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


To open or display or play some files, you may need to set your browser up to use the appropriate software. See the full list of file types for an explanation of the different file types and their related mime types and, where available links to sites from where the appropriate software may be obtained.

The download button will force most browsers to prompt for a file name to store the data on your hard disk.

Where possible, images are represented by thumbnails.

 bibliographic record in  format

  Find reference:   Volume   Page   
  Search:     From   to      Advanced search

Copyright © International Union of Crystallography
IUCr Webmaster