N′-(3-Methyl­quinoxalin-2-yl)-N′-phenyl­benzohydrazide

Ramli, Y.; Moussaif, A.; Zouihri, H.; Bourichi, H.; Essassi, E.M.

doi:10.1107/S160053681101703X

Volume 67
Part 6
Page o1374
June 2011

Received 21 April 2011
Accepted 5 May 2011
Online 11 May 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.130
Data-to-parameter ratio = 18.4
Details

N'-(3-Methylquinoxalin-2-yl)-N'-phenylbenzohydrazide

Youssef Ramli,^a,^b ^* Ahmed Moussaif,^c Hafid Zouihri,^d Houda Bourichi ^b and El Mokhtar Essassi ^b

^aLaboratoire Nationale de Controle des Médicaments, Direction du Médicament et de la Pharmacie, BP 6206, 10000 Rabat, Morocco,^bLaboratoire de Chimie Hétérocyclique, Pole de Compétence PHARCHIM, Université Mohammed V-Agdal, BP 1014, Rabat, Morocco,^cUnité de la Radioimmunoanalyse, Centre National d'Etudes Scientifiques et Techniques d'Energie Nucléaire, Maamoura, Morocco, and ^dLaboratoire de Diffraction des Rayons X, Division UATRS, Centre National pour la Recherche Scientifique et Technique, Rabat, Morocco
Correspondence e-mail: yramli76@yahoo.fr

In the crystal structure of the title compound, C₂₂H₁₈N₄O, the quinoxaline system makes dihedral angles of 86.59 (7) and 63.37 (9)° with the benzohydrazide and phenyl rings, respectively. The benzohydrazide ring makes a dihedral angle of 72.46 (10)° with the phenyl ring. The crystal structure is stabilized by intermolecular N-HO hydrogen bonds, C-HO contacts and C-H [pi] interactions.

Related literature

For the biological activity of quinoxaline derivatives, see: Kleim et al. (1995). For the antitumour and antituberculous properties of quinoxaline derivatives, see: Abasolo et al. (1987); Rodrigo et al. (2002). For interesting antifungal, herbicidal, antidyslipidemic and antioxidative activities of quinoxaline derivatives, see: Jampilek et al. (2005); Sashidhara et al. (2009); Watkins et al. (2009).

Experimental

Crystal data

C₂₂H₁₈N₄O
M_r = 354.40
Monoclinic, P 2₁ /c
a = 18.6809 (12) Å
b = 10.5840 (8) Å
c = 9.5860 (6) Å
= 100.108 (3)°
V = 1865.9 (2) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 296 K
0.35 × 0.34 × 0.18 mm

Data collection

Bruker APEXII CCD detector diffractometer
19397 measured reflections
4502 independent reflections
2286 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.130
S = 1.01
4502 reflections
245 parameters
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C8-C13 rings, respectively.

D-HA	D-H	HA	DA	D-HA
N4-H6O1ⁱ	0.86	2.05	2.863 (2)	157
C18-H18O1ⁱⁱ	0.93	2.57	3.496 (3)	175
C22-H22BCg1ⁱⁱⁱ	0.96	2.99	3.696 (2)	131
C20-H20Cg2^iv	0.93	2.94	3.866 (2)	175
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (iv) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5532 ).

Acknowledgements

The authors thank the CNRST, Morocco, for making this work possible.

References

Abasolo, M. I., Gaozza, C. H. & Fernandez, B. M. (1987). J. Heterocycl. Chem. 24, 1771-1775.
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Jampilek, J., Dolezal, M., Kunes, J., Buchta, V. & Kralova, K. (2005). Med. Chem. 1, 591-599.
Kleim, J. P., Bender, R., Kirsch, R., Meichsner, C., Paessens, A., Rosner, M., Rubsamen Waigmann, H., Kaiser, R., Wichers, M., Schneweis, K. E., Winkler, I. & Riess, G. (1995). Antimicrob. Agents Chemother. 39, 2253-2257.
Rodrigo, G. A., Robinshon, A. E., Hedrera, M. E., Kogan, M., Sicardi, S. M. & Fernaandez, B. M. (2002). Trends Heterocycl. Chem. 8, 137-143.
Sashidhara, K. V., Kumar, A., Bhatia, G., Khan, M. M., Khanna, A. K. & Saxena, J. K. (2009). Eur. J. Med. Chem. 44, 1813-1818.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Watkins, A. J., Nicol, G. W. & Shawa, L. J. (2009). Soil Biol. Biochem. 41, 580-585.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds