1,1′,3,3′,5,5′-Hexamethyl­spiro­[furo[2,3-d]pyrimidine-6(5H),5′-pyrimidine]-2,2′,4,4′,6′(1H,3H,1′H,3′H,5′H)-penta­one

Noroozi Pesyan, N.; Rastgar, S.; Hosseini, Y.

doi:10.1107/S1600536809019618

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1444

doi:10.1107/S1600536809019618

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1,1′,3,3′,5,5′-Hexamethylspiro[furo[2,3-d]pyrimidine-6(5H),5′-pyrimidine]-2,2′,4,4′,6′(1H,3H,1′H,3′H,5′H)-pentaone

Nader Noroozi Pesyan,^a ^* Saeed Rastgar ^a and Yaser Hosseini ^a

^aDepartment of Chemistry, Faculty of Science, Urmia University, 57159 Urmia, Iran
^*Correspondence e-mail: pesyan@gmail.com

(Received 21 April 2009; accepted 23 May 2009; online 29 May 2009)

In the title molecule, C₁₅H₁₈N₄O₆, the fused 2,3-dihydrofuran ring has an envelope conformation and the spiro pyrimidine ring has a half-chair conformation. In the crystal, short intermolecular O⋯C contacts of 2.835 (4) and 2.868 (4) Å between the carbonyl groups indicate the existence of electrostatic interactions, which link the molecules into corrugated sheets parallel to the ab plane.

Related literature

For applications of furo[2,3-d]pyrimidine derivatives, see Cody et al. (1997 ). For a related crystal structure, see Malathy Sony et al. (2002 ).

Experimental

Crystal data

C₁₅H₁₈N₄O₆
M_r = 350.33
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.0122 (9) Å
b = 11.9181 (14) Å
c = 16.4037 (19) Å
V = 1566.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 120 K
0.21 × 0.14 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.980, T_max = 0.989
15042 measured reflections
1964 independent reflections
1589 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.089
S = 1.01
1964 reflections
232 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Selected interatomic distances (Å)

C8⋯O2ⁱ	2.835 (4)
C3⋯O5ⁱⁱ	2.868 (4)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x+1, y, z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019618/cv2553sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019618/cv2553Isup2.hkl

checkCIF report

Comment top

Fused pyrimidine compounds are valued in view of their well-known biological properties. As example, the furo[2,3-d]pyrimidine antifolate derivative introduced as novel classical antitumor agent (Cody et al., 1997). Herewith we present the title compound, (I).

In (I) (Fig. 1),the fused 2,3-dihydrofuran ring has an envelope conformation, and spiro pyrimidine ring has a half-chair conformation. Spiro pyrimidine ring is nearly perpendicular to 2,3-dihydro furan ring moiety, as was observed earlier in the related compound (Malathy Sony et al., 2002). Torsion angles C2–C1–O4–C7 and C2–C1–C5–C6 are -99.39 (3)° and 94.87 (3)°, respectively. In the crystal, short intermolecular O···C contacts (Table 1) between the carbonyl groups prove an existing of electrostatic interactions, which link the molecules into corrugated sheets parallel to ab plane.

Related literature top

For applications of furo[2,3-d]pyrimidine derivatives, see Cody et al. (1997). For a related crystal structure, see Malathy Sony et al. (2002).

Experimental top

In a 50 ml round bottom flask (in an ice-bath) equipped with magnetic stirrer was added 200 mg (1.89 mmol) cyanogen bromide in 10 ml acetone. Then a solution of 295 mg (1.89 mmol) 1,3-dimethylbarbituric acid and 202 mg (2.00 mmol) triethylamine in acetone was added drop wise by reparatory funnel during 1 h. The white solid precipitated after few minutes and the color of liquid turned red. Initially, the precipitate was dissolved in acetone. A white crystalline colorless solid was formed after allowing the solution to stand overnight (228 mg, 50% yield) as a white crystalline solid, m.p. 210–212 °C (decomps.); FT—IR (KBr), ν, cm^-1: 2981.54, 2954.71, 1689.08, 1646.35; ¹H NMR(CDCl₃, 300 MHz) δ 3.434 (s, 3H); 3.355 (s, 6H), 3.283 (s, 3H), 1.402 (s,6H); ¹³C NMR (CDCl₃, 75 MHz) δ 164.317, 160.207, 158.898, 151.033, 150.145, 93.220, 91.139, 53.872, 29.625, 29.081, 27.852, 23.318.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing the atomic numbering and 50% probability displacement ellipsoids.

1,1',3,3',5,5'-Hexamethylspiro[furo[2,3-d]pyrimidine-6(5H),5'- pyrimidine]-2,2',4,4',6'(1H,3H,1'H,3'H,5'H)- pentaone top

Crystal data top

C₁₅H₁₈N₄O₆	D_x = 1.486 Mg m⁻³
M_r = 350.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 985 reflections
a = 8.0122 (9) Å	θ = 3–25°
b = 11.9181 (14) Å	µ = 0.12 mm⁻¹
c = 16.4037 (19) Å	T = 120 K
V = 1566.4 (3) Å³	Prism, white
Z = 4	0.21 × 0.14 × 0.12 mm
F(000) = 736

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1964 independent reflections
Radiation source: fine-focus sealed tube	1589 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −10→10
T_min = 0.980, T_max = 0.989	k = −15→15
15042 measured reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.01P)² + 2P] where P = (F_o² + 2F_c²)/3
1964 reflections	(Δ/σ)_max < 0.001
232 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₅H₁₈N₄O₆	V = 1566.4 (3) Å³
M_r = 350.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.0122 (9) Å	µ = 0.12 mm⁻¹
b = 11.9181 (14) Å	T = 120 K
c = 16.4037 (19) Å	0.21 × 0.14 × 0.12 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1964 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	1589 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.989	R_int = 0.041
15042 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.01	Δρ_max = 0.20 e Å⁻³
1964 reflections	Δρ_min = −0.22 e Å⁻³
232 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1	0.5464 (3)	0.52840 (19)	0.75372 (15)	0.0307 (6)
O2	0.8328 (3)	0.8456 (2)	0.69785 (15)	0.0358 (6)
O3	0.6235 (3)	0.7991 (2)	0.94992 (14)	0.0352 (6)
O4	0.4987 (3)	0.59548 (19)	0.90811 (15)	0.0262 (5)
O5	−0.0582 (3)	0.6474 (2)	0.83863 (15)	0.0333 (6)
O6	0.0962 (3)	0.3545 (2)	1.00229 (15)	0.0306 (6)
N1	0.6700 (4)	0.6929 (2)	0.71936 (16)	0.0247 (6)
N2	0.6981 (4)	0.8365 (2)	0.81937 (16)	0.0251 (6)
N4	0.0212 (3)	0.5008 (2)	0.92003 (17)	0.0242 (6)
N5	0.3017 (3)	0.4687 (2)	0.95490 (17)	0.0242 (6)
C1	0.5068 (4)	0.6811 (3)	0.84600 (19)	0.0229 (7)
C2	0.5782 (4)	0.6254 (3)	0.7708 (2)	0.0250 (7)
C3	0.7394 (4)	0.7956 (3)	0.7427 (2)	0.0254 (7)
C4	0.6170 (4)	0.7750 (3)	0.8785 (2)	0.0252 (7)
C5	0.3186 (4)	0.7229 (3)	0.8311 (2)	0.0276 (8)
C6	0.2301 (4)	0.6208 (3)	0.8654 (2)	0.0242 (7)
C7	0.3382 (4)	0.5599 (3)	0.9086 (2)	0.0236 (7)
C8	0.1355 (4)	0.4355 (3)	0.9614 (2)	0.0237 (7)
C9	0.0562 (4)	0.5958 (3)	0.8712 (2)	0.0258 (8)
C10	0.7301 (5)	0.6431 (3)	0.6434 (2)	0.0334 (8)
H10A	0.6364	0.6084	0.6143	0.050*
H10B	0.8142	0.5858	0.6557	0.050*
H10C	0.7799	0.7016	0.6092	0.050*
C11	0.7816 (5)	0.9384 (3)	0.8465 (2)	0.0321 (8)
H11A	0.7027	0.9851	0.8771	0.048*
H11B	0.8223	0.9802	0.7990	0.048*
H11C	0.8760	0.9186	0.8817	0.048*
C12	0.2810 (5)	0.7474 (3)	0.7410 (2)	0.0337 (9)
H12A	0.1620	0.7645	0.7346	0.051*
H12B	0.3095	0.6817	0.7079	0.051*
H12C	0.3474	0.8119	0.7229	0.051*
C13	0.2770 (5)	0.8270 (3)	0.8822 (2)	0.0358 (9)
H13A	0.1572	0.8428	0.8784	0.054*
H13B	0.3400	0.8915	0.8615	0.054*
H13C	0.3072	0.8134	0.9392	0.054*
C14	−0.1530 (4)	0.4664 (3)	0.9244 (2)	0.0326 (8)
H14A	−0.1596	0.3889	0.9442	0.049*
H14B	−0.2034	0.4712	0.8701	0.049*
H14C	−0.2133	0.5159	0.9619	0.049*
C15	0.4309 (4)	0.3990 (3)	0.9914 (2)	0.0303 (8)
H15A	0.5206	0.4469	1.0123	0.045*
H15B	0.4760	0.3479	0.9501	0.045*
H15C	0.3830	0.3553	1.0363	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0313 (14)	0.0252 (12)	0.0355 (13)	−0.0023 (11)	0.0011 (12)	−0.0009 (11)
O2	0.0412 (15)	0.0304 (13)	0.0357 (14)	−0.0072 (13)	0.0071 (12)	0.0047 (11)
O3	0.0416 (16)	0.0377 (14)	0.0262 (12)	−0.0048 (13)	0.0006 (12)	−0.0017 (11)
O4	0.0207 (12)	0.0275 (12)	0.0304 (12)	−0.0015 (10)	−0.0002 (10)	0.0055 (11)
O5	0.0240 (12)	0.0359 (14)	0.0399 (14)	0.0027 (12)	−0.0043 (12)	0.0057 (12)
O6	0.0257 (13)	0.0307 (13)	0.0353 (13)	−0.0014 (11)	0.0014 (12)	0.0063 (12)
N1	0.0264 (15)	0.0257 (14)	0.0221 (13)	0.0007 (13)	0.0016 (12)	0.0010 (11)
N2	0.0262 (15)	0.0225 (14)	0.0267 (14)	−0.0013 (12)	0.0014 (13)	0.0002 (12)
N4	0.0215 (14)	0.0243 (14)	0.0269 (14)	0.0011 (12)	0.0009 (12)	−0.0002 (12)
N5	0.0228 (15)	0.0228 (14)	0.0268 (14)	0.0009 (12)	0.0004 (13)	0.0025 (12)
C1	0.0207 (15)	0.0247 (16)	0.0234 (16)	−0.0003 (14)	0.0014 (14)	0.0014 (14)
C2	0.0215 (16)	0.0264 (17)	0.0272 (17)	0.0033 (15)	−0.0023 (15)	0.0004 (15)
C3	0.0258 (18)	0.0242 (16)	0.0262 (16)	−0.0007 (15)	−0.0021 (15)	0.0017 (14)
C4	0.0227 (17)	0.0257 (17)	0.0274 (17)	0.0034 (14)	0.0007 (14)	0.0008 (14)
C5	0.0196 (16)	0.0285 (18)	0.0346 (18)	0.0030 (15)	0.0035 (15)	0.0044 (15)
C6	0.0218 (16)	0.0252 (17)	0.0255 (16)	0.0005 (14)	0.0028 (14)	0.0021 (14)
C7	0.0224 (17)	0.0210 (16)	0.0275 (17)	−0.0015 (15)	0.0016 (15)	−0.0016 (14)
C8	0.0225 (17)	0.0243 (17)	0.0244 (16)	0.0015 (15)	0.0015 (14)	−0.0005 (15)
C9	0.0267 (18)	0.0261 (18)	0.0248 (17)	0.0020 (15)	0.0005 (15)	−0.0016 (15)
C10	0.039 (2)	0.0317 (19)	0.0296 (18)	0.0008 (18)	0.0025 (17)	−0.0012 (16)
C11	0.0331 (19)	0.0269 (18)	0.0363 (19)	−0.0054 (16)	0.0001 (17)	−0.0015 (16)
C12	0.0284 (19)	0.0342 (19)	0.038 (2)	0.0031 (17)	−0.0037 (17)	0.0085 (17)
C13	0.0293 (19)	0.0268 (18)	0.051 (2)	0.0024 (16)	0.0097 (19)	0.0012 (18)
C14	0.0195 (17)	0.038 (2)	0.040 (2)	−0.0035 (17)	0.0002 (16)	0.0034 (17)
C15	0.0242 (17)	0.0302 (19)	0.0364 (19)	0.0043 (16)	−0.0023 (17)	0.0091 (16)

