Bis{μ-4-chloro-N′-[(E)-1-(5-chloro-2-oxidophen­yl)ethyl­idene]benzohydrazidato}bis­[pyridine­copper(II)]

Chang, J.-G.

doi:10.1107/S1600536811050720

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1886

https://doi.org/10.1107/S1600536811050720

Open

access

Bis{μ-4-chloro-N′-[(E)-1-(5-chloro-2-oxidophenyl)ethylidene]benzohydrazidato}bis[pyridinecopper(II)]

Jian-Guo Chang ^a ^*

^aDepartment of Materials Science and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: tsucjg@163.com

(Received 20 November 2011; accepted 25 November 2011; online 30 November 2011)

The crystal structure of the title complex, [Cu₂(C₁₅H₁₀Cl₂N₂O₂)₂(C₅H₅N)₂], features centrosymmetric dimers. The Cu^II ion is pentacoordinated in a quadratic pyramidal mode. The quadratic plane is formed by the O,O′,N-tridentate ligand and a pyridine molecule. The fifth coordination site is occupied by the O atom of another ligand showing a significantly longer Cu—O bond.

Related literature

For further details of the chemistry of the title compound, see: Salem (1998 ). For a related structure, see: Chang (2008 ).

Experimental

Crystal data

[Cu₂(C₁₅H₁₀Cl₂N₂O₂)₂(C₅H₅N)₂]
M_r = 927.58
Monoclinic, P 2₁ /c
a = 11.913 (2) Å
b = 8.0783 (16) Å
c = 19.997 (4) Å
β = 95.66 (3)°
V = 1915.1 (7) Å³
Z = 2
Mo Kα radiation
μ = 1.44 mm⁻¹
T = 298 K
0.28 × 0.25 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.688, T_max = 0.782
9685 measured reflections
3411 independent reflections
2976 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.064
S = 1.02
3411 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O2	1.8824 (14)
Cu1—O1	1.9209 (15)
Cu1—N2	1.9475 (17)
Cu1—N3	2.0275 (17)
Cu1—O2ⁱ	2.6055 (16)
Symmetry code: (i) -x, -y, -z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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 global, I. DOI: https://doi.org/10.1107/S1600536811050720/bt5720sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050720/bt5720Isup2.hkl

checkCIF report

Comment top

The chemistry of aroylhydrazones has gained a special attraction due to their coordination abilities to metal ions (Salem, 1998). As an extension of work on the structural characterization of aroylhydrazone derivatives (Chang, 2008), the title compound, (I), was synthesized and its crystal structure is reported here.

The new complex, (I), the Cu II ion exhibits a distorted trans-Cu₂O₂ square-planar geometry arising from the O, O, N-tridentate ligand and a pyridine molecule. (see Fig. 1).Two molecules form a weak-bridged dimer with weak Cu—O interactions. (see Fig. 2).

Related literature top

For further details of the chemistry of the title compound, see: Salem (1998). For a related structure, see: Chang (2008).

Experimental top

The ligand 4-chloro-N'-[(1E)-1-(5-chloro-2-hydroxyphenyl)ethylidene]benzohydrazide was prepared by the reaction of 1-(5-chloro-2-hydroxyphenyl)ethanone and 4-chlorobenzohydrazide in a molar ratio of 1:1 under reflux in ethanol for 4 h. The white precipitate was collected, washed several times with ethanol and dried in vacuo (yield 83%).A DMF solution (5 ml) of the ligand (0.25 mmol, 0.081 g) was mixed with a methanol solution(5 ml) of Cu(OAc)2 (0.25 mmol, 0.05 g). The mixture was stirred at 298 K for 4 h and then filtered. A blue precipitate was produced after about 10 d. A pyridine mixture (5 ml) was used to dissolve the precipitate at 330 K. Blue block-shaped crystals were obtained after one month (yield 25%).

Structure description top

For further details of the chemistry of the title compound, see: Salem (1998). For a related structure, see: Chang (2008).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 compound (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The dimeric structure of the title compound . H atoms have been omitted for clarity. [Dashed lines show Cu—O weak interactions].

Bis{µ-4-chloro-N'-[(E)-1-(5-chloro-2- oxidophenyl)ethylidene]benzohydrazidato}bis[pyridinecopper(II)] top

Crystal data top

[Cu₂(C₁₅H₁₀Cl₂N₂O₂)₂(C₅H₅N)₂]	F(000) = 940
M_r = 927.58	D_x = 1.609 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4831 reflections
a = 11.913 (2) Å	θ = 2.5–27.9°
b = 8.0783 (16) Å	µ = 1.44 mm⁻¹
c = 19.997 (4) Å	T = 298 K
β = 95.66 (3)°	Block, blue
V = 1915.1 (7) Å³	0.28 × 0.25 × 0.18 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	3411 independent reflections
Radiation source: fine-focus sealed tube	2976 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
φ and ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −13→14
T_min = 0.688, T_max = 0.782	k = −9→9
9685 measured reflections	l = −22→23

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)] = 0.026	H-atom parameters constrained
wR(F²) = 0.064	w = 1/[σ²(F_o²) + (0.0242P)² + 1.1862P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3411 reflections	Δρ_max = 0.22 e Å⁻³
255 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0011 (3)

Crystal data top

[Cu₂(C₁₅H₁₀Cl₂N₂O₂)₂(C₅H₅N)₂]	V = 1915.1 (7) Å³
M_r = 927.58	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.913 (2) Å	µ = 1.44 mm⁻¹
b = 8.0783 (16) Å	T = 298 K
c = 19.997 (4) Å	0.28 × 0.25 × 0.18 mm
β = 95.66 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3411 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2976 reflections with I > 2σ(I)
T_min = 0.688, T_max = 0.782	R_int = 0.023
9685 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.064	H-atom parameters constrained
S = 1.02	Δρ_max = 0.22 e Å⁻³
3411 reflections	Δρ_min = −0.23 e Å⁻³
255 parameters

