5-(4-Hy­droxy­benzyl­idene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Zeng, W.-L.

doi:10.1107/S1600536810032149

organic compounds

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https://doi.org/10.1107/S1600536810032149

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5-(4-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Wu-Lan Zeng ^a ^*

^aMicroScale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: wulanzeng@163.com

(Received 8 August 2010; accepted 10 August 2010; online 18 August 2010)

The title compound, C₁₃H₁₂O₅, was prepared by the reaction of 2,2-dimethyl-1,3-dioxane-4,6-dione and 4-hydroxybenzaldehyde in ethanol. The 1,3-dioxane ring is in a distorted boat conformation. In the crystal, inversion dimers linked by pairs of O—H⋯O hydrogen bonds generate R₂²(20) rings.

Related literature

For a related structure, see: Zeng & Jian (2009 ).

Experimental

Crystal data

C₁₃H₁₂O₅
M_r = 248.23
Monoclinic, P 2₁ /c
a = 13.900 (3) Å
b = 10.249 (2) Å
c = 8.1357 (16) Å
β = 94.47 (3)°
V = 1155.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.20 × 0.16 × 0.11 mm

Data collection

Bruker SMART CCD diffractometer
10923 measured reflections
2644 independent reflections
2402 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.116
S = 1.05
2644 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O2ⁱ	0.82	1.98	2.7919 (14)	170
Symmetry code: (i) -x, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810032149/hb5605sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032149/hb5605Isup2.hkl

checkCIF report

Comment top

We have recently reported the crystal structure of 5-(2-fluorobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (Zeng & Jian 2009). As part of our search for new Meldrum's acid derivatives, the title compound, (I) (Fig. 1), has been synthesized and its structure is reported here. The crystal structure analysis confirms the title compound with atom C7 bridged by the 1,3-dioxane ring via C7═C6 double bond [1.3580 (16)Å] and the phenyl ring via C7-C8 single bond [1.4513 (15)Å], forming the C6-C7-C8 bond angle of 134.33 (10)°. The crystal structure is stabilized by weak intermolecular O—H···O hydrogen bonds (Table 1).

Related literature top

For a related structure, see: Zeng & Jian (2009).

Experimental top

A mixture of malonic acid (6.24 g, 0.06 mol) and acetic anhydride (9 ml) in strong sulfuric acid (0.25 ml) was stirred with water at 303 K, After dissolving, propan-2-one (3.48 g, 0.06 mol) was added dropwise into solution for 1 h. The reaction was allowed to proceed for 2 h. The mixture was cooled and filtered, and then an ethanol solution of 4-hydroxybenzaldehyde (7.32g, 0.06 mol) was added. The solution was then filtered and concentrated. Yellow blocks of (I) were obtained by evaporation of an petroleum ether-acetone (2:1 v/v) solution of the title compound at room temperature over a period of several days.

Structure description top

For a related structure, see: Zeng & Jian (2009).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids and spheres of arbritrary size for the H atoms.

5-(4-Hydroxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione top

Crystal data top

C₁₃H₁₂O₅	F(000) = 520
M_r = 248.23	D_x = 1.427 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2644 reflections
a = 13.900 (3) Å	θ = 3.2–27.5°
b = 10.249 (2) Å	µ = 0.11 mm⁻¹
c = 8.1357 (16) Å	T = 293 K
β = 94.47 (3)°	Block, yellow
V = 1155.5 (4) Å³	0.20 × 0.16 × 0.11 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2402 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
phi and ω scans	h = −17→18
10923 measured reflections	k = −13→13
2644 independent reflections	l = −10→10

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0685P)² + 0.2332P] where P = (F_o² + 2F_c²)/3
2644 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₃H₁₂O₅	V = 1155.5 (4) Å³
M_r = 248.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.900 (3) Å	µ = 0.11 mm⁻¹
b = 10.249 (2) Å	T = 293 K
c = 8.1357 (16) Å	0.20 × 0.16 × 0.11 mm
β = 94.47 (3)°

