organic compounds
2,6-Bis(trifluoromethyl)benzoic acid
aDepartment of Chemistry, Saint Mary's University, 923 Robie Street, Halifax, NS, Canada B3H 3C3
*Correspondence e-mail: jason.masuda@smu.ca
The title compound, C9H4F6O2, contains two molecules in the one of which exhibits disorder in both of its trifluoromethyl groups. The dihedral angles between the benzene ring and the carboxyl group are 71.5 (2) and 99.3 (2)° in the two independent molecules. The compound exhibits a catemeric structure resulting from intermolecular O—H⋯O hydrogen bonding between the carboxyl groups.
Related literature
There is only one example in the literature of a crystallographically characterized benzoic acid with trifluoromethyl groups in the ortho position, namely 2-trifluoromethyl-3-pyrrole benzoic acid (see Faigl et al., 1999). For a recent example of crystal engineering to promote the formation of dimeric or catemeric structures in benzoic acids, see: Moorthy et al. (2002). For synthesis details, see: Dmowski & Piasecka-Macieiewska (1998).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2008); cell SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
10.1107/S1600536809016468/bi2369sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809016468/bi2369Isup2.hkl
The title compound was prepared following the literature methods (Dmowski & Piasecka-Macieiewska, 1998) with a slight modification. The compound crystallized from the oily reaction mixture that remained after acidification of the potassium benzoate salt with concentrated HCl, extraction of the organic components with toluene, drying of the organic fraction with magnesium sulfate and concentration by rotary evaporation.
H atoms were placed in geometrically idealized positions with C—H = 0.93 Å and O—H = 0.82 Å and constrained to ride on the parent atom with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(O). The trifluoromethyl groups belonging to C17 and C18 were modeled with a two-site disorder of the F atoms with refined site occupancy factors of 0.569 (5):0.431 (5) and 0.689 (5):0.311 (5), respectively.
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C9H4F6O2 | F(000) = 1024 |
Mr = 258.12 | Dx = 1.738 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6970 reflections |
a = 10.873 (2) Å | θ = 2.3–28.0° |
b = 15.755 (3) Å | µ = 0.20 mm−1 |
c = 11.561 (2) Å | T = 296 K |
β = 94.961 (2)° | Block, colorless |
V = 1973.0 (6) Å3 | 0.39 × 0.31 × 0.26 mm |
Z = 8 |
Bruker APEXII CCD diffractometer | 3438 independent reflections |
Radiation source: fine-focus sealed tube | 2889 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −12→12 |
Tmin = 0.834, Tmax = 0.951 | k = −18→18 |
12904 measured reflections | l = −13→11 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.058P)2 + 0.5224P] where P = (Fo2 + 2Fc2)/3 |
3438 reflections | (Δ/σ)max < 0.001 |
331 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C9H4F6O2 | V = 1973.0 (6) Å3 |
Mr = 258.12 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.873 (2) Å | µ = 0.20 mm−1 |
b = 15.755 (3) Å | T = 296 K |
c = 11.561 (2) Å | 0.39 × 0.31 × 0.26 mm |
β = 94.961 (2)° |
Bruker APEXII CCD diffractometer | 3438 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 2889 reflections with I > 2σ(I) |
Tmin = 0.834, Tmax = 0.951 | Rint = 0.021 |
12904 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.21 e Å−3 |
3438 reflections | Δρmin = −0.23 e Å−3 |
331 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.25273 (16) | 0.14562 (11) | 0.00186 (14) | 0.0532 (4) | |
C2 | 0.34011 (15) | 0.08652 (10) | 0.07069 (14) | 0.0490 (4) | |
C3 | 0.43893 (16) | 0.11687 (12) | 0.14433 (16) | 0.0564 (4) | |
C4 | 0.51596 (17) | 0.06028 (14) | 0.20807 (17) | 0.0666 (5) | |
H4A | 0.5807 | 0.0808 | 0.2581 | 0.080* | |
C5 | 0.49740 (19) | −0.02557 (14) | 0.19783 (18) | 0.0689 (5) | |
H5A | 0.5498 | −0.0629 | 0.2405 | 0.083* | |
C6 | 0.40178 (18) | −0.05640 (12) | 0.12489 (16) | 0.0614 (5) | |
H6A | 0.3900 | −0.1147 | 0.1175 | 0.074* | |
C7 | 0.32257 (15) | −0.00131 (10) | 0.06209 (14) | 0.0508 (4) | |
C8 | 0.46743 (19) | 0.20978 (14) | 0.1562 (2) | 0.0756 (6) | |
F1 | 0.5244 (2) | 0.22865 (11) | 0.25885 (18) | 0.1361 (7) | |
F2 | 0.53907 (15) | 0.23619 (9) | 0.07602 (19) | 0.1232 (7) | |
F3 | 0.36850 (12) | 0.25931 (8) | 0.14440 (14) | 0.0893 (4) | |
C9 | 0.21830 (18) | −0.03876 (12) | −0.01534 (17) | 0.0632 (5) | |
F4 | 0.11518 (12) | −0.04286 (10) | 0.03733 (13) | 0.0975 (4) | |
F5 | 0.19338 (14) | 0.00483 (8) | −0.11254 (11) | 0.0911 (4) | |
F6 | 0.24344 (13) | −0.11707 (8) | −0.04877 (12) | 0.0906 (4) | |
C10 | 0.10257 (17) | 0.15284 (11) | 0.30263 (15) | 0.0545 (4) | |
C11 | 0.07034 (16) | 0.13002 (10) | 0.42282 (14) | 0.0514 (4) | |
C12 | −0.04150 (17) | 0.15569 (11) | 0.46310 (15) | 0.0561 (4) | |
C13 | −0.0643 (2) | 0.14110 (13) | 0.57757 (18) | 0.0711 (5) | |
H13A | −0.1380 | 0.1593 | 0.6045 | 0.085* | |
C14 | 0.0220 (2) | 0.09977 (15) | 0.65140 (18) | 0.0801 (6) | |
H14A | 0.0066 | 0.0906 | 0.7283 | 0.096* | |
C15 | 0.1301 (2) | 0.07212 (14) | 0.61252 (17) | 0.0730 (6) | |
H15A | 0.1869 | 0.0430 | 0.6626 | 0.088* | |
C16 | 0.15558 (18) | 0.08709 (12) | 0.49899 (16) | 0.0603 (5) | |
O1 | 0.14736 (11) | 0.15753 (8) | 0.02411 (10) | 0.0606 (3) | |
O2 | 0.30404 (14) | 0.18036 (9) | −0.08444 (12) | 0.0751 (4) | |
H2A | 0.2549 | 0.2129 | −0.1192 | 0.113* | |
O3 | 0.05615 (13) | 0.10397 (9) | 0.22093 (11) | 0.0684 (4) | |
H3A | 0.0818 | 0.1182 | 0.1592 | 0.103* | |
O4 | 0.16936 (19) | 0.21110 (11) | 0.28586 (13) | 0.0999 (6) | |
C17 | −0.13950 (10) | 0.19782 (8) | 0.38373 (10) | 0.0726 (5) | |
F7A | −0.09321 (12) | 0.25255 (8) | 0.31618 (10) | 0.1010 (13) | 0.569 (5) |
F8A | −0.19164 (10) | 0.13805 (10) | 0.31178 (10) | 0.0901 (11) | 0.569 (5) |
F9A | −0.22489 (10) | 0.23045 (8) | 0.43893 (12) | 0.139 (2) | 0.569 (5) |
F7B | −0.17175 (10) | 0.16347 (9) | 0.28614 (11) | 0.144 (3) | 0.431 (5) |
