7-Iodo-3,3-diphenyl-octa-hydro-benzo-furan.

The title compound, C20H21IO, was synthesized by cyclo-haloetherification of 2-(cyclo-hex-2-en-yl)-2,2-diphenyl-ethanol in CH2Cl2, and crystallized with two independent mol-ecules in the asymmetric unit. The six-membered cyclo-hexane ring adopts a chair conformation, while the five-membered ring adopts an envelope conformation with the fused C atom opposite the O atom as the flap in each case [displacements of the flap atoms = 0.6813 (3) and 0.6679 (3) Å]. In the crystal, mol-ecules are linked via pairs of C-H⋯π inter-actions, forming inversion dimers.

Related literature

For the title compound as a core structure of many drugs and natural products, see: Huang & Chen (2007 ▶); Trost et al. (2003 ▶). For the synthesis of 2-(cyclo­hex-2-en­yl)-2,2-diphenyl­ethanol, see: Brooner & Widenhoefer (2011 ▶).

Experimental

Crystal data

C20H21IO

M = 404.27

Triclinic,

a = 11.4082 (18) Å

b = 12.523 (2) Å

c = 14.007 (3) Å

α = 73.306 (8)°

β = 71.646 (8)°

γ = 64.945 (7)°

V = 1692.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.89 mm−1

T = 153 K

0.33 × 0.27 × 0.10 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.572, T max = 0.833

19455 measured reflections

9610 independent reflections

7599 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.091

S = 1.00

9610 reflections

397 parameters

H-atom parameters constrained

Δρmax = 1.05 e Å−3

Δρmin = −0.75 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007563/hg5298sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007563/hg5298Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007563/hg5298Isup3.cml

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

C20H21IO	Z = 4
Mr = 404.27	F(000) = 808
Triclinic, P1	Dx = 1.586 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.4082 (18) Å	Cell parameters from 5864 reflections
b = 12.523 (2) Å	θ = 2.2–30.0°
c = 14.007 (3) Å	µ = 1.89 mm−1
α = 73.306 (8)°	T = 153 K
β = 71.646 (8)°	Block, colourless
γ = 64.945 (7)°	0.33 × 0.27 × 0.10 mm
V = 1692.8 (5) Å3

