In:
Acta Crystallographica Section C Structural Chemistry, International Union of Crystallography (IUCr), Vol. 73, No. 4 ( 2017-04-01), p. 343-349
Abstract:
Neutralization of 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridine with hydrohalo acids H X ( X = Cl and Br) yielded the pyridinium salts 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridinium chloride, C 9 H 10 F 4 NO + ·Cl − , (1), and 4-[(2,2,3,3-tetrafluoropropoxy)methyl]pyridinium bromide, C 9 H 10 F 4 NO + ·Br − , (2), both carrying a fluorous side chain at the para position of the pyridinium ring. Single-crystal X-ray diffraction techniques revealed that (1) and (2) are isomorphous. The halide anions accept four hydrogen bonds from N—H, ortho -C—H and CF 2 —H groups. Two cations and two anions form a centrosymmetric dimeric building block, utilizing complimentary N—H... X ...H—C sp 3 connections. These dimers are further crosslinked, utilizing another complimentary C sp 2 —H... X ...H—C sp 2 connection. The pyridinium rings are π-stacked, forming columns running parallel to the a axis that make angles of ca 44–45° with the normal to the pyridinium plane. There are also supramolecular C—H...F—C interactions, namely bifurcated C—H...F and bifurcated C—F...H interactions; additionally, one type II C—F...F—C halogen bond has been observed.
Type of Medium:
Online Resource
ISSN:
2053-2296
DOI:
10.1107/S2053229617004016
DOI:
10.1107/S2053229617004016/ku3194sup1.cif
DOI:
10.1107/S2053229617004016/ku3194i16197sup2.hkl
DOI:
10.1107/S2053229617004016/ku3194i16318sup3.hkl
Language:
Unknown
Publisher:
International Union of Crystallography (IUCr)
Publication Date:
2017
detail.hit.zdb_id:
2025703-X
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