Bis{2-[(2-cyano-phen-yl)imino-meth-yl]phenolato}copper(II).

In the title mononuclear copper(II) complex, [Cu(C(14)H(9)N(2)O)(2)], the Cu(II) atom, situated on an inversion centre, shows a slightly distorted square-planar geometry and is coordinated by the N and O atoms from two deprotonated symmetry-related Schiff base ligands. The Cu-N and Cu-O bond lengths are 2.009 (2) and 1.888 (2) Å, respectively. The dihedral angle between the cyano-phenyl rings and phenolate rings is 42.28 (13)°.

Related literature

For Schiff base complexes with copper(II) and nickel(II), see: Gong et al. (2008 ▶); Kitaura et al. (2004 ▶); Marganian et al. (1995 ▶). For bond-length data, see: Jian et al. (2004 ▶); Ünver (2002 ▶). For a related structure, see: Xia et al. (2008 ▶).

Experimental

Crystal data

[Cu(C14H9N2O)2]

M = 506.00

Monoclinic,

a = 9.698 (3) Å

b = 11.403 (3) Å

c = 10.889 (3) Å

β = 107.570 (11)°

V = 1148.0 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.99 mm−1

T = 293 (2) K

0.15 × 0.10 × 0.10 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.909, T max = 1.000 (expected range = 0.824–0.906)

11307 measured reflections

2629 independent reflections

1952 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.125

S = 1.09

2629 reflections

160 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803417X/gw2050sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803417X/gw2050Isup2.hkl

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

[Cu(C14H9N2O)2]	F000 = 518
Mr = 506.00	Dx = 1.464 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2373 reflections
a = 9.698 (3) Å	θ = 3.1–27.4º
b = 11.403 (3) Å	µ = 0.99 mm−1
c = 10.889 (3) Å	T = 293 (2) K
β = 107.570 (11)º	Block, red
V = 1148.0 (6) Å3	0.15 × 0.10 × 0.10 mm
Z = 2

Rigaku Mercury2 diffractometer	2629 independent reflections
Radiation source: fine-focus sealed tube	1952 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.057
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.1º
ω scans	h = −12→12
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −14→14
Tmin = 0.909, Tmax = 1.000	l = −14→14
11307 measured reflections

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0516P)2 + 0.2943P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2629 reflections	Δρmax = 0.26 e Å−3
160 parameters	Δρmin = −0.43 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	1.0000	0.5000	0.0000	0.03878 (18)
N1	0.9612 (2)	0.6674 (2)	0.0368 (2)	0.0383 (5)
O1	1.0810 (2)	0.46983 (18)	0.1778 (2)	0.0469 (5)
C8	0.8569 (3)	0.7359 (3)	−0.0563 (3)	0.0400 (6)
C1	1.1420 (3)	0.6686 (3)	0.2473 (3)	0.0416 (7)
C7	1.0377 (3)	0.7214 (3)	0.1397 (3)	0.0416 (7)
H7A	1.0234	0.8018	0.1439	0.050*
C9	0.7154 (3)	0.6925 (3)	−0.1043 (3)	0.0469 (7)
C2	1.1568 (3)	0.5450 (3)	0.2631 (3)	0.0403 (7)
C4	1.3310 (4)	0.5785 (3)	0.4717 (3)	0.0587 (9)
H4A	1.3938	0.5479	0.5471	0.070*
C6	1.2221 (3)	0.7432 (3)	0.3469 (3)	0.0535 (8)
H6A	1.2098	0.8239	0.3373	0.064*
C13	0.8922 (4)	0.8413 (3)	−0.1019 (3)	0.0507 (8)
H13A	0.9852	0.8715	−0.0698	0.061*
C14	0.6811 (3)	0.5801 (3)	−0.0602 (3)	0.0539 (8)
C10	0.6108 (4)	0.7564 (4)	−0.1967 (3)	0.0624 (10)
H10A	0.5162	0.7291	−0.2270	0.075*
C12	0.7880 (5)	0.9012 (3)	−0.1957 (4)	0.0670 (10)
H12A	0.8126	0.9711	−0.2280	0.080*
C5	1.3176 (4)	0.6996 (3)	0.4574 (3)	0.0601 (9)
H5A	1.3720	0.7496	0.5211	0.072*
C3	1.2547 (4)	0.5035 (3)	0.3782 (3)	0.0507 (8)
H3A	1.2678	0.4231	0.3909	0.061*
N2	0.6591 (4)	0.4905 (3)	−0.0242 (4)	0.0716 (9)
C11	0.6491 (5)	0.8599 (4)	−0.2422 (4)	0.0729 (12)
H11A	0.5805	0.9021	−0.3049	0.087*

