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Crystal structure and Hirshfeld surface analysis of 2-{[7-acetyl-4-cyano-6-hy-droxy-8-(4-meth-oxy-phen-yl)-1,6-dimethyl-5,6,7,8-tetra-hydro-iso-quino-lin-3-yl]sulfan-yl}-N-phenyl-acetamide.

ABSTRACT: The title mol-ecule, C₂₉H₂₉N₃O₄S, adopts a conformation with the two phenyl substituents disposed on opposite sides of the mean plane of the iso-quinoline unit. In the crystal, corrugated layers of mol-ecules are formed by N-H⋯O, C-H⋯N and C-H⋯S hydrogen bonds together with C-H⋯π(ring) inter-actions. These layers are connected by C-H⋯O contacts. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (45.2%), C⋯H/H⋯C (20.2%), O⋯H/H⋯O (15.8%) and N⋯H/H⋯N (11.0%) inter-actions.

SUBMITTER: Sayed EM

PROVIDER: S-EPMC8183441 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystallographic and spectroscopic characterization of 2-[(7-acetyl-4-cyano-6-hy-droxy-1,6-dimethyl-8-phenyl-5,6,7,8-tetra-hydro-isoquinolin-3-yl)sulfan-yl]-<i>N</i>-phenyl-acetamide.

Project description:In the title mol-ecule, C28H27N3O3S, the heterocyclic portion of the tetra-hydro-iso-quinoline unit is planar and an intra-molecular N-H⋯N hydrogen bond and a C-H⋯π(ring) inter-action help to determine the overall conformation. In the crystal, a layer structure with the layers parallel to (10) is generated by O-H⋯O and C-H⋯O hydrogen bonds.

| S-EPMC7869536 | biostudies-literature

Crystal structure of N-[4-amino-5-cyano-6-(methyl-sulfan-yl)pyridin-2-yl]-2-(cyclo-hexyl-sulfan-yl)acetamide.

Project description:In the title mol-ecule, C15H20N4OS2, the acetamido fragment is nearly coplanar with the pyridyl ring [C-N-C-C torsion angle = -4.1?(2)°], while the cyclo-hexyl-sulfanyl portion protrudes from this plane [N-C-C-S torsion angle = -40.8?(6)°]. In the crystal, alternating pairwise N-H?O and N-H?N hydrogen bonds across inversion centres form chains along [101], which are associated into stepped layers via offset ?-? stacking between pyridyl rings [centroid-centroid distance = 3.566?(1)?Å]. The cyclo-hexyl group and the two atoms of the S-C bond attached to it are disordered over two sets of sites with site-occupancy factors of 0.8845?(18) and 0.1155?(18).

| S-EPMC4186101 | biostudies-literature

Crystal structure of N-[4-amino-5-cyano-6-(methyl-sulfan-yl)pyridin-2-yl]acetamide hemihydrate.

Project description:The title compound, C9H10N4OS·0.5H2O, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit, together with a water mol-ecule of crystallization. The acetamide moiety, which has an extended conformation, is inclined to the pyridine ring by 7.95?(16)° in mol-ecule A and by 1.77?(16)° in mol-ecule B. In the crystal, the A and B mol-ecules are linked by two N-H?Ocarbon-yl hydrogen bonds, forming a dimer. The dimers are linked via N-H?N hydrogen bonds, forming ribbons that are linked by N-H?Owater hydrogen bonds to form sheets parallel to (110). The sheets are linked by O-H?N hydrogen bonds, forming slabs, and between the slabs there are weak slipped parallel ?-? inter-actions [inter-centroid distance = 3.734?(2)?Å, inter-planar distance = 3.3505?(11)?Å and slippage = 1.648?Å], forming a three-dimensional structure.

| S-EPMC4350750 | biostudies-literature

Crystal structure of N-[4-amino-5-cyano-6-(methyl-sulfan-yl)pyridin-2-yl]-2-chloro-acetamide.

Project description:In the title compound, C9H9ClN4OS, the dihedral angle between the acetamide moiety and the pyridine ring is 4.83?(12)°. The O=C-C-Cl torsion angle is 46.4?(3)° and an intra-molecular C-H?O inter-action generates an S(6) ring. In the crystal, mol-ecules are linked by N-H?O, N-H?N and C-H?N hydrogen bonds, generating sheets lying parallel to (120).

| S-EPMC4350726 | biostudies-literature

Crystal structures and Hirshfeld surface analyses of 2-[(4,6-di-amino-pyrimidin-2-yl)sulfan-yl]-N-(pyridin-2-yl)acetamide and 2-[(4,6-di-amino-pyrimidin-2-yl)sulfan-yl]-N-(pyrazin-2-yl)acetamide.

Project description:In the title compounds, C11H12N6OS (I) and C10H11N7OS (II), the di-amino-pyrimidine ring makes dihedral angles of 71.10?(9)° with the pyridine ring in (I) and 62.93?(15)° with the pyrazine ring in (II). The ethanamine group, -CH2-C(=O)-NH- lies in the plane of the pyridine and pyrazine rings in compounds (I) and (II), respectively. In both compounds, there is an intra-molecular N-H?N hydrogen bond forming an S(7) ring motif and a short C-H?O inter-action forming an S(6) loop. In the crystals of both compounds, mol-ecules are linked by pairs of N-H?N hydrogen bonds, forming inversion dimers with R22(8) ring motifs. In (I), the dimers are linked by N-H?O and N-H?N hydrogen bonds, forming layers parallel to (1[Formula: see text] [Formula: see text]). The layers are linked by offset ?-? inter-actions [inter-centroid distance = 3.777?(1)?Å], forming a three-dimensional supra-molecular structure. In (II), the dimers are linked by N-H?O, N-H?N and C-H?O hydrogen bonds, also forming a three-dimensional supra-molecular structure.

| S-EPMC5947495 | biostudies-literature

Crystal structure, Hirshfeld surface analysis and computational study of 2-chloro-N-[4-(methyl-sulfan-yl)phen-yl]acetamide.

Project description:In the title compound, C9H10ClNOS, the amide functional group -C(=O)NH- adopts a trans conformation with the four atoms nearly coplanar. This conformation promotes the formation of a C(4) hydrogen-bonded chain propagating along the [010] direction. The central part of the mol-ecule, including the six-membered ring, the S and N atoms, is fairly planar (r.m.s. deviation of 0.014). The terminal methyl group and the C(=O)CH2 group are slightly deviating out-of-plane while the terminal Cl atom is almost in-plane. Hirshfeld surface analysis of the title compound suggests that the most significant contacts in the crystal are H?H, H?Cl/Cl?H, H?C/C?H, H?O/O?H and H?S/S?H. ?-? inter-actions between inversion-related mol-ecules also contribute to the crystal packing. DFT calculations have been performed to optimize the structure of the title compound using the CAM-B3LYP functional and the 6-311?G(d,p) basis set. The theoretical absorption spectrum of the title compound was calculated using the TD-DFT method. The analysis of frontier orbitals revealed that the ?-?* electronic transition was the major contributor to the absorption peak in the electronic spectrum.

| S-EPMC7133040 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 2-[(1,3-benzoxazol-2-yl)sulfan-yl]-N-(2-meth-oxy-phen-yl)acetamide.

Project description:In the title compound, C16H14N2O3S, the 1,3-benzoxazole ring system is essentially planar (r.m.s deviation = 0.004?Å) and makes a dihedral angle of 66.16?(17)° with the benzene ring of the meth-oxy-phenyl group. Two intra-molecular N-H?O and N-H?N hydrogen bonds occur, forming S(5) and S(7) ring motifs, respectively. In the crystal, pairs of C-H?O hydrogen bonds link the mol-ecules into inversion dimers with R 2 2(14) ring motifs, stacked along the b-axis direction. The inversion dimers are linked by C-H?? and ?-?-stacking inter-actions [centroid-to-centroid distances = 3.631?(2) and 3.631?(2)?Å], forming a three-dimensional network. Two-dimensional fingerprint plots associated with the Hirshfeld surface show that the largest contributions to the crystal packing come from H?H (39.3%), C?H/H?C (18.0%), O?H/H?O (15.6) and S?H/H?S (10.2%) inter-actions.

| S-EPMC6775743 | biostudies-literature

N-[4-(9-Chloro-quino[3,2-b]benzo[1,4]thia-zin-6-yl)but-yl]acetamide.

Project description:In the title mol-ecule, C21H20ClN3OS, the tetra-cyclic system is close to planar [r.m.s. deviation = 0.110 (4) Å]. The dihedral angle between the quinoline ring system and the benzene ring is 178.3 (1)° and the angle between two (S-C=C-N) halves of the thia-zine ring is 173.4 (1)°. In the crystal, mol-ecules are arranged via π-π inter-actions [centroid-centroid distances = 3.603 (2)-3.739 (2) Å] into slipped stacks extending along [010]. Inter-molecular N-H⋯O hydrogen bonds link the amide groups of neighbouring mol-ecules along the stack, generating a C(4) motif. The title compound shows promising anti-proliferative and anti-cancer activity.

| S-EPMC3588930 | biostudies-literature

Crystal structure of bis-(3-bromo-mesit-yl)(quino-lin-1-ium-8-yl)boron(III) tribromide.

Project description:The title compound, C27H26.82BBr2.18N(+)·Br3 (-), is a cationic tri-aryl-borane isolated as its tribromide salt. The aryl substituents include a protonated 8-quinolyl group and two 3-bromo-mesityl groups. The mol-ecule was prepared on combination of 3:1 Br2 and dimesit-yl(quinolin-8-yl)borane in hexa-nes. The refinement of the structure indicated a degree of 'over-bromination' (beyond two bromine atoms) for the cation. There are two tribromide ions in the asymmetric unit, both completed by crystallographic inversion symmetry.

| S-EPMC4555423 | biostudies-literature

N-Cyclo-hexyl-2-(2,3-dichloro-phenyl-sulfan-yl)acetamide.

Project description:In the crystal structure of title compound, C(14)H(17)Cl(2)NOS, the cyclo-hexyl ring has a chair conformation and connects with an equatorial N atom. Mol-ecules are connected via N-H⋯O hydrogen bonds into chains.

| S-EPMC2967950 | biostudies-literature

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