{2-[(3,5-Dichloro-2-oxidobenzyl­idene)amino-κ2N,O]-3-methyl­penta­noato-κO}(N,N′-dimethyl­formamide-κO)copper(II)

Xia, J.H.; Liu, Z.; Wang, Y.; Feng, X.Z.

doi:10.1107/S160053680800932X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages m660-m661

doi:10.1107/S160053680800932X

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{2-[(3,5-Dichloro-2-oxidobenzylidene)amino-κ²N,O]-3-methylpentanoato-κO}(N,N′-dimethylformamide-κO)copper(II)

Jin Hong Xia,^a Zheng Liu,^b Yuan Wang ^b and Xiao Zhen Feng ^b ^*

^aCollege of Electronic Engineering, Guilin University of Electronic Technology, Ministry of Education, Guangxi, Guilin 541004, People's Republic of China, and ^bKey Laboratory of Non-ferrous Metal Materials and Processing Technology, Department of Materials and Chemical Engineering, Guilin University of Technology, Ministry of Education, Guilin 541004, People's Republic of China
^*Correspondence e-mail: lisa4.6@163.com

(Received 8 January 2008; accepted 6 April 2008; online 16 April 2008)

In the title compound, [Cu(C₁₃H₁₃Cl₂NO₃)(C₃H₇NO)], the Cu^II atom is coordinated in a slightly distorted square-planar geometry by two O atoms and one N atom from the tridentate chiral ligand 2-[(3,5-dichloro-2-oxidobenzylidene)amino]-3-methylpentanoate and by one O atom from dimethylformamide. In the crystal structure, the Cu atom forms contacts with Cl and O atoms of two units (Cu⋯Cl and Cu⋯O = 3.401 and 2.947 Å, respectively), thereby forming an approximately octahedral arrangement. A three-dimensional network is constructed through Cl⋯Cu, O⋯Cu, Cl⋯Cl contacts and C—H⋯O hydrogen bonds.

Related literature

For Schiff base complexes containing amino acids, see: Garcia-Raso et al. (1996 ); Dawes et al. (1982 ); Laurent et al. (1982 ); Zhang et al. (2006 ). For related literature, see: Cohen et al. (1964 ); Garcia-Orozco et al. (2002 ); Hu & Englert (2006 ); Royles & Sherrington (2000 ); Subramanian et al. (2000 ); Zaman et al. (2004 ); Zordan et al. (2005 ).

Experimental

Crystal data

[Cu(C₁₃H₁₃Cl₂NO₃)(C₃H₇NO)]
M_r = 438.78
Orthorhombic, P 2₁ 2₁ 2
a = 11.671 (2) Å
b = 27.465 (3) Å
c = 5.8890 (18) Å
V = 1887.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.46 mm⁻¹
T = 298 (2) K
0.43 × 0.15 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.572, T_max = 0.833
9274 measured reflections
3260 independent reflections
2288 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.095
wR(F²) = 0.242
S = 1.05
3260 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −1.08 e Å⁻³
Absolute structure: Flack (1983 ), with 1915 Friedel pairs
Flack parameter: 0.11 (6)

Table 1
Selected geometric parameters (Å, °)

Cu1—O3	1.872 (9)
Cu1—O1	1.905 (9)
Cu1—O4	1.920 (9)
Cu1—N1	1.925 (10)

O3—Cu1—O1	169.2 (4)
O3—Cu1—O4	92.5 (4)
O1—Cu1—O4	90.5 (3)
O3—Cu1—N1	94.2 (4)
O1—Cu1—N1	82.7 (4)
O4—Cu1—N1	173.1 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯O2ⁱ	0.96	2.31	3.19 (2)	150
Symmetry code: (i) -x, -y+2, z-1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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/S160053680800932X/gw2039sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800932X/gw2039Isup2.hkl

checkCIF report

Comment top

Schiff bases is a kind of very important compounds in coordination chemistry. And Schiff base complexes have been increasing interest because of their antivial,anticancer and antibacterial activities.Just as the title compound, it's amino acid salicylicaldehyde of halogen substituent Schiff base. Meanwhile,we find some unusual bonds which look like hydrogen bond in this halogenated compound.

In (I),the Cu^II atom is coordinated by two O atoms, one N atom, which come from one tridentate ligand 2-[(3,5-dichloro-2-oxidobenzylidene)amino]-3-methylpentanoate and one O atom from N,N-Dimethyl-formamide, forming a slightly distorted planar square geometry (Fig. 1). In the unit one-dimensional chains, the distorted planar square with Cl and O which above or below of it form an approximately "octahedral". The weak interaction length of Cl–Cu and O–Cu is 3.401 Å. and 2.947 Å. These can be seen the reasults of Jahn-Teller effect. (Garcia-Orozco et al., 2002) People have interest in packing arrangements of halogenated compounds date back to what Schmidt called the 'chloro effect', where the presence of chloro substituents on aromatic compounds frequently arise from stacking arrangements with a short (ca 4 Å) crystallographic axis (Cohen et al., 1964; Zaman et al., 2004; Zordan et al., 2005). The title compound contains the dichloride ligand 2-[(3,5-dichloro-2-oxidobenzylidene)amino]-3-methylpentanoate, with two Cl atoms accessible at the periphery of the ligand. The three-dimensional network of (I) through short Cl–Cu, Cl–Cl, O–Cu contacts and C–H···O hydrogen bonds.(Fig.3). The weak interaction length of Cl–Cl is 3.349 Å. The final position parameters of the nonhydrogen atoms are given in Table 1. The selected bond lengths and bond angles are listed in Table 2.

Related literature top

For Schiff base complexes containing amino acids, see: Garcia-Raso et al. (1996); Dawes et al. (1982); Laurent et al. (1982); Zhang et al. (2006). For related literature, see: Cohen et al. (1964); Garcia-Orozco, Tapia-Benavides & Alvarez-Toledano (2002); Hu & Ulli Englert (2006); Royles & Sherrington (2000); Subramanian et al. (2000); Zaman et al. (2004); Zordan et al. (2005).

Experimental top

The title compound was produced from aqueous solution of copper chloride and A ethanol solution of (E)-2-(3,5-dichloro-2-hydroxybenzylideneamino)-3 -methylpentanoic acid with vapour volatilization of N,N-Dimethyl-formamide at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 asymmetric unit of (I), showing 30% probability displacement ellipsoids. Carbon-bound H atoms have been omitted.
	Fig. 2. The interactions of Cl···Cu and O···Cu in the asymmetric unit one-dimensional chains.
	Fig. 3. Three-dimensional network of (I), broken line showing Short Cl–Cl, Cl···Cu and O···Cu contacts, C–H···O hydrogen bonds.

{2-[(3,5-Dichloro-2-oxidobenzylidene)amino-κ²N,O]-3-methylpentanoato- κO}(N,N'-dimethylformamide-κO)copper(II) top

Crystal data top

[Cu(C₁₃H₁₃Cl₂NO₃)(C₃H₇NO)]	D_x = 1.544 Mg m⁻³
M_r = 438.78	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2	Cell parameters from 1991 reflections
a = 11.671 (2) Å	θ = 2.3–20.3°
b = 27.465 (3) Å	µ = 1.46 mm⁻¹
c = 5.8890 (18) Å	T = 298 K
V = 1887.7 (7) Å³	Block, blue
Z = 4	0.43 × 0.15 × 0.13 mm
F(000) = 900

Data collection top

Bruker SMART CCD area-detector diffractometer	3260 independent reflections
Radiation source: fine-focus sealed tube	2288 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.087
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→13
T_min = 0.572, T_max = 0.833	k = −32→32
9274 measured reflections	l = −6→6

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)] = 0.095	H-atom parameters constrained
wR(F²) = 0.242	w = 1/[σ²(F_o²) + (0.1179P)² + 7.0901P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3260 reflections	Δρ_max = 0.54 e Å⁻³
226 parameters	Δρ_min = −1.08 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1310 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.11 (6)

