9-(3,4-Dimeth-oxy-phen-yl)-3,4,5,6,7,9-hexa-hydroxanthene-1,8(2H)-dione.

In the title compound, C(21)H(22)O(5), the mean planes of the pyran and dimeth-oxy-phenyl rings are nearly perpendicular to one another, with the dihedral angle between them being 88.21 (8)°. The pyran ring adopts a boat conformation whereas the two fused cyclo-hexane rings adopt envelope conformations. In the crystal, mol-ecules are linked into a three-dimensional network by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For condensation reactions between carbonyl compounds with active methyl­ene compounds, see: Chalais et al. (1985 ▶); Prajapati & Sanduh (1993 ▶); Texier-Boullet & Foucaud (1982 ▶); Jone (1967 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C21H22O5

M = 354.39

Monoclinic,

a = 8.7733 (3) Å

b = 15.2246 (5) Å

c = 14.6646 (4) Å

β = 116.891 (2)°

V = 1746.95 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.58 × 0.30 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.947, T max = 0.983

19254 measured reflections

5118 independent reflections

4066 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.130

S = 1.05

5118 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.28 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 datablocks global, I. DOI: 10.1107/S1600536811017867/bq2301sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017867/bq2301Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017867/bq2301Isup3.cml

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

C21H22O5	F(000) = 752
Mr = 354.39	Dx = 1.347 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6186 reflections
a = 8.7733 (3) Å	θ = 2.6–30.0°
b = 15.2246 (5) Å	µ = 0.10 mm−1
c = 14.6646 (4) Å	T = 100 K
β = 116.891 (2)°	Block, yellow
V = 1746.95 (10) Å3	0.58 × 0.30 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5118 independent reflections
Radiation source: fine-focus sealed tube	4066 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 30.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→9
Tmin = 0.947, Tmax = 0.983	k = −21→18
19254 measured reflections	l = −20→20

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0608P)2 + 0.471P] where P = (Fo2 + 2Fc2)/3
5118 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.28 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	−0.23678 (10)	0.45054 (6)	0.11930 (7)	0.0253 (2)
O2	−0.11008 (12)	0.63020 (7)	0.40709 (7)	0.0307 (2)
O3	0.34649 (11)	0.44914 (7)	0.36290 (7)	0.0293 (2)
O4	0.46323 (11)	0.77498 (6)	0.38751 (7)	0.0252 (2)
O5	0.31222 (11)	0.84133 (6)	0.20530 (7)	0.0254 (2)
C1	−0.16143 (15)	0.54404 (8)	0.26377 (9)	0.0212 (2)
C2	−0.21561 (16)	0.59572 (9)	0.32848 (10)	0.0240 (3)
C3	−0.40468 (17)	0.60323 (10)	0.29722 (11)	0.0296 (3)
H3A	−0.4278	0.6619	0.3173	0.035*
H3B	−0.4359	0.5588	0.3352	0.035*
C4	−0.51736 (17)	0.59051 (10)	0.18363 (11)	0.0317 (3)
H4A	−0.5069	0.6424	0.1461	0.038*
H4B	−0.6381	0.5859	0.1706	0.038*
C5	−0.46837 (16)	0.50797 (10)	0.14364 (10)	0.0269 (3)
H5A	−0.5066	0.4553	0.1672	0.032*
H5B	−0.5268	0.5083	0.0680	0.032*
C6	−0.27955 (15)	0.50362 (9)	0.18052 (9)	0.0220 (2)
C7	−0.06793 (15)	0.42479 (9)	0.15659 (9)	0.0219 (2)
C8	−0.04677 (16)	0.35533 (9)	0.09158 (10)	0.0259 (3)
H8A	−0.1171	0.3700	0.0185	0.031*
H8B	−0.0871	0.2984	0.1051	0.031*
C9	0.14076 (16)	0.34741 (9)	0.11409 (10)	0.0260 (3)
H9A	0.1567	0.2942	0.0805	0.031*
H9B	0.1739	0.3991	0.0862	0.031*
C10	0.25342 (16)	0.34178 (9)	0.22886 (10)	0.0263 (3)
H10A	0.2253	0.2876	0.2555	0.032*
H10B	0.3746	0.3381	0.2427	0.032*
C11	0.22973 (15)	0.42044 (8)	0.28392 (10)	0.0225 (2)
C12	0.05790 (14)	0.45987 (8)	0.24136 (9)	0.0205 (2)
C13	0.02759 (14)	0.53739 (8)	0.29541 (9)	0.0199 (2)
H13A	0.0892	0.5268	0.3708	0.024*
C14	0.09637 (14)	0.62177 (8)	0.27121 (9)	0.0200 (2)
C15	0.01165 (15)	0.66138 (9)	0.17626 (10)	0.0229 (3)
H15A	−0.0931	0.6372	0.1269	0.028*
C16	0.07768 (15)	0.73634 (8)	0.15190 (9)	0.0225 (3)
H16A	0.0175	0.7631	0.0867	0.027*
C17	0.23114 (15)	0.77157 (8)	0.22307 (9)	0.0213 (2)
C18	0.31465 (14)	0.73401 (8)	0.32119 (9)	0.0206 (2)
C19	0.24887 (14)	0.65911 (8)	0.34429 (9)	0.0210 (2)
H19A	0.3075	0.6330	0.4100	0.025*
C20	0.54591 (18)	0.74117 (11)	0.48942 (10)	0.0346 (3)
H20A	0.6472	0.7767	0.5304	0.052*
H20B	0.5804	0.6802	0.4879	0.052*
H20C	0.4668	0.7435	0.5198	0.052*
C21	0.23844 (18)	0.87415 (10)	0.10281 (10)	0.0292 (3)
H21A	0.2185	0.8253	0.0552	0.044*
H21B	0.3167	0.9165	0.0959	0.044*
H21C	0.1296	0.9031	0.0871	0.044*

