2-(4-Chloro­phen­yl)-5-(cyclo­hex-1-en-1-yl)-3-(4-methyl­phenyl­sulfon­yl)-1-phenyl­imidazolidin-4-one

S Ranjith; K SakthiMurugesan; A SubbiahPandi; K Namitharan; K Pitchumani

doi:10.1107/S1600536811028133

. 2011 Jul 23;67(Pt 8):o2071. doi: 10.1107/S1600536811028133

2-(4-Chlorophenyl)-5-(cyclohex-1-en-1-yl)-3-(4-methylphenylsulfonyl)-1-phenylimidazolidin-4-one

S Ranjith ^a, K SakthiMurugesan ^a, A SubbiahPandi ^a,^*, K Namitharan ^b, K Pitchumani ^b

PMCID: PMC3213516 PMID: 22091095

Abstract

In the title compound, C₂₈H₂₇ClN₂O₃S, the central imidazolidine ring adopts an envelope conformation with the C atom bearing the chlorophenyl ring at the flap. The geometry around the S atom is distorted tetrahedral. Three methylene groups of the cyclohexene ring are disordered over two sets of sites [site occupancies = 0.562 (10) and 0.438 (10)]. The crystal packing is stabilized by C—H⋯π interactions.

Related literature

For the biological activity of sulfonamides, see: Zareef et al. (2007 ▶); Chohan & Shad (2008 ▶); Pomarnacka & Kozlarska-Kedra (2003 ▶); Nieto et al. (2005 ▶); Wang et al. (1995 ▶). For a related structure, see: Ranjith et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For ring asymmetry parameters, see: Nardelli et al. (1983 ▶).

Experimental

Crystal data

C₂₈H₂₇ClN₂O₃S
M _r = 507.03
Monoclinic,
a = 10.9974 (3) Å
b = 13.4095 (4) Å
c = 17.4434 (5) Å
β = 105.103 (2)°
V = 2483.52 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.934, T _max = 0.950
32488 measured reflections
7366 independent reflections
4844 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.139
S = 1.01
7366 reflections
346 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028133/bt5573sup1.cif

e-67-o2071-sup1.cif^{(27.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028133/bt5573Isup2.hkl

e-67-o2071-Isup2.hkl^{(353.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811028133/bt5573Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg2 and Cg4 are the centroids of the C2–C7 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cg4ⁱ	0.96	2.91	3.490 (3)	120
C11—H11⋯Cg2ⁱ	0.93	2.86	3.612 (2)	139

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Symmetry code: (i) Inline graphic .

Acknowledgments

SR and ASP thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

Sulfonamides have widely been recognized for their wide variety of pharmacological activities such as antibacterial, antitumor, anti-carbonic anhydrase, diuretic, hypoglycaemic, antithyroid and protease inhibitory activity. Sulfonamides have also been used clinically as antimalarial agents (Zareef et al., 2007), particularly sulfadiazine and sulfadoxine. Due to their significant pharmacology applications and widespread use in medicine, these compounds have also gained attention in bioinorganic and metal-based (Chohan et al., 2008) drug chemistry. Sulfonamide derivatives are well known drugs and are used to control diseases caused by bacterial infections. Benzene sulfonamide derivatives are known to exhibit anticancer and HIV activities (Pomarnacka & Kozlarska-Kedra, 2003) and antibacterial activities (Nieto et al., 2005). Imidazolidine compounds are important intermediates and building blocks in the construction of various biologically active compounds (Wang et al., 1995). Against this background, and in order to obtain detailed information on molecular conformations in the solid state, an X-ray study of the title compound was carried out.

X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The geometry around the S atom is distorted tetrahedral, comprising two O atoms of the sulfonyl group, a C atom of a phenyl ring and the imidazolidine N atom. The S–O, S–C, and S–N distances are 1.416 (2), 1.747 (2) and 1.677 (2) Å, respectively, these are comparable as observed in similar structures (Ranjith et al., 2011). The atom Cl1 is deviated by 0.136 (1)Å from the leastsquares plane of the rings C9–C14. The S atom exhibits significant deviation from that of a regular tetrahedron, with the largest deviations for the O–S–O [O1–S1–O2 121.2 (9)°] and O–S–N angles [O1–S1–N1 106.4 (7)°]. The widening of the angles may be due to repulsive interactions between the two short S=O bonds, similar to what is observed in related structures (Ranjith et al., 2011).

The imidazolidine ring adopts envelope conformation, with the puckering parameters q₂ and φ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters,Δ, (Nardelli et al., 1983) as follows: q₂=0.1230 (17) Å, φ=211.7 (8)°, Δ_s(C8)=1.50 (17) and the cyclohexane ring adopts half-chair conformation, in addition to with the puckering parameters q₂ and φ (Cremer & Pople, 1975) and the smallest displacement asymmetric parameters,Δ, (Nardelli et al., 1983) as follows: q₂=0.399 (7) Å, φ=127.2 (8)°, Δ_s(C24)= 18.4 (7). In the crystal, the molecules form layers that are linked by π···π stacking interactions between the imidazolidine and benzene [C9—C14] rings [centroid–centroid distances = 3.7406 (9) Å].

Experimental

4-Toluenesulfonyl azide (1.3 mmol), 1-ethynyl cyclohexene (1.2 mmol), 4-chlorophenyl N-phenylnitrone (1.0 mmol) and triethylamine (2 mmol) were successively added to Cu¹—Y zeolite (30 mg) in dichloromethane under N₂ atmosphere. After stirring at room temperature for the 6 h, the mixture was diluted with dichloromethane. After removing the catalyst by filtration, followed by solvent evaporation, the resulting crude product was finally purified by column chromatography (silica gel). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in acetone at room temperature.