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Volume 69 
Part 5 
Page o708  
May 2013  

Received 1 April 2013
Accepted 8 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.060
wR = 0.175
Data-to-parameter ratio = 62.7
Details
Open access

(Z)-3-(3,4-Dimethoxybenzyl)-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, C18H17NO3S, 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 60.3 (1)°. In the crystal, molecules are linked by two pairs of inversion-related N-H...O and C-H...O hydrogen bonds, generating alternating R22(8) and R22(6) ring motifs, respectively, in a zigzag supramolecular chain that runs along the c axis. These chains stack along the a axis via S...C [3.424 (2) Å] contacts. A three-dimensional supramolecular network is consolidated by C-H...[pi] and [pi]-[pi] interactions [inter-centroid distance between dimethoxybenzene rings = 3.815 (1) Å]. The crystal studied was a non-merohedral twin, with a refined value of the minor twin fraction of 0.2477 (6) .

Related literature

For background to the biology of thiazepine 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
  • C18H17NO3S

  • Mr = 327.39

  • Orthorhombic, P b c n

  • a = 19.966 (4) Å

  • b = 10.355 (2) Å

  • c = 15.536 (3) Å

  • V = 3212.0 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 293 K

  • 0.35 × 0.20 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (TWINABS; Sheldrick, 1997[Sheldrick, G. M. (1997). TWINABS. University of Göttingen, Germany.]) Tmin = 0.927, Tmax = 0.968

  • 13227 measured reflections

  • 13227 independent reflections

  • 8413 reflections with I > 2[sigma](I)

  • Rint = 0.066

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.175

  • S = 1.02

  • 13227 reflections

  • 211 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C11-C16 and C2-C7 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.86 2.02 2.863 (2) 167
C18-H18B...O3ii 0.96 2.53 3.445 (3) 159
C4-H4...Cg1iii 0.93 2.57 3.450 (2) 158
C10-H10B...Cg2iv 0.97 2.82 3.725 (2) 155
Symmetry codes: (i) -x, -y, -z+2; (ii) -x, -y+1, -z+1; (iii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [x, -y, z-{\script{3\over 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: TK5214 ).


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, 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. (1997). TWINABS. 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, o708  [ doi:10.1107/S1600536813009598 ]

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