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1.  7-Bromo-1-(4-fluoro­phenyl­sulfon­yl)-2-methyl­naphtho­[2,1-b]furan 
In the title compound, C19H12BrFO3S, the 4-fluoro­phenyl ring makes a dihedral angle of 80.32 (5)° with the mean plane of the naphtho­furan fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O and C—H⋯π inter­actions. The crystal structure also exhibits aromatic π–π inter­actions between the central benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.564 (3) Å].
doi:10.1107/S160053681005436X
PMCID: PMC3051741  PMID: 21522972
2.  1-(4-Bromo­phenyl­sulfon­yl)-2-methyl­naphtho­[2,1-b]furan 
In the title compound, C19H13BrO3S, the 4-bromo­phenyl ring makes a dihedral angle of 64.11 (2)° with the mean plane [r.m.s. deviation = 0.01 (2) Å] of the naphtho­furan ring. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions. The crystal structure also exhibits slipped π–π inter­actions between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.559 (2), slippage = 1.036 (2) Å], and between the central naphtho­furan benzene ring and the furan ring of neighbouring mol­ecules [centroid–centroid distance = 3.655 (2), slippage = 1.136 (2) Å].
doi:10.1107/S160053681202939X
PMCID: PMC3414189  PMID: 22904796
3.  3-(4-Fluoro­phenyl­sulfon­yl)-2-methyl­naphtho­[1,2-b]furan 
In the title compound, C19H13FO3S, the 4-fluoro­phenyl ring makes a dihedral angle of 68.59 (5)° with the mean plane of the naphtho­furan fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O, C—H⋯F and C—H⋯π inter­actions. The crystal structure also exhibits aromatic π–π inter­actions between the central benzene and the outer benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.650 (3) Å].
doi:10.1107/S1600536810048361
PMCID: PMC3011502  PMID: 21589581
4.  1-(4-Bromo­phenyl­sulfin­yl)-2-methyl­naphtho­[2,1-b]furan 
In the title compound, C19H13BrO2S, the 4-bromo­phenyl ring makes a dihedral angle of 83.75 (4)° with the mean plane of the naphtho­furan fragment [r.m.s. deviation = 0.024 (2) Å]. In the crystal, mol­ecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers. These dimers are connected by weak π–π inter­actions between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.483 (2) Å, inter­planar distance = 3.416 (2) Å and slippage = 0.680 (2) Å].
doi:10.1107/S1600536812012603
PMCID: PMC3344175  PMID: 22606178
5.  3-(4-Chloro­phenyl­sulfon­yl)-2-methyl­naphtho[1,2-b]furan 
The title compound, C19H13ClO3S, was prepared by the oxidation of 3-(4-chloro­phenyl­sulfan­yl)-2-methyl­naphtho[1,2-b]furan with 3-chloro­peroxy­benzoic acid. The 4-chloro­phenyl ring makes a dihedral angle of 68.59 (5)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.635 (3) Å], and by C—H⋯π inter­actions between a methyl H atom and the furan ring of an adjacent mol­ecule. In addition, the crystal structure exhibits inter­molecular C—H⋯O inter­actions.
doi:10.1107/S1600536808009215
PMCID: PMC2961290  PMID: 21202325
6.  5-Bromo-3-(4-fluoro­phenyl­sulfon­yl)-2,7-dimethyl-1-benzofuran 
In the title compound, C16H12BrFO3S, the 4-fluoro­phenyl ring makes a dihedral angle of 72.35 (5)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked into [010] chains via two different inversion-generated pairs of C—H⋯O hydrogen bonds. The crystal structure also exhibits slipped π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.667 (2) Å and slippage = 1.341 (2) Å], and between the benzene and the furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.759 (2) Å and slippage = 0.757 (2) Å].
doi:10.1107/S1600536812043607
PMCID: PMC3515296  PMID: 23284516
7.  7-Bromo-2-(4-fluoro­phen­yl)-1-(methyl­sulfin­yl)naphtho[2,1-b]furan 
In the title compound, C19H12BrFO2S, the O atom and the methyl group of the methyl­sulfinyl substituent lie on opposite sides of the plane through the naphthofuran fragment. The 4-fluoro­phenyl ring is rotated out of the naphthofuran plane, making a dihedral angle of 41.65 (7)°. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O and C—H⋯π inter­actions, 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).
doi:10.1107/S1600536810011645
PMCID: PMC2979164  PMID: 21579076
8.  2-Methyl-1-(4-methyl­phenyl­sulfinyl)naphtho­[2,1-b]furan 
In the title compound, C20H16O2S, the 4-methyl­phenyl ring makes a dihedral angle of 82.60 (4)° with the mean plane [r.m.s. deviation = 0.007 (1) Å] of the naphtho­furan fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds, and by a slipped π–π inter­action between the central naphtho­furan benzene rings of neighbouring mol­ecules [centroid-to-centroid distance = 3.671 (2) Å, inter­planar distance = 3.349 (2) Å and slippage = 1.503 (2)°].
doi:10.1107/S1600536812003121
PMCID: PMC3275285  PMID: 22347141
9.  2-(4-Fluoro­phen­yl)-1-(phenyl­sulfin­yl)­naphtho­[2,1-b]furan 
In the title compound, C24H15FO2S, the 4-fluoro­phenyl ring makes a dihedral angle of 19.43 (4)° with the mean plane of the naphtho­furan fragment. The dihedral angle between the phenyl ring and the mean plane of the naphtho­furan fragment is 85.83 (4)°. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536811034155
PMCID: PMC3200676  PMID: 22059034
10.  7-Bromo-2-methyl-1-(phenyl­sulfon­yl)naphtho[2,1-b]furan 
The title compound, C19H13BrO3S, was prepared by the oxidation of 7-bromo-2-methyl-1-(phenyl­sulfan­yl)naph­tho[2,1-b]furan with 3-chloro­peroxy­benzoic 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 π–π stacking inter­actions between the brominated benzene ring and the central benzene ring of the naphthofuran system of neighbouring mol­ecules; the centroid–centroid distances within the stack are 3.889 (3) and 3.981 (3) Å. In addition, the stacked mol­ecules exhibit C—H⋯π, inter- and intra­molecular C—H⋯O inter­actions.
doi:10.1107/S160053680801177X
PMCID: PMC2961282  PMID: 21202425
11.  5-Fluoro-3-(3-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzofuran 
In the title compound, C15H10F2O3S, the 3-fluoro­phenyl ring makes a dihedral angle of 79.51 (6)° with the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯F and C—H⋯O hydrogen bonds. The crystal structure also exhibits slipped π–π inter­actions between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid distances = 3.563 (3) and 3.820 (3) Å and slippages of 0.358 (3)and 1.551 (3) Å]. In the 3-fluoro­phenyl ring, the F atom is disordered over two positions with site-occupancy factors of 0.887 (3) and 0.113 (3).
doi:10.1107/S1600536812031972
PMCID: PMC3414932  PMID: 22904919
12.  7-Bromo-2-methyl-1-tosyl­naphtho[2,1-b]furan 
The title compound, C20H15BrO3S, was prepared by the oxidation of 7-bromo-2-methyl-1-(4-tolyl­sulfan­yl)naph­tho[2,1-b]furan with 3-chloro­peroxy­benzoic acid. The 4-tolyl ring makes a dihedral angle of 70.96 (6)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by aromatic π–π stacking inter­actions, with centroid–centroid distances of 3.672 (3) and 3.858 (3) Å between the central benzene and furan rings, and between the brominated benzene and central benzene rings of the naphthofuran system of neighbouring mol­ecules, respectively. In addition, the stacked mol­ecules exhibit C—H⋯π and inter- and intra­molecular C—H⋯O inter­actions.
doi:10.1107/S1600536808015286
PMCID: PMC2961428  PMID: 21202666
13.  3-(3-Fluoro­phenyl­sulfon­yl)-2,5,7-trimethyl-1-benzofuran 
In the title compound, C17H15FO3S, the 3-fluoro­phenyl ring makes a dihedral angle of 73.39 (4)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds. The crystal structure also exhibits a slipped π–π inter­action between the furan and benzene rings of neighboring mol­ecules [centroid–centroid distance = 3.743 (2) Å, inter­planar distance = 3.543 (2) Å and slippage = 1.207 (2) Å].
doi:10.1107/S1600536811048525
PMCID: PMC3239004  PMID: 22199853
14.  3-(4-Fluoro­phenyl­sulfon­yl)-5-iodo-2,7-dimethyl-1-benzofuran 
In the title compound, C16H12FIO3S, the 4-fluoro­phenyl ring makes a dihedral angle of 72.31 (6)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules 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⋯π [3.901 (3) Å] inter­action and a slipped π–π inter­action between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.845 (3), inter­planar distance = 3.555 (3) and slippage = 1.465 (3) Å].
doi:10.1107/S1600536811052792
PMCID: PMC3254446  PMID: 22259594
15.  5-Bromo-2-(4-fluoro­phen­yl)-3-phenyl­sulfinyl-1-benzofuran 
In the title compound, C20H12BrFO2S, the 4-fluoro­phenyl ring makes a dihedral angle of 2.63 (6)° with the mean plane of the benzofuran fragment. The dihedral angle between the phenyl ring and the mean plane of the benzofuran fragment is 84.60 (6)°. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds, and slipped π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.719 (3) Å, inter­planar distance = 3.000 (3) Å and slippage = 1.520 (3) Å].
doi:10.1107/S1600536811032387
PMCID: PMC3200819  PMID: 22064889
16.  5-Bromo-3-(4-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzofuran 
In the title compound, C15H10BrFO3S, the 4-fluoro­phenyl ring makes a dihedral angle of 76.51 (6)° with the plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak non-classical inter­molecular C—H⋯O hydrogen bonds and an aromatic π–π inter­action between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.540 (3) Å].
doi:10.1107/S1600536810027741
PMCID: PMC3007450  PMID: 21588356
17.  2-Methyl-1-(phenyl­sulfon­yl)naphtho[2,1-b]furan 
The title compound, C19H14O3S, was prepared by the oxidation of 2-methyl-1-(phenyl­sulfan­yl)naphtho[2,1-b]furan with 3-chloro­peroxy­benzoic acid. The phenyl ring makes a dihedral angle of 87.13 (4)° with the plane of the naphthofuran fragment. The crystal structure is stabilized by π–π inter­actions between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.850 (2) Å] and weak C—H⋯π inter­actions. In addition, there are also intra­molecular C—H⋯O inter­actions.
doi:10.1107/S1600536808007046
PMCID: PMC2961025  PMID: 21202117
18.  2-Methyl-1-(3-methyl­phenyl­sulfon­yl)naphtho­[2,1-b]furan 
In the title compound, C20H16O3S, the dihedral angle between the mean planes of the naphtho­furan and 3-methyl­phenyl fragments is 88.56 (2)°. In the crystal, mol­ecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers. These dimers are linked by π–π inter­actions between the furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.701 (2) Å] into supra­molecular chains running along the a-axis direction.
doi:10.1107/S1600536814005157
PMCID: PMC3998563  PMID: 24826129
19.  7-Bromo-2-(4-methyl­phen­yl)-1-(methyl­sulfin­yl)naphtho­[2,1-b]furan 
In the title compound, C20H15BrO2S, the dihedral angle between the mean plane [r.m.s. deviation = 0.030 (2) Å] of the naphtho­furan ring system and the 4-methyl­phenyl ring is 38.49 (9)°. In the crystal, mol­ecules are linked by C—H⋯π and C—Br⋯π [3.871 (2) Å] inter­actions into stacks along the b-axis direction. These stacks are further linked by weak C—H⋯O hydrogen bonds, forming a three-dimensional network.
doi:10.1107/S1600536813016978
PMCID: PMC3770411  PMID: 24046696
20.  5-Bromo-3-(3-fluoro­phenyl­sulfin­yl)-2-methyl-1-benzofuran 
In the title compound, C15H10BrFO2S, the 3-fluoro­phenyl ring makes a dihedral angle of 85.0 (1)° with the mean plane [r.m.s. deviation = 0.008 (2) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds and a Br⋯O contact [3.200 (3) Å]. The crystal structure also exhibits slipped π–π inter­actions between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.619 (4) Å and slippage of 1.389 (4) Å]. In the 3-fluoro­phenyl ring, the F atom is disordered over two positions with site-occupancy factors of 0.583 (5) and 0.417 (5).
