N′-(2,3-Dihydroxybenzylidene)isonicotinohydrazide

Abstract

The title compound, C13H11N3O3, crystallized with two independent mol­ecules in the asymmetric unit. One of the mol­ecules is twisted while the other is almost planar, with dihedral angles of 28.02 (6) and 2.42 (9)°, respectively, between the benzene and pyridine rings. Intra­molecular O—H⋯O and O—H⋯N hydrogen bonds are present in both mol­ecules. The two independent mol­ecules are linked by pairs of O—H⋯O hydrogen bonds. The crystal structure is further stabilized by inter­molecular N—H⋯N hydrogen bonds and C—H⋯N and C—H⋯O inter­actions.

(E)-N-(1-Benzothiophen-3-ylmethylidene)-2,6-dimethylaniline

“…The dihedral angle between the methylenemethanamine and bezothiophene group is 3.22 (50)°. The length of the C9=N1 double bond is 1.260 (3) Å, slightly shorter than standard 1.28 Å value of a C=N double bond and consistent with related structures (Ağar et al, 2010;Ceylan et al 2011;Dege, Şekerci et al, 2006;Genç et al 2004;İnaç et al, 2012;Tanak et al, 2010;Tecer et al, 2010).…”

“…For chemical properties of Schiff bases, see: Aydog an et al 2001; Tanak et al (2010); Ingold (1969). For related structures, see: Ag ar et al (2010); Ceylan et al (2011); Dege, Ş ekerci et al (2006); Demirtaş et al (2009); Dege, Içbudak & Adıyaman (2006; Genç et al (2004); İnaç et al (2012); Tecer et al (2010). For the structural properties benzothiophene derivatives, see: Alarcon et al (1999); Cohen et al (1964); Hadjoudis et al (1987); Inamoto et al (2008); Kö ysal et al (2007); Karabıyık et al (2008); Kobayashi et al (2009); Mlochowski & Potaczek (2009); Novopoltseva (1995); Tanak et al (2010); Xu et al (1994); Zhang et al (2001).…”

2-{(E)-[(3-Iodo-4-methylphenyl)imino]methyl}-4-(trifluoromethoxy)phenol

“…The C5-N1-C13-C7 torsion angle is 179.4 (3)°. The C13═N1 bond distance [1.272 (5) Å] is consistent with related structures (Aǧar et al, 2010;Tecer et al, 2010;Ceylan et al, 2011;Demirtaş et al, 2009).…”

“…Schiff base compounds can be classified by their photochromic and thermochromic characteristics, see: Alarcon et al (1999); Cohen et al (1964); Gü l et al (2007); Hadjoudis et al (1987); Ş ahin et al (2005); Xu et al (1994). For related structures, see: Ag ar et al 2010); Ceylan et al (2011); Demirtaş et al (2009); Tecer et al (2010). For hydrogen-bond motifs, see: Bernstein et al (1995).…”

Effective methods for the synthesis of hydrazones, quinazolines, and Schiff bases: reaction monitoring using a chemometric approach

“…It should be noted that in Cambridge Structural Database (CSD) 22 there are few hydrazone structures reported with 2,3-and 2,4-dihydroxybenzaldehyde fragment. [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40] All of the investigated compounds were further characterized by elemental analysis, thermogravimetric and differential scanning calorimetry measurements, IR-ATR and NMR spectroscopy. The solid-state thermochromic changes of azines and inuence of the central spacer and functional groups on the responsive properties were also explored.…”