scholarly journals Crystal structures ofN-[(4-phenylthiazol-2-yl)carbamothioyl]benzamide andN-{[4-(4-bromophenyl)thiazol-2-yl]carbamothioyl}benzamide from synchrotron X-ray diffraction

2016 ◽  
Vol 72 (9) ◽  
pp. 1343-1347 ◽  
Author(s):  
Ekaterina S. Gantimurova ◽  
Alexander S. Bunev ◽  
Kristina Yu. Talina ◽  
Gennady I. Ostapenko ◽  
Pavel V. Dorovatovskii ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Dihedral Angles ◽  
Active Pharmaceutical Ingredients ◽  
X Ray Diffraction ◽  
Compound I ◽  
X Ray ◽  
Pharmaceutical Ingredients ◽  
Phenyl Rings ◽  
Compound Ii

The title compounds, C17H13N3OS2, (I), and C17H12BrN3OS2, (II), are potential active pharmaceutical ingredients. Compound (I) comprises two almost planar fragments. The first is the central (carbamothioyl)amide (r.m.s. deviation = 0.038 Å), and the second consists of the thiazole and two phenyl rings (r.m.s. deviation = 0.053 Å). The dihedral angle between these planes is 15.17 (5)°. Unlike (I), compound (II) comprises three almost planar fragments. The first is the centralN-(thiazol-2-ylcarbamothioyl)amide (r.m.s. deviation = 0.084 Å), and the two others comprise the bromophenyl and phenyl substituents, respectively. The dihedral angles between the central and two terminal planar fragments are 21.58 (7) and 17.90 (9)°, respectively. Both (I) and (II) feature an intramolecular N—H...O hydrogen bond, which closes anS(6) ring. In the crystal of (I), molecules form hydrogen-bonded layers parallel to (100) mediated by N—H...S and C—H...O hydrogen bonds. In the crystal of (II), molecules form a three-dimensional framework mediated by N—H...Br and C—H...O hydrogen bonds, as well as secondary S...Br [3.3507 (11) Å] and S...S [3.4343 (14) Å] interactions.

scholarly journals Crystal structures of two new carbazole derivatives: 12-(4-nitrophenyl)-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole and 2-methyl-4-(4-nitrophenyl)-9-phenylsulfonyl-9H-thieno[2,3-b]carbazole

2016 ◽  
Vol 72 (12) ◽  
pp. 1739-1743
Author(s):  
K. Swaminathan ◽  
P. Narayanan ◽  
K. Sethusankar ◽  
Velu Saravanan ◽  
Arasambattu K. Mohanakrishnan
Keyword(s):  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Ring System ◽  
Molecular Structures ◽  
Dihedral Angles ◽  
Compound I ◽  
Carbazole Derivatives ◽  
Phenyl Rings ◽  
The Mean ◽  
Compound Ii

The title compounds, C30H18N2O5S, (I), and C27H18N2O4S2, (II), are carbazole derivatives with a phenylsulfonyl group and a nitrophenyl group attached to the carbazole moiety in identical positions in both molecules. A benzofuran ring system in (I) and a methylthiophene ring in (II) are fused with the respective carbazole moieties on the same sides. The mean plane of the carbazole ring system makes a dihedral angle of 3.17 (7)° with the benzofuran ring system in (I) and a dihedral angle of 3.39 (11)° with the methylthiophene ring in (II), implying that both fused units are essentially planar. The mean planes of the carbazole ring systems in both the compounds are almost orthogonal to the respective nitro-substituted phenyl rings, making dihedral angles of 75.64 (10) and 77.63 (12)° in compounds (I) and (II), respectively. In (I), the phenylsulfonyl ring system is positionally disordered with a refined occupancy ratio of 0.63 (2):0.37 (2). In both compounds, the molecular structures are stabilized by intramolecular C—H...O hydrogen bonds, generatingS(6) ring motifs with the sulfone group O atoms. In the crystal of compound (I), molecules are linked by pairs of C—H...O hydrogen bonds, which generateR22(18) inversion dimers, and interconnected byC(14) chains running along thec-axis direction, whereas in compound (II), the C—H...O hydrogen bonds generateR43(37) ring motifs. In the crystals of both compounds, C—H...O hydrogen-bonded sheets are formed lying parallel to (10-1). In addition, C—H...π and offset π–π interactions [intercentroid distance = 3.7158 (14) Å in (I) and 3.9040 (15) Å in (II)] are also present in the crystals of both compounds.

scholarly journals Isotypic crystal structures of 2,6-dibromo-N,N-bis(4-nitrophenyl)aniline and 2,6-dichloro-N,N-bis(4-nitrophenyl)aniline

2014 ◽  
Vol 70 (8) ◽  
pp. 65-67 ◽  
Author(s):  
Paul Kautny ◽  
Johannes Fröhlich ◽  
Berthold Stöger ◽  
Matthias Weil
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Van Der Waals ◽  
Three Dimensional ◽  
Compound I ◽  
Dimensional Network ◽  
Phenyl Rings ◽  
The Mean ◽  
Compound Ii ◽  
Van Der Waals Radii

In the molecules of the two isotypic title compounds, C18H11Br2N3O4(I) and C18H11Cl2N3O4(II), the triphenylamine N atoms show no sign of pyramidalization, with marginal displacements of the N atoms from the mean plane of the three connecting C atoms: 0.0058 (13) Å for the Br compound (I) and 0.0074 (9) Å for the Cl compound (II). In the crystals, molecules are linked through C—H...O hydrogen bonds between phenyl rings and nitro groups and byX...O (X= Br, Cl) interactions, that are shorter than the sum of the van der Waals radii, leading to a three-dimensional network.

scholarly journals Crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1H-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1H-indole

2017 ◽  
Vol 73 (10) ◽  
pp. 1555-1559
Author(s):  
G. Dhanalakshmi ◽  
Velu Saravanan ◽  
Arasambattu K. Mohanakrishnan ◽  
S. Aravindhan
Keyword(s):  
Hydrogen Bonds ◽  
Ring System ◽  
Dihedral Angles ◽  
Indole Derivatives ◽  
Indole Ring ◽  
Compound I ◽  
Tetrahedral Geometry ◽  
Distorted Tetrahedral Geometry ◽  
Phenyl Rings ◽  
Compound Ii

In the title indole derivatives, C22H16N2O5S, (I) and C20H15NO3S2, (II), the sulfonyl-bound phenyl rings are almost orthogonal to the indole ring system, subtending dihedral angles of 88.33 (10) and 87.58 (16)°, respectively. In both compounds, the sulfonyl S atom has a distorted tetrahedral geometry [O—S—O = 119.98 (9) and N—S—C = 104.01 (8)° for compound (I) and O—S—O = 120.08 (18) and N—S—C = 104.91 (14)° for compound (II)] and the sum of the bond angles at N indicatessp2hybridization. The molecules of both (I) and (II) feature intramolecular C—H...O hydrogen bonds that generateS(6) ring motifs with the sulfone O atom. In the crystals, molecules of (I) are linked by C—H—O hydrogen bonds, formingR44(18) ring motifs while molecules of (II) are linked by C—H—O and C—H—S hydrogen bonds, formingR22(12) ring motifs. Compound (II) was refined as an inversion twin.

One-pot concomitant preparation of two copper(II) coordination polymers with different configurations of bridging bithiophene ligands

2020 ◽  
Vol 76 (1) ◽  
pp. 37-43
Author(s):  
Zhi-Qiang Shi ◽  
Ning-Ning Ji ◽  
Hai-Liang Hu
Keyword(s):  
Hydrogen Bonds ◽  
Single Crystal ◽  
Coordination Polymers ◽  
Three Dimensional ◽  
Chain Structure ◽  
X Ray Diffraction ◽  
Compound I ◽  
One Pot ◽  
X Ray ◽  
Vis Spectroscopy

By employing the conjugated bithiophene ligand 5,5′-bis(1H-imidazol-1-yl)-2,2′-bithiophene (bibp), which can exhibit trans and cis conformations, two different CuII coordination polymers, namely, poly[[μ-5,5′-bis(1H-imidazol-1-yl)-2,2′-bithiophene-κ2 N:N′](μ2-4,4′-oxydibenzoato-κ2 O:O′)copper(II)], [Cu(C14H8O5)(C14H10N4S2)] n or [Cu(bibp)(oba)] n , (I), and catena-poly[μ-aqua-bis[μ-5,5′-bis(1H-imidazol-1-yl)-2,2′-bithiophene-κ2 N:N′]bis(μ3-4,4′-oxydibenzoato)-κ3 O:O′:O′′;κ4 O:O′,O′′:O′-dicopper(II)], [Cu2(C14H8O5)2(C14H10N4S2)(H2O)] n or [Cu2(bibp)(oba)2(H2O)] n , (II), have been prepared through one-pot concomitant crystallization and characterized by single-crystal X-ray diffraction, IR spectroscopy, elemental analysis, powder X-ray diffraction (PXRD) and thermogravimetric (TG) analysis. Single-crystal X-ray diffraction indicates that the most interesting aspect of the structure is the existence of sole trans and cis conformations of the bibp ligand in a single net of (I) and (II), respectively. Compound (I) displays a threefold interpenetrating three-dimensional framework with a 4-connected {65.8} cds topology, whereas (II) features a one-dimensional chain structure. In the crystal of (II), the polymeric chains are further extended through C—H...O hydrogen bonds and C—H...π interactions into a three-dimensional supramolecular architecture. In addition, strong intramolecular O—H...O hydrogen bonds formed between the bridging water molecules and the carboxylate O atoms improve the stability of the framework of (II). Furthermore, solid-state UV–Vis spectroscopy experiments show that compounds (I) and (II) exhibit optical band gaps which are characteristic for optical semiconductors, with values of 2.70 and 2.26 eV, respectively.

