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( E )-2-{(2-Hydroxynaphthalen-1-yl)methylene}hydrazinecarboxamide

Journal Article · · Acta Crystallographica. Section E
 [1];  [2];  [3];  [4]
  1. Morgan State Univ., Baltimore, MD (United States). Dept. of Chemistry; DOE/OSTI
  2. Morgan State Univ., Baltimore, MD (United States). Dept. of Chemistry
  3. Howard Univ., Washington, DC (United States). Dept. of Chemistry
  4. Keene State College, Keene, NH (United States). Dept. of Chemistry
+ Show Author Affiliations

In the title molecule, C12H11N3O2, the dihedral angle between the mean planes of the naphthalene and carboxamide groups is 28.9 (8)°. The hydrazine N atoms are twisted slightly out of the plane of the carboxamide group [C—C—N—N torsion angle = 175.06 (13)°]. The crystal packing is influenced by N—HO hydrogen bonding which includes a bifurcated hydrogen bond between the amide N atom and nearby carboxyl and hydroxyl O atoms. A second bifurcated hydrogen bond occurs between the hydroxyl O atom and nearby amide (intermolecular) and hydrazine (intramolecular) N atoms. As a result, molecules are linked into a co-operative hydrogen-bonded network of infinite one dimensional O—HO—HO—H chains along the (101) plane of the unit cell in a zigzag pattern, the dihedral angle between the mean planes of the naphthalene groups of adjacent molecules in the chain being 86.9 (2)°. A MOPAC PM3 calculation provides support to these observations.

Research Organization:
Morgan State Univ., Baltimore, MD (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division
Grant/Contract Number:
FG02-03ER63580
OSTI ID:
1625732
Journal Information:
Acta Crystallographica. Section E, Journal Name: Acta Crystallographica. Section E Journal Issue: 5 Vol. 65; ISSN ACSEBH; ISSN 1600-5368
Publisher:
International Union of CrystallographyCopyright Statement
Country of Publication:
United States
Language:
English

References (5)

Spectral characterization of a newly synthesized fluorescent semicarbazone derivative and its usage as a selective fiber optic sensor for copper(II) journal February 2007
Synthesis and characterization of some new Schiff base polymers journal April 2004
Vanadium(V) complexes with salicylaldehyde semicarbazone derivatives bearing in vitro anti-tumor activity toward kidney tumor cells (TK-10): crystal structure of [VVO2(5-bromosalicylaldehyde semicarbazone)] journal February 2005
A short history of SHELX journal December 2007
The Wide Pharmacological Versatility of Semicarbazones, Thiosemicarbazones and Their Metal Complexes journal January 2004

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Crystallography