Acta Crystallographica Section E: Crystallographic Communications最新文献_第3页

Crystal structures of three salts of the triphenylsulfonium ion

IF 0.5 Q4 CRYSTALLOGRAPHY

Acta Crystallographica Section E: Crystallographic Communications

Pub Date : 2025-02-01 DOI: 10.1107/S2056989025000118

Rylan Artis , Waylan Callaway , Elizabeth Heyward , Naomi Reyes , Gavin Roberts , Kaitlyn Van Ostenbridge , Clifford W. Padgett , Will E. Lynch

The crystal structures of three salts of triphenylsulfonium ion are reported, namely, triphenylsulfonium triiodide (I), triphenylsulfonium perchorate (II), triphenylsulfonium hexafluorophosphate (III).

The reactions of triphenylsulfonium chloride ([TPS][Cl]) with various acids in methanol yield the corresponding salts triphenylsulfonium triiodide, C₁₈H₁₅S⁺·I₃⁻ or [TPS][I₃] (I), triphenylsulfonium perchlorate, C₁₈H₁₅S⁺·ClO₄⁻ or [TPS][ClO₄] (II), and triphenylsulfonium hexafluorophosphate, C₁₈H₁₅S⁺·PF₆⁻ or [TPS][PF₆] (III), as crystalline products. These crystals were structurally characterized by single-crystal X-ray diffraction. In all three compounds, the sulfur atom in the triphenylsulfonium cation adopts a distorted trigonal–pyramidal geometry. [TPS][I₃] (I) and [TPS][PF₆] (III) both crystallize in the space group P2₁/n, while [TPS][ClO₄] (II) crystallizes in P2₁. The S—C bond lengths are comparable across the three salts, and the S—C—S bond angles are consistently between 102 and 106°. Hirshfeld surface analyses reveal that each structure is dominated by hydrogen-based intermolecular contacts, supplemented by anion-specific interactions such as I⋯H in (I), O⋯H in (II), and F⋯H in (III). These contacts organize the ions into mono-periodic ribbon- or chain-like arrangements. No significant π–π stacking is observed.

{"title":"Crystal structures of three salts of the triphenylsulfonium ion","authors":"Rylan Artis , Waylan Callaway , Elizabeth Heyward , Naomi Reyes , Gavin Roberts , Kaitlyn Van Ostenbridge , Clifford W. Padgett , Will E. Lynch","doi":"10.1107/S2056989025000118","DOIUrl":"10.1107/S2056989025000118","url":null,"abstract":"<div><div>The crystal structures of three salts of triphenylsulfonium ion are reported, namely, triphenylsulfonium triiodide (I), triphenylsulfonium perchorate (II), triphenylsulfonium hexafluorophosphate (III).</div></div><div><div>The reactions of triphenylsulfonium chloride ([TPS][Cl]) with various acids in methanol yield the corresponding salts triphenylsulfonium triiodide, C18H15S+·I3− or [TPS][I3] (I), triphenylsulfonium perchlorate, C18H15S+·ClO4− or [TPS][ClO4] (II), and triphenylsulfonium hexafluorophosphate, C18H15S+·PF6− or [TPS][PF6] (III), as crystalline products. These crystals were structurally characterized by single-crystal X-ray diffraction. In all three compounds, the sulfur atom in the triphenylsulfonium cation adopts a distorted trigonal–pyramidal geometry. [TPS][I3] (I) and [TPS][PF6] (III) both crystallize in the space group P21/n, while [TPS][ClO4] (II) crystallizes in P21. The S—C bond lengths are comparable across the three salts, and the S—C—S bond angles are consistently between 102 and 106°. Hirshfeld surface analyses reveal that each structure is dominated by hydrogen-based intermolecular contacts, supplemented by anion-specific interactions such as I⋯H in (I), O⋯H in (II), and F⋯H in (III). These contacts organize the ions into mono-periodic ribbon- or chain-like arrangements. No significant π–π stacking is observed.</div></div>","PeriodicalId":7367,"journal":{"name":"Acta Crystallographica Section E: Crystallographic Communications","volume":"81 2","pages":"Pages 114-119"},"PeriodicalIF":0.5,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11799790/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143381482","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Crystal structures of zinc(II) coordination complexes with isoquinoline N-oxide

IF 0.5 Q4 CRYSTALLOGRAPHY

Acta Crystallographica Section E: Crystallographic Communications

Pub Date : 2025-02-01 DOI: 10.1107/S2056989025000180

Erin N. Groneck , Nathan Peek , Will E. Lynch , Clifford W. Padgett

<div><div>The structures of five related zinc coordination compounds with isoquinoline N-oxide and other ligands or counter-ions are presented.</div></div><div><div>The reaction of one equivalent of zinc(II) halide salts with two equivalents of isoquinoline N-oxide (iQNO; C9H7NO) in methanol yields compounds of the general formula [ZnX2(iQNO)2], with X = Cl− (I), Br− (II) and I− (III). However, starting with zinc(II) perchlorate or nitrate leads to the formation of complex ions with the compositions [Zn(iQNO)6](X)2 for X = ClO4− (IV), and [Zn(iQNO)(H2O)5](iQNO)2X2 for X = NO3− (V). Complexes (I), (II) and (III), namely dichloridobis(isoquinoline N-oxide-κO)zinc(II) [ZnCl2(C9H7NO)2], dibromidobis(isoquinoline N-oxide-κO)zinc(II) [ZnBr2(C9H7NO)2], and diiodidobis(isoquinoline N-oxide-κO)zinc(II) [ZnI2(C9H7NO)2], each exhibit a distorted tetrahedral coordination geometry around the zinc(II) ion coordinated by two iQNO ligands bound through the oxygen atom and two halide ions. The zinc ion lies on a crystallographic twofold axis in the bromo complex. The X—Zn—X bond angles are approximately 15–17° larger than the O—Zn—O bond angles resulting in the observed tetrahedral distortion. In complex (IV), hexakis(isoquinoline N-oxide-κO)zinc(II) bis(perchlorate), [Zn(C9H7NO)6](ClO4)2, the zinc(II) ion occupies a special position with 3 site symmetry and is octahedrally coordinated by six iQNO ligands, albeit with slight distortions evidenced by a spread of cis bond angles from 85.82 (4) to 94.18 (4)°. The chlorine atom of the perchlorate anion lies on a crystallographic threefold axis. Finally, complex (V) crystallizes with a pseudo-octahedral geometry; pentaaqua(isoquinoline N-oxide-κO)zinc(II) dinitrate–isoquinoline N-oxide (1/2), [Zn(C9H7NO)(H2O)5](NO3)2·2(C9H7NO). The nitrate ions and non-coordinated iQNO molecules engage in π-stacking and hydrogen-bonding interactions with the coordinated water molecules. The iQNO—Zn—O equatorial bond angles range from 88.98 (9) to 94.90 (9)°, with the largest deviation from a perfect octahedral angle attributed to the influence of a weak C—H⋯O (from water) interaction (2.28

{"title":"Crystal structures of zinc(II) coordination complexes with isoquinoline N-oxide","authors":"Erin N. Groneck , Nathan Peek , Will E. Lynch , Clifford W. Padgett","doi":"10.1107/S2056989025000180","DOIUrl":"10.1107/S2056989025000180","url":null,"abstract":"<div><div>The structures of five related zinc coordination compounds with isoquinoline N-oxide and other ligands or counter-ions are presented.</div></div><div><div>The reaction of one equivalent of zinc(II) halide salts with two equivalents of isoquinoline N-oxide (iQNO; C9H7NO) in methanol yields compounds of the general formula [ZnX2(iQNO)2], with X = Cl− (I), Br− (II) and I− (III). However, starting with zinc(II) perchlorate or nitrate leads to the formation of complex ions with the compositions [Zn(iQNO)6](X)2 for X = ClO4− (IV), and [Zn(iQNO)(H2O)5](iQNO)2X2 for X = NO3− (V). Complexes (I), (II) and (III), namely dichloridobis(isoquinoline N-oxide-κO)zinc(II) [ZnCl2(C9H7NO)2], dibromidobis(isoquinoline N-oxide-κO)zinc(II) [ZnBr2(C9H7NO)2], and diiodidobis(isoquinoline N-oxide-κO)zinc(II) [ZnI2(C9H7NO)2], each exhibit a distorted tetrahedral coordination geometry around the zinc(II) ion coordinated by two iQNO ligands bound through the oxygen atom and two halide ions. The zinc ion lies on a crystallographic twofold axis in the bromo complex. The X—Zn—X bond angles are approximately 15–17° larger than the O—Zn—O bond angles resulting in the observed tetrahedral distortion. In complex (IV), hexakis(isoquinoline N-oxide-κO)zinc(II) bis(perchlorate), [Zn(C9H7NO)6](ClO4)2, the zinc(II) ion occupies a special position with 3 site symmetry and is octahedrally coordinated by six iQNO ligands, albeit with slight distortions evidenced by a spread of cis bond angles from 85.82 (4) to 94.18 (4)°. The chlorine atom of the perchlorate anion lies on a crystallographic threefold axis. Finally, complex (V) crystallizes with a pseudo-octahedral geometry; pentaaqua(isoquinoline N-oxide-κO)zinc(II) dinitrate–isoquinoline N-oxide (1/2), [Zn(C9H7NO)(H2O)5](NO3)2·2(C9H7NO). The nitrate ions and non-coordinated iQNO molecules engage in π-stacking and hydrogen-bonding interactions with the coordinated water molecules. The iQNO—Zn—O equatorial bond angles range from 88.98 (9) to 94.90 (9)°, with the largest deviation from a perfect octahedral angle attributed to the influence of a weak C—H⋯O (from water) interaction (2.28","PeriodicalId":7367,"journal":{"name":"Acta Crystallographica Section E: Crystallographic Communications","volume":"81 2","pages":"Pages 132-139"},"PeriodicalIF":0.5,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11799800/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143381487","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis, crystal structure and Hirshfeld surface analysis of 5,5-diphenyl-2-[2-(propan-2-ylidene)hydrazin-1-yl]-4,5-dihydro-1H-imidazol-4-one N,N-dimethylformamide hemisolvate

IF 0.5 Q4 CRYSTALLOGRAPHY

Acta Crystallographica Section E: Crystallographic Communications

Pub Date : 2025-02-01 DOI: 10.1107/S2056989025000076

Abderrazzak El Moutaouakil Ala Allah , Benson M. Kariuki , Walid Guerrab , Abdulsalam Alsubari , Musa A. Said , Joel T. Mague , Youssef Ramli

The asymmetric unit consists of two independent molecules of the substituted imidazolone having different conformations, and one molecule of solvent DMF. The two imidazolone molecules are linked by N—H⋯N and C—H⋯O hydrogen bonds and the DMF is joined to one of these by a N—H⋯O hydrogen bond. Additional N—H⋯N and C—H⋯O hydrogen bonds link these groups into corrugated layers parallel to the (101) plane with the layers joined by C—H⋯π (ring) interactions.

The asymmetric unit of the title structure, 2C₁₈H₁₈N₄O₂·C₃H₇NO, consists of two independent molecules of the substituted imidazolone having different conformations, and one molecule of solvent DMF. The two imidazolone molecules are linked by N—H⋯N and C—H⋯O hydrogen bonds and the DMF is joined to one of these by an N—H⋯O hydrogen bond. Additional N—H⋯N and C—H⋯O hydrogen bonds link these groups into corrugated layers parallel to the (101) plane with the layers joined by C—H⋯π (ring) interactions. A Hirshfeld surface analysis indicated that H⋯H interactions account for over half of the intermolecular contacts.

