3,3,5,5-Tetra­methyl-r-2,c-6-diphenyl­piperidin-4-one

Govindaraju, C.; Valliappan, R.; Sundari, V.

doi:10.1107/S1600536812018983

Volume 68
Part 7
Page o2097
July 2012

Received 28 March 2012
Accepted 27 April 2012
Online 13 June 2012

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
R = 0.056
wR = 0.152
Data-to-parameter ratio = 12.3
Details

3,3,5,5-Tetramethyl-r-2,c-6-diphenylpiperidin-4-one

C. Govindaraju,^a ^* R. Valliappan ^a and V. Sundari ^a

^aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India
Correspondence e-mail: chitragovi12@gmail.com

The piperidone ring of the title compound, C₂₁H₂₅NO, adopts a chair conformation with the two phenyl groups equatorially oriented and cis to each other. In the crystal, molecules are linked by weak N-HO hydrogen bonds, forming chains parallel to [100].

Related literature

For some bioactive properties of piperidones, see: Mobio et al. (1989). For piperidone ring conformations in related compounds, see: Parthiban et al. (2008); Lakshminarayana et al. (2009); Ravichandran et al. (2010). For the synthesis, see: Noller & Baliah (1948). For ring puckering parameters, see: Nardelli (1983); Cremer & Pople (1975).

Experimental

Crystal data

C₂₁H₂₅NO
M_r = 307.42
Triclinic, $[P \overline 1]$
a = 6.9227 (11) Å
b = 11.540 (2) Å
c = 12.472 (2) Å
= 64.771 (4)°
= 80.755 (5)°
= 72.675 (4)°
V = 859.8 (3) Å³
Z = 2
Mo K radiation
= 0.07 mm^-1
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.919, T_max = 0.986
12752 measured reflections
2659 independent reflections
2123 reflections with I > 2(I)
R_int = 0.032
_max = 24.0°

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.152
S = 1.15
2659 reflections
217 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1ⁱ	0.94 (3)	2.39 (3)	3.258 (3)	153 (2)
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2058 ).

Acknowledgements

The authors thank the SAIF, IIT Madras, for the X- ray data collection.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Bruker (2004). APEX2 and SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Lakshminarayana, B. N., Shashidhara Prasad, J., Gnanendra, C. R., Sridhar, M. A. & Naik, N. (2009). Acta Cryst. E65, o1001.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Mobio, I. G., Soldatenkov, A. T., Federov, V. O., Ageev, E. A., Sergeeva, N. D., Lin, S., Stashenko, E. E., Prostakov, N. S. & Andreeva, E. I. (1989). Khim. Farm. Zh. 23, 421-427.
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.
Noller, C. R. & Baliah, V. (1948). J. Am. Chem. Soc. 70, 3853-3855.
Parthiban, P., Ramkumar, V., Kumar, N. A., Kim, J. S. & Jeong, Y. T. (2008). Acta Cryst. E64, o1631.
Ravichandran, K., Ramesh, P., Jeganathan, P., Ponnuswamy, S. & Ponnuswamy, M. N. (2010). Acta Cryst. E66, o276-o277.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds