scholarly journals Three tetracyclic dibenzoazepine derivatives exhibiting different molecular conformations, different patterns of intermolecular hydrogen bonding and different modes of supramolecular aggregation

2017 ◽  
Vol 73 (1) ◽  
pp. 28-35
Author(s):  
Jeferson B. Mateus-Ruíz ◽  
Lina M. Acosta Quintero ◽  
Alirio Palma ◽  
Mario A. Macías ◽  
Justo Cobo ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Membered Ring ◽  
Boat Conformation ◽  
Compound I ◽  
Molecular Conformations ◽  
Space Group ◽  
Major Form ◽  
Biological Potential ◽  
Centrosymmetric Dimers ◽  
Twist Boat

The biological potential of compounds of the tricyclic dibenzo[b,e]azepine system has resulted in considerable synthetic efforts to develop efficient methods for the synthesis of new derivatives of this kind. (9RS,15RS)-9-Ethyl-11-methyl-9,13b-dihydrodibenzo[c,f]thiazolo[3,2-a]azepin-3(2H)-one, C19H19NOS, (I), crystallizes as a kryptoracemate with Z′ = 2 in the space group P21, with one molecule each of the (9R,15R) and (9S,15S) configurations in the asymmetric unit, while (9RS,15RS)-9-ethyl-7,12-dimethyl-9,13b-dihydrodibenzo[c,f]thiazolo[3,2-a]azepin-3(2H)-one, C20H21NOS, (II), crystallizes with Z′ = 1 in the space group C2/c. Ethyl (13RS)-2-chloro-13-ethyl-4-oxo-8,13-dihydro-4H-benzo[5,6]azepino[3,2,1-ij]quinoline-5-carboxylate, C22H20ClNO3, (III), exhibits enantiomeric disorder in the space group P\overline{1} such that the reference site is occupied by the 13R and 13S enantiomers, with occupancies of 0.900 (6) and 0.100 (6). In each of the two independent molecules in (I), the five-membered ring adopts an envelope conformation, but the corresponding ring in (II) adopts a half-chair conformation, while the six-membered ring in the major form of (III) adopts a twist-boat conformation. The conformation of the seven-membered ring in each of (I), (II) and the major form of (III) approximates to the twist-boat form. The molecules of compound (I) are linked by two C—H...O hydrogen bonds to form two independent antiparallel C(5) chains, with each type containing only one enantiomer. These chains are linked into sheets by two C—H...π(arene) hydrogen bonds, in which the two donors are both provided by the (9R,15R) enantiomer and the two acceptor arene rings form part of a molecule of (9S,15S) configuration, precluding any additional crystallographic symmetry. The molecules of compound (II) are linked by inversion-related C—H...π(arene) hydrogen bonds to form isolated cyclic centrosymmetric dimers. The molecules of compound (III) are linked into cyclic centrosymmetric dimers by C—H...O hydrogen bonds and these dimers are linked into chains by a π–π stacking interaction. Comparisons are made with some related structures.

Two seven-membered heterocycles with 1,2-diaza ring N atoms: 3,5,7-triphenyl-1,2-diazacyclohepta-1(7),2-diene and 3,7-bis(2-hydroxyphenyl)-5-phenyl-1,2-diazacyclohepta-1(7),2-diene

2013 ◽  
Vol 69 (10) ◽  
pp. 1177-1180 ◽  
Author(s):  
Yao-Cheng Shi ◽  
Hong-Yang Duan
Keyword(s):  
Hydrogen Bonds ◽  
Boat Conformation ◽  
Stacking Interactions ◽  
Asymmetric Unit ◽  
Compound I ◽  
Space Group ◽  
Π Interactions ◽  
Phenyl Rings ◽  
Independent Molecules ◽  
Twist Boat

The title compounds, 3,5,7-triphenyl-1,2-diazacyclohepta-1(7),2-diene, C23H20N2, (I), and 3,7-bis(2-hydroxyphenyl)-5-phenyl-1,2-diazacyclohepta-1(7),2-diene, C23H20N2O2, (II), constitute the first structurally characterized examples of seven-membered heterocycles with 1,2-diaza ring N atoms. Compound (I) crystallizes in the space groupP\overline{1}, with two independent molecules in the asymmetric unit that differ in the conformation of one of the phenyl rings, while (II) crystallizes in the space groupC2/c. The C5N2ring in each of (I) and (II) adopts a twist-boat conformation. Compound (I) exhibits neither C—H...π interactions nor π–π stacking interactions, whereas (II) shows both intramolecular O—H...N hydrogen bonds and a C—H...π interaction that joins the molecules into an infinite chain in the [010] direction.

scholarly journals (1S,2R,3S,6S,7R)-3,7,11,11-Tetramethyl-6,7-epoxybicyclo[5.4.0]undecane-2-ol

2014 ◽  
Vol 70 (5) ◽  
pp. o595-o595
Author(s):  
Mohamed Loubidi ◽  
Ahmed Benharref ◽  
Lahcen El Ammari ◽  
Mohamed Saadi ◽  
Moha Berraho
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Membered Ring ◽  
Boat Conformation ◽  
Axis Direction ◽  
Cedrus Atlantica ◽  
Compound C ◽  
Twist Boat

The title compound, C15H26O2, was synthesized from β-himachalene (3,5,5,9-tetramethyl-2,4a,5,6,7,8-hexahydro-1H-benzocycloheptene), which was isolated from the Atlas cedar (cedrus atlantica). The molecule is built up from a seven-membered ring to which a six- and a three-membered ring are fused. The seven- and six-membered rings each have a twist-boat conformation. In the crystal, O—H...O hydrogen bonds link the molecules into zigzag chains running along theb-axis direction.

scholarly journals (1S,2R,8R)-11-Amino-2,2-dichloro-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodec-10-en-9-one

IUCrData ◽  
2017 ◽  
Vol 2 (2) ◽  
Author(s):  
Mustapha Ait Elhad ◽  
Ahmed Benharref ◽  
Lahcen El Ammari ◽  
Mohamed Saadi ◽  
Abdelouahd Oukhrib ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Membered Ring ◽  
Monoclinic Space Group ◽  
Boat Conformation ◽  
Asymmetric Unit ◽  
Space Group ◽  
Axis Direction ◽  
Compound C ◽  
Independent Molecules

The title compound, C16H23Cl2NO, crystallizes in the monoclinic space groupP21with two independent molecules (AandB) in the asymmetric unit. They have essentially the same conformation. Each molecule is built up from fused six- and seven-membered rings and an additional three-membered ring. The six-membered ring has an envelope conformation, with the C atom belonging to the three-membered ring forming the flap, while the seven-membered ring displays a boat conformation. In the crystal, molecules are linked into chains propagating along thea-axis direction by N—H...O hydrogen bonds.

Synthesis and Structure of the Helicate (M)-(–)-[Pt2 {(R,R)-tetraphos}2](CF3SO3)4 · 4.5 H2O

2004 ◽  
Vol 59 (11-12) ◽  
pp. 1458-1461
Author(s):  
Heather J. Kitto ◽  
A. David Rae ◽  
Anthony C. Willis ◽  
Johann Zank ◽  
S. Bruce Wild
Keyword(s):  
Membered Ring ◽  
Boat Conformation ◽  
Fold Axis ◽  
Space Group ◽  
Independent Molecules ◽  
Α Helix ◽  
Twist Boat

The complex (M)-(-)-[Pt2{(R,R)-tetraphos}2](CF3SO3)4 · 4.5 H2O, where tetraphos = 1,1,4,7, 10,10-hexaphenyl-1,4,7,10-tetraphosphadecane, has been isolated and structurally characterized. The compound crystallizes in the space group C2 with two crystallographically different, but very similar, cations in the structure, each of which contains a 2-fold axis coincident with the crystallographic 2-fold axis. Each independent cation of the salt consists of a double-stranded, diplatinum(II) helicate that completes a ca. one-eighth turn of a double α-helix in the M direction, as evidenced by the angle between the two, non-orthogonal PtP4 square planes in each of the independent molecules. A feature of the structures is the 10-membered ring containing the two platinum atoms and the four chiral phosphorus stereocentres of R configuration; this ring has a distorted twist-boat-chair-boat conformation of λ helicity, which is responsible for the M twist of the helicate.

