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1.  4-{2-[2-(4-Chloro­benzyl­idene)hydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-(4-meth­oxy­phen­yl)sydnone 
The title compound, C19H15ClN6O3S, exists in trans and cis configurations with respect to the acyclic C=N bonds. The 3,6-dihydro-2H-1,3,4-thia­diazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.013 (1) Å] and forms dihedral angles of 34.76 (4) and 48.67 (4)° with the benzene rings. An intra­molecular C—H⋯O hydrogen bond stabilizes the mol­ecular structure and forms an S(6) ring motif. In the crystal packing, inter­molecular N—H⋯N hydrogen bonds link centrosymmetrically related mol­ecules into dimers, generating R 2 2(8) ring motifs. The dimers are then linked into a three-dimensional network by inter­molecular C—H⋯O and C—H⋯Cl hydrogen bonds, and by C—H⋯π inter­actions. Further stabilization is provided by π–π inter­actions involving the sydnone rings, with centroid–centroid separations of 3.4198 (5) Å.
doi:10.1107/S1600536811013900
PMCID: PMC3089192  PMID: 21754480
2.  3-Methyl-5-oxo-4-(2-phenyl­hydrazinyl­idene)-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title compound, C11H11N5OS, the pyrazole ring is approximately planar, with a maximum deviation of 0.010 (2) Å. The dihedral angles between the benzene ring and the pyrazole and carbothio­amide groups are 5.42 (9) and 10.61 (18)°, respectively. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are connected by inter­molecular N—H⋯O and C—H⋯S hydrogen bonds, forming R 2 2(12) ring motifs. In addition, there is a π–π stacking inter­action [centroid–centroid distance = 3.5188 (11) Å] between the pyrazole and benzene rings. These inter­actions link the mol­ecules into infinite chains along [001].
doi:10.1107/S1600536811009779
PMCID: PMC3099837  PMID: 21754198
3.  (E)-6-Bromo-3-{2-[2-(4-chloro­benzyl­idene)hydrazin­yl]thia­zol-5-yl}-2H-chromen-2-one 
In the title compound, C19H11N3O2SClBr, the chromene ring system and the thia­zole ring are each approximately planar, with maximum deviations of 0.033 (3) Å and 0.006 (3) Å, respectively. The mol­ecule adopts an E configuration about the central C=N double bond. The central thia­zole ring makes dihedral angles of 9.06 (14)° and 12.07 (11)° with the chloro-substituted phenyl ring and the chromene ring, respectively. The mol­ecular structure features a short C—H⋯O contact, which generates an S(6) ring motif. The crystal structure is stabilized by inter­molecular N—H⋯O hydrogen bonds, which link the mol­ecules into chains along the b axis. π–π stacking inter­actions [centroid-centroid distance = 3.4813 (15) Å] are also present.
doi:10.1107/S1600536811011172
PMCID: PMC3099884  PMID: 21754027
4.  Ethyl 2-[2-(3-meth­oxy­phen­yl)hydrazinyl­idene]-3-oxobutano­ate 
The title compound, C13H16N2O4, is approximately planar (r.m.s. deviation = 0.065 Å for the 19 non-H atoms). An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif and the mol­ecule adopts an E conformation with respect to the central C=N double bond. In the crystal, pairs of inter­molecular C—H⋯O hydrogen bonds link adjacent mol­ecules into inversion dimers. The crystal structure also features weak C—H⋯π inter­actions.
doi:10.1107/S1600536811039444
PMCID: PMC3201266  PMID: 22065239
5.  2-{(E)-[(2Z)-2-(1,2-Di­hydro­phthalazin-1-yl­idene)hydrazinyl­idene]meth­yl}phenol 
The title compound, C15H12N4O, adopts an E conformation with respect to the azomethine bond and crystallizes in its hydrazinyl­idene tautomeric form. The dihedral angle between the ring systems is 15.98 (7)°. The phenol O—H group forms an intra­molecular O—H⋯N hydrogen bond. In the crystal, pairs of N—H⋯N and C—H⋯O hydrogen bonds link neighbouring mol­ecules into centrosymmetric dimers. These dimers are inter­connected by means of three types of π–π stacking inter­actions. One, with a centroid–centroid distance of 3.577 (1) Å [inter­planar separation = 3.4673 (6) Å], connects adjacent mol­ecules into centrosymmetric dimers. The other two inter­actions, on the outward facing sides of the dimers, are between phenol rings of neighboring mol­ecules [centroid–centroid separation = 3.7907 (13) Å and inter­planar separation = 3.5071 (8) Å], and between phthalazin units [centroid–centroid separation = 3.6001 (12) Å and inter­planar separation = 3.4891 (7) Å]. In combination, the π–π inter­actions lead to the formation of infinite layers with mol­ecules stacked along [0-11]. These layers are, in turn, connected with neighbouring layers through the N—H⋯N and C—H⋯O hydrogen bonds, yielding a three-dimensional supra­molecular architecture.
doi:10.1107/S1600536813024203
PMCID: PMC3790393  PMID: 24098212
6.  (E)-3-(2-{2-[1-(3-Hy­droxy­phen­yl)ethyl­idene]hydrazin­yl}-1,3-thia­zol-4-yl)-2H-chromen-2-one 
In the title compound, C20H15N3O3S, the thia­zole ring is approximately planar, with a maximum deviation of 0.003 (1) Å, and makes dihedral angles of 7.44 (6) and 1.88 (6)° with the hy­droxy-substituted phenyl ring and the pyran ring, respectively. The hydroxyl group is disordered over two sets of sites, with an occupancy ratio of 0.567 (3):0.433 (3). In the crystal, the major disorder component mol­ecules are connected via bifurcated (three-centre) O—H⋯O and C—H⋯O hydrogen bonds, generating R 1 2(6) motifs and resulting in supra­molecular chains along the a axis. In the minor occupancy component, however, mol­ecules are connected via C—H⋯O hydrogen bonds, forming supra­molecular chains along the b axis. Furthermore, the crystal structure is stabilized by π–π inter­actions between the thia­zole rings [centroid–centroid distance = 3.5476 (7) Å].
doi:10.1107/S1600536811012189
PMCID: PMC3089171  PMID: 21754396
7.  3-{2-[2-(2-Fluoro­benzyl­idene)hydrazin­yl]-1,3-thia­zol-4-yl}-2H-chromen-2-one 
In the title compound, C19H12FN3O2S, the chromene ring system and the thia­zole ring are approximately planar [maximum deviations of 0.023 (3) Å and 0.004 (2) Å, respectively]. The chromene ring system is inclined at angles of 4.78 (10) and 26.51 (10)° with respect to the thia­zole and benzene rings, respectively, while the thia­zole ring makes a dihedral angle of 23.07 (12)° with the benzene ring. The mol­ecular structure is stabilized by an intra­molecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. The crystal packing is consolidated by inter­molecular N—H⋯O hydrogen bonds, which link the mol­ecules into chains parallel to [100], and by C—H⋯π and π–π [centroid–centroid distance = 3.4954 (15) Å] stacking inter­actions.
doi:10.1107/S1600536810018647
PMCID: PMC2979535  PMID: 21579518
8.  6-Bromo-3-{2-[2-(diphenyl­methyl­ene)hydrazin­yl]-1,3-thia­zol-5-yl}-2H-chromen-2-one chloro­form monosolvate 
In the title compound, C25H16BrN3O2S·CHCl3, the thia­zole ring is approximately planar [maximum deviation = 0.002 (3) Å] and makes dihedral angles of 10.75 (14) and 87.75 (15)/2.80 (14)° with the pyran ring system and the two terminal phenyl rings, respectively. The solvent mol­ecule is disordered over two sets of sites, with refined occupancies of 0.639 (7) and 0.361 (7). In the crystal, mol­ecules are connected via pairs of weak C—H⋯O inter­actions, forming centrosymmetric dimers. An intra­molecular C—H⋯O hydrogen bond generates an S(6) ring motif.
doi:10.1107/S1600536811012335
PMCID: PMC3089344  PMID: 21754402
9.  Methyl 2-meth­oxy-4-{[2-(4-nitro­phen­yl)hydrazinyl­idene]meth­yl}benzoate 
The mol­ecule of the title Schiff base compound, C16H15N3O5, obtained from a condensation reaction of 4-acet­oxy-3-meth­oxy­benzaldehyde and 4-nitro­phenyl­hydrazine, adopts an E geometry with respect to the C=N double bond. The mol­ecule is roughly planar, with the two benzene rings twisted slightly with respect to each other by a dihedral angle of 6.90 (9)°. In the crystal, inter­molecular N—H⋯O hydrogen bonds link centrosymmetrically related pairs of mol­ecules, forming dimers of R 2 2(22) graph-set motif. The dimers are further connected through slipped π–π inter­actions between symmetry-related benzene rings [centroid–centroid distance of 3.646 (1) Å, offset angle of 15.4°].
doi:10.1107/S160053681003802X
PMCID: PMC2983317  PMID: 21587632
10.  2-{(E)-[(2Z)-(3-Chloro-1-methyl-2,2-di­oxo-3,4-dihydro-1H-2,1-benzo­thia­zin-4-yl­idene)hydrazinyl­idene]meth­yl}phenol 
In the title compound, C16H14ClN3O3S, the thia­zine ring adopts a sofa (half-chair) conformation, with an r.m.s. deviation from the mean plane of 0.23 Å. The S atom and S-bonded C atom exhibit the maximum deviations from the thia­zine mean plane [−0.3976 (12) and 0.3179 (14) Å, respectively]. The conformations around the double bonds in the R 2C=N—N=CHR unit are Z and E. An intra­molecular O—H⋯N hydrogen bond with the hy­droxy group as donor generates an S(6) ring motif. In the crystal, pairs of weak C—H⋯O inter­actions connect the mol­ecules, forming inversion dimers.
doi:10.1107/S1600536811055978
PMCID: PMC3275000  PMID: 22346945
11.  3-{2-[2-(Diphenyl­methyl­ene)hydrazin­yl]thia­zol-4-yl}-2H-chromen-2-one 
In the title compound, C25H17N3O2S, the coumarin ring system is essentially planar with a maximum deviation of 0.019 (2) Å. A weak intra­molecular C—H⋯O hydrogen bond stabilizes the mol­ecular structure, so that the coumarin plane is approximately coplanar with the thia­zole ring, making a dihedral angle of 2.5 (10)°. The two phenyl rings are nearly perpendicular to each other, with a dihedral angle of 81.44 (12)°. In the crystal structure, the mol­ecules are linked into an infinite chain along the b axis by inter­molecular C—H⋯O hydrogen bonds. Weak C—H⋯π inter­actions are observed between the chains.
doi:10.1107/S1600536810023627
PMCID: PMC3007000  PMID: 21587999
12.  (E)-6-Bromo-3-{2-[2-(2-chloro­benzyl­idene)hydrazin­yl]thia­zol-5-yl}-2H-chromen-2-one dimethyl sulfoxide monosolvate 
In the title compound C19H11N3O2SClBr·C2H6OS, the mol­ecule adopts an E configuration about the central C=N double bond. The chromene ring system and the thia­zole ring are approximately planar, with maximum deviations of 0.027 (2) and 0.003 (1) Å, respectively. The central thia­zole ring makes dihedral angles of 21.82 (9) and 5.88 (7)° with the chloro-substituted phenyl ring and the chromene ring, respectively. In the crystal, mol­ecules are connected via N—H⋯O, N—H⋯S and C—H⋯O hydrogen bonds, forming supra­molecular chains along the c axis. An intra­molecular C—H⋯O hydrogen bond occurs. π–π inter­actions are observed between the thia­zole and phenyl rings [centroid–centroid distance = 3.6293 (10) Å]. A short Br⋯Cl contact of 3.37 (6) Å also occurs.
