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

Mubashar-ur-Rehman, H.; Arshad, M.N.; Asiri, A.M.; Khan, I.U.; Bilal, M.

doi:10.1107/S1600536813000081

Volume 69
Part 2
Page o194
February 2013

Received 23 December 2012
Accepted 2 January 2013
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.118
Data-to-parameter ratio = 15.0
Details

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 and Muhammad Bilal ^d

^aDepartment of Chemistry, Materials Chemistry Laboratory, GC University, Lahore 54000, Pakistan,^bCenter of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia,^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and ^dDepartment of Chemistry, University of Engineering & Technology, Lahore 54000, Pakistan
Correspondence e-mail: malikg781@yahoo.com, mnachemist@hotmail.com

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-HO and N-HO hydrogen bonds, resulting in (100) chains incorporating centrosymmetric R²₂(14) and R²₂(10) loops. Weak aromatic [pi] - [pi] 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, P 2₁ /n
a = 8.0694 (2) Å
b = 15.2168 (4) Å
c = 14.0996 (3) Å
= 92.505 (2)°
V = 1729.64 (7) Å³
Z = 4
Cu K radiation
= 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 > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.118
S = 1.03
3486 reflections
232 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO3ⁱ	0.80 (2)	2.18 (2)	2.964 (2)	164 (2)
O4-H1OO2ⁱⁱ	0.88 (3)	1.90 (3)	2.772 (2)	174 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

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 data and figures for this paper are available from the IUCr electronic archives (Reference: HB7020 ).

Acknowledgements

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.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Arshad, M. N., Danish, M., Tahir, M. N., Aabideen, Z. U. & Asiri, A. M. (2012). Acta Cryst. E68, o2665.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Khan, I. U., Mubashar-ur-Rehman, H., Aziz, S. & Harrison, W. T. A. (2012). Acta Cryst. E68, o2019.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds