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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o119.
Published online 2009 December 12. doi:  10.1107/S1600536809052210
PMCID: PMC2980265

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

Abstract

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 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o119-scheme1.jpg

Experimental

Crystal data

  • C26H24O3
  • M r = 384.45
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o119-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.122
  • S = 1.09
  • 3860 reflections
  • 266 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.21 e Å−3

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

Supplementary Material

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

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

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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.

Refinement

All H atoms were included in the refinement in the riding model approximation, with C—H = 0.95–1.00 Å, and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms.

Figures

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

Crystal data

C26H24O3F(000) = 816
Mr = 384.45Dx = 1.285 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71070 Å
a = 7.8454 (11) ÅCell parameters from 3867 reflections
b = 22.670 (3) Åθ = 1.8–27.2°
c = 11.3100 (13) ŵ = 0.08 mm1
β = 98.893 (4)°T = 113 K
V = 1987.4 (5) Å3Block, colorless
Z = 40.36 × 0.28 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer3860 independent reflections
Radiation source: rotating anode3274 reflections with I > 2σ(I)
confocalRint = 0.035
Detector resolution: 7.31 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω and [var phi] scansh = −9→8
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)k = −27→20
Tmin = 0.970, Tmax = 0.985l = −13→13
12038 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.122w = 1/[σ2(Fo2) + (0.0629P)2 + 0.2114P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
3860 reflectionsΔρmax = 0.29 e Å3
266 parametersΔρmin = −0.21 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (2)

Special details

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)

xyzUiso*/Ueq
O10.32998 (13)0.05276 (4)0.89201 (9)0.0251 (3)
O2−0.07739 (15)0.20650 (5)0.81569 (13)0.0444 (4)
O30.19539 (13)0.05495 (5)0.63209 (9)0.0249 (3)
C10.2801 (2)0.11049 (7)0.87702 (13)0.0239 (4)
C20.11615 (19)0.12678 (7)0.84090 (13)0.0237 (4)
C3−0.0248 (2)0.08279 (6)0.79729 (13)0.0226 (3)
H3−0.12740.09300.83580.027*
C40.03259 (19)0.02110 (7)0.83795 (12)0.0220 (3)
C50.20193 (19)0.00984 (7)0.88233 (12)0.0229 (3)
C60.2635 (2)−0.04641 (7)0.92099 (13)0.0259 (4)
H60.3813−0.05180.95430.031*
C70.1525 (2)−0.09314 (7)0.91012 (13)0.0266 (4)
H70.1936−0.13120.93570.032*
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)
H10−0.30970.01740.76530.033*
C11−0.3711 (2)−0.06874 (8)0.76733 (14)0.0328 (4)
H11−0.4899−0.06320.73720.039*
C12−0.3080 (2)−0.12620 (8)0.79428 (15)0.0342 (4)
H12−0.3825−0.15930.77920.041*
C13−0.1390 (2)−0.13381 (7)0.84225 (14)0.0311 (4)
H13−0.0978−0.17240.86350.037*
C140.0722 (2)0.18961 (7)0.84212 (15)0.0305 (4)
C150.2164 (2)0.23259 (7)0.88335 (17)0.0352 (4)
H15A0.22390.23830.97080.042*
H15B0.18680.27110.84440.042*
C160.3943 (2)0.21341 (7)0.85643 (16)0.0322 (4)
C170.4295 (2)0.15108 (7)0.90742 (14)0.0275 (4)
H17A0.53030.13440.87610.033*
H17B0.45940.15370.99560.033*
C180.3939 (2)0.21340 (8)0.72089 (17)0.0412 (5)
H18A0.35640.25210.68800.062*
H18B0.31460.18300.68360.062*
H18C0.51060.20510.70440.062*
C190.5342 (2)0.25523 (8)0.9164 (2)0.0473 (5)
H19A0.64790.24010.90580.071*
H19B0.52740.25811.00200.071*
H19C0.51730.29440.87980.071*
C20−0.07830 (19)0.08847 (6)0.66195 (13)0.0217 (3)
C210.03606 (19)0.07426 (6)0.58126 (13)0.0218 (3)
C22−0.0157 (2)0.08026 (7)0.45887 (13)0.0250 (4)
H220.06090.06970.40500.030*
C23−0.1784 (2)0.10161 (7)0.41493 (14)0.0279 (4)
H23−0.21320.10540.33100.033*
C24−0.2910 (2)0.11751 (7)0.49250 (14)0.0277 (4)
H24−0.40170.13300.46250.033*
C25−0.2392 (2)0.11041 (6)0.61498 (14)0.0245 (4)
H25−0.31690.12100.66810.029*
C260.3182 (2)0.04429 (7)0.55369 (15)0.0296 (4)
H26A0.27630.01260.49780.044*
H26B0.42860.03270.60070.044*
H26C0.33410.08030.50870.044*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0227 (6)0.0247 (6)0.0265 (6)−0.0001 (4)−0.0007 (5)0.0011 (4)
O20.0281 (7)0.0341 (7)0.0693 (9)0.0077 (5)0.0024 (6)−0.0136 (6)
O30.0208 (6)0.0320 (6)0.0223 (6)0.0042 (5)0.0041 (5)−0.0003 (4)
C10.0275 (9)0.0259 (8)0.0182 (7)0.0012 (7)0.0032 (6)−0.0024 (6)
C20.0232 (8)0.0276 (8)0.0203 (8)0.0011 (6)0.0037 (6)−0.0042 (6)
C30.0216 (8)0.0261 (8)0.0205 (8)0.0023 (6)0.0046 (6)−0.0024 (6)
C40.0246 (9)0.0281 (8)0.0137 (7)0.0012 (6)0.0039 (6)−0.0012 (6)
C50.0234 (8)0.0280 (8)0.0173 (7)−0.0028 (6)0.0032 (6)−0.0013 (6)
C60.0251 (9)0.0316 (9)0.0201 (8)0.0023 (7)0.0007 (7)−0.0005 (6)
C70.0336 (9)0.0256 (8)0.0210 (8)0.0021 (7)0.0055 (7)0.0011 (6)
C80.0292 (9)0.0292 (8)0.0171 (7)−0.0016 (7)0.0061 (7)−0.0012 (6)
C90.0253 (9)0.0314 (8)0.0151 (7)−0.0016 (7)0.0047 (6)−0.0018 (6)
C100.0266 (9)0.0344 (9)0.0209 (8)−0.0023 (7)0.0050 (7)−0.0002 (6)
C110.0286 (9)0.0461 (10)0.0239 (8)−0.0055 (8)0.0049 (7)0.0000 (7)
C120.0367 (10)0.0386 (10)0.0282 (9)−0.0131 (8)0.0073 (8)−0.0026 (7)
C130.0382 (10)0.0309 (9)0.0256 (8)−0.0041 (7)0.0090 (7)0.0009 (7)
C140.0265 (9)0.0308 (9)0.0346 (9)0.0035 (7)0.0060 (7)−0.0067 (7)
C150.0310 (10)0.0276 (9)0.0471 (11)0.0017 (7)0.0061 (8)−0.0097 (7)
C160.0278 (9)0.0250 (8)0.0438 (10)0.0013 (7)0.0054 (8)−0.0029 (7)
C170.0245 (9)0.0288 (9)0.0289 (8)−0.0014 (7)0.0026 (7)−0.0037 (7)
C180.0436 (11)0.0340 (10)0.0483 (11)0.0069 (8)0.0148 (9)0.0105 (8)
C190.0320 (11)0.0333 (10)0.0761 (15)−0.0040 (8)0.0066 (10)−0.0085 (9)
C200.0224 (8)0.0193 (7)0.0231 (8)−0.0006 (6)0.0024 (6)−0.0003 (6)
C210.0210 (8)0.0207 (7)0.0228 (8)−0.0007 (6)0.0008 (6)0.0004 (6)
C220.0275 (9)0.0256 (8)0.0220 (8)−0.0028 (6)0.0045 (7)0.0006 (6)
C230.0303 (9)0.0304 (9)0.0212 (8)−0.0051 (7)−0.0016 (7)0.0055 (6)
C240.0225 (9)0.0279 (8)0.0306 (9)−0.0012 (7)−0.0027 (7)0.0071 (7)
C250.0224 (8)0.0235 (8)0.0281 (8)0.0002 (6)0.0053 (7)0.0009 (6)
C260.0253 (9)0.0351 (9)0.0303 (9)0.0033 (7)0.0106 (7)0.0013 (7)

Geometric parameters (Å, °)

O1—C11.3689 (18)C14—C151.511 (2)
O1—C51.3907 (18)C15—C161.537 (2)
O2—C141.227 (2)C15—H15A0.9900
O3—C211.3647 (18)C15—H15B0.9900
O3—C261.4274 (17)C16—C191.528 (2)
C1—C21.340 (2)C16—C181.532 (2)
C1—C171.488 (2)C16—C171.535 (2)
C2—C141.466 (2)C17—H17A0.9900
C2—C31.514 (2)C17—H17B0.9900
C3—C41.519 (2)C18—H18A0.9800
C3—C201.529 (2)C18—H18B0.9800
C3—H31.0000C18—H18C0.9800
C4—C51.370 (2)C19—H19A0.9800
C4—C91.433 (2)C19—H19B0.9800
C5—C61.409 (2)C19—H19C0.9800
C6—C71.365 (2)C20—C251.384 (2)
C6—H60.9500C20—C211.412 (2)
C7—C81.418 (2)C21—C221.388 (2)
C7—H70.9500C22—C231.384 (2)
C8—C131.418 (2)C22—H220.9500
C8—C91.428 (2)C23—C241.385 (2)
C9—C101.420 (2)C23—H230.9500
C10—C111.367 (2)C24—C251.391 (2)
C10—H100.9500C24—H240.9500
C11—C121.410 (2)C25—H250.9500
C11—H110.9500C26—H26A0.9800
C12—C131.364 (2)C26—H26B0.9800
C12—H120.9500C26—H26C0.9800
C13—H130.9500
C1—O1—C5118.04 (12)C16—C15—H15B108.6
C21—O3—C26117.06 (11)H15A—C15—H15B107.6
C2—C1—O1122.93 (14)C19—C16—C18109.51 (15)
C2—C1—C17125.79 (14)C19—C16—C17109.22 (14)
O1—C1—C17111.27 (13)C18—C16—C17110.37 (13)
C1—C2—C14118.75 (14)C19—C16—C15110.43 (14)
C1—C2—C3122.43 (14)C18—C16—C15109.70 (15)
C14—C2—C3118.82 (13)C17—C16—C15107.60 (13)
C2—C3—C4109.91 (13)C1—C17—C16113.13 (13)
C2—C3—C20110.14 (12)C1—C17—H17A109.0
C4—C3—C20113.79 (12)C16—C17—H17A109.0
C2—C3—H3107.6C1—C17—H17B109.0
C4—C3—H3107.6C16—C17—H17B109.0
C20—C3—H3107.6H17A—C17—H17B107.8
C5—C4—C9117.64 (14)C16—C18—H18A109.5
C5—C4—C3120.53 (14)C16—C18—H18B109.5
C9—C4—C3121.81 (14)H18A—C18—H18B109.5
C4—C5—O1123.12 (14)C16—C18—H18C109.5
C4—C5—C6123.30 (14)H18A—C18—H18C109.5
O1—C5—C6113.58 (13)H18B—C18—H18C109.5
C7—C6—C5119.42 (15)C16—C19—H19A109.5
C7—C6—H6120.3C16—C19—H19B109.5
C5—C6—H6120.3H19A—C19—H19B109.5
C6—C7—C8120.55 (15)C16—C19—H19C109.5
C6—C7—H7119.7H19A—C19—H19C109.5
C8—C7—H7119.7H19B—C19—H19C109.5
C7—C8—C13121.56 (15)C25—C20—C21117.83 (14)
C7—C8—C9119.20 (14)C25—C20—C3120.50 (13)
C13—C8—C9119.24 (15)C21—C20—C3121.61 (13)
C10—C9—C8117.79 (14)O3—C21—C22124.02 (13)
C10—C9—C4122.44 (15)O3—C21—C20115.66 (13)
C8—C9—C4119.75 (14)C22—C21—C20120.32 (14)
C11—C10—C9121.07 (16)C23—C22—C21120.27 (14)
C11—C10—H10119.5C23—C22—H22119.9
C9—C10—H10119.5C21—C22—H22119.9
C10—C11—C12121.03 (16)C22—C23—C24120.44 (14)
