3-(5-Phenyl-4-phenyl­sulfonyl-1-p-tolyl-1H-pyrazol-3-yl)-1,2-dihydro­quinoxaline

Abdel-Aziz, H.A.; Bari, A.; Ng, S.W.

doi:10.1107/S1600536811005940

Volume 67
Part 3
Page o695
March 2011

Received 14 February 2011
Accepted 17 February 2011
Online 23 February 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.062
wR = 0.158
Data-to-parameter ratio = 13.1
Details

3-(5-Phenyl-4-phenylsulfonyl-1-p-tolyl-1H-pyrazol-3-yl)-1,2-dihydroquinoxaline

Hatem A. Abdel-Aziz,^a Ahmed Bari ^a and Seik Weng Ng ^b ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

In the crystal structure of the title compound, C₃₀H₂₄N₄O₂S, the dihydroquinoxaline fused-ring system is disordered over three orientations in a 0.358 (2):0.318 (3):0.324 (3) ratio; the mean planes of the non-H atoms of the disorder components are aligned at 4.0 (3), 11.8 (4) and 41.7 (2)° with respect to the pyrazole ring. The rings of the phenyl and tolyl substituents are aligned at 64.0 (1) and 43.7 (1)° with respect to the pyrazole ring. Weak intermolecular C-HO hydrogen bonding links the molecules, forming supramolecular chains running along the a axis.

Related literature

For background to the biological properties of aryl-substituted pyrazoles, see: Abdel-Aziz et al. (2010).

Experimental

Crystal data

C₃₀H₂₄N₄O₂S
M_r = 504.59
Monoclinic, P 2₁ /c
a = 6.2829 (2) Å
b = 24.5162 (7) Å
c = 15.9180 (5) Å
= 91.925 (3)°
V = 2450.51 (13) Å³
Z = 4
Mo K radiation
= 0.17 mm^-1
T = 100 K
0.20 × 0.02 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.967, T_max = 0.997
16288 measured reflections
5524 independent reflections
3897 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.158
S = 1.02
5524 reflections
422 parameters
139 restraints
H-atom parameters constrained
_max = 0.38 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C19-H19O1ⁱ	0.95	2.57	3.430 (3)	150
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); 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: XU5163 ).

Acknowledgements

We thank King Saud University and the University of Malaya for supporting this study.

References

Abdel-Aziz, H. A., El-Zahabi, H. S. A. & Dawood, K. M. (2010). Eur. J. Med. Chem. 45, 2427-2432.
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds