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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): m58.
Published online 2009 December 12. doi:  10.1107/S1600536809052635
PMCID: PMC2980004

catena-Poly[[[dichloridozinc(II)]-μ-1,4-bis­(1H-benzimidazol-2-yl-κN 3)butane] 1,4-bis­(1H-benzimidazol-2-yl)butane solvate]

Abstract

In the crystal structure of the title coordination polymer/co-crystal, {[ZnCl2(C18H18N4)]·C18H18N4}n, the tetrahedrally coordinated ZnII ions are linked by the N-heterocycle into a linear chain. Another N-heterocycle present is not coordinated to the metal atom but inter­acts with the chain through N—H(...)N and N—H(...)Cl hydrogen bonds. The butyl chain of the uncoordinated ligand is disordered over three positions in a 0.511 (4):0.289 (5):0.200 (5) ratio.

Related literature

For the synthesis of the ligand, see: van Aldaba et al. (1995 [triangle]). For other metal(II) dichloride adducts of this N-heterocycle, see: Chen et al. (2005 [triangle]); Wang et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-00m58-scheme1.jpg

Experimental

Crystal data

  • [ZnCl2(C18H18N4)]·C18H18N4
  • M r = 717.00
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00m58-efi1.jpg
  • a = 8.5321 (5) Å
  • b = 24.119 (2) Å
  • c = 16.880 (1) Å
  • β = 92.999 (1)°
  • V = 3468.9 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.90 mm−1
  • T = 173 K
  • 0.45 × 0.30 × 0.20 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.687, T max = 0.840
  • 17738 measured reflections
  • 7549 independent reflections
  • 3855 reflections with I > 2σ(I)
  • R int = 0.052

Refinement

  • R[F 2 > 2σ(F 2)] = 0.062
  • wR(F 2) = 0.192
  • S = 1.02
  • 7549 reflections
  • 448 parameters
  • 32 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.10 e Å−3
  • Δρmin = −0.70 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052635/ci2985sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052635/ci2985Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

1,4-Bis(2-benzimidazolyl)butane 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 (0.27 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 d. The cool solution yielded red block single crystals in ca 30% yield.

Refinement

Carbon-bound hydrogen atoms were generated geometrically and were constrained to ride on their parent atoms [C–H = 0.95–0.99 Å and Uiso(H) = 1.2Ueq(C)]. The nitrogen-bound ones were located in a difference Fourier map, and were refined with a N-H distance restraint of 0.88 (1) Å; their temperature factors were similarly tied.

The butyl chain of the uncoordinated ligand is disordered over three positions with occupancies of 0.511 (4), 0.289 (5) and 0.200 (5). The 1,2-related distances were restrained to 1.50 (1) Å and the 1,3-related ones to 2.35 (1) Å. The final difference Fourier map had a peak in the vicinity of the disordered atoms.

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of a portion of the polymeric structure of ZnCl2(C18H18N4).C18H18N4 at the 50% probability level. H atoms are drawn as sphere of arbitrary radius. Only the major disorder component of the butyl chain is shown. ...

Crystal data

[ZnCl2(C18H18N4)]·C18H18N4F(000) = 1488
Mr = 717.00Dx = 1.373 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3392 reflections
a = 8.5321 (5) Åθ = 2.4–25.2°
b = 24.119 (2) ŵ = 0.90 mm1
c = 16.880 (1) ÅT = 173 K
β = 92.999 (1)°Block, red
V = 3468.9 (4) Å30.45 × 0.30 × 0.20 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer7549 independent reflections
Radiation source: fine-focus sealed tube3855 reflections with I > 2σ(I)
graphiteRint = 0.052
[var phi] and ω scansθmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.687, Tmax = 0.840k = −30→18
17738 measured reflectionsl = −19→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0962P)2] where P = (Fo2 + 2Fc2)/3
7549 reflections(Δ/σ)max = 0.001
448 parametersΔρmax = 1.10 e Å3
32 restraintsΔρmin = −0.69 e Å3

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

xyzUiso*/UeqOcc. (<1)
Zn10.76884 (6)0.443756 (19)0.75855 (3)0.03034 (19)
Cl10.58239 (17)0.39129 (5)0.81075 (9)0.0579 (4)
Cl20.95928 (16)0.39314 (5)0.70655 (9)0.0518 (4)
N10.6603 (4)0.49713 (13)0.6803 (2)0.0239 (8)
N20.5260 (4)0.57190 (14)0.6425 (2)0.0293 (9)
H20.468 (4)0.6019 (11)0.637 (3)0.035*
N3−0.1295 (4)0.49956 (13)0.8346 (2)0.0243 (8)
N4−0.0076 (4)0.57767 (15)0.8695 (2)0.0297 (9)
H40.042 (5)0.6091 (10)0.864 (3)0.036*
N50.3642 (5)0.67223 (16)0.6438 (2)0.0434 (11)
N60.3359 (5)0.76206 (16)0.6609 (3)0.0419 (11)
H60.360 (6)0.7956 (9)0.677 (3)0.050*
N71.1593 (5)0.76918 (15)0.8373 (2)0.0405 (10)
H71.125 (5)0.8026 (9)0.825 (3)0.049*
N81.1417 (5)0.67940 (16)0.8606 (2)0.0388 (10)
C10.6918 (5)0.50889 (16)0.6017 (2)0.0247 (10)
C20.7893 (5)0.48250 (19)0.5501 (3)0.0360 (11)
H2a0.84720.45020.56550.043*
C30.7981 (6)0.5056 (2)0.4750 (3)0.0437 (13)
H30.86410.48870.43830.052*
C40.7138 (6)0.5523 (2)0.4520 (3)0.0430 (13)
H4A0.72300.56670.40010.052*
C50.6168 (6)0.57815 (19)0.5029 (3)0.0381 (12)
H50.55850.61020.48720.046*
C60.6070 (5)0.55583 (17)0.5777 (3)0.0284 (10)
C70.5620 (5)0.53660 (16)0.7022 (3)0.0256 (10)
C80.4998 (5)0.54272 (18)0.7826 (3)0.0315 (11)
H8A0.56650.56960.81320.038*
H8B0.50930.50660.81020.038*
C90.3315 (5)0.56169 (18)0.7834 (3)0.0339 (11)
H9A0.30290.56650.83900.041*
H9B0.32140.59820.75670.041*
C100.2204 (5)0.5219 (2)0.7431 (3)0.0371 (11)
H10A0.22590.48640.77240.044*
H10B0.25560.51470.68910.044*
C110.0455 (5)0.54116 (19)0.7360 (3)0.0330 (11)
H11A0.04100.57960.71540.040*
H11B−0.01310.51720.69710.040*
C12−0.0323 (5)0.53918 (16)0.8124 (2)0.0243 (10)
C13−0.1716 (5)0.51441 (17)0.9110 (3)0.0272 (10)
C14−0.2741 (5)0.4896 (2)0.9620 (3)0.0396 (12)
H14−0.32660.45590.94860.047*
C15−0.2956 (6)0.5164 (2)1.0328 (3)0.0509 (15)
H15−0.36520.50051.06860.061*
C16−0.2204 (7)0.5652 (2)1.0538 (3)0.0521 (15)
H16−0.23950.58221.10320.063*
C17−0.1178 (6)0.5895 (2)1.0040 (3)0.0445 (13)
H17−0.06460.62291.01820.053*
C18−0.0950 (5)0.56348 (17)0.9328 (3)0.0287 (10)
C190.2264 (5)0.68930 (18)0.6044 (3)0.0313 (11)
C200.1127 (7)0.6592 (2)0.5586 (3)0.0571 (16)
H200.12100.62030.55090.069*
C21−0.0121 (7)0.6897 (3)0.5254 (4)0.0686 (19)
H21−0.09020.67110.49320.082*
C22−0.0268 (6)0.7454 (3)0.5375 (4)0.0639 (18)
H22−0.11580.76400.51410.077*
C230.0817 (6)0.7754 (2)0.5818 (3)0.0511 (15)
H230.07050.81420.59010.061*
C240.2081 (5)0.74616 (18)0.6138 (3)0.0315 (11)
C250.4246 (6)0.7171 (2)0.6767 (3)0.0455 (14)
