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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 [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.118
Data-to-parameter ratio = 15.0
Details
Open access

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

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 Cc-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 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[Arshad, M. N., Danish, M., Tahir, M. N., Aabideen, Z. U. & Asiri, A. M. (2012). Acta Cryst. E68, o2665.]); Khan et al. (2012[Khan, I. U., Mubashar-ur-Rehman, H., Aziz, S. & Harrison, W. T. A. (2012). Acta Cryst. E68, o2019.]).

[Scheme 1]

Experimental

Crystal data
  • C19H17NO4S

  • Mr = 355.40

  • Monoclinic, P 21 /n

  • a = 8.0694 (2) Å

  • b = 15.2168 (4) Å

  • c = 14.0996 (3) Å

  • [beta] = 92.505 (2)°

  • V = 1729.64 (7) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 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[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.784, Tmax = 1.000

  • 13588 measured reflections

  • 3486 independent reflections

  • 2813 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

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)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]).


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.  [CSD] [CrossRef] [details]
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Khan, I. U., Mubashar-ur-Rehman, H., Aziz, S. & Harrison, W. T. A. (2012). Acta Cryst. E68, o2019.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o194  [ doi:10.1107/S1600536813000081 ]

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