Methyl 6-(4-chloro­phen­yl)-2,4-dimethyl-1,3-dioxo-1,2,3,4,6,6a,7,12b-octa­hydro­chromeno[4′,3′:4,5]pyrano[2,3-d]pyrimidine-6a-carboxyl­ate

Kanchanadevi, J.; Anbalagan, G.; Sivakumar, G.; Bakthadoss, M.; Manivannan, V.

doi:10.1107/S160053681102678X

Volume 67
Part 8
Page o1990
August 2011

Received 23 June 2011
Accepted 5 July 2011
Online 9 July 2011

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.002 Å
R = 0.052
wR = 0.158
Data-to-parameter ratio = 24.0
Details

Methyl 6-(4-chlorophenyl)-2,4-dimethyl-1,3-dioxo-1,2,3,4,6,6a,7,12b-octahydrochromeno[4',3':4,5]pyrano[2,3-d]pyrimidine-6a-carboxylate

J. Kanchanadevi,^a G. Anbalagan,^b G. Sivakumar,^c M. Bakthadoss ^c and V. Manivannan ^d ^*

^aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India,^bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India,^cDepartment of Organic Chemistry, University of Madras, Maraimalai campus, Chennai 600 025, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
Correspondence e-mail: crystallography2010@gmail.com, phdguna@gmail.com

In the title compound, C₂₄H₂₁ClN₂O₆, the two fused six-membered pyran rings adopt half-chair conformations. The dihedral angle between the pyrimidine ring and the chlorophenyl ring is 51.55 (3)°. In the crystal, molecules are linked by pairs of weak intermolecular C-HO hydrogen bonds, forming inversion dimers. A C-H [pi] interaction is also observed.

Related literature

For biological activity of pyrimidine derivatives, see: Alam et al. (2005); Kappe (2000); Condon et al. (1993); Rovnyak et al. (1995); Leite et al. (2006); Sriram et al. (2006). For related structures, see: Booysen et al. (2011); Noroozi Pesyan et al. (2009).

Experimental

Crystal data

C₂₄H₂₁ClN₂O₆
M_r = 468.88
Monoclinic, P 2₁ /c
a = 10.6177 (5) Å
b = 11.9973 (5) Å
c = 17.5532 (8) Å
= 99.751 (2)°
V = 2203.69 (17) Å³
Z = 4
Mo K radiation
= 0.22 mm^-1
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.924, T_max = 0.951
29343 measured reflections
7232 independent reflections
4518 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.052
wR(F²) = 0.158
S = 1.03
7232 reflections
301 parameters
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.60 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C1-C5/C9 ring.

D-HA	D-H	HA	DA	D-HA
C16-H16O3ⁱ	0.93	2.44	3.349 (2)	166
C19-H19Cg4ⁱⁱ	0.93	2.84	3.720 (3)	158
Symmetry codes: (i) -x+1, -y, -z; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2742 ).

References

Alam, O., Imran, M. & Khan, S. A. (2005). Indian J. Heterocycl. Chem. 14, 293-296.
Booysen, I., Muhammed, I., Soares, A., Gerber, T., Hosten, E. & Betz, R. (2011). Acta Cryst. E67, o1592.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Condon, M. E., Brady, T. E., Feist, D., Malefyt, T., Marc, P., Quakenbush, L. S., Rodaway, S. J., Shaner, D. L. & Tecle, B. (1993). Brighton Crop Protection Conference-Weeds, pp. 41-46.
Kappe, C. O. (2000). Acc. Chem. Res. 33, 879-888.
Leite, A. C. L., Lima, R. S., Moreira, D. R. M., Cardoso, M. V. O., Brito, A. C. G., Santos, L. M. F., Hernandes, M. Z., Kiperstok, A. C., Lima, R. S. & Soares, M. B. P. (2006). Bioorg. Med. Chem. 14, 3749-3757.
Noroozi Pesyan, N., Rastgar, S. & Hosseini, Y. (2009). Acta Cryst. E65, o1444.
Rovnyak, G. C., Kimball, S. D., Beyer, B., Cucinotta, G., DiMarco, J. D., Gougoutas, J., Hedberg, A., Malley, M., McCarthy, J. P., Zhang, R. & Moreland, S. (1995). J. Med. Chem. 38, 119-129.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sriram, D., Yogeeswari, P. & Devakaram, R. V. (2006). Bioorg. Med. Chem. 14, 3113-3118.

organic compounds