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1.  1,2-Diphenyl-2-(m-tolyl­amino)ethanone1  
The title compound, C21H19NO, belongs to the family of α-amino­ketones. The structure contains three benzene rings, two of which [the phenyl ring in the 1-position (B) and the methylaniline ring (A)] are nearly coplanar [dihedral angle = 5.4 (1)°], whereas the phenyl ring in the 2-position (C) is nearly normal to them [dihedral angles = 81.8 (1) and 87.0 (1)° for A/C and B/C, respectively]. The conformation of the N—H bond is syn to the C=O bond, favouring the formation of a centrosymmetric dimer of mol­ecules in the crystal structure. The mol­ecular packing is consolidated by this N—H⋯O hydrogen-bonding network.
doi:10.1107/S1600536810013371
PMCID: PMC2979094  PMID: 21579159
2.  Tetra-μ-acetato-κ8 O:O′-bis­{[2-(m-tolyl­amino)pyridine-κN]copper(II)} 
In the crystal structure of the title compound, [Cu2(C2H3O2)4(C12H12N2)2], the binuclear mol­ecule lies about a center of inversion; the four acetate groups each bridge a pair of CuII atoms. The coordination of the metal atom is distorted square-pyramidal, with the bonding O atoms comprising a square basal plane and the coordinating N atom of the N-heterocycle occupying the apical position. The pyridine ring is twisted with respect to the benzene ring at a dihedral angle of 45.68 (16)°. Intra­molecular N—H⋯O hydrogen bonding is present between the imino and carb­oxy groups.
doi:10.1107/S1600536809050041
PMCID: PMC2972063  PMID: 21578695
3.  Crystal structure of (Z)-1-(3,4-dichlorophenyl)-3-methyl-4-[(naphthalen-1-yl­amino)(p-tolyl)methylidene]-1H-pyrazol-5(4H)-one 
The title Schiff base compound, C28H21Cl2N3O, was synthesized by the condensation of 1-(3,4-di­chloro­phen­yl)-3-methyl-4-(4-methyl­benzo­yl)-1H-pyrazol-5(4H)-one with 1-aminona­phthalene. The p-tolyl ring is normal to the pyrazole ring, with a dihedral angle of 88.02 (14)°, and inclined to the naphthalene ring system by 78.60 (12)°. The pyrazole ring is inclined to the naphthalene ring system and the di­chloro-substituted benzene ring by 63.30 (12) and 11.03 (13)°, respectively. The amino group and carbonyl oxygen atom are involved in an intra­molecular N—H⋯O hydrogen bond enclosing an S(6) ring motif. There is also a short C—H⋯O contact involving the carbonyl O atom and the adjacent benzene ring. In the crystal, mol­ecules are linked by C—H⋯π inter­actions, forming a three-dimensional structure.
doi:10.1107/S1600536814017140
PMCID: PMC4186144  PMID: 25309277
crystal structure; Schiff base; naphthalene; pyrazolone; pyrrole
4.  Methyl 2,6-diphenyl-1-p-tolyl-4-(p-tolyl­amino)-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate 
In the title compound, C33H32N2O2, the tetra­hydro­pyridine ring adopts a boat conformation with the carbonyl group in an s-cis conformation with respect to the C=C bond of the six-membered tetra­hydro­pyridine ring. The mol­ecular conformation is stabilized by intra­molecular N—H⋯O, C—H⋯O and C—H⋯π inter­actions. Formation of centrosymmetric head-to-head dimers is observed through pairwise inter­molecular N—H⋯O hydrogen bonds. Additional weak C—H⋯O and C—H⋯π inter­actions stabilize the three-dimensional mol­ecular assembly.
doi:10.1107/S1600536812030309
PMCID: PMC3414317  PMID: 22904850
5.  Tetra-μ-acetato-κ8 O:O′-bis­{[4-methyl-2-(m-tolyl­amino)pyridine-κN]copper(II)} 
In the crystal structure of the title binuclear complex, [Cu2(CH3COO)4(C13H14N2)2], the four acetate groups each bridge a pair of CuII atoms. The coordination of the metal atoms is distorted square-pyramidal, with the bonding O atoms comprising a square basal plane and the coordinating N atom of the N-heterocycle occupying the apical position. In the two N-hetercycle ligands, the benzene rings are twisted with respect to the pyridine rings, making dihedral angles of 53.1 (2) and 54.2 (2)°. Intra­molecular N—H⋯O hydrogen bonding is present between the imino and carb­oxy groups. The crystal studied was a non-merohedral twin with a minor twin component of 21.4%.
doi:10.1107/S1600536809055858
PMCID: PMC2979871  PMID: 21579640
6.  3-(p-Tol­yl)-4-{3-[(phenyl­amino)­meth­yl]-7H-[1,2,4]triazolo[3,4-b][1,3,4]thia­diazin-6-yl}sydnone 
In the title compound, C20H17N7O2S (systematic name: 3-(4-methyl­phen­yl)-4-{3-[(phenyl­amino)­meth­yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazin-6-yl}-1,2,3-oxadiazol-3-ium-5-olate), the 3,6-dihydro-2H-1,3,4-thia­diazine ring adopts a half-boat conformation. The oxadiazol-3-ium ring makes dihedral angles of 57.99 (6) and 54.48 (6)° with the phenyl and benzene rings, respectively, while the 1,2,4-triazole ring forms corresponding angles of 37.35 (6) and 73.89 (6)°. The dihedral angle between the oxadiazol-3-ium and 1,2,4-triazole rings is 21.12 (6)°. In the crystal, the mol­ecules are linked via inter­molecular N—H⋯O and C—H⋯N hydrogen bonds into a layer parallel to the (100) plane. The crystal structure is further consolidated by C—H⋯π inter­actions. An intra­molecular C—H⋯O hydrogen bond is also observed, which generates an S(6) ring motif.
doi:10.1107/S1600536811010786
PMCID: PMC3099773  PMID: 21754026
7.  3-(2-Hydroxy­ethyl)-2-(p-tolyl­amino)­quinazolin-4(3H)-one 
In the title compound, C17H17N3O2, the quinazolinone ring system is essentially planar. The benzene ring is twisted with respect to it by a dihedral angle of 32.7 (5)°. The mol­ecular conformation is stabilized by an N—H⋯O hydrogen bond, and the crystal structure is stabilized by inter­molecular O—H⋯N inter­actions.
doi:10.1107/S1600536808040440
PMCID: PMC2967952  PMID: 21581677
8.  (E)-3,5-Dimethyl-1-p-tolyl-4-(p-tolyl­diazen­yl)-1H-pyrazole 
There are two independent mol­ecules, A and B, in the asymmetric unit of the title compound, C19H20N4, in each of which the N=N double bond has an E conformation. The dihedral angles between the pyrazole ring and the p-tolyl rings in the 1- and 4-positions are 22.54 (8) and 35.73 (7)°, respectively, in mol­ecule A. The corresponding dihedral angles in mol­ecule B are 28.13 (8) and 22.18 (8)°. In the crystal, the A and B mol­ecules are linked by weak C—H⋯π inter­actions, leading to inversion dimers in each case.
doi:10.1107/S1600536812000360
PMCID: PMC3275036  PMID: 22346981
9.  Ethyl 1-(2-hy­droxy­eth­yl)-2-p-tolyl-1H-benzimidazole-5-carboxyl­ate 
The asymmetric unit of the title compound, C19H20N2O3, contains two mol­ecules (A and B) with slightly different orientations of the ethyl groups with respect to the attached carboxyl­ate groups. Intra­molecular C—H⋯O hydrogen bonds generate S(8) ring motifs in both mol­ecules A and B. In each mol­ecule, the benzimidazole ring system is essentially planar, with maximum deviations of 0.023 (1) and 0.020 (1) Å, respectively, for mol­ecules A and B. The dihedral angle between the benzimidazole ring system and the phenyl ring is 37.34 (5)° for mol­ecule A and 42.42 (5)° for mol­ecule B. In the crystal, O—H⋯N and C—H⋯O hydrogen bonds link the mol­ecules into [100] columns with a cross-section of two-mol­ecule by two-mol­ecule wide, and further stabilization is provided by weak C—H⋯π and π–π inter­actions [centroid separations = 3.5207 (7) and 3.6314 (8) Å].
doi:10.1107/S1600536810020799
PMCID: PMC3006903  PMID: 21587829
10.  N-(2,4-Dinitro­phen­yl)-N′-(1-p-tolyl­ethyl­idene)hydrazine 
In the title mol­ecule, C15H14N4O4, the dihedral angle between the two benzene rings is 2.21 (7)°. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. The mean planes of the ortho- and para-nitro groups make dihedral angles of 2.17 (17) and 2.05 (16)°, respectively, with the benzene ring to which they are attached. In the crystal structure, weak inter­molecular C—H⋯O hydrogen bonds generate R 2 2(7), R 2 2(13) and R 2 1(10) ring motifs, linking symmetry-related mol­ecules into extended chains along the b axis. In addition, there are inter­molecular C⋯C [3.332 (2)–3.343 (2) Å] contacts which are shorter than the sum of the van der Waals radii. The crystal structure is further stabilized by inter­molecular C—H⋯π and π–π stacking inter­actions [centroid–centroid distance = 3.8090 (9) Å].
doi:10.1107/S1600536809009957
PMCID: PMC2969085  PMID: 21582553
11.  (E)-4-{[(3-Propyl-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-4-yl)imino]­meth­yl}-3-(p-tol­yl)-1,2,3-oxadiazol-3-ium-5-olate 
The title compound, C15H16N6O2S, exists in a trans configuration with respect to the acyclic N=C bond. The 1,2,3-oxadiazol-3-ium ring makes dihedral angles of 10.59 (8) and 73.94 (8)°, respectively, with the 1,2,4-triazole and benzene rings. The mol­ecular structure is stabilized by an intra­molecular C—H⋯S hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked into inversion dimers by pairs of inter­molecular N—H⋯S hydrogen bonds, generating eight-membered R 2 2(8) ring motifs. The dimers are further connected by C—H⋯O hydrogen bonds, forming a sheet parallel to the bc plane. The ethyl group is disordered over two sets of sites with occupancies of 0.744 (7) and 0.256 (7).
doi:10.1107/S1600536811037287
PMCID: PMC3201362  PMID: 22065521
12.  Ethyl 3-[2-(p-tolyl­carbamothio­yl)hydrazinyl­idene]butano­ate 
The title compound, C14H19N3O2S, was obtained from a condensation reaction of N-(p-tol­yl)hydrazinecarbothio­amide and ethyl acetoacetate. The mol­ecule assumes an E configuration; the thio­semicarbazide and ester groups are located on the opposite sides of the C=N bond. The almost planar thio­semicarbazide unit (r.m.s. deviation = 0.0130 Å) is tilted at a dihedral angle of 49.54 (12)° with respect to the benzene ring. Inter­molecular N—H⋯N and N—H⋯S hydrogen bonding stabilizes the crystal structure. The eth­oxy group of the ester unit is disordered over two positions, with a site-occupancy ratio of 0.680 (10):0.320 (10).
doi:10.1107/S160053681004290X
PMCID: PMC3009117  PMID: 21589138
13.  6-[3-(p-Tolyl­sulfonyl­amino)­prop­yl]diquino­thia­zine1  
In the title mol­ecule {systematic name: N-[3-(diquino[3,2-b;2′,3′-e][1,4]thia­zin-6-yl)prop­yl]-4-methyl­benzene­sulfon­amide}, C28H24N4O2S2, the penta­cyclic system is relatively planar [maximum deviation from the mean plane = 0.242 (1) Å]. The dihedral angle between two quinoline ring systems is 8.23 (2)° and that between the two halves of the 1,4-thia­zine ring is 5.68 (3)°. The conformation adopted by the 3-(p-tolyl­sulfonyl­amino)­propyl substituent allows for the formation of an intra­molecular N—H⋯N hydrogen bond and places the benzene ring of this substituent above one of the quinoline fragments of the penta­cyclic system. In the crystal, mol­ecules are arranged via π–π stacking inter­actions into (0-11) layers [centroid–centroid distances = 3.981 (1)–4.320 (1) Å for the rings in the penta­cyclic system and 3.645 (1) Å for the tolyl benzene rings]. In addition, mol­ecules are involved in weak C—H⋯O, which connect the layers, and C—H⋯S hydrogen bonds. The title compound shows promising anti­cancer activity against renal cancer cell line UO-31.
doi:10.1107/S1600536813013950
PMCID: PMC3685109  PMID: 23795128
14.  5-p-Tolyl-1H-tetra­zole 
The title compound, C8H8N4, possesses crystallographic mirror symmetry, with four C atoms lying on the reflecting plane, which bis­ects the phenyl and tetra­zole rings. It is composed of a planar r.m.s. deviation (0.0012 Å) tetra­zole ring which is nearly coplanar with the benzene ring, the dihedral angle being 2.67 (9)°. In the crystal, symmetry-related mol­ecules are linked by inter­molecular N—H⋯N hydrogen bonds. The mol­ecules stack along [100] with a π⋯π inter­action involving the phenyl and tetra­zole rings of adjacent mol­ecules [centroid–centroid distance = 3.5639 (15) Å]. The H atom of the N—H group is disordered over two sites of equal occupancy. The methyl H atoms were modelled as disordered over two sets of sites of equal occupancy rotated by 60° with respect to each other.
