Acta Crystallographica Section C
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Acta Crystallographica Section C: Structural Chemistry is the journal of choice for publishing any science to which structure contributes a role, with a particular focus on the field of structural chemistry. As well as research papers, the journal publishes lead articles, feature articles, letters to the editor and scientific comments. The journal specializes in the rapid publication of articles that highlight interesting research enabled by the determination, calculation or analysis of small-molecule crystal and molecular structures in the chemical sciences. The journal has a reputation for publishing high-quality crystal structures, but articles describing difficult or challenging structures and the strategies used to handle them are also welcomed.enCopyright (c) 2024 International Union of Crystallography2024-03-28International Union of CrystallographyInternational Union of Crystallographyhttp://journals.iucr.orgurn:issn:2053-2296Acta Crystallographica Section C: Structural Chemistry is the journal of choice for publishing any science to which structure contributes a role, with a particular focus on the field of structural chemistry. As well as research papers, the journal publishes lead articles, feature articles, letters to the editor and scientific comments. The journal specializes in the rapid publication of articles that highlight interesting research enabled by the determination, calculation or analysis of small-molecule crystal and molecular structures in the chemical sciences. The journal has a reputation for publishing high-quality crystal structures, but articles describing difficult or challenging structures and the strategies used to handle them are also welcomed.text/htmlActa Crystallographica Section C: Structural Chemistry, Volume 80, Part 4, 2024textweekly12002-01-15T00:00+00:004802024-03-28Copyright (c) 2024 International Union of CrystallographyActa Crystallographica Section C: Structural Chemistry91urn:issn:2053-2296med@iucr.orgMarch 20242024-03-28Acta Crystallographica Section Chttp://journals.iucr.org/logos/rss10c.gif
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Still imageCrystal structure and analytical profile of 1,2-diphenyl-2-pyrrolidin-1-ylethanone hydrochloride or `α-D2PV': a synthetic cathinone seized by law enforcement, along with its diluent sugar, myo-inositol
http://scripts.iucr.org/cgi-bin/paper?eq3015
A confiscated package of street drugs was characterized by the usual mass spectral (MS) and FT–IR analyses. The confiscated powder material was highly crystalline and was found to consist of two very different species, accidentally of sizes convenient for X-ray diffraction. Thus, one each was selected and redundant complete sets of data were collected at 100 K using Cu Kα radiation. The selected crystals contained: (a) 1,2-diphenyl-2-(pyrrolidin-1-yl)ethanone hydrochloride hemihydrate or 1-(2-oxo-1,2-diphenylethyl)pyrrolidin-1-ium chloride hemihydrate, C18H20NO+·Cl−·0.5H2O, (I), a synthetic cathinone called `α-D2PV', and (b) the sugar myo-inositol, C6H12O6, (II), probably the only instance in which the drug and its diluent have been fully characterized from a single confiscated sample. Moreover, the structural details of both are rather attractive showing: (i) interesting hydrogen bonding observed in pairwise interactions by the drug molecules, mediated by the chloride counter-anions and the waters of crystallization, and (ii) π–π interactions in the case of the phenyl rings of the drug which are of two different types, namely, π–π stacking and edge-to-π. Finally, the inositol crystallizes with Z′ = 2 and the resulting diastereoisomers were examined by overlay techniques.Copyright (c) 2024 International Union of Crystallographyurn:issn:2053-2296Wood, M.R.Bernal, I.Lalancette, R.A.2024-01-22doi:10.1107/S2053229624000561International Union of CrystallographyA confiscated package of street drugs was highly crystalline and was found to consist of two very different species accidentally of sizes convenient for X-ray diffraction, namely, 1,2-diphenyl-2-(pyrrolidin-1-yl)ethanone hydrochloride or `α-D2PV' and the sugar myo-inositol.ENcrystal structurecathinonesbath saltsracemic drugssugarsinositolasymmetric unitsmolecular overlaysnovel psychoactive substancesπ–π interactionshydrogen bondingA confiscated package of street drugs was characterized by the usual mass spectral (MS) and FT–IR analyses. The confiscated powder material was highly crystalline and was found to consist of two very different species, accidentally of sizes convenient for X-ray diffraction. Thus, one each was selected and redundant complete sets of data were collected at 100 K using Cu Kα radiation. The selected crystals contained: (a) 1,2-diphenyl-2-(pyrrolidin-1-yl)ethanone hydrochloride hemihydrate or 1-(2-oxo-1,2-diphenylethyl)pyrrolidin-1-ium chloride hemihydrate, C18H20NO+·Cl−·0.5H2O, (I), a synthetic cathinone called `α-D2PV', and (b) the sugar myo-inositol, C6H12O6, (II), probably the only instance in which the drug and its diluent have been fully characterized from a single confiscated sample. Moreover, the structural details of both are rather attractive showing: (i) interesting hydrogen bonding observed in pairwise interactions by the drug molecules, mediated by the chloride counter-anions and the waters of crystallization, and (ii) π–π interactions in the case of the phenyl rings of the drug which are of two different types, namely, π–π stacking and edge-to-π. Finally, the inositol crystallizes with Z′ = 2 and the resulting diastereoisomers were examined by overlay techniques.text/htmlCrystal structure and analytical profile of 1,2-diphenyl-2-pyrrolidin-1-ylethanone hydrochloride or `α-D2PV': a synthetic cathinone seized by law enforcement, along with its diluent sugar, myo-inositoltext4802024-01-22Copyright (c) 2024 International Union of CrystallographyActa Crystallographica Section Cresearch papers919721938652193866A twofold interpenetrated two-dimensional zinc(II) coordination polymer for the highly sensitive detection of nitrofurantoin in aqueous medium
http://scripts.iucr.org/cgi-bin/paper?dg3050
A novel ZnII coordination polymer, namely, poly[{μ2-bis[4-(2-methyl-1H-imidazol-1-yl)phenyl]methanone-κ2N3:N3′}(μ2-5-bromobenzene-1,3-dicarboxylato-κ2O1:O3)zinc(II)], [Zn(C8H3BrO4)(C21H18N4O)]n or [Zn(Br-BDC)(MIPMO)]n, (I), has been synthesized by the solvothermal method using 5-bromoisophthalic acid (Br-H2BDC), bis[4-(2-methyl-1H-imidazol-1-yl)phenyl]methanone (MIPMO) and Zn(NO3)2·6H2O. Structure analysis showed that compound (I) displays twofold parallel interwoven sql nets. Fluorescence experiments confirmed that the compound can sensitively and selectively detect nitrofurantoin (NFT) in aqueous medium. In addition, the possible fluorescence quenching mechanisms of compound (I) toward NFT are investigated.Copyright (c) 2024 International Union of Crystallographyurn:issn:2053-2296Wang, Y.Cheng, W.W.Mou, Y.Wen, S.Wang, D.Xue, Y.S.2024-03-12doi:10.1107/S2053229624002171International Union of CrystallographyA zinc(II) compound, prepared by reaction of Zn(NO3)2·6H2O with 5-bromoisophthalic acid and bis[4-(2-methyl-1H-imidazol-1-yl)phenyl]methanone in a mixture of water and dimethylacetamide, possesses a new two-dimensional twofold interpenetrated network, which can be simplified as a sql net. The compound displays a highly selective and sensitive detection for nitrofurantoin (NFT) in aqueous solution. In addition, the possible fluorescence quenching mechanisms toward NFT are investigated.ENcoordination polymermethanonecrystal structure5-bromoisophthalic acidfluorescence recognitionantibioticnitrofurantoin detectionA novel ZnII coordination polymer, namely, poly[{μ2-bis[4-(2-methyl-1H-imidazol-1-yl)phenyl]methanone-κ2N3:N3′}(μ2-5-bromobenzene-1,3-dicarboxylato-κ2O1:O3)zinc(II)], [Zn(C8H3BrO4)(C21H18N4O)]n or [Zn(Br-BDC)(MIPMO)]n, (I), has been synthesized by the solvothermal method using 5-bromoisophthalic acid (Br-H2BDC), bis[4-(2-methyl-1H-imidazol-1-yl)phenyl]methanone (MIPMO) and Zn(NO3)2·6H2O. Structure analysis showed that compound (I) displays twofold parallel interwoven sql nets. Fluorescence experiments confirmed that the compound can sensitively and selectively detect nitrofurantoin (NFT) in aqueous medium. In addition, the possible fluorescence quenching mechanisms of compound (I) toward NFT are investigated.text/htmlA twofold interpenetrated two-dimensional zinc(II) coordination polymer for the highly sensitive detection of nitrofurantoin in aqueous mediumtext4802024-03-12Copyright (c) 2024 International Union of CrystallographyActa Crystallographica Section Cresearch papers981032338137Syntheses, crystal structures and intermolecular interactions of six novel pyrimidin-2-yl-substituted triaryltriazoles