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	0.09353 (2)	0.14880 (3)	0.017875 (12)	0.03476 (10)
Cl1	0.49728 (6)	0.08946 (11)	0.39268 (3)	0.0677 (2)
Cl2	0.23787 (6)	−0.18478 (10)	−0.29800 (3)	0.0638 (2)
C1	0.19626 (16)	−0.0360 (3)	−0.10969 (10)	0.0334 (4)
C2	0.24154 (18)	−0.0995 (3)	−0.16734 (10)	0.0389 (5)
H2	0.3158	−0.1368	−0.1638	0.047*
C13	0.43005 (18)	0.0975 (3)	0.31108 (10)	0.0425 (5)
C6	0.08344 (17)	0.0220 (3)	−0.11671 (10)	0.0349 (5)
C9	0.26194 (17)	0.1119 (3)	0.11379 (10)	0.0355 (5)
C10	0.32367 (17)	0.1101 (3)	0.18203 (10)	0.0350 (5)
C7	0.26861 (16)	−0.0379 (3)	−0.04553 (10)	0.0340 (4)
C3	0.17827 (19)	−0.1071 (3)	−0.22803 (10)	0.0425 (5)
C14	0.47580 (18)	0.0123 (3)	0.26053 (11)	0.0496 (6)
H14	0.5416	−0.0489	0.2696	0.060*
C12	0.33351 (19)	0.1898 (3)	0.29860 (11)	0.0439 (5)
H12	0.3045	0.2480	0.3331	0.053*
C16	−0.04746 (19)	0.3803 (3)	0.08770 (11)	0.0442 (5)
H16	0.0054	0.3580	0.1239	0.053*
C11	0.27997 (18)	0.1952 (3)	0.23412 (11)	0.0410 (5)
H11	0.2140	0.2564	0.2254	0.049*
C15	0.42230 (18)	0.0195 (3)	0.19631 (11)	0.0457 (6)
H15	0.4527	−0.0373	0.1619	0.055*
C5	0.02189 (19)	0.0115 (3)	−0.18052 (11)	0.0447 (5)
H5	−0.0523	0.0491	−0.1857	0.054*
C17	−0.1338 (2)	0.4880 (3)	0.09677 (13)	0.0531 (6)
H17	−0.1394	0.5365	0.1385	0.064*
C4	0.0679 (2)	−0.0524 (3)	−0.23534 (11)	0.0472 (6)
H4	0.0254	−0.0587	−0.2768	0.057*
C8	0.38055 (18)	−0.1255 (3)	−0.04096 (11)	0.0470 (6)
H8A	0.4069	−0.1434	0.0054	0.071*
H8B	0.4341	−0.0589	−0.0617	0.071*
H8C	0.3720	−0.2301	−0.0637	0.071*
C19	−0.20175 (18)	0.4478 (3)	−0.01709 (12)	0.0477 (6)
H19	−0.2536	0.4692	−0.0540	0.057*
C18	−0.21219 (19)	0.5235 (3)	0.04330 (13)	0.0515 (6)
H18	−0.2709	0.5971	0.0481	0.062*
C20	−0.11366 (17)	0.3397 (3)	−0.02264 (11)	0.0401 (5)
H20	−0.1077	0.2882	−0.0637	0.048*
O2	0.02859 (12)	0.07997 (19)	−0.06722 (7)	0.0410 (4)
O1	0.16834 (12)	0.19404 (19)	0.10550 (7)	0.0408 (4)
N2	0.23464 (13)	0.0347 (2)	0.00719 (8)	0.0347 (4)
N1	0.30604 (14)	0.0264 (2)	0.06694 (8)	0.0389 (4)
N3	−0.03615 (14)	0.3059 (2)	0.02877 (8)	0.0346 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03293 (15)	0.03761 (16)	0.03257 (15)	0.00326 (11)	−0.00261 (10)	−0.00316 (11)
Cl1	0.0542 (4)	0.1114 (6)	0.0349 (3)	−0.0007 (4)	−0.0088 (3)	−0.0007 (3)
Cl2	0.0581 (4)	0.0963 (5)	0.0374 (3)	−0.0031 (4)	0.0078 (3)	−0.0195 (3)
C1	0.0347 (11)	0.0345 (11)	0.0307 (10)	−0.0046 (9)	0.0023 (8)	0.0004 (9)
C2	0.0362 (11)	0.0438 (13)	0.0367 (11)	−0.0040 (9)	0.0041 (9)	−0.0007 (10)
C13	0.0376 (12)	0.0582 (14)	0.0304 (11)	−0.0076 (10)	−0.0039 (9)	0.0000 (10)
C6	0.0381 (11)	0.0345 (11)	0.0316 (11)	−0.0027 (9)	0.0009 (9)	0.0012 (9)
C9	0.0335 (11)	0.0367 (12)	0.0353 (11)	−0.0029 (9)	−0.0015 (9)	−0.0004 (9)
C10	0.0330 (10)	0.0374 (12)	0.0341 (11)	−0.0039 (9)	0.0007 (9)	−0.0034 (9)
C7	0.0329 (10)	0.0356 (11)	0.0336 (11)	−0.0051 (9)	0.0030 (8)	0.0001 (9)
C3	0.0475 (13)	0.0507 (14)	0.0298 (11)	−0.0068 (10)	0.0068 (9)	−0.0030 (10)
C14	0.0348 (12)	0.0676 (17)	0.0445 (13)	0.0090 (11)	−0.0053 (10)	−0.0052 (12)
C12	0.0475 (13)	0.0497 (14)	0.0349 (12)	0.0007 (11)	0.0062 (10)	−0.0066 (10)
C16	0.0432 (12)	0.0481 (14)	0.0404 (13)	0.0050 (10)	−0.0004 (10)	−0.0030 (10)
C11	0.0378 (12)	0.0446 (13)	0.0400 (12)	0.0041 (10)	0.0008 (9)	−0.0037 (10)
C15	0.0376 (12)	0.0615 (15)	0.0372 (12)	0.0080 (11)	−0.0004 (9)	−0.0107 (11)
C5	0.0394 (12)	0.0570 (15)	0.0360 (12)	0.0051 (11)	−0.0046 (9)	0.0027 (11)
C17	0.0502 (14)	0.0567 (16)	0.0528 (14)	0.0076 (12)	0.0071 (11)	−0.0121 (12)
C4	0.0502 (14)	0.0619 (16)	0.0281 (11)	−0.0018 (11)	−0.0039 (10)	0.0026 (11)
C8	0.0367 (12)	0.0669 (16)	0.0366 (12)	0.0067 (11)	−0.0011 (9)	−0.0077 (11)
C19	0.0350 (12)	0.0509 (14)	0.0557 (15)	0.0033 (10)	−0.0034 (10)	0.0052 (12)
C18	0.0365 (12)	0.0491 (14)	0.0697 (17)	0.0082 (11)	0.0092 (11)	−0.0007 (13)
C20	0.0369 (11)	0.0402 (12)	0.0424 (12)	−0.0003 (9)	0.0003 (9)	0.0013 (10)
O2	0.0348 (8)	0.0523 (9)	0.0348 (8)	0.0070 (7)	−0.0024 (6)	−0.0080 (7)
O1	0.0370 (8)	0.0468 (9)	0.0370 (8)	0.0084 (7)	−0.0043 (6)	−0.0071 (7)
N2	0.0331 (9)	0.0400 (10)	0.0298 (9)	−0.0012 (7)	−0.0028 (7)	−0.0018 (8)
N1	0.0337 (9)	0.0506 (11)	0.0309 (9)	0.0029 (8)	−0.0041 (7)	−0.0044 (8)
N3	0.0324 (9)	0.0340 (9)	0.0370 (10)	−0.0005 (7)	0.0005 (7)	0.0014 (8)

