TY - JOUR
T1 - Sp2CH⋯Cl hydrogen bond in the conformational polymorphism of 4-chloro-phenylanthranilic acid
AU - Liu, Meng
AU - Yin, Chuming
AU - Chen, Peng
AU - Zhang, Mingtao
AU - Parkin, Sean
AU - Zhou, Panpan
AU - Li, Tonglei
AU - Yu, Faquan
AU - Long, Sihui
N1 - Publisher Copyright:
© The Royal Society of Chemistry.
PY - 2017
Y1 - 2017
N2 - Chlorine can participate in numerous interactions such as halogen bonding, hydrogen bonding, and London dispersion in the solid state. In this work, we report the influence of a chlorine substituent on the polymorphism of a potential anticancer drug, 4-chloro-phenylanthranilic acid (CPAA). Three polymorphs have been discovered for this compound, and the three forms were characterized by single-crystal X-ray diffraction, power X-ray diffraction (PXRD), FT-IR, and Raman spectroscopy. Both conformational flexibility of the molecule and the sp2CH⋯Cl hydrogen bond seem to lead to the polymorphism of the system. The phase behavior was investigated by differential scanning calorimetry (DSC), with the conclusion that form II converts to III upon heating. A conformational scan shows the conformational minima corresponds to the conformers existing in the polymorphs. Lattice energy calculations show energies of -106.70, -104.72, and -194.42 kJ mol-1 for forms I to III, providing information on relative stability for each form. Hirshfeld analysis revealed that intermolecular interactions such as H⋯H, C⋯H, H⋯Cl, and H⋯O contribute to the stability of the crystal forms.
AB - Chlorine can participate in numerous interactions such as halogen bonding, hydrogen bonding, and London dispersion in the solid state. In this work, we report the influence of a chlorine substituent on the polymorphism of a potential anticancer drug, 4-chloro-phenylanthranilic acid (CPAA). Three polymorphs have been discovered for this compound, and the three forms were characterized by single-crystal X-ray diffraction, power X-ray diffraction (PXRD), FT-IR, and Raman spectroscopy. Both conformational flexibility of the molecule and the sp2CH⋯Cl hydrogen bond seem to lead to the polymorphism of the system. The phase behavior was investigated by differential scanning calorimetry (DSC), with the conclusion that form II converts to III upon heating. A conformational scan shows the conformational minima corresponds to the conformers existing in the polymorphs. Lattice energy calculations show energies of -106.70, -104.72, and -194.42 kJ mol-1 for forms I to III, providing information on relative stability for each form. Hirshfeld analysis revealed that intermolecular interactions such as H⋯H, C⋯H, H⋯Cl, and H⋯O contribute to the stability of the crystal forms.
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U2 - 10.1039/c7ce00772h
DO - 10.1039/c7ce00772h
M3 - Article
AN - SCOPUS:85026645055
SN - 1466-8033
VL - 19
SP - 4345
EP - 4354
JO - CrystEngComm
JF - CrystEngComm
IS - 30
ER -