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1.  1-{(Z)-[3-(1-Hy­droxy­eth­yl)anilino]methyl­idene}naphthalen-2(1H)-one 
In the title compound, C19H17NO2, the dihedral angle between the benzene ring and the naphthalene ring system is 9.72 (5)°, while the torsion angle of the C—N—C—C bridging group is 179.24 (17)°. The methyl group of the 1-phenyl­ethanol moiety is disordered over two positions with a refined occupancy ratio of 0.775 (5):0.225 (5). The mol­ecular conformation is stabil­ized by an intra­molecular N—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, forming zigzag chains propagating along the c-axis direction. Neighbouring chains are linked via C—H⋯O inter­actions, forming a two-dimensional slab-like network parallel to the bc plane.
doi:10.1107/S1600536812050635
PMCID: PMC3588315  PMID: 23476368
2.  (2Z)-1-(5-Hy­droxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-(4-meth­oxy­anilino)but-2-en-1-one 
The central residue in the title compound, C21H21N3O3, is close to planar (r.m.s. deviation = 0.0753 Å for all non-H atoms from OH to NH inclusive): the hy­droxy, amino and carbonyl groups all lie to the same side of the mol­ecule (the conformation about the ethene bond is Z), facilitating the formation of intra­molecular O—H⋯O and N—H⋯O hydrogen bonds that close S(6) rings. However, overall the mol­ecule is twisted as the terminal aromatic rings are not coplanar with the central plane [dihedral angles = 20.55 (5) and 80.90 (4)° for the N-bound phenyl ring and the meth­oxy­benzene ring, respectively]. The dihedral angle between the rings is 82.14 (7)°. Supra­molecular layers in the ac plane mediated by C—H⋯π inter­actions are found in the crystal.
doi:10.1107/S1600536811032491
PMCID: PMC3200693  PMID: 22064834
3.  Crystal structure of (Z)-4-[1-(4-acetyl­anilino)ethyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one 
In the solid state, the title compound, adopts the keto–amine tautomeric form, with the H atom attached to the N atom, which participates in an intra­molecular N—H⋯O hydrogen bond with an S(6) ring motif. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds to generate C(16) chains propagating in the [301] direction.
In the solid state, the title compound, C20H19N3O2, adopts the keto–amine tautomeric form, with the H atom attached to the N atom, which participates in an intra­molecular N—H⋯O hydrogen bond with an S(6) ring motif. The dihedral angles between the pyrazole ring and the phenyl and benzene rings are 3.69 (10) and 46.47 (9)°, respectively. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds, generating C(16) chains propagating in [301]. Weak aromatic π–π stacking inter­actions [centroid–centroid distances = 3.6123 (10) and 3.6665 (10) Å] link the chains into a three-dimensional network.
doi:10.1107/S2056989014026899
PMCID: PMC4331847
crystal structure; Schiff bases; pyrazolone derivatives; keto–amine tautomeric form; hydrogen bonding; π–π stacking inter­actions
4.  (E)-2-(2,3-Dimethyl­anilino)-N′-(thio­phen-2-yl­methyl­idene)benzohydrazide 
In the title compound, C20H19N3OS, the central benzene ring makes dihedral angles of 45.36 (9) and 55.33 (9)° with the thio­phene ring and the dimethyl-substituted benzene ring, respectively. The dihedral angle between the thio­phene ring and dimethyl-substituted benzene ring is 83.60 (9)°. The thio­phene ring and the benzene ring are twisted from the mean plane of the C(=O)—N—N=C bridge [maximum deviation = 0.0860 (13) Å], with dihedral angles of 23.86 (9) and 24.77 (8)°, respectively. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds to the same acceptor atom, forming sheets lying parallel to the bc plane. The crystal packing also features C—H⋯π inter­actions.