F9B | −0.10986 (11) | 0.28028 (10) | 0.35381 (9) | 0.1164 (19) | 0.431 (5) |
F8B | −0.24254 (11) | 0.21614 (8) | 0.43317 (12) | 0.0970 (19) | 0.431 (5) |
C18 | 0.27540 (10) | 0.05569 (8) | 0.46034 (11) | 0.0751 (6) | |
F10A | 0.26369 (10) | 0.01894 (8) | 0.35789 (13) | 0.0877 (11) | 0.689 (5) |
F11A | 0.36230 (10) | 0.11205 (10) | 0.46284 (11) | 0.1163 (14) | 0.689 (5) |
F12A | 0.32020 (9) | −0.01015 (9) | 0.52898 (13) | 0.1142 (11) | 0.689 (5) |
F10B | 0.33236 (9) | 0.12165 (10) | 0.40107 (11) | 0.108 (2) | 0.311 (5) |
F12B | 0.35672 (10) | 0.03614 (8) | 0.54011 (13) | 0.125 (3) | 0.311 (5) |
F11B | 0.26173 (10) | 0.00490 (9) | 0.37781 (12) | 0.154 (5) | 0.311 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0618 (10) | 0.0542 (9) | 0.0442 (9) | 0.0104 (7) | 0.0085 (7) | 0.0040 (7) |
C2 | 0.0497 (8) | 0.0552 (9) | 0.0428 (8) | 0.0073 (7) | 0.0077 (7) | 0.0041 (7) |
C3 | 0.0508 (9) | 0.0623 (10) | 0.0566 (10) | 0.0011 (8) | 0.0089 (8) | −0.0018 (8) |
C4 | 0.0507 (10) | 0.0864 (14) | 0.0607 (11) | 0.0064 (9) | −0.0062 (8) | −0.0020 (10) |
C5 | 0.0631 (11) | 0.0776 (13) | 0.0641 (12) | 0.0199 (10) | −0.0061 (9) | 0.0105 (10) |
C6 | 0.0689 (11) | 0.0567 (10) | 0.0582 (11) | 0.0113 (8) | 0.0025 (9) | 0.0077 (8) |
C7 | 0.0535 (9) | 0.0551 (9) | 0.0436 (9) | 0.0056 (7) | 0.0044 (7) | 0.0031 (7) |
C8 | 0.0608 (11) | 0.0702 (12) | 0.0965 (16) | −0.0044 (10) | 0.0112 (11) | −0.0113 (11) |
F1 | 0.1536 (16) | 0.0987 (11) | 0.1447 (15) | −0.0163 (10) | −0.0518 (13) | −0.0361 (10) |
F2 | 0.1085 (11) | 0.0773 (9) | 0.1956 (19) | −0.0172 (8) | 0.0813 (12) | −0.0035 (10) |
F3 | 0.0828 (8) | 0.0627 (7) | 0.1245 (12) | 0.0037 (6) | 0.0221 (8) | −0.0124 (7) |
C9 | 0.0672 (11) | 0.0597 (11) | 0.0615 (11) | 0.0030 (9) | −0.0013 (9) | 0.0003 (9) |
F4 | 0.0628 (7) | 0.1270 (12) | 0.1024 (10) | −0.0164 (7) | 0.0050 (7) | −0.0162 (9) |
F5 | 0.1201 (11) | 0.0832 (8) | 0.0628 (7) | −0.0013 (7) | −0.0338 (7) | 0.0035 (6) |
F6 | 0.1079 (10) | 0.0632 (7) | 0.0972 (10) | 0.0013 (6) | −0.0118 (8) | −0.0186 (6) |
C10 | 0.0609 (10) | 0.0574 (10) | 0.0454 (9) | −0.0107 (8) | 0.0059 (7) | −0.0075 (7) |
C11 | 0.0640 (10) | 0.0495 (9) | 0.0408 (8) | −0.0136 (7) | 0.0046 (7) | −0.0079 (7) |
C12 | 0.0679 (11) | 0.0526 (9) | 0.0486 (9) | −0.0112 (8) | 0.0089 (8) | −0.0117 (7) |
C13 | 0.0839 (13) | 0.0731 (12) | 0.0591 (12) | −0.0128 (10) | 0.0231 (10) | −0.0126 (10) |
C14 | 0.1122 (18) | 0.0860 (15) | 0.0440 (10) | −0.0135 (13) | 0.0171 (11) | 0.0010 (10) |
C15 | 0.0927 (15) | 0.0781 (13) | 0.0473 (10) | −0.0043 (11) | 0.0009 (10) | 0.0031 (9) |
C16 | 0.0698 (11) | 0.0606 (10) | 0.0499 (10) | −0.0094 (9) | 0.0017 (8) | −0.0042 (8) |
O1 | 0.0575 (7) | 0.0753 (8) | 0.0490 (7) | 0.0156 (6) | 0.0041 (5) | 0.0077 (6) |
O2 | 0.0858 (9) | 0.0756 (9) | 0.0677 (8) | 0.0301 (7) | 0.0294 (7) | 0.0303 (7) |
O3 | 0.0850 (9) | 0.0783 (9) | 0.0420 (6) | −0.0259 (7) | 0.0064 (6) | −0.0103 (6) |
O4 | 0.1505 (15) | 0.0963 (11) | 0.0575 (9) | −0.0706 (11) | 0.0357 (9) | −0.0223 (8) |
C17 | 0.0723 (13) | 0.0783 (14) | 0.0675 (13) | 0.0023 (11) | 0.0087 (10) | −0.0092 (11) |
F7A | 0.115 (2) | 0.088 (2) | 0.099 (2) | 0.0095 (16) | 0.0008 (17) | 0.0347 (18) |
F8A | 0.0718 (17) | 0.0977 (19) | 0.095 (2) | −0.0026 (14) | −0.0251 (14) | −0.0169 (16) |
F9A | 0.153 (4) | 0.144 (3) | 0.121 (4) | 0.087 (3) | 0.022 (3) | −0.030 (3) |
F7B | 0.156 (5) | 0.187 (5) | 0.079 (3) | 0.090 (4) | −0.040 (3) | −0.064 (3) |
F9B | 0.100 (3) | 0.097 (3) | 0.151 (4) | 0.009 (2) | 0.005 (3) | 0.039 (3) |
F8B | 0.055 (2) | 0.146 (4) | 0.092 (4) | 0.006 (3) | 0.018 (2) | 0.007 (3) |
C18 | 0.0736 (13) | 0.0807 (15) | 0.0699 (14) | −0.0014 (11) | 0.0001 (11) | −0.0030 (11) |
F10A | 0.082 (2) | 0.116 (2) | 0.0655 (15) | 0.0210 (16) | 0.0119 (13) | −0.0152 (16) |
F11A | 0.0730 (14) | 0.115 (2) | 0.161 (3) | −0.0229 (14) | 0.0114 (17) | −0.033 (2) |
F12A | 0.1041 (18) | 0.130 (2) | 0.107 (2) | 0.0381 (17) | −0.0002 (15) | 0.0232 (16) |
F10B | 0.076 (3) | 0.109 (4) | 0.146 (6) | 0.006 (3) | 0.039 (3) | 0.029 (4) |
F12B | 0.084 (3) | 0.204 (9) | 0.081 (4) | 0.039 (5) | −0.020 (3) | 0.023 (4) |
F11B | 0.099 (7) | 0.145 (7) | 0.222 (11) | −0.022 (5) | 0.038 (6) | −0.109 (7) |
C1—O1 | 1.210 (2) | C11—C12 | 1.399 (3) |
C1—O2 | 1.305 (2) | C12—C13 | 1.387 (3) |
C1—C2 | 1.507 (2) | C12—C17 | 1.500 (2) |
C2—C3 | 1.396 (2) | C13—C14 | 1.376 (3) |
C2—C7 | 1.399 (2) | C13—H13A | 0.930 |
C3—C4 | 1.390 (3) | C14—C15 | 1.365 (3) |
C3—C8 | 1.500 (3) | C14—H14A | 0.930 |
C4—C5 | 1.371 (3) | C15—C16 | 1.385 (3) |
C4—H4A | 0.930 | C15—H15A | 0.930 |
C5—C6 | 1.370 (3) | C16—C18 | 1.498 (2) |
C5—H5A | 0.930 | O2—H2A | 0.820 |
C6—C7 | 1.383 (2) | O3—H3A | 0.820 |
C6—H6A | 0.930 | C17—F7B | 1.2729 (11) |
C7—C9 | 1.503 (3) | C17—F9A | 1.2791 (11) |
C8—F1 | 1.324 (3) | C17—F7A | 1.2941 (11) |
C8—F3 | 1.326 (3) | C17—F8B | 1.3326 (12) |
C8—F2 | 1.328 (3) | C17—F8A | 1.3485 (12) |
C9—F4 | 1.323 (2) | C17—F9B | 1.3895 (12) |
C9—F5 | 1.325 (2) | C18—F11B | 1.2443 (10) |
C9—F6 | 1.328 (2) | C18—F12B | 1.2593 (11) |
C10—O4 | 1.197 (2) | C18—F11A | 1.2952 (11) |
C10—O3 | 1.287 (2) | C18—F10A | 1.3146 (11) |
C10—C11 | 1.506 (2) | C18—F12A | 1.3697 (11) |
C11—C16 | 1.397 (3) | C18—F10B | 1.4165 (12) |
O1—C1—O2 | 124.93 (16) | C13—C12—C17 | 118.76 (16) |
O1—C1—C2 | 123.28 (15) | C11—C12—C17 | 121.09 (14) |
O2—C1—C2 | 111.78 (14) | C14—C13—C12 | 120.1 (2) |
C3—C2—C7 | 118.36 (15) | C14—C13—H13A | 119.9 |
C3—C2—C1 | 121.80 (15) | C12—C13—H13A | 119.9 |
C7—C2—C1 | 119.84 (15) | C15—C14—C13 | 120.45 (19) |
C4—C3—C2 | 120.00 (17) | C15—C14—H14A | 119.8 |
C4—C3—C8 | 117.85 (18) | C13—C14—H14A | 119.8 |
C2—C3—C8 | 122.14 (17) | C14—C15—C16 | 120.4 (2) |
C5—C4—C3 | 120.63 (18) | C14—C15—H15A | 119.8 |
C5—C4—H4A | 119.7 | C16—C15—H15A | 119.8 |
C3—C4—H4A | 119.7 | C15—C16—C11 | 120.24 (19) |
C6—C5—C4 | 120.08 (17) | C15—C16—C18 | 118.50 (17) |
C6—C5—H5A | 120.0 | C11—C16—C18 | 121.25 (15) |
C4—C5—H5A | 120.0 | C1—O2—H2A | 109.5 |
C5—C6—C7 | 120.36 (18) | C10—O3—H3A | 109.5 |
