Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100014876/ln1109sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100014876/ln1109Isup2.hkl |
CCDC reference: 158241
Solid 2-benzyl-2-benzimidazole was dissolved in EtOH/H2O. Zinc dichloride was then added at 343–353 K with stirring, refluxing for 4–5 h and then cooling. The red solution obtained was filtered and left for evaporation. After one day, the red solids were separated out and were recrystallized from EtOH/H2O. Single crystals suitable for X-ray analysis were obtained by slow evaporation at room temperature from the EtOH solvent.
After checking their presence in the difference map, the positions of all H atoms were calculated geometrically and allowed to ride on their attached atoms (N—H = 0.00 Å and C—H = 0.00–0.00 Å). The highest peak and deepest hole are located 0.91 and 0.82 Å, respectively, from the Zn atom. Examination of the structure with PLATON (Spek, 1990) showed that there were solvent accessible voids of 34 Å3 in the crystal lattice, but there was no evidence of diffuse solvent in those holes.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).
Fig. 1. The structure of title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme. |
[ZnCl2(C14H12N2)2] | F(000) = 1136 |
Mr = 552.78 | Dx = 1.438 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.8623 (2) Å | Cell parameters from 8192 reflections |
b = 16.3674 (1) Å | θ = 1.9–28.3° |
c = 14.1767 (2) Å | µ = 1.20 mm−1 |
β = 111.943 (1)° | T = 293 K |
V = 2553.08 (6) Å3 | Slab, red |
Z = 4 | 0.28 × 0.24 × 0.20 mm |
Siemens SMART CCD area-detector diffractometer | 6226 independent reflections |
Radiation source: fine-focus sealed tube | 3898 reflections with I > 2σ(I)' |
Graphite monochromator | Rint = 0.073 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 1.9° |
ω scans | h = −7→15 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −21→21 |
Tmin = 0.731, Tmax = 0.796 | l = −18→18 |
17665 measured reflections |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0592P)2] where P = (Fo2 + 2Fc2)/3 |
6226 reflections | (Δ/σ)max < 0.001 |
316 parameters | Δρmax = 0.74 e Å−3 |
0 restraints | Δρmin = −1.51 e Å−3 |
[ZnCl2(C14H12N2)2] | V = 2553.08 (6) Å3 |
Mr = 552.78 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.8623 (2) Å | µ = 1.20 mm−1 |
b = 16.3674 (1) Å | T = 293 K |
c = 14.1767 (2) Å | 0.28 × 0.24 × 0.20 mm |
β = 111.943 (1)° |
