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Volume 69 
Part 12 
Page o1730  
December 2013  

Received 8 October 2013
Accepted 25 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.005 Å
R = 0.062
wR = 0.194
Data-to-parameter ratio = 13.8
Details
Open access

Ethyl 2-[6-(4-methyl­benzo­yl)-7-phenyl-2,3-di­hydro-1H-pyrrolizin-5-yl]-2-oxo­acetate

aShanghai Institute of Pharmaceutical Industry, Shanghai 200040, China, and bBeijing Chao-Yang Hospital Affiliated with Beijing Capital, Medical University, Beijing 100020, China
Correspondence e-mail: liuheliuhe@126.com

In the title compound, C25H23NO4, the pyrrolizine ring is approximately planar with an r.m.s deviation from planarity of 0.0053 Å, while the fused di­hydro­pyrrolizine ring adopts an envelope conformation with the C atom connected to two CH2 as the flap. The dihedral angles between the fused ring system and the phenyl and methyl­benzoyl rings are 41.65 (11) and 66.30 (8)°, respectively. In the crystal, weak C-H...O hydrogen bonds and C-H...[pi] inter­actions occur. One mol­ecule is linked to five adjacent ones through eight hydrogen bonds, forming a three-dimensional network.

Related literature

For the synthesis of the title compound, see: Itoh et al. (1984[Itoh, O., Nagata, T., Nomura, I., Takanaga, T., Sugita, T. & Ichikawa, K. (1984). Bull. Chem. Soc. Jpn, 57, 810-814.]). For similar structures, see: Liu et al. (2007[Liu, Y., Hu, Y., Li, X. & Chen, W. (2007). Acta Cryst. E63, o1106-o1107.], 2013[Liu, Y., Zhong, J., Sun, W., Zhang, F. & Liu, H. (2013). Acta Cryst. E69, o1513.]).

[Scheme 1]

Experimental

Crystal data
  • C25H23NO4

  • Mr = 401.44

  • Monoclinic, P 21 /c

  • a = 8.8949 (18) Å

  • b = 9.0003 (18) Å

  • c = 25.580 (5) Å

  • [beta] = 96.75 (3)°

  • V = 2033.7 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.26 × 0.15 × 0.10 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 16259 measured reflections

  • 3775 independent reflections

  • 1930 reflections with I > 2[sigma](I)

  • Rint = 0.070

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.194

  • S = 0.97

  • 3775 reflections

  • 274 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C21-C26 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C20-H20B...O3i 0.96 2.64 3.268 (6) 123
C12-H12B...O2ii 0.96 2.63 3.579 (5) 170
C12-H12A...O1iii 0.96 2.66 3.376 (5) 132
C2-H2A...O4iv 0.97 2.70 3.391 (5) 128
C19-H19...Cg4v 0.93 2.96 3.769 (5) 147
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) -x+1, -y+2, -z; (v) -x, -y, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZP2010 ).


Acknowledgements

We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 81072530).

References

Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Itoh, O., Nagata, T., Nomura, I., Takanaga, T., Sugita, T. & Ichikawa, K. (1984). Bull. Chem. Soc. Jpn, 57, 810-814.  [CrossRef] [ChemPort] [Web of Science]
Liu, Y., Hu, Y., Li, X. & Chen, W. (2007). Acta Cryst. E63, o1106-o1107.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Liu, Y., Zhong, J., Sun, W., Zhang, F. & Liu, H. (2013). Acta Cryst. E69, o1513.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1730  [ doi:10.1107/S1600536813029401 ]

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