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The crystal structure of the title compound, C7H8N2O3, contains a 1:1 mixture of two tautomers, viz. ethyl 6-oxo-1,6-dihydro­pyrimidine-5-carboxyl­ate and ethyl 4-oxo-1,4-dihydro­pyrimidine-5-carboxyl­ate. The mol­ecules are linked into a three-dimensional network by N—H...O, C—H...O and C—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045995/wn2076sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045995/wn2076Isup2.hkl
Contains datablock I

CCDC reference: 630499

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.053
  • wR factor = 0.118
  • Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.97 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.69 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.18 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C6 - C7 ... 1.41 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 1526 Count of symmetry unique reflns 1526 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

ethyl 6-oxo-1,6-dihydropyrimidine-5-carboxylate–ethyl 4-oxo-1,4-dihydropyrimidine-5-carboxylate (1/1) top
Crystal data top
C7H8N2O3F(000) = 704
Mr = 168.15Dx = 1.441 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1061 reflections
a = 4.768 (3) Åθ = 2.3–20.2°
b = 25.590 (16) ŵ = 0.12 mm1
c = 12.821 (8) ÅT = 292 K
β = 97.687 (10)°Plate, colorless
V = 1550.4 (17) Å30.40 × 0.10 × 0.03 mm
Z = 8
Data collection top
Bruker SMART APEX CCD
diffractometer
1121 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
Graphite monochromatorθmax = 26.0°, θmin = 1.6°
φ and ω scansh = 55
4986 measured reflectionsk = 2931
1526 independent reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0587P)2]
where P = (Fo2 + 2Fc2)/3
1526 reflections(Δ/σ)max < 0.001
219 parametersΔρmax = 0.25 e Å3
4 restraintsΔρmin = 0.17 e Å3
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
C10.5020 (10)0.10368 (18)0.5261 (4)0.0447 (11)
C20.6793 (9)0.14479 (16)0.4943 (3)0.0404 (11)
C30.8987 (12)0.1440 (2)0.6751 (4)0.0548 (14)
H31.03410.15900.72520.066*
C40.5475 (12)0.0869 (2)0.6282 (4)0.0589 (14)
H40.43190.06010.64680.071*
C50.2728 (11)0.0773 (2)0.4559 (5)0.0589 (14)
C60.0149 (16)0.0703 (3)0.2828 (6)0.090 (2)
H6A0.13790.05960.32100.108*
H6B0.05960.09560.22980.108*
C70.1191 (17)0.0266 (3)0.2338 (6)0.108 (3)
H7A0.25810.03770.19080.162*
H7B0.03390.00950.19060.162*
H7C0.20420.00270.28650.162*
C80.6203 (10)0.29602 (18)0.6021 (3)0.0382 (10)
C90.4030 (9)0.25740 (18)0.6016 (3)0.0383 (11)
C100.5240 (11)0.2486 (2)0.7818 (4)0.0479 (12)
H100.49210.23360.84520.057*
