scholarly journals Comparison crystal structure conformations of two structurally related biphenyl analogues: 4,4′-bis[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]-1,1′-biphenyl and 4,4′-bis{3-[(S)-2-methylpyrrolidin-1-yl]prop-1-yn-1-yl}-1,1′-biphenyl

2015 ◽  
Vol 71 (10) ◽  
pp. 1147-1150
Author(s):  
Anqi Wan ◽  
Narsimha Reddy Penthala ◽  
E. Kim Fifer ◽  
Sean Parkin ◽  
Peter A. Crooks
Keyword(s):  
Room Temperature ◽  
Lone Pair ◽  
Ring System ◽  
Asymmetric Unit ◽  
Compound I ◽  
Pyrrolidine Ring ◽  
Torsion Angles ◽  
Phenyl Rings ◽  
Nitrogen Lone Pair ◽  
Compound Ii

The title compounds, C26H28N2, (I), and C28H32N2, (II), were designed based on the structure of the potent α9α10 nicotinic acetylcholine receptor antagonist ZZ161C {1,1′-[[1,1′-biphenyl]-4,4′-diylbis(prop-2-yne-3,1-diyl)]bis(3,4-dimethylpyridin-1-ium) bromide}. In order to improve the druglikeness properties of ZZ161C for potential oral administration, the title compounds (I) and (II) were prepared by coupling 4,4′-bis(3-bromoprop-1-yn-1-yl)-1,1′-biphenyl with pyrrolidine, (I), and (S)-2-methylpyrrolidine, (II), respectively, in acetonitrile at room temperature. The asymmetric unit of (I) contains two half molecules that each sit on sites of crystallographic inversion. As a result, the biphenyl ring systems in compound (I) are coplanar. The biphenyl ring system in compound (II), however, has a dihedral angle of 28.76 (11)°. In (I), the two independent molecules differ in the orientation of the pyrrolidine ring (the nitrogen lone pair points towards the biphenyl rings in one molecule, but away from the rings in the other). The torsion angles about the ethynyl groups between the planes of the phenyl rings and the pyrrolidine ringNatoms are 84.15 (10) and −152.89 (10)°. In compound (II), the corresponding torsion angles are 122.0 (3) and 167.0 (3)°, with the nitrogen lone pairs at both ends of the molecule directed away from the central biphenyl rings.

scholarly journals Crystal structures of two new carbazole derivatives: 12-(4-nitrophenyl)-7-phenylsulfonyl-7H-benzofuro[2,3-b]carbazole and 2-methyl-4-(4-nitrophenyl)-9-phenylsulfonyl-9H-thieno[2,3-b]carbazole

2016 ◽  
Vol 72 (12) ◽  
pp. 1739-1743
Author(s):  
K. Swaminathan ◽  
P. Narayanan ◽  
K. Sethusankar ◽  
Velu Saravanan ◽  
Arasambattu K. Mohanakrishnan
Keyword(s):  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Ring System ◽  
Molecular Structures ◽  
Dihedral Angles ◽  
Compound I ◽  
Carbazole Derivatives ◽  
Phenyl Rings ◽  
The Mean ◽  
Compound Ii

The title compounds, C30H18N2O5S, (I), and C27H18N2O4S2, (II), are carbazole derivatives with a phenylsulfonyl group and a nitrophenyl group attached to the carbazole moiety in identical positions in both molecules. A benzofuran ring system in (I) and a methylthiophene ring in (II) are fused with the respective carbazole moieties on the same sides. The mean plane of the carbazole ring system makes a dihedral angle of 3.17 (7)° with the benzofuran ring system in (I) and a dihedral angle of 3.39 (11)° with the methylthiophene ring in (II), implying that both fused units are essentially planar. The mean planes of the carbazole ring systems in both the compounds are almost orthogonal to the respective nitro-substituted phenyl rings, making dihedral angles of 75.64 (10) and 77.63 (12)° in compounds (I) and (II), respectively. In (I), the phenylsulfonyl ring system is positionally disordered with a refined occupancy ratio of 0.63 (2):0.37 (2). In both compounds, the molecular structures are stabilized by intramolecular C—H...O hydrogen bonds, generatingS(6) ring motifs with the sulfone group O atoms. In the crystal of compound (I), molecules are linked by pairs of C—H...O hydrogen bonds, which generateR22(18) inversion dimers, and interconnected byC(14) chains running along thec-axis direction, whereas in compound (II), the C—H...O hydrogen bonds generateR43(37) ring motifs. In the crystals of both compounds, C—H...O hydrogen-bonded sheets are formed lying parallel to (10-1). In addition, C—H...π and offset π–π interactions [intercentroid distance = 3.7158 (14) Å in (I) and 3.9040 (15) Å in (II)] are also present in the crystals of both compounds.

scholarly journals Crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1H-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1H-indole

2017 ◽  
Vol 73 (10) ◽  
pp. 1555-1559
Author(s):  
G. Dhanalakshmi ◽  
Velu Saravanan ◽  
Arasambattu K. Mohanakrishnan ◽  
S. Aravindhan
Keyword(s):  
Hydrogen Bonds ◽  
Ring System ◽  
Dihedral Angles ◽  
Indole Derivatives ◽  
Indole Ring ◽  
Compound I ◽  
Tetrahedral Geometry ◽  
Distorted Tetrahedral Geometry ◽  
Phenyl Rings ◽  
Compound Ii

In the title indole derivatives, C22H16N2O5S, (I) and C20H15NO3S2, (II), the sulfonyl-bound phenyl rings are almost orthogonal to the indole ring system, subtending dihedral angles of 88.33 (10) and 87.58 (16)°, respectively. In both compounds, the sulfonyl S atom has a distorted tetrahedral geometry [O—S—O = 119.98 (9) and N—S—C = 104.01 (8)° for compound (I) and O—S—O = 120.08 (18) and N—S—C = 104.91 (14)° for compound (II)] and the sum of the bond angles at N indicatessp2hybridization. The molecules of both (I) and (II) feature intramolecular C—H...O hydrogen bonds that generateS(6) ring motifs with the sulfone O atom. In the crystals, molecules of (I) are linked by C—H—O hydrogen bonds, formingR44(18) ring motifs while molecules of (II) are linked by C—H—O and C—H—S hydrogen bonds, formingR22(12) ring motifs. Compound (II) was refined as an inversion twin.

scholarly journals Crystal structures of [μ2-(Ra ,Sa ,3aR,7aR)-1,3-bis(2,7-dicyclohexylnaphthalen-1-yl)octahydro-1H-benzo[d]imidazolidin-2-ylidene]chlorido(η4-1,5-cyclooctadiene)iridium dichloromethane monosolvate and [μ2-(Sa ,Sa ,3aR,7aR)-1,3-bis(2,7-dicyclohexylnaphthalen-1-yl)octahydro-1H-benzo[d]imidazolidin-2-ylidene]chlorido(η4-1,5-cyclooctadiene)iridium

2020 ◽  
Vol 76 (10) ◽  
pp. 1543-1547
Author(s):  
Stephen A. Moggach ◽  
Brian W. Skelton ◽  
Daven J. Foster
Keyword(s):  
Solvent Molecule ◽  
Iridium Complexes ◽  
Asymmetric Unit ◽  
Compound I ◽  
Monoclinic System ◽  
Torsion Angles ◽  
Bond Lengths ◽  
H Nmr ◽  
Compound Ii ◽  
Diastereomeric Complexes

The title compounds, [Ir(C51H64N2)Cl(C8H12)]·CH2Cl2, (I), and [Ir(C51H64N2)Cl(C8H12)], (II), represent the first two examples of hexahydrobenzoimidazole-based N-heterocyclic carbene (NHC) iridium complexes. The diastereomeric complexes differing only in their axial chirality, which could be separated via column chromatography, show noticeable differences in their 1H NMR spectra. Compound (I) crystallizes in the monoclinic system (P21) with two independent complexes and two half-occupied dichloromethane molecules in the asymmetric unit, while compound (II) crystallizes in the orthorhombic system (P212121) with one complex in the asymmetric unit. The fused five-membered N-heterocycles of NHCs show unusually high backbone torsion angles of −34.1 (5) and −30.9 (5)° for (I) and −31.5 (7)° for (II), but the Ir—Ccarbene bond lengths of 2.046 (6) and 2.021 (6) Å for (I) and 2.045 (8) Å for (II) present typical NHC—Ir bond lengths. The solvent molecule in the crystal of (I) was found to be highly disordered and its contribution to the scattering was masked using the solvent-masking routine smtbx.mask in OLEX2 [Dolomanov et al. (2009). J. Appl. Cryst. 42, 339–341]. The solvent contribution is not included in the reported chemical formula and other crystal data.

scholarly journals Comparison of the crystal structures of 4,4′-bis[3-(4-methylpiperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphenyl and 4,4′-bis[3-(2,2,6,6-tetramethylpiperidin-1-yl)prop-1-yn-1-yl]-1,1′-biphenyl

2015 ◽  
Vol 71 (10) ◽  
pp. 1132-1135 ◽  
Author(s):  
Anqi Wan ◽  
Narsimha Reddy Penthala ◽  
E. Kim Fifer ◽  
Sean Parkin ◽  
Peter A. Crooks
Keyword(s):  
Nicotinic Acetylcholine Receptor ◽  
Room Temperature ◽  
Interplanar Spacing ◽  
Chair Conformation ◽  
Piperidine Ring ◽  
Dihedral Angles ◽  
Compound I ◽  
Nicotinic Acetylcholine ◽  
Phenyl Rings ◽  
Compound Ii

As part of a comprehensive program to discover α9α10 nicotinic acetylcholine receptor antagonists, the title compounds C30H36N2, (I), and C36H48N2, (II), were synthesized by coupling 4,4′-bis(3-bromoprop-1-yn-1-yl)-1,1′-biphenyl with 4-methylpiperidine and 2,2,6,6-tetramethylpiperidine, respectively, in acetonitrile at room temperature. In compound (I), the biphenyl system has a twisted conformation with a dihedral angle of 26.57 (6)° between the two phenyl rings of the biphenyl moiety, while in compound (II), the biphenyl moiety sits on a crystallographic inversion centre so the two phenyl rings are exactly coplanar. The terminal piperidine rings in both compound (I) and compound (II) are in the chair conformation. In compound (I), the dihedral angles about the ethynyl groups between the planes of the phenyl rings and the piperidine ring N atoms are 37.16 (16) and 14.20 (17)°. In compound (II), the corresponding dihedral angles are both 61.48 (17)°. There are no noteworthy intermolecular interactions in (I), but in (II) there is a small π-overlap between inversion-related molecules (1 − x, 1 − y, 1 − z), with an interplanar spacing of 3.553 (3) Å and centroid-to-centroid separation of 3.859 (4) Å.

scholarly journals Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one

2019 ◽  
Vol 75 (8) ◽  
pp. 1117-1122
Author(s):  
S. Syed Abuthahir ◽  
M. NizamMohideen ◽  
S. Mayakrishnan ◽  
N. Uma Maheswari ◽  
V. Viswanathan
Keyword(s):  
Three Dimensional ◽  
Ring System ◽  
Dimensional Structure ◽  
Asymmetric Unit ◽  
Three Dimensional Structure ◽  
Π Interactions ◽  
Phenyl Rings ◽  
The Mean ◽  
Independent Molecules ◽  
Compound Ii

The title compounds, 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one, C22H17NO2, (I), and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one, C14H17NO2, (II), are new isocoumarin derivatives in which the isochromene ring systems are planar. Compound II crystallizes with two independent molecules (A and B) in the asymmetric unit. In I, the two phenyl rings are inclined to each other by 56.41 (7)° and to the mean plane of the 1H-isochromene ring system by 67.64 (6) and 44.92 (6)°. In both compounds, there is an intramolecular N—H...O hydrogen bond present forming an S(6) ring motif. In the crystal of I, molecules are linked by N—H...π interactions, forming chains along the b-axis direction. A C—H...π interaction links the chains to form layers parallel to (100). The layers are then linked by a second C—H...π interaction, forming a three-dimensional structure. In the crystal of II, the two independent molecules (A and B) are linked by N—H...O hydrogen bonds, forming –A–B–A–B– chains along the [101] direction. The chains are linked into ribbons by C—H...π interactions involving inversion-related A molecules. The latter are linked by offset π–π interactions [intercentroid distances vary from 3.506 (1) to 3.870 (2) Å], forming a three-dimensional structure.

scholarly journals Crystal structures and conformations of two Diels–Alder adduct derivatives: 1,8-bis(thiophen-2-yl)-14-oxatetracyclo[6.5.1.02,7.09,13]tetradeca-2(7),3,5-trien-10-one and 1,8-diphenyl-14-oxatetracyclo[6.5.1.02,7.09,13] tetradeca-2,4,6-trien-10-one

2015 ◽  
Vol 71 (2) ◽  
pp. 213-216
Author(s):  
S. Gopinath ◽  
P. Narayanan ◽  
K. Sethusankar ◽  
Meganathan Nandakumar ◽  
Arasambattu K. Mohanakrishnan
Keyword(s):  
Crystal Packing ◽  
Rotation Axis ◽  
Alder Reaction ◽  
Ring System ◽  
Diels Alder ◽  
Compound I ◽  
Diels Alder Reaction ◽  
Phenyl Rings ◽  
Axis Parallel ◽  
Alder Adduct

The title compounds, C21H16O2S2(I) and C25H20O2(II), are products of a tandem `pincer' Diels–Alder reaction consisting of [2 + 2] cycloadditions between benzo[c]furan and cyclopentanone. Each comprises a fused tetracyclic ring system containing two five-membered rings (inenvelopeconformations with the O atom as the flap) and six-membered rings (inboatconformations). In addition, two thiophene rings in (I) and two phenyl rings in (II) are attached to the tetracyclic ring system. The cyclopentanone ring adopts atwistedconformation in (I) and anenvelopeconformation in (II). In (I), the thiophene rings are positionally disordered over two sets of sites, with occupancy ratios of 0.901 (2):0.099 (2) and 0.666 (2):0.334 (2). In (II), the oxygen atom of the cyclopentanone ring is rotationally disordered over two sites with an occupancy ratio of 0.579 (4):0.421 (4). The molecular structure of (I) is stabilized by an intramolecular C—H...O hydrogen bond, which generates anS(7) ring motif. In the crystal, the molecules are linkedviaweak C—H...O hydrogen bonds, which generateR22(16) ring motifs in (I) andC(8) chains in (II). In both structures, the crystal packing also features C—H...π interactions. The crystal studied of compound (I) was twinned by non-merohedry. The twin component is related by the twin law [−1 0 0 −0.101 1 −0.484 0 0 −1] operated by a twofold rotation axis parallel to thebaxis. The structure of (I) was refined with a twin scale factor of 0.275 (2).

scholarly journals Crystal structures of {[Cu(Lpn)2][Fe(CN)5(NO)]·H2O}nand {[Cu(Lpn)2]3[Cr(CN)6]2·5H2O}n[where Lpn = (R)-propane-1,2-diamine]: two heterometallic chiral cyanide-bridged coordination polymers

2015 ◽  
Vol 71 (4) ◽  
pp. 392-397
Author(s):  
Olha Sereda ◽  
Helen Stoeckli-Evans
Keyword(s):  
Hydrogen Bonds ◽  
Coordination Polymers ◽  
Three Dimensional ◽  
Water Molecules ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Compound I ◽  
Distorted Octahedral ◽  
Coordination Spheres ◽  
Compound Ii

The title compounds,catena-poly[[[bis[(R)-propane-1,2-diamine-κ2N,N′]copper(II)]-μ-cyanido-κ2N:C-[tris(cyanido-κC)(nitroso-κN)iron(III)]-μ-cyanido-κ2C:N] monohydrate], {[Cu(Lpn)2][Fe(CN)5(NO)]·H2O}n, (I), and poly[[hexa-μ-cyanido-κ12C:N-hexacyanido-κ6C-hexakis[(R)-propane-1,2-diamine-κ2N,N′]dichromium(III)tricopper(II)] pentahydrate], {[Cu(Lpn)2]3[Cr(CN)6]2·5H2O}n, (II) [where Lpn = (R)-propane-1,2-diamine, C3H10N2], are new chiral cyanide-bridged bimetallic coordination polymers. The asymmetric unit of compound (I) is composed of two independent cation–anion units of {[Cu(Lpn)2][Fe(CN)5)(NO)]} and two water molecules. The FeIIIatoms have distorted octahedral geometries, while the CuIIatoms can be considered to be pentacoordinate. In the crystal, however, the units align to form zigzag cyanide-bridged chains propagating along [101]. Hence, the CuIIatoms have distorted octahedral coordination spheres with extremely long semicoordination Cu—N(cyanido) bridging bonds. The chains are linked by O—H...N and N—H...N hydrogen bonds, forming two-dimensional networks parallel to (010), and the networks are linkedviaN—H...O and N—H...N hydrogen bonds, forming a three-dimensional framework. Compound (II) is a two-dimensional cyanide-bridged coordination polymer. The asymmetric unit is composed of two chiral {[Cu(Lpn)2][Cr(CN)6]}−anions bridged by a chiral [Cu(Lpn)2]2+cation and five water molecules of crystallization. Both the CrIIIatoms and the central CuIIatom have distorted octahedral geometries. The coordination spheres of the outer CuIIatoms of the asymmetric unit can be considered to be pentacoordinate. In the crystal, these units are bridged by long semicoordination Cu—N(cyanide) bridging bonds forming a two-dimensional network, hence these CuIIatoms now have distorted octahedral geometries. The networks, which lie parallel to (10-1), are linkedviaO—H...O, O—H...N, N—H...O and N—H...N hydrogen bonds involving all five non-coordinating water molecules, the cyanide N atoms and the NH2groups of the Lpn ligands, forming a three-dimensional framework.

scholarly journals Crystal structure of (E)-N-{2-[2-(4-methylbenzylidene)hydrazin-1-yl]-2-oxoethyl}-p-toluenesulfonamide

2015 ◽  
Vol 71 (6) ◽  
pp. 730-733 ◽  
Author(s):  
H. Purandara ◽  
Sabine Foro ◽  
B. Thimme Gowda
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Dihedral Angles ◽  
Asymmetric Unit ◽  
Acid Moiety ◽  
Torsion Angles ◽  
Centroid Distance ◽  
Benzene Rings ◽  
Amino Acid Moiety ◽  
Phenyl Rings

The title acylhydrazone derivative, C17H19N3O3S, containing an amino acid moiety and electron-donating substituents attached to both the phenyl rings, crystallized with two independent molecules (AandB) in the asymmetric unit. The molecules are bent at the S atom, with C—SO2—NH—CH2torsion angles of −67.3 (2) and 67.7 (3)° in moleculesAandB, respectively. Further, the dihedral angles between the sulfonylglycine segments and thep-toluenesulfonyl rings are 76.1 (1) and 85.8 (1)° in moleculesAandB, respectively. The central hydrazone segments and the toluene rings attached to them are almost co-planar with their mean planes being inclined to one another by 5.2 (2) (moleculeA) and 2.9 (2)° (moleculeB). The dihedral angles between the benzene rings are 86.83 (12) (moleculeA) and 74.00 (14)° (moleculeB). In the crystal, theAmolecules are linked by a pair of N—H...O hydrogen bonds, forming inversion dimers with anR22(8) ring motif. The dimers are linkedviathree N—H...O hydrogen bonds involving theBmolecules, forming chains along [100] and enclosingR22(12) andR44(16) ring motifs. The chains are linkedviaC—H...O hydrogen bonds and a C—H...π interaction, forming sheets parallel to (010). There is a further C—H...π interaction and a slipped parallel π–π interaction [inter-centroid distance = 3.8773 (16) Å] between the sheets, leading to the formation of a three-dimensional framework.