C260.5745 (7)0.7182 (3)0.7284 (4)0.093 (3)
H26A0.54450.72040.78420.112*0.511 (4)
H26B0.62740.68210.72210.112*0.511 (4)
H26C0.65090.73280.69150.112*0.289 (5)
H26D0.55520.74950.76460.112*0.289 (5)
H26E0.58440.75440.75610.112*0.200 (5)
H26F0.57170.68870.76910.112*0.200 (5)
C270.6908 (8)0.7616 (3)0.7171 (5)0.086 (4)0.511 (4)
H27A0.63850.79810.71250.103*0.511 (4)
H27B0.74530.75460.66770.103*0.511 (4)
C280.8063 (8)0.7613 (3)0.7867 (5)0.065 (3)0.511 (4)
H28A0.85540.79830.79330.078*0.511 (4)
H28B0.75250.75230.83570.078*0.511 (4)
C27'0.6698 (13)0.6826 (6)0.7778 (11)0.086 (4)0.289 (5)
H27C0.72090.65480.74470.103*0.289 (5)
H27D0.60330.66260.81480.103*0.289 (5)
C28'0.7909 (11)0.7148 (8)0.8236 (7)0.065 (3)0.289 (5)
H28C0.82170.69550.87380.078*0.289 (5)
H28D0.75060.75200.83630.078*0.289 (5)
C27"0.7118 (12)0.7096 (11)0.6788 (7)0.086 (4)0.200 (5)
H27E0.68090.68760.63100.103*0.200 (5)
H27F0.75400.74570.66180.103*0.200 (5)
C28"0.8301 (14)0.6796 (6)0.7288 (14)0.065 (3)0.200 (5)
H28E0.77750.65480.76590.078*0.200 (5)
H28F0.89590.65660.69510.078*0.200 (5)
C290.9271 (6)0.7194 (3)0.7729 (4)0.0680 (19)
H29A0.95520.72230.71690.082*0.511 (4)
H29B0.87990.68230.77980.082*0.511 (4)
H29C0.91670.75320.73970.082*0.289 (5)
H29D0.93030.68690.73720.082*0.289 (5)
H29E0.85050.73690.80710.082*0.200 (5)
H29F0.94650.74750.73190.082*0.200 (5)
C301.0769 (6)0.7222 (2)0.8247 (3)0.0421 (13)
C311.2901 (5)0.75633 (18)0.8853 (3)0.0320 (11)
C321.4133 (6)0.7881 (2)0.9160 (3)0.0442 (13)
H321.42100.82660.90480.053*
C331.5239 (6)0.7611 (2)0.9633 (3)0.0548 (16)
H331.60990.78160.98630.066*
C341.5145 (6)0.7049 (2)0.9788 (3)0.0538 (16)
H341.59450.68781.01150.065*
C351.3913 (6)0.6729 (2)0.9477 (3)0.0463 (14)
H351.38500.63440.95890.056*
C361.2775 (5)0.69929 (18)0.8997 (3)0.0328 (11)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.0306 (3)0.0192 (3)0.0406 (4)0.0004 (2)−0.0038 (2)−0.0001 (2)
Cl10.0530 (9)0.0321 (7)0.0887 (11)−0.0170 (6)0.0056 (8)0.0139 (7)
Cl20.0455 (8)0.0338 (7)0.0754 (10)0.0136 (6)−0.0030 (7)−0.0160 (6)
N10.0207 (18)0.0230 (18)0.028 (2)0.0031 (14)−0.0005 (16)−0.0037 (15)
N20.027 (2)0.029 (2)0.032 (2)0.0114 (16)0.0011 (18)0.0021 (17)
N30.0224 (19)0.0229 (18)0.027 (2)−0.0016 (15)−0.0021 (16)0.0008 (15)
N40.028 (2)0.027 (2)0.034 (2)−0.0068 (16)0.0033 (18)−0.0030 (17)
N50.054 (3)0.040 (2)0.036 (2)0.029 (2)0.000 (2)0.0014 (19)
N60.032 (2)0.037 (2)0.056 (3)0.0006 (19)−0.007 (2)−0.015 (2)
N70.036 (2)0.033 (2)0.051 (3)−0.0021 (19)−0.010 (2)0.007 (2)
