Crystal structure of (<i>E</i>)-4-hydroxy-<i>N</i>′-(3-methoxybenzylidene)benzohydrazide

In the title benzohydrazide derivative, C14H12N2O4, the azomethine C=N double bond has an E configuration. The hydrazide connecting bridge, (C=O)—(NH)—N=(CH), is nearly planar with C—C—N—N and C—N—N=C torsion angles of −177.33 (10) and −174.98 (12)°, respectively. The 4-hydroxyphenyl and 3,4-dihydroxyphenyl rings are slightly twisted, making a dihedral angle of 9.18 (6)°. In the crystal, molecules are connected by N—H...O and O—H...O hydrogen bonds into a three-dimensional network, while further consolidated via π–π interactions [centroid–centroid distances = 3.6480 (8) and 3.7607 (8) Å]. The conformation is compared to those of related benzylidene-4-hydroxybenzohydrazide derivatives.

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Crystal structure of (E)-N′-(3,4-dihydroxybenzylidene)-4-hydroxybenzohydrazide

Chantrapromma

Kwong

Prachumrat

et al. 2019

Acta Cryst E

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Crystal structure of 4-[(4-methylbenzyl)oxy]-N′-(4-nitrobenzylidene)benzohydrazide: a new hydrazone derivative

Banna¹,

Sheikh²,

Miyatake³

et al. 2023

Acta Cryst E

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Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl)propylidene)-4-hydroxybenzohydrazide, C₁₆H₁₅ClN₂O₃

2022

Zeitschrift Für Kristallographie - New Crystal Structures

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Crystal structure of (E)-4-hydroxy-N′-(3-methoxybenzylidene)benzohydrazide

Abstract: The molecules of C15H14N2O3 are slightly twisted. N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds play an important role in the crystal packing, resulting in the formation of molecular sheets parallel to the bc plane.

Cited by 3 publications

References 16 publications

Crystal structure of (E)-N′-(3,4-dihydroxybenzylidene)-4-hydroxybenzohydrazide

Crystal structure of (E)-N′-(3,4-dihydroxybenzylidene)-4-hydroxybenzohydrazide

Crystal structure of 4-[(4-methylbenzyl)oxy]-N′-(4-nitrobenzylidene)benzohydrazide: a new hydrazone derivative

Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl)propylidene)-4-hydroxybenzohydrazide, C₁₆H₁₅ClN₂O₃

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Crystal structure of (E)-4-hydroxy-N′-(3-methoxybenzylidene)benzohydrazide

Abstract: The mol­ecules of C15H14N2O3 are slightly twisted. N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds play an important role in the crystal packing, resulting in the formation of mol­ecular sheets parallel to the bc plane.

Cited by 3 publications

References 16 publications

Crystal structure of (E)-N′-(3,4-dihydroxybenzylidene)-4-hydroxybenzohydrazide

Crystal structure of (E)-N′-(3,4-dihydroxybenzylidene)-4-hydroxybenzohydrazide

Crystal structure of 4-[(4-methylbenzyl)oxy]-N′-(4-nitrobenzylidene)benzohydrazide: a new hydrazone derivative

Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl)propylidene)-4-hydroxybenzohydrazide, C16H15ClN2O3

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Abstract: The molecules of C15H14N2O3 are slightly twisted. N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds play an important role in the crystal packing, resulting in the formation of molecular sheets parallel to the bc plane.

Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl)propylidene)-4-hydroxybenzohydrazide, C₁₆H₁₅ClN₂O₃