Bis{2,4-dichloro-6-[3-(dimethyl­amino)propyl­imino­meth­yl]phenolato}copper(II)

Huang, X.-F.

doi:10.1107/S1600536809038045

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page m1246

doi:10.1107/S1600536809038045

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Bis{2,4-dichloro-6-[3-(dimethylamino)propyliminomethyl]phenolato}copper(II)

Xian-Feng Huang ^a ^*

^aSchool of Chemical Engineering, Jiangsu Polytechnic University, Changzhou 213164, People's Republic of China
^*Correspondence e-mail: huangxf007@gmail.com

(Received 18 September 2009; accepted 20 September 2009; online 26 September 2009)

In the title complex, [Cu(C₁₂H₁₅Cl₂N₂O)₂], the Cu^II ion is coordinated by one N,O-bidentate and one N,N′,O-tridentate Schiff base ligand, resulting in a distorted CuN₃O₂ square-based pyramidal coordination for the metal ion, with the O atoms lying trans to each other in the basal plane.

Related literature

For background on Schiff bases, see: Shi et al. (2007 , 2008 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Cu(C₁₂H₁₅Cl₂N₂O)₂]
M_r = 611.86
Triclinic, $[P \overline 1]$
a = 9.4099 (17) Å
b = 12.548 (2) Å
c = 12.603 (2) Å
α = 103.271 (7)°
β = 110.907 (7)°
γ = 90.614 (8)°
V = 1346.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.24 mm⁻¹
T = 296 K
0.28 × 0.24 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.723, T_max = 0.836
7433 measured reflections
5221 independent reflections
3718 reflections with I > 2σ(I)
R_int = 0.022
200 standard reflections every 3 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.112
S = 1.03
5221 reflections
320 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.63 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O2	1.921 (2)
Cu1—O1	1.924 (2)
Cu1—N1	2.003 (2)
Cu1—N3	2.009 (2)
Cu1—N2	2.459 (3)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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/S1600536809038045/hb5109sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809038045/hb5109Isup2.hkl

checkCIF report

Comment top

There has been much research interest in Schiff base metal complexes due to their molecular architectures and biological activities (Shi et al., 2007; Shi et al., 2008). In this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The Cu^II is coordinated by two O and three N atoms from the two Schiff base ligands, forming a distorted square-pyramidal coordination (Table 1).

Related literature top

For background on Schiff bases, see: Shi et al. (2007, 2008). For reference structural data, see: Allen et al. (1987).

Experimental top

A mixture of 3,5-dichloro-2-hydroxybenzaldehyde (380 mg, 2 mmol), N,N-dimethylpropane-1,3-diamine (204 mg, 2 mmol) and CuCl₂.4H₂O (1 mmol, 169 mg) was stirred in methanol (10 ml) for 1 h. After keeping the filtrate in air for 8 d, green block-shaped crystals of (I) were formed.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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 30% probability displacement ellipsoids.

Bis{2,4-dichloro-6-[3-(dimethylamino)propyliminomethyl]phenolato}copper(II) top

Crystal data top

[Cu(C₁₂H₁₅Cl₂N₂O)₂]	Z = 2
M_r = 611.86	F(000) = 630
Triclinic, P1	D_x = 1.510 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4099 (17) Å	Cell parameters from 25 reflections
b = 12.548 (2) Å	θ = 9–12°
c = 12.603 (2) Å	µ = 1.24 mm⁻¹
α = 103.271 (7)°	T = 296 K
β = 110.907 (7)°	Block, green
γ = 90.614 (8)°	0.28 × 0.24 × 0.15 mm
V = 1346.0 (4) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	3718 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.022
Graphite monochromator	θ_max = 26.0°, θ_min = 1.7°
ω/2θ scans	h = −11→9
Absorption correction: ψ scan (North et al., 1968)	k = −15→15
T_min = 0.723, T_max = 0.836	l = −15→15
7433 measured reflections	200 standard reflections every 3 reflections
5221 independent reflections	intensity decay: 1%

