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Volume 69 
Part 10 
Page o1513  
October 2013  

Received 7 August 2013
Accepted 21 August 2013
Online 7 September 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.131
Data-to-parameter ratio = 18.6
Details
Open access

(6,6-Dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-2-yl)(thiophen-2-yl)methanone

aCollege of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuan 050016, People's Republic of China,bShanghai Institute of Pharmaceutical Industry, Shanghai 200040, People's Republic of China, and cBeijing Chao-Yang Hospital Affiliated with Beijing Capital Medical University, Beijing 100020, People's Republic of China
Correspondence e-mail: liuheliuhe@126.com

In the title compound, C20H19NOS, the pyrrolizine ring is essentially planar (r.m.s. deviation = 0.001 Å) while the fused dihydro-pyrrolizine ring adopts an envelope comformation with the C atom bearing the methyl substituents as the flap. The dihedral angles between the pyrrolizine and the phenyl and thiophene rings are 34.54 (7) and 44.93 (7)°, respectively. In the crystal, weak C-H...O hydrogen bonds link the molecules into infinite zigzag chains parallel to the b-axis direction.

Related literature

For the synthesis of the title compound, see: Dannhardt & Obergrusberger (1979[Dannhardt, G. & Obergrusberger, R. (1979). Arch. Pharm. 312, 896-907.]). For a similar structure, see: Liu et al. (2007[Liu, Y., Hu, Y., Li, X. & Chen, W. (2007). Acta Cryst. E63, o1106-o1107.]).

[Scheme 1]

Experimental

Crystal data
  • C20H19NOS

  • Mr = 321.42

  • Orthorhombic, P b c a

  • a = 16.251 (3) Å

  • b = 10.473 (2) Å

  • c = 19.973 (4) Å

  • V = 3399.3 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 296 K

  • 0.22 × 0.19 × 0.12 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 30107 measured reflections

  • 3894 independent reflections

  • 2743 reflections with I > 2[sigma](I)

  • Rint = 0.070

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.131

  • S = 1.03

  • 3894 reflections

  • 209 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C13-H13A...O1i 0.93 2.69 3.529 (3) 150
Symmetry code: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2493 ).


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.
Dannhardt, G. & Obergrusberger, R. (1979). Arch. Pharm. 312, 896-907.  [CrossRef] [ChemPort]
Liu, Y., Hu, Y., Li, X. & Chen, W. (2007). Acta Cryst. E63, o1106-o1107.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1513  [ doi:10.1107/S1600536813023489 ]

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