Cyano­methyl 4-(4-methyl­benzene­sulfonamido)­benzoate

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

doi:10.1107/S1600536812017126

. 2012 Apr 21;68(Pt 5):o1488. doi: 10.1107/S1600536812017126

Cyanomethyl 4-(4-methylbenzenesulfonamido)benzoate

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

PMCID: PMC3344598 PMID: 22590360

Abstract

The title molecule, C₁₆H₁₄N₂O₄S, adopts an L-shaped conformation, with the central C—S—N—C torsion angle being −69.1 (3)°. The two benzene rings form a dihedral angle of 89.94 (15)°. The molecular conformation may be influenced by a weak intramolecular C—H⋯O hydrogen bond which generates an S(6) ring motif. In the crystal, molecules are linked by N—H⋯O and weak C—H⋯O hydrogen bonds, forming chains propagating along the b axis. Weak C—H⋯N hydrogen bonds connect the chains into a two-dimensional network parallel to (011). The crystal studied was an inversion twin, the ratio of components being 0.7 (1):0.3 (1).

Related literature

For related structures, see: Mustafa et al. (2010 ▶, 2011 ▶, 2012a ▶,b ▶); Khan et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₆H₁₄N₂O₄S
M _r = 330.36
Monoclinic,
a = 5.9360 (3) Å
b = 8.1992 (4) Å
c = 15.9068 (8) Å
β = 91.222 (3)°
V = 774.02 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.28 × 0.23 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer
6266 measured reflections
3077 independent reflections
2306 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.106
S = 1.01
3077 reflections
210 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ▶), 1248 Freidel pairs
Flack parameter: 0.30 (10)

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/S1600536812017126/lh5455sup1.cif

e-68-o1488-sup1.cif^{(23.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017126/lh5455Isup2.hkl

e-68-o1488-Isup2.hkl^{(151KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812017126/lh5455Isup3.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⋯O3ⁱ	0.86	2.21	2.904 (3)	138
C1—H1A⋯O2ⁱⁱ	0.96	2.58	3.446 (5)	150
C9—H9⋯O2	0.93	2.38	3.025 (4)	126
C10—H10⋯O1ⁱⁱⁱ	0.93	2.51	3.431 (4)	172
C12—H12⋯N2^iv	0.93	2.62	3.426 (6)	146

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

Acknowledgments

The authors are grateful to Mr Muhammad Shafiq 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, 2012a,b; Khan et al., 2011), the crystal structure of the title compound (I) has been determined.

The molecular structure of (I) (Fig. 1), has a L-shaped conformation, with the central C5—S1—N1—C8 torsion angle being -69.1 (3)°. The two benzene rings (C2—C7) and (C8—C13) are nearly perpendicular to each other, with a dihedral angle of 89.94 (15)°. All the bond lengths (Allen et al., 1987) and angles are normal (Mustafa et al., 2010; 2011, 2012a,b; Khan et al., 2011).

The title molecule exhibits an S(6) motif (Bernstein et al., 1995) formed by a weak intramolecular C—H···O hydrogen bond interaction (Table 1). In the crystal, molecules are linked by N—H···O and weak C—H···O hydrogen bonds forming chains propagating along the b axis. Weak intermolecular C—H···N hydrogen bonds connect the chains into a two dimensional netwok (Table 1, Fig. 2).

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. Then p-toluenesulfonyl chloride (1.80 g, 9.48 mmol) was added and the mixture was stirred at room temperature keeping the pH of the mixture at 8.0 with occasional addition of sodium carbonate solution. Progress and completion of the reaction was confirmed by TLC and conversion of the suspension into a clear solution. After 2 h, whole mixture was poured into a beaker and the pH was adjusted to 2.0 by 1 N HCl. Pprecipitates 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 sodium hydride (0.25 g, 10.31 mmol) were stirred at room temperature for 40 min followed by the addition of chloroacetonitrile (0.34 g, 4.46 mmol). The whole reaction mixture was stirred at 353 K 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. Crystals suitable for X-ray diffraction were grown from a chloroform solution of the title compound.