N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-4-methyl­benzene­sulfonamide

Luiz Everson da Silva; Paulo Teixeira de Sousa Jr; Evandro Luiz Dall’Oglio; Sabine Foro

doi:10.1107/S1600536807061594

. 2007 Dec 6;64(Pt 1):o52. doi: 10.1107/S1600536807061594

N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-4-methylbenzenesulfonamide

Luiz Everson da Silva ^a, Paulo Teixeira de Sousa Jr ^a, Evandro Luiz Dall’Oglio ^a, Sabine Foro ^b,^*

PMCID: PMC2915010 PMID: 21200928

Abstract

In the title compound, C₁₈H₁₉N₃O₃S, the phenyl ring and the pyrazole ring are twisted with respect to each other by an angle of 49.11 (7)°. The C—N—S—C torsion angle is −122.5 (2)°. The methyl group bonded to the N atom of the pyrazole ring has a large deviation from the mean ring plane of 0.603 (3) Å. One intermolecular N—H⋯O and two non-classical intermolecular C—H⋯O hydrogen bonds are observed in the crystal structure.

Related literature

For related literature, see: Xue et al. (2000 ▶); Alves & Duarte (2002 ▶).

Experimental

Crystal data

C₁₈H₁₉N₃O₃S
M _r = 357.42
Triclinic,
a = 9.202 (1) Å
b = 9.892 (1) Å
c = 10.067 (1) Å
α = 103.688 (9)°
β = 90.360 (9)°
γ = 104.300 (9)°
V = 860.71 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 299 (2) K
0.50 × 0.20 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.902, T _max = 0.967
10096 measured reflections
3519 independent reflections
2600 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.109
S = 1.07
3519 reflections
259 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXS97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807061594/bt2634sup1.cif

e-64-00o52-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061594/bt2634Isup2.hkl

e-64-00o52-Isup2.hkl^{(172.5KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3ⁱ	0.87 (2)	1.97 (2)	2.826 (2)	167.1 (18)
C2—H2⋯O1ⁱⁱ	0.92 (2)	2.54 (2)	3.270 (2)	136.4 (16)
C12—H12⋯O2ⁱⁱⁱ	0.97 (2)	2.43 (2)	3.245 (2)	141.9 (17)

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors thank Professor Dr. Hartmut Fuess, Technische Universität Darmstadt, for diffractometer time.

supplementary crystallographic information

Comment

Pyrazolone derivatives, as dypirone, known as a non-steroidal anti-inflammatory drug show analgesic property and have been widely used in Europa and Latin America (Alves & Duarte, 2002). The crystal elucidation of the title compound is a strategy to find new 4-aminoantypirine derivatives with biological significance.

The pyrazole moiety forms a C8—N1—S1—C1 torsion angle with the toluene ring of -122.5 (2)° and a dihedral angle between the mean planes of 49.11 (7)° with the phenyl ring showing the nonplanarity of the system. The methyl group with C18 bounded to the nitrogen atom N2 of the pyrazole ring has a high deviation from the mean plane of -0.603 (3) Å. The NH group has an intermolecular hydrogen bond to the oxygen atom O3 [N—H···O = 1.97 (2) Å]. Both sulfonamide oxygen atoms O1 and O2 are involved in non-classical intermolecular hydrogen bonds with C2 and C12 [C—H···O = 2.54 (2) Å, C—H···O = 2.43 (2) Å, respectively] (Table 1).

Experimental

The ligand was obtained according to the procedure previously described (Xue et al., 2000). Single crystals of (I) suitable for X-ray data collection appeared after a few days from methanol-dichloromethane (1:1).