Acta Crystallographica Section C

Structural Chemistry

Volume 70, Part 4 (April 2014)


organic compounds



eg3152 scheme

Acta Cryst. (2014). C70, 400-404    [ doi:10.1107/S2053229614004999 ]

Three different fluoro- or chloro-substituted 1'-de­oxy-1'-phenyl-[beta]-D-ribo­furan­oses

J. W. Bats, A. Zivkovic, J. Parsch and J. W. Engels

Abstract: Crystal structures are reported for three fluoro- or chloro-substituted 1'-de­oxy-1'-phenyl-[beta]-D-ribo­furan­oses, namely 1'-de­oxy-1'-(2,4,5-tri­fluoro­phenyl)-[beta]-D-ribo­furan­ose, C11H11F3O4, (I), 1'-de­oxy-1'-(2,4,6-tri­fluoro­phenyl)-[beta]-D-ribo­furan­ose, C11H11F3O4, (II), and 1'-(4-chloro­phenyl)-1'-de­oxy-[beta]-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...[pi] 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.

CCDC references: 990051, 990052 and 990053

Formula: Two isomers of C11H11F3O4, and C11H13ClO4

Keywords: crystal structure; nucleic acids; [beta]-D-ribo­furan­ose; hydrogen bonding; crystal-packing effects.


hkldisplay filedownload file

Structure factor file (CIF format) (94.7 kbytes)
[ doi:10.1107/S2053229614004999/eg3152Isup2.hkl ]
Contains datablock I


hkldisplay filedownload file

Structure factor file (CIF format) (110.9 kbytes)
[ doi:10.1107/S2053229614004999/eg3152IIsup3.hkl ]
Contains datablock II


hkldisplay filedownload file

Structure factor file (CIF format) (204.1 kbytes)
[ doi:10.1107/S2053229614004999/eg3152IIIsup4.hkl ]
Contains datablock III


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