2-[4-(Dimethylamino)phenyl]-3,3-difluoro-3<i>H</i>-naphtho[1,2-<i>e</i>][1,3,2]oxazaborinin-2-ium-3-uide

Dziuk, Błażej; Ośmiałowski, Borys; Skotnicka, Agnieszka; Ejsmont, Krzysztof; Zarychta, Bartosz

doi:10.1107/s2414314617011415

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“…The geometry around the boron atom is tetrahedral and the BF 2 -carrying ring is distorted from planarity. Nevertheless, it exhibits normal bond distances and angles (Lugo & Richards, 2010;Dziuk et al, 2017). The B-N distance [1.586 (3) Å ] is notably longer than a normal B1-N1 single bond (ca 1.52 Å ; Singh et al, 1986;Lugo & Richards, 2010), indicating weak bonding.…”

Section: Structure Descriptionmentioning

confidence: 99%

2,2-Difluoro-3-(4-fluorophenyl)-2H-benzo[e][1,3,2]oxazaborinin-3-ium-2-uide

et al. 2017

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There is one independent molecule in the asymmetric unit of the title compound, C 13 H 9 BF 3 NO, which crystallizes in the non-centrosymmetric space group Cc. In the molecular structure, the BF 2 -carrying ring is distorted from planarity and its mean plane makes a dihedral angle of 42.3 (1) with the 4-fluorophenyl ring. F atoms are involved in all of the short intermolecular contacts of the crystal structure, which link molecules to form chains along [001] and [010]. Structure descriptionSchiff bases containing a 2-OH group are molecules that are stabilized by intramolecular hydrogen bonding. These molecules act as chelating agents for many cations (Chohan et al., 2001;Topal et al., 2007). The exchange of the OH proton with a cationic species is relatively easy. The same is realised for the exchange of a proton by a strong Lewis acid (BF 2 group). Is such a case, the N/BF 2 interaction is much stronger than hydrogen bonding due to the high mobility of the proton. As a consequence, the BF 2 À derivatives do not lose excitation energy by vibration but fluoresce very intensively. Thus, salicaldehyde has been used several times to develop BF 2 -carrying fluorophores. These were reviewed by Ziessel and co-workers (Frath et al

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