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In the title compound, C7H7FN2O4, the propionic acid group is twisted out of the pyrimidine plane. In the crystal structure, mol­ecules are connected by inter­molecular N—H...O and O—H...O hydrogen bonds, forming columns.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000584/is6171sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000584/is6171Isup2.hkl
Contains datablock I

CCDC reference: 298473

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.047
  • wR factor = 0.145
  • Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O2 - C1 .. 12.08 su
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.08
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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, 1997); cell refinement: SAINT (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL.

5-Fluorouracil-1-propionic acid top
Crystal data top
C7H7FN2O4Dx = 1.577 Mg m3
Mr = 202.15Melting point: 457 K
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 20.279 (6) ÅCell parameters from 1663 reflections
b = 8.137 (2) Åθ = 2.8–26.3°
c = 13.222 (4) ŵ = 0.14 mm1
β = 128.673 (4)°T = 294 K
V = 1703.3 (8) Å3Block, colourless
Z = 80.26 × 0.24 × 0.20 mm
F(000) = 832
Data collection top
Bruker SMART CCD area-detector
diffractometer
1747 independent reflections
Radiation source: fine-focus sealed tube1245 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 26.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2025
Tmin = 0.958, Tmax = 0.972k = 710
4556 measured reflectionsl = 1616
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0679P)2 + 1.9948P]
where P = (Fo2 + 2Fc2)/3
1747 reflections(Δ/σ)max = 0.002
137 parametersΔρmax = 0.30 e Å3
14 restraintsΔρmin = 0.41 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*/UeqOcc. (<1)
F10.11918 (9)0.74550 (19)0.00859 (18)0.0595 (5)
O10.09860 (12)0.3482 (2)0.23697 (17)0.0488 (5)
O20.16000 (17)0.3696 (3)0.4480 (3)0.0767 (7)
H2C0.130 (4)0.291 (6)0.439 (8)0.092*0.50
H2D0.199 (3)0.411 (10)0.520 (4)0.092*0.50
O30.19940 (10)0.9631 (2)0.30681 (17)0.0455 (5)
O40.08222 (10)1.0748 (2)0.04855 (17)0.0453 (5)
N10.10767 (11)0.7502 (2)0.19657 (18)0.0301 (5)
N20.05845 (12)1.0148 (2)0.18074 (19)0.0315 (5)
H2E0.0676 (17)1.110 (4)0.201 (3)0.042 (8)*
C10.15073 (15)0.4128 (3)0.3432 (2)0.0348 (6)
C20.20949 (14)0.5458 (3)0.3625 (2)0.0391 (6)
H2A0.21850.62430.42520.047*
H2B0.26370.49690.39820.047*
C30.17716 (14)0.6360 (3)0.2399 (2)0.0360 (6)
H3A0.22330.69720.25390.043*
H3B0.15770.55640.17180.043*
C40.12708 (14)0.9128 (3)0.2337 (2)0.0300 (5)
C50.02572 (14)0.9731 (3)0.0961 (2)0.0302 (5)
C60.03845 (14)0.7997 (3)0.0698 (2)0.0345 (6)
C70.02560 (14)0.6967 (3)0.1174 (2)0.0351 (6)
