9-(2-Hy-droxy-4,4-dimethyl-6-oxocyclo-hex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetra-hydro-1H-xanthen-1-one.

The cyclo-hexene ring that constitutes a part of the tetra-hydroxanthene fused-ring system of the title compound, C(23)H(26)O(4), adopts a flattened half-chair conformation that approximates an envelope conformation (in which the methyl-ene C atom bearing the two methyl substituents represents the flap) as five of the six atoms lie approximately on a plane (r.m.s. deviation = 0.020 Å). The mean plane of the cyclo-hexene ring with the hy-droxy substituent is approximately perpendicular to the mean plane of the tetra-hydroxanthene system. In the crystal, adjacent mol-ecules are linked by O-H⋯O(carbon-yl) hydrogen bonds into a chain running along the b axis.

Related literature

For the synthesis, see: Pyrko (1996 ▶).

Experimental

Crystal data

C23H26O4

M = 366.44

Orthorhombic,

a = 15.3583 (5) Å

b = 11.3833 (4) Å

c = 22.2070 (7) Å

V = 3882.4 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Bruker SMART APEX diffractometer

40229 measured reflections

4454 independent reflections

3311 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.195

S = 1.03

4454 reflections

251 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.87 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812018934/zs2203sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018934/zs2203Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018934/zs2203Isup3.cml

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

C23H26O4	F(000) = 1568
Mr = 366.44	Dx = 1.254 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7520 reflections
a = 15.3583 (5) Å	θ = 2.3–26.4°
b = 11.3833 (4) Å	µ = 0.09 mm−1
c = 22.2070 (7) Å	T = 293 K
V = 3882.4 (2) Å3	Prism, colorless
Z = 8	0.3 × 0.2 × 0.2 mm

Bruker SMART APEX diffractometer	3311 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
Graphite monochromator	θmax = 27.5°, θmin = 1.8°
φ and ω scans	h = −19→19
40229 measured reflections	k = −14→14
4454 independent reflections	l = −28→28

