Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid
The anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with 4-aminobenzoic acid [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 4-aminobenzoate, C9H17N2+·C7H6NO2− (I)], 3,5-dinitrobenzoic acid [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 3,5-dinitrobenzoate, C9H17N2+·C7H3N2O6−, (II)] an...
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doaj-391e015de65f4c1ba9a2d1a015966ca12020-11-25T00:22:41ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902016-03-0172338238610.1107/S205698901600267Xpk2574Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acidGraham Smith0Daniel E. Lynch1Science and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, AustraliaExilica Ltd, The Technocentre, Puma Way, Coventry CV1 2TT, EnglandThe anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with 4-aminobenzoic acid [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 4-aminobenzoate, C9H17N2+·C7H6NO2− (I)], 3,5-dinitrobenzoic acid [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 3,5-dinitrobenzoate, C9H17N2+·C7H3N2O6−, (II)] and 3,5-dinitrosalicylic acid (DNSA) [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 2-hydroxy-3,5-dinitrobenzoate, C9H17N2+·C7H3N2O7−, (III)] have been determined and their hydrogen-bonded structures are described. In both (II) and (III), the DBU cations have a common disorder in three of the C atoms of the six-membered ring moieties [site-occupancy factors (SOF) = 0.735 (3)/0.265 (3) and 0.686 (4)/0.314 (4), respectively], while in (III), there is additional rotational disorder in the DNSA anion, giving two sites (SOF = 0.72/0.28, values fixed) for the phenol group. In the crystals of (I) and (III), the cation–anion pairs are linked through a primary N—H...Ocarboxyl hydrogen bond [2.665 (2) and 2.869 (3) Å, respectively]. In (II), the ion pairs are linked through an asymmetric three-centre R12(4), N—H...O,O′ chelate association. In (I), structure extension is through amine N—H...Ocarboxyl hydrogen bonds between the PABA anions, giving a three-dimensional structure. The crystal structures of (II) and (III) are very similar, the cation–anion pairs being associated only through weak C—H...O hydrogen bonds, giving in both overall two-dimensional layered structures lying parallel to (001). No π–π ring associations are present in any of the structures.http://scripts.iucr.org/cgi-bin/paper?S205698901600267Xcrystal structure1,8-diazabicyclo[5.4.0]undec-7-eneBDUbenzoate saltshydrogen bonding |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Graham Smith Daniel E. Lynch |
spellingShingle |
Graham Smith Daniel E. Lynch Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid Acta Crystallographica Section E: Crystallographic Communications crystal structure 1,8-diazabicyclo[5.4.0]undec-7-ene BDU benzoate salts hydrogen bonding |
author_facet |
Graham Smith Daniel E. Lynch |
author_sort |
Graham Smith |
title |
Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid |
title_short |
Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid |
title_full |
Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid |
title_fullStr |
Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid |
title_full_unstemmed |
Crystal structures of three anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid |
title_sort |
crystal structures of three anhydrous salts of the lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (dbu) with the ring-substituted benzoic acid analogues 4-aminobenzoic acid, 3,5-dinitrobenzoic acid and 3,5-dinitrosalicylic acid |
publisher |
International Union of Crystallography |
series |
Acta Crystallographica Section E: Crystallographic Communications |
issn |
2056-9890 |
publishDate |
2016-03-01 |
description |
The anhydrous salts of the Lewis base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with 4-aminobenzoic acid [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 4-aminobenzoate, C9H17N2+·C7H6NO2− (I)], 3,5-dinitrobenzoic acid [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 3,5-dinitrobenzoate, C9H17N2+·C7H3N2O6−, (II)] and 3,5-dinitrosalicylic acid (DNSA) [1-aza-8-azoniabicyclo[5.4.0]undec-7-ene 2-hydroxy-3,5-dinitrobenzoate, C9H17N2+·C7H3N2O7−, (III)] have been determined and their hydrogen-bonded structures are described. In both (II) and (III), the DBU cations have a common disorder in three of the C atoms of the six-membered ring moieties [site-occupancy factors (SOF) = 0.735 (3)/0.265 (3) and 0.686 (4)/0.314 (4), respectively], while in (III), there is additional rotational disorder in the DNSA anion, giving two sites (SOF = 0.72/0.28, values fixed) for the phenol group. In the crystals of (I) and (III), the cation–anion pairs are linked through a primary N—H...Ocarboxyl hydrogen bond [2.665 (2) and 2.869 (3) Å, respectively]. In (II), the ion pairs are linked through an asymmetric three-centre R12(4), N—H...O,O′ chelate association. In (I), structure extension is through amine N—H...Ocarboxyl hydrogen bonds between the PABA anions, giving a three-dimensional structure. The crystal structures of (II) and (III) are very similar, the cation–anion pairs being associated only through weak C—H...O hydrogen bonds, giving in both overall two-dimensional layered structures lying parallel to (001). No π–π ring associations are present in any of the structures. |
topic |
crystal structure 1,8-diazabicyclo[5.4.0]undec-7-ene BDU benzoate salts hydrogen bonding |
url |
http://scripts.iucr.org/cgi-bin/paper?S205698901600267X |
work_keys_str_mv |
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