Crystal structure of 1,8-dibenzoyl-2,7-di-phen-oxy-naphthalene.

In the title compound, C36H24O4, the benzene rings of the benzoyl and phen-oxy groups make dihedral angles of 75.01 (4), 75.78 (4), 83.17 (5) and 80.84 (5)° with the naphthalene ring system. In the crystal, two types of C-H⋯π inter-actions between the benzene rings of the benzoyl groups and the naphthalene unit, and two kinds of π-π inter-actions between the benzene rings, with centroid-centroid distances of 3.879 (1) and 3.696 (1) Å, are observed.

Crystal structure of 2,7-dieth-oxy-1,8-bis-(4-nitro-benzo-yl)naphthalene.

The title compound, C28H22N2O8, possesses crystallographically imposed twofold symmetry, with the two central carbon atoms of the naphthalene unit lying on the rotation axis. The two benzoyl groups in the mol-ecule are twisted away from the attached naphthalene unit with a C-C-C=O torsion angle of 49.05 (15)° between the naphthalene unit and the carbonyl group. The dihedral angle between the naphthalene ring system and the benzene ring is 77.17 (5)°. In the crystal, pairs of C-H⋯O=C hydrogen bonds link the mol-ecules into a double-column structure along the c axis. The mol-ecules are further linked by C-H⋯O=N hydrogen bonds, forming a three-dimensional network. C-H⋯π inter-actions between the methyl-ene group and the naphthalene unit and π-π inter-actions between the naphthalene ring systems [centroid-centroid distances of 3.7858 (7)-3.7860 (7) Å] are also observed.

Crystal structure of 1-(2-fluoro-benzo-yl)-2,7-di-meth-oxy-naphthalene.

The asymmetric unit of the compound, C19H15FO3, contains two independent molecules. Each molecule has essentially the same feature of non-coplanarly accumulated aromatic rings whereby the aroyl group at the 1-position of the naphthalene ring system is twisted almost perpendicularly to the ring system [dihedral angles of 86.52 (8) and 89.66 (8)°]. In the crystal structure, mol-ecules of the same conformer are stacked into columns parallel to the a axis by van der Waals inter-actions only.

Head-to-tail square-shaped cyclic hydrogen bonds leading to dimeric aggregates: 1,8-dibenzoyl-2,7-dihydroxynaphthalene and a comparison with its analogous benzoylnaphthalene.

The title compound, C24H16O4, crystallized with two independent molecules in the asymmetric unit. Both carbonyl groups in these molecules form intramolecular O-H...O=C hydrogen bonds with neighbouring hydroxy groups, affording six-membered cyclic structures. In the crystal, dimeric aggregates arise from two intermolecular O-H···O=C hydrogen bonds between both independent molecules, forming head-to-tail square-shaped cyclic ···O···H···O···H··· hydrogen bonds. These dimeric aggregates are connected into layers in the bc plane by intermolecular (naphthalene)C-H...O=C interactions. On the other hand, the analogous compound bearing methoxy groups at the 2- and 7-positions of the naphthalene ring, namely 1,8-dibenzoyl-2,7-dimethoxynaphthalene [Nakaema et al. (2008). Acta Cryst. E64, o807], forms a three-dimensional molecular network via C-H···O=C and π-π interactions between the benzoyl groups. These results show that the intramolecular O-HvO=C hydrogen bonds in the title compound control the orientations of the benzoyl groups and thus promote the formation of the cyclic intermolecular O-H···O=C interactions involving the same donor and acceptor groups in pairs of molecules.

{2,7-Dieth-oxy-8-[(naphthalen-2-yl)carbon-yl]naphthalen-1-yl}(naphthalen-2-yl)methanone.

In the title compound, C36H28O4, the two 2-naphthoyl groups at the 1- and 8-positions of the central 2,7-dieth-oxy-naphthalene ring system are aligned almost anti-parallel and make a dihedral angle of 48.35 (5)°. The dihedral angles between the central 2,7-dieth-oxy-naphthalene ring system and the terminal naphthalene ring systems are 77.64 (4) and 73.73 (4)°. In the crystal, mol-ecules are linked into chains along the a-axis direction by dual C-H⋯O inter-actions between naphthoyl groups.

[2,7-Dihy-droxy-8-(4-phen-oxy-benzo-yl)naphthalen-1-yl](4-phen-oxy-phen-yl)methanone.

In the title compound, C(36)H(24)O(6), the benzoyl groups at the 1- and 8-positions of the naphthalene system are in an anti orientation. Both carbonyl groups form intra-molecular O-H⋯O hydrogen bonds with hy-droxy groups affording six-membered rings. The benzene rings of the benzoyl groups make dihedral angles of 59.26 (13) and 59.09 (13)° with the naphthalene ring system. Zigzag C-H⋯O chains and ladder C-H⋯O chains between the phenoxybenzoyl groups along the ab diagonals form an undulating checkered sheet. The molecules are further connected into a three-dimensional network by C-H⋯π interactions.

