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Notable changes in the molecular conformations of 4-chlorobenzyl alcohol around the C(H 2 )-C ar  and O-C(H 2 ) bonds were found to take place at the first-order phase transition point (T c1  = 236 K). Quite similar phenomena were observed at T c1  (217 K) of the isomorphic 4-bromo compound. The two kinds of conformational changes are considered to couple and cause the reversal of the direction of the linear O-H. . . O hydrogen bond as the compound undergoes the first-order transition. The CH 2 OH moiety participates in several short intermolecular contacts, and a C-H. . .π interaction exists between the CH 2  and the neighboring phenyl group. These intermolecular factors seem to contribute to the regulation of the molecular conformation in the crystal. The C-O bond length of each compound shortens considerably at T &gt; T c1 .

Conformational Phase Transitions Associated with Reversal of Hydrogen Bond Direction in 4-Chloro- and 4-Bromobenzyl Alcohols. An X-Ray Study