5-Pentyl-4-phenyl­sulfonyl-1H-pyrazol-3-ol

Shahani, T.; Fun, H.-K.; Ragavan, R.V.; Vijayakumar, V.; Sarveswari, S.

doi:10.1107/S1600536810019458

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Pages o1482-o1483

https://doi.org/10.1107/S1600536810019458

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5-Pentyl-4-phenylsulfonyl-1H-pyrazol-3-ol

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

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 13 May 2010; accepted 24 May 2010; online 29 May 2010)

In the title compound, C₁₄H₁₈N₂O₃S, 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 intermolecular N—H⋯O and O⋯H⋯N hydrogen bonds form dimers between neighboring molecules, generating R₂²(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 interactions.

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 , 2010a ,b ). 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_r = 294.36
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.122
S = 1.14
7810 reflections
253 parameters
All H-atom parameters refined
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.41 e Å⁻³

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) -x, -y, -z+1; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810019458/wn2386Isup2.hkl

checkCIF report

Comment top

Pyrazolone derivatives have a broad spectrum of biological activities, being used as analgesic, antipyretic and anti-inflammatory therapeutical drugs (Brogden, 1986; Gursoy et al., 2000). A class of new compounds with the pyrazolone unit has been synthesized and reported to possess antibacterial and antifungal activities (Ragavan et al., 2009, 2010). A new pyrazolone derivative, edaravone (3-methyl-1-phenyl-2-pyrazoline-5-one), is being used as a drug in clinical practice for brain ischemia (Watanabe et al., 1984; Kawai et al., 1997) and the same has been found to be effective against myocardial ischemia (Wu et al., 2002).

In the crystal structure (Fig. 1), the 1H-pyrazole ring (C1–C2/N1/N2) is approximately planar, with a maximum deviation of 0.005 (1) Å at atoms C9 and N2. The dihedral angle formed between the 1H-pyrazole and phenyl rings (C1—C6) is 79.09 (5)°. The bond lengths (Allen et al.,1987) and angles are within normal ranges and comparable to those in closely related crystal structures (Shahani et al., 2009, 2010a,b).

In the crystal packing (Fig. 2), pairs of intermolecular O3—H1O3···N1, N2—H1N2···O2 hydrogen bonds form dimers between neighbouring molecules, generating R²₂(8) ring motifs (Bernstein et al., 1995). These dimers are linked into two-dimensional arrays parallel to the ac plane by intermolecular O3—H1O3···N1 and N2—H1N2···O2 hydrogen bonds (Table 1). The crystal structure is also stabilized by C12—H12A···Cg1 interactions (Table 1) involving the C7–C9/N1/N2 pyrazole ring.

Related literature top

For background to the biological activity of 3-ethyl-4-methyl-H-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, 2010a,b). 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 top

The compound 5-pentyl-4-(phenylsulfonyl)-1H-pyrazol-3-ol was synthesized according to the procedure available in the literature (Ragavan et al., 2009, 2010), which in turn was dissolved using a THF/water (1:1) mixture. Oxone (4 mmol) was then added and the solution was stirred at room temperature for 3 h. The reaction mixture was diluted with water (20 ml), and then was extracted with ethyl acetate (2 x 50 ml). The combined extract was washed with water (20 ml) and brine solution (10 ml). Crystallization was carried out using absolute ethanol.

Structure description top

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis, showing 2D arrays parallel to the ac plane. Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

5-Pentyl-4-phenylsulfonyl-1H-pyrazol-3-ol top

Crystal data top

C₁₄H₁₈N₂O₃S	F(000) = 624
M_r = 294.36	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0676P)² + 0.1076P] where P = (F_o² + 2F_c²)/3
7810 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₄H₁₈N₂O₃S	V = 1437.02 (7) Å³
M_r = 294.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.3425 (3) Å	µ = 0.23 mm⁻¹
b = 11.2963 (3) Å	T = 100 K
c = 12.8911 (3) Å	0.48 × 0.33 × 0.11 mm
β = 107.419 (1)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	7810 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6336 reflections with I > 2σ(I)
T_min = 0.896, T_max = 0.976	R_int = 0.035
28969 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.122	All H-atom parameters refined
S = 1.14	Δρ_max = 0.73 e Å⁻³
7810 reflections	Δρ_min = −0.41 e Å⁻³
253 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z+1; (ii) −x, y−1/2, −z+1/2; (iii) x, −y−1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈N₂O₃S
M_r	294.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.3425 (3), 11.2963 (3), 12.8911 (3)
β (°)	107.419 (1)
V (Å³)	1437.02 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.48 × 0.33 × 0.11

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.896, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	28969, 7810, 6336
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.868

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.122, 1.14
No. of reflections	7810
No. of parameters	253
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.41

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x, −y, −z+1; (ii) −x, y−1/2, −z+1/2; (iii) x, −y−1/2, z−3/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

TSH and HKF thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

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Volume 66| Part 6| June 2010| Pages o1482-o1483

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