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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809052635/ci2985sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536809052635/ci2985Isup2.hkl
Contains datablock I

CCDC reference: 766676

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in main residue
  • R factor = 0.062
  • wR factor = 0.192
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop 1
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C26 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 7 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 11 PLAT731_ALERT_1_C Bond Calc 0.88(3), Rep 0.876(10) ...... 3.00 su-Ra N2 -H2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.88(3), Rep 0.878(10) ...... 3.00 su-Ra N4 -H4 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.87(3), Rep 0.875(10) ...... 3.00 su-Ra N6 -H6 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.88(3), Rep 0.879(10) ...... 3.00 su-Ra N7 -H7 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.88(3), Rep 0.880(10) ...... 3.00 su-Ra N2 -H2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.88(3), Rep 0.880(10) ...... 3.00 su-Ra N4 -H4 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.87(3), Rep 0.880(10) ...... 3.00 su-Ra N6 -H6 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.88(3), Rep 0.880(10) ...... 3.00 su-Ra N7 -H7 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.92(3), Rep 1.920(10) ...... 3.00 su-Ra H2 -N5 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.90(3), Rep 1.900(10) ...... 3.00 su-Ra H4 -N8 1.555 1.455 PLAT736_ALERT_1_C H...A Calc 2.35(3), Rep 2.350(10) ...... 3.00 su-Ra H7 -CL2 1.555 2.756 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 32
Alert level G PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 2.00 Perc. PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 32
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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.
 

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