Rigaku AFC10/Saturn724+ diffractometer	9610 independent reflections
Radiation source: Rotating Anode	7599 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 28.5714 pixels mm-1	θmax = 30.0°, θmin = 2.2°
phi and ω scans	h = −16→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −17→16
Tmin = 0.572, Tmax = 0.833	l = −19→19
19455 measured 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0318P)2 + 1.060P] where P = (Fo2 + 2Fc2)/3
9610 reflections	(Δ/σ)max = 0.002
397 parameters	Δρmax = 1.05 e Å−3
0 restraints	Δρmin = −0.75 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
I1	0.65947 (2)	0.703016 (18)	0.295052 (16)	0.03449 (6)
O1	0.53230 (19)	0.40425 (16)	0.40367 (15)	0.0228 (4)
C1	0.5264 (2)	0.5248 (2)	0.3578 (2)	0.0184 (5)
H1	0.4776	0.5777	0.4103	0.022*
C2	0.6681 (3)	0.5206 (2)	0.3193 (2)	0.0216 (5)
H2	0.7177	0.4710	0.3743	0.026*
C3	0.7423 (3)	0.4681 (3)	0.2228 (2)	0.0278 (6)
H3A	0.7611	0.3809	0.2388	0.033*
H3B	0.8283	0.4796	0.1973	0.033*
C4	0.6631 (3)	0.5265 (3)	0.1397 (2)	0.0285 (6)
H4A	0.7133	0.4889	0.0784	0.034*
H4B	0.6493	0.6127	0.1201	0.034*
C5	0.5288 (3)	0.5116 (3)	0.1782 (2)	0.0228 (5)
H5A	0.5438	0.4253	0.1913	0.027*
H5B	0.4778	0.5523	0.1240	0.027*
C6	0.4460 (2)	0.5624 (2)	0.27622 (19)	0.0176 (5)
H6	0.4037	0.6517	0.2601	0.021*
C7	0.3390 (2)	0.5062 (2)	0.33450 (19)	0.0176 (5)
C8	0.4302 (3)	0.3834 (2)	0.3831 (2)	0.0212 (5)
H8A	0.3792	0.3500	0.4472	0.025*
H8B	0.4686	0.3260	0.3355	0.025*
C9	0.2348 (2)	0.5739 (2)	0.4198 (2)	0.0196 (5)
C10	0.1516 (3)	0.5193 (3)	0.4926 (2)	0.0241 (6)
H10	0.1619	0.4411	0.4891	0.029*
C11	0.0547 (3)	0.5757 (3)	0.5698 (2)	0.0304 (7)
H11	0.0001	0.5360	0.6187	0.036*
C12	0.0376 (3)	0.6890 (3)	0.5754 (2)	0.0314 (7)
H12	−0.0294	0.7283	0.6279	0.038*
C13	0.1182 (3)	0.7460 (3)	0.5043 (2)	0.0302 (7)
H13	0.1067	0.8244	0.5082	0.036*
C14	0.2156 (3)	0.6888 (3)	0.4276 (2)	0.0241 (6)
H14	0.2704	0.7288	0.3794	0.029*
C15	0.2651 (2)	0.4991 (2)	0.2641 (2)	0.0195 (5)
C16	0.2684 (3)	0.3913 (3)	0.2510 (2)	0.0250 (6)
H16	0.3194	0.3175	0.2864	0.030*
C17	0.1972 (3)	0.3913 (3)	0.1862 (2)	0.0300 (7)
H17	0.2004	0.3174	0.1777	0.036*
C18	0.1223 (3)	0.4975 (3)	0.1342 (2)	0.0296 (6)
H18	0.0736	0.4969	0.0905	0.036*
C19	0.1185 (3)	0.6049 (3)	0.1461 (2)	0.0311 (7)
H19	0.0671	0.6783	0.1104	0.037*
C20	0.1893 (3)	0.6057 (3)	0.2100 (2)	0.0260 (6)
H20	0.1863	0.6800	0.2172	0.031*
I1'	1.19069 (2)	1.181469 (19)	0.013330 (16)	0.03506 (7)
O1'	1.02918 (19)	0.90326 (17)	0.12779 (15)	0.0251 (4)
C1'	1.0347 (3)	1.0201 (2)	0.1134 (2)	0.0203 (5)
H1'	0.9883	1.0756	0.0581	0.024*
C2'	1.1807 (3)	1.0044 (3)	0.0810 (2)	0.0245 (6)
H2'	1.2252	0.9533	0.0270	0.029*
C3'	1.2537 (3)	0.9465 (3)	0.1671 (2)	0.0305 (7)
H3'1	1.3435	0.9502	0.1426	0.037*
H3'2	1.2639	0.8610	0.1875	0.037*
C4'	1.1806 (3)	1.0078 (3)	0.2598 (2)	0.0301 (6)
H4'1	1.1757	1.0918	0.2411	0.036*
H4'2	1.2300	0.9663	0.3150	0.036*
C5'	1.0407 (3)	1.0052 (3)	0.2979 (2)	0.0256 (6)
H5'1	0.9939	1.0483	0.3563	0.031*
H5'2	1.0471	0.9210	0.3230	0.031*
C6'	0.9582 (3)	1.0620 (2)	0.21581 (19)	0.0187 (5)
H6'	0.9238	1.1514	0.2063	0.022*
C7'	0.8417 (3)	1.0166 (2)	0.2427 (2)	0.0187 (5)
C8'	0.9195 (3)	0.8919 (2)	0.2105 (2)	0.0229 (6)
H8'1	0.9521	0.8306	0.2686	0.027*
H8'2	0.8617	0.8680	0.1878	0.027*
C9'	0.7693 (3)	1.0112 (2)	0.3550 (2)	0.0195 (5)
C10'	0.7127 (3)	1.1150 (2)	0.3963 (2)	0.0238 (6)
H10'	0.7222	1.1868	0.3546	0.029*
C11'	0.6425 (3)	1.1161 (3)	0.4972 (2)	0.0273 (6)
H11'	0.6047	1.1879	0.5242	0.033*
C12'	0.6277 (3)	1.0117 (3)	0.5583 (2)	0.0322 (7)
H12'	0.5803	1.0116	0.6276	0.039*
C13'	0.6820 (3)	0.9087 (3)	0.5183 (2)	0.0368 (7)
H13'	0.6707	0.8376	0.5600	0.044*
C14'	0.7535 (3)	0.9072 (3)	0.4174 (2)	0.0295 (6)
H14'	0.7916	0.8349	0.3911	0.035*
C15'	0.7364 (3)	1.0920 (2)	0.1781 (2)	0.0198 (5)
C16'	0.6360 (3)	1.0507 (3)	0.1877 (2)	0.0271 (6)
H16'	0.6351	0.9781	0.2331	0.032*
C17'	0.5377 (3)	1.1134 (3)	0.1324 (2)	0.0333 (7)
H17'	0.4708	1.0836	0.1398	0.040*
C18'	0.5376 (3)	1.2199 (3)	0.0662 (2)	0.0332 (7)
H18'	0.4704	1.2634	0.0283	0.040*
C19'	0.6352 (3)	1.2623 (3)	0.0557 (2)	0.0288 (6)
H19'	0.6356	1.3348	0.0100	0.035*
C20'	0.7336 (3)	1.1995 (2)	0.1118 (2)	0.0232 (6)
H20'	0.7995	1.2304	0.1047	0.028*

