Molecular Cocrystals of Aromatic Carboxylic Acids with 1,1-Diethylurea: Synthesis and the Crystal Structures of a Series of Nitro-Substituted Analogues

2000 ◽  
Vol 53 (3) ◽  
pp. 203 ◽  
Author(s):  
Graham Smith ◽  
Michael G. Coyne ◽  
Jonathan M. White
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acids ◽  
Acid Group ◽  
X Ray Diffraction ◽  
Chain Polymer ◽  
Aromatic Carboxylic Acids ◽  
Nitrobenzoic Acid ◽  
Simple Chain ◽  
A Chain ◽  
Polymeric Structures

Molecular adducts of 1,1-diethylurea with the nitro-substituted aromatic carboxylic acids 2-nitrobenzoic acid, [(C7H5NO4)(C5H12N2O)] (1), 3-nitrobenzoic acid, [(C7H5NO4)(C5H12N2O)] (2), 4-nitrobenzoic acid, [(C7H5NO4)2(C5H12N2O)] (3), 3,5-dinitrobenzoic acid, [(C7H4N2O6)(C5H12N2O)] (4), 5-nitrosalicylic acid, [(C7H5NO5)(C5H12N2O)] (5) and 3,5-dinitrosalicylic acid, [(C7H4N2O7)(C5H12N2O)] (6), have been prepared and characterized by using infrared spectroscopy, and, in the case of four of these [(1), (4), (5) and (6)], by single-crystal X-ray diffraction methods. In all examples, primary cyclic hydrogen-bonding interactions are found between the amide group of the substituted urea and the carboxylic acid group of the acid, while further peripheral associations result predominantly in simple chain polymeric structures, and in one case [adduct (1)], a cyclic tetramer. The crystal structure of the parent 1,1-diethylurea has also been determined, revealing a cyclic hydrogen-bonded tetramer which forms into a chain polymer by weak hydrogen-bonding associations.

Molecular Cocrystals of Aromatic Carboxylic Acids with Unsymmetrically Substituted Ureas. The Structures of Phenylurea and the 1 : 1 Adducts of Phenylurea with a Series of Nitro-Substituted Acids

2000 ◽  
Vol 53 (9) ◽  
pp. 767 ◽  
Author(s):  
Raymond C. Bott ◽  
Graham Smith ◽  
Urs D. Wermuth ◽  
Nathan C. Dwyer
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Oxygen Atom ◽  
X Ray Diffraction ◽  
Chain Polymer ◽  
Nitrobenzoic Acid ◽  
Hydrogen Bonding Interactions ◽  
Simple Chain ◽  
A Chain ◽  
Polymeric Structures

The crystal structure of phenylurea (1), [(C7H8N2O)], has been determined and revealed a simple cyclic dimer involving hydrogen bonding between the two nitrogen atoms of one molecule and the oxygen atom of a second molecule. The system is completed by a hydrogen bond between the non-substituted nitrogen atom of a third molecule and the oxygen atom of the second molecule to form a chain polymer. The 1 : 1 molecular adducts of phenylurea with 2-nitrobenzoic acid, [(C7H5NO4)(C7H8N2O)] (2), 3-nitrobenzoic acid, [(C7H5NO4)(C7H8N2O)] (3), 3,5-dinitrobenzoic acid, [(C7H4N2O6)(C7H8N2O)] (4), 2,4,6-trinitrobenzoic acid, [(C7H3N3O8)(C7H8N2O)] (5), 5-nitrosalicylic acid, [(C7H5NO5)(C7H8N2O)] (6), and 3,5-dinitrosalicylic acid, [(C7H4N2O7)(C7H8N2O)] (7) have been prepared and characterized by infrared spectroscopy and, for compounds (2), (4), (5) and (6), by single crystal X-ray diffraction methods. The adduct involving phenylurea and 4-nitrobenzoic acid could not be isolated from this system. In all examples, cyclic hydrogen-bonding interactions are found between the phenylurea and the carboxylic acid groups. All display further peripheral hydrogen bond associations that result in the formation of predominantly simple chain polymeric structures.

Molecular Adducts of 2,6-Diaminopyridine with Nitro-Substituted Aromatic Carboxylic Acids and the Crystal Structure of the 1 : 1 Adduct of 2,6-Diaminopyridine with 2-Nitrobenzoic Acid

1999 ◽  
Vol 52 (1) ◽  
pp. 71 ◽  
Author(s):  
Graham Smith ◽  
Catherine E. Pascoe ◽  
Colin H. L. Kennard ◽  
Karl A. Byriel
Keyword(s):  
Crystal Structure ◽  
Proton Transfer ◽  
Carboxylic Acids ◽  
Monoclinic Space Group ◽  
Chain Polymer ◽  
Aromatic Carboxylic Acids ◽  
X Ray Crystallography ◽  
Nitrobenzoic Acid ◽  
A Cell ◽  
A Chain

The 1 : 1 adducts of 2,6-diaminopyridine (2,6-dap) with a series of nitro-substituted aromatic carboxylic acids have been prepared and the crystal structure of one of these, with 2-nitrobenzoic acid (2-nba), [(2,6-dap)+ (2-nba)-] has been determined by X-ray crystallography and refined to a residual R 0·034 for 655 observed reflections. Crystals are monoclinic, space group P 21/c, with four molecules in a cell of dimensions a 7·376(2), b 22·837(3), c 7·716(2) Å, β 90·01(2)°. The structure involves proton transfer with the resulting pyridinium proton and an amine proton combining with the carboxyl oxygens of the 2-nba molecule in a primary cyclic hydrogen-bonding association. Additional interactions, involving all the remaining amine protons of 2,6-dap with both carboxyl oxygens and one nitro oxygen of 2-nba, complete a chain polymer structure. All other members of this series have been confirmed by infrared spectroscopy as proton transfer adducts.

Molecular Cocrystals of Carboxylic Acids. XXV The Utility of Urea in Structure Making with Carboxylic Acids and the Crystal Structures of a Set of Six Adducts with Aromatic Acids

1997 ◽  
Vol 50 (7) ◽  
pp. 727 ◽  
Author(s):  
Graham Smith ◽  
Katherine E. Baldry ◽  
Karl A. Byriel ◽  
Colin H. L. Kennard
Keyword(s):  
Hydrogen Bonding ◽  
Infrared Spectroscopy ◽  
Dicarboxylic Acid ◽  
Carboxylic Acids ◽  
Phthalic Acid ◽  
Aromatic Acids ◽  
Aminobenzoic Acid ◽  
X Ray Diffraction ◽  
X Ray ◽  
Polymeric Structures

Molecular adducts of urea with six aromatic carboxylic acids have been prepared and characterized by using X-ray diffraction methods and infrared spectroscopy. These compounds are with 5-nitrosalicylic acid [(C7H5NO5)2(CH4N2O)] (1), 3,5-dinitrosalicylic acid [(C7H4N2O7)(CH4N2O)] (2), 4-aminobenzoic acid [(C7H7NO2)2(CH4N2O)] (3), o-phthalic acid [(C8H6O4)(CH4N2O)] (4), pyrazine-2,3-dicarboxylic acid [(C4H4N2O4)(CH4N2O)] (5) and pyridine-2,6-dicarboxylic acid [(C7H5NO4)(CH4N2O)2] (6). In the majority of the adducts, all six potential interactive sites on the urea molecules are utilized in hydrogen bonding, giving polymeric structures.

