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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.  (Z)-3-Methyl-4-[1-(4-methyl­anilino)propyl­idene]-1-phenyl-1H-pyrazol-5(4H)-one 
In the title mol­ecule, C20H21N3O, the central pyrazole ring forms dihedral angles of 4.75 (9) and 49.11 (9)°, respectively, with the phenyl and methyl-substituted benzene rings. The dihedral angle between the phenyl and benzene rings is 51.76 (8)°. The amino group and carbonyl O atom are involved in an intra­molecular N—H⋯O hydrogen bond. In the crystal, π–π inter­actions are observed between benzene rings [centroid–centroid seperation = 3.892 (2) Å] and pyrazole rings [centroid–centroid seperation = 3.626 (2) Å], forming chains along [111]. The H atoms of the methyl group on the p-tolyl substituent were refined as disordered over two sets of sites in a 0.60 (4):0.40 (4) ratio.
doi:10.1107/S1600536813019144
PMCID: PMC3793766  PMID: 24109353
5.  4-{[(E)-(3,5-Dimethyl-1-phenyl-1H-pyrazol-4-yl)methyl­idene]amino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one 
The title Schiff base compound, C23H23N5O, was synthesized by the reaction of 4-amino­phenazone and 3,5-dimethyl-1-phenyl­pyrazole-4-carbaxaldehyde. The mol­ecule adopts an E configuration about the central C=N double bond. A weak intra­molecular C—H⋯O hydrogen bond generates an S(6) ring motif. The dihedral angle between the pyrazole rings is 24.72 (10)° and the dihedral angles between the pyrazole rings and the adjacent phenyl rings are 58.67 (10) and 46.58 (11)°. The crystal structure is stabilized by weak C—H⋯π inter­actions involving the pyrazolone and phenyl rings.
doi:10.1107/S1600536810021173
PMCID: PMC3006732  PMID: 21587838
6.  (E)-4-Methyl-N′-[(4-oxo-4H-chromen-3-yl)methyl­idene]benzohydrazide 
In the title chromone-tethered benzohydrazide derivative, C18H14N2O3, the 4H-chromen-4-one and the –CH=N–NH–CO– units are each essentially planar, with the largest deviations from thei planes being 0.052 (2) and 0.003 (2) Å, respectively. The dihedral angles between the 4H-chromen-4-one and the –CH=N–NH–CO– units, the 4H-chromen-4-one unit and the benzene ring of the 4-tolyl group, and the benzene ring of the 4-tolyl group and the –CH=N–NH–CO– unit are 8.09 (7), 9.94 (5) and 17.97 (8)°, respectively. In the crystal, the mol­ecules form two types of centrosymmetric dimers: one by N—H⋯O hydrogen bonds and the other by π–π stacking inter­actions between the 4H-chromen-4-one unit and the 4-tolyl group [centroid–centroid distance = 3.641 (5) Å]. These dimers form one-dimensional assemblies extending along the a-axis direction. Additional π–π stacking inter­actions between two 4H-chromen-4-one units [centroid–centroid distance = 3.591 (5) Å] and two 4-tolyl groups [centroid–centroid distance = 3.792 (5) Å] organize the mol­ecules into a three-dimensional network.
doi:10.1107/S1600536814008113
PMCID: PMC4011241  PMID: 24860370
7.  Crystal structure of (4Z)-1-(3,4-di­chloro­phen­yl)-4-[hy­droxy(4-methyl­phen­yl)methyl­idene]-3-methyl-4,5-di­hydro-1H-pyrazol-5-one 
The title compound, C18H14Cl2N2O2, crystallizes with two mol­ecules, A and B, in the asymmetric unit. In mol­ecule A, the dihedral angles between the central pyrazole ring and pendant di­chloro­benzene and p-tolyl rings are 2.18 (16) and 46.78 (16)°, respectively. In mol­ecule B, the equivalent angles are 27.45 (16) and 40.45 (18)°, respectively. Each mol­ecule features an intra­molecular O—H⋯O hydrogen bond, which closes an S(6) ring and mol­ecule A also features a C—H⋯O inter­action. In the crystal, weak C—H⋯π interactions and aromatic π–π stacking [shortest centroid–centroid separation = 3.707 (2) Å] generate a three-dimensional network.
doi:10.1107/S160053681402114X
PMCID: PMC4257223  PMID: 25484715
crystal structure; Schiff-base pyrazole derivative; hydrogen bonding; C—H⋯π inter­actions; aromatic π–π stacking
8.  3-Methyl-4-{[(3-{[(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl­idene)(phen­yl)meth­yl]amino­meth­yl}benz­yl)amino](phen­yl)methyl­idene}-1-phenyl-1H-pyrazol-5(4H)-one 
The complete mol­ecule of the title compound, C42H36N6O2, is generated by a crystallographic twofold axis with two C atoms of the central phenyl group lying on the axis. In the independent part of the mol­ecule, one amino group is involved in an intra­molecular N—H⋯O hydrogen bond, and the two adjacent phenyl rings are twisted from the plane of the pyrazolone ring with dihedral angles of 6.82 (3) and 88.32 (6)°. The crystal packing exhibits no classical inter­molecular contacts.
