Synthesis and crystal structures of (2E)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione and (2E)-1,4-bis(4-bromophenyl)but-2-ene-1,4-dione
Abstract
The molecular structure of (2E)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione [C16H10Cl2O2, (1)] is composed of twop-chlorophenyl rings, each bonded on opposite ends to a near planar 1,4-transenedione moiety [–C(=O)—CH=CH—(C=O)–] [r.m.s. deviation = 0.003 (1) Å]. (2E)-1,4-Bis(4-bromophenyl)but-2-ene-1,4-dione [C16H10Br2O2, (2)] has a similar structure to (1), but with twop-bromophenyl rings and a less planar enedione group [r.m.s. deviation = 0.011 (1) Å]. Both molecules sit on a center of inversion, thusZ′ = 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, molecules of (1) exhibit C—Cl...Cl type I interactions, whereas molecules of (2) present C—Br...Br type II interactions. van der Waals-type interactions contribute to the packing of both molecules, and the packing reveals face-to-face ring stacking with similar interplanar distances of approximately 3.53 Å.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Feb 13, 2018
- Source ID
- 10.1107/s205698901800230x
Entities
People
- Dominika N. Lastovickova
- John J. la Scala
- Rosario C. Sausa
Organizations
- Oak Ridge Institute for Science and Education
- United States Army Research Laboratory
- United States Department of Energy