3,3,4,4-Tetra-fluoro-2,3,4,5-tetra-hydro-1,6-benzodioxocine-8-carbaldehyde.

In the title compound, C(11)H(8)F(4)O(3), the eight-membered dialk-oxy ring adopts a highly puckered conformation. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions.

Related literature

For the applications of fluorinated mcarocyles, see: Babudri et al. (2007 ▶).

Experimental

Crystal data

C11H8F4O3

M = 264.17

Monoclinic,

a = 9.142 (5) Å

b = 11.4935 (14) Å

c = 10.928 (10) Å

β = 104.109 (15)°

V = 1113.6 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 298 K

0.35 × 0.24 × 0.11 mm

Data collection

Bruker SMART CCD diffractometer

5552 measured reflections

2000 independent reflections

972 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.146

S = 0.97

2000 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014133/hb5362sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014133/hb5362Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H8F4O3	F(000) = 536.0
Mr = 264.17	Dx = 1.576 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 733 reflections
a = 9.142 (5) Å	θ = 3.2–20.1°
b = 11.4935 (14) Å	µ = 0.16 mm−1
c = 10.928 (10) Å	T = 298 K
β = 104.109 (15)°	Block, colourless
V = 1113.6 (12) Å3	0.35 × 0.24 × 0.11 mm
Z = 4

Bruker SMART CCD diffractometer	972 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.044
graphite	θmax = 25.2°, θmin = 2.6°
ω scans	h = −6→10
5552 measured reflections	k = −13→13
2000 independent reflections	l = −13→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.146	w = 1/[σ2(Fo2) + (0.049P)2 + 0.4913P] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
2000 reflections	Δρmax = 0.14 e Å−3
164 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (12)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq
F2	0.5814 (2)	0.90137 (19)	0.9443 (2)	0.0901 (8)
F4	0.9709 (3)	0.8853 (2)	1.0613 (2)	0.1040 (9)
F1	0.7668 (3)	0.9585 (2)	0.8674 (2)	0.1008 (9)
F3	0.7960 (3)	0.9756 (2)	1.1293 (3)	0.1194 (10)
C4	0.8950 (4)	0.4731 (3)	1.1272 (3)	0.0599 (10)
H4	0.9789	0.4745	1.1953	0.072*
C7	0.6454 (3)	0.4699 (3)	0.9227 (3)	0.0545 (9)
H7	0.5614	0.4689	0.8547	0.065*
C6	0.7048 (3)	0.5746 (3)	0.9715 (3)	0.0535 (9)
C5	0.8301 (3)	0.5770 (3)	1.0754 (3)	0.0552 (9)
C2	0.7096 (3)	0.3650 (3)	0.9738 (3)	0.0549 (9)
C3	0.8354 (3)	0.3678 (3)	1.0779 (3)	0.0590 (10)
H3	0.8785	0.2986	1.1136	0.071*
C10	0.7221 (4)	0.8729 (4)	0.9373 (4)	0.0685 (11)
C8	0.8155 (4)	0.7738 (3)	1.1564 (3)	0.0669 (11)
H8A	0.8542	0.7957	1.2441	0.080*
H8B	0.7108	0.7509	1.1445	0.080*
C1	0.6488 (4)	0.2520 (4)	0.9223 (4)	0.0664 (11)
H1	0.6927	0.1853	0.9636	0.080*
C11	0.8265 (4)	0.8762 (4)	1.0718 (4)	0.0741 (11)
C9	0.7179 (4)	0.7596 (3)	0.8678 (3)	0.0657 (10)
H9A	0.6716	0.7710	0.7788	0.079*
H9B	0.8197	0.7310	0.8761	0.079*
O2	0.9011 (2)	0.6785 (2)	1.1261 (2)	0.0670 (7)
O1	0.6327 (2)	0.6767 (2)	0.9195 (2)	0.0622 (7)
O3	0.5453 (3)	0.2397 (2)	0.8295 (3)	0.0825 (9)

	U11	U22	U33	U12	U13	U23
F2	0.0728 (15)	0.0924 (18)	0.0987 (18)	0.0255 (13)	0.0085 (12)	0.0057 (14)
F4	0.0709 (15)	0.112 (2)	0.116 (2)	−0.0292 (14)	−0.0040 (13)	0.0202 (16)
F1	0.1117 (19)	0.0856 (18)	0.0951 (19)	−0.0162 (14)	0.0061 (14)	0.0252 (14)
F3	0.157 (2)	0.0757 (18)	0.103 (2)	0.0154 (16)	−0.0126 (17)	−0.0179 (16)
C4	0.049 (2)	0.073 (3)	0.046 (2)	−0.0005 (19)	−0.0088 (15)	0.0038 (19)
C7	0.0456 (19)	0.070 (3)	0.0410 (19)	−0.0046 (18)	−0.0020 (15)	0.0014 (18)
C6	0.0420 (19)	0.067 (3)	0.046 (2)	0.0014 (17)	0.0012 (16)	0.0051 (18)
C5	0.0449 (19)	0.065 (3)	0.049 (2)	−0.0042 (17)	−0.0011 (16)	−0.0010 (18)
C2	0.049 (2)	0.065 (2)	0.047 (2)	−0.0067 (17)	0.0062 (16)	−0.0003 (18)
C3	0.056 (2)	0.065 (3)	0.049 (2)	0.0014 (18)	0.0010 (17)	0.0049 (18)
C10	0.065 (2)	0.070 (3)	0.068 (3)	−0.003 (2)	0.010 (2)	0.013 (2)
C8	0.063 (2)	0.079 (3)	0.052 (2)	−0.001 (2)	0.0015 (17)	−0.009 (2)
C1	0.064 (2)	0.071 (3)	0.063 (2)	−0.010 (2)	0.012 (2)	−0.003 (2)
C11	0.070 (3)	0.071 (3)	0.074 (3)	0.000 (2)	0.004 (2)	−0.009 (2)
C9	0.058 (2)	0.084 (3)	0.049 (2)	0.000 (2)	0.0007 (16)	0.011 (2)
O2	0.0481 (13)	0.0678 (17)	0.0733 (18)	−0.0011 (12)	−0.0077 (12)	−0.0091 (13)
O1	0.0472 (13)	0.0663 (17)	0.0647 (16)	0.0009 (12)	−0.0025 (11)	0.0115 (13)
O3	0.0749 (17)	0.096 (2)	0.0663 (18)	−0.0205 (16)	−0.0032 (14)	−0.0142 (15)

