5-Pentyl-4-phenyl-sulfonyl-1H-pyrazol-3-ol.

In the title compound, C(14)H(18)N(2)O(3)S, the 1H-pyrazole ring is approximately planar, with a maximum deviation of 0.005 (1) Å. The dihedral angle formed between the 1H-pyrazole and phenyl rings is 79.09 (5)°. Pairs of inter-molecular N-H⋯O and O⋯H⋯N hydrogen bonds form dimers between neighboring mol-ecules, generating R(2) (2)(10) ring motifs. These dimers are further linked by intermolecular N-H⋯O and O-H⋯N hydrogen bonds into two-dimensional arrays parallel to the ac plane. The crystal structure is also stabilized by C-H⋯π inter-actions.

Related literature

For background to the biological activity of 3-ethyl-4-methyl-1H-pyrazol-5-ol, see: Brogden (1986 ▶); Gursoy et al. (2000 ▶); Ragavan et al. (2009 ▶, 2010 ▶); Watanabe et al. (1984 ▶); Kawai et al. (1997 ▶); Wu et al. (2002 ▶). For related structures, see: Shahani et al. (2009 ▶, 2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H18N2O3S

M = 294.36

Monoclinic,

a = 10.3425 (3) Å

b = 11.2963 (3) Å

c = 12.8911 (3) Å

β = 107.419 (1)°

V = 1437.02 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 100 K

0.48 × 0.33 × 0.11 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.896, T max = 0.976

28969 measured reflections

7810 independent reflections

6336 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.122

S = 1.14

7810 reflections

253 parameters

All H-atom parameters refined

Δρmax = 0.73 e Å−3

Δρmin = −0.41 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810019458/wn2386sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019458/wn2386Isup2.hkl

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

C14H18N2O3S	F(000) = 624
Mr = 294.36	Dx = 1.361 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9972 reflections
a = 10.3425 (3) Å	θ = 2.5–37.9°
b = 11.2963 (3) Å	µ = 0.23 mm−1
c = 12.8911 (3) Å	T = 100 K
β = 107.419 (1)°	Plate, colourless
V = 1437.02 (7) Å3	0.48 × 0.33 × 0.11 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	7810 independent reflections
Radiation source: fine-focus sealed tube	6336 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 38.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
Tmin = 0.896, Tmax = 0.976	k = −19→19
28969 measured reflections	l = −22→22

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	All H-atom parameters refined
S = 1.14	w = 1/[σ2(Fo2) + (0.0676P)2 + 0.1076P] where P = (Fo2 + 2Fc2)/3
7810 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq
S1	0.252485 (19)	0.286811 (16)	0.369236 (14)	0.01071 (5)
O1	0.28657 (7)	0.32531 (6)	0.48049 (5)	0.01659 (12)
O2	0.21016 (7)	0.37440 (5)	0.28352 (5)	0.01507 (11)
O3	0.16163 (6)	0.10556 (6)	0.53216 (5)	0.01448 (11)
N1	−0.00782 (8)	0.03707 (6)	0.38100 (6)	0.01404 (12)
N2	−0.04649 (8)	0.06672 (6)	0.27303 (6)	0.01496 (12)
C1	0.40090 (9)	0.19978 (8)	0.24384 (7)	0.01491 (13)
C2	0.50570 (9)	0.13165 (8)	0.22799 (7)	0.01884 (15)
C3	0.59982 (10)	0.07844 (9)	0.31610 (8)	0.02123 (16)
C4	0.59168 (10)	0.09408 (9)	0.42112 (8)	0.02094 (16)
C5	0.48687 (9)	0.16047 (8)	0.43838 (7)	0.01639 (14)
C6	0.39226 (8)	0.21172 (6)	0.34913 (6)	0.01197 (12)
C7	0.09692 (8)	0.10767 (7)	0.42646 (6)	0.01194 (12)
C8	0.12549 (8)	0.18213 (7)	0.34698 (6)	0.01188 (12)
C9	0.02975 (8)	0.15129 (7)	0.24810 (6)	0.01305 (13)
C10	0.00436 (9)	0.19276 (8)	0.13344 (7)	0.01604 (14)
C11	−0.11449 (9)	0.12961 (8)	0.05249 (7)	0.01717 (15)
C12	−0.13109 (9)	0.16318 (8)	−0.06542 (7)	0.01677 (14)
C13	−0.24983 (11)	0.09921 (9)	−0.14480 (7)	0.02131 (17)
C14	−0.25766 (12)	0.11849 (10)	−0.26364 (8)	0.02367 (18)
H1A	0.3342 (16)	0.2363 (14)	0.1852 (12)	0.022 (3)*
H2A	0.5111 (16)	0.1238 (14)	0.1558 (13)	0.025 (4)*
H3A	0.6683 (17)	0.0309 (15)	0.3017 (13)	0.029 (4)*
H4A	0.6624 (17)	0.0595 (14)	0.4792 (13)	0.031 (4)*
H5A	0.4772 (17)	0.1722 (14)	0.5069 (13)	0.026 (4)*
H10A	0.0893 (16)	0.1812 (13)	0.1116 (12)	0.021 (3)*
H10B	−0.0097 (16)	0.2808 (13)	0.1271 (13)	0.022 (4)*
H11A	−0.1995 (16)	0.1492 (13)	0.0666 (12)	0.021 (3)*
H11B	−0.1003 (15)	0.0412 (13)	0.0581 (12)	0.020 (3)*
H12A	−0.1437 (15)	0.2511 (14)	−0.0758 (12)	0.023 (3)*
H12B	−0.0479 (18)	0.1422 (15)	−0.0867 (14)	0.031 (4)*
H13A	−0.2409 (17)	0.0115 (17)	−0.1291 (13)	0.036 (5)*
H13B	−0.3394 (18)	0.1256 (16)	−0.1315 (14)	0.034 (4)*
H14A	−0.2628 (16)	0.2016 (13)	−0.2746 (13)	0.023 (4)*
H14B	−0.3452 (19)	0.0787 (16)	−0.3118 (15)	0.037 (4)*
H14C	−0.1814 (19)	0.0873 (16)	−0.2740 (15)	0.037 (4)*
H1O3	0.1158 (19)	0.0555 (17)	0.5682 (14)	0.042 (5)*
H1N2	−0.1111 (19)	0.0241 (16)	0.2289 (15)	0.039 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.01150 (9)	0.01041 (8)	0.01036 (8)	−0.00003 (5)	0.00348 (6)	0.00008 (5)
O1	0.0196 (3)	0.0179 (3)	0.0126 (2)	−0.0023 (2)	0.0053 (2)	−0.0042 (2)
O2	0.0168 (3)	0.0120 (2)	0.0166 (2)	0.00187 (19)	0.0053 (2)	0.00367 (19)
O3	0.0152 (3)	0.0173 (2)	0.0106 (2)	−0.0011 (2)	0.0033 (2)	0.00243 (18)
N1	0.0157 (3)	0.0151 (3)	0.0112 (2)	−0.0019 (2)	0.0038 (2)	0.0015 (2)
N2	0.0165 (3)	0.0162 (3)	0.0115 (2)	−0.0045 (2)	0.0031 (2)	0.0013 (2)
C1	0.0139 (3)	0.0187 (3)	0.0123 (3)	0.0007 (2)	0.0043 (3)	0.0005 (2)
C2	0.0170 (4)	0.0240 (4)	0.0173 (3)	0.0017 (3)	0.0078 (3)	−0.0014 (3)
C3	0.0164 (4)	0.0244 (4)	0.0240 (4)	0.0054 (3)	0.0078 (3)	0.0012 (3)
C4	0.0168 (4)	0.0251 (4)	0.0200 (4)	0.0075 (3)	0.0043 (3)	0.0050 (3)
C5	0.0152 (3)	0.0198 (3)	0.0134 (3)	0.0034 (3)	0.0032 (3)	0.0031 (3)
C6	0.0108 (3)	0.0131 (3)	0.0119 (3)	0.0000 (2)	0.0032 (2)	0.0010 (2)
C7	0.0128 (3)	0.0122 (3)	0.0114 (3)	0.0008 (2)	0.0043 (2)	0.0006 (2)
C8	0.0123 (3)	0.0123 (3)	0.0112 (3)	−0.0010 (2)	0.0038 (2)	0.0008 (2)
C9	0.0138 (3)	0.0136 (3)	0.0119 (3)	−0.0021 (2)	0.0040 (2)	0.0005 (2)
C10	0.0171 (3)	0.0186 (3)	0.0112 (3)	−0.0048 (3)	0.0025 (3)	0.0019 (2)
C11	0.0181 (4)	0.0196 (3)	0.0126 (3)	−0.0052 (3)	0.0026 (3)	0.0008 (3)
C12	0.0183 (4)	0.0184 (3)	0.0127 (3)	−0.0032 (3)	0.0033 (3)	0.0012 (2)
C13	0.0239 (4)	0.0243 (4)	0.0132 (3)	−0.0059 (3)	0.0016 (3)	0.0004 (3)
C14	0.0290 (5)	0.0268 (4)	0.0134 (3)	0.0016 (4)	0.0037 (3)	0.0000 (3)

