4-Fluoro­phenyl 4-{1,1,1,3,3,3-hexa­fluoro-2-[4-(4-fluoro­benzo­yl)phen­yl]-2-prop­yl}phenyl ketone

In the title compound, C₂₉H₁₆F₈O₂, in spite of the symmetric substitution at the hexa­fluoro­propane group, an unsymmetrical conformation is obtained for the fluoro­benzoyl substituents. One substituent is oriented syn and the other anti to the central group.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.056
• wR factor = 0.161
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT432_ALERT_2_C Short Inter X...Y Contact  F2     ..  C14     ..       2.94 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1997); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

4-Fluorophenyl 4-{1,1,1,3,3,3-hexafluoro-2-[4-(4-fluorobenzoyl)phenyl]-2-propyl}phenyl ketone

Crystal data

C29H16F8O2	F(000) = 1112
Mr = 548.42	Dx = 1.507 Mg m^−3
Monoclinic, P21/n	Melting point: 616 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 9.940 (2) Å	Cell parameters from 78 reflections
b = 11.202 (5) Å	θ = 4.1–14.7°
c = 21.710 (9) Å	µ = 0.14 mm^−1
β = 90.68 (4)°	T = 298 K
V = 2417.2 (16) Å^3	Prism, colourless
Z = 4	0.60 × 0.16 × 0.04 mm

Data collection

Bruker P4 diffractometer	Rint = 0.023
Radiation source: fine-focus sealed tube	θmax = 25.4°, θmin = 2.1°
Graphite monochromator	h = −1→11
ω scans	k = −1→13
5765 measured reflections	l = −26→26
4396 independent reflections	3 standard reflections every 97 reflections
2319 reflections with I > 2σ(I)	intensity decay: <1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.161	w = 1/[σ^2(Fo^2) + (0.0533P)^2 + 1.9495P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4396 reflections	Δρmax = 0.25 e Å^−3
353 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXTL-Plus, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0072 (10)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.7990 (2)	0.7538 (2)	0.00129 (10)	0.0803 (7)
F2	0.8197 (2)	0.82626 (19)	0.09195 (10)	0.0710 (6)
F3	0.7073 (2)	0.9208 (2)	0.02305 (11)	0.0811 (7)
F4	0.3989 (2)	0.6794 (2)	0.02094 (10)	0.0719 (6)
F5	0.5807 (2)	0.6205 (2)	−0.02083 (10)	0.0774 (7)
F6	0.5136 (2)	0.8000 (2)	−0.03372 (9)	0.0785 (7)
F7	1.0615 (3)	−0.0324 (2)	0.09290 (16)	0.1132 (10)
F8	0.3581 (3)	1.0514 (3)	0.47961 (12)	0.1179 (11)
O1	0.6289 (3)	0.2649 (3)	0.23461 (13)	0.0861 (9)
O2	0.3038 (4)	1.1917 (3)	0.20095 (15)	0.1014 (11)
C1	0.7323 (4)	0.8114 (3)	0.04559 (17)	0.0592 (10)
C2	0.6038 (3)	0.7480 (3)	0.06619 (15)	0.0490 (8)
C3	0.5235 (4)	0.7118 (4)	0.00835 (16)	0.0594 (10)
C4	0.6338 (3)	0.6314 (3)	0.10121 (14)	0.0485 (8)
C5	0.7597 (3)	0.5785 (3)	0.10298 (16)	0.0556 (9)
H5A	0.8323	0.6169	0.0850	0.067*
C6	0.7783 (4)	0.4688 (3)	0.13128 (16)	0.0578 (10)
H6A	0.8636	0.4347	0.1322	0.069*
C7	0.6724 (3)	0.4092 (3)	0.15815 (15)	0.0501 (9)
C8	0.5472 (4)	0.4630 (3)	0.15765 (15)	0.0543 (9)
H8A	0.4749	0.4248	0.1760	0.065*
C9	0.5284 (3)	0.5732 (3)	0.13017 (15)	0.0514 (9)
H9A	0.4440	0.6090	0.1311	0.062*
C10	0.6918 (4)	0.2906 (3)	0.18851 (17)	0.0588 (10)
C11	0.7898 (4)	0.2057 (3)	0.16189 (16)	0.0585 (10)
C12	0.8238 (4)	0.2071 (3)	0.10018 (18)	0.0646 (10)
H12A	0.7843	0.2631	0.0740	0.078*
C13	0.9152 (4)	0.1269 (4)	0.0768 (2)	0.0767 (12)
H13A	0.9373	0.1277	0.0353	0.092*
C14	0.9720 (4)	0.0468 (4)	0.1162 (3)	0.0789 (13)
C15	0.9400 (5)	0.0399 (4)	0.1768 (2)	0.0874 (14)
H15A	0.9798	−0.0172	0.2023	0.105*
C16	0.8474 (5)	0.1190 (4)	0.1997 (2)	0.0777 (12)
H16A	0.8231	0.1144	0.2408	0.093*
C17	0.5293 (3)	0.8381 (3)	0.10712 (15)	0.0518 (9)
C18	0.4264 (4)	0.9117 (3)	0.08632 (17)	0.0618 (10)
H18A	0.3942	0.9038	0.0461	0.074*
C19	0.3710 (4)	0.9962 (3)	0.12446 (18)	0.0655 (11)
H19A	0.3032	1.0458	0.1094	0.079*
C20	0.4146 (4)	1.0087 (3)	0.18472 (17)	0.0590 (10)
C21	0.5185 (4)	0.9356 (3)	0.20530 (17)	0.0655 (11)
H21A	0.5500	0.9433	0.2456	0.079*
C22	0.5757 (4)	0.8520 (3)	0.16736 (16)	0.0604 (10)
H22A	0.6457	0.8045	0.1821	0.072*
C23	0.3526 (4)	1.1021 (4)	0.22442 (19)	0.0674 (11)
C24	0.3530 (4)	1.0861 (3)	0.29236 (18)	0.0606 (10)
C25	0.3353 (4)	0.9752 (4)	0.3188 (2)	0.0667 (11)
H25A	0.3231	0.9083	0.2940	0.080*
C26	0.3356 (4)	0.9637 (4)	0.3826 (2)	0.0767 (12)
H26A	0.3233	0.8895	0.4009	0.092*
C27	0.3545 (4)	1.0632 (5)	0.4175 (2)	0.0780 (13)
C28	0.3705 (4)	1.1732 (4)	0.3928 (2)	0.0791 (13)
H28A	0.3829	1.2395	0.4180	0.095*
C29	0.3683 (4)	1.1854 (4)	0.3296 (2)	0.0714 (11)
H29A	0.3771	1.2606	0.3120	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0806 (15)	0.0812 (16)	0.0798 (15)	−0.0119 (13)	0.0305 (13)	−0.0027 (13)
F2	0.0599 (13)	0.0663 (14)	0.0865 (15)	−0.0122 (11)	−0.0056 (12)	−0.0031 (12)
F3	0.0867 (16)	0.0622 (15)	0.0943 (17)	−0.0123 (13)	0.0031 (13)	0.0227 (13)
F4	0.0630 (14)	0.0862 (17)	0.0662 (13)	−0.0133 (12)	−0.0098 (11)	0.0045 (12)
F5	0.0941 (17)	0.0789 (16)	0.0591 (13)	−0.0043 (13)	−0.0025 (12)	−0.0170 (12)
F6	0.0963 (17)	0.0828 (16)	0.0560 (12)	−0.0088 (13)	−0.0099 (12)	0.0141 (12)
F7	0.0782 (17)	0.0795 (19)	0.182 (3)	0.0148 (15)	0.0153 (18)	−0.0192 (19)
F8	0.112 (2)	0.168 (3)	0.0741 (17)	0.024 (2)	0.0156 (15)	0.0095 (19)
O1	0.103 (2)	0.080 (2)	0.0755 (19)	0.0096 (18)	0.0259 (17)	0.0184 (16)
O2	0.143 (3)	0.072 (2)	0.089 (2)	0.046 (2)	0.007 (2)	0.0073 (18)
C1	0.061 (2)	0.056 (2)	0.060 (2)	−0.007 (2)	0.004 (2)	0.000 (2)
C2	0.050 (2)	0.049 (2)	0.0487 (19)	−0.0009 (17)	0.0007 (16)	0.0017 (16)
C3	0.067 (3)	0.061 (2)	0.051 (2)	−0.002 (2)	−0.0028 (19)	−0.001 (2)
C4	0.050 (2)	0.052 (2)	0.0432 (18)	−0.0049 (17)	0.0012 (15)	−0.0053 (16)
C5	0.047 (2)	0.056 (2)	0.064 (2)	−0.0030 (18)	0.0058 (17)	0.0027 (19)
C6	0.049 (2)	0.056 (2)	0.068 (2)	0.0024 (18)	−0.0011 (18)	0.002 (2)
C7	0.052 (2)	0.051 (2)	0.0474 (19)	−0.0020 (18)	−0.0006 (16)	−0.0017 (17)
C8	0.052 (2)	0.059 (2)	0.052 (2)	−0.0030 (19)	0.0043 (17)	0.0020 (18)
C9	0.0435 (19)	0.056 (2)	0.055 (2)	0.0024 (17)	−0.0001 (16)	−0.0022 (18)
C10	0.064 (2)	0.056 (2)	0.056 (2)	−0.002 (2)	−0.0025 (19)	0.0014 (19)
C11	0.065 (2)	0.054 (2)	0.056 (2)	−0.0023 (19)	−0.0055 (19)	0.0038 (18)
C12	0.073 (3)	0.052 (2)	0.069 (3)	0.005 (2)	0.000 (2)	0.004 (2)
C13	0.078 (3)	0.067 (3)	0.085 (3)	0.002 (2)	0.013 (2)	−0.004 (3)
C14	0.062 (3)	0.059 (3)	0.116 (4)	0.005 (2)	0.005 (3)	−0.017 (3)
C15	0.096 (3)	0.066 (3)	0.100 (4)	0.019 (3)	−0.021 (3)	0.002 (3)
C16	0.100 (3)	0.062 (3)	0.071 (3)	0.005 (3)	−0.010 (2)	0.006 (2)
C17	0.054 (2)	0.051 (2)	0.051 (2)	0.0002 (18)	−0.0022 (16)	0.0025 (17)
C18	0.069 (2)	0.063 (2)	0.053 (2)	0.007 (2)	−0.0108 (19)	0.004 (2)
C19	0.065 (2)	0.059 (2)	0.072 (3)	0.015 (2)	−0.008 (2)	0.005 (2)
C20	0.064 (2)	0.055 (2)	0.058 (2)	0.0064 (19)	0.0016 (19)	0.0028 (18)
C21	0.075 (3)	0.069 (3)	0.052 (2)	0.015 (2)	−0.0070 (19)	−0.007 (2)
C22	0.064 (2)	0.059 (2)	0.058 (2)	0.017 (2)	−0.0077 (19)	−0.0041 (19)
C23	0.074 (3)	0.053 (2)	0.075 (3)	0.014 (2)	0.006 (2)	0.002 (2)
C24	0.056 (2)	0.054 (2)	0.071 (3)	0.0056 (19)	0.0160 (19)	−0.005 (2)
C25	0.062 (2)	0.059 (3)	0.080 (3)	−0.001 (2)	0.011 (2)	−0.002 (2)
C26	0.065 (3)	0.078 (3)	0.088 (3)	0.002 (2)	0.023 (2)	0.021 (3)
C27	0.057 (3)	0.112 (4)	0.066 (3)	0.009 (3)	0.014 (2)	0.005 (3)
C28	0.075 (3)	0.083 (3)	0.079 (3)	−0.005 (3)	0.020 (2)	−0.015 (3)
C29	0.073 (3)	0.062 (3)	0.080 (3)	−0.005 (2)	0.023 (2)	−0.004 (2)

Geometric parameters (Å, º)

F1—C1	1.340 (4)	C12—H12A	0.9300
F2—C1	1.332 (4)	C13—C14	1.359 (6)
F3—C1	1.341 (4)	C13—H13A	0.9300
F4—C3	1.323 (4)	C14—C15	1.359 (6)
F5—C3	1.334 (4)	C15—C16	1.374 (6)
F6—C3	1.348 (4)	C15—H15A	0.9300
