Ethyl 1-(4-methyl­phen­yl)-5-phenyl-4-phenyl­sulfon­yl-1H-pyrazole-3-carboxyl­ate

Abdel-Aziz, H.A.; Al-Rashood, K.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811036580

Volume 67
Part 10
Pages o2623-o2624
October 2011

Received 7 September 2011
Accepted 8 September 2011
Online 14 September 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.034
wR = 0.091
Data-to-parameter ratio = 14.8
Details

Ethyl 1-(4-methylphenyl)-5-phenyl-4-phenylsulfonyl-1H-pyrazole-3-carboxylate

Hatem A. Abdel-Aziz,^a ⁺ Khalid A. Al-Rashood,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of, Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: Edward.Tiekink@gmail.com

The title compound, C₂₅H₂₂N₂O₄S, features a tetra-substituted pyrazole ring. The dihedral angles formed between the five-membered ring (r.m.s. deviation = 0.007 Å) and the N- and C-bound phenyl rings are 48.10 (7) and 72.01 (7) °, respectively, indicating that the planes through the residues are significantly twisted from the plane through the heterocycle. The ester-CO₂ group is also twisted out of this plane, with an O-C-C-N torsion angle of -29.04 (11)°. The sulfonyl-O atoms lie to one side of the pyrazole plane and the sulfonylphenyl ring to the other. The dihedral angle between the two ring planes is 70.63 (7) °. Supramolecular arrays are formed in the crystal structure sustained by C-HO and C-H [pi] (pyrazole) interactions and methyl-C-H [pi] (N-bound benzene) contacts.

Related literature

For background to the chemistry and biological activity of pyrazole derivatives, see: Abdel-Wahab et al. (2009); Abdel-Aziz et al. (2009, 2010).

Experimental

Crystal data

C₂₅H₂₂N₂O₄S
M_r = 446.51
Triclinic, $[P \overline 1]$
a = 7.2440 (3) Å
b = 11.0798 (5) Å
c = 14.8247 (5) Å
= 68.818 (4)°
= 87.773 (3)°
= 81.241 (4)°
V = 1096.36 (8) Å³
Z = 2
Cu K radiation
= 1.60 mm^-1
T = 100 K
0.40 × 0.30 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010) T_min = 0.566, T_max = 0.740
7378 measured reflections
4304 independent reflections
4106 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.091
S = 0.85
4304 reflections
290 parameters
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1,N2,C4-C6 and C19-C24 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C9-H9O1ⁱ	0.95	2.45	3.2392 (19)	140
C16-H16O2ⁱⁱ	0.95	2.49	3.3928 (18)	158
C17-H17O1ⁱⁱⁱ	0.95	2.50	3.3895 (18)	157
C18-H18O2ⁱⁱⁱ	0.95	2.58	3.4031 (17)	145
C23-H23O4^iv	0.95	2.59	3.3155 (18)	133
C15-H15Cg1ⁱ	0.95	2.80	3.6781 (15)	154
C25-H25cCg2^v	0.98	2.64	3.5649 (16)	157
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y+1, -z; (iii) -x+1, -y+1, -z; (iv) -x+1, -y+1, -z+1; (v) -x+2, -y, -z+1.

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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); 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: BT5639 ).

Acknowledgements

The authors acknowledge the research center, College of Pharmacy, and Deanship of Scientific Research, King Saud University, for financial support of this project. The University of Malaya is also thanked for support of the crystallographic facility.

References

Abdel-Aziz, H. A., El-Zahabi, H. S. A. & Dawood, K. M. (2010). Eur. J. Med. Chem. 45, 2427-2432.
Abdel-Aziz, H. A., Gamal-Eldeen, A. M., Hamdy, N. A. & Fakhr, I. M. I. (2009). Arch. Pharm. 342, 230-237.
Abdel-Wahab, B. F., Abdel-Aziz, H. A. & Ahmed, E. M. (2009). Monatsh. Chem. 140, 601-605.
Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds