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Acta Cryst. (2008). E64, m1211-m1212    [ doi:10.1107/S1600536808027104 ]

Dichlorido(5,5'-dimethyl-2,2'-bipyridine-[kappa]2N,N')zinc(II)

A. Khalighi, R. Ahmadi, V. Amani and H. R. Khavasi

Abstract top

The asymmetric unit of the title compound, [ZnCl2(C12H12N2)], contains two independent molecules. The ZnII atoms are four-coordinated in distorted tetrahedral configurations by two N atoms from 5,5'-dimethyl-2,2'-bipyridine and two terminal Cl atoms. In the crystal structure, intermolecular C-H...Cl hydrogen bonds link the molecules. There are C-H...[pi] contacts between the methyl groups and the pyridine and five-membered rings containing ZnII atoms; [pi]-[pi] contacts also exist between the pyridine rings [centroid-centroid distances = 3.665 (5) and 3.674 (5) Å].

Comment top

There are several ZnII complexes, with formula, [ZnCl2(N—N)], such as [ZnCl2(bipy)], (II), (Khan & Tuck, 1984), [ZnCl2(biim)], (III), (Gruia et al., 2007), [ZnCl2(phbipy)], (IV), (Kozhevnikov et al., 2006), [ZnCl2(phen)], (V), (Reimann et al., 1966), [ZnCl2(dmphen)], (VI), (Preston & Kennard, 1969), [ZnCl2(dpdmbip)], (VII), (Liu et al., 2004) and [ZnCl2(dm4bt)], (VIII), (Khavasi et al., 2008) [where bipy is 2,2'-bipyridine, biim is 2,2'-biimidazole, phbipy is 5-phenyl-2,2'-bi- pyridine, phen is 1,10-phenanthroline, dmphen is 2,9-dimethyl-1,10-phenanthro- line, dpdmbip is 4,4'-diphenyl-6,6'-dimethyl-2,2'-bipyrimidine and dm4bt is 2,2'-dimethyl-4,4'-bithiazole] have been synthesized and characterized by single-crystal X-ray diffraction methods. There are also several ZnII complexes, with formula, [ZnCl2L2], such as [ZnCl2(py)2], (IX), (Steffen & Palenik, 1976), [ZnCl2(4-cypy)2], (X), (Steffen & Palenik, 1977), [ZnCl2(2-ampy)2], (XI), (Qin et al., 1999) and [ZnCl2(im)2], (XII), (Lundberg, 1966), [where py is pyridine, 4-cypy is 4-cyanopyridine, 2-ampy is 2-aminopyridine and im is imidazole] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

The asymmetric unit of (I), (Fig. 1), contains two independent molecules. The ZnII atoms are four-coordinated in distorted tetrahedral configurations (Table 1) by two N atoms from 5,5'-dimethyl-2,2'-bipyridine and two terminal Cl. The Zn-Cl and Zn-N bond lengths and angles (Table 1) are within normal ranges, as in (II), (V) and (VIII).

In the crystal structure, intermolecular C-H···Cl hydrogen bonds (Table 2) link the molecules, in which they may be effective in the stabilization of the structure. There also exist C—H···π contacts (Table 1) between the methyl groups and pyridine, (Zn1/N1/N2/C6/C7) and (Zn2/N3/N4/C18/C19) rings. The π—π contacts between the pyridine rings, Cg3···Cg6i and Cg4···Cg5ii [symmetry codes: (i) x, y, z; (ii) x, 1 + y, z, where Cg3, Cg4, Cg5 and Cg6 are centroids of the rings (N1/C1/C2/C4-C6), (N2/C7-C10/C12), (N3/C13/C14/C16-C18) and (N4/C19-C22/C24), respectively] further stabilize the structure, with centroid-centroid distances of 3.665 (5) and 3.674 (5) Å, respectively.

