(E)-2,2-Dimethyl-5-(3-phenyl-allyl-idene)-1,3-dioxane-4,6-dione.

The title compound, C(15)H(14)O(4), was prepared by the reaction of 2,2-dimethyl-1,3-dioxane-4,6-dione and (Z)-3-phenyl-acryl-aldehyde in ethanol. The dioxane ring is in a sofa conformation with the C atom bonded to the two methyl groups forming the flap. With the exception of the flap atom and the methyl group C atoms, all other non-H atoms are essentially planar, with an r.m.s. deviation of 0.067 (1) Å. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C15H14O4

M = 258.26

Triclinic,

a = 6.9171 (14) Å

b = 7.0961 (14) Å

c = 13.732 (3) Å

α = 94.79 (3)°

β = 90.79 (3)°

γ = 98.31 (3)°

V = 664.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

6475 measured reflections

3006 independent reflections

2319 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.170

S = 1.25

3006 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.30 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/S1600536810042534/lh5147sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042534/lh5147Isup2.hkl

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

C15H14O4	Z = 2
Mr = 258.26	F(000) = 272
Triclinic, P1	Dx = 1.291 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9171 (14) Å	Cell parameters from 2319 reflections
b = 7.0961 (14) Å	θ = 3.2–27.5°
c = 13.732 (3) Å	µ = 0.09 mm−1
α = 94.79 (3)°	T = 293 K
β = 90.79 (3)°	Block, yellow
γ = 98.31 (3)°	0.20 × 0.15 × 0.10 mm
V = 664.4 (2) Å3

Bruker SMART CCD area-detector diffractometer	2319 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
graphite	θmax = 27.5°, θmin = 3.2°
phi and ω scans	h = −8→8
6475 measured reflections	k = −9→9
3006 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 1.25	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
3006 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.30 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	0.11039 (12)	0.49034 (12)	0.88464 (7)	0.0556 (3)
O1	0.26632 (13)	0.73340 (13)	0.79292 (7)	0.0576 (3)
C10	0.40643 (17)	0.44465 (17)	0.80181 (9)	0.0489 (3)
C9	0.53406 (18)	0.32290 (19)	0.77683 (9)	0.0533 (3)
H9A	0.5087	0.2047	0.8024	0.064*
O4	0.52765 (15)	0.70212 (16)	0.70801 (9)	0.0790 (4)
O3	0.21672 (17)	0.21587 (14)	0.89068 (9)	0.0782 (4)
C11	0.24288 (19)	0.37290 (18)	0.86240 (9)	0.0534 (3)
C8	0.70169 (18)	0.3474 (2)	0.71739 (10)	0.0546 (3)
H8A	0.7361	0.4617	0.6891	0.066*
C12	0.41250 (18)	0.63399 (19)	0.76415 (10)	0.0537 (3)
C15	−0.0208 (2)	0.7761 (2)	0.87670 (11)	0.0621 (4)
H15A	−0.0951	0.7213	0.8191	0.093*
H15B	0.0082	0.9121	0.8745	0.093*
H15C	−0.0953	0.7481	0.9335	0.093*
C7	0.80960 (19)	0.2062 (2)	0.70229 (9)	0.0569 (3)
H7A	0.7673	0.0944	0.7315	0.068*
C5	0.98573 (19)	0.2077 (2)	0.64538 (9)	0.0553 (3)
C13	0.16573 (17)	0.69346 (17)	0.88135 (9)	0.0503 (3)
C4	1.06834 (19)	0.3651 (2)	0.59900 (11)	0.0648 (4)
H4A	1.0124	0.4769	0.6049	0.078*
C6	1.0760 (2)	0.0447 (2)	0.63695 (11)	0.0726 (4)
H6A	1.0236	−0.0620	0.6680	0.087*
C14	0.2935 (2)	0.7718 (2)	0.96872 (12)	0.0717 (4)
H14A	0.4106	0.7137	0.9673	0.108*
H14B	0.2248	0.7443	1.0273	0.108*
H14C	0.3271	0.9077	0.9675	0.108*
C3	1.2336 (2)	0.3567 (3)	0.54389 (13)	0.0784 (5)
H3A	1.2869	0.4624	0.5123	0.094*
C2	1.3187 (2)	0.1942 (3)	0.53569 (14)	0.0887 (6)
H2A	1.4286	0.1886	0.4979	0.106*
C1	1.2416 (3)	0.0393 (3)	0.58337 (14)	0.0903 (6)
H1A	1.3018	−0.0700	0.5794	0.108*

