2-Benzene­sulfonamido-3-methyl­butyric acid

Muhammad Nadeem Arshad; Muhammad Danish; Muhammad Nawaz Tahir; Zain Ul Aabideen; Abdullah M Asiri

doi:10.1107/S1600536812034393

. 2012 Aug 8;68(Pt 9):o2665. doi: 10.1107/S1600536812034393

2-Benzenesulfonamido-3-methylbutyric acid

Muhammad Nadeem Arshad ^a,^*, Muhammad Danish ^b,^*, Muhammad Nawaz Tahir ^c, Zain Ul Aabideen ^b, Abdullah M Asiri ^a,^d

PMCID: PMC3435689 PMID: 22969560

Abstract

In the crystal structure of the title compound, C₁₁H₁₅NO₄S, two independent molecules are present per asymmetric unit; they are dimerized through O—H⋯O hydrogen bonds between their carboxy groups to generate R ₂ ²(8) loops. An intramolecular N—H⋯O link in one of the molecules closes an S(5) ring. The dimers are linked by N—H⋯O and C—H⋯O hydrogen bonds to form a three-dimensional network. The C atoms of the isopropyl group of one of the molecules are disordered over two orientations in a 3:1 ratio.

Related literature

For biological studies of sulfonamides, see: Nalam et al. (2007 ▶). For related structures, see: Khan et al. (2011 ▶); Arshad et al. (2012 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₁H₁₅NO₄S
M _r = 257.30
Monoclinic,
a = 5.4954 (3) Å
b = 15.5097 (10) Å
c = 15.5106 (9) Å
β = 94.043 (3)°
V = 1318.71 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.37 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T _min = 0.914, T _max = 0.957
9573 measured reflections
4203 independent reflections
3803 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.093
S = 1.05
4203 reflections
335 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack (1983 ▶), 1785 Friedel pairs
Flack parameter: 0.00 (6)

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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and X-SEED (Barbour, 2001 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812034393/hb6922sup1.cif

e-68-o2665-sup1.cif^{(33.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034393/hb6922Isup2.hkl

e-68-o2665-Isup2.hkl^{(205.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034393/hb6922Isup3.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
O8—H8O⋯O3	0.85 (1)	1.81 (1)	2.649 (3)	171 (6)
O4—H4O⋯O7	0.86 (1)	1.83 (2)	2.668 (3)	166 (6)
N1—H1N⋯O1ⁱ	0.81 (5)	2.52 (5)	3.322 (3)	172 (5)
N2—H2N⋯O7ⁱ	0.82 (5)	2.47 (5)	3.240 (3)	157 (5)
N2—H2N⋯O8	0.82 (5)	2.45 (5)	2.734 (3)	102 (4)
C2—H2⋯O3ⁱⁱ	0.93	2.56	3.440 (4)	158
C4—H4⋯O6ⁱⁱⁱ	0.93	2.54	3.427 (4)	161
C14—H14⋯O2^iv	0.93	2.52	3.378 (5)	154
C15—H15⋯O1^v	0.93	2.60	3.521 (5)	173
C9A—H9A⋯O2^v	0.98	2.52	3.421 (7)	153

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

Acknowledgments

The authors acknowledge the University of Sargodha for providing diffraction facilities at its Department of Physics.

supplementary crystallographic information

Comment

Crystal structure of sulfonamide derived from lysine has been reported which proved as a new class of inhibitors, to combat the resistant variants of HIV protease (Nalam et al., 2007). Herein, we report the crystal structure of sulfonamide derived from L-valine, in countinuation of our work for the synthesis of sulfonamide (Khan et al., 2011), (Arshad et al., 2012).

The unit cell comprises of two independent molecules (C1—C11) A & (C12—C22) B. Each molecule adopted U shaped and aromatic rings are oriented with carboxylic groups at dihedral angles of 20.91 (2)° & 28.27 (2)° in molecule A and B respectively. These two molecules have been joined to each other through complex intermolecular hydrogen bonding interactions. Molecule B also undergoes intramolecular hydrogen bonding to form five membered (N2/C18/C19/O8/H2N) ring motif S₁¹(5) (Bernstein et al., 1995). Molecules undergo typical dimerization to produce eight membered ring motifs R₂²(8) (Bernstein et al., 1995) through the carboxylic functional groups. This ring motif (O3/C8/O4/H4O/O7/C19/O8/H8O) lies between the two aromatic rings just like sandwich and the centroid distances of plane generated from it are 3.934 Å & 4.155 Å with aromatic rings (C1—C6) & (C12—C17) respectively. These dimers further connected through the N—H···O, O—H···O and C—H···O type interaction to form three dimensional network (Table. 1, Fig. 2). The C- atoms of isopropyl group in molecule A is disordered over two positions with occupancies ratio of 3:1.

Experimental

L-Valine (0.50 g, 0.043 mmole) dissolved in 12-15 mL distilled water using sodium carbonate (1M) to a pH of 8–9. Benzenesulphonyl chloride (0.75 g, 0.043 mmole) added within 3–5 min. The pH was adjusted by sodium carbonate (1M). Disappearance of suspended benzenesulfonyl chloride gave indication of completion of reaction. Then, dilute HCl was added dropwise to result in a pH 2–3. The precipitate was filtered, washed with plenty of water and dried. Colourless prisms were obtained upon recrystalization from methanol solution.