2-Fluoro-4-(meth-oxy-carbon-yl)benzoic acid.

In the crystal of the title compound, C(9)H(7)FO(4), classical carboxylate inversion dimers are linked by pairs of O-H⋯O hydrogen bonds. The packing is consolidated by C-H⋯F and C-H⋯O interactions. The benzene ring and the methoxycarbonyl group are nearly coplanar, with a dihedral angle of 1.5 (3)° between them, whereas the carboxyl group has a dihedral angle of 20.2 (4)° with respect to the benzene ring.

Related literature

For background to the applications of the title compound, see: Jiang et al. (2008 ▶); Sakaki et al. (2007 ▶). For related structures, see: Wagner et al. (2009 ▶).

Experimental

Crystal data

C9H7FO4

M = 198.15

Triclinic,

a = 7.536 (7) Å

b = 7.591 (7) Å

c = 8.523 (8) Å

α = 99.480 (14)°

β = 108.748 (13)°

γ = 99.240 (14)°

V = 443.3 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.25 × 0.19 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.969, T max = 0.990

2526 measured reflections

1535 independent reflections

1025 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.190

S = 1.02

1535 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XSHELL (Bruker, 2004 ▶); software used to prepare material for publication: APEX2.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032253/pb2036sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032253/pb2036Isup2.hkl

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

C9H7FO4	Z = 2
Mr = 198.15	F(000) = 204
Triclinic, P1	Dx = 1.484 Mg m−3
Hall symbol: -P 1	Melting point: 427 K
a = 7.536 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.591 (7) Å	Cell parameters from 51 reflections
c = 8.523 (8) Å	θ = 4.5–11.9°
α = 99.480 (14)°	µ = 0.13 mm−1
β = 108.748 (13)°	T = 296 K
γ = 99.240 (14)°	Plate, colourless
V = 443.3 (7) Å3	0.25 × 0.19 × 0.08 mm

Bruker SMART APEX CCD diffractometer	1535 independent reflections
Radiation source: sealed tube	1025 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω and φ scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→8
Tmin = 0.969, Tmax = 0.990	k = −9→8
2526 measured reflections	l = −10→10

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.P)2 + 0.1145P] where P = (Fo2 + 2Fc2)/3
1535 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 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.H atoms were placed geometrically and allowed to refine as atoms riding on their bonding partners. The hydrogen was placed on the carboxylic acid based on the longer of the carboxylic acid carbon-oxygen bonds.

	x	y	z	Uiso*/Ueq
F1	0.4739 (2)	1.3542 (2)	0.6014 (2)	0.0629 (5)
O1	0.8299 (2)	1.4232 (4)	0.5841 (2)	0.0672 (7)
O2	0.8296 (2)	1.3413 (2)	0.3192 (2)	0.0716 (8)
H2A	0.9326	1.4171	0.3603	0.107*
O3	−0.1230 (4)	0.8633 (4)	0.2593 (2)	0.0798 (9)
O4	−0.0485 (2)	0.7256 (2)	0.0437 (2)	0.0582 (7)
C1	0.5568 (4)	1.2070 (4)	0.3734 (2)	0.0453 (7)
C2	0.4248 (4)	1.2212 (4)	0.4562 (2)	0.0464 (7)
C3	0.2443 (4)	1.1083 (4)	0.3967 (2)	0.0479 (8)
H3A	0.1607	1.1227	0.4553	0.057*
C4	0.1871 (4)	0.9720 (4)	0.2478 (2)	0.0437 (7)
C5	0.3166 (4)	0.9507 (4)	0.1625 (2)	0.0495 (8)
H5A	0.2807	0.8584	0.0642	0.059*
C6	0.4976 (5)	1.0670 (4)	0.2248 (4)	0.0527 (8)
H6A	0.5819	1.0523	0.1669	0.063*
C7	0.7527 (4)	1.3333 (4)	0.4321 (4)	0.0503 (8)
C8	−0.0112 (4)	0.8498 (4)	0.1877 (4)	0.0491 (8)
C9	−0.2360 (5)	0.5972 (5)	−0.0216 (4)	0.0692 (10)
H9A	−0.2482	0.5131	−0.1238	0.104*
H9B	−0.3359	0.6639	−0.0462	0.104*
H9C	−0.2474	0.5303	0.0623	0.104*

