2′‐(4‐Fluoro­phenyl)‐[1,2,3]­triazolo[4′,5′:16,17]­androst‐5‐en‐3β‐ol methanol hemisolvate

The asymmetric unit of the title compound, C₂₅H₃₀FN₃O·0.5CH₃OH, contains four symmetry‐independent steroid and two methanol mol­ecules. The conformations of the independent steroid mol­ecules are very similar. Intermolecular O—H⋯O hydrogen bonds create two independent chains, each of which links two of the independent steroid mol­ecules plus one methanol mol­ecule via a co‐operative O—H⋯O—H⋯O—H pattern. Intermolecular C—H⋯O and C—H⋯F interactions are also observed.     

4‐Amino‐5‐(2‐hydroxy‐4,4‐di­methyl‐6‐oxo­cyclo­hexenyl­methyl)‐1‐methyl‐2‐(methyl­sulfanyl)­pyrimidin‐6(1H)‐one: hydrogen‐bonded chains are π‐stacked in pairs

Molecules of the title compound, C₁₅H₂₁N₃O₃S, have a markedly polarized electronic structure; the carbocyclic ring adopts an envelope conformation and the overall molecular conformation appears to be controlled by two intramolecular hydrogen bonds, one each of the O—H⋯O and N—H⋯O types. The mol­ecules are linked into C(6) chains by an intermol­ecular N—H⋯O hydrogen bond, and pairs of these hydrogen‐bonded chains are linked by a π–π stacking interaction.     

Dimorphism in (2Z)‐2‐benzyl­idene‐N,7‐dimethyl‐3‐oxo‐5‐phenyl‐2,3‐dihydro‐5H‐1,3‐thia­zolo[3,2‐a]pyrimidine‐6‐carboxamide

The title compound, C₂₂H₁₉N₃O₂S, crystallizes in two polymorphic forms having the same space group, viz. P, with Z′ = 2 and Z′ = 1. In both polymorphs, the planar thia­zole ring is fused cis with the dihydro­pyrimidine ring, the carbamoyl group is in an extended conformation with an anti­clinal orientation with respect to the pyrimidine ring, and the phenyl ring is attached to the pyrimidine ring approximately at a right angle. The two polymorphs have different inter­planar angles between the phenyl and thia­zole rings. The mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds.     

N‐(3H‐Thia­zol‐2‐yl­idene)­nitr­amine and N‐methyl‐N‐(thia­zol‐2‐yl)­nitr­amine

The geometries of the thia­zole ring and the nitr­amino groups in N‐(3H‐thia­zol‐2‐yl­idene)­nitr­amine, C₃H₃N₃O₂S, (I), and N‐­methyl‐N‐(thia­zol‐2‐yl)­nitr­amine, C₄H₅N₃O₂S, (II), are very similar. The nitr­amine group in (II) is planar and twisted along the C—N bond with respect to the thia­zole ring. In both structures, the asymmetric unit includes two practically equal mol­ecules. In (I), the mol­ecules are arranged in layers connected to each other by N—H⋯N and much weaker C—H⋯O hydrogen bonds. In the crystal structure of (II), the mol­ecules are arranged in layers bound to each other by both weak C—H⋯O hydrogen bonds and S⋯O dipolar interactions.     

4‐(4‐Fluoro‐3‐phenoxy­phen­yl)‐6‐(4‐fluoro­phen­yl)‐2‐oxo‐1,2‐dihydro­pyridine‐3‐carbonitrile and the 6‐(4‐methyl­phen­yl)‐ analogue

The crystal structures of the title compounds, viz. C₂₄H₁₄F₂N₂O₂, (I), and C₂₅H₁₇FN₂O₂, (II), respectively, have been determined in order to unravel the role of an ordered F atom in generating stable supra­molecular assemblies. On changing the substitution from fluorine to a methyl group, C—H⋯F inter­actions are replaced by C—H⋯π inter­actions, revealing the importance of such weak inter­actions when present alongside N—H⋯O and C—H⋯O hydrogen bonds. The dihedral angle between the planes of the 4‐fluoro­phenyl ring and the pyridine ring is 26.8 (1)° in (I), while that between the planes of the 4‐methyl­phenyl and pyridine rings is 29.5 (1)° in (II).     