F7—C14	1.359 (5)	C16—H16A	0.9300
F8—C27	1.355 (5)	C17—C18	1.385 (5)
O1—C10	1.221 (4)	C17—C22	1.390 (5)
O2—C23	1.223 (4)	C18—C19	1.377 (5)
C1—C2	1.533 (5)	C18—H18A	0.9300
C2—C3	1.534 (5)	C19—C20	1.380 (5)
C2—C4	1.539 (5)	C19—H19A	0.9300
C2—C17	1.541 (5)	C20—C21	1.388 (5)
C4—C5	1.385 (5)	C20—C23	1.494 (5)
C4—C9	1.390 (5)	C21—C22	1.374 (5)
C5—C6	1.385 (5)	C21—H21A	0.9300
C5—H5A	0.9300	C22—H22A	0.9300
C6—C7	1.382 (5)	C23—C24	1.486 (5)
C6—H6A	0.9300	C24—C25	1.381 (5)
C7—C8	1.383 (5)	C24—C29	1.382 (5)
C7—C10	1.494 (5)	C25—C26	1.389 (6)
C8—C9	1.383 (5)	C25—H25A	0.9300
C8—H8A	0.9300	C26—C27	1.360 (6)
C9—H9A	0.9300	C26—H26A	0.9300
C10—C11	1.484 (5)	C27—C28	1.354 (6)
C11—C12	1.386 (5)	C28—C29	1.378 (6)
C11—C16	1.391 (5)	C28—H28A	0.9300
C12—C13	1.378 (5)	C29—H29A	0.9300
F2—C1—F1	106.2 (3)	C14—C13—H13A	121.0
F2—C1—F3	106.2 (3)	C12—C13—H13A	121.0
F1—C1—F3	105.6 (3)	F7—C14—C13	117.8 (5)
F2—C1—C2	112.1 (3)	F7—C14—C15	119.1 (5)
F1—C1—C2	114.0 (3)	C13—C14—C15	123.1 (4)
F3—C1—C2	112.2 (3)	C14—C15—C16	118.6 (4)
C1—C2—C3	108.1 (3)	C14—C15—H15A	120.7
C1—C2—C4	112.4 (3)	C16—C15—H15A	120.7
C3—C2—C4	106.0 (3)	C15—C16—C11	120.7 (4)
C1—C2—C17	105.8 (3)	C15—C16—H16A	119.7
C3—C2—C17	113.4 (3)	C11—C16—H16A	119.7
C4—C2—C17	111.3 (3)	C18—C17—C22	118.4 (3)
F4—C3—F5	107.1 (3)	C18—C17—C2	124.1 (3)
F4—C3—F6	106.2 (3)	C22—C17—C2	117.4 (3)
F5—C3—F6	105.6 (3)	C19—C18—C17	120.8 (3)
F4—C3—C2	112.5 (3)	C19—C18—H18A	119.6
O1—C10—C11	120.9 (3)	C17—C18—H18A	119.6
O1—C10—C7	120.4 (3)	C18—C19—C20	121.1 (3)
O2—C23—C24	120.6 (4)	C18—C19—H19A	119.5
O2—C23—C20	119.9 (4)	C20—C19—H19A	119.5
F5—C3—C2	111.8 (3)	C19—C20—C21	118.0 (3)
F6—C3—C2	113.2 (3)	C19—C20—C23	119.4 (3)
C5—C4—C9	118.2 (3)	C21—C20—C23	122.6 (3)
C5—C4—C2	123.1 (3)	C22—C21—C20	121.4 (3)
C9—C4—C2	118.6 (3)	C22—C21—H21A	119.3
C4—C5—C6	120.5 (3)	C20—C21—H21A	119.3
C4—C5—H5A	119.7	C21—C22—C17	120.3 (3)
C6—C5—H5A	119.7	C21—C22—H22A	119.8
C7—C6—C5	121.2 (3)	C17—C22—H22A	119.8
C7—C6—H6A	119.4	C24—C23—C20	119.5 (3)
C5—C6—H6A	119.4	C25—C24—C29	119.6 (4)
C6—C7—C8	118.4 (3)	C25—C24—C23	121.5 (4)
C6—C7—C10	121.4 (3)	C29—C24—C23	118.9 (4)
C8—C7—C10	120.2 (3)	C24—C25—C26	120.0 (4)
C9—C8—C7	120.6 (3)	C24—C25—H25A	120.0
C9—C8—H8A	119.7	C26—C25—H25A	120.0
C7—C8—H8A	119.7	C27—C26—C25	118.5 (4)
C8—C9—C4	121.0 (3)	C27—C26—H26A	120.7
C8—C9—H9A	119.5	C25—C26—H26A	120.7
C4—C9—H9A	119.5	C28—C27—F8	118.8 (5)
C11—C10—C7	118.7 (3)	C28—C27—C26	122.8 (4)
C12—C11—C16	118.3 (4)	F8—C27—C26	118.5 (5)
C12—C11—C10	122.6 (3)	C27—C28—C29	118.9 (4)
C16—C11—C10	119.1 (4)	C27—C28—H28A	120.5
C13—C12—C11	121.2 (4)	C29—C28—H28A	120.5
C13—C12—H12A	119.4	C28—C29—C24	120.2 (4)
C11—C12—H12A	119.4	C28—C29—H29A	119.9
C14—C13—C12	118.0 (4)	C24—C29—H29A	119.9
C14—F7—F8—C27	−62.2 (10)	F8—F7—C14—C13	114.9 (11)
F2—C1—C2—C3	−168.3 (3)	F8—F7—C14—C15	−67.3 (9)
F1—C1—C2—C3	−47.7 (4)	C12—C13—C14—F7	179.7 (4)
F3—C1—C2—C3	72.3 (4)	C12—C13—C14—C15	2.0 (7)
F2—C1—C2—C4	−51.7 (4)	F7—C14—C15—C16	−178.8 (4)
F1—C1—C2—C4	68.9 (4)	C13—C14—C15—C16	−1.2 (7)
F3—C1—C2—C4	−171.1 (3)	C14—C15—C16—C11	−1.3 (7)
F2—C1—C2—C17	69.9 (4)	C12—C11—C16—C15	2.7 (6)
F1—C1—C2—C17	−169.4 (3)	C10—C11—C16—C15	−179.1 (4)
F3—C1—C2—C17	−49.4 (4)	C1—C2—C17—C18	96.6 (4)
C1—C2—C3—F4	−166.6 (3)	C3—C2—C17—C18	−21.7 (5)
C4—C2—C3—F4	72.7 (4)	C4—C2—C17—C18	−141.1 (3)
C17—C2—C3—F4	−49.6 (4)	C1—C2—C17—C22	−78.5 (4)
C1—C2—C3—F5	72.9 (4)	C3—C2—C17—C22	163.2 (3)
C4—C2—C3—F5	−47.8 (4)	C4—C2—C17—C22	43.8 (4)
C17—C2—C3—F5	−170.1 (3)	C22—C17—C18—C19	−0.2 (6)
C1—C2—C3—F6	−46.2 (4)	C2—C17—C18—C19	−175.2 (3)
C4—C2—C3—F6	−166.9 (3)	C17—C18—C19—C20	−1.2 (6)
C17—C2—C3—F6	70.8 (4)	C18—C19—C20—C21	1.7 (6)
C1—C2—C4—C5	−12.0 (4)	C18—C19—C20—C23	179.5 (4)
C3—C2—C4—C5	105.9 (4)	C19—C20—C21—C22	−0.8 (6)
C17—C2—C4—C5	−130.5 (3)	C23—C20—C21—C22	−178.6 (4)
C1—C2—C4—C9	171.0 (3)	C20—C21—C22—C17	−0.6 (6)
C3—C2—C4—C9	−71.1 (4)	C18—C17—C22—C21	1.1 (6)
C17—C2—C4—C9	52.5 (4)	C2—C17—C22—C21	176.5 (3)
C9—C4—C5—C6	2.0 (5)	C19—C20—C23—O2	−26.6 (6)
C2—C4—C5—C6	−175.0 (3)	C21—C20—C23—O2	151.2 (4)
C4—C5—C6—C7	0.3 (5)	C19—C20—C23—C24	154.4 (4)
C5—C6—C7—C8	−1.7 (5)	C21—C20—C23—C24	−27.9 (6)
C5—C6—C7—C10	179.8 (3)	O2—C23—C24—C25	144.0 (4)
C6—C7—C8—C9	0.8 (5)	C20—C23—C24—C25	−37.0 (6)
C10—C7—C8—C9	179.4 (3)	O2—C23—C24—C29	−34.5 (6)
C7—C8—C9—C4	1.5 (5)	C20—C23—C24—C29	144.5 (4)
C5—C4—C9—C8	−2.8 (5)	C29—C24—C25—C26	−1.3 (6)
C2—C4—C9—C8	174.3 (3)	C23—C24—C25—C26	−179.7 (4)
C6—C7—C10—O1	144.2 (4)	C24—C25—C26—C27	−0.4 (6)
C8—C7—C10—O1	−34.4 (5)	F7—F8—C27—C28	−142.3 (4)
C6—C7—C10—C11	−35.2 (5)	F7—F8—C27—C26	37.3 (3)
C8—C7—C10—C11	146.2 (3)	C25—C26—C27—C28	1.2 (7)
O1—C10—C11—C12	154.3 (4)	C25—C26—C27—F8	−178.4 (3)
C7—C10—C11—C12	−26.2 (5)	F8—C27—C28—C29	179.4 (4)
O1—C10—C11—C16	−23.8 (6)	C26—C27—C28—C29	−0.2 (7)
C7—C10—C11—C16	155.6 (3)	C27—C28—C29—C24	−1.5 (6)
C16—C11—C12—C13	−1.8 (6)	C25—C24—C29—C28	2.2 (6)
C10—C11—C12—C13	−180.0 (4)	C23—C24—C29—C28	−179.3 (4)
C11—C12—C13—C14	−0.5 (6)