Acta Crystallographica Section B

Structural Science, Crystal Engineering and Materials

Volume 70, Part 1 (February 2014)

crystal engineering

Acta Cryst. (2014). B70, 106-114    [ doi:10.1107/S2052520613022129 ]

Formation of isostructural solid solutions in 2,6-disubstituted N-phenylformamides and N-phenylthioamides

B. Omondi, A. Lemmerer, M. A. Fernandes, D. C. Levendis and M. Layh

Abstract: In order to investigate possible isostructural solid solutions of disubstituted N-phenylformamides and thioamides, we have studied the re-crystallization of pairs of compounds selected from 2,6-difluoro-N-phenylformamide (I), 2,6-dichloro-N-phenylformamide (II), 2,6-dimethyl-N-phenylformamide (III), 2,6-dichloro-N-phenylthioamide (IV), 2,6-dimethyl-N-phenylthioamide (V), 2,6-diisopropyl-N-phenylformamide (VI) and 2,6-diisopropyl-N-phenylthioamide (VII). For single-component 2,6-disubstituted-N-phenylformamides only the trans form occurs in the pure crystal, while for thioamides the cis form occurs, with only one exception. By forming solid solutions of pairs of these molecules the resulting structures all adopt similar N-H...O/S chains in the crystals. Solid solutions (1), (2) and (3), resulting from the mixing of (I) and (II), (II) and (III), and (IV) and (V), respectively, are all isostructural with each other (space group Pbca). Only co-crystal (1) is isostructural to both starting materials, while (2) is isostructural to only one of the starting pair, (II). Solid solution (3), which adopts the same Pbca structure as (1) and (2), is different to the monoclinic structures of both the reactants. Solid solution (4) is monoclinic, with similar hydrogen-bonded chains, and isostructural to the two components, resulting from the composition from the mixing of (VI) and (VII). Isostructural indices were used to quantify crystal-packing similarities and differences. Occupancy factors of the reactants in each co-crystal differ widely.

CCDC references: 985000, 985001, 985002 and 985003

Keywords: co-crystal; solid solution; isostructural; crystal engineering.

hkldisplay filedownload file

Structure factor file (CIF format) (87.4 kbytes)
[ doi:10.1107/S2052520613022129/gp50661sup2.hkl ]
Contains datablock 1

hkldisplay filedownload file

Structure factor file (CIF format) (71.4 kbytes)
[ doi:10.1107/S2052520613022129/gp50662sup3.hkl ]
Contains datablock 2

hkldisplay filedownload file

Structure factor file (CIF format) (102.8 kbytes)
[ doi:10.1107/S2052520613022129/gp50663sup4.hkl ]
Contains datablock 3

hkldisplay filedownload file

Structure factor file (CIF format) (146.9 kbytes)
[ doi:10.1107/S2052520613022129/gp50664sup5.hkl ]
Contains datablock 4


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