π‐Stacked hydrogen‐bonded dimers in 2‐(2‐nitro­phenyl­amino­carbonyl)­benzoic acid,and hydrogen‐bonded sheets in orthorhombic and monoclinic polymorphs of 2‐(4‐nitro­phenyl­amino­carbonyl)­benzoic acid

Molecules of 2‐(2‐nitrophenylaminocarbonyl)benzoic acid, C₁₄H₁₀N₂O₅, are linked into centrosymmetric R(8) dimers by a single O—H⋯O hydrogen bond [H⋯O = 1.78 Å, O⋯O = 2.623 (2) Å and O—H⋯O = 178°] and these dimers are linked into sheets by a single aromatic π–π stacking interaction. The isomeric compound 2‐(4‐nitrophenylaminocarbonyl)benzoic acid crystallizes in two polymorphic forms. In the orthorhombic form (space group P2₁2₁2₁ with Z′ = 1, crystallized from ethanol), the mol­ecules are linked into sheets of R(22) rings by a combination of one N—H⋯O hydrogen bond [H⋯O = 1.96 Å, N⋯O = 2.833 (3) Å and N—H⋯O = 171°] and one O—H⋯O hydrogen bond [H⋯O = 1.78 Å, O⋯O = 2.614 (3) Å and O—H⋯O = 173°]. In the monoclinic form (space group P2₁/n with Z′ = 2, crystallized from acetone), the mol­ecules are linked by a combination of two N—H⋯O hydrogen bonds [H⋯O = 2.09 and 2.16 Å, N⋯O = 2.873 (4) and 2.902 (3) Å, and N—H⋯O = 147 and 141°] and two O—H⋯O hydrogen bonds [H⋯O = 1.84 and 1.83 Å, O⋯O = 2.664 (3) and 2.666 (3) Å, and O—H⋯O = 166 and 174°] into sheets of some complexity. These sheets are linked into a three‐dimensional framework by a single C—H⋯O hydrogen bond [H⋯O = 2.45 Å, C⋯O = 3.355 (4) Å and C—­H⋯O = 160°].     

(Z)‐6‐{[1,3‐Dihydroxy‐2‐(hydroxy­methyl)propan‐2‐ylamino]methyl­ene}‐2‐methoxy‐4‐[(E)‐o‐tolyl­diazenyl]­cyclo­hexa‐2,4‐dienone

The title compound, C₁₉H₂₃N₃O₅, adopts the keto–amine tautomeric form with the hydr­oxy H atom located on the N atom, where it is involved in a strong intra­molecular N—H⋯O hydrogen bond. The compound exhibits trans geometry with respect to the azo N=N double bond, with a dihedral angle between the two benzene rings of 38.03 (6)°. The packing of the mol­ecules in the crystal structure is determined by O—H⋯O and C—H⋯O hydrogen bonds. A comparison with closely related compounds is given.     

2‐[(2‐Hydro­xy‐4‐nitro­phenyl)­amino­methyl­ene]­cyclo­hexa‐3,5‐dien‐1(2H)‐one

The title compound, C₁₃H₁₀N₂O₄, adopts the keto–amine tautomeric form and displays an intramolecular N—H⋯O [N⋯O = 2.579 (2) Å] and three intermolecular O—H⋯O [O⋯O = 2.561 (2) Å] and C—H⋯O [C⋯O = 3.274 (2) and 3.318 (2) Å] hydrogen bonds. The keto–amine structure is favoured by through‐mol­ecule conjugation between the hydroxy O atom and imine N atom. The dihedral angle between the planes of the two aromatic rings is 10.79 (4)°.     

2‐Amino‐5‐nitro­thia­zole monoethanol solvate: triply‐interwoven hydrogen‐bonded sheets containing centrosymmetric R(8) and R(38) rings

2‐Amino‐5‐nitro­thia­zole crystallizes from solution in ethanol as a monosolvate, C₃H₃N₃O₂S·C₂H₆O, in which the thia­zole component has a strongly polarized molecular–electronic structure. The thia­zole mol­ecules are linked into centrosymmetric dimers by paired N—H⋯N hydrogen bonds [H⋯N = 2.09 Å, N⋯N = 2.960 (6) Å and N—H⋯N = 169°], and these dimers are linked by the ethanol mol­ecules, via a two‐centred N—H⋯O hydrogen bond [H⋯O = 1.98 Å, N⋯O = 2.838 (5) Å and N—H⋯O = 164°] and a planar asymmetric three‐centred O—H⋯(O)₂ hydrogen bond [H⋯O = 2.07 and 2.53 Å, O⋯O = 2.900 (5) and 3.188 (5) Å, O—H⋯O = 169 and 136°, and O⋯H⋯O = 55°], into sheets built from alternating (8) and (38) rings. These sheets are triply interwoven.     

