TY - JOUR
T1 - Tris[2,2,6,6-tetramethyl-8-(trimethylsilyl)benzo[1,2- d;4,5- d ′]bis(1,3-dithiol)-4-yl]methanol diethyl ether monosolvate
AU - Fleck, Nico
AU - Schnakenburg, Gregor
AU - Filippou, Alexander C.
AU - Schiemann, Olav
N1 - Publisher Copyright:
© 2018 Fleck et al.
PY - 2018/4/1
Y1 - 2018/4/1
N2 - The title compound, a triarylmethanol, C46 H64 OS12 Si3 1, was synthesized via lithiation of tris-2,2,6,6-tetramethylbenzo[1,2-d;4,5-d′]bis[1,3]dithiol-4-yl-methanol, 2, and electrophilic quenching with trimethylsilyl chloride. The current crystal structure reveals information about the reactivity of this compound and compares well with the structure reported for the unsubstituted parent compound 2 [Driesschaert et al. (2012). Eur. J. Org. Chem. 33, 6517-6525]. The title compound 1 forms molecular propellers and crystallizes in P, featuring an unusually long Si - C ar bond of 1.910(3)Å. Moreover, the geometry at the central quaternary carbon is rather trigonal-pyramidal than tetrahedral due to vast intramolecular stress. One trimethylsilyl group is disordered over two positions in a 0.504(4):0.496(4) ratio and one S atom is disordered over two positions in a 0.509(7):0.491(7) ratio. The contribution of disordered diethyl ether solvent molecule(s) was removed using the PLATON SQUEEZE (Spek, 2015) solvent masking procedure. These solvent molecules are not considered in the given chemical formula and other crystal data.
AB - The title compound, a triarylmethanol, C46 H64 OS12 Si3 1, was synthesized via lithiation of tris-2,2,6,6-tetramethylbenzo[1,2-d;4,5-d′]bis[1,3]dithiol-4-yl-methanol, 2, and electrophilic quenching with trimethylsilyl chloride. The current crystal structure reveals information about the reactivity of this compound and compares well with the structure reported for the unsubstituted parent compound 2 [Driesschaert et al. (2012). Eur. J. Org. Chem. 33, 6517-6525]. The title compound 1 forms molecular propellers and crystallizes in P, featuring an unusually long Si - C ar bond of 1.910(3)Å. Moreover, the geometry at the central quaternary carbon is rather trigonal-pyramidal than tetrahedral due to vast intramolecular stress. One trimethylsilyl group is disordered over two positions in a 0.504(4):0.496(4) ratio and one S atom is disordered over two positions in a 0.509(7):0.491(7) ratio. The contribution of disordered diethyl ether solvent molecule(s) was removed using the PLATON SQUEEZE (Spek, 2015) solvent masking procedure. These solvent molecules are not considered in the given chemical formula and other crystal data.
KW - EPR
KW - crystal structure
KW - spin label
KW - triarylmethanol
KW - trityl radical
UR - http://www.scopus.com/inward/record.url?scp=85045071520&partnerID=8YFLogxK
U2 - 10.1107/S2056989018004516
DO - 10.1107/S2056989018004516
M3 - Article
AN - SCOPUS:85045071520
SN - 2056-9890
VL - 74
SP - 539
EP - 542
JO - Acta Crystallographica Section E: Crystallographic Communications
JF - Acta Crystallographica Section E: Crystallographic Communications
ER -