Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028966/bt2389sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028966/bt2389Isup2.hkl |
CCDC reference: 654993
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.074
- wR factor = 0.199
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT430_ALERT_2_A Short Inter D...A Contact O1A .. O1A .. 2.53 Ang.
Author Response: Each of the paired O1A atoms has a C---H...O interaction besides the O1A...O1A short contact. There is no other missing interaction. |
Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.85 Ratio
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.69 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT245_ALERT_2_C U(iso) H10B Smaller than U(eq) C10 by ... 0.01 AngSq PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.10 PLAT301_ALERT_3_C Main Residue Disorder ......................... 13.00 Perc.
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 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 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature on values of bond lengths, see: Allen et al. (1987). For a related structure, see: van Alem et al. (2005)
The title compound was synthesized by a photo-induced reaction between α,α,α-trifluoroacetophenone (0.05M) and an excess amount of 1-phenyl-2-trimethyl-silylacetylene (0.2M) in a acetonitrile solution. The title compound was isolated using silica gel column chromatography. Single crystal suitable for X-ray diffraction analysis were obtained by slow evaporation of the solvents from a petroleum ether-ethyl acetate solution (V:V = 2:1).
The H atoms on C10 were located in a difference map and refined isotropically. The remaining H atoms were positional geometrically and refined as riding, with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C). The ratio of the refined occupancies for the major and minor components of the disordered linkage of C7B/C8B/O1B and C7A/C8A/O1A are 0.614 (4): 0.386 (4).
The photochemistry of α,α,α-trifluoroacetophenone is of continuing research interest (van Alem et al., 2005). In continuation of our recent work on photoinduced reactions of ketones with alkynes, the title compound, (I), was obtained by the reaction of photoexcited α,α,α-trifluoroacetophenone with trimethylsilylphenylethyne. A crystallographic analysis of (I) was carried out to elucidate its structure.
Bond lengths and angles in (I) display normal values (Allen et al., 1987). The dihedral angle between the C1—C6 and C11—C16 benzene rings is 4.66 (12)°. The torsion angle of C9—C7A—C8A—C10 and C9—C7B—C8B—C10 are 176.1 (3) and -175.5 (2)°, respectively. The linkage between the two phenyl rings is disordered over two positions.
