TY - JOUR
T1 - Chalcogen Bond versus Halogen Bond
T2 - Changing Contributions in Determining the Crystal Packing of Dihalobenzochalcogenadiazoles
AU - Ishigaki, Yusuke
AU - Shimomura, Kai
AU - Asai, Kota
AU - Shimajiri, Takuya
AU - Akutagawa, Tomoyuki
AU - Fukushima, Takanori
AU - Suzuki, Takanori
N1 - Funding Information:
We thank Grant-in-Aid from MEXT and JSPS (Nos. 20H02719, 20K21184, 21H01912, 21H05468) Japan. Y.I. acknowledges Toyota Riken Scholar and the 2020 DIC Award in Synthetic Organic Chemistry, Japan. This work was also supported by the Research Program of “Five-star Alliance” in “NJRC Mater. & Dev.” MEXT.
Funding Information:
We thank Grant-in-Aid from MEXT and JSPS (Nos. 20H02719, 20K21184, 21H01912, 21H05468) Japan. Y.I. acknowledges Toyota Riken Scholar and the 2020 DIC Award in Synthetic Organic Chemistry, Japan. This work was also supported by the Research Program of "Five-star Alliance" in "NJRC Mater. & Dev." MEXT.
Publisher Copyright:
© 2022 The Chemical Society of Japan.
PY - 2022
Y1 - 2022
N2 - In the crystals of 4,7-dihalobenzo[c][1,2,5]chalcogenadiazoles, the molecules are connected by two competing secondary bonding interactions: chalcogen bond (ChB) and halogen bond (HaB). Because the strengths of ChB and HaB change according to the kind of chalcogen (E: S, Se, Te) and halogen (X: Cl, Br, I), their relative contributions in determining the crystal packing can also change. Six newly determined crystal structures as well as 3 previously reported structures can be categorized into two groups: ChB-dominant and HaB-dominant structures. HaB in which X = I is strong enough to dictate the crystal packing of compounds with E = S and Se, but not where E = Te, whereas HaB in which X = Cl or Br has little effect on ChB-dominant molecular networks in crystals. The observed changing contributions of ChB and HaB may be useful for designing new supramolecular synthons for crystal engineering.
AB - In the crystals of 4,7-dihalobenzo[c][1,2,5]chalcogenadiazoles, the molecules are connected by two competing secondary bonding interactions: chalcogen bond (ChB) and halogen bond (HaB). Because the strengths of ChB and HaB change according to the kind of chalcogen (E: S, Se, Te) and halogen (X: Cl, Br, I), their relative contributions in determining the crystal packing can also change. Six newly determined crystal structures as well as 3 previously reported structures can be categorized into two groups: ChB-dominant and HaB-dominant structures. HaB in which X = I is strong enough to dictate the crystal packing of compounds with E = S and Se, but not where E = Te, whereas HaB in which X = Cl or Br has little effect on ChB-dominant molecular networks in crystals. The observed changing contributions of ChB and HaB may be useful for designing new supramolecular synthons for crystal engineering.
KW - Chalcogenadiazole
KW - Crystal engineering
KW - Intermolecular interaction
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U2 - 10.1246/bcsj.20220008
DO - 10.1246/bcsj.20220008
M3 - Article
AN - SCOPUS:85128772239
SN - 0009-2673
VL - 95
SP - 522
EP - 531
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
IS - 3
ER -