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1.  (Z)-2-(5-Chloro-2-oxoindolin-3-yl­idene)-N-methyl­hydrazinecarbothio­amide 
In the title compound, C10H9ClN4OS, an intra­molecular N—H⋯O hydrogen-bonding inter­action and an N—H⋯N inter­action generate ring motifs [graph sets S(6) and S(5), respectively]. In the crystal, mol­ecules form a chain through N—H⋯O hydrogen bonds, and these are extended by N—H⋯S hydrogen-bonding inter­actions into an infinite three-dimensional network. The crystal structure also exhibits weak C—H⋯π inter­actions.
doi:10.1107/S1600536812007386
PMCID: PMC3354764  PMID: 22606200
2.  Bis{2-[3-(hy­droxy­imino-κN)butan-2-yl­idene]-N-methyl­hydrazinecarbothio­amide-κ2 N 2,S}nickel(II) dichloride 
The asymmetric unit of the title compound, [Ni(C6H12N4OS)2]Cl2, contains two independent NiII complex cations and four chloride anions. Each NiII ion is six-coordinated in a distorted octa­hedral geometry by four N atoms from the two imine and two oxime groups and two S atoms from the thione group. In the crystal, the cations and anions are linked through N—H⋯Cl and O—H⋯Cl hydrogen bonds into infinite chains propagating along [10]. Weak inter­molecular C—H⋯O and C—H⋯Cl hydrogen bonds are also observed.
doi:10.1107/S1600536811055395
PMCID: PMC3274853  PMID: 22346800
3.  2-[(E)-2-Hy­droxy-3-methoxy­benzyl­idene]-N-methyl­hydrazinecarbothio­amide 
In the crystal structure of the title compound, C11H15N3O2S, mol­ecules are linked by pairs of N—H⋯O and O—H⋯S hydrogen, forming inversion dimers. These dimers are linked by N—H⋯S hydrogen bonds, forming double-stranded chains propagating along the b-axis direction. The two C atoms of the end chain of the mol­ecule are disordered over two sets os sites [occupancy ratio 0.574 (9):0.426 (9)].
doi:10.1107/S1600536812049847
PMCID: PMC3588310  PMID: 23476442
4.  2-[1-(2-Hy­droxy-6-meth­oxy­phen­yl)ethyl­idene]-N-methyl­hydrazinecarbothio­amide acetonitrile monosolvate 
In the title compound, C11H15N3O2S·C2H3N, the dihedral angle between the benzene ring and the mean plane of the hydrazinecarbothio­amide group is 75.1 (2)°. In the crystal, the main mol­ecule is linked to the solvent mol­ecule by a weak N—H⋯N hydrogen bond while O—H⋯S hydrogen bonds link the mol­ecules into columns along [100].
doi:10.1107/S1600536812048799
PMCID: PMC3588304  PMID: 23476372
5.  (Z)-2-(5-Chloro-2-oxoindolin-3-yl­idene)-N-phenyl­hydrazinecarbothio­amide 
In the title compound, C15H11ClN4OS, the dihedral angle between the nine-membered 5-chloro­indolin-2-one ring system and the benzene ring is 10.00 (6)°. Intra­molecular cyclic N—H⋯O and C—H⋯S hydrogen-bonding inter­actions [graph set S(6)] are present in the N—N—C—N chain between the ring systems. In the crystal, mol­ecules form centrosymmetric cyclic dimers through inter­molecular N—H⋯O hydrogen bonds [graph-set R 2 2(8)] and are extended by C—H⋯Cl inter­actions into infinite chains which propagate along [100].
doi:10.1107/S1600536811044199
PMCID: PMC3238816  PMID: 22199669
6.  (Z)-N-Methyl-2-(5-methyl-2-oxoindolin-3-yl­idene)hydrazinecarbothio­amide 
In the title compound, C11H12N4OS, an intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the mol­ecules form a helical chain along the a axis through an N—H⋯O hydrogen bond. These chains are extended by an N—H⋯S hydrogen bond and a C—H⋯π inter­action into a three-dimensional network.
doi:10.1107/S1600536812005417
PMCID: PMC3343935  PMID: 22590016
7.  (Z)-2-(5-Methyl-2-oxoindolin-3-yl­idene)-N-phenyl­hydrazinecarbothio­amide 
In the title compound, C16H14N4OS, the dihedral angle between the nine-membered 5-methyl­indolin-2-one ring system and the benzene ring is 10.21 (7)°. Intra­molecular cyclic N—H⋯O and C—H⋯S hydrogen-bonding inter­actions [graph set S(6)] are present within the N—N—C—N chain between the ring systems. In the crystal, mol­ecules form centrosymmetric cyclic dimers through pairs of N—H⋯O hydrogen bonds [graph set R 2 2(8)].
doi:10.1107/S1600536811049154
PMCID: PMC3239102  PMID: 22199950
8.  (Z)-N-Methyl-2-(5-nitro-2-oxoindolin-3-yl­idene)hydrazinecarbothio­amide 
In the title compound, C10H9N5O3S, an intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked via N—H⋯S hydrogen bonds into a zigzag chain along the b axis. C—H⋯O inter­actions are observed between the chains.
doi:10.1107/S1600536812001183
PMCID: PMC3343934  PMID: 22590015
9.  (E)-2-(4-Benz­yloxy-2-hy­droxy­benzyl­idene)-N-methyl­hydrazinecarbo­thio­amide 
The mol­ecule of the title compound, C16H17N3O2S, adopts an E conformation with respect to the azomethine C=N bond. The hydrazinecarbo­thio­amide fragment is close to planar, with a largest deviation from the least-squares plane of 0.079 (2) Å for the hydrazide N atom. This fragment forms a dihedral angle of 9.43 (9)° with the central benzene ring. The benzene rings are inclined to one another by 67.55 (12)°. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond involving the azomethine N atom. In the crystal, mol­ecules are linked through weak N—H⋯S and N—H⋯O hydrogen bonds into double ribbons along [010]. The crystal packing also features C—H⋯π inter­actions.
doi:10.1107/S1600536813034892
PMCID: PMC3998281  PMID: 24764842
10.  2-[1-(2-Hy­droxy-4-meth­oxy­phen­yl)ethyl­idene]-N-methyl­hydrazinecarbo­thio­amide 
In the title compound, C11H15N3O2S, the dihedral angle between the mean planes of the benzene ring and hydrazinecarbo­thio­amide group is 9.2 (1)°. An intra­molecular O—H⋯N hydrogen bond is observed, serving to maintain an approximately planar conformation for the molecule. In the crystal, inversion dimers linked by C—H⋯O inter­actions occur. Further C—H⋯O contacts link dimers into (010) chains.
doi:10.1107/S1600536813019831
PMCID: PMC3793802  PMID: 24109389
11.  (Z)-2-(5-Fluoro-2-oxoindolin-3-yl­idene)-N-phenyl­hydrazinecarbothio­amide 
The title compound, C15H11FN4OS, crystallizes with three independent mol­ecules (A, B and C) in the asymmetric unit. The dihedral angles between the nine-membered 5-fluoro­indolin-2-one ring system and the benzene ring are 22.14 (11), 12.56 (11) and 3.70 (11)° in mol­ecules A, B and C, respectively. In all three mol­ecules, intra­molecular cyclic N—H⋯O and C—H⋯S hydrogen-bonding inter­actions [graph set S(6)] are present in the N—N—C—N chain between the ring systems. In the crystal, the A mol­ecules form centrosymmetric cyclic dimers through inter­molecular N—H⋯O hydrogen bonds, which are linked into a supramolecular chain along [100] via C—H⋯F interactions; each type of hydrogen bond has graph set graph set R 2 2(8). A similar chain stabilised by similar interactions and also along [100] but, comprising alternating molecules of B and C is found. The latter chains are connected via C—H⋯S interactions, forming a layer with a zigzag topology parallel to (001).
doi:10.1107/S160053681105433X
PMCID: PMC3274981  PMID: 22346926
12.  Bis{N-ethyl-2-[3-(hy­droxy­imino-κN)butan-2-yl­idene]hydrazinecarbothio­amide-κ2 N 2,S}nickel(II) dichloride 
In the title complex, [Ni(C7H14N4OS)2]Cl2, the NiII ion is six-coordinated in a distorted octa­hedral geometry by four N atoms from the two imine and two oxime groups, and two S atoms from the thione groups. Two chloride ions complete the asymmetric unit. In the crystal, mol­ecules are linked through N—H⋯Cl and O—H⋯Cl hydrogen bonds into an infinite chain propagating along [101].
doi:10.1107/S1600536811055383
PMCID: PMC3274909  PMID: 22346856
13.  (E)-N-Ethyl-2-[(E)-3-(hy­droxy­imino)­butan-2-yl­idene]hydrazinecarbothio­amide 
In the crystal structure of the title compound, C7H14N4OS, mol­ecules are linked through N—H⋯S and O—H⋯N hydrogen bonds and C—H⋯S interactions, forming chains propagating along [21-1].
doi:10.1107/S1600536812028632
PMCID: PMC3414996  PMID: 22904983
14.  Ethyl 2-[2-(4-hy­droxy-3-meth­oxy­benzyl­idene)hydrazin-1-yl­idene]-3,4-dimethyl-2,3-dihydro-1,3-thia­zole-5-carboxyl­ate 
The title compound, C16H19N3O4S, is almost planar, with a dihedral angle of 2.88 (9)° between the mean planes of the benzene and thia­zole rings. The mol­ecule adopts an E conformation about the two C=N bonds, with a C—N—N—C torsion angle of −177.01 (11)°. An intra­molecular C—H⋯O hydrogen bond exists between a thia­zole methyl group and the formic acid ethyl ester carbonyl O atom. In the crystal, mol­ecules are linked by O—-H⋯O hydrogen bonds, forming chains propagating along [2-10]. The chains are linked via C—H⋯O hydrogen bonds with R 2 2(12) ring motifs, forming sheets lying parallel to (12-2). The sheets are further linked through out-of-plane C—H⋯N hydrogen bonds with R 2 2(12) ring motifs and C—H⋯π inter­actions, forming an inter­esting three-dimensional supra­molecular architecture.
doi:10.1107/S1600536812043772
PMCID: PMC3515300  PMID: 23284520
15.  2-(1,2,3,4-Tetra­hydro­naphthalen-1-yl­idene)hydrazinecarbothio­amide 
The mol­ecular structure of the title compound, C11H13N3S, is not planar: the maximum deviation from the mean plane of the non-H atoms is 0.521 (2) Å for an aliphatic C atom, which corresponds to an envelope conformation for the non-aromatic ring. The hydrazinecarbothio­amide substituent and the benzene ring have maximum deviations from the mean planes through the non-H atoms of 0.0288 (16) and 0.0124 (27) Å, respectively, and the dihedral angle between the two planes is 8.84 (13)°. In the crystal, mol­ecules are linked into chains along [10] by pairs of N—H⋯S hydrogen bonds between mol­ecules related by centres of symmetry.
doi:10.1107/S1600536812033302
PMCID: PMC3415020  PMID: 22905007
16.  (Z)-N-Ethyl-2-(5-fluoro-2-oxoindolin-3-yl­idene)hydrazinecarbothio­amide 
In the title compound, C11H11FN4OS, an intra­molecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol­ecules form chains through N—H⋯O hydrogen bonds, which are extended by N—H⋯S hydrogen bonds into an infinite three-dimensional network.
doi:10.1107/S1600536812036471
PMCID: PMC3470224  PMID: 23125668
17.  (2Z)-N-(2-Chloro­benz­yl)-2-(2-oxo-2,3-dihydro-1H-indol-3-yl­idene)hydrazinecarbothio­amide 
In the title compound, C16H13ClN4OS, the isatin ring system is oriented at dihedral angles of 10.60 (7) and 72.60 (3)° with respect to the thio­semicarbazide and 2-chloro­benzyl groups, respectively. The near planarity of the isatin and thio­semicarbazide groups [r.m.s. deviations of 0.0420 and 0.0163 Å, respectively] is reinforced by intra­molecular N—H⋯O and N—H⋯N hydrogen bonds, which generate S(6) and S(5) rings, respectively. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R 2 2(8) loops. Aromatic π–π stacking inter­actions between the centroids of heterocyclic five-membered and benzene rings [distance = 3.6866 (11) Å] are also observed.
doi:10.1107/S1600536812035076
PMCID: PMC3435743  PMID: 22969614
18.  N-Ethyl-2-[1-(2-hy­droxy-6-meth­oxy­phenyl)ethyl­idene]hydrazinecarbothio­amide 
In the title compound, C12H17N3O2S, the dihedral angle between the mean planes of the hydrazinecarbothio­amide group and the benzene ring is 86.8 (4)°. In the crystal, inter­molecular O—H⋯S hydrogen bonds link the mol­ecules into chains along [001]. The crystal studied was an inversion twin, the refined ratio of the twin components being 0.98021 (3):0.01978 (7).
doi:10.1107/S1600536812039323
PMCID: PMC3470346  PMID: 23125759
19.  Crystal structure of (Z)-N′-[1-(3-methyl-5-oxo-1-phenyl-1,5-di­hydro-4H-pyrazol-4-yl­idene)prop­yl]benzene­sulfono­hydrazide 
The title compound crystallizes in the keto form and the carbonyl O atom forms an intra­molecular N—H⋯O hydrogen bond with the neighbouring NH group. In the crystal, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds to form inversion dimers, which are linked via pairs of C—H⋯O hydrogen bonds, forming chains propagating along [100].
The title compound, C19H20N4O3S, was synthesized by refluxing equimolar amounts of 1-phenyl-3-methyl-4-propionylpyrazol-5-one and benzene­sulfonyl hydrazide in ethanol. The compound crystallizes in the keto form and the carbonyl O atom forms an intra­molecular N—H⋯O hydrogen bond with the neighbouring NH group. There is also C—H⋯O short contact involving the neighbouring phenyl ring. Probably as a result of this, the phenyl ring is inclined to the pyrazolone ring by only 7.58 (12)°. The dihedral angle between the phenyl ring and the benzene­sulfonyl ring is 22.78 (11)°. In the crystal, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers with an R 2 2(14) ring motif. The dimers are linked via pairs of C—H⋯O hydrogen bonds, forming chains propagating along [100].
doi:10.1107/S2056989015007094
PMCID: PMC4420066  PMID: 25995862
crystal structure; pyrazolone derivative; hydrogen bonding; polymer chain
20.  (E)-2-(4-Benz­yloxy-2-hy­droxy­benzyl­idene)-N-phenyl­hydrazinecarbothio­amide 
The title compound, C21H19N3O2S, exists in the thione form. The configuration about the C=N bond is E. The hydrazinecarbothio­amide unit adopts an almost planar arrangement, with maximum deviations of 0.016 (3) and −0.016 (2) Å for the two thio­urea N atoms. An intra­molecular O—H⋯N hydrogen bond occurs. Weak inter­molecular N—H⋯S, C—H⋯O and C—H⋯π inter­actions are observed in the crystal structure.
doi:10.1107/S1600536811049658
PMCID: PMC3239056  PMID: 22199904
21.  N′-[(1E,2E)-1-(2-Phenyl­hydrazin-1-yl­idene)-1-(phenyl­sulfon­yl)propan-2-yl­idene]benzohydrazide 
The configuration about each C=N bond in the title compound, C22H20N4O3S, is E. While to a first approximation the phenyl­hydrazin-1-yl­idene and benzohydrazide residues are coplanar, in part due to the presence of an intra­molecular N—H⋯N hydrogen bond, significant twists are evident in the orientations of the hydrazine [N—N—C—C torsion angle = −170.74 (11)°] and benzoyl benzene [N—C—C—C = −21.72 (18)°] rings. The sulfonyl benzene ring occupies a position almost normal to the rest of the mol­ecule [C—S—C—N = −92.28 (10)°]. Centrosymmetric aggregates mediated by pairs of hydrazide–sulfonyl N—H⋯O hydrogen bonds are the predominant packing motif in the crystal. These are connected into linear supra­molecular chains via C—H⋯O inter­actions which are, in turn, linked into layers in the ac plane via C—H⋯π inter­actions. Connections between layers along the b-axis direction are of the π–π type and occur between centrosymmetrically related hydrazine-bound benzene rings [centroid–centroid separation = 3.7425 (9) Å].
doi:10.1107/S1600536811031953
PMCID: PMC3200681  PMID: 22058945
22.  (E)-2-[1-(1-Benzothio­phen-3-yl)ethyl­idene]hydrazinecarbothio­amide methanol hemisolvate 
The asymmetric unit of the title compound, C11H11N3S2·0.5CH4O, contains four thio­semicarbazone mol­ecules and two methanol solvent mol­ecules. Each hydrazinecarbothio­amide mol­ecule adopts an E configuration with respect to the C=N double bond and is stabilized by an intra­molecular N—H⋯N hydrogen bond, resulting in an S(5) ring motif. In the crystal structure, an extensive network of N—H⋯O, N—H⋯N, O—H⋯S and N—H⋯S hydrogen bonds and weak C—H⋯O, C—H⋯N and C—H⋯S contacts together with an S⋯S [3.5958 (14) Å] and a C—H⋯π inter­action form a three-dimensional network.
doi:10.1107/S160053680801297X
PMCID: PMC2961618  PMID: 21202547
23.  2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)-2-cyano­acetamide 
Reaction of 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)propane­dial with hydroxyl­amine gives the title compound, C14H14ClN3O, in which the ring N atom is essentially planar [sum of angles around the ring N atom = 361°], indicating conjugation with the 2-cyano­acryl­amide unit. The orientation of the acetamide group arises from intra­molecular hydrogen bonding between the indole N—H and carbonyl groups. In the crystal, inversion-related acetamide groups form N—H⋯O hydrogen-bonded dimers in graph-set R 2 2(8) motifs, whilst dimers are also formed by pairs of amine–nitrile N—H⋯N hydrogen bonds in R 2 2(12) motifs. These inter­actions together generate ribbons that propagate along the b-axis direction.
doi:10.1107/S1600536811053918
PMCID: PMC3254566  PMID: 22259516
24.  (2E)-N-Methyl-2-[(2E)-3-phenyl­prop-2-en-1-yl­idene]hydrazinecarbothio­amide 
The title compound, C11H13N3S, is close to being planar, with a dihedral angle of 9.64 (3)° between the benzene ring and the thio­semicarbazone mean plane, maintained by the presence of π-conjugation in the chain linking the the two systems. In the crystal, N—H⋯S hydrogen bonds form centrosymmetric dimers through a cyclic association [graph-set R 2 2(8)].
doi:10.1107/S1600536812037397
PMCID: PMC3470202  PMID: 23125646
25.  Crystal structure of ethyl 2-(2-{(1E)-[(E)-2-(2-hy­droxy­benzyl­idene)hydrazin-1-yl­idene]meth­yl}phen­oxy)acetate 
In the title compound, C18H18N2O4, the planes of the benzene rings are twisted with respect to each other at 27.25 (7)°. The mol­ecule displays an extended conformation with an intra­molecular O—H⋯N hydrogen bond. In the crystal, weak C—H⋯O inter­actions link the mol­ecules, forming supra­molecular chains running along the b-axis direction.
doi:10.1107/S2056989014027273
PMCID: PMC4384580  PMID: 25878876
crystal structure; Schiff base ligand; hydrogen bonding

Results 1-25 (371589)