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

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catena-Poly[[[di­chloridozinc(II)]-μ-1,4-bis­­(1H-benzimidazol-2-yl-κN3)butane] 1,4-bis­­(1H-benzimidazol-2-yl)butane solvate]

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

(Received 7 December 2009; accepted 7 December 2009; online 12 December 2009)

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[Albada, G. A. van, Lakin, M. T., Veldman, N., Spek, A. J. & Reedijk, J. (1995). Inorg. Chem. 34, 4910-4917.]). For other metal(II) dichloride adducts of this N-heterocycle, see: Chen et al. (2005[Chen, C.-L., Zhang, J.-A., Li, X.-P., Chen, Z.-N., Kang, B.-S. & Su, C.-S. (2005). Inorg. Chim. Acta, 358, 4527-4533.]); Wang et al. (2006[Wang, Y., Xu, H.-B., Su, Z.-M., Shao, K.-Z., Zhao, Y.-H., Cui, H.-P., Lan, Y.-Q. & Hao, X.-R. (2006). Inorg. Chem. Commun. 9, 1207-1211.]).

[Scheme 1]

Experimental

Crystal data
  • [ZnCl2(C18H18N4)]·C18H18N4

  • Mr = 717.00

  • Monoclinic, P 21 /c

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.687, Tmax = 0.840

  • 17738 measured reflections

  • 7549 independent reflections

  • 3855 reflections with I > 2σ(I)

  • Rint = 0.052

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 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

Table 1
Selected bond lengths (Å)

Zn1—N1 2.033 (3)
Zn1—N3i 2.024 (3)
Zn1—Cl1 2.248 (1)
Zn1—Cl2 2.247 (1)
Symmetry code: (i) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯N5 0.88 (1) 1.92 (1) 2.787 (5) 169 (4)
N4—H4⋯N8ii 0.88 (1) 1.90 (1) 2.773 (5) 175 (4)
N6—H6⋯Cl1iii 0.88 (1) 2.37 (2) 3.224 (4) 167 (5)
N7—H7⋯Cl2iv 0.88 (1) 2.35 (1) 3.230 (4) 178 (4)
Symmetry codes: (ii) x-1, y, z; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. 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 Aldaba et al. (1995). For other metal(II) dichloride adducts of this N-heterocycle, see: Chen et al. (2005); Wang et al. (2006).

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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. 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.
catena-Poly[[[dichloridozinc(II)]-µ-1,4-bis(1H-benzimidazol-2- yl-κN3)butane] 1,4-bis(1H-benzimidazol-2-yl)butane solvate] top
Crystal data top
[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 top
Bruker APEXII area-detector
diffractometer
7549 independent reflections
Radiation source: fine-focus sealed tube3855 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ϕ and ω scansθmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.687, Tmax = 0.840k = 3018
17738 measured reflectionsl = 1921
Refinement top
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 = 1.02 w = 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 = 0.70 e Å3
Crystal data top
[ZnCl2(C18H18N4)]·C18H18N4V = 3468.9 (4) Å3
Mr = 717.00Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.5321 (5) ŵ = 0.90 mm1
b = 24.119 (2) ÅT = 173 K
c = 16.880 (1) Å0.45 × 0.30 × 0.20 mm
β = 92.999 (1)°
Data collection top
Bruker APEXII area-detector
diffractometer
7549 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3855 reflections with I > 2σ(I)
Tmin = 0.687, Tmax = 0.840Rint = 0.052
17738 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06232 restraints
wR(F2) = 0.192H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 1.10 e Å3
7549 reflectionsΔρmin = 0.70 e Å3
448 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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*
N30.1295 (4)0.49956 (13)0.8346 (2)0.0243 (8)
N40.0076 (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*
H11B0.01310.51720.69710.040*
C120.0323 (5)0.53918 (16)0.8124 (2)0.0243 (10)
C130.1716 (5)0.51441 (17)0.9110 (3)0.0272 (10)
C140.2741 (5)0.4896 (2)0.9620 (3)0.0396 (12)
H140.32660.45590.94860.047*
C150.2956 (6)0.5164 (2)1.0328 (3)0.0509 (15)
H150.36520.50051.06860.061*
C160.2204 (7)0.5652 (2)1.0538 (3)0.0521 (15)
H160.23950.58221.10320.063*
C170.1178 (6)0.5895 (2)1.0040 (3)0.0445 (13)
H170.06460.62291.01820.053*
C180.0950 (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*
C210.0121 (7)0.6897 (3)0.5254 (4)0.0686 (19)
H210.09020.67110.49320.082*
C220.0268 (6)0.7454 (3)0.5375 (4)0.0639 (18)
H220.11580.76400.51410.077*
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) top
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, º) top
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—C754.6 (3)C25—N5—C19—C20180.0 (5)
Cl2—Zn1—N1—C7169.3 (3)N5—C19—C20—C21178.7 (5)
Cl1—Zn1—N1—C764.8 (3)C24—C19—C20—C210.2 (8)
N3i—Zn1—N1—C1110.9 (3)C19—C20—C21—C221.4 (9)
Cl2—Zn1—N1—C13.9 (4)C20—C21—C22—C231.2 (10)
Cl1—Zn1—N1—C1129.7 (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—C61.0 (4)C22—C23—C24—N6179.4 (6)
Zn1—N1—C1—C6168.3 (3)C22—C23—C24—C191.5 (8)
C6—C1—C2—C30.6 (6)N5—C19—C24—N61.2 (5)
N1—C1—C2—C3178.4 (4)C20—C19—C24—N6179.7 (5)
C1—C2—C3—C40.4 (7)N5—C19—C24—C23179.6 (5)
C2—C3—C4—C50.0 (8)C20—C19—C24—C231.3 (8)
C3—C4—C5—C60.1 (7)C19—N5—C25—N60.4 (6)
C4—C5—C6—N2178.1 (5)C19—N5—C25—C26178.0 (5)
C4—C5—C6—C10.1 (7)C24—N6—C25—N50.4 (6)
C7—N2—C6—C5177.7 (5)C24—N6—C25—C26178.8 (5)
C7—N2—C6—C10.5 (5)N5—C25—C26—C27'24.1 (18)
C2—C1—C6—C50.5 (6)N6—C25—C26—C27'154.1 (15)
N1—C1—C6—C5178.7 (4)N5—C25—C26—C27135.4 (7)
C2—C1—C6—N2178.9 (4)N6—C25—C26—C2746.4 (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—C8177.5 (4)C26—C27—C28—C2984.5 (6)
Zn1—N1—C7—C89.1 (6)C25—C26—C27'—C28'169.7 (9)
C6—N2—C7—N11.2 (5)C26—C27'—C28'—C2987.3 (14)
C6—N2—C7—C8177.7 (4)C25—C26—C27"—C28"147.5 (10)
N1—C7—C8—C9142.7 (4)C26—C27"—C28"—C2988.2 (15)
N2—C7—C8—C938.5 (6)C27"—C28"—C29—C2835.5 (15)
C7—C8—C9—C1061.9 (5)C27"—C28"—C29—C30169.5 (9)
C8—C9—C10—C11175.5 (4)C27—C28—C29—C30164.5 (4)
C9—C10—C11—C1273.1 (5)C27'—C28'—C29—C28100.9 (10)
C13—N3—C12—N41.0 (4)C27'—C28'—C29—C30149.4 (8)
Zn1ii—N3—C12—N4166.7 (3)C36—N8—C30—N70.2 (6)
C13—N3—C12—C11179.0 (4)C36—N8—C30—C29178.4 (5)
Zn1ii—N3—C12—C1115.2 (6)C31—N7—C30—N80.2 (6)
C18—N4—C12—N31.0 (5)C31—N7—C30—C29178.4 (5)
C18—N4—C12—C11179.2 (4)C28"—C29—C30—N820 (2)
C10—C11—C12—N3101.0 (5)C28—C29—C30—N8132.5 (6)
C10—C11—C12—N476.9 (5)C28'—C29—C30—N876.2 (10)
C12—N3—C13—C180.6 (4)C28"—C29—C30—N7158.9 (17)
Zn1ii—N3—C13—C18165.2 (3)C28—C29—C30—N749.0 (8)
C12—N3—C13—C14177.4 (4)C28'—C29—C30—N7105.3 (9)
Zn1ii—N3—C13—C1412.8 (6)C30—N7—C31—C32179.6 (5)
C18—C13—C14—C150.8 (6)C30—N7—C31—C360.2 (5)
N3—C13—C14—C15177.0 (4)N7—C31—C32—C33179.1 (5)
C13—C14—C15—C160.3 (7)C36—C31—C32—C331.1 (8)
C14—C15—C16—C170.4 (8)C31—C32—C33—C341.0 (9)
C15—C16—C17—C180.6 (7)C32—C33—C34—C350.7 (9)
C12—N4—C18—C17176.8 (5)C33—C34—C35—C360.5 (9)
C12—N4—C18—C130.6 (5)C34—C35—C36—N8179.7 (5)
C16—C17—C18—N4176.9 (5)C34—C35—C36—C310.7 (8)
C16—C17—C18—C130.1 (7)C30—N8—C36—C35179.1 (5)
C14—C13—C18—N4178.3 (4)C30—N8—C36—C310.1 (5)
N3—C13—C18—N40.0 (4)N7—C31—C36—C35179.1 (5)
C14—C13—C18—C170.6 (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—N8179.8 (5)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
Hydrogen-bond geometry (Å, º) top
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) x1, y, z; (iii) x+1, y+1/2, z+3/2; (iv) x+2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[ZnCl2(C18H18N4)]·C18H18N4
Mr717.00
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)8.5321 (5), 24.119 (2), 16.880 (1)
β (°) 92.999 (1)
V3)3468.9 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.90
Crystal size (mm)0.45 × 0.30 × 0.20
Data collection
DiffractometerBruker APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.687, 0.840
No. of measured, independent and
observed [I > 2σ(I)] reflections
17738, 7549, 3855
Rint0.052
(sin θ/λ)max1)0.640
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.192, 1.02
No. of reflections7549
No. of parameters448
No. of restraints32
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.10, 0.70

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top
Zn1—N12.033 (3)Zn1—Cl12.248 (1)
Zn1—N3i2.024 (3)Zn1—Cl22.247 (1)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
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) x1, y, z; (iii) x+1, y+1/2, z+3/2; (iv) x+2, y+1/2, z+3/2.
 

Acknowledgements

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

References

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First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChen, C.-L., Zhang, J.-A., Li, X.-P., Chen, Z.-N., Kang, B.-S. & Su, C.-S. (2005). Inorg. Chim. Acta, 358, 4527–4533.  Web of Science CSD CrossRef CAS 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 citationWang, Y., Xu, H.-B., Su, Z.-M., Shao, K.-Z., Zhao, Y.-H., Cui, H.-P., Lan, Y.-Q. & Hao, X.-R. (2006). Inorg. Chem. Commun. 9, 1207–1211.  Web of Science CSD CrossRef CAS Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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