F2—C10	1.347 (4)	C2—C1	1.469 (5)
F4—C11	1.357 (4)	C3—H3	0.9300
F1—C10	1.368 (4)	C10—C9	1.504 (5)
F3—C11	1.365 (4)	C10—C11	1.545 (6)
C4—C3	1.381 (4)	C8—O2	1.432 (4)
C4—C5	1.392 (4)	C8—C11	1.515 (5)
C4—H4	0.9300	C8—H8A	0.9700
C7—C6	1.374 (4)	C8—H8B	0.9700
C7—C2	1.397 (4)	C1—O3	1.215 (4)
C7—H7	0.9300	C1—H1	0.9300
C6—O1	1.398 (4)	C9—O1	1.430 (4)
C6—C5	1.402 (4)	C9—H9A	0.9700
C5—O2	1.383 (4)	C9—H9B	0.9700
C2—C3	1.407 (4)
C3—C4—C5	120.3 (3)	O2—C8—C11	109.4 (3)
C3—C4—H4	119.8	O2—C8—H8A	109.8
C5—C4—H4	119.8	C11—C8—H8A	109.8
C6—C7—C2	120.9 (3)	O2—C8—H8B	109.8
C6—C7—H7	119.6	C11—C8—H8B	109.8
C2—C7—H7	119.6	H8A—C8—H8B	108.3
C7—C6—O1	118.4 (3)	O3—C1—C2	124.6 (4)
C7—C6—C5	119.9 (3)	O3—C1—H1	117.7
O1—C6—C5	121.6 (3)	C2—C1—H1	117.7
O2—C5—C4	116.7 (3)	F4—C11—F3	106.6 (3)
O2—C5—C6	123.5 (3)	F4—C11—C8	108.8 (3)
C4—C5—C6	119.7 (3)	F3—C11—C8	108.5 (4)
C7—C2—C3	119.0 (3)	F4—C11—C10	108.1 (4)
C7—C2—C1	121.8 (3)	F3—C11—C10	108.1 (3)
C3—C2—C1	119.2 (3)	C8—C11—C10	116.4 (3)
C4—C3—C2	120.1 (3)	O1—C9—C10	109.0 (3)
C4—C3—H3	119.9	O1—C9—H9A	109.9
C2—C3—H3	119.9	C10—C9—H9A	109.9
F2—C10—F1	106.1 (3)	O1—C9—H9B	109.9
F2—C10—C9	109.4 (3)	C10—C9—H9B	109.9
F1—C10—C9	108.4 (3)	H9A—C9—H9B	108.3
F2—C10—C11	108.5 (4)	C5—O2—C8	120.5 (2)
F1—C10—C11	108.3 (3)	C6—O1—C9	118.1 (2)
C9—C10—C11	115.8 (3)
C2—C7—C6—O1	−177.7 (3)	F2—C10—C11—F4	−160.5 (3)
C2—C7—C6—C5	−1.1 (5)	F1—C10—C11—F4	−45.8 (4)
C3—C4—C5—O2	−176.8 (3)	C9—C10—C11—F4	76.1 (4)
C3—C4—C5—C6	−0.9 (5)	F2—C10—C11—F3	−45.4 (5)
C7—C6—C5—O2	176.6 (3)	F1—C10—C11—F3	69.2 (4)
O1—C6—C5—O2	−6.8 (5)	C9—C10—C11—F3	−168.8 (3)
C7—C6—C5—C4	1.0 (5)	F2—C10—C11—C8	76.9 (4)
O1—C6—C5—C4	177.6 (3)	F1—C10—C11—C8	−168.5 (3)
C6—C7—C2—C3	0.9 (5)	C9—C10—C11—C8	−46.5 (5)
C6—C7—C2—C1	−179.4 (3)	F2—C10—C9—O1	−48.7 (4)
C5—C4—C3—C2	0.8 (5)	F1—C10—C9—O1	−163.9 (2)
C7—C2—C3—C4	−0.8 (5)	C11—C10—C9—O1	74.2 (4)
C1—C2—C3—C4	179.5 (3)	C4—C5—O2—C8	−134.3 (3)
C7—C2—C1—O3	3.8 (6)	C6—C5—O2—C8	49.9 (5)
C3—C2—C1—O3	−176.6 (4)	C11—C8—O2—C5	−114.5 (3)
O2—C8—C11—F4	−41.8 (4)	C7—C6—O1—C9	−121.7 (3)
O2—C8—C11—F3	−157.5 (3)	C5—C6—O1—C9	61.7 (4)
O2—C8—C11—C10	80.4 (4)	C10—C9—O1—C6	−120.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.93	2.52	3.193 (5)	130
C8—H8B···O3ii	0.97	2.43	3.343 (6)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.93	2.52	3.193 (5)	130
C8—H8B⋯O3ii	0.97	2.43	3.343 (6)	157

Symmetry codes: (i) ; (ii) .