2,2-Bis(penta­fluoro­phen­yloxy)-1,3-benzodioxole

Betz, R.; Klüfers, P.; Reichvilser, M.M.

doi:10.1107/S1600536807038950

2,2-Bis(pentafluorophenyloxy)-1,3-benzodioxole

R. Betz, P. Klüfers and M. M. Reichvilser

The title compound, C₁₉H₄F₁₀O₄, an orthocarbonate of a vicincal aromatic diol and two monofunctional aromatic alcohols, was prepared for the purpose of collecting NMR data on orthocarbonates and for comparison with similar silicon compounds. The molecule does not exhibit any crystallographic symmetry. The fused ring system is almost perfectly planar. The angle between the least-squares planes through the pentafluorophenyl groups is 81.26 (6)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038950/bg2082sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038950/bg2082Isup2.hkl Contains datablock I

CCDC reference: 660259

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Key indicators

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.003 Å
R factor = 0.051
wR factor = 0.133
Data-to-parameter ratio = 13.6

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No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    F26    -   C26     ..       5.39 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   0 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 title compound, C₁₉H₄F₁₀O₄, an orthocarbonate of a vicincal aromatic diol and two monofunctional aromatic alcohols, was prepared for the purpose of collecting NMR data on orthocarbonates and for comparison with similar silicon compounds. The molecular structure is shown in Fig. 1. The molecule does not exhibit any crystallographic symmetry.

The molecular packing is shown in Fig. 2.

Related literature top

For related literature, see: Gross et al. (1964), Komatsu et al. (1992), Mues & Buysch (1990).

Experimental top

2,2-Dichlorobenzo[1,3]dioxole was prepared according to Komatsu et al. (1992).

To a colorless solution of pentafluorophenol (1.84 g, 10.0 mmol) and pyridine (0.91 ml, 10.0 mmol) in dichloromethane, 2,2-dichlorobenzo[1,3]dioxole (0.96 g, 5.00 mmol) was added dropwise within 20 min at room temperature. The yellow reaction mixture was stirred over night and subsequently washed twice with water (5 ml). The organic phase was dried over Na₂SO₄. Removal of the solvent under reduced pressure afforded colorless crystals suitable for X-ray diffraction.

Structure description top

The title compound, C₁₉H₄F₁₀O₄, an orthocarbonate of a vicincal aromatic diol and two monofunctional aromatic alcohols, was prepared for the purpose of collecting NMR data on orthocarbonates and for comparison with similar silicon compounds. The molecular structure is shown in Fig. 1. The molecule does not exhibit any crystallographic symmetry.

The molecular packing is shown in Fig. 2.

For related literature, see: Gross et al. (1964), Komatsu et al. (1992), Mues & Buysch (1990).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
	Fig. 2. The packing of (I), viewed along [0 1 0]. H atoms omitted for clarity.

2,2-Bis(pentafluorophenyloxy)-1,3-benzodioxole top

Crystal data top

C₁₉H₄F₁₀O₄	Z = 4
M_r = 486.22	F(000) = 960
Monoclinic, P2₁/c	D_x = 1.833 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.8249 (15) Å	θ = 3.9–27.5°
b = 6.3560 (7) Å	µ = 0.20 mm⁻¹
c = 18.0213 (19) Å	T = 200 K
β = 103.552 (9)°	Platelet, colourless
V = 1762.2 (3) Å³	0.30 × 0.25 × 0.10 mm

Data collection top

Oxford XCalibur3 diffractometer	2950 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 27.5°, θ_min = 4.0°
Detector resolution: 15.9809 pixels mm^-1	h = −20→19
ω scans	k = −6→8
9833 measured reflections	l = −19→23
4059 independent 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)] = 0.051	Hydrogen site location: difference Fourier map
wR(F²) = 0.133	Only H-atom displacement parameters refined
S = 1.12	w = 1/[σ²(F_o²) + (0.0621P)² + 0.0854P] where P = (F_o² + 2F_c²)/3
4059 reflections	(Δ/σ)_max < 0.001
299 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₉H₄F₁₀O₄	V = 1762.2 (3) Å³
M_r = 486.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.8249 (15) Å	µ = 0.20 mm⁻¹
b = 6.3560 (7) Å	T = 200 K
c = 18.0213 (19) Å	0.30 × 0.25 × 0.10 mm
β = 103.552 (9)°

Data collection top

Oxford XCalibur3 diffractometer	2950 reflections with I > 2σ(I)
9833 measured reflections	R_int = 0.039
4059 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.133	Only H-atom displacement parameters refined
S = 1.12	Δρ_max = 0.25 e Å⁻³
4059 reflections	Δρ_min = −0.25 e Å⁻³
299 parameters

Special details top

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 > 2σ(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
F22	0.41079 (9)	0.4138 (2)	0.40677 (7)	0.0534 (4)
F23	0.36927 (10)	0.6908 (2)	0.50644 (8)	0.0583 (4)
F24	0.24267 (10)	0.5935 (2)	0.57956 (7)	0.0621 (4)
F25	0.16335 (9)	0.2136 (3)	0.55760 (8)	0.0645 (4)
F26	0.20458 (9)	−0.0631 (2)	0.45812 (8)	0.0537 (4)
F32	0.17016 (9)	−0.3524 (2)	0.18969 (8)	0.0537 (4)
F33	0.03388 (11)	−0.3142 (2)	0.06818 (8)	0.0669 (4)
F34	−0.06615 (9)	0.0375 (3)	0.05095 (8)	0.0692 (5)
F35	−0.02976 (9)	0.3499 (3)	0.15615 (9)	0.0669 (4)
F36	0.10328 (9)	0.3085 (2)	0.27928 (8)	0.0536 (4)
O11	0.33597 (9)	−0.0712 (2)	0.26222 (8)	0.0363 (3)
O12	0.27790 (8)	0.2504 (2)	0.27465 (7)	0.0345 (3)
O21	0.33313 (9)	0.0340 (2)	0.37940 (7)	0.0382 (4)
O31	0.20663 (9)	−0.0460 (2)	0.30080 (8)	0.0396 (4)
C10	0.28688 (13)	0.0447 (3)	0.30304 (11)	0.0344 (4)
C11	0.37378 (12)	0.0758 (3)	0.22285 (10)	0.0309 (4)
C12	0.33733 (12)	0.2693 (3)	0.22866 (10)	0.0302 (4)
C13	0.35747 (13)	0.4440 (3)	0.19270 (11)	0.0350 (5)
H13	0.3308	0.5763	0.1964	0.045 (3)*
C14	0.41999 (14)	0.4165 (3)	0.14986 (11)	0.0376 (5)
H14	0.4363	0.5332	0.1234	0.045 (3)*
C15	0.45836 (13)	0.2231 (3)	0.14539 (11)	0.0389 (5)
H15	0.5012	0.2105	0.1164	0.045 (3)*
C16	0.43601 (13)	0.0461 (3)	0.18213 (11)	0.0356 (5)
H16	0.4623	−0.0871	0.1792	0.045 (3)*
C21	0.30653 (13)	0.1741 (3)	0.42810 (11)	0.0340 (4)
C22	0.34749 (14)	0.3668 (4)	0.44189 (11)	0.0389 (5)
C23	0.32660 (15)	0.5076 (3)	0.49263 (12)	0.0415 (5)
C24	0.26363 (14)	0.4560 (4)	0.53031 (11)	0.0430 (5)
C25	0.22338 (13)	0.2641 (4)	0.51871 (11)	0.0429 (5)
C26	0.24407 (13)	0.1229 (3)	0.46800 (11)	0.0375 (5)
C31	0.14188 (13)	−0.0184 (3)	0.23495 (11)	0.0361 (5)
C32	0.12212 (14)	−0.1776 (3)	0.18163 (12)	0.0385 (5)
C33	0.05235 (15)	−0.1581 (4)	0.11929 (12)	0.0446 (5)
C34	0.00212 (14)	0.0198 (4)	0.11078 (12)	0.0469 (6)
C35	0.02027 (13)	0.1788 (4)	0.16381 (13)	0.0440 (5)
C36	0.08919 (14)	0.1574 (3)	0.22622 (12)	0.0387 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F22	0.0534 (8)	0.0631 (9)	0.0501 (8)	−0.0205 (7)	0.0252 (6)	−0.0057 (6)
F23	0.0757 (10)	0.0471 (8)	0.0478 (8)	−0.0076 (7)	0.0054 (7)	−0.0079 (6)
F24	0.0733 (10)	0.0760 (10)	0.0378 (7)	0.0270 (8)	0.0146 (7)	−0.0054 (7)
F25	0.0525 (8)	0.0986 (12)	0.0504 (8)	0.0076 (8)	0.0282 (7)	0.0167 (8)
F26	0.0499 (8)	0.0589 (9)	0.0522 (8)	−0.0133 (7)	0.0119 (6)	0.0103 (6)
F32	0.0575 (8)	0.0385 (7)	0.0650 (9)	0.0036 (7)	0.0142 (7)	−0.0011 (6)
F33	0.0786 (10)	0.0677 (10)	0.0499 (9)	−0.0208 (8)	0.0057 (7)	−0.0175 (7)
F34	0.0436 (8)	0.1070 (13)	0.0490 (8)	−0.0041 (9)	−0.0053 (6)	0.0108 (8)
F35	0.0519 (8)	0.0794 (10)	0.0721 (10)	0.0301 (8)	0.0201 (7)	0.0133 (8)
F36	0.0542 (8)	0.0583 (8)	0.0525 (8)	0.0079 (7)	0.0213 (6)	−0.0149 (6)
O11	0.0443 (8)	0.0282 (7)	0.0383 (8)	0.0023 (6)	0.0132 (6)	−0.0004 (6)
O12	0.0360 (7)	0.0324 (7)	0.0371 (8)	0.0036 (6)	0.0124 (6)	−0.0003 (6)
O21	0.0382 (8)	0.0435 (8)	0.0315 (8)	0.0035 (7)	0.0052 (6)	−0.0016 (6)
O31	0.0367 (7)	0.0467 (9)	0.0344 (8)	−0.0048 (7)	0.0061 (6)	0.0047 (6)
C10	0.0340 (10)	0.0361 (11)	0.0330 (10)	0.0019 (9)	0.0077 (8)	0.0003 (8)
C11	0.0316 (10)	0.0291 (10)	0.0295 (10)	−0.0001 (8)	0.0022 (7)	−0.0043 (7)
C12	0.0286 (9)	0.0336 (10)	0.0275 (10)	0.0009 (8)	0.0046 (7)	−0.0054 (7)
C13	0.0365 (10)	0.0310 (10)	0.0357 (10)	0.0031 (9)	0.0049 (8)	−0.0023 (8)
C14	0.0414 (11)	0.0377 (11)	0.0340 (11)	−0.0031 (10)	0.0095 (8)	−0.0006 (8)
C15	0.0362 (11)	0.0478 (12)	0.0345 (11)	0.0029 (10)	0.0118 (8)	−0.0046 (9)
C16	0.0351 (10)	0.0361 (11)	0.0350 (11)	0.0060 (9)	0.0066 (8)	−0.0062 (8)
C21	0.0322 (10)	0.0411 (11)	0.0282 (10)	0.0019 (9)	0.0060 (8)	0.0020 (8)
C22	0.0395 (11)	0.0493 (12)	0.0290 (10)	−0.0045 (10)	0.0101 (8)	0.0015 (9)
C23	0.0479 (12)	0.0402 (12)	0.0328 (11)	0.0009 (11)	0.0022 (9)	0.0008 (9)
C24	0.0470 (12)	0.0544 (14)	0.0270 (10)	0.0149 (11)	0.0073 (9)	0.0011 (9)
C25	0.0359 (11)	0.0656 (15)	0.0295 (11)	0.0086 (11)	0.0123 (8)	0.0125 (10)
C26	0.0344 (10)	0.0437 (12)	0.0324 (11)	−0.0035 (10)	0.0035 (8)	0.0093 (9)
C31	0.0311 (10)	0.0476 (12)	0.0308 (10)	−0.0016 (10)	0.0100 (8)	0.0028 (9)
C32	0.0377 (11)	0.0403 (12)	0.0398 (12)	−0.0033 (10)	0.0135 (9)	0.0011 (9)
C33	0.0429 (12)	0.0562 (14)	0.0353 (12)	−0.0120 (11)	0.0104 (9)	−0.0034 (10)
C34	0.0318 (10)	0.0709 (16)	0.0372 (12)	−0.0043 (11)	0.0067 (9)	0.0091 (11)
C35	0.0319 (10)	0.0552 (14)	0.0482 (13)	0.0096 (11)	0.0159 (9)	0.0081 (11)
C36	0.0391 (11)	0.0450 (12)	0.0361 (11)	0.0010 (10)	0.0168 (9)	−0.0033 (9)

