3-(4-Fluoro-benzyl-idene)-1,5-dioxa-spiro-[5.5]undecane-2,4-dione.

In the title mol-ecule, C(16)H(15)FO(4), the fused 1,3-dioxane and cyclo-hexane rings exhibit a bath and a chair conformation, respectively. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For related structures, see: Zeng & Jian (2009 ▶); Zeng et al. (2009 ▶). For applications of spiro compounds, see: Jiang et al. (1998 ▶); Lian et al. (2008 ▶); Wei et al. (2008 ▶).

Experimental

Crystal data

C16H15FO4

M = 290.28

Triclinic,

a = 5.6690 (11) Å

b = 10.130 (2) Å

c = 12.160 (2) Å

α = 100.68 (3)°

β = 90.73 (3)°

γ = 91.20 (3)°

V = 686.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.25 × 0.18 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

6753 measured reflections

3124 independent reflections

2481 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.127

S = 1.11

3124 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810054395/cv5023sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054395/cv5023Isup2.hkl

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

C16H15FO4	Z = 2
Mr = 290.28	F(000) = 304
Triclinic, P1	Dx = 1.405 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6690 (11) Å	Cell parameters from 2481 reflections
b = 10.130 (2) Å	θ = 3.4–27.5°
c = 12.160 (2) Å	µ = 0.11 mm−1
α = 100.68 (3)°	T = 293 K
β = 90.73 (3)°	Block, colourless
γ = 91.20 (3)°	0.25 × 0.18 × 0.12 mm
V = 686.0 (2) Å3

Bruker SMART CCD area-detector diffractometer	2481 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
graphite	θmax = 27.5°, θmin = 3.4°
phi and ω scans	h = −6→7
6753 measured reflections	k = −13→13
3124 independent reflections	l = −15→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.075P)2 + 0.0414P] where P = (Fo2 + 2Fc2)/3
3124 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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 > 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
O4	0.41354 (13)	0.17850 (9)	0.73171 (7)	0.0412 (2)
O3	0.23315 (15)	0.01227 (9)	0.59454 (6)	0.0443 (2)
O2	0.54128 (17)	0.12738 (11)	0.89002 (8)	0.0566 (3)
O1	0.19126 (18)	−0.19449 (10)	0.62363 (8)	0.0542 (3)
C8	0.21663 (19)	−0.07730 (12)	0.66337 (10)	0.0397 (3)
F1	−0.52419 (17)	−0.46737 (10)	0.87835 (8)	0.0718 (3)
C7	0.41388 (19)	0.09907 (13)	0.80943 (9)	0.0390 (3)
C11	−0.0075 (2)	−0.18139 (12)	0.86756 (9)	0.0386 (3)
C9	0.25581 (19)	−0.02211 (12)	0.78410 (9)	0.0369 (3)
C4	0.23557 (19)	0.15348 (12)	0.64363 (9)	0.0373 (3)
C15	−0.3686 (2)	−0.29703 (14)	0.79341 (12)	0.0483 (3)
H15A	−0.4931	−0.3097	0.7417	0.058*
C10	0.1751 (2)	−0.07673 (12)	0.86916 (10)	0.0395 (3)
H10A	0.2448	−0.0435	0.9387	0.047*
C14	−0.3539 (2)	−0.37296 (13)	0.87486 (11)	0.0477 (3)
C5	−0.00563 (19)	0.19627 (13)	0.68678 (10)	0.0398 (3)
H5A	−0.0431	0.1530	0.7494	0.048*
H5B	−0.1233	0.1671	0.6282	0.048*
C16	−0.1937 (2)	−0.20081 (13)	0.78976 (11)	0.0446 (3)
H16A	−0.2004	−0.1483	0.7347	0.053*
C3	0.3168 (2)	0.22760 (16)	0.55360 (11)	0.0510 (3)
H3A	0.2194	0.1992	0.4869	0.061*
H3B	0.4783	0.2043	0.5348	0.061*
C13	−0.1757 (3)	−0.35709 (15)	0.95384 (11)	0.0526 (3)
H13A	−0.1711	−0.4106	1.0082	0.063*
C12	−0.0029 (2)	−0.25937 (14)	0.95053 (10)	0.0473 (3)
H12A	0.1176	−0.2457	1.0043	0.057*
C6	−0.0155 (2)	0.34786 (14)	0.72405 (12)	0.0522 (3)
H6A	−0.1749	0.3723	0.7460	0.063*
H6B	0.0879	0.3758	0.7887	0.063*
C2	0.3031 (3)	0.37944 (17)	0.59021 (14)	0.0625 (4)
H2A	0.4182	0.4098	0.6497	0.075*
H2B	0.3421	0.4226	0.5277	0.075*
C1	0.0590 (3)	0.42054 (17)	0.63108 (15)	0.0642 (4)
H1A	−0.0536	0.3997	0.5692	0.077*
H1B	0.0590	0.5168	0.6584	0.077*

