4-(5,3′-Dimethyl-5′-oxo-2-phenyl-2′,5′-dihydro-2H-[3,4′]bipyrazol-1′-yl)benzene­sulfonamide monohydrate

Abdullah M Asiri; Abdulrahman O Al-Youbi; Hassan M Faidallah; Khalid A Alamry; Seik Weng Ng

doi:10.1107/S1600536811034453

. 2011 Aug 27;67(Pt 9):o2474. doi: 10.1107/S1600536811034453

4-(5,3′-Dimethyl-5′-oxo-2-phenyl-2′,5′-dihydro-2H-[3,4′]bipyrazol-1′-yl)benzenesulfonamide monohydrate

Abdullah M Asiri ^a,^b, Abdulrahman O Al-Youbi ^a, Hassan M Faidallah ^a, Khalid A Alamry ^a, Seik Weng Ng ^c,^a,^*

PMCID: PMC3200878 PMID: 22059030

Abstract

In the title compound, C₂₀H₁₉N₅O₃S·H₂O, the pyrazole ring is connected to a pyrazolone ring, and the two five-membered rings are aligned at 45.0 (1)°. The pyrazole ring is connected to a phenyl ring and the two are twisted by 42.7 (1)°. Finally, the pyrazolone ring is connected to a benzene ring and the two are twisted by 19.5 (1)°. The N—H and –NH₂ portions and the solvent water molecules are engaged in N—H⋯N, N—H⋯O and O—H⋯O hydrogen-bonding interactions to generate a three-dimensional network.

Related literature

For related pyrazole–benzenesulfonamides, see: Al-Youbi et al. (2011 ▶); Asiri et al. (2011 ▶).

Experimental

Crystal data

C₂₀H₁₉N₅O₃S·H₂O
M _r = 427.48
Monoclinic,
a = 11.1570 (5) Å
b = 12.3305 (5) Å
c = 14.9228 (5) Å
β = 107.142 (4)°
V = 1961.75 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.941, T _max = 0.960
9403 measured reflections
4382 independent reflections
3259 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.130
S = 1.01
4382 reflections
288 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536811034453/xu5305sup1.cif

e-67-o2474-sup1.cif^{(21.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034453/xu5305Isup2.hkl

e-67-o2474-Isup2.hkl^{(214.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811034453/xu5305Isup3.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
N3—H3⋯N2ⁱ	0.88 (1)	2.05 (1)	2.927 (3)	175 (2)
N5—H51⋯O1ⁱ	0.88 (1)	2.05 (1)	2.913 (3)	165 (2)
N5—H52⋯O1Wⁱⁱ	0.88 (1)	2.09 (1)	2.932 (3)	161 (2)
O1W—H11⋯O1	0.84 (1)	1.94 (1)	2.769 (2)	169 (3)
O1W—H12⋯O2ⁱⁱⁱ	0.84 (1)	2.38 (2)	3.158 (2)	154 (3)

Open in a new tab

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

Acknowledgments

The authors thank King Abdulaziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

This study extends on structural studies (Asiri et al., 2011; Al-Youbi et al., 2011) of compounds having a pyrrole ring as well as a benzesulfonamide unit, the combination of which is expected to lead to enhanced medicinal activity. The present compound is a pyrazole that is connected to a pyrazorolone (Scheme I, Fig. 1). The two five-membered ring-systems are aligned at 45.0 (1)°. The pyrazole ring-system is connected to a phenyl ring and the two are twisted by 42.7 (1)°; the pyrazolone ring-system is connected to a benzene ring and the two are twisted by 19.5 (1)°. The ═N—H and –NH₂ portions and the lattice water molecule are engagd in N—H···N, N—H···O and O—H···O hydrogen bonding interactions to generate a three-dimensional network (Table 1). The amino N atom shows pyramidal coordination.

Experimental

4-Acetoacetyl-3-methyl-1-(p-sulpfamylphenyl)-2-pyrazolin-5-one (0.05 mol) and phenylhydrazine (0.05 mol) were heated in a mixture of ethanol (50 ml) and acetic acid (50 ml) for 2 h. The mixture was allowed and the solid was collected and recrystallized from ethanol to give colorless prisms; m.p. 578–579 K.