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

Inglebert, S.A.; Sethusankar, K.; Arun, Y.; Perumal, P.T.

doi:10.1107/S1600536811051786

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 (C-C) = 0.007 Å
R = 0.049
wR = 0.148
Data-to-parameter ratio = 11.8
Details

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

S. Antony Inglebert,^a K. Sethusankar,^b ^* Yuvaraj Arun ^c and Paramasivam T. Perumal ^c

^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-HO contact, which generates an S(6) ring motif. The crystal packing are stabilized by C-HO interactions.

Related literature

For a related structure, see: Inglebert et al. (2011). For general background and applications of coumarin derivatives, see: Griffiths et al. (1995); Yu et al. (2006). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₆H₃₃NO₇
M_r = 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 radiation
= 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) T_min = 0.974, T_max = 0.983
10574 measured reflections
3699 independent reflections
2668 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.148
S = 1.09
3699 reflections
314 parameters
1 restraint
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O6	0.86	1.99	2.659 (4)	135
C2-H2O6ⁱ	0.93	2.47	3.252 (5)	141
C4-H4O4ⁱⁱ	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Griffiths, J., Millar, V. & Bahra, G. S. (1995). Dyes Pigm. 28, 327-339.
Inglebert, S. A., Sethusankar, K., Arun, Y. & Perumal, P. T. (2011). Acta Cryst. E67, o2955.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yu, T.-Z., Zhao, Y.-L. & Fan, D.-W. (2006). J. Mol. Struct. 791, 18-22.

organic compounds