Synthesis and crystal structures of (2 E )-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione and (2 E )-1,4-bis(4-bromophenyl)but-2-ene-1,4-dione

Journal Article · Mon Feb 12 23:00:00 EST 2018 · Acta Crystallographica Section E Crystallographic Communications

DOI:https://doi.org/10.1107/S205698901800230X· OSTI ID:1420344

Lastovickova, Dominika N.; La Scala, John J.; Sausa, Rosario C.

The molecular structure of (2 E )-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione [C ₁₆ H ₁₀ Cl ₂ O ₂ , ( 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]. (2 E )-1,4-Bis(4-bromophenyl)but-2-ene-1,4-dione [C ₁₆ H ₁₀ Br ₂ O ₂ , ( 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 molecules 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, 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.

• Sponsoring Organization: USDOE
• OSTI ID: 1420344
• Journal Information: Acta Crystallographica Section E Crystallographic Communications, Journal Name: Acta Crystallographica Section E Crystallographic Communications Journal Issue: 3 Vol. 74; ISSN ACSECI; ISSN 2056-9890
• Publisher: International Union of Crystallography (IUCr)
• Country of Publication: United Kingdom
• Language: English