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Volume 69 
Part 11 
Pages o1653-o1654  
November 2013  

Received 1 October 2013
Accepted 10 October 2013
Online 19 October 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.031
wR = 0.081
Data-to-parameter ratio = 12.8
Details
Open access

2-(4-Chloro­phen­yl)-4-phenyl-1,2-di­hydro­quinazoline

aLaboratoire de Synthèse des Molécules d'Intérêts Biologiques, Département de Chimie, Faculté des Sciences Exactes, Université de Constantine 1, 25000 Constantine, Algeria,bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine 1, 25000 , Algeria, and cDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi 04000, Algeria
Correspondence e-mail: bouacida_sofiane@yahoo.fr

In the title compound, C20H15ClN2, the pyrimidine ring is in a flattened half-chair conformation. The phenyl and chloro-substituted benzene rings form dihedral angles of 84.97 (5) and 80.23 (4)°, respectively, with the benzene ring of the di­hydro­quinazoline group. The dihedral angle between the phenyl and chloro-substituted benzene rings is 61.71 (5)°. In the crystal, mol­ecules are arranged in inter­secting layers parallel to (101) and (-102), with N-H...N hydrogen bonds linking mol­ecules along [010]. In addition, a weak C-H...[pi] inter­action is observed.

Related literature

For the preparation and applications of quinazoline derivatives, see: Gundla et al. (2008[Gundla, R., Kazemi, R., Sanam, R., Muttineni, R., Sarma, J. A. R. P., Dayam, R. & Neamati, N. (2008). J. Med. Chem. 51, 3367-3377.]); Luth & Lowe (2008[Luth, A. & Lowe, W. (2008). Eur. J. Med. Chem. 43, 1478-1488.]); Fry et al. (1994[Fry, D. W., Kraker, A. J., McMichael, A., Ambroso, L. A., Nelson, J. M., Leopold, W. R., Connors, R. W. & Bridges, A. (1994). J. Sci. 265, 1093-1095.]); Kunes et al. (2000[Kunes, J., Pour, M., Waisser, K., Slosarek, M. & Janota, J. (2000). Il Farmaco, 55, 725-729.]); Michael (2002[Michael, J. P. (2002). Nat. Prod. Rep. 19, 742-760.]); Frère et al. (2003[Frère, S., Thierry, V., Bailly, C. & Besson, T. (2003). Tetrahedron, 59, 773-779.]); Langer & Bodtke (2003[Langer, P. & Bodtke, A. (2003). Tetrahedron Lett. 44, 5965-5967.]).

[Scheme 1]

Experimental

Crystal data
  • C20H15ClN2

  • Mr = 318.79

  • Monoclinic, P 21 /c

  • a = 9.2563 (10) Å

  • b = 10.6283 (11) Å

  • c = 17.6230 (19) Å

  • [beta] = 116.775 (7)°

  • V = 1547.8 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 150 K

  • 0.18 × 0.04 × 0.03 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2002[Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.]) Tmin = 0.948, Tmax = 1.000

  • 8914 measured reflections

  • 2724 independent reflections

  • 2462 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.081

  • S = 1.05

  • 2724 reflections

  • 212 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C15-C20 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1N...N2i 0.830 (19) 2.316 (19) 3.1234 (18) 164.3 (19)
C11-H11...Cgii 0.93 2.76 3.666 (2) 165
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x-1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2011[Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); 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 DIAMOND (Brandenburg & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.]); 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: LH5660 ).


Acknowledgements

We are grateful to all the personnel of the LSMIB laboratory and UR-CHEMS, Université Constantine 1, Algeria, for their assistance. Thanks are due to the MESRS (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique, Algeria) for financial support.

References

Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact, Bonn, Germany.
Bruker (2011). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Frère, S., Thierry, V., Bailly, C. & Besson, T. (2003). Tetrahedron, 59, 773-779.
Fry, D. W., Kraker, A. J., McMichael, A., Ambroso, L. A., Nelson, J. M., Leopold, W. R., Connors, R. W. & Bridges, A. (1994). J. Sci. 265, 1093-1095.  [CrossRef] [ChemPort]
Gundla, R., Kazemi, R., Sanam, R., Muttineni, R., Sarma, J. A. R. P., Dayam, R. & Neamati, N. (2008). J. Med. Chem. 51, 3367-3377.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Kunes, J., Pour, M., Waisser, K., Slosarek, M. & Janota, J. (2000). Il Farmaco, 55, 725-729.  [PubMed] [ChemPort]
Langer, P. & Bodtke, A. (2003). Tetrahedron Lett. 44, 5965-5967.  [Web of Science] [CrossRef] [ChemPort]
Luth, A. & Lowe, W. (2008). Eur. J. Med. Chem. 43, 1478-1488.  [Web of Science] [PubMed]
Michael, J. P. (2002). Nat. Prod. Rep. 19, 742-760.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2002). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1653-o1654   [ doi:10.1107/S1600536813027839 ]

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