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Volume 69 
Part 5 
Page o776  
May 2013  

Received 16 April 2013
Accepted 17 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 292 K
Mean [sigma](C-C) = 0.005 Å
R = 0.092
wR = 0.182
Data-to-parameter ratio = 13.8
Details
Open access

Methyl 9-(4-methoxyphenyl)-19-methyl-3,12-diazapentacyclo[10.7.0.02,10.03,8.013,18]nonadeca-1(19),13(18),14,16-tetraene-10-carboxylate

aDepartment of Physics, Kalasalingam University, Krishnankoil 626 126, India,bLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India, and cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: s_selvanayagam@rediffmail.com

The title ester, C27H30N2O3, crystallizes with two independent molecules in the asymmetric unit whose geometrical features are similar. In each molecule, the pyrrolidine ring adopts an envelope conformation, with the fused C atom shared with the piperidine ring as the flap, and the piperidine ring adopts a chair conformation. In the crystal, C-H...[pi] interactions link the inversion-related molecules and form a dimeric arrangement in the unit cell.

Related literature

For the superposition of molecules using Qmol, see: Gans & Shalloway (2001[Gans, J. D. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.]). For ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C27H30N2O3

  • Mr = 430.53

  • Monoclinic, P 21 /n

  • a = 22.672 (3) Å

  • b = 8.8049 (11) Å

  • c = 24.431 (3) Å

  • [beta] = 110.487 (2)°

  • V = 4568.6 (10) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 292 K

  • 0.22 × 0.20 × 0.18 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • 42435 measured reflections

  • 8045 independent reflections

  • 5762 reflections with I > 2[sigma](I)

  • Rint = 0.069

Refinement
  • R[F2 > 2[sigma](F2)] = 0.092

  • wR(F2) = 0.182

  • S = 1.18

  • 8045 reflections

  • 583 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C19A-C24A and C19B-C24B rings, respectively.

D-H...A D-H H...A D...A D-H...A
C25A-H25A...Cg1i 0.96 2.81 3.606 (5) 141
C25B-H25F...Cg2ii 0.96 2.68 3.495 (5) 143
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+2, -y+1, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97 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: NG5324 ).


Acknowledgements

SS acknowledges the Department of Science and Technology (DST), India, for providing computing facilities under the DST-Fast Track Scheme. SS also thanks the Vice Chancellor and Management of the Kalasalingam University, Krishnankoil, for their support and encouragement.

References

Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gans, J. D. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o776  [ doi:10.1107/S1600536813010489 ]

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