Role of pKa in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids

The structures of the six hydrogen-bonded 1:1 compounds of 4-methylquinoline (C10H9N) with chloro- and nitro-substituted benzoic acids (C7H4ClNO4), namely, 4-methylquinolinium 2-chloro-4-nitrobenzoate, C10H10N+·C7H3ClNO4−, (I), 4-methylquinoline–2-chloro-5-nitrobenzoic acid (1/1), C10H9N·C7H4ClNO4,...

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Autor principal:	Hiroyuki Ishida
Formato:	article
Lenguaje:	EN
Publicado:	International Union of Crystallography 2021
Materias:	crystal structure 2-chloro-4-nitrobenzoic acid 2-chloro-5-nitrobenzoic acid 2-chloro-6-nitrobenzoic acid 3-chloro-2-nitrobenzoic acid 4-chloro-2-nitrobenzoic acid 5-chloro-2-nitrobenzoic acid 4-methylquinoline hydrogen bond disorder hirshfeld surface Chemistry QD1-999
Acceso en línea:	https://doaj.org/article/c800f519a1f047fc9d5c5a3f4a871ef1
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spelling	oai:doaj.org-article:c800f519a1f047fc9d5c5a3f4a871ef12021-11-12T11:16:09ZRole of pKa in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids2056-989010.1107/S2056989021010896https://doaj.org/article/c800f519a1f047fc9d5c5a3f4a871ef12021-11-01T00:00:00Zhttp://scripts.iucr.org/cgi-bin/paper?S2056989021010896https://doaj.org/toc/2056-9890The structures of the six hydrogen-bonded 1:1 compounds of 4-methylquinoline (C10H9N) with chloro- and nitro-substituted benzoic acids (C7H4ClNO4), namely, 4-methylquinolinium 2-chloro-4-nitrobenzoate, C10H10N+·C7H3ClNO4−, (I), 4-methylquinoline–2-chloro-5-nitrobenzoic acid (1/1), C10H9N·C7H4ClNO4, (II), 4-methylquinolinium 2-chloro-6-nitrobenzoate, C10H9.63N0.63+·C7H3.37ClNO40.63−, (III), 4-methylquinolinium 3-chloro-2-nitrobenzoate, C10H9.54N0.54+·C7H3.46ClNO40.54−, (IV), 4-methylquinolinium 4-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4−, (V), and 4-methylquinolinium 5-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4−, have been determined at 185–190 K. In each compound, the acid and base molecules are linked by a short hydrogen bond between a carboxy (or carboxylate) O atom and an N atom of the base. The O...N distances are 2.5652 (14), 2.556 (3), 2.5485 (13), 2.5364 (13), 2.5568 (13) and 2.5252 (11) Å, respectively, for compounds (I)–(VI). In the hydrogen-bonded acid–base units of (III) and (IV), the H atoms are each disordered over two positions with O site:N site occupancies of 0.37 (3):0.63 (3) and 0.46 (3):0.54 (4), respectively, for (III) and (IV). The H atoms in the hydrogen-bonded units of (I), (V) and (VI) are located at the N-atom site, while the H atom in (II) is located at the O-atom site. In all the crystals of (I)–(VI), π–π stacking interactions between the quinoline ring systems and C—H...O hydrogen bonds are observed. Similar layer structures are constructed in (IV)–(VI) through these interactions together with π–π interactions between the benzene rings of the adjacent acid molecules. A short Cl...Cl contact and an N—O...π interaction are present in (I), while a C—H...Cl hydrogen bond and a π–π interaction between the benzene ring of the acid molecule and the quinoline ring system in (II), and a C—H...π interaction in (III) are observed. Hirshfeld surfaces for the title compounds mapped over dnorm and shape index were generated to visualize the weak intermolecular interactions.Hiroyuki IshidaInternational Union of Crystallographyarticlecrystal structure2-chloro-4-nitrobenzoic acid2-chloro-5-nitrobenzoic acid2-chloro-6-nitrobenzoic acid3-chloro-2-nitrobenzoic acid4-chloro-2-nitrobenzoic acid5-chloro-2-nitrobenzoic acid4-methylquinolinehydrogen bonddisorderhirshfeld surfaceChemistryQD1-999ENActa Crystallographica Section E: Crystallographic Communications, Vol 77, Iss 11, Pp 1144-1152 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	crystal structure 2-chloro-4-nitrobenzoic acid 2-chloro-5-nitrobenzoic acid 2-chloro-6-nitrobenzoic acid 3-chloro-2-nitrobenzoic acid 4-chloro-2-nitrobenzoic acid 5-chloro-2-nitrobenzoic acid 4-methylquinoline hydrogen bond disorder hirshfeld surface Chemistry QD1-999
