Crystal structure from laboratory X-ray powder diffraction data, DFT-D calculations, Hirshfeld surface analysis, and energy frameworks of a new polymorph of 1-benzothiophene-2-carboxylic acid

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.

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Powder Diffraction ◽

10.1017/s0885715620000755 ◽

2021 ◽

pp. 1-12

Author(s):

Analio J. Dugarte-Dugarte ◽

Jacco van de Streek ◽

Graciela Díaz de Delgado ◽

Alicja Rafalska-Lasocha ◽

José Miguel Delgado

Keyword(s):

Crystal Structure ◽

Carboxylic Acid ◽

Powder Diffraction ◽

Diffraction Data ◽

Rietveld Method ◽

Hirshfeld Surface ◽

Powder Diffraction Data ◽

Pharmacological Activities ◽

X Ray ◽

Acid Acid

Several benzothiophene-based compounds, including 1-benzothiophene-2-carboxylic acid, exhibit a wide variety of pharmacological activities. They have been extensively used to treat various types of diseases with high therapeutic effectiveness. In this contribution, the crystal structure of a new polymorph of 1-benzothiophene-2-carboxylic acid (BTCA) was determined from laboratory X-ray powder diffraction data with DASH, refined by the Rietveld method with TOPAS-Academic, and optimized using DFT-D calculations. The new form of 1-benzothiophene-2-carboxylic acid crystallizes in space group C2/c (No. 15) with a = 14.635(4), b = 5.8543(9), c = 19.347(3) Å, β = 103.95(1)°, V = 1608.8(6) Å3, and Z = 8. The structure is a complex 3D arrangement which can be described in terms of hydrogen-bonded dimers of BTCA molecules, joined by the acid–acid homosynthon, which interact through C–H⋯O hydrogen bonds to produce tapes further connected through head-to-tail π⋯π and edge-to-face C–H⋯π interactions. A comparison with a previously reported triclinic polymorph and with the related 1-benzofuran-2-carboxylic acid (BFCA) is also presented.

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C–H···O and C–H···X (X = Cl/Br) hydrogen bond tuned supramolecular assembly: a combined X-ray powder diffraction and Hirshfeld surface analysis

Powder Diffraction ◽

10.1017/s0885715614000128 ◽

2014 ◽

Vol 29 (3) ◽

pp. 280-288 ◽

Cited By ~ 1

Author(s):

Dipak K. Hazra ◽

Soumen Ghosh ◽

Paramita Chatterjee ◽

Somnath Ghosh ◽

Monika Mukherjee ◽

...

Keyword(s):

Surface Analysis ◽

Powder Diffraction ◽

Crystal Packing ◽

Three Dimensional ◽

Supramolecular Assembly ◽

Hirshfeld Surface ◽

Hirshfeld Surface Analysis ◽

Powder Diffraction Data ◽

X Ray ◽

Surface Areas

Crystal structures of N-(2-chlorophenyl) acetamide (1) and phenyl (2-bromomethyl) benzoate (2) have been determined from laboratory X-ray powder diffraction data. In addition to intermolecular N–H···O and C–H···O hydrogen bonds, the crystal packing in (1) and (2) exhibits weak C–H···Cl/Br interactions, which facilitate formation of three-dimensional architectures. Hirshfeld surface analysis of compounds (1), (2), and a few related chloro- and bromo-phenyl derivatives retrieved from the CSD indicates that 83–97% of Hirshfeld surface areas in this class of compounds are due to H···H, H···π, H···O, and H···Cl/Br contacts.

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Synthesis, X-ray crystal structure and BVS calculation of Co(II) complex of pyrimidine derived Schiff base ligand: Approached by Hirshfeld surface analysis and TDDFT calculation

Journal of Molecular Structure ◽

10.1016/j.molstruc.2021.130269 ◽

2021 ◽

Vol 1236 ◽

pp. 130269

Author(s):

Kinsuk Das ◽

Malay Dolai ◽

Sudipta Chatterjee ◽

Saugata Konar

Keyword(s):

Crystal Structure ◽

Schiff Base ◽

Surface Analysis ◽

Schiff Base Ligand ◽

Hirshfeld Surface ◽

Hirshfeld Surface Analysis ◽

X Ray

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Crystallographic study of ternary ordered skutterudite IrGe1.5Se1.5

Powder Diffraction ◽

10.1154/1.3478411 ◽

2010 ◽

Vol 25 (3) ◽

pp. 247-252 ◽

Cited By ~ 3

Author(s):

F. Laufek ◽

J. Návrátil

Keyword(s):

Crystal Structure ◽

Powder Diffraction ◽

Diffraction Data ◽

Rietveld Method ◽

Crystallographic Data ◽

Powder Diffraction Data ◽

X Ray ◽

Crystallographic Study ◽

Related Phase ◽

The Ideal

The crystal structure of skutterudite-related phase IrGe1.5Se1.5 has been refined by the Rietveld method from laboratory X-ray powder diffraction data. Refined crystallographic data for IrGe1.5Se1.5 are a=12.0890(2) Å, c=14.8796(3) Å, V=1883.23(6) Å3, space group R3 (No. 148), Z=24, and Dc=8.87 g/cm3. Its crystal structure can be derived from the ideal skutterudite structure (CoAs3), where Se and Ge atoms are ordered in layers perpendicular to the [111] direction of the original skutterudite cell. Weak distortions of the anion and cation sublattices were also observed.

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Preparation and crystal structure of garnet-type calcium zirconium germanate Ca4ZrGe3O12

Powder Diffraction ◽

10.1017/s0885715616000506 ◽

2016 ◽

Vol 31 (4) ◽

pp. 292-294 ◽

Cited By ~ 4

Author(s):

V. D. Zhuravlev ◽

A. P. Tyutyunnik ◽

N. I. Lobachevskaya

Keyword(s):

Crystal Structure ◽

Unit Cell Parameter ◽

Powder Diffraction ◽

Diffraction Data ◽

Cell Parameter ◽

Polycrystalline Sample ◽

Structural Formula ◽

Powder Diffraction Data ◽

Structural Refinement ◽

X Ray

A polycrystalline sample of Ca4ZrGe3O12 was synthesized using the nitrate–citrate method and heated at 850–1100 °C. Structural refinement based on X-ray powder diffraction data showed that the crystal structure is of the garnet type with a cubic unit-cell parameter [a = 12.71299(3) Å] and the space group Ia$\bar 3$d. The structural formula is presented as Ca3[CaZr]octa[Ge]tetraO12.

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