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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): m57.
Published online 2009 December 12. doi:  10.1107/S1600536809052738
PMCID: PMC2980065

[1,2-Bis(1H-benzimidazol-2-yl-κN 3)ethane]dichloridozinc(II)

Abstract

The title compound, [ZnCl2(C16H14N4)], crystallizes with two mol­ecules in the asymmetric unit. The ZnII atoms show distorted tetrahedral coordination environments. Adjacent mol­ecules are linked by N—H(...)Cl hydrogen bonds, forming a three-dimensional network.

Related literature

For the synthesis of the ligand, see: van Albada et al. (1995 [triangle]). For the zinc dichloride adduct of a similar N-heterocycle, see: Zhou et al. (2010 [triangle]).

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Object name is e-66-00m57-scheme1.jpg

Experimental

Crystal data

  • [ZnCl2(C16H14N4)]
  • M r = 398.58
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00m57-efi1.jpg
  • a = 8.0868 (4) Å
  • b = 13.8605 (8) Å
  • c = 14.8504 (8) Å
  • β = 92.664 (1)°
  • V = 1662.7 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.80 mm−1
  • T = 293 K
  • 0.48 × 0.34 × 0.30 mm

Data collection

  • Bruker SMART diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.479, T max = 0.614
  • 8555 measured reflections
  • 5820 independent reflections
  • 4956 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.077
  • S = 0.97
  • 5820 reflections
  • 415 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.30 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2049 Friedel pairs
  • Flack parameter: 0.1 (1)

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052738/bt5133sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052738/bt5133Isup2.hkl

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

Acknowledgments

We thank Guangxi Normal University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

1,4-Bis(2-benzimidazolyl)ethanebutane was synthesized by using a literature method (van Albada et al., 1995). To a solution of zinc chloride hexahydrate (0.25 g, 1 mmol) in ethanol (3 ml) was added an aqueous solution (4 ml) of the ligand (0.24 g, 1 mmol). The reactants were sealed in a 15-ml Teflon-lined, stainless-steel Parr bomb. The bomb was heated at 413 K for 3 days. The cool solution yielded single crystals in ca 30% yield.

Refinement

Hydrogen atoms were generated geometrically and were constrained to ride on their parent atoms [C–H = 0.95–0.99 Å; N–H 0.88 Å Uiso(H) = 1.2Ueq(C, N)].

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of the two independent molecules of ZnCl2(C16H14N4) at the 50% probability level; hydrogen atoms are drawn as sphere of arbitrary radius.

Crystal data

[ZnCl2(C16H14N4)]F(000) = 808
Mr = 398.58Dx = 1.592 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4769 reflections
a = 8.0868 (4) Åθ = 2.5–27.1°
b = 13.8605 (8) ŵ = 1.80 mm1
c = 14.8504 (8) ÅT = 293 K
β = 92.664 (1)°Block, colorless
V = 1662.7 (2) Å30.48 × 0.34 × 0.30 mm
Z = 4

