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Volume 69 
Part 10 
Page o1582  
October 2013  

Received 11 June 2013
Accepted 17 September 2013
Online 25 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
R = 0.047
wR = 0.120
Data-to-parameter ratio = 13.0
Details
Open access

N-(4-Acetyl-3-methyl-1-phenyl-1H-pyrazol-5-yl)-N-methyl-2-(2-methyl-4-oxo-3,4-dihydroquinazolin-3-yl)benzamide

aDepartment of Pharmaceutical Sciences, University of Milano, via L. Mangiagalli, 25, 20133-Milano, Italy, and bDipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche, University of Palermo, via Archirafi, 32, 90123-Palermo, Italy
Correspondence e-mail: fiorella.meneghetti@unimi.it

In the title compound, C29H25N5O3, the dihedral angle between the benzene ring and the pendant quinazoline ring system (r.m.s. deviation = 0.036Å) is 87.60 (17)°. The equivalent angle between the pyrazole ring and the phenyl group is 70.0 (2)°. The dihedral angle between the benzene and pyrazole rings is 30.7 (2)° and overall, the molecular conformation approximates to a Z shape. A short intramolecular C-H...O contact occurs. In the crystal, the molecules are linked by C[pi]-H...O-type hydrogen bonds and aromatic [pi]-[pi] stacking interactions [centroid-centroid distance = 3.860 (3) Å], generating a three-dimensional network.

Related literature

For background to the bioactivity of methaqualone and its derivatives, see: Ionescu-Pioggia et al. (1988)[Ionescu-Pioggia, M., Bird, M., Orzaci, M. H., Benes, F., Beake, B. & Cole, J. O. (1988). Int. Clin. Psyco. Pharmacol. 3, 97-109.]; Wolfe et al. (1990[Wolfe, J. F., Rathman, T. L., Sleevi, M. C., Campbell, J. A. & Greenwood, T. D. (1990). J. Med. Chem. 33, 161-166.]). For structural and molecular modeling studies of quinazolinone derivatives, see: Duke & Codding (1993[Duke, N. E. C. & Codding, P. W. (1993). Acta Cryst. B49, 719-726.]). For further synthetic details, see: Plescia et al. (1978[Plescia, S., Daidone, G., Sprio, V., Aiello, E., Dattolo, G. & Cirrincione, G. (1978). J. Heterocycl. Chem. 15, 1339-1342.]).

[Scheme 1]

Experimental

Crystal data
  • C29H25N5O3

  • Mr = 491.54

  • Monoclinic, P 21 /c

  • a = 8.617 (4) Å

  • b = 20.438 (5) Å

  • c = 15.038 (5) Å

  • [beta] = 106.27 (2)°

  • V = 2542.3 (16) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.6 × 0.5 × 0.4 mm

Data collection
  • Enraf-Nonius TurboCAD-4 diffractometer

  • 5236 measured reflections

  • 4401 independent reflections

  • 1358 reflections with I > 2[sigma](I)

  • Rint = 0.062

  • 3 standard reflections every 120 min intensity decay: -3%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.120

  • S = 0.92

  • 4401 reflections

  • 338 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 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
C21-H21C...O1 0.96 2.57 3.214 (5) 124
C3-H3...O2i 0.93 2.54 3.351 (6) 146
C5-H5...O1ii 0.93 2.40 3.276 (5) 157
C16-H16...O3iii 0.93 2.52 3.305 (6) 143
Symmetry codes: (i) x+1, y, z; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); 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.]); software used to prepare material for publication: WinGX publication routines (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: HB7092 ).


Acknowledgements

Financial support from the Fondo di Finanziamento della Ricerca - ex 60%, University of Palermo, is gratefully acknowledged.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [IUCr Journals]
Duke, N. E. C. & Codding, P. W. (1993). Acta Cryst. B49, 719-726.  [CSD] [CrossRef] [IUCr Journals]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Ionescu-Pioggia, M., Bird, M., Orzaci, M. H., Benes, F., Beake, B. & Cole, J. O. (1988). Int. Clin. Psyco. Pharmacol. 3, 97-109.  [ChemPort]
Plescia, S., Daidone, G., Sprio, V., Aiello, E., Dattolo, G. & Cirrincione, G. (1978). J. Heterocycl. Chem. 15, 1339-1342.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wolfe, J. F., Rathman, T. L., Sleevi, M. C., Campbell, J. A. & Greenwood, T. D. (1990). J. Med. Chem. 33, 161-166.  [CrossRef] [ChemPort] [PubMed] [Web of Science]


Acta Cryst (2013). E69, o1582  [ doi:10.1107/S1600536813025683 ]

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