Geometric parameters (Å, º) top

O1—C2	1.216 (4)	C5—C13	1.534 (5)
O2—C3	1.206 (4)	C5—C12	1.537 (5)
O3—C4	1.208 (4)	C6—C7	1.334 (5)
O4—C7	1.354 (4)	C6—C9	1.428 (5)
O4—C1	1.443 (4)	C10—H10A	0.9800
O5—C9	1.226 (4)	C10—H10B	0.9800
O6—C8	1.217 (4)	C10—H10C	0.9800
N1—C2	1.378 (4)	C11—H11A	0.9800
N1—C3	1.399 (4)	C11—H11B	0.9800
N1—C10	1.462 (4)	C11—H11C	0.9800
N2—C4	1.378 (4)	C12—H12A	0.9800
N2—C3	1.389 (4)	C12—H12B	0.9800
N2—C11	1.457 (4)	C12—H12C	0.9800
N4—C8	1.380 (4)	C13—H13A	0.9800
N4—C9	1.416 (4)	C13—H13B	0.9800
N4—C14	1.457 (4)	C13—H13C	0.9800
N5—C7	1.358 (4)	C14—H14A	0.9800
N5—C8	1.393 (4)	C14—H14B	0.9800
N5—C15	1.456 (4)	C14—H14C	0.9800
C1—C2	1.513 (4)	C15—H15A	0.9800
C1—C4	1.522 (5)	C15—H15B	0.9800
C1—C5	1.607 (5)	C15—H15C	0.9800
C5—C6	1.516 (5)

C8···O2ⁱ	2.835 (4)	C3···O5ⁱⁱ	2.868 (4)

C7—O4—C1	105.6 (3)	O6—C8—N5	121.0 (3)
C2—N1—C3	123.8 (3)	N4—C8—N5	115.8 (3)
C2—N1—C10	117.4 (3)	O5—C9—N4	120.0 (3)
C3—N1—C10	117.2 (3)	O5—C9—C6	126.6 (3)
C4—N2—C3	124.3 (3)	N4—C9—C6	113.4 (3)
C4—N2—C11	116.4 (3)	N1—C10—H10A	109.5
C3—N2—C11	117.3 (3)	N1—C10—H10B	109.5
C8—N4—C9	126.8 (3)	H10A—C10—H10B	109.5
C8—N4—C14	116.9 (3)	N1—C10—H10C	109.5
C9—N4—C14	116.3 (3)	H10A—C10—H10C	109.5
C7—N5—C8	118.5 (3)	H10B—C10—H10C	109.5
C7—N5—C15	122.2 (3)	N2—C11—H11A	109.5
C8—N5—C15	119.1 (3)	N2—C11—H11B	109.5
O4—C1—C2	106.4 (3)	H11A—C11—H11B	109.5
O4—C1—C4	107.4 (3)	N2—C11—H11C	109.5
C2—C1—C4	112.9 (3)	H11A—C11—H11C	109.5
O4—C1—C5	106.5 (3)	H11B—C11—H11C	109.5
C2—C1—C5	111.5 (3)	C5—C12—H12A	109.5
C4—C1—C5	111.7 (3)	C5—C12—H12B	109.5
O1—C2—N1	121.7 (3)	H12A—C12—H12B	109.5
O1—C2—C1	121.7 (3)	C5—C12—H12C	109.5
N1—C2—C1	116.4 (3)	H12A—C12—H12C	109.5
O2—C3—N2	121.8 (3)	H12B—C12—H12C	109.5
O2—C3—N1	120.8 (3)	C5—C13—H13A	109.5
N2—C3—N1	117.3 (3)	C5—C13—H13B	109.5
O3—C4—N2	122.4 (3)	H13A—C13—H13B	109.5
O3—C4—C1	122.6 (3)	C5—C13—H13C	109.5
N2—C4—C1	114.7 (3)	H13A—C13—H13C	109.5
C6—C5—C13	110.2 (3)	H13B—C13—H13C	109.5
C6—C5—C12	114.7 (3)	N4—C14—H14A	109.5
C13—C5—C12	109.2 (3)	N4—C14—H14B	109.5
C6—C5—C1	97.7 (3)	H14A—C14—H14B	109.5
C13—C5—C1	111.8 (3)	N4—C14—H14C	109.5
C12—C5—C1	112.9 (3)	H14A—C14—H14C	109.5
C7—C6—C9	119.0 (3)	H14B—C14—H14C	109.5
C7—C6—C5	109.3 (3)	N5—C15—H15A	109.5
C9—C6—C5	130.4 (3)	N5—C15—H15B	109.5
C6—C7—O4	116.3 (3)	H15A—C15—H15B	109.5
C6—C7—N5	126.4 (3)	N5—C15—H15C	109.5
O4—C7—N5	117.3 (3)	H15A—C15—H15C	109.5
O6—C8—N4	123.1 (3)	H15B—C15—H15C	109.5

