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Volume 69 
Part 11 
Page o1659  
November 2013  

Received 3 September 2013
Accepted 11 October 2013
Online 19 October 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.134
Data-to-parameter ratio = 17.9
Details
Open access

6,7-Diphenyl-5-thia-7-aza­spiro­[2.6]nonan-8-one

aDepartment of Chemistry, Pennsylvania State University, University Park, PA 16802, USA, and bPenn State University, Schuylkill Campus, 200 University Drive, Schuylkill Haven, PA 17972, USA
Correspondence e-mail: ljs43@psu.edu

The asymmetric unit of the title compound, C19H19NOS, contains two independent mol­ecules (A and B), in both of which the 1,3-thia­zepan-4-one ring adopts a chair-type conformation. The dihedral angles between the two phenyl rings are 65.28 (8) and 60.31 (9)° for mol­ecules A and B, respectively. In the crystal, mol­ecules are linked by weak C-H...O inter­actions, resulting in a three-dimensional network.

Related literature

For amide bond formation using 2,4,6-tripropyl-1,3,5,2,4,6-trioxatri­phospho­rinane-2,4,6-trioxide (T3P), see: Dunetz et al. (2011[Dunetz, J. R., Xiang, Y., Baldwin, A. & Ringling, J. (2011). Org. Lett. 13, 5048-5051.]). For preparation of various heterocycles using imines and T3P, see: Unsworth et al. (2013[Unsworth, W. P., Kitsiou, C. & Taylor, R. J. K. (2013). Org. Lett. 15, 258-261.]). For omapatrilat, see: Graul et al. (1999[Graul, A., Leeson, P. & Castañer, J. (1999). Drugs Future, 24, 269-277.]); Robl et al. (1997[Robl, J. A., et al. (1997). J. Med. Chem. 40, 1570-1577.]); Tabrizchi (2001[Tabrizchi, R. (2001). Curr. Opin. Investig. Drugs, 2, 1414-1422.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19NOS

  • Mr = 309.41

  • Triclinic, [P \overline 1]

  • a = 9.9954 (18) Å

  • b = 10.695 (2) Å

  • c = 16.397 (3) Å

  • [alpha] = 79.764 (3)°

  • [beta] = 83.659 (3)°

  • [gamma] = 73.048 (3)°

  • V = 1646.8 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 298 K

  • 0.29 × 0.28 × 0.12 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.559, Tmax = 1.000

  • 14502 measured reflections

  • 7089 independent reflections

  • 5751 reflections with I > 2[sigma](I)

  • Rint = 0.017

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

  • wR(F2) = 0.134

  • S = 1.02

  • 7089 reflections

  • 397 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C18-H18A...O2i 0.97 2.60 3.364 (2) 136
C38-H38A...O1 0.97 2.53 3.384 (2) 146
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2001[Bruker (2001). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SADABS, SAINT and SMART. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2289 ).


Acknowledgements

We acknowledge NSF funding (CHEM-0131112) for the X-ray diffractometer. We also express gratitude to Oakwood Products, Inc. for the gift of [1-(sulfanylmeth­yl)cyclo­prop­yl]acetic acid, and to Euticals for the gift of T3P in 2-methyl­tetra­hydro­furan.

References

Bruker (2001). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Dunetz, J. R., Xiang, Y., Baldwin, A. & Ringling, J. (2011). Org. Lett. 13, 5048-5051.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Graul, A., Leeson, P. & Castañer, J. (1999). Drugs Future, 24, 269-277.  [CrossRef] [ChemPort]
Robl, J. A., et al. (1997). J. Med. Chem. 40, 1570-1577.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Tabrizchi, R. (2001). Curr. Opin. Investig. Drugs, 2, 1414-1422.  [PubMed] [ChemPort]
Unsworth, W. P., Kitsiou, C. & Taylor, R. J. K. (2013). Org. Lett. 15, 258-261.  [Web of Science] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1659  [ doi:10.1107/S1600536813027979 ]

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