Carbamazepine Co-crystallization with Pyridine Carboxamides: Rationalization by Complementary Phase Diagrams and Crystal Energy Landscapes

被引:74
作者
Habgood, Matthew [2 ]
Deij, Menno A. [3 ]
Mazurek, Jaroslaw [3 ]
Price, Sarah L. [2 ]
ter Horst, Joop H. [1 ]
机构
[1] Delft Univ Technol, Intensified React & Separat Syst Proc & Energy La, NL-2628 CA Delft, Netherlands
[2] UCL, Dept Chem, London WC1H 0AJ, England
[3] Avantium Technol BV, NL-1014 BV Amsterdam, Netherlands
基金
英国工程与自然科学研究理事会;
关键词
STRUCTURE PREDICTION; CO-CRYSTALS; PHARMACEUTICAL COCRYSTALS; FLEXIBLE MOLECULES; POLYMORPHISM; CRYSTALLIZATION; NICOTINAMIDE; FLEXIBILITY; SOLIDS; AGENTS;
D O I
10.1021/cg901230b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Isonicotinamide (INA) co-crystallizes with carbamazepine (CBZ), as do nicotinamide (NA) and benzamide. The structure of CBZ-INA form II is solved from powder and is shown to be isostructural with CBZ-NA. However picolinamide (PA), despite its similarity to the other pyridine carboxamides in the homologous series, does not appear to form a co-crystal with CBZ, We compare and contrast the use of computed crystal energy landscapes and binary and ternary phase diagrams to explain this behavior. Two 1:1 co-crystal structures of CBZ and INA were predicted to have lower or comparable lattice energies than the sum of the pure component lattice energies. These structures corresponded to the known co-crystal structures. On the other hand, lattice energies of predicted CBZ-PA co-crystal structures were less stable than the pure component lattice energies, implying that CBZ and PA would not form a co-crystal. This is consistent with the experimental evidence. Examination of the hypothetical crystal structures for CBZ-INA and for CBZ-PA explains this in terms of intermolecular hydrogen-bonding capability. Thus computed crystal energy landscapes are more reliable than simple crystal engineering concepts in understanding co-crystal formation, and can provide a useful complement to experimental co-crystal screening.
引用
收藏
页码:903 / 912
页数:10
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