doi:10.1107/S1600536809036411
PMCID: PMC2970279  PMID: 21577918
15.  4-{3-[(2-Isopropyl-5-methyl­phen­oxy)meth­yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazin-6-yl}-3-(p-tol­yl)sydnone 
In the title triazolothia­diazin compound, C24H24N6O3S (systematic name: 4-{3-[(2-isopropyl-5-methyl­phen­oxy)meth­yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazin-6-yl}-3-(4-methyl­phen­yl)-1,2,3-oxadiazol-3-ium-5-olate), an intra­molecular C—H⋯O hydrogen bond generates an S(6) ring motif. The two terminal methyl groups of the isopropyl unit are disordered over two sets of positions in a 0.715 (4):0.285 (4) ratio. The mean planes formed through the major and minor disordered isopropyl units are inclined at inter­planar angles of 73.1 (4) and 86.6 (8)°, respectively, with the attached phenyl ring. The 3,6-dihydro-1,3,4-thia­diazine ring adopts a twist-boat conformation. The inter­planar angle formed between 1,2,3-oxadiazole and 1,2,4-triazole rings is 18.80 (11)°. In the crystal, neighbouring mol­ecules are linked into sheets lying parallel to the bc plane by C—H⋯N hydrogen bonds. Weak inter­molecular π–π inter­actions [centroid–centroid distances = 3.2935 (11) and 3.5590 (12) Å] further stabilize the crystal structure.
doi:10.1107/S1600536810030205
PMCID: PMC3007969  PMID: 21588573
16.  1-(3-Chloro­phen­yl)-3-(1-p-tolyl­imidazolidin-2-yl­idene)urea 
In the crystal structure of the title compound, C17H17ClN4O, the existence of only one 2-imino–oxo of the five possible N-amino–imino/O-keto–hydr­oxy tautomers is observed and the dihedral angle between the aromatic rings is 29.78 (11)°. The mol­ecular conformation is stabilized by intra­molecular C—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds, in each case generating a six-membered ring. In the crystal structure, the glide-plane-related mol­ecules are linked into C(4) amide chains by inter­molecular N—H⋯O hydrogen bonds, and an inter­molecular C—H⋯O link also occurs.
doi:10.1107/S1600536808040701
PMCID: PMC2967957  PMID: 21581683
17.  1-(5-Nitro-2-oxoindolin-3-yl­idene)-4-o-tolyl­thio­semicarbazide methanol monosolvate 
In the title compound, C16H13N5O3S·CH4O, the dihedral angle between the isatin unit and the 2-methyl­phenyl group is 41.81 (2)° and intra­molecular N—H⋯O and N—H⋯N hydrogen bonds occur, generating S(6) and S(5) rings, respectively. In the crystal, polymeric chains arise as a result of N—H⋯O, O—H⋯S and C—H⋯O inter­actions.
doi:10.1107/S1600536809043633
PMCID: PMC2971320  PMID: 21578445
18.  N-Hydr­oxy-N-o-tolyl­acetamide 
In the mol­ecule of the title compound, C9H11NO2, the methyl C atom bonded to the ring and the N atom lie in the benzene ring plane. An intra­molecular O—H⋯O hydrogen bond results in the formation of a five-membered planar ring, which is oriented at a dihedral angle of 81.37 (3)° with respect to the benzene ring. In the crystal structure, inter­molecular O—H⋯O hydrogen bonds link the mol­ecules stacked along the b axis. There are also π–π inter­actions between benzene rings with a face-to-face stacking distance of 3.434 Å.
doi:10.1107/S1600536808002468
PMCID: PMC2960255  PMID: 21201552
19.  4-[3-(Phen­oxy­meth­yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazin-6-yl]-3-(p-tol­yl)sydnone 
In the title triazolothia­diazine derivative, C20H16N6O3S {systematic name: 3-(4-methyl­phen­yl)-4-[3-(phen­oxy­meth­yl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thia­diazin-6-yl]-1,2,3-oxadiazol-3-ium-5-olate}, an S(6) ring motif is generated by an intra­molecular C—H⋯O hydrogen bond. The 3,6-dihydro-1,3,4-thia­diazine ring adopts a twist-boat conformation. The dihedral angle between the 1,2,3-oxadiazole and 1,2,4-triazole rings is 46.45 (14)°. The 1,2,3-oxadiazole ring is inclined at dihedral angle of 59.49 (13)° with respect to the benzene ring attached to it. In the crystal structure, inter­molecular C—H⋯O and C—H⋯N hydrogen bonds link neighbouring mol­ecules into two-mol­ecule-thick arrays parallel to the bc plane. A short S⋯O inter­action [2.9565 (19) Å] also occurs.
doi:10.1107/S1600536810029910
PMCID: PMC3007409  PMID: 21588457
20.  Methyl 1-phenyl-3-p-tolyl-1,9b-di­hydro-3H-chromeno[4,3-c]isoxazole-3a(4H)-carboxyl­ate 
In the title compound, C25H23NO4, the pyran ring of the chroman moiety has an envelope conformation with the methyl­ene C atom as the flap. The isoxazole ring has a twist conformation on the O—C bond. The dihedral angle between their mean planes is 57.87 (9)°. The attached phenyl and benzene rings are twisted away from its mean plane by 56.19 (10) and 50.57 (10)°, respectively. These two rings are normal to each other, subtending a dihedral angle of 89.2 (1)°. In the crystal, there are no classical hydrogen bonds; the mol­ecules are linked via C—H⋯π inter­actions, forming a two-dimensional network lying parallel to (10-1).
doi:10.1107/S1600536814002438
PMCID: PMC3998385  PMID: 24764992
21.  (Z)-3-p-Tolyl-2-(p-tolyl­imino)-1,3-thia­zolidin-4-one 
In the title compound, C17H16N2OS, the central thia­zolidin-4-one ring forms dihedral angles of 66.49 (9) and 79.45 (6)° with the two methyl-substituted benzene rings. In the crystal, mol­ecules are stacked in columns along the b axis through C—H⋯π inter­actions. The H atoms of one of the methyl groups are disordered over two orientations with equal site occupancies.
doi:10.1107/S160053681201149X
PMCID: PMC3344088  PMID: 22606091
22.  4-Chloro-N-o-tolyl­benzamide 
In the mol­ecule of the title compound, C14H12ClNO, the two benzene rings are close to coplanar [dihedral angle = 7.85 (4)°]. The amide N—C=O plane makes dihedral angles of 34.04 (4) and 39.90 (3)°, respectively, with the 4-chloro- and 2-methyl­phenyl rings. In the crystal structure, inter­molecular N—H⋯O hydrogen bonds link the mol­ecules into chains.
doi:10.1107/S1600536808030912
PMCID: PMC2959280  PMID: 21201235
23.  2-(4-tert-Butyl­phen­yl)-5-p-tolyl-1,3,4-oxadiazole 
In the title compound, C19H20N2O, the dihedral angles between the 1,3,4-oxadiazole ring and the pendant 4-tert-butyl­phenyl and 4-methyl­phenyl rings are 12.53 (17) and 2.14 (17)°, respectively. In the crystal, mol­ecules are linked by C—H⋯N hydrogen bonds, forming chains.
doi:10.1107/S1600536809051198
PMCID: PMC2980193  PMID: 21580186
24.  1-[4-(Di­methyl­amino)­benzyl­idene]-4-o-tolyl­thio­semicarbazide 
The asymmetric unit of the title compound, C17H20N4S, contains two independent mol­ecules, the main difference between them being the dihedral angles between the benzene rings [19.99 (17) and 9.72 (17)°]. The mol­ecules both have a trans conformation about the C=N double bond and intra­molecular C—H⋯S and N—H⋯N hydrogen bonds are observed in both mol­ecules. In the crystal, mol­ecules are linked by weak N—H⋯S hydrogen bonds with graph-set motif R 2 2(8). In each mol­ecule, all but one of the N atoms and both the S atoms are involved in hydrogen bonding.
doi:10.1107/S1600536813012890
PMCID: PMC3685061  PMID: 23795080
25.  O-Phenyl (cyclo­hexyl­amido)(p-tolyl­amido)­phosphinate 
In the title mol­ecule, C19H25N2O2P, the P atom is bonded in a distorted tetra­hedral environment. The dihedral angle between the two phenyl rings is 89.09 (8)°. The methyl H atoms are disordered over two sets of sites with equal occupancy. The O atom of the P=O group acts as a double hydrogen-bond acceptor of the type (N—H)2⋯(O=)P—, forming R 2 2(8) rings which are further linked into chains along [010].
doi:10.1107/S1600536811018502
PMCID: PMC3120379  PMID: 21754869

Results 1-25 (630541)