Racemic -bis-[bis-(pyrimidin-2-yl)amine-κ]bis(dicyanamido-κ)iron(II) dihydrate: synthesis, crystal structure and Hirshfeld surface analysis.

The title compound, [Fe(CN)(CHN)]·2HO, has been synthesized solvothermally and characterized by single-crystal X-ray diffraction. The octa-hedral iron coordination polyhedron contains two di(pyrimidin-2-yl)amine ligands coordinated in a bidentate fashion, and two monodentate dicyanimido ligands, each coordinated a terminal N atom, with the latter in a orientation. The ligand configuration about the iron atom is chiral, although the compound crystallizes as a racemic mixture: the Fe-N distances (> 2.

Synthesis of 5-(arylmethylideneamino)-4-(1H-benzo[d]imidazol-1-yl)pyrimidine hybrids: synthetic sequence and the molecular and supramolecular structures of two intermediates and three final products.

A concise and versatile synthesis of 5-(arylmethylideneamino)-4-(1H-benzo[d]imidazol-1-yl)pyrimidines has been developed, starting from 4-(1H-benzo[d]imidazol-1-yl)pyrimidines, and we report here the synthesis and spectroscopic and structural characterization of three such products, along with those of two intermediates in the reaction pathway. The intermediates 4-[2-(4-chlorophenyl)-1H-benzo[d]imidazol-1-yl]-6-methoxypyrimidine-2,5-diamine, (II), and 4-[2-(4-bromophenyl)-1H-benzo[d]imidazol-1-yl]-6-methoxypyrimidine-2,5-diamine, (III), crystallize as the isostructural monohydrates CHClNO·HO and CHBrNO·HO, respectively, in which the components are linked into complex sheets by O-H..

Conversion of 2-methyl-4-styrylquinolines into 2,4-distyrylquinolines: synthesis, and spectroscopic and structural characterization of five examples.

Four new 2,4-distyrylquinolines and one 2-styryl-4-[2-(thiophen-2-yl)vinyl]quinoline have been synthesized using indium trichloride condensation reactions between aromatic aldehydes and the corresponding 2-methylquinolines, which were themselves prepared using Friedländer annulation reactions between mono- or diketones and (2-aminophenyl)chalcones: the products have all been fully characterized by spectroscopic and crystallographic methods. 2,4-Bis[(E)-styryl]quinoline, CHN, (IIa), and its dichloro analogue, 2-[(E)-2,4-dichlorostyryl]-4-[(E)-styryl]quinoline, CHClN, (IIb), exhibit different orientations of the 2-styryl unit relative to the quinoline nucleus. In each of the 3-benzoyl analogues {2-[(E)-4-bromostyryl]-4-[(E)-styryl]quinolin-3-yl}(phenyl)methanone, CHBrNO, (IIc), {2-[(E)-4-bromostyryl]-4-[(E)-4-chlorostyryl]quinolin-3-yl}(phenyl)methanone, CHBrClNO, (IId), and {2-[(E)-4-bromostyryl]-4-[(E)-2-(thiophen-2-yl)vinyl]quinolin-3-yl}(phenyl)methanone, CHBrNOS, (IIe), the orientation of the 2-styryl unit is similar to that in (IIa), but the orientation of the 4-arylvinyl units show considerable variation.

(E,E)-1,1'-[1,2-Bis(4-chlorophenyl)ethane-1,2-diyl]bis(phenyldiazene) revisited: threefold configurational disorder of (S,S), (R,R) and (S,R) isomers, a detailed critique.

Crystal structures described as concomitant triclinic (I) and monoclinic (II) polymorphs of meso-(E,E)-1,1'-[1,2-bis(4-chlorophenyl)ethane-1,2-diyl]bis(phenyldiazene) [Mohamed et al. (2016). Acta Cryst.

A three-step pathway from (2-aminophenyl)chalcones to novel styrylquinoline-chalcone hybrids: synthesis and spectroscopic and structural characterization of three examples.

