(1RS,2SR)-1,2,4,5,7-Pentabromo-5-methoxyindane

Abstract

In the title compound, C10H7Br5O, prepared by bromination of 5‐methoxy­indane, all bond lengths and angles are in the usual ranges. However, the relatively wide range of Br—C—C angles [107.2 (5)–117.0 (4)°] in the five‐membered ring may indicate repulsion between the neighbouring Br atoms. The crystal packing is stabilized by van der Waals interactions.

Lack of Cooperativity in the Triangular X3Halogen-Bonded Synthon?

“…For structures containing the Br 3 motif, all interaction energy values are in the range −15.08 (FEDSEN 64 refcode) to −4.14 kcal mol –1 (COCGEH 63 refcode), both structures containing trimers of nonsymmetrical aromatic derivatives. There is no correlation between the group a system belongs to and the interaction energy value, but the interaction energy is connected with the number and type of interactions between monomers forming the X 3 synthon.…”

“…There is no correlation between the group a system belongs to and the interaction energy value, but the interaction energy is connected with the number and type of interactions between monomers forming the X 3 synthon. For example, the trimer of lowest interaction energy present in the structure with the FEDSEN 64 refcode is stabilized not only due to three Br···Br contacts forming the Br 3 motif but also due to another Br···Br type II contact (shown in Figure 6 ). Similarly to systems containing the Cl 3 motif, also for trimers containing the Br 3 motif, dispersion is an important stabilizing factor but is less pronounced in this case.…”

Synthesis, Crystal and Molecular Structure of 2′,3′,3′-Tribromo-2′,3′-dihydrospiro[1,3-dioxolane-2,1′-indene]

“…The relatively wide range of the Br-C-C bond angles are within the range 108.6(7)-116.2(7)°and this may indicate repulsion between the neighbouring Br atoms. In a related structure (1RS,2SR)-1,2,4,5,7-pentabromo-5-methoxyindane [9], the five Br-C distances vary from 1.884 (7) (Table 1) [21].…”

“…Brominations of hydrocarbons are important processes in synthetic chemistry [6][7][8][9][10]. The materials obtained from bromination of hydrocarbons have numerous industrial applications as pesticides, plastics, fire retardants and pharmaceutical chemicals [11].…”