5‐(2‐Chloro­phenyl­diazenyl)­salicyl­aldehyde and 4‐(2‐chloro­phenyl­diazenyl)‐2‐{[tris­(hydroxy­methyl)­methyl]­amino­methyl­ene}cyclo­hexa‐3,5‐dien‐1(2H)‐one

The mol­ecule of the former title compound, C₁₃H₉ClN₂O₂, (I), is nearly planar, with an intramolecular O⋯O hydrogen bond of 2.692 (2) Å. The latter title compound, C₁₇H₁₈ClN₃O₄, (II), exists in the keto–amine tautomeric form, with a strong intramolecular hydrogen bond of 2.640 (2) Å between the O and N atoms, the H atom being bonded to the N atom. The azo­benzene moieties of both mol­ecules have trans configurations, and the dihedral angle between the planes of the two aromatic rings is 4.1 (1)° in (I) and 9.9 (1)° in (II). The N—H⋯O hydrogen‐bonded rings are almost planar and coupled with the cyclo­hexa­diene rings in (II).     

5‐Amino‐3‐tert‐butyl‐1‐(4‐nitro­phen­yl)‐1H‐pyrazole forms hydrogen‐bonded sheets of alternating R(20) and R(32) rings

Molecules of the title compound, C₁₃H₁₆N₄O₂, are linked by one N—H⋯O hydrogen bond [H⋯O = 2.47 Å, N⋯O = 3.326 (2) Å and N—H⋯O = 166°] and one N—H⋯N hydrogen bond [H⋯N = 2.19 Å, N⋯N = 3.063 (2) Å and N—H⋯N = 173°] into sheets containing alternating (20) and (32) rings, both types of which are centrosymmetric.     

4‐[(2‐Chloro­phenyl)­diazenyl]‐6‐methoxy‐2‐{[tris­(hydroxy­methyl)­methyl]­amino­methyl­ene}cyclo­hexa‐3,5‐dien‐1(2H)‐one

The structure of the title compound, C₁₈H₂₀ClN₃O₅, displays the characteristic features of azo­benzene derivatives. Intramolecular N—H⋯O, weak intramolecular C—H⋯O, and intermolecular O—H⋯O and C—H⋯O interactions influence the conformation of the mol­ecules and the crystal packing. Intermolecular hydrogen bonds link the mol­ecules into infinite chains, and the title compound adopts the keto–amine tautomeric form. The azo­benzene moiety of the mol­ecule has a trans configuration. The mol­ecule is not planar, and the dihedral angle between the two phenyl rings is 35.6 (2)°.     

Three N2‐benzoyl­oxybenz­amidines: sheet structures built from hard and soft hydrogen bonds and aromatic π–π stacking interactions

Molecules of the title compounds N²‐(benzoyl­oxy)­benz­ami­dine, C₁₄H₁₂N₂O₂, (I), N²‐(2‐hydroxy­benzoyl­oxy)­benz­ami­dine, C₁₄H₁₂N₂O₃, (II), and N²‐benzoyloxy‐2‐hydroxybenzamidine, C₁₄H₁₂N₂O₃, (III), all have extended chain conformations, with the aryl groups remote from one another. In (I), the mol­ecules are linked into chains by a single N—H⋯N hydrogen bond [H⋯N = 2.15 Å, N⋯N = 3.029 (2) Å and N—H⋯N = 153°] and these chains are linked into sheets by means of aromatic π–π stacking interactions. There is one intramolecular O—H⋯O hydrogen bond in (II), and a combination of one three‐centre N—H⋯(N,O) hydrogen bond [H⋯N = 2.46 Å, H⋯O = 2.31 Å, N⋯N = 3.190 (2) Å, N⋯O = 3.146 (2) Å, N—H⋯N = 138° and N—H⋯O = 154°] and one two‐centre C—H⋯O hydrogen bond [H⋯O = 2.46 Å, C⋯O = 3.405 (2) Å and C—H⋯O = 173°] links the mol­ecules into sheets. In (III), an intramolecular O—H⋯N hydrogen bond and two N—H⋯O hydrogen bonds [H⋯O = 2.26 and 2.10 Å, N⋯O = 2.975 (2) and 2.954 (2) Å, and N—H⋯O = 138 and 163°] link the molecules into sheets.     

Ethyl N‐[2‐(hydroxy­acetyl)­phenyl]­carbamate,ethyl N‐[2‐(hydroxy­acetyl)‐4‐iodo­phenyl]­carbamate and ethyl N‐[2‐(hydroxy­acetyl)‐4‐methyl­phenyl]­carbamate

In ethyl N‐[2‐(hydroxy­acetyl)phenyl]carbamate, C₁₁H₁₃NO₄, all of the non‐H atoms lie on a mirror plane in the space group Pnma; the mol­ecules are linked into simple chains by a single C—H⋯O hydrogen bond. The mol­ecules of ethyl N‐[2‐(hydroxy­acetyl)‐4‐iodo­phenyl]carbamate, C₁₁H₁₂INO₄, are linked into sheets by a combination of O—H⋯I and C—H⋯O hydrogen bonds and a dipolar I⋯O contact. Ethyl N‐­[2‐(hydroxy­acetyl)‐4‐methyl­phenyl]carbamate, C₁₂H₁₅NO₄, crystallizes with Z′ = 2 in the space group P; pairs of mol­ecules are weakly linked by an O—H⋯O hydrogen bond and these aggregates are linked into chains by two independent aromatic π–π stacking inter­actions.     

4‐Amino‐7‐(2‐de­oxy‐2‐fluoro‐β‐d‐arabinofuranos­yl)‐5‐fluoro‐7H‐pyrrolo[2,3‐d]pyrimidine: a bis‐fluorinated analogue of 2′‐deoxy­tubercidin

The title compound, C₁₁H₁₂F₂N₄O₃, exhibits an anti glycosylic bond conformation, with a torsion angle χ = −117.8 (2)°. The sugar pucker is N‐type (C4′‐exo, between ³T₄ and E₄, with P = 45.3° and τ_m = 41.3°). The conformation around the exocyclic C—C bond is −ap (trans), with a torsion angle γ = −177.46 (15)°. The nucleobases are stacked head‐to‐head. The crystal structure is characterized by a three‐dimensional hydrogen‐bond network involving N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds.     

1,3‐Bis[2‐(2‐hydroxybenzylideneamino)phenoxy]propane

The title compound {systematic name: 2,2′‐[1,3‐propanediyldioxydi‐o‐phenylenebis(nitrilomethylidyne)]diphenol}, C₂₉H₂₆N₂O₄, exists as the phenol–imine form in the crystal, and there are strong intramolecular O—H⋯N hydrogen bonds, with O⋯N distances of 2.545 (2) and 2.579 (2) Å. The C=N imine bond distances are in the range 1.276 (2)–1.279 (2) Å and the C=N—C bond angles are in the range 123.05 (16)–124.64 (17)°. The configurations about the C=N bonds are anti (1E).     

N,N‐Di­methyl­anilinium 3‐cyano‐4‐(di­cyano­methyl­ene)‐5‐oxo‐4,5‐di­hydro‐1H‐pyrrol‐2‐olate

In the title compound, C₈H₁₂N⁺·C₈HN₄O₂⁻, the anion and cation lie on a crystallographic mirror plane and form planar ribbons via N—H⋯O [N⋯O = 2.933 (4) Å, H⋯O = 2.01 Å and N—H⋯O = 170°] and N—H⋯N [N⋯N = 3.016 (5) Å, H⋯N = 2.15 Å and N—H⋯N = 169°] hydrogen bonds. The ribbons are further linked via weak C—H⋯O and C—H⋯N hydrogen bonds. In adjacent planes, anions lie opposite cations; π–π interactions (separation a/2 = 3.520 Å) exist between the anions and the cations, and stacks are formed, running along the a axis. The cations are disordered over two interpenetrating sites, with occupancies of 0.833 (5) and 0.167 (5).     

catena‐Poly­[[(di‐2‐pyridyl­amine)­silver(I)]‐μ‐nicotinato] and catena‐poly­[[(di‐2‐pyridyl­amine)silver(I)]‐μ‐2,6‐di­hydroxy­benzoato]

In catena‐poly­[[(di‐2‐pyridyl­amine‐κ²N,N′)silver(I)]‐μ‐nico­tinato‐κ²N:O], [Ag(C₆H₄NO₂)(C₁₀H₉N₃)]_n, the Ag^I atom is tetracoordinated by two N atoms from the di‐2‐pyridyl­amine (BPA) ligand [Ag—N = 2.3785 (18) and 2.3298 (18) Å] and by one N atom and one carboxyl­ate O atom from nicotinate ligands [Ag—N = 2.2827 (15) Å and Ag—O = 2.3636 (14) Å]. Bridging by nicotinate N and O atoms generates a polymeric chain structure, which extends along [100]. The carboxyl O atom not bonded to the Ag atom takes part in an intrachain C—H⋯O hydrogen bond, further stabilizing the chain. Pairs of chains are linked by N—H⋯O hydrogen bonds to generate ribbons. There are no π–π interactions in this complex. In catena‐poly­[[(di‐2‐pyridyl­amine‐κ²N,N′)silver(I)]‐μ‐2,6‐di­hydroxy­benzoato‐κ²O¹:O²], [Ag(C₇H₅O₄)(C₁₀H₉N₃)]_n, the Ag^I atom has a distorted tetrahedral coordination, with three strong bonds to two pyridine N atoms from the BPA ligand [Ag—N = 2.286 (5) and 2.320 (5) Å] and to one carboxyl­ate O atom from the 2,6‐di­hydroxy­benzoate ligand [Ag—O = 2.222 (4) Å]; the fourth, weaker, Ag‐atom coordination is to one of the phenol O atoms [Ag⋯O = 2.703 (4) Å] of an adjacent moiety, and this interaction generates a polymeric chain along [100]. Pairs of chains are linked about inversion centers by N—H⋯O hydrogen bonds to form ribbons, within which there are π–π interactions. The ribbons are linked about inversion centers by pairs of C—H⋯O hydrogen bonds and additional π–π interactions between inversion‐related pairs of 2,6‐di­hydroxy­benzoate ligands to generate a three‐dimensional network.     

Tris(1H‐benzimidazol‐2‐yl­meth­yl)­amine–solvent adducts

The tris­(1H‐benzimidazol‐2‐yl­meth­yl)­amine (ntb) mol­ecule crystallizes in different solvent systems, resulting in two kinds of adduct, namely the monohydrate, C₂₄H₂₁N₇·H₂O or ntb·H₂O, (I), and the acetonitrile–methanol–water (1/0.5/1.5) solvate, C₂₄H₂₁N₇·C₂H₃N·0.5CH₄O·1.5H₂O or ntb·1.5H₂O·0.5MeOH·MeCN, (II). In both cases, ntb adopts a tripodal mode to form hydrogen bonds with a solvent water mol­ecule via two N—H⋯O and one O—H⋯N hydrogen bond. In (I), the ntb·H₂O adduct is further assembled into a two‐dimensional network by N—H⋯N and O—H⋯N hydrogen bonds, while in (II), a double‐stranded one‐dimensional chain structure is assembled via N—H⋯O and O—H⋯O hydrogen bonds, with the acetonitrile mol­ecules located inside the cavities of the chain structure.     

(2S,RS)‐6‐Phenyl‐1‐(p‐tolyl­sulfinyl)­hexa‐3(E),5(E)‐dien‐2‐ol

The mol­ecule of the title compound, C₁₉H₂₀O₂S, corresponds to a chiral sulfinyldienol with two stereogenic centres, viz. the C atom susbtituted by the hydr­oxy group and the sulfinyl S atom. The mol­ecule displays a V‐shape in the solid state. The dihedral angle defined by the least‐squares planes of the aromatic rings is 72.9 (1)°. The packing pattern exhibits the following inter­molecular hydrogen bonds: one O—H⋯O [H⋯O = 1.98 Å, O⋯O = 2.785 (4) Å and O—H⋯O = 166°] and two C—H⋯O [H⋯O = 2.58 and 2.60 Å, C⋯O = 3.527 (5) and 3.347 (5) Å, and C—H⋯O = 164 and 134°]. These define a chain along b.     

Bilayers in 4‐iodo‐N‐(2‐iodo‐4‐nitrophenyl)benzamide generated by a combination of an N—H⋯O=C hydrogen bond and two independent iodo–nitro interactions

Molecules of the title compound, C₁₃H₈I₂N₂O₃, are linked into C(4) chains by a single N—H⋯O=C hydrogen bond [H⋯O = 2.10 Å, N⋯O = 2.832 (5) Å and N—H⋯O = 140°]. Two independent two‐centre iodo–nitro interactions, both involving the same O atom but different I atoms [I⋯O = 3.205 (3) and 3.400 (3) Å, and C—I⋯O = 160.4 (2) and 155.7 (2)°], link the hydrogen‐bonded chains into bilayers.     

4‐Amino‐3‐methyl‐6‐phenyl‐1,2,4‐triazin‐5(4H)‐one (metamitron) and 4‐amino‐6‐methyl‐3‐phenyl‐1,2,4‐triazin‐5(4H)‐one (isometamitron)

The title structures, both C₁₀H₁₀N₄O, are substitutional isomers. The N—N bond lengths are longer and the C=N bond lengths are shorter by ca 0.025 Å than the respective average values in the C=N—N=C group of asymmetric triazines; the assessed respective bond orders are 1.3 and 1.7. There are N—H⋯O and N—H⋯N hydrogen bonds in both structures, with 4‐­amino‐3‐methyl‐6‐phenyl‐1,2,4‐triazin‐5(4H)‐one containing a rare bifurcated N—H⋯N,N hydrogen bond. The structures differ in their mol­ecular stacking and the hydrogen‐bonding patterns.     

2‐[Benzoyl­(hydroxy­imino)­methyl­amino]­benzoic acid

The structure of the title compound, C₁₅H₁₂N₂O₄, consists of a polymeric arrangement, around inversion centres, of mol­ecules linked through O—H⋯N and O—H⋯O hydrogen bonds; there are also intramolecular hydrogen bonds. All these hydrogen‐bond interactions result in the formation of infinite chains parallel to the [010] direction. The oxime group has an E conformation.     

6‐Amino‐2‐(3,4‐di­methoxy­benzyl­amino)‐3‐methyl‐5‐nitro­so­pyrimidin‐4(3H)‐one: hydrogen‐bonded sheets form interdigitated bilayers

Molecules of the title compound, C₁₄H₁₇N₅O₄, exhibit a highly polarized molecular–electronic structure. The mol­ecules are linked into sheets by two N—H⋯O hydrogen bonds [H⋯O = 2.03 and 2.02 Å, N⋯O = 2.836 (2) and 2.887 (2) Å, and N—H⋯O = 153 and 168°], augmented by a single C—H⋯O hydrogen bond [H⋯O = 2.47 Å, C⋯O = 3.403 (2) Å and C—H⋯O = 166°]. Pairs of sheets, related by inversion, form bilayers with interdigitated di­methoxy­benzyl substituents, weakly linked by a further C—H⋯O interaction [H⋯O = 2.50 Å, C⋯O = 3.350 (2) Å and C—H⋯O = 146°].     

Poly­sulfonyl­amines. CLXXI. [Di­(methane­sulfonyl)­amido‐κN]­bis(2‐picoline‐κN)copper(I)

The title compound, [Cu(C₂H₆NO₄S₂)(C₆H₇N)₂], consists of monomeric mol­ecules in which the Cu atom displays planar but irregular coordination by three N‐atom donors; Cu—N = 2.1054 (12) (amide N), 1.9514 (12) and 1.9589 (12) Å, and N—Cu—N = 141.24 (5), 111.54 (5) and 107.20 (5)°. Intramolecular Cu⋯O contacts are observed. The packing involves (interconnected) layer formation via C—H⋯O interactions in two directions, three hydrogen bonds combining to form layers parallel to (101) and five to form layers parallel to (10).