Three new styrylquinoline-chalcone hybrids have been synthesized using a three-step pathway starting with Friedländer cyclocondensation between (2-aminophenyl)chalcones and acetone to give 2-methyl-4-styrylquinolines, followed by selective oxidation to the 2-formyl analogues, and finally Claisen-Schmidt condensation between the formyl intermediates and 1-acetylnaphthalene. All intermediates and the final products have been fully characterized by IR and H/C NMR spectroscopy, and by high-resolution mass spectrometry, and the three products have been characterized by single-crystal X-ray diffraction. The molecular conformations of (E)-3-{4-[(E)-2-phenylethenyl]quinolin-2-yl}-1-(naphthalen-1-yl)prop-2-en-1-one, CHNO, (IVa), and (E)-3-{4-[(E)-2-(4-fluorophenyl)ethenyl]quinolin-2-yl}-1-(naphthalen-1-yl)prop-2-en-1-one, CHFNO, (IVb), are very similar.

Synthesis, and spectroscopic and structural characterization of three new styrylquinoline-benzimidazole hybrids.

Three new 4-styrylquinoline-benzimidazole hybrids have been synthesized using a reaction sequence in which 2-methylquinoline precursors first undergo selective oxidation by selenium dioxide to form the corresponding 2-formylquinoline intermediates, followed by oxidative cyclocondensation reactions with benzene-1,2-diamine to yield the hybrid products. The formyl intermediates and the hybrid products have all been fully characterized using a combination of IR, H and C NMR spectroscopy, and high-resolution mass spectrometry, and the structures of the three hybrid products have been determined using single-crystal X-ray diffraction. Ethyl (E)-2-(1H-benzo[d]imidazol-2-yl)-4-(4-chlorostyryl)quinoline-3-carboxylate, CHClNO, (IIIa), and ethyl (E)-2-(1H-benzo[d]imidazol-2-yl)-4-(2-methoxystyryl)quinoline-3-carboxylate, CHNO, (IIIb), both crystallize in the solvent-free form with Z' = 1, but ethyl (E)-2-(1H-benzo[d]imidazol-2-yl)-4-(4-methylstyryl)quinoline-3-carboxylate, CHNO, (IIIc), crystallizes as a partial hexane solvate with Z' = 3, and the ester group in one of the independent molecules is disordered over two sets of atomic sites having occupancies of 0.

Synthesis and crystal structure of topiramate azido-sulfate at 90 K and 298 K.

The low (90 K) and room (298 K) temperature crystal structures of topiramate azido-sulfate [systematic name 2,3:4,5-bis--(1-methyl-ethyl-idene)-β-d-fructo-pyran-ose azido-sulfate], CHNOS, an inter-mediate in the synthesis of the anti-convulsant drug topiramate, are described. Topiramate azido-sulfate () finds use as a reference impurity standard for topiramate. A modified synthesis and some spectroscopic details are also presented.

Synthesis and spectroscopic and structural characterization of three new 2-methyl-4-styrylquinolines formed using Friedländer reactions between (2-aminophenyl)chalcones and acetone.

Three new 2-methyl-4-styrylquinoline derivatives have been synthesized in high yields using Friedländer reactions between chalcones [1-(2-aminophenyl)-3-arylprop-2-en-1-ones] and acetone, and characterized using IR, H and C NMR spectroscopy, and mass spectrometry, and by crystal structure analysis. In (E)-4-(4-fluorostyryl)-2-methylquinoline, CHFN, (I), the molecules are joined into cyclic centrosymmetric dimers by C-H..

Syntheses and crystal structures of 4-(4-meth-oxy-phen-yl)piperazin-1-ium 4-methyl-benzoate monohydrate and bis-[4-(4-meth-oxy-phen-yl)piperazin-1-ium] benzene-1,2-di-carboxyl-ate.

Co-crystallization of -(4-meth-oxy-phen-yl)piperazine with 4-methyl-benzoic acid and with benzene-1,2-di-carb-oxy-lic acid yields the salts 4-(4-meth-oxy-phen-yl)piperazin-1-ium 4-methyl-benzoate monohydrate, CHNO·CHO ·HO (I), and bis-[4-(4-meth-oxy-phen-yl)piperazin-1-ium] benzene-1,2-di-carboxyl-ate, 2CHNO·CHO (II). These salts both crystallize with ' = 2, in space groups and 2, respectively. In compound (I), a combination of four O-H⋯O, four N-H⋯O, one C-H⋯O and one C-H⋯π(arene) hydrogen bonds link the six independent components into complex sheets, within which the two piperazine rings, the two anions, and the two water mol-ecules are related by an approximate, non-crystallographic translation along the -axis direction.

