9-(4-Hy-droxy-phen-yl)-3,3,6,6-tetra-methyl-4,5,6,9-tetra-hydro-3H-xanthene-1,8(2H,7H)-dione.

In the title compound, C(23)H(26)O(4), the two cyclo-hexene rings adopt envelope conformations whereas the pyran ring adopts a boat conformation. In the crystal, pairs of inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into inversion dimers.

Related literature

For background to xanthene derivatives and their microbial activity, see: Jonathan et al. (1988 ▶); Hatakeyama et al. (1988 ▶); Shchekotikhin & Nikolaeva (2006 ▶); Hilderbrand & Weissleder (2007 ▶); Pohlers & Scaiano (1997 ▶); Knight & Stephens (1989 ▶); Reddy et al. (2010 ▶); Rathore et al. (2009 ▶); Rajesh et al. (2010 ▶); Mookiah et al. (2009 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Odabaşoğlu et al. (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C23H26O4

M = 366.44

Triclinic,

a = 9.3525 (1) Å

b = 10.2140 (1) Å

c = 11.6913 (1) Å

α = 67.271 (1)°

β = 76.119 (1)°

γ = 69.419 (1)°

V = 957.32 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.43 × 0.37 × 0.25 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.964, T max = 0.979

31226 measured reflections

8415 independent reflections

7287 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.119

S = 1.05

8415 reflections

252 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681102527X/is2739sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102527X/is2739Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681102527X/is2739Isup3.cml

