[Journal logo]

Volume 68 
Part 1 
Page o112  
January 2012  

Received 22 October 2011
Accepted 1 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.007 Å
R = 0.049
wR = 0.148
Data-to-parameter ratio = 11.8
Details
Open access

rac-Diethyl 5-oxo-2-[(2,4,4-trimethylpentan-2-yl)amino]-4,5-dihydropyrano[3,2-c]chromene-3,4-dicarboxylate

aDepartment of Physics, Sri Ram Engineering College, Chennai 602 024, India,bDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and cOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India
Correspondence e-mail: ksethusankar@yahoo.co.in

The title compound, C26H33NO7, comprises a racemic mixture of asymmetric molecules containing one stereogenic centre. The dihedral angle between the mean planes of the fused pyran ring and the coumarin ring system is 8.12 (14)°. The molecular structure features a short N-H...O contact, which generates an S(6) ring motif. The crystal packing are stabilized by C-H...O interactions.

Related literature

For a related structure, see: Inglebert et al. (2011[Inglebert, S. A., Sethusankar, K., Arun, Y. & Perumal, P. T. (2011). Acta Cryst. E67, o2955.]). For general background and applications of coumarin derivatives, see: Griffiths et al. (1995[Griffiths, J., Millar, V. & Bahra, G. S. (1995). Dyes Pigm. 28, 327-339.]); Yu et al. (2006[Yu, T.-Z., Zhao, Y.-L. & Fan, D.-W. (2006). J. Mol. Struct. 791, 18-22.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C26H33NO7

  • Mr = 471.53

  • Orthorhombic, P n a 21

  • a = 11.6910 (17) Å

  • b = 18.786 (3) Å

  • c = 11.7305 (15) Å

  • V = 2576.3 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 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, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.974, Tmax = 0.983

  • 10574 measured reflections

  • 3699 independent reflections

  • 2668 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.148

  • S = 1.09

  • 3699 reflections

  • 314 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 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
N1-H1...O6 0.86 1.99 2.659 (4) 135
C2-H2...O6i 0.93 2.47 3.252 (5) 141
C4-H4...O4ii 0.93 2.43 3.306 (5) 157
Symmetry codes: (i) x, y, z-1; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); 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: RK2310 ).


Acknowledgements

The authors gratefully acknowledge Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection and Dr V. Murugan, Head of the Physics Department, RKM Vivekananda College, Chennai, India, for providing facilities in the department to carry out this work.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Griffiths, J., Millar, V. & Bahra, G. S. (1995). Dyes Pigm. 28, 327-339.  [CrossRef] [ChemPort]
Inglebert, S. A., Sethusankar, K., Arun, Y. & Perumal, P. T. (2011). Acta Cryst. E67, o2955.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yu, T.-Z., Zhao, Y.-L. & Fan, D.-W. (2006). J. Mol. Struct. 791, 18-22.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o112  [ doi:10.1107/S1600536811051786 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.