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In the title salt of an S-substituted dithiocarbazate, C16H16N3S2+·Cl−, the dihedral angles between the almost planar (r.m.s deviation = 0.005 Å) central CN2S2 residue and the terminal pyridinium and phenyl rings are 80.09 (11) and 3.82 (11)°, respectively, indicating the cation has an L-shape; the amine H and thione S atoms are syn. The conformation about each of the imine [1.376 (3) Å] and ethene [1.333 (4) Å] bonds is E. The shortened C—C bond [1.444 (4) Å] linking the double bonds is consistent with conjugation in this part of the molecule. In the crystal, supramolecular layers with a jagged topology are formed by charged-assisted amine-H...Cl− and pyridinium-N+—H...Cl− hydrogen bonds. The layers stack along the a axis with no specific directional interactions between them.

In the title salt, C14H17N2+·Cl−, the central N atom is pyramidal (sum of bond angles = 330.9°) and there is a near orthogonal relationship between the benzene rings [dihedral angle = 89.95 (10)°]. The crystal packing features N—H...Cl hydrogen bonds, which lead to a supramolecular undulating ribbon along the a axis comprising edge-shared eight-membered {...HNH...Cl}2 synthons. The chains are connected into layers in the ab plane by C—H...π interactions.

In the title compound, C16H15N3S2, the central C2N2S2 residue is planar (r.m.s. deviation = 0.045 Å) and the pyridyl and benzene rings are inclined and approximately coplanar to this plane, respectively [dihedral angles = 72.85 (9) and 10.73 (9)°], so that, overall, the molecule adopts an L-shape. The conformation about each of the N=C [1.290 (3) Å] and C=C [1.340 (3) Å] bonds is E. Supramolecular chains along [1-10] are stabilized by N—H...N(pyridine) hydrogen bonding and these are connected into a double layer that stacks along the c-axis direction by C—H...π(pyridine) interactions.

In the title compound, C26H24N2O2, the benzimidazole ring system is almost planar [maximum displacement = 0.025 (1) Å] and makes dihedral angles of 80.48 (5) and 41.57 (5)° with the benzene rings, which are inclined to one another by 65.33 (6)°. In the crystal, molecules are linked via C—H...π and weak π–π interactions [centroid–centroid distance = 3.8070 (7) Å and interplanar distance = 3.6160 (5) Å].

The title compound, C17H16N2O3, has an E conformation about the azobenzene (–N=N–) linkage. The benzene rings are twisted slightly with respect to each other [6.79 (9)°], while the dihedral angle between the plane through the carboxy group and the attached benzene ring is 3.2 (2)°. In the crystal, molecules are oriented with the carboxy groups head-to-head, forming O—H...O hydrogen-bonded inversion dimers. These dimers are connected by C—H...O hydrogen-bonds into layers lying parallel to the (013) plane.

The asymmetric unit of the title compound, C14H20Br2O2, contains one half-molecule located on an inversion centre. The molecule is essentially planar, with a maximum deviation from the best plane of the non-H atoms of 0.054 (2) Å for the O atoms. The butoxy group adopts a fully extended all-trans conformation. In the crystal, molecules are connected via C—Br...O halogen bonds [Br...O = 3.2393 (19) Å] into a two-dimensional corrugated network in the bc plane.

The ZnII atom in the title compound, [Zn(C6H12NOS2)Cl(C10H8N2)], is coordinated by a chelating N-2-hydroxyethyl-N-isopropyldithiocarbamate ligand, a 2,2′-bipyridine ligand and a Cl atom. The resulting ClN2S2 donor set defines a distorted square-pyramidal coordination geometry. Helical supramolecular chains sustained by O—H...S hydrogen bonds and propagating along the b axis feature in the crystal packing. A three-dimensional architecture is stabilized by C—H...O, C—H...S and C—H...Cl interactions.

The asymmetric unit of the title compound, C26H34O2S2, comprises one half-molecule located on an inversion centre. The thiophene groups are twisted relative to the benzene ring, making a dihedral angle of 5.30 (7)°, and the n-hexyl groups are in a fully extended conformation. In the crystal, there are short C—H...π contacts involving the thiophene groups.

