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The molecular structure of the title compound, C
14H
14BrF
3O
2, adopts a bent conformation. Intramolecular O-H
F and intermolecular O-H
O interactions form a bifurcated hydrogen bond which produces a supramolecular assembly of head-to-tail dimers.
Supporting information
CCDC reference: 150739
Cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
Crystal data top
C14H14BrF3O2 | Z = 2 |
Mr = 351.16 | F(000) = 352 |
Triclinic, P1 | Dx = 1.627 Mg m−3 |
a = 7.9539 (16) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5523 (19) Å | Cell parameters from 5354 reflections |
c = 10.695 (2) Å | θ = 2.7–27.5° |
α = 97.61 (3)° | µ = 2.90 mm−1 |
β = 110.44 (3)° | T = 298 K |
γ = 104.17 (3)° | Block, colourless |
V = 716.7 (2) Å3 | 0.35 × 0.35 × 0.35 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 1389 reflections with I > 2σ(I) |
Radiation source: Nonius FR591 rotating anode | Rint = 0.049 |
φ and ω scans to fill Ewald sphere | θmax = 26.0°, θmin = 2.7° |
Absorption correction: multi-scans (Blessing, 1995) | h = −10→10 |
Tmin = 0.331, Tmax = 0.379 | k = −12→12 |
5354 measured reflections | l = −13→13 |
2944 independent reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0791P)2 + 0.1443P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.058 | (Δ/σ)max = 0.002 |
wR(F2) = 0.180 | Δρmax = 0.44 e Å−3 |
S = 1.00 | Δρmin = −0.55 e Å−3 |
2944 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
182 parameters | Extinction coefficient: 0.015 (4) |
0 restraints | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.07811 (11) | 0.90437 (9) | 0.86045 (10) | 0.1296 (5) | |
F1 | 0.7830 (4) | 1.4658 (4) | 0.5278 (3) | 0.0913 (10) | |
F2 | 0.9383 (5) | 1.3107 (4) | 0.5512 (3) | 0.1000 (11) | |
F3 | 1.0410 (4) | 1.5164 (4) | 0.7034 (3) | 0.0863 (9) | |
O1 | 0.9008 (4) | 1.2645 (4) | 0.7862 (3) | 0.0625 (8) | |
H1 | 0.9994 | 1.329 | 0.8383 | 0.094* | |
O2 | 0.7349 (4) | 1.5466 (4) | 1.0032 (3) | 0.0631 (9) | |
C1 | 0.2376 (8) | 0.9932 (6) | 0.7779 (6) | 0.0767 (14) | |
C2 | 0.1812 (7) | 1.0789 (6) | 0.6893 (6) | 0.0820 (15) | |
H2 | 0.0629 | 1.0918 | 0.6675 | 0.098* | |
C3 | 0.3005 (6) | 1.1464 (6) | 0.6320 (5) | 0.0707 (13) | |
H3 | 0.2606 | 1.2045 | 0.5715 | 0.085* | |
C4 | 0.4785 (6) | 1.1304 (5) | 0.6621 (5) | 0.0615 (12) | |
C5 | 0.5295 (7) | 1.0409 (6) | 0.7520 (5) | 0.0728 (13) | |
H5 | 0.6467 | 1.026 | 0.7738 | 0.087* | |
C6 | 0.4128 (8) | 0.9750 (6) | 0.8084 (6) | 0.0811 (15) | |
H6 | 0.4515 | 0.9165 | 0.8688 | 0.097* | |
