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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 [sigma](C-C) = 0.007 Å
Disorder in main residue
R = 0.059
wR = 0.178
Data-to-parameter ratio = 15.4
Details
Open access

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

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-H...N and C-H...S 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[Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043-1052.]); Ozair et al. (2010[Ozair, A., Suroor, A. K., Nadeem, S. & Waquar, A. (2010). Med. Chem. Res. 19, 1245-1258.]). For a related structure, see: Nagarajaiah & Begum (2011[Nagarajaiah, H. & Begum, N. S. (2011). Acta Cryst. E67, o3444.]).

[Scheme 1]

Experimental

Crystal data
  • C22H17BrN2O4S

  • Mr = 485.35

  • Monoclinic, P 21 /c

  • a = 9.851 (2) Å

  • b = 23.461 (6) Å

  • c = 9.416 (2) Å

  • [beta] = 111.229 (5)°

  • V = 2028.5 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.]) Tmin = 0.697, Tmax = 0.724

  • 12267 measured reflections

  • 4409 independent reflections

  • 2563 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.178

  • S = 1.04

  • 4409 reflections

  • 286 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.04 e Å-3

  • [Delta][rho]min = -0.87 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-H...A D-H H...A D...A D-H...A
O4-H4...N2i 0.82 1.96 2.782 (4) 178
C4B-H4B1...S1ii 0.96 2.80 3.621 (12) 144
C1-H1C...Cg1iii 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[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA.]); data reduction: SAINT-Plus; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


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.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [details]
Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043-1052.  [ISI] [CrossRef] [PubMed] [ChemPort]
Nagarajaiah, H. & Begum, N. S. (2011). Acta Cryst. E67, o3444.  [CrossRef] [details]
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.  [CrossRef] [details]
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.


Acta Cryst (2012). E68, o1257-o1258   [ doi:10.1107/S1600536812013311 ]

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