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.     

trans‐[1,3‐Bis(2,4‐di­methyl­phenyl)­imidazolidin‐2‐yl­idene]­di­chloro­(tri­phenyl­phosphine‐κP)­palladium(II)

The title complex, [PdCl₂(C₁₉H₂₂N₂)(C₁₈H₁₅P)], shows slightly distorted square‐planar coordination of the palladium(II) metal center. The Pd—C bond distance between the N‐heterocyclic ligand and the metal atom is 2.008 (3) Å. The dihedral angle between the two di­methyl­phenyl ring planes is 33.17 (13)°.     

2‐Benzoyl‐N‐phenyl‐2‐(1,2,4‐triazol‐1‐yl)­thio­acet­amide and 2‐(4‐methoxy­benzoyl)‐N‐phenyl‐2‐(1,2,4‐triazol‐1‐yl)­thio­acet­amide

In the two title compounds, C₁₇H₁₄N₄OS, (I), and C₁₈H₁₆N₄O₂S, (II), the dihedral angles between the planes of the triazole and N‐phenyl rings and the plane of five of the atoms that link these two rings are 63.5 (8) and 73.2 (6)° for (I), and 65.1 (1) and 72.1 (3)° for (II), respectively. There are some inter‐ and intramolecular interactions in the crystal structure.     

3‐(4‐Chloro­benzoyl)‐7‐(N,N‐di­methyl­amino)‐1‐phenyl­indolizine and 3‐(2,4‐di­chloro­benzoyl)‐7‐(N,N‐di­methyl­amino)‐1‐phenyl­indolizine

In both of the title compounds, C₂₃H₁₉ClN₂O, (I), and C₂₃H₁₈Cl₂N₂O, (II), the molecular packing is influenced by weak intermolecular C—H⋯O and C—H⋯π interactions, but despite the chemical similarity of the compounds, the packing in (II) is entirely different from that observed in (I).     

1,3‐Bis(4‐methyl­phen­yl)triazene, 1‐(4‐chloro­phen­yl)‐3‐(4‐fluoro­phen­yl)triazene and 1‐(4‐fluoro­phen­yl)‐3‐(4‐methyl­phen­yl)triazene

The title 4,4′‐disubstituted diphen­yl‐1,3‐triazines, C₁₄H₁₅N₃, (I), C₁₂H₉ClFN₃, (II), and C₁₃H₁₂FN₃, (III), each contain a triazene group (–N=N—NH–) having an extended conformation. The dihedral angles between the two benzene rings in (I), (II) and (III) are 4.3, 3.4 and 6.5°, respectively. The mol­ecules are almost entirely planar, with maximum deviations from the mean planes of 0.1087 (2), −0.1072 (7) and 0.1401 (3) Å, respectively. In each compound, the molecules are linked by N—H⋯N hydrogen bonds to form chains and pack similarly in the crystal structures.     

1,2‐Di­cyano‐1,2‐bis­(imidazolidine‐2‐thione)­digold(I) and 2,2‐di­cyano‐1,1‐bis­(di­methyl­thio­urea)­digold(I)

Gold(I) cyanide forms complexes with imidazolidine‐2‐thione (etu) and di­methyl­thio­urea (dmtu) with the formula [Au₂(CN)₂L₂], i.e. the title complexes di­cyano‐1κC,2κC‐bis(imidazolidine‐2‐thione)‐1κS,2κS‐digold(I)(Au—Au), [Au₂(CN)₂(C₃H₆N₂S)₂], and di­cyano‐1κ²C‐bis(N,N′‐di­methyl­thio­urea)‐2κ²S‐digold(I)(Au—Au), [Au₂(CN)₂(C₃H₈N₂S)₂]. In the etu complex, two approximately linear (etu)AuCN groups are held together by a weak homopolar Au—Au bond [3.117 (1) Å], with a torsion angle of 61 (3)° between the two groups. In the dmtu complex, an approximately linear Au(dmtu)₂ group is bound to an approximately linear Au(CN)₂ group by a weak heteropolar Au—Au bond [3.091 (1) Å], with a torsion angle of 83 (5)° between the two groups.     

