Supramolecular structures of five 5-(arylmethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones: isolated molecules, hydrogen-bonded chains and chains of fused hydrogen-bonded rings

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

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Abstract

In each of the five title compounds, namely 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C13H12N2O3, (I), 5-(3-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,-3H,-5H)-trione, C14H14N2O4, (II), 5-(4-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C14H14N2O4, (III), 5-[4-(dimethylamino)benzylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C15H17N3O3, (IV), and 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C21H28N2O4, (V), which crystallizes with Z' = 2 in PT, there is a very wide C-C-C angle at the methine C atom linking the two rings, ranging from 137.1 (2)° in (I) to 139.14 (14)° in (III). There is evidence for intramolecular charge separation in (IV) and, to a lesser degree, in (III). The molecules of (I)-(III) are linked by pairs of C-H••• O hydrogen bonds into chains of edge-fused rings, with alternating R-2(2)(14) and R-2(2)(16) rings in (I), alternating R-2(2)(14) and R-4(4)(20) rings in (II), with two types of R-2(2)(16) rings alternating in (111). The molecules in (IV) are linked by a single C-H••• O hydrogen bond into simple C(8) chains, but there are no direction-specific intermolecular interactions in M.

Original languageEnglish
Pages (from-to)o306-o311
Number of pages6
JournalActa Crystallographica Section C, Crystal Structure Communications
Volume61
Issue number5
DOIs
Publication statusPublished - May 2005

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Hydrogen
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Keywords

  • merocyanine-type dyes
  • baribituric-acid
  • X-Ray
  • diffraction

Cite this

@article{ff953e4ea6064d7a9d43c4f225443219,
title = "Supramolecular structures of five 5-(arylmethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones: isolated molecules, hydrogen-bonded chains and chains of fused hydrogen-bonded rings",
abstract = "In each of the five title compounds, namely 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C13H12N2O3, (I), 5-(3-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,-3H,-5H)-trione, C14H14N2O4, (II), 5-(4-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C14H14N2O4, (III), 5-[4-(dimethylamino)benzylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C15H17N3O3, (IV), and 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C21H28N2O4, (V), which crystallizes with Z' = 2 in PT, there is a very wide C-C-C angle at the methine C atom linking the two rings, ranging from 137.1 (2)° in (I) to 139.14 (14)° in (III). There is evidence for intramolecular charge separation in (IV) and, to a lesser degree, in (III). The molecules of (I)-(III) are linked by pairs of C-H••• O hydrogen bonds into chains of edge-fused rings, with alternating R-2(2)(14) and R-2(2)(16) rings in (I), alternating R-2(2)(14) and R-4(4)(20) rings in (II), with two types of R-2(2)(16) rings alternating in (111). The molecules in (IV) are linked by a single C-H••• O hydrogen bond into simple C(8) chains, but there are no direction-specific intermolecular interactions in M.",
keywords = "merocyanine-type dyes, baribituric-acid, X-Ray, diffraction",
author = "Rezende, {M C} and M Dominguez and Wardell, {J L} and Skakle, {J M S} and Low, {J N} and C Glidewell",
year = "2005",
month = "5",
doi = "10.1107/S0108270105008498",
language = "English",
volume = "61",
pages = "o306--o311",
journal = "Acta Crystallographica Section C, Crystal Structure Communications",
issn = "0108-2701",
publisher = "Wiley-Blackwell",
number = "5",

}

TY - JOUR

T1 - Supramolecular structures of five 5-(arylmethylene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-triones: isolated molecules, hydrogen-bonded chains and chains of fused hydrogen-bonded rings

AU - Rezende, M C

AU - Dominguez, M

AU - Wardell, J L

AU - Skakle, J M S

AU - Low, J N

AU - Glidewell, C

PY - 2005/5

Y1 - 2005/5

N2 - In each of the five title compounds, namely 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C13H12N2O3, (I), 5-(3-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,-3H,-5H)-trione, C14H14N2O4, (II), 5-(4-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C14H14N2O4, (III), 5-[4-(dimethylamino)benzylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C15H17N3O3, (IV), and 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C21H28N2O4, (V), which crystallizes with Z' = 2 in PT, there is a very wide C-C-C angle at the methine C atom linking the two rings, ranging from 137.1 (2)° in (I) to 139.14 (14)° in (III). There is evidence for intramolecular charge separation in (IV) and, to a lesser degree, in (III). The molecules of (I)-(III) are linked by pairs of C-H••• O hydrogen bonds into chains of edge-fused rings, with alternating R-2(2)(14) and R-2(2)(16) rings in (I), alternating R-2(2)(14) and R-4(4)(20) rings in (II), with two types of R-2(2)(16) rings alternating in (111). The molecules in (IV) are linked by a single C-H••• O hydrogen bond into simple C(8) chains, but there are no direction-specific intermolecular interactions in M.

AB - In each of the five title compounds, namely 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C13H12N2O3, (I), 5-(3-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,-3H,-5H)-trione, C14H14N2O4, (II), 5-(4-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C14H14N2O4, (III), 5-[4-(dimethylamino)benzylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C15H17N3O3, (IV), and 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C21H28N2O4, (V), which crystallizes with Z' = 2 in PT, there is a very wide C-C-C angle at the methine C atom linking the two rings, ranging from 137.1 (2)° in (I) to 139.14 (14)° in (III). There is evidence for intramolecular charge separation in (IV) and, to a lesser degree, in (III). The molecules of (I)-(III) are linked by pairs of C-H••• O hydrogen bonds into chains of edge-fused rings, with alternating R-2(2)(14) and R-2(2)(16) rings in (I), alternating R-2(2)(14) and R-4(4)(20) rings in (II), with two types of R-2(2)(16) rings alternating in (111). The molecules in (IV) are linked by a single C-H••• O hydrogen bond into simple C(8) chains, but there are no direction-specific intermolecular interactions in M.

KW - merocyanine-type dyes

KW - baribituric-acid

KW - X-Ray

KW - diffraction

U2 - 10.1107/S0108270105008498

DO - 10.1107/S0108270105008498

M3 - Article

VL - 61

SP - o306-o311

JO - Acta Crystallographica Section C, Crystal Structure Communications

JF - Acta Crystallographica Section C, Crystal Structure Communications

SN - 0108-2701

IS - 5

ER -