t-3-Benzyl-r-2,c-6-diphenylpiperidin-4-one

R. Arulraj, S. Sivakumar, A. Thiruvalluvar, A. Manimekalai
  • IUCrData, February 2016, International Union of Crystallography
  • DOI: 10.1107/s2414314616001887

t -3-Benzyl- r -2, c -6-diphenylpiperidin-4-one

What is it about?

The asymmetric unit of the title compound, C24H23NO, contains two crystallographically independent molecules (A and B). In both molecules, the piperidine rings adopt a chair conformation and the phenyl rings and the benzyl group substituents are attached equatorially. The dihedral angle between the phenyl rings is 60.80 (10) in molecule A and 68.43 (9) in molecule B. The phenyl ring of the benzyl group makes dihedral angles of 76.95 (9) and 42.25 (10) with the phenyl rings in molecule A, and dihedral angles of 81.38 (11) and 30.19 (11) in molecule B. In the crystal, the two molecules are linked by N—H  O hydrogen bonds, forming –A–B–A–B– chains along [100]. In addition, five C—H   interactions are also present, linking the chains to form a three-dimensional structure.

Why is it important?

The asymmetric unit of the title compound, (Fig. 1 and Fig. 2), contains two crystallographically independent molecules (A and B). In both molecules, the piperidine ring adopts a chair conformation with puckering parameters q2 = 0.0236 (18) A ° , q3 = 0.5892 (18) A ° , Q = 0.5895 (18) A ° ,  = 178.12 (17) and ’ = 141 (4) for molecule A and q2 = 0.0396 (18) A ° , q3 = 0.5886 (18) A ° , Q = 0.5898 (18) A ° ,  = 176.34 (17) and ’ = 133 (3) for molecule B. An AutoMolFit of molecule A on molecule B gives the best fit (Fig. 3; Spek, 2009). Weighted and unit weight r.m.s. fit are 0.248 and 0.219 A ° , respectively (for all 26 non-H atoms). Comparison of the bonds of the fitted residues gives, r.m.s. bond fit = 0.0033 A ° . Comparison of the bond angles of the fitted residues gives r.m.s. angle fit = 0.683. The phenyl rings at positions 2,6 and the benzyl group at position 3 are attached equatorially. The dihedral angle between the two phenyl rings at positions 2 and 6 is 60.80 (10) in molecule A, and 68.43 (9) in molecule B. The phenyl ring of the benzyl group makes dihedral angles of 76.95 (9) and 42.25 (10) with the two phenyl rings in molecule A, and 81.38 (11) and 30.19 (11) in molecule B. In the crystal, the molecules are linked by N—H  O hydrogen bonds forming –A–B–A–B– chains along the a-axis direction (Fig. 4). In addition, there are a number of C—H   interactions present, linking the chains to form a threedimensional structure

Perspectives

Dr Sivakumar S
Thiruvalluvar Arts and Science College, Kurinjipadi

R. Arulraj,a S. Sivakumar,a,b* A. Thiruvalluvarc and A. Manimekalaid aResearch and Development Centre, Bharathiar University, Coimbatore 641 046, Tamilnadu, India, bDepartment of Chemistry, Thiruvalluvar Arts and Science College, Kurinjipadi 607 302, Tamilnadu, India, cPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, and dDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India. *Correspondence e-mail: sivakumar.phd2015@gmail.com

Dr Thiruvalluvar Aravazhiamalan
Rajah Serfoji Government College (Autonomous), Thanjavur - 613 005, Tamilnadu

This publication is our first publication in IUCrData.

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http://dx.doi.org/10.1107/s2414314616001887

The following have contributed to this page: Dr Sivakumar S, Dr Arulraj Ramalingam, Dr Thiruvalluvar Aravazhiamalan, and Dr Thiruvalluvar Aravazhiamalan