Naphthyl Ring System Research Articles

Synthesis, non-spherical structure refinement and Hirshfeld surface analysis of racemic 2,2'-diisobut-oxy-1,1'-bi-naphthalene.

In the racemic title compound, C28H30O2, the naphthyl ring systems subtend a dihedral angle of 68.59 (1)° and the mol-ecular conformation is consolidated by a pair of intra-molecular C-H⋯π contacts. The crystal packing features a weak C-H⋯π contact and van der Waals forces. A Hirshfeld surface analysis of the crystal structure reveals that the most significant contributions are from H⋯H (73.2%) and C⋯H/H⋯C (21.2%) contacts.

Crystal structure of nafamostat dimesylate.

Nafamostat dimesylate {systematic name: [amino({6-[(4-{[amino(iminiumyl)methyl]amino}phenyl)carbonyloxy]naphthalen-2-yl})methylidene]azanium bis(methanesulfonate)}, C19H19N5O2 2+·2CH3O3S-, is a broad-spectrum serine protease inhibitor and has been applied clinically as an anti-coagulant agent during hemodialysis and for treatment of severe acute pancreatitis (SAP). Since nafamostat contains flexible moieties, it is necessary to determine the conformation to understand the structure-activity relationships. The divalent cation has a screw-like motif. The guanidinium group is approximately perpendicular to the naphthyl ring system, subtending a dihedral angle of 84.30 (14)°. In the crystal, the nafamostat mol-ecules form columnar structures surrounded by a hydro-philic region.

3-(2-Meth-oxy-phen-yl)-2,3-di-hydro-1H-benzo[f]chromen-1-one.

In the title compound, C20H16O3, the 2-meth-oxy-phenyl ring is tilted by 50.67 (3)° with respect to the naphthyl ring system. The central pyran ring has an envelope conformation with the C atom bearing the pendant ring system as the flap. The meth-oxy group attached to the benzene ring is slightly twisted [C-C-O-C = -15.2 (1)°] from the ring. In the crystal, weak C-H⋯O inter-actions link the mol-ecules into C(7) chains propagating along [101].

3-(4-Iodo-phen-yl)-2,3-di-hydro-1H-benzo[f]chromen-1-one.

In the title compound, C19H13IO2, the dihedral angle between the naphthyl ring system and the pendant iodo-phenyl ring is 72.48 (11)°. In the crystal, C-H⋯π inter-actions and I⋯O [3.293 (2) Å] halogen bonds are observed, which combine to generate a herringbone packing motif.

Crystal structure of benzyl 2-naphthyl ether, a sensitiser for thermal paper.

The title compound [systematic name: 2-(benz-yloxy)naphthalene], C17H14O, which is used as a sensitiser for thermal paper, has a twisted conformation with a dihedral angle of 48.71 (12)° between the phenyl ring and the naphthyl ring system. In the crystal, one mol-ecule inter-acts with six neighbouring mol-ecules via inter-molecular C-H⋯π inter-actions to form a herringbone mol-ecular arrangement.

Ethyl (naphthalen-2-yloxy)acetate

In the title compound, C14H14O3, the dihedral angle between the naphthyl ring system and the side chain is 9.00 (14)°, and the ethoxy chain adopts an extended conformation [C—O—C—C = 176.0 (3)°]. There are no directional interactions in the crystal beyond normal van der Waals contacts.

(1R,2R)-8-Bromo-1-[(E)-2-(4-bromophenyl)ethenyl]-2-nitro-1,2-dihydronaphtho[2,1-b]furan

The title compound,C20H13Br2NO3, contains the dihydrobenzofuran moiety, which is present in the physiologically active components of many medicinal plants. The naphthyl ring system is nearly perpendicular to the phenyl ring, while the mean plane of the double bond is almost coplanar with the phenyl ring [dihedral angles of 79.14 (3) and 13.56 (1)°, respectively]. The nitro group and bromobenzene alkenyl group aretransto one another on opposite sides of the furan ring. There are two stereogenic centres, and each has theRconfiguration. In the crystal, there are very weak intermolecular C—H...Br interactions.

Crystal structure of 2,2'-bis-[(2-chloro-benz-yl)-oxy]-1,1'-bi-naphthalene.

