7,7-Dimethyl-3,3,4a-tris-(3-methyl-but-2-en-yl)-4a,5,6,7-tetra-hydro-2H-chromene-2,4(3H)-dione.

The title compound, C(26)H(38)O(3), was prepared by an intra-molecular Claisen-like cyclization of ethyl 2-acet-oxy-4,4-dimethyl-1-(3-methyl-but-2-en-yl)cyclo-hex-2-enecarboxyl-ate followed by dialkyl-ation. One of the methyl groups is disordered over two sets of sites in a 0.67:0.33 ratio.

Related literature

For further information, see: Ciochina & Grossman (2006 ▶).

Experimental

Crystal data

C26H38O3

M = 398.56

Triclinic,

a = 9.534 (2) Å

b = 11.753 (3) Å

c = 11.994 (2) Å

α = 77.862 (13)°

β = 78.325 (12)°

γ = 66.427 (9)°

V = 1193.7 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 173 K

0.50 × 0.27 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

14072 measured reflections

4134 independent reflections

1323 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.112

S = 1.02

4134 reflections

280 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.10 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025021/hb5012sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025021/hb5012Isup2.hkl

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

C26H38O3	Z = 2
Mr = 398.56	F(000) = 436
Triclinic, P1	Dx = 1.109 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.534 (2) Å	Cell parameters from 14072 reflections
b = 11.753 (3) Å	θ = 3.1–25.0°
c = 11.994 (2) Å	µ = 0.07 mm−1
α = 77.862 (13)°	T = 173 K
β = 78.325 (12)°	Block, light yellow
γ = 66.427 (9)°	0.50 × 0.27 × 0.04 mm
V = 1193.7 (5) Å3