The Crystal and Molecular Structure of the 1:1 Adduct Hydrate of Pyrazine-2,3-dicarboxylic Acid with 1,1-Diethylurea

2000 ◽  
Vol 53 (12) ◽  
pp. 999 ◽  
Author(s):  
Graham Smith ◽  
Colin H. L. Kennard
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Dicarboxylic Acid ◽  
Lattice Water Molecule ◽  
Crystal And Molecular Structure ◽  
Acid Group ◽  
X Ray Diffraction ◽  
Carboxylic Acid Group ◽  
X Ray ◽  
Bonding Interaction

The adduct hydrate of 1,1-diethylurea with pyrazine-2,3-dicarboxylic acid, [(C6H4N2O4)(C5H12N2O)].H2O has been prepared and characterized using low-temperature single-crystal X-ray diffraction methods. A primary asymmetric cyclic hydrogen-bonding interaction, similar to those found in other adducts of 1,1-diethylurea with the nitro-substituted aromatic acids, was found between the amide group of the substituted urea and one carboxylic acid group of the acid. Further peripheral hydrogen-bonding associations involving both the f irst and the second carboxylic acid groups, urea and the lattice water molecule result in a ribbon polymer structure.

The Crystal Structure of Acifluorfen {5-[2-Chloro-4-(trifluoromethyl)-phenoxy]-2-nitrobenzoic Acid}

1987 ◽  
Vol 40 (6) ◽  
pp. 1131 ◽  
Author(s):  
CHL Kennard ◽  
G Smith ◽  
T Hari
Keyword(s):  
Crystal Structure ◽  
Carboxylic Acid ◽  
Phenyl Ring ◽  
Acid Group ◽  
Monoclinic Space Group ◽  
X Ray Diffraction ◽  
Carboxylic Acid Group ◽  
X Ray ◽  
Nitrobenzoic Acid ◽  
Cell Dimensions

The crystal structure of the herbicide acifluorfen (5-[(2-chloro-4-trifluoromethyl)]phenoxy-2- nitrobenzoic acid] has been determined by X-ray diffraction and refined to a residual of 0.051for 1124 observed reflections. Crystals are monoclinic, space group C2/c with cell dimensions a 26.848(7), b 8 .O29(2), c 19 .Ol4(6) �, ,R l34.72(2)� and Z 8. The molecules form centrosymmetric hydrogen-bonded cyclic dimers [O---0, 2.637(7) �] with the carboxylic acid group and the phenoxy group synclinally related to the first phenyl ring while the nitro substituent isessentially coplanar with the ring.

Inhibitors of the geotropic response in plants. The crystal structures of 2-[(Naphthalen-2-yl)carbamoyl]benzoic acid (β-Naptalam), 2-(Phenylcarbamoyl)-benzoic acid and 2-(5-Phenyl-1,3,4-oxadiazol-2-yl)benzoic acid

1983 ◽  
Vol 36 (12) ◽  
pp. 2455 ◽  
Author(s):  
G Smith ◽  
CHL Kennard ◽  
GF Katekar
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Benzoic Acid ◽  
Crystal Structures ◽  
Carboxylic Acids ◽  
Intermolecular Hydrogen Bonding ◽  
X Ray Diffraction ◽  
X Ray ◽  
Carboxylic Acid Groups ◽  
Phthalamic Acid

The crystal structures of three geotropically active phthalamic acid derivatives have been determined by means of X-ray diffraction and the structural systematics for the series compared. The three acids are conformationally similar and, in contrast to the tendency among carboxylic acids to form hydrogen-bonded dimers, they exist as monomers with intermolecular hydrogen bonding between the carboxylic acid groups and the nitrogen or oxygen of the amide side chains.

scholarly journals Coordination polymeric structures in the sodium salt of 4-chloro-3-nitrobenzoic acid and the sodium and potassium salts of 4-nitroanthranilic acid

2013 ◽  
Vol 69 (12) ◽  
pp. 1472-1477 ◽  
Author(s):  
Graham Smith
Keyword(s):  
Hydrogen Bonding ◽  
Water Molecule ◽  
Coordination Polyhedron ◽  
Three Dimensional ◽  
Dimensional Structure ◽  
Two Dimensional ◽  
Π Interactions ◽  
Nitrobenzoic Acid ◽  
Distorted Octahedral ◽  
Polymeric Structures

The structures of the hydrated sodium salts of 4-chloro-3-nitrobenzoic acid {poly[aqua(μ4-4-chloro-3-nitrobenzoato)sodium(I)], [Na(C7H3ClNO4)(H2O)]n, (I)} and 2-amino-4-nitrobenzoic acid {poly[μ-aqua-aqua(μ3-2-amino-4-nitrobenzoato)sodium(I)], [Na(C7H5N2O4)(H2O)2]n, (II)}, and the hydrated potassium salt of 2-amino-4-nitrobenzoic acid {poly[μ-aqua-aqua(μ5-2-amino-4-nitrobenzoato)potassium(I)], [K(C7H5N2O4)(H2O)]n, (III)} have been determined and their complex polymeric structures described. All three structures are stabilized by intra- and intermolecular hydrogen bonding and strong π–π ring interactions. In the structure of (I), the distorted trigonal bipyrimidal NaO5coordination polyhedron comprises a monodentate water molecule and four bridging carboxylate O-atom donors, generating a two-dimensional polymeric structure lying parallel to (001). Intra-layer hydrogen-bonding associations and strong inter-ring π–π interactions are present. Structure (II) has a distorted octahedral NaO6stereochemistry, with four bridging O-atom donors, two from a single carboxylate group and two from a single nitro group and three from the two water molecules, one of which is bridging. Na centres are linked through centrosymmetric four-membered duplex water bridges and through 18-membered duplex head-to-tail ligand bridges. Similar centrosymmetric bridges are found in the structure of (III), and in both (II) and (III) strong inter-ring π–π interactions are found. A two-dimensional layered structure lying parallel to (010) is generated in (II), whereas in (III) the structure is three-dimensional. With (III), the irregular KO7coordination polyhedron comprises a doubly bridging water molecule, a single bidentate bridging carboxylate O-atom donor and three bridging O-atom donors from the two nitro groups. A three-dimensional structure is generated. These coordination polymer structures are among the few examples of metal complexes of any type with either 4-chloro-3-nitrobenzoic acid or 4-nitroanthranilic acid.

Temperature-controlled formation of Anderson-type compounds and their conversion to [γ-Mo8O26]4−-based variants using pendent ligands

2017 ◽  
Vol 72 (9) ◽  
pp. 655-664 ◽  
Author(s):  
Ai-xiang Tian ◽  
Ting-ting Li ◽  
Yan Tian ◽  
Huai-ping Ni ◽  
Xue-bin Ji ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Organic Ligands ◽  
Zigzag Chain ◽  
X Ray Diffraction ◽  
X Ray ◽  
Hydrogen Bonding Interactions ◽  
Elemental Analyses ◽  
Nuclear Clusters ◽  
Temperature Controlled ◽  
A Chain

AbstractBy tuning the reaction temperature, two Anderson- and two [γ-Mo8O26]4−-based compounds decorated by pendent organic ligands, [CuII9(bpz)2(pz)2(H2O)24][H2(Cr(OH)5Mo6O19)4]·11H2O (1), [CuII(bpz)2(H2O)2(γ-H4Mo8O26)]·2H2O (2), [CuII2(tea)2(H2O)6(HCr(OH)6Mo6O18)2]· 6H2O (3) and [AgI(bpz)(H2O)(γ-H4Mo8O26)0.5] (4) (bpz=4-butyl-1H-pyrazole,pz=1H-pyrazole,tea=2-[1,2,4]triazol-4-yl-ethylamine), have been hydrothermally synthesized and characterized by single-crystal X-ray diffraction analysis, IR spectra and elemental analyses. In compound1, there are two kinds of tri-nuclear CuIIclusters induced bybpzandpzligands, respectively. Four Anderson-type anions are linked by these tri-nuclear clusters to form a “W”-type subunit. In compound2, the [Cu(bpz)2(H2O)2]2+subunits connect theγ-Mo8anions to construct a chain. The remaining two non-coordinated N donors in [Cu(bpz)2(H2O)2]2+further link two adjacentγ-Mo8anions through Mo–N bonds. In compound3, there exists a bi-nuclear CuIIcluster [Cu2(tea)2(H2O)6]4+. The discrete bi-nuclear CuIIclusters and the CrMo6anions link each other through abundant hydrogen bonding interactions. In compound4, the [Ag(bpz)(H2O)]+subunits connectγ-Mo8anions to build a zigzag chain. The chains are further fused by other [Ag(bpz)(H2O)]+cations to form a grid-like layer. There still exist Mo–N bonds in4. We also have investigated the electrochemical and photocatalytic properties of1–4.