	U11	U22	U33	U12	U13	U23
F1	0.0579 (11)	0.0628 (13)	0.0540 (10)	−0.0020 (9)	0.0211 (9)	−0.0111 (8)
O1	0.0526 (15)	0.0782 (17)	0.0532 (13)	−0.0072 (11)	0.0119 (10)	0.0038 (11)
O2	0.0590 (16)	0.0765 (18)	0.0690 (15)	−0.0133 (11)	0.0303 (11)	0.0019 (11)
O3	0.0532 (16)	0.088 (2)	0.0828 (17)	−0.0110 (13)	0.0346 (13)	−0.0154 (14)
O4	0.0485 (14)	0.0591 (14)	0.0525 (11)	−0.0015 (10)	0.0137 (10)	−0.0038 (10)
C1	0.0435 (17)	0.0453 (17)	0.0477 (15)	0.0102 (14)	0.0161 (13)	0.0123 (13)
C2	0.0485 (18)	0.0445 (17)	0.0414 (14)	0.0071 (13)	0.0153 (13)	0.0026 (11)
C3	0.0447 (18)	0.051 (2)	0.0470 (15)	0.0086 (14)	0.0202 (13)	0.0045 (13)
C4	0.0431 (17)	0.0430 (16)	0.0434 (15)	0.0074 (13)	0.0149 (13)	0.0091 (11)
C5	0.050 (2)	0.0467 (18)	0.0490 (16)	0.0076 (14)	0.0208 (14)	0.0017 (13)
C6	0.050 (2)	0.056 (2)	0.0535 (17)	0.0099 (15)	0.0243 (14)	0.0063 (14)
C7	0.049 (2)	0.0493 (18)	0.0510 (17)	0.0095 (14)	0.0168 (15)	0.0105 (14)
C8	0.0432 (18)	0.0511 (18)	0.0490 (16)	0.0079 (14)	0.0156 (14)	0.0055 (13)
C9	0.052 (2)	0.062 (2)	0.069 (2)	−0.0055 (17)	0.0060 (16)	−0.0018 (17)

F1—C2	1.364 (3)	C3—C4	1.393 (4)
O1—C7	1.257 (3)	C3—H3A	0.93
O2—C7	1.278 (4)	C4—C5	1.405 (4)
O2—H2A	0.82	C4—C8	1.504 (4)
O3—C8	1.197 (4)	C5—C6	1.384 (4)
O4—C8	1.336 (4)	C5—H5A	0.93
O4—C9	1.460 (4)	C6—H6A	0.93
C1—C2	1.400 (4)	C9—H9A	0.96
C1—C6	1.405 (4)	C9—H9B	0.96
C1—C7	1.504 (4)	C9—H9C	0.96
C2—C3	1.372 (4)
C7—O2—H2A	109.5	C4—C5—H5A	120.0
C8—O4—C9	115.8 (2)	C5—C6—C1	121.4 (3)
C2—C1—C6	116.8 (3)	C5—C6—H6A	119.3
C2—C1—C7	124.1 (3)	C1—C6—H6A	119.3
C6—C1—C7	119.2 (2)	O1—C7—O2	124.2 (3)
F1—C2—C3	117.5 (2)	O1—C7—C1	119.9 (3)
F1—C2—C1	119.5 (3)	O2—C7—C1	115.9 (3)
C3—C2—C1	122.9 (3)	O3—C8—O4	124.0 (3)
C2—C3—C4	119.5 (3)	O3—C8—C4	124.0 (3)
C2—C3—H3A	120.2	O4—C8—C4	112.0 (2)
C4—C3—H3A	120.2	O4—C9—H9A	109.5
C3—C4—C5	119.4 (3)	O4—C9—H9B	109.5
C3—C4—C8	117.9 (2)	H9A—C9—H9B	109.5
C5—C4—C8	122.7 (3)	O4—C9—H9C	109.5
C6—C5—C4	120.0 (3)	H9A—C9—H9C	109.5
C6—C5—H5A	120.0	H9B—C9—H9C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···F1i	0.96	2.54	3.278 (5)	134 (1)
O2ii—H2Aii···O1	0.82	1.86	2.672 (4)	170 (1)
C3—H3A···O3iii	0.93	2.53	3.325 (4)	144 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯F1i	0.96	2.54	3.278 (5)	134 (1)
O2ii—H2Aii⋯O1	0.82	1.86	2.672 (4)	170 (1)
C3—H3A⋯O3iii	0.93	2.53	3.325 (4)	144 (1)

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