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The title compound, C28H30O2, was obtained by an unprecedented osmium tetraoxide-mediated dimerization of (2'-methyl-3'-oxocyclo­hex-1'-enyl)phenyl­ethane. The trans ster­eo­chemistry was revealed by X-ray crystallography. The mol­ecule exhibits a crystallographic center of inversion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801018384/dn6008sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801018384/dn6008Isup2.hkl
Contains datablock I

CCDC reference: 177195

Key indicators

  • Single-crystal X-ray study
  • T = 213 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.058
  • wR factor = 0.165
  • Data-to-parameter ratio = 11.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1996); software used to prepare material for publication: SHELXTL.

(±)-(1RS,2SR)-1,2-Di(2'-methyl-3'-oxo-cyclohex-1'-enyl)-1,2- diphenylethan top
Crystal data top
C28H30O2Dx = 1.192 Mg m3
Mr = 398.52Melting point: 230 K
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 10.8658 (7) ÅCell parameters from 25 reflections
b = 9.4435 (5) Åθ = 40.3–46.2°
c = 11.7323 (8) ŵ = 0.57 mm1
β = 112.740 (6)°T = 213 K
V = 1110.29 (12) Å3Prism, colourless
Z = 20.50 × 0.50 × 0.20 mm
F(000) = 428
Data collection top
Enraf-Nonius CAD-4
diffractometer
1794 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 69.9°, θmin = 4.7°
ω scansh = 013
Absorption correction: ψ scan
(SHELXTL; Sheldrick, 1996)
k = 110
Tmin = 0.765, Tmax = 0.895l = 1413
2229 measured reflections2 standard reflections every 120 min
2116 independent reflections intensity decay: 3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.165 w = 1/[σ2(Fo2) + (0.0912P)2 + 0.2417P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2116 reflectionsΔρmax = 0.22 e Å3
187 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0092 (16)
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*/UeqOcc. (<1)
C10.01485 (18)0.41991 (19)0.98823 (17)0.0542 (5)
H10.0295 (19)0.370 (2)1.0693 (19)0.056 (5)*
C1'0.04892 (18)0.35902 (19)0.90364 (16)0.0535 (5)
C2'0.12380 (17)0.24016 (19)0.93175 (16)0.0548 (5)
C3'0.1894 (2)0.1909 (2)0.84903 (18)0.0634 (5)
C4'0.1689 (3)0.2736 (3)0.7343 (2)0.0748 (6)
H4'A0.241 (3)0.348 (3)0.761 (3)0.100 (9)*
H4'B0.183 (3)0.206 (3)0.675 (3)0.101 (9)*
C5'0.0344 (2)0.3460 (3)0.68447 (19)0.0666 (6)
H5'A0.039 (2)0.272 (3)0.656 (2)0.071 (6)*
H5'B0.027 (3)0.405 (3)0.612 (3)0.085 (7)*
C6'0.0206 (2)0.4386 (2)0.78447 (17)0.0588 (5)
H6'A0.072 (2)0.477 (2)0.7529 (19)0.059 (5)*
H6'B0.082 (2)0.522 (3)0.802 (2)0.075 (6)*
C7'0.1524 (2)0.1514 (2)1.04554 (19)0.0647 (5)
H7'10.20210.06781.04100.071 (6)*0.50
H7'20.06900.12311.05090.071 (6)*0.50
H7'30.20450.20611.11820.071 (6)*0.50
H7'40.11500.19691.09900.071 (6)*0.50
H7'50.24810.14161.08920.071 (6)*0.50
H7'60.11260.05851.02180.071 (6)*0.50
C1"0.16390 (18)0.3858 (2)0.93855 (16)0.0558 (5)
C2"0.2035 (2)0.2575 (2)0.97249 (19)0.0632 (5)
H2"0.133 (2)0.197 (3)1.032 (2)0.077 (7)*
C3"0.3358 (2)0.2183 (3)0.9293 (2)0.0718 (6)
H3"0.359 (3)0.122 (3)0.954 (2)0.092 (8)*
C4"0.4328 (2)0.3059 (3)0.8511 (2)0.0746 (6)
H4"0.526 (3)0.276 (3)0.820 (2)0.082 (7)*
C5"0.3961 (2)0.4339 (3)0.8167 (2)0.0760 (6)
H5"0.460 (3)0.496 (3)0.759 (2)0.086 (7)*
C6"0.2626 (2)0.4735 (2)0.85927 (19)0.0649 (5)
H6"0.237 (2)0.564 (3)0.833 (2)0.082 (7)*
O3'0.26178 (18)0.08671 (19)0.87563 (16)0.0877 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0585 (10)0.0504 (10)0.0457 (9)0.0044 (7)0.0115 (7)0.0014 (7)
C1'0.0557 (10)0.0500 (9)0.0468 (9)0.0006 (7)0.0111 (7)0.0009 (7)
C2'0.0547 (9)0.0509 (10)0.0491 (9)0.0010 (7)0.0094 (7)0.0013 (7)
C3'0.0610 (10)0.0621 (11)0.0580 (11)0.0065 (9)0.0130 (8)0.0025 (9)
C4'0.0815 (15)0.0804 (16)0.0663 (13)0.0173 (12)0.0328 (11)0.0059 (11)
C5'0.0766 (13)0.0692 (13)0.0504 (10)0.0081 (10)0.0205 (9)0.0012 (9)
C6'0.0658 (12)0.0557 (11)0.0488 (10)0.0057 (9)0.0154 (8)0.0030 (8)
C7'0.0704 (12)0.0545 (11)0.0604 (11)0.0088 (9)0.0156 (9)0.0075 (9)
C1"0.0601 (10)0.0558 (10)0.0458 (9)0.0015 (8)0.0142 (8)0.0061 (8)
C2"0.0684 (12)0.0602 (11)0.0557 (10)0.0027 (9)0.0181 (9)0.0034 (9)
C3"0.0752 (13)0.0727 (14)0.0666 (12)0.0147 (11)0.0263 (10)0.0140 (11)
C4"0.0603 (12)0.0816 (15)0.0762 (14)0.0142 (11)0.0199 (10)0.0247 (12)
C5"0.0642 (12)0.0752 (15)0.0714 (13)0.0079 (11)0.0074 (10)0.0123 (11)
C6"0.0644 (11)0.0578 (11)0.0608 (11)0.0003 (9)0.0112 (9)0.0066 (9)
O3'0.0996 (12)0.0833 (11)0.0787 (10)0.0378 (9)0.0329 (9)0.0092 (8)
Geometric parameters (Å, º) top
C1—C1'1.525 (3)C7'—H7'10.9700
C1—C1"1.529 (3)C7'—H7'20.9700
C1—C1i1.549 (4)C7'—H7'30.9700
C1—H11.00 (2)C7'—H7'40.9700
C1'—C2'1.350 (3)C7'—H7'50.9700
C1'—C6'1.511 (3)C7'—H7'60.9700
C2'—C3'1.484 (3)C1"—C6"1.389 (3)
C2'—C7'1.503 (3)C1"—C2"1.394 (3)
C3'—O3'1.222 (2)C2"—C3"1.378 (3)
C3'—C4'1.496 (3)C2"—H2"0.99 (2)
C4'—C5'1.511 (3)C3"—C4"1.374 (4)
C4'—H4'A1.01 (3)C3"—H3"1.02 (3)
C4'—H4'B0.99 (3)C4"—C5"1.381 (4)
C5'—C6'1.516 (3)C4"—H4"0.97 (3)
C5'—H5'A1.01 (2)C5"—C6"1.391 (3)
C5'—H5'B1.00 (3)C5"—H5"0.96 (3)
C6'—H6'A1.00 (2)C6"—H6"0.99 (3)
C6'—H6'B1.00 (3)
C1'—C1—C1"110.69 (14)C2'—C7'—H7'3109.5
C1'—C1—C1i111.61 (19)H7'1—C7'—H7'3109.5
C1"—C1—C1i113.01 (19)H7'2—C7'—H7'3109.5
C1'—C1—H1105.6 (11)C2'—C7'—H7'4109.5
C1"—C1—H1108.3 (11)H7'1—C7'—H7'4141.1
C1i—C1—H1107.3 (12)H7'2—C7'—H7'456.3
C2'—C1'—C6'121.83 (17)H7'3—C7'—H7'456.3
C2'—C1'—C1122.47 (16)C2'—C7'—H7'5109.5
C6'—C1'—C1115.69 (15)H7'1—C7'—H7'556.3
C1'—C2'—C3'119.84 (17)H7'2—C7'—H7'5141.1
C1'—C2'—C7'125.34 (18)H7'3—C7'—H7'556.3
C3'—C2'—C7'114.79 (16)H7'4—C7'—H7'5109.5
O3'—C3'—C2'120.65 (19)C2'—C7'—H7'6109.5
O3'—C3'—C4'120.5 (2)H7'1—C7'—H7'656.3
C2'—C3'—C4'118.82 (17)H7'2—C7'—H7'656.3
C3'—C4'—C5'111.72 (19)H7'3—C7'—H7'6141.1
C3'—C4'—H4'A104.7 (17)H7'4—C7'—H7'6109.5
C5'—C4'—H4'A108.8 (17)H7'5—C7'—H7'6109.5
C3'—C4'—H4'B106.5 (17)C6"—C1"—C2"117.75 (19)
C5'—C4'—H4'B113.7 (17)C6"—C1"—C1124.02 (18)
H4'A—C4'—H4'B111 (2)C2"—C1"—C1118.21 (17)
C4'—C5'—C6'109.34 (18)C3"—C2"—C1"121.5 (2)
C4'—C5'—H5'A109.3 (13)C3"—C2"—H2"120.9 (14)
C6'—C5'—H5'A110.6 (13)C1"—C2"—H2"117.6 (14)
C4'—C5'—H5'B109.1 (15)C4"—C3"—C2"120.4 (2)
C6'—C5'—H5'B110.1 (15)C4"—C3"—H3"121.0 (16)
H5'A—C5'—H5'B108 (2)C2"—C3"—H3"118.6 (16)
C1'—C6'—C5'112.56 (17)C3"—C4"—C5"119.3 (2)
C1'—C6'—H6'A109.9 (12)C3"—C4"—H4"119.7 (15)
C5'—C6'—H6'A108.0 (12)C5"—C4"—H4"121.0 (15)
C1'—C6'—H6'B108.8 (13)C4"—C5"—C6"120.6 (2)
C5'—C6'—H6'B110.5 (14)C4"—C5"—H5"122.2 (16)
H6'A—C6'—H6'B106.8 (18)C6"—C5"—H5"117.0 (16)
C2'—C7'—H7'1109.5C1"—C6"—C5"120.6 (2)
C2'—C7'—H7'2109.5C1"—C6"—H6"119.1 (15)
H7'1—C7'—H7'2109.5C5"—C6"—H6"120.4 (14)
C1"—C1—C1'—C2'103.0 (2)C2'—C1'—C6'—C5'22.8 (3)
C1i—C1—C1'—C2'130.2 (2)C1—C1'—C6'—C5'155.93 (18)
C1"—C1—C1'—C6'75.7 (2)C4'—C5'—C6'—C1'52.5 (3)
C1i—C1—C1'—C6'51.1 (2)C1'—C1—C1"—C6"91.4 (2)
C6'—C1'—C2'—C3'4.8 (3)C1i—C1—C1"—C6"34.6 (3)
C1—C1'—C2'—C3'176.53 (16)C1'—C1—C1"—C2"87.2 (2)
C6'—C1'—C2'—C7'177.46 (18)C1i—C1—C1"—C2"146.8 (2)
C1—C1'—C2'—C7'1.2 (3)C6"—C1"—C2"—C3"0.0 (3)
C1'—C2'—C3'—O3'177.09 (19)C1—C1"—C2"—C3"178.65 (18)
C7'—C2'—C3'—O3'0.9 (3)C1"—C2"—C3"—C4"0.1 (3)
C1'—C2'—C3'—C4'1.0 (3)C2"—C3"—C4"—C5"0.2 (3)
C7'—C2'—C3'—C4'179.0 (2)C3"—C4"—C5"—C6"0.7 (3)
O3'—C3'—C4'—C5'151.8 (2)C2"—C1"—C6"—C5"0.5 (3)
C2'—C3'—C4'—C5'30.1 (3)C1—C1"—C6"—C5"179.07 (18)
C3'—C4'—C5'—C6'55.8 (3)C4"—C5"—C6"—C1"0.9 (3)
Symmetry code: (i) x, y+1, z+2.
 

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