A Chain-like Polyoxotungstate Constructed from [CeW10O36]9–, [Na5(H2O)17Cl]4+, and [Na2(H2O)8]2+ Units: (NH4)3[Na5(H2O)17Cl]{[Na(H2O)4]2[CeW10O36]}· 6 H2O

2007 ◽  
Vol 62 (12) ◽  
pp. 1471-1475 ◽  
Author(s):  
Ling Yuan ◽  
Chao Qin ◽  
Xinlong Wang ◽  
Enbo Wang
Keyword(s):  
Hydrogen Bonding ◽  
Single Crystal ◽  
Supramolecular Network ◽  
X Ray Diffraction ◽  
Orthorhombic Space Group ◽  
Space Group ◽  
X Ray ◽  
Hydrogen Bonding Interactions ◽  
Linear Chains ◽  
A Chain

An unusual cerium-containing decaoxotungstate complex, (NH4)3[Na5(H2O)17Cl]{[Na(H2O)4]2- [CeW10O36]} · 6H2O (1) has been synthesized and characterized by IR, TG, and single crystal X-ray diffraction studies (yellow crystals, orthorhombic, space group Imm2, a = 11.473(2), b = 15.225(3), c = 17.646(7) Å, V = 3082.3(15) °A3, Z = 2, R = 0.046). In this compound, sandwichtype [CeW10O36]9− clusters are linked by binuclear [Na2(H2O)8]2+ units by sharing oxygen atoms into linear chains, which are further extended into a 2D supramolecular network via pentanuclear [Na5(H2O)17Cl]4+ units by strong hydrogen bonding interactions.

Molecular Cocrystals of Carboxylic Acids. IX. Carboxylic Acid Interactions With Organic Heterocyclic Bases. The Crystal Structures of the Adducts of (2,4-Dichlorophenoxy)acetic Acid With 3-Hydroxypyridine, 2,4,6-Trinitrobenzoic Acid With 2-Aminopyrimidine, and 4-Nitrobenzoic Acid With 3-Amino-1,2,4-triazole

1992 ◽  
Vol 45 (6) ◽  
pp. 969 ◽  
Author(s):  
KA Byriel ◽  
CHL Kennard ◽  
DE Lynch ◽  
G Smith ◽  
JG Thompson
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Crystal Structures ◽  
Carboxylic Acids ◽  
Spectroscopic Techniques ◽  
X Ray Diffraction ◽  
X Ray ◽  
Nitrobenzoic Acid ◽  
Dichlorophenoxy Acetic Acid ◽  
Heterocyclic Bases

The cocrystal adducts of a number of carboxylic acids with organic heterocyclic bases have been prepared, and their structures and intermolecular interactions interpreted through X-ray diffraction and infrared spectroscopic techniques. The crystal structures of three of these compounds, the 1 : 1 adducts [{(2,4-dich1orophenoxy)acetic acid)(3-hydroxypyridine)] (1), [(2,4,6-trinitrobenzoie acid)(2-aminopyrimidine)] (2), and [(4-nitrobenzoic acid)(3-amino- 1,2,4-trimole)] (3), have been determined by single-crystal X-ray diffraction and refined to residuals R 0.026, 0.033 and 0.040 for 1814, 1531 and 727 observed reflections, respectively.

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