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Volume 69 
Part 4 
Pages o562-o563  
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) = 0.003 Å
R = 0.039
wR = 0.121
Data-to-parameter ratio = 14.7
Details
Open access

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

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

In the title compound, C18H17NO3S, the seven-membered thiazepine ring adopts a slightly distorted sofa conformation. The dihedral angle between the mean plane of the benzothiazepine ring system and the benzene ring is 5.9 (1)°. The molecular conformation is stabilized by an intramolecular C-H...S hydrogen bond, which generates an S(7) ring motif. In the crystal, N-H...O and C-H...O hydrogen bonds link inversion-related molecules into dimers, incorporating R12(6) and R22(8) ring motifs; the acceptor O atom is bifurcated. These dimers are further linked by C-H...O hydrogen bonds, forming supramolecular tapes running along the a axis. These are connected into the three-dimensional architecture by C-H...[pi] interactions.

Related literature

For the pharmaceutical properties of thiazepine derivatives, see: Tomascovic et al. (2000[Tomascovic, L. L., Arneri, R. S., Brundic, A. H., Nagl, A., Mintas, M. & Sandtrom, J. (2000). Helv. Chim. Acta, 83, 479-493.]); Rajsner et al. (1971[Rajsner, M., Protiva, M. & Metysova, J. (1971). Czech. Patent Appl. CS 143737.]); Metys et al. (1965[Metys, J., Metysova, J. & Votava, Z. (1965). Acta Biol. Med. Ger. 15, 871-873.]). For related structures, see: Lakshmanan et al. (2012[Lakshmanan, D., Murugavel, S., Selvakumar, R. & Bakthadoss, M. (2012). Acta Cryst. E68, o2130.]); Selvakumar et al. (2012[Selvakumar, R., Bakthadoss, M., Lakshmanan, D. & Murugavel, S. (2012). Acta Cryst. E68, o2126.]); Murugavel et al. (2013[Murugavel, S., Manikandan, N., Selvakumar, R. & Bakthadoss, M. (2013). Acta Cryst. E69, o564.]). 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
  • C18H17NO3S

  • Mr = 327.39

  • Triclinic, [P \overline 1]

  • a = 7.0249 (4) Å

  • b = 10.7949 (7) Å

  • c = 10.8826 (7) Å

  • [alpha] = 91.783 (3)°

  • [beta] = 97.562 (2)°

  • [gamma] = 108.512 (2)°

  • V = 773.42 (8) 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 = 0.950, Tmax = 0.967

  • 14052 measured reflections

  • 3082 independent reflections

  • 2545 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.121

  • S = 1.06

  • 3082 reflections

  • 210 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2-C7 ring.

D-H...A D-H H...A D...A D-H...A
C12-H12...S1 0.93 2.76 3.605 (2) 151
N1-H1...O1i 0.86 2.12 2.967 (2) 170
C6-H6...O1i 0.93 2.52 3.318 (2) 144
C5-H5...O3ii 0.93 2.46 3.377 (3) 167
C17-H17C...Cg1iii 0.96 2.84 3.724 (2) 154
C18-H18A...Cg1iv 0.96 2.90 3.841 (3) 166
Symmetry codes: (i) -x, -y+1, -z+2; (ii) x-2, y-1, z; (iii) -x+1, -y+1, -z+1; (iv) x+1, y+1, z.

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: TK5207 ).


Acknowledgements

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

References

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]
Lakshmanan, D., Murugavel, S., Selvakumar, R. & Bakthadoss, M. (2012). Acta Cryst. E68, o2130.  [CSD] [CrossRef] [details]
Metys, J., Metysova, J. & Votava, Z. (1965). Acta Biol. Med. Ger. 15, 871-873.  [ChemPort] [PubMed]
Murugavel, S., Manikandan, N., Selvakumar, R. & Bakthadoss, M. (2013). Acta Cryst. E69, o564.  [CrossRef] [details]
Rajsner, M., Protiva, M. & Metysova, J. (1971). Czech. Patent Appl. CS 143737.
Selvakumar, R., Bakthadoss, M., Lakshmanan, D. & Murugavel, S. (2012). Acta Cryst. E68, o2126.  [CSD] [CrossRef] [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]
Tomascovic, L. L., Arneri, R. S., Brundic, A. H., Nagl, A., Mintas, M. & Sandtrom, J. (2000). Helv. Chim. Acta, 83, 479-493.


Acta Cryst (2013). E69, o562-o563   [ doi:10.1107/S1600536813007423 ]

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