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Volume 69 
Part 8 
Page o1262  
August 2013  

Received 24 June 2013
Accepted 10 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.096
Data-to-parameter ratio = 15.9
Details
Open access

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

aDepartment of Chemistry, Bangalore University, Bangalore 560 001, India
Correspondence e-mail: noorsb@rediffmail.com, noorsb05@gmail.com

In the title molecule, C24H19BrN2O5S, the pyrimidine ring is in a flattened half-chair conformation and the 4-acetoxyphenyl group is substituted axially to this ring. The thiazole ring is essentially planar [with a maximum deviation of 0.012 (2) Å for the N atom] and forms dihedral angles of 17.65 (13) and 88.95 (11)° with the bromo- and acetoxy-substituted benzene rings, respectively. The dihedral angle between the benzene rings is 81.84 (13) Å. In the crystal, pairs of weak C-H...O hydrogen bonds lead to the formation of inversion dimers. A weak C-H...[pi] interaction and [pi]-[pi] stacking interactions with centroid-centroid distances of 3.5903 (14) Å are observed.

Related literature

For the biological activity of dihydropyrimidines, see: Alam et al. (2010[Alam, O., Khan, S. A., Siddiqui, N. & Ahsan, W. (2010). Med. Chem. Res. 19, 1245-1258.]); Kappe (2000[Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043-1052.]); Atwal et al. (1991[Atwal, K. S., Swanson, B. N., Unger, S. E., Floyd, D. M., Moreland, S., Hedberg, A. & O'Reilly, B. C. (1991). J. Med. Chem. 34, 806-811.]); Rovnyak et al. (1992[Rovnyak, G. C., Atwal, K. S., Hedberg, A., Kimball, S. D., Moreland, S., Gougoutas, J. Z., O'Reilly, B. C., Schwartz, J. & Malley, M. F. (1992). J. Med. Chem. 35, 3254-3263.]). For related structures, see: Nagarajaiah et al. (2011[Nagarajaiah, H. & Begum, N. S. (2011). Acta Cryst. E67, o3444.], 2012[Nagarajaiah, H., Fathima, N. & Begum, N. S. (2012). Acta Cryst. E68, o1257-o1258.]). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C24H19BrN2O5S

  • Mr = 527.38

  • Triclinic, [P \overline 1]

  • a = 7.6018 (5) Å

  • b = 11.9648 (7) Å

  • c = 14.0877 (9) Å

  • [alpha] = 106.425 (1)°

  • [beta] = 104.700 (2)°

  • [gamma] = 106.296 (1)°

  • V = 1099.75 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.00 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, Wisconsin, USA.]) Tmin = 0.714, Tmax = 0.740

  • 9029 measured reflections

  • 4777 independent reflections

  • 3989 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.096

  • S = 1.05

  • 4777 reflections

  • 301 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.58 e Å-3

  • [Delta][rho]min = -0.61 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C5-C7/C9/N1/N2 ring.

D-H...A D-H H...A D...A D-H...A
C13-H13...O1i 0.93 2.60 3.343 (4) 138
C10-H10...Cgii 0.93 2.61 3.513 (4) 147
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x-1, -y-1, -z-1.

Data collection: SMART (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5628 ).


Acknowledgements

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

References

Alam, O., Khan, S. A., Siddiqui, N. & Ahsan, W. (2010). Med. Chem. Res. 19, 1245-1258.  [Web of Science] [CrossRef] [ChemPort]
Atwal, K. S., Swanson, B. N., Unger, S. E., Floyd, D. M., Moreland, S., Hedberg, A. & O'Reilly, B. C. (1991). J. Med. Chem. 34, 806-811.  [CrossRef] [PubMed] [ChemPort] [Web of Science]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. 34, 1555-1573.  [ChemPort]
Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kappe, C. O. (2000). Eur. J. Med. Chem. 35, 1043-1052.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Nagarajaiah, H. & Begum, N. S. (2011). Acta Cryst. E67, o3444.  [CSD] [CrossRef] [IUCr Journals]
Nagarajaiah, H., Fathima, N. & Begum, N. S. (2012). Acta Cryst. E68, o1257-o1258.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Rovnyak, G. C., Atwal, K. S., Hedberg, A., Kimball, S. D., Moreland, S., Gougoutas, J. Z., O'Reilly, B. C., Schwartz, J. & Malley, M. F. (1992). J. Med. Chem. 35, 3254-3263.  [CrossRef] [PubMed] [ChemPort] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England.


Acta Cryst (2013). E69, o1262  [ doi:10.1107/S1600536813019132 ]

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