Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C24H28O4, has been synthesized by the reaction of 5-methyl­salicyl­aldehyde and 5,5-di­methyl-1,3-hexane­dione in water catalyzed by triethyl­benzyl­ammonium chloride. The central pyran ring and outer cyclo­hexene ring of the oxanthene moiety adopt boat and half-chair conformations, respectively. The other cyclo­hexene ring bonded to the pyran moiety has a skew-boat form.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804018276/ob6392sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804018276/ob6392Isup2.hkl
Contains datablock I

CCDC reference: 248855

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.084
  • wR factor = 0.167
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.36
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2000–2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

3,3,7-trimethyl-9-(5,5-dimethyl-3-hydroxy-2-cyclohexene- 1-one-2-yl)-1-oxo-1,2,3,4,9,10-hexahydroxanthene top
Crystal data top
C24H28O4Dx = 1.260 Mg m3
Mr = 380.46Melting point = 491–492 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71070 Å
Hall symbol: -p 2ac 2abCell parameters from 16291 reflections
a = 15.559 (3) Åθ = 3.2–27.5°
b = 11.1768 (19) ŵ = 0.08 mm1
c = 23.057 (4) ÅT = 193 K
V = 4009.7 (11) Å3Platelet, colorless
Z = 80.50 × 0.44 × 0.09 mm
F(000) = 1632
Data collection top
Rigaku Mercury
diffractometer
4586 independent reflections
Radiation source: fine-focus sealed tube4060 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = 2020
Absorption correction: multi-scan
(Jacobson, 1998)
k = 1414
Tmin = 0.959, Tmax = 0.992l = 2925
42649 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.084Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 1.26 w = 1/[σ2(Fo2) + (0.0425P)2 + 3.8447P]
where P = (Fo2 + 2Fc2)/3
4586 reflections(Δ/σ)max < 0.001
263 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.21 e Å3
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
xyzUiso*/Ueq
O10.51809 (11)0.72013 (15)0.46441 (7)0.0299 (4)
O20.33493 (13)1.02752 (16)0.52857 (8)0.0392 (5)
O30.40994 (13)0.94837 (19)0.67231 (8)0.0468 (5)
O40.29587 (12)0.68028 (16)0.53686 (7)0.0322 (4)
C10.53210 (15)0.6742 (2)0.52013 (10)0.0260 (5)
C20.49515 (14)0.7237 (2)0.56866 (11)0.0259 (5)
C30.43668 (14)0.8327 (2)0.56512 (10)0.0249 (5)
H30.46910.90070.58290.030*
C40.42109 (14)0.8661 (2)0.50234 (10)0.0239 (5)
C50.46129 (15)0.8114 (2)0.45790 (10)0.0257 (5)
C60.58321 (16)0.5722 (2)0.52222 (12)0.0318 (6)
H60.60820.54050.48790.038*
C70.59674 (16)0.5185 (2)0.57502 (12)0.0336 (6)
H70.63070.44800.57690.040*
C80.56187 (16)0.5648 (2)0.62598 (11)0.0326 (6)
