Crystal structure and Hirshfeld surface analysis and energy frameworks of 1-(2,4-di-methyl-phen-yl)-4-(4-meth-oxy-phen-yl)naphthalene.

In the title compound, C25H22O, the two rings of the naphthalene system are inclined to each other by 3.06 (15)°. The mean plane of the naphthalene ring system makes a dihedral angle of 65.24 (12)° with the di-methyl-phenyl ring and 55.82 (12)° with the meth-oxy-phenyl ring. The di-methyl-phenyl ring is inclined to the meth-oxy-phenyl ring by 59.28 (14)°. In the crystal, adjacent mol-ecules are linked via C-H⋯π inter-actions, forming chains along [100]. Using Hirshfeld surface and two-dimensional fingerprint plots, the presence of short inter-molecular inter-actions in the crystal structure were analysed. The inter-molecular inter-action energies were also calculated and their distribution over the crystal structure was visualized graphically using energy frameworks.

Crystal structure of (E)-2-(4-meth-oxy-styr-yl)-3-methyl-1-phenyl-sulfonyl-1H-indole.

In the title compound, C24H21NO3S, the dihedral angles between the indole ring system (r.m.s. deviation = 0.030 Å) and the sulfur and ethyl-ene-bonded benzene rings are 80.2 (2) and 49.29 (15)°, respectively. The dihedral angle between the pendant benzene rings is 37.7 (2)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds and weak C-H⋯π and π-π [centroid-to-centroid distances = 3.549 (2) and 3.743 (3) Å] inter-actions, forming a three-dimensional network.

Crystal structure of ethyl 2-phenyl-9-phenyl-sulfonyl-9H-carbazole-3-carboxyl-ate.

In the title compound, C27H21NO4S, the dihedral angles between the carbazole ring system (r.m.s. deviation = 0.015 Å) and the sulfur-bonded and directly linked benzene rings are 79.98 (11) and 53.51 (18)°, respectively. The benzene rings subtend a dihedral angle of 48.4 (2)°. The ethyl side chain of the ester group has an extended conformation [C-O-C-C = -172.3 (3)°]. In the crystal, inversion dimers linked by pairs of weak C-H⋯O hydrogen bonds generate R 2 (2)(22) loops. The dimers are linked by weak C-H⋯π and π-π [centroid-to-centroid distances ranging from 3.5042 (14) to 3.888 (2) Å] inter-actions, thereby forming a three-dimensional supra-molecular network.

Crystal structure of N-{[3-bromo-1-(phenyl-sulfon-yl)-1H-indol-2-yl]meth-yl}benzene-sulfonamide.

In the title compound, C21H17BrN2O4S2, the indole ring system subtends dihedral angles of 85.96 (13) and 9.62 (16)° with the planes of the N- and C-bonded benzene rings, respectively. The dihedral angles between the benzene rings is 88.05 (17)°. The mol-ecular conformation is stabilized by intra-molecular N-H⋯O and C-H⋯O hydrogen bonds and an aromatic π-π stacking [centroid-to-centroid distance = 3.503 (2) Å] inter-action. In the crystal, short Br⋯O [2.9888 (18) Å] contacts link the mol-ecules into [010] chains. The chains are cross-linked by weak C-H⋯π inter-actions, forming a three-dimensional network.

Crystal structure of (2-methyl-1-phenyl-sulfon-yl-1H-indol-3-yl)(phen-yl)methanone.

In the title compound, C22H17NO3S, the sulfonyl-bound phenyl ring is almost orthogonal to the indole ring system, making a dihedral angle of 84.89 (7)°. The carbonyl-bound phenyl ring forms a dihedral angle of 57.32 (5)° with the indole ring system. The two phenyl rings are inclined at 52.68 (7)°. The S atom has a distorted tetra-hedral configuration. In the crystal, weak C-H⋯O inter-actions link the mol-ecules, forming a helical chain along the b-axis direction.

Crystal structure of (2-bromo-methyl-1-phenyl-sulfonyl-1H-indol-3-yl)(phen-yl)methanone.

In the title compound, C22H16BrNO3S, the phenyl rings make dihedral angles of 84.81 (16) and 61.67 (17)° with the indole ring system (r.m.s. deviation = 0.012 Å), while the phenyl rings are inclined to one another by 69.5 (2)°. The mol-ecular structure is stabilized by weak intra-molecular C-H⋯O hydrogen bonds. The sulfonyl S atom has a distorted tetra-hedral configuration. In the crystal, there are no significant inter-molecular inter-actions present.

(E)-1-[2-(2-Nitro-styr-yl)-1-phenyl-sulfonyl-1H-indol-3-yl]propan-1-one.

In the title compound, C25H20N2O5S, the phenyl ring makes dihedral angles of 89.88 (8) and 13.98 (8)°, respectively, with the indole ring system and the nitro-benzene ring. The dihedral angle between the indole ring system and the nitro-benzene ring is 88.48 (11)°. The mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O inter-action. In the crystal, π-π inter-actions, with centroid-centroid distances of 3.6741 (18) and 3.8873 (17) Å, link the mol-ecules into layers parallel to the ab plane.

(E)-2-Bromo-1-[2-(2-nitro-styr-yl)-1-phenyl-sulfonyl-1H-indol-3-yl]ethanone.

In the title compound C24H17BrN2O5S, the phenyl ring makes dihedral angles of 85.4 (2) and 8.8 (2)° with the indole ring system and the nitro-benzene ring, respectively, while the indole ring system and nitrobenzene ring make a dihedral angle of 80.1 (2)°. In the crystal, weak C-H⋯O inter-actions link the mol-ecules, forming a two-dimensional network parallel to the bc plane.

2-Bromo-1-(1-phenyl-sulfonyl-1H-indol-3-yl)propan-1-one.

In the title compound, C17H14BrNO3S, the phenyl ring makes a dihedral angle of 89.78 (16)° with the plane of the indole ring system. The terminal Br atom and the methyl group are disordered over two sets of sites, with site occupancies of 0.860 (2) and 0.140 (2). In the crystal, mol-ecules are linked into a chain along the b-axis direction by weak C-H⋯O hydrogen bonds. The chains are further linked by C-H⋯π inter-actions, forming layers parallel to the bc plane.

Crystal structure of 2-(2,4-di-chloro-phen-yl)-4-hydroxy-9-phenyl-sulfonyl-9H-carbazole-3-carbaldehyde.

In the title compound, C25H15Cl2NO4S, the di-chloro-phenyl ring is twisted by 68.69 (11)° from the mean plane of the carbazole ring system [r.m.s. deviation = 0.084 (2)°]. The hy-droxy group is involved in an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) graph-set motif. In the crystal, pairs of C-H⋯Cl hydrogen bonds link mol-ecules into inversion dimers with an R (2) 2(26) motif. Weak C-H⋯O inter-actions further link these dimers into ribbons propagating in [100].

(Naphthalen-1-yl){2-[(5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]phenyl}methanone.

The title compound C28H22O2, basically consists of three ring systems, viz. a central benzene ring, with a lateral napthalene group to which it subtends a dihedral angle of 66.56 (4)° and a tetra-hydro-pyran ring exhibiting a half-chair conformation. The mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O inter-action, while the crystal packing features weak C-H⋯π contacts.

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.

(E)-1-[2-(4-Chloro-2-nitro-styr-yl)-1-phenyl-sulfonyl-1H-indol-3-yl]propan-1-one.

In the title compound, C25H19ClN2O5S, the phenyl ring forms dihedral angles of 79.62 (12) and 80.02 (13)° with the indole ring system and the benzene ring, respectively. The nitro group is twisted at an angle of 22.39 (11)° with respect to the attached benzene ring. In the crystal, mol-ecules assemble into double layers in the ab plane via C-H⋯O inter-actions.

(E)-1-[2-(4-Fluoro-2-nitro-styr-yl)-1-phenyl-sulfonyl-1H-indol-3-yl]propan-1-one.

In the title compound, C25H19FN2O5S, the substituted phenyl ring makes a dihedral angle of 12.26 (9)° with the indole ring system. The nitro group is twisted at an angle of 26.92 (8)° out of the plane of the ring to which it is attached. The mol-ecular structure is stabilized by weak C-H⋯O hydrogen bonds. In the crystal, weak C-H⋯O, C-H⋯F and π-π [centroid-centroid distance = 3.6645 (11) Å] inter-actions link the mol-ecules, forming a three-dimensional network.

(Z)-3-(1-Chloro-prop-1-en-yl)-2-methyl-1-phenyl-sulfonyl-1H-indole.

In the title compound, C18H16ClNO2S, the indole ring system forms a dihedral angle of 75.07 (8)° with the phenyl ring. The mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming a chain along [10-1]. C-H⋯π inter-actions are also observed, leading to a three-dimensional network.

1-(2-Bromo-meth-yl-1-phenyl-sulfonyl-1H-indol-3-yl)propan-1-one.

In the title compound, C18H16BrNO3S, the dihedral angle between the phenyl ring and the indole ring system is 89.91 (11)°. The mol-ecular structure features weak C-H⋯O and C-H⋯Br hydrogen bonds. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming chains along the a-axis direction. The chains are further linked by C-H⋯π inter-actions, forming a layer parallel to the ab plane.

4-(2-Benzoyl-benzoyl)-N,N-diphenyl-aniline.

The asymmetric unit of the title compound, C(32)H(23)NO(2), comprises two crystallographically independent mol-ecules. In both mol-ecules, the geometries about the N atoms deviate significantly from the ideal trigonal-planar geometry with bond-angle sums about the N atom of 359.32° in one mol-ecule and 359.86° in the other. The O atoms of the carbonyl groups are deviated significantly from the central benzene rings by 0.6747 (14) and -1.1223 (13) Šin one molecule and -0.6230 (13) and 1.1559 (12) Šin the other. In the diphenyl-aniline units, the terminal phenyl rings are almost orthogonal to each other, with dihedral angles of 89.79 (9) and 89.76 (9)°. The crystal structure features C-H⋯O and C-H⋯π inter-actions.

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.