9-(4-Hy­droxy-3,5-dimeth­oxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6,7,9-hexa­hydro-1H-xanthene-1,8(2H)-dione

Sughanya, V.; Sureshbabu, N.

doi:10.1107/S1600536812010410

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1060

doi:10.1107/S1600536812010410

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9-(4-Hydroxy-3,5-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

V. Sughanya ^a ^* and N. Sureshbabu ^a

^aDepartment of Chemistry, Annamalai University, Annamalai nagar 608 002, Tamil Nadu, India
^*Correspondence e-mail: saisukanyashri@gmail.com

(Received 27 January 2012; accepted 8 March 2012; online 14 March 2012)

In the title compound, C₂₅H₃₀O₆, the two fused cyclohexanone rings have envelope conformations, whereas the central pyran ring is roughly planar [mximum deviation = 0.045 (2) Å]. The pyran and benzene rings are almost perpendicular to each other, making a dihedral angle of 86.32 (2)°. In the crystal, molecules are linked via pairs of O—H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For the synthesis of xanthenes, see: Vang & Stankevich (1960 ); Hilderbrand & Weissleder (2007 ). For their pharmaceutical properties, see: Lambert et al. (1997 ); Poupelin et al. (1978 ); Hideo (1981 ); Selvanayagam et al. (1996 ); Jonathan et al. (1988 ). For related structures, see Mehdi et al. (2011 ); Odabasoglu et al. (2008 ). For the assignment of ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₅H₃₀O₆
M_r = 426.49
Triclinic, $[P \overline 1]$
a = 9.4268 (9) Å
b = 10.2468 (10) Å
c = 12.6122 (11) Å
α = 84.973 (6)°
β = 70.377 (5)°
γ = 75.676 (6)°
V = 1111.83 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.924, T_max = 0.982
20849 measured reflections
5233 independent reflections
2876 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.157
S = 0.98
5233 reflections
288 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O2ⁱ	0.82	2.02	2.762 (2)	151
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812010410/im2356sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010410/im2356Isup5.hkl

Supporting information file. DOI: 10.1107/S1600536812010410/im2356Isup3.cml

checkCIF report

Comment top

Xanthene is the parent compound of a number of naturally occurring substances and some synthetic dyes. Xanthene derivatives are used as dyes (Hilderbrand & Weissleder, 2007) and they possess biological properties like antibacterial, antiviral, anti-inflammatory (Jonathan et al., 1988) activities and are therefore used in medicine. Ehretianone, a quinonoid xanthene was reported to possess antisnake venom activity (Selvanayagam et al., 1996; Lambert et al., 1997; Poupelin et al., 1978; Hideo, 1981).

In the title compound (I), the cyclohexenone rings C1–C6 and C8–C13 both adopt an envelope conformation. In contrast, the pyran ring (O1/C1/C6/C8/C13) is almost planar with a slight deviation of C7 (0.99 Å) from the (C8/C13/O1/C1/C6) plane. The pyran ring and phenyl ring are almost perpendicular to one another making a dihedral angle of 86.32 (2)°. The bond lengths and angles are consistent with the reported structure (Odabasoglu et al., 2008; Mehdi et al., 2011). In the crystal structure, a relatively short intermolecular O5—H5···O2 hydrogen bond leads to the observation of centrosymmetrical dimers.

Related literature top

For the synthesis of xanthenes, see: Vang & Stankevich (1960); Hilderbrand & Weissleder (2007). For their pharmaceutical properties, see: Lambert et al. (1997); Poupelin et al. (1978); Hideo (1981); Selvanayagam et al. (1996); Jonathan et al. (1988). For related structures, see Mehdi et al. (2011); Odabasoglu et al. (2008). For the assignment of ring conformations, see: Cremer & Pople (1975).