{"title":"Synthesis, crystal structure and Hirshfeld surface analysis of 5,5-diphenyl-2-[2-(propan-2-ylidene)hydrazin-1-yl]-4,5-dihydro-1H-imidazol-4-one N,N-dimethylformamide hemisolvate","authors":"Abderrazzak El Moutaouakil Ala Allah , Benson M. Kariuki , Walid Guerrab , Abdulsalam Alsubari , Musa A. Said , Joel T. Mague , Youssef Ramli","doi":"10.1107/S2056989025000076","DOIUrl":"10.1107/S2056989025000076","url":null,"abstract":"<div><div>The asymmetric unit consists of two independent molecules of the substituted imidazolone having different conformations, and one molecule of solvent DMF. The two imidazolone molecules are linked by N—H⋯N and C—H⋯O hydrogen bonds and the DMF is joined to one of these by a N—H⋯O hydrogen bond. Additional N—H⋯N and C—H⋯O hydrogen bonds link these groups into corrugated layers parallel to the (101) plane with the layers joined by C—H⋯π (ring) interactions.</div></div><div><div>The asymmetric unit of the title structure, 2C18H18N4O2·C3H7NO, consists of two independent molecules of the substituted imidazolone having different conformations, and one molecule of solvent DMF. The two imidazolone molecules are linked by N—H⋯N and C—H⋯O hydrogen bonds and the DMF is joined to one of these by an N—H⋯O hydrogen bond. Additional N—H⋯N and C—H⋯O hydrogen bonds link these groups into corrugated layers parallel to the (101) plane with the layers joined by C—H⋯π (ring) interactions. A Hirshfeld surface analysis indicated that H⋯H interactions account for over half of the intermolecular contacts.</div></div>","PeriodicalId":7367,"journal":{"name":"Acta Crystallographica Section E: Crystallographic Communications","volume":"81 2","pages":"Pages 109-113"},"PeriodicalIF":0.5,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11799784/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143381550","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis and crystal structures of 4,4′-methylenebis(2,6-diethylaniline) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline)

IF 0.5 Q4 CRYSTALLOGRAPHY

Acta Crystallographica Section E: Crystallographic Communications

Pub Date : 2025-02-01 DOI: 10.1107/S2056989025000234

Daniil E. Smirnov , Oleg S. Morozov , Ekaterina S. Afanasyeva , Viktor V. Avdeev

Epoxy curers 4,4′-methylenebis(2,6-diethylaniline) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline) were prepared and studied by ¹H NMR and single-crystal X-ray analysis.

The title compounds 4,4′-methylenebis(2,6-diethylaniline) (C₂₁H₃₀N₂, 1) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline) (C₂₁H₂₈Cl₂N₂, 2) are of significant interest as curing agents for a wide range of resins and as building blocks for sterically demanding compounds in the synthesis of ligands for catalysis. This paper describes their synthesis and the preparation of single crystals, with their structures determined through single-crystal X-ray analysis. The presence of the chlorine substituent slightly affects the twist angle between the two aromatic components. The molecules of compound 1 form a network structure through intermolecular N—H⋯N bonds and C—H⋯π interactions, while in the crystal structure of compound 2, the molecules are assembled solely through N—H⋯π interactions. Consequently, despite their chemical similarity, it is the precise structural data that enables us to explain their differing reactivity and opens up the possibility of evaluating steric properties for the development of new materials and ligands.

{"title":"Synthesis and crystal structures of 4,4′-methylenebis(2,6-diethylaniline) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline)","authors":"Daniil E. Smirnov , Oleg S. Morozov , Ekaterina S. Afanasyeva , Viktor V. Avdeev","doi":"10.1107/S2056989025000234","DOIUrl":"10.1107/S2056989025000234","url":null,"abstract":"<div><div>Epoxy curers 4,4′-methylenebis(2,6-diethylaniline) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline) were prepared and studied by 1H NMR and single-crystal X-ray analysis.</div></div><div><div>The title compounds 4,4′-methylenebis(2,6-diethylaniline) (C21H30N2, 1) and 4,4′-methylenebis(3-chloro-2,6-diethylaniline) (C21H28Cl2N2, 2) are of significant interest as curing agents for a wide range of resins and as building blocks for sterically demanding compounds in the synthesis of ligands for catalysis. This paper describes their synthesis and the preparation of single crystals, with their structures determined through single-crystal X-ray analysis. The presence of the chlorine substituent slightly affects the twist angle between the two aromatic components. The molecules of compound 1 form a network structure through intermolecular N—H⋯N bonds and C—H⋯π interactions, while in the crystal structure of compound 2, the molecules are assembled solely through N—H⋯π interactions. Consequently, despite their chemical similarity, it is the precise structural data that enables us to explain their differing reactivity and opens up the possibility of evaluating steric properties for the development of new materials and ligands.</div></div>","PeriodicalId":7367,"journal":{"name":"Acta Crystallographica Section E: Crystallographic Communications","volume":"81 2","pages":"Pages 148-152"},"PeriodicalIF":0.5,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11799795/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143381548","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Crystal structure and Hirshfeld surface analysis of a new polymorph of chloridobis(1,10-phenanthroline-κ2N,N′)copper(II) perchlorate

