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

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1555

doi:10.1107/S1600536808022113

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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

(Received 11 July 2008; accepted 15 July 2008; online 19 July 2008)

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, P 2₁ /n
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[F² > 2σ(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
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.44 e Å⁻³

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
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 ).

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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). Cg4 is the centroid of the C11–C14/C16/C17 ring. Please check/supply symmetry codes.

Experimental top

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).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-RED (Stoe & Cie, 2005); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₂₁H₂₀N₄O₄	F(000) = 824
M_r = 392.41	D_x = 1.405 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2021 reflections
a = 8.852 (2) Å	θ = 2.0–28.1°
b = 12.538 (3) Å	µ = 0.1 mm⁻¹
c = 17.259 (4) Å	T = 298 K
β = 104.483 (18)°	Prism, yellow
V = 1854.6 (8) Å³	0.15 × 0.11 × 0.1 mm
Z = 4

Data collection top

Stoe IPDSII diffractometer	3107 reflections with I > 2σ(I)
rotation method scans	R_int = 0.093
Absorption correction: numerical shape of crystal determined optically (X-SHAPE; Stoe & Cie, 2005))	θ_max = 28.1°, θ_min = 2.0°
T_min = 0.979, T_max = 0.991	h = −11→11
17766 measured reflections	k = −16→16
4456 independent reflections	l = −22→22

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.081	w = 1/[σ²(F_o²) + (0.0701P)² + 0.8069P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.148	(Δ/σ)_max = 0.003
S = 1.13	Δρ_max = 0.43 e Å⁻³
4456 reflections	Δρ_min = −0.44 e Å⁻³
278 parameters

Crystal data top

C₂₁H₂₀N₄O₄	V = 1854.6 (8) Å³
M_r = 392.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.852 (2) Å	µ = 0.1 mm⁻¹
b = 12.538 (3) Å	T = 298 K
c = 17.259 (4) Å	0.15 × 0.11 × 0.1 mm
β = 104.483 (18)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.081	0 restraints
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.43 e Å⁻³
4456 reflections	Δρ_min = −0.44 e Å⁻³
278 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	1.0239 (3)	0.62989 (17)	0.65204 (12)	0.0446 (5)
O2	1.0451 (3)	0.60240 (17)	0.43863 (13)	0.0463 (6)
O3	0.7614 (3)	0.63921 (19)	0.18421 (13)	0.0522 (6)
O4	0.6359 (3)	0.85414 (18)	0.36650 (13)	0.0520 (6)
N1	0.8229 (3)	0.6195 (2)	0.54163 (15)	0.0417 (6)
H1B	0.809 (5)	0.559 (4)	0.553 (3)	0.076 (14)*
N2	0.9943 (3)	0.7595 (2)	0.55764 (14)	0.0403 (6)
H2B	1.069 (4)	0.787 (3)	0.582 (2)	0.046 (10)*
N3	0.8909 (3)	0.6150 (2)	0.31407 (15)	0.0393 (6)
H3	0.936 (4)	0.563 (3)	0.3020 (19)	0.032 (8)*
N4	0.7093 (3)	0.7516 (2)	0.27656 (14)	0.0381 (6)
H4D	0.646 (4)	0.787 (3)	0.239 (2)	0.045 (9)*
C1	0.4632 (4)	0.5999 (3)	0.3870 (2)	0.0453 (7)
H1	0.4228	0.6665	0.3944	0.054*
C2	0.3664 (4)	0.5232 (3)	0.3421 (2)	0.0516 (8)
H2	0.2622	0.5397	0.3196	0.062*
C3	0.4211 (4)	0.4227 (3)	0.33000 (18)	0.0455 (7)
C4	0.3157 (5)	0.3384 (3)	0.2819 (2)	0.0634 (10)
H4A	0.3123	0.2776	0.3152	0.076*
H4B	0.3556	0.3172	0.2374	0.076*
H4C	0.2125	0.3668	0.2626	0.076*
C5	0.5765 (4)	0.4012 (3)	0.3651 (2)	0.0489 (8)
H5	0.6162	0.334	0.3587	0.059*
C6	0.6746 (4)	0.4773 (2)	0.40958 (19)	0.0448 (7)
H6	0.7787	0.4606	0.432	0.054*
C7	0.6191 (3)	0.5784 (2)	0.42101 (16)	0.0363 (6)
C8	0.7243 (3)	0.6631 (2)	0.46862 (16)	0.0357 (6)
H8	0.6568	0.7166	0.4842	0.043*
C9	0.9505 (4)	0.6683 (2)	0.58658 (16)	0.0361 (6)
C10	0.9253 (3)	0.8080 (2)	0.48001 (16)	0.0349 (6)
H10	0.8511	0.8621	0.4885	0.042*
C11	1.0480 (4)	0.8656 (2)	0.44822 (17)	0.0374 (7)
C12	1.0027 (4)	0.9543 (2)	0.39888 (18)	0.0417 (7)
H12	0.8984	0.9746	0.3844	0.05*
C13	1.1118 (4)	1.0120 (2)	0.3715 (2)	0.0491 (8)
H13	1.0792	1.0695	0.3374	0.059*
C14	1.2688 (4)	0.9861 (2)	0.3938 (2)	0.0474 (8)
C15	1.3894 (5)	1.0521 (3)	0.3674 (3)	0.0694 (11)
H15A	1.3866	1.124	0.3862	0.083*
H15B	1.3673	1.0521	0.3101	0.083*
H15C	1.4911	1.0224	0.3892	0.083*
C16	1.3123 (4)	0.8966 (3)	0.4421 (2)	0.0511 (8)
H16	1.4168	0.8768	0.4568	0.061*
C17	1.2051 (4)	0.8368 (3)	0.46843 (19)	0.0455 (8)
H17	1.2375	0.7769	0.4999	0.055*
C18	0.8296 (3)	0.7230 (2)	0.42113 (15)	0.0340 (6)
C19	0.9342 (3)	0.6434 (2)	0.39333 (16)	0.0335 (6)
C20	0.7848 (3)	0.6665 (2)	0.25345 (17)	0.0356 (6)
C21	0.7178 (3)	0.7831 (2)	0.35308 (16)	0.0343 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0555 (13)	0.0453 (11)	0.0249 (10)	−0.0030 (10)	−0.0049 (9)	0.0011 (8)
O2	0.0490 (13)	0.0443 (11)	0.0358 (11)	0.0170 (10)	−0.0075 (10)	−0.0017 (9)
O3	0.0634 (15)	0.0587 (14)	0.0279 (11)	0.0076 (12)	−0.0013 (10)	−0.0114 (10)
O4	0.0593 (14)	0.0517 (13)	0.0381 (12)	0.0261 (11)	−0.0007 (10)	−0.0024 (10)
N1	0.0491 (15)	0.0430 (14)	0.0264 (12)	−0.0046 (12)	−0.0030 (11)	0.0014 (10)
N2	0.0495 (15)	0.0402 (13)	0.0231 (11)	−0.0030 (12)	−0.0059 (11)	−0.0012 (10)
N3	0.0442 (14)	0.0381 (13)	0.0312 (13)	0.0117 (11)	0.0012 (10)	−0.0082 (10)
N4	0.0440 (14)	0.0405 (13)	0.0233 (11)	0.0111 (11)	−0.0040 (10)	0.0010 (10)
C1	0.0410 (16)	0.0415 (16)	0.0491 (19)	0.0038 (13)	0.0031 (14)	−0.0023 (13)
C2	0.0364 (16)	0.059 (2)	0.053 (2)	−0.0003 (15)	−0.0014 (14)	0.0024 (16)
C3	0.0520 (19)	0.0473 (17)	0.0335 (15)	−0.0100 (14)	0.0041 (14)	0.0023 (13)
C4	0.070 (2)	0.051 (2)	0.060 (2)	−0.0199 (18)	0.0006 (19)	−0.0005 (17)
C5	0.059 (2)	0.0394 (16)	0.0446 (18)	0.0011 (15)	0.0052 (15)	−0.0016 (13)
C6	0.0437 (17)	0.0436 (16)	0.0422 (17)	0.0069 (13)	0.0012 (14)	−0.0002 (13)
C7	0.0394 (15)	0.0402 (15)	0.0259 (13)	0.0013 (12)	0.0017 (11)	0.0023 (11)
C8	0.0411 (15)	0.0398 (14)	0.0231 (12)	0.0060 (12)	0.0023 (11)	−0.0020 (11)
C9	0.0441 (16)	0.0401 (14)	0.0214 (12)	0.0050 (12)	0.0034 (11)	−0.0023 (11)
C10	0.0435 (15)	0.0327 (13)	0.0233 (13)	0.0067 (12)	−0.0014 (11)	−0.0034 (10)
C11	0.0508 (17)	0.0291 (13)	0.0283 (13)	0.0034 (12)	0.0025 (12)	−0.0022 (11)
C12	0.0504 (18)	0.0349 (14)	0.0375 (16)	0.0116 (13)	0.0067 (13)	0.0021 (12)
C13	0.072 (2)	0.0317 (14)	0.0444 (18)	0.0090 (15)	0.0163 (16)	0.0030 (13)
C14	0.058 (2)	0.0382 (15)	0.0455 (18)	0.0030 (14)	0.0127 (15)	−0.0037 (13)
C15	0.074 (3)	0.054 (2)	0.081 (3)	−0.007 (2)	0.021 (2)	0.009 (2)
C16	0.0467 (18)	0.0494 (18)	0.053 (2)	0.0031 (15)	0.0053 (15)	0.0036 (15)
C17	0.0488 (18)	0.0423 (16)	0.0401 (17)	0.0082 (14)	0.0012 (14)	0.0065 (13)
C18	0.0415 (15)	0.0334 (13)	0.0221 (12)	0.0081 (12)	−0.0018 (11)	−0.0019 (10)
C19	0.0374 (15)	0.0328 (13)	0.0263 (13)	0.0054 (11)	0.0001 (11)	−0.0011 (10)
C20	0.0372 (15)	0.0376 (14)	0.0277 (13)	−0.0025 (12)	0.0002 (11)	−0.0015 (11)
C21	0.0367 (14)	0.0347 (13)	0.0265 (13)	0.0078 (12)	−0.0013 (11)	0.0006 (11)

Geometric parameters (Å, º) top

C1—C7	1.384 (4)	C11—C12	1.398 (4)
C1—C2	1.388 (5)	C12—C13	1.381 (5)
C1—H1	0.93	C12—H12	0.93
C2—C3	1.385 (5)	C13—C14	1.384 (5)
C2—H2	0.93	C13—H13	0.93
C3—C5	1.384 (5)	C14—C16	1.393 (5)
C3—C4	1.513 (5)	C14—C15	1.509 (5)
C4—H4A	0.96	C15—H15A	0.96
C4—H4B	0.96	C15—H15B	0.96
C4—H4C	0.96	C15—H15C	0.96
C5—C6	1.385 (4)	C16—C17	1.372 (5)
C5—H5	0.93	C16—H16	0.93
C6—C7	1.390 (4)	C17—H17	0.93
C6—H6	0.93	C18—C19	1.518 (4)
C7—C8	1.512 (4)	C18—C21	1.531 (4)
C8—N1	1.449 (4)	C19—O2	1.207 (3)
C8—C18	1.577 (4)	C19—N3	1.372 (3)
C8—H8	0.98	C20—O3	1.210 (3)
C9—O1	1.250 (3)	C20—N4	1.370 (4)
C9—N2	1.344 (4)	C20—N3	1.379 (4)
C9—N1	1.346 (4)	C21—O4	1.207 (3)
C10—N2	1.459 (3)	C21—N4	1.362 (4)
C10—C11	1.516 (4)	N1—H1B	0.80 (5)
C10—C18	1.568 (4)	N2—H2B	0.77 (4)
C10—H10	0.98	N3—H3	0.82 (3)
C11—C17	1.393 (4)	N4—H4D	0.87 (4)

