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Volume 69 
Part 5 
Page o633  
May 2013  

Received 12 January 2013
Accepted 17 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.004 Å
R = 0.070
wR = 0.156
Data-to-parameter ratio = 15.4
Details
Open access

N-(2-Methyl-3-oxo-1,3-diphenylpropyl)acetamide

aSchool of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, People's Republic of China
Correspondence e-mail: jrli@bit.edu.cn

In the title compound, C18H19NO2, the dihedral angle between the benzene rings is 42.0 (1)°. In the crystal, molecules are linked by N-H...O and C-H...[pi] interactions.

Related literature

For the biological properties of N-(2-methyl-3-oxo-1,3-diphenylpropyl)acetamide derivatives, see: Barluenga et al. (1993[Barluenga, J., Viado, A., Aguilar, E., Fustero, S. & Olano, B. (1993). J. Org. Chem. 58, 5972-5975.]); Casimir et al. (1995[Casimir, J. R., Turetta, C., Ettouati, L. & Pairs, J. (1995). Tetrahedron Lett. 36, 4797-4800.]) and for their synthesis, see: Dakin & West (1928[Dakin, H. D. & West, R. (1928). J. Biol. Chem. 78, 745-756.]); Selvam & Perumal (2009[Selvam, P. & Perumal, P. (2009). Arkivoc, x, 265-282.]); Heravi et al. (2009[Heravi, M. M., Behbahani, F. K., Daraie, M. & Oskooie, H. A. (2009). Mol. Divers. 13, 375-378.]).

[Scheme 1]

Experimental

Crystal data
  • C18H19NO2

  • Mr = 281.34

  • Monoclinic, P 21 /c

  • a = 9.156 (5) Å

  • b = 17.668 (8) Å

  • c = 10.103 (5) Å

  • [beta] = 107.914 (7)°

  • V = 1555.0 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 153 K

  • 0.61 × 0.07 × 0.02 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.954, Tmax = 0.998

  • 12600 measured reflections

  • 3028 independent reflections

  • 2386 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.070

  • wR(F2) = 0.156

  • S = 1.00

  • 3028 reflections

  • 197 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C10-C15 and C1-C6 benzene rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2i 0.94 (3) 1.98 (3) 2.874 (3) 158 (2)
C1-H1...Cg1i 0.95 2.85 (1) 3.649 (3) 142 (1)
C16-H16A...Cg2ii 0.98 2.98 (1) 3.472 (3) 112 (1)
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) [-x+1, y+{\script{3\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku/MSC, 2009[Rigaku/MSC (2009). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); software used to prepare material for publication: CrystalStructure.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2279 ).


Acknowledgements

The authors thank Beijing Institute of Technology for the X-ray diffraction analysis.

References

Barluenga, J., Viado, A., Aguilar, E., Fustero, S. & Olano, B. (1993). J. Org. Chem. 58, 5972-5975.  [CrossRef] [ChemPort]
Casimir, J. R., Turetta, C., Ettouati, L. & Pairs, J. (1995). Tetrahedron Lett. 36, 4797-4800.  [ChemPort]
Dakin, H. D. & West, R. (1928). J. Biol. Chem. 78, 745-756.  [ChemPort]
Heravi, M. M., Behbahani, F. K., Daraie, M. & Oskooie, H. A. (2009). Mol. Divers. 13, 375-378.  [ISI] [CrossRef] [PubMed] [ChemPort]
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2009). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Selvam, P. & Perumal, P. (2009). Arkivoc, x, 265-282.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o633  [ doi:10.1107/S1600536813007320 ]

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