Data collection

Bruker SMART diffractometer5820 independent reflections
Radiation source: fine-focus sealed tube4956 reflections with I > 2σ(I)
graphiteRint = 0.018
[var phi] and ω scansθmax = 27.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.479, Tmax = 0.614k = −17→13
8555 measured reflectionsl = −18→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.077w = 1/[σ2(Fo2) + (0.0406P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.002
5820 reflectionsΔρmax = 0.30 e Å3
415 parametersΔρmin = −0.30 e Å3
1 restraintAbsolute structure: Flack (1983), 2049 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.1 (1)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Zn10.24147 (5)0.50006 (3)0.64876 (2)0.03664 (11)
Zn20.19950 (5)0.65365 (3)1.15403 (2)0.03913 (11)
Cl1−0.01667 (11)0.50457 (12)0.58667 (6)0.0633 (3)
Cl20.43158 (10)0.50750 (9)0.54292 (5)0.0475 (2)
Cl30.42290 (13)0.60363 (9)1.08123 (6)0.0558 (3)
Cl4−0.01188 (12)0.67049 (9)1.05101 (6)0.0528 (3)
N10.2783 (4)0.6025 (2)0.74082 (19)0.0409 (7)
N20.2933 (4)0.6691 (3)0.8750 (2)0.0508 (8)
H20.28330.67640.93200.061*
N30.2869 (4)0.2549 (2)0.8128 (2)0.0447 (8)
H30.29320.22550.86380.054*
N40.2675 (4)0.3733 (2)0.71535 (18)0.0362 (7)
N50.1409 (4)0.5614 (3)1.25109 (18)0.0425 (8)
N60.0915 (4)0.4941 (3)1.38061 (18)0.0450 (7)
H60.07810.48831.43750.054*
N70.3232 (4)0.8927 (3)1.3116 (2)0.0423 (8)
H70.35050.91941.36230.051*
N80.2503 (4)0.7799 (2)1.21321 (19)0.0393 (7)
C10.3522 (5)0.6924 (3)0.7341 (2)0.0412 (9)
C20.4079 (5)0.7424 (3)0.6600 (3)0.0556 (11)
H2A0.40110.71540.60260.067*
C30.4724 (6)0.8320 (4)0.6743 (3)0.0649 (13)
H3A0.51240.86600.62590.078*
C40.4803 (6)0.8741 (4)0.7593 (4)0.0697 (13)
H40.52370.93590.76620.084*
C50.4259 (6)0.8269 (4)0.8327 (3)0.0627 (12)
H50.43210.85500.88970.075*
C60.3612 (5)0.7356 (3)0.8188 (3)0.0465 (10)
C70.2453 (4)0.5917 (3)0.8278 (2)0.0393 (8)
C80.1625 (5)0.5068 (3)0.8669 (2)0.0474 (9)
H8A0.06830.48930.82750.057*
H8B0.12040.52540.92450.057*
C90.2725 (5)0.4180 (3)0.8812 (2)0.0467 (10)
H9A0.38470.43940.89590.056*
H9B0.23500.38240.93270.056*
C100.2755 (4)0.3506 (3)0.8020 (2)0.0379 (8)
C110.2870 (5)0.2110 (3)0.7301 (3)0.0419 (9)
C120.2914 (5)0.1150 (3)0.7039 (3)0.0526 (11)
