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Volume 69 
Part 12 
Pages o1750-o1751  
December 2013  

Received 21 October 2013
Accepted 31 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.135
Data-to-parameter ratio = 21.0
Details
Open access

N-(4-Acetyl­phen­yl)-4-meth­oxy­benzene­sulfonamide

aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: suchada.c@psu.ac.th

The title compound, C15H15NO4S, was obtained by the condensation of 4-amino­aceto­phenone and 4-meth­oxy­benzene­sulfonyl chloride. The dihedral angle between the benzene rings is 86.56 (9)° and the mol­ecule has an approximate V-shaped conformation. The C atom of the meth­oxy group is roughly coplanar with its attached ring [deviation = 0.177 (3) Å], as is the methyl C atom of the acetyl group with its ring [deviation = 0.065 (2) Å]. An intra­molecular C-H...O inter­action generates an S(6) ring. In the crystal, N-H...O and C-H...O hydrogen bonds link the mol­ecules into [010] chains. Weak C-H...[pi] inter­actions are also observed.

Related literature

For related structures, see: Li et al. (2006[Li, X.-M., Zeng, C.-C., Xu, Y.-S., Yan, H., Zheng, D.-W. & Zhong, R. G. (2006). J. Chem. Crystallogr. 36, 357-363.]); Xu et al. (2005[Xu, Y.-S., Zeng, C.-C., Li, X.-M. & Zhong, R.-G. (2005). Acta Cryst. E61, o3802-o3804.]). For background to and applications of sulfonamides, see: Alsughayer et al. (2011[Alsughayer, A., Elassar, A.-Z. A., Mustafa, S. & Sagheer, F. A. (2011). J. Biomater. Nanobiotechnol. 2, 144-149.]); Dragostin et al. (2013[Dragostin, O. M., Lupascu, F., Vasile, C., Mares, M., Nastasa, V., Moraru, R. F., Pieptu, D. & Profire, L. (2013). Molecules, 18, 4140-4157.]);

[Scheme 1]

Experimental

Crystal data
  • C15H15NO4S

  • Mr = 305.35

  • Monoclinic, P 21 /c

  • a = 12.8220 (3) Å

  • b = 8.2709 (2) Å

  • c = 14.6165 (4) Å

  • [beta] = 112.841 (1)°

  • V = 1428.52 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 298 K

  • 0.48 × 0.44 × 0.33 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.894, Tmax = 0.924

  • 15571 measured reflections

  • 4120 independent reflections

  • 2593 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.135

  • S = 1.04

  • 4120 reflections

  • 196 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C7-C12 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O3i 0.85 (2) 2.05 (2) 2.896 (2) 172.3 (19)
C8-H8A...O2 0.93 2.38 3.030 (2) 127
C9-H9A...O1ii 0.93 2.53 3.459 (2) 174
C14-H14A...Cg1i 0.96 2.83 3.630 (3) 141
C14-H14C...Cg2iii 0.96 2.83 3.529 (2) 130
C15-H15C...Cg1iv 0.96 2.99 3.804 (3) 144
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) -x+1, -y+1, -z+2; (iv) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]), Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7153 ).


Acknowledgements

Financial support from the Thailand Research Fund through the Royal Golden Jubilee PhD Program (grant No. PHD/0137/2554) is gratefully acknowledged. CSCK thanks the Universiti Sains Malaysia for a postdoctoral research fellowship. The authors extend their appreciation to Prince of Songkla University and the Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.

References

Alsughayer, A., Elassar, A.-Z. A., Mustafa, S. & Sagheer, F. A. (2011). J. Biomater. Nanobiotechnol. 2, 144-149.  [CrossRef] [ChemPort]
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dragostin, O. M., Lupascu, F., Vasile, C., Mares, M., Nastasa, V., Moraru, R. F., Pieptu, D. & Profire, L. (2013). Molecules, 18, 4140-4157.  [CrossRef] [ChemPort] [PubMed]
Li, X.-M., Zeng, C.-C., Xu, Y.-S., Yan, H., Zheng, D.-W. & Zhong, R. G. (2006). J. Chem. Crystallogr. 36, 357-363.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Xu, Y.-S., Zeng, C.-C., Li, X.-M. & Zhong, R.-G. (2005). Acta Cryst. E61, o3802-o3804.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1750-o1751   [ doi:10.1107/S1600536813029875 ]

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