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Crystal clear: the impact of crystal structure in the development of high-performance organic semiconductors. 晶莹剔透:晶体结构对开发高性能有机半导体的影响。
IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-01 Epub Date: 2024-10-31 DOI: 10.1107/S2053229624010520
Callum J McHugh
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引用次数: 0
Molecular and crystal structures of six poly(arylsulfinyl)- and poly(arylsulfanyl)ferrocenes. 六种聚(芳基亚磺酰基)和聚(芳基硫酰基)二茂铁的分子和晶体结构。
IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-01 Epub Date: 2024-10-04 DOI: 10.1107/S2053229624009318
Tobias Blockhaus, Karlheinz Sünkel

Starting from (p-tolylsulfinyl)ferrocene (1), a mixture of the complete series [CpFe{C5H5-n(SOTol-p)n}] (n = 2-4) (2-4) in all regioisomers was obtained. After chromatographic separation, crystals of 1,2-bis[(4-methylbenzene)sulfinyl]ferrocene, 2a, and 1,3-bis[(4-methylbenzene)sulfinyl]ferrocene, 2b, both [Fe(C5H5)(C19H17O2S2)], as well as of 1,2,3-tris[(4-methylbenzene)sulfinyl]ferrocene, [Fe(C5H5)(C26H23O3S3)], 3a, and 1,2,3,4-tetrakis[(4-methylbenzene)sulfinyl]ferrocene ethyl acetate 0.75-solvate, [Fe(C5H5)(C33H29O4S4)]·0.75C4H8O2, 4, could be isolated. Their molecular and crystal structures are compared with each other and also with the so far unreported structures of related 1,2-bis(phenylsulfanyl)ferrocene, [Fe(C5H5)(C17H13S2)], 5, and 1,2,3,4-tetrakis(phenylsulfanyl)ferrocene, [Fe(C5H5)(C29H21S4)], 6. In all the sulfinyl structures, the O atoms of the S=O groups are in equatorial positions, except for that in tetrasubstituted 4. All the arene rings of these compounds (except for one ring in 4) are in axial positions directed away from the Fe atom, mostly in a near perpendicular orientation with respect to the plane of the cyclopentadienyl ring. The main intermolecular interactions in the crystals are C-H...H-C, C-H...π and C-H...O, while C-H...S interactions are much less important, except for tetrasulfanyl compound 6. π-π interactions (intramolecular) are only important in compound 3a. Hirshfeld analysis shows that dispersion terms are dominant for the interaction energies of all six compounds. In general, the calculated total interaction energies increase with increasing number of substituents and are higher for the sulfinyl than for the sulfanyl groups.

从 (对甲苯亚磺酰基)二茂铁 (1) 开始,得到了一个完整系列 [CpFe{C5H5-n(SOTol-p)n}] (n = 2-4) (2-4) 的混合物,其中包含所有区域异构体。经过色谱分离,得到了 1,2-双[(4-甲基苯)亚磺酰基]二茂铁 2a 和 1,3-双[(4-甲基苯)亚磺酰基]二茂铁 2b 的晶体,它们都是[Fe(C5H5)(C19H17O2S2)]、以及 1,2,3-三[(4-甲基苯)亚磺酰基]二茂铁[Fe(C5H5)(C26H23O3S3)]3a 和 1,2,3,4-四[(4-甲基苯)亚磺酰基]二茂铁乙酸乙酯 0.75 溶剂,即[Fe(C5H5)(C33H29O4S4)]-0.75C4H8O2,4。我们将它们的分子结构和晶体结构相互进行了比较,并与迄今为止尚未报道的相关 1,2-双(苯硫基)二茂铁 [Fe(C5H5)(C17H13S2)], 5 和 1,2,3,4-四(苯硫基)二茂铁 [Fe(C5H5)(C29H21S4)], 6 的结构进行了比较。在所有的亚磺酰基结构中,除四取代基 4 外,S=O 基团的 O 原子都位于赤道位置。这些化合物的所有烯环(除 4 中的一个环外)都位于远离铁原子的轴向位置,大部分与环戊二烯环的平面呈近乎垂直的方向。晶体中主要的分子间相互作用是 C-H...H-C、C-H...π 和 C-H...O,而 C-H...S(除四硫化合物 6 外)的重要性要小得多。Hirshfeld 分析表明,分散项在所有六种化合物的相互作用能中都占主导地位。一般来说,计算得出的总相互作用能随着取代基数目的增加而增加,并且亚磺酰基的相互作用能高于硫酰基。
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引用次数: 0
A salt from biologically active compounds pyridine-2,3-dicarboxylic (quinolinic) acid and cytosine. 一种来自具有生物活性的化合物吡啶-2,3-二羧酸(喹啉酸)和胞嘧啶的盐。
IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-01 Epub Date: 2024-10-11 DOI: 10.1107/S2053229624009598
Olga Książkiewicz

Biologically active compounds are highly sought-after materials for developing novel structures applicable to industry. Cytosine and pyridine-2,3-dicarboxylic acid (quinolinic acid) are notably significant environmentally. Cytosine, a pyrimidine derivative, features a six-membered ring with a ketone and an amino group, constituting a fundamental nitrogenous base found in deoxyribonucleic acid (DNA). The present synthesis yielded a salt of dipyridine-2,3-dicarboxylic acid with cytosine, wherein a proton was transferred from a carboxyl group of quinolinic acid to a ring N atom in the cytosine molecule giving the salt 6-amino-2-oxo-2,3-dihydropyrimidin-1-ium 3-carboxypyridine-2-carboxylate, C4H6N3O+·C7H4NO4-. A Hirshfeld surface analysis was conducted to examine the contribution of contacts within the salt. The structure of the salt was compared to other structures containing quinolinic acid in the Cambridge Structural Database (CSD).

生物活性化合物是开发适用于工业的新型结构的热门材料。胞嘧啶和吡啶-2,3-二羧酸(喹啉酸)在环境中的作用尤为显著。胞嘧啶是一种嘧啶衍生物,具有一个带有酮和氨基的六元环,是脱氧核糖核酸(DNA)中的基本含氮碱基。本合成法得到了二吡啶-2,3-二羧酸与胞嘧啶的盐,其中质子从喹啉酸的羧基转移到胞嘧啶分子中的环 N 原子上,得到了 6-氨基-2-氧代-2,3-二氢嘧啶-1-鎓 3-羧基吡啶-2-羧酸盐 C4H6N3O+-C7H4NO4-。对该盐进行了 Hirshfeld 表面分析,以研究其内部接触的贡献。该盐的结构与剑桥结构数据库(CSD)中含有喹啉酸的其他结构进行了比较。
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引用次数: 0
Synthesis, XRD structural analysis and theoretical studies of a potential inhibitor against rheumatoid arthritis (RA). 一种潜在的类风湿性关节炎(RA)抑制剂的合成、XRD 结构分析和理论研究。
IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-01 Epub Date: 2024-10-24 DOI: 10.1107/S2053229624010106
Kevin Monge-Hoyos, Rodolfo Moreno-Fuquen, Kevin Arango-Daraviña, Javier Ellena, Pedro H O Santiago

This work focused on analyzing the properties of N-(5-nitrothiazol-2-yl)furan-2-carboxamide (C8H5N3O4S, NTFC) as a possible inhibitor of the rheumatoid arthritis process. The synthesis of NTFC was carried out and good-quality crystals were obtained and studied by NMR (1H and 13C), DEPT 135, UV-Vis, IR, MS and single-crystal X-ray diffraction. The structure of NTFC consists of two rings, thiazole and furan, and a central C-N-C(=O)-C segment, which appears to be planar. This central amide segment forms angles of 2.61 (10) and 7.97 (11)° with the planes of the thiazole and furan rings, respectively. The crystal structure of NTFC exhibits N-H...N, N-H...O and C-H...O hydrogen bonds, and C-H...π and π-π interactions that facilitate self-assembly and the formation of hydrogen-bonded dimers, which implies the appearance of R22(8) graph-set motifs in this interaction. The stability of the dimeric unit is complemented by the formation of strong intramolecular C-S...O interactions of chalcogen character, with an S...O distance of 2.6040 (18) Å. Hirshfeld surface (HS) analysis revealed that O...H/H...O interactions were dominant, accounting for 36.8% of the total HS, and that N-H...N interactions were fundamental to the formation of the dimeric structure. The molecular electrostatic potential (MEP) map showed a maximum energy of 46.73 kcal mol-1 and a minimum of -36.06 kcal mol-1. The interaction energies of molecular pairs around NTFC are highest for those interactions linked by N-H hydrogen bonds. The properties of the NTFC ligand as a potential inhibitor of the DHODH (dihydroorotate dehydrogenase) enzyme were evaluated by molecular docking, showing coupling energies very close to those obtained with the control drug for rheumatoid arthritis, i.e. leflunomide.

这项研究的重点是分析 N-(5-硝基噻唑-2-基)呋喃-2-甲酰胺(C8H5N3O4S,NTFC)作为类风湿性关节炎可能的抑制剂的特性。通过核磁共振(1H 和 13C)、DEPT 135、紫外可见光谱、红外光谱、质谱和单晶 X 射线衍射等方法对 NTFC 进行了研究。NTFC 的结构由两个环(噻唑环和呋喃环)和一个看似平面的 C-N-C(=O)-C 中心段组成。该中心酰胺段分别与噻唑环和呋喃环的平面形成 2.61 (10) 和 7.97 (11) ° 的夹角。NTFC 的晶体结构显示出 N-H...N、N-H...O 和 C-H...O 氢键以及 C-H...π 和 π-π 相互作用,这些作用促进了自组装和氢键二聚体的形成,这意味着在这种相互作用中出现了 R22(8) 图集图案。二聚体单元的稳定性还得益于分子内形成的具有缩醛特性的强 C-S...O 相互作用,S...O 间距为 2.6040 (18) Å。Hirshfeld 表面(HS)分析表明,O...H/H...O 相互作用占主导地位,占总 HS 的 36.8%,N-H...N 相互作用是形成二聚结构的基础。分子静电位(MEP)图显示最大能量为 46.73 kcal mol-1,最小为 -36.06 kcal mol-1。通过 N-H 氢键连接的分子对在 NTFC 周围的相互作用能量最高。分子对接评估了 NTFC 配体作为 DHODH(二氢烟酸脱氢酶)潜在抑制剂的特性,结果显示其耦合能与类风湿性关节炎对照药物(来氟米特)非常接近。
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引用次数: 0
Structural insights into supramolecular interactions in isostructural salts of 2,4,6-triaminopyrimidinium with various heterocyclic carboxylates. 2,4,6 三氨基嘧啶与各种杂环羧酸盐等结构盐的超分子相互作用的结构见解。
IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-01 Epub Date: 2024-10-04 DOI: 10.1107/S2053229624008787
Marimuthu Mohana, Sundaramoorthy Gomathi, Packianathan Thomas Muthiah, Ray J Butcher

