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Volume 69 
Part 8 
Page o1330  
August 2013  

Received 19 June 2013
Accepted 23 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.088
Data-to-parameter ratio = 18.3
Details
Open access

1-(2,6-Diisopropylphenyl)-1H-benzimidazole

aPharmaceutical Department of The First Affiliated Hospital of Guangdong Pharmaceutical University, Clinical Pharmacy Department of Guangdong Pharmaceutical University, Guangzhou 510080, People's Republic of China
Correspondence e-mail: puma_0003@163.com

In the title compound, C19H22N2, both the benzimidazole unit and the 2,6-diisopropylphenyl group are essentially planar [maximum deviations from the least-squares planes of 0.005 (1) and 0.009 (1) Å, respectively]. The dihedral angle between the two planes is 79.6 (7)°. In the crystal, molecules are linked into chains along the a-axis direction by weak C-H...N interactions. The crystal structure also features C-H...[pi] interactions, which link the chains into a three-dimensional network.

Related literature

For the properties of related compounds, see: Shi et al. (2013[Shi, H., Wu, T., Jiang, P., Jin, X. & Zhu, H. (2013). Asian J. Chem. 25, 4481-4486.]); Cross et al. (1995[Cross, E. M., White, K. M., Moshrefzadeh, R. S. & Francis, C. V. (1995). Macromolecules, 28, 2526-2532.]); Akpinar et al. (2010[Akpinar, H., Balan, A., Baran, D., Unver, E. K. & Toppare, L. (2010). Polymer, 51, 6123-6131.]); Wang et al. (2007[Wang, H., Li, M., Shao, M. & He, X. (2007). Polyhedron, 26, 5171-5176.]); Mason et al. (1999[Mason, J. S., Morize, I., Menard, P. R., Cheney, D. L., Hume, C. & Labaudiniere, R. F. (1999). J. Med. Chem. 42, 3251-3264.]). For bond lengths and angles in related structures, see: Jayamoorthy et al. (2013[Jayamoorthy, K., Mohandas, T., Sakthivel, P. & Jayabharathi, J. (2013). Acta Cryst. E69, o244.]); Fathima et al. (2013[Fathima, N., Krishnamurthy, M. S. & Begum, N. S. (2013). Acta Cryst. E69, o264.]); Geiger & Nellist (2013[Geiger, D. K. & Nellist, M. R. (2013). Acta Cryst. E69, o807.]).

[Scheme 1]

Experimental

Crystal data
  • C19H22N2

  • Mr = 278.39

  • Orthorhombic, P 21 21 21

  • a = 6.6471 (8) Å

  • b = 14.1216 (18) Å

  • c = 17.285 (2) Å

  • V = 1622.5 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 173 K

  • 0.44 × 0.42 × 0.28 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.971, Tmax = 0.982

  • 9716 measured reflections

  • 3551 independent reflections

  • 3133 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.088

  • S = 1.08

  • 3551 reflections

  • 194 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2-C7 and C8/C9/C13-C16 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C6-H6...N1i 0.95 2.47 3.4040 (18) 168
C14-H14...Cg3ii 0.95 2.68 3.5908 (16) 150
C18-H18B...Cg2iii 0.98 2.79 3.5314 (17) 125
Symmetry codes: (i) x-1, y, z; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iii) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2510 ).


Acknowledgements

We acknowledge the Foundation for Distinguished Young Talents in Higher Education of Guangdong (No. LYM10091) for financial support.

References

Akpinar, H., Balan, A., Baran, D., Unver, E. K. & Toppare, L. (2010). Polymer, 51, 6123-6131.  [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cross, E. M., White, K. M., Moshrefzadeh, R. S. & Francis, C. V. (1995). Macromolecules, 28, 2526-2532.  [CrossRef] [ChemPort] [Web of Science]
Fathima, N., Krishnamurthy, M. S. & Begum, N. S. (2013). Acta Cryst. E69, o264.  [CrossRef] [IUCr Journals]
Geiger, D. K. & Nellist, M. R. (2013). Acta Cryst. E69, o807.  [CSD] [CrossRef] [IUCr Journals]
Jayamoorthy, K., Mohandas, T., Sakthivel, P. & Jayabharathi, J. (2013). Acta Cryst. E69, o244.  [CrossRef] [IUCr Journals]
Mason, J. S., Morize, I., Menard, P. R., Cheney, D. L., Hume, C. & Labaudiniere, R. F. (1999). J. Med. Chem. 42, 3251-3264.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shi, H., Wu, T., Jiang, P., Jin, X. & Zhu, H. (2013). Asian J. Chem. 25, 4481-4486.  [ChemPort]
Wang, H., Li, M., Shao, M. & He, X. (2007). Polyhedron, 26, 5171-5176.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1330  [ doi:10.1107/S1600536813020473 ]

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