scholarly journals Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supramoleular assembly mediated by C—H...π and C—Br...π interactions

2017 ◽  
Vol 73 (2) ◽  
pp. 115-120 ◽  
Author(s):  
Marisiddaiah Girisha ◽  
Belakavadi K. Sagar ◽  
Hemmige S. Yathirajan ◽  
Ravindranath S. Rathore ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Active Sites ◽  
Unit Cell ◽  
Stacking Interactions ◽  
Compound I ◽  
Space Group ◽  
Π Interactions ◽  
Π Stacking ◽  
Compound Ii ◽  
Centrosymmetric Dimers

It has been observed that when electron-rich naphthyl rings are present in chalcones they can participate in π–π stacking interactions, and this can play an important role in orientating inhibitors within the active sites of enzymes, while chalcones containing heterocyclic substituents additionally exhibit fungistatic and fungicidal properties. With these considerations in mind, three new chalcones containing 2-naphthyl substituents were prepared. 3-(4-Fluorophenyl)-1-(naphthalen-2-yl)prop-2-en-1-one, C19H13FO, (I), crystallizes withZ′ = 2 in the space groupP-1 and the four molecules in the unit cell adopt an arrangement which resembles that in the space groupP21/a. Although 3-(4-bromophenyl)-1-(naphthalen-2-yl)prop-2-en-1-one, C19H13BrO, (II), withZ′ = 1, is not isostructural with (I), the molecules of (I) and (II) adopt very similar conformations. In 1-(naphthalen-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one, C17H12OS, (III), the thiophene unit is disordered over two sets of atomic sites, with occupancies of 0.780 (3) and 0.220 (3), which are related by a near 180° rotation of the thiophene unit about its exocyclic C—C bond. The molecules of compound (I) are linked by three independent C—H...π(arene) hydrogen bonds to form centrosymmetric octamolecular aggregates, whereas the molecules of compound (II) are linked into molecular ladders by a combination of C—H...π(arene) and C—Br...π(arene) interactions, and those of compound (III) are linked into centrosymmetric dimers by C—H...π(thiophene) interactions.

scholarly journals 1-Isobutyl-8,9-dimethoxy-3-phenyl-5,6-dihidroimidazo[5,1-a]isoquinolin-2-ium chloride

IUCrData ◽  
2019 ◽  
Vol 4 (10) ◽  
Author(s):  
R. Ya. Okmanov ◽  
D. B. Tukhtaev ◽  
A. Sh. Saidov ◽  
B. Tashkhodjaev
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Boat Conformation ◽  
Phosphoryl Chloride ◽  
Molecular Salt ◽  
Centrosymmetric Dimers ◽  
Twist Boat

The molecular salt, C23H26N2O2 +·Cl−, was obtained from 1-isobutyl-8,9-dimethoxy-3-phenyl-5,6-dihydroimidazo[5,1-a]isoquinoline, which was synthesized by cyclocondensation of α-benzoylamino-γ-methyl-N-[2-(3,4-dimethoxyphenyl)ethyl]valeramide in the presence of phosphoryl chloride. The tetrahydropyridine ring adopts a twist–boat conformation. In the crystal structure, centrosymmetric dimers are formed by N—H...Cl and C—H...Cl hydrogen bonds.

scholarly journals Ethyl 2,6-bis(4-chlorophenyl)-1-isocyano-4-oxocyclohexanecarboxylate

2014 ◽  
Vol 70 (7) ◽  
pp. o802-o802
Author(s):  
Dawei Zhang ◽  
Peng Yang ◽  
Wei Liu ◽  
Jing Li
Keyword(s):  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Title Compound ◽  
Membered Ring ◽  
Boat Conformation ◽  
Equatorial Position ◽  
Aryl Group ◽  
Compound C ◽  
Twist Boat

