Bis[4-chloro-2-(imino-meth-yl)phenolato]copper(II).

In the title mononuclear copper(II) complex, [Cu(C(7)H(5)ClNO)(2)], the Cu atom, situated on an inversion center, is four-coordinated, in a slightly distorted square-planar geometry, by the N- and O-donor atoms of two symmetry-related 4-chloro-2-(imino-meth-yl)phenolate Schiff base ligands.

Related literature

For the isotypic Ni(II) complex, see: Hong (2009 ▶). For bio-inorganic chemistry and the coordination chemistry of copper(II) complexes, see: Datta et al. (2008 ▶); Diallo et al. (2008 ▶); Khalaji et al. (2009 ▶).

Experimental

Crystal data

[Cu(C7H5ClNO)2]

M = 372.68

Monoclinic,

a = 15.775 (4) Å

b = 5.6949 (14) Å

c = 7.886 (2) Å

β = 93.932 (3)°

V = 706.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.93 mm−1

T = 298 K

0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.723, T max = 0.735

3835 measured reflections

1488 independent reflections

1025 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.139

S = 1.01

1488 reflections

97 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.57 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/S1600536809007624/su2100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007624/su2100Isup2.hkl

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

[Cu(C7H5ClNO)2]	F(000) = 374
Mr = 372.68	Dx = 1.751 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.775 (4) Å	Cell parameters from 811 reflections
b = 5.6949 (14) Å	θ = 2.5–24.3°
c = 7.886 (2) Å	µ = 1.93 mm−1
β = 93.932 (3)°	T = 298 K
V = 706.8 (3) Å3	Cut from needle, blue
Z = 2	0.18 × 0.17 × 0.17 mm

Bruker SMART CCD area-detector diffractometer	1488 independent reflections
Radiation source: fine-focus sealed tube	1025 reflections with I > 2σ(I)
graphite	Rint = 0.038
ω scans	θmax = 26.7°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.723, Tmax = 0.735	k = −7→4
3835 measured reflections	l = −9→9

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0757P)2 + 0.0803P] where P = (Fo2 + 2Fc2)/3
1488 reflections	(Δ/σ)max < 0.001
97 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.57 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	0.5000	1.0000	1.0000	0.0394 (3)
Cl1	0.93518 (8)	0.8488 (3)	0.8060 (2)	0.0767 (5)
N1	0.5411 (2)	0.7404 (6)	0.8909 (4)	0.0407 (8)
H1	0.5043	0.6336	0.8631	0.049*
O1	0.60283 (17)	1.1520 (5)	1.0157 (4)	0.0418 (7)
C1	0.6875 (3)	0.8577 (7)	0.8857 (5)	0.0361 (9)
C2	0.6766 (3)	1.0747 (7)	0.9685 (5)	0.0369 (9)
C3	0.7494 (3)	1.2131 (8)	1.0047 (5)	0.0446 (11)
H3	0.7444	1.3543	1.0624	0.053*
C4	0.8280 (3)	1.1444 (8)	0.9568 (6)	0.0506 (12)
H4	0.8751	1.2397	0.9817	0.061*
C5	0.8372 (3)	0.9355 (8)	0.8721 (6)	0.0468 (11)
C6	0.7682 (3)	0.7904 (8)	0.8369 (6)	0.0460 (11)
H6	0.7749	0.6485	0.7811	0.055*
C7	0.6171 (3)	0.6979 (7)	0.8509 (5)	0.0411 (10)
H7	0.6274	0.5568	0.7967	0.049*

	U11	U22	U33	U12	U13	U23
Cu1	0.0443 (5)	0.0320 (4)	0.0413 (5)	−0.0014 (3)	−0.0013 (3)	−0.0036 (3)
Cl1	0.0436 (7)	0.0892 (11)	0.0988 (12)	0.0013 (7)	0.0152 (7)	−0.0162 (9)
N1	0.041 (2)	0.0338 (19)	0.047 (2)	−0.0048 (15)	−0.0007 (16)	−0.0067 (15)
O1	0.0398 (17)	0.0346 (17)	0.0509 (18)	−0.0019 (12)	0.0033 (13)	−0.0081 (13)
C1	0.041 (2)	0.031 (2)	0.036 (2)	−0.0007 (17)	−0.0005 (17)	0.0020 (17)
C2	0.046 (3)	0.031 (2)	0.033 (2)	−0.0010 (18)	−0.0024 (18)	−0.0008 (16)
C3	0.051 (3)	0.034 (2)	0.048 (3)	−0.0038 (19)	−0.003 (2)	−0.0040 (18)
C4	0.042 (3)	0.052 (3)	0.057 (3)	−0.008 (2)	−0.001 (2)	0.002 (2)
C5	0.037 (2)	0.052 (3)	0.051 (3)	0.003 (2)	0.004 (2)	0.001 (2)
C6	0.051 (3)	0.040 (3)	0.048 (3)	0.006 (2)	0.004 (2)	0.0001 (19)
C7	0.050 (3)	0.030 (2)	0.042 (2)	0.0008 (18)	−0.0004 (19)	−0.0048 (18)

Cu1—O1i	1.835 (3)	C1—C7	1.447 (6)
Cu1—O1	1.835 (3)	C2—C3	1.406 (6)
Cu1—N1i	1.850 (3)	C3—C4	1.378 (6)
Cu1—N1	1.850 (3)	C3—H3	0.9300
Cl1—C5	1.736 (5)	C4—C5	1.377 (7)
N1—C7	1.282 (5)	C4—H4	0.9300
N1—H1	0.8600	C5—C6	1.380 (6)
O1—C2	1.321 (5)	C6—H6	0.9300
C1—C6	1.408 (6)	C7—H7	0.9300
C1—C2	1.413 (6)
O1i—Cu1—O1	180.00 (8)	C4—C3—C2	121.6 (4)
O1i—Cu1—N1i	94.10 (14)	C4—C3—H3	119.2
O1—Cu1—N1i	85.90 (14)	C2—C3—H3	119.2
O1i—Cu1—N1	85.90 (14)	C5—C4—C3	120.3 (4)
O1—Cu1—N1	94.10 (14)	C5—C4—H4	119.8
N1i—Cu1—N1	180.000 (1)	C3—C4—H4	119.8
C7—N1—Cu1	128.9 (3)	C4—C5—C6	120.5 (4)
C7—N1—H1	115.5	C4—C5—Cl1	121.1 (4)
Cu1—N1—H1	115.5	C6—C5—Cl1	118.4 (4)
C2—O1—Cu1	128.0 (3)	C5—C6—C1	119.9 (4)
C6—C1—C2	120.3 (4)	C5—C6—H6	120.1
C6—C1—C7	118.3 (4)	C1—C6—H6	120.1
C2—C1—C7	121.4 (4)	N1—C7—C1	123.5 (4)
O1—C2—C3	118.6 (4)	N1—C7—H7	118.2
O1—C2—C1	124.0 (4)	C1—C7—H7	118.2
C3—C2—C1	117.4 (4)