Systematic Structural Modification of a Pentacyclic Helical Tubuland Host Diol

1997 ◽  
Vol 50 (11) ◽  
pp. 1053 ◽  
Author(s):  
Paul D. Ahn, ◽  
Roger Bishop, ◽  
Donald C. Craig ◽  
Gary A. Downing ◽  
Marcia L. Scudder
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Hydroxy Group ◽  
Network Structure ◽  
Crystal Engineering ◽  
Structural Modification ◽  
Dispersion Forces ◽  
Sectional Area ◽  
Space Group

Reaction of methylmagnesium chloride and pentacyclo[7.3.0.0 2,7.0 3,11 .0 6,10 ]dodecane-8,12-dione (4) yields the C2-symmetric diol (5) (62%) and the unsymmetrical diol (6) (36%) whose crystal structures are analysed in crystal engineering terms. The former isomer is the tenth member of the helical tubuland diol family, crystallizing in space groupP 3121 as a microporous lattice containing empty parallel canals with 9· 9Å2cross-sectional area. Molecules of diol (6) hydrogen bond through (-O-H)4 cycles to form layers which stack in space group P 21/c by means of hydrocarbon dispersion forces. Diol (7), the bis(trifluoromethyl) analogue of (5), does not form a helical tubuland lattice. The structure of its hemihydrate also contains (–O–H)4 cycles but here the second diol hydroxy group hydrogen bonds to water resulting in a network structure in space group P-421c.

scholarly journals Crystal structures of 2-aminopyridine citric acid salts: C5H7N2 +·C6H7O7 − and 3C5H7N2 +·C6H5O7 3−

2018 ◽  
Vol 74 (8) ◽  
pp. 1111-1116 ◽  
Author(s):  
Shet M. Prakash ◽  
S. Naveen ◽  
N. K. Lokanath ◽  
P. A. Suchetan ◽  
Ismail Warad
Keyword(s):  
Hydrogen Bond ◽  
Citric Acid ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Crystal Engineering ◽  
Molecular Conformation ◽  
Crystal Packing ◽  
Three Dimensional ◽  
Dimensional Structure ◽  
Almost All

2-Aminopyridine and citric acid mixed in 1:1 and 3:1 ratios in ethanol yielded crystals of two 2-aminopyridinium citrate salts, viz. C5H7N2 +·C6H7O7 − (I) (systematic name: 2-aminopyridin-1-ium 3-carboxy-2-carboxymethyl-2-hydroxypropanoate), and 3C5H7N2 +·C6H5O7 3− (II) [systematic name: tris(2-aminopyridin-1-ium) 2-hydroxypropane-1,2,3-tricarboxylate]. The supramolecular synthons present are analysed and their effect upon the crystal packing is presented in the context of crystal engineering. Salt I is formed by the protonation of the pyridine N atom and deprotonation of the central carboxylic group of citric acid, while in II all three carboxylic groups of the acid are deprotonated and the charges are compensated for by three 2-aminopyridinium cations. In both structures, a complex supramolecular three-dimensional architecture is formed. In I, the supramolecular aggregation results from Namino—H...Oacid, Oacid...H—Oacid, Oalcohol—H...Oacid, Namino—H...Oalcohol, Npy—H...Oalcohol and Car—H...Oacid interactions. The molecular conformation of the citrate ion (CA3−) in II is stabilized by an intramolecular Oalcohol—H...Oacid hydrogen bond that encloses an S(6) ring motif. The complex three-dimensional structure of II features Namino—H...Oacid, Npy—H...Oacid and several Car—H...Oacid hydrogen bonds. In the crystal of I, the common charge-assisted 2-aminopyridinium–carboxylate heterosynthon exhibited in many 2-aminopyridinium carboxylates is not observed, instead chains of N—H...O hydrogen bonds and hetero O—H...O dimers are formed. In the crystal of II, the 2-aminopyridinium–carboxylate heterosynthon is sustained, while hetero O—H...O dimers are not observed. The crystal structures of both salts display a variety of hydrogen bonds as almost all of the hydrogen-bond donors and acceptors present are involved in hydrogen bonding.