IF 0.5 Q4 CRYSTALLOGRAPHY

Acta Crystallographica Section E: Crystallographic Communications

Pub Date : 2025-02-01 DOI: 10.1107/S2056989025000209

Maksym O. Plutenko , Oleksandr S. Vynohradov , Matti Haukka , Irina A. Golenya , Snizhana V. Gaidai

Structure analysis of the title compound revealed a second polymorph (space group C2/c, Z = 4) with composition [CuCl(C₁₂H₈N₂)₂]⁺ClO₄⁻. Both the cation and anion in this polymorph exhibit point group symmetry 2.

The title salt (systematic name: 2-methyl-4-oxo-3,4-dihydroquinazolin-1-ium chloride), [CuCl(C₁₂H₈N₂)₂](ClO₄), is comprised of a mononuclear complex cation [Cu(phen)₂Cl]⁺ (phen is 1,10-phenanthroline) and a perchlorate anion, ClO₄⁻, both with point group symmetry 2. The Cu^II atom has a slightly distorted trigonal–bipyramidal coordination environment, defined by a N₄Cl coordination set with the Cl atom and two N atoms at the equatorial sites. In the crystal, each phen ring is parallel to neighboring phen rings. The resulting significant π–π stacking interactions lead to zigzag chains extending parallel to [001]. Hirshfeld surface analysis suggests that the most important contributions to the surface contacts are from H⋯H (32.1%), H⋯C/C⋯H (18.2%), H⋯O/O⋯H (14.6%), H⋯Cl/Cl⋯H (12.7%) and C⋯C (10.6%) interactions.

{"title":"Crystal structure and Hirshfeld surface analysis of a new polymorph of chloridobis(1,10-phenanthroline-κ2N,N′)copper(II) perchlorate","authors":"Maksym O. Plutenko , Oleksandr S. Vynohradov , Matti Haukka , Irina A. Golenya , Snizhana V. Gaidai","doi":"10.1107/S2056989025000209","DOIUrl":"10.1107/S2056989025000209","url":null,"abstract":"<div><div>Structure analysis of the title compound revealed a second polymorph (space group C2/c, Z = 4) with composition [CuCl(C12H8N2)2]+ClO4−. Both the cation and anion in this polymorph exhibit point group symmetry 2.</div></div><div><div>The title salt (systematic name: 2-methyl-4-oxo-3,4-dihydroquinazolin-1-ium chloride), [CuCl(C12H8N2)2](ClO4), is comprised of a mononuclear complex cation [Cu(phen)2Cl]+ (phen is 1,10-phenanthroline) and a perchlorate anion, ClO4−, both with point group symmetry 2. The CuII atom has a slightly distorted trigonal–bipyramidal coordination environment, defined by a N4Cl coordination set with the Cl atom and two N atoms at the equatorial sites. In the crystal, each phen ring is parallel to neighboring phen rings. The resulting significant π–π stacking interactions lead to zigzag chains extending parallel to [001]. Hirshfeld surface analysis suggests that the most important contributions to the surface contacts are from H⋯H (32.1%), H⋯C/C⋯H (18.2%), H⋯O/O⋯H (14.6%), H⋯Cl/Cl⋯H (12.7%) and C⋯C (10.6%) interactions.</div></div>","PeriodicalId":7367,"journal":{"name":"Acta Crystallographica Section E: Crystallographic Communications","volume":"81 2","pages":"Pages 140-143"},"PeriodicalIF":0.5,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11799794/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143381459","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis and crystal structure of 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate

IF 0.5 Q4 CRYSTALLOGRAPHY

Acta Crystallographica Section E: Crystallographic Communications

Pub Date : 2025-02-01 DOI: 10.1107/S2056989025000441

J. Voss , H.G. Stammler , N. Sewald

A 3,6-disubstituted 1,2,4,5-tetrazine was synthesized and characterized by single-crystal X-ray diffraction, revealing a complex hydrogen-bonded network with interactions between tetrazine N atoms and hydroxyl groups, thereby complementing the only scarcely explored features of tetrazines in the solid state.

An orthogonally addressable 3,6-disubstituted 1,2,4,5-tetrazine, namely 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate (C₁₄H₁₄Cl₃N₅O₃), was synthesized and characterized by single-crystal X-ray diffraction. The tetrazine comprises a free hydroxyl and a 2,2,2-trichloroethoxycarbonyl protected amino group, which gives rise to hydrogen-bonding interactions each making the tetrazine highly linked in the solid state. The carbamate moieties form intermolecular hydrogen bonds, stacking the tetrazine molecules above each other, while lateral hydrogen bonds are formed between a tetrazine N atom and a hydroxyl group, the latter interaction being a scarcely explored structural feature of 1,2,4,5-tetrazines.

{"title":"Synthesis and crystal structure of 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate","authors":"J. Voss , H.G. Stammler , N. Sewald","doi":"10.1107/S2056989025000441","DOIUrl":"10.1107/S2056989025000441","url":null,"abstract":"<div><div>A 3,6-disubstituted 1,2,4,5-tetrazine was synthesized and characterized by single-crystal X-ray diffraction, revealing a complex hydrogen-bonded network with interactions between tetrazine N atoms and hydroxyl groups, thereby complementing the only scarcely explored features of tetrazines in the solid state.</div></div><div><div>An orthogonally addressable 3,6-disubstituted 1,2,4,5-tetrazine, namely 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate (C14H14Cl3N5O3), was synthesized and characterized by single-crystal X-ray diffraction. The tetrazine comprises a free hydroxyl and a 2,2,2-trichloroethoxycarbonyl protected amino group, which gives rise to hydrogen-bonding interactions each making the tetrazine highly linked in the solid state. The carbamate moieties form intermolecular hydrogen bonds, stacking the tetrazine molecules above each other, while lateral hydrogen bonds are formed between a tetrazine N atom and a hydroxyl group, the latter interaction being a scarcely explored structural feature of 1,2,4,5-tetrazines.</div></div>","PeriodicalId":7367,"journal":{"name":"Acta Crystallographica Section E: Crystallographic Communications","volume":"81 2","pages":"Pages 164-168"},"PeriodicalIF":0.5,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11799789/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143381544","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Synthesis and crystal structure analysis of 1-ethyl-1,3-dihydro-2H-benzo[d]imidazole-2-thione

IF 0.5 Q4 CRYSTALLOGRAPHY

Acta Crystallographica Section E: Crystallographic Communications

Pub Date : 2025-02-01 DOI: 10.1107/S2056989025000519

Atash V. Gurbanov , Firudin I. Guseinov , Aida I. Samigullina , Tuncer Hökelek , Khudayar I. Hasanov , Tahir A. Javadzade , Alebel N. Belay

Molecules of 1-ethyl-1,3-dihydro-2H-benzo[d]imidazole-2-thione are almost planar. In the crystal, intermolecular N—H⋯S hydrogen bonds link the molecules into pseudocentrosymmetric dimers. N—H⋯S hydrogen bonds, π–π interactions and a weak C—H⋯π(ring) interaction are effective in the stabilization of the crystal structure.

The asymmetric unit of the title compound, C₉H₁₀N₂S, contains two crystallographically independent, almost planar, molecules. In the crystal, intermolecular N—H⋯S hydrogen bonds link the molecules into pseudocentrosymmetric dimers, enclosing R₂²(8) ring motifs. There are mutual π–π interactions between the five- and six-membered rings of each independent molecule in the chosen asymmetric unit, with ring centroid-to-centroid distances of 3.6685 (12) and 3.7062 (12) Å. A weak C—H⋯π(ring) interaction is also observed. The N—H⋯S hydrogen bonds, the π–π interactions and the weak C—H⋯π(ring) interaction are effective in the stabilization of the crystal structure. The structure was refined as an inversion twin with a component occupancy ratio of 0.546 (15):0.454 (16).

{"title":"Synthesis and crystal structure analysis of 1-ethyl-1,3-dihydro-2H-benzo[d]imidazole-2-thione","authors":"Atash V. Gurbanov , Firudin I. Guseinov , Aida I. Samigullina , Tuncer Hökelek , Khudayar I. Hasanov , Tahir A. Javadzade , Alebel N. Belay","doi":"10.1107/S2056989025000519","DOIUrl":"10.1107/S2056989025000519","url":null,"abstract":"<div><div>Molecules of 1-ethyl-1,3-dihydro-2H-benzo[d]imidazole-2-thione are almost planar. In the crystal, intermolecular N—H⋯S hydrogen bonds link the molecules into pseudocentrosymmetric dimers. N—H⋯S hydrogen bonds, π–π interactions and a weak C—H⋯π(ring) interaction are effective in the stabilization of the crystal structure.</div></div><div><div>The asymmetric unit of the title compound, C9H10N2S, contains two crystallographically independent, almost planar, molecules. In the crystal, intermolecular N—H⋯S hydrogen bonds link the molecules into pseudocentrosymmetric dimers, enclosing R22(8) ring motifs. There are mutual π–π interactions between the five- and six-membered rings of each independent molecule in the chosen asymmetric unit, with ring centroid-to-centroid distances of 3.6685 (12) and 3.7062 (12) Å. A weak C—H⋯π(ring) interaction is also observed. The N—H⋯S hydrogen bonds, the π–π interactions and the weak C—H⋯π(ring) interaction are effective in the stabilization of the crystal structure. The structure was refined as an inversion twin with a component occupancy ratio of 0.546 (15):0.454 (16).</div></div>","PeriodicalId":7367,"journal":{"name":"Acta Crystallographica Section E: Crystallographic Communications","volume":"81 2","pages":"Pages 169-171"},"PeriodicalIF":0.5,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11799793/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143381428","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Crystal structure and Hirshfeld surface analysis of 2-methylquinazolin-4(3H)-one hydrochloride

IF 0.5 Q4 CRYSTALLOGRAPHY

Acta Crystallographica Section E: Crystallographic Communications

Pub Date : 2025-02-01 DOI: 10.1107/S2056989025000258

Muzaffar Davlatboev , Sevara Allabergenova , Fazliddin Zulpanov , Ubaydullo Yakubov , Akmaljon Tojiboev , Tulkinjon Sattarov

The quinazolinium moiety of the organic cation is located about a mirror plane. In the crystal, individual cations are linked into [010] zigzag chains by N—H⋯Cl hydrogen-bonding interactions.

The title salt (systematic name: 2-methyl-4-oxo-3,4-dihydroquinazolin-1-ium chloride), C₉H₉N₂O⁺·Cl⁻, has orthorhombic (Pbcm) symmetry. Except for two methyl H atoms, all atoms of the molecular cation are located about a mirror plane, making the quinazolinium moiety exactly planar. Individual molecules are arranged in (001) layers in the crystal. Supramolecular features include N—H⋯Cl hydrogen-bonding interactions, leading to zigzag chains along [010] with D₁¹(2) and C₁²(6) graph-set motifs. Additionally, weak π–π stacking interactions occur between benzene rings in adjacent layers. Hirshfeld surface analysis revealed that the most important contributions to the surface contacts are from H⋯H (36.1%), H⋯C/C⋯H (25.8%), and H⋯O/O⋯H (17.7%) interactions.

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引用次数: 0

Crystal structure of poly[μ3-acetato-diaqua-μ3-sulfato-cerium(III)]: serendipitous synthesis of a layered coordination polymer exhibiting interlayer O—H⋯O hydrogen bonding

IF 0.5 Q4 CRYSTALLOGRAPHY

Acta Crystallographica Section E: Crystallographic Communications

Pub Date : 2025-02-01 DOI: 10.1107/S2056989024012313

Niklas Ruser , Christian Näther , Norbert Stock

In the crystal structure of the title compound, the Ce^III cations are ninefold coordinated and linked into chains via the acetate anions and are further connected into layers by the sulfate dianions.

Single crystals of the title compound, [Ce(CH₃COO)(SO₄)(H₂O)₂]_n, were obtained serendipitously by the reaction of Ce(NO₃)₃·6H₂O with 2,5-thiophenedicarboxylic acid (H₂TDC) and acetic acid in a mixture of ethanol and water, where it is assumed that the sulfate ions leached from the Teflon reactor, which was treated with peroxymonosulfuric acid prior to its use. Its asymmetric unit consists of one Ce^III cation, one sulfate dianion, one acetate anion and two crystallographically independent water molecules, all of them located in general positions. The cerium cations are coordinated by three acetate anions (one O,O-chelating) and three sulfate dianions that are related by symmetry as well as two independent water molecules within an irregular CeO₉ coordination geometry. The Ce^III cations are linked by the acetate ions into [010] chains, which are further connected into (001) layers by the sulfate dianions. Intralayer and interlayer O—H⋯O hydrogen bonds are observed. Powder X-ray diffraction shows that only traces of the title compound have formed together with a large amount of an unknown crystalline phase. Attempts to prepare the title compound in larger amounts and as a pure phase were unsuccessful.

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引用次数: 0

Syntheses and crystal structures of the cerium-based coordination polymers poly[(acetic acid)bis(μ-5-carboxythiophene-2-carboxylato)bis(μ-thiophene-2,5-dicarboxylato)dicerium(III)] and poly[(μ-acetato)aqua(μ4-thiophene-2,5-dicarboxylato)cerium(III)]

IF 0.5 Q4 CRYSTALLOGRAPHY

Acta Crystallographica Section E: Crystallographic Communications

Pub Date : 2025-02-01 DOI: 10.1107/S2056989025000210

Niklas Ruser , Christian Näther , Norbert Stock

In the crystal structures of the title compounds, the Ce^III cations are eightfold coordinated and linked into three-dimensional frameworks by ligands based on different deprotonated derivates of 2,5-thiophenedicarboxylic acid. Both compounds exhibit O—H⋯O hydrogen bonds.

The title compounds, [Ce₂(C₆H₃SO₄)₂(C₆H₂SO₄)₂(CH₃COOH)]_n (1) and [Ce(CH₃COO)(C₆H₂SO₄)(H₂O)]_n (2) were synthesized by solvothermal reaction of Ce(NO₃)₃·6H₂O with 2,5-thiophenedicarboxylic acid (H₂TDC, C₆H₄SO₄) and acetic acid in acetonitrile or ethanol/water, respectively. These compounds were obtained as single crystals among other crystalline phases. Both compounds belong to the family of three-dimensional coordination polymers. The asymmetric unit of 1 consists of two Ce^III cations, two TDC²⁻ dianions, two HTDC⁻ anions and one acetic acid ligand, all of them located in general positions. The two Ce^III cations are each coordinated by eight oxygen atoms in the form of distorted square antiprisms. These are bridged by carboxylate and carboxylic acid groups, forming mono-periodic hybrid inorganic building units (IBUs), which are connected into a three-dimensional network by the TDC²⁻ and HTDC⁻ ligands. Compound 2 has an asymmetric unit composed of one Ce^III cation, one TDC²⁻ dianion, one acetate anion and one water molecule in general positions. The cerium atom is eightfold coordinated by oxygen atoms. Edge-sharing CeO₈ polyhedra form a dinuclear IBU (Ce₂O₁₄). This IBU is bridged by six TDC²⁻ linkers to nine other IBUs, forming a three-dimensional framework. Both title compounds exhibit additional O—H⋯O hydrogen bonds. Powder X-ray diffraction shows that both compounds were not obtained as pure phases.

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引用次数: 0