Received 13 September 2013
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: firstname.lastname@example.org
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-HO interactions, forming a three-dimensional network.
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). For preparation of various heterocycles using imines and T3P, see: Unsworth et al. (2013). For a review of 1,3-thiazin-4-ones, see: Ryabukhin et al. (1996). For other 2,3-diaryl-2,3-dihydro-1,3-benzothiazin-4-ones, see: Kamel et al. (2010); Kollenz & Ziegler (1970); Oae & Numata (1974); Ponci et al. (1963); Zarghi et al. (2009).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XSHELL (Bruker, 2001); software used to prepare material for publication: ORTEP-3 for Windows (Farrugia, 2012).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2105 ).
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.
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