4a-Hydroxy-9-(4-hydroxyphenyl)-4,4a,5,6,9,9a-hexahydro-3H-xanthene-1,8(2H,7H)-dione.

The title compound, C(19)H(20)O(5), was synthesized by the reaction of 1,3-cyclo-hexa-nedione and 4-hy-droxy-benzaldehyde in the presence of PdCl(2) and thio-urea. The tetra-hydro-pyran ring and the six-membered cyclo-hexene ring adopt envelope conformations, and the six-membered cyclo-hexane ring is in a chair conformation. The crystal packing is stabilized by classical inter-molecular O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions.

Related literature

For applications of related compounds, see: Menchen et al. (2003 ▶); Saint-Ruf et al. (1972 ▶); Reddy et al. (2009 ▶); Mehdi et al. (2011 ▶). For the synthesis of related compounds, see: Karade et al. (2007 ▶); Luna et al. (2009 ▶). For related structures, see: Loh et al. (2011 ▶); Yang et al. (2011 ▶).

Experimental

Crystal data

C19H20O5

M = 328.35

Monoclinic,

a = 9.014 (4) Å

b = 10.242 (4) Å

c = 9.289 (4) Å

β = 108.194 (4)°

V = 814.7 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.35 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.967, T max = 0.981

4840 measured reflections

1876 independent reflections

1652 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.113

S = 1.04

1863 reflections

219 parameters

14 restraints

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811038335/rk2296sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038335/rk2296Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811038335/rk2296Isup3.cml

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

C19H20O5	F(000) = 348.0
Mr = 328.35	Dx = 1.339 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1885 reflections
a = 9.014 (4) Å	θ = 2.4–26.8°
b = 10.242 (4) Å	µ = 0.10 mm−1
c = 9.289 (4) Å	T = 295 K
β = 108.194 (4)°	Block, colourless
V = 814.7 (6) Å3	0.35 × 0.30 × 0.20 mm
Z = 2

Bruker APEXII CCD diffractometer	1876 independent reflections
Radiation source: fine-focus sealed tube	1652 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ– and ω–scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
Tmin = 0.967, Tmax = 0.981	k = −13→12
4840 measured reflections	l = −10→11

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0658P)2 + 0.1291P] where P = (Fo2 + 2Fc2)/3
1863 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 0.41 e Å−3
14 restraints	Δρmin = −0.19 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C9	0.1903 (3)	0.1561 (2)	0.8768 (3)	0.0289 (5)
H9	0.1954	0.0612	0.8912	0.035*
C9A	0.3440 (3)	0.2024 (3)	0.8614 (3)	0.0307 (5)
C4A	0.4337 (3)	0.2922 (3)	0.9542 (3)	0.0354 (6)
C8A	0.1606 (3)	0.2192 (3)	1.0149 (3)	0.0307 (6)
H13	0.1037	0.3003	0.9782	0.037*
C5	0.2735 (3)	0.3317 (3)	1.2653 (3)	0.0407 (7)
H5A	0.2174	0.4116	1.2264	0.049*
H5B	0.3707	0.3551	1.3417	0.049*
C8	0.0566 (3)	0.1394 (3)	1.0823 (3)	0.0432 (7)
C6	0.1760 (4)	0.2471 (4)	1.3358 (4)	0.0483 (8)
H6A	0.1504	0.2962	1.4142	0.058*
H6B	0.2362	0.1712	1.3826	0.058*
C1	0.4046 (3)	0.1347 (3)	0.7535 (3)	0.0375 (6)
C4B	0.3076 (3)	0.2586 (3)	1.1383 (3)	0.0338 (6)
C4	0.5792 (4)	0.3490 (4)	0.9360 (4)	0.0492 (8)
H4A	0.6694	0.3118	1.0114	0.059*
H4B	0.5803	0.4426	0.9525	0.059*
C7	0.0251 (4)	0.2026 (4)	1.2164 (4)	0.0540 (9)
H7A	−0.0287	0.1409	1.2619	0.065*
H7B	−0.0428	0.2774	1.1820	0.065*
C2	0.5553 (4)	0.1824 (4)	0.7353 (5)	0.0656 (11)
H2A	0.6403	0.1290	0.7971	0.079*
H2B	0.5513	0.1715	0.6304	0.079*
C3	0.5892 (6)	0.3217 (5)	0.7787 (6)	0.0818 (15)
H3A	0.5151	0.3768	0.7058	0.098*
H3B	0.6930	0.3433	0.7760	0.098*
O1	0.4005 (2)	0.34289 (19)	1.0760 (2)	0.0357 (4)
O2	0.3391 (3)	0.0380 (2)	0.6848 (3)	0.0487 (6)
O4	0.3938 (2)	0.1433 (2)	1.1914 (2)	0.0435 (5)
H4	0.4795	0.1624	1.2506	0.065*
O5	−0.3220 (3)	0.2708 (3)	0.3538 (3)	0.0548 (6)
H5	−0.3326	0.3497	0.3398	0.082*
O3	0.0004 (4)	0.0370 (3)	1.0282 (3)	0.0698 (8)
C13	−0.1962 (3)	0.2473 (3)	0.4795 (3)	0.0340 (6)
C11	0.0184 (3)	0.3158 (3)	0.6905 (3)	0.0350 (6)
H19	0.0782	0.3830	0.7472	0.042*
C10	0.0564 (3)	0.1873 (3)	0.7339 (3)	0.0275 (5)
C14	−0.1588 (3)	0.1177 (3)	0.5195 (3)	0.0376 (6)
H16	−0.2179	0.0507	0.4616	0.045*
C15	−0.0334 (3)	0.0891 (3)	0.6455 (3)	0.0323 (6)
H15	−0.0086	0.0024	0.6717	0.039*
C12	−0.1073 (3)	0.3459 (3)	0.5641 (3)	0.0365 (6)
H18	−0.1312	0.4325	0.5367	0.044*

	U11	U22	U33	U12	U13	U23
C9	0.0264 (11)	0.0269 (13)	0.0275 (13)	−0.0013 (10)	0.0000 (10)	0.0017 (10)
C9A	0.0270 (11)	0.0307 (13)	0.0306 (13)	0.0014 (10)	0.0034 (10)	0.0007 (11)
C4A	0.0330 (12)	0.0342 (14)	0.0358 (14)	−0.0032 (11)	0.0062 (11)	−0.0044 (12)
C8A	0.0306 (12)	0.0304 (14)	0.0278 (13)	−0.0016 (10)	0.0045 (10)	0.0013 (11)
C5	0.0407 (14)	0.0428 (17)	0.0348 (14)	0.0025 (13)	0.0064 (11)	−0.0078 (13)
C8	0.0421 (14)	0.0477 (17)	0.0379 (15)	−0.0097 (14)	0.0099 (12)	0.0021 (14)
C6	0.0621 (19)	0.0514 (19)	0.0340 (15)	0.0075 (16)	0.0186 (14)	0.0012 (14)
C1	0.0362 (13)	0.0389 (15)	0.0330 (14)	0.0042 (12)	0.0044 (11)	−0.0019 (12)
C4B	0.0330 (13)	0.0341 (14)	0.0301 (14)	−0.0014 (11)	0.0038 (11)	−0.0037 (11)
C4	0.0409 (15)	0.0504 (18)	0.0570 (19)	−0.0156 (14)	0.0165 (14)	−0.0104 (16)
C7	0.0548 (19)	0.061 (2)	0.053 (2)	−0.0116 (17)	0.0268 (16)	−0.0054 (18)
C2	0.0526 (19)	0.079 (3)	0.075 (3)	−0.0129 (19)	0.0353 (19)	−0.029 (2)
C3	0.089 (3)	0.077 (3)	0.105 (3)	−0.036 (3)	0.066 (3)	−0.027 (3)
O1	0.0346 (9)	0.0329 (10)	0.0368 (10)	−0.0065 (8)	0.0074 (8)	−0.0081 (8)
O2	0.0484 (12)	0.0473 (13)	0.0444 (13)	0.0007 (10)	0.0059 (10)	−0.0167 (10)
O4	0.0444 (11)	0.0390 (11)	0.0378 (11)	0.0083 (9)	−0.0005 (8)	0.0008 (9)
O5	0.0443 (11)	0.0498 (14)	0.0473 (13)	0.0012 (10)	−0.0190 (9)	0.0032 (11)
O3	0.0865 (18)	0.0670 (18)	0.0645 (18)	−0.0429 (15)	0.0359 (15)	−0.0146 (14)
C13	0.0264 (12)	0.0407 (15)	0.0285 (13)	0.0015 (11)	−0.0008 (10)	0.0030 (11)
C11	0.0354 (13)	0.0309 (14)	0.0306 (13)	−0.0029 (11)	−0.0014 (10)	0.0005 (11)
C10	0.0235 (11)	0.0307 (13)	0.0250 (12)	−0.0002 (10)	0.0031 (9)	0.0025 (10)
C14	0.0300 (12)	0.0396 (16)	0.0351 (14)	−0.0079 (11)	−0.0017 (11)	−0.0065 (12)
C15	0.0319 (12)	0.0268 (13)	0.0345 (14)	−0.0013 (10)	0.0050 (11)	0.0004 (11)
C12	0.0384 (13)	0.0300 (14)	0.0344 (14)	0.0038 (11)	0.0017 (11)	0.0051 (11)

C9—C9A	1.513 (3)	C4—C3	1.518 (6)
C9—C10	1.523 (3)	C4—H4A	0.9700
C9—C8A	1.533 (4)	C4—H4B	0.9700
C9—H9	0.9800	C7—H7A	0.9700
C9A—C4A	1.345 (4)	C7—H7B	0.9700
C9A—C1	1.458 (4)	C2—C3	1.487 (6)
C4A—O1	1.360 (3)	C2—H2A	0.9700
C4A—C4	1.492 (4)	C2—H2B	0.9700
C8A—C4B	1.512 (3)	C3—H3A	0.9700
C8A—C8	1.518 (4)	C3—H3B	0.9700
C8A—H13	0.9800	O4—H4	0.8200
C5—C4B	1.508 (4)	O5—C13	1.371 (3)
C5—C6	1.521 (5)	O5—H5	0.8200
C5—H5A	0.9700	C13—C12	1.373 (4)
C5—H5B	0.9700	C13—C14	1.391 (4)
C8—O3	1.204 (4)	C11—C12	1.388 (4)
C8—C7	1.507 (5)	C11—C10	1.388 (4)
C6—C7	1.532 (5)	C11—H19	0.9300
C6—H6A	0.9700	C10—C15	1.387 (4)
C6—H6B	0.9700	C14—C15	1.381 (4)
C1—O2	1.225 (4)	C14—H16	0.9300
C1—C2	1.502 (5)	C15—H15	0.9300
C4B—O4	1.416 (4)	C12—H18	0.9300
C4B—O1	1.443 (3)
C9A—C9—C10	110.6 (2)	C3—C4—H4A	109.5
C9A—C9—C8A	110.6 (2)	C4A—C4—H4B	109.5
C10—C9—C8A	110.0 (2)	C3—C4—H4B	109.5
C9A—C9—H9	108.5	H4A—C4—H4B	108.1
C10—C9—H9	108.5	C8—C7—C6	111.9 (3)
C8A—C9—H9	108.5	C8—C7—H7A	109.2
C4A—C9A—C1	119.1 (2)	C6—C7—H7A	109.2
C4A—C9A—C9	122.6 (2)	C8—C7—H7B	109.2
C1—C9A—C9	117.8 (2)	C6—C7—H7B	109.2
C9A—C4A—O1	123.3 (2)	H7A—C7—H7B	107.9
C9A—C4A—C4	124.6 (3)	C3—C2—C1	113.4 (3)
O1—C4A—C4	112.0 (2)	C3—C2—H2A	108.9
C4B—C8A—C8	109.8 (2)	C1—C2—H2A	108.9
C4B—C8A—C9	114.0 (2)	C3—C2—H2B	108.9
C8—C8A—C9	114.2 (2)	C1—C2—H2B	108.9
C4B—C8A—H13	106.0	H2A—C2—H2B	107.7
C8—C8A—H13	106.0	C2—C3—C4	111.7 (4)
C9—C8A—H13	106.0	C2—C3—H3A	109.3
C4B—C5—C6	109.9 (3)	C4—C3—H3A	109.3
C4B—C5—H5A	109.7	C2—C3—H3B	109.3
C6—C5—H5A	109.7	C4—C3—H3B	109.3
C4B—C5—H5B	109.7	H3A—C3—H3B	107.9
C6—C5—H5B	109.7	C4A—O1—C4B	114.3 (2)
H5A—C5—H5B	108.2	C4B—O4—H4	109.5
O3—C8—C7	123.7 (3)	C13—O5—H5	109.5
O3—C8—C8A	122.0 (3)	O5—C13—C12	122.5 (3)
C7—C8—C8A	114.2 (3)	O5—C13—C14	117.5 (2)
C5—C6—C7	111.1 (3)	C12—C13—C14	120.0 (2)
C5—C6—H6A	109.4	C12—C11—C10	121.2 (3)
C7—C6—H6A	109.4	C12—C11—H19	119.4
C5—C6—H6B	109.4	C10—C11—H19	119.4
C7—C6—H6B	109.4	C15—C10—C11	118.0 (2)
H6A—C6—H6B	108.0	C15—C10—C9	121.4 (2)
O2—C1—C9A	121.3 (3)	C11—C10—C9	120.6 (2)
O2—C1—C2	120.7 (3)	C15—C14—C13	119.6 (3)
C9A—C1—C2	117.9 (3)	C15—C14—H16	120.2
O4—C4B—O1	108.4 (2)	C13—C14—H16	120.2
O4—C4B—C5	111.4 (2)	C14—C15—C10	121.3 (3)
O1—C4B—C5	107.6 (2)	C14—C15—H15	119.3
O4—C4B—C8A	107.3 (2)	C10—C15—H15	119.3
O1—C4B—C8A	109.7 (2)	C13—C12—C11	119.8 (3)
C5—C4B—C8A	112.4 (2)	C13—C12—H18	120.1
C4A—C4—C3	110.8 (3)	C11—C12—H18	120.1
C4A—C4—H4A	109.5
C10—C9—C9A—C4A	118.8 (3)	C9—C8A—C4B—C5	174.6 (2)
C8A—C9—C9A—C4A	−3.4 (3)	C9A—C4A—C4—C3	15.5 (5)
C10—C9—C9A—C1	−68.9 (3)	O1—C4A—C4—C3	−163.9 (3)
C8A—C9—C9A—C1	169.0 (2)	O3—C8—C7—C6	132.1 (4)
C1—C9A—C4A—O1	−167.6 (3)	C8A—C8—C7—C6	−50.7 (4)
C9—C9A—C4A—O1	4.7 (4)	C5—C6—C7—C8	52.4 (4)
C1—C9A—C4A—C4	13.1 (4)	O2—C1—C2—C3	159.2 (4)
C9—C9A—C4A—C4	−174.7 (3)	C9A—C1—C2—C3	−24.1 (5)
C9A—C9—C8A—C4B	−26.3 (3)	C1—C2—C3—C4	52.2 (6)
C10—C9—C8A—C4B	−148.8 (2)	C4A—C4—C3—C2	−47.4 (5)
C9A—C9—C8A—C8	−153.6 (2)	C9A—C4A—O1—C4B	25.7 (4)
C10—C9—C8A—C8	83.9 (3)	C4—C4A—O1—C4B	−154.9 (2)
C4B—C8A—C8—O3	−131.1 (3)	O4—C4B—O1—C4A	62.6 (3)
C9—C8A—C8—O3	−1.7 (4)	C5—C4B—O1—C4A	−176.7 (2)
C4B—C8A—C8—C7	51.6 (3)	C8A—C4B—O1—C4A	−54.2 (3)
C9—C8A—C8—C7	−179.0 (3)	C12—C11—C10—C15	1.1 (4)
C4B—C5—C6—C7	−56.4 (4)	C12—C11—C10—C9	−177.3 (2)
C4A—C9A—C1—O2	167.8 (3)	C9A—C9—C10—C15	117.6 (3)
C9—C9A—C1—O2	−4.8 (4)	C8A—C9—C10—C15	−120.0 (2)
C4A—C9A—C1—C2	−8.8 (4)	C9A—C9—C10—C11	−64.0 (3)
C9—C9A—C1—C2	178.6 (3)	C8A—C9—C10—C11	58.4 (3)
C6—C5—C4B—O4	−61.1 (3)	O5—C13—C14—C15	−179.8 (3)
C6—C5—C4B—O1	−179.8 (2)	C12—C13—C14—C15	0.9 (4)
C6—C5—C4B—C8A	59.3 (3)	C13—C14—C15—C10	0.2 (4)
C8—C8A—C4B—O4	67.0 (3)	C11—C10—C15—C14	−1.1 (4)
C9—C8A—C4B—O4	−62.6 (3)	C9—C10—C15—C14	177.3 (2)
C8—C8A—C4B—O1	−175.5 (2)	O5—C13—C12—C11	179.8 (3)
C9—C8A—C4B—O1	54.9 (3)	C14—C13—C12—C11	−0.9 (4)
C8—C8A—C4B—C5	−55.9 (3)	C10—C11—C12—C13	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5i	0.82	2.07	2.852 (3)	160.
O5—H5···O2ii	0.82	1.94	2.758 (4)	175.
C4—H4B···O4iii	0.97	2.50	3.274 (5)	137.
C8A—H13···O3iv	0.98	2.59	3.535 (4)	161.
C12—H18···O2ii	0.93	2.55	3.251 (4)	132.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O5i	0.82	2.07	2.852 (3)	160
O5—H5⋯O2ii	0.82	1.94	2.758 (4)	175
C4—H4B⋯O4iii	0.97	2.50	3.274 (5)	137
C8A—H13⋯O3iv	0.98	2.59	3.535 (4)	161
C12—H18⋯O2ii	0.93	2.55	3.251 (4)	132

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .