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6-Phenyl-benzo[d]naphtho-[2,3-b]thio-phene.

ABSTRACT: In the title compound, C22H14S, the r.m.s. deviation from the mean plane of the four-fused-ring naphtho-thio-phene unit is 0.056?Å. The dihedral angle between the naphtho-thio-phene plane and the pendant phenyl ring is 67.24?(6)°. In the crystal, weak C-H?? and ?-? stacking [minimum centroid-centroid separation = 3.7466?(10)?Å] inter-actions are observed, which together lead to (010) sheets.

SUBMITTER: Silambarasan V

PROVIDER: S-EPMC3588245 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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6-Phenyl-benzo[d]naphtho-[2,3-b]thio-phene.

Silambarasan V V Srinivasan T T Sivasakthikumaran R R Mohanakrishnan A K AK Velmurugan D D

Acta crystallographica. Section E, Structure reports online 20121208 Pt 1

In the title compound, C22H14S, the r.m.s. deviation from the mean plane of the four-fused-ring naphtho-thio-phene unit is 0.056 Å. The dihedral angle between the naphtho-thio-phene plane and the pendant phenyl ring is 67.24 (6)°. In the crystal, weak C-H⋯π and π-π stacking [minimum centroid-centroid separation = 3.7466 (10) Å] inter-actions are observed, which together lead to (010) sheets. ...[more]

PMID: 23476423

Similar Datasets

Crystal structure of 6-(p-tol-yl)benzo[b]naphtho[2,3-d]thio-phene and of an ortho-rhom-bic polymorph of 7-phenyl-anthra[2,3-b]benzo[d]thio-phene.

Project description:The title compounds, C23H16S, (I), and C26H16S, (II), are benzo-thio-phene derivatives in which the benzo-thio-phene moiety is fused with a naphthalene ring system in (I), and with an anthracene ring system in (II). In (I), the mean plane of the benzo-thio-phene ring system makes a dihedral angle of 2.28?(6)° with the naphthalene ring system, and a dihedral angle of 1.28?(6)° with the anthracene ring system in (II), showing that the fused units are essentially planar. In (I), the 4-methyl-benzene ring substituent makes a dihedral angle of 71.40?(9)° with the naphthalene ring system, while the phenyl ring substituent in (II) makes a dihedral angle of 67.08?(12)° with the anthracene ring system. In the crystals of both compounds, mol-ecules are linked by C-H?? inter-actions, leading to the formation of slabs parallel to (001) in (I) and to zigzag chains along [001] in (II). There are also offset ?-? inter-actions present within the slabs in (I). In the crystal of (II), they link the chains, forming sheets parallel to (010). The triclinic polymorph of compound (II) has been reported [Sivasakthikumaran et al., (2012 ?). J. Org. Chem.77, 9053-9071].

| S-EPMC5120714 | biostudies-literature

4-(4-Meth-oxy-phen-yl)naphtho-[2,3-b]thio-phene.

Project description:In the title compound, C(19)H(14)OS, the naphtho-thio-phene moiety is almost planar except for the S atom of the five-membered ring, which is situated 0.047 (6) Å out of the C(4) plane (with an r.m.s. deviation of fitted atoms = 0.0009 Å). The dihedral angle between the naphtho-thio-phene plane and the attached meth-oxy-phenyl ring is 67.6 (2)°. In the crystal, a C-H⋯π inter-action is observed between a meth-oxy-phenyl C-H group and the outer benzene ring of the naphtho-thio-phene moiety. The five-membered ring of the naphtho-thio-phene moiety is disordered, with the S and opposite non-fused C atom approximately exchanging positions, with a site-occupancy factors of 0.808 (3) and 0.187 (3).

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5-Methyl-phenanthro[2,3-b]thio-phene.

Project description:The title compound, C(17)H(12)S, which crystallises with two molecules in the asymmetric unit, features four fused rings forming an essentially planar mol-ecule, with maximum deviations from the mean plane of 0.078?(2) and 0.080?(2)?Å for C atoms of the thio-phene and phenanthrene groups in both the mol-ecules. The crystal packing features weak C-H?? inter-actions.

| S-EPMC3089194 | biostudies-literature

Thio-phene-2-carbaldehyde 2,4-dinitro-phenyl-hydrazone.

Project description:In the approximately planar molecule of the title compound, C(11)H(8)N(4)O(4)S, the dihedral angle between the thio-phene and benzene rings is 5.73 (10)°. In the crystal structure, bifurcated inter/intra-molecular N-H⋯(O,O) hydrogen bonds are present. The intermolecular links lead to inversion dimers containing an R(2) (2)(12) graph-set motif.

| S-EPMC2959885 | biostudies-literature

6-(4-Meth-oxy-phen-yl)naphtho[2,3-b][1]benzothio-phene.

Project description:The asymmetric unit of the title compound, C23H16OS, contains two independent mol-ecules with opposite orientations of the meth-oxy groups bonded to the benzene rings. The napthobenzothiophene group in the two molecules is separated by an average distance of 3.912 Å. In both mol-ecules, the napthobenzothio-phene unit is almost planar, with r.m.s deviations of 0.0522 and 0.0143 Å. The meth-oxy-phenyl ring makes dihedral angles of 67.0 (6)° and 70.4 (6)° with respect to the napthobenzothio-phene ring system in the two mol-ecules. The crystal packing features C-H⋯S, π-π [centroid-centroid distances = 3.666 (10) and 3.658 (10) Å] and C-H⋯π inter-actions, forming a sheet running along the b-axis direction.

| S-EPMC3588996 | biostudies-literature

2-Amino-4,5,6,7-tetra-hydro-benzo[b]thio-phene-3-carbonitrile.

Project description:The title compound, C(9)H(10)N(2)S, was synthesized according to Gewald procedures by the reaction of cyclo-hexa-none with malonitrile and sulfur in the presence morpholine. The cyclo-hexane ring adopts a half-chair conformation and the thio-phene ring is essentially planar (r.m.s. deviation = 0.05 Å). The crystal packing is stabilized by two inter-molecular N-H⋯N hydrogen bonds, which link the mol-ecules into centrosymmetric rings with graph-set motif R(2) (2)(12).

| S-EPMC3238832 | biostudies-literature

3,4-Di-methyl-thieno[2,3-b]thio-phene-2,5-dicarbo-nitrile.

Project description:The asymmetric unit of the title compound, C10H6N2S2, contains two crystallographically independent but conformationally similar mol-ecules. The fused thio-phene ring cores are almost planar [maximum deviation = 0.027?(3)?Å] with the thio-phene rings forming dihedral angles of 0.5?(4)° in one mol-ecule and 1.91?(4)° in the other. The crystal packing is stabilized only by van der Waals inter-actions.

| S-EPMC3793767 | biostudies-literature

Diethyl 3,4-dimethyl-thieno[2,3-b]thio-phene-2,5-dicarboxyl-ate.

Project description:In the title compound, C14H16O4S2, the thieno[2,3-b]thio-phene ring systems are planar [maximum deviation = 0.008 (2) Å]. The mol-ecular conformation is stabilized by intra-molecular C-H⋯O hydrogen bonds, while the crystal packing is stabilized by C-H⋯O, C-H⋯π and π-π stacking [centroid-centroid distance = 3.6605 (14) Å] inter-actions, which lead to supra-molecular layers in the ab plane.

| S-EPMC3588935 | biostudies-literature

2-(2-Nitro-anilino)-4,5,6,7-tetra-hydro-benzo[b]thio-phene-3-carbonitrile.

Project description:The title compound, C(15)H(13)N(3)O(2)S, was synthesized by the reaction of 2-amino-5,6,7,8-tetra-hydro-4H-cyclo-hepta-[b]thio-phene-3-carbonitrile and o-fluoro-nitro-benzene. The dihedral angle between the thio-phene and nitro-phenyl rings is 75.15 (2)°. In the crystal, inter-molecular N-H⋯N and C-H⋯O inter-actions lead to the formation of a supra-molecular chain extending along the c-axis direction.

| S-EPMC2983395 | biostudies-literature

3,3-Dimethyl-1,2,3,4,6,11-hexa-hydro-benzo[d]naphtho[2,3-b]furan-1,6,11-trione.

Project description:In the title compound, C(18)H(14)O(4), the cyclo-hexene ring adopts a sofa conformation. In the crystalline state, the mol-ecules are linked into a chain by weak inter-molecular C-H⋯O hydrogen bonds.

| S-EPMC2962159 | biostudies-literature

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