Nonius KappaCCD diffractometer	1323 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.078
graphite	θmax = 25.0°, θmin = 3.1°
Detector resolution: 19 vertical, 18 horizontal pixels mm-1	h = −11→11
415 frames via ω–rotation (Δω = 2%) and two times 20 s per frame (four sets at different κ–angles) scans	k = −12→13
14072 measured reflections	l = −13→14
4134 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.02	w = {exp[6.80(sinθ/λ)2]}/[σ2(Fo2)]
4134 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.10 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.4586 (2)	0.12777 (19)	−0.11632 (17)	0.0438 (6)
O2	0.2943 (3)	0.5220 (2)	0.00396 (18)	0.0507 (6)
O3	0.1723 (2)	0.3951 (2)	0.08269 (17)	0.0443 (6)
C1	0.4204 (4)	0.3126 (3)	−0.0442 (2)	0.0372 (8)
C2	0.3690 (4)	0.2119 (3)	−0.0635 (2)	0.0386 (8)
C3	0.2036 (3)	0.2213 (3)	−0.0182 (3)	0.0394 (8)
C4	0.1504 (4)	0.2817 (3)	0.0889 (3)	0.0392 (8)
C6	0.2921 (4)	0.4184 (3)	0.0126 (3)	0.0426 (9)
C7	0.1940 (4)	0.0910 (3)	0.0104 (3)	0.0472 (9)
H7A	0.2001	0.0604	−0.0620	0.057*
H7B	0.2831	0.0320	0.0498	0.057*
C8	0.0452 (4)	0.0929 (3)	0.0869 (3)	0.0530 (10)
H8A	0.0406	0.0085	0.0988	0.064*
H8B	−0.0438	0.1524	0.0476	0.064*
C9	0.0324 (4)	0.1315 (3)	0.2045 (3)	0.0510 (9)
C10	0.0782 (4)	0.2443 (3)	0.1852 (3)	0.0443 (8)
H10A	0.0527	0.2909	0.2471	0.053*
C11	0.4951 (4)	0.3655 (3)	−0.1577 (2)	0.0455 (9)
H11A	0.5402	0.4215	−0.1405	0.055*
H11B	0.5809	0.2949	−0.1908	0.055*
C12	0.3886 (4)	0.4374 (3)	−0.2471 (3)	0.0474 (9)
H12A	0.3095	0.5145	−0.2298	0.057*
C13	0.3937 (4)	0.4043 (3)	−0.3474 (3)	0.0541 (10)
C14	0.5093 (4)	0.2854 (3)	−0.3914 (3)	0.0681 (12)
H14A	0.5716	0.2319	−0.3308	0.102*
H14B	0.5769	0.3068	−0.4585	0.102*
H14C	0.4543	0.2404	−0.4135	0.102*
C15	0.2786 (4)	0.4871 (3)	−0.4286 (3)	0.0691 (12)
H15A	0.2106	0.5635	−0.3958	0.104*
H15B	0.2168	0.4420	−0.4400	0.104*
H15C	0.3338	0.5097	−0.5027	0.104*
C21	0.5472 (3)	0.2483 (3)	0.0391 (2)	0.0411 (8)
H21A	0.6433	0.1969	−0.0051	0.049*
H21B	0.5685	0.3152	0.0624	0.049*
C22	0.5124 (3)	0.1669 (3)	0.1455 (3)	0.0399 (8)
H22A	0.5189	0.0868	0.1354	0.048*
C23	0.4738 (4)	0.1926 (3)	0.2516 (3)	0.0417 (8)
C24	0.4434 (4)	0.3177 (3)	0.2852 (3)	0.0564 (10)
H24A	0.4566	0.3760	0.2161	0.085*
H24B	0.5163	0.3071	0.3372	0.085*
H24C	0.3376	0.3513	0.3242	0.085*
C25	0.4543 (4)	0.0965 (3)	0.3513 (3)	0.0584 (10)
H25A	0.4790	0.0171	0.3236	0.088*
H25B	0.3473	0.1258	0.3888	0.088*
H25C	0.5239	0.0839	0.4066	0.088*
C31	0.1015 (4)	0.3067 (3)	−0.1133 (2)	0.0476 (9)
H31A	−0.0082	0.3225	−0.0828	0.057*
H31B	0.1141	0.3885	−0.1306	0.057*
C32	0.1389 (4)	0.2524 (3)	−0.2233 (3)	0.0529 (10)
H32A	0.2407	0.1933	−0.2390	0.064*
C33	0.0465 (4)	0.2776 (3)	−0.2995 (3)	0.0473 (9)
C34	0.0995 (4)	0.2205 (3)	−0.4097 (3)	0.0587 (10)
H34A	0.2051	0.1584	−0.4084	0.088*
H34B	0.0970	0.2866	−0.4754	0.088*
H34C	0.0307	0.1795	−0.4166	0.088*
C35	−0.1086 (10)	0.3876 (7)	−0.2954 (8)	0.060 (2)	0.67
H35A	−0.1338	0.4175	−0.2207	0.091*	0.67
H35B	−0.1890	0.3602	−0.3059	0.091*	0.67
H35C	−0.1025	0.4557	−0.3569	0.091*	0.67
C35'	−0.124 (2)	0.3261 (15)	−0.273 (2)	0.074 (6)	0.33
H35D	−0.1603	0.2575	−0.2658	0.111*	0.33
H35E	−0.1692	0.3918	−0.3352	0.111*	0.33
H35F	−0.1550	0.3610	−0.2005	0.111*	0.33
C41	−0.1364 (4)	0.1687 (4)	0.2621 (3)	0.0694 (11)
H41A	−0.1462	0.1968	0.3357	0.104*
H41B	−0.1669	0.0961	0.2756	0.104*
H41C	−0.2035	0.2369	0.2117	0.104*
C42	0.1373 (4)	0.0236 (3)	0.2825 (3)	0.0659 (11)
H42A	0.2441	−0.0021	0.2444	0.099*
H42B	0.1039	−0.0475	0.2974	0.099*
H42C	0.1311	0.0515	0.3554	0.099*

	U11	U22	U33	U12	U13	U23
O1	0.0398 (14)	0.0366 (14)	0.0521 (14)	−0.0077 (11)	−0.0051 (11)	−0.0148 (11)
O2	0.0497 (15)	0.0371 (15)	0.0653 (16)	−0.0125 (12)	−0.0087 (12)	−0.0139 (12)
O3	0.0433 (15)	0.0355 (14)	0.0523 (14)	−0.0116 (12)	−0.0008 (12)	−0.0143 (11)
C1	0.038 (2)	0.036 (2)	0.0391 (18)	−0.0108 (17)	−0.0070 (16)	−0.0122 (16)
C2	0.044 (2)	0.034 (2)	0.0362 (19)	−0.0085 (18)	−0.0121 (16)	−0.0057 (16)
C3	0.035 (2)	0.036 (2)	0.0446 (19)	−0.0058 (17)	−0.0098 (16)	−0.0094 (16)
C4	0.037 (2)	0.033 (2)	0.048 (2)	−0.0101 (17)	−0.0093 (17)	−0.0093 (17)
C6	0.044 (2)	0.037 (2)	0.048 (2)	−0.0129 (18)	−0.0111 (18)	−0.0096 (17)
C7	0.040 (2)	0.040 (2)	0.064 (2)	−0.0118 (17)	−0.0118 (18)	−0.0128 (18)
C8	0.040 (2)	0.047 (2)	0.077 (3)	−0.0190 (18)	−0.0073 (19)	−0.015 (2)
C9	0.039 (2)	0.053 (2)	0.066 (2)	−0.0235 (19)	−0.0032 (19)	−0.010 (2)
C10	0.036 (2)	0.046 (2)	0.046 (2)	−0.0101 (17)	−0.0059 (17)	−0.0082 (17)
C11	0.049 (2)	0.040 (2)	0.047 (2)	−0.0147 (18)	−0.0057 (17)	−0.0087 (17)
C12	0.058 (2)	0.036 (2)	0.046 (2)	−0.0153 (18)	−0.0088 (18)	−0.0029 (17)
C13	0.073 (3)	0.048 (2)	0.046 (2)	−0.028 (2)	−0.0129 (19)	−0.0014 (18)
C14	0.092 (3)	0.059 (3)	0.053 (2)	−0.025 (2)	−0.008 (2)	−0.017 (2)
C15	0.093 (3)	0.062 (3)	0.054 (2)	−0.026 (2)	−0.031 (2)	0.004 (2)
C21	0.036 (2)	0.042 (2)	0.046 (2)	−0.0108 (17)	−0.0068 (16)	−0.0115 (17)
C22	0.037 (2)	0.035 (2)	0.045 (2)	−0.0099 (16)	−0.0079 (16)	−0.0056 (17)
C23	0.039 (2)	0.041 (2)	0.043 (2)	−0.0098 (17)	−0.0073 (16)	−0.0086 (17)
C24	0.065 (3)	0.054 (2)	0.051 (2)	−0.019 (2)	−0.0064 (19)	−0.0158 (18)
C25	0.063 (3)	0.058 (3)	0.051 (2)	−0.019 (2)	−0.0108 (19)	−0.0045 (19)
C31	0.040 (2)	0.048 (2)	0.051 (2)	−0.0079 (17)	−0.0101 (17)	−0.0118 (18)
C32	0.036 (2)	0.064 (3)	0.053 (2)	−0.0066 (18)	−0.0073 (18)	−0.0204 (19)
C33	0.040 (2)	0.054 (2)	0.049 (2)	−0.0168 (18)	−0.0026 (17)	−0.0143 (18)
C34	0.058 (3)	0.066 (3)	0.052 (2)	−0.021 (2)	−0.0042 (19)	−0.016 (2)
C35	0.051 (5)	0.072 (7)	0.054 (4)	−0.009 (5)	−0.016 (3)	−0.018 (5)
C35'	0.055 (10)	0.060 (13)	0.120 (17)	−0.015 (10)	−0.024 (9)	−0.043 (12)
C41	0.053 (3)	0.076 (3)	0.089 (3)	−0.034 (2)	0.005 (2)	−0.025 (2)
C42	0.061 (3)	0.060 (3)	0.072 (3)	−0.024 (2)	−0.010 (2)	0.006 (2)