Geometric parameters (Å, º) top

F22—C22	1.338 (2)	C12—C13	1.361 (3)
F23—C23	1.340 (3)	C13—C14	1.401 (3)
F24—C24	1.341 (2)	C13—H13	0.9500
F25—C25	1.345 (2)	C14—C15	1.382 (3)
F26—C26	1.330 (2)	C14—H14	0.9500
F32—C32	1.334 (2)	C15—C16	1.392 (3)
F33—C33	1.339 (3)	C15—H15	0.9500
F34—C34	1.340 (3)	C16—H16	0.9500
F35—C35	1.333 (2)	C21—C22	1.381 (3)
F36—C36	1.337 (2)	C21—C26	1.390 (3)
O11—C11	1.390 (2)	C22—C23	1.374 (3)
O11—C10	1.399 (2)	C23—C24	1.371 (3)
O12—C12	1.397 (2)	C24—C25	1.369 (3)
O12—C10	1.399 (2)	C25—C26	1.374 (3)
O21—C21	1.383 (2)	C31—C32	1.380 (3)
O21—C10	1.401 (2)	C31—C36	1.381 (3)
O31—C31	1.385 (2)	C32—C33	1.384 (3)
O31—C10	1.387 (2)	C33—C34	1.370 (3)
C11—C16	1.372 (3)	C34—C35	1.374 (3)
C11—C12	1.373 (3)	C35—C36	1.378 (3)

C11—O11—C10	105.85 (14)	F22—C22—C21	118.99 (19)
C12—O12—C10	105.80 (14)	C23—C22—C21	121.41 (19)
C21—O21—C10	115.16 (15)	F23—C23—C24	120.6 (2)
C31—O31—C10	117.43 (15)	F23—C23—C22	120.0 (2)
O31—C10—O11	112.53 (16)	C24—C23—C22	119.4 (2)
O31—C10—O12	111.37 (16)	F24—C24—C25	120.2 (2)
O11—C10—O12	108.74 (15)	F24—C24—C23	119.6 (2)
O31—C10—O21	105.81 (15)	C25—C24—C23	120.2 (2)
O11—C10—O21	105.33 (15)	F25—C25—C24	119.5 (2)
O12—C10—O21	112.94 (16)	F25—C25—C26	119.9 (2)
C16—C11—C12	122.06 (18)	C24—C25—C26	120.56 (19)
C16—C11—O11	129.01 (17)	F26—C26—C25	119.47 (19)
C12—C11—O11	108.91 (16)	F26—C26—C21	120.50 (19)
C13—C12—C11	123.04 (18)	C25—C26—C21	120.0 (2)
C13—C12—O12	128.17 (17)	C32—C31—C36	118.80 (19)
C11—C12—O12	108.78 (16)	C32—C31—O31	120.32 (19)
C12—C13—C14	115.80 (18)	C36—C31—O31	120.39 (18)
C12—C13—H13	122.1	F32—C32—C31	120.28 (18)
C14—C13—H13	122.1	F32—C32—C33	119.27 (19)
C15—C14—C13	121.31 (19)	C31—C32—C33	120.5 (2)
C15—C14—H14	119.3	F33—C33—C34	120.5 (2)
C13—C14—H14	119.3	F33—C33—C32	119.7 (2)
C14—C15—C16	121.79 (18)	C34—C33—C32	119.8 (2)
C14—C15—H15	119.1	F34—C34—C33	119.8 (2)
C16—C15—H15	119.1	F34—C34—C35	119.7 (2)
C11—C16—C15	115.97 (18)	C33—C34—C35	120.5 (2)
C11—C16—H16	122.0	F35—C35—C34	120.38 (19)
C15—C16—H16	122.0	F35—C35—C36	120.2 (2)
C22—C21—O21	119.04 (17)	C34—C35—C36	119.4 (2)
C22—C21—C26	118.37 (19)	F36—C36—C35	118.72 (19)
O21—C21—C26	122.43 (19)	F36—C36—C31	120.32 (19)
F22—C22—C23	119.6 (2)	C35—C36—C31	120.94 (19)

Experimental details

Crystal data
Chemical formula	C₁₉H₄F₁₀O₄
M_r	486.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	15.8249 (15), 6.3560 (7), 18.0213 (19)
β (°)	103.552 (9)
V (Å³)	1762.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.25 × 0.10

Data collection
Diffractometer	Oxford XCalibur3
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9833, 4059, 2950
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.133, 1.12
No. of reflections	4059
No. of parameters	299
H-atom treatment	Only H-atom displacement parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.25

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97.

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2,2-Bis(penta­fluoro­phen­yloxy)-1,3-benzodioxole

Supporting information

Key indicators

checkCIF/PLATON results

2,2-Bis(pentafluorophenyloxy)-1,3-benzodioxole