Acta Crystallographica Section C

Crystal Structure Communications

Volume 68, Part 1 (January 2012)


organic compounds



eg3079 scheme

Acta Cryst. (2012). C68, o23-o27    [ doi:10.1107/S0108270111051900 ]

2,2'',3,3'',4,4'',5,5''-Octa­phenyl-1,1':4',1''-terphenyl and 2',3',5',6'-tetra­fluoro-2,2'',3,3'',4,4'',5,5''-octa­phenyl-1,1':4',1''-terphen­yl

S. M. Budy, G. S. Nichol and D. A. Loy

Abstract: The title compounds, C66H46, (I), and C66H42F4, (II), are polyphenyl­ated aryl­enes synthesized by one-step Diels-Alder cyclo­addition reactions. In both structures, all mol­ecules lie on crystallographic inversion centers. In the case of (I), there are two half-mol­ecules present in the asymmetric unit, (IA) and (IB); the geometry of each half-mol­ecule 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 tetra­fluorinated ring and the adjacent tetra­phenyl­ated 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-mol­ecules in (IA) and (IB), respectively, and attributed to inter­molecular C-H...F hydrogen bonding in (II). Inter­molecular C-H...[pi] bonding is found in (I). Two inter­actions 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 inter­actions connect adjacent mol­ecules 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...[pi] inter­action and a phen­yl-phenyl close contact connect each end of the long mol­ecular axes of (IB) with an adjacent mol­ecule of (IA) into chains which run perpendicular to the (140) and (\overline{1}40) planes. C-H...F inter­actions in (II) have the most profound influence on the mol­ecular and crystal structure, the main effect of which is the above-mentioned increase in the dihedral angle between the plane of the central tetra­fluorinated ring and the adjacent tetra­phenyl­ated ring. C-H...F inter­actions 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.

Formula: C66H46 and C66H42F4


hkldisplay filedownload file

Structure factor file (CIF format) (352.3 kbytes)
[ doi:10.1107/S0108270111051900/eg3079Isup2.hkl ]
Contains datablock I


hkldisplay filedownload file

Structure factor file (CIF format) (333.2 kbytes)
[ doi:10.1107/S0108270111051900/eg3079IIsup3.hkl ]
Contains datablock II


Notes:

To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

 bibliographic record in  format

  Find reference:   Volume   Page   
  Search:     From   to      Advanced search

Copyright © International Union of Crystallography
IUCr Webmaster