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2-(4-Iodo-phen-yl)-5,7-dimethyl-3-methyl-sulfinyl-1-benzofuran.

ABSTRACT: The title compound, C(17)H(15)IO(2)S, was prepared by the oxidation of 2-(4-iodo-phen-yl)-5,7-dimethyl-3-methyl-sulfanyl-1-benzofuran using 3-chloro-peroxy-benzoic acid. The 4-iodo-phenyl ring makes a dihedral angle of 26.0?(1)° with the plane of the benzofuran fragment, and the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of this plane. The crystal structure is stabilized by inter- and intra-molecular C-H?O hydrogen bonds, and by an I?O halogen bond with an I?O distance of 3.145?(2)?Å and a nearly linear C-I?O angle of 164.01?(9)°.

SUBMITTER: Choi HD

PROVIDER: S-EPMC2961519 | biostudies-literature | 2008 May

REPOSITORIES: biostudies-literature

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2-(4-Iodo-phen-yl)-5,7-dimethyl-3-methyl-sulfinyl-1-benzofuran.

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

Acta crystallographica. Section E, Structure reports online 20080517 Pt 6

The title compound, C(17)H(15)IO(2)S, was prepared by the oxidation of 2-(4-iodo-phen-yl)-5,7-dimethyl-3-methyl-sulfanyl-1-benzofuran using 3-chloro-peroxy-benzoic acid. The 4-iodo-phenyl ring makes a dihedral angle of 26.0 (1)° with the plane of the benzofuran fragment, and the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of this plane. The crystal structure is stabilized by inter- and intra-molecular C-H⋯O hydrogen bonds, and by an I⋯O halogen bond with ...[more]

PMID: 21202603

Similar Datasets

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

Project description:The title compound, C(16)H(13)IO(2)S, was prepared by the oxidation of 2-(4-iodo-phen-yl)-5-methyl-3-methyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The 4-iodo-phenyl ring makes a dihedral angle of 37.97 (9)° with the plane of the benzofuran fragment, and the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of this plane. The mol-ecular packing is stabilized by C-H⋯π inter-actions between H atoms on the 4-iodo-phenyl ring and the benzofuran rings, and by an I⋯O halogen bond of 3.252 (2) Å with a nearly linear C-I⋯O angle of 163.06 (8)°. In addition, the stacked mol-ecules exhibit inversion-related S⋯O contacts [3.209 (2) Å] involving the sulfinyl groups.

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

Project description:In the title compound, C(15)H(10)FIO(2)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 4-iodo-phenyl ring is rotated out of the benzofuran plane by a dihedral angle of 39.4?(1)°. The crystal structure is stabilized by an inter-molecular C-H?O hydrogen bond and an I?O halogen bond [3.055?(2)?Å]. The crystal structure also exhibits an inter-molecular C-H?? inter-action between the methyl H atom and the 4-iodo-phenyl ring of an adjacent benzofuran mol-ecule, and aromatic ?-? inter-actions between the benzene rings of neighbouring benzofuran systems [centroid-centroid distance = 3.558?(3)?Å].

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

Project description:In the title compound, C(17)H(15)IO(2)S, the 4-iodo-phenyl ring makes a dihedral angle of 35.39 (8)° with the plane of the benzofuran fragment. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O and C-H⋯π inter-actions, and an I⋯O contact [3.378 (2) Å]. The crystal structure also exhibits aromatic π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.495 (3) Å].

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

Project description:In the title compound, C(16)H(12)FIO(2)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 4-fluoro-phenyl ring is rotated slightly out of the benzofuran plane, as indicated by the dihedral angle of 7.43?(6)°. In the crystal structure, pairs of short I?O [3.074?(2)?Å] contacts link the mol-ecules into centrosymmetric dimers. These dimers are further linked via aromatic ?-? inter-actions between the benzene and the 4-fluoro-phenyl rings of neighbouring mol-ecules [centroid-centroid distance = 3.617?(3)?Å].

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2-(4-Bromo-phen-yl)-5,7-dimethyl-3-methyl-sulfanyl-1-benzofuran.

Project description:The title compound, C(17)H(15)BrOS, was prepared by the Lewis acid-catalysed reaction of 2,4-dimethyl-phenol with 4'-bromo-2-chloro-2-(methyl-sulfan-yl)acetophenone. The 4-bromo-phenyl ring is rotated slightly out of the benzofuran plane, making a dihedral angle of 8.4 (1)°. The crystal structure is stabilized by a CH(2)-H⋯π inter-action between the 5-methyl group and the benzene ring of the benzofuran system.

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

Project description:In the title compound, C(17)H(14)ClIO(2)S, the 4-chloro-phenyl ring makes a dihedral angle of 12.13?(5)° with the mean plane of the benzofuran ring. In the crystal, pairs of inter-molecular I?O contacts [3.145?(1)?Å] link the mol-ecules into inversion dimers.

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

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

Project description:In the title compound, C(17)H(14)ClIO(2)S, the 4-iodo-phenyl ring makes a dihedral angle of 1.61 (9)° with the benzofuran ring system. In the crystal, mol-ecules are linked through a weak inter-molecular C-H⋯O hydrogen bond and an I⋯O contact [3.416 (2) Å]. The ethyl group is disordered over two orientations with site-occupancy factors of 0.402 (7) and 0.598 (7).

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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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Methyl 2-(5-iodo-7-methyl-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

Project description:There are two symmetry-independent mol-ecules in the asymmetric unit of the title compound, C(13)H(13)IO(4)S. In each mol-ecule, 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 and furan ring [centroid-centroid distance = 3.866 (7) Å], and by inter-molecular C-H⋯π inter-actions and a sulfin-yl-sulfinyl inter-action [S⋯O = 3.025 (4) Å]. The crystal structure also exhibits weak inter-molecular C-H⋯O hydrogen bonds and two different I⋯O halogen bonds.

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