{[μ-N,N′-Bis­(salicyl­idene)-1,3-propane­diaminato-N,N′-di­methyl­form­amide]­zinc(II)}di­chlorozinc(II)

Tatar, L.; Atakol, O.; Ülkü, D.

doi:10.1107/S1600536802001678

{[μ-N,N′-Bis(salicylidene)-1,3-propanediaminato-N,N′-dimethylformamide]zinc(II)}dichlorozinc(II)

The title compound, [Zn₂Cl₂(C₁₇H₁₆N₂O₂)(C₃H₇NO)], is a doubly oxygen-bridged dinuclear complex with non-crystallographic mirror symmetry. One of the Zn²⁺ ions has a distorted square-pyramidal environment involving two O and two N atoms of the bis(salicylidene)-1,3-propanediaminate ligand, and an O atom of dimethylformamide in the axial position. The other Zn²⁺ ion has a distorted tetrahedral coordination, with average Zn—O and Zn—Cl distances of 1.994 (3) and 2.2108 (14) Å. The Zn

Zn distance is 3.161 (1) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001678/ob6112sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001678/ob6112Isup2.hkl Contains datablock I

CCDC reference: 182573

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.029
wR factor = 0.090
Data-to-parameter ratio = 10.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.17
         From the CIF: _reflns_number_total               2927
         Count of symmetry unique reflns         2928
         Completeness (_total/calc)             99.97%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure

Comment top

Dinuclear complexes with double oxygen bridges are of interest because of the magnetic superexchange interactions between the bridged metal ions. The magnetic properties of homo- and heteropolynuclear compounds are curently under investigation (Tuna et al., 1999). The synthesis and structures of oxygen-bridged polynuclear complexes based on Schiff base ligands, such as [Zn{Zn(CH₃COO)(SALPD)}₂] (Ülkü et al., 2001, and references therein), [ZnBr₂Ni(SALPD)(C₃H₇NO)₂] (Arıcı et al., 2001), [ZnCl₂Cu(SALPD)] (Tatar et al., 1999), [ZnCl₂Zn(SALPD)(C₂H₇O₂)] (Atakol et al., 1999a), [ZnCl₂Ni(SALPD)(C₆H₇N)₂] (Atakol et al., 1999b), [ZnI₂Cu(SALPD)] (Ercan et al., 1999a) and [ZnI₂Cu(SALPD)(C₆H₇N)] (Ercan et al., 1999b) [SALPD is N,N'-bis(salicylidene)-1,3-propanediaminate (C₁₇H₁₆N₂O₂)], have been the subject of considerable interest in our laboratory.

In the present work, a zinc–Schiff base complex, [ZnCl₂Zn(SALPD)(C₃H₇NO)], (I), consisting of a doubly oxygen-bridged homodinuclear structure was prepared, and the crystal structure of this new dimeric complex determined. The coordination around the Zn1 ion is a distorted square pyramid. The basal plane, defined by the O1, O2, N1 and N2 atoms, consists of two N atoms and two bridging O atoms from a bis(salicylidene)-1,3-propanediaminate (SALPD^2-) ligand. The axial position of the square pyramid is occupied by an O atom [Zn1—O3 2.041 (3) Å] of the dimethylformamide group. Within the coordination sphere, the average Zn1—N and Zn1—O (SALPD^2-) bond lengths are 2.043 (3) and 2.053 (3) Å, respectively. The bond angles in the five-coordinated polyhedra have values between 75.90 (10) (O1—Zn1—O2) and 105.60 (14)° (O3—Zn1—N1). The dihedral angle between the O1—Zn1—O2 and N1—Zn1—N2 planes is 32.78 (1)°. The Zn1 ion is located 0.412 (3) Å from the basal plane towards the O3 atom.

The Zn2 ion has a distorted tetrahedral coordination involving two bridging O atoms from the SALPD^2- ligand and two Cl atoms. The Zn2—O1, Zn2—O2, Zn2—Cl1 and Zn2—Cl2 bond lengths are 1.991 (3), 1.997 (3), 2.2163 (14) and 2.2054 (14) Å, respectively. The Cl1—Zn2—Cl2 and O1—Zn2—O2 angles are 119.75 (7) and 78.56 (10)°, respectively, and these two planes almost perpendicular to each other, the dihedral angle being 89.82 (1)°.

The bridging plane (Zn1—O1—Zn2—O2) in the title compound is not exactly planar, as also observed in the corresponding Cu—Zn complex, [(II), Tatar et al., 1999]. The planes through atoms O1—Zn1—O2 and O1—Zn2—O2 have a dihedral angle of 3.07 (1)° between them; this is smaller than the value of 14.04 (4)° observed in (II). The bridging plane and the coordinaton plane composed of atoms O1, N1, O2 and N2 around the Zn1 ion form a dihedral angle of 16.03 (1)°, which is greater than the values for related compounds: 0.44 (9)° (Atakol et al., 1999b), 1.9 (3)° (Ercan et al., 1999a), 8.6 (5)° (Tatar et al., 1999), and 11.4 (4)° (Ercan et al., 1999b). In the molecule, the Zn1···Zn2 separation is 3.161 (1) Å.

In compound (I), the SALPD^2- ligand is not planar; the six-membered chelate ring composed of atoms Zn1, N1, C8, C9, C10 and N2 has a chair conformation and the diagonally positioned atoms (Zn1 and C9) are displaced from the plane defined by the other four atoms of the ring by 0.278 (3) and -0.717 (3) Å, respectively. The phenyl rings are almost planar and the average bond lengths and bond angles in the phenyl rings are 1.390 Å and 119.99°.

Experimental top

The ligand N,N'-bis(salicylidene)-1,3-propanediamine (0.282 g, 1 mmol) was dissolved in a dimethylformamide (dmf)–acetonitrile (MeCN) mixture (30 ml 1:2) by heating. A solution of ZnCl₂ (0.272 g, 2 mmol) in hot dmf (20 ml) was added. The resulting mixture was set aside for 10 d and the crystals which formed were filtered off and dried in air.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. ORTEP-3 (Farrugia, 1997) drawings of [Zn₂Cl₂(C₁₇H₁₆N₂O₂)(C₃H₇NO)] with the atom-numbering schemes. The displacement ellipsoids are drawn at the 40% probability level.

(I) top

Crystal data top

[Zn₂Cl₂(C₁₇H₁₆N₂O₂)(C₃H₇NO)]	F(000) = 1128
M_r = 555.09	D_x = 1.581 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2bc	Cell parameters from 25 reflections
a = 10.1959 (9) Å	θ = 10.4–18.3°
b = 14.443 (3) Å	µ = 2.31 mm⁻¹
c = 15.8359 (15) Å	T = 293 K
V = 2332.0 (5) Å³	Prism, colorless
Z = 4	0.40 × 0.40 × 0.40 mm

Data collection top

Enraf Nonius CAD4 diffractometer	2718 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.015
Graphite monochromator	θ_max = 27.2°, θ_min = 2.5°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→18
T_min = 0.383, T_max = 0.397	l = −20→0
2929 measured reflections	3 standard reflections every 120 min
2927 independent reflections	intensity decay: 2%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.029	w = 1/[σ²(F_o²) + (0.0568P)² + 0.9618P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.090	(Δ/σ)_max < 0.001
S = 1.11	Δρ_max = 0.68 e Å⁻³
2927 reflections	Δρ_min = −0.41 e Å⁻³
272 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0136 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: (Flack, 1983), no Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.01 (2)

Crystal data top

[Zn₂Cl₂(C₁₇H₁₆N₂O₂)(C₃H₇NO)]	V = 2332.0 (5) Å³
M_r = 555.09	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.1959 (9) Å	µ = 2.31 mm⁻¹
b = 14.443 (3) Å	T = 293 K
c = 15.8359 (15) Å	0.40 × 0.40 × 0.40 mm

