Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803007700/na6219sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803007700/na6219Isup2.hkl |
CCDC reference: 214619
Key indicators
- Single-crystal X-ray study
- T = 190 K
- Mean (C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.100
- Data-to-parameter ratio = 13.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
A crystal of suitable quality for single-crystal X-ray diffraction was obtained from the sample supplied by Fluorochem. The synthesis of the title compound has been described by Haszeldine (1957).
H atoms refined isotropically; C—H distances were in the range 0.88 (2)–0.92 (2) Å and O—H distances were 0.91 (3) and 1.07 (4) Å.
Data collection: COLLECT (Nonius, 1997-2001); cell refinement: DENZO/SCALEPACK; data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1996); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 2001); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.
Fig. 1. Crystallographic diagram of the asymmetric unit with atomic numbering. Displacement ellipsoids are drawn at the 50% probability level. H atoms were isotropically refined. |
C4H3F3O2 | F(000) = 560.000 |
Mr = 140.06 | Dx = 1.727 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.8280 (2) Å | Cell parameters from 2437 reflections |
b = 9.8064 (2) Å | θ = 5–27° |
c = 10.1768 (2) Å | µ = 0.20 mm−1 |
β = 94.307 (1)° | T = 190 K |
V = 1077.56 (4) Å3 | Plate, colourless |
Z = 8 | 0.30 × 0.30 × 0.15 mm |
Nonius KappaCCD diffractometer | 1961 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.01 |
ω scans | θmax = 27.5°, θmin = 5.3° |
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1996) | h = −14→14 |
Tmin = 0.94, Tmax = 0.97 | k = −12→12 |
4700 measured reflections | l = −13→13 |
2429 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | All H-atom parameters refined |
wR(F2) = 0.100 | Method = SHELXL 97 (Sheldrick, 1997)
W = q / [Sigma2(F*) + (P(1)p)2 + P(2)p + P(4) + P(5)Sin(theta)]
where the parameter values are: P(1) = 0.388E-01 P(2) = 0.474 P(3) = 0.00 P(4) = 0.00 P(5) = 0.00 P(6) = 0.333 |
S = 0.99 | (Δ/σ)max = 0.001 |
2429 reflections | Δρmax = 0.35 e Å−3 |
187 parameters | Δρmin = −0.31 e Å−3 |
C4H3F3O2 | V = 1077.56 (4) Å3 |
Mr = 140.06 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.8280 (2) Å | µ = 0.20 mm−1 |
b = 9.8064 (2) Å | T = 190 K |
c = 10.1768 (2) Å | 0.30 × 0.30 × 0.15 mm |
β = 94.307 (1)° |
Nonius KappaCCD diffractometer | 2429 independent reflections |
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1996) | 1961 reflections with I > 2σ(I) |
Tmin = 0.94, Tmax = 0.97 | Rint = 0.01 |
4700 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 187 parameters |
wR(F2) = 0.100 | All H-atom parameters refined |
S = 0.99 | Δρmax = 0.35 e Å−3 |
2429 reflections | Δρmin = −0.31 e Å−3 |
x | y | z | Uiso*/Ueq | ||
H1 | 0.563 (3) | 0.460 (3) | 0.630 (3) | 0.120 (11)* | |
H101 | 0.597 (4) | 0.251 (5) | 0.729 (4) | 0.180 (17)* | |
H4 | 0.7626 (17) | 0.462 (2) | 0.3976 (19) | 0.047 (5)* | |
H5 | 0.8898 (17) | 0.234 (2) | 0.4887 (19) | 0.049 (5)* | |
H104 | 0.3885 (17) | 0.236 (2) | 0.9734 (19) | 0.050 (5)* | |
H105 | 0.3054 (19) | 0.501 (2) | 0.922 (2) | 0.056 (6)* | |
O101 | 0.53815 (11) | 0.23484 (12) | 0.80720 (11) | 0.0447 | |
O102 | 0.45402 (11) | 0.43519 (12) | 0.74780 (12) | 0.0466 | |
C103 | 0.46243 (12) | 0.33352 (14) | 0.82018 (14) | 0.0309 | |
C104 | 0.38178 (13) | 0.31879 (16) | 0.93103 (15) | 0.0333 | |
