[Journal logo]

Volume 69 
Part 4 
Pages o527-o528  
April 2013  

Received 25 February 2013
Accepted 5 March 2013
Online 9 March 2013

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.004 Å
R = 0.043
wR = 0.118
Data-to-parameter ratio = 13.0
Details
Open access

4-(1-Allyl-4,5-diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,bDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA,cChemistry Department, Faculty of Science, Minia University, El-Minia, Egypt,dChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,eManedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan, and fPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt
Correspondence e-mail: shaabankamel@yahoo.com, akkurt@erciyes.edu.tr

The title compound, C26H25N3, crystallizes with four independent molecules, 1-4, in the asymmetric unit of the triclinic unit cell. The allyl substituents on the imidazole rings adopt similar conformations in all four molecules. The imadazole and the 4-and 5-substituted phenyl rings of two pairs of molecules in the asymmetric unit stack parallel to (110). In contrast, the dimethylaniline systems in these pairs of molecules are almost normal to one another, with dihedral angles of 85.84 (10) and 85.65 (10)° between the benzene rings of the two dimethylaniline fragments of molecules 1 and 2, and 3 and 4, respectively. The crystal structure features an extensive series of C-H...[pi] interactions that link the molecules into undulating rows along the c axis. The crystal studied was a pseudo-merohedral twin with twin law [-100, 0-10, 111] and the BASF parameter refined to 0.513 (3).

Related literature

For the synthesis and bioactivity of related heterocyclic molecules, see: El-Sawy et al. (2012[El-Sawy, A. A., Mohamed, S. K., Eissa, A. M. F., Tantawy, A. H. & Issac, Y. A. (2012). J. Chem. Pharm. Res. 4, 2755-2762.]); Issac et al. (2012[Issac, Y. A., Mohamed, S. K., Eissa, A. M. F., Tantawy, A. H. & El-Sawy, A. A. (2012). J. Chem. Pharm. Res. 4, 2744-2750.]); Mohamed, Abdelhamid et al. (2012[Mohamed, S. K., Abdelhamid, A. A., Maharramov, A. M., Khalilov, A. N., Gurbanov, A. V. & Allahverdiyev, M. A. (2012). J. Chem. Pharm. Res. 4, 955-965.]); Soliman et al. (2012[Soliman, A. M., Mohamed, S. K., Elremaily, M. A. A. & Abdel-Ghany, H. (2012). Eur. J. Med. Chem. 47, 138-142.]). For the synthesis of a similar imidazole derivative, see: Mohamed, Akkurt et al. (2012[Mohamed, S. K., Akkurt, M., Fronczek, F. R., Marzouk, A. A. E. & Abdelhamid, A. A. (2012). Acta Cryst. E68, o2979-o2980.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C26H25N3

  • Mr = 379.49

  • Triclinic, [P \overline 1]

  • a = 9.4259 (7) Å

  • b = 10.2028 (7) Å

  • c = 44.721 (3) Å

  • [alpha] = 94.711 (2)°

  • [beta] = 94.096 (2)°

  • [gamma] = 107.359 (2)°

  • V = 4070.2 (5) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.57 mm-1

  • T = 90 K

  • 0.31 × 0.29 × 0.17 mm

Data collection
  • Bruker Kappa APEXII DUO diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.844, Tmax = 0.910

  • 26145 measured reflections

  • 13651 independent reflections

  • 13253 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.118

  • S = 1.03

  • 13651 reflections

  • 1054 parameters

  • 72 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg8, Cg6, Cg4, Cg10, Cg16, Cg14 and Cg12 are the centroids of the C4-C9, C47-C52, C30-C35, C21-C26, C56-C61, C99-C104, C82-C87 and C73-C78 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C10-H10A...Cg2i 0.98 2.71 3.514 (3) 139
C16-H16...Cg8 0.95 2.47 3.328 (3) 151
C37-H37A...Cg6ii 0.98 2.77 3.600 (2) 142
C42-H42...Cg4iii 0.95 2.49 3.345 (3) 150
C63-H63A...Cg10iv 0.98 2.73 3.595 (2) 147
C68-H68...Cg16 0.95 2.59 3.390 (3) 142
C88-H88C...Cg14v 0.98 2.74 3.509 (3) 136
C94-H94...Cg12iii 0.95 2.48 3.340 (3) 150
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+2, -y+1, -z; (iii) x+1, y+1, z; (iv) -x+1, -y+1, -z+1; (v) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: SJ5302 ).


Acknowledgements

Manchester Metropolitan University, Erciyes University and Louisiana State University are gratefully acknowledged for supporting this study.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Sawy, A. A., Mohamed, S. K., Eissa, A. M. F., Tantawy, A. H. & Issac, Y. A. (2012). J. Chem. Pharm. Res. 4, 2755-2762.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Issac, Y. A., Mohamed, S. K., Eissa, A. M. F., Tantawy, A. H. & El-Sawy, A. A. (2012). J. Chem. Pharm. Res. 4, 2744-2750.  [ChemPort]
Mohamed, S. K., Abdelhamid, A. A., Maharramov, A. M., Khalilov, A. N., Gurbanov, A. V. & Allahverdiyev, M. A. (2012). J. Chem. Pharm. Res. 4, 955-965.  [ChemPort]
Mohamed, S. K., Akkurt, M., Fronczek, F. R., Marzouk, A. A. E. & Abdelhamid, A. A. (2012). Acta Cryst. E68, o2979-o2980.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Soliman, A. M., Mohamed, S. K., Elremaily, M. A. A. & Abdel-Ghany, H. (2012). Eur. J. Med. Chem. 47, 138-142.  [ISI] [CrossRef] [ChemPort] [PubMed]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o527-o528   [ doi:10.1107/S1600536813006326 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.