N-(2-Formyl­phen­yl)benzene­sulfonamide

S Thenmozhi; S Ranjith; A SubbiahPandi; V Dhayalan; A K MohanaKrishnan

doi:10.1107/S1600536809032681

. 2009 Aug 22;65(Pt 9):o2210. doi: 10.1107/S1600536809032681

N-(2-Formylphenyl)benzenesulfonamide

S Thenmozhi ^a, S Ranjith ^a, A SubbiahPandi ^a,^*, V Dhayalan ^b, A K MohanaKrishnan ^b

PMCID: PMC2969910 PMID: 21577611

Abstract

In the title compound, C₁₃H₁₁NO₃S, the two aromatic rings are oriented at an angle of 88.18 (8)°. Intramolecular N—H⋯O and C—H⋯O hydrogen bonds are observed, each of which generates an S(6) ring motif. In the crystal, molecules are linked into C(7) chains along [010] by intermolecular C—H⋯O hydrogen bonds. The structure is further stabilized by intermolecular C—H⋯π interactions involving the sulfonyl-bound phenyl ring.

Related literature

For the biological activity of sulfonamides, see: Zareef et al. (2007 ▶); Chohan et al. (2007 ▶); Brown (1971 ▶); Pomarnacka & Kozlarska-Kedra (2003 ▶); Sethu Sankar et al. (2002 ▶). For related structures, see: Bassindale (1984 ▶); Cotton & Stokley (1970 ▶); Usha et al. (2005 ▶); Zhu et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₃H₁₁NO₃S
M _r = 261.29
Triclinic,
a = 7.7656 (2) Å
b = 9.0080 (2) Å
c = 9.5855 (2) Å
α = 86.293 (1)°
β = 77.912 (1)°
γ = 68.826 (1)°
V = 611.35 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 K
0.21 × 0.19 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.768, T _max = 0.956
15490 measured reflections
3960 independent reflections
3228 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.119
S = 1.02
3960 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 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 datablocks global, I. DOI: 10.1107/S1600536809032681/ci2869sup1.cif

e-65-o2210-sup1.cif^{(17KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032681/ci2869Isup2.hkl

e-65-o2210-Isup2.hkl^{(190.1KB, hkl)}

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
N1—H1⋯O3	0.80 (2)	1.99 (2)	2.6751 (19)	144 (2)
C2—H2⋯O1	0.93	2.46	3.0879 (18)	125
C3—H3⋯O2ⁱ	0.93	2.56	3.2691 (19)	133
C5—H5⋯Cg1ⁱⁱ	0.93	2.80	3.700 (2)	162

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 is the centroid of the C8–C13 ring.

Acknowledgments

ST and AS thank Dr Babu Varghese, SAIF, IIT-Madras, Chennai, India, for his help with the data collection.

supplementary crystallographic information

Comment

Sulfonamides have been recognized for their wide variety of pharmacological activities such as antibacterial, antitumor, anti-carbonic anhydrase, diuretic, hypoglycaemic, antithyroid and protease inhibitory activities. Sulfonamides particularly sulfadiazine and sulfadoxine have been used clinically as antimalarial agents (Zareef et al., 2007). Due to their significant pharmacological applications and widespread use in medicine, these compounds have also gained attention in bioinorganic and metal-based drug chemistry (Chohan et al., 2007). Sulfonamide derivates are well known drugs and are used to control diseases caused by bacterial infections. The antibacterial action of this group of drugs is exerted by the complete inhibition of dihydropteroate synthase enzyme towards the p-amino benzonate (Brown, 1971). Benzene sulfonamide derivatives are known to exhibit anticancer and HIV activities (Pomarnacka & Kozlarska-Kedra, 2003). The sulfonamides inhibit the growth of bacterial organism and are also useful for treating urinary and gastrointestinal infections (Sethu Sankar et al., 2002). In view of this medicinal importance, the crystal structure determination of the title compound (Fig.1) was carried out and the results are presented here.

Atom S1 has a distorted tetrahedral configuration. The widening of angle O1—S1—O2 [119.76 (7)°] and narrowing of angle C8—S1—N1 [106.08 (6)°] from the ideal tetrahedral value are attributed to the Thorpe-Ingold effect (Bassindale, 1984). The two aromatic rings are oriented at an angle of 88.18 (8)°. The angles around atom S1 deviate significantly from the regular tetrahedral value, with the largest deviation of 119.7 (7)° for O1—S1—O2 angle. This may be due to non-bonding interactions between S—O bonds (Cotton & Stokley, 1970). The aldyhyde group is coplanar with the benzene ring, as evidenced by the torsion angle C1—C6—C7—O3 of -2.2 (3)°. The geometrical parameters agree well with those reported for related sulfonamide structures (Usha et al., 2005; Zhu et al., 2008). Intramolecular N1—H1···O3 and C2—H2···O1 hydrogen bonds are observed, each of which generates an S(6) ring motif (Bernstein et al., 1995).

Intermolecular C—H···O hydrogen bonds involving atoms C3 and O2 link molecules into C(7) chains running along the [010] (Fig. 2). The crystal packing is further stabilized by C—H···π interactions involving the sulfonyl-bound phenyl ring.

Experimental

N-[2-(Hydroxymethyl)phenyl]benzenesulfonamide (2 g, 7.6 mmol) was added to a solution of pyridinium chlorochromate (3.25 g, 15.11 mmol) in dry dichloromethane (20 ml) at room temperature and the reaction mixture was stirred for 4 h. The solvent was removed to obtain a crude aldehyde as a white solid. Single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution.