Acta Cryst. (2014). C70, 400-404 [ doi:10.1107/S2053229614004999 ]
Abstract: Crystal structures are reported for three fluoro- or chloro-substituted 1'-deoxy-1'-phenyl--D-ribofuranoses, namely 1'-deoxy-1'-(2,4,5-trifluorophenyl)--D-ribofuranose, C11H11F3O4, (I), 1'-deoxy-1'-(2,4,6-trifluorophenyl)--D-ribofuranose, C11H11F3O4, (II), and 1'-(4-chlorophenyl)-1'-deoxy--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-HO hydrogen bonds to six symmetry-related molecules to form double layers, while the ribofuranose group of (II) is connected by O-HO hydrogen bonds to four symmetry-related molecules to form single layers. The OO contact distance of the O-HO 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 contact. The layers of (II) are connected by one C-HO and two C-HF contacts, while the double layers of (III) are connected by a C-HCl 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.
CCDC references: 990051, 990052 and 990053
Formula: Two isomers of C11H11F3O4, and C11H13ClO4
Keywords: crystal structure; nucleic acids; -D-ribofuranose; hydrogen bonding; crystal-packing effects.
Structure factor file (CIF format) (94.7 kbytes)
Structure factor file (CIF format) (110.9 kbytes)
Structure factor file (CIF format) (204.1 kbytes)
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