2-[2-(Methylamino)benzoyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one

The title compound, C19H17N3O2, was obtained from fruits of Evodia Rutaecarpa. In the solid state, the dihedral angle between the 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one (tetrahydro-β-carbolinone) unit and the benzoyl ring is 61.46 (3)°. In the crystal, dimers are formed through intermolecular N—H⋯O hydrogen-bonding interactions. In addition, intramolecular N—H⋯O hydrogen bonds are also observed. C—H⋯π contacts connect the dimers, leading to the formation of a three-dimensional supramolecular network.


Comment
The title compound, C 19 H 17 N 3 O 2 , is a tetrahydro-beta-carbolinone derivative isolated from the fruits of Evodia rutaecarpa.
The tetrahydro-beta-carbolinone ring is a structural unit found in natural products. It possesses significant biological activities and plays an important role as an intermediate for the synthesis of more complex alkaloids and further functionalized polycyclic systems of biological interest (Yamada et al., 1986;Jokela et al., 1987;Vicente et al., 2008). Herein, the conformation of the title compound has been determined by single-crystal analysis and further confirmed by mp, IR, and NMR.
supplementary materials sup-2 Refinement All H atoms were located on the difference maps, and were treated as riding atoms with C/N-H distances of 0.93, 0.96, 0.97 and 0.86 Å, for aryl, methyl, methine and amino groups, respectively, with U iso (H) = 1.5U eq (methyl C-atoms) and 1.2U eq (non-methyl C-atoms). The hightest peak is located 0.62 Å from C1 and the deepest hole is located 0.96 Å from H11B. Fig. 1. The molecular structure of the tile compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Special details
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.