syn-Dispiro-[1,3-dioxolane-2,17'-penta-cyclo-[12.2.1.1.0.0]octa-decane-18',2''-[1,3]dioxolane]-7',15'-diene.

The title compound, C(22)H(28)O(4), is composed of a central octa-decane ring and two spiro-[bicyclo-[2.2.1]hept[2]ene-7,2'-[1,3]dioxolane] units. This polycycle has pseudo twofold symmetry and the central cyclo-octane ring has a distorted boat configuration.

Related literature

For related structures, see: Garcia et al. (1991 ▶); Tenbusch et al. (2010 ▶). For the chemistry of syn-bis­quinoxalines, see: Chou et al. (2005 ▶); Etzkorn et al. (2010 ▶).

Experimental

Crystal data

C22H28O4

M = 356.44

Monoclinic,

a = 11.4167 (11) Å

b = 6.7354 (7) Å

c = 24.185 (2) Å

β = 103.521 (9)°

V = 1808.2 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.71 mm−1

T = 295 K

0.35 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

8422 measured reflections

3248 independent reflections

2693 reflections with I > 2σ(I)

R int = 0.045

3 standard reflections every 79 reflections intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.05

3248 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae, et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041565/su2208sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041565/su2208Isup2.hkl

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

C22H28O4	F(000) = 768
Mr = 356.44	Dx = 1.309 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 11.4167 (11) Å	θ = 15.3–42.6°
b = 6.7354 (7) Å	µ = 0.71 mm−1
c = 24.185 (2) Å	T = 295 K
β = 103.521 (9)°	Prism, colorless
V = 1808.2 (3) Å3	0.35 × 0.20 × 0.20 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	θmax = 67.5°, θmin = 3.8°
Non–profiled ω/2θ scans	h = −13→0
8422 measured reflections	k = −8→8
3248 independent reflections	l = −28→28
2693 reflections with I > 2σ(I)	3 standard reflections every 79 reflections
Rint = 0.045	intensity decay: 2%

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0414P)2 + 0.4578P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.039	(Δ/σ)max < 0.001
wR(F2) = 0.106	Δρmax = 0.24 e Å−3
S = 1.05	Δρmin = −0.19 e Å−3
3248 reflections	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
236 parameters	Extinction coefficient: 0.0117 (6)
0 restraints

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

	x	y	z	Uiso*/Ueq
O1	0.49270 (9)	0.9050 (2)	−0.18532 (5)	0.0544 (4)
O2	0.56491 (10)	1.0106 (2)	−0.25975 (4)	0.0545 (4)
O3	0.58431 (10)	0.6331 (2)	0.05326 (5)	0.0597 (4)
O4	0.68575 (10)	0.66022 (19)	0.14523 (4)	0.0534 (4)
C1	0.68153 (12)	1.0631 (2)	−0.10437 (6)	0.0351 (4)
C2	0.72139 (12)	0.8459 (2)	−0.11521 (6)	0.0360 (4)
C3	0.84705 (13)	0.7735 (2)	−0.08405 (6)	0.0419 (5)
C4	0.87904 (12)	0.7689 (2)	−0.01860 (6)	0.0413 (5)
C5	0.77291 (12)	0.7502 (2)	0.00928 (6)	0.0348 (4)
C6	0.70386 (12)	0.9466 (2)	0.01680 (6)	0.0362 (4)
C7	0.75302 (14)	1.1468 (2)	0.00213 (6)	0.0423 (5)
C8	0.76760 (13)	1.1811 (2)	−0.05857 (6)	0.0399 (5)
C9	0.65659 (13)	1.1569 (2)	−0.16468 (6)	0.0416 (5)
C10	0.80267 (14)	0.9816 (3)	−0.19355 (7)	0.0535 (6)
C11	0.77312 (14)	1.1653 (3)	−0.18360 (6)	0.0509 (6)
C12	0.70828 (13)	0.8439 (3)	−0.18100 (6)	0.0445 (5)
C13	0.59793 (13)	0.9774 (3)	−0.20041 (6)	0.0430 (5)
C14	0.80596 (13)	0.6639 (2)	0.07062 (6)	0.0408 (5)
C15	0.89060 (14)	0.8058 (3)	0.10824 (6)	0.0484 (5)
C16	0.82908 (15)	0.9654 (3)	0.11512 (6)	0.0500 (5)
C17	0.70117 (14)	0.9382 (2)	0.08140 (6)	0.0428 (5)
C18	0.68912 (13)	0.7153 (2)	0.08916 (6)	0.0419 (5)
C19	0.39160 (16)	0.9459 (4)	−0.23040 (8)	0.0676 (7)
C20	0.44134 (16)	1.0615 (3)	−0.27232 (8)	0.0645 (7)
C21	0.53301 (14)	0.4946 (3)	0.08401 (7)	0.0488 (5)
C22	0.62046 (16)	0.4807 (3)	0.14092 (8)	0.0564 (6)
H1	0.60440	1.05420	−0.09330	0.0420*
H2	0.66180	0.75390	−0.10640	0.0430*
H3A	0.90590	0.85690	−0.09600	0.0500*
H3B	0.85730	0.64010	−0.09730	0.0500*
H4A	0.93320	0.65830	−0.00620	0.0500*
H4B	0.92250	0.88970	−0.00490	0.0500*
H5	0.71460	0.65960	−0.01410	0.0420*
H6	0.62090	0.93370	−0.00570	0.0430*
H7C	0.70030	1.24980	0.01050	0.0510*
H7D	0.83120	1.16620	0.02780	0.0510*
H8C	0.75610	1.32130	−0.06740	0.0480*
H8D	0.84950	1.14760	−0.05990	0.0480*
H9	0.60900	1.27950	−0.16970	0.0500*
H10	0.87030	0.94370	−0.20620	0.0640*
H11	0.81640	1.27930	−0.18760	0.0610*
H12	0.70340	0.71250	−0.19880	0.0530*
H14	0.82980	0.52380	0.07380	0.0490*
H15	0.97210	0.78450	0.12390	0.0580*
H16	0.85920	1.07580	0.13700	0.0600*
H17	0.64040	1.02140	0.09280	0.0510*
H19G	0.33210	1.02310	−0.21700	0.0810*
