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In the title compound, C13H9ClN2O, the dihedral angle between the acrylo­nitrile C=C—CN plane and the quilonine ring system is 71.3 (2)°. In the crystal, mol­ecules are linked by O—H...N hydrogen bonds, forming chains along [01-1]. The chains are linked into a three-dimensional network through C—H...N inter­actions.

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There are two independent mol­ecules (A and B) in the asymmetric unit of the title compound, C14H12ClNO3. The mean planes of the methyl ester unit (Cmeth­yl—O—C=O; r.m.s. deviation = 0.051 Å for mol­ecule A and 0.016 Å for mol­ecule B) and the chloro­quilonine ring system (r.m.s. deviation = 0.023 Å for mol­ecule A and 0.014 Å for mol­ecule B) form dihedral angles of 63.5 (1)° in mol­ecule A and 78.1 (1)° in mol­ecule B. The main difference between the two independent mol­ecules is reflected in the (H)O—C—C=C(H2) torsion angle which is −109.7 (2)° in mol­ecule A and 10.6 (2)° in mol­ecule B. An intra­molecular O—H...O hydrogen bond is observed in mol­ecule A. In the crystal, mol­ecules A and B are linked into pairs via bifurcated O—H...(N,Cl) hydrogen bonds and a weak C—H...O hydrogen bond links pairs of mol­ecules into chains along [100].

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In the title compound, C27H25ClN2O3, the methyl­pyrrolidine ring adopts an envelope conformation with the N atom at the flap. The mean plane of the pyrrolidine ring makes dihedral angles of 82.1 (1), 84.4 (1) and 79.8 (1)°, respectively, with the adjacent benzene ring, the mean plane of the indoline ring system and the phenyl ring. The mol­ecular structure is stabilized by intra­molecular C—H...O hydrogen bonds. In the crystal, mol­ecules are linked into chains along [101] by N—H...O hydrogen bonds. C—H...π inter­actions are observed between the chains.
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