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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o316.
Published online 2009 January 14. doi:  10.1107/S1600536809001238
PMCID: PMC2968276

1-Benzyl-2-phenyl-1H-benzimidazole

Abstract

The title compound, C20H16N2, has been synthesized by the reaction of benzaldehyde with o-phenyl­endiamine and l-proline. The benzimidazole group makes a dihedral angle of 29.04 (1)° with the attached benzene ring, and is approximately perpendicular to the plane of the benzyl group [dihedral angle = 88.9 (1)°] The crystal packing exhibits no unusually short inter­molecular contacts.

Related literature

For background literature concerning benzimidazole compounds, see: Zarrinmayeh et al. (1998 [triangle]); Spasov et al. (1999 [triangle]). For a related structure, see: Yang et al. (2007 [triangle]).

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Object name is e-65-0o316-scheme1.jpg

Experimental

Crystal data

  • C20H16N2
  • M r = 284.35
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o316-efi1.jpg
  • a = 6.338 (3) Å
  • b = 8.085 (3) Å
  • c = 30.190 (12) Å
  • V = 1547.0 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 298 (2) K
  • 0.63 × 0.55 × 0.47 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.956, T max = 0.967
  • 6729 measured reflections
  • 1631 independent reflections
  • 1221 reflections with I > 2σ(I)
  • R int = 0.073

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.115
  • S = 1.14
  • 1631 reflections
  • 199 parameters
  • H-atom parameters constrained
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001238/bi2334sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001238/bi2334Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. DCLG2008002).

supplementary crystallographic information

Comment

The benzimidazole group is of significant importance in medicinal chemistry. Several publications report benzimidazole-containing compounds showing biological activities such as selective neuropeptide receptor antagonism (Zarrinmayeh, et al.,1998). Substituted benzimidazole derivatives have found commercial applications in veterinary medicine as anthelmintic agents and in diverse human therapeutic areas such as treatment of ulcers and as antihistaminics (Spasov, et al.,1999).

In the crystal structure of the title compound, the imidazole ring is almost coplanar with the benzene ring (C2/C3/C4/C5/C6/C7): the C1—N1—C3—C2 and C1—N2—C2—C3 torsion angles are 0.0 (3)° and -0.8 (3)°, respectively. The dihedral angles between the imidazole ring and the benzene rings (C2/C3/C4/C5/C6/C7) and (C15/C16/C17/C18/C19/C20) are 2.84 (1)° and 29.54 (1)°, respectively. There are no significantly short intermolecular contacts.

Experimental

o-Phenylendiamine (5 mmol), benzaldehyde (10 mmol), L-proline (1 mmol) and 10 ml ethanol were mixed in a 50 ml flask. After stirring for 4 h at 373 K, the resulting mixture was recrystalized from ethanol, affording the title compound as an orange crystalline solid. Elemental analysis calculated: C 84.48, H 5.67, N 9.85%; found: C 84.38, H 5.54, N 9.77%.

Refinement

H atoms were placed in geometrically idealized positions (methylene C—H = 0.97 Å, aromatic C—H = 0.93 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2Ueq(C). In the absence of significant anomalous scattering, Friedel pairs have been merged as equivalent data.

Figures

Fig. 1.
Molecular structure showing 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C20H16N2F(000) = 600
Mr = 284.35Dx = 1.221 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1704 reflections
a = 6.338 (3) Åθ = 2.6–21.8°
b = 8.085 (3) ŵ = 0.07 mm1
c = 30.190 (12) ÅT = 298 K
V = 1547.0 (10) Å3Block, orange
Z = 40.63 × 0.55 × 0.47 mm

Data collection

Bruker SMART CCD diffractometer1631 independent reflections
Radiation source: fine-focus sealed tube1221 reflections with I > 2σ(I)
graphiteRint = 0.073
[var phi] and ω scansθmax = 25.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→7
Tmin = 0.956, Tmax = 0.967k = −9→7
6729 measured reflectionsl = −26→36

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.14w = 1/[σ2(Fo2) + (0.0509P)2] where P = (Fo2 + 2Fc2)/3
1631 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = −0.16 e Å3

Special details

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)

xyzUiso*/Ueq
N10.2537 (4)−0.0386 (3)0.13584 (8)0.0404 (6)
N20.5764 (4)−0.1478 (3)0.14294 (9)0.0457 (7)
C10.4421 (5)−0.0765 (3)0.11598 (10)0.0383 (7)
C20.4713 (5)−0.1607 (3)0.18323 (11)0.0421 (8)
C30.2703 (5)−0.0923 (3)0.17932 (10)0.0406 (7)
C40.1274 (6)−0.0905 (4)0.21384 (12)0.0543 (9)
H4−0.0051−0.04220.21100.065*
C50.1920 (7)−0.1639 (5)0.25254 (13)0.0678 (11)
H50.1002−0.16670.27660.081*
C60.3909 (7)−0.2340 (5)0.25674 (13)0.0683 (12)
H60.4288−0.28240.28350.082*
C70.5324 (7)−0.2341 (4)0.22272 (12)0.0588 (10)
H70.6651−0.28160.22590.071*
C80.0616 (5)0.0304 (4)0.11706 (11)0.0422 (8)
H8A−0.0587−0.02900.12900.051*
H8B0.06300.01340.08530.051*
C90.0341 (5)0.2130 (3)0.12639 (10)0.0352 (7)
C100.1930 (5)0.3114 (4)0.14264 (11)0.0484 (9)
H100.32500.26560.14820.058*
C110.1592 (6)0.4782 (4)0.15079 (13)0.0574 (10)
H110.26800.54300.16200.069*
C12−0.0329 (6)0.5478 (4)0.14239 (12)0.0551 (9)
H12−0.05500.65970.14770.066*
C13−0.1927 (6)0.4519 (4)0.12605 (12)0.0559 (10)
H13−0.32390.49880.12030.067*
C14−0.1601 (5)0.2856 (4)0.11803 (11)0.0479 (9)
H14−0.26980.22150.10690.057*
C150.4924 (5)−0.0445 (4)0.06922 (10)0.0422 (8)
C160.6356 (5)−0.1483 (4)0.04824 (12)0.0538 (9)
H160.6957−0.23510.06400.065*
C170.6904 (6)−0.1255 (6)0.00461 (13)0.0721 (12)
H170.7854−0.1972−0.00890.087*
C180.6052 (7)0.0028 (5)−0.01897 (14)0.0737 (13)
H180.63980.0174−0.04870.088*
C190.4695 (7)0.1087 (5)0.00140 (12)0.0730 (12)
H190.41470.1976−0.01440.088*
C200.4119 (6)0.0867 (4)0.04484 (11)0.0555 (9)
H200.31830.16030.05800.067*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0385 (15)0.0347 (14)0.0479 (17)0.0033 (12)−0.0049 (14)−0.0007 (12)
N20.0378 (14)0.0455 (16)0.0537 (17)0.0033 (13)−0.0038 (14)0.0020 (13)
C10.0364 (17)0.0306 (16)0.0480 (18)0.0017 (14)−0.0020 (16)−0.0081 (13)
C20.0455 (19)0.0329 (16)0.048 (2)−0.0025 (15)−0.0023 (17)−0.0001 (14)
C30.0487 (19)0.0315 (16)0.0416 (19)−0.0025 (15)−0.0015 (16)0.0004 (14)
C40.058 (2)0.051 (2)0.054 (2)0.0026 (18)0.0044 (19)−0.0065 (18)
C50.082 (3)0.075 (3)0.047 (2)−0.008 (3)0.014 (2)−0.0034 (19)
C60.087 (3)0.070 (3)0.048 (2)−0.006 (2)−0.012 (2)0.0142 (19)
C70.062 (2)0.054 (2)0.061 (2)0.0028 (19)−0.012 (2)0.0057 (18)
C80.0329 (16)0.0359 (16)0.058 (2)0.0006 (13)−0.0057 (15)−0.0050 (14)
C90.0362 (16)0.0308 (15)0.0386 (16)−0.0016 (13)0.0000 (15)0.0013 (12)
C100.0438 (19)0.0394 (19)0.062 (2)−0.0019 (15)−0.0084 (18)−0.0063 (15)
C110.062 (2)0.037 (2)0.073 (3)−0.0080 (18)−0.009 (2)−0.0133 (17)
C120.064 (2)0.0332 (18)0.068 (2)0.0079 (18)0.006 (2)−0.0025 (16)
C130.048 (2)0.048 (2)0.072 (2)0.0140 (17)0.000 (2)0.0042 (18)
C140.0406 (19)0.0438 (19)0.059 (2)0.0001 (15)−0.0070 (17)−0.0045 (16)
C150.0456 (19)0.0395 (16)0.0415 (18)−0.0051 (16)0.0004 (15)−0.0052 (14)
C160.051 (2)0.058 (2)0.052 (2)0.0088 (18)−0.0033 (19)−0.0058 (18)
C170.066 (3)0.085 (3)0.066 (3)0.009 (2)0.015 (2)−0.018 (2)
C180.082 (3)0.095 (3)0.045 (2)−0.008 (3)0.015 (2)−0.002 (2)
C190.084 (3)0.081 (3)0.054 (2)0.003 (3)−0.001 (2)0.014 (2)
C200.060 (2)0.056 (2)0.051 (2)0.0035 (18)0.0035 (19)0.0005 (17)

Geometric parameters (Å, °)

N1—C11.371 (4)C10—C111.387 (5)
N1—C31.387 (4)C10—H100.930
N1—C81.454 (4)C11—C121.365 (5)
N2—C11.311 (4)C11—H110.930
N2—C21.391 (4)C12—C131.368 (5)
C1—C151.470 (4)C12—H120.930
C2—C71.387 (4)C13—C141.382 (4)
C2—C31.394 (4)C13—H130.930
C3—C41.381 (4)C14—H140.930
C4—C51.373 (5)C15—C201.388 (4)
C4—H40.930C15—C161.389 (4)
C5—C61.388 (5)C16—C171.375 (5)
C5—H50.930C16—H160.930
C6—C71.363 (5)C17—C181.369 (6)
C6—H60.930C17—H170.930
C7—H70.930C18—C191.360 (6)
C8—C91.513 (4)C18—H180.930
C8—H8A0.970C19—C201.373 (5)
C8—H8B0.970C19—H190.930
C9—C101.374 (4)C20—H200.930
C9—C141.387 (4)
C1—N1—C3106.1 (2)C9—C10—C11120.8 (3)
C1—N1—C8130.1 (3)C9—C10—H10119.6
C3—N1—C8123.6 (3)C11—C10—H10119.6
C1—N2—C2105.4 (3)C12—C11—C10120.4 (3)
N2—C1—N1113.1 (3)C12—C11—H11119.8
N2—C1—C15122.2 (3)C10—C11—H11119.8
N1—C1—C15124.7 (3)C11—C12—C13119.6 (3)
C7—C2—C3119.8 (3)C11—C12—H12120.2
C7—C2—N2130.6 (3)C13—C12—H12120.2
C3—C2—N2109.5 (3)C12—C13—C14120.3 (3)
C4—C3—N1131.4 (3)C12—C13—H13119.9
C4—C3—C2122.7 (3)C14—C13—H13119.9
N1—C3—C2105.9 (3)C13—C14—C9120.8 (3)
C5—C4—C3116.2 (4)C13—C14—H14119.6
C5—C4—H4121.9C9—C14—H14119.6
C3—C4—H4121.9C20—C15—C16117.4 (3)
C4—C5—C6121.7 (4)C20—C15—C1124.3 (3)
C4—C5—H5119.2C16—C15—C1118.2 (3)
C6—C5—H5119.2C17—C16—C15121.4 (3)
C7—C6—C5121.9 (4)C17—C16—H16119.3
C7—C6—H6119.0C15—C16—H16119.3
C5—C6—H6119.0C18—C17—C16120.0 (4)
C6—C7—C2117.6 (4)C18—C17—H17120.0
C6—C7—H7121.2C16—C17—H17120.0
C2—C7—H7121.2C19—C18—C17119.4 (4)
N1—C8—C9113.4 (2)C19—C18—H18120.3
N1—C8—H8A108.9C17—C18—H18120.3
C9—C8—H8A108.9C18—C19—C20121.2 (4)
N1—C8—H8B108.9C18—C19—H19119.4
C9—C8—H8B108.9C20—C19—H19119.4
H8A—C8—H8B107.7C19—C20—C15120.5 (3)
C10—C9—C14118.1 (3)C19—C20—H20119.7
C10—C9—C8123.2 (3)C15—C20—H20119.7
C14—C9—C8118.8 (3)
C2—N2—C1—N10.9 (3)C3—N1—C8—C983.9 (3)
C2—N2—C1—C15−178.4 (3)N1—C8—C9—C1012.9 (4)
C3—N1—C1—N2−0.6 (3)N1—C8—C9—C14−167.4 (3)
C8—N1—C1—N2−175.6 (3)C14—C9—C10—C110.6 (5)
C3—N1—C1—C15178.6 (3)C8—C9—C10—C11−179.7 (3)
C8—N1—C1—C153.6 (5)C9—C10—C11—C12−0.6 (6)
C1—N2—C2—C7175.9 (3)C10—C11—C12—C130.3 (6)
C1—N2—C2—C3−0.8 (3)C11—C12—C13—C14−0.1 (6)
C1—N1—C3—C4−177.9 (3)C12—C13—C14—C90.1 (5)
C8—N1—C3—C4−2.4 (5)C10—C9—C14—C13−0.3 (5)
C1—N1—C3—C20.0 (3)C8—C9—C14—C13180.0 (3)
C8—N1—C3—C2175.5 (2)N2—C1—C15—C20−149.6 (3)
C7—C2—C3—C41.6 (4)N1—C1—C15—C2031.2 (5)
N2—C2—C3—C4178.6 (3)N2—C1—C15—C1628.0 (4)
C7—C2—C3—N1−176.6 (3)N1—C1—C15—C16−151.2 (3)
N2—C2—C3—N10.5 (3)C20—C15—C16—C17−2.1 (5)
N1—C3—C4—C5176.1 (3)C1—C15—C16—C17−179.9 (3)
C2—C3—C4—C5−1.5 (5)C15—C16—C17—C180.7 (6)
C3—C4—C5—C60.8 (5)C16—C17—C18—C191.2 (7)
C4—C5—C6—C7−0.1 (6)C17—C18—C19—C20−1.8 (6)
C5—C6—C7—C20.1 (5)C18—C19—C20—C150.4 (6)
C3—C2—C7—C6−0.8 (5)C16—C15—C20—C191.5 (5)
N2—C2—C7—C6−177.2 (3)C1—C15—C20—C19179.2 (3)
C1—N1—C8—C9−101.8 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2334).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J.33, 232–243.
  • Yang, S.-P., Wang, D.-Q., Han, L.-J. & Xia, H.-T. (2007). Acta Cryst. E63, o3758.
  • Zarrinmayeh, H., Nunes, A. M., Ornstein, P. L., Zimmerman, D. A., Gackenheimer, S. L., Bruns, R. F., Hipskind, P. A., Britton, T. C., Cantrell, B. E. & Gehlert, D. R. J. (1998). Med. Chem.41, 2709–2719. [PubMed]

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