13c-Methoxy-1,2,3,13c-tetra­hydro­dibenzo­[a,kl]xanthan-1-one

Pang, J.-Y.; Cai, J.; Tan, D.-M.; Chen, Z.-P.; Xu, Z.-L.

doi:10.1107/S1600536802006414

13c-Methoxy-1,2,3,13c-tetrahydrodibenzo[a,kl]xanthan-1-one

J.-Y. Pang, J. Cai, D.-M. Tan, Z.-P. Chen and Z.-L. Xu

The title compound, C₂₁H₁₆O₃, is a key intermediate in the design of chiral amines. It is composed of three benzene rings and two other six-membered rings with a common chiral C atom. Racemic dimers are generated by C—H

O hydrogen bonds, formed by phenyl C—H groups and carbonyl O atoms.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802006414/bt6134sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802006414/bt6134Isup2.hkl Contains datablock I

CCDC reference: 185784

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.049
wR factor = 0.178
Data-to-parameter ratio = 14.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Comment top

Chiral amines are useful resolving agents, chiral building blocks and chiral auxiliaries in important stereoselective organic synthesis, such as asymmetric reduction, asymmetric epoxidation, asymmetric addition, asymmetric condensation, and resolution of racemic compounds. (Aldous et al., 2000; Kawamoto & Wills, 2000; Hashihayata et al., 1997; Dai et al., 2000; Enders & Ullrich, 2000). The title compound, (I), is a key intermediate for chiral amines that we are designing for potential use as chiral additives and auxiliaries in asymmetric synthesis. Information on the crystal structure (I) is useful for studying the stereoselection of its reductive amination reaction. Compound (I) was obtained by reduction of 1-oxo-13c-propoxy-1,13c-dihydrodibenzo[a,kl]xanthene(Tan et al., 2001) with hydrogen under Pd/C catalysis. The reduction reaction takes place at room temperature in high yield. The structure of (I) was also confirmed by ¹H NMR, ¹³C NMR, IR and FAB-MS spectroscopic analysis. As shown in Fig. 1, (I) is composed of five fused rings, with the methoxy group attached to a chiral C atom. The three aromatic rings are almost coplanar, while the six-membered ring adopts a twisted boat conformation, with the methoxy and carbonyl groups pointing in opposite directions from the phenyl plane. Weak intermolecular C—H···O hydrogen bonds formed by phenyl C—H groups and the carbonyl O atoms create racemic dimers which pack along the a axis, as shown in Fig. 2.

Experimental top

Compound (I) was obtained by reduction of 1-oxo-13c-methoxy-1,13c-dihydrodibenzo[a,kl]xanthene, (II), in ethyl acetate in the presence of hydrogen under Pd/C catalysis. (I) was the main product in a yield of 90%. A single-crystal suitable for X-ray analysis was recrystallized from methanol (m.p. 427–428 K). ν_max: 1727, 1581, 1456, 1267, 1066. δ_H (300 MHz in acetone/TMS): 2.61 (dt, J = 9.0 Hz, 17.7 Hz, 1H, –CH₂), 2.80 (s, 3H, OCH₃), 3.06 (dd, J = 8.4 Hz, 15.6 Hz 1H, –CH₂), 3.29 (dd, J = 9.0 Hz, 17.7 Hz, 1H, –CH₂), 3.88 (dt, J = 8.7 Hz, 15.9 Hz, 1H, –CH₂), 7.13–7.17 (m, 2H, H4, H6), 7.35 (d, J = 9.0 Hz, 1H, H9), 7.42–7.47 (m, 3H, H5, H10, H13), 7.88–7.91 (m, 1H, H11), 7.98 (d, J = 9.0 Hz, 1H, H8), 8.09–8.12 (m, 1H, H12). δ_C (300 MHz): 28.36 (CH₂), 30.52 (CH₂), 50.60 (OCH₃), 79.14 (13c-C), 109.28, 114.82, 116.95, 118.02, 123.86, 125.23, 126.85, 128.12, 129.20, 131.64, 131.92, 132.47, 133.29, 141.57, 152.09, 152.50, 203.08 (C═O). FAB–MS m/z (%): 317 (M⁺ + 1, 22), 316 (M⁺, 18), 285 (M⁺ –OCH₃, 58).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids.
	Fig. 2. The packing arrangement of (I) viewed along the a axis.

