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The title compound, C14H20N4O4, was prepared by [2+2]-photocyclo­addition of 1,3,6-tri­methyl­uracil in acetone. The structure determination was undertaken in order to determine the stereoconfiguration of the product, which could not be extracted from the NMR data. Single-crystal X-ray analysis revealed that the methyl groups are located on the same side of the cyclo­butane ring (cis) and that the monomers are oriented head-to-tail (anti).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004452/bt6119sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004452/bt6119Isup2.hkl
Contains datablock I

CCDC reference: 183792

Key indicators

  • Single-crystal X-ray study
  • T = 170 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.123
  • Data-to-parameter ratio = 16.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: IPDS Program Package (Stoe & Cie, 1998); cell refinement: IPDS Program Package; data reduction: IPDS Program Package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1998); software used to prepare material for publication: CIFTAB in SHELXL97.

(I) top
Crystal data top
C14H20N4O4F(000) = 656
Mr = 308.34Dx = 1.399 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.4422 (6) ÅCell parameters from 8000 reflections
b = 14.0159 (11) Åθ = 12.5–25°
c = 12.7803 (8) ŵ = 0.10 mm1
β = 104.445 (8)°T = 170 K
V = 1464.42 (18) Å3Irregular block, colourless
Z = 40.4 × 0.4 × 0.3 mm
Data collection top
Stoe Imaging Plate Diffraction System
diffractometer
3097 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Graphite monochromatorθmax = 28.1°, θmin = 2.9°
φ scansh = 1111
13199 measured reflectionsk = 1818
3425 independent reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0703P)2 + 0.4649P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3425 reflectionsΔρmax = 0.22 e Å3
206 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.062 (9)
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
xyzUiso*/Ueq
N10.78205 (11)0.77535 (7)0.27455 (8)0.0223 (2)
C20.82012 (13)0.81311 (8)0.18684 (9)0.0222 (2)
N30.98191 (11)0.80661 (7)0.17689 (8)0.0255 (2)
C41.10800 (14)0.76536 (10)0.25232 (11)0.0310 (3)
C51.06109 (13)0.70991 (8)0.33868 (10)0.0252 (3)
H51.15180.71300.40600.030*
C60.89808 (13)0.73236 (8)0.36677 (9)0.0225 (2)
C110.61614 (14)0.79420 (9)0.28484 (11)0.0293 (3)
H11A0.60730.86110.30480.044*
H11B0.59240.75280.34090.044*
H11C0.53760.78130.21570.044*
O120.71846 (10)0.85375 (7)0.11585 (7)0.0322 (2)
C131.01550 (17)0.84967 (10)0.08004 (11)0.0328 (3)
H13A1.13260.84460.08380.049*
H13B0.98360.91710.07590.049*
H13C0.95280.81610.01570.049*
O141.24902 (13)0.77021 (11)0.24559 (11)0.0569 (4)
C160.90919 (17)0.78863 (9)0.46951 (10)0.0323 (3)
H16A0.93430.85540.45770.048*
H16B0.99590.76190.52790.048*
H16C0.80450.78500.48940.048*
N210.93405 (12)0.58422 (8)0.20110 (8)0.0261 (2)
C220.77692 (14)0.55781 (8)0.15779 (9)0.0247 (2)
N230.66775 (11)0.55754 (7)0.22449 (8)0.0245 (2)
C240.70751 (14)0.58192 (8)0.33151 (10)0.0238 (2)
C250.87438 (13)0.62150 (8)0.37562 (9)0.0226 (2)