N80.040 (2)0.038 (2)0.038 (2)−0.0135 (19)0.001 (2)−0.0025 (18)
C10.019 (2)0.029 (2)0.026 (2)−0.0010 (17)−0.0019 (19)−0.0047 (18)
C20.030 (3)0.044 (3)0.035 (3)0.008 (2)0.001 (2)−0.010 (2)
C30.037 (3)0.063 (3)0.032 (3)0.008 (3)0.006 (2)−0.012 (3)
C40.050 (3)0.053 (3)0.027 (3)−0.007 (3)0.006 (2)−0.003 (2)
C50.044 (3)0.036 (3)0.034 (3)0.001 (2)−0.004 (2)0.004 (2)
C60.027 (2)0.027 (2)0.031 (3)−0.0042 (19)0.002 (2)−0.002 (2)
C70.021 (2)0.025 (2)0.031 (3)0.0023 (18)−0.001 (2)−0.0044 (18)
C80.027 (2)0.033 (3)0.035 (3)0.0068 (19)0.008 (2)−0.0011 (19)
C90.028 (2)0.040 (3)0.035 (3)0.003 (2)0.009 (2)0.000 (2)
C100.046 (3)0.038 (3)0.029 (3)−0.006 (2)0.016 (2)−0.010 (2)
C110.029 (3)0.042 (3)0.029 (3)−0.002 (2)0.003 (2)−0.002 (2)
C120.020 (2)0.024 (2)0.028 (2)0.0036 (17)−0.0012 (19)0.0013 (18)
C130.020 (2)0.034 (2)0.027 (2)0.0016 (19)−0.001 (2)0.0052 (19)
C140.031 (3)0.053 (3)0.035 (3)0.001 (2)0.002 (2)0.017 (2)
C150.038 (3)0.083 (4)0.032 (3)0.008 (3)0.010 (3)0.019 (3)
C160.048 (3)0.076 (4)0.033 (3)0.015 (3)0.004 (3)−0.002 (3)
C170.050 (3)0.048 (3)0.035 (3)0.005 (3)0.002 (3)−0.008 (2)
C180.022 (2)0.037 (3)0.027 (3)0.0029 (19)−0.001 (2)0.002 (2)
C190.032 (3)0.032 (2)0.030 (3)0.005 (2)0.001 (2)0.004 (2)
C200.068 (4)0.042 (3)0.061 (4)−0.017 (3)0.003 (3)−0.012 (3)
C210.041 (4)0.095 (5)0.068 (5)−0.023 (4)−0.013 (3)−0.011 (4)
C220.033 (3)0.092 (5)0.066 (4)0.002 (3)−0.013 (3)0.014 (4)
C230.033 (3)0.052 (3)0.068 (4)0.010 (2)−0.006 (3)0.017 (3)
C240.022 (2)0.029 (2)0.043 (3)0.0016 (18)−0.006 (2)0.003 (2)
C250.030 (3)0.069 (4)0.037 (3)0.022 (3)−0.007 (2)−0.008 (3)
C260.047 (4)0.162 (7)0.070 (5)0.035 (5)−0.011 (4)−0.052 (5)
C270.072 (6)0.078 (6)0.106 (7)−0.007 (6)−0.017 (6)0.014 (6)
C280.050 (5)0.061 (5)0.082 (6)−0.006 (5)−0.014 (5)−0.012 (5)
C27'0.072 (6)0.078 (6)0.106 (7)−0.007 (6)−0.017 (6)0.014 (6)
C28'0.050 (5)0.061 (5)0.082 (6)−0.006 (5)−0.014 (5)−0.012 (5)
C27"0.072 (6)0.078 (6)0.106 (7)−0.007 (6)−0.017 (6)0.014 (6)
C28"0.050 (5)0.061 (5)0.082 (6)−0.006 (5)−0.014 (5)−0.012 (5)
C290.045 (4)0.097 (5)0.061 (4)−0.019 (3)−0.011 (3)0.030 (3)
C300.032 (3)0.053 (3)0.040 (3)−0.012 (2)−0.007 (2)0.007 (2)
C310.021 (2)0.034 (3)0.040 (3)−0.0011 (19)−0.004 (2)−0.006 (2)
C320.039 (3)0.034 (3)0.059 (4)−0.006 (2)−0.005 (3)−0.006 (2)
C330.034 (3)0.056 (4)0.073 (4)−0.006 (3)−0.012 (3)−0.019 (3)
C340.037 (3)0.065 (4)0.058 (4)0.013 (3)−0.015 (3)−0.005 (3)
C350.049 (3)0.034 (3)0.056 (4)0.010 (2)−0.002 (3)0.005 (2)
C360.026 (3)0.033 (3)0.039 (3)−0.003 (2)0.000 (2)−0.002 (2)

