Ethyl 2-diethyl­amino-4-oxo-3,5-diphenyl-4,5-dihydro-3H-pyrrolo­[3,2-d]pyrimidine-7-carboxyl­ate

Gao, H.-T.; Li, L.; Ye, F.; Hu, Y.-G.

doi:10.1107/S1600536811052883

Volume 68
Part 1
Page o118
January 2012

Received 12 November 2011
Accepted 8 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R = 0.046
wR = 0.104
Data-to-parameter ratio = 6.6
Details

Ethyl 2-diethylamino-4-oxo-3,5-diphenyl-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidine-7-carboxylate

Hai-Tao Gao,^a Li Li,^b Fang Ye ^c ^* and Yang-Gen Hu ^c,^a ^*

^aInstitute of Medicinal Chemistry, Hubei University of Medicine, Shiyan 442000, People's Republic of China,^bThe Library of Hubei University of Medicine, Shiyan 442000, People's Republic of China, and ^cDepartment of Pharmacy, Taihe Hospital of Hubei University of Medicine, Shiyan 442000, People's Republic of China
Correspondence e-mail: , huyangg111@yahoo.com.cn

In the title compound, C₂₅H₂₆N₄O₃, the two fused pyrrolo[3,2-d]pyrimidine rings form a dihedral angle of 3.7 (2)°. The two substituent phenyl rings are twisted with respect to the pyrrole and pyrimidine rings, making dihedral angles of 57.2 (2) and 69.0 (2)°, respectively. The ethyl and ethoxy groups are disordered over two positions; the site occupancies are 0.53 (1) and 0.47 (1) for ethyl, and 0.63 (1) and 0.37 (1) for ethoxy. The crystal packing features C-HO hydrogen bonds.

Related literature

For the synthesis, see: Hu et al. (2006, 2007, 2010). For related structures, see: He et al. (2007a,b); Ma et al. (2009); Zeng & Yan (2008).

Experimental

Crystal data

C₂₅H₂₆N₄O₃
M_r = 430.50
Monoclinic, C c
a = 19.481 (2) Å
b = 12.0745 (13) Å
c = 10.4393 (11) Å
= 115.006 (2)°
V = 2225.4 (4) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 298 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002) T_min = 0.973, T_max = 0.991
7050 measured reflections
2192 independent reflections
1846 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.104
S = 1.00
2192 reflections
332 parameters
12 restraints
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O1ⁱ	0.93	2.50	3.320 (5)	147
C19-H19BO1ⁱⁱ	0.96	2.59	3.545 (8)	175
C25-H25O2ⁱⁱⁱ	0.93	2.60	3.295 (5)	132
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z-1]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2034 ).

Acknowledgements

We gratefully acknowledge financial support of this work by the Science Research Project of Hubei University of Medicine (Nos. 2008CXG01 and 2009QDJ15).

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
He, P., Peng, X.-M. & Li, G.-H. (2007a). Acta Cryst. E63, o4884.
He, P., Zheng, A., Cai, C.-Q. & Fang, C.-L. (2007b). Acta Cryst. E63, o3185.
Hu, Y.-G., Hu, J. & Gao, H.-T. (2007). Acta Cryst. E63, o4735.
Hu, Y. G., Wang, Y., Du, S. M., Chen, X. B. & Ding, M. W. (2010). Bioorg. Med. Chem. Lett. 20, 6188-6190.
Hu, Y.-G., Zheng, A.-H. & Li, G.-H. (2006). Acta Cryst. E62, o1457-o1459.
Ma, J.-K., He, M. & Hu, Y.-G. (2009). Acta Cryst. E65, o2629.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zeng, G.-P. & Yan, S.-R. (2008). Acta Cryst. E64, o1680.

organic compounds