2,4,6-Triaminopyrimidine is an interesting and challenging molecule due to the presence of multiple hydrogen-bond donors and acceptors. Its noncovalent interactions with a variety of carboxylic acids provide several supramolecular aggregates with frequently occurring molecular synthons. The present work focuses on the supramolecular interactions of 2,4,6-triaminopyrimidinium 3-(indol-3-yl)propionate-3-(indol-3-yl)propionic acid (1/1), C4H8N5+·C11H10NO2-·C11H11NO2, (I), 2,4,6-triaminopyrimidinium 2-(indol-3-yl)acetate, C4H8N5+·C10H8NO2-, (II), 2,4,6-triaminopyrimidinium 5-bromothiophene-2-carboxylate, C4H8N5+·C5H2BrO2S-, (III), and 2,4,6-triaminopyrimidinium 5-chlorothiophene-2-carboxylate, C4H8N5+·C5H2ClO2S-, (IV). All four salts exhibit robust homomeric and heteromeric R22(8) ring motifs. Salts (I) and (II) develop sextuple [in (I)] and quadruple [in (I) and (II)] hydrogen-bonded arrays through fused-ring motifs. Salt (II) exhibits a rosette-like architecture. Salt (IV) is isostructural and isomorphous with salt (III), exhibiting an identical crystal structure with a different composition and an identical supramolecular architecture. In salts (III) and (IV), a linear hetero-tetrameric motif is formed and, in addition, both salts exhibit halogen-π interactions which enhance the crystal stability. All four salts develop a supramolecular hydrogen-bonded pattern facilitated by several N-H...O and N-H...N hydrogen bonds with multiple furcated donors and acceptors.

由于存在多个氢键供体和受体,2,4,6-三氨基嘧啶是一种有趣而具有挑战性的分子。它与多种羧酸的非共价相互作用提供了几种超分子聚合体,并经常出现分子合子。本研究的重点是 2,4,6-三氨基嘧啶鎓 3-(吲哚-3-基)丙酸盐-3-(吲哚-3-基)丙酸 (1/1), C4H8N5+-C11H10NO2--C11H11NO2, (I), 2,4,6-三氨基嘧啶鎓 2-(吲哚-3-基)乙酸盐的超分子相互作用、C4H8N5+-C10H8NO2-,(II)、2,4,6-三氨基嘧啶鎓 5-溴噻吩-2-羧酸盐,C4H8N5+-C5H2BrO2S-,(III)和 2,4,6-三氨基嘧啶鎓 5-氯噻吩-2-羧酸盐,C4H8N5+-C5H2ClO2S-,(IV)。所有四种盐都表现出强大的同构和异构 R22(8) 环图案。盐 (I) 和盐 (II) 通过融合环图案形成六重 [在盐 (I) 中] 和四重 [在盐 (I) 和盐 (II) 中] 氢键阵列。盐 (II) 呈莲座状结构。盐(IV)与盐(III)是同构异构体,晶体结构相同,但组成不同,超分子结构也相同。在盐(III)和盐(IV)中,形成了线性杂四聚体图案,此外,这两种盐还表现出卤素-π相互作用,从而提高了晶体的稳定性。所有四种盐都形成了一种超分子氢键模式,由多个 N-H...O 和 N-H...N氢键以及多个呋喃供体和受体促成。
{"title":"Structural insights into supramolecular interactions in isostructural salts of 2,4,6-triaminopyrimidinium with various heterocyclic carboxylates.","authors":"Marimuthu Mohana, Sundaramoorthy Gomathi, Packianathan Thomas Muthiah, Ray J Butcher","doi":"10.1107/S2053229624008787","DOIUrl":"10.1107/S2053229624008787","url":null,"abstract":"<p><p>2,4,6-Triaminopyrimidine is an interesting and challenging molecule due to the presence of multiple hydrogen-bond donors and acceptors. Its noncovalent interactions with a variety of carboxylic acids provide several supramolecular aggregates with frequently occurring molecular synthons. The present work focuses on the supramolecular interactions of 2,4,6-triaminopyrimidinium 3-(indol-3-yl)propionate-3-(indol-3-yl)propionic acid (1/1), C<sub>4</sub>H<sub>8</sub>N<sub>5</sub><sup>+</sup>·C<sub>11</sub>H<sub>10</sub>NO<sub>2</sub><sup>-</sup>·C<sub>11</sub>H<sub>11</sub>NO<sub>2</sub>, (I), 2,4,6-triaminopyrimidinium 2-(indol-3-yl)acetate, C<sub>4</sub>H<sub>8</sub>N<sub>5</sub><sup>+</sup>·C<sub>10</sub>H<sub>8</sub>NO<sub>2</sub><sup>-</sup>, (II), 2,4,6-triaminopyrimidinium 5-bromothiophene-2-carboxylate, C<sub>4</sub>H<sub>8</sub>N<sub>5</sub><sup>+</sup>·C<sub>5</sub>H<sub>2</sub>BrO<sub>2</sub>S<sup>-</sup>, (III), and 2,4,6-triaminopyrimidinium 5-chlorothiophene-2-carboxylate, C<sub>4</sub>H<sub>8</sub>N<sub>5</sub><sup>+</sup>·C<sub>5</sub>H<sub>2</sub>ClO<sub>2</sub>S<sup>-</sup>, (IV). All four salts exhibit robust homomeric and heteromeric R<sub>2</sub><sup>2</sup>(8) ring motifs. Salts (I) and (II) develop sextuple [in (I)] and quadruple [in (I) and (II)] hydrogen-bonded arrays through fused-ring motifs. Salt (II) exhibits a rosette-like architecture. Salt (IV) is isostructural and isomorphous with salt (III), exhibiting an identical crystal structure with a different composition and an identical supramolecular architecture. In salts (III) and (IV), a linear hetero-tetrameric motif is formed and, in addition, both salts exhibit halogen-π interactions which enhance the crystal stability. All four salts develop a supramolecular hydrogen-bonded pattern facilitated by several N-H...O and N-H...N hydrogen bonds with multiple furcated donors and acceptors.</p>","PeriodicalId":7115,"journal":{"name":"Acta Crystallographica Section C Structural Chemistry","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142370719","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Structural comparison of [Ce(OtBu)Cl(THF)5](BPh4) to smaller rare earth analogues. [Ce(OtBu)Cl(THF)5](BPh4)与较小的稀土类似物的结构比较。
IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-01 Epub Date: 2024-10-28 DOI: 10.1107/S2053229624009872
Jarrod R Thomas, Kavisha A Sarma, Marcus J Giansiracusa, Scott A Sulway

The introduction of the cerium(III) analogue (1-Ce, Ln = Ce) of (tert-butoxido)chloridopentakis(tetrahydrofuran)lanthanide(III) tetraphenylborate tetrahydrofuran disolvate, [Ln{OC(CH3)3}Cl(C4H8O)5][B(C6H5)4]·2C4H8O or [Ln(OtBu)Cl(THF)5](BPh4)·2THF (1-Ln) has been achieved with a structural comparison between the existing solid-state structures of other rare earth analogues and the title compound at 100 and 180 K. The cation in 1-Ce is targeted as the cerium(III) ion possesses the criteria to exhibit slow magnetic relaxation in axial point-charge crystal fields, akin to the dysprosium(III) ion in 1-Dy. AC magnetic susceptibility experiments reveal no such behaviour for 1-Ce, putting the viability of cerium-based SMMs into question.

引入(叔丁氧羰基)氯戊二(四氢呋喃)镧系元素(III)四苯基硼酸四氢呋喃二醇酯的铈(III)类似物(1-Ce,Ln = Ce)、[Ln{OC(CH3)3}Cl(C4H8O)5][B(C6H5)4]-2C4H8O 或 [Ln(OtBu)Cl(THF)5](BPh4)-2THF(1-Ln)。1-Ce 中的阳离子是目标化合物,因为铈(III)离子具有在轴向点电荷晶体场中表现出缓慢磁弛豫的标准,类似于 1-Dy 中的镝(III)离子。交流磁感应强度实验显示 1-Ce 没有这种行为,这使得铈基 SMM 的可行性受到质疑。
{"title":"Structural comparison of [Ce(O<sup>t</sup>Bu)Cl(THF)<sub>5</sub>](BPh<sub>4</sub>) to smaller rare earth analogues.","authors":"Jarrod R Thomas, Kavisha A Sarma, Marcus J Giansiracusa, Scott A Sulway","doi":"10.1107/S2053229624009872","DOIUrl":"10.1107/S2053229624009872","url":null,"abstract":"<p><p>The introduction of the cerium(III) analogue (1-Ce, Ln = Ce) of (tert-butoxido)chloridopentakis(tetrahydrofuran)lanthanide(III) tetraphenylborate tetrahydrofuran disolvate, [Ln{OC(CH<sub>3</sub>)<sub>3</sub>}Cl(C<sub>4</sub>H<sub>8</sub>O)<sub>5</sub>][B(C<sub>6</sub>H<sub>5</sub>)<sub>4</sub>]·2C<sub>4</sub>H<sub>8</sub>O or [Ln(O<sup>t</sup>Bu)Cl(THF)<sub>5</sub>](BPh<sub>4</sub>)·2THF (1-Ln) has been achieved with a structural comparison between the existing solid-state structures of other rare earth analogues and the title compound at 100 and 180 K. The cation in 1-Ce is targeted as the cerium(III) ion possesses the criteria to exhibit slow magnetic relaxation in axial point-charge crystal fields, akin to the dysprosium(III) ion in 1-Dy. AC magnetic susceptibility experiments reveal no such behaviour for 1-Ce, putting the viability of cerium-based SMMs into question.</p>","PeriodicalId":7115,"journal":{"name":"Acta Crystallographica Section C Structural Chemistry","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142492702","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Hydrogen-bonding interactions in the salts 2,4,6-triaminopyrimidin-1-ium sorbate dihydrate, 2,4,6-triaminopyrimidin-1-ium N-phenylantharanilate and 2,4,6-triaminopyrimidin-1-ium p-toluenesulfonate. 2,4,6-三氨基嘧啶-1-鎓山梨酸盐二水物、2,4,6-三氨基嘧啶-1-鎓 N-苯基镧酸盐和 2,4,6-三氨基嘧啶-1-鎓对甲苯磺酸盐中的氢键相互作用。
IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-01 Epub Date: 2024-10-04 DOI: 10.1107/S2053229624008763
Marimuthu Mohana, Sundaramoorthy Gomathi, Packianathan Thomas Muthiah, Ray J Butcher

Three salts, namely, 2,4,6-triaminopyrimidin-1-ium sorbate dihydrate, C4H8N5+·C6H7O2-·2H2O, (I), 2,4,6-triaminopyrimidin-1-ium N-phenylanthranilate, C4H8N5+·C13H10NO2-, (II), and 2,4,6-triaminopyrimidin-1-ium p-toluenesulfonate, C4H8N5+·C7H7O3S-, (III), were synthesized, characterized by X-ray diffraction techniques and their supramolecular interactions investigated. In all three crystal structures, protonation of the pyrimidine moiety occurs at the N1 position and is reflected in a widening of the C-N-C bond angle. In salts (I)-(III), the primary acid-base interaction occurs through a pair of N-H...O hydrogen bonds to give a heterodimeric R22(8) synthon. Salts (II) and (III) form a discrete centrosymmetric base pair that produces a homodimeric R22(8) synthon and salt (I) forms a water-mediated base pair resulting in a tetrameric R44(12) synthon. The supramolecular patterns exhibited by sulfonate salt (III) mimic the patterns of carboxylate salt (II) and both exhibit a DADA array (D = donor and A = acceptor) quadruple hydrogen-bonded pattern. The crystal structures of salts (I) and (III) are stabilized by offset and face-to-face aromatic π-π stacking interactions, respectively. The resulting architectures in salts (I)-(III) are a supramolecular sheet with a rosette-like architecture in (I), a supramolecular sheet-like architecture in (II) and a three-dimensional supramolecular network in (III).

合成了三种盐,即 2,4,6-三氨基嘧啶-1-鎓山梨酸盐二水物 C4H8N5+-C6H7O2--2H2O(I)、2,4,6-三氨基嘧啶-1-鎓 N-苯基苋酸酯 C4H8N5+-C13H10NO2-(II)和 2,4,6-三氨基嘧啶-1-鎓对甲苯磺酸盐 C4H8N5+-C7H7O3S-(III)、合成了 6-三氨基嘧啶-1-鎓对甲苯磺酸盐(C4H8N5+-C7H7O3S-,(III)),并利用 X 射线衍射技术对其进行了表征和超分子相互作用研究。在所有三种晶体结构中,嘧啶分子的质子化都发生在 N1 位置,并反映在 C-N-C 键角的扩大上。在盐(I)-(III)中,主要的酸碱相互作用是通过一对 N-H...O氢键发生的,从而产生一个异源的 R22(8)合子。盐(II)和(III)形成了离散的中心对称碱基对,产生了同源的 R22(8),盐(I)形成了水介导的碱基对,产生了四聚体的 R44(12)。磺酸盐(III)显示的超分子模式与羧酸盐(II)的模式相似,都显示出 DADA 阵列(D = 供体,A = 受体)四重氢键模式。盐(I)和盐(III)的晶体结构分别通过偏移和面对面的芳香族 π-π 堆积相互作用得到稳定。盐(I)-(III)的晶体结构分别为(I)中的莲座状超分子片状结构、(II)中的超分子片状结构和(III)中的三维超分子网络结构。
{"title":"Hydrogen-bonding interactions in the salts 2,4,6-triaminopyrimidin-1-ium sorbate dihydrate, 2,4,6-triaminopyrimidin-1-ium N-phenylantharanilate and 2,4,6-triaminopyrimidin-1-ium p-toluenesulfonate.","authors":"Marimuthu Mohana, Sundaramoorthy Gomathi, Packianathan Thomas Muthiah, Ray J Butcher","doi":"10.1107/S2053229624008763","DOIUrl":"10.1107/S2053229624008763","url":null,"abstract":"<p><p>Three salts, namely, 2,4,6-triaminopyrimidin-1-ium sorbate dihydrate, C<sub>4</sub>H<sub>8</sub>N<sub>5</sub><sup>+</sup>·C<sub>6</sub>H<sub>7</sub>O<sub>2</sub><sup>-</sup>·2H<sub>2</sub>O, (I), 2,4,6-triaminopyrimidin-1-ium N-phenylanthranilate, C<sub>4</sub>H<sub>8</sub>N<sub>5</sub><sup>+</sup>·C<sub>13</sub>H<sub>10</sub>NO<sub>2</sub><sup>-</sup>, (II), and 2,4,6-triaminopyrimidin-1-ium p-toluenesulfonate, C<sub>4</sub>H<sub>8</sub>N<sub>5</sub><sup>+</sup>·C<sub>7</sub>H<sub>7</sub>O<sub>3</sub>S<sup>-</sup>, (III), were synthesized, characterized by X-ray diffraction techniques and their supramolecular interactions investigated. In all three crystal structures, protonation of the pyrimidine moiety occurs at the N1 position and is reflected in a widening of the C-N-C bond angle. In salts (I)-(III), the primary acid-base interaction occurs through a pair of N-H...O hydrogen bonds to give a heterodimeric R<sub>2</sub><sup>2</sup>(8) synthon. Salts (II) and (III) form a discrete centrosymmetric base pair that produces a homodimeric R<sub>2</sub><sup>2</sup>(8) synthon and salt (I) forms a water-mediated base pair resulting in a tetrameric R<sub>4</sub><sup>4</sup>(12) synthon. The supramolecular patterns exhibited by sulfonate salt (III) mimic the patterns of carboxylate salt (II) and both exhibit a DADA array (D = donor and A = acceptor) quadruple hydrogen-bonded pattern. The crystal structures of salts (I) and (III) are stabilized by offset and face-to-face aromatic π-π stacking interactions, respectively. The resulting architectures in salts (I)-(III) are a supramolecular sheet with a rosette-like architecture in (I), a supramolecular sheet-like architecture in (II) and a three-dimensional supramolecular network in (III).</p>","PeriodicalId":7115,"journal":{"name":"Acta Crystallographica Section C Structural Chemistry","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142370717","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photocrystallography - common or exclusive? 光晶体学--通用还是专用?
IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-01 Epub Date: 2024-10-07 DOI: 10.1107/S2053229624009690
Katarzyna N Jarzembska
{"title":"Photocrystallography - common or exclusive?","authors":"Katarzyna N Jarzembska","doi":"10.1107/S2053229624009690","DOIUrl":"10.1107/S2053229624009690","url":null,"abstract":"","PeriodicalId":7115,"journal":{"name":"Acta Crystallographica Section C Structural Chemistry","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142379859","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Dinuclear zinc(II) acetate complexes derived from N,N',S-tridentate Schiff bases: synthesis, structural study and Hirshfeld surface analysis. 源自 N,N',S-三叉戟席夫碱的双核醋酸锌(II)配合物:合成、结构研究和希尔斯菲尔德表面分析。
IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-01 Epub Date: 2024-10-04 DOI: 10.1107/S205322962400946X
Odalys Anaya-Avila, Oscar Muñoz-Granados, Noemí Andrade-López, José G Alvarado-Rodríguez, Diego Martínez-Otero

