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Crystal Structure, Conformation and Vibrational Analysis of a Mannich Base: 2-[(phenylamino) methyl]-isoindole-1,3-dione

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Abstract

The crystal structure of 2-[(phenylamino) methyl]-isoindole-1,3-dione, C15H12N2O2, crystallizes in the triclinic space group Pī with cell parameters of a = 7.1176 (2) Å, b = 8.5533 (3) Å, c = 10.9163 (4) Å, α = 95.937 (2)°, β = 102.975 (2)°, γ = 108.474 (2)°, V = 603.18 (4) Å3 and Z = 2. This indole derivative is a Mannich base in which a methyl group bridges the molecules of phthalimide and aniline molecules. The dihedral angle between the phthalimide and aniline is 75.47 (3)°. The molecules of the title compound forms a centrosymmetric hydrogen-bonded dimer through a pair of N–H···O hydrogen bonds. C–H···π and an extensive π···π interactions, in addition, stabilize the molecular structure. The compound presented here is V-shaped, the angle at the methyl bridge [N–C–N] being 115.04 (12)°. Present study reports the conformation and hydrogen bonding interactions which play an important role in biological functions. Vibration analysis complement the structure analysed.

Graphical Abstract

The crystal structure of 2-[(phenylamino) methyl]-isoindole-1,3-dione is a Mannich base compound in which a phenylamine and phthalimide molecules are bridged by a methyl group.

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Author notes

  1. S. Franklin

    Present address: Department of Physics, Bishop Heber College, Tiruchirappalli, 620017, Tamilnadu, India

Authors and Affiliations

  1. Department of Physics, National Institute of Technology, Tiruchirappalli, 620015, Tamilnadu, India

    S. Franklin & T. Balasubramanian

  2. Department of Chemistry, National Institute of Technology, Tiruchirappalli, India

    D. Tamilvendan & G. Venkatesa Prabhu

Authors
  1. S. Franklin
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  2. D. Tamilvendan
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  3. G. Venkatesa Prabhu
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  4. T. Balasubramanian
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Correspondence to T. Balasubramanian.

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Franklin, S., Tamilvendan, D., Venkatesa Prabhu, G. et al. Crystal Structure, Conformation and Vibrational Analysis of a Mannich Base: 2-[(phenylamino) methyl]-isoindole-1,3-dione. J Chem Crystallogr 41, 1120–1123 (2011). https://doi.org/10.1007/s10870-011-0055-1

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