doi:10.1107/S160053681203259X
PMCID: PMC3414973  PMID: 22904960
5.  N-(4-Meth­oxy­phen­yl)-6-methyl-2-phenyl-5-{[4-(tri­fluoro­meth­yl)anilino]meth­yl}pyrimidin-4-amine 
The title compound, C26H23F3N4O, crystallizes with two symmetry-independent mol­ecules in the asymmetric unit, denoted A and B, which differ mainly in the rotation of the meth­oxy­phenyl ring. The –CF3 group of mol­ecule B is disordered by rotation, with the F atoms split over two sets of sites; the occupancy factor for the major component is 0.853 (4). The dihedral angles between the pyrimidine ring and the attached phenyl, meth­oxy­phenyl and tri­fluoro­methyl­phenyl rings are 8.1 (2), 37.5 (2) and 70.7 (2)°, respectively, in mol­ecule A, and 9.3 (2), 5.3 (2) and 79.7 (2)° in mol­ecule B. An intra­molecular N—H⋯N hydrogen bond occurs in each mol­ecule. In the crystal, two crystallographically independent mol­ecules associate into a dimer via a pair of N—H⋯N hydrogen bonds, with a resulting R 2 2(12) ring motif and π–π stacking inter­actions [centroid–centroid distance = 3.517 (4) Å] between the pyrimidine rings. For the A mol­ecules, there are inter­molecular C—H⋯O hydrogen bonds between an aryl C atom of meth­oxy­phenyl ring and a meth­oxy O atom of an adjacent mol­ecule. A similar inter­action is lacking in the B mol­ecules.
doi:10.1107/S160053681303170X
PMCID: PMC3885078  PMID: 24454254
6.  2-(2,3-Dimethyl­anilino)benzohydrazide 
In the title compound, C15H17N3O, the dihedral angle between the benzene rings is 58.05 (9)°. The non-H atoms of the hydrazide group lie in a common plane (r.m.s. deviation = 0.0006 Å) and are close to coplanar with their attached benzene ring [dihedral angle = 8.02 (9)°]. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif in the mol­ecule, and a short intra­molecular contact (H⋯H = 1.88 Å) is also observed. In the crystal, mol­ecules are linked by pairs of N—H⋯N hydrogen bonds into inversion dimers. The crystal packing also features C—H⋯π inter­actions.
doi:10.1107/S1600536812032576
PMCID: PMC3414975  PMID: 22904962
7.  A series of N-(2-phenyl­ethyl)nitro­aniline derivatives as precursors for slow and sustained nitric oxide release agents 
A series of N-(2-phenyl­ethyl)nitro­aniline derivatives is presented, demonstrating that modest changes in the functional groups cause significant differences in mol­ecular conformation, inter­molecular inter­actions and packing.
2,4-Di­nitro-N-(2-phenyl­ethyl)aniline, C14H13N3O4, (I), crystallizes with one independent mol­ecule in the asymmetric unit. The adjacent amine and nitro groups form an intra­molecular N—H⋯O hydrogen bond. The anti conformation about the ethyl C—C bond leads to the phenyl and aniline rings being essentially parallel. Mol­ecules are linked into dimers by inter­molecular N—H⋯O hydrogen bonds, such that each amine H atom participates in a three-centre inter­action with two nitro O atoms. Though the dimers pack so that the arene rings of adjacent mol­ecules are parallel, the rings are staggered and π–π inter­actions do not appear to be favoured. 4,6-Di­nitro-N,N′-bis­(2-phenyl­ethyl)benzene-1,3-di­amine, C22H22N4O4, (II), differs from (I) in the presence of a second 2-phenyl­ethyl­amine group on the substituted ring. Compound (II) also crystallizes with one unique mol­ecule in the asymmetric unit. Both amine groups are involved in intra­molecular N—H⋯O hydrogen bonds with adjacent nitro groups. Although one ethyl group adopts an anti conformation as in (I), the other is gauche, with the result that the pendant phenyl rings are not parallel. The amine group that is part of the gauche conformation participates in a three-centre N—H⋯O hydrogen bond with the nitro group of a neighbouring mol­ecule, leading to dimers as in (I). The other amine H atom does not form any inter­molecular hydrogen bonds. The packing leads to separations of ca 3.4 Å of the parallel anti phenyl and amino­benzene rings. 2-Cyano-4-nitro-N-(2-phenyl­ethyl)aniline, C15H13N3O2, (III), differs from (I) only in having a cyano group in place of the 2-nitro group. The absence of the adjacent nitro group eliminates the intra­molecular N—H⋯O hydrogen bond. Mol­ecules of (III) adopt the same anti conformation about the ethyl group as in (I), but crystallize in the higher-symmetry monoclinic space group P21/n. The mol­ecules are linked into dimers via N—H⋯N amine–cyano hydrogen bonds, while the nitro groups are not involved in any N—H⋯O inter­actions. Owing to the different symmetry, the mol­ecules pack in a herringbone pattern with fewer face-to-face inter­actions between the rings. The closest such inter­actions are about 3.5 Å between rings that are largely slipped past one another. 4-Methyl­sulfonyl-2-nitro-N-(2-phenyl­ethyl)aniline, C15H16N2O4S, (IV), differs from (I) in having a methyl­sulfonyl group in place of the 4-nitro group. The intra­molecular N—H⋯O hydrogen bond is present as in (I). However, unlike (I), the conformation about the ethyl group is gauche, so the two arene rings are nearly per­pen­dicular rather than parallel. The packing is significantly different from the other three structures in that there are no inter­molecular hydrogen bonds involving the N—H groups. The mol­ecules are arranged in tetra­gonal columns running along the c axis, with the aniline rings mostly parallel and separated by ca 3.7 Å. Taken together, these structures demonstrate that modest changes in functional groups cause significant differences in mol­ecular conformation, inter­molecular inter­actions and packing.
