organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

7-Iodo-3,3-di­phenyl­octa­hydro­benzo­furan

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[Huang, J. & Chen, F. (2007). Helv. Chim. Acta, 90, 1366-1372.]); Trost et al. (2003[Trost, B. M., Shen, H. C. & Surivet, J. (2003). Angew. Chem. Int. Ed. 42, 3943-3947.]). For the synthesis of 2-(cyclo­hex-2-en­yl)-2,2-diphenyl­ethanol, see: Brooner & Widenhoefer (2011[Brooner, R. E. M. & Widenhoefer, R. A. (2011). Chem. Eur. J. 17, 6170-6178.]).

[Scheme 1]

Experimental

Crystal data
  • C20H21IO

  • Mr = 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[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.572, Tmax = 0.833

  • 19455 measured reflections

  • 9610 independent reflections

  • 7599 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 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

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 DA 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[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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).

Refinement top

Carbon protons were included in the riding model approximation with C—H distances 0.95-1.00 Å, and with Uiso(H)=1.2Ueq(C).

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
[Figure 1] Fig. 1. The molecular structure of the two molecules of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] 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
C20H21IOZ = 4
Mr = 404.27F(000) = 808
Triclinic, P1Dx = 1.586 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.4082 (18) ÅCell parameters from 5864 reflections
b = 12.523 (2) Åθ = 2.2–30.0°
c = 14.007 (3) ŵ = 1.89 mm1
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 Anode7599 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
Detector resolution: 28.5714 pixels mm-1θmax = 30.0°, θmin = 2.2°
phi and ω scansh = 1613
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2008)
k = 1716
Tmin = 0.572, Tmax = 0.833l = 1919
19455 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H-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 parametersΔρmax = 1.05 e Å3
0 restraintsΔρmin = 0.75 e Å3
Crystal data top
C20H21IOγ = 64.945 (7)°
Mr = 404.27V = 1692.8 (5) Å3
Triclinic, P1Z = 4
a = 11.4082 (18) ÅMo Kα radiation
b = 12.523 (2) ŵ = 1.89 mm1
c = 14.007 (3) ÅT = 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)
Tmin = 0.572, Tmax = 0.833Rint = 0.034
19455 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.091H-atom parameters constrained
S = 1.00Δρmax = 1.05 e Å3
9610 reflectionsΔρmin = 0.75 e Å3
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
xyzUiso*/Ueq
I10.65947 (2)0.703016 (18)0.295052 (16)0.03449 (6)
O10.53230 (19)0.40425 (16)0.40367 (15)0.0228 (4)
C10.5264 (2)0.5248 (2)0.3578 (2)0.0184 (5)
H10.47760.57770.41030.022*
C20.6681 (3)0.5206 (2)0.3193 (2)0.0216 (5)
H20.71770.47100.37430.026*
C30.7423 (3)0.4681 (3)0.2228 (2)0.0278 (6)
H3A0.76110.38090.23880.033*
H3B0.82830.47960.19730.033*
C40.6631 (3)0.5265 (3)0.1397 (2)0.0285 (6)
H4A0.71330.48890.07840.034*
H4B0.64930.61270.12010.034*
C50.5288 (3)0.5116 (3)0.1782 (2)0.0228 (5)
H5A0.54380.42530.19130.027*
H5B0.47780.55230.12400.027*
C60.4460 (2)0.5624 (2)0.27622 (19)0.0176 (5)
H60.40370.65170.26010.021*
C70.3390 (2)0.5062 (2)0.33450 (19)0.0176 (5)
C80.4302 (3)0.3834 (2)0.3831 (2)0.0212 (5)
H8A0.37920.35000.44720.025*
H8B0.46860.32600.33550.025*
C90.2348 (2)0.5739 (2)0.4198 (2)0.0196 (5)
C100.1516 (3)0.5193 (3)0.4926 (2)0.0241 (6)
H100.16190.44110.48910.029*
C110.0547 (3)0.5757 (3)0.5698 (2)0.0304 (7)
H110.00010.53600.61870.036*
C120.0376 (3)0.6890 (3)0.5754 (2)0.0314 (7)
H120.02940.72830.62790.038*
C130.1182 (3)0.7460 (3)0.5043 (2)0.0302 (7)
H130.10670.82440.50820.036*
C140.2156 (3)0.6888 (3)0.4276 (2)0.0241 (6)
H140.27040.72880.37940.029*
C150.2651 (2)0.4991 (2)0.2641 (2)0.0195 (5)
C160.2684 (3)0.3913 (3)0.2510 (2)0.0250 (6)
H160.31940.31750.28640.030*
C170.1972 (3)0.3913 (3)0.1862 (2)0.0300 (7)
H170.20040.31740.17770.036*
C180.1223 (3)0.4975 (3)0.1342 (2)0.0296 (6)
H180.07360.49690.09050.036*
C190.1185 (3)0.6049 (3)0.1461 (2)0.0311 (7)
H190.06710.67830.11040.037*
C200.1893 (3)0.6057 (3)0.2100 (2)0.0260 (6)
H200.18630.68000.21720.031*
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)
H1'0.98831.07560.05810.024*
C2'1.1807 (3)1.0044 (3)0.0810 (2)0.0245 (6)
H2'1.22520.95330.02700.029*
C3'1.2537 (3)0.9465 (3)0.1671 (2)0.0305 (7)
H3'11.34350.95020.14260.037*
H3'21.26390.86100.18750.037*
C4'1.1806 (3)1.0078 (3)0.2598 (2)0.0301 (6)
H4'11.17571.09180.24110.036*
H4'21.23000.96630.31500.036*
C5'1.0407 (3)1.0052 (3)0.2979 (2)0.0256 (6)
H5'10.99391.04830.35630.031*
H5'21.04710.92100.32300.031*
C6'0.9582 (3)1.0620 (2)0.21581 (19)0.0187 (5)
H6'0.92381.15140.20630.022*
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)
H8'10.95210.83060.26860.027*
H8'20.86170.86800.18780.027*
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)
H10'0.72221.18680.35460.029*
C11'0.6425 (3)1.1161 (3)0.4972 (2)0.0273 (6)
H11'0.60471.18790.52420.033*
C12'0.6277 (3)1.0117 (3)0.5583 (2)0.0322 (7)