C105 | 0.30911 (13) | 0.41773 (16) | 0.96377 (14) | 0.0328 | |
C106 | 0.22768 (14) | 0.40758 (17) | 1.07472 (15) | 0.0376 | |
F107 | 0.10915 (8) | 0.42248 (13) | 1.0338 (1) | 0.0576 | |
F108 | 0.25210 (11) | 0.50736 (14) | 1.16249 (11) | 0.0690 | |
F109 | 0.2384 (1) | 0.29041 (13) | 1.13908 (11) | 0.0642 | |
O1 | 0.6191 (1) | 0.47338 (11) | 0.56840 (11) | 0.0378 | |
O2 | 0.6886 (1) | 0.26251 (11) | 0.61478 (11) | 0.0409 | |
C3 | 0.69059 (12) | 0.37175 (15) | 0.55196 (13) | 0.0303 | |
C4 | 0.77927 (14) | 0.39228 (16) | 0.44974 (14) | 0.0331 | |
C5 | 0.87336 (13) | 0.31024 (16) | 0.43697 (14) | 0.0333 | |
C6 | 0.96348 (14) | 0.33095 (17) | 0.33542 (16) | 0.0402 | |
F7 | 0.9771 (1) | 0.21884 (11) | 0.26449 (11) | 0.0577 | |
F8 | 1.07577 (9) | 0.36174 (14) | 0.38947 (12) | 0.0685 | |
F9 | 0.93024 (11) | 0.42947 (12) | 0.25017 (11) | 0.0647 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O101 | 0.0485 (6) | 0.0412 (6) | 0.0468 (6) | 0.0159 (5) | 0.0200 (5) | 0.0066 (5) |
O102 | 0.0470 (6) | 0.0441 (7) | 0.0515 (7) | 0.0114 (5) | 0.0217 (5) | 0.0194 (5) |
C103 | 0.0305 (7) | 0.0296 (7) | 0.0334 (7) | 0.0020 (5) | 0.0075 (5) | 0.0018 (6) |
C104 | 0.0343 (7) | 0.0320 (7) | 0.0347 (7) | 0.0014 (6) | 0.0097 (6) | 0.0053 (6) |
C105 | 0.0321 (7) | 0.0345 (8) | 0.0325 (7) | 0.0015 (6) | 0.0069 (5) | 0.0026 (6) |
C106 | 0.0331 (7) | 0.0464 (9) | 0.0340 (7) | 0.0052 (6) | 0.0073 (6) | −0.0005 (7) |
F107 | 0.0310 (5) | 0.0887 (8) | 0.0544 (6) | 0.0097 (5) | 0.0103 (4) | 0.0021 (6) |
F108 | 0.0706 (7) | 0.0885 (9) | 0.0500 (6) | −0.0061 (6) | 0.0170 (5) | −0.0311 (6) |
F109 | 0.0661 (7) | 0.0715 (8) | 0.0595 (7) | 0.0203 (6) | 0.0341 (5) | 0.0303 (6) |
O1 | 0.0375 (6) | 0.0387 (6) | 0.0385 (6) | 0.0088 (4) | 0.0113 (4) | 0.0020 (5) |
O2 | 0.0504 (6) | 0.0344 (6) | 0.0402 (6) | 0.0055 (5) | 0.0187 (5) | 0.0061 (5) |
C3 | 0.0300 (7) | 0.0331 (7) | 0.0280 (7) | 0.0016 (5) | 0.0038 (5) | −0.0010 (6) |
C4 | 0.0357 (7) | 0.0347 (8) | 0.0296 (7) | −0.0000 (6) | 0.0072 (5) | 0.0025 (6) |
C5 | 0.0338 (7) | 0.0355 (8) | 0.0314 (7) | −0.0014 (6) | 0.0076 (6) | 0.0004 (6) |
C6 | 0.0370 (8) | 0.0442 (9) | 0.0408 (8) | −0.0011 (7) | 0.0131 (6) | −0.0007 (7) |
F7 | 0.0624 (7) | 0.0589 (7) | 0.0555 (6) | 0.0018 (5) | 0.0288 (5) | −0.0139 (5) |
F8 | 0.0372 (6) | 0.098 (1) | 0.0721 (8) | −0.0191 (6) | 0.0156 (5) | −0.0146 (7) |
F9 | 0.0720 (7) | 0.0632 (7) | 0.0637 (7) | 0.0109 (6) | 0.0376 (6) | 0.0247 (6) |
H1—O1 | 0.91 (3) | C106—F107 | 1.327 (2) |
H101—O101 | 1.07 (4) | C106—F108 | 1.338 (2) |
H4—C4 | 0.88 (2) | C106—F109 | 1.323 (2) |
H5—C5 | 0.92 (2) | O1—C3 | 1.281 (2) |
H104—C104 | 0.92 (2) | O2—C3 | 1.249 (2) |
H105—C105 | 0.92 (2) | C3—C4 | 1.482 (2) |
O101—C103 | 1.282 (2) | C4—C5 | 1.312 (2) |
O102—C103 | 1.239 (2) | C5—C6 | 1.488 (2) |
C103—C104 | 1.485 (2) | C6—F7 | 1.329 (2) |
C104—C105 | 1.308 (2) | C6—F8 | 1.331 (2) |
C105—C106 | 1.487 (2) | C6—F9 | 1.330 (2) |
H101—O101—C103 | 113 (2) | H1—O1—C3 | 115 (2) |
O101—C103—O102 | 124.4 (1) | O1—C3—O2 | 124.5 (1) |
O101—C103—C104 | 115.0 (1) | O1—C3—C4 | 114.6 (1) |
O102—C103—C104 | 120.6 (1) | O2—C3—C4 | 120.9 (1) |
H104—C104—C103 | 114.3 (10) | H4—C4—C3 | 114.5 (10) |
H104—C104—C105 | 124.3 (10) | H4—C4—C5 | 123.1 (10) |
C103—C104—C105 | 121.4 (1) | C3—C4—C5 | 122.4 (1) |
H105—C105—C104 | 122.9 (10) | H5—C5—C4 | 123.8 (10) |
H105—C105—C106 | 114.0 (10) | H5—C5—C6 | 113.5 (10) |
C104—C105—C106 | 123.1 (1) | C4—C5—C6 | 122.7 (2) |
C105—C106—F107 | 111.7 (1) | C5—C6—F7 | 111.7 (1) |
C105—C106—F108 | 111.0 (1) | C5—C6—F8 | 111.7 (1) |
F107—C106—F108 | 105.5 (1) | F7—C6—F8 | 106.1 (1) |
C105—C106—F109 | 113.5 (1) | C5—C6—F9 | 113.1 (1) |
F107—C106—F109 | 107.3 (1) | F7—C6—F9 | 106.4 (1) |
F108—C106—F109 | 107.4 (1) | F8—C6—F9 | 107.4 (1) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O102 | 0.92 (3) | 1.76 (3) | 2.676 (2) | 179 (3) |
O101—H101···O2 | 1.07 (4) | 1.59 (4) | 2.654 (2) | 175 (4) |
Experimental details
Crystal data | |
Chemical formula | C4H3F3O2 |
Mr | 140.06 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 190 |
a, b, c (Å) | 10.8280 (2), 9.8064 (2), 10.1768 (2) |
β (°) | 94.307 (1) |
V (Å3) | 1077.56 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.30 × 0.30 × 0.15 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1996) |
Tmin, Tmax | 0.94, 0.97 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4700, 2429, 1961 |
Rint | 0.01 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.100, 0.99 |
No. of reflections | 2429 |
No. of parameters | 187 |
No. of restraints | ? |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.35, −0.31 |
Computer programs: COLLECT (Nonius, 1997-2001), DENZO/SCALEPACK (Otwinowski & Minor, 1996), SIR92 (Altomare et al., 1994), CRYSTALS (Watkin et al., 2001), CAMERON (Watkin et al., 1996), CRYSTALS.
O101—C103 | 1.282 (2) | O1—C3 | 1.281 (2) |
O102—C103 | 1.239 (2) | O2—C3 | 1.249 (2) |
C103—C104 | 1.485 (2) | C3—C4 | 1.482 (2) |
C104—C105 | 1.308 (2) | C4—C5 | 1.312 (2) |
C105—C106 | 1.487 (2) | C5—C6 | 1.488 (2) |
C106—F107 | 1.327 (2) | C6—F7 | 1.329 (2) |
C106—F108 | 1.338 (2) | C6—F8 | 1.331 (2) |
C106—F109 | 1.323 (2) | C6—F9 | 1.330 (2) |
O101—C103—O102 | 124.4 (1) | O1—C3—O2 | 124.5 (1) |
O101—C103—C104 | 115.0 (1) | O1—C3—C4 | 114.6 (1) |
O102—C103—C104 | 120.6 (1) | O2—C3—C4 | 120.9 (1) |
C103—C104—C105 | 121.4 (1) | C3—C4—C5 | 122.4 (1) |
C104—C105—C106 | 123.1 (1) | C4—C5—C6 | 122.7 (2) |
C105—C106—F107 | 111.7 (1) | C5—C6—F7 | 111.7 (1) |
C105—C106—F108 | 111.0 (1) | C5—C6—F8 | 111.7 (1) |
F107—C106—F108 | 105.5 (1) | F7—C6—F8 | 106.1 (1) |
C105—C106—F109 | 113.5 (1) | C5—C6—F9 | 113.1 (1) |
F107—C106—F109 | 107.3 (1) | F7—C6—F9 | 106.4 (1) |
F108—C106—F109 | 107.4 (1) | F8—C6—F9 | 107.4 (1) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O102 | 0.92 (3) | 1.76 (3) | 2.676 (2) | 179 (3) |
O101—H101···O2 | 1.07 (4) | 1.59 (4) | 2.654 (2) | 175 (4) |
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The structure of the title compound, (I), was determined as part of a study into the polymorphic forms of the related compound tetrolic acid and an investigation into the structures preferentially formed by small compounds with a single carboxylic acid moiety. Compounds with a double bond α to the C atom of the carboxylic acid group have a strong tendency to form dimers. This compound is no exception, crystallizing in the space group P21/c. The two molecules forming the dimer have a non-crystallographic centre of symmetry between the carboxylic acid groups [at x = 0.586 (3), y = 0.360 (3) z = 0.696 (3)]. This can be contrasted with the structure of crotonic acid (Shimizu et al., 1974), which utilizes the crystallographic centre of symmetry to form the dimer. The hydrogen-bonded dimers form ribbons through close contacts involving the F atoms (F···F distances of 3.0, 3.3 and 3.4 Å), and the ribbons lie side-by-side to form sheets. [Please provide correct chemical diagram showing F atoms]