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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): m1211–m1212.
Published online 2008 August 30. doi:  10.1107/S1600536808027104
PMCID: PMC2960607

Dichlorido(5,5′-dimethyl-2,2′-bipyridine-κ2 N,N′)zinc(II)

Abstract

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(...)π contacts between the methyl groups and the pyridine and five-membered rings containing ZnII atoms; π–π contacts also exist between the pyridine rings [centroid–centroid distances = 3.665 (5) and 3.674 (5) Å].

Related literature

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

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Object name is e-64-m1211-scheme1.jpg

Experimental

Crystal data

  • [ZnCl2(C12H12N2)]
  • M r = 320.53
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1211-efi1.jpg
  • a = 16.267 (2) Å
  • b = 11.1704 (16) Å
  • c = 14.9328 (14) Å
  • V = 2713.4 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 2.18 mm−1
  • T = 298 (2) K
  • 0.28 × 0.20 × 0.07 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1998 [triangle]) T min = 0.612, T max = 0.860
  • 14309 measured reflections
  • 7167 independent reflections
  • 4463 reflections with I > 2σ(I)
  • R int = 0.066

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.150
  • S = 1.07
  • 7167 reflections
  • 307 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.30 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 3320 Friedel pairs
  • Flack parameter: 0.07 (3)

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

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027104/hk2517sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027104/hk2517Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
Fig. 2.
A packing diagram of the title compound.

Crystal data

[ZnCl2(C12H12N2)]F000 = 1296
Mr = 320.53Dx = 1.569 Mg m3
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 mm1
c = 14.9328 (14) ÅT = 298 (2) K
V = 2713.4 (6) Å3Block, colorless
Z = 80.28 × 0.20 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer7167 independent reflections
Radiation source: fine-focus sealed tube4463 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.066
T = 298(2) Kθmax = 29.3º
[var phi] 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

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 Å3
7167 reflectionsΔρmin = −0.30 e Å3
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

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2517).

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