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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 [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.046
wR = 0.104
Data-to-parameter ratio = 6.6
Details
Open access

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

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-H...O hydrogen bonds.

Related literature

For the synthesis, see: Hu et al. (2006[Hu, Y.-G., Zheng, A.-H. & Li, G.-H. (2006). Acta Cryst. E62, o1457-o1459.], 2007[Hu, Y.-G., Hu, J. & Gao, H.-T. (2007). Acta Cryst. E63, o4735.], 2010[Hu, Y. G., Wang, Y., Du, S. M., Chen, X. B. & Ding, M. W. (2010). Bioorg. Med. Chem. Lett. 20, 6188-6190.]). For related structures, see: He et al. (2007a[He, P., Peng, X.-M. & Li, G.-H. (2007a). Acta Cryst. E63, o4884.],b[He, P., Zheng, A., Cai, C.-Q. & Fang, C.-L. (2007b). Acta Cryst. E63, o3185.]); Ma et al. (2009[Ma, J.-K., He, M. & Hu, Y.-G. (2009). Acta Cryst. E65, o2629.]); Zeng & Yan (2008[Zeng, G.-P. & Yan, S.-R. (2008). Acta Cryst. E64, o1680.]).

[Scheme 1]

Experimental

Crystal data
  • C25H26N4O3

  • Mr = 430.50

  • Monoclinic, C c

  • a = 19.481 (2) Å

  • b = 12.0745 (13) Å

  • c = 10.4393 (11) Å

  • [beta] = 115.006 (2)°

  • V = 2225.4 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.991

  • 7050 measured reflections

  • 2192 independent reflections

  • 1846 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.104

  • S = 1.00

  • 2192 reflections

  • 332 parameters

  • 12 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O1i 0.93 2.50 3.320 (5) 147
C19-H19B...O1ii 0.96 2.59 3.545 (8) 175
C25-H25...O2iii 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[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, 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: PLATON (Spek, 2009)[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]; software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


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.  [CSD] [CrossRef] [details]
He, P., Zheng, A., Cai, C.-Q. & Fang, C.-L. (2007b). Acta Cryst. E63, o3185.  [CSD] [CrossRef] [details]
Hu, Y.-G., Hu, J. & Gao, H.-T. (2007). Acta Cryst. E63, o4735.  [CSD] [CrossRef] [details]
Hu, Y. G., Wang, Y., Du, S. M., Chen, X. B. & Ding, M. W. (2010). Bioorg. Med. Chem. Lett. 20, 6188-6190.  [CSD] [CrossRef] [ChemPort] [PubMed]
Hu, Y.-G., Zheng, A.-H. & Li, G.-H. (2006). Acta Cryst. E62, o1457-o1459.  [CSD] [CrossRef] [details]
Ma, J.-K., He, M. & Hu, Y.-G. (2009). Acta Cryst. E65, o2629.  [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]
Zeng, G.-P. & Yan, S.-R. (2008). Acta Cryst. E64, o1680.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o118  [ doi:10.1107/S1600536811052883 ]

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