metal-organic compounds
Bis(1-benzyl-1H-benzimidazole-κN3)dichloridozinc
aCentre Composites Nanocomposites, Moroccan Foundation for Advanced Science, Innovation and Research (MAScIR), Rabat Design Center, Rue Mohamed Al Jazouli-Madinat Al Irfane, Rabat 10100, Morocco, bLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco, and cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: em_essassi@yahoo.fr
In the title compound, [ZnCl2(C14H12N2)2], the ZnII atom exhibits a distorted tetrahedral coordination geometry involving two chloride anions and two N-atom donors from 1-benzyl-1H-benzimidazole ligands. In both ligands, the benzyl and benzimidazole rings are nearly perpendicular [dihedral angles = 81.7 (2) and 81.5 (2)°]. The two benzimidazole systems are essentially planar [maximum deviations = 0.015 (3) and 0.020 (2) Å] and form a dihedral angle of 78.09 (8)°. In the crystal, centrosymmetrically related molecules are linked by pairs of C—H⋯Cl hydrogen bonds into chains parallel to the a axis.
CCDC reference: 985748
Related literature
For background to the biochemical properties of benzimidazole derivatives, see: Mann et al. (2001); Naithani et al. (1990); Goudgaon et al. (2004). For the structures of related compounds see: Abdel-Ghani & Mansour (2011, 2012); Ahuja & Prasad (1976).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 985748
10.1107/S1600536814002840/rz5104sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814002840/rz5104Isup2.hkl
The title compound was prepared by the reaction of ZnCl2 (164 mg, 1.2 mmol) in water (10 ml) and 1-benzyl-1H-benzimidazole (500 mg, 2.4 mmol) in ethanol (10 ml). The mixture was stirred for 12 h, filtered and set aside to crystallize at ambient temperature for several days, giving colourless single crystals on slow evaporation of the solvent.
H atoms were located in a difference Fourier map and treated as riding with C—H = 0.93–0.97 Å (methylene), and with Uiso(H) = 1.2 Ueq(C). Three outliers (0 0 1, 1 0 0, 0 1 0) were omitted in the last cycles of refinement.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles. |
[ZnCl2(C14H12N2)2] | V = 1332.79 (10) Å3 |
Mr = 552.78 | Z = 2 |
Triclinic, P1 | F(000) = 568 |
Hall symbol: -p 1 | Dx = 1.377 Mg m−3 |
a = 9.9819 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.0564 (4) Å | µ = 1.15 mm−1 |
c = 13.6641 (6) Å | T = 296 K |
α = 99.539 (2)° | Block, colourless |
β = 92.087 (2)° | 0.37 × 0.32 × 0.26 mm |
γ = 99.122 (2)° |
Bruker X8 APEX diffractometer | 7403 independent reflections |
Radiation source: fine-focus sealed tube | 5928 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 29.6°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −13→13 |
Tmin = 0.682, Tmax = 0.840 | k = −13→13 |
30968 measured reflections | l = −18→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0551P)2 + 0.3641P] where P = (Fo2 + 2Fc2)/3 |
7403 reflections | (Δ/σ)max < 0.001 |
318 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
[ZnCl2(C14H12N2)2] | γ = 99.122 (2)° |
Mr = 552.78 | V = 1332.79 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.9819 (4) Å | Mo Kα radiation |
b = 10.0564 (4) Å | µ = 1.15 mm−1 |
c = 13.6641 (6) Å | T = 296 K |
α = 99.539 (2)° | 0.37 × 0.32 × 0.26 mm |
β = 92.087 (2)° |
Bruker X8 APEX diffractometer | 7403 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 5928 reflections with I > 2σ(I) |
Tmin = 0.682, Tmax = 0.840 | Rint = 0.026 |
30968 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.58 e Å−3 |
7403 reflections | Δρmin = −0.24 e Å−3 |
318 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against all reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7633 (4) | 0.8525 (3) | 0.4366 (3) | 0.1008 (11) | |
H1 | 0.7791 | 0.9301 | 0.4072 | 0.121* | |
C2 | 0.8206 (5) | 0.8556 (4) | 0.5311 (3) | 0.1210 (14) | |
H2 | 0.8754 | 0.9350 | 0.5641 | 0.145* | |
C3 | 0.7979 (4) | 0.7450 (5) | 0.5757 (2) | 0.1088 (13) | |
H3 | 0.8379 | 0.7477 | 0.6387 | 0.131* | |
C4 | 0.7162 (4) | 0.6296 (4) | 0.5281 (3) | 0.1052 (12) | |
H4 | 0.6985 | 0.5537 | 0.5593 | 0.126* | |
C5 | 0.6591 (4) | 0.6246 (3) | 0.4331 (2) | 0.0826 (8) | |
H5 | 0.6036 | 0.5451 | 0.4010 | 0.099* | |
C6 | 0.6835 (2) | 0.7356 (2) | 0.38635 (17) | 0.0602 (5) | |
C7 | 0.6298 (3) | 0.7325 (3) | 0.28114 (18) | 0.0675 (6) | |
H7A | 0.6199 | 0.8247 | 0.2733 | 0.085 (9)* | |
H7B | 0.6962 | 0.7031 | 0.2359 | 0.084 (9)* | |
C8 | 0.3754 (2) | 0.6587 (2) | 0.29074 (15) | 0.0539 (5) | |
C9 | 0.3381 (3) | 0.7496 (3) | 0.36933 (17) | 0.0692 (6) | |
H9 | 0.4018 | 0.8181 | 0.4071 | 0.083* | |
C10 | 0.2033 (4) | 0.7334 (3) | 0.3883 (2) | 0.0799 (8) | |
H10 | 0.1754 | 0.7914 | 0.4411 | 0.096* | |
C11 | 0.1069 (3) | 0.6330 (3) | 0.3312 (2) | 0.0775 (7) | |
H11 | 0.0163 | 0.6255 | 0.3465 | 0.093* | |
C12 | 0.1428 (3) | 0.5448 (3) | 0.25247 (19) | 0.0644 (6) | |
H12 | 0.0780 | 0.4784 | 0.2138 | 0.077* | |
C13 | 0.2792 (2) | 0.5583 (2) | 0.23266 (15) | 0.0510 (4) | |
C14 | 0.4755 (2) | 0.5385 (2) | 0.17551 (15) | 0.0538 (5) | |
H14 | 0.5432 | 0.5085 | 0.1369 | 0.065* | |
C15 | −0.2428 (3) | 0.2655 (3) | 0.2558 (2) | 0.0821 (8) | |
H15 | −0.1617 | 0.3181 | 0.2437 | 0.099* | |
C16 | −0.2920 (5) | 0.2837 (4) | 0.3495 (2) | 0.1078 (12) | |
H16 | −0.2421 | 0.3458 | 0.4010 | 0.129* | |
C17 | −0.4137 (4) | 0.2106 (5) | 0.3665 (2) | 0.1047 (13) | |
H17 | −0.4492 | 0.2271 | 0.4285 | 0.126* | |
C18 | −0.4834 (3) | 0.1131 (4) | 0.2925 (2) | 0.0917 (10) | |
H18 | −0.5648 | 0.0613 | 0.3049 | 0.110* | |
C19 | −0.4329 (2) | 0.0915 (3) | 0.19898 (18) | 0.0638 (6) | |
H19 | −0.4797 | 0.0243 | 0.1490 | 0.077* | |
C20 | −0.3139 (2) | 0.1694 (2) | 0.18024 (15) | 0.0487 (4) | |
C21 | −0.26224 (18) | 0.1483 (2) | 0.07709 (15) | 0.0491 (4) | |
H21A | −0.3058 | 0.0600 | 0.0407 | 0.059* | |
H21B | −0.2862 | 0.2182 | 0.0418 | 0.059* | |
C22 | −0.04380 (18) | 0.06922 (18) | 0.12376 (13) | 0.0409 (4) | |
C23 | −0.0871 (2) | −0.0469 (2) | 0.16412 (17) | 0.0570 (5) | |
H23 | −0.1788 | −0.0802 | 0.1678 | 0.068* | |
C24 | 0.0132 (3) | −0.1098 (2) | 0.1982 (2) | 0.0688 (6) | |
H24 | −0.0113 | −0.1878 | 0.2261 | 0.083* | |
C25 | 0.1510 (3) | −0.0600 (2) | 0.19231 (18) | 0.0638 (6) | |
H25 | 0.2157 | −0.1056 | 0.2166 | 0.077* | |
C26 | 0.1940 (2) | 0.0551 (2) | 0.15140 (15) | 0.0510 (4) | |
H26 | 0.2858 | 0.0878 | 0.1472 | 0.061* | |
C27 | 0.09351 (18) | 0.11926 (18) | 0.11694 (12) | 0.0393 (3) | |
C28 | −0.02314 (18) | 0.24853 (19) | 0.05074 (14) | 0.0447 (4) | |
H28 | −0.0461 | 0.3176 | 0.0191 | 0.054* | |
N1 | 0.49942 (19) | 0.6426 (2) | 0.25291 (13) | 0.0562 (4) | |
N2 | 0.34613 (17) | 0.48349 (18) | 0.16007 (13) | 0.0515 (4) | |
N3 | 0.10356 (15) | 0.23339 (16) | 0.07047 (12) | 0.0443 (3) | |
N4 | −0.11488 (15) | 0.15456 (16) | 0.08096 (12) | 0.0425 (3) | |
Zn1 | 0.26873 (2) | 0.35268 (2) | 0.034848 (16) | 0.04370 (8) | |
Cl1 | 0.18906 (5) | 0.46699 (5) | −0.07679 (4) | 0.05779 (14) | |
Cl2 | 0.43183 (5) | 0.23659 (6) | −0.01957 (4) | 0.05514 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.128 (3) | 0.0754 (18) | 0.082 (2) | −0.0178 (19) | −0.027 (2) | 0.0067 (16) |
C2 | 0.147 (4) | 0.105 (3) | 0.085 (2) | −0.009 (2) | −0.049 (2) | −0.015 (2) |
C3 | 0.131 (3) | 0.130 (3) | 0.0621 (17) | 0.044 (3) | −0.0313 (19) | −0.005 (2) |
C4 | 0.139 (3) | 0.101 (2) | 0.081 (2) | 0.032 (2) | −0.024 (2) | 0.0289 (19) |
C5 | 0.105 (2) | 0.0691 (16) | 0.0702 (16) | 0.0086 (15) | −0.0213 (15) | 0.0133 (13) |
C6 | 0.0603 (13) | 0.0638 (13) | 0.0514 (11) | 0.0031 (10) | −0.0037 (10) | 0.0035 (10) |
C7 | 0.0673 (14) | 0.0725 (15) | 0.0551 (12) | −0.0147 (12) | −0.0033 (11) | 0.0164 (11) |
C8 | 0.0656 (13) | 0.0573 (11) | 0.0423 (10) | 0.0116 (10) | −0.0011 (9) | 0.0186 (8) |
C9 | 0.0940 (19) | 0.0659 (14) | 0.0497 (12) | 0.0184 (13) | −0.0031 (12) | 0.0124 (10) |
C10 | 0.107 (2) | 0.0841 (18) | 0.0608 (14) | 0.0472 (17) | 0.0141 (15) | 0.0157 (13) |