Siemens SMART CCD area-detector diffractometer | 6226 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 3898 reflections with I > 2σ(I)' |
Tmin = 0.731, Tmax = 0.796 | Rint = 0.073 |
17665 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 0.93 | Δρmax = 0.74 e Å−3 |
6226 reflections | Δρmin = −1.51 e Å−3 |
316 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible. |
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 | ||
Zn1 | 0.17445 (3) | 0.22953 (2) | 0.46297 (2) | 0.03183 (12) | |
Cl1 | 0.10770 (7) | 0.15171 (5) | 0.56294 (6) | 0.0449 (2) | |
Cl2 | 0.24012 (7) | 0.14669 (5) | 0.36634 (6) | 0.0447 (2) | |
N1 | 0.3046 (2) | 0.30088 (14) | 0.56451 (17) | 0.0327 (5) | |
N2 | 0.4786 (2) | 0.34242 (15) | 0.68028 (17) | 0.0376 (6) | |
H2A | 0.5555 | 0.3494 | 0.7112 | 0.045* | |
N3 | 0.0493 (2) | 0.30382 (14) | 0.36063 (16) | 0.0307 (5) | |
N4 | −0.1210 (2) | 0.35521 (15) | 0.24906 (18) | 0.0392 (6) | |
H4A | −0.1972 | 0.3657 | 0.2191 | 0.047* | |
C1 | 0.2795 (3) | 0.34761 (17) | 0.6377 (2) | 0.0335 (6) | |
C2 | 0.1691 (3) | 0.36735 (19) | 0.6455 (2) | 0.0450 (8) | |
H2B | 0.0953 | 0.3501 | 0.5975 | 0.054* | |
C3 | 0.1756 (3) | 0.4145 (2) | 0.7298 (3) | 0.0524 (9) | |
H3A | 0.1039 | 0.4292 | 0.7376 | 0.063* | |
C4 | 0.2858 (3) | 0.4402 (2) | 0.8022 (3) | 0.0511 (9) | |
H4B | 0.2857 | 0.4716 | 0.8568 | 0.061* | |
C5 | 0.3954 (3) | 0.42005 (19) | 0.7948 (2) | 0.0449 (8) | |
H5A | 0.4692 | 0.4369 | 0.8433 | 0.054* | |
C6 | 0.3897 (3) | 0.37346 (17) | 0.7114 (2) | 0.0352 (7) | |
C7 | 0.4253 (3) | 0.29962 (18) | 0.5939 (2) | 0.0348 (7) | |
C8 | 0.4942 (3) | 0.25770 (19) | 0.5405 (2) | 0.0404 (7) | |
H8A | 0.4556 | 0.2055 | 0.5159 | 0.049* | |
H8B | 0.5754 | 0.2466 | 0.5891 | 0.049* | |
C9 | 0.5048 (3) | 0.30437 (19) | 0.4510 (2) | 0.0349 (6) | |
C10 | 0.5147 (3) | 0.2618 (2) | 0.3712 (2) | 0.0432 (7) | |
H10A | 0.5118 | 0.2050 | 0.3716 | 0.052* | |
C11 | 0.5289 (3) | 0.3016 (2) | 0.2899 (2) | 0.0514 (9) | |
H11A | 0.5363 | 0.2716 | 0.2368 | 0.062* | |
C12 | 0.5320 (4) | 0.3845 (2) | 0.2882 (3) | 0.0602 (10) | |
H12A | 0.5414 | 0.4116 | 0.2340 | 0.072* | |
C13 | 0.5211 (4) | 0.4281 (2) | 0.3672 (3) | 0.0726 (13) | |
H13A | 0.5230 | 0.4849 | 0.3661 | 0.087* | |
C14 | 0.5072 (4) | 0.3878 (2) | 0.4487 (3) | 0.0564 (10) | |
H14A | 0.4996 | 0.4178 | 0.5017 | 0.068* | |
C15 | 0.0777 (3) | 0.34993 (16) | 0.28891 (19) | 0.0322 (6) | |
C16 | 0.1892 (3) | 0.36436 (19) | 0.2800 (2) | 0.0423 (7) | |
H16A | 0.2612 | 0.3420 | 0.3253 | 0.051* | |
C17 | 0.1868 (3) | 0.4140 (2) | 0.2000 (3) | 0.0515 (9) | |
H17A | 0.2593 | 0.4249 | 0.1914 | 0.062* | |
C18 | 0.0803 (3) | 0.4479 (2) | 0.1324 (2) | 0.0515 (9) | |
H18A | 0.0839 | 0.4817 | 0.0808 | 0.062* | |
C19 | −0.0311 (3) | 0.4331 (2) | 0.1391 (2) | 0.0481 (8) | |
H19A | −0.1027 | 0.4554 | 0.0932 | 0.058* | |
C20 | −0.0301 (3) | 0.38274 (17) | 0.2191 (2) | 0.0355 (7) | |
C21 | −0.0705 (3) | 0.30873 (18) | 0.3338 (2) | 0.0335 (6) | |
C22 | −0.1438 (3) | 0.27260 (19) | 0.3884 (2) | 0.0392 (7) | |
H22A | −0.1074 | 0.2210 | 0.4180 | 0.047* | |
H22B | −0.2247 | 0.2611 | 0.3394 | 0.047* | |
C23 | −0.1545 (3) | 0.32648 (19) | 0.4719 (2) | 0.0375 (7) | |
C24 | −0.1701 (3) | 0.2907 (2) | 0.5537 (2) | 0.0487 (8) | |
H24A | −0.1726 | 0.2341 | 0.5576 | 0.058* | |
C25 | −0.1823 (3) | 0.3379 (3) | 0.6309 (3) | 0.0624 (11) | |
H25A | −0.1921 | 0.3127 | 0.6861 | 0.075* | |
C26 | −0.1800 (4) | 0.4212 (3) | 0.6260 (3) | 0.0717 (12) | |
H26A | −0.1896 | 0.4529 | 0.6769 | 0.086* | |
C27 | −0.1635 (4) | 0.4574 (3) | 0.5455 (3) | 0.0737 (13) | |
H27A | −0.1610 | 0.5141 | 0.5422 | 0.088* | |
C28 | −0.1502 (4) | 0.4108 (2) | 0.4681 (3) | 0.0562 (10) | |
H28A | −0.1385 | 0.4364 | 0.4139 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0340 (2) | 0.0373 (2) | 0.02325 (16) | 0.00336 (15) | 0.00968 (13) | 0.00198 (14) |
Cl1 | 0.0455 (5) | 0.0548 (5) | 0.0348 (4) | −0.0050 (4) | 0.0156 (3) | 0.0096 (3) |
Cl2 | 0.0441 (4) | 0.0534 (5) | 0.0370 (4) | 0.0117 (4) | 0.0156 (3) | −0.0055 (3) |
N1 | 0.0333 (13) | 0.0368 (13) | 0.0274 (11) | −0.0001 (11) | 0.0107 (10) | 0.0030 (10) |
N2 | 0.0328 (14) | 0.0442 (15) | 0.0308 (12) | −0.0071 (11) | 0.0059 (11) | 0.0059 (11) |
N3 | 0.0322 (13) | 0.0327 (12) | 0.0274 (11) | 0.0038 (10) | 0.0115 (10) | −0.0028 (10) |
N4 | 0.0353 (14) | 0.0460 (15) | 0.0315 (12) | 0.0111 (12) | 0.0070 (11) | −0.0011 (11) |
C1 | 0.0393 (17) | 0.0318 (16) | 0.0283 (14) | 0.0004 (13) | 0.0113 (13) | 0.0050 (12) |
C2 | 0.0446 (19) | 0.0457 (19) | 0.0443 (18) | 0.0033 (15) | 0.0161 (16) | −0.0013 (15) |
C3 | 0.060 (2) | 0.047 (2) | 0.057 (2) | 0.0065 (17) | 0.0307 (19) | −0.0037 (17) |
C4 | 0.070 (3) | 0.0408 (19) | 0.0428 (18) | −0.0004 (18) | 0.0219 (18) | −0.0054 (15) |
C5 | 0.057 (2) | 0.0387 (18) | 0.0338 (16) | −0.0094 (16) | 0.0108 (15) | 0.0011 (14) |
C6 | 0.0451 (17) | 0.0320 (15) | 0.0300 (14) | −0.0048 (13) | 0.0158 (13) | 0.0049 (12) |
C7 | 0.0386 (17) | 0.0348 (16) | 0.0295 (14) | −0.0009 (13) | 0.0108 (13) | 0.0105 (12) |
C8 | 0.0391 (17) | 0.0455 (18) | 0.0379 (16) | 0.0067 (14) | 0.0157 (14) | 0.0094 (14) |
C9 | 0.0315 (15) | 0.0423 (17) | 0.0338 (14) | −0.0009 (13) | 0.0158 (13) | 0.0042 (13) |
C10 | 0.0422 (18) | 0.0447 (18) | 0.0461 (18) | −0.0009 (15) | 0.0204 (15) | −0.0015 (15) |
C11 | 0.050 (2) | 0.071 (2) | 0.0388 (17) | −0.0070 (18) | 0.0226 (16) | −0.0099 (17) |
C12 | 0.082 (3) | 0.063 (2) | 0.048 (2) | −0.008 (2) | 0.039 (2) | 0.0066 (19) |
C13 | 0.128 (4) | 0.042 (2) | 0.074 (3) | −0.011 (2) | 0.068 (3) | 0.0020 (19) |
C14 | 0.090 (3) | 0.045 (2) | 0.051 (2) | −0.007 (2) | 0.046 (2) | −0.0031 (17) |
C15 | 0.0393 (17) | 0.0311 (15) | 0.0244 (13) | 0.0025 (12) | 0.0098 (12) | −0.0021 (11) |
C16 | 0.0424 (18) | 0.0462 (19) | 0.0371 (16) | −0.0024 (15) | 0.0136 (15) | 0.0003 (14) |
C17 | 0.060 (2) | 0.053 (2) | 0.0476 (19) | −0.0079 (18) | 0.0261 (18) | 0.0019 (16) |
C18 | 0.069 (2) | 0.048 (2) | 0.0374 (17) | −0.0019 (18) | 0.0191 (17) | 0.0089 (15) |
C19 | 0.065 (2) | 0.0432 (19) | 0.0290 (15) | 0.0116 (17) | 0.0093 (15) | 0.0058 (14) |
C20 | 0.0425 (17) | 0.0351 (16) | 0.0263 (13) | 0.0058 (14) | 0.0098 (13) | −0.0048 (12) |
C21 | 0.0366 (16) | 0.0332 (15) | 0.0263 (13) | 0.0073 (13) | 0.0068 (12) | −0.0050 (12) |
C22 | 0.0346 (16) | 0.0424 (18) | 0.0412 (16) | 0.0015 (14) | 0.0150 (14) | −0.0043 (14) |
C23 | 0.0336 (16) | 0.0444 (18) | 0.0359 (15) | 0.0056 (14) | 0.0145 (13) | −0.0059 (14) |
C24 | 0.047 (2) | 0.057 (2) | 0.0433 (18) | 0.0043 (16) | 0.0190 (16) | 0.0018 (15) |
C25 | 0.057 (2) | 0.098 (3) | 0.0372 (18) | 0.013 (2) | 0.0228 (17) | 0.001 (2) |
C26 | 0.077 (3) | 0.094 (3) | 0.045 (2) | 0.017 (3) | 0.023 (2) | −0.023 (2) |
C27 | 0.101 (4) | 0.055 (2) | 0.068 (3) | 0.010 (2) | 0.034 (3) | −0.018 (2) |
C28 | 0.079 (3) | 0.049 (2) | 0.0465 (19) | 0.0044 (19) | 0.030 (2) | −0.0064 (17) |
Zn1—N1 | 2.039 (2) | C9—C14 | 1.367 (4) |
Zn1—N3 | 2.044 (2) | C9—C10 | 1.370 (4) |
Zn1—Cl1 | 2.2575 (8) | C10—C11 | 1.389 (5) |
Zn1—Cl2 | 2.2626 (8) | C11—C12 | 1.358 (5) |
N1—C7 | 1.334 (4) | C12—C13 | 1.373 (5) |
N1—C1 | 1.407 (4) | C13—C14 | 1.393 (5) |
N2—C7 | 1.346 (4) | C15—C16 | 1.395 (4) |
N2—C6 | 1.383 (4) | C15—C20 | 1.399 (4) |
N3—C21 | 1.329 (4) | C16—C17 | 1.388 (4) |
N3—C15 | 1.405 (3) | C17—C18 | 1.384 (5) |
N4—C21 | 1.358 (4) | C18—C19 | 1.382 (5) |
N4—C20 | 1.375 (4) | C19—C20 | 1.398 (4) |
C1—C2 | 1.393 (4) | C21—C22 | 1.485 (4) |
C1—C6 | 1.400 (4) | C22—C23 | 1.519 (4) |
C2—C3 | 1.400 (4) | C23—C24 | 1.373 (4) |
C3—C4 | 1.391 (5) | C23—C28 | 1.383 (4) |
C4—C5 | 1.382 (5) | C24—C25 | 1.390 (5) |
C5—C6 | 1.387 (4) | C25—C26 | 1.366 (6) |
C7—C8 | 1.474 (4) | C26—C27 | 1.363 (5) |
C8—C9 | 1.527 (4) | C27—C28 | 1.392 (5) |
N1—Zn1—N3 | 108.54 (9) | C14—C9—C8 | 121.9 (3) |
N1—Zn1—Cl1 | 103.32 (7) | C10—C9—C8 | 119.4 (3) |
N3—Zn1—Cl1 | 116.67 (7) | C9—C10—C11 | 121.4 (3) |
N1—Zn1—Cl2 | 115.44 (7) | C12—C11—C10 | 119.7 (3) |
N3—Zn1—Cl2 | 104.47 (6) | C11—C12—C13 | 119.6 (3) |
Cl1—Zn1—Cl2 | 108.84 (3) | C12—C13—C14 | 120.5 (3) |
C7—N1—C1 | 106.0 (2) | C9—C14—C13 | 120.2 (3) |
C7—N1—Zn1 | 130.8 (2) | C16—C15—C20 | 121.2 (3) |
C1—N1—Zn1 | 121.27 (19) | C16—C15—N3 | 130.4 (3) |
C7—N2—C6 | 109.1 (2) | C20—C15—N3 | 108.4 (2) |
C21—N3—C15 | 106.3 (2) | C17—C16—C15 | 116.3 (3) |
C21—N3—Zn1 | 130.9 (2) | C18—C17—C16 | 122.4 (3) |
C15—N3—Zn1 | 121.73 (18) | C19—C18—C17 | 122.0 (3) |
C21—N4—C20 | 108.6 (2) | C18—C19—C20 | 116.2 (3) |
C2—C1—C6 | 120.9 (3) | N4—C20—C19 | 132.4 (3) |
C2—C1—N1 | 130.4 (3) | N4—C20—C15 | 105.7 (2) |
C6—C1—N1 | 108.6 (3) | C19—C20—C15 | 121.9 (3) |
C1—C2—C3 | 116.2 (3) | N3—C21—N4 | 111.0 (3) |
C4—C3—C2 | 122.2 (3) | N3—C21—C22 | 126.7 (3) |
C5—C4—C3 | 121.5 (3) | N4—C21—C22 | 122.3 (3) |
C4—C5—C6 | 116.6 (3) | C21—C22—C23 | 114.2 (2) |
N2—C6—C5 | 132.4 (3) | C24—C23—C28 | 118.4 (3) |
N2—C6—C1 | 105.1 (2) | C24—C23—C22 | 119.2 (3) |
C5—C6—C1 | 122.5 (3) | C28—C23—C22 | 122.3 (3) |
N1—C7—N2 | 111.1 (3) | C23—C24—C25 | 121.0 (4) |
N1—C7—C8 | 125.7 (3) | C26—C25—C24 | 120.3 (4) |
N2—C7—C8 | 123.2 (3) | C27—C26—C25 | 119.2 (3) |
C7—C8—C9 | 115.3 (2) | C26—C27—C28 | 121.0 (4) |
C14—C9—C10 | 118.7 (3) | C23—C28—C27 | 120.0 (3) |
N3—Zn1—N1—C7 | −127.2 (2) | C9—C10—C11—C12 | −0.7 (5) |
Cl1—Zn1—N1—C7 | 108.4 (2) | C10—C11—C12—C13 | 0.1 (6) |
Cl2—Zn1—N1—C7 | −10.3 (3) | C11—C12—C13—C14 | 0.2 (7) |
N3—Zn1—N1—C1 | 71.1 (2) | C10—C9—C14—C13 | −0.8 (6) |
Cl1—Zn1—N1—C1 | −53.4 (2) | C8—C9—C14—C13 | 177.8 (4) |
Cl2—Zn1—N1—C1 | −172.09 (18) | C12—C13—C14—C9 | 0.2 (7) |
N1—Zn1—N3—C21 | −124.5 (2) | C21—N3—C15—C16 | −178.9 (3) |
Cl1—Zn1—N3—C21 | −8.3 (3) | Zn1—N3—C15—C16 | −9.6 (4) |
Cl2—Zn1—N3—C21 | 111.9 (2) | C21—N3—C15—C20 | 0.4 (3) |
N1—Zn1—N3—C15 | 69.1 (2) | Zn1—N3—C15—C20 | 169.74 (18) |
Cl1—Zn1—N3—C15 | −174.72 (17) | C20—C15—C16—C17 | 1.3 (4) |
Cl2—Zn1—N3—C15 | −54.5 (2) | N3—C15—C16—C17 | −179.4 (3) |
C7—N1—C1—C2 | −178.7 (3) | C15—C16—C17—C18 | 0.2 (5) |
Zn1—N1—C1—C2 | −13.0 (4) | C16—C17—C18—C19 | −1.3 (5) |
C7—N1—C1—C6 | −0.3 (3) | C17—C18—C19—C20 | 0.8 (5) |
Zn1—N1—C1—C6 | 165.41 (18) | C21—N4—C20—C19 | −178.7 (3) |
C6—C1—C2—C3 | 0.7 (4) | C21—N4—C20—C15 | 0.7 (3) |
N1—C1—C2—C3 | 178.9 (3) | C18—C19—C20—N4 | −180.0 (3) |
C1—C2—C3—C4 | −0.3 (5) | C18—C19—C20—C15 | 0.7 (4) |
C2—C3—C4—C5 | −0.2 (5) | C16—C15—C20—N4 | 178.7 (3) |
C3—C4—C5—C6 | 0.3 (5) | N3—C15—C20—N4 | −0.7 (3) |
C7—N2—C6—C5 | 179.0 (3) | C16—C15—C20—C19 | −1.8 (4) |
C7—N2—C6—C1 | −0.8 (3) | N3—C15—C20—C19 | 178.8 (3) |
C4—C5—C6—N2 | −179.7 (3) | C15—N3—C21—N4 | 0.0 (3) |
C4—C5—C6—C1 | 0.0 (4) | Zn1—N3—C21—N4 | −167.94 (18) |
C2—C1—C6—N2 | 179.2 (3) | C15—N3—C21—C22 | −177.5 (3) |
N1—C1—C6—N2 | 0.7 (3) | Zn1—N3—C21—C22 | 14.5 (4) |
C2—C1—C6—C5 | −0.6 (4) | C20—N4—C21—N3 | −0.5 (3) |
N1—C1—C6—C5 | −179.1 (3) | C20—N4—C21—C22 | 177.2 (2) |
C1—N1—C7—N2 | −0.2 (3) | N3—C21—C22—C23 | 86.8 (4) |
Zn1—N1—C7—N2 | −164.03 (18) | N4—C21—C22—C23 | −90.6 (3) |
C1—N1—C7—C8 | 180.0 (3) | C21—C22—C23—C24 | −151.6 (3) |
Zn1—N1—C7—C8 | 16.1 (4) | C21—C22—C23—C28 | 29.1 (4) |
C6—N2—C7—N1 | 0.6 (3) | C28—C23—C24—C25 | 0.5 (5) |
C6—N2—C7—C8 | −179.5 (2) | C22—C23—C24—C25 | −178.9 (3) |
N1—C7—C8—C9 | 81.8 (4) | C23—C24—C25—C26 | 0.6 (6) |
N2—C7—C8—C9 | −98.0 (3) | C24—C25—C26—C27 | −1.2 (6) |
C7—C8—C9—C14 | 30.9 (5) | C25—C26—C27—C28 | 0.7 (7) |
C7—C8—C9—C10 | −150.5 (3) | C24—C23—C28—C27 | −0.9 (6) |
C14—C9—C10—C11 | 1.0 (5) | C22—C23—C28—C27 | 178.4 (3) |
C8—C9—C10—C11 | −177.7 (3) | C26—C27—C28—C23 | 0.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl2i | 0.86 | 2.46 | 3.240 (3) | 152 |
N4—H4A···Cl1ii | 0.86 | 2.55 | 3.314 (3) | 148 |
C8—H8A···Cl2 | 0.97 | 2.81 | 3.594 (3) | 138 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [ZnCl2(C14H12N2)2] |
Mr | 552.78 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 11.8623 (2), 16.3674 (1), 14.1767 (2) |
β (°) | 111.943 (1) |
V (Å3) | 2553.08 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.20 |
Crystal size (mm) | 0.28 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.731, 0.796 |
No. of measured, independent and observed [I > 2σ(I)'] reflections | 17665, 6226, 3898 |
Rint | 0.073 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.133, 0.93 |
No. of reflections | 6226 |
No. of parameters | 316 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.74, −1.51 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL and PLATON (Spek, 1990).