Crystal data top

[Cu(C₁₃H₁₃Cl₂NO₃)(C₃H₇NO)]	V = 1887.7 (7) Å³
M_r = 438.78	Z = 4
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 11.671 (2) Å	µ = 1.46 mm⁻¹
b = 27.465 (3) Å	T = 298 K
c = 5.8890 (18) Å	0.43 × 0.15 × 0.13 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3260 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2288 reflections with I > 2σ(I)
T_min = 0.572, T_max = 0.833	R_int = 0.087
9274 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.095	H-atom parameters constrained
wR(F²) = 0.242	Δρ_max = 0.54 e Å⁻³
S = 1.05	Δρ_min = −1.08 e Å⁻³
3260 reflections	Absolute structure: Flack (1983), 1310 Friedel pairs
226 parameters	Absolute structure parameter: 0.11 (6)
0 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	0.13255 (12)	0.88233 (5)	0.7191 (3)	0.0369 (4)
Cl1	0.0068 (3)	0.79870 (13)	0.0644 (6)	0.0481 (9)
Cl2	0.2946 (3)	0.65124 (12)	0.2389 (8)	0.0671 (12)
N1	0.2606 (8)	0.8445 (3)	0.8257 (17)	0.033 (2)
N2	−0.1115 (10)	0.9551 (4)	0.3728 (17)	0.043 (3)
O1	0.1585 (7)	0.9174 (3)	0.9935 (17)	0.046 (2)
O2	0.2565 (10)	0.9193 (4)	1.3185 (19)	0.063 (3)
O3	0.0957 (7)	0.8388 (3)	0.4856 (18)	0.044 (2)
O4	0.0063 (7)	0.9243 (3)	0.6463 (15)	0.039 (2)
C1	0.2446 (12)	0.9026 (5)	1.125 (2)	0.038 (3)
C2	0.3198 (12)	0.8638 (4)	1.029 (2)	0.035 (3)
H2	0.3294	0.8377	1.1411	0.042*
C3	0.4373 (11)	0.8833 (7)	0.960 (3)	0.059 (4)
H3	0.4762	0.8584	0.8687	0.071*
C4	0.5115 (15)	0.8947 (7)	1.168 (3)	0.067 (5)
H4A	0.5874	0.9039	1.1162	0.080*
H4B	0.4789	0.9226	1.2457	0.080*
C5	0.5232 (16)	0.8529 (7)	1.338 (3)	0.077 (5)
H5A	0.4651	0.8559	1.4523	0.115*
H5B	0.5974	0.8542	1.4076	0.115*
H5C	0.5145	0.8224	1.2600	0.115*
C6	0.4285 (13)	0.9300 (7)	0.818 (3)	0.077 (6)
H6A	0.3701	0.9261	0.7044	0.116*
H6B	0.5007	0.9363	0.7453	0.116*
H6C	0.4092	0.9568	0.9150	0.116*
C7	0.2818 (10)	0.7995 (4)	0.755 (2)	0.040 (3)
H7	0.3322	0.7813	0.8426	0.047*
C8	0.2357 (11)	0.7757 (4)	0.557 (2)	0.034 (3)
C9	0.1437 (12)	0.7977 (4)	0.428 (2)	0.041 (3)
C10	0.1061 (8)	0.7732 (4)	0.235 (2)	0.031 (3)
C11	0.1625 (11)	0.7281 (4)	0.181 (2)	0.043 (3)
H11	0.1418	0.7123	0.0474	0.051*
C12	0.2427 (10)	0.7075 (5)	0.310 (3)	0.043 (3)
C13	0.2807 (11)	0.7309 (5)	0.495 (3)	0.044 (3)
H13	0.3380	0.7170	0.5836	0.053*
C14	−0.0233 (13)	0.9290 (4)	0.448 (3)	0.048 (4)
H14	0.0203	0.9128	0.3393	0.058*
C15	−0.1907 (13)	0.9786 (5)	0.540 (3)	0.053 (4)
H15A	−0.2402	0.9544	0.6047	0.080*
H15B	−0.2361	1.0028	0.4636	0.080*
H15C	−0.1467	0.9938	0.6579	0.080*
C16	−0.1495 (16)	0.9579 (7)	0.135 (3)	0.063 (5)
H16A	−0.0882	0.9478	0.0366	0.094*
H16B	−0.1709	0.9908	0.0995	0.094*
H16C	−0.2143	0.9368	0.1129	0.094*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0356 (7)	0.0313 (6)	0.0437 (9)	0.0098 (6)	−0.0076 (7)	−0.0074 (7)
Cl1	0.0389 (18)	0.061 (2)	0.044 (2)	−0.0044 (16)	−0.0118 (16)	0.0061 (17)
Cl2	0.081 (3)	0.0460 (18)	0.074 (3)	−0.0011 (17)	0.018 (3)	−0.019 (2)
N1	0.039 (5)	0.030 (5)	0.028 (6)	0.009 (4)	−0.013 (5)	−0.012 (4)
N2	0.044 (7)	0.055 (7)	0.030 (6)	0.032 (6)	0.002 (5)	0.011 (5)
O1	0.024 (5)	0.049 (5)	0.066 (7)	0.017 (4)	−0.021 (4)	−0.005 (5)
O2	0.069 (7)	0.066 (7)	0.055 (7)	0.012 (6)	−0.009 (6)	−0.021 (6)
O3	0.040 (5)	0.024 (4)	0.069 (7)	0.009 (4)	−0.012 (4)	−0.010 (4)
O4	0.026 (4)	0.060 (6)	0.031 (5)	0.004 (4)	0.004 (4)	−0.002 (4)
C1	0.032 (7)	0.042 (7)	0.041 (8)	−0.008 (6)	0.012 (6)	−0.014 (6)
C2	0.051 (8)	0.034 (6)	0.020 (6)	0.007 (5)	0.006 (6)	−0.004 (5)
C3	0.022 (7)	0.086 (11)	0.068 (10)	0.020 (8)	−0.006 (7)	−0.017 (11)
C4	0.054 (9)	0.091 (13)	0.056 (10)	−0.008 (9)	−0.011 (8)	−0.011 (9)
C5	0.063 (11)	0.091 (13)	0.076 (13)	0.003 (10)	−0.028 (10)	−0.010 (10)
C6	0.031 (8)	0.111 (14)	0.091 (14)	−0.005 (8)	0.008 (9)	−0.028 (13)
C7	0.040 (7)	0.049 (7)	0.031 (8)	0.014 (5)	0.001 (6)	−0.007 (7)
C8	0.040 (7)	0.032 (6)	0.030 (7)	0.002 (5)	−0.004 (6)	−0.002 (5)
C9	0.048 (8)	0.034 (6)	0.041 (8)	0.008 (6)	0.006 (7)	0.001 (6)
C10	0.022 (6)	0.043 (6)	0.029 (7)	0.001 (4)	0.004 (5)	0.012 (6)
C11	0.051 (8)	0.031 (6)	0.046 (9)	−0.021 (6)	−0.002 (7)	−0.004 (6)
C12	0.030 (6)	0.042 (7)	0.058 (9)	−0.006 (6)	0.016 (7)	−0.025 (7)
C13	0.026 (7)	0.039 (7)	0.067 (10)	0.000 (5)	0.005 (6)	−0.006 (7)
C14	0.059 (9)	0.029 (7)	0.056 (10)	0.015 (6)	0.005 (8)	0.013 (7)
C15	0.052 (9)	0.055 (8)	0.053 (10)	0.012 (7)	−0.008 (8)	−0.006 (7)
C16	0.059 (11)	0.081 (11)	0.048 (10)	0.004 (9)	0.015 (8)	−0.010 (8)

Geometric parameters (Å, º) top

Cu1—O3	1.872 (9)	C5—H5A	0.9600
Cu1—O1	1.905 (9)	C5—H5B	0.9600
Cu1—O4	1.920 (9)	C5—H5C	0.9600
Cu1—N1	1.925 (10)	C6—H6A	0.9600
Cl1—C10	1.685 (11)	C6—H6B	0.9600
Cl2—C12	1.712 (12)	C6—H6C	0.9600
N1—C7	1.328 (14)	C7—C8	1.442 (17)
N1—C2	1.482 (16)	C7—H7	0.9300
N2—C14	1.329 (17)	C8—C13	1.384 (16)
N2—C16	1.473 (19)	C8—C9	1.444 (17)
N2—C15	1.497 (18)	C9—C10	1.395 (17)
O1—C1	1.333 (17)	C10—C11	1.438 (17)
O2—C1	1.233 (16)	C11—C12	1.333 (19)
O3—C9	1.306 (14)	C11—H11	0.9300
O4—C14	1.225 (17)	C12—C13	1.341 (19)
C1—C2	1.493 (17)	C13—H13	0.9300
C2—C3	1.53 (2)	C14—H14	0.9300
C2—H2	0.9800	C15—H15A	0.9600
C3—C4	1.53 (2)	C15—H15B	0.9600
C3—C6	1.53 (3)	C15—H15C	0.9600
C3—H3	0.9800	C16—H16A	0.9600
C4—C5	1.53 (2)	C16—H16B	0.9600
C4—H4A	0.9700	C16—H16C	0.9600
C4—H4B	0.9700

