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Volume 69 
Part 7 
Page o1129  
July 2013  

Received 7 May 2013
Accepted 14 May 2013
Online 19 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.006 Å
R = 0.050
wR = 0.187
Data-to-parameter ratio = 22.1
Details
Open access

7-Bromo-3,3-dibutyl-8-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

aDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysore 570 006, India,bDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and cDepartment of Studies in Microbiology, Manasagangotri, University of Mysore, Mysore 570 006, India
Correspondence e-mail: bhadre_chem@rediffmail.com

In the title compound C18H26BrNO2S, the thiazepine ring adopts a boat conformation. The dihedral angle between the mean planes through the benzene ring and the four C atoms making up the basal plane of the boat is 35.8 (2)°. In the crystal, inversion dimers linked by pairs of N-H...O hydrogen bonds generate R22(8) loops.

Related literature

For reference bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For background to the uses of this class of compounds, see: Fedi et al. (2008[Fedi, V., Guidi, A. & Altamura, M. (2008). Mini Rev. Med. Chem. 8, 1464-1484.]); Ganesh et al. (2011[Ganesh, D. M., Yogesh, M. K., Ashok, K., Dharmendra, S., Kisan, M. K. & Suresh, B. M. (2011). Indian J. Chem. Sect. B, 50, 1197-1201.]); Riedel et al. (2007[Riedel, M., Mueller, N., Strassnig, M., Spellman, I., Severus, E. & Moeller, H. J. (2007). Neuropsy. Dis. Treat. 3, 219-235.]).

[Scheme 1]

Experimental

Crystal data
  • C18H26BrNO2S

  • Mr = 400.30

  • Monoclinic, P 21 /n

  • a = 7.7844 (18) Å

  • b = 11.251 (2) Å

  • c = 22.039 (6) Å

  • [beta] = 98.199 (8)°

  • V = 1910.5 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.27 mm-1

  • T = 100 K

  • 0.32 × 0.20 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • 16056 measured reflections

  • 4662 independent reflections

  • 2750 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.141

  • S = 1.03

  • 4662 reflections

  • 212 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.63 e Å-3

  • [Delta][rho]min = -0.49 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N14-H14...O15i 0.86 2.13 2.985 (3) 175
Symmetry code: (i) -x+1, -y+1, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: Mercury.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7081 ).


Acknowledgements

MM thanks the IOE and the University of Mysore for the award of a fellowship and research grants. The data collection was performed at the Solid Sate and Structural Chemistry Unit, IISC.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Fedi, V., Guidi, A. & Altamura, M. (2008). Mini Rev. Med. Chem. 8, 1464-1484.  [CrossRef] [PubMed] [ChemPort]
Ganesh, D. M., Yogesh, M. K., Ashok, K., Dharmendra, S., Kisan, M. K. & Suresh, B. M. (2011). Indian J. Chem. Sect. B, 50, 1197-1201.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Riedel, M., Mueller, N., Strassnig, M., Spellman, I., Severus, E. & Moeller, H. J. (2007). Neuropsy. Dis. Treat. 3, 219-235.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1129  [ doi:10.1107/S1600536813013238 ]

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