doi:10.1107/S1600536811011160
PMCID: PMC3100073  PMID: 21754028
13.  4-[2-(4-Bromo­phen­yl)hydrazinyl­idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title compound, C11H10BrN5OS, the approximately planar pyrazole ring [maximum deviation = 0.014 (2) Å] forms a dihedral angle of 5.49 (13)° with the benzene ring. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked through inter­molecular N—H⋯S and N—H⋯O hydrogen bonds, forming a two-dimensional network parallel to (100). A short Br⋯Br contact of 3.5114 (6) Å is also observed.
doi:10.1107/S1600536811034726
PMCID: PMC3201347  PMID: 22064818
14.  3-Chloro-6-[(E)-2-(1-phenyl­ethyl­idene)hydrazin­yl]pyridazine 
Two independent mol­ecules are present in the asymmetric unit of the title compound, C12H11ClN4, (Z′ = 2): the dihedral angles between the phenyl and pyridizine rings are 8.35 (10) and 37.64 (6)°. In the crystal, the two mol­ecules form inversion dimers with R 2 2(8) ring motifs through inter­molecular N—H⋯N hydrogen bonds. The crystal structure is stabilized by π–π inter­actions between the pyridazine rings of symmetry-related molecules. In one of the independent mol­ecules, the centroid–centroid separations are 3.6927 (13) and 3.7961 (13) Å, whereas in the other, the separations are 3.6909 (13) and 3.9059 (13) Å.
doi:10.1107/S1600536810024402
PMCID: PMC3007326  PMID: 21588398
15.  1-Isobutyl-4-meth­oxy-1H-imidazo[4,5-c]quinoline 
In the title compound, C15H17N3O, the 1H-imidazo[4,5-c]quinoline ring system is approximately planar, with a maximum deviation of 0.036 (1) Å. The C—N—C—C torsion angles formed between this ring system and the isobutyl unit are −99.77 (16) and 79.71 (17)°. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into chains along the c axis.
doi:10.1107/S1600536811031801
PMCID: PMC3200859  PMID: 22058955
16.  4-{2-[2-(4-Chloro­benzyl­idene)hydrazinyl­idene]-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl}-3-phenyl­sydnone 
The title compound, C18H13ClN6O2S, exists in trans and cis configurations with respect to the acyclic C=N bonds [C=N = 1.2837 (15) and 1.3000 (14) Å, respectively]. The 3,6-dihydro-2H-1,3,4-thia­diazine ring adopts a half-boat conformation. The sydnone ring is approximately planar [maximum deviation = 0.002 (1) Å] and forms dihedral angles of 50.45 (7) and 61.21 (6)° with the aromatic rings. In the crystal, inter­molecular N—H⋯N, C—H⋯Cl and C—H⋯S hydrogen bonds link the mol­ecules into layers parallel to ab plane. The crystal packing is stabilized by C—H⋯π inter­actions and further consolidated by π–π inter­actions involving the phenyl rings [centroid–centroid distance = 3.6306 (7) Å].
doi:10.1107/S1600536811013912
PMCID: PMC3089094  PMID: 21754481
17.  4-[2-(4-Chloro­phen­yl)hydrazinyl­idene]-3-methyl-1H-pyrazol-5(4H)-one 
In the title compound, C10H9ClN4O, the pyrazole ring [maximum deviation = 0.014 (2) Å] forms a dihedral angle of 7.06 (14)° with the chloro­benzene ring. The mol­ecular conformation is stabilized by an intra­molecular N—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R 2 2(16) ring motifs. The dimers are further connected by N—H⋯N hydrogen bonds, thereby forming layers lying parallel to the bc plane.
