Solvated and solvent‐free forms of N,N′‐di­thio­diphthal­imide

N,N′‐Di­thio­diphthal­imide, C₁₆H₈N₂O₄S₂, crystallizes from ethyl acetate with two independent mol­ecules in the asymmetric unit, in which the N—S—S—N torsion angles are ?83.59 (19) and 92.9 (2)°. The mol­ecules are linked by C—H?O hydrogen bonds and aromatic π–π‐stacking interactions into a three‐dimensional framework. When crystallized from either di­chloro­methane or ethanol, solvates are formed in which the mol­ecules of the title compound lie across twofold rotation axes in space group C2/c, with N—S—S—N torsion angles of 93.54 (7) and 96.14 (11)°. There are no hydrogen bonds in these solvates, but the mol­ecules are linked by aromatic π–π‐stacking interactions into chains, between which there are continuous channels. Disordered solvent mol­ecules occupy these channels, which account for ca 20% of the unit‐cell volume.     

Bis(3‐nitro­phenyl) di­sulfide forms no C—H⃛O hydrogen bonds

In the title compound, C₁₂H₈N₂O₄S₂, the mol­ecules lie across twofold rotation axes in the space group C2/c. There are no intermolecular C—H?O hydrogen bonds, but the mol­ecules are linked into chains along [001] by aromatic π?π stacking interactions.     

Bis(4‐nitro­phenyl) di­sulfide at 150 K,a three‐dimensional framework built from C—H⋯O hydrogen bonds and aromatic π⋯π stacking interactions

In the title compound, (4‐O₂NC₆H₄)₂S₂ or C₁₂H₈N₂O₄S₂, the mol­ecules lie across twofold rotation axes. A single type of C—H?O hydrogen bond, with C?O = 3.394 (3) Å and C—H?O = 158°, links the mol­ecules into continuous two‐dimensional sheets built from a single type of R⁴₄(44) ring. These sheets are linked by aromatic π?π stacking interactions to form a continuous three‐dimensional framework.     

N,N′‐Di­thio­bisphthal­imide–nitro­benzene (2/1): a Pn solvate with localized solvent mol­ecules ordered head‐to‐tail in channels

N,N′‐Di­thio­bisphthal­imide crystallizes from nitro­benzene solution as a solvate, 2C₁₆H₈N₂O₄S₂·C₆H₅NO₂, having space group Pn. The bisphthal­imide mol­ecules are linked by C—H?O hydrogen bonds and by aromatic π–π‐stacking interactions, forming a framework enclosing continuous channels running along the [100] direction and accounting for ca 20% of the unit‐cell volume. The nitro­benzene mol­ecules lie in these channels, ordered in a head‐to‐tail fashion and linked to the bis­phthal­imide framework by C—H?O and C—H?π(arene) hydrogen bonds.     

catena‐Poly[[[tetra­aqua­zinc(II)]‐μ‐4,4′‐bipyridine] bis­(4‐hydroxy­benzene­sulfonate) trihydrate]

In the title compound, {[Zn(C₁₀H₈N₂)(H₂O)₄](C₆H₅O₄S)₂·3H₂O}_n, the Zn atom, the bipyridine ligand and one of water mol­ecules are located on twofold rotation axes. The Zn atom is coordinated by four O atoms from four water mol­ecules and two N atoms from two 4,4′‐bipyridine mol­ecules in a distorted octa­hedral geometry. The Zn²⁺ ions are linked by the 4,4′‐bipyridine mol­ecules to form a one‐dimensional straight chain propagating along the c axis. The 4‐hydroxy­benzene­sulfonate counter‐ions are bridged by the solvent water mol­ecules through hydrogen bonds to generate a two‐dimensional layer featuring large pores. In the crystal packing, the intra­layer pores form one‐dimensional channels along the c axis, in which the one‐dimensional [Zn(C₁₀H₈N₂)(H₂O)₄]²⁺ chains are encapsulated. Electrostatic inter­actions between cations and anions and extensive hydrogen bonds result in a three‐dimensional supra­molecular structure.     

