N-{4-[(3-Methyl­phen­yl)sulfamo­yl]phen­yl}benzamide

Manu Lahtinen; Jyothi Damodara; Poornima Upadhyaya; Nonappa; Erkki Kolehmainen

doi:10.1107/S1600536811040384

. 2011 Oct 8;67(Pt 11):o2866. doi: 10.1107/S1600536811040384

N-{4-[(3-Methylphenyl)sulfamoyl]phenyl}benzamide

Manu Lahtinen ^a, Jyothi Damodara ^b,^*, Poornima Upadhyaya ^b, Nonappa ^a, Erkki Kolehmainen ^a

PMCID: PMC3247601 PMID: 22219906

Abstract

In the title compound, C₂₀H₁₈N₂O₃S, the dihedral angle between the central benzene ring and the amide group is 24.1 (3)° and that between this ring and the aromatic ring of the tolyl group is 68.2 (16)°. In the crystal, adjacent molecules are linked by N—H⋯O hydrogen bonds into a linear chain running along [100]. Weak C—H⋯O contacts also occur. Extensive weak π–π interactions exist from both face-to-face and face-to-edge interactions occur between the aromatic rings [centroid–centroid distances = 3.612 (2) and 4.843 (2) Å].

Related literature

For related structures, see: Aziz-ur-Rehman et al. (2010a ▶,b ▶,c ▶); Khan et al. (2010 ▶); Shad et al. (2008 ▶, 2009 ▶); Yasmeen et al. (2010 ▶); Gowda et al. (2007 ▶).

Experimental

Crystal data

C₂₀H₁₈N₂O₃S
M _r = 366.42
Triclinic,
a = 8.5344 (2) Å
b = 8.8477 (3) Å
c = 12.4383 (4) Å
α = 77.924 (2)°
β = 75.382 (2)°
γ = 86.537 (2)°
V = 888.67 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 123 K
0.32 × 0.20 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer with Bruker APEXII detector
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.675, T _max = 0.746
11971 measured reflections
3122 independent reflections
2591 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.088
S = 1.04
3122 reflections
242 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶; Otwinowski et al. 2003 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006) ▶; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040384/ng5238sup1.cif

e-67-o2866-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040384/ng5238Isup4.hkl

e-67-o2866-Isup4.hkl^{(150KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811040384/ng5238Isup3.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
N7—H7⋯O27ⁱ	0.86 (2)	1.99 (2)	2.813 (2)	160 (2)
N25—H25⋯O17ⁱⁱ	0.84 (2)	2.38 (2)	3.062 (2)	140 (2)
C4—H4⋯O18	0.95	2.40	3.047 (3)	125

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

supplementary crystallographic information

Comment

Sulfonamides are very important class of compounds because of their antibacterial and enzyme inhibitor properties as well as their extensive use in medicine. As a contribution to a structural study of sulfonamide derivatives (Khan et al., 2010; Aziz-ur-Rehman et al., 2010a,b,c; Yasmeen et al., 2010; Gowda et al. 2007), we report here the title compound, N-{4-[(3-methylphenyl)sulfamoyl]phenyl}benzamide (I).

Compound (I) crystallizes in triclinic space group P-1 (No. 2) without any solvent molecules and having a single molecule in an asymmetric unit (Fig. 1). The sulfonyl and amide groups show characteristic geometries (tetrahedral and planar conformation, respectively) having typical bond distances and angles for these groups (see Tables). The dihedral angles between the central phenyl group [C(19)>C(24)] and amide group N(25)—C(26)—O(27) is about 24° and the tilting of terminal groups bonded to the sulfonamide is about 111°. The molecules are packed in infinite chains along tne a-axis enabling the hydrogen bond network to occur via a axis, whereas along c axis the packing is more columnar forming "box"-like shapes cornered by the sulfonyl groups (Fig. 2). The infinite hydrogen bond networks, along a axis, occur via N(7)—H(7)···O(27) and N(25)—H(25)···O(17) donor-acceptors with d(D···A) bond distances of 2.813 (2) and 3.062 (2) Å in angles of about 160° and 140°, respectively. Three weaker intramolecular hydrogen bonds exist between aromatic ring H atoms (H4, H20 H23) and O atoms O(27) and O(18) having d(D···A) distances of about 2.9–3.0 Å and having fairly unfavorable contact angles varying 105–125°. In addition extensive weak π-π interactions exist in the structure as both face-to-face and face-to-edge interactions occurs between the phenyl rings (Fig. 3).

Experimental

4-Amino-N-(3-methylphenyl)benzenesulfonamide (0.5 g, 1.91 mmol) was taken in 20 ml dry EtOH and then benzoyl chloride (0.22 ml, 1.91 mmol) was added dropwise. The reaction medium was maintained at basic condition by adding pyridine to neutralize the produced HCl. The mixture was refluxed at 343 K for 2 h to complete the reaction. The progress of the reaction was monitored by TLC. A white precipitate obtained was filtered and purified in acetone to constant melting point. Few crystals suitable for a single-crystal structure determination were recrystallized from ethanol-acetone solution.