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Ethyl 2-(5-fluoro-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

ABSTRACT: In the title compound, C(13)H(13)FO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The crystal structure exhibits four inter-molecular non-classical C-H?O hydrogen bonds. In addition, the crystal structure contains aromatic ?-? inter-actions between the furan and benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.743?(2)?Å], and two inter-molecular C-H?? inter-actions.

SUBMITTER: Choi HD

PROVIDER: S-EPMC2977135 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature

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Ethyl 2-(5-fluoro-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

Choi Hong Dae HD Seo Pil Ja PJ Son Byeng Wha BW Lee Uk U

Acta crystallographica. Section E, Structure reports online 20090711 Pt 8

In the title compound, C(13)H(13)FO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The crystal structure exhibits four inter-molecular non-classical C-H⋯O hydrogen bonds. In addition, the crystal structure contains aromatic π-π inter-actions between the furan and benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.743 (2) Å], and two inter-molecular C-H⋯π inter-actions. ...[more]

PMID: 21583528

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Methyl 2-(5-fluoro-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

Project description:In the title compound, C(12)H(11)FO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment [O-S-C-C and C-S-C-C torsion angles = 126.70 (13) and -123.55 (13)°, respectively]. The crystal structure is stabilized by weak non-classical inter-molecular C-H⋯O hydrogen-bond inter-actions. The crystal structure also exhibits aromatic π-π stacking inter-actions between furan/benzene and benzene/benzene rings of adjacent benzofuran ring systems [centroid-centroid distances = 3.8258 (9) and 3.8794 (9) Å] and a weak inter-molecular C-H⋯π ring inter-action.

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Project description:In the title compound, C(17)H(14)FIO(2)S, the 3-fluoro-phenyl ring makes a dihedral angle of 14.56?(5)° with the mean plane [r.m.s. deviation = 0.012?(1)?Å] of the benzofuran fragment. In the crystal, mol-ecules are linked via pairs of I?O contacts [3.038?(2)?Å], forming inversion dimers. In the 3-fluoro-phenyl ring, the F atom is disordered over two positions, with site-occupancy factors of 0.747?(3) and 0.253?(3).

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Project description:In the title compound, C(17)H(13)FO(4)S, the 4-fluoro-phenyl ring makes a dihedral angle of 4.92?(4)° with the plane of the 5,6-methyl-enedi-oxy-1-benzofuran fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H?O and C-H?F hydrogen bonds.

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3-Ethyl-sulfinyl-2-(4-fluoro-phen-yl)-5-iodo-7-methyl-1-benzofuran.

Project description:In the title compound, C(17)H(14)FIO(2)S, the 4-fluoro-phenyl ring is rotated out of the benzofuran plane, as indicated by the dihedral angle of 15.60 (6)°. The crystal structure exhibits an I⋯O inter-action [3.052 (2) Å].

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2-Chloro-ethyl 2-(5-bromo-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

Project description:In the title compound, C(13)H(12)BrClO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. There is a mean deviation of 0.016 (4) Å from the least-squares plane defined by the nine constituent benzofuran atoms. The crystal structure is stabilized by aromatic π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.689 (7) Å]and by a weak C-H⋯π interaction between an H atom of the methylene group bonded to the carboxylate O atom and the benzene ring of an adjacent molecule. In addition, the crystal structure exhibits weak non-classical inter-molecular C-H⋯O hydrogen bonds. The chloro-ethyl group is disordered over two positions, with refined site-occupancy factors of 0.767 (6) and 0.233 (6).

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Ethyl 2-(5-bromo-3-ethyl-sulfinyl-1-benzofuran-2-yl)acetate.

Project description:The title compound, C(14)H(15)BrO(4)S, was prepared by the oxidation of ethyl 2-(5-bromo-3-ethyl-sulfanyl-1-benzofuran-2-yl)acetate with 3-chloro-peroxy-benzoic acid. The crystal structure is stabilized by aromatic π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.814 (9) Å], and possibly by weak C-H⋯π inter-actions. In addition, the crystal structure exhibits three inter-molecular C-H⋯O non-classical hydrogen bonds. The ethyl group bonded to carboxyl-ate O atom is disordered over two positions, with refined site-occupancy factors of 0.686 (18) and 0.314 (18).

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Methyl 2-(5-methyl-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

Project description:The title compound, C(13)H(14)O(4)S, was prepared by oxidation of methyl 2-(5-methyl-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate with 3-chloro-peroxy-benzoic acid. The O atom and methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran system. The crystal structure is stabilized by inter-molecular aromatic ?-? inter-actions between the benzene rings of neighbouring mol-ecules, with a centroid-centroid separation of 3.841?(3)?Å.

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