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Review: 209 refs. [ABSTRACT FROM AUTHOR]

Advantages are the use of a heterogeneous, reusable catalyst and ligand-free conditions. [ABSTRACT FROM AUTHOR]

In the title compound, C14H11N3OS, the ace-naphthyl-ene ring system and hydrazinecarbo-thio-amide unit (=N-NH-C=S-NH-) are essentially coplanar [with maximum deviations from their mean planes of -0.009 (2) and 0.033 (2) Å, respectively], and make a dihedral angle of 1.59 (9)°. The mol-ecular conformation is stabilized by two weak intra-molecular hydrogen bonds (N-H⋯O and N-H⋯N), which generate S(6) and S(5) ring motifs. In the crystal, mol-ecules are linked by N-H⋯S hydrogen bonds, forming chains along [010]. The chains are linked via pairs of C-H⋯O hydrogen bonds, enclosing R (2) 2(10) ring motifs, and C-H⋯π inter-actions, forming a three-dimensional framework. The absolute structure of the title compound was determined by resonant scattering.

In the title compound, C12H11N3O2S, the dihedral angle between the 4H-chromen-4-one ring system and the -CH=N-NH-CS-NH- unit is 6.22 (1)°. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(14) loops. The dimers are reinforced by a pair of C-H⋯O inter-actions, which generate R 2 (2)(10) loops.

In the title compound, C17H20ClN3OS, the mean plane of the central thio-urea core makes dihedral angles of 26.56 (9) and 47.62 (12)° with the mean planes of the chromene moiety and the cyclo-hexyl ring, respectively. The cyclo-hexyl ring adopts a chair conformation. The N-H atoms of the thio-urea unit adopt an anti conformation. The chromene group is positioned trans, whereas the cyclo-hexyl ring lies in the cis position to the thione S atom, with respect to the thio-urea C-N bond. In the crystal, mol-ecules are linked by N-H⋯S hydrogen bonds, forming inversion dimers enclosing R (2) 2(8) ring motifs. The dimers are linked by C-H⋯Cl hydrogen bonds, enclosing R (6) 6(44) ring motifs, forming sheets lying parallel to (010).

The title compound, C26H42N4O2S2, adopts a shallow U-shape as both pendant arms of the 1,3-substituted benzene ring are orientated in the same direction. The thione S atoms lie to the same side of the benzene ring and the carbonyl O atoms to the other. The most prominent feature of the crystal packing is the formation of inversion dimers mediated by N-H⋯S hydrogen bonds. One of the 2-methyl-propyl groups is statistically disordered over two positions.

Two independent mol-ecules with quite similar conformations, A and B, comprise the asymmetric unit of the title compound, C23H21N3O2S. The terminal amide substituent is coplanar with the attached benzene ring [the O-C-C-C torsion angles are 174.0 (2) (A) and 6.3 (3)° (B)]. In the same way, the central amide group [C-C-C-O = 7.8 (3) (A) and 11.5 (3)° (B)] is approximately coplanar with the ring to which it is attached. A major twist is noted between the amide and adjacent thio-amide residues [C-N-C-S = -109.29 (19) (A) and -112.29 (19)° (B)]. In the crystal, supra-molecular chains along [100] are formed by N-H⋯O and N-H⋯S hydrogen bonding. These are connected into a three-dimensional architecture by C-H⋯π and π-π inter-actions [inter-centroid distance = 3.9157 (12) Å].

In the title compound, C17H25N3O2S, the terminal and central amide groups are, respectively, twisted and coplanar with the attached benzene ring [O-C-C-C torsion angles = 22.7 (3) and 5.4 (3)°]. In the central part of the mol-ecule, the amide and thio-amide residues are approximately perpendicular [C-N-C-S torsion angle = -104.98 (18)°]. Supra-molecular layers with a zigzag topology are formed in the crystal packing by N-H⋯O, N-H⋯S and C-H⋯O inter-actions; these stack along c, being separated by hydro-phobic inter-actions.

In the title compound, C15H14N2O2S, the central C2N2OS moiety is planar (r.m.s. deviation of fitted atoms = 0.0336 Å). This is ascribed to the formation of an S(6) loop stabilized by an intra-molecular N-H⋯O hydrogen bond; additional intramolecular N-H⋯O and C-H⋯S contacts are also noted. The dihedral angles between the central unit and the phenyl and benzene rings are 23.79 (7) and 29.52 (5)°, respectively. The thione S and ketone O atoms are mutually anti, as are the N-H H atoms; the O atoms lie to the same side of the mol-ecule. Centrosymmetric eight-membered {⋯HNC=S}2 synthons feature in the crystal packing. The resulting inversion dimers stack along the a axis and are connected into a three-dimensional structure by C-H⋯O and C-H⋯π inter-actions.

In the title hemisolvate, C14H11ClN2OS·0.5CH2Cl2, an anti disposition is found for the thione and ketone atoms, as well as the N-H H atoms; the dichloro-methane C atom lies on a twofold axis. The central chromophore (including the two adjacent ipso C atoms) is planar (r.m.s. deviation = 0.021 Å) owing to the presence of an intra-molecular N-H⋯O hydrogen bond, which closes an S(6) loop. Significant twists are evident in the mol-ecule, the dihedral angles between the central moiety and the phenyl and benzene rings being 29.52 (7) and 40.02 (7)°, respectively. In the crystal, eight-membered {⋯HNC= S}2 synthons with twofold symmetry form via N-H⋯S hydrogen bonds. The dimers are connected into a supra-molecular chain along [111] by C-H⋯O inter-actions. The chains stack along the c axis, forming columns which define channels in which the occluded dichloro-methane mol-ecules reside.

In the title salt, C(14)H(16)N(+)·Cl(-), the complete cation and complete anion are generated by the application of mirror symmetry. The mol-ecule is nonplanar, as seen in the dihedral angle between the terminal phenyl rings [70.92 (5)°]. In the crystal, N-H⋯Cl hydrogen bonds involving both aza-nium H atoms link the ions into a zigzag supra-molecular chain along [100].

A series of norephedrine-based Schiff bases (1a-6a and 1b-6b) were synthesized by reacting substituted salicylaldehydes with d-norephedrine or l-norephedrine. The structure of these compounds was confirmed by elemental analyses and spectroscopic techniques. The molecular structures of 5a and 6a have been determined by X-ray crystallography, which revealed that the compounds are in the oxoamino form, with bent intramolecular N-H···O (N···O ≈ 2.58 Å) hydrogen bonds and that they are associated in dimers bridged by linear intermolecular O-H···O (O···O ≈ 2.69 Å) hydrogen bonds. The density functional theory calculations on 5a confirmed that the oxoamino form is more stable than the phenolimino form by 12.2 kcal/mol. All the compounds were evaluated for their antibacterial activity using resazurin dye as indicator by twofold dilution method against four bacteria namely, Bacillus subtilis (NCIM2718), Staphylococcus aureus (NCIM5021), Escherichia coli (NCIM2931), and Proteus vulgaris (NCIM2813)., (© 2011 John Wiley & Sons A/S.)

The title salt, C(12)H(24)N(+)·NCS(-), represents a monoclinic polymorph of the previously reported ortho-rhom-bic form [Khawar Rauf et al. (2008 ▶). Acta Cryst. E64, o366]. Two independent formula units comprise the asymmetric unit with the major difference in their mol-ecular structures relating to the relative dispositions of the cyclo-hexyl rings [dihedral angles = 79.88 (6) and 67.72 (5)°]. Further, the independent anions form distinctive patterns of hydrogen-bonding inter-actions, i.e. 2 × N-H⋯N versus N-H⋯N and N-H⋯S. The resulting supra-molecular architecture is a supra-molecular chain along the c axis based on a square-wave topology.

The complex mol-ecule of the title complex, [Pd(C(16)H(23)N(2)OS)(2)], is completed by crystallographic twofold symmetry with the metal atom lying on the rotation axis. The Pd(II) atom exists within a slightly distorted square-planar geometry defined by a cis-O(2)S(2) donor set. The dihedral angle formed between the mean planes of the symmetry-related six-membered chelate rings is 12.88 (7)° and the bond lengths within the rings are indicative of significant electron delocalization. In the crystal, mol-ecules aggregate into dimers linked by four C-H⋯O inter-actions.

Two independent mol-ecules comprise the asymmetric unit of the title compound, C(14)H(20)N(2)OS. These differ in the relative orientations of the pentyl chains [C-C-C-C torsion angles = -176.7 (3) and 176.4 (3)°]. Significant twists are evident in each mol-ecule, the dihedral angles formed between the thio-urea and amide residues being 53.47 (17) and 55.81 (17)°. In the crystal, each mol-ecule self-associates via a centrosymmetric eight-membered {⋯HNC=S}(2) synthon, and these are connected into a supra-molecular chain along [110] via C-H⋯O contacts. Disorder is noted for one of the independent mol-ecules in that two orientations (50:50) were resolved for its benzene ring.

The Ni(II) atom in the title complex, [Ni(C(13)H(8)BrNOS)(C(18)H(15)P)], is coordinated by the N, O and S atoms of the dianionic tridentate ligand, and its square-planar geometry is completed by a phosphane P atom. The dihedral angle between the aromatic rings in the 4-bromo-2-[(2-sulfido-phen-yl)imino-meth-yl]phenolate ligand is 2.01 (14)°. The most prominent feature of the packing is the presence of supra-molecular chains aligned along the a axis, mediated by C-H⋯S inter-actions.

The title compound, C(16)H(24)N(2)OS, is twisted about the central N(H)-C bond with the C-N-C-S torsion angle being 119.6 (3)°. The carbonyl O and thione S atoms are directed to opposite sides of the mol-ecule, a conformation that allows for the formation of a linear supra-molecular chain comprising alternating eight-membered {⋯HNCS}(2) and 14-membered {⋯HCNCNCO}(2) synthons.

The title mol-ecule, C(16)H(24)N(2)OS, is twisted about the central N(H)-C bond with a C-N(H)-C-N torsion angle of -62.67 (15)°. The carbonyl group is twisted out of the plane of the benzene ring, forming a C-C-C=O torsion angle of -25.06 (17)°. In the crystal, mol-ecules related by centres of symmetry are linked by pairs of inter-molecular N-H⋯S hydrogen bonds, forming eight-membered {⋯HNCS}(2) synthons. These are further connected by weak via C-H⋯O contacts, forming a two-dimensional array in the bc plane.

Two independent thio-urea mol-ecules comprise the asymmetric unit of the title compound, C(22)H(20)N(2)OS. The central N-C(=S)N(H)C(=O) atoms in each mol-ecule are virtually superimposable and each is twisted [C-N-C-S torsion angles = 121.3 (3) and -62.3 (4)°]. The mol-ecules differ only in terms of the relative orientations of the benzyl benzene rings [major difference between the C-N-C-C torsion angles of -146.6 (3) and -132.9 (3)°]. The presence of N-H⋯S hydrogen bonding leads to the formation of supra-molecular chains along the a axis. These are consolidated in the crystal packing by C-H⋯O inter-actions. The crystal was found to be a combined non-merohedral and racemic twin (twin law 00/00/001), with the fractional contribution of the minor components being approximately 9 and 28%.

Two independent thio-urea derivatives comprise the asymmetric unit of the title compound, C(14)H(20)N(2)OS. The major difference between the mol-ecules relates to a twist in the relative orientation of the benzene rings [torsion angles = 4.5 (2) and -19.9 (2)° for the two independent mol-ecules]. The thio-carbonyl and carbonyl groups lie to opposite sides of the mol-ecule as there are twists about the central N-S bond [torsion angles = 83.90 (15) and 81.77 (15)°]. Supra-molecular chains extending parallel to [101] with a stepped topology and mediated by N-H⋯O hydrogen bonding feature in the crystal structure. C-H⋯O and C-H⋯π inter-actions are also present.