Data collection top

Bruker SMART CCD diffractometer	2402 reflections with I > 2σ(I)
10923 measured reflections	R_int = 0.035
2644 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.05	Δρ_max = 0.25 e Å⁻³
2644 reflections	Δρ_min = −0.28 e Å⁻³
163 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O4	0.41524 (6)	0.57554 (9)	0.12495 (11)	0.0401 (2)
O3	0.35540 (6)	0.47383 (10)	0.35423 (10)	0.0409 (2)
O2	0.21646 (6)	0.52747 (11)	0.44151 (11)	0.0468 (3)
O5	−0.22815 (6)	0.59477 (10)	0.25091 (12)	0.0468 (3)
H5A	−0.2323	0.5600	0.3408	0.070*
C7	0.15802 (8)	0.63304 (11)	0.10210 (14)	0.0317 (2)
H7A	0.1617	0.6830	0.0074	0.038*
C11	−0.13455 (8)	0.59747 (11)	0.21578 (14)	0.0316 (2)
C8	0.05963 (8)	0.61437 (10)	0.14540 (13)	0.0288 (2)
C13	0.02894 (8)	0.52087 (11)	0.25578 (14)	0.0313 (2)
H13A	0.0739	0.4638	0.3070	0.038*
C12	−0.06604 (8)	0.51181 (11)	0.28980 (14)	0.0320 (3)
H12A	−0.0848	0.4483	0.3625	0.038*
O1	0.32758 (7)	0.71114 (11)	−0.03290 (14)	0.0580 (3)
C5	0.26819 (8)	0.52924 (12)	0.32898 (14)	0.0337 (3)
C6	0.24587 (8)	0.59391 (11)	0.16895 (14)	0.0318 (2)
C9	−0.01161 (8)	0.69363 (11)	0.06446 (14)	0.0337 (3)
H9A	0.0060	0.7520	−0.0155	0.040*
C10	−0.10703 (8)	0.68732 (11)	0.10023 (15)	0.0355 (3)
H10A	−0.1525	0.7428	0.0474	0.043*
C4	0.32958 (9)	0.63232 (12)	0.07624 (15)	0.0373 (3)
C3	0.41508 (8)	0.45675 (13)	0.21746 (14)	0.0366 (3)
C2	0.51631 (10)	0.43795 (19)	0.29247 (18)	0.0544 (4)
H2A	0.5351	0.5122	0.3594	0.082*
H2B	0.5593	0.4289	0.2064	0.082*
H2C	0.5192	0.3608	0.3595	0.082*
C1	0.37811 (12)	0.34509 (14)	0.11015 (19)	0.0525 (4)
H1A	0.3133	0.3633	0.0669	0.079*
H1B	0.3789	0.2665	0.1744	0.079*
H1C	0.4186	0.3343	0.0207	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0294 (4)	0.0477 (5)	0.0443 (5)	−0.0016 (3)	0.0091 (3)	0.0076 (4)
O3	0.0317 (4)	0.0625 (6)	0.0287 (4)	0.0045 (4)	0.0036 (3)	0.0062 (4)
O2	0.0318 (4)	0.0783 (7)	0.0309 (4)	−0.0035 (4)	0.0067 (3)	0.0073 (4)
O5	0.0273 (4)	0.0666 (6)	0.0468 (5)	0.0088 (4)	0.0051 (4)	0.0100 (5)
C7	0.0339 (6)	0.0314 (5)	0.0302 (5)	−0.0014 (4)	0.0052 (4)	0.0013 (4)
C11	0.0270 (5)	0.0372 (6)	0.0303 (5)	0.0024 (4)	0.0003 (4)	−0.0045 (4)
C8	0.0290 (5)	0.0293 (5)	0.0281 (5)	−0.0001 (4)	0.0015 (4)	−0.0026 (4)
C13	0.0286 (5)	0.0316 (5)	0.0334 (5)	0.0038 (4)	0.0007 (4)	0.0037 (4)
C12	0.0310 (5)	0.0352 (5)	0.0299 (5)	0.0005 (4)	0.0026 (4)	0.0039 (4)
O1	0.0496 (6)	0.0612 (6)	0.0660 (7)	0.0073 (5)	0.0224 (5)	0.0309 (5)
C5	0.0273 (5)	0.0443 (6)	0.0294 (5)	−0.0052 (4)	0.0025 (4)	0.0005 (4)
C6	0.0298 (5)	0.0360 (5)	0.0301 (5)	−0.0023 (4)	0.0063 (4)	0.0010 (4)
C9	0.0365 (6)	0.0311 (5)	0.0327 (5)	−0.0015 (4)	−0.0015 (4)	0.0038 (4)
C10	0.0334 (6)	0.0347 (6)	0.0373 (6)	0.0052 (4)	−0.0047 (4)	0.0032 (5)
C4	0.0332 (6)	0.0393 (6)	0.0406 (6)	−0.0009 (4)	0.0100 (5)	0.0050 (5)
C3	0.0326 (6)	0.0481 (7)	0.0297 (5)	0.0031 (5)	0.0051 (4)	0.0032 (5)
C2	0.0337 (6)	0.0894 (11)	0.0402 (7)	0.0138 (7)	0.0031 (5)	0.0039 (7)
C1	0.0594 (9)	0.0470 (8)	0.0511 (8)	−0.0002 (6)	0.0036 (7)	−0.0049 (6)

Geometric parameters (Å, º) top

O4—C4	1.3564 (15)	C12—H12A	0.9300
O4—C3	1.4314 (15)	O1—C4	1.1991 (15)
O3—C5	1.3399 (15)	C5—C6	1.4722 (16)
O3—C3	1.4493 (14)	C6—C4	1.4882 (16)
O2—C5	1.2076 (15)	C9—C10	1.3814 (17)
O5—C11	1.3539 (14)	C9—H9A	0.9300
O5—H5A	0.8200	C10—H10A	0.9300
C7—C6	1.3580 (16)	C3—C2	1.5019 (17)
C7—C8	1.4513 (15)	C3—C1	1.5053 (19)
C7—H7A	0.9300	C2—H2A	0.9600
C11—C10	1.3907 (17)	C2—H2B	0.9600
C11—C12	1.3968 (16)	C2—H2C	0.9600
C8—C13	1.4023 (15)	C1—H1A	0.9600
C8—C9	1.4044 (15)	C1—H1B	0.9600
C13—C12	1.3730 (16)	C1—H1C	0.9600
C13—H13A	0.9300

C4—O4—C3	118.76 (9)	C8—C9—H9A	119.1
C5—O3—C3	119.91 (9)	C9—C10—C11	119.52 (10)
C11—O5—H5A	109.5	C9—C10—H10A	120.2
C6—C7—C8	134.33 (10)	C11—C10—H10A	120.2
C6—C7—H7A	112.8	O1—C4—O4	118.33 (11)
C8—C7—H7A	112.8	O1—C4—C6	125.42 (12)
O5—C11—C10	118.41 (10)	O4—C4—C6	116.21 (10)
O5—C11—C12	122.02 (11)	O4—C3—O3	108.99 (10)
C10—C11—C12	119.56 (10)	O4—C3—C2	106.43 (11)
C13—C8—C9	117.19 (10)	O3—C3—C2	106.12 (10)
C13—C8—C7	125.81 (10)	O4—C3—C1	110.86 (10)
C9—C8—C7	116.95 (10)	O3—C3—C1	110.31 (11)
C12—C13—C8	121.38 (10)	C2—C3—C1	113.88 (13)
C12—C13—H13A	119.3	C3—C2—H2A	109.5
C8—C13—H13A	119.3	C3—C2—H2B	109.5
C13—C12—C11	120.30 (10)	H2A—C2—H2B	109.5
C13—C12—H12A	119.9	C3—C2—H2C	109.5
C11—C12—H12A	119.9	H2A—C2—H2C	109.5
O2—C5—O3	117.55 (11)	H2B—C2—H2C	109.5
O2—C5—C6	125.47 (11)	C3—C1—H1A	109.5
O3—C5—C6	116.88 (10)	C3—C1—H1B	109.5
C7—C6—C5	127.45 (10)	H1A—C1—H1B	109.5
C7—C6—C4	115.66 (10)	C3—C1—H1C	109.5
C5—C6—C4	116.62 (10)	H1A—C1—H1C	109.5
C10—C9—C8	121.84 (10)	H1B—C1—H1C	109.5
C10—C9—H9A	119.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2ⁱ	0.82	1.98	2.7919 (14)	170

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂O₅
M_r	248.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.900 (3), 10.249 (2), 8.1357 (16)
β (°)	94.47 (3)
V (Å³)	1155.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.16 × 0.11

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10923, 2644, 2402
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.116, 1.05
No. of reflections	2644
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.28

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2ⁱ	0.82	1.98	2.7919 (14)	170

Symmetry code: (i) −x, −y+1, −z+1.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zeng, W.-L. & Jian, F.-F. (2009). Acta Cryst. E65, o2587. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2319

https://doi.org/10.1107/S1600536810032149

Open

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