[5-Chloro-2-hydroxy-N'-(2-oxido-ben-zyl-idene)benzo-hy-dra-zidato]-pyridine-copper(II).

In the title complex, [Cu(C(14)H(9)ClN(2)O(3))(C(5)H(5)N)], the Cu(II) ion exhibits a distorted trans-CuN(2)O(2) square-planar geometry arising from the O,O,N-tridentate ligand and a pyridine mol-ecule. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal structure, weak inter-molecular C-H⋯π inter-actions generate a chain. The crystal studied was an inversion twin.

Related literature

For background on the coordination chemistry of salicyl­aldehyde-type ligands, see: Bai et al. (2005 ▶). For information on C—H⋯π inter­actions, see: Nishio (2004 ▶).

Experimental

Crystal data

[Cu(C14H9ClN2O3)(C5H5N)]

M = 431.32

Monoclinic,

a = 23.586 (2) Å

b = 4.8268 (6) Å

c = 17.88540 (18) Å

β = 120.809 (2)°

V = 1748.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.43 mm−1

T = 298 K

0.39 × 0.28 × 0.17 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T min = 0.606, T max = 0.793

4087 measured reflections

2273 independent reflections

1849 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.00

2273 reflections

244 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 725 Friedel pairs

Flack parameter: 0.50 (2)

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 I, global. DOI: 10.1107/S1600536809020546/hb2989sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020546/hb2989Isup2.hkl

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

[Cu(C14H9ClN2O3)(C5H5N)]	F(000) = 876
Mr = 431.32	Dx = 1.638 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 23.586 (2) Å	Cell parameters from 1781 reflections
b = 4.8268 (6) Å	θ = 2.7–23.7°
c = 17.88540 (18) Å	µ = 1.43 mm−1
β = 120.809 (2)°	T = 298 K
V = 1748.8 (3) Å3	Block, green
Z = 4	0.39 × 0.28 × 0.17 mm

Siemens SMART CCD diffractometer	2273 independent reflections
Radiation source: fine-focus sealed tube	1849 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −28→25
Tmin = 0.606, Tmax = 0.793	k = −5→5
4087 measured reflections	l = −17→21

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0729P)2 + 0.8658P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2273 reflections	Δρmax = 0.37 e Å−3
244 parameters	Δρmin = −0.19 e Å−3
2 restraints	Absolute structure: Flack (1983), 725 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.50 (2)

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	0.18179 (4)	0.48947 (15)	0.25227 (4)	0.0455 (2)
Cl1	0.00840 (11)	1.5179 (4)	−0.07019 (13)	0.0697 (5)
N1	0.0517 (3)	0.6161 (12)	0.2113 (3)	0.0462 (13)
N2	0.1052 (3)	0.4396 (12)	0.2649 (4)	0.0452 (14)
N3	0.2566 (3)	0.5850 (12)	0.2378 (4)	0.0487 (13)
O1	0.1235 (2)	0.7588 (9)	0.1676 (3)	0.0519 (11)
O2	−0.0618 (2)	0.8534 (11)	0.1447 (4)	0.0721 (14)
H2	−0.0319	0.7470	0.1764	0.108*
O3	0.2275 (2)	0.1945 (8)	0.3304 (3)	0.0509 (11)
C1	0.0675 (3)	0.7694 (13)	0.1643 (4)	0.0468 (15)
C2	0.0182 (3)	0.9709 (11)	0.1036 (4)	0.0438 (14)
C3	−0.0435 (4)	1.0041 (13)	0.0969 (5)	0.0545 (17)
C4	−0.0874 (3)	1.1994 (15)	0.0388 (5)	0.064 (2)
H4	−0.1282	1.2236	0.0343	0.076*
C5	−0.0718 (3)	1.3556 (16)	−0.0116 (5)	0.0611 (19)
H5	−0.1020	1.4840	−0.0503	0.073*
C6	−0.0118 (3)	1.3239 (12)	−0.0053 (4)	0.0502 (15)
C7	0.0333 (3)	1.1330 (13)	0.0522 (4)	0.0478 (15)
H7	0.0740	1.1134	0.0564	0.057*
C8	0.0986 (3)	0.2719 (14)	0.3155 (4)	0.0494 (16)
H8	0.0590	0.2752	0.3150	0.059*
C9	0.1478 (3)	0.0818 (12)	0.3722 (4)	0.0450 (15)
C10	0.2086 (3)	0.0513 (12)	0.3749 (4)	0.0460 (15)
C11	0.2519 (3)	−0.1564 (13)	0.4325 (5)	0.0539 (16)
H11	0.2920	−0.1860	0.4357	0.065*
C12	0.2365 (3)	−0.3133 (13)	0.4832 (4)	0.0576 (17)
H12	0.2661	−0.4472	0.5197	0.069*
C13	0.1771 (4)	−0.2753 (13)	0.4808 (4)	0.0579 (19)
H13	0.1671	−0.3797	0.5162	0.069*
C14	0.1341 (4)	−0.0825 (14)	0.4255 (5)	0.0540 (16)
H14	0.0940	−0.0587	0.4230	0.065*
C15	0.2503 (4)	0.7717 (17)	0.1806 (5)	0.069 (2)
H15	0.2091	0.8520	0.1452	0.083*
C16	0.3020 (4)	0.8541 (18)	0.1705 (6)	0.076 (2)
H16	0.2958	0.9905	0.1302	0.092*
C17	0.3626 (3)	0.7324 (16)	0.2205 (5)	0.0635 (18)
H17	0.3981	0.7803	0.2143	0.076*
C18	0.3687 (4)	0.5405 (17)	0.2790 (6)	0.080 (3)
H18	0.4090	0.4535	0.3143	0.095*
C19	0.3141 (4)	0.4733 (15)	0.2863 (6)	0.068 (2)
H19	0.3193	0.3431	0.3277	0.082*

	U11	U22	U33	U12	U13	U23
Cu1	0.0378 (3)	0.0493 (4)	0.0461 (4)	0.0027 (3)	0.0192 (3)	−0.0002 (4)
Cl1	0.0771 (12)	0.0676 (12)	0.0674 (12)	0.0189 (9)	0.0392 (10)	0.0148 (9)
N1	0.039 (3)	0.044 (3)	0.046 (3)	0.012 (3)	0.015 (3)	0.000 (3)
N2	0.036 (3)	0.052 (3)	0.038 (3)	0.000 (3)	0.012 (3)	−0.010 (3)
N3	0.045 (3)	0.051 (3)	0.053 (4)	0.002 (3)	0.027 (3)	0.002 (3)
O1	0.041 (2)	0.061 (3)	0.053 (3)	0.007 (2)	0.024 (2)	0.008 (2)
O2	0.060 (3)	0.079 (3)	0.090 (4)	0.019 (3)	0.048 (3)	0.013 (3)
O3	0.045 (2)	0.046 (2)	0.060 (3)	0.007 (2)	0.026 (2)	0.005 (2)
C1	0.041 (3)	0.045 (3)	0.044 (4)	0.002 (3)	0.013 (3)	−0.010 (3)
C2	0.040 (3)	0.044 (3)	0.044 (3)	0.004 (3)	0.019 (3)	−0.011 (3)
C3	0.047 (4)	0.057 (4)	0.061 (4)	0.005 (3)	0.028 (3)	−0.004 (3)
C4	0.046 (3)	0.068 (5)	0.072 (5)	0.013 (3)	0.027 (4)	−0.006 (4)
C5	0.049 (4)	0.062 (4)	0.057 (5)	0.020 (4)	0.016 (3)	−0.003 (4)
C6	0.054 (4)	0.045 (4)	0.043 (4)	0.006 (3)	0.019 (3)	−0.006 (3)
C7	0.041 (3)	0.049 (4)	0.049 (4)	0.005 (3)	0.019 (3)	−0.012 (3)
C8	0.045 (3)	0.054 (4)	0.054 (4)	−0.004 (3)	0.030 (3)	−0.009 (3)
C9	0.053 (3)	0.035 (3)	0.048 (4)	−0.003 (3)	0.026 (3)	−0.010 (3)
C10	0.048 (3)	0.038 (3)	0.048 (4)	−0.006 (3)	0.021 (3)	−0.010 (3)
C11	0.054 (4)	0.040 (3)	0.065 (4)	−0.005 (3)	0.028 (3)	−0.006 (3)
C12	0.060 (4)	0.043 (4)	0.057 (4)	0.003 (3)	0.021 (3)	−0.001 (3)
C13	0.069 (4)	0.053 (4)	0.050 (5)	−0.013 (4)	0.028 (4)	−0.005 (3)
C14	0.060 (4)	0.051 (4)	0.053 (4)	−0.003 (3)	0.031 (3)	−0.003 (3)
C15	0.050 (4)	0.083 (5)	0.067 (5)	0.015 (4)	0.024 (4)	0.017 (4)
C16	0.078 (5)	0.083 (5)	0.084 (6)	0.018 (5)	0.053 (5)	0.031 (5)
C17	0.052 (4)	0.081 (5)	0.062 (4)	−0.001 (4)	0.031 (3)	0.000 (4)
C18	0.047 (4)	0.095 (6)	0.092 (6)	0.009 (4)	0.033 (4)	0.033 (5)
C19	0.049 (4)	0.074 (6)	0.072 (6)	0.002 (3)	0.024 (4)	0.023 (4)