doi:10.1107/S0108270113025869
PMCID: PMC3818095  PMID: 24192194
crystal structure; N-(2-phenyl­ethyl)nitro­aniline derivatives; secondary amines; nitric oxide release agents
8.  4-Anilino-3-nitro-N-phenyl­benzamide 
In the title compound, C19H15N3O3, the anilino and benzamide rings make dihedral angles of 10.66 (16) and 50.39 (16)°, respectively, with the nitro-substituted benzene ring. The nitro group is slightly twisted by 11.49 (17)° with respect to the attached benzene ring. There is an intra­molecular N—H⋯O hydrogen bond forming an S(6) ring. In the crystal, weak inter­molecular N—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules into a chain parallel to the b axis. Futhermore, weak slipped π–π inter­actions [centroid–centroid distance = 3.819 (2) Å, inter­planar distance = 3.567 Å and offset angle [how is the offset angle defined?] = 21°] between the anilino ring and its symmetry-related counterpart may help to stabilize the packing.
doi:10.1107/S1600536810043849
PMCID: PMC3011462  PMID: 21589566
9.  (RS)-(2-Bromo-4-fluoro­anilino)[2-(4,6-dimethoxy­pyrimidin-2-yl­oxy)phen­yl]acetonitrile 
In the title compound, C20H16BrFN4O3, the pyrimidine and 2-bromo-4-fluoro­phenyl rings are twisted away from the central benzene ring, making dihedral angles of 77.7 (1) and 85.5 (1), respectively. A pair of C—H⋯F inter­actions is involved in an R 2 2(8) motif, linking the mol­ecules into dimers. These ring motifs are situated about the crystallographic centres of symmetry. C—H⋯O hydrogen bonds link the dimers into chains running parallel to [11]. Additionally, a weak C—F⋯π-electron ring inter­action was observed in the crystal packing [F⋯Cg = 3.459 (4) Å; Cg is the centroid of the pyrimidine ring]. There is also an intra­molecular N—H⋯Br inter­action in the structure.
doi:10.1107/S1600536809033819
PMCID: PMC2970001  PMID: 21577686
10.  4-Anilino-3-nitro­benzonitrile 
In the title compound, C13H9N3O2, the aromatic rings are twisted with respect to each other, making a dihedral angle of 49.41 (9)°. The nitro group and the nitrile group are nearly in the plane of the benzonitrile ring, the largest deviation from the plane being 0.123 (1) Å. There is an intra­molecular N—H⋯O hydrogen bond forming an S(6) ring. Weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into a chain parallel to the c axis. Futhermore, slipped π–π inter­actions between symmetry-related phenyl rings [centroid–centroid distance 3.808 (1) Å, inter­planar distance 3.544 (8) Å with an offset of 21.5°] stabilize the structure.
doi:10.1107/S1600536810043862
PMCID: PMC3011760  PMID: 21589567
11.  Dimethyl (2Z)-2-[4-((1Z)-1-{2-[(2Z,5Z)-5-(2-meth­oxy-2-oxo­ethyl­idene)-4-oxo-3-phenyl-1,3-thia­zolidin-2-yl­idene]hydra­zin-1-yl­idene}eth­yl)anilino]but-2-ene­dio­ate 
The mol­ecule of the title compound, C26H24N4O7S, adopts a trans conformation about the central N—N bond, presumably to minimize steric between the substituents on these two atoms. An intra­molecular N—H⋯O hydrogen bond occurs. The phenyl ring is disordered over two sets of sites, with an occupancy ratio of 0.624 (8):0.376 (8). The azolidine ring is essentially planar [maximum deviation = 0.008 (5) Å] and makes a dihedral angle of 4.3 (2)° with the benzene ring and dihedral angles of 74.1 (3) and 69.1 (5)°, respectively, with the mean planes of the major and minor components of the disordered phenyl ring. The packing in the crystal is aided by the formation of several weak C—H⋯O and C—H⋯N inter­actions.
doi:10.1107/S1600536813032042
PMCID: PMC3885086  PMID: 24454262
12.  5-[(4-Fluoro­anilino)meth­yl]-6-methyl-N-(4-methyl­phen­yl)-2-phenyl­pyrimidin-4-amine 
In the title compound, C25H23FN4, the pyrimidine ring makes dihedral angles of 11.3 (2), 24.5 (2) and 70.1 (2)° with the phenyl and two benzene rings, and the mol­ecular conformation is stabilized by an intra­molecular N—H⋯N hydrogen bond with an S(6) ring motif. In the crystal, a pair of weak C—H⋯F hydrogen bonds link two mol­ecules into an inversion dimer with an R 2 2(16) motif. In the dimer, there is also an inter­molecular π–π stacking inter­action [centroid–centroid distance = 3.708 (4) Å] between the fluorinated benzene rings. The dimers are further linked by a C—H⋯π inter­action, so forming a column along the c axis.
doi:10.1107/S160053681203783X
PMCID: PMC3470299  PMID: 23125712
13.  5-[(3,5-Dichloro­anilino)meth­yl]-N-(3,5-dichloro­phen­yl)-6-methyl-2-phenyl­pyrimidin-4-amine 
In the title compound, C24H18Cl4N4, the pyrimidine ring makes dihedral angles of 19.1 (2), 4.1 (2) and 67.5 (2)°, respectively, with phenyl and two benzene rings, and the mol­ecular conformation is stabilized by an intra­molecular N—H⋯N hydrogen bond closing a six-membered ring with an S(6) motif. In the crystal, a pair of inter­molecular N—H⋯N hydrogen bonds connect two mol­ecules, forming inversion dimers with R 2 2(12) motifs. C—H⋯π inter­actions links the dimers into a chain running along the a-axis direction. There are also π–π stacking inter­actions [centroid–centroid distance = 3.666 (4) Å] between the benzene rings of adjacent chains.
doi:10.1107/S160053681204665X
PMCID: PMC3588999  PMID: 23476235
14.  [2-(2,3-Dimethyl­anilino)phen­yl]methanol 
In the title compound, C15H17NO, the 2,3-dimethyl­phenyl group is disordered over two sites with an occupancy ratio of 0.869 (3):0.131 (3). The major and minor components of the 2,3-dimethyl­anilino group are planar, with r.m.s. deviations of 0.0214 and 0.0303 Å, respectively, and are oriented at a dihedral angle of 2.6 (6)°. The phenyl­methanol–benzene ring is oriented at dihedral angles of 83.16 (6) and 81.0 (3)° with respect to the major and minor components of the 2,3-dimethyl­anilino group, respectively. An S(6) ring motif is present due to intra­molecular N—H⋯O hydrogen bonding. In the crystal, mol­ecules are connected into supra­molecular chains via O—H⋯O hydrogen bonding along the b axis. C—H⋯π inter­actions help to stabilize the crystal structure.
doi:10.1107/S1600536810033325
PMCID: PMC3008038  PMID: 21588712
15.  2,6-Dichloro­aniline–4-(2,6-dichloro­anilino)­pent-3-en-2-one (1/2) 
The asymmetric unit of the title compound, C6H5Cl2N·2C11H11Cl2NO, is composed of one mol­ecule of an enamino–ketone [i.e. –(2,6-dichloro­phenyl­amino)­pent-3-en-2-one] and half a mol­ecule of 2,6-dichloro­aniline, the whole mol­ecule of the latter component being generated by twofold rotational symmetry. In this latter mol­ecule, there are two intra­molecular N—H⋯Cl contacts. In the enamino–ketone mol­ecule, there is an N—H⋯O hydrogen bond of moderate strength, and the dihedral angle between the benzene ring and penta­none fragment [C—C(—N)=C—C(=O)—C; planar within 0.005 (1) Å] is 81.85 (7)°. In the crystal, two mol­ecules of the enamino–ketone are bridged by a mol­ecule of 2,6-dichloro­aniline via N—H⋯O hydrogen bonds of moderate strength. There are also π–π inter­actions present, involving the benzene rings of inversion-related enamino–ketone mol­ecules [centroid–centroid distance = 3.724 (4) Å].
