Structural similarities among eight benzoylhydrazones

2014 ◽  
Vol 70 (9) ◽  
pp. 912-919
Author(s):  
Quoc Cuong Ton ◽  
Michael Bolte ◽  
Ernst Egert
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Phenyl Ring ◽  
Molecular Conformation ◽  
Solvent Molecule ◽  
Amide Group ◽  
Benzoyl Group ◽  
Independent Molecules

The crystal structures of eight benzoylhydrazones with different substituents have been investigated, namely 1-benzoyl-2-(propan-2-ylidene)hydrazone, C10H12N2O, (I), 1-benzoyl-2-(1-cyclohexylethylidene)hydrazone, C15H20N2O, (II), 1-benzoyl-2-[1-(naphthalen-2-yl)ethylidene]hydrazone, C19H16N2O, (III), 1-benzoyl-2-(1-cyclohexylbenzylidene)hydrazone, C20H22N2O, (IV), 1-benzoyl-2-(1-phenylbenzylidene)hydrazone, C20H16N2O, (V), 1-benzoyl-2-[1-(4-chlorophenyl)benzylidene]hydrazone, C20H15ClN2O, (VI), 1-benzoyl-2-(4-hydroxybenzylidene)hydrazone methanol monosolvate, C14H12N2O2·CH3OH, (VII), and 1-benzoyl-2-(1,1-diphenylpropan-2-ylidene)hydrazone, C22H20N2O, (VIII). The ten molecules in the eight crystal structures [there are two independent molecules in the structures of (V) and (VI)] show similar conformations and hydrogen-bonding patterns. The C=N—NH—C=O group is planar, but the plane of the phenyl ring of the benzoyl group is rotated by about 30° with respect to that of the keto group [except for (IV), where the groups are coplanar]. Only in the amide group of (VIII) is the N—H groupsynto the C=O bond, whereas the seven other compounds exhibit theanticonformation. Unless prevented by steric hindrance, N—H...O hydrogen bonds help to stabilize the crystal structure, which leads to infinite chains or dimers depending upon the molecular conformation. The molecular packing is supported by intermolecular C—H...O interactions. In the crystal structure of (VII), the methanol solvent molecule participates in two strong hydrogen bonds and two weak C—H...O interactions, thus acting as a link between the molecular chains.

scholarly journals Crystal structure of 2-[(E)-4-benzyloxy-2-hydroxybenzylidene]-N-cyclohexylhydrazinecarbothioamide acetonitrile hemisolvate

2014 ◽  
Vol 70 (9) ◽  
pp. o987-o988 ◽  
Author(s):  
N. R. Sajitha ◽  
M. Sithambaresan ◽  
M. R. Prathapachandra Kurup
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Double Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Molecular Conformation ◽  
Solvent Molecule ◽  
Asymmetric Unit ◽  
Compound C ◽  
Independent Molecules

The asymmetric unit of the title compound, C21H25N3O2S·0.5C2H3N, contains two independent molecules with almost similar structural properties along with a solvent molecule of acetonitrile. The compound exists in theEconformation with respect to the azomethine C=N double bond. The hydrazinecarbothioamide moieties in both independent molecules are almost planar [maximum deviations of 0.013 (2) and 0.007 (2) Å]. The molecular conformation is stabilized in each case by an intramolecular N—H...N hydrogen bond. In the crystal, pairs of N—H...S hydrogen bonds link each of the independent molecules into inversion dimers. The dimers are interconnected by means of three C—H...π interactions.

scholarly journals Crystal structures of 2-[3,5-bis(bromomethyl)-2,4,6-triethylbenzyl]isoindoline-1,3-dione and 2-{5-(bromomethyl)-3-[(1,3-dioxoisoindolin-2-yl)methyl]-2,4,6-triethylbenzyl}isoindoline-1,3-dione

2021 ◽  
Vol 77 (9) ◽  
Author(s):  
Manuel Stapf ◽  
Betty Leibiger ◽  
Anke Schwarzer ◽  
Monika Mazik
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Molecular Conformation ◽  
Halogen Bond ◽  
Asymmetric Unit ◽  
Space Group ◽  
Π Interactions ◽  
Hydrogen Bonding Interactions

The title compounds, C23H25Br2NO2 (1) and C31H29BrN2O4 (2), crystallize in the space group P21/n with two (1-A and 1-B) and one molecules, respectively, in the asymmetric unit of the cell. The molecular conformation of these compounds is stabilized by intramolecular C—H...O hydrogen bonds and C—H...N or C—H...π interactions. The crystal structure of 1 features a relatively strong Br...O=C halogen bond, which is not observed in the case of 2. Both crystal structures are characterized by the presence of C—H...Br hydrogen bonds and numerous intermolecular C—H...O hydrogen-bonding interactions.

scholarly journals Crystal structure of 2-hydroxy-2-phenylacetophenone oxime

2021 ◽  
Vol 77 (1) ◽  
pp. 66-69
Author(s):  
Nurcan Akduran
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Phenyl Ring ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Oxime Group ◽  
Phenyl Rings ◽  
Ring Interaction ◽  
Van Der Waals Contacts

The title compound [systematic name: 2-(N-hydroxyimino)-1,2-diphenylethanol], C14H13NO2, consists of hydroxy phenylacetophenone and oxime units, in which the phenyl rings are oriented at a dihedral angle of 80.54 (7)°. In the crystal, intermolecular O—HOxm...NOxm, O—HHydr...OHydr, O—H′Hydr...OHydr and O—HOxm...OHydr hydrogen bonds link the molecules into infinite chains along the c-axis direction. π–π contacts between inversion-related of the phenyl ring adjacent to the oxime group have a centroid–centroid separation of 3.904 (3) Å and a weak C—H...π(ring) interaction is also observed. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (58.4%) and H...C/C...H (26.4%) contacts. Hydrogen bonding and van der Waals contacts are the dominant interactions in the crystal packing.

scholarly journals Crystal structure of {2,2′-[ethylenebis(nitrilomethanylylidene)]diphenolato-κ4O,N,N′,O′}oxidovanadium(IV) methanol monosolvate

2014 ◽  
Vol 70 (11) ◽  
pp. m380-m381
Author(s):  
Rachel E. Hsuan ◽  
Jemma E. Hughes ◽  
Thomas H. Miller ◽  
Nabila Shaikh ◽  
Phoebe H. M. Cunningham ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Basal Plane ◽  
Solvent Molecule ◽  
Vanadium Atom ◽  
Asymmetric Unit ◽  
Extended Structure ◽  
Independent Molecules ◽  
Ethylenediamine Ligand

Two independent molecules of the title solvated complex, [V(C16H14N2O2)O]·CH3OH, also known as [N,N′-bis(salicylidene)ethylenediamine]oxidovanadium(IV) or vanadyl salen, crystallize in the asymmetric unit. Each disordered methanol solvent molecule [occupancy ratios 0.678 (4):0.322 (4) and 0.750 (5):0.250 (5)] is linked to a [N,N′-bis(salicylidene)ethylenediamine]oxidovanadium(IV) molecule by an O—H...O hydrogen bond and to others by C—H...O hydrogen bonds. The resulting extended structure consists of a bilayer of molecules parallel to theabplane. Despite the fact that solvates are common in complexes derived from substituted analogues of theN,N′-bis(salicylidene)ethylenediamine ligand, the title solvate is the first one of [N,N′-bis(salicylidene)ethylenediamine]oxidovanadium(IV) to be structurally characterized. The two vanadyl species have very similar internal geometries, which are best characterized as distorted square-based pyramidal with the vanadium atom displaced from the N2O2basal plane by 0.5966 (9) Å in the direction of the doubly-bonded oxide ligand.

scholarly journals 4-Chloro-N-methylbenzamide

2012 ◽  
Vol 68 (4) ◽  
pp. o937-o937
Author(s):  
Juan Yuan ◽  
Yan-Ju Liu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Title Compound ◽  
Amide Group ◽  
Dihedral Angles ◽  
Asymmetric Unit ◽  
Compound C ◽  
Independent Molecules

There are two molecules in the asymmetric unit of the title compound, C8H8ClNO, which are linked in the crystal structureviaN—H...O hydrogen bonds into chains along thebaxis. C—H...O contacts also occur. The benzene ring makes dihedral angles of 5.9 (1) and 16.7 (1)°with the attached amide group in the two independent molecules.

