5-Methyl-1-[(4-methyl­phen­yl)sulfon­yl]-1H-pyrazol-3-yl 4-methyl­benzene­sulfonate

Shahzad Murtaza; Naghmana Kausar; M Nawaz Tahir; Javaria Tariq; Samaira Bibi

doi:10.1107/S1600536812027717

. 2012 Jun 23;68(Pt 7):o2196. doi: 10.1107/S1600536812027717

5-Methyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrazol-3-yl 4-methylbenzenesulfonate

Shahzad Murtaza ^a, Naghmana Kausar ^a, M Nawaz Tahir ^b,^*, Javaria Tariq ^a, Samaira Bibi ^a

PMCID: PMC3393995 PMID: 22798860

Abstract

In the title compound, C₁₈H₁₈N₂O₅S₂, the tolyl rings are oriented at a dihedral angle of 16.15 (11)° with respect to one another. The 5-methyl-1H-pyrazol-3-ol ring is roughly planar (r.m.s. deviation = 0.0231 Å) and subtends angles of 73.82 (8) and 89.85 (8)° with the tolyl rings. In the crystal, very weak π–π interactions between tolyl groups, with centroid–centroid distances of 4.1364 (19) and 4.0630 (16) Å, together with a C—H⋯π contact generate a three-dimensional network.

Related literature

For related structures, see: Gogoi et al. (2009 ▶); Murtaza et al. (2012 ▶).

Experimental

Crystal data

C₁₈H₁₈N₂O₅S₂
M _r = 406.46
Monoclinic,
a = 22.296 (2) Å
b = 8.0444 (7) Å
c = 20.915 (2) Å
β = 98.521 (6)°
V = 3709.7 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 296 K
0.30 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.910, T _max = 0.933
15506 measured reflections
4124 independent reflections
2548 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.128
S = 1.01
4124 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027717/sj5243sup1.cif

e-68-o2196-sup1.cif^{(27.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027717/sj5243Isup2.hkl

e-68-o2196-Isup2.hkl^{(198.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812027717/sj5243Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18b⋯Cg2ⁱ	0.96	2.66	3.471 (3)	142

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, former Vice Chancellor of the University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

supplementary crystallographic information

Comment

The title compound (I), (Fig. 1) has been synthesized as part of a study of enzyme inhibition and other biological activities of molecules incoorporating pyrazole moiety, an important component of many drugs. (I), was also prepared as a continuation of our work on sulfonyl derivatives, such as ethyl (3E)-3-[2-(4-bromophenylsulfonyl)hydrazin-1-ylidene]butanoate (Murtaza et al., 2012). The crystal structure of 1(R)-4-(3-hydroxy-5-methyl-pyrazol-1-yl)-octan-2-one (Gogoi et al. 2009) has also been published and contains a 5-methyl-1H-pyrazol-3-ol unit similar to the one observed here.

In (I) , Fig. 1, the tolyl groups A (C1—C7) and B (C12—C18) are planar with r.m.s. deviations of 0.0137 and 0.0043 Å, respectively. The dihedral angle between the A/B planes is 16.15 (11)°. The central group, 5-methyl-1H-pyrazol-3-ol, C (C8—C11/N1/N2/O3) is also planar with an r.m.s. deviation of 0.0231 Å. The sulfonyl groups D (O1/S1/O2) and E (O4/S2/O5) are of course planar. The dihedral angles between A/C, A/D, A/E, B/C, B/D and B/E are 89.85 (8)°, 43.20 (9)°, 67.25 (13)°, 73.82 (8)°, 31.56 (9)° and 33.61 (12)°, respectively.

C18—H18b···π contacts form between dissimilar tolyl rings (Table 1). Weak π–π interactions are also found between like ring systems Cg2···Cg2ⁱ [i = 1/2 - x, 1/2 - y, 1 - z] and Cg3···Cg3ⁱⁱ [ii = - x, y, 1/2 - z] at distances of 4.1364 (19) and 4.0630 (16) %A respectively, where Cg2 and Cg3 are the centroids of the (C1—C6) and (C12—C17), benzene rings. These interactions play a role in stabilizing the structure, generating a three dimensional network.

Experimental

A solution of 3-methyl-1H-pyrazol-5-ol (0.1 g, 1 mmol) was prepared in anhydrous tetrahydrofuran (THF) and NaH (0.048 g, 2 mmol) was added to it at room temperature. A separately prepared solution of 4-methyl benzenesulfonyl chloride (0.19 g, 0.001 mol) in THF (10 ml) was added dropwise to the above mixture. The mixture was stirred for 2 h and solvent was evaporated to yield white prisms of (I).

M. p. 483 K.