Dichlorido-2κCl-{μ-6,6'-dimeth-oxy-2,2'-[propane-1,3-diylbis(nitrilo-methyl-idyne)]diphenolato-1κO,N,N',O:2κO,O}copper(II)zinc(II).

In the title compound, [CuZnCl(2)(C(19)H(20)N(2)O(4))], the Cu(II) ion exhibits a slightly distorted square-planar coordination geometry defined by two N atoms and two O atoms of the 6,6'-dimeth-oxy-2,2'-[propane-1,3-diylbis(nitrilo-methyl-idyne)]diphenolate Schiff base ligand. The Zn(II) ion is also four-coordinated by the two phenolate O atoms of the Schiff base ligand and by two cis-coordinated chloride anions.

Related literature

For the physical and chemical properties of heterometallic complexes, see: Ni et al. (2005 ▶, 2007 ▶); Ward (2007 ▶) and for their roles in biological systems, see: Karlin (1993 ▶). For bond-length data, see: Korupoju et al. (2000 ▶); Gheorghe et al. (2006 ▶). For the restraints used in the refinement, see: Ng (2005 ▶).

Experimental

Crystal data

[CuZnCl2(C19H20N2O4)]

M = 540.18

Orthorhombic,

a = 13.0181 (9) Å

b = 10.8503 (8) Å

c = 14.7758 (11) Å

V = 2087.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.45 mm−1

T = 298 K

0.20 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.744, T max = 0.828

9818 measured reflections

3486 independent reflections

3084 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.074

S = 1.07

3486 reflections

262 parameters

13 restraints

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.58 e Å−3

Absolute structure: Flack (1983 ▶), 1564 Friedel pairs

Flack parameter: 0.006 (15)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: XP in SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006928/hg2482sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006928/hg2482Isup2.hkl

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

[CuZnCl2(C19H20N2O4)]	F(000) = 1092
Mr = 540.18	Dx = 1.719 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 4074 reflections
a = 13.0181 (9) Å	θ = 2.5–26.1°
b = 10.8503 (8) Å	µ = 2.45 mm−1
c = 14.7758 (11) Å	T = 298 K
V = 2087.1 (3) Å3	Needle, green
Z = 4	0.20 × 0.10 × 0.08 mm

Bruker APEXII CCD area-detector diffractometer	3486 independent reflections
Radiation source: fine-focus sealed tube	3084 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 0 pixels mm-1	θmax = 25.0°, θmin = 1.9°
φ and ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −11→12
Tmin = 0.744, Tmax = 0.828	l = −17→15
9818 measured reflections

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0389P)2 + 0.0971P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3486 reflections	Δρmax = 0.63 e Å−3
262 parameters	Δρmin = −0.58 e Å−3
13 restraints	Absolute structure: Flack (1983), 1564 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.006 (15)

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
Zn1	0.59914 (3)	0.74035 (3)	0.69902 (3)	0.04337 (13)
Cu1	0.59183 (3)	1.03456 (3)	0.71028 (4)	0.04411 (14)
Cl2	0.71295 (8)	0.63787 (10)	0.78281 (9)	0.0590 (3)
Cl1	0.48653 (8)	0.64556 (11)	0.60882 (10)	0.0653 (4)
O1	0.4768 (2)	0.6796 (3)	0.8322 (2)	0.0607 (8)
O4	0.7243 (2)	0.7042 (2)	0.5679 (2)	0.0531 (7)
O3	0.6649 (2)	0.9031 (2)	0.6508 (2)	0.0468 (7)
C6	0.3763 (3)	0.9888 (5)	0.8239 (3)	0.0537 (12)
N1	0.4874 (3)	1.1465 (3)	0.7582 (3)	0.0596 (10)
O2	0.5262 (2)	0.8915 (2)	0.76318 (19)	0.0442 (7)
C12	0.7778 (4)	1.1331 (3)	0.6360 (3)	0.0486 (10)
H12	0.8230	1.1989	0.6294	0.058*
C15	0.9470 (4)	0.9069 (4)	0.5223 (3)	0.0557 (11)
H15	1.0118	0.9054	0.4958	0.067*
C13	0.8147 (3)	1.0147 (3)	0.6042 (3)	0.0421 (9)
C7	0.4389 (3)	0.8850 (4)	0.8080 (3)	0.0445 (10)
C17	0.7914 (3)	0.8007 (4)	0.5642 (3)	0.0439 (9)
C5	0.2819 (3)	0.9734 (5)	0.8696 (3)	0.0650 (13)
H5	0.2399	1.0415	0.8793	0.078*
C18	0.7549 (3)	0.9076 (3)	0.6083 (3)	0.0388 (8)
C1	0.4576 (4)	0.5620 (4)	0.8709 (5)	0.0845 (18)
H1A	0.5132	0.5074	0.8566	0.127*
H1B	0.3947	0.5293	0.8469	0.127*
H1C	0.4518	0.5700	0.9354	0.127*
C3	0.3144 (3)	0.7587 (5)	0.8888 (3)	0.0633 (13)
H3	0.2943	0.6824	0.9113	0.076*
C16	0.8847 (3)	0.8003 (4)	0.5211 (3)	0.0534 (11)
H16	0.9069	0.7298	0.4910	0.064*
C11	0.6734 (4)	1.2928 (3)	0.6876 (5)	0.0794 (15)
H11A	0.7012	1.3144	0.7465	0.095*
H11B	0.7113	1.3392	0.6425	0.095*
C8	0.4053 (4)	1.1105 (4)	0.7987 (4)	0.0592 (13)
H8	0.3586	1.1722	0.8135	0.071*
C19	0.7605 (4)	0.5875 (4)	0.5382 (4)	0.0653 (13)
H19A	0.7066	0.5276	0.5440	0.098*
H19B	0.8181	0.5630	0.5747	0.098*
H19C	0.7814	0.5930	0.4761	0.098*
C2	0.4077 (3)	0.7705 (4)	0.8442 (3)	0.0506 (11)
N2	0.6914 (3)	1.1585 (3)	0.6717 (3)	0.0499 (9)
C10	0.5740 (5)	1.3279 (5)	0.6847 (5)	0.0981 (17)
H10A	0.5504	1.3104	0.6237	0.118*
H10B	0.5739	1.4168	0.6909	0.118*
C9	0.4950 (4)	1.2824 (4)	0.7450 (6)	0.098 (3)
H9A	0.4292	1.3114	0.7226	0.118*
H9B	0.5056	1.3199	0.8038	0.118*
C4	0.2511 (4)	0.8598 (5)	0.8999 (3)	0.0700 (14)
H4	0.1877	0.8508	0.9280	0.084*
C14	0.9123 (3)	1.0109 (5)	0.5619 (3)	0.0509 (11)
H14	0.9530	1.0813	0.5615	0.061*

	U11	U22	U33	U12	U13	U23
Zn1	0.0359 (2)	0.0315 (2)	0.0628 (3)	0.00014 (17)	0.0017 (2)	−0.0053 (2)
Cu1	0.0362 (2)	0.0294 (2)	0.0667 (3)	0.00258 (17)	−0.0002 (3)	−0.0082 (3)
Cl2	0.0442 (6)	0.0572 (6)	0.0758 (8)	0.0039 (5)	−0.0013 (5)	0.0129 (6)
Cl1	0.0448 (6)	0.0532 (7)	0.0980 (9)	0.0004 (5)	−0.0096 (6)	−0.0273 (6)
O1	0.0527 (18)	0.0442 (17)	0.085 (2)	−0.0085 (14)	0.0185 (16)	−0.0066 (16)
O4	0.0498 (17)	0.0346 (14)	0.075 (2)	0.0015 (13)	0.0136 (15)	−0.0052 (14)
O3	0.0392 (16)	0.0337 (13)	0.0674 (19)	−0.0005 (11)	0.0092 (14)	−0.0024 (12)
C6	0.039 (2)	0.065 (3)	0.057 (3)	0.009 (2)	0.001 (2)	−0.026 (2)
N1	0.042 (2)	0.0386 (19)	0.099 (3)	0.0044 (15)	−0.0035 (19)	−0.0215 (18)
O2	0.0354 (15)	0.0364 (15)	0.0608 (18)	0.0018 (11)	0.0114 (13)	−0.0094 (12)
C12	0.055 (3)	0.035 (2)	0.055 (2)	−0.0055 (18)	−0.009 (2)	0.0120 (18)
C15	0.040 (2)	0.073 (3)	0.054 (3)	0.002 (2)	0.011 (2)	0.007 (2)
C13	0.037 (2)	0.043 (2)	0.046 (2)	0.0038 (17)	−0.0034 (17)	0.0089 (18)
C7	0.032 (2)	0.052 (3)	0.049 (2)	0.0009 (17)	0.0005 (18)	−0.0173 (18)
C17	0.041 (2)	0.045 (2)	0.046 (2)	0.0089 (18)	0.0035 (18)	0.0039 (18)
C5	0.044 (3)	0.086 (4)	0.064 (3)	0.016 (3)	0.008 (2)	−0.031 (3)
C18	0.034 (2)	0.042 (2)	0.040 (2)	0.0014 (17)	−0.0036 (17)	0.0060 (17)
C1	0.080 (4)	0.046 (3)	0.128 (5)	−0.015 (3)	0.030 (4)	−0.007 (3)
C3	0.050 (3)	0.084 (3)	0.056 (3)	−0.014 (2)	0.016 (2)	−0.019 (3)
C16	0.054 (3)	0.058 (3)	0.048 (3)	0.006 (2)	0.010 (2)	0.000 (2)
C11	0.071 (3)	0.0296 (19)	0.138 (4)	0.0002 (19)	−0.006 (3)	−0.009 (3)
C8	0.049 (3)	0.053 (3)	0.075 (3)	0.017 (2)	−0.009 (2)	−0.031 (2)
C19	0.077 (3)	0.044 (2)	0.075 (3)	0.002 (2)	0.015 (3)	−0.004 (2)
C2	0.040 (2)	0.059 (3)	0.052 (3)	−0.0037 (19)	0.0075 (19)	−0.020 (2)
N2	0.0406 (18)	0.0318 (15)	0.077 (2)	−0.0013 (14)	−0.0081 (17)	−0.0010 (16)
C10	0.102 (3)	0.050 (2)	0.142 (4)	0.014 (2)	−0.011 (3)	−0.001 (3)
C9	0.058 (3)	0.035 (2)	0.201 (8)	0.011 (2)	0.000 (4)	−0.031 (3)
C4	0.051 (3)	0.097 (4)	0.062 (3)	−0.005 (3)	0.021 (2)	−0.022 (3)
C14	0.039 (2)	0.060 (3)	0.054 (3)	−0.006 (2)	0.0008 (19)	0.018 (2)

Zn1—O3	2.088 (3)	C7—C2	1.412 (6)
Zn1—O2	2.119 (2)	C17—C16	1.371 (5)
Zn1—Cl2	2.2280 (12)	C17—C18	1.413 (5)
Zn1—Cl1	2.2324 (12)	C5—C4	1.371 (6)
Cu1—O3	1.926 (3)	C5—H5	0.9300
Cu1—O2	1.936 (3)	C1—H1A	0.9600
Cu1—N2	1.953 (3)	C1—H1B	0.9600
Cu1—N1	1.956 (4)	C1—H1C	0.9600
O1—C2	1.347 (5)	C3—C2	1.388 (6)
O1—C1	1.421 (6)	C3—C4	1.381 (6)
O4—C17	1.364 (5)	C3—H3	0.9300
O4—C19	1.421 (5)	C16—H16	0.9300
O3—C18	1.330 (5)	C11—C10	1.349 (7)
C6—C7	1.409 (6)	C11—N2	1.495 (5)
C6—C5	1.412 (7)	C11—H11A	0.9700
C6—C8	1.423 (7)	C11—H11B	0.9700
N1—C8	1.286 (6)	C8—H8	0.9300
N1—C9	1.490 (6)	C19—H19A	0.9600
O2—C7	1.318 (5)	C19—H19B	0.9600
C12—N2	1.272 (5)	C19—H19C	0.9600
C12—C13	1.450 (5)	C10—C9	1.448 (9)
C12—H12	0.9300	C10—H10A	0.9700
C15—C14	1.350 (6)	C10—H10B	0.9700
C15—C16	1.413 (6)	C9—H9A	0.9700
C15—H15	0.9300	C9—H9B	0.9700
C13—C18	1.400 (5)	C4—H4	0.9300
C13—C14	1.417 (6)	C14—H14	0.9300
O3—Zn1—O2	71.43 (10)	H1A—C1—H1B	109.5
O3—Zn1—Cl2	109.81 (8)	O1—C1—H1C	109.5
O2—Zn1—Cl2	115.82 (9)	H1A—C1—H1C	109.5
O3—Zn1—Cl1	117.09 (9)	H1B—C1—H1C	109.5
O2—Zn1—Cl1	109.24 (8)	C2—C3—C4	120.3 (5)
Cl2—Zn1—Cl1	122.58 (4)	C2—C3—H3	119.8
O3—Cu1—O2	78.97 (10)	C4—C3—H3	119.8
O3—Cu1—N2	92.81 (13)	C17—C16—C15	120.0 (4)
O2—Cu1—N2	164.28 (13)	C17—C16—H16	120.0
O3—Cu1—N1	165.52 (14)	C15—C16—H16	120.0
O2—Cu1—N1	92.58 (14)	C10—C11—N2	114.8 (4)
N2—Cu1—N1	98.00 (15)	C10—C11—H11A	108.6
C2—O1—C1	119.1 (4)	N2—C11—H11A	108.6
C17—O4—C19	117.3 (3)	C10—C11—H11B	108.6
C18—O3—Cu1	128.6 (2)	N2—C11—H11B	108.6
C18—O3—Zn1	123.6 (2)	H11A—C11—H11B	107.5
Cu1—O3—Zn1	105.55 (12)	N1—C8—C6	128.6 (4)
C7—C6—C5	119.2 (5)	N1—C8—H8	115.7
C7—C6—C8	123.0 (4)	C6—C8—H8	115.7
C5—C6—C8	117.7 (4)	O4—C19—H19A	109.5
C8—N1—C9	114.7 (4)	O4—C19—H19B	109.5
C8—N1—Cu1	123.9 (3)	H19A—C19—H19B	109.5
C9—N1—Cu1	121.4 (3)	O4—C19—H19C	109.5
C7—O2—Cu1	128.8 (2)	H19A—C19—H19C	109.5
C7—O2—Zn1	124.7 (2)	H19B—C19—H19C	109.5
Cu1—O2—Zn1	104.01 (11)	O1—C2—C3	125.5 (4)
N2—C12—C13	128.2 (4)	O1—C2—C7	113.7 (3)
N2—C12—H12	115.9	C3—C2—C7	120.8 (4)
C13—C12—H12	115.9	C12—N2—C11	114.5 (4)
C14—C15—C16	119.8 (4)	C12—N2—Cu1	123.9 (3)
C14—C15—H15	120.1	C11—N2—Cu1	121.4 (3)
C16—C15—H15	120.1	C11—C10—C9	124.4 (6)
C18—C13—C14	119.6 (4)	C11—C10—H10A	106.2
C18—C13—C12	122.5 (4)	C9—C10—H10A	106.2
C14—C13—C12	117.7 (4)	C11—C10—H10B	106.2
O2—C7—C6	122.6 (4)	C9—C10—H10B	106.2
O2—C7—C2	119.1 (3)	H10A—C10—H10B	106.4
C6—C7—C2	118.3 (4)	C10—C9—N1	117.7 (5)
O4—C17—C16	125.7 (4)	C10—C9—H9A	107.9
O4—C17—C18	113.3 (3)	N1—C9—H9A	107.9
C16—C17—C18	121.0 (4)	C10—C9—H9B	107.9
C4—C5—C6	121.1 (4)	N1—C9—H9B	107.9
C4—C5—H5	119.4	H9A—C9—H9B	107.2
C6—C5—H5	119.4	C5—C4—C3	120.0 (4)
O3—C18—C13	122.7 (3)	C5—C4—H4	120.0
O3—C18—C17	119.0 (3)	C3—C4—H4	120.0
C13—C18—C17	118.3 (4)	C15—C14—C13	121.1 (4)
O1—C1—H1A	109.5	C15—C14—H14	119.5
O1—C1—H1B	109.5	C13—C14—H14	119.5