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5-Bromo-3-cyclo-hexyl-sulfinyl-2,4,6-trimethyl-1-benzo-furan.

ABSTRACT: In the title compound, C17H21BrO2S, the cyclo-hexyl ring adopts a chair conformation and the aryl-sulfinyl unit is positioned equatorially relative to the cyclo-hexyl group. The benzo-furan unit is essentially planar, with an r.m.s. deviation of 0.016?(2)?Å. In the crystal, mol-ecules are linked by weak C-H?O, C-H?? and Br?? [3.663?(2)?Å] inter-actions, resulting in a three-dimensional network. A Br?Br [3.6838?(6)?Å] contact is observed. The O atom of the sulfinyl group is disordered over two orientations with an occupancy ratio of 0.863?(5):0.137?(5).

SUBMITTER: Choi HD

PROVIDER: S-EPMC3998487 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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5-Bromo-3-cyclo-hexyl-sulfinyl-2,4,6-trimethyl-1-benzo-furan.

Choi Hong Dae HD Seo Pil Ja PJ Lee Uk U

Acta crystallographica. Section E, Structure reports online 20140215 Pt 3

In the title compound, C17H21BrO2S, the cyclo-hexyl ring adopts a chair conformation and the aryl-sulfinyl unit is positioned equatorially relative to the cyclo-hexyl group. The benzo-furan unit is essentially planar, with an r.m.s. deviation of 0.016 (2) Å. In the crystal, mol-ecules are linked by weak C-H⋯O, C-H⋯π and Br⋯π [3.663 (2) Å] inter-actions, resulting in a three-dimensional network. A Br⋯Br [3.6838 (6) Å] contact is observed. The O atom of the sulfinyl group is disordered over two or ...[more]

PMID: 24765011

Similar Datasets

Crystal structure of 5-chloro-3-cyclo-hexyl-sulfinyl-2,4,6-trimethyl-1-benzo-furan.

Project description:In the title compound, C17H21ClO2S, the cyclo-hexyl ring adopts a chair conformation with the C-S bond in an equatorial orientation. In the crystal, mol-ecules are linked by C-H?O and C-H?? hydrogen bonds and a Cl?? [3.594?(2)?Å] contact into chains along the a-axis direction.

| S-EPMC4186066 | biostudies-literature

5-Cyclo-hexyl-3-ethyl-sulfinyl-2-(3-fluoro-phen-yl)-1-benzo-furan.

Project description:In the title compound, C22H23FO2S, the cyclo-hexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.013?(2)?Å] of the benzo-furan ring system and the mean plane [r.m.s. deviation = 0.009?(2)?Å] of the 3-fluoro-phenyl ring is 24.80?(4)°. In the crystal, mol-ecules are connected by C-H?O hydrogen bonds, forming chains along [10-1]. These chains are linked via C-H?F hydrogen bonds, forming a three-dimensional structure. There are also inter-planar inter-actions present involving the furan ring of the benzo-furan ring system and the 3-fluoro-phenyl ring [centroid-centroid distance = 3.728?(2)?Å].

| S-EPMC3884386 | biostudies-literature

5-Cyclo-hexyl-2-(4-fluoro-phen-yl)-3-phenyl-sulfinyl-1-benzo-furan.

Project description:The asymmetric unit of the title compound, C26H23FO2S, contains two independent mol-ecules (A and B), in both of which the cyclo-hexyl ring adopts a chair conformation. The benzo-furan ring systems, the 4-fluoro-phenyl and phenyl rings are essentially planar, with r.m.s. deviations of 0.008?(1), 0.002?(1) and 0.003?(1)?Å, respectively, for mol-ecule A, and 0.016?(1), 0.004?(1) and 0.002?(1)?Å, respectively, for mol-ecule B. The dihedral angles between the benzo-furan ring system and the pendant 4-fluoro-phenyl and phenyl rings are 12.3?(7) and 85.42?(4)°, respectively, for mol-ecule A, and 39.67?(6) and 72.17?(4)°, respectively, for mol-ecule B. In the crystal, mol-ecules are linked by weak C-H?O and C-H?? inter-actions, resulting in a three-dimensional network.

| S-EPMC3884427 | biostudies-literature

5-Cyclo-hexyl-2-(2-fluoro-phen-yl)-3-methyl-sulfinyl-1-benzo-furan.

