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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028236/sa2010sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028236/sa2010Isup2.hkl
Contains datablock I

CCDC reference: 618318

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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
C17H8Cl2F6O2F(000) = 1712
Mr = 429.13Dx = 1.650 Mg m3
Monoclinic, C2/cMelting point: 416 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 19.338 (9) ÅCell parameters from 56 reflections
b = 12.299 (4) Åθ = 4.7–12.4°
c = 14.677 (4) ŵ = 0.45 mm1
β = 98.12 (3)°T = 298 K
V = 3456 (2) Å3Needle, colourless
Z = 80.60 × 0.20 × 0.18 mm
Data collection top
Bruker P4
diffractometer
Rint = 0.031
Radiation source: fine-focus sealed tubeθmax = 25.4°, θmin = 2.1°
Graphite monochromatorh = 231
ω scansk = 114
3727 measured reflectionsl = 1717
3122 independent reflections3 standard reflections every 97 reflections
1830 reflections with I > 2σ(I) intensity decay: 6.4%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196H-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 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.41 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7100 (3)0.3099 (5)0.3006 (4)0.0761 (15)
C20.7030 (2)0.3310 (3)0.1969 (3)0.0535 (10)
C30.7038 (2)0.2199 (4)0.1463 (4)0.0680 (13)
C40.6335 (2)0.3917 (3)0.1701 (3)0.0504 (10)
C50.5709 (2)0.3407 (4)0.1397 (3)0.0618 (12)
H5A0.56980.26550.13330.074*
C60.5099 (2)0.3990 (4)0.1187 (3)0.0629 (12)
H6A0.46830.36320.09820.075*
C70.5105 (2)0.5109 (4)0.1281 (3)0.0559 (11)
C80.5721 (2)0.5627 (4)0.1603 (3)0.0584 (11)
H8A0.57290.63780.16740.070*
C90.6327 (2)0.5038 (4)0.1820 (3)0.0577 (11)
H9A0.67380.53970.20500.069*
C100.4426 (2)0.5677 (5)0.1025 (3)0.0677 (13)
C110.7653 (2)0.3956 (3)0.1689 (3)0.0509 (10)
C120.8292 (2)0.4053 (4)0.2261 (3)0.0652 (12)
H12A0.83530.37360.28420.078*
C130.8832 (2)0.4626 (4)0.1956 (4)0.0658 (13)
H13A0.92580.46820.23340.079*
C140.8749 (2)0.5110 (4)0.1106 (4)0.0632 (12)
C150.8115 (2)0.5006 (4)0.0545 (3)0.0632 (12)
H15A0.80530.53260.00350.076*
C160.7578 (2)0.4436 (4)0.0835 (3)0.0590 (11)
H16A0.71550.43730.04480.071*
C170.9346 (3)0.5727 (5)0.0860 (5)0.0878 (17)
O10.38988 (18)0.5265 (4)0.0704 (3)0.0918 (12)
O20.9919 (2)0.5810 (4)0.1262 (4)0.131 (2)
F10.76061 (17)0.2385 (3)0.3309 (2)0.0973 (11)
F20.65087 (17)0.2690 (3)0.3244 (2)0.0967 (10)
F30.72308 (16)0.4012 (3)0.3479 (2)0.0861 (9)
F40.76753 (15)0.1775 (2)0.1554 (2)0.0887 (10)
F50.66239 (16)0.1456 (2)0.1762 (3)0.0958 (11)
