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In the title compound, C6H6N2O4, the planar carboxyl group makes a dihedral angle of 74.61 (2)° with the uracil plane. In the crystal structure, inter­molecular N—H...O and O—H...O hydrogen bonds link the mol­ecules into a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022774/cv6542sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022774/cv6542Isup2.hkl
Contains datablock I

CCDC reference: 282306

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.066
  • wR factor = 0.148
  • Data-to-parameter ratio = 8.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10 PLAT731_ALERT_1_C Bond Calc 0.83(6), Rep 0.82(2) ...... 3.00 su-Rat O4 -H4 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(7), Rep 0.84(2) ...... 3.50 su-Rat N2 -H2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.83(6), Rep 0.82(2) ...... 3.00 su-Rat O4 -H4 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(7), Rep 0.84(2) ...... 3.50 su-Rat N2 -H2 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 2.00(7), Rep 2.00(3) ...... 2.33 su-Rat H2 -O3 1.555 2.564
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 25.24 From the CIF: _reflns_number_total 621 Count of symmetry unique reflns 621 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 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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, 2002); software used to prepare material for publication: SHELXL97.

1-(Carboxymethyl)uracil top
Crystal data top
C6H6N2O4F(000) = 176
Mr = 170.13Dx = 1.669 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 861 reflections
a = 5.0999 (8) Åθ = 2.8–24.8°
b = 4.6273 (8) ŵ = 0.14 mm1
c = 15.0106 (19) ÅT = 298 K
β = 107.093 (5)°Rod, colourless
V = 338.58 (9) Å30.21 × 0.11 × 0.10 mm
Z = 2
Data collection top
Bruker APEX area-detector
diffractometer
621 independent reflections
Radiation source: fine-focus sealed tube607 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 25.2°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 66
Tmin = 0.971, Tmax = 0.983k = 55
3071 measured reflectionsl = 1718
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.27 w = 1/[σ2(Fo2) + (0.0727P)2 + 0.2892P]
where P = (Fo2 + 2Fc2)/3
621 reflections(Δ/σ)max < 0.001
75 parametersΔρmax = 0.30 e Å3
4 restraintsΔρmin = 0.31 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
O10.9156 (10)0.3732 (10)0.5139 (3)0.0398 (13)
O20.4403 (10)0.9587 (11)0.2833 (3)0.0396 (13)
O30.9652 (10)0.5312 (11)0.7798 (3)0.0373 (12)
O40.9946 (9)0.8467 (10)0.6727 (3)0.0341 (12)
N10.5691 (10)0.6351 (11)0.5402 (3)0.0252 (12)
N20.6688 (11)0.6708 (13)0.3997 (4)0.0292 (13)
C10.7309 (12)0.5479 (13)0.4864 (4)0.0246 (14)
C20.4686 (13)0.8753 (13)0.3631 (5)0.0275 (14)
C30.3159 (13)0.9613 (16)0.4239 (5)0.0297 (15)
H30.17901.10030.40510.036*
C40.3702 (12)0.8410 (14)0.5085 (5)0.0292 (15)
H4A0.26850.89980.54760.035*
C50.6290 (14)0.5115 (14)0.6334 (4)0.0306 (15)
H5A0.65220.30440.62900.037*
H5B0.47200.54300.65620.037*
C60.8787 (12)0.6316 (13)0.7031 (4)0.0231 (13)
H20.741 (14)0.593 (14)0.362 (4)0.028*
H41.139 (9)0.873 (15)0.715 (4)0.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.039 (3)0.037 (3)0.041 (3)0.013 (2)0.009 (2)0.007 (2)
O20.043 (3)0.048 (3)0.030 (2)0.015 (3)0.014 (2)0.015 (3)
O30.042 (3)0.041 (3)0.028 (2)0.009 (2)0.0091 (19)0.013 (2)
O40.040 (3)0.032 (2)0.027 (2)0.015 (2)0.006 (2)0.003 (2)
N10.026 (3)0.023 (3)0.027 (3)0.001 (2)0.008 (2)0.001 (2)
N20.034 (3)0.036 (3)0.020 (3)0.008 (3)0.012 (2)0.003 (2)
C10.019 (3)0.017 (3)0.031 (3)0.001 (3)0.002 (2)0.009 (3)
C20.027 (3)0.021 (3)0.033 (4)0.001 (3)0.006 (3)0.002 (3)
C30.026 (3)0.026 (3)0.038 (4)0.002 (3)0.011 (3)0.000 (3)
C40.027 (4)0.029 (3)0.035 (3)0.010 (3)0.015 (3)0.008 (3)
C50.039 (4)0.022 (3)0.032 (3)0.003 (3)0.012 (3)0.004 (3)
C60.032 (3)0.017 (3)0.027 (3)0.003 (3)0.019 (3)0.007 (3)
Geometric parameters (Å, º) top
O1—C11.217 (7)N2—C21.382 (8)
O2—C21.227 (8)N2—H20.84 (2)
O3—C61.199 (7)C2—C31.419 (10)
O4—C61.306 (7)C3—C41.339 (10)
O4—H40.82 (2)C3—H30.9300
N1—C41.371 (8)C4—H4A0.9300
N1—C11.374 (8)C5—C61.497 (10)
N1—C51.459 (8)C5—H5A0.9700
N2—C11.369 (9)C5—H5B0.9700
C6—O4—H4104 (5)C4—C3—H3120.2
C4—N1—C1120.8 (5)C2—C3—H3120.2
C4—N1—C5122.0 (5)C3—C4—N1122.9 (6)
C1—N1—C5117.1 (5)C3—C4—H4A118.6
C1—N2—C2126.9 (5)N1—C4—H4A118.6
C1—N2—H2116 (5)N1—C5—C6114.9 (5)
C2—N2—H2116 (5)N1—C5—H5A108.6
O1—C1—N2122.6 (6)C6—C5—H5A108.6
O1—C1—N1122.3 (6)N1—C5—H5B108.6
N2—C1—N1115.1 (5)C6—C5—H5B108.6
O2—C2—N2117.7 (6)H5A—C5—H5B107.5
O2—C2—C3127.6 (6)O3—C6—O4123.6 (6)
N2—C2—C3114.7 (6)O3—C6—C5121.7 (6)
C4—C3—C2119.6 (6)O4—C6—C5114.7 (5)
C2—N2—C1—O1178.3 (6)N2—C2—C3—C41.0 (9)
C2—N2—C1—N11.9 (9)C2—C3—C4—N10.1 (10)
C4—N1—C1—O1177.3 (6)C1—N1—C4—C32.1 (9)
C5—N1—C1—O10.7 (9)C5—N1—C4—C3178.6 (6)
C4—N1—C1—N22.9 (8)C4—N1—C5—C6101.4 (7)
C5—N1—C1—N2179.5 (5)C1—N1—C5—C675.2 (7)
C1—N2—C2—O2179.2 (7)N1—C5—C6—O3173.2 (5)
C1—N2—C2—C30.0 (9)N1—C5—C6—O45.4 (8)
O2—C2—C3—C4178.1 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O2i0.82 (2)1.76 (3)2.553 (7)160 (7)
N2—H2···O3ii0.84 (2)2.00 (3)2.828 (7)169 (7)
Symmetry codes: (i) x+1, y+2, z+1/2; (ii) x, y+1, z1/2.
 

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