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Volume 69 
Part 8 
Pages o1320-o1321  
August 2013  

Received 16 July 2013
Accepted 19 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.117
Data-to-parameter ratio = 18.7
Details
Open access

N'-Phenyl-N'-[3-(2,4,5-triphenyl-2,5-dihydro-1H-pyrazol-3-yl)quinoxalin-2-yl]benzohydrazide

aLaboratoire National de Contrôle des Médicaments, D M P, Ministère de la Santé, Madinat Al Irnane, BP 6206, Rabat, Morocco,bLaboratoire de Chimie Thérapeutique, Faculté de Médecine et de Pharmacie de Rabat-Souissi, Université Mohamed V, BP 6203, Rabat, Morocco,cLaboratoire de Chimie Organique Hétérocyclique URAC21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco,dInstitute of Nanomaterials and Nanotechnology, MASCIR, Rabat, Morocco, and eLaboratoire de Chimie du Solide Appliquée, Université Mohammed V-Agdal, Faculté des Sciences, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: k_karrouchi@yahoo.fr

The molecule of the title compound, C42H32N6O, is built up from one pyrazole ring linked to three phenyl rings and to an approximately planar [maximum deviation = 0.0455 (15) Å] quinoxaline system connected to a phenylbenzohydrazide group. The pyrazole ring assumes an envelope conformation, the C atom attached to the quinoxalin-3-yl ring system being the flap atom. The dihedral angle between the two phenyl rings of the phenylbenzohydrazide group is of 58.27 (9)°. The mean plane through the pyrazole ring is nearly perpendicular to the quinoxaline ring system and to the phenyl ring attached to the opposite side, forming dihedral angles of 82.58 (7) and 87.29 (9)°, respectively. An intramolecular C-H...O hydrogen bond is present. In the crystal, molecules are linked by pairs of N-H...N hydrogen bonds, forming inversion dimers, which are further connected by C-H...N hydrogen bonds into chains parallel to the b axis.

Related literature

For the biological activity of quinoxaline derivatives, see: El-Sabbagh et al. (2009[El-Sabbagh, O. I., El-Sadek, M. E., Lashine, S. M., Yassin, S. H. & El-Nabtity, S. M. (2009). Med. Chem. Res. 18 9, 782-797.]); Bemis & Duffy (2005[Bemis, G. W. & Duffy, J. P. (2005). Patent WO 2005/056547 A2.]); Corona et al. (2008[Corona, P., Carta, A., Loriga, M., Vitale, G. & Paglietti, G. (2008). Eur. J. Med. Chem. 44, 1579-1591.]); Ghadage & Shirote (2011[Ghadage, R. V. & Shirote, P. J. (2011). J. Chem. Pharm. Res. 3, 260-266.]); Yang et al. (2012[Yang, Y., Zhang, S., Wu, B., Ma, M., Chen, X., Qin, X., He, M., Hussain, S., Jing, C., Ma, B. & Zhu, C. (2012). ChemMedChem, 7, 823-835.]).

[Scheme 1]

Experimental

Crystal data
  • C42H32N6O

  • Mr = 636.74

  • Monoclinic, P 21 /n

  • a = 12.0127 (3) Å

  • b = 19.4679 (5) Å

  • c = 15.2083 (4) Å

  • [beta] = 106.045 (1)°

  • V = 3418.09 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.41 × 0.32 × 0.21 mm

Data collection
  • Bruker X8 APEXII area-detector diffractometer

  • 39727 measured reflections

  • 8306 independent reflections

  • 4919 reflections with I > 2[sigma](I)

  • Rint = 0.050

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

  • wR(F2) = 0.117

  • S = 1.00

  • 8306 reflections

  • 443 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O3 0.98 2.28 3.2425 (19) 169
N6-H6N...N4i 0.89 2.30 3.1754 (18) 172
C16-H16...N2ii 0.93 2.56 3.4799 (19) 172
Symmetry codes: (i) -x, -y, -z+1; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5080 ).


Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Bemis, G. W. & Duffy, J. P. (2005). Patent WO 2005/056547 A2.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Corona, P., Carta, A., Loriga, M., Vitale, G. & Paglietti, G. (2008). Eur. J. Med. Chem. 44, 1579-1591.  [CrossRef] [PubMed]
El-Sabbagh, O. I., El-Sadek, M. E., Lashine, S. M., Yassin, S. H. & El-Nabtity, S. M. (2009). Med. Chem. Res. 18 9, 782-797.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ghadage, R. V. & Shirote, P. J. (2011). J. Chem. Pharm. Res. 3, 260-266.  [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]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Yang, Y., Zhang, S., Wu, B., Ma, M., Chen, X., Qin, X., He, M., Hussain, S., Jing, C., Ma, B. & Zhu, C. (2012). ChemMedChem, 7, 823-835.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1320-o1321   [ doi:10.1107/S1600536813020035 ]

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