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0987P)2 + 2.2761P] where P = (Fo2 + 2Fc2)/3
4454 reflections	(Δ/σ)max = 0.001
251 parameters	Δρmax = 0.87 e Å−3
2 restraints	Δρmin = −0.28 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.48195 (10)	0.28998 (14)	0.52034 (7)	0.0505 (4)
O2	0.66264 (11)	−0.01741 (14)	0.45598 (8)	0.0554 (4)
O3	0.70445 (11)	0.32716 (13)	0.44902 (7)	0.0452 (4)
O4	0.59639 (14)	0.0636 (2)	0.30630 (10)	0.0834 (7)
C1	0.46916 (14)	0.33493 (18)	0.46269 (11)	0.0434 (5)
C2	0.41821 (15)	0.4357 (2)	0.45996 (14)	0.0595 (7)
H2	0.3945	0.4680	0.4948	0.071*
C3	0.40360 (17)	0.4863 (2)	0.40516 (16)	0.0677 (8)
H3	0.3701	0.5542	0.4027	0.081*
C4	0.43765 (17)	0.4385 (2)	0.35362 (15)	0.0675 (8)
H4	0.4267	0.4731	0.3165	0.081*
C5	0.48839 (16)	0.3382 (2)	0.35732 (12)	0.0554 (6)
H5	0.5113	0.3057	0.3223	0.067*
C6	0.50576 (13)	0.28513 (18)	0.41254 (10)	0.0410 (5)
C7	0.56366 (13)	0.17701 (16)	0.41671 (9)	0.0366 (4)
H7	0.5317	0.1125	0.3976	0.044*
C8	0.57658 (12)	0.14286 (16)	0.48175 (9)	0.0341 (4)
C9	0.53658 (13)	0.19768 (17)	0.52763 (9)	0.0377 (4)
C10	0.54466 (15)	0.1665 (2)	0.59216 (10)	0.0470 (5)
H10A	0.4980	0.1130	0.6029	0.056*
H10B	0.5381	0.2370	0.6163	0.056*
C11	0.63217 (15)	0.1089 (2)	0.60688 (10)	0.0468 (5)
C12	0.64636 (16)	0.01043 (19)	0.56117 (11)	0.0483 (5)
H12A	0.7057	−0.0178	0.5653	0.058*
H12B	0.6079	−0.0542	0.5713	0.058*
C13	0.63134 (13)	0.04274 (17)	0.49627 (10)	0.0390 (5)
C14	0.6290 (2)	0.0584 (3)	0.67047 (13)	0.0754 (9)
H14A	0.6211	0.1210	0.6989	0.113*
H14B	0.6826	0.0182	0.6789	0.113*
H14C	0.5813	0.0042	0.6736	0.113*
C15	0.70536 (16)	0.1997 (2)	0.60273 (12)	0.0550 (6)
H15A	0.6957	0.2606	0.6319	0.083*
H15B	0.7062	0.2332	0.5631	0.083*
H15C	0.7602	0.1622	0.6106	0.083*
C16	0.64720 (13)	0.19297 (18)	0.38117 (9)	0.0389 (4)
C17	0.71267 (13)	0.26420 (16)	0.39816 (9)	0.0372 (4)
C18	0.79608 (16)	0.2789 (2)	0.36444 (11)	0.0516 (6)
H18A	0.8438	0.2783	0.3930	0.062*
H18B	0.7958	0.3552	0.3450	0.062*
C19	0.81293 (16)	0.1858 (2)	0.31721 (11)	0.0500 (6)
C20	0.7277 (6)	0.168 (3)	0.2842 (3)	0.066 (3)	0.50
H20A	0.7120	0.2404	0.2643	0.079*	0.50
H20B	0.7362	0.1085	0.2533	0.079*	0.50
C20'	0.7318 (6)	0.146 (3)	0.2843 (3)	0.066 (3)	0.50
H20C	0.7179	0.2033	0.2534	0.079*	0.50
H20D	0.7440	0.0721	0.2643	0.079*	0.50
C21	0.65304 (17)	0.1301 (2)	0.32425 (11)	0.0572 (6)
C22	0.8863 (2)	0.2210 (4)	0.27608 (16)	0.0985 (13)
H22A	0.8698	0.2895	0.2536	0.148*
H22B	0.8988	0.1578	0.2488	0.148*
H22C	0.9372	0.2381	0.2996	0.148*
C23	0.8426 (2)	0.0735 (3)	0.35122 (17)	0.0787 (9)
H23A	0.7973	0.0485	0.3781	0.118*
H23B	0.8944	0.0904	0.3739	0.118*
H23C	0.8546	0.0122	0.3227	0.118*
H1	0.751 (2)	0.364 (3)	0.4533 (13)	0.075 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0498 (9)	0.0477 (9)	0.0541 (9)	0.0205 (7)	−0.0029 (7)	−0.0078 (7)
O2	0.0590 (10)	0.0420 (8)	0.0652 (10)	0.0186 (7)	0.0003 (8)	−0.0105 (8)
O3	0.0470 (9)	0.0411 (8)	0.0475 (9)	−0.0143 (7)	0.0084 (7)	−0.0158 (7)
O4	0.0751 (13)	0.1020 (16)	0.0732 (13)	−0.0333 (12)	0.0031 (10)	−0.0475 (12)
C1	0.0348 (10)	0.0341 (10)	0.0612 (13)	0.0025 (8)	−0.0118 (9)	−0.0023 (9)
C2	0.0423 (12)	0.0409 (12)	0.095 (2)	0.0093 (10)	−0.0140 (12)	−0.0044 (12)
C3	0.0469 (14)	0.0409 (12)	0.115 (3)	0.0025 (10)	−0.0264 (15)	0.0163 (15)
C4	0.0495 (14)	0.0624 (16)	0.091 (2)	−0.0052 (12)	−0.0231 (14)	0.0318 (16)
C5	0.0455 (12)	0.0605 (15)	0.0602 (15)	−0.0054 (11)	−0.0149 (11)	0.0113 (12)
C6	0.0310 (9)	0.0352 (10)	0.0569 (13)	−0.0040 (8)	−0.0105 (9)	0.0012 (9)
C7	0.0332 (9)	0.0316 (9)	0.0451 (11)	−0.0046 (8)	−0.0049 (8)	−0.0059 (8)
C8	0.0279 (9)	0.0280 (9)	0.0465 (11)	0.0000 (7)	−0.0009 (7)	−0.0011 (8)
C9	0.0296 (9)	0.0348 (10)	0.0489 (11)	0.0031 (7)	−0.0011 (8)	−0.0025 (8)
C10	0.0452 (12)	0.0503 (13)	0.0455 (12)	0.0032 (9)	0.0048 (9)	−0.0025 (10)
C11	0.0504 (12)	0.0445 (11)	0.0455 (12)	0.0017 (10)	−0.0058 (9)	0.0056 (9)
C12	0.0483 (12)	0.0356 (10)	0.0609 (14)	0.0041 (9)	−0.0060 (10)	0.0069 (10)
C13	0.0327 (9)	0.0296 (9)	0.0547 (12)	0.0007 (8)	−0.0024 (8)	−0.0024 (8)
C14	0.091 (2)	0.0772 (19)	0.0584 (16)	−0.0007 (17)	−0.0129 (15)	0.0207 (14)
C15	0.0500 (13)	0.0497 (13)	0.0653 (15)	0.0015 (10)	−0.0146 (11)	−0.0025 (11)
C16	0.0389 (10)	0.0386 (10)	0.0393 (10)	−0.0028 (8)	−0.0005 (8)	−0.0069 (8)
C17	0.0431 (10)	0.0304 (9)	0.0380 (10)	−0.0038 (8)	0.0038 (8)	−0.0055 (8)
C18	0.0533 (13)	0.0459 (12)	0.0555 (13)	−0.0143 (10)	0.0165 (11)	−0.0131 (10)
C19	0.0489 (12)	0.0559 (13)	0.0451 (12)	−0.0021 (10)	0.0076 (10)	−0.0149 (10)
C20	0.072 (2)	0.078 (9)	0.0491 (14)	−0.002 (3)	0.0043 (13)	−0.0216 (17)
C20'	0.072 (2)	0.078 (9)	0.0491 (14)	−0.002 (3)	0.0043 (13)	−0.0216 (17)
C21	0.0563 (14)	0.0649 (15)	0.0504 (13)	−0.0099 (12)	0.0013 (11)	−0.0213 (12)
C22	0.098 (2)	0.114 (3)	0.084 (2)	−0.041 (2)	0.051 (2)	−0.044 (2)
C23	0.0643 (17)	0.0632 (17)	0.108 (3)	0.0111 (14)	0.0051 (17)	−0.0101 (17)

O1—C9	1.354 (2)	C12—H12A	0.9700
O1—C1	1.393 (3)	C12—H12B	0.9700
O2—C13	1.225 (3)	C14—H14A	0.9600
O3—C17	1.344 (2)	C14—H14B	0.9600
O3—H1	0.83 (3)	C14—H14C	0.9600
O4—C21	1.220 (3)	C15—H15A	0.9600
C1—C6	1.370 (3)	C15—H15B	0.9600
C1—C2	1.390 (3)	C15—H15C	0.9600
C2—C3	1.365 (4)	C16—C17	1.346 (3)
C2—H2	0.9300	C16—C21	1.456 (3)
C3—C4	1.371 (4)	C17—C18	1.493 (3)
C3—H3	0.9300	C18—C19	1.513 (3)
C4—C5	1.384 (4)	C18—H18A	0.9700
C4—H4	0.9300	C18—H18B	0.9700
C5—C6	1.393 (3)	C19—C22	1.505 (4)
C5—H5	0.9300	C19—C20'	1.514 (7)
C6—C7	1.521 (3)	C19—C20	1.514 (7)
C7—C8	1.509 (3)	C19—C23	1.553 (4)
C7—C16	1.517 (3)	C20—C21	1.513 (7)
C7—H7	0.9800	C20—H20A	0.9700
C8—C9	1.344 (3)	C20—H20B	0.9700
C8—C13	1.453 (3)	C20'—C21	1.510 (7)
C9—C10	1.482 (3)	C20'—H20C	0.9700
C10—C11	1.530 (3)	C20'—H20D	0.9700
C10—H10A	0.9700	C22—H22A	0.9600
C10—H10B	0.9700	C22—H22B	0.9600
C11—C14	1.526 (3)	C22—H22C	0.9600
C11—C12	1.528 (3)	C23—H23A	0.9600
C11—C15	1.530 (3)	C23—H23B	0.9600
C12—C13	1.505 (3)	C23—H23C	0.9600
C9—O1—C1	118.84 (17)	H14B—C14—H14C	109.5
C17—O3—H1	107 (2)	C11—C15—H15A	109.5
C6—C1—C2	122.5 (2)	C11—C15—H15B	109.5
C6—C1—O1	122.50 (18)	H15A—C15—H15B	109.5
C2—C1—O1	115.0 (2)	C11—C15—H15C	109.5
C3—C2—C1	118.7 (3)	H15A—C15—H15C	109.5
C3—C2—H2	120.7	H15B—C15—H15C	109.5
C1—C2—H2	120.7	C17—C16—C21	119.59 (19)
C2—C3—C4	120.9 (2)	C17—C16—C7	123.94 (18)
C2—C3—H3	119.5	C21—C16—C7	116.41 (18)
C4—C3—H3	119.5	O3—C17—C16	119.13 (18)
C3—C4—C5	119.5 (3)	O3—C17—C18	116.26 (17)
C3—C4—H4	120.2	C16—C17—C18	124.61 (18)
C5—C4—H4	120.2	C17—C18—C19	114.57 (18)
C4—C5—C6	121.2 (3)	C17—C18—H18A	108.6
C4—C5—H5	119.4	C19—C18—H18A	108.6
C6—C5—H5	119.4	C17—C18—H18B	108.6
C1—C6—C5	117.2 (2)	C19—C18—H18B	108.6
C1—C6—C7	121.67 (19)	H18A—C18—H18B	107.6
C5—C6—C7	121.1 (2)	C22—C19—C18	111.2 (2)
C8—C7—C16	114.67 (16)	C22—C19—C20'	113.8 (3)
C8—C7—C6	110.10 (16)	C18—C19—C20'	113.8 (10)
C16—C7—C6	111.46 (17)	C22—C19—C20	113.0 (4)
C8—C7—H7	106.7	C18—C19—C20	106.4 (10)
C16—C7—H7	106.7	C22—C19—C23	107.1 (3)
C6—C7—H7	106.7	C18—C19—C23	106.8 (2)
C9—C8—C13	117.44 (19)	C20'—C19—C23	103.3 (12)
C9—C8—C7	123.10 (17)	C20—C19—C23	112.2 (12)
C13—C8—C7	119.39 (17)	C21—C20—C19	114.2 (6)
C8—C9—O1	123.57 (19)	C21—C20—H20A	108.7
C8—C9—C10	125.72 (18)	C19—C20—H20A	108.7
O1—C9—C10	110.71 (17)	C21—C20—H20B	108.7
C9—C10—C11	112.51 (18)	C19—C20—H20B	108.7
C9—C10—H10A	109.1	H20A—C20—H20B	107.6
C11—C10—H10A	109.1	C21—C20'—C19	114.3 (6)
C9—C10—H10B	109.1	C21—C20'—H20C	108.7
C11—C10—H10B	109.1	C19—C20'—H20C	108.7
H10A—C10—H10B	107.8	C21—C20'—H20D	108.7
C14—C11—C12	110.0 (2)	C19—C20'—H20D	108.7
C14—C11—C15	109.5 (2)	H20C—C20'—H20D	107.6
C12—C11—C15	110.5 (2)	O4—C21—C16	123.0 (2)
C14—C11—C10	109.3 (2)	O4—C21—C20'	117.0 (7)
C12—C11—C10	107.30 (18)	C16—C21—C20'	120.0 (7)
C15—C11—C10	110.09 (19)	O4—C21—C20	121.6 (6)
C13—C12—C11	115.78 (18)	C16—C21—C20	114.7 (8)
C13—C12—H12A	108.3	C19—C22—H22A	109.5
C11—C12—H12A	108.3	C19—C22—H22B	109.5
C13—C12—H12B	108.3	H22A—C22—H22B	109.5
C11—C12—H12B	108.3	C19—C22—H22C	109.5
H12A—C12—H12B	107.4	H22A—C22—H22C	109.5
O2—C13—C8	120.2 (2)	H22B—C22—H22C	109.5
O2—C13—C12	120.17 (19)	C19—C23—H23A	109.5
C8—C13—C12	119.54 (18)	C19—C23—H23B	109.5
C11—C14—H14A	109.5	H23A—C23—H23B	109.5
C11—C14—H14B	109.5	C19—C23—H23C	109.5
H14A—C14—H14B	109.5	H23A—C23—H23C	109.5
C11—C14—H14C	109.5	H23B—C23—H23C	109.5
H14A—C14—H14C	109.5
C9—O1—C1—C6	3.9 (3)	C7—C8—C13—C12	178.33 (18)
C9—O1—C1—C2	−174.64 (19)	C11—C12—C13—O2	160.3 (2)
C6—C1—C2—C3	0.5 (3)	C11—C12—C13—C8	−22.2 (3)
O1—C1—C2—C3	179.0 (2)	C8—C7—C16—C17	−53.9 (3)
C1—C2—C3—C4	0.6 (4)	C6—C7—C16—C17	72.1 (3)
C2—C3—C4—C5	−0.8 (4)	C8—C7—C16—C21	128.9 (2)
C3—C4—C5—C6	−0.2 (4)	C6—C7—C16—C21	−105.2 (2)
C2—C1—C6—C5	−1.4 (3)	C21—C16—C17—O3	176.1 (2)
O1—C1—C6—C5	−179.84 (19)	C7—C16—C17—O3	−1.0 (3)
C2—C1—C6—C7	178.05 (19)	C21—C16—C17—C18	−4.3 (3)
O1—C1—C6—C7	−0.4 (3)	C7—C16—C17—C18	178.6 (2)
C4—C5—C6—C1	1.2 (3)	O3—C17—C18—C19	165.1 (2)
C4—C5—C6—C7	−178.2 (2)	C16—C17—C18—C19	−14.5 (3)
C1—C6—C7—C8	−3.4 (3)	C17—C18—C19—C22	167.0 (3)
C5—C6—C7—C8	176.07 (18)	C17—C18—C19—C20'	36.9 (10)
C1—C6—C7—C16	−131.8 (2)	C17—C18—C19—C20	43.6 (9)
C5—C6—C7—C16	47.6 (2)	C17—C18—C19—C23	−76.4 (3)
C16—C7—C8—C9	130.8 (2)	C22—C19—C20—C21	178.9 (14)
C6—C7—C8—C9	4.2 (3)	C18—C19—C20—C21	−59 (2)
C16—C7—C8—C13	−52.2 (2)	C20'—C19—C20—C21	82 (3)
C6—C7—C8—C13	−178.86 (16)	C23—C19—C20—C21	58 (2)
C13—C8—C9—O1	−178.15 (18)	C22—C19—C20'—C21	−170.2 (14)
C7—C8—C9—O1	−1.1 (3)	C18—C19—C20'—C21	−41 (2)
C13—C8—C9—C10	1.3 (3)	C20—C19—C20'—C21	−83 (3)
C7—C8—C9—C10	178.28 (19)	C23—C19—C20'—C21	74 (2)
C1—O1—C9—C8	−3.2 (3)	C17—C16—C21—O4	179.5 (3)
C1—O1—C9—C10	177.35 (18)	C7—C16—C21—O4	−3.1 (4)
C8—C9—C10—C11	28.1 (3)	C17—C16—C21—C20'	−0.7 (13)
O1—C9—C10—C11	−152.46 (19)	C7—C16—C21—C20'	176.7 (13)
C9—C10—C11—C14	−169.2 (2)	C17—C16—C21—C20	−9.8 (12)
C9—C10—C11—C12	−49.9 (2)	C7—C16—C21—C20	167.6 (12)
C9—C10—C11—C15	70.5 (3)	C19—C20'—C21—O4	−156.2 (14)
C14—C11—C12—C13	167.1 (2)	C19—C20'—C21—C16	24 (3)
C15—C11—C12—C13	−71.9 (2)	C19—C20'—C21—C20	83 (3)
C10—C11—C12—C13	48.2 (3)	C19—C20—C21—O4	−146.0 (13)
C9—C8—C13—O2	173.0 (2)	C19—C20—C21—C16	43 (2)
C7—C8—C13—O2	−4.2 (3)	C19—C20—C21—C20'	−82 (3)
C9—C8—C13—C12	−4.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O2i	0.83 (3)	1.90 (3)	2.706 (2)	165 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1⋯O2i	0.83 (3)	1.90 (3)	2.706 (2)	165 (3)

Symmetry code: (i) .