Sulphone structures. Part II. Crystal and molecular structure of N-p-tolylsulphonylbenzylamine, 1-methyl-3-p-tolylsulphonylaminoindole, 1-methyl-3-p-tolylsulphonyliminoindoline-2-spirocyclopentane, and 1,2,3,4-tetrahydro-1,2,4-trimethyl-4-p-tolylsulphonylamino-3-p-tolylsulphonyliminoquinoline

Abstract

The crystal and molecular structures of the four title compounds have been determined by heavy-atom methods. (I): N-p-Tolylsulphonylbenzylamine, triclinic, a= 9·686, b= 9·156, c= 9·749 Å(all ±0·003 Å), α= 68·1, β= 64·5, γ= 60·5°(all ±0·1°), space group P, Z= 2. Four-circle diffractometer data, R 0·066 for 2515 independent reflections. (II): 1-Methyl-3-p-tolylsulphonylaminoindole, monoclinic, a= 20·69, b= 17·39, c= 9·53 Å(all ±0·01 Å), β= 118·25°± 0·03°, space group C2/c, Z= 8, linear diffractometer data, R 0·065 for 1948 independent reflections. (III): 1-Methyl-3-p-tolylsulphonyliminoindoline-2-spirocyclopentane, monclinic, a= 16·08, b= 11·42, c= 20·51 Å(all ±0·01Å), β= 105·0°± 0·1°, space group C2/c, Z= 8. Linear diffractometer data, R 0·055 for 1448 independent reflections. (IV): 1,2,3,4-Tetrahydro-1,2,4-trimethyl-4-p-tolylsulphonylamino-3-p-tolylsulphonylaminoquinoline, triclinic, a= 7·67 ± 0·01, b= 13·71 ± 0·02, c= 13·57 ± 0·02 Å, α= 110·4 ± 0·1, β= 109·2 ± 0·1, γ= 92·8 ± 0·2°, space group P, Z= 2. Visually estimated data, R 0·103 for 1481 independent reflections. In the four compounds the bond lengths and interbond angles at any sulphur atom are unaffected by the substituents at the nitrogen atom bonded to the sulphur atom. The bond lengths, but not the interbond angles, are the same for an sp² and an sp³ nitrogen atom and the angle between the planes through the O–S–O sulphonyl atoms and through the S–N–C atoms is restricted to the range 53–65 for an sp³ and 83–88° for an sp² nitrogen atom.