scholarly journals Hydrogen Bonds, Topologies, Energy Frameworks and Solubilities of Five Sorafenib Salts

2021 ◽  
Vol 22 (13) ◽  
pp. 6682
Author(s):  
Chiuyen Phan ◽  
Jie Shen ◽  
Kaxi Yu ◽  
Jiyong Liu ◽  
Guping Tang
Keyword(s):  
Crystal Structures ◽  
Water Solubility ◽  
Mixed Solvent ◽  
Kinase Inhibitor ◽  
Water Molecules ◽  
Cell Dimensions ◽  
Hydrochloride Monohydrate ◽  
Unit Cell Dimensions ◽  
Similar Unit ◽  
Methyl Phenyl

Sorafenib (Sor) is an oral multi-kinase inhibitor, but its water solubility is very low. To improve its solubility, sorafenib hydrochloride hydrate, sorafenib hydrobromide and sorafenib hydrobromide hydrate were prepared in the mixed solvent of the corresponding acid solution, and tetrahydrofuran (THF). The crystal structures of sorafenib hydrochloride trihydrate (Sor·HCl.3H2O), 4-(4-{3-[4-chloro-3-(trifluoro-methyl)phenyl]ureido}phenoxy)-2-(N-methylcarbamoyl) pyridinium hydrochloride trihydrate, C21H17ClF3N4O3+·Cl−.3H2O (I), sorafenib hydrochloride monohydrate (Sor·HCl.H2O), C21H17ClF3N4O3+·Cl−.H2O (II), its solvated form (sorafenib hydrochloride monohydrate monotetrahydrofuran (Sor·HCl.H2O.THF), C21H17ClF3N4O3+·Cl−.H2O.C4H8O (III)), sorafenib hydrobromide (Sor·HBr), 4-(4-{3-[4-chloro-3-(trifluoro-methyl)phenyl]ureido}phenoxy)-2-(N-methylcarbamoyl) pyridinium hydrobromide, C21H17ClF3N4O3+·Br− (IV) and sorafenib hydrobromide monohydrate (Sor·HBr.H2O), C21H17ClF3N4O3+·Br−.H2O (V) were analysed. Their hydrogen bond systems and topologies were investigated. The results showed the distinct roles of water molecules in stabilizing their crystal structures. Moreover, (II) and (V) were isomorphous crystal structures with the same space group P21/n, and similar unit cell dimensions. The predicted morphologies of these forms based on the BFDH model matched well with experimental morphologies. The energy frameworks showed that (I), and (IV) might have better tabletability than (II) and (V). Moreover, the solubility and dissolution rate data exhibited an improvement in the solubility of these salts compared with the free drug.

scholarly journals Isomorphous Crystals Formed by the Similar Supramolecular Motifs in Sorafenib Hydrochloride and Regorafenib Hydrochloride Salts

Crystals ◽  
2019 ◽  
Vol 9 (12) ◽  
pp. 649 ◽  
Author(s):  
Chi Uyen Phan ◽  
Jie Shen ◽  
Jiyong Liu ◽  
Jianming Mao ◽  
Xiurong Hu ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Crystal Structures ◽  
Pyridinium Cation ◽  
Supramolecular Motifs ◽  
Solubility Profile ◽  
Cell Dimensions ◽  
Unit Cell Dimensions ◽  
Similar Unit ◽  
Similar Crystal Structure

Sorafenib and regorafenib (or fluoro-sorafenib) are multikinase inhibitors active in the treatment of various human cancers, but their solubilities are very poor. To improve their solubilities, in this study, sorafenib hydrochloride (Sor·HCl, I) and regorafenib hydrochloride (Reg·HCl, II) have been prepared and their crystal structures were characterized. Their solubility properties in water were evaluated. Intriguingly, they are isomorphous crystal structures with the same space group and the similar unit cell dimensions, which were caused by the similar supramolecular patterns resulted by the formation of N–H···Cl− hydrogen bond instead of hydrogen bond between the protonated pyridinium cation and counterion. Moreover, the solubility properties displayed identical profiles. It may be concluded that a similar crystal structure leads to a comparable solubility profile.

Three isostructural solvates of a tetrahydrofurochromenone derivative

2017 ◽  
Vol 73 (5) ◽  
pp. 407-413 ◽  
Author(s):  
Balasubramanian Sridhar ◽  
Jagadeesh Babu Nanubolu ◽  
Krishnan Ravikumar ◽  
Govindaraju Karthik ◽  
Basi Venkata Subba Reddy
Keyword(s):  
Three Dimensional ◽  
Unit Cell ◽  
Multicomponent Systems ◽  
Two Dimensional ◽  
The Core ◽  
Cell Dimensions ◽  
Similarity Indices ◽  
Unit Cell Dimensions ◽  
Similar Unit ◽  
Crystal Packings

Isostructurality is more likely to occur in multicomponent systems. In this context, three closely related solvates were crystallized, namely, benzene (C27H21BrO6·C6H6), toluene (C27H21BrO6·C7H8) and xylene (C27H21BrO6·C8H10) with methyl 3a-acetyl-3-(4-bromophenyl)-4-oxo-1-phenyl-3,3a,4,9b-tetrahydro-1H-furo[3,4-c]chromene-1-carboxylate, and their crystal structures determined. All three structures belong to the same space group (P\overline{1}) and display similar unit-cell dimensions and conformations, as well as isostructural crystal packings. The isostructurality is confirmed by unit-cell and isostructural similarity indices. In each solvate, weak C—H...O and C—H...π interactions extend the molecules into two-dimensional networks, which are further linked by C—H...Br and Br...Br interactions into three-dimensional networks. The conformation of the core molecule is predominantly responsible for governing the isostructurality.

scholarly journals The crystal structures of two polyamides (‘nylons’)

1947 ◽  
Vol 189 (1016) ◽  
pp. 39-68 ◽  
Keyword(s):  
Crystal Structures ◽  
Unit Cell ◽  
Chain Molecule ◽  
X Ray Diffraction ◽  
X Ray ◽  
Cell Dimensions ◽  
C Fibre ◽  
Diffraction Patterns ◽  
Unit Cell Dimensions ◽  
Crystalline Forms

Detailed interpretations of the X -ray diffraction patterns of fibres and sheets of 66 and 6.10 polyamides (polyhexam ethylene adipamide and sebacamide respectively) are proposed. The crystal structures of the two substances are completely analogous. Fibres of these two polyam ides usually contain two different crystalline forms, α and β, which are different packings of geometrically similar molecules; most fibres consist chiefly of the α form. In the case of the 66 polymer, fibres have been obtained in which there is no detectable proportion of the β form. Unit cell dimensions and the indices of reflexions for the α form were determined by trial, using normal fibre photographs, and were checked by using doubly oriented sheets set at different angles to the X -ray beam. The unit cell of the a form is triclinic, with a — 4·9 A, b = 5·4 A, c (fibre axis) = 17·2A, α = 48 1/2º, β = 77º, γ = 63 1/2º for the 66 polymer; a = 4·95A, b = 5·4A, c (fibre axes) = 22·4A, α = 49º, β = 76 1/2º, γ = 63 1/2º for the 6.10 polymer. One chain molecule passes through the cell in both cases. Atomic coordinates in occrystals were determined by interpretation of the relative intensities of the reflexions. The chains are planar or very nearly so; the oxygen atoms appear to lie a little off the plane of the chain. The molecules are linked by hydrogen bonds between C = 0 and NH groups, to form sheets. A simple packing of these sheets of molecules gives the α arrangement.

Syntheses and crystal structures of Li(Ta0.89Ti0.11)O2.945 and (Li0.977Eu0.023)(Ta0.89Ti0.11)O2.968

2013 ◽  
Vol 28 (3) ◽  
pp. 178-183 ◽  
Author(s):  
Tomohiro Uchida ◽  
Shiho Suehiro ◽  
Toru Asaka ◽  
Hiromi Nakano ◽  
Koichiro Fukuda
Keyword(s):  
Crystal Structures ◽  
Maximum Entropy Method ◽  
Rietveld Method ◽  
Three Dimensional ◽  
Structural Models ◽  
Entropy Method ◽  
Density Distributions ◽  
Cell Dimensions ◽  
Conventional Structure ◽  
Unit Cell Dimensions

Crystal structures of Li(Ta0.89Ti0.11)O2.945 and (Li0.977Eu0.023)(Ta0.89Ti0.11)O2.968 were investigated by laboratory X-ray powder diffraction. Both title compounds were trigonal with space group R3c and Z = 6. The hexagonal unit-cell dimensions were a = 0.514 82 9(2) nm, c = 1.377 61 2(4) nm, and V = 0.316 21 6(2) nm3 for the former compound and a = 0.517 71 2(2) nm, c = 1.373 50 0(6) nm, and V = 0.318 81 2(3) nm3 for the latter. The initial structural models, being isostructural with LiTaO3, were refined by the Rietveld method. The maximum-entropy method-based pattern fitting (MPF) method was subsequently used to confirm the validity of the structural models, in which conventional structure bias caused by assuming intensity partitioning was minimized. Atomic arrangements of the final structural models were in excellent agreement with the three-dimensional electron-density distributions determined by MPF.

Crystal Structures and Thermal Behavior of Isostructural Bis(dibenzyldimethylammonium) Tetrachlorometallate [M = Mn(II), Co(II), Ni(II) and Zn(II)] Solvates Crystallized from Acetonitrile and/or Methanol Solutions

2007 ◽  
Vol 62 (1) ◽  
pp. 28-34 ◽  
Author(s):  
Sara Busi ◽  
Roland Fröhlich ◽  
Manu Lahtinen ◽  
Jussi Valkonen ◽  
Kari Rissanen
Keyword(s):  
Crystal Structures ◽  
Solvent Molecule ◽  
Monoclinic Space Group ◽  
Asymmetric Unit ◽  
Π Interactions ◽  
Copper Compounds ◽  
Methanol Solutions ◽  
Cell Dimensions ◽  
Unit Cell Dimensions ◽  
Weak Edge

Five isostructural bis(dibenzyldimethylammonium) tetrachlorometallate solvate complexes [M = Mn(II), Co(II), Ni(II) or Zn(II)] were crystallized from acetonitrile and/or methanol solutions. The crystal structures are compared to those of the analogous, isostructural copper compounds (X = Cl or Br) reported earlier. The complexes crystallize in the monoclinic space group P21/n with Z = 4, and unit cell dimensions of a ≈ 14.1, b ≈ 16.1, c ≈ 15.7 °A and β ≈ 108 - 109°. The asymmetric unit of these compounds contains one MCl42− anion, two Bz2Me2N+ cations in theW-conformation and one half of a disordered solvent molecule (acetonitrile or methanol). The geometry of the MCl42− anion is close to tetrahedral, whereas the analogous copper anions appeared in distorted tetrahedral geometries with trans angles of 124.4° for X = Cl and 123.6° for X = Br. In addition to the ionic interactions between the cations and the anions, the components are connected by weak C-H· · · Cl− bonds. As a distinction between the two crystallographically independent cations in the asymmetric unit, one type of independent cations form long chains via weak edge to face π-π interactions along the crystallographic b axis, whereas the other type of cations are not tied together by such weak π-π interactions. The coordination around the N atoms is also nearly tetrahedral, and neither static nor dynamic disorder of the Bz2Me2N+ cations can be observed. The complexes are thermally stable and melt close to the decomposition temperatures in the range 170 - 205 °C.

Basic halides and related species of molybdenum(III). I. The empirical formulae and unit cell dimensions of the basic halides

1976 ◽  
Vol 29 (4) ◽  
pp. 711 ◽  
Author(s):  
DJ Stabb
Keyword(s):  
Evolved Gas Analysis ◽  
Gas Analysis ◽  
Unit Cell ◽  
Water Molecules ◽  
Orthorhombic Unit Cell ◽  
Evolved Gas ◽  
X Ray ◽  
Cell Parameters ◽  
Cell Dimensions ◽  
Unit Cell Dimensions

The basic halides MoOX(H2O), (X = F, Cl) were examined by vacuogravimetric and evolved gas analysis and by X-ray and electron diffraction techniques. The basic chloride prepared by slow crystallization had y = 3.08, with an orthorhombic unit cell 0.723 by 0.820 by 1.805 nm. Basic chlorides produced by rapid precipitation were less crystalline, of slightly larger unit cell dimensions and had 3.0 < y < 4.3. The water in excess of y = 3 was loosely held, while three water molecules per molybdenum were more strongly held. The fluoride, which could not be obtained with the perfect MoOF(H2O)3 stoichiometry, was isomorphous (cell parameters 0.710 by 0.823 by 1.824 nm for [MoOF0.96(OH)0.04(H2O)3] (H2O)0.28). It is concluded that the only hydrate of MoOX existing under normal conditions is MoOX(H2O)3, not the previously reported tetrahydrate.

scholarly journals Simulation of electron density maps for two-dimensional crystal structures usingMathematica

2001 ◽  
Vol 34 (5) ◽  
pp. 658-660 ◽  
Author(s):  
Plinio Delatorre ◽  
Walter Filgueira de Azevedo Jr
Keyword(s):  
Crystal Structures ◽  
Electron Density ◽  
Two Dimensional ◽  
Thermal Displacement ◽  
Density Maps ◽  
Cell Dimensions ◽  
Unit Cell Dimensions ◽  
The Relationship ◽  
Dimensional Crystal

The simulations presented here are based on the programMathematicaas a tool to present electron density maps of two-dimensional crystal structures. The models give further insights into the relationship between the thermal displacement parameters and the quality of the electron density maps. Furthermore, users can readily test the effects of several crystallographic parameters on the electron density maps, such as, the number of reflections, the thermal displacement parameters and the unit-cell dimensions.

Cyclometallation Reactions. XXI. Some Chemistry of Binuclear Manganese Complexes Derived From Azobenzene: X-Ray Crystal-Structures of {Mn (CO)4}2(μ- C6H4N=NC6H4) and {Mn (CO)4}{ Mn (CO)3[P(OPh)3]}(μ-C6H4N=NC6H4)

1988 ◽  
Vol 41 (9) ◽  
pp. 1407 ◽  
Author(s):  
MI Bruce ◽  
MJ Liddell ◽  
MR Snow ◽  
ERT Tiekink
Keyword(s):  
Crystal Structures ◽  
Binuclear Complex ◽  
Hydrogen Transfer ◽  
Monoclinic Space Group ◽  
Subsequent Reaction ◽  
Triclinic Space Group ◽  
Space Group ◽  
X Ray ◽  
Cell Dimensions ◽  
Unit Cell Dimensions

The reaction between azobenzene and Mn (CH2Ph)(CO)5, carried out in refluxing n-octane, afforded the binuclear complex {Mn (CO)4}2(μ- C6H4N=NC6H4) (2) as the first isolable product; subsequent reaction with azobenzene gave Mn (C6H4N= NPh )(CO)4. With P( OPh )3, the binuclear complex undergoes CO substitution but not hydrogen transfer, to give {Mn (CO)4}{ Mn (CO)3[P(OPh)3]}(μ-C6H4N=NC6H4)(3). The X-ray crystal structures of the title complexes have been determined. Compound (2) crystallizes in the monoclinic space group P21/c with unit cell dimensions a 10.161(2), b 23.586(4), c 13.091(4)Ǻ, β 97.10(2)° with Z = 6; crystals of (3) are triclinic, space group Pī , a 12.886(3), b 13.920(3), c 10.428(7)Ǻ, α 97.11(4),β 102.60(4), γ 81.78(2)°. The structures were refined by a full-matrix least-squares procedure to final R 0.041 and Rw 0.048 for 3459 reflections with I ≥ 2.5σ(I) for (2), and R 0.095 and Rw 0.106 for 3406 reflections for (3).

Structures of three inclusion compounds of cholanamide with either (S)-enantiomer, (R)-enantiomer or an optically resolved mixture of butan-2-ol

1996 ◽  
Vol 52 (4) ◽  
pp. 728-733 ◽  
Author(s):  
P. Briozzo ◽  
T. Kondo ◽  
K. Sada ◽  
M. Miyata ◽  
K. Miki
Keyword(s):  
Crystal Structures ◽  
Inclusion Compounds ◽  
Unit Cell Volume ◽  
Optical Resolution ◽  
Unit Cell ◽  
Molar Ratio ◽  
Hydrogen Bond Network ◽  
Cell Dimensions ◽  
Bond Network ◽  
Unit Cell Dimensions

The three types of inclusion compounds of cholanamide (CAM, 3α, 7α, 12α-trihydroxy-5β-cholan-24-amide) have been crystallized from the solutions of (S)-butan-2-ol (CAMSB), (R)-butan-2-ol (CAMRB) and racemic butan-2-ol (CAMSRB), respectively. The crystal structures have been determined. The three crystal structures are isomorphous to each other and revealed that the host CAM molecules form the same layered arrangements, providing channel spaces for the guest butan-2-ol molecules. As expected, the CAMSB and CAMRB crystals include the pure (S)- and (R)-enantiomers of butan-2-ol, whereas the (S)-enriched mixture of enantiomers is accommodated in CAMSRB with a molar ratio between the host CAM and guest butan-2-ol molecules of 1:1. The hydrogen-bond network is rigidly formed between the CAM molecules and also between CAM and butan-2-ol molecules. CAMSB and CAMRB have slightly different unit-cell dimensions: the channels in CAMRB have a larger section, resulting in a larger unit-cell volume. In CAMSRB, although both enantiomers of the guest alcohol are included, the (S)-enantiomer is more abundant, indicating that the optical resolution occurs during the crystallization step.

Bettertonite, [Al6(AsO4)3(OH)9(H2O)5]·11H2O, a new mineral from the Penberthy Croft mine, St. Hilary, Cornwall, UK, with a structure based on polyoxometalate clusters

2015 ◽  
Vol 79 (7) ◽  
pp. 1849-1858 ◽  
Author(s):  
I.E. Grey ◽  
A.R. Kampf ◽  
J.R. Price ◽  
C.M. Macrae
Keyword(s):  
Layer Structure ◽  
New Mineral ◽  
Water Molecules ◽  
Monoclinic Space Group ◽  
X Ray Diffraction ◽  
Calculated Density ◽  
Hexagonal Ring ◽  
Metal Atoms ◽  
Cell Dimensions ◽  
Unit Cell Dimensions

AbstractBettertonite, ideally [Al6(AsO4)3(OH)9(H2O)5]·11H2O, is a new mineral from the Penberthy Croft mine, St. Hilary, Cornwall, England, UK. It occurs as tufts of white, ultrathin (sub-micrometre) rectangular laths, with lateral dimensions generally <20 μm. The laths are flattened on {010} and exhibit the forms {010}, {100} and {001}. The mineral is associated closely with arsenopyrite, chamosite, liskeardite, pharmacoalumite, pharmacosiderite and quartz. Bettertonite is translucent with a white streak and a vitreous to pearly, somewhat silky lustre. The calculated density is 2.02 g/cm3. Optically, bettertonite is biaxial positive with α = 1.511(1), β = 1.517(1), γ = 1.523(1) (in white light). The optical orientation is X = c, Y= b, Z = a. Pleochroism was not observed. Electron microprobe analyses (average of 4) with H2O calculated on structural grounds and analyses normalized to 100% gave Al2O3 = 29.5, Fe2O3 = 2.0, As2O5= 30.1, SO3 = 1.8, Cl = 0.5, H2O = 36.2. The empirical formula, based on 9 metal atoms is Al5.86Fe0.26(AsO4)2.65(SO4)0.23(OH)9.82Cl0.13(H2O)15.5. Bettertoniteis monoclinic, space group P21/c with unit-cell dimensions (100 K): a = 7.773(2), b = 26.991(5), c = 15.867(3) Å, β = 94.22(3)°. The strongest lines in the powder X-ray diffraction pattern are [dobs in Å(I)(hkl)] 13.648(100)(011); 13.505(50) (020); 7.805(50)(031); 7.461(30)(110); 5.880(20)(130); 3.589(20)(02); 2.857(14)(182). The structure of bettertonite was solved and refined to R1 = 0.083 for 2164 observed (I > 2σ(I)) reflections to a resolutionof 1 Å. Bettertonite has a heteropolyhedral layer structure, with the layers parallel to (010). The layers are strongly undulating and their stacking produces large channels along [100] that are filled with water molecules. The basic building block in the layers is a hexagonal ring ofedge-shared octahedra with an AsO4 tetrahedron attached to one side of the ring by corner-sharing. These polyoxometalate clusters, of composition [AsAl6O11(OH)9(H2O)5]8–, are interconnected along [100] and [001]by corner-sharing with other AsO4 tetrahedra.

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