2‐Ammonio‐5‐chloro‐4‐methylbenzenesulfonate,its 1‐methyl‐2‐pyrrolidone and dimethyl sulfoxide monosolvates and a corrected structure of 2,2′‐(1,4‐phenylene)di(4,5‐dihydroimidazolium) bis(4‐aminobenzenesulfonate) dihydrate |
| |
Authors: | Sndor L Bek Jan W Bats Martin U Schmidt |
| |
Abstract: | 2‐Ammonio‐5‐chloro‐4‐methylbenzenesulfonate, C7H8ClNO3S, (Ia), is an intermediate in the synthesis of lake red azo pigments. The present structure determination from single‐crystal data confirms the results of a previous powder diffraction determination Bekö, Thoms, Brüning, Alig, van de Streek, Lakatos, Glaubitz & Schmidt (2010). Z. Kristallogr. 225 , 382–387]. The zwitterionic tautomeric form is confirmed. During a polymorph screening, two additional pseudopolymorphs were obtained, viz. 2‐ammonio‐5‐chloro‐4‐methylbenzenesulfonate 1‐methyl‐2‐pyrrolidone monosolvate, C7H8ClNO3S·C5H9NO, (Ib), and 2‐ammonio‐5‐chloro‐4‐methylbenzenesulfonate dimethyl sulfoxide monosolvate, C7H8ClNO3S·C2H6OS, (Ic). The molecules of (Ib) have crystallographic m symmetry. The 1‐methyl‐2‐pyrrolidone solvent molecule has an envelope conformation and is disordered around the mirror plane. The structure shows hydrogen‐bonded ladders of molecules graph‐set notation C22(6)R22(12)] in the 010] direction. The benzene groups of adjacent ladders are also stacked in this direction. A different type of hydrogen‐bonded ladder graph‐set notation C(6)R22(4)R44(12)] occurs in (Ic). In (Ia), (Ib) and (Ic), the molecules correspond to the zwitterionic tautomer. The structure of the cocrystal of 4‐aminobenzenesulfonic acid with 1,4‐bis(4,5‐dihydroimidazol‐2‐yl)benzene Shang, Ren, Wang, Lu & Yang (2009). Acta Cryst. E 65 , o2221–o2222] is corrected; it actually contains 4‐aminobenzenesulfonate anions and 2,2′‐(1,4‐phenylene)di(dihydroimidazolium) dications, i.e. 2,2′‐(1,4‐phenylene)di(4,5‐dihydroimidazolium) bis(4‐aminobenzenesulfonate) dihydrate, C12H16N42+·2C6H6NO3S−·2H2O. Hence, all known structures of aminobenzenesulfonic acid complexes contain ionic or zwitterionic molecules; there is no known structure with a neutral aminobenzenesulfonic acid molecule. |
| |
Keywords: | |
|
|