[(2S)-2-(3,5-Dichloro-2-oxidobenzyl-ideneamino)-3-(4-hydroxy-phen-yl)propionato-κO,N,O'](dimethyl-formamide-κO)copper(II).

In the title complex, [Cu(C(16)H(11)Cl(2)NO(4))(C(3)H(7)NO)] , the Cu(II) atom is coordinated by two O atoms and one N atom from the tridentate ligand L(2-) {LH(2) = (2S)-[2-(3,5-dichloro-2-hydroxy-benzyl-idene)-imino]-3-(4-hydroxy-phenyl)propionic acid} and one O atom from a dimethyl-formamide mol-ecule, 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 = 488.79

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.148

S = 1.04

3638 reflections

262 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.54 e Å−3

Absolute structure: Flack (1983 ▶), with 1505 Friedel pairs

Flack parameter: 0.04 (3)

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/S1600536808007939/rt2016sup1.cif

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

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

[Cu(C16H11Cl2NO4)(C3H7NO)]	F000 = 996
Mr = 488.79	Dx = 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 = 2.3–23.8º
b = 13.220 (2) Å	µ = 1.34 mm−1
c = 26.850 (3) Å	T = 298 (2) K
V = 2081.7 (7) Å3	Prism, blue
Z = 4	0.48 × 0.20 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	3638 independent reflections
Radiation source: fine-focus sealed tube	2915 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.098
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.532, Tmax = 0.786	k = −15→12
10650 measured reflections	l = −31→31

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.061	w = 1/[σ2(Fo2) + (0.0751P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.148	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.50 e Å−3
3638 reflections	Δρmin = −0.54 e Å−3
262 parameters	Extinction correction: none
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 1505 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.04 (3)

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	0.87095 (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*

	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)

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)

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

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) ; (ii) .