Crystal structure from X-ray powder diffraction data, DFT-D calculation, Hirshfeld surface analysis, and energy frameworks of (RS)-trichlormethiazide

Abstract

The structure of racemic (RS)-trichlormethiazide [systematic name: (RS)-6-chloro-3-(dichloromethyl)-1,1-dioxo-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide], C8H8Cl3N3O4S2 (RS-TCMZ), a diuretic drug used in the treatment of oedema and hypertension, was determined from laboratory X-ray powder diffraction data using DASH [David et al. (2006). J. Appl. Cryst. 39, 910–915.], refined by the Rietveld method with TOPAS-Academic [Coelho (2018). J. Appl. Cryst. 51, 210–218], and optimized using DFT-D calculations. The extended structure consists of head-to-tail dimers connected by π–π interactions which, in turn, are connected by C—Cl...π interactions. They form chains propagating along [101], further connected by N—H...O hydrogen bonds to produce layers parallel to the ac plane that stack along the b-axis direction, connected by additional N—H...O hydrogen bonds. The Hirshfeld surface analysis indicates a major contribution of H...O and H...Cl interactions (32.2 and 21.7%, respectively). Energy framework calculations confirm the major contribution of electrostatic interactions (E elec) to the total energy (E tot). A comparison with the structure of S-TCMZ is also presented.

Hydrogen bonding patterns and C—H...π interactions in the structure of the antiparkinsonian drug (R)-rasagiline mesylate determined using laboratory and synchrotron X-ray powder diffraction data

“…Within a project of the Grant-in-Aid program supported by the International Centre for Diffraction Data (ICDD) intended to register high-quality X-ray powder diffraction data of pharmaceutical materials of interest with none or limited structural information in the literature, several compounds of pharmaceutical and general chemical interest have been studied in our laboratory (Dugarte-Dugarte et al, 2021, 2022Toro et al, 2022). Since there is no structural information on rasagiline mesylate, it was decided to record its powder pattern and undertake the structure determination of this compound initially from laboratory data.…”

Crystalline Forms of 4,4'-Methylenediantipyrine: Crystallographic Unit Cell for the Anhydrous Form, from Laboratory Powder XRD Pattern by DASH Program Package

“…Laboratory pattern collections were also tested by the DASH package [12]. Several structures, obtained successfully with the help of the DASH program, are also reported for various crystalline pigments [13,14] and recently for (RS)-trichlormethiazide [15], when their diffraction patterns were measured only by laboratory X-ray tubes. Anhydrates of ezetimibe [16], morphine [17], naloxone hydrochloride and naltrexone hydrochloride [18] were also determined from laboratory powder diffraction data by application of DASH, where the initial molecular geometries were taken from the single-crystal structure of the monohydrates by excluding the water molecule.…”

Crystal structure from laboratory X-ray powder diffraction data, DFT-D calculations, and Hirshfeld surface analysis of (S)-dapoxetine hydrochloride

“…Within a project of the Grant-in-Aid program supported by the International Centre for Diffraction Data (ICDD) intended to register high-quality X-ray powder diffraction data of pharmaceutical materials of interest with none or limited structural information in the literature, several compounds of pharmaceutical and general chemical interest have been studied in our laboratory (Dugarte-Dugarte et al , 2021; Toro et al , 2022). Since there is no structural information on Dapoxetine hydrochloride, it was decided to record its powder pattern and undertake the structure determination of this compound from powder diffraction data.…”