Cu1—O3	1.897 (4)	C7—H7	0.9300
Cu1—O1	1.934 (4)	C8—C9	1.419 (9)
Cu1—N2	1.945 (6)	C8—H8	0.9300
Cu1—N3	1.965 (6)	C9—C14	1.401 (10)
Cl1—C6	1.737 (7)	C9—C10	1.416 (9)
N1—C1	1.310 (9)	C10—C11	1.426 (10)
N1—N2	1.413 (8)	C11—C12	1.364 (10)
N2—C8	1.282 (9)	C11—H11	0.9300
N3—C19	1.296 (10)	C12—C13	1.393 (10)
N3—C15	1.313 (9)	C12—H12	0.9300
O1—C1	1.292 (7)	C13—C14	1.359 (9)
O2—C3	1.351 (9)	C13—H13	0.9300
O2—H2	0.8200	C14—H14	0.9300
O3—C10	1.293 (8)	C15—C16	1.380 (11)
C1—C2	1.478 (8)	C15—H15	0.9300
C2—C7	1.386 (10)	C16—C17	1.370 (10)
C2—C3	1.405 (10)	C16—H16	0.9300
C3—C4	1.393 (10)	C17—C18	1.349 (11)
C4—C5	1.362 (11)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.396 (12)
C5—C6	1.370 (10)	C18—H18	0.9300
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.385 (9)
O3—Cu1—O1	171.5 (2)	N2—C8—C9	124.1 (6)
O3—Cu1—N2	91.9 (2)	N2—C8—H8	117.9
O1—Cu1—N2	81.0 (2)	C9—C8—H8	117.9
O3—Cu1—N3	93.6 (2)	C14—C9—C10	120.1 (6)
O1—Cu1—N3	93.7 (2)	C14—C9—C8	117.5 (6)
N2—Cu1—N3	173.5 (3)	C10—C9—C8	122.4 (6)
C1—N1—N2	109.1 (5)	O3—C10—C9	125.8 (6)
C8—N2—N1	118.0 (6)	O3—C10—C11	118.4 (6)
C8—N2—Cu1	128.0 (5)	C9—C10—C11	115.8 (6)
N1—N2—Cu1	114.0 (4)	C12—C11—C10	122.4 (7)
C19—N3—C15	118.0 (7)	C12—C11—H11	118.8
C19—N3—Cu1	121.1 (6)	C10—C11—H11	118.8
C15—N3—Cu1	120.8 (5)	C11—C12—C13	120.8 (6)
C1—O1—Cu1	111.3 (4)	C11—C12—H12	119.6
C3—O2—H2	109.5	C13—C12—H12	119.6
C10—O3—Cu1	127.5 (4)	C14—C13—C12	118.5 (6)
O1—C1—N1	124.6 (5)	C14—C13—H13	120.7
O1—C1—C2	117.5 (6)	C12—C13—H13	120.7
N1—C1—C2	117.9 (5)	C13—C14—C9	122.4 (7)
C7—C2—C3	119.1 (6)	C13—C14—H14	118.8
C7—C2—C1	119.0 (6)	C9—C14—H14	118.8
C3—C2—C1	121.9 (6)	N3—C15—C16	123.0 (7)
O2—C3—C4	118.6 (7)	N3—C15—H15	118.5
O2—C3—C2	122.5 (6)	C16—C15—H15	118.5
C4—C3—C2	118.9 (7)	C17—C16—C15	119.1 (7)
C5—C4—C3	121.2 (7)	C17—C16—H16	120.4
C5—C4—H4	119.4	C15—C16—H16	120.4
C3—C4—H4	119.4	C18—C17—C16	117.6 (7)
C4—C5—C6	120.1 (6)	C18—C17—H17	121.2
C4—C5—H5	120.0	C16—C17—H17	121.2
C6—C5—H5	120.0	C17—C18—C19	119.6 (7)
C5—C6—C7	120.3 (7)	C17—C18—H18	120.2
C5—C6—Cl1	120.7 (5)	C19—C18—H18	120.2
C7—C6—Cl1	119.0 (5)	N3—C19—C18	122.7 (8)
C6—C7—C2	120.5 (6)	N3—C19—H19	118.7
C6—C7—H7	119.8	C18—C19—H19	118.7
C2—C7—H7	119.8
C1—N1—N2—C8	−179.6 (6)	O1—C1—C2—C3	−178.1 (6)
C1—N1—N2—Cu1	1.2 (6)	N1—C1—C2—C3	1.3 (9)
O3—Cu1—N2—C8	4.3 (6)	C7—C2—C3—O2	179.9 (6)
O1—Cu1—N2—C8	179.6 (6)	C7—C2—C3—C4	−0.1 (9)
N3—Cu1—N2—C8	−143 (2)	C1—C2—C3—C4	179.5 (6)
O3—Cu1—N2—N1	−176.6 (4)	O2—C3—C4—C5	−179.4 (7)
O1—Cu1—N2—N1	−1.2 (4)	C4—C5—C6—Cl1	179.1 (6)
N3—Cu1—N2—N1	36 (3)	C5—C6—C7—C2	0.4 (9)
O3—Cu1—N3—C19	−9.1 (7)	Cl1—C6—C7—C2	−178.7 (5)
O1—Cu1—N3—C19	175.1 (7)	C3—C2—C7—C6	−0.4 (9)
N2—Cu1—N3—C19	139 (2)	C1—C2—C7—C6	−180.0 (5)
O3—Cu1—N3—C15	173.4 (6)	N1—N2—C8—C9	179.5 (5)
O1—Cu1—N3—C15	−2.5 (6)	N2—C8—C9—C14	178.1 (6)
N2—Cu1—N3—C15	−39 (3)	Cu1—O3—C10—C9	1.9 (9)
O3—Cu1—O1—C1	34.5 (18)	Cu1—O3—C10—C11	−177.8 (4)
N2—Cu1—O1—C1	1.0 (4)	C14—C9—C10—O3	−178.4 (6)
N3—Cu1—O1—C1	−175.1 (4)	C8—C9—C10—O3	2.9 (9)
O1—Cu1—O3—C10	−37.5 (19)	C14—C9—C10—C11	1.3 (8)
N2—Cu1—O3—C10	−4.5 (5)	C8—C9—C10—C11	−177.4 (6)
N3—Cu1—O3—C10	172.0 (5)	O3—C10—C11—C12	178.6 (6)
Cu1—O1—C1—N1	−0.6 (7)	C9—C10—C11—C12	−1.0 (9)
Cu1—O1—C1—C2	178.7 (4)	C8—C9—C14—C13	178.5 (6)
N2—N1—C1—O1	−0.4 (8)	Cu1—N3—C15—C16	177.2 (7)
N2—N1—C1—C2	−179.7 (5)	N3—C15—C16—C17	1.7 (14)
O1—C1—C2—C7	1.4 (8)	Cu1—N3—C19—C18	−178.7 (7)
N1—C1—C2—C7	−179.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.85	2.575 (9)	147
C16—H16···Cg1i	0.93	2.81	3.48 (3)	130

Table 1

Selected bond lengths (Å)

Cu1—O3	1.897 (4)
Cu1—O1	1.934 (4)
Cu1—N2	1.945 (6)
Cu1—N3	1.965 (6)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1	0.82	1.85	2.575 (9)	147
C16—H16⋯Cg1i	0.93	2.81	3.48 (3)	130

Symmetry code: (i) . Cg1 is the centroid of the C9–C14 ring.