Syntheses and crystal structures of 4-(4-nitro-phen-yl)piperazin-1-ium benzoate monohydrate and 4-(4-nitro-phen-yl)piperazin-1-ium 2-carb-oxy-4,6-di-nitro-phenolate.

Crystal structures are reported for two mol-ecular salts containing the 4-(4-nitro-phen-yl)piperazin-1-ium cation. Co-crystallization from methanol/ethyl acetate solution of -(4-nitro-phen-yl)piperazine with benzoic acid gives the benzoate salt, which crystallizes as a monohydrate, CHNO·CHO·HO, (I), and similar co-crystallization with 3,5-di-nitro-salicylic acid yields the 2-carb-oxy-4,6-di-nitro-phenolate salt, CHNO·CHNO, (II). In the structure of (I), a combination of O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds links the components into sheets, while in the structure of (II), the supra-molecular assembly, generated by hydrogen bonds of the same types as in (I), is three dimensional.

Formation of 1-(thia-zol-2-yl)-4,5-di-hydropyrazoles from simple precursors: synthesis, spectroscopic characterization and the structures of an inter-mediate and two products.

Two new 1-(thia-zol-2-yl)-4,5-di-hydropyrazoles have been synthesized from simple precursors, and characterized both spectroscopically and structurally. In addition, two inter-mediates in the reaction pathway have been isolated and characterized, one of them structurally. The mol-ecules of the inter-mediate ()-1-(4-meth-oxy-phen-yl)-3-[4-(prop-2-yn-yloxy)phen-yl]prop-2-en-1-one, CHO (I), are linked by a combination of C-H⋯O and C-H⋯π(arene) hydrogen bonds to form ribbons.

Synthesis and spectroscopic and structural characterization of spiro[indoline-3,3'-indolizine]s formed by 1,3-dipolar cycloadditions between isatins, pipecolic acid and an electron-deficient alkene.

Five new spiro[indoline-3,3'-indolizine]s have been synthesized with high regio- and stereospecificity in one-pot three-component reactions between a substituted indole-2,3-dione, (S)-pipecolic acid and trans-3-benzoylacrylic acid, and subsequently characterized using a combination of elemental analysis, IR and H and C NMR spectroscopy, mass spectrometry and crystal structure analysis. (1'SR,2'SR,3RS,8a'RS)-2'-Benzoyl-5-fluoro-2-oxo-1',5',6',7',8',8a'-hexahydro-2'H-spiro[indoline-3,3'-indolizine]-1'-carboxylic acid, CHFNO, (I), and (1'SR,2'SR,3RS,8a'RS)-2'-benzoyl-5-methyl-2-oxo-1',5',6',7',8',8a'-hexahydro-2'H-spiro[indoline-3,3'-indolizine]-1'-carboxylic acid, CHNO, (II), are isomorphous, as are (1'SR,2'SR,3RS,8a'RS)-2'-benzoyl-1-methyl-2-oxo-1',5',6',7',8',8a'-hexahydro-2'H-spiro[indoline-3,3'-indolizine]-1'-carboxylic acid, CHNO, (III), and (1'SR,2'SR,3RS,8a'RS)-2'-benzoyl-5-chloro-1-methyl-2-oxo-1',5',6',7',8',8a'-hexahydro-2'H-spiro[indoline-3,3'-indolizine]-1'-carboxylic acid, CHClNO, (IV). Within each isomorphous pair, the spiro ring systems show some conformational differences.

-Poly[[bis-(quinolin-8-amine-κ ,')cadmium(II)]-μ-cyanido-κ :-[dicyanidonickel(II)]-μ-cyanido-κ :].

In the title compound, [CdNi(CHN)(CN)] , the Cd and Ni atoms both lie on centres of inversion in space group 2/. The Cd atom is coordinated by two bidentate quinolin-8-amine ligands and by the N atoms of two cyano ligands, while the square planar Ni atom is coordinated by the C atoms of four cyano ligands. These units form a one-dimensional coordination polymer containing an (-NC-Ni-CN-Cd-) backbone, and the coordination polymer chains are linked into a three-dimensional array by a combination of N-H⋯N and C-H⋯N hydrogen bonds, augmented by a π-π stacking inter-action.