Three dinuclear zinc(II) acetate complexes of the general formula [Zn{Ln}(AcO)]2, namely, di-μ-acetato-κ4O:O'-bis[({2-[(pyridin-2-ylmethylidene)amino]phenyl}sulfanido-κ3N,N',S)zinc(II)], [Zn2(C12H9N2S)2(C2H3O2)2] (n = 1), 4, μ-acetato-1:2κ2O:O'-acetato-2κO-[μ-(2-{[1-(pyridin-2-yl)ethylidene]amino}phenyl)sulfanido-1κS:2κ3N,N',S][(2-{[1-(pyridin-2-yl)ethylidene]amino}phenyl)sulfanido-1κ3N,N',S]dizinc(II), [Zn2(C13H11N2S)2(C2H3O2)2] (n = 2), 5, and μ-acetato-1:2κ2O:O'-acetato-2κO-[μ-(2-{[phenyl(pyridin-2-yl)methylidene]amino}phenyl)sulfanido-1κS:2κ3N,N',S][(2-{[phenyl(pyridin-2-yl)methylidene]amino}phenyl)sulfanido-1κ3N,N',S]dizinc(II)-bis(2-aminophenyl) disulfide (2/1), [Zn2(C18H13N2S)2(C2H3O2)2]·0.5C12H12N2S2 (n = 3), 6·0.5(2-APS)2, were obtained from the reaction of 2-R-(pyridin-2-yl)benzothiazoline precursors (R = H, 1; R = Me, 2; R = Ph, 3) with zinc acetate dihydrate in a 1:1 ratio. All the complexes crystallized as dinuclear species and complex 6 cocrystallized with one molecule of bis(2-aminophenyl) disulfide (2-APS)2. The anionic Schiff base ligands {Ln}- displayed a κ2N,κS-tridentate coordination mode with the formation of two five-membered chelate rings. In 4, 5 and 6·0.5(2-APS)2, both ZnII ions are pentacoordinated and the coordination sphere of 4 was different with respect to those in 5 and 6·0.5(2-APS)2. For 4, the X-ray diffraction study showed a dinuclear complex containing two bridging acetate ligands linked to both ZnII ions. For 5 and 6·0.5(2-APS)2, the dinuclear complexes displayed one bridging acetate ligand linked to both ZnII ions, where the first ZnII ion includes a dative bond with one S atom from an adjacent anionic Schiff base {Ln}-, while the second ZnII ion is coordinated to one terminal acetate ligand. In each dinuclear complex, the geometry is the same for both ZnII metal centres. The local geometry of the ZnII cation in 4 is halfway between trigonal bipyramidal and square pyramidal local geometries; in 5 and 6, the local geometries are described as distorted square pyramidal. Hirshfeld surface analysis of 5 and 6 showed the predominance of H...H interactions, as well as the contribution of C-H...C, C-H...O and C-H...S noncovalent interactions to the cohesion of the crystalline network of the ZnII complexes.

三种通式为[Zn{Ln}(AcO)]2 的双核醋酸锌(II)配合物,即二μ-醋酸基-κ4O:O'-双[({2-[(吡啶-2-基亚甲基)氨基]苯基}硫代-κ3N,N',S)锌(II)],[Zn2(C12H9N2S)2(C2H3O2)2](n = 1),4,μ-乙酰基-1:2κO:O'-乙酰基-2κO-[μ-(2-{[1-(吡啶-2-基)亚乙基]氨基}苯基)硫-1κS:2κ3N,N',S][(2-{[1-(吡啶-2-基)亚乙基]氨基}苯基)硫代-1κ3N,N',S]二锌(II),[Zn2(C13H11N2S)2(C2H3O2)2](n = 2),5,和μ-乙酰基-1:2κ2O:O'-acetato-2κO-[μ-(2-{[phenyl(pyridin-2-yl)methylidene]amino}phenyl)sulfanido-1κS:2κ3N,N',S][(2-{[苯基(吡啶-2-基)亚甲基]氨基}苯基)磺酰-1κ3N,N',S]二锌(II)-双(2-氨基苯基)二硫化物 (2/1),[Zn2(C18H13N2S)2(C2H3O2)2]-0。5C12H12N2S2 (n = 3)、6-0.5(2-APS)2 是由 2-R-(吡啶-2-基)苯并噻唑啉前体(R = H,1;R = Me,2;R = Ph,3)与二水醋酸锌按 1:1 的比例反应得到的。所有配合物均以双核形式结晶,配合物 6 与一分子双(2-氨基苯基)二硫化物(2-APS)2 共同结晶。阴离子席夫碱配体 {Ln}- 显示出一种 κ2N、κS-三叉配位模式,形成两个五元螯合环。在 4、5 和 6-0.5(2-APS)2 中,两个 ZnII 离子都是五配位的,而且 4 的配位球与 5 和 6-0.5(2-APS)2 中的配位球不同。X 射线衍射研究显示,4 是一种双核配合物,含有两个与两个 ZnII 离子相连的桥接醋酸配体。对于 5 和 6-0.5(2-APS)2,双核配合物显示了一个与两个 ZnII 离子相连的桥接醋酸配体,其中第一个 ZnII 离子与相邻阴离子席夫碱 {Ln}- 的一个 S 原子形成配位键,而第二个 ZnII 离子则与一个末端醋酸配体配位。在每个双核复合物中,两个 ZnII 金属中心的几何形状相同。在 4 中,ZnII 阳离子的局部几何形状介于三叉双锥和方形金字塔局部几何形状之间;在 5 和 6 中,局部几何形状被描述为扭曲的方形金字塔。对 5 和 6 的 Hirshfeld 表面分析表明,H...H 相互作用以及 C-H...C、C-H...O 和 C-H...S 非共价相互作用对 ZnII 复合物晶体网络的内聚力起着主导作用。
{"title":"Dinuclear zinc(II) acetate complexes derived from N,N',S-tridentate Schiff bases: synthesis, structural study and Hirshfeld surface analysis.","authors":"Odalys Anaya-Avila, Oscar Muñoz-Granados, Noemí Andrade-López, José G Alvarado-Rodríguez, Diego Martínez-Otero","doi":"10.1107/S205322962400946X","DOIUrl":"10.1107/S205322962400946X","url":null,"abstract":"<p><p>Three dinuclear zinc(II) acetate complexes of the general formula [Zn{L<sup>n</sup>}(AcO)]<sub>2</sub>, namely, di-μ-acetato-κ<sup>4</sup>O:O'-bis[({2-[(pyridin-2-ylmethylidene)amino]phenyl}sulfanido-κ<sup>3</sup>N,N',S)zinc(II)], [Zn<sub>2</sub>(C<sub>12</sub>H<sub>9</sub>N<sub>2</sub>S)<sub>2</sub>(C<sub>2</sub>H<sub>3</sub>O<sub>2</sub>)<sub>2</sub>] (n = 1), 4, μ-acetato-1:2κ<sup>2</sup>O:O'-acetato-2κO-[μ-(2-{[1-(pyridin-2-yl)ethylidene]amino}phenyl)sulfanido-1κS:2κ<sup>3</sup>N,N',S][(2-{[1-(pyridin-2-yl)ethylidene]amino}phenyl)sulfanido-1κ<sup>3</sup>N,N',S]dizinc(II), [Zn<sub>2</sub>(C<sub>13</sub>H<sub>11</sub>N<sub>2</sub>S)<sub>2</sub>(C<sub>2</sub>H<sub>3</sub>O<sub>2</sub>)<sub>2</sub>] (n = 2), 5, and μ-acetato-1:2κ<sup>2</sup>O:O'-acetato-2κO-[μ-(2-{[phenyl(pyridin-2-yl)methylidene]amino}phenyl)sulfanido-1κS:2κ<sup>3</sup>N,N',S][(2-{[phenyl(pyridin-2-yl)methylidene]amino}phenyl)sulfanido-1κ<sup>3</sup>N,N',S]dizinc(II)-bis(2-aminophenyl) disulfide (2/1), [Zn<sub>2</sub>(C<sub>18</sub>H<sub>13</sub>N<sub>2</sub>S)<sub>2</sub>(C<sub>2</sub>H<sub>3</sub>O<sub>2</sub>)<sub>2</sub>]·0.5C<sub>12</sub>H<sub>12</sub>N<sub>2</sub>S<sub>2</sub> (n = 3), 6·0.5(2-APS)<sub>2</sub>, were obtained from the reaction of 2-R-(pyridin-2-yl)benzothiazoline precursors (R = H, 1; R = Me, 2; R = Ph, 3) with zinc acetate dihydrate in a 1:1 ratio. All the complexes crystallized as dinuclear species and complex 6 cocrystallized with one molecule of bis(2-aminophenyl) disulfide (2-APS)<sub>2</sub>. The anionic Schiff base ligands {L<sup>n</sup>}<sup>-</sup> displayed a κ<sup>2</sup>N,κS-tridentate coordination mode with the formation of two five-membered chelate rings. In 4, 5 and 6·0.5(2-APS)<sub>2</sub>, both Zn<sup>II</sup> ions are pentacoordinated and the coordination sphere of 4 was different with respect to those in 5 and 6·0.5(2-APS)<sub>2</sub>. For 4, the X-ray diffraction study showed a dinuclear complex containing two bridging acetate ligands linked to both Zn<sup>II</sup> ions. For 5 and 6·0.5(2-APS)<sub>2</sub>, the dinuclear complexes displayed one bridging acetate ligand linked to both Zn<sup>II</sup> ions, where the first Zn<sup>II</sup> ion includes a dative bond with one S atom from an adjacent anionic Schiff base {L<sup>n</sup>}<sup>-</sup>, while the second Zn<sup>II</sup> ion is coordinated to one terminal acetate ligand. In each dinuclear complex, the geometry is the same for both Zn<sup>II</sup> metal centres. The local geometry of the Zn<sup>II</sup> cation in 4 is halfway between trigonal bipyramidal and square pyramidal local geometries; in 5 and 6, the local geometries are described as distorted square pyramidal. Hirshfeld surface analysis of 5 and 6 showed the predominance of H...H interactions, as well as the contribution of C-H...C, C-H...O and C-H...S noncovalent interactions to the cohesion of the crystalline network of the Zn<sup>II</sup> complexes.</p>","PeriodicalId":7115,"journal":{"name":"Acta Crystallographica Section C Structural Chemistry","volume":null,"pages":null},"PeriodicalIF":0.7,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142370716","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis, crystal structures and antiproliferative activities of a new indole-containing dipyridylmethanone hydrazone Schiff base and its cadmium(II) complex. 一种新的含吲哚的二吡啶基甲酮腙席夫碱及其镉(II)配合物的合成、晶体结构和抗增殖活性。
IF 0.7 4区 化学 Q4 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-01 Epub Date: 2024-10-28 DOI: 10.1107/S2053229624010167
Qing Zhang, Zi Quan Wang, Dian Xiang Xing, Shou Juan Wang, Xue Jie Tan