	U11	U22	U33	U12	U13	U23
O4	0.0287 (4)	0.0539 (5)	0.0422 (4)	−0.0084 (3)	−0.0059 (3)	0.0136 (4)
O3	0.0462 (5)	0.0525 (5)	0.0318 (4)	0.0047 (4)	0.0000 (3)	0.0016 (4)
O2	0.0543 (5)	0.0664 (6)	0.0495 (5)	−0.0195 (5)	−0.0240 (4)	0.0156 (5)
O1	0.0602 (6)	0.0480 (5)	0.0484 (5)	−0.0020 (4)	0.0003 (4)	−0.0067 (4)
C8	0.0311 (5)	0.0475 (7)	0.0380 (6)	0.0005 (5)	0.0000 (4)	0.0010 (5)
F1	0.0644 (6)	0.0712 (6)	0.0810 (6)	−0.0309 (5)	−0.0030 (5)	0.0207 (5)
C7	0.0310 (5)	0.0482 (6)	0.0372 (6)	−0.0030 (5)	−0.0034 (4)	0.0074 (5)
C11	0.0361 (5)	0.0410 (6)	0.0376 (6)	0.0002 (4)	0.0015 (4)	0.0046 (5)
C9	0.0314 (5)	0.0411 (6)	0.0366 (5)	−0.0003 (4)	−0.0036 (4)	0.0034 (5)
C4	0.0291 (5)	0.0487 (6)	0.0333 (5)	−0.0018 (4)	−0.0031 (4)	0.0065 (5)
C15	0.0362 (6)	0.0545 (7)	0.0530 (7)	−0.0033 (5)	−0.0068 (5)	0.0078 (6)
C10	0.0369 (6)	0.0432 (6)	0.0372 (6)	−0.0014 (5)	−0.0047 (5)	0.0052 (5)
C14	0.0420 (6)	0.0451 (7)	0.0539 (7)	−0.0085 (5)	0.0047 (5)	0.0049 (6)
C5	0.0282 (5)	0.0493 (7)	0.0414 (6)	−0.0010 (5)	−0.0013 (4)	0.0077 (5)
C16	0.0383 (6)	0.0495 (7)	0.0481 (7)	0.0010 (5)	−0.0037 (5)	0.0152 (6)
C3	0.0416 (6)	0.0738 (9)	0.0413 (6)	−0.0025 (6)	0.0023 (5)	0.0203 (6)
C13	0.0590 (8)	0.0550 (8)	0.0468 (7)	−0.0084 (6)	−0.0006 (6)	0.0184 (6)
C12	0.0471 (7)	0.0560 (7)	0.0389 (6)	−0.0066 (6)	−0.0049 (5)	0.0098 (5)
C6	0.0469 (7)	0.0505 (7)	0.0573 (8)	0.0049 (6)	−0.0003 (6)	0.0047 (6)
C2	0.0610 (8)	0.0695 (10)	0.0644 (9)	−0.0146 (7)	−0.0041 (7)	0.0339 (8)
C1	0.0693 (9)	0.0531 (8)	0.0738 (10)	0.0022 (7)	−0.0094 (8)	0.0216 (7)

