{2-[(3,5-Dichloro-2-oxidobenzyl-idene)amino-κN,O]-3-methyl-penta-noato-κO}(N,N'-dimethyl-formamide-κO)copper(II).

In the title compound, [Cu(C(13)H(13)Cl(2)NO(3))(C(3)H(7)NO)], 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-oxidobenzyl-idene)amino]-3-methyl-penta-noate and by one O atom from dimethyl-formamide. 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 octa-hedral 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 = 438.78

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.095

wR(F 2) = 0.242

S = 1.05

3260 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −1.08 e Å−3

Absolute structure: Flack (1983 ▶), with 1915 Friedel pairs

Flack parameter: 0.11 (6)

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800932X/gw2039sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C13H13Cl2NO3)(C3H7NO)]	Dx = 1.544 Mg m−3
Mr = 438.78	Mo Kα radiation λ = 0.71073 Å
Orthorhombic, P21212	Cell parameters from 1991 reflections
a = 11.671 (2) Å	θ = 2.3–20.3º
b = 27.465 (3) Å	µ = 1.46 mm−1
c = 5.8890 (18) Å	T = 298 (2) K
V = 1887.7 (7) Å3	Block, blue
Z = 4	0.43 × 0.15 × 0.13 mm
F000 = 900

Bruker SMART CCD area-detector diffractometer	3260 independent reflections
Radiation source: fine-focus sealed tube	2288 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.087
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→13
Tmin = 0.572, Tmax = 0.833	k = −32→32
9274 measured reflections	l = −6→6

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.095	w = 1/[σ2(Fo2) + (0.1179P)2 + 7.0901P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.242	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.54 e Å−3
3260 reflections	Δρmin = −1.08 e Å−3
226 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1310 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.11 (6)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .