(E)-4,4,4-Trifluoro-2,3-diphenyl­but-2-enal

Fun, H.-K.; Ng, S.-L.; Li, Z.; Xu, J.-H.

doi:10.1107/S1600536807028966

(E)-4,4,4-Trifluoro-2,3-diphenylbut-2-enal

In the title compound, C₁₆H₁₁F₃O, the dihedral angle between the two benzene rings is 4.66 (12)°. In the crystal structure, the molecules are interlinked into columns along the b axis by intermolecular C—H

O interactions and short O

O contacts [2.525 (8) Å]. The crystal structure is further stabilized by weak intermolecular C—H

π interactions. The linkage between the two phenyl rings is disordered over two positions in approximately a 0.6:0.4 ratio.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028966/bt2389sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028966/bt2389Isup2.hkl Contains datablock I

CCDC reference: 654993

checkCIF report

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

Comment top

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).

Related literature top

For related literature on values of bond lengths, see: Allen et al. (1987). For a related structure, see: van Alem et al. (2005)

Experimental top

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).

Structure description top

For related literature on values of bond lengths, see: Allen et al. (1987). For a related structure, see: van Alem et al. (2005)

Computing details top

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).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Both disorder components are shown.
	Fig. 2. Packing of the major component of the crystal structure of (I), viewed down the b axis. Dashed lines indicate intermolecular C—H···O interactions.
	Fig. 3. Packing of the minor component of the crystal structure of (I), viewed down the b axis. Dashed lines indicate intermolecular C—H···O interactions and short O···O contact.

(E)-4,4,4-Trifluoro-2,3-diphenylbut-2-enal top

Crystal data top

C₁₆H₁₁F₃O	F(000) = 1136
M_r = 276.25	D_x = 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

Data collection top

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	R_int = 0.035
Detector resolution: 8.33 pixels mm^-1	θ_max = 29.7°, θ_min = 1.7°
ω scans	h = −40→40
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
T_min = 0.851, T_max = 0.991	l = −24→24
24392 measured reflections

Refinement top

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(F_o²) + (0.077P)² + 6.0256P] where P = (F_o² + 2F_c²)/3
3611 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₆H₁₁F₃O	V = 2559.92 (17) Å³
M_r = 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)°

Data collection top

Bruker SMART APEX II CCD area-detector diffractometer	3611 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2817 reflections with I > 2σ(I)
T_min = 0.851, T_max = 0.991	R_int = 0.035
24392 measured reflections

Refinement top

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	Δρ_max = 0.53 e Å⁻³
3611 reflections	Δρ_min = −0.56 e Å⁻³
217 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg2^iv	0.93	2.90	3.662 (2)	141
C15—H15A···Cg1^v	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
M_r	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)
T_min, T_max	0.851, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	24392, 3611, 2817
R_int	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
Δρ_max, Δρ_min (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).