9-(2-Hy­droxy-4,4-dimethyl-6-oxocyclo­hex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetra­hydro-1H-xanthen-1-one

Kurbanova, M.M.; Gurbanov, A.V.; Mahmudov, K.T.; Maharramov, A.M.; Ng, S.W.

doi:10.1107/S1600536812018934

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1606

doi:10.1107/S1600536812018934

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9-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one

Malahat M. Kurbanova,^a Atash V. Gurbanov,^a Kamran T. Mahmudov,^a Abel M. Maharramov ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 April 2012; accepted 27 April 2012; online 2 May 2012)

The cyclohexene ring that constitutes a part of the tetrahydroxanthene fused-ring system of the title compound, C₂₃H₂₆O₄, adopts a flattened half-chair conformation that approximates an envelope conformation (in which the methylene 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 cyclohexene ring with the hydroxy substituent is approximately perpendicular to the mean plane of the tetrahydroxanthene system. In the crystal, adjacent molecules are linked by O—H⋯O_carbonyl hydrogen bonds into a chain running along the b axis.

Related literature

For the synthesis, see: Pyrko (1996 ).

Experimental

Crystal data

C₂₃H₂₆O₄
M_r = 366.44
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.062
wR(F²) = 0.195
S = 1.03
4454 reflections
251 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.28 e Å⁻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) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812018934/zs2203sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812018934/zs2203Isup3.cml

checkCIF report

Comment top

Dimedone condenses with an aromatic aldehyde such an salicylaldehyde to yield aldimedone, the reaction often being used as a method for characterizing aromatic aldehydes. Aldimedone is then dehydrated to the title compound C₂₃H₂₆O₄ (Scheme I), which features a pyran ring (Pyrko, 1996). The cyclohexene ring that constitutes a part of the tetrahydroxanthene fused-ring system has a flattened half-chair conformation that approximates an envelope conformation (in which the methylene C atom bearing the dimethyl substituent represents the flap) as five of the six atoms lie on a plane (Fig. 1). The mean plane of the cyclohexene ring with the hydroxy substituent is approximately perpendicular to the mean plane of the tetrahydroxanthene system. Adjacent molecules are linked by an O–H···O_carbonyl hydrogen bond to form a chain (Fig. 2, Table 1), running along the b-axis of the orthorhombic unit cell.

Related literature top

For the synthesis, see: Pyrko (1996).

Experimental top

The compound was synthesized by using a literature method (Pyrko, 1996) and ethanol was used as the recrystallization solvent.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₃H₂₆O₄ at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
	Fig. 2. The hydrogen-bonded chain motif showing hydrogen bonds as dashed lines..

9-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9- tetrahydro-1H-xanthen-1-one top

Crystal data top

C₂₃H₂₆O₄	F(000) = 1568
M_r = 366.44	D_x = 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

Data collection top

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

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)] = 0.062	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(F_o²) + (0.0987P)² + 2.2761P] where P = (F_o² + 2F_c²)/3
4454 reflections	(Δ/σ)_max = 0.001
251 parameters	Δρ_max = 0.87 e Å⁻³
2 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₃H₂₆O₄	V = 3882.4 (2) Å³
M_r = 366.44	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.3583 (5) Å	µ = 0.09 mm⁻¹
b = 11.3833 (4) Å	T = 293 K
c = 22.2070 (7) Å	0.3 × 0.2 × 0.2 mm

Data collection top

Bruker SMART APEX diffractometer	3311 reflections with I > 2σ(I)
40229 measured reflections	R_int = 0.035
4454 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	2 restraints
wR(F²) = 0.195	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.87 e Å⁻³
4454 reflections	Δρ_min = −0.28 e Å⁻³
251 parameters

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

	x	y	z	U_iso*/U_eq	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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₆O₄
M_r	366.44
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	15.3583 (5), 11.3833 (4), 22.2070 (7)
V (Å³)	3882.4 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	40229, 4454, 3311
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.195, 1.03
No. of reflections	4454
No. of parameters	251
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.28

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y+1/2, z.

Acknowledgements

We thank Baku State University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Pyrko, A. N. (1996). Chem. Heterocycl. Compd, 32, 635–645. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1606

doi:10.1107/S1600536812018934

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

9-(2-Hy­dr­oxy-4,4-di­methyl-6-oxo­cyclo­hex-1-en-1-yl)-3,3-di­methyl-2,3,4,9-tetra­hydro-1H-xanthen-1-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

9-(2-Hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one