%0 Generic %A Saha, Binoy K. %A Nangia, Ashwini %A Nicoud, Jean-François %D 2006 %T Using Halogen···Halogen Interactions to Direct Noncentrosymmetric Crystal Packing in Dipolar Organic Molecules %U https://acs.figshare.com/articles/dataset/Using_Halogen_Halogen_Interactions_to_Direct_Noncentrosymmetric_Crystal_Packing_in_Dipolar_Organic_Molecules/3077275 %R 10.1021/cg060117k.s010 %2 https://acs.figshare.com/ndownloader/files/4783072 %K noncentrosymmetric space groups %K 5.0 D %K alignment %K nonlinear %K probability %K crystallization %K achiral molecules %K Br %K Interaction %K Direct Noncentrosymmetric Crystal Packing %K material %K moment %K Dipolar Organic MoleculesHalogen atoms Cl %K interhalogen interactions %K interhalogen interaction %K antiparallel %X Halogen atoms Cl, Br, and I steer crystallization of 2-halo-3-hydroxypyridine 1, pyridine-N-oxides 2, and 2-halo-3-aminopyridine 3 in noncentrosymmetric space groups efficient for nonlinear optical materials. Whereas the strong hydrogen-bond chains are aligned antiparallel, the L- or V-geometry of weak interhalogen interaction steers polar alignment in the solid state, even for high dipole moment (μ) halogenated N-oxides 2 (μ > 5.0 D). Six out of seven structures evaluated crystallize in polar/chiral space groups due to interhalogen interactions compared to the one in six probability of noncentrosymmetric packing for achiral molecules. %I ACS Publications