doi:10.1107/S1600536811027000
PMCID: PMC3213468  PMID: 22091047
9.  (E)-[({[(3-Methyl­phen­yl)meth­yl]sulfan­yl}methane­thio­yl)amino](1-phenyl­pentyl­idene)amine 
In the structure of the title compound, C20H24N2S2, the central CN2S2 atoms are planar (r.m.s. deviation = 0.0205 Å) but both benzene rings are twisted out of this plane forming dihedral angles of 23.03 (6) and 84.75 (4)° (tol­yl); the n-butyl group occupies a position normal to the plane [N—C—C—C torsion angle = −84.33 (16)°]. The conformation of the imine bond [1.2888 (18) Å] is E. The syn arrangement of the thione S and amino H atoms enables the formation of N—H⋯S hydrogen bonds between centrosymmetrically related mol­ecules. These lead to eight-membered {⋯HNC=S}2 synthons which are further stabilized by proximate C—H⋯S interactions. The resulting dimeric aggregates are connected into a supra­molecular chain along the c axis by C—H⋯π(tol­yl) inter­actions.
doi:10.1107/S1600536811016965
PMCID: PMC3120291  PMID: 21754762
10.  (Z)-4-[(Ethyl­amino)(furan-2-yl)methyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one 
In the crystal of the title compound, C17H17N3O2, the mol­ecules exist in the keto–enamine form. The pyrazole ring is oriented at 10.59 (4) and 57.98 (5)° to the phenyl and furyl rings, respectively, and the dihedral angle between phenyl and furyl rings is 73.30 (11)°. An intra­molecular N—H⋯O hydrogen bond occurs between imino and carbonyl groups. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into supra­molecular chains along the b axis.
doi:10.1107/S1600536812013712
PMCID: PMC3344430  PMID: 22590192
11.  4-{[(E)-(4-Chloro­phen­yl)methyl­idene]amino}-3-{2-[4-(2-methyl­prop­yl)phen­yl]eth­yl}-1H-1,2,4-triazole-5(4H)-thione 
The asymmetric unit of the title compound, C21H23ClN4S, contains nine crystallographically independent mol­ecules, labelled A to I. The orientation of the 2-[4-(2-methyl­prop­yl)phen­yl]ethyl unit with respect to the rest of the mol­ecule is significantly different in mol­ecules E, F, H and I compared to the other independent mol­ecules. The isobutyl group of mol­ecule B is disordered over two orientations, with occupancies of 0.764 (7) and 0.236 (7). The benzene rings of the chloro­phenyl and methyl­propyl­phenyl units form dihedral angles of 21.90 (11) and 71.47 (11)°, respectively, with the triazole ring in mol­ecule A [9.15 (11) and 80.37 (11)° in B, 7.14 (11) and 84.06 (11)° in C, 25.76 (11) and 76.59 (11)° in D, 13.68 (11) and 76.82 (10)° in E, 8.38 (11) and 69.77 (10)° in F, 30.34 (11) and 78.12 (11)° in G, 21.20 (11) and 71.58 (10)° in H, and 27.65 (11) and 65.23 (11)° in I]. In each independent mol­ecule, a C—H⋯S hydrogen bond is observed. The crystal packing is stabilized by N—H⋯S and C—H⋯S hydrogen bonds, and by C—H⋯π inter­actions involving the methyl­propyl­phenyl ring.
doi:10.1107/S160053680901650X
PMCID: PMC2969595  PMID: 21583109
12.  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
13.  (Z)-4-[(3-Aminona­phthalen-2-yl­amino)(phen­yl)methyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one 
The mol­ecule of the title compound, C27H22N4O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 12.73 (11), 65.17 (6) and 49.82 (6)°, respectively, with the two benzene rings and the naphthalene ring system. In the crystal, pairs of mol­ecules are linked by inter­molecular N—H⋯N hydrogen bonds, forming dimers. The secondary amino group is involved in an intra­molecular N—H⋯O hydrogen bond.
doi:10.1107/S1600536812034770
PMCID: PMC3435809  PMID: 22969655
14.  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
15.  Benzyl 3-[(E)-(furan-2-yl)methyl­idene]-2-methyldithio­carbazate 
In the title compound, C14H14N2OS2, the furan ring exhibits rotational disorder over two orientations, with an occupancy ratio of 0.508 (7):0.492 (7). The furan and phenyl rings form dihedral angles of 8.2 (6) (major occupancy component), 14.8 (6) (minor occupancy component) and 73.65 (9)°, respectively, with the central residue (C4N2S2), indicating a twisted conformation for the mol­ecule. The methyl group and the thione S atom are syn and the conformation about the imine bond is E. In the crystal, C—H⋯π inter­actions involving the phenyl ring are observed.
doi:10.1107/S1600536812035520
PMCID: PMC3435764  PMID: 22969635
16.  (2E)-2-{[3-Methyl-5-(2-naphth­yloxy)-1-phenyl-1H-pyrazol-4-yl]methyl­idene}hydrazinecarbothio­amide monohydrate 
In the title compound, C22H19N5OS·H2O, the naphthalene ring system and the benzene ring [dihedral angle = 85.19 (8)°] make dihedral angles of 87.02 (9) and 14.41 (10)°, respectively, with the pyrazole ring. The mean plane through the 2-methyl­enehydrazinecarbothio­amide group [C—N—N—C(=S)—N; maximum deviation = 0.022 (1) Å] is slightly twisted from the pyrazole ring [dihedral angle = 5.60 (11)°]. In the crystal, mol­ecules are linked by N—H⋯S, N—H⋯O, O—H⋯S, O—H⋯N and C—H⋯S hydrogen bonds into sheets parallel to the ab plane. π–π inter­actions are also observed [centroid-to-centroid distances = 3.7778 (12) and 3.7010 (12) Å].
doi:10.1107/S1600536812039815
PMCID: PMC3470403  PMID: 23125816
17.  (Z)-4-[(2-Amino-4,5-dichloro­anilino)(phenyl)methyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one 
The mol­ecule of the title compound, C23H18Cl2N4O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 32.61 (19), 76.73 (14) and 52.57 (19)° with the three benzene rings. The secondary amino group is involved in an intra­molecular N—H⋯O hydrogen bond. In the crystal, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds, forming inversion dimers. An offset stacking inter­action is observed between the chloro-substituted benzene rings protruding on both sides of these dimers [centroid–centroid distance = 3.862 (1) Å].
doi:10.1107/S160053681204086X
PMCID: PMC3515247  PMID: 23284467
18.  N′-[Bis(benzyl­sulfan­yl)methyl­idene]-4-meth­oxy­benzohydrazide 
In the title compound, C23H22N2O2S2, the dihedral angles between the 4-meth­oxy-substituted phenyl ring and the other two phenyl rings are 84.4 (4) and 77.7 (1)°, respectively, while the dihedral angle between the two phenyl rings is 57.5 (2)°. The amino group is not involved in an N—H hydrogen bond. The crystal packing is established by inter­molecular C—H⋯O packing inter­actions involving a relatively rare weak three-center hydrogen bond between the keto O atom and H atoms of the two nearby phenyl rings, which link the mol­ecules into chains running along the a axis. Additional weak inter­molecular hydrogen-bond inter­actions between the 4-meth­oxy O atom and one of the phenyl rings and provide added stability to the crystal packing.
doi:10.1107/S1600536810025389
PMCID: PMC3007250  PMID: 21588233
19.  (Z)-4-[(2-Amino­anilino)(phen­yl)methyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one 
The mol­ecule of the title compound, C23H20N4O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 10.33 (11), 65.34 (11) and 63.52 (10)° with the three benzene rings. In the crystal, the mol­ecules are linked by inter­molecular N—H⋯N hydrogen bonds, generating chains parallel to the b axis. The secondary amino group is involved in an intra­molecular N—H⋯O hydrogen bond.
doi:10.1107/S1600536811037470
PMCID: PMC3201420  PMID: 22065632
20.  3-Hydr­oxy-N′-[(Z)-(5-methyl-2-fur­yl)methyl­idene]naphthalene-2-carbo­hydrazide 
The asymmetric unit of title compound, C17H14N2O3, contains three independent mol­ecules. In one of these mol­ecules, the 5-methyl-2-furyl group is disordered over two sets of sites with an occupancy ratio of 0.747 (3):0.253 (3). In the two ordered mol­ecules, the furan and naphthalene rings are oriented at dihedral angles of 11.05 (12) and 32.2 (5)°. In the disordered mol­ecule, the furan rings with major and minor occupancies are oriented at dihedral angles of 41.4 (2) and 26.6 (13)°, respectively, with the corresponding naphthalene ring. An intra­molecular O—H⋯O hydrogen bond occurs within each mol­ecule. In the crystal, mol­ecules are linked by N—H⋯O, N—H⋯(N,O) and C—H⋯O inter­actions.