Crystal structures of 7-azaindole, an unusual hydrogen-bonded tetramer, and of two of its methylmercury(II) complexes

1990 ◽  
Vol 68 (1) ◽  
pp. 193-201 ◽  
Author(s):  
Pascal Dufour ◽  
Yves Dartiguenave ◽  
Michèle Dartiguenave ◽  
Nathalie Dufour ◽  
Anne-Marie Lebuis ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Nitrogen Atom ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Membered Ring ◽  
Pyridine Nitrogen Atom ◽  
Nitrate Ions ◽  
Pyridine Nitrogen ◽  
Independent Molecules ◽  
Hydrogen Bonded

Crystals of 7-azaindole ([Formula: see text], a = 11.312(4), b = 14.960(6), c = 15.509(5) Å, α = 102.86(3), β = 108.78(3), γ = 90.71(3)°, Z = 16, R = 0.052) contain tetrameric units of approximate S4 symmetry, in which the molecules are associated by means of four complementary N—H … N hydrogen bonds. [CH3Hg(7-azaindole)]NO3 ([Formula: see text], a = 7.818(3), b = 7.884(3), c = 9.135(4) Å, α = 97.89(3), β = 109.13(3), γ = 103.28(3)°, Z = 2, R = 0.039) contains well-separated nitrate ions and complex cations in which the methylmercury group is linearly bonded to the pyridine nitrogen atom, whereas the five-membered ring remains protonated. In the neutral [CH3Hg(azaindolate)] complex ([Formula: see text], a = 10.926(10), b = 11.333(8), c = 11.647(10) Å, α = 92.13(8), β = 104.83(9), γ = 111.86(7)°, Z = 6, R = 0.048), methylmercury groups have substituted the N—H proton in the five-membered ring for the three symmetry-independent molecules. Intermolecular secondary Hg … N bonds are found with pyridine nitrogens. Keywords: azaindole, methylmercury, crystal structure.

scholarly journals Crystal structure of 2-[(E)-2-(2-chlorobenzylidene)hydrazin-1-yl]-4-phenyl-1,3-thiazole

2014 ◽  
Vol 70 (9) ◽  
pp. o907-o908 ◽  
Author(s):  
Joel T. Mague ◽  
Shaaban K. Mohamed ◽  
Mehmet Akkurt ◽  
Alaa A. Hassan ◽  
Mustafa R. Albayati
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Phenyl Ring ◽  
Thiazole Ring ◽  
Dihedral Angles ◽  
Asymmetric Unit ◽  
Compound C ◽  
Independent Molecules ◽  
Supramolecular Chains

The asymmetric unit of the title compound, C16H12ClN3S, contains two independent molecules whose conformations differ primarily in the orientations of the phenyl and chlorobenzene rings with respect to the thiazole ring. In the first molecule, the dihedral angles are 3.0 (1) and 9.2 (1)°, respectively, for the phenyl ring and the chlorobenzene ring, while in the second molecule, the corresponding angles are 18.6 (1) and 23.4 (1)°. In the crystal, the two independent molecules are associatedviacomplementary N—H...N hydrogen bonds into a dimer. These dimers are associated through weak C—H...Cl and C—H...S interactions into supramolecular chains propagating along thea-axis direction.

scholarly journals Crystal structure of 5-amino-5′-chloro-6-(4-chlorobenzoyl)-8-nitro-2,3-dihydro-1H-spiro[imidazo[1,2-a]pyridine-7,3′-indolin]-2′-one including an unknown solvent molecule

2014 ◽  
Vol 70 (9) ◽  
pp. o971-o972
Author(s):  
R. A. Nagalakshmi ◽  
J. Suresh ◽  
S. Sivakumar ◽  
R. Ranjith Kumar ◽  
P. L. Nilantha Lakshman
Keyword(s):  
Hydrogen Bonds ◽  
Solvent Molecule ◽  
Asymmetric Unit ◽  
Acta Cryst ◽  
Compound C ◽  
Benzoyl Group ◽  
Independent Molecules ◽  
Solvent Molecules ◽  
Intramolecular Hydrogen ◽  
Ring Motif

