Supramolecular Architectures in 5,5 '-Substituted Hydantoins: Crystal Structures and Hirshfeld Surface Analyses
Oi, M; Park, JiH; Min, J; Lim, B; Lee, BH; Jung, G; Lee, JY; Karigar, CS; Yang, J; Chattopadhyay, B; Mukherjee, AK; Narendra, N; Hemantha, HP; Sureshbabu, VV; Helliwell, M; Mukherjee, M
| HERO ID | 7731673 |
|---|---|
| In Press | No |
| Year | 2010 |
| Title | Supramolecular Architectures in 5,5 '-Substituted Hydantoins: Crystal Structures and Hirshfeld Surface Analyses |
| Authors | Oi, M; Park, JiH; Min, J; Lim, B; Lee, BH; Jung, G; Lee, JY; Karigar, CS; Yang, J; Chattopadhyay, B; Mukherjee, AK; Narendra, N; Hemantha, HP; Sureshbabu, VV; Helliwell, M; Mukherjee, M |
| Journal | Crystal Growth & Design |
| Volume | 10 |
| Issue | 10 |
| Page Numbers | 4476-4484 |
| Abstract | A series of three 5,5â²-substituted hydantoin derivatives (1-3) were synthesized, and their crystal structures were solved using single-crystal synchrotron/powder-crystal X-ray diffraction data with a detailed analysis of Hirshfeld surfaces and fingerprint plots facilitating a comparison of intermolecular interactions in building different supramolecular architectures. A comparison of supramolecular assembly in the compounds with that in similar 5,5â²-substituted hydantoins in the Cambridge Structural Database (CSD) has been presented. The crystal packing in compounds 1-3 containing complementary hydrogen bonding groups, i.e. the amino NH donors and carbonyl O acceptors, exhibits three types of supramolecular synthons. In the dipropyl substituted hydantoin (1), intermolecular N-Hâ¯O hydrogen bonds with only one carbonyl O atom acting as a double acceptor generate a one-dimensional C 11(4)C11(4)[R2 2(8)] network propagating along the [100] direction, while in 3, a 5-spiro fused hydantoin, the cyclic R22(8) motifs self-organize through pairs of N-Hâ¯O hydrogen bonds to form a C 22(9)[R22(8)][R2 2(8)] framework running along the [1-10] direction. The molecular assembly in 2, with a dibutyl substitution at the hydantoin C-5 position, produces R44(17) synthons, which are edge-fused to form two-dimensional molecular sheets in the (100) plane. The formation of a supramolecular architecture built with an R44(17) synthon is unprecedented among the substituted hydantoin structures in the CSD. © 2010 American Chemical Society. |
| Doi | 10.1021/cg100706n |
| Wosid | WOS:000282535800042 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Scopus URL: https://www.scopus.com/inward/record.uri?eid=2-s2.0-77957690698&doi=10.1021%2fcg100706n&partnerID=40&md5=233b9263a4e76197fd805602c066bfee |
| Is Public | Yes |
| Language Text | English |