O1—C2	1.216 (3)	C21—C22	1.491 (4)
O2—C6	1.207 (3)	C21—H21A	0.9900
O3—C6	1.361 (4)	C21—H21B	0.9900
O3—C4	1.413 (3)	C22—C23	1.316 (4)
C1—C2	1.523 (4)	C22—H22A	0.9500
C1—C6	1.519 (4)	C23—C25	1.499 (4)
C1—C11	1.534 (4)	C23—C24	1.506 (4)
C1—C21	1.572 (4)	C24—H24A	0.9800
C2—C3	1.527 (4)	C24—H24B	0.9800
C3—C4	1.498 (4)	C24—H24C	0.9800
C3—C7	1.533 (4)	C25—H25A	0.9800
C3—C31	1.563 (4)	C25—H25B	0.9800
C4—C10	1.307 (4)	C25—H25C	0.9800
C7—C8	1.520 (4)	C31—C32	1.502 (4)
C7—H7A	0.9900	C31—H31A	0.9900
C7—H7B	0.9900	C31—H31B	0.9900
C8—C9	1.539 (4)	C32—C33	1.305 (4)
C8—H8A	0.9900	C32—H32A	0.9500
C8—H8B	0.9900	C33—C35	1.526 (9)
C9—C10	1.514 (4)	C33—C34	1.511 (4)
C9—C42	1.532 (4)	C33—C35'	1.48 (2)
C9—C41	1.541 (4)	C34—H34A	0.9800
C10—H10A	0.9500	C34—H34B	0.9800
C11—C12	1.506 (4)	C34—H34C	0.9800
C11—H11A	0.9900	C35—H35A	0.9800
C11—H11B	0.9900	C35—H35B	0.9800
C12—C13	1.327 (4)	C35—H35C	0.9800
C12—H12A	0.9500	C35'—H35D	0.9800
C13—C15	1.510 (4)	C35'—H35E	0.9800
C13—C14	1.513 (5)	C35'—H35F	0.9800
C14—H14A	0.9800	C41—H41A	0.9800
C14—H14B	0.9800	C41—H41B	0.9800
C14—H14C	0.9800	C41—H41C	0.9800
C15—H15A	0.9800	C42—H42A	0.9800
C15—H15B	0.9800	C42—H42B	0.9800
C15—H15C	0.9800	C42—H42C	0.9800
C6—O3—C4	121.5 (3)	H15B—C15—H15C	109.5
C2—C1—C6	113.8 (3)	C22—C21—C1	117.3 (3)
C2—C1—C11	110.5 (2)	C22—C21—H21A	108.0
C6—C1—C11	110.3 (3)	C1—C21—H21A	108.0
C2—C1—C21	107.5 (2)	C22—C21—H21B	108.0
C6—C1—C21	106.9 (2)	C1—C21—H21B	108.0
C11—C1—C21	107.5 (2)	H21A—C21—H21B	107.2
O1—C2—C1	119.7 (3)	C23—C22—C21	127.8 (3)
O1—C2—C3	121.5 (3)	C23—C22—H22A	116.1
C1—C2—C3	118.8 (3)	C21—C22—H22A	116.1
C4—C3—C2	109.1 (2)	C22—C23—C25	121.5 (3)
C4—C3—C7	108.7 (3)	C22—C23—C24	124.6 (3)
C2—C3—C7	110.9 (2)	C25—C23—C24	113.9 (3)
C4—C3—C31	109.3 (2)	C23—C24—H24A	109.5
C2—C3—C31	106.9 (3)	C23—C24—H24B	109.5
C7—C3—C31	111.7 (2)	H24A—C24—H24B	109.5
C10—C4—O3	116.7 (3)	C23—C24—H24C	109.5
C10—C4—C3	126.7 (3)	H24A—C24—H24C	109.5
O3—C4—C3	116.5 (3)	H24B—C24—H24C	109.5
O2—C6—O3	117.3 (3)	C23—C25—H25A	109.5
O2—C6—C1	123.3 (3)	C23—C25—H25B	109.5
O3—C6—C1	119.2 (3)	H25A—C25—H25B	109.5
C8—C7—C3	111.9 (3)	C23—C25—H25C	109.5
C8—C7—H7A	109.2	H25A—C25—H25C	109.5
C3—C7—H7A	109.2	H25B—C25—H25C	109.5
C8—C7—H7B	109.2	C32—C31—C3	114.1 (3)
C3—C7—H7B	109.2	C32—C31—H31A	108.7
H7A—C7—H7B	107.9	C3—C31—H31A	108.7
C7—C8—C9	112.3 (2)	C32—C31—H31B	108.7
C7—C8—H8A	109.2	C3—C31—H31B	108.7
C9—C8—H8A	109.2	H31A—C31—H31B	107.6
C7—C8—H8B	109.2	C33—C32—C31	127.0 (3)
C9—C8—H8B	109.2	C33—C32—H32A	116.5
H8A—C8—H8B	107.9	C31—C32—H32A	116.5
C10—C9—C42	110.0 (3)	C32—C33—C35	121.1 (4)
C10—C9—C41	108.8 (3)	C32—C33—C34	122.2 (3)
C42—C9—C41	109.6 (3)	C35—C33—C34	115.4 (4)
C10—C9—C8	108.4 (3)	C32—C33—C35'	123.6 (9)
C42—C9—C8	110.9 (3)	C34—C33—C35'	111.2 (8)
C41—C9—C8	109.1 (3)	C33—C34—H34A	109.5
C4—C10—C9	124.3 (3)	C33—C34—H34B	109.5
C4—C10—H10A	117.8	H34A—C34—H34B	109.5
C9—C10—H10A	117.8	C33—C34—H34C	109.5
C12—C11—C1	115.5 (3)	H34A—C34—H34C	109.5
C12—C11—H11A	108.4	H34B—C34—H34C	109.5
C1—C11—H11A	108.4	C33—C35—H35A	109.5
C12—C11—H11B	108.4	C33—C35—H35B	109.5
C1—C11—H11B	108.4	C33—C35—H35C	109.5
H11A—C11—H11B	107.5	C33—C35'—H35D	109.5
C13—C12—C11	126.8 (3)	C33—C35'—H35E	109.5
C13—C12—H12A	116.6	H35D—C35'—H35E	109.5
C11—C12—H12A	116.6	C33—C35'—H35F	109.5
C12—C13—C15	120.6 (3)	H35D—C35'—H35F	109.5
C12—C13—C14	125.2 (3)	H35E—C35'—H35F	109.5
C15—C13—C14	114.2 (3)	C9—C41—H41A	109.5
C13—C14—H14A	109.5	C9—C41—H41B	109.5
C13—C14—H14B	109.5	H41A—C41—H41B	109.5
H14A—C14—H14B	109.5	C9—C41—H41C	109.5
C13—C14—H14C	109.5	H41A—C41—H41C	109.5
H14A—C14—H14C	109.5	H41B—C41—H41C	109.5
H14B—C14—H14C	109.5	C9—C42—H42A	109.5
C13—C15—H15A	109.5	C9—C42—H42B	109.5
C13—C15—H15B	109.5	H42A—C42—H42B	109.5
H15A—C15—H15B	109.5	C9—C42—H42C	109.5
C13—C15—H15C	109.5	H42A—C42—H42C	109.5
H15A—C15—H15C	109.5	H42B—C42—H42C	109.5
C6—C1—C2—O1	174.3 (3)	C31—C3—C7—C8	−77.5 (3)
C11—C1—C2—O1	49.6 (4)	C3—C7—C8—C9	−62.6 (4)
C21—C1—C2—O1	−67.4 (3)	C7—C8—C9—C10	45.2 (4)
C6—C1—C2—C3	−4.2 (4)	C7—C8—C9—C42	−75.7 (4)
C11—C1—C2—C3	−128.9 (3)	C7—C8—C9—C41	163.6 (3)
C21—C1—C2—C3	114.1 (3)	O3—C4—C10—C9	174.7 (3)
O1—C2—C3—C4	149.8 (3)	C3—C4—C10—C9	−1.0 (5)
C1—C2—C3—C4	−31.7 (4)	C42—C9—C10—C4	106.6 (4)
O1—C2—C3—C7	30.1 (4)	C41—C9—C10—C4	−133.3 (3)
C1—C2—C3—C7	−151.5 (3)	C8—C9—C10—C4	−14.8 (4)
O1—C2—C3—C31	−92.0 (3)	C2—C1—C11—C12	66.1 (3)
C1—C2—C3—C31	86.5 (3)	C6—C1—C11—C12	−60.6 (3)
C6—O3—C4—C10	153.2 (3)	C21—C1—C11—C12	−176.8 (3)
C6—O3—C4—C3	−30.6 (4)	C1—C11—C12—C13	−113.0 (4)
C2—C3—C4—C10	−134.2 (3)	C11—C12—C13—C15	−179.7 (3)
C7—C3—C4—C10	−13.0 (4)	C11—C12—C13—C14	0.3 (6)
C31—C3—C4—C10	109.2 (4)	C2—C1—C21—C22	−48.5 (4)
C2—C3—C4—O3	50.1 (3)	C6—C1—C21—C22	74.2 (3)
C7—C3—C4—O3	171.2 (2)	C11—C1—C21—C22	−167.4 (3)
C31—C3—C4—O3	−66.6 (3)	C1—C21—C22—C23	−104.8 (4)
C4—O3—C6—O2	173.1 (3)	C21—C22—C23—C25	−175.1 (3)
C4—O3—C6—C1	−10.8 (4)	C21—C22—C23—C24	5.7 (5)
C2—C1—C6—O2	−156.6 (3)	C4—C3—C31—C32	−177.0 (3)
C11—C1—C6—O2	−31.8 (4)	C2—C3—C31—C32	64.9 (3)
C21—C1—C6—O2	84.8 (4)	C7—C3—C31—C32	−56.6 (4)
C2—C1—C6—O3	27.5 (4)	C3—C31—C32—C33	155.0 (3)
C11—C1—C6—O3	152.3 (2)	C31—C32—C33—C35	11.5 (7)
C21—C1—C6—O3	−91.1 (3)	C31—C32—C33—C34	177.5 (3)
C4—C3—C7—C8	43.2 (3)	C31—C32—C33—C35'	−24.0 (9)
C2—C3—C7—C8	163.2 (2)