C10—C11—H11119.5C22—C23—H23119.8
C12—C11—H11119.5C24—C23—H23119.8
C13—C12—C11119.36 (16)C23—C24—C25118.95 (15)
C13—C12—H12120.3C23—C24—H24120.5
C11—C12—H12120.3C25—C24—H24120.5
C12—C13—C8121.38 (16)C20—C25—C24122.15 (14)
C12—C13—H13119.3C20—C25—H25118.9
C8—C13—H13119.3C24—C25—H25118.9
O2—C14—C2121.23 (15)O3—C26—H26A109.5
O2—C14—C15121.08 (15)O3—C26—H26B109.5
C2—C14—C15117.61 (14)H26A—C26—H26B109.5
C14—C15—C16114.58 (13)O3—C26—H26C109.5
C14—C15—H15A108.6H26A—C26—H26C109.5
C16—C15—H15A108.6H26B—C26—H26C109.5
C14—C15—H15B108.6
C5—O1—C1—C2−7.5 (2)C10—C11—C12—C132.7 (2)
C5—O1—C1—C17171.74 (11)C11—C12—C13—C8−2.6 (2)
O1—C1—C2—C14172.34 (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—C3172.37 (13)C3—C2—C14—O24.5 (2)
C1—C2—C3—C418.08 (19)C1—C2—C14—C150.6 (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—C2071.06 (16)C2—C14—C15—C1630.9 (2)
C2—C3—C4—C5−13.38 (18)C14—C15—C16—C19−172.21 (15)
C20—C3—C4—C5110.68 (15)C14—C15—C16—C1867.01 (19)
C2—C3—C4—C9168.47 (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—O1177.63 (12)O1—C1—C17—C16162.09 (12)
C3—C4—C5—O1−0.6 (2)C19—C16—C17—C1166.24 (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—C146.35 (18)
C1—O1—C5—C412.10 (19)C2—C3—C20—C25−111.05 (15)
C1—O1—C5—C6−168.71 (12)C4—C3—C20—C25125.02 (15)
C4—C5—C6—C72.7 (2)C2—C3—C20—C2166.04 (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—C224.4 (2)
C6—C7—C8—C13176.18 (14)C26—O3—C21—C20−175.59 (12)
C6—C7—C8—C9−3.0 (2)C25—C20—C21—O3177.57 (12)
C7—C8—C9—C10−177.55 (13)C3—C20—C21—O30.4 (2)
C13—C8—C9—C103.2 (2)C25—C20—C21—C22−2.4 (2)
C7—C8—C9—C44.2 (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—C10179.85 (12)C20—C21—C22—C231.6 (2)
C3—C4—C9—C10−2.0 (2)C21—C22—C23—C240.4 (2)
C5—C4—C9—C8−2.0 (2)C22—C23—C24—C25−1.4 (2)
C3—C4—C9—C8176.22 (12)C21—C20—C25—C241.3 (2)
C8—C9—C10—C11−3.2 (2)C3—C20—C25—C24178.48 (14)
C4—C9—C10—C11175.03 (14)C23—C24—C25—C200.6 (2)
C9—C10—C11—C120.2 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2168).

References

  • Lambert, R. W., Martin, J. A., Merrett, J. H., Parkes, K. E. B. & Thomas, G. J. (1997). PCT Int. Appl. WO 9706178.
  • Rigaku/MSC (2005). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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