3037 (4)	0.4067 (5)	−0.2152 (4)	0.0250 (10)
H8A	−0.3788	0.3272	−0.2664	0.038*
H8B	−0.2886	0.5021	−0.2625	0.038*
H8C	−0.3378	0.4531	−0.1546	0.038*
C9	−0.2129 (3)	0.2699 (6)	0.0225 (3)	0.0135 (7)
H9	−0.2298	0.3943	0.0363	0.016*
C10	−0.3627 (4)	0.1763 (5)	−0.0305 (3)	0.0185 (8)
H10A	−0.4222	0.2286	−0.1078	0.022*
H10B	−0.3457	0.0531	−0.0438	0.022*
C11	−0.4481 (4)	0.1894 (5)	0.0520 (3)	0.0198 (8)
H11A	−0.4679	0.3125	0.0631	0.024*
H11B	−0.5450	0.1296	0.0162	0.024*
C12	−0.3605 (4)	0.1086 (5)	0.1712 (4)	0.0223 (9)
H12A	−0.3504	−0.0172	0.1611	0.027*
H12B	−0.4156	0.1250	0.2247	0.027*
C13	−0.2067 (4)	0.1891 (5)	0.2264 (3)	0.0189 (8)
H13A	−0.1487	0.1261	0.2998	0.023*
H13B	−0.2163	0.3110	0.2474	0.023*
C14	−0.1252 (4)	0.1816 (5)	0.1409 (3)	0.0164 (8)
H14	−0.1162	0.0566	0.1234	0.020*
C15	0.0955 (4)	0.3110 (4)	0.2870 (3)	0.0174 (8)
H15	0.0441	0.3094	0.3401	0.021*
C16	0.2456 (4)	0.3770 (4)	0.3309 (3)	0.0155 (8)
C17	0.3008 (4)	0.4505 (5)	0.4447 (3)	0.0206 (9)
H17	0.2403	0.4492	0.4908	0.025*
C18	0.4390 (4)	0.5235 (5)	0.4905 (4)	0.0221 (9)
H18	0.4736	0.5739	0.5670	0.026*
C19	0.5288 (4)	0.5227 (5)	0.4230 (4)	0.0222 (9)
H19	0.6250	0.5734	0.4539	0.027*
C20	0.4793 (4)	0.4495 (5)	0.3123 (3)	0.0187 (8)
H20	0.5437	0.4474	0.2694	0.022*
C21	0.3353 (4)	0.3770 (5)	0.2605 (3)	0.0174 (8)

	U11	U22	U33	U12	U13	U23
Cu1	0.01095 (17)	0.01506 (18)	0.0154 (2)	0.0002 (3)	0.00449 (14)	0.0004 (3)
O1	0.0160 (13)	0.0234 (17)	0.0211 (15)	0.0011 (10)	0.0077 (12)	−0.0015 (10)
O2	0.0134 (12)	0.0244 (14)	0.0159 (14)	−0.0023 (11)	0.0054 (11)	−0.0004 (10)
N1	0.0127 (13)	0.0195 (13)	0.0160 (13)	0.000 (2)	0.0061 (11)	−0.002 (2)
N2	0.0099 (12)	0.0176 (12)	0.0156 (13)	0.002 (2)	0.0033 (10)	0.000 (2)
C1	0.0217 (17)	0.004 (2)	0.0186 (18)	−0.0023 (14)	0.0084 (15)	−0.0016 (13)
C2	0.0205 (19)	0.0154 (18)	0.030 (2)	0.0004 (15)	0.0132 (18)	−0.0034 (16)
C3	0.033 (2)	0.020 (3)	0.025 (2)	−0.0004 (17)	0.0173 (18)	−0.0067 (16)
C4	0.033 (2)	0.024 (3)	0.0184 (19)	−0.0016 (18)	0.0100 (17)	−0.0004 (16)
C5	0.0200 (19)	0.0220 (18)	0.019 (2)	−0.0013 (16)	0.0060 (16)	0.0010 (15)
