5-Fluoro-1-(penta-noyl)pyrimidine-2,4(1H,3H)-dione.

The penta-noyl group and the 5-fluoro-uracil moiety of the title compound, C(9)H(11)FN(2)O(3), are essentially coplanar, with the penta-noyl carbonyl group oriented towards the ring CH group and away from the nearer ring carbonyl group. In the crystal structure, two inversion-related mol-ecules form a dimer structure, in which two N-H⋯O hydrogen bonds generate an inter-molecular R(2) (2)(8) ring. In addition, there are intra- and inter-molecular C-H⋯O inter-actions.

Related literature

For similar 5-fluoro­pyrimidine-2,4(1H,3H)-dione structures with N1-acyl substituents, see: Beall et al. (1997 ▶); Jiang et al. (1988 ▶); Lehmler & Parkin (2000 ▶). For related literature, see: Roberts & Sloan (1999 ▶).

Experimental

Crystal data

C9H11FN2O3

M = 214.20

Triclinic,

a = 5.3165 (2) Å

b = 9.3986 (4) Å

c = 10.1895 (5) Å

α = 96.000 (3)°

β = 100.957 (3)°

γ = 105.539 (3)°

V = 475.04 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 87.8 (2) K

0.30 × 0.30 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.963, T max = 0.996

12409 measured reflections

2167 independent reflections

1727 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.092

S = 1.02

2167 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and local procedures.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004418/at2544sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004418/at2544Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H11FN2O3	Z = 2
Mr = 214.20	F000 = 224
Triclinic, P1	Dx = 1.497 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.3165 (2) Å	Cell parameters from 6994 reflections
b = 9.3986 (4) Å	θ = 1.0–27.5º
c = 10.1895 (5) Å	µ = 0.13 mm−1
α = 96.000 (3)º	T = 87.8 (2) K
β = 100.957 (3)º	Irregular plate, colourless
γ = 105.539 (3)º	0.30 × 0.30 × 0.03 mm
V = 475.04 (4) Å3

Nonius KappaCCD diffractometer	2167 independent reflections
Radiation source: fine-focus sealed tube	1727 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
Detector resolution: 18 pixels mm-1	θmax = 27.5º
T = 87.8(2) K	θmin = 2.1º
ω scans at fixed χ = 55°	h = −6→6
Absorption correction: multi-scan(SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
Tmin = 0.963, Tmax = 0.996	l = −13→13
12409 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0269P)2 + 0.2309P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2167 reflections	Δρmax = 0.23 e Å−3
137 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2σ(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.

	x	y	z	Uiso*/Ueq
N1	0.4196 (2)	0.37039 (13)	0.62262 (12)	0.0131 (3)
O2	0.7435 (2)	0.24634 (12)	0.65488 (10)	0.0208 (3)
C2	0.6455 (3)	0.33911 (17)	0.69638 (15)	0.0146 (3)
N3	0.7532 (2)	0.42493 (13)	0.82378 (12)	0.0149 (3)
H3	0.8913	0.4049	0.8723	0.018*
O4	0.7890 (2)	0.60838 (12)	0.99779 (10)	0.0176 (3)
C4	0.6725 (3)	0.53737 (16)	0.88432 (15)	0.0148 (3)
F5	0.34305 (17)	0.66618 (10)	0.85412 (8)	0.0198 (2)
C5	0.4391 (3)	0.56025 (16)	0.80080 (15)	0.0142 (3)
C6	0.3224 (3)	0.48168 (16)	0.67833 (14)	0.0135 (3)
H6	0.1698	0.5013	0.6273	0.016*
O7	0.1183 (2)	0.35259 (12)	0.42664 (10)	0.0189 (3)
C7	0.2850 (3)	0.30070 (16)	0.48388 (15)	0.0139 (3)
C8	0.3615 (3)	0.17280 (17)	0.41877 (15)	0.0162 (3)
H8A	0.3494	0.0949	0.4775	0.019*
H8B	0.5500	0.2088	0.4108	0.019*
C9	0.1823 (3)	0.10375 (17)	0.27854 (15)	0.0170 (3)
H9A	0.1644	0.1853	0.2267	0.020*
H9B	0.2710	0.0418	0.2302	0.020*
C10	−0.0962 (3)	0.00735 (17)	0.28048 (16)	0.0192 (4)
H10A	−0.1828	0.0668	0.3330	0.023*
H10B	−0.0809	−0.0788	0.3262	0.023*
C11	−0.2706 (3)	−0.0500 (2)	0.13778 (17)	0.0266 (4)
H11A	−0.2890	0.0351	0.0929	0.040*
H11B	−0.4482	−0.1117	0.1427	0.040*
H11C	−0.1868	−0.1103	0.0860	0.040*