Data collection top

Enraf Nonius CAD4 diffractometer	2718 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.015
T_min = 0.383, T_max = 0.397	3 standard reflections every 120 min
2929 measured reflections	intensity decay: 2%
2927 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.090	Δρ_max = 0.68 e Å⁻³
S = 1.11	Δρ_min = −0.41 e Å⁻³
2927 reflections	Absolute structure: (Flack, 1983), no Friedel pairs
272 parameters	Absolute structure parameter: −0.01 (2)
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. Number of psi-scan sets used was 7 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

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
C1	0.4857 (4)	0.0231 (3)	0.2883 (2)	0.0309 (8)
C2	0.5789 (5)	−0.0323 (4)	0.3289 (3)	0.0451 (11)
H2	0.6403	−0.0641	0.2966	0.054*
C3	0.5822 (6)	−0.0409 (4)	0.4157 (3)	0.0487 (12)
H3	0.6458	−0.0778	0.4410	0.058*
C4	0.4918 (6)	0.0049 (4)	0.4651 (3)	0.0492 (12)
H4	0.4946	−0.0002	0.5236	0.059*
C5	0.3972 (5)	0.0583 (3)	0.4264 (3)	0.0454 (12)
H5	0.3349	0.0884	0.4593	0.054*
C6	0.3930 (4)	0.0680 (3)	0.3379 (2)	0.0341 (9)
C7	0.2915 (4)	0.1283 (3)	0.3063 (3)	0.0401 (9)
H7	0.2433	0.1605	0.3466	0.048*
C8	0.1476 (5)	0.2068 (4)	0.2139 (3)	0.0516 (12)
H8A	0.0678	0.1709	0.2082	0.062*
H8B	0.1377	0.2469	0.2627	0.062*
C9	0.1650 (5)	0.2644 (3)	0.1378 (3)	0.0569 (12)
H9A	0.2529	0.2901	0.1387	0.068*
H9B	0.1040	0.3159	0.1408	0.068*
C10	0.1452 (5)	0.2157 (4)	0.0543 (3)	0.0531 (12)
H10A	0.0642	0.1805	0.0563	0.064*
H10B	0.1368	0.2616	0.0099	0.064*
C11	0.2803 (4)	0.1439 (3)	−0.0446 (3)	0.0379 (9)
H11	0.2287	0.1781	−0.0815	0.046*
C12	0.3802 (4)	0.0870 (3)	−0.0828 (2)	0.0322 (8)
C13	0.3796 (5)	0.0798 (4)	−0.1714 (3)	0.0430 (10)
H13	0.3150	0.1109	−0.2016	0.052*
C14	0.4702 (5)	0.0289 (3)	−0.2148 (3)	0.0435 (11)
H14	0.4663	0.0248	−0.2734	0.052*
C15	0.5677 (6)	−0.0163 (4)	−0.1703 (3)	0.0469 (11)
H15	0.6299	−0.0510	−0.1993	0.056*
C16	0.5738 (5)	−0.0104 (3)	−0.0835 (3)	0.0391 (10)
H16	0.6399	−0.0415	−0.0546	0.047*
C17	0.4810 (4)	0.0420 (3)	−0.0379 (3)	0.0320 (9)
C18	0.3079 (4)	−0.1207 (3)	0.1199 (3)	0.0431 (9)
H18	0.3989	−0.1160	0.1212	0.052*
C19	0.1181 (6)	−0.2199 (4)	0.1140 (5)	0.0712 (17)
H19A	0.1011	−0.2853	0.1132	0.107*
H19B	0.0833	−0.1921	0.0637	0.107*
H19C	0.0769	−0.1928	0.1626	0.107*
C20	0.3405 (8)	−0.2860 (4)	0.1168 (7)	0.124 (4)
H20A	0.2869	−0.3406	0.1151	0.186*
H20B	0.3938	−0.2869	0.1668	0.186*
H20C	0.3960	−0.2843	0.0678	0.186*
Cl1	0.69430 (16)	−0.13510 (9)	0.11283 (9)	0.0669 (4)
Cl2	0.78812 (13)	0.12033 (10)	0.13306 (9)	0.0600 (3)
N1	0.2599 (4)	0.1427 (2)	0.2286 (2)	0.0374 (8)