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

C23H26O4	Z = 2
Mr = 366.44	F(000) = 392
Triclinic, P1	Dx = 1.271 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3525 (1) Å	Cell parameters from 9935 reflections
b = 10.2140 (1) Å	θ = 2.3–35.1°
c = 11.6913 (1) Å	µ = 0.09 mm−1
α = 67.271 (1)°	T = 100 K
β = 76.119 (1)°	Block, colourless
γ = 69.419 (1)°	0.43 × 0.37 × 0.25 mm
V = 957.32 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	8415 independent reflections
Radiation source: fine-focus sealed tube	7287 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 35.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.964, Tmax = 0.979	k = −14→16
31226 measured reflections	l = −17→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0652P)2 + 0.1943P] where P = (Fo2 + 2Fc2)/3
8415 reflections	(Δ/σ)max = 0.001
252 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1	0.34521 (6)	0.83032 (6)	0.99915 (5)	0.01579 (9)
O2	0.02841 (7)	1.17532 (6)	0.69020 (5)	0.02010 (11)
O3	−0.10300 (7)	0.70038 (7)	1.02725 (5)	0.02242 (11)
O4	0.16175 (7)	0.64603 (6)	0.49102 (5)	0.02133 (11)
C1	0.30785 (8)	0.95394 (7)	0.89677 (6)	0.01442 (11)
C2	0.42026 (8)	1.04139 (8)	0.85853 (6)	0.01674 (12)
H2A	0.5217	0.9742	0.8762	0.020*
H2B	0.3915	1.1068	0.9074	0.020*
C3	0.42656 (8)	1.13402 (7)	0.71914 (6)	0.01599 (11)
C4	0.26065 (9)	1.22259 (8)	0.69255 (7)	0.01843 (12)
H4A	0.2241	1.2977	0.7326	0.022*
H4B	0.2604	1.2733	0.6032	0.022*
C5	0.14947 (8)	1.13060 (7)	0.73661 (6)	0.01591 (11)
C6	0.18373 (8)	0.98961 (7)	0.83917 (6)	0.01459 (11)
C7	0.08188 (8)	0.88931 (7)	0.87495 (6)	0.01454 (11)
H7A	−0.0257	0.9474	0.8870	0.017*
C8	0.12303 (8)	0.76682 (7)	0.99633 (6)	0.01441 (11)
C9	0.02202 (8)	0.67001 (8)	1.06217 (6)	0.01635 (11)
C10	0.07186 (8)	0.53779 (8)	1.17715 (7)	0.01825 (12)
H10A	0.0404	0.4566	1.1776	0.022*
H10B	0.0174	0.5639	1.2507	0.022*
C11	0.24508 (8)	0.48275 (7)	1.18770 (6)	0.01565 (11)
C12	0.30063 (8)	0.61720 (7)	1.16306 (6)	0.01557 (11)
H12A	0.2626	0.6521	1.2341	0.019*
H12B	0.4122	0.5866	1.1551	0.019*
C13	0.24825 (8)	0.74137 (7)	1.04798 (6)	0.01417 (11)
C14	0.10119 (8)	0.82609 (7)	0.77113 (6)	0.01428 (11)
C15	−0.01107 (8)	0.87860 (7)	0.69164 (6)	0.01535 (11)
H15A	−0.1004	0.9526	0.7027	0.018*
C16	0.00783 (8)	0.82251 (7)	0.59602 (6)	0.01557 (11)
H16A	−0.0677	0.8601	0.5431	0.019*
C17	0.14000 (8)	0.70988 (7)	0.57955 (6)	0.01580 (11)
C18	0.25476 (8)	0.65753 (8)	0.65697 (7)	0.01858 (12)
H18A	0.3442	0.5839	0.6457	0.022*
C19	0.23478 (8)	0.71605 (8)	0.75134 (6)	0.01734 (12)
H19A	0.3120	0.6811	0.8023	0.021*
C20	0.50082 (11)	1.03502 (10)	0.63814 (8)	0.02510 (15)
H20A	0.5058	1.0956	0.5516	0.038*