H12'0.58031.01160.62760.039*
C13'0.6820 (3)0.9087 (3)0.5183 (2)0.0368 (7)
H13'0.67070.83760.56000.044*
C14'0.7535 (3)0.9072 (3)0.4174 (2)0.0295 (6)
H14'0.79160.83490.39110.035*
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)
H16'0.63510.97810.23310.032*
C17'0.5377 (3)1.1134 (3)0.1324 (2)0.0333 (7)
H17'0.47081.08360.13980.040*
C18'0.5376 (3)1.2199 (3)0.0662 (2)0.0332 (7)
H18'0.47041.26340.02830.040*
C19'0.6352 (3)1.2623 (3)0.0557 (2)0.0288 (6)
H19'0.63561.33480.01000.035*
C20'0.7336 (3)1.1995 (2)0.1118 (2)0.0232 (6)
H20'0.79951.23040.10470.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.04589 (13)0.03359 (11)0.03171 (11)0.02655 (10)0.00455 (9)0.00285 (9)
O10.0265 (10)0.0197 (9)0.0248 (10)0.0122 (8)0.0108 (8)0.0038 (8)
C10.0200 (12)0.0202 (12)0.0166 (12)0.0102 (10)0.0033 (9)0.0018 (10)
C20.0205 (12)0.0250 (13)0.0213 (13)0.0099 (11)0.0060 (10)0.0033 (11)
C30.0201 (13)0.0360 (16)0.0271 (15)0.0110 (12)0.0010 (11)0.0089 (13)
C40.0257 (14)0.0394 (17)0.0210 (14)0.0141 (13)0.0013 (11)0.0102 (12)
C50.0228 (13)0.0294 (14)0.0161 (12)0.0088 (11)0.0029 (10)0.0063 (11)
C60.0182 (12)0.0199 (12)0.0147 (11)0.0071 (10)0.0038 (9)0.0026 (9)
C70.0196 (12)0.0174 (12)0.0169 (12)0.0059 (10)0.0055 (9)0.0046 (9)
C80.0210 (12)0.0212 (13)0.0228 (13)0.0086 (10)0.0065 (10)0.0029 (10)
C90.0153 (11)0.0247 (13)0.0187 (12)0.0040 (10)0.0063 (9)0.0060 (10)
C100.0191 (12)0.0350 (15)0.0222 (13)0.0129 (11)0.0027 (10)0.0083 (12)
C110.0211 (13)0.054 (2)0.0215 (14)0.0184 (14)0.0009 (11)0.0130 (14)
C120.0198 (13)0.0466 (18)0.0260 (15)0.0042 (13)0.0041 (11)0.0176 (14)
C130.0314 (15)0.0264 (15)0.0288 (15)0.0011 (12)0.0084 (12)0.0124 (12)
C140.0249 (13)0.0256 (14)0.0211 (13)0.0072 (11)0.0046 (10)0.0068 (11)
C150.0177 (12)0.0240 (13)0.0181 (12)0.0081 (10)0.0014 (9)0.0080 (10)
C160.0250 (13)0.0317 (15)0.0224 (13)0.0118 (12)0.0052 (11)0.0089 (12)
C170.0334 (16)0.0384 (17)0.0280 (15)0.0209 (14)0.0007 (12)0.0146 (13)
C180.0249 (14)0.0471 (18)0.0237 (14)0.0149 (13)0.0040 (11)0.0153 (13)
C190.0263 (14)0.0367 (17)0.0303 (16)0.0055 (13)0.0131 (12)0.0080 (13)
C200.0242 (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—C22.175 (3)I1'—C2'2.183 (3)
O1—C81.421 (3)O1'—C8'1.439 (3)
O1—C11.442 (3)O1'—C1'1.444 (3)
C1—C21.518 (4)C1'—C2'1.522 (4)
C1—C61.534 (4)C1'—C6'1.534 (3)
C1—H11.0000C1'—H1'1.0000
C2—C31.514 (4)C2'—C3'1.515 (4)
C2—H21.0000C2'—H2'1.0000
C3—C41.524 (4)C3'—C4'1.523 (4)
C3—H3A0.9900C3'—H3'10.9900
C3—H3B0.9900C3'—H3'20.9900
C4—C51.528 (4)C4'—C5'1.526 (4)
C4—H4A0.9900C4'—H4'10.9900
C4—H4B0.9900C4'—H4'20.9900
C5—C61.536 (3)C5'—C6'1.535 (4)
