5-(2-Fluoro-benzyl-idene)-2,2-dimethyl-1,3-dioxane-4,6-dione.

The title compound, C(13)H(11)FO(4), was prepared by the reaction of 2,2-dimethyl-1,3-dioxane-4,6-dione and 2-fluoro-benzaldehyde in ethanol. In the crystal structure, mol-ecules are linked into chains by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For background to the use of Meldrum’s acid as a reagent in organic synthesis, see: Kuhn et al. (2003 ▶); Casadesus et al. (2006 ▶).

Experimental

Crystal data

C13H11FO4

M = 250.22

Triclinic,

a = 5.9907 (12) Å

b = 7.6135 (15) Å

c = 13.712 (3) Å

α = 104.66 (3)°

β = 97.00 (3)°

γ = 98.50 (3)°

V = 590.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.18 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

5846 measured reflections

2680 independent reflections

2232 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.122

S = 1.09

2680 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.21 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809038811/lh2910sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038811/lh2910Isup2.hkl

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

C13H11FO4	Z = 2
Mr = 250.22	F(000) = 260
Triclinic, P1	Dx = 1.408 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9907 (12) Å	Cell parameters from 2680 reflections
b = 7.6135 (15) Å	θ = 3.1–27.5°
c = 13.712 (3) Å	µ = 0.12 mm−1
α = 104.66 (3)°	T = 293 K
β = 97.00 (3)°	Block, colorless
γ = 98.50 (3)°	0.18 × 0.15 × 0.10 mm
V = 590.0 (2) Å3

Bruker SMART CCD diffractometer	2232 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
graphite	θmax = 27.5°, θmin = 3.1°
φ and ω scans	h = −7→7
5846 measured reflections	k = −9→9
2680 independent reflections	l = −17→17

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) = 0.122	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0689P)2 + 0.0762P] where P = (Fo2 + 2Fc2)/3
2680 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.21 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	0.24998 (15)	0.52398 (12)	0.08949 (6)	0.0433 (2)
F	−0.21328 (14)	0.74829 (12)	0.22191 (7)	0.0610 (3)
O3	0.42130 (16)	0.39182 (13)	0.21066 (7)	0.0487 (2)
O2	0.19470 (18)	0.81052 (13)	0.13437 (7)	0.0532 (3)
C10	0.22839 (19)	0.67636 (17)	0.16038 (9)	0.0387 (3)
O1	0.5140 (2)	0.54637 (16)	0.37345 (8)	0.0694 (4)
C4	0.0848 (2)	0.93620 (17)	0.35028 (9)	0.0418 (3)
C11	0.2576 (2)	0.35465 (17)	0.11792 (9)	0.0413 (3)
C7	0.2194 (2)	0.78997 (18)	0.34775 (9)	0.0436 (3)
H7A	0.2780	0.7790	0.4115	0.052*
C9	0.2713 (2)	0.66953 (16)	0.26804 (9)	0.0390 (3)
C6	−0.2546 (2)	1.0510 (2)	0.29876 (11)	0.0521 (3)
H6A	−0.3967	1.0306	0.2578	0.063*
C5	−0.1258 (2)	0.91420 (18)	0.29004 (9)	0.0430 (3)
C8	0.4099 (2)	0.53311 (18)	0.29079 (10)	0.0455 (3)
C3	0.1648 (3)	1.1072 (2)	0.42261 (11)	0.0547 (4)
H3A	0.3034	1.1261	0.4660	0.066*
C13	0.3522 (3)	0.2316 (2)	0.03544 (11)	0.0592 (4)
H13A	0.5007	0.2923	0.0301	0.089*
H13B	0.2516	0.2058	−0.0286	0.089*
H13C	0.3649	0.1179	0.0520	0.089*
C2	0.0417 (3)	1.2483 (2)	0.43080 (12)	0.0613 (4)
H2A	0.1004	1.3627	0.4775	0.074*
C1	−0.1683 (3)	1.2195 (2)	0.36964 (12)	0.0582 (4)
H1A	−0.2522	1.3141	0.3762	0.070*
C12	0.0242 (3)	0.2714 (2)	0.13214 (12)	0.0566 (4)
H12A	−0.0266	0.3564	0.1856	0.085*
H12B	0.0317	0.1583	0.1503	0.085*
H12C	−0.0815	0.2462	0.0696	0.085*

