Bis{(E)-2-[(2-chloro-3-pyrid-yl)imino-meth-yl]-6-meth-oxy-phenolato-κN,O}copper(II).

In the title mononuclear copper(II) complex, [Cu(C(13)H(10)ClN(2)O(2))(2)], the Cu(II) ion, lying on an inversion center, is four-coordinated in a trans-CuN(2)O(2) square-planar geometry by two phenolate O and two imino N atoms from two symmetry-related N,O-bidentate Schiff base ligands. The shortest Cu⋯Cu distance is 7.5743 (9) Å. However, there are weak intra-molecular electrostatic inter-actions between the Cu atom and the Cl atom of the ligand, with a Cu⋯Cl distance of 3.3845 (9) Å.

Related literature

For the synthesis and related crystal strcutures, see: Dong et al. (2009 ▶, 2010 ▶); Ding et al. (2009 ▶).

Experimental

Crystal data

[Cu(C13H10ClN2O2)2]

M = 586.90

Monoclinic,

a = 21.242 (2) Å

b = 7.5743 (9) Å

c = 16.141 (2) Å

β = 97.652 (1)°

V = 2573.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.10 mm−1

T = 298 K

0.18 × 0.16 × 0.11 mm

Data collection

Siemens SMART 1000 CCE diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.827, T max = 0.889

6295 measured reflections

2262 independent reflections

1651 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.075

S = 1.01

2262 reflections

170 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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/S1600536810052414/om2379sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052414/om2379Isup2.hkl

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

[Cu(C13H10ClN2O2)2]	F(000) = 1196
Mr = 586.90	Dx = 1.515 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1824 reflections
a = 21.242 (2) Å	θ = 2.9–25.2°
b = 7.5743 (9) Å	µ = 1.10 mm−1
c = 16.141 (2) Å	T = 298 K
β = 97.652 (1)°	Block, brown
V = 2573.9 (5) Å3	0.18 × 0.16 × 0.11 mm
Z = 4

Bruker SMART 1000 diffractometer	2262 independent reflections
Radiation source: fine-focus sealed tube	1651 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→25
Tmin = 0.827, Tmax = 0.889	k = −8→8
6295 measured reflections	l = −19→17

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0306P)2] where P = (Fo2 + 2Fc2)/3
2262 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.29 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	0.5000	0.0000	0.04162 (16)
Cl1	0.41342 (4)	0.44977 (10)	0.15993 (6)	0.0749 (3)
N1	0.53184 (10)	0.3389 (3)	0.09230 (13)	0.0415 (5)
N2	0.40093 (12)	0.1120 (3)	0.17745 (16)	0.0590 (7)
O1	0.56672 (8)	0.6625 (2)	0.03158 (12)	0.0494 (5)
O2	0.65231 (10)	0.9115 (3)	0.03223 (14)	0.0662 (6)
C1	0.58981 (13)	0.3453 (4)	0.13165 (17)	0.0452 (7)
H1	0.6021	0.2534	0.1685	0.054*
C2	0.63603 (12)	0.4787 (4)	0.12382 (16)	0.0442 (7)
C3	0.62132 (12)	0.6322 (4)	0.07655 (16)	0.0426 (7)
C4	0.67016 (13)	0.7650 (4)	0.07845 (18)	0.0495 (7)
C5	0.72880 (14)	0.7374 (4)	0.12438 (19)	0.0586 (8)
H5	0.7603	0.8228	0.1244	0.070*
C6	0.74167 (15)	0.5833 (4)	0.1708 (2)	0.0642 (9)
H6	0.7815	0.5668	0.2015	0.077*
C7	0.69649 (14)	0.4579 (4)	0.17153 (18)	0.0572 (8)
H7	0.7052	0.3568	0.2037	0.069*
C8	0.69847 (17)	1.0482 (4)	0.0302 (2)	0.0785 (11)
H8A	0.7120	1.0891	0.0860	0.118*
H8B	0.6801	1.1444	−0.0034	0.118*
H8C	0.7344	1.0028	0.0066	0.118*
C9	0.43771 (13)	0.2320 (4)	0.14983 (17)	0.0476 (7)
C10	0.49353 (13)	0.1971 (3)	0.11672 (16)	0.0427 (7)
C11	0.50962 (14)	0.0223 (4)	0.10883 (17)	0.0516 (7)
H11	0.5457	−0.0086	0.0853	0.062*
C12	0.47121 (16)	−0.1066 (4)	0.13646 (19)	0.0637 (9)
H12	0.4813	−0.2255	0.1321	0.076*
C13	0.41833 (17)	−0.0569 (4)	0.1702 (2)	0.0647 (9)
H13	0.3931	−0.1446	0.1891	0.078*

