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The title compound, 4-amino-5-fluoro-2-hydroxy­pyrimidine monohydrate, C4H4FN3O·H2O, with two mol­ecules of each comprising the asymmetric unit, has been redetermined, providing a significant increase in the precision of the geometric parameters.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680600496X/tk2002sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680600496X/tk2002Isup2.hkl
Contains datablock I

CCDC reference: 601253

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.055
  • wR factor = 0.165
  • Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96
Alert level C PLAT417_ALERT_2_C Short Inter D-H..H-D H9 .. H12 .. 2.13 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C4 H4 F N3 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 H2 O
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 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 1 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 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XCS (Colapietro et al., 1992); cell refinement: XCS; data reduction: XCS; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

5-fluorocytosine monohydrate top
Crystal data top
C4H4FN3O·H2OF(000) = 608
Mr = 147.12Dx = 1.580 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.710689 Å
Hall symbol: -P 2ybcCell parameters from 15 reflections
a = 7.5142 (11) Åθ = 15–21°
b = 9.4241 (16) ŵ = 0.15 mm1
c = 17.692 (6) ÅT = 298 K
β = 99.16 (2)°Block, colourless
V = 1236.9 (5) Å30.30 × 0.20 × 0.20 mm
Z = 8
Data collection top
Huber CS four-circle
diffractometer
Rint = 0.018
Radiation source: X-Ray tubeθmax = 30.0°, θmin = 3.5°
Graphite monochromatorh = 010
ω scansk = 013
6074 measured reflectionsl = 2424
3447 independent reflections3 standard reflections every 97 reflections
2944 reflections with I > 2σ(I) intensity decay: 3%
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.165H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0976P)2 + 0.1585P]
where P = (Fo2 + 2Fc2)/3
3447 reflections(Δ/σ)max = 0.001
193 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.20 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
F10.10327 (12)0.06003 (9)0.55725 (5)0.0645 (3)
O10.33592 (13)0.07351 (8)0.82445 (5)0.0496 (2)
N10.17626 (14)0.05515 (9)0.72849 (6)0.0423 (2)
N20.17917 (13)0.19482 (8)0.72440 (5)0.0389 (2)
N30.01815 (14)0.31223 (10)0.62157 (6)0.0492 (3)
C10.23321 (15)0.07214 (10)0.76147 (6)0.0383 (2)
C20.06963 (14)0.19143 (11)0.65736 (6)0.0384 (2)
C30.00890 (15)0.05872 (12)0.62435 (6)0.0428 (3)
C40.06507 (16)0.06243 (11)0.66026 (7)0.0454 (3)
F20.63434 (12)0.43341 (8)0.96069 (5)0.0598 (2)
O20.18395 (13)0.43056 (8)0.69612 (5)0.0481 (2)
N40.35357 (13)0.55537 (9)0.79080 (6)0.0423 (2)
N50.34467 (12)0.30510 (9)0.79371 (5)0.0389 (2)
N60.50679 (15)0.18376 (10)0.89463 (6)0.0510 (3)
C50.29114 (14)0.42899 (10)0.75768 (6)0.0379 (2)
C60.45679 (14)0.30582 (11)0.86030 (6)0.0385 (2)
C70.52119 (15)0.43769 (11)0.89367 (6)0.0419 (2)
C80.46677 (16)0.56017 (11)0.85900 (7)0.0442 (3)
O30.77082 (19)0.11555 (15)1.03418 (6)0.0780 (4)
O40.1703 (2)0.36031 (14)0.45546 (7)0.0931 (5)
H10.22680.12930.75390.062 (4)*
H20.06020.39570.64370.061 (4)*
H30.05290.30470.57920.077 (5)*
H40.03310.15130.63980.066 (4)*
H50.30370.63520.76670.061 (4)*
H60.45870.10100.87270.066 (4)*
H70.58050.18540.93780.078 (5)*
H80.50480.64970.88110.064 (4)*
H90.87660.12891.03640.145 (12)*
H100.74200.11111.08040.076 (5)*
H110.20880.36780.40690.087 (6)*
