Crystal chemistry of tetraradial species. Part 4. Hydrogen bonding to aromatic π systems: crystal structures of fifteen tetraphenylborates with organic ammonium cations

1994 ◽  
Vol 72 (5) ◽  
pp. 1273-1293 ◽  
Author(s):  
Pradip K. Bakshi ◽  
Antony Linden ◽  
Beverly R. Vincent ◽  
Stephen P. Roe ◽  
D. Adhikesavalu ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Crystal Chemistry ◽  
Phenyl Ring ◽  
Orientational Disorder ◽  
Compromise Solutions ◽  
The Mean ◽  
General Organization

The aim of this investigation is to provide a classification and examples of N—H …π (and also O—H …π) bonds to the aromatic π systems in organic ammonium tetraphenylborates that would serve as reference for X—H …π(arene) bonds in general. To this end the crystal structures of the tetraphenylborates of the following cations have been determined: Me3NH+, Et3NH+, quinuclidinium, DabcoH+, Et(iso-Pr)2NH+ (monohydrate), (Ph3B)NH[—(CH2)2—]2NHMe+ (Me2CO solvate), Me2NH2+ (MeCN and Et2CO solvates), Et2NH2+, (iso-Pr)2NH2+, azoniacycloheptane, guanidinium (monohydrate), MeNH3+, EtNH3+, and 1-adamantammonium (monohydrate). These structures contain a variety of normal, bifurcated, and trifurcated N—H …π bonds as well as normal O—H …π bonds to the phenyl groups of the anion. The X—H …π bonds will form whenever opportunity arises, even though the result may be unfavourable bonding geometry. Branched bonds and orientational disorder represent compromise solutions in situations where the H(X) hydrogens are presented with competing phenyl acceptors or where the general organization of the crystal structure offers unfavourable bonding conditions to these hydrogens. The distributions of the distances from X or H(X) to the centre of the phenyl-ring skeleton are analyzed in detail, as are also those of the mean X … C and H(X)… C distances to the ring carbons.

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.

Aminosulfonic acids. Part 1. Crystal structures of N-methylaminomethanesulfonic acid, MeNHCH2SO3H, and disodium N-methyliminobis(methanesulfonate) dihydrate, MeN(CH2SO3Na)2•2H2O

1984 ◽  
Vol 62 (3) ◽  
pp. 540-548 ◽  
Author(s):  
T. Stanley Cameron ◽  
Walter J. Chute ◽  
Osvald Knop
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Water Molecules ◽  
Amino Group ◽  
Orientational Disorder ◽  
Space Group ◽  
Bond Lengths ◽  
Hydrogen Bonded

The crystal structure of N-methylaminomethanesulfonic acid (P212121, a = 5.455(1) Å, b = 7.791(1) Å, c = 11.925(2) Å, Z = 4) consists of +MeNH2CH2SO3− zwitterions hydrogen-bonded to form infinite chains about screw axes parallel to a. In the structure of MeN(CH2SO3Na)2•2H2O (Pbcn, a = 10.469(1) Å, b = 6.039(3) Å, c = 17.549(3) Å, Z = 4), layers of MeN(CH2SO3−)2 anions alternate with layers of Na+ ions parallel to (001). The anions are linked by [Formula: see text] bonds between the water molecules and the O(2) atoms of the sulfonate groups. Because of the twofold orientational disorder of the N—CH3 groups the space group Pbcn is only statistical.The S—C, C—N, and S—O bond lengths in solid aminosulfonic acids and their salts are discussed with a view to detecting the existence of effects due to deprotonation of the amino group and to hydrogen bonding.

scholarly journals Crystal structure ofN1-phenyl-N4-[(quinolin-2-yl)methylidene]benzene-1,4-diamine

2014 ◽  
Vol 70 (9) ◽  
pp. o905-o906 ◽  
Author(s):  
Md. Serajul Haque Faizi ◽  
Ashraf Mashrai ◽  
Saleem Garandal ◽  
M. Shahid
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Benzene Ring ◽  
Title Compound ◽  
Phenyl Ring ◽  
Bond Angle ◽  
Ring System ◽  
Dihedral Angles ◽  
Quinoline Ring ◽  
Compound C

In the title compound, C22H17N3, the dihedral angles between the central benzene ring and the terminal phenyl ring and quinoline ring system (r.m.s. deviation = 0.027 Å) are 44.72 (7) and 9.02 (4)°, respectively, and the bond-angle sum at the amine N atom is 359.9°. In the crystal, the N—H group is not involved in hydrogen bonding and the molecules are linked by weak C—H...π interactions, generating [010] chains.

Structural Studies on N-(2,4,6-Trimethylphenyl)-methyl/ chloro-acetamides, 2,4,6-(CH3)3C6H2NH-CO-CH3–yXy (X = CH3 or Cl and y = 0, 1, 2)

2006 ◽  
Vol 61 (10-11) ◽  
pp. 588-594 ◽  
Author(s):  
Basavalinganadoddy Thimme Gowda ◽  
Jozef Kožíšek ◽  
Hartmut Fuess
Keyword(s):  
Crystal Structure ◽  
Crystal Structures ◽  
Structural Data ◽  
The Other ◽  
Side Chain ◽  
Structural Studies ◽  
Asymmetric Unit ◽  
Lattice Constants ◽  
Peptide Linkage ◽  
The Mean

TMPAThe effect of substitutions in the ring and in the side chain on the crystal structure of N- (2,4,6-trimethylphenyl)-methyl/chloro-acetamides of the configuration 2,4,6-(CH3)3C6H2NH-COCH3− yXy (X = CH3 or Cl and y = 0,1, 2) has been studied by determining the crystal structures of N-(2,4,6-trimethylphenyl)-acetamide, 2,4,6-(CH3)3C6H2NH-CO-CH3 (); N-(2,4,6- trimethylphenyl)-2-methylacetamide, 2,4,6-(CH3)3C6H2NH-CO-CH2-CH3 (TMPMA); N-(2,4,6- trimethylphenyl)-2,2-dimethylacetamide, 2,4,6-(CH3)3C6H2NH-CO-CH(CH3)2 (TMPDMA) and N-(2,4,6-trimethylphenyl)-2,2-dichloroacetamide, 2,4,6-(CH3)3C6H2NH-CO-CHCl2 (TMPDCA). The crystallographic system, space group, formula units and lattice constants in Å are: TMPA: monoclinic, Pn, Z = 2, a = 8.142(3), b = 8.469(3), c = 8.223(3), β = 113.61(2)◦; TMPMA: monoclinic, P21/n, Z = 8, a = 9.103(1), b = 15.812(2), c = 16.4787(19), α = 89.974(10)◦, β = 96.951(10)◦, γ =89.967(10)◦; TMPDMA: monoclinic, P21/c, Z = 4, a =4.757(1), b= 24.644(4), c =10.785(2), β = 99.647(17)◦; TMPDCA: triclinic, P¯1, Z = 2, a = 4.652(1), b = 11.006(1), c = 12.369(1), α = 82.521(7)◦, β = 83.09(1)◦, γ = 79.84(1)◦. The results are analyzed along with the structural data of N-phenylacetamide, C6H5NH-CO-CH3; N-(2,4,6-trimethylphenyl)-2-chloroacetamide, 2,4,6-(CH3)3C6H2NH-CO-CH2Cl; N-(2,4,6-trichlorophenyl)-acetamide, 2,4,6-Cl3C6H2NH-COCH3; N-(2,4,6-trichlorophenyl)-2-chloroacetamide, 2,4,6-Cl3C6H2NH-CO-CH2Cl; N-(2,4,6-trichlorophenyl)- 2,2-dichloroacetamide, 2,4,6-Cl3C6H2NH-CO-CHCl2 and N-(2,4,6-trichlorophenyl)- 2,2,2-trichloroacetamide, 2,4,6-Cl3C6H2NH-CO-CCl3. TMPA, TMPMA and TMPDCA have one molecule each in their asymmetric units, while TMPDMA has two molecules in its asymmetric unit. Changes in the mean ring distances are smaller on substitution as the effect has to be transmitted through the peptide linkage. The comparison of the other bond parameters reveal that there are significant changes in them on substitution.

scholarly journals How cyanophage S-2L rejects adenine and incorporates 2-aminoadenine to saturate hydrogen bonding in its DNA

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Dariusz Czernecki ◽  
Pierre Legrand ◽  
Mustafa Tekpinar ◽  
Sandrine Rosario ◽  
Pierre-Alexandre Kaminski ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Active Site ◽  
Metal Ion ◽  
Restriction Endonucleases ◽  
Structural Element

AbstractBacteriophages have long been known to use modified bases in their DNA to prevent cleavage by the host’s restriction endonucleases. Among them, cyanophage S-2L is unique because its genome has all its adenines (A) systematically replaced by 2-aminoadenines (Z). Here, we identify a member of the PrimPol family as the sole possible polymerase of S-2L and we find it can incorporate both A and Z in front of a T. Its crystal structure at 1.5 Å resolution confirms that there is no structural element in the active site that could lead to the rejection of A in front of T. To resolve this contradiction, we show that a nearby gene is a triphosphohydolase specific of dATP (DatZ), that leaves intact all other dNTPs, including dZTP. This explains the absence of A in S-2L genome. Crystal structures of DatZ with various ligands, including one at sub-angstrom resolution, allow to describe its mechanism as a typical two-metal-ion mechanism and to set the stage for its engineering.

Complexes of Copper, Silver, and Gold with Urea Homologues. Crystal Structures of [{µ2-SeC(NH2)2} Ag{SeC(NH2)2}2]22+2Cl- • 4 DMF and [Ph3PAu{SC(NHMe)2}]+Cl- • SC(NHMe)2

1994 ◽  
Vol 49 (1) ◽  
pp. 21-26 ◽  
Author(s):  
Wolfgang Eikens ◽  
Peter G. Jones ◽  
Jürgen Lautner ◽  
Carsten Thöne
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Dinuclear Complex ◽  
Selenium Atom

Abstract The title compounds were prepared from chloro(organophosphine)metal(I) complexes and the urea homologues SeC(NH2)2 and SC(NHMe)2 in good yields. Recrystallization of [Ph3,PAg{SeC(NH2)2}]+Cl- from DMF/CH2Cl2 leads in low yield to the dinuclear complex [{µ2-SeC(NH2)2}Ag{SeC(NH2)2}2]22+2Cl- • 4DMF. The crystal structure reveals short Ag-Ag contacts and unexpectedly acute angles at the bridging selenium atom. The crystal structure of [Ph3PAu{SC(NHMe)2}]+Cl- • SC(NHMe)2 shows short N•••Cl and N•••S contacts that probably correspond to hydrogen bonding.

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.

Darstellung und Kristallstruktur von Tl4TiS4, TI4SnS4 und Tl4TiSe4 / Preparation and Crystal Structure of Tl4TiS4, TI4SnS4 and Tl4TiSe4

1984 ◽  
Vol 39 (6) ◽  
pp. 705-712 ◽  
Author(s):  
Kurt O. Klepp ◽  
Günther Eulenberger
Keyword(s):  
Crystal Structure ◽  
Single Crystal ◽  
Crystal Structures ◽  
Lone Electron Pair ◽  
Electron Pair ◽  
Monoclinic System ◽  
The Mean ◽  
Similar Description ◽  
Oriented Parallel ◽  
Stereochemical Activity

AbstractThe isostructural compounds Tl4TiS4, Tl4SnS4 and Tl4TiSe4 crystallize in the monoclinic system, space group P21/c with a = 8.328, b = 8.191, c = 15.248 Å, β = 104.53°; a = 8.395, b = 8.280, c = 15.398 A, ft = 103.69°, and a = 8.517, b = 8.389, c = 15.672 Å, β = 103.50°, respectively. There are four formula units in the unit cell. The crystal structures were determined and refined from single crystal diffractometer data. They are characterized by isolated tetrahedral thioanions which are connected with each other by Tl+ ions. The mean bond lengths are Ti-S = 2.26 Å, Sn-S = 2.40 Å and Ti -Se = 2.38 Å. The Tl atoms are surrounded by six and seven chalcogen atoms, respectively, in an irregular and polar arrangement, thus indicating stereochemical activity of the lone electron pair of the Tl+ ions. Tl-S distances vary from 2.93 to 3.98 Å, Tl-Se distances from 3.03 to 3.96 Å. The Tl atoms have nearest Tl neighbours at distances ranging from 3.46 to 3.65 Å. The crystal structure can be described as built from pseudotetragonal slabs oriented parallel to (001) which contain the cations and the tetrahedral anions. It is shown that a similar description is valid also for the crystal structures of Tl4GeS4 [1] and Na4SnS4 [2, 3].

Mono- and difunctional furan-based 1,2,3,5-dithiadiazolyl radicals; preparation and solid state structures of 2,5-[(S2N2C)OC4H2(CN2S2)] and 2,5-[(S2N2C)OC4H2(CN)]

1992 ◽  
Vol 70 (3) ◽  
pp. 919-925 ◽  
Author(s):  
A. Wallace Cordes ◽  
Charles M. Chamchoumis ◽  
Robin G. Hicks ◽  
Richard T. Oakley ◽  
Kelly M. Young ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Crystal Structures ◽  
Monoclinic Space Group ◽  
Orthorhombic Space Group ◽  
Space Group ◽  
The Mean ◽  
Solid State Structures ◽  
Solid State Characterization

The preparation and solid state characterization of the bifunctional radical furan-2,5-bis(1,2,3,5-dithiadiazolyl) 2,5-[(S2N2C)OC4H2(CN2S2)] and the related monofunctional radical 2-cyanofuran-5-(1,2,3,5-dithiadiazolyl) 2,5-[(S2N2C)OC4H2(CN)] are described. The crystal structure of 2,5-[(S2N2C)OC4H2(CN2S2)] is orthorhombic, space group Pna21, and consists of interleaved arrays of dimers, for which the mean interannular [Formula: see text] contact is 3.137 Å. The crystal structure of the monofunctional radical 2,5-[(S2N2C)OC4H2(CN)] is monoclinic, space group P21/n, and consists of a ribbon-like network of dimers (mean interannular [Formula: see text] interconnected by close head-to-tail [Formula: see text] contacts. The dimer units form stacks parallel to z, with a mean interdimer [Formula: see text] separation of 3.956 Å. The similarities and differences between these two crystal structures and those of related benzene-substituted systems are discussed. Keywords: dithiadiazolyl radicals, furan-based diradicals, cyanofuran-based radicals, radical dimers, crystal structures.

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