C—H...O and C—H...N interactions in three hexahydrocycloocta[b]pyridine-3-carbonitriles

2014 ◽  
Vol 70 (2) ◽  
pp. 236-240
Author(s):  
R. Vishnupriya ◽  
J. Suresh ◽  
S. Maharani ◽  
R. Ranjith Kumar
Keyword(s):  
Intermolecular Interaction ◽  
Pyridine Ring ◽  
Phenyl Group ◽  
Structure Type ◽  
Interaction Patterns ◽  
Ethoxy Group ◽  
Molecular Scaffold ◽  
One Dimensional ◽  
Dimensional Network ◽  
Simple Change

The structures of three new pyridine derivatives, 2-methoxy-4-(4-methoxyphenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile, C20H22N2O2, (I), 2-ethoxy-4-(3-nitrophenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile, C20H21N3O3, (II), and 2-ethoxy-4-(4-methoxyphenyl)-5,6,7,8,9,10-hexahydrocycloocta[b]pyridine-3-carbonitrile, C21H24N2O2, (III), differ in the nature of the substituents either at the 2-position of the central pyridine ring or on the pendent aryl ring. This simple change in the structure substantially alters the intermolecular interaction patterns. The substituted phenyl group adopts a synclinal geometry with respect to the plane of the pyridine ring in all three compounds. In (I), a C—H...N interaction results in a one-dimensional chain parallel to thebaxis. In (II), there are two C—H...N(nitrile) interactions from different symmetry-related molecules, resulting in a two-dimensional network parallel to thebcplane. There is also a weak C—H...O interaction from the ethoxy group to an adjacent nitro O atom. The present work is an example of how the simple replacement of a substituent in the main molecular scaffold may transform the structure type, paving the way for a variety of supramolecular motifs and consequently altering the complexity of the intermolecular interaction patterns.

Supramolecular networks in (9-fluoro-4H-chromeno[4,3-c]isoxazol-3-yl)methanol and its 9-chloro analogue at 100 K

2012 ◽  
Vol 68 (8) ◽  
pp. o288-o293 ◽  
Author(s):  
P. Rajalakshmi ◽  
N. Srinivasan ◽  
R. V. Krishnakumar ◽  
Ibrahim Abdul Razak ◽  
Mohd Mustaqim Rosli
Keyword(s):  
Intermolecular Interaction ◽  
Point Group ◽  
Group Symmetry ◽  
Interaction Patterns ◽  
Point Group Symmetry ◽  
Orthorhombic Space Group ◽  
Molecular Scaffold ◽  
Triclinic Space Group ◽  
Space Group ◽  
Supramolecular Networks

The title compounds, (9-fluoro-4H-chromeno[4,3-c]isoxazol-3-yl)methanol, C11H8FNO3, (I), and (9-chloro-4H-chromeno[4,3-c]isoxazol-3-yl)methanol, C11H8ClNO3, (II), crystallize in the orthorhombic space groupPbcawithZ′ = 1 and the triclinic space groupP\overline{1} withZ′ = 6, respectively. The simple replacement of F by Cl in the main molecular scaffold of (I) and (II) results in significant differences in the intermolecular interaction patterns and a corresponding change in the point-group symmetry fromD2htoCi=S2. These striking differences are manifested through the presence of C—H...F and the absence of O—H...O and C—H...O interactions in (I), and the absence of C—H...Cl and the presence of O—H...O and C—H...O interactions in (II). However, the geometry of the synthons formed by the O—H...N and O—H...X(X= F or Cl) interactions observed in the constitution of the supramolecular networks of both (I) and (II) remains similar. Also, C—H...O interactions are not preferred in the presence of F in (I), while they are much preferred in the presence of Cl in (II).

Supramolecular sheets in (4H-chromeno[4,3-c]isoxazol-3-yl)methanol and its hydrated 8-methyl-substituted analogue at 100 K

2012 ◽  
Vol 68 (11) ◽  
pp. o481-o484
Author(s):  
P. Rajalakshmi ◽  
N. Srinivasan ◽  
R. V. Krishnakumar ◽  
Ibrahim Abdul Razak ◽  
Mohd Mustaqim Rosli
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Intermolecular Interaction ◽  
Hydroxy Group ◽  
Structure Type ◽  
Group Symmetry ◽  
Interaction Patterns ◽  
Supramolecular Motifs ◽  
Hydrogen Bonding Interactions

The title compounds, (4H-chromeno[4,3-c]isoxazol-3-yl)methanol, C11H9NO3, (I), and (8-methyl-4H-chromeno[4,3-c]isoxazol-3-yl)methanol monohydrate, C12H11NO3·H2O, (II), crystallize in the monoclinic space groupsP21/candC2/c, respectively. The simple addition of a methyl substituent in (II) results in a change in the structure type and substantially alters the intermolecular interaction patterns, while retaining the point-group symmetry 2/m. Compound (II) crystallizes as a hydrate and the resulting hydrogen-bonding interactions involving the water molecule are the cause of differences in the hydrogen-bonded supramolecular motifs present in (I) and (II). The water molecule in (II) is disordered over two positions having very similar orientations, with occupancies of 0.571 (18) and 0.429 (18), although the pattern of hydrogen-bonding interactions for the two disordered water molecules remains essentially the same. In both compounds, the primary donor hydroxy group adopts atransconformation with respect to the isoxazole O atom, with a torsion angle of 170.65 (8)° for (I) and 179.56 (10)° for (II), the small difference being due to differences in the hydrogen-bonding environment of the hydroxy group. In (I), molecules are linked through two independent O—H...N and C—H...O hydrogen bonds and form sheets of centrosymmetricR44(18) andR44(14) rings extending parallel to the (100) plane. The supramolecular motifs in (II) generate two-dimensional sheets parallel to the (100) plane through a combination of O—H...X(X= N, O) and C—H...O hydrogen bonds, leading to water-assisted noncentrosymmetricR22(8) andR66(20) motifs. The present work is an example of how the simple replacement of a substituent in the main molecular scaffold may transform the structure type, paving the way for a variety of supramolecular motifs and consequently altering the complexity of the intermolecular interaction patterns.

Poly[[μ2-1,3-bis(pyridin-4-yl)propane](μ3-1,4-phenylenediacetato)cadmium]

2012 ◽  
Vol 68 (2) ◽  
pp. m34-m36 ◽  
Author(s):  
Dong Liu
Keyword(s):  
Title Complex ◽  
Point Of View ◽  
Solvothermal Reaction ◽  
Dimensional Chain ◽  
Two Dimensional ◽  
One Dimensional ◽  
Connected Network ◽  
Dimensional Network

Solvothermal reaction between Cd(NO3)2, 1,4-phenylenediacetate (1,4-PDA) and 1,3-bis(pyridin-4-yl)propane (bpp) afforded the title complex, [Cd(C10H8O4)(C13H14N2)]n. Adjacent carboxylate-bridged CdIIions are related by an inversion centre. The 1,4-PDA ligands adopt acisconformation and connect the CdIIions to form a one-dimensional chain extending along thecaxis. These chains are in turn linked into a two-dimensional network through bpp bridges. The bpp ligands adopt ananti–gaucheconformation. From a topological point of view, each bpp ligand and each pair of 1,4-PDA ligands can be considered as linkers, while the dinuclear CdIIunit can be regarded as a 6-connecting node. Thus, the structure can be simplified to a two-dimensional 6-connected network.

Structural study of six cycloalkylammonium cinnamate salt structures featuring one-dimensional columns and two-dimensional hydrogen-bonded networks

2012 ◽  
Vol 68 (5) ◽  
pp. o188-o194 ◽  
Author(s):  
Andreas Lemmerer ◽  
Manuel A. Fernandes
Keyword(s):  
Hydrogen Bonds ◽  
Structural Study ◽  
Two Dimensional ◽  
One Dimensional ◽  
Dimensional Network ◽  
Polymorphic Forms ◽  
Whole Molecule Disorder ◽  
Hydrogen Bonded

Six ammonium carboxylate salts, namely cyclopentylammonium cinnamate, C5H12N+·C9H7O2−, (I), cyclohexylammonium cinnamate, C6H14N+·C9H7O2−, (II), cycloheptylammonium cinnamate form I, C7H16N+·C9H7O2−, (IIIa), and form II, (IIIb), cyclooctylammonium cinnamate, C8H18N+·C9H7O2−, (IV), and cyclododecylammonium cinnamate, C12H26N+·C9H7O2−, (V), are reported. Salts (II)–(V) all have a 1:1 ratio of cation to anion and feature three N+—H...O−hydrogen bonds forming one-dimensional hydrogen-bonded columns consisting of repeatingR43(10) rings, while salt (I) has a two-dimensional network made up of alternatingR44(12) andR68(20) rings. Salt (III) consists of two polymorphic forms,viz.form I havingZ′ = 1 and form II withZ′ = 2. The latter polymorph has disorder of the cycloheptane rings in the two cations, as well as whole-molecule disorder of one of the cinnamate anions. A similar, but ordered,Z′ = 2 structure is seen in salt (IV).

scholarly journals Crystal structures of 2-methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate and bis-[4-methylpyridinium hydrogen 2,3-bis(4-methylbenzoyloxy)succinate] pentahydrate

2017 ◽  
Vol 73 (10) ◽  
pp. 1483-1487
Author(s):  
P. Sivakumar ◽  
S. Israel ◽  
G. Chakkaravarthi
Keyword(s):  
Hydrogen Bonds ◽  
Pyridine Ring ◽  
Crystal Packing ◽  
Water Molecules ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Aromatic Rings ◽  
Π Interactions ◽  
Dimensional Network ◽  
Anions And Cations

The title salt (I), C6H8N+·C20H17O8−, comprises a 2-methylpyridinium cation and a 2,3-bis(4-methylbenzoyloxy)succinate mono-anion while the salt (II), 2C6H8N+·2C20H17O8−·5H2O, consists of a pair of 4-methylpyridinium cations and 2,3-bis(4-methylbenzoyloxy)succinate mono-anions and five water molecules of solvation in the asymmetric unit. In (I), the dihedral angle between the aromatic rings of the anion is 40.41 (15)°, comparing with 43.0 (3) and 85.7 (2)° in the conformationally dissimilar anion molecules in (II). The pyridine ring of the cation in (I) is inclined at 23.64 (16) and 42.69 (17)° to the two benzene moieties of the anion. In (II), these comparative values are 4.7 (3), 43.5 (3)° and 43.5 (3), 73.1 (3)° for the two associated cation and anion pairs. The crystal packing of (I) is stabilized by inter-ionic N—H...O, O—H...O and C—H...O hydrogen bonds as well as weak C—H...π interactions, linking the ions into infinite chains along [100]. In the crystal packing of (II), the anions and cations are also linked by N—H...O and O—H...O hydrogen bonds involving also the water molecules, giving a two-dimensional network across (001). The crystal structure is also stabilized by weak C—H...O and C—H...π interactions.

scholarly journals SOLVENT-FREE SYNTHESIS AND CRYSTAL STRUCTURE OF rac-2-THIOHYDANTOIN-VALINE

2019 ◽  
Vol 16 (31) ◽  
pp. 347-352
Author(s):  
G. E. DELGADO ◽  
Asiloé J. MORA ◽  
T. GONZÁLEZ ◽  
I. SANTOS ◽  
P. RIVAS ◽  
...  
Keyword(s):  
Heterocyclic Ring ◽  
Solvent Free ◽  
Monoclinic Space Group ◽  
X Ray Diffraction ◽  
Synthesis And Crystal Structure ◽  
One Dimensional ◽  
X Ray ◽  
Dimensional Network ◽  
Nmr Techniques ◽  
Solvent Free Synthesis

Thiohydantoins have been used in the manufacture of medicines and in industrial processes. Depending on the nature and type of substitution on the heterocyclic ring, these compounds may display pharmaceutical and biological activity with a variety of applications as antiepileptic, antitumoral, antiinflammatory, and principally for the treatment of prostate cancer. In this study, a new thiohydantoin was synthetized from the valine amino acid and structurally characterized. The title compound, C6H10N2O2S, with systematic name rac-5-isopropyl-2-tioxoimidazolidin-4-one, has been synthetized by a solvent-free synthesis. The heterocyclic compound was characterized by spectroscopic infrared (FTIR) and nuclear magnetic resonance (NMR) techniques, powder and single-crystal X-ray diffraction analysis (XRD). This material crystallizes in the monoclinic space group P21/c. In the supramolecular structure, the molecules are joined by N- --H···O and N---H···S hydrogen bonds, forming centrosymmetric R2 2(8) dimers and C2 2(9) chains that run along the [001] direction in an infinite one-dimensional network.

scholarly journals Crystal structures of 4-chloropyridine-2-carbonitrile and 6-chloropyridine-2-carbonitrile exhibit different intermolecular π-stacking, C—H...Nnitrileand C—H...Npyridineinteractions

2015 ◽  
Vol 71 (7) ◽  
pp. 852-856 ◽  
Author(s):  
Matthew J. Montgomery ◽  
Thomas J. O'Connor ◽  
Joseph M. Tanski
Keyword(s):  
Solid State ◽  
Crystal Structures ◽  
Pyridine Ring ◽  
Nitrile Group ◽  
Two Dimensional ◽  
One Dimensional ◽  
Face To Face ◽  
Π Stacking

The two title compounds are isomers of C6H3ClN2containing a pyridine ring, a nitrile group, and a chloro substituent. The molecules of each compound pack together in the solid state with offset face-to-face π-stacking, and intermolecular C—H...Nnitrileand C—H...Npyridineinteractions. 4-Chloropyridine-2-carbonitrile, (I), exhibits pairwise centrosymmetric head-to-head C—H...Nnitrileand C—H...Npyridineinteractions, forming one-dimensional chains, which are π-stacked in an offset face-to-face fashion. The intermolecular packing of the isomeric 6-chloropyridine-2-carbonitrile, (II), which differs only in the position of the chloro substituent on the pyridine ring, exhibits head-to-tail C—H...Nnitrileand C—H...Npyridineinteractions, forming two-dimensional sheets which are π-stacked in an offset face-to-face fashion. In contrast to (I), the offset face-to-face π-stacking in (II) is formed between molecules with alternating orientations of the chloro and nitrile substituents.

scholarly journals A new lanthanum(III) complex containing acetylacetone and 1H-imidazole

2017 ◽  
Vol 73 (11) ◽  
pp. 1739-1742 ◽  
Author(s):  
Atsuya Koizumi ◽  
Takuya Hasegawa ◽  
Atsushi Itadani ◽  
Kenji Toda ◽  
Taoyun Zhu ◽  
...  
Keyword(s):  
Bidentate Ligand ◽  
Bidentate Ligands ◽  
Monodentate Ligand ◽  
Intermolecular Hydrogen Bonds ◽  
Molecular Plane ◽  
One Dimensional ◽  
Nitrate N ◽  
Dimensional Network ◽  
Monodentate Ligands ◽  
Nitrate Anions

In the title complex, diaqua(1H-imidazole-κN3)(nitrato-κ2O,O′)bis(4-oxopent-2-en-2-olato-κ2O,O′)lanthanum(III), [La(C5H7O2)2(NO3)(C3H4N2)(H2O)2], the La atom is coordinated by eight O atoms of two acetylacetonate (acac) anions acting as bidentate ligands, two water molecule as monodentate ligands, one nitrate anions as a bidentate ligand and one N atom of an imidazolate (ImH) molecule as a monodentate ligand. Thus, the coordination number of the La atom is nine in a monocapped square antiprismatic polyhedron. There are three types of intermolecular hydrogen bonds between ligands, the first involving nitrate–water O...H—O interactions running along the [001] direction, the second involving acac–water O...H—O interactions along the [010] direction and the third involving an Im–nitrate N—H...O interaction along the [100] direction (five interactions of this type). Thus, an overall one-dimensional network structure is generated. The molecular plane of an ImH molecule is almost parallel to that of a nitrate ligand, making an angle of only 6.04 (12)°. Interestingly, the ImH plane is nearly perpendicular to the planes of two neighbouring acac ligands.

One-dimensional CuIIcoordination polymers containingC2h-symmetric 1,1′:4′,1′′-terphenyl-3,3′-dicarboxylate linkers

2015 ◽  
Vol 71 (10) ◽  
pp. 929-935 ◽  
Author(s):  
Hyun-Chul Kim ◽  
Ja-Min Gu ◽  
Seong Huh ◽  
Chul-Hyun Yo ◽  
Youngmee Kim
Keyword(s):  
Coordination Polymers ◽  
Three Dimensional ◽  
Polymer Chains ◽  
Water Molecules ◽  
Binding Modes ◽  
Bridging Ligands ◽  
One Dimensional ◽  
X Ray Crystallography ◽  
Dimensional Network ◽  
The One

Two new one-dimensional CuIIcoordination polymers (CPs) containing theC2h-symmetric terphenyl-based dicarboxylate linker 1,1′:4′,1′′-terphenyl-3,3′-dicarboxylate (3,3′-TPDC), namelycatena-poly[[bis(dimethylamine-κN)copper(II)]-μ-1,1′:4′,1′′-terphenyl-3,3′-dicarboxylato-κ4O,O′:O′′:O′′′] monohydrate], {[Cu(C20H12O4)(C2H7N)2]·H2O}n, (I), andcatena-poly[[aquabis(dimethylamine-κN)copper(II)]-μ-1,1′:4′,1′′-terphenyl-3,3′-dicarboxylato-κ2O3:O3′] monohydrate], {[Cu(C20H12O4)(C2H7N)2(H2O)]·H2O}n, (II), were both obtained from two different methods of preparation: one reaction was performed in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) as a potential pillar ligand and the other was carried out in the absence of the DABCO pillar. Both reactions afforded crystals of different colours,i.e.violet plates for (I) and blue needles for (II), both of which were analysed by X-ray crystallography. The 3,3′-TPDC bridging ligands coordinate the CuIIions in asymmetric chelating modes in (I) and in monodenate binding modes in (II), forming one-dimensional chains in each case. Both coordination polymers contain two coordinated dimethylamine ligands in mutuallytranspositions, and there is an additional aqua ligand in (II). The solvent water molecules are involved in hydrogen bonds between the one-dimensional coordination polymer chains, forming a two-dimensional network in (I) and a three-dimensional network in (II).

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