	U11	U22	U33	U12	U13	U23
O2	0.0584 (5)	0.0430 (5)	0.0644 (6)	0.0006 (4)	0.0176 (4)	0.0074 (4)
O1	0.0619 (5)	0.0547 (5)	0.0613 (6)	0.0155 (4)	0.0176 (4)	0.0212 (4)
C10	0.0530 (6)	0.0473 (7)	0.0473 (6)	0.0056 (5)	0.0066 (5)	0.0115 (5)
C9	0.0593 (7)	0.0520 (7)	0.0500 (7)	0.0098 (5)	0.0023 (5)	0.0097 (5)
O4	0.0782 (7)	0.0716 (7)	0.0972 (8)	0.0208 (5)	0.0424 (6)	0.0429 (6)
O3	0.1022 (8)	0.0478 (6)	0.0891 (8)	0.0118 (5)	0.0430 (6)	0.0245 (5)
C11	0.0652 (7)	0.0439 (7)	0.0509 (7)	0.0035 (5)	0.0112 (6)	0.0082 (5)
C8	0.0546 (7)	0.0582 (7)	0.0525 (7)	0.0106 (5)	0.0027 (5)	0.0086 (5)
C12	0.0531 (6)	0.0531 (7)	0.0577 (7)	0.0087 (5)	0.0127 (5)	0.0180 (6)
C15	0.0607 (7)	0.0590 (8)	0.0679 (9)	0.0116 (6)	0.0127 (6)	0.0063 (6)
C7	0.0603 (7)	0.0609 (8)	0.0519 (7)	0.0148 (6)	0.0021 (6)	0.0098 (6)
C5	0.0556 (7)	0.0672 (8)	0.0463 (7)	0.0197 (6)	−0.0027 (5)	0.0050 (6)
C13	0.0567 (6)	0.0423 (6)	0.0510 (7)	0.0014 (5)	0.0104 (5)	0.0081 (5)
C4	0.0582 (7)	0.0763 (10)	0.0642 (8)	0.0191 (7)	0.0015 (6)	0.0144 (7)
C6	0.0820 (9)	0.0768 (10)	0.0665 (9)	0.0339 (8)	0.0090 (8)	0.0096 (8)
C14	0.0797 (9)	0.0637 (9)	0.0678 (9)	0.0026 (7)	−0.0088 (7)	−0.0016 (7)
C3	0.0592 (8)	0.1082 (14)	0.0715 (10)	0.0144 (8)	0.0096 (7)	0.0236 (9)
C2	0.0677 (9)	0.1327 (18)	0.0731 (10)	0.0386 (10)	0.0170 (8)	0.0082 (11)
C1	0.0914 (12)	0.1067 (14)	0.0844 (12)	0.0537 (11)	0.0177 (10)	0.0057 (10)

O2—C11	1.3468 (15)	C7—C5	1.456 (2)
O2—C13	1.4415 (14)	C7—H7A	0.9300
O1—C12	1.3590 (15)	C5—C4	1.387 (2)
O1—C13	1.4362 (15)	C5—C6	1.389 (2)
C10—C9	1.3501 (17)	C13—C14	1.4992 (19)
C10—C11	1.4702 (18)	C4—C3	1.385 (2)
C10—C12	1.4746 (17)	C4—H4A	0.9300
C9—C8	1.4256 (19)	C6—C1	1.374 (2)
C9—H9A	0.9300	C6—H6A	0.9300
O4—C12	1.1959 (16)	C14—H14A	0.9600
O3—C11	1.2004 (15)	C14—H14B	0.9600
C8—C7	1.3375 (18)	C14—H14C	0.9600
C8—H8A	0.9300	C3—C2	1.366 (2)
C15—C13	1.4955 (17)	C3—H3A	0.9300
C15—H15A	0.9600	C2—C1	1.372 (3)
C15—H15B	0.9600	C2—H2A	0.9300
C15—H15C	0.9600	C1—H1A	0.9300
C11—O2—C13	119.15 (10)	C6—C5—C7	118.85 (14)
C12—O1—C13	119.85 (9)	O1—C13—O2	110.44 (10)
C9—C10—C11	116.66 (11)	O1—C13—C15	106.78 (10)
C9—C10—C12	123.71 (12)	O2—C13—C15	106.17 (10)
C11—C10—C12	119.36 (11)	O1—C13—C14	110.25 (11)
C10—C9—C8	130.02 (12)	O2—C13—C14	109.54 (10)
C10—C9—H9A	115.0	C15—C13—C14	113.55 (13)
C8—C9—H9A	115.0	C3—C4—C5	120.42 (15)
O3—C11—O2	118.16 (12)	C3—C4—H4A	119.8
O3—C11—C10	124.58 (13)	C5—C4—H4A	119.8
O2—C11—C10	117.22 (10)	C1—C6—C5	120.81 (17)
C7—C8—C9	120.10 (13)	C1—C6—H6A	119.6
C7—C8—H8A	119.9	C5—C6—H6A	119.6
C9—C8—H8A	119.9	C13—C14—H14A	109.5
O4—C12—O1	118.08 (11)	C13—C14—H14B	109.5
O4—C12—C10	126.04 (12)	H14A—C14—H14B	109.5
O1—C12—C10	115.79 (11)	C13—C14—H14C	109.5
C13—C15—H15A	109.5	H14A—C14—H14C	109.5
C13—C15—H15B	109.5	H14B—C14—H14C	109.5
H15A—C15—H15B	109.5	C2—C3—C4	120.37 (17)
C13—C15—H15C	109.5	C2—C3—H3A	119.8
H15A—C15—H15C	109.5	C4—C3—H3A	119.8
H15B—C15—H15C	109.5	C3—C2—C1	119.80 (16)
C8—C7—C5	127.42 (13)	C3—C2—H2A	120.1
C8—C7—H7A	116.3	C1—C2—H2A	120.1
C5—C7—H7A	116.3	C2—C1—C6	120.36 (16)
C4—C5—C6	118.21 (13)	C2—C1—H1A	119.8
C4—C5—C7	122.93 (13)	C6—C1—H1A	119.8

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15B···O3i	0.96	2.41	3.2991 (19)	155
C15—H15C···O3ii	0.96	2.57	3.486 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯O3i	0.96	2.41	3.2991 (19)	155
C15—H15C⋯O3ii	0.96	2.57	3.486 (2)	159

Symmetry codes: (i) ; (ii) .