doi:10.1107/S1600536812049227
PMCID: PMC3588339  PMID: 23476422
16.  (2Z)-3-(4-Chloro­anilino)-1-(5-hy­droxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one 
With the exception of the terminal benzene rings, the atoms in the title compound, C20H18ClN3O2, are approximately coplanar (r.m.s. deviation = 0.0495 Å). The benzene/chloro­benzene rings form dihedral angles of 3.02 (4) and 41.59 (5)°, respectively, with this plane. The hy­droxy, amino and carbonyl groups all lie to the same side of the mol­ecule, enabling the formation of intra­molecular O—H⋯O and N—H⋯O hydrogen bonds that close S(6) rings. The configuration about the 2-butene bond is Z. Supra­molecular chains mediated by C—H⋯Cl inter­actions and aligned along the c axis are found in the crystal packing. These assemble into layers that are connected by weak π–π inter­actions between centrosymmetrically related chloro­benzene rings [3.8156 (9) Å].
doi:10.1107/S1600536811029473
PMCID: PMC3213593  PMID: 22091170
17.  (E,E)-4-{4-[3-(4-Chloro­anilino)-1-hydroxy­but-2-enyl­idene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}­benzene­sulfonamide 
The mol­ecule of the title compound, C20H19ClN4O4S, features a central pyrazole ring that possesses a benzene substituent, as well as a conjugated =C—C=C—Cmeth­yl substituent. The benzene ring is slightly twisted [dihedral angle = 7.7 (2)°] with respect to the five-membered ring; the mean plane of the zigzag =C—C=C—C fragment [torsion angle = 178.0 (4)°] is also slightly twisted [dihedral angle = 10.6 (4)°]. The amine and hy­droxy groups form intra­molecular hydrogen bonds. The amide group uses one of its H atoms to form a hydrogen bond to the sulfamyl O atom of an inversion-related mol­ecule. Adjacent dimers are further linked by an N—Hamido⋯Npyrazole hydrogen bond to generate a linear chain. The crystal studied is a nonmerohedral twin with a minor twin component of 25.6 (2)%.
doi:10.1107/S1600536811020617
PMCID: PMC3151870  PMID: 21836998
18.  Bromido({2-[2-(diphenyl­phosphan­yl)benzyl­idene]hydrazin-1-yl­idene}(4-meth­oxy­anilino)methane­thiol­ato)palladium(II) acetone monosolvate 
In the title compound, [PdBr(C27H23N3OPS)]·C3H6O, the coordination geometry about the PdII atom is distorted square-planar, arising from the attached Br, S, P and N atoms (N and Br are trans), the maximum deviation from the plane being 0.2053 (4) Å for the N atom. The three benzene rings attached to the P atom make dihedral angles of 69.78 (7), 87.05 (7) and 77.50 (7)° with each other. An intra­molecular C—H⋯N hydrogen bond forms an S(6) ring motif. In the crystal, the complex mol­ecules form infinite chains along the a-axis direction through C—H⋯Br inter­actions, and a C—H⋯O inter­action links the main mol­ecule with the acetone solvent mol­ecule.
doi:10.1107/S1600536812028760
PMCID: PMC3393237  PMID: 22807805
19.  3-Methyl-1-phenyl-4-[(Z)-phen­yl(4-acetamido­anilino)methyl­idene]-1H-pyrazol-5(4H)-one 
In the title compound, C25H22N4O2, the dihedral angles between the central pyrazole ring and the phenyl and benzene rings are 37.01 (3), 75.58 (7) and 49.67 (8)°. An intra­molecular N—H⋯O hydrogen bond generates an S(6) motif. In the crystal, N—H⋯O hydrogen bonds link mol­ecules into a zigzag chain extended along the b axis.
doi:10.1107/S1600536812026840
PMCID: PMC3393943  PMID: 22798808
20.  2-Anilino-4-(1,3-benzothia­zol-2-yl)-5-(4-chloro­benzo­yl)thio­phene-3-carbonitrile 
In the title compound, C25H14ClN3OS2, the central thio­phene ring [maximum deviation = 0.011 (1) Å] makes dihedral angles of 55.72 (5), 13.36 (5) and 46.77 (4)° with the adjacent chloro-substituted benzene ring, the benzene ring and the 1,3-benzothia­zole ring system [maximum deviation = 0.012 (1) Å], respectively. An intra­molecular C—H⋯S(thienyl) hydrogen bond generates an S(6) ring motif in the mol­ecule. In the crystal, mol­ecules are linked by pairs of N—H⋯N hydrogen bonds into inversion dimers and the dimers are further connected by C—H⋯O hydrogen bonds into tapes running along [100]. Aromatic π–π stacking inter­actions are also observed [centroid-to-centroid distances = 3.6116 (6) and 3.7081 (6) Å].