O3—Cu1—O1	169.2 (4)	C3—C6—H6A	109.5
O3—Cu1—O4	92.5 (4)	C3—C6—H6B	109.5
O1—Cu1—O4	90.5 (3)	H6A—C6—H6B	109.5
O3—Cu1—N1	94.2 (4)	C3—C6—H6C	109.5
O1—Cu1—N1	82.7 (4)	H6A—C6—H6C	109.5
O4—Cu1—N1	173.1 (4)	H6B—C6—H6C	109.5
C7—N1—C2	120.0 (10)	N1—C7—C8	127.5 (11)
C7—N1—Cu1	122.9 (8)	N1—C7—H7	116.3
C2—N1—Cu1	115.7 (7)	C8—C7—H7	116.3
C14—N2—C16	125.3 (13)	C13—C8—C7	118.2 (11)
C14—N2—C15	119.5 (12)	C13—C8—C9	121.1 (12)
C16—N2—C15	114.6 (11)	C7—C8—C9	120.7 (10)
C1—O1—Cu1	117.4 (7)	O3—C9—C10	119.5 (11)
C9—O3—Cu1	130.0 (9)	O3—C9—C8	123.1 (11)
C14—O4—Cu1	119.5 (8)	C10—C9—C8	117.4 (10)
O2—C1—O1	120.6 (13)	C9—C10—C11	116.8 (10)
O2—C1—C2	123.3 (14)	C9—C10—Cl1	120.2 (9)
O1—C1—C2	116.1 (11)	C11—C10—Cl1	122.8 (10)
N1—C2—C1	106.7 (11)	C12—C11—C10	124.2 (12)
N1—C2—C3	109.0 (10)	C12—C11—H11	117.9
C1—C2—C3	112.3 (11)	C10—C11—H11	117.9
N1—C2—H2	109.6	C11—C12—C13	119.5 (12)
C1—C2—H2	109.6	C11—C12—Cl2	119.4 (11)
C3—C2—H2	109.6	C13—C12—Cl2	121.1 (12)
C2—C3—C4	111.3 (13)	C12—C13—C8	120.8 (13)
C2—C3—C6	112.3 (11)	C12—C13—H13	119.6
C4—C3—C6	107.6 (15)	C8—C13—H13	119.6
C2—C3—H3	108.5	O4—C14—N2	126.3 (14)
C4—C3—H3	108.5	O4—C14—H14	116.9
C6—C3—H3	108.5	N2—C14—H14	116.9
C5—C4—C3	114.9 (15)	N2—C15—H15A	109.5
C5—C4—H4A	108.5	N2—C15—H15B	109.5
C3—C4—H4A	108.5	H15A—C15—H15B	109.5
C5—C4—H4B	108.5	N2—C15—H15C	109.5
C3—C4—H4B	108.5	H15A—C15—H15C	109.5
H4A—C4—H4B	107.5	H15B—C15—H15C	109.5
C4—C5—H5A	109.5	N2—C16—H16A	109.5
C4—C5—H5B	109.5	N2—C16—H16B	109.5
H5A—C5—H5B	109.5	H16A—C16—H16B	109.5
C4—C5—H5C	109.5	N2—C16—H16C	109.5
H5A—C5—H5C	109.5	H16A—C16—H16C	109.5
H5B—C5—H5C	109.5	H16B—C16—H16C	109.5

