Bis{(E)-4-chloro-2-[(2-chloro-3-pyrid­yl)imino­methyl-κN]phenolato-κO}copper(II)

Ding, Y.-J.; Tong, J.-F.; Dong, W.-K.; Sun, Y.-X.; Yao, J.

doi:10.1107/S1600536809029651

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m1013

doi:10.1107/S1600536809029651

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Bis{(E)-4-chloro-2-[(2-chloro-3-pyridyl)iminomethyl-κN]phenolato-κO}copper(II)

Yu-Jie Ding,^a Jun-Feng Tong,^b Wen-Kui Dong,^b ^* Yin-Xia Sun ^b and Jian Yao ^b

^aDepartment of Biochemical Engineering, Anhui University of Technology and Science, Wuhu 241000, People's Republic of China, and ^bSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: dongwk@mail.lzjtu.cn

(Received 23 July 2009; accepted 24 July 2009; online 31 July 2009)

In the title complex, [Cu(C₁₂H₇Cl₂N₂O)₂], the Cu^II center is tetracoordinated by two phenolic O and two azomethine N atoms from two bidentate 4-chloro-2-[(2-chloro-3-pyridyl)iminomethyl]phenolate (L) ligands. In the crystal structure, the Cu^II atom has a distorted square-planar coordination environment. The dihedral angles between the benzene and pyridyl rings are 54.39 (3) and 80.14 (4)°, indicating that the pyridine ring has a considerably weaker steric hindrance. The packing of the molecule is controlled by C—H⋯π(Ph) interactions and short O⋯Cl interactions [3.196 (4) Å], linking the molecules into a chain-like structure along the c axis.

Related literature

For background to Schiff bases, see: Soliman & Mohamed (2004 ); Abd El-Wahab et al. (2004 ). For the synthesis, see: Dong et al. (2009d ). For related structures, see: Dong et al. (2009a ,b ,c ).

Experimental

Crystal data

[Cu(C₁₂H₇Cl₂N₂O)₂]
M_r = 595.73
Monoclinic, P 2₁ /c
a = 20.236 (2) Å
b = 11.4821 (14) Å
c = 10.5458 (9) Å
β = 90.132 (2)°
V = 2450.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.36 mm⁻¹
T = 298 K
0.40 × 0.14 × 0.09 mm

Data collection

Buker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.613, T_max = 0.888
12294 measured reflections
4320 independent reflections
2614 reflections with I > 2σ(I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.065
S = 1.02
4320 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22⋯Cg1ⁱ	0.93	2.89	3.753 (3)	155
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C2–C7 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 global, I. DOI: 10.1107/S1600536809029651/at2850sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029651/at2850Isup2.hkl

checkCIF report

Comment top

Schiff bases are a versatile class of ligands in the field of modern coordination chemistry (Soliman & Mohamed, 2004), which can coordinate to transition or rare earth ions yielding complexes with interesting properties that are useful in materials science and in biological systems (Abd El-Wahab et al., 2004). As an extension of our work on the complexes between transition metals and Schiff base ligands (Dong et al., 2009a; Dong et al., 2009b), we report here the synthesis and crystal structures of the title complex, bis{(E)-[4-chloro-2-((2-chloropyridin-3-ylimino)methyl-κN)] phenolato-κO¹}copper(II) (Fig. 1).

In asymmetric molecule unit of the title complex, the Cu^II center is tetracoordinated by two phenolic O and two azomethine N atoms from two ligand (L^-) units and has a distorted square-planar coordination environment, which is similar to the reported copper complex with (E)-[4-bromo-2-((2-chloropyridin-3-ylimino)methyl)]phenol (Dong et al., 2009c). The interplane dihedral angles are found to be as follows: 54.39 (3)° between the benzene ring (C2—C7) and pyridyl ring (N2/C8—C12), 80.14 (4)° between benzene ring (C14—C19) and pyridyl ring (N4/C20—C24), indicating the pyridine ring having a considerable weaker steric hindrance. Besides, the dihedral angle between the coordination plane of O1—Cu1—N1 and O2—Cu1—N3 is 27.96 (3)°, indicating slight distortion toward tetrahedral geometry from the square planar structure. The packing of the molecule is controlled by C—H···π(Ph) interactions and short O···Cl interactions linking molecules into infinite one-dimensional supramolecular structure along c axis (Fig. 2).

Related literature top

For background to Schiff bases, see: Soliman & Mohamed (2004); Abd El-Wahab et al. (2004). For the synthesis, see: Dong et al. (2009d). For related structures, see: Dong et al. (2009a,b,c).

Experimental top

(E)-[4-Chloro-2-((2-chloropyridin-3-ylimino)methyl)]phenol (HL) was prepared according to previously reported procedure (Dong et al., 2009d). A blue solution of copper(II) acetate monohydrate (4.2 mg, 0.021 mmol) in ethanol (2 ml) was added dropwise to a pale-yellow solution of HL (11.2 mg, 0.042 mmol) in ethanol (4 ml) at room temperature. The colour of the mixing solution turned to brown immediately, then allowed to stand at room temperature for several days. With evaporation of the solvent, brown needle-like single crystals suitable for X-ray crystallographic analysis were obtained. IR: ν C=N, 1610 cm^-1, ν Ar—O, 1236 cm^-1, ν Cu—N, 459 cm^-1 and ν Cu—O, 426 cm^-1.

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 the title complex with atom numbering scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.
	Fig. 2. The infinite one-dimensional supramolecular structure along c axis linked by C—H···π(Ph) interactions and short O···Cl interactions (dashed lines).

Bis{(E)-4-chloro-2-[(2-chloro-3-pyridyl)iminomethyl- κN]phenolato-κO}copper(II) top

Crystal data top

[Cu(C₁₂H₇Cl₂N₂O)₂]	F(000) = 1196
M_r = 595.73	D_x = 1.615 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2435 reflections
a = 20.236 (2) Å	θ = 26.2–25.3°
b = 11.4821 (14) Å	µ = 1.36 mm⁻¹
c = 10.5458 (9) Å	T = 298 K
β = 90.132 (2)°	Needle-like, brown
V = 2450.3 (4) Å³	0.40 × 0.14 × 0.09 mm
Z = 4

Data collection top

Buker SMART 1000 CCD area-detector diffractometer	4320 independent reflections
Radiation source: fine-focus sealed tube	2614 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→19
T_min = 0.613, T_max = 0.888	k = −13→13
12294 measured reflections	l = −12→12

Refinement top

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.065	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0103P)²] where P = (F_o² + 2F_c²)/3
4320 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Cu(C₁₂H₇Cl₂N₂O)₂]	V = 2450.3 (4) Å³
M_r = 595.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.236 (2) Å	µ = 1.36 mm⁻¹
b = 11.4821 (14) Å	T = 298 K
c = 10.5458 (9) Å	0.40 × 0.14 × 0.09 mm
β = 90.132 (2)°

Data collection top

Buker SMART 1000 CCD area-detector diffractometer	4320 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2614 reflections with I > 2σ(I)
T_min = 0.613, T_max = 0.888	R_int = 0.058
12294 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.065	H-atom parameters constrained
S = 1.02	Δρ_max = 0.42 e Å⁻³
4320 reflections	Δρ_min = −0.39 e Å⁻³
316 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	0.75122 (2)	0.77649 (3)	0.42109 (4)	0.04479 (14)
Cl1	0.85318 (5)	0.19528 (7)	0.24296 (11)	0.0748 (4)
Cl2	0.69809 (5)	0.87831 (8)	0.16425 (10)	0.0715 (3)
Cl3	0.63434 (5)	1.36121 (8)	0.53290 (13)	0.0847 (4)
Cl4	0.87717 (5)	0.87627 (9)	0.20907 (10)	0.0712 (3)
N1	0.69574 (13)	0.6664 (2)	0.3246 (3)	0.0404 (7)
N2	0.5723 (2)	0.8484 (3)	0.1640 (4)	0.0824 (12)
N3	0.81090 (13)	0.9095 (2)	0.4590 (3)	0.0405 (7)
N4	0.97911 (16)	0.8403 (3)	0.3522 (3)	0.0580 (9)
O1	0.82307 (10)	0.67264 (18)	0.4291 (2)	0.0496 (7)
O2	0.67527 (11)	0.85984 (17)	0.4727 (2)	0.0475 (7)
C1	0.71125 (17)	0.5582 (3)	0.3021 (3)	0.0434 (9)
H1	0.6795	0.5116	0.2634	0.052*
C2	0.77345 (17)	0.5055 (3)	0.3324 (3)	0.0402 (9)
C3	0.82696 (17)	0.5658 (3)	0.3882 (3)	0.0387 (9)
C4	0.88764 (17)	0.5059 (3)	0.3980 (3)	0.0493 (10)
H4	0.9234	0.5434	0.4355	0.059*
C5	0.89566 (19)	0.3951 (3)	0.3546 (4)	0.0515 (10)
H5	0.9366	0.3587	0.3612	0.062*
C6	0.8432 (2)	0.3370 (3)	0.3011 (4)	0.0507 (11)
C7	0.78289 (18)	0.3887 (3)	0.2908 (3)	0.0479 (10)
H7	0.7476	0.3474	0.2564	0.057*
C8	0.62746 (19)	0.8039 (3)	0.2075 (4)	0.0560 (11)
C9	0.63246 (18)	0.7033 (3)	0.2809 (3)	0.0459 (10)
C10	0.5749 (2)	0.6457 (3)	0.3112 (4)	0.0635 (12)
H10	0.5757	0.5791	0.3614	0.076*
C11	0.5154 (2)	0.6894 (4)	0.2649 (5)	0.0825 (15)
H11	0.4756	0.6519	0.2810	0.099*
C12	0.5177 (3)	0.7896 (5)	0.1948 (5)	0.0967 (18)
H12	0.4777	0.8195	0.1661	0.116*
C13	0.79004 (17)	1.0141 (3)	0.4799 (3)	0.0432 (9)
H13	0.8221	1.0711	0.4922	0.052*
C14	0.72224 (17)	1.0512 (3)	0.4859 (3)	0.0398 (9)
C15	0.66883 (18)	0.9718 (3)	0.4849 (3)	0.0421 (9)
C16	0.60489 (17)	1.0190 (3)	0.5003 (3)	0.0522 (11)
H16	0.5688	0.9689	0.5007	0.063*
C17	0.59427 (18)	1.1356 (3)	0.5146 (4)	0.0575 (11)
H17	0.5515	1.1639	0.5245	0.069*
C18	0.64736 (19)	1.2118 (3)	0.5142 (4)	0.0531 (11)
C19	0.71064 (18)	1.1714 (3)	0.5010 (3)	0.0489 (10)
H19	0.7459	1.2233	0.5021	0.059*
C20	0.91648 (19)	0.8681 (3)	0.3548 (4)	0.0453 (10)
C21	0.88043 (17)	0.8917 (3)	0.4636 (4)	0.0403 (9)
C22	0.91409 (18)	0.8877 (3)	0.5758 (4)	0.0525 (10)
H22	0.8923	0.9029	0.6516	0.063*
C23	0.98051 (19)	0.8610 (3)	0.5768 (4)	0.0582 (11)
H23	1.0044	0.8594	0.6522	0.070*
C24	1.01031 (19)	0.8367 (3)	0.4626 (5)	0.0594 (12)
H24	1.0548	0.8166	0.4631	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0435 (3)	0.0421 (2)	0.0487 (3)	0.0027 (2)	−0.0027 (2)	−0.0051 (3)
Cl1	0.0885 (8)	0.0468 (6)	0.0891 (9)	0.0160 (6)	0.0088 (7)	−0.0087 (6)
Cl2	0.0949 (9)	0.0575 (6)	0.0622 (8)	0.0006 (6)	−0.0049 (6)	0.0104 (6)
Cl3	0.0771 (8)	0.0416 (5)	0.1354 (12)	0.0083 (5)	0.0144 (8)	−0.0066 (7)
Cl4	0.0742 (8)	0.0955 (7)	0.0439 (7)	0.0157 (6)	0.0002 (6)	−0.0041 (6)
N1	0.0402 (19)	0.0404 (17)	0.041 (2)	0.0038 (14)	−0.0034 (15)	−0.0013 (15)
N2	0.077 (3)	0.082 (3)	0.088 (3)	0.029 (2)	−0.037 (3)	−0.017 (2)
N3	0.0379 (19)	0.0411 (16)	0.042 (2)	0.0045 (14)	−0.0024 (15)	−0.0052 (15)
N4	0.047 (2)	0.067 (2)	0.060 (3)	0.0051 (18)	0.0065 (19)	−0.003 (2)
O1	0.0427 (15)	0.0416 (13)	0.0644 (19)	0.0052 (12)	−0.0101 (13)	−0.0088 (13)
O2	0.0440 (15)	0.0368 (13)	0.0616 (19)	0.0004 (12)	0.0039 (13)	−0.0083 (13)
C1	0.042 (2)	0.047 (2)	0.041 (3)	−0.0048 (19)	−0.0006 (19)	0.0013 (19)
C2	0.042 (2)	0.040 (2)	0.038 (2)	0.0023 (18)	0.0029 (19)	−0.0009 (19)
C3	0.038 (2)	0.044 (2)	0.035 (2)	0.0022 (18)	0.0044 (18)	0.0038 (19)
C4	0.041 (2)	0.056 (2)	0.051 (3)	0.006 (2)	−0.0053 (19)	0.002 (2)
C5	0.052 (3)	0.050 (2)	0.052 (3)	0.017 (2)	0.006 (2)	0.007 (2)
C6	0.062 (3)	0.040 (2)	0.050 (3)	0.014 (2)	0.008 (2)	0.000 (2)
C7	0.058 (3)	0.045 (2)	0.041 (3)	0.000 (2)	0.002 (2)	0.0018 (19)
C8	0.058 (3)	0.057 (3)	0.053 (3)	0.021 (2)	−0.010 (2)	−0.012 (2)
C9	0.044 (3)	0.052 (2)	0.042 (3)	0.010 (2)	−0.006 (2)	−0.011 (2)
C10	0.047 (3)	0.074 (3)	0.069 (3)	0.004 (2)	−0.003 (2)	−0.018 (2)
C11	0.047 (3)	0.107 (4)	0.094 (4)	0.001 (3)	−0.004 (3)	−0.031 (3)
C12	0.060 (4)	0.120 (5)	0.109 (5)	0.040 (4)	−0.035 (3)	−0.038 (4)
C13	0.044 (2)	0.045 (2)	0.041 (3)	−0.0035 (19)	0.0015 (19)	0.0000 (19)
C14	0.038 (2)	0.041 (2)	0.040 (2)	0.0049 (18)	0.0003 (18)	−0.0015 (18)
C15	0.040 (2)	0.048 (2)	0.038 (2)	0.0036 (19)	−0.0011 (18)	−0.0047 (19)
C16	0.041 (2)	0.048 (2)	0.067 (3)	−0.0001 (19)	0.002 (2)	−0.001 (2)
C17	0.046 (3)	0.053 (2)	0.074 (3)	0.006 (2)	−0.001 (2)	−0.004 (2)
C18	0.050 (3)	0.035 (2)	0.074 (3)	0.008 (2)	0.003 (2)	−0.006 (2)
C19	0.049 (2)	0.042 (2)	0.056 (3)	−0.0046 (19)	−0.001 (2)	0.003 (2)
C20	0.050 (3)	0.043 (2)	0.043 (3)	0.0017 (19)	0.001 (2)	−0.0012 (19)
C21	0.042 (2)	0.036 (2)	0.043 (3)	−0.0001 (18)	−0.001 (2)	−0.0007 (19)
C22	0.053 (3)	0.056 (2)	0.048 (3)	0.000 (2)	−0.002 (2)	0.000 (2)
C23	0.050 (3)	0.061 (2)	0.063 (3)	−0.003 (2)	−0.014 (2)	0.007 (2)
C24	0.044 (3)	0.057 (3)	0.077 (4)	−0.002 (2)	0.004 (3)	0.005 (3)

Geometric parameters (Å, º) top

Cu1—O1	1.882 (2)	C6—C7	1.361 (4)
Cu1—O2	1.892 (2)	C7—H7	0.9300
Cu1—N1	1.972 (3)	C8—C9	1.394 (5)
Cu1—N3	1.987 (3)	C9—C10	1.379 (4)
Cl1—C6	1.751 (3)	C10—C11	1.391 (5)
Cl2—C8	1.727 (4)	C10—H10	0.9300
Cl3—C18	1.747 (3)	C11—C12	1.368 (6)
Cl4—C20	1.731 (4)	C11—H11	0.9300
N1—C1	1.303 (3)	C12—H12	0.9300
N1—C9	1.424 (4)	C13—C14	1.438 (4)
N2—C8	1.309 (4)	C13—H13	0.9300
N2—C12	1.336 (5)	C14—C19	1.409 (4)
N3—C13	1.292 (3)	C14—C15	1.414 (4)
N3—C21	1.422 (4)	C15—C16	1.413 (4)
N4—C20	1.307 (4)	C16—C17	1.365 (4)
N4—C24	1.324 (5)	C16—H16	0.9300
O1—C3	1.303 (3)	C17—C18	1.385 (4)
O2—C15	1.298 (3)	C17—H17	0.9300
C1—C2	1.432 (4)	C18—C19	1.369 (4)
C1—H1	0.9300	C19—H19	0.9300
C2—C3	1.413 (4)	C20—C21	1.388 (4)
C2—C7	1.423 (4)	C21—C22	1.365 (5)
C3—C4	1.411 (4)	C22—C23	1.379 (4)
C4—C5	1.362 (4)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.376 (5)
C5—C6	1.374 (5)	C23—H23	0.9300
C5—H5	0.9300	C24—H24	0.9300

O1—Cu1—O2	159.31 (10)	C9—C10—H10	120.8
O1—Cu1—N1	93.20 (11)	C11—C10—H10	120.8
O2—Cu1—N1	90.63 (10)	C12—C11—C10	117.6 (5)
O1—Cu1—N3	90.50 (10)	C12—C11—H11	121.2
O2—Cu1—N3	92.70 (10)	C10—C11—H11	121.2
N1—Cu1—N3	160.32 (11)	N2—C12—C11	125.8 (5)
C1—N1—C9	116.2 (3)	N2—C12—H12	117.1
C1—N1—Cu1	124.6 (3)	C11—C12—H12	117.1
C9—N1—Cu1	119.1 (2)	N3—C13—C14	126.5 (3)
C8—N2—C12	115.0 (4)	N3—C13—H13	116.7
C13—N3—C21	116.8 (3)	C14—C13—H13	116.7
C13—N3—Cu1	123.4 (2)	C19—C14—C15	120.3 (3)
C21—N3—Cu1	119.8 (2)	C19—C14—C13	117.0 (3)
C20—N4—C24	116.7 (3)	C15—C14—C13	122.5 (3)
C3—O1—Cu1	129.0 (2)	O2—C15—C16	118.9 (3)
C15—O2—Cu1	127.7 (2)	O2—C15—C14	124.2 (3)
N1—C1—C2	125.1 (3)	C16—C15—C14	116.9 (3)
N1—C1—H1	117.5	C17—C16—C15	122.3 (3)
C2—C1—H1	117.5	C17—C16—H16	118.9
C3—C2—C7	119.1 (3)	C15—C16—H16	118.9
C3—C2—C1	123.9 (3)	C16—C17—C18	119.8 (3)
C7—C2—C1	116.6 (3)	C16—C17—H17	120.1
O1—C3—C4	119.2 (3)	C18—C17—H17	120.1
O1—C3—C2	123.6 (3)	C19—C18—C17	120.8 (3)
C4—C3—C2	117.3 (3)	C19—C18—Cl3	119.0 (3)
C5—C4—C3	122.3 (4)	C17—C18—Cl3	120.2 (3)
C5—C4—H4	118.8	C18—C19—C14	119.9 (3)
C3—C4—H4	118.8	C18—C19—H19	120.0
C4—C5—C6	119.9 (3)	C14—C19—H19	120.0
C4—C5—H5	120.0	N4—C20—C21	125.2 (4)
C6—C5—H5	120.0	N4—C20—Cl4	116.0 (3)
C7—C6—C5	120.9 (3)	C21—C20—Cl4	118.8 (3)
C7—C6—Cl1	118.8 (3)	C22—C21—C20	116.6 (3)
C5—C6—Cl1	120.3 (3)	C22—C21—N3	121.7 (3)
C6—C7—C2	120.5 (3)	C20—C21—N3	121.4 (4)
C6—C7—H7	119.8	C21—C22—C23	119.9 (4)
C2—C7—H7	119.8	C21—C22—H22	120.1
N2—C8—C9	125.4 (4)	C23—C22—H22	120.1
N2—C8—Cl2	114.8 (4)	C24—C23—C22	117.9 (4)
C9—C8—Cl2	119.8 (3)	C24—C23—H23	121.0
C10—C9—C8	117.8 (4)	C22—C23—H23	121.0
C10—C9—N1	122.8 (4)	N4—C24—C23	123.6 (4)
C8—C9—N1	119.4 (3)	N4—C24—H24	118.2
C9—C10—C11	118.4 (4)	C23—C24—H24	118.2

O1—Cu1—N1—C1	8.0 (3)	C1—N1—C9—C10	53.3 (5)
O2—Cu1—N1—C1	−151.7 (3)	Cu1—N1—C9—C10	−123.5 (3)
N3—Cu1—N1—C1	108.5 (4)	C1—N1—C9—C8	−128.7 (3)
O1—Cu1—N1—C9	−175.6 (3)	Cu1—N1—C9—C8	54.5 (4)
O2—Cu1—N1—C9	24.8 (3)	C8—C9—C10—C11	1.3 (5)
N3—Cu1—N1—C9	−75.0 (4)	N1—C9—C10—C11	179.3 (3)
O1—Cu1—N3—C13	−173.1 (3)	C9—C10—C11—C12	−1.9 (6)
O2—Cu1—N3—C13	−13.5 (3)	C8—N2—C12—C11	−0.6 (7)
N1—Cu1—N3—C13	85.9 (4)	C10—C11—C12—N2	1.7 (8)
O1—Cu1—N3—C21	7.2 (3)	C21—N3—C13—C14	−176.9 (3)
O2—Cu1—N3—C21	166.8 (3)	Cu1—N3—C13—C14	3.4 (5)
N1—Cu1—N3—C21	−93.7 (4)	N3—C13—C14—C19	−175.7 (4)
O2—Cu1—O1—C3	96.9 (4)	N3—C13—C14—C15	8.2 (6)
N1—Cu1—O1—C3	−3.4 (3)	Cu1—O2—C15—C16	167.6 (2)
N3—Cu1—O1—C3	−164.1 (3)	Cu1—O2—C15—C14	−13.5 (5)
O1—Cu1—O2—C15	117.5 (3)	C19—C14—C15—O2	−179.2 (3)
N1—Cu1—O2—C15	−141.7 (3)	C13—C14—C15—O2	−3.3 (6)
N3—Cu1—O2—C15	18.9 (3)	C19—C14—C15—C16	−0.3 (5)
C9—N1—C1—C2	176.8 (3)	C13—C14—C15—C16	175.6 (3)
Cu1—N1—C1—C2	−6.7 (5)	O2—C15—C16—C17	179.5 (3)
N1—C1—C2—C3	−1.7 (5)	C14—C15—C16—C17	0.5 (6)
N1—C1—C2—C7	−175.0 (3)	C15—C16—C17—C18	0.0 (6)
Cu1—O1—C3—C4	176.4 (2)	C16—C17—C18—C19	−0.7 (6)
Cu1—O1—C3—C2	−2.9 (5)	C16—C17—C18—Cl3	−179.8 (3)
C7—C2—C3—O1	−180.0 (3)	C17—C18—C19—C14	0.9 (6)
C1—C2—C3—O1	6.9 (5)	Cl3—C18—C19—C14	180.0 (3)
C7—C2—C3—C4	0.8 (5)	C15—C14—C19—C18	−0.3 (6)
C1—C2—C3—C4	−172.4 (3)	C13—C14—C19—C18	−176.5 (3)
O1—C3—C4—C5	−178.5 (3)	C24—N4—C20—C21	−1.3 (5)
C2—C3—C4—C5	0.8 (5)	C24—N4—C20—Cl4	178.3 (3)
C3—C4—C5—C6	−1.2 (6)	N4—C20—C21—C22	1.5 (5)
C4—C5—C6—C7	−0.1 (6)	Cl4—C20—C21—C22	−178.0 (3)
C4—C5—C6—Cl1	179.1 (3)	N4—C20—C21—N3	−173.4 (3)
C5—C6—C7—C2	1.7 (5)	Cl4—C20—C21—N3	7.1 (4)
Cl1—C6—C7—C2	−177.5 (3)	C13—N3—C21—C22	75.5 (4)
C3—C2—C7—C6	−2.0 (5)	Cu1—N3—C21—C22	−104.8 (3)
C1—C2—C7—C6	171.6 (3)	C13—N3—C21—C20	−109.9 (4)
C12—N2—C8—C9	−0.1 (6)	Cu1—N3—C21—C20	69.8 (4)
C12—N2—C8—Cl2	178.5 (3)	C20—C21—C22—C23	−0.1 (5)
N2—C8—C9—C10	−0.3 (6)	N3—C21—C22—C23	174.8 (3)
Cl2—C8—C9—C10	−178.9 (3)	C21—C22—C23—C24	−1.3 (5)
N2—C8—C9—N1	−178.4 (3)	C20—N4—C24—C23	−0.4 (6)
Cl2—C8—C9—N1	3.0 (4)	C22—C23—C24—N4	1.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···Cg1ⁱ	0.93	2.89	3.753 (3)	155

