14-Methoxy-2,16-dioxapentacyclo[7.7.5.01,21.03,8.010,15]henicosa-3(8),10,12,14-tetraene-7,20-dione

Lu, W.; Lian, C.; Yang, Y.; Zhu, Y.

doi:10.1107/S1600536811028972

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2108

doi:10.1107/S1600536811028972

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14-Methoxy-2,16-dioxapentacyclo[7.7.5.0^1,21.0^3,8.0^10,15]henicosa-3(8),10,12,14-tetraene-7,20-dione

Weicheng Lu,^a Chaomei Lian,^a Yan Yang ^a and Yulin Zhu ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: yulinzhu2002@yahoo.com.cn

(Received 30 June 2011; accepted 18 July 2011; online 23 July 2011)

The title compound, C₂₀H₂₀O₅, was synthesized from the reaction between 3-methoxysalicaldehyde and 1,3–cyclohexanedione in the presence of palladium(II) chloride. The two fused xanthene rings and one of the six-membered cyclohexane rings adopt envelope conformations, while the other six-membered cyclohexane ring is in a chair conformation. The molecular packing is stabilized by weak intermolecular C—H⋯O interactions.

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_r = 340.36
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.057
wR(F²) = 0.162
S = 1.06
3882 reflections
231 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811028972/rk2283sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811028972/rk2283Isup3.cml

checkCIF report

Comment top

Xanthenes and benzoxanthenes are important biologically active heterocyclic compounds, which possess antiviral, anti–inflammatory and antibacterial activities (Banerjee & Mukherjee 1981; Lambert et al., 1997; Hideo 1981; Poupelin et al., 1978; Menchen et al., 2003; Ravindranath & Seshadri 1973). They are also implicated in photodynamic therapy, examples including myrtucommulone–E, chromenes, rhodomyrtone (Bigdeli et al., 2007). Various literature procedures are available to synthesis xanthenes (Fan et al., 2005; Jin et al., 2004, 2005; Srihari et al., 2008; Wang & Harvey 2002). In the presence of palladium(II) chloride, the reaction between 3–methoxysalicyladehyde and 1,3–cyclohexanedione proceeded to give the title compound (Fig. 1). The molecular structure of the title compound is illustrated in Fig. 2. There are no unusual bond lengths and angles in the compound. The title molecule is built up from five fused rings via phenyl, xanthene, and cyclohexane. The two fused xanthene rings adopt envelope conformations, one of the six–membered cyclohexane rings is also in an envelope conformation and the other is in chair conformations. In addition, the molecules in the structure are linked via paired C18—H2A, O3—H10B, O1—H20B et al. short–contaction force.

Related literature top

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 top

A mixture of 3–methoxysalicyladehyde (0.76 g, 5 mmol), 1,3–cyclohexanedione (1.12 g, 10 mmol), and palladium(II) chloride (0.002 g) was refluxed in acetonitrile (12 ml) at 353 K for 12 h. After being cooled to room temperature, the reaction mixture was poured into water. The white precipitate was filtered off with a silica pad, washed twice with cool water, and the filtrate was then dried under vacuum to yield the product in yield of 90%. Single crystals of the title compound were obtained by slow evaporation from ethanol at room temperature to yield colourless, block–shaped crystal.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Palladium(II) chloride catalyzed synthesis of the title compound.
	Fig. 2. View of the title compound showing the atom–labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.

14-Methoxy-2,16-dioxapentacyclo[7.7.5.0^1,21.0^3,8.0^10,15]henicosa- 3(8),10,12,14-tetraene-7,20-dione top

Crystal data top

C₂₀H₂₀O₅	Z = 4
M_r = 340.36	F(000) = 720
Monoclinic, P2₁/n	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0697P)² + 0.3859P] where P = (F_o² + 2F_c²)/3
3882 reflections	(Δ/σ)_max < 0.001
231 parameters	Δρ_max = 0.17 e Å⁻³
13 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₀H₂₀O₅	V = 1660.6 (4) Å³
M_r = 340.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.0939 (15) Å	µ = 0.10 mm⁻¹
b = 12.5918 (17) Å	T = 298 K
c = 12.2982 (16) Å	0.32 × 0.28 × 0.25 mm
β = 104.846 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3882 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2361 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.976	R_int = 0.035
10066 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	13 restraints
wR(F²) = 0.162	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.17 e Å⁻³
3882 reflections	Δρ_min = −0.19 e Å⁻³
231 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, z+1/2; (ii) −x+3/2, y−1/2, −z+3/2; (iii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀O₅
M_r	340.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.0939 (15), 12.5918 (17), 12.2982 (16)
β (°)	104.846 (2)
V (Å³)	1660.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.32 × 0.28 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.970, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	10066, 3882, 2361
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.656

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.162, 1.06
No. of reflections	3882
No. of parameters	231
No. of restraints	13
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O5ⁱ	0.97	2.57	3.538 (4)	174.5
C10—H10B···O3ⁱⁱ	0.97	2.59	3.466 (4)	150.8
C10—H10A···O1ⁱⁱⁱ	0.97	2.40	3.367 (3)	174.8
C3—H3A···O3ⁱⁱ	0.97	2.52	3.389 (3)	148.5

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) −x+3/2, y−1/2, −z+3/2; (iii) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The authors thank South China Normal University for financial support (grant SCNUG21096).

References

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Volume 67| Part 8| August 2011| Page o2108

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

14-Meth­oxy-2,16-dioxa­penta­cyclo[7.7.5.01,21.03,8.010,15]henicosa-3(8),10,12,14-tetra­ene-7,20-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

14-Methoxy-2,16-dioxapentacyclo[7.7.5.0^1,21.0^3,8.0^10,15]henicosa-3(8),10,12,14-tetraene-7,20-dione