O3—Cu1—N1—C7	−10.6 (11)	C6—C3—C4—C5	176.2 (14)
O1—Cu1—N1—C7	159.0 (11)	C2—N1—C7—C8	−177.5 (12)
O3—Cu1—N1—C2	−177.3 (8)	Cu1—N1—C7—C8	16.4 (19)
O1—Cu1—N1—C2	−7.7 (8)	N1—C7—C8—C13	171.3 (12)
O3—Cu1—O1—C1	74 (2)	N1—C7—C8—C9	−10 (2)
O4—Cu1—O1—C1	180.0 (9)	Cu1—O3—C9—C10	−175.0 (8)
N1—Cu1—O1—C1	0.4 (9)	Cu1—O3—C9—C8	4.8 (19)
O1—Cu1—O3—C9	−72 (2)	C13—C8—C9—O3	177.1 (12)
O4—Cu1—O3—C9	−177.7 (11)	C7—C8—C9—O3	−2 (2)
N1—Cu1—O3—C9	0.7 (12)	C13—C8—C9—C10	−3.1 (18)
O3—Cu1—O4—C14	−34.2 (11)	C7—C8—C9—C10	178.0 (11)
O1—Cu1—O4—C14	156.2 (11)	O3—C9—C10—C11	180.0 (11)
Cu1—O1—C1—O2	−170.2 (10)	C8—C9—C10—C11	0.1 (16)
Cu1—O1—C1—C2	7.0 (14)	O3—C9—C10—Cl1	4.9 (16)
C7—N1—C2—C1	−154.7 (12)	C8—C9—C10—Cl1	−175.0 (9)
Cu1—N1—C2—C1	12.4 (12)	C9—C10—C11—C12	3.9 (18)
C7—N1—C2—C3	83.7 (14)	Cl1—C10—C11—C12	178.8 (10)
Cu1—N1—C2—C3	−109.1 (11)	C10—C11—C12—C13	−5 (2)
O2—C1—C2—N1	164.9 (13)	C10—C11—C12—Cl2	174.6 (9)
O1—C1—C2—N1	−12.2 (15)	C11—C12—C13—C8	2 (2)
O2—C1—C2—C3	−75.7 (17)	Cl2—C12—C13—C8	−177.8 (10)
O1—C1—C2—C3	107.2 (13)	C7—C8—C13—C12	−178.7 (12)
N1—C2—C3—C4	−169.2 (13)	C9—C8—C13—C12	2 (2)
C1—C2—C3—C4	72.8 (17)	Cu1—O4—C14—N2	177.0 (11)
N1—C2—C3—C6	70.2 (15)	C16—N2—C14—O4	−176.1 (15)
C1—C2—C3—C6	−47.9 (17)	C15—N2—C14—O4	−5 (2)
C2—C3—C4—C5	52.8 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O2ⁱ	0.96	2.31	3.19 (2)	150

Symmetry code: (i) −x, −y+2, z−1.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₃H₁₃Cl₂NO₃)(C₃H₇NO)]
M_r	438.78
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	298
a, b, c (Å)	11.671 (2), 27.465 (3), 5.8890 (18)
V (Å³)	1887.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.46
Crystal size (mm)	0.43 × 0.15 × 0.13

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.572, 0.833
No. of measured, independent and observed [I > 2σ(I)] reflections	9274, 3260, 2288
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.095, 0.242, 1.05
No. of reflections	3260
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −1.08
Absolute structure	Flack (1983), 1310 Friedel pairs
Absolute structure parameter	0.11 (6)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—O3	1.872 (9)	Cu1—O4	1.920 (9)
Cu1—O1	1.905 (9)	Cu1—N1	1.925 (10)

O3—Cu1—O1	169.2 (4)	O3—Cu1—N1	94.2 (4)
O3—Cu1—O4	92.5 (4)	O1—Cu1—N1	82.7 (4)
O1—Cu1—O4	90.5 (3)	O4—Cu1—N1	173.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O2ⁱ	0.96	2.31	3.19 (2)	150.2

Symmetry code: (i) −x, −y+2, z−1.

Acknowledgements

We acknowledge financial support by the Key Laboratory of Non-ferrous Metal Materials and New Processing Technology, Ministry of Education, China.

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