scholarly journals Phenol Derivatives as Co-Crystallized Templates to Modulate Trimesic-Acid-Based Hydrogen-Bonded Organic Molecular Frameworks

Crystals ◽  
2021 ◽  
Vol 11 (4) ◽  
pp. 409
Author(s):  
Guangchuan Ou ◽  
Qiong Wang ◽  
Qiang Zhou ◽  
Xiaofeng Wang
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Chain Structure ◽  
Dimensional Structure ◽  
Spectroscopy Analysis ◽  
Phenol Derivatives ◽  
Trimesic Acid ◽  
Cyclic Network ◽  
Framework Compounds ◽  
Hydrogen Bonded

Five host−guest trimesic-acid-based hydrogen-bonds framework compounds with different guests, namely [(TMA)4·(TMB)3] (1), [(TMA)2·(DMB)1.5] (2), [(TMA)6·(MP)] (3), [(TMA)·(EP)] (4) and [(TMA)·(PP)] (5) (TMA = trimesic acid, TMB = 1,3,5-trimethoxybenzene, DMB = 1,4-dimethoxybenzene, MP = 4-methoxyphenol, EP = 4-ethoxyphenol and PP = 4-propoxyphenol), were obtained through co-crystallization, and were characterized by elemental analysis, infrared spectroscopy analysis, and thermogravimetric analysis. The trimesic acid molecules comprise a hydrogen bonding six-membered cyclic host network that is found in a two-dimensional arrangement in compounds 1 and 2, and in a nine-fold interpenetrated three-dimensional structure in compound 3. In compounds 4 and 5, the trimesic acid and EP/PP molecules form a hydrogen-bonded six-membered cyclic network, resulting in a one-dimensional chain structure through O−H…O hydrogen bonds.

scholarly journals Crystal structure of a polymeric calcium levulinate dihydrate:catena-poly[[diaquacalcium]-bis(μ2-4-oxobutanoato)]

2015 ◽  
Vol 71 (5) ◽  
pp. 494-497
Author(s):  
Ananda S. Amarasekara ◽  
Dominique T. Sterling-Wells ◽  
Carlos Ordonez ◽  
Marie-Josiane Ohoueu ◽  
Marina S. Fonari
Keyword(s):  
Hydrogen Bonds ◽  
Rotation Axis ◽  
Three Dimensional ◽  
Axial Direction ◽  
Chain Structure ◽  
Dimensional Structure ◽  
Polymeric Chain ◽  
Water Molecules ◽  
Carboxylate Ligands ◽  
Length Range

In the title calcium levulinate complex, [Ca(C5H7O3)2(H2O)2]n, the Ca2+ion lies on a twofold rotation axis and is octacoordinated by two aqua ligands and six O atoms from four symmetry-related carboxylate ligands, giving a distorted square-antiprismatic coordination stereochemistry [Ca—O bond-length range = 2.355 (1)–2.599 (1) Å]. The levulinate ligands act both in a bidentate carboxylO,O′-chelate mode and in a bridging mode through one carboxyl O atom with an inversion-related Ca2+atom, giving a Ca...Ca separation of 4.0326 (7) Å. A coordination polymeric chain structure is generated, extending along thec-axial direction. The coordinating water molecules act as double donors and participate in intra-chain O—H...O hydrogen bonds with carboxyl O atoms, and in inter-chain O—H...O hydrogen bonds with carbonyl O atoms, thus forming an overall three-dimensional structure.

scholarly journals Hydrogen-bonded two- and three-dimensional polymeric structures in the ammonium salts of 3,5-dinitrobenzoic acid, 4-nitrobenzoic acid and 2,4-dichlorobenzoic acid

2014 ◽  
Vol 70 (3) ◽  
pp. 315-319 ◽  
Author(s):  
Graham Smith
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Ammonium Salts ◽  
Dimensional Structure ◽  
Water Molecules ◽  
Carboxylate Group ◽  
Two Dimensional ◽  
Structure Extension ◽  
Polymeric Structures ◽  
Hydrogen Bonded

The structures of ammonium 3,5-dinitrobenzoate, NH4+·C7H3N2O6−, (I), ammonium 4-nitrobenzoate dihydrate, NH4+·C7H4NO4−·2H2O, (II), and ammonium 2,4-dichlorobenzoate hemihydrate, NH4+·C7H3Cl2O2−·0.5H2O, (III), have been determined and their hydrogen-bonded structures are described. All three salts form hydrogen-bonded polymeric structures,viz.three-dimensional in (I) and two-dimensional in (II) and (III). With (I), a primary cation–anion cyclic association is formed [graph setR43(10)] through N—H...O hydrogen bonds, involving a carboxylate group with both O atoms contributing to the hydrogen bonds (denoted O,O′-carboxylate) on one side and a carboxylate group with one O atom involved in two hydrogen bonds (denoted O-carboxylate) on the other. Structure extension involves N—H...O hydrogen bonds to both carboxylate and nitro O-atom acceptors. With structure (II), the primary inter-species interactions and structure extension into layers lying parallel to (001) are through conjoined cyclic hydrogen-bonding motifs,viz.R43(10) (one cation, an O,O′-carboxylate group and two water molecules) and centrosymmetricR42(8) (two cations and two water molecules). The structure of (III) also has conjoinedR43(10) and centrosymmetricR42(8) motifs in the layered structure but these differ in that the first motif involves one cation, an O,O′-carboxylate group, an O-carboxylate group and one water molecule, and the second motif involves two cations and two O-carboxylate groups. The layers lie parallel to (100). The structures of salt hydrates (II) and (III), displaying two-dimensional layered arrays through conjoined hydrogen-bonded nets, provide further illustration of a previously indicated trend among ammonium salts of carboxylic acids, but the anhydrous three-dimensional structure of (I) is inconsistent with that trend.

Hydrogen bonding in 4-nitrobenzene-1,2-diamine and two hydrohalide salts

2014 ◽  
Vol 70 (7) ◽  
pp. 681-688 ◽  
Author(s):  
David K. Geiger ◽  
Dylan E. Parsons
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Nitro Group ◽  
Three Dimensional ◽  
Dimensional Structure ◽  
Planar Geometry ◽  
Amine Group ◽  
Acta Cryst ◽  
Extended Structure ◽  
Hydrogen Bonded

The structures of 4-nitrobenzene-1,2-diamine [C6H7N3O2, (I)], 2-amino-5-nitroanilinium chloride [C6H8N3O2+·Cl−, (II)] and 2-amino-5-nitroanilinium bromide monohydrate [C6H8N3O2+·Br−·H2O, (III)] are reported and their hydrogen-bonded structures described. The amine groupparato the nitro group in (I) adopts an approximately planar geometry, whereas themetaamine group is decidedly pyramidal. In the hydrogen halide salts (II) and (III), the amine groupmetato the nitro group is protonated. Compound (I) displays a pleated-sheet hydrogen-bonded two-dimensional structure withR22(14) andR44(20) rings. The sheets are joined by additional hydrogen bonds, resulting in a three-dimensional extended structure. Hydrohalide salt (II) has two formula units in the asymmetric unit that are related by a pseudo-inversion center. The dominant hydrogen-bonding interactions involve the chloride ion and result inR42(8) rings linked to form a ladder-chain structure. The chains are joined by N—H...Cl and N—H...O hydrogen bonds to form sheets parallel to (010). In hydrated hydrohalide salt (III), bromide ions are hydrogen bonded to amine and ammonium groups to formR42(8) rings. The water behaves as a double donor/single acceptor and, along with the bromide anions, forms hydrogen bonds involving the nitro, amine, and ammonium groups. The result is sheets parallel to (001) composed of alternatingR55(15) andR64(24) rings. Ammonium N—H...Br interactions join the sheets to form a three-dimensional extended structure. Energy-minimized structures obtained using DFT and MP2 calculations are consistent with the solid-state structures. Consistent with (II) and (III), calculations show that protonation of the amine groupmetato the nitro group results in a structure that is about 1.5 kJ mol−1more stable than that obtained by protonation of thepara-amine group. DFT calculations on single molecules and hydrogen-bonded pairs of molecules based on structural results obtained for (I) and for 3-nitrobenzene-1,2-diamine, (IV) [Betz & Gerber (2011).Acta Cryst.E67, o1359] were used to estimate the strength of the N—H...O(nitro) interactions for three observed motifs. The hydrogen-bonding interaction between the pairs of molecules examined was found to correspond to 20–30 kJ mol−1.

Polynuclear Co(II) and Cu(II) complexes of tetraacetylethane: CuII2(dpa)2(tae)(O2CCF3)2, {[CuII2(dpa)2(tae)(4,4'-bipy)](O2CCF3)2}n, and [CoII2(dpa)4(tae)](O2CCH3)2(H2O)2, dpa = 2,2'-dipyridylamine, tae = tetraacetylethane dianion

1999 ◽  
Vol 77 (8) ◽  
pp. 1424-1435 ◽  
Author(s):  
Yousheng Zhang ◽  
Steven R Breeze ◽  
Suning Wang ◽  
John E Greedan ◽  
N P Raju ◽  
...  
Keyword(s):  
Solid State ◽  
Molecular Sieve ◽  
Three Dimensional ◽  
Chain Structure ◽  
Dinuclear Complex ◽  
Dimensional Structure ◽  
Polymeric Compound ◽  
Bridging Ligand ◽  
Ferromagnetic Exchange ◽  
Hydrogen Bonded

The syntheses and structures of copper(II) and cobalt(II) complexes employing tetraacetylethane as the bridging ligand have been investigated. The reaction of Cu(O2CCF3)2 with tetraacetylethane (tae) and 2,2'-dipyridylamine (dpa) yielded a dinuclear complex CuII2(dpa)2(tae)(O2CCF3)2 (1), which has an extended hydrogen-bonded chain structure in the solid state. The reaction of 4,4'-dipyridyl (4,4'-bipy) with compound 1 resulted in the formation of a polymeric compound {[CuII2(dpa)2(tae)(4,4'-bipy)](O2CCF3)2}n (2), where the dinuclear unit is cross-linked by the 4,4'-dipyridyl ligand. The reaction of Co(O2CCH3)2 with tetraacetylethane and 2,2'-dipyridylamine yielded a helical dinuclear complex [CoII2(dpa)4(tae)](O2CCH3)2(H2O)2 (3), which forms a hydrogen-bonded band architecture in the solid state. The three-dimensional structure of 3 has molecular sieve-like channels that host methanol molecules reversibly. While only either negligible or weak magnetic exchanges appear to be present in compounds 1 and 2, there appears to be a significant ferromagnetic exchange in 3, which is likely caused by orbital orthogonality of the Co(II) ions, as supported by the crystal structure and EHMO calculations.Key words: cobalt, copper, polynuclear, tetraacetylethane complex, magnetism.

scholarly journals Crystal structure of a host–guest complex of the tris-urea receptor, 3-(4-nitrophenyl)-1,1-bis{2-[3-(4-nitrophenyl)ureido]ethyl}urea, that encapsulates hydrogen-bonded chains of dihydrogen phosphate anions with separate tetra-n-butylammonium counter-ions

2019 ◽  
Vol 75 (3) ◽  
pp. 319-323
Author(s):  
Ruyu Wang ◽  
Xi Shu ◽  
Yu Fan ◽  
Shoujian Li ◽  
Yongdong Jin ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Dimensional Structure ◽  
Dihydrogen Phosphate ◽  
Phosphate Anion ◽  
Compound C ◽  
Counter Ions ◽  
A Chain ◽  
Intramolecular Hydrogen ◽  
Hydrogen Bonded

The title compound, C25H25N9O9·C16H36N+·H2PO4 − (I) or (C25H25N9O9)·(n-Bu4N+)·(H2PO4 −) (systematic name: 3-(4-nitrophenyl)-1,1-bis{2-[3-(4-nitrophenyl)ureido]ethyl}urea tetrabutylammonium dihydrogen phosphate), comprises a tris-urea receptor (R), a dihydrogen phosphate anion and a tetra-n-butylammonium cation. It crystallizes with two independent formula units in the asymmetric unit. The conformations of the two tris-urea receptors are stabilized by N—H...O and C—H...O intramolecular hydrogen bonds. Each dihydrogen phosphate anion has two O—H...O intermolecular hydrogen-bonding interactions with the other dihydrogen phosphate anion. Inversion-related di-anion units are linked by further O—H...O hydrogen bonds, forming a chain propagating along the a-axis direction. Each dihydrogen phosphate anion makes a total of four N—H...O(H2PO4 −) hydrogen bonds with two ureido subunits from two different tris-urea receptors, hence each tris-urea receptor provides the two ureido subunits for the encapsulation of the H2PO4 − hydrogen-bonded chain. There are numerous intermolecular C—H...O hydrogen bonds present involving both receptor molecules and the tetra-n-butylammonium cations, so forming a supramolecular three-dimensional structure. One of the butyl groups and one of the nitro groups are disordered over two positions of equal occupancy.