Related literature top

For related literature, see: Gruia et al. (2007); Khan & Tuck (1984); Khavasi et al. (2008); Kozhevnikov et al. (2006); Liu et al. (2004); Lundberg (1966); Preston & Kennard (1969); Qin et al. (1999); Reimann et al. (1966); Steffen & Palenik (1976, 1977).

Experimental top

For the preparation of the title compound, a solution of 5,5'-dimethyl-2,2' -bipyridine (0.25 g, 1.33 mmol) in methanol (100 ml) was added to a solution of ZnCl2 (0.18 g, 1.33 mmol) in methanol (100 ml) and the resulting colorless solution was stirred for 5 min at room temperature, and then left to evaporate slowly at room temperature. After one week, colorless block crystals of the title compound were isolated (yield; 0.32 g, 73.4%, m.p. < 573 K).

Refinement top

H atoms were positioned geometrically, with C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
[Figure 2] Fig. 2. A packing diagram of the title compound.
Dichlorido(5,5'-dimethyl-2,2'-bipyridine-κ2N,N')zinc(II) top
Crystal data top
[ZnCl2(C12H12N2)]F000 = 1296
Mr = 320.53Dx = 1.569 Mg m−3
Orthorhombic, Pna21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 2610 reflections
a = 16.267 (2) Åθ = 2.2–29.3º
b = 11.1704 (16) ŵ = 2.18 mm−1
c = 14.9328 (14) ÅT = 298 (2) K
V = 2713.4 (6) Å3Block, colorless
Z = 80.28 × 0.20 × 0.07 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		7167 independent reflections
Radiation source: fine-focus sealed tube4463 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.066
T = 298(2) Kθmax = 29.3º
φ and ω scansθmin = 2.2º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)		h = −22→13
Tmin = 0.612, Tmax = 0.860k = −13→15
14309 measured reflectionsl = −20→20
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.066  w = 1/[σ2(Fo2) + (0.0545P)2 + 2.0209P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.150(Δ/σ)max = 0.045
S = 1.08Δρmax = 0.29 e Å−3
7167 reflectionsΔρmin = −0.30 e Å−3
307 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 3320 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.07 (3)
Secondary atom site location: difference Fourier map
Crystal data top
[ZnCl2(C12H12N2)]V = 2713.4 (6) Å3
Mr = 320.53Z = 8
Orthorhombic, Pna21Mo Kα
a = 16.267 (2) ŵ = 2.18 mm−1
b = 11.1704 (16) ÅT = 298 (2) K
c = 14.9328 (14) Å0.28 × 0.20 × 0.07 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		7167 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)		4463 reflections with I > 2σ(I)
Tmin = 0.612, Tmax = 0.860Rint = 0.066
14309 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.150Δρmax = 0.29 e Å−3
S = 1.08Δρmin = −0.30 e Å−3
7167 reflectionsAbsolute structure: Flack (1983), 3320 Friedel pairs
307 parametersFlack parameter: 0.07 (3)
1 restraint
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
xyzUiso*/Ueq
Zn1−0.27268 (5)−0.87606 (8)−0.43784 (5)0.0530 (4)
Zn2−0.77530 (5)−1.11325 (7)−0.47118 (5)0.0521 (3)
Cl1−0.33658 (15)−0.9839 (2)−0.33543 (19)0.0872 (8)
Cl2−0.35350 (12)−0.7899 (2)−0.53825 (16)0.0671 (6)
Cl3−0.84859 (13)−1.0208 (2)−0.36748 (16)0.0644 (6)
Cl4−0.84271 (14)−1.2264 (2)−0.56774 (19)0.0823 (8)
N1−0.1798 (4)−0.7734 (5)−0.3840 (4)0.0508 (16)
N2−0.1730 (4)−0.9564 (5)−0.4975 (4)0.0508 (15)
N3−0.6710 (4)−1.1912 (5)−0.4188 (4)0.0521 (14)
N4−0.6855 (4)−1.0095 (6)−0.5312 (5)0.0503 (15)
C1−0.1882 (5)−0.6828 (7)−0.3260 (5)0.0541 (18)
H1−0.2408−0.6608−0.30810.065*
C2−0.1206 (6)−0.6198 (7)−0.2909 (6)0.060 (2)
C3−0.1361 (7)−0.5168 (8)−0.2285 (6)0.089 (3)
H3A−0.1689−0.4576−0.25840.107*
H3B−0.0846−0.4819−0.21080.107*
H3C−0.1648−0.5449−0.17640.107*
C4−0.0441 (6)−0.6540 (9)−0.3175 (6)0.071 (2)
H40.0018−0.6146−0.29490.085*
C5−0.0340 (5)−0.7457 (9)−0.3773 (6)0.062 (2)
H50.0183−0.7674−0.39630.075*
C6−0.1031 (5)−0.8063 (7)−0.4095 (5)0.0524 (19)
C7−0.1007 (4)−0.9082 (7)−0.4741 (6)0.0459 (17)
C8−0.0275 (5)−0.9510 (8)−0.5090 (5)0.061 (2)
H80.0226−0.9168−0.49300.073*
C9−0.0309 (5)−1.0467 (9)−0.5686 (6)0.069 (3)
H90.0177−1.0773−0.59210.082*
C10−0.1045 (7)−1.0967 (8)−0.5934 (6)0.062 (3)
C11−0.1117 (7)−1.1986 (8)−0.6598 (6)0.082 (3)
H11A−0.1368−1.2664−0.63110.098*
H11B−0.0579−1.2202−0.68070.098*
H11C−0.1449−1.1739−0.70960.098*
C12−0.1746 (5)−1.0486 (7)−0.5547 (6)0.057 (2)
H12−0.2252−1.0820−0.56940.068*
C13−0.6682 (5)−1.2826 (7)−0.3606 (6)0.059 (2)
H13−0.7178−1.3166−0.34290.071*
C14−0.5966 (6)−1.3302 (9)−0.3250 (6)0.067 (2)
C15−0.5985 (7)−1.4306 (9)−0.2602 (6)0.089 (3)
H15A−0.6285−1.4068−0.20780.107*
H15B−0.5434−1.4516−0.24380.107*
H15C−0.6251−1.4985−0.28710.107*
C16−0.5243 (6)−1.2783 (9)−0.3560 (7)0.074 (3)
H16−0.4741−1.3087−0.33700.089*
C17−0.5255 (5)−1.1830 (9)−0.4141 (6)0.074 (2)
H17−0.4765−1.1473−0.43220.089*
C18−0.6005 (5)−1.1398 (8)−0.4458 (7)0.0552 (19)
C19−0.6087 (4)−1.0390 (7)−0.5074 (5)0.0501 (17)
C20−0.5433 (5)−0.9743 (9)−0.5441 (7)0.072 (3)
H20−0.4894−0.9962−0.53100.086*
C21−0.5580 (6)−0.8791 (8)−0.5990 (5)0.069 (2)
H21−0.5140−0.8339−0.61990.083*
C22−0.6369 (6)−0.8486 (7)−0.6240 (5)0.0578 (19)
C23−0.6548 (6)−0.7477 (8)−0.6847 (6)0.080 (3)
H23A−0.6848−0.7765−0.73570.096*
H23B−0.6042−0.7120−0.70420.096*
H23C−0.6871−0.6891−0.65360.096*
C24−0.6992 (5)−0.9174 (7)−0.5874 (5)0.0572 (18)
H24−0.7533−0.8990−0.60230.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0310 (4)0.0557 (5)0.0721 (10)−0.0013 (4)0.0036 (4)0.0035 (4)
Zn20.0336 (4)0.0550 (5)0.0678 (9)0.0005 (4)−0.0026 (4)−0.0006 (4)
Cl10.0615 (14)0.0871 (16)0.113 (2)0.0035 (12)0.0292 (13)0.0328 (14)
Cl20.0426 (10)0.0783 (13)0.0805 (15)0.0030 (9)−0.0096 (9)0.0048 (11)
Cl30.0490 (11)0.0682 (12)0.0759 (14)−0.0025 (9)0.0060 (9)−0.0081 (10)
Cl40.0550 (13)0.0829 (15)0.109 (2)0.0089 (11)−0.0215 (12)−0.0355 (14)
N10.038 (3)0.049 (3)0.065 (4)−0.002 (3)−0.007 (3)0.012 (3)
N20.037 (3)0.047 (3)0.069 (4)−0.003 (3)0.011 (3)0.009 (3)
N30.041 (3)0.057 (3)0.058 (4)−0.001 (3)−0.001 (3)−0.011 (3)
N40.034 (3)0.063 (4)0.055 (4)−0.002 (3)0.003 (3)−0.008 (3)
C10.045 (4)0.057 (4)0.061 (4)−0.002 (3)−0.008 (3)0.002 (3)
C20.065 (5)0.062 (5)0.053 (5)−0.006 (4)−0.016 (4)0.013 (4)
C30.135 (10)0.068 (6)0.066 (6)−0.018 (6)−0.023 (6)0.001 (4)
C40.067 (6)0.080 (6)0.066 (5)−0.028 (5)−0.016 (4)0.006 (5)
C50.035 (4)0.088 (6)0.063 (5)−0.004 (4)−0.002 (3)0.010 (5)
C60.046 (4)0.058 (4)0.054 (4)−0.010 (3)−0.005 (3)0.021 (3)
C70.027 (3)0.056 (4)0.055 (5)0.003 (3)0.007 (3)0.017 (4)
C80.046 (4)0.073 (5)0.065 (5)0.012 (4)0.008 (3)0.014 (4)
C90.051 (5)0.093 (7)0.062 (5)0.025 (5)0.021 (4)0.027 (5)
C100.081 (7)0.057 (4)0.048 (5)0.023 (5)0.013 (4)0.022 (4)
C110.102 (8)0.073 (6)0.071 (6)0.026 (5)0.017 (5)0.005 (5)
C120.041 (4)0.059 (5)0.071 (5)−0.002 (3)0.000 (3)0.017 (4)
C130.058 (5)0.056 (5)0.064 (5)0.001 (4)−0.009 (4)−0.008 (4)
C140.069 (6)0.070 (5)0.061 (5)0.029 (5)−0.013 (4)−0.019 (4)
C150.112 (9)0.082 (7)0.073 (6)0.028 (6)−0.029 (6)−0.006 (5)
