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Volume 69 
Part 12 
Page o1858  
December 2013  

Received 11 November 2013
Accepted 25 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.045
wR = 0.127
Data-to-parameter ratio = 14.2
Details
Open access

(S)-4,5-Diphenyl-1-[1-phenyl-3-(phenyl­sulfan­yl)propan-2-yl]-2-(thio­phen-2-yl)-1H-imidazole

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, C34H28N2S2, the central imidazole ring (r.m.s. deviation = 0.0015 Å) forms dihedral angles of 55.7 (3), 17.94 (11) and 86.27 (11)°, respectively, with the mean planes of the attached thienyl and two phenyl substituents. The thienyl ring shows ring-flip disorder [occupancy ratio = 0.647 (2):0.353 (2)]. The chiral centre maintains the S configuration of the L-phenyl­alaninol starting material. Intra- and inter­molecular C-H...S hydrogen bonds involving the disordered thienyl ring are observed.

Related literature

For the synthesis of aryl sulfides, see: Mispelaere-Canivet et al. (2005[Mispelaere-Canivet, C., Spindler, J. F., Perrio, S. & Beslin, P. (2005). Tetrahedron, 61, 5253-5259.]); Zhang et al. (2007[Zhang, Y., Ngeow, K. C. & Ying, J. Y. (2007). Org. Lett. 9, 3495-3498.]); Wu et al. (2009[Wu, J. R., Lin, C. H. & Lee, C. F. (2009). Chem. Commun. pp. 4450-4452.]); Lv & Bao (2007[Lv, X. & Bao, W. L. (2007). J. Org. Chem. 72, 3863-3867.]). 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, 2418-2415.]); 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.]); Gao et al. (2013[Gao, J., Yang, L., Mai, W., Yuan, J. & Mao, P. (2013). Acta Cryst. E69, o1379.]).

[Scheme 1]

Experimental

Crystal data
  • C34H28N2S2

  • Mr = 528.70

  • Orthorhombic, P 21 21 21

  • a = 12.7882 (7) Å

  • b = 13.7906 (6) Å

  • c = 16.0636 (7) Å

  • V = 2832.9 (2) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.89 mm-1

  • T = 291 K

  • 0.26 × 0.23 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.] Tmin = 0.906, Tmax = 1.000

  • 10599 measured reflections

  • 5065 independent reflections

  • 4456 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.127

  • S = 1.03

  • 5065 reflections

  • 356 parameters

  • 18 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2202 Friedel pairs

  • Absolute structure parameter: 0.00 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C21-H21B...S1i 0.97 2.75 3.677 (3) 161
C22-H22...S1A 0.98 2.73 3.468 (5) 132
Symmetry code: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: RZ5094 ).


Acknowledgements

The authors thank Ms Y. Zhu for technical assistance. This research was supported by the Graduate Student Innovation Fund of Henan University of Technology (No. 2012YJCX33).

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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Gao, J., Yang, L., Mai, W., Yuan, J. & Mao, P. (2013). Acta Cryst. E69, o1379.  [CrossRef] [IUCr Journals]
Lv, X. & Bao, W. L. (2007). J. Org. Chem. 72, 3863-3867.  [CrossRef] [PubMed] [ChemPort]
Mao, P., Cai, Y., Xiao, Y., Yang, L., Xue, Y. & Song, M. (2010). Phosphorus Sulfur Silicon Relat. Elem. 185, 2418-2415.  [CrossRef] [ChemPort]
Mispelaere-Canivet, C., Spindler, J. F., Perrio, S. & Beslin, P. (2005). Tetrahedron, 61, 5253-5259.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wu, J. R., Lin, C. H. & Lee, C. F. (2009). Chem. Commun. pp. 4450-4452.  [CrossRef]
Xiao, Y., Yang, L., He, K., Yuan, J. & Mao, P. (2012). Acta Cryst. E68, o264.  [CSD] [CrossRef] [IUCr Journals]
Yang, L., Xiao, Y., He, K., Yuan, J. & Mao, P. (2012). Acta Cryst. E68, o1670.  [CSD] [CrossRef] [IUCr Journals]
Zhang, Y., Ngeow, K. C. & Ying, J. Y. (2007). Org. Lett. 9, 3495-3498.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1858  [ doi:10.1107/S1600536813032066 ]

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