C7—O4—C1—C2	−99.4 (3)	C4—C1—C5—C13	−22.4 (4)
C7—O4—C1—C4	139.5 (3)	O4—C1—C5—C12	−141.8 (3)
C7—O4—C1—C5	19.7 (3)	C2—C1—C5—C12	−26.1 (4)
C3—N1—C2—O1	−166.1 (3)	C4—C1—C5—C12	101.2 (3)
C10—N1—C2—O1	−0.8 (5)	C13—C5—C6—C7	−101.6 (3)
C3—N1—C2—C1	19.0 (5)	C12—C5—C6—C7	134.8 (3)
C10—N1—C2—C1	−175.7 (3)	C1—C5—C6—C7	15.1 (4)
O4—C1—C2—O1	35.2 (4)	C13—C5—C6—C9	64.9 (5)
C4—C1—C2—O1	152.8 (3)	C12—C5—C6—C9	−58.7 (5)
C5—C1—C2—O1	−80.6 (4)	C1—C5—C6—C9	−178.4 (4)
O4—C1—C2—N1	−149.9 (3)	C9—C6—C7—O4	−172.6 (3)
C4—C1—C2—N1	−32.3 (4)	C5—C6—C7—O4	−4.3 (4)
C5—C1—C2—N1	94.4 (3)	C9—C6—C7—N5	4.8 (5)
C4—N2—C3—O2	−168.0 (3)	C5—C6—C7—N5	173.1 (3)
C11—N2—C3—O2	−4.5 (5)	C1—O4—C7—C6	−10.5 (4)
C4—N2—C3—N1	11.2 (5)	C1—O4—C7—N5	171.8 (3)
C11—N2—C3—N1	174.8 (3)	C8—N5—C7—C6	−2.2 (5)
C2—N1—C3—O2	172.2 (3)	C15—N5—C7—C6	171.9 (3)
C10—N1—C3—O2	6.9 (5)	C8—N5—C7—O4	175.2 (3)
C2—N1—C3—N2	−7.0 (5)	C15—N5—C7—O4	−10.7 (5)
C10—N1—C3—N2	−172.3 (3)	C9—N4—C8—O6	−179.9 (3)
C3—N2—C4—O3	158.8 (3)	C14—N4—C8—O6	−2.3 (5)
C11—N2—C4—O3	−4.9 (5)	C9—N4—C8—N5	1.2 (5)
C3—N2—C4—C1	−26.5 (5)	C14—N4—C8—N5	178.7 (3)
C11—N2—C4—C1	169.9 (3)	C7—N5—C8—O6	−179.8 (3)
O4—C1—C4—O3	−32.7 (4)	C15—N5—C8—O6	5.9 (5)
C2—C1—C4—O3	−149.7 (3)	C7—N5—C8—N4	−0.9 (5)
C5—C1—C4—O3	83.7 (4)	C15—N5—C8—N4	−175.1 (3)
O4—C1—C4—N2	152.5 (3)	C8—N4—C9—O5	−179.0 (3)
C2—C1—C4—N2	35.5 (4)	C14—N4—C9—O5	3.5 (5)
C5—C1—C4—N2	−91.1 (3)	C8—N4—C9—C6	1.3 (5)
O4—C1—C5—C6	−20.8 (3)	C14—N4—C9—C6	−176.3 (3)
C2—C1—C5—C6	94.9 (3)	C7—C6—C9—O5	176.2 (3)
C4—C1—C5—C6	−137.8 (3)	C5—C6—C9—O5	10.8 (6)
O4—C1—C5—C13	94.6 (3)	C7—C6—C9—N4	−4.1 (5)
C2—C1—C5—C13	−149.7 (3)	C5—C6—C9—N4	−169.5 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₈N₄O₆
M_r	350.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	120
a, b, c (Å)	8.0122 (9), 11.9181 (14), 16.4037 (19)
V (Å³)	1566.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.21 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.980, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	15042, 1964, 1589
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.089, 1.01
No. of reflections	1964
No. of parameters	232
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Selected interatomic distances (Å) top

C8···O2ⁱ

2.835 (4)

C3···O5ⁱⁱ

2.868 (4)

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

Acknowledgements

This work was supported by the Urmia University Research Council. We also thank Professor M. Yu. Antipin and Dr Z. Starikova for the X-ray data collection at the X-ray Structural Centre (XRSC), Moscow, Russia.

References

Bruker (1998). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cody, V., Galitsky, N., Luft, J. R., Pangborn, W., Gangjee, A., Devraj, R., Queener, S. F. & Blakley, R. L. (1997). Acta Cryst. D53, 638–649. CrossRef CAS Web of Science IUCr Journals Google Scholar
Malathy Sony, S. M., Kuppayee, M., Ponnuswamy, M. N., Bhasker Reddy, D., Padmavathi, V. & Fun, H.-K. (2002). Acta Cryst. C58, o678–o680. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

1,1′,3,3′,5,5′-Hexa­methyl­spiro­[furo[2,3-d]pyrimidine-6(5H),5′-pyrimidine]-2,2′,4,4′,6′(1H,3H,1′H,3′H,5′H)-penta­one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,1′,3,3′,5,5′-Hexamethylspiro[furo[2,3-d]pyrimidine-6(5H),5′-pyrimidine]-2,2′,4,4′,6′(1H,3H,1′H,3′H,5′H)-pentaone