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In the title compound, C15H18O3, the epoxy and furyl rings are planar and inclined to each other by 44.84 (17)°. The α,β-carbonyl system has S-cis conformation and both methyl groups in the ten-membered ring are in axial positions. The mol­ecule is stabilized by van der Waals inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010221/dn2014sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010221/dn2014Isup2.hkl
Contains datablock I

CCDC reference: 605058

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.097
  • Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 1465 Count of symmetry unique reflns 1466 Completeness (_total/calc) 99.93% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

5,9,14-Trimethyl-4,12-dioxa-tricyclo[9.3.0.03,5]tetradeca-1(11),8,13-trien- 2-one top
Crystal data top
C15H18O3Dx = 1.271 Mg m3
Mr = 246.29Melting point: 427 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4030 reflections
a = 9.672 (2) Åθ = 2.5–26.0°
b = 11.414 (3) ŵ = 0.09 mm1
c = 11.656 (3) ÅT = 298 K
V = 1286.7 (5) Å3Block, colourless
Z = 40.45 × 0.40 × 0.40 mm
F(000) = 528
Data collection top
Bruker SMART APEX area-detector
diffractometer
1465 independent reflections
Radiation source: fine-focus sealed tube1374 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 83.66 pixels mm-1θmax = 26.0°, θmin = 2.5°
ω scanh = 1011
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 1413
Tmin = 0.958, Tmax = 0.971l = 1411
7096 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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0637P)2 + 0.0797P]
where P = (Fo2 + 2Fc2)/3
1465 reflections(Δ/σ)max = 0.006
166 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.11 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.24928 (14)0.65309 (14)0.62695 (13)0.0621 (4)
O20.65713 (14)0.59008 (14)0.52543 (13)0.0627 (4)
O30.87601 (16)0.43313 (14)0.53685 (15)0.0670 (4)
C11.2779 (2)0.5632 (2)0.55294 (19)0.0615 (5)
H11.36630.54320.52850.074*
C21.1622 (2)0.50749 (19)0.51999 (17)0.0552 (5)
C31.04958 (19)0.56991 (17)0.57570 (16)0.0481 (4)
C41.10880 (19)0.65876 (18)0.63944 (17)0.0508 (4)
C51.0654 (2)0.75558 (17)0.71650 (19)0.0572 (5)
H5A1.05270.82570.67080.069*
H5B1.13960.77090.77050.069*
C60.9348 (2)0.73302 (15)0.78296 (16)0.0488 (4)
C70.8225 (2)0.79587 (17)0.76167 (17)0.0538 (5)
H70.83530.86450.72010.065*
C80.6769 (2)0.76862 (19)0.79717 (19)0.0597 (5)
H8A0.63100.83920.82350.072*
H8B0.67680.71210.85930.072*
C90.6012 (2)0.71827 (18)0.6925 (2)0.0586 (5)
H9A0.50650.70050.71340.070*
H9B0.59910.77680.63210.070*
C100.66979 (19)0.60867 (17)0.64762 (16)0.0499 (4)
C110.78984 (18)0.62309 (17)0.56959 (16)0.0492 (4)
H110.81770.70420.55450.059*
C120.90320 (19)0.53363 (17)0.56105 (15)0.0481 (4)
C131.1541 (2)0.4075 (2)0.4392 (2)0.0736 (7)
H13A1.10920.43220.36980.110*
H13B1.10220.34510.47370.110*
H13C1.24570.38050.42180.110*
C140.9438 (2)0.63585 (19)0.86952 (19)0.0624 (5)
H14A0.85520.62520.90520.094*
H14B1.01100.65560.92690.094*
H14C0.97080.56470.83180.094*
C150.6513 (2)0.49939 (17)0.7177 (2)0.0622 (5)
H15A0.55440.48450.72840.093*
H15B0.69480.50950.79110.093*
H15C0.69280.43430.67850.093*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0423 (7)0.0733 (9)0.0706 (9)0.0105 (7)0.0017 (7)0.0108 (8)
O20.0520 (8)0.0773 (10)0.0590 (8)0.0032 (7)0.0208 (7)0.0078 (7)
O30.0545 (8)0.0644 (9)0.0822 (10)0.0039 (7)0.0008 (7)0.0221 (8)
C10.0433 (10)0.0756 (13)0.0655 (13)0.0060 (9)0.0046 (10)0.0142 (11)
C20.0480 (9)0.0678 (12)0.0498 (9)0.0082 (10)0.0006 (9)0.0118 (9)
C30.0466 (9)0.0555 (10)0.0421 (8)0.0005 (8)0.0013 (8)0.0076 (8)
C40.0408 (9)0.0583 (10)0.0533 (10)0.0090 (8)0.0006 (8)0.0110 (9)
C50.0552 (12)0.0527 (10)0.0636 (12)0.0149 (9)0.0040 (10)0.0007 (10)
C60.0513 (10)0.0459 (9)0.0494 (10)0.0076 (8)0.0066 (8)0.0009 (8)
C70.0600 (11)0.0434 (8)0.0579 (10)0.0034 (9)0.0091 (10)0.0015 (8)
C80.0524 (10)0.0565 (11)0.0704 (12)0.0104 (9)0.0090 (10)0.0068 (9)
C90.0447 (10)0.0585 (11)0.0728 (13)0.0067 (9)0.0115 (10)0.0008 (10)
C100.0378 (8)0.0554 (10)0.0566 (10)0.0009 (8)0.0111 (8)0.0017 (8)
C110.0464 (10)0.0542 (10)0.0471 (9)0.0018 (8)0.0113 (8)0.0022 (8)
C120.0470 (9)0.0560 (11)0.0414 (9)0.0032 (8)0.0008 (8)0.0023 (8)
C130.0586 (13)0.0949 (17)0.0673 (13)0.0184 (13)0.0041 (11)0.0125 (13)
C140.0521 (11)0.0720 (13)0.0631 (12)0.0048 (10)0.0010 (10)0.0147 (11)
C150.0495 (10)0.0564 (11)0.0809 (14)0.0041 (9)0.0059 (10)0.0025 (10)
Geometric parameters (Å, º) top
O1—C41.368 (2)C8—C91.535 (3)
O1—C11.369 (3)C8—H8A0.9700
O2—C111.433 (2)C8—H8B0.9700
O2—C101.445 (2)C9—C101.509 (3)
O3—C121.210 (2)C9—H9A0.9700
C1—C21.343 (3)C9—H9B0.9700
C1—H10.9300C10—C111.484 (3)
C2—C31.455 (3)C10—C151.502 (3)
C2—C131.482 (3)C11—C121.502 (3)
C3—C41.381 (3)C11—H110.9800
C3—C121.485 (3)C13—H13A0.9600
C4—C51.485 (3)C13—H13B0.9600
C5—C61.504 (3)C13—H13C0.9600
C5—H5A0.9700C14—H14A0.9600
C5—H5B0.9700C14—H14B0.9600
C6—C71.326 (3)C14—H14C0.9600
C6—C141.502 (3)C15—H15A0.9600
C7—C81.500 (3)C15—H15B0.9600
C7—H70.9300C15—H15C0.9600
C4—O1—C1107.65 (17)C8—C9—H9B109.2
C11—O2—C1062.07 (12)H9A—C9—H9B107.9
C2—C1—O1111.53 (18)O2—C10—C1158.58 (11)
C2—C1—H1124.2O2—C10—C15113.85 (17)
O1—C1—H1124.2C11—C10—C15121.25 (17)
C1—C2—C3105.31 (19)O2—C10—C9115.20 (17)
C1—C2—C13126.19 (19)C11—C10—C9117.66 (18)
C3—C2—C13128.43 (19)C15—C10—C9116.58 (18)
C4—C3—C2106.80 (17)O2—C11—C1059.35 (12)
C4—C3—C12131.45 (18)O2—C11—C12116.83 (16)
C2—C3—C12121.74 (17)C10—C11—C12122.45 (17)
O1—C4—C3108.66 (19)O2—C11—H11115.5
O1—C4—C5112.35 (18)C10—C11—H11115.5
C3—C4—C5138.99 (18)C12—C11—H11115.5
C4—C5—C6114.93 (16)O3—C12—C3119.89 (18)
C4—C5—H5A108.5O3—C12—C11120.09 (18)
C6—C5—H5A108.5C3—C12—C11119.93 (16)
C4—C5—H5B108.5C2—C13—H13A109.5
C6—C5—H5B108.5C2—C13—H13B109.5
H5A—C5—H5B107.5H13A—C13—H13B109.5
C7—C6—C14124.93 (19)C2—C13—H13C109.5
C7—C6—C5119.97 (18)H13A—C13—H13C109.5
C14—C6—C5115.10 (17)H13B—C13—H13C109.5
C6—C7—C8127.27 (19)C6—C14—H14A109.5
C6—C7—H7116.4C6—C14—H14B109.5
C8—C7—H7116.4H14A—C14—H14B109.5
C7—C8—C9107.82 (18)C6—C14—H14C109.5
C7—C8—H8A110.1H14A—C14—H14C109.5
C9—C8—H8A110.1H14B—C14—H14C109.5
C7—C8—H8B110.1C10—C15—H15A109.5
C9—C8—H8B110.1C10—C15—H15B109.5
H8A—C8—H8B108.5H15A—C15—H15B109.5
C10—C9—C8112.10 (17)C10—C15—H15C109.5
C10—C9—H9A109.2H15A—C15—H15C109.5
C8—C9—H9A109.2H15B—C15—H15C109.5
C10—C9—H9B109.2
 

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