[5-Chloro-2-hydroxy-N′-(2-oxido­ben­zyl­idene)benzo­hy­dra­zidato]­pyridine­copper(II)

Li, P.; Li, D.; Shi, X.

doi:10.1107/S1600536809020546

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m738

doi:10.1107/S1600536809020546

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[5-Chloro-2-hydroxy-N′-(2-oxidobenzylidene)benzohydrazidato]pyridinecopper(II)

Piyong Li,^a Dacheng Li ^a ^* and Xuefeng Shi ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: lidacheng62@lcu.edu.cn

(Received 27 May 2009; accepted 29 May 2009; online 6 June 2009)

In the title complex, [Cu(C₁₄H₉ClN₂O₃)(C₅H₅N)], the Cu^II ion exhibits a distorted trans-CuN₂O₂ square-planar geometry arising from the O,O,N-tridentate ligand and a pyridine molecule. An intramolecular O—H⋯N hydrogen bond occurs. In the crystal structure, weak intermolecular C—H⋯π interactions 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_r = 431.32
Monoclinic, C c
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.116
S = 1.00
2273 reflections
244 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 725 Friedel pairs
Flack parameter: 0.50 (2)

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) $[x, -y+1, z-{\script{1\over 2}}]$ . Cg1 is the centroid of the C9–C14 ring.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020546/hb2989sup1.cif

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

checkCIF report

Comment top

The chemistry of aroylhydrazones has gained a special attraction due to their coordination abilities to metal ions (Bai et al.,2005). However, researches on the complexes with salicylaldehyde-5-chlorosalicylichydrazone have not reported. So we have synthesized a new complex(Fig.1), which has been characterized by X-ray diffraction and elemental analysis. The structure of the title complex, (I), contains one ligand molecule, one pyridine molecule and one copper(II). The copper(II) coordination environment in the complex exhibits a distorted quadrilateral geometry (Table 1). In the crystal packing, the complex molecules are linked into one-dimensional chain by intermolecular C—H···π interactions (Nishio, 2004) (Table 2, Fig. 2).

Related literature top

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 top

A solution of salicylaldehyde (1.46 g, 12 mmol) in ethanol (10 ml) was added to a solution of 5-chlorosalicylichydrazine (1.87 g, 10 mmol) in ehanol (10 ml). The mixture was refluxed for 3 h, and then the precipitate was collected, washed several times with ethanol and dried in vacuo (yield 75.6%). m.p. > 300 K. A solution of Cu(OAc)₂ (0.04 g, 0.2 mmol)in methanol (10 ml) was added to the mixture of salicylaldehyde -5-chlorosalicylichydrazone (0.058 g, 0.2 mmol)and sodium methylate (0.0324 g, 0.6 mmol) in pyridine (10 ml). A green solution was obtained after stirring for 4 h. After being filtrated, dimethyl ether was slowly diffused into the filtrate, then green blocks of (I) were obtained after several weeks (m.p. >400 K) Elemental analysis calculated for C₁₉H₁₄Cl₁N₃O₃Cu₁: C, 52.90; H, 3.27; N, 9.74. Found (%): C, 52.95; H, 3.19; N, 9.69

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing 40% probability displacement ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. View of the chains in (I). Intermolecular C—H···π are shown as dashed lines. Most of H atoms are omitted.

[5-Chloro-2-hydroxy-N'-(2- oxidobenzylidene)benzohydrazidato]pyridinecopper(II) top

Crystal data top

[Cu(C₁₄H₉ClN₂O₃)(C₅H₅N)]	F(000) = 876
M_r = 431.32	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0729P)² + 0.8658P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2273 reflections	Δρ_max = 0.37 e Å⁻³
244 parameters	Δρ_min = −0.19 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 725 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.50 (2)

Crystal data top

[Cu(C₁₄H₉ClN₂O₃)(C₅H₅N)]	V = 1748.8 (3) Å³
M_r = 431.32	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 23.586 (2) Å	µ = 1.43 mm⁻¹
b = 4.8268 (6) Å	T = 298 K
c = 17.88540 (18) Å	0.39 × 0.28 × 0.17 mm
β = 120.809 (2)°

Data collection top

Siemens SMART CCD diffractometer	2273 independent reflections
Absorption correction: multi-scan (SADABS; Siemens, 1996)	1849 reflections with I > 2σ(I)
T_min = 0.606, T_max = 0.793	R_int = 0.021
4087 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.116	Δρ_max = 0.37 e Å⁻³
S = 1.00	Δρ_min = −0.19 e Å⁻³
2273 reflections	Absolute structure: Flack (1983), 725 Friedel pairs
244 parameters	Absolute structure parameter: 0.50 (2)
2 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₄H₉ClN₂O₃)(C₅H₅N)]
M_r	431.32
Crystal system, space group	Monoclinic, Cc
Temperature (K)	298
a, b, c (Å)	23.586 (2), 4.8268 (6), 17.88540 (18)
β (°)	120.809 (2)
V (Å³)	1748.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.43
Crystal size (mm)	0.39 × 0.28 × 0.17

Data collection
Diffractometer	Siemens SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Siemens, 1996)
T_min, T_max	0.606, 0.793
No. of measured, independent and observed [I > 2σ(I)] reflections	4087, 2273, 1849
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.116, 1.00
No. of reflections	2273
No. of parameters	244
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.19
Absolute structure	Flack (1983), 725 Friedel pairs
Absolute structure parameter	0.50 (2)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

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) x, −y+1, z−1/2.

Acknowledgements

We acknowledge the National Natural Science Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (grant No. 2005ZX09) for financial support.

References

Bai, Y., Dang, D. B., Duan, C. Y., Song, Y. & Meng, Q. J. (2005). Inorg. Chem. 44, 5972–5974. Web of Science CSD CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Nishio, M. (2004). CrystEngComm, 6, 130–158. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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Volume 65| Part 7| July 2009| Page m738

doi:10.1107/S1600536809020546

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

[5-Chloro-2-hy­droxy-N′-(2-oxido­ben­zyl­­idene)benzo­hy­dra­zidato]­pyridine­copper(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

[5-Chloro-2-hydroxy-N′-(2-oxidobenzylidene)benzohydrazidato]pyridinecopper(II)