The crystal structures of three disordered 2-substituted benzimidazole esters.

The crystal structures of three benzimidazole esters containing aryl or heterocyclic substituents at position 2 are reported, and all three exhibit disorder of mol-ecular entities. In ethyl 1-methyl-2-[4-(prop-2-yn-oxy)phen-yl]-1-benzimidazole-5-carboxyl-ate, CHNO, (I), the prop-2-yn-1-oxyphenyl unit is disordered over two sets of atomic sites having effectively equal occupancies, 0.506 (5) and 0.

Reduced 3,4'-bi-pyrazoles carrying thio-phene and thia-zole substituents: structures of two intermediates and two products.

Cyclo-addition reactions between 3-(5-ar-yloxy-3-methyl-1-phenyl-1-pyrazol-4-yl)-1-(thio-phen-2-yl)prop-2-en-1-ones and thio-semicarbazide leads to the formation of reduced 3,4'-bi-pyrazole-2-carbo-thio-amides. Further cyclo-addition of these inter-mediates with either diethyl acetyl-enedi-carboxyl-ate or 4-bromo-phenacyl bromide leads to reduced 3,4'-bi-pyrazoles carrying oxo-thia-zole or thia-zole substituents, respectively. The structures of two representative inter-mediates and two representative products established unambiguously the regiochemistry of the cyclo-addition reactions.

Two 3-amino-1-pyrazol-2-ium salts containing organic anions, and an ortho-rhom-bic polymorph of 3-amino-1-pyrazol-2-ium nitrate.

Co-crystallization from methanol of 3-amino-1-pyrazole with 3,5-di-nitro-benzoic acid produces 3-amino-1-pyrazol-2-ium 3,5-di-nitro-benzoate monohydrate, CHN ·CHNO ·HO, (I), while similar co-crystallization of this pyrazole with an equimolar qu-antity of fumaric acid produces bis-(3-amino-1-pyrazol-2-ium) fumarate-fumaric acid (1/1), 2CHN ·CHO ·CHO, (II). The reaction of 3-amino-1-pyrazole with a dilute solution of nitric acid in methanol yields a second, ortho-rhom-bic polymorph of 3-amino-1-pyrazol-2-ium nitrate, CHN ·NO , (III). In each of (I)-(III), the bond distances in the cation provide evidence for extensive delocalization of the positive charge.

Six 1-halobenzoyl-4-(2-meth-oxy-phen-yl)piperazines having ' values of one, two or four; disorder, pseudosymmetry, twinning and supra-molecular assembly in one, two or three dimensions.

Six 1-halobenzoyl-4-(2-meth-oxy-phen-yl)piperazines have been prepared using carbodi-imide-mediated coupling reactions between halo-benzoic acids and -(2-meth-oxy-phen-yl)piperazine. The mol-ecules of 1-(4-fluoro-benzo-yl)-4-(2-meth-oxy-phen-yl)piperazine, CHFNO (I), are linked into a chain of rings by a combination of C-H⋯O and C-H⋯π(arene) hydrogen bonds. 1-(4-Chloro-benzo-yl)-4-(2-meth-oxy-phen-yl)piperazine, CHClNO (II), crystallizes in the space group 2 with ' = 4 and it exhibits both pseudosymmetry and inversion twinning: a combination of six C-H⋯O and two C-H⋯π(arene) hydrogen bonds generate a three-dimensional assembly.

1-(3,5-Di-nitro-benzo-yl)-4-(2-meth-oxy-phen-yl)piper-azine.

In the title compound, CHNO, the piperazine ring adopts a chair conformation, the amidic N atom is planar (sum of angles = 360°) and the non-amidic N atom is pyramidal (343°). There are no hydrogen bonds of any kind in the crystal, but the mol-ecules are linked by two independent π(nitro-benzene)⋯π(meth-oxy-benzene) stacking inter-actions to form π-stacked sheets with inter-centroid separations of 3.8444 (12) and 3.

Fifteen 4-(2-meth-oxy-phen-yl)piperazin-1-ium salts containing organic anions: supra-molecular assembly in zero, one, two and three dimensions.

