12-(2-Methoxyphenyl)-9,9-dimethyl-8,9-dihydro-12H-benzo[a]xanthen-11(10H)-one

Li, D.-L.; Wang, L.-H.

doi:10.1107/S1600536809052210

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o119

doi:10.1107/S1600536809052210

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12-(2-Methoxyphenyl)-9,9-dimethyl-8,9-dihydro-12H-benzo[a]xanthen-11(10H)-one

De-Ling Li ^a ^* and Li-Hong Wang ^a

^aDepartment of Chemistry, Tangshan Normal College, Tangshan 063000, People's Republic of China
^*Correspondence e-mail: deling1@126.com

(Received 6 November 2009; accepted 4 December 2009; online 12 December 2009)

The title compound, C₂₆H₂₄O₃, was synthesized via the coupling of 2-methoxybenzaldehyde, 2-naphthol and 5,5-dimethylcyclohexane-1,3-dione. The pyran ring adopts a boat conformation, while the cyclohexenone ring is in an envelope conformation. The 2-methoxyphenyl ring is almost perpendicular to the plane through the four C atoms of the pyran ring [dihedral angle = 88.76 (9)°].

Related literature

For the antiviral activity of xanthenes and benzoxanthenes, see: Lambert et al. (1997 ).

Experimental

Crystal data

C₂₆H₂₄O₃
M_r = 384.45
Monoclinic, P 2₁ /n
a = 7.8454 (11) Å
b = 22.670 (3) Å
c = 11.3100 (13) Å
β = 98.893 (4)°
V = 1987.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 K
0.36 × 0.28 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.970, T_max = 0.985
12038 measured reflections
3860 independent reflections
3274 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.122
S = 1.09
3860 reflections
266 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052210/nc2168sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052210/nc2168Isup2.hkl

checkCIF report

Related literature top

For the antiviral activity of xanthenes and benzoxanthenes, see: (Lambert et al. (1997).

Experimental top

To a mixture of 2-naphthol (1.0 mmol), 2-methoxybenzaldehyde (1.0 mmol), and 5,5-dimethylcyclohexane-1,3-dione (1.1 mmol) strontium trifluoromethanesulfonate (0.1 mmol) in 1,2-dichloroethane (2 ml) was added. The mixture was stirred at 80 °C for 5 h and the progress of the reaction was monitored by thin layer chromatography. After completion of the reaction, 5 ml of water were added and the product was extracted three times with 10 ml of ethyl acetate. The organic layer was dried over MgSO₄ filtered off and the solvent was evaporated. The crude was product dissolved in ethylacetate and purified by flash chromatography on silica gel. The solvent was evaporated and the product was dissolved in ethanol. A single crystal was obtained by slow evaporation of the solvent from a solution in ethanol.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecular structure of (I), showing the atom-numbering scheme. Dispacement ellipsoids are drawn at the 30% probability level.

12-(2-Methoxyphenyl)-9,9-dimethyl-9,10-dihydro-8H- benzo[a]xanthen-11(12H)-one top

Crystal data top

C₂₆H₂₄O₃	F(000) = 816
M_r = 384.45	D_x = 1.285 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71070 Å
a = 7.8454 (11) Å	Cell parameters from 3867 reflections
b = 22.670 (3) Å	θ = 1.8–27.2°
c = 11.3100 (13) Å	µ = 0.08 mm⁻¹
β = 98.893 (4)°	T = 113 K
V = 1987.4 (5) Å³	Block, colorless
Z = 4	0.36 × 0.28 × 0.20 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3860 independent reflections
Radiation source: rotating anode	3274 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.035
Detector resolution: 7.31 pixels mm^-1	θ_max = 26.0°, θ_min = 2.0°
ω and ϕ scans	h = −9→8
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −27→20
T_min = 0.970, T_max = 0.985	l = −13→13
12038 measured reflections