doi:10.1107/S1600536812032588
PMCID: PMC3414976  PMID: 22904963
21.  (E)-Ethyl 2-anilino-5-[3-(dimethyl­amino)­acrylo­yl]-4-phenyl­thio­phene-3-carboxyl­ate 
In the title compound, C24H24N2O3S, the phenyl rings form dihedral angles of 55.65 (11) and 79.60 (11)° with the plane of the thio­phene ring. The mol­ecular conformation is stabilized by an intra­molecular N—H⋯O hydrogen bond, generating an S(6) ring motif. In the crystal, centrosymmetrically related mol­ecules are linked into dimers by two pairs of C—H⋯O inter­actions.
doi:10.1107/S1600536813003231
PMCID: PMC3588423  PMID: 23476543
22.  1,3-Bis(2-anilino-2-oxoeth­yl)-1H-imidazol-3-ium chloride acetonitrile monosolvate 
In the title compound, C19H19N4O2 +·Cl−·C2H3N, the dihedral angle between the two phenyl rings is 69.57 (8)° while the dihedral angles between the imidazole ring and the phenyl rings are 70.61 (7) and 82.11 (7)°. In the crystal, N—H⋯Cl, C—H⋯O, C—H⋯Cl and C—H⋯N hydrogen bonds link the imidazolium cations, chloride anions and acetonitrile solvent mol­ecules into a two-dimensional hydrogen-bonded network parallel to (001); an intra­molecular C—H⋯O hydrogen bond is also observed.
doi:10.1107/S1600536811048410
PMCID: PMC3239007  PMID: 22199856
23.  Ethyl 3-amino-5-anilino-4-cyano­thio­phene-2-carboxyl­ate 
In the title compound, C14H13N3O2S, the dihedral angle between the thio­phene and phenyl rings is 24.95 (8)°. The mol­ecular structure is consolidated by intra­molecular N—H⋯O and C—H⋯S inter­actions. The crystal structure features N—H⋯N and N—H⋯O hydrogen bonds forming centrosymmetric R 2 2(12) dimers, which are linked into a two-dimensional network parallel to (011) with an S(6)R 2 2 S(6) motif. In addition, π–π stacking inter­actions [centroid–centroid distance = 3.7013 (12) Å] occur between the thio­phene and phenyl rings of adjacent mol­ecules.
doi:10.1107/S1600536813018734
PMCID: PMC3793747  PMID: 24109334
24.  (Z)-3-[1-(4-Methoxy­anilino)ethyl­idene]-4,5-dihydro­furan-2(3H)-one 
In the title compound, C13H15NO3, the dihydro­furan­one ring is planar to within 0.012 (4) Å and it forms a dihedral angle of 42.8 (2)° with the benzene ring. The amino­ethyl­idene group is coplanar with the dihydro­furan­one ring. The meth­oxy group is slightly twisted away from the benzene ring. An intra­molecular N—H⋯O hydrogen bond, generating an S(6) ring, is observed. In the crystal structure, the mol­ecules exist as C—H⋯O hydrogen-bonded dimers.
doi:10.1107/S1600536808016504
PMCID: PMC2961739  PMID: 21202952
25.  1-[(E)-(2-Phenoxy­anilino)methyl­ene]naphthalen-2(1H)-one 
The mol­ecule of the title compound, C23H17NO2, a Schiff base derived from 2-hydr­oxy-1-naphthaldehyde, crystallizes in the keto–amine tautomeric form. The dihedral angle between the aniline and hydroxy­benzene rings is 77.41 (17)°, whereas the planes of the naphthaldehyde and fused aniline benzene rings are nearly coplanar, making a dihedral angle of 8.29 (15)°. Intra­molecular N—H⋯O hydrogen bonding, a characteristic hydrogen bond for Schiff bases, helps to stabilize the mol­ecular structure. Weak inter­molecular C—H⋯π inter­actions are present in the crystal structure.
doi:10.1107/S1600536810013851
PMCID: PMC2979135  PMID: 21579180

Results 1-25 (300258)