H250.91540.60140.45270.027*
C261.00743 (13)0.60298 (8)0.31521 (9)0.0235 (2)
C311.04325 (17)0.57469 (12)0.12885 (12)0.0405 (3)
H31A1.06700.50710.12060.061*
H31B1.14550.60890.15950.061*
H31C0.99030.60170.05800.061*
O320.72897 (12)0.53444 (8)0.06336 (8)0.0383 (3)
C330.49735 (15)0.53062 (10)0.17606 (11)0.0328 (3)
H33A0.46770.47620.21540.049*
H33B0.48500.51300.10020.049*
H33C0.42550.58470.18020.049*
O340.60855 (12)0.57572 (7)0.38586 (8)0.0345 (2)
C361.13533 (16)0.52872 (10)0.36463 (11)0.0330 (3)
H36A1.08520.46520.35590.049*
H36B1.17870.54230.44170.049*
H36C1.22460.53070.32820.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0180 (4)0.0281 (5)0.0206 (5)0.0013 (3)0.0045 (3)0.0038 (3)
C20.0201 (5)0.0248 (5)0.0206 (6)0.0021 (4)0.0034 (4)0.0009 (4)
N30.0211 (5)0.0314 (5)0.0248 (5)0.0018 (4)0.0075 (4)0.0043 (4)
C40.0194 (5)0.0377 (7)0.0352 (7)0.0011 (4)0.0056 (5)0.0052 (5)
C50.0190 (5)0.0311 (6)0.0226 (6)0.0004 (4)0.0003 (4)0.0014 (4)
C60.0226 (5)0.0257 (5)0.0176 (6)0.0006 (4)0.0019 (4)0.0001 (4)
C110.0219 (5)0.0347 (6)0.0333 (7)0.0036 (4)0.0106 (5)0.0055 (5)
O120.0252 (4)0.0419 (5)0.0268 (5)0.0013 (3)0.0012 (3)0.0120 (4)
C130.0350 (6)0.0376 (7)0.0304 (7)0.0017 (5)0.0165 (5)0.0068 (5)
O140.0202 (5)0.0829 (9)0.0695 (9)0.0025 (5)0.0149 (5)0.0291 (7)
C160.0420 (7)0.0310 (6)0.0220 (6)0.0005 (5)0.0042 (5)0.0051 (5)
N210.0205 (5)0.0389 (6)0.0185 (5)0.0008 (4)0.0040 (4)0.0046 (4)
C220.0237 (5)0.0291 (5)0.0198 (6)0.0015 (4)0.0024 (4)0.0021 (4)
N230.0204 (5)0.0290 (5)0.0229 (5)0.0012 (3)0.0032 (4)0.0008 (4)
C240.0265 (5)0.0221 (5)0.0239 (6)0.0003 (4)0.0083 (4)0.0002 (4)
C250.0247 (5)0.0259 (5)0.0167 (5)0.0002 (4)0.0039 (4)0.0000 (4)
C260.0206 (5)0.0298 (6)0.0178 (6)0.0022 (4)0.0008 (4)0.0008 (4)
C310.0312 (6)0.0637 (9)0.0302 (7)0.0012 (6)0.0145 (5)0.0085 (6)
O320.0353 (5)0.0551 (6)0.0215 (5)0.0048 (4)0.0017 (4)0.0092 (4)
C330.0227 (6)0.0376 (7)0.0347 (7)0.0056 (5)0.0008 (5)0.0008 (5)
O340.0366 (5)0.0366 (5)0.0363 (6)0.0054 (4)0.0205 (4)0.0030 (4)
C360.0294 (6)0.0342 (6)0.0314 (7)0.0084 (5)0.0002 (5)0.0008 (5)
Geometric parameters (Å, º) top
N1—C21.3490 (14)C16—H16C0.9800
N1—C61.4613 (14)N21—C221.3553 (15)
N1—C111.4631 (14)N21—C261.4592 (15)
C2—O121.2230 (14)N21—C311.4645 (15)
C2—N31.4060 (14)C22—O321.2182 (15)
N3—C41.3728 (16)C22—N231.4028 (15)
N3—C131.4670 (15)N23—C241.3680 (16)
C4—O141.2167 (16)N23—C331.4666 (15)
C4—C51.4822 (17)C24—O341.2155 (14)
C5—C61.5389 (15)C24—C251.4879 (16)
C5—C261.5727 (16)C25—C261.5355 (15)
C5—H51.0000C25—H251.0000
C6—C161.5145 (16)C26—C361.5192 (16)
C6—C251.5744 (15)C31—H31A0.9800
C11—H11A0.9800C31—H31B0.9800
C11—H11B0.9800C31—H31C0.9800
C11—H11C0.9800C33—H33A0.9800
C13—H13A0.9800C33—H33B0.9800
C13—H13B0.9800C33—H33C0.9800
C13—H13C0.9800C36—H36A0.9800
C16—H16A0.9800C36—H36B0.9800
C16—H16B0.9800C36—H36C0.9800
C2—N1—C6125.53 (9)C22—N21—C26125.85 (10)
C2—N1—C11115.83 (9)C22—N21—C31115.06 (11)
C6—N1—C11117.78 (9)C26—N21—C31118.00 (10)
O12—C2—N1122.05 (10)O32—C22—N21121.84 (11)
O12—C2—N3118.74 (10)O32—C22—N23119.67 (11)
N1—C2—N3119.20 (10)N21—C22—N23118.49 (10)
C4—N3—C2124.36 (10)C24—N23—C22124.92 (10)
C4—N3—C13119.12 (10)C24—N23—C33117.16 (10)
C2—N3—C13116.50 (10)C22—N23—C33117.92 (10)
O14—C4—N3121.86 (13)O34—C24—N23121.42 (11)
O14—C4—C5121.99 (12)O34—C24—C25122.07 (11)
N3—C4—C5116.06 (10)N23—C24—C25116.42 (10)
C4—C5—C6119.14 (10)C24—C25—C26119.26 (10)
C4—C5—C26118.38 (11)C24—C25—C6117.78 (9)
C6—C5—C2690.43 (8)C26—C25—C690.50 (8)
C4—C5—H5109.2C24—C25—H25109.3
C6—C5—H5109.2C26—C25—H25109.3
C26—C5—H5109.2C6—C25—H25109.3
N1—C6—C16111.63 (10)N21—C26—C36111.87 (10)
N1—C6—C5110.78 (9)N21—C26—C25110.58 (9)
C16—C6—C5116.30 (10)C36—C26—C25116.10 (10)
N1—C6—C25113.15 (9)N21—C26—C5113.12 (10)
C16—C6—C25115.67 (10)C36—C26—C5115.63 (10)
C5—C6—C2587.25 (8)C25—C26—C587.42 (8)
N1—C11—H11A109.5N21—C31—H31A109.5
N1—C11—H11B109.5N21—C31—H31B109.5
H11A—C11—H11B109.5H31A—C31—H31B109.5
N1—C11—H11C109.5N21—C31—H31C109.5
H11A—C11—H11C109.5H31A—C31—H31C109.5
H11B—C11—H11C109.5H31B—C31—H31C109.5
N3—C13—H13A109.5N23—C33—H33A109.5
N3—C13—H13B109.5N23—C33—H33B109.5
H13A—C13—H13B109.5H33A—C33—H33B109.5
N3—C13—H13C109.5N23—C33—H33C109.5
H13A—C13—H13C109.5H33A—C33—H33C109.5
H13B—C13—H13C109.5H33B—C33—H33C109.5
C6—C16—H16A109.5C26—C36—H36A109.5
C6—C16—H16B109.5C26—C36—H36B109.5
H16A—C16—H16B109.5H36A—C36—H36B109.5
C6—C16—H16C109.5C26—C36—H36C109.5
H16A—C16—H16C109.5H36A—C36—H36C109.5
H16B—C16—H16C109.5H36B—C36—H36C109.5
C6—N1—C2—O12174.96 (11)O32—C22—N23—C331.28 (17)
C11—N1—C2—O125.84 (17)N21—C22—N23—C33178.82 (11)
C6—N1—C2—N34.36 (17)C22—N23—C24—O34176.44 (11)
C11—N1—C2—N3173.49 (10)C33—N23—C24—O344.56 (17)
O12—C2—N3—C4178.04 (12)C22—N23—C24—C256.99 (17)
N1—C2—N3—C41.30 (18)C33—N23—C24—C25172.01 (10)
O12—C2—N3—C130.24 (16)O34—C24—C25—C26163.54 (11)
N1—C2—N3—C13179.58 (11)N23—C24—C25—C2619.92 (15)
C2—N3—C4—O14172.19 (14)O34—C24—C25—C688.63 (14)
C13—N3—C4—O146.1 (2)N23—C24—C25—C687.92 (13)
C2—N3—C4—C511.26 (18)N1—C6—C25—C2428.35 (14)
C13—N3—C4—C5170.50 (11)C16—C6—C25—C24102.22 (12)
O14—C4—C5—C6159.71 (14)C5—C6—C25—C24139.80 (10)
N3—C4—C5—C623.75 (17)N1—C6—C25—C2695.50 (10)
O14—C4—C5—C2692.17 (17)C16—C6—C25—C26133.93 (10)
N3—C4—C5—C2684.38 (14)C5—C6—C25—C2615.96 (8)
C2—N1—C6—C16115.52 (12)C22—N21—C26—C36112.36 (13)
C11—N1—C6—C1653.41 (14)C31—N21—C26—C3655.07 (15)
C2—N1—C6—C515.81 (15)C22—N21—C26—C2518.72 (16)
C11—N1—C6—C5175.26 (10)C31—N21—C26—C25173.84 (11)
C2—N1—C6—C25111.92 (12)C22—N21—C26—C5114.93 (13)
C11—N1—C6—C2579.15 (12)C31—N21—C26—C577.64 (14)
C4—C5—C6—N125.08 (14)C24—C25—C26—N2124.46 (14)
C26—C5—C6—N198.19 (10)C6—C25—C26—N2198.16 (10)
C4—C5—C6—C16103.78 (13)C24—C25—C26—C36104.38 (12)
C26—C5—C6—C16132.96 (10)C6—C25—C26—C36133.00 (10)
C4—C5—C6—C25138.83 (11)C24—C25—C26—C5138.22 (10)
C26—C5—C6—C2515.57 (8)C6—C25—C26—C515.60 (8)
C26—N21—C22—O32172.70 (12)C4—C5—C26—N2128.56 (13)
C31—N21—C22—O324.95 (18)C6—C5—C26—N2195.34 (10)
C26—N21—C22—N237.20 (18)C4—C5—C26—C36102.30 (13)
C31—N21—C22—N23174.95 (11)C6—C5—C26—C36133.81 (11)
O32—C22—N23—C24179.73 (12)C4—C5—C26—C25139.87 (10)
N21—C22—N23—C240.17 (17)C6—C5—C26—C2515.97 (8)
 

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