[(2S)-2-(3,5-Dichloro-2-oxidobenzyl­ideneamino)-3-(4-hydroxy­phen­yl)propionato-κ3O,N,O′](dimethyl­formamide-κO)copper(II)

Tan, M.-X.; Chen, Z.-F.; Neng, Z.; Liang, H.

doi:10.1107/S1600536808007939

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages m599-m600

doi:10.1107/S1600536808007939

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[(2S)-2-(3,5-Dichloro-2-oxidobenzylideneamino)-3-(4-hydroxyphenyl)propionato-κ³O,N,O′](dimethylformamide-κO)copper(II)

Ming-Xiong Tan,^a,^b ^* Zhen-Feng Chen,^c Zhou Neng ^b and Hong Liang ^a

^aCollege of Chemistry and Chemical Engineering, Central South University, Changsha, HuNan 410083, People's Republic of China, ^bDepartment of Chemistry and Biology, Yu Lin Normal College, Yulin, Guangxi 537000, People's Republic of China, and ^cKey Laboratory of Medicinal Chemical Resources and Molecular Engineering, Ministry of Education, College of Chemistry and Chemical Engineering, Guangxi Normal University, Yucai Road 15, Guilin 541004, People's Republic of China
^*Correspondence e-mail: tanmx00@163.com

(Received 5 January 2008; accepted 24 March 2008; online 29 March 2008)

In the title complex, [Cu(C₁₆H₁₁Cl₂NO₄)(C₃H₇NO)] , the Cu^II atom is coordinated by two O atoms and one N atom from the tridentate ligand L²⁻ {LH₂ = (2S)-[2-(3,5-dichloro-2-hydroxybenzylidene)imino]-3-(4-hydroxyphenyl)propionic acid} and one O atom from a dimethylformamide molecule, resulting in a slightly distorted square-planar geometry. The structure forms a one-dimensional chain through weak coordination bonds [Cu⋯O 3.080 (1), Cu⋯Cl 3.269 (1) Å] and a three-dimensional network through O—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Li et al. (2008 ); Zhang, Li et al. (2007 ); Zhang, Feng et al. (2007a ,b ). For related literature, see: Xia et al. (2007 ); Liu et al. (2007 ); Cohen et al. (1964 ); Desiraju (1989 ); Zordan et al. (2005 ).

Experimental

Crystal data

[Cu(C₁₆H₁₁Cl₂NO₄)(C₃H₇NO)]
M_r = 488.79
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.8646 (16) Å
b = 13.220 (2) Å
c = 26.850 (3) Å
V = 2081.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.34 mm⁻¹
T = 298 (2) K
0.48 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.532, T_max = 0.786
10650 measured reflections
3638 independent reflections
2915 reflections with I > 2σ(I)
R_int = 0.098

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.148
S = 1.04
3638 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.54 e Å⁻³
Absolute structure: Flack (1983 ), with 1505 Friedel pairs
Flack parameter: 0.04 (3)

Table 1
Selected geometric parameters (Å, °)

Cu1—O4	1.875 (5)
Cu1—O1	1.931 (5)
Cu1—N1	1.934 (5)
Cu1—O5	1.954 (4)

O4—Cu1—O1	169.0 (2)
O4—Cu1—N1	94.2 (2)
O1—Cu1—N1	84.5 (2)
O4—Cu1—O5	90.2 (2)
O1—Cu1—O5	91.9 (2)
N1—Cu1—O5	174.3 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.82	1.87	2.661 (7)	163
C17—H17⋯O4	0.93	2.27	2.743 (8)	111
C18—H18B⋯O1ⁱⁱ	0.96	2.54	3.421 (10)	150
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+2]$ .

