Abstract
The crystal structures of tert-butyl (5-chloro-penta-2,4-diyn-1-yl)carbamate, C10H12ClNO2 (II), and tert-butyl (5-iodo-penta-2,4-diyn-1-yl)carbamate, C10H12INO2 (IV), are isomorphous to previously reported structures and accordingly their mol-ecular and supra-molecular structures are similar. In the crystals of (II) and (IV), mol-ecules are linked into very similar two-dimensional wall organizations with anti-parallel carbamate groups involved in a combination of hydrogen and halogen bonds (bifurcated N-H⋯O=C and C≡C-X⋯O=C inter-actions on the same carbonyl group). There is no long-range parallel stacking of diynes, so the topochemical polymerization of di-acetyl-ene is prevented. A Cambridge Structural Database search revealed that C≡C-X⋯O=C contacts shorter than the sum of the van der Waals radii are scarce (only one structure for the C≡C-Cl⋯O=C inter-action and 13 structures for the similar C≡C-I⋯O=C inter-action).
Highlights
Chemical contextHydrogen bonds (HBs) and halogen bonds (XBs) are considered to be useful noncovalent synthetic tools in crystal engineering (Aakeröy et al, 2015; Grabowski, 2016; Resnati et al, 2015; Cinčić et al, 2008)
Supporting information: this article has supporting information at journals.iucr.org/e a Département de Chimie, Cégep de Sherbrooke, 475 rue du Cégep, Sherbrooke, Québec, J1E 4K1, Canada, bLaboratoire d’Analyses Structurales par Diffraction des Rayons-X, Département de Chimie, Université de Sherbrooke, 2500, boulevard de l’Université, Sherbrooke, Québec, J1K 2R1, Canada, and cLaboratoire de Synthèse Supramoléculaire, Département de Chimie, Institut de Pharmacologie, Université de Sherbrooke, 3001 12e avenue nord, Sherbrooke, QC, The crystal structures of tert-butyl (5-chloropenta-2,4-diyn-1-yl)carbamate, C10H12ClNO2 (II), and tert-butyl (5-iodopenta-2,4-diyn-1-yl)carbamate, C10H12INO2 (IV), are isomorphous to previously reported structures and their molecular and supramolecular structures are similar
In the crystals of (II) and (IV), molecules are linked into very similar two-dimensional wall organizations with antiparallel carbamate groups involved in a combination of hydrogen and halogen bonds
Summary
Hydrogen bonds (HBs) and halogen bonds (XBs) are considered to be useful noncovalent synthetic tools in crystal engineering (Aakeröy et al, 2015; Grabowski, 2016; Resnati et al, 2015; Cinčić et al, 2008). These directional intermolecular interactions facilitate the preparation of the desired solid-state motifs and architectures (Gilday et al, 2015; Cavallo et al, 2016; Priimagi et al, 2013; Mukherjee et al, 2014; Shirman et al, 2015; Mukherjee et al, 2017).
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