Hydrogen-bonding patterns in the cocrystal 2,4-diamino-6-phenyl-1,3,5-triazine–sorbic acid (1/1)

2007 ◽  
Vol 63 (11) ◽  
pp. o4450-o4451 ◽  
Author(s):  
Kaliyaperumal Thanigaimani ◽  
Packianathan Thomas Muthiah ◽  
Daniel E. Lynch
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Sorbic Acid ◽  
Carboxyl Group ◽  
Amino Group ◽  
Acid Molecule ◽  
Asymmetric Unit ◽  
Graph Set ◽  
Bonding Patterns

In the title cocrystal, C9H9N5·C6H8O2, the asymmetric unit contains one 2,4-diamino-6-phenyl-1,3,5-triazine molecule and a sorbic acid molecule. The triazine molecules are base-paired [with a graph set of R 2 2(8)] on either side via N—H...N hydrogen bonds, forming a supramolecular ribbon along the c axis. Each triazine molecule interacts with the carboxyl group of a sorbic acid molecule via N—H...O and O—H...N hydrogen bonds, generating R 2 2(8) motifs. The supramolecular ribbons are interlinked by N—H...O hydrogen bonds involving the 2-amino group of the triazine molecules and the carboxyl O atom of the sorbic acid molecule.

scholarly journals Hydrogen-bonding patterns in 2-amino-4,6-dimethoxypyrimidine–4-aminobenzoic acid (1/1)

2006 ◽  
Vol 62 (7) ◽  
pp. o2976-o2978 ◽  
Author(s):  
Kaliyaperumal Thanigaimani ◽  
Packianathan Thomas Muthiah ◽  
Daniel E. Lynch
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Carboxyl Group ◽  
Acid Molecule ◽  
Aminobenzoic Acid ◽  
Graph Set ◽  
Supramolecular Chain ◽  
Bonding Patterns ◽  
Hydrogen Bonded

In the title cocrystal, C6H9N3O2·C7H7NO2, the 2-amino-4,6-dimethoxypyrimidine molecule interacts with the carboxyl group of the 4-aminobenzoic acid molecule through N—H...O and O—H...N hydrogen bonds, forming a cyclic hydrogen-bonded motif [R 2 2(8)]. This motif further self-organizes through N—H...O hydrogen bonds to generate an array of six hydrogen bonds with the rings having the graph-set notation R 2 3(6), R 2 2(8), R 4 2(8), R 2 2(8) and R 2 3(6). The 4-aminobenzoic acid molecules self-assemble via N—H...O hydrogen bonds to form a supramolecular chain along the c axis.

scholarly journals Crystal structure and Hirshfeld surface analysis of 2,4-diamino-6-phenyl-1,3,5-triazin-1-ium 4-methylbenzenesulfonate

2018 ◽  
Vol 74 (8) ◽  
pp. 1159-1162
Author(s):  
Ramalingam Sangeetha ◽  
Kasthuri Balasubramani ◽  
Kaliyaperumal Thanigaimani ◽  
Savaridasson Jose Kavitha
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Intermolecular Interactions ◽  
Hirshfeld Surface ◽  
Amino Group ◽  
Asymmetric Unit ◽  
Graph Set ◽  
Molecular Salt ◽  
Sulfonate Anion ◽  
Hydrogen Bonded

In the title molecular salt, C9H10N5 +·C7H7O3S−, the asymmetric unit consists of a 2,4-diamino-6-phenyl-1,3,5-triazin-1-ium cation and a 4-methylbenzenesulfonate anion. The cation is protonated at the N atom lying between the amine and phenyl substituents. The protonated N and amino-group N atoms are involved in hydrogen bonding with the sulfonate O atoms through a pair of intermolecular N—H...O hydrogen bonds, giving rise to a hydrogen-bonded cyclic motif with R 2 2(8) graph-set notation. The inversion-related molecules are further linked by four N—H...O intermolecular interactions to produce a complementary DDAA (D = donor, A = acceptor) hydrogen-bonded array, forming R 2 2(8), R 4 2(8) and R 2 2(8) ring motifs. The centrosymmetrically paired cations form R 2 2(8) ring motifs through base-pairing via N—H...N hydrogen bonds. In addition, another R 3 3(10) motif is formed between centrosymetrically paired cations and a sulfonate anion via N—H...O hydrogen bonds. The crystal structure also features weak S=O...π and π–π interactions. Hirshfeld surface and fingerprint plots were employed in order to further study the intermolecular interactions.

scholarly journals 2-[(E)-1,1-Dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2-benzothiazin-4-ylidene]acetic acid

2014 ◽  
Vol 70 (7) ◽  
pp. o775-o775
Author(s):  
Shaojuan Zhu ◽  
Shagufta Parveen ◽  
Changjin Zhu
Keyword(s):  
Hydrogen Bonding ◽  
Acetic Acid ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Chair Conformation ◽  
Asymmetric Unit ◽  
Compound C ◽  
Benzene Rings ◽  
Thiazine Ring ◽  
Graph Set

In the asymmetric unit of the title compound, C17H12F3NO4S, there are two conformationally similar molecules in which the heterocyclic thiazine ring adopts a half-chair conformation, with the dihedral angle between the two benzene rings being 24.84 (8) and 37.42 (8)°. In the crystal, the molecules form dimers through cyclic carboxylic acid O—H...O hydrogen-bonding associations [graph setR22(8)] and are extended into chains along [101] through weak C—H...Osulfinylhydrogen bonds [graph setR22(14)]..

scholarly journals (S)-Alanine–(S)-2-phenoxypropionic acid (1/1)

2012 ◽  
Vol 68 (6) ◽  
pp. o1720-o1720 ◽  
Author(s):  
Kiichi Amimoto ◽  
Yuma Nishioka
Keyword(s):  
Hydrogen Bonds ◽  
Electrostatic Interaction ◽  
Carboxylate Anion ◽  
Methyl Groups ◽  
Carboxyl Group ◽  
Acid Molecule ◽  
Zwitterionic Form ◽  
Phenyl Rings ◽  
Graph Set

In the title co-crystal, C3H7NO2·C9H10O3, the (S)-alanine molecule exists in the zwitterionic form stabilized by two pairs of N+—H...O− hydrogen bonds and an electrostatic interaction between the ammonium center and the carboxylate anion, forming a sheet along the ab plane. The carboxyl group of the (S)-2-phenoxypropionic acid molecule is connected to the top and bottom of the sheet via N+—H...O=C and O—H...O− [R 2 2(7) graph set] hydrogen bonds, giving an (S,S)-homochiral layer, in which both methyl groups of (S)-alanine and the phenyl rings of (S)-2-phenoxypropionic acid are oriented in the same direction along the b axis.

Comparison of hydrogen bonds and diverse weak interactions of the nitro group in 2-methyl-4-nitroanilinium nitrate, bisulfate and two hexafluoridosilicates: elementary graph-set approach

2016 ◽  
Vol 72 (6) ◽  
pp. 916-926 ◽  
Author(s):  
Marek Daszkiewicz ◽  
Agnieszka Mielcarek
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Nitro Group ◽  
Weak Interactions ◽  
Gradual Expansion ◽  
Graph Set ◽  
Mathematical Relations ◽  
Elementary Graph ◽  
Bonding Patterns

Crystal structures of (H2m4na)NO3(1), (H2m4na)HSO4(2), (H2m4na)2SiF6(3) and (H2m4na)2SiF6·2H2O (4), where 2m4na = 2-methyl-4-nitroaniline, are presented. Two layers of interactions occur in the structures, N—H...O/F hydrogen bonds and interactions with the nitro group. Although diverse, hydrogen-bonding patterns are compared with each other by means of interrelations among elementary graph-set descriptors and descriptors of hydrogen-bonding patterns. Using mathematical relations, the gradual expansion of the ring patterns was shown in the crystal structures. Parallel and perpendicular arranged nitro groups form weak π(N)NO2...π(O)NO2and π(N)NO2...ONO2interactions, respectively. The πNO2...πringinteraction has an impact to the stabilization of parallel oriented nitro groups. Generally, weak interactions constructed by the nitro group occur in the studied crystals as follows: π(N)NO2...π(O)NO2, πring...πring, C—H...O (1); π(N)NO2...π(O)NO2, π(N)NO2...ONO2(2); π(N)NO2...π(O)NO2, π(N)NO2...ONO2(3); C—H...O (4).

Hydrogen bonding in α-ferrocenyl alcohols: structures of 1-ferrocenylethanol, 1-ferrocenyl-2-phenylethanol, 1-ferrocenyl-1-phenylpropan-1-ol, 1-ferrocenyl-1-phenyl-2-methylpropan-1-ol, 1-ferrocenyl-1-phenyl-2,2-dimethylpropan-1-ol, 1-ferrocenyl-1,2-diphenylethanol and diferrocenyl(phenyl)methanol

1996 ◽  
Vol 52 (1) ◽  
pp. 110-121 ◽  
Author(s):  
C. Glidewell ◽  
R. B. Klar ◽  
P. Lightfoot ◽  
C. M. Zakaria ◽  
G. Ferguson
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Intermolecular Hydrogen Bonding ◽  
Asymmetric Unit ◽  
Common Occurrence ◽  
The Third ◽  
Graph Set ◽  
Dimeric Aggregates ◽  
Centrosymmetric Dimers ◽  
Isolated Molecules

The structure of 1-ferrocenylethanol (la), C12H14FeO, tetragonal, I41 cd, a = 23.3334 (18), c = 7.7186 (11) Å, Z = 16, R = 0.025 for 850 observations [I > 3σ(I)], contains spiral chains generated by a 41 axis, in which the molecules are connected by O—H...O hydrogen bonds in a motif with graph set C(2) with an O...O distance of 2.724 (3) Å. 1-Ferrocenyl-2-phenylethanol (If), C18H18FeO, orthorhombic, Pnaa, a = 9.8589 (7), b = 15.2800 (17), c = 19.1399 (17) Å, Z = 8, R = 0.036 for 1508 observations [I > 3σ(I)], crystallizes as dimeric aggregates lying across a crystallographic twofold axis and held together by O—H...O hydrogen bonds in a motif with graph set R 2 2(4) with an O...O distance of 2.868 (8) Å; there are also intramolecular O—H...π(C5H5) interactions. 1-Ferrocenyl-1-phenylpropan-1-ol (2b), C19H20FeO, monoclinic, P21/c, a = 10.2443 (13), b = 10.5811 (17), c = 14.2487 (12) Å, β = 100.190 (9)°, Z = 4, R = 0.029 for 2289 observations [I > 3σ(I)], crystallizes as isolated molecules containing O—H...π(C5H5) interactions. In 1-ferrocenyl-1-phenyl-2-methylpropan-1-ol (2c), C20H22FeO, monoclinic, Cc, a = 25.387 (4), b = 7.6825 (6), c = 17.803 (3) Å, β = 108.217 (17)°, Z = 8, R = 0.022 for 3286 observations [I > 3σ(I)], there are two molecules in the asymmetric unit, but the structure consists of isolated molecules containing O—H...π(C5H5) interactions. 1-Ferrocenyl-1-phenyl-2,2-dimethylpropan-1-ol (2d), C21H24FeO, monoclinic, P21/n, a = 8.007 (4), b = 13.002 (2), c = 66.24 (1) Å, β = 91.96 (3)°, Z = 16, R = 0.072 for 4130 observations [I > 3σ(I)], has four molecules in the asymmetric unit, but there is no intermolecular hydrogen bonding. The structure of 1-ferrocenyl-1,2-diphenylethanol (2f), C24H22FeO, monoclinic, C2/c, a = 26.229 (2), b = 5.889 (2), c = 24.553 (2) Å, β = 104.114 (11)°, Z = 8, R = 0.036 for 1733 observations [I > 2.5σ(I)], consists of isolated molecules in which the hydroxyl H atom is disordered unequally over three sites, each of which is trans to one of the C—C bonds involving C1; H atoms in two of these sites are involved in intramolecular O—H...π(C5H5) interactions and the H atom in the third is involved in an O—H...π(arene) interaction. The structure of diferrocenyl(phenyl)methanol (2g), C27H24Fe2O, triclinic, P{\bar 1}, a = 9.3999 (11), b = 11.1988 (16), c = 11.9720 (16) Å, a =117.844 (11), β = 98.890 (10), γ = 102.362 (11)°, Z = 2, R = 0.031 for 3435 observations [I > 2.5σ(I)], consists of centrosymmetric dimers held together by O—H...O hydrogen bonds in a motif with graph set R 2 2(4) with an O...O distance of 2.926 (4) Å; there are also intramolecular O—H...π(C5H5) interactions. Closed dimers containing the R 2 2(4) (OH)2 hydrogen-bonding motif, while unknown for purely organic alcohols, are a common occurrence in α-ferrocenyl alcohols (five examples from 13 known structures).

scholarly journals 2-Benzenesulfonamidobenzoic acid

2009 ◽  
Vol 65 (6) ◽  
pp. o1246-o1247 ◽  
Author(s):  
Abdullah Mohamed Asiri ◽  
Mehmet Akkurt ◽  
Salman A. Khan ◽  
Muhammad Nadeem Arshad ◽  
Islam Ullah Khan ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Title Compound ◽  
Crystal Packing ◽  
Carboxyl Group ◽  
Compound C ◽  
Hydrogen Bonding Interactions ◽  
Graph Set

In the title compound, C13H11NO4S, the dihedral angle between the planes of the benzene ring and the carboxyl group is 13.7 (1)°. The molecular structure contains intramolecular N—H...O and C—H...O hydrogen-bonding interactions, while the crystal packing is stabilized by C—H...O and O—H...O hydrogen bonds and C—H...π interactions. The O—H...O hydrogen bonds form a cyclic dimer, with graph-set motifR22(8), about a centre of symmetry.

scholarly journals Hydrogen-bonding patterns in 5-fluorocytosine–melamine co-crystal (4/1)

2016 ◽  
Vol 72 (4) ◽  
pp. 552-555 ◽  
Author(s):  
Marimuthu Mohana ◽  
Packianathan Thomas Muthiah ◽  
Liurukara D. Sanjeewa ◽  
Colin D. McMillen
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
The Other ◽  
Amino Group ◽  
Stacking Interactions ◽  
Asymmetric Unit ◽  
Twofold Axis ◽  
Ring Motif

The asymmetric unit of the title compound, 4C4H4FN3O·C3H6N6, comprises of two independent 5-fluorocytosine (5FC) molecules (AandB) and one half-molecule of melamine (M). The other half of the melamine molecule is generated by a twofold axis. 5FC moleculesAandBare linked through two different homosynthons [R22(8) ring motif]; one is formedviaa pair of N—H...O hydrogen bonds and the secondviaa pair of N—H...N hydrogen bonds. In addition to this pairing, the O atoms of 5FC moleculesAandBinteract with the N2 amino group on both sides of the melamine molecule, forming aDDAAarray of quadruple hydrogen bonds and generating a supramolecular pattern. The 5FC (moleculesAandB) and two melamine molecules interactviaN—H...O, N—H...N and N—H...O, N—H...N, C—H...F hydrogen bonds formingR66(24) andR44(15) ring motifs. The crystal structure is further strengthened by C—H...F, C—F...π and π–π stacking interactions.

scholarly journals Benzene-1,3,5-tricarboxylic acid–pyridinium-2-olate (1/3)

2014 ◽  
Vol 70 (4) ◽  
pp. o453-o454 ◽  
Author(s):  
José J. Campos-Gaxiola ◽  
Felipe Zamora Falcon ◽  
Ramón Corral Higuera ◽  
Herbert Höpfl ◽  
Adriana Cruz-Enríquez
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Tricarboxylic Acid ◽  
Dimensional Structure ◽  
Acid Molecule ◽  
Asymmetric Unit ◽  
Compound C ◽  
Dimensional Network ◽  
Graph Set

The asymmetric unit of the title compound, C9H6O6·3C5H5NO, contains one benzene-1,3,5-tricarboxylic acid molecule (BTA) and three pyridin-2-ol molecules each present in the zwitterion form. In the crystal, these entities are linked through O—H...O−and N+—H...O−hydrogen bonds, forming sheets parallel to (10-1). These layers contain macrocyclic rings of composition [BTA]2[pyol]6and with graph-set notationR68(44), which are stacked alongcthrough π–π interactions [inter-centroid distances = 3.536 (2)–3.948 (3) Å]. They are interconnected by N+—H...O−hydrogen-bonded chains of pyridin-2-ol molecules running parallel toc, forming a three-dimensional network. There are also C—H...O hydrogen bonds present which reinforce the three-dimensional structure.

The effect of partial methylation of the glycine amino group on crystal structure inN,N-dimethylglycine and its hemihydrate

2012 ◽  
Vol 68 (8) ◽  
pp. o283-o287 ◽  
Author(s):  
Vasily S. Minkov ◽  
Elena V. Boldyreva
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Water Molecules ◽  
Amino Group ◽  
Asymmetric Unit ◽  
Partial Methylation ◽  
Space Groups ◽  
Carboxylate Groups ◽  
Anhydrous Compound ◽  
Additional Hydrogen

N,N-Dimethylglycine, C4H9NO2, and its hemihydrate, C4H9NO2·0.5H2O, are discussed in order to follow the effect of the methylation of the glycine amino group (and thus its ability to form several hydrogen bonds) on crystal structure, in particular on the possibility of the formation of hydrogen-bonded `head-to-tail' chains, which are typical for the crystal structures of amino acids and essential for considering amino acid crystals as mimics of peptide chains. Both compounds crystallize in centrosymmetric space groups (PbcaandC2/c, respectively) and have twoN,N-dimethylglycine zwitterions in the asymmetric unit. In the anhydrous compound, there are no head-to-tail chains but the zwitterions formR44(20) ring motifs, which are not bonded to each other by any hydrogen bonds. In contrast, in the crystal structure ofN,N-dimethylglycinium hemihydrate, the zwitterions are linked to each other by N—H...O hydrogen bonds into infiniteC22(10) head-to-tail chains, while the water molecules outside the chains provide additional hydrogen bonds to the carboxylate groups.

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