	U11	U22	U33	U12	U13	U23
Cu1	0.0330 (3)	0.0411 (3)	0.0496 (3)	−0.0060 (2)	0.0010 (2)	0.0007 (2)
Cl1	0.0740 (6)	0.0506 (5)	0.1082 (7)	−0.0009 (4)	0.0415 (5)	−0.0033 (4)
N1	0.0370 (13)	0.0402 (13)	0.0472 (13)	−0.0072 (10)	0.0046 (11)	−0.0018 (10)
N2	0.0575 (16)	0.0524 (17)	0.0704 (18)	−0.0181 (14)	0.0207 (14)	−0.0051 (14)
O1	0.0380 (11)	0.0423 (11)	0.0642 (12)	−0.0088 (9)	−0.0065 (10)	0.0060 (9)
O2	0.0574 (14)	0.0533 (13)	0.0852 (16)	−0.0221 (11)	−0.0004 (12)	0.0056 (12)
C1	0.0438 (17)	0.0451 (17)	0.0461 (17)	−0.0024 (14)	0.0034 (14)	0.0014 (13)
C2	0.0347 (15)	0.0508 (18)	0.0458 (15)	−0.0041 (14)	0.0009 (12)	−0.0008 (14)
C3	0.0342 (15)	0.0491 (17)	0.0437 (17)	−0.0069 (13)	0.0028 (14)	−0.0073 (14)
C4	0.0444 (18)	0.0483 (19)	0.0557 (19)	−0.0108 (14)	0.0059 (15)	−0.0065 (15)
C5	0.0393 (18)	0.065 (2)	0.070 (2)	−0.0177 (15)	0.0003 (16)	−0.0121 (17)
C6	0.0391 (19)	0.077 (2)	0.072 (2)	−0.0053 (17)	−0.0096 (16)	−0.0098 (19)
C7	0.0467 (19)	0.063 (2)	0.0586 (19)	−0.0025 (15)	−0.0063 (15)	0.0012 (15)
C8	0.082 (3)	0.060 (2)	0.095 (3)	−0.0335 (19)	0.016 (2)	−0.0060 (19)
C9	0.0486 (18)	0.0405 (17)	0.0553 (18)	−0.0050 (14)	0.0125 (15)	−0.0034 (14)
C10	0.0403 (17)	0.0442 (17)	0.0425 (16)	−0.0093 (13)	0.0016 (13)	0.0005 (13)
C11	0.0503 (18)	0.0469 (18)	0.0583 (18)	−0.0059 (15)	0.0096 (14)	−0.0011 (15)
C12	0.073 (2)	0.0439 (19)	0.075 (2)	−0.0104 (17)	0.0156 (19)	−0.0005 (17)
C13	0.075 (2)	0.047 (2)	0.076 (2)	−0.0255 (17)	0.022 (2)	−0.0016 (16)

