Crystal structure and Hirshfeld surface analysis of 2-{[7-acetyl-4-cyano-6-hydroxy-8-(4-methoxyphenyl)-1,6-dimethyl-5,6,7,8-tetrahydroisoquinolin-3-yl]sulfanyl}-N-phenylacetamide

The title molecule adopts a conformation with the two phenyl substituents disposed on opposite sides of the mean plane of the isoquinoline unit. In the crystal, corrugated layers of molecules are formed by N—H⋯O, C—H⋯N and C—H⋯S hydrogen bonds together with C—H⋯π(ring) interactions. These layers are connected by C—H⋯O contacts.

Tienopyridine derivatives show diverse pharmacological activities including antibacterial activity against a drug-resistant S. epidermidis clinical strain (Leal et al., 2008) and cytotoxic activity against human hepatocellular liver carcinoma (HepG2) (Hassan et al., 2013) and are used as antiplatelet drugs for the treatment of acute coronary syndromes (Peters et al., 2003). ISSN 2056-9890

Structural commentary
The title molecule adopts a conformation in which the C24-C29 phenyl group is on the same side of the mean plane of tetrahydroisoquinoline core as the O2-H2A hydroxy group, while the 4-methoxyphenyl group is situated on the opposite side ( Fig. 1). There is an intramolecular O2-H2AÁ Á ÁO1 hydrogen bond, which controls the orientation of the acetyl group. Puckering analysis (Cremer & Pople, 1975) shows that the conformation of the C1-C5/C9 ring is close to halfchair with the C2 atom as the flap. The mean planes of the C10-C15 and C24-C29 rings are inclined to that of the pyridine N1/C5-C9 ring by 77.17 (3) and 67.93 (5) , respectively. All bond lengths and angles appear normal for the given formulation.

Figure 2
View of a portion of one layer seen along the b-axis direction. N-HÁ Á ÁO, C-HÁ Á ÁN and C-HÁ Á ÁS hydrogen bonds are depicted, respectively, by dark-blue, light-blue and yellow dashed lines. C-HÁ Á Á(ring) interactions are depicted by green dashed lines.

Figure 3
View of portions of two layers showing their connection by C-HÁ Á ÁO hydrogen bonds (black dashed lines). Other intermolecular interactions are depicted as in Fig. 2.

Figure 1
The title molecule with the atom-labelling scheme and 50% probability ellipsoids. The intramolecular hydrogen bond is depicted by a dashed line.
shown in Figs. 4 and 5, respectively. The red spots on the Hirshfeld surface represent strong intermolecular interactions (
In the crystal of NAQRIJ, dimers are formed through complementary sets of inversion-related O-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds, which are further connected into zigzag chains by pairwise C-HÁ Á ÁN interactions that also form inversion dimers. In KUGLIK, the heterocyclic amines are alternately connected by hydrogen bonds thus forming syndiotactic polymeric chains. The hydrogen-bonding network of water molecules forms planes parallel to (100). In the crystal of DUSVIZ, molecules are linked via C-HÁ Á ÁO hydrogen bonds. For the major disorder component, they form   Table 2 Summary of short intermolecular contacts (Å ) in the title structure.

Contact
Distance Symmetry operation 2.47 Àx, 1 À y, 1 À z C(11) chains that propagate parallel to the a axis. In AKIVUO, a layer structure with the layers parallel to (101) is generated by O-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds. In ULUTAZ, the molecules are linked via N-HÁ Á ÁO and C-HÁ Á ÁN hydrogen bonds into a three-dimensional network. Furthermore, the crystal packing is dominated by C-HÁ Á Á contacts involving the phenyl H atoms. In CARCOQ, molecules are linked by an O-HÁ Á ÁO hydrogen bond, forming chains propagating along the a-axis direction. The chains are linked by C-HÁ Á ÁF hydrogen bonds, forming layers lying parallel to (001). In POPYEB, molecules are packed in a herringbone manner parallel to (103) and (103) via weak C-HÁ Á ÁO and C-HÁ Á Á(ring) interactions. In ENOCIU, various C-HÁ Á Á and C-HÁ Á ÁO bonds link the molecules together.
In NIWPAL, the molecules are linked by N-HÁ Á ÁO intermolecular hydrogen bonds involving the sulfonamide function to form an infinite two-dimensional network parallel to (001).

N-phenylacetamide
Crystal data where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.49 e Å −3 Δρ min = −0.20 e Å −3 Special details Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = -30.00 and 210.00°. The scan time was 20 sec/frame. Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. H-atoms attached to carbon were placed in calculated positions (C-H = 0.95 -1.00 Å) while that attached to oxygen was placed in a location derived from a difference map and its coordinates adjusted to give O-H = 0.87 %A. All were included as riding contributions with isotropic displacement parameters 1.2 -1.5 times those of the attached atoms.