5-Fluoro-isophthalic acid.

In the crystal structure of the title compound, C(8)H(5)FO(4), the complete molecule is generated by crystallographic twofold symmetry with two C atoms and the F atom lying on the axis. The mol-ecule is almost planar with the carboxyl group twisted with respect to the mean plane of the benzene ring by a dihedral angle of 2.01 (1)°. In the crystal, inter-molecular O-H⋯O hydrogen bonds and C-H⋯F inter-actions connect the mol-ecules into a two-dimensional supra-molecular array.

Related literature

For isophthalic acid, see: Bhogala et al. (2005 ▶); Derissen (1974 ▶). For the use of the title compound in crystal engin­eering, see: Zhang et al. (2010 ▶).

Experimental

Crystal data

C8H5FO4

M = 184.12

Monoclinic,

a = 3.7736 (8) Å

b = 16.292 (4) Å

c = 6.2753 (14) Å

β = 91.871 (5)°

V = 385.60 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.14 mm−1

T = 297 K

0.22 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.969, T max = 0.979

2201 measured reflections

743 independent reflections

603 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.161

S = 1.04

743 reflections

64 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 2005 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004004/go2002sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004004/go2002Isup2.hkl

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

C8H5FO4	F(000) = 188
Mr = 184.12	Dx = 1.586 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 1020 reflections
a = 3.7736 (8) Å	θ = 2.5–28.0°
b = 16.292 (4) Å	µ = 0.14 mm−1
c = 6.2753 (14) Å	T = 297 K
β = 91.871 (5)°	Block, colourless
V = 385.60 (14) Å3	0.22 × 0.20 × 0.15 mm
Z = 2

Bruker APEXII CCD diffractometer	743 independent reflections
Radiation source: fine-focus sealed tube	603 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −4→4
Tmin = 0.969, Tmax = 0.979	k = −17→19
2201 measured reflections	l = −7→5

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1244P)2] where P = (Fo2 + 2Fc2)/3
743 reflections	(Δ/σ)max < 0.001
64 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.6268 (4)	0.59855 (9)	0.8588 (3)	0.0524 (5)
C2	0.7105 (4)	0.67633 (9)	0.7484 (2)	0.0487 (5)
C3	0.8602 (4)	0.67563 (10)	0.5486 (3)	0.0529 (5)
H3	0.9107	0.6265	0.4806	0.063*
C4	0.9312 (5)	0.7500	0.4549 (3)	0.0540 (6)
C5	0.6370 (5)	0.7500	0.8476 (3)	0.0477 (6)
H5	0.5379	0.7500	0.9813	0.057*
F1	1.0787 (4)	0.7500	0.2629 (2)	0.0744 (6)
O1	0.7073 (4)	0.53205 (8)	0.7622 (2)	0.0775 (6)
H1	0.6348	0.4905	0.8205	0.116*
O2	0.4837 (4)	0.60037 (7)	1.0328 (2)	0.0722 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0490 (9)	0.0612 (10)	0.0474 (10)	−0.0023 (6)	0.0088 (7)	−0.0080 (7)
C2	0.0385 (8)	0.0652 (11)	0.0424 (9)	−0.0012 (6)	0.0022 (6)	−0.0051 (6)
C3	0.0420 (9)	0.0726 (12)	0.0441 (10)	−0.0006 (6)	0.0027 (7)	−0.0087 (7)
C4	0.0426 (11)	0.0852 (16)	0.0346 (11)	0.000	0.0069 (9)	0.000
C5	0.0400 (10)	0.0642 (14)	0.0395 (11)	0.000	0.0072 (8)	0.000
F1	0.0745 (10)	0.1105 (12)	0.0393 (8)	0.000	0.0190 (7)	0.000
O1	0.1022 (11)	0.0610 (8)	0.0715 (10)	−0.0050 (6)	0.0359 (8)	−0.0121 (6)
O2	0.0938 (10)	0.0622 (9)	0.0628 (9)	−0.0038 (6)	0.0355 (7)	−0.0032 (5)

C1—O2	1.235 (2)	C3—H3	0.9300
C1—O1	1.2826 (19)	C4—F1	1.343 (2)
C1—C2	1.483 (2)	C4—C3i	1.377 (2)
C2—C5	1.3841 (18)	C5—C2i	1.3841 (19)
C2—C3	1.392 (2)	C5—H5	0.9300
C3—C4	1.377 (2)	O1—H1	0.8201
O2—C1—O1	123.73 (15)	C2—C3—H3	121.1
O2—C1—C2	119.91 (13)	F1—C4—C3	118.37 (11)
O1—C1—C2	116.35 (15)	F1—C4—C3i	118.36 (11)
C5—C2—C3	120.34 (15)	C3—C4—C3i	123.3 (2)
C5—C2—C1	118.83 (15)	C2—C5—C2i	120.3 (2)
C3—C2—C1	120.83 (14)	C2—C5—H5	119.9
C4—C3—C2	117.89 (16)	C2i—C5—H5	119.9
C4—C3—H3	121.1	C1—O1—H1	113.5
O2—C1—C2—C5	2.3 (3)	C1—C2—C3—C4	179.97 (14)
O1—C1—C2—C5	−178.51 (16)	C2—C3—C4—F1	179.40 (14)
O2—C1—C2—C3	−177.68 (14)	C2—C3—C4—C3i	−0.3 (3)
O1—C1—C2—C3	1.5 (3)	C3—C2—C5—C2i	0.3 (3)
C5—C2—C3—C4	0.0 (3)	C1—C2—C5—C2i	−179.72 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ii	0.82	1.81	2.625 (2)	174
C5—H5···F1iii	0.93	2.52	3.404 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.81	2.625 (2)	174
C5—H5⋯F1ii	0.93	2.52	3.404 (2)	160

Symmetry codes: (i) ; (ii) .