5-Fluoro­salicylic acid

The title compound, C₇H₅FO₃, is nearly planar, and the dihedral angle between the phenyl and carboxyl groups is 4.0 (1)°. There are intramolecular O—H...O and intermol­ecular O—H...O and O—H...F hydrogen bonds, forming ribbons along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.047
• wR factor = 0.111
• Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT431_ALERT_2_C Short Inter HL..A Contact  F1     ..  O2      ..       2.84 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported C7     ..  F1      ..       4.01 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2004); cell refinement: SMART; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-32 for Windows (Farrugia, 1997), POV-RAY for Windows (The POV-RAY Team, 2004) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).

5-Fluorosalicylic Acid

Crystal data

C7H5FO3	F(000) = 320
Mr = 156.11	Dx = 1.589 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2543 reflections
a = 3.8184 (8) Å	θ = 2.6–24.1°
b = 21.219 (4) Å	µ = 0.14 mm^−1
c = 8.2107 (17) Å	T = 293 K
β = 101.172 (4)°	Rod, colourless
V = 652.7 (2) Å^3	0.30 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	1201 independent reflections
Radiation source: fine-focus sealed tube	990 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 25.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −4→4
Tmin = 0.949, Tmax = 0.986	k = −25→25
4794 measured reflections	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	All H-atom parameters refined
S = 1.12	w = 1/[σ^2(Fo^2) + (0.046P)^2 + 0.2148P] where P = (Fo^2 + 2Fc^2)/3
1201 reflections	(Δ/σ)max < 0.001
120 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.0743 (5)	0.87892 (8)	0.24441 (15)	0.0787 (5)
O1	0.4513 (4)	0.99454 (7)	0.76927 (17)	0.0512 (5)
O2	0.2768 (4)	0.93627 (7)	0.96359 (17)	0.0534 (5)
O3	−0.0360 (5)	0.82797 (7)	0.8833 (2)	0.0538 (5)
C1	0.1533 (5)	0.89958 (9)	0.6871 (2)	0.0349 (5)
C2	0.0008 (5)	0.84300 (9)	0.7275 (2)	0.0382 (5)
C3	−0.1188 (6)	0.79951 (10)	0.6032 (3)	0.0450 (6)
C4	−0.0945 (6)	0.81143 (11)	0.4423 (3)	0.0489 (6)
C5	0.0497 (6)	0.86753 (11)	0.4044 (2)	0.0481 (6)
C6	0.1739 (6)	0.91147 (10)	0.5215 (2)	0.0424 (5)
C7	0.2967 (5)	0.94487 (9)	0.8181 (2)	0.0372 (5)
H1O	0.550 (8)	1.0205 (13)	0.862 (4)	0.085 (9)*
H3	−0.226 (6)	0.7626 (11)	0.630 (3)	0.055 (7)*
H3O	0.055 (9)	0.8595 (15)	0.946 (4)	0.103 (12)*
H4	−0.176 (6)	0.7826 (12)	0.356 (3)	0.064 (7)*
H6	0.272 (6)	0.9482 (10)	0.495 (2)	0.040 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.1178 (14)	0.0894 (11)	0.0309 (7)	−0.0283 (10)	0.0196 (8)	−0.0111 (7)
O1	0.0754 (11)	0.0433 (9)	0.0350 (8)	−0.0186 (8)	0.0111 (8)	−0.0052 (7)
O2	0.0814 (12)	0.0486 (9)	0.0306 (9)	−0.0153 (8)	0.0122 (8)	−0.0038 (6)
O3	0.0776 (12)	0.0453 (9)	0.0395 (9)	−0.0120 (8)	0.0140 (8)	0.0047 (7)
C1	0.0375 (11)	0.0342 (10)	0.0326 (11)	0.0039 (8)	0.0056 (8)	−0.0012 (8)
C2	0.0403 (12)	0.0377 (11)	0.0363 (11)	0.0035 (9)	0.0066 (9)	0.0023 (8)
C3	0.0479 (14)	0.0368 (11)	0.0492 (14)	−0.0041 (10)	0.0073 (10)	−0.0034 (10)
C4	0.0524 (14)	0.0484 (13)	0.0439 (13)	−0.0030 (10)	0.0048 (11)	−0.0146 (10)
C5	0.0595 (15)	0.0550 (13)	0.0304 (11)	−0.0022 (11)	0.0102 (10)	−0.0056 (9)
C6	0.0503 (14)	0.0397 (12)	0.0370 (12)	−0.0051 (10)	0.0084 (10)	−0.0002 (9)
C7	0.0432 (12)	0.0358 (10)	0.0322 (11)	0.0017 (9)	0.0063 (9)	0.0007 (8)

Geometric parameters (Å, º)

F1—C5	1.357 (2)	C1—C7	1.467 (3)
O1—C7	1.308 (2)	C2—C3	1.386 (3)
O1—H1O	0.95 (3)	C3—C4	1.366 (3)
O2—C7	1.225 (2)	C3—H3	0.93 (2)
O3—C2	1.352 (2)	C4—C5	1.372 (3)
O3—H3O	0.87 (3)	C4—H4	0.94 (3)
C1—C6	1.400 (3)	C5—C6	1.357 (3)
C1—C2	1.402 (3)	C6—H6	0.91 (2)
C7—O1—H1O	110.7 (16)	C3—C4—H4	122.2 (15)
C2—O3—H3O	106 (2)	C5—C4—H4	118.7 (15)
C6—C1—C2	119.25 (18)	F1—C5—C6	118.9 (2)
C6—C1—C7	120.72 (18)	F1—C5—C4	118.69 (19)
C2—C1—C7	120.02 (17)	C6—C5—C4	122.4 (2)
O3—C2—C3	117.38 (19)	C5—C6—C1	119.1 (2)
O3—C2—C1	123.39 (18)	C5—C6—H6	121.8 (13)
C3—C2—C1	119.23 (19)	C1—C6—H6	119.2 (13)
C4—C3—C2	121.0 (2)	O2—C7—O1	122.39 (18)
C4—C3—H3	120.0 (14)	O2—C7—C1	122.18 (18)
C2—C3—H3	119.0 (14)	O1—C7—C1	115.43 (17)
C3—C4—C5	119.0 (2)
C6—C1—C2—O3	−178.82 (19)	F1—C5—C6—C1	−179.2 (2)
C7—C1—C2—O3	2.6 (3)	C4—C5—C6—C1	−0.3 (4)
C6—C1—C2—C3	1.4 (3)	C2—C1—C6—C5	−0.8 (3)
C7—C1—C2—C3	−177.13 (19)	C7—C1—C6—C5	177.7 (2)
O3—C2—C3—C4	179.3 (2)	C6—C1—C7—O2	178.7 (2)
C1—C2—C3—C4	−0.9 (3)	C2—C1—C7—O2	−2.8 (3)
C2—C3—C4—C5	−0.2 (4)	C6—C1—C7—O1	−2.2 (3)
C3—C4—C5—F1	179.7 (2)	C2—C1—C7—O1	176.29 (18)
C3—C4—C5—C6	0.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2^i	0.96 (3)	1.72 (3)	2.676 (2)	177 (2)
O3—H3O···F1^ii	0.87 (3)	2.47 (3)	3.107 (2)	130 (3)
O3—H3O···O2	0.87 (3)	1.83 (3)	2.615 (2)	149 (3)
C7—O2···F1^ii	1.23 (1)	2.84 (1)	4.010 (2)	159 (1)

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x, y, z+1.