Structure of phenacetin, C10H13NO2

Abstract

Abstract. Mr= 179.21, monoclinic, P21/c, a= 13.25 (2), b= 9.65 (1), c--7.81 (1) A, fl= 104.9 (5) °, V= 965 (2)/~3, Z = 4, Dm-~ 1.240 (4), Ox= 1.234 (3) Mg m -3, Cu K~t, 2 = 1.5418 A,, /1 = 0.66 mm -~, F(000) = 384, T = 300 K, R = 0.088 for 1459 observed reflections. The planes of the side groups O(7)C(8)C(9) and N(10)C(11)C(12)O(13) are tilted with respect to the plane of the benzene ring by 9 (1) and 29 (1) °, respectively. The nitrogen and oxygen atoms of the acetamido group from two symmetryrelated molecules are hydrogen bonded. The crystal structure is stabilized by hydrogen bonds and van der Waals forces.

Towards an understanding of the molecular mechanism of solvation of drug molecules: A thermodynamic approach by crystal lattice energy, sublimation, and solubility exemplified by paracetamol, acetanilide, and phenacetin

“…The packing architectures for the considered drugs from the literature7,18,21 are shown in Figure 2. The molecular packing architectures for acetanilide and phenacetin in the crystal lattices are similar, because both molecules can create two hydrogen bonds.…”

“…However, works devoted to the temperature dependence of the solubility and calculation of the thermodynamic parameters are only few 17,20. For phenacetin only one article describes the crystal structure from X‐ray diffraction experiments,21 and several works are devoted to the temperature dependence of solubility 13,20. In order to predict transport through membranes and distribution between different compartments, it is common practice to use n‐octanol as a model for lipophilic phases such as biomembranes.…”

Partial molar volumes of some drug and pro-drug substances in 1-octanol at T=298.15K

“…To analyze the partial molar volumes, we used molecular volumes of the investigated compounds in the crystal lattices ðV mol 2 Þ which were calculated on the basis of X-ray data [6][7][8][9][10][11][12][13][14][15][16][17][18].…”

“…The choice of the substances was determined by the following reasons. Firstly, for the compounds under study the crystal structures were identified and the results were published in the earlier publications [6][7][8][9][10][11][12][13][14][15][16][17][18]. This fact gives an opportunity to calculate molecular volumes in the solid state and compare them with the analogous values for the solutions.…”

Toward polarizable AMOEBA thermodynamics at fixed charge efficiency using a dual force field approach: application to organic crystals

“…15 These compounds are shown in Figure 2 and include acetanilide, 68 paracetamol (polymorph I), 69 methyl paraben (polymorph II), 70 ethyl paraben, 71 and phenacetin. 72 Experimental lattice parameters and the space group for each compound are given in Table 1, along with asymmetric unit composition and unit cell volume in Table 2. The deposition free energy values from the prior study, computed using AMOEBA directly, will be compared to the three step DFF thermodynamic path that combines FC phase transitions and DFF corrections.…”