In the title β-thio-carbonyl compound, C16H16O3S, the adjacent meth-oxy and carbonyl O atoms are synperiplanar [the O-C-C-O torsion angle is 19.8 (4)°] and are separated by 2.582 (3) Å. The dihedral angle between the rings is 40.11 (16)°, and the meth-oxy group is coplanar with the benzene ring to which it is connected [the C-C-O-C torsion angle is 179.1 (3)°]. The most notable feature of the crystal packing is the formation of methine and methyl C-H⋯O(carbon-yl) inter-actions that lead to a supra-molecular chain with a zigzag topology along the c axis. Chains pack with no specific inter-molecular inter-actions between them.
In the title salt, C5H7N(+)·C6H3ClNO(-), the 2-amino-pyri-din-ium cation inter-acts with the carboxyl-ate group of the 6-chloro-nicotinate anion through a pair of independent N-H⋯O hydrogen bonds, forming an R 2 (2)(8) ring motif. In the crystal, these dimeric units are connected further via N-H⋯O hydrogen bonds, forming chains along [001]. In addition, weak C-H⋯N and C-H⋯O hydrogen bonds, together with weak π-π inter-actions, with centroid-centroid distances of 3.6560 (5) and 3.6295 (5) Å, connect the chains, forming a two-dimensional network parallel to (100).
In the title compound, C16H17N3OS, a benzoyl thio-urea derivative, the planes of the pyridine and benzene rings are inclined to one another by 66.54 (9)°. There is an intra-molecular N-H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal, mol-ecules are linked via pairs of N-H⋯N hydrogen bonds, forming inversion dimers, which are reinforced by pairs of C-H⋯S hydrogen bonds. The dimers are linked via C-H⋯π inter-actions, forming ribbons along [010].
In the crystal of the title mol-ecular salt, C7H9N6O(+)·NO3 (-), the cations and anions are linked via N-H⋯O and O-H⋯O hydrogen bonds, forming sheets parallel to (100). Within the sheets there are numerous hydrogen-bonding ring motifs.
There are two mol-ecules in the asymmetric unit of the title compound, C9H10N2OS. In one, the dihedral angle between the aromatic ring and the carbamo-thioyl group is 52.31 (7)° and in the other it is 36.16 (6)°. Each mol-ecule features an intra-molecular N-H⋯O hydrogen bond, which generates an S(6) ring and the O and S atoms have an anti disposition. In the crystal, mol-ecules are linked by N-H⋯S and N-H⋯O hydrogen bonds, generating separate [130] and [1-30] infinite chains. Weak C-H⋯O and C-H⋯S inter-actions are also observed.
In the title compound, C10H11NO2S2, the 1,3-di-thiane ring has a chair conformation with the 1,4-disposed C atoms being above and below the remaining four atoms. The nitro-benzene substituent occupies an equatorial position and forms a dihedral angle of 88.28 (5)° with the least-squares plane through the 1,3-di-thiane ring. The nitro group is twisted out of the plane of the benzene ring to which it is connected, forming a dihedral angle of 10.12 (3)°. In the crystal, mol-ecules aggregate into supra-molecular zigzag chains (glide symmetry along the c axis) via nitro-benzene N-O⋯π [N-O⋯Cg(benzene) = 3.4279 (18) Å and angle at O = 93.95 (11)°] inter-actions. The chains pack with no specific inter-molecular inter-actions between them.
In the title compound, C21H17N3OSe, the dihedral angles between the central five-membered ring and the C- and N-bound rings are 17.89 (10) and 42.35 (10)°, respectively, indicating the mol-ecule is twisted. The dihedral angle between the Se-bound rings is 85.36 (10)°. A close intra-molecular Se⋯O contact of 2.8507 (13) Å is noted. In the crystal, C-H⋯O, C-H⋯N and C-H⋯π inter-actions lead to the formation of supra-molecular layers parallel to (011); these stack with no specific inter-molecular inter-actions between them.
In the title compound, C23H21N3Se, the C-bound phenyl ring is almost coplanar with the central five-membered ring [dihedral angle = 2.84 (10)°], but the N-bound benzene ring is inclined [dihedral angle = 47.52 (10)°]. The dihedral angle between the Se-bound rings is 69.24 (9)°. An intra-molecular Se⋯N inter-action of 3.0248 (15) Å is noted. In the crystal, C-H⋯π inter-actions connect mol-ecules into double layers that stack along the a axis with no directional inter-actions between them.
In the title compound, C15H8O2S, the coumarin moiety is approximately planar (r.m.s. deviation of the 11 non-H atoms = 0.025 Å) and is slightly inclined with respect to the plane of the thio-phen-3-yl ring, forming a dihedral angle of 11.75 (8)°. In the crystal, the three-dimensional architecture features a combination of coumarin-thio-phene C-H⋯π and π-π [inter-centroid distance = 3.6612 (12) Å] inter-actions.
In the title compound, C15H15N3OS, there is an intra-molecular N-H⋯O hydrogen bond and an intra-molecular C-H⋯S hydrogen bond involving the C=O and C=S bonds which lie on opposite sides of the mol-ecule. The mol-ecule is non-planar with the benzene and pyridine rings being inclined to one another by 26.86 (9)°. In the crystal, mol-ecules are linked by pairs of N-H⋯S hydrogen bonds, forming inversion dimers with an R 2 (2)(8) ring motif. The dimers are linked via C-H⋯S hydrogen bonds, forming slabs parallel to the bc plane.
In the title compound, C15H15N3OS, the dihedral angle between the planes of the benzene and pyridine rings is 26.86 (9)°. Intra-molecular N-H⋯O and C-H⋯S hydrogen bonds both generate S(6) rings. The C=O and C=S bonds lie to opposite sides of the mol-ecule. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate R 2 (2)(8) loops.
The title indolin-2-one compound, C28H23FN4O·C2H6O, crystallizes as a 1:1 ethanol solvate. The ethanol mol-ecule is disordered over two positions with refined site occupancies of 0.560 (14) and 0.440 (14). The pyrazole ring makes dihedral angles of 84.16 (10) and 85.33 (9)° with the indolin-2-one and indole rings, respectively, whereas the dihedral angle between indolin-2-one and indole rings is 57.30 (7)°. In the crystal, the components are linked by N-H⋯O and O-H⋯O hydrogen bonds, forming an inversion mol-ecule-solvate 2:2 dimer with R 4 (4)(12) ring motifs. The crystal structure is consolidated by π-π inter-action between pairs of inversion-related indolin-2-one rings [inter-planar spacing = 3.599 (2) Å].
The title 2:1 co-crystal, 2C7H5NO4·C14H14N4O2, in which the complete di-amide mol-ecule is generated by crystallographic inversion symmetry, features a three-mol-ecule aggregate sustained by hydroxyl-O-H⋯N(pyrid-yl) hydrogen bonds. The p-nitro-benzoic acid mol-ecule is non-planar, exhibiting twists of both the carb-oxy-lic acid and nitro groups, which form dihedral angles of 10.16 (9) and 4.24 (4)°, respectively, with the benzene ring. The di-amide mol-ecule has a conformation approximating to a Z shape, with the pyridyl rings lying to either side of the central, almost planar di-amide residue (r.m.s. deviation of the eight atoms being 0.025 Å), and forming dihedral angles of 77.22 (6)° with it. In the crystal, three-mol-ecule aggregates are linked into a linear supra-molecular ladder sustained by amide-N-H⋯O(nitro) hydrogen bonds and orientated along [10-4]. The ladders are connected into a double layer via pyridyl- and benzene-C-H⋯O(amide) inter-actions, which, in turn, are connected into a three-dimensional architecture via π-π stacking inter-actions between pyridyl and benzene rings [inter-centroid distance = 3.6947 (8) Å]. An evaluation of the Hirshfeld surfaces confirm the importance of inter-molecular inter-actions involving oxygen atoms as well as the π-π inter-actions.
The asymmetric unit of the titled compound, C22H20FN5S, comprises two independent mol-ecules (A and B), both of which have a trans conformation with respect to the methene C=C [1.342 (2) and 1.335 (2) Å] and the acyclic N=C [1.283 (2) and 1.281 (2) Å] bonds. In mol-ecule A, the triazole ring makes dihedral angles of 55.01 (12) and 18.17 (9)° with the benzene and indole rings, respectively. The corresponding dihedral angles for mol-ecule B are 54.54 (11) and 14.60 (10)°, respectively. In the crystal, mol-ecules are consolidated into -A-B-A-B- chains along [010] via N-H⋯N hydrogen bonds. The chains are further linked into layers parallel to the ac plane via π-π inter-actions involving inversion-related triazole rings [centroid-centroid distances = 3.3436 (11)-3.4792 (13) Å].
The asymmetric unit of the title salt, C14H16N4O2 (2+)·2C9H5O6 (-), comprises half a dication, being located about a centre of inversion, and one anion, in a general position. The central C4N2O2 group of atoms in the dication are almost planar (r.m.s. deviation = 0.009 Å), and the carbonyl groups lie in an anti disposition to enable the formation of intra-molecular amide-N-H⋯O(carbon-yl) hydrogen bonds. To a first approximation, the pyridinium and amide N atoms lie to the same side of the mol-ecule [Npy-C-C-Namide torsion angle = 34.8 (2)°], and the anti pyridinium rings are approximately perpendicular to the central part of the mol-ecule [dihedral angle = 68.21 (8)°]. In the anion, one carboxyl-ate group is almost coplanar with the ring to which it is connected [Cben-Cben-Cq-O torsion angle = 2.0 (3)°], whereas the other carboxyl-ate and carb-oxy-lic acid groups are twisted out of the plane [torsion angles = 16.4 (3) and 15.3 (3)°, respectively]. In the crystal, anions assemble into layers parallel to (10-4) via hy-droxy-O-H⋯O(carbon-yl) and charge-assisted hy-droxy-O-H⋯O(carboxyl-ate) hydrogen bonds. The dications are linked into supra-molecular tapes by amide-N-H⋯O(amide) hydrogen bonds, and thread through the voids in the anionic layers, being connected by charge-assisted pyridinium-N-O(carboxyl-ate) hydrogen bonds, so that a three-dimensional architecture ensues. An analysis of the Hirshfeld surface points to the importance of O-H⋯O hydrogen bonding in the crystal structure.
In the title thio-semicarbazone, C11H15N3S, the p-tolyl-N-H and imino-N-H groups are anti and syn, respectively, to the central thione-S atom. This allows for the formation of an intra-molecular p-tolyl-N-H⋯N(imino) hydrogen bond. The mol-ecule is twisted with the dihedral angle between the p-tolyl ring and the non-hydrogen atoms of the N=CMe2 residue being 29.27 (8)°. The crystal packing features supra-molecular layers lying in the bc plane whereby centrosymmetric aggregates sustained by eight-membered thio-amide {⋯HNCS}2 synthons are linked by further N-H⋯S hydrogen bonds. Layers are connected via methyl-C-H⋯π inter-actions. The supra-molecular aggregation was further investigated by an analysis of the Hirshfeld surface and comparison made to related structures.
The title diorganotin compound, [Sn(CH3)2(C28H32N2O4)], features a distorted SnC2NO2 coordination geometry almost inter-mediate between ideal trigonal-bipyramidal and square-pyramidal. The dianionic Schiff base ligand coordinates in a tridentate fashion via two alkoxide O and hydrazinyl N atoms; an intra-molecular hy-droxy-O-H⋯N(hydrazin-yl) hydrogen bond is noted. The alk-oxy chain has an all-trans conformation, and to the first approximation, the mol-ecule has local mirror symmetry relating the two Sn-bound methyl groups. Supra-molecular layers sustained by imine-C-H⋯O(hy-droxy), π-π [between dec-yloxy-substituted benzene rings with an inter-centroid separation of 3.7724 (13) Å], C-H⋯π(arene) and C-H⋯π(chelate ring) inter-actions are formed in the crystal; layers stack along the c axis with no directional inter-actions between them. The presence of C-H⋯π(chelate ring) inter-actions in the crystal is clearly evident from an analysis of the calculated Hirshfeld surface.
The complete mol-ecule of the title hydrazine carbodi-thio-ate complex, [Ni(C19H21N2S2)2], is generated by the application of a centre of inversion. The NiII atom is N,S-chelated by two hydrazinecarbodi-thio-ate ligands, which provide a trans-N2S2 donor set that defines a distorted square-planar geometry. The conformation of the five-membered chelate ring is an envelope with the NiII atom being the flap atom. In the crystal, p-tolyl-C-H⋯π(benzene- i Pr), i Pr-C-H⋯π(p-tol-yl) and π-π inter-actions [between p-tolyl rings with inter-centroid distance = 3.8051 (12) Å] help to consolidate the three-dimensional architecture. The analysis of the Hirshfeld surface confirms the importance of H-atom contacts in establishing the packing.
The di-substituted acetyl-ene residue in the title compound, C11H11NO3, is capped at either end by di-methyl-hydroxy and 4-nitro-benzene groups; the nitro substituent is close to co-planar with the ring to which it is attached [dihedral angle = 9.4 (3)°]. The most prominent feature of the mol-ecular packing is the formation, via hy-droxy-O-H⋯O(hy-droxy) hydrogen bonds, of hexa-meric clusters about a site of symmetry . The aggregates are sustained by 12-membered {⋯OH}6 synthons and have the shape of a flattened chair. The clusters are connected into a three-dimensional architecture by benzene-C-H⋯O(nitro) inter-actions, involving both nitro-O atoms. The aforementioned inter-actions are readily identified in the calculated Hirshfeld surface. Computational chemistry indicates there is a significant energy, primarily electrostatic in nature, associated with the hy-droxy-O-H⋯O(hy-droxy) hydrogen bonds. Dispersion forces are more important in the other identified but, weaker inter-molecular contacts.
The asymmetric unit of the centrosymmetric title salt solvate, 2C17H17F6N2O+· C4H4O4 2-·CH3CH2OH, (systematic name: 2-{[2,8-bis-(tri-fluoro-meth-yl)quinolin-4-yl](hy-droxy)meth-yl}piperidin-1-ium butane-dioate ethanol monosolvate) comprises two independent cations, with almost superimposable conformations and each approximating the shape of the letter L, a butane-dioate dianion with an all-trans conformation and an ethanol solvent mol-ecule. In the crystal, supra-molecular chains along the a-axis direction are sustained by charge-assisted hy-droxy-O-H⋯O(carboxyl-ate) and ammonium-N-H⋯O(carboxyl-ate) hydrogen bonds. These are connected into a layer via C-F⋯π(pyrid-yl) contacts and π-π stacking inter-actions between quinolinyl-C6 and -NC5 rings of the independent cations of the asymmetric unit [inter-centroid separations = 3.6784 (17) and 3.6866 (17) Å]. Layers stack along the c-axis direction with no directional inter-actions between them. The analysis of the calculated Hirshfeld surface reveals the significance of the fluorine atoms in surface contacts. Thus, by far the greatest contribution to the surface contacts, i.e. 41.2%, are of the type F⋯H/H⋯F and many of these occur in the inter-layer region. However, these contacts occur at separations beyond the sum of the van der Waals radii for these atoms. It is noted that H⋯H contacts contribute 29.8% to the overall surface, with smaller contributions from O⋯H/H⋯O (14.0%) and F⋯F (5.7%) contacts.