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Methyl 2-[5-(4-hydroxy-phen-yl)-3-methyl-sulfanyl-1-benzofuran-2-yl]acetate.

ABSTRACT: In the title compound, C(18)H(16)O(4)S, the 4-hydroxy-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 34.52?(6)°. The methyl group of the methyl-sulfanyl substituent is almost perpendicular to the plane of the benzofuran fragment [100.90?(8)°] and is slightly tilted towards it. The crystal structure is stabilized by inter-molecular O-H?O hydrogen bonds, and by inter-molecular C-H?? inter-actions between a methyl H atom of the methyl-sulfanyl substituent and the 4-hydroxy-phenyl ring.

SUBMITTER: Choi HD

PROVIDER: S-EPMC2970204 | biostudies-literature | 2009 Sep

REPOSITORIES: biostudies-literature

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Methyl 2-[5-(4-hydroxy-phen-yl)-3-methyl-sulfanyl-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 20090926 Pt 10

In the title compound, C(18)H(16)O(4)S, the 4-hydroxy-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 34.52 (6)°. The methyl group of the methyl-sulfanyl substituent is almost perpendicular to the plane of the benzofuran fragment [100.90 (8)°] and is slightly tilted towards it. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds, and by inter-molecular C-H⋯π inter-actions between a methyl H atom of the methyl-sulfanyl substituent and the 4-h ...[more]

PMID: 21577974

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Isopropyl 2-[5-(4-hydroxy-phen-yl)-3-methyl-sulfanyl-1-benzofuran-2-yl]acetate.

Project description:In the title compound, C(20)H(20)O(4)S, the 4-hydroxy-phenyl ring is rotated out of the plane of the benzofuran unit by 32.87?(8)°. The S-C(meth-yl) bond is almost perpendicular to the plane of the benzofuran fragment [77.8?(1)°] and is slightly tilted towards it. The crystal structure is stabilized by inter-molecular O-H?O and C-H?O hydrogen bonds.

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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?? inter-action between the 5-methyl group and the benzene ring of the benzofuran system.

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2-(4-Fluoro-phen-yl)-3-methyl-sulfanyl-5-phenyl-1-benzofuran.

Project description:In the title compound, C(21)H(15)FOS, the 4-fluoro-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 24.3?(1)°. The dihedral angle between the phenyl ring and the benzofuran plane is 28.3?(1)°. The crystal structure may be stabilized by two very weak aromatic ?-? inter-actions between the furan and the benzene rings of neighbouring benzofuran systems; the centroid-centroid distances are 3.909?(4) and 4.028?(4)?Å.

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2-(3-Fluoro-phen-yl)-3-methyl-sulfanyl-5-phenyl-1-benzofuran.

Project description:In the title compound, C(21)H(15)FOS, the dihedral angles between the mean plane of the benzofuran fragment and the pendant 3-fluoro-phenyl and phenyl rings are 1.76?(5) and 32.29?(5)°, respectively. In the crystal, mol-ecules are linked by a slipped ?-? inter-action between the furan and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.665?(2)?Å, inter-planar distance = 3.391?(2)?Å and slippage = 1.390?(2)?Å].

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2-(4-Chloro-phen-yl)-3-methyl-sulfanyl-5-phenyl-1-benzofuran.

Project description:In the title compound, C(21)H(15)ClOS, the 4-chloro-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 21.50 (6)°. The dihedral angle between the 5-phenyl ring and the benzofuran plane is 29.39 (6)°. The crystal studied was an inversion twin with a 0.65 (7):0.35 (6) domain ratio.

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2,5-Bis(4-fluoro-phen-yl)-2-methyl-sulfanyl-1-benzofuran.

Project description:The crystal studied of the title compound, C(21)H(14)F(2)OS, was an inversion twin with a 0.67?(8):0.33?(8) domain ratio. The 4-fluoro-phenyl ring in the 2-position makes a dihedral angle of 25.14?(6)° with the mean plane of the benzofuran fragment, and the dihedral angle between 4-fluoro-phenyl ring in the 5-position and the mean plane of the benzofuran fragment is 28.50?(7)°. In the crystal, mol-ecules are linked through weak inter-molecular C-H?F and C-H?? inter-actions.

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

Project description:The title compound, C(22)H(15)BrO(3)S, crystallizes with four mol-ecules in the asymmetric unit. The 4-bromo-phenyl rings are rotated out of the benzofuran planes, with dihedral angles for the four mol-ecules of 20.8?(2), 17.8?(2), 23.5?(4) and 23.9?(4)°. The dihedral angles between the 3,4-methyl-ene-dioxy-phenyl ring and the benzofuran plane are 13.5?(2), 7.1?(2), 18.6?(3) and 14.2?(3)° in the four mol-ecules. The crystal structure is stabilized by weak nonclassical inter-molecular C-H?O hydrogen bonds. The crystal structure also exhibits inter-molecular aromatic ?-? inter-actions between the benzene and furan rings and between the 4-bromo-phenyl and 3,4-methyl-enedioxy-phenyl rings from mol-ecules of the same type; the centroid-centroid distances are 3.92?(1) and 3.79?(1), 3.91?(1), 3.77?(1) and 3.77?(1), and 3.79?(1) and 3.75?(1)Å in the four mol-ecules.

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5-(4-Fluoro-phen-yl)-3-methyl-sulfanyl-2-phenyl-1-benzofuran.

Project description:In the title compound, C(21)H(15)FOS, the dihedral angle between the mean plane of the benzofuran fragment and the mean planes of the pendant 4-fluoro-benzene and phenyl rings are 31.72?(6)° and 32.51?(6)°, respectively. In the crystal, the mol-ecules are linked by weak C-H?? inter-actions. The crystal studied was a merohedral twin with a 0.62?(9):0.38?(9) domain ratio.

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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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3-Ethyl-sulfanyl-2-(4-fluoro-phen-yl)-5-phenyl-1-benzofuran.

Project description:In the title compound, C(22)H(17)FOS, the crystal studied was an inversion twin with a 0.42?(18):0.58?(18) domain ratio. The 4-fluoro-phenyl ring is rotated out of the benzofuran plane, making a dihedral angle of 17.82?(6)°, and the dihedral angle between the 5-phenyl ring and the benzofuran plane is 29.45?(7)°.

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