Unique halogen–π association detected in single crystals of C–N atropisomeric N-(2-halophenyl)quinolin-2-one derivatives and the thione analogue

Mai Uchibori, Nanami Murate, Kanako Shima, Tatsunori Sakagami, Ko Kanehisa, Gary James Richards, Akiko Hori and Osamu Kitagawa

Beilstein J. Org. Chem. 2025, 21, 1748–1756. https://doi.org/10.3762/bjoc.21.138

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Calculated using the Chemistry Development Kit 2.12

Property Name	Property Value
Molecular Formula	C₁₅H₁₀BrNS
Molecular Weight	316.22 g/mol
Exact Mass	314.9717 Da
InChI	InChI=1S/C15H10BrNS/c16-12-6-2-4-8-14(12)17-13-7-3-1-5-11(13)9-10-15(17)18/h1-10H
InChIKey	ZANPGNFIQJUFSL-UHFFFAOYSA-N
SMILES	C1=CC2=C(C=C1)N(C3=C(C=CC=C3)Br)C(=S)C=C2
Number of Atoms	28
Number of H-Bond Acceptors	1
Number of H-Bond Donors	0
Atoms in the Largest π-System	17
XLogP	3.1

Operator	Resulting query
aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)