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Volume 69 
Part 4 
Page o564  
April 2013  

Received 16 March 2013
Accepted 18 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.123
Data-to-parameter ratio = 27.5
Details
Open access

(Z)-3-(2,4-Dichlorobenzyl)-1,5-benzothiazepin-4(5H)-one

aDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India,bDepartment of Physics, Bharathidasan Engineering College, Nattrampalli, Vellore 635 854, India, and cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: smurugavel27@gmail.com

In the title compound, C16H11Cl2NOS, the seven-membered thiazepine ring adopts a distorted twist-boat conformation. The dihedral angle between the mean plane of the benzothiazepine ring system and the benzene ring is 78.6 (1)°. The molecular conformation is stabilized by a weak intramolecular C-H...Cl hydrogen bond, which generates an S(5) ring motif. In the crystal, pairs of N-H...O hydrogen bonds link inversion-related molecules into dimers, generating R22(8) ring motifs. The crystal packing also features alternating [pi]-[pi] interactions between benzothiazepine benzene rings [inter-centroid distance = 3.740 (3) Å] and dichlorobenzene rings [inter-centroid distance = 3.882 (3) Å] to consolidate a three-dimensional architecture.

Related literature

For background to the biology and related structures of thiazepin derivatives, see: Bakthadoss et al. (2013[Bakthadoss, M., Selvakumar, R., Manikandan, N. & Murugavel, S. (2013). Acta Cryst. E69, o562-o563.]). For ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). 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
  • C16H11Cl2NOS

  • Mr = 336.22

  • Triclinic, [P \overline 1]

  • a = 7.879 (5) Å

  • b = 9.667 (5) Å

  • c = 9.979 (5) Å

  • [alpha] = 89.052 (5)°

  • [beta] = 78.161 (4)°

  • [gamma] = 83.647 (5)°

  • V = 739.3 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.58 mm-1

  • T = 293 K

  • 0.24 × 0.21 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.871, Tmax = 0.917

  • 18415 measured reflections

  • 5225 independent reflections

  • 4013 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.123

  • S = 1.04

  • 5225 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10B...Cl1 0.97 2.64 3.103 (3) 109
N1-H1A...O1i 0.86 2.10 2.873 (2) 149
Symmetry code: (i) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5208 ).


Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for the data collection.

References

Bakthadoss, M., Selvakumar, R., Manikandan, N. & Murugavel, S. (2013). Acta Cryst. E69, o562-o563.  [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
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, o564  [ doi:10.1107/S1600536813007435 ]

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