F60.68282 (15)0.2318 (2)0.0564 (2)0.0791 (8)
Cl10.44406 (8)0.70990 (13)0.12276 (12)0.0931 (5)
Cl20.92003 (11)0.6431 (2)0.01868 (14)0.1394 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.063 (3)0.085 (4)0.081 (4)0.011 (3)0.012 (3)0.024 (3)
C20.046 (2)0.052 (2)0.063 (3)0.0036 (19)0.0092 (19)0.002 (2)
C30.057 (3)0.055 (3)0.095 (4)0.002 (2)0.019 (3)0.004 (3)
C40.043 (2)0.051 (2)0.058 (3)0.0032 (18)0.0111 (18)0.002 (2)
C50.051 (2)0.052 (3)0.084 (3)0.009 (2)0.015 (2)0.000 (2)
C60.038 (2)0.076 (3)0.075 (3)0.007 (2)0.010 (2)0.003 (3)
C70.041 (2)0.072 (3)0.056 (3)0.003 (2)0.0145 (18)0.002 (2)
C80.050 (2)0.054 (3)0.074 (3)0.004 (2)0.016 (2)0.006 (2)
C90.044 (2)0.059 (3)0.070 (3)0.001 (2)0.009 (2)0.008 (2)
C100.050 (3)0.092 (4)0.064 (3)0.013 (3)0.020 (2)0.014 (3)
C110.041 (2)0.051 (2)0.062 (3)0.0028 (18)0.0109 (18)0.001 (2)
C120.047 (2)0.073 (3)0.073 (3)0.011 (2)0.000 (2)0.002 (3)
C130.040 (2)0.075 (3)0.081 (4)0.001 (2)0.001 (2)0.009 (3)
C140.043 (2)0.062 (3)0.087 (4)0.008 (2)0.015 (2)0.011 (3)
C150.053 (3)0.069 (3)0.067 (3)0.005 (2)0.007 (2)0.002 (2)
C160.040 (2)0.062 (3)0.074 (3)0.007 (2)0.002 (2)0.004 (2)
C170.064 (3)0.090 (4)0.114 (5)0.015 (3)0.026 (3)0.011 (4)
O10.0452 (19)0.122 (3)0.106 (3)0.004 (2)0.0026 (18)0.015 (3)
O20.053 (2)0.153 (4)0.178 (5)0.043 (3)0.018 (3)0.021 (4)
F10.086 (2)0.107 (2)0.098 (2)0.0335 (19)0.0096 (17)0.036 (2)
F20.083 (2)0.117 (3)0.095 (2)0.0035 (19)0.0323 (17)0.035 (2)
F30.083 (2)0.108 (2)0.0663 (18)0.0131 (18)0.0093 (15)0.0041 (18)
F40.0696 (18)0.0653 (17)0.132 (3)0.0194 (15)0.0169 (17)0.0050 (18)
F50.089 (2)0.0537 (16)0.150 (3)0.0063 (16)0.033 (2)0.0090 (18)
F60.0741 (18)0.0701 (18)0.093 (2)0.0044 (14)0.0123 (16)0.0206 (16)
Cl10.0748 (9)0.0898 (10)0.1158 (12)0.0315 (7)0.0170 (8)0.0113 (9)
Cl20.1214 (15)0.182 (2)0.1163 (15)0.0742 (15)0.0227 (11)0.0224 (14)
Geometric parameters (Å, º) top
C10—O11.176 (6)C7—C81.374 (6)
C10—Cl11.774 (6)C7—C101.488 (6)
C17—O21.184 (7)C8—C91.375 (6)
C17—Cl21.751 (7)C11—C161.374 (6)
C1—F31.326 (7)C11—C121.397 (6)
C1—F21.339 (6)C12—C131.386 (7)
C1—F11.343 (6)C13—C141.370 (7)
C1—C21.531 (7)C14—C151.383 (6)
C2—C41.539 (6)C14—C171.469 (7)
C2—C111.547 (6)C15—C161.371 (6)
C2—C31.556 (7)C5—H5A0.9300
C3—F41.327 (5)C6—H6A0.9300
C3—F51.330 (5)C8—H8A0.9300
C3—F61.333 (6)C9—H9A0.9300
C4—C51.381 (6)C12—H12A0.9300
C4—C91.390 (6)C13—H13A0.9300
C5—C61.377 (6)C15—H15A0.9300
C6—C71.383 (7)C16—H16A0.9300
C1—C2—C3108.6 (4)C16—C11—C12118.9 (4)
C1—C2—C4106.7 (4)C16—C11—C2118.5 (4)
C1—C2—C11112.9 (4)C12—C11—C2122.6 (4)