H70.01450.58570.09650.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0270 (8)0.0411 (10)0.0808 (12)0.0065 (6)0.0191 (8)0.0076 (8)
O10.0573 (12)0.0242 (9)0.0482 (11)0.0097 (8)0.0248 (10)0.0057 (8)
O20.0897 (19)0.0610 (16)0.0727 (16)0.0262 (13)0.0475 (15)0.0076 (12)
O30.0294 (9)0.0357 (10)0.0520 (11)0.0084 (8)0.0160 (9)0.0049 (8)
O40.0372 (9)0.0335 (10)0.0549 (11)0.0110 (8)0.0237 (9)0.0002 (8)
N10.0272 (10)0.0199 (9)0.0380 (11)0.0008 (7)0.0177 (9)0.0014 (7)
N20.0337 (11)0.0170 (10)0.0363 (11)0.0019 (8)0.0183 (9)0.0042 (8)
C10.0359 (12)0.0180 (11)0.0408 (14)0.0004 (9)0.0192 (11)0.0016 (10)
C20.0286 (12)0.0267 (13)0.0497 (15)0.0014 (10)0.0184 (11)0.0048 (10)
C30.0315 (12)0.0270 (12)0.0493 (15)0.0048 (10)0.0252 (12)0.0037 (10)
C40.0298 (12)0.0240 (11)0.0324 (12)0.0010 (9)0.0176 (10)0.0013 (9)
C50.0311 (12)0.0267 (12)0.0326 (12)0.0005 (9)0.0197 (10)0.0009 (9)
C60.0250 (11)0.0289 (12)0.0391 (13)0.0033 (9)0.0149 (10)0.0024 (10)
C70.0325 (12)0.0217 (11)0.0424 (14)0.0053 (9)0.0192 (11)0.0030 (10)
Geometric parameters (Å, º) top
F1—C61.352 (3)N2—C51.376 (3)
O1—C11.229 (3)N2—H2E0.81 (3)
O2—C11.324 (3)C1—C21.509 (3)
O2—H2C0.839 (10)C2—C31.506 (3)
O2—H2D0.839 (10)C2—H2A0.9700
O3—C41.217 (3)C2—H2B0.9700
O4—C51.222 (3)C3—H3A0.9700
N1—C31.473 (3)C3—H3B0.9700
N1—C41.380 (3)C5—C61.437 (3)
N1—C71.370 (3)C6—C71.328 (3)
N2—C41.377 (3)C7—H70.9300
C1—O2—H2C116 (6)N1—C3—C2113.14 (19)
C1—O2—H2D119 (6)N1—C3—H3A109.0
H2C—O2—H2D124 (8)C2—C3—H3A109.0
C7—N1—C4121.10 (19)N1—C3—H3B109.0
C7—N1—C3120.44 (18)C2—C3—H3B109.0
C4—N1—C3118.42 (18)H3A—C3—H3B107.8
C5—N2—C4127.6 (2)O3—C4—N2122.3 (2)
C5—N2—H2E114.8 (19)O3—C4—N1122.6 (2)
C4—N2—H2E118 (2)N2—C4—N1115.05 (19)
O1—C1—O2122.7 (2)O4—C5—N2122.6 (2)
O1—C1—C2121.6 (2)O4—C5—C6124.9 (2)
O2—C1—C2115.7 (2)N2—C5—C6112.51 (19)
C3—C2—C1113.6 (2)C7—C6—F1121.0 (2)
C3—C2—H2A108.8C7—C6—C5122.0 (2)
C1—C2—H2A108.8F1—C6—C5117.01 (19)
C3—C2—H2B108.8C6—C7—N1121.5 (2)
C1—C2—H2B108.8C6—C7—H7119.2
H2A—C2—H2B107.7N1—C7—H7119.2
O1—C1—C2—C323.2 (3)C4—N2—C5—O4175.6 (2)
O2—C1—C2—C3157.7 (2)C4—N2—C5—C63.5 (3)
C7—N1—C3—C288.0 (3)O4—C5—C6—C7175.1 (2)
C4—N1—C3—C294.4 (2)N2—C5—C6—C73.9 (3)
C1—C2—C3—N173.9 (3)O4—C5—C6—F13.4 (4)
C5—N2—C4—O3179.1 (2)N2—C5—C6—F1177.6 (2)
C5—N2—C4—N10.3 (3)F1—C6—C7—N1179.8 (2)
C7—N1—C4—O3177.8 (2)C5—C6—C7—N11.3 (4)
C3—N1—C4—O34.6 (3)C4—N1—C7—C62.3 (3)
C7—N1—C4—N22.8 (3)C3—N1—C7—C6175.2 (2)
C3—N1—C4—N2174.80 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2E···O1i0.81 (3)2.00 (3)2.797 (3)171 (3)
O2—H2C···O4ii0.84 (1)2.06 (2)2.887 (3)167 (8)
O2—H2D···O3iii0.84 (1)2.15 (1)2.990 (3)174 (8)
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z+1/2; (iii) x+1/2, y+3/2, z+1.
 

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