C6	0.0173 (17)	0.007 (2)	0.0190 (18)	−0.0004 (14)	0.0078 (14)	−0.0013 (13)
C7	0.0124 (17)	0.0111 (16)	0.0185 (19)	−0.0032 (13)	0.0045 (15)	−0.0039 (14)
C8	0.019 (2)	0.028 (2)	0.024 (2)	−0.0011 (18)	0.0031 (18)	−0.0012 (17)
C9	0.0119 (14)	0.0145 (19)	0.0157 (16)	0.0038 (18)	0.0071 (12)	0.0025 (18)
C10	0.0129 (18)	0.0211 (19)	0.021 (2)	−0.0027 (16)	0.0060 (16)	−0.0062 (16)
C11	0.0145 (18)	0.0249 (19)	0.021 (2)	−0.0025 (15)	0.0072 (17)	−0.0032 (15)
C12	0.017 (2)	0.021 (2)	0.032 (3)	−0.0038 (17)	0.0125 (19)	0.0007 (17)
C13	0.0188 (19)	0.0209 (18)	0.019 (2)	0.0016 (15)	0.0094 (16)	0.0028 (15)
C14	0.0138 (18)	0.0137 (17)	0.022 (2)	0.0013 (15)	0.0071 (16)	0.0000 (15)
C15	0.0136 (18)	0.0157 (18)	0.023 (2)	0.0034 (14)	0.0070 (16)	0.0025 (15)
C16	0.0151 (19)	0.0120 (17)	0.016 (2)	−0.0011 (15)	0.0023 (15)	0.0047 (14)
C17	0.019 (2)	0.0207 (19)	0.018 (2)	0.0039 (16)	0.0023 (17)	0.0016 (16)
C18	0.021 (2)	0.021 (2)	0.019 (2)	−0.0014 (17)	0.0010 (17)	−0.0038 (17)
C19	0.013 (2)	0.017 (2)	0.028 (2)	−0.0020 (16)	−0.0015 (17)	0.0030 (17)
C20	0.0131 (19)	0.0179 (19)	0.024 (2)	0.0001 (15)	0.0049 (17)	0.0045 (16)
C21	0.0160 (19)	0.0141 (18)	0.020 (2)	−0.0014 (15)	0.0049 (16)	0.0050 (15)

Cu1—O1	1.870 (2)	C9—H9	1.0000
Cu1—O2	1.903 (2)	C10—C11	1.522 (5)
Cu1—N2	1.921 (2)	C10—H10A	0.9900
Cu1—N1	1.972 (3)	C10—H10B	0.9900
O1—C1	1.307 (4)	C11—C12	1.519 (5)
O2—C21	1.306 (4)	C11—H11A	0.9900
N1—C7	1.298 (5)	C11—H11B	0.9900
N1—C9	1.498 (4)	C12—C13	1.521 (5)
N2—C15	1.277 (4)	C12—H12A	0.9900
N2—C14	1.474 (4)	C12—H12B	0.9900
C1—C2	1.407 (5)	C13—C14	1.522 (5)
C1—C6	1.429 (5)	C13—H13A	0.9900
C2—C3	1.368 (5)	C13—H13B	0.9900
C2—H2	0.9500	C14—H14	1.0000
C3—C4	1.394 (5)	C15—C16	1.443 (5)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.374 (5)	C16—C17	1.409 (5)
C4—H4	0.9500	C16—C21	1.427 (5)
C5—C6	1.403 (5)	C17—C18	1.366 (5)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.481 (5)	C18—C19	1.400 (6)
C7—C8	1.506 (5)	C18—H18	0.9500
C8—H8A	0.9800	C19—C20	1.376 (5)
C8—H8B	0.9800	C19—H19	0.9500
C8—H8C	0.9800	C20—C21	1.415 (5)
C9—C10	1.533 (5)	C20—H20	0.9500
C9—C14	1.538 (5)
O1—Cu1—O2	90.86 (11)	C9—C10—H10A	109.6