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-atom parameters constrained
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0629P)² + 0.2114P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
3860 reflections	Δρ_max = 0.29 e Å⁻³
266 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (2)

Crystal data top

C₂₆H₂₄O₃	V = 1987.4 (5) Å³
M_r = 384.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8454 (11) Å	µ = 0.08 mm⁻¹
b = 22.670 (3) Å	T = 113 K
c = 11.3100 (13) Å	0.36 × 0.28 × 0.20 mm
β = 98.893 (4)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3860 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	3274 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.985	R_int = 0.035
12038 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.09	Δρ_max = 0.29 e Å⁻³
3860 reflections	Δρ_min = −0.21 e Å⁻³
266 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	0.32998 (13)	0.05276 (4)	0.89201 (9)	0.0251 (3)
O2	−0.07739 (15)	0.20650 (5)	0.81569 (13)	0.0444 (4)
O3	0.19539 (13)	0.05495 (5)	0.63209 (9)	0.0249 (3)
C1	0.2801 (2)	0.11049 (7)	0.87702 (13)	0.0239 (4)
C2	0.11615 (19)	0.12678 (7)	0.84090 (13)	0.0237 (4)
C3	−0.0248 (2)	0.08279 (6)	0.79729 (13)	0.0226 (3)
H3	−0.1274	0.0930	0.8358	0.027*
C4	0.03259 (19)	0.02110 (7)	0.83795 (12)	0.0220 (3)
C5	0.20193 (19)	0.00984 (7)	0.88233 (12)	0.0229 (3)
C6	0.2635 (2)	−0.04641 (7)	0.92099 (13)	0.0259 (4)
H6	0.3813	−0.0518	0.9543	0.031*
C7	0.1525 (2)	−0.09314 (7)	0.91012 (13)	0.0266 (4)
H7	0.1936	−0.1312	0.9357	0.032*
C8	−0.0236 (2)	−0.08537 (7)	0.86104 (13)	0.0249 (4)
C9	−0.08557 (19)	−0.02749 (7)	0.82836 (12)	0.0238 (4)
C10	−0.2640 (2)	−0.02089 (7)	0.78388 (13)	0.0272 (4)
H10	−0.3097	0.0174	0.7653	0.033*
C11	−0.3711 (2)	−0.06874 (8)	0.76733 (14)	0.0328 (4)
H11	−0.4899	−0.0632	0.7372	0.039*
C12	−0.3080 (2)	−0.12620 (8)	0.79428 (15)	0.0342 (4)
H12	−0.3825	−0.1593	0.7792	0.041*
C13	−0.1390 (2)	−0.13381 (7)	0.84225 (14)	0.0311 (4)
H13	−0.0978	−0.1724	0.8635	0.037*
C14	0.0722 (2)	0.18961 (7)	0.84212 (15)	0.0305 (4)
C15	0.2164 (2)	0.23259 (7)	0.88335 (17)	0.0352 (4)
H15A	0.2239	0.2383	0.9708	0.042*
H15B	0.1868	0.2711	0.8444	0.042*
C16	0.3943 (2)	0.21341 (7)	0.85643 (16)	0.0322 (4)
C17	0.4295 (2)	0.15108 (7)	0.90742 (14)	0.0275 (4)
H17A	0.5303	0.1344	0.8761	0.033*
H17B	0.4594	0.1537	0.9956	0.033*
C18	0.3939 (2)	0.21340 (8)	0.72089 (17)	0.0412 (5)
H18A	0.3564	0.2521	0.6880	0.062*
H18B	0.3146	0.1830	0.6836	0.062*
H18C	0.5106	0.2051	0.7044	0.062*
C19	0.5342 (2)	0.25523 (8)	0.9164 (2)	0.0473 (5)
H19A	0.6479	0.2401	0.9058	0.071*
H19B	0.5274	0.2581	1.0020	0.071*
H19C	0.5173	0.2944	0.8798	0.071*
C20	−0.07830 (19)	0.08847 (6)	0.66195 (13)	0.0217 (3)
C21	0.03606 (19)	0.07426 (6)	0.58126 (13)	0.0218 (3)
C22	−0.0157 (2)	0.08026 (7)	0.45887 (13)	0.0250 (4)
H22	0.0609	0.0697	0.4050	0.030*
C23	−0.1784 (2)	0.10161 (7)	0.41493 (14)	0.0279 (4)
H23	−0.2132	0.1054	0.3310	0.033*
C24	−0.2910 (2)	0.11751 (7)	0.49250 (14)	0.0277 (4)
H24	−0.4017	0.1330	0.4625	0.033*
C25	−0.2392 (2)	0.11041 (6)	0.61498 (14)	0.0245 (4)
H25	−0.3169	0.1210	0.6681	0.029*
C26	0.3182 (2)	0.04429 (7)	0.55369 (15)	0.0296 (4)
H26A	0.2763	0.0126	0.4978	0.044*
H26B	0.4286	0.0327	0.6007	0.044*
H26C	0.3341	0.0803	0.5087	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0227 (6)	0.0247 (6)	0.0265 (6)	−0.0001 (4)	−0.0007 (5)	0.0011 (4)
O2	0.0281 (7)	0.0341 (7)	0.0693 (9)	0.0077 (5)	0.0024 (6)	−0.0136 (6)
O3	0.0208 (6)	0.0320 (6)	0.0223 (6)	0.0042 (5)	0.0041 (5)	−0.0003 (4)
C1	0.0275 (9)	0.0259 (8)	0.0182 (7)	0.0012 (7)	0.0032 (6)	−0.0024 (6)
C2	0.0232 (8)	0.0276 (8)	0.0203 (8)	0.0011 (6)	0.0037 (6)	−0.0042 (6)
C3	0.0216 (8)	0.0261 (8)	0.0205 (8)	0.0023 (6)	0.0046 (6)	−0.0024 (6)
C4	0.0246 (9)	0.0281 (8)	0.0137 (7)	0.0012 (6)	0.0039 (6)	−0.0012 (6)
C5	0.0234 (8)	0.0280 (8)	0.0173 (7)	−0.0028 (6)	0.0032 (6)	−0.0013 (6)
C6	0.0251 (9)	0.0316 (9)	0.0201 (8)	0.0023 (7)	0.0007 (7)	−0.0005 (6)
C7	0.0336 (9)	0.0256 (8)	0.0210 (8)	0.0021 (7)	0.0055 (7)	0.0011 (6)
C8	0.0292 (9)	0.0292 (8)	0.0171 (7)	−0.0016 (7)	0.0061 (7)	−0.0012 (6)
C9	0.0253 (9)	0.0314 (8)	0.0151 (7)	−0.0016 (7)	0.0047 (6)	−0.0018 (6)
C10	0.0266 (9)	0.0344 (9)	0.0209 (8)	−0.0023 (7)	0.0050 (7)	−0.0002 (6)
C11	0.0286 (9)	0.0461 (10)	0.0239 (8)	−0.0055 (8)	0.0049 (7)	0.0000 (7)
C12	0.0367 (10)	0.0386 (10)	0.0282 (9)	−0.0131 (8)	0.0073 (8)	−0.0026 (7)
C13	0.0382 (10)	0.0309 (9)	0.0256 (8)	−0.0041 (7)	0.0090 (7)	0.0009 (7)
C14	0.0265 (9)	0.0308 (9)	0.0346 (9)	0.0035 (7)	0.0060 (7)	−0.0067 (7)
C15	0.0310 (10)	0.0276 (9)	0.0471 (11)	0.0017 (7)	0.0061 (8)	−0.0097 (7)
C16	0.0278 (9)	0.0250 (8)	0.0438 (10)	0.0013 (7)	0.0054 (8)	−0.0029 (7)
C17	0.0245 (9)	0.0288 (9)	0.0289 (8)	−0.0014 (7)	0.0026 (7)	−0.0037 (7)
C18	0.0436 (11)	0.0340 (10)	0.0483 (11)	0.0069 (8)	0.0148 (9)	0.0105 (8)
C19	0.0320 (11)	0.0333 (10)	0.0761 (15)	−0.0040 (8)	0.0066 (10)	−0.0085 (9)
C20	0.0224 (8)	0.0193 (7)	0.0231 (8)	−0.0006 (6)	0.0024 (6)	−0.0003 (6)
C21	0.0210 (8)	0.0207 (7)	0.0228 (8)	−0.0007 (6)	0.0008 (6)	0.0004 (6)
C22	0.0275 (9)	0.0256 (8)	0.0220 (8)	−0.0028 (6)	0.0045 (7)	0.0006 (6)
C23	0.0303 (9)	0.0304 (9)	0.0212 (8)	−0.0051 (7)	−0.0016 (7)	0.0055 (6)
C24	0.0225 (9)	0.0279 (8)	0.0306 (9)	−0.0012 (7)	−0.0027 (7)	0.0071 (7)
C25	0.0224 (8)	0.0235 (8)	0.0281 (8)	0.0002 (6)	0.0053 (7)	0.0009 (6)
C26	0.0253 (9)	0.0351 (9)	0.0303 (9)	0.0033 (7)	0.0106 (7)	0.0013 (7)

Geometric parameters (Å, º) top

O1—C1	1.3689 (18)	C14—C15	1.511 (2)
O1—C5	1.3907 (18)	C15—C16	1.537 (2)
O2—C14	1.227 (2)	C15—H15A	0.9900
O3—C21	1.3647 (18)	C15—H15B	0.9900
O3—C26	1.4274 (17)	C16—C19	1.528 (2)
C1—C2	1.340 (2)	C16—C18	1.532 (2)
C1—C17	1.488 (2)	C16—C17	1.535 (2)
C2—C14	1.466 (2)	C17—H17A	0.9900
C2—C3	1.514 (2)	C17—H17B	0.9900
C3—C4	1.519 (2)	C18—H18A	0.9800
C3—C20	1.529 (2)	C18—H18B	0.9800
C3—H3	1.0000	C18—H18C	0.9800
C4—C5	1.370 (2)	C19—H19A	0.9800
C4—C9	1.433 (2)	C19—H19B	0.9800
C5—C6	1.409 (2)	C19—H19C	0.9800
C6—C7	1.365 (2)	C20—C25	1.384 (2)
C6—H6	0.9500	C20—C21	1.412 (2)
C7—C8	1.418 (2)	C21—C22	1.388 (2)
C7—H7	0.9500	C22—C23	1.384 (2)
C8—C13	1.418 (2)	C22—H22	0.9500
C8—C9	1.428 (2)	C23—C24	1.385 (2)
C9—C10	1.420 (2)	C23—H23	0.9500
C10—C11	1.367 (2)	C24—C25	1.391 (2)
C10—H10	0.9500	C24—H24	0.9500
C11—C12	1.410 (2)	C25—H25	0.9500
C11—H11	0.9500	C26—H26A	0.9800
C12—C13	1.364 (2)	C26—H26B	0.9800
C12—H12	0.9500	C26—H26C	0.9800
C13—H13	0.9500

C1—O1—C5	118.04 (12)	C16—C15—H15B	108.6
C21—O3—C26	117.06 (11)	H15A—C15—H15B	107.6
C2—C1—O1	122.93 (14)	C19—C16—C18	109.51 (15)
C2—C1—C17	125.79 (14)	C19—C16—C17	109.22 (14)
O1—C1—C17	111.27 (13)	C18—C16—C17	110.37 (13)
C1—C2—C14	118.75 (14)	C19—C16—C15	110.43 (14)
C1—C2—C3	122.43 (14)	C18—C16—C15	109.70 (15)
C14—C2—C3	118.82 (13)	C17—C16—C15	107.60 (13)
C2—C3—C4	109.91 (13)	C1—C17—C16	113.13 (13)
C2—C3—C20	110.14 (12)	C1—C17—H17A	109.0
C4—C3—C20	113.79 (12)	C16—C17—H17A	109.0
C2—C3—H3	107.6	C1—C17—H17B	109.0
C4—C3—H3	107.6	C16—C17—H17B	109.0
C20—C3—H3	107.6	H17A—C17—H17B	107.8
C5—C4—C9	117.64 (14)	C16—C18—H18A	109.5
C5—C4—C3	120.53 (14)	C16—C18—H18B	109.5
C9—C4—C3	121.81 (14)	H18A—C18—H18B	109.5
C4—C5—O1	123.12 (14)	C16—C18—H18C	109.5
C4—C5—C6	123.30 (14)	H18A—C18—H18C	109.5
O1—C5—C6	113.58 (13)	H18B—C18—H18C	109.5
C7—C6—C5	119.42 (15)	C16—C19—H19A	109.5
C7—C6—H6	120.3	C16—C19—H19B	109.5
C5—C6—H6	120.3	H19A—C19—H19B	109.5
C6—C7—C8	120.55 (15)	C16—C19—H19C	109.5
C6—C7—H7	119.7	H19A—C19—H19C	109.5
C8—C7—H7	119.7	H19B—C19—H19C	109.5
C7—C8—C13	121.56 (15)	C25—C20—C21	117.83 (14)
C7—C8—C9	119.20 (14)	C25—C20—C3	120.50 (13)
C13—C8—C9	119.24 (15)	C21—C20—C3	121.61 (13)
C10—C9—C8	117.79 (14)	O3—C21—C22	124.02 (13)
C10—C9—C4	122.44 (15)	O3—C21—C20	115.66 (13)
C8—C9—C4	119.75 (14)	C22—C21—C20	120.32 (14)
C11—C10—C9	121.07 (16)	C23—C22—C21	120.27 (14)
C11—C10—H10	119.5	C23—C22—H22	119.9
C9—C10—H10	119.5	C21—C22—H22	119.9
C10—C11—C12	121.03 (16)	C22—C23—C24	120.44 (14)
C10—C11—H11	119.5	C22—C23—H23	119.8
C12—C11—H11	119.5	C24—C23—H23	119.8
C13—C12—C11	119.36 (16)	C23—C24—C25	118.95 (15)
C13—C12—H12	120.3	C23—C24—H24	120.5
C11—C12—H12	120.3	C25—C24—H24	120.5
C12—C13—C8	121.38 (16)	C20—C25—C24	122.15 (14)
C12—C13—H13	119.3	C20—C25—H25	118.9
C8—C13—H13	119.3	C24—C25—H25	118.9
O2—C14—C2	121.23 (15)	O3—C26—H26A	109.5
O2—C14—C15	121.08 (15)	O3—C26—H26B	109.5
C2—C14—C15	117.61 (14)	H26A—C26—H26B	109.5
C14—C15—C16	114.58 (13)	O3—C26—H26C	109.5
C14—C15—H15A	108.6	H26A—C26—H26C	109.5
C16—C15—H15A	108.6	H26B—C26—H26C	109.5
C14—C15—H15B	108.6

C5—O1—C1—C2	−7.5 (2)	C10—C11—C12—C13	2.7 (2)
C5—O1—C1—C17	171.74 (11)	C11—C12—C13—C8	−2.6 (2)
O1—C1—C2—C14	172.34 (13)	C7—C8—C13—C12	−179.56 (14)
C17—C1—C2—C14	−6.8 (2)	C9—C8—C13—C12	−0.4 (2)
O1—C1—C2—C3	−8.5 (2)	C1—C2—C14—O2	−176.29 (15)
C17—C1—C2—C3	172.37 (13)	C3—C2—C14—O2	4.5 (2)
C1—C2—C3—C4	18.08 (19)	C1—C2—C14—C15	0.6 (2)
C14—C2—C3—C4	−162.79 (13)	C3—C2—C14—C15	−178.59 (14)
C1—C2—C3—C20	−108.08 (16)	O2—C14—C15—C16	−152.27 (17)
C14—C2—C3—C20	71.06 (16)	C2—C14—C15—C16	30.9 (2)
C2—C3—C4—C5	−13.38 (18)	C14—C15—C16—C19	−172.21 (15)
C20—C3—C4—C5	110.68 (15)	C14—C15—C16—C18	67.01 (19)
C2—C3—C4—C9	168.47 (12)	C14—C15—C16—C17	−53.1 (2)
C20—C3—C4—C9	−67.47 (17)	C2—C1—C17—C16	−18.7 (2)
C9—C4—C5—O1	177.63 (12)	O1—C1—C17—C16	162.09 (12)
C3—C4—C5—O1	−0.6 (2)	C19—C16—C17—C1	166.24 (13)
C9—C4—C5—C6	−1.5 (2)	C18—C16—C17—C1	−73.32 (17)
C3—C4—C5—C6	−179.70 (13)	C15—C16—C17—C1	46.35 (18)
C1—O1—C5—C4	12.10 (19)	C2—C3—C20—C25	−111.05 (15)
C1—O1—C5—C6	−168.71 (12)	C4—C3—C20—C25	125.02 (15)
C4—C5—C6—C7	2.7 (2)	C2—C3—C20—C21	66.04 (17)
O1—C5—C6—C7	−176.49 (12)	C4—C3—C20—C21	−57.89 (18)
C5—C6—C7—C8	−0.3 (2)	C26—O3—C21—C22	4.4 (2)
C6—C7—C8—C13	176.18 (14)	C26—O3—C21—C20	−175.59 (12)
C6—C7—C8—C9	−3.0 (2)	C25—C20—C21—O3	177.57 (12)
C7—C8—C9—C10	−177.55 (13)	C3—C20—C21—O3	0.4 (2)
C13—C8—C9—C10	3.2 (2)	C25—C20—C21—C22	−2.4 (2)
C7—C8—C9—C4	4.2 (2)	C3—C20—C21—C22	−179.53 (13)
C13—C8—C9—C4	−175.03 (13)	O3—C21—C22—C23	−178.35 (14)
C5—C4—C9—C10	179.85 (12)	C20—C21—C22—C23	1.6 (2)
C3—C4—C9—C10	−2.0 (2)	C21—C22—C23—C24	0.4 (2)
C5—C4—C9—C8	−2.0 (2)	C22—C23—C24—C25	−1.4 (2)
C3—C4—C9—C8	176.22 (12)	C21—C20—C25—C24	1.3 (2)
C8—C9—C10—C11	−3.2 (2)	C3—C20—C25—C24	178.48 (14)
C4—C9—C10—C11	175.03 (14)	C23—C24—C25—C20	0.6 (2)
C9—C10—C11—C12	0.2 (2)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄O₃
M_r	384.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	7.8454 (11), 22.670 (3), 11.3100 (13)
β (°)	98.893 (4)
V (Å³)	1987.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.36 × 0.28 × 0.20

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.970, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	12038, 3860, 3274
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.122, 1.09
No. of reflections	3860
No. of parameters	266
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.21

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors thank the Tangshan Municipal Science and Technology Commission (grant No. 07160213B) and Tangshan Normal College (grant No. 07A02) for financial support.

References

Lambert, R. W., Martin, J. A., Merrett, J. H., Parkes, K. E. B. & Thomas, G. J. (1997). PCT Int. Appl. WO 9706178. Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar