organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aDongchang College, Liaocheng University, Liaocheng 250059, People's Republic of China
*Correspondence e-mail: konglingqian08@163.com

(Received 7 December 2008; accepted 10 January 2009; online 14 January 2009)

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[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.]); Spasov et al. (1999[Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232-243.]). For a related structure, see: Yang et al. (2007[Yang, S.-P., Wang, D.-Q., Han, L.-J. & Xia, H.-T. (2007). Acta Cryst. E63, o3758.]).

[Scheme 1]

Experimental

Crystal data
  • C20H16N2

  • Mr = 284.35

  • Orthorhombic, P 21 21 21

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.956, Tmax = 0.967

  • 6729 measured reflections

  • 1631 independent reflections

  • 1221 reflections with I > 2σ(I)

  • Rint = 0.073

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 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[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] Fig. 1. Molecular structure showing 30% probability displacement ellipsoids for non-H atoms.
1-Benzyl-2-phenyl-1H-benzimidazole top
Crystal data top
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 top
Bruker SMART CCD
diffractometer
1631 independent reflections
Radiation source: fine-focus sealed tube1221 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
ϕ and ω scansθmax = 25.1°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.956, Tmax = 0.967k = 97
6729 measured reflectionsl = 2636
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.14 w = 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
Crystal data top
C20H16N2V = 1547.0 (10) Å3
Mr = 284.35Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.338 (3) ŵ = 0.07 mm1
b = 8.085 (3) ÅT = 298 K
c = 30.190 (12) Å0.63 × 0.55 × 0.47 mm
Data collection top
Bruker SMART CCD
diffractometer
1631 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1221 reflections with I > 2σ(I)
Tmin = 0.956, Tmax = 0.967Rint = 0.073
6729 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.14Δρmax = 0.14 e Å3
1631 reflectionsΔρmin = 0.16 e Å3
199 parameters
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
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)
H40.00510.04220.21100.065*
C50.1920 (7)0.1639 (5)0.25254 (13)0.0678 (11)
H50.10020.16670.27660.081*
C60.3909 (7)0.2340 (5)0.25674 (13)0.0683 (12)
H60.42880.28240.28350.082*
C70.5324 (7)0.2341 (4)0.22272 (12)0.0588 (10)
H70.66510.28160.22590.071*
C80.0616 (5)0.0304 (4)0.11706 (11)0.0422 (8)
H8A0.05870.02900.12900.051*
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*
C120.0329 (6)0.5478 (4)0.14239 (12)0.0551 (9)
H120.05500.65970.14770.066*
C130.1927 (6)0.4519 (4)0.12605 (12)0.0559 (10)
H130.32390.49880.12030.067*
C140.1601 (5)0.2856 (4)0.11803 (11)0.0479 (9)
H140.26980.22150.10690.057*
C150.4924 (5)0.0445 (4)0.06922 (10)0.0422 (8)
C160.6356 (5)0.1483 (4)0.04824 (12)0.0538 (9)
H160.69570.23510.06400.065*
C170.6904 (6)0.1255 (6)0.00461 (13)0.0721 (12)
H170.78540.19720.00890.087*
C180.6052 (7)0.0028 (5)0.01897 (14)0.0737 (13)
H180.63980.01740.04870.088*
C190.4695 (7)0.1087 (5)0.00140 (12)0.0730 (12)
H190.41470.19760.01440.088*
C200.4119 (6)0.0867 (4)0.04484 (11)0.0555 (9)
H200.31830.16030.05800.067*
Atomic displacement parameters (Å2) top
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, º) top
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—C15178.4 (3)N1—C8—C9—C1012.9 (4)
C3—N1—C1—N20.6 (3)N1—C8—C9—C14167.4 (3)
C8—N1—C1—N2175.6 (3)C14—C9—C10—C110.6 (5)
C3—N1—C1—C15178.6 (3)C8—C9—C10—C11179.7 (3)
C8—N1—C1—C153.6 (5)C9—C10—C11—C120.6 (6)
C1—N2—C2—C7175.9 (3)C10—C11—C12—C130.3 (6)
C1—N2—C2—C30.8 (3)C11—C12—C13—C140.1 (6)
C1—N1—C3—C4177.9 (3)C12—C13—C14—C90.1 (5)
C8—N1—C3—C42.4 (5)C10—C9—C14—C130.3 (5)
C1—N1—C3—C20.0 (3)C8—C9—C14—C13180.0 (3)
C8—N1—C3—C2175.5 (2)N2—C1—C15—C20149.6 (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—N1176.6 (3)N1—C1—C15—C16151.2 (3)
N2—C2—C3—N10.5 (3)C20—C15—C16—C172.1 (5)
N1—C3—C4—C5176.1 (3)C1—C15—C16—C17179.9 (3)
C2—C3—C4—C51.5 (5)C15—C16—C17—C180.7 (6)
C3—C4—C5—C60.8 (5)C16—C17—C18—C191.2 (7)
C4—C5—C6—C70.1 (6)C17—C18—C19—C201.8 (6)
C5—C6—C7—C20.1 (5)C18—C19—C20—C150.4 (6)
C3—C2—C7—C60.8 (5)C16—C15—C20—C191.5 (5)
N2—C2—C7—C6177.2 (3)C1—C15—C20—C19179.2 (3)
C1—N1—C8—C9101.8 (4)

Experimental details

Crystal data
Chemical formulaC20H16N2
Mr284.35
Crystal system, space groupOrthorhombic, P212121
Temperature (K)298
a, b, c (Å)6.338 (3), 8.085 (3), 30.190 (12)
V3)1547.0 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.63 × 0.55 × 0.47
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.956, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections
6729, 1631, 1221
Rint0.073
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.115, 1.14
No. of reflections1631
No. of parameters199
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.14, 0.16

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

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

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232–243.  CrossRef CAS Google Scholar
First citationYang, S.-P., Wang, D.-Q., Han, L.-J. & Xia, H.-T. (2007). Acta Cryst. E63, o3758.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationZarrinmayeh, 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.  Web of Science CSD CrossRef CAS Google Scholar

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