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

Ali Mohammad Astaraki; Ayoob Bazgir; Fereshteh Faraji

doi:10.1107/S1600536808022113

. 2008 Jul 19;64(Pt 8):o1555. doi: 10.1107/S1600536808022113

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,^*, Fereshteh Faraji ^b

PMCID: PMC2961972 PMID: 21203258

Abstract

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—H⋯O hydrogen bonds link the molecules. There are C—H⋯π 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,
a = 8.852 (2) Å
b = 12.538 (3) Å
c = 17.259 (4) Å
β = 104.483 (18)°
V = 1854.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.093

Refinement

R[F ² > 2σ(F ²)] = 0.081
wR(F ²) = 0.148
S = 1.13
4456 reflections
278 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.44 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022113/hk2496sup1.cif

e-64-o1555-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022113/hk2496Isup2.hkl

e-64-o1555-Isup2.hkl^{(213.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2ⁱ	0.80 (5)	2.39 (5)	3.004 (3)	135 (4)
N2—H2B⋯O3ⁱⁱ	0.77 (4)	2.32 (3)	3.065 (4)	164 (3)
N3—H3⋯O1ⁱ	0.82 (4)	2.54 (4)	3.181 (3)	136 (3)
N4—H4D⋯O1ⁱⁱⁱ	0.87 (4)	1.92 (4)	2.785 (3)	174 (3)
C4—H4B⋯Cg4^iv	0.96	3.02	3.721 (3)	131
C10—H10⋯Cg4^v	0.98	3.11	3.914 (3)	141

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) , ; (iv) ; (v) .

Acknowledgments

The authors are grateful to the Islamic Azad University, Dorood Branch, for financial support.

supplementary crystallographic information

Comment

Spiro compounds having cyclic structures fused at a central carbon are of recent interest, due to their interesting conformational feature and structural implications on biological systems (Pradhan et al., 2006). The asymmetric characteristic of the molecule due to the chiral spiro carbon is one of the important criteria of the biological activities. For example, some spiro compounds show antibacterial and antiviral activities (Useglio et al., 2006, Kazmierski et al., 2006). We report herein the synthesis and crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C1-C3/C5-C7) and C (C11-C14/C16/C17) are, of course, planar and they are oriented at a dihedral angle of A/C = 59.32 (4)°. Rings B (N1/N2/C8-C10/C18) and D (N3/N4/C18-C21) have flattened-boat [φ = -54.22 (2)°, θ = 129.53 (3)° (for ring B) and φ = 52.72 (3)°, θ = 21.44 (3)° (for ring D)] conformations, having total puckering amplitudes, Q_T, of 1.186 (3) and 0.174 (3) Å, respectively (Cremer & Pople, 1975).

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. The C—H···π contacts (Table 1) between the ring C and the methyl and methine groups further stabilize the structure.

Experimental

For the preparation of the title compound, a mixture of 4-methylbenzaldehyde (0.24 g, 2 mmol), barbituric acid (0.13 g, 1 mmol), and urea (0.06 g, 1 mmol) was heated at 373 K. After 2 h, the reaction mixture was washed with water (10 ml). The residue recrystallized from ethanol to afford the pure product (yield; 0.25 g, 65%, m.p. 519-521 K).