In:
Acta Crystallographica Section E Crystallographic Communications, International Union of Crystallography (IUCr), Vol. 73, No. 8 ( 2017-08-01), p. 1175-1179
Abstract:
The crystal structures of tert -butyl (5-chloropenta-2,4-diyn-1-yl)carbamate, C 10 H 12 ClNO 2 ( II ), and tert -butyl (5-iodopenta-2,4-diyn-1-yl)carbamate, C 10 H 12 INO 2 ( IV ), are isomorphous to previously reported structures and accordingly 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 (bifurcated N—H...O=C and C[triple-bond]C— X ...O=C interactions on the same carbonyl group). There is no long-range parallel stacking of diynes, so the topochemical polymerization of diacetylene is prevented. A Cambridge Structural Database search revealed that C[triple-bond]C— X ...O=C contacts shorter than the sum of the van der Waals radii are scarce (only one structure for the C[triple-bond]C—Cl...O=C interaction and 13 structures for the similar C[triple-bond] C—I...O=C interaction).
Type of Medium:
Online Resource
ISSN:
2056-9890
DOI:
10.1107/S2056989017010155
DOI:
10.1107/S2056989017010155/mw2133sup1.cif
DOI:
10.1107/S2056989017010155/mw2133IIsup2.hkl
DOI:
10.1107/S2056989017010155/mw2133IVsup3.hkl
Language:
Unknown
Publisher:
International Union of Crystallography (IUCr)
Publication Date:
2017
detail.hit.zdb_id:
2843762-7
detail.hit.zdb_id:
2041947-8
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