TY - JOUR

T1 - Completing the picture of tolazamide polymorphism under extreme conditions

T2 - A low-temperature study

AU - Fedorov, Alexey Yu

AU - Rychkov, Denis A.

AU - Losev, Evgeniy A.

AU - Drebushchak, Tatiana N.

AU - Boldyreva, Elena V.

PY - 2019/5/1

Y1 - 2019/5/1

N2 - We present the results of an experimental and computational study of structural changes in two polymorphs of tolazamide {systematic name: 1-[(azepan-1-yl-amino)carbonyl]-4-methylbenzenesulfonamide}, C 14 H 21 N 3 O 3 S, on cooling to 100 K and reverse heating. No phase transitions occurred in this temperature range. The anisotropy of the thermal expansion was different for the two polymorphs and differed from that reported previously for the hydrostatic compression. The changes in different intermolecular contacts responsible for the strain anisotropy were analysed. Relative shortening of the contacts was related directly to their initial length and reversely to the steric density around them. Increasing steric density is likely to be the driving force for the conformational ordering of the azepane ring under compression.

AB - We present the results of an experimental and computational study of structural changes in two polymorphs of tolazamide {systematic name: 1-[(azepan-1-yl-amino)carbonyl]-4-methylbenzenesulfonamide}, C 14 H 21 N 3 O 3 S, on cooling to 100 K and reverse heating. No phase transitions occurred in this temperature range. The anisotropy of the thermal expansion was different for the two polymorphs and differed from that reported previously for the hydrostatic compression. The changes in different intermolecular contacts responsible for the strain anisotropy were analysed. Relative shortening of the contacts was related directly to their initial length and reversely to the steric density around them. Increasing steric density is likely to be the driving force for the conformational ordering of the azepane ring under compression.

KW - Cooling

KW - Crystal structure

KW - DFT calculations

KW - Disorder

KW - Hydrogen bond

KW - Intermolecular interactions

KW - Low temperature

KW - Polymorph

KW - Stacking

KW - X-RAY-DIFFRACTION

KW - VARIABLE-TEMPERATURE

KW - DISTORTION

KW - PHASE-TRANSITION

KW - polymorph

KW - TRANSFORMATION

KW - HIGH-PRESSURE

KW - III AMMINE COMPLEXES

KW - CRYSTAL-STRUCTURE

KW - intermolecular interactions

KW - low temperature

KW - HYDROGEN-BONDS

KW - disorder

KW - SINGLE-CRYSTAL

KW - cooling

KW - crystal structure

KW - hydrogen bond

KW - stacking

UR - http://www.scopus.com/inward/record.url?scp=85065494300&partnerID=8YFLogxK

U2 - 10.1107/S2053229619005217

DO - 10.1107/S2053229619005217

M3 - Article

C2 - 31062718

AN - SCOPUS:85065494300

VL - 75

SP - 598

EP - 608

JO - Acta Crystallographica Section C: Structural Chemistry

JF - Acta Crystallographica Section C: Structural Chemistry

SN - 2053-2296

IS - 5

ER -