C7—C1—C2	120.8 (3)	C12—C13—C14	121.4 (3)
C7—C1—H1	119.6	C12—C13—H13	119.3
C2—C1—H1	119.6	C14—C13—H13	119.3
C3—C2—C1	121.6 (3)	C13—C14—C16	117.6 (3)
C3—C2—H2	119.2	C13—C14—C15	121.6 (3)
C1—C2—H2	119.2	C16—C14—C15	120.8 (3)
C5—C3—C2	117.2 (3)	C14—C15—H15A	109.5
C5—C3—C4	120.9 (3)	C14—C15—H15B	109.5
C2—C3—C4	121.9 (3)	H15A—C15—H15B	109.5
C3—C4—H4A	109.5	C14—C15—H15C	109.5
C3—C4—H4B	109.5	H15A—C15—H15C	109.5
H4A—C4—H4B	109.5	H15B—C15—H15C	109.5
C3—C4—H4C	109.5	C17—C16—C14	121.8 (3)
H4A—C4—H4C	109.5	C17—C16—H16	119.1
H4B—C4—H4C	109.5	C14—C16—H16	119.1
C3—C5—C6	121.7 (3)	C16—C17—C11	120.3 (3)
C3—C5—H5	119.2	C16—C17—H17	119.8
C6—C5—H5	119.2	C11—C17—H17	119.8
C5—C6—C7	120.8 (3)	C19—C18—C21	114.1 (2)
C5—C6—H6	119.6	C19—C18—C10	112.2 (2)
C7—C6—H6	119.6	C21—C18—C10	107.7 (2)
C1—C7—C6	117.9 (3)	C19—C18—C8	109.7 (2)
C1—C7—C8	120.4 (3)	C21—C18—C8	106.3 (2)
C6—C7—C8	121.7 (3)	C10—C18—C8	106.3 (2)
N1—C8—C7	111.3 (2)	O2—C19—N3	121.0 (3)
N1—C8—C18	109.0 (2)	O2—C19—C18	122.5 (2)
C7—C8—C18	114.6 (2)	N3—C19—C18	116.5 (2)
N1—C8—H8	107.2	O3—C20—N4	122.2 (3)
C7—C8—H8	107.2	O3—C20—N3	122.1 (3)
C18—C8—H8	107.2	N4—C20—N3	115.7 (2)
O1—C9—N2	122.1 (3)	O4—C21—N4	120.6 (2)
O1—C9—N1	121.1 (3)	O4—C21—C18	121.3 (3)
N2—C9—N1	116.8 (3)	N4—C21—C18	118.0 (2)
N2—C10—C11	110.9 (2)	C9—N1—C8	124.5 (3)
N2—C10—C18	110.2 (2)	C9—N1—H1B	117 (3)
C11—C10—C18	114.1 (2)	C8—N1—H1B	118 (3)
N2—C10—H10	107	C9—N2—C10	127.1 (3)
C11—C10—H10	107	C9—N2—H2B	118 (3)
C18—C10—H10	107	C10—N2—H2B	114 (3)
C17—C11—C12	118.3 (3)	C19—N3—C20	127.0 (3)
C17—C11—C10	123.1 (3)	C19—N3—H3	115 (2)
C12—C11—C10	118.5 (3)	C20—N3—H3	118 (2)
C13—C12—C11	120.4 (3)	C21—N4—C20	126.5 (2)
C13—C12—H12	119.8	C21—N4—H4D	117 (2)
C11—C12—H12	119.8	C20—N4—H4D	117 (2)

