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

Suchada Chantrapromma, Patcharawadee Prachumrat, Pumsak Ruanwas, Nawong Boonnak, Mohammad Kassim

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The title compound, C15H14N2O3, crystallizes with two independent molecules (A and B) in the asymmetric unit that differ in the orientation of the 3-methoxyphenyl group with respect to the methylidenebenzohydrazide unit. The dihedral angles between the two benzene rings are 24.02-(10) and 29.30-(9)° in molecules A and B, respectively. In molecule A, the methoxy group is twisted slightly relative to its bound benzene ring, with a Cmethyl - O - C - C torsion angle of 14.2-(3)°, whereas it is almost co-planar in molecule B, where the corresponding angle is -2.4-(3)°. In the crystal, the molecules are linked by N - H⋯O, O - H⋯N and O - H⋯O hydrogen bonds, as well as by weak C - H⋯O interactions, forming sheets parallel to the bc plane. The N - H⋯O hydrogen bond and weak C - H⋯O interaction link different molecules (A⋯B) whereas both O - H⋯N and O - H⋯O hydrogen bonds link like molecules (A⋯A) and (B⋯B). Pairs of inversion-related B molecules are stacked approximately along the a axis by π-π interactions in which the distance between the centroids of the 3-methoxyphenyl rings is 3.5388-(12)-Å. The B molecules also participate in weak C - H⋯π interactions between the 4-hydroxyphenyl and the 3-methoxyphenyl rings.

Original languageEnglish
Pages (from-to)1339-1342
Number of pages4
JournalActa Crystallographica Section E: Crystallographic Communications
Volume72
DOIs
Publication statusPublished - 2016

Fingerprint

Crystal structure
crystal structure
Molecules
molecules
Hydrogen bonds
rings
hydrogen bonds
Benzene
benzene
interactions
Dihedral angle
Torsional stress
centroids
torsion
dihedral angle
inversions
Crystals
crystals

Keywords

  • Benzohydrazides
  • crystal structure
  • X-ray
  • α-glucosidase inhibitory

ASJC Scopus subject areas

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

Cite this

Crystal structure of (E)-4-hydroxy-N′-(3-methoxybenzylidene)benzohydrazide. / Chantrapromma, Suchada; Prachumrat, Patcharawadee; Ruanwas, Pumsak; Boonnak, Nawong; Kassim, Mohammad.

In: Acta Crystallographica Section E: Crystallographic Communications, Vol. 72, 2016, p. 1339-1342.

Research output: Contribution to journalArticle

Chantrapromma, Suchada ; Prachumrat, Patcharawadee ; Ruanwas, Pumsak ; Boonnak, Nawong ; Kassim, Mohammad. / Crystal structure of (E)-4-hydroxy-N′-(3-methoxybenzylidene)benzohydrazide. In: Acta Crystallographica Section E: Crystallographic Communications. 2016 ; Vol. 72. pp. 1339-1342.
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abstract = "The title compound, C15H14N2O3, crystallizes with two independent molecules (A and B) in the asymmetric unit that differ in the orientation of the 3-methoxyphenyl group with respect to the methylidenebenzohydrazide unit. The dihedral angles between the two benzene rings are 24.02-(10) and 29.30-(9)° in molecules A and B, respectively. In molecule A, the methoxy group is twisted slightly relative to its bound benzene ring, with a Cmethyl - O - C - C torsion angle of 14.2-(3)°, whereas it is almost co-planar in molecule B, where the corresponding angle is -2.4-(3)°. In the crystal, the molecules are linked by N - H⋯O, O - H⋯N and O - H⋯O hydrogen bonds, as well as by weak C - H⋯O interactions, forming sheets parallel to the bc plane. The N - H⋯O hydrogen bond and weak C - H⋯O interaction link different molecules (A⋯B) whereas both O - H⋯N and O - H⋯O hydrogen bonds link like molecules (A⋯A) and (B⋯B). Pairs of inversion-related B molecules are stacked approximately along the a axis by π-π interactions in which the distance between the centroids of the 3-methoxyphenyl rings is 3.5388-(12)-{\AA}. The B molecules also participate in weak C - H⋯π interactions between the 4-hydroxyphenyl and the 3-methoxyphenyl rings.",
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T1 - Crystal structure of (E)-4-hydroxy-N′-(3-methoxybenzylidene)benzohydrazide

AU - Chantrapromma, Suchada

AU - Prachumrat, Patcharawadee

AU - Ruanwas, Pumsak

AU - Boonnak, Nawong

AU - Kassim, Mohammad

PY - 2016

Y1 - 2016

N2 - The title compound, C15H14N2O3, crystallizes with two independent molecules (A and B) in the asymmetric unit that differ in the orientation of the 3-methoxyphenyl group with respect to the methylidenebenzohydrazide unit. The dihedral angles between the two benzene rings are 24.02-(10) and 29.30-(9)° in molecules A and B, respectively. In molecule A, the methoxy group is twisted slightly relative to its bound benzene ring, with a Cmethyl - O - C - C torsion angle of 14.2-(3)°, whereas it is almost co-planar in molecule B, where the corresponding angle is -2.4-(3)°. In the crystal, the molecules are linked by N - H⋯O, O - H⋯N and O - H⋯O hydrogen bonds, as well as by weak C - H⋯O interactions, forming sheets parallel to the bc plane. The N - H⋯O hydrogen bond and weak C - H⋯O interaction link different molecules (A⋯B) whereas both O - H⋯N and O - H⋯O hydrogen bonds link like molecules (A⋯A) and (B⋯B). Pairs of inversion-related B molecules are stacked approximately along the a axis by π-π interactions in which the distance between the centroids of the 3-methoxyphenyl rings is 3.5388-(12)-Å. The B molecules also participate in weak C - H⋯π interactions between the 4-hydroxyphenyl and the 3-methoxyphenyl rings.

AB - The title compound, C15H14N2O3, crystallizes with two independent molecules (A and B) in the asymmetric unit that differ in the orientation of the 3-methoxyphenyl group with respect to the methylidenebenzohydrazide unit. The dihedral angles between the two benzene rings are 24.02-(10) and 29.30-(9)° in molecules A and B, respectively. In molecule A, the methoxy group is twisted slightly relative to its bound benzene ring, with a Cmethyl - O - C - C torsion angle of 14.2-(3)°, whereas it is almost co-planar in molecule B, where the corresponding angle is -2.4-(3)°. In the crystal, the molecules are linked by N - H⋯O, O - H⋯N and O - H⋯O hydrogen bonds, as well as by weak C - H⋯O interactions, forming sheets parallel to the bc plane. The N - H⋯O hydrogen bond and weak C - H⋯O interaction link different molecules (A⋯B) whereas both O - H⋯N and O - H⋯O hydrogen bonds link like molecules (A⋯A) and (B⋯B). Pairs of inversion-related B molecules are stacked approximately along the a axis by π-π interactions in which the distance between the centroids of the 3-methoxyphenyl rings is 3.5388-(12)-Å. The B molecules also participate in weak C - H⋯π interactions between the 4-hydroxyphenyl and the 3-methoxyphenyl rings.

KW - Benzohydrazides

KW - crystal structure

KW - X-ray

KW - α-glucosidase inhibitory

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