(E)-Ethyl 2-anilino-5-[3-(dimethyl­amino)­acrylo­yl]-4-phenyl­thio­phene-3-carboxyl­ate

Mabkhot, Y.N.; Barakat, A.; Alatibi, F.; Choudhary, M.I.; Yousuf, S.

doi:10.1107/S1600536813003231

Volume 69
Part 3
Page o351
March 2013

Received 28 January 2013
Accepted 31 January 2013
Online 6 February 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.003 Å
R = 0.047
wR = 0.142
Data-to-parameter ratio = 15.2
Details

(E)-Ethyl 2-anilino-5-[3-(dimethylamino)acryloyl]-4-phenylthiophene-3-carboxylate

Yahia Nasser Mabkhot,^a ^* Assem Barakat,^a,^b Fatima Alatibi,^a M. Iqbal Choudhary ^c,^a and Sammer Yousuf ^c ^*

^aDepartment of Chemistry, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia,^bDepartment of Chemistry, Faculty of Science, Alexandria University, PO Box 426, Ibrahimia, 21321 Alexandria, Egypt, and ^cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: yahia@ksu.edu.sa, dr.sammer.yousuf@gmail.com

In the title compound, C₂₄H₂₄N₂O₃S, the phenyl rings form dihedral angles of 55.65 (11) and 79.60 (11)° with the plane of the thiophene ring. The molecular conformation is stabilized by an intramolecular N-HO hydrogen bond, generating an S(6) ring motif. In the crystal, centrosymmetrically related molecules are linked into dimers by two pairs of C-HO interactions.

Related literature

For background to biological activity of thiophene derivatives see: Mishra et al. (2011). For the synthesis of different thiophene derivatives, see: Mabkhot et al. (2011); Mabkhot, Barakat & Alshahrani (2012); Mabkhot, Barakat, Al-Majid, Alamary & Al-Nahary (2012); Mabkhot, Barakat, Al-Majid & Alshahrani (2012). For related structures, see: Cao et al. (2003).

Experimental

Crystal data

C₂₄H₂₄N₂O₃S
M_r = 420.51
Triclinic, $[P \overline 1]$
a = 6.5776 (9) Å
b = 10.7119 (14) Å
c = 16.516 (2) Å
= 78.459 (3)°
= 79.743 (3)°
= 80.765 (3)°
V = 1112.5 (3) Å³
Z = 2
Mo K radiation
= 0.17 mm^-1
T = 273 K
0.28 × 0.27 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.953, T_max = 0.970
12618 measured reflections
4123 independent reflections
3373 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.142
S = 1.05
4123 reflections
272 parameters
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO2	0.86	2.07	2.709 (3)	130
C19-H19AO3ⁱ	0.93	2.42	3.294 (3)	157
C21-H21AO3ⁱ	0.96	2.60	3.491 (4)	155
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5041 ).

Acknowledgements

This project was supported by King Saud University, Deanship of Scientific Research, College of Science Research Center.

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cao, K.-G., Wang, Z.-W., Zhao, X.-Q. & Fang, T. (2003). Chin. J. Org. Chem. 23, 1411-1415.
Mabkhot, Y. N., Barakat, A., Al-Majid, A. M., Alamary, A. S. & Al-Nahary, T. T. (2012). Int. J. Mol. Sci. 13, 5035-5047.
Mabkhot, Y. N., Barakat, A., Al-Majid, A. M., Al-Othman, Z. A. & Alamary, A. S. (2011). Int. J. Mol. Sci. 12, 7824-7834.
Mabkhot, Y. N., Barakat, A., Al-Majid, A. M. & Alshahrani, S. A. (2012). Int. J. Mol. Sci. 13, 2263-2275.
Mabkhot, Y. N., Barakat, A. & Alshahrani, S. (2012). J. Mol. Struct., 1027, 15-19.
Mishra, R., Tomar, I., Singhal, S. & Jha, K. K. (2011). Pharma Chem. 3, 38-54.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds