Chlorido[4-chloro-2-(pyridin-2-yl-methyl-imino-meth-yl)phenolato-κ(3)N,N',O]copper(II).

In the title complex, [Cu(C(13)H(10)ClN(2)O)Cl], the Cu(II) ion is coordinated by one O atom and two N atoms of the tridentate Schiff base ligand and one chloride ion, forming a slightly distorted square-planar geometry. Weak Cu⋯Cl inter-actions [2.793 (5) Å] result in the formation of a chain along the a axis.

Related literature

For background to the use of unsymmetrical tridentate Schiff base ligands and their hydrogenated derivatives in coordin­ation chemistry for the assembly of alkoxo-or phenoxo-bridged clusters and polymers, see: Koizumi et al. (2005 ▶); Boskovic et al. (2003 ▶); Oshiob et al. (2005 ▶). For related structures, see: Bluhm et al. (2003 ▶); Kannappan et al. (2005 ▶); Sun et al. (2005 ▶).

Experimental

Crystal data

[Cu(C13H10ClN2O)Cl]

M = 344.67

Orthorhombic,

a = 7.7975 (11) Å

b = 13.638 (2) Å

c = 24.854 (4) Å

V = 2643.1 (7) Å3

Z = 8

Mo Kα radiation

μ = 2.05 mm−1

T = 293 K

0.15 × 0.12 × 0.09 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.749, T max = 0.837

12098 measured reflections

2325 independent reflections

1580 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.098

S = 1.02

2325 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: SHELXTL (Sheldrick, 2008b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013359/hg5195sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013359/hg5195Isup2.hkl

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

[Cu(C13H10ClN2O)Cl]	F(000) = 1384
Mr = 344.67	Dx = 1.732 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1346 reflections
a = 7.7975 (11) Å	θ = 2.8–26.3°
b = 13.638 (2) Å	µ = 2.05 mm−1
c = 24.854 (4) Å	T = 293 K
V = 2643.1 (7) Å3	Block, blue
Z = 8	0.15 × 0.12 × 0.09 mm

Bruker APEXII diffractometer	2325 independent reflections
Radiation source: fine-focus sealed tube	1580 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −9→9
Tmin = 0.749, Tmax = 0.837	k = −14→16
12098 measured reflections	l = −27→29

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0418P)2 + 1.4463P] where P = (Fo2 + 2Fc2)/3
2325 reflections	(Δ/σ)max = 0.006
172 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.33 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	0.10863 (6)	0.97468 (3)	0.248134 (18)	0.03844 (17)
Cl1	0.43484 (19)	0.64978 (10)	0.45552 (5)	0.0755 (4)
Cl2	−0.09768 (12)	1.09117 (7)	0.25915 (4)	0.0441 (3)
O1	0.1221 (4)	0.9585 (2)	0.32421 (11)	0.0504 (8)
N1	0.2305 (4)	0.8517 (2)	0.23433 (11)	0.0349 (7)
N2	0.1071 (4)	0.9820 (2)	0.16720 (13)	0.0407 (8)
C1	0.2746 (5)	0.8043 (3)	0.32695 (15)	0.0358 (9)
C2	0.1939 (5)	0.8871 (3)	0.35062 (16)	0.0399 (10)
C3	0.1894 (6)	0.8900 (3)	0.40777 (17)	0.0524 (12)
H3	0.1355	0.9426	0.4246	0.063*
C4	0.2610 (6)	0.8186 (3)	0.43873 (17)	0.0564 (12)
H4	0.2573	0.8231	0.4760	0.068*
C5	0.3394 (5)	0.7391 (3)	0.41436 (17)	0.0472 (11)
C6	0.3446 (5)	0.7312 (3)	0.36013 (16)	0.0414 (10)
H6	0.3953	0.6764	0.3446	0.050*
C7	0.2900 (5)	0.7931 (3)	0.27008 (15)	0.0343 (9)
H7	0.3488	0.7381	0.2578	0.041*
C8	0.1920 (5)	0.9084 (3)	0.14267 (15)	0.0392 (10)
C9	0.2162 (6)	0.9091 (3)	0.08752 (17)	0.0544 (12)
H9	0.2736	0.8576	0.0709	0.065*
C10	0.1555 (6)	0.9855 (4)	0.05748 (19)	0.0655 (14)
H10	0.1727	0.9868	0.0205	0.079*
C11	0.0687 (6)	1.0606 (4)	0.08264 (19)	0.0646 (13)
H11	0.0268	1.1134	0.0630	0.077*
C12	0.0453 (6)	1.0559 (3)	0.13728 (17)	0.0535 (12)
H12	−0.0157	1.1057	0.1542	0.064*
C13	0.2559 (5)	0.8271 (3)	0.17772 (14)	0.0407 (10)
H13A	0.1948	0.7671	0.1693	0.049*
H13B	0.3770	0.8163	0.1709	0.049*

	U11	U22	U33	U12	U13	U23
Cu1	0.0423 (3)	0.0278 (3)	0.0452 (3)	0.0030 (2)	0.0022 (3)	−0.0004 (2)
Cl1	0.1064 (11)	0.0612 (8)	0.0589 (7)	0.0109 (8)	−0.0199 (7)	0.0129 (6)
Cl2	0.0358 (5)	0.0300 (5)	0.0665 (7)	0.0016 (4)	0.0006 (5)	−0.0014 (5)
O1	0.065 (2)	0.0367 (17)	0.0496 (17)	0.0140 (15)	0.0072 (15)	0.0007 (14)
N1	0.0397 (19)	0.0258 (17)	0.0392 (18)	−0.0030 (15)	0.0042 (15)	−0.0022 (14)
N2	0.040 (2)	0.0336 (19)	0.0484 (19)	−0.0033 (17)	−0.0025 (16)	0.0041 (16)
C1	0.034 (2)	0.028 (2)	0.045 (2)	−0.0045 (17)	0.0006 (18)	−0.0028 (18)
C2	0.041 (2)	0.032 (2)	0.047 (2)	−0.0053 (19)	0.004 (2)	−0.0024 (19)
C3	0.065 (3)	0.044 (3)	0.048 (3)	0.007 (2)	0.006 (2)	−0.007 (2)
C4	0.070 (3)	0.058 (3)	0.042 (2)	−0.005 (3)	0.002 (2)	−0.003 (2)
C5	0.052 (3)	0.041 (3)	0.048 (3)	−0.003 (2)	−0.004 (2)	0.003 (2)
C6	0.044 (3)	0.030 (2)	0.050 (3)	−0.0025 (18)	−0.0013 (19)	−0.003 (2)
C7	0.031 (2)	0.024 (2)	0.048 (2)	−0.0001 (17)	0.0022 (18)	−0.0048 (18)
C8	0.038 (2)	0.035 (2)	0.044 (2)	−0.0071 (19)	−0.0029 (19)	0.000 (2)
C9	0.063 (3)	0.051 (3)	0.049 (3)	0.000 (2)	0.000 (2)	−0.002 (2)
C10	0.078 (4)	0.074 (4)	0.045 (3)	−0.004 (3)	−0.005 (2)	0.009 (3)
C11	0.074 (4)	0.060 (3)	0.059 (3)	0.002 (3)	−0.008 (3)	0.016 (3)
C12	0.057 (3)	0.045 (3)	0.058 (3)	0.001 (2)	−0.001 (2)	0.004 (2)
C13	0.044 (3)	0.036 (2)	0.042 (2)	0.0012 (19)	0.001 (2)	−0.0045 (18)

Cu1—O1	1.907 (3)	C4—C5	1.384 (6)
Cu1—N1	1.958 (3)	C4—H4	0.9300
Cu1—N2	2.014 (3)	C5—C6	1.353 (5)
Cu1—Cl2	2.2775 (11)	C6—H6	0.9300
Cl1—C5	1.756 (4)	C7—H7	0.9300
O1—C2	1.300 (4)	C8—C9	1.383 (5)
N1—C7	1.282 (4)	C8—C13	1.495 (5)
N1—C13	1.460 (4)	C9—C10	1.367 (6)
N2—C12	1.342 (5)	C9—H9	0.9300
N2—C8	1.348 (5)	C10—C11	1.377 (6)
C1—C6	1.404 (5)	C10—H10	0.9300
C1—C2	1.421 (5)	C11—C12	1.372 (6)
C1—C7	1.427 (5)	C11—H11	0.9300
C2—C3	1.422 (5)	C12—H12	0.9300
C3—C4	1.362 (6)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
O1—Cu1—N1	92.74 (12)	C5—C6—C1	121.1 (4)
O1—Cu1—N2	175.25 (13)	C5—C6—H6	119.4
N1—Cu1—N2	82.55 (13)	C1—C6—H6	119.4
O1—Cu1—Cl2	90.03 (9)	N1—C7—C1	126.1 (4)
N1—Cu1—Cl2	164.03 (10)	N1—C7—H7	117.0
N2—Cu1—Cl2	94.67 (10)	C1—C7—H7	117.0
C2—O1—Cu1	127.7 (3)	N2—C8—C9	120.6 (4)
C7—N1—C13	118.4 (3)	N2—C8—C13	116.9 (3)
C7—N1—Cu1	126.0 (3)	C9—C8—C13	122.5 (4)
C13—N1—Cu1	115.6 (2)	C10—C9—C8	120.0 (4)
C12—N2—C8	119.0 (4)	C10—C9—H9	120.0
C12—N2—Cu1	126.4 (3)	C8—C9—H9	120.0
C8—N2—Cu1	114.3 (3)	C9—C10—C11	119.3 (5)
C6—C1—C2	119.6 (4)	C9—C10—H10	120.4
C6—C1—C7	118.2 (4)	C11—C10—H10	120.4
C2—C1—C7	122.2 (3)	C12—C11—C10	118.7 (5)
O1—C2—C1	125.2 (4)	C12—C11—H11	120.7
O1—C2—C3	118.2 (4)	C10—C11—H11	120.7
C1—C2—C3	116.5 (4)	N2—C12—C11	122.4 (4)
C4—C3—C2	122.3 (4)	N2—C12—H12	118.8
C4—C3—H3	118.8	C11—C12—H12	118.8
C2—C3—H3	118.8	N1—C13—C8	110.2 (3)
C3—C4—C5	119.6 (4)	N1—C13—H13A	109.6
C3—C4—H4	120.2	C8—C13—H13A	109.6
C5—C4—H4	120.2	N1—C13—H13B	109.6
C6—C5—C4	120.8 (4)	C8—C13—H13B	109.6
C6—C5—Cl1	120.8 (3)	H13A—C13—H13B	108.1
C4—C5—Cl1	118.4 (3)