metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

[1,2-Bis(1H-benzimidazol-2-yl-κN3)ethane]di­chloridozinc(II)

aSchool of Chemistry & Chemical Engineering, Guangxi Normal University, 541004 Guilin 541004, People's Republic of China, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 8 December 2009; accepted 8 December 2009; online 12 December 2009)

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[Albada, G. A. van, Lakin, M. T., Veldman, N., Spek, A. J. & Reedijk, J. (1995). Inorg. Chem. 34, 4910-4917.]). For the zinc dichloride adduct of a similar N-heterocycle, see: Zhou et al. (2010[Zhou, Y.-L., Zeng, M.-H. & Ng, S. W. (2010). Acta Cryst. E66, m58.]).

[Scheme 1]

Experimental

Crystal data
  • [ZnCl2(C16H14N4)]

  • Mr = 398.58

  • Monoclinic, P 21

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.479, Tmax = 0.614

  • 8555 measured reflections

  • 5820 independent reflections

  • 4956 reflections with I > 2σ(I)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2049 Friedel pairs

  • Flack parameter: 0.1 (1)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯Cl3 0.86 2.64 3.316 (3) 137
N3—H3⋯Cl4i 0.86 2.76 3.291 (3) 121
N6—H6⋯Cl1ii 0.86 2.39 3.225 (3) 164
N7—H7⋯Cl2iii 0.86 2.52 3.277 (3) 148
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+2]; (ii) x, y, z+1; (iii) [-x+1, y+{\script{1\over 2}}, -z+2].

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

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

Experimental top

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 top

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)].

Computing details top

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

Figures top
[Figure 1] 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.
[1,2-Bis(1H-benzimidazol-2-yl-κN3)ethane]dichloridozinc(II) top
Crystal data top
[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 top
Bruker SMART
diffractometer
5820 independent reflections
Radiation source: fine-focus sealed tube4956 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ϕ and ω scansθmax = 27.1°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.479, Tmax = 0.614k = 1713
8555 measured reflectionsl = 1815
Refinement top
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) = 0.077 w = 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 methodsAbsolute structure parameter: 0.1 (1)
Crystal data top
[ZnCl2(C16H14N4)]V = 1662.7 (2) Å3
Mr = 398.58Z = 4
Monoclinic, P21Mo Kα radiation
a = 8.0868 (4) ŵ = 1.80 mm1
b = 13.8605 (8) ÅT = 293 K
c = 14.8504 (8) Å0.48 × 0.34 × 0.30 mm
β = 92.664 (1)°
Data collection top
Bruker SMART
diffractometer
5820 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4956 reflections with I > 2σ(I)
Tmin = 0.479, Tmax = 0.614Rint = 0.018
8555 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.077Δρmax = 0.30 e Å3
S = 0.97Δρmin = 0.30 e Å3
5820 reflectionsAbsolute structure: Flack (1983), 2049 Friedel pairs
415 parametersAbsolute structure parameter: 0.1 (1)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
Cl10.01667 (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)
Cl40.01188 (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) top
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, º) top
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—C728.8 (3)C12—C13—C14—C150.5 (6)
Cl1—Zn1—N1—C787.8 (3)C13—C14—C15—C160.2 (6)
Cl2—Zn1—N1—C7147.0 (3)N3—C11—C16—N40.3 (4)
N4—Zn1—N1—C1145.0 (3)C12—C11—C16—N4177.9 (4)
Cl1—Zn1—N1—C198.3 (3)N3—C11—C16—C15179.8 (3)
Cl2—Zn1—N1—C126.9 (3)C12—C11—C16—C151.6 (6)
N1—Zn1—N4—C1012.5 (3)C10—N4—C16—C110.4 (4)
Cl1—Zn1—N4—C10107.1 (3)Zn1—N4—C16—C11177.9 (2)
Cl2—Zn1—N4—C10132.2 (3)C10—N4—C16—C15179.8 (4)
N1—Zn1—N4—C16169.8 (3)Zn1—N4—C16—C151.5 (5)
Cl1—Zn1—N4—C1670.6 (3)C14—C15—C16—C110.7 (5)
Cl2—Zn1—N4—C1650.0 (3)C14—C15—C16—N4178.6 (3)
N8—Zn2—N5—C233.8 (4)C23—N5—C17—C18179.8 (4)
Cl4—Zn2—N5—C23116.4 (3)Zn2—N5—C17—C181.8 (6)
Cl3—Zn2—N5—C23123.3 (3)C23—N5—C17—C220.6 (4)
N8—Zn2—N5—C17174.1 (3)Zn2—N5—C17—C22177.8 (2)
Cl4—Zn2—N5—C1765.7 (3)N5—C17—C18—C19177.8 (5)
Cl3—Zn2—N5—C1754.6 (3)C22—C17—C18—C191.8 (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—C26101.3 (3)C19—C20—C21—C221.8 (7)
N5—Zn2—N8—C32164.5 (3)C23—N6—C22—C21178.4 (4)
Cl4—Zn2—N8—C3243.7 (3)C23—N6—C22—C170.3 (4)
Cl3—Zn2—N8—C3274.4 (3)C20—C21—C22—N6177.4 (4)
C7—N1—C1—C60.6 (4)C20—C21—C22—C170.3 (6)
Zn1—N1—C1—C6175.3 (3)C18—C17—C22—N6179.8 (4)
C7—N1—C1—C2178.0 (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—C21178.2 (4)
C6—C1—C2—C31.2 (6)C17—N5—C23—N60.8 (4)
C1—C2—C3—C41.3 (7)Zn2—N5—C23—N6177.4 (3)
C2—C3—C4—C51.0 (8)C17—N5—C23—C24177.7 (4)
C3—C4—C5—C60.5 (7)Zn2—N5—C23—C244.1 (5)
C7—N2—C6—C5178.6 (5)C22—N6—C23—N50.7 (4)
C7—N2—C6—C10.5 (4)C22—N6—C23—C24177.9 (3)
C4—C5—C6—N2178.5 (5)N5—C23—C24—C2554.7 (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—C5178.6 (4)Zn2—N8—C26—N7177.1 (2)
C2—C1—C6—C50.8 (6)C32—N8—C26—C25179.5 (3)
C6—N2—C7—N10.2 (5)Zn2—N8—C26—C253.2 (5)
C6—N2—C7—C8178.3 (4)C27—N7—C26—N80.8 (4)
C1—N1—C7—N20.2 (4)C27—N7—C26—C25179.5 (3)
Zn1—N1—C7—N2175.4 (2)C24—C25—C26—N856.7 (5)
C1—N1—C7—C8178.7 (4)C24—C25—C26—N7123.0 (4)
Zn1—N1—C7—C86.2 (5)C26—N7—C27—C28179.8 (4)
N2—C7—C8—C9104.4 (4)C26—N7—C27—C320.5 (4)
N1—C7—C8—C977.3 (5)N7—C27—C28—C29178.7 (4)
C7—C8—C9—C1088.8 (4)C32—C27—C28—C292.1 (6)
C16—N4—C10—N30.3 (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—C320.7 (6)
Zn1—N4—C10—C92.2 (6)C26—N8—C32—C270.5 (4)
C11—N3—C10—N40.2 (4)Zn2—N8—C32—C27177.0 (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—N3144.7 (4)C28—C27—C32—N8179.4 (4)
C10—N3—C11—C12177.8 (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—C31178.1 (3)
C16—C11—C12—C131.3 (6)C30—C31—C32—N8178.7 (4)
C11—C12—C13—C140.3 (6)C30—C31—C32—C271.0 (6)
Hydrogen-bond geometry (Å, º) top
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, y1/2, z+2; (ii) x, y, z+1; (iii) x+1, y+1/2, z+2.

Experimental details

Crystal data
Chemical formula[ZnCl2(C16H14N4)]
Mr398.58
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)8.0868 (4), 13.8605 (8), 14.8504 (8)
β (°) 92.664 (1)
V3)1662.7 (2)
Z4
Radiation typeMo Kα
µ (mm1)1.80
Crystal size (mm)0.48 × 0.34 × 0.30
Data collection
DiffractometerBruker SMART
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.479, 0.614
No. of measured, independent and
observed [I > 2σ(I)] reflections
8555, 5820, 4956
Rint0.018
(sin θ/λ)max1)0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.077, 0.97
No. of reflections5820
No. of parameters415
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.30
Absolute structureFlack (1983), 2049 Friedel pairs
Absolute structure parameter0.1 (1)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
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, y1/2, z+2; (ii) x, y, z+1; (iii) x+1, y+1/2, z+2.
 

Acknowledgements

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

References

First citationAlbada, G. A. van, Lakin, M. T., Veldman, N., Spek, A. J. & Reedijk, J. (1995). Inorg. Chem. 34, 4910–4917.  Google Scholar
First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar
First citationZhou, Y.-L., Zeng, M.-H. & Ng, S. W. (2010). Acta Cryst. E66, m58.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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