3,3,6,6-Tetra-methyl-9-phenyl-3,4,5,6-tetra-hydro-9H-xanthene-1,8(2H,7H)-dione.

In the title compound, C(23)H(26)O(3), the three six-membered rings of the xanthene system are non-planar, having total puckering amplitudes, Q(T), of 0.443 (2), 0.202 (2) and 0.449 (2) Å. The central ring adopts a boat conformation and the outer rings adopt sofa conformations. The crystal structure is stabilized by van der Waals inter-actions.

Related literature

For the biological and pharmaceutical properties of xanthenes, see: Hideo (1981 ▶); Lambert et al. (1997 ▶); Poupelin et al. (1978 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C23H26O3

M = 350.44

Monoclinic,

a = 6.0562 (5) Å

b = 19.7680 (18) Å

c = 16.4325 (13) Å

β = 97.924 (3)°

V = 1948.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.17 × 0.15 × 0.11 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.987, T max = 0.992

11861 measured reflections

4284 independent reflections

2825 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.138

S = 1.03

4284 reflections

239 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010526/at2748sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010526/at2748Isup2.hkl

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

C23H26O3	F(000) = 752
Mr = 350.44	Dx = 1.195 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2500 reflections
a = 6.0562 (5) Å	θ = 2–27°
b = 19.7680 (18) Å	µ = 0.08 mm−1
c = 16.4325 (13) Å	T = 293 K
β = 97.924 (3)°	Needle, colourless
V = 1948.5 (3) Å3	0.17 × 0.15 × 0.11 mm
Z = 4

Bruker SMART APEX CCD diffractometer	4284 independent reflections
Radiation source: fine-focus sealed tube	2825 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω scans	θmax = 27.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −5→7
Tmin = 0.987, Tmax = 0.992	k = −25→25
11861 measured reflections	l = −21→12

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0661P)2 + 0.1411P] where P = (Fo2 + 2Fc2)/3
4284 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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
C2	0.2342 (3)	0.26716 (7)	0.39187 (9)	0.0364 (4)
C3	0.0380 (2)	0.27207 (7)	0.34340 (9)	0.0353 (3)
C4	−0.0306 (3)	0.22377 (7)	0.27309 (9)	0.0363 (4)
H4	−0.1866	0.2110	0.2741	0.044*
C5	0.1110 (3)	0.16067 (8)	0.28674 (9)	0.0379 (4)
C6	0.3004 (3)	0.15872 (7)	0.33973 (9)	0.0390 (4)
C7	0.3232 (3)	0.31533 (8)	0.45793 (9)	0.0424 (4)
H7A	0.4811	0.3220	0.4562	0.051*
H7B	0.3068	0.2956	0.5108	0.051*
C8	0.2064 (3)	0.38413 (8)	0.45065 (10)	0.0450 (4)
C9	−0.0457 (3)	0.37197 (10)	0.43150 (11)	0.0544 (5)
H9A	−0.0970	0.3516	0.4792	0.065*
H9B	−0.1199	0.4153	0.4221	0.065*
C10	−0.1139 (3)	0.32744 (9)	0.35821 (10)	0.0447 (4)
C11	0.0384 (3)	0.09875 (8)	0.24133 (10)	0.0479 (4)
C12	0.1983 (4)	0.03983 (9)	0.24839 (11)	0.0607 (5)
H12A	0.2987	0.0452	0.2077	0.073*
H12B	0.1141	−0.0014	0.2355	0.073*
C13	0.3369 (3)	0.03208 (8)	0.33293 (10)	0.0497 (4)
C14	0.4530 (3)	0.09951 (8)	0.35552 (11)	0.0504 (4)
H14A	0.5142	0.0988	0.4133	0.060*
H14B	0.5761	0.1048	0.3240	0.060*
C15	−0.0128 (3)	0.25771 (7)	0.19070 (9)	0.0360 (4)
C16	0.1833 (3)	0.28868 (9)	0.17640 (10)	0.0457 (4)
H16	0.3073	0.2874	0.2167	0.055*
C17	0.1970 (3)	0.32159 (9)	0.10281 (11)	0.0534 (5)
H17	0.3297	0.3421	0.0939	0.064*
C18	0.0143 (4)	0.32390 (9)	0.04283 (11)	0.0562 (5)
H18	0.0228	0.3465	−0.0063	0.067*
C19	−0.1807 (3)	0.29273 (10)	0.05584 (11)	0.0601 (5)
H19	−0.3039	0.2939	0.0153	0.072*
C20	−0.1939 (3)	0.25964 (9)	0.12930 (10)	0.0495 (4)
H20	−0.3261	0.2384	0.1375	0.059*
C21	0.2861 (3)	0.42570 (9)	0.38171 (13)	0.0613 (5)
H21A	0.2137	0.4690	0.3783	0.092*
H21B	0.2502	0.4022	0.3305	0.092*
H21C	0.4446	0.4319	0.3931	0.092*
C22	0.2621 (4)	0.42158 (12)	0.53235 (13)	0.0775 (7)
H22A	0.4210	0.4241	0.5467	0.116*
H22B	0.1990	0.3977	0.5745	0.116*
H22C	0.2012	0.4665	0.5271	0.116*
C23	0.5131 (4)	−0.02346 (10)	0.32996 (14)	0.0785 (7)
H23A	0.4405	−0.0654	0.3136	0.118*
H23B	0.5982	−0.0285	0.3834	0.118*
H23C	0.6106	−0.0111	0.2910	0.118*
C24	0.1837 (4)	0.01311 (11)	0.39644 (13)	0.0756 (6)
H24A	0.1096	−0.0288	0.3808	0.113*
H24B	0.0748	0.0481	0.3987	0.113*
H24C	0.2710	0.0082	0.4495	0.113*
O1	0.37769 (18)	0.21342 (5)	0.38742 (7)	0.0448 (3)
O2	−0.2918 (2)	0.33452 (7)	0.31414 (8)	0.0672 (4)
O3	−0.1434 (2)	0.09604 (6)	0.19873 (9)	0.0699 (4)

	U11	U22	U33	U12	U13	U23
C2	0.0412 (9)	0.0298 (8)	0.0381 (8)	0.0020 (7)	0.0052 (7)	0.0017 (6)
C3	0.0360 (8)	0.0329 (8)	0.0367 (8)	0.0003 (7)	0.0043 (6)	−0.0007 (6)
C4	0.0323 (8)	0.0352 (8)	0.0397 (8)	−0.0005 (7)	−0.0007 (6)	−0.0004 (6)
C5	0.0453 (9)	0.0316 (8)	0.0358 (8)	0.0009 (7)	0.0018 (7)	0.0005 (6)
C6	0.0431 (9)	0.0298 (8)	0.0428 (8)	0.0002 (7)	0.0018 (7)	−0.0019 (7)
C7	0.0490 (10)	0.0378 (9)	0.0388 (8)	−0.0017 (8)	−0.0003 (7)	−0.0023 (7)
C8	0.0460 (10)	0.0368 (9)	0.0524 (10)	0.0014 (8)	0.0074 (8)	−0.0094 (7)
C9	0.0492 (11)	0.0530 (11)	0.0636 (11)	0.0044 (9)	0.0172 (9)	−0.0163 (9)
C10	0.0398 (9)	0.0451 (10)	0.0501 (9)	0.0030 (8)	0.0096 (8)	−0.0026 (8)
C11	0.0638 (12)	0.0382 (9)	0.0386 (9)	−0.0004 (8)	−0.0042 (8)	−0.0007 (7)
C12	0.0880 (15)	0.0391 (10)	0.0497 (10)	0.0125 (10)	−0.0097 (10)	−0.0101 (8)
C13	0.0689 (12)	0.0319 (9)	0.0455 (9)	0.0069 (8)	−0.0020 (8)	−0.0009 (7)
C14	0.0518 (10)	0.0384 (9)	0.0579 (10)	0.0084 (8)	−0.0028 (8)	−0.0019 (8)
C15	0.0395 (8)	0.0305 (8)	0.0363 (8)	0.0027 (7)	−0.0006 (6)	−0.0030 (6)
C16	0.0452 (10)	0.0467 (10)	0.0440 (9)	−0.0038 (8)	0.0018 (7)	−0.0049 (8)
C17	0.0653 (12)	0.0435 (10)	0.0540 (10)	−0.0106 (9)	0.0178 (9)	−0.0038 (8)
C18	0.0869 (15)	0.0412 (10)	0.0406 (9)	0.0031 (10)	0.0093 (9)	0.0046 (8)
C19	0.0665 (13)	0.0629 (12)	0.0457 (10)	0.0049 (11)	−0.0113 (9)	0.0072 (9)
C20	0.0447 (10)	0.0511 (11)	0.0491 (10)	−0.0035 (8)	−0.0065 (8)	0.0037 (8)
C21	0.0562 (12)	0.0397 (10)	0.0881 (14)	0.0017 (9)	0.0101 (10)	0.0126 (10)
C22	0.0799 (16)	0.0678 (14)	0.0827 (15)	0.0012 (12)	0.0036 (12)	−0.0377 (12)
C23	0.1014 (17)	0.0442 (11)	0.0823 (15)	0.0268 (12)	−0.0138 (13)	−0.0109 (10)
C24	0.0986 (17)	0.0577 (13)	0.0692 (13)	−0.0073 (12)	0.0070 (12)	0.0173 (10)
O1	0.0426 (6)	0.0322 (6)	0.0551 (7)	0.0053 (5)	−0.0092 (5)	−0.0062 (5)
O2	0.0462 (8)	0.0734 (10)	0.0784 (9)	0.0206 (7)	−0.0042 (7)	−0.0149 (7)
O3	0.0744 (10)	0.0486 (8)	0.0766 (9)	−0.0028 (7)	−0.0251 (8)	−0.0129 (7)

C2—C3	1.340 (2)	C13—C24	1.536 (3)
C2—O1	1.3809 (17)	C13—C23	1.536 (3)
C2—C7	1.488 (2)	C14—H14A	0.9700
C3—C10	1.471 (2)	C14—H14B	0.9700
C3—C4	1.512 (2)	C15—C20	1.384 (2)
C4—C5	1.513 (2)	C15—C16	1.385 (2)
C4—C15	1.528 (2)	C16—C17	1.386 (2)
C4—H4	0.9800	C16—H16	0.9300
C5—C6	1.341 (2)	C17—C18	1.377 (3)
C5—C11	1.469 (2)	C17—H17	0.9300
C6—O1	1.3788 (18)	C18—C19	1.375 (3)
C6—C14	1.492 (2)	C18—H18	0.9300
C7—C8	1.530 (2)	C19—C20	1.385 (2)
C7—H7A	0.9700	C19—H19	0.9300
C7—H7B	0.9700	C20—H20	0.9300
C8—C22	1.529 (2)	C21—H21A	0.9600
C8—C21	1.531 (2)	C21—H21B	0.9600
C8—C9	1.534 (2)	C21—H21C	0.9600
C9—C10	1.503 (2)	C22—H22A	0.9600
C9—H9A	0.9700	C22—H22B	0.9600
C9—H9B	0.9700	C22—H22C	0.9600
C10—O2	1.221 (2)	C23—H23A	0.9600
C11—O3	1.222 (2)	C23—H23B	0.9600
C11—C12	1.509 (2)	C23—H23C	0.9600
C12—C13	1.529 (2)	C24—H24A	0.9600
C12—H12A	0.9700	C24—H24B	0.9600
C12—H12B	0.9700	C24—H24C	0.9600
C13—C14	1.529 (2)
C3—C2—O1	122.50 (13)	C14—C13—C23	109.43 (16)
C3—C2—C7	126.13 (14)	C24—C13—C23	109.54 (17)
O1—C2—C7	111.33 (13)	C6—C14—C13	112.88 (14)
C2—C3—C10	118.61 (14)	C6—C14—H14A	109.0
C2—C3—C4	122.44 (13)	C13—C14—H14A	109.0
C10—C3—C4	118.94 (13)	C6—C14—H14B	109.0
C3—C4—C5	108.46 (12)	C13—C14—H14B	109.0
C3—C4—C15	110.74 (12)	H14A—C14—H14B	107.8
C5—C4—C15	112.66 (12)	C20—C15—C16	118.41 (14)
C3—C4—H4	108.3	C20—C15—C4	120.80 (14)
C5—C4—H4	108.3	C16—C15—C4	120.77 (13)
C15—C4—H4	108.3	C15—C16—C17	120.76 (16)
C6—C5—C11	118.38 (14)	C15—C16—H16	119.6
C6—C5—C4	122.44 (13)	C17—C16—H16	119.6
C11—C5—C4	119.17 (14)	C18—C17—C16	120.09 (17)
C5—C6—O1	122.64 (13)	C18—C17—H17	120.0
C5—C6—C14	126.09 (14)	C16—C17—H17	120.0
O1—C6—C14	111.27 (13)	C19—C18—C17	119.77 (16)
C2—C7—C8	113.26 (13)	C19—C18—H18	120.1
C2—C7—H7A	108.9	C17—C18—H18	120.1
C8—C7—H7A	108.9	C18—C19—C20	120.08 (17)
C2—C7—H7B	108.9	C18—C19—H19	120.0
C8—C7—H7B	108.9	C20—C19—H19	120.0
H7A—C7—H7B	107.7	C15—C20—C19	120.88 (17)
C22—C8—C7	108.54 (15)	C15—C20—H20	119.6
C22—C8—C21	109.63 (16)	C19—C20—H20	119.6
C7—C8—C21	110.20 (14)	C8—C21—H21A	109.5
C22—C8—C9	110.41 (15)	C8—C21—H21B	109.5
C7—C8—C9	108.23 (14)	H21A—C21—H21B	109.5
C21—C8—C9	109.80 (15)	C8—C21—H21C	109.5
C10—C9—C8	114.33 (14)	H21A—C21—H21C	109.5
C10—C9—H9A	108.7	H21B—C21—H21C	109.5
C8—C9—H9A	108.7	C8—C22—H22A	109.5
C10—C9—H9B	108.7	C8—C22—H22B	109.5
C8—C9—H9B	108.7	H22A—C22—H22B	109.5
H9A—C9—H9B	107.6	C8—C22—H22C	109.5
O2—C10—C3	120.52 (15)	H22A—C22—H22C	109.5
O2—C10—C9	122.07 (15)	H22B—C22—H22C	109.5
C3—C10—C9	117.34 (15)	C13—C23—H23A	109.5
O3—C11—C5	120.72 (16)	C13—C23—H23B	109.5
O3—C11—C12	121.90 (15)	H23A—C23—H23B	109.5
C5—C11—C12	117.37 (15)	C13—C23—H23C	109.5
C11—C12—C13	114.43 (14)	H23A—C23—H23C	109.5
C11—C12—H12A	108.7	H23B—C23—H23C	109.5
C13—C12—H12A	108.7	C13—C24—H24A	109.5
C11—C12—H12B	108.7	C13—C24—H24B	109.5
C13—C12—H12B	108.7	H24A—C24—H24B	109.5
H12A—C12—H12B	107.6	C13—C24—H24C	109.5
C12—C13—C14	108.04 (14)	H24A—C24—H24C	109.5
C12—C13—C24	109.55 (17)	H24B—C24—H24C	109.5
C14—C13—C24	110.41 (15)	C6—O1—C2	117.81 (11)
C12—C13—C23	109.85 (14)
O1—C2—C3—C10	173.83 (13)	C6—C5—C11—O3	172.63 (16)
C7—C2—C3—C10	−3.8 (2)	C4—C5—C11—O3	−6.6 (2)
O1—C2—C3—C4	−7.5 (2)	C6—C5—C11—C12	−8.5 (2)
C7—C2—C3—C4	174.82 (14)	C4—C5—C11—C12	172.31 (15)
C2—C3—C4—C5	19.19 (19)	O3—C11—C12—C13	−145.42 (19)
C10—C3—C4—C5	−162.15 (13)	C5—C11—C12—C13	35.7 (2)
C2—C3—C4—C15	−104.92 (16)	C11—C12—C13—C14	−53.6 (2)
C10—C3—C4—C15	73.74 (17)	C11—C12—C13—C24	66.7 (2)
C3—C4—C5—C6	−16.4 (2)	C11—C12—C13—C23	−172.93 (18)
C15—C4—C5—C6	106.60 (16)	C5—C6—C14—C13	−23.1 (2)
C3—C4—C5—C11	162.83 (13)	O1—C6—C14—C13	156.85 (14)
C15—C4—C5—C11	−74.21 (18)	C12—C13—C14—C6	46.2 (2)
C11—C5—C6—O1	−177.46 (14)	C24—C13—C14—C6	−73.61 (19)
C4—C5—C6—O1	1.7 (2)	C23—C13—C14—C6	165.75 (16)
C11—C5—C6—C14	2.4 (2)	C3—C4—C15—C20	−125.34 (15)
C4—C5—C6—C14	−178.36 (15)	C5—C4—C15—C20	112.98 (16)
C3—C2—C7—C8	−17.9 (2)	C3—C4—C15—C16	53.10 (19)
O1—C2—C7—C8	164.25 (13)	C5—C4—C15—C16	−68.58 (18)
C2—C7—C8—C22	164.25 (16)	C20—C15—C16—C17	0.9 (2)
C2—C7—C8—C21	−75.68 (18)	C4—C15—C16—C17	−177.63 (15)
C2—C7—C8—C9	44.40 (18)	C15—C16—C17—C18	0.1 (3)
C22—C8—C9—C10	−172.24 (16)	C16—C17—C18—C19	−0.8 (3)
C7—C8—C9—C10	−53.6 (2)	C17—C18—C19—C20	0.6 (3)
C21—C8—C9—C10	66.8 (2)	C16—C15—C20—C19	−1.1 (2)
C2—C3—C10—O2	178.27 (16)	C4—C15—C20—C19	177.38 (16)
C4—C3—C10—O2	−0.4 (2)	C18—C19—C20—C15	0.4 (3)
C2—C3—C10—C9	−4.7 (2)	C5—C6—O1—C2	12.5 (2)
C4—C3—C10—C9	176.63 (14)	C14—C6—O1—C2	−167.45 (13)
C8—C9—C10—O2	−148.28 (17)	C3—C2—O1—C6	−9.5 (2)
C8—C9—C10—C3	34.7 (2)	C7—C2—O1—C6	168.44 (13)