7,11-Bis(4-methyl­phen­yl)-2,4,8,10-tetra­azaspiro­[5.5]undecane-1,3,5,9-tetra­one

Astaraki, A.M.; Bazgir, A.; Faraji, F.

doi:10.1107/S1600536808022113

Volume 64
Part 8
Page o1555
August 2008

Received 11 July 2008
Accepted 15 July 2008
Online 19 July 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.081
wR = 0.148
Data-to-parameter ratio = 16.0
Details

7,11-Bis(4-methylphenyl)-2,4,8,10-tetraazaspiro[5.5]undecane-1,3,5,9-tetraone

Ali Mohammad Astaraki,^a Ayoob Bazgir ^a ^* and Fereshteh Faraji ^b

^aDepartment of Chemistry, Islamic Azad University, Dorood Branch, Dorood 688173551, Iran, and ^bDepartment of Chemistry, Faculty of Science, Karaj Branch, Karaj, Iran
Correspondence e-mail: a_bazgir@yahoo.com

In the molecule of the title compound, C₂₁H₂₀N₄O₄, the two methylphenyl rings are oriented at a dihedral angle of 59.32 (4)°. The other two rings have flattened-boat conformations. In the crystal structure, intermolecular N-HO hydrogen bonds link the molecules. There are C-H [pi] contacts between a methylphenyl ring and methyl and methine groups.

Related literature

For general background, see: Pradhan et al. (2006); Useglio et al. (2006); Kazmierski et al. (2006). For bond-length data, see: Allen et al. (1987). For ring conformation puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₁H₂₀N₄O₄
M_r = 392.41
Monoclinic, P 2₁ /n
a = 8.852 (2) Å
b = 12.538 (3) Å
c = 17.259 (4) Å
= 104.483 (18)°
V = 1854.6 (8) Å³
Z = 4
Mo K radiation
= 0.1 mm^-1
T = 298 (2) K
0.15 × 0.11 × 0.1 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 2005) T_min = 0.979, T_max = 0.991
17766 measured reflections
4456 independent reflections
3107 reflections with I > 2(I)
R_int = 0.093

Refinement

R[F² > 2(F²)] = 0.081
wR(F²) = 0.148
S = 1.13
4456 reflections
278 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.43 e Å^-3
_min = -0.44 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C11-C14/C16/C17 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1BO2ⁱ	0.80 (5)	2.39 (5)	3.004 (3)	135 (4)
N2-H2BO3ⁱⁱ	0.77 (4)	2.32 (3)	3.065 (4)	164 (3)
N3-H3O1ⁱ	0.82 (4)	2.54 (4)	3.181 (3)	136 (3)
N4-H4DO1ⁱⁱⁱ	0.87 (4)	1.92 (4)	2.785 (3)	174 (3)
C4-H4BCg4^iv	0.96	3.02	3.721 (3)	131
C10-H10Cg4^v	0.98	3.11	3.914 (3)	141
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}]$ , $[z-{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x+1, -y+1, -z.

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2496 ).

Acknowledgements

The authors are grateful to the Islamic Azad University, Dorood Branch, 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.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Kazmierski, W. M., Furfine, E., Spaltenstein, A. & Wright, L. L. (2006). Bioorg. Med. Chem. Lett. 16, 5226-5230.
Pradhan, R., Patra, M., Behera, A. K., Mishra, B. K. & Behera, R. K. (2006). Tetrahedron, 62, 779-828.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2005). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.
Useglio, M., Castellano, P. M., Operto, M. A., Torres, R. & Kaufmen, T. S. (2006). Bioorg. Med. Chem. Lett. 16, 5097-5101.

organic compounds