spellingShingle	crystal structure 2-chloro-4-nitrobenzoic acid 2-chloro-5-nitrobenzoic acid 2-chloro-6-nitrobenzoic acid 3-chloro-2-nitrobenzoic acid 4-chloro-2-nitrobenzoic acid 5-chloro-2-nitrobenzoic acid 4-methylquinoline hydrogen bond disorder hirshfeld surface Chemistry QD1-999 Hiroyuki Ishida Role of pKa in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids
description	The structures of the six hydrogen-bonded 1:1 compounds of 4-methylquinoline (C10H9N) with chloro- and nitro-substituted benzoic acids (C7H4ClNO4), namely, 4-methylquinolinium 2-chloro-4-nitrobenzoate, C10H10N+·C7H3ClNO4−, (I), 4-methylquinoline–2-chloro-5-nitrobenzoic acid (1/1), C10H9N·C7H4ClNO4, (II), 4-methylquinolinium 2-chloro-6-nitrobenzoate, C10H9.63N0.63+·C7H3.37ClNO40.63−, (III), 4-methylquinolinium 3-chloro-2-nitrobenzoate, C10H9.54N0.54+·C7H3.46ClNO40.54−, (IV), 4-methylquinolinium 4-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4−, (V), and 4-methylquinolinium 5-chloro-2-nitrobenzoate, C10H10N+·C7H3ClNO4−, have been determined at 185–190 K. In each compound, the acid and base molecules are linked by a short hydrogen bond between a carboxy (or carboxylate) O atom and an N atom of the base. The O...N distances are 2.5652 (14), 2.556 (3), 2.5485 (13), 2.5364 (13), 2.5568 (13) and 2.5252 (11) Å, respectively, for compounds (I)–(VI). In the hydrogen-bonded acid–base units of (III) and (IV), the H atoms are each disordered over two positions with O site:N site occupancies of 0.37 (3):0.63 (3) and 0.46 (3):0.54 (4), respectively, for (III) and (IV). The H atoms in the hydrogen-bonded units of (I), (V) and (VI) are located at the N-atom site, while the H atom in (II) is located at the O-atom site. In all the crystals of (I)–(VI), π–π stacking interactions between the quinoline ring systems and C—H...O hydrogen bonds are observed. Similar layer structures are constructed in (IV)–(VI) through these interactions together with π–π interactions between the benzene rings of the adjacent acid molecules. A short Cl...Cl contact and an N—O...π interaction are present in (I), while a C—H...Cl hydrogen bond and a π–π interaction between the benzene ring of the acid molecule and the quinoline ring system in (II), and a C—H...π interaction in (III) are observed. Hirshfeld surfaces for the title compounds mapped over dnorm and shape index were generated to visualize the weak intermolecular interactions.
format	article
author	Hiroyuki Ishida
author_facet	Hiroyuki Ishida
author_sort	Hiroyuki Ishida
title	Role of pKa in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids
title_short	Role of pKa in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids
title_full	Role of pKa in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids
title_fullStr	Role of pKa in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids
title_full_unstemmed	Role of pKa in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids
title_sort	role of pka in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids
publisher	International Union of Crystallography
publishDate	2021
url	https://doaj.org/article/c800f519a1f047fc9d5c5a3f4a871ef1
work_keys_str_mv	AT hiroyukiishida roleofpkainestablishingthecrystalstructuresofsixhydrogenbondedcompoundsof4methylquinolinewithdifferentisomersofchloroandnitrosubstitutedbenzoicacids
_version_	1718430643650560000

Role of pKa in establishing the crystal structures of six hydrogen-bonded compounds of 4-methylquinoline with different isomers of chloro- and nitro-substituted benzoic acids

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