C5—C6—H6A | 119.8 | F9A—C17—F7A | 111.7 |
C7—C6—H6A | 119.8 | F7B—C17—F8B | 107.2 |
C6—C7—C2 | 120.55 (16) | F9A—C17—F8A | 107.7 |
C6—C7—C9 | 118.00 (16) | F7A—C17—F8A | 104.9 |
C2—C7—C9 | 121.45 (15) | F7B—C17—F9B | 103.2 |
F1—C8—F3 | 105.80 (19) | F8B—C17—F9B | 97.2 |
F1—C8—F2 | 107.3 (2) | F7B—C17—C12 | 118.73 (8) |
F3—C8—F2 | 105.3 (2) | F9A—C17—C12 | 112.38 (8) |
F1—C8—C3 | 112.2 (2) | F7A—C17—C12 | 111.79 (8) |
F3—C8—C3 | 113.92 (17) | F8B—C17—C12 | 114.37 (8) |
F2—C8—C3 | 111.77 (18) | F8A—C17—C12 | 107.87 (8) |
F4—C9—F5 | 107.23 (17) | F9B—C17—C12 | 113.47 (8) |
F4—C9—F6 | 107.01 (17) | F11B—C18—F12B | 115.7 |
F5—C9—F6 | 105.48 (16) | F11A—C18—F10A | 109.6 |
F4—C9—C7 | 111.76 (16) | F11A—C18—F12A | 106.5 |
F5—C9—C7 | 112.95 (16) | F10A—C18—F12A | 101.0 |
F6—C9—C7 | 111.98 (16) | F11B—C18—F10B | 97.4 |
O4—C10—O3 | 123.01 (17) | F12B—C18—F10B | 103.0 |
O4—C10—C11 | 121.71 (15) | F11B—C18—C16 | 113.07 (8) |
O3—C10—C11 | 115.25 (15) | F12B—C18—C16 | 115.85 (8) |
C16—C11—C12 | 118.60 (16) | F11A—C18—C16 | 114.75 (8) |
C16—C11—C10 | 120.19 (16) | F10A—C18—C16 | 113.29 (8) |
C12—C11—C10 | 121.10 (16) | F12A—C18—C16 | 110.63 (9) |
C13—C12—C11 | 120.14 (18) | F10B—C18—C16 | 109.27 (9) |
C7—C2—C1—O1 | 71.5 (2) | C12—C11—C10—O4 | 99.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O4i | 0.82 | 1.82 | 2.6340 (19) | 169 |
O3—H3A···O1 | 0.82 | 1.88 | 2.6951 (18) | 176 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C9H4F6O2 |
Mr | 258.12 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 10.873 (2), 15.755 (3), 11.561 (2) |
β (°) | 94.961 (2) |
V (Å3) | 1973.0 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.39 × 0.31 × 0.26 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.834, 0.951 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12904, 3438, 2889 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.112, 1.02 |
No. of reflections | 3438 |
No. of parameters | 331 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.23 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O4i | 0.82 | 1.82 | 2.6340 (19) | 169.1 |
O3—H3A···O1 | 0.82 | 1.88 | 2.6951 (18) | 175.6 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
Acknowledgements
The authors thank Saint Mary's University for providing funding in the form of initial operating funds (JDM) and student funding through the Summer Employment Experience Program (JMT).
References
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The title molecule crystallizes in a catemer motif, a relatively rare form compared to the typical dimeric motif exhibited by benzoic acids resulting from intermolecular hydrogen bonding between the carboxylic acid groups (Moorthy et al., 2002). The sterically bulky o-CF3 groups result in the carboxylic acid fragments being twisted with respect to the aryl ring. This results in dihedral angles between the aryl ring and carboxylic acid fragments of C7—C2—C1—O1 = 71.5 (2)° and C12—C11—C10—O4 = 99.3 (2)°.