doi:10.1107/S1600536811037020
PMCID: PMC3201479  PMID: 22058782
18.  1-(2-Meth­oxy­phen­yl)-2-{[2-(2-meth­oxy­phen­yl)hydrazinyl­idene](nitro)­meth­yl}diazene 
In the title compound, C15H15N5O4, a nitro­formazan derivative, the formazan unit is essentially planar with an r.m.s. deviation of 0.0204 (6) Å and adopts a closed syn,s-cis configuration with an intra­molecular N—H⋯N hydrogen bond. The formazan plane makes dihedral angles of 4.32 (5) and 24.35 (5)° with the benzene rings. The dihedral angle between the formazan plane and the nitro group is 12.58 (8)°. In the crystal, C—H⋯O inter­actions connect the mol­ecules into an inversion dimer.
doi:10.1107/S1600536812004175
PMCID: PMC3295411  PMID: 22412522
19.  (Z)-3-Hydrazinyl­idene-1-phenyl­indolin-2-one 
The indoline fused-ring system of the title Schiff base, C14H11N3O, is planar (r.m.s. deviation = 0.005 Å); the phenyl substituent is aligned at 66.5 (1)° with respect to the ring system. The amino –NH2 unit forms an intra­molecular hydrogen bond with the carbonyl O atom. Mol­ecules are connected by an inter­molecular N—H⋯N hydrogen bond, generating a zigzag chain that runs along the short c axis of the unit cell.
doi:10.1107/S1600536810043916
PMCID: PMC3009040  PMID: 21589173
20.  6-Bromo-1-methyl-4-[2-(4-methyl­benzyl­idene)hydrazinyl­idene]-3H-2λ6,1-benzothia­zine-2,2-dione 
In the title compound, C17H16BrN3O2S, the two fused rings are twisted by a dihedral angle of 6.61 (15)°. The thia­zine ring adopts a sofa conformation. The toluene ring is oriented at dihedral angles of 15.5 (2) and 20.6 (2)° with respect to the bromo­benzene and thia­zine rings, respectively. The benzyl­idene system is approximately planar [r.m.s. deviation = 0.0388 Å]. In the cyrstal, weak inter­molecular C—H⋯O hydrogen bonds connects the mol­ecules into a chain along the b axis.
doi:10.1107/S1600536811028406
PMCID: PMC3213534  PMID: 22091111
21.  (E)-3-Methyl-4-[(2-oxidoquinolin-1-ium-3-yl)methyl­eneamino]-1H-1,2,4-triazole-5(4H)-thione N,N-dimethyl­formamide solvate 
The title 1,2,4-triazole compound, C13H11N5OS·C3H7NO, crystallizes as a 1:1 dimethyl­formamide (DMF) solvate. The main mol­ecule exists in a trans configuration with respect to the acyclic C=N bond. An intra­molecular C—H⋯S hydrogen bond generates an S(6) ring motif. In the synthesis, a proton is transferred from the O atom of a hydr­oxy group to the quinoline group N atom. The essentially planar triazole ring and quinoline ring system [maximum deviations of 0.001 (2) and 0.013 (2) Å, respectively] form a dihedral angle of 5.86 (9)°. In the crystal structure, mol­ecules of (E)-4-[(2-hydroxy-3-­quinolyl)methyl­eneamino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione are linked into R 2 2(8) centrosymmteric dimers via N—H⋯O hydrogen bonds. These dimers are further linked into an extended three-dimensional structure by the DMF solvent mol­ecules via inter­molecular N—H⋯O and C—H⋯O hydrogen bonds. The crystal structure is consolidated by two different inter­molecular π–π inter­actions [centroid–centroid distances = 3.6593 (12) and 3.6892 (12) Å].
doi:10.1107/S1600536809050090
PMCID: PMC2972175  PMID: 21578940
22.  (E)-6-Bromo-3-{2-[2-(2-meth­oxy­benzyl­idene)hydrazin­yl]-1,3-thia­zol-4-yl}-2H-chromen-2-one 
In the title compound, C20H14BrN3O3S, the mol­ecule adopts an E configuration about the central C=N double bond. The chromene ring system and the thia­zole ring are approximately planar [maximum deviations = 0.029 (3) and 0.007 (3) Å, respectively]. The chromene ring system is inclined at angles of 7.37 (12) and 13.90 (13)° with respect to the thia­zole and benzene rings, respectively, while the thia­zole ring makes a dihedral angle of 12.58 (15)° with the benzene ring. In the crystal, mol­ecules are connected by N—H⋯O hydrogen bonds, forming C(8) supra­molecular chains along the c axis.
doi:10.1107/S1600536811024536
PMCID: PMC3152023  PMID: 21837193
23.  4-Meth­oxy­quinolinium-2-carboxyl­ate dihydrate 
The title hydrated quinoline derivative, C11H9NO3·2H2O, crystallizes as a zwitterion in which the quinoline N atom is protonated. The quinoline ring is essentially planar, with a maximum deviation of 0.017 (2) Å. An intra­molecular N—H⋯O hydrogen bond between the protonated N atom and the O atom of the carboxyl­ate group in the zwitterion forms an S(5) ring motif. In the crystal, the zwitterions are connected into inversion dimers via pairs of N—H⋯O and C—H⋯O hydrogen bonds with R 2 2(4) and R 1 2(6) motifs. The water mol­ecules are connected via O—H⋯O hydrogen bonds, forming supra­molecular chains along the c axis. Furthermore, the chains and the dimers are connected via O—H⋯O hydrogen bonds, forming ladder-like supra­molecular ribbons along the c axis.
doi:10.1107/S1600536811001541
PMCID: PMC3051487  PMID: 21523101
24.  (E)-4-(4-Hydr­oxy-3-methoxy­benzyl­idene­amino)-3-[1-(4-isobutyl­phen­yl)eth­yl]-1H-1,2,4-triazole-5(4H)-thione 
The asymmetric unit of the title compound, C22H26N4O2S, contains two crystallographically independent mol­ecules (A and B). The isobutyl unit of mol­ecule B is disordered over two orientations with refined occupancies of 0.785 (6) and 0.215 (6). In each mol­ecule, intra­molecular C—H⋯S hydrogen bonds generate S(6) ring motifs. The essentially planar 1,2,4-triazole rings [r.m.s. deviations of 0.004 (2) and 0.011 (2) Å, in A and B respectively] form dihedral angles of 85.86 (12), 8.38 (10)°, respectively, with the isobutyl-substituted phenyl ring and the 2-methoxy­phenol substituent in mol­ecule A [89.26 (13) and 2.46 (10)°, respectively, in B]. In the crystal structure, inter­molecular N—H⋯N and N—H⋯S hydrogen bonds link neighbouring mol­ecules, generating R 2 2(7) ring motifs. These molecules are further inter­connected into extended chains along [20] by inter­molecular O—H⋯O hydrogen bonds. The crystal structure is further stabilized by π–π [centroid-centroid distance = 3.6299 (13) Å] and C—H⋯π inter­actions. A short O⋯O contact of 2.781 (2) Å is also observed.
doi:10.1107/S160053680905209X
PMCID: PMC2980163  PMID: 21580185
25.  4-{[2-(2,4-Dinitro­phen­yl)hydrazinyl­idene]meth­yl}phenol ethanol hemisolvate 
In the title compound, C13H10N4O5·0.5C2H5OH, the two benzene rings form a dihedral angle of 4.29 (9)°. The ethanol solvent mol­ecule was treated as disordered between two orientations related by symmetry (center of inversion), with occupancies fixed at 0.5. The crystal packing, stabilized by inter­molecular O—H⋯O and N—H⋯O hydrogen bonds and π–π inter­actions [indicated by the short distance of 3.7299 (7) Å between the centroids of benzene rings from neighbouring mol­ecules], exhibits short inter­molecular O⋯O contacts of 2.8226 (3) Å.
doi:10.1107/S1600536810045782
PMCID: PMC3011783  PMID: 21589441

Results 1-25 (349172)