2,2′′,3,3′′,4,4′′,5, 5′′-Octa-phenyl-1,1′: 4′,1′′-terphenyl and 2′,3′,5′,6′-tetra-fluoro-2,2′′,3, 3′′,4,4′′,5,5′′-octa-phenyl-1,1′: 4′,1′′-terphen-yl

Stephen M. Budy, Gary S. Nichol, Douglas A Loy

Research output: Contribution to journalArticle

Abstract

The title compounds, C66H46, (I), and C66H42F4, (II), are polyphenyl-ated aryl-enes synthesized by one-step Diels-Alder cyclo-addition reactions. In both structures, all mol-ecules lie on crystallographic inversion centers. In the case of (I), there are two half-mol-ecules present in the asymmetric unit, (IA) and (IB); the geometry of each half-mol-ecule differs principally in the magnitudes of the dihedral angles between mean planes fitted through the central aryl ring and the pendant phenyl rings. The crystal used was a non-merohedral twin, with a refined twin scale factor of 0.460 (8). The dihedral angle between the plane of the central tetra-fluorinated ring and the adjacent tetra-phenyl-ated ring in (II) is 83.87 (4)°, significantly greater than the dihedral angles of 49.89 (12) and 54.38 (10)° found in the two half-mol-ecules in (IA) and (IB), respectively, and attributed to inter-molecular C - H⋯F hydrogen bonding in (II). Inter-molecular C - H⋯π bonding is found in (I). Two inter-actions have the C - H bond oriented towards the centroid (Cg) of a butadiene fragment of a phenyl ring; both H⋯Cg distances are approximately 2.68 Å and the inter-actions connect adjacent mol-ecules into stacks in the c-axis direction. The composition of the stacks alternates, i.e. (IA)-(IB)-(IA)-(IB) etc. A third, weaker, C - H⋯π inter-action and a phen-yl-phenyl close contact connect each end of the long mol-ecular axes of (IB) with an adjacent mol-ecule of (IA) into chains which run perpendicular to the (140) and ( 40) planes. C - H⋯F inter-actions in (II) have the most profound influence on the mol-ecular and crystal structure, the main effect of which is the above-mentioned increase in the dihedral angle between the plane of the central tetra-fluorinated ring and the adjacent tetra-phenyl-ated ring. C - H⋯F inter-actions have refined H⋯F distances of 2.572 (15) and 2.642 (16) Å, with approximate C - H⋯F angles of 123 and 157°, respectively. These form a hydrogen-bonded ribbon structure which propagates in the b-axis direction.

Original languageEnglish (US)
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume68
Issue number1
DOIs
StatePublished - Jan 2012

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Dihedral angle
Hydrogen Bonding
Hydrogen
Addition reactions
Hydrogen bonds
Crystal structure
Crystals
Geometry
Direction compound
Chemical analysis
1,3-butadiene

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

@article{b7b309c1868d424ea3afdab13ae05e1a,
title = "2,2′′,3,3′′,4,4′′,5, 5′′-Octa-phenyl-1,1′: 4′,1′′-terphenyl and 2′,3′,5′,6′-tetra-fluoro-2,2′′,3, 3′′,4,4′′,5,5′′-octa-phenyl-1,1′: 4′,1′′-terphen-yl",
abstract = "The title compounds, C66H46, (I), and C66H42F4, (II), are polyphenyl-ated aryl-enes synthesized by one-step Diels-Alder cyclo-addition reactions. In both structures, all mol-ecules lie on crystallographic inversion centers. In the case of (I), there are two half-mol-ecules present in the asymmetric unit, (IA) and (IB); the geometry of each half-mol-ecule differs principally in the magnitudes of the dihedral angles between mean planes fitted through the central aryl ring and the pendant phenyl rings. The crystal used was a non-merohedral twin, with a refined twin scale factor of 0.460 (8). The dihedral angle between the plane of the central tetra-fluorinated ring and the adjacent tetra-phenyl-ated ring in (II) is 83.87 (4)°, significantly greater than the dihedral angles of 49.89 (12) and 54.38 (10)° found in the two half-mol-ecules in (IA) and (IB), respectively, and attributed to inter-molecular C - H⋯F hydrogen bonding in (II). Inter-molecular C - H⋯π bonding is found in (I). Two inter-actions have the C - H bond oriented towards the centroid (Cg) of a butadiene fragment of a phenyl ring; both H⋯Cg distances are approximately 2.68 {\AA} and the inter-actions connect adjacent mol-ecules into stacks in the c-axis direction. The composition of the stacks alternates, i.e. (IA)-(IB)-(IA)-(IB) etc. A third, weaker, C - H⋯π inter-action and a phen-yl-phenyl close contact connect each end of the long mol-ecular axes of (IB) with an adjacent mol-ecule of (IA) into chains which run perpendicular to the (140) and ( 40) planes. C - H⋯F inter-actions in (II) have the most profound influence on the mol-ecular and crystal structure, the main effect of which is the above-mentioned increase in the dihedral angle between the plane of the central tetra-fluorinated ring and the adjacent tetra-phenyl-ated ring. C - H⋯F inter-actions have refined H⋯F distances of 2.572 (15) and 2.642 (16) {\AA}, with approximate C - H⋯F angles of 123 and 157°, respectively. These form a hydrogen-bonded ribbon structure which propagates in the b-axis direction.",
author = "Budy, {Stephen M.} and Nichol, {Gary S.} and Loy, {Douglas A}",
year = "2012",
month = "1",
doi = "10.1107/S0108270111051900",
language = "English (US)",
volume = "68",
journal = "Acta Crystallographica Section C: Crystal Structure Communications",
issn = "0108-2701",
publisher = "International Union of Crystallography",
number = "1",

}

TY - JOUR

T1 - 2,2′′,3,3′′,4,4′′,5, 5′′-Octa-phenyl-1,1′

T2 - 4′,1′′-terphenyl and 2′,3′,5′,6′-tetra-fluoro-2,2′′,3, 3′′,4,4′′,5,5′′-octa-phenyl-1,1′: 4′,1′′-terphen-yl

AU - Budy, Stephen M.

AU - Nichol, Gary S.

AU - Loy, Douglas A

PY - 2012/1

Y1 - 2012/1

N2 - The title compounds, C66H46, (I), and C66H42F4, (II), are polyphenyl-ated aryl-enes synthesized by one-step Diels-Alder cyclo-addition reactions. In both structures, all mol-ecules lie on crystallographic inversion centers. In the case of (I), there are two half-mol-ecules present in the asymmetric unit, (IA) and (IB); the geometry of each half-mol-ecule differs principally in the magnitudes of the dihedral angles between mean planes fitted through the central aryl ring and the pendant phenyl rings. The crystal used was a non-merohedral twin, with a refined twin scale factor of 0.460 (8). The dihedral angle between the plane of the central tetra-fluorinated ring and the adjacent tetra-phenyl-ated ring in (II) is 83.87 (4)°, significantly greater than the dihedral angles of 49.89 (12) and 54.38 (10)° found in the two half-mol-ecules in (IA) and (IB), respectively, and attributed to inter-molecular C - H⋯F hydrogen bonding in (II). Inter-molecular C - H⋯π bonding is found in (I). Two inter-actions have the C - H bond oriented towards the centroid (Cg) of a butadiene fragment of a phenyl ring; both H⋯Cg distances are approximately 2.68 Å and the inter-actions connect adjacent mol-ecules into stacks in the c-axis direction. The composition of the stacks alternates, i.e. (IA)-(IB)-(IA)-(IB) etc. A third, weaker, C - H⋯π inter-action and a phen-yl-phenyl close contact connect each end of the long mol-ecular axes of (IB) with an adjacent mol-ecule of (IA) into chains which run perpendicular to the (140) and ( 40) planes. C - H⋯F inter-actions in (II) have the most profound influence on the mol-ecular and crystal structure, the main effect of which is the above-mentioned increase in the dihedral angle between the plane of the central tetra-fluorinated ring and the adjacent tetra-phenyl-ated ring. C - H⋯F inter-actions have refined H⋯F distances of 2.572 (15) and 2.642 (16) Å, with approximate C - H⋯F angles of 123 and 157°, respectively. These form a hydrogen-bonded ribbon structure which propagates in the b-axis direction.

AB - The title compounds, C66H46, (I), and C66H42F4, (II), are polyphenyl-ated aryl-enes synthesized by one-step Diels-Alder cyclo-addition reactions. In both structures, all mol-ecules lie on crystallographic inversion centers. In the case of (I), there are two half-mol-ecules present in the asymmetric unit, (IA) and (IB); the geometry of each half-mol-ecule differs principally in the magnitudes of the dihedral angles between mean planes fitted through the central aryl ring and the pendant phenyl rings. The crystal used was a non-merohedral twin, with a refined twin scale factor of 0.460 (8). The dihedral angle between the plane of the central tetra-fluorinated ring and the adjacent tetra-phenyl-ated ring in (II) is 83.87 (4)°, significantly greater than the dihedral angles of 49.89 (12) and 54.38 (10)° found in the two half-mol-ecules in (IA) and (IB), respectively, and attributed to inter-molecular C - H⋯F hydrogen bonding in (II). Inter-molecular C - H⋯π bonding is found in (I). Two inter-actions have the C - H bond oriented towards the centroid (Cg) of a butadiene fragment of a phenyl ring; both H⋯Cg distances are approximately 2.68 Å and the inter-actions connect adjacent mol-ecules into stacks in the c-axis direction. The composition of the stacks alternates, i.e. (IA)-(IB)-(IA)-(IB) etc. A third, weaker, C - H⋯π inter-action and a phen-yl-phenyl close contact connect each end of the long mol-ecular axes of (IB) with an adjacent mol-ecule of (IA) into chains which run perpendicular to the (140) and ( 40) planes. C - H⋯F inter-actions in (II) have the most profound influence on the mol-ecular and crystal structure, the main effect of which is the above-mentioned increase in the dihedral angle between the plane of the central tetra-fluorinated ring and the adjacent tetra-phenyl-ated ring. C - H⋯F inter-actions have refined H⋯F distances of 2.572 (15) and 2.642 (16) Å, with approximate C - H⋯F angles of 123 and 157°, respectively. These form a hydrogen-bonded ribbon structure which propagates in the b-axis direction.

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U2 - 10.1107/S0108270111051900

DO - 10.1107/S0108270111051900

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VL - 68

JO - Acta Crystallographica Section C: Crystal Structure Communications

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