Polymorphism and Phase Transformation Behavior of
Solid Forms of 4‑Amino-3,5-dinitrobenzamide
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Abstract
We report the preparation, analysis,
and phase transformation behavior
of polymorphs and the hydrate of 4-amino-3,5-dinitrobenzamide. The
compound crystallizes in four different polymorphic forms, Form I
(monoclinic, <i>P</i>2<sub>1</sub>/<i>n</i>),
Form II (orthorhombic, <i>Pbca</i>), Form III (monoclinic, <i>P</i>2<sub>1</sub>/<i>c</i>), and Form IV (monoclinic, <i>P</i>2<sub>1</sub>/<i>c</i>). Interestingly, a hydrate
(triclinic, <i>P</i>1̅) of the compound is also discovered
during the systematic identification of the polymorphs. Analysis of
the polymorphs has been investigated using hot stage microscopy, differential
scanning calorimetry, in situ variable-temperature powder X-ray diffraction,
and single-crystal X-ray diffraction. On heating, all of the solid
forms convert into Form I irreversibly, and on further heating, melting
is observed. In situ single-crystal X-ray diffraction studies revealed
that Form II transforms to Form I above 175 °C via single-crystal-to-single-crystal
transformation. The hydrate, on heating, undergoes a double phase
transition, first to Form III upon losing water in a single-crystal-to-single-crystal
fashion and then to a more stable polymorph Form I on further heating.
Thermal analysis leads to the conclusion that Form II appears to be
the most stable phase at ambient conditions, whereas Form I is more
stable at higher temperature