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Volume 69 
Part 7 
Page o1111  
July 2013  

Received 29 May 2013
Accepted 10 June 2013
Online 19 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
Disorder in main residue
R = 0.064
wR = 0.191
Data-to-parameter ratio = 12.4
Details
Open access

Methyl 3-[(6-nitro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)sulfanyl]propanoate

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,bDepartment of Medicinal Chemistry., Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt,cDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt, and dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, C18H15N3O5S, the approximately planar quinazoline ring system [maximum deviation = 0.097 (3) Å] forms a dihedral angle of 76.53 (19)° with the phenyl ring. The terminal -C(=O)-O-C group is disordered over two sets of sites with a site-occupancy ratio of 0.811 (17):0.189 (17). In the crystal, molecules are linked via weak C-H...O hydrogen bonds into sheets parallel to the ac plane.

Related literature

For background to quinazoline chemistry, see: El-Azab (2007[El-Azab, A. S. (2007). Phosphorus Sulfur Silicon, 182, 333-348.]); El-Azab et al. (2010[El-Azab, A. S., Al-Omar, M. A., Abdel-Aziz, A. A., Abdel-Aziz, N. I., El-Sayed, M. A., Aleisa, A. M., Sayed-Ahmed, M. M. & Abdel-Hamid, S. G. (2010). Eur. J. Med. Chem. 45, 4188-4198.], 2011[El-Azab, A. S., ElTahir, K. H. & Attia, S. M. (2011). Monatsh. Chem. 142, 837-848.]); Alafeefy et al. (2008[Alafeefy, A. M., Kadi, A. A., El-Azab, A. S., Abdel-Hamide, S. G. & Daba, M. H. (2008). Arch. Pharm. (Weinheim), 341, 377-385.]); Al-Suwaidan et al. (2013[Al-Suwaidan I. A, Alanazi, A. M. Abdel-Aziz, A. A.-M., Mohamed, M. A. & El-Azab, A. S. (2013). Bioorg. Med. Chem. Lett. 23, 3935-3941.]); El-Azab & ElTahir (2012a[El-Azab, A. S. & ElTahir, K. H. (2012a). Bioorg. Med. Chem. Lett. 22, 327-333.],b[El-Azab, A. S. & ElTahir, K. H. (2012b). Bioorg. Med. Chem. Lett. 22, 1879-1885.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C18H15N3O5S

  • Mr = 385.39

  • Monoclinic, P 21 /n

  • a = 4.9146 (3) Å

  • b = 26.5065 (18) Å

  • c = 14.0900 (9) Å

  • [beta] = 94.645 (4)°

  • V = 1829.5 (2) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.89 mm-1

  • T = 296 K

  • 0.32 × 0.26 × 0.13 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.583, Tmax = 0.791

  • 12669 measured reflections

  • 3382 independent reflections

  • 1861 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.064

  • wR(F2) = 0.191

  • S = 1.03

  • 3382 reflections

  • 273 parameters

  • 9 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6A...O2i 0.93 2.56 3.142 (5) 121
C10-H10A...O2ii 0.93 2.39 3.167 (5) 140
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5622 ).


Acknowledgements

The authors thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University. CSC thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

References

Alafeefy, A. M., Kadi, A. A., El-Azab, A. S., Abdel-Hamide, S. G. & Daba, M. H. (2008). Arch. Pharm. (Weinheim), 341, 377-385.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Al-Suwaidan I. A, Alanazi, A. M. Abdel-Aziz, A. A.-M., Mohamed, M. A. & El-Azab, A. S. (2013). Bioorg. Med. Chem. Lett. 23, 3935-3941.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Azab, A. S. (2007). Phosphorus Sulfur Silicon, 182, 333-348.  [ChemPort]
El-Azab, A. S., Al-Omar, M. A., Abdel-Aziz, A. A., Abdel-Aziz, N. I., El-Sayed, M. A., Aleisa, A. M., Sayed-Ahmed, M. M. & Abdel-Hamid, S. G. (2010). Eur. J. Med. Chem. 45, 4188-4198.  [Web of Science] [ChemPort] [PubMed]
El-Azab, A. S. & ElTahir, K. H. (2012a). Bioorg. Med. Chem. Lett. 22, 327-333.  [ChemPort] [PubMed]
El-Azab, A. S. & ElTahir, K. H. (2012b). Bioorg. Med. Chem. Lett. 22, 1879-1885.  [ChemPort] [PubMed]
El-Azab, A. S., ElTahir, K. H. & Attia, S. M. (2011). Monatsh. Chem. 142, 837-848.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1111  [ doi:10.1107/S1600536813016127 ]

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