scholarly journals Threefold helical assembly via hydroxy hydrogen bonds: the 2:1 co-crystal of bicyclo[3.3.0]octane-endo-3,endo-7-diol and bicyclo[3.3.0]octane-endo-3,exo-7-diol

2021 ◽  
Vol 77 (3) ◽  
pp. 270-276
Author(s):  
Isa Y. H. Chan ◽  
Mohan M. Bhadbhade ◽  
Roger Bishop
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Hydroxy Group ◽  
Network Structure ◽  
General Position ◽  
Three Dimensional ◽  
Screw Axis ◽  
Hydroxy Groups

Reduction of bicyclo[3.3.0]octane-3,7-dione yields a mixture of the endo-3,endo-7-diol and endo-3, exo-7-diol (C8H14O2) isomers (5 and 6). These form (5)2·(6) co-crystals in the monoclinic P21/n space group (with Z = 6, Z′ = 1.5) rather than undergoing separation by means of fractional recrystallization or column chromatography. The molecule of 5 occupies a general position, whereas the molecule of 6 is disordered over two orientations across a centre of symmetry with occupancies of 0.463 (2) and 0.037 (2). Individual diol hydroxy groups associate around a pseudo-threefold screw axis by means of hydrogen bonding. The second hydroxy group of each diol behaves in a similar manner, generating a three-dimensional hydrogen-bonded network structure. This hydrogen-bond connectivity is identical to that present in three known helical tubuland diol–hydroquinone co-crystals, and the new crystal structure is even more similar to two homologous aliphatic diol co-crystals.

scholarly journals The crystal structures of three 3-methyl-1H-1,2,4-triazole-5-thiones, including a second polymorph of 4-[(E)-(5-bromo-2-hydroxybenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione and a redetermination of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione

2015 ◽  
Vol 71 (9) ◽  
pp. 1003-1009 ◽  
Author(s):  
Padmanabha S. Manjula ◽  
Balladka K. Sarojini ◽  
Hemmige S. Yathirajan ◽  
Mehmet Akkurt ◽  
Cem Cüneyt Ersanlı ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Dihedral Angle ◽  
Compound I ◽  
Methyl Group ◽  
Space Group ◽  
Improved Model ◽  
Compound Ii

The structures of three 3-methyl-1H-1,2,4-triazole-5-thione derivatives are reported. The structure of 4-amino-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C3H6N4S, (I), has been redetermined with an improved model for the H atoms: the non-H atoms of (I) all lie on mirror planes in space groupPbcm, and the H atoms of the methyl group are disordered over two sets of reflection-related atomic sites having occupancy 0.5: two independent N—H...S hydrogen bonds link the molecules of compound (I) into complex sheets. The non-H atoms in the molecules of 4-[(E)-(3,4-dimethoxybenzylidene)amino]-3-methyl-1H-1,2,4-triazol-5(4H)-thione, C12H14N4O2S, (II), despite lying in general positions are close to planar, with a dihedral angle between the two rings of 6.31 (10)°: the molecules of compound (II) are linked by a three-centre N—H...(O)2hydrogen bond into aC(10)C(11)[R12(5)] chain of rings. A second polymorph of 4-[(E)-(5-bromo-2-hydroxy-5-bromobenzylidene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione, C10H9BrN4OS, (III), has been identified; the non-H atoms are nearly co-planar with a dihedral angle between the two rings of 1.9 (4)°. There is an intramolecular O—H...N hydrogen bond and the molecules are linked by N—H...S hydrogen bonds, forming centrosymmetricR22(8) dimers. Comparisons are made with some related structures.

scholarly journals The crystal structures of two chalcones: (2E)-1-(5-chlorothiophen-2-yl)-3-(2-methylphenyl)prop-2-en-1-one and (2E)-1-(anthracen-9-yl)-3-[4-(propan-2-yl)phenyl]prop-2-en-1-one

2016 ◽  
Vol 72 (8) ◽  
pp. 1153-1158 ◽  
Author(s):  
Marisiddaiah Girisha ◽  
Hemmige S. Yathirajan ◽  
Jerry P. Jasinski ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
The Other ◽  
Single Type ◽  
Compound I ◽  
Space Group ◽  
Compound Ii

In the crystal of compound (I), C14H11ClOS, molecules are linked by C—H...O hydrogen bonds to form simpleC(5) chains. Compound (II), C26H22O, crystallizes withZ′ = 2 in space groupP-1; one of the molecules is fully ordered but the other is disordered over two sets of atomic sites having occupancies 0.644 (3) and 0.356 (3). The two disordered components differ from one another in the orientation of the isopropyl substituents, and both differ from the ordered molecules in the arrangement of the central propenone spacer unit, so that the crystal of (II) contains three distinct conformers. The ordered and disordered conformers each form aC(8) chain built from a single type of C—H...O hydrogen bond but those formed by the disordered conformers differ from that formed by the ordered form.

scholarly journals Structural investigation of N-[2-(4-fluoro-3-phenoxybenzoyl)hydrazinecarbothioyl]benzamide and N-[2-(4-fluoro-3-phenoxybenzoyl)hydrazinecarbothioyl]-4-methoxybenzamide

2021 ◽  
Vol 77 (3) ◽  
pp. 277-281
Author(s):  
Dhananjay Dey ◽  
I. Shruti ◽  
Deepak Chopra ◽  
T. P. Mohan
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Structural Investigation ◽  
Molecular Conformation ◽  
Hirshfeld Surface ◽  
Supramolecular Network ◽  
Methoxy Derivative ◽  
Space Group ◽  
Centrosymmetric Space Group

The compound N-[2-(4-fluoro-3-phenoxybenzoyl)hydrazinecarbothioyl]benzamide, C21H16FN3O3S, crystallizes in the monoclinic centrosymmetric space group P21/c and its molecular conformation is stabilized via an intramolecular N—H...O hydrogen bond. The corresponding para-methoxy derivative, namely, N-[2-(4-fluoro-3-phenoxybenzoyl)hydrazinecarbothioyl]-4-methoxybenzamide, C22H18FN3O4S, crystallizes in the monoclinic centrosymmetric space group C2/c. The supramolecular network mainly comprises N—H...O, N—H...S and C—H...O hydrogen bonds, which contribute towards the formation of the crystal structures for the two molecules. The different intermolecular interactions have been further analysed using Hirshfeld surface analysis and fingerprint plots.

scholarly journals Crystal structures of two hydrazide derivatives of mefenamic acid, 3-(2,3-dimethylanilino)-N′-[(E)-(furan-2-yl)methylidene]benzohydrazide and N′-[(E)-benzylidene]-2-(2,3-dimethylanilino)benzohydrazide

2021 ◽  
Vol 77 (3) ◽  
pp. 242-246
Author(s):  
Shaaban K. Mohamed ◽  
Joel T. Mague ◽  
Mehmet Akkurt ◽  
Mustafa R. Albayati ◽  
Sahar M. I. Elgarhy ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Benzene Ring ◽  
Network Structure ◽  
Mefenamic Acid ◽  
Three Dimensional ◽  
Dimensional Network ◽  
Molecular And Crystal Structures ◽  
Derivatives Of

The conformation about the central benzene ring in the molecule of (I), C20H19N3O2, is partially determined by an intramolecular N—H...O hydrogen bond. In the crystal, chains parallel to the c axis are generated by intermolecular N—H...O hydrogen bonds with the chains assembled into a three-dimensional network structure by intermolecular C—H...O hydrogen bonds and C—H...π(ring) interactions. The molecule of (II), C22H21N3O, differs from (I) only in the substituent at the hydrazide N atom where a phenylmethylene moiety for (II) is present instead of a furanmethylene moiety for (I). Hence, molecules of (I) and (II) show similarities in their molecular and crystal structures. The conformation of the central portion of the molecule of (II) is also therefore partially determined by an intramolecular N—H...O hydrogen bond and intermolecular N—H...O hydrogen bonds form chains parallel to the c axis. Likewise, the chains are connected into a three-dimensional network by C—H...O hydrogen bonds and C—H...π(ring) interactions.

Polysulfonylamine, CXII. Neues aus der Festkörperchemie der 2-Pyridone: Isolierung und Röntgenstrukturen von Bis(2-pyridon)hydrogen(I)- und Bis(6-methyl-2-pyridon)hydrogen(I)-dimesylamid / Polysulfonylamines, CXII. A Novel Solid-State Aspect of 2-Pyridones: Isolation and X-Ray Structures of Bis(2-pyridone)hydrogen(I) and Bis(6-methyl-2-pyridone)hydrogen(I) Dimesylamides

1999 ◽  
Vol 54 (5) ◽  
pp. 643-648 ◽  
Author(s):  
Karna Wijaya ◽  
Oliver Moers ◽  
Armand Blaschette ◽  
Peter G. Jones
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Monoclinic Space Group ◽  
Space Group ◽  
X Ray ◽  
Crystal Packings

The compounds (2-pyridone)2H+(MeSO2)2N- (1, monoclinic, space group P21/n ) and (6- methyl-2-pyridone)2H+(MeSO2)2N- (2, triclinic, P1) crystallize selectively and in good yields when the parent 2-pyridones (2-hydroxypyridines) are treated with the strong NH acid dimesylamine in acetonitrile or acetone. The corresponding 2-hydroxypyridinium salts could not be obtained. In the unprecedented crystal structures of 1 and 2, two pyridone units are linked by a proton to form very short and approximately symmetric O⋯H+ ⋯O hydrogen bonds, the adjacent C-O distances being appreciably elongated as compared to “free” pyridones [1: O ⋯ O 241.8(2), C -O 127.8(3) and 129.1(2) pm; 2: O ⋯ O 243.8(2), C -O 128.1(2) and 129.2(2) pm]. In both crystal packings, the homoconjugate cations and the dimesylamide anions are alternately associated into chains by an N - H ⋯ N “ and an N - H ⋯ O hydrogen bond.

scholarly journals Crystal structures of (E)-1-{3-[(5-fluoro-2-hydroxybenzylidene)amino]phenyl}ethanone and of a fourth polymorph of (E)-1-{3-[(2-hydroxy-3-methoxybenzylidene)amino]phenyl}ethanone

2017 ◽  
Vol 73 (12) ◽  
pp. 1835-1839 ◽  
Author(s):  
Marisiddaiah Girisha ◽  
Hemmige S. Yathirajan ◽  
Ravindranath S. Rathore ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Space Group

In the molecules of both (E)-1-{3-[(5-fluoro-2-hydroxybenzylidene)amino]phenyl}ethanone, C15H12FNO2, (I), and (E)-1-{3-[(2-hydroxy-3-methoxybenzylidene)amino]phenyl}ethanone, C16H15NO3, (II), which crystallizes withZ′ = 2 in space groupPca21, there are intramolecular O—H...N hydrogen bonds, and the non-H atoms in each molecule are essentially coplanar. In the crystal of (I), molecules are linked by a single C—H...O hydrogen bond to form aC(8) chain, whereas in the crystal of (II), molecules are linked by three C—H...O hydrogen bonds to form sheets within which orthogonalC22(16) andC22(17) chains can be identified. Comparisons are made with some related structures.

scholarly journals Crystal-to-Crystal Transformation from K2[Co(C2O4)2(H2O)2]·4H2O to K2[Co(μ-C2O4)(C2O4)]

2021 ◽  
Vol 7 (6) ◽  
pp. 77
Author(s):  
Bin Zhang ◽  
Yan Zhang ◽  
Guangcai Chang ◽  
Zheming Wang ◽  
Daoben Zhu
Keyword(s):  
Hydrogen Bond ◽  
Physical Properties ◽  
Crystal Structures ◽  
Molecular Crystal ◽  
Trigonal Prism ◽  
Space Group ◽  
Cell Parameters ◽  
Oxalate Anion ◽  
Crystal Transformation ◽  
Antiferromagnetic Ordering

Crystal-to-crystal transformation is a path to obtain crystals with different crystal structures and physical properties. K2[Co(C2O4)2(H2O)2]·4H2O (1) is obtained from K2C2O4·2H2O, CoCl2·6H2O in H2O with a yield of 60%. It is crystallized in the triclinic with space group P1 and cell parameters: a = 7.684(1) Å, b = 9.011(1) Å, c = 10.874(1) Å, α = 72.151(2)°, β = 70.278(2)°, γ = 80.430(2)°, V = 670.0(1) Å3, Z = 2 at 100 K. 1 is composed of K+, mononuclear anion [Co(C2O4)2(H2O)22−] and H2O. Co2+ is coordinated by two bidentated oxalate anion and two H2O in an octahedron environment. There is a hydrogen bond between mononuclear anion [Co(C2O4)2(H2O)22−] and H2O. K2[Co(μ-C2O4)(C2O4)] (2) is obtained from 1 by dehydration. The cell parameters of 2 are a = 8.460(5) Å, b = 6.906 (4) Å, c = 14.657(8) Å, β = 93.11(1)°, V = 855.0(8) Å3 at 100 K, with space group in P2/c. It is composed of K+ and zigzag [Co(μ-C2O4)(C2O42−]n chain. Co2+ is coordinated by two bisbendentate oxalate and one bidentated oxalate anion in trigonal-prism. 1 is an antiferromagnetic molecular crystal. The antiferromagnetic ordering at 8.2 K is observed in 2.

Supramolecular assembling using synthons with NH—CO(S)—CS—NH and NH—CO—CO—NH functionalities: crystal structures of (S,S)-N,N′-monothiooxalyldileucine methyl ester and its dithio analogue

2004 ◽  
Vol 60 (1) ◽  
pp. 90-96 ◽  
Author(s):  
Biserka Kojić-Prodić ◽  
Berislav Perić ◽  
Zoran Štefanić ◽  
Anton Meden ◽  
Janja Makarević ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Methyl Ester ◽  
Crystal Structures ◽  
Hydrogen Bond Network ◽  
Asymmetric Unit ◽  
Orthorhombic Space Group ◽  
Space Group ◽  
Bond Network ◽  
Bonding Systems

To compare the structural properties of oxalamide and thiooxalamide groups in the formation of hydrogen bonds suitable for supramolecular assemblies a series of retropeptides was studied. Some of them, having oxalamide bridges, are gelators of organic solvents and water. However, retropeptides with oxygen replaced by the sp 2 sulfur have not exhibited such properties. The crystal structures of the two title compounds are homostructural, i.e. they have similar packing arrangements. The monothio compound crystallizes in the orthorhombic space group P212121 with two molecules in the asymmetric unit arranged in a hydrogen-bond network with an approximate 41 axis along the crystallographic b axis. However, the dithio and dioxo analogues crystallize in the tetragonal space group P41 with similar packing patterns and hydrogen-bonding systems arranged in agreement with a crystallographic 41 axis. Thus, these two analogues are isostructural having closely related hydrogen-bonding patterns in spite of the different size and polarity of oxygen and sulfur which serve as the proton acceptors.

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