In the title binaphthyl compound, C34H24Cl2O2, the dihedral angle between the two naphthyl ring systems (r.m.s. deviations = 0.016 and 0.035 Å) is 76.33 (8)°. The chloro­phenyl rings make dihedral angles of 58.15 (12) and 76.21 (13)° with the naphthyl ring to which they are linked. The dihedral angle between the planes of the two chloro­phenyl rings is 27.66 (16)°. In the crystal, C—H⋯O hydrogen bonds link mol­ecules into chains propagating along [1-10]. The chains are linked by C—H⋯π inter­actions, forming a three-dimensional framework.

Crystal structure of N-[(naphthalen-1-yl)carbamo-thio-yl]cyclo-hexa-necarboxamide.

The title compound, C18H20N2OS, displays whole-mol­ecule disorder over two adjacent sets of sites with an occupancy ratio of 0.630 (11):0.370 (11). In each disorder component, the cyclo­hexyl ring shows a chair conformation with the exocyclic C—C bond in an equatorial orientation. The dihedral angles between the cyclo­hexyl ring (all atoms) and the naphthyl ring system are 36.9 (6) for the major component and 20.7 (12)° for the minor component. Each component features an intra­molecular N—H⋯O hydrogen bond, which closes an S(5) ring. In the crystal, inversion dimers linked by pairs of N—H⋯S hydrogen bonds generate R 2 2(8) loops for both components. Aromatic π–π stacking inter­actions [shortest centroid–centroid separation = 3.593 (9) Å] and a C—H⋯π inter­action are also observed.

Crystal structure of (R)-2'-benz-yloxy-[1,1'-binaphthalen]-2-yl tri-fluoro-methane-sulfonate.

In the title compound, C28H19F3O4S, a new 2′-benz­yloxy (R)-BINOL derivative containing a tri­fluoro­methane­sulfonate group in the 2-position, the planes of the two naphthyl ring systems (r.m.s. deviations = 0.012 and 0.019 Å) are at an angle of 73.36 (2)°, and the planes of the benzyl ring and the naphthyl ring system bound to the ether O atom are at an angle of 75.67 (4)°. In the crystal, mol­ecules are linked via C—H⋯F hydrogen bonds, forming chains propagating along [100]. The chains are linked via a weak C—F⋯π inter­action and weak π–π inter­actions [shortest inter-centroid distance = 3.9158 (12) Å], forming a three-dimensional structure. The absolute structure of the mol­ecule in the crystal was determined by resonant scattering [Flack parameter = 0.02 (6)].

Crystal structure of bis[1-(naphthalen-1-ylmethyl)pyridinium] bis(2,2-dicyanoethene-1,1-dithiolato-κ2S,S′)nickelate(II)

A new ion-pair complex, (C16H14N)2[Ni(C4N2S2)2] or (1-NaMePy)2[Ni(imnt)2], where 1-NaMePy is 1-(4-naphthyl-methyl-ene)pyridinium and imnt is 2,2-di-cyano-ethene-1,1-di-thiol-ate, was obtained by the direct reaction of NiCl2, K2imnt and (1-NaMePy)(+)Br(-) in H2O. The asymmetric unit contains a [1-NaMePy](+) cation and one half of an Ni(imnt)2 (2-) anion. The Ni(II) ion lies on an inversion centre and adopts a square-planar configuration with Ni-S bond lengths of 2.200 (1) and 2.216 (1) Å. In the [1-NaMePy](+) cation, the naphthyl ringsystem and the pyridinium ring make a dihedral angle of 90.0 (2)°. In the crystal, C-H⋯N and C-H⋯Ni hydrogen bonds, as well as π-π inter-actions between the chelate ring and the pyridinium ring [centroid-centroid distance = 3.675 (2) Å] link the ions into a three-dimensional network.

Methyl 1-ethyl-3'-[hy-droxy(naphthalen-1-yl)meth-yl]-1'-methyl-2-oxo-spiro-[indo-line-3,2'-pyrrolidine]-3'-carboxyl-ate.

In the title compound, C27H28N2O4, the pyrrolidine ring adopts a twist conformation. The plane of the indole ring is almost perpendicular to that of the pyrrolidine ring, making a dihedral angle of 88.50 (6)°. The planes of the naphthyl ring system and the pyrrolidine ring are tilted by an angle of 55.86 (5)°. The mol­ecular conformation is stabilized by intra­molecular O—H⋯O and O—H⋯N hydrogen bonds.

Dicyclohexylbis(naphthalen-1-ylmethyl)phosphonium chloride chloroform disolvate

In the title solvated phosphonium salt, C34H40P+·Cl−·2CHCl3, the two cyclo­hexyl and two 1-naphthyl­methyl groups at the P atom are in a distorted tetra­hedral arrangement [105.26 (6)–113.35 (6)°]. Both cyclo­hexyl rings adopt a chair conformation. The dihedral angle between the naphthyl ring systems is 74.08 (3)°.

2-[(E)-(Naphthalen-2-yl)iminomethyl]phenol

In the title compound, C17H13NO, the azomethine double bond adopts an E conformation. The naphthyl ring system and the benzene ring form a dihedral angle of 8.09 (10)°. The near-planar conformation of the molecule is consolidated by an intra­molecular O—H⋯N hydrogen bond, which forms an S(6) ring. In the crystal, mol­ecules are arranged in a zigzag fashion parallel to the c axis.

2-Fluoro-N'-[(2-hydroxynaphthalen-1-yl)methylidene]benzohydrazide.

In the title mol­ecule, C18H13FN2O2, the hy­droxy group is involved in an intra­molecular O—H⋯N hydrogen bond. The naphthyl ring system and the benzene ring form a dihedral angle of 31.0 (2)°. In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into chains propagating in [101].

1,1′-Binaphthyl-2,2′-diyl benzylphosphoramidate

In the title compound, C27H20NO3P, the P atom exhibits a somewhat distorted PNO3 tetra­hedral geometry, with the O—P—O angle for the binaphthyl fragment being 102.82 (6)°. The dihedral angle between the naphthyl ring systems is 59.00 (2)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R 2 2(8) loops.

1-[(Ferrocen-1-yl)meth-yl]-3-(naphthalen-1-yl)thio-urea.

In the title compound, [Fe(C5H5)(C17H15N2S)], the cyclo­penta­dienyl (Cp) rings are almost parallel and essentially eclipsed, with a dihedral angle between the Cp ring planes of 0.807 (11)°. The Fe atom is slightly closer to the substituted cyclo­penta­dienyl ring, with an Fe–centroid distance of 1.6510 (8) Å, compared with 1.6597 (8) Å for the unsubstituted ring. The bridging unit between the substituted Cp ring and the naphthyl ring system is planar within 0.0174 Å and makes dihedral angles of 59.032 (10) and 66.02 (2)°, respectively, with these two rings. The angle between the substituted Cp ring and the naphthyl ring system is 72.094 (18)°. The H atoms of the NH groups of the thio­urea moiety are positioned anti with respect to each other. In the crystal, mol­ecules form centrosymmetric dimers via pairs of N—H⋯S hydrogen bonds.

N′-[(2-Hydroxynaphthalen-1-yl)methylidene]-4-nitrobenzohydrazide

In the title mol­ecule, C18H13N3O4, the hy­droxy group is involved in the formation of an intra­molecular O—H⋯N hydrogen bond. The dihedral angle between the planes of the benzene ring and the naphthyl ring system is 9.0 (2)°. In the crystal, mol­ecules are linked through N—H⋯O hydrogen bonds into chains along the c axis.

N-(1-Naphthyl)benzenesulfonamide

In the title compound, C16H13NO2S, the C—SO2—NH—C torsion angle is −70.1 (2)°. The dihedral angle between the planes of the naphthyl ring system and the phenyl ring is 34.67 (4)°. In the crystal, mol­ecules are linked by inter­molecular N—H⋯O hydrogen bonds into chains along [100]. There are also π–π inter­actions between adjacent naphthyl groups [inter­planar spacing = 3.541 (3) Å] for mol­ecules stacked along [100].

7-Phenyl-7H-dinaphtho[2,1-b:1′,2′-d]phosphole 7-oxide

In the title compound, C26H17OP, the naphthyl ring systems are bent away from each other [dihedral angle = 30.81 (8)°]. In the crystal, weak inter­molecular C—H⋯O inter­actions link the mol­ecules into helical chains along the 21 screw axis.