Structure determination and Hirshfeld surface analysis of new cocrystal and salt forms of 5-aminotetrazole with hydroxy- and nitro-substituted carboxylic acids

Jeyaraman Selvaraj Nirmal Ram*, Udhayasuriyan Sathya, Sundaramoorthy Gomathi, David Bradford Cordes

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

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Abstract

Two new crystalline solids, namely, 5-amino­tetra­zole–3,5-di­hydroxy­benzoic acid–water (1/4/6), CH3N5·4C7H6O4·6H2O (I), and 5-amino­tetra­zolium 3,5-di­nitro­salicylate, CH4N5+·C7H3N2O7− (II), have been synthesized and characterized by single-crystal X-ray diffraction and Hirshfeld surface analysis. The crystal packing arrangements of I and II are governed by N—H⋯O and O—H⋯O hydrogen-bonding inter­actions. In cocrystal I, adjacent acid mol­ecules are linked through O—H⋯O hydrogen bonds, forming a dimer with an R22(8) motif. In salt II, the tetra­zolium cation and acid anion are linked through N—H⋯O hydrogen bonds to also form a dimer with an R22(8) motif. Further N—H⋯O and O—H⋯O hydrogen bonds help to stabilize the crystal packing, along with aromatic π–π stacking inter­actions in I and carbon­yl⋯π inter­actions in II. The Hirshfeld surface analysis and fingerprint plots reveal that O⋯H/H⋯O inter­actions contribute 34.4% of the total inter­actions in the crystal packing of cocrystal I and 36.7% in salt II.
Original languageEnglish
Pages (from-to)414-423
Number of pages22
JournalActa Crystallographica Section C Structural Chemistry
Volume78
Issue numberPart 7
Early online date27 Jun 2022
DOIs
Publication statusE-pub ahead of print - 27 Jun 2022

Keywords

  • Intermolecular interaction
  • Crystal structure
  • Two-dimensional fingerprint plot
  • 5-aminotetrazole
  • Comparative analysis
  • Hirshfeld surface analysis

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