S1—O1	1.4379 (6)	C5—H5A	0.928 (16)
S1—O2	1.4498 (6)	C7—C8	1.4233 (11)
S1—C8	1.7263 (8)	C8—C9	1.4039 (11)
S1—C6	1.7610 (8)	C9—C10	1.4969 (11)
O3—C7	1.3264 (10)	C10—C11	1.5300 (12)
O3—H1O3	0.944 (19)	C10—H10A	1.009 (15)
N1—C7	1.3315 (11)	C10—H10B	1.004 (15)
N1—N2	1.3697 (10)	C11—C12	1.5255 (12)
N2—C9	1.3377 (10)	C11—H11A	0.976 (16)
N2—H1N2	0.880 (18)	C11—H11B	1.009 (14)
C1—C6	1.3932 (11)	C12—C13	1.5248 (13)
C1—C2	1.3934 (12)	C12—H12A	1.005 (16)
C1—H1A	0.952 (15)	C12—H12B	1.006 (17)
C2—C3	1.3917 (14)	C13—C14	1.5254 (13)
C2—H2A	0.952 (16)	C13—H13A	1.010 (19)
C3—C4	1.3926 (14)	C13—H13B	1.035 (18)
C3—H3A	0.950 (17)	C14—H14A	0.949 (15)
C4—C5	1.3897 (13)	C14—H14B	1.034 (18)
C4—H4A	0.959 (16)	C14—H14C	0.910 (19)
C5—C6	1.3937 (11)
O1—S1—O2	118.80 (4)	C7—C8—S1	126.64 (6)
O1—S1—C8	108.67 (4)	N2—C9—C8	105.38 (7)
O2—S1—C8	107.44 (4)	N2—C9—C10	121.26 (7)
O1—S1—C6	109.00 (4)	C8—C9—C10	133.35 (7)
O2—S1—C6	106.88 (4)	C9—C10—C11	113.28 (7)
C8—S1—C6	105.24 (4)	C9—C10—H10A	109.0 (8)
C7—O3—H1O3	110.0 (11)	C11—C10—H10A	109.8 (8)
C7—N1—N2	104.62 (6)	C9—C10—H10B	111.6 (9)
C9—N2—N1	113.89 (7)	C11—C10—H10B	109.8 (9)
C9—N2—H1N2	128.6 (12)	H10A—C10—H10B	102.9 (12)
N1—N2—H1N2	117.2 (12)	C12—C11—C10	113.05 (7)
C6—C1—C2	118.42 (8)	C12—C11—H11A	106.9 (9)
C6—C1—H1A	119.3 (9)	C10—C11—H11A	110.6 (9)
C2—C1—H1A	122.2 (9)	C12—C11—H11B	106.7 (8)
C3—C2—C1	120.24 (8)	C10—C11—H11B	110.1 (8)
C3—C2—H2A	121.7 (10)	H11A—C11—H11B	109.4 (12)
C1—C2—H2A	118.0 (10)	C13—C12—C11	112.25 (7)
C2—C3—C4	120.50 (9)	C13—C12—H12A	109.4 (9)
C2—C3—H3A	117.7 (10)	C11—C12—H12A	110.5 (8)
C4—C3—H3A	121.8 (10)	C13—C12—H12B	106.7 (10)
C5—C4—C3	120.07 (8)	C11—C12—H12B	111.3 (10)
C5—C4—H4A	122.9 (10)	H12A—C12—H12B	106.5 (13)
C3—C4—H4A	117.0 (10)	C12—C13—C14	113.34 (8)
C4—C5—C6	118.72 (8)	C12—C13—H13A	108.9 (10)
C4—C5—H5A	122.7 (10)	C14—C13—H13A	108.4 (9)
C6—C5—H5A	118.5 (10)	C12—C13—H13B	109.5 (10)
C1—C6—C5	122.01 (8)	C14—C13—H13B	110.1 (10)
C1—C6—S1	119.01 (6)	H13A—C13—H13B	106.4 (13)
C5—C6—S1	118.88 (6)	C13—C14—H14A	106.0 (9)
O3—C7—N1	122.36 (7)	C13—C14—H14B	108.3 (10)
O3—C7—C8	126.91 (7)	H14A—C14—H14B	109.9 (14)
N1—C7—C8	110.73 (7)	C13—C14—H14C	107.7 (11)
C9—C8—C7	105.37 (7)	H14A—C14—H14C	112.0 (15)
C9—C8—S1	127.99 (6)	H14B—C14—H14C	112.7 (15)
C7—N1—N2—C9	0.83 (10)	O3—C7—C8—S1	0.59 (12)
C6—C1—C2—C3	−0.77 (14)	N1—C7—C8—S1	−179.79 (6)
C1—C2—C3—C4	−0.99 (15)	O1—S1—C8—C9	155.48 (7)
C2—C3—C4—C5	1.82 (16)	O2—S1—C8—C9	25.76 (9)
C3—C4—C5—C6	−0.84 (14)	C6—S1—C8—C9	−87.89 (8)
C2—C1—C6—C5	1.76 (13)	O1—S1—C8—C7	−25.08 (8)
C2—C1—C6—S1	−174.63 (7)	O2—S1—C8—C7	−154.80 (7)
C4—C5—C6—C1	−0.96 (13)	C6—S1—C8—C7	91.55 (8)
C4—C5—C6—S1	175.44 (7)	N1—N2—C9—C8	−0.98 (10)
O1—S1—C6—C1	−159.60 (6)	N1—N2—C9—C10	178.47 (7)
O2—S1—C6—C1	−30.03 (7)	C7—C8—C9—N2	0.71 (9)
C8—S1—C6—C1	84.00 (7)	S1—C8—C9—N2	−179.75 (6)
O1—S1—C6—C5	23.90 (8)	C7—C8—C9—C10	−178.65 (9)
O2—S1—C6—C5	153.46 (7)	S1—C8—C9—C10	0.89 (14)
C8—S1—C6—C5	−92.50 (7)	N2—C9—C10—C11	0.26 (12)
N2—N1—C7—O3	179.32 (7)	C8—C9—C10—C11	179.54 (9)
N2—N1—C7—C8	−0.31 (9)	C9—C10—C11—C12	−174.25 (8)
O3—C7—C8—C9	−179.86 (8)	C10—C11—C12—C13	179.91 (8)
N1—C7—C8—C9	−0.25 (9)	C11—C12—C13—C14	−172.45 (8)

Cg1 is the centroid of the 1H-pyrazole ring (C7–C9/N1/N2).

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N1i	0.945 (19)	1.79 (2)	2.7287 (10)	171.5 (17)
N2—H1N2···O2ii	0.880 (19)	1.959 (19)	2.7162 (10)	143.4 (17)
C12—H12A···Cg1iii	1.005 (16)	2.952 (16)	3.5692 (10)	120.5 (11)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the 1H-pyrazole ring (C7–C9/N1/N2).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯N1i	0.945 (19)	1.79 (2)	2.7287 (10)	171.5 (17)
N2—H1N2⋯O2ii	0.880 (19)	1.959 (19)	2.7162 (10)	143.4 (17)
C12—H12A⋯Cg1iii	1.005 (16)	2.952 (16)	3.5692 (10)	120.5 (11)

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