Browse
Submit Data
Databases
API
Help

Dataset Information

24 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

2-(4-Bromo-phen-yl)-1-(phenyl-sulfin-yl)naphtho[2,1-b]furan.

ABSTRACT: In the title compound, C(24)H(15)BrO(2)S, the sulfinyl O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane through the naphthofuran fragment. The phenyl ring is nearly perpendicular to the plane of the tricyclic naphthofuran system [81.77?(6)°] and is tilted slightly towards it. The 4-bromo-phenyl ring is rotated out of the naphthofuran plane by a dihedral angle of 31.12?(4)°. In the crystal structure, non-classical inter-molecular C-H?O and C-H?Br hydrogen bonds are observed. The crystal structure also exhibits aromatic ?-? inter-actions between the furan ring and the central benzene ring of the adjacent naphthofuran system [centroid-centroid distance = 3.768?(3)?Å]. In addition, inter-molecular C-Br?? inter-actions [3.866?(2)?Å] between the Br atom and the phenyl ring of the phenyl-sulfinyl substituent are present.

SUBMITTER: Choi HD

PROVIDER: S-EPMC2977400 | biostudies-literature | 2009 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

2-(4-Bromo-phen-yl)-1-(phenyl-sulfin-yl)naphtho[2,1-b]furan.

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

Acta crystallographica. Section E, Structure reports online 20090729 Pt 8

In the title compound, C(24)H(15)BrO(2)S, the sulfinyl O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane through the naphthofuran fragment. The phenyl ring is nearly perpendicular to the plane of the tricyclic naphthofuran system [81.77 (6)°] and is tilted slightly towards it. The 4-bromo-phenyl ring is rotated out of the naphthofuran plane by a dihedral angle of 31.12 (4)°. In the crystal structure, non-classical inter-molecular C-H⋯O and C-H⋯Br h ...[more]

PMID: 21583685

Similar Datasets

1-(4-Bromo-phenyl-sulfin-yl)-2-methyl-naphtho-[2,1-b]furan.

Project description:In the title compound, C(19)H(13)BrO(2)S, the 4-bromo-phenyl ring makes a dihedral angle of 83.75?(4)° with the mean plane of the naphtho-furan fragment [r.m.s. deviation = 0.024?(2)?Å]. In the crystal, mol-ecules are linked via pairs of C-H?O hydrogen bonds, forming inversion dimers. These dimers are connected by weak ?-? inter-actions between the central naphtho-furan benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.483?(2)?Å, inter-planar distance = 3.416?(2)?Å and slippage = 0.680?(2)?Å].

| S-EPMC3344175 | biostudies-literature

7-Bromo-2-phenyl-1-(phenyl-sulfin-yl)naphtho[2,1-b]furan benzene hemisolvate.

Project description:The title compound, C(24)H(15)BrO(2)S·0.5C(6)H(6), crystallizes as a benzene hemisolvate. The O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the naphthofuran fragment, and the phenyl ring is almost perpendicular to the plane of the naphthofuran fragment [83.78?(8)°] and is tilted slightly towards it. The 2-phenyl ring is rotated out of the naphthofuran plane by a dihedral angle of 25.2?(1)°. The crystal structure is stabilized by aromatic ?-? inter-actions between the central benzene ring and the furan ring of the neighbouring naphthofuran systems [centroid-centroid distance = 3.611?(3)?Å], and by inter-molecular C-H?? inter-actions between the benzene H atom of the phenyl-sulfinyl substituent and the 2-phenyl ring of an adjacent mol-ecule. In addition, the crystal structure exhibits a weak non-classical inter-molecular C-H?O hydrogen bond.

| S-EPMC2977353 | biostudies-literature

2-(4-Fluoro-phen-yl)-1-(phenyl-sulfin-yl)-naphtho-[2,1-b]furan.

Project description:In the title compound, C(24)H(15)FO(2)S, the 4-fluoro-phenyl ring makes a dihedral angle of 19.43?(4)° with the mean plane of the naphtho-furan fragment. The dihedral angle between the phenyl ring and the mean plane of the naphtho-furan fragment is 85.83?(4)°. In the crystal, mol-ecules are linked by weak inter-molecular C-H?O hydrogen bonds.

| S-EPMC3200676 | biostudies-literature

2-Phenyl-1-(phenyl-sulfin-yl)naphtho[2,1-b]furan.