1-oxo-13c-methoxy-1,13c-dihydrodibenzo[a,kl]-xanthene top

Crystal data top

C₂₁H₁₆O₃	D_x = 1.354 Mg m⁻³
M_r = 316.34	Melting point: 427-428K K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.736 (4) Å	Cell parameters from 843 reflections
b = 11.104 (6) Å	θ = 3.9–24.9°
c = 18.183 (9) Å	µ = 0.09 mm⁻¹
β = 96.570 (11)°	T = 293 K
V = 1551.6 (14) Å³	Column, colorless
Z = 4	0.45 × 0.30 × 0.15 mm
F(000) = 664

Data collection top

Bruker SMART1000 CCD diffractometer	3166 independent reflections
Radiation source: fine-focus sealed tube	1817 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)	h = −8→9
T_min = 0.961, T_max = 0.987	k = −11→13
8639 measured reflections	l = −22→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.178	w = 1/[σ²(F_o²) + (0.1064P)² + 0.0469P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3166 reflections	Δρ_max = 0.19 e Å⁻³
218 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (3)

Crystal data top

C₂₁H₁₆O₃	V = 1551.6 (14) Å³
M_r = 316.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.736 (4) Å	µ = 0.09 mm⁻¹
b = 11.104 (6) Å	T = 293 K
c = 18.183 (9) Å	0.45 × 0.30 × 0.15 mm
β = 96.570 (11)°

