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

Hemant P. Yennawar, Aaron S. Cali, Yiwen Xie, Lee Jonathan Silverberg, G. Smith

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Abstract

The crystal structures are reported of the isomeric compounds 2-(4-nitrophen-y1)-3-pheny1-2,3-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].

Original languageEnglish (US)
Pages (from-to)414-417
Number of pages4
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number4
DOIs
StatePublished - Apr 1 2015

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Crystal structure
Atoms
Hydrogen bonds
crystal structure
rings
boats
Boats
screws
Benzene
atoms
Conformations
benzene
Dihedral angle
hydrogen
Dimers
centroids
dihedral angle
dimers
Association reactions
interactions

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

Cite this

@article{8f6e27d0d0f145ee9dc6c61c922d10fc,
title = "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",
abstract = "The crystal structures are reported of the isomeric compounds 2-(4-nitrophen-y1)-3-pheny1-2,3-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) {\AA} in (I), and a near screw-boat conformation with a total puckering amplitude of 0.600 (1) {\AA} 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) {\AA}, respectively].",
author = "Yennawar, {Hemant P.} and Cali, {Aaron S.} and Yiwen Xie and Silverberg, {Lee Jonathan} and G. Smith",
year = "2015",
month = "4",
day = "1",
doi = "10.1107/S2056989015004545",
language = "English (US)",
volume = "71",
pages = "414--417",
journal = "Acta Crystallographica Section E: Structure Reports Online",
issn = "1600-5368",
publisher = "International Union of Crystallography",
number = "4",

}

TY - JOUR

T1 - 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

AU - Yennawar, Hemant P.

AU - Cali, Aaron S.

AU - Xie, Yiwen

AU - Silverberg, Lee Jonathan

AU - Smith, G.

PY - 2015/4/1

Y1 - 2015/4/1

N2 - The crystal structures are reported of the isomeric compounds 2-(4-nitrophen-y1)-3-pheny1-2,3-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].

AB - The crystal structures are reported of the isomeric compounds 2-(4-nitrophen-y1)-3-pheny1-2,3-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].

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U2 - 10.1107/S2056989015004545

DO - 10.1107/S2056989015004545

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JO - Acta Crystallographica Section E: Structure Reports Online

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SN - 1600-5368

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