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/S1600536808007939/rt2016sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007939/rt2016Isup2.hkl

checkCIF report

Comment top

Halogens have a ubiquitous presence in both inorganic and organic chemistry, serving as mondentate or bridging ligands for a wide variety of d-block, f-block, and main group metals as well being common substituents in a large number of organic compounds. Most frequently they lie at the periphery of molecules. The resultant steric accessibility has the potential for halogenated compounds to be attractive targets for use in supramolecular chemistry and crystal engineering wherein the halogen atoms are directly involved in intermolecular interactions. Indeed, interest in packing arrangements of halogenated compounds goes back many years to what Schmidt called the chloro effect, wherein the presence of chloro substituents on aromatic compounds frequently resulted in stacking arrangements with a resultant short (ca 4 Å) crystallographic axis. (Cohen et al., 1964; Zordan et al., 2005; Cohen et al., 1964; Desiraju, 1989; Zhang, Li et al., 2007). Herein, we chose LH₂ as ligand system, and obtained a new mononuclear copper complex [Cu(L)(C₃H₇NO)] (1).

The title compound, (I), is a chiral Cu^II complex containing a dimethylformamide and a chiral ligand constructed from 3,5-Dichloro-2-hydroxy-benzaldehyde and 2-Amino-3-(4-hydroxy-phenyl)-propionic acid. The asymmetric unit of (I) shows a complex consisting of one Cu^II atom, one L^2- ligand and one dimethylformamide (Fig. 1). The Cu atom is coordinated by two oxygen atoms and one N atom from one tridentate L^2- ligand, to yield a slightly distorted planar geometry with bond lengths Cu1—O1, Cu1—O4, Cu1—O5 and Cu1—N1 1.931 (5), 1.875 (5), 1.954 (4) and 1.934 (5) Å, respectively; and bond angles (cis-angles are in the range of 84.5 (2)–91.9 (2) °, but all trans-angles are 169.0 (2)–174.3 (2) °) (Table 2).

As expected, all other bond distances and angles are within normal range. The structure forms a one-dimensional chain (Fig. 2) through weak coordination bonds (Cu1—O2ⁱ, 3.080 (1) Å, Cu1—Cl1ⁱⁱ, 3.269 (1) Å, symmetry codes: i: 1 + x, y, z; ii: -1 + x, y, z) and a three-dimensional network via weak hydrogen bonds: (O3—H3···O2ⁱ, 2.661 (7) Å, symmetry codes: i: 1 - x, 1/2 + y, 3/2 - z) and C—H···O hydrogen bond (C17—H17···O4, 2.743 (8) Å, C18—H18B···O1ⁱⁱ, 2.536 (4) Å, symmetry code: ii: 1/2 + x,-1/2 - y,2 - z) (Fig. 3).

Related literature top

For related structures, see: Li et al. (2008); Zhang, Li et al. (2007); Zhang, Feng et al. (2007a,b). For related literature, see: Xia et al. (2007); Liu et al. (2007); Cohen et al. (1964); Desiraju (1989); Zordan et al., 2005.

Experimental top

3,5-Dichloro-2-hydroxy-benzaldehyde(0.382 g, 2.0 mmol) and 2-Amino-3-(4-hydroxy-phenyl)-propionic acid (0.3624 g, 2.0 mmol) were dissolved in 10 ml absolute methanol. The mixture was stirred for 1 h at room temperature to yield a yellow solution. To this was added a solution of CuSO₄.5H₂O (0.5 g, 2 mmol) in a mixture of 2 ml DMF and 10 ml me thanol. The mixture was refluxed for 1 h, and then the blue solution was filtered. Blue single crystals suitable for X-ray analysis were obtained by slow evaporation of the above filtrate at room temperature. Yield: 89.6% (based on Copper). Elemental analysis for [Cu(C₁₆H₁₁Cl₂NO₄)(C₃H₇NO)] calculated: C 46.69, H 3.71, N 5.73%; found: C 46.61, H 3.84, N 5.67%.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (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 molecular structure of (I), showing 30% probability displacement ellipsoids for non-H atoms. hydrogen atoms have been omitted.
	Fig. 2. one-dimensional chain of (I).
	Fig. 3. The three-dimensional network of (I) through hydrogen bonds.

(2S)-[2-(3,5-Dichloro-2-oxidobenzylideneamino)-3-(4-hydroxyphenyl)propionato- κ³O,N,O'](dimethylformamide-κO)copper(II) top

Crystal data top

[Cu(C₁₆H₁₁Cl₂NO₄)(C₃H₇NO)]	F(000) = 996
M_r = 488.79	D_x = 1.560 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4089 reflections
a = 5.8646 (16) Å	θ = 2.3–23.8°
b = 13.220 (2) Å	µ = 1.34 mm⁻¹
c = 26.850 (3) Å	T = 298 K
V = 2081.7 (7) Å³	Prism, blue
Z = 4	0.48 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3638 independent reflections
Radiation source: fine-focus sealed tube	2915 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.098
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.532, T_max = 0.786	k = −15→12
10650 measured reflections	l = −31→31

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)] = 0.061	H-atom parameters constrained
wR(F²) = 0.148	w = 1/[σ²(F_o²) + (0.0751P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3638 reflections	Δρ_max = 0.50 e Å⁻³
262 parameters	Δρ_min = −0.54 e Å⁻³
0 restraints	Absolute structure: Flack (1983), with 1505 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (3)

Crystal data top

[Cu(C₁₆H₁₁Cl₂NO₄)(C₃H₇NO)]	V = 2081.7 (7) Å³
M_r = 488.79	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.8646 (16) Å	µ = 1.34 mm⁻¹
b = 13.220 (2) Å	T = 298 K
c = 26.850 (3) Å	0.48 × 0.20 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3638 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2915 reflections with I > 2σ(I)
T_min = 0.532, T_max = 0.786	R_int = 0.098
10650 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	H-atom parameters constrained
wR(F²) = 0.148	Δρ_max = 0.50 e Å⁻³
S = 1.04	Δρ_min = −0.54 e Å⁻³
3638 reflections	Absolute structure: Flack (1983), with 1505 Friedel pairs
262 parameters	Absolute structure parameter: 0.04 (3)
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	0.87095 (14)	0.01109 (5)	0.92554 (2)	0.0398 (2)
Cl1	1.5356 (3)	0.15751 (14)	0.99080 (6)	0.0542 (5)
Cl2	1.5314 (5)	0.4447 (2)	0.84884 (10)	0.1123 (10)
N1	0.7954 (8)	0.0937 (4)	0.86843 (16)	0.0341 (12)
N2	1.2035 (10)	−0.1364 (5)	1.03525 (19)	0.0502 (15)
O1	0.5867 (8)	−0.0565 (3)	0.91109 (13)	0.0447 (11)
O2	0.2837 (8)	−0.0471 (4)	0.86065 (16)	0.0507 (12)
O3	0.9847 (9)	0.2916 (4)	0.64815 (17)	0.0663 (15)
H3	0.8857	0.3335	0.6420	0.099*
O4	1.1115 (8)	0.0946 (3)	0.94609 (13)	0.0426 (10)
O5	0.9417 (9)	−0.0841 (4)	0.97899 (16)	0.0566 (14)
C1	0.4783 (12)	−0.0227 (4)	0.8738 (2)	0.0371 (14)
C2	0.5969 (10)	0.0579 (4)	0.84153 (18)	0.0335 (13)
H2	0.4921	0.1145	0.8357	0.040*
C3	0.6629 (11)	0.0092 (4)	0.79128 (18)	0.0413 (15)
H3A	0.7794	−0.0416	0.7971	0.050*
H3B	0.5305	−0.0249	0.7776	0.050*
C4	0.7505 (11)	0.0844 (5)	0.7537 (2)	0.0390 (15)
C5	0.6177 (12)	0.1646 (5)	0.7384 (2)	0.0470 (16)
H5	0.4740	0.1726	0.7525	0.056*
C6	0.6887 (12)	0.2333 (5)	0.7032 (2)	0.0478 (18)
H6	0.5919	0.2850	0.6930	0.057*
C7	0.9055 (11)	0.2249 (5)	0.6832 (2)	0.0436 (16)
C8	1.0373 (13)	0.1453 (5)	0.6970 (2)	0.0552 (18)
H8	1.1793	0.1369	0.6822	0.066*
C9	0.9657 (12)	0.0762 (5)	0.7326 (2)	0.0477 (17)
H9	1.0625	0.0241	0.7424	0.057*
C10	0.8988 (10)	0.1759 (4)	0.85633 (19)	0.0335 (13)
H10	0.8373	0.2130	0.8301	0.040*
C11	1.1005 (11)	0.2157 (4)	0.87951 (19)	0.0367 (14)
C12	1.1995 (9)	0.1712 (4)	0.9226 (2)	0.0346 (13)
C13	1.4061 (11)	0.2142 (5)	0.93978 (19)	0.0372 (14)
C14	1.5016 (12)	0.2978 (5)	0.9188 (2)	0.0527 (18)
H14	1.6334	0.3259	0.9322	0.063*
C15	1.4005 (14)	0.3402 (5)	0.8774 (3)	0.062 (2)
C16	1.2032 (12)	0.3018 (5)	0.8584 (3)	0.0508 (18)
H16	1.1354	0.3329	0.8311	0.061*
C17	1.1375 (15)	−0.0875 (5)	0.9947 (3)	0.0558 (18)
H17	1.2486	−0.0531	0.9767	0.067*
C18	1.0416 (14)	−0.1899 (7)	1.0655 (3)	0.073 (2)
H18A	1.0066	−0.1505	1.0945	0.110*
H18B	1.1053	−0.2537	1.0754	0.110*
H18C	0.9048	−0.2013	1.0467	0.110*
C19	1.4387 (14)	−0.1337 (7)	1.0521 (3)	0.078 (3)
H19A	1.5335	−0.1067	1.0261	0.118*
H19B	1.4881	−0.2010	1.0601	0.118*
H19C	1.4502	−0.0917	1.0811	0.118*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0472 (4)	0.0363 (4)	0.0360 (3)	−0.0017 (4)	−0.0031 (3)	0.0056 (3)
Cl1	0.0510 (10)	0.0635 (11)	0.0481 (8)	0.0039 (9)	−0.0144 (7)	−0.0136 (8)
Cl2	0.117 (2)	0.0863 (18)	0.133 (2)	−0.0606 (17)	−0.0291 (18)	0.0441 (15)
N1	0.037 (3)	0.031 (3)	0.034 (2)	0.009 (2)	0.001 (2)	−0.002 (2)
N2	0.045 (3)	0.056 (4)	0.050 (3)	0.007 (3)	−0.001 (3)	0.022 (3)
O1	0.056 (3)	0.039 (2)	0.039 (2)	−0.010 (2)	0.001 (2)	0.0045 (17)
O2	0.043 (3)	0.048 (3)	0.060 (3)	−0.008 (2)	0.004 (2)	−0.009 (2)
O3	0.070 (4)	0.058 (3)	0.071 (3)	0.012 (3)	0.034 (3)	0.015 (3)
O4	0.047 (3)	0.045 (2)	0.0357 (19)	0.005 (2)	−0.003 (2)	−0.0015 (18)
O5	0.060 (4)	0.055 (3)	0.055 (3)	0.002 (3)	−0.006 (2)	0.024 (2)
C1	0.043 (4)	0.027 (3)	0.041 (3)	0.003 (3)	0.001 (3)	−0.007 (3)
C2	0.024 (3)	0.040 (3)	0.037 (3)	0.000 (3)	−0.005 (3)	−0.004 (2)
C3	0.049 (4)	0.039 (3)	0.036 (3)	−0.003 (4)	−0.003 (3)	−0.005 (3)
C4	0.043 (4)	0.040 (4)	0.034 (3)	0.005 (3)	−0.007 (3)	−0.003 (3)
C5	0.036 (3)	0.067 (4)	0.038 (3)	0.007 (4)	0.003 (3)	0.005 (3)
C6	0.046 (4)	0.050 (4)	0.047 (4)	0.015 (3)	0.003 (3)	0.007 (3)
C7	0.043 (4)	0.051 (4)	0.037 (3)	0.004 (4)	0.005 (3)	0.001 (3)
C8	0.048 (4)	0.062 (5)	0.056 (4)	0.010 (4)	0.014 (3)	0.007 (3)
C9	0.041 (4)	0.046 (4)	0.056 (4)	0.009 (3)	0.007 (3)	−0.006 (3)
C10	0.032 (3)	0.034 (3)	0.034 (3)	−0.001 (3)	0.000 (3)	0.001 (2)
C11	0.038 (4)	0.035 (3)	0.037 (3)	0.001 (3)	0.004 (3)	−0.001 (2)
C12	0.027 (3)	0.036 (3)	0.041 (3)	0.005 (3)	0.006 (3)	−0.017 (3)
C13	0.035 (4)	0.045 (4)	0.032 (3)	0.003 (3)	0.001 (3)	−0.013 (2)
C14	0.045 (4)	0.052 (4)	0.061 (4)	−0.010 (4)	−0.005 (4)	−0.015 (3)
C15	0.060 (5)	0.052 (4)	0.073 (5)	−0.013 (4)	−0.001 (4)	0.009 (4)
C16	0.050 (4)	0.038 (4)	0.064 (4)	−0.012 (3)	−0.002 (4)	0.014 (3)
C17	0.055 (5)	0.048 (4)	0.065 (4)	0.009 (4)	0.001 (4)	0.021 (3)
C18	0.063 (5)	0.093 (6)	0.064 (5)	0.001 (5)	0.003 (4)	0.038 (4)
C19	0.055 (5)	0.092 (7)	0.088 (5)	0.003 (5)	−0.017 (4)	0.037 (5)

Geometric parameters (Å, º) top

Cu1—O4	1.875 (5)	C5—C6	1.374 (9)
Cu1—O1	1.931 (5)	C5—H5	0.9300
Cu1—N1	1.934 (5)	C6—C7	1.385 (9)
Cu1—O5	1.954 (4)	C6—H6	0.9300
Cl1—C13	1.736 (6)	C7—C8	1.357 (9)
Cl2—C15	1.756 (7)	C8—C9	1.387 (9)
N1—C10	1.286 (7)	C8—H8	0.9300
N1—C2	1.449 (7)	C9—H9	0.9300
N2—C17	1.324 (8)	C10—C11	1.437 (8)
N2—C18	1.435 (9)	C10—H10	0.9300
N2—C19	1.452 (9)	C11—C16	1.407 (8)
O1—C1	1.267 (7)	C11—C12	1.423 (8)
O2—C1	1.238 (7)	C12—C13	1.416 (8)
O3—C7	1.371 (7)	C13—C14	1.361 (9)
O3—H3	0.8200	C14—C15	1.379 (10)
O4—C12	1.299 (7)	C14—H14	0.9300
O5—C17	1.224 (9)	C15—C16	1.362 (10)
C1—C2	1.540 (8)	C16—H16	0.9300
C2—C3	1.545 (7)	C17—H17	0.9300
C2—H2	0.9800	C18—H18A	0.9600
C3—C4	1.508 (8)	C18—H18B	0.9600
C3—H3A	0.9700	C18—H18C	0.9600
C3—H3B	0.9700	C19—H19A	0.9600
C4—C5	1.378 (9)	C19—H19B	0.9600
C4—C9	1.387 (9)	C19—H19C	0.9600

O4—Cu1—O1	169.0 (2)	C7—C8—C9	121.8 (7)
O4—Cu1—N1	94.2 (2)	C7—C8—H8	119.1
O1—Cu1—N1	84.5 (2)	C9—C8—H8	119.1
O4—Cu1—O5	90.2 (2)	C4—C9—C8	120.3 (7)
O1—Cu1—O5	91.9 (2)	C4—C9—H9	119.9
N1—Cu1—O5	174.3 (2)	C8—C9—H9	119.9
C10—N1—C2	121.9 (5)	N1—C10—C11	126.1 (5)
C10—N1—Cu1	124.7 (4)	N1—C10—H10	117.0
C2—N1—Cu1	113.3 (4)	C11—C10—H10	117.0
C17—N2—C18	120.8 (6)	C16—C11—C12	119.2 (6)
C17—N2—C19	121.4 (7)	C16—C11—C10	118.3 (5)
C18—N2—C19	117.7 (6)	C12—C11—C10	122.5 (5)
C1—O1—Cu1	115.4 (4)	O4—C12—C13	119.7 (5)
C7—O3—H3	109.5	O4—C12—C11	123.7 (5)
C12—O4—Cu1	128.0 (4)	C13—C12—C11	116.6 (6)
C17—O5—Cu1	118.4 (5)	C14—C13—C12	122.9 (6)
O2—C1—O1	126.6 (6)	C14—C13—Cl1	119.8 (5)
O2—C1—C2	115.8 (5)	C12—C13—Cl1	117.2 (5)
O1—C1—C2	117.6 (5)	C13—C14—C15	119.2 (7)
N1—C2—C1	107.9 (4)	C13—C14—H14	120.4
N1—C2—C3	111.7 (5)	C15—C14—H14	120.4
C1—C2—C3	108.4 (5)	C16—C15—C14	121.0 (7)
N1—C2—H2	109.6	C16—C15—Cl2	120.1 (6)
C1—C2—H2	109.6	C14—C15—Cl2	118.9 (6)
C3—C2—H2	109.6	C15—C16—C11	121.0 (7)
C4—C3—C2	113.3 (5)	C15—C16—H16	119.5
C4—C3—H3A	108.9	C11—C16—H16	119.5
C2—C3—H3A	108.9	O5—C17—N2	125.2 (7)
C4—C3—H3B	108.9	O5—C17—H17	117.4
C2—C3—H3B	108.9	N2—C17—H17	117.4
H3A—C3—H3B	107.7	N2—C18—H18A	109.5
C5—C4—C9	117.0 (6)	N2—C18—H18B	109.5
C5—C4—C3	121.0 (6)	H18A—C18—H18B	109.5
C9—C4—C3	122.1 (6)	N2—C18—H18C	109.5
C6—C5—C4	122.8 (7)	H18A—C18—H18C	109.5
C6—C5—H5	118.6	H18B—C18—H18C	109.5
C4—C5—H5	118.6	N2—C19—H19A	109.5
C5—C6—C7	119.4 (6)	N2—C19—H19B	109.5
C5—C6—H6	120.3	H19A—C19—H19B	109.5
C7—C6—H6	120.3	N2—C19—H19C	109.5
C8—C7—O3	119.5 (6)	H19A—C19—H19C	109.5
C8—C7—C6	118.6 (6)	H19B—C19—H19C	109.5
O3—C7—C6	121.7 (6)

O4—Cu1—N1—C10	−0.5 (5)	O3—C7—C8—C9	179.5 (6)
O1—Cu1—N1—C10	168.5 (5)	C6—C7—C8—C9	−3.9 (11)
O4—Cu1—N1—C2	−176.4 (4)	C5—C4—C9—C8	−1.5 (10)
O1—Cu1—N1—C2	−7.4 (3)	C3—C4—C9—C8	178.0 (6)
O4—Cu1—O1—C1	83.8 (9)	C7—C8—C9—C4	2.9 (11)
N1—Cu1—O1—C1	0.1 (4)	C2—N1—C10—C11	−177.8 (5)
O5—Cu1—O1—C1	−175.4 (4)	Cu1—N1—C10—C11	6.6 (8)
O1—Cu1—O4—C12	−90.9 (9)	N1—C10—C11—C16	174.1 (6)
N1—Cu1—O4—C12	−8.1 (5)	N1—C10—C11—C12	−5.7 (9)
O5—Cu1—O4—C12	168.2 (5)	Cu1—O4—C12—C13	−168.8 (4)
O4—Cu1—O5—C17	−26.4 (6)	Cu1—O4—C12—C11	10.8 (8)
O1—Cu1—O5—C17	164.4 (6)	C16—C11—C12—O4	176.7 (5)
Cu1—O1—C1—O2	−172.3 (5)	C10—C11—C12—O4	−3.5 (8)
Cu1—O1—C1—C2	7.0 (6)	C16—C11—C12—C13	−3.7 (8)
C10—N1—C2—C1	−164.2 (5)	C10—C11—C12—C13	176.1 (5)
Cu1—N1—C2—C1	11.9 (5)	O4—C12—C13—C14	−176.3 (5)
C10—N1—C2—C3	76.7 (7)	C11—C12—C13—C14	4.1 (8)
Cu1—N1—C2—C3	−107.2 (4)	O4—C12—C13—Cl1	2.3 (7)
O2—C1—C2—N1	166.9 (5)	C11—C12—C13—Cl1	−177.3 (4)
O1—C1—C2—N1	−12.5 (7)	C12—C13—C14—C15	−3.4 (10)
O2—C1—C2—C3	−71.9 (6)	Cl1—C13—C14—C15	178.1 (5)
O1—C1—C2—C3	108.7 (5)	C13—C14—C15—C16	2.2 (11)
N1—C2—C3—C4	−69.3 (6)	C13—C14—C15—Cl2	−177.3 (5)
C1—C2—C3—C4	171.9 (5)	C14—C15—C16—C11	−2.0 (11)
C2—C3—C4—C5	−59.0 (7)	Cl2—C15—C16—C11	177.5 (6)
C2—C3—C4—C9	121.5 (6)	C12—C11—C16—C15	2.8 (10)
C9—C4—C5—C6	1.3 (10)	C10—C11—C16—C15	−177.0 (6)
C3—C4—C5—C6	−178.2 (6)	Cu1—O5—C17—N2	169.3 (5)
C4—C5—C6—C7	−2.4 (10)	C18—N2—C17—O5	−1.1 (12)
C5—C6—C7—C8	3.6 (10)	C19—N2—C17—O5	−178.0 (8)
C5—C6—C7—O3	−179.8 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	1.87	2.661 (7)	163
C17—H17···O4	0.93	2.27	2.743 (8)	111
C18—H18B···O1ⁱⁱ	0.96	2.54	3.421 (10)	150

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1/2, −y−1/2, −z+2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₆H₁₁Cl₂NO₄)(C₃H₇NO)]
M_r	488.79
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	5.8646 (16), 13.220 (2), 26.850 (3)
V (Å³)	2081.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.34
Crystal size (mm)	0.48 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.532, 0.786
No. of measured, independent and observed [I > 2σ(I)] reflections	10650, 3638, 2915
R_int	0.098
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.148, 1.04
No. of reflections	3638
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.54
Absolute structure	Flack (1983), with 1505 Friedel pairs
Absolute structure parameter	0.04 (3)

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

Selected geometric parameters (Å, º) top

Cu1—O4	1.875 (5)	Cu1—N1	1.934 (5)
Cu1—O1	1.931 (5)	Cu1—O5	1.954 (4)

O4—Cu1—O1	169.0 (2)	O4—Cu1—O5	90.2 (2)
O4—Cu1—N1	94.2 (2)	O1—Cu1—O5	91.9 (2)
O1—Cu1—N1	84.5 (2)	N1—Cu1—O5	174.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	1.87	2.661 (7)	163
C17—H17···O4	0.93	2.27	2.743 (8)	111
C18—H18B···O1ⁱⁱ	0.96	2.54	3.421 (10)	150

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1/2, −y−1/2, −z+2.

Acknowledgements

We acknowledge financial support by the NSFC (grant No. 20561001) and the EDF of Guangxi (grant No. 200607LX067).

References

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