TY - JOUR A1 - Orgzall, Ingo A1 - Lorenz, Bernd A1 - Mikat, Jürgen E. R. A1 - Reck, Günter A1 - Knochenhauer, Gerald A1 - Schulz, Burkhard T1 - Phase transition in 1,3,4-oxadiazole crystals under high pressure Y1 - 1998 ER - TY - JOUR A1 - Orgzall, Ingo A1 - Lorenz, Bernd A1 - Mikat, Jürgen E. R. A1 - Reck, Günter A1 - Knochenhauer, Gerald A1 - Schulz, Burkhard T1 - Phase transition in 1,3,4-oxadiazole crystals under high pressure N2 - Crystalline 2,5-di(4-nitrophenyl)-1,3,4-oxadiazole (DNO) has been investigated at pressures up to 5 GPa using Raman and optical spectroscopy as well as energy dispersive X-ray techniques. At ambient pressure DNO shows an orthorhombic unit cell (a = 0.5448 nm, b = 1.2758 nm, c = 1.9720 nm, density 1.513 g cm-3) with an appropriate space group Pbcn. From Raman spectroscopic investigations three phase transitions have been detected at 0.88, 1.28, and 2.2 GPa, respectively. These transitions have also been confirmed by absorption spectroscopy and X-ray measurements. Molecular modeling simulations have considerably contributed to the interpretation of the X-ray diffractograms. In general, the nearly flat structure of the oxadiazole molecule is preserved during the transitions. All subsequent structures are characterized by a stack-like arrangement of the DNO molecules. Only the mutual position of these molecular stacks changes due to the transformations so that this process may be described as a topotactical reaction. Phases II and III show a monoclinic symmetry with space group P21/c with cell parameters a = 1.990 nm, b = 0.500 nm, c = 1.240 nm, ß = 91.7°, density 1.681 g cm-3 (phase II, determined at 1. 1 GPa) and a = 1.890 nm, b = 0.510 nm, C = 1.242 nm, ß = 89.0°, density 1.733 g cm-3 (phase 111, determined at 2.0 GPa), respectively. The high-pressure phase IV stable at least up to 5 GPa shows again an orthorhombic structure with space group Pccn with corresponding cell parameters at 2.9 GPa: a = 0.465 nm, b = 1.920 nm, c = 1.230 nm and density 1.857 g cm-3 . For the first phase a blue pressure shift of the onset of absorption by about 0.032 eV GPa has been observed that may be explained by pressure influences on the electronic conjugation of the molecule. In the intermediate and high-pressure phases II-IV the onset of absorption shifts to increased wavelengths due to larger intermolecular interactions and enhanced excitation delocalization with decreasing intermolecular spacing. Y1 - 1999 ER - TY - JOUR A1 - Mikat, Jürgen E. R. A1 - Franco, Olga A1 - Regenstein, Wolfgang A1 - Reck, Günter A1 - Knochenhauer, Gerald A1 - Schulz, Burkhard A1 - Orgzall, Ingo T1 - 1,3,4-oxadiazole crystals under high pressure-phase transitions and properties Y1 - 2000 ER - TY - JOUR A1 - Franco, Olga A1 - Orgzall, Ingo A1 - Reck, Günter A1 - Stockhause, Sabine A1 - Schulz, Burkhard T1 - Structure and high-pressure behavior of 2,5-di-(4-aminophenyl)-1,3,4-oxadiazole N2 - The crystalline structures of two modifications of a compound containing the oxadiazole ring, 2,5-di-(4- aminophenyl)-1,3,4-oxadiazole (DAPO) were determined. One of these modifications contains water molecules in the crystal structure, which is observed for the first time for an oxadiazole crystal. Both crystals show an orthorhombic structure. The water free modification, DAPO L belongs to the space group Pbca (61) and has the lattice parameters: a = 13.461(5), b = 7.937(3) and c = 22.816(8) angstrom (CCDC 246608). The water containing pseudo-polymorph, DAPO 11, has the space group Cmcm (63) and the lattice parameters: a = 16.330(5), b = 12.307(2) and c = 6.9978(14) angstrom (CCDC 246609). To gain information on the inter molecular interactions within the crystals, X-ray experiments under compression at ambient temperature and under heating at vacuum conditions were performed. Neither DAPO I nor DAPO II undergo phase transitions in the ressure range up to 5 GPa, as could be concluded from X-ray and Raman experiments. X-ray and calorimetric studies indicate that DAPO II dehydrates into DAPO I under increasing temperature. Structural considerations suggest a two-stage process. The compression behavior of both substances is well described by the Murnaghan equation of state (MEOS) and the values of the bulk modulus and its pressure derivative are determined for these crystals. Additionally, in the case of DAPO I, also the thermal expansion coefficient an was measured. (c) 2005 Elsevier Ltd. All rights reserved Y1 - 2005 SN - 0022-3697 ER - TY - JOUR A1 - Emmerling, Franziska A1 - Orgzall, Ingo A1 - Reck, Günter A1 - Schulz, Burkhard W. A1 - Stockhause, Sabine A1 - Schulz, Burkhard T1 - Structures of substituted di-aryl-1, 3,4-oxadiazole derivatives: 2,5-bis(pyridyl)- and 2,5-bis(aminophenyl)-substitution JF - Journal of molecular structure N2 - Crystal structures of four different di-aryl-1,3,4-oxadiazole compounds (aryl = 2-pyridyl-, 3-pyridyl-, 2-aminophenyl-, 3-aminophenyl-) are determined. Crystallization of di(2-pyridyl)-1,3,4-oxadiazole yielded monoclinic and triclinic polymorphs. The structures are characterized by the occurrence of pi-pi interactions. Additionally, in case of the aminophenyl compounds intra- as well as intermolecular hydrogen bonds are found that influence the packing motif as well. Since these molecules are often used as ligands in metal-organic complexes similarities and differences of the molecular conformation between the molecules in the pure crystals and that of the ligands in the complexes are discussed. (c) 2006 Elsevier B.V. All rights reserved. KW - crystal structure KW - 1,3,4-oxadiazole KW - molecular conformation KW - hydrogen bonds Y1 - 2006 U6 - https://doi.org/10.1016/j.molstruc.2006.03.076 SN - 0022-2860 VL - 800 IS - 1-3 SP - 74 EP - 84 PB - Elsevier CY - Amsterdam ER -