5-(4-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 4-fluoro-benz-alde-hyde in ethanol. The 1,3-dioxane ring adopts an envelope conformation. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For background information on the use of Meldrum’s acid (2,2-dimethyl-1,3-dioxane-4,6-dione) in organic synthesis, see: Kuhn et al. (2003 ▶); Casadesus et al. (2006 ▶). For a related structure, see: Zeng & Jian (2009 ▶).

Experimental

Crystal data

C13H11FO4

M = 250.22

Monoclinic,

a = 10.607 (2) Å

b = 10.413 (2) Å

c = 11.366 (2) Å

β = 106.09 (3)°

V = 1206.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.17 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

11341 measured reflections

2748 independent reflections

1773 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.182

S = 1.16

2748 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.24 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/S1600536810033155/lh5116sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033155/lh5116Isup2.hkl

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

C13H11FO4	F(000) = 520
Mr = 250.22	Dx = 1.378 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2748 reflections
a = 10.607 (2) Å	θ = 3.0–27.5°
b = 10.413 (2) Å	µ = 0.11 mm−1
c = 11.366 (2) Å	T = 293 K
β = 106.09 (3)°	Block, colorless
V = 1206.2 (4) Å3	0.17 × 0.15 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	1773 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
graphite	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −13→13
11341 measured reflections	k = −13→13
2748 independent reflections	l = −14→13

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2748 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.24 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
O2	0.19531 (11)	0.04581 (14)	0.03108 (11)	0.0683 (4)
O4	0.48662 (11)	0.09217 (13)	−0.12156 (11)	0.0669 (4)
O1	0.29516 (11)	0.01292 (14)	−0.12672 (11)	0.0685 (4)
C7	0.46120 (16)	0.27281 (18)	0.07462 (14)	0.0588 (4)
H7A	0.4452	0.3029	0.1462	0.071*
O3	0.27783 (14)	0.17669 (16)	0.18433 (12)	0.0848 (5)
C5	0.38086 (15)	0.17577 (16)	0.02221 (13)	0.0541 (4)
C4	0.39340 (15)	0.09646 (17)	−0.08040 (15)	0.0566 (4)
C8	0.56723 (16)	0.34028 (17)	0.04331 (14)	0.0577 (4)
C6	0.28220 (17)	0.13664 (19)	0.08633 (16)	0.0625 (5)
C3	0.17201 (16)	0.0255 (2)	−0.09776 (16)	0.0661 (5)
C13	0.65632 (18)	0.4046 (2)	0.13807 (17)	0.0693 (5)
H13A	0.6460	0.4008	0.2166	0.083*
C9	0.5822 (2)	0.3527 (2)	−0.07392 (17)	0.0706 (5)
H9A	0.5226	0.3128	−0.1394	0.085*
F1	0.86826 (14)	0.55357 (17)	−0.01890 (16)	0.1227 (6)
C10	0.6833 (2)	0.4228 (2)	−0.0945 (2)	0.0837 (6)
H10A	0.6928	0.4306	−0.1731	0.100*
C2	0.0951 (2)	0.1370 (2)	−0.16850 (19)	0.0837 (6)
H2A	0.1444	0.2149	−0.1462	0.126*
H2B	0.0128	0.1447	−0.1494	0.126*
H2C	0.0794	0.1222	−0.2547	0.126*
C12	0.75946 (19)	0.4739 (2)	0.1185 (2)	0.0806 (6)
H12A	0.8200	0.5144	0.1828	0.097*
C11	0.7695 (2)	0.4809 (2)	0.0023 (2)	0.0814 (6)
C1	0.1052 (2)	−0.1014 (2)	−0.1254 (2)	0.0918 (7)
H1A	0.1597	−0.1669	−0.0775	0.138*
H1B	0.0900	−0.1205	−0.2109	0.138*
H1C	0.0229	−0.0986	−0.1058	0.138*

	U11	U22	U33	U12	U13	U23
O2	0.0660 (7)	0.0800 (9)	0.0650 (8)	−0.0019 (6)	0.0283 (6)	0.0010 (6)
O4	0.0655 (7)	0.0787 (9)	0.0648 (8)	0.0073 (6)	0.0321 (6)	−0.0021 (6)
O1	0.0620 (7)	0.0813 (9)	0.0663 (8)	−0.0011 (6)	0.0244 (6)	−0.0140 (6)
C7	0.0654 (9)	0.0671 (11)	0.0449 (8)	0.0118 (8)	0.0173 (7)	0.0042 (7)
O3	0.0943 (10)	0.1107 (13)	0.0621 (8)	−0.0072 (8)	0.0427 (7)	−0.0087 (7)
C5	0.0562 (8)	0.0627 (10)	0.0464 (8)	0.0083 (7)	0.0192 (6)	0.0048 (7)
C4	0.0580 (9)	0.0631 (10)	0.0500 (8)	0.0089 (7)	0.0169 (7)	0.0027 (7)
C8	0.0615 (9)	0.0602 (10)	0.0516 (9)	0.0086 (7)	0.0162 (7)	0.0035 (7)
C6	0.0659 (10)	0.0709 (12)	0.0552 (10)	0.0076 (8)	0.0244 (8)	0.0058 (8)
C3	0.0568 (9)	0.0811 (13)	0.0635 (10)	0.0024 (8)	0.0219 (8)	−0.0051 (9)
C13	0.0696 (11)	0.0759 (13)	0.0609 (10)	0.0036 (9)	0.0157 (8)	−0.0028 (9)
C9	0.0817 (12)	0.0749 (13)	0.0558 (10)	−0.0003 (10)	0.0199 (9)	0.0067 (8)
F1	0.0936 (9)	0.1271 (13)	0.1624 (16)	−0.0198 (9)	0.0608 (10)	0.0147 (10)
C10	0.0994 (15)	0.0889 (16)	0.0738 (13)	0.0043 (12)	0.0424 (12)	0.0138 (11)
C2	0.0683 (11)	0.0995 (16)	0.0783 (13)	0.0120 (11)	0.0121 (10)	0.0050 (12)
C12	0.0655 (11)	0.0870 (15)	0.0845 (14)	−0.0003 (10)	0.0130 (10)	−0.0014 (11)
C11	0.0621 (10)	0.0815 (14)	0.1091 (16)	0.0033 (10)	0.0377 (11)	0.0108 (13)
C1	0.0819 (13)	0.0876 (16)	0.1103 (18)	−0.0143 (11)	0.0337 (12)	−0.0196 (13)

O2—C6	1.348 (2)	C13—C12	1.379 (3)
O2—C3	1.432 (2)	C13—H13A	0.9300
O4—C4	1.2063 (19)	C9—C10	1.370 (3)
O1—C4	1.347 (2)	C9—H9A	0.9300
O1—C3	1.4388 (19)	F1—C11	1.367 (2)
C7—C5	1.349 (2)	C10—C11	1.362 (3)
C7—C8	1.451 (2)	C10—H10A	0.9300
C7—H7A	0.9300	C2—H2A	0.9600
O3—C6	1.202 (2)	C2—H2B	0.9600
C5—C4	1.465 (2)	C2—H2C	0.9600
C5—C6	1.488 (2)	C12—C11	1.356 (3)
C8—C9	1.391 (2)	C12—H12A	0.9300
C8—C13	1.392 (3)	C1—H1A	0.9600
C3—C1	1.491 (3)	C1—H1B	0.9600
C3—C2	1.516 (3)	C1—H1C	0.9600
C6—O2—C3	118.82 (14)	C8—C13—H13A	119.1
C4—O1—C3	120.31 (14)	C10—C9—C8	121.03 (19)
C5—C7—C8	133.77 (16)	C10—C9—H9A	119.5
C5—C7—H7A	113.1	C8—C9—H9A	119.5
C8—C7—H7A	113.1	C11—C10—C9	118.7 (2)
C7—C5—C4	126.02 (15)	C11—C10—H10A	120.6
C7—C5—C6	115.63 (15)	C9—C10—H10A	120.6
C4—C5—C6	117.82 (15)	C3—C2—H2A	109.5
O4—C4—O1	116.92 (15)	C3—C2—H2B	109.5
O4—C4—C5	126.49 (16)	H2A—C2—H2B	109.5
O1—C4—C5	116.36 (14)	C3—C2—H2C	109.5
C9—C8—C13	117.60 (18)	H2A—C2—H2C	109.5
C9—C8—C7	125.56 (16)	H2B—C2—H2C	109.5
C13—C8—C7	116.70 (15)	C11—C12—C13	117.8 (2)
O3—C6—O2	118.56 (17)	C11—C12—H12A	121.1
O3—C6—C5	124.86 (18)	C13—C12—H12A	121.1
O2—C6—C5	116.53 (15)	C12—C11—C10	123.1 (2)
O2—C3—O1	109.70 (13)	C12—C11—F1	118.2 (2)
O2—C3—C1	106.49 (17)	C10—C11—F1	118.6 (2)
O1—C3—C1	106.23 (16)	C3—C1—H1A	109.5
O2—C3—C2	110.14 (16)	C3—C1—H1B	109.5
O1—C3—C2	109.73 (16)	H1A—C1—H1B	109.5
C1—C3—C2	114.39 (16)	C3—C1—H1C	109.5
C12—C13—C8	121.71 (19)	H1A—C1—H1C	109.5
C12—C13—H13A	119.1	H1B—C1—H1C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1i	0.93	2.47	3.373 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O1i	0.93	2.47	3.373 (3)	164

Symmetry code: (i) .