Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 3 (March 2013)

organic compounds

Acta Cryst. (2013). C69, 247-250    [ doi:10.1107/S010827011300231X ]

A tetra­bromo-1,4-ethano­naphthalene and related dibromo-1,4-etheno­naphthalene

R. T. Boeré and C. O. Bender

Abstract: (1RS,3RS,4RS,10SR)-2,2,3,10-Tetra­bromo-1,2,3,4-tetra­hydro-1,4-ethano­naphthalene, C12H10Br4, (I), is the first structure to be reported with four Br atoms bound to a 1,4-ethano­naphthalene framework and also the first which possesses three Br atoms in exo positions. Inter­actions between the Br atoms [three short intra­molecular Br...Br distances of 3.1094 (4), 3.2669 (4) and 3.4415 (5) Å] have little effect on the C-C bond lengths but lead to significant twisting of the cage structure compared with the parent hydro­carbon, which is expected to be fully eclipsed at the two saturated C2H4 bridge positions. Chemically related (1SR,4RS)-2,3-dibromo-1,4-etheno­naphthalene, C12H8Br2, (II), obtained by double dehydro­bromination of (I), represents the first structure of any halogen-substituted benzobarrelene. This cis-dibromide shows little evidence of steric congestion at the double bond [Br...Br = 3.5276 (8) Å] as a consequence of the large C-C-Br angles [average C=C-Br angle = 126.15 (10)°].

Formula: C12H10Br4 and C12H8Br2

hkldisplay filedownload file

Structure factor file (CIF format) (150.8 kbytes)
[ doi:10.1107/S010827011300231X/gz3227Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format) (116.9 kbytes)
[ doi:10.1107/S010827011300231X/gz3227IIsup3.hkl ]
Contains datablock II


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