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

ABSTRACT: The title compound, C(12)H(11)BrO(4)S, was synthesized by the oxidation of methyl 2-(5-bromo-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate with 3-chloro-peroxy-benzoic acid. The O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran ring system. The crystal structure is stabilized by C-H⋯π inter-actions, involving a methyl H atom and the benzene ring of a neighbouring mol-ecule, and by weak inter-molecular C-H⋯O hydrogen bonds.

SUBMITTER: Choi HD

PROVIDER: S-EPMC2959898 | biostudies-literature | 2008 Nov

REPOSITORIES: biostudies-literature

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Methyl 2-(5-bromo-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 20081120 Pt 12

The title compound, C(12)H(11)BrO(4)S, was synthesized by the oxidation of methyl 2-(5-bromo-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate with 3-chloro-peroxy-benzoic acid. The O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran ring system. The crystal structure is stabilized by C-H⋯π inter-actions, involving a methyl H atom and the benzene ring of a neighbouring mol-ecule, and by weak inter-molecular C-H⋯O hydrogen bonds. ...[more]

PMID: 21581367

Similar Datasets

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

Project description:In the title compound, C(14)H(15)BrO(4)S, the S atom has a distorted trigonal-pyramidal coordination. The O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The mol-ecules form slightly slipped π-stacked inversion-symmetric dimers by inter-molecular aromatic π-π inter-actions, with a centroid-to-centroid distance of 3.695 (4) Å between the benzene rings of neighbouring mol-ecules. The crystal packing is further stabilized by inter-molecular C-H⋯π inter-actions between the methyl-ene H atoms of the propyl group towards the benzene and furan rings of neighbouring mol-ecules, respectively. Additionally, the crystal structure exhibits weak inter-molecular C-H⋯O hydrogen bonds.

| S-EPMC2968554 | biostudies-literature

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

Project description:In the title compound, C(14)H(15)BrO(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. The crystal structure is stabilized by C-H⋯π inter-actions between a methyl H atom and the benzene ring of a neighbouring mol-ecule, and by weak inter-molecular C-H⋯O hydrogen bonds.

| S-EPMC2959940 | biostudies-literature

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

Project description:In the title compound, C(15)H(17)BrO(4)S, the methyl-sulfinyl O atom and the methyl substituents lie on opposite sides of the plane through the benzofuran fragment. The crystal structure is stabilized by π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.698 (4) Å], and by C-H⋯π inter-actions between a methyl-ene H atom of the butyl group and the benzene ring of the benzofuran system. Additionally, the crystal structure exhibits weak inter-molecular C-H⋯O contacts. The butyl group is disordered over two positions, with site-occupancy factors, from refinement, of 0.720 (8) and 0.280 (8).

| S-EPMC2968244 | biostudies-literature

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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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.

| S-EPMC2960547 | biostudies-literature

5-(4-Bromo-phen-yl)-2-methyl-3-methyl-sulfinyl-1-benzofuran.

Project description:In the title compound, C(16)H(13)BrO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The 4-bromo-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 39.23 (8)°. The crystal structure exhibits weak non-classical inter-molecular C-H⋯O hydrogen bonds and two inter-molecular C-H⋯π inter-actions.

| S-EPMC2969963 | biostudies-literature

5-Bromo-2-(4-methyl-phen-yl)-3-methyl-sulfinyl-1-benzofuran.

Project description:In the title compound, C16H13BrO2S, the 4-methyl-phenyl ring makes a dihedral angle of 29.58 (7)° with the mean plane [r.m.s. deviation = 0.007 (2) Å] of the benzofuran fragment. In the crystal, the molecules are linked by pairs of C-H⋯O hydrogen bonds into centrosymmetric dimers.

| S-EPMC3588837 | biostudies-literature

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.

| S-EPMC2969894 | biostudies-literature

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

Project description:The title compound, C(12)H(11)ClO(4)S, was prepared by the oxidation of methyl 2-(5-chloro-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate with 3-chloro-peroxy-benzoic acid. The O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-to-centroid distance = 3.809 (2) Å], and by C-H⋯π inter-actions between a methyl H atom and the furan ring of an adjacent mol-ecule. In addition, the crystal structure exhibits inter-molecular C-H⋯O hydrogen bonds.

| S-EPMC2959551 | biostudies-literature

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

Project description:The title compound, C(15)H(18)O(4)S, was prepared by the oxidation of isopropyl 2-(5-methyl-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate with 3-chloro-peroxy-benzoic acid. The crystal structure is stabilized by inter-molecular π-π inter-actions between the benzene rings; the centroid-centroid distance between the adjacent benzene rings (symmetry code: ) is 3.713 (2) Å. In addition, C-H⋯π and weak inter-molecular C-H⋯O inter-actions are present in the structure.

| S-EPMC2959682 | biostudies-literature

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