Ethyl 3-acetyl-4-(3-meth­oxy­phen­yl)-6-methyl-2-sulfanyl­idene-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

Fathima, N.; Nagarajaiah, H.; Begum, N.S.

doi:10.1107/S1600536812017679

Volume 68
Part 5
Page o1555
May 2012

Received 31 March 2012
Accepted 20 April 2012
Online 28 April 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.063
wR = 0.204
Data-to-parameter ratio = 16.8
Details

Ethyl 3-acetyl-4-(3-methoxyphenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Nikhath Fathima,^a H Nagarajaiah ^a and Noor Shahina Begum ^a ^*

^aDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, Karnataka, India
Correspondence e-mail: noorsb@rediffmail.com

In the title compound, C₁₇H₂₀N₂O₄S, the aryl ring is positioned perpendicular to the dihydropyrimidine ring, the dihedral angle between the ring planes being 77.48 (9)°. The carboxylate and methyl groups are in a cis conformation with respect to the C=C bond. The dihydropyrimidine ring adopts a twist-boat conformation. The crystal structure is stabilized by N-HO and C-HO interactions, the former resulting in molecular chains along the b axis and the latter forming inversion dimers.

Related literature

For the biological activity of dihydropyrimidines, see: Kappe (2000). For a related structure, see: Begum & Vasundhara (2009).

Experimental

Crystal data

C₁₇H₂₀N₂O₄S
M_r = 348.41
Monoclinic, P 2₁ /n
a = 11.515 (2) Å
b = 7.3687 (16) Å
c = 20.049 (4) Å
= 90.960 (4)°
V = 1701.0 (6) Å³
Z = 4
Mo K radiation
= 0.21 mm^-1
T = 296 K
0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998) T_min = 0.963, T_max = 0.967
10054 measured reflections
3707 independent reflections
2545 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.063
wR(F²) = 0.204
S = 1.03
3707 reflections
221 parameters
H-atom parameters constrained
_max = 0.34 e Å^-3
_min = -0.43 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O3ⁱ	0.86	2.07	2.907 (3)	164
C3-H3BO1ⁱⁱ	0.96	2.60	3.393 (4)	140
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2529 ).

Acknowledgements

NSB is thankful to the University Grants Commission (UGC), India, for financial assistance.

References

Begum, N. S. & Vasundhara, D. E. (2009). J. Chem. Res. 4, 201-204.
Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043-1052.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.

organic compounds