Crystal structures and Hirshfeld surface analyses of seven 7-aryl-4,7-dioxoheptanoic acids

differing carboxylic acid interactions leading to dimers, chains and three-dimensional arrays

Ligia R. Gomes, John N. Low* (Corresponding Author), Alan B. Turner, Graeme J. R. Watson, Thomas C. Baddeley, James L. Wardell

*Corresponding author for this work

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Crystal structures and Hirshfeld surface analysis are reported of seven aryl-CO-CH2CH2COCH2CH2CO2H derivatives, namely aryl = 4-ClC6H4 , 1: 2-HOC6H4, 2: (2,4-(MeO)(2)C6H3, 3: 3,5-Me 2 -4-MeOC6H2, 4: 4-MeC6H4, 5: C6H5 , 6: 2,4-(HO)(2)C6H3, 7. There are significant differences in their molecular conformations and their crystal packing. Within the group of compounds, three different types of carboxylic acid intermolecular interactions are exhibited, all involving O-H center dot center dot center dot O hydrogen bonds. These three types are (i) symmetric R-2(2)(8) dimers formed from pairs of O-H center dot center dot center dot O hydrogen bonds in compounds 1-5, (ii) infinite 1D homo-assemblies of carboxylic groups (homoAA,A catemers), and (iii), a 3-D array, in which there are no direct carboxylic acid-carboxylic acid interactions, generated from O-H center dot center dot center dot O interactions of each carboxylic acid group with the hydroxyl and carbonyl groups of other molecules in 7. Each of the carboxylic acid groups in the catemer exhibit anti arrangements with all the carboxylic acid oxygen atoms lying in a plane. Disorder is exhibited in the carboxylic acid groups in 2 and 6. With the variety of oxygen substituents present in 1-7, a large number of O-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds are exhibited, resulting in all cases in three dimension assemblies. In 1 5, interlayer contacts between the carboxylic acid R-2(2)(8) dimers in rows, with differing sets of weaker C-H center dot center dot center dot O and/or C-H center dot center dot center dot pi interactions, result in the formation of two-molecular wide columns and/ or infinite sheets. While column and sheet sub structures can also be designated in compound 6, on linking the carboxylic acid groups with other substituents via C-H center dot center dot center dot O, C-H center dot center dot center dot pi and C-H center dot center dot center dot pi interactions, these differ from those in 1-5 due to the different arrangements of the CO2H groups.

Original languageEnglish
Pages (from-to)761-780
Number of pages20
JournalZeitschrift fur kristallographie-Crystalline materials
Volume233
Issue number11
Early online date3 May 2018
DOIs
Publication statusPublished - Nov 2018

Keywords

  • 7-aryl-4,7-dioxoheptanoic acids
  • carboxylic acid interactions
  • Hirshfeld surface calculations
  • intermolecular interactions
  • X-ray crystallography
  • DNA METHYLTRANSFERASE
  • crystallography
  • inhibitors

Cite this

Crystal structures and Hirshfeld surface analyses of seven 7-aryl-4,7-dioxoheptanoic acids : differing carboxylic acid interactions leading to dimers, chains and three-dimensional arrays. / Gomes, Ligia R.; Low, John N. (Corresponding Author); Turner, Alan B.; Watson, Graeme J. R.; Baddeley, Thomas C.; Wardell, James L.

In: Zeitschrift fur kristallographie-Crystalline materials, Vol. 233, No. 11, 11.2018, p. 761-780.

Research output: Contribution to journalArticle

@article{0da2d7e42d9548a7ac195aa774028ee9,
title = "Crystal structures and Hirshfeld surface analyses of seven 7-aryl-4,7-dioxoheptanoic acids: differing carboxylic acid interactions leading to dimers, chains and three-dimensional arrays",
abstract = "Crystal structures and Hirshfeld surface analysis are reported of seven aryl-CO-CH2CH2COCH2CH2CO2H derivatives, namely aryl = 4-ClC6H4 , 1: 2-HOC6H4, 2: (2,4-(MeO)(2)C6H3, 3: 3,5-Me 2 -4-MeOC6H2, 4: 4-MeC6H4, 5: C6H5 , 6: 2,4-(HO)(2)C6H3, 7. There are significant differences in their molecular conformations and their crystal packing. Within the group of compounds, three different types of carboxylic acid intermolecular interactions are exhibited, all involving O-H center dot center dot center dot O hydrogen bonds. These three types are (i) symmetric R-2(2)(8) dimers formed from pairs of O-H center dot center dot center dot O hydrogen bonds in compounds 1-5, (ii) infinite 1D homo-assemblies of carboxylic groups (homoAA,A catemers), and (iii), a 3-D array, in which there are no direct carboxylic acid-carboxylic acid interactions, generated from O-H center dot center dot center dot O interactions of each carboxylic acid group with the hydroxyl and carbonyl groups of other molecules in 7. Each of the carboxylic acid groups in the catemer exhibit anti arrangements with all the carboxylic acid oxygen atoms lying in a plane. Disorder is exhibited in the carboxylic acid groups in 2 and 6. With the variety of oxygen substituents present in 1-7, a large number of O-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds are exhibited, resulting in all cases in three dimension assemblies. In 1 5, interlayer contacts between the carboxylic acid R-2(2)(8) dimers in rows, with differing sets of weaker C-H center dot center dot center dot O and/or C-H center dot center dot center dot pi interactions, result in the formation of two-molecular wide columns and/ or infinite sheets. While column and sheet sub structures can also be designated in compound 6, on linking the carboxylic acid groups with other substituents via C-H center dot center dot center dot O, C-H center dot center dot center dot pi and C-H center dot center dot center dot pi interactions, these differ from those in 1-5 due to the different arrangements of the CO2H groups.",
keywords = "7-aryl-4,7-dioxoheptanoic acids, carboxylic acid interactions, Hirshfeld surface calculations, intermolecular interactions, X-ray crystallography, DNA METHYLTRANSFERASE, crystallography, inhibitors",
author = "Gomes, {Ligia R.} and Low, {John N.} and Turner, {Alan B.} and Watson, {Graeme J. R.} and Baddeley, {Thomas C.} and Wardell, {James L.}",
year = "2018",
month = "11",
doi = "10.1515/zkri-2017-2144",
language = "English",
volume = "233",
pages = "761--780",
journal = "Zeitschrift fur kristallographie-Crystalline materials",
issn = "2194-4946",
publisher = "Walter de Gruyter GmbH",
number = "11",

}

TY - JOUR

T1 - Crystal structures and Hirshfeld surface analyses of seven 7-aryl-4,7-dioxoheptanoic acids

T2 - differing carboxylic acid interactions leading to dimers, chains and three-dimensional arrays

AU - Gomes, Ligia R.

AU - Low, John N.

AU - Turner, Alan B.

AU - Watson, Graeme J. R.

AU - Baddeley, Thomas C.

AU - Wardell, James L.

PY - 2018/11

Y1 - 2018/11

N2 - Crystal structures and Hirshfeld surface analysis are reported of seven aryl-CO-CH2CH2COCH2CH2CO2H derivatives, namely aryl = 4-ClC6H4 , 1: 2-HOC6H4, 2: (2,4-(MeO)(2)C6H3, 3: 3,5-Me 2 -4-MeOC6H2, 4: 4-MeC6H4, 5: C6H5 , 6: 2,4-(HO)(2)C6H3, 7. There are significant differences in their molecular conformations and their crystal packing. Within the group of compounds, three different types of carboxylic acid intermolecular interactions are exhibited, all involving O-H center dot center dot center dot O hydrogen bonds. These three types are (i) symmetric R-2(2)(8) dimers formed from pairs of O-H center dot center dot center dot O hydrogen bonds in compounds 1-5, (ii) infinite 1D homo-assemblies of carboxylic groups (homoAA,A catemers), and (iii), a 3-D array, in which there are no direct carboxylic acid-carboxylic acid interactions, generated from O-H center dot center dot center dot O interactions of each carboxylic acid group with the hydroxyl and carbonyl groups of other molecules in 7. Each of the carboxylic acid groups in the catemer exhibit anti arrangements with all the carboxylic acid oxygen atoms lying in a plane. Disorder is exhibited in the carboxylic acid groups in 2 and 6. With the variety of oxygen substituents present in 1-7, a large number of O-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds are exhibited, resulting in all cases in three dimension assemblies. In 1 5, interlayer contacts between the carboxylic acid R-2(2)(8) dimers in rows, with differing sets of weaker C-H center dot center dot center dot O and/or C-H center dot center dot center dot pi interactions, result in the formation of two-molecular wide columns and/ or infinite sheets. While column and sheet sub structures can also be designated in compound 6, on linking the carboxylic acid groups with other substituents via C-H center dot center dot center dot O, C-H center dot center dot center dot pi and C-H center dot center dot center dot pi interactions, these differ from those in 1-5 due to the different arrangements of the CO2H groups.

AB - Crystal structures and Hirshfeld surface analysis are reported of seven aryl-CO-CH2CH2COCH2CH2CO2H derivatives, namely aryl = 4-ClC6H4 , 1: 2-HOC6H4, 2: (2,4-(MeO)(2)C6H3, 3: 3,5-Me 2 -4-MeOC6H2, 4: 4-MeC6H4, 5: C6H5 , 6: 2,4-(HO)(2)C6H3, 7. There are significant differences in their molecular conformations and their crystal packing. Within the group of compounds, three different types of carboxylic acid intermolecular interactions are exhibited, all involving O-H center dot center dot center dot O hydrogen bonds. These three types are (i) symmetric R-2(2)(8) dimers formed from pairs of O-H center dot center dot center dot O hydrogen bonds in compounds 1-5, (ii) infinite 1D homo-assemblies of carboxylic groups (homoAA,A catemers), and (iii), a 3-D array, in which there are no direct carboxylic acid-carboxylic acid interactions, generated from O-H center dot center dot center dot O interactions of each carboxylic acid group with the hydroxyl and carbonyl groups of other molecules in 7. Each of the carboxylic acid groups in the catemer exhibit anti arrangements with all the carboxylic acid oxygen atoms lying in a plane. Disorder is exhibited in the carboxylic acid groups in 2 and 6. With the variety of oxygen substituents present in 1-7, a large number of O-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds are exhibited, resulting in all cases in three dimension assemblies. In 1 5, interlayer contacts between the carboxylic acid R-2(2)(8) dimers in rows, with differing sets of weaker C-H center dot center dot center dot O and/or C-H center dot center dot center dot pi interactions, result in the formation of two-molecular wide columns and/ or infinite sheets. While column and sheet sub structures can also be designated in compound 6, on linking the carboxylic acid groups with other substituents via C-H center dot center dot center dot O, C-H center dot center dot center dot pi and C-H center dot center dot center dot pi interactions, these differ from those in 1-5 due to the different arrangements of the CO2H groups.

KW - 7-aryl-4,7-dioxoheptanoic acids

KW - carboxylic acid interactions

KW - Hirshfeld surface calculations

KW - intermolecular interactions

KW - X-ray crystallography

KW - DNA METHYLTRANSFERASE

KW - crystallography

KW - inhibitors

U2 - 10.1515/zkri-2017-2144

DO - 10.1515/zkri-2017-2144

M3 - Article

VL - 233

SP - 761

EP - 780

JO - Zeitschrift fur kristallographie-Crystalline materials

JF - Zeitschrift fur kristallographie-Crystalline materials

SN - 2194-4946

IS - 11

ER -