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Acta Crystallogr Sect E Struct Rep OnlineActa Cryst. EActa Crystallographica Section E: Structure Reports Online1600-5368International Union of Crystallography is267610.1107/S1600536811004922ACSEBHS1600536811004922Organic Papers1,3-Dimethyl-4-phenyl­sulfanyl-1H-pyrazol-5-ol C11H12N2OSShahani Tara aFun Hoong-Kun a*‡Ragavan R. Venkat bVijayakumar V. bSarveswari S. ba X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysiab Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, IndiaCorrespondence e-mail: stephenthomas@example.com‡ Thomson Reuters ResearcherID: A-3561-2009.

01 3 2011 16 2 2011 16 2 2011 67 Pt 3 e110300o633 o633 08 2 2011 09 2 2011 © Shahani et al. 20112011This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.A full version of this article is available from Crystallography Journals Online.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.
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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

Δρmax = 0.33 e Å−3
                        

Δρmin = −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
            

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

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

 Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2676).

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).


Refinement 
The H atoms bound to C atoms were positioned
geometrically (C—H = 0.93–0.96 Å) with Uiso(H) =1.2
or 1.5Ueq(C). The H atoms attached to the N atom
was located from the difference map and refined freely,
[N—H = 0.94 (2) Å].

Figures
Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.

Fig. 2. The crystal structure of the title compound viewed approximately along the b axis. Intermolecular interactions are shown in dashed lines. Hydrogen bond not involved in intermolecular interactions are omitted for clarity.

Crystal data
C11H12N2OS	F(000) = 928	
Mr = 220.30	Dx = 1.328 Mg m−3	
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å	
Hall symbol:  -P 2ac 2ab	Cell parameters from 2873 reflections	
a = 10.9479 (2) Å	θ = 2.8–29.1°	
b = 11.3470 (3) Å	µ = 0.27 mm−1	
c = 17.7392 (4) Å	T = 100 K	
V = 2203.67 (9)  Å3	Block, colourless	
Z = 8	0.33 × 0.13 × 0.11 mm	
Data collection
Bruker SMART APEXII CCD area-detector diffractometer	3027 independent reflections	
Radiation source: fine-focus sealed tube	2406 reflections with I > 2σ(I)	
graphite	Rint = 0.041	
φ and ω scans	θmax = 29.4°, θmin = 2.3°	
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→15	
Tmin = 0.917, Tmax = 0.971	k = −15→15	
12209 measured reflections	l = −16→24	
Refinement
Refinement on F2	Primary atom site location: structure-invariant direct methods	
Least-squares matrix: full	Secondary atom site location: difference Fourier map	
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites	
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement	
S = 1.04	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.8061P]  where P = (Fo2 + 2Fc2)/3	
3027 reflections	(Δ/σ)max < 0.001	
142 parameters	Δρmax = 0.33 e Å−3	
0 restraints	Δρmin = −0.31 e Å−3	
Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra
open-flow nitrogen cryostat (Cosier & Glazer, 1986) stephenthomas@example.com (1) K.	
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.	
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.	
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
	x	y	z	Uiso*/Ueq		
S1	0.09449 (3)	0.31932 (3)	0.09298 (2)	0.01802 (11)		
O1	0.32686 (10)	0.34450 (8)	−0.02532 (6)	0.0207 (2)		
N1	0.20240 (12)	0.61926 (10)	0.00845 (8)	0.0202 (3)		
N2	0.28173 (12)	0.54374 (10)	−0.02791 (7)	0.0192 (3)		
C1	0.28747 (15)	0.36136 (13)	0.19278 (9)	0.0225 (3)		
H1A	0.3057	0.4285	0.1649	0.027*		
C2	0.35663 (15)	0.33304 (13)	0.25590 (9)	0.0254 (3)		
H2A	0.4211	0.3816	0.2700	0.031*		
C3	0.33066 (15)	0.23327 (14)	0.29808 (9)	0.0236 (3)		
H3A	0.3766	0.2154	0.3407	0.028*		
C4	0.23531 (15)	0.16043 (13)	0.27606 (9)	0.0243 (3)		
H4A	0.2180	0.0929	0.3037	0.029*		
C5	0.16551 (14)	0.18758 (13)	0.21304 (9)	0.0212 (3)		
H5A	0.1019	0.1382	0.1986	0.025*		
C6	0.19092 (13)	0.28904 (12)	0.17148 (8)	0.0173 (3)		
C7	0.16428 (13)	0.43840 (11)	0.04922 (8)	0.0166 (3)		
C8	0.26321 (13)	0.43076 (11)	−0.00304 (8)	0.0164 (3)		
C9	0.13144 (14)	0.55679 (12)	0.05474 (8)	0.0178 (3)		
C10	0.38173 (15)	0.58669 (13)	−0.07387 (10)	0.0239 (3)		
H10A	0.4171	0.5222	−0.1013	0.036*		
H10B	0.4427	0.6217	−0.0420	0.036*		
H10C	0.3517	0.6446	−0.1087	0.036*		
C11	0.03683 (15)	0.61354 (14)	0.10271 (9)	0.0248 (3)		
H11A	0.0198	0.6912	0.0839	0.037*		
H11B	0.0661	0.6189	0.1536	0.037*		
H11C	−0.0365	0.5672	0.1016	0.037*		
H1N1	0.1983 (19)	0.700 (2)	−0.0036 (13)	0.047 (6)*		
Atomic displacement parameters (Å2)
	U11	U22	U33	U12	U13	U23	
S1	0.01876 (19)	0.01847 (18)	0.0168 (2)	−0.00372 (13)	−0.00109 (13)	0.00267 (13)	
O1	0.0267 (6)	0.0139 (4)	0.0215 (6)	0.0008 (4)	0.0046 (4)	0.0000 (4)	
N1	0.0264 (7)	0.0129 (5)	0.0212 (7)	0.0017 (5)	−0.0005 (5)	−0.0006 (5)	
N2	0.0240 (6)	0.0131 (5)	0.0206 (7)	−0.0002 (5)	0.0034 (5)	0.0007 (5)	
C1	0.0273 (8)	0.0198 (7)	0.0204 (8)	−0.0046 (6)	−0.0027 (6)	0.0034 (6)	
C2	0.0285 (8)	0.0257 (7)	0.0221 (9)	−0.0037 (6)	−0.0065 (7)	−0.0002 (6)	
C3	0.0255 (8)	0.0298 (8)	0.0155 (8)	0.0053 (6)	−0.0012 (6)	0.0006 (6)	
C4	0.0247 (8)	0.0260 (7)	0.0222 (8)	0.0015 (6)	0.0032 (6)	0.0082 (6)	
C5	0.0197 (7)	0.0213 (7)	0.0225 (8)	−0.0015 (6)	0.0013 (6)	0.0043 (6)	
C6	0.0196 (7)	0.0188 (6)	0.0134 (7)	0.0007 (5)	0.0019 (5)	0.0003 (5)	
C7	0.0193 (7)	0.0148 (6)	0.0156 (7)	−0.0014 (5)	−0.0003 (5)	0.0005 (5)	
C8	0.0224 (7)	0.0127 (6)	0.0141 (7)	−0.0017 (5)	−0.0018 (6)	0.0001 (5)	
C9	0.0207 (7)	0.0179 (6)	0.0149 (7)	0.0009 (5)	−0.0035 (6)	−0.0002 (5)	
C10	0.0283 (8)	0.0184 (7)	0.0250 (8)	−0.0043 (6)	0.0050 (7)	0.0032 (6)	
C11	0.0248 (8)	0.0250 (7)	0.0245 (9)	0.0071 (6)	−0.0008 (6)	−0.0021 (6)	
Geometric parameters (Å, °)
S1—C7	1.7356 (14)	C3—H3A	0.9300	
S1—C6	1.7809 (15)	C4—C5	1.389 (2)	
O1—C8	1.2648 (17)	C4—H4A	0.9300	
N1—C9	1.3343 (19)	C5—C6	1.395 (2)	
N1—N2	1.3801 (17)	C5—H5A	0.9300	
N1—H1N1	0.94 (2)	C7—C9	1.3942 (19)	
N2—C8	1.3708 (17)	C7—C8	1.428 (2)	
N2—C10	1.4494 (19)	C9—C11	1.487 (2)	
C1—C2	1.389 (2)	C10—H10A	0.9600	
C1—C6	1.391 (2)	C10—H10B	0.9600	
C1—H1A	0.9300	C10—H10C	0.9600	
C2—C3	1.387 (2)	C11—H11A	0.9600	
C2—H2A	0.9300	C11—H11B	0.9600	
C3—C4	1.388 (2)	C11—H11C	0.9600	
				