C5—H5A0.9900C5'—H5'10.9900
C5—H5B0.9900C5'—H5'20.9900
C6—C71.556 (3)C6'—C7'1.560 (4)
C6—H61.0000C6'—H6'1.0000
C7—C151.526 (4)C7'—C9'1.527 (4)
C7—C91.547 (3)C7'—C15'1.545 (4)
C7—C81.550 (4)C7'—C8'1.553 (4)
C8—H8A0.9900C8'—H8'10.9900
C8—H8B0.9900C8'—H8'20.9900
C9—C141.393 (4)C9'—C10'1.388 (4)
C9—C101.396 (4)C9'—C14'1.392 (4)
C10—C111.384 (4)C10'—C11'1.389 (4)
C10—H100.9500C10'—H10'0.9500
C11—C121.370 (5)C11'—C12'1.386 (4)
C11—H110.9500C11'—H11'0.9500
C12—C131.385 (4)C12'—C13'1.372 (5)
C12—H120.9500C12'—H12'0.9500
C13—C141.385 (4)C13'—C14'1.392 (4)
C13—H130.9500C13'—H13'0.9500
C14—H140.9500C14'—H14'0.9500
C15—C161.398 (4)C15'—C20'1.393 (4)
C15—C201.399 (4)C15'—C16'1.401 (4)
C16—C171.395 (4)C16'—C17'1.388 (4)
C16—H160.9500C16'—H16'0.9500
C17—C181.380 (5)C17'—C18'1.388 (5)
C17—H170.9500C17'—H17'0.9500
C18—C191.383 (4)C18'—C19'1.378 (4)
C18—H180.9500C18'—H18'0.9500
C19—C201.386 (4)C19'—C20'1.396 (4)
C19—H190.9500C19'—H19'0.9500
C20—H200.9500C20'—H20'0.9500
C8—O1—C1110.04 (19)C8'—O1'—C1'109.76 (19)
O1—C1—C2107.4 (2)O1'—C1'—C2'107.0 (2)
O1—C1—C6104.0 (2)O1'—C1'—C6'104.5 (2)
C2—C1—C6116.3 (2)C2'—C1'—C6'116.3 (2)
O1—C1—H1109.6O1'—C1'—H1'109.6
C2—C1—H1109.6C2'—C1'—H1'109.6
C6—C1—H1109.6C6'—C1'—H1'109.6
C3—C2—C1114.5 (2)C3'—C2'—C1'114.1 (2)
C3—C2—I1110.48 (19)C3'—C2'—I1'110.34 (19)
C1—C2—I1107.01 (17)C1'—C2'—I1'107.33 (18)
C3—C2—H2108.2C3'—C2'—H2'108.3
C1—C2—H2108.2C1'—C2'—H2'108.3
I1—C2—H2108.2I1'—C2'—H2'108.3
C2—C3—C4111.7 (2)C2'—C3'—C4'112.0 (2)
C2—C3—H3A109.3C2'—C3'—H3'1109.2
C4—C3—H3A109.3C4'—C3'—H3'1109.2
C2—C3—H3B109.3C2'—C3'—H3'2109.2
C4—C3—H3B109.3C4'—C3'—H3'2109.2
H3A—C3—H3B108.0H3'1—C3'—H3'2107.9
C3—C4—C5110.1 (2)C3'—C4'—C5'110.2 (2)
C3—C4—H4A109.6C3'—C4'—H4'1109.6
C5—C4—H4A109.6C5'—C4'—H4'1109.6
C3—C4—H4B109.6C3'—C4'—H4'2109.6
C5—C4—H4B109.6C5'—C4'—H4'2109.6
H4A—C4—H4B108.2H4'1—C4'—H4'2108.1
C4—C5—C6113.5 (2)C4'—C5'—C6'113.6 (2)
C4—C5—H5A108.9C4'—C5'—H5'1108.8
C6—C5—H5A108.9C6'—C5'—H5'1108.8
C4—C5—H5B108.9C4'—C5'—H5'2108.8
C6—C5—H5B108.9C6'—C5'—H5'2108.8
H5A—C5—H5B107.7H5'1—C5'—H5'2107.7
C1—C6—C5112.9 (2)C1'—C6'—C5'112.9 (2)
C1—C6—C7100.37 (19)C1'—C6'—C7'100.5 (2)
C5—C6—C7111.6 (2)C5'—C6'—C7'111.4 (2)
C1—C6—H6110.5C1'—C6'—H6'110.6
C5—C6—H6110.5C5'—C6'—H6'110.6
C7—C6—H6110.5C7'—C6'—H6'110.6
C15—C7—C9108.0 (2)C9'—C7'—C15'107.4 (2)
C15—C7—C8114.7 (2)C9'—C7'—C8'113.8 (2)
C9—C7—C8109.6 (2)C15'—C7'—C8'109.0 (2)
C15—C7—C6112.9 (2)C9'—C7'—C6'113.4 (2)
C9—C7—C6113.0 (2)C15'—C7'—C6'113.6 (2)
C8—C7—C698.61 (19)C8'—C7'—C6'99.6 (2)
O1—C8—C7106.6 (2)O1'—C8'—C7'106.6 (2)
O1—C8—H8A110.4O1'—C8'—H8'1110.4
C7—C8—H8A110.4C7'—C8'—H8'1110.4
O1—C8—H8B110.4O1'—C8'—H8'2110.4
C7—C8—H8B110.4C7'—C8'—H8'2110.4
H8A—C8—H8B108.6H8'1—C8'—H8'2108.6
C14—C9—C10117.0 (2)C10'—C9'—C14'118.3 (3)
C14—C9—C7124.0 (2)C10'—C9'—C7'118.9 (2)
C10—C9—C7118.9 (2)C14'—C9'—C7'122.8 (2)
C11—C10—C9121.9 (3)C9'—C10'—C11'121.4 (3)
C11—C10—H10119.0C9'—C10'—H10'119.3
C9—C10—H10119.0C11'—C10'—H10'119.3
C12—C11—C10119.9 (3)C12'—C11'—C10'119.6 (3)
C12—C11—H11120.1C12'—C11'—H11'120.2
C10—C11—H11120.1C10'—C11'—H11'120.2
C11—C12—C13119.8 (3)C13'—C12'—C11'119.6 (3)
C11—C12—H12120.1C13'—C12'—H12'120.2
C13—C12—H12120.1C11'—C12'—H12'120.2
C14—C13—C12120.2 (3)C12'—C13'—C14'120.8 (3)
C14—C13—H13119.9C12'—C13'—H13'119.6
C12—C13—H13119.9C14'—C13'—H13'119.6
C13—C14—C9121.3 (3)C9'—C14'—C13'120.2 (3)
C13—C14—H14119.4C9'—C14'—H14'119.9
C9—C14—H14119.4C13'—C14'—H14'119.9
C16—C15—C20117.9 (3)C20'—C15'—C16'117.7 (3)
C16—C15—C7123.5 (2)C20'—C15'—C7'124.2 (2)
C20—C15—C7118.7 (2)C16'—C15'—C7'118.1 (2)
C17—C16—C15120.5 (3)C17'—C16'—C15'121.5 (3)
C17—C16—H16119.7C17'—C16'—H16'119.2
C15—C16—H16119.7C15'—C16'—H16'119.2
C18—C17—C16120.6 (3)C18'—C17'—C16'119.7 (3)
C18—C17—H17119.7C18'—C17'—H17'120.1
C16—C17—H17119.7C16'—C17'—H17'120.1
C17—C18—C19119.5 (3)C19'—C18'—C17'119.7 (3)
C17—C18—H18120.2C19'—C18'—H18'120.1
C19—C18—H18120.2C17'—C18'—H18'120.1
C18—C19—C20120.2 (3)C18'—C19'—C20'120.5 (3)
C18—C19—H19119.9C18'—C19'—H19'119.8
C20—C19—H19119.9C20'—C19'—H19'119.8
C19—C20—C15121.3 (3)C15'—C20'—C19'120.8 (3)
C19—C20—H20119.4C15'—C20'—H20'119.6
C15—C20—H20119.4C19'—C20'—H20'119.6
C8—O1—C1—C2143.3 (2)C8'—O1'—C1'—C2'145.4 (2)
C8—O1—C1—C619.5 (3)C8'—O1'—C1'—C6'21.4 (3)
O1—C1—C2—C374.7 (3)O1'—C1'—C2'—C3'74.9 (3)
C6—C1—C2—C341.2 (3)C6'—C1'—C2'—C3'41.4 (3)
O1—C1—C2—I1162.47 (16)O1'—C1'—C2'—I1'162.51 (16)
C6—C1—C2—I181.6 (2)C6'—C1'—C2'—I1'81.2 (2)
C1—C2—C3—C450.6 (3)C1'—C2'—C3'—C4'50.7 (3)
I1—C2—C3—C470.3 (3)I1'—C2'—C3'—C4'70.2 (3)
C2—C3—C4—C558.0 (3)C2'—C3'—C4'—C5'57.8 (3)
C3—C4—C5—C656.8 (3)C3'—C4'—C5'—C6'56.4 (3)
O1—C1—C6—C579.3 (2)O1'—C1'—C6'—C5'79.0 (3)
C2—C1—C6—C538.5 (3)C2'—C1'—C6'—C5'38.7 (3)
O1—C1—C6—C739.7 (2)O1'—C1'—C6'—C7'39.8 (2)
C2—C1—C6—C7157.5 (2)C2'—C1'—C6'—C7'157.4 (2)
C4—C5—C6—C146.6 (3)C4'—C5'—C6'—C1'46.5 (3)
C4—C5—C6—C7158.8 (2)C4'—C5'—C6'—C7'158.6 (2)
C1—C6—C7—C15164.5 (2)C1'—C6'—C7'—C9'162.8 (2)
C5—C6—C7—C1544.6 (3)C5'—C6'—C7'—C9'43.0 (3)
C1—C6—C7—C972.6 (2)C1'—C6'—C7'—C15'74.1 (2)
C5—C6—C7—C9167.5 (2)C5'—C6'—C7'—C15'166.0 (2)
C1—C6—C7—C843.0 (2)C1'—C6'—C7'—C8'41.6 (2)
C5—C6—C7—C876.9 (2)C5'—C6'—C7'—C8'78.2 (2)
C1—O1—C8—C79.2 (3)C1'—O1'—C8'—C7'6.3 (3)
