Acta Crystallographica, Section C: Crystal Structure Communications p. o45-o50 (2012)
Update date:2022-07-29
Topics:
Bekoe, Sandor L.
Bats, Jan W.
Schmidt, Martin U.
2-Ammonio-5-chloro-4-methyl-benzene-sulfonate, C7H 8ClNO3S, (Ia), is an inter-mediate 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 [Bekoe, Thoms, Bruening, 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-methyl-ben-zene-sulfonate 1-methyl-2-pyrrolidone monosolvate, C7H8ClNO 3S·C5H9NO, (Ib), and 2-ammonio-5-chloro-4-methyl-benzene-sulfonate dimethyl sulfoxide monosolvate, C7H8ClNO3S·C2H6OS, (Ic). The mol-ecules of (Ib) have crystallo-graphic m symmetry. The 1-methyl-2-pyrrolidone solvent mol-ecule has an envelope conformation and is disordered around the mirror plane. The structure shows hydrogen-bonded ladders of mol-ecules [graph-set notation C22(6)R2 2(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)R4 4(12)] occurs in (Ic). In (Ia), (Ib) and (Ic), the mol-ecules correspond to the zwitterionic tautomer. The structure of the cocrystal of 4-amino-benzene-sulfonic acid with 1,4-bis-(4,5-dihydro-imidazol-2-yl)benzene [Shang, Ren, Wang, Lu & Yang (2009). Acta Cryst. E65, o2221-o2222] is corrected; it actually contains 4-amino-benzene-sulfonate anions and 2,2′-(1,4-phenyl-ene)di(dihydroimidazolium) dications, i.e. 2,2′-(1,4-phenyl-ene)di(4,5-dihydro-imidazolium) bis-(4-amino-benzene- sulfonate) dihydrate, C12H16N4 2+·2C6H6NO3S -·2H2O. Hence, all known structures of amino-benzene-sulfonic acid complexes contain ionic or zwitterionic mol-ecules; there is no known structure with a neutral amino-benzene-sulfonic acid mol-ecule.
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