X-ray Structure Analysis Online
Online ISSN : 1883-3578
ISSN-L : 1883-3578
Part 9
Crystal Structure Refinement of 1,4,5,8-Tetrabromonaphthalene: A Twisted Chiral Naphthalene Induced by Steric Repulsion
Md Awlad HOSSAINKazunori HIRABAYASHITohru NISHINAGAToshio SHIMIZUKen-ichi SUGIURA
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Supplementary material

2020 Volume 36 Pages 35-37

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Abstract

The molecular structure of sterically crowded 1,4,5,8-tetrabromonaphthalene 1 was refined. The compound crystallized in a monoclinic system and was characterized as follows: P21/c, a = 9.470(3), b = 15.530(4), c = 7.340(2)Å, β = 92.147(9)°, Z = 4, V = 1078.7(5)Å3. The crystal structure was solved by direct methods and refined by full-matrix least-squares on F2 to final values of R1 = 0.0332 and wR2 = 0.0572. Because of the steric repulsion between the peri-bromines, 1 takes a twisted structure having a D2 point group, i.e., a chiral structure. Symmetry operation of this space group generates the corresponding enantiomer in the crystal. In marked contrast to the noticeably short intramolecular Br–Br contact of 3.209 Å (average), there is no short Br–Br contact intermolecularly.

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© 2020 by The Japan Society for Analytical Chemistry
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