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Different packing motifs in the crystal structures of three mol-ecular salts containing the 2-amino-5-carb-oxy-anilinium cation: C7H9N2O2 +·Cl-, C7H9N2O2 +·Br- and C7H9N2O2 +·NO3 -·H2O.

ABSTRACT: The syntheses and crystal structures of three mol-ecular salts of protonated 3,4-di-amino-benzoic acid, viz. 2-amino-5-carb-oxy-anilinium chloride, C7H9N2O2 +·Cl-, (I), 2-amino-5-carb-oxy-anilinium bromide, C7H9N2O2 +·Br-, (II), and 2-amino-5-carb-oxy-anilinium nitrate monohydrate, C7H9N2O2 +·NO3 -·H2O, (III), are described. The cation is protonated at the meta-N atom (with respect to the carb-oxy group) in each case. In the crystal of (I), carb-oxy-lic acid inversion dimers linked by pairwise O-H?O hydrogen bonds are seen and each N-H group forms a hydrogen bond to a chloride ion to result in (100) undulating layers of chloride ions bridged by the inversion dimers into a three-dimensional network. The extended structure of (II) features O-H?Br, N-H?Br and N-H?O hydrogen bonds: the last of these generates C(7) chains of cations. Overall, the packing in (II) features undulating (100) sheets of bromide ions alternating with the organic cations. Inter-molecular inter-actions in the crystal of (III) include O-H?O, O-H?(O,O), N-H?O, N-H?N and O-H?N links. The cations are linked into (001) sheets, and the nitrate ions and water mol-ecules form undulating chains. Taken together, alternating (001) slabs of organic cations plus anions/water mol-ecules result. Hirshfeld surfaces and fingerprint plots were generated to give further insight into the inter-molecular inter-actions in these structures. The crystal used for the data collection of (II) was twinned by rotation about [100] in reciprocal space in a 0.4896?(15):0.5104?(15) ratio.

SUBMITTER: Mukombiwa ET

PROVIDER: S-EPMC7133033 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Different packing motifs in the crystal structures of three mol-ecular salts containing the 2-amino-5-carb-oxy-anilinium cation: C7H9N2O2 +·Cl-, C7H9N2O2 +·Br- and C7H9N2O2 +·NO3 -·H2O.

Mukombiwa Edson T ET Harrison William T A WTA

Acta crystallographica. Section E, Crystallographic communications 20200313 Pt 4

The syntheses and crystal structures of three mol-ecular salts of protonated 3,4-di-amino-benzoic acid, viz. 2-amino-5-carb-oxy-anilinium chloride, C7H9N2O2 +·Cl-, (I), 2-amino-5-carb-oxy-anilinium bromide, C7H9N2O2 +·Br-, (II), and 2-amino-5-carb-oxy-anilinium nitrate monohydrate, C7H9N2O2 +·NO3</su ...[more]

PMID: 32280498

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Project description:The syntheses and structures of five mol-ecular salts of protonated 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine (C11H19N2S+) with different deprotonated carb-oxy-lic acids (4-methyl-benzoic acid, 4-bromo-benzoic acid, 3,5-di-nitro-benzoic acid, fumaric acid and succinic acid) are reported, namely 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-methyl-benzoate, C11H19N2S+·C8H7O2 -, (I), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 4-bromo-benzoate, C11H19N2S+·C7H4BrO2 -, (II), 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium 3,5-di-nitro-benzoate, C11H19N2S+·C7H3N2O6 -, (III), bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) fumarate, 2C11H19N2S+·C4H2O4 2-,(IV), and the 1:1 co-crystal of bis-(2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium) succinate and 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium hydrogen succin-ate 4,4,7,7-tetra-methyl-3a,5,6,7a-tetra-hydro-benzo-thia-zol-2-yl-amine, 1.5C11H19N2S+·0.5C4H4O4 2-·0.5C4H5O4 -. 0.5C11H18N2S, (V). In every case, the cation protonation occurs at the N atom of the thia-zole ring and the six-membered ring adopts a half-chair conformation (in some cases, the deviating methyl-ene groups are disordered over two sets of sites). The C-N bond lengths of the nominal -NH+=C-NH2 fragment of the cation are indistinguishable, indicating a significant contribution of the -NH-C=N+H2 resonance form to the structure. The packing for (I)-(V) features a robust local R 2 2(8) loop motif in which the cation forms two near-linear N-H?O hydrogen bonds from the N+-H group and syn H atom of the amine group to the carboxyl-ate group of an adjacent anion [(V) shows disorder of one of these bonds over N-H?O and N?H-O contributors but the same R 2 2(8) loop results for both disorder components]. The anti H atom of the -NH2 group also forms an N-H?O hydrogen bond, which results in [001] chains in (I) and (II), isolated centrosymmetric tetra-mers in (III) and [100] chains in (IV) and (V). Hirshfeld fingerprint plots and contact percentages for the different types of contacts of the cations are discussed.

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Different packing motifs in the crystal structures of three mol-ecular salts containing the 2-amino-5-carb-oxy-anilinium cation: C7H9N2O2 +·Cl-, C7H9N2O2 +·Br- and C7H9N2O2 +·NO3 -·H2O.

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