Zn1—N1 | 2.039 (2) | Zn1—Cl1 | 2.2575 (8) |
Zn1—N3 | 2.044 (2) | Zn1—Cl2 | 2.2626 (8) |
N1—Zn1—N3 | 108.54 (9) | N1—Zn1—Cl2 | 115.44 (7) |
N1—Zn1—Cl1 | 103.32 (7) | N3—Zn1—Cl2 | 104.47 (6) |
N3—Zn1—Cl1 | 116.67 (7) | Cl1—Zn1—Cl2 | 108.84 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl2i | 0.86 | 2.46 | 3.240 (3) | 152 |
N4—H4A···Cl1ii | 0.86 | 2.55 | 3.314 (3) | 148 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |
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Benzimidazole is an interesting heterocyclic ring because it is present in various naturally occurring drugs, such as omeprazole, astemizole and emedastine difumarate (Sakai et al., 1989). The efficacy of substituted benzimidazoles in the treatment of parasitic infections is well known (Brown et al., 1961; Preston, 1974; Sarkar et al., 1984). Benzimidazole-substituted moieties are established pharmacophores in parasitic chemotherapy. Bis(2-benzimidazoles) and some substituted bis(2-benzimidazolyl)alkanes have attracted much interest because of their wide-ranging antiviral activity (Tidwell, et al., 1993) and also because of the coordination chemistry of azoles acting as ligands in transition-metal compounds. Such compounds are increasingly being studied in the context of modelling biological systems (Pujar et al., 1988; Bouwman et al., 1990). Zinc is a relatively abundant element in biological organisms and plays an essential role in a large number of enzymatic reactions (Liljas et al., 1972). Zinc(II), being a d10 ion, provides few spectroscopic signatures for the monitoring of structure. The structure of the zinc binding site can only be elucidated by X-ray crystallography. \scheme I
In the title compound, (I), the molecule possesses near C2 symmetry and the symmetry axis lies parallel to the b axis. The Zn atom is coordinated tetrahedrally by two Cl anions and two 2-benzyl-1H-benzimidazole ligands, i.e. ZnCl2N2. The ZnCl2N2 tetrahedron is slightly distorted, with angles ranging from 103.32 (7) to 116.67 (7) Å. The range of the tetrahedral angles are comparable with the corresponding values in the reported complex ZnCl2(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine)2 [102.09 (9)–117.54 (4) Å; Salas et al., 1994] but the coordination around Zn in another complex, which also contains the ZnCl2N2 unit, namely ZnCl2[purine]2 (Laity & Taylor, 1995), is severely distorted compared with the title complex, with the angles ranging from 99.9 (1) to 113.7 (1) Å. \scheme
The average Zn—Cl distance of 2.261 (1) Å is longer than the average corresponding distances reported for related metal complexes with distorted ZnN2Cl2 tetrahedral environments, cf. 2.224 (1) Å in ZnCl2(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine)2 (Salas et al., 1994), 2.212 (4) Å in ZnCl2(2,9-dimethyl-1,10-phenanthroline) (Preston & Kennard, 1969), 2.226 (2) Å in ZnCl2(purine)2 (Laity & Taylor, 1995) and 2.209 (3) Å in ZnCl2(4-vinylpyridine)2 (Steffen & Palenik, 1977), but comparable to 2.255 (1) Å in ZnCl2[1-(5,6-dimethyl-1H-benzimidazolyl)- 3-(1,3-benzimidazolyl)-2-thiapropane] (Matthews et al., 1998).
The average Zn—N bond distance of 2.042 (3) Å is comparable to the reported average values, e.g. 2.039 (3) Å in ZnCl2(5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine)2 (Salas et al., 1994), 2.05 (1) Å in ZnCl2(1-methyltetrazole)2 (Baenziger & Schultz, 1971), 2.059 (3) Å in ZnCl2(1-methylcytosine)2 (Beauchamp, 1984) and 2.027 (3) Å in ZnCl2[1-(5,6-dimethyl-1H-benzimidazolyl)-3-benzimidazolyl-2-thiapropane] (Matthews et al., 1998), but longer than the average value of 2.007 (4) Å in Zn0.99Cu0.01Cl2[1,2-dimethylimidazole]2 (Bharadwaj et al., 1991).
The dihedral angles between the benzimidazole moieties (involving N1/N2 and N3/N4) and the phenyl rings (C9–C14 and C23–C28) are 83.0 (2) and 79.4 (2)°, respectively. The mean planes of the two benzimidazole moieties form a dihedral angle of 69.7 (1)°, while the dihedral angle between the phenyl rings is 1.2 (2)°.
In the crystal, the N atoms (N2 and N4) from both benzimidazole moieties are involved in N—H···Cl intermolecular hydrogen bonds with the Cl atoms (Table 2). These intermolecular hydrogen bonds link the molecules into infinite one-dimensional chains in the [101] direction.