organic compounds
In the structure of the title molecule, C17H8Cl2F6O2, the dihedral angle between the least-squares planes of the benzene rings is 66.31 (15)°. The CF3 groups adopt an eclipsed conformation.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028236/sa2010sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028236/sa2010Isup2.hkl |
CCDC reference: 618318
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.064
- wR factor = 0.196
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O2 - C17 .. 5.52 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 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
Computing details top
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.
4,4'-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)bis(benzoyl chloride) top
Crystal data top
C17H8Cl2F6O2 | F(000) = 1712 |
Mr = 429.13 | Dx = 1.650 Mg m−3 |
Monoclinic, C2/c | Melting point: 416 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 19.338 (9) Å | Cell parameters from 56 reflections |
b = 12.299 (4) Å | θ = 4.7–12.4° |
c = 14.677 (4) Å | µ = 0.45 mm−1 |
β = 98.12 (3)° | T = 298 K |
V = 3456 (2) Å3 | Needle, colourless |
Z = 8 | 0.60 × 0.20 × 0.18 mm |
Data collection top
Bruker P4 diffractometer | Rint = 0.031 |
Radiation source: fine-focus sealed tube | θmax = 25.4°, θmin = 2.1° |
Graphite monochromator | h = −23→1 |
ω scans | k = −1→14 |
3727 measured reflections | l = −17→17 |
3122 independent reflections | 3 standard reflections every 97 reflections |
1830 reflections with I > 2σ(I) | intensity decay: 6.4% |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.196 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0714P)2 + 9.4954P] where P = (Fo2 + 2Fc2)/3 |
3122 reflections | (Δ/σ)max = 0.001 |
244 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.7100 (3) | 0.3099 (5) | 0.3006 (4) | 0.0761 (15) | |
C2 | 0.7030 (2) | 0.3310 (3) | 0.1969 (3) | 0.0535 (10) | |
C3 | 0.7038 (2) | 0.2199 (4) | 0.1463 (4) | 0.0680 (13) | |
C4 | 0.6335 (2) | 0.3917 (3) | 0.1701 (3) | 0.0504 (10) | |
C5 | 0.5709 (2) | 0.3407 (4) | 0.1397 (3) | 0.0618 (12) | |
H5A | 0.5698 | 0.2655 | 0.1333 | 0.074* | |
C6 | 0.5099 (2) | 0.3990 (4) | 0.1187 (3) | 0.0629 (12) | |
H6A | 0.4683 | 0.3632 | 0.0982 | 0.075* | |
C7 | 0.5105 (2) | 0.5109 (4) | 0.1281 (3) | 0.0559 (11) | |
C8 | 0.5721 (2) | 0.5627 (4) | 0.1603 (3) | 0.0584 (11) | |
H8A | 0.5729 | 0.6378 | 0.1674 | 0.070* | |
C9 | 0.6327 (2) | 0.5038 (4) | 0.1820 (3) | 0.0577 (11) | |
H9A | 0.6738 | 0.5397 | 0.2050 | 0.069* | |
C10 | 0.4426 (2) | 0.5677 (5) | 0.1025 (3) | 0.0677 (13) | |
C11 | 0.7653 (2) | 0.3956 (3) | 0.1689 (3) | 0.0509 (10) | |
C12 | 0.8292 (2) | 0.4053 (4) | 0.2261 (3) | 0.0652 (12) | |
H12A | 0.8353 | 0.3736 | 0.2842 | 0.078* | |
C13 | 0.8832 (2) | 0.4626 (4) | 0.1956 (4) | 0.0658 (13) | |
H13A | 0.9258 | 0.4682 | 0.2334 | 0.079* | |
C14 | 0.8749 (2) | 0.5110 (4) | 0.1106 (4) | 0.0632 (12) | |
C15 | 0.8115 (2) | 0.5006 (4) | 0.0545 (3) | 0.0632 (12) | |
H15A | 0.8053 | 0.5326 | −0.0035 | 0.076* | |
C16 | 0.7578 (2) | 0.4436 (4) | 0.0835 (3) | 0.0590 (11) | |
H16A | 0.7155 | 0.4373 | 0.0448 | 0.071* | |
C17 | 0.9346 (3) | 0.5727 (5) | 0.0860 (5) | 0.0878 (17) | |
O1 | 0.38988 (18) | 0.5265 (4) | 0.0704 (3) | 0.0918 (12) | |
O2 | 0.9919 (2) | 0.5810 (4) | 0.1262 (4) | 0.131 (2) | |
F1 | 0.76061 (17) | 0.2385 (3) | 0.3309 (2) | 0.0973 (11) | |
F2 | 0.65087 (17) | 0.2690 (3) | 0.3244 (2) | 0.0967 (10) | |
F3 | 0.72308 (16) | 0.4012 (3) | 0.3479 (2) | 0.0861 (9) | |
F4 | 0.76753 (15) | 0.1775 (2) | 0.1554 (2) | 0.0887 (10) | |
F5 | 0.66239 (16) | 0.1456 (2) | 0.1762 (3) | 0.0958 (11) | |
F6 | 0.68282 (15) | 0.2318 (2) | 0.0564 (2) | 0.0791 (8) | |
Cl1 | 0.44406 (8) | 0.70990 (13) | 0.12276 (12) | 0.0931 (5) | |
Cl2 | 0.92003 (11) | 0.6431 (2) | −0.01868 (14) | 0.1394 (9) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.063 (3) | 0.085 (4) | 0.081 (4) | 0.011 (3) | 0.012 (3) | 0.024 (3) |
C2 | 0.046 (2) | 0.052 (2) | 0.063 (3) | 0.0036 (19) | 0.0092 (19) | 0.002 (2) |
C3 | 0.057 (3) | 0.055 (3) | 0.095 (4) | 0.002 (2) | 0.019 (3) | −0.004 (3) |
C4 | 0.043 (2) | 0.051 (2) | 0.058 (3) | −0.0032 (18) | 0.0111 (18) | −0.002 (2) |
C5 | 0.051 (2) | 0.052 (3) | 0.084 (3) | −0.009 (2) | 0.015 (2) | 0.000 (2) |
C6 | 0.038 (2) | 0.076 (3) | 0.075 (3) | −0.007 (2) | 0.010 (2) | −0.003 (3) |
C7 | 0.041 (2) | 0.072 (3) | 0.056 (3) | 0.003 (2) | 0.0145 (18) | 0.002 (2) |
C8 | 0.050 (2) | 0.054 (3) | 0.074 (3) | 0.004 (2) | 0.016 (2) | −0.006 (2) |
C9 | 0.044 (2) | 0.059 (3) | 0.070 (3) | −0.001 (2) | 0.009 (2) | −0.008 (2) |
C10 | 0.050 (3) | 0.092 (4) | 0.064 (3) | 0.013 (3) | 0.020 (2) | 0.014 (3) |
C11 | 0.041 (2) | 0.051 (2) | 0.062 (3) | 0.0028 (18) | 0.0109 (18) | −0.001 (2) |
C12 | 0.047 (2) | 0.073 (3) | 0.073 (3) | 0.011 (2) | 0.000 (2) | −0.002 (3) |
C13 | 0.040 (2) | 0.075 (3) | 0.081 (4) | −0.001 (2) | 0.001 (2) | −0.009 (3) |
C14 | 0.043 (2) | 0.062 (3) | 0.087 (4) | −0.008 (2) | 0.015 (2) | −0.011 (3) |
C15 | 0.053 (3) | 0.069 (3) | 0.067 (3) | −0.005 (2) | 0.007 (2) | −0.002 (2) |
C16 | 0.040 (2) | 0.062 (3) | 0.074 (3) | −0.007 (2) | 0.002 (2) | −0.004 (2) |
C17 | 0.064 (3) | 0.090 (4) | 0.114 (5) | −0.015 (3) | 0.026 (3) | −0.011 (4) |
O1 | 0.0452 (19) | 0.122 (3) | 0.106 (3) | 0.004 (2) | 0.0026 (18) | 0.015 (3) |
O2 | 0.053 (2) | 0.153 (4) | 0.178 (5) | −0.043 (3) | −0.018 (3) | 0.021 (4) |
F1 | 0.086 (2) | 0.107 (2) | 0.098 (2) | 0.0335 (19) | 0.0096 (17) | 0.036 (2) |
F2 | 0.083 (2) | 0.117 (3) | 0.095 (2) | 0.0035 (19) | 0.0323 (17) | 0.035 (2) |
F3 | 0.083 (2) | 0.108 (2) | 0.0663 (18) | 0.0131 (18) | 0.0093 (15) | −0.0041 (18) |
F4 | 0.0696 (18) | 0.0653 (17) | 0.132 (3) | 0.0194 (15) | 0.0169 (17) | −0.0050 (18) |
F5 | 0.089 (2) | 0.0537 (16) | 0.150 (3) | −0.0063 (16) | 0.033 (2) | 0.0090 (18) |
F6 | 0.0741 (18) | 0.0701 (18) | 0.093 (2) | −0.0044 (14) | 0.0123 (16) | −0.0206 (16) |
Cl1 | 0.0748 (9) | 0.0898 (10) | 0.1158 (12) | 0.0315 (7) | 0.0170 (8) | 0.0113 (9) |
Cl2 | 0.1214 (15) | 0.182 (2) | 0.1163 (15) | −0.0742 (15) | 0.0227 (11) | 0.0224 (14) |
Geometric parameters (Å, º) top
C10—O1 | 1.176 (6) | C7—C8 | 1.374 (6) |
C10—Cl1 | 1.774 (6) | C7—C10 | 1.488 (6) |
C17—O2 | 1.184 (7) | C8—C9 | 1.375 (6) |
C17—Cl2 | 1.751 (7) | C11—C16 | 1.374 (6) |
C1—F3 | 1.326 (7) | C11—C12 | 1.397 (6) |
C1—F2 | 1.339 (6) | C12—C13 | 1.386 (7) |
C1—F1 | 1.343 (6) | C13—C14 | 1.370 (7) |
C1—C2 | 1.531 (7) | C14—C15 | 1.383 (6) |
C2—C4 | 1.539 (6) | C14—C17 | 1.469 (7) |
C2—C11 | 1.547 (6) | C15—C16 | 1.371 (6) |
C2—C3 | 1.556 (7) | C5—H5A | 0.9300 |
C3—F4 | 1.327 (5) | C6—H6A | 0.9300 |
C3—F5 | 1.330 (5) | C8—H8A | 0.9300 |
C3—F6 | 1.333 (6) | C9—H9A | 0.9300 |
C4—C5 | 1.381 (6) | C12—H12A | 0.9300 |
C4—C9 | 1.390 (6) | C13—H13A | 0.9300 |
C5—C6 | 1.377 (6) | C15—H15A | 0.9300 |
C6—C7 | 1.383 (7) | C16—H16A | 0.9300 |
C1—C2—C3 | 108.6 (4) | C16—C11—C12 | 118.9 (4) |
C1—C2—C4 | 106.7 (4) | C16—C11—C2 | 118.5 (4) |
C1—C2—C11 | 112.9 (4) | C12—C11—C2 | 122.6 (4) |
C4—C2—C3 | 111.8 (4) | C13—C12—C11 | 119.4 (5) |
C4—C2—C11 | 111.6 (3) | C14—C13—C12 | 121.3 (4) |
C11—C2—C3 | 105.2 (3) | C13—C14—C15 | 118.8 (4) |
F3—C1—F2 | 106.7 (5) | C13—C14—C17 | 117.0 (5) |
F3—C1—F1 | 107.7 (5) | C15—C14—C17 | 124.2 (5) |
F2—C1—F1 | 106.1 (4) | C16—C15—C14 | 120.7 (5) |
F3—C1—C2 | 111.1 (4) | C15—C16—C11 | 121.0 (4) |
F2—C1—C2 | 111.4 (4) | O2—C17—C14 | 129.4 (6) |
F1—C1—C2 | 113.4 (5) | O2—C17—Cl2 | 114.7 (5) |
F4—C3—F5 | 106.9 (4) | C14—C17—Cl2 | 115.9 (4) |
F4—C3—F6 | 106.9 (4) | C10—Cl1—Cl2 | 82.75 (16) |
F5—C3—F6 | 106.8 (4) | C17—Cl2—Cl1 | 83.97 (19) |
F4—C3—C2 | 111.7 (4) | C6—C5—H5A | 119.4 |
F5—C3—C2 | 113.5 (4) | C4—C5—H5A | 119.4 |
F6—C3—C2 | 110.7 (4) | C5—C6—H6A | 119.9 |
C5—C4—C9 | 117.8 (4) | C7—C6—H6A | 119.9 |
C5—C4—C2 | 123.8 (4) | C7—C8—H8A | 119.9 |
C9—C4—C2 | 118.3 (4) | C9—C8—H8A | 119.9 |
C6—C5—C4 | 121.3 (4) | C8—C9—H9A | 119.4 |
C5—C6—C7 | 120.1 (4) | C4—C9—H9A | 119.4 |
C8—C7—C6 | 119.3 (4) | C13—C12—H12A | 120.3 |
C8—C7—C10 | 124.1 (4) | C11—C12—H12A | 120.3 |
C6—C7—C10 | 116.6 (4) | C14—C13—H13A | 119.4 |
C7—C8—C9 | 120.3 (4) | C12—C13—H13A | 119.4 |
C8—C9—C4 | 121.2 (4) | C16—C15—H15A | 119.7 |
O1—C10—C7 | 125.7 (5) | C14—C15—H15A | 119.7 |
O1—C10—Cl1 | 118.9 (4) | C15—C16—H16A | 119.5 |
C7—C10—Cl1 | 115.3 (4) | C11—C16—H16A | 119.5 |
F3—C1—C2—C4 | −71.4 (5) | C8—C7—C10—O1 | 175.9 (5) |
F2—C1—C2—C4 | 47.5 (6) | C6—C7—C10—O1 | −4.5 (7) |
F1—C1—C2—C4 | 167.1 (4) | C8—C7—C10—Cl1 | −3.8 (6) |
F3—C1—C2—C11 | 51.6 (5) | C6—C7—C10—Cl1 | 175.9 (4) |
F2—C1—C2—C11 | 170.4 (4) | C1—C2—C11—C16 | −163.6 (4) |
F1—C1—C2—C11 | −69.9 (6) | C4—C2—C11—C16 | −43.4 (5) |
F3—C1—C2—C3 | 167.9 (4) | C3—C2—C11—C16 | 78.0 (5) |
F2—C1—C2—C3 | −73.2 (5) | C1—C2—C11—C12 | 17.6 (6) |
F1—C1—C2—C3 | 46.4 (6) | C4—C2—C11—C12 | 137.8 (4) |
C1—C2—C3—F4 | −74.5 (5) | C3—C2—C11—C12 | −100.8 (5) |
C4—C2—C3—F4 | 167.9 (4) | C16—C11—C12—C13 | −0.2 (7) |
C11—C2—C3—F4 | 46.6 (5) | C2—C11—C12—C13 | 178.6 (4) |
C1—C2—C3—F5 | 46.4 (5) | C11—C12—C13—C14 | 0.8 (7) |
C4—C2—C3—F5 | −71.1 (5) | C12—C13—C14—C15 | −1.0 (7) |
C11—C2—C3—F5 | 167.6 (4) | C12—C13—C14—C17 | 178.1 (5) |
C1—C2—C3—F6 | 166.4 (4) | C13—C14—C15—C16 | 0.5 (7) |
C4—C2—C3—F6 | 48.9 (5) | C17—C14—C15—C16 | −178.5 (5) |
C11—C2—C3—F6 | −72.4 (4) | C14—C15—C16—C11 | 0.1 (7) |
C1—C2—C4—C5 | −92.4 (5) | C12—C11—C16—C15 | −0.3 (7) |
C11—C2—C4—C5 | 143.8 (4) | C2—C11—C16—C15 | −179.1 (4) |
C3—C2—C4—C5 | 26.2 (6) | C13—C14—C17—O2 | 6.1 (10) |
C1—C2—C4—C9 | 83.7 (5) | C15—C14—C17—O2 | −174.9 (7) |
C11—C2—C4—C9 | −40.0 (5) | C13—C14—C17—Cl2 | −174.8 (4) |
C3—C2—C4—C9 | −157.6 (4) | C15—C14—C17—Cl2 | 4.2 (7) |
C9—C4—C5—C6 | 2.2 (7) | C7—C10—O1—O2 | −36.8 (4) |
C2—C4—C5—C6 | 178.4 (4) | Cl1—C10—O1—O2 | 142.8 (8) |
C4—C5—C6—C7 | −0.2 (7) | C14—C17—O2—O1 | −39.5 (6) |
C5—C6—C7—C8 | −1.3 (7) | Cl2—C17—O2—O1 | 141.3 (11) |
C5—C6—C7—C10 | 179.0 (4) | C10—O1—O2—C17 | −136.2 (11) |
C6—C7—C8—C9 | 0.7 (7) | O1—C10—Cl1—Cl2 | −147.3 (4) |
C10—C7—C8—C9 | −179.7 (4) | C7—C10—Cl1—Cl2 | 32.3 (3) |
C7—C8—C9—C4 | 1.4 (7) | O2—C17—Cl2—Cl1 | −149.1 (6) |
C5—C4—C9—C8 | −2.9 (7) | C14—C17—Cl2—Cl1 | 31.6 (4) |
C2—C4—C9—C8 | −179.3 (4) | C10—Cl1—Cl2—C17 | −68.8 (3) |