C160.052 (5)0.093 (7)0.078 (6)0.032 (5)−0.014 (4)−0.013 (5)
C170.037 (4)0.098 (7)0.089 (6)0.006 (4)−0.012 (4)−0.016 (5)
C180.048 (4)0.059 (4)0.058 (5)0.008 (4)0.010 (4)−0.020 (4)
C190.033 (3)0.068 (4)0.049 (4)0.001 (3)0.002 (3)−0.018 (3)
C200.039 (4)0.098 (7)0.078 (6)−0.011 (4)0.005 (4)−0.032 (5)
C210.078 (6)0.076 (6)0.053 (5)−0.021 (5)0.005 (4)−0.006 (4)
C220.077 (6)0.054 (4)0.042 (4)−0.005 (4)0.008 (3)−0.008 (3)
C230.093 (7)0.076 (6)0.071 (6)−0.018 (5)0.013 (5)−0.007 (5)
C240.050 (4)0.066 (5)0.055 (4)0.005 (4)0.002 (3)−0.002 (4)
Geometric parameters (Å, °) top
Zn1—Cl12.206 (2)C11—H11B0.9600
Zn1—Cl22.215 (2)C11—H11C0.9600
Zn2—Cl32.211 (2)C12—N21.338 (10)
Zn2—Cl42.207 (3)C12—H120.9300
Zn1—N12.058 (6)C13—N31.341 (10)
Zn1—N22.057 (6)C13—C141.386 (11)
Zn2—N32.063 (6)C13—H130.9300
Zn2—N42.066 (6)C14—C161.389 (13)
C1—N11.339 (10)C14—C151.482 (13)
C1—C21.406 (12)C15—H15A0.9600
C1—H10.9300C15—H15B0.9600
C2—C41.362 (14)C15—H15C0.9600
C2—C31.502 (12)C16—C171.374 (13)
C3—H3A0.9600C16—H160.9300
C3—H3B0.9600C17—C181.397 (11)
C3—H3C0.9600C17—H170.9300
C4—C51.369 (13)C18—N31.343 (10)
C4—H40.9300C18—C191.460 (12)
C5—C61.396 (11)C19—N41.341 (9)
C5—H50.9300C19—C201.397 (11)
C6—N11.357 (10)C20—C211.364 (13)
C6—C71.491 (11)C20—H200.9300
C7—N21.339 (9)C21—C221.379 (14)
C7—C81.387 (10)C21—H210.9300
C8—C91.392 (12)C22—C241.384 (12)
C8—H80.9300C22—C231.476 (12)
C9—C101.372 (14)C23—H23A0.9600
C9—H90.9300C23—H23B0.9600
C10—C121.386 (13)C23—H23C0.9600
C10—C111.514 (13)C24—N41.348 (10)
C11—H11A0.9600C24—H240.9300
N1—Zn1—N280.5 (2)N3—C13—C14124.8 (8)
N1—Zn1—Cl1112.2 (2)N3—C13—H13117.6
N1—Zn1—Cl2117.23 (18)C14—C13—H13117.6
N2—Zn1—Cl1115.64 (18)C13—C14—C16115.0 (9)
N2—Zn1—Cl2111.4 (2)C13—C14—C15121.6 (9)
Cl1—Zn1—Cl2115.28 (10)C16—C14—C15123.4 (9)
N3—Zn2—N479.7 (3)C14—C15—H15A109.4
N3—Zn2—Cl3112.09 (18)C14—C15—H15B109.5
N3—Zn2—Cl4114.47 (17)H15A—C15—H15B109.5
N4—Zn2—Cl4112.8 (2)C14—C15—H15C109.5
N4—Zn2—Cl3115.01 (18)H15A—C15—H15C109.5
Cl4—Zn2—Cl3117.19 (9)H15B—C15—H15C109.5
N1—C1—C2122.6 (8)C17—C16—C14121.4 (8)
N1—C1—H1118.7C17—C16—H16119.3
C2—C1—H1118.7C14—C16—H16119.3
C4—C2—C1117.7 (8)C16—C17—C18119.6 (9)
C4—C2—C3123.4 (9)C16—C17—H17120.2
C1—C2—C3118.9 (9)C18—C17—H17120.2
C2—C3—H3A109.5N3—C18—C17119.7 (9)
C2—C3—H3B109.5N3—C18—C19116.2 (7)
H3A—C3—H3B109.5C17—C18—C19124.1 (8)
C2—C3—H3C109.5N4—C19—C20118.6 (8)
H3A—C3—H3C109.5N4—C19—C18116.2 (7)
H3B—C3—H3C109.5C20—C19—C18125.2 (8)
C2—C4—C5120.8 (8)C21—C20—C19120.3 (9)
C2—C4—H4119.6C21—C20—H20119.9
C5—C4—H4119.6C19—C20—H20119.9
C4—C5—C6119.4 (8)C20—C21—C22121.4 (9)
C4—C5—H5120.3C20—C21—H21119.3
C6—C5—H5120.3C22—C21—H21119.3
N1—C6—C5120.8 (8)C21—C22—C24115.9 (8)
N1—C6—C7114.4 (7)C21—C22—C23122.7 (9)
C5—C6—C7124.8 (8)C24—C22—C23121.3 (9)
N2—C7—C8121.1 (8)C22—C23—H23A109.5
N2—C7—C6116.9 (7)C22—C23—H23B109.5
C8—C7—C6122.0 (8)H23A—C23—H23B109.5
C7—C8—C9118.2 (8)C22—C23—H23C109.5
C7—C8—H8120.9H23A—C23—H23C109.5
C9—C8—H8120.9H23B—C23—H23C109.5
C10—C9—C8121.3 (8)N4—C24—C22123.2 (8)
C10—C9—H9119.4N4—C24—H24118.4
C8—C9—H9119.4C22—C24—H24118.4
C9—C10—C12116.6 (9)C1—N1—C6118.8 (7)
C9—C10—C11123.3 (9)C1—N1—Zn1126.7 (5)
C12—C10—C11120.2 (10)C6—N1—Zn1114.5 (5)
C10—C11—H11A109.4C12—N2—C7119.4 (7)
C10—C11—H11B109.5C12—N2—Zn1126.8 (5)
H11A—C11—H11B109.5C7—N2—Zn1113.8 (5)
C10—C11—H11C109.5C13—N3—C18119.4 (7)
H11A—C11—H11C109.5C13—N3—Zn2126.6 (5)
H11B—C11—H11C109.5C18—N3—Zn2114.0 (6)
N2—C12—C10123.4 (8)C19—N4—C24120.5 (7)
N2—C12—H12118.3C19—N4—Zn2114.0 (5)
C10—C12—H12118.3C24—N4—Zn2125.5 (5)
N1—C1—C2—C4−0.3 (13)N2—Zn1—N1—C1−179.1 (6)
N1—C1—C2—C3177.9 (7)Cl1—Zn1—N1—C1−65.2 (7)
C1—C2—C4—C50.8 (13)Cl2—Zn1—N1—C171.6 (7)
C3—C2—C4—C5−177.4 (9)N2—Zn1—N1—C6−1.4 (5)
C2—C4—C5—C6−1.5 (14)Cl1—Zn1—N1—C6112.5 (5)
C4—C5—C6—N11.7 (12)Cl2—Zn1—N1—C6−110.7 (5)
C4—C5—C6—C7−179.5 (8)C10—C12—N2—C7−1.2 (12)
N1—C6—C7—N2−1.5 (9)C10—C12—N2—Zn1178.9 (6)
C5—C6—C7—N2179.6 (8)C8—C7—N2—C120.8 (12)
N1—C6—C7—C8178.1 (7)C6—C7—N2—C12−179.6 (6)
C5—C6—C7—C8−0.8 (11)C8—C7—N2—Zn1−179.3 (6)
N2—C7—C8—C9−0.6 (12)C6—C7—N2—Zn10.3 (9)
C6—C7—C8—C9179.8 (7)N1—Zn1—N2—C12−179.6 (7)
C7—C8—C9—C100.8 (13)Cl1—Zn1—N2—C1270.3 (7)
C8—C9—C10—C12−1.2 (12)Cl2—Zn1—N2—C12−64.0 (7)
C8—C9—C10—C11178.3 (8)N1—Zn1—N2—C70.5 (6)
C9—C10—C12—N21.4 (12)Cl1—Zn1—N2—C7−109.6 (5)
C11—C10—C12—N2−178.1 (8)Cl2—Zn1—N2—C7116.2 (6)
N3—C13—C14—C16−1.8 (12)C14—C13—N3—C18−0.1 (12)
N3—C13—C14—C15179.3 (8)C14—C13—N3—Zn2−178.1 (6)
C13—C14—C16—C173.1 (13)C17—C18—N3—C130.8 (13)
C15—C14—C16—C17−178.1 (9)C19—C18—N3—C13−178.5 (7)