C11 | 0.0728 (16) | 0.094 (2) | 0.0791 (17) | 0.0406 (15) | 0.0165 (14) | 0.0269 (15) |
C12 | 0.0562 (12) | 0.0737 (15) | 0.0688 (14) | 0.0189 (11) | 0.0059 (11) | 0.0198 (12) |
C13 | 0.0550 (11) | 0.0539 (11) | 0.0479 (10) | 0.0116 (9) | 0.0019 (8) | 0.0177 (8) |
C14 | 0.0516 (11) | 0.0620 (12) | 0.0454 (10) | −0.0021 (9) | 0.0040 (8) | 0.0136 (9) |
C15 | 0.090 (2) | 0.0796 (18) | 0.0657 (15) | −0.0004 (15) | 0.0121 (14) | −0.0051 (13) |
C16 | 0.128 (3) | 0.124 (3) | 0.0638 (18) | 0.033 (3) | 0.0048 (19) | −0.0162 (18) |
C17 | 0.099 (2) | 0.178 (4) | 0.0517 (15) | 0.064 (3) | 0.0180 (16) | 0.0198 (19) |
C18 | 0.0571 (15) | 0.161 (3) | 0.0696 (17) | 0.0273 (18) | 0.0195 (13) | 0.045 (2) |
C19 | 0.0406 (10) | 0.0944 (17) | 0.0597 (12) | 0.0133 (11) | 0.0059 (9) | 0.0199 (12) |
C20 | 0.0455 (10) | 0.0543 (11) | 0.0502 (10) | 0.0158 (8) | 0.0057 (8) | 0.0124 (8) |
C21 | 0.0338 (8) | 0.0610 (11) | 0.0525 (10) | 0.0051 (8) | 0.0037 (7) | 0.0129 (9) |
C22 | 0.0399 (8) | 0.0422 (9) | 0.0400 (8) | 0.0031 (7) | −0.0006 (7) | 0.0099 (7) |
C23 | 0.0510 (11) | 0.0547 (11) | 0.0668 (13) | −0.0035 (9) | 0.0029 (9) | 0.0267 (10) |
C24 | 0.0727 (15) | 0.0575 (13) | 0.0822 (16) | 0.0032 (11) | −0.0030 (12) | 0.0387 (12) |
C25 | 0.0673 (14) | 0.0640 (13) | 0.0676 (14) | 0.0189 (11) | −0.0075 (11) | 0.0279 (11) |
C26 | 0.0440 (10) | 0.0595 (11) | 0.0519 (10) | 0.0106 (8) | −0.0034 (8) | 0.0160 (9) |
C27 | 0.0400 (8) | 0.0402 (8) | 0.0375 (8) | 0.0043 (7) | −0.0002 (6) | 0.0092 (7) |
C28 | 0.0408 (9) | 0.0429 (9) | 0.0539 (10) | 0.0070 (7) | 0.0038 (8) | 0.0182 (8) |
N1 | 0.0570 (10) | 0.0648 (11) | 0.0434 (8) | −0.0043 (8) | −0.0011 (7) | 0.0144 (8) |
N2 | 0.0464 (9) | 0.0572 (10) | 0.0502 (9) | 0.0023 (7) | 0.0031 (7) | 0.0129 (7) |
N3 | 0.0377 (7) | 0.0442 (8) | 0.0539 (9) | 0.0042 (6) | 0.0031 (6) | 0.0189 (7) |
N4 | 0.0359 (7) | 0.0451 (8) | 0.0479 (8) | 0.0051 (6) | 0.0031 (6) | 0.0140 (6) |
Zn1 | 0.03618 (11) | 0.04504 (13) | 0.05179 (14) | 0.00320 (8) | 0.00320 (8) | 0.01722 (9) |
Cl1 | 0.0506 (3) | 0.0594 (3) | 0.0722 (3) | 0.0134 (2) | 0.0037 (2) | 0.0330 (3) |
Cl2 | 0.0428 (2) | 0.0630 (3) | 0.0643 (3) | 0.0156 (2) | 0.0044 (2) | 0.0178 (2) |
C1—C6 | 1.373 (4) | C15—H15 | 0.9300 |
C1—C2 | 1.386 (5) | C16—C17 | 1.365 (6) |
C1—H1 | 0.9300 | C16—H16 | 0.9300 |
C2—C3 | 1.347 (6) | C17—C18 | 1.368 (5) |
C2—H2 | 0.9300 | C17—H17 | 0.9300 |
C3—C4 | 1.359 (5) | C18—C19 | 1.387 (4) |
C3—H3 | 0.9300 | C18—H18 | 0.9300 |
C4—C5 | 1.388 (4) | C19—C20 | 1.372 (3) |
C4—H4 | 0.9300 | C19—H19 | 0.9300 |
C5—C6 | 1.370 (4) | C20—C21 | 1.512 (3) |
