14-Methoxy-2,16-dioxapentacyclo[7.7.5.0.0.0]henicosa-3(8),10,12,14-tetraene-7,20-dione.

The title compound, C(20)H(20)O(5), was synthesized from the reaction between 3-methoxysalicaldehyde and 1,3-cyclo-hexa-nedione in the presence of palladium(II) chloride. The two fused xanthene rings and one of the six-membered cyclo-hexane rings adopt envelope conformations, while the other six-membered cyclo-hexane ring is in a chair conformation. The mol-ecular packing is stabilized by weak inter-molecular C-H⋯O inter-actions.

Related literature

For applications of xanthene derivatives, see: Banerjee & Mukherjee (1981 ▶); Lambert et al. (1997 ▶); Hideo (1981 ▶); Poupelin et al. (1978 ▶); Menchen et al. (2003 ▶); Ravindranath & Seshadri (1973 ▶); Bigdeli et al. (2007 ▶). For the construction of xanthene derivatives, see: Fan et al. (2005 ▶); Jin et al. (2004 ▶, 2005 ▶); Srihari et al. (2008 ▶); Wang & Harvey (2002 ▶).

Experimental

Crystal data

C20H20O5

M = 340.36

Monoclinic,

a = 11.0939 (15) Å

b = 12.5918 (17) Å

c = 12.2982 (16) Å

β = 104.846 (2)°

V = 1660.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.32 × 0.28 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.970, T max = 0.976

10066 measured reflections

3882 independent reflections

2361 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.162

S = 1.06

3882 reflections

231 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 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/S1600536811028972/rk2283sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028972/rk2283Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028972/rk2283Isup3.cml

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

C20H20O5	Z = 4
Mr = 340.36	F(000) = 720
Monoclinic, P21/n	Dx = 1.361 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.0939 (15) Å	θ = 2.2–21.6°
b = 12.5918 (17) Å	µ = 0.10 mm−1
c = 12.2982 (16) Å	T = 298 K
β = 104.846 (2)°	Block, colourless
V = 1660.6 (4) Å3	0.32 × 0.28 × 0.25 mm

Bruker APEXII CCD diffractometer	3882 independent reflections
Radiation source: fine–focus sealed tube	2361 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ–and ω–scans	θmax = 27.8°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
Tmin = 0.970, Tmax = 0.976	k = −16→11
10066 measured reflections	l = −14→16

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0697P)2 + 0.3859P] where P = (Fo2 + 2Fc2)/3
3882 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.17 e Å−3
13 restraints	Δρmin = −0.19 e Å−3

Geometry. All s.u.'s (except the esd 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
O2	0.96704 (13)	0.21956 (12)	0.70094 (11)	0.0371 (4)
O4	1.10467 (13)	0.31569 (12)	0.62388 (13)	0.0395 (4)
O5	1.33022 (14)	0.38986 (14)	0.66951 (15)	0.0513 (5)
O1	0.66507 (16)	0.34312 (19)	0.54126 (17)	0.0729 (6)
O3	0.7943 (3)	0.52298 (18)	0.8256 (2)	0.0935 (8)
C6	0.88270 (19)	0.35355 (18)	0.55948 (17)	0.0342 (5)
H6	0.9002	0.3906	0.4951	0.041*
C5	0.98380 (18)	0.27078 (17)	0.59972 (16)	0.0327 (5)
C8	0.87449 (19)	0.37404 (19)	0.75482 (18)	0.0359 (5)
C14	1.0240 (2)	0.48114 (17)	0.68106 (17)	0.0338 (5)
C4	0.9797 (2)	0.18260 (18)	0.51593 (18)	0.0391 (5)
H4A	1.0458	0.1320	0.5462	0.047*
H4B	0.9936	0.2118	0.4471	0.047*
C15	1.12077 (19)	0.41893 (17)	0.66481 (16)	0.0322 (5)
C9	0.90857 (18)	0.27250 (19)	0.77017 (16)	0.0342 (5)
C16	1.2428 (2)	0.45815 (18)	0.68901 (18)	0.0365 (5)
C19	1.0504 (2)	0.58235 (19)	0.72677 (19)	0.0445 (6)
H19	0.9865	0.6244	0.7397	0.053*
C7	0.8944 (2)	0.43368 (19)	0.65409 (18)	0.0356 (5)
H7	0.830 (2)	0.4882 (19)	0.6303 (19)	0.046 (7)*
C1	0.7546 (2)	0.3018 (2)	0.52006 (19)	0.0448 (6)
C10	0.8860 (2)	0.2028 (2)	0.86036 (19)	0.0461 (6)
H10A	0.9640	0.1906	0.9164	0.055*
H10B	0.8545	0.1347	0.8286	0.055*
C17	1.2662 (2)	0.55933 (19)	0.73272 (18)	0.0429 (6)
H17	1.3468	0.5866	0.7487	0.051*
C18	1.1706 (3)	0.6203 (2)	0.75290 (19)	0.0477 (6)
H18	1.1877	0.6876	0.7844	0.057*
C2	0.7457 (2)	0.2024 (2)	0.4510 (2)	0.0528 (7)
H2A	0.7398	0.2221	0.3736	0.063*
H2B	0.6694	0.1655	0.4525	0.063*
C3	0.8546 (2)	0.1262 (2)	0.4899 (2)	0.0464 (6)
H3A	0.8461	0.0893	0.5568	0.056*
H3B	0.8520	0.0736	0.4317	0.056*
C13	0.8222 (3)	0.4294 (2)	0.8364 (2)	0.0585 (7)
C12	0.8086 (4)	0.3653 (3)	0.9354 (3)	0.0895 (12)
H12A	0.8816	0.3769	0.9973	0.107*
H12B	0.7368	0.3914	0.9587	0.107*
C20	1.4536 (2)	0.4297 (3)	0.6828 (3)	0.0754 (9)
H20A	1.4520	0.4869	0.6308	0.113*
H20B	1.5063	0.3738	0.6682	0.113*
H20C	1.4856	0.4551	0.7583	0.113*
C11	0.7939 (4)	0.2525 (3)	0.9151 (3)	0.0989 (13)
H11A	0.7107	0.2396	0.8679	0.119*
H11B	0.8001	0.2171	0.9864	0.119*

