7-Iodo-3,3-diphenyl­octa­hydro­benzo­furan

Sohail, M.; Yao-Feng, W.; Qi, W.; Chen, F.-X.

doi:10.1107/S1600536813007563

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o585

doi:10.1107/S1600536813007563

Open

access

7-Iodo-3,3-diphenyloctahydrobenzofuran

Muhammad Sohail,^a Wang Yao-Feng,^a Wang Qi ^a and Fu-Xue Chen ^a ^*

^aSchool of Chemical Engineering and Environment, Beijing Institue of Technology, Beijing 100081, People's Republic of China
^*Correspondence e-mail: fuxue.chen@bit.edu.cn

(Received 8 March 2013; accepted 19 March 2013; online 23 March 2013)

The title compound, C₂₀H₂₁IO, was synthesized by cyclohaloetherification of 2-(cyclohex-2-enyl)-2,2-diphenylethanol in CH₂Cl₂, and crystallized with two independent molecules in the asymmetric unit. The six-membered cyclohexane 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, molecules are linked via pairs of C—H⋯π interactions, 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_r = 404.27
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.091
S = 1.00
9610 reflections
397 parameters
H-atom parameters constrained
Δρ_max = 1.05 e Å⁻³
Δρ_min = −0.75 e Å⁻³

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) -x+1, -y+1, -z+1; (ii) -x+2, -y+2, -z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813007563/hg5298sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813007563/hg5298Isup3.cml

checkCIF report

Comment top

The title compound (I, Fig. 1), is an important core structure of many organic drugs and natural products (Huang et al. 2007, Trost et al., 2003) and is useful to introduce functionality at C7. The asymmetric unit of title compound consists of two independent molecules in which the iodo-cyclohexane rings adopt chair conformations. In the crystal lattice, two molecules in asymmetric unit are linked by C—H···π interactions with phenyl ring.

Related literature top

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 top

N-Iodosuccinimide (13.5 mg, 0.06 mmole, 1.2 eq) was added to the solution of 2-(cyclohex-2-enyl)-2,2-diphenylethanol (13.9 mg, 0.05 mmole, 1 eq) in CH₂Cl₂ (0.5 ml) at -78°C. The reaction mixture was stirred at -78°C for 2.5 h, after reaction completion, as monitored by TLC the crude was directly loaded on column and purified by flash column chromatography (silica gel, Et₂O-Petrolium ether, 1:40), redissolving of crude in n-hexane afforded pure crystals (99%) of (I) (Brooner et al. 2011).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the two molecules of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A view of C—H···π interactions are indicated by dotted lines in the crystal structure of the title compound.

7-Iodo-3,3-diphenyloctahydrobenzofuran top

Crystal data top

C₂₀H₂₁IO	Z = 4
M_r = 404.27	F(000) = 808
Triclinic, P1	D_x = 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

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	9610 independent reflections
Radiation source: Rotating Anode	7599 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 28.5714 pixels mm^-1	θ_max = 30.0°, θ_min = 2.2°
phi and ω scans	h = −16→13
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −17→16
T_min = 0.572, T_max = 0.833	l = −19→19
19455 measured reflections

Refinement top

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(F_o²) + (0.0318P)² + 1.060P] where P = (F_o² + 2F_c²)/3
9610 reflections	(Δ/σ)_max = 0.002
397 parameters	Δρ_max = 1.05 e Å⁻³
0 restraints	Δρ_min = −0.75 e Å⁻³

Crystal data top

C₂₀H₂₁IO	γ = 64.945 (7)°
M_r = 404.27	V = 1692.8 (5) Å³
Triclinic, P1	Z = 4
a = 11.4082 (18) Å	Mo Kα radiation
b = 12.523 (2) Å	µ = 1.89 mm⁻¹
c = 14.007 (3) Å	T = 153 K
α = 73.306 (8)°	0.33 × 0.27 × 0.10 mm
β = 71.646 (8)°

Data collection top

Rigaku AFC10/Saturn724+ diffractometer	9610 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	7599 reflections with I > 2σ(I)
T_min = 0.572, T_max = 0.833	R_int = 0.034
19455 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.00	Δρ_max = 1.05 e Å⁻³
9610 reflections	Δρ_min = −0.75 e Å⁻³
397 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) −x+2, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁IO
M_r	404.27
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	11.4082 (18), 12.523 (2), 14.007 (3)
α, β, γ (°)	73.306 (8), 71.646 (8), 64.945 (7)
V (Å³)	1692.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.89
Crystal size (mm)	0.33 × 0.27 × 0.10

Data collection
Diffractometer	Rigaku AFC10/Saturn724+ diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2008)
T_min, T_max	0.572, 0.833
No. of measured, independent and observed [I > 2σ(I)] reflections	19455, 9610, 7599
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.091, 1.00
No. of reflections	9610
No. of parameters	397
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.05, −0.75

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) −x+2, −y+2, −z.

Acknowledgements

Financial support from Beijing Institute of Technology is acknowledged.

References

Brooner, R. E. M. & Widenhoefer, R. A. (2011). Chem. Eur. J. 17, 6170–6178. Web of Science PubMed Google Scholar
Huang, J. & Chen, F. (2007). Helv. Chim. Acta, 90, 1366–1372. Web of Science CrossRef CAS Google Scholar
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Trost, B. M., Shen, H. C. & Surivet, J. (2003). Angew. Chem. Int. Ed. 42, 3943–3947. Web of Science CrossRef CAS Google Scholar