H20B	0.4405	0.9697	0.6530	0.038*
H20C	0.6029	0.9775	0.6588	0.038*
C21	0.52047 (10)	1.24087 (8)	0.69189 (7)	0.02181 (14)
H21A	0.5222	1.3013	0.6053	0.033*
H21B	0.6238	1.1854	0.7104	0.033*
H21C	0.4745	1.3031	0.7429	0.033*
C22	0.33171 (9)	0.40175 (8)	1.09396 (7)	0.02121 (13)
H22A	0.2959	0.3178	1.1116	0.032*
H22B	0.4399	0.3687	1.1007	0.032*
H22C	0.3136	0.4680	1.0108	0.032*
C23	0.27504 (9)	0.37755 (8)	1.32038 (7)	0.02137 (13)
H23A	0.2417	0.2922	1.3380	0.032*
H23B	0.2191	0.4278	1.3792	0.032*
H23C	0.3831	0.3467	1.3271	0.032*
H1O4	0.0906 (19)	0.6959 (18)	0.4441 (15)	0.049 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0185 (2)	0.0151 (2)	0.0139 (2)	−0.00786 (17)	−0.00582 (16)	0.00009 (16)
O2	0.0238 (3)	0.0185 (2)	0.0186 (2)	−0.00527 (19)	−0.01005 (19)	−0.00298 (18)
O3	0.0192 (2)	0.0266 (3)	0.0221 (2)	−0.0106 (2)	−0.00590 (19)	−0.0033 (2)
O4	0.0263 (3)	0.0223 (2)	0.0170 (2)	−0.0028 (2)	−0.00794 (19)	−0.00877 (19)
C1	0.0185 (3)	0.0136 (2)	0.0116 (2)	−0.0058 (2)	−0.0037 (2)	−0.0025 (2)
C2	0.0210 (3)	0.0167 (3)	0.0145 (3)	−0.0092 (2)	−0.0052 (2)	−0.0022 (2)
C3	0.0206 (3)	0.0154 (3)	0.0131 (2)	−0.0077 (2)	−0.0017 (2)	−0.0040 (2)
C4	0.0225 (3)	0.0157 (3)	0.0155 (3)	−0.0072 (2)	−0.0050 (2)	−0.0005 (2)
C5	0.0208 (3)	0.0147 (2)	0.0126 (2)	−0.0050 (2)	−0.0049 (2)	−0.0034 (2)
C6	0.0178 (3)	0.0143 (2)	0.0121 (2)	−0.0057 (2)	−0.0042 (2)	−0.0026 (2)
C7	0.0156 (3)	0.0156 (2)	0.0129 (2)	−0.0051 (2)	−0.00397 (19)	−0.0033 (2)
C8	0.0163 (3)	0.0155 (2)	0.0119 (2)	−0.0062 (2)	−0.00282 (19)	−0.0031 (2)
C9	0.0173 (3)	0.0177 (3)	0.0148 (3)	−0.0072 (2)	−0.0019 (2)	−0.0044 (2)
C10	0.0176 (3)	0.0173 (3)	0.0177 (3)	−0.0072 (2)	−0.0021 (2)	−0.0018 (2)
C11	0.0175 (3)	0.0142 (2)	0.0152 (3)	−0.0060 (2)	−0.0028 (2)	−0.0032 (2)
C12	0.0195 (3)	0.0150 (2)	0.0128 (2)	−0.0070 (2)	−0.0047 (2)	−0.0018 (2)
C13	0.0169 (3)	0.0145 (2)	0.0121 (2)	−0.0066 (2)	−0.0024 (2)	−0.0032 (2)
C14	0.0157 (3)	0.0156 (2)	0.0125 (2)	−0.0058 (2)	−0.0036 (2)	−0.0034 (2)
C15	0.0158 (3)	0.0156 (2)	0.0150 (3)	−0.0046 (2)	−0.0048 (2)	−0.0036 (2)
C16	0.0176 (3)	0.0162 (3)	0.0137 (2)	−0.0059 (2)	−0.0055 (2)	−0.0027 (2)
C17	0.0197 (3)	0.0164 (3)	0.0120 (2)	−0.0065 (2)	−0.0035 (2)	−0.0033 (2)
C18	0.0182 (3)	0.0204 (3)	0.0161 (3)	−0.0019 (2)	−0.0052 (2)	−0.0065 (2)
C19	0.0164 (3)	0.0206 (3)	0.0151 (3)	−0.0035 (2)	−0.0051 (2)	−0.0057 (2)
C20	0.0305 (4)	0.0256 (3)	0.0223 (3)	−0.0114 (3)	0.0047 (3)	−0.0130 (3)
C21	0.0256 (3)	0.0196 (3)	0.0213 (3)	−0.0121 (3)	−0.0028 (3)	−0.0029 (3)
C22	0.0220 (3)	0.0194 (3)	0.0239 (3)	−0.0048 (2)	−0.0029 (3)	−0.0100 (3)
C23	0.0250 (3)	0.0172 (3)	0.0187 (3)	−0.0082 (2)	−0.0058 (2)	0.0011 (2)

O1—C1	1.3680 (8)	C11—C22	1.5314 (10)
O1—C13	1.3798 (8)	C11—C23	1.5324 (10)
O2—C5	1.2348 (9)	C11—C12	1.5371 (9)
O3—C9	1.2273 (9)	C12—C13	1.4897 (9)
O4—C17	1.3658 (8)	C12—H12A	0.9700
O4—H1O4	0.851 (17)	C12—H12B	0.9700
C1—C6	1.3498 (9)	C14—C15	1.3931 (9)
C1—C2	1.4930 (9)	C14—C19	1.3974 (10)
C2—C3	1.5349 (9)	C15—C16	1.3922 (9)
C2—H2A	0.9700	C15—H15A	0.9300
C2—H2B	0.9700	C16—C17	1.3948 (10)
C3—C20	1.5272 (10)	C16—H16A	0.9300
C3—C21	1.5280 (10)	C17—C18	1.3950 (10)
C3—C4	1.5330 (10)	C18—C19	1.3934 (10)
C4—C5	1.5116 (10)	C18—H18A	0.9300
C4—H4A	0.9700	C19—H19A	0.9300
C4—H4B	0.9700	C20—H20A	0.9600
C5—C6	1.4628 (9)	C20—H20B	0.9600
C6—C7	1.5152 (9)	C20—H20C	0.9600
C7—C8	1.5096 (9)	C21—H21A	0.9600
C7—C14	1.5302 (9)	C21—H21B	0.9600
C7—H7A	0.9800	C21—H21C	0.9600
C8—C13	1.3445 (9)	C22—H22A	0.9600
C8—C9	1.4773 (9)	C22—H22B	0.9600
C9—C10	1.5177 (10)	C22—H22C	0.9600
C10—C11	1.5354 (10)	C23—H23A	0.9600
C10—H10A	0.9700	C23—H23B	0.9600
C10—H10B	0.9700	C23—H23C	0.9600
C1—O1—C13	118.25 (5)	C10—C11—C12	108.40 (6)
C17—O4—H1O4	108.2 (11)	C13—C12—C11	112.63 (5)
C6—C1—O1	122.95 (6)	C13—C12—H12A	109.1
C6—C1—C2	125.29 (6)	C11—C12—H12A	109.1
O1—C1—C2	111.76 (5)	C13—C12—H12B	109.1
C1—C2—C3	112.06 (5)	C11—C12—H12B	109.1
C1—C2—H2A	109.2	H12A—C12—H12B	107.8
C3—C2—H2A	109.2	C8—C13—O1	123.08 (6)
C1—C2—H2B	109.2	C8—C13—C12	125.63 (6)
C3—C2—H2B	109.2	O1—C13—C12	111.29 (5)
H2A—C2—H2B	107.9	C15—C14—C19	118.00 (6)
C20—C3—C21	109.14 (6)	C15—C14—C7	121.39 (6)
C20—C3—C4	110.88 (6)	C19—C14—C7	120.59 (6)
C21—C3—C4	109.50 (6)	C16—C15—C14	121.28 (6)
C20—C3—C2	111.08 (6)	C16—C15—H15A	119.4
C21—C3—C2	109.08 (6)	C14—C15—H15A	119.4
C4—C3—C2	107.12 (6)	C15—C16—C17	120.04 (6)
C5—C4—C3	114.58 (6)	C15—C16—H16A	120.0
C5—C4—H4A	108.6	C17—C16—H16A	120.0
C3—C4—H4A	108.6	O4—C17—C16	122.64 (6)
C5—C4—H4B	108.6	O4—C17—C18	117.87 (6)
C3—C4—H4B	108.6	C16—C17—C18	119.48 (6)
H4A—C4—H4B	107.6	C19—C18—C17	119.72 (7)
O2—C5—C6	119.90 (6)	C19—C18—H18A	120.1
O2—C5—C4	120.92 (6)	C17—C18—H18A	120.1
C6—C5—C4	119.14 (6)	C18—C19—C14	121.44 (6)
C1—C6—C5	117.69 (6)	C18—C19—H19A	119.3
C1—C6—C7	122.86 (6)	C14—C19—H19A	119.3
C5—C6—C7	119.44 (6)	C3—C20—H20A	109.5
C8—C7—C6	108.86 (5)	C3—C20—H20B	109.5
C8—C7—C14	111.06 (5)	H20A—C20—H20B	109.5
C6—C7—C14	110.30 (5)	C3—C20—H20C	109.5
C8—C7—H7A	108.9	H20A—C20—H20C	109.5
C6—C7—H7A	108.9	H20B—C20—H20C	109.5
C14—C7—H7A	108.9	C3—C21—H21A	109.5
C13—C8—C9	118.04 (6)	C3—C21—H21B	109.5
C13—C8—C7	122.91 (6)	H21A—C21—H21B	109.5
C9—C8—C7	119.05 (6)	C3—C21—H21C	109.5
O3—C9—C8	120.20 (6)	H21A—C21—H21C	109.5
O3—C9—C10	120.86 (6)	H21B—C21—H21C	109.5
C8—C9—C10	118.87 (6)	C11—C22—H22A	109.5
C9—C10—C11	115.38 (6)	C11—C22—H22B	109.5
C9—C10—H10A	108.4	H22A—C22—H22B	109.5
C11—C10—H10A	108.4	C11—C22—H22C	109.5
C9—C10—H10B	108.4	H22A—C22—H22C	109.5
C11—C10—H10B	108.4	H22B—C22—H22C	109.5
H10A—C10—H10B	107.5	C11—C23—H23A	109.5
C22—C11—C23	109.53 (6)	C11—C23—H23B	109.5
C22—C11—C10	110.09 (6)	H23A—C23—H23B	109.5
C23—C11—C10	110.01 (6)	C11—C23—H23C	109.5
C22—C11—C12	110.94 (6)	H23A—C23—H23C	109.5
C23—C11—C12	107.83 (5)	H23B—C23—H23C	109.5
C13—O1—C1—C6	−2.38 (10)	C7—C8—C9—C10	174.00 (6)
C13—O1—C1—C2	177.69 (6)	O3—C9—C10—C11	161.59 (7)
C6—C1—C2—C3	−25.58 (10)	C8—C9—C10—C11	−21.61 (9)
O1—C1—C2—C3	154.34 (6)	C9—C10—C11—C22	−73.51 (7)
C1—C2—C3—C20	−69.86 (8)	C9—C10—C11—C23	165.69 (6)
C1—C2—C3—C21	169.79 (6)	C9—C10—C11—C12	48.00 (8)
C1—C2—C3—C4	51.36 (7)	C22—C11—C12—C13	72.05 (7)
C20—C3—C4—C5	69.49 (8)	C23—C11—C12—C13	−168.01 (6)
C21—C3—C4—C5	−170.02 (6)	C10—C11—C12—C13	−48.94 (7)
C2—C3—C4—C5	−51.86 (7)	C9—C8—C13—O1	−175.73 (6)
C3—C4—C5—O2	−157.76 (6)	C7—C8—C13—O1	4.22 (10)
C3—C4—C5—C6	24.75 (9)	C9—C8—C13—C12	4.00 (10)
O1—C1—C6—C5	175.35 (6)	C7—C8—C13—C12	−176.05 (6)
C2—C1—C6—C5	−4.74 (10)	C1—O1—C13—C8	3.14 (10)
O1—C1—C6—C7	−5.68 (10)	C1—O1—C13—C12	−176.62 (5)
C2—C1—C6—C7	174.24 (6)	C11—C12—C13—C8	25.26 (9)
O2—C5—C6—C1	−172.19 (6)	C11—C12—C13—O1	−154.98 (6)
C4—C5—C6—C1	5.34 (9)	C8—C7—C14—C15	134.11 (6)
O2—C5—C6—C7	8.80 (10)	C6—C7—C14—C15	−105.11 (7)
C4—C5—C6—C7	−173.67 (6)	C8—C7—C14—C19	−47.61 (8)
C1—C6—C7—C8	11.35 (9)	C6—C7—C14—C19	73.17 (8)
C5—C6—C7—C8	−169.70 (6)	C19—C14—C15—C16	0.67 (10)
C1—C6—C7—C14	−110.74 (7)	C7—C14—C15—C16	178.99 (6)
C5—C6—C7—C14	68.21 (8)	C14—C15—C16—C17	1.03 (10)
C6—C7—C8—C13	−10.62 (9)	C15—C16—C17—O4	177.02 (6)
C14—C7—C8—C13	111.01 (7)	C15—C16—C17—C18	−2.02 (10)
C6—C7—C8—C9	169.33 (6)	O4—C17—C18—C19	−177.79 (6)
C14—C7—C8—C9	−69.04 (8)	C16—C17—C18—C19	1.30 (11)
C13—C8—C9—O3	170.78 (7)	C17—C18—C19—C14	0.43 (11)
C7—C8—C9—O3	−9.17 (10)	C15—C14—C19—C18	−1.40 (10)
C13—C8—C9—C10	−6.04 (9)	C7—C14—C19—C18	−179.74 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O2i	0.851 (18)	1.910 (17)	2.7423 (9)	165.6 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O2i	0.851 (18)	1.910 (17)	2.7423 (9)	165.6 (17)

Symmetry code: (i) .