Geometric parameters (Å, º) top

Cu1—O2	1.8824 (14)	C14—C15	1.377 (3)
Cu1—O1	1.9209 (15)	C14—H14	0.9300
Cu1—N2	1.9475 (17)	C12—C11	1.382 (3)
Cu1—N3	2.0275 (17)	C12—H12	0.9300
Cu1—O2ⁱ	2.6055 (16)	C16—N3	1.342 (3)
Cl1—C13	1.747 (2)	C16—C17	1.373 (3)
Cl2—C3	1.747 (2)	C16—H16	0.9300
C1—C2	1.417 (3)	C11—H11	0.9300
C1—C6	1.417 (3)	C15—H15	0.9300
C1—C7	1.473 (3)	C5—C4	1.374 (3)
C2—C3	1.365 (3)	C5—H5	0.9300
C2—H2	0.9300	C17—C18	1.379 (3)
C13—C12	1.373 (3)	C17—H17	0.9300
C13—C14	1.379 (3)	C4—H4	0.9300
C6—O2	1.324 (2)	C8—H8A	0.9600
C6—C5	1.410 (3)	C8—H8B	0.9600
C9—O1	1.294 (2)	C8—H8C	0.9600
C9—N1	1.315 (3)	C19—C18	1.370 (3)
C9—C10	1.485 (3)	C19—C20	1.378 (3)
C10—C15	1.390 (3)	C19—H19	0.9300
C10—C11	1.391 (3)	C18—H18	0.9300
C7—N2	1.305 (3)	C20—N3	1.341 (3)
C7—C8	1.504 (3)	C20—H20	0.9300
C3—C4	1.381 (3)	N2—N1	1.398 (2)

O2—Cu1—O1	173.26 (6)	C12—C11—C10	120.7 (2)
O2—Cu1—N2	92.48 (7)	C12—C11—H11	119.7
O1—Cu1—N2	82.09 (7)	C10—C11—H11	119.7
O2—Cu1—N3	91.86 (7)	C14—C15—C10	121.2 (2)
O1—Cu1—N3	94.17 (7)	C14—C15—H15	119.4
N2—Cu1—N3	169.49 (7)	C10—C15—H15	119.4
C2—C1—C6	118.22 (18)	C4—C5—C6	122.1 (2)
C2—C1—C7	117.89 (18)	C4—C5—H5	118.9
C6—C1—C7	123.88 (18)	C6—C5—H5	118.9
C3—C2—C1	121.2 (2)	C16—C17—C18	119.2 (2)
C3—C2—H2	119.4	C16—C17—H17	120.4
C1—C2—H2	119.4	C18—C17—H17	120.4
C12—C13—C14	121.5 (2)	C5—C4—C3	119.1 (2)
C12—C13—Cl1	119.26 (17)	C5—C4—H4	120.4
C14—C13—Cl1	119.23 (18)	C3—C4—H4	120.4
O2—C6—C5	116.53 (18)	C7—C8—H8A	109.5
O2—C6—C1	125.16 (18)	C7—C8—H8B	109.5
C5—C6—C1	118.24 (19)	H8A—C8—H8B	109.5
O1—C9—N1	125.31 (18)	C7—C8—H8C	109.5
O1—C9—C10	117.72 (18)	H8A—C8—H8C	109.5
N1—C9—C10	116.95 (18)	H8B—C8—H8C	109.5
C15—C10—C11	118.53 (19)	C18—C19—C20	119.3 (2)
C15—C10—C9	121.73 (19)	C18—C19—H19	120.3
C11—C10—C9	119.68 (19)	C20—C19—H19	120.3
N2—C7—C1	119.81 (18)	C19—C18—C17	118.5 (2)
N2—C7—C8	120.39 (18)	C19—C18—H18	120.7
C1—C7—C8	119.80 (18)	C17—C18—H18	120.7
C2—C3—C4	121.1 (2)	N3—C20—C19	122.7 (2)
C2—C3—Cl2	119.72 (18)	N3—C20—H20	118.7
C4—C3—Cl2	119.21 (17)	C19—C20—H20	118.7
C15—C14—C13	118.8 (2)	C6—O2—Cu1	126.23 (13)
C15—C14—H14	120.6	C9—O1—Cu1	109.62 (13)
C13—C14—H14	120.6	C7—N2—N1	117.24 (16)
C13—C12—C11	119.2 (2)	C7—N2—Cu1	129.88 (14)
C13—C12—H12	120.4	N1—N2—Cu1	112.82 (12)
C11—C12—H12	120.4	C9—N1—N2	109.36 (16)
N3—C16—C17	122.8 (2)	C20—N3—C16	117.44 (18)
N3—C16—H16	118.6	C20—N3—Cu1	121.31 (14)
C17—C16—H16	118.6	C16—N3—Cu1	121.24 (14)

C6—C1—C2—C3	−0.8 (3)	C18—C19—C20—N3	−0.6 (3)
C7—C1—C2—C3	177.68 (19)	C5—C6—O2—Cu1	−166.71 (15)
C2—C1—C6—O2	177.84 (19)	C1—C6—O2—Cu1	16.1 (3)
C7—C1—C6—O2	−0.6 (3)	N2—Cu1—O2—C6	−17.20 (17)
C2—C1—C6—C5	0.7 (3)	N3—Cu1—O2—C6	153.23 (17)
C7—C1—C6—C5	−177.69 (19)	N1—C9—O1—Cu1	7.5 (3)
O1—C9—C10—C15	177.2 (2)	C10—C9—O1—Cu1	−170.89 (14)
N1—C9—C10—C15	−1.3 (3)	N2—Cu1—O1—C9	−7.65 (14)
O1—C9—C10—C11	0.0 (3)	N3—Cu1—O1—C9	−177.77 (14)
N1—C9—C10—C11	−178.6 (2)	C1—C7—N2—N1	178.98 (17)
C2—C1—C7—N2	172.96 (19)	C8—C7—N2—N1	−0.2 (3)
C6—C1—C7—N2	−8.6 (3)	C1—C7—N2—Cu1	1.9 (3)
C2—C1—C7—C8	−7.8 (3)	C8—C7—N2—Cu1	−177.31 (16)
C6—C1—C7—C8	170.6 (2)	O2—Cu1—N2—C7	8.57 (19)
C1—C2—C3—C4	0.3 (3)	O1—Cu1—N2—C7	−175.44 (19)
C1—C2—C3—Cl2	179.44 (17)	N3—Cu1—N2—C7	−105.7 (4)
C12—C13—C14—C15	−0.6 (4)	O2—Cu1—N2—N1	−168.59 (13)
Cl1—C13—C14—C15	−179.93 (19)	O1—Cu1—N2—N1	7.40 (13)
C14—C13—C12—C11	1.1 (4)	N3—Cu1—N2—N1	77.1 (4)
Cl1—C13—C12—C11	−179.58 (18)	O1—C9—N1—N2	−1.4 (3)
C13—C12—C11—C10	−0.8 (3)	C10—C9—N1—N2	176.98 (16)
C15—C10—C11—C12	0.0 (3)	C7—N2—N1—C9	176.99 (18)
C9—C10—C11—C12	177.4 (2)	Cu1—N2—N1—C9	−5.5 (2)
C13—C14—C15—C10	−0.2 (4)	C19—C20—N3—C16	0.8 (3)
C11—C10—C15—C14	0.5 (3)	C19—C20—N3—Cu1	−178.99 (17)
C9—C10—C15—C14	−176.8 (2)	C17—C16—N3—C20	−0.2 (3)
O2—C6—C5—C4	−177.5 (2)	C17—C16—N3—Cu1	179.63 (18)
C1—C6—C5—C4	−0.1 (3)	O2—Cu1—N3—C20	−10.18 (16)
N3—C16—C17—C18	−0.6 (4)	O1—Cu1—N3—C20	172.84 (16)
C6—C5—C4—C3	−0.5 (4)	N2—Cu1—N3—C20	104.2 (4)
C2—C3—C4—C5	0.4 (4)	O2—Cu1—N3—C16	170.03 (17)
Cl2—C3—C4—C5	−178.78 (19)	O1—Cu1—N3—C16	−6.95 (17)
C20—C19—C18—C17	−0.2 (4)	N2—Cu1—N3—C16	−75.6 (4)
C16—C17—C18—C19	0.8 (4)

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	[Cu₂(C₁₅H₁₀Cl₂N₂O₂)₂(C₅H₅N)₂]
M_r	927.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.913 (2), 8.0783 (16), 19.997 (4)
β (°)	95.66 (3)
V (Å³)	1915.1 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.44
Crystal size (mm)	0.28 × 0.25 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.688, 0.782
No. of measured, independent and observed [I > 2σ(I)] reflections	9685, 3411, 2976
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.064, 1.02
No. of reflections	3411
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O2	1.8824 (14)	Cu1—N3	2.0275 (17)
Cu1—O1	1.9209 (15)	Cu1—O2ⁱ	2.6055 (16)
Cu1—N2	1.9475 (17)

Symmetry code: (i) −x, −y, −z.

Acknowledgements

This project was supported by the Postgraduate Foundation of Taishan University (No. Y05–2–09)

References

Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin,USA. Google Scholar
Chang, J.-G. (2008). Acta Cryst. E64, o198. Web of Science CSD CrossRef IUCr Journals Google Scholar
Salem, A. A. (1998). Microchem. J. 60, 51–66. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1886

https://doi.org/10.1107/S1600536811050720

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

Bis{μ-4-chloro-N′-[(E)-1-(5-chloro-2-oxidophen­yl)ethyl­­idene]benzohydrazidato}bis­­[pyridine­copper(II)]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis{μ-4-chloro-N′-[(E)-1-(5-chloro-2-oxidophenyl)ethylidene]benzohydrazidato}bis[pyridinecopper(II)]