doi:10.1107/S1600536812032394
PMCID: PMC3414946  PMID: 22904933
21.  5-Cyclo­hexyl-3-(2-fluoro­phenyl­sulfon­yl)-2-methyl-1-benzo­furan 
In the title compound, C21H21FO3S, the cyclo­hexyl ring adopts a chair conformation. The dihedral angle between the mean planes of the benzo­furan ring system and the fluoro­phenyl ring is 87.61 (3)°. In the crystal, mol­ecules related by inversion are linked into dimers via pairs of C—H⋯π inter­actions. These dimers are further linked by π–π inter­actions between the furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.407 (2) Å and between the 2-fluoro­phenyl rings of neighbouring mol­ecules [centroid–centroid distance = 3.742 (2) Å], resulting in a three-dimensional supra­molecular network.
doi:10.1107/S1600536814005960
PMCID: PMC3998567  PMID: 24826165
22.  7-Bromo-2-phenyl-1-(phenyl­sulfin­yl)naphtho[2,1-b]furan benzene hemisolvate 
The title compound, C24H15BrO2S·0.5C6H6, crystallizes as a benzene hemisolvate. The O atom and the phenyl group of the phenyl­sulfinyl 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 π–π inter­actions between the central benzene ring and the furan ring of the neighbouring naphthofuran systems [centroid–centroid distance = 3.611 (3) Å], and by inter­molecular C—H⋯π inter­actions between the benzene H atom of the phenyl­sulfinyl substituent and the 2-phenyl ring of an adjacent mol­ecule. In addition, the crystal structure exhibits a weak non-classical inter­molecular C—H⋯O hydrogen bond.
doi:10.1107/S1600536809025860
PMCID: PMC2977353  PMID: 21583515
23.  2-(4-Bromo­phen­yl)-1-(phenyl­sulfin­yl)naphtho[2,1-b]furan 
In the title compound, C24H15BrO2S, the sulfinyl O atom and the phenyl group of the phenyl­sulfinyl 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-bromo­phenyl ring is rotated out of the naphthofuran plane by a dihedral angle of 31.12 (4)°. In the crystal structure, non-classical inter­molecular C—H⋯O and C—H⋯Br hydrogen bonds are observed. The crystal structure also exhibits aromatic π–π inter­actions between the furan ring and the central benzene ring of the adjacent naphthofuran system [centroid–centroid distance = 3.768 (3) Å]. In addition, inter­molecular C—Br⋯π inter­actions [3.866 (2) Å] between the Br atom and the phenyl ring of the phenyl­sulfinyl substituent are present.
doi:10.1107/S1600536809029250
PMCID: PMC2977400  PMID: 21583685
24.  7-Bromo-1-(4-chloro­phenyl­sulfan­yl)-2-phenyl­naphtho[2,1-b]furan 
In the title compound, C24H14BrClOS, the S-bound 4-chloro­phenyl 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 π–π inter­actions 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, inter­molecular C—Cl⋯π inter­actions [3.505 (2) Å] between the Cl atom and the 2-phenyl ring are present.
doi:10.1107/S1600536809052945
PMCID: PMC2980269  PMID: 21580059
25.  3-(4-Bromo­phenyl­sulfin­yl)-5-chloro-2-methyl-1-benzofuran 
In the title compound, C15H10BrClO2S, the 4-bromo­phenyl ring makes a dihedral angle of 86.85 (6)° with the mean plane [mean deviation = 0.009 (2) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by slipped π–π inter­actions between the benzene and the furan rings of adjacent mol­ecules [centroid–centroid distance = 3.884 (2), inter­planar distance = 3.369 (2) and slippage = 1.945 (2) Å], and between the 4-bromo­phenyl rings of adjacent mol­ecules [centroid–centroid distance = 3.882 (2), inter­planar distance = 3.552 (2) and slippage = 1.566 (2) Å]. A Br⋯Br [3.6446 (4) Å] halogen inter­action is also observed.
doi:10.1107/S1600536812025846
PMCID: PMC3393896  PMID: 22798761

Results 1-25 (94558)