5,9,14-Trimethyl-4,12-dioxa­tricyclo­[9.3.0.0^3,5]tetra­deca-1(11),8,13-trien-2-one (zederone)

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.

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

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[9.3.0.0^3,5]tetradeca-1(11),8,13-trien- 2-one

Crystal data

C15H18O3	Dx = 1.271 Mg m^−3
Mr = 246.29	Melting point: 427 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4030 reflections
a = 9.672 (2) Å	θ = 2.5–26.0°
b = 11.414 (3) Å	µ = 0.09 mm^−1
c = 11.656 (3) Å	T = 298 K
V = 1286.7 (5) Å^3	Block, colourless
Z = 4	0.45 × 0.40 × 0.40 mm
F(000) = 528

Data collection

Bruker SMART APEX area-detector diffractometer	1465 independent reflections
Radiation source: fine-focus sealed tube	1374 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 83.66 pixels mm^-1	θmax = 26.0°, θmin = 2.5°
ω scan	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −14→13
Tmin = 0.958, Tmax = 0.971	l = −14→11
7096 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0637P)^2 + 0.0797P] where P = (Fo^2 + 2Fc^2)/3
1465 reflections	(Δ/σ)max = 0.006
166 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.11 e Å^−3

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	1.24928 (14)	0.65309 (14)	0.62695 (13)	0.0621 (4)
O2	0.65713 (14)	0.59008 (14)	0.52543 (13)	0.0627 (4)
O3	0.87601 (16)	0.43313 (14)	0.53685 (15)	0.0670 (4)
C1	1.2779 (2)	0.5632 (2)	0.55294 (19)	0.0615 (5)
H1	1.3663	0.5432	0.5285	0.074*
C2	1.1622 (2)	0.50749 (19)	0.51999 (17)	0.0552 (5)
C3	1.04958 (19)	0.56991 (17)	0.57570 (16)	0.0481 (4)
C4	1.10880 (19)	0.65876 (18)	0.63944 (17)	0.0508 (4)
C5	1.0654 (2)	0.75558 (17)	0.71650 (19)	0.0572 (5)
H5A	1.0527	0.8257	0.6708	0.069*
H5B	1.1396	0.7709	0.7705	0.069*
C6	0.9348 (2)	0.73302 (15)	0.78296 (16)	0.0488 (4)
C7	0.8225 (2)	0.79587 (17)	0.76167 (17)	0.0538 (5)
H7	0.8353	0.8645	0.7201	0.065*
C8	0.6769 (2)	0.76862 (19)	0.79717 (19)	0.0597 (5)
H8A	0.6310	0.8392	0.8235	0.072*
H8B	0.6768	0.7121	0.8593	0.072*
C9	0.6012 (2)	0.71827 (18)	0.6925 (2)	0.0586 (5)
H9A	0.5065	0.7005	0.7134	0.070*
H9B	0.5991	0.7768	0.6321	0.070*
C10	0.66979 (19)	0.60867 (17)	0.64762 (16)	0.0499 (4)
C11	0.78984 (18)	0.62309 (17)	0.56959 (16)	0.0492 (4)
H11	0.8177	0.7042	0.5545	0.059*
C12	0.90320 (19)	0.53363 (17)	0.56105 (15)	0.0481 (4)
C13	1.1541 (2)	0.4075 (2)	0.4392 (2)	0.0736 (7)
H13A	1.1092	0.4322	0.3698	0.110*
H13B	1.1022	0.3451	0.4737	0.110*
H13C	1.2457	0.3805	0.4218	0.110*
C14	0.9438 (2)	0.63585 (19)	0.86952 (19)	0.0624 (5)
H14A	0.8552	0.6252	0.9052	0.094*
H14B	1.0110	0.6556	0.9269	0.094*
H14C	0.9708	0.5647	0.8318	0.094*
C15	0.6513 (2)	0.49939 (17)	0.7177 (2)	0.0622 (5)
H15A	0.5544	0.4845	0.7284	0.093*
H15B	0.6948	0.5095	0.7911	0.093*
H15C	0.6928	0.4343	0.6785	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0423 (7)	0.0733 (9)	0.0706 (9)	−0.0105 (7)	−0.0017 (7)	0.0108 (8)
O2	0.0520 (8)	0.0773 (10)	0.0590 (8)	0.0032 (7)	−0.0208 (7)	−0.0078 (7)
O3	0.0545 (8)	0.0644 (9)	0.0822 (10)	−0.0039 (7)	0.0008 (7)	−0.0221 (8)
C1	0.0433 (10)	0.0756 (13)	0.0655 (13)	0.0060 (9)	0.0046 (10)	0.0142 (11)
C2	0.0480 (9)	0.0678 (12)	0.0498 (9)	0.0082 (10)	−0.0006 (9)	0.0118 (9)
C3	0.0466 (9)	0.0555 (10)	0.0421 (8)	−0.0005 (8)	0.0013 (8)	0.0076 (8)
C4	0.0408 (9)	0.0583 (10)	0.0533 (10)	−0.0090 (8)	−0.0006 (8)	0.0110 (9)
C5	0.0552 (12)	0.0527 (10)	0.0636 (12)	−0.0149 (9)	−0.0040 (10)	0.0007 (10)
C6	0.0513 (10)	0.0459 (9)	0.0494 (10)	−0.0076 (8)	−0.0066 (8)	−0.0009 (8)
C7	0.0600 (11)	0.0434 (8)	0.0579 (10)	−0.0034 (9)	−0.0091 (10)	−0.0015 (8)
C8	0.0524 (10)	0.0565 (11)	0.0704 (12)	0.0104 (9)	−0.0090 (10)	−0.0068 (9)
C9	0.0447 (10)	0.0585 (11)	0.0728 (13)	0.0067 (9)	−0.0115 (10)	−0.0008 (10)
C10	0.0378 (8)	0.0554 (10)	0.0566 (10)	−0.0009 (8)	−0.0111 (8)	−0.0017 (8)
C11	0.0464 (10)	0.0542 (10)	0.0471 (9)	−0.0018 (8)	−0.0113 (8)	0.0022 (8)
C12	0.0470 (9)	0.0560 (11)	0.0414 (9)	−0.0032 (8)	−0.0008 (8)	−0.0023 (8)
C13	0.0586 (13)	0.0949 (17)	0.0673 (13)	0.0184 (13)	0.0041 (11)	−0.0125 (13)
C14	0.0521 (11)	0.0720 (13)	0.0631 (12)	0.0048 (10)	−0.0010 (10)	0.0147 (11)
C15	0.0495 (10)	0.0564 (11)	0.0809 (14)	−0.0041 (9)	0.0059 (10)	0.0025 (10)

Geometric parameters (Å, º)

O1—C4	1.368 (2)	C8—C9	1.535 (3)
O1—C1	1.369 (3)	C8—H8A	0.9700
O2—C11	1.433 (2)	C8—H8B	0.9700
O2—C10	1.445 (2)	C9—C10	1.509 (3)
O3—C12	1.210 (2)	C9—H9A	0.9700
C1—C2	1.343 (3)	C9—H9B	0.9700
C1—H1	0.9300	C10—C11	1.484 (3)
C2—C3	1.455 (3)	C10—C15	1.502 (3)
C2—C13	1.482 (3)	C11—C12	1.502 (3)
C3—C4	1.381 (3)	C11—H11	0.9800
C3—C12	1.485 (3)	C13—H13A	0.9600
C4—C5	1.485 (3)	C13—H13B	0.9600
C5—C6	1.504 (3)	C13—H13C	0.9600
C5—H5A	0.9700	C14—H14A	0.9600
C5—H5B	0.9700	C14—H14B	0.9600
C6—C7	1.326 (3)	C14—H14C	0.9600
C6—C14	1.502 (3)	C15—H15A	0.9600
C7—C8	1.500 (3)	C15—H15B	0.9600
C7—H7	0.9300	C15—H15C	0.9600
C4—O1—C1	107.65 (17)	C8—C9—H9B	109.2
C11—O2—C10	62.07 (12)	H9A—C9—H9B	107.9
C2—C1—O1	111.53 (18)	O2—C10—C11	58.58 (11)
C2—C1—H1	124.2	O2—C10—C15	113.85 (17)
O1—C1—H1	124.2	C11—C10—C15	121.25 (17)
C1—C2—C3	105.31 (19)	O2—C10—C9	115.20 (17)
C1—C2—C13	126.19 (19)	C11—C10—C9	117.66 (18)
C3—C2—C13	128.43 (19)	C15—C10—C9	116.58 (18)
C4—C3—C2	106.80 (17)	O2—C11—C10	59.35 (12)
C4—C3—C12	131.45 (18)	O2—C11—C12	116.83 (16)
C2—C3—C12	121.74 (17)	C10—C11—C12	122.45 (17)
O1—C4—C3	108.66 (19)	O2—C11—H11	115.5
O1—C4—C5	112.35 (18)	C10—C11—H11	115.5
C3—C4—C5	138.99 (18)	C12—C11—H11	115.5
C4—C5—C6	114.93 (16)	O3—C12—C3	119.89 (18)
C4—C5—H5A	108.5	O3—C12—C11	120.09 (18)
C6—C5—H5A	108.5	C3—C12—C11	119.93 (16)
C4—C5—H5B	108.5	C2—C13—H13A	109.5
C6—C5—H5B	108.5	C2—C13—H13B	109.5
H5A—C5—H5B	107.5	H13A—C13—H13B	109.5
C7—C6—C14	124.93 (19)	C2—C13—H13C	109.5
C7—C6—C5	119.97 (18)	H13A—C13—H13C	109.5
C14—C6—C5	115.10 (17)	H13B—C13—H13C	109.5
C6—C7—C8	127.27 (19)	C6—C14—H14A	109.5
C6—C7—H7	116.4	C6—C14—H14B	109.5
C8—C7—H7	116.4	H14A—C14—H14B	109.5
C7—C8—C9	107.82 (18)	C6—C14—H14C	109.5
C7—C8—H8A	110.1	H14A—C14—H14C	109.5
C9—C8—H8A	110.1	H14B—C14—H14C	109.5
C7—C8—H8B	110.1	C10—C15—H15A	109.5
C9—C8—H8B	110.1	C10—C15—H15B	109.5
H8A—C8—H8B	108.5	H15A—C15—H15B	109.5
C10—C9—C8	112.10 (17)	C10—C15—H15C	109.5
C10—C9—H9A	109.2	H15A—C15—H15C	109.5
C8—C9—H9A	109.2	H15B—C15—H15C	109.5
C10—C9—H9B	109.2