Experimental top

The title compound was prepared in two stages (Vang & Stankevich, 1960). In the first stage, a mixture of 4-hydroxy-3,5-dimethoxybenzaldehyde (0.5 g, 8 m mol), 5,5-dimethylcyclohexane-1,3-dione (1.15 g, 1.6 mmol) and 10 ml of ethanol was heated to 70°C for about 10 minutes. The reaction mixture was allowed to cool to room temperature and the resulting solid intermediate 2,2'-((4-hydroxy-3,5-dimethoxyphenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) was filtered and dried. In the second stage, about 0.5 g of this intermediate were dissolved in 25 ml of ethanol. The content was refluxed together with 15 drops of concentrated hydrochloric acid for 30 minutes with the reaction being monitored by TLC. After completion of the reaction, the reaction mixture was poured into crushed ice and stirred well. The solid separated was filtered, dried and then recrystallized from ethanol to yield colourless crystals of t he title compound (m.p. 490–492 K; yield: 85%).

Structure description top

For the synthesis of xanthenes, see: Vang & Stankevich (1960); Hilderbrand & Weissleder (2007). For their pharmaceutical properties, see: Lambert et al. (1997); Poupelin et al. (1978); Hideo (1981); Selvanayagam et al. (1996); Jonathan et al. (1988). For related structures, see Mehdi et al. (2011); Odabasoglu et al. (2008). For the assignment of ring conformations, see: Cremer & Pople (1975).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. : Molecular structure of (I), showing displacement ellipsoids at the 30% probability level.
	Fig. 2. : Packing diagram for (I) showing the formation of O—H···O hydrogen bonds between the molecules in the unit cell.

9-(4-Hydroxy-3,5-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9- hexahydro-1H-xanthene-1,8(2H)-dione top

Crystal data top

C₂₅H₃₀O₆	Z = 2
M_r = 426.49	F(000) = 456
Triclinic, P1	D_x = 1.274 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4268 (9) Å	Cell parameters from 5637 reflections
b = 10.2468 (10) Å	θ = 2.4–27.5°
c = 12.6122 (11) Å	µ = 0.09 mm⁻¹
α = 84.973 (6)°	T = 295 K
β = 70.377 (5)°	Block, colourless
γ = 75.676 (6)°	0.30 × 0.25 × 0.20 mm
V = 1111.83 (18) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	5233 independent reflections
Radiation source: fine-focus sealed tube	2876 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ω and φ scan	θ_max = 28.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
T_min = 0.924, T_max = 0.982	k = −13→13
20849 measured reflections	l = −16→16

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)] = 0.051	H-atom parameters constrained
wR(F²) = 0.157	w = 1/[σ²(F_o²) + (0.0666P)² + 0.3374P] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
5233 reflections	Δρ_max = 0.28 e Å⁻³
288 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.008 (2)