In the title hydrazonodithioate, C21H19N3OS2, the amide group is twisted out of the plane through the S2C=N atoms: the C—N—N—C torsion angle is 139.71 (13)°. The pyridine ring forms dihedral angles of 52.96 (8) and 86.46 (8)° with the phenyl rings, and the latter are approximately orthogonal [dihedral angle = 76.42 (9)°]. Supramolecular chains sustained by N—H...O hydrogen bonds and propagated by glide symmetry along the c axis are found in the crystal structure. The chains are consolidated into a three-dimensional architecture by C—H...O and C—H...N interactions.

In the title disulfide, C16H18S2, the molecule is twisted about the central S—S bond [the C—S—S—C torsion angle = 93.24 (7)°] and the dihedral angle between the benzene rings is 72.84 (7)°, indicating an almost orthogonal relationship; the methyl groups are orientated to the same side of the molecule. The crystal packing features C—H....π interactions which consolidate a three-dimensional architecture.

The complete molecule of the title complex, [Ni(C19H21N2OS2)2], is generated by the application of twofold symmetry. The NiII atom is N,S-chelated by two hydrazinecarbodithioate ligands, which provide an N2S2 donor set that defines a distorted square-planar geometry, the S atoms being approximately cis. The conformation of the chelate ring is an envelope with the NiII atom being the flap atom. The dihedral angle between the least-squares planes through the chelate rings = 30.10 (6)°. Supramolecular chains propagated by glide symmetry along the c axis and mediated by C—H...N contacts feature in the crystal packing.

In the title compound, C15H16N2S2, the central C2N2S2 unit is essentially planar (r.m.s. deviation = 0.047 Å) and forms dihedral angles of 68.26 (4) and 65.99 (4)° with the phenyl and benzene rings, respectively, indicating a twisted molecule. Supramolecular chains with a step topology and propagating along [100] feature in the crystal packing, mediated through N—H...S hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C—H...π interactions.

The asymmetric unit of the title compound, [Ni(C15H14N3S2)2], consists of two independent molecules with similar configurations. Each Ni2+ cation is coordinated in a cis-mode by two tridentate N,N′,S-chelating Schiff base ligands, creating a distorted octahedron [the smallest angle being 77.57 (7)° and the widest being 168.97 (7)° for one molecule, and 78.04 (7) and 167.55 (7)° for the second molecule]. The dihedral angle between the mean coordination planes of the two ligands is 86.76 (7)° for one and 89.99 (7)° for the second molecule. π–π interactions between neighbouring pyridine rings with plane-to-plane distances of 3.540 (1) and 3.704 (1) Å are observed.

The title compound, [Zn(C15H14N3S2)2], contains two chemically equivalent Schiff base anions that are coordinated to the ZnII ion as tridentate N,N′,S-chelating ligands, creating a distorted octahedral environment [the smallest angle being 75.40 (6)° and the widest angle being 162.87 (6)°], with the two S atoms in cis positions. The dihedral angle between the mean planes of the two coordinating ligands is 85.65 (5)°. Weak C—H...S hydrogen bonds are also observed.

Two independent molecules comprise the asymmetric unit of the title compound, C13H19N3OS, which differ in the conformations of the residues linking the thiourea and the terminal benzene ring, as manifested in the Cm—Cm—Ca—Ca torsion angles [78.03 (16) and −93.64 (16)°, respectively; m = methylene and a = aromatic]. The dihedral angles [84.40 (4) and 88.28 (5)°] formed between the thiourea residue and the benzene ring indicate an almost orthogonal relationship. In each thiourea residue, the N—H hydrogen atoms are anti, and the terminal N—H hydrogen atom forms an intramolecular N—H...N hydrogen bond with the imine-N atom. In each case, the conformation about the imine C=N double bond [1.2812 (17) and 1.2801 (17) Å] is E. In the crystal, the molecules are connected by N—H...S hydrogen bonds and these are connected into four molecule aggregates via N—H...O hydrogen bonds, which are assembled into a two-dimensional array parallel to (011) via C—H...π and π–π interactions [ring centroid–centroid distance = 3.8344 (9) Å].

In the title compound, [Zn(C20H16N3S2)2]·CH3CN, two different Schiff base moieties coordinate to the central ZnII ion as tridentate N,N′,S-chelating ligands, creating a distorted octahedral environment [the smallest angle being 73.24 (6)° and the widest angle being 155.73 (7)°], with the two S atoms in cis positions. The dihedral angle between the mean planes of the two coordinating ligands is 83.65 (5)°. The crystal packing is consolidated by weak C—H...N hydrogen-bonding interactions.