O4—C7	1.3500 (15)	C14—C13	1.371 (2)
O4—C4	1.4458 (13)	C5—C6	1.5208 (19)
O3—C8	1.3463 (16)	C5—H5A	0.9700
O3—C4	1.4440 (15)	C5—H5B	0.9700
O2—C7	1.1972 (14)	C16—H16A	0.9300
O1—C8	1.2008 (15)	C3—C2	1.524 (2)
C8—C9	1.4830 (16)	C3—H3A	0.9700
F1—C14	1.3511 (15)	C3—H3B	0.9700
C7—C9	1.4872 (16)	C13—C12	1.3845 (19)
C11—C12	1.3922 (17)	C13—H13A	0.9300
C11—C16	1.3948 (17)	C12—H12A	0.9300
C11—C10	1.4635 (17)	C6—C1	1.519 (2)
C9—C10	1.3411 (17)	C6—H6A	0.9700
C4—C3	1.5092 (18)	C6—H6B	0.9700
C4—C5	1.5138 (16)	C2—C1	1.517 (2)
C15—C14	1.365 (2)	C2—H2A	0.9700
C15—C16	1.3827 (18)	C2—H2B	0.9700
C15—H15A	0.9300	C1—H1A	0.9700
C10—H10A	0.9300	C1—H1B	0.9700
C7—O4—C4	118.46 (9)	H5A—C5—H5B	108.0
C8—O3—C4	118.15 (9)	C15—C16—C11	120.91 (12)
O1—C8—O3	119.04 (11)	C15—C16—H16A	119.5
O1—C8—C9	124.97 (12)	C11—C16—H16A	119.5
O3—C8—C9	115.69 (10)	C4—C3—C2	112.08 (12)
O2—C7—O4	119.51 (11)	C4—C3—H3A	109.2
O2—C7—C9	125.10 (12)	C2—C3—H3A	109.2
O4—C7—C9	115.36 (9)	C4—C3—H3B	109.2
C12—C11—C16	118.66 (11)	C2—C3—H3B	109.2
C12—C11—C10	118.86 (11)	H3A—C3—H3B	107.9
C16—C11—C10	122.37 (11)	C14—C13—C12	118.29 (13)
C10—C9—C8	125.84 (11)	C14—C13—H13A	120.9
C10—C9—C7	118.84 (10)	C12—C13—H13A	120.9
C8—C9—C7	115.16 (11)	C13—C12—C11	120.75 (12)
O3—C4—O4	108.60 (10)	C13—C12—H12A	119.6
O3—C4—C3	106.43 (10)	C11—C12—H12A	119.6
O4—C4—C3	106.66 (10)	C1—C6—C5	111.29 (12)
O3—C4—C5	110.87 (10)	C1—C6—H6A	109.4
O4—C4—C5	111.68 (9)	C5—C6—H6A	109.4
C3—C4—C5	112.35 (11)	C1—C6—H6B	109.4
C14—C15—C16	118.30 (12)	C5—C6—H6B	109.4
C14—C15—H15A	120.8	H6A—C6—H6B	108.0
C16—C15—H15A	120.8	C1—C2—C3	111.48 (13)
C9—C10—C11	128.90 (11)	C1—C2—H2A	109.3
C9—C10—H10A	115.6	C3—C2—H2A	109.3
C11—C10—H10A	115.6	C1—C2—H2B	109.3
F1—C14—C15	118.41 (12)	C3—C2—H2B	109.3
F1—C14—C13	118.51 (13)	H2A—C2—H2B	108.0
C15—C14—C13	123.08 (12)	C2—C1—C6	110.99 (13)
C4—C5—C6	111.58 (11)	C2—C1—H1A	109.4
C4—C5—H5A	109.3	C6—C1—H1A	109.4
C6—C5—H5A	109.3	C2—C1—H1B	109.4
C4—C5—H5B	109.3	C6—C1—H1B	109.4
C6—C5—H5B	109.3	H1A—C1—H1B	108.0

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O2i	0.93	2.47	3.3405 (17)	156
C10—H10A···O2	0.93	2.54	2.874 (2)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O2i	0.93	2.47	3.3405 (17)	156

Symmetry code: (i) .