Butyl 4-(4-methyl­benzene­sulfonamido)­benzoate

Ghulam Mustafa; Mehmet Akkurt; Yılmaz Dağdemir; Islam Ullah Khan

doi:10.1107/S1600536812015413

. 2012 Apr 28;68(Pt 5):o1541. doi: 10.1107/S1600536812015413

Butyl 4-(4-methylbenzenesulfonamido)benzoate

Ghulam Mustafa ^a,^*, Mehmet Akkurt ^b,^*, Yılmaz Dağdemir ^b, Islam Ullah Khan ^a

PMCID: PMC3344642 PMID: 22590404

Abstract

In the title compound, C₁₈H₂₁NO₄S, the aromatic rings are almost normal to each other, with a dihedral angle of 89.27 (18)°. The molecular conformation is stabilized by an intramolecular C—H⋯O interaction, which generates an S(6) motif. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds lead to the formation of chains propagating along [010]. Neighbouring chains are linked via a C—H⋯π interaction. The –CH₂CH₂CH₃ atoms of the butyl group are disordered over two sets of sites, with a refined site-occupancy ratio of 0.536 (16):0.464 (16).

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 ▶). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₈H₂₁NO₄S
M _r = 347.43
Monoclinic,
a = 17.8216 (13) Å
b = 8.2702 (6) Å
c = 11.9282 (8) Å
β = 91.001 (3)°
V = 1757.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.33 × 0.25 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
13164 measured reflections
3557 independent reflections
2287 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.072
wR(F ²) = 0.218
S = 1.05
3557 reflections
224 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 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/S1600536812015413/su2404sup1.cif

e-68-o1541-sup1.cif^{(30.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015413/su2404Isup2.hkl

e-68-o1541-Isup2.hkl^{(178KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812015413/su2404Isup3.cml

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

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

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.86	2.11	2.868 (4)	146
C9—H9⋯O2	0.93	2.36	3.015 (4)	127
C10—H10⋯O1ⁱⁱ	0.93	2.53	3.453 (4)	173
C1—H1C⋯Cg1ⁱⁱⁱ	0.96	2.76	3.639 (6)	153

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

Acknowledgments

The authors are grateful to Mr Muhammad Nadeem Arshad for his assistance and 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 describe herein the synthesis and crystal structure of the title compound.

As seen in Fig. 1, the two aromatic rings (C2—C7) and (C8—C13) are almost normal to each other, with a dihedral angle of 89.27 (18)°. The S atom has a distorted tetrahedral coordination geometry [S1—O1 = 1.411 (3), S1—O2 = 1.419 (3), S1— N1 = 1.626 (3), S1—C5 = 1.760 (4) Å, O1—S1—O2 = 120.43 (15), O1—S1—N1 = 105.23 (17), O1—S1 —C5 = 106.92 (16), O2—S1—N1 = 109.21 (16), O2—S1—C5 = 108.23 (17) and N1— S1—C5 = 105.94 (15)°]. 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 the title compound is stabilized by an intramolecular C—H···O interaction, generating an S(6) motif (Table 1; Bernstein et al., 1995). In the crystal, N—H···O and C—H···O hydrogen bonds lead to the formation of chains propagating along [010] - see Fig. 2 and Table 1. Neighbouring chains are linked via a C—H···π interaction (Table 1).

Experimental

To an aquious solution of p-amino benzoic acid (1.0 g, 7.3 mmol), sodium carbonate (1 N) was added to adjust the pH to 8. p-toluenesulfonyl chloride (1.80 g, 9.48 mmol) was then added and the mixture was stirred at room temperature keeping the pH of the mixture up to 8 with occasional addition of sodium carbonate solution. The progress and completion of the reaction was confirmed by TLC and conversion of the suspension into a clear solution. After 2 h, the mixture was poured into a beaker and the pH was adjusted to 2.0 by addition of 1 N HCl. Precipitates were produced which were filtered and washed with distilled water. The prepared sulfonamide (4-(toluene-4-sulfonylamino)-benzoic acid) (1.0 g, 3.43 mmol), DMF (10 ml) and n-hexane washed with sodium hydride (0.25 g, 10.31 mmol) were stirred at room temperature for 40 min, followed by the addition of butyl iodide (0.94 g, 5.15 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 and washed twice with distilled water. Crystallization in chloroform gave long block-like pale-yellow X-ray quality crystals of the title compound.