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Role of pK _a in establishing the crystal structures of six hydrogen-bonded compounds of 4-methyl-quinoline with different isomers of chloro- and nitro-substituted benzoic acids.

ABSTRACT: The structures of the six hydrogen-bonded 1:1 compounds of 4-methyl-quinoline (C₁₀H₉N) with chloro- and nitro-substituted benzoic acids (C₇H₄ClNO₄), namely, 4-methyl-quinolinium 2-chloro-4-nitro-benzoate, C₁₀H₁₀N⁺·C₇H₃ClNO₄ ^-, (I), 4-methyl-quinoline-2-chloro-5-nitro-benzoic acid (1/1), C₁₀H₉N·C₇H₄ClNO₄, (II), 4-methyl-quinolinium 2-chloro-6-nitro-benzoate, C₁₀H_9.63N^0.63+·C₇H_3.37ClNO₄ ^0.63-, (III), 4-methyl-quinolinium 3-chloro-2-nitro-benzoate, C₁₀H_9.54N^0.54+·C₇H_3.46ClNO₄ ^0.54-, (IV), 4-methyl-quinolinium 4-chloro-2-nitro-benzoate, C₁₀H₁₀N⁺·C₇H₃ClNO₄ ^-, (V), and 4-methyl-quinolinium 5-chloro-2-nitro-benzoate, C₁₀H₁₀N⁺·C₇H₃ClNO₄ ^-, have been determined at 185-190 K. In each compound, the acid and base mol-ecules are linked by a short hydrogen bond between a carb-oxy (or carboxyl-ate) 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 inter-actions between the quinoline ring systems and C-H⋯O hydrogen bonds are observed. Similar layer structures are constructed in (IV)-(VI) through these inter-actions together with π-π inter-actions between the benzene rings of the adjacent acid mol-ecules. A short Cl⋯Cl contact and an N-O⋯π inter-action are present in (I), while a C-H⋯Cl hydrogen bond and a π-π inter-action between the benzene ring of the acid mol-ecule and the quinoline ring system in (II), and a C-H⋯π inter-action in (III) are observed. Hirshfeld surfaces for the title compounds mapped over d _norm and shape index were generated to visualize the weak inter-molecular inter-actions.

SUBMITTER: Ishida H

PROVIDER: S-EPMC8587989 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Role of pK a in establishing the crystal structures of six hydrogen-bonded compounds of 4-methyl-quinoline with different isomers of chloro- and nitro-substituted benzoic acids.

Ishida Hiroyuki H

Acta crystallographica. Section E, Crystallographic communications 20211026 Pt 11

The structures of the six hydrogen-bonded 1:1 compounds of 4-methyl-quinoline (C10H9N) with chloro- and nitro-substituted benzoic acids (C7H4ClNO4), namely, 4-methyl-quinolinium 2-chloro-4-nitro-benzoate, C10H10N+·C7H3ClNO4 -, (I), 4-methyl-quinoline-2-chloro-5-nitro-benzoic acid (1/1), C10H9N·C7H4ClNO4, (II), 4 ...[more]

PMID: 34868653

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Project description:The crystal structures of two erbium(III) complexes with 4-amino-benzoic acid (4-ABAH), namely bis-(μ2-4-amino-benzoato-κ(2) O:O')bis-[bis(4-amino-benzoato-κ(2) O,O')di-aqua-erbium(III)] dihydrate, [Er2(C7H6NO2)6(H2O)4]·2H2O, (I), and 4-chloro-3-nitro-benzoic acid (CLNBAH), namely poly[hexa-kis-(μ2-4-chloro-3-nitro-benzoato-κ(2) O:O')bis-(dimethyl sulfoxide-κO)dierbium(III)], [Er2(C7H3ClNO4)6(C2H6OS)2] n , (II), have been determined. In the structure of solvatomorphic compound (I), the symmetry-related irregular ErO8 coordination polyhedra in the discrete centrosymmetric dinuclear complex comprise two monodentate water mol-ecules and six carboxyl-ate O-atom donors, four from two bidentate carboxyl-ate O,O'-chelate groups and two from the bis-monodentate O:O'-bridging group of the third 4-ABA anion. The Er-O bond-length range is 2.232 (3)-2.478 (3) Å and the Er⋯Er separation in the dinuclear complex unit is 4.7527 (4) Å. One of the coordinating water mol-ecules is involved in an intra-unit O-H⋯O hydrogen-bonding association with an inversion-related carboxyl-ate O-atom acceptor. In contrast, the anhydrous compound (II) is polymeric, based on centrosymmetric dinuclear repeat units comprising ErO7 coordination polyhedra which involve four O-atom donors from two bidentate O:O'-bridging carboxyl-ate groups, one O-atom donor from the monodentate dimethyl sulfoxide ligand and two O-atom donors from the third bridging CLNBA anion. The latter provides the inter-unit link in the one-dimensional coordination polymer extending along [100]. The Er-O bond-length range in (II) is 2.239 (6)-2.348 (6) Å and the Er⋯Er separation within the dinuclear unit is 4.4620 (6) Å. In the crystal of (I), extensive inter-dimer O-H⋯O and N-H⋯O hydrogen-bonding inter-actions involving both the coordinating water mol-ecules and the solvent water mol-ecules, as well as the amine groups of the 4-ABA anions, give an overall three-dimensional network structure. Within this structure are also weak π-π ring inter-actions between two of the coordinating ligands [ring-centroid separations = 3.676 (3) and 3.711 (2) Å]. With (II), only weak intra-polymer C-H⋯O, C-H⋯Cl and C-H⋯S inter-actions are present.

Dataset Information

Role of pK _a in establishing the crystal structures of six hydrogen-bonded compounds of 4-methyl-quinoline with different isomers of chloro- and nitro-substituted benzoic acids.

Publications

Role of p<i>K</i> <sub>a</sub> in establishing the crystal structures of six hydrogen-bonded compounds of 4-methyl-quinoline with different isomers of chloro- and nitro-substituted benzoic acids.

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