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Volume 69 
Part 11 
Pages o1719-o1720  
November 2013  

Received 9 October 2013
Accepted 24 October 2013
Online 31 October 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.031
wR = 0.082
Data-to-parameter ratio = 12.9
Details
Open access

2-(2-Chloro-8-methyl­quinolin-3-yl)-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, C24H18ClN3, the di­hydro­quinazoline and methyl-substituted quinoline benzene rings make a dihedral angle of 78.18 (4)° and form dihedral angles of 45.91 (5) and 79.80 (4)°, respectively, with the phenyl ring. The dihedral angle between the phenyl ring of di­hydro­quinazoline and the methyl-substituted benzene ring of quinoline is 78.18 (4)°. The crystal packing can be described as crossed layers parallel to the (011) and (0-11) planes. The structure features N-H...N hydrogen bonds and [pi]-[pi] inter­actions [centroid-centroid distance between phenyl rings = 3.7301 (9) Å].

Related literature

For the preparation and applications of quinazoline and quinoline derivatives, see: Jenekhe et al. (2001[Jenekhe, S. A., Lu, L. & Alam, M. M. (2001). Macromolecules, 34, 7315-7324.]); Hoemann et al. (2000[Hoemann, M. Z., Kumaravel, G., Xie, R. L., Rossi, R. F., Meyer, S., Sidhu, A., Cuny, G. D. & Hauske, J. R. (2000). Bioorg. Med. Chem. Lett. 10, 2675-2678.]); Connolly et al. (2005[Connolly, D. J., Cusack, D., O'Sullivan, T. P. & Guiry, P. J. (2005). Tetrahedron, 61, 10153-10202.]); Besson et al. (2007[Besson, T. & Chosson, E. (2007). Comb. Chem. High Throughput Screening, 10, 903-917.]); Roma et al. (2000[Roma, G., Braccio, M. D., Grossi, G., Mattioli, F. & Ghia, M. (2000). Eur. J. Med. Chem. 35, 1021-1035.]); Chen et al. (2001[Chen, Y.-L., Fang, K.-C., Sheu, J.-Y., Hsu, S.-L. & Tzeng, C.-C. (2001). J. Med. Chem. 44, 2374-2377.]); Debache et al. (2008[Debache, A., Boulcina, R., Belfaitah, A., Rhouati, S. & Carboni, B. (2008). Synlett, pp. 509-512.], 2009[Debache, A., Ghalem, W., Boulcina, R., Belfaitah, A., Rhouati, S. & Carboni, B. (2009). Tetrahedron Lett. 50, 5248-5250.]); Nemouchi et al. (2012[Nemouchi, S., Boulcina, R., Carboni, B. & Debache, A. (2012). C. R. Chim. 15, 394-397.]).

[Scheme 1]

Experimental

Crystal data
  • C24H18ClN3

  • Mr = 383.86

  • Monoclinic, P 21 /c

  • a = 14.4553 (13) Å

  • b = 8.7501 (9) Å

  • c = 16.8630 (16) Å

  • [beta] = 119.696 (6)°

  • V = 1852.8 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 150 K

  • 0.12 × 0.04 × 0.02 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 = 0.959, Tmax = 1.000

  • 10282 measured reflections

  • 3276 independent reflections

  • 2894 reflections with I > 2[sigma](I)

  • Rint = 0.027

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

  • wR(F2) = 0.082

  • S = 1.06

  • 3276 reflections

  • 254 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3N...N2i 0.86 2.26 3.0998 (18) 165
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\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 GbR, 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: HG5353 ).


Acknowledgements

We are grateful to all personnel of the Laboratoire de Synthèse des Molécules d'intérêts Biologiques 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

Besson, T. & Chosson, E. (2007). Comb. Chem. High Throughput Screening, 10, 903-917.  [CrossRef] [ChemPort]
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, 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]
Chen, Y.-L., Fang, K.-C., Sheu, J.-Y., Hsu, S.-L. & Tzeng, C.-C. (2001). J. Med. Chem. 44, 2374-2377.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Connolly, D. J., Cusack, D., O'Sullivan, T. P. & Guiry, P. J. (2005). Tetrahedron, 61, 10153-10202.  [Web of Science] [CrossRef] [ChemPort]
Debache, A., Boulcina, R., Belfaitah, A., Rhouati, S. & Carboni, B. (2008). Synlett, pp. 509-512.  [Web of Science] [CrossRef]
Debache, A., Ghalem, W., Boulcina, R., Belfaitah, A., Rhouati, S. & Carboni, B. (2009). Tetrahedron Lett. 50, 5248-5250.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hoemann, M. Z., Kumaravel, G., Xie, R. L., Rossi, R. F., Meyer, S., Sidhu, A., Cuny, G. D. & Hauske, J. R. (2000). Bioorg. Med. Chem. Lett. 10, 2675-2678.  [CrossRef] [PubMed] [ChemPort]
Jenekhe, S. A., Lu, L. & Alam, M. M. (2001). Macromolecules, 34, 7315-7324.  [CrossRef] [ChemPort]
Nemouchi, S., Boulcina, R., Carboni, B. & Debache, A. (2012). C. R. Chim. 15, 394-397.  [CrossRef] [ChemPort]
Roma, G., Braccio, M. D., Grossi, G., Mattioli, F. & Ghia, M. (2000). Eur. J. Med. Chem. 35, 1021-1035.  [Web of Science] [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, o1719-o1720   [ doi:10.1107/S1600536813029334 ]

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