5‐Acetyl‐2‐amino‐6‐methyl‐4‐(3‐nitrophenyl)‐4H‐pyran‐3‐carbonitrile and 2‐amino‐5‐ethoxycarbonyl‐6‐methyl‐4‐(3‐nitrophenyl)‐4H‐pyrano‐3‐carbonitrile

The structures of the title compounds, C₁₅H₁₃N₃O₄, (I), and C₁₆H₁₅N₃O₅ [IUPAC name: ethyl 6‐amino‐5‐cyano‐2‐methyl‐4‐(3‐nitro­phenyl)‐4H‐pyrano‐3‐carboxyl­ate], (II), are very similar, with the heterocyclic rings adopting boat conformations. The pseudo‐axial m‐nitro­phenyl substituents are rotated by 84.0 (1) and 98.7 (1)° in (I) and (II), respectively, with respect to the four coplanar atoms of the boat. The dihedral angles between the phenyl rings and nitro groups are 12.1 (2) and 8.4 (2)° in (I) and (II), respectively. The two compounds have similar patterns of intermolecular N—H?O and N—H?N hydrogen bonding, which link mol­ecules into infinite tapes along b .     

Charge‐transfer complexes of 4‐(di­methyl­amino)­pyridine with 2,4‐, 3,4‐ and 3,5‐di­nitro­benzoic acid

In the three title crystal structures 4‐(di­methyl­amino)­pyridinium 2,4‐di­nitro­benzoate, (I), 4‐(di­methyl­amino)­pyri­dinium 3,4‐di­nitro­benzo­ate, (II), and 4‐(di­methyl­amino)pyri­din­ium 3,5‐di­nitro­benzo­ate, (III), all C₇H₁₁N₂⁺·C₇H₃N₂O₆^?, the ions are connected by an N—H?O hydrogen bond. Dihedral angles between the pyridine and phenyl rings are 69.9 (1), 26.7 (1) and 56.2 (1)° in (I), (II) and (III), respectively. Donor–acceptor π–π stacking is observed in (II) and (III), but not in (I).     

3‐(2‐Furyl)‐6‐(4‐methyl­phenyl)‐7H‐1,2,4‐triazolo­[3,4‐b][1,3,4]thia­diazine and its 6‐phenyl analogue

In the title compounds, C₁₅H₁₂N₄OS, (I), and C₁₄H₁₀N₄OS, (II), the thia­diazine ring adopts a skew‐boat conformation, while the triazole and furyl rings are essentially planar. The phenyl group is twisted by 33.5 (2) and 47.9 (1)° out of the triazole‐ring plane in (I) and (II), respectively.     

(Z)‐3‐(1H‐Indol‐3‐yl)‐2‐(3‐thienyl)­acrylo­nitrile and (Z)‐3‐[1‐(4‐tert‐butyl­benzyl)‐1H‐indol‐3‐yl]‐2‐(3‐thienyl)­acrylo­nitrile

(Z)‐3‐(1H‐Indol‐3‐yl)‐2‐(3‐thienyl)­acrylo­nitrile, C₁₅H₁₀N₂S, (I), and (Z)‐3‐[1‐(4‐tert‐butyl­benzyl)‐1H‐indol‐3‐yl]‐2‐(3‐thienyl)­acrylo­nitrile, C₂₆H₂₄N₂S, (II), were prepared by base‐catalyzed reactions of the corresponding indole‐3‐carbox­aldehyde with thio­phene‐3‐aceto­nitrile. ¹H/¹³C NMR spectral data and X‐ray crystal structures of compounds (I) and (II) are presented. The olefinic bond connecting the indole and thio­phene moieties has Z geometry in both cases, and the mol­ecules crystallize in space groups P2₁/c and C2/c for (I) and (II), respectively. Slight thienyl ring‐flip disorder (ca 5.6%) was observed and modeled for (I).     

Two rhod­amine derivatives: 9‐[2‐(ethoxycarbonyl)phenyl]‐3,6‐bis(ethyl­amino)‐2,7‐di­methyl­xanthyl­ium chloride monohydrate and 3,6‐di­amino‐9‐[2‐(methoxy­carbonyl)­phenyl]xanthyl­ium chloride trihydrate

The title compounds, C₂₈H₃₁N₂O₃⁺·Cl^?·H₂O (common name rhod­amine‐6g), (I), and C₂₁H₁₇N₂O₃⁺·Cl^?·3H₂O (common name rhod­amine‐123), (II), both have planar xanthene skeletons with a formal +1 charge on the amino N atoms delocalized through the π‐electron system so that the N—Csp² bond distances indicate significant double‐bond character. The substituted planar phenyl groups make angles of 63.29 (8) and 87.96 (11)° with the xanthene planes in (I) and (II), respectively. In both mol­ecules, the carbonyl bond vectors point toward the xanthene rings. The ethyl­amine groups in (I) are oriented similarly with their CH₂–CH₃ bond vectors pointing nearly perpendicular to the xanthene plane. The chloride ions and water mol­ecules are disordered in both structures. In (I), the chloride ion and water mol­ecule are disordered between two sites. One water and chloride alternately occupy the same site with occupancy factors of 0.5. The other 0.5‐chloride and 0.5‐water occupy two distinct positions separated by 0.747 (8) Å. In (II), the chloride ion is disordered between three sites and one of the waters is disordered about two other sites. Both crystal structures are stabilized by hydrogen bonds involving the chloride ions, amino groups and water mol­ecules, as well as by π–π stacking between xanthene planes.     

2‐[(E)‐(4‐Chloro­phenyl)­methyl­ene­amino]‐N‐(X‐methyl­phenyl)‐4,5,6,7‐tetra­hydro‐1‐benzo­thio­phene‐3‐carbox­amide,where X = 2 and 3

The title compounds, both C₂₃H₂₁ClN₂OS, are isomeric, with (I) and (II) being the N‐3‐methyl­phenyl and N‐2‐methyl­phenyl derivatives, respectively. The dihedral angle between the 4‐chloro­phenyl group and the thio­phene ring in (II) [38.1 (1)°] is larger than that in (I) [7.1 (1)°], indicating steric repulsion between the chloro­phenyl and o‐toluidine groups in (II). In both compounds, an intramolecular N—H⋯N hydrogen bond forms a pseudo‐six‐membered ring, thus locking the molecular conformation. In the crystal structures, mol­ecules are connected via N—H⋯O hydrogen bonds, forming chains along the b axis in (I) and along the c axis in (II). Intermolecular C—H⋯O/S and π–π interactions are also observed in (II), but not in (I).     

A hydrogen‐bonded chain of rings in 5‐amino‐1‐(4‐methoxybenzoyl)‐3‐methylpyrazole and a three‐dimensional hydrogen‐bonded framework in 5‐amino‐3‐methyl‐1‐(2‐nitrobenzoyl)pyrazole

The molecules of 5‐amino‐1‐(4‐methoxybenzoyl)‐3‐methylpyrazole, C₁₂H₁₃N₃O₂, (I), and 5‐amino‐3‐methyl‐1‐(2‐nitrobenzoyl)pyrazole, C₁₁H₁₀N₄O₃, (II), both contain intramolecular N—H...O hydrogen bonds. The molecules of (I) are linked into a chain of rings by a combination of N—H...N and N—H...π(arene) hydrogen bonds, while those of (II) are linked into a three‐dimensional framework structure by N—H...N and C—H...O hydrogen bonds.     

Bis­(di‐μ‐acetato‐aqua{2‐[N‐ethyl‐N‐(2‐hydroxy‐4‐methyl­benzyl)­amino­methyl]‐1‐methyl­benz­imid­az­ole}­nickel)­nickel(II) tetra­hy­drate

The previously unknown title compound, tetra‐μ‐ace­tato‐1:2κ²O;1:2κ²O:O′;­2:3κ²O;­2:3κ²O:O′‐di­aqua‐1κO,3κO‐bis­(μ‐2‐{[N‐ethyl‐N‐(2‐hy­droxy‐5‐methylbenzyl)­am­ino]­methyl}‐1‐methyl‐1H‐benz­imid­az­ole)‐1κ³N³,N,O:2κO;3κ³N³,N,O:2κO‐tri­nickel(II) tetra­hy­drate, [Ni₃(C₁₈H₂₂N₃O)₂(C₂H₃O₂)₄(H₂O)₂]·­4H₂O, (I), is a centrosymmetric linear trinuclear nickel(II) complex, where the Ni atoms are in an octahedral coordination and the ligand heteroatoms act so as to model amino acid residues.     