In the crystal structure, the molecules are interconnected into columns along the b axis by intermolecular C13—H13A···O1B and C5—H5A···O1B interactions (Figure 2 and Table 1) together with intermolecular C12—H12A···O1A interactions (Table 1) and short O1A···O1A (-x, y, 1/2 - z) contacts [2.525 (8) Å] (Figure 3). In addition, the crystal structure is further stabilized by C—H···π interactions involving the C1—C6 (centroid Cg1) and C11—C16 (centroid Cg2) ring (Table 1).
For related literature on values of bond lengths, see: Allen et al. (1987). For a related structure, see: van Alem et al. (2005)
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C16H11F3O | F(000) = 1136 |
Mr = 276.25 | Dx = 1.434 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6048 reflections |
a = 29.1818 (8) Å | θ = 1.7–29.7° |
b = 5.8972 (2) Å | µ = 0.12 mm−1 |
c = 17.8356 (6) Å | T = 100 K |
β = 123.485 (3)° | Neddle, colourless |
V = 2559.92 (17) Å3 | 0.53 × 0.11 × 0.08 mm |
Z = 8 |
Bruker SMART APEX II CCD area-detector diffractometer | 3611 independent reflections |
Radiation source: fine-focus sealed tube | 2817 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 8.33 pixels mm-1 | θmax = 29.7°, θmin = 1.7° |
ω scans | h = −40→40 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −8→8 |
Tmin = 0.851, Tmax = 0.991 | l = −24→24 |
24392 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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.199 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.077P)2 + 6.0256P] where P = (Fo2 + 2Fc2)/3 |
3611 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.56 e Å−3 |
C16H11F3O | V = 2559.92 (17) Å3 |
Mr = 276.25 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 29.1818 (8) Å | µ = 0.12 mm−1 |
b = 5.8972 (2) Å | T = 100 K |
c = 17.8356 (6) Å | 0.53 × 0.11 × 0.08 mm |
β = 123.485 (3)° |
Bruker SMART APEX II CCD area-detector diffractometer | 3611 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2817 reflections with I > 2σ(I) |
Tmin = 0.851, Tmax = 0.991 | Rint = 0.035 |
24392 measured reflections |
R[F2 > 2σ(F2)] = 0.074 | 0 restraints |
wR(F2) = 0.199 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.53 e Å−3 |
3611 reflections | Δρmin = −0.56 e Å−3 |
217 parameters |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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 | 0.18069 (11) | 0.9487 (5) | 0.23530 (19) | 0.0464 (7) | |
H1A | 0.1880 | 1.0725 | 0.2726 | 0.056* | |
C2 | 0.20283 (8) | 0.9398 (4) | 0.18402 (14) | 0.0290 (4) | |
H2A | 0.2253 | 1.0566 | 0.1872 | 0.035* | |
C3 | 0.19152 (8) | 0.7565 (4) | 0.12787 (12) | 0.0265 (4) | |
H3A | 0.2062 | 0.7511 | 0.0929 | 0.032* | |
C4 | 0.15853 (8) | 0.5809 (4) | 0.12336 (13) | 0.0267 (4) | |
H4A | 0.1510 | 0.4581 | 0.0855 | 0.032* | |
C5 | 0.13670 (9) | 0.5889 (4) | 0.17546 (15) | 0.0349 (5) | |
H5A | 0.1148 | 0.4709 | 0.1731 | 0.042* | |
C6 | 0.14771 (11) | 0.7744 (5) | 0.23137 (18) | 0.0509 (8) | |
C7A | 0.1405 (2) | 0.7075 (8) | 0.3129 (3) | 0.0206 (11) | 0.386 (4) |
C8A | 0.0984 (2) | 0.8206 (8) | 0.3060 (3) | 0.0211 (11) | 0.386 (4) |
C7B | 0.12592 (13) | 0.7038 (5) | 0.3454 (2) | 0.0219 (7) | 0.614 (4) |
C8B | 0.11472 (13) | 0.8185 (5) | 0.2723 (2) | 0.0211 (7) | 0.614 (4) |
C9 | 0.17483 (9) | 0.5436 (4) | 0.39318 (14) | 0.0302 (4) | |
F1 | 0.21769 (8) | 0.5581 (4) | 0.38942 (15) | 0.0710 (6) | |
F2 | 0.15724 (7) | 0.3293 (3) | 0.37303 (13) | 0.0622 (5) | |
F3 | 0.19211 (10) | 0.5757 (4) | 0.47726 (12) | 0.0731 (6) | |
C10 | 0.06815 (8) | 0.9881 (4) | 0.23205 (13) | 0.0256 (4) | |
H10A | 0.070 (3) | 1.000 (13) | 0.174 (4) | 0.023 (16)* | 0.386 (4) |
H10B | 0.0408 (14) | 0.983 (7) | 0.252 (2) | 0.013 (8)* | 0.614 (4) |
O1A | 0.03311 (17) | 1.1142 (8) | 0.2254 (3) | 0.0326 (11) | 0.386 (4) |
O1B | 0.06237 (11) | 1.1301 (5) | 0.17911 (18) | 0.0350 (7) | 0.614 (4) |
C11 | 0.08796 (12) | 0.7462 (6) | 0.37994 (18) | 0.0550 (9) | |
C12 | 0.05262 (9) | 0.5710 (4) | 0.36590 (15) | 0.0345 (5) | |
H12A | 0.0471 | 0.4526 | 0.3273 | 0.041* | |
C13 | 0.02536 (8) | 0.5724 (4) | 0.40948 (14) | 0.0288 (4) | |
H13A | 0.0016 | 0.4546 | 0.4002 | 0.035* | |
C14 | 0.03350 (8) | 0.7491 (4) | 0.46699 (13) | 0.0296 (4) | |
H14A | 0.0153 | 0.7487 | 0.4964 | 0.036* | |
C15 | 0.06837 (9) | 0.9249 (4) | 0.48076 (14) | 0.0320 (5) | |
H15A | 0.0737 | 1.0434 | 0.5192 | 0.038* | |
C16 | 0.09546 (13) | 0.9235 (5) | 0.43669 (18) | 0.0527 (8) | |
H16A | 0.1188 | 1.0425 | 0.4453 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0506 (14) | 0.0514 (16) | 0.0622 (15) | −0.0278 (12) | 0.0469 (13) | −0.0355 (13) |
C2 | 0.0296 (9) | 0.0292 (11) | 0.0369 (10) | −0.0059 (8) | 0.0239 (9) | −0.0039 (8) |
C3 | 0.0277 (9) | 0.0340 (11) | 0.0241 (8) | 0.0014 (8) | 0.0183 (8) | 0.0018 (8) |
C4 | 0.0313 (10) | 0.0286 (10) | 0.0240 (9) | −0.0014 (8) | 0.0177 (8) | −0.0035 (7) |
C5 | 0.0420 (12) | 0.0402 (13) | 0.0352 (10) | −0.0185 (10) | 0.0293 (10) | −0.0141 (9) |
C6 | 0.0582 (15) | 0.0696 (19) | 0.0547 (14) | −0.0396 (14) | 0.0500 (13) | −0.0387 (14) |
C7A | 0.027 (2) | 0.018 (2) | 0.021 (2) | 0.0024 (19) | 0.016 (2) | 0.0051 (18) |
C8A | 0.029 (2) | 0.018 (2) | 0.020 (2) | −0.005 (2) | 0.016 (2) | −0.0026 (18) |
C7B | 0.0271 (15) | 0.0206 (15) | 0.0241 (14) | 0.0004 (12) | 0.0181 (13) | −0.0006 (12) |
C8B | 0.0265 (15) | 0.0179 (15) | 0.0251 (14) | −0.0057 (12) | 0.0181 (13) | −0.0045 (12) |
C9 | 0.0357 (11) | 0.0296 (11) | 0.0329 (10) | 0.0063 (8) | 0.0236 (9) | 0.0053 (8) |
F1 | 0.0742 (12) | 0.0783 (14) | 0.1068 (16) | 0.0048 (10) | 0.0791 (13) | 0.0040 (11) |
F2 | 0.0612 (10) | 0.0260 (8) | 0.0837 (13) | 0.0030 (7) | 0.0300 (9) | 0.0034 (8) |
F3 | 0.1158 (16) | 0.0815 (14) | 0.0529 (10) | −0.0030 (12) | 0.0660 (12) | −0.0016 (9) |
C10 | 0.0293 (9) | 0.0258 (10) | 0.0268 (9) | −0.0001 (8) | 0.0186 (8) | 0.0001 (7) |
O1A | 0.039 (2) | 0.032 (2) | 0.032 (2) | 0.0098 (17) | 0.0223 (18) | 0.0025 (17) |
O1B | 0.0350 (14) | 0.0308 (16) | 0.0430 (15) | 0.0028 (11) | 0.0239 (12) | 0.0114 (11) |
C11 | 0.0686 (17) | 0.077 (2) | 0.0508 (14) | −0.0466 (16) | 0.0525 (14) | −0.0370 (14) |
C12 | 0.0376 (11) | 0.0403 (13) | 0.0352 (10) | −0.0130 (9) | 0.0260 (9) | −0.0144 (9) |
C13 | 0.0293 (9) | 0.0304 (11) | 0.0320 (10) | −0.0040 (8) | 0.0201 (8) | 0.0028 (8) |
C14 | 0.0303 (10) | 0.0387 (12) | 0.0294 (9) | 0.0043 (9) | 0.0224 (8) | 0.0060 (8) |
C15 | 0.0421 (11) | 0.0327 (11) | 0.0278 (9) | −0.0030 (9) | 0.0235 (9) | −0.0039 (8) |
C16 | 0.0775 (19) | 0.0587 (18) | 0.0482 (14) | −0.0445 (15) | 0.0514 (15) | −0.0287 (13) |
C1—C2 | 1.382 (3) | C9—F1 | 1.292 (2) |
C1—C6 | 1.383 (3) | C9—F3 | 1.306 (3) |
C1—H1A | 0.9300 | C9—F2 | 1.337 (3) |
C2—C3 | 1.384 (3) | C10—O1B | 1.202 (3) |
C2—H2A | 0.9300 | C10—O1A | 1.216 (4) |
C3—C4 | 1.386 (3) | C10—H10A | 1.07 (6) |
C3—H3A | 0.9300 | C10—H10B | 1.04 (3) |
C4—C5 | 1.387 (3) | O1A—H10B | 0.87 (4) |
C4—H4A | 0.9300 | O1B—H10A | 0.82 (7) |
C5—C6 | 1.393 (3) | C11—C12 | 1.382 (3) |
C5—H5A | 0.9300 | C11—C16 | 1.386 (3) |
C6—C8B | 1.517 (3) | C12—C13 | 1.385 (3) |
C6—C7A | 1.629 (5) | C12—H12A | 0.9300 |
C7A—C8A | 1.343 (7) | C13—C14 | 1.387 (3) |
C7A—C9 | 1.551 (5) | C13—H13A | 0.9300 |
C8A—C10 | 1.486 (5) | C14—C15 | 1.376 (3) |
C8A—C11 | 1.571 (5) | C14—H14A | 0.9300 |
C7B—C8B | 1.340 (4) | C15—C16 | 1.389 (3) |
C7B—C9 | 1.521 (4) | C15—H15A | 0.9300 |
C7B—C11 | 1.556 (4) | C16—H16A | 0.9300 |
C8B—C10 | 1.512 (4) | ||
C2—C1—C6 | 120.3 (2) | F1—C9—C7A | 93.6 (2) |
C2—C1—H1A | 119.9 | F3—C9—C7A | 127.8 (3) |
C6—C1—H1A | 119.9 | F2—C9—C7A | 112.6 (2) |
C1—C2—C3 | 119.80 (19) | O1B—C10—O1A | 75.6 (3) |
C1—C2—H2A | 120.1 | O1B—C10—C8A | 156.5 (3) |
C3—C2—H2A | 120.1 | O1A—C10—C8A | 123.3 (3) |
C2—C3—C4 | 120.40 (17) | O1B—C10—C8B | 122.2 (2) |
C2—C3—H3A | 119.8 | O1A—C10—C8B | 159.8 (3) |
C4—C3—H3A | 119.8 | O1A—C10—H10A | 111 (4) |
C3—C4—C5 | 119.80 (18) | C8A—C10—H10A | 126 (4) |
C3—C4—H4A | 120.1 | C8B—C10—H10A | 90 (4) |
C5—C4—H4A | 120.1 | O1B—C10—H10B | 119 (2) |
C4—C5—C6 | 119.76 (19) | C8A—C10—H10B | 83 (2) |
C4—C5—H5A | 120.1 | C8B—C10—H10B | 119 (2) |
C6—C5—H5A | 120.1 | H10A—C10—H10B | 142 (4) |
C1—C6—C5 | 119.94 (19) | C10—O1A—H10B | 57 (2) |
C1—C6—C8B | 117.2 (2) | C10—O1B—H10A | 60 (4) |
C5—C6—C8B | 121.5 (2) | C12—C11—C16 | 119.9 (2) |
C1—C6—C7A | 124.3 (3) | C12—C11—C7B | 115.5 (2) |
C5—C6—C7A | 110.9 (3) | C16—C11—C7B | 123.4 (2) |
C8A—C7A—C9 | 119.2 (4) | C12—C11—C8A | 121.8 (2) |
C8A—C7A—C6 | 111.1 (4) | C16—C11—C8A | 112.1 (3) |
C9—C7A—C6 | 129.7 (3) | C11—C12—C13 | 119.7 (2) |
C7A—C8A—C10 | 118.5 (4) | C11—C12—H12A | 120.1 |
C7A—C8A—C11 | 112.0 (4) | C13—C12—H12A | 120.1 |
C10—C8A—C11 | 129.5 (4) | C12—C13—C14 | 120.14 (19) |
C8B—C7B—C9 | 120.6 (3) | C12—C13—H13A | 119.9 |
C8B—C7B—C11 | 117.4 (3) | C14—C13—H13A | 119.9 |