Cu1—O1i	1.8951 (17)	C4—C5	1.378 (4)
Cu1—O1	1.8951 (17)	C5—C6	1.395 (4)
Cu1—N1	1.974 (2)	C5—H5	0.9300
Cu1—N1i	1.974 (2)	C6—C7	1.351 (4)
Cl1—C9	1.743 (3)	C6—H6	0.9300
N1—C1	1.309 (3)	C7—H7	0.9300
N1—C10	1.434 (3)	C8—H8A	0.9600
N2—C9	1.314 (3)	C8—H8B	0.9600
N2—C13	1.341 (4)	C8—H8C	0.9600
O1—C3	1.304 (3)	C9—C10	1.389 (4)
O2—C4	1.363 (3)	C10—C11	1.378 (4)
O2—C8	1.429 (3)	C11—C12	1.384 (4)
C1—C2	1.426 (3)	C11—H11	0.9300
C1—H1	0.9300	C12—C13	1.365 (4)
C2—C3	1.403 (4)	C12—H12	0.9300
C2—C7	1.416 (4)	C13—H13	0.9300
C3—C4	1.443 (4)
O1i—Cu1—O1	180.00 (14)	C7—C6—C5	120.3 (3)
O1i—Cu1—N1	88.30 (8)	C7—C6—H6	119.9
O1—Cu1—N1	91.70 (8)	C5—C6—H6	119.9
O1i—Cu1—N1i	91.70 (8)	C6—C7—C2	120.8 (3)
O1—Cu1—N1i	88.30 (8)	C6—C7—H7	119.6
N1—Cu1—N1i	180.00 (16)	C2—C7—H7	119.6
C1—N1—C10	115.2 (2)	O2—C8—H8A	109.5
C1—N1—Cu1	123.28 (18)	O2—C8—H8B	109.5
C10—N1—Cu1	121.36 (17)	H8A—C8—H8B	109.5
C9—N2—C13	116.5 (3)	O2—C8—H8C	109.5
C3—O1—Cu1	127.80 (17)	H8A—C8—H8C	109.5
C4—O2—C8	117.4 (2)	H8B—C8—H8C	109.5
N1—C1—C2	126.7 (3)	N2—C9—C10	125.1 (3)
N1—C1—H1	116.7	N2—C9—Cl1	115.2 (2)
C2—C1—H1	116.7	C10—C9—Cl1	119.6 (2)
C3—C2—C7	120.6 (3)	C11—C10—C9	117.0 (2)
C3—C2—C1	121.9 (2)	C11—C10—N1	122.5 (2)
C7—C2—C1	117.3 (3)	C9—C10—N1	120.5 (2)
O1—C3—C2	124.5 (2)	C10—C11—C12	119.0 (3)
O1—C3—C4	118.2 (3)	C10—C11—H11	120.5
C2—C3—C4	117.3 (2)	C12—C11—H11	120.5
O2—C4—C5	125.7 (3)	C13—C12—C11	119.1 (3)
O2—C4—C3	114.2 (2)	C13—C12—H12	120.5
C5—C4—C3	120.1 (3)	C11—C12—H12	120.5
C4—C5—C6	121.0 (3)	N2—C13—C12	123.3 (3)
C4—C5—H5	119.5	N2—C13—H13	118.3
C6—C5—H5	119.5	C12—C13—H13	118.3
O1i—Cu1—N1—C1	161.5 (2)	O2—C4—C5—C6	178.8 (3)
O1—Cu1—N1—C1	−18.5 (2)	C3—C4—C5—C6	−1.2 (4)
O1i—Cu1—N1—C10	−13.9 (2)	C4—C5—C6—C7	0.0 (5)
O1—Cu1—N1—C10	166.1 (2)	C5—C6—C7—C2	1.5 (5)
N1—Cu1—O1—C3	21.0 (2)	C3—C2—C7—C6	−1.7 (4)
N1i—Cu1—O1—C3	−159.0 (2)	C1—C2—C7—C6	−176.5 (3)
C10—N1—C1—C2	−175.3 (2)	C13—N2—C9—C10	−2.2 (5)
Cu1—N1—C1—C2	9.1 (4)	C13—N2—C9—Cl1	179.7 (2)
N1—C1—C2—C3	6.3 (4)	N2—C9—C10—C11	3.2 (4)
N1—C1—C2—C7	−179.0 (3)	Cl1—C9—C10—C11	−178.8 (2)
Cu1—O1—C3—C2	−13.0 (4)	N2—C9—C10—N1	−176.8 (3)
Cu1—O1—C3—C4	167.22 (18)	Cl1—C9—C10—N1	1.2 (4)
C7—C2—C3—O1	−179.3 (2)	C1—N1—C10—C11	−60.3 (3)
C1—C2—C3—O1	−4.8 (4)	Cu1—N1—C10—C11	115.4 (3)
C7—C2—C3—C4	0.4 (4)	C1—N1—C10—C9	119.7 (3)
C1—C2—C3—C4	175.0 (2)	Cu1—N1—C10—C9	−64.6 (3)
C8—O2—C4—C5	0.7 (4)	C9—C10—C11—C12	−2.2 (4)
C8—O2—C4—C3	−179.2 (2)	N1—C10—C11—C12	177.8 (2)
O1—C3—C4—O2	0.7 (4)	C10—C11—C12—C13	0.4 (5)
C2—C3—C4—O2	−179.0 (2)	C9—N2—C13—C12	0.2 (5)
O1—C3—C4—C5	−179.2 (2)	C11—C12—C13—N2	0.6 (5)
C2—C3—C4—C5	1.0 (4)