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Volume 69 
Part 9 
Page o1379  
September 2013  

Received 29 June 2013
Accepted 28 July 2013
Online 3 August 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.004 Å
R = 0.033
wR = 0.085
Data-to-parameter ratio = 14.1
Details
Open access

2-[2-(5-Bromothiophen-2-yl)-4,5-diphenyl-1H-imidazol-1-yl]-3-phenylpropan-1-ol

aSchool of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001, People's Republic of China
Correspondence e-mail: henangongda@yahoo.com

In the title compound, C28H23BrN2OS, the dihedral angles formed by the imidazole ring with the 5-bromothiophenyl and phenyl rings are 76.90 (8), 34.02 (10) and 80.93 (11)°, respectively. The chiral centre maintains the S configuration of the L-phenylalaninol starting material. In the crystal, molecules are linked by O-H...N hydrogen bonds, forming chains running parallel to the a-axis direction.

Related literature

For the synthesis of imidazole rings, see: Jiang et al. (2009[Jiang, B., Wang, X., Shi, F., Tu, S., Ai, T., Ballew, A. & Li, G. (2009). J. Org. Chem. 74, 9486-9489.]); Wu et al. (2010[Wu, X., Jiang, R., Xu, X., Su, X., Lu, W. & Ji, S. (2010). J. Comb. Chem. 12, 829-835.]); Eseola et al. (2010[Eseola, A. O., Zhang, M., Xiang, J., Zuo, W., Li, Y., Woods, J. A. O. & Sun, W. (2010). Inorg. Chim. Acta, 363, 1970-1978.]). For related compounds synthesized by our group, see: Mao et al. (2010[Mao, P., Cai, Y., Xiao, Y., Yang, L., Xue, Y. & Song, M. (2010). Phosphorus Sulfur Silicon Relat. Elem. 185, 2418-2425.]); Yang et al. (2012[Yang, L., Xiao, Y., He, K., Yuan, J. & Mao, P. (2012). Acta Cryst. E68, o1670.]); Xiao et al. (2012[Xiao, Y., Yang, L., He, K., Yuan, J. & Mao, P. (2012). Acta Cryst. E68, o264.]).

[Scheme 1]

Experimental

Crystal data
  • C28H23BrN2OS

  • Mr = 515.45

  • Orthorhombic, P 21 21 21

  • a = 9.36677 (18) Å

  • b = 15.8434 (3) Å

  • c = 16.1452 (3) Å

  • V = 2395.97 (8) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 3.33 mm-1

  • T = 291 K

  • 0.3 × 0.28 × 0.26 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]) Tmin = 0.853, Tmax = 1.000

  • 8866 measured reflections

  • 4264 independent reflections

  • 4033 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.085

  • S = 1.03

  • 4264 reflections

  • 302 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]); 1834 Friedel pairs

  • Absolute structure parameter: -0.004 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1i 0.83 (4) 2.04 (4) 2.838 (3) 162 (4)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5079 ).


Acknowledgements

The authors thank Ms Y. Zhu for technical assistance. This research was supported by the National Natural Science Foundation of P. R. China (No. 21172055) and the High-Level Talents Foundation of Henan University of Technology.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Eseola, A. O., Zhang, M., Xiang, J., Zuo, W., Li, Y., Woods, J. A. O. & Sun, W. (2010). Inorg. Chim. Acta, 363, 1970-1978.  [ISI] [CSD] [CrossRef] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Jiang, B., Wang, X., Shi, F., Tu, S., Ai, T., Ballew, A. & Li, G. (2009). J. Org. Chem. 74, 9486-9489.  [CrossRef] [PubMed] [ChemPort]
Mao, P., Cai, Y., Xiao, Y., Yang, L., Xue, Y. & Song, M. (2010). Phosphorus Sulfur Silicon Relat. Elem. 185, 2418-2425.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wu, X., Jiang, R., Xu, X., Su, X., Lu, W. & Ji, S. (2010). J. Comb. Chem. 12, 829-835.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Xiao, Y., Yang, L., He, K., Yuan, J. & Mao, P. (2012). Acta Cryst. E68, o264.  [CSD] [CrossRef] [details]
Yang, L., Xiao, Y., He, K., Yuan, J. & Mao, P. (2012). Acta Cryst. E68, o1670.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o1379  [ doi:10.1107/S1600536813021016 ]

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