4,4′‐Tri­methyl­enedipyridinium bis­[carboxy­methyl­phos­pho­nate(1–)]: a three‐dimensional framework structure built from O—H⃛O,N—H⃛O and C—H⃛O hydrogen bonds

In the title compound, C₁₃H₁₆N₂²⁺·2C₂H₄O₅P⁻, the cation lies across a twofold rotation axis in space group Fdd2. The anions are linked into molecular ladders by two O—H⃛O hydrogen bonds [H⃛O = 1.73 and 1.77 Å, O⃛O = 2.538 (2) and 2.598 (3) Å, and O—H⃛O = 160 and 170°], these ladders are linked into sheets by a single type of N—H⃛O hydrogen bond [H⃛O = 1.75 Å, N⃛O = 2.624 (3) Å and N—H⃛O = 171°] and the sheets are linked into a three‐dimensional framework by a single type of C—H⃛O hydrogen bond [H⃛O = 2.48 Å, C⃛O = 3.419 (4) Å and C—H⃛O = 167°].     

4‐Iodo‐N‐(2‐nitro­phenyl­sulfanyl)­aniline: π‐stacked sheets generated by a combination of N—H⃛O and C—H⃛O hydrogen bonds

Molecules of the title compound, C₁₂H₉IN₂O₂S, are linked by one N—H⃛O hydrogen bond [H⃛O = 2.16 Å, N⃛O = 2.935 (4) Å and N—H⃛O 147°] and two C—H⃛O hydrogen bonds [H⃛O both 2.49 Å, C⃛O = 3.231 (5) and 3.220 (5) Å, and C—H⃛O = 135 and 134°] into sheets which themselves are weakly linked by an aromatic π–π‐stacking interaction between iodinated rings in centrosymmetrically related mole­cules. There are no iodo–nitro interactions.     

N‐(6‐Amino‐3,4‐di­hydro‐3‐methyl‐5‐nitro­so‐4‐oxopyrimidin‐2‐yl)‐(S)‐glutamic acid: a three‐dimensional framework structure built from O—H⃛O,N—H⃛O and O—H⃛N hydrogen bonds

The title compound, C₁₀H₁₃N₅O₆, exhibits a highly polarized molecular–electronic structure and the conformation is influenced by two intramolecular N—H⃛O hydrogen bonds. The mol­ecules are linked into a single framework by hydrogen bonds of types O—H⃛O [O—H = 1.22, H⃛O = 1.38, O⃛O = 2.558 (6) Å and O—H⃛O = 160°], N—H⃛O [H⃛O = 2.26, N⃛O = 2.866 (6) Å and N—H⃛O = 126°] and O—H⃛N [O—H = 1.26, H⃛N = 1.56, O⃛N = 2.811 (6) Å and O—H⃛N = 170°]. The substructure generated by the O—H⃛O and N—H⃛O hydrogen bonds takes the form of a double helix.     

meso‐5,5,7,12,12,14‐Hexamethyl‐1,4‐diaza‐8,11‐diazoniacyclotetradecane bis(2‐naphthoate) ethanol disolvate: centrosymmetric five‐component aggregates linked into sheets by C—H⃛π(arene) hydrogen bonding

The title compound is an ethanol‐solvated salt, C₁₆H₃₈N₄²⁺·2C₁₁H₇O₂⁻·2C₂H₆O, in which the cation lies across a centre of inversion in P2₁/c. The ions are linked by N—H⃛O hydrogen bonds [H⃛O = 1.70 and 2.30 Å, N⃛O = 2.624 (2) and 3.136 (2) Å, and N—H⃛O = 178 and 151°], and the ethanol mol­ecule is linked to the anion by an O—H⃛O hydrogen bond [H⃛O = 1.90 Å, O⃛O = 2.728 (2) Å and O—H⃛O = 171°], to form a centrosymmetric five‐component aggregate. C—H⃛O hydrogen bonds and aromatic π–π‐stacking interactions are absent, but the aggregates are linked into sheets by a single C—H⃛π(arene) hydrogen bond.     

5‐[N‐(1H‐Benzotriazol‐1‐yl­methyl)­amino]‐3‐tert‐butyl‐1‐phenyl­pyrazole: sheets built from N—H⋯N,C—H⋯N and C—H⋯π(pyrazole) interactions

In the title compound, C₂₀H₂₂N₆, the mol­ecules are linked into a chain of rings by N—H?N [H?N 2.16 Å, N?N 2.950 (3) Å and N—H?N 149°] and C—H?N [H?N 2.55 Å, C?N 3.481 (3) Å and C—H?N 165°] hydrogen bonds, and these chains are linked into sheets by means of C—­H?π(pyrazole) interactions.     

