Three different fluoro- or chloro-substituted 1'-deoxy-1'-phenyl-β-D-ribofuranoses.
Crystal structures are reported for three fluoro- or chloro-substituted 1'-deoxy-1'-phenyl-β-D-ribofuranoses, namely 1'-deoxy-1'-(2,4,5-trifluorophenyl)-β-D-ribofuranose, C11H11F3O4, (I), 1'-deoxy-1'-(2,4,6-trifluorophenyl)-β-D-ribofuranose, C11H11F3O4, (II), and 1'-(4-chlorophenyl)-1'-deoxy-β-D-ribofuranose, C11H13ClO4, (III). The five-membered furanose ring of the three compounds has a conformation between a C2'-endo,C3'-exo twist and a C2'-endo envelope. The ribofuranose groups of (I) and (III) are connected by intermolecular O-H···O hydrogen bonds to six symmetry-related molecules to form double layers, while the ribofuranose group of (II) is connected by O-H···O hydrogen bonds to four symmetry-related molecules to form single layers. The O···O contact distance of the O-H···O hydrogen bonds ranges from 2.7172 (15) to 2.8895 (19) Å. Neighbouring double layers of (I) are connected by a very weak intermolecular C-F···π contact. The layers of (II) are connected by one C-H···O and two C-H···F contacts, while the double layers of (III) are connected by a C-H···Cl contact. The conformations of the molecules are compared with those of seven related molecules. The orientation of the benzene ring is coplanar with the H-C1' bond or bisecting the H-C1'-C2' angle, or intermediate between these positions. The orientation of the benzene ring is independent of the substitution pattern of the ring and depends mainly on crystal-packing effects.
Institut für Organische Chemie und Chemische Biologie, Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany.
Jan W
JW
Bats
Institut für Organische Chemie und Chemische Biologie, Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany.
Aleksandra
A
Żivković
Institut für Organische Chemie und Chemische Biologie, Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany.
Jörg
J
Parsch
Institut für Organische Chemie und Chemische Biologie, Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany.
Joachim W
JW
Engels
D018360:Crystallography, X-Ray; D003855:Deoxyribose / Q000031:analogs & derivatives* / Q000737:chemistry*; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*
C000589431:1'-(4-chlorophenyl)-1'-deoxy-beta-D-ribofuranose; C000589430:1'-deoxy-1'-(2,4,5-trifluorophenyl)-beta-D-ribofuranose; D009005:Monosaccharides; D003855:Deoxyribose
crystal structure; crystal-packing effects; hydrogen bonding; nucleic acids; β-d-ribofuranose