Crystal data top

C₂₅H₃₀O₆	γ = 75.676 (6)°
M_r = 426.49	V = 1111.83 (18) Å³
Triclinic, P1	Z = 2
a = 9.4268 (9) Å	Mo Kα radiation
b = 10.2468 (10) Å	µ = 0.09 mm⁻¹
c = 12.6122 (11) Å	T = 295 K
α = 84.973 (6)°	0.30 × 0.25 × 0.20 mm
β = 70.377 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5233 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2876 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.982	R_int = 0.052
20849 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 0.98	Δρ_max = 0.28 e Å⁻³
5233 reflections	Δρ_min = −0.21 e Å⁻³
288 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
C1	0.2424 (2)	0.1023 (2)	0.33354 (14)	0.0336 (5)
C2	0.1297 (3)	0.0482 (2)	0.30200 (15)	0.0418 (5)
H2A	0.0310	0.0657	0.3621	0.050*
H2B	0.1666	−0.0486	0.2923	0.050*
C3	0.1076 (3)	0.1131 (2)	0.19256 (16)	0.0466 (6)
C4	0.2682 (3)	0.0985 (3)	0.10508 (16)	0.0509 (6)
H4A	0.3068	0.0052	0.0814	0.061*
H4B	0.2577	0.1524	0.0398	0.061*
C5	0.3873 (2)	0.1383 (2)	0.14149 (15)	0.0381 (5)
C6	0.3614 (2)	0.1462 (2)	0.26230 (14)	0.0337 (5)
C7	0.4681 (2)	0.2063 (2)	0.29943 (14)	0.0354 (5)
H7	0.5748	0.1561	0.2636	0.042*
C8	0.4297 (2)	0.1905 (2)	0.42567 (15)	0.0367 (5)
C9	0.5320 (3)	0.2232 (2)	0.47906 (17)	0.0471 (6)
C10	0.4874 (3)	0.2148 (3)	0.60591 (17)	0.0525 (6)
H10A	0.5232	0.2833	0.6315	0.063*
H10B	0.5411	0.1279	0.6263	0.063*
C11	0.3143 (3)	0.2328 (2)	0.66833 (16)	0.0451 (6)
C12	0.2551 (3)	0.1381 (2)	0.61580 (15)	0.0427 (5)
H12A	0.2915	0.0464	0.6383	0.051*
H12B	0.1429	0.1598	0.6446	0.051*
C13	0.3068 (2)	0.1463 (2)	0.49008 (14)	0.0349 (5)
C14	0.0234 (3)	0.2601 (3)	0.2129 (2)	0.0638 (7)
H14A	0.0834	0.3068	0.2375	0.096*
H14B	−0.0758	0.2663	0.2698	0.096*
H14C	0.0094	0.3002	0.1443	0.096*
C15	0.0135 (4)	0.0391 (3)	0.1523 (2)	0.0787 (9)
H15A	−0.0879	0.0488	0.2070	0.118*
H15B	0.0644	−0.0547	0.1429	0.118*
H15C	0.0047	0.0765	0.0817	0.118*
C16	0.2298 (3)	0.3783 (3)	0.6599 (2)	0.0667 (7)
H16A	0.2408	0.4010	0.5825	0.100*
H16B	0.2731	0.4365	0.6893	0.100*
H16C	0.1220	0.3895	0.7026	0.100*
C17	0.2863 (3)	0.1950 (3)	0.79273 (17)	0.0620 (7)
H17A	0.3218	0.2549	0.8271	0.093*
H17B	0.3419	0.1041	0.7987	0.093*
H17C	0.1776	0.2025	0.8303	0.093*
C19	0.4554 (2)	0.3532 (2)	0.26216 (15)	0.0356 (5)
C20	0.5677 (2)	0.3897 (2)	0.16956 (15)	0.0386 (5)
H20	0.6574	0.3259	0.1343	0.046*
C21	0.5475 (2)	0.5199 (2)	0.12944 (15)	0.0395 (5)
C22	0.4165 (2)	0.6183 (2)	0.18321 (16)	0.0401 (5)
C23	0.3081 (2)	0.5825 (2)	0.27940 (16)	0.0401 (5)
C24	0.3262 (2)	0.4511 (2)	0.31724 (15)	0.0402 (5)
H24	0.2510	0.4279	0.3804	0.048*
C25	0.7846 (3)	0.4710 (3)	−0.02256 (19)	0.0637 (7)
H25A	0.8480	0.4413	0.0246	0.096*
H25B	0.8412	0.5123	−0.0894	0.096*
H25C	0.7565	0.3952	−0.0428	0.096*
C26	0.1124 (3)	0.6717 (3)	0.44614 (19)	0.0619 (7)
H26A	0.0458	0.6106	0.4588	0.093*
H26B	0.0524	0.7580	0.4775	0.093*
H26C	0.1899	0.6371	0.4815	0.093*
O1	0.21042 (15)	0.10108 (15)	0.44842 (10)	0.0387 (4)
O2	0.50511 (17)	0.16061 (16)	0.07249 (11)	0.0510 (4)
O3	0.6537 (2)	0.2498 (2)	0.42231 (14)	0.0770 (6)
O4	0.18392 (19)	0.68547 (17)	0.33083 (12)	0.0575 (5)
O5	0.39109 (19)	0.74774 (16)	0.14607 (12)	0.0555 (5)
H5	0.4487	0.7521	0.0813	0.073 (9)*
O6	0.64868 (18)	0.56614 (16)	0.03654 (12)	0.0530 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0421 (11)	0.0337 (13)	0.0199 (9)	−0.0064 (9)	−0.0053 (8)	0.0003 (7)
C2	0.0538 (13)	0.0461 (15)	0.0271 (10)	−0.0215 (11)	−0.0090 (9)	0.0029 (9)
C3	0.0586 (14)	0.0583 (17)	0.0297 (11)	−0.0259 (13)	−0.0163 (10)	0.0083 (9)
C4	0.0692 (15)	0.0593 (17)	0.0239 (10)	−0.0193 (13)	−0.0115 (10)	−0.0005 (9)
C5	0.0487 (12)	0.0331 (13)	0.0237 (9)	−0.0060 (10)	−0.0028 (9)	−0.0005 (8)
C6	0.0393 (11)	0.0327 (12)	0.0232 (9)	−0.0061 (9)	−0.0047 (8)	0.0018 (7)
C7	0.0339 (10)	0.0413 (13)	0.0235 (9)	−0.0062 (9)	−0.0024 (8)	0.0024 (8)
C8	0.0402 (11)	0.0398 (14)	0.0252 (9)	−0.0066 (10)	−0.0068 (8)	0.0025 (8)
C9	0.0458 (13)	0.0583 (17)	0.0372 (11)	−0.0162 (12)	−0.0113 (10)	0.0029 (10)
C10	0.0585 (14)	0.0681 (18)	0.0382 (12)	−0.0219 (13)	−0.0209 (11)	0.0044 (10)
C11	0.0577 (14)	0.0515 (16)	0.0275 (10)	−0.0153 (12)	−0.0139 (9)	0.0006 (9)
C12	0.0507 (13)	0.0514 (15)	0.0238 (9)	−0.0152 (11)	−0.0083 (9)	0.0050 (9)
C13	0.0396 (11)	0.0395 (13)	0.0230 (9)	−0.0082 (9)	−0.0081 (8)	0.0028 (8)
C14	0.0564 (15)	0.067 (2)	0.0646 (16)	−0.0124 (14)	−0.0213 (13)	0.0180 (13)
C15	0.103 (2)	0.117 (3)	0.0458 (14)	−0.067 (2)	−0.0367 (15)	0.0168 (14)
C16	0.0893 (19)	0.054 (2)	0.0497 (14)	−0.0081 (15)	−0.0184 (13)	−0.0075 (12)
C17	0.0836 (18)	0.080 (2)	0.0302 (11)	−0.0318 (16)	−0.0193 (12)	0.0020 (11)
C19	0.0387 (11)	0.0428 (14)	0.0248 (9)	−0.0140 (10)	−0.0070 (8)	0.0025 (8)
C20	0.0378 (11)	0.0470 (15)	0.0287 (10)	−0.0140 (10)	−0.0055 (8)	0.0012 (9)
C21	0.0462 (12)	0.0481 (15)	0.0247 (10)	−0.0206 (11)	−0.0064 (9)	0.0047 (9)
C22	0.0519 (13)	0.0386 (14)	0.0315 (10)	−0.0147 (11)	−0.0140 (9)	0.0054 (9)
C23	0.0441 (12)	0.0416 (15)	0.0308 (10)	−0.0077 (10)	−0.0088 (9)	−0.0005 (9)
C24	0.0423 (12)	0.0449 (15)	0.0264 (10)	−0.0136 (10)	−0.0009 (8)	0.0045 (8)
C25	0.0559 (15)	0.077 (2)	0.0435 (13)	−0.0255 (14)	0.0073 (11)	0.0093 (12)
C26	0.0513 (14)	0.066 (2)	0.0489 (14)	0.0000 (13)	0.0002 (11)	−0.0063 (12)
O1	0.0433 (8)	0.0533 (10)	0.0188 (6)	−0.0185 (7)	−0.0048 (6)	0.0037 (6)
O2	0.0561 (9)	0.0598 (12)	0.0250 (7)	−0.0165 (8)	0.0044 (7)	0.0004 (6)
O3	0.0588 (11)	0.1335 (19)	0.0502 (10)	−0.0510 (12)	−0.0144 (9)	0.0094 (10)
O4	0.0634 (10)	0.0447 (11)	0.0443 (9)	0.0036 (8)	−0.0047 (8)	0.0056 (7)
O5	0.0733 (11)	0.0444 (11)	0.0366 (9)	−0.0133 (9)	−0.0053 (8)	0.0110 (7)
O6	0.0582 (10)	0.0533 (11)	0.0370 (8)	−0.0234 (8)	0.0034 (7)	0.0084 (7)

Geometric parameters (Å, º) top

C1—C6	1.330 (2)	C14—H14A	0.9600
C1—O1	1.377 (2)	C14—H14B	0.9600
C1—C2	1.486 (3)	C14—H14C	0.9600
C2—C3	1.534 (3)	C15—H15A	0.9600
C2—H2A	0.9700	C15—H15B	0.9600
C2—H2B	0.9700	C15—H15C	0.9600
C3—C14	1.518 (3)	C16—H16A	0.9600
C3—C15	1.524 (3)	C16—H16B	0.9600
C3—C4	1.525 (3)	C16—H16C	0.9600
C4—C5	1.498 (3)	C17—H17A	0.9600
C4—H4A	0.9700	C17—H17B	0.9600
C4—H4B	0.9700	C17—H17C	0.9600
C5—O2	1.218 (2)	C19—C20	1.383 (2)
C5—C6	1.466 (2)	C19—C24	1.386 (3)
C6—C7	1.511 (3)	C20—C21	1.376 (3)
C7—C8	1.513 (2)	C20—H20	0.9300
C7—C19	1.525 (3)	C21—O6	1.373 (2)
C7—H7	0.9800	C21—C22	1.394 (3)
C8—C13	1.331 (3)	C22—O5	1.358 (2)
C8—C9	1.460 (3)	C22—C23	1.388 (3)
C9—O3	1.213 (2)	C23—C24	1.378 (3)
C9—C10	1.512 (3)	C23—O4	1.379 (3)
C10—C11	1.527 (3)	C24—H24	0.9300
C10—H10A	0.9700	C25—O6	1.419 (3)
C10—H10B	0.9700	C25—H25A	0.9600
C11—C16	1.520 (3)	C25—H25B	0.9600
C11—C12	1.523 (3)	C25—H25C	0.9600
C11—C17	1.532 (3)	C26—O4	1.394 (3)
C12—C13	1.495 (2)	C26—H26A	0.9600
C12—H12A	0.9700	C26—H26B	0.9600
C12—H12B	0.9700	C26—H26C	0.9600
C13—O1	1.374 (2)	O5—H5	0.8200

C6—C1—O1	122.65 (17)	O1—C13—C12	110.98 (15)
C6—C1—C2	125.82 (16)	C3—C14—H14A	109.5
O1—C1—C2	111.53 (15)	C3—C14—H14B	109.5
C1—C2—C3	111.07 (16)	H14A—C14—H14B	109.5
C1—C2—H2A	109.4	C3—C14—H14C	109.5
C3—C2—H2A	109.4	H14A—C14—H14C	109.5
C1—C2—H2B	109.4	H14B—C14—H14C	109.5
C3—C2—H2B	109.4	C3—C15—H15A	109.5
H2A—C2—H2B	108.0	C3—C15—H15B	109.5
C14—C3—C15	109.6 (2)	H15A—C15—H15B	109.5
C14—C3—C4	111.30 (18)	C3—C15—H15C	109.5
C15—C3—C4	109.35 (19)	H15A—C15—H15C	109.5
C14—C3—C2	109.76 (18)	H15B—C15—H15C	109.5
C15—C3—C2	109.56 (18)	C11—C16—H16A	109.5
C4—C3—C2	107.25 (18)	C11—C16—H16B	109.5
C5—C4—C3	116.38 (16)	H16A—C16—H16B	109.5
C5—C4—H4A	108.2	C11—C16—H16C	109.5
C3—C4—H4A	108.2	H16A—C16—H16C	109.5
C5—C4—H4B	108.2	H16B—C16—H16C	109.5
C3—C4—H4B	108.2	C11—C17—H17A	109.5
H4A—C4—H4B	107.3	C11—C17—H17B	109.5
O2—C5—C6	120.52 (19)	H17A—C17—H17B	109.5
O2—C5—C4	120.89 (17)	C11—C17—H17C	109.5
C6—C5—C4	118.57 (17)	H17A—C17—H17C	109.5
C1—C6—C5	117.83 (18)	H17B—C17—H17C	109.5
C1—C6—C7	123.52 (16)	C20—C19—C24	119.02 (19)
C5—C6—C7	118.64 (16)	C20—C19—C7	120.75 (18)
C6—C7—C8	109.05 (15)	C24—C19—C7	120.14 (16)
C6—C7—C19	110.37 (15)	C21—C20—C19	120.34 (19)
C8—C7—C19	112.14 (16)	C21—C20—H20	119.8
C6—C7—H7	108.4	C19—C20—H20	119.8
C8—C7—H7	108.4	O6—C21—C20	125.29 (19)
C19—C7—H7	108.4	O6—C21—C22	113.83 (19)
C13—C8—C9	118.53 (17)	C20—C21—C22	120.88 (18)
C13—C8—C7	122.46 (18)	O5—C22—C23	118.68 (19)
C9—C8—C7	119.01 (17)	O5—C22—C21	122.90 (18)
O3—C9—C8	120.50 (19)	C23—C22—C21	118.42 (19)
O3—C9—C10	120.9 (2)	C24—C23—O4	123.88 (18)
C8—C9—C10	118.48 (18)	C24—C23—C22	120.51 (19)
C9—C10—C11	115.06 (18)	O4—C23—C22	115.60 (19)
C9—C10—H10A	108.5	C23—C24—C19	120.71 (18)
C11—C10—H10A	108.5	C23—C24—H24	119.6
C9—C10—H10B	108.5	C19—C24—H24	119.6
C11—C10—H10B	108.5	O6—C25—H25A	109.5
H10A—C10—H10B	107.5	O6—C25—H25B	109.5
C16—C11—C12	110.94 (19)	H25A—C25—H25B	109.5
C16—C11—C10	110.21 (19)	O6—C25—H25C	109.5
C12—C11—C10	107.87 (18)	H25A—C25—H25C	109.5
C16—C11—C17	108.95 (19)	H25B—C25—H25C	109.5
C12—C11—C17	108.65 (18)	O4—C26—H26A	109.5
C10—C11—C17	110.20 (19)	O4—C26—H26B	109.5
C13—C12—C11	112.93 (17)	H26A—C26—H26B	109.5
C13—C12—H12A	109.0	O4—C26—H26C	109.5
C11—C12—H12A	109.0	H26A—C26—H26C	109.5
C13—C12—H12B	109.0	H26B—C26—H26C	109.5
C11—C12—H12B	109.0	C13—O1—C1	118.10 (14)
H12A—C12—H12B	107.8	C23—O4—C26	116.45 (17)
C8—C13—O1	123.71 (16)	C22—O5—H5	109.5
C8—C13—C12	125.31 (18)	C21—O6—C25	116.86 (18)

C6—C1—C2—C3	−30.4 (3)	C10—C11—C12—C13	−48.2 (2)
O1—C1—C2—C3	150.19 (18)	C17—C11—C12—C13	−167.64 (19)
C1—C2—C3—C14	−69.1 (2)	C9—C8—C13—O1	−173.90 (19)
C1—C2—C3—C15	170.5 (2)	C7—C8—C13—O1	5.3 (3)
C1—C2—C3—C4	51.9 (2)	C9—C8—C13—C12	5.7 (3)
C14—C3—C4—C5	71.9 (2)	C7—C8—C13—C12	−175.1 (2)
C15—C3—C4—C5	−166.9 (2)	C11—C12—C13—C8	22.5 (3)
C2—C3—C4—C5	−48.2 (3)	C11—C12—C13—O1	−157.83 (18)
C3—C4—C5—O2	−162.6 (2)	C6—C7—C19—C20	−102.2 (2)
C3—C4—C5—C6	19.2 (3)	C8—C7—C19—C20	136.03 (18)
O1—C1—C6—C5	177.92 (18)	C6—C7—C19—C24	74.3 (2)
C2—C1—C6—C5	−1.4 (3)	C8—C7—C19—C24	−47.5 (2)
O1—C1—C6—C7	−3.6 (3)	C24—C19—C20—C21	−3.3 (3)
C2—C1—C6—C7	177.01 (19)	C7—C19—C20—C21	173.18 (18)
O2—C5—C6—C1	−170.53 (19)	C19—C20—C21—O6	−177.93 (18)
C4—C5—C6—C1	7.7 (3)	C19—C20—C21—C22	2.2 (3)
O2—C5—C6—C7	11.0 (3)	O6—C21—C22—O5	0.7 (3)
C4—C5—C6—C7	−170.83 (19)	C20—C21—C22—O5	−179.44 (18)
C1—C6—C7—C8	7.4 (3)	O6—C21—C22—C23	−178.83 (17)
C5—C6—C7—C8	−174.20 (17)	C20—C21—C22—C23	1.1 (3)
C1—C6—C7—C19	−116.2 (2)	O5—C22—C23—C24	177.31 (19)
C5—C6—C7—C19	62.2 (2)	C21—C22—C23—C24	−3.2 (3)
C6—C7—C8—C13	−8.1 (3)	O5—C22—C23—O4	−1.7 (3)
C19—C7—C8—C13	114.5 (2)	C21—C22—C23—O4	177.83 (18)
C6—C7—C8—C9	171.07 (18)	O4—C23—C24—C19	−179.03 (18)
C19—C7—C8—C9	−66.4 (2)	C22—C23—C24—C19	2.1 (3)
C13—C8—C9—O3	172.1 (2)	C20—C19—C24—C23	1.2 (3)
C7—C8—C9—O3	−7.1 (3)	C7—C19—C24—C23	−175.31 (18)
C13—C8—C9—C10	−4.4 (3)	C8—C13—O1—C1	−0.4 (3)
C7—C8—C9—C10	176.45 (19)	C12—C13—O1—C1	179.94 (16)
O3—C9—C10—C11	158.3 (2)	C6—C1—O1—C13	−0.5 (3)
C8—C9—C10—C11	−25.3 (3)	C2—C1—O1—C13	178.95 (17)
C9—C10—C11—C16	−70.9 (3)	C24—C23—O4—C26	27.8 (3)
C9—C10—C11—C12	50.4 (3)	C22—C23—O4—C26	−153.2 (2)
C9—C10—C11—C17	168.8 (2)	C20—C21—O6—C25	0.3 (3)
C16—C11—C12—C13	72.6 (2)	C22—C21—O6—C25	−179.86 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2ⁱ	0.82	2.02	2.762 (2)	151

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₅H₃₀O₆
M_r	426.49
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.4268 (9), 10.2468 (10), 12.6122 (11)
α, β, γ (°)	84.973 (6), 70.377 (5), 75.676 (6)
V (Å³)	1111.83 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.924, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	20849, 5233, 2876
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.157, 0.98
No. of reflections	5233
No. of parameters	288
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.21

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2ⁱ	0.82	2.02	2.762 (2)	150.6

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

The authors thank Dr Babu Varghese and the SAIF, IIT Madras, for the intensity data collection

References

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

9-(4-Hy­dr­oxy-3,5-dimeth­­oxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6,7,9-hexa­hydro-1H-xanthene-1,8(2H)-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

9-(4-Hydroxy-3,5-dimethoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione