%0 Journal Article %1 Bekoe2012c %A Bekö, Sándor L. %A Bats, Jan W. %A Schmidt, Martin U. %D 2012 %I International Union of Crystallography %J Acta Crystallographica Section C %K 2-ammonio-5-chloro-4-methylbenzenesulfonat tautomeric-form %N 2 %P o45--o50 %R 10.1107/s0108270111054205 %T 2-Ammonio-5-chloro-4-methyl\-benzene\-sulfonate, its 1-methyl-2-pyrrolidone and dimethyl sulfoxide monosolvates and a corrected structure of 2,2\$^\prime\$-(1,4-phenyl\-ene)di(4,5-di\-hydro\-imidazolium) bis\-(4-aminobenzene\-sulfonate) dihydrate %U http://dx.doi.org/10.1107/s0108270111054205 %V 68 %X 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 Bek&\#246;, Thoms, Br&\#252;ning, Alig, van de Streek, Lakatos, Glaubitz & Schmidt (2010). Z. Kristallogr. 225, 382&\#19;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&\#183;C5H9NO, (Ib), and 2-ammonio-5-chloro-4-methylbenzenesulfonate dimethyl sulfoxide monosolvate, C7H8ClNO3S&\#183;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. E65, o2221&\#19;o2222 is corrected; it actually contains 4-aminobenzenesulfonate anions and 2,22-(1,4-phenylene)di(dihydroimidazolium) dications, i.e. 2,22-(1,4-phenylene)di(4,5-dihydroimidazolium) bis(4-aminobenzenesulfonate) dihydrate, C12H16N42+&\#183;2C6H6NO3S&\#18;&\#183;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.

@article{Bekoe2012c, 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 [Bek\&\#246;, Thoms, Br\&\#252;ning, Alig, van de Streek, Lakatos, Glaubitz \& Schmidt (2010). Z. Kristallogr. 225, 382\&\#19;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\&\#183;C5H9NO, (Ib), and 2-ammonio-5-chloro-4-methylbenzenesulfonate dimethyl sulfoxide monosolvate, C7H8ClNO3S\&\#183;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. E65, o2221\&\#19;o2222] is corrected; it actually contains 4-aminobenzenesulfonate anions and 2,22-(1,4-phenylene)di(dihydroimidazolium) dications, i.e. 2,22-(1,4-phenylene)di(4,5-dihydroimidazolium) bis(4-aminobenzenesulfonate) dihydrate, C12H16N42+\&\#183;2C6H6NO3S\&\#18;\&\#183;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.}}, added-at = {2019-03-11T21:00:05.000+0100}, author = {Bek{\"{o}}, S{\'{a}}ndor L. and Bats, Jan W. and Schmidt, Martin U.}, biburl = {https://www.bibsonomy.org/bibtex/28fbf19e2f18e2e6a87cce73cbded3e96/fairybasslet}, citeulike-article-id = {10205598}, citeulike-linkout-0 = {http://dx.doi.org/10.1107/s0108270111054205}, citeulike-linkout-1 = {http://scripts.iucr.org/cgi-bin/paper?S0108270111054205}, doi = {10.1107/s0108270111054205}, interhash = {fcfe0559e0a2ef7ec858ca09bb277586}, intrahash = {8fbf19e2f18e2e6a87cce73cbded3e96}, issn = {urn:issn:0108-2701}, journal = {Acta Crystallographica Section C}, keywords = {2-ammonio-5-chloro-4-methylbenzenesulfonat tautomeric-form}, month = feb, number = 2, pages = {o45--o50}, posted-at = {2013-11-01 19:53:42}, priority = {2}, publisher = {International Union of Crystallography}, timestamp = {2019-03-11T21:06:37.000+0100}, title = {{2-Ammonio-5-chloro-4-methyl{\-}benzene{\-}sulfonate, its 1-methyl-2-pyrrolidone and dimethyl sulfoxide monosolvates and a corrected structure of 2,2{\$^\prime\$}-(1,4-phenyl{\-}ene)di(4,5-di{\-}hydro{\-}imidazolium) bis{\-}(4-aminobenzene{\-}sulfonate) dihydrate}}, url = {http://dx.doi.org/10.1107/s0108270111054205}, volume = 68, year = 2012 }