Fifteen 4-(2-meth-oxy-phen-yl)piperazin-1-ium salts containing organic anions have been prepared and structurally characterized. In the isostructural 4-chloro-benzoate and 4-bromo-benzoate salts, CHNO·CHClO (I) and CHNO·CHBrO (II), and the 4-iodo-benzoate salt CHNO·CHIO (III), the ions are linked by N-H⋯O hydrogen bonds, forming centrosymmetric (12) four-ion aggregates; a similar aggregate is formed in the 2-chloro-benzoate salt (V), isomeric with (I). In the 2-fluoro-benzoate salt CHNO·CHFO (IV), and the isomorphous pair of salts, the 2-bromo-benzoate (VI), isomeric with (II) and 2-iodo-benzoate (VII), isomeric with (III), N-H⋯O and C-H⋯π(arene) interactions link the components into three-dimensional arrays.

A very short O-H⋯O hydrogen bond in the structure of clozapinium hydrogen bis-(3,5-di-nitro-benzoate).

In the title salt {systematic name: 4-[6-chloro-2,9-di-aza-tri-cyclo-[9.4.0.

Order disorder in two isomorphous pyrazolone-substituted diethyl propane-dioates prepared using a three-component one-pot reaction under solvent-free conditions.

Two new substituted propane-dioate esters have been synthesized using a three-component solvent-free thermal reaction between diethyl propane-dioate (diethyl malonate), 5-chloro-3-methyl-1-phenyl-1-pyrazole-4-carbaldehyde and an aryl azide, forming two new C-C bonds in a single step. The products diethyl ()-2-[(4-bromo-phen-yl)(5-methyl-3-oxo-2-phenyl-2,3-di-hydro-1-pyrazol-4-yl)meth-yl]propane-dioate, CHBrNO (I), and diethyl ()-2-[(4-chloro-phen-yl)(5-methyl-3-oxo-2-phenyl-2,3-di-hydro-1-pyrazol-4-yl)meth-yl]propane-dioate, CHClNO (II), are isomorphous, with ' = 2 in space group 2/. The two independent mol-ecules in compound (I) are both fully ordered, while each of the independent mol-ecules in compound (II) is disordered, but in different ways.

Bis[tris-(pyridin-2-yl)amine]-iron(II) tris-(di-cyano-methyl-idene)methane-diide.

In the title compound, [Fe{(CHN)N}][C{C(CN)}], both ions lie across centres of inversion, with the anion being statistically disordered over two sets of atomic sites having equal occupancy. The cation and anion have approximate and 32 symmetry, respectively, and the Fe-N bond lengths indicate low-spin Fe. A combination of two-centre C-H⋯N and three-centre C-H⋯(N) hydrogen bonds link the ions into complex sheets.

4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and regiochemistry.

Structures are reported for two matched sets of substituted 4-styrylquinolines which were prepared by the formation of the heterocyclic ring in cyclocondensation reactions between 1-(2-aminophenyl)-3-arylprop-2-en-1-ones with 1,3-dicarbonyl compounds. (E)-3-Acetyl-4-[2-(4-methoxyphenyl)ethenyl]-2-methylquinoline, CHNO, (I), (E)-3-acetyl-4-[2-(4-bromophenyl)ethenyl]-2-methylquinoline, CHBrNO, (II), and (E)-3-acetyl-2-methyl-4-{2-[4-(trifluoromethyl)phenyl]ethenyl}quinoline, CHFNO, (III), are isomorphous and in each structure the molecules are linked by a single C-H..

The crystal structures of salts of -(4-fluoro-phen-yl)piperazine with four aromatic carb-oxy-lic acids and with picric acid.

The structures are reported for five salts formed by reactions between -(4-fluoro-phen-yl)piperazine and aromatic acids. In 4-(4-fluoro-phen-yl)piperazin-1-ium 2-fluoro-benzoate monohydrate, CHFN ·CHFO ·HO, (I), the components are linked by a combination of N-H⋯O and O-H⋯O hydrogen bonds to form a chain of alternating (12) and (16) rings. The ionic components of 4-(4-fluoro-phen-yl)piperazin-1-ium 2-bromo-benzoate 0.