6-Phenyl-benzo[d]naphtho-[2,3-b]thio-phene.

In the title compound, C22H14S, the r.m.s. deviation from the mean plane of the four-fused-ring naphtho-thio-phene unit is 0.056 Å. The dihedral angle between the naphtho-thio-phene plane and the pendant phenyl ring is 67.24 (6)°. In the crystal, weak C-H⋯π and π-π stacking [minimum centroid-centroid separation = 3.7466 (10) Å] inter-actions are observed, which together lead to (010) sheets.

2-Hy-droxy-4-(prop-2-yn-yloxy)benz-alde-hyde.

The asymmetric unit of the title compound, C10H8O3, contains two independent mol-ecules, both of which are almost planar (r.m.s deviations for all non-H atoms of 0.044 and 0.053 Å). The dihedral angles between the benzene ring and the prop-1-yne group are 3.47 (1) and 3.07 (1)° in the two mol-ecules, and the prop-1-yne groups adopt extended conformations. In each mol-ecule, an intra-molecular O-H⋯O hydrogen bond involving the OH and aldehyde substituents forms an S(6) ring. In the crystal, mol-ecules are linked into cyclic centrosymmetric dimers via C-H⋯O hydrogen bonds, generating R2(2)(14) ring motifs. The crystal structure is further stabilized by aromatic π-π stacking inter-actions between the benzene rings [centroid-centroid distances = 3.813 (2) and 3.843 (2) Å].

2,4-Bis[(prop-2-yn-yl)-oxy]benzaldehyde.

In the title compound, C(13)H(10)O(3), two prop-2-yn-yloxy groups are attached to the benzaldehyde ring at positions 2 and 6. The crystal packing features C-H⋯O inter-actions.

DFT simulations and vibrational analysis of FTIR and FT-Raman spectra of 2-amino-4-methyl benzonitrile.

This work deals with the vibrational spectroscopy of 2-amino-4-methyl benzonitrile (AMB) by means of quantum chemical calculations. The mid and far FTIR and FT-Raman spectra were measured in the condensed state. Hartree-Fock (HF/6-31G(*)) and density functional theory (DFT, B3LYP/6-31G(*)) ab initio methods have been performed to interpret the observed vibrational spectra. The vibrational spectra were interpreted with the aid of normal coordinate analysis based on scaled density functional force field. The results of the calculations were applied to simulated infrared and Raman spectra of the title compound, which showed excellent agreement with the observed spectra.

6-(4-Meth-oxy-phen-yl)naphtho[2,3-b][1]benzothio-phene.

The asymmetric unit of the title compound, C23H16OS, contains two independent mol-ecules with opposite orientations of the meth-oxy groups bonded to the benzene rings. The napthobenzothiophene group in the two molecules is separated by an average distance of 3.912 Å. In both mol-ecules, the napthobenzothio-phene unit is almost planar, with r.m.s deviations of 0.0522 and 0.0143 Å. The meth-oxy-phenyl ring makes dihedral angles of 67.0 (6)° and 70.4 (6)° with respect to the napthobenzothio-phene ring system in the two mol-ecules. The crystal packing features C-H⋯S, π-π [centroid-centroid distances = 3.666 (10) and 3.658 (10) Å] and C-H⋯π inter-actions, forming a sheet running along the b-axis direction.

9-(4-Meth-oxy-phen-yl)anthracene.

In the title compound, C21H16O, the dihedral angle between the anthracene ring system and the benzene ring is 74.3 (5)°. The anthracene ring system is essentially planar (r.m.s. deviation = 0.0257 Å) and the meth-oxy group lies in the plane of the benzene ring [C1-O1-C2-C7 torsion angle = 0.5 (2)°]. The crystal structure features π-π [centroid-centroid distance = 3.9487 (12) Å] and C-H⋯π inter-actions, forming a sheet running along the a-axis direction.

(Biphenyl-4-yl)[2-(4-methyl-benzo-yl)phen-yl]methanone.

In the title compound, C(27)H(20)O(2), the central benzene ring makes dihedral angles of 64.86 (7) and 70.35 (7)° with the methyl-substituted ring and the biphenyl ring system, respectively. The crystal packing is stabilized by inter-molecular C-H⋯O inter-actions, which link the mol-ecules into chains parallel to the b axis.

(4-Methyl-phen-yl)[2-(thio-phen-2-ylcarbon-yl)phen-yl]methanone.

The crystal studied of the title compound, C(19)H(14)O(2)S, was an inversion twin with a 0.7 (1):0.3 (1) domain ratio. The central benzene ring makes dihedral angles of 63.31 (9) and 60.86 (9)°, respectively, with the 4-methyl-phenyl and thio-phene rings. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds and S⋯π [3.609 (3) Å] inter-actions.

3-(2-Meth-oxy-naphthalen-1-yl)-2-benzofuran-1(3H)-one.

The asymmetric unit of the title compound, C(19)H(14)O(3), contains two crystallographically independent mol-ecules in which the dihedral angles between the naphthalene and benzofuran ring systems are 76.49 (7) and 86.17 (7)°. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O hydrogen-bonding inter-actions into chains running parallel to the a axis. In addition, the crystal packing is stabilized by C-H⋯π inter-actions.