anti-1',6',7',8',9',14',15',16'-Octa-chloro-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(20)Cl(8)O(4), was prepared as part of the synthesis of precursors for the preparation of fluorinated mol-ecular tweezers. The mol-ecule sits on an inversion center, thus requiring that the cyclo-octane ring adopt a chair conformation.

Related literature

For related structures, see: Garcia et al. (1991b ▶,c ▶). For related chemistry on analogous polycyclic scaffolds, see: Garcia et al. (1991a ▶); Chou et al. (2005 ▶)

Experimental

Crystal data

C22H20Cl8O4

M = 631.98

Monoclinic,

a = 9.5332 (7) Å

b = 7.9121 (6) Å

c = 17.014 (2) Å

β = 101.099 (8)°

V = 1259.3 (2) Å3

Z = 2

Cu Kα radiation

μ = 8.44 mm−1

T = 295 K

0.25 × 0.20 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.190, T max = 0.561

4703 measured reflections

2275 independent reflections

1702 reflections with I > 2σ(I)

R int = 0.047

3 standard reflections every 62 reflections intensity decay: 13%

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.118

S = 1.05

2275 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.47 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: DIRDIF08 (Beurskens et al., 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024669/jh2171sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024669/jh2171Isup2.hkl

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

C22H20Cl8O4	F(000) = 640
Mr = 631.98	Dx = 1.677 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.5332 (7) Å	θ = 5.3–18.2°
b = 7.9121 (6) Å	µ = 8.44 mm−1
c = 17.014 (2) Å	T = 295 K
β = 101.099 (8)°	Prism, colorless
V = 1259.3 (2) Å3	0.25 × 0.20 × 0.08 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	Rint = 0.047
graphite	θmax = 67.4°, θmin = 4.7°
non–profiled ω/2θ scans	h = −11→11
Absorption correction: multi-scan (Blessing, 1995)	k = −9→9
Tmin = 0.190, Tmax = 0.561	l = −20→0
4703 measured reflections	3 standard reflections every 62 reflections
2275 independent reflections	intensity decay: 13%
1702 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.5139P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2275 reflections	Δρmax = 0.36 e Å−3
155 parameters	Δρmin = −0.47 e Å−3
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0010 (3)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	0.56200 (8)	0.74022 (12)	1.00965 (5)	0.0547 (3)
Cl4	0.77203 (10)	0.88651 (12)	0.73738 (5)	0.0557 (3)
Cl2	0.79698 (10)	0.44785 (12)	0.98707 (7)	0.0657 (3)
Cl3	0.93205 (10)	0.54119 (14)	0.82005 (6)	0.0648 (3)
O1	0.5602 (2)	0.9949 (3)	0.85728 (14)	0.0479 (5)
O2	0.5274 (2)	0.7211 (3)	0.81904 (14)	0.0494 (6)
C5	0.7945 (3)	0.9248 (4)	0.97774 (18)	0.0380 (6)
H5	0.7385	1.0223	0.9895	0.046*
C10	0.9019 (3)	0.8836 (4)	1.05363 (19)	0.0410 (7)
H10A	0.9704	0.8028	1.0405	0.049*
H10B	0.8517	0.8296	1.0914	0.049*
C11	0.9836 (3)	1.0369 (4)	1.09459 (19)	0.0434 (7)
H11A	0.9466	1.1379	1.0655	0.052*
H11B	0.9643	1.0463	1.1483	0.052*
C7	0.7734 (3)	0.8387 (4)	0.83817 (19)	0.0424 (7)
C1	0.4108 (3)	0.9714 (5)	0.8255 (2)	0.0544 (9)
H1A	0.3719	1.0666	0.7925	0.065*
H1B	0.3574	0.9574	0.8682	0.065*
C8	0.8224 (3)	0.6619 (4)	0.8649 (2)	0.0439 (7)
C6	0.8545 (3)	0.9680 (4)	0.89984 (17)	0.0381 (6)
H6	0.8212	1.0815	0.8822	0.046*
C3	0.6241 (3)	0.8363 (4)	0.86189 (19)	0.0404 (7)
C4	0.6875 (3)	0.7784 (4)	0.94892 (18)	0.0392 (7)
C9	0.7714 (3)	0.6257 (4)	0.9301 (2)	0.0432 (7)
C2	0.4067 (4)	0.8167 (6)	0.7776 (3)	0.0729 (12)
H2A	0.318	0.7555	0.7762	0.088*
H2B	0.4167	0.8422	0.7232	0.088*