C7 | 0.6056 (6) | 1.2037 (6) | 0.5992 (4) | 0.0647 (12) | |
H7a | 0.534 | 1.2421 | 0.5258 | 0.078* | |
H7b | 0.6479 | 1.1296 | 0.5585 | 0.078* | |
C8 | 0.7787 (6) | 1.3309 (5) | 0.7008 (4) | 0.0539 (11) | |
C9 | 0.8855 (7) | 1.4075 (7) | 0.6214 (5) | 0.0702 (14) | |
C10 | 0.7274 (5) | 1.4448 (5) | 0.7832 (4) | 0.0487 (10) | |
C11 | 0.7696 (5) | 1.4510 (5) | 0.9150 (4) | 0.0541 (11) | |
H11 | 0.8286 | 1.3842 | 0.9515 | 0.065* | |
C12 | 0.6541 (7) | 1.6537 (6) | 0.9450 (5) | 0.0723 (14) | |
H12a | 0.7541 | 1.7379 | 0.9483 | 0.087* | |
H12b | 0.5913 | 1.6895 | 0.9995 | 0.087* | |
C13 | 0.5151 (7) | 1.5888 (6) | 0.7994 (5) | 0.0741 (14) | |
H13a | 0.4615 | 1.6633 | 0.7637 | 0.089* | |
H13b | 0.4131 | 1.5059 | 0.7957 | 0.089* | |
C14 | 0.6129 (6) | 1.5358 (6) | 0.7124 (4) | 0.0630 (12) | |
H14a | 0.5194 | 1.4764 | 0.6231 | 0.076* | |
H14b | 0.6945 | 1.6207 | 0.6986 | 0.076* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.1237 (7) | 0.1057 (7) | 0.1764 (9) | 0.0111 (5) | 0.0962 (6) | 0.0336 (6) |
F1 | 0.0766 (18) | 0.154 (3) | 0.0668 (17) | 0.049 (2) | 0.0368 (15) | 0.057 (2) |
F2 | 0.101 (2) | 0.143 (3) | 0.093 (2) | 0.058 (2) | 0.0676 (19) | 0.032 (2) |
F3 | 0.0562 (16) | 0.115 (3) | 0.087 (2) | 0.0144 (18) | 0.0321 (15) | 0.0345 (19) |
O1 | 0.0540 (16) | 0.078 (2) | 0.0567 (17) | 0.0314 (17) | 0.0175 (15) | 0.0126 (17) |
O2 | 0.0590 (18) | 0.089 (2) | 0.0445 (16) | 0.0315 (18) | 0.0209 (14) | 0.0103 (16) |
C1 | 0.076 (3) | 0.055 (3) | 0.092 (4) | 0.009 (3) | 0.039 (3) | 0.000 (3) |
C2 | 0.053 (3) | 0.074 (4) | 0.105 (4) | 0.008 (3) | 0.030 (3) | 0.000 (3) |
C3 | 0.053 (3) | 0.072 (3) | 0.075 (3) | 0.017 (3) | 0.017 (2) | 0.004 (3) |
C4 | 0.054 (2) | 0.061 (3) | 0.057 (3) | 0.011 (2) | 0.020 (2) | −0.008 (3) |
C5 | 0.067 (3) | 0.072 (3) | 0.076 (3) | 0.026 (3) | 0.025 (3) | 0.007 (3) |
C6 | 0.094 (4) | 0.064 (3) | 0.091 (4) | 0.027 (3) | 0.043 (3) | 0.015 (3) |
C7 | 0.056 (3) | 0.076 (3) | 0.052 (2) | 0.021 (3) | 0.017 (2) | −0.001 (2) |
C8 | 0.050 (2) | 0.070 (3) | 0.045 (2) | 0.024 (2) | 0.018 (2) | 0.015 (2) |
C9 | 0.055 (3) | 0.104 (4) | 0.059 (3) | 0.031 (3) | 0.026 (2) | 0.020 (3) |
C10 | 0.040 (2) | 0.064 (3) | 0.041 (2) | 0.014 (2) | 0.0153 (17) | 0.012 (2) |
C11 | 0.040 (2) | 0.071 (3) | 0.048 (2) | 0.019 (2) | 0.0142 (19) | 0.011 (2) |
C12 | 0.066 (3) | 0.076 (4) | 0.072 (3) | 0.027 (3) | 0.025 (3) | 0.006 (3) |
C13 | 0.069 (3) | 0.086 (4) | 0.070 (3) | 0.042 (3) | 0.021 (3) | 0.013 (3) |
C14 | 0.061 (3) | 0.073 (3) | 0.054 (2) | 0.025 (3) | 0.018 (2) | 0.016 (2) |
Geometric parameters (Å, º) top
Br1—C1 | 1.887 (6) | C4—C5 | 1.391 (7) |
F1—C9 | 1.333 (5) | C4—C7 | 1.489 (7) |
F2—C9 | 1.349 (6) | C5—C6 | 1.352 (7) |
F3—C9 | 1.324 (6) | C7—C8 | 1.530 (6) |
O1—C8 | 1.420 (5) | C8—C10 | 1.530 (6) |
O2—C11 | 1.370 (5) | C8—C9 | 1.530 (6) |
O2—C12 | 1.435 (6) | C10—C11 | 1.319 (6) |
C1—C2 | 1.363 (8) | C10—C14 | 1.497 (6) |
C1—C6 | 1.376 (8) | C12—C13 | 1.496 (7) |
C2—C3 | 1.379 (7) | C13—C14 | 1.517 (6) |
C3—C4 | 1.390 (6) | | |
| | | |
C11—O2—C12 | 115.2 (3) | C7—C8—C9 | 108.8 (4) |
C2—C1—C6 | 119.4 (5) | C10—C8—C9 | 109.9 (4) |
C2—C1—Br1 | 120.0 (4) | F3—C9—F1 | 106.8 (5) |
C6—C1—Br1 | 120.6 (5) | F3—C9—F2 | 106.9 (4) |
C1—C2—C3 | 119.6 (5) | F1—C9—F2 | 105.5 (4) |
C2—C3—C4 | 122.0 (5) | F3—C9—C8 | 112.3 (4) |
C3—C4—C5 | 116.5 (5) | F1—C9—C8 | 113.4 (4) |
C3—C4—C7 | 121.4 (5) | F2—C9—C8 | 111.4 (5) |
C5—C4—C7 | 122.1 (4) | C11—C10—C14 | 120.4 (4) |
C6—C5—C4 | 121.6 (5) | C11—C10—C8 | 118.8 (4) |
C5—C6—C1 | 121.0 (5) | C14—C10—C8 | 120.4 (3) |
C4—C7—C8 | 113.9 (4) | C10—C11—O2 | 126.2 (4) |
O1—C8—C7 | 106.6 (4) | O2—C12—C13 | 111.7 (4) |
O1—C8—C10 | 112.5 (3) | C12—C13—C14 | 109.8 (4) |
C7—C8—C10 | 112.8 (3) | C10—C14—C13 | 109.4 (4) |
O1—C8—C9 | 106.0 (3) | | |
| | | |
C6—C1—C2—C3 | −0.2 (8) | C7—C8—C9—F1 | 60.7 (5) |
Br1—C1—C2—C3 | 178.4 (4) | C10—C8—C9—F1 | −63.2 (5) |
C1—C2—C3—C4 | −0.2 (8) | O1—C8—C9—F2 | 56.1 (5) |
C2—C3—C4—C5 | 0.8 (7) | C7—C8—C9—F2 | −58.1 (5) |
C2—C3—C4—C7 | 179.8 (5) | C10—C8—C9—F2 | 178.0 (4) |
C3—C4—C5—C6 | −1.0 (7) | O1—C8—C10—C11 | −11.6 (5) |
C7—C4—C5—C6 | 180.0 (5) | C7—C8—C10—C11 | 109.0 (4) |
C4—C5—C6—C1 | 0.6 (8) | C9—C8—C10—C11 | −129.5 (4) |
C2—C1—C6—C5 | 0.1 (8) | O1—C8—C10—C14 | 174.9 (4) |
Br1—C1—C6—C5 | −178.6 (4) | C7—C8—C10—C14 | −64.5 (5) |
C3—C4—C7—C8 | 110.2 (5) | C9—C8—C10—C14 | 57.1 (5) |
C5—C4—C7—C8 | −70.8 (6) | C14—C10—C11—O2 | −7.0 (7) |
C4—C7—C8—O1 | 72.2 (4) | C8—C10—C11—O2 | 179.5 (4) |
C4—C7—C8—C10 | −51.7 (5) | C12—O2—C11—C10 | −3.5 (6) |
C4—C7—C8—C9 | −173.9 (4) | C11—O2—C12—C13 | 37.4 (5) |
O1—C8—C9—F3 | −63.8 (5) | O2—C12—C13—C14 | −60.4 (6) |
C7—C8—C9—F3 | −178.0 (4) | C11—C10—C14—C13 | −16.6 (6) |
C10—C8—C9—F3 | 58.0 (5) | C8—C10—C14—C13 | 156.7 (4) |
O1—C8—C9—F1 | 175.0 (4) | C12—C13—C14—C10 | 48.1 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···F3 | 0.82 | 2.47 | 2.785 (4) | 103.7 |
O1—H1···O2i | 0.82 | 2.12 | 2.921 (5) | 166.0 |
Symmetry code: (i) −x+2, −y+3, −z+2. |
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