Data collection top

Bruker SMART1000 CCD diffractometer	3166 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)	1817 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.987	R_int = 0.032
8639 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.178	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.19 e Å⁻³
3166 reflections	Δρ_min = −0.18 e Å⁻³
218 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.51108 (19)	0.89425 (14)	0.24474 (8)	0.0534 (4)
O2	0.02682 (18)	0.84231 (13)	0.29130 (8)	0.0463 (4)
O3	0.1503 (2)	1.11628 (15)	0.35660 (9)	0.0628 (5)
C1	0.3752 (3)	0.9294 (2)	0.19416 (12)	0.0485 (6)
C2	0.4122 (4)	0.9473 (2)	0.12249 (14)	0.0628 (7)
H2A	0.5213	0.9281	0.1089	0.075*
C3	0.2847 (4)	0.9942 (3)	0.07145 (14)	0.0738 (8)
H3A	0.3092	1.0084	0.0233	0.089*
C4	0.1214 (4)	1.0204 (2)	0.09044 (14)	0.0666 (7)
H4A	0.0379	1.0538	0.0555	0.080*
C5	0.0814 (3)	0.9972 (2)	0.16133 (12)	0.0513 (6)
C6	0.2114 (3)	0.94939 (18)	0.21410 (11)	0.0436 (5)
C7	0.1668 (3)	0.92797 (18)	0.29168 (11)	0.0418 (5)
C8	0.0826 (3)	1.04767 (19)	0.31029 (13)	0.0470 (6)
C9	−0.0833 (3)	1.0780 (2)	0.26218 (13)	0.0553 (6)
H9A	−0.0925	1.1648	0.2574	0.066*
H9B	−0.1813	1.0502	0.2865	0.066*
C10	−0.0951 (3)	1.0222 (2)	0.18475 (14)	0.0602 (7)
H10A	−0.1604	0.9476	0.1843	0.072*
H10B	−0.1577	1.0767	0.1495	0.072*
C11	0.0695 (3)	0.7243 (2)	0.27040 (14)	0.0585 (7)
H11A	−0.0299	0.6728	0.2717	0.088*
H11B	0.1642	0.6944	0.3041	0.088*
H11C	0.1029	0.7255	0.2212	0.088*
C12	0.4830 (3)	0.87999 (19)	0.31825 (12)	0.0456 (5)
C13	0.3243 (3)	0.89315 (18)	0.34337 (11)	0.0423 (5)
C14	0.3144 (3)	0.86835 (19)	0.42057 (12)	0.0461 (6)
C15	0.1566 (3)	0.8709 (2)	0.45268 (13)	0.0555 (6)
H15A	0.0545	0.8930	0.4238	0.067*
C16	0.1507 (4)	0.8417 (3)	0.52522 (14)	0.0675 (7)
H16A	0.0448	0.8432	0.5448	0.081*
C17	0.3016 (4)	0.8095 (3)	0.57033 (14)	0.0732 (8)
H17A	0.2958	0.7885	0.6195	0.088*
C18	0.4574 (4)	0.8088 (2)	0.54223 (13)	0.0669 (7)
H18A	0.5584	0.7900	0.5729	0.080*
C19	0.4669 (3)	0.8364 (2)	0.46712 (12)	0.0525 (6)
C20	0.6268 (3)	0.8297 (2)	0.43747 (14)	0.0592 (7)
H20A	0.7277	0.8115	0.4683	0.071*
C21	0.6353 (3)	0.8497 (2)	0.36420 (14)	0.0544 (6)
H21A	0.7409	0.8433	0.3447	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0425 (9)	0.0641 (10)	0.0552 (10)	0.0017 (7)	0.0122 (7)	0.0012 (8)
O2	0.0355 (8)	0.0410 (8)	0.0625 (10)	−0.0030 (6)	0.0060 (7)	0.0002 (7)
O3	0.0617 (11)	0.0549 (10)	0.0720 (11)	−0.0019 (8)	0.0088 (9)	−0.0165 (8)
C1	0.0460 (13)	0.0479 (13)	0.0521 (13)	−0.0032 (10)	0.0081 (11)	−0.0044 (10)
C2	0.0648 (17)	0.0718 (17)	0.0538 (15)	−0.0064 (13)	0.0159 (13)	−0.0040 (12)
C3	0.086 (2)	0.089 (2)	0.0483 (15)	−0.0110 (17)	0.0125 (15)	−0.0017 (14)
C4	0.0745 (19)	0.0727 (18)	0.0503 (15)	−0.0052 (14)	−0.0021 (13)	0.0044 (12)
C5	0.0533 (14)	0.0467 (13)	0.0524 (14)	−0.0041 (11)	0.0001 (11)	0.0000 (10)
C6	0.0463 (13)	0.0394 (11)	0.0451 (12)	−0.0041 (9)	0.0052 (10)	−0.0029 (9)
C7	0.0379 (11)	0.0388 (12)	0.0491 (12)	−0.0037 (9)	0.0066 (9)	−0.0021 (9)
C8	0.0426 (12)	0.0428 (13)	0.0573 (14)	−0.0036 (10)	0.0126 (10)	−0.0007 (10)
C9	0.0485 (14)	0.0471 (13)	0.0701 (16)	0.0069 (10)	0.0061 (11)	0.0054 (11)
C10	0.0501 (15)	0.0546 (15)	0.0730 (17)	0.0007 (11)	−0.0053 (12)	0.0047 (12)
C11	0.0565 (15)	0.0411 (13)	0.0767 (17)	−0.0043 (11)	0.0023 (12)	−0.0060 (12)
C12	0.0434 (13)	0.0439 (12)	0.0498 (13)	−0.0013 (10)	0.0065 (10)	−0.0011 (10)
C13	0.0367 (11)	0.0421 (12)	0.0485 (12)	−0.0003 (9)	0.0063 (9)	−0.0031 (9)
C14	0.0435 (13)	0.0462 (13)	0.0482 (13)	−0.0024 (10)	0.0034 (10)	−0.0050 (10)
C15	0.0522 (14)	0.0652 (16)	0.0494 (14)	0.0017 (11)	0.0070 (11)	−0.0020 (11)
C16	0.0667 (17)	0.084 (2)	0.0541 (15)	−0.0009 (14)	0.0160 (13)	−0.0021 (13)
C17	0.085 (2)	0.087 (2)	0.0476 (15)	−0.0007 (16)	0.0074 (14)	−0.0016 (13)
C18	0.0710 (19)	0.0742 (18)	0.0522 (16)	0.0011 (14)	−0.0081 (13)	−0.0025 (13)
C19	0.0508 (14)	0.0537 (14)	0.0514 (14)	−0.0009 (11)	−0.0015 (11)	−0.0045 (10)
C20	0.0440 (13)	0.0633 (16)	0.0675 (17)	−0.0005 (11)	−0.0059 (12)	−0.0020 (12)
C21	0.0380 (13)	0.0563 (15)	0.0687 (17)	0.0006 (10)	0.0053 (11)	−0.0026 (12)

Geometric parameters (Å, º) top

O1—C1	1.372 (3)	C10—H10A	0.9700
O1—C12	1.388 (3)	C10—H10B	0.9700
O2—C11	1.414 (3)	C11—H11A	0.9600
O2—C7	1.441 (2)	C11—H11B	0.9600
O3—C8	1.209 (3)	C11—H11C	0.9600
C1—C6	1.375 (3)	C12—C13	1.366 (3)
C1—C2	1.380 (3)	C12—C21	1.405 (3)
C2—C3	1.377 (4)	C13—C14	1.441 (3)
C2—H2A	0.9300	C14—C15	1.413 (3)
C3—C4	1.378 (4)	C14—C19	1.416 (3)
C3—H3A	0.9300	C15—C16	1.364 (3)
C4—C5	1.384 (3)	C15—H15A	0.9300
C4—H4A	0.9300	C16—C17	1.394 (4)
C5—C6	1.412 (3)	C16—H16A	0.9300
C5—C10	1.502 (3)	C17—C18	1.362 (4)
C6—C7	1.509 (3)	C17—H17A	0.9300
C7—C13	1.502 (3)	C18—C19	1.410 (3)
C7—C8	1.535 (3)	C18—H18A	0.9300
C8—C9	1.506 (3)	C19—C20	1.406 (3)
C9—C10	1.531 (3)	C20—C21	1.360 (3)
C9—H9A	0.9700	C20—H20A	0.9300
C9—H9B	0.9700	C21—H21A	0.9300

C1—O1—C12	119.08 (17)	C9—C10—H10B	109.2
C11—O2—C7	114.51 (16)	H10A—C10—H10B	107.9
O1—C1—C6	121.8 (2)	O2—C11—H11A	109.5
O1—C1—C2	116.6 (2)	O2—C11—H11B	109.5
C6—C1—C2	121.5 (2)	H11A—C11—H11B	109.5
C3—C2—C1	118.7 (3)	O2—C11—H11C	109.5
C3—C2—H2A	120.6	H11A—C11—H11C	109.5
C1—C2—H2A	120.6	H11B—C11—H11C	109.5
C2—C3—C4	121.2 (2)	C13—C12—O1	123.75 (19)
C2—C3—H3A	119.4	C13—C12—C21	123.5 (2)
C4—C3—H3A	119.4	O1—C12—C21	112.78 (19)
C3—C4—C5	120.2 (3)	C12—C13—C14	117.06 (19)
C3—C4—H4A	119.9	C12—C13—C7	120.95 (19)
C5—C4—H4A	119.9	C14—C13—C7	121.96 (18)
C4—C5—C6	119.0 (2)	C15—C14—C19	117.3 (2)
C4—C5—C10	122.5 (2)	C15—C14—C13	122.9 (2)
C6—C5—C10	118.5 (2)	C19—C14—C13	119.8 (2)
C1—C6—C5	119.2 (2)	C16—C15—C14	121.4 (2)
C1—C6—C7	122.51 (19)	C16—C15—H15A	119.3
C5—C6—C7	118.2 (2)	C14—C15—H15A	119.3
O2—C7—C13	112.86 (16)	C15—C16—C17	120.8 (3)
O2—C7—C6	110.61 (16)	C15—C16—H16A	119.6
C13—C7—C6	111.69 (18)	C17—C16—H16A	119.6
O2—C7—C8	103.61 (16)	C18—C17—C16	119.9 (2)
C13—C7—C8	114.79 (17)	C18—C17—H17A	120.1
C6—C7—C8	102.58 (16)	C16—C17—H17A	120.1
O3—C8—C9	122.4 (2)	C17—C18—C19	120.6 (2)
O3—C8—C7	122.6 (2)	C17—C18—H18A	119.7
C9—C8—C7	114.85 (18)	C19—C18—H18A	119.7
C8—C9—C10	113.63 (19)	C20—C19—C18	120.4 (2)
C8—C9—H9A	108.8	C20—C19—C14	119.5 (2)
C10—C9—H9A	108.8	C18—C19—C14	120.1 (2)
C8—C9—H9B	108.8	C21—C20—C19	120.7 (2)
C10—C9—H9B	108.8	C21—C20—H20A	119.7
H9A—C9—H9B	107.7	C19—C20—H20A	119.7
C5—C10—C9	112.0 (2)	C20—C21—C12	119.4 (2)
C5—C10—H10A	109.2	C20—C21—H21A	120.3
C9—C10—H10A	109.2	C12—C21—H21A	120.3
C5—C10—H10B	109.2