A supramolecular ladder-like network from trimesic acid and pyrazineN,N′-dioxide

2013 ◽  
Vol 70 (1) ◽  
pp. 43-45
Author(s):  
Vitthal N. Yadav ◽  
Carl Henrik Görbitz
Keyword(s):  
Hydrogen Bonds ◽  
Intermolecular Interactions ◽  
Three Dimensional ◽  
Tricarboxylic Acid ◽  
Title Complex ◽  
Two Dimensional ◽  
Trimesic Acid ◽  
Dimensional Network ◽  
Hydrogen Bonded

In the title complex, benzene-1,3,5-tricarboxylic acid–pyrazineN,N′-dioxide (2/1), C9H6O6·0.5C4H4N2O2, cocrystallized trimesic acid (TMA) and pyrazineN,N′-dioxide (PNO) molecules form strong O—H...O hydrogen bonds, but also important weak C—H...O and dipole–dipole intermolecular interactions, to generate a densely packed three-dimensional network. PNO molecules lie on inversion centres where they connect pairs of TMA sheets into distinct two-dimensional hydrogen-bonded layers perpendicular to the crystallographicabdiagonal.

Three-dimensional hydrogen-bonded assembly in 2,2′-disulfanylidene-5,5′-biimidazolidinylidene-4,4′-dione–dimethylformamide–water (3/2/4)

2013 ◽  
Vol 69 (12) ◽  
pp. 1545-1548 ◽  
Author(s):  
De-Hong Wu
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Dimensional Structure ◽  
Water Molecules ◽  
Two Dimensional ◽  
Hydrogen Bonding Interactions ◽  
Graph Set ◽  
Ribbon Structures ◽  
Hydrogen Bonded

The title compound, 3C6H4N4O2S2·2C3H7NO·4H2O, comprises three 2,2′-disulfanylidene-5,5′-biimidazolidinylidene-4,4′-dione molecules, two dimethylformamide molecules and four water molecules arranged around a crystallographic inversion centre. The non-H atoms within the 5,5′-biimidazolidinylidene molecule are coplanar and these molecules aggregate through N—H...S hydrogen-bonding interactions with cyclic motifs [graph setR22(8)], giving two-dimensional ribbon structures which are close to being parallel. The two independent water molecules associate to form centrosymmetric cyclic hydrogen-bonded (H2O)4tetrameric units [graph setR44(8)]. The ribbon structures extend along theaaxis and are linked through the water tetramers and the dimethylformamide molecules by a combination of two- and three-centre hydrogen bonds, giving an overall three-dimensional structure.

scholarly journals Three-dimensional hydrogen-bonded structures in the hydrated proton-transfer salts of isonipecotamide with the dicarboxylic oxalic and adipic acid homologues

2013 ◽  
Vol 69 (10) ◽  
pp. 1192-1195
Author(s):  
Graham Smith ◽  
Urs D. Wermuth
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Adipic Acid ◽  
Three Dimensional ◽  
Dimensional Structure ◽  
Water Molecules ◽  
Solvent Water ◽  
Hydrated Proton ◽  
Hydrogen Bonded

