Structural Studies of Histamine H1 Effector Molecules: The Crystal Structure of the Antihistamine Drug (+)-Chlorpheniramine Maleate; [(+)-S-1-(p-Chlorophenyl)-1-(2-pyridyl)-3-N,N-dimethylpropylamine maleate]

1974 ◽  
Vol 52 (10) ◽  
pp. 1872-1879 ◽  
Author(s):  
M. N. G. James ◽  
G. J. B. Williams
Keyword(s):  
Hydrogen Bond ◽  
Pyridyl Ring ◽  
Chlorpheniramine Maleate ◽  
Dimethylamino Group ◽  
Cell Dimensions ◽  
Antihistamine Drug ◽  
Intramolecular Hydrogen ◽  
Partially Occluded ◽  
Unit Cell Dimensions ◽  
Normal Formula

Dextrorotatory chlorpheniramine maleate crystallizes from warm ethyl acetate in a P21 cell containing two formula units of the salt, with unit cell dimensions; a = 5.7669(4) Å, b = 20.338(2) Å, c = 9.1347(8) Å, β = 103.73(2)°. Diffractometer data were collected with CuKα radiation to 2θ = 128°. The structure was solved and refined to R = 0.050 and wR = 0.066. The absolute configuration is confirmed as being S. The alkylamine chain is asymmetrically disposed to the two aryl rings, the p-chlorophenyl ring being more exposed and the 2-pyridyl ring partially occluded. The molecule has an open side to which both hydrogen bond and π orbital overlap linkages can occur. The maleate mono-anion is hydrogen bonded to the dimethylamino group via a normal [Formula: see text]linkage. The intramolecular hydrogen bond of the maleate ion is 2.444(5) Å long and is asymmetric.

Crystal structure of osimertinib mesylate Form B (Tagrisso), (C28H34N7O2)(CH3O3S)

2021 ◽  
pp. 1-9
Author(s):  
James A. Kaduk ◽  
Nicholas C. Boaz ◽  
Emma L. Markun ◽  
Amy M. Gindhart ◽  
Thomas N. Blanton
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Powder Diffraction ◽  
Density Functional ◽  
Amino Nitrogen ◽  
Strong Hydrogen Bond ◽  
Powder Diffraction File ◽  
Dimethylamino Group ◽  
Intramolecular Hydrogen

The crystal structure of osimertinib mesylate Form B has been solved and refined using synchrotron X-ray powder diffraction data and optimized using density functional techniques. Osimertinib mesylate Form B crystallizes in space group P-1 (#2) with a = 11.42912(17), b = 11.72274(24), c = 13.32213(22) Å, α = 69.0265(5), β = 74.5914(4), γ = 66.4007(4)°, V = 1511.557(12) Å3, and Z = 2. The crystal structure is characterized by alternating layers of cation–anion and parallel stacking interactions parallel to the ab-planes. The cation is protonated at the nitrogen atom of the dimethylamino group, which forms a strong hydrogen bond between the cation and the anion. That hydrogen atom also participates in a weaker intramolecular hydrogen bond to an amino nitrogen. There are two additional N–H⋅⋅⋅O hydrogen bonds between the cation and the anion. Several C–H⋅⋅⋅O hydrogen bonds also link the cations and anions. The powder pattern has been submitted to ICDD® for inclusion in the Powder Diffraction File™.

scholarly journals Synthesis, spectroscopic characterization, crystal structure and antifungal activity of thiourea derivatives containing a thiazole moiety

2010 ◽  
Vol 8 (3) ◽  
pp. 550-558 ◽  
Author(s):  
Sohail Saeed ◽  
Naghmana Rashid ◽  
Peter Jones ◽  
Rizwan Hussain ◽  
Moazzam Bhatti
Keyword(s):  
Crystal Structure ◽  
Antifungal Activity ◽  
Spectroscopic Characterization ◽  
Dilution Method ◽  
Monoclinic Space Group ◽  
Fragmentation Pattern ◽  
Thiourea Derivatives ◽  
Cell Dimensions ◽  
Intramolecular Hydrogen ◽  
Unit Cell Dimensions

AbstractFour novel thiourea derivatives containing a thiazole moiety were synthesized and characterized by IR, 1H and 13C NMR, mass spectrometry and elemental analysis. The crystal structure of 1a was determined from single crystal X-ray diffraction data. It crystallizes in monoclinic space group P21/n with unit cell dimensions a = 11.7752(6) Å, b= 3.8677(2) Å, c= 27.4126(13) Å and β = 92.734(5) Å. There is a strong intramolecular hydrogen bond of the type N-H⋯O, with H⋯O distance of 2.5869(19) Å. The mass fragmentation pattern has also been discussed. The antifungal activity of the synthesized compounds was studied by broth micro-dilution method and poisoned food technique. The compounds 1b and 1c possessed a broad spectrum of antifungal activity.

scholarly journals The crystal structure of 1-(4-chlorophenyl)-3-(4-methylbenzoyl)thiourea

2005 ◽  
Vol 3 (4) ◽  
pp. 780-791 ◽  
Author(s):  
Aamer Saeed ◽  
Masood Parvez
Keyword(s):  
Crystal Structure ◽  
Monoclinic Space Group ◽  
Fragmentation Pattern ◽  
X Ray Diffraction ◽  
1H And 13C Nmr ◽  
X Ray ◽  
Cell Dimensions ◽  
Intramolecular Hydrogen ◽  
Unit Cell Dimensions ◽  
Strong Intramolecular Hydrogen Bond

Abstract1-(4-Chlorophenyl)-3-(4-methylbenzoyl)thiourea was synthesized and characterized by IR,1H and 13C NMR, mass spectroscopy and the elemental analysis. The crystal structure was confirmed from single crystal X-ray diffraction data. It crystallizes in the monoclinic space group P21/c with unit cell dimensions a=12.038(3), b=6.330(6), c=18.912(5) Å and β=100.32(3)°. There is a strong intramolecular hydrogen bond of the type N−H...O, with distance N1...O1=2.659(3) Å. The structure is composed of dimers related by inversion centers. The dimers are formed by intermolecular interactions of the type N−H...S with N...S separation of 3.440(2) Å. The mass fragmentation pattern has also been discussed.

scholarly journals Isomorphous Crystals Formed by the Similar Supramolecular Motifs in Sorafenib Hydrochloride and Regorafenib Hydrochloride Salts

Crystals ◽  
2019 ◽  
Vol 9 (12) ◽  
pp. 649 ◽  
Author(s):  
Chi Uyen Phan ◽  
Jie Shen ◽  
Jiyong Liu ◽  
Jianming Mao ◽  
Xiurong Hu ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Crystal Structures ◽  
Pyridinium Cation ◽  
Supramolecular Motifs ◽  
Solubility Profile ◽  
Cell Dimensions ◽  
Unit Cell Dimensions ◽  
Similar Unit ◽  
Similar Crystal Structure

Sorafenib and regorafenib (or fluoro-sorafenib) are multikinase inhibitors active in the treatment of various human cancers, but their solubilities are very poor. To improve their solubilities, in this study, sorafenib hydrochloride (Sor·HCl, I) and regorafenib hydrochloride (Reg·HCl, II) have been prepared and their crystal structures were characterized. Their solubility properties in water were evaluated. Intriguingly, they are isomorphous crystal structures with the same space group and the similar unit cell dimensions, which were caused by the similar supramolecular patterns resulted by the formation of N–H···Cl− hydrogen bond instead of hydrogen bond between the protonated pyridinium cation and counterion. Moreover, the solubility properties displayed identical profiles. It may be concluded that a similar crystal structure leads to a comparable solubility profile.

4-Hydroxy-2-vinyl-2,3,4,5-tetrahydro-1-benzazepine and its 7-fluoro and 7-chloro analogues are isomorphous but not strictly isostructural

2009 ◽  
Vol 65 (3) ◽  
pp. o92-o96 ◽  
Author(s):  
Lina M. Acosta ◽  
Ali Bahsas ◽  
Alirio Palma ◽  
Justo Cobo ◽  
Michael B. Hursthouse ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Intermolecular Interactions ◽  
Unit Cell ◽  
Cell Dimensions ◽  
Sufficient Variation ◽  
Unit Cell Dimensions ◽  
Atomic Coordinates

4-Hydroxy-2-vinyl-2,3,4,5-tetrahydro-1-benzazepine, C12H15NO, (I), and its 7-fluoro and 7-chloro analogues, namely 7-fluoro-4-hydroxy-2-vinyl-2,3,4,5-tetrahydro-1-benzazepine, C12H14FNO, (II), and 7-chloro-4-hydroxy-2-vinyl-2,3,4,5-tetrahydro-1-benzazepine, C12H14ClNO, (III), are isomorphous, but with variations in the unit-cell dimensions which preclude in compound (III) one of the weaker intermolecular interactions found in compounds (I) and (II). Thus the compounds are not strictly isostructural in terms of the structurally significant intermolecular interactions, although the corresponding atomic coordinates are very similar. The azepine rings adopt chair conformations. The molecules are linked by a combination of N—H...O and O—H...N hydrogen bonds into chains of edge-fusedR33(10) rings, which in compounds (I) and (II) are further linked into sheets by a single C—H...π(arene) hydrogen bond. The significance of this study lies in its observation of isomorphism in compounds (I)–(III), and its observation of a sufficient variation in one of the cell dimensions effectively to alter the range of significant hydrogen bonds present in the crystal structures.

THE STRUCTURE OF AMINOPYRINE SALTS

1965 ◽  
Vol 43 (12) ◽  
pp. 3322-3329 ◽  
Author(s):  
Denys Cook
Keyword(s):  
Hydrogen Bond ◽  
Nitrogen Atom ◽  
Infrared Spectra ◽  
Dimethylamino Group ◽  
Complex Anions ◽  
Normal Formula

The infrared spectra of aminopyrine salts can be interpreted on the basis of protonation of the 4-dimethylamino group nitrogen atom. In the hydrohalides the normal [Formula: see text] hydrogen bond occurs, but in salts with complex anions an intramolecular [Formula: see text] hydrogen bond is probable, though an intermolecular one between the same partners cannot be ruled out.

The addition of 2,4-dinitrobenzenesulphenyl chloride to 2-methylenebicyclo[2.2.1]hept-5-ene: the crystal structure of 1-chloromethyl-3-endo-(2′,4′-dinitrophenylthio)tricyclo[2.2.1.02,6]heptane, C14H13ClN2O4S

1981 ◽  
Vol 59 (4) ◽  
pp. 658-662 ◽  
Author(s):  
Maria Przybylska ◽  
Dennis G. Garratt
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Double Bond ◽  
Structural Data ◽  
Sulphur Atom ◽  
Hydrogen Bond System ◽  
Cell Dimensions ◽  
Bond System ◽  
Bifurcated Hydrogen Bond ◽  
Unit Cell Dimensions

1-Chloromethyl-3-endo-(2′,4′-dinitrophenylthio)tricyclo[2.2.1.02,6]heptane, C14H13ClN2O4S, crystallizes in space group P21/a with unit cell dimensions a = 12.785(2), b = 10.653(1), c = 11.061(1) Å, β = 101.54(l)° Z = 4.The structure was solved from Patterson and Fourier maps. The parameters were refined by block-diagonal least-squares to a final R = 0.038 for 2063 observed reflections. The structural data provide unequivocal proof for our earlier ascertainment of configurational-specific exo attack upon the endocyclic double bond of 2-methylenebicyclo[2.2.1]hept-5-ene with homoallylic participation.The molecule is characterized by the presence of an interaction between oxygen of the 2-nitro group and a sulphur atom, and of a weak bifurcated hydrogen bond system involving [Formula: see text] bonds.

scholarly journals Influence of steric crowding on hydrogen bonding in anti-cancer quinols

2014 ◽  
Vol 70 (a1) ◽  
pp. C561-C561
Author(s):  
Carl Schwalbe ◽  
Geoffrey Wells ◽  
Malcolm Stevens
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Antitumor Activity ◽  
Donor Group ◽  
Anti Cancer ◽  
Cell Dimensions ◽  
Steric Crowding ◽  
Michael Acceptor ◽  
Classical Hydrogen Bond ◽  
Unit Cell Dimensions

The quinol 4-(1-benzenesulfonyl-1H-6-fluoroindol-2-yl)-4-hydroxycyclohexa-2,5-dienone (1) is strongly active against cancer cells [1]. Two "Michael acceptor" electrophilic β-carbons on the quinol ring are believed necessary for optimal antitumor activity, and disruption of thioredoxin signaling is a possible mechanism of action. As a model for the possible product, the adduct (2) with two molecules of ethanethiol was prepared. These molecules have just one classical hydrogen bond (HB) donor group, the quinol OH, but a surfeit of acceptors, namely one C=O and two SO2oxygen atoms (designated O15, O17 and O18) as well as O14, the OH itself. In (1) paired molecules form a R22(14) ring by O14-H...O17 HB with H...O distance 2.15 Å and O-H...O angle 156°. In (2) the two EtS groups on the same side of the quinol ring as O14 interfere with this motif. Instead, a C(7) chain is formed by less optimal O14-H...O17 HB (2.34 Å and 134°). In apparent compensation, an intramolecular C-H...O HB to O17 is shorter and straighter in (2). In both structures all O atoms accept C-H...O HB. The unit cell dimensions are dissimilar, but a motif persists: one phenyl CH and one indole CH group bite onto the same O atom, O15 in (1) but O18 in (2).

Hétérocycles à fonction quinone. V. Réaction anormale de la butanedione avec la diamino-1,2 anthraquinone; structure cristalline de la naphto [2,3-f] quinoxalinedione-7,12 obtenue

1984 ◽  
Vol 62 (3) ◽  
pp. 526-530 ◽  
Author(s):  
Michel Baron ◽  
Sylviane Giorgi-Renault ◽  
Jean Renault ◽  
Patrick Mailliet ◽  
Daniel Carré ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Direct Method ◽  
Intramolecular Hydrogen Bonding ◽  
Unit Cell ◽  
Principal Characteristic ◽  
X Ray Diffraction ◽  
X Ray ◽  
Cell Dimensions ◽  
Intramolecular Hydrogen ◽  
Unit Cell Dimensions

Butanedione reacts on heating with 1,2-diaminoanthraquinone to give, not the expected 2,3-dimethyl-naphtho[2,3-f]quinoxaline-7,12-dione 3, but 2-(2-hydroxy-2-methyl-3-oxobutyl)-3-methylnaphtho[2,3-f]quinoxaline-7,12-dione 4a whose structure was established by X-ray diffraction. This compound crystallizes in the triclinic [Formula: see text] space group with unit cell dimensions of a = 9.091 (1), b = 16.966 (4), c = 12.375 (3) Å; α = 100.75 (2), β = 101.83 (2), γ = 100.29 (2)°, V = 1789 Å3, Z = 4. The structure was resolved by the direct method and refined to R = 0.039 for 3027 independent reflections. The overall conformation of the molecule is essentially planar. The principal characteristic is the presence of two cyclic arrangements caused by intramolecular hydrogen bonding. 2,3-Dimethylnaphtho[2,3-f]quinoxaline-7,12-dione is the intermediate in this reaction.

The External Shape of Human γ GI Immunoglobulin from Crystal Sections

1971 ◽  
Vol 29 ◽  
pp. 428-429
Author(s):  
L. W. Labaw
Keyword(s):  
Molecular Weight ◽  
Sodium Phosphate ◽  
Osmium Tetroxide ◽  
Unit Cell ◽  
Monoclinic Space Group ◽  
X Ray ◽  
Large Molecular Weight ◽  
Cell Dimensions ◽  
Unit Cell Dimensions ◽  
Crystallographic Axes

Crystals of a human γGl immunoglobulin have the external morphology of diamond shaped prisms. X-ray studies have shown them to be monoclinic, space group C2, with 2 molecules per unit cell. The unit cell dimensions are a = 194.1, b = 91.7, c = 51.6Å, 8 = 102°. The relatively large molecular weight of 151,000 and these unit cell dimensions made this a promising crystal to study in the EM.Crystals similar to those used in the x-ray studies were fixed at 5°C for three weeks in a solution of mother liquor containing 5 x 10-5M sodium phosphate, pH 7.0, and 0.03% glutaraldehyde. They were postfixed with 1% osmium tetroxide for 15 min. and embedded in Maraglas the usual way. Sections were cut perpendicular to the three crystallographic axes. Such a section cut with its plane perpendicular to the z direction is shown in Fig. 1.This projection of the crystal in the z direction shows periodicities in at least four different directions but these are only seen clearly by sighting obliquely along the micrograph.

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