Acta Crystallographica Section B

Structural Science

Volume 56, Part 1 (February 2000)

Acta Cryst. (2000). B56, 58-67 [doi:10.1107/S0108768199009702]

Conformational preferences in 2-nitrophenylthiolates: interplay between intra- and intermolecular forces; structures of (E)-1-(4-methyl-2-nitrobenzenethiolato)-2-phenylethene, S-(2-nitrophenyl)benzenecarbothiolate and 1-(2-nitrophenylthio)-2,5-pyrrolidinedione

J. N. Low, E. J. Storey, M. McCarron, J. L. Wardell, G. Ferguson and C. Glidewell

Abstract: In (E)-1-(4-methyl-2-nitrobenzenethiolato)-2-phenylethene, C₁₅H₁₃NO₂S (1) (orthorhombic Pbca), the nitro group is almost coplanar with the adjacent aryl ring, but the dihedral angles between the nitro-aryl and styryl fragments is 121°. The molecules are linked by paired C-HO hydrogen bonds in a chain of rings. In S-(2-nitrophenyl)benzenecarbothiolate, C₁₃H₉NO₃S (2) (monoclinic P2₁/a), the nitro group is rotated by 33.0 (2)° out of the plane of the adjacent aryl ring and the thiobenzoate group is strongly twisted away from the plane of the disubstituted aryl ring. The molecules of (2) are linked into chains by C-HO hydrogen bonds, and each chain is linked to two neighbouring chains by means of aromatic [bold pi] stacking interactions. In 1-(2-nitrophenylthio)-2,5-pyrrolidinedione, C₁₀H₈N₂O₄S (3) (monoclinic P2₁/a), the nitro group is again almost coplanar with the adjacent aryl ring, but the pyrrolidinedione unit is almost orthogonal to the O₂NC₆H₄SN plane. There are three types of C-HO hydrogen bond in the structure, and these link the molecules into a two-dimensional net. The conformations of these molecules have been investigated by SCF calculations and two energy minima have been identified for each: the molecules of (1) and (3) adopt conformations in their crystals which are close to those at the overall energy minima calculated for isolated molecules, while molecules of (2) adopt a conformation in the crystal close to that calculated for the local energy minimum. Comparisons are made with the structures of some related compounds and it is concluded that, while the nature of the two conformational minima is determined by intramolecular forces, the choice between them is determined primarily by intermolecular forces.

Online 1 February 2000


	Structure factor file (CIF format) (149.5 kbytes) Contains datablock 1

	Structure factor file (CIF format) (110.7 kbytes) Contains datablock 2

	Structure factor file (CIF format) (120.5 kbytes) Contains datablock 3

Notes:

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.