H120.22180.43810.48010.132 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0631 (5)0.0673 (5)0.0540 (5)0.0005 (4)0.0186 (4)0.0112 (3)
O10.0652 (5)0.0419 (4)0.0379 (4)0.0025 (3)0.0030 (4)0.0010 (3)
N10.0505 (5)0.0315 (4)0.0439 (5)0.0000 (3)0.0051 (4)0.0007 (3)
N20.0472 (5)0.0321 (4)0.0360 (4)0.0015 (3)0.0030 (3)0.0005 (3)
N30.0557 (6)0.0437 (5)0.0446 (5)0.0007 (4)0.0029 (4)0.0061 (4)
C10.0461 (5)0.0340 (5)0.0352 (5)0.0006 (4)0.0075 (4)0.0002 (3)
C20.0390 (5)0.0394 (5)0.0369 (5)0.0007 (4)0.0059 (4)0.0004 (3)
C30.0415 (5)0.0448 (5)0.0399 (5)0.0016 (4)0.0004 (4)0.0059 (4)
C40.0470 (6)0.0378 (5)0.0506 (6)0.0034 (4)0.0056 (5)0.0097 (4)
F20.0617 (5)0.0642 (5)0.0467 (4)0.0020 (3)0.0128 (3)0.0085 (3)
O20.0568 (5)0.0415 (4)0.0420 (4)0.0019 (3)0.0047 (4)0.0002 (3)
N40.0477 (5)0.0328 (4)0.0450 (5)0.0010 (3)0.0029 (4)0.0016 (3)
N50.0436 (4)0.0331 (4)0.0383 (4)0.0013 (3)0.0010 (3)0.0004 (3)
N60.0585 (6)0.0436 (5)0.0464 (5)0.0008 (4)0.0051 (4)0.0055 (4)
C50.0408 (5)0.0340 (5)0.0382 (5)0.0005 (3)0.0046 (4)0.0009 (3)
C60.0390 (5)0.0389 (5)0.0371 (5)0.0004 (3)0.0045 (4)0.0002 (3)
C70.0416 (5)0.0454 (5)0.0373 (5)0.0030 (4)0.0014 (4)0.0058 (4)
C80.0458 (6)0.0387 (5)0.0471 (6)0.0044 (4)0.0044 (5)0.0087 (4)
O30.0870 (9)0.1027 (9)0.0432 (5)0.0077 (7)0.0071 (5)0.0108 (5)
O40.1332 (13)0.0871 (8)0.0557 (6)0.0333 (8)0.0049 (7)0.0182 (6)
Geometric parameters (Å, º) top
F1—C31.3421 (13)N4—C81.3619 (15)
O1—C11.2504 (14)N4—C51.3763 (13)
N1—C41.3562 (15)N4—H50.9152
N1—C11.3722 (13)N5—C61.3349 (13)
N1—H10.8830N5—C51.3601 (13)
N2—C21.3322 (13)N6—C61.3269 (14)
N2—C11.3591 (13)N6—H60.9194
N3—C21.3299 (14)N6—H70.8700
N3—H20.9128C6—C71.4270 (14)
N3—H30.8513C7—C81.3401 (16)
C2—C31.4243 (14)C8—H80.9540
C3—C41.3417 (16)O3—H90.7993
C4—H40.9285O3—H100.8791
F2—C71.3452 (13)O4—H110.8647
O2—C51.2474 (13)O4—H120.9645
C4—N1—C1121.94 (9)C8—N4—H5122.5
C4—N1—H1124.5C5—N4—H5115.3
C1—N1—H1113.3C6—N5—C5120.48 (8)
C2—N2—C1120.27 (8)C6—N6—H6118.6
C2—N3—H2118.6C6—N6—H7118.7
C2—N3—H3116.3H6—N6—H7122.6
H2—N3—H3125.1O2—C5—N5121.41 (9)
O1—C1—N2121.05 (9)O2—C5—N4119.37 (9)
O1—C1—N1119.63 (9)N5—C5—N4119.21 (9)
N2—C1—N1119.31 (10)N6—C6—N5119.50 (9)
N3—C2—N2119.68 (9)N6—C6—C7120.87 (10)
N3—C2—C3120.43 (10)N5—C6—C7119.63 (9)
N2—C2—C3119.90 (9)C8—C7—F2122.23 (9)
C4—C3—F1122.19 (10)C8—C7—C6120.14 (10)
C4—C3—C2119.80 (10)F2—C7—C6117.62 (9)
F1—C3—C2118.02 (10)C7—C8—N4118.62 (9)
C3—C4—N1118.77 (9)C7—C8—H8121.6
C3—C4—H4122.7N4—C8—H8119.8
N1—C4—H4118.5H9—O3—H10110.6
C8—N4—C5121.90 (9)H11—O4—H12107.0
C2—N2—C1—O1179.97 (9)C6—N5—C5—O2178.71 (9)
C2—N2—C1—N11.11 (15)C6—N5—C5—N40.18 (15)
C4—N1—C1—O1179.92 (10)C8—N4—C5—O2178.14 (10)
C4—N1—C1—N20.98 (16)C8—N4—C5—N50.42 (16)
C1—N2—C2—N3179.81 (9)C5—N5—C6—N6179.75 (10)
C1—N2—C2—C30.02 (15)C5—N5—C6—C70.20 (15)
N3—C2—C3—C4178.53 (11)N6—C6—C7—C8178.74 (11)
N2—C2—C3—C41.26 (16)N5—C6—C7—C81.21 (16)
N3—C2—C3—F11.10 (16)N6—C6—C7—F20.24 (16)
N2—C2—C3—F1179.11 (9)N5—C6—C7—F2179.81 (9)
F1—C3—C4—N1179.00 (10)F2—C7—C8—N4179.30 (9)
C2—C3—C4—N11.39 (17)C6—C7—C8—N41.76 (17)
C1—N1—C4—C30.29 (17)C5—N4—C8—C71.40 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N50.881.962.8313 (13)171
N3—H2···O2i0.912.032.9402 (14)173
N3—H3···O40.852.293.0858 (18)156
N4—H5···N2ii0.921.942.8548 (13)173
N6—H6···O10.922.012.9260 (14)176
N6—H7···O30.872.152.9810 (18)161
O3—H9···O4iii0.802.192.987 (2)174
O3—H10···O1iv0.881.902.7739 (16)171
O4—H11···O2v0.861.952.7483 (17)152
O4—H12···O3vi0.961.932.8492 (19)158
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x+1, y1/2, z+3/2; (iv) x+1, y, z+2; (v) x, y, z+1; (vi) x1, y+1/2, z1/2.
 

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