C110.7818 (10)0.30764 (18)0.6961 (3)0.0429 (11)
H110.92490.33250.69850.051*
C120.6773 (10)0.32283 (17)0.5031 (3)0.0434 (11)
C130.9330 (14)0.3913 (2)0.4335 (4)0.0693 (17)
H13A0.76440.40470.39130.083*
H13B1.02900.36820.38990.083*
C141.1210 (16)0.4348 (2)0.4721 (5)0.084 (2)
H14A1.02200.45830.51280.126*
H14B1.17880.45320.41330.126*
H14C1.28490.42130.51530.126*
N10.8717 (8)0.16304 (14)0.5768 (3)0.0426 (9)
H10.96730.18950.56020.051*
N20.7456 (11)0.10560 (18)0.7047 (3)0.0646 (12)
N30.3623 (9)0.23451 (16)0.6977 (3)0.0497 (11)
N40.7330 (8)0.28318 (16)0.7841 (3)0.0474 (10)
H4A0.85660.29030.83770.057*
O10.6751 (6)0.16546 (13)0.4074 (2)0.0520 (9)
O20.1230 (10)0.04496 (17)0.4861 (4)0.0884 (14)
O30.2429 (9)0.09459 (17)0.3562 (3)0.0785 (13)
O40.2451 (7)0.24239 (13)0.5226 (2)0.0558 (10)
O50.5775 (9)0.31038 (14)0.4162 (2)0.0647 (10)
O60.8548 (8)0.36256 (14)0.5243 (2)0.0561 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.038 (3)0.051 (3)0.046 (3)0.000 (2)0.008 (2)0.001 (2)
C20.040 (3)0.044 (3)0.035 (2)0.006 (2)0.000 (2)0.002 (2)
C30.058 (3)0.069 (4)0.037 (3)0.005 (3)0.002 (2)0.000 (2)
C40.062 (4)0.053 (3)0.064 (4)0.006 (3)0.017 (3)0.011 (3)
C50.043 (3)0.061 (3)0.075 (4)0.004 (3)0.013 (3)0.013 (3)
C60.089 (5)0.080 (5)0.092 (5)0.024 (4)0.017 (4)0.018 (4)
C70.121 (7)0.084 (5)0.108 (5)0.010 (5)0.022 (5)0.028 (4)
C80.041 (3)0.046 (3)0.027 (2)0.001 (2)0.0014 (18)0.0050 (18)
C90.038 (3)0.048 (3)0.026 (2)0.006 (2)0.0062 (19)0.0002 (19)
C100.051 (3)0.063 (3)0.030 (2)0.002 (3)0.004 (2)0.001 (2)
C110.041 (3)0.053 (3)0.033 (2)0.001 (2)0.0009 (19)0.007 (2)
C120.045 (3)0.048 (3)0.036 (3)0.006 (2)0.001 (2)0.000 (2)
C130.090 (5)0.066 (4)0.054 (3)0.006 (3)0.016 (3)0.012 (3)
C140.105 (6)0.074 (4)0.074 (4)0.026 (4)0.015 (4)0.000 (3)
N10.047 (3)0.048 (2)0.0309 (19)0.0016 (19)0.0011 (16)0.0016 (17)
N20.071 (3)0.074 (3)0.048 (2)0.014 (3)0.007 (2)0.012 (2)
N30.052 (3)0.067 (3)0.0296 (19)0.006 (2)0.0030 (18)0.0010 (17)
N40.043 (2)0.071 (3)0.0261 (18)0.001 (2)0.0051 (16)0.0038 (18)
O10.046 (2)0.068 (2)0.0394 (18)0.0001 (17)0.0026 (16)0.0100 (16)
O20.078 (3)0.092 (3)0.095 (3)0.041 (3)0.012 (2)0.006 (3)
O30.069 (3)0.096 (3)0.065 (3)0.025 (2)0.011 (2)0.008 (2)
O40.062 (2)0.073 (2)0.0284 (16)0.0162 (18)0.0102 (15)0.0012 (15)
O50.082 (3)0.084 (2)0.0270 (17)0.023 (2)0.0030 (16)0.0005 (17)
O60.070 (2)0.059 (2)0.0385 (16)0.0171 (19)0.0055 (17)0.0006 (16)
Geometric parameters (Å, º) top
C1—C41.366 (7)C8—C91.431 (6)
C1—C21.442 (6)C8—C121.500 (6)
C1—C51.483 (7)C9—O41.239 (5)
C2—O11.230 (5)C9—N31.402 (6)
C2—N11.385 (5)C10—N31.290 (6)
C3—N21.310 (7)C10—N41.329 (6)