	U11	U22	U33	U12	U13	U23
N1	0.0116 (6)	0.0140 (6)	0.0139 (6)	0.0054 (5)	0.0013 (5)	0.0013 (5)
O2	0.0197 (6)	0.0233 (6)	0.0206 (6)	0.0133 (5)	−0.0006 (5)	−0.0007 (5)
C2	0.0119 (7)	0.0156 (8)	0.0167 (8)	0.0044 (6)	0.0029 (6)	0.0047 (6)
N3	0.0117 (6)	0.0165 (7)	0.0155 (7)	0.0060 (5)	−0.0016 (5)	0.0023 (5)
O4	0.0164 (6)	0.0196 (6)	0.0153 (6)	0.0061 (5)	0.0002 (4)	0.0007 (5)
C4	0.0141 (8)	0.0139 (8)	0.0170 (8)	0.0031 (6)	0.0050 (6)	0.0047 (6)
F5	0.0199 (5)	0.0208 (5)	0.0193 (5)	0.0116 (4)	0.0009 (4)	−0.0027 (4)
C5	0.0142 (7)	0.0139 (8)	0.0170 (8)	0.0069 (6)	0.0049 (6)	0.0033 (6)
C6	0.0106 (7)	0.0152 (8)	0.0166 (8)	0.0062 (6)	0.0037 (6)	0.0043 (6)
O7	0.0197 (6)	0.0210 (6)	0.0163 (6)	0.0108 (5)	−0.0009 (5)	0.0011 (5)
C7	0.0115 (7)	0.0153 (8)	0.0149 (7)	0.0030 (6)	0.0035 (6)	0.0036 (6)
C8	0.0159 (8)	0.0166 (8)	0.0172 (8)	0.0066 (6)	0.0035 (6)	0.0037 (6)
C9	0.0175 (8)	0.0176 (8)	0.0156 (8)	0.0064 (7)	0.0026 (6)	−0.0006 (6)
C10	0.0189 (8)	0.0175 (8)	0.0219 (8)	0.0066 (7)	0.0051 (7)	0.0029 (7)
C11	0.0242 (9)	0.0236 (9)	0.0270 (9)	0.0045 (7)	0.0013 (7)	−0.0024 (7)

N1—C6	1.3999 (18)	C7—C8	1.499 (2)
N1—C2	1.4093 (19)	C8—C9	1.526 (2)
N1—C7	1.4526 (18)	C8—H8A	0.9900
O2—C2	1.2084 (17)	C8—H8B	0.9900
C2—N3	1.3837 (18)	C9—C10	1.520 (2)
N3—C4	1.3743 (19)	C9—H9A	0.9900
N3—H3	0.8800	C9—H9B	0.9900
O4—C4	1.2291 (17)	C10—C11	1.523 (2)
C4—C5	1.446 (2)	C10—H10A	0.9900
F5—C5	1.3462 (16)	C10—H10B	0.9900
C5—C6	1.325 (2)	C11—H11A	0.9800
C6—H6	0.9500	C11—H11B	0.9800
O7—C7	1.2077 (17)	C11—H11C	0.9800
C6—N1—C2	120.42 (12)	C9—C8—H8A	109.1
C6—N1—C7	115.53 (12)	C7—C8—H8B	109.1
C2—N1—C7	123.89 (12)	C9—C8—H8B	109.1
O2—C2—N3	121.00 (13)	H8A—C8—H8B	107.9
O2—C2—N1	124.45 (13)	C10—C9—C8	114.16 (12)
N3—C2—N1	114.55 (13)	C10—C9—H9A	108.7
C4—N3—C2	128.41 (13)	C8—C9—H9A	108.7
C4—N3—H3	115.8	C10—C9—H9B	108.7
C2—N3—H3	115.8	C8—C9—H9B	108.7
O4—C4—N3	122.41 (13)	H9A—C9—H9B	107.6
O4—C4—C5	124.89 (14)	C9—C10—C11	111.57 (13)
N3—C4—C5	112.70 (13)	C9—C10—H10A	109.3
C6—C5—F5	120.95 (13)	C11—C10—H10A	109.3
C6—C5—C4	122.57 (14)	C9—C10—H10B	109.3
F5—C5—C4	116.48 (13)	C11—C10—H10B	109.3
C5—C6—N1	121.32 (13)	H10A—C10—H10B	108.0
C5—C6—H6	119.3	C10—C11—H11A	109.5
N1—C6—H6	119.3	C10—C11—H11B	109.5
O7—C7—N1	116.83 (13)	H11A—C11—H11B	109.5
O7—C7—C8	123.69 (13)	C10—C11—H11C	109.5
N1—C7—C8	119.47 (12)	H11A—C11—H11C	109.5
C7—C8—C9	112.37 (12)	H11B—C11—H11C	109.5
C7—C8—H8A	109.1
C6—N1—C2—O2	−179.04 (14)	F5—C5—C6—N1	−179.41 (12)
C7—N1—C2—O2	−3.7 (2)	C4—C5—C6—N1	0.2 (2)
C6—N1—C2—N3	0.63 (19)	C2—N1—C6—C5	0.1 (2)
C7—N1—C2—N3	175.95 (12)	C7—N1—C6—C5	−175.62 (13)
O2—C2—N3—C4	177.79 (14)	C6—N1—C7—O7	5.59 (19)
N1—C2—N3—C4	−1.9 (2)	C2—N1—C7—O7	−169.94 (13)
C2—N3—C4—O4	−178.30 (14)	C6—N1—C7—C8	−175.64 (12)
C2—N3—C4—C5	2.1 (2)	C2—N1—C7—C8	8.8 (2)
O4—C4—C5—C6	179.25 (14)	O7—C7—C8—C9	−6.9 (2)
N3—C4—C5—C6	−1.2 (2)	N1—C7—C8—C9	174.46 (12)
O4—C4—C5—F5	−1.1 (2)	C7—C8—C9—C10	−74.69 (17)
N3—C4—C5—F5	178.46 (12)	C8—C9—C10—C11	176.35 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O4i	0.88	1.99	2.8588 (16)	170
C6—H6···O7	0.95	2.28	2.6102 (17)	100
C6—H6···O7ii	0.95	2.34	3.2266 (19)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O4i	0.88	1.99	2.8588 (16)	170
C6—H6⋯O7	0.95	2.28	2.6102 (17)	100
C6—H6⋯O7ii	0.95	2.34	3.2266 (19)	154

Symmetry codes: (i) ; (ii) .