doi:10.1107/S1600536809043141
PMCID: PMC2971404  PMID: 21578435
21.  Crystal structure of (Z)-3-benz­yloxy-6-[(2-hy­droxy­anilino)methyl­idene]cyclo­hexa-2,4-dien-1-one 
In the title compound, C20H17NO3, the methyl­idene­cyclo­hexa-2,4-dienone moiety is approximately planar [maximum deviation = 0.0615 (10) Å] and is oriented at diherdral angles of 69.60 (7) and 1.69 (9)° to the phenyl and hy­droxy­benzene rings, respectively. The amino group links with the carbonyl O atom via an intra­molecular N—H⋯O hydrogen bond, forming an S(6) ring motif. In the crystal, the mol­ecules are linked by O—H⋯O hydrogen bonds and weak C—H⋯O and C—H⋯π inter­actions, forming a three-dimensional supra­molecular architecture.
doi:10.1107/S1600536814024568
PMCID: PMC4257387  PMID: 25553053
crystal structure; pharmaceutical applications; industrial applications; azomethines; hydro­philicity; drug properties; hydrogen bonding; C—H⋯π inter­actions
22.  3-[Hy­droxy(3-meth­oxy­phen­yl)methyl­idene]-2-(2-oxo-2-phenyl­eth­yl)-3,4-dihydro-2H-1λ6,2-benzothia­zine-1,1,4-trione 
In the title mol­ecule, C24H19NO6S, the heterocyclic thia­zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.180 (5) and 0.497 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The benzene rings of the benzothia­zine unit and the meth­oxy­phenyl group are almost coplanar, with the dihedral angle between the mean planes of these rings being 5.9 (2)°, while the benzene ring of the 2-oxo-2-phenyl­ethyl group is inclined at 79.68 (11) and 81.01 (10)°, respectively, to these rings. The mol­ecular structure is consolidated by intra­molecular O—H⋯O and C—H⋯N inter­actions, and the crystal packing is stabilized by weak C—H⋯O hydrogen bonds.
doi:10.1107/S1600536812009002
PMCID: PMC3343951  PMID: 22590032
23.  Crystal structure of (E)-N-{[3-methyl-1-phenyl-5-(1H-pyrrol-1-yl)-1H-pyrazol-4-yl]methyl­idene}hydroxyl­amine 
The title compound, C15H14N4O, crystallizes with two mol­ecules in the asymmetric unit with similar conformations (r.m.s. overlay fit for the 20 non-H atoms = 0.175 Å). In the first mol­ecule, the dihedral angles between the planes of the central pyrazole ring and the pendant phenyl and pyrrole rings are 42.69 (8) and 51.88 (6)°, respectively, with corresponding angles of 54.49 (7) and 49.61 (9)°, respectively, in the second mol­ecule. In the crystal, the two mol­ecules, together with their inversion-symmetry counterparts, are linked into tetra­mers by O—H⋯N hydrogen bonds. The tetra­mers form layers parallel to (211) through pairwise C—H⋯π inter­actions.
doi:10.1107/S1600536814023514
PMCID: PMC4257281  PMID: 25484837
crystal structure; pyrrole ring; hydrogen bonding; hydroxyl­amine
24.  (E)-2-Methyl-6-[(1-phenyl-1H-pyrazol-4-yl)methyl­idene]cyclo­hexa­none 
The asymmetric unit of the title compound, C17H18N2O, contains two independent mol­ecules. In both, the cyclo­hexane ring adopts a flattened chair conformation, and the 3- and 4-methyl­ene C atoms as well as the methyl C atoms are disordered over two positions, the occupancy of the major component being 68 (1)% in one mol­ecule and 64 (1)% in the other. The phenyl and pyrazole rings in both mol­ecules are approximately coplanar, the r.m.s. deviations being 0.048 and 0.015 Å, respectively. Weak inter­molecular C—H⋯O hydrogen bonding is present in the crystal structure.
doi:10.1107/S160053681102126X
PMCID: PMC3151926  PMID: 21837019
25.  (2E)-2-[(3-Methyl-5-phen­oxy-1-phenyl-1H-pyrazol-4-yl)methyl­idene]hydrazinecarbothio­amide 
In the title compound, C18H17N5OS, the mean plane of the pyrazole ring [maximum deviation = 0.0031 (12) Å] forms dihedral angles of 19.6 (4) and 9.3 (5)° with the two disorder components of the N-bound benzene ring (with equal occupancies for the two orientations) and a dihedral angle of 72.58 (8)° with the C—O-bonded benzene ring. The mol­ecule exists in a trans conformation with respect to the N=C bond [1.2792 (19) Å]. The mol­ecular structure features an intra­molecular C—H⋯O hydrogen bond, forming an S(6) ring. In the crystal, N—H⋯N and N—H⋯S hydrogen bonds result in the formation of zigzag layers lying parallel to (10-1).
doi:10.1107/S1600536812026931
PMCID: PMC3393955  PMID: 22798820

Results 1-25 (630556)