The title compound congestiflorone, C28H32O4, which was isolated from the stem bark of Mesua congestiflora, consists of a benzophenone skeleton with two attached pyran rings to which a cyclohexane ring and a C6 side chain are bonded. The benzene ring is significantly distorted from planarity (r.m.s. deviation = 0.0007 Å) due to the constraints imposed by junctions with the two pyran rings. The cyclohexane ring is in a chair conformation, one pyran ring is in a boat conformation, while the other is a distorted chair. The phenyl and benzene rings make a dihedral angle of 55.85 (9)°. An intramolecular O—H...O hydrogen bond is observed. In the crystal, molecules are linked via C—H...O interactions.

The structure of the title compound, [Ni(C15H14N3S2)2]·H2O, has one molecule in the asymmetric unit, along with a solvent water molecule. The two different Schiff base moieties coordinate to the central NiII ion as tridentate N,N′,S-chelating ligands, creating a six-coordinate distorted octahedral environment [the smallest angle being 77.43 (7)° and the widest angle being 169.99 (7)°]. The mean planes of the two ligands are nearly orthogonal to each other with an angle of 89.53 (6)°. The packing of the complex is supported by O—H...N and O—H...S hydrogen bonding between the solvent water molecule and the uncoordinated N and S atoms of neighbouring ligands.

In the title compound, C11H12N4S, the thiophene ring is roughly planar, with a maximum deviation of 0.012 (1) Å for the S atom, and makes a dihedral angle of 7.89 (8)° with the mean plane of the piperidine ring, which is in a chair conformation. The crystal packing is stabilized by pairs of centrosymmetric intermolecular N—H...N hydrogen bonds, which results in the formation of a step-wise chain parallel to [10overline1].

The title compound, [Sn(C4H9)2(C9H10NS2)2], features a tetrahedrally coordinated SnIV atom; the dithiocarbamate ligands coordinate in a monodentate fashion, accompanied by two n-butyl chains. The non-coordinating thione S atoms are each proximate to the SnIV atom [3.0136 (7) and 2.9865 (8) Å], giving rise to distortions from the ideal geometry as evident in the wide C—Sn—C bond angle of 139.06 (12) °. In the crystal, C—H...S interactions lead to the formation of a linear supramolecular chain along the b axis. The chains are aligned into layers by C—H...π interactions, and the layers stack along [001]. One of the ethyl groups is statistically disordered over two sets of sites.

In the title compound, C12H14N2OS, the pyrrolidine ring adopts an envelope conformation with the C atom at the 3-position as the flap and makes a dihedral angle of 65.80 (9)° with the benzene ring. In the crystal, N—H...O hydrogen bonds join c-glide related molecules into chains extended along [001] that are further connected into (100) layers via C—H...O interactions.

The title compound, [Sn(C6H5)3(C9H10NS2)], has two independent molecules in the asymmetric unit and each features a tetrahedrally coordinated SnIV atom as the dithiocarbamate ligand coordinates in a monodentate fashion. As the non-coordinating thione S atom is proximate to the Sn atom [Sn...S(thione) = 3.1477 (6) and 2.9970 (5) Å for the independent molecules], distortions from the ideal geometry are evident [the widest angle being 120.48 (5)°]. The most notable feature of the crystal packing is the formation of C—H...π interactions that lead to the formation of supramolecular layers parallel to (overline{3}2overline{1}).

The title dammarane triterpenoid, C30H50O4, assigned the name chrysura, was isolated from an ethyl acetate extract of Walsura chrysogyne leaves (Meliaceae). It has 20S*,24S* relative stereochemistry and an oxepanone ring with two methyl groups at position 4. The two cyclohexane rings adopt chair conformations. The cyclopentane and tetrahydrofuran rings have envelope conformations; their mean planes make a dihedral angle of 13.1 (3)°, indicating that the rings are only slightly tilted with respect to each other. There is an intramolecular C—H...O hydrogen bond in the molecule, which forms S(6) and S(7) ring motifs. In the crystal, molecules are linked via O—H...O and C—H...O hydrogen bonds, forming chains propagating along [001] which stack along the b-axis direction.

In the title compound, C13H18N2O2S, the 4-methoxybenzoyl fragment is approximately planar [maximum deviation = 0.057 (2) Å] and twisted relative to the thioamide fragment, forming a dihedral angle of 86.62 (6)°. The two Csp2—Nsp2 bonds in the thiourea unit differ significantly in length [1.327 (2) and 1.431 (2) Å]. In the crystal, N—H...O hydrogen bonds link the molecules into chains parallel to [010].

The title molecule, C22H22Br4O2S2, is centrosymmetric with an inversion centre located at the centre of the benzene ring. The 3,5-dibromothiophene groups are twisted relative to the benzene ring, making a dihedral angle of 41.43 (9)°.

In the title compound, C9H12N4O, the piperidine ring adopts a chair conformation and makes a dihedral angle of 42.49 (11)° with the approximately planar pyrazole moiety [maximum deviation = 0.038 (2) Å]. In the crystal, N—H...O and N—H...N hydrogen bonds and a weak C—H...O interaction link the molecules into sheets lying parallel to (110).

In the title compound, C19H29NO, the C—C and C—N bond distances of the benzonitrile group are 1.445 (2) and 1.157 (2) Å, respectively. The aliphatic fragment adopts a bent zigzag arangement which differs from the planar zigzag arrangement normally observed in n-alkanes or long-chain alkylbenzenes. In the crystal, inversion dimers linked by pairs of C—H...O hydrogen bonds occur. A C—H...N interaction also occurs. In the crystal, molecules are packed with the nitrile and aliphatic groups oriented in a head-to-tail fashion involving, forming a ripple-like motif along the a axis.

The title compound [systematic name: 5,10-dihydroxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)pyrano[3,2-b]xanthen-6(2H)-one], C23H22O5, isolated from the stem bark of Calophyllum soulattri, consists of four six-membered rings and a 2-methylbut-3-en-2-yl side chain. The tricyclic xanthone ring system is almost planar [maximum deviation = 0.093 (2) Å], whereas the pyranoid ring is in a distorted boat conformation. The 2-methylbut-3-en-2-yl side chain is in a synperiplanar conformation. There are two intramolecular O—H...O hydrogen bonds. In the crystal, molecules are linked by C—H...O interactions, forming a zigzag chain propagating in [010].

In the structure of the title compound, C20H24N2S2, the central CN2S2 atoms are planar (r.m.s. deviation = 0.0205 Å) but both benzene rings are twisted out of this plane forming dihedral angles of 23.03 (6) and 84.75 (4)° (tolyl); the n-butyl group occupies a position normal to the plane [N—C—C—C torsion angle = −84.33 (16)°]. The conformation of the imine bond [1.2888 (18) Å] is E. The syn arrangement of the thione S and amino H atoms enables the formation of N—H...S hydrogen bonds between centrosymmetrically related molecules. These lead to eight-membered {...HNC=S}2 synthons which are further stabilized by proximate C—H...S interactions. The resulting dimeric aggregates are connected into a supramolecular chain along the c axis by C—H...π(tolyl) interactions.

The ZnII atom in the title compound, [Zn(C5H10NS2)2(C12H8N2)], exists in a distorted cis-octahedral N2S4 donor set defined by two chelating dithiocarbamate anions as well as a 1,10-phenanthroline ligand. Each of the ligands coordinates in a symmetric mode. The crystal packing is stabilized by weak C—H...S, C—H...π(ZnS2C) and π–π [ring centroid distance between centrosymmetrically related pyridyl rings = 3.5955 (13) Å] interactions.

The title compound, [Sn(C6H5)3(C11H14NS2)], features a tetrahedrally coordinated Sn atom, as the dithiocarbamate ligand coordinates in a monodentate fashion. Due to the proximity of the non-coordinating thione S atom, distortions from ideal tetrahedral geometry about the metal atom are evident with the widest C—Sn—S angle being 117.26 (5)°. In the crystal, molecules are linked by C—H...S interactions, which generate helical supramolecular chains along the b axis.

The CdII atom in the title compound, [Cd(C5H10NS2)2(C10H8N2)], exists in an N2S4 donor set defined by two chelating dithiocarbamate anions as well as a 2,2′-bipyridine ligand. The coordination geometry approximates a trigonal prism. The crystal packing features weak C—H...S interactions, leading to linear supramolecular chains along the a axis. The primary connections between these are by π–π stacking interactions [ring centroid distance between centrosymmetrically related pyridyl rings = 3.7455 (10) Å]. Overall, the crystal structure may be described as comprising double layers of molecules that stack along the b axis.

