4-Methyl-N-{2-[(E)-3-oxo-3-phenyl­prop-1-en-1-yl]phen­yl}benzene­sulfonamide

Sung-Gon Kim

doi:10.1107/S1600536814015311

. 2014 Jul 5;70(Pt 8):o851. doi: 10.1107/S1600536814015311

4-Methyl-N-{2-[(E)-3-oxo-3-phenylprop-1-en-1-yl]phenyl}benzenesulfonamide

Sung-Gon Kim ^a,^*

PMCID: PMC4158538 PMID: 25249902

Abstract

In the title compound, C₂₂H₁₉NO₃S, the terminal phenyl and methylphenyl rings are twisted by 37.35 (12) and 49.08 (13)°, respectively, to the central benzene ring. In the crystal, molecules are linked by classical N—H⋯O hydrogen bonds and weak C—H⋯O hydrogen bonds into a three-dimensional supramolecular network.

Keywords: crystal structure

Related literature

For applications of sulfonamides in the fields of chemistry, biology and pharmacology, see: Chohan et al. (2010 ▶); El-Sayed et al. (2011 ▶); Seri et al. (2000 ▶); Suparan et al. (2000 ▶). For related structures, see: Murugavel et al. (2012 ▶); Zhang et al. (2010 ▶); Mughal et al. (2012 ▶).

Experimental

Crystal data

C₂₂H₁₉NO₃S
M _r = 377.44
Monoclinic,
a = 8.9356 (7) Å
b = 10.8873 (8) Å
c = 19.3122 (14) Å
β = 99.472 (2)°
V = 1853.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 200 K
0.19 × 0.12 × 0.06 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.964, T _max = 0.988
13392 measured reflections
4589 independent reflections
2366 reflections with I > 2σ(I)
R _int = 0.066

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.154
S = 1.01
4589 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814015311/xu5798sup1.cif

e-70-0o851-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015311/xu5798Isup2.hkl

e-70-0o851-Isup2.hkl^{(224.8KB, hkl)}

Click here for additional data file.^{(7KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814015311/xu5798Isup3.cml

CCDC reference: 1010977

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	2.24	2.839 (3)	125
C4—H4⋯O2ⁱ	0.95	2.51	3.272 (4)	137
C18—H18⋯O3ⁱⁱ	0.95	2.44	3.373 (3)	167
C22—H22B⋯O1ⁱⁱⁱ	0.98	2.58	3.466 (4)	150

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

Acknowledgments

This work was supported by Kyonggi University Research Grant 2014.

supplementary crystallographic information

S1. Chemical context

S2. Structural commentary

For related structures, see: Murugavel et al. (2012); Zhang et al. (2010). Sulfonamides, which are already known as sulfa drugs, are an important class of compounds in the field of chemistry, biology and pharmacology. Several sulfonamide derivatives are used as chemotherapeutic agents for their antibacterial, antifungal, antitumor and hypoglycemic (Chohan et al., 2010; El-Sayed et al., 2011; Seri et al., 2000). In addition, some sulfonamide derivatives have been shown to inhibit on carbonic anhydrases (Suparan et al., 2000). In view of these potential applications and in continuation of our work, the structure of the title compound has been carried out and the results are presented here.

X-ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The geometry around atoms S and N are distorted tetrahedral and planar trigonal, respectively. The average S—O bond length is 1.427 (2) Å, while the S—N and S—C bond lengths are 1.638 (3) and 1.757 (3), respectively. The dihedral angle between the vinylphenyl ring (C1—C6) and the methylphenyl ring (C16—C21) is 49.08 (13)^o, and the dihedral angle between the vinylphenyl ring (C1—C6) and ketophenyl (C10—C15) ring is 37.35 (12)^o. The sulfonamide torsion angle 1s 64.0 (2)^o for C2—N1—S1—C16. The C==C double bond is in an E conformation and the vinylcarbonyl groups adopt extended conformations.

S3. Supramolecular features

S4. Database survey

S5. Synthesis and crystallization

A solution of 4 M Na₂CO₃ in water (10 mL) was added to a solution of 2-aminobenzyl alcohol (5.0 mmol) and p-toluenesulfonyl chloride (5.5 mmol) in THF (10 mL). After stirring at room temperature for 24 h, the reaction mixture was poured into cold water and extracted with EtOAc. The resultant organic layer was washed with brine and dried over MgSO₄. The resulting residue was purified by silica gel chromatography to afford 2-(toluensulfonylamino)benzyl alcohol. Next, to solutionof 2-(toluensulfonylamino)benzyl alcohol (3.0 mmol) in CH₂Cl₂ (10 mL) was added excess MnO₂ (15 mmol). After stirring for at room temperature for 36 h, the reaction mixture was filtered under celite pad and purified by silica gel chromatography to afford 2-(toluensulfonylamino)benzaldehyde. To a solution of phenacyltriphenylphosphonium bromide (1.1 mmol) in toluene (5 mL) was added NaH (1.2 mmol) at 273 K. After stirring at 273 K for 1 h, to the reactin mixture, 2-(toluensulfonylamino)benzaldehyde (1.0 mmol) was added. After stirring at room temperature for 24 h, the reaction mixture was poured into water and extracted with EtOAc. The resultant organic layer was washed with brine and dried over MgSO₄. Theresulting residue was purified by silica gel chromatography to afford the title compound. Crystals suitable for X-ray analysis were obtained by recryatallization from an n-hexane/CH₂Cl₂ solution.

S6. Refinement

All H atoms were positioned geometrically, (C—H = 0.95–0.96 Å) and constrained to ride on their parent atoms, with U_iso(H) = xUeq(C), where x = 1.2 for all other H atoms.