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

The title compound, C(13)H(12)O(5), was prepared by the reaction of 2,2-dimethyl-1,3-dioxane-4,6-dione and 4-hy-droxy-benz-alde-hyde 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 R(2) (2)(20) rings.

Related literature

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

Experimental

Crystal data

C13H12O5

M = 248.23

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.116

S = 1.05

2644 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.28 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/S1600536810032149/hb5605sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032149/hb5605Isup2.hkl

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

C13H12O5	F(000) = 520
Mr = 248.23	Dx = 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

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

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(Fo2) + (0.0685P)2 + 0.2332P] where P = (Fo2 + 2Fc2)/3
2644 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.28 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	0.41524 (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*

	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)

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

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

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) .