Methyl 2-(2-bromo­benzyl­idene)-5-(4-hy­droxy­phen­yl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate

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

doi:10.1107/S1600536812013311

Volume 68
Part 4
Pages o1257-o1258
April 2012

Received 5 March 2012
Accepted 27 March 2012
Online 31 March 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R = 0.059
wR = 0.178
Data-to-parameter ratio = 15.4
Details

Methyl 2-(2-bromobenzylidene)-5-(4-hydroxyphenyl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thiazolo[3,2-a]pyrimidine-6-carboxylate

H. Nagarajaiah,^a Nikhath Fathima ^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, C₂₂H₁₇BrN₂O₄S, the central dihydropyrimidine ring, with a chiral C atom, is significantly puckered and adopts a half-chair conformation with the chiral C atom displaced from the mean plane of the remaining ring atoms by 0.305 (6) Å. The hydroxy-phenyl ring is positioned axially to the pyrimidine ring and almost bisects it, the dihedral angle between the mean-planes of the two rings being 89.78 (12)°. The methoxycarbonyl group is disordered over two sites with an occupancy ratio of 0.568 (5):0.432 (5), resulting in a major and a minor conformer. In the crystal, O-HN and C-HS interactions result in sheets along the c axis. The supramolecular assembly is stabilized by [pi] - [pi] stacking interactions between the 2-bromobenzylidene and thiazolopyrimidine rings [centroid-centroid distance = 3.632 (1) Å]. In addition, C-H [pi] interactions are also observed in the crystal structure.

Related literature

For therapeutic and medicinal properties of thiazolopyrimidine derivatives, see: Kappe (2000); Ozair et al. (2010). For a related structure, see: Nagarajaiah & Begum (2011).

Experimental

Crystal data

C₂₂H₁₇BrN₂O₄S
M_r = 485.35
Monoclinic, P 2₁ /c
a = 9.851 (2) Å
b = 23.461 (6) Å
c = 9.416 (2) Å
= 111.229 (5)°
V = 2028.5 (8) Å³
Z = 4
Mo K radiation
= 2.16 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 = 0.697, T_max = 0.724
12267 measured reflections
4409 independent reflections
2563 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.059
wR(F²) = 0.178
S = 1.04
4409 reflections
286 parameters
H-atom parameters constrained
_max = 1.04 e Å^-3
_min = -0.87 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10-C15 benzene ring.

D-HA	D-H	HA	DA	D-HA
O4-H4N2ⁱ	0.82	1.96	2.782 (4)	178
C4B-H4B1S1ⁱⁱ	0.96	2.80	3.621 (12)	144
C1-H1CCg1ⁱⁱⁱ	0.96	2.78	3.585 (5)	142
Symmetry codes: (i) x, y, z-1; (ii) x-1, y, z-1; (iii) $[x-1, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

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: PV2521 ).

Acknowledgements

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

References

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.
Nagarajaiah, H. & Begum, N. S. (2011). Acta Cryst. E67, o3444.
Ozair, A., Suroor, A. K., Nadeem, S. & Waquar, A. (2010). Med. Chem. Res. 19, 1245-1258.
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