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

Simpson, J.; Mohamed, S.K.; Marzouk, A.A.; Talybov, A.H.; Abdelhamid, A.A.

doi:10.1107/S1600536812049100

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 (C-C) = 0.002 Å
R = 0.048
wR = 0.132
Data-to-parameter ratio = 18.2
Details

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

Jim Simpson,^a Shaaban K. Mohamed,^b,^c ^* Adel A. Marzouk,^d Avtandil H. Talybov ^e and Antar A. Abdelhamid ^f

^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-HO 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); Radziszewski (1877); Maeda & Hayashi (1969, 1970). For the bioactivity of imidazoles, see: Antolini et al. (1999); Eyers et al. (1998); Laszlo et al. (1999); Newman et al. (2000); Veisi et al. (2012); Wang et al. (2002). For related structures, see, for example: Yanover & Kaftory (2009a,b); Kison & Opatz (2009); Zhao et al. (2012). For representative bond lengths, see: Allen et al. (1987) and for hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₇H₂₈N₂O
M_r = 396.51
Triclinic, $[P \overline 1]$
a = 9.7214 (19) Å
b = 10.739 (1) Å
c = 11.7367 (10) Å
= 114.069 (4)°
= 99.021 (6)°
= 95.425 (6)°
V = 1087.7 (3) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.619, T_max = 0.746
15574 measured reflections
4968 independent reflections
3542 reflections with I > 2(I)
R_int = 0.043

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.132
S = 1.06
4968 reflections
273 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H15O119ⁱ	0.95	2.61	3.4393 (19)	146
Symmetry code: (i) -x+2, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 and SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and TITAN2000 (Hunter & Simpson, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and TITAN2000; molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

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

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organic compounds