scholarly journals (S)-2-[(4-Fluorophenyl)formamido]-3-phenylpropanoic acid

IUCrData ◽  
2020 ◽  
Vol 5 (7) ◽  
Author(s):  
Kathleen S. Lee ◽  
Luke Turner ◽  
Cynthia B. Powell ◽  
Eric W. Reinheimer
Keyword(s):  
Hydrogen Bonding ◽  
Title Compound ◽  
Phenyl Ring ◽  
Room Temperature ◽  
Solid Phase ◽  
Independent Molecule ◽  
Asymmetric Unit ◽  
Torsion Angles ◽  
Compound C ◽  
Independent Molecules

The title compound, C16H14FNO3, was synthesized via solid phase methods; it exhibits monoclinic (P21) symmetry at room temperature. The two independent molecules that comprise the asymmetric unit display distinct torsion angles of 173.2 (2) and 72.6 (2)° along the central sp 3 C—N bond. In the crystal, hydrogen bonding through N—H...O contacts couples the asymmetric unit molecules into pairs that align in layers extending parallel to (100) via additional O—H...O interactions. The phenyl ring of one independent molecule was found to be disordered over two sets of sites in a 0.55 (3):0.45 (3) ratio.

Zolmitriptan oxalate and zolmitriptan camphorsulfonate: the first structural study of salt complexes of the antimigraine drug zolmitriptan

2013 ◽  
Vol 69 (10) ◽  
pp. 1186-1191
Author(s):  
Balasubramanian Sridhar ◽  
Krishnan Ravikumar ◽  
Venkatasubramanian Hariharakrishnan
Keyword(s):  
Structural Study ◽  
Three Dimensional ◽  
Helical Chain ◽  
Side Chain ◽  
Indole Ring ◽  
Asymmetric Unit ◽  
Compound I ◽  
Space Group ◽  
Compound Ii ◽  
Ring Motif

Zolmitriptan hydrogen oxalate [(S)-dimethyl(2-{5-[(2-oxo-1,3-oxazolidin-4-yl)methyl]-1H-indol-3-yl}ethyl)azanium hydrogen oxalate], C16H22N3O2+·C2HO4−, (I), and zolmitriptan camphorsulfonate [(S)-dimethyl(2-{5-[(2-oxo-1,3-oxazolidin-4-yl)methyl]-1H-indol-3-yl}ethyl)azanium (S,R)-{2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}methanesulfonate], C16H22N3O2+·C10H15O4S−, (II), are the first reported salt complexes of the antimigraine drug zolmitriptan. Compound (I) crystallizes in the space groupP21with two molecules of protonated zolmitriptan and two oxalate monoanions in the asymmetric unit, while compound (II) crystallizes in the space groupP212121with one protonated zolmitriptan molecule and one camphorsulfonate anion in the asymmetric unit. The orientations of the ethylamine side chain and the oxazolidinone ring with respect to the indole ring of the zolmitriptan cation are different for (I) and (II). In (I), they are oriented in opposite directions and the molecule adopts a step-like appearance, while in (II) the corresponding side chains are folded in the same direction, giving the molecule a cup-like appearance. The zolmitriptan molecules of (I) form anR22(8) dimer, while in (II) they form a helical chain with aC(11) motif. The oxalate monoanions of (I) interact with the zolmitriptan cations and extend the dimer into a three-dimensional hydrogen-bonded network. In (II), the camphorsulfonate anion forms anR22(15) ring motif with the zolmitriptan cation.

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