	U11	U22	U33	U12	U13	U23
Cu1	0.0424 (3)	0.0348 (3)	0.0347 (3)	0.0037 (2)	0.0050 (2)	−0.0003 (2)
N1	0.0399 (13)	0.0373 (13)	0.0349 (12)	0.0036 (10)	0.0069 (10)	0.0010 (10)
O1	0.0581 (14)	0.0381 (12)	0.0378 (12)	0.0047 (9)	0.0046 (10)	−0.0004 (8)
C8	0.0428 (16)	0.0400 (16)	0.0340 (15)	0.0077 (12)	0.0066 (12)	−0.0006 (12)
C1	0.0385 (16)	0.0445 (17)	0.0373 (16)	0.0018 (12)	0.0044 (12)	−0.0004 (12)
C7	0.0445 (17)	0.0332 (15)	0.0433 (16)	0.0020 (12)	0.0074 (13)	−0.0001 (12)
C9	0.0429 (18)	0.0526 (19)	0.0407 (17)	0.0068 (14)	0.0059 (13)	−0.0004 (14)
C2	0.0407 (17)	0.0443 (16)	0.0349 (15)	0.0040 (13)	0.0098 (13)	0.0009 (12)
C4	0.050 (2)	0.073 (3)	0.0432 (19)	0.0075 (17)	−0.0005 (15)	0.0027 (16)
C6	0.058 (2)	0.0493 (19)	0.0458 (19)	−0.0028 (15)	0.0038 (15)	−0.0048 (14)
C13	0.057 (2)	0.0476 (18)	0.0479 (19)	0.0047 (15)	0.0162 (15)	0.0054 (14)
C14	0.0386 (18)	0.071 (2)	0.0456 (19)	−0.0032 (16)	0.0030 (14)	−0.0054 (17)
C10	0.046 (2)	0.081 (3)	0.050 (2)	0.0174 (18)	−0.0011 (16)	0.0000 (18)
C12	0.092 (3)	0.051 (2)	0.055 (2)	0.0172 (19)	0.018 (2)	0.0155 (16)
C5	0.061 (2)	0.065 (2)	0.0416 (19)	−0.0074 (17)	−0.0045 (16)	−0.0060 (16)
C3	0.056 (2)	0.0516 (19)	0.0402 (17)	0.0096 (15)	0.0080 (14)	0.0061 (14)
N2	0.064 (2)	0.067 (2)	0.077 (2)	−0.0158 (16)	0.0115 (17)	0.0050 (17)
C11	0.079 (3)	0.073 (3)	0.055 (2)	0.036 (2)	0.003 (2)	0.0149 (19)

Cu1—O1i	1.888 (2)	C4—C3	1.364 (4)
Cu1—O1	1.888 (2)	C4—C5	1.391 (5)
Cu1—N1i	2.009 (2)	C4—H4A	0.9300
Cu1—N1	2.009 (2)	C6—C5	1.371 (4)
N1—C7	1.298 (3)	C6—H6A	0.9300
N1—C8	1.429 (3)	C13—C12	1.381 (4)
O1—C2	1.313 (4)	C13—H13A	0.9300
C8—C13	1.382 (4)	C14—N2	1.137 (4)
C8—C9	1.403 (4)	C10—C11	1.374 (5)
C1—C2	1.421 (4)	C10—H10A	0.9300
C1—C6	1.413 (4)	C12—C11	1.372 (5)
C1—C7	1.429 (4)	C12—H12A	0.9300
C7—H7A	0.9300	C5—H5A	0.9300
C9—C10	1.398 (4)	C3—H3A	0.9300
C9—C14	1.443 (5)	C11—H11A	0.9300
C2—C3	1.407 (4)
O1i—Cu1—O1	180.00 (12)	C3—C4—C5	121.9 (3)
O1i—Cu1—N1i	90.78 (9)	C3—C4—H4A	119.1
O1—Cu1—N1i	89.22 (9)	C5—C4—H4A	119.1
O1i—Cu1—N1	89.22 (9)	C5—C6—C1	121.7 (3)
O1—Cu1—N1	90.78 (9)	C5—C6—H6A	119.2
N1i—Cu1—N1	180.00 (13)	C1—C6—H6A	119.2
C7—N1—C8	116.8 (2)	C8—C13—C12	119.4 (3)
C7—N1—Cu1	122.03 (19)	C8—C13—H13A	120.3
C8—N1—Cu1	120.84 (18)	C12—C13—H13A	120.3
C2—O1—Cu1	125.24 (19)	N2—C14—C9	177.6 (4)
C13—C8—C9	119.5 (3)	C11—C10—C9	119.4 (3)
C13—C8—N1	122.1 (3)	C11—C10—H10A	120.3
C9—C8—N1	118.4 (3)	C9—C10—H10A	120.3
C2—C1—C6	119.5 (3)	C11—C12—C13	121.3 (4)
C2—C1—C7	122.5 (3)	C11—C12—H12A	119.3
C6—C1—C7	117.7 (3)	C13—C12—H12A	119.3
N1—C7—C1	125.9 (3)	C6—C5—C4	118.3 (3)
N1—C7—H7A	117.1	C6—C5—H5A	120.9
C1—C7—H7A	117.1	C4—C5—H5A	120.9
C8—C9—C10	120.0 (3)	C4—C3—C2	121.5 (3)
C8—C9—C14	119.1 (3)	C4—C3—H3A	119.3
C10—C9—C14	120.8 (3)	C2—C3—H3A	119.3
O1—C2—C3	119.6 (3)	C12—C11—C10	120.3 (3)
O1—C2—C1	123.2 (3)	C12—C11—H11A	119.9
C3—C2—C1	117.2 (3)	C10—C11—H11A	119.9