[Journal logo]

Volume 69 
Part 5 
Page o713  
May 2013  

Received 1 April 2013
Accepted 8 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.098
Data-to-parameter ratio = 15.1
Details
Open access

5-(2-Cyanobenzyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate

aTianjin First Central Hospital, Tianjin 300192, People's Republic of China,bTianjin Medical University, Tianjin 300070, People's Republic of China,cSchool of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, People's Republic of China, and dTianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China
Correspondence e-mail: liudk@tjipr.com

In the title molecule, C17H16N2O2S, the tetrahydropyridine ring exhibits a half-chair conformation. The mean planes of the ester chain and benzene ring are twisted by 5.5 (1) and 81.32 (5)°, respectively, from the plane of thiophene ring. In the crystal, weak C-H...O interactions link molecules related by translation along [100] into chains.

Related literature

For the crystal structures of related compounds, see: Wang et al. (2010[Wang, Z.-M., Zhao, J. & Xu, G. (2010). Acta Cryst. E66, o1354.]); Yang et al. (2012[Yang, J., Chen, N., Sun, H., Cao, X.-X. & Liu, D.-K. (2012). Acta Cryst. E68, o1053.]). For details of the synthesis, see: Zhou et al. (2011[Zhou, Y. S., Wang, P. B., Liu, Y., Chen, J. F., Yue, N. & Liu, D. K. (2011). Acta Pharm. Sin. 46, 70-74.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16N2O2S

  • Mr = 312.38

  • Monoclinic, P 21 /n

  • a = 14.174 (3) Å

  • b = 5.9321 (12) Å

  • c = 18.796 (4) Å

  • [beta] = 99.06 (3)°

  • V = 1560.7 (5) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.91 mm-1

  • T = 113 K

  • 0.26 × 0.24 × 0.22 mm

Data collection
  • Rigaku Saturn diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.636, Tmax = 0.678

  • 16000 measured reflections

  • 3034 independent reflections

  • 2819 reflections with I > 2[sigma](I)

  • Rint = 0.045

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

  • wR(F2) = 0.098

  • S = 1.08

  • 3034 reflections

  • 201 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11...O2i 0.95 2.53 3.3346 (19) 143
Symmetry code: (i) x+1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5399 ).


Acknowledgements

This project was supported by the National Major Scientific and Technological Special Project for "Significant New Drugs Development" (No. 2013ZX09102014). The authors also thank Mr Hai-Bin Song of Nankai University for the X-ray crystallographic determination and helpful suggestions.

References

Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wang, Z.-M., Zhao, J. & Xu, G. (2010). Acta Cryst. E66, o1354.  [CSD] [CrossRef] [details]
Yang, J., Chen, N., Sun, H., Cao, X.-X. & Liu, D.-K. (2012). Acta Cryst. E68, o1053.  [CSD] [CrossRef] [details]
Zhou, Y. S., Wang, P. B., Liu, Y., Chen, J. F., Yue, N. & Liu, D. K. (2011). Acta Pharm. Sin. 46, 70-74.  [ChemPort]


Acta Cryst (2013). E69, o713  [ doi:10.1107/S1600536813009513 ]

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.