Synthesis and crystal structures of (2E)-1,4-bis-(4-chloro-phen-yl)but-2-ene-1,4-dione and (2E)-1,4-bis-(4-bromo-phen-yl)but-2-ene-1,4-dione.

ABSTRACT: The mol-ecular structure of (2E)-1,4-bis-(4-chloro-phen-yl)but-2-ene-1,4-dione [C16H10Cl2O2, (1)] is composed of two p-chlorophenyl rings, each bonded on opposite ends to a near planar 1,4-trans enedione moiety [-C(=O)-CH=CH-(C=O)-] [r.m.s. deviation = 0.003?(1)?Å]. (2E)-1,4-Bis(4-bromo-phen-yl)but-2-ene-1,4-dione [C16H10Br2O2, (2)] has a similar structure to (1), but with two p-bromophenyl rings and a less planar enedione group [r.m.s. deviation = 0.011?(1)?Å]. Both mol-ecules sit on a center of inversion, thus Z' = 0.5. The dihedral angles between the ring and the enedione group are 16.61?(8) and 15.58?(11)° for (1) and (2), respectively. In the crystal, mol-ecules of (1) exhibit C-Cl?Cl type I inter-actions, whereas mol-ecules of (2) present C-Br?Br type II inter-actions. van der Waals-type inter-actions contribute to the packing of both mol-ecules, and the packing reveals face-to-face ring stacking with similar inter-planar distances of approximately 3.53?Å.

SUBMITTER: Lastovickova DN 

PROVIDER: S-EPMC5947802 | biostudies-other | 2018 Mar

REPOSITORIES: biostudies-other