C3—N11.341 (6)C10—H100.9300
C3—H30.9300C11—N41.338 (6)
C4—N21.355 (7)C11—H110.9300
C4—H40.9300C12—O51.195 (5)
C5—O21.190 (6)C12—O61.328 (6)
C5—O31.343 (7)C13—O61.467 (6)
C6—C71.406 (9)C13—C141.473 (8)
C6—O31.476 (7)C13—H13A0.9700
C6—H6A0.9700C13—H13B0.9700
C6—H6B0.9700C14—H14A0.9600
C7—H7A0.9600C14—H14B0.9600
C7—H7B0.9600C14—H14C0.9600
C7—H7C0.9600N1—H10.8595
C8—C111.373 (6)N4—H4A0.8626
C4—C1—C2118.5 (4)N3—C9—C8118.0 (4)
C4—C1—C5116.6 (5)N3—C10—N4124.6 (4)
C2—C1—C5124.9 (4)N3—C10—H10117.7
O1—C2—N1118.3 (4)N4—C10—H10117.7
O1—C2—C1129.1 (4)N4—C11—C8119.9 (5)
N1—C2—C1112.5 (4)N4—C11—H11120.0
N2—C3—N1123.8 (5)C8—C11—H11120.0
N2—C3—H3118.1O5—C12—O6124.0 (4)
N1—C3—H3118.1O5—C12—C8125.0 (4)
N2—C4—C1126.0 (5)O6—C12—C8111.0 (4)
N2—C4—H4117.0O6—C13—C14108.7 (5)
C1—C4—H4117.0O6—C13—H13A110.0
O2—C5—O3123.2 (5)C14—C13—H13A110.0
O2—C5—C1123.0 (5)O6—C13—H13B110.0
O3—C5—C1113.8 (5)C14—C13—H13B110.0
C7—C6—O3110.2 (6)H13A—C13—H13B108.3
C7—C6—H6A109.6C13—C14—H14A109.5
O3—C6—H6A109.6C13—C14—H14B109.5
C7—C6—H6B109.6H14A—C14—H14B109.5
O3—C6—H6B109.6C13—C14—H14C109.5
H6A—C6—H6B108.1H14A—C14—H14C109.5
C6—C7—H7A109.5H14B—C14—H14C109.5
C6—C7—H7B109.5C3—N1—C2124.5 (4)
H7A—C7—H7B109.5C3—N1—H1122.1
C6—C7—H7C109.5C2—N1—H1113.3
H7A—C7—H7C109.5C3—N2—C4114.7 (4)
H7B—C7—H7C109.5C10—N3—C9118.7 (4)
C11—C8—C9118.3 (4)C10—N4—C11120.4 (4)
C11—C8—C12120.0 (4)C10—N4—H4A126.1
C9—C8—C12121.6 (4)C11—N4—H4A113.3
O4—C9—N3116.7 (4)C5—O3—C6116.3 (5)
O4—C9—C8125.3 (4)C12—O6—C13116.3 (4)
C4—C1—C2—O1179.9 (5)C11—C8—C12—O611.1 (6)
C5—C1—C2—O10.7 (7)C9—C8—C12—O6170.1 (4)
C4—C1—C2—N12.1 (6)N2—C3—N1—C20.2 (7)
C5—C1—C2—N1178.7 (4)O1—C2—N1—C3179.9 (5)
C2—C1—C4—N20.6 (8)C1—C2—N1—C31.9 (6)
C5—C1—C4—N2179.8 (5)N1—C3—N2—C41.9 (8)
C4—C1—C5—O24.0 (7)C1—C4—N2—C31.5 (8)
C2—C1—C5—O2176.8 (5)N4—C10—N3—C91.2 (8)
C4—C1—C5—O3178.5 (5)O4—C9—N3—C10179.3 (4)
C2—C1—C5—O30.7 (7)C8—C9—N3—C100.9 (6)
C11—C8—C9—O4178.7 (5)N3—C10—N4—C112.6 (8)
C12—C8—C9—O40.2 (7)C8—C11—N4—C101.8 (7)
C11—C8—C9—N31.6 (6)O2—C5—O3—C61.6 (8)
C12—C8—C9—N3179.5 (4)C1—C5—O3—C6179.1 (5)
C9—C8—C11—N40.3 (7)C7—C6—O3—C590.7 (8)
C12—C8—C11—N4179.1 (4)O5—C12—O6—C131.4 (7)
C11—C8—C12—O5168.8 (5)C8—C12—O6—C13178.6 (4)
C9—C8—C12—O510.0 (7)C14—C13—O6—C12177.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.862.002.847 (5)170
C3—H3···N3i0.932.543.188 (7)127
N4—H4A···O1ii0.862.012.789 (5)151
C3—H3···O5ii0.932.553.307 (6)139
C10—H10···O4ii0.932.503.135 (6)125
C10—H10···O5iii0.932.553.281 (7)136
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y+1/2, z+1/2; (iii) x1/2, y+1/2, z+1/2.
 

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