TY - JOUR

T1 - Effect of pressure on two polymorphs of tolazamide

T2 - Why no interconversion?

AU - Fedorov, A. Yu

AU - Rychkov, D. A.

AU - Losev, E. A.

AU - Zakharov, B. A.

AU - Stare, J.

AU - Boldyreva, E. V.

PY - 2017/4/28

Y1 - 2017/4/28

N2 - Two polymorphs of tolazamide, N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide, a sulfonylurea anti-diabetic drug, have different densities and molecular packings. Polymorph II converts into polymorph I in the solid state on heating or via recrystallization if solvent-assisted. The effect of pressure on the two forms and the possibility of a transformation to a denser form on compression have been studied. No phase transitions have been observed in either of the forms in a pentane-isopentane mixture (when no recrystallization is possible). Polymorph II recrystallized partly into a denser polymorph I in methanol at 0.1 GPa, but the transformation stopped at an early stage. Solid state DFT calculations of the two forms as well as conformational landscape investigation in the gas phase were used to rationalize this result. The anisotropic pressure-induced strain of the two polymorphs has been compared in relation to changes in the hydrogen bond geometry and the behavior of stacking interactions.

AB - Two polymorphs of tolazamide, N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide, a sulfonylurea anti-diabetic drug, have different densities and molecular packings. Polymorph II converts into polymorph I in the solid state on heating or via recrystallization if solvent-assisted. The effect of pressure on the two forms and the possibility of a transformation to a denser form on compression have been studied. No phase transitions have been observed in either of the forms in a pentane-isopentane mixture (when no recrystallization is possible). Polymorph II recrystallized partly into a denser polymorph I in methanol at 0.1 GPa, but the transformation stopped at an early stage. Solid state DFT calculations of the two forms as well as conformational landscape investigation in the gas phase were used to rationalize this result. The anisotropic pressure-induced strain of the two polymorphs has been compared in relation to changes in the hydrogen bond geometry and the behavior of stacking interactions.

KW - ORGANIC MOLECULAR-CRYSTALS

KW - INDUCED PHASE-TRANSITIONS

KW - TOTAL-ENERGY CALCULATIONS

KW - HARTREE-FOCK MODEL

KW - X-RAY-DIFFRACTION

KW - L-SERINE

KW - SINGLE-CRYSTAL

KW - INTERMOLECULAR INTERACTIONS

KW - HYDROSTATIC-PRESSURE

KW - DIFFERENT BEHAVIOR

UR - http://www.scopus.com/inward/record.url?scp=85018477120&partnerID=8YFLogxK

U2 - 10.1039/c6ce02527g

DO - 10.1039/c6ce02527g

M3 - Article

AN - SCOPUS:85018477120

VL - 19

SP - 2243

EP - 2252

JO - CrystEngComm

JF - CrystEngComm

SN - 1466-8033

IS - 16

ER -