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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

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ABSTRACT

77: The title compounds, C23H16S, (I), and C26H16S, (II), are benzo­thio­phene derivatives in which the benzo­thio­phene 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 benzo­thio­phene 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-methyl­benzene 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, mol­ecules are linked by C—H⋯π inter­actions, leading to the formation of slabs parallel to (001) in (I) and to zigzag chains along [001] in (II). There are also offset π–π inter­actions 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., 9053–9071].

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The crystal packing of compound (I). The C—H⋯π inter­actions are shown as dashed lines (see Table 1 ▸ for details). H atoms not involved in these inter­actions have been omitted for clarity.
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fig3: The crystal packing of compound (I). The C—H⋯π inter­actions are shown as dashed lines (see Table 1 ▸ for details). H atoms not involved in these inter­actions have been omitted for clarity.

Mentions: In the crystals of both compounds, mol­ecules are linked by C—H⋯π inter­actions (see Tables 1 ▸ and 2 ▸), leading to the formation of slabs parallel to (001) in (I), and to zigzag chains along [001] in (II); as illustrated in Figs. 3 ▸, 4 ▸ and 5 ▸. There are also offset π–π inter­actions present within the slabs in (I) [Cg1⋯Cg3i = 3.629 (1) Å, inter­planar distance = 3.602 (1) Å, slippage = 0.49 Å; Cg2⋯Cg4ii = 3.983 (1), inter­planar distance = 3.473 (1), slippage 1.79 Å; Cg1, Cg2, Cg3 and Cg4 are the centroids of rings S1/C3/C4/C9/C10, C1–C3/C10–C12, C1/C12–C16 and C4–C9, respectively; symmetry codes: (i) x + 1, y, z; (ii) x − 1, y, z]. In the crystal of (II), offset π–π inter­actions link the chains, forming sheets parallel to (010) [Cg2⋯Cg4iii = 3.711 (2) Å, inter­planar distance = 3.479 (1) Å, slippage = 1.21 Å; Cg3⋯Cg4iii = 3.741 (2) Å, inter­planar distance = 3.443 (1) Å, slippage = 1.22 Å; Cg2, Cg3 and Cg4 are the centroids of rings C1–C3/C10–C12, C1/C12–C16 and C4–C9, respectively; symmetry code: (iii) −x + 1, −y + 1, −z + 1].


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
The crystal packing of compound (I). The C—H⋯π inter­actions are shown as dashed lines (see Table 1 ▸ for details). H atoms not involved in these inter­actions have been omitted for clarity.
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Related In: Results  -  Collection

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getmorefigures.php?uid=PMC5120714&req=5

fig3: The crystal packing of compound (I). The C—H⋯π inter­actions are shown as dashed lines (see Table 1 ▸ for details). H atoms not involved in these inter­actions have been omitted for clarity.
Mentions: In the crystals of both compounds, mol­ecules are linked by C—H⋯π inter­actions (see Tables 1 ▸ and 2 ▸), leading to the formation of slabs parallel to (001) in (I), and to zigzag chains along [001] in (II); as illustrated in Figs. 3 ▸, 4 ▸ and 5 ▸. There are also offset π–π inter­actions present within the slabs in (I) [Cg1⋯Cg3i = 3.629 (1) Å, inter­planar distance = 3.602 (1) Å, slippage = 0.49 Å; Cg2⋯Cg4ii = 3.983 (1), inter­planar distance = 3.473 (1), slippage 1.79 Å; Cg1, Cg2, Cg3 and Cg4 are the centroids of rings S1/C3/C4/C9/C10, C1–C3/C10–C12, C1/C12–C16 and C4–C9, respectively; symmetry codes: (i) x + 1, y, z; (ii) x − 1, y, z]. In the crystal of (II), offset π–π inter­actions link the chains, forming sheets parallel to (010) [Cg2⋯Cg4iii = 3.711 (2) Å, inter­planar distance = 3.479 (1) Å, slippage = 1.21 Å; Cg3⋯Cg4iii = 3.741 (2) Å, inter­planar distance = 3.443 (1) Å, slippage = 1.22 Å; Cg2, Cg3 and Cg4 are the centroids of rings C1–C3/C10–C12, C1/C12–C16 and C4–C9, respectively; symmetry code: (iii) −x + 1, −y + 1, −z + 1].

View Article: PubMed Central - HTML - PubMed

ABSTRACT

77: The title compounds, C23H16S, (I), and C26H16S, (II), are benzo­thio­phene derivatives in which the benzo­thio­phene 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 benzo­thio­phene 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-methyl­benzene 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, mol­ecules are linked by C—H⋯π inter­actions, leading to the formation of slabs parallel to (001) in (I) and to zigzag chains along [001] in (II). There are also offset π–π inter­actions 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., 9053–9071].

No MeSH data available.


Related in: MedlinePlus