Crystal structures of 2-(4-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one and 2-(2-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one.

ABSTRACT: The crystal structures are reported of the isomeric compounds 2-(4-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one, (I), and 2-(2-nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-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 thia-zone 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 benzo-thia-zone moiety are 75.93?(5) and 82.61?(5)° [in (I)], and 76.79?(6) and 71.66?(6)° [in (II)]. Weak inter-molecular C-H?O hydrogen-bonding inter-actions between aromatic H-atom donors and both a nitro-O atom and a thia-zone O-atom acceptor in (I) and a thia-zone 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 inter-molecular C-H?O hydrogen bond gives a chain structure extending along b. In addition, weak C-H?? inter-actions are present in both structures [minimum C?ring-centroid separations = 3.630?(2) and 3.581?(2)?Å, respectively].

SUBMITTER: Yennawar H 

PROVIDER: S-EPMC4438845 | biostudies-other | 2015 Apr

REPOSITORIES: biostudies-other