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

Prabhuswamy, M.; Madan Kumar, S.; Raghavendra, K.R.; Abdoh, M.M.M.; Shashikanth, S.; Lokanath, N.K.

doi:10.1107/S1600536812044522

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 (C-C) = 0.002 Å
R = 0.032
wR = 0.080
Data-to-parameter ratio = 14.9
Details

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

M. Prabhuswamy,^a S. Madan Kumar,^a K. R. Raghavendra,^b M. M. M. Abdoh,^c S. Shashikanth ^b and N. K. Lokanath ^a ^*

^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-HN and C-HO 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). For a similar structure, see: Harrison et al. (2010).

Experimental

Crystal data

C₂₁H₂₃NO₆S
M_r = 417.47
Triclinic, $[P \overline 1]$
a = 8.4308 (5) Å
b = 10.5025 (6) Å
c = 12.3059 (6) Å
= 98.530 (2)°
= 107.950 (2)°
= 97.966 (3)°
V = 1005.26 (10) Å³
Z = 2
Mo K radiation
= 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(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.080
S = 1.04
3965 reflections
266 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.29 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8-C13 ring.

D-HA	D-H	HA	DA	D-HA
C3-H3N1ⁱ	0.93	2.49	3.368 (2)	157
C18-H18BO2ⁱⁱ	0.96	2.56	3.385 (2)	143
C17-H17ACg2ⁱⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); 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.
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.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds