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Volume 69 
Part 11 
Page o1716  
November 2013  

Received 16 October 2013
Accepted 22 October 2013
Online 31 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.052
wR = 0.163
Data-to-parameter ratio = 25.1
Details
Open access

N-[(2-Chloro­phen­yl)sulfon­yl]-2-meth­oxy­benzamide

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,bDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India,cUniversity College of Science, Tumkur University, Tumkur 572 103, Karnataka, India,dDepartment of Physics, Karnatak University, Dharwad, Karnataka 580 003, India, and eDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
Correspondence e-mail: pasuchetan@yahoo.co.in

The title compound, C14H12ClNO4S, crystallizes with two mol­ecules in the asymmetric unit. The dihedral angles between the benzene rings are 89.68 (1) (mol­ecule 1) and 82.9 (1)° (mol­ecule 2). In each mol­ecule, intra­molecular N-H...O hydrogen bonds between the amide H atom and the meth­oxy O atom generate S(6) loops. In the crystal, mol­ecule 2 is linked into inversion dimers through pairs of C-H...O inter­actions, forming an R22(8) ring motif. Mol­ecules 1 and 2 are further linked along the b-axis direction through C-H...[pi] inter­actions. The crystal structure is further stabilized by several [pi]-[pi] stacking inter­actions [centroid-centroid separations = 3.7793 (1), 3.6697 (1) and 3.6958 (1) Å], thus generating a three-dimensional architecture.

Related literature

For similar structures, see: Gowda et al. (2010[Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o794.]); Suchetan et al. (2010a[Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o1040.],b[Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o1281.], 2013[Suchetan, P. A., Palakshamurthy, B. S., Mamatha, G. R., Kumar, V., Mohan, N. R. & Sreenivasa, S. (2013). Acta Cryst. E69, o1215.]). For hydrogen-bond motifs see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12ClNO4S

  • Mr = 325.76

  • Triclinic, [P \overline 1]

  • a = 8.0508 (3) Å

  • b = 12.9487 (4) Å

  • c = 14.1915 (5) Å

  • [alpha] = 83.897 (2)°

  • [beta] = 89.368 (2)°

  • [gamma] = 89.704 (2)°

  • V = 1470.94 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.42 mm-1

  • T = 293 K

  • 0.36 × 0.29 × 0.23 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 34023 measured reflections

  • 9760 independent reflections

  • 6518 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.163

  • S = 0.90

  • 9760 reflections

  • 389 parameters

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

  • [Delta][rho]max = 0.68 e Å-3

  • [Delta][rho]min = -0.59 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C22-C27 ring.

D-H...A D-H H...A D...A D-H...A
N1-HN1...O4 0.84 (2) 1.97 (2) 2.625 (2) 135 (2)
N2-HN2...O8 0.83 (2) 1.99 (2) 2.629 (3) 133 (2)
C13-H13...O3i 0.93 2.50 3.292 (3) 143
C10-H10...Cg 0.93 2.85 3.729 (3) 157
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5359 ).


Acknowledgements

PAS thanks the University Grants Commission (UGC), India, for financial support under its Minor Research Project scheme. JT thanks the Department of Science and Technology (DST), New Delhi, for the SCXRD facility under the PURSE Grant (SR/S9/Z-23/2008/11, 2009) at USIC, Karnatak University.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2009). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o794.  [CrossRef] [IUCr Journals]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010a). Acta Cryst. E66, o1040.  [CSD] [CrossRef] [IUCr Journals]
Suchetan, P. A., Gowda, B. T., Foro, S. & Fuess, H. (2010b). Acta Cryst. E66, o1281.  [CrossRef] [IUCr Journals]
Suchetan, P. A., Palakshamurthy, B. S., Mamatha, G. R., Kumar, V., Mohan, N. R. & Sreenivasa, S. (2013). Acta Cryst. E69, o1215.  [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1716  [ doi:10.1107/S1600536813029012 ]

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