In the title compound, C22H19Cl2NO3, the central six-membered ring is in a twist-boat conformation. The two aryl groups are in equatorial positions,transto each other and with a dihedral angle of 77.50 (2)° between them. One of the least hindered –CH2– groups and one of the aryl-substituted C atoms, with its axial H atom, are in the flagpole positions. The ethoxycarbonyl group is in an equatorial position and iscisto the second aryl group. In the crystal, molecules are linkedviaweak C—H...O hydrogen bonds, forming chains along [010].

scholarly journals (3S)-3,8-Dibromo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazapin-2-one

IUCrData ◽  
2017 ◽  
Vol 2 (3) ◽  
Author(s):  
Abdelhanine Essaghouani ◽  
Mohammed Boulhaoua ◽  
Sanae Lahmidi ◽  
Mohamed Mokhtar Mohamed Abdelahi ◽  
El Mokhtar Essassi ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Membered Ring ◽  
Boat Conformation ◽  
Compound C ◽  
Π Stacking ◽  
Centrosymmetric Dimers

In the title compound, C15H10Br2N2O, one Br atom is disordered over two non-chemically equivalent sites, and as a consequence, the crystallized sample contains a mixture of isomers, viz. 98.4% of 3,8-dibromo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazapin-2-one and 1.6% of 3,6-dibromo-4-phenyl-2,3-dihydro-1H-1,5-benzodiazapin-2-one. The seven-membered ring adopts a boat conformation. In the crystal, pairwise N—H...O hydrogen bonds form centrosymmetric dimers, which are associated in the crystal through a combination of π–π stacking and C—H...π(ring) interactions.

scholarly journals Crystal structure of 16-hydroxy-4,4,10,13,14-pentamethyl-17-(6-methylhept-5-en-2-yl)-4,5,6,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

2015 ◽  
Vol 71 (7) ◽  
pp. o464-o465 ◽  
Author(s):  
Jun-Jun Ge ◽  
Pian Chen ◽  
Xiao-Xia Ye
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Chair Conformation ◽  
Membered Ring ◽  
Boat Conformation ◽  
Carbonyl Groups ◽  
Compound C ◽  
Cyclohexene Ring ◽  
Supramolecular Chains ◽  
Twist Boat

The title compound, C30H48O2, contains a fused four-ring triterpenoid system. In the molecule, the two cyclohexane rings adopt a chair conformation and a twist boat conformation, respectively, the central cyclohexene ring adopts a half-chair conformation whereas the five membered ring adopts an envelope conformation. In the crystal, O—H...O hydrogen bonds between the hydroxy and carbonyl groups of adjacent molecules link the molecules into supramolecular chains propagating along theb-axis direction.

scholarly journals Crystal structure of ethyl 2-methyl-5,10-dioxo-4-phenyl-5,10-dihydro-4H-11-thia-1,4a-diazabenzo[b]fluorene-3-carboxylate

2018 ◽  
Vol 74 (2) ◽  
pp. 124-126
Author(s):  
Yegor Yartsev ◽  
Pavel Lyubashov ◽  
Vyacheslav Povstyanoy ◽  
Mykhailo Povstyaniy ◽  
Iryna Lebedyeva
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Chiral Center ◽  
Thiazole Ring ◽  
Boat Conformation ◽  
Space Group ◽  
Π Interactions ◽  
Compound C ◽  
Twist Boat

The title compound, C24H18N2O4S, crystallizes in the orthorhombic P212121 space group, indicating the existence of only one enantiomer with an S configuration of the chiral center in the crystal phase. The dihydropyrimidine ring adopts a twist-boat conformation while the quinone ring is slightly non-planar. In the crystal, molecules are linked by weak C—H...O and C—H...S hydrogen bonds and C—H...π interactions. In addition, a short intermolecular S...N contact of 3.250 (3) Å indicates an interaction between the S atom and the π-system of the thiazole ring.

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