O1—Cu1—N2	168.46 (17)	C11—C10—H10B	109.6
O2—Cu1—N2	93.06 (11)	C9—C10—H10B	109.6
O1—Cu1—N1	93.73 (11)	H10A—C10—H10B	108.1
O2—Cu1—N1	164.81 (18)	C12—C11—C10	111.0 (3)
N2—Cu1—N1	85.27 (10)	C12—C11—H11A	109.4
C1—O1—Cu1	126.2 (2)	C10—C11—H11A	109.4
C21—O2—Cu1	126.4 (2)	C12—C11—H11B	109.4
C7—N1—C9	121.7 (3)	C10—C11—H11B	109.4
C7—N1—Cu1	121.6 (2)	H11A—C11—H11B	108.0
C9—N1—Cu1	111.31 (19)	C11—C12—C13	111.4 (3)
C15—N2—C14	124.3 (3)	C11—C12—H12A	109.4
C15—N2—Cu1	126.9 (3)	C13—C12—H12A	109.4
C14—N2—Cu1	108.9 (2)	C11—C12—H12B	109.4
O1—C1—C2	118.1 (3)	C13—C12—H12B	109.4
O1—C1—C6	124.3 (3)	H12A—C12—H12B	108.0
C2—C1—C6	117.4 (3)	C12—C13—C14	110.5 (3)
C3—C2—C1	122.9 (4)	C12—C13—H13A	109.6
C3—C2—H2	118.6	C14—C13—H13A	109.6
C1—C2—H2	118.6	C12—C13—H13B	109.6
C2—C3—C4	119.7 (3)	C14—C13—H13B	109.6
C2—C3—H3	120.1	H13A—C13—H13B	108.1
C4—C3—H3	120.1	N2—C14—C13	116.7 (3)
C5—C4—C3	118.9 (4)	N2—C14—C9	106.7 (3)
C5—C4—H4	120.5	C13—C14—C9	112.3 (3)
C3—C4—H4	120.5	N2—C14—H14	106.9
C4—C5—C6	122.9 (4)	C13—C14—H14	106.9
C4—C5—H5	118.5	C9—C14—H14	106.9
C6—C5—H5	118.5	N2—C15—C16	125.2 (3)
C5—C6—C1	118.0 (3)	N2—C15—H15	117.4
C5—C6—C7	118.4 (3)	C16—C15—H15	117.4
C1—C6—C7	123.5 (3)	C17—C16—C21	119.9 (3)
N1—C7—C6	121.2 (3)	C17—C16—C15	118.1 (4)
N1—C7—C8	122.5 (3)	C21—C16—C15	122.0 (3)
C6—C7—C8	116.3 (3)	C18—C17—C16	121.9 (4)
C7—C8—H8A	109.5	C18—C17—H17	119.1
C7—C8—H8B	109.5	C16—C17—H17	119.1
H8A—C8—H8B	109.5	C17—C18—C19	118.9 (4)
C7—C8—H8C	109.5	C17—C18—H18	120.6
H8A—C8—H8C	109.5	C19—C18—H18	120.6
H8B—C8—H8C	109.5	C20—C19—C18	120.7 (4)
N1—C9—C10	115.0 (3)	C20—C19—H19	119.6
N1—C9—C14	105.4 (3)	C18—C19—H19	119.6
C10—C9—C14	107.1 (3)	C19—C20—C21	122.0 (4)
N1—C9—H9	109.7	C19—C20—H20	119.0
C10—C9—H9	109.7	C21—C20—H20	119.0
C14—C9—H9	109.7	O2—C21—C20	118.9 (4)
C11—C10—C9	110.4 (3)	O2—C21—C16	124.5 (3)
C11—C10—H10A	109.6	C20—C21—C16	116.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1i	1.00	2.47	3.403 (6)	155
C10—H10B···O2ii	0.99	2.45	3.366 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1i	1.00	2.47	3.403 (6)	155
C10—H10B⋯O2ii	0.99	2.45	3.366 (4)	154

Symmetry codes: (i) ; (ii) .