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Volume 69 
Part 1 
Pages o5-o6  
January 2013  

Received 27 November 2012
Accepted 29 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 93 K
Mean [sigma](C-C) = 0.002 Å
R = 0.048
wR = 0.132
Data-to-parameter ratio = 18.2
Details
Open access

2-(4-Methoxyphenyl)-1-pentyl-4,5-diphenyl-1H-imidazole

aDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand,bChemistry Department, Faculty of Science, Minia University, El-Minia, Egypt,cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,dPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt,eManedaliev Institute of Petrochemical Processes, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan, and fChemistry Department, Faculty of Science, Sohag University, Sohag 82524, Egypt
Correspondence e-mail: shaabankamel@yahoo.com

The title compound, C27H28N2O, is a lophine (2,4,5-triphenyl-1H-imidazole) derivative with an n-pentyl chain on the amine N atom and a 4-methoxy substituent on the benzene ring. The two phenyl and methoxybenzene rings are inclined to the imidazole ring at angles of 25.32 (7), 76.79 (5) and 35.42 (7)°, respectively, while the methoxy substituent lies close to the plane of its benzene ring, with a maximum deviation of 0.126 (3) Å for the methoxy C atom. In the crystal, inversion dimers linked by pairs of C-H...O hydrogen bonds generate R22(22) loops. These dimers are stacked along the a-axis direction.

Related literature

For the non-linear optical and chemiluminescence properties of lophine and its derivatives, see: Santos et al. (2001[Santos, J., Mintz, E. A., Zehnder, O., Bosshard, C., Bu, X. R. & Gunter, P. (2001). Tetrahedron Lett. 42, 805-808.]); Radziszewski (1877[Radziszewski, B. (1877). Chem. Ber. 10, 70-75.]); Maeda & Hayashi (1969[Maeda, K. & Hayashi, T. (1969). Bull. Chem. Soc. Jpn, 42, 3509-3514.], 1970[Maeda, K. & Hayashi, T. (1970). Bull. Chem. Soc. Jpn, 43, 429-438.]). For the bioactivity of imidazoles, see: Antolini et al. (1999[Antolini, M., Bozzoli, A., Ghiron, C., Kennedy, G., Rossi, T. & Ursini, A. (1999). Bioorg. Med. Chem. Lett. 9, 1023-1028.]); Eyers et al. (1998[Eyers, P. A., Craxton, M., Morrice, N. & Cohen, P. (1998). J. Chem. Biol. 5, 321-328.]); Laszlo et al. (1999[Laszlo, De S. E., Hacker, C., Li, B., Kim, D., MacCoss, M., Mantlo, N., Pivnichny, J. V., Colwell, L., Koch, G. E., Cascieri, M. A. & Hagmann, W. K. (1999). Bioorg. Med. Chem. Lett. 9, 641-646.]); Newman et al. (2000[Newman, M. J., Rodarte, J. C., Benbatoul, K. D., Romano, S. J., Zhang, C., Krane, S., Moran, E. J., Uyeda, R. T., Dixon, R., Guns, E. S. & Mayer, L. D. V. (2000). Cancer Res. 60, 2964-2972.]); Veisi et al. (2012[Veisi, H., Khazaei, A., Heshmati, L. & Hemmati, S. (2012). Bull. Korean Chem. Soc. 33, 1231-1234.]); Wang et al. (2002[Wang, L., Woods, K. W., Li, Q., Barr, K. J., McCroskey, R. W., Hannick, S. M., Gherke, L., Credo, R. B., Hui, Y.-H., Marsh, K., Warner, R., Lee, J. Y., Zielinsky-Mozng, N., Frost, D., Rosenberg, S. H. & Sham, H. L. (2002). J. Med. Chem. 45, 1697-1711.]). For related structures, see, for example: Yanover & Kaftory (2009a[Yanover, D. & Kaftory, M. (2009a). Acta Cryst. E65, o711.],b[Yanover, D. & Kaftory, M. (2009b). Acta Cryst. C65, o365-o370.]); Kison & Opatz (2009[Kison, C. & Opatz, T. (2009). Chem. Eur. J. 15, 843-845.]); Zhao et al. (2012[Zhao, B., Li, Z., Fan, M., Song, B. & Deng, Q. (2012). Acta Cryst. E68, o542.]). For representative bond lengths, 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.]) and for hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C27H28N2O

  • Mr = 396.51

  • Triclinic, [P \overline 1]

  • a = 9.7214 (19) Å

  • b = 10.739 (1) Å

  • c = 11.7367 (10) Å

  • [alpha] = 114.069 (4)°

  • [beta] = 99.021 (6)°

  • [gamma] = 95.425 (6)°

  • V = 1087.7 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 93 K

  • 0.47 × 0.18 × 0.08 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.619, Tmax = 0.746

  • 15574 measured reflections

  • 4968 independent reflections

  • 3542 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.132

  • S = 1.06

  • 4968 reflections

  • 273 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15...O119i 0.95 2.61 3.4393 (19) 146
Symmetry code: (i) -x+2, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT (Bruker, 2011[Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and TITAN2000 (Hunter & Simpson, 1999[Hunter, K. A. & Simpson, J. (1999). TITAN2000. University of Otago, New Zealand.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and TITAN2000; molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6874 ).


Acknowledgements

We thank the University of Otago for purchase of the diffractometer.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.  [ISI] [CrossRef] [ChemPort] [details]
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.
Antolini, M., Bozzoli, A., Ghiron, C., Kennedy, G., Rossi, T. & Ursini, A. (1999). Bioorg. Med. Chem. Lett. 9, 1023-1028.  [CrossRef] [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2011). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Eyers, P. A., Craxton, M., Morrice, N. & Cohen, P. (1998). J. Chem. Biol. 5, 321-328.  [ChemPort]
Hunter, K. A. & Simpson, J. (1999). TITAN2000. University of Otago, New Zealand.
Kison, C. & Opatz, T. (2009). Chem. Eur. J. 15, 843-845.  [CSD] [CrossRef] [PubMed] [ChemPort]
Laszlo, De S. E., Hacker, C., Li, B., Kim, D., MacCoss, M., Mantlo, N., Pivnichny, J. V., Colwell, L., Koch, G. E., Cascieri, M. A. & Hagmann, W. K. (1999). Bioorg. Med. Chem. Lett. 9, 641-646.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Maeda, K. & Hayashi, T. (1969). Bull. Chem. Soc. Jpn, 42, 3509-3514.  [CrossRef] [ChemPort] [ISI]
Maeda, K. & Hayashi, T. (1970). Bull. Chem. Soc. Jpn, 43, 429-438.  [CrossRef] [ChemPort] [ISI]
Newman, M. J., Rodarte, J. C., Benbatoul, K. D., Romano, S. J., Zhang, C., Krane, S., Moran, E. J., Uyeda, R. T., Dixon, R., Guns, E. S. & Mayer, L. D. V. (2000). Cancer Res. 60, 2964-2972.  [ISI] [PubMed] [ChemPort]
Radziszewski, B. (1877). Chem. Ber. 10, 70-75.
Santos, J., Mintz, E. A., Zehnder, O., Bosshard, C., Bu, X. R. & Gunter, P. (2001). Tetrahedron Lett. 42, 805-808.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Veisi, H., Khazaei, A., Heshmati, L. & Hemmati, S. (2012). Bull. Korean Chem. Soc. 33, 1231-1234.  [ChemPort]
Wang, L., Woods, K. W., Li, Q., Barr, K. J., McCroskey, R. W., Hannick, S. M., Gherke, L., Credo, R. B., Hui, Y.-H., Marsh, K., Warner, R., Lee, J. Y., Zielinsky-Mozng, N., Frost, D., Rosenberg, S. H. & Sham, H. L. (2002). J. Med. Chem. 45, 1697-1711.  [ISI] [CrossRef] [PubMed] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Yanover, D. & Kaftory, M. (2009a). Acta Cryst. E65, o711.  [CSD] [CrossRef] [details]
Yanover, D. & Kaftory, M. (2009b). Acta Cryst. C65, o365-o370.  [CSD] [CrossRef] [details]
Zhao, B., Li, Z., Fan, M., Song, B. & Deng, Q. (2012). Acta Cryst. E68, o542.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o5-o6   [ doi:10.1107/S1600536812049100 ]

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