Crystal structure of (E)-2-cyano-3-(12-methyl-12H-benzo[b]phenothiazin-11-yl)acrylic acid

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Abstract

In the title compound, C21H14N2O2S, a donor-acceptor type of benzo[b]phenothiazine (bpz) derivative, the thiazine ring adopts a boat conformation and the bond-angle sum at the N atom is 360.0°. The dihedral angle between the benzene ring and the naphthelene ring system fused to the thiazine ring is 32.76(5)°. In the crystal, carboxylic-acid inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 2(8) loops. Aromatic π-π stacking [shortest centroid-centroid separaton = 3.5242(13)Å] consolidates the structure and very weak C-H⋯O and C-H⋯N interactions also occur.

Original languageEnglish
Pages (from-to)o1026-o1027
JournalActa Crystallographica Section E: Structure Reports Online
Volume70
Issue number9
DOIs
Publication statusPublished - Aug 6 2014

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Thiazines
Boats
acrylic acid
Dihedral angle
Carboxylic acids
Dimers
Acrylics
Conformations
Benzene
Hydrogen bonds
Crystal structure
thiazine (trademark)
Derivatives
Atoms
Crystals
crystal structure
Acids
rings
Carboxylic Acids
centroids

All Science Journal Classification (ASJC) codes

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

Cite this

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title = "Crystal structure of (E)-2-cyano-3-(12-methyl-12H-benzo[b]phenothiazin-11-yl)acrylic acid",
abstract = "In the title compound, C21H14N2O2S, a donor-acceptor type of benzo[b]phenothiazine (bpz) derivative, the thiazine ring adopts a boat conformation and the bond-angle sum at the N atom is 360.0°. The dihedral angle between the benzene ring and the naphthelene ring system fused to the thiazine ring is 32.76(5)°. In the crystal, carboxylic-acid inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 2(8) loops. Aromatic π-π stacking [shortest centroid-centroid separaton = 3.5242(13){\AA}] consolidates the structure and very weak C-H⋯O and C-H⋯N interactions also occur.",
author = "Motonori Watanabe and Tatsumi Ishihara",
year = "2014",
month = "8",
day = "6",
doi = "10.1107/S1600536814018388",
language = "English",
volume = "70",
pages = "o1026--o1027",
journal = "Acta Crystallographica Section E: Structure Reports Online",
issn = "1600-5368",
publisher = "International Union of Crystallography",
number = "9",

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TY - JOUR

T1 - Crystal structure of (E)-2-cyano-3-(12-methyl-12H-benzo[b]phenothiazin-11-yl)acrylic acid

AU - Watanabe, Motonori

AU - Ishihara, Tatsumi

PY - 2014/8/6

Y1 - 2014/8/6

N2 - In the title compound, C21H14N2O2S, a donor-acceptor type of benzo[b]phenothiazine (bpz) derivative, the thiazine ring adopts a boat conformation and the bond-angle sum at the N atom is 360.0°. The dihedral angle between the benzene ring and the naphthelene ring system fused to the thiazine ring is 32.76(5)°. In the crystal, carboxylic-acid inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 2(8) loops. Aromatic π-π stacking [shortest centroid-centroid separaton = 3.5242(13)Å] consolidates the structure and very weak C-H⋯O and C-H⋯N interactions also occur.

AB - In the title compound, C21H14N2O2S, a donor-acceptor type of benzo[b]phenothiazine (bpz) derivative, the thiazine ring adopts a boat conformation and the bond-angle sum at the N atom is 360.0°. The dihedral angle between the benzene ring and the naphthelene ring system fused to the thiazine ring is 32.76(5)°. In the crystal, carboxylic-acid inversion dimers linked by pairs of O-H⋯O hydrogen bonds generate R 2 2(8) loops. Aromatic π-π stacking [shortest centroid-centroid separaton = 3.5242(13)Å] consolidates the structure and very weak C-H⋯O and C-H⋯N interactions also occur.

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JF - Acta Crystallographica Section E: Structure Reports Online

SN - 1600-5368

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ER -