C12—O1—C1—C6	−0.9 (3)	C6—C5—C10—C9	41.0 (3)
C12—O1—C1—C2	177.24 (19)	C8—C9—C10—C5	−25.1 (3)
O1—C1—C2—C3	−173.6 (2)	C1—O1—C12—C13	3.4 (3)
C6—C1—C2—C3	4.5 (4)	C1—O1—C12—C21	−177.01 (19)
C1—C2—C3—C4	−1.5 (4)	O1—C12—C13—C14	176.40 (18)
C2—C3—C4—C5	−1.5 (4)	C21—C12—C13—C14	−3.1 (3)
C3—C4—C5—C6	1.6 (4)	O1—C12—C13—C7	−1.6 (3)
C3—C4—C5—C10	−179.1 (2)	C21—C12—C13—C7	178.86 (19)
O1—C1—C6—C5	173.61 (19)	O2—C7—C13—C12	123.1 (2)
C2—C1—C6—C5	−4.4 (3)	C6—C7—C13—C12	−2.2 (3)
O1—C1—C6—C7	−3.3 (3)	C8—C7—C13—C12	−118.5 (2)
C2—C1—C6—C7	178.67 (19)	O2—C7—C13—C14	−54.8 (3)
C4—C5—C6—C1	1.3 (3)	C6—C7—C13—C14	179.84 (18)
C10—C5—C6—C1	−178.01 (19)	C8—C7—C13—C14	63.6 (3)
C4—C5—C6—C7	178.3 (2)	C12—C13—C14—C15	−175.8 (2)
C10—C5—C6—C7	−1.0 (3)	C7—C13—C14—C15	2.2 (3)
C11—O2—C7—C13	−59.2 (2)	C12—C13—C14—C19	2.3 (3)
C11—O2—C7—C6	66.7 (2)	C7—C13—C14—C19	−179.69 (19)
C11—O2—C7—C8	176.02 (17)	C19—C14—C15—C16	−1.2 (3)
C1—C6—C7—O2	−122.0 (2)	C13—C14—C15—C16	177.0 (2)
C5—C6—C7—O2	61.1 (2)	C14—C15—C16—C17	0.7 (4)
C1—C6—C7—C13	4.6 (3)	C15—C16—C17—C18	1.0 (4)
C5—C6—C7—C13	−172.28 (18)	C16—C17—C18—C19	−2.2 (4)
C1—C6—C7—C8	128.1 (2)	C17—C18—C19—C20	−176.8 (2)
C5—C6—C7—C8	−48.8 (2)	C17—C18—C19—C14	1.7 (4)
O2—C7—C8—O3	132.9 (2)	C15—C14—C19—C20	178.5 (2)
C13—C7—C8—O3	9.4 (3)	C13—C14—C19—C20	0.2 (3)
C6—C7—C8—O3	−111.9 (2)	C15—C14—C19—C18	0.0 (3)
O2—C7—C8—C9	−51.9 (2)	C13—C14—C19—C18	−178.2 (2)
C13—C7—C8—C9	−175.41 (18)	C18—C19—C20—C21	176.3 (2)
C6—C7—C8—C9	63.2 (2)	C14—C19—C20—C21	−2.2 (4)
O3—C8—C9—C10	147.9 (2)	C19—C20—C21—C12	1.5 (4)
C7—C8—C9—C10	−27.2 (3)	C13—C12—C21—C20	1.3 (3)
C4—C5—C10—C9	−138.3 (2)	O1—C12—C21—C20	−178.3 (2)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆O₃
M_r	316.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.736 (4), 11.104 (6), 18.183 (9)
β (°)	96.570 (11)
V (Å³)	1551.6 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.45 × 0.30 × 0.15

Data collection
Diffractometer	Bruker SMART1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)
T_min, T_max	0.961, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	8639, 3166, 1817
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.178, 1.01
No. of reflections	3166
No. of parameters	218
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: SMART (Bruker, 1998), SMART, SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

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13c-Methoxy-1,2,3,13c-tetra­hydro­dibenzo­[a,kl]xanthan-1-one

Supporting information

Key indicators

checkCIF results

13c-Methoxy-1,2,3,13c-tetrahydrodibenzo[a,kl]xanthan-1-one