	U11	U22	U33	U12	U13	U23
Cl1	0.0427 (4)	0.0648 (5)	0.0619 (5)	−0.0091 (4)	0.0232 (4)	−0.0018 (4)
Cl4	0.0560 (5)	0.0698 (6)	0.0420 (4)	−0.0103 (4)	0.0113 (3)	−0.0032 (4)
Cl2	0.0621 (6)	0.0497 (5)	0.0861 (7)	0.0058 (4)	0.0161 (5)	0.0163 (4)
Cl3	0.0525 (5)	0.0752 (6)	0.0686 (6)	0.0162 (4)	0.0161 (4)	−0.0218 (5)
O1	0.0365 (11)	0.0445 (12)	0.0602 (14)	0.0041 (9)	0.0033 (10)	−0.0058 (10)
O2	0.0357 (11)	0.0508 (13)	0.0591 (14)	−0.0048 (9)	0.0021 (10)	−0.0114 (11)
C5	0.0330 (14)	0.0402 (15)	0.0423 (16)	−0.0014 (12)	0.0113 (12)	−0.0037 (12)
C10	0.0362 (15)	0.0455 (16)	0.0430 (16)	−0.0041 (13)	0.0119 (13)	0.0019 (13)
C11	0.0381 (16)	0.0537 (18)	0.0406 (17)	−0.0047 (13)	0.0127 (13)	−0.0034 (14)
C7	0.0374 (15)	0.0500 (18)	0.0412 (16)	−0.0025 (14)	0.0108 (13)	−0.0043 (13)
C1	0.0339 (16)	0.062 (2)	0.065 (2)	0.0057 (15)	0.0040 (15)	0.0036 (17)
C8	0.0331 (14)	0.0465 (17)	0.0527 (18)	0.0015 (13)	0.0097 (13)	−0.0124 (14)
C6	0.0356 (15)	0.0406 (15)	0.0388 (16)	−0.0018 (12)	0.0086 (12)	−0.0017 (12)
C3	0.0331 (15)	0.0401 (15)	0.0474 (17)	−0.0008 (12)	0.0061 (13)	−0.0062 (13)
C4	0.0329 (14)	0.0427 (16)	0.0442 (16)	−0.0007 (12)	0.0126 (12)	−0.0020 (13)
C9	0.0361 (15)	0.0390 (15)	0.0538 (19)	0.0000 (13)	0.0071 (14)	−0.0007 (14)
C2	0.046 (2)	0.077 (3)	0.085 (3)	0.008 (2)	−0.014 (2)	−0.015 (2)

Cl1—C4	1.751 (3)	C11—H11A	0.97
Cl4—C7	1.754 (3)	C11—H11B	0.97
Cl2—C9	1.700 (3)	C7—C8	1.516 (4)
Cl3—C8	1.701 (3)	C7—C3	1.553 (4)
O1—C3	1.391 (4)	C7—C6	1.560 (4)
O1—C1	1.435 (4)	C1—C2	1.467 (6)
O2—C3	1.397 (4)	C1—H1A	0.97
O2—C2	1.443 (4)	C1—H1B	0.97
C5—C10	1.521 (4)	C8—C9	1.326 (5)
C5—C4	1.559 (4)	C6—C11i	1.528 (4)
C5—C6	1.579 (4)	C6—H6	0.98
C5—H5	0.98	C3—C4	1.557 (4)
C10—C11	1.535 (4)	C4—C9	1.517 (4)
C10—H10A	0.97	C2—H2A	0.97
C10—H10B	0.97	C2—H2B	0.97
C11—C6i	1.528 (4)
C3—O1—C1	107.2 (2)	H1A—C1—H1B	109
C3—O2—C2	107.3 (3)	C9—C8—C7	108.0 (3)
C10—C5—C4	113.6 (3)	C9—C8—Cl3	127.6 (3)
C10—C5—C6	117.7 (2)	C7—C8—Cl3	124.3 (2)
C4—C5—C6	102.6 (2)	C11i—C6—C7	112.9 (2)
C10—C5—H5	107.5	C11i—C6—C5	117.9 (2)
C4—C5—H5	107.5	C7—C6—C5	102.1 (2)
C6—C5—H5	107.5	C11i—C6—H6	107.8
C5—C10—C11	114.6 (3)	C7—C6—H6	107.8
C5—C10—H10A	108.6	C5—C6—H6	107.8
C11—C10—H10A	108.6	O1—C3—O2	108.7 (2)
C5—C10—H10B	108.6	O1—C3—C7	112.8 (3)
C11—C10—H10B	108.6	O2—C3—C7	114.7 (3)
H10A—C10—H10B	107.6	O1—C3—C4	113.9 (2)
C6i—C11—C10	115.3 (3)	O2—C3—C4	113.6 (3)
C6i—C11—H11A	108.5	C7—C3—C4	92.5 (2)
C10—C11—H11A	108.5	C9—C4—C3	99.0 (2)
C6i—C11—H11B	108.5	C9—C4—C5	108.6 (2)
C10—C11—H11B	108.5	C3—C4—C5	101.0 (2)
H11A—C11—H11B	107.5	C9—C4—Cl1	115.8 (2)
C8—C7—C3	99.0 (2)	C3—C4—Cl1	115.3 (2)
C8—C7—C6	108.6 (3)	C5—C4—Cl1	115.0 (2)
C3—C7—C6	101.2 (2)	C8—C9—C4	107.3 (3)
C8—C7—Cl4	115.9 (2)	C8—C9—Cl2	128.4 (3)
C3—C7—Cl4	115.0 (2)	C4—C9—Cl2	124.2 (2)
C6—C7—Cl4	115.2 (2)	O2—C2—C1	103.4 (3)
O1—C1—C2	103.6 (3)	O2—C2—H2A	111.1
O1—C1—H1A	111	C1—C2—H2A	111.1
C2—C1—H1A	111	O2—C2—H2B	111.1
O1—C1—H1B	111	C1—C2—H2B	111.1
C2—C1—H1B	111	H2A—C2—H2B	109