H120.29710.06520.74590.063*
C130.2871 (5)0.0971 (3)0.6128 (3)0.0572 (12)
H130.29040.03360.59270.069*
C140.2778 (5)0.1719 (3)0.5497 (3)0.0503 (11)
H140.27590.15690.48860.060*
C150.2714 (5)0.2670 (3)0.5756 (3)0.0460 (10)
H150.26480.31650.53330.055*
C160.2752 (4)0.2864 (3)0.6687 (2)0.0367 (8)
C170.1120 (5)0.4632 (3)1.2365 (3)0.0449 (9)
C180.1112 (6)0.4077 (4)1.1586 (3)0.0608 (12)
H180.12880.43541.10280.073*
C190.0837 (6)0.3114 (4)1.1666 (4)0.0710 (14)
H190.08320.27291.11530.085*
C200.0565 (6)0.2690 (4)1.2494 (3)0.0703 (14)
H200.04090.20261.25220.084*
C210.0520 (5)0.3218 (4)1.3262 (3)0.0625 (12)
H210.03060.29331.38120.075*
C220.0806 (5)0.4199 (3)1.3191 (3)0.0464 (10)
C230.1259 (4)0.5765 (3)1.3389 (2)0.0383 (8)
C240.1397 (4)0.6706 (3)1.3870 (2)0.0433 (9)
H24A0.12990.65881.45090.052*
H24B0.04690.71071.36690.052*
C250.3010 (5)0.7277 (3)1.3742 (2)0.0432 (9)
H25A0.33040.76171.42980.052*
H25B0.38920.68241.36340.052*
C260.2912 (4)0.7987 (3)1.2992 (2)0.0382 (8)
C270.3052 (4)0.9398 (3)1.2296 (3)0.0420 (9)
C280.3225 (5)1.0351 (3)1.2046 (3)0.0553 (11)
H280.34981.08271.24670.066*
C290.2976 (5)1.0563 (3)1.1143 (3)0.0596 (12)
H290.30901.11971.09490.071*
C300.2561 (5)0.9853 (4)1.0518 (3)0.0579 (12)
H300.24211.00230.99140.069*
C310.2346 (5)0.8899 (3)1.0759 (3)0.0486 (10)
H310.20550.84291.03340.058*
C320.2591 (4)0.8677 (3)1.1681 (2)0.0399 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0431 (2)0.0407 (2)0.02621 (18)0.0000 (2)0.00288 (14)0.00228 (18)
Zn20.0505 (2)0.0409 (3)0.02615 (18)0.0009 (2)0.00373 (15)−0.00242 (18)
Cl10.0401 (5)0.1098 (10)0.0401 (5)0.0026 (6)0.0018 (4)0.0161 (6)
Cl20.0464 (5)0.0616 (6)0.0353 (4)−0.0007 (5)0.0111 (3)0.0066 (5)
Cl30.0548 (6)0.0724 (8)0.0410 (5)0.0098 (5)0.0106 (4)−0.0068 (5)
Cl40.0539 (5)0.0680 (8)0.0358 (4)0.0051 (5)−0.0055 (4)−0.0060 (5)
N10.0497 (18)0.0401 (19)0.0331 (15)0.0015 (15)0.0033 (13)0.0006 (14)
N20.072 (2)0.045 (2)0.0350 (15)−0.0021 (18)0.0042 (14)−0.0078 (15)
N30.058 (2)0.040 (2)0.0361 (17)−0.0006 (16)0.0062 (14)0.0112 (15)
N40.0413 (16)0.0388 (19)0.0288 (15)−0.0049 (14)0.0043 (12)0.0018 (13)
N50.0490 (18)0.049 (2)0.0300 (15)−0.0036 (16)0.0049 (13)0.0002 (14)
N60.0483 (16)0.058 (2)0.0292 (14)−0.0059 (18)0.0031 (12)0.0082 (16)
N70.0390 (16)0.049 (2)0.0384 (17)0.0026 (15)0.0006 (13)−0.0096 (15)
N80.0461 (17)0.039 (2)0.0321 (16)−0.0003 (14)−0.0001 (13)−0.0041 (14)
C10.044 (2)0.039 (2)0.0410 (19)0.0053 (17)0.0052 (16)0.0032 (17)
C20.067 (3)0.048 (3)0.052 (2)0.000 (2)0.009 (2)0.007 (2)
C30.063 (3)0.051 (3)0.082 (3)0.002 (2)0.015 (2)0.020 (3)
C40.060 (3)0.047 (3)0.102 (4)−0.005 (2)0.000 (3)−0.002 (3)
C50.074 (3)0.047 (3)0.067 (3)−0.005 (2)0.002 (2)−0.011 (2)
C60.051 (2)0.043 (2)0.045 (2)0.0038 (19)0.0014 (18)−0.0025 (18)
C70.042 (2)0.041 (2)0.0351 (18)0.0051 (17)0.0059 (15)−0.0006 (16)
C80.057 (2)0.051 (2)0.0359 (17)0.000 (2)0.0175 (15)−0.007 (2)
C90.065 (3)0.050 (3)0.0254 (18)−0.007 (2)0.0020 (16)0.0026 (18)
C100.0391 (19)0.041 (2)0.0342 (19)−0.0046 (17)0.0063 (14)0.0036 (17)
C110.038 (2)0.040 (2)0.047 (2)0.0009 (17)0.0056 (16)0.0019 (18)
C120.056 (2)0.041 (3)0.061 (3)−0.002 (2)0.011 (2)0.001 (2)
C130.048 (2)0.043 (3)0.082 (3)−0.002 (2)0.010 (2)−0.014 (2)
C140.044 (2)0.055 (3)0.052 (2)0.001 (2)0.0078 (17)−0.017 (2)
C150.044 (2)0.054 (3)0.040 (2)−0.0032 (19)0.0024 (17)−0.0066 (19)
C160.0302 (17)0.042 (2)0.0384 (19)−0.0021 (16)0.0029 (14)−0.0009 (17)
C170.045 (2)0.047 (2)0.042 (2)−0.0060 (18)−0.0013 (16)−0.0003 (17)
C180.074 (3)0.062 (3)0.046 (2)−0.007 (3)0.002 (2)−0.006 (2)
C190.078 (3)0.063 (4)0.072 (3)−0.016 (3)0.005 (3)−0.019 (3)
C200.067 (3)0.052 (3)0.091 (4)−0.011 (2)−0.002 (3)−0.007 (3)
C210.056 (3)0.062 (3)0.069 (3)−0.010 (2)0.000 (2)0.017 (3)
C220.039 (2)0.054 (3)0.046 (2)−0.0055 (19)−0.0032 (16)0.000 (2)
C230.0337 (18)0.051 (2)0.0306 (18)0.0035 (17)0.0015 (14)0.0039 (16)
C240.0468 (19)0.057 (3)0.0269 (16)0.0026 (19)0.0077 (14)−0.0013 (17)
C250.045 (2)0.053 (3)0.0311 (18)−0.0007 (18)−0.0024 (15)−0.0045 (18)
C260.0343 (18)0.043 (2)0.038 (2)0.0007 (16)0.0065 (15)−0.0086 (17)
C270.035 (2)0.043 (3)0.048 (2)0.0037 (17)0.0050 (16)−0.0049 (19)
C280.048 (2)0.039 (3)0.078 (3)−0.0045 (19)−0.004 (2)−0.006 (2)
C290.054 (3)0.039 (3)0.085 (3)0.001 (2)0.008 (2)0.014 (3)
C300.057 (2)0.053 (3)0.064 (3)0.007 (2)0.003 (2)0.017 (2)
C310.050 (2)0.051 (3)0.044 (2)−0.001 (2)0.0029 (17)0.0048 (19)
C320.0368 (19)0.037 (2)0.046 (2)0.0034 (17)0.0072 (16)−0.0038 (18)

Geometric parameters (Å, °)

Zn1—N11.984 (3)C8—H8B0.9700
Zn1—N42.023 (3)C9—C101.503 (5)
Zn1—Cl12.243 (1)C9—H9A0.9700
Zn1—Cl22.252 (1)C9—H9B0.9700
Zn2—N52.000 (3)C11—C121.386 (6)
Zn2—N81.992 (3)C11—C161.387 (5)
Zn2—Cl32.257 (1)C12—C131.374 (6)
Zn2—Cl42.253 (1)C12—H120.9300
N1—C71.339 (4)C13—C141.397 (6)
N1—C11.388 (5)C13—H130.9300
N2—C71.330 (5)C14—C151.375 (6)
N2—C61.375 (5)C14—H140.9300
N2—H20.8600C15—C161.409 (5)
N3—C101.339 (5)C15—H150.9300
N3—C111.370 (5)C17—C181.390 (6)
N3—H30.8600C17—C221.399 (6)
N4—C101.323 (4)C18—C191.358 (7)
N4—C161.392 (5)C18—H180.9300
N5—C231.332 (4)C19—C201.390 (7)
N5—C171.397 (5)C19—H190.9300
N6—C231.334 (5)C20—C211.357 (7)
N6—C221.375 (5)C20—H200.9300
N6—H60.8600C21—C221.385 (6)
N7—C261.338 (5)C21—H210.9300
N7—C271.384 (5)C23—C241.489 (6)
N7—H70.8600C24—C251.545 (5)
N8—C261.331 (4)C24—H24A0.9700
N8—C321.392 (5)C24—H24B0.9700
C1—C61.392 (5)C25—C261.486 (6)
C1—C21.393 (5)C25—H25A0.9700
C2—C31.359 (7)C25—H25B0.9700
C2—H2A0.9300C27—C281.380 (6)
C3—C41.390 (7)C27—C321.393 (5)
C3—H3A0.9300C28—C291.378 (6)
C4—C51.361 (7)C28—H280.9300
C4—H40.9300C29—C301.383 (7)
C5—C61.382 (6)C29—H290.9300
C5—H50.9300C30—C311.382 (6)
C7—C81.485 (6)C30—H300.9300
C8—C91.527 (6)C31—C321.408 (5)
C8—H8A0.9700C31—H310.9300
N1—Zn1—N4106.03 (12)N3—C11—C12132.8 (4)
N1—Zn1—Cl1111.74 (10)N3—C11—C16104.5 (3)
N4—Zn1—Cl1107.38 (9)C12—C11—C16122.7 (4)
N1—Zn1—Cl2111.27 (10)C13—C12—C11116.7 (4)
N4—Zn1—Cl2108.80 (9)C13—C12—H12121.6
Cl1—Zn1—Cl2111.37 (3)C11—C12—H12121.6
N8—Zn2—N5107.11 (12)C12—C13—C14121.6 (4)
N8—Zn2—Cl4110.05 (9)C12—C13—H13119.2
N5—Zn2—Cl4110.98 (10)C14—C13—H13119.2
N8—Zn2—Cl3109.15 (9)C15—C14—C13121.7 (4)
N5—Zn2—Cl3111.76 (10)C15—C14—H14119.1
Cl4—Zn2—Cl3107.79 (4)C13—C14—H14119.1
C7—N1—C1106.0 (3)C14—C15—C16117.2 (4)
C7—N1—Zn1123.7 (3)C14—C15—H15121.4
C1—N1—Zn1130.1 (2)C16—C15—H15121.4
C7—N2—C6109.6 (3)C11—C16—N4109.2 (3)
C7—N2—H2125.2C11—C16—C15120.0 (4)
C6—N2—H2125.2N4—C16—C15130.8 (4)
C10—N3—C11109.7 (3)C18—C17—N5131.6 (4)
C10—N3—H3125.2C18—C17—C22119.9 (4)
C11—N3—H3125.2N5—C17—C22108.5 (4)
C10—N4—C16106.1 (3)C19—C18—C17117.7 (5)
C10—N4—Zn1132.9 (3)C19—C18—H18121.1
C16—N4—Zn1121.0 (2)C17—C18—H18121.1
C23—N5—C17106.4 (3)C18—C19—C20121.8 (5)
C23—N5—Zn2129.9 (3)C18—C19—H19119.1
C17—N5—Zn2123.7 (3)C20—C19—H19119.1
C23—N6—C22109.9 (3)C21—C20—C19121.9 (5)
C23—N6—H6125.1C21—C20—H20119.1
C22—N6—H6125.1C19—C20—H20119.1
C26—N7—C27109.1 (3)C20—C21—C22117.0 (5)
C26—N7—H7125.5C20—C21—H21121.5
C27—N7—H7125.5C22—C21—H21121.5
C26—N8—C32105.9 (3)N6—C22—C21133.6 (4)
C26—N8—Zn2129.3 (3)N6—C22—C17104.7 (4)
C32—N8—Zn2124.7 (2)C21—C22—C17121.7 (4)
N1—C1—C6109.0 (3)N5—C23—N6110.5 (4)
N1—C1—C2131.2 (4)N5—C23—C24126.8 (4)
C6—C1—C2119.7 (4)N6—C23—C24122.7 (3)
C3—C2—C1117.8 (4)C23—C24—C25115.8 (3)
C3—C2—H2A121.1C23—C24—H24A108.3
C1—C2—H2A121.1C25—C24—H24A108.3
C2—C3—C4121.8 (4)C23—C24—H24B108.3
C2—C3—H3A119.1C25—C24—H24B108.3
C4—C3—H3A119.1H24A—C24—H24B107.4
C5—C4—C3121.6 (5)C26—C25—C24114.6 (3)
C5—C4—H4119.2C26—C25—H25A108.6
C3—C4—H4119.2C24—C25—H25A108.6
C4—C5—C6117.0 (4)C26—C25—H25B108.6
C4—C5—H5121.5C24—C25—H25B108.6
C6—C5—H5121.5H25A—C25—H25B107.6
N2—C6—C5133.0 (4)N8—C26—N7111.1 (4)
N2—C6—C1104.8 (4)N8—C26—C25126.3 (4)
C5—C6—C1122.2 (4)N7—C26—C25122.6 (3)
N2—C7—N1110.6 (4)C28—C27—N7132.9 (4)
N2—C7—C8123.9 (3)C28—C27—C32122.5 (4)
N1—C7—C8125.4 (3)N7—C27—C32104.6 (4)
C7—C8—C9115.0 (3)C29—C28—C27117.0 (4)
C7—C8—H8A108.5C29—C28—H28121.5
C9—C8—H8A108.5C27—C28—H28121.5
C7—C8—H8B108.5C28—C29—C30121.3 (4)
C9—C8—H8B108.5C28—C29—H29119.3
H8A—C8—H8B107.5C30—C29—H29119.3
C10—C9—C8115.0 (3)C31—C30—C29122.5 (4)
C10—C9—H9A108.5C31—C30—H30118.8
C8—C9—H9A108.5C29—C30—H30118.8
C10—C9—H9B108.5C30—C31—C32116.6 (4)
C8—C9—H9B108.5C30—C31—H31121.7
H9A—C9—H9B107.5C32—C31—H31121.7
N4—C10—N3110.6 (3)N8—C32—C27109.2 (3)
N4—C10—C9127.7 (4)N8—C32—C31130.6 (4)
N3—C10—C9121.7 (3)C27—C32—C31120.1 (4)
N4—Zn1—N1—C7−28.8 (3)C12—C13—C14—C15−0.5 (6)
Cl1—Zn1—N1—C787.8 (3)C13—C14—C15—C160.2 (6)
Cl2—Zn1—N1—C7−147.0 (3)N3—C11—C16—N4−0.3 (4)
N4—Zn1—N1—C1145.0 (3)C12—C11—C16—N4177.9 (4)
Cl1—Zn1—N1—C1−98.3 (3)N3—C11—C16—C15−179.8 (3)
Cl2—Zn1—N1—C126.9 (3)C12—C11—C16—C15−1.6 (6)
N1—Zn1—N4—C1012.5 (3)C10—N4—C16—C110.4 (4)
Cl1—Zn1—N4—C10−107.1 (3)Zn1—N4—C16—C11−177.9 (2)
Cl2—Zn1—N4—C10132.2 (3)C10—N4—C16—C15179.8 (4)
N1—Zn1—N4—C16−169.8 (3)Zn1—N4—C16—C151.5 (5)
Cl1—Zn1—N4—C1670.6 (3)C14—C15—C16—C110.7 (5)
Cl2—Zn1—N4—C16−50.0 (3)C14—C15—C16—N4−178.6 (3)
N8—Zn2—N5—C233.8 (4)C23—N5—C17—C18179.8 (4)
Cl4—Zn2—N5—C23−116.4 (3)Zn2—N5—C17—C18−1.8 (6)
Cl3—Zn2—N5—C23123.3 (3)C23—N5—C17—C22−0.6 (4)
N8—Zn2—N5—C17−174.1 (3)Zn2—N5—C17—C22177.8 (2)
Cl4—Zn2—N5—C1765.7 (3)N5—C17—C18—C19177.8 (5)
Cl3—Zn2—N5—C17−54.6 (3)C22—C17—C18—C19−1.8 (7)
