2-(Naphthalene-2-sulfonamido)-3-phenyl­propanoic acid

Hafiz Mubashar-ur-Rehman; Muhammad Nadeem Arshad; Abdullah M Asiri; Islam Ullah Khan; Muhammad Bilal

doi:10.1107/S1600536813000081

. 2013 Jan 9;69(Pt 2):o194. doi: 10.1107/S1600536813000081

2-(Naphthalene-2-sulfonamido)-3-phenylpropanoic acid

Hafiz Mubashar-ur-Rehman ^a,^*, Muhammad Nadeem Arshad ^b,^*, Abdullah M Asiri ^c,^b, Islam Ullah Khan ^a, Muhammad Bilal ^d

PMCID: PMC3569255 PMID: 23424478

Abstract

In the title compound, C₁₉H₁₇NO₄S, the phenyl ring and the naphthalene ring system are oriented at a dihedral angle of 4.12 (2)° and the molecule adopts a U-shaped conformation. The C_c—C—N—S (c = carboxy) torsion angle is 90.98 (15)°. In the crystal, molecules are linked by O—H⋯O and N—H⋯O hydrogen bonds, resulting in (100) chains incorporating centrosymmetric R ² ₂(14) and R ² ₂(10) loops. Weak aromatic π–π stacking is also observed [centroid–centroid separations = 3.963 (2) and 3.932 (2) Å].

Related literature

For the synthesis and related structures, see: Arshad et al. (2012 ▶); Khan et al. (2012 ▶).

Experimental

Crystal data

C₁₉H₁₇NO₄S
M _r = 355.40
Monoclinic,
a = 8.0694 (2) Å
b = 15.2168 (4) Å
c = 14.0996 (3) Å
β = 92.505 (2)°
V = 1729.64 (7) Å³
Z = 4
Cu Kα radiation
μ = 1.87 mm⁻¹
T = 296 K
0.29 × 0.10 × 0.09 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) CCD diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.784, T _max = 1.000
13588 measured reflections
3486 independent reflections
2813 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.118
S = 1.03
3486 reflections
232 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▶) and X-SEED (Barbour, 2001 ▶).

Supplementary Material

Click here for additional data file.^{(24.7KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000081/hb7020sup1.cif

e-69-0o194-sup1.cif^{(24.7KB, cif)}

Click here for additional data file.^{(171KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000081/hb7020Isup2.hkl

e-69-0o194-Isup2.hkl^{(171KB, hkl)}

Click here for additional data file.^{(6.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813000081/hb7020Isup3.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⋯O3ⁱ	0.80 (2)	2.18 (2)	2.964 (2)	164 (2)
O4—H1O⋯O2ⁱⁱ	0.88 (3)	1.90 (3)	2.772 (2)	174 (2)

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

Acknowledgments

The authors thank the Deanship of Scientific Research at King Abdulaziz University for the support of this research via Research Group Track grant No. 3-102/428.

supplementary crystallographic information

Comment

In countinuation of our studies of the synthesis of sulfonamide derivatives of amino acids (Khan et al., 2012) & (Arshad et al., 2012) we now report the crystal structure of title compound.

In the structure of molecule the naphthalene and benzene rings are almost parallel, since the dihedral angle is as small as 4.12 (2)°. The sulfur (S1) atom as usual adopted the distorted tetrahedral geometry with O1-S1-O2 angle of 118.96 (9)°. The O—H···O type intermolecular hudrogen bonding connects the molecules to form inversion dimers and resulting in fourteen R²₂(14) membered ring motifs. On the othe other hand, these dimers connected through another N—H···O type link to give ten R²₂(10) membered ring motif and generates a long chain along the a axis direction (Table. 1, Fig. 2). The presence of π-π stacking interactions between aromatic rings is also observed: Cg1-Cg2 (Cg1: C1-C6; Cg2: C5-C10) with distances of 3.963 (2) Å (1 - x, 1 - y, 2 - z) and Cg2-Cg2 with distances of 3.932 (2) Å (1 - x, 1 -y , 2 - z).

Experimental

The title compound was synthesised following the literature method (Arshad et al., 2012) and recrystallized from methanol solution as colourless prisms by slow evaporation at room temperature.