http://scripts.iucr.org/cgi-bin/paper?vp3032
Six new pyrimidin-2-yl-substituted triaryltriazoles, namely, 4-(4-R-phenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazoles [L1: R = methoxy (OCH3); L2: R = methyl (CH3); L3: R = nil (H); L4: R = bromo (Br); L5: R = chloro (Cl); L6: R = fluoro (F)] have been successfully synthesized with yields in the range 68.3–81.7%. Compounds L1–6 have been characterized by UV–Vis, FT–IR, 1H NMR and ESI–MS spectroscopy, and elemental analysis. In addition, the structures of L2–6 and the ethanol monosolvate of L2 (L2·C2H5OH) have been determined by single-crystal X-ray diffraction. A combination of intermolecular O—H...N, C—H...O, C—H...N and C—H...π hydrogen bonds connects the components of L2·C2H5OH into a three-dimensional (3D) framework. A combination of three intermolecular C—H...N hydrogen bonds links the molecules of L2 or L3 into two different 3D networks. Both L4 and L5 show a similar 3D net structure through two intermolecular C—H...N hydrogen bonds and one kind of C—H...π interaction. However, L6 displays a more complicated 3D net structure via three intermolecular C—H...N hydrogen bonds and one kind of C—H...π interaction. Notably, an interaction between the π-electrons and the lone-pair p-electrons of a halogen atom (Br, Cl and F) is observed in L4–6, which will further stabilize the 3D networks. The intermolecular interactions in L2·C2H5OH and L2–6 were further investigated by 3D Hirshfeld surface analyses and 2D fingerprint plots to show that the prominent interactions are H...H, N...H/H...N and C...H/H...C contacts.Copyright (c) 2024 International Union of Crystallographyurn:issn:2053-2296Song, H.Peng, R.Zuo, Y.Wang, T.Zhu, D.2024-03-12doi:10.1107/S2053229624002018International Union of CrystallographySix novel pyrimidin-2-yl-based triaryltriazoles, namely, 4-(4-R-phenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazoles (with R = OCH3, CH3, H, Br, Cl and F) were synthesized and characterized by X-ray crystallography.ENsynthesiscrystal structurepyrimidinetriaryltriazolespectral characterizationhydrogen bondingHirshfeld surface analysisSix new pyrimidin-2-yl-substituted triaryltriazoles, namely, 4-(4-R-phenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazoles [L1: R = methoxy (OCH3); L2: R = methyl (CH3); L3: R = nil (H); L4: R = bromo (Br); L5: R = chloro (Cl); L6: R = fluoro (F)] have been successfully synthesized with yields in the range 68.3–81.7%. Compounds L1–6 have been characterized by UV–Vis, FT–IR, 1H NMR and ESI–MS spectroscopy, and elemental analysis. In addition, the structures of L2–6 and the ethanol monosolvate of L2 (L2·C2H5OH) have been determined by single-crystal X-ray diffraction. A combination of intermolecular O—H...N, C—H...O, C—H...N and C—H...π hydrogen bonds connects the components of L2·C2H5OH into a three-dimensional (3D) framework. A combination of three intermolecular C—H...N hydrogen bonds links the molecules of L2 or L3 into two different 3D networks. Both L4 and L5 show a similar 3D net structure through two intermolecular C—H...N hydrogen bonds and one kind of C—H...π interaction. However, L6 displays a more complicated 3D net structure via three intermolecular C—H...N hydrogen bonds and one kind of C—H...π interaction. Notably, an interaction between the π-electrons and the lone-pair p-electrons of a halogen atom (Br, Cl and F) is observed in L4–6, which will further stabilize the 3D networks. The intermolecular interactions in L2·C2H5OH and L2–6 were further investigated by 3D Hirshfeld surface analyses and 2D fingerprint plots to show that the prominent interactions are H...H, N...H/H...N and C...H/H...C contacts.text/htmlSyntheses, crystal structures and intermolecular interactions of six novel pyrimidin-2-yl-substituted triaryltriazolestext4802024-03-12Copyright (c) 2024 International Union of CrystallographyActa Crystallographica Section Cresearch papers104114233643023364312336432233643323364342336435Crystal structure, intermolecular interactions, charge–density distribution and ADME properties of the acridinium 4-nitrobenzoate and 2-amino-3-methylpyridinium 4-nitrobenzoate salts: a combined experimental and theoretical study
http://scripts.iucr.org/cgi-bin/paper?ef3054
Acridines are a class of bioactive agents which exhibit high biological stability and the ability to intercalate with DNA; they have a wide range of applications. Pyridine derivatives have a wide range of biological activities. To enhance the properties of acridine and 2-amino-3-methylpyridine as the active pharmaceutical ingredient (API), 4-nitrobenzoic acid was chosen as a coformer. In the present study, a mixture of acridine and 4-nitrobenzoic acid forms the salt acridinium 4-nitrobenzoate, C13H10N+·C7H4NO4− (I), whereas a mixture of 2-amino-3-methylpyridine and 4-nitrobenzoic acid forms the salt 2-amino-3-methylpyridinium 4-nitrobenzoate, C6H9N2+·C7H4NO4− (II). In both salts, protonation takes place at the ring N atom. The crystal structure of both salts is predominantly governed by hydrogen-bond interactions. In salt I, C—H...O and N—H...O interactions form an infinite chain in the crystal, whereas in salt II, intermolecular N—H...O interactions form an eight-membered R22(8) ring motif. A theoretical charge–density analysis reveals the charge–density distribution of the inter- and intramolecular interactions of both salts. An in-silico ADME analysis predicts the druglikeness properties of both salts and the results confirm that both salts are potential drug candidates with good bioavailability scores and there is no violation of the Lipinski rules, which supports the druglikeness properties of both salts. However, although both salts exhibit drug-like properties, salt I has higher gastrointestinal absorption than salt II and hence it may be considered a potential drug candidate.Copyright (c) 2024 International Union of Crystallographyurn:issn:2053-2296Balasubramanian, H.Mariappan, P.R.Poomani, K.2024-03-19doi:10.1107/S2053229624002250International Union of CrystallographyTo enhance the properties of acridine and 2-amino-3-methylpyridine, 4-nitrobenzoic acid was chosen as a coformer, resulting in the formation of salts. Although both salts exhibit drug-like properties, the former salt has higher gastrointestinal absorption than the latter and hence it may be considered a potential drug candidate.ENintermolecular interactioncharge-density distributioncrystal structureADME propertiesacridiniumnitrobenzoatesalttheoretical studyAcridines are a class of bioactive agents which exhibit high biological stability and the ability to intercalate with DNA; they have a wide range of applications. Pyridine derivatives have a wide range of biological activities. To enhance the properties of acridine and 2-amino-3-methylpyridine as the active pharmaceutical ingredient (API), 4-nitrobenzoic acid was chosen as a coformer. In the present study, a mixture of acridine and 4-nitrobenzoic acid forms the salt acridinium 4-nitrobenzoate, C13H10N+·C7H4NO4− (I), whereas a mixture of 2-amino-3-methylpyridine and 4-nitrobenzoic acid forms the salt 2-amino-3-methylpyridinium 4-nitrobenzoate, C6H9N2+·C7H4NO4− (II). In both salts, protonation takes place at the ring N atom. The crystal structure of both salts is predominantly governed by hydrogen-bond interactions. In salt I, C—H...O and N—H...O interactions form an infinite chain in the crystal, whereas in salt II, intermolecular N—H...O interactions form an eight-membered R22(8) ring motif. A theoretical charge–density analysis reveals the charge–density distribution of the inter- and intramolecular interactions of both salts. An in-silico ADME analysis predicts the druglikeness properties of both salts and the results confirm that both salts are potential drug candidates with good bioavailability scores and there is no violation of the Lipinski rules, which supports the druglikeness properties of both salts. However, although both salts exhibit drug-like properties, salt I has higher gastrointestinal absorption than salt II and hence it may be considered a potential drug candidate.text/htmlCrystal structure, intermolecular interactions, charge–density distribution and ADME properties of the acridinium 4-nitrobenzoate and 2-amino-3-methylpyridinium 4-nitrobenzoate salts: a combined experimental and theoretical studytext4802024-03-19Copyright (c) 2024 International Union of CrystallographyActa Crystallographica Section Cresearch papers11512222406412298314Three polymorphs of a new N,N′-dipropylated isoindigo derivative
http://scripts.iucr.org/cgi-bin/paper?vp3033
A newly synthesized N,N′-dipropyl-substituted isoindigo derivative, namely, 1-propyl-3-(1-propyl-1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-2H-indol-2-one, C22H22N2O2, was found to have three polymorphic forms (denoted Forms I, II and III) under various crystallization conditions. Crystal structure analysis indicated that Form III had a significantly different molecular conformation from the other two polymorphs. Their different packing arrangements were correlated with differences in the intermolecular interactions. Thermal measurements revealed that Forms I and II are enantiotropically related, and Form II exhibits thermally dynamic behaviour.Copyright (c) 2024 International Union of Crystallographyurn:issn:2053-2296Jozuka, W.Kim, S.Matsumoto, S.2024-03-21doi:10.1107/S2053229624002481International Union of CrystallographyA dipropyl-substituted isoindigo derivative has three polymorphs with different molecular conformations and arrangements.ENcrystal structureisoindigoindolonedyestuffpolymorphsthermal measurementsA newly synthesized N,N′-dipropyl-substituted isoindigo derivative, namely, 1-propyl-3-(1-propyl-1,2-dihydro-2-oxo-3H-indol-3-ylidene)-1,3-dihydro-2H-indol-2-one, C22H22N2O2, was found to have three polymorphic forms (denoted Forms I, II and III) under various crystallization conditions. Crystal structure analysis indicated that Form III had a significantly different molecular conformation from the other two polymorphs. Their different packing arrangements were correlated with differences in the intermolecular interactions. Thermal measurements revealed that Forms I and II are enantiotropically related, and Form II exhibits thermally dynamic behaviour.text/htmlThree polymorphs of a new N,N′-dipropylated isoindigo derivativetext4802024-03-21Copyright (c) 2024 International Union of CrystallographyActa Crystallographica Section Cresearch papers123128232182523218262321827Synthesis, crystal structure and in-silico evaluation of arylsulfonamide Schiff bases for potential activity against colon cancer
http://scripts.iucr.org/cgi-bin/paper?ef3052
This report presents a comprehensive investigation into the synthesis and characterization of Schiff base compounds derived from benzenesulfonamide. The synthesis process, involved the reaction between N-cycloamino-2-sulfanilamide and various substituted o-salicylaldehydes, resulted in a set of compounds that were subjected to rigorous characterization using advanced spectral techniques, including 1H NMR, 13C NMR and FT–IR spectroscopy, and single-crystal X-ray diffraction. Furthermore, an in-depth assessment of the synthesized compounds was conducted through Absorption, Distribution, Metabolism, Excretion and Toxicity (ADMET) analysis, in conjunction with docking studies, to elucidate their pharmacokinetic profiles and potential. Impressively, the ADMET analysis showcased encouraging drug-likeness properties of the newly synthesized Schiff bases. These computational findings were substantiated by molecular properties derived from density functional theory (DFT) calculations using the B3LYP/6-31G* method within the Jaguar Module of Schrödinger 2023-2 from Maestro (Schrodinger LLC, New York, USA). The exploration of frontier molecular orbitals (HOMO and LUMO) enabled the computation of global reactivity descriptors (GRDs), encompassing charge separation (Egap) and global softness (S). Notably, within this analysis, one Schiff base, namely, 4-bromo-2-{N-[2-(pyrrolidine-1-sulfonyl)phenyl]carboximidoyl}phenol, 20, emerged with the smallest charge separation (ΔEgap = 3.5780 eV), signifying heightened potential for biological properties. Conversely, 4-bromo-2-{N-[2-(piperidine-1-sulfonyl)phenyl]carboximidoyl}phenol, 17, exhibited the largest charge separation (ΔEgap = 4.9242 eV), implying a relatively lower propensity for biological activity. Moreover, the synthesized Schiff bases displayed remarkeable inhibition of tankyrase poly(ADP-ribose) polymerase enzymes, integral in colon cancer, surpassing the efficacy of a standard drug used for the same purpose. Additionally, their bioavailability scores aligned closely with established medications such as trifluridine and 5-fluorouracil. The exploration of molecular electrostatic potential through colour mapping delved into the electronic behaviour and reactivity tendencies intrinsic to this diverse range of molecules.Copyright (c) 2024 International Union of Crystallographyurn:issn:2053-2296Kolade, S.O.Aina, O.S.Gordon, A.T.Hosten, E.C.Olasupo, I.A.Ogunlaja, A.S.Asekun, O.T.Familoni, O.B.2024-03-28doi:10.1107/S205322962400233XInternational Union of CrystallographyThe successful synthesis, characterization and analysis of intermolecular interactions of arylsulfonamide Schiff bases have been achieved, alongside their evaluation for inhibitory effects on tankyrase poly(ADP-ribose) polymerase in the context of colon cancer, through in-silico testing.ENSchiff basearylsulfonamidecolon cancercrystal structuremolecular dockingADMETThis report presents a comprehensive investigation into the synthesis and characterization of Schiff base compounds derived from benzenesulfonamide. The synthesis process, involved the reaction between N-cycloamino-2-sulfanilamide and various substituted o-salicylaldehydes, resulted in a set of compounds that were subjected to rigorous characterization using advanced spectral techniques, including 1H NMR, 13C NMR and FT–IR spectroscopy, and single-crystal X-ray diffraction. Furthermore, an in-depth assessment of the synthesized compounds was conducted through Absorption, Distribution, Metabolism, Excretion and Toxicity (ADMET) analysis, in conjunction with docking studies, to elucidate their pharmacokinetic profiles and potential. Impressively, the ADMET analysis showcased encouraging drug-likeness properties of the newly synthesized Schiff bases. These computational findings were substantiated by molecular properties derived from density functional theory (DFT) calculations using the B3LYP/6-31G* method within the Jaguar Module of Schrödinger 2023-2 from Maestro (Schrodinger LLC, New York, USA). The exploration of frontier molecular orbitals (HOMO and LUMO) enabled the computation of global reactivity descriptors (GRDs), encompassing charge separation (Egap) and global softness (S). Notably, within this analysis, one Schiff base, namely, 4-bromo-2-{N-[2-(pyrrolidine-1-sulfonyl)phenyl]carboximidoyl}phenol, 20, emerged with the smallest charge separation (ΔEgap = 3.5780 eV), signifying heightened potential for biological properties. Conversely, 4-bromo-2-{N-[2-(piperidine-1-sulfonyl)phenyl]carboximidoyl}phenol, 17, exhibited the largest charge separation (ΔEgap = 4.9242 eV), implying a relatively lower propensity for biological activity. Moreover, the synthesized Schiff bases displayed remarkeable inhibition of tankyrase poly(ADP-ribose) polymerase enzymes, integral in colon cancer, surpassing the efficacy of a standard drug used for the same purpose. Additionally, their bioavailability scores aligned closely with established medications such as trifluridine and 5-fluorouracil. The exploration of molecular electrostatic potential through colour mapping delved into the electronic behaviour and reactivity tendencies intrinsic to this diverse range of molecules.text/htmlSynthesis, crystal structure and in-silico evaluation of arylsulfonamide Schiff bases for potential activity against colon cancertext4802024-03-28Copyright (c) 2024 International Union of CrystallographyActa Crystallographica Section Cresearch papers1291422305610