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5-Iodo-2,7-dimethyl-3-phenyl-sulfinyl-1-benzofuran.

ABSTRACT: The title compound, C(16)H(13)IO(2)S, was prepared by the oxidation of 5-iodo-2,7-dimethyl-3-phenyl-sulfanyl-1-benzofuran using 3-chloro-perbenzoic acid. The O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran system. The phenyl ring is nearly perpendicular to the plane of the benzofuran fragment [89.15?(5)°]. The crystal structure is stabilized by an I?O halogen bond [I?O = 3.177?(2)?Å and C-I?O = 175.68?(6)°] linking mol-ecules into centrosymmetric dimers and by a weak C-H?? inter-action between a phenyl H atom and the furan ring of the benzofuran system.

SUBMITTER: Choi HD

PROVIDER: S-EPMC2960312 | biostudies-literature | 2008 Jan

REPOSITORIES: biostudies-literature

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5-Iodo-2,7-dimethyl-3-phenyl-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 20080123 Pt 2

The title compound, C(16)H(13)IO(2)S, was prepared by the oxidation of 5-iodo-2,7-dimethyl-3-phenyl-sulfanyl-1-benzofuran using 3-chloro-perbenzoic acid. The O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran system. The phenyl ring is nearly perpendicular to the plane of the benzofuran fragment [89.15 (5)°]. The crystal structure is stabilized by an I⋯O halogen bond [I⋯O = 3.177 (2) Å and C-I⋯O = 175.68 (6)°] linking mol-ecules in ...[more]

PMID: 21201509

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5-Iodo-2,7-dimethyl-3-phenyl-sulfonyl-1-benzofuran.

Project description:The title compound, C(16)H(13)IO(3)S, was prepared by the oxidation of 5-iodo-2,7-dimethyl-3-phenyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 76.31 (8)° with the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic π-π inter-actions between the furan and benzene rings of neighbouring mol-ecules, and between the benzene rings of neighbouring mol-ecules; the centroid-centroid distances within the stack are 3.700 (4) and 3.788 (4) Å. In addition, the crystal structure exhibits inter- and intra-molecular C-H⋯O inter-actions, and an I⋯O halogen bond with an I⋯O distance of 3.282 (2) Å and a nearly linear C-I⋯O angle of 165.69 (8)°.

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Project description:In the title compound, C(17)H(15)IO(3)S, the 4-methyl-phenyl ring makes a dihedral angle of 76.95?(5)° with the mean plane [r.m.s. deviation = 0.019?(2)?Å] of the benzofuran fragment. In the crystal, mol-ecules are linked via pairs of C-H?O hydrogen bonds, forming inversion dimers. These dimers are connected by slipped ?-? inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.671?(3)?Å and slippage = 1.049?(3)?Å].

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Project description:In the title compound, C(16)H(12)FIO(3)S, the 4-fluoro-phenyl ring makes a dihedral angle of 72.31?(6)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H?O hydrogen bonds, and by an I?I contact [3.7764?(3)?Å]. The crystal structure also exhibits a weak C-I?? [3.901?(3)?Å] inter-action and a slipped ?-? inter-action between the furan and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.845?(3), inter-planar distance = 3.555?(3) and slippage = 1.465?(3)?Å].

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Project description:In the title compound, C(16)H(12)FlO(2)S, the 4-fluoro-phenyl ring makes a dihedral angle of 80.21?(6)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked through weak inter-molecular C-H?O hydrogen bonds. The crystal structure also exhibits an inter-molecular I?F contact [3.423?(2)?Å].

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5-Bromo-3-cyclo-pentyl-sulfinyl-2,7-dimethyl-1-benzofuran.

Project description:In the title compound, C(15)H(17)BrO(2)S, the cyclo-pentyl ring adopts an envelope conformation. In the crystal, mol-ecules are linked by weak C-H?O hydrogen bonds. A slipped ?-? inter-action occurs between the furan and benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.892?(3)?Å and slippage = 1.786?(3)?Å]. The crystal structure also exhibits a weak C-Br?? [2.919?(3)?Å] inter-action.

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5-Chloro-3-cyclo-hexyl-sulfinyl-2,7-dimethyl-1-benzofuran.

Project description:In the title compound, C(16)H(19)ClO(2)S, the cyclo-hexyl ring adopts a chair conformation and the aryl-sulfinyl unit is positioned equatorial relative to the cyclo-hexyl group. The least-squares plane through all six C atoms of the cyclo-hexyl ring makes a dihedral angle of 74.80 (6)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked through inter-molecular C-H⋯O hydrogen bonds.

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5-Bromo-3-cyclo-hexyl-sulfinyl-2,7-dimethyl-1-benzofuran.

Project description:In the title compound, C(16)H(19)BrO(2)S, the cyclo-hexyl ring adopts a chair conformation. In the crystal, mol-ecules are linked by a Br⋯Br [3.5994 (5) Å] contact and a C-H⋯π inter-action involving the phenyl ring of the benzofuran. The crystal structure also exhibits a slipped π-π inter-action between the furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.767 (1) Å and inter-planar distance of 3.452 (1) Å with a slippage of 1.508 Å].

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