5-Fluoro-1-(3-metylbutano-yl)pyrimidine-2,4(1H,3H)-dione.

The 3-methyl-butanoyl group and the 5-fluoro-uracil unit of the title compound, C(9)H(11)FN(2)O(3), are essentially coplanar, with the carbonyl group oriented towards the ring CH group and away from the nearer ring carbonyl group. The 3-methyl-butanoyl (C=)C-N-C=O torsion angle of 9.6 (2)° is comparable to that in structurally related compounds. In the solid state, two inversion-related mol-ecules form N-H⋯O hydrogen bonds to generate an inter-molecular R(2) (2)(8) ring. The crystal structure also diplays 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. (1993 ▶); Jiang et al. (1988 ▶); Lehmler & Parkin (2000 ▶); Lehmler & Parkin (2008 ▶). For related literature, see: Roberts & Sloan (1999 ▶).

Experimental

Crystal data

C9H11FN2O3

M = 214.20

Triclinic,

a = 5.4879 (3) Å

b = 9.3702 (5) Å

c = 9.9794 (5) Å

α = 103.470 (2)°

β = 100.204 (3)°

γ = 104.085 (3)°

V = 468.94 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 90.0 (2) K

0.30 × 0.20 × 0.07 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.963, T max = 0.991

4080 measured reflections

2139 independent reflections

1629 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.112

S = 1.07

2139 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.29 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/S1600536808006296/om2217sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006296/om2217Isup2.hkl

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

C9H11FN2O3	Z = 2
Mr = 214.20	F000 = 224
Triclinic, P1	Dx = 1.517 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.4879 (3) Å	Cell parameters from 4363 reflections
b = 9.3702 (5) Å	θ = 1.0–27.5º
c = 9.9794 (5) Å	µ = 0.13 mm−1
α = 103.470 (2)º	T = 90.0 (2) K
β = 100.204 (3)º	Irregular block, colourless
γ = 104.085 (3)º	0.30 × 0.20 × 0.07 mm
V = 468.94 (4) Å3

Nonius KappaCCD diffractometer	2139 independent reflections
Radiation source: fine-focus sealed tube	1629 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
Detector resolution: 18 pixels mm-1	θmax = 27.5º
T = 88.0(2) K	θmin = 2.2º
ω scans at fixed χ = 55°	h = −7→7
Absorption correction: multi-scan(SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
Tmin = 0.963, Tmax = 0.991	l = −12→12
4080 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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0498P)2 + 0.0466P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2139 reflections	Δρmax = 0.27 e Å−3
138 parameters	Δρmin = −0.29 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	0.0774 (2)	0.62396 (13)	0.89316 (12)	0.0141 (3)
O2	−0.2469 (2)	0.74248 (12)	0.89048 (11)	0.0206 (3)
C2	−0.1490 (3)	0.65330 (17)	0.82969 (16)	0.0152 (3)
N3	−0.2565 (2)	0.56922 (13)	0.68799 (12)	0.0153 (3)
H3	−0.3906	0.5911	0.6444	0.018*
O4	−0.2928 (2)	0.38819 (11)	0.48195 (10)	0.0189 (3)
C4	−0.1798 (3)	0.45604 (16)	0.60712 (15)	0.0157 (4)
F5	0.13171 (17)	0.31908 (10)	0.61287 (9)	0.0218 (3)
C5	0.0440 (3)	0.42855 (17)	0.68495 (16)	0.0155 (3)
C6	0.1651 (3)	0.50812 (16)	0.81867 (15)	0.0152 (3)
H6	0.3130	0.4864	0.8646	0.018*
O7	0.3841 (2)	0.64683 (11)	1.08882 (11)	0.0195 (3)
C7	0.2244 (3)	0.70161 (17)	1.03933 (15)	0.0157 (4)
C8	0.1692 (3)	0.84157 (17)	1.12009 (15)	0.0168 (4)
H8A	0.0015	0.8099	1.1450	0.020*
H8B	0.1534	0.9094	1.0584	0.020*
C9	0.3816 (3)	0.93148 (18)	1.25622 (16)	0.0210 (4)
H9	0.4364	0.8564	1.3022	0.025*
C10	0.6162 (3)	1.02656 (19)	1.22141 (19)	0.0308 (4)
H10A	0.5657	1.1010	1.1765	0.046*
H10B	0.6817	0.9586	1.1561	0.046*
H10C	0.7522	1.0813	1.3092	0.046*
C11	0.2765 (3)	1.03360 (19)	1.35944 (16)	0.0255 (4)
H11A	0.4155	1.0936	1.4447	0.038*
H11B	0.1349	0.9693	1.3864	0.038*
H11C	0.2115	1.1034	1.3136	0.038*

	U11	U22	U33	U12	U13	U23
N1	0.0142 (7)	0.0140 (6)	0.0140 (7)	0.0062 (5)	0.0024 (5)	0.0027 (5)
O2	0.0191 (6)	0.0240 (6)	0.0184 (6)	0.0123 (5)	0.0021 (5)	0.0017 (5)
C2	0.0138 (8)	0.0165 (8)	0.0143 (8)	0.0023 (6)	0.0027 (6)	0.0055 (6)
N3	0.0128 (7)	0.0175 (7)	0.0154 (7)	0.0073 (6)	−0.0001 (5)	0.0043 (5)
O4	0.0185 (6)	0.0183 (6)	0.0160 (6)	0.0043 (5)	0.0004 (5)	0.0019 (5)
C4	0.0162 (9)	0.0131 (8)	0.0162 (8)	0.0023 (6)	0.0028 (6)	0.0045 (6)
F5	0.0236 (6)	0.0210 (5)	0.0199 (5)	0.0121 (4)	0.0036 (4)	−0.0002 (4)
C5	0.0170 (8)	0.0136 (7)	0.0181 (8)	0.0076 (6)	0.0066 (6)	0.0036 (6)
C6	0.0148 (8)	0.0154 (8)	0.0174 (8)	0.0069 (6)	0.0036 (6)	0.0062 (6)
O7	0.0201 (6)	0.0225 (6)	0.0169 (6)	0.0108 (5)	0.0010 (5)	0.0059 (5)
C7	0.0148 (9)	0.0172 (8)	0.0146 (8)	0.0027 (7)	0.0030 (6)	0.0064 (6)
C8	0.0180 (9)	0.0174 (8)	0.0159 (8)	0.0075 (7)	0.0027 (6)	0.0049 (6)
C9	0.0219 (9)	0.0193 (8)	0.0197 (9)	0.0101 (7)	−0.0027 (7)	0.0032 (7)
C10	0.0203 (10)	0.0263 (10)	0.0366 (11)	0.0061 (8)	0.0008 (8)	−0.0029 (8)
C11	0.0306 (10)	0.0217 (9)	0.0194 (9)	0.0073 (8)	0.0002 (7)	0.0018 (7)

N1—C6	1.4026 (18)	C7—C8	1.499 (2)
N1—C2	1.4102 (19)	C8—C9	1.530 (2)
N1—C7	1.4529 (18)	C8—H8A	0.9900
O2—C2	1.2053 (17)	C8—H8B	0.9900
C2—N3	1.3884 (18)	C9—C10	1.522 (2)
N3—C4	1.3755 (19)	C9—C11	1.526 (2)
N3—H3	0.8800	C9—H9	1.0000
O4—C4	1.2300 (17)	C10—H10A	0.9800
C4—C5	1.445 (2)	C10—H10B	0.9800
F5—C5	1.3493 (16)	C10—H10C	0.9800
C5—C6	1.326 (2)	C11—H11A	0.9800
C6—H6	0.9500	C11—H11B	0.9800
O7—C7	1.2079 (17)	C11—H11C	0.9800
C6—N1—C2	120.64 (12)	C9—C8—H8A	109.1
C6—N1—C7	115.63 (12)	C7—C8—H8B	109.1
C2—N1—C7	123.62 (12)	C9—C8—H8B	109.1
O2—C2—N3	121.20 (14)	H8A—C8—H8B	107.9
O2—C2—N1	124.36 (13)	C10—C9—C11	110.92 (13)
N3—C2—N1	114.44 (13)	C10—C9—C8	110.36 (13)
C4—N3—C2	128.19 (13)	C11—C9—C8	110.06 (13)
C4—N3—H3	115.9	C10—C9—H9	108.5
C2—N3—H3	115.9	C11—C9—H9	108.5
O4—C4—N3	122.26 (14)	C8—C9—H9	108.5
O4—C4—C5	125.01 (14)	C9—C10—H10A	109.5
N3—C4—C5	112.73 (13)	C9—C10—H10B	109.5
C6—C5—F5	120.63 (13)	H10A—C10—H10B	109.5
C6—C5—C4	122.96 (14)	C9—C10—H10C	109.5
F5—C5—C4	116.38 (12)	H10A—C10—H10C	109.5
C5—C6—N1	120.82 (14)	H10B—C10—H10C	109.5
C5—C6—H6	119.6	C9—C11—H11A	109.5
N1—C6—H6	119.6	C9—C11—H11B	109.5
O7—C7—N1	116.87 (13)	H11A—C11—H11B	109.5
O7—C7—C8	123.93 (13)	C9—C11—H11C	109.5
N1—C7—C8	119.20 (12)	H11A—C11—H11C	109.5
C7—C8—C9	112.30 (13)	H11B—C11—H11C	109.5
C7—C8—H8A	109.1
C6—N1—C2—O2	174.10 (14)	F5—C5—C6—N1	178.82 (12)
C7—N1—C2—O2	−1.8 (2)	C4—C5—C6—N1	0.9 (2)
C6—N1—C2—N3	−5.5 (2)	C2—N1—C6—C5	3.1 (2)
C7—N1—C2—N3	178.58 (12)	C7—N1—C6—C5	179.32 (13)
O2—C2—N3—C4	−174.94 (14)	C6—N1—C7—O7	−9.6 (2)
N1—C2—N3—C4	4.7 (2)	C2—N1—C7—O7	166.53 (13)
C2—N3—C4—O4	179.30 (13)	C6—N1—C7—C8	171.17 (12)
C2—N3—C4—C5	−1.1 (2)	C2—N1—C7—C8	−12.7 (2)
O4—C4—C5—C6	177.69 (15)	O7—C7—C8—C9	15.1 (2)
N3—C4—C5—C6	−1.9 (2)	N1—C7—C8—C9	−165.67 (13)
O4—C4—C5—F5	−0.3 (2)	C7—C8—C9—C10	78.01 (16)
N3—C4—C5—F5	−179.92 (12)	C7—C8—C9—C11	−159.23 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O4i	0.88	2.04	2.9091 (16)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O4i	0.88	2.04	2.9091 (16)	171

Symmetry code: (i) .