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Volume 69 
Part 5 
Page o693  
May 2013  

Received 31 March 2013
Accepted 4 April 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.134
Data-to-parameter ratio = 28.1
Details
Open access

3-(4-Methoxybenzyl)-1,5-benzothiazepin-4(5H)-one

aDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India,bDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India,cDepartment of Physics, Sri Balaji Chokkalingam Engineering College, Arni, Thiruvannamalai 632 317, India, and dDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
Correspondence e-mail: smurugavel27@gmail.com

In the title compound, C17H15NO2S, the thiazepine ring adopts a slightly distorted twist-boat conformation. The dihedral angle between the mean plane of the benzothiazepin ring system and the benzene ring is 65.7 (1)°. In the crystal, pairs of N-H...O hydrogen bonds link inversion-related molecules into dimers, generating R22(8) ring motifs. These dimers are further linked by C-H...[pi] and [pi]-[pi] interactions [inter-centroid distance between the benzene rings of the benzothiazepine unit = 3.656 (3) Å] into a three-dimensional supramolecular network.

Related literature

For background to the biology of thiazepin derivatives and for a related structure, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15NO2S

  • Mr = 297.36

  • Triclinic, [P \overline 1]

  • a = 7.678 (5) Å

  • b = 9.612 (5) Å

  • c = 10.860 (5) Å

  • [alpha] = 77.208 (5)°

  • [beta] = 74.117 (4)°

  • [gamma] = 81.522 (5)°

  • V = 748.5 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 293 K

  • 0.23 × 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 = 0.951, Tmax = 0.968

  • 18449 measured reflections

  • 5363 independent reflections

  • 3676 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.134

  • S = 1.05

  • 5363 reflections

  • 191 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C3-C7 benzene ring.

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.86 2.02 2.860 (2) 167
C17-H17B...Cgii 0.96 2.96 3.561 (3) 122
Symmetry codes: (i) -x, -y+1, -z; (ii) x+1, y+1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); 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: SJ5315 ).


Acknowledgements

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

References

Bakthadoss, M., Selvakumar, R., Manikandan, N. & Murugavel, S. (2013). Acta Cryst. E69, o562-o563.  [CrossRef] [ChemPort] [details]
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, U. S. A.
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] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o693  [ doi:10.1107/S1600536813009215 ]

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