In this study, we introduce a novel indole-containing pyridine-based Schiff base, (E)-2-({[bis(pyridin-2-yl)methylidene]hydrazin-1-ylidene}methyl)-1H-indole, C20H15N5 (2-DPHI), and its cadmium(II) complex poly[[2-({[bis(pyridin-2-yl)methylidene]hydrazin-1-ylidene}methyl)-1H-indole]di-μ-chlorido-cadmium(II)], [CdCl2(C20H15N5)]n (pCd2), as potential anticancer agents. The Schiff base was synthesized by reacting dipyridylmethanone hydrazone with indole-2-formaldehyde, while the cadmium complex was prepared by combining CdCl2 and 2-DPHI in methanol at room temperature. Both compounds were evaluated for their cytotoxicity against three human cancer cell lines (A375, A549 and HeLa) and a normal cell line (HFF-1). The ligand 2-DPHI exhibited notable antitumour activity, with an IC50 value of 12.22 µM against A375 and 15.17 µM against A549 after 48 h, while the pCd2 complex showed an even stronger inhibition of A375 cells, with an IC50 value of 4.88 µM, outperforming both 2-DPHI and CdCl2. Both compounds demonstrated lower toxicity towards normal cells compared to cancer cells. The structures of 2-DPHI and pCd2 were fully characterized using single-crystal X-ray diffraction, elemental analysis, high-resolution mass spectrometry and FT-IR, 1H NMR, 13C NMR and UV-Vis spectroscopy.

在本研究中,我们介绍了一种新型含吲哚的吡啶基席夫碱--(E)-2-({[双(吡啶-2-基)亚甲基]肼-1-亚基}甲基)-1H-吲哚,C20H15N5 (2-DPHI)、及其镉(II)配合物聚[[2-({[双(吡啶-2-基)亚甲基]肼-1-亚基}甲基)-1H-吲哚]二-μ-氯镉(II)],[CdCl2(C20H15N5)]n(pCd2),作为潜在的抗癌剂。希夫碱是通过二吡啶基甲酮腙与吲哚-2-甲醛反应合成的,而镉配合物则是在室温下将 CdCl2 和 2-DPHI 加入甲醇中制备的。研究人员评估了这两种化合物对三种人癌细胞株(A375、A549 和 HeLa)和一种正常细胞株(HFF-1)的细胞毒性。配体 2-DPHI 显示出显著的抗肿瘤活性,48 小时后对 A375 的 IC50 值为 12.22 µM,对 A549 的 IC50 值为 15.17 µM,而 pCd2 复合物对 A375 细胞的抑制作用更强,IC50 值为 4.88 µM,优于 2-DPHI 和 CdCl2。与癌细胞相比,这两种化合物对正常细胞的毒性更低。利用单晶 X 射线衍射、元素分析、高分辨率质谱以及傅立叶变换红外光谱、1H NMR、13C NMR 和紫外可见光谱对 2-DPHI 和 pCd2 的结构进行了全面鉴定。
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引用次数: 0
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Acta Crystallographica Section C Structural Chemistry
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