(E,E)-4-{4-[3-(4-Chloro­anilino)-1-hydroxy­but-2-enyl­idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}­benzene­sulfonamide

Abdullah M Asiri; Hassan M Faidallah; Seik Weng Ng

doi:10.1107/S1600536811020617

. 2011 Jun 4;67(Pt 7):o1590. doi: 10.1107/S1600536811020617

(E,E)-4-{4-[3-(4-Chloroanilino)-1-hydroxybut-2-enylidene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}benzenesulfonamide

Abdullah M Asiri ^a, Hassan M Faidallah ^a, Seik Weng Ng ^b,^*

PMCID: PMC3151870 PMID: 21836998

Abstract

The molecule of the title compound, C₂₀H₁₉ClN₄O₄S, features a central pyrazole ring that possesses a benzene substituent, as well as a conjugated =C—C=C—C_methyl substituent. The benzene ring is slightly twisted [dihedral angle = 7.7 (2)°] with respect to the five-membered ring; the mean plane of the zigzag =C—C=C—C fragment [torsion angle = 178.0 (4)°] is also slightly twisted [dihedral angle = 10.6 (4)°]. The amine and hydroxy groups form intramolecular hydrogen bonds. The amide group uses one of its H atoms to form a hydrogen bond to the sulfamyl O atom of an inversion-related molecule. Adjacent dimers are further linked by an N—H_amido⋯N_pyrazole hydrogen bond to generate a linear chain. The crystal studied is a nonmerohedral twin with a minor twin component of 25.6 (2)%.

Related literature

For the synthesis of 4-acetoacetyl-3-methyl-5-onyl-1-phenylpyrazole, see: Gelin et al. (1983 ▶).

Experimental

Crystal data

C₂₀H₁₉ClN₄O₄S
M _r = 446.90
Monoclinic,
a = 14.7513 (17) Å
b = 17.545 (2) Å
c = 7.6203 (9) Å
β = 101.496 (2)°
V = 1932.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 100 K
0.20 × 0.02 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (TWINABS; Bruker, 2009 ▶) T _min = 0.935, T _max = 0.993
32586 measured reflections
3426 independent reflections
2605 reflections with I > 2σ(I)
R _int = 0.099

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.125
S = 1.04
3426 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020617/xu5227sup1.cif

e-67-o1590-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020617/xu5227Isup2.hkl

e-67-o1590-Isup2.hkl^{(168KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811020617/xu5227Isup3.cml

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
O1—H1O⋯O2	0.84	1.79	2.498 (4)	141
N1—H1⋯O1	0.88	2.00	2.659 (4)	131
N1—H1⋯O3ⁱ	0.88	2.34	3.093 (4)	143
N4—H41⋯N2ⁱⁱ	0.88	2.16	3.003 (4)	161
N4—H42⋯O4ⁱⁱⁱ	0.88	2.09	2.917 (4)	156

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

Acknowledgments

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The compound, 4-acetoacetyl-3-methyl-5-onyl-1-phenylpyrazole rearranges under the influence of acetic acid to form functionalized 4-oxopyrano[2,3-c]pyrazoles (Gelin et al., 1983). The addition of a sulfamido unit to the phenyl ring is expected to improve its biological activity; in the present study, the p-sulfamyl analog is reacted with chloroaniline to yield a new p-sulfamylphenylpyrazole derivative (Scheme I). The C₂₀H₁₉ClN₄O₄S (Fig. 1) features a central pyrazole ring that possesses a benzene substituent as well as a conjugated ═ C–C═C–C_methyl substituent. The benzene ring is slightly twisted with respect to the five-membered ring; the mean plane of the zigzag ═ C–C═ C–C fragment is also slightly twisted.

The amino and hydroxy groups are intramolecular hydrogen-bond donors. The amido group uses one of its H atoms to form an hydrogen bond to the sulfamyl O atom of an inversion-related molecule. Adjacent dimers are further linked by an N–H_amido···N_pyrazole hydrogen bond to generate a linear chain motif (Table 2, Fig. 2).

Experimental

4-Acetoacetyl-3-methyl-5-onyl-1-p-sulfamylphenylpyrazole was synthesized by using a literature procedure (Gelin et al., 1983). The compound (1.70 g, 0.005 mol) and 4-chloroaniline (0.63 g, 0.005 mol) were heated in ethanol (25 ml) for 2 h. The solid that separated from solution was collected and recrystallized from ethanol to yield yellow prismatic crystals.