1,3-Dimethyl-4-phenyl­sulfanyl-1H-pyrazol-5-ol

Tara Shahani; Hoong-Kun Fun; R Venkat Ragavan; V Vijayakumar; S Sarveswari

doi:10.1107/S1600536811004922

. 2011 Feb 16;67(Pt 3):o633. doi: 10.1107/S1600536811004922

1,3-Dimethyl-4-phenylsulfanyl-1H-pyrazol-5-ol

Tara Shahani ^a, Hoong-Kun Fun ^a,^*,^‡, R Venkat Ragavan ^b, V Vijayakumar ^b, S Sarveswari ^b

PMCID: PMC3052103 PMID: 21522387

Abstract

In the title compound, C₁₁H₁₂N₂OS, the pyrazole ring makes a dihedral angle of 85.40 (8)° with the phenyl ring. In the crystal, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link molecules into a two-dimensional network parallel to the bc plane.

Related literature

For pyrazole derivatives and their microbial activity, see: Ragavan et al. (2009 ▶, 2010 ▶). For related structures, see: Shahani et al. (2009 ▶, 2010a ▶,b ▶,c ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₁H₁₂N₂OS
M _r = 220.30
Orthorhombic,
a = 10.9479 (2) Å
b = 11.3470 (3) Å
c = 17.7392 (4) Å
V = 2203.67 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.33 × 0.13 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.917, T _max = 0.971
12209 measured reflections
3027 independent reflections
2406 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.104
S = 1.04
3027 reflections
142 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004922/is2676sup1.cif

e-67-0o633-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004922/is2676Isup2.hkl

e-67-0o633-Isup2.hkl^{(148.6KB, 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—H1N1⋯O1ⁱ	0.94 (2)	1.71 (2)	2.6446 (16)	173 (2)
C3—H3A⋯O1ⁱⁱ	0.93	2.53	3.2549 (19)	135

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

Acknowledgments

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship.

supplementary crystallographic information

Comment

Antibacterial and antifungal activities of the azoles are most widely studied and some of them are in clinical practice as anti-microbial agents. However, the azole-resistant strain had led to the development of new antimicrobial compounds. In particular pyrazole derivatives are extensively studied and used as antimicrobial agents. Pyrazole is an important class of heterocyclic compounds and many pyrazole derivatives are reported to have the broad spectrum of biological properties, such as anti-inflammatory, antifungal, herbicidal, anti-tumour, cytotoxic, molecular modelling, and antiviral activities. Pyrazole derivatives also act as antiangiogenic agents, A3 adenosine receptor antagonists, neuropeptide YY5 receptor antagonists, kinase inhibitor for treatment of type 2 diabetes, hyperlipidemia, obesity, and thrombopiotinmimetics. Recently urea derivatives of pyrazoles have been reported as potent inhibitors of p38 kinase. Since the high electronegativity of halogens (particularly chlorine and fluorine) in the aromatic part of the drug molecules play an important role in enhancing their biological activity, we are interested to have 4-fluoro or 4-chloro substitution in the aryls of 1,5-diaryl pyrazoles. As part of our on-going research aiming the synthesis of new antimicrobial compounds, we have reported the synthesis of novel pyrazole derivatives and their microbial activities (Ragavan et al., 2009, 2010). The structure of the title compound is presented here.

In the title compound, (Fig. 1), the 1H-pyrazol ring (C7–C9/N1/N2) [maximum deviation of 0.00117 (14) Å] makes a dihedral angle of 85.40 (8)° with the phenyl ring (C1–C6). The bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to those closely related structures (Shahani et al., 2009, 2010a,b,c).

In the crystal packing (Fig. 2), pairs of intermolecular N1—H1N1···O1 and C3—H3A···O1 hydrogen bonds (Table 1) link the molecules into two-dimensional networks parallel to the bc plane.

Experimental

The compound has been synthesized using the method available in the literature (Ragavan et al., 2009) and recrystallized using the ethanol-chloroform 1:1 mixture (yield 60%, m.p. 444 K).