	U11	U22	U33	U12	U13	U23
O2	0.0418 (9)	0.0381 (9)	0.0328 (8)	0.0064 (7)	0.0117 (6)	0.0029 (7)
O4	0.0262 (8)	0.0316 (9)	0.0604 (10)	−0.0017 (6)	0.0108 (7)	−0.0086 (7)
O5	0.0303 (8)	0.0486 (11)	0.0760 (12)	−0.0051 (8)	0.0157 (8)	−0.0052 (9)
O1	0.0302 (9)	0.1070 (18)	0.0784 (14)	0.0033 (10)	0.0081 (9)	−0.0151 (12)
O3	0.144 (2)	0.0657 (15)	0.0981 (17)	0.0468 (15)	0.0806 (17)	0.0133 (13)
C6	0.0312 (11)	0.0402 (13)	0.0317 (11)	0.0022 (10)	0.0087 (8)	0.0055 (10)
C5	0.0298 (11)	0.0353 (12)	0.0333 (11)	−0.0017 (9)	0.0086 (8)	0.0006 (9)
C8	0.0303 (11)	0.0427 (14)	0.0371 (12)	0.0049 (10)	0.0131 (9)	0.0012 (10)
C14	0.0410 (12)	0.0317 (12)	0.0303 (10)	0.0014 (10)	0.0124 (9)	0.0031 (9)
C4	0.0431 (13)	0.0389 (13)	0.0385 (12)	−0.0052 (11)	0.0161 (10)	−0.0053 (10)
C15	0.0371 (12)	0.0286 (12)	0.0304 (10)	−0.0025 (10)	0.0077 (8)	−0.0013 (9)
C9	0.0272 (10)	0.0448 (13)	0.0300 (10)	0.0004 (10)	0.0062 (8)	0.0009 (10)
C16	0.0359 (12)	0.0381 (13)	0.0347 (11)	−0.0023 (10)	0.0075 (9)	0.0033 (10)
C19	0.0607 (16)	0.0334 (13)	0.0428 (13)	0.0032 (12)	0.0194 (11)	−0.0011 (11)
C7	0.0326 (11)	0.0385 (13)	0.0367 (11)	0.0082 (10)	0.0105 (9)	0.0031 (10)
C1	0.0342 (12)	0.0618 (17)	0.0355 (12)	−0.0007 (12)	0.0038 (9)	0.0083 (11)
C10	0.0445 (13)	0.0553 (16)	0.0393 (12)	0.0009 (12)	0.0124 (10)	0.0111 (11)
C17	0.0480 (14)	0.0404 (14)	0.0368 (12)	−0.0133 (12)	0.0047 (10)	0.0017 (10)
C18	0.0706 (18)	0.0333 (13)	0.0397 (13)	−0.0099 (13)	0.0152 (12)	−0.0059 (11)
C2	0.0446 (14)	0.0626 (18)	0.0461 (14)	−0.0180 (13)	0.0021 (11)	−0.0013 (13)
C3	0.0536 (15)	0.0446 (15)	0.0402 (13)	−0.0148 (12)	0.0106 (11)	−0.0061 (11)
C13	0.0661 (18)	0.0611 (19)	0.0597 (17)	0.0173 (15)	0.0371 (14)	0.0048 (14)
C12	0.134 (3)	0.085 (3)	0.077 (2)	0.027 (2)	0.078 (2)	0.0141 (19)
C20	0.0366 (15)	0.081 (2)	0.112 (3)	−0.0147 (15)	0.0260 (16)	−0.014 (2)
C11	0.127 (3)	0.102 (3)	0.090 (3)	0.030 (3)	0.075 (2)	0.040 (2)

O2—C9	1.369 (2)	C19—C18	1.375 (3)
O2—C5	1.456 (2)	C19—H19	0.9300
O4—C15	1.389 (3)	C7—H7	0.98 (2)
O4—C5	1.415 (2)	C1—C2	1.502 (4)
O5—C16	1.362 (3)	C10—C11	1.497 (4)
O5—C20	1.427 (3)	C10—H10A	0.9700
O1—C1	1.207 (3)	C10—H10B	0.9700
O3—C13	1.217 (3)	C17—C18	1.383 (3)
C6—C5	1.518 (3)	C17—H17	0.9300
C6—C7	1.520 (3)	C18—H18	0.9300
C6—C1	1.525 (3)	C2—C3	1.520 (4)
C6—H6	0.9800	C2—H2A	0.9700
C5—C4	1.508 (3)	C2—H2B	0.9700
C8—C9	1.333 (3)	C3—H3A	0.9700
C8—C13	1.459 (3)	C3—H3B	0.9700
C8—C7	1.512 (3)	C13—C12	1.501 (4)
C14—C15	1.385 (3)	C12—C11	1.445 (5)
C14—C19	1.393 (3)	C12—H12A	0.9700
C14—C7	1.513 (3)	C12—H12B	0.9700
C4—C3	1.519 (3)	C20—H20A	0.9600
C4—H4A	0.9700	C20—H20B	0.9600
C4—H4B	0.9700	C20—H20C	0.9600
C15—C16	1.400 (3)	C11—H11A	0.9700
C9—C10	1.485 (3)	C11—H11B	0.9700
C16—C17	1.381 (3)
C9—O2—C5	120.06 (17)	C2—C1—C6	117.2 (2)
C15—O4—C5	118.50 (16)	C9—C10—C11	110.7 (2)
C16—O5—C20	117.6 (2)	C9—C10—H10A	109.5
C5—C6—C7	107.17 (17)	C11—C10—H10A	109.5
C5—C6—C1	111.14 (19)	C9—C10—H10B	109.5
C7—C6—C1	114.61 (18)	C11—C10—H10B	109.5
C5—C6—H6	107.9	H10A—C10—H10B	108.1
C7—C6—H6	107.9	C16—C17—C18	120.4 (2)
C1—C6—H6	107.9	C16—C17—H17	119.8
O4—C5—O2	108.62 (15)	C18—C17—H17	119.8
O4—C5—C4	107.38 (16)	C19—C18—C17	120.5 (2)
O2—C5—C4	105.67 (17)	C19—C18—H18	119.7
O4—C5—C6	112.04 (17)	C17—C18—H18	119.7
O2—C5—C6	109.72 (16)	C1—C2—C3	114.61 (19)
C4—C5—C6	113.11 (18)	C1—C2—H2A	108.6
C9—C8—C13	120.6 (2)	C3—C2—H2A	108.6
C9—C8—C7	119.78 (19)	C1—C2—H2B	108.6
C13—C8—C7	119.5 (2)	C3—C2—H2B	108.6
C15—C14—C19	119.0 (2)	H2A—C2—H2B	107.6
C15—C14—C7	118.26 (19)	C4—C3—C2	112.4 (2)
C19—C14—C7	122.7 (2)	C4—C3—H3A	109.1
C5—C4—C3	110.74 (18)	C2—C3—H3A	109.1
C5—C4—H4A	109.5	C4—C3—H3B	109.1
C3—C4—H4A	109.5	C2—C3—H3B	109.1
C5—C4—H4B	109.5	H3A—C3—H3B	107.9
C3—C4—H4B	109.5	O3—C13—C8	121.5 (2)
H4A—C4—H4B	108.1	O3—C13—C12	122.3 (2)
C14—C15—O4	123.32 (19)	C8—C13—C12	116.2 (3)
C14—C15—C16	120.9 (2)	C11—C12—C13	114.8 (3)
O4—C15—C16	115.78 (19)	C11—C12—H12A	108.6
C8—C9—O2	122.79 (19)	C13—C12—H12A	108.6
C8—C9—C10	125.2 (2)	C11—C12—H12B	108.6
O2—C9—C10	112.0 (2)	C13—C12—H12B	108.6
O5—C16—C17	125.4 (2)	H12A—C12—H12B	107.6
O5—C16—C15	115.7 (2)	O5—C20—H20A	109.5
C17—C16—C15	118.9 (2)	O5—C20—H20B	109.5
C18—C19—C14	120.2 (2)	H20A—C20—H20B	109.5
C18—C19—H19	119.9	O5—C20—H20C	109.5
C14—C19—H19	119.9	H20A—C20—H20C	109.5
C8—C7—C14	110.26 (17)	H20B—C20—H20C	109.5
C8—C7—C6	107.20 (19)	C12—C11—C10	115.4 (3)
C14—C7—C6	108.63 (17)	C12—C11—H11A	108.4
C8—C7—H7	110.3 (13)	C10—C11—H11A	108.4
C14—C7—H7	111.4 (14)	C12—C11—H11B	108.4
C6—C7—H7	108.9 (13)	C10—C11—H11B	108.4
O1—C1—C2	122.9 (2)	H11A—C11—H11B	107.5
O1—C1—C6	119.9 (2)
C15—O4—C5—O2	−89.0 (2)	C9—C8—C7—C14	−86.9 (3)
C15—O4—C5—C4	157.18 (18)	C13—C8—C7—C14	90.9 (3)
C15—O4—C5—C6	32.4 (2)	C9—C8—C7—C6	31.1 (3)
C9—O2—C5—O4	96.3 (2)	C13—C8—C7—C6	−151.0 (2)
C9—O2—C5—C4	−148.79 (18)	C15—C14—C7—C8	86.9 (2)
C9—O2—C5—C6	−26.5 (2)	C19—C14—C7—C8	−89.8 (2)
C7—C6—C5—O4	−61.2 (2)	C15—C14—C7—C6	−30.4 (3)
C1—C6—C5—O4	172.89 (16)	C19—C14—C7—C6	153.0 (2)
C7—C6—C5—O2	59.6 (2)	C5—C6—C7—C8	−60.8 (2)
C1—C6—C5—O2	−66.4 (2)	C1—C6—C7—C8	63.0 (2)
C7—C6—C5—C4	177.27 (17)	C5—C6—C7—C14	58.3 (2)
C1—C6—C5—C4	51.3 (2)	C1—C6—C7—C14	−177.87 (18)
O4—C5—C4—C3	177.08 (18)	C5—C6—C1—O1	140.7 (2)
O2—C5—C4—C3	61.3 (2)	C7—C6—C1—O1	19.0 (3)
C6—C5—C4—C3	−58.8 (2)	C5—C6—C1—C2	−42.0 (3)
C19—C14—C15—O4	177.46 (19)	C7—C6—C1—C2	−163.7 (2)
C7—C14—C15—O4	0.7 (3)	C8—C9—C10—C11	13.6 (4)
C19—C14—C15—C16	−2.8 (3)	O2—C9—C10—C11	−165.0 (3)
C7—C14—C15—C16	−179.54 (18)	O5—C16—C17—C18	−177.6 (2)
C5—O4—C15—C14	−1.4 (3)	C15—C16—C17—C18	0.5 (3)
C5—O4—C15—C16	178.88 (17)	C14—C19—C18—C17	0.9 (3)
C13—C8—C9—O2	−174.7 (2)	C16—C17—C18—C19	−1.9 (3)
C7—C8—C9—O2	3.1 (3)	O1—C1—C2—C3	−142.9 (2)
C13—C8—C9—C10	6.9 (4)	C6—C1—C2—C3	39.8 (3)
C7—C8—C9—C10	−175.3 (2)	C5—C4—C3—C2	54.5 (3)
C5—O2—C9—C8	−5.9 (3)	C1—C2—C3—C4	−45.3 (3)
C5—O2—C9—C10	172.67 (17)	C9—C8—C13—O3	177.6 (3)
C20—O5—C16—C17	−7.7 (3)	C7—C8—C13—O3	−0.2 (4)
C20—O5—C16—C15	174.2 (2)	C9—C8—C13—C12	−0.6 (4)
C14—C15—C16—O5	−179.88 (18)	C7—C8—C13—C12	−178.4 (3)
O4—C15—C16—O5	−0.1 (3)	O3—C13—C12—C11	154.9 (4)
C14—C15—C16—C17	1.9 (3)	C8—C13—C12—C11	−26.9 (5)
O4—C15—C16—C17	−178.37 (19)	C13—C12—C11—C10	48.7 (5)
C15—C14—C19—C18	1.4 (3)	C9—C10—C11—C12	−41.1 (4)
C7—C14—C19—C18	178.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O5i	0.97	2.57	3.538 (4)	175.
C10—H10B···O3ii	0.97	2.59	3.466 (4)	151.
C10—H10A···O1iii	0.97	2.40	3.367 (3)	175.
C3—H3A···O3ii	0.97	2.52	3.389 (3)	149.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O5i	0.97	2.57	3.538 (4)	175
C10—H10B⋯O3ii	0.97	2.59	3.466 (4)	151
C10—H10A⋯O1iii	0.97	2.40	3.367 (3)	175
C3—H3A⋯O3ii	0.97	2.52	3.389 (3)	149

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