Hydro­gen bonding and C—H⃛O interactions in 4‐phenanthrenemethanol at 150 K

The title compound, C₁₅H₁₂O, crystallizes in the centrosymmetric space group I4₁/a with one mol­ecule in the asymmetric unit. In the single hydrogen bond, the H atom is ordered, the O_D?O_A distance is 2.788 (1) Å and the O—H?O angle is 176 (1)°. Each hydroxyl group forms hydrogen bonds with two other hydroxyl groups and the resulting chains of interactions, in four non‐linked subsets of mol­ecules, propagate along [001]. The single leading intermolecular C—H?O interaction has an H?O distance of 2.81 Å and a C—H?O angle of 140°; the single leading intramolecular C—H?O interaction has an H?O distance of 2.24 Å and a C—H?O angle of 152°. The phenanthrene core is less nearly planar in this structure than in the room temperature structure of phenanthrene‐4‐carboxylic acid.     

μ‐1,4‐Benzenedicarboxylato‐bis[trans‐aqua(1,4,8,11‐tetraazacyclotetradecane)nickel(II)] diperchlorate forms a three‐dimensional hydrogen‐bonded framework

The title compound, [Ni₂(C₈H₄O₄)(C₁₀H₂₄N₄)₂(H₂O)₂](ClO₄)₂, contains two independent octahedral Ni^II centres with trans‐NiN₄O₂ chromophores. The bridging benzene­dicarboxyl­ate ligand is bonded to the two Ni atoms, each via one O atom of each carboxyl­ate, while the other O atom participates in an intramolecular N—H?O hydrogen bond, forming an S(6) motif. The cations are linked to the perchlorate anions via O—H?O and N—H?O hydrogen bonds [O?O 2.904 (6) and 2.898 (6) Å; O—H?O 158 (6) and 165 (6)°; N?O 3.175 (7) and 3.116 (7) Å; N—H?O 168 and 166°] to form molecular ladders. These ladders are linked by further O—H?O and N—H?O hydrogen bonds [O?O 2.717 (6) and 2.730 (5) Å; O—H?O 170 (4) and 163 (6)°; N?O 3.373 (7) and 3.253 (7) Å; N—H?O 163 and 167°] to form a continuous three‐dimensional framework. The perchlorate anions both participate in three hydrogen bonds, and both are thus fully ordered.     

Soft C—H⃛O hydrogen bonds in methyl 2,4‐di­nitro­benzene­sulfenate: sheets built from R22(10) and R66(42) rings

Molecules of the title compound, C₇H₆N₂O₅S, are linked into sheets containing R₂²(10) and R₆⁶(42) rings by C—H?O hydrogen bonds [C?O 3.405 (3) and 3.511 (2) Å; C—H?O 159 and 169°], in which both acceptors are in the same nitro group. Comparisons are made with the hydrogen bonding in other nitro­benzene­sulfenate esters.     

A quasi‐diamondoid hydrogen‐bonded framework in an­hydro­us sulfanilic acid

The title compound (C₆H₇NO₃S) exists as a zwitterion (4‐ammonio­benzene­sulfonate), ⁺H₃NC₆H₄SO₃^?, and these units are linked into a three‐dimensional framework by two distinct two‐centre N—H?O hydrogen bonds [H?O 1.84 and 1.87 Å; N?O 2.767 (2) and 2.746 (2) Å; N—H?O 166 and 172°] and a planar three‐centre N—H?(O)₂ hydrogen bond [H?O 2.03 and 2.37 Å; N?O 2.816 (2) and 2.877 (2) Å; N—H?O 162 and 111°; O?H?O 86°].     

Hydro­gen bonding in substituted nitro­anilines: isolated nets in 1,3‐­diamino‐4‐nitrobenzene and continuously interwoven nets in 3,5‐­dinitro­aniline

Molecules of 1,3‐diamino‐4‐nitrobenzene, C₆H₇N₃O₂, are linked by N—H?O hydrogen bonds [N?O 2.964 (2) and 3.021 (2) Å; N—H?O 155 and 149°] into (4,4) nets. In 3,5‐di­nitro­aniline, C₆H₅N₃O₄, where Z′ = 2, the mol­ecules are linked by three N—H?O hydrogen bonds [N?O 3.344 (2)–3.433 (2) Å and N—H?O 150–167°] into deeply puckered nets, each of which is interwoven with its two immediate neighbours.     