N5—Zn2—N8—C2619.8 (3)C17—C18—C19—C200.3 (8)
Cl4—Zn2—N8—C26140.6 (3)C18—C19—C20—C211.6 (8)
Cl3—Zn2—N8—C26−101.3 (3)C19—C20—C21—C22−1.8 (7)
N5—Zn2—N8—C32−164.5 (3)C23—N6—C22—C21178.4 (4)
Cl4—Zn2—N8—C32−43.7 (3)C23—N6—C22—C170.3 (4)
Cl3—Zn2—N8—C3274.4 (3)C20—C21—C22—N6−177.4 (4)
C7—N1—C1—C6−0.6 (4)C20—C21—C22—C170.3 (6)
Zn1—N1—C1—C6−175.3 (3)C18—C17—C22—N6179.8 (4)
C7—N1—C1—C2−178.0 (4)N5—C17—C22—N60.1 (4)
Zn1—N1—C1—C27.3 (6)C18—C17—C22—C211.5 (6)
N1—C1—C2—C3178.4 (4)N5—C17—C22—C21−178.2 (4)
C6—C1—C2—C31.2 (6)C17—N5—C23—N60.8 (4)
C1—C2—C3—C4−1.3 (7)Zn2—N5—C23—N6−177.4 (3)
C2—C3—C4—C51.0 (8)C17—N5—C23—C24−177.7 (4)
C3—C4—C5—C6−0.5 (7)Zn2—N5—C23—C244.1 (5)
C7—N2—C6—C5178.6 (5)C22—N6—C23—N5−0.7 (4)
C7—N2—C6—C1−0.5 (4)C22—N6—C23—C24177.9 (3)
C4—C5—C6—N2−178.5 (5)N5—C23—C24—C25−54.7 (5)
C4—C5—C6—C10.4 (7)N6—C23—C24—C25127.0 (4)
N1—C1—C6—N20.7 (4)C23—C24—C25—C2692.8 (4)
C2—C1—C6—N2178.4 (4)C32—N8—C26—N70.8 (4)
N1—C1—C6—C5−178.6 (4)Zn2—N8—C26—N7177.1 (2)
C2—C1—C6—C5−0.8 (6)C32—N8—C26—C25−179.5 (3)
C6—N2—C7—N10.2 (5)Zn2—N8—C26—C25−3.2 (5)
C6—N2—C7—C8−178.3 (4)C27—N7—C26—N8−0.8 (4)
C1—N1—C7—N20.2 (4)C27—N7—C26—C25179.5 (3)
Zn1—N1—C7—N2175.4 (2)C24—C25—C26—N8−56.7 (5)
C1—N1—C7—C8178.7 (4)C24—C25—C26—N7123.0 (4)
Zn1—N1—C7—C8−6.2 (5)C26—N7—C27—C28179.8 (4)
N2—C7—C8—C9−104.4 (4)C26—N7—C27—C320.5 (4)
N1—C7—C8—C977.3 (5)N7—C27—C28—C29178.7 (4)
C7—C8—C9—C10−88.8 (4)C32—C27—C28—C29−2.1 (6)
C16—N4—C10—N3−0.3 (4)C27—C28—C29—C300.4 (6)
Zn1—N4—C10—N3177.6 (2)C28—C29—C30—C311.0 (7)
C16—N4—C10—C9179.9 (4)C29—C30—C31—C32−0.7 (6)
Zn1—N4—C10—C9−2.2 (6)C26—N8—C32—C27−0.5 (4)
C11—N3—C10—N40.2 (4)Zn2—N8—C32—C27−177.0 (2)
C11—N3—C10—C9180.0 (3)C26—N8—C32—C31177.4 (4)
C8—C9—C10—N435.1 (6)Zn2—N8—C32—C310.9 (6)
C8—C9—C10—N3−144.7 (4)C28—C27—C32—N8−179.4 (4)
C10—N3—C11—C12−177.8 (4)N7—C27—C32—N80.0 (4)
C10—N3—C11—C160.1 (4)C28—C27—C32—C312.5 (6)
N3—C11—C12—C13178.9 (4)N7—C27—C32—C31−178.1 (3)
C16—C11—C12—C131.3 (6)C30—C31—C32—N8−178.7 (4)
C11—C12—C13—C14−0.3 (6)C30—C31—C32—C27−1.0 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···Cl30.862.643.316 (3)137
N3—H3···Cl4i0.862.763.291 (3)121
N6—H6···Cl1ii0.862.393.225 (3)164
N7—H7···Cl2iii0.862.523.277 (3)148

Symmetry codes: (i) −x, y−1/2, −z+2; (ii) x, y, z+1; (iii) −x+1, y+1/2, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5133).

References

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