1,1′‐Di(hydrazinocarbonylmethyl)‐2,2′‐biimidazole monohydrate and 1,1′‐di[2‐(hydrazinocarbonyl)ethyl]‐2,2′‐bi­imidazole

The crystal structures of the title compounds, alternatively called 2,2′‐(2,2′‐bi­imid­azole‐1,1′‐diyl)­diaceto­hydra­zide monohydrate, C₁₀H₁₄N₈O₂·H₂O, (I), and 3,3′‐(2,2′‐bi­imid­azole‐1,1′‐diyl)­dipropion­o­hydra­zide, C₁₂H₁₈N₈O₂, (II), respectively, have been determined. The mol­ecules consist of half‐mol­ecule asymmetric units related by a twofold rotation in (I) and by a center of inversion in (II). The imidazole rings of both mol­ecules crystallize in a nearly coplanar fashion [dihedral angles of 5.91 (3) and 0.0 (1)° for (I) and (II), respectively]. Both planar hy­dra­zinocarbonylalkyl substituents are essentially planar and assume the E orientation.     

l‐Me­thionyl‐l‐alanine–2‐propanol (1/2)

The crystal structure of the title compound, C₈H₁₆N₂O₃S·2C₃H₈O, is divided into hydro­phobic and hydro­philic layers. Two peptide mol­ecules in the asymmetric unit are related by pseudo‐translational symmetry along the a axis, as are two of the four 2‐propanol mol­ecules. The last two 2‐propanol mol­ecules in the asymmetric unit have different relative orientations and hydrogen‐bond interactions.     

1:1 Adduct of (S,S)‐4‐amino‐3,5‐bis­(1‐hydroxy­ethyl)‐1,2,4‐triazole with (S,S)‐1,2‐bis­(2‐hydroxy­propionyl)­hydrazine stabilized by eight hydrogen bonds

The structure of the cocrystallized 1:1 adduct of (S,S)‐4‐amino‐3,5‐bis­(1‐hydroxy­ethyl)‐1,2,4‐triazole and (S,S)‐1,2‐bis­(2‐hydroxy­propionyl)­hydrazine, C₆H₁₂N₄O₂·C₆H₁₂N₂O₄, has tetra­gonal symmetry. All eight O‐ and N‐bound H atoms are involved in inter­molecular hydrogen bonds, resulting in infinite zigzag chains of the triazole mol­ecules, with the hydrazine mol­ecules filling the gaps between the chains and completing a three‐dimensional hydrogen‐bonded array.     

The hydrogen‐bonded adduct 7,16‐diazonia‐18‐crown‐6–4‐aminobenzenesulfonate–water (1/2/2)

In the title hydrated adduct, 1,4,10,13‐tetraoxa‐7,16‐diazo­nia­cyclo­octa­decane bis(4‐amino­benzene­sulfonate) dihydrate, C₁₂H₂₈N₂O₄²⁺·2C₆H₆NO₃S⁻·2H₂O, formed between 7,16‐di­aza‐18‐crown‐6 and the dihydrate of 4‐amino­benzene­sulfonic acid, the macrocyclic cations lie across centres of inversion in the orthorhombic space group Pbca. The anions alone form zigzag chains, and the cations and anions together form sheets that are linked via water mol­ecules and anions to form a three‐dimensional grid.     

1,3‐Dibenzoylimidazolidine‐2‐thione and 1,3‐dibenzo­yl‐3,4,5,6‐tetra­hydro­pyrimidine‐2(1H)‐thione

The title compounds, 1,3‐dibenzo­ylimidazolidine‐2‐thione, C₁₇H₁₄N₂O₂S, (I), and 1,3‐dibenzo­yl‐3,4,5,6‐tetra­hydro­pyrimidine‐2(1H)‐thione, C₁₈H₁₆N₂O₂S, (II), were obtained from the reactions of imidazolidine‐2‐thione and 1,4,5,6‐tetra­hydro­pyrimidine‐2‐thiol, respectively, with benzoyl chloride. Compounds (I) and (II) contain, respectively, imidazolidinethione [C=S = 1.6509 (14) Å] and ­pyrimidinethione [C=S = 1.6918 (19) Å] moieties bonded to two benzoyl rings. The mol­ecules of (I) exhibit C₂ symmetry, the C=S bond lying along the twofold rotation axis, while the mol­ecules of (II) have mirror symmetry (C_s). The imida­zolidine ring in (I) is essentially planar, while the pyrimidine ring in (II) adopts a boat conformation. Mol­ecules of (I) are linked by weak inter­molecular C—H⋯O inter­actions, while mol­ecules of (II) are held together by van der Waals inter­actions.     