C4—C2—C3111.8 (4)C13—C12—C11119.4 (5)
C4—C2—C11111.6 (3)C14—C13—C12121.3 (4)
C11—C2—C3105.2 (3)C13—C14—C15118.8 (4)
F3—C1—F2106.7 (5)C13—C14—C17117.0 (5)
F3—C1—F1107.7 (5)C15—C14—C17124.2 (5)
F2—C1—F1106.1 (4)C16—C15—C14120.7 (5)
F3—C1—C2111.1 (4)C15—C16—C11121.0 (4)
F2—C1—C2111.4 (4)O2—C17—C14129.4 (6)
F1—C1—C2113.4 (5)O2—C17—Cl2114.7 (5)
F4—C3—F5106.9 (4)C14—C17—Cl2115.9 (4)
F4—C3—F6106.9 (4)C10—Cl1—Cl282.75 (16)
F5—C3—F6106.8 (4)C17—Cl2—Cl183.97 (19)
F4—C3—C2111.7 (4)C6—C5—H5A119.4
F5—C3—C2113.5 (4)C4—C5—H5A119.4
F6—C3—C2110.7 (4)C5—C6—H6A119.9
C5—C4—C9117.8 (4)C7—C6—H6A119.9
C5—C4—C2123.8 (4)C7—C8—H8A119.9
C9—C4—C2118.3 (4)C9—C8—H8A119.9
C6—C5—C4121.3 (4)C8—C9—H9A119.4
C5—C6—C7120.1 (4)C4—C9—H9A119.4
C8—C7—C6119.3 (4)C13—C12—H12A120.3
C8—C7—C10124.1 (4)C11—C12—H12A120.3
C6—C7—C10116.6 (4)C14—C13—H13A119.4
C7—C8—C9120.3 (4)C12—C13—H13A119.4
C8—C9—C4121.2 (4)C16—C15—H15A119.7
O1—C10—C7125.7 (5)C14—C15—H15A119.7
O1—C10—Cl1118.9 (4)C15—C16—H16A119.5
C7—C10—Cl1115.3 (4)C11—C16—H16A119.5
F3—C1—C2—C471.4 (5)C8—C7—C10—O1175.9 (5)
F2—C1—C2—C447.5 (6)C6—C7—C10—O14.5 (7)
F1—C1—C2—C4167.1 (4)C8—C7—C10—Cl13.8 (6)
F3—C1—C2—C1151.6 (5)C6—C7—C10—Cl1175.9 (4)
F2—C1—C2—C11170.4 (4)C1—C2—C11—C16163.6 (4)
F1—C1—C2—C1169.9 (6)C4—C2—C11—C1643.4 (5)
F3—C1—C2—C3167.9 (4)C3—C2—C11—C1678.0 (5)
F2—C1—C2—C373.2 (5)C1—C2—C11—C1217.6 (6)
F1—C1—C2—C346.4 (6)C4—C2—C11—C12137.8 (4)
C1—C2—C3—F474.5 (5)C3—C2—C11—C12100.8 (5)
C4—C2—C3—F4167.9 (4)C16—C11—C12—C130.2 (7)
C11—C2—C3—F446.6 (5)C2—C11—C12—C13178.6 (4)
C1—C2—C3—F546.4 (5)C11—C12—C13—C140.8 (7)
C4—C2—C3—F571.1 (5)C12—C13—C14—C151.0 (7)
C11—C2—C3—F5167.6 (4)C12—C13—C14—C17178.1 (5)
C1—C2—C3—F6166.4 (4)C13—C14—C15—C160.5 (7)
C4—C2—C3—F648.9 (5)C17—C14—C15—C16178.5 (5)
C11—C2—C3—F672.4 (4)C14—C15—C16—C110.1 (7)
C1—C2—C4—C592.4 (5)C12—C11—C16—C150.3 (7)
C11—C2—C4—C5143.8 (4)C2—C11—C16—C15179.1 (4)
C3—C2—C4—C526.2 (6)C13—C14—C17—O26.1 (10)
C1—C2—C4—C983.7 (5)C15—C14—C17—O2174.9 (7)
C11—C2—C4—C940.0 (5)C13—C14—C17—Cl2174.8 (4)
C3—C2—C4—C9157.6 (4)C15—C14—C17—Cl24.2 (7)
C9—C4—C5—C62.2 (7)C7—C10—O1—O236.8 (4)
C2—C4—C5—C6178.4 (4)Cl1—C10—O1—O2142.8 (8)
C4—C5—C6—C70.2 (7)C14—C17—O2—O139.5 (6)
C5—C6—C7—C81.3 (7)Cl2—C17—O2—O1141.3 (11)
C5—C6—C7—C10179.0 (4)C10—O1—O2—C17136.2 (11)
C6—C7—C8—C90.7 (7)O1—C10—Cl1—Cl2147.3 (4)
C10—C7—C8—C9179.7 (4)C7—C10—Cl1—Cl232.3 (3)
C7—C8—C9—C41.4 (7)O2—C17—Cl2—Cl1149.1 (6)
C5—C4—C9—C82.9 (7)C14—C17—Cl2—Cl131.6 (4)
C2—C4—C9—C8179.3 (4)C10—Cl1—Cl2—C1768.8 (3)
 

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