C5—H5 | 0.9300 | C21—N4 | 1.461 (2) |
C6—C7 | 1.509 (3) | C21—H21A | 0.9700 |
C7—N1 | 1.461 (3) | C21—H21B | 0.9700 |
C7—H7A | 0.9700 | C22—N4 | 1.382 (2) |
C7—H7B | 0.9700 | C22—C23 | 1.387 (3) |
C8—N1 | 1.381 (3) | C22—C27 | 1.395 (2) |
C8—C9 | 1.393 (3) | C23—C24 | 1.372 (3) |
C8—C13 | 1.394 (3) | C23—H23 | 0.9300 |
C9—C10 | 1.369 (4) | C24—C25 | 1.398 (4) |
C9—H9 | 0.9300 | C24—H24 | 0.9300 |
C10—C11 | 1.389 (4) | C25—C26 | 1.382 (3) |
C10—H10 | 0.9300 | C25—H25 | 0.9300 |
C11—C12 | 1.373 (4) | C26—C27 | 1.384 (3) |
C11—H11 | 0.9300 | C26—H26 | 0.9300 |
C12—C13 | 1.387 (3) | C27—N3 | 1.393 (2) |
C12—H12 | 0.9300 | C28—N3 | 1.321 (2) |
C13—N2 | 1.398 (3) | C28—N4 | 1.336 (2) |
C14—N2 | 1.316 (3) | C28—H28 | 0.9300 |
C14—N1 | 1.344 (3) | N2—Zn1 | 2.0225 (17) |
C14—H14 | 0.9300 | N3—Zn1 | 2.0048 (15) |
C15—C20 | 1.380 (3) | Zn1—Cl2 | 2.2292 (5) |
C15—C16 | 1.382 (4) | Zn1—Cl1 | 2.2503 (5) |
C6—C1—C2 | 120.4 (3) | C17—C18—C19 | 120.1 (3) |
C6—C1—H1 | 119.8 | C17—C18—H18 | 120.0 |
C2—C1—H1 | 119.8 | C19—C18—H18 | 120.0 |
C3—C2—C1 | 120.9 (3) | C20—C19—C18 | 120.0 (3) |
C3—C2—H2 | 119.6 | C20—C19—H19 | 120.0 |
C1—C2—H2 | 119.6 | C18—C19—H19 | 120.0 |
C2—C3—C4 | 119.6 (3) | C19—C20—C15 | 119.6 (2) |
C2—C3—H3 | 120.2 | C19—C20—C21 | 119.6 (2) |
C4—C3—H3 | 120.2 | C15—C20—C21 | 120.8 (2) |
C3—C4—C5 | 120.2 (3) | N4—C21—C20 | 111.42 (16) |
C3—C4—H4 | 119.9 | N4—C21—H21A | 109.3 |
C5—C4—H4 | 119.9 | C20—C21—H21A | 109.3 |
C6—C5—C4 | 120.7 (3) | N4—C21—H21B | 109.3 |
C6—C5—H5 | 119.6 | C20—C21—H21B | 109.3 |
C4—C5—H5 | 119.6 | H21A—C21—H21B | 108.0 |
C5—C6—C1 | 118.3 (3) | N4—C22—C23 | 131.75 (17) |
C5—C6—C7 | 122.6 (2) | N4—C22—C27 | 105.86 (15) |
C1—C6—C7 | 119.2 (2) | C23—C22—C27 | 122.35 (17) |
N1—C7—C6 | 114.19 (19) | C24—C23—C22 | 116.2 (2) |
N1—C7—H7A | 108.7 | C24—C23—H23 | 121.9 |
C6—C7—H7A | 108.7 | C22—C23—H23 | 121.9 |
N1—C7—H7B | 108.7 | C23—C24—C25 | 121.9 (2) |
C6—C7—H7B | 108.7 | C23—C24—H24 | 119.0 |
H7A—C7—H7B | 107.6 | C25—C24—H24 | 119.0 |
N1—C8—C9 | 132.6 (2) | C26—C25—C24 | 121.8 (2) |
N1—C8—C13 | 106.03 (19) | C26—C25—H25 | 119.1 |
C9—C8—C13 | 121.4 (2) | C24—C25—H25 | 119.1 |
C10—C9—C8 | 116.9 (3) | C25—C26—C27 | 116.63 (19) |
C10—C9—H9 | 121.6 | C25—C26—H26 | 121.7 |
C8—C9—H9 | 121.6 | C27—C26—H26 | 121.7 |
C9—C10—C11 | 122.0 (3) | C26—C27—N3 | 130.31 (17) |
C9—C10—H10 | 119.0 | C26—C27—C22 | 121.08 (17) |
C11—C10—H10 | 119.0 | N3—C27—C22 | 108.59 (15) |
C12—C11—C10 | 121.3 (3) | N3—C28—N4 | 113.13 (16) |
C12—C11—H11 | 119.4 | N3—C28—H28 | 123.4 |
C10—C11—H11 | 119.4 | N4—C28—H28 | 123.4 |
C11—C12—C13 | 117.7 (3) | C14—N1—C8 | 107.04 (18) |
C11—C12—H12 | 121.2 | C14—N1—C7 | 125.4 (2) |
C13—C12—H12 | 121.2 | C8—N1—C7 | 127.1 (2) |
C12—C13—C8 | 120.7 (2) | C14—N2—C13 | 105.48 (18) |
C12—C13—N2 | 130.8 (2) | C14—N2—Zn1 | 123.26 (15) |
C8—C13—N2 | 108.46 (19) | C13—N2—Zn1 | 129.57 (14) |
N2—C14—N1 | 113.0 (2) | C28—N3—C27 | 105.30 (14) |
N2—C14—H14 | 123.5 | C28—N3—Zn1 | 124.79 (12) |
N1—C14—H14 | 123.5 | C27—N3—Zn1 | 129.89 (12) |
C20—C15—C16 | 120.0 (3) | C28—N4—C22 | 107.12 (15) |
C20—C15—H15 | 120.0 | C28—N4—C21 | 126.89 (16) |
C16—C15—H15 | 120.0 | C22—N4—C21 | 125.84 (15) |
C17—C16—C15 | 120.2 (3) | N3—Zn1—N2 | 107.29 (7) |
C17—C16—H16 | 119.9 | N3—Zn1—Cl2 | 113.31 (5) |
C15—C16—H16 | 119.9 | N2—Zn1—Cl2 | 107.21 (5) |
C16—C17—C18 | 120.1 (3) | N3—Zn1—Cl1 | 104.56 (5) |
C16—C17—H17 | 119.9 | N2—Zn1—Cl1 | 110.42 (5) |
C18—C17—H17 | 119.9 | Cl2—Zn1—Cl1 | 113.88 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···Cl1i | 0.93 | 2.81 | 3.660 (2) | 153 |
C28—H28···Cl1ii | 0.93 | 2.80 | 3.502 (2) | 133 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···Cl1i | 0.93 | 2.81 | 3.660 (2) | 153 |
C28—H28···Cl1ii | 0.93 | 2.80 | 3.502 (2) | 133 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z. |
Acknowledgements
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Benzimidazole derivatives are important pharmacophores in drug discovery, possessing pharmacological properties including antitumor (Mann et al., 2001), anti-Parkinson (Naithani et al., 1990) and antimicrobial (Goudgaon et al., 2004) activities. A considerable number of metal benzimidazole complexes including Cr, Mn, Fe, Co, Ni, Zn, Pd, Pt, Au, and Re has been reported (Abdel-Ghani & Mansour, 2011, 2012). Metal complexes of biologically important ligands were sometimes more effective than the free ligands (Ahuja & Prasad, 1976).
The crystal structure of the title compound, show that the ZnII ion adopts a distorted tetrahedral coordination arising from two N-atom donors from organic ligands and a two Cl- anions (Fig. 1). The fused five- and six-membered rings are nearly coplanar with dihedral angles between them of 1.0 (2)° and 1.6 (2)° respectively. The dihedral angle between the two benzimidazole systems is of 78.09 (8)°. Each benzyl ring (C1–C6 and C15–C20) is virtually perpendicular to the benzimidazole system belonging to the same molecule (N1/N2/C8–C14 and N3/N4/C22–C28) as indicated by the dihedral angles between them of 81.7 (2)° and 81.5 (2)°, respectively. In the crystal, centrosymmetrically-related molecules are linked by C—H···Cl hydrogen bonds (Table 1) into chains running parallel to the a axis.