Geometric parameters (Å, °)

Zn1—N12.033 (3)C17—H170.95
Zn1—N3i2.024 (3)C19—C241.390 (6)
Zn1—Cl12.248 (1)C19—C201.409 (7)
Zn1—Cl22.247 (1)C20—C211.387 (8)
N1—C71.334 (5)C20—H200.95
N1—C11.395 (5)C21—C221.365 (8)
N2—C71.342 (5)C21—H210.95
N2—C61.381 (6)C22—C231.368 (8)
N2—H20.876 (10)C22—H220.95
N3—C121.332 (5)C23—C241.375 (6)
N3—C131.402 (5)C23—H230.95
N3—Zn1ii2.024 (3)C25—C261.511 (7)
N4—C121.347 (5)C26—C27'1.423 (9)
N4—C181.378 (6)C26—C271.460 (7)
N4—H40.878 (10)C26—C27"1.490 (10)
N5—C251.310 (6)C26—H26A0.99
N5—C191.383 (6)C26—H26B0.99
N6—C251.341 (6)C26—H26C0.99
N6—C241.370 (5)C26—H26D0.99
N6—H60.875 (10)C26—H26E0.99
N7—C301.345 (6)C26—H26F0.99
N7—C311.379 (6)C27—C281.4936
N7—H70.879 (10)C27—H27A0.99
N8—C301.305 (6)C27—H27B0.99
N8—C361.388 (6)C28—C291.471 (7)
C1—C21.390 (6)C28—H28A0.99
C1—C61.392 (5)C28—H28B0.99
C2—C31.391 (7)C27'—C28'1.477 (9)
C2—H2a0.95C27'—H27C0.99
C3—C41.381 (7)C27'—H27D0.99
C3—H30.95C28'—C291.483 (9)
C4—C51.375 (7)C28'—H28C0.99
C4—H4A0.95C28'—H28D0.99
C5—C61.378 (6)C27"—C28"1.471 (10)
C5—H50.95C27"—H27E0.99
C7—C81.490 (6)C27"—H27F0.99
C8—C91.508 (6)C28"—C291.448 (10)
C8—H8A0.99C28"—H28E0.99
C8—H8B0.99C28"—H28F0.99
C9—C101.488 (6)C29—C301.512 (7)
C9—H9A0.99C29—H29A0.99
C9—H9B0.99C29—H29B0.99
C10—C111.561 (6)C29—H29C0.99
C10—H10A0.99C29—H29D0.99
C10—H10B0.99C29—H29E0.99
C11—C121.482 (6)C29—H29F0.99
C11—H11A0.99C31—C321.380 (6)
C11—H11B0.99C31—C361.402 (6)
C13—C181.392 (6)C32—C331.369 (7)
C13—C141.394 (6)C32—H320.95
C14—C151.378 (7)C33—C341.384 (7)
C14—H140.95C33—H330.95
C15—C161.379 (7)C34—C351.384 (7)
C15—H150.95C34—H340.95
C16—C171.376 (7)C35—C361.386 (6)
C16—H160.95C35—H350.95
C17—C181.379 (6)
N3i—Zn1—N199.03 (13)C23—C22—H22118.7
N3i—Zn1—Cl2108.33 (10)C22—C23—C24115.9 (5)
N1—Zn1—Cl2113.83 (10)C22—C23—H23122.0
N3i—Zn1—Cl1114.47 (11)C24—C23—H23122.0
N1—Zn1—Cl1107.68 (11)N6—C24—C23131.9 (4)
Cl2—Zn1—Cl1112.84 (6)N6—C24—C19104.6 (4)
C7—N1—C1105.9 (3)C23—C24—C19123.5 (4)
C7—N1—Zn1122.9 (3)N5—C25—N6112.3 (4)
C1—N1—Zn1130.0 (3)N5—C25—C26124.2 (5)
C7—N2—C6108.2 (3)N6—C25—C26123.5 (5)
C7—N2—H2135 (3)C27—C26—C25119.8 (6)
C6—N2—H2117 (3)C27"—C26—C25109.8 (6)
C12—N3—C13105.6 (3)C27—C26—H26A107.4
