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Crystal structures of bis-[2-(di-phenyl-phosphino-thio-yl)phen-yl] ether and bis-{2-[diphen-yl(selanyl-idene)phosphan-yl]phen-yl} ether.

Janzen DE, Kooyman AM, Lange KA - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: The whole mol-ecule of compound (2) is generated by twofold symmetry, with the ether O atom located on the twofold axis.Both compounds have intra-molecular π-π inter-actions between terminal phenyl rings with centroid-centroid distances of 3.6214 (16) and 3.8027 (14) Å in (1) and (2), respectively.In the crystal of (1), short C-H⋯S hydrogen bonds link the mol-ecules, forming chains along [001], while in (2) there are no analogous C-H⋯Se inter-actions present.

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Affiliation: Department of Chemistry and Biochemistry, St Catherine University, St Paul, MN 55105, USA.

ABSTRACT
The title compounds, C36H28OP2S2, (1), and C36H28OP2Se2, (2), exhibit remarkably similar structures although they are not isomorphous. The whole mol-ecule of compound (2) is generated by twofold symmetry, with the ether O atom located on the twofold axis. Both compounds have intra-molecular π-π inter-actions between terminal phenyl rings with centroid-centroid distances of 3.6214 (16) and 3.8027 (14) Å in (1) and (2), respectively. In the crystal of (1), short C-H⋯S hydrogen bonds link the mol-ecules, forming chains along [001], while in (2) there are no analogous C-H⋯Se inter-actions present.

No MeSH data available.


Intra­molecular π–π inter­actions in (1) and (2).
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fig4: Intra­molecular π–π inter­actions in (1) and (2).

Mentions: The largest differences in the intra­molecular features of (1) and (2) can be found in the closest approach of a pair of terminal phenyl rings, each bonded to different phospho­rous atoms (Fig. 4 ▶). In the structure of (2), the angle between mean planes formed by atoms C1–C6 and the twofold axis-related atoms C1–C6 of the same mol­ecule is 0.98 (12)°, with a centroid–centroid distance of 3.8027 (14) Å. The analogous relationship in the structure of (1), involving phenyl rings C1–C6 and C31–C36, is a dihedral angle of 6.52 (13)° and a centroid–centroid distance of 3.6214 (16) Å. The result of these differences is that in (2) there is only one C⋯C intra­molecular contact between these phenyl rings shorter than 3.6 Å, while in (1) there are six unique contacts that meet this criteria. Although these intra­molecular C⋯C contacts are slightly longer than the van der Waals radii sum of 3.4 Å, the additional C⋯C close-contacts in (1) may contribute to stronger intra­molecular π–π inter­actions between these phenyl rings compared to (2). The dihedral angles between the mean planes formed by the ether-linked phenyl groups [(C13–C18 and C19–C24) 76.83 (11)° for (1); (C13–C18 and the symmetry-related C13–C18 ring) 84.53 (11)° for (2)] also show a significant difference in the twist around the ether linkage.


Crystal structures of bis-[2-(di-phenyl-phosphino-thio-yl)phen-yl] ether and bis-{2-[diphen-yl(selanyl-idene)phosphan-yl]phen-yl} ether.

Janzen DE, Kooyman AM, Lange KA - Acta Crystallogr Sect E Struct Rep Online (2014)

Intra­molecular π–π inter­actions in (1) and (2).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257402&req=5

fig4: Intra­molecular π–π inter­actions in (1) and (2).
Mentions: The largest differences in the intra­molecular features of (1) and (2) can be found in the closest approach of a pair of terminal phenyl rings, each bonded to different phospho­rous atoms (Fig. 4 ▶). In the structure of (2), the angle between mean planes formed by atoms C1–C6 and the twofold axis-related atoms C1–C6 of the same mol­ecule is 0.98 (12)°, with a centroid–centroid distance of 3.8027 (14) Å. The analogous relationship in the structure of (1), involving phenyl rings C1–C6 and C31–C36, is a dihedral angle of 6.52 (13)° and a centroid–centroid distance of 3.6214 (16) Å. The result of these differences is that in (2) there is only one C⋯C intra­molecular contact between these phenyl rings shorter than 3.6 Å, while in (1) there are six unique contacts that meet this criteria. Although these intra­molecular C⋯C contacts are slightly longer than the van der Waals radii sum of 3.4 Å, the additional C⋯C close-contacts in (1) may contribute to stronger intra­molecular π–π inter­actions between these phenyl rings compared to (2). The dihedral angles between the mean planes formed by the ether-linked phenyl groups [(C13–C18 and C19–C24) 76.83 (11)° for (1); (C13–C18 and the symmetry-related C13–C18 ring) 84.53 (11)° for (2)] also show a significant difference in the twist around the ether linkage.

Bottom Line: The whole mol-ecule of compound (2) is generated by twofold symmetry, with the ether O atom located on the twofold axis.Both compounds have intra-molecular π-π inter-actions between terminal phenyl rings with centroid-centroid distances of 3.6214 (16) and 3.8027 (14) Å in (1) and (2), respectively.In the crystal of (1), short C-H⋯S hydrogen bonds link the mol-ecules, forming chains along [001], while in (2) there are no analogous C-H⋯Se inter-actions present.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry and Biochemistry, St Catherine University, St Paul, MN 55105, USA.

ABSTRACT
The title compounds, C36H28OP2S2, (1), and C36H28OP2Se2, (2), exhibit remarkably similar structures although they are not isomorphous. The whole mol-ecule of compound (2) is generated by twofold symmetry, with the ether O atom located on the twofold axis. Both compounds have intra-molecular π-π inter-actions between terminal phenyl rings with centroid-centroid distances of 3.6214 (16) and 3.8027 (14) Å in (1) and (2), respectively. In the crystal of (1), short C-H⋯S hydrogen bonds link the mol-ecules, forming chains along [001], while in (2) there are no analogous C-H⋯Se inter-actions present.

No MeSH data available.