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Volume 69 
Part 11 
Page o1608  
November 2013  

Received 16 September 2013
Accepted 19 September 2013
Online 5 October 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.047
wR = 0.134
Data-to-parameter ratio = 12.7
Details
Open access

2-(4-Fluoro­phen­yl)-4-(thio­phen-2-yl)-2,3-di­hydro-1,5-benzothia­zepine

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore, 570 006, India, and bPost Graduate Department of Chemistry, Yuvaraja's College, University of Mysore, Mysore, 570 006, India
Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

In the title compound, C19H14FNS2, the seven-membered thia­zepine ring adopts a slightly distorted twist boat conformation. The dihedral angle between the benzene rings is 53.6 (1)°. The mean plane of the thia­zepine ring is twisted by 34.3 (7)° and 36.6 (7)° from the benezene rings. A C-H...F interaction generates stacking of molecules along the ab plane.

Related literature

For heterocycles containing the 1,4-thia­zepine ring used as pharmaceutical agents as well as for biologically active compounds, see: Shi et al. (2012[Shi, F., Zeng, X.-N., Cao, X.-D., Zhang, S., Jiang, B., Zheng, W.-F. & Tu, S.-J. (2012). Bioorg. Med. Chem. Lett. 22, 743-746.]). For the pharmacological activity of benzo­thia­zepine and its derivatives, see: Sanjeeva et al. (2008[Sanjeeva, R. C., Purnachandra, R. G., Nagaraj, A. & Srinivas, A. (2008). Org. Commun. 1, 84-94.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Bramer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C19H14FNS2

  • Mr = 339.43

  • Monoclinic, C 2/c

  • a = 26.1463 (17) Å

  • b = 12.3091 (8) Å

  • c = 10.1776 (7) Å

  • [beta] = 101.383 (4)°

  • V = 3211.1 (4) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 3.07 mm-1

  • T = 293 K

  • 0.24 × 0.22 × 0.16 mm

Data collection
  • Bruker X8 Proteum diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). SMART, APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.502, Tmax = 0.612

  • 11355 measured reflections

  • 2647 independent reflections

  • 2037 reflections with I > 2[sigma](I)

  • Rint = 0.054

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

  • wR(F2) = 0.134

  • S = 1.05

  • 2647 reflections

  • 209 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C18-H18...F1i 0.93 2.72 3.322 (4) 123
Symmetry code: (i) [x, -y+1, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2013[Bruker (2013). SMART, APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). SMART, APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2176 ).


Acknowledgements

The authors thank the IOE and the University of Mysore for providing the single crystal X-ray diffractometer facility.

References

Allen, F. H., Kennard, O., Watson, D. G., Bramer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans 2, pp. S1-19.
Bruker (2013). SMART, APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sanjeeva, R. C., Purnachandra, R. G., Nagaraj, A. & Srinivas, A. (2008). Org. Commun. 1, 84-94.
Shi, F., Zeng, X.-N., Cao, X.-D., Zhang, S., Jiang, B., Zheng, W.-F. & Tu, S.-J. (2012). Bioorg. Med. Chem. Lett. 22, 743-746.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1608  [ doi:10.1107/S1600536813025889 ]

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