5-(4-Fluoro-phen-yl)-5-methyl-imidazolidine-2,4-dione.

In the title compound, C(10)H(9)FN(2)O(2), the dihedral angle between the hydantoin unit and the benzene ring is 65.55 (5)°. The atoms in the hydantoin ring are coplanar, with a mean deviation of 0.015 Å and a maximum deviation of 0.075 (2) Å for one carbonyl O atom. N-H⋯O hydrogen bonds link the mol-ecules into one-dimensional chains, with one carbonyl group acting as a bifurcated acceptor and the other accepting no hydrogen bonds.

Related literature

For related literature, see: Ahmad et al. (2000 ▶, 2002 ▶); Balavoine et al. (2007 ▶); Mullica et al. (1998 ▶); Park et al. (2007 ▶); Rajic et al. (2006 ▶); Sheppeck et al. (2007 ▶).

Experimental

Crystal data

C10H9FN2O2

M = 208.19

Orthorhombic,

a = 7.096 (2) Å

b = 11.348 (3) Å

c = 22.661 (7) Å

V = 1824.7 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 123 (2) K

0.34 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: none

13516 measured reflections

2083 independent reflections

2054 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.094

S = 1.22

2083 reflections

145 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: TEXSAN (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and TEXSAN.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067803/bi2269sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067803/bi2269Isup2.hkl

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

C10H9FN2O2	F000 = 864
Mr = 208.19	Dx = 1.516 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71070 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5426 reflections
a = 7.096 (2) Å	θ = 3.0–27.5º
b = 11.348 (3) Å	µ = 0.12 mm−1
c = 22.661 (7) Å	T = 123 (2) K
V = 1824.7 (10) Å3	Block, colorless
Z = 8	0.34 × 0.30 × 0.20 mm

Rigaku Mercury CCD diffractometer	2054 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
Detector resolution: 14.62 pixels mm-1	θmax = 27.5º
T = 123(2) K	θmin = 3.5º
ω scans	h = −9→8
Absorption correction: none	k = −14→13
13516 measured reflections	l = −17→29
2083 independent 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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.028P)2 + 1.2798P] where P = (Fo2 + 2Fc2)/3
S = 1.22	(Δ/σ)max = 0.001
2083 reflections	Δρmax = 0.31 e Å−3
145 parameters	Δρmin = −0.16 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 > 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.

	x	y	z	Uiso*/Ueq
C1	0.13701 (19)	0.06340 (11)	0.10194 (6)	0.0127 (3)
N1	0.09007 (16)	0.16162 (10)	0.06286 (5)	0.0141 (2)
H1	−0.025 (3)	0.1859 (17)	0.0547 (9)	0.028 (5)*
C2	0.23589 (19)	0.19597 (12)	0.02932 (6)	0.0135 (3)
O1	0.23772 (14)	0.27474 (9)	−0.00808 (4)	0.0167 (2)
N2	0.38961 (17)	0.12558 (10)	0.04332 (5)	0.0151 (3)
H2	0.504 (3)	0.1445 (16)	0.0305 (8)	0.024 (5)*
C3	0.34432 (19)	0.04077 (11)	0.08415 (6)	0.0129 (3)
O2	0.44614 (15)	−0.03631 (8)	0.10246 (4)	0.0177 (2)
C4	0.13117 (18)	0.09904 (11)	0.16706 (6)	0.0118 (3)
C5	0.08781 (19)	0.21387 (12)	0.18428 (6)	0.0150 (3)
H5	0.0607	0.2719	0.1553	0.018*
C6	0.0841 (2)	0.24367 (12)	0.24395 (6)	0.0175 (3)
H6	0.0542	0.3217	0.2560	0.021*
C7	0.1246 (2)	0.15835 (13)	0.28513 (6)	0.0170 (3)
C8	0.1685 (2)	0.04404 (12)	0.26982 (6)	0.0158 (3)
H8	0.1954	−0.0134	0.2992	0.019*
C9	0.17244 (19)	0.01526 (12)	0.21023 (6)	0.0139 (3)
H9	0.2037	−0.0628	0.1987	0.017*
C10	0.0141 (2)	−0.04446 (12)	0.08893 (6)	0.0183 (3)
H10A	−0.1179	−0.0258	0.0975	0.027*
H10B	0.0549	−0.1105	0.1137	0.027*
H10C	0.0267	−0.0660	0.0472	0.027*
F1	0.12297 (14)	0.18871 (8)	0.34320 (4)	0.0258 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0126 (6)	0.0140 (6)	0.0116 (6)	−0.0001 (5)	−0.0008 (5)	0.0028 (5)
N1	0.0104 (5)	0.0188 (6)	0.0132 (5)	0.0008 (4)	−0.0007 (4)	0.0057 (4)
C2	0.0120 (6)	0.0168 (6)	0.0115 (6)	−0.0011 (5)	−0.0016 (5)	−0.0003 (5)
O1	0.0127 (5)	0.0210 (5)	0.0166 (5)	0.0002 (4)	0.0000 (4)	0.0079 (4)
N2	0.0112 (6)	0.0183 (6)	0.0159 (6)	0.0004 (4)	0.0011 (4)	0.0053 (5)
C3	0.0145 (6)	0.0138 (6)	0.0105 (6)	−0.0007 (5)	0.0001 (5)	−0.0003 (5)
O2	0.0183 (5)	0.0163 (5)	0.0186 (5)	0.0042 (4)	0.0014 (4)	0.0030 (4)
C4	0.0092 (6)	0.0147 (6)	0.0115 (6)	−0.0016 (5)	0.0008 (5)	0.0009 (5)
C5	0.0145 (6)	0.0137 (6)	0.0169 (6)	−0.0010 (5)	0.0012 (5)	0.0026 (5)
C6	0.0172 (7)	0.0145 (6)	0.0209 (7)	−0.0014 (5)	0.0052 (5)	−0.0037 (5)
C7	0.0155 (7)	0.0229 (7)	0.0125 (6)	−0.0043 (5)	0.0030 (5)	−0.0042 (5)
C8	0.0147 (6)	0.0194 (6)	0.0132 (6)	−0.0015 (5)	0.0001 (5)	0.0037 (5)
C9	0.0136 (6)	0.0133 (6)	0.0148 (6)	0.0002 (5)	0.0007 (5)	0.0009 (5)
C10	0.0200 (7)	0.0196 (7)	0.0152 (6)	−0.0070 (5)	−0.0006 (5)	−0.0002 (5)
F1	0.0347 (5)	0.0288 (5)	0.0140 (4)	−0.0055 (4)	0.0051 (4)	−0.0061 (4)

C1—N1	1.4620 (17)	C5—C6	1.394 (2)
C1—C4	1.5306 (18)	C5—H5	0.950
C1—C10	1.5316 (19)	C6—C7	1.375 (2)
C1—C3	1.5468 (19)	C6—H6	0.950
N1—C2	1.3417 (18)	C7—F1	1.3604 (16)
N1—H1	0.88 (2)	C7—C8	1.378 (2)
C2—O1	1.2320 (17)	C8—C9	1.3897 (19)
C2—N2	1.3887 (18)	C8—H8	0.950
N2—C3	1.3732 (17)	C9—H9	0.950
N2—H2	0.89 (2)	C10—H10A	0.980
C3—O2	1.2080 (17)	C10—H10B	0.980
C4—C5	1.3946 (19)	C10—H10C	0.980
C4—C9	1.3952 (18)
N1—C1—C4	112.11 (11)	C6—C5—C4	120.14 (13)
N1—C1—C10	111.28 (11)	C6—C5—H5	119.9
C4—C1—C10	112.42 (11)	C4—C5—H5	119.9
N1—C1—C3	100.68 (10)	C7—C6—C5	118.92 (13)
C4—C1—C3	108.71 (10)	C7—C6—H6	120.5
C10—C1—C3	111.03 (11)	C5—C6—H6	120.5
C2—N1—C1	112.89 (11)	F1—C7—C6	118.45 (13)
C2—N1—H1	120.3 (13)	F1—C7—C8	118.92 (13)
C1—N1—H1	125.2 (13)	C6—C7—C8	122.62 (13)
O1—C2—N1	127.49 (13)	C7—C8—C9	118.05 (12)
O1—C2—N2	124.48 (12)	C7—C8—H8	121.0
N1—C2—N2	108.02 (11)	C9—C8—H8	121.0
C3—N2—C2	111.91 (11)	C8—C9—C4	121.13 (12)
C3—N2—H2	127.1 (12)	C8—C9—H9	119.4
C2—N2—H2	120.3 (12)	C4—C9—H9	119.4
O2—C3—N2	126.79 (13)	C1—C10—H10A	109.5
O2—C3—C1	126.84 (12)	C1—C10—H10B	109.5
N2—C3—C1	106.37 (11)	H10A—C10—H10B	109.5
C5—C4—C9	119.13 (12)	C1—C10—H10C	109.5
C5—C4—C1	121.51 (12)	H10A—C10—H10C	109.5
C9—C4—C1	119.35 (12)	H10B—C10—H10C	109.5
C4—C1—N1—C2	113.75 (13)	C10—C1—C4—C5	−127.12 (14)
C10—C1—N1—C2	−119.38 (13)	C3—C1—C4—C5	109.54 (14)
C3—C1—N1—C2	−1.65 (14)	N1—C1—C4—C9	179.95 (12)
C1—N1—C2—O1	178.84 (13)	C10—C1—C4—C9	53.70 (17)
C1—N1—C2—N2	−0.49 (15)	C3—C1—C4—C9	−69.63 (15)
O1—C2—N2—C3	−176.54 (13)	C9—C4—C5—C6	−0.6 (2)
N1—C2—N2—C3	2.81 (16)	C1—C4—C5—C6	−179.82 (12)
C2—N2—C3—O2	176.10 (13)	C4—C5—C6—C7	0.3 (2)
C2—N2—C3—C1	−3.79 (15)	C5—C6—C7—F1	179.19 (12)
N1—C1—C3—O2	−176.71 (13)	C5—C6—C7—C8	−0.1 (2)
C4—C1—C3—O2	65.37 (17)	F1—C7—C8—C9	−178.99 (12)
C10—C1—C3—O2	−58.79 (17)	C6—C7—C8—C9	0.3 (2)
N1—C1—C3—N2	3.18 (13)	C7—C8—C9—C4	−0.7 (2)
C4—C1—C3—N2	−114.74 (12)	C5—C4—C9—C8	0.9 (2)
C10—C1—C3—N2	121.09 (12)	C1—C4—C9—C8	−179.95 (12)
N1—C1—C4—C5	−0.87 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88 (2)	2.04 (2)	2.8834 (17)	160.5 (18)
N2—H2···O1ii	0.89 (2)	1.96 (2)	2.8318 (17)	165.9 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88 (2)	2.04 (2)	2.8834 (17)	160.5 (18)
N2—H2⋯O1ii	0.89 (2)	1.96 (2)	2.8318 (17)	165.9 (17)

Symmetry codes: (i) ; (ii) .