The title pull-push chromophores, 2-[4-(di-methyl-amino)-benzyl-idene]-1H-indene-1,3(2H)-dione, C18H15NO2 (ID[1]) and (E)-2-{3-[4-(di-methyl-amino)-phen-yl]allyl-idene}-1H-indene-1,3(2H)-dione, C20H17NO2 (ID[2]), have donor-π-bridge-acceptor structures. The mol-ecule with the short π-bridge, ID[1], is almost planar while for the mol-ecule with a longer bridge, ID[2], is less planar. The benzene ring is inclined to the mean plane of the 2,3-di-hydro-1H-indene unit by 3.19 (4)° in ID[1] and 13.06 (8)° in ID[2]. The structures of three polymorphs of compound ID[1] have been reported: the α-polymorph [space group P21/c; Magomedova & Zvonkova (1978 ▸). Kristallografiya, 23, 281-288], the β-polymorph [space group P21/c; Magomedova & Zvonkova (1980 ▸). Kristallografiya, 25 1183-1187] and the γ-polymorph [space group Pna21; Magomedova, Neigauz, Zvonkova & Novakovskaya (1980 ▸). Kristallografiya, 25, 400-402]. The mol-ecular packing in ID[1] studied here is centrosymmetric (space group P21/c) and corresponds to the β-polymorph structure. The mol-ecular packing in ID[2] is non-centrosymmetric (space group P21), which suggests potential NLO properties for this crystalline material. In both compounds, there is short intra-molecular C-H⋯O contact present, enclosing an S(7) ring motif. In the crystal of ID[1], mol-ecules are linked by C-H⋯O hydrogen bonds and C-H⋯π inter-actions, forming layers parallel to the bc plane. In the crystal of ID[2], mol-ecules are liked by C-H⋯O hydrogen bonds to form 21 helices propagating along the b-axis direction. The mol-ecules in the helix are linked by offset π-π inter-actions with, for example, a centroid-centroid distance of 3.9664 (13) Å (= b axis) separating the indene rings, and an offset of 1.869 Å. Spectroscopic and electrochemical measurements show the ability of these compounds to easily transfer electrons through the π-conjugated chain.
Keywords: NLO; crystal structure; donor–π-bridge–acceptor; indane derivatives; non-linear chromophores.
© Bogdanov et al. 2019.