Naphthalene Ring System Research Articles

1-[(2-Hydroxyphenyl)(pyrrolidin-1-yl)methyl]naphthalen-2-olN,N-dimethylformamide monosolvate

The title compound, C21H21NO2·C3H7NO, was synthesized by solvent-free one-pot three-component reaction of naphthalen-2-ol, 2-hy­droxy­benzaldehyde and pyrrolidine. The dihedral angle between the naphthalene ring system and the benzene ring is 77.74 (6)°. The pyrrolidine ring assumes an envelope conformation. An intra­molecular O—H⋯N and an inter­molecular O—H⋯O hydrogen bond are observed.

(3E,5E)-3,5-Bis(naphthalen-1-yl-methyl-idene)piperidin-4-one.

In the title compound, C27H21NO, the piperidine ring adopts a chair conformation. The mean plane through the piperidine ring makes dihedral angles of 49.27 (5) and 63.07 (5)° with the naphthalene ring systems. In the crystal, mol­ecules are linked into dimers via pairs of inter­molecular C—H⋯O inter­actions, generating ten-membered R 2 2(10) ring motifs. C—H⋯π inter­actions further stabilize the crystal structure.

1,1′-(Phenylmethylene)dinaphthalen-2-ol

In the title compound, C27H20O2, the phenyl ring is oriented with respect to the naphthalene ring systems at 57.87 (6) and 85.12 (6)°. The two naphthalene ring systems make a dihedral angle of 70.10 (4)°. In the mol­ecule, the hy­droxy groups are involved in a strong intra­molecular O—H⋯O hydrogen bond. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds occur. A weak C—H⋯π inter­action is also observed in the crystal.

1-[(4-Bromophenyl)(morpholin-4-yl)methyl]naphthalen-2-ol

The title compound, C21H20BrNO2, was obtained from a condensation reaction of 4-bromo­benzaldehyde, 2-naphthol and morpholine. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond, closing a six-membered ring. The dihedral angle between the naphthalene ring system and the benzene ring is 76.72 (8)°. In addition to the intra­molecular hydrogen bond, the O—H groups of centrosymmetrically related mol­ecules form short inter­molecular H⋯O contacts of 2.59 Å. These mol­ecules are also linked by pairs of C—H⋯O inter­actions, generating an R 2 2(14) motif.

(E)-4-{2-[(2-Hy-droxy-naphthalen-1-yl)methyl-idene]hydrazinecarbon-yl}pyridinium nitrate.

The title compound, C17H14N3O2 +·NO3 −, is an aroylhydrazone-based material consisting of a 4-(hydrazinecarbon­yl)pyridinium cation and a nitrate anion. In the cation, the dihedral angle between the benzene ring and the naphthalene ring system is 2.20 (7)°. In the cation, the configuration about the C=N bond is E. There is an intra­molecular O—H⋯N hydrogen bond in the cation, and the supra­molecular structure is stabilized by inter­molecular N—H⋯O hydrogen bonds and weak C—H⋯O contacts between the cation and the nitrate anion.

Crystal Structure and Solution Structural Dynamic Feature of 1,8-Dibenzoyl-2,7-Dimethoxynaphthalene

The crystal structure and the dynamic feature of molecular structure in solution for 1,8-dibenzoyl-2,7-dimethoxynaph-thalene are revealed by X-ray crystallographic analysis and VT-NMR measurements. In crystal, the molecule of the title compound is located on a twofold rotation axis. The two benzoyl groups are situated in an opposite direction. The dihedral angle between the mean planes of the phenyl ring and the naphthalene ring system is 80.25(6). The benzene ring and carbonyl moiety in each benzoyl group are almost coplanar. The molecular packing is stabilized by weak C–H…O hydrogen bonds and aπ-πstacking interaction between the benzene rings [centroid-centroid and interplanar distances of 3.6383(10) and 3.294 , respectively]. In solution, the temperature-dependent rotation behavior of the C–C bond between the benzene ring and the ketonic carbonyl group has been observed by1H VT-NMR measurements. Furthermore, comparison of the C–C bond rotation behavior between the benzene ring and the carbonyl group with 1-ben-zoyl-2,7-dimethoxynaphthalene has clarified that the C–C bond between the ketonic carbonyl group and the naphthalene ring rotates slower than the 1,8-dibenzoylated homologue.

N,N′-Bis(2,6-diethylphenyl)acenaphthylene-1,2-diimine

The title compound, C32H32N2, has crystallographic twofold rotation symmetry, with two C atoms lying on the rotation axis. The dihedral angle between the substituted benzene ring and the naphthalene ring system is 79.8 (1)°. The crystal structure is stabilized by C—H⋯N inter­actions, which form a chain motif along the b-axis direction.

2,2′-[2,4-Bis(naphthalen-1-yl)cyclobutane-1,3-diyl]bis(1-methylpyridinium) diiodide: thermal-induced [2 + 2] cycloaddition reaction of a heterostilbene

The asymmetric unit of the title compound, C36H32N2 2+·2I−, consists of one half-mol­ecule of the cation and one I− anion. The cation is located on an inversion centre. The dihedral angle between the pyridinium ring and the naphthalene ring system in the asymmetric unit is 19.01 (14)°. In the crystal, the cations and the anions are linked by C—H⋯I inter­actions into a layer parallel to the bc plane. Intra- and inter­molecular π–π inter­actions with centroid–centroid distances of 3.533 (2)–3.807 (2) Å are also observed.

2,7-Dimethoxy-8-(2,4,6-trimethylbenzoyl)naphthalen-1-yl](2,4,6-trimethylphenyl)methanone

In the title compound, C32H32O4, the dihedral angle between the two benzene rings of the 2,4,6-trimethyl­benzoyl groups is 71.43 (7)°. The dihedral angles between the two benzene rings and the naphthalene ring system are 81.58 (5) and 84.92 (6)°. An intra­molecular C—H⋯O inter­action is observed.

4-[(2-Hydroxynaphthalen-1-yl)(morpholin-4-yl)methyl]benzonitrile

The title compound, C22H20N2O2, was synthesized via a multicomponent reaction using naphthalen-2-ol, morpholine and 4-formyl­benzonitrile. The dihedral angle between the naphthalene ring system and the benzene ring is 81.25 (10)°. The morpholine ring adopts a chair conformation. The mol­ecular conformation is stabilized by intra­molecular O—H⋯N and C—H⋯O hydrogen bonds. In the crystal, inter­molecular C—H⋯N hydrogen bonds link mol­ecules into helical chains running parallel to the c axis.

2,2′-(1,1′-Binaphthyl-2,2′-diyldiimino)diethanol-κ3N,N′,O]dichloridocopper(II)

In the title complex, [CuCl2(C24H24N2O2)], the CuII cation is N,N′,O-chelated by a 2,2′-(1,1′-binaphthyl-2,2′-diyldiimino)­diethanol ligand and coordinated by two chloride anions in a distorted square-pyramidal geometry. In the diethanol ligand, the two naphthalene ring systems are twisted with respect to each other at a dihedral angle of 68.30 (9)°. The uncoord­inated hy­droxy group links with a coordinated chloride anion via an intra­molecular O—H⋯Cl hydrogen bond. Inter­molecular N—H⋯O and N—H⋯Cl hydrogen bonds occur in the crystal structure.

8-(4-Butoxybenzoyl)-2,7-dimethoxynaphthalen-1-yl](4-butoxyphenyl)methanone

The mol­ecule of the title compound, C34H36O6, is located on a twofold rotation axis. The two 4-but­oxy­benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti­parallel. The dihedral angles between the benzene rings and the naphthalene ring system are 71.70 (4)°. In the crystal, the mol­ecules are connected via C—H⋯π inter­actions into a layer parallel to (010).

5,5′-Bis(naphthalen-2-yl)-2,2′-bi(1,3,4-oxadiazole)

The title mol­ecule, C24H14N4O2, lies on an inversion centre and the asymmetric unit containg one half-mol­ecule. The naphthalene ring systems are twisted slightly with respect to the oxadiazole rings, making a dihedral angle of 1.36 (6)°. These mol­ecules are π-stacked along the crystallographic a axis, with an inter­planar distance of 3.337 (1) Å. Adjacent mol­ecules are slipped from the ‘ideal’ cofacial π-stack in both the long and short mol­ecular axis (the long mol­ecular axis is defined as the line through the naphthalene C atom in the 6-position and the mol­ecular center, the short mol­ecular axis is in the mol­ecular plane perpendicular to it). The slip distance along the long mol­ecular axis (S 1) is 7.064 (1) Å, nearly a two-ring-length displacement. The side slip (S 2, along the short mol­ecular axis) is 1.159 (8) Å.

(E)-1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)-3-(6-meth-oxy-naphthalen-2-yl)prop-2-en-1-one.

In the title compound, C33H24F2O3, the central benzene ring makes dihedral angles of 44.71 (10), 47.80 (10) and 63.68 (9)° with the two fluoro-substituted benzene rings and the naphthalene ring system, respectively. In the crystal, mol­ecules are connected via inter­molecular C—H⋯F and C—H⋯O hydrogen bonds. Furthermore, the crystal structure is stabilized by weak C—H⋯π and π–π inter­actions [centroid–centroid distance = 3.6816 (13) Å].

1,3-Bis(propan-2-yl)naphthalene

In the title compound, C16H20, one of the isopropyl groups shows almost equal displacements [1.252 (1) and −1.270 (1) Å] of its methyl-C atoms from the mean plane of the naphthalene ring system, while the other shows asymmetric displacements [1.586 (2) and −0.315 (1) Å]. In the crystal, the mol­ecules are linked into sheets lying in the ab plane by three C—H⋯π contacts, two involving donors belonging to the isopropyl groups and the third a donor atom from the naphthalene ring system. The different orientations of the isopropyl groups might be attributed to the fact that the C—H⋯π inter­action involving one of them is enhanced by the C—H⋯π inter­action involving the aromatic ring.

Rac-1,2,3,4-Tetrahydro-1,4-methanoanthracene-6,7-dicarbonitrile

The title compound, C17H12N2, comprises a norbornane unit having a dicyanona­phthalene ring fused on one side. Both cyano groups are twisted slightly out of the plane of the naphthalene ring system [C—C—C—C torsion angle = 1.9 (2)°]. In the crystal, inversion-related mol­ecules are linked by pairs of weak C—H⋯N hydrogen bonds, forming dimers.

N-(Naphthalen-1-yl)benzamide

In the title compound, C17H13NO, the N—H and C=O bonds are anti with respect to each other. The dihedral angle between the naphthalene ring system and the phenyl ring is 86.63 (5)°. In the crystal, N—H⋯O hydrogen bonds link mol­ecules into chains along [010].

(3,6-Dimethoxynaphthalen-2-yl)(2,4,6-trimethylphenyl)methanone

In the title compound, C22H22O3, the dihedral angle between the naphthalene ring system and the benzene ring is 79.95 (5)°. The bridging carbonyl C—C(=O)—C group makes dihedral angles of 24.21 (7) and 82.43 (8)°, respectively, with the naphthalene ring system and the benzene ring. In the crystal, weak inter­molecular C—H⋯O inter­actions link mol­ecules into chains parallel to the c axis.

N-(3,5-Dichloro-phen-yl)-2-(naphthalen-1-yl)acetamide.

In the title compound, C18H13Cl2NO, the naphthalene ring system [maximum deviation = 0.038 (4) Å] and the benzene ring form dihedral angles of 69.5 (2) and 37.2 (2)°, respectively, with the essentially planar acetamide unit [maximum deviation = 0.004 (4) Å]. The naphthalene ring system forms a dihedral angle of 52.36 (18)° with the benzene ring. In the crystal, mol­ecules are linked via inter­molecular N—H⋯O hydrogen bonds, forming chains along [001].

N-(4-Bromo-phen-yl)-2-(naphthalen-1-yl)acetamide.

In the title compound, C18H14BrNO, the naphthalene ring system and the benzene ring form dihedral angles of 78.8 (2) and 19.7 (2)°, respectively, with the acetamide C—C(=O)—N plane. The naphthalene ring system forms a dihedral angle of 64.88 (19)° with the benzene ring. In the crystal, mol­ecules are linked via inter­molecular bifurcated (N,C)—H⋯O hydrogen bonds, generating an R 2 1(6) ring motif, forming chains along the b axis.