The structures of the 1:1 hydrated proton-transfer compounds of isonipecotamide (piperidine-4-carboxamide) with oxalic acid, 4-carbamoylpiperidinium hydrogen oxalate dihydrate, C6H13N2O+·C2HO4−·2H2O, (I), and with adipic acid, bis(4-carbamoylpiperidinium) adipate dihydrate, 2C6H13N2O+·C6H8O42−·2H2O, (II), are three-dimensional hydrogen-bonded constructs involving several different types of enlarged water-bridged cyclic associations. In the structure of (I), the oxalate monoanions give head-to-tail carboxylic acid O—H...Ocarboxylhydrogen-bonding interactions, formingC(5) chain substructures which extend alonga. The isonipecotamide cations also give parallel chain substructures through amide N—H...O hydrogen bonds, the chains being linked acrossband downcby alternating water bridges involving both carboxyl and amide O-atom acceptors and amide and piperidinium N—H...Ocarboxylhydrogen bonds, generating cyclicR43(10) andR32(11) motifs. In the structure of (II), the asymmetric unit comprises a piperidinium cation, half an adipate dianion, which lies across a crystallographic inversion centre, and a solvent water molecule. In the crystal structure, the two inversion-related cations are interlinked through the two water molecules, which act as acceptors in dual amide N—H...Owaterhydrogen bonds, to give a cyclicR42(8) association which is conjoined with anR44(12) motif. Further N—H...Owater, water O—H...Oamideand piperidinium N—H...Ocarboxylhydrogen bonds give the overall three-dimensional structure. The structures reported here further demonstrate the utility of the isonipecotamide cation as a synthon for the generation of stable hydrogen-bonded structures. The presence of solvent water molecules in these structures is largely responsible for the non-occurrence of the common hydrogen-bonded amide–amide dimer, promoting instead various expanded cyclic hydrogen-bonding motifs.

The 1:1 adduct of triphenylsilanol and 4,4′-bipyridyl, and three pairwise-concomitant triclinic polymorphs of the 4:1 adduct having Z′ = 0.5, 1 and 4

2003 ◽  
Vol 59 (2) ◽  
pp. 277-286 ◽  
Author(s):  
Katharine F. Bowes ◽  
George Ferguson ◽  
Alan J. Lough ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Methanol Solution ◽  
Dimensional Structure ◽  
Triclinic Space Group ◽  
Space Group ◽  
Three Dimensional Structure ◽  
Phenyl Rings ◽  
Hydrogen Bonded

Crystallization from methanol solution of mixtures of triphenylsilanol and 4,4′-bipyridyl has given a 1:1 adduct (I), Ph3SiOH·C10H8N2, and three polymorphic 4:1 adducts (II)–(IV), (Ph3SiOH)4·C10H8N2. In (I), the components are linked by a single O—H...N hydrogen bond and by a number of C—H...π(arene) hydrogen bonds to form a continuous three-dimensional structure. Compounds (II)–(IV) are all triclinic, space group P\bar 1, with Z′ values of 0.5, 1 and 4, respectively. The basic hydrogen-bonded aggregate is the same in each of (II)–(IV), having a pair of silanol molecules linked to the bipyridyl via O—N...N hydrogen bonds and a further pair of silanol molecules linked to the first pair via O—H...O hydrogen bonds. In (II) there is just one such aggregate lying across a centre of inversion (Z′ = 0.5) and in (III) there are two such aggregates, both lying across centres of inversion (Z′ = 2 × 0.5 = 1). In (IV) there are six independent aggregates of this type, four of which lie across centres of inversion and two of which lie in general positions, so that Z′ = (4 × 0.5) + 2 = 4. While the components in (I) are fully ordered, each of (II)–(IV) exhibits extensive disorder involving both the bipyridyl units and the phenyl rings of the silanol components.

scholarly journals Crystal structure of fipronil

2017 ◽  
Vol 73 (10) ◽  
pp. 1472-1474 ◽  
Author(s):  
Hyunjin Park ◽  
Jineun Kim ◽  
Eunjin Kwon ◽  
Tae Ho Kim
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Chain Structure ◽  
Dimensional Structure ◽  
Π Interactions ◽  
Compound C ◽  
Benzene Rings ◽  
Ring Centroid

The title compound, C12H4Cl2F6N4OS {systematic name: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethane)sulfinyl]-1H-pyrazole-3-carbonitrile}, is a member of the phenylpyrazole group of acaricides, and one of the phenylpyrazole group of insecticides. The dihedral angle between the planes of the pyrazole and benzene rings is 89.03 (9)°. The fluorine atoms of the trifluoromethyl substituent on the benzene ring are disordered over two sets of sites, with occupancy ratios 0.620 (15):0.380 (15). In the crystal, C—N...π interactions [N...ring centroid = 3.607 (4) Å] together with N—H...N and C—H...F hydrogen bonds form a looped chain structure along [10\overline{1}]. Finally, N—H...O hydrogen bonds and C—Cl...π interactions [Cl...ring centroid = 3.5159 (16) Å] generate a three-dimensional structure. Additionally, there are a short intermolecular F... F contacts present.

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