[Journal logo]

Volume 68 
Part 12 
Page o3275  
December 2012  

Received 18 October 2012
Accepted 27 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.032
wR = 0.080
Data-to-parameter ratio = 14.9
Details
Open access

Ethyl 2-cyano-5-oxo-5-(thiophen-2-yl)-3-(3,4,5-trimethoxyphenyl)pentanoate

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India,bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and cDepartment of Physics, Faculty of Science, An Najah National University, Nabtus West Bank, Palestinian Territories
Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

In the title compound, C21H23NO6S, the dihedral angle between the thiopene and benzene rings is 88.66 (6)°. In the crystal, molecules are connected by C-H...N and C-H...O hydrogen bonds, forming a tape along [10-1]. In addition, C-H...[pi] and [pi]-[pi] stacking [centroid-centroid distance = 3.879 (2) Å between the thiophene rings] interactions are observed.

Related literature

For applications of thiophenes, see: Günther & Steinmetz (1963[Günther, O. S. & Steinmetz, R. (1963). Liebigs Ann. Chem. 668, 19-30.]). For a similar structure, see: Harrison et al. (2010[Harrison, W. T. A., Chidan Kumar, C. S., Yathirajan, H. S., Ashalatha, B. V. & Narayana, B. (2010). Acta Cryst. E66, o2477.]).

[Scheme 1]

Experimental

Crystal data
  • C21H23NO6S

  • Mr = 417.47

  • Triclinic, [P \overline 1]

  • a = 8.4308 (5) Å

  • b = 10.5025 (6) Å

  • c = 12.3059 (6) Å

  • [alpha] = 98.530 (2)°

  • [beta] = 107.950 (2)°

  • [gamma] = 97.966 (3)°

  • V = 1005.26 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 296 K

  • 0.22 × 0.20 × 0.19 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • 16712 measured reflections

  • 3965 independent reflections

  • 3498 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.080

  • S = 1.04

  • 3965 reflections

  • 266 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8-C13 ring.

D-H...A D-H H...A D...A D-H...A
C3-H3...N1i 0.93 2.49 3.368 (2) 157
C18-H18B...O2ii 0.96 2.56 3.385 (2) 143
C17-H17A...Cg2iii 0.96 2.85 3.6327 (16) 139
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: Mercury.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5211 ).


Acknowledgements

SMK thanks the UGC-BRS and the University of Mysore for the award of a fellowship.

References

Günther, O. S. & Steinmetz, R. (1963). Liebigs Ann. Chem. 668, 19-30.
Harrison, W. T. A., Chidan Kumar, C. S., Yathirajan, H. S., Ashalatha, B. V. & Narayana, B. (2010). Acta Cryst. E66, o2477.  [CSD] [CrossRef] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3275  [ doi:10.1107/S1600536812044522 ]

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.