N2	0.2542 (4)	0.1530 (2)	0.0338 (2)	0.0351 (7)
N3	0.2569 (4)	−0.2042 (2)	0.1178 (3)	0.0543 (10)
O1	0.4899 (3)	0.0332 (2)	0.20459 (17)	0.0370 (7)
O2	0.4901 (3)	0.04781 (19)	0.04569 (18)	0.0368 (7)
O3	0.2441 (3)	−0.04817 (17)	0.1202 (2)	0.0384 (6)
Zn1	0.33938 (4)	0.07588 (3)	0.12725 (3)	0.03059 (13)
Zn2	0.63601 (4)	0.01228 (3)	0.12336 (3)	0.03427 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0287 (19)	0.0336 (18)	0.0303 (17)	−0.0038 (17)	0.0000 (15)	0.0002 (15)
C2	0.043 (3)	0.051 (3)	0.041 (2)	0.010 (2)	0.006 (2)	0.006 (2)
C3	0.053 (3)	0.056 (3)	0.036 (2)	0.007 (3)	0.000 (2)	0.010 (2)
C4	0.060 (3)	0.059 (3)	0.0282 (19)	0.004 (3)	−0.0008 (19)	0.007 (2)
C5	0.048 (3)	0.053 (3)	0.0350 (19)	−0.004 (2)	0.0064 (19)	−0.0060 (19)
C6	0.032 (2)	0.036 (2)	0.0344 (17)	−0.0022 (18)	−0.0021 (16)	−0.0015 (16)
C7	0.036 (2)	0.041 (2)	0.044 (2)	0.0022 (18)	0.0056 (17)	−0.0122 (18)
C8	0.045 (3)	0.055 (3)	0.055 (2)	0.026 (2)	0.003 (2)	−0.010 (2)
C9	0.050 (3)	0.036 (2)	0.084 (3)	0.014 (2)	−0.004 (3)	−0.002 (2)
C10	0.050 (3)	0.055 (3)	0.054 (2)	0.026 (3)	0.003 (2)	0.011 (2)
C11	0.0316 (19)	0.038 (2)	0.045 (2)	0.0069 (17)	−0.0046 (17)	0.0119 (17)
C12	0.030 (2)	0.034 (2)	0.0332 (17)	−0.0028 (18)	−0.0025 (15)	0.0047 (15)
C13	0.039 (2)	0.053 (3)	0.0369 (19)	−0.007 (2)	−0.0097 (18)	0.006 (2)
C14	0.049 (3)	0.048 (2)	0.033 (2)	−0.008 (2)	−0.0027 (19)	−0.0041 (18)
C15	0.051 (3)	0.047 (3)	0.043 (2)	0.000 (3)	0.010 (2)	−0.006 (2)
C16	0.044 (3)	0.038 (2)	0.0346 (19)	0.007 (2)	0.0046 (18)	0.0015 (18)
C17	0.038 (2)	0.0274 (17)	0.0307 (18)	−0.0071 (17)	0.0006 (16)	0.0018 (14)
C18	0.042 (2)	0.0305 (19)	0.057 (2)	−0.0003 (16)	0.000 (2)	0.0007 (19)
C19	0.059 (3)	0.049 (3)	0.105 (5)	−0.017 (3)	0.006 (4)	−0.003 (3)
C20	0.076 (4)	0.033 (3)	0.263 (12)	0.014 (3)	0.025 (8)	0.001 (5)
Cl1	0.0836 (10)	0.0468 (6)	0.0704 (8)	0.0303 (7)	0.0038 (7)	0.0035 (6)
Cl2	0.0500 (6)	0.0674 (8)	0.0625 (7)	−0.0143 (6)	−0.0067 (6)	0.0113 (7)
N1	0.0366 (19)	0.0350 (16)	0.0406 (17)	0.0081 (16)	0.0002 (15)	−0.0058 (14)
N2	0.0319 (18)	0.0332 (16)	0.0403 (17)	0.0070 (15)	0.0003 (14)	0.0063 (13)
N3	0.050 (2)	0.0316 (16)	0.081 (3)	−0.0004 (16)	0.001 (3)	−0.004 (2)
O1	0.0321 (15)	0.0494 (16)	0.0296 (13)	0.0113 (14)	0.0000 (11)	0.0005 (11)
O2	0.0350 (16)	0.0441 (15)	0.0312 (13)	0.0109 (14)	−0.0022 (11)	0.0031 (11)
O3	0.0378 (14)	0.0308 (12)	0.0466 (15)	0.0009 (11)	0.0004 (15)	0.0008 (13)
Zn1	0.0315 (2)	0.0277 (2)	0.0325 (2)	0.00666 (16)	0.0005 (2)	0.00044 (18)
Zn2	0.0304 (2)	0.0392 (2)	0.0332 (2)	0.00806 (17)	0.0015 (2)	0.0034 (2)