Hydro­gen‐bonded molecular ladders in trans‐1,2‐bis(2‐nitro­anilino)­cyclo­hexane

Crystals of the title compound, C₁₈H₂₀N₄O₄, contain equal numbers of (R,R) and (S,S) mol­ecules, but these are not precise enantiomorphs, neither are they related by crystallographic symmetry; in addition, each mol­ecule exhibits approximate, but not exact, twofold rotational symmetry. There are intramolecular N—H?O hydrogen bonds [N?O 2.609 (4)–2.638 (5) Å; N—H?O 125–132°] and the mol­ecules are linked into molecular ladders by C—H?O hydrogen bonds [C?O 3.306 (6)–3.386 (6) Å; C—H?O 146–160°].     

meso‐5,5,7,12,12,14‐Hexa­methyl‐4,11‐di­aza‐1,8‐diazo­nia­cyclo­tetra­decane (S)‐malate(2–) methanol disolvate: a chain of rings generated by two pairs of N—H⃛O hydrogen bonds

The title compound is a methanol‐solvated salt, C₁₆H₃₈N₄²⁺·C₄H₄O₅²⁻·2CH₃OH, in which the ionic components are linked into chains by two pairs of N—H⃛O hydrogen bonds [H⃛O = 1.78–2.21 Å, N⃛O = 2.702 (14)–3.094 (8) Å and N—H⃛O = 160–179°]. The methanol mol­ecules are pendent from the chain and are linked to it by O—H⃛O hydrogen bonds [H⃛O = 1.86 and 1.89 Å, O⃛O = 2.691 (9) and 2.708 (16) Å, and O—H⃛O = 168 and 165°].     

Phthal­imide at 120 K: perforated molecular ribbons containing three different ring motifs

Molecules of phthal­imide [1H‐iso­indole‐1,3(2H)‐dione], C₈H₅NO₂, are linked by N—H?O hydrogen bonds [H?O 2.02 Å, N?O 2.8781 (16) Å and N—H?O 167°] and by C—H?O hydrogen bonds [H?O 2.54 and 2.56 Å, C?O 3.3874 (18) and 3.4628 (19) Å, and C—H?O 149 and 159°] into molecular ribbons, which are pierced by three different ring motifs; there are two centrosymmetric R(8) rings, each containing a single hydrogen bond, N—H?O in one case and C—H?O in the other, and R(9) rings containing all three hydrogen bonds.     

Bis(4‐hydroxy­benzoato‐O)(1,4,8,11‐tetra­aza­cyclo­tetra­decane‐κ4N)nickel(II): a three‐dimensional framework built from O—H⋯O and N—H⋯O hydrogen bonds

The title compound, [Ni(C₇H₅O₃)₂(C₁₀H₂₄N₄)], contains octahedral Ni^II in a centrosymmetric trans configuration with Ni—N distances of 2.0637 (17) and 2.0699 (16) Å and an Ni—O distance of 2.1100 (14) Å. The mol­ecules are linked by a single type of O—H?O hydrogen bond [O?O 2.618 (2) Å and O—H?O 161°] into two‐dimensional sheets; a singletype of N—H?O hydrogen bond [N?O 2.991 (2) Å and N—H?O 139°] links these sheets into a three‐dimensional framework.     

N‐Propionylhydroxylamine forms a three‐dimensional hydrogen‐bonded framework structure

The title compound, N‐hydroxy­propan­amide, C₃H₇NO₂, crystallizes with Z′ = 3 in P2₁/c. The mol­ecules are linked by three N—H?O hydrogen bonds [N?O 2.8012 (16) to 2.8958 (15) Å; N—H?O 163 to 168°] and by three O—H?O hydrogen bonds [O?O 2.6589 (15) to 2.6775 (17) Å; O—H?O 165 to 177°] into a single three‐dimensional framework.     

Tetrameric triphenylsilanol, (Ph3SiOH)4, and the adduct (Ph3SiOH)2–di­methyl sulfoxide,both at 120 K,and the adduct (Ph3SiOH)4–1,4‐dioxan at 150 K: interplay of O—H⋯O and C—H⋯π(arene) interactions

The structure of tetrameric tri­phenyl­silanol, C₁₈H₁₆OSi, (I), has been re‐investigated at 120 (2) K. The hydroxyl H atoms were readily located and one of the arene rings is disordered over two closely positioned sets of sites. The mol­ecules are linked into cyclic tetramers, having approximate (S₄) symmetry, via O—H?O hydrogen bonds [H?O 1.81–1.85 Å, O?O 2.634 (3)–2.693 (3) Å and O—H?O 156–166°]. At ambient temperature, there are indications of multiple disorder of the phenyl‐ring sites. In bis­(tri­phenyl­silanol) di­methyl sulfoxide solvate, 2C₁₈H₁₆OSi·C₂H₆OS, (II), the di­methyl sulfoxide component is disordered across a twofold rotation axis in C2/c, and the molecular components are linked by a single O—H?O hydrogen bond [H?O 1.85 Å, O?O 2.732 (2) Å and O—H?O 172°] into three‐mol­ecule aggregates, which are themselves linked into a single three‐dimensional framework by two C—H?π(arene) interactions. In tetrakis­(tri­phenyl­silanol) 1,4‐dioxan solvate, 4C₁₈H₁₆OSi·C₄H₈O₂, (III), the 1,4‐dioxan component lies across an inversion centre in space group P and centrosymmetric five‐mol­ecule aggregates are linked by paired C—H?π(arene) interactions to form molecular ladders.     

2‐Amino‐4,6‐bis(benzyloxy)‐5‐nitrosopyrimidine: chains built from three‐centre N—H⋯(N,O) and N—H⋯π(arene) hydrogen bonds

The molecules of the title compound, C₁₈H₁₆N₄O₃, exhibit a very polarized molecular–electronic structure. The mol­ecules are linked into chains by a combination of an asymmetric three‐centre N—H?(N,O) hydrogen bond [H?N 2.19, H?O 2.54, N?N 3.041 (4) and N?O 2.977 (4) Å, and N—H?N 168, N—H?O 112 and N?H?O 67°] and an N—H?π(arene) interaction [H?Cg 2.67 Å, N?Cg 3.496 (4) Å and N—H?Cg 163°; Cg is a benzyl ring centroid].     

Chains of fused rings in the hydrogen‐bonded structure of meso‐­6,13‐di­amino‐6,13‐di­methyl‐1,4,8,11‐tetra­aza­cyclo­tetra­decane–2,2′‐biphenol (1/2)

The title compound is a salt, [C₁₂H₃₂N₆]²⁺·2[HOC₆H₄C₆H₄O]^?. The centrosymmetric cation contains two intramolecular N—H?N hydrogen bonds with an N?N distance of 2.8290 (13) Å, and the pendent amino groups are in axial sites; the anion contains an intramolecular O—H?O hydrogen bond with an O?O distance of 2.4656 (11) Å. The ions are linked into continuous chains by means of four types of N—H?O hydrogen bonds with N?O distances ranging from 2.7238 (12) Å to 3.3091 (13) Å, associated with N—H?O angles in the range 148–160°.     

N,N′‐Bis­[tris­(hydroxy­methyl)­methyl]­ethanedi­amide: six O—H⃛O hydrogen bonds generate only a two‐­dimensional structure

Molecules of the title compound, C₁₀H₂₀N₂O₈, adopt a conformation which is almost centrosymmetric. The mol­ecules are disordered over two sets of sites with an occupancy ratio of 0.94:0.06. In the major form, there are two intramolecular O—H?O hydrogen bonds [O?O 2.756 (4) and 2.765 (4) Å; O—H?O 144 and 146°], in which the two amidic O atoms act as acceptors. In addition, there are four intermolecular O—H?O hydrogen bonds [O?O 2.650 (3)–2.666 (3) Å; O—H?O 158–171°]; these link each mol­ecule to six others in a continuous sheet structure which contains five distinct ring motifs, two of the S(7) type, two of the R(10) type and one of the R(22) type.     

N,N′‐Di­methyl­piperazinium(2+) phos­phonoacetate: hydrogen‐bonded anion sheets containing cation‐templated R66(28) rings

In the title compound, C₆H₁₆N₂²⁺·2C₂H₄O₅P^?, the cations lie across centres of inversion; in the anions, two of the H‐atom sites have 0.50 occupancy. The anions are linked by short O—H?O hydrogen bonds [O?O 2.465 (3)–2.612 (3) Å and O—H?O 165–171°] into sheets of alternating R(12) and R(28) rings, both of which are centrosymmetric; the cations lie at the centres of the larger rings linked to the anion sheet by N—H?O hydrogen bonds [N?O 2.642 (2) Å and N—H?O 176°].