1-Benzoyl-naphthalene-2,7-diyl dibenzoate.

In the title compound, C(31)H(20)O(5), the phenyl rings of the benzo-yloxy and benzoyl groups are twisted away from the naphthalene ring system by 64.27 (6), 73.62 (5) and 80.41 (6)°. In the crystal, C-H⋯O hydrogen bonds and C-H⋯π inter-actions link the mol-ecules, forming tubular chains parallel to the b axis. The chains are further connected into a three-dimensional network by C-H⋯π inter-actions and π-π stacking contacts [centroid-centroid distances = 3.622 (10)-3.866 (12) Å].

[8-(4-Phen-oxy-benzo-yl)-2,7-bis-(propan-2-yl-oxy)naphthalen-1-yl](4-phen-oxy-phen-yl)methanone.

The entire title mol-ecule, C(42)H(36)O(6), is completed by the application of a twofold axis. The 4-phen-oxy-benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti-parallel. The dihedral angle between the best planes of the benzene rings of the benzoyl moieties and the naphthalene ring system is 70.52 (5)° and that between the best planes of the benzene rings of the phen-oxy groups and the naphthalene ring system is 27.80 (6)°. In the crystal, mol-ecules are linked into a three-dimensional architecture by C-H⋯O and C-H⋯π inter-actions.

[2,7-Dimeth-oxy-8-(4-meth-oxy-benzo-yl)naphthalen-1-yl](4-meth-oxy-phen-yl)methanone chloro-form monosolvate.

In the title compound, C28H24O6·CHCl3, the two 4-meth-oxy-benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti-parallel, the benzene rings making a dihedral angle of 25.76 (7)°. The naphthalene ring system makes dihedral angles of 72.51 (7) and 73.33 (7)° with the benzene rings. In the crystal, the naphthalene mol-ecules are linked by C-H⋯O inter-actions, forming a helical chain along the b-axis direction. A C-H⋯Cl inter-action is also observed between the aroylated naphthalene and chloro-form mol-ecules. The chloro-form mol-ecule is disordered over two positions with site occupancies of 0.478 (5) and 0.522 (5).

(8-Benzoyl-2,7-dieth-oxy-naphthalen-1-yl)(phen-yl)methanone.

In the title compound, C28H24O4, the benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti-parallel, and the benzene rings make a dihedral angle of 20.03 (7)°. The dihedral angles between the benzene rings and the naphthalene ring system are 68.42 (5) and 71.69 (5)°. In the crystal, adjacent mol-ecules are linked via C-H⋯O hydrogen bonds, forming chains propagating along [100].

(2,7-Dimeth-oxy-naphthalen-1-yl)(4-meth-oxy-phen-yl)methanone.

In the mol-ecule of the title compound, C20H18O4, the dihedral angle between the naphthalene ring system and the benzene ring is 81.74 (5)°. An inter-molecular C-H⋯O inter-action is formed between an H atom at the 6-position of the naphthalene ring and the O atom of the meth-oxy group at the 7-position.

(8-Benzoyl-2,7-dimeth-oxy-naphthalen-1-yl)(4-phen-oxy-phen-yl)methanone.

In the mol-ecule of the title compound, C32H24O5, the benzoyl group and the 4-phenoxy substituted benzoyl group at the 1- and 8-positions of the naphthalene ring system are aligned almost anti-parallel. The two benzene rings make a dihedral angle of 21.18 (10)°, and are inclined to the naphthalene ring system by 86.53 (9) and 82.95 (8)°, respectively. In the crystal, C-H⋯O inter-actions are observed involving aromatic and meth-oxy H atoms with ketonic carbonyl O atoms, as well as C-H⋯π inter-actions between aromatic H atoms and the π-systems of naphthalene and benzene rings. These interactions form a three-dimensional architecture and afford a waved alignment of the naphthalene ring systems along the c axis.

(2,7-Dimeth-oxy-naphthalen-1-yl)(4-phen-oxy-phen-yl)methanone.

In the title mol-ecule, C25H20O4, the naphthalene and phen-oxy groups are oriented nearly perpendicular with respect to the benzene ring of the benzoyl group, with dihedral angles of 89.61 (5) and 86.13 (6)°, respectively. The crystal structure features C-H⋯O and C-H⋯π inter-actions.

{2,7-Dimeth-oxy-8-[4-(propan-2-yl-oxy)benzo-yl]naphthalen-1-yl}[4-(propan-2-yl-oxy)phen-yl]methanone.

The title compound, C32H32O6, crystallized with two independent molecules in the asymmetric unit. Each molecule has essentially the same feature of non-coplanar aromatic rings whereby the two 4-isopropoxybenzoyl groups are twisted in a perpendicular manner to the naphthalene ring and oriented in the same direction (syn-orientation). The benzene rings of the aroyl groups make dihedral angles of 16.13 (7) and 25.31 (7)° in the two molecules. These benzene rings make dihedral angles of 88.38 (8) and 75.32 (7)° with the naphthalene ring system in one molecule, and 89.71 (7) and 82.11 (7)° in the other. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming a three-dimensional network. In one independent molecule, the 2-propyl groups of both isoprop-oxy groups are disordered over two positions with site occupancies of 0.512 (3) and 0.488 (3).

{2,7-Dieth-oxy-8-[(naphthalen-1-yl)carbon-yl]naph-thalen-1-yl}(naphthalen-1-yl)methanone.

In the title compound, C36H28O4, the 1-naphthoyl groups at the 1- and 8-positions of the central 2,7-dieth-oxy-naphthalene ring system are aligned almost anti-parallel and make a dihedral angle of 76.59 (4)°. The dihedral angles between the central 2,7-dieth-oxy-naphthalene ring system and the terminal naphthalene ring systems are 86.48 (4) and 83.97 (4)°. In the crystal, C-H⋯π inter-actions between the central naphthalene ring systems and the naphthoyl groups are observed along the a axis, with the mol-ecules forming a columnar structure. The columns are linked into chains parallel to the b axis by C-H⋯O inter-actions.

1,8-Bis(4-fluoro-benzo-yl)naphthalen-2,7-diyl dimethane-sulfonate.

The mol-ecule of the title compound, C26H18F2O8S2, lies across a crystallographic twofold rotation axis. The benzene rings of the 4-fluorobenzoyl groups make dihedral angles of 78.93 (12)° with the naphthalene ring system. An intra-molecular C-H⋯π inter-action occurs. In the crystal, a number of C-H⋯O inter-actions link the mol-ecules, forming a three-dimensional structure.

Bis(1-benzoyl-7-meth-oxy-naphthalen-2-yl) terephthalate.

The title molecule, C44H30O8, lies about a crystallographic inversion centre located at the centre of the central benzene ring. The benzene rings in the benzoyl and the terephthalate units make dihedral angles of 67.05 (7)° and 57.57 (7)°, respectively, with the naphthalene ring system. There is an intra-molecular C-H⋯O inter-action between the ketonic carbonyl O atom and an H atom on the naphthalene ring system. In the crystal, C-H⋯O inter-action of the benzene ring in the benzoyl group and weak C=O⋯π inter-action [O⋯centroid = 3.375 (2) Å] of the naphthalene ring with the O atom in the ketonic carbonyl group are observed. These inter-actions form layers parallel to the bc plane.

[2,7-Dieth-oxy-8-(4-fluoro-benzo-yl)naphthalen-1-yl](4-fluoro-phen-yl)methanone.

In the mol-ecule of the title compound, C28H22F2O4, the benzoyl groups are aligned almost anti-parallel and the fluorobenzene rings form a dihedral angle of 14.12 (7)°. The dihedral angles between the 2,7-dieth-oxy-naphthalene ring system and the benzene rings are 70.00 (4) and 67.28 (4)°. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯F hydrogen bonds, forming layers parallel to the ab plane. The layers are further connected by π-π inter-actions [centroid-centroid distances of 3.6115 (10) Å] into a three-dimensional structure.

(4-Eth-oxy-benzo-yl)[8-(4-eth-oxy-benzo-yl)-2,7-di-meth-oxy-naphthalen-1-yl]methanone.

The title mol-ecule, C30H28O6, possesses crystallographically imposed twofold symmetry, with two central C atoms in the naphthalene unit lying on the rotation axis along [001]. The 4-eth-oxy-benzoyl groups at the peri positions of the naphthalene ring system are disordered over two sets of sites with occupancies of 0.769 (4) and 0.231 (4). They are directed in opposite directions from the naphthalene plane (anti orientation). For the major component, the dihedral angle between the aroyl benzene ring and the naphthalene ring system is 75.62 (13)° [minor component 75.5 (4)°], and that between the aroyl benzene rings is 32.58 (15)°. In the crystal, mol-ecules are linked via C-H⋯O and C-H⋯π inter-actions, forming a three-dimensional network.

(2,7-Di-meth-oxy-naphthalen-1-yl)(naph-thalen-1-yl)methanone.

The asymmetric unit of the title compound, C23H18O3, contains two independent mol-ecules (A and B). Each mol-ecule has essentially the same conformation (r.m.s. deviation of fitted mol-ecules = 0.173 Å) with the aromatic rings twisted in a near perpendicular manner. The dihedral angles between the two naphthalene ring systems are 79.07 (4) and 88.19 (4)° in the two independent mol-ecules. In the crystal, the A mol-ecules are connected by C-H⋯O inter-actions, forming chains along the b-axis direction. Further C-H⋯O inter-actions between the H atoms of the meth-oxy group and the O atoms of the carbonyl units link the A and B mol-ecules, forming a three-dimensional network.