C12—N3—Zn1ii123.4 (3)C25—C26—H26A107.4
C13—N3—Zn1ii129.1 (3)C27—C26—H26B107.4
C12—N4—C18108.2 (4)C25—C26—H26B107.4
C12—N4—H4125 (3)H26A—C26—H26B106.9
C18—N4—H4126 (3)C27'—C26—H26C102.0
C25—N5—C19105.3 (4)C25—C26—H26C102.0
C25—N6—C24108.2 (4)C27'—C26—H26D102.0
C25—N6—H6124 (3)C25—C26—H26D102.0
C24—N6—H6127 (3)H26C—C26—H26D104.8
C30—N7—C31107.7 (4)C27'—C26—H26E102.9
C30—N7—H7125 (3)C27"—C26—H26E109.7
C31—N7—H7127 (3)C25—C26—H26E109.7
C30—N8—C36105.7 (4)C27"—C26—H26F109.7
C2—C1—C6120.5 (4)C25—C26—H26F109.7
C2—C1—N1130.8 (4)H26E—C26—H26F108.2
C6—C1—N1108.7 (4)C26—C27—C28108.6 (4)
C1—C2—C3116.8 (4)C26—C27—H27A110.0
C1—C2—H2a121.6C28—C27—H27A110.0
C3—C2—H2a121.6C26—C27—H27B110.0
C4—C3—C2122.1 (5)C28—C27—H27B110.0
C4—C3—H3119.0H27A—C27—H27B108.4
C2—C3—H3119.0C29—C28—C27108.5 (4)
C5—C4—C3121.1 (5)C29—C28—H28A110.0
C5—C4—H4A119.5C27—C28—H28A110.0
C3—C4—H4A119.5C29—C28—H28B110.0
C4—C5—C6117.6 (4)C27—C28—H28B110.0
C4—C5—H5121.2H28A—C28—H28B108.4
C6—C5—H5121.2C26—C27'—C28'110.6 (9)
C5—C6—N2132.3 (4)C26—C27'—H27C109.5
C5—C6—C1122.0 (4)C28'—C27'—H27C109.5
N2—C6—C1105.7 (4)C26—C27'—H27D109.5
N1—C7—N2111.5 (4)C28'—C27'—H27D109.5
N1—C7—C8125.6 (4)H27C—C27'—H27D108.1
N2—C7—C8122.8 (4)C27'—C28'—C29106.6 (9)
C7—C8—C9115.0 (4)C27'—C28'—H28C110.4
C7—C8—H8A108.5C29—C28'—H28C110.4
C9—C8—H8A108.5C27'—C28'—H28D110.4
C7—C8—H8B108.5C29—C28'—H28D110.4
C9—C8—H8B108.5H28C—C28'—H28D108.6
H8A—C8—H8B107.5C28"—C27"—C26106.4 (9)
C10—C9—C8112.6 (4)C28"—C27"—H27E110.5
C10—C9—H9A109.1C26—C27"—H27E110.5
C8—C9—H9A109.1C28"—C27"—H27F110.5
C10—C9—H9B109.1C26—C27"—H27F110.5
C8—C9—H9B109.1H27E—C27"—H27F108.6
H9A—C9—H9B107.8C29—C28"—C27"109.0 (10)
C9—C10—C11115.3 (4)C29—C28"—H28E109.9
C9—C10—H10A108.5C27"—C28"—H28E109.9
C11—C10—H10A108.5C29—C28"—H28F109.9
C9—C10—H10B108.5C27"—C28"—H28F109.9
C11—C10—H10B108.5H28E—C28"—H28F108.3
H10A—C10—H10B107.5C28—C29—C30117.1 (5)
C12—C11—C10113.2 (4)C28'—C29—C30109.5 (6)
C12—C11—H11A108.9C28—C29—H29A108.0
C10—C11—H11A108.9C30—C29—H29A108.0
C12—C11—H11B108.9C28—C29—H29B108.0
C10—C11—H11B108.9C30—C29—H29B108.0
H11A—C11—H11B107.8H29A—C29—H29B107.3
N3—C12—N4111.7 (4)C28"—C29—H29C102.8
N3—C12—C11125.6 (4)C28'—C29—H29C109.8
