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Volume 69 
Part 6 
Page o886  
June 2013  

Received 26 April 2013
Accepted 7 May 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.050
wR = 0.125
Data-to-parameter ratio = 21.8
Details
Open access

Ethyl 2-[4-(dimethylamino)phenyl]-1-phenyl-1H-benzimidazole-5-carboxylate

aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: arazaki@usm.my

In the title compound, C24H23N3O2, the benzimidazole ring system makes dihedral angles of 7.28 (5) and 67.17 (5)°, respectively, with the planes of the benzene and phenyl rings, which in turn make a dihedral angle of 69.77 (6)°. In the crystal, molecules are connected by C-H...N and C-H...O interactions, forming a layer parallel to the bc plane. A [pi]-[pi] interaction, with a centroid-centroid distance of 3.656 (1) Å, is observed in the layer.

Related literature

For applications of benzimidazole compounds, see: Rao et al. (2002[Rao, A., Chimirri, A., Clercq, E. D., Monforte, A. M., Monforte, P., Pannecouque, C. & Zappala, M. (2002). Il Farmaco, 57, 819-823.]); Thakurdesai et al. (2007[Thakurdesai, P. A., Wadodkar, S. G. & Chopade, C. T. (2007). Pharmacology Online, 1, 314-329.]); McKellar & Scott (1990[McKellar, Q. A. & Scott, E. W. (1990). J. Vet. Pharmacol. Ther. 13, 223-247.]). For a related structure, see: Yoon et al. (2012[Yoon, Y. K., Ali, M. A., Choon, T. S., Asik, S. I. J. & Razak, I. A. (2012). Acta Cryst. E68, o59.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C24H23N3O2

  • Mr = 385.45

  • Triclinic, [P \overline 1]

  • a = 8.7196 (1) Å

  • b = 10.4133 (2) Å

  • c = 11.3658 (2) Å

  • [alpha] = 79.312 (1)°

  • [beta] = 74.393 (1)°

  • [gamma] = 89.781 (1)°

  • V = 975.56 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.36 × 0.25 × 0.25 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.970, Tmax = 0.980

  • 21016 measured reflections

  • 5777 independent reflections

  • 4602 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.125

  • S = 1.03

  • 5777 reflections

  • 265 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15A...N2i 0.95 2.57 3.4868 (16) 164
C18-H18A...O2ii 0.95 2.50 3.2217 (17) 133
C19-H19A...O2iii 0.95 2.38 3.3209 (16) 170
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x, y, z+1; (iii) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5269 ).


Acknowledgements

The authors would like to express their gratitude to Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine and Department of Pharmacology, School of Pharmaceutical Sciences, Universiti Sains Malaysia. This work was funded through Research Grant No. RUC (1001/PSK/8620012) and HiCoE Research Grant No (311/CIPPM/4401005). IAR also thanks USM for the Short Term Grant, No. 304/PFIZIK/6312078.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
McKellar, Q. A. & Scott, E. W. (1990). J. Vet. Pharmacol. Ther. 13, 223-247.  [CrossRef] [ChemPort] [PubMed] [ISI]
Rao, A., Chimirri, A., Clercq, E. D., Monforte, A. M., Monforte, P., Pannecouque, C. & Zappala, M. (2002). Il Farmaco, 57, 819-823.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Thakurdesai, P. A., Wadodkar, S. G. & Chopade, C. T. (2007). Pharmacology Online, 1, 314-329.
Yoon, Y. K., Ali, M. A., Choon, T. S., Asik, S. I. J. & Razak, I. A. (2012). Acta Cryst. E68, o59.  [CrossRef] [details]


Acta Cryst (2013). E69, o886  [ doi:10.1107/S1600536813012440 ]

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