Synthon preference in a hydrated β-resorcylic acid structure and its cocrystal with thymine

2015 ◽  
Vol 71 (12) ◽  
pp. 1042-1047 ◽  
Author(s):  
Balasubramanian Sridhar
Keyword(s):  
Carboxylic Acid ◽  
Water Molecule ◽  
Functional Groups ◽  
Acid Molecule ◽  
Asymmetric Unit ◽  
Space Group ◽  
Water Solvent ◽  
Donor And Acceptor ◽  
Acid Acid ◽  
Hydrogen Bonded

Multicomponent crystals or cocrystals play a significant role in crystal engineering, the main objective of which is to understand the role of intermolecular interactions and to utilize such understanding in the design of novel crystal structures. Molecules possessing carboxylic acid and amide functional groups are good candidates for forming cocrystals. β-Resorcylic acid monohydrate, C7H6O4·H2O, (I), crystallizes in the triclinic space groupP-1 with one β-resorcylic acid molecule and one water molecule in the asymmetric unit. The cocrystal thymine–β-resorcylic acid–water (1/1/1), C5H6N2O2·C7H6O4·H2O, (II), crystallizes in the orthorhombic space groupPca21, with one molecule each of thymine, β-resorcylic acid and water in the asymmetric unit. All available donor and acceptor atoms in (I) and (II) are utilized for hydrogen bonding. The acid and amide functional groups are well known for the formation of self-complementary acid–acid and amide–amide homosynthons. In (I), an acid–acid homosynthon is observed, while in (II), an amide–acid heterosynthon is present. In (I), the β-resorcylic acid molecule exhibits the expected intramolecularS(6) motif between the hydroxy and carbonyl O atoms, and an intermolecularR22(8) dimer motif between the carboxylic acid groups; only the former motif is observed in (II). The water solvent molecule in (I) propagates the discrete dimers into two-dimensional hydrogen-bonded sheets. In (II), thymine and β-resorcylic acid molecules do not form self-complementary amide–amide and acid–acid homosynthons; instead, a thymine–β-resorcylic acid heterosynthon is observed. With the help of the water molecule, this heterosynthon is aggregated into a three-dimensional hydrogen-bonded network. The absence of thymine base pairing in (II) might be linked to the availability of additional functional groups and the preference of the donor and acceptor hydrogen-bond combinations.

Novel and Disparate Hydrogen-Bonding Associations in 13-Amino-6-hydroxy-13-methyl-1,4,8,11-tetraazacyclotetradecane Tetrahydrochloride Monohydrate

2005 ◽  
Vol 58 (1) ◽  
pp. 60 ◽  
Author(s):  
Jack M. Harrowfield ◽  
Yang Kim ◽  
Young Hoon Lee ◽  
Gareth L. Nealon ◽  
Brian W. Skelton ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Water Molecule ◽  
Title Compound ◽  
Monoclinic Space Group ◽  
Asymmetric Unit ◽  
Space Group ◽  
Cation Sites ◽  
L 13 ◽  
Hydrogen Bonded

The title compound crystallizes in the monoclinic space group Pn with two independent [LH4]Cl4·H2O formula units (L = 13-amino-6-hydroxy-13-methyl-1,4,8,11-tetraazacyclotetradecane) in the asymmetric unit. Despite pseudo-symmetry, these two units exhibit subtle and interesting differences in their hydrogen-bonded association by the interchange of the water molecule site with one of the chloride anions. Although a pentamine, L crystallizes as a tetrahydrochloride in which the tetracation has a conformation similar to that of tetraprotonated cyclam (1,4,8,11-tetraazacyclotetradecane), despite a different pattern of protonation sites. Difficulties in purification are perpetuated in the crystal, the minor isomeric component co-crystallizing in one of the cation sites.

scholarly journals Crystal structures of 1′-aminocobaltocenium-1-carboxylic acid chloride monohydrate and of its azo dye 1′-[2-(1-amino-2,6-dimethylphenyl)diazen-1-yl]cobaltocenium-1-carboxylic acid hexafluoridophosphate monohydrate

2019 ◽  
Vol 75 (2) ◽  
pp. 208-213 ◽  
Author(s):  
Markus Jochriem ◽  
Klaus Wurst ◽  
Holger Kopacka ◽  
Benno Bildstein
Keyword(s):  
Carboxylic Acid ◽  
Water Molecule ◽  
Functional Groups ◽  
Acid Chloride ◽  
Supramolecular Network ◽  
Carboxylic Acid Chloride ◽  
Positional Disorder ◽  
Counter Ion ◽  
Chloride Monohydrate ◽  
Hydrogen Bonded

1′-Aminocobaltocenium-1-carboxylic acid chloride, [Co(C5H6N)(C6H5O2)]Cl·H2O, (3), and its azo derivative 1′-[2-(1-amino-2,6-dimethylphenyl)diazen-1-yl]cobaltocenium-1-carboxylic acid hexafluoridophosphate, [Co(C13H14N3)(C6H5O2)]PF6·H2O (5) were obtained from cobaltocenium-1,1′-dicarboxylic acid hexafluoridophosphate by converting one carboxyl group to its chlorocarboxyl derivative followed by chloride/azide exchange, Curtius rearrangement, diazotiation and azo coupling with 2,6-dimethylaniline. Both title compounds crystallize as their monohydrates. In the crystal structure of 3, both functional groups lie in the same direction, with the Cp rings being nearly eclipsed, and participate in an extended hydrogen-bonded supramolecular network including the counter-ion and the water molecule of crystallization. Although the functional groups in 5 are somewhat further apart, bearing a greater torsion angle with the Cp rings now staggered, a similar supramolecular network is observed with not only the carboxylic acid and azo groups, but also with the more remote amino group participating in a hydrogen-bonded network, again including the counter-ion and the water molecule. The hexafluoridophosphate ion shows positional disorder. Compound 3 was refined as an inversion twin. In 5, each of the six F atoms is disordered over two sets of sites in a 1:1 ratio.

scholarly journals Crystal structures of four co-crystals of (E)-1,2-di(pyridin-4-yl)ethene with 4-alkoxybenzoic acids: 4-methoxybenzoic acid–(E)-1,2-di(pyridin-4-yl)ethene (2/1), 4-ethoxybenzoic acid–(E)-1,2-di(pyridin-4-yl)ethene (2/1), 4-n-propoxybenzoic acid–(E)-1,2-di(pyridin-4-yl)ethene (2/1) and 4-n-butoxybenzoic acid–(E)-1,2-di(pyridin-4-yl)ethene (2/1)

2016 ◽  
Vol 72 (11) ◽  
pp. 1666-1671 ◽  
Author(s):  
Yohei Tabuchi ◽  
Kazuma Gotoh ◽  
Hiroyuki Ishida
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Acid Molecule ◽  
Asymmetric Unit ◽  
Space Group ◽  
Π Interactions ◽  
Column Structure ◽  
Acid And Base ◽  
Methoxybenzoic Acid ◽  
Hydrogen Bonded

The crystal structures of four hydrogen-bonded co-crystals of 4-alkoxybenzoic acid–(E)-1,2-di(pyridin-4-yl)ethene (2/1), namely, 2C8H8O3·C12H10N2, (I), 2C9H10O3·C12H10N2, (II), 2C10H12O3·C12H10N2, (III) and 2C11H14O3·C12H10N2, (IV), have been determined at 93 K. In compounds (I) and (IV), the asymmetric units are each composed of one 4-alkoxybenzoic acid molecule and one half-molecule of (E)-1,2-di(pyridin-4-yl)ethene, which lies on an inversion centre. The asymmetric unit of (II) consists of two crystallographically independent 4-ethoxybenzoic acid molecules and one 1,2-di(pyridin-4-yl)ethene molecule. Compound (III) crystallizes in a non-centrosymmetric space group (Pc) and the asymmetric unit comprises four 4-n-propoxybenzoic acid molecules and two (E)-1,2-di(pyridin-4-yl)ethane molecules. In each crystal, the acid and base components are linked by O—H...N hydrogen bonds, forming a linear hydrogen-bonded 2:1 unit of the acid and the base. In (I), (II) and (III), intermolecular C—H...O interactions are observed. The 2:1 units of (I) and (II) are linkedviaC—H...O hydrogen bonds, forming tape structures. In (III), the C—H...O hydrogen bonds, except for those formed in the units, link the two crystallographically independent 2:1 units. In (IV), no C—H...O interactions are observed, but π–π and C—H...π interactions link the units into a column structure.

scholarly journals Crystal structure of poly[diaqua(μ-2-carboxyacetato-κ3O,O′:O′′)(2-carboxyacetato-κO)di-μ-chlorido-dicobalt(II)]

2016 ◽  
Vol 72 (1) ◽  
pp. 21-24
Author(s):  
Yasmina Bouaoud ◽  
Zouaoui Setifi ◽  
Andrii Buvailo ◽  
Vadim A. Potaskalov ◽  
Hocine Merazig ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Carboxylic Acid ◽  
Coordination Polymer ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Two Dimensional ◽  
Acid Molecule ◽  
Carbonyl Groups ◽  
Asymmetric Unit ◽  
Dinuclear Unit

The asymmetric unit of the title polymer, [Co2(C3H3O4)2Cl2(H2O)2]n, comprises one CoIIatom, one water molecule, one singly deprotonated malonic acid molecule (HMal−; systematic name 2-carboxyacetate) and one Cl−anion. The CoIIatom is octahedrally coordinated by the O atom of a water molecule, by one terminally bound carboxylate O atom of an HMal−anion and by two O atoms of a chelating HMal−anion, as well as by two Cl−anions. The Cl−anions bridge two CoIIatoms, forming a centrosymmetric Co2Cl2core. Each malonate ligand is involved in the formation of six-membered chelate rings involving one CoIIatom of the dinuclear unit and at the same time is coordinating to another CoIIatom of a neighbouring dinuclear unit in a bridging mode. The combination of chelating and bridging coordination modes leads to the formation of a two-dimensional coordination polymer extending parallel to (001). Within a layer, O—Hwater...Cl and O—Hwater...O hydrogen bonds are present. Adjacent layers are linked through O—H...O=C hydrogen bonds involving the carboxylic acid OH and carbonyl groups.

Aripiprazole salts. III. Bis(aripiprazolium) oxalate–oxalic acid (1/1)

2013 ◽  
Vol 69 (2) ◽  
pp. 186-190 ◽  
Author(s):  
Eleonora Freire ◽  
Griselda Polla ◽  
Ricardo Baggio
Keyword(s):  
Hydrogen Bonds ◽  
Oxalic Acid ◽  
Intermolecular Interaction ◽  
Three Dimensional ◽  
Acid Molecule ◽  
Asymmetric Unit ◽  
Space Group ◽  
Dimensional Network ◽  
Centrosymmetric Dimers ◽  
Hydrogen Bonded

The asymmetric unit of the title salt [systematic name: bis(4-(2,3-dichlorophenyl)-1-{4-[(2-oxo-1,2,3,4-tetrahydroquinolin-7-yl)oxy]butyl}piperazin-1-ium) oxalate–oxalic acid (1/1)], 2C23H28Cl2N3O2+·C2O42−·C2H2O4, consists of one protonated aripiprazole unit (HArip+), half an oxalate dianion and half an oxalic acid molecule, the latter two lying on inversion centres. The conformation of the HArip+cation differs from that in other reported salts and resembles more the conformation of neutral Arip units in reported polymorphs and solvates. The intermolecular interaction linking HArip+cations is also similar to those in reported Arip compounds crystallizing in the space groupP\overline{1}, with head-to-head N—H...O hydrogen bonds generating centrosymmetric dimers, which are further organized into planar ribbons parallel to (01\overline{2}). The oxalate anions and oxalic acid molecules form hydrogen-bonded chains running along [010], which `pierce' the planar ribbons, interacting with them through a number of stronger N—H...O and weaker C—H...O hydrogen bonds, forming a three-dimensional network.