scholarly journals Syntheses and crystal structures of two adamantyl-substituted 1,2,4-triazole-5-thione N-Mannich bases

2017 ◽  
Vol 73 (8) ◽  
pp. 1135-1139 ◽  
Author(s):  
Monirah A. Al-Alshaikh ◽  
Aamal A. Al-Mutairi ◽  
Hazem A. Ghabbour ◽  
Ali A. El-Emam ◽  
Mohammed S. M. Abdelbaky ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Phenyl Ring ◽  
Triazole Ring ◽  
Mannich Bases ◽  
Dihedral Angles ◽  
Compound I ◽  
Piperazine Ring ◽  
Phenyl Rings ◽  
Compound Ii

In the title N-Mannich bases, 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1-[(4-phenylpiperazin-1-yl)methyl]-4,5-dihydro-1H-1,2,4-triazole-5-thione (C29H34FN5S) (I), and 3-(adamantan-1-yl)-4-(4-fluorophenyl)-1-{[4-(2-methoxyphenyl)piperazin-1-yl]-methyl}-4,5-dihydro-1H-1,2,4-triazole-5-thione (C30H36FN5OS) (II), fluorophenyl, adamantane and piperazine moieties are linked to a planar triazole ring. There is an additional phenyl ring on the piperazine ring in (I) and a methoxyphenyl ring in (II). In compound (I), the fluorophenyl and phenyl rings are inclined to the triazole ring by 86.55 (13) and 60.52 (12)°, respectively, and the two aryl rings are inclined to one another by 66.37 (13)°. In compound (II), the corresponding dihedral angles are 83.35 (13), 71.38 (15) and 11.97 (16)°, respectively. The crystal structure of (I) shows pairs of C—H...F hydrogen bonds forming inversion dimers, while in the crystal of compound (II), in addition to the C—H...F hydrogen bonds that generate chains parallel to the b axis, there are C—H...π interactions present that link the chains to form layers parallel to the ab plane.

scholarly journals Acemetacin cocrystals and salts: structure solution from powder X-ray data and form selection of the piperazine salt

IUCrJ ◽  
2014 ◽  
Vol 1 (2) ◽  
pp. 136-150 ◽  
Author(s):  
Palash Sanphui ◽  
Geetha Bolla ◽  
Ashwini Nangia ◽  
Vladimir Chernyshev
Keyword(s):  
Hydrogen Bonds ◽  
Dissolution Rate ◽  
Aqueous Medium ◽  
Acid Amide ◽  
Three Dimensional ◽  
X Ray Diffraction ◽  
Reference Drug ◽  
X Ray ◽  
Time Period ◽  
Solid Form

Acemetacin (ACM) is a non-steroidal anti-inflammatory drug (NSAID), which causes reduced gastric damage compared with indomethacin. However, acemetacin has a tendency to form a less soluble hydrate in the aqueous medium. We noted difficulties in the preparation of cocrystals and salts of acemetacin by mechanochemical methods, because this drug tends to form a hydrate during any kind of solution-based processing. With the objective to discover a solid form of acemetacin that is stable in the aqueous medium, binary adducts were prepared by the melt method to avoid hydration. The coformers/salt formers reported are pyridine carboxamides [nicotinamide (NAM), isonicotinamide (INA), and picolinamide (PAM)], caprolactam (CPR),p-aminobenzoic acid (PABA), and piperazine (PPZ). The structures of an ACM–INA cocrystal and a binary adduct ACM–PABA were solved using single-crystal X-ray diffraction. Other ACM cocrystals, ACM–PAM and ACM–CPR, and the piperazine salt ACM–PPZ were solved from high-resolution powder X-ray diffraction data. The ACM–INA cocrystal is sustained by the acid...pyridine heterosynthon and N—H...O catemer hydrogen bonds involving the amide group. The acid...amide heterosynthon is present in the ACM–PAM cocrystal, while ACM–CPR contains carboxamide dimers of caprolactam along with acid–carbonyl (ACM) hydrogen bonds. The cocrystals ACM–INA, ACM–PAM and ACM–CPR are three-dimensional isostructural. The carboxyl...carboxyl synthon in ACM–PABA posed difficulty in assigning the position of the H atom, which may indicate proton disorder. In terms of stability, the salts were found to be relatively stable in pH 7 buffer medium over 24 h, but the cocrystals dissociated to give ACM hydrate during the same time period. The ACM–PPZ salt and ACM–nicotinamide cocrystal dissolve five times faster than the stable hydrate form, whereas the ACM–PABA adduct has 2.5 times faster dissolution rate. The pharmaceutically acceptable piperazine salt of acemetacin exhibits superior stability, faster dissolution rate and is able to overcome the hydration tendency of the reference drug.

