Concomitant polymorphism and a temperature-dependent phase change in (E)-[1-( 4-methoxy-phenyl)3-phenyl-2-propenylideneamino] oxyacetic acid

J M S Skakle, J N Low, J L Wardell, C Glidewell

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7 Citations (Scopus)

Abstract

The title compound, C18H17NO4, crystallizes from ethanol at ambient temperature as two concomitant polymorphs (I) and (II), both monoclinic P2(1)/c with Z' = 1. The less abundant form (I) undergoes a reversible phase-transition at ca 173 K to a third monoclinic polymorph (III), P2(1)/n, with Z' = 2, while the more abundant polymorph (II) is unchanged down to 120 K. In each polymorph of (I)-(III) the molecules are linked by pairs of O-H••• O hydrogen bonds into cyclic dimers which are crystallographically centrosymmetric in (I) and (II), and approximately, but not crystallographically, centrosymmetric in (III). There are no direction-specific interactions between the hydrogen-bonded dimers in polymorph (I); in polymorph (II) the dimers are linked into sheets by C-H••• N and C-H•••π(arene) hydrogen bonds; in polymorph (III) the dimers are linked into chains by a C-H•••π(arene) hydrogen bond. The interconversion of polymorphs (I) and (III) is a simple displacive phase transition.

Original languageEnglish
Pages (from-to)321-328
Number of pages8
JournalActa Crystallographica Section B, Structural Science
VolumeB61
DOIs
Publication statusPublished - 2005

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Polymorphism
Hydrogen
Temperature
Acids
Phase Transition
Dimers
Hydrogen bonds
Ethanol
Phase transitions
Molecules

Keywords

  • Pi-stacking interactions
  • Bonded r-2(2)(8) dimers
  • Hydrogen-bonds
  • X-ray
  • Diffraction
  • Benzanilide
  • Interplay
  • Crystals

Cite this

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title = "Concomitant polymorphism and a temperature-dependent phase change in (E)-[1-( 4-methoxy-phenyl)3-phenyl-2-propenylideneamino] oxyacetic acid",
abstract = "The title compound, C18H17NO4, crystallizes from ethanol at ambient temperature as two concomitant polymorphs (I) and (II), both monoclinic P2(1)/c with Z' = 1. The less abundant form (I) undergoes a reversible phase-transition at ca 173 K to a third monoclinic polymorph (III), P2(1)/n, with Z' = 2, while the more abundant polymorph (II) is unchanged down to 120 K. In each polymorph of (I)-(III) the molecules are linked by pairs of O-H••• O hydrogen bonds into cyclic dimers which are crystallographically centrosymmetric in (I) and (II), and approximately, but not crystallographically, centrosymmetric in (III). There are no direction-specific interactions between the hydrogen-bonded dimers in polymorph (I); in polymorph (II) the dimers are linked into sheets by C-H••• N and C-H•••π(arene) hydrogen bonds; in polymorph (III) the dimers are linked into chains by a C-H•••π(arene) hydrogen bond. The interconversion of polymorphs (I) and (III) is a simple displacive phase transition.",
keywords = "Pi-stacking interactions, Bonded r-2(2)(8) dimers, Hydrogen-bonds, X-ray, Diffraction, Benzanilide, Interplay, Crystals",
author = "Skakle, {J M S} and Low, {J N} and Wardell, {J L} and C Glidewell",
year = "2005",
doi = "10.1107/S0108768105007421",
language = "English",
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pages = "321--328",
journal = "Acta Crystallographica Section B, Structural Science",
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publisher = "International Union of Crystallography",

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TY - JOUR

T1 - Concomitant polymorphism and a temperature-dependent phase change in (E)-[1-( 4-methoxy-phenyl)3-phenyl-2-propenylideneamino] oxyacetic acid

AU - Skakle, J M S

AU - Low, J N

AU - Wardell, J L

AU - Glidewell, C

PY - 2005

Y1 - 2005

N2 - The title compound, C18H17NO4, crystallizes from ethanol at ambient temperature as two concomitant polymorphs (I) and (II), both monoclinic P2(1)/c with Z' = 1. The less abundant form (I) undergoes a reversible phase-transition at ca 173 K to a third monoclinic polymorph (III), P2(1)/n, with Z' = 2, while the more abundant polymorph (II) is unchanged down to 120 K. In each polymorph of (I)-(III) the molecules are linked by pairs of O-H••• O hydrogen bonds into cyclic dimers which are crystallographically centrosymmetric in (I) and (II), and approximately, but not crystallographically, centrosymmetric in (III). There are no direction-specific interactions between the hydrogen-bonded dimers in polymorph (I); in polymorph (II) the dimers are linked into sheets by C-H••• N and C-H•••π(arene) hydrogen bonds; in polymorph (III) the dimers are linked into chains by a C-H•••π(arene) hydrogen bond. The interconversion of polymorphs (I) and (III) is a simple displacive phase transition.

AB - The title compound, C18H17NO4, crystallizes from ethanol at ambient temperature as two concomitant polymorphs (I) and (II), both monoclinic P2(1)/c with Z' = 1. The less abundant form (I) undergoes a reversible phase-transition at ca 173 K to a third monoclinic polymorph (III), P2(1)/n, with Z' = 2, while the more abundant polymorph (II) is unchanged down to 120 K. In each polymorph of (I)-(III) the molecules are linked by pairs of O-H••• O hydrogen bonds into cyclic dimers which are crystallographically centrosymmetric in (I) and (II), and approximately, but not crystallographically, centrosymmetric in (III). There are no direction-specific interactions between the hydrogen-bonded dimers in polymorph (I); in polymorph (II) the dimers are linked into sheets by C-H••• N and C-H•••π(arene) hydrogen bonds; in polymorph (III) the dimers are linked into chains by a C-H•••π(arene) hydrogen bond. The interconversion of polymorphs (I) and (III) is a simple displacive phase transition.

KW - Pi-stacking interactions

KW - Bonded r-2(2)(8) dimers

KW - Hydrogen-bonds

KW - X-ray

KW - Diffraction

KW - Benzanilide

KW - Interplay

KW - Crystals

U2 - 10.1107/S0108768105007421

DO - 10.1107/S0108768105007421

M3 - Article

VL - B61

SP - 321

EP - 328

JO - Acta Crystallographica Section B, Structural Science

JF - Acta Crystallographica Section B, Structural Science

SN - 0108-7681

ER -