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.     

Chloro­di­methyl(N‐methyl­pyrrolidin­one)­tin(IV)‐μ‐chloro‐di­chloro­di­methyl­tin(IV)

The synthesis and the X‐ray structural analysis of the title compound, μ‐chloro‐1:2κ²Cl‐tri­chloro‐1κCl,2κ²Cl‐tetra­methyl‐1κ²C,2κ²C‐(N‐methyl­pyrrolidin‐2‐one)‐1κO‐ditin(IV), [Sn₂Cl₄(CH₃)₄(C₅H₉NO)], are described. The title compound is found to exhibit a distorted trigonal–bipyramidal geometry at both Sn^IV atoms. The Sn—Cl—Sn angle involving the bridging chlorine ligand is 135.56 (5)°, with the Sn—Cl bond lengths being 2.5704 (13) and 3.1159 (13) Å.     

N‐Benzyl‐N‐(2‐methoxy­phenyl)­cyclo­hex‐1‐ene­carbox­amide

The title amide, C₂₁H₂₃NO₂, (I), does not photocyclize in the solid state. The methoxy group is involved in intermolecular steric interactions and so prevents the rotation of the N‐phenyl group in the crystal.     

(E)‐4‐(4‐Bromo­phenyl­diazen­yl)‐2,6‐dimethyl­phenyl acrylate and (E)‐2,6‐dimethyl‐4‐(4‐methyl­phenyl­diazen­yl)­phenyl acrylate

The crystal structures of the title compounds, C₁₇H₁₅BrN₂O₂, (I), and C₁₈H₁₈N₂O₂, (II), determined at room temperature, have a trans configuration with respect to the diazene linkage, as found for other azo (diazene) derivatives. The aromatic mean planes are nearly coplanar, with a dihedral angle between these planes of 8.31 (2)° for (I) and 3.74 (2)° for (II). In both complexes, the mean plane of the ester group is nearly perpendicular to the aromatic ring planes. In both compounds, the crystal packing involves only π–π and π–ring inter­actions, which combine to stabilize the extended structure.     

Bis­(saccharinato‐κN)zinc(II) com­plexes with N,N′‐bidentate 2‐amino­methyl­pyridine and 2‐amino­ethylpyridine

The structures of trans‐bis[2‐(amino­methyl)­pyridine‐κ²N,N′]­bis­(saccharinato‐κN)­zinc(II), [Zn(C₇H₄NO₃S)₂(C₆H₈N₂)₂], (I), and [2‐(amino­ethyl)­pyridine‐κ²N,N′]bis­(saccharinato‐κN)­zinc(II), [Zn(C₇H₄NO₃S)₂(C₇H₁₀N₂)], (II), exhibit octa‐ and tetrahedrally coordinated Zn^II atoms, respectively. The di­amine ligands behave as N,N′‐bidentate ligands, while saccharinate (sac) is coordinated through the N atom. In (I), the complex lies about an inversion centre with the Zn atom disordered and displaced by 0.256 (2) Å from a centre of symmetry towards a sac N atom. The crystal structure of (I) is stabilized by N—H⋯O hydrogen bonds and the crystal packing of (II) is determined by hydrogen bonding as well as weak π–π stacking interactions between the sac ligands.     

(4,6‐Dimercapto‐1,3,5‐triazine‐2‐thiol­ato‐S2)­tris­(tri­phenyl­phosphine‐P)gold(I) di­methyl­form­amide solvate

In the title compound, [Au(C₃H₂N₃S₃)(C₁₈H₁₅P)₃]·C₃H₇NO, the Au^I atom has a distorted tetrahedral geometry consisting of one uncoordinated di­methyl­form­amide mol­ecule, one tri­thio­cyanurate ligand and three PPh₃ ligands. The S—Au distance is 2.909 (2) Å, and the P—Au distances fall in the range 2.400 (14)–2.4074 (13) Å. The S—Au—P angles are 92.81 (6), 99.17 (6) and 104.21 (5)°, and the P—Au—P angles are 114.46 (5), 119.04 (5) and 119.66 (5)°.