	U11	U22	U33	U12	U13	U23
I1	0.04589 (13)	0.03359 (11)	0.03171 (11)	−0.02655 (10)	−0.00455 (9)	−0.00285 (9)
O1	0.0265 (10)	0.0197 (9)	0.0248 (10)	−0.0122 (8)	−0.0108 (8)	0.0038 (8)
C1	0.0200 (12)	0.0202 (12)	0.0166 (12)	−0.0102 (10)	−0.0033 (9)	−0.0018 (10)
C2	0.0205 (12)	0.0250 (13)	0.0213 (13)	−0.0099 (11)	−0.0060 (10)	−0.0033 (11)
C3	0.0201 (13)	0.0360 (16)	0.0271 (15)	−0.0110 (12)	−0.0010 (11)	−0.0089 (13)
C4	0.0257 (14)	0.0394 (17)	0.0210 (14)	−0.0141 (13)	0.0013 (11)	−0.0102 (12)
C5	0.0228 (13)	0.0294 (14)	0.0161 (12)	−0.0088 (11)	−0.0029 (10)	−0.0063 (11)
C6	0.0182 (12)	0.0199 (12)	0.0147 (11)	−0.0071 (10)	−0.0038 (9)	−0.0026 (9)
C7	0.0196 (12)	0.0174 (12)	0.0169 (12)	−0.0059 (10)	−0.0055 (9)	−0.0046 (9)
C8	0.0210 (12)	0.0212 (13)	0.0228 (13)	−0.0086 (10)	−0.0065 (10)	−0.0029 (10)
C9	0.0153 (11)	0.0247 (13)	0.0187 (12)	−0.0040 (10)	−0.0063 (9)	−0.0060 (10)
C10	0.0191 (12)	0.0350 (15)	0.0222 (13)	−0.0129 (11)	−0.0027 (10)	−0.0083 (12)
C11	0.0211 (13)	0.054 (2)	0.0215 (14)	−0.0184 (14)	0.0009 (11)	−0.0130 (14)
C12	0.0198 (13)	0.0466 (18)	0.0260 (15)	−0.0042 (13)	−0.0041 (11)	−0.0176 (14)
C13	0.0314 (15)	0.0264 (15)	0.0288 (15)	−0.0011 (12)	−0.0084 (12)	−0.0124 (12)
C14	0.0249 (13)	0.0256 (14)	0.0211 (13)	−0.0072 (11)	−0.0046 (10)	−0.0068 (11)
C15	0.0177 (12)	0.0240 (13)	0.0181 (12)	−0.0081 (10)	−0.0014 (9)	−0.0080 (10)
C16	0.0250 (13)	0.0317 (15)	0.0224 (13)	−0.0118 (12)	−0.0052 (11)	−0.0089 (12)
C17	0.0334 (16)	0.0384 (17)	0.0280 (15)	−0.0209 (14)	−0.0007 (12)	−0.0146 (13)
C18	0.0249 (14)	0.0471 (18)	0.0237 (14)	−0.0149 (13)	−0.0040 (11)	−0.0153 (13)
C19	0.0263 (14)	0.0367 (17)	0.0303 (16)	−0.0055 (13)	−0.0131 (12)	−0.0080 (13)
C20	0.0242 (14)	0.0264 (14)	0.0295 (15)	−0.0054 (11)	−0.0106 (11)	−0.0089 (12)
I1'	0.04789 (13)	0.04025 (12)	0.02762 (11)	−0.02840 (10)	−0.00919 (9)	−0.00140 (9)
O1'	0.0276 (10)	0.0228 (10)	0.0267 (10)	−0.0111 (8)	0.0004 (8)	−0.0114 (8)
C1'	0.0239 (13)	0.0226 (13)	0.0178 (12)	−0.0106 (11)	−0.0045 (10)	−0.0054 (10)
C2'	0.0231 (13)	0.0277 (14)	0.0253 (14)	−0.0119 (11)	−0.0034 (11)	−0.0070 (11)
C3'	0.0236 (14)	0.0333 (16)	0.0356 (17)	−0.0095 (12)	−0.0092 (12)	−0.0064 (13)
C4'	0.0323 (15)	0.0389 (17)	0.0255 (15)	−0.0156 (13)	−0.0140 (12)	−0.0026 (13)
C5'	0.0287 (14)	0.0316 (15)	0.0187 (13)	−0.0120 (12)	−0.0084 (11)	−0.0028 (11)
C6'	0.0228 (12)	0.0205 (12)	0.0164 (12)	−0.0098 (10)	−0.0043 (10)	−0.0054 (10)
C7'	0.0220 (12)	0.0170 (12)	0.0178 (12)	−0.0071 (10)	−0.0050 (10)	−0.0038 (10)
C8'	0.0238 (13)	0.0207 (13)	0.0243 (13)	−0.0077 (11)	−0.0044 (11)	−0.0059 (11)
C9'	0.0204 (12)	0.0217 (13)	0.0168 (12)	−0.0080 (10)	−0.0079 (10)	0.0003 (10)
C10'	0.0272 (14)	0.0217 (13)	0.0193 (13)	−0.0082 (11)	−0.0047 (10)	−0.0008 (10)
C11'	0.0246 (14)	0.0322 (15)	0.0232 (14)	−0.0079 (12)	−0.0044 (11)	−0.0069 (12)
C12'	0.0301 (15)	0.0488 (19)	0.0180 (13)	−0.0184 (14)	−0.0041 (11)	−0.0018 (13)
C13'	0.0483 (19)	0.0392 (18)	0.0256 (16)	−0.0266 (16)	−0.0056 (14)	0.0037 (13)
C14'	0.0421 (17)	0.0270 (15)	0.0247 (15)	−0.0193 (13)	−0.0089 (13)	−0.0004 (12)
C15'	0.0212 (12)	0.0192 (12)	0.0183 (12)	−0.0051 (10)	−0.0035 (10)	−0.0069 (10)
C16'	0.0264 (14)	0.0330 (15)	0.0233 (14)	−0.0133 (12)	−0.0041 (11)	−0.0048 (12)
C17'	0.0239 (14)	0.0474 (19)	0.0316 (16)	−0.0135 (14)	−0.0066 (12)	−0.0103 (14)
C18'	0.0244 (14)	0.0414 (18)	0.0288 (16)	−0.0018 (13)	−0.0119 (12)	−0.0084 (14)
C19'	0.0318 (15)	0.0249 (14)	0.0243 (14)	−0.0032 (12)	−0.0114 (12)	−0.0023 (11)
C20'	0.0259 (13)	0.0242 (13)	0.0199 (13)	−0.0081 (11)	−0.0073 (10)	−0.0038 (11)

I1—C2	2.175 (3)	I1'—C2'	2.183 (3)
O1—C8	1.421 (3)	O1'—C8'	1.439 (3)
O1—C1	1.442 (3)	O1'—C1'	1.444 (3)
C1—C2	1.518 (4)	C1'—C2'	1.522 (4)
C1—C6	1.534 (4)	C1'—C6'	1.534 (3)
C1—H1	1.0000	C1'—H1'	1.0000
C2—C3	1.514 (4)	C2'—C3'	1.515 (4)
C2—H2	1.0000	C2'—H2'	1.0000
C3—C4	1.524 (4)	C3'—C4'	1.523 (4)
C3—H3A	0.9900	C3'—H3'1	0.9900
C3—H3B	0.9900	C3'—H3'2	0.9900
C4—C5	1.528 (4)	C4'—C5'	1.526 (4)
C4—H4A	0.9900	C4'—H4'1	0.9900
C4—H4B	0.9900	C4'—H4'2	0.9900
C5—C6	1.536 (3)	C5'—C6'	1.535 (4)
C5—H5A	0.9900	C5'—H5'1	0.9900
C5—H5B	0.9900	C5'—H5'2	0.9900
C6—C7	1.556 (3)	C6'—C7'	1.560 (4)
C6—H6	1.0000	C6'—H6'	1.0000
C7—C15	1.526 (4)	C7'—C9'	1.527 (4)
C7—C9	1.547 (3)	C7'—C15'	1.545 (4)
C7—C8	1.550 (4)	C7'—C8'	1.553 (4)
C8—H8A	0.9900	C8'—H8'1	0.9900
C8—H8B	0.9900	C8'—H8'2	0.9900
C9—C14	1.393 (4)	C9'—C10'	1.388 (4)
C9—C10	1.396 (4)	C9'—C14'	1.392 (4)
C10—C11	1.384 (4)	C10'—C11'	1.389 (4)
C10—H10	0.9500	C10'—H10'	0.9500
C11—C12	1.370 (5)	C11'—C12'	1.386 (4)
C11—H11	0.9500	C11'—H11'	0.9500
C12—C13	1.385 (4)	C12'—C13'	1.372 (5)
C12—H12	0.9500	C12'—H12'	0.9500
C13—C14	1.385 (4)	C13'—C14'	1.392 (4)
C13—H13	0.9500	C13'—H13'	0.9500
C14—H14	0.9500	C14'—H14'	0.9500
C15—C16	1.398 (4)	C15'—C20'	1.393 (4)
C15—C20	1.399 (4)	C15'—C16'	1.401 (4)
C16—C17	1.395 (4)	C16'—C17'	1.388 (4)
C16—H16	0.9500	C16'—H16'	0.9500
C17—C18	1.380 (5)	C17'—C18'	1.388 (5)
C17—H17	0.9500	C17'—H17'	0.9500
C18—C19	1.383 (4)	C18'—C19'	1.378 (4)
C18—H18	0.9500	C18'—H18'	0.9500
C19—C20	1.386 (4)	C19'—C20'	1.396 (4)
C19—H19	0.9500	C19'—H19'	0.9500
C20—H20	0.9500	C20'—H20'	0.9500
C8—O1—C1	110.04 (19)	C8'—O1'—C1'	109.76 (19)
O1—C1—C2	107.4 (2)	O1'—C1'—C2'	107.0 (2)
O1—C1—C6	104.0 (2)	O1'—C1'—C6'	104.5 (2)
C2—C1—C6	116.3 (2)	C2'—C1'—C6'	116.3 (2)
O1—C1—H1	109.6	O1'—C1'—H1'	109.6
C2—C1—H1	109.6	C2'—C1'—H1'	109.6
C6—C1—H1	109.6	C6'—C1'—H1'	109.6
C3—C2—C1	114.5 (2)	C3'—C2'—C1'	114.1 (2)
C3—C2—I1	110.48 (19)	C3'—C2'—I1'	110.34 (19)
C1—C2—I1	107.01 (17)	C1'—C2'—I1'	107.33 (18)
C3—C2—H2	108.2	C3'—C2'—H2'	108.3