C14—C16—C17—C18−2.6 (15)C17—C18—N3—Zn2179.0 (7)
C16—C17—C18—N30.5 (15)C19—C18—N3—Zn2−0.3 (10)
C16—C17—C18—C19179.8 (8)N4—Zn2—N3—C13178.9 (7)
N3—C18—C19—N4−0.8 (11)Cl4—Zn2—N3—C13−70.6 (7)
C17—C18—C19—N4179.9 (8)Cl3—Zn2—N3—C1366.0 (6)
N3—C18—C19—C20−179.3 (7)N4—Zn2—N3—C180.8 (6)
C17—C18—C19—C201.4 (14)Cl4—Zn2—N3—C18111.3 (6)
N4—C19—C20—C213.6 (12)Cl3—Zn2—N3—C18−112.1 (6)
C18—C19—C20—C21−178.0 (8)C20—C19—N4—C24−1.7 (10)
C19—C20—C21—C22−4.0 (13)C18—C19—N4—C24179.7 (7)
C20—C21—C22—C242.4 (12)C20—C19—N4—Zn2−179.9 (6)
C20—C21—C22—C23−178.8 (8)C18—C19—N4—Zn21.5 (8)
C21—C22—C24—N4−0.5 (11)C22—C24—N4—C190.3 (11)
C23—C22—C24—N4−179.4 (7)C22—C24—N4—Zn2178.3 (5)
C2—C1—N1—C60.5 (11)N3—Zn2—N4—C19−1.3 (5)
C2—C1—N1—Zn1178.2 (6)Cl4—Zn2—N4—C19−113.6 (5)
C5—C6—N1—C1−1.2 (10)Cl3—Zn2—N4—C19108.4 (5)
C7—C6—N1—C1179.8 (6)N3—Zn2—N4—C24−179.4 (6)
C5—C6—N1—Zn1−179.1 (6)Cl4—Zn2—N4—C2468.3 (6)
C7—C6—N1—Zn11.9 (7)Cl3—Zn2—N4—C24−69.7 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C1—H1···Cl3i0.932.823.516 (8)132
C16—H16···Cl3ii0.932.833.638 (10)146
C3—H3A···Cg50.963.103.719 (6)124
C11—H11A···Cg2iii0.962.833.688 (5)150
C15—H15C···Cg1iv0.962.843.704 (6)150
C23—H23C···Cg40.963.113.690 (6)120
Symmetry codes: (i) x+1/2, −y−3/2, z; (ii) x+1/2, −y−5/2, z; (iii) x, y+1, z; (iv) x, y−1, z.
Table 1
Selected geometric parameters (Å, °) top
Zn1—Cl12.206 (2)Zn1—N12.058 (6)
Zn1—Cl22.215 (2)Zn1—N22.057 (6)
Zn2—Cl32.211 (2)Zn2—N32.063 (6)
Zn2—Cl42.207 (3)Zn2—N42.066 (6)
N1—Zn1—N280.5 (2)N3—Zn2—N479.7 (3)
N1—Zn1—Cl1112.2 (2)N3—Zn2—Cl3112.09 (18)
N1—Zn1—Cl2117.23 (18)N3—Zn2—Cl4114.47 (17)
N2—Zn1—Cl1115.64 (18)N4—Zn2—Cl4112.8 (2)
N2—Zn1—Cl2111.4 (2)N4—Zn2—Cl3115.01 (18)
Cl1—Zn1—Cl2115.28 (10)Cl4—Zn2—Cl3117.19 (9)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C1—H1···Cl3i0.932.823.516 (8)132
C16—H16···Cl3ii0.932.833.638 (10)146
C3—H3A···Cg50.963.103.719 (6)124
C11—H11A···Cg2iii0.962.833.688 (5)150
C15—H15C···Cg1iv0.962.843.704 (6)150
C23—H23C···Cg40.963.113.690 (6)120
Symmetry codes: (i) x+1/2, −y−3/2, z; (ii) x+1/2, −y−5/2, z; (iii) x, y+1, z; (iv) x, y−1, z.
Acknowledgements top

We are grateful to the Islamic Azad University, Shahr-e-Rey Branch, for financial support.

references
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