Project description:In the title compound, C21H21FO2S, the cyclo-hexyl ring adopts a chair conformation. The 2-fluoro-benzene ring makes a dihedral angle of 38.68 (6)° with the mean plane [r.m.s. deviation = 0.018 (2) Å] of the benzo-furan fragment. In the crystal, mol-ecules are linked by pairs of C-H⋯O hydrogen bonds into dimers, which are further packed into stacks along the c axis by C-H⋯O hydrogen bonds. In addition, the stacked mol-ecules exhibit S⋯O contacts [3.1733 (13) Å] involving the sulfinyl groups. The F atom is disordered over two positions, with site-occupancy factors of 0.961 (3) and 0.039 (3).

| S-EPMC3685044 | biostudies-literature

5-Bromo-2,4,6-trimethyl-3-(4-methyl-phenyl-sulfin-yl)-1-benzo-furan.

Project description:In the title compound, C18H17BrO2S, the dihedral angle between the methyl-phenyl ring and the mean plane of the benzo-furan rung system is 87.0 (2)°. In the crystal, mol-ecules related by inversion are paired into dimers via C-H⋯O and C-H⋯π inter-actions. These dimers are further linked by C-H⋯O hydrogen bonds and π-π inter-actions between the benzene and furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.555 (5) Å], resulting in a three-dimensional supra-molecular network.

| S-EPMC3998541 | biostudies-literature

5-Bromo-2,4,6-trimethyl-3-(3-methyl-phenyl-sulfin-yl)-1-benzo-furan.

Project description:In the title compound, C18H17BrO2S, the dihedral angle between the mean plane of the benzo-furan ring system and the benzene ring is 68.58 (4)°. In the crystal, mol-ecules are linked via pairs of C-H⋯O hydrogen bonds into inversion dimers. These dimers are linked by C-H⋯O hydrogen bonds and π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.783 (1) Å], forming a three-dimensional network. In addition, the stacked mol-ecules exhibit inversion-related S⋯O contacts [3.153 (1) Å] involving the sulfinyl groups.

| S-EPMC3998578 | biostudies-literature

2,5,7-Trimethyl-3-phenyl-sulfinyl-1-benzo-furan.

Project description:The title compound, C(17)H(16)O(2)S, was prepared by the oxidation of 2,5,7-trimethyl-3-phenyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The phenyl ring is nearly perpendicular to the plane of the benzofuran unit [88.30 (9)°] and is tilted slightly towards it. No π-π or C-H⋯π inter-actions are observed between neighbouring mol-ecules in the crystal structure because of steric hindrance induced by the three methyl groups.

| S-EPMC2962028 | biostudies-literature

5-Bromo-2,4,6-trimethyl-3-phenyl-sulfinyl-1-benzofuran.

Project description:The title compound, C(17)H(15)BrO(2)S, which was synthesized by the oxidation of 5-bromo-2,4,6-trimethyl-3-phenyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid, features a trigonally-coordinated S atom. The phenyl ring is approximately perpendicular to the plane of the benzofuran fragment [dihedral angle 75.11?(7)°]. The crystal structure is stabilized by non-classical C-H?O and Br?Br inter-actions [3.7169?(6)?Å].

| S-EPMC2960548 | biostudies-literature

5-Bromo-2,4,6-trimethyl-3-methyl-sulfinyl-1-benzofuran.

Project description:In the title compound, C(12)H(13)BrO(2)S, there are two symmetry-independent mol-ecules, A and B, in the asymmetric unit. The crystal studied was an inversion twin with a 0.70 (2):0.30 (2) domain ratio. The methyl-sulfinyl group in mol-ecule B is disordered over two positions with site-occupancy factors fixed at 0.6 and 0.4. The crystal structure is stabilized by C-H⋯O hydrogen bonds and inter-molecular C-H⋯π inter-actions. In addition, the crystal structure exhibits C-Br⋯π inter-actions, with C-Br⋯Cg1 = 3.646 (8) Å where Cg1 is the centroid of the furan ring.

| S-EPMC2959644 | biostudies-literature

3-(3-Bromo-phenyl-sulfin-yl)-5-cyclo-hexyl-2-methyl-1-benzo-furan.

Project description:In the title compound, C21H21BrO2S, the cyclo-hexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.178 (2) Å] of the benzo-furan ring system and the mean plane of the 3-bromo-phenyl ring is 86.52 (6)°. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π hydrogen bonds, and by a slipped π-π inter-action between the furan rings of neighbouring mol-ecules [centroid-centroid distance = 3.518 (3) Å, inter-planar distance = 3.471 (3) Å and slippage = 0.573 (3) Å], resulting in a three-dimensional network.

| S-EPMC3998404 | biostudies-literature

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