C15—C7—C8—O1153.3 (2)C9'—C7'—C8'—O1'151.4 (2)
C9—C7—C8—O185.2 (2)C15'—C7'—C8'—O1'88.8 (3)
C6—C7—C8—O133.1 (2)C6'—C7'—C8'—O1'30.4 (3)
C15—C7—C9—C14109.6 (3)C15'—C7'—C9'—C10'68.6 (3)
C8—C7—C9—C14124.8 (3)C8'—C7'—C9'—C10'170.7 (2)
C6—C7—C9—C1416.0 (4)C6'—C7'—C9'—C10'57.8 (3)
C15—C7—C9—C1068.7 (3)C15'—C7'—C9'—C14'109.2 (3)
C8—C7—C9—C1056.9 (3)C8'—C7'—C9'—C14'11.6 (4)
C6—C7—C9—C10165.8 (2)C6'—C7'—C9'—C14'124.4 (3)
C14—C9—C10—C110.4 (4)C14'—C9'—C10'—C11'0.3 (4)
C7—C9—C10—C11178.8 (2)C7'—C9'—C10'—C11'178.2 (3)
C9—C10—C11—C120.6 (4)C9'—C10'—C11'—C12'0.3 (4)
C10—C11—C12—C130.5 (5)C10'—C11'—C12'—C13'0.4 (5)
C11—C12—C13—C140.2 (5)C11'—C12'—C13'—C14'0.9 (5)
C12—C13—C14—C90.1 (5)C10'—C9'—C14'—C13'0.3 (4)
C10—C9—C14—C130.0 (4)C7'—C9'—C14'—C13'177.5 (3)
C7—C9—C14—C13178.3 (3)C12'—C13'—C14'—C9'0.9 (5)
C9—C7—C15—C16116.8 (3)C9'—C7'—C15'—C20'118.0 (3)
C8—C7—C15—C165.7 (4)C8'—C7'—C15'—C20'118.3 (3)
C6—C7—C15—C16117.6 (3)C6'—C7'—C15'—C20'8.3 (3)
C9—C7—C15—C2062.9 (3)C9'—C7'—C15'—C16'61.1 (3)
C8—C7—C15—C20174.7 (2)C8'—C7'—C15'—C16'62.6 (3)
C6—C7—C15—C2062.7 (3)C6'—C7'—C15'—C16'172.6 (2)
C20—C15—C16—C170.3 (4)C20'—C15'—C16'—C17'0.8 (4)
C7—C15—C16—C17179.3 (2)C7'—C15'—C16'—C17'179.9 (3)
C15—C16—C17—C180.2 (4)C15'—C16'—C17'—C18'0.3 (5)
C16—C17—C18—C190.4 (4)C16'—C17'—C18'—C19'0.2 (5)
C17—C18—C19—C200.1 (5)C17'—C18'—C19'—C20'0.6 (5)
C18—C19—C20—C150.4 (5)C16'—C15'—C20'—C19'1.1 (4)
C16—C15—C20—C190.6 (4)C7'—C15'—C20'—C19'179.8 (2)
C7—C15—C20—C19179.0 (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···AD—HH···AD···AD—H···A
C2—H2···Cg1i1.002.533.519 (3)171
C2—H2···Cg2ii1.002.543.533 (3)171
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+2, z.

Experimental details

Crystal data
Chemical formulaC20H21IO
Mr404.27
Crystal system, space groupTriclinic, 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)
V3)1692.8 (5)
Z4
Radiation typeMo Kα
µ (mm1)1.89
Crystal size (mm)0.33 × 0.27 × 0.10
Data collection
DiffractometerRigaku AFC10/Saturn724+
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2008)
Tmin, Tmax0.572, 0.833
No. of measured, independent and
observed [I > 2σ(I)] reflections
19455, 9610, 7599
Rint0.034
(sin θ/λ)max1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.091, 1.00
No. of reflections9610
No. of parameters397
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
C2—H2···Cg1i1.002.533.519 (3)171
C2'—H2'···Cg2ii1.002.543.533 (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

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

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