N-(4-Methyl­phenyl­sulfon­yl)succinamic acid

H Purandara; Sabine Foro; B Thimme Gowda

doi:10.1107/S1600536812023276

. 2012 May 26;68(Pt 6):o1885. doi: 10.1107/S1600536812023276

N-(4-Methylphenylsulfonyl)succinamic acid

H Purandara ^a, Sabine Foro ^b, B Thimme Gowda ^a,^*

PMCID: PMC3379445 PMID: 22719643

Abstract

In the crystal structure of the title compound, C₁₁H₁₃NO₅S, the amide C=O and the carboxyl C=O groups of the acid segment orient themselves away from each other. The dihedral angle between the benzene ring and the amide group is 69.0 (2)°. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link the molecules into layers parallel to the bc plane.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Gowda et al. (2000 ▶); Saraswathi et al. (2011 ▶), of N-chloroarylamides, see: Gowda & Rao (1989 ▶); Jyothi & Gowda (2004 ▶) and of N-bromoarylsulfonamides, see: Gowda & Mahadevappa (1983 ▶); Usha & Gowda (2006 ▶).

Experimental

Crystal data

C₁₁H₁₃NO₅S
M _r = 271.28
Monoclinic,
a = 10.2496 (9) Å
b = 17.041 (2) Å
c = 7.4721 (6) Å
β = 101.909 (9)°
V = 1277.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.48 × 0.32 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.883, T _max = 0.959
4739 measured reflections
2597 independent reflections
2107 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.110
S = 1.12
2597 reflections
170 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812023276/rz2761sup1.cif

e-68-o1885-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023276/rz2761Isup2.hkl

e-68-o1885-Isup2.hkl^{(127.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812023276/rz2761Isup3.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—H1N⋯O1ⁱ	0.83 (2)	2.14 (2)	2.948 (2)	164 (2)
O5—H5O⋯O4ⁱⁱ	0.83 (2)	1.83 (2)	2.663 (3)	178 (3)

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

Acknowledgments

HP thanks the Department of Science and Technology, Government of India, New Delhi, for a research fellowship under its INSPIRE Program. BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to faculty.

supplementary crystallographic information

Comment

As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000; Saraswathi et al., 2011); N-chloroarylsulfonamides (Gowda & Rao, 1989; Jyothi & Gowda, 2004) and N-bromoaryl- sulfonamides (Gowda & Mahadevappa, 1983; Usha & Gowda, 2006), in the present work, the crystal structure of N-(4-methylphenylsulfonyl)succinamic acid has been determined (Fig. 1). The conformations of the N—H and C=O bonds in the amide segment are anti to each other. Further, the amide C═O and the carboxyl C═O of the acid segment orient themselves away from each other, in contrast to the anti conformation observed between the the amide oxygen and the carboxyl oxygen in N-(4-methylphenyl)-succinamic acid (I) (Saraswathi et al., 2011). But both the amide oxygen and the carboxyl oxygen are anti to the H atoms on the adjacent –CH₂ groups, in both the compounds.

In the title compound, the C═O and O—H bonds of the acid group are in syn position to each other, similar to that observed in (I). The molecule is bent at the S-atom with the C1–S1–N1–C7 torsion angle of 79.2 (1)°. Further, the dihedral angle between the phenyl ring and the amide group is 69.0 (2)°. In the crystal, the pairs of O—H···O and N—H···O intermolecular hydrogen bonds link the molecules into layers parallel to the bc plane (Table 1, Fig. 2).

Experimental

Succinic anhydride (0.015 mole) and 4-dimethylaminopyridine (0.01 mole) were added to a solution of p-toluenesulfonamide (0.01 mole) in dichloromethane. The reaction mixture was strirred for 18 h at room temperature and set aside for completion of the reaction. The reaction mixture was concentrated to dryness. The resultant title compound was washed with dilute HCl and then with water thoroughly, to remove the unreacted base and the succinic anhydride. It was recrystallized to constant melting point from ethyl acetate (173–175 °C). The purity of the compound was checked and characterized by its infrared spectrum. Prism-like colourless single crystals used in X-ray diffraction studies were grown by slow evaporation of an ethyl acetate solution at room temperature.