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0569P)² + 0.2468P] where P = (F_o² + 2F_c²)/3
5221 reflections	(Δ/σ)_max < 0.001
320 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Cu(C₁₂H₁₅Cl₂N₂O)₂]	γ = 90.614 (8)°
M_r = 611.86	V = 1346.0 (4) Å³
Triclinic, P1	Z = 2
a = 9.4099 (17) Å	Mo Kα radiation
b = 12.548 (2) Å	µ = 1.24 mm⁻¹
c = 12.603 (2) Å	T = 296 K
α = 103.271 (7)°	0.28 × 0.24 × 0.15 mm
β = 110.907 (7)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	3718 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.022
T_min = 0.723, T_max = 0.836	200 standard reflections every 3 reflections
7433 measured reflections	intensity decay: 1%
5221 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	Δρ_max = 0.39 e Å⁻³
5221 reflections	Δρ_min = −0.63 e Å⁻³
320 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
C1	1.0980 (3)	0.3757 (3)	0.4415 (3)	0.0422 (8)
C2	0.9891 (3)	0.2919 (3)	0.4160 (3)	0.0413 (7)
H2	1.0083	0.2402	0.4606	0.050*
C3	0.8480 (3)	0.2824 (2)	0.3233 (3)	0.0370 (7)
C4	0.8149 (3)	0.3598 (2)	0.2532 (3)	0.0333 (6)
C5	0.9332 (3)	0.4456 (2)	0.2853 (3)	0.0368 (7)
C6	1.0705 (3)	0.4550 (3)	0.3772 (3)	0.0419 (8)
H6	1.1440	0.5135	0.3961	0.050*
C7	0.7331 (4)	0.1966 (3)	0.3072 (3)	0.0412 (7)
H7	0.7569	0.1558	0.3632	0.049*
C8	0.4966 (4)	0.0924 (3)	0.2371 (3)	0.0522 (9)
H8A	0.5532	0.0519	0.2930	0.063*
H8B	0.4442	0.0400	0.1623	0.063*
C9	0.3798 (4)	0.1536 (3)	0.2794 (3)	0.0659 (11)
H9A	0.3207	0.1011	0.2971	0.079*
H9B	0.4353	0.2075	0.3524	0.079*
C10	0.2686 (4)	0.2124 (3)	0.1978 (3)	0.0548 (9)
H10A	0.2111	0.1587	0.1251	0.066*
H10B	0.1966	0.2420	0.2332	0.066*
C11	0.4186 (5)	0.3915 (3)	0.2752 (3)	0.0642 (11)
H11A	0.4538	0.4524	0.2536	0.096*
H11B	0.5045	0.3644	0.3266	0.096*
H11C	0.3499	0.4154	0.3147	0.096*
C12	0.2181 (4)	0.3478 (3)	0.0858 (4)	0.0632 (11)
H12A	0.1488	0.3794	0.1217	0.095*
H12B	0.1634	0.2898	0.0177	0.095*
H12C	0.2630	0.4035	0.0630	0.095*
C13	0.2720 (3)	0.0918 (2)	−0.0966 (3)	0.0333 (6)
C14	0.1557 (3)	0.0043 (2)	−0.1296 (3)	0.0383 (7)
C15	0.0300 (4)	−0.0163 (3)	−0.2318 (3)	0.0428 (8)
