4-(3-Phenyl-3,3a,4,5-tetra­hydro-2H-benzo[g]indazol-2-yl)benzene­sulfonamide ethanol monosolvate

Abdullah M Asiri; Hassan M Faidallah; Khalid A Alamry; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536812028474

. 2012 Jun 30;68(Pt 7):o2258–o2259. doi: 10.1107/S1600536812028474

4-(3-Phenyl-3,3a,4,5-tetrahydro-2H-benzo[g]indazol-2-yl)benzenesulfonamide ethanol monosolvate

Abdullah M Asiri ^a,^b,^‡, Hassan M Faidallah ^b, Khalid A Alamry ^a,^b, Seik Weng Ng ^c, Edward R T Tiekink ^c,^*

PMCID: PMC3394043 PMID: 22798908

Abstract

In the title compound ethanol monosolvate, C₂₃H₂₁N₃O₂S·C₂H₅OH, the dihydropyrazole ring is twisted about the Csp ³—Csp ³ bond. Nevertheless, the ring approximates a plane (r.m.s. deviation for the fitted atoms = 0.132 Å) and forms dihedral angles of 5.80 (13) and 12.29 (12)°, respectively, with the fused- and sulfonamide-benzene rings. As the dihydropyrazole C-bound phenyl group is roughly perpendicular to the dihydropyrazole ring [dihedral angle = 74.04 (15)°; the amino group is orientated to the same side of the molecule], to a first approximation, the molecule has a stunted T-shape. The cyclohexene ring adopts a half-chair conformation with the methylene C atom connected to the dihydropyrazole ring lying 0.665 (4) Å out of the plane of the five remaining atoms (r.m.s. deviation = 0.050 Å). The components of the asymmetric unit are connected by an O—H⋯O hydrogen bond. Further links between molecules leading to a three-dimensional architecture are of the type N—H⋯O.

Related literature

For a previous synthesis, see: Faidallah & Makki (1994 ▶). For the biological activity of related compounds, see: Faidallah et al. (2011 ▶). For the structure of the methyl analogue, see: Asiri et al. (2011 ▶).

Experimental

Crystal data

C₂₃H₂₁N₃O₂S·C₂H₆O
M _r = 449.56
Monoclinic,
a = 15.7556 (9) Å
b = 9.1789 (4) Å
c = 16.7515 (10) Å
β = 111.718 (7)°
V = 2250.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.761, T _max = 1.000
15054 measured reflections
5196 independent reflections
3971 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.156
S = 1.04
5196 reflections
301 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028474/xu5573sup1.cif

e-68-o2258-sup1.cif^{(24.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028474/xu5573Isup2.hkl

e-68-o2258-Isup2.hkl^{(254.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812028474/xu5573Isup3.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
O3—H3o⋯O1	0.84 (1)	2.04 (1)	2.875 (2)	175 (3)
N3—H1n⋯O3ⁱ	0.87 (1)	2.02 (1)	2.894 (3)	176 (3)
N3—H2n⋯O2ⁱⁱ	0.88 (1)	2.16 (1)	3.007 (3)	163 (2)

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

Acknowledgments

The authors are grateful to King Abdulaziz University for providing research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

The title compound, (I), reported previously in the literature (Faidallah & Makki, 1994), comprises a benzenesulfonamide unit which is grafted to a chemotherapeutic heterocycle pyrazole derivative, and therefore is a compound which is anticipated to exhibit enhanced activities (Faidallah et al., 2011).

In (I), Fig. 1, pyrazole ring is twisted about the C10—C11 bond (r.m.s. deviation for the fitted atoms = 0.132 Å). The cyclohexene ring adopts a half-chair conformation with the C9 atom lying 0.665 (4) Å out of the plane of the five remaining atoms (r.m.s. deviation = 0.050 Å). The fused-ring- and sulfonamide-benzene rings form dihedral angles of 5.80 (13) and 12.29 (12)°, respectively, with the least-squares plane through the pyrazole ring. By contrast, the pyrazole-C-bound phenyl group is almost perpendicular to the pyrazole ring, forming a dihedral angle of 74.04 (15)°, so that to a first approximation, the molecule has a stunted T-shape. The sulfonamide-amino group is orientated to the same side of the molecule as the pyrazole-C-bound benzene ring. While the sulfonamide-O1 atom is almost co-planar with the benzene ring, the O1—S1—C21—C20 torsion angle is -168.51 (17)°, the O2 atom is somewhat splayed [O2—S1—C21—C20 = -38.9 (2)°]. In the structure of the compound where the pyrazole-C-bound substituent is methyl rather than phenyl, the molecule has a shallow bowl-shaped conformation (Asiri et al., 2011).

The asymmetric unit comprises the organic molecule and a ethanol molecule of solvation with the primary connection between them being a O—H···O hydrogen bond, Table 1. Each amino-H forms a hydrogen bond to an oxygen atom so that each oxygen atom in the structure functions as an acceptor, Table 1, and that a three-dimensional architecture results, Fig. 2.

Experimental

A solution of 2-benzylidene-3,4-dihydro-2H-naphthalen-1-one (2.3 g, 0.01 M) in ethanol (50 ml) was refluxed with 4-hydrazinobenzenesulfonamide hydrochloride (2.2 g, 0.01 M) for 4 h. The reaction mixture was allowed to cool. The formed precipitate was filtered, washed with water, dried and recrystallized from ethanol. M.pt: 508–510 K cf. Lit. M.pt: 508 K (Faidallah & Makki, 1994). Yield: 70%.