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In the title compound, C20H14Cl2N2, the dihedral angles formed by the benzimidazole ring with the benzene rings of the 4-chlorobenzyl and the 4-chlorophenyl groups are 88.15 (8) and 33.4 (1)°, respectively. The mol­ecules are linked by C—H...Cl hydrogen bonds, forming a C(12) chain along the [010] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038871/at2364sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038871/at2364Isup2.hkl
Contains datablock I

CCDC reference: 654269

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.086
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 2749 Count of symmetry unique reflns 1647 Completeness (_total/calc) 166.91% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1102 Fraction of Friedel pairs measured 0.669 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 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 2 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

Comment top

Benzimidazole derivatives display wide-ranging biological activities, such as as inhibitors of hepatitis C virus NS5B polymerase (Ishida et al., 2006) and heparanase (Xu et al., 2006) and antimicrobial activities (Özden et al., 2005). The crystal structures of some benzimidazole derivatives have been previously reported (Yang et al., 2007). Here we report the crystal structure of a new benzimidazole derivative, 2-(4-chlorophenyl)-1-[(4-chlorophenyl)methyl]-1H benzimidazole, (I).

In the molecule of compound (I) (Fig. 1), the benzene ring C9—C14 is approximately perpendicular to the benzimidazole ring. The dihedral angles enclosed by the benzimidazole ring with the benzene rings C9–C14 and benzene ring C15–C20 are 88.15 (8)° and 33.4 (1)°, respectively. The geometrical parameters for (I) are normal.

In the crystal structure of (I), the C11 atom in the molecule at (x, y, z) acts as hydrogen-bond donor, to the Cl1 atom in the molecule at (1 - x, 3/2 + y, 1 - z), the molecules are linked through C—H···Cl hydrogen bonds, forming a C(12) chain (Bernstein et al., 1995) along the [010] direction (Fig. 2 and Table 1).

Related literature top

For related literature, see: Bernstein et al. (1995); Ishida et al. (2006); Özden et al. (2005); Xu et al. (2006); Yang et al. (2007).

Experimental top

The reaction mixture containing 4-chlorobenzaldehyde (2.80 g, 20 mmol) and o-phenylene diamine (1.08 g, 10 mmol) was refluxed for about 4 h in ethanol (30 ml), then cooled and the product filtered off, washed with ethanol and dried. Yellow crystals of (I) suitable for X-ray structure analysis were obtained by recrystallizing the crude product from ethanol (m.p. 450–452 K).

Refinement top

All H atoms were positioned geometrically and refined as riding on their parent atoms, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C) for all H atoms.

Structure description top

Benzimidazole derivatives display wide-ranging biological activities, such as as inhibitors of hepatitis C virus NS5B polymerase (Ishida et al., 2006) and heparanase (Xu et al., 2006) and antimicrobial activities (Özden et al., 2005). The crystal structures of some benzimidazole derivatives have been previously reported (Yang et al., 2007). Here we report the crystal structure of a new benzimidazole derivative, 2-(4-chlorophenyl)-1-[(4-chlorophenyl)methyl]-1H benzimidazole, (I).

In the molecule of compound (I) (Fig. 1), the benzene ring C9—C14 is approximately perpendicular to the benzimidazole ring. The dihedral angles enclosed by the benzimidazole ring with the benzene rings C9–C14 and benzene ring C15–C20 are 88.15 (8)° and 33.4 (1)°, respectively. The geometrical parameters for (I) are normal.

In the crystal structure of (I), the C11 atom in the molecule at (x, y, z) acts as hydrogen-bond donor, to the Cl1 atom in the molecule at (1 - x, 3/2 + y, 1 - z), the molecules are linked through C—H···Cl hydrogen bonds, forming a C(12) chain (Bernstein et al., 1995) along the [010] direction (Fig. 2 and Table 1).

