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Crystal structure of 10‐(2′‐pyrazyl)phenothiazine and spectroscopic identification of its radical‐cations and dications
Author(s) -
Jovanovic Misa V.,
Biehl Edward R.,
Rosenstein Robert D.,
Chu Shirley S. C.
Publication year - 1984
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570210307
Subject(s) - phenothiazine , chemistry , orthorhombic crystal system , crystallography , dihedral angle , ring (chemistry) , substituent , crystal structure , crystal (programming language) , oxidizing agent , molecule , stereochemistry , hydrogen bond , organic chemistry , medicine , computer science , programming language , pharmacology
The crystal structure of 10‐(2′‐pyrazyl)phenothiazine has been determined by the single crystal x‐ray diffraction technique. The crystal belongs to the orthorhombic system with a space group of Pbca. The unit cell parameters are a = 10.633(3), b = 7.525(2), and c = 32.984(6)Å, with eight molecules in a unit cell. The final disagreement index, R, is 0.057 for 1944 observed reflections. The central ring of the phenothiazine ring system is in a broad conformation and the 10‐(2′‐pyrazyl)substituent is attached to the phenothiazine central ring in a boat‐axial conformation. This is the first reported phenothiazine whose 10‐substituent is perpendicular to the plane bisecting the dihedral angle of the phenothiazine nucleus. Ultraviolet absorption maxima of the title compound in various oxidizing and non‐oxidizing medium is reported. These data indicate that the geometry of 3 changes when it is oxidized to its radical‐cations and dications.