H15	−0.0437	−0.0744	−0.2497	0.051*
C16	0.0141 (3)	0.0509 (3)	−0.3084 (3)	0.0433 (8)
C17	0.1206 (3)	0.1374 (3)	−0.2816 (3)	0.0404 (7)
H17	0.1079	0.1819	−0.3333	0.048*
C18	0.2487 (3)	0.1596 (2)	−0.1769 (3)	0.0349 (7)
C19	0.3603 (3)	0.2499 (2)	−0.1558 (3)	0.0354 (7)
H19	0.3448	0.2842	−0.2165	0.042*
C20	0.5819 (3)	0.3732 (2)	−0.0704 (3)	0.0369 (7)
H20A	0.6133	0.4327	0.0004	0.044*
H20B	0.5278	0.4034	−0.1363	0.044*
C21	0.7230 (3)	0.3241 (3)	−0.0862 (3)	0.0425 (8)
H21A	0.7862	0.3808	−0.0946	0.051*
H21B	0.7821	0.3016	−0.0159	0.051*
C22	0.6870 (4)	0.2265 (3)	−0.1906 (3)	0.0446 (8)
H22A	0.7819	0.2025	−0.1970	0.054*
H22B	0.6344	0.1664	−0.1782	0.054*
C23	0.5059 (5)	0.1530 (3)	−0.3886 (3)	0.0611 (10)
H23A	0.4440	0.1730	−0.4588	0.092*
H23B	0.4413	0.1185	−0.3593	0.092*
H23C	0.5756	0.1028	−0.4057	0.092*
C24	0.6815 (5)	0.3107 (3)	−0.3461 (3)	0.0604 (10)
H24A	0.7537	0.2646	−0.3658	0.091*
H24B	0.7353	0.3763	−0.2877	0.091*
H24C	0.6145	0.3303	−0.4150	0.091*
Cl1	0.90023 (10)	0.54424 (7)	0.20416 (9)	0.0563 (2)
Cl2	1.27444 (10)	0.38562 (9)	0.55552 (8)	0.0654 (3)
Cl3	0.17577 (11)	−0.08122 (7)	−0.03566 (8)	0.0597 (3)
Cl4	−0.14445 (10)	0.02090 (9)	−0.43971 (8)	0.0639 (3)
Cu1	0.52922 (4)	0.23541 (3)	0.08518 (3)	0.03432 (13)
N1	0.6029 (3)	0.1709 (2)	0.2244 (2)	0.0400 (6)
N2	0.3386 (3)	0.3034 (2)	0.1693 (2)	0.0460 (7)
N3	0.4784 (3)	0.28772 (18)	−0.0621 (2)	0.0331 (6)
N4	0.5920 (3)	0.2517 (2)	−0.3004 (2)	0.0414 (6)
O1	0.6871 (2)	0.35606 (17)	0.16617 (18)	0.0401 (5)
O2	0.3892 (2)	0.10554 (16)	−0.00087 (18)	0.0400 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0273 (16)	0.054 (2)	0.0371 (18)	0.0020 (15)	0.0087 (13)	0.0013 (15)
C2	0.0361 (18)	0.050 (2)	0.0334 (17)	0.0031 (15)	0.0078 (14)	0.0107 (15)
C3	0.0327 (16)	0.0389 (17)	0.0369 (17)	−0.0020 (13)	0.0119 (14)	0.0066 (14)
C4	0.0299 (16)	0.0358 (16)	0.0343 (16)	0.0006 (13)	0.0136 (13)	0.0064 (13)
C5	0.0307 (16)	0.0373 (17)	0.0426 (18)	−0.0012 (13)	0.0160 (14)	0.0064 (14)
C6	0.0256 (16)	0.0432 (18)	0.051 (2)	−0.0064 (14)	0.0155 (15)	−0.0016 (15)
C7	0.0425 (19)	0.0410 (18)	0.0408 (18)	0.0001 (15)	0.0109 (15)	0.0191 (15)
