3-(1H-Indol-3-yl)-2-(2-nitrobenzenesulfonamido)-propanoic acid including an unknown solvate

Islam Ullah Khan*, Hafiz Mubashar-Ur-Rehman, Salman Aziz, William T A Harrison

*Corresponding author for this work

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

In the title compound, C17H15N3O 6S, which crystallized with highly disordered methanol and/or water solvent molecules, the dihedral angle between the the indole and benzene ring systems is 5.3 (2)°, which allows for the formation of intramolecular π-π stacking interactions [centroid-centroid separations = 3.641 (3) and 3.694 (3) Å] and an approximate overall U-shape for the molecule. In the crystal, dimers linked by pairs of Ns - H⋯Oc (s = sulfonamide and c = carboxylate) hydrogen bonds generate R2 2(10) loops, whereas Ni - H⋯π (i = indole) interactions lead to chains propagating in [100] or [010]. Together, these lead to a three-dimensional network in which the solvent voids are present as intersecting (two-dimensional) systems of [100] and [010] channels. The title compound was found to contain a heavily disordered solvent molecule, which could be methanol or water or a mixture of the two. Due to its uncertain nature and the unresolvable disorder, the data were processed with the SQUEEZE option in PLATON [Spek (2009). Acta Cryst. D65, 148-155], which revealed 877.8 Å3 of solvent-accessible volume per unit cell and 126 electron-units of scattering density or 109.7 Å3 (16 electron units) per organic molecule. This was not included in the calculations of overall formula weight, density and absorption coefficient.

Original languageEnglish
Article numbero2019
Number of pages10
JournalActa Crystallographica Section E: Structure Reports Online
Volume68
Issue number7
Early online dateJul 2012
DOIs
Publication statusPublished - Jul 2012

Fingerprint

acids
Molecules
Acids
indoles
centroids
Methanol
molecules
methyl alcohol
Water
Sulfonamides
Dihedral angle
coefficients
Benzene
Dimers
water
carboxylates
dihedral angle
voids
absorptivity
Hydrogen bonds

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Materials Science(all)
  • Chemistry(all)

Cite this

3-(1H-Indol-3-yl)-2-(2-nitrobenzenesulfonamido)-propanoic acid including an unknown solvate. / Khan, Islam Ullah; Mubashar-Ur-Rehman, Hafiz; Aziz, Salman; Harrison, William T A.

In: Acta Crystallographica Section E: Structure Reports Online, Vol. 68, No. 7, o2019, 07.2012.

Research output: Contribution to journalArticle

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abstract = "In the title compound, C17H15N3O 6S, which crystallized with highly disordered methanol and/or water solvent molecules, the dihedral angle between the the indole and benzene ring systems is 5.3 (2)°, which allows for the formation of intramolecular π-π stacking interactions [centroid-centroid separations = 3.641 (3) and 3.694 (3) {\AA}] and an approximate overall U-shape for the molecule. In the crystal, dimers linked by pairs of Ns - H⋯Oc (s = sulfonamide and c = carboxylate) hydrogen bonds generate R2 2(10) loops, whereas Ni - H⋯π (i = indole) interactions lead to chains propagating in [100] or [010]. Together, these lead to a three-dimensional network in which the solvent voids are present as intersecting (two-dimensional) systems of [100] and [010] channels. The title compound was found to contain a heavily disordered solvent molecule, which could be methanol or water or a mixture of the two. Due to its uncertain nature and the unresolvable disorder, the data were processed with the SQUEEZE option in PLATON [Spek (2009). Acta Cryst. D65, 148-155], which revealed 877.8 {\AA}3 of solvent-accessible volume per unit cell and 126 electron-units of scattering density or 109.7 {\AA}3 (16 electron units) per organic molecule. This was not included in the calculations of overall formula weight, density and absorption coefficient.",
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