Determination of crystal structures and tautomeric states of 2-ammoniobenzenesulfonates by laboratory X-ray powder diffraction
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Sándor L. Bekö
Abstract
The crystal structures of 4-chloro-5-methyl-2-ammoniobenzenesulfonate and of the corresponding derivatives 4,5-dimethyl- and 4,5-dichloro-2-ammoniobenzenesulfonates have been determined from laboratory X-ray powder diffraction data. The tautomeric state of all three compounds could also be unequivocally determined from laboratory data, using careful Rietveld refinements. The tautomeric state was confirmed by IR spectroscopy. The compounds are neither isostructural to each other nor to the 5-chloro-4-methyl derivate, despite the similar size of the chloro and methyl substituents. The influence of the chloro and methyl substituents on the packing and on the thermal stability is demonstrated. All crystal structures were confirmed by dispersion-corrected DFT calculations. For the 4-chloro-5-methyl and the 4,5-dichloro derivatives the DFT calculations indicated that the observed polymorph should not be the thermodynamical one. However, no other polymorphs could be found in experimental polymorph screening, even using seeding with the corresponding isostructural phases. Obviously the DFT methods need further improvements.
Article note
In memoriam Dr. Erich F. Paulus (Hoechst AG).
Acknowledgments
We thank Silke D. Gumbert (Goethe-University, Frankfurt) for the execution of some experiments and Edith Alig (Goethe-University, Frankfurt) for XRPD, IR, DSC and TGA measurements and Milan Rudloff and Christian Schwalb (Goethe-University, Frankfurt) for SEM measurements.
References
[1] M. Tremayne, B. M. Kariuki, K. D. M. Harris, Angew. Chem.1997, 109, 788, Angew. Chem. Int. Ed.Engl.1997, 35, 770.10.1002/ange.19971090724Suche in Google Scholar
[2] R. J. Cernik, A. K. Cheetham, C. K. Prout, D. J. Watkin, A. P. Wilkinson, B. T. M. Willis, J. Appl. Cryst.1991, 24, 222.10.1107/S0021889890013486Suche in Google Scholar
[3] M. Tremayne, Presentation given at the European Crystallographic Meeting ECM-27: Bergen, Norway: 7–11 August 2012.Suche in Google Scholar
[4] L. J. Thompson, R. S. Voguri, A. Cowell, L. Male, M. Tremayne, Acta Cryst.2010, C66, o421.10.1107/S0108270110027319Suche in Google Scholar
[5] R. E. Dinnebier, R. Von Dreele, P. W. Stephens, S. Jelonek, J. Sieler, J. Appl. Cryst.1999, 32, 761.10.1107/S0021889899005233Suche in Google Scholar
[6] S. L. Bekö, S. D. Thoms, J. Brüning, J. van de Streek, A. Lakatos, C. Glaubitz, M. U. Schmidt, Z. Kristallogr.2010, 225, 382.10.1524/zkri.2010.1259Suche in Google Scholar
[7] S. L. Bekö, J. W. Bats, M. U. Schmidt, Acta Cryst.2012, C68, o45.10.1107/S0108270112005252Suche in Google Scholar
[8] R. K. Harris, P. Jonson, K. J. Packer, Magn. Reson. Chem.1985, 23, 565.10.1002/mrc.1260230716Suche in Google Scholar
[9] W. Herbst, K. Hunger, Industrial Organic Pigments, 3rd ed., Wiley-VCH, Weinheim, 2004.10.1002/3527602429Suche in Google Scholar
[10] G. R. Desiraju, J. A. R. P. Sarma, Proc. Indian Acad. Sci. (Chem. Sci.)1986, 96, 599.10.1007/BF02936309Suche in Google Scholar
[11] S. S. Batsanov, Inorg. Mater.2001, 37, 871.10.1023/A:1011625728803Suche in Google Scholar
[12] A. Bondi, J. Phys. Chem.1964, 68, 441.10.1021/j100785a001Suche in Google Scholar
[13] S. C. Nyburg, C. H. Fearman, Acta Crystallogr., Sect. B: Struct. Sci.1985, 41, 274.10.1107/S0108768185002129Suche in Google Scholar
[14] S. N. Ivashevskaya, J. van de Streek, J. E. Djanhan, J. Brüning, E. Alig, M. Bolte, M. U. Schmidt, P. Blaschka, H. W. Höffken, P. Erk, Acta Crystallogr., Sect. B: Struct. Sci.2009, 65, 212.10.1107/S0108768109001827Suche in Google Scholar
[15] M. U. Schmidt, J. van de Streek, S. N. Ivashevskaya, Chem. Eur. J.2009, 15, 338.10.1002/chem.200801899Suche in Google Scholar
[16] J. Van de Streek, S. Motherwell, J. Appl. Cryst.2005, 38, 694.10.1107/S0021889805016754Suche in Google Scholar
[17] Stoe & Cie, WinXPOW, Version 2.23, Stoe & Cie, Darmstadt, Germany, 2005.Suche in Google Scholar
[18] A. March, Z. Kristallogr.1932, 81, 285.10.1524/zkri.1932.81.1.285Suche in Google Scholar
[19] W. A. Dollase, J. Appl. Cryst.1986, 19, 267.10.1107/S0021889886089458Suche in Google Scholar
[20] W. I. F. David, D. S. Sivia, J. Appl. Cryst.2001, 34, 318.10.1107/S0021889801004332Suche in Google Scholar
[21] A. Boultif, D. Louër, J. Appl. Cryst.1991, 24, 987.10.1107/S0021889891006441Suche in Google Scholar
[22] P. M. de Wolff, J. Appl. Cryst.1968, 1, 108.10.1107/S002188986800508XSuche in Google Scholar
[23] G. S. Smith, R. L. Snyder, J. Appl. Cryst.1979, 12, 60.10.1107/S002188987901178XSuche in Google Scholar
[24] G. S. Pawley, J. Appl. Cryst.1981, 14, 357.10.1107/S0021889881009618Suche in Google Scholar
[25] D. W. M. Hofmann, Acta Cryst.2002, B58, 489.10.1107/S0108768101021814Suche in Google Scholar
[26] A. J. Markvardsen, W. I. F. David, J. C. Johnson, K. Shankland, Acta Cryst.2001, A57, 47.10.1107/S0108767300012174Suche in Google Scholar
[27] C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, Rodriguez-L. Monge, R. Taylor, J. van de Streek, P. A. Wood, J. Appl. Cryst.2008, 41, 466.10.1107/S0021889807067908Suche in Google Scholar
[28] W. I. F. David, K. Shankland, J. van de Streek, E. Pidcock, W. D. S. Motherwell, J. C. Cole, J. Appl. Cryst.2006, 39, 910.10.1107/S0021889806042117Suche in Google Scholar
[29] A. A. Coelho, TOPAS Academic User Manual, Version 4.1, Coelho Software, Brisbane, Australia, 2007.Suche in Google Scholar
[30] S. L. Mayo, B. D. Olafson, W. A. Goddard III, J. Phys. Chem.1990, 94, 8897.10.1021/j100389a010Suche in Google Scholar
[31] Accelrys. Cerius2, Version 4.9, Accelrys Ltd, Cambridge, England, 2003.Suche in Google Scholar
[32] I. J. Bruno, J. C. Cole, M. Kessler, J. Luo, W. D. S. Motherwell, L. H. Purkis, B. R. Smith, R. Taylor, R. I. Cooper, S. E. Harris, A. G. Orpen, J. Chem. Inf. Comput. Sci.2004, 44, 2133.10.1021/ci049780bSuche in Google Scholar
[33] F. H. Allen, Acta Cryst.2002, B58, 380.10.1107/S0108768102003890Suche in Google Scholar
[34] Avant-garde Materials Simulation Deutschland GmbH, GRACE (the Generation, Ranking, and Charaterization Engine), Merzhauser Strasse 177, 79100 Freiburg, Germany.Suche in Google Scholar
[35] G. Kresse, J. Hafner, Phys. Rev. B.1993, 47, 558.10.1103/PhysRevB.47.558Suche in Google Scholar
[36] G. Kresse, J. Hafner, Phys. Rev. B.1994, 49, 14251.10.1103/PhysRevB.49.14251Suche in Google Scholar
[37] G. Kresse, J. Furthmüller, Comput. Mater. Sci.1996, 6, 15.10.1016/0927-0256(96)00008-0Suche in Google Scholar
[38] G. Kresse, J. Hafner, Phys. Rev. B. 1996, 54, 11169.10.1103/PhysRevB.54.11169Suche in Google Scholar
[39] M. A. Neumann, M.-A. Perrin, J. Phys. Chem. B. 2005, 109, 15531.10.1021/jp050121rSuche in Google Scholar
[40] L. Ganguly, C. I. Jose, A. B. Biswas, Spectrochim. Acta A.1968, 24, 215.10.1016/0584-8539(68)80063-7Suche in Google Scholar
[41] W. H. Evans, Spectrochim. Acta A.1974, 30, 543.10.1016/0584-8539(74)80094-2Suche in Google Scholar
[42] S. R. Hall, E. N. Maslen, Acta Cryst.1967, 22, 216.10.1107/S0365110X67000386Suche in Google Scholar
[43] M. A. Leonard, P. J. Squattrito, Acta Cryst.1997, C53, 648.10.1107/S0108270196015600Suche in Google Scholar
[44] J. A. P. R. Sarma, G. R. Desiraju, Acc. Chem. Res.1986, 19, 222.10.1021/ar00127a005Suche in Google Scholar
[45] N. Ramasubbu, R. Parathasarathy, P. Murray-Rust, J. Am. Chem. Soc.1986, 108, 4308.10.1021/ja00275a012Suche in Google Scholar
[46] S. L. Price, A. J. Stone, J. Lucas, R. S. Rowland, A. E. Thornley, J. Am. Chem. Soc.1994, 116, 4910.10.1021/ja00090a041Suche in Google Scholar
[47] V. R. Hathwar, T. N. Guru Row, J. Phys. Chem. A.2010, 114, 13434.10.1021/jp1100413Suche in Google Scholar
[48] J. van de Streek, M. A. Neumann, Acta Cryst. 2010, B66, 544.10.1107/S0108768110031873Suche in Google Scholar
[49] J. Van de Streek, M. A. Neumann, Acta Cryst.2014, B70, 1020.10.1107/S2052520614022902Suche in Google Scholar
[50] M. U. Schmidt, J. Brüning, J. Glinnemann, M. W. Hützler, P. Mörschel, S. N. Ivashevskaya, J. van de Streek, D. Braga, L. Maini, M. R. Chierotti, R. Gobetto, Angew. Chem. Int. Ed.2011, 50, 7924, Angew. Chem. 2011, 123, 8070.10.1002/anie.201101040Suche in Google Scholar
[51] U. R. Fogueri, S. Kozuch, A. Karton, J. M. L. Martin, J. Phys. Chem.2013, 117A, 2269.10.1021/jp312644tSuche in Google Scholar
[52] S. Kozuch, J. M. L. Martin, J. Comput. Chem. 2013, 34, 2327.Suche in Google Scholar
[53] A. I. Kitaigorodskii, Molecular Crystals and Molecules, Academic Press, New York, 1973.Suche in Google Scholar
©2015 by De Gruyter
Artikel in diesem Heft
- Frontmatter
- Graphical Synopsis
- Review Article
- Visualization and analysis of crystal structures using CrystalMaker software
- Inorganic Crystal Structures
- [NaCl][Cu(HSeO3)2], NaCl-intercalated Cu(HSeO3)2: synthesis, crystal structure and comparison with related compounds
- Intermediate-valent CeCoAl – a commensurate modulated structure with short Ce–Co distances
- Pressure-induced transformation processes in ferroelastic Pb3(P1–xAsxO4)2, x = 0 and 0.80
- Disorder, pseudo symmetry and photoluminescence properties of a new diphosphate K2Ba3(P2O7)2
- Organic and Metalorganic Crystal Structures
- Determination of crystal structures and tautomeric states of 2-ammoniobenzenesulfonates by laboratory X-ray powder diffraction
- [Fe(PNN-iPr)Br2]·xDCM: the first example of merotype-epitaxy of a molecular structure and its solvatomorph
Artikel in diesem Heft
- Frontmatter
- Graphical Synopsis
- Review Article
- Visualization and analysis of crystal structures using CrystalMaker software
- Inorganic Crystal Structures
- [NaCl][Cu(HSeO3)2], NaCl-intercalated Cu(HSeO3)2: synthesis, crystal structure and comparison with related compounds
- Intermediate-valent CeCoAl – a commensurate modulated structure with short Ce–Co distances
- Pressure-induced transformation processes in ferroelastic Pb3(P1–xAsxO4)2, x = 0 and 0.80
- Disorder, pseudo symmetry and photoluminescence properties of a new diphosphate K2Ba3(P2O7)2
- Organic and Metalorganic Crystal Structures
- Determination of crystal structures and tautomeric states of 2-ammoniobenzenesulfonates by laboratory X-ray powder diffraction
- [Fe(PNN-iPr)Br2]·xDCM: the first example of merotype-epitaxy of a molecular structure and its solvatomorph
