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Volume 69 
Part 11 
Page o1679  
November 2013  

Received 13 September 2013
Accepted 15 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.034
wR = 0.088
Data-to-parameter ratio = 12.4
Details
Open access

2-(3-Nitro­phen­yl)-3-phenyl-2,3-di­hydro-4H-1,3-benzo­thia­zin-4-one

aDepartment of Chemistry, Pennsylvania State University, University Park, PA 16802, USA,bPennsylvania State University, Schuylkill Campus, 200 University Drive, Schuylkill Haven, PA 17972, USA, and cPennsylvania State University, Brandywine Campus, 312 M Main Building, 25 Yearsley Mill Rd., Media, PA 19063, USA
Correspondence e-mail: ljs43@psu.edu

The title compound, C20H14N2O3S, has three aromatic rings, viz. (i) a phenyl ring, (ii) a 3-nitro­phenyl and (iii) a 1,3-benzo­thia­zine fused-ring system. The dihedral angle between (i) and (ii) is 85.31 (15)°, between (ii) and (iii) is 81.33 (15)° and between (i) and (iii) is 75.73 (15)°. The six-membered 1,3-thia­zine ring has an envelope conformation with the C atom in the 2-position forming the flap. In the crystal, mol­ecules are linked by weak C-H...O inter­actions, forming 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 a review of 1,3-thia­zin-4-ones, see: Ryabukhin et al. (1996[Ryabukhin, Y. I., Korzhavina, O. B. & Suzdalev, K. F. (1996). Adv. Heterocycl. Chem. 66, 131-191.]). For other 2,3-diaryl-2,3-di­hydro-1,3-benzo­thia­zin-4-ones, see: Kamel et al. (2010[Kamel, M. M., Ali, H. I., Anwar, M. M., Mohamed, N. A. & Soliman, A. M. M. (2010). Eur. J. Med. Chem. 45, 572-580.]); Kollenz & Ziegler (1970[Kollenz, G. & Ziegler, E. (1970). Monatsh. Chem. 101, 97-101.]); Oae & Numata (1974[Oae, S. & Numata, T. (1974). Tetrahedron, 30, 2641-2646.]); Ponci et al. (1963[Ponci, R., Baruffini, A. & Gialdi, F. (1963). Farmaco, Ed. Sci. 18, 653-657.]); Zarghi et al. (2009[Zarghi, A., Zebardast, T., Daraie, B. & Hedayati, M. (2009). Bioorg. Med. Chem. 17, 5369-5373.]).

[Scheme 1]

Experimental

Crystal data
  • C20H14N2O3S

  • Mr = 362.39

  • Monoclinic, P 21 /n

  • a = 9.8741 (13) Å

  • b = 13.0544 (18) Å

  • c = 13.365 (2) Å

  • [beta] = 100.878 (4)°

  • V = 1691.7 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 298 K

  • 0.27 × 0.25 × 0.24 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT, SADABS and XSHELL. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.945, Tmax = 0.951

  • 9929 measured reflections

  • 2904 independent reflections

  • 2578 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.088

  • S = 1.04

  • 2904 reflections

  • 235 parameters

  • H-atom parameters not refined

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -2.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C19-H19...O3i 0.93 2.67 3.334 (8) 129
C7-H7...O2ii 0.98 2.58 3.424 (8) 145
C11-H11...O3iii 0.93 2.71 3.362 (6) 128
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2105 ).


Acknowledgements

We acknowledge NSF funding (CHEM-0131112) for the X-ray diffractometer. We also express gratitude to Euticals for the gift of T3P in 2-methyl­tetra­hydro­furan.

References

Bruker (2001). SMART, SAINT, SADABS and XSHELL. 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]
Kamel, M. M., Ali, H. I., Anwar, M. M., Mohamed, N. A. & Soliman, A. M. M. (2010). Eur. J. Med. Chem. 45, 572-580.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Kollenz, G. & Ziegler, E. (1970). Monatsh. Chem. 101, 97-101.  [CrossRef] [ChemPort]
Oae, S. & Numata, T. (1974). Tetrahedron, 30, 2641-2646.  [CrossRef] [ChemPort] [Web of Science]
Ponci, R., Baruffini, A. & Gialdi, F. (1963). Farmaco, Ed. Sci. 18, 653-657.
Ryabukhin, Y. I., Korzhavina, O. B. & Suzdalev, K. F. (1996). Adv. Heterocycl. Chem. 66, 131-191.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Unsworth, W. P., Kitsiou, C. & Taylor, R. J. K. (2013). Org. Lett. 15, 258-261.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Zarghi, A., Zebardast, T., Daraie, B. & Hedayati, M. (2009). Bioorg. Med. Chem. 17, 5369-5373.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1679  [ doi:10.1107/S1600536813028389 ]

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