The title compound, Artonol B, C24H20O7, isolated from the stem bark of Artocarpus kemando, consists of four six-membered rings and one five-membered ring. The tricyclic xanthone ring system is almost planar [maximum deviation 0.115 (5) Å], whereas the pyranoid ring is in a distorted boat conformation·The furan ring is almost coplanar with the fused aromatic ring, making a dihedral angle of 3.76 (9)°. The phenol ring serves as a intramolecular hydrogen-bond donor to the adjacent carbonyl group and also acts as an intermolecular hydrogen-bond acceptor for the methyl groups of adjacent molecules, forming a three-dimensional network in the crystal.

The title compound (trivial name α-mangostin), C24H26O6, isolated from Cratoxylum glaucum, is characterized by a xanthone skeleton of three fused six-membered rings and two 3-methylbut-2-enyl side chains. The three rings in the structure are nearly coplanar, with an r.m.s. deviation for the tricyclic ring system of 0.0014 Å. The two 3-methylbut-2-enyl side chains are in (+)-synclinal and (-)-anticlinal conformations. Intramolecular O—H...O and C—H...O interactions occur. The crystal structure is stabilized by intermolecular O—H...O, C—H...O and C—H...π interactions.

The SnIV atom in the title compound, [Sn(C6H5)(C14H19N4S)Cl2], exists within a distorted octahedral geometry defined by the N,N′,S-tridentate monodeprotonated Schiff base ligand, two mutually trans Cl atoms, and the ipso-C atom of the Sn-bound phenyl group; the latter is trans to the azo-N atom. The greatest distortion from the ideal geometry is found in the nominally trans angle formed by the S and pyridyl-N atoms at Sn [151.03 (4)°]. With the exception of the cyclohexyl group (chair form), the Schiff base ligand is almost planar (r.m.s. deviation of non-H and Sn atoms = 0.053 Å). The nearly orthogonal orientation of the Sn-bound phenyl group [N—Sn—C—C torsion angle = 70.8 (5)°] to the planar portion of the Schiff base allows for the formation of significant intramolecular C—H...Cl interactions which preclude the Cl atoms from participating in N—H...Cl hydrogen bonds. Instead, C—H...π contacts, involving methylene H and the Sn-bound phenyl group, lead to the formation of supramolecular chains that pack in the bc plane. Connections between these layers are of the type C—H...Cl.

The SnIV atom in the title organotin dithiocarbamate, [Sn(C6H5)2(C11H14NS2)Cl], is penta-coordinated by an asymmetrically coordinating dithiocarbamate ligand, a Cl and two ispo-C atoms of the Sn-bound phenyl groups. The resulting C2ClS2 donor set defines a coordination geometry intermediate between square-pyramidal and trigonal-bipyramidal with a slight tendency towards the latter. The formation of close intramolecular C–H...Cl and C–H...S contacts precludes the Cl and S atoms from forming significant intermolecular contacts. The presence of C–H...π contacts leads to the formation of supramolecular arrays that stack along the b axis.

Two independent but very similar molecules comprise the asymmetric unit of the title compound, [Zn(C8H16NS2)2(C12H8N2)]. The N2S4 donor set about Zn is defined by two symmetrically chelating dithiocarbamate ligands and a 1,10-phenanthroline ligand. Distortions from the ideal octahedral coordination geometry arise from the restricted bite angles of the ligands. The main feature of the crystal packing is the formation of tetrameric supramolecular aggregates mediated by C—H...S interactions. Disorder was found in each of the sec-butyl groups. This was resolved over two positions in each case with the major components of the disorder having site occupancies in the range 0.551 (6)–0.725 (5).

In the mononuclear complex molecule of the title compond, [ZnCl2(C18H18N2O)2]·2C18H18N2O, the Zn atom, which lies on a twofold rotation axis, is coordinated by phenolate O atoms in a tetrahedral coordination geometry. The coordinated Schiff base uses its indole NH donor site to form a hydrogen bond to the negatively charged phenolate O atom of the uncoordinated zwitterionic Schiff base. There is an intramolecular N—H...O hydrogen bond in the coordinated and uncoordinated Schiff bases. The indole NH site of the uncoordinated Schiff base does not engage in a hydrogen-bond interaction. The CH2—CH2 group in the uncoordinated Schiff base is disordered equally over two positions.