The asymmetric unit of the title compound, C21H15Cl2N5O4, contains two independent molecules (AandB) having similar conformations. The amine (NH2) group forms an intramolecular hydrogen bond with the benzoyl group, giving anS(6) ring motif in both molecules. The central six-membered rings adopt sofa conformations and the imidazole rings are planar (r.m.s deviations = 0.0150 and 0.0166 Å). The pyridine and imidazole rings are inclined to one another by 3.54 (1) and 3.03 (1)° in moleculesAandB, respectively. In the crystal, molecules are linked by N—H...O hydrogen bonds, forming chains along theaaxis which encloseR22(16) ring motifs. The rings are linked by weak N—H...O and C—H...O hydrogen bonds and C—H...π interactions forming sheets lying parallel to (001). A region of disordered electron density, most probably disordered solvent molecules, occupying voids ofca753 Å3for an electron count of 260, was treated using the SQUEEZE routine inPLATON[Spek (2009).Acta Cryst.D65, 148–155]. Their formula mass and unit-cell characteristics were not taken into account during refinement.

scholarly journals The crystal structure of 1-(2-hydroxy-5-methoxyphenyl)ethanone 4,4-dimethylthiosemicarbazone

2015 ◽  
Vol 71 (11) ◽  
pp. o811-o812
Author(s):  
Brian J. Anderson ◽  
Michael B. Freedman ◽  
Victoria A. Smolenski ◽  
Jerry P. Jasinski
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Methyl Groups ◽  
Asymmetric Unit ◽  
Compound C ◽  
Thioamide Group ◽  
The Mean ◽  
Independent Molecules ◽  
The Individual

The asymmetric unit of the title compound, C12H17N3O2S, contains two independent molecules,AandB. Both molecules are nearly planar with the dihedral angle between the mean planes of the thioamide group and benzene ring being 7.5 (1)° inAand 4.3 (2)° inB. In each molecule, the hydroxy group participates in intramolecular O—H...N hydrogen bonding, while the amino H atom is not involved in hydrogen bonding because of the steric hinderence caused by two neighboring methyl groups. In the crystal, the individual molecules are linked by weak C—H...O hydrogen bonds, formingA–AandB–Binversion dimers. The dimers are linkedviaC—H...π interactions which help stabilize the packing.

scholarly journals Crystal structures of two (±)-exo-N-isobornylacetamides

2015 ◽  
Vol 71 (10) ◽  
pp. 1117-1120 ◽  
Author(s):  
Dmitrijs Stepanovs ◽  
Daniels Posevins ◽  
Maris Turks
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Asymmetric Unit ◽  
Double Chain ◽  
Space Group ◽  
Axis Direction ◽  
Independent Molecules

The title compounds consist of a bornane skeleton with attached acetamide, C12H21NO (±)-(1) {systematic name: (±)-N-[(1RS,2RS,4RS)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]acetamide}, and chloroacetamide, C12H20ClNO (±)-(2) {systematic name: (±)-2-chloro-N-[(1RS,2RS,4RS)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl]acetamide}, functionalities to the 2-exo-position. The crystal structure of the first monoclinic polymorph of (±)-(1) has been reported previously [Unget al.(2014).Monatsh. Chem.145, 983–992]. Compound (±)-(1) crystallizes in the space groupP21/nwith two independent molecules in the asymmetric unit, in contrast to the above-mentioned polymorph which crystallized in the space groupC2/cwith one molecule in the asymmetric unit. In the title compounds, the bicyclic bornane moieties have normal geometries. In the crystals of both compounds, molecules are linked by N—H...O hydrogen bonds, reinforced by C—H...O contacts, formingtrans-amide chains propagating along thea-axis direction. In the case of compound (±)-(1), neighbouring chains are linked by further C—H...O contacts, forming double-chain ribbons along [100].

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