For related literature, see: Bernstein et al. (1995); Ishida et al. (2006); Özden et al. (2005); Xu et al. (2006); Yang et al. (2007).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing the formation of a C(12) chain along the [010] direction. For clarity, the H atoms not involved in the motif shown have been omitted. [Symmetry codes: (*) 1 - x, 3/2 + y, 1 - z; (&) 1 - x, -3/2 + y, 1 - z]. Dashed lines indicate hydrogen bonds.
1-(4-Chlorobenzyl)-2-(4-chlorophenyl)-1H-benzimidazole top
Crystal data top
C20H14Cl2N2F(000) = 364
Mr = 353.23Dx = 1.399 Mg m3
Monoclinic, P21Melting point: 450 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 11.6427 (17) ÅCell parameters from 1152 reflections
b = 5.4420 (7) Åθ = 2.3–21.3°
c = 13.2339 (19) ŵ = 0.39 mm1
β = 90.936 (2)°T = 298 K
V = 838.4 (2) Å3Plate, yellow
Z = 20.48 × 0.23 × 0.15 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2749 independent reflections
Radiation source: fine-focus sealed tube1744 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1013
Tmin = 0.835, Tmax = 0.944k = 66
4248 measured reflectionsl = 1515
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)] = 0.042H-atom parameters constrained
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0295P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2749 reflectionsΔρmax = 0.23 e Å3
217 parametersΔρmin = 0.19 e Å3
1 restraintAbsolute structure: Flack (1983), 1102 Freidel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (8)
Crystal data top
C20H14Cl2N2V = 838.4 (2) Å3
Mr = 353.23Z = 2
Monoclinic, P21Mo Kα radiation
a = 11.6427 (17) ŵ = 0.39 mm1
b = 5.4420 (7) ÅT = 298 K
c = 13.2339 (19) Å0.48 × 0.23 × 0.15 mm
β = 90.936 (2)°
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2749 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1744 reflections with I > 2σ(I)
Tmin = 0.835, Tmax = 0.944Rint = 0.029
4248 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.086Δρmax = 0.23 e Å3
S = 1.02Δρmin = 0.19 e Å3
2749 reflectionsAbsolute structure: Flack (1983), 1102 Freidel pairs
217 parametersAbsolute structure parameter: 0.01 (8)
1 restraint
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.33404 (9)0.0815 (2)0.63346 (7)0.0884 (4)
Cl20.75909 (8)1.0489 (3)0.12846 (9)0.1146 (5)
N10.2015 (2)0.8712 (5)0.24471 (19)0.0480 (7)
N20.0955 (2)1.0188 (6)0.3711 (2)0.0587 (8)
C10.1724 (3)0.8546 (7)0.3452 (2)0.0481 (9)
C20.0722 (3)1.1501 (6)0.2833 (3)0.0549 (10)
C30.1370 (2)1.0590 (7)0.2042 (2)0.0499 (8)
C40.1289 (3)1.1528 (7)0.1067 (3)0.0618 (10)
H40.17221.08920.05430.074*
C50.0540 (3)1.3436 (8)0.0918 (3)0.0710 (12)
H50.04571.41070.02740.085*
C60.0100 (3)1.4397 (8)0.1699 (4)0.0788 (13)
H60.05921.57100.15680.095*
C70.0027 (3)1.3453 (8)0.2671 (3)0.0698 (11)
H70.04601.40990.31920.084*
C80.2738 (3)0.7104 (6)0.1855 (2)0.0545 (9)
H8A0.23840.68830.11930.065*
H8B0.27720.55070.21800.065*
C90.3948 (3)0.8033 (6)0.1723 (2)0.0439 (8)
C100.4364 (3)1.0114 (7)0.2183 (2)0.0596 (10)
H100.38891.10360.25950.071*
C110.5489 (3)1.0852 (8)0.2038 (3)0.0680 (10)
