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Crystal structure of 4'-bromo-2,3,5,6-tetra-fluoro-biphenyl-4-carbo-nitrile.

ABSTRACT: The title compound, C13H4BrF4N, synthesized from 1,4'-bromo-iodo-benzene and 4-bromo-2,3,5,6-tetra-fluoro-benzo-nitrile in a coupling reaction was found to crystallize in the ortho-rhom-bic space group P212121. The two phenyl rings are rotated with respect to each other by 40.6?(6)°. The mol-ecules inter-act via aryl-perfluoroaryl stacking [3.796?(2) and 3.773?(2)?Å], resulting in inter-molecular chains along the a-axis direction. C-H?F contacts of about 2.45?Å connect these chains. In contrast to the structure of the parent compound 4'-bromo-biphenyl-4-carbo-nitrile, CN?Br contacts that could have given rise to a linear arrangement of the biphenyl mol-ecules desirable for non-linear optical (NLO) materials are not observed in the packing. Instead, several Br?F [3.2405?(17) and 3.2777?(18)?Å] and F?F [2.894?(2)?Å] contacts of side-on type II form an inter-molecular network of zigzag chains. The crystal studied was refined as an inversion twin.

SUBMITTER: Heckel R

PROVIDER: S-EPMC4420037 | biostudies-literature | 2015 May

REPOSITORIES: biostudies-literature

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Crystal structure of 4'-bromo-2,3,5,6-tetra-fluoro-biphenyl-4-carbo-nitrile.

Heckel Ricarda R Hulliger Jürg J Schwarzer Anke A Weber Edwin E

Acta crystallographica. Section E, Crystallographic communications 20150425 Pt 5

The title compound, C13H4BrF4N, synthesized from 1,4'-bromo-iodo-benzene and 4-bromo-2,3,5,6-tetra-fluoro-benzo-nitrile in a coupling reaction was found to crystallize in the ortho-rhom-bic space group P212121. The two phenyl rings are rotated with respect to each other by 40.6 (6)°. The mol-ecules inter-act via aryl-perfluoroaryl stacking [3.796 (2) and 3.773 (2) Å], resulting in inter-molecular chains along the a-axis direction. C-H⋯F contacts of about 2.45 Å connect these chains. In contrast ...[more]

PMID: 25995941

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Project description:Reaction of FeCl2·4H2O with KSCN and 3-cyano-pyridine (pyridine-3-carbo-nitrile) in ethanol accidentally leads to the formation of single crystals of Fe(NCS)(Cl)(3-cyano-pyridine)4 or [FeCl(NCS)(C6H4N2)4]. The asymmetric unit of this compound consists of one FeII cation, one chloride and one thio-cyanate anion that are located on a fourfold rotation axis as well as of one 3-cyano-pyridine coligand in a general position. The FeII cations are sixfold coordinated by one chloride anion and one terminally N-bonding thio-cyanate anion in trans-positions and four 3-cyano-pyridine coligands that coordinate via the pyridine N atom to the FeII cations. The complexes are arranged in columns with the chloride anions, with the thio-cyanate anions always oriented in the same direction, which shows the non-centrosymmetry of this structure. No pronounced inter-molecular inter-actions are observed between the complexes. Initially, FeCl2 and KSCN were reacted in a 1:2 ratio, which lead to a sample that contains the title compound as the major phase together with a small amount of an unknown crystalline phase, as proven by powder X-ray diffraction (PXRD). If FeCl2 and KSCN is reacted in a 1:1 ratio, the title compound is obtained as a nearly pure phase. IR investigations reveal that the CN stretching vibration for the thio-cyanate anion is observed at 2074 cm-1, and that of the cyano group at 2238 cm-1, which also proves that the anionic ligands are only terminally bonded and that the cyano group is not involved in the metal coordination. Measurements with thermogravimetry and differential thermoanalysis reveal that the title compound decomposes at 169°C when heated at a rate of 4°C min-1 and that the 3-cyano-pyridine ligands are emitted in two separate poorly resolved steps. After the first step, an inter-mediate compound with the composition Fe(NCS)(Cl)(3-cyano-pyridine)2 of unknown structure is formed, for which the CN stretching vibration of the thio-cyanate anion is observed at 2025 cm-1, whereas the CN stretching vibration of the cyano group remain constant. This strongly indicates that the FeII cations are linked by μ-1,3-bridg-ing thio-cyanate anions into chains or layers.

Dataset Information

Crystal structure of 4'-bromo-2,3,5,6-tetra-fluoro-biphenyl-4-carbo-nitrile.

Publications

Crystal structure of 4'-bromo-2,3,5,6-tetra-fluoro-biphenyl-4-carbo-nitrile.

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