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Two closely related 2-(benzo-furan-2-yl)-2-oxoethyl benzoates: structural differences and C-H?O hydrogen-bonded supra-molecular assemblies.

ABSTRACT: The compounds 2-(1-benzo-furan-2-yl)-2-oxoethyl 2-nitro-benzoate, C₁₇H₁₁NO₆ (I), and 2-(1-benzo-furan-2-yl)-2-oxoethyl 2-amino-benzoate, C₁₇H₁₃NO₄ (II), were synthesized under mild conditions. Their mol-ecular structures were characterized by both spectroscopic and single-crystal X-ray diffraction analysis. The mol-ecular conformations of both title compounds are generally similar. However, different ortho-substituted moieties at the phenyl ring of the two compounds cause deviations in the torsion angles between the carbonyl group and the attached phenyl ring. In compound (I), the ortho-nitro-phenyl ring is twisted away from the adjacent carbonyl group whereas in compound (II), the ortho-amino-phenyl ring is almost co-planar with the carbonyl group. In the crystal of compound (I), two C-H?O hydrogen bonds link the mol-ecules into chains propagating along the c-axis direction and the chains are inter-digitated, forming sheets parallel to [20-1]. Conversely, pairs of N-H?O hydrogen bonds in compound (II) link inversion-related mol-ecules into dimers, which are further extended by C-H?O hydrogen bonds into dimer chains. These chains are inter-connected by ?-? inter-actions involving the furan rings, forming sheets parallel to the ac plane.

SUBMITTER: Then LY

PROVIDER: S-EPMC5499297 | biostudies-literature | 2017 Jul

REPOSITORIES: biostudies-literature

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Two closely related 2-(benzo-furan-2-yl)-2-oxoethyl benzoates: structural differences and C-H⋯O hydrogen-bonded supra-molecular assemblies.

Then Li Yee LY Chidan Kumar C S CS Kwong Huey Chong HC Win Yip-Foo YF Mah Siau Hui SH Quah Ching Kheng CK Naveen S S Warad Ismail I

Acta crystallographica. Section E, Crystallographic communications 20170630 Pt 7

The compounds 2-(1-benzo-furan-2-yl)-2-oxoethyl 2-nitro-benzoate, C17H11NO6 (I), and 2-(1-benzo-furan-2-yl)-2-oxoethyl 2-amino-benzoate, C17H13NO4 (II), were synthesized under mild conditions. Their mol-ecular structures were characterized by both spectroscopic and single-crystal X-ray diffraction analysis. The mol-ecular conformations of both title compounds are generally similar. However, different ortho-substituted moiet ...[more]

PMID: 28775889

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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.

Dataset Information

Two closely related 2-(benzo-furan-2-yl)-2-oxoethyl benzoates: structural differences and C-H?O hydrogen-bonded supra-molecular assemblies.

Publications

Two closely related 2-(benzo-furan-2-yl)-2-oxoethyl benzoates: structural differences and C-H⋯O hydrogen-bonded supra-molecular assemblies.

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