C8	0.051 (2)	0.050 (2)	0.054 (2)	−0.0174 (17)	0.0076 (17)	0.0292 (17)
C9	0.064 (3)	0.083 (3)	0.057 (2)	−0.025 (2)	0.025 (2)	0.027 (2)
C10	0.048 (2)	0.057 (2)	0.068 (2)	−0.0110 (17)	0.0346 (19)	0.0102 (19)
C11	0.070 (3)	0.056 (2)	0.069 (3)	−0.011 (2)	0.043 (2)	−0.007 (2)
C12	0.051 (2)	0.065 (3)	0.084 (3)	0.014 (2)	0.034 (2)	0.024 (2)
C13	0.0286 (16)	0.0334 (16)	0.0360 (17)	0.0000 (13)	0.0120 (13)	0.0053 (13)
C14	0.0353 (17)	0.0332 (16)	0.0457 (19)	−0.0014 (13)	0.0150 (15)	0.0089 (14)
C15	0.0328 (17)	0.0397 (18)	0.052 (2)	−0.0060 (14)	0.0172 (15)	0.0025 (15)
C16	0.0276 (16)	0.054 (2)	0.0412 (19)	0.0013 (15)	0.0101 (14)	0.0022 (15)
C17	0.0324 (17)	0.0500 (19)	0.0388 (18)	0.0007 (14)	0.0128 (14)	0.0121 (15)
C18	0.0293 (16)	0.0393 (17)	0.0369 (17)	0.0005 (13)	0.0132 (13)	0.0093 (14)
C19	0.0325 (16)	0.0386 (17)	0.0381 (17)	0.0011 (13)	0.0145 (14)	0.0132 (14)
C20	0.0403 (17)	0.0333 (16)	0.0357 (17)	−0.0091 (13)	0.0118 (14)	0.0103 (13)
C21	0.0342 (17)	0.0462 (19)	0.0477 (19)	−0.0060 (14)	0.0139 (15)	0.0153 (16)
C22	0.0420 (19)	0.0457 (19)	0.053 (2)	0.0043 (15)	0.0236 (16)	0.0166 (16)
C23	0.069 (3)	0.055 (2)	0.057 (2)	−0.0106 (19)	0.026 (2)	0.0059 (19)
C24	0.071 (3)	0.058 (2)	0.063 (2)	−0.0083 (19)	0.035 (2)	0.0188 (19)
Cl1	0.0476 (5)	0.0483 (5)	0.0710 (6)	−0.0102 (4)	0.0140 (4)	0.0243 (4)
Cl2	0.0340 (5)	0.0921 (8)	0.0524 (6)	−0.0029 (5)	−0.0006 (4)	0.0117 (5)
Cl3	0.0596 (6)	0.0484 (5)	0.0653 (6)	−0.0160 (4)	0.0104 (5)	0.0245 (5)
Cl4	0.0360 (5)	0.0847 (7)	0.0519 (6)	−0.0094 (5)	−0.0006 (4)	0.0083 (5)
Cu1	0.0302 (2)	0.0355 (2)	0.0352 (2)	−0.00629 (15)	0.00768 (16)	0.01242 (16)
N1	0.0374 (15)	0.0360 (14)	0.0452 (16)	−0.0081 (11)	0.0110 (13)	0.0148 (12)
N2	0.0462 (16)	0.0438 (16)	0.0524 (17)	−0.0043 (13)	0.0258 (14)	0.0084 (13)
N3	0.0291 (13)	0.0331 (14)	0.0389 (15)	−0.0021 (11)	0.0132 (12)	0.0117 (11)
N4	0.0418 (15)	0.0427 (15)	0.0434 (16)	−0.0038 (12)	0.0200 (13)	0.0111 (12)
O1	0.0332 (12)	0.0422 (12)	0.0407 (12)	−0.0090 (9)	0.0055 (10)	0.0162 (10)
O2	0.0380 (12)	0.0374 (12)	0.0393 (12)	−0.0055 (9)	0.0054 (10)	0.0142 (10)

Geometric parameters (Å, º) top

C1—C2	1.359 (4)	C14—C15	1.370 (4)
C1—C6	1.393 (4)	C14—Cl3	1.737 (3)
C1—Cl2	1.745 (3)	C15—C16	1.393 (4)
C2—C3	1.403 (4)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.365 (4)
C3—C4	1.423 (4)	C16—Cl4	1.745 (3)
C3—C7	1.445 (4)	C17—C18	1.401 (4)
C4—O1	1.298 (3)	C17—H17	0.9300
C4—C5	1.419 (4)	C18—C19	1.446 (4)
C5—C6	1.375 (4)	C19—N3	1.284 (4)
C5—Cl1	1.743 (3)	C19—H19	0.9300
C6—H6	0.9300	C20—N3	1.488 (3)
C7—N1	1.272 (4)	C20—C21	1.527 (4)
C7—H7	0.9300	C20—H20A	0.9700
C8—N1	1.470 (3)	C20—H20B	0.9700
C8—C9	1.527 (5)	C21—C22	1.510 (4)
C8—H8A	0.9700	C21—H21A	0.9700
C8—H8B	0.9700	C21—H21B	0.9700
C9—C10	1.514 (5)	C22—N4	1.461 (4)
C9—H9A	0.9700	C22—H22A	0.9700
C9—H9B	0.9700	C22—H22B	0.9700
C10—N2	1.485 (4)	C23—N4	1.459 (4)
C10—H10A	0.9700	C23—H23A	0.9600
C10—H10B	0.9700	C23—H23B	0.9600
C11—N2	1.470 (4)	C23—H23C	0.9600
C11—H11A	0.9600	C24—N4	1.456 (4)
C11—H11B	0.9600	C24—H24A	0.9600
C11—H11C	0.9600	C24—H24B	0.9600
C12—N2	1.462 (4)	C24—H24C	0.9600
C12—H12A	0.9600	Cu1—O2	1.921 (2)
C12—H12B	0.9600	Cu1—O1	1.924 (2)
C12—H12C	0.9600	Cu1—N1	2.003 (2)
C13—O2	1.285 (3)	Cu1—N3	2.009 (2)
C13—C14	1.421 (4)	Cu1—N2	2.459 (3)
C13—C18	1.427 (4)

