Investigation and rationalisation of hydrogen bonding patterns in sulfonylamino compounds and related materials: crystal structure determination of microcrystalline solids from powder X-ray diffraction data

Abstract

The crystal structures of three sulfonylamino compounds have been solved ab initio using powder diffraction data collected using a conventional laboratory X-ray diffractometer, and refined using Rietveld profile-refinement techniques. 4-Toluenesulfonamide (1) is monoclinic, P2₁/n, with a= 7.7030(3), b= 16.4656(7), c= 6.5861(3)Å, β= 92.411(2)°; benzenesulfonylhydrazine (2) is monoclinic, P2₁/c, with a= 8.0924(2), b= 8.6082(2), c= 11.7122(4)Å, β= 108.591(2)°; and 4-toluenesulfonylhydrazine (3) is monoclinic, P2₁/n, with a= 18.6021(6), b= 5.6406(2), c= 8.5356(3)Å, β= 106.222(2)°. The structures of 1 and 2 were solved from powder X-ray diffraction data by direct methods, using the SHELXS and SIR88 programs respectively; the structure of 3 was solved from powder X-ray diffraction data by the combined maximum entropy and likelihood method. The hydrogen bonding patterns in these crystals, and in the crystal structures of some related sulfonylamino compounds, are analysed and classified according to recently developed methods based on graph set analysis. For 1, the hydrogen bonding is described by the graph set C(4)C(4); for 2, the graph set for the first-order network is N₁=C(5)S(5)C(4), and there are second-order networks R₄⁴(14) and R₄⁴(18); for 3, the first-order network is N₁=C(5)S(5)C(4).