	U11	U22	U33	U12	U13	U23
O4	0.0517 (5)	0.0425 (5)	0.0385 (4)	0.0132 (4)	0.0100 (4)	0.0124 (4)
F	0.0480 (5)	0.0557 (5)	0.0669 (5)	0.0051 (4)	−0.0003 (4)	0.0021 (4)
O3	0.0514 (5)	0.0451 (5)	0.0475 (5)	0.0221 (4)	−0.0027 (4)	0.0065 (4)
O2	0.0690 (6)	0.0492 (5)	0.0510 (5)	0.0235 (5)	0.0113 (4)	0.0233 (4)
C10	0.0364 (5)	0.0409 (6)	0.0410 (6)	0.0114 (5)	0.0064 (5)	0.0129 (5)
O1	0.0878 (8)	0.0677 (7)	0.0492 (6)	0.0420 (6)	−0.0159 (5)	0.0068 (5)
C4	0.0452 (6)	0.0436 (7)	0.0389 (6)	0.0171 (5)	0.0077 (5)	0.0103 (5)
C11	0.0442 (6)	0.0387 (6)	0.0402 (6)	0.0099 (5)	0.0034 (5)	0.0098 (5)
C7	0.0463 (6)	0.0461 (7)	0.0387 (6)	0.0170 (5)	0.0013 (5)	0.0100 (5)
C9	0.0390 (6)	0.0393 (6)	0.0394 (6)	0.0128 (5)	0.0017 (5)	0.0114 (5)
C6	0.0409 (6)	0.0620 (9)	0.0593 (8)	0.0191 (6)	0.0085 (6)	0.0218 (7)
C5	0.0411 (6)	0.0440 (7)	0.0440 (6)	0.0089 (5)	0.0080 (5)	0.0110 (5)
C8	0.0485 (7)	0.0431 (7)	0.0441 (6)	0.0183 (5)	−0.0014 (5)	0.0092 (5)
C3	0.0550 (8)	0.0542 (8)	0.0479 (7)	0.0200 (6)	−0.0012 (6)	0.0007 (6)
C13	0.0701 (9)	0.0534 (8)	0.0528 (8)	0.0230 (7)	0.0137 (7)	0.0042 (6)
C2	0.0728 (10)	0.0465 (8)	0.0605 (8)	0.0221 (7)	0.0086 (7)	0.0022 (6)
C1	0.0653 (9)	0.0537 (8)	0.0661 (9)	0.0319 (7)	0.0188 (7)	0.0200 (7)
C12	0.0525 (8)	0.0538 (8)	0.0599 (8)	−0.0008 (6)	0.0093 (6)	0.0155 (6)

O4—C10	1.3460 (15)	C9—C8	1.4904 (17)
O4—C11	1.4434 (15)	C6—C5	1.3753 (19)
F—C5	1.3529 (16)	C6—C1	1.381 (2)
O3—C8	1.3457 (16)	C6—H6A	0.9300
O3—C11	1.4460 (15)	C3—C2	1.380 (2)
O2—C10	1.1996 (15)	C3—H3A	0.9300
C10—C9	1.4826 (16)	C13—H13A	0.9600
O1—C8	1.1979 (16)	C13—H13B	0.9600
C4—C5	1.3843 (18)	C13—H13C	0.9600
C4—C3	1.3978 (19)	C2—C1	1.379 (2)
C4—C7	1.4639 (17)	C2—H2A	0.9300
C11—C13	1.5018 (18)	C1—H1A	0.9300
C11—C12	1.5041 (19)	C12—H12A	0.9600
C7—C9	1.3385 (17)	C12—H12B	0.9600
C7—H7A	0.9300	C12—H12C	0.9600
C10—O4—C11	119.32 (9)	C6—C5—C4	123.07 (13)
C8—O3—C11	118.75 (9)	O1—C8—O3	119.85 (12)
O2—C10—O4	119.30 (11)	O1—C8—C9	124.13 (12)
O2—C10—C9	124.62 (11)	O3—C8—C9	115.98 (11)
O4—C10—C9	115.80 (10)	C2—C3—C4	121.18 (14)
C5—C4—C3	116.79 (12)	C2—C3—H3A	119.4
C5—C4—C7	124.51 (12)	C4—C3—H3A	119.4
C3—C4—C7	118.56 (12)	C11—C13—H13A	109.5
O4—C11—O3	109.41 (10)	C11—C13—H13B	109.5
O4—C11—C13	106.34 (11)	H13A—C13—H13B	109.5
O3—C11—C13	106.18 (11)	C11—C13—H13C	109.5
O4—C11—C12	110.47 (11)	H13A—C13—H13C	109.5
O3—C11—C12	110.71 (11)	H13B—C13—H13C	109.5
C13—C11—C12	113.52 (12)	C1—C2—C3	119.93 (14)
C9—C7—C4	130.10 (11)	C1—C2—H2A	120.0
C9—C7—H7A	114.9	C3—C2—H2A	120.0
C4—C7—H7A	114.9	C2—C1—C6	120.39 (13)
C7—C9—C10	125.14 (11)	C2—C1—H1A	119.8
C7—C9—C8	117.26 (11)	C6—C1—H1A	119.8
C10—C9—C8	117.09 (10)	C11—C12—H12A	109.5
C5—C6—C1	118.59 (13)	C11—C12—H12B	109.5
C5—C6—H6A	120.7	H12A—C12—H12B	109.5
C1—C6—H6A	120.7	C11—C12—H12C	109.5
F—C5—C6	118.32 (12)	H12A—C12—H12C	109.5
F—C5—C4	118.57 (12)	H12B—C12—H12C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1i	0.93	2.42	3.343 (4)	174
C7—H7A···O1	0.93	2.42	2.798 (2)	104

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1i	0.93	2.42	3.343 (4)	174

Symmetry code: (i) .