	U11	U22	U33	U12	U13	U23
O1	0.0120 (4)	0.0367 (5)	0.0227 (4)	0.0006 (4)	0.0037 (3)	−0.0034 (4)
O2	0.0227 (5)	0.0359 (5)	0.0304 (5)	0.0013 (4)	0.0094 (4)	−0.0061 (4)
O3	0.0163 (4)	0.0326 (5)	0.0286 (5)	0.0025 (4)	0.0011 (4)	−0.0044 (4)
O4	0.0158 (4)	0.0308 (5)	0.0219 (4)	−0.0054 (4)	0.0021 (3)	−0.0042 (4)
O5	0.0195 (4)	0.0279 (5)	0.0243 (4)	−0.0053 (4)	0.0060 (4)	0.0001 (4)
C1	0.0141 (5)	0.0245 (6)	0.0237 (6)	0.0015 (4)	0.0072 (4)	0.0024 (5)
C2	0.0185 (5)	0.0238 (6)	0.0290 (6)	0.0017 (5)	0.0102 (5)	0.0021 (5)
C3	0.0197 (6)	0.0320 (7)	0.0388 (7)	0.0028 (5)	0.0148 (6)	−0.0020 (6)
C4	0.0181 (6)	0.0386 (8)	0.0367 (7)	0.0058 (5)	0.0108 (5)	0.0064 (6)
C5	0.0129 (5)	0.0376 (7)	0.0253 (6)	0.0017 (5)	0.0044 (5)	0.0022 (5)
C6	0.0139 (5)	0.0278 (6)	0.0230 (6)	0.0015 (5)	0.0071 (4)	0.0023 (5)
C7	0.0129 (5)	0.0268 (6)	0.0240 (6)	−0.0001 (4)	0.0065 (4)	0.0013 (5)
C8	0.0187 (6)	0.0313 (7)	0.0256 (6)	−0.0031 (5)	0.0082 (5)	−0.0054 (5)
C9	0.0188 (6)	0.0306 (7)	0.0284 (6)	−0.0010 (5)	0.0106 (5)	−0.0045 (5)
C10	0.0181 (6)	0.0266 (6)	0.0308 (7)	0.0027 (5)	0.0081 (5)	−0.0016 (5)
C11	0.0151 (5)	0.0238 (6)	0.0254 (6)	−0.0002 (4)	0.0065 (5)	0.0014 (5)
C12	0.0138 (5)	0.0229 (6)	0.0222 (5)	0.0005 (4)	0.0059 (4)	0.0007 (4)
C13	0.0121 (5)	0.0243 (6)	0.0199 (5)	0.0004 (4)	0.0043 (4)	0.0000 (4)
C14	0.0125 (5)	0.0241 (6)	0.0217 (5)	0.0013 (4)	0.0063 (4)	−0.0020 (4)
C15	0.0126 (5)	0.0263 (6)	0.0233 (6)	−0.0005 (4)	0.0023 (4)	−0.0013 (5)
C16	0.0159 (5)	0.0261 (6)	0.0204 (5)	0.0017 (5)	0.0039 (4)	0.0007 (5)
C17	0.0161 (5)	0.0227 (6)	0.0240 (6)	−0.0001 (4)	0.0081 (5)	−0.0030 (5)
C18	0.0112 (5)	0.0256 (6)	0.0214 (5)	−0.0005 (4)	0.0044 (4)	−0.0055 (5)
C19	0.0136 (5)	0.0270 (6)	0.0191 (5)	0.0018 (4)	0.0045 (4)	−0.0023 (4)
C20	0.0244 (7)	0.0513 (9)	0.0197 (6)	−0.0129 (6)	0.0027 (5)	−0.0044 (6)
C21	0.0289 (7)	0.0315 (7)	0.0244 (6)	−0.0070 (6)	0.0095 (5)	−0.0010 (5)

O1—C6	1.3800 (15)	C9—C10	1.5205 (19)
O1—C7	1.3836 (14)	C9—H9A	0.9900
O2—C2	1.2231 (16)	C9—H9B	0.9900
O3—C11	1.2283 (15)	C10—C11	1.5103 (18)
O4—C18	1.3738 (14)	C10—H10A	0.9900
O4—C20	1.4297 (16)	C10—H10B	0.9900
O5—C17	1.3674 (15)	C11—C12	1.4736 (16)
O5—C21	1.4309 (16)	C12—C13	1.5108 (17)
C1—C6	1.3411 (17)	C13—C14	1.5277 (17)
C1—C2	1.4676 (17)	C13—H13A	1.0000
C1—C13	1.5099 (16)	C14—C15	1.3852 (17)
C2—C3	1.5122 (17)	C14—C19	1.4017 (16)
C3—C4	1.517 (2)	C15—C16	1.3975 (18)
C3—H3A	0.9900	C15—H15A	0.9500
C3—H3B	0.9900	C16—C17	1.3851 (16)
C4—C5	1.528 (2)	C16—H16A	0.9500
C4—H4A	0.9900	C17—C18	1.4074 (17)
C4—H4B	0.9900	C18—C19	1.3874 (18)
C5—C6	1.4935 (17)	C19—H19A	0.9500
C5—H5A	0.9900	C20—H20A	0.9800
C5—H5B	0.9900	C20—H20B	0.9800
C7—C12	1.3446 (17)	C20—H20C	0.9800
C7—C8	1.4906 (18)	C21—H21A	0.9800
C8—C9	1.5294 (17)	C21—H21B	0.9800
C8—H8A	0.9900	C21—H21C	0.9800
C8—H8B	0.9900
C6—O1—C7	117.80 (9)	C9—C10—H10A	109.3
C18—O4—C20	116.55 (10)	C11—C10—H10B	109.3
C17—O5—C21	116.37 (10)	C9—C10—H10B	109.3
C6—C1—C2	119.46 (11)	H10A—C10—H10B	107.9
C6—C1—C13	122.55 (11)	O3—C11—C12	120.76 (12)
C2—C1—C13	117.98 (11)	O3—C11—C10	121.91 (11)
O2—C2—C1	120.73 (11)	C12—C11—C10	117.29 (11)
O2—C2—C3	120.81 (12)	C7—C12—C11	118.98 (11)
C1—C2—C3	118.43 (11)	C7—C12—C13	121.98 (10)
C2—C3—C4	113.83 (11)	C11—C12—C13	119.03 (10)
C2—C3—H3A	108.8	C1—C13—C12	108.70 (10)
C4—C3—H3A	108.8	C1—C13—C14	111.50 (10)
C2—C3—H3B	108.8	C12—C13—C14	110.69 (9)
C4—C3—H3B	108.8	C1—C13—H13A	108.6
H3A—C3—H3B	107.7	C12—C13—H13A	108.6
C3—C4—C5	111.70 (11)	C14—C13—H13A	108.6
C3—C4—H4A	109.3	C15—C14—C19	118.98 (11)
C5—C4—H4A	109.3	C15—C14—C13	120.72 (10)
C3—C4—H4B	109.3	C19—C14—C13	120.28 (11)
C5—C4—H4B	109.3	C14—C15—C16	121.10 (11)
H4A—C4—H4B	107.9	C14—C15—H15A	119.4
C6—C5—C4	110.85 (11)	C16—C15—H15A	119.4
C6—C5—H5A	109.5	C17—C16—C15	119.84 (11)
C4—C5—H5A	109.5	C17—C16—H16A	120.1
C6—C5—H5B	109.5	C15—C16—H16A	120.1
C4—C5—H5B	109.5	O5—C17—C16	124.70 (11)
H5A—C5—H5B	108.1	O5—C17—C18	115.81 (10)
C1—C6—O1	122.37 (10)	C16—C17—C18	119.48 (11)
C1—C6—C5	125.67 (12)	O4—C18—C19	124.51 (11)
O1—C6—C5	111.95 (11)	O4—C18—C17	115.33 (11)
C12—C7—O1	122.51 (11)	C19—C18—C17	120.13 (11)
C12—C7—C8	125.84 (11)	C18—C19—C14	120.35 (11)
O1—C7—C8	111.66 (10)	C18—C19—H19A	119.8
C7—C8—C9	110.54 (10)	C14—C19—H19A	119.8
C7—C8—H8A	109.5	O4—C20—H20A	109.5
C9—C8—H8A	109.5	O4—C20—H20B	109.5
C7—C8—H8B	109.5	H20A—C20—H20B	109.5
C9—C8—H8B	109.5	O4—C20—H20C	109.5
H8A—C8—H8B	108.1	H20A—C20—H20C	109.5
C10—C9—C8	109.91 (11)	H20B—C20—H20C	109.5
C10—C9—H9A	109.7	O5—C21—H21A	109.5
C8—C9—H9A	109.7	O5—C21—H21B	109.5
C10—C9—H9B	109.7	H21A—C21—H21B	109.5
C8—C9—H9B	109.7	O5—C21—H21C	109.5
H9A—C9—H9B	108.2	H21A—C21—H21C	109.5
C11—C10—C9	111.68 (11)	H21B—C21—H21C	109.5
C11—C10—H10A	109.3
C6—C1—C2—O2	176.94 (12)	C10—C11—C12—C13	178.63 (11)
C13—C1—C2—O2	−1.98 (19)	C6—C1—C13—C12	−17.44 (16)
C6—C1—C2—C3	−1.40 (18)	C2—C1—C13—C12	161.44 (11)
C13—C1—C2—C3	179.68 (11)	C6—C1—C13—C14	104.85 (14)
O2—C2—C3—C4	156.87 (13)	C2—C1—C13—C14	−76.26 (14)
C1—C2—C3—C4	−24.78 (18)	C7—C12—C13—C1	19.86 (16)
C2—C3—C4—C5	49.18 (16)	C11—C12—C13—C1	−158.95 (11)
C3—C4—C5—C6	−47.29 (15)	C7—C12—C13—C14	−102.92 (13)
C2—C1—C6—O1	−176.73 (11)	C11—C12—C13—C14	78.27 (13)
C13—C1—C6—O1	2.14 (19)	C1—C13—C14—C15	−47.46 (15)
C2—C1—C6—C5	2.0 (2)	C12—C13—C14—C15	73.68 (13)
C13—C1—C6—C5	−179.18 (12)	C1—C13—C14—C19	134.08 (11)
C7—O1—C6—C1	13.08 (18)	C12—C13—C14—C19	−104.78 (12)
C7—O1—C6—C5	−165.77 (11)	C19—C14—C15—C16	1.38 (18)
C4—C5—C6—C1	23.06 (18)	C13—C14—C15—C16	−177.10 (11)
C4—C5—C6—O1	−158.14 (11)	C14—C15—C16—C17	0.62 (19)
C6—O1—C7—C12	−10.48 (18)	C21—O5—C17—C16	−5.67 (18)
C6—O1—C7—C8	169.57 (11)	C21—O5—C17—C18	173.51 (11)
C12—C7—C8—C9	−16.76 (18)	C15—C16—C17—O5	175.93 (11)
O1—C7—C8—C9	163.19 (11)	C15—C16—C17—C18	−3.22 (18)
C7—C8—C9—C10	48.72 (15)	C20—O4—C18—C19	−5.34 (18)
C8—C9—C10—C11	−57.64 (15)	C20—O4—C18—C17	176.71 (11)
C9—C10—C11—O3	−148.95 (12)	O5—C17—C18—O4	2.67 (16)
C9—C10—C11—C12	33.42 (16)	C16—C17—C18—O4	−178.10 (11)
O1—C7—C12—C11	171.57 (11)	O5—C17—C18—C19	−175.38 (10)
C8—C7—C12—C11	−8.48 (19)	C16—C17—C18—C19	3.84 (18)
O1—C7—C12—C13	−7.24 (19)	O4—C18—C19—C14	−179.71 (11)
C8—C7—C12—C13	172.71 (12)	C17—C18—C19—C14	−1.85 (18)
O3—C11—C12—C7	−177.87 (12)	C15—C14—C19—C18	−0.75 (17)
C10—C11—C12—C7	−0.21 (17)	C13—C14—C19—C18	177.73 (10)
O3—C11—C12—C13	0.98 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O4i	0.99	2.41	3.3647 (18)	161
C5—H5A···O5ii	0.99	2.56	3.2366 (17)	126
C9—H9A···O2ii	0.99	2.55	3.3210 (17)	135
C10—H10B···O5iii	0.99	2.50	3.4822 (19)	173
C21—H21C···O2iv	0.98	2.57	3.1069 (18)	114

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O4i	0.99	2.41	3.3647 (18)	161
C5—H5A⋯O5ii	0.99	2.56	3.2366 (17)	126
C9—H9A⋯O2ii	0.99	2.55	3.3210 (17)	135
C10—H10B⋯O5iii	0.99	2.50	3.4822 (19)	173
C21—H21C⋯O2iv	0.98	2.57	3.1069 (18)	114

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