2-Amino-5,7-bis­(4-fluoro­phen­yl)-1′,3′-dimethyl-7,8-dihydro­spiro­[pyrido[2,3-d]pyrimidine-6(5H),5′-pyrimidine]-2′,4,4′,6′(3H,1′H,3′H,5′H)-tetra­one ethanol solvate

Zhu, X.-T.; Zhang, G.; Ma, N.

doi:10.1107/S1600536809022946

Volume 65
Part 7
Page o1625
July 2009

Received 6 June 2009
Accepted 15 June 2009
Online 20 June 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R = 0.066
wR = 0.120
Data-to-parameter ratio = 13.6
Details

2-Amino-5,7-bis(4-fluorophenyl)-1',3'-dimethyl-7,8-dihydrospiro[pyrido[2,3-d]pyrimidine-6(5H),5'-pyrimidine]-2',4,4',6'(3H,1'H,3'H,5'H)-tetraone ethanol solvate

Xiao-Tong Zhu,^a ^* Ge Zhang ^b and Ning Ma ^b

^aDepartment of Chemistry, Xuzhou Medical College, Jiangsu 221004, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
Correspondence e-mail: laotu2001@263.net

In the molecule of the title compound, C₂₄H₂₀F₂N₆O₄·C₂H₅OH, the pyrimidine ring is oriented at dihedral angles of 42.64 (3) and 62.94 (3)° with respect to the benzene rings, while the dihedral angle between the benzene rings is 74.45 (3)°. The pyridine ring adopts an envelope conformation. In the crystal structure, intermolecular N-HO and O-HN hydrogen bonds link the molecules into a two-dimensional network, forming R₂²(8) ring motifs. [pi] - [pi] contacts between the pyrimidine and benzene rings [centroid-centroid distances = 3.516 (1) and 3.927 (1) Å] may further stabilize the structure.

Related literature

For bond-length data, see: Allen et al. (1987). For ring-motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₄H₂₀F₂N₆O₄·C₂H₆O
M_r = 540.53
Triclinic, $[P \overline 1]$
a = 9.2189 (15) Å
b = 12.5924 (17) Å
c = 14.100 (2) Å
= 64.634 (2)°
= 81.467 (3)°
= 69.027 (2)°
V = 1381.0 (4) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 298 K
0.40 × 0.37 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.961, T_max = 0.988
7223 measured reflections
4773 independent reflections
1979 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.120
S = 1.00
4773 reflections
352 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3O1ⁱ	0.86	1.88	2.737 (3)	177
N4-H4AO5ⁱⁱ	0.86	2.07	2.890 (3)	160
O5-H5N2ⁱⁱⁱ	0.82	2.19	2.779 (3)	129
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+1, -y+2, -z; (iii) x+1, y, z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2707 ).

Acknowledgements

The authors are grateful to the Foundation of Xuzhou Medical College (grant No. 08 K J06) for financial support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
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.

organic compounds