C90.51201 (16)0.6676 (2)0.62168 (11)0.0317 (6)
H90.48850.70110.65610.038*
C100.36586 (15)0.9666 (2)0.48906 (11)0.0283 (5)
C110.34807 (16)0.9995 (2)0.42653 (11)0.0321 (6)
H11A0.38501.06820.41600.039*
H11B0.28761.02620.42340.039*
C120.36303 (17)0.8990 (2)0.38243 (11)0.0317 (6)
C130.45069 (16)0.8423 (2)0.39541 (10)0.0295 (5)
H13A0.45730.76890.37180.035*
H13B0.49670.89880.38390.035*
C140.35594 (14)0.8162 (2)0.60140 (10)0.0249 (5)
C150.35357 (16)0.8775 (2)0.65712 (11)0.0334 (6)
C160.28197 (18)0.8459 (3)0.69887 (12)0.0413 (7)
H16A0.27310.91420.72560.050*
H16B0.30040.77660.72250.050*
C170.19696 (16)0.8159 (2)0.67026 (11)0.0305 (5)
C180.21112 (16)0.7229 (2)0.62250 (11)0.0311 (6)
H18A0.21450.64270.64060.037*
H18B0.16060.72340.59640.037*
C190.29045 (15)0.7423 (2)0.58674 (10)0.0251 (5)
C200.5775 (2)0.5052 (3)0.68354 (13)0.0451 (7)
H20A0.54830.55040.71420.068*
H20B0.63940.50310.69140.068*
H20C0.55490.42340.68250.068*
C210.29149 (17)0.8051 (2)0.38696 (12)0.0382 (6)
H21A0.28970.77320.42650.057*
H21B0.30300.73980.35960.057*
H21C0.23610.84220.37760.057*
C220.3647 (2)0.9509 (3)0.32117 (13)0.0475 (7)
H22A0.30950.98960.31290.071*
H22B0.37460.88650.29310.071*
H22C0.41101.01000.31820.071*
C230.1325 (2)0.7688 (3)0.71442 (13)0.0481 (8)
H23A0.15610.69750.73340.072*
H23B0.07880.74790.69470.072*
H23C0.12120.83060.74360.072*
C240.1592 (2)0.9305 (2)0.64239 (14)0.0441 (7)
H24A0.15150.99180.67230.066*
H24B0.10350.91190.62470.066*
H24C0.19860.96020.61260.066*
H40.249 (2)0.637 (3)0.5316 (13)0.053 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0322 (9)0.0273 (9)0.0302 (9)0.0094 (7)0.0020 (7)0.0007 (7)
O20.0440 (11)0.0320 (10)0.0415 (11)0.0151 (8)0.0002 (9)0.0076 (8)
O30.0447 (12)0.0581 (13)0.0375 (11)0.0202 (10)0.0026 (9)0.0215 (10)
O40.0341 (10)0.0304 (9)0.0321 (9)0.0094 (8)0.0057 (8)0.0126 (8)
C10.0234 (11)0.0249 (12)0.0296 (12)0.0004 (9)0.0029 (9)0.0001 (10)
C20.0215 (11)0.0242 (12)0.0321 (13)0.0011 (9)0.0033 (9)0.0023 (10)
C30.0222 (11)0.0238 (11)0.0286 (12)0.0007 (9)0.0020 (9)0.0059 (9)
C40.0210 (11)0.0214 (11)0.0291 (12)0.0018 (9)0.0018 (9)0.0021 (9)
C50.0224 (11)0.0213 (11)0.0335 (13)0.0004 (9)0.0007 (9)0.0014 (10)
C60.0280 (13)0.0286 (13)0.0387 (14)0.0054 (10)0.0014 (11)0.0038 (11)
C70.0277 (13)0.0275 (13)0.0457 (15)0.0054 (10)0.0096 (11)0.0001 (11)
C80.0298 (13)0.0295 (13)0.0385 (14)0.0042 (11)0.0098 (11)0.0035 (11)
C90.0297 (13)0.0355 (13)0.0298 (13)0.0013 (11)0.0047 (10)0.0058 (11)
C100.0239 (12)0.0231 (12)0.0378 (14)0.0002 (9)0.0001 (10)0.0050 (10)
C110.0277 (12)0.0268 (12)0.0417 (15)0.0044 (10)0.0015 (11)0.0040 (11)
C120.0336 (13)0.0312 (13)0.0302 (13)0.0037 (11)0.0015 (10)0.0033 (11)
C130.0318 (13)0.0282 (12)0.0286 (13)0.0028 (10)0.0030 (10)0.0010 (10)
C140.0247 (11)0.0229 (11)0.0272 (12)0.0004 (9)0.0011 (9)0.0054 (9)
C150.0306 (13)0.0377 (14)0.0321 (14)0.0038 (11)0.0004 (10)0.0102 (11)
C160.0419 (16)0.0514 (17)0.0306 (14)0.0027 (13)0.0001 (12)0.0089 (13)
C170.0311 (13)0.0335 (13)0.0268 (12)0.0041 (11)0.0021 (10)0.0077 (11)
C180.0315 (13)0.0274 (12)0.0345 (13)0.0042 (10)0.0045 (10)0.0059 (11)
C190.0290 (12)0.0220 (11)0.0242 (11)0.0012 (9)0.0003 (9)0.0038 (9)
C200.0503 (18)0.0427 (16)0.0422 (16)0.0064 (14)0.0168 (14)0.0032 (13)
C210.0357 (14)0.0366 (14)0.0422 (15)0.0012 (12)0.0067 (12)0.0035 (12)
C220.0539 (18)0.0508 (18)0.0378 (16)0.0071 (15)0.0043 (14)0.0113 (14)
C230.0482 (17)0.0562 (19)0.0398 (16)0.0130 (15)0.0141 (13)0.0134 (14)
C240.0444 (17)0.0357 (15)0.0523 (18)0.0047 (13)0.0057 (14)0.0071 (13)
Geometric parameters (Å, º) top
O1—C51.358 (3)C13—H13A0.9900
O1—C11.401 (3)C13—H13B0.9900
O2—C101.235 (3)C14—C191.354 (3)
O3—C151.233 (3)C14—C151.456 (3)
O4—C191.346 (3)C15—C161.514 (4)
O4—H40.88 (4)C16—C171.516 (4)
C1—C21.374 (3)C16—H16A0.9900
C1—C61.390 (3)C16—H16B0.9900
C2—C91.398 (3)C17—C231.523 (4)
C2—C31.523 (3)C17—C181.530 (3)
C3—C41.514 (3)C17—C241.548 (4)
C3—C141.521 (3)C18—C191.500 (3)
C3—H31.0000C18—H18A0.9900
C4—C51.347 (3)C18—H18B0.9900
C4—C101.447 (3)C20—H20A0.9800
C5—C131.491 (3)C20—H20B0.9800
C6—C71.374 (4)C20—H20C0.9800
C6—H60.9500C21—H21A0.9800
C7—C81.394 (4)C21—H21B0.9800
C7—H70.9500C21—H21C0.9800
C8—C91.390 (4)C22—H22A0.9800
C8—C201.505 (4)C22—H22B0.9800
C9—H90.9500C22—H22C0.9800
C10—C111.513 (4)C23—H23A0.9800
C11—C121.533 (4)C23—H23B0.9800
C11—H11A0.9900C23—H23C0.9800
C11—H11B0.9900C24—H24A0.9800
C12—C221.527 (4)C24—H24B0.9800
C12—C131.533 (3)C24—H24C0.9800
C12—C211.533 (4)
C5—O1—C1118.56 (18)C15—C14—C3116.7 (2)
C19—O4—H4111 (2)O3—C15—C14122.3 (2)
C2—C1—C6122.7 (2)O3—C15—C16119.5 (2)
C2—C1—O1122.3 (2)C14—C15—C16118.0 (2)
C6—C1—O1114.9 (2)C15—C16—C17114.6 (2)
C1—C2—C9116.9 (2)C15—C16—H16A108.6
C1—C2—C3121.9 (2)C17—C16—H16A108.6
C9—C2—C3121.2 (2)C15—C16—H16B108.6
C4—C3—C14115.05 (19)C17—C16—H16B108.6
C4—C3—C2110.12 (19)H16A—C16—H16B107.6
C14—C3—C2111.51 (19)C16—C17—C23111.1 (2)
C4—C3—H3106.5C16—C17—C18109.8 (2)
C14—C3—H3106.5C23—C17—C18109.9 (2)
C2—C3—H3106.5C16—C17—C24109.2 (2)
C5—C4—C10117.8 (2)C23—C17—C24108.3 (2)
C5—C4—C3122.8 (2)C18—C17—C24108.5 (2)
C10—C4—C3119.2 (2)C19—C18—C17114.6 (2)
C4—C5—O1124.0 (2)C19—C18—H18A108.6
C4—C5—C13125.3 (2)C17—C18—H18A108.6
O1—C5—C13110.7 (2)C19—C18—H18B108.6
C7—C6—C1118.5 (2)C17—C18—H18B108.6
C7—C6—H6120.8H18A—C18—H18B107.6
C1—C6—H6120.8O4—C19—C14118.7 (2)
C6—C7—C8121.7 (2)O4—C19—C18116.5 (2)
C6—C7—H7119.2C14—C19—C18124.8 (2)
C8—C7—H7119.2C8—C20—H20A109.5
C9—C8—C7117.7 (2)C8—C20—H20B109.5
C9—C8—C20121.3 (2)H20A—C20—H20B109.5
C7—C8—C20121.1 (2)C8—C20—H20C109.5
C8—C9—C2122.5 (2)H20A—C20—H20C109.5
C8—C9—H9118.8H20B—C20—H20C109.5
C2—C9—H9118.8C12—C21—H21A109.5
O2—C10—C4120.2 (2)C12—C21—H21B109.5
O2—C10—C11119.8 (2)H21A—C21—H21B109.5
C4—C10—C11119.9 (2)C12—C21—H21C109.5
C10—C11—C12115.2 (2)H21A—C21—H21C109.5
C10—C11—H11A108.5H21B—C21—H21C109.5
C12—C11—H11A108.5C12—C22—H22A109.5
C10—C11—H11B108.5C12—C22—H22B109.5
C12—C11—H11B108.5H22A—C22—H22B109.5
H11A—C11—H11B107.5C12—C22—H22C109.5
C22—C12—C13108.8 (2)H22A—C22—H22C109.5
C22—C12—C11109.7 (2)H22B—C22—H22C109.5
C13—C12—C11108.0 (2)C17—C23—H23A109.5
C22—C12—C21109.6 (2)C17—C23—H23B109.5
C13—C12—C21110.5 (2)H23A—C23—H23B109.5
C11—C12—C21110.3 (2)C17—C23—H23C109.5
C5—C13—C12112.5 (2)H23A—C23—H23C109.5
C5—C13—H13A109.1H23B—C23—H23C109.5
C12—C13—H13A109.1C17—C24—H24A109.5
C5—C13—H13B109.1C17—C24—H24B109.5
C12—C13—H13B109.1H24A—C24—H24B109.5
H13A—C13—H13B107.8C17—C24—H24C109.5
C19—C14—C15119.2 (2)H24A—C24—H24C109.5
C19—C14—C3124.0 (2)H24B—C24—H24C109.5
C5—O1—C1—C24.7 (3)O2—C10—C11—C12160.7 (2)
C5—O1—C1—C6172.8 (2)C4—C10—C11—C1221.2 (3)
C6—C1—C2—C90.9 (3)C10—C11—C12—C22166.0 (2)
O1—C1—C2—C9178.2 (2)C10—C11—C12—C1347.6 (3)
C6—C1—C2—C3177.7 (2)C10—C11—C12—C2173.2 (3)
O1—C1—C2—C30.4 (3)C4—C5—C13—C1226.7 (3)
C1—C2—C3—C45.2 (3)O1—C5—C13—C12153.8 (2)
C9—C2—C3—C4173.3 (2)C22—C12—C13—C5168.4 (2)
C1—C2—C3—C14134.2 (2)C11—C12—C13—C549.4 (3)
C9—C2—C3—C1444.3 (3)C21—C12—C13—C571.2 (3)
C14—C3—C4—C5132.8 (2)C4—C3—C14—C1953.6 (3)
C2—C3—C4—C55.8 (3)C2—C3—C14—C1972.7 (3)
C14—C3—C4—C1052.0 (3)C4—C3—C14—C15131.2 (2)
C2—C3—C4—C10179.0 (2)C2—C3—C14—C15102.5 (2)
C10—C4—C5—O1176.6 (2)C19—C14—C15—O3177.9 (3)
C3—C4—C5—O11.3 (4)C3—C14—C15—O36.7 (4)
C10—C4—C5—C132.9 (4)C19—C14—C15—C166.1 (4)
C3—C4—C5—C13178.1 (2)C3—C14—C15—C16169.3 (2)
C1—O1—C5—C44.3 (3)O3—C15—C16—C17149.5 (3)
C1—O1—C5—C13176.17 (19)C14—C15—C16—C1734.4 (4)
C2—C1—C6—C70.4 (4)C15—C16—C17—C23172.1 (2)
O1—C1—C6—C7177.1 (2)C15—C16—C17—C1850.3 (3)
C1—C6—C7—C81.1 (4)C15—C16—C17—C2468.5 (3)
C6—C7—C8—C90.4 (4)C16—C17—C18—C1940.4 (3)
C6—C7—C8—C20179.8 (2)C23—C17—C18—C19163.0 (2)
C7—C8—C9—C21.0 (4)C24—C17—C18—C1978.8 (3)
C20—C8—C9—C2178.8 (2)C15—C14—C19—O4175.8 (2)
C1—C2—C9—C81.6 (4)C3—C14—C19—O40.8 (4)
C3—C2—C9—C8177.0 (2)C15—C14—C19—C183.7 (4)
C5—C4—C10—O2172.3 (2)C3—C14—C19—C18178.7 (2)
C3—C4—C10—O23.1 (3)C17—C18—C19—O4165.7 (2)
C5—C4—C10—C115.9 (3)C17—C18—C19—C1414.8 (4)
C3—C4—C10—C11178.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O2i0.88 (4)1.79 (4)2.663 (3)169 (3)
Symmetry code: (i) x+1/2, y1/2, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds