Crystal structures of 2-(4-nitro­phen­yl)-3-phenyl-2,3-di­hydro-4H-1,3-benzo­thia­zin-4-one and 2-(2-nitro­phen­yl)-3-phenyl-2,3-di­hydro-4H-1,3-benzo­thia­zin-4-one

Acta Crystallographica Section E: Crystallographic Communications

Yennawar, H.¹  Silverberg, L.J.²  Xie, Y.²  Cali, A.S.² 

[1] Department of Chemistry, Pennsylvania State University, University Park, PA 16802, USA;Pennsylvania State University, Schuylkill Campus, 200 University Drive, Schuylkill Haven, PA 17972, USA

关键词: CRYSTAL STRUCTURE;    BENZOTHIAZINE;    SCREW-BOAT PUCKER;    NITRO-GROUP INTERACTIONS;    HYDROGEN BONDING;    C-H...[PI] INTERACTIONS;   

DOI  :  10.1107/S2056989015004545

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

The crystal structures are reported of the isomeric compounds 2-(4-nitro­phen­yl)-3-phenyl-2,3-di­hydro-4H-1,3-benzo­thia­zin-4-one, (I), and 2-(2-nitro­phen­yl)-3-phenyl-2,3-di­hydro-4H-1,3-benzo­thia­zin-4-one, (II), both C20H14N2O3S, being the para-nitro and ortho-nitro forms, respectively, the meta-form of which is known [Yennawar et al. (2013). Acta Cryst. E69, o1679]. The six-membered thia­zone ring fused with a benzene ring displays a screw-boat conformation with a total puckering amplitude of 0.627 (1) Å in (I), and a near screw-boat conformation with a total puckering amplitude of 0.600 (1) Å in (II). The dihedral angles between the planes of the substituent nitrophenyl and phenyl and rings with the benzene ring of the parent benzo­thia­zone moiety are 75.93 (5) and 82.61 (5)° [in (I)], and 76.79 (6) and 71.66 (6)° [in (II)]. Weak inter­molecular C—H⋯O hydrogen-bonding inter­actions between aromatic H-atom donors and both a nitro-O atom and a thia­zone O-atom acceptor in (I) and a thia­zone O atom in (II) are present, forming in (I) a centrosymmetric 22-membered cyclic dimer which is extended through a similar inversion-related 14-membered cyclic hydrogen-bonding association into a zigzag chain structure extending along c. In (II), a single inter­molecular C—H⋯O hydrogen bond gives a chain structure extending along b. In addition, weak C—H⋯π inter­actions are present in both structures [minimum C⋯ring-centroid separations = 3.630 (2) and 3.581 (2) Å, respectively].

【 授权许可】

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