title: Three trifluoromethyl-substituted protoporphyrinogen IX oxidase inhibitors.
abstract: The structures of methyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, C15H9ClF3N3O5, (I), methyl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzoate, C14H10ClF3N2O4, (II), and 2-[4-chloro-2-fluoro-5-(prop-2-ynyloxy)phenyl]-4-(trifluoromethyl)piperidine-2,6-dione, C15H10ClF4NO3, (III), are similar in their dihedral angles and in the distances between the farthest two atoms. There are two independent molecules in the structure of (I). The dihedral angles between the two aromatic rings in each molecule in (I), between the benzene and tetrahydropyrimidine rings in (II), and between the benzene ring and the five-atom planar portion of the piperidine-2,6-dione ring in (III) are 80.78 (11)/89.75 (11), 89.13 (9) and 87.52 (13) degrees , respectively. The distances between the farthest two atoms, viz. O...F in the two molecules of (I), and Cl...F in (II) and (III), are 11.763 (7)/11.953 (6), 10.734 (10) and 10.889 (9) A, respectively. In all three crystal structures, the molecules are linked to generate sheets of molecules via C-H...O interactions.
authors.affiliation: State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
authors.forename: Bin
authors.initials: B
authors.lastname: Li
authors.forename: Yu Ming
authors.initials: YM
authors.lastname: Lan
authors.forename: Chi Tung
authors.initials: CT
authors.lastname: Hsu
authors.forename: Zhen Long
authors.initials: ZL
authors.lastname: Liu
authors.forename: Hai Bin
authors.initials: HB
authors.lastname: Song
authors.forename: Chao
authors.initials: C
authors.lastname: Wu
authors.forename: Hua Zheng
authors.initials: HZ
authors.lastname: Yang
mesh_terms: D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000737:chemistry*; D006540:Herbicides / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D009579:Nitrobenzoates / Q000737:chemistry*; D010880:Piperidines / Q000737:chemistry*; D050768:Protoporphyrinogen Oxidase / Q000037:antagonists & inhibitors*; D011743:Pyrimidines / Q000737:chemistry*
chemical_list: D004791:Enzyme Inhibitors; D006540:Herbicides; D006845:Hydrocarbons, Fluorinated; D009579:Nitrobenzoates; D010880:Piperidines; D011743:Pyrimidines; D050768:Protoporphyrinogen Oxidase