2-Carbamoyl-3,4,5,6-tetra-fluoro-benzoic acid.

In the title compound, C(8)H(3)F(4)NO(3), the carb-oxy group lies nearly in the plane of the ring with a C-C-C-O torsion angle of -10.5 (4)°. The carbamoyl group is almost perpendic-ular to the benzene ring [C-C-C-O torsion angle = 82.2 (4) °]. In the crystal, molecules are linked via O-H⋯O and N-H⋯O hydrogen bonds involving the carbamoyl and carb-oxy groups.

Related literature

For general background to the title compound and its preparation, see: Xu et al. (2008 ▶); Li et al. (1999 ▶); Poshkus & Herweh (1957 ▶); Cai et al. (1992 ▶); Lee et al. (2005 ▶); Guo et al. (2011 ▶); Liao et al. (2011 ▶).

Experimental

Crystal data

C8H3F4NO3

M = 237.11

Monoclinic,

a = 14.5872 (6) Å

b = 6.9193 (3) Å

c = 8.6129 (4) Å

β = 100.086 (4)°

V = 855.89 (7) Å3

Z = 4

Cu Kα radiation

μ = 1.78 mm−1

T = 268 K

0.42 × 0.31 × 0.17 mm

Data collection

Agilent Xcalibur Gemini ultra Sapphire-3 CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.643, T max = 1.000

2346 measured reflections

1312 independent reflections

1240 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.091

S = 1.14

1312 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036549/rk2367sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036549/rk2367Isup2.hkl

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

C8H3F4NO3	F(000) = 472
Mr = 237.11	Dx = 1.840 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
a = 14.5872 (6) Å	Cell parameters from 1702 reflections
b = 6.9193 (3) Å	θ = 5.2–62.6°
c = 8.6129 (4) Å	µ = 1.78 mm−1
β = 100.086 (4)°	T = 268 K
V = 855.89 (7) Å3	Block, colourless
Z = 4	0.42 × 0.31 × 0.17 mm

Agilent Xcalibur Gemini ultra Sapphire-3 CCD diffractometer	1312 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1240 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.013
Detector resolution: 16.0288 pixels mm-1	θmax = 62.7°, θmin = 7.1°
ω scans	h = −15→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −4→7
Tmin = 0.643, Tmax = 1.000	l = −9→9
2346 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.5536P] where P = (Fo2 + 2Fc2)/3
1312 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Experimental. Absorption correction: CrysAlisPro (Agilent Technologies, 2011); Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.27285 (8)	0.04074 (16)	0.69216 (13)	0.0293 (3)
F4	0.11543 (8)	0.66145 (18)	0.36824 (14)	0.0328 (3)
F2	0.09507 (9)	0.02888 (19)	0.54379 (17)	0.0416 (4)
O3	0.39455 (9)	0.41810 (19)	0.84775 (14)	0.0219 (3)
F3	0.01714 (8)	0.3444 (2)	0.38240 (16)	0.0394 (4)
O1	0.27710 (9)	0.8186 (2)	0.40108 (15)	0.0253 (4)
H1	0.3157	0.9023	0.3929	0.038*
O2	0.39129 (9)	0.7021 (2)	0.58320 (16)	0.0280 (4)
N1	0.45248 (11)	0.2650 (2)	0.65574 (18)	0.0234 (4)
H1A	0.5059	0.2493	0.7150	0.028*
H1B	0.4431	0.2227	0.5604	0.028*
C1	0.25134 (12)	0.5238 (3)	0.5229 (2)	0.0182 (4)
C5	0.23637 (13)	0.1978 (3)	0.6119 (2)	0.0213 (4)
C6	0.29012 (12)	0.3598 (3)	0.6086 (2)	0.0173 (4)
C4	0.14478 (14)	0.1886 (3)	0.5367 (2)	0.0266 (5)
C3	0.10574 (13)	0.3486 (3)	0.4559 (2)	0.0259 (5)
C8	0.31341 (12)	0.6916 (3)	0.5074 (2)	0.0182 (4)
C2	0.15862 (13)	0.5134 (3)	0.4498 (2)	0.0223 (4)
C7	0.38555 (12)	0.3533 (3)	0.7106 (2)	0.0174 (4)

	U11	U22	U33	U12	U13	U23
F1	0.0368 (7)	0.0204 (6)	0.0312 (6)	0.0008 (5)	0.0074 (5)	0.0066 (5)
F4	0.0216 (6)	0.0325 (7)	0.0399 (7)	0.0031 (5)	−0.0069 (5)	0.0090 (5)
F2	0.0326 (7)	0.0308 (7)	0.0608 (9)	−0.0166 (6)	0.0066 (6)	0.0017 (6)
O3	0.0257 (7)	0.0245 (7)	0.0145 (7)	0.0056 (6)	0.0007 (5)	−0.0019 (5)
F3	0.0163 (6)	0.0463 (8)	0.0514 (8)	−0.0076 (5)	−0.0056 (5)	−0.0016 (6)
O1	0.0235 (7)	0.0248 (8)	0.0254 (7)	−0.0043 (6)	−0.0017 (6)	0.0084 (6)
O2	0.0205 (7)	0.0282 (8)	0.0318 (8)	−0.0053 (6)	−0.0053 (6)	0.0070 (6)
N1	0.0191 (8)	0.0329 (10)	0.0168 (8)	0.0069 (7)	−0.0009 (6)	−0.0051 (7)
C1	0.0191 (9)	0.0204 (10)	0.0153 (9)	0.0009 (7)	0.0036 (7)	−0.0015 (7)
C5	0.0257 (10)	0.0190 (10)	0.0203 (9)	0.0030 (8)	0.0068 (8)	0.0016 (7)
C6	0.0186 (9)	0.0200 (10)	0.0140 (8)	0.0013 (7)	0.0052 (7)	−0.0020 (7)
C4	0.0237 (10)	0.0265 (11)	0.0312 (11)	−0.0084 (8)	0.0090 (8)	−0.0043 (9)
C3	0.0153 (9)	0.0326 (12)	0.0288 (10)	−0.0020 (8)	0.0013 (8)	−0.0046 (9)
C8	0.0191 (9)	0.0198 (10)	0.0150 (9)	0.0012 (7)	0.0015 (7)	−0.0004 (7)
C2	0.0187 (9)	0.0262 (11)	0.0208 (9)	0.0036 (8)	0.0004 (7)	0.0014 (8)
C7	0.0213 (9)	0.0157 (9)	0.0153 (9)	0.0004 (7)	0.0032 (7)	0.0023 (7)

F1—C5	1.346 (2)	N1—C7	1.308 (2)
F4—C2	1.336 (2)	C1—C6	1.416 (3)
F2—C4	1.329 (2)	C1—C8	1.493 (3)
O3—C7	1.249 (2)	C1—C2	1.390 (3)
F3—C3	1.336 (2)	C5—C6	1.371 (3)
O1—H1	0.8200	C5—C4	1.380 (3)
O1—C8	1.312 (2)	C6—C7	1.511 (2)
O2—C8	1.209 (2)	C4—C3	1.377 (3)
N1—H1A	0.8600	C3—C2	1.383 (3)
N1—H1B	0.8600
C8—O1—H1	109.5	F2—C4—C3	120.74 (17)
H1A—N1—H1B	120.0	C3—C4—C5	118.76 (18)
C7—N1—H1A	120.0	F3—C3—C4	120.14 (18)
C7—N1—H1B	120.0	F3—C3—C2	119.97 (18)
C6—C1—C8	118.48 (16)	C4—C3—C2	119.88 (17)
C2—C1—C6	117.56 (17)	O1—C8—C1	113.98 (15)
C2—C1—C8	123.83 (17)	O2—C8—O1	124.27 (17)
F1—C5—C6	119.64 (16)	O2—C8—C1	121.69 (16)
F1—C5—C4	117.84 (17)	F4—C2—C1	122.02 (17)
C6—C5—C4	122.52 (18)	F4—C2—C3	115.95 (16)
C1—C6—C7	124.76 (16)	C3—C2—C1	122.02 (18)
C5—C6—C1	119.22 (16)	O3—C7—N1	123.22 (17)
C5—C6—C7	115.81 (16)	O3—C7—C6	118.21 (15)
F2—C4—C5	120.50 (18)	N1—C7—C6	118.29 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.82	1.78	2.5965 (18)	172
N1—H1A···O3ii	0.86	2.82	3.281 (2)	116
N1—H1A···O2ii	0.86	2.11	2.940 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.82	1.78	2.5965 (18)	172
N1—H1A⋯O2ii	0.86	2.11	2.940 (2)	161

Symmetry codes: (i) ; (ii) .