scholarly journals Diosgenin hemihydrate

2012 ◽  
Vol 68 (8) ◽  
pp. o2357-o2357 ◽  
Author(s):  
María-Guadalupe Hernández Linares ◽  
Sylvain Bernès ◽  
Marcos Flores-Alamo ◽  
Gabriel Guerrero-Luna ◽  
Anselmo A. Martínez-Gallegos
Keyword(s):  
Crystal Structure ◽  
Water Molecule ◽  
Dimethyl Sulfoxide ◽  
Starting Material ◽  
Water Molecules ◽  
Asymmetric Unit ◽  
Acta Cryst ◽  
X Ray ◽  
Hydroxy Groups ◽  
Hydrogen Bonded

Diosgenin [or (22R,25R)-spirost-5-en-3β-ol] is the starting material of the Marker degradation, a cheap semi-synthesis of progesterone, which has been designated as an International Historic Chemical Landmark. Thus far, a single X-ray structure for diosgenin is known, namely its dimethyl sulfoxide solvate [Zhanget al.(2005).Acta Cryst.E61, o2324–o2325]. We have now determined the structure of the hemihydrate, C27H42O3·0.5H2O. The asymmetric unit contains two diosgenin molecules, with quite similar conformations, and one water molecule. Hydroxy groups in steroids and water molecules form O—H...O hydrogen-bondedR54(10) ring motifs. Fused edge-sharingR(10) rings form a backbone oriented along [100], which aggregates the diosgenin molecules in the crystal structure.

scholarly journals Crystal structures of hydrogen-bonded co-crystals as liquid crystal precursors: 4-(n-pentyloxy)benzoic acid–(E)-1,2-bis(pyridin-4-yl)ethene (2/1) and 4-(n-hexyloxy)benzoic acid–(E)-1,2-bis(pyridin-4-yl)ethene (2/1)

2016 ◽  
Vol 72 (12) ◽  
pp. 1771-1775
Author(s):  
Yohei Tabuchi ◽  
Kazuma Gotoh ◽  
Hiroyuki Ishida
Keyword(s):  
Liquid Crystal ◽  
Hydrogen Bonds ◽  
Benzoic Acid ◽  
Crystal Structures ◽  
Acid Molecule ◽  
Asymmetric Unit ◽  
Average Structure ◽  
Π Interactions ◽  
Acid And Base ◽  
Hydrogen Bonded

The crystal structures of title hydrogen-bonded co-crystals, 2C12H16O3·C12H10N2, (I), and 2C13H18O3·C12H10N2, (II), have been determined at 93 K. In (I), the asymmetric unit consists of one 4-(n-pentyloxy)benzoic acid molecule and one half-molecule of (E)-1,2-bis(pyridin-4-yl)ethene, which lies about an inversion centre. The asymmetric unit of (II) comprises two crystallographically independent 4-(n-hexyloxy)benzoic acid molecules and one 1,2-bis(pyridin-4-yl)ethene molecule. In each crystal, the acid and base components are linked by O—H...N hydrogen bonds, forming a linear hydrogen-bonded 2:1 unit of the acid and the base. The 2:1 units are linkedviaC—H...π and π–π interactions [centroid–centroid distances of 3.661 (2) and 3.909 (2) Å for (I), and 3.546 (2)–3.725 (4) Å for (II)], forming column structures. In (II), the base molecule is orientationally disordered over two sets of sites approximately around the N...N molecular axis, with an occupancy ratio of 0.647 (4):0.353 (4), and the average structure of the 2:1 unit adopts nearly pseudo-C2symmetry. Both compounds show liquid-crystal behaviour.

A new polymorph of bis(2-aminopyridinium) fumarate–fumaric acid (1/1) from powder X-ray diffraction

2013 ◽  
Vol 69 (8) ◽  
pp. 896-900 ◽  
Author(s):  
Shuichao Dong ◽  
Yaqiu Tao ◽  
Xiaodong Shen ◽  
Zhigang Pan
Keyword(s):  
Hydrogen Bonds ◽  
Fumaric Acid ◽  
Diffraction Method ◽  
Monoclinic Space Group ◽  
Asymmetric Unit ◽  
X Ray Diffraction ◽  
Acta Cryst ◽  
Space Group ◽  
X Ray ◽  
Hydrogen Bonded

A new polymorph of bis(2-aminopyridinium) fumarate–fumaric acid (1/1), 2C5H7N2+·C4H2O42−·C4H4O4, was obtained and its crystal structure determined by powder X-ray diffraction. The new polymorph (form II) crystallizes in the triclinic system (space groupP\overline{1}), while the previous reported polymorph [form I; Ballabh, Trivedi, Dastidar & Suresh (2002).CrystEngComm,4, 135–142; Büyükgüngör, Odabaşoğlu, Albayrak & Lönnecke (2004).Acta Cryst.C60, o470–o472] is monoclinic (space groupP21/c). In both forms I and II, the asymmetric unit consists of one 2-aminopyridinium cation, half a fumaric acid molecule and half a fumarate dianion. The fumarate dianion is involved in hydrogen bonding with two neighbouring 2-aminopyridinium cations to form a hydrogen-bonded trimer in both forms. In form II, the hydrogen-bonded trimers are interlinked across centres of inversionviapairs of N—H...O hydrogen bonds, whereas such trimers are joinedviasingle N—H...O hydrogen bonds in form I, leading to different packing modes for forms I and II. The results demonstrate the relevance and application of the powder diffraction method in the study of polymorphism of organic molecular materials.

Pseudosymmetry in a cyclopalladated compound

2012 ◽  
Vol 68 (8) ◽  
pp. m223-m225 ◽  
Author(s):  
William Raven ◽  
Irmgard Kalf ◽  
Ulli Englert
Keyword(s):  
Title Complex ◽  
Unit Cell ◽  
Inversion Symmetry ◽  
Asymmetric Unit ◽  
Enantiomerically Pure ◽  
Space Group ◽  
Hydrogen Bonded

The enantiomerically pure title complex, [SP-4-4]-(R)-[2-(1-aminoethyl)phenyl-κ2C1,N]chlorido(quinoline-κN)palladium(II) acetone hemisolvate, [Pd(C8H10N)Cl(C9H7N)]·0.5C3H6O, crystallizes with four molecules of the organopalladium complex and two molecules of acetone in the asymmetric unit. This corresponds to a discrete hydrogen-bonded aggregate and to the content of the unit cell in the space groupP1. Pronounced pseudo-inversion symmetry relates pairs of these objects in the asymmetric unit.

scholarly journals Crystal structures of three co-crystals of 1,2-bis(pyridin-4-yl)ethane with 4-alkoxybenzoic acids: 4-ethoxybenzoic acid–1,2-bis(pyridin-4-yl)ethane (2/1), 4-n-propoxybenzoic acid–1,2-bis(pyridin-4-yl)ethane (2/1) and 4-n-butoxybenzoic acid–1,2-bis(pyridin-4-yl)ethane (2/1)

2015 ◽  
Vol 71 (11) ◽  
pp. 1340-1344 ◽  
Author(s):  
Yohei Tabuchi ◽  
Kazuma Gotoh ◽  
Hiroyuki Ishida
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Inversion Symmetry ◽  
Acid Molecule ◽  
Asymmetric Unit ◽  
Ethane Molecule ◽  
Hydrogen Bonded

The crystal structures of three hydrogen-bonded co-crystals of 4-alkoxybenzoic acid–1,2-bis(pyridin-4-yl)ethane (2/1), namely, 2C9H10O3·C12H12N2, (I), 2C10H12O3·C12H12N2, (II), and 2C11H14O3·C12H12N2, (III), have been determined at 93, 290 and 93 K, respectively. In (I), the asymmetric unit consists of one 4-ethoxybenzoic acid molecule and one half-molecule of 1,2-bis(pyridin-4-yl)ethane, which lies on an inversion centre. In (II) and (III), the asymmetric units each comprise two crystallographically independent 4-alkoxybenzoic acid molecules and one 1,2-bis(pyridin-4-yl)ethane molecule. In each crystal, the two components are linked by O—H...N hydrogen bonds, forming a linear hydrogen-bonded 2:1unit of the acid and the base. Similar to the structure of 2:1 unit of (I), the units of (II) and (III) adopt nearly pseudo-inversion symmetry. The 2:1 units of (I), (II) and (III) are linkedviaC—H...O hydrogen bonds, forming tape structures.

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