[Journal logo]

Volume 69 
Part 7 
Page o1113  
July 2013  

Received 7 June 2013
Accepted 12 June 2013
Online 19 June 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.101
Data-to-parameter ratio = 16.0
Details
Open access

2-(1,3-Benzodioxol-5-yl)-3-phenylquinazolin-4(3H)-one

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India,bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India, and cDepartment of Physics, St Philomena's College, Mysore, India
Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

In the molecule of the title compound, C21H14N2O3, the quinazoline ring system [maximum deviation = 0.076 (1) Å] makes dihedral angles of 40.57 (9) and 42.31 (11)°, respectively, with the phenyl and 1,3-benzodioxole rings. The dihedral angle between the phenyl ring and the 1,3-benzodioxole ring is 4.34 (10)°. In the crystal, C-H...O hydrogen bonds link the molecules into infinite zigzag chains extending along [100].

Related literature

For the biological and pharmaceutical importance of quinazolines, see: Arfan et al. (2008[Arfan, M., Khan, R., Imran, M., Khan, H. & Mehmood, J. (2008). J. Chem. Soc. Pak. 30, 299-305.]); Bartroli et al. (1998[Bartroli, J., Turmo, E., Alguero, M., Boncompte, E., Vericat, M. L., Conte, L., Ramis, J., Merlos, M., Garcia-Rafanell, J. & Forn, J. (1998). J. Med. Chem. 41, 1869-1882.]); Kung et al. (1999[Kung, P. P., Casper, M. D., Cook, K. L., Wilson-Lingardo, L., Risen, L. M., Vickers, T. A., Ranken, R., Blyn, L. B., Wyatt, J. R., Cook, P. & Decker, D. J. (1999). J. Med. Chem. 42, 4705-4713.]); Mannschreck et al. (1984[Mannschreck, A., Koller, H., Stuhler, G., Davis, M. A. & Traber, J. (1984). Eur. J. Med. Chem. 19, 381-383.]).

[Scheme 1]

Experimental

Crystal data
  • C21H14N2O3

  • Mr = 342.34

  • Monoclinic, P 21

  • a = 8.984 (4) Å

  • b = 6.056 (3) Å

  • c = 15.248 (6) Å

  • [beta] = 95.357 (6)°

  • V = 826.0 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 273 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • 9157 measured reflections

  • 3751 independent reflections

  • 3163 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.101

  • S = 1.04

  • 3751 reflections

  • 235 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C17-H17...O5i 0.93 2.37 3.185 (3) 146
C25-H23A...O5ii 0.97 2.49 3.416 (3) 160
Symmetry codes: (i) x, y+1, z; (ii) x-1, y+1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2072 ).


Acknowledgements

Chandra would like to thank the University of Mysore for the award of an RFSMS fellowship under the head DV5/Physics/389/RFSMS/2009-2010/10.07.2012.

References

Arfan, M., Khan, R., Imran, M., Khan, H. & Mehmood, J. (2008). J. Chem. Soc. Pak. 30, 299-305.  [ChemPort]
Bartroli, J., Turmo, E., Alguero, M., Boncompte, E., Vericat, M. L., Conte, L., Ramis, J., Merlos, M., Garcia-Rafanell, J. & Forn, J. (1998). J. Med. Chem. 41, 1869-1882.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kung, P. P., Casper, M. D., Cook, K. L., Wilson-Lingardo, L., Risen, L. M., Vickers, T. A., Ranken, R., Blyn, L. B., Wyatt, J. R., Cook, P. & Decker, D. J. (1999). J. Med. Chem. 42, 4705-4713.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Mannschreck, A., Koller, H., Stuhler, G., Davis, M. A. & Traber, J. (1984). Eur. J. Med. Chem. 19, 381-383.  [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, o1113  [ doi:10.1107/S1600536813016346 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.