Symmetry code: (i) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₂H₇Cl₂N₂O)₂]
M_r	595.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	20.236 (2), 11.4821 (14), 10.5458 (9)
β (°)	90.132 (2)
V (Å³)	2450.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.36
Crystal size (mm)	0.40 × 0.14 × 0.09

Data collection
Diffractometer	Buker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.613, 0.888
No. of measured, independent and observed [I > 2σ(I)] reflections	12294, 4320, 2614
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.065, 1.02
No. of reflections	4320
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.39

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22···Cg1ⁱ	0.93	2.889	3.753 (3)	154.93

Symmetry code: (i) x, −y+3/2, z+1/2.

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0904-11) and the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University, which are gratefully acknowledged.

References

Abd El-Wahab, Z. H., Mashaly, M. M., Salman, A. A., El-Shetary, B. A. & Faheim, A. A. (2004). Spectrochim. Acta Part A, 60, 2861–2873. Google Scholar
Dong, W.-K., Tong, J.-F., An, L.-L., Wu, J.-C. & Yao, J. (2009c). Acta Cryst. E65, m945. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dong, W.-K., Wu, J.-C., Yao, J., Gong, S.-S. & Tong, J.-F. (2009a). Acta Cryst. E65, m802. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dong, W.-K., Wu, J.-C., Yao, J., Gong, S.-S. & Tong, J.-F. (2009b). Acta Cryst. E65, m803. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dong, W. K., Zhao, C. Y., Sun, Y. X., Tang, X. L. & He, X. N. (2009d). Inorg. Chem. Commun. 12, 234–236. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Soliman, A. A. & Mohamed, G. G. (2004). Thermochim. Acta, 421, 151–159. Web of Science CrossRef CAS Google Scholar

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Volume 65| Part 8| August 2009| Page m1013

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

Bis{(E)-4-chloro-2-[(2-chloro-3-pyrid­yl)imino­methyl-κN]phenolato-κO}copper(II)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis{(E)-4-chloro-2-[(2-chloro-3-pyridyl)iminomethyl-κN]phenolato-κO}copper(II)