1,8,14,20‐Tetra­oxa‐11,23‐dithia­tricyclo­[21.3.0.09,13]hexa­cosa‐9,12,21,24‐tetra­ene

Mol­ecules of the title compound, C₂₀H₂₈O₄S₂, the first compound with a tetra­oxacyclo­hexa­cosane ring to be structurally characterized, lie on crystallographic centres of inversion, but have approximate C_2h mol­ecular symmetry. The parallel thio­phene rings are almost exactly planar; the overall conformation of the mol­ecule is chair‐like. The mol­ecules have voids that could, in principle, accommodate small guest mol­ecules, although in the crystal structure access to these voids is blocked by neighbouring mol­ecules.     

Hydrogen‐bonded sheets in the 1:1 cocrystal of biphenyl‐4,4′‐dicarboxylic acid with 2,5‐di‐4‐pyrid­yl‐1,3,4‐oxadiazole

The combination of biphenyl‐4,4′‐dicarboxylic acid (H₂bpa) and the bent dipyridyl base 2,5‐di‐4‐pyridyl‐1,3,4‐oxadiazole (4‐bpo) in a 1:1 molar ratio leads to the formation of the mol­ecular cocrystal (H₂bpa)·(4‐bpo) or C₁₄H₁₀O₄·C₁₂H₈N₄O. The asymmetric unit contains one‐half of an H₂bpa unit lying across a centre of inversion and one‐half of a 4‐bpo mol­ecule lying across a twofold rotation axis. Inter­molecular O—H⋯N inter­actions connect the acid and base mol­ecules to form a one‐dimensional zigzag chain. Through further weak C—H⋯O hydrogen bonds between adjacent chains, a two‐dimensional sheet‐like supramolecular network is afforded. As an extended analogue of terephthalic acid (H₂tp), the backbone geometry of H₂bpa has an evident influence on the hydrogen‐bonding pattern of the title cocrystal compared with that of (H₂tp)·(4‐bpo).     

N‐(4‐Cyano­phenyl)‐α‐(4‐methoxy­phenyl)­nitro­ne

In the crystal structure of the title compound, 4‐cyano‐N‐(4‐methoxy­benzyl­idene)­phenyl­amine N‐oxide, C₁₅H₁₂N₂O₂, the 4‐methoxy­phenyl is approximately coplanar with the nitrone moiety but significantly rotated with respect to the 4‐cyano­phenyl moiety. The extent of this rotation is significantly different for the two crystallographically independent mol­ecules of the asymmetric unit [dihedral angles of 19.4 (1) and 26.5 (1)°]. The geometry about the C=N bond is Z. The two mol­ecules are related to one another by a pseudo inversion centre.     

N,N′‐Bis(2‐pyridylmeth­yl)ferrocene‐1,1′‐diyldicarboxamide and N,N′‐bis­(3‐pyridylmeth­yl)ferrocene‐1,1′‐diyldicarboxamide

The mol­ecules of N,N′‐bis­(2‐pyridylmeth­yl)ferrocene‐1,1′‐diyl­dicarboxamide, [Fe(C₁₂H₁₁N₂O)₂], contain intra­molecular N—H⋯N hydrogen bonds and are linked into sheets by three independent C—H⋯O hydrogen bonds. The mol­ecules of the isomeric compound N,N′‐bis­(3‐pyridylmeth­yl)ferrocene‐1,1′‐diyldicarboxamide lie across inversion centres, and the mol­ecules are linked into sheets by a combination of N—H⋯N hydrogen bonds and π–π stacking inter­actions between pyridyl groups.     

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.     

μ‐3,4′‐Bi‐1,2,4‐triazole‐di‐μ‐chloro‐cuivre(II) monohydraté

In the title compound, μ‐3,4′‐bi‐1,2,4‐triazole‐di‐μ‐chloro‐copper(II) monohydrate, {[CuCl₂(C₄H₄N₆)]·H₂O}_n, the Cu atom is located in a distorted octahedron consisting of two N atoms and four Cl atoms. The structural unit is an infinite chain in which octahedral groups, connected by shared edges, are also linked by bitriazole mol­ecules. The bitriazole ligand, the Cu atom and the water O atom all lie on independent twofold axes. The structure is held together by hydrogen bonds between the water mol­ecules and the non‐coordinated N atoms of the ligand, and by van der Waals forces.     

Poly­[[[aqua­manganese(II)]‐μ2‐4,4′‐bi­pyridine‐μ3‐succinato] 4,4′‐bi­pyridine hemisolvate]

The polymeric title complex, {[Mn(C₄H₄O₄)(C₁₀H₈N₂)(H₂O)]·0.5C₁₀H₈N₂}_n, possesses a three‐dimensional open‐framework structure, with the solvate 4,4′‐bi­pyridine (bipy) mol­ecules, which lie around centers of inversion, clathrated in the channels of the framework. The Mn^II center is surrounded by three succinate (succ) ligands, one water mol­ecule and two bipy ligands, and displays a slightly distorted octahedral coordination environment, with cis angles ranging from 84.14 (12) to 96.56 (11)°. Each succ dianion coordinates to three Mn^II atoms, thus acting as a bridging tridentate ligand; in turn, the Mn^II atoms are bridged by three succ ligands, thus forming a two‐dimensional Mn–succ sheet pillared by the bridging bipy ligands. Two hydrogen‐bonding interactions, involving the water mol­ecules and the carboxy O atoms of the succ ligands, are present in the crystal structure.     

A two‐dimensional network of R(16) and R(8) rings in trans‐bis(4‐amino­pyridine‐κN1)­bis­(benzoato‐κ2O,O′)­copper(II) benzene 0.75‐solvate

The structure of the title supramolecular complex, [Cu(C₇H₅O₂)₂(C₅H₆N₂)₂]·0.75C₆H₆, has been determined. The Cu²⁺ ion lies on an inversion centre and is coordinated by four O atoms of two opposing benzoate mol­ecules and two pyridine N atoms of two opposing amino­pyridine mol­ecules. The partially occupied benzene site lies across a twofold rotation axis. The crystal structure is dominated by two‐dimensional networks containing two different hydrogen‐bonded rings [(16) and (8)].     

N‐(2‐Amino‐1,6‐di­hydro‐5‐nitro­so‐6‐oxopyrimidin‐4‐yl)‐l‐isoleucine–water (4/1): interplay of molecular and supramolecular structures

In the title compound, 2C₁₀H₁₅N₅O₄·0.5H₂O, there are two independent mol­ecules of the pyrimidinyl­isoleucine in general positions and a water mol­ecule lying on a twofold rotation axis. The bond lengths within the organic moieties demonstrate significant polarization of the electronic structure. Each of the organic mol­ecules participates in 12 intermolecular hydrogen bonds, of O—H?O and N—H?O types, while the water mol­ecule acts as a double donor and as a double acceptor of O—H?O hydrogen bonds. The organic components are linked by the hydrogen bonds into a single three‐dimensional framework, reinforced by the water mol­ecules.     

A series of three bis­[2‐(methyl/tri­fluoro­methyl)‐4H‐3,1‐benzoxazin‐4‐one] compounds

Each of the three title compounds, namely 6,6′‐methyl­ene­bis­(2‐methyl‐4H‐3,1‐benz­oxazin‐4‐one), C₁₉H₁₄N₂O₄, 6,6′‐methyl­ene­bis­(2‐tri­fluoro­methyl‐4H‐3,1‐benz­oxazin‐4‐one), C₁₉H₈F₃N₂O₄, and 6,6′‐bi­(2‐tri­fluoro­methyl‐4H‐3,1‐benz­oxazin‐4‐one), C₁₈H₆F₆N₂O₄, contains two planar benz­ox­azin­one fragments. In the first two compounds, these planes are virtually perpendicular to each other, while the third compound is planar overall. The electronic effects of the substituent groups on the oxazine moiety result in distortion of the bond angles at the C atoms of the C=O and C=N bonds, and in redistribution of electronic density in the oxazine rings. The latter leads to different bond lengths within this ring in the three mol­ecules. All the mol­ecules form stacks in their crystals with distances of 3.2–3.6 Å between adjacent mol­ecules in a stack.