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

ABSTRACT: In the title compound, C(15)H(17)IO(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 weak inter-molecular C-H?? inter-actions between a methyl H atom of the methyl-sulfinyl group and the benzene ring of the benzofuran system, and by an I?O halogen bond of 3.173?(3)?Å and a nearly linear C-I?O angle of 171.7?(1)°. In addition, the crystal structure exhibits weak inter-molecular C-H?O hydrogen bonds. The O atom of the carbonyl group and the butyl chain are both disordered over two positions with site-occupancy factors from refinement of 0.55?(4) and 0.45?(4) (for the O atom), and 0.76?(2) and 0.24?(2) (for the butyl group).

SUBMITTER: Choi HD

PROVIDER: S-EPMC2968330 | biostudies-literature | 2009 Jan

REPOSITORIES: biostudies-literature

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Butyl 2-(5-iodo-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 20090108 Pt 2

In the title compound, C(15)H(17)IO(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 weak inter-molecular C-H⋯π inter-actions between a methyl H atom of the methyl-sulfinyl group and the benzene ring of the benzofuran system, and by an I⋯O halogen bond of 3.173 (3) Å and a nearly linear C-I⋯O angle of 171.7 (1)°. In addition, the crystal structure exhibits weak inter-molec ...[more]

PMID: 21581881

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

Project description:In the title compound, C(14)H(15)IO(4)S, 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 inter-molecular C-H?? inter-actions between an H atom of the propyl methyl-ene group closest to the carboxyl-ate O atom and the benzene ring of a neighbouring mol-ecule, and between an H atom of the outer propyl methyl-ene group and the furan ring of a neighbouring mol-ecule, respectively. Additionally, the crystal structure exhibits inter-molecular C-H?O hydrogen bonds.

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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?? 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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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 ?-? inter-actions between the benzene and furan ring [centroid-centroid distance = 3.866?(7)?Å], and by inter-molecular C-H?? 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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Isopropyl 2-(5-iodo-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

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

Project description:In the title mol-ecule, C(15)H(17)IO(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. In the crystal structure, inter-molecular I?O [2.994?(3)?Å] halogen bonding links the mol-ecules into centrosymmetric dimers, which are further packed into ribbons along the c axis by inter-molecular sulfin-yl-sulfinyl inter-actions [S?O 3.128?(3)?Å].

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

Project description: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)°.

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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?? inter-actions, and an I?O contact [3.378?(2)?Å]. The crystal structure also exhibits aromatic ?-? inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.495?(3)?Å].

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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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