C7—C1—C2—C3	0.4 (5)	N1—C8—C18—C19	65.8 (3)
C1—C2—C3—C5	0.5 (5)	C7—C8—C18—C19	−59.7 (3)
C1—C2—C3—C4	179.3 (4)	N1—C8—C18—C21	−170.3 (2)
C2—C3—C5—C6	−1.0 (5)	C7—C8—C18—C21	64.2 (3)
C4—C3—C5—C6	−179.8 (3)	N1—C8—C18—C10	−55.8 (3)
C3—C5—C6—C7	0.5 (5)	C7—C8—C18—C10	178.7 (2)
C2—C1—C7—C6	−0.8 (5)	C21—C18—C19—O2	167.7 (3)
C2—C1—C7—C8	178.9 (3)	C10—C18—C19—O2	44.8 (4)
C5—C6—C7—C1	0.4 (5)	C8—C18—C19—O2	−73.1 (3)
C5—C6—C7—C8	−179.4 (3)	C21—C18—C19—N3	−16.2 (4)
C1—C7—C8—N1	136.0 (3)	C10—C18—C19—N3	−139.0 (3)
C6—C7—C8—N1	−44.2 (4)	C8—C18—C19—N3	103.0 (3)
C1—C7—C8—C18	−99.7 (3)	C19—C18—C21—O4	−174.6 (3)
C6—C7—C8—C18	80.0 (3)	C10—C18—C21—O4	−49.3 (4)
N2—C10—C11—C17	27.2 (4)	C8—C18—C21—O4	64.3 (3)
C18—C10—C11—C17	−98.0 (3)	C19—C18—C21—N4	7.6 (4)
N2—C10—C11—C12	−150.1 (3)	C10—C18—C21—N4	132.9 (3)
C18—C10—C11—C12	84.6 (3)	C8—C18—C21—N4	−113.5 (3)
C17—C11—C12—C13	−0.4 (4)	O1—C9—N1—C8	174.7 (3)
C10—C11—C12—C13	177.0 (3)	N2—C9—N1—C8	−5.4 (5)
C11—C12—C13—C14	−1.9 (5)	C7—C8—N1—C9	164.5 (3)
C12—C13—C14—C16	2.8 (5)	C18—C8—N1—C9	37.2 (4)
C12—C13—C14—C15	−176.9 (3)	O1—C9—N2—C10	175.3 (3)
C13—C14—C16—C17	−1.4 (5)	N1—C9—N2—C10	−4.6 (5)
C15—C14—C16—C17	178.4 (4)	C11—C10—N2—C9	−146.8 (3)
C14—C16—C17—C11	−0.9 (5)	C18—C10—N2—C9	−19.4 (4)
C12—C11—C17—C16	1.8 (5)	O2—C19—N3—C20	−168.4 (3)
C10—C11—C17—C16	−175.5 (3)	C18—C19—N3—C20	15.4 (4)
N2—C10—C18—C19	−72.4 (3)	O3—C20—N3—C19	175.2 (3)
C11—C10—C18—C19	53.3 (3)	N4—C20—N3—C19	−3.9 (5)
N2—C10—C18—C21	161.2 (2)	O4—C21—N4—C20	−173.8 (3)
C11—C10—C18—C21	−73.2 (3)	C18—C21—N4—C20	4.0 (4)
N2—C10—C18—C8	47.6 (3)	O3—C20—N4—C21	174.2 (3)
C11—C10—C18—C8	173.3 (2)	N3—C20—N4—C21	−6.7 (4)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1/2, −y+3/2, z+1/2; (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+3/2, y−1/2, −z+1/2; (v) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀N₄O₄
M_r	392.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.852 (2), 12.538 (3), 17.259 (4)
β (°)	104.483 (18)
V (Å³)	1854.6 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.1
Crystal size (mm)	0.15 × 0.11 × 0.1

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Numerical shape of crystal determined optically (X-SHAPE; Stoe & Cie, 2005))
T_min, T_max	0.979, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	17766, 4456, 3107
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.081, 0.148, 1.13
No. of reflections	4456
No. of parameters	278
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.44

Computer programs: X-AREA (Stoe & Cie, 2005), X-RED (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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	3.018	3.721 (3)	131
C10—H10···Cg4^v	0.98	3.106	3.914 (3)	141

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1/2, −y+3/2, z+1/2; (iii) x−1/2, −y+3/2, z−1/2; (iv) −x+3/2, y−1/2, −z+1/2; (v) −x+1, −y+1, −z.

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. CrossRef Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Kazmierski, W. M., Furfine, E., Spaltenstein, A. & Wright, L. L. (2006). Bioorg. Med. Chem. Lett. 16, 5226–5230. Web of Science CrossRef PubMed CAS Google Scholar
Pradhan, R., Patra, M., Behera, A. K., Mishra, B. K. & Behera, R. K. (2006). Tetrahedron, 62, 779–828. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2005). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany. Google Scholar
Useglio, M., Castellano, P. M., Operto, M. A., Torres, R. & Kaufmen, T. S. (2006). Bioorg. Med. Chem. Lett. 16, 5097–5101. Web of Science CrossRef PubMed CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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