1‐Methyl‐1‐phenyl‐3‐[1‐hydroxy­imino‐2‐(succinimido)­ethyl]­cyclo­butane

In the title compound, C₁₇H₂₀N₂O₃, the cyclo­butane ring is puckered, with a dihedral angle of 19.11 (15)°. The 1‐phenyl and 3‐[1‐hydroxy­imino‐2‐(succinimido)­ethyl] groups are in cis positions. The mol­ecules are linked by O—H⋯O and C—H⋯π(benzene) interactions, forming a two‐dimensional network.     

Bis(μ‐acetato)(μ‐2,6‐bis­{[(2‐hydroxy­ethyl)(2‐pyridylmeth­yl)amino]meth­yl}‐4‐methyl­phenolato)dinickel(II) hexa­fluoro­phosphate hemihydrate

The asymmetric unit of the title compound, [Ni₂(C₂₅H₃₁N₄O₃)(C₂H₃O₂)₂]PF₆·0.5H₂O, consists of two dinuclear nickel cations, two hexa­fluoro­phosphate anions and one water mol­ecule of crystallization. Within each cation, the Ni atoms are bridged by two exogenous acetate groups and an endogenous cresol O atom of a phenolate‐based `end‐off' compartmental ligand that possesses two pendant chelating arms attached to the ortho positions of the phenol ring. Each Ni atom is six‐coordinate with a slightly distorted octa­hedral geometry. The two symmetry‐independent cations are linked into a dimeric unit through O—H⋯O hydrogen bonds. Additional O—H⋯O, C—H⋯F and C—H⋯O inter­molecular inter­actions link all of the units in the structure into a three‐dimensional framework.     

Ethyl (E)‐3‐(2‐hydroxy­phenyl)‐2‐(morpholino­carbonyl)­propenoate

The title compound, C₁₆H₁₉NO₅, crystallizes as a centrosymmetric dimer through strong O—H⋯O hydrogen‐bonding interactions between the hydroxy­phenyl and morpholino­carbonyl groups. The morpholino­carbonyl group is almost perpendicular to the propenoate moiety. Electron delocalization in the N—C(=O) fragment leads to the formation of hydrogen‐bonded S(5) ring motifs through C—H⋯O interactions.     

C—H⋯O,C—H⋯π and π–π inter­actions in three benzofuran‐2‐yl ketone derivatives

The mol­ecules of 2‐benzoyl‐1‐benzofuran, C₁₅H₁₀O₂, (I), inter­act through double C—H⋯O hydrogen bonds, forming dimers that are further linked by C—H⋯O, C—H⋯π and π–π inter­actions, resulting in a three‐dimensional supramolecular network. The dihedral angle between the benzo­yl and benzofuran fragments in (I) is 46.15 (3)°. The mol­ecules of bis­(5‐bromo‐1‐benzofuran‐2‐yl) ketone, C₁₇H₈Br₂O₃, (II), exhibit C₂ symmetry, with the carbon­yl group (C=O) lying along the twofold rotation axis, and are linked by a combination of C—H⋯O and C—H⋯π inter­actions and Br⋯Br contacts to form sheets. The stability of the mol­ecular packing in 3‐mesit­yl‐3‐methyl­cyclo­but­yl 3‐methyl­naphtho[1,2‐b]furan‐2‐yl ketone, C₂₈H₂₈O₂, (III), arises from C—H⋯π and π–π stacking inter­actions. The fused naphthofuran moiety in (III) is essentially planar and makes a dihedral angle of 81.61 (3)° with the mean plane of the trimethyl­benzene ring.     

1‐Acetyl‐3‐ferrocenyl‐5‐methyl‐1H‐pyrazole and 1‐acetyl‐5‐ferrocenyl‐3‐(2‐pyrid­yl)‐1H‐pyrazole

Mol­ecules of 1‐acetyl‐3‐ferrocenyl‐5‐methyl‐1H‐pyrazole, [Fe(C₅H₅)(C₁₁H₁₁N₂O)], form a centrosymmetric dimer generated by a combination of one C—H⋯π(pyrazole) and one C—H⋯π(cyclo­penta­dienyl) inter­action. The dimers are linked by C—H⋯π inter­actions, involving the pyrazole rings as acceptors, into layers parallel to (10). Mol­ecules of 1‐acetyl‐5‐ferrocenyl‐3‐(2‐pyrid­yl)‐1H‐pyrazole, [Fe(C₅H₅)(C₁₅H₁₂N₃O)], are linked by C—H⋯O inter­actions into a chain running in the [010] direction. Two chains of this type passing through each unit cell are connected by O⋯π(pyridyl) inter­actions into an [010] double chain.     

ent‐7α,18‐Hydroxy­kaur‐16‐ene ethanol solvate

The ent‐kaurene diterpene in the title compound, 7‐epican­dicandiol ethanol solvate, C₂₀H₃₂O₂·C₂H₆O, was isolated from the aerial parts of Sideritis ozturkii Aytaç & Aksoy. The mol­ecule has the usual conformation and stereochemistry found in related ent‐kaurene derivatives. The methyl‐substituted ring junction has a trans arrangement and the other junction is cis. The six‐membered rings have chair or slightly distorted chair conformations and the five‐membered ring has an envelope conformation. Inter­molecular hydrogen bonds link the 7‐epicandicandiol and ethanol mol­ecules into two‐dimensional networks, part of which comprise co‐operative O—H⋯O—H⋯O—H⋯ chains.     

Ferrocene compounds. XXXIV. 1′‐(tert‐Butoxycarbonylamino)ferrocene‐1‐carboxylic acid

Heteroannularly substituted ferrocene derivatives can act as model systems for various hydrogen‐bonded assemblies of biomol­ecules formed, for instance, by means of O—H⋯O and N—H⋯O hydrogen bonding. The crystal structure analysis of 1′‐(tert‐butoxy­carbonyl­amino)­ferrocene‐1‐carbox­ylic acid, [Fe(C₁₀H₁₄NO₂)(C₆H₅O₂)] or (C₅H₄COOH)Fe(C₅­H₄NHCOOC(CH₃)₃, reveals two independent mol­ecules within the asymmetric unit, and these are joined into discrete dimers by two types of intermolecular hydrogen bonds, viz. O—H⋯O and N—H⋯O. The –COOH and –NHCOOR groups are archetypes for dimer formation via two eight‐membered rings. The O—H⋯O hydrogen bonds [2.656 (3) and 2.663 (3) Å] form a cyclic carboxylic acid dimer motif. Another eight‐membered ring is formed by N—H⋯O hydrogen bonds [2.827 (3) and 2.854 (3) Å] between the N—H group and an O atom of another carbamoyl moiety. The dimers are assembled in a herring‐bone fashion in the bc plane.     

4,4,6,6‐Tetra­chloro‐2,2‐(ethyl­ene­di­oxy­di‐o‐phenyl­enedi­imino)‐2λ5,4λ5,6λ5‐cyclo­triphosphazene

The title ligand, C₁₄H₁₄Cl₄N₅O₂P₃, is a cyclo­phosphazene lariat (PNP pivot) ether with a spiro‐cyclic 11‐membered macrocyclic ring containing two ether O and two N atoms; the phosphazene ring is nearly planar. The macrocyclic ring contains a four‐centred (trifurcate) N—H⋯O/N—H⋯N hydrogen bond, and the relative inner‐hole size of the macrocycle is ∼1.14 Å in radius. The mol­ecules are linked about inversion centres by N—H⋯N hydrogen bonds into centrosymmetric dimers.     

4,4′‐Butane‐1,4‐diylbis[3‐ethyl‐1H‐1,2,4‐triazol‐5(4H)‐one] and 4‐hydr­oxy‐3‐n‐prop­yl‐1H‐1,2,4‐triazol‐5(4H)‐one

The title compounds, C₁₂H₂₀N₆O₂, (I), and C₅H₉N₃O₂, (II), display the characteristic features of 1,2,4‐triazole derivatives. Compound (I) lies about an inversion centre which is at the mid‐point of the central C—C bond. Compound (II) also contains a planar 1,2,4‐triazole ring but differs from (I) in that it has a hydr­oxy group attached to the ring. Mol­ecules of (I) are held together in the crystal structure by inter­molecular N—H⋯O contacts and by weak π–π stacking inter­actions between the 1,2,4‐triazole moieties. Compound (II) contains inter­molecular O—H⋯O and N—H⋯O hydrogen bonds.     

Ethyl 3‐amino‐6‐phenyl‐4‐tolylthieno[2,3‐b]pyridine‐2‐carboxylate

In the title compound, C₂₃H₂₀N₂O₂S, the central thieno­pyridine ring system is essentially planar, the dihedral angle between the planes of the two rings being 0.3 (2)°. The terminal ethyl carboxyl­ate group is twisted by 26.7 (3)° away from the central ring system. A short intramolecular hydrogen bond involving the amino N atom and the carbonyl O atom [N⋯O = 2.806 (4) Å] forms a pseudo‐six‐membered ring. Significant intermolecular C—H⋯N, C—H⋯O and C—H⋯π interactions contribute strongly to the stability of the structure, along with weak π–π‐stacking interactions.     

N‐Cyclo­hexyl‐2‐[5‐(4‐pyridyl)‐4‐(p‐tolyl)‐4H‐1,2,4‐triazol‐3‐yl­sulfanyl]­acetamide dihydrate

In the title compound, C₂₂H₂₅N₅OS·2H₂O, the mol­ecules are stacked in columns running along the b axis. In this arrangemant, the mol­ecules are linked to each other by a combination of one two‐centre N—H⋯O hydrogen bond and four two‐centre O—H⋯O hydrogen bonds containing two types of ring motif, viz.R₄⁴(10) and R₃³(11). In the crystal structure, centrosymmetric π–π inter­actions between the triazole rings, with a distance of 3.691 (2) Å between the ring centroids, also affect the packing of the mol­ecules.     

N1‐(4‐tert‐Butyl­phenyl)‐N2‐hydroxy‐α‐oxo‐α‐phenyl­acet­amidine and N2‐hydroxy‐N1‐(4‐nitro­phenyl)‐α‐oxo‐α‐phenyl­acet­amidine hemihydrate

In the title compounds, C₁₈H₂₀N₂O₂, (I), and C₁₄H₁₁N₃O₄·0.5H₂O, (II), respectively, the oxime groups have an E configuration. In (I), the mol­ecules exist as polymers bound by intermolecular C—H⋯O and O—H⋯N hydrogen bonds around inversion centres. In (II), intermolecular OW—H⋯N, OW—H⋯O and O—H⋯OW interactions stabilize the molecular packing.     

Salicylaldehyde 4,4′‐(hexane‐1,6‐di­yl)­thio­semicarbazone

The title compound, C₁₄H₁₉N₃OS, is in the thio­keto form, with the thione S and hydrazine N atoms cis with respect to each other so that the S atom is involved in inter‐ and intra­molecular hydrogen bonds simultaneously. Inter­molecular C—H⋯S and C—H⋯O hydrogen bonds result in one‐dimensional polymeric chains of mol­ecules along the a axis. A weak C—H⋯π ring inter­action binds the polymeric chains together.     

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.     

2,3‐Difluoro‐4‐formyl­phenyl­boronic acid

The mol­ecule of the title compound, 2,3‐F₂‐4‐(CHO)C₆H₂B(OH)₂ or C₇H₅BF₂O₃, contains a formyl group coplanar with the benzene ring. The boronic acid group is twisted with respect to the benzene ring plane. The mol­ecules are organized into infinite chains via inter­molecular O—H⋯O hydrogen bonds. These chains are additionally connected via strong O—H⋯O hydrogen bonds, producing a folded layer structure perpendicular to the a axis. These layers are paired due to B⋯F inter­actions.