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Volume 70 
Part 1 
Page o8  
January 2014  

Received 24 November 2013
Accepted 26 November 2013
Online 4 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.010 Å
R = 0.086
wR = 0.230
Data-to-parameter ratio = 17.3
Details
Open access

(E)-2-Methyl-3-phenyl­selanyl-4-(phenyl­sulfin­yl)oct-3-en-2-ol

aCollege of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009, People's Republic of China,bNational Engineering Technique Research Center for Biotechnology, Nanjing 211816, People's Republic of China, and cResearch Institute of Benzene Chemical, Research Institute of Nanjing Chemical Industry Group, No. 699 Geguan Road, Dachang, Nanjing 210044, People's Republic of China
Correspondence e-mail: cccnhy@163.com

In the title compound, C21H26O2SSe, the S atom adopts a pyramidal geometry (bond-angle sum = 304°) and the n-butyl chain shows an extended conformation. An intra­molecular C-H...O hydrogen bond closes an S(8) ring. In the crystal, inversion dimers are formed with molecules linked by pairs of O-H...O=S hydrogen bonds, generating R22(14) loops. Weak C-H...O inter­actions also occur.

Related literature

For background to the title compound, see: Uma et al. (2003[Uma, R., Crevisy, C. & Gree, R. (2003). Chem. Rev. 103, 27-52.]). For the synthesis, see: He et al. (2007[He, G., Zhou, C., Fu, C. & Ma, S. (2007). Tetrahedron, 63, 3800-3805.]).

[Scheme 1]

Experimental

Crystal data
  • C21H26O2SSe

  • Mr = 421.44

  • Monoclinic, P 21 /c

  • a = 12.869 (3) Å

  • b = 19.445 (4) Å

  • c = 8.3702 (18) Å

  • [beta] = 100.280 (4)°

  • V = 2061.0 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.93 mm-1

  • T = 293 K

  • 0.49 × 0.20 × 0.05 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.590, Tmax = 1.000

  • 11048 measured reflections

  • 4029 independent reflections

  • 2554 reflections with I > 2[sigma](I)

  • Rint = 0.130

Refinement
  • R[F2 > 2[sigma](F2)] = 0.086

  • wR(F2) = 0.230

  • S = 1.01

  • 4029 reflections

  • 233 parameters

  • 1 restraint

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

  • [Delta][rho]max = 1.99 e Å-3

  • [Delta][rho]min = -0.56 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.85 (9) 1.91 (8) 2.737 (6) 167 (10)
C11-H11...O1 0.93 2.50 3.180 (7) 130
C15-H15...O2ii 0.93 2.60 3.463 (7) 155
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7167 ).


Acknowledgements

The authors thank the Center of Test and Analysis, Nanjing University, for the data collection.

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
He, G., Zhou, C., Fu, C. & Ma, S. (2007). Tetrahedron, 63, 3800-3805.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Uma, R., Crevisy, C. & Gree, R. (2003). Chem. Rev. 103, 27-52.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2014). E70, o8  [ doi:10.1107/S1600536813032182 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.