C9—C7B—C11 | 122.1 (2) | C15—C14—C13 | 120.37 (17) |
C7B—C8B—C10 | 117.9 (3) | C15—C14—H14A | 119.8 |
C7B—C8B—C6 | 120.2 (3) | C13—C14—H14A | 119.8 |
C10—C8B—C6 | 121.9 (3) | C14—C15—C16 | 119.4 (2) |
F1—C9—F3 | 106.2 (2) | C14—C15—H15A | 120.3 |
F1—C9—F2 | 106.72 (19) | C16—C15—H15A | 120.3 |
F3—C9—F2 | 107.1 (2) | C11—C16—C15 | 120.5 (2) |
F1—C9—C7B | 124.5 (2) | C11—C16—H16A | 119.8 |
F3—C9—C7B | 101.7 (2) | C15—C16—H16A | 119.8 |
F2—C9—C7B | 109.5 (2) | ||
C6—C1—C2—C3 | 0.6 (4) | C8A—C7A—C9—F3 | −42.2 (6) |
C1—C2—C3—C4 | −0.6 (3) | C6—C7A—C9—F3 | 136.4 (4) |
C2—C3—C4—C5 | 0.0 (3) | C8A—C7A—C9—F2 | 94.4 (4) |
C3—C4—C5—C6 | 0.6 (4) | C6—C7A—C9—F2 | −87.0 (4) |
C2—C1—C6—C5 | 0.0 (5) | C8A—C7A—C9—C7B | 2.8 (3) |
C2—C1—C6—C8B | −166.5 (3) | C6—C7A—C9—C7B | −178.6 (7) |
C2—C1—C6—C7A | 153.0 (3) | C7A—C8A—C10—O1B | −33.0 (10) |
C4—C5—C6—C1 | −0.5 (4) | C11—C8A—C10—O1B | 148.6 (6) |
C4—C5—C6—C8B | 165.4 (3) | C7A—C8A—C10—O1A | −172.6 (4) |
C4—C5—C6—C7A | −157.0 (3) | C11—C8A—C10—O1A | 8.9 (6) |
C1—C6—C7A—C8A | 90.6 (5) | C7A—C8A—C10—C8B | 1.0 (3) |
C5—C6—C7A—C8A | −114.2 (4) | C11—C8A—C10—C8B | −177.4 (6) |
C8B—C6—C7A—C8A | 1.1 (3) | C7B—C8B—C10—O1B | 164.3 (3) |
C1—C6—C7A—C9 | −88.1 (5) | C6—C8B—C10—O1B | −16.6 (4) |
C5—C6—C7A—C9 | 67.1 (5) | C7B—C8B—C10—O1A | 15.1 (10) |
C8B—C6—C7A—C9 | −177.6 (7) | C6—C8B—C10—O1A | −165.8 (8) |
C9—C7A—C8A—C10 | 176.1 (3) | C7B—C8B—C10—C8A | −0.5 (3) |
C6—C7A—C8A—C10 | −2.7 (6) | C6—C8B—C10—C8A | 178.6 (5) |
C9—C7A—C8A—C11 | −5.2 (6) | C8B—C7B—C11—C12 | 107.9 (3) |
C6—C7A—C8A—C11 | 176.0 (3) | C9—C7B—C11—C12 | −73.6 (4) |
C9—C7B—C8B—C10 | −175.5 (2) | C8B—C7B—C11—C16 | −84.8 (4) |
C11—C7B—C8B—C10 | 3.1 (4) | C9—C7B—C11—C16 | 93.7 (4) |
C9—C7B—C8B—C6 | 5.4 (4) | C8B—C7B—C11—C8A | −1.8 (3) |
C11—C7B—C8B—C6 | −176.1 (2) | C9—C7B—C11—C8A | 176.7 (5) |
C1—C6—C8B—C7B | −113.5 (4) | C7A—C8A—C11—C12 | −90.1 (5) |
C5—C6—C8B—C7B | 80.2 (4) | C10—C8A—C11—C12 | 88.5 (5) |
C7A—C6—C8B—C7B | −1.7 (3) | C7A—C8A—C11—C16 | 117.7 (4) |
C1—C6—C8B—C10 | 67.4 (4) | C10—C8A—C11—C16 | −63.8 (5) |
C5—C6—C8B—C10 | −98.9 (4) | C7A—C8A—C11—C7B | 1.1 (3) |
C7A—C6—C8B—C10 | 179.2 (5) | C10—C8A—C11—C7B | 179.6 (6) |
C8B—C7B—C9—F1 | 24.0 (4) | C16—C11—C12—C13 | −0.7 (5) |
C11—C7B—C9—F1 | −154.5 (2) | C7B—C11—C12—C13 | 167.1 (2) |
C8B—C7B—C9—F3 | 143.1 (3) | C8A—C11—C12—C13 | −150.9 (3) |
C11—C7B—C9—F3 | −35.4 (3) | C11—C12—C13—C14 | 0.0 (4) |
C8B—C7B—C9—F2 | −103.9 (3) | C12—C13—C14—C15 | 0.4 (3) |
C11—C7B—C9—F2 | 77.7 (3) | C13—C14—C15—C16 | −0.2 (3) |
C8B—C7B—C9—C7A | −2.1 (4) | C12—C11—C16—C15 | 1.0 (5) |
C11—C7B—C9—C7A | 179.4 (5) | C7B—C11—C16—C15 | −165.8 (3) |
C8A—C7A—C9—F1 | −155.8 (4) | C8A—C11—C16—C15 | 153.9 (3) |
C6—C7A—C9—F1 | 22.7 (4) | C14—C15—C16—C11 | −0.6 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···O1Bi | 0.93 | 2.56 | 3.491 (4) | 175 |
