caa a22 4500 463184068 CHVBK 20180406164847.0 cr unu---uuuuu 170326e20070601xx s 000 0 eng 10.1007/s10870-006-9160-y doi (NATIONALLICENCE)springer-10.1007/s10870-006-9160-y Synthesis and structural characterization of 2,5-dihalo-3,4-dinitrothiophenes [Elektronische Daten] [Li Wen, Seth Rasmussen] Using new nitration protocols, we have been able to efficiently dinitrate 2,5-dihalothiophenes with yields of ∼80-95%. The resulting products 2,5-dibromo-3,4-dinitrothiophene (1), 2,5-dichloro-3,4-dinitrothiophene (2), 2-bromo-5-chloro-3,4-dinitrothiophene (3), as well as the analogous 2-bromo-3,4-dinitrothiophene (4), all crystallize easily allowing their characterization via X-ray crystallography. Crystallization of 1 occurs in the monoclinic space group C2/c with a=14.547(3)Å, b=7.3534(15)Å, c=10.775(2)Å, β=128.89(3)°, and Z=4. Crystallization of 2 occurs in the tetragonal space group I-42d with a=9.9398(14)Å, b=9.9398(14)Å, c=16.866(3)Å, and Z=8. Crystallization of 3 occurs as a pseudo-merohedral twin in the triclinic space group P-1 with a=7.340(5)Å, b=8.094(5)Å, c=9.112(5)Å, α=82.059(5)°, β=66.232(5)°, γ=63.021(5)°, and Z=2. Crystallization of 4 occurs in the triclinic space group P-1 with a=7.1787(14)Å, b=7.4092(15)Å, c=8.3151(17)Å, α=101.67(3)°, β=96.00(3)°, γ=116.13(3)°, and Z=2. The structures of all compounds exhibit the formation of interesting solid-state assemblies due to halogen-bonding interactions between the halogen and nitro groups. Springer Science+Business Media, LLC, 2007 thiophene nationallicence halothiophene nationallicence nitration nationallicence halogen-bonding nationallicence Wen Li Department of Chemistry and Molecular Biology, North Dakota State University, 58105, Fargo, ND, USA aut Rasmussen Seth Department of Chemistry and Molecular Biology, North Dakota State University, 58105, Fargo, ND, USA aut Journal of Chemical Crystallography Kluwer Academic Publishers-Plenum Publishers; http://www.springer-ny.com 37/6(2007-06-01), 387-398 1074-1542 37:6<387 2007 37 10870 https://doi.org/10.1007/s10870-006-9160-y text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10870-006-9160-y text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Wen Li Department of Chemistry and Molecular Biology, North Dakota State University, 58105, Fargo, ND, USA aut NATIONALLICENCE 700 1- Rasmussen Seth Department of Chemistry and Molecular Biology, North Dakota State University, 58105, Fargo, ND, USA aut NATIONALLICENCE 773 0- Journal of Chemical Crystallography Kluwer Academic Publishers-Plenum Publishers; http://www.springer-ny.com 37/6(2007-06-01), 387-398 1074-1542 37:6<387 2007 37 10870 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer