Ethyl 4-fluoro-3-nitro-benzoate.

In the title compound, C(9)H(8)FNO(4), C-H⋯O inter-molecular inter-actions form dimers with R(2) (2)(10) motifs. These dimers are arranged into chains parallel to the b axis and the chains are stacked down the c axis.

Related literature

For general background, see: Ishida et al. (2006 ▶); Rida et al. (2005 ▶); Mohd. Maidin, Abdul Rahim, Abdul Hamid et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Mohd. Maidin, Abdul Rahim, Osman et al. (2008 ▶); Li et al. (2008 ▶, 2009 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For details on the stability of the temperature controller, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C9H8FNO4

M = 213.16

Monoclinic,

a = 9.9246 (3) Å

b = 13.2883 (3) Å

c = 6.9310 (2) Å

β = 94.410 (2)°

V = 911.36 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 100 K

0.55 × 0.22 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.929, T max = 0.988

12540 measured reflections

2913 independent reflections

2411 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.139

S = 1.11

2913 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005224/at2723sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005224/at2723Isup2.hkl

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

C9H8FNO4	F(000) = 440
Mr = 213.16	Dx = 1.554 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5027 reflections
a = 9.9246 (3) Å	θ = 2.6–30.8°
b = 13.2883 (3) Å	µ = 0.14 mm−1
c = 6.9310 (2) Å	T = 100 K
β = 94.410 (2)°	Block, colourless
V = 911.36 (4) Å3	0.55 × 0.22 × 0.09 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2913 independent reflections
Radiation source: sealed tube	2411 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 31.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
Tmin = 0.929, Tmax = 0.988	k = −18→19
12540 measured reflections	l = −10→10

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-atom parameters constrained
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.0772P)2 + 0.1955P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
2913 reflections	Δρmax = 0.55 e Å−3
138 parameters	Δρmin = −0.36 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (4)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.04351 (7)	0.10679 (6)	0.18019 (12)	0.0241 (2)
O1	0.07165 (9)	0.29746 (7)	0.29028 (14)	0.0240 (2)
O2	−0.04092 (9)	0.39394 (6)	0.08249 (15)	0.0247 (2)
O3	−0.52330 (8)	0.30897 (6)	−0.00372 (14)	0.0203 (2)
O4	−0.58597 (9)	0.14638 (7)	−0.02358 (16)	0.0276 (2)
N1	−0.02296 (10)	0.31401 (7)	0.16902 (15)	0.0172 (2)
C1	−0.31523 (12)	0.08546 (9)	0.06256 (18)	0.0197 (2)
H1A	−0.3804	0.0356	0.0410	0.024*
C2	−0.18146 (12)	0.05833 (9)	0.10726 (19)	0.0211 (3)
H2A	−0.1566	−0.0091	0.1139	0.025*
C3	−0.08581 (11)	0.13301 (9)	0.14173 (17)	0.0181 (2)
C4	−0.12280 (11)	0.23409 (8)	0.12960 (16)	0.0154 (2)
C5	−0.25648 (11)	0.26145 (8)	0.08154 (16)	0.0154 (2)
H5A	−0.2807	0.3290	0.0710	0.018*
C6	−0.35338 (11)	0.18648 (8)	0.04945 (17)	0.0161 (2)
C7	−0.49936 (11)	0.21032 (9)	0.00323 (18)	0.0179 (2)
C8	−0.66549 (12)	0.33789 (10)	−0.0398 (2)	0.0231 (3)
H8A	−0.7170	0.3145	0.0648	0.028*
H8B	−0.7035	0.3081	−0.1597	0.028*
C9	−0.67127 (13)	0.45039 (10)	−0.0529 (2)	0.0280 (3)
H9A	−0.7638	0.4716	−0.0713	0.042*
H9B	−0.6233	0.4725	−0.1603	0.042*
H9C	−0.6304	0.4791	0.0646	0.042*

	U11	U22	U33	U12	U13	U23
F1	0.0168 (3)	0.0239 (4)	0.0312 (4)	0.0077 (3)	0.0003 (3)	0.0020 (3)
O1	0.0153 (4)	0.0295 (5)	0.0264 (5)	0.0006 (3)	−0.0037 (3)	0.0008 (4)
O2	0.0228 (4)	0.0174 (4)	0.0333 (5)	−0.0018 (3)	−0.0025 (4)	0.0042 (4)
O3	0.0123 (4)	0.0155 (4)	0.0324 (5)	0.0009 (3)	−0.0017 (3)	0.0002 (3)
O4	0.0191 (4)	0.0176 (4)	0.0453 (6)	−0.0038 (3)	−0.0041 (4)	0.0012 (4)
N1	0.0141 (4)	0.0180 (5)	0.0196 (5)	0.0007 (3)	0.0017 (3)	−0.0015 (4)
C1	0.0201 (5)	0.0148 (5)	0.0242 (6)	−0.0008 (4)	0.0010 (4)	−0.0002 (4)
C2	0.0229 (6)	0.0140 (5)	0.0263 (6)	0.0037 (4)	0.0015 (5)	0.0004 (4)
C3	0.0166 (5)	0.0185 (5)	0.0192 (5)	0.0049 (4)	0.0015 (4)	0.0006 (4)
C4	0.0144 (5)	0.0158 (5)	0.0159 (5)	0.0007 (4)	0.0010 (4)	0.0001 (4)
C5	0.0144 (5)	0.0149 (5)	0.0169 (5)	0.0018 (4)	0.0014 (4)	0.0005 (4)
C6	0.0148 (5)	0.0152 (5)	0.0181 (5)	0.0005 (4)	0.0004 (4)	−0.0001 (4)
C7	0.0157 (5)	0.0162 (5)	0.0216 (5)	−0.0003 (4)	0.0005 (4)	0.0003 (4)
C8	0.0119 (5)	0.0218 (6)	0.0350 (7)	0.0007 (4)	−0.0013 (4)	0.0022 (5)
C9	0.0188 (6)	0.0213 (6)	0.0426 (8)	0.0040 (4)	−0.0050 (5)	−0.0051 (5)

F1—C3	1.3368 (13)	C3—C4	1.3932 (16)
O1—N1	1.2308 (13)	C4—C5	1.3912 (14)
O2—N1	1.2261 (13)	C5—C6	1.3906 (15)
O3—C7	1.3326 (14)	C5—H5A	0.9300
O3—C8	1.4653 (13)	C6—C7	1.4935 (15)
O4—C7	1.2127 (14)	C8—C9	1.4984 (19)
N1—C4	1.4638 (15)	C8—H8A	0.9700
C1—C2	1.3876 (16)	C8—H8B	0.9700
C1—C6	1.3959 (16)	C9—H9A	0.9600
C1—H1A	0.9300	C9—H9B	0.9600
C2—C3	1.3814 (17)	C9—H9C	0.9600
C2—H2A	0.9300
C7—O3—C8	115.52 (9)	C5—C6—C1	119.85 (10)
O2—N1—O1	124.29 (10)	C5—C6—C7	122.00 (10)
O2—N1—C4	117.80 (9)	C1—C6—C7	118.14 (10)
O1—N1—C4	117.89 (10)	O4—C7—O3	124.15 (11)
C2—C1—C6	120.96 (11)	O4—C7—C6	123.28 (11)
C2—C1—H1A	119.5	O3—C7—C6	112.57 (9)
C6—C1—H1A	119.5	O3—C8—C9	107.69 (9)
C3—C2—C1	119.01 (11)	O3—C8—H8A	110.2
C3—C2—H2A	120.5	C9—C8—H8A	110.2
C1—C2—H2A	120.5	O3—C8—H8B	110.2
F1—C3—C2	118.93 (10)	C9—C8—H8B	110.2
F1—C3—C4	120.52 (10)	H8A—C8—H8B	108.5
C2—C3—C4	120.51 (10)	C8—C9—H9A	109.5
C5—C4—C3	120.56 (10)	C8—C9—H9B	109.5
C5—C4—N1	118.32 (10)	H9A—C9—H9B	109.5
C3—C4—N1	121.11 (10)	C8—C9—H9C	109.5
C6—C5—C4	119.08 (10)	H9A—C9—H9C	109.5
C6—C5—H5A	120.5	H9B—C9—H9C	109.5
C4—C5—H5A	120.5
C6—C1—C2—C3	0.93 (19)	N1—C4—C5—C6	−178.04 (10)
C1—C2—C3—F1	−178.41 (11)	C4—C5—C6—C1	−1.07 (18)
C1—C2—C3—C4	−0.74 (19)	C4—C5—C6—C7	178.12 (10)
F1—C3—C4—C5	177.27 (10)	C2—C1—C6—C5	−0.02 (19)
C2—C3—C4—C5	−0.36 (18)	C2—C1—C6—C7	−179.25 (11)
F1—C3—C4—N1	−3.44 (17)	C8—O3—C7—O4	2.20 (18)
C2—C3—C4—N1	178.93 (11)	C8—O3—C7—C6	−177.35 (10)
O2—N1—C4—C5	−31.36 (16)	C5—C6—C7—O4	−179.29 (12)
O1—N1—C4—C5	146.88 (11)	C1—C6—C7—O4	−0.09 (19)
O2—N1—C4—C3	149.33 (12)	C5—C6—C7—O3	0.26 (16)
O1—N1—C4—C3	−32.42 (16)	C1—C6—C7—O3	179.47 (11)
C3—C4—C5—C6	1.27 (17)	C7—O3—C8—C9	−177.07 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O4i	0.93	2.44	3.2380 (15)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O4i	0.93	2.44	3.2380 (15)	144

Symmetry code: (i) .