Project description:In the title compound, C(24)H(16)O(2)S, the O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the naphthofuran fragment; the phenyl ring is almost perpendicular to this plane [82.34?(5)°]. The 2-phenyl ring is rotated out of the naphthofuran plane making a dihedral angle of 48.21?(6)°. The crystal structure shows ?-? inter-actions between the central benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.516?(3)?Å], as well as non-classical C-H?O hydrogen bonds.

| S-EPMC2969545 | biostudies-literature

7-Bromo-2-(4-fluoro-phen-yl)-1-(methyl-sulfin-yl)naphtho[2,1-b]furan.

Project description:In the title compound, C(19)H(12)BrFO(2)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane through the naphthofuran fragment. The 4-fluoro-phenyl ring is rotated out of the naphthofuran plane, making a dihedral angle of 41.65?(7)°. In the crystal, mol-ecules are linked by weak inter-molecular C-H?O and C-H?? inter-actions, and a short Br?F contact [3.046?(2)?Å] occurs. The O atom of the sulfinyl group is disordered over two positions, with refined site-occupancy factors of 0.912?(4) and 0.088?(4).

| S-EPMC2979164 | biostudies-other

7-Bromo-2-(4-methyl-phen-yl)-1-(methyl-sulfin-yl)naphtho-[2,1-b]furan.

Project description:In the title compound, C20H15BrO2S, the dihedral angle between the mean plane [r.m.s. deviation = 0.030?(2)?Å] of the naphtho-furan ring system and the 4-methyl-phenyl ring is 38.49?(9)°. In the crystal, mol-ecules are linked by C-H?? and C-Br?? [3.871?(2)?Å] inter-actions into stacks along the b-axis direction. These stacks are further linked by weak C-H?O hydrogen bonds, forming a three-dimensional network.

| S-EPMC3770411 | biostudies-other

1-(4-Bromo-phenyl-sulfon-yl)-2-methyl-naphtho-[2,1-b]furan.

Project description:In the title compound, C(19)H(13)BrO(3)S, the 4-bromo-phenyl ring makes a dihedral angle of 64.11?(2)° with the mean plane [r.m.s. deviation = 0.01?(2)?Å] of the naphtho-furan ring. In the crystal, mol-ecules are linked by weak C-H?O and C-H?? inter-actions. The crystal structure also exhibits slipped ?-? inter-actions between the central naphtho-furan benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.559?(2), slippage = 1.036?(2)?Å], and between the central naphtho-furan benzene ring and the furan ring of neighbouring mol-ecules [centroid-centroid distance = 3.655?(2), slippage = 1.136?(2)?Å].

| S-EPMC3414189 | biostudies-literature

7-Bromo-2-methyl-1-(phenyl-sulfon-yl)naphtho[2,1-b]furan.

Project description:The title compound, C(19)H(13)BrO(3)S, was prepared by the oxidation of 7-bromo-2-methyl-1-(phenyl-sulfan-yl)naph-tho[2,1-b]furan with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 80.4?(2)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by aromatic ?-? stacking inter-actions between the brominated benzene ring and the central benzene ring of the naphthofuran system of neighbouring mol-ecules; the centroid-centroid distances within the stack are 3.889?(3) and 3.981?(3)?Å. In addition, the stacked mol-ecules exhibit C-H??, inter- and intra-molecular C-H?O inter-actions.

| S-EPMC2961282 | biostudies-literature

7-Bromo-1-(4-chloro-phenyl-sulfan-yl)-2-phenyl-naphtho[2,1-b]furan.

Project description:In the title compound, C(24)H(14)BrClOS, the S-bound 4-chloro-phenyl ring is nearly perpendicular to the plane of the naphthofuran fragment [dihedral angle = 83.34?(3)°] and the phenyl ring in the 2-position is rotated out of the naphthofuran plane by a dihedral angle of 15.23?(5)°. The crystal structure is stabilized by aromatic ?-? inter-actions between the furan and the central benzene rings of the neighbouring naphthofuran fragments, and between the outer benzene rings of the neighbouring naphthofuran fragments; the centroid-centroid distances within the stack are 3.879?(2) and 3.857?(2)?Å. In addition, inter-molecular C-Cl?? inter-actions [3.505?(2)?Å] between the Cl atom and the 2-phenyl ring are present.

| S-EPMC2980269 | biostudies-literature

2-Phenyl-3-(phenyl-sulfin-yl)naphtho[1,2-b]furan.

| S-EPMC2969341 | biostudies-literature