C7—S1—C6	103.83 (7)	C1—C6—S1	123.32 (11)	
C9—N1—N2	108.92 (11)	C5—C6—S1	117.02 (11)	
C9—N1—H1N1	129.0 (13)	C9—C7—C8	107.44 (12)	
N2—N1—H1N1	121.9 (13)	C9—C7—S1	127.24 (12)	
C8—N2—N1	109.70 (12)	C8—C7—S1	125.24 (10)	
C8—N2—C10	127.39 (13)	O1—C8—N2	122.79 (13)	
N1—N2—C10	121.97 (11)	O1—C8—C7	131.88 (13)	
C2—C1—C6	119.79 (14)	N2—C8—C7	105.33 (12)	
C2—C1—H1A	120.1	N1—C9—C7	108.57 (13)	
C6—C1—H1A	120.1	N1—C9—C11	121.85 (13)	
C3—C2—C1	120.80 (15)	C7—C9—C11	129.57 (14)	
C3—C2—H2A	119.6	N2—C10—H10A	109.5	
C1—C2—H2A	119.6	N2—C10—H10B	109.5	
C2—C3—C4	119.26 (15)	H10A—C10—H10B	109.5	
C2—C3—H3A	120.4	N2—C10—H10C	109.5	
C4—C3—H3A	120.4	H10A—C10—H10C	109.5	
C3—C4—C5	120.56 (14)	H10B—C10—H10C	109.5	
C3—C4—H4A	119.7	C9—C11—H11A	109.5	
C5—C4—H4A	119.7	C9—C11—H11B	109.5	
C4—C5—C6	119.92 (14)	H11A—C11—H11B	109.5	
C4—C5—H5A	120.0	C9—C11—H11C	109.5	
C6—C5—H5A	120.0	H11A—C11—H11C	109.5	
C1—C6—C5	119.66 (14)	H11B—C11—H11C	109.5	
				
C9—N1—N2—C8	−1.48 (17)	N1—N2—C8—O1	−177.46 (13)	
C9—N1—N2—C10	−171.15 (14)	C10—N2—C8—O1	−8.5 (2)	
C6—C1—C2—C3	0.0 (2)	N1—N2—C8—C7	2.10 (16)	
C1—C2—C3—C4	0.9 (2)	C10—N2—C8—C7	171.06 (14)	
C2—C3—C4—C5	−0.8 (2)	C9—C7—C8—O1	177.55 (16)	
C3—C4—C5—C6	−0.2 (2)	S1—C7—C8—O1	−5.6 (2)	
C2—C1—C6—C5	−1.0 (2)	C9—C7—C8—N2	−1.96 (16)	
C2—C1—C6—S1	178.43 (12)	S1—C7—C8—N2	174.91 (11)	
C4—C5—C6—C1	1.1 (2)	N2—N1—C9—C7	0.18 (17)	
C4—C5—C6—S1	−178.38 (12)	N2—N1—C9—C11	179.36 (13)	
C7—S1—C6—C1	7.87 (15)	C8—C7—C9—N1	1.12 (17)	
C7—S1—C6—C5	−172.70 (12)	S1—C7—C9—N1	−175.67 (11)	
C6—S1—C7—C9	−100.38 (14)	C8—C7—C9—C11	−177.97 (15)	
C6—S1—C7—C8	83.36 (14)	S1—C7—C9—C11	5.2 (2)	
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	
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x, −y+1/2, z+1/2.

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	
Symmetry codes: (i) ; (ii) .
==== Refs
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