Geometric parameters (Å, º) top

Zn1—Zn2	3.161 (1)	C13—C14	1.366 (7)
C1—O1	1.334 (4)	C13—H13	0.9300
C1—C6	1.390 (6)	C14—C15	1.382 (7)
C1—C2	1.398 (6)	C14—H14	0.9300
C2—C3	1.381 (6)	C15—C16	1.378 (6)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.377 (7)	C16—C17	1.410 (6)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.379 (7)	C17—O2	1.330 (5)
C4—H4	0.9300	C18—O3	1.234 (5)
C5—C6	1.409 (5)	C18—N3	1.314 (5)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.442 (6)	C19—N3	1.435 (7)
C7—N1	1.289 (5)	C19—H19A	0.9600
C7—H7	0.9300	C19—H19B	0.9600
C8—C9	1.476 (7)	C19—H19C	0.9600
C8—N1	1.491 (6)	C20—N3	1.456 (7)
C8—H8A	0.9700	C20—H20A	0.9600
C8—H8B	0.9700	C20—H20B	0.9600
C9—C10	1.511 (7)	C20—H20C	0.9600
C9—H9A	0.9700	Cl1—Zn2	2.2163 (14)
C9—H9B	0.9700	Cl2—Zn2	2.2054 (14)
C10—N2	1.470 (6)	N1—Zn1	2.040 (3)
C10—H10A	0.9700	N2—Zn1	2.046 (3)
C10—H10B	0.9700	O1—Zn2	1.991 (3)
C11—N2	1.276 (5)	O1—Zn1	2.058 (3)
C11—C12	1.441 (6)	O2—Zn2	1.997 (3)
C11—H11	0.9300	O2—Zn1	2.048 (3)
C12—C17	1.408 (6)	O3—Zn1	2.041 (3)
C12—C13	1.406 (5)

O1—C1—C6	122.1 (4)	C15—C16—C17	120.9 (5)
O1—C1—C2	119.9 (4)	C15—C16—H16	119.6
C6—C1—C2	118.0 (4)	C17—C16—H16	119.6
C3—C2—C1	121.7 (5)	O2—C17—C12	121.6 (4)
C3—C2—H2	119.1	O2—C17—C16	119.8 (4)
C1—C2—H2	119.1	C12—C17—C16	118.6 (4)
C4—C3—C2	120.4 (5)	O3—C18—N3	124.8 (4)
C4—C3—H3	119.8	O3—C18—H18	117.6
C2—C3—H3	119.8	N3—C18—H18	117.6
C3—C4—C5	118.9 (4)	N3—C19—H19A	109.5
C3—C4—H4	120.5	N3—C19—H19B	109.5
C5—C4—H4	120.5	H19A—C19—H19B	109.5
C4—C5—C6	121.3 (5)	N3—C19—H19C	109.5
C4—C5—H5	119.4	H19A—C19—H19C	109.5
C6—C5—H5	119.4	H19B—C19—H19C	109.5
C1—C6—C5	119.6 (5)	N3—C20—H20A	109.5
C1—C6—C7	125.1 (4)	N3—C20—H20B	109.5
C5—C6—C7	115.3 (4)	H20A—C20—H20B	109.5
N1—C7—C6	127.4 (4)	N3—C20—H20C	109.5
N1—C7—H7	116.3	H20A—C20—H20C	109.5
C6—C7—H7	116.3	H20B—C20—H20C	109.5
C9—C8—N1	112.7 (4)	C7—N1—C8	116.1 (3)
C9—C8—H8A	109.1	C7—N1—Zn1	125.1 (3)
N1—C8—H8A	109.1	C8—N1—Zn1	118.5 (3)
C9—C8—H8B	109.1	C11—N2—C10	115.9 (4)
N1—C8—H8B	109.1	C11—N2—Zn1	124.0 (3)
H8A—C8—H8B	107.8	C10—N2—Zn1	119.8 (3)
C8—C9—C10	115.9 (4)	C18—N3—C19	122.4 (4)
C8—C9—H9A	108.3	C18—N3—C20	120.8 (5)
C10—C9—H9A	108.3	C19—N3—C20	116.7 (5)
C8—C9—H9B	108.3	C1—O1—Zn2	130.5 (2)
C10—C9—H9B	108.3	C1—O1—Zn1	126.9 (2)
H9A—C9—H9B	107.4	Zn2—O1—Zn1	102.65 (12)
N2—C10—C9	112.3 (4)	C17—O2—Zn2	130.5 (3)
N2—C10—H10A	109.1	C17—O2—Zn1	126.0 (3)
C9—C10—H10A	109.1	Zn2—O2—Zn1	102.79 (13)
N2—C10—H10B	109.1	C18—O3—Zn1	119.6 (3)
C9—C10—H10B	109.1	O3—Zn1—N1	105.60 (14)
H10A—C10—H10B	107.9	O3—Zn1—N2	103.66 (13)
N2—C11—C12	127.9 (4)	N1—Zn1—N2	98.22 (13)
N2—C11—H11	116.0	O3—Zn1—O2	98.58 (12)
C12—C11—H11	116.0	N1—Zn1—O2	152.58 (14)
C17—C12—C13	118.1 (5)	N2—Zn1—O2	88.28 (12)
C17—C12—C11	124.5 (4)	O3—Zn1—O1	97.17 (12)
C13—C12—C11	117.3 (4)	N1—Zn1—O1	88.27 (13)
C14—C13—C12	122.7 (5)	N2—Zn1—O1	155.53 (13)
C14—C13—H13	118.7	O2—Zn1—O1	75.90 (10)
C12—C13—H13	118.7	O1—Zn2—O2	78.56 (10)
C13—C14—C15	118.9 (4)	O1—Zn2—Cl2	111.93 (10)
C13—C14—H14	120.5	O2—Zn2—Cl2	112.63 (9)
C15—C14—H14	120.5	O1—Zn2—Cl1	113.28 (10)
C14—C15—C16	120.8 (5)	O2—Zn2—Cl1	113.59 (9)
C14—C15—H15	119.6	Cl2—Zn2—Cl1	119.75 (7)
C16—C15—H15	119.6

O1—C1—C2—C3	176.7 (5)	C18—O3—Zn1—N2	132.1 (4)
C6—C1—C2—C3	−1.6 (8)	C18—O3—Zn1—O2	41.8 (4)
C1—C2—C3—C4	0.5 (9)	C18—O3—Zn1—O1	−34.9 (4)
C2—C3—C4—C5	0.9 (9)	C7—N1—Zn1—O3	80.9 (4)
C3—C4—C5—C6	−1.2 (8)	C8—N1—Zn1—O3	−92.9 (3)
O1—C1—C6—C5	−177.0 (4)	C7—N1—Zn1—N2	−172.4 (4)
C2—C1—C6—C5	1.3 (7)	C8—N1—Zn1—N2	13.8 (3)
O1—C1—C6—C7	1.0 (7)	C7—N1—Zn1—O2	−70.1 (5)
C2—C1—C6—C7	179.2 (4)	C8—N1—Zn1—O2	116.1 (4)
C4—C5—C6—C1	0.1 (8)	C7—N1—Zn1—O1	−16.1 (4)
C4—C5—C6—C7	−178.0 (4)	C8—N1—Zn1—O1	170.1 (3)
C1—C6—C7—N1	8.3 (7)	C11—N2—Zn1—O3	−77.4 (4)
C5—C6—C7—N1	−173.6 (5)	C10—N2—Zn1—O3	95.2 (3)
N1—C8—C9—C10	74.7 (6)	C11—N2—Zn1—N1	174.2 (4)
C8—C9—C10—N2	−73.1 (6)	C10—N2—Zn1—N1	−13.2 (3)
N2—C11—C12—C17	−10.6 (8)	C11—N2—Zn1—O2	21.0 (4)
N2—C11—C12—C13	172.4 (5)	C10—N2—Zn1—O2	−166.4 (3)
C17—C12—C13—C14	1.9 (8)	C11—N2—Zn1—O1	70.1 (5)
C11—C12—C13—C14	179.2 (4)	C10—N2—Zn1—O1	−117.3 (4)
C12—C13—C14—C15	−1.0 (8)	C17—O2—Zn1—O3	73.2 (3)
C13—C14—C15—C16	0.1 (8)	Zn2—O2—Zn1—O3	−97.72 (13)
C14—C15—C16—C17	−0.2 (9)	C17—O2—Zn1—N1	−134.9 (3)
C13—C12—C17—O2	178.1 (4)	Zn2—O2—Zn1—N1	54.1 (3)
C11—C12—C17—O2	1.1 (7)	C17—O2—Zn1—N2	−30.3 (3)
C13—C12—C17—C16	−2.0 (6)	Zn2—O2—Zn1—N2	158.72 (14)
C11—C12—C17—C16	−179.0 (4)	C17—O2—Zn1—O1	168.5 (3)
C15—C16—C17—O2	−178.9 (5)	Zn2—O2—Zn1—O1	−2.43 (11)
C15—C16—C17—C12	1.2 (7)	C1—O1—Zn1—O3	−80.4 (3)
C6—C7—N1—C8	178.2 (4)	Zn2—O1—Zn1—O3	99.53 (14)
C6—C7—N1—Zn1	4.3 (7)	C1—O1—Zn1—N1	25.1 (3)
C9—C8—N1—C7	144.1 (4)	Zn2—O1—Zn1—N1	−154.96 (15)
C9—C8—N1—Zn1	−41.5 (5)	C1—O1—Zn1—N2	131.3 (4)
C12—C11—N2—C10	−179.5 (4)	Zn2—O1—Zn1—N2	−48.8 (3)
C12—C11—N2—Zn1	−6.6 (7)	C1—O1—Zn1—O2	−177.5 (4)
C9—C10—N2—C11	−147.9 (4)	Zn2—O1—Zn1—O2	2.44 (11)
C9—C10—N2—Zn1	38.9 (5)	C1—O1—Zn2—O2	177.5 (4)
O3—C18—N3—C19	1.2 (9)	Zn1—O1—Zn2—O2	−2.47 (12)
O3—C18—N3—C20	179.5 (7)	C1—O1—Zn2—Cl2	−72.6 (4)
C6—C1—O1—Zn2	158.5 (3)	Zn1—O1—Zn2—Cl2	107.51 (11)
C2—C1—O1—Zn2	−19.7 (6)	C1—O1—Zn2—Cl1	66.5 (4)
C6—C1—O1—Zn1	−21.6 (6)	Zn1—O1—Zn2—Cl1	−113.41 (11)
C2—C1—O1—Zn1	160.2 (3)	C17—O2—Zn2—O1	−167.9 (3)
C12—C17—O2—Zn2	−167.5 (3)	Zn1—O2—Zn2—O1	2.48 (12)
C16—C17—O2—Zn2	12.6 (6)	C17—O2—Zn2—Cl2	82.9 (3)
C12—C17—O2—Zn1	24.1 (5)	Zn1—O2—Zn2—Cl2	−106.69 (11)
C16—C17—O2—Zn1	−155.8 (3)	C17—O2—Zn2—Cl1	−57.3 (3)
N3—C18—O3—Zn1	178.2 (4)	Zn1—O2—Zn2—Cl1	113.07 (10)
C18—O3—Zn1—N1	−125.1 (4)

