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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o519.
Published online 2008 January 25. doi:  10.1107/S1600536808002183
PMCID: PMC2960184

9-(2,3-Dichloro­phen­yl)-4a-hydr­oxy-3,3,6,6-tetra­methyl-4,4a,5,6,9,9a-hexa­hydro-3H-xanthene-1,8(2H,7H)-dione

Abstract

Mol­ecules of the title compound, C23H26Cl2O4, are linked by hydrogen bonds between the hydroxyl O atom and the carbonyl O atom of a neighboring mol­ecule. The central hydropyran and fused cyclohexanone rings adopt half-chair conformations, while the fused hydroxycyclohexanone ring adopts a chair conformation.

Related literature

For the synthesis of xanthenes, see: Kantevari et al. (2006 [triangle]); Lin et al. (2007 [triangle]). For therapeutic effects, see: Sirkecioglu et al. (1995 [triangle]).

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Object name is e-64-0o519-scheme1.jpg

Experimental

Crystal data

  • C23H26Cl2O4
  • M r = 437.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o519-efi1.jpg
  • a = 11.9581 (17) Å
  • b = 15.165 (2) Å
  • c = 12.3953 (18) Å
  • β = 105.357 (13)°
  • V = 2167.5 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.33 mm−1
  • T = 290 (2) K
  • 0.22 × 0.10 × 0.09 mm

Data collection

  • Stoe IPDS diffractometer
  • Absorption correction: numerical (X-RED; Stoe & Cie, 1997 [triangle]) T min = 0.930, T max = 0.969
  • 13922 measured reflections
  • 4012 independent reflections
  • 1511 reflections with I > 2σ(I)
  • R int = 0.070

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.162
  • S = 0.85
  • 4012 reflections
  • 246 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.73 e Å−3
  • Δρmin = −0.83 e Å−3

Data collection: IPDS Software (Stoe & Cie, 1997 [triangle]); cell refinement: IPDS Software; data reduction: IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 2001 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002183/ng2413sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002183/ng2413Isup2.hkl

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

Acknowledgments

This work was supported by grants from the University of Tehran and the University of Alzahra.

supplementary crystallographic information

Comment

Xanthenes and benzoxanthenes have received much attention because of their wide range of therapeutic and biological properties (Sirkecioglu, et al., 1995). During our study for the synthesis of octahydroquinazolinone (Lin, et al., 2007; Kantevari et al., 2006), we observed that in the reaction conditions, the formation of 1,8-dioxo-octahydroxanthene was occurred in excellent yields in the presence of activated SBA-sulfonic acid as new nanoporous catalyst.

The molecular and atom-labeling scheme for (I) are shwon in Fig.1. The relatively strong, O2—H22···O3, 2.879 (4) Å hydrogen bonds between the neigbouring molecules, seems to be stabilized the crystal structure (Fig. 2). Ring A cyclohex-2-enone (C6/C14/C13/C21/C20/C16) and ring B cyclohexanone (C1/C4/C10/C12/C7/C5) are of course not planar. The C6?C14 can be in resonance with C13?O3, which make the ring A more planar than the ring B. This effect can also be checked by comparing nearly planar torsion angle of O3—C13—C14—C6, 174.1 (4)°, while the torsion angle of O4—C4—C1—C5 found to be -123.8 (4)°.

Experimental

A mixture of 5,5-dimethyl-1,3-cyclohexanedione (dimedone) (10 mmol, 1.04 g), 2,3-dichlorobenzaldehyde (10 mmol), urea (15 mmol) and activated SBA-sulfonic acid (0.02 g) was heated at 80°C. The reaction was monitored by TLC. After 5 minutes, the reaction was completely solidified. The solid was washed with water and filtered. The crude product was dissolved in hot EtOH and filtered to remove the catalyst. The crystals was appeared after slow cooling. Recystallization did not yield larger crystals.

Refinement

H atoms were geometrically positioned except hydroxyl group which is located on electron desity map and all constrained to ride on their parent atoms, with Uiso(H) = 1.5Ueq(for methyl group and for the rest 1.2).

Figures

Fig. 1.
Molecular structure of (I), with 50% probability displacement ellipsoids. H atoms are shown as circles of arbitrary radii.
Fig. 2.
Packing view for (I), showing hydrgen bonding

Crystal data

C23H26Cl2O4F000 = 920
Mr = 437.34Dx = 1.340 Mg m3
Monoclinic, P21/aMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yabCell parameters from 13922 reflections
a = 11.9581 (17) Åθ = 3.3–25.5º
b = 15.165 (2) ŵ = 0.33 mm1
c = 12.3953 (18) ÅT = 290 (2) K
β = 105.357 (13)ºBlock shape, colorless
V = 2167.5 (5) Å30.22 × 0.10 × 0.09 mm
Z = 4

Data collection

Stoe IPDS diffractometer4012 independent reflections
Radiation source: fine-focus sealed tube1511 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.070
T = 290(2) Kθmax = 25.5º
[var phi] oscillation scansθmin = 3.7º
Absorption correction: numerical(X-RED; Stoe & Cie, 1997)h = −14→12
Tmin = 0.930, Tmax = 0.969k = −17→18
13922 measured reflectionsl = −15→15

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.060  w = 1/[σ2(Fo2) + (0.08P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.162(Δ/σ)max < 0.001
S = 0.85Δρmax = 0.73 e Å3
4012 reflectionsΔρmin = −0.83 e Å3
246 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0056 (13)
Secondary atom site location: difference Fourier map

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
Cl10.74989 (9)0.77065 (8)−0.11681 (10)0.0535 (4)
Cl20.80090 (12)0.65780 (9)−0.30989 (10)0.0694 (5)
O11.1085 (2)0.84256 (18)0.2731 (2)0.0445 (8)
O21.1313 (2)0.8477 (2)0.0944 (3)0.0469 (9)
H221.197 (4)0.851 (3)0.130 (4)0.056*
O30.8621 (3)0.59442 (19)0.2062 (3)0.0532 (9)
O40.7952 (3)0.8634 (2)0.2112 (3)0.0571 (9)
C10.9390 (3)0.8517 (3)0.1106 (3)0.0315 (10)
H10.91880.86990.03190.038*
C20.9459 (3)0.7008 (3)0.0160 (4)0.0337 (11)
C30.9198 (3)0.7533 (3)0.1118 (3)0.0365 (11)
H30.83710.74490.10560.044*
C40.8591 (4)0.9029 (3)0.1672 (4)0.0398 (11)
C51.0648 (3)0.8800 (3)0.1620 (4)0.0347 (11)
C61.0712 (4)0.7622 (3)0.2944 (4)0.0415 (11)
C71.0802 (3)0.9788 (3)0.1793 (3)0.0367 (11)
H7A1.07511.00570.10710.044*
H7B1.15800.98940.22590.044*
C80.8930 (4)0.6534 (3)−0.1764 (4)0.0487 (13)
C90.8717 (4)0.7044 (3)−0.0908 (4)0.0370 (11)
C100.8714 (4)0.9994 (3)0.1684 (4)0.0447 (12)
H10A0.81571.02560.20340.054*
H10B0.85491.02110.09220.054*
C111.0414 (4)0.6451 (3)0.0339 (4)0.0473 (12)
H111.09320.64230.10450.057*
C120.9942 (4)1.0271 (3)0.2326 (4)0.0397 (11)
C130.9474 (4)0.6348 (3)0.2614 (4)0.0507 (13)
C140.9840 (4)0.7182 (3)0.2255 (4)0.0408 (11)
C151.0604 (4)0.5943 (3)−0.0507 (5)0.0589 (14)
H151.12340.5560−0.03620.071*
C161.1378 (5)0.7305 (4)0.4066 (5)0.0905 (10)
H16A1.21290.70970.40120.109*
H16B1.15130.78010.45780.109*
C171.0136 (4)1.0051 (3)0.3568 (4)0.0621 (15)
H17A0.96251.04010.38740.093*
H17B1.09261.01760.39610.093*
H17C0.99780.94370.36480.093*
C180.9873 (5)0.5992 (3)−0.1572 (5)0.0559 (14)
H181.00210.5661−0.21510.067*
C191.0103 (4)1.1263 (3)0.2207 (4)0.0597 (14)
H19A0.99181.14160.14280.090*
H19B1.08931.14190.25590.090*
H19C0.95981.15760.25590.090*
C201.0817 (5)0.6589 (4)0.4551 (5)0.0905 (10)
C211.0208 (5)0.5970 (4)0.3675 (4)0.0905 (10)
H21A0.97190.55960.39930.109*
H21B1.07850.55930.34890.109*
C221.1532 (5)0.6224 (4)0.5598 (5)0.0905 (10)
H22A1.21210.58510.54430.136*
H22B1.10550.58840.59550.136*
H22C1.18910.66960.60830.136*
C230.9799 (5)0.7069 (4)0.4916 (5)0.0905 (10)
H23A0.93060.66360.51200.136*
H23B0.93540.74160.43030.136*
H23C1.01190.74460.55440.136*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0437 (7)0.0653 (9)0.0458 (8)0.0066 (6)0.0019 (6)−0.0049 (6)
Cl20.0873 (10)0.0793 (10)0.0415 (8)−0.0153 (8)0.0171 (7)−0.0107 (7)
O10.0449 (18)0.0365 (19)0.045 (2)−0.0107 (15)−0.0013 (15)0.0099 (15)
O20.0329 (18)0.050 (2)0.058 (2)0.0001 (17)0.0121 (16)−0.0025 (17)
O30.049 (2)0.0415 (19)0.063 (2)−0.0143 (16)0.0030 (17)0.0017 (16)
O40.044 (2)0.063 (2)0.070 (2)−0.0123 (17)0.0261 (18)−0.0110 (18)
C10.030 (2)0.030 (3)0.031 (2)−0.002 (2)0.0023 (19)0.001 (2)
C20.030 (2)0.031 (3)0.041 (3)−0.006 (2)0.010 (2)−0.005 (2)
C30.026 (2)0.040 (3)0.043 (3)−0.006 (2)0.006 (2)−0.001 (2)
C40.032 (3)0.045 (3)0.039 (3)−0.003 (2)0.003 (2)−0.006 (2)
C50.030 (3)0.042 (3)0.033 (3)−0.001 (2)0.012 (2)0.001 (2)
C60.035 (3)0.040 (3)0.044 (3)−0.004 (2)0.001 (2)0.008 (2)
C70.036 (3)0.035 (3)0.037 (3)−0.003 (2)0.007 (2)0.006 (2)
C80.055 (3)0.050 (3)0.042 (3)−0.020 (3)0.016 (3)−0.005 (3)
C90.039 (3)0.030 (3)0.043 (3)−0.006 (2)0.012 (2)−0.004 (2)
C100.040 (3)0.047 (3)0.048 (3)0.007 (2)0.014 (2)−0.010 (2)
C110.038 (3)0.045 (3)0.061 (3)−0.001 (2)0.015 (2)−0.005 (3)
C120.044 (3)0.035 (3)0.041 (3)−0.003 (2)0.014 (2)−0.005 (2)
C130.051 (3)0.038 (3)0.056 (3)−0.011 (3)0.002 (3)0.007 (2)
C140.037 (3)0.041 (3)0.039 (3)−0.008 (2)0.002 (2)0.003 (2)
C150.052 (3)0.043 (3)0.088 (5)0.008 (2)0.029 (3)−0.001 (3)
C160.098 (2)0.086 (2)0.0683 (19)−0.0274 (16)−0.0119 (15)0.0250 (15)
C170.068 (3)0.074 (4)0.046 (3)−0.017 (3)0.019 (3)−0.012 (3)
C180.067 (4)0.047 (3)0.061 (4)−0.002 (3)0.029 (3)−0.013 (3)
C190.071 (4)0.045 (3)0.067 (4)−0.002 (3)0.026 (3)−0.012 (3)
C200.098 (2)0.086 (2)0.0683 (19)−0.0274 (16)−0.0119 (15)0.0250 (15)
C210.098 (2)0.086 (2)0.0683 (19)−0.0274 (16)−0.0119 (15)0.0250 (15)
C220.098 (2)0.086 (2)0.0683 (19)−0.0274 (16)−0.0119 (15)0.0250 (15)
C230.098 (2)0.086 (2)0.0683 (19)−0.0274 (16)−0.0119 (15)0.0250 (15)

Geometric parameters (Å, °)

Cl1—C91.728 (4)C11—C151.368 (6)
Cl2—C81.729 (5)C11—H110.9300
O1—C61.347 (5)C12—C191.529 (6)
O1—C51.453 (5)C12—C171.532 (6)
O2—C51.388 (5)C13—C141.447 (6)
O2—H220.79 (4)C13—C211.489 (6)
O3—C131.230 (5)C15—C181.379 (6)
O4—C41.209 (5)C15—H150.9300
C1—C31.510 (5)C16—C201.485 (7)
C1—C51.532 (5)C16—H16A0.9700
C1—C41.538 (6)C16—H16B0.9700
C1—H10.9800C17—H17A0.9600
C2—C91.386 (6)C17—H17B0.9600
C2—C111.390 (5)C17—H17C0.9600
C2—C31.529 (6)C18—H180.9300
C3—C141.511 (5)C19—H19A0.9600
C3—H30.9800C19—H19B0.9600
C4—C101.470 (6)C19—H19C0.9600
C5—C71.517 (5)C20—C221.460 (7)
C6—C141.338 (5)C20—C211.473 (7)
C6—C161.488 (6)C20—C231.584 (8)
C7—C121.546 (5)C21—H21A0.9700
C7—H7A0.9700C21—H21B0.9700
C7—H7B0.9700C22—H22A0.9600
C8—C181.364 (6)C22—H22B0.9600
C8—C91.390 (6)C22—H22C0.9600
C10—C121.532 (5)C23—H23A0.9600
C10—H10A0.9700C23—H23B0.9600
C10—H10B0.9700C23—H23C0.9600
C6—O1—C5119.0 (3)C17—C12—C7112.7 (3)
C5—O2—H22106 (3)O3—C13—C14122.5 (4)
C3—C1—C5114.1 (3)O3—C13—C21120.5 (4)
C3—C1—C4112.4 (3)C14—C13—C21116.9 (4)
C5—C1—C4109.2 (3)C6—C14—C13119.2 (4)
C3—C1—H1106.9C6—C14—C3122.5 (4)
C5—C1—H1106.9C13—C14—C3118.3 (4)
C4—C1—H1106.9C11—C15—C18120.8 (5)
C9—C2—C11117.9 (4)C11—C15—H15119.6
C9—C2—C3120.7 (4)C18—C15—H15119.6
C11—C2—C3121.3 (4)C20—C16—C6115.4 (4)
C1—C3—C14108.4 (3)C20—C16—H16A108.4
C1—C3—C2116.3 (3)C6—C16—H16A108.4
C14—C3—C2112.5 (3)C20—C16—H16B108.4
C1—C3—H3106.3C6—C16—H16B108.4
C14—C3—H3106.3H16A—C16—H16B107.5
C2—C3—H3106.3C12—C17—H17A109.5
O4—C4—C10124.2 (4)C12—C17—H17B109.5
O4—C4—C1119.9 (4)H17A—C17—H17B109.5
C10—C4—C1115.8 (4)C12—C17—H17C109.5
O2—C5—O1108.3 (3)H17A—C17—H17C109.5
O2—C5—C7111.5 (3)H17B—C17—H17C109.5
O1—C5—C7104.6 (3)C8—C18—C15119.0 (4)
O2—C5—C1107.8 (3)C8—C18—H18120.5
O1—C5—C1110.6 (3)C15—C18—H18120.5
C7—C5—C1113.9 (3)C12—C19—H19A109.5
C14—C6—O1124.7 (4)C12—C19—H19B109.5
C14—C6—C16124.7 (4)H19A—C19—H19B109.5
O1—C6—C16110.6 (4)C12—C19—H19C109.5
C5—C7—C12117.2 (3)H19A—C19—H19C109.5
C5—C7—H7A108.0H19B—C19—H19C109.5
C12—C7—H7A108.0C22—C20—C21118.2 (5)
C5—C7—H7B108.0C22—C20—C16114.6 (5)
C12—C7—H7B108.0C21—C20—C16110.8 (5)
H7A—C7—H7B107.2C22—C20—C23103.5 (5)
C18—C8—C9120.8 (4)C21—C20—C23103.6 (5)
C18—C8—Cl2118.5 (4)C16—C20—C23104.1 (5)
C9—C8—Cl2120.6 (4)C20—C21—C13117.8 (5)
C2—C9—C8120.4 (4)C20—C21—H21A107.9
C2—C9—Cl1119.7 (3)C13—C21—H21A107.9
C8—C9—Cl1119.8 (4)C20—C21—H21B107.9
C4—C10—C12111.0 (4)C13—C21—H21B107.9
C4—C10—H10A109.4H21A—C21—H21B107.2
C12—C10—H10A109.4C20—C22—H22A109.5
C4—C10—H10B109.4C20—C22—H22B109.5
C12—C10—H10B109.4H22A—C22—H22B109.5
H10A—C10—H10B108.0C20—C22—H22C109.5
C15—C11—C2121.0 (4)H22A—C22—H22C109.5
C15—C11—H11119.5H22B—C22—H22C109.5
C2—C11—H11119.5C20—C23—H23A109.5
C19—C12—C10110.3 (4)C20—C23—H23B109.5
C19—C12—C17108.8 (4)H23A—C23—H23B109.5
C10—C12—C17109.4 (4)C20—C23—H23C109.5
C19—C12—C7108.0 (3)H23A—C23—H23C109.5
C10—C12—C7107.7 (3)H23B—C23—H23C109.5
C5—C1—C3—C1444.4 (5)C1—C4—C10—C12−61.1 (5)
C4—C1—C3—C14−80.6 (4)C9—C2—C11—C15−1.1 (6)
C5—C1—C3—C2−83.6 (4)C3—C2—C11—C15176.0 (4)
C4—C1—C3—C2151.5 (3)C4—C10—C12—C19172.9 (4)
C9—C2—C3—C1−73.9 (5)C4—C10—C12—C17−67.5 (5)
C11—C2—C3—C1109.1 (4)C4—C10—C12—C755.2 (5)
C9—C2—C3—C14160.2 (4)C5—C7—C12—C19−169.0 (4)
C11—C2—C3—C14−16.8 (5)C5—C7—C12—C10−49.8 (5)
C3—C1—C4—O43.8 (5)C5—C7—C12—C1770.8 (5)
C5—C1—C4—O4−123.8 (4)O1—C6—C14—C13−175.9 (4)
C3—C1—C4—C10−179.4 (3)C16—C6—C14—C131.9 (7)
C5—C1—C4—C1053.0 (5)O1—C6—C14—C32.6 (7)
C6—O1—C5—O2−84.3 (4)C16—C6—C14—C3−179.6 (5)
C6—O1—C5—C7156.7 (3)O3—C13—C14—C6174.1 (4)
C6—O1—C5—C133.6 (5)C21—C13—C14—C6−8.4 (7)
C3—C1—C5—O265.9 (4)O3—C13—C14—C3−4.6 (7)
C4—C1—C5—O2−167.5 (3)C21—C13—C14—C3173.0 (5)
C3—C1—C5—O1−52.3 (5)C1—C3—C14—C6−20.3 (6)
C4—C1—C5—O174.3 (4)C2—C3—C14—C6109.8 (5)
C3—C1—C5—C7−169.8 (3)C1—C3—C14—C13158.3 (4)
C4—C1—C5—C7−43.2 (5)C2—C3—C14—C13−71.6 (5)
C5—O1—C6—C14−9.9 (6)C2—C11—C15—C182.2 (7)
C5—O1—C6—C16172.1 (4)C14—C6—C16—C20−17.4 (9)
O2—C5—C7—C12168.1 (3)O1—C6—C16—C20160.6 (5)
O1—C5—C7—C12−75.0 (4)C9—C8—C18—C151.4 (7)
C1—C5—C7—C1245.9 (5)Cl2—C8—C18—C15−179.2 (4)
C11—C2—C9—C80.2 (6)C11—C15—C18—C8−2.3 (7)
C3—C2—C9—C8−176.9 (4)C6—C16—C20—C22174.0 (6)
C11—C2—C9—Cl1178.5 (3)C6—C16—C20—C2137.2 (8)
C3—C2—C9—Cl11.4 (5)C6—C16—C20—C23−73.6 (6)
C18—C8—C9—C2−0.3 (7)C22—C20—C21—C13179.6 (5)
Cl2—C8—C9—C2−179.8 (3)C16—C20—C21—C13−45.3 (8)
C18—C8—C9—Cl1−178.6 (3)C23—C20—C21—C1365.8 (6)
Cl2—C8—C9—Cl11.9 (5)O3—C13—C21—C20−150.8 (5)
O4—C4—C10—C12115.6 (5)C14—C13—C21—C2031.5 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H22···O3i0.79 (4)2.12 (4)2.879 (4)160 (5)

Symmetry codes: (i) x+1/2, −y+3/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2413).

References

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