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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 [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.100
Data-to-parameter ratio = 14.4
Details
Open access

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

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[Tamm, I. & Sehgal, P. B. (1978). Adv. Virus Res. 22, 187-258.]); Porcari et al. (1998[Porcari, A. R., Devivar, R. V., Kucera, L. S., Drach, J. C. & Townsend, L. B. (1998). J. Med. Chem. 41, 1252-1262.]); Migawa et al. (1998[Migawa, M. T., Girardet, J. L., Walker, J. A., Koszalka, G. W., Chamberlain, S. D., Drach, J. C. & Townsend, L. B. (1998). J. Med. Chem. 41, 1242-1251.]). For their other biological activity, see: Spasov et al. (1999[Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232-243.]); Nakano et al. (2000[Nakano, H., Inoue, T., Kawasaki, N., Miyataka, H., Matsumoto, H., Taguchi, T., Inagaki, N., Nagai, H. & Satoh, T. (2000). Bioorg. Med. Chem. 8, 373-380.]); Zhao et al. (2000[Zhao, Z. S., Arnaiz, D. O., Griedel, B., Sakata, S., Dallas, J. L., Whitlow, M., Trinh, L., Post, J., Liang, A., Morrissey, M. M. & Shaw, K. J. (2000). Bioorg. Med. Chem. Lett. 10, 963-966.]); White et al. (2000[White, A. W., Almassy, R., Calvert, A. H., Curtin, N. J., Griffin, R. J., Hostomsky, Z., Maegley, K., Newell, D. R., Srinivasan, S. & Golding, B. T. (2000). J. Med. Chem. 43, 4084-4097.]); Xiangming et al. (2007[Xiangming, H., Huiqiang, M. & Yulu, W. (2007). ARKIVOC, pp. 150-154.]). For related structures, see: Kia et al. (2009[Kia, R., Fun, H.-K. & Kargar, H. (2009). Acta Cryst. E65, o660-o661.]); Zhou et al. (2009[Zhou, J.-C., Zhang, Z.-Y., Li, N.-X. & Zhang, C.-M. (2009). Acta Cryst. E65, o3019.]). For synthetic details, see: Lutfor et al. (2008[Lutfor, M. R., Jahimin, A., Sandeep, K. & Tschierske, C. (2008). Liq. Cryst. 35, 1263-1270.]). For standard 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.]).

[Scheme 1]

Experimental

Crystal data
  • C26H24N2O2

  • Mr = 396.49

  • Monoclinic, P 21 /n

  • a = 12.5455 (1) Å

  • b = 10.1989 (1) Å

  • c = 15.9340 (2) Å

  • [beta] = 99.5027 (11)°

  • V = 2010.78 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 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[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.80, Tmax = 0.95

  • 38976 measured reflections

  • 3908 independent reflections

  • 3563 reflections with I > 2.0[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.100

  • S = 0.99

  • 3891 reflections

  • 271 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]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-H...A D-H H...A D...A D-H...A
C12-H121...Cg4i 0.97 2.62 3.5064 (13) 153
C23-H231...Cg3ii 0.96 2.73 3.6859 (15) 175
C30-H301...Cg2iii 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[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: 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: 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

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
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.
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  [ISI] [CrossRef] [details]
Kia, R., Fun, H.-K. & Kargar, H. (2009). Acta Cryst. E65, o660-o661.  [CSD] [CrossRef] [details]
Lutfor, M. R., Jahimin, A., Sandeep, K. & Tschierske, C. (2008). Liq. Cryst. 35, 1263-1270.
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]
Migawa, M. T., Girardet, J. L., Walker, J. A., Koszalka, G. W., Chamberlain, S. D., Drach, J. C. & Townsend, L. B. (1998). J. Med. Chem. 41, 1242-1251.  [ISI] [CrossRef] [ChemPort] [PubMed]
Nakano, H., Inoue, T., Kawasaki, N., Miyataka, H., Matsumoto, H., Taguchi, T., Inagaki, N., Nagai, H. & Satoh, T. (2000). Bioorg. Med. Chem. 8, 373-380.  [CrossRef] [PubMed] [ChemPort]
Porcari, A. R., Devivar, R. V., Kucera, L. S., Drach, J. C. & Townsend, L. B. (1998). J. Med. Chem. 41, 1252-1262.  [ISI] [CrossRef] [ChemPort] [PubMed]
Spasov, A. A., Yozhitsa, I. N., Bugaeva, L. I. & Anisimova, V. A. (1999). Pharm. Chem. J. 33, 232-243.  [CrossRef] [ChemPort]
Tamm, I. & Sehgal, P. B. (1978). Adv. Virus Res. 22, 187-258.  [CrossRef] [ChemPort] [PubMed]
White, A. W., Almassy, R., Calvert, A. H., Curtin, N. J., Griffin, R. J., Hostomsky, Z., Maegley, K., Newell, D. R., Srinivasan, S. & Golding, B. T. (2000). J. Med. Chem. 43, 4084-4097.  [ISI] [CrossRef] [PubMed] [ChemPort]
Xiangming, H., Huiqiang, M. & Yulu, W. (2007). ARKIVOC, pp. 150-154.
Zhao, Z. S., Arnaiz, D. O., Griedel, B., Sakata, S., Dallas, J. L., Whitlow, M., Trinh, L., Post, J., Liang, A., Morrissey, M. M. & Shaw, K. J. (2000). Bioorg. Med. Chem. Lett. 10, 963-966.  [CrossRef] [PubMed] [ChemPort]
Zhou, J.-C., Zhang, Z.-Y., Li, N.-X. & Zhang, C.-M. (2009). Acta Cryst. E65, o3019.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3311-o3312   [ doi:10.1107/S160053681204559X ]

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