Experimental details

Crystal data
Chemical formula	[Zn₂Cl₂(C₁₇H₁₆N₂O₂)(C₃H₇NO)]
M_r	555.09
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	10.1959 (9), 14.443 (3), 15.8359 (15)
V (Å³)	2332.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.31
Crystal size (mm)	0.40 × 0.40 × 0.40

Data collection
Diffractometer	Enraf Nonius CAD4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.383, 0.397
No. of measured, independent and observed [I > 2σ(I)] reflections	2929, 2927, 2718
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.642

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.090, 1.11
No. of reflections	2927
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.41
Absolute structure	(Flack, 1983), no Friedel pairs
Absolute structure parameter	−0.01 (2)

Computer programs: CAD-4 EXPRESS (Enraf Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Zn1—Zn2	3.161 (1)	O1—Zn2	1.991 (3)
Cl1—Zn2	2.2163 (14)	O1—Zn1	2.058 (3)
Cl2—Zn2	2.2054 (14)	O2—Zn2	1.997 (3)
N1—Zn1	2.040 (3)	O2—Zn1	2.048 (3)
N2—Zn1	2.046 (3)	O3—Zn1	2.041 (3)

C7—N1—Zn1	125.1 (3)	O3—Zn1—O2	98.58 (12)
C8—N1—Zn1	118.5 (3)	N1—Zn1—O2	152.58 (14)
C11—N2—Zn1	124.0 (3)	N2—Zn1—O2	88.28 (12)
C10—N2—Zn1	119.8 (3)	O3—Zn1—O1	97.17 (12)
C1—O1—Zn2	130.5 (2)	N1—Zn1—O1	88.27 (13)
C1—O1—Zn1	126.9 (2)	N2—Zn1—O1	155.53 (13)
Zn2—O1—Zn1	102.65 (12)	O2—Zn1—O1	75.90 (10)
C17—O2—Zn2	130.5 (3)	O1—Zn2—O2	78.56 (10)
C17—O2—Zn1	126.0 (3)	O1—Zn2—Cl2	111.93 (10)
Zn2—O2—Zn1	102.79 (13)	O2—Zn2—Cl2	112.63 (9)
C18—O3—Zn1	119.6 (3)	O1—Zn2—Cl1	113.28 (10)
O3—Zn1—N1	105.60 (14)	O2—Zn2—Cl1	113.59 (9)
O3—Zn1—N2	103.66 (13)	Cl2—Zn2—Cl1	119.75 (7)
N1—Zn1—N2	98.22 (13)

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{[μ-N,N′-Bis­(salicyl­idene)-1,3-propane­diaminato-N,N′-di­methyl­form­amide]­zinc(II)}di­chlorozinc(II)

Supporting information

Key indicators

checkCIF results

{[μ-N,N′-Bis(salicylidene)-1,3-propanediaminato-N,N′-dimethylformamide]zinc(II)}dichlorozinc(II)