Isomorphous crystal structures of chlorodi­acetyl­ene and iododi­acetyl­ene derivatives: simultaneous hydrogen and halogen bonds on carbon­yl

Acta Crystallographica Section E: Crystallographic Communications

Fan, V.¹  Tremblay, J.¹  Fortin, C.¹  Baillargeon, P.¹  Caron-Duval, É.¹  Rahem, T.¹  Blais, É.¹  Fortin, D.²  Dory, Y.L.³ 

[1] Département de Chimie, Cégep de Sherbrooke, 475 rue du Cégep, Sherbrooke, Québec, J1E 4K1, Canada;Laboratoire d'Analyses Structurales par Diffraction des Rayons-X, Département de Chimie, Université de Sherbrooke, 2500, boulevard de l'Université, Sherbrooke, Québec, J1K 2R1, Canada;Laboratoire de Synthèse Supramoléculaire, Département de Chimie, Institut de Pharmacologie, Université de Sherbrooke, 3001 12e avenue nord, Sherbrooke, QC, J1H 5N4, Canada

关键词: CRYSTAL STRUCTURE;    HALOGEN BOND;    HYDROGEN BOND;    CHLORODIACETYLENE;    IODODIACETYLENE;   

DOI  :  10.1107/S2056989017010155

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

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 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≡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≡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 inter­action and 13 structures for the similar C≡C—I⋯O=C inter­action).

【 授权许可】

CC BY