title: Three 1-phenylindolin-2-one derivatives displaying different molecular dipole moments and different crystallographic symmetries.
abstract: Three 1-phenylindolin-2-one derivatives, namely 1-phenylindolin-2-one, C14H11NO, (I), 5-bromo-1-phenylindolin-2-one, C14H10BrNO, (II), and 5-iodo-1-phenylindolin-2-one, C14H10INO, (III), have been synthesized and their structures determined. Compounds (I) and (II) crystallized in the centrosymmetric space groups Pbca and P21/c, respectively, while compound (III) crystallized in the polar space group Aea2. Density functional theory (DFT) calculations show that the molecular dipole moment gradually decreases in the order (I) > (II) > (III). The relatively smaller dipole moment of (III) and the larger non-electrostatic intermolecular interactions may be the main reasons for the noncentrosymmetric and polar structure of (III).
authors.affiliation: School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China.
authors.forename: Lei
authors.initials: L
authors.lastname: Wang
authors.affiliation: School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China.
authors.forename: Man
authors.initials: M
authors.lastname: Zhang
authors.affiliation: School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China.
authors.forename: Ying Ying
authors.initials: YY
authors.lastname: Jin
authors.affiliation: State Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, People's Republic of China.
authors.forename: Qing
authors.initials: Q
authors.lastname: Lu
authors.affiliation: State Key Laboratory of Crystal Materials, Shandong University, Jinan 250100, People's Republic of China.
authors.forename: Qi
authors.initials: Q
authors.lastname: Fang
mesh_terms: D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D011789:Quantum Theory
chemical_list: C000598940:1-phenylindolin-2-one; C000598942:5-bromo-1-phenylindolin-2-one; C000598943:5-iodo-1-phenylindolin-2-one; D007211:Indoles
keywords: 1-phenylindolin-2-one derivatives; crystal structure; crystallographic symmetry; density functional theory (DFT) calculations; dipole moment; intermolecular interactions; molecular polarity