H110.57641.22710.23500.082*
C120.6190 (3)0.9516 (8)0.1443 (3)0.0657 (11)
C130.5794 (3)0.7433 (8)0.0987 (3)0.0681 (11)
H130.62780.65000.05870.082*
C140.4680 (3)0.6721 (6)0.1120 (2)0.0579 (10)
H140.44100.53150.07950.069*
C150.2178 (3)0.6688 (6)0.4160 (2)0.0506 (9)
C160.3296 (3)0.5778 (8)0.4130 (2)0.0588 (9)
H160.38030.63790.36530.071*
C170.3657 (3)0.3989 (7)0.4805 (3)0.0642 (11)
H170.43970.33570.47720.077*
C180.2917 (3)0.3150 (7)0.5521 (2)0.0579 (10)
C190.1828 (3)0.4092 (7)0.5594 (3)0.0609 (10)
H190.13390.35470.60960.073*
C200.1469 (3)0.5865 (8)0.4911 (2)0.0587 (9)
H200.07340.65150.49590.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1053 (8)0.0830 (8)0.0764 (6)0.0009 (8)0.0143 (6)0.0255 (6)
Cl20.0583 (6)0.1482 (13)0.1377 (9)0.0234 (9)0.0129 (6)0.0186 (10)
N10.0442 (16)0.049 (2)0.0513 (17)0.0001 (15)0.0003 (13)0.0016 (16)
N20.0527 (17)0.062 (2)0.0609 (18)0.0069 (18)0.0037 (15)0.0004 (17)
C10.041 (2)0.052 (2)0.051 (2)0.0077 (19)0.0021 (17)0.0018 (19)
C20.042 (2)0.055 (3)0.067 (2)0.0033 (19)0.0052 (19)0.001 (2)
C30.0389 (18)0.048 (2)0.063 (2)0.006 (2)0.0093 (17)0.002 (2)
C40.056 (2)0.065 (3)0.064 (2)0.012 (2)0.0116 (18)0.007 (2)
C50.062 (3)0.066 (3)0.084 (3)0.012 (2)0.022 (2)0.019 (3)
C60.057 (3)0.061 (3)0.118 (4)0.002 (2)0.027 (3)0.014 (3)
C70.054 (2)0.063 (3)0.092 (3)0.006 (2)0.002 (2)0.005 (2)
C80.060 (2)0.050 (2)0.053 (2)0.006 (2)0.0035 (18)0.0054 (18)
C90.048 (2)0.043 (2)0.0409 (18)0.0019 (18)0.0019 (16)0.0008 (17)
C100.059 (2)0.052 (3)0.068 (2)0.004 (2)0.0028 (19)0.013 (2)
C110.062 (2)0.055 (3)0.086 (3)0.022 (2)0.004 (2)0.010 (2)
C120.052 (2)0.080 (3)0.065 (3)0.002 (2)0.004 (2)0.013 (2)
C130.067 (3)0.074 (3)0.063 (2)0.008 (2)0.013 (2)0.003 (2)
C140.069 (2)0.054 (3)0.051 (2)0.003 (2)0.0039 (19)0.0112 (18)
C150.052 (2)0.054 (3)0.0457 (19)0.0022 (19)0.0030 (17)0.0044 (18)
C160.048 (2)0.067 (3)0.061 (2)0.001 (2)0.0053 (17)0.012 (2)
C170.054 (2)0.069 (3)0.069 (2)0.009 (2)0.002 (2)0.005 (2)
C180.066 (2)0.058 (3)0.049 (2)0.004 (2)0.0115 (19)0.005 (2)
C190.061 (2)0.069 (3)0.052 (2)0.010 (2)0.0045 (19)0.003 (2)
C200.050 (2)0.073 (3)0.053 (2)0.003 (2)0.0017 (17)0.005 (2)
Geometric parameters (Å, º) top
Cl1—C181.732 (4)C9—C101.371 (4)
Cl2—C121.731 (4)C9—C141.377 (4)
N1—C31.373 (4)C10—C111.387 (4)
N1—C11.381 (3)C10—H100.9300
N1—C81.453 (4)C11—C121.354 (5)
N2—C11.314 (4)C11—H110.9300
N2—C21.387 (4)C12—C131.361 (5)
C1—C151.471 (4)C13—C141.368 (4)
C2—C71.388 (5)C13—H130.9300
C2—C31.392 (4)C14—H140.9300
C3—C41.389 (4)C15—C201.376 (4)
C4—C51.369 (5)C15—C161.394 (4)
C4—H40.9300C16—C171.382 (5)
C5—C61.387 (5)C16—H160.9300
C5—H50.9300C17—C181.369 (4)
C6—C71.386 (5)C17—H170.9300
C6—H60.9300C18—C191.373 (4)
C7—H70.9300C19—C201.382 (5)
C8—C91.509 (4)C19—H190.9300
C8—H8A0.9700C20—H200.9300
C8—H8B0.9700
C3—N1—C1106.5 (3)C9—C10—C11120.4 (3)
C3—N1—C8123.8 (3)C9—C10—H10119.8
C1—N1—C8129.3 (3)C11—C10—H10119.8
C1—N2—C2104.9 (3)C12—C11—C10120.3 (4)
N2—C1—N1112.7 (3)C12—C11—H11119.8
N2—C1—C15122.8 (3)C10—C11—H11119.8
N1—C1—C15124.5 (3)C11—C12—C13120.1 (4)
N2—C2—C7129.6 (4)C11—C12—Cl2119.0 (4)
N2—C2—C3110.2 (3)C13—C12—Cl2120.9 (3)
C7—C2—C3120.2 (3)C12—C13—C14119.6 (4)
N1—C3—C4131.7 (3)C12—C13—H13120.2
N1—C3—C2105.7 (3)C14—C13—H13120.2
C4—C3—C2122.6 (4)C13—C14—C9121.7 (3)
C5—C4—C3116.5 (4)C13—C14—H14119.2
C5—C4—H4121.8C9—C14—H14119.2
C3—C4—H4121.8C20—C15—C16118.4 (3)
C4—C5—C6121.9 (4)C20—C15—C1118.0 (3)
C4—C5—H5119.1C16—C15—C1123.5 (3)
C6—C5—H5119.1C17—C16—C15120.4 (3)
C7—C6—C5121.7 (4)C17—C16—H16119.8
C7—C6—H6119.1C15—C16—H16119.8
C5—C6—H6119.1C18—C17—C16119.6 (3)
C6—C7—C2117.2 (4)C18—C17—H17120.2
C6—C7—H7121.4C16—C17—H17120.2
C2—C7—H7121.4C17—C18—C19121.1 (3)
N1—C8—C9114.2 (3)C17—C18—Cl1119.9 (3)
N1—C8—H8A108.7C19—C18—Cl1118.9 (3)
C9—C8—H8A108.7C18—C19—C20118.9 (3)
N1—C8—H8B108.7C18—C19—H19120.5
C9—C8—H8B108.7C20—C19—H19120.5
H8A—C8—H8B107.6C15—C20—C19121.4 (3)
C10—C9—C14117.9 (3)C15—C20—H20119.3
C10—C9—C8123.4 (3)C19—C20—H20119.3
C14—C9—C8118.7 (3)
C2—N2—C1—N10.3 (4)N1—C8—C9—C14175.9 (3)
C2—N2—C1—C15177.5 (3)C14—C9—C10—C110.1 (5)
C3—N1—C1—N20.6 (3)C8—C9—C10—C11179.3 (3)
C8—N1—C1—N2173.5 (3)C9—C10—C11—C120.4 (5)
C3—N1—C1—C15177.1 (3)C10—C11—C12—C130.2 (5)
C8—N1—C1—C154.3 (5)C10—C11—C12—Cl2179.7 (3)
C1—N2—C2—C7180.0 (3)C11—C12—C13—C141.0 (6)
C1—N2—C2—C30.2 (4)Cl2—C12—C13—C14179.5 (3)
C1—N1—C3—C4178.3 (3)C12—C13—C14—C91.3 (5)
C8—N1—C3—C45.0 (5)C10—C9—C14—C130.8 (5)
C1—N1—C3—C20.7 (3)C8—C9—C14—C13178.5 (3)
C8—N1—C3—C2174.0 (3)N2—C1—C15—C2030.5 (5)
N2—C2—C3—N10.6 (3)N1—C1—C15—C20147.0 (3)
C7—C2—C3—N1179.6 (3)N2—C1—C15—C16147.4 (3)
N2—C2—C3—C4178.5 (3)N1—C1—C15—C1635.1 (5)
C7—C2—C3—C41.3 (5)C20—C15—C16—C173.7 (5)
N1—C3—C4—C5179.5 (3)C1—C15—C16—C17178.4 (3)
C2—C3—C4—C50.6 (5)C15—C16—C17—C181.5 (5)
C3—C4—C5—C60.4 (5)C16—C17—C18—C191.3 (5)
C4—C5—C6—C70.9 (6)C16—C17—C18—Cl1177.3 (3)
C5—C6—C7—C20.3 (5)C17—C18—C19—C201.9 (5)
N2—C2—C7—C6179.0 (3)Cl1—C18—C19—C20176.7 (3)
C3—C2—C7—C60.8 (5)C16—C15—C20—C193.1 (5)
C3—N1—C8—C988.7 (3)C1—C15—C20—C19178.9 (3)
C1—N1—C8—C999.6 (4)C18—C19—C20—C150.3 (5)
N1—C8—C9—C104.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···Cl1i0.932.793.701 (4)167
Symmetry code: (i) x+1, y+3/2, z+1.

Experimental details

Crystal data
Chemical formulaC20H14Cl2N2
Mr353.23
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)11.6427 (17), 5.4420 (7), 13.2339 (19)
β (°) 90.936 (2)
V3)838.4 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.39
Crystal size (mm)0.48 × 0.23 × 0.15
Data collection
DiffractometerSiemens SMART 1000 CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.835, 0.944
No. of measured, independent and
observed [I > 2σ(I)] reflections
4248, 2749, 1744
Rint0.029
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.086, 1.02
No. of reflections2749
No. of parameters217
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.19
Absolute structureFlack (1983), 1102 Freidel pairs
Absolute structure parameter0.01 (8)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···Cl1i0.932.793.701 (4)166.8
Symmetry code: (i) x+1, y+3/2, z+1.
 

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