Erratum: N'-[Bis(benzyl-sulfan-yl)methyl-idene]benzo-hydrazide. Corrigendum.

[This corrects the article DOI: 10.1107/S1600536812019472.].

Crystal structure of 4-methyl-benzyl N'-[(thio-phen-2-yl)methyl-idene]hydrazinecarbodi-thio-ate.

In the title compound, C15H16N2S3 {systematic name: [({[(4-methyl-phen-yl)meth-yl]sulfan-yl}methane-thio-yl)amino][1-(thio-phen-2-yl)ethyl-idene]amine}, the central CN2S2 residue is almost planar (r.m.s. deviation = 0.0061 Å) and forms dihedral angles of 7.39 (10) and 64.91 (5)° with the thienyl and p-tolyl rings, respectively; the dihedral angle between these rings is 57.52 (6)°. The non-thione S atoms are syn, and with respect to the thione S atom, the benzyl group is anti. In the crystal, centrosymmetrically related mol-ecules self-associate via eight-membered {⋯HNCS}2 synthons. The dimeric aggregates stack along the a axis and are are consolidated into a three-dimensional architecture via methyl-C-H⋯π(benzene) and benzene-C-H⋯π(thien-yl) inter-actions.

Crystal structure of benzyl 3-(3-methyl-phen-yl)di-thio-carbazate.

In the title compound, C15H16N2S2, the central CN2S2 residue is almost planar (r.m.s. deviation = 0.0354 Å) and forms dihedral angles of 56.02 (4) and 75.52 (4)° with the phenyl and tolyl rings, respectively; the dihedral angle between the aromatic rings is 81.72 (5)°. The conformation about the N-N bond is gauche [C-N-N-C = -117.48 (15)°]. Overall, the mol-ecule has the shape of the letter L. In the crystal packing, supra-molecular chains along the a axis are formed by N-H⋯S(thione) hydrogen bonds whereby the thione S atom accepts two such bonds. The hydrogen bonding leads to alternating edge-shared eight-membered {⋯HNCS}2 and 10-membered {⋯HNNH⋯S}2 synthons. The chains are connected into layers by phen-yl-tolyl C-H⋯π inter-actions; the layers stack along the c axis with no specific inter-actions between them.

Crystal structure of 2-((1E)-{2-[bis-(2-methyl-benzyl-sulfan-yl)methyl-idene]hydrazin-1-yl-idene}meth-yl)-6-meth-oxy-phenol.

In the title compound, C25H26N2O2S2, the central CN2S2 atoms are almost coplanar (r.m.s. deviation = 0.0058 Å). One phenyl ring clearly lies to one side of the central plane, while the other is oriented in the plane but splayed. Despite the different relative orientations, the phenyl rings form similar dihedral angles of 64.90 (3) and 70.06 (3)° with the central plane, and 63.28 (4)° with each other. The benzene ring is twisted with respect to the central plane, forming a dihedral angle of 13.17 (7)°. The S2C=N, N-N and N-N=C bond lengths of 1.2919 (19), 1.4037 (17) and 1.2892 (19) Å, respectively, suggest limited conjugation over these atoms; the configuration about the N-N=C bond is E. An intra-molecular O-H⋯N hydrogen bond is noted. In the crystal, phen-yl-meth-oxy C-H⋯O and phen-yl-phenyl C-H⋯π inter-actions lead to supra-molecular double chains parallel to the b axis. These are connected into a layer via meth-yl-phenyl C-H⋯π inter-actions, and layers stack along the a axis, being connected by weak π-π inter-actions between phenyl rings [inter-centroid distance = 3.9915 (9) Å] so that a three-dimensional architecture ensues.

Crystal structure of 2'-hy-droxy-aceto-phenone 4-methyl-thio-semicarbazide.

In the organic mol-ecule of the title hydrate, C11H15N3OS·H2O, {systematic name: 3-ethyl-1-{(E)-[1-(2-hy-droxy-phen-yl)ethyl-idene]amino}-thio-urea monohydrate}, a dihedral angle of 5.39 (2)° is formed between the hy-droxy-benzene ring and the non-H atoms comprising the side chain (r.m.s. deviation = 0.0625 Å), with the major deviation from planarity noted for the terminal ethyl group [the C-N-C-C torsion angle = -172.17 (13)°]. The N-H H atoms are syn and an intra-molecular hy-droxy-imine O-H⋯N hydrogen bond is noted. In the crystal, the N-bonded H atoms form hydrogen bonds to symmetry-related water mol-ecules, and the latter form donor inter-actions with the hy-droxy O atom and with a hy-droxy-benzene ring, forming a O-H⋯π inter-action. The hydrogen bonding leads to supra-molecular tubes aligned along the b axis. The tubes are connected into layers via C-H⋯O inter-actions, and these stack along the c axis with no directional inter-actions between them.

Crystal structure of 3-methyl-pyridine-2-carbaldehyde 4-methyl-thio-semi-carba-zone monohydrate.

In the title hydrate, C9H12N4S·H2O (systematic name: 3-methyl-1-{(E)-[(3-methyl-pyridin-2-yl)methyl-idene]amino}-thio-urea monohydrate), a small twist is noted between the pyridine ring and the rest of the organic mol-ecule [dihedral angle = 6.96 (5)°]. The imine and pyridine N atoms are syn, and the amine H atoms are anti. The latter arrangement allows for the formation of an intra-molecular N-H⋯N(imine) hydrogen bond. Both the N-bonded H atoms form hydrogen bonds to symmetry-related water mol-ecules, and the latter forms O-H hydrogen bonds with the pyridine N and thione S atoms. These inter-actions lead to supra-molecular layers that stack along the a-axis direction with no specific inter-actions between them.

Crystal structure of 1-{(Z)-[(2E)-3-(4-chloro-phen-yl)-1-phenyl-prop-2-en-1-yl-idene]amino}-3-ethyl-thio-urea.

In the title thio-semicarbazone compound, C18H18ClN3S, the CN3S residue is almost planar (r.m.s. deviation = 0.0031 Å) and forms dihedral angles of 65.99 (7) and 34.60 (10)° with the phenyl and chloro-benzene rings, respectively; the dihedral angle between the aromatic rings is 85.13 (8)°. The conformation about the C=N bond is Z, and that about the C=C bonds is E. The imine N and ethyl N atoms are syn and are linked by an eth-yl-imine N-H⋯N hydrogen bond. This H atom also forms an inter-molecular hydrogen bond to the thione S atom, resulting in a supra-molecular helical chain propagating along the b axis. The chains are consolidated into a three-dimensional architecture by phenyl-C-H⋯Cl contacts and weak π-π inter-actions between centrosymmetrically related chloro-benzene rings [inter-centroid distance = 3.9127 (15) Å].

Crystal structure of (Z)-4-methylbenzyl 3-[1-(5-methylpyridin-2-yl)ethylidene]dithiocarbazate.

In the title di-thio-carbazate compound, C17H19N3S2, the central CN2S2 residue is essentially planar (r.m.s. deviation = 0.0288 Å) and forms dihedral angles of 9.77 (8) and 77.47 (7)° with the substituted-pyridyl and p-tolyl rings, respectively, indicating a highly twisted mol-ecule; the dihedral angle between the rings is 85.56 (8)°. The configuration about the C=N bond is Z, which allows for the formation of an intra-molecular N-H⋯N(pyrid-yl) hydrogen bond. The packing features tolyl-methyl-C-H⋯N(imine), pyridyl-C-H⋯π(tol-yl) and π-π inter-actions [between pyridyl rings with a distance = 3.7946 (13) Å], which generates jagged supra-molecular layers that stack along the b axis with no directional inter-actions between them.

Crystal structure of 2-{[2-(3-phenyl-allyl-idene)hydrazin-1-yl]thio-carbonyl-sulfanylmeth-yl}pyridinium chloride.

In the title salt of an S-substituted di-thio-carbazate, 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 mol-ecule. In the crystal, supra-molecular 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 inter-actions between them.

2,2-Dibenzyl-hydrazin-1-ium chloride.

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 supra-molecular 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 inter-actions.

(Pyridin-4-yl)methyl N'-(3-phenyl-allyl-idene)hydrazinecarbodithio-ate.

In the title compound, C(16)H(15)N(3)S(2), the central C(2)N(2)S(2) 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 mol-ecule 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. Supra-molecular 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) inter-actions.

Bis{benzyl 2-[4-(4-meth-oxy-phen-yl)butan-2-yl-idene]hydrazinecarbodithio-ato-κ(2)N(2),S}nickel(II).

The complete mol-ecule of the title complex, [Ni(C(19)H(21)N(2)OS(2))(2)], is generated by the application of twofold symmetry. The Ni(II) atom is N,S-chelated by two hydrazinecarbodithio-ate ligands, which provide an N(2)S(2) 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 Ni(II) atom being the flap atom. The dihedral angle between the least-squares planes through the chelate rings = 30.10 (6)°. Supra-molecular chains propagated by glide symmetry along the c axis and mediated by C-H⋯N contacts feature in the crystal packing.

N'-[Bis(benzyl-sulfan-yl)methyl-idene]benzohydrazide.

In the title hydrazonodithio-ate, C(21)H(19)N(3)OS(2), the amide group is twisted out of the plane through the S(2)C=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)°]. Supra-molecular 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 inter-actions.

1-Methyl-2-({[(2-methyl-phen-yl)meth-yl]disulfan-yl}meth-yl)benzene.

In the title disulfide, C(16)H(18)S(2), the mol-ecule 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 mol-ecule. The crystal packing features C-H⋯.π inter-actions which consolidate a three-dimensional architecture.

Bis{S-benzyl 3-[(6-methyl-pyridin-2-yl)methyl-idene]dithio-carbazato}nickel(II).

The asymmetric unit of the title compound, [Ni(C(15)H(14)N(3)S(2))(2)], consists of two independent mol-ecules with similar configurations. Each Ni(2+) cation is coordinated in a cis-mode by two tridentate N,N',S-chelating Schiff base ligands, creating a distorted octa-hedron [the smallest angle being 77.57 (7)° and the widest being 168.97 (7)° for one mol-ecule, and 78.04 (7) and 167.55 (7)° for the second mol-ecule]. 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 mol-ecule. π-π inter-actions between neighbouring pyridine rings with plane-to-plane distances of 3.540 (1) and 3.704 (1) Šare observed.

Benzyl 3-(2-methyl-phen-yl)dithio-carbazate.

In the title compound, C(15)H(16)N(2)S(2), the central C(2)N(2)S(2) 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 mol-ecule. Supra-molecular 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 inter-actions.

1-{(E)-[4-(4-Meth-oxy-phen-yl)butan-2-yl-idene]amino}-3-methyl-thio-urea.

Two independent mol-ecules comprise the asymmetric unit of the title compound, C(13)H(19)N(3)OS, which differ in the conformations of the residues linking the thio-urea and the terminal benzene ring, as manifested in the C(m)-C(m)-C(a)-C(a) torsion angles [78.03 (16) and -93.64 (16)°, respectively; m = methyl-ene and a = aromatic]. The dihedral angles [84.40 (4) and 88.28 (5)°] formed between the thio-urea residue and the benzene ring indicate an almost orthogonal relationship. In each thio-urea residue, the N-H hydrogen atoms are anti, and the terminal N-H hydrogen atom forms an intra-molecular 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 mol-ecules are connected by N-H⋯S hydrogen bonds and these are connected into four mol-ecule 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 inter-actions [ring centroid-centroid distance = 3.8344 (9) Å].

2-Cyclo-hexyl-idene-N-methyl-hydrazine-carbothio-amide.

The title compound C(8)H(15)N(3)S has two mol-ecules in the asymmetric unit in which cis-trans isomerism is exhibited around the N(NH)C=S bonds. The cyclo-hexyl rings in both mol-ecules adopt a chair conformation. In the crystal, N-H⋯S hydrogen bonding produces dimers, which are inter-connected through further N-H⋯S hydrogen bonds, forming chains along the b-axis direction.