H19H	0.35450	0.82380	−0.24720	0.0810*
H20E	0.40210	1.02430	−0.31100	0.0770*
H20F	0.43090	1.20290	−0.26760	0.0770*
H21A	0.52350	0.36670	0.06510	0.0590*
H21B	0.45480	0.53980	0.08820	0.0590*
H22C	0.57840	0.46940	0.17130	0.0680*
H22D	0.67340	0.36730	0.14240	0.0680*

	U11	U22	U33	U12	U13	U23
O1	0.0405 (6)	0.0779 (9)	0.0398 (6)	−0.0133 (5)	−0.0009 (4)	0.0090 (6)
O2	0.0556 (6)	0.0750 (9)	0.0288 (5)	0.0006 (6)	0.0017 (5)	0.0037 (5)
O3	0.0506 (6)	0.0824 (9)	0.0389 (6)	−0.0342 (6)	−0.0039 (5)	0.0101 (6)
O4	0.0637 (7)	0.0621 (8)	0.0314 (6)	−0.0194 (6)	0.0048 (5)	0.0056 (5)
C1	0.0343 (7)	0.0386 (8)	0.0312 (7)	−0.0020 (6)	0.0055 (5)	0.0016 (6)
C2	0.0367 (7)	0.0384 (8)	0.0319 (7)	−0.0039 (6)	0.0061 (5)	0.0006 (6)
C3	0.0398 (7)	0.0443 (9)	0.0424 (8)	0.0042 (6)	0.0113 (6)	0.0030 (7)
C4	0.0342 (7)	0.0452 (9)	0.0412 (8)	0.0014 (6)	0.0021 (6)	0.0035 (7)
C5	0.0355 (7)	0.0340 (8)	0.0311 (7)	−0.0065 (6)	0.0000 (5)	−0.0010 (6)
C6	0.0367 (7)	0.0375 (8)	0.0315 (7)	−0.0043 (6)	0.0021 (5)	−0.0010 (6)
C7	0.0535 (8)	0.0346 (8)	0.0363 (8)	−0.0053 (6)	0.0055 (6)	−0.0029 (6)
C8	0.0460 (8)	0.0331 (8)	0.0382 (8)	−0.0057 (6)	0.0051 (6)	0.0018 (6)
C9	0.0464 (8)	0.0421 (9)	0.0339 (8)	0.0000 (6)	0.0046 (6)	0.0049 (7)
C10	0.0456 (8)	0.0806 (13)	0.0365 (8)	0.0042 (8)	0.0143 (7)	0.0091 (9)
C11	0.0487 (9)	0.0662 (12)	0.0355 (8)	−0.0129 (8)	0.0052 (7)	0.0122 (8)
C12	0.0518 (9)	0.0470 (10)	0.0338 (8)	0.0015 (7)	0.0084 (6)	−0.0043 (7)
C13	0.0442 (8)	0.0543 (10)	0.0283 (7)	−0.0047 (7)	0.0041 (6)	0.0033 (7)
C14	0.0444 (8)	0.0380 (8)	0.0346 (8)	−0.0049 (6)	−0.0017 (6)	0.0030 (6)
C15	0.0410 (8)	0.0607 (11)	0.0358 (8)	−0.0132 (7)	−0.0063 (6)	0.0049 (8)
C16	0.0623 (10)	0.0507 (10)	0.0313 (8)	−0.0204 (8)	−0.0006 (7)	−0.0055 (7)
C17	0.0493 (8)	0.0454 (9)	0.0328 (8)	−0.0034 (7)	0.0079 (6)	−0.0024 (7)
C18	0.0427 (8)	0.0517 (9)	0.0265 (7)	−0.0136 (7)	−0.0017 (6)	0.0020 (7)
C19	0.0475 (9)	0.0934 (16)	0.0524 (11)	−0.0054 (10)	−0.0072 (8)	0.0120 (10)
C20	0.0559 (10)	0.0827 (15)	0.0455 (10)	0.0009 (9)	−0.0074 (8)	0.0076 (10)
C21	0.0448 (8)	0.0518 (10)	0.0501 (9)	−0.0117 (7)	0.0118 (7)	0.0008 (8)
C22	0.0569 (10)	0.0599 (11)	0.0510 (10)	−0.0133 (8)	0.0099 (8)	0.0112 (9)

O1—C13	1.4210 (19)	C19—C20	1.492 (3)
O1—C19	1.417 (2)	C21—C22	1.503 (3)
O2—C13	1.4138 (17)	C1—H1	0.9800
O2—C20	1.414 (2)	C2—H2	0.9800
O3—C18	1.4165 (19)	C3—H3A	0.9700
O3—C21	1.404 (2)	C3—H3B	0.9700
O4—C18	1.4151 (17)	C4—H4A	0.9700
O4—C22	1.411 (2)	C4—H4B	0.9700
C1—C2	1.5722 (19)	C5—H5	0.9800
C1—C8	1.522 (2)	C6—H6	0.9800
C1—C9	1.554 (2)	C7—H7C	0.9700
C2—C3	1.536 (2)	C7—H7D	0.9700
C2—C12	1.563 (2)	C8—H8C	0.9700
C3—C4	1.539 (2)	C8—H8D	0.9700
C4—C5	1.523 (2)	C9—H9	0.9800
C5—C6	1.5721 (19)	C10—H10	0.9300
C5—C14	1.555 (2)	C11—H11	0.9300
C6—C7	1.534 (2)	C12—H12	0.9800
C6—C17	1.571 (2)	C14—H14	0.9800
C7—C8	1.533 (2)	C15—H15	0.9300
C9—C11	1.506 (2)	C16—H16	0.9300
C9—C13	1.545 (2)	C17—H17	0.9800
C10—C11	1.319 (3)	C19—H19G	0.9700
C10—C12	1.506 (2)	C19—H19H	0.9700
C12—C13	1.530 (2)	C20—H20E	0.9700
C14—C15	1.505 (2)	C20—H20F	0.9700
C14—C18	1.543 (2)	C21—H21A	0.9700
C15—C16	1.316 (3)	C21—H21B	0.9700
C16—C17	1.508 (2)	C22—H22C	0.9700
C17—C18	1.5232 (19)	C22—H22D	0.9700
C13—O1—C19	108.73 (13)	H3A—C3—H3B	107.00
C13—O2—C20	105.81 (12)	C3—C4—H4A	108.00
C18—O3—C21	109.41 (12)	C3—C4—H4B	108.00
C18—O4—C22	106.62 (12)	C5—C4—H4A	108.00
C2—C1—C8	116.40 (12)	C5—C4—H4B	108.00
C2—C1—C9	102.62 (11)	H4A—C4—H4B	107.00
C8—C1—C9	114.61 (11)	C4—C5—H5	107.00
C1—C2—C3	119.16 (11)	C6—C5—H5	107.00
C1—C2—C12	102.43 (12)	C14—C5—H5	107.00
C3—C2—C12	110.67 (12)	C5—C6—H6	108.00
C2—C3—C4	118.74 (12)	C7—C6—H6	108.00
C3—C4—C5	115.77 (12)	C17—C6—H6	108.00
C4—C5—C6	116.99 (11)	C6—C7—H7C	108.00
C4—C5—C14	114.35 (12)	C6—C7—H7D	108.00
C6—C5—C14	102.74 (11)	C8—C7—H7C	108.00
C5—C6—C7	119.51 (12)	C8—C7—H7D	108.00
C5—C6—C17	102.22 (11)	H7C—C7—H7D	107.00
C7—C6—C17	110.80 (11)	C1—C8—H8C	108.00
C6—C7—C8	118.79 (12)	C1—C8—H8D	109.00
C1—C8—C7	114.97 (12)	C7—C8—H8C	109.00
C1—C9—C11	108.64 (12)	C7—C8—H8D	109.00
C1—C9—C13	99.63 (11)	H8C—C8—H8D	108.00
C11—C9—C13	99.07 (12)	C1—C9—H9	116.00
C11—C10—C12	108.38 (15)	C11—C9—H9	116.00
C9—C11—C10	107.58 (15)	C13—C9—H9	116.00
C2—C12—C10	107.29 (13)	C11—C10—H10	126.00
C2—C12—C13	100.56 (12)	C12—C10—H10	126.00
C10—C12—C13	98.80 (15)	C9—C11—H11	126.00
O1—C13—O2	105.91 (12)	C10—C11—H11	126.00
O1—C13—C9	114.01 (13)	C2—C12—H12	116.00
O1—C13—C12	113.87 (15)	C10—C12—H12	116.00
O2—C13—C9	114.95 (15)	C13—C12—H12	116.00
O2—C13—C12	114.18 (13)	C5—C14—H14	116.00
C9—C13—C12	94.02 (12)	C15—C14—H14	116.00
C5—C14—C15	108.52 (12)	C18—C14—H14	116.00
C5—C14—C18	99.20 (11)	C14—C15—H15	126.00
C15—C14—C18	99.11 (11)	C16—C15—H15	126.00
C14—C15—C16	108.01 (14)	C15—C16—H16	126.00
C15—C16—C17	108.08 (15)	C17—C16—H16	126.00
C6—C17—C16	106.97 (12)	C6—C17—H17	116.00
C6—C17—C18	100.45 (11)	C16—C17—H17	116.00
C16—C17—C18	99.04 (13)	C18—C17—H17	116.00
O3—C18—O4	106.06 (12)	O1—C19—H19G	111.00
O3—C18—C14	113.46 (12)	O1—C19—H19H	111.00
O3—C18—C17	113.42 (12)	C20—C19—H19G	111.00
O4—C18—C14	116.03 (12)	C20—C19—H19H	111.00
O4—C18—C17	113.58 (12)	H19G—C19—H19H	109.00
C14—C18—C17	94.37 (11)	O2—C20—H20E	111.00
O1—C19—C20	104.67 (15)	O2—C20—H20F	111.00
O2—C20—C19	104.27 (15)	C19—C20—H20E	111.00
O3—C21—C22	104.87 (14)	C19—C20—H20F	111.00
O4—C22—C21	103.92 (15)	H20E—C20—H20F	109.00
C2—C1—H1	108.00	O3—C21—H21A	111.00
C8—C1—H1	108.00	O3—C21—H21B	111.00
C9—C1—H1	108.00	C22—C21—H21A	111.00
C1—C2—H2	108.00	C22—C21—H21B	111.00
C3—C2—H2	108.00	H21A—C21—H21B	109.00
C12—C2—H2	108.00	O4—C22—H22C	111.00
C2—C3—H3A	108.00	O4—C22—H22D	111.00
C2—C3—H3B	108.00	C21—C22—H22C	111.00
C4—C3—H3A	108.00	C21—C22—H22D	111.00
C4—C3—H3B	108.00	H22C—C22—H22D	109.00
C19—O1—C13—O2	−16.0 (2)	C5—C6—C7—C8	59.18 (18)
C19—O1—C13—C9	111.44 (16)	C17—C6—C7—C8	177.55 (13)
C19—O1—C13—C12	−142.24 (16)	C5—C6—C17—C16	68.32 (14)
C13—O1—C19—C20	−4.0 (2)	C5—C6—C17—C18	−34.58 (14)
C20—O2—C13—O1	30.52 (18)	C7—C6—C17—C16	−60.10 (16)
C20—O2—C13—C9	−96.31 (16)	C7—C6—C17—C18	−162.99 (12)
C20—O2—C13—C12	156.61 (15)	C6—C7—C8—C1	27.76 (19)
C13—O2—C20—C19	−32.55 (19)	C1—C9—C11—C10	70.25 (15)
C21—O3—C18—O4	−13.28 (16)	C13—C9—C11—C10	−33.20 (15)
C21—O3—C18—C14	115.23 (14)	C1—C9—C13—O1	58.67 (16)
C21—O3—C18—C17	−138.60 (14)	C1—C9—C13—O2	−178.77 (12)
C18—O3—C21—C22	−5.34 (18)	C1—C9—C13—C12	−59.72 (12)
C22—O4—C18—O3	27.73 (16)	C11—C9—C13—O1	169.48 (13)
C22—O4—C18—C14	−99.25 (15)	C11—C9—C13—O2	−67.95 (15)
C22—O4—C18—C17	152.96 (14)	C11—C9—C13—C12	51.10 (13)
C18—O4—C22—C21	−30.43 (17)	C12—C10—C11—C9	−0.71 (17)
C8—C1—C2—C3	−5.80 (18)	C11—C10—C12—C2	−69.33 (17)
C8—C1—C2—C12	−128.27 (13)	C11—C10—C12—C13	34.70 (16)
C9—C1—C2—C3	120.19 (13)	C2—C12—C13—O1	−60.17 (16)
C9—C1—C2—C12	−2.28 (14)	C2—C12—C13—O2	178.01 (14)
C2—C1—C8—C7	−85.21 (15)	C2—C12—C13—C9	58.33 (13)
C9—C1—C8—C7	155.07 (12)	C10—C12—C13—O1	−169.73 (13)
C2—C1—C9—C11	−64.62 (14)	C10—C12—C13—O2	68.45 (17)
C2—C1—C9—C13	38.44 (13)	C10—C12—C13—C9	−51.23 (13)
C8—C1—C9—C11	62.51 (16)	C5—C14—C15—C16	70.53 (16)
C8—C1—C9—C13	165.58 (12)	C18—C14—C15—C16	−32.44 (15)
C1—C2—C3—C4	60.36 (17)	C5—C14—C18—O3	57.69 (14)
C12—C2—C3—C4	178.65 (13)	C5—C14—C18—O4	−179.12 (11)
C1—C2—C12—C10	67.63 (15)	C5—C14—C18—C17	−60.19 (12)
C1—C2—C12—C13	−35.14 (15)	C15—C14—C18—O3	168.29 (12)
C3—C2—C12—C10	−60.42 (17)	C15—C14—C18—O4	−68.52 (15)
C3—C2—C12—C13	−163.20 (12)	C15—C14—C18—C17	50.41 (12)
C2—C3—C4—C5	25.27 (17)	C14—C15—C16—C17	−1.07 (17)
C3—C4—C5—C6	−82.83 (15)	C15—C16—C17—C6	−69.25 (16)
C3—C4—C5—C14	157.02 (11)	C15—C16—C17—C18	34.67 (16)
C4—C5—C6—C7	−6.45 (18)	C6—C17—C18—O3	−59.54 (15)
C4—C5—C6—C17	−129.14 (13)	C6—C17—C18—O4	179.28 (12)
C14—C5—C6—C7	119.68 (13)	C6—C17—C18—C14	58.38 (12)
C14—C5—C6—C17	−3.01 (13)	C16—C17—C18—O3	−168.80 (12)
C4—C5—C14—C15	63.85 (15)	C16—C17—C18—O4	70.02 (15)
C4—C5—C14—C18	166.77 (11)	C16—C17—C18—C14	−50.88 (12)
C6—C5—C14—C15	−63.96 (14)	O1—C19—C20—O2	22.4 (2)
C6—C5—C14—C18	38.95 (12)	O3—C21—C22—O4	21.88 (18)