1-[4-(Prop-2-en-1-yl­oxy)benz­yl]-2-[4-(prop-2-en-1-yl­oxy)phen­yl]-1H-benzimidazole

Rahman, M.L.; Kwong, H.C.; Mohdusoff, M.; Hegde, G.; Mohamed Tahir, M.I.

doi:10.1107/S160053681204559X

Volume 68
Part 12
Pages o3311-o3312
December 2012

Received 1 October 2012
Accepted 5 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.038
wR = 0.100
Data-to-parameter ratio = 14.4
Details

1-[4-(Prop-2-en-1-yloxy)benzyl]-2-[4-(prop-2-en-1-yloxy)phenyl]-1H-benzimidazole

Md. Lutfor Rahman,^a ^* Huey Chong Kwong,^b Mashitah Mohd. Yusoff,^a Gurumurthy Hegde ^a and Mohamed Ibrahim Mohamed Tahir ^b

^aUniversity Malaysia Pahang, Faculty of Industrial Sciences and Technology, 26300 Gambang, Kuantan, Pahang, Malaysia, and ^bDepartment Chemistry, Faculty Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia
Correspondence e-mail: lutfor73@gmail.com

In the title compound, C₂₆H₂₄N₂O₂, the benzimidazole ring system is almost planar [maximum displacement = 0.025 (1) Å] and makes dihedral angles of 80.48 (5) and 41.57 (5)° with the benzene rings, which are inclined to one another by 65.33 (6)°. In the crystal, molecules are linked via C-H [pi] and weak [pi] - [pi] interactions [centroid-centroid distance = 3.8070 (7) Å and interplanar distance = 3.6160 (5) Å].

Related literature

For the activity of benzimidazole derivatives against viruses, see: Tamm & Sehgal (1978); Porcari et al. (1998); Migawa et al. (1998). For their other biological activity, see: Spasov et al. (1999); Nakano et al. (2000); Zhao et al. (2000); White et al. (2000); Xiangming et al. (2007). For related structures, see: Kia et al. (2009); Zhou et al. (2009). For synthetic details, see: Lutfor et al. (2008). For standard bond lengths, see Allen et al. (1987).

Experimental

Crystal data

C₂₆H₂₄N₂O₂
M_r = 396.49
Monoclinic, P 2₁ /n
a = 12.5455 (1) Å
b = 10.1989 (1) Å
c = 15.9340 (2) Å
= 99.5027 (11)°
V = 2010.78 (4) Å³
Z = 4
Cu K radiation
= 0.66 mm^-1
T = 100 K
0.35 × 0.23 × 0.08 mm

Data collection

Agilent Technologies Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.80, T_max = 0.95
38976 measured reflections
3908 independent reflections
3563 reflections with I > 2.0(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.100
S = 0.99
3891 reflections
271 parameters
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2-C5/C26/C27 ring; Cg3 is the centroid of the C10-C15 ring and Cg4 is the centroid of the C16-C19/C24/25 ring.

D-HA	D-H	HA	DA	D-HA
C12-H121Cg4ⁱ	0.97	2.62	3.5064 (13)	153
C23-H231Cg3ⁱⁱ	0.96	2.73	3.6859 (15)	175
C30-H301Cg2ⁱⁱⁱ	0.95	2.72	3.6202 (14)	159
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x, -y+1, -z+1; (iii) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: CRYSTALS.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2508 ).

Acknowledgements

This research was supported by a UMP research grant (No. RDU100338).

References

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organic compounds