scholarly journals Crystal structures of {[Cu(Lpn)2][Fe(CN)5(NO)]·H2O}nand {[Cu(Lpn)2]3[Cr(CN)6]2·5H2O}n[where Lpn = (R)-propane-1,2-diamine]: two heterometallic chiral cyanide-bridged coordination polymers

2015 ◽  
Vol 71 (4) ◽  
pp. 392-397
Author(s):  
Olha Sereda ◽  
Helen Stoeckli-Evans
Keyword(s):  
Hydrogen Bonds ◽  
Coordination Polymers ◽  
Three Dimensional ◽  
Water Molecules ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Compound I ◽  
Distorted Octahedral ◽  
Coordination Spheres ◽  
Compound Ii

The title compounds,catena-poly[[[bis[(R)-propane-1,2-diamine-κ2N,N′]copper(II)]-μ-cyanido-κ2N:C-[tris(cyanido-κC)(nitroso-κN)iron(III)]-μ-cyanido-κ2C:N] monohydrate], {[Cu(Lpn)2][Fe(CN)5(NO)]·H2O}n, (I), and poly[[hexa-μ-cyanido-κ12C:N-hexacyanido-κ6C-hexakis[(R)-propane-1,2-diamine-κ2N,N′]dichromium(III)tricopper(II)] pentahydrate], {[Cu(Lpn)2]3[Cr(CN)6]2·5H2O}n, (II) [where Lpn = (R)-propane-1,2-diamine, C3H10N2], are new chiral cyanide-bridged bimetallic coordination polymers. The asymmetric unit of compound (I) is composed of two independent cation–anion units of {[Cu(Lpn)2][Fe(CN)5)(NO)]} and two water molecules. The FeIIIatoms have distorted octahedral geometries, while the CuIIatoms can be considered to be pentacoordinate. In the crystal, however, the units align to form zigzag cyanide-bridged chains propagating along [101]. Hence, the CuIIatoms have distorted octahedral coordination spheres with extremely long semicoordination Cu—N(cyanido) bridging bonds. The chains are linked by O—H...N and N—H...N hydrogen bonds, forming two-dimensional networks parallel to (010), and the networks are linkedviaN—H...O and N—H...N hydrogen bonds, forming a three-dimensional framework. Compound (II) is a two-dimensional cyanide-bridged coordination polymer. The asymmetric unit is composed of two chiral {[Cu(Lpn)2][Cr(CN)6]}−anions bridged by a chiral [Cu(Lpn)2]2+cation and five water molecules of crystallization. Both the CrIIIatoms and the central CuIIatom have distorted octahedral geometries. The coordination spheres of the outer CuIIatoms of the asymmetric unit can be considered to be pentacoordinate. In the crystal, these units are bridged by long semicoordination Cu—N(cyanide) bridging bonds forming a two-dimensional network, hence these CuIIatoms now have distorted octahedral geometries. The networks, which lie parallel to (10-1), are linkedviaO—H...O, O—H...N, N—H...O and N—H...N hydrogen bonds involving all five non-coordinating water molecules, the cyanide N atoms and the NH2groups of the Lpn ligands, forming a three-dimensional framework.

scholarly journals 4-Fluoro-N-(4-hydroxybenzylidene)aniline

2014 ◽  
Vol 70 (8) ◽  
pp. o860-o860
Author(s):  
L. Jothi ◽  
G. Anuradha ◽  
G. Vasuki ◽  
R. Ramesh Babu ◽  
K. Ramamurthi
Keyword(s):  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Schiff Bases ◽  
Title Compound ◽  
Three Dimensional ◽  
Dihedral Angles ◽  
Axis Direction ◽  
Compound C ◽  
Dimensional Network ◽  
Phenyl Rings

In the title compound, C13H10FNO, the benzene ring planes are inclined at an angle of 50.52 (8)°. A characteristic of aromatic Schiff bases withN-aryl substituents is that the terminal phenyl rings are twisted relative to the plane of the HC=N link between them. In this case, the HC=N unit makes dihedral angles of 10.6 (2) and 40.5 (2)° with the hydroxybenzene and flurobenzene rings, respectively. In the crystal, O—H...N and C—H...F hydrogen bonds lead to the formation of chains along thec-andb-axis directions, respectively. C—H...π contacts link molecules alongaand these contacts combine to generate a three-dimensional network with molecules stacked along theb-axis direction.

scholarly journals Crystal structure of (E)-N-{2-[2-(4-methylbenzylidene)hydrazin-1-yl]-2-oxoethyl}-p-toluenesulfonamide

2015 ◽  
Vol 71 (6) ◽  
pp. 730-733 ◽  
Author(s):  
H. Purandara ◽  
Sabine Foro ◽  
B. Thimme Gowda
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Dihedral Angles ◽  
Asymmetric Unit ◽  
Acid Moiety ◽  
Torsion Angles ◽  
Centroid Distance ◽  
Benzene Rings ◽  
Amino Acid Moiety ◽  
Phenyl Rings

The title acylhydrazone derivative, C17H19N3O3S, containing an amino acid moiety and electron-donating substituents attached to both the phenyl rings, crystallized with two independent molecules (AandB) in the asymmetric unit. The molecules are bent at the S atom, with C—SO2—NH—CH2torsion angles of −67.3 (2) and 67.7 (3)° in moleculesAandB, respectively. Further, the dihedral angles between the sulfonylglycine segments and thep-toluenesulfonyl rings are 76.1 (1) and 85.8 (1)° in moleculesAandB, respectively. The central hydrazone segments and the toluene rings attached to them are almost co-planar with their mean planes being inclined to one another by 5.2 (2) (moleculeA) and 2.9 (2)° (moleculeB). The dihedral angles between the benzene rings are 86.83 (12) (moleculeA) and 74.00 (14)° (moleculeB). In the crystal, theAmolecules are linked by a pair of N—H...O hydrogen bonds, forming inversion dimers with anR22(8) ring motif. The dimers are linkedviathree N—H...O hydrogen bonds involving theBmolecules, forming chains along [100] and enclosingR22(12) andR44(16) ring motifs. The chains are linkedviaC—H...O hydrogen bonds and a C—H...π interaction, forming sheets parallel to (010). There is a further C—H...π interaction and a slipped parallel π–π interaction [inter-centroid distance = 3.8773 (16) Å] between the sheets, leading to the formation of a three-dimensional framework.

scholarly journals Assay and physicochemical characterization of the antiparasitic albendazole

2012 ◽  
Vol 48 (2) ◽  
pp. 281-290 ◽  
Author(s):  
Noely Camila Tavares Cavalcanti ◽  
Giovana Damasceno Sousa ◽  
Maria Alice Maciel Tabosa ◽  
José Lamartine Soares Sobrinho ◽  
Leila Bastos Leal ◽  
...  
Keyword(s):  
Physicochemical Characterization ◽  
Analytical Techniques ◽  
Assay Method ◽  
Active Pharmaceutical Ingredients ◽  
X Ray Diffraction ◽  
Melting Points ◽  
X Ray ◽  
Pharmaceutical Ingredients ◽  
Complementary Techniques

The aim of this study was to characterize three batches of albendazole by pharmacopeial and complementary analytical techniques in order to establish more detailed specifications for the development of pharmaceutical forms. The ABZ01, ABZ02, and ABZ03 batches had melting points of 208 ºC, 208 ºC, and 209 ºC, respectively. X-ray diffraction revealed that all three batches showed crystalline behavior and the absence of polymorphism. Scanning electron microscopy showed that all the samples were crystals of different sizes with a strong tendency to aggregate. The samples were insoluble in water (5.07, 4.27, and 4.52 mg mL-1, respectively) and very slightly soluble in 0.1 M HCl (55.10, 56.90, and 61.70 mg mL-1, respectively) and additionally showed purities within the range specified by the Brazilian Pharmacopoeia 5th edition (F. Bras. V; 98% to 102%). The pharmacopeial assay method was not reproducible and some changes were necessary. The method was validated and showed to be selective, specific, linear, robust, precise, and accurate. From this characterization, we concluded that pharmacopeial techniques alone are not able to detect subtle differences in active pharmaceutical ingredients; therefore, the use of other complementary techniques is required to ensure strict quality control in the pharmaceutical industry.

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