4-(3-Fluoro-4-nitro-phen-yl)morpholin-3-one.

In the title compound, C(10)H(9)FN(2)O(4), the dihedral angle between the benzene ring and the nitro group plane is 11.29 (3)°. The morpholinone ring adopts a twist-chair conformation. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds into a chain along the a-axis direction.

Related literature

The title compound is an inter­mediate in the preparation of derivatives of the factor Xa inhibitor rivaroxaban (systematic name (S)-5-chloro-N-{[2-oxo-3-[4-(3-oxomorpholin-4-yl)phen­yl]oxazolidin-5-yl]meth­yl}thio­phene-2-carboxamide). For the bioactivity and applications of rivaroxaban, see: Pinto et al. (2010 ▶); Haas (2008 ▶); Squizzato et al. (2009 ▶); Samama & Gerotziafas (2010 ▶); Van Huis et al. (2009 ▶). For the synthesis of other derivatives with morpholone, see: Van Huis et al. (2009 ▶); Zbinden et al. (2009 ▶).

Experimental

Crystal data

C10H9FN2O4

M = 240.19

Triclinic,

a = 6.6408 (7) Å

b = 7.3788 (10) Å

c = 10.8546 (14) Å

α = 73.30 (3)°

β = 75.39 (3)°

γ = 74.30 (3)°

V = 481.60 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.14 mm−1

T = 113 K

0.22 × 0.20 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: ψ scan (CrystalClear; Rigaku/MSC, 2009 ▶) T min = 0.970, T max = 0.986

6470 measured reflections

2569 independent reflections

1734 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.104

S = 0.97

2569 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.25 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019738/kp2328sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019738/kp2328Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019738/kp2328Isup3.cml

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

C10H9FN2O4	Z = 2
Mr = 240.19	F(000) = 248
Triclinic, P1	Dx = 1.656 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6408 (7) Å	Cell parameters from 1909 reflections
b = 7.3788 (10) Å	θ = 2.0–31.1°
c = 10.8546 (14) Å	µ = 0.14 mm−1
α = 73.30 (3)°	T = 113 K
β = 75.39 (3)°	Prism, colourless
γ = 74.30 (3)°	0.22 × 0.20 × 0.10 mm
V = 481.60 (14) Å3

Rigaku Saturn CCD area-detector diffractometer	2569 independent reflections
Radiation source: rotating anode	1734 reflections with I > 2σ(I)
multilayer	Rint = 0.041
Detector resolution: 14.63 pixels mm-1	θmax = 29.1°, θmin = 2.0°
ω and φ scans	h = −9→9
Absorption correction: ψ scan (CrystalClear; Rigaku/MSC, 2009)	k = −10→9
Tmin = 0.970, Tmax = 0.986	l = −14→14
6470 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0502P)2] where P = (Fo2 + 2Fc2)/3
2569 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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
F1	0.38071 (13)	0.73231 (13)	−0.24062 (8)	0.0292 (2)
O1	0.23003 (15)	0.94560 (12)	0.40672 (8)	0.0192 (2)
O2	0.04787 (15)	0.82852 (15)	0.16307 (9)	0.0262 (2)
O3	0.74637 (16)	0.59970 (13)	−0.37865 (9)	0.0241 (2)
O4	1.03428 (15)	0.62270 (13)	−0.32888 (9)	0.0234 (2)
N1	0.39251 (16)	0.79057 (14)	0.18692 (10)	0.0139 (2)
N2	0.84043 (18)	0.63168 (15)	−0.30564 (10)	0.0165 (2)
C1	0.5325 (2)	0.77071 (18)	0.27977 (12)	0.0161 (3)
H1A	0.6152	0.8739	0.2456	0.019*
H1B	0.6347	0.6443	0.2855	0.019*
C2	0.4068 (2)	0.78419 (19)	0.41571 (12)	0.0201 (3)
H2A	0.3550	0.6634	0.4599	0.024*
H2B	0.5001	0.7996	0.4685	0.024*
C3	0.0821 (2)	0.90024 (19)	0.35316 (12)	0.0183 (3)
H3A	−0.0349	1.0155	0.3382	0.022*
H3B	0.0196	0.7956	0.4183	0.022*
C4	0.1736 (2)	0.83638 (18)	0.22515 (12)	0.0164 (3)
C5	0.4968 (2)	0.75696 (16)	0.06139 (12)	0.0132 (3)
C6	0.7205 (2)	0.71941 (17)	0.03016 (12)	0.0160 (3)
H6	0.7988	0.7192	0.0924	0.019*
C7	0.8283 (2)	0.68282 (17)	−0.09000 (12)	0.0161 (3)
H7	0.9795	0.6591	−0.1095	0.019*
C8	0.7182 (2)	0.68025 (17)	−0.18264 (12)	0.0143 (3)
C9	0.4967 (2)	0.72366 (18)	−0.15317 (12)	0.0158 (3)
C10	0.3858 (2)	0.76283 (17)	−0.03458 (12)	0.0160 (3)
H10	0.2345	0.7938	−0.0178	0.019*

	U11	U22	U33	U12	U13	U23
F1	0.0201 (5)	0.0495 (5)	0.0226 (4)	−0.0038 (4)	−0.0079 (4)	−0.0158 (4)
O1	0.0176 (5)	0.0226 (5)	0.0198 (5)	−0.0014 (4)	−0.0046 (4)	−0.0102 (4)
O2	0.0134 (5)	0.0476 (6)	0.0235 (5)	−0.0093 (5)	−0.0009 (4)	−0.0173 (5)
O3	0.0289 (6)	0.0285 (5)	0.0192 (5)	−0.0068 (4)	−0.0067 (4)	−0.0099 (4)
O4	0.0162 (5)	0.0297 (5)	0.0214 (5)	−0.0027 (4)	0.0012 (4)	−0.0078 (4)
N1	0.0125 (5)	0.0173 (5)	0.0125 (5)	−0.0031 (4)	−0.0020 (4)	−0.0049 (4)
N2	0.0192 (6)	0.0143 (5)	0.0148 (5)	−0.0029 (5)	−0.0020 (5)	−0.0028 (4)
C1	0.0135 (6)	0.0200 (7)	0.0159 (6)	−0.0013 (5)	−0.0055 (5)	−0.0056 (5)
C2	0.0196 (7)	0.0234 (7)	0.0158 (6)	0.0000 (6)	−0.0051 (5)	−0.0053 (5)
C3	0.0162 (7)	0.0218 (7)	0.0173 (6)	−0.0031 (5)	−0.0026 (5)	−0.0063 (5)
C4	0.0147 (7)	0.0177 (7)	0.0163 (6)	−0.0045 (5)	−0.0007 (5)	−0.0044 (5)
C5	0.0153 (6)	0.0117 (6)	0.0129 (6)	−0.0041 (5)	−0.0021 (5)	−0.0029 (5)
C6	0.0154 (7)	0.0182 (7)	0.0162 (6)	−0.0045 (5)	−0.0048 (5)	−0.0043 (5)
C7	0.0133 (6)	0.0181 (7)	0.0175 (6)	−0.0041 (5)	−0.0027 (5)	−0.0047 (5)
C8	0.0161 (7)	0.0134 (6)	0.0132 (6)	−0.0033 (5)	−0.0014 (5)	−0.0036 (5)
C9	0.0166 (7)	0.0180 (7)	0.0153 (6)	−0.0042 (5)	−0.0071 (5)	−0.0036 (5)
C10	0.0111 (6)	0.0188 (7)	0.0183 (6)	−0.0018 (5)	−0.0035 (5)	−0.0051 (5)

F1—C9	1.3438 (13)	C2—H2B	0.9900
O1—C3	1.4118 (14)	C3—C4	1.5223 (18)
O1—C2	1.4286 (16)	C3—H3A	0.9900
O2—C4	1.2193 (14)	C3—H3B	0.9900
O3—N2	1.2292 (13)	C5—C10	1.4050 (16)
O4—N2	1.2349 (13)	C5—C6	1.4061 (18)
N1—C4	1.3823 (16)	C6—C7	1.3831 (17)
N1—C5	1.4223 (16)	C6—H6	0.9500
N1—C1	1.4885 (15)	C7—C8	1.3910 (16)
N2—C8	1.4630 (16)	C7—H7	0.9500
C1—C2	1.5171 (18)	C8—C9	1.3912 (18)
C1—H1A	0.9900	C9—C10	1.3795 (18)
C1—H1B	0.9900	C10—H10	0.9500
C2—H2A	0.9900
C3—O1—C2	107.55 (9)	C4—C3—H3B	108.5
C4—N1—C5	123.48 (11)	H3A—C3—H3B	107.5
C4—N1—C1	120.11 (10)	O2—C4—N1	124.24 (12)
C5—N1—C1	116.39 (10)	O2—C4—C3	117.50 (12)
O3—N2—O4	123.82 (11)	N1—C4—C3	118.25 (11)
O3—N2—C8	118.74 (11)	C10—C5—C6	118.08 (11)
O4—N2—C8	117.43 (10)	C10—C5—N1	122.88 (11)
N1—C1—C2	112.26 (10)	C6—C5—N1	119.03 (11)
N1—C1—H1A	109.2	C7—C6—C5	120.88 (12)
C2—C1—H1A	109.2	C7—C6—H6	119.6
N1—C1—H1B	109.2	C5—C6—H6	119.6
C2—C1—H1B	109.2	C6—C7—C8	120.88 (12)
H1A—C1—H1B	107.9	C6—C7—H7	119.6
O1—C2—C1	109.95 (10)	C8—C7—H7	119.6
O1—C2—H2A	109.7	C7—C8—C9	118.10 (12)
C1—C2—H2A	109.7	C7—C8—N2	118.60 (11)
O1—C2—H2B	109.7	C9—C8—N2	123.31 (11)
C1—C2—H2B	109.7	F1—C9—C10	116.88 (12)
H2A—C2—H2B	108.2	F1—C9—C8	121.12 (12)
O1—C3—C4	114.95 (11)	C10—C9—C8	121.99 (12)
O1—C3—H3A	108.5	C9—C10—C5	119.97 (12)
C4—C3—H3A	108.5	C9—C10—H10	120.0
O1—C3—H3B	108.5	C5—C10—H10	120.0
C4—N1—C1—C2	6.24 (15)	N1—C5—C6—C7	178.93 (10)
C5—N1—C1—C2	−172.77 (10)	C5—C6—C7—C8	−0.66 (19)
C3—O1—C2—C1	70.39 (13)	C6—C7—C8—C9	2.70 (19)
N1—C1—C2—O1	−46.84 (14)	C6—C7—C8—N2	−177.12 (11)
C2—O1—C3—C4	−52.83 (13)	O3—N2—C8—C7	168.82 (11)
C5—N1—C4—O2	9.8 (2)	O4—N2—C8—C7	−10.19 (16)
C1—N1—C4—O2	−169.11 (11)	O3—N2—C8—C9	−10.99 (18)
C5—N1—C4—C3	−170.40 (11)	O4—N2—C8—C9	170.00 (11)
C1—N1—C4—C3	10.66 (17)	C7—C8—C9—F1	176.97 (10)
O1—C3—C4—O2	−167.37 (11)	N2—C8—C9—F1	−3.22 (19)
O1—C3—C4—N1	12.84 (16)	C7—C8—C9—C10	−1.95 (19)
C4—N1—C5—C10	−1.57 (18)	N2—C8—C9—C10	177.87 (11)
C1—N1—C5—C10	177.41 (11)	F1—C9—C10—C5	−179.83 (10)
C4—N1—C5—C6	177.30 (11)	C8—C9—C10—C5	−0.87 (19)
C1—N1—C5—C6	−3.73 (16)	C6—C5—C10—C9	2.90 (18)
C10—C5—C6—C7	−2.16 (18)	N1—C5—C10—C9	−178.23 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.95	2.39	3.2635 (16)	153
C2—H2B···O3ii	0.99	2.50	3.3244 (19)	140
C1—H1B···O4iii	0.99	2.57	3.515 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.95	2.39	3.2635 (16)	153
C2—H2B⋯O3ii	0.99	2.50	3.3244 (19)	140
C1—H1B⋯O4iii	0.99	2.57	3.515 (2)	161

Symmetry codes: (i) ; (ii) ; (iii) .