N4—C12—C11122.7 (4)C30—C29—H29C109.8
C18—C13—C14120.1 (4)C28'—C29—H29D109.8
C18—C13—N3108.7 (4)C30—C29—H29D109.8
C14—C13—N3131.1 (4)H29C—C29—H29D108.2
C15—C14—C13116.8 (5)C28"—C29—H29E101.9
C15—C14—H14121.6C30—C29—H29E101.9
C13—C14—H14121.6C28"—C29—H29F101.9
C14—C15—C16122.8 (5)C30—C29—H29F101.9
C14—C15—H15118.6H29E—C29—H29F104.7
C16—C15—H15118.6N8—C30—N7112.8 (4)
C17—C16—C15120.5 (5)N8—C30—C29123.9 (5)
C17—C16—H16119.7N7—C30—C29123.3 (5)
C15—C16—H16119.7N7—C31—C32132.3 (4)
C16—C17—C18117.6 (5)N7—C31—C36104.8 (4)
C16—C17—H17121.2C32—C31—C36122.9 (4)
C18—C17—H17121.2C33—C32—C31116.3 (5)
N4—C18—C17132.1 (4)C33—C32—H32121.8
N4—C18—C13105.8 (4)C31—C32—H32121.8
C17—C18—C13122.1 (4)C32—C33—C34122.0 (5)
N5—C19—C24109.7 (4)C32—C33—H33119.0
N5—C19—C20130.8 (5)C34—C33—H33119.0
C24—C19—C20119.5 (4)C33—C34—C35121.7 (5)
C21—C20—C19116.1 (5)C33—C34—H34119.2
C21—C20—H20121.9C35—C34—H34119.2
C19—C20—H20121.9C34—C35—C36117.4 (5)
C22—C21—C20122.4 (5)C34—C35—H35121.3
C22—C21—H21118.8C36—C35—H35121.3
C20—C21—H21118.8C35—C36—N8131.4 (4)
C21—C22—C23122.6 (5)C35—C36—C31119.6 (4)
C21—C22—H22118.7N8—C36—C31109.1 (4)
N3i—Zn1—N1—C7−54.6 (3)C25—N5—C19—C20180.0 (5)
Cl2—Zn1—N1—C7−169.3 (3)N5—C19—C20—C21−178.7 (5)
Cl1—Zn1—N1—C764.8 (3)C24—C19—C20—C210.2 (8)
N3i—Zn1—N1—C1110.9 (3)C19—C20—C21—C22−1.4 (9)
Cl2—Zn1—N1—C1−3.9 (4)C20—C21—C22—C231.2 (10)
Cl1—Zn1—N1—C1−129.7 (3)C21—C22—C23—C240.2 (9)
C7—N1—C1—C2178.1 (4)C25—N6—C24—C23179.2 (6)
Zn1—N1—C1—C210.8 (6)C25—N6—C24—C191.0 (5)
C7—N1—C1—C6−1.0 (4)C22—C23—C24—N6−179.4 (6)
Zn1—N1—C1—C6−168.3 (3)C22—C23—C24—C19−1.5 (8)
C6—C1—C2—C30.6 (6)N5—C19—C24—N6−1.2 (5)
N1—C1—C2—C3−178.4 (4)C20—C19—C24—N6179.7 (5)
C1—C2—C3—C4−0.4 (7)N5—C19—C24—C23−179.6 (5)
C2—C3—C4—C50.0 (8)C20—C19—C24—C231.3 (8)
C3—C4—C5—C60.1 (7)C19—N5—C25—N6−0.4 (6)
C4—C5—C6—N2178.1 (5)C19—N5—C25—C26178.0 (5)
C4—C5—C6—C10.1 (7)C24—N6—C25—N5−0.4 (6)
C7—N2—C6—C5−177.7 (5)C24—N6—C25—C26−178.8 (5)
C7—N2—C6—C10.5 (5)N5—C25—C26—C27'−24.1 (18)
C2—C1—C6—C5−0.5 (6)N6—C25—C26—C27'154.1 (15)
N1—C1—C6—C5178.7 (4)N5—C25—C26—C27135.4 (7)
C2—C1—C6—N2−178.9 (4)N6—C25—C26—C27−46.4 (9)
N1—C1—C6—N20.3 (4)N5—C25—C26—C27"71.9 (14)
C1—N1—C7—N21.4 (5)N6—C25—C26—C27"−109.8 (13)
Zn1—N1—C7—N2169.8 (3)C25—C26—C27—C28166.7 (4)
C1—N1—C7—C8−177.5 (4)C26—C27—C28—C2984.5 (6)
Zn1—N1—C7—C8−9.1 (6)C25—C26—C27'—C28'−169.7 (9)
C6—N2—C7—N1−1.2 (5)C26—C27'—C28'—C29−87.3 (14)
C6—N2—C7—C8177.7 (4)C25—C26—C27"—C28"−147.5 (10)
N1—C7—C8—C9−142.7 (4)C26—C27"—C28"—C29−88.2 (15)
N2—C7—C8—C938.5 (6)C27"—C28"—C29—C2835.5 (15)
C7—C8—C9—C1061.9 (5)C27"—C28"—C29—C30−169.5 (9)
C8—C9—C10—C11−175.5 (4)C27—C28—C29—C30164.5 (4)
C9—C10—C11—C12−73.1 (5)C27'—C28'—C29—C28100.9 (10)
C13—N3—C12—N41.0 (4)C27'—C28'—C29—C30−149.4 (8)
Zn1ii—N3—C12—N4166.7 (3)C36—N8—C30—N7−0.2 (6)
C13—N3—C12—C11179.0 (4)C36—N8—C30—C29178.4 (5)
Zn1ii—N3—C12—C11−15.2 (6)C31—N7—C30—N80.2 (6)
C18—N4—C12—N3−1.0 (5)C31—N7—C30—C29−178.4 (5)
C18—N4—C12—C11−179.2 (4)C28"—C29—C30—N8−20 (2)
C10—C11—C12—N3−101.0 (5)C28—C29—C30—N8132.5 (6)
C10—C11—C12—N476.9 (5)C28'—C29—C30—N876.2 (10)
C12—N3—C13—C18−0.6 (4)C28"—C29—C30—N7158.9 (17)
Zn1ii—N3—C13—C18−165.2 (3)C28—C29—C30—N7−49.0 (8)
C12—N3—C13—C14177.4 (4)C28'—C29—C30—N7−105.3 (9)
Zn1ii—N3—C13—C1412.8 (6)C30—N7—C31—C32179.6 (5)
C18—C13—C14—C150.8 (6)C30—N7—C31—C36−0.2 (5)
N3—C13—C14—C15−177.0 (4)N7—C31—C32—C33179.1 (5)
C13—C14—C15—C16−0.3 (7)C36—C31—C32—C33−1.1 (8)
C14—C15—C16—C17−0.4 (8)C31—C32—C33—C341.0 (9)
C15—C16—C17—C180.6 (7)C32—C33—C34—C35−0.7 (9)
C12—N4—C18—C17−176.8 (5)C33—C34—C35—C360.5 (9)
C12—N4—C18—C130.6 (5)C34—C35—C36—N8−179.7 (5)
C16—C17—C18—N4176.9 (5)C34—C35—C36—C31−0.7 (8)
C16—C17—C18—C13−0.1 (7)C30—N8—C36—C35179.1 (5)
C14—C13—C18—N4−178.3 (4)C30—N8—C36—C310.1 (5)
N3—C13—C18—N40.0 (4)N7—C31—C36—C35−179.1 (5)
C14—C13—C18—C17−0.6 (6)C32—C31—C36—C351.0 (8)
N3—C13—C18—C17177.7 (4)N7—C31—C36—N80.1 (5)
C25—N5—C19—C241.0 (6)C32—C31—C36—N8−179.8 (5)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···N50.88 (1)1.92 (1)2.787 (5)169 (4)
N4—H4···N8ii0.88 (1)1.90 (1)2.773 (5)175 (4)
N6—H6···Cl1iii0.88 (1)2.37 (2)3.224 (4)167 (5)
N7—H7···Cl2iv0.88 (1)2.35 (1)3.230 (4)178 (4)

Symmetry codes: (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+3/2; (iv) −x+2, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2985).

References

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