C1—C2—H2	108.2	C1'—C2'—H2'	108.3
I1—C2—H2	108.2	I1'—C2'—H2'	108.3
C2—C3—C4	111.7 (2)	C2'—C3'—C4'	112.0 (2)
C2—C3—H3A	109.3	C2'—C3'—H3'1	109.2
C4—C3—H3A	109.3	C4'—C3'—H3'1	109.2
C2—C3—H3B	109.3	C2'—C3'—H3'2	109.2
C4—C3—H3B	109.3	C4'—C3'—H3'2	109.2
H3A—C3—H3B	108.0	H3'1—C3'—H3'2	107.9
C3—C4—C5	110.1 (2)	C3'—C4'—C5'	110.2 (2)
C3—C4—H4A	109.6	C3'—C4'—H4'1	109.6
C5—C4—H4A	109.6	C5'—C4'—H4'1	109.6
C3—C4—H4B	109.6	C3'—C4'—H4'2	109.6
C5—C4—H4B	109.6	C5'—C4'—H4'2	109.6
H4A—C4—H4B	108.2	H4'1—C4'—H4'2	108.1
C4—C5—C6	113.5 (2)	C4'—C5'—C6'	113.6 (2)
C4—C5—H5A	108.9	C4'—C5'—H5'1	108.8
C6—C5—H5A	108.9	C6'—C5'—H5'1	108.8
C4—C5—H5B	108.9	C4'—C5'—H5'2	108.8
C6—C5—H5B	108.9	C6'—C5'—H5'2	108.8
H5A—C5—H5B	107.7	H5'1—C5'—H5'2	107.7
C1—C6—C5	112.9 (2)	C1'—C6'—C5'	112.9 (2)
C1—C6—C7	100.37 (19)	C1'—C6'—C7'	100.5 (2)
C5—C6—C7	111.6 (2)	C5'—C6'—C7'	111.4 (2)
C1—C6—H6	110.5	C1'—C6'—H6'	110.6
C5—C6—H6	110.5	C5'—C6'—H6'	110.6
C7—C6—H6	110.5	C7'—C6'—H6'	110.6
C15—C7—C9	108.0 (2)	C9'—C7'—C15'	107.4 (2)
C15—C7—C8	114.7 (2)	C9'—C7'—C8'	113.8 (2)
C9—C7—C8	109.6 (2)	C15'—C7'—C8'	109.0 (2)
C15—C7—C6	112.9 (2)	C9'—C7'—C6'	113.4 (2)
C9—C7—C6	113.0 (2)	C15'—C7'—C6'	113.6 (2)
C8—C7—C6	98.61 (19)	C8'—C7'—C6'	99.6 (2)
O1—C8—C7	106.6 (2)	O1'—C8'—C7'	106.6 (2)
O1—C8—H8A	110.4	O1'—C8'—H8'1	110.4
C7—C8—H8A	110.4	C7'—C8'—H8'1	110.4
O1—C8—H8B	110.4	O1'—C8'—H8'2	110.4
C7—C8—H8B	110.4	C7'—C8'—H8'2	110.4
H8A—C8—H8B	108.6	H8'1—C8'—H8'2	108.6
C14—C9—C10	117.0 (2)	C10'—C9'—C14'	118.3 (3)
C14—C9—C7	124.0 (2)	C10'—C9'—C7'	118.9 (2)
C10—C9—C7	118.9 (2)	C14'—C9'—C7'	122.8 (2)
C11—C10—C9	121.9 (3)	C9'—C10'—C11'	121.4 (3)
C11—C10—H10	119.0	C9'—C10'—H10'	119.3
C9—C10—H10	119.0	C11'—C10'—H10'	119.3
C12—C11—C10	119.9 (3)	C12'—C11'—C10'	119.6 (3)
C12—C11—H11	120.1	C12'—C11'—H11'	120.2
C10—C11—H11	120.1	C10'—C11'—H11'	120.2
C11—C12—C13	119.8 (3)	C13'—C12'—C11'	119.6 (3)
C11—C12—H12	120.1	C13'—C12'—H12'	120.2
C13—C12—H12	120.1	C11'—C12'—H12'	120.2
C14—C13—C12	120.2 (3)	C12'—C13'—C14'	120.8 (3)
C14—C13—H13	119.9	C12'—C13'—H13'	119.6
C12—C13—H13	119.9	C14'—C13'—H13'	119.6
C13—C14—C9	121.3 (3)	C9'—C14'—C13'	120.2 (3)
C13—C14—H14	119.4	C9'—C14'—H14'	119.9
C9—C14—H14	119.4	C13'—C14'—H14'	119.9
C16—C15—C20	117.9 (3)	C20'—C15'—C16'	117.7 (3)
C16—C15—C7	123.5 (2)	C20'—C15'—C7'	124.2 (2)
C20—C15—C7	118.7 (2)	C16'—C15'—C7'	118.1 (2)
C17—C16—C15	120.5 (3)	C17'—C16'—C15'	121.5 (3)
C17—C16—H16	119.7	C17'—C16'—H16'	119.2
C15—C16—H16	119.7	C15'—C16'—H16'	119.2
C18—C17—C16	120.6 (3)	C18'—C17'—C16'	119.7 (3)
C18—C17—H17	119.7	C18'—C17'—H17'	120.1
C16—C17—H17	119.7	C16'—C17'—H17'	120.1
C17—C18—C19	119.5 (3)	C19'—C18'—C17'	119.7 (3)
C17—C18—H18	120.2	C19'—C18'—H18'	120.1
C19—C18—H18	120.2	C17'—C18'—H18'	120.1
C18—C19—C20	120.2 (3)	C18'—C19'—C20'	120.5 (3)
C18—C19—H19	119.9	C18'—C19'—H19'	119.8
C20—C19—H19	119.9	C20'—C19'—H19'	119.8
C19—C20—C15	121.3 (3)	C15'—C20'—C19'	120.8 (3)
C19—C20—H20	119.4	C15'—C20'—H20'	119.6
C15—C20—H20	119.4	C19'—C20'—H20'	119.6
C8—O1—C1—C2	−143.3 (2)	C8'—O1'—C1'—C2'	145.4 (2)
C8—O1—C1—C6	−19.5 (3)	C8'—O1'—C1'—C6'	21.4 (3)
O1—C1—C2—C3	74.7 (3)	O1'—C1'—C2'—C3'	−74.9 (3)
C6—C1—C2—C3	−41.2 (3)	C6'—C1'—C2'—C3'	41.4 (3)
O1—C1—C2—I1	−162.47 (16)	O1'—C1'—C2'—I1'	162.51 (16)
C6—C1—C2—I1	81.6 (2)	C6'—C1'—C2'—I1'	−81.2 (2)
C1—C2—C3—C4	50.6 (3)	C1'—C2'—C3'—C4'	−50.7 (3)
I1—C2—C3—C4	−70.3 (3)	I1'—C2'—C3'—C4'	70.2 (3)
C2—C3—C4—C5	−58.0 (3)	C2'—C3'—C4'—C5'	57.8 (3)
C3—C4—C5—C6	56.8 (3)	C3'—C4'—C5'—C6'	−56.4 (3)
O1—C1—C6—C5	−79.3 (2)	O1'—C1'—C6'—C5'	79.0 (3)
C2—C1—C6—C5	38.5 (3)	C2'—C1'—C6'—C5'	−38.7 (3)
O1—C1—C6—C7	39.7 (2)	O1'—C1'—C6'—C7'	−39.8 (2)
C2—C1—C6—C7	157.5 (2)	C2'—C1'—C6'—C7'	−157.4 (2)
C4—C5—C6—C1	−46.6 (3)	C4'—C5'—C6'—C1'	46.5 (3)
C4—C5—C6—C7	−158.8 (2)	C4'—C5'—C6'—C7'	158.6 (2)
C1—C6—C7—C15	−164.5 (2)	C1'—C6'—C7'—C9'	162.8 (2)
C5—C6—C7—C15	−44.6 (3)	C5'—C6'—C7'—C9'	43.0 (3)
C1—C6—C7—C9	72.6 (2)	C1'—C6'—C7'—C15'	−74.1 (2)
C5—C6—C7—C9	−167.5 (2)	C5'—C6'—C7'—C15'	166.0 (2)
C1—C6—C7—C8	−43.0 (2)	C1'—C6'—C7'—C8'	41.6 (2)
C5—C6—C7—C8	76.9 (2)	C5'—C6'—C7'—C8'	−78.2 (2)
C1—O1—C8—C7	−9.2 (3)	C1'—O1'—C8'—C7'	6.3 (3)
C15—C7—C8—O1	153.3 (2)	C9'—C7'—C8'—O1'	−151.4 (2)
C9—C7—C8—O1	−85.2 (2)	C15'—C7'—C8'—O1'	88.8 (3)
C6—C7—C8—O1	33.1 (2)	C6'—C7'—C8'—O1'	−30.4 (3)
C15—C7—C9—C14	−109.6 (3)	C15'—C7'—C9'—C10'	−68.6 (3)
C8—C7—C9—C14	124.8 (3)	C8'—C7'—C9'—C10'	170.7 (2)
C6—C7—C9—C14	16.0 (4)	C6'—C7'—C9'—C10'	57.8 (3)
C15—C7—C9—C10	68.7 (3)	C15'—C7'—C9'—C14'	109.2 (3)
C8—C7—C9—C10	−56.9 (3)	C8'—C7'—C9'—C14'	−11.6 (4)
C6—C7—C9—C10	−165.8 (2)	C6'—C7'—C9'—C14'	−124.4 (3)
C14—C9—C10—C11	−0.4 (4)	C14'—C9'—C10'—C11'	0.3 (4)
C7—C9—C10—C11	−178.8 (2)	C7'—C9'—C10'—C11'	178.2 (3)
C9—C10—C11—C12	0.6 (4)	C9'—C10'—C11'—C12'	−0.3 (4)
C10—C11—C12—C13	−0.5 (5)	C10'—C11'—C12'—C13'	−0.4 (5)
C11—C12—C13—C14	0.2 (5)	C11'—C12'—C13'—C14'	0.9 (5)
C12—C13—C14—C9	0.1 (5)	C10'—C9'—C14'—C13'	0.3 (4)
C10—C9—C14—C13	0.0 (4)	C7'—C9'—C14'—C13'	−177.5 (3)
C7—C9—C14—C13	178.3 (3)	C12'—C13'—C14'—C9'	−0.9 (5)
C9—C7—C15—C16	−116.8 (3)	C9'—C7'—C15'—C20'	118.0 (3)
C8—C7—C15—C16	5.7 (4)	C8'—C7'—C15'—C20'	−118.3 (3)
C6—C7—C15—C16	117.6 (3)	C6'—C7'—C15'—C20'	−8.3 (3)
C9—C7—C15—C20	62.9 (3)	C9'—C7'—C15'—C16'	−61.1 (3)
C8—C7—C15—C20	−174.7 (2)	C8'—C7'—C15'—C16'	62.6 (3)
C6—C7—C15—C20	−62.7 (3)	C6'—C7'—C15'—C16'	172.6 (2)
C20—C15—C16—C17	−0.3 (4)	C20'—C15'—C16'—C17'	0.8 (4)
C7—C15—C16—C17	179.3 (2)	C7'—C15'—C16'—C17'	179.9 (3)
C15—C16—C17—C18	−0.2 (4)	C15'—C16'—C17'—C18'	−0.3 (5)
C16—C17—C18—C19	0.4 (4)	C16'—C17'—C18'—C19'	0.2 (5)
C17—C18—C19—C20	−0.1 (5)	C17'—C18'—C19'—C20'	−0.6 (5)
C18—C19—C20—C15	−0.4 (5)	C16'—C15'—C20'—C19'	−1.1 (4)
C16—C15—C20—C19	0.6 (4)	C7'—C15'—C20'—C19'	179.8 (2)
C7—C15—C20—C19	−179.0 (3)	C18'—C19'—C20'—C15'	1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1i	1.00	2.53	3.519 (3)	171
C2′—H2′···Cg2ii	1.00	2.54	3.533 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9–C14 and C15′–C20′ rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg1i	1.00	2.53	3.519 (3)	171
C2′—H2′⋯Cg2ii	1.00	2.54	3.533 (3)	171

Symmetry codes: (i) ; (ii) .