(2R)-2-Benzene­sulfonamido-2-phenyl­ethanoic acid

Muhammad Nadeem Arshad; M Nawaz Tahir; Islam Ullah Khan; Muhammad Shafiq; Sarfraz Ahmad

doi:10.1107/S1600536809011611

. 2009 Apr 2;65(Pt 5):o940. doi: 10.1107/S1600536809011611

(2R)-2-Benzenesulfonamido-2-phenylethanoic acid

Muhammad Nadeem Arshad ^a, M Nawaz Tahir ^b,^*, Islam Ullah Khan ^a, Muhammad Shafiq ^a, Sarfraz Ahmad ^c

PMCID: PMC2977641 PMID: 21583984

Abstract

In the title compound, C₁₄H₁₃NO₄S, the dihedral angle between the aromatic ring planes is 45.52 (18)°. In the crystal structure, intermolecular N—H⋯O and O—H⋯O hydrogen bonds lead to chains of molecules propagating in [100] in which the the ring motifs R ₂ ¹(8), R ₂ ²(8) and R ₃ ³(11) are apparent. These polymeric chains are linked through C—H⋯O interactions.

Related literature

For related structures, see: Chaudhuri (1984 ▶); Shan & Huang (1999 ▶). For background, see: Arshad et al. (2008 ▶); Cama et al. (2003 ▶); Dankwardt et al. (2002 ▶); Zhi-jian et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₃NO₄S
M _r = 291.31
Orthorhombic,
a = 5.6022 (5) Å
b = 12.5026 (9) Å
c = 19.7886 (15) Å
V = 1386.03 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.22 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.944, T _max = 0.966
8476 measured reflections
2818 independent reflections
1679 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.091
S = 1.01
2818 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ▶), 1092 Friedal Pairs
Flack parameter: 0.02 (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 datablocks global, I. DOI: 10.1107/S1600536809011611/hb2938sup1.cif

e-65-0o940-sup1.cif^{(18KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011611/hb2938Isup2.hkl

e-65-0o940-Isup2.hkl^{(135.5KB, hkl)}

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	2.55	3.155 (4)	128
O3—H3O⋯O4ⁱⁱ	0.82	1.83	2.646 (3)	176
C2—H2⋯O1ⁱⁱⁱ	0.93	2.56	3.340 (5)	142
C3—H3⋯O2^iv	0.93	2.54	3.225 (5)	131
C7—H7⋯O1ⁱⁱⁱ	0.98	2.55	3.432 (4)	150

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

Acknowledgments

MNA greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him with a Scholaship under the Indigenous PhD Program (PIN 042–120607-PS2-183).

supplementary crystallographic information

Comment

Amino acid derived sulfonamides have been synthesized as ligands (Zhi-jian et al., 2006) which showed potent procollagen C-proteinase (PCP) inhibition (Dankwardt et al., 2002) and arginase inhibition (Cama et al., 2003). The title compound (I), (Fig 1), has been prepared as an intermediate for the synthesis of our ongoing studies of thiazine (Arshad et al., 2008) related heterocycles.

The crystal structure of (II) R-(-)-N-benzenesulfonylglutamic acid (Shan & Huang, 1999) and (III) N-Benzenesulfonyl-DL-alanine (Chaudhuri, 1984) have been published. These structures have a common group with (I) except the benzene ring of phenyl glycine.

The title compound has a chairal center at C7 with slightly distorted tetrahedral geometry with H7 at the apical position. The coordination around the S-atom is distorted tetrahedral. The molecules of the compound are stabilized due to strong intermolecular H-bonding (Table 1). Three ring motifs R₂¹(8), R₂²(8) and R₃³(11) (Bernstein et al., 1995) are formed due to two H-bonds of C—H···O type, H-bonding of types C—H···O and N—H···O, and two O—H···O and N—H···O, respectively (Fig 2). The ring motifs are connected to each other in such a way that a rod-shaped attachement of molecules exist along the a axis. These polymeric chains are linked through the remaing H-bonding of C—H···O type.

Experimental

Phenyl glycine (1 g, 6.6 mmol) was dissolved in distilled water (10 ml) in a round bottom flask (25 ml). The pH of the solution was maintained at 8–9 using 1M, Na₂CO₃ solution. Benzene sulfonyl chloride (1.16 g, 6.6 mmol) was then added to the solution and stirred at room temperature until all the benzene sulfonyl chloride was consumed. On completion of the reaction the pH was adjusted 1–2, using 1 N HCl. The precipitate obtained was filtered, washed with distilled water, dried and recrystalized in dichloromethane and methanol to yield colourless prisms of (I).