C13—H13A···O1Bii | 0.93 | 2.50 | 3.375 (4) | 158 |
C12—H12A···O1Ai | 0.93 | 2.58 | 3.506 (5) | 178 |
C2—H2A···Cg1iii | 0.93 | 2.92 | 3.668 (3) | 139 |
C4—H4A···Cg2iv | 0.93 | 2.90 | 3.662 (2) | 141 |
C15—H15A···Cg1v | 0.93 | 2.91 | 3.618 (2) | 134 |
Symmetry codes: (i) x, y−1, z; (ii) −x, y−1, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2; (iv) x, −y+1, z−1/2; (v) x, −y+2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H11F3O |
Mr | 276.25 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 100 |
a, b, c (Å) | 29.1818 (8), 5.8972 (2), 17.8356 (6) |
β (°) | 123.485 (3) |
V (Å3) | 2559.92 (17) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.53 × 0.11 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEX II CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.851, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24392, 3611, 2817 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.696 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.074, 0.199, 1.07 |
No. of reflections | 3611 |
No. of parameters | 217 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.53, −0.56 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···O1Bi | 0.93 | 2.56 | 3.491 (4) | 175 |
C13—H13A···O1Bii | 0.93 | 2.50 | 3.375 (4) | 158 |
C12—H12A···O1Ai | 0.93 | 2.58 | 3.506 (5) | 178 |
C2—H2A···Cg1iii | 0.93 | 2.92 | 3.668 (3) | 139 |
C4—H4A···Cg2iv | 0.93 | 2.90 | 3.662 (2) | 141 |
C15—H15A···Cg1v | 0.93 | 2.91 | 3.618 (2) | 134 |
Symmetry codes: (i) x, y−1, z; (ii) −x, y−1, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2; (iv) x, −y+1, z−1/2; (v) x, −y+2, z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
The photochemistry of α,α,α-trifluoroacetophenone is of continuing research interest (van Alem et al., 2005). In continuation of our recent work on photoinduced reactions of ketones with alkynes, the title compound, (I), was obtained by the reaction of photoexcited α,α,α-trifluoroacetophenone with trimethylsilylphenylethyne. A crystallographic analysis of (I) was carried out to elucidate its structure.
Bond lengths and angles in (I) display normal values (Allen et al., 1987). The dihedral angle between the C1—C6 and C11—C16 benzene rings is 4.66 (12)°. The torsion angle of C9—C7A—C8A—C10 and C9—C7B—C8B—C10 are 176.1 (3) and -175.5 (2)°, respectively. The linkage between the two phenyl rings is disordered over two positions.
In the crystal structure, the molecules are interconnected into columns along the b axis by intermolecular C13—H13A···O1B and C5—H5A···O1B interactions (Figure 2 and Table 1) together with intermolecular C12—H12A···O1A interactions (Table 1) and short O1A···O1A (-x, y, 1/2 - z) contacts [2.525 (8) Å] (Figure 3). In addition, the crystal structure is further stabilized by C—H···π interactions involving the C1—C6 (centroid Cg1) and C11—C16 (centroid Cg2) ring (Table 1).