Outer Benzene Research Articles

Catena-Poly[[silver(I)-μ-[9,10-bis(1H-benzimidazol-1-ylmethyl)anthracene]-κ2N3:N3′] bis(nitrato-κO)silver(I)

Yellow needle-shaped crystals of the title compound, {[Ag(C(30)H(22)N(4))][Ag(NO(3))(2)]}(n), were obtained by the reaction of AgNO(3) and 9,10-bis(benzimidazol-1-ylmethyl)anthracene (L) in a 2:1 ratio. The asymmetric unit consists of two Ag(I) cations, one half L ligand and one nitrate anion. One Ag(I) cation occupies a crystallographic inversion centre and links two N-atom donors of two distinct L ligands to form an infinite one-dimensional coordination polymer. The second Ag(I) cation lies on a crystallographic twofold axis and is coordinated by two O-atom donors of two nitrate anions to form an [Ag(NO(3))(2)](-) counter-ion. The polymeric chains are linked into a supramolecular framework via weak Ag···O [3.124 (5) Å] and Ag···π (2.982 Å) interactions (π is the centroid of an outer anthracene benzene ring). The π interactions contain two short Ag···C contacts [2.727 (6) and 2.765 (6) Å], which can be considered to define Ag-η(2)-anthracene bonding interactions. In comparison with a previously reported binuclear Ag(I) complex [Du, Hu, Zhang, Zeng & Bu (2008). CrystEngComm, 10, 1866-1874], this new one-dimensional coordination polymer was obtained by changing the metal-ligand ratio during the synthesis.

Phenazin-5-ium bromide

In the title compound, C12H9N2 +·Br−, the protonated tricyclic ring system is slightly twisted, with a dihedral angle of 3.9 (1)° between the two outer benzene rings. In the crystal, N—H⋯Br and C—H⋯Br hydrogen bonds link two cations and two bromide anions into centrosymmetric assemblies, which are further packed into stacks along [010] via π–π inter­actions between the aromatic rings [centroid–centroid distance = 3.725 (4) Å].

(11R,12S)-16-Amino-tetra-cyclo-[6.6.2.0(2,7).0(9,14)]hexa-deca-2(7),3,5,9(14),10,12-hexaen-15-ol.

In the title compound, C16H15NO, the dihedral angle between the outer benzene rings is 51.88 (6)°, and each of the central six-membered rings has a boat conformation. The hy­droxy and amino groups are syn, and the hy­droxy H atom forms an intra­molecular O—H⋯N hydrogen bond. In the crystal, mol­ecules assemble via C—H⋯O and C—H⋯π inter­actions, consolidating a three-dimensional architecture.

9,9-Dibutyl-9H-fluorene-2-carbonitrile.

The fluorene fragment of the title compound, C22H25N, is essentially planar, with an r.m.s deviation of the five-membered ring of 0.005 (2) Å. The dihedral angle between this ring and the outer benzene rings are 1.5 (2) and 0.7 (2)° while that between the benzene rings is 2.1 (2)°. The cyano group makes an angle of 0.3 (2)° with the attached benzene ring.

Bis(3,5-dimethyl-1H-pyrazole-κN2)bis(3,3′′,5,5′′-tetramethyl-[1,1′:3′,1′′-terphenyl]-2′-carboxylato-κO)iron(II) dichloromethane monosolvate

In the title compound, [Fe(C23H21O2)2(C5H8N2)2]·CH2Cl2, the Fe2+ cation is coordinated by the N atoms of two 3,5-dimethyl­pyrazole ligands and the carboxyl­ate O atoms from two tetra­methyl­terphenyl­carboxyl­ate ligands, forming an FeN2O2 polyhedron with a slightly distorted tetra­hedral coordination geometry. Intra­molecular N—H⋯O and C—H⋯O hydrogen-bonding inter­actions stabilize the mol­ecular conformation. The dihedral angles formed by the central benzene ring with the outer benzene rings of the terphenyl groups are 47.92 (8), 59.38 (8), 48.24 (8) and 52.37 (8)°. The dichloro­methane solvent mol­ecule inter­acts with the complex mol­ecule via a C—H⋯O hydrogen bond. In the crystal, centrosymmetrically related complex mol­ecules are linked into dimers through pairs of C—H⋯O hydrogen bonds.

4,4′-[(5-Carboxy-1,3-phenylene)bis(oxy)]dibenzoic acid

In the title compound, C21H14O8, the central benzene ring makes dihedral angles of 77.8 (6) and 75.9 (5)° with the outer benzene rings. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds involving carboxyl groups, forming one-dimensional ladders. Two-dimensional layers are formed by inter­penetration of these one-dimensional ladders.

N-Acetyl-N-[2,4-dicyano-1-(4-methoxyphenyl)-9,10-dihydrophenanthren-3-yl]acetamide

In the title compound, C27H21N3O3, the cyclo­hexa-1,3-diene ring has a screw-boat conformation, and the fused ring system is folded, the dihedral angle between the outer benzene rings being 27.61 (6)°. The N-acetyl­acetamide residue (r.m.s. deviation = 0.0935 Å) has an anti conformation and is essentially perpendicular to the benzene ring to which it is connected [dihedral angle = 89.14 (6)°]; the meth­oxy­benzene group is also twisted out of this ring [dihedral angle = 59.47 (7)°]. The three-dimensional architecture is consolidated by C—H⋯O and C—H⋯π inter­actions.

3-Amino-1-(thiophen-2-yl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile

In the title compound, C20H13N3S, the partially saturated ring adopts a twisted half-boat conformation with the methyl­ene C atom closest to the amino­benzene ring lying 0.690 (6) Å out of the plane defined by the five remaining atoms. The dihydro­phenanthrene residue has a folded conformation [dihedral angle between the outer benzene rings = 26.27 (18)°]. The thio­phen-2-yl ring forms a dihedral angle of 63.76 (19)° with the benzene ring to which it is attached. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R 2 2(12) loops. The dimers are linked into layers in the bc plane by weak C—H⋯π inter­actions. The thio­phen-2-yl ring is disordered over two essentially coplanar but opposite orientations in a 0.918 (4):0.082 (4) ratio.

Fluphenazine dihydrochloride dimethanol solvate

In the title compound {systematic name: 1-(2-hy­droxy­eth­yl)-4-[3-(2-trifluoro­methyl-10H-phenothia­zin-10-yl)prop­yl]piperazine-1,4-diium dichloride dimethanol disolvate}, C22H28F3N3OS2+·2Cl−·2CH3OH, the dihedral angle between the planes of the two outer benzene rings of the tricyclic phenothia­zine system is 46.91 (13)°. The piperazine ring adopts a chair conformation. The crystal structure is stabilized by O—H⋯Cl, N—H⋯Cl, C—H⋯O, C—H⋯Cl and C—H⋯F hydrogen bonds and contacts.

4-(4-Methoxyphenyl)naphtho[2,3-b]thiophene

In the title compound, C19H14OS, the naphtho­thio­phene moiety is almost planar except for the S atom of the five-membered ring, which is situated 0.047 (6) Å out of the C4 plane (with an r.m.s. deviation of fitted atoms = 0.0009 Å). The dihedral angle between the naphtho­thio­phene plane and the attached meth­oxy­phenyl ring is 67.6 (2)°. In the crystal, a C—H⋯π inter­action is observed between a meth­oxy­phenyl C—H group and the outer benzene ring of the naphtho­thio­phene moiety. The five-membered ring of the naphtho­thio­phene moiety is disordered, with the S and opposite non-fused C atom approximately exchanging positions, with a site-occupancy factors of 0.808 (3) and 0.187 (3).

10-(4-Methylbenzylidene)anthracen-9(10H)-one

In the title compound, C22H16O, the six-membered ring within the anthrone moiety adopts a shallow boat conformation, with puckering parameters Q = 0.2860 (17) Å, Θ = 99.1 (3)° and Φ = 114.8 (3)°. The dihedral angle between the outer benzene rings is 26.53 (8)°. The mean plane through the anthrone ring system makes a dihedral angle of 38.73 (6)° with the pendant benzene ring. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds into zigzag chains propagating along the c-axis direction and weak C—H⋯π inter­actions further consolidate the structure.

N,N′-Bis(4-methylbenzylidene)benzene-1,4-diamine

The centrosymmetric title compound, C22H20N2, crystallizes with one half-mol­ecule in the asymmetric unit. The dihedral angle between the central and outer benzene rings is 46.2 (2)°.

{2,2′-[o-Phenylenebis(nitrilomethanylylidene)]diphenolato-κ4O,N,N′,O′}nickel(II) monohydrate

The NiII atom in the title monohydrate, [Ni(C20H14N2O2)]·H2O, is coordinated within a cis-N2O2 square-planar donor set provided by the tetra­dentate Schiff base ligand. Overall, the mol­ecule has a curved shape with the dihedral angle formed between the planes of the outer benzene rings being 13.92 (18)°. The water mol­ecule was found to be disordered over two positions [ratio 0.80 (1):0.20 (1)] and the major component is linked to the complex via an O—H⋯O hydrogen bond.

5-(Biphenyl-4-yl)-3-(3-methoxybenzylidene)furan-2(3H)-one

In the title compound, C24H18O3, the dihedral angles between the mean planes of the five-membered furan ring and the meth­oxy-substituted benzene and the adjacent and outer biphenyl benzene rings are 2.43 (7), 4.48 (7) and 30.47 (8)°, respectively. The crystal packing is stabilized by weak C—H⋯O and C—H⋯π inter­molecular hydrogen bonds and π–π stacking inter­actions [centroid–centroid distances = 3.8752 (8) and 3.8331 (8) Å].

2-[N-(4-{4-[(E)-(2-Hydroxybenzylidene)amino]phenoxy}phenyl)carboximidoyl]phenol

The mol­ecular structure of the title Schiff base compound, C26H20N2O3, shows that respective methyl­idene residues are almost coplanar with the adjacent terminal benzene ring owing to the presence of intra­molecular O—H⋯N hydrogen bonds [the N—C—C—C torsion angles are −6.6 (7) and −6.7 (7)°]. However, twists are exhibited about each methyl­idene and respective benzene ring connected to the central O atom; the dihedral angles formed between the two inner and two outer benzene rings are 54.6 (2) and 45.6 (3)°, respectively. The conformation about each of the C=N bonds [1.285 (5) and 1.295 (5) Å] is E. In the crystal, extensive C—H⋯π contacts involving all benzene rings results in the formation of layers in the ac plane.

3,3′-Dimethoxy-2,2′-[(4,5-dimethyl-o-phenylene)bis(nitrilomethanylylidene)]diphenol

The asymmetric unit of the title compound, C24H24N2O4, comprises two crystallographically independent mol­ecules A and B. The dihedral angles between the central dimethyl-substituted benzene ring and the two outer benzene rings are 49.5 (1) and 5.06 (11)° in mol­ecule A, and 42.55 (8) and 5.77 (9)° in mol­ecule B. In each mol­ecule, two strong intra­molecular O—H⋯N hydrogen bonds generate two S(6) ring motifs. The crystal structure is further stabilized by inter­molecular π–π [centroid–centroid distances of 3.591 (1)–3.876 (1) Å] inter­actions.

1-[5-(Anthracen-9-yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone.

In the title compound, C25H20N2O, the pyrazoline ring is nearly planar [maximum atomic deviation = 0.0254 (17) Å]; but the anthracene ring system is distorted from a coplanar structure [maximum atomic deviation = 0.181 (3) Å], the dihedral angle between the outer benzene rings being 10.68 (13)°. The pyrazoline ring is almost perpendicular to the mean plane of the anthracene ring system [dihedral angle = 76.94 (8)°], but nearly coplanar with the phenyl ring [dihedral angle = 1.63 (7)°]. π–π stacking is observed between parallel benzene rings of adjacent anthracene units, the face-to-face distance being 3.27 (3) Å. Weak intra­molecular C—H⋯N hydrogen bonding also occurs.

3-(4-Fluorophenylsulfonyl)-2-methylnaphtho[1,2-b]furan

In the title compound, C19H13FO3S, the 4-fluoro­phenyl ring makes a dihedral angle of 68.59 (5)° with the mean plane of the naphtho­furan fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O, C—H⋯F and C—H⋯π inter­actions. The crystal structure also exhibits aromatic π–π inter­actions between the central benzene and the outer benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.650 (3) Å].

2,3-Dibromo-1-[4-(2,3-dibromo-4,5-dimethoxybenzyl)-2,5-dimethoxybenzyl]-4,5-dimethoxybenzene

The mol­ecule of the title compound, C26H26Br4O6, is located around a crystallographic inversion center. The dihedral angle between the central benzene ring and the outer benzene ring is 89.26 (1)°.

{6,6′-Diethoxy-2,2′-[4,5-dimethyl-o-phenylenebis(nitrilomethylidyne)]diphenolato}copper(II)

In the title complex, [Cu(C26H26N2O4)], the CuII ion lies on a crystallographic twofold rotation axis and is coordinated in a slightly distorted square-planar environment. The dihedral angle between the central benzene ring and each of the two symmetry-related outer benzene rings is 5.1 (2)°. The crystal structure is stabilized by inter­molecular π–π inter­actions with centroid–centroid distances in the range 3.466 (2)–3.6431 (16) Å.