C2—C1—C6	120.5 (3)	C18—C17—H17	119.7
C2—C1—Cl2	120.5 (3)	C17—C18—C13	120.9 (3)
C6—C1—Cl2	119.0 (2)	C17—C18—C19	117.9 (3)
C1—C2—C3	120.7 (3)	C13—C18—C19	121.2 (3)
C1—C2—H2	119.6	N3—C19—C18	126.9 (3)
C3—C2—H2	119.6	N3—C19—H19	116.5
C2—C3—C4	121.1 (3)	C18—C19—H19	116.5
C2—C3—C7	117.7 (3)	N3—C20—C21	110.5 (2)
C4—C3—C7	121.0 (3)	N3—C20—H20A	109.5
O1—C4—C5	120.5 (3)	C21—C20—H20A	109.5
O1—C4—C3	124.4 (3)	N3—C20—H20B	109.5
C5—C4—C3	115.1 (3)	C21—C20—H20B	109.5
C6—C5—C4	123.4 (3)	H20A—C20—H20B	108.1
C6—C5—Cl1	118.8 (2)	C22—C21—C20	114.1 (3)
C4—C5—Cl1	117.7 (2)	C22—C21—H21A	108.7
C5—C6—C1	119.0 (3)	C20—C21—H21A	108.7
C5—C6—H6	120.5	C22—C21—H21B	108.7
C1—C6—H6	120.5	C20—C21—H21B	108.7
N1—C7—C3	126.8 (3)	H21A—C21—H21B	107.6
N1—C7—H7	116.6	N4—C22—C21	112.6 (3)
C3—C7—H7	116.6	N4—C22—H22A	109.1
N1—C8—C9	110.1 (3)	C21—C22—H22A	109.1
N1—C8—H8A	109.6	N4—C22—H22B	109.1
C9—C8—H8A	109.6	C21—C22—H22B	109.1
N1—C8—H8B	109.6	H22A—C22—H22B	107.8
C9—C8—H8B	109.6	N4—C23—H23A	109.5
H8A—C8—H8B	108.2	N4—C23—H23B	109.5
C10—C9—C8	117.6 (3)	H23A—C23—H23B	109.5
C10—C9—H9A	107.9	N4—C23—H23C	109.5
C8—C9—H9A	107.9	H23A—C23—H23C	109.5
C10—C9—H9B	107.9	H23B—C23—H23C	109.5
C8—C9—H9B	107.9	N4—C24—H24A	109.5
H9A—C9—H9B	107.2	N4—C24—H24B	109.5
N2—C10—C9	115.5 (3)	H24A—C24—H24B	109.5
N2—C10—H10A	108.4	N4—C24—H24C	109.5
C9—C10—H10A	108.4	H24A—C24—H24C	109.5
N2—C10—H10B	108.4	H24B—C24—H24C	109.5
C9—C10—H10B	108.4	O2—Cu1—O1	173.30 (9)
H10A—C10—H10B	107.5	O2—Cu1—N1	89.22 (9)
N2—C11—H11A	109.5	O1—Cu1—N1	90.08 (9)
N2—C11—H11B	109.5	O2—Cu1—N3	90.21 (9)
H11A—C11—H11B	109.5	O1—Cu1—N3	89.49 (9)
N2—C11—H11C	109.5	N1—Cu1—N3	171.46 (10)
H11A—C11—H11C	109.5	O2—Cu1—N2	87.36 (9)
H11B—C11—H11C	109.5	O1—Cu1—N2	99.17 (9)
N2—C12—H12A	109.5	N1—Cu1—N2	82.79 (10)
N2—C12—H12B	109.5	N3—Cu1—N2	105.69 (9)
H12A—C12—H12B	109.5	C7—N1—C8	116.5 (3)
N2—C12—H12C	109.5	C7—N1—Cu1	125.1 (2)
H12A—C12—H12C	109.5	C8—N1—Cu1	118.3 (2)
H12B—C12—H12C	109.5	C12—N2—C11	109.4 (3)
O2—C13—C14	120.6 (3)	C12—N2—C10	108.9 (3)
O2—C13—C18	124.1 (3)	C11—N2—C10	111.1 (3)
C14—C13—C18	115.3 (3)	C12—N2—Cu1	110.2 (2)
C15—C14—C13	123.3 (3)	C11—N2—Cu1	107.1 (2)
C15—C14—Cl3	118.8 (2)	C10—N2—Cu1	110.2 (2)
C13—C14—Cl3	117.9 (2)	C19—N3—C20	114.8 (2)
C14—C15—C16	119.1 (3)	C19—N3—Cu1	124.33 (19)
C14—C15—H15	120.4	C20—N3—Cu1	120.80 (18)
C16—C15—H15	120.4	C24—N4—C23	110.6 (3)
C17—C16—C15	120.7 (3)	C24—N4—C22	111.8 (3)
C17—C16—Cl4	121.0 (3)	C23—N4—C22	111.9 (3)
C15—C16—Cl4	118.3 (2)	C4—O1—Cu1	128.22 (18)
C16—C17—C18	120.6 (3)	C13—O2—Cu1	128.34 (18)
C16—C17—H17	119.7

Experimental details

Crystal data
Chemical formula	[Cu(C₁₂H₁₅Cl₂N₂O)₂]
M_r	611.86
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.4099 (17), 12.548 (2), 12.603 (2)
α, β, γ (°)	103.271 (7), 110.907 (7), 90.614 (8)
V (Å³)	1346.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.24
Crystal size (mm)	0.28 × 0.24 × 0.15

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.723, 0.836
No. of measured, independent and observed [I > 2σ(I)] reflections	7433, 5221, 3718
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.112, 1.03
No. of reflections	5221
No. of parameters	320
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.63

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—O2	1.921 (2)	Cu1—N3	2.009 (2)
Cu1—O1	1.924 (2)	Cu1—N2	2.459 (3)
Cu1—N1	2.003 (2)

Acknowledgements

The work was supported by the Doctoral Fund (Project ZMF 08020066) of Jiangsu Polytechnic University.

References

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