Propyl 2-(4-methyl­benzene­sulfonamido)­benzoate

Ghulam Mustafa; Tahir Muhmood; Islam Ullah Khan; Mehmet Akkurt

doi:10.1107/S1600536812015528

. 2012 Apr 13;68(Pt 5):o1388. doi: 10.1107/S1600536812015528

Propyl 2-(4-methylbenzenesulfonamido)benzoate

Ghulam Mustafa ^a, Tahir Muhmood ^a, Islam Ullah Khan ^a, Mehmet Akkurt ^b,^*

PMCID: PMC3344515 PMID: 22590277

Abstract

In the title compound, C₁₇H₁₉NO₄S, the terminal ethyl group is disordered over two sets of sites, with refined site occupancies of 0.536 (7) and 0.464 (7). The dihedral angle between the two aromatic rings is 81.92 (12)°. The molecular conformation is stabilized by intramolecular N—H⋯O and C—H⋯O hydrogen bonds, which generate S(6) motifs. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For related structures, see: Mustafa et al. (2010 ▶, 2011 ▶, 2012 ▶); Khan et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₉NO₄S
M _r = 333.40
Monoclinic,
a = 16.206 (5) Å
b = 8.513 (2) Å
c = 12.021 (3) Å
β = 92.352 (2)°
V = 1657.0 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.34 × 0.22 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
15110 measured reflections
4039 independent reflections
2343 reflections with I > 2σ(I)
R _int = 0.071

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.178
S = 0.95
4039 reflections
209 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015528/hg5208sup1.cif

e-68-o1388-sup1.cif^{(27.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015528/hg5208Isup2.hkl

e-68-o1388-Isup2.hkl^{(198KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812015528/hg5208Isup3.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
N1—H1⋯O3	0.86	2.11	2.643 (3)	119
C10—H10⋯O1ⁱ	0.93	2.49	3.391 (3)	163
C9—H12⋯O2	0.93	2.36	3.027 (3)	128

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the Higher Education Commission (HEC), Pakistan, for financial support.

supplementary crystallographic information

Comment

As part of our ongoing studies of sulfonamides with potential biological properties (Mustafa et al., 2010, 2011, 2012; Khan et al., 2011), we now describe the title compound, propyl 2-{[(4-methylphenyl)sulfonyl]amino}benzoate, (I).

In the title molecule (I), (Fig. 1), the dihedral angle between the two benzene rings (C2—C7) and (C8—C13) is 81.92 (12)°. The C—S—N—C torsion angle is 61.6 (2)°. All the bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those found for similar structures (Mustafa et al., 2010; 2011, 2012; Khan et al., 2011).

The molecular conformation of (I) is stabilized by intramolecular N—H···O and C—H···O hydrogen-bond interactions, generating S(6) motifs (Table 1). The crystal structure is stabilized by C—H···O hydrogen bonds, forming chains along the b axis (Table 1, Fig. 2).

Experimental

To an aqueous solution of o-amino benzoic acid (1.0 g, 7.3 mmol), sodium carbonate (1 N) was added to adjust the pH 8. Then p-toluenesulfonyl chloride (1.80 g, 9.48 mmol) was added and the mixture stirred at room temperature keeping the pH of the mixture up to 8.0 with occasional addition of sodium carbonate solution. Progress and completion of the reaction was confirmed by TLC and conversion of suspension into clear solution. After 2 h, whole mixture was poured into a beaker and the pH was adjusted to 2.0 by 1 N HCl. Precipitates were produced which were filtered and washed with distilled water.

The prepared sulfonamide (2-(Toluene-4-sulfonylamino)-benzoic acid) (1.0 g, 3.43 mmol), DMF (10 ml) and n-hexane washed sodium hydride (0.25 g, 10.31 mmol) were stirred at room temperature for 40 min followed by the addition of propyl iodide (0.76 g, 4.56 mmol). The whole reaction mixture was stirred till the completion of the reaction and poured into crushed ice in a beaker. The pH of the mixture was adjusted to 4.0 with 1 N HCl. Precipitates were produced, filtered, washed twice with distilled water and crystallized in chloroform.