organic compounds
cis-2-(4-Methoxyphenyl)-4-methyl-1,2-dihydronaphthalen-1-ol
aDepartment of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada, and bDepartment of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada
*Correspondence e-mail: alough@chem.utoronto.ca
The stereochemistry and regiochemistry of the title compound, C18H18O2, were determined by the X-ray analysis. There are two independent molecules in the in which the dihedral angles between the benzene rings are 88.31 (4) and 86.27 (4)°. The cyclohexene rings are in half-chair conformations. In the crystal, O—H⋯O hydrogen bonds link alternating types of molecules into chains along [010] with graph-set C22(4).
CCDC reference: 995951
Related literature
For metal-catalysed ring-opening reactions of oxanorbornadiene compounds, see: Jack et al. (2013). For hydrogen-bond graph-set notation, see: Bernstein et al. (1995).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2012); cell SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
CCDC reference: 995951
10.1107/S1600536814007739/rn2124sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814007739/rn2124Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814007739/rn2124Isup3.cml
C1 methyl substituted oxanorbornadiene (I) (0.50 mmol) and 4-methoxy-1-iodobenzene (II) (0.55 mmol) were added into an oven-dried vial containing PdCl2(PPh3)2 (0.05 mmol), Zn powder (5 mmol), ZnCl2 (0.025 mmol), Et3N (4 mmol) in DMF (3 ml). The vial was sealed with a screw cap and was heated at 338 K with stirring for 16 h. The crude product was purified by
(EtOAc: hexanes = 1:4) followed by recrystallization in EtOAc:hexanes = 1:1 to give the cis ring-opening (III) in 85% yield. X-ray quality crystals were grown from a solution of the title compound in EtOAc:hexanes = 1:1.Hydrogen atoms bonded to C atoms were placed in calculated positions with C—H distances ranging from 0.95–1.00 Å and included in the
in a riding-model approximation with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl). H atoms bonded to O atoms were refined independently with isotropic displacement parameters.Data collection: APEX2 (Bruker, 2012); cell
SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C18H18O2 | F(000) = 2272 |
Mr = 266.32 | Dx = 1.240 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 9819 reflections |
a = 11.4550 (3) Å | θ = 4.3–66.5° |
b = 11.2239 (3) Å | µ = 0.63 mm−1 |
c = 44.3776 (10) Å | T = 150 K |
V = 5705.6 (2) Å3 | Block, colourless |
Z = 16 | 0.20 × 0.20 × 0.19 mm |
Bruker Kappa APEX DUO CCD diffractometer | 4946 independent reflections |
Radiation source: Bruker IµuS | 4644 reflections with I > 2σ(I) |
Multi-layer optics monochromator | Rint = 0.033 |
ϕ and ω scans | θmax = 66.5°, θmin = 4.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −13→13 |
Tmin = 0.707, Tmax = 0.753 | k = −13→13 |
34754 measured reflections | l = −34→52 |
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) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.047P)2 + 2.0379P] where P = (Fo2 + 2Fc2)/3 |
4946 reflections | (Δ/σ)max = 0.001 |
373 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C18H18O2 | V = 5705.6 (2) Å3 |
Mr = 266.32 | Z = 16 |
Orthorhombic, Pbca | Cu Kα radiation |
a = 11.4550 (3) Å | µ = 0.63 mm−1 |
b = 11.2239 (3) Å | T = 150 K |
c = 44.3776 (10) Å | 0.20 × 0.20 × 0.19 mm |
Bruker Kappa APEX DUO CCD diffractometer | 4946 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | 4644 reflections with I > 2σ(I) |
Tmin = 0.707, Tmax = 0.753 | Rint = 0.033 |
34754 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.23 e Å−3 |
4946 reflections | Δρmin = −0.25 e Å−3 |
373 parameters |
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 | ||
O1A | 0.22919 (8) | 0.26848 (9) | 0.120623 (19) | 0.0325 (2) | |
O2A | 0.68544 (7) | 0.53156 (8) | 0.07521 (2) | 0.0302 (2) | |
C1A | 0.20394 (10) | 0.22033 (10) | 0.09162 (3) | 0.0238 (2) | |
H1AA | 0.1625 | 0.1430 | 0.0949 | 0.029* | |
C2A | 0.12087 (10) | 0.30080 (10) | 0.07497 (3) | 0.0236 (2) | |
C3A | 0.04550 (10) | 0.37600 (11) | 0.09018 (3) | 0.0319 (3) | |
H3AA | 0.0512 | 0.3831 | 0.1115 | 0.038* | |
C4A | −0.03824 (12) | 0.44124 (12) | 0.07476 (4) | 0.0453 (4) | |
H4AA | −0.0899 | 0.4922 | 0.0855 | 0.054* | |
C5A | −0.04615 (13) | 0.43192 (14) | 0.04395 (4) | 0.0525 (4) | |
H5AA | −0.1024 | 0.4777 | 0.0333 | 0.063* | |
C6A | 0.02753 (13) | 0.35617 (14) | 0.02840 (3) | 0.0458 (4) | |
H6AA | 0.0207 | 0.3499 | 0.0071 | 0.055* | |
C7A | 0.11210 (11) | 0.28850 (12) | 0.04346 (3) | 0.0301 (3) | |
C8A | 0.18971 (12) | 0.20407 (13) | 0.02778 (3) | 0.0375 (3) | |
C9A | 0.28302 (12) | 0.16040 (12) | 0.04187 (3) | 0.0366 (3) | |
H9AA | 0.3316 | 0.1063 | 0.0312 | 0.044* | |
C10A | 0.31604 (10) | 0.19198 (11) | 0.07382 (3) | 0.0279 (3) | |
H10A | 0.3507 | 0.1188 | 0.0830 | 0.034* | |
C11A | 0.40984 (10) | 0.28772 (10) | 0.07467 (3) | 0.0248 (3) | |
C12A | 0.51443 (10) | 0.26726 (11) | 0.08995 (3) | 0.0270 (3) | |
H12A | 0.5242 | 0.1945 | 0.1006 | 0.032* | |
C13A | 0.60418 (10) | 0.34949 (11) | 0.09013 (3) | 0.0268 (3) | |
H13A | 0.6744 | 0.3331 | 0.1008 | 0.032* | |
C14A | 0.59110 (10) | 0.45625 (10) | 0.07467 (3) | 0.0237 (2) | |
C15A | 0.48724 (10) | 0.48025 (11) | 0.05977 (3) | 0.0256 (3) | |
H15A | 0.4769 | 0.5540 | 0.0496 | 0.031* | |
C16A | 0.39840 (10) | 0.39589 (11) | 0.05975 (3) | 0.0271 (3) | |
H16A | 0.3280 | 0.4127 | 0.0493 | 0.033* | |
C17A | 0.15995 (16) | 0.1685 (2) | −0.00402 (3) | 0.0680 (6) | |
H17A | 0.2182 | 0.1117 | −0.0114 | 0.102* | |
H17B | 0.1597 | 0.2394 | −0.0169 | 0.102* | |
H17C | 0.0826 | 0.1313 | −0.0044 | 0.102* | |
C18A | 0.67564 (12) | 0.63997 (12) | 0.05877 (3) | 0.0373 (3) | |
H18A | 0.7487 | 0.6848 | 0.0604 | 0.056* | |
H18B | 0.6114 | 0.6875 | 0.0670 | 0.056* | |
H18C | 0.6600 | 0.6222 | 0.0375 | 0.056* | |
O1B | 0.27739 (10) | 0.01439 (10) | 0.14040 (2) | 0.0434 (3) | |
O2B | −0.16899 (8) | 0.31196 (9) | 0.14391 (2) | 0.0425 (2) | |
C1B | 0.28972 (12) | −0.00485 (12) | 0.17196 (3) | 0.0346 (3) | |
H1BA | 0.3294 | −0.0835 | 0.1746 | 0.042* | |
C2B | 0.36914 (12) | 0.08848 (11) | 0.18513 (3) | 0.0341 (3) | |
C3B | 0.44909 (13) | 0.14936 (14) | 0.16753 (4) | 0.0484 (4) | |
H3BA | 0.4478 | 0.1393 | 0.1463 | 0.058* | |
C4B | 0.53099 (15) | 0.22476 (16) | 0.18035 (6) | 0.0670 (6) | |
H4BA | 0.5853 | 0.2659 | 0.1680 | 0.080* | |
C5B | 0.53336 (16) | 0.23978 (17) | 0.21103 (6) | 0.0697 (6) | |
H5BA | 0.5902 | 0.2903 | 0.2200 | 0.084* | |
C6B | 0.45262 (16) | 0.18112 (15) | 0.22903 (4) | 0.0569 (5) | |
H6BA | 0.4542 | 0.1929 | 0.2502 | 0.068* | |
C7B | 0.36911 (12) | 0.10518 (12) | 0.21653 (3) | 0.0382 (3) | |
C8B | 0.28066 (13) | 0.04384 (15) | 0.23491 (3) | 0.0445 (4) | |
C9B | 0.19059 (14) | −0.00945 (15) | 0.22167 (3) | 0.0457 (4) | |
H9BA | 0.1347 | −0.0477 | 0.2342 | 0.055* | |
C10B | 0.17150 (12) | −0.01309 (12) | 0.18803 (3) | 0.0362 (3) | |
H10B | 0.1385 | −0.0934 | 0.1832 | 0.043* | |
C11B | 0.08270 (11) | 0.07827 (12) | 0.17737 (3) | 0.0306 (3) | |
C12B | 0.01297 (12) | 0.05211 (12) | 0.15228 (3) | 0.0347 (3) | |
H12B | 0.0224 | −0.0221 | 0.1423 | 0.042* | |
C13B | −0.06856 (12) | 0.13136 (12) | 0.14185 (3) | 0.0344 (3) | |
H13B | −0.1144 | 0.1118 | 0.1247 | 0.041* | |
C14B | −0.08461 (10) | 0.24027 (12) | 0.15619 (3) | 0.0317 (3) | |
C15B | −0.01645 (11) | 0.26885 (12) | 0.18096 (3) | 0.0325 (3) | |
H15B | −0.0264 | 0.3431 | 0.1909 | 0.039* | |
C16B | 0.06686 (11) | 0.18773 (12) | 0.19112 (3) | 0.0314 (3) | |
H16B | 0.1141 | 0.2082 | 0.2079 | 0.038* | |
C17B | 0.29053 (18) | 0.0501 (2) | 0.26884 (4) | 0.0735 (6) | |
H17D | 0.2271 | 0.0040 | 0.2780 | 0.110* | |
H17E | 0.2851 | 0.1333 | 0.2754 | 0.110* | |
H17F | 0.3658 | 0.0169 | 0.2752 | 0.110* | |
C18B | −0.18281 (18) | 0.42644 (19) | 0.15585 (5) | 0.0792 (7) | |
H18D | −0.2433 | 0.4690 | 0.1445 | 0.119* | |
H18E | −0.1089 | 0.4699 | 0.1543 | 0.119* | |
H18F | −0.2059 | 0.4207 | 0.1771 | 0.119* | |
H1O | 0.241 (2) | 0.207 (2) | 0.1329 (5) | 0.077 (7)* | |
H2O | 0.266 (2) | −0.055 (2) | 0.1314 (5) | 0.079 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0338 (5) | 0.0414 (5) | 0.0223 (4) | −0.0019 (4) | −0.0033 (4) | 0.0013 (4) |
O2A | 0.0198 (4) | 0.0288 (5) | 0.0419 (5) | −0.0024 (3) | −0.0011 (3) | −0.0038 (4) |
C1A | 0.0234 (6) | 0.0240 (6) | 0.0240 (6) | −0.0021 (5) | 0.0002 (4) | −0.0002 (5) |
C2A | 0.0202 (5) | 0.0229 (6) | 0.0277 (6) | −0.0057 (5) | −0.0013 (4) | 0.0005 (5) |
C3A | 0.0221 (6) | 0.0278 (6) | 0.0458 (7) | −0.0033 (5) | −0.0023 (5) | −0.0082 (6) |
C4A | 0.0243 (7) | 0.0265 (7) | 0.0851 (12) | −0.0006 (5) | −0.0112 (7) | −0.0047 (7) |
C5A | 0.0326 (7) | 0.0362 (8) | 0.0887 (13) | −0.0068 (6) | −0.0261 (8) | 0.0224 (8) |
C6A | 0.0402 (8) | 0.0541 (9) | 0.0432 (8) | −0.0220 (7) | −0.0191 (6) | 0.0214 (7) |
C7A | 0.0275 (6) | 0.0350 (7) | 0.0278 (6) | −0.0148 (5) | −0.0039 (5) | 0.0052 (5) |
C8A | 0.0348 (7) | 0.0507 (8) | 0.0270 (6) | −0.0223 (6) | 0.0088 (5) | −0.0091 (6) |
C9A | 0.0335 (7) | 0.0334 (7) | 0.0430 (7) | −0.0125 (6) | 0.0161 (6) | −0.0170 (6) |
C10A | 0.0240 (6) | 0.0208 (6) | 0.0390 (7) | 0.0008 (5) | 0.0038 (5) | −0.0009 (5) |
C11A | 0.0215 (6) | 0.0239 (6) | 0.0289 (6) | 0.0020 (5) | 0.0038 (4) | −0.0036 (5) |
C12A | 0.0275 (6) | 0.0249 (6) | 0.0287 (6) | 0.0051 (5) | 0.0012 (5) | 0.0008 (5) |
C13A | 0.0220 (6) | 0.0303 (6) | 0.0280 (6) | 0.0052 (5) | −0.0031 (5) | −0.0042 (5) |
C14A | 0.0184 (5) | 0.0260 (6) | 0.0268 (6) | 0.0004 (4) | 0.0031 (4) | −0.0075 (5) |
C15A | 0.0221 (6) | 0.0227 (6) | 0.0321 (6) | 0.0026 (5) | 0.0002 (5) | −0.0001 (5) |
C16A | 0.0190 (5) | 0.0274 (6) | 0.0350 (6) | 0.0023 (5) | −0.0026 (5) | −0.0006 (5) |
C17A | 0.0593 (10) | 0.1120 (16) | 0.0326 (8) | −0.0406 (11) | 0.0099 (7) | −0.0248 (9) |
C18A | 0.0305 (7) | 0.0323 (7) | 0.0492 (8) | −0.0085 (5) | −0.0003 (6) | 0.0011 (6) |
O1B | 0.0589 (7) | 0.0453 (6) | 0.0261 (5) | 0.0162 (5) | 0.0019 (4) | −0.0020 (4) |
O2B | 0.0304 (5) | 0.0483 (6) | 0.0487 (6) | 0.0054 (4) | −0.0065 (4) | −0.0057 (5) |
C1B | 0.0446 (8) | 0.0313 (7) | 0.0281 (6) | 0.0090 (6) | −0.0011 (6) | 0.0035 (5) |
C2B | 0.0326 (7) | 0.0308 (7) | 0.0389 (7) | 0.0092 (5) | −0.0014 (5) | 0.0077 (6) |
C3B | 0.0366 (8) | 0.0499 (9) | 0.0588 (9) | 0.0091 (7) | 0.0044 (7) | 0.0215 (7) |
C4B | 0.0375 (9) | 0.0526 (10) | 0.1108 (17) | −0.0023 (8) | −0.0066 (10) | 0.0348 (11) |
C5B | 0.0470 (10) | 0.0444 (10) | 0.1175 (18) | −0.0057 (8) | −0.0304 (11) | 0.0114 (11) |
C6B | 0.0571 (10) | 0.0474 (9) | 0.0662 (11) | 0.0103 (8) | −0.0288 (9) | −0.0056 (8) |
C7B | 0.0391 (7) | 0.0367 (7) | 0.0387 (7) | 0.0095 (6) | −0.0099 (6) | 0.0029 (6) |
C8B | 0.0475 (9) | 0.0569 (9) | 0.0290 (7) | 0.0110 (7) | −0.0045 (6) | 0.0084 (6) |
C9B | 0.0472 (8) | 0.0562 (9) | 0.0338 (7) | 0.0015 (7) | 0.0033 (6) | 0.0201 (7) |
C10B | 0.0424 (8) | 0.0319 (7) | 0.0344 (7) | −0.0059 (6) | −0.0031 (6) | 0.0070 (5) |
C11B | 0.0312 (6) | 0.0344 (7) | 0.0262 (6) | −0.0083 (5) | 0.0017 (5) | 0.0045 (5) |
C12B | 0.0392 (7) | 0.0321 (7) | 0.0328 (7) | −0.0080 (6) | −0.0024 (5) | −0.0022 (5) |
C13B | 0.0327 (7) | 0.0401 (7) | 0.0304 (6) | −0.0090 (6) | −0.0049 (5) | −0.0018 (6) |
C14B | 0.0225 (6) | 0.0420 (7) | 0.0306 (6) | −0.0049 (5) | 0.0022 (5) | 0.0015 (5) |
C15B | 0.0289 (6) | 0.0392 (7) | 0.0294 (6) | −0.0041 (5) | 0.0050 (5) | −0.0061 (5) |
C16B | 0.0298 (6) | 0.0426 (7) | 0.0219 (6) | −0.0080 (6) | 0.0009 (5) | −0.0017 (5) |
C17B | 0.0721 (12) | 0.1183 (18) | 0.0302 (8) | 0.0216 (12) | −0.0096 (8) | 0.0101 (10) |
C18B | 0.0637 (12) | 0.0739 (13) | 0.1000 (16) | 0.0367 (11) | −0.0359 (11) | −0.0413 (12) |
O1A—C1A | 1.4256 (14) | O1B—C1B | 1.4239 (16) |
O1A—H1O | 0.89 (2) | O1B—H2O | 0.88 (2) |
O2A—C14A | 1.3722 (14) | O2B—C14B | 1.3705 (16) |
O2A—C18A | 1.4231 (16) | O2B—C18B | 1.399 (2) |
C1A—C2A | 1.5059 (16) | C1B—C2B | 1.506 (2) |
C1A—C10A | 1.5408 (16) | C1B—C10B | 1.5333 (19) |
C1A—H1AA | 1.0000 | C1B—H1BA | 1.0000 |
C2A—C3A | 1.3834 (17) | C2B—C3B | 1.384 (2) |
C2A—C7A | 1.4087 (17) | C2B—C7B | 1.406 (2) |
C3A—C4A | 1.387 (2) | C3B—C4B | 1.386 (3) |
C3A—H3AA | 0.9500 | C3B—H3BA | 0.9500 |
C4A—C5A | 1.374 (3) | C4B—C5B | 1.372 (3) |
C4A—H4AA | 0.9500 | C4B—H4BA | 0.9500 |
C5A—C6A | 1.383 (3) | C5B—C6B | 1.388 (3) |
C5A—H5AA | 0.9500 | C5B—H5BA | 0.9500 |
C6A—C7A | 1.401 (2) | C6B—C7B | 1.396 (2) |
C6A—H6AA | 0.9500 | C6B—H6BA | 0.9500 |
C7A—C8A | 1.474 (2) | C7B—C8B | 1.472 (2) |
C8A—C9A | 1.332 (2) | C8B—C9B | 1.329 (2) |
C8A—C17A | 1.5060 (19) | C8B—C17B | 1.512 (2) |
C9A—C10A | 1.5095 (19) | C9B—C10B | 1.5095 (19) |
C9A—H9AA | 0.9500 | C9B—H9BA | 0.9500 |
C10A—C11A | 1.5201 (16) | C10B—C11B | 1.5197 (19) |
C10A—H10A | 1.0000 | C10B—H10B | 1.0000 |
C11A—C16A | 1.3891 (17) | C11B—C16B | 1.3837 (19) |
C11A—C12A | 1.3956 (17) | C11B—C12B | 1.4015 (18) |
C12A—C13A | 1.3817 (17) | C12B—C13B | 1.370 (2) |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C13A—C14A | 1.3889 (17) | C13B—C14B | 1.390 (2) |
C13A—H13A | 0.9500 | C13B—H13B | 0.9500 |
C14A—C15A | 1.3877 (16) | C14B—C15B | 1.3862 (18) |
C15A—C16A | 1.3900 (17) | C15B—C16B | 1.3939 (19) |
C15A—H15A | 0.9500 | C15B—H15B | 0.9500 |
C16A—H16A | 0.9500 | C16B—H16B | 0.9500 |
C17A—H17A | 0.9800 | C17B—H17D | 0.9800 |
C17A—H17B | 0.9800 | C17B—H17E | 0.9800 |
C17A—H17C | 0.9800 | C17B—H17F | 0.9800 |
C18A—H18A | 0.9800 | C18B—H18D | 0.9800 |
C18A—H18B | 0.9800 | C18B—H18E | 0.9800 |
C18A—H18C | 0.9800 | C18B—H18F | 0.9800 |
C1A—O1A—H1O | 107.1 (14) | C1B—O1B—H2O | 108.9 (15) |
C14A—O2A—C18A | 117.10 (9) | C14B—O2B—C18B | 117.94 (12) |
O1A—C1A—C2A | 110.12 (9) | O1B—C1B—C2B | 109.66 (11) |
O1A—C1A—C10A | 111.84 (9) | O1B—C1B—C10B | 112.26 (11) |
C2A—C1A—C10A | 113.51 (10) | C2B—C1B—C10B | 113.26 (11) |
O1A—C1A—H1AA | 107.0 | O1B—C1B—H1BA | 107.1 |
C2A—C1A—H1AA | 107.0 | C2B—C1B—H1BA | 107.1 |
C10A—C1A—H1AA | 107.0 | C10B—C1B—H1BA | 107.1 |
C3A—C2A—C7A | 119.99 (11) | C3B—C2B—C7B | 119.58 (14) |
C3A—C2A—C1A | 121.38 (11) | C3B—C2B—C1B | 121.61 (13) |
C7A—C2A—C1A | 118.26 (11) | C7B—C2B—C1B | 118.52 (12) |
C2A—C3A—C4A | 120.85 (13) | C2B—C3B—C4B | 121.18 (17) |
C2A—C3A—H3AA | 119.6 | C2B—C3B—H3BA | 119.4 |
C4A—C3A—H3AA | 119.6 | C4B—C3B—H3BA | 119.4 |
C5A—C4A—C3A | 119.74 (14) | C5B—C4B—C3B | 119.73 (17) |
C5A—C4A—H4AA | 120.1 | C5B—C4B—H4BA | 120.1 |
C3A—C4A—H4AA | 120.1 | C3B—C4B—H4BA | 120.1 |
C4A—C5A—C6A | 120.21 (13) | C4B—C5B—C6B | 119.96 (17) |
C4A—C5A—H5AA | 119.9 | C4B—C5B—H5BA | 120.0 |
C6A—C5A—H5AA | 119.9 | C6B—C5B—H5BA | 120.0 |
C5A—C6A—C7A | 121.17 (14) | C5B—C6B—C7B | 121.18 (18) |
C5A—C6A—H6AA | 119.4 | C5B—C6B—H6BA | 119.4 |
C7A—C6A—H6AA | 119.4 | C7B—C6B—H6BA | 119.4 |
C6A—C7A—C2A | 118.01 (13) | C6B—C7B—C2B | 118.35 (15) |
C6A—C7A—C8A | 122.73 (13) | C6B—C7B—C8B | 122.50 (14) |
C2A—C7A—C8A | 119.24 (11) | C2B—C7B—C8B | 119.14 (13) |
C9A—C8A—C7A | 119.95 (11) | C9B—C8B—C7B | 120.00 (12) |
C9A—C8A—C17A | 121.61 (15) | C9B—C8B—C17B | 121.27 (16) |
C7A—C8A—C17A | 118.44 (14) | C7B—C8B—C17B | 118.60 (15) |
C8A—C9A—C10A | 123.75 (12) | C8B—C9B—C10B | 124.18 (13) |
C8A—C9A—H9AA | 118.1 | C8B—C9B—H9BA | 117.9 |
C10A—C9A—H9AA | 118.1 | C10B—C9B—H9BA | 117.9 |
C9A—C10A—C11A | 111.50 (10) | C9B—C10B—C11B | 112.73 (12) |
C9A—C10A—C1A | 108.73 (10) | C9B—C10B—C1B | 109.29 (11) |
C11A—C10A—C1A | 115.49 (10) | C11B—C10B—C1B | 113.94 (10) |
C9A—C10A—H10A | 106.9 | C9B—C10B—H10B | 106.8 |
C11A—C10A—H10A | 106.9 | C11B—C10B—H10B | 106.8 |
C1A—C10A—H10A | 106.9 | C1B—C10B—H10B | 106.8 |
C16A—C11A—C12A | 117.15 (11) | C16B—C11B—C12B | 117.49 (12) |
C16A—C11A—C10A | 122.64 (11) | C16B—C11B—C10B | 123.35 (11) |
C12A—C11A—C10A | 120.17 (11) | C12B—C11B—C10B | 119.16 (12) |
C13A—C12A—C11A | 122.11 (11) | C13B—C12B—C11B | 121.39 (13) |
C13A—C12A—H12A | 118.9 | C13B—C12B—H12B | 119.3 |
C11A—C12A—H12A | 118.9 | C11B—C12B—H12B | 119.3 |
C12A—C13A—C14A | 119.55 (11) | C12B—C13B—C14B | 120.41 (12) |
C12A—C13A—H13A | 120.2 | C12B—C13B—H13B | 119.8 |
C14A—C13A—H13A | 120.2 | C14B—C13B—H13B | 119.8 |
O2A—C14A—C15A | 124.33 (11) | O2B—C14B—C15B | 125.22 (12) |
O2A—C14A—C13A | 115.97 (10) | O2B—C14B—C13B | 115.31 (11) |
C15A—C14A—C13A | 119.70 (11) | C15B—C14B—C13B | 119.47 (12) |
C14A—C15A—C16A | 119.71 (11) | C14B—C15B—C16B | 119.41 (12) |
C14A—C15A—H15A | 120.1 | C14B—C15B—H15B | 120.3 |
C16A—C15A—H15A | 120.1 | C16B—C15B—H15B | 120.3 |
C11A—C16A—C15A | 121.74 (11) | C11B—C16B—C15B | 121.81 (12) |
C11A—C16A—H16A | 119.1 | C11B—C16B—H16B | 119.1 |
C15A—C16A—H16A | 119.1 | C15B—C16B—H16B | 119.1 |
C8A—C17A—H17A | 109.5 | C8B—C17B—H17D | 109.5 |
C8A—C17A—H17B | 109.5 | C8B—C17B—H17E | 109.5 |
H17A—C17A—H17B | 109.5 | H17D—C17B—H17E | 109.5 |
C8A—C17A—H17C | 109.5 | C8B—C17B—H17F | 109.5 |
H17A—C17A—H17C | 109.5 | H17D—C17B—H17F | 109.5 |
H17B—C17A—H17C | 109.5 | H17E—C17B—H17F | 109.5 |
O2A—C18A—H18A | 109.5 | O2B—C18B—H18D | 109.5 |
O2A—C18A—H18B | 109.5 | O2B—C18B—H18E | 109.5 |
H18A—C18A—H18B | 109.5 | H18D—C18B—H18E | 109.5 |
O2A—C18A—H18C | 109.5 | O2B—C18B—H18F | 109.5 |
H18A—C18A—H18C | 109.5 | H18D—C18B—H18F | 109.5 |
H18B—C18A—H18C | 109.5 | H18E—C18B—H18F | 109.5 |
O1A—C1A—C2A—C3A | −25.34 (14) | O1B—C1B—C2B—C3B | −22.59 (17) |
C10A—C1A—C2A—C3A | −151.59 (11) | C10B—C1B—C2B—C3B | −148.85 (12) |
O1A—C1A—C2A—C7A | 161.64 (10) | O1B—C1B—C2B—C7B | 163.61 (11) |
C10A—C1A—C2A—C7A | 35.38 (14) | C10B—C1B—C2B—C7B | 37.35 (16) |
C7A—C2A—C3A—C4A | −0.87 (18) | C7B—C2B—C3B—C4B | 1.4 (2) |
C1A—C2A—C3A—C4A | −173.78 (11) | C1B—C2B—C3B—C4B | −172.34 (14) |
C2A—C3A—C4A—C5A | −0.5 (2) | C2B—C3B—C4B—C5B | 0.0 (2) |
C3A—C4A—C5A—C6A | 1.2 (2) | C3B—C4B—C5B—C6B | −1.1 (3) |
C4A—C5A—C6A—C7A | −0.6 (2) | C4B—C5B—C6B—C7B | 0.8 (3) |
C5A—C6A—C7A—C2A | −0.68 (19) | C5B—C6B—C7B—C2B | 0.5 (2) |
C5A—C6A—C7A—C8A | 178.05 (12) | C5B—C6B—C7B—C8B | −178.57 (15) |
C3A—C2A—C7A—C6A | 1.42 (17) | C3B—C2B—C7B—C6B | −1.6 (2) |
C1A—C2A—C7A—C6A | 174.54 (11) | C1B—C2B—C7B—C6B | 172.31 (12) |
C3A—C2A—C7A—C8A | −177.36 (11) | C3B—C2B—C7B—C8B | 177.51 (13) |
C1A—C2A—C7A—C8A | −4.23 (16) | C1B—C2B—C7B—C8B | −8.56 (18) |
C6A—C7A—C8A—C9A | 166.49 (12) | C6B—C7B—C8B—C9B | 167.58 (15) |
C2A—C7A—C8A—C9A | −14.79 (18) | C2B—C7B—C8B—C9B | −11.5 (2) |
C6A—C7A—C8A—C17A | −14.08 (19) | C6B—C7B—C8B—C17B | −8.4 (2) |
C2A—C7A—C8A—C17A | 164.64 (13) | C2B—C7B—C8B—C17B | 172.50 (15) |
C7A—C8A—C9A—C10A | 0.12 (19) | C7B—C8B—C9B—C10B | 0.5 (2) |
C17A—C8A—C9A—C10A | −179.30 (13) | C17B—C8B—C9B—C10B | 176.41 (16) |
C8A—C9A—C10A—C11A | −98.56 (14) | C8B—C9B—C10B—C11B | −100.29 (17) |
C8A—C9A—C10A—C1A | 29.90 (17) | C8B—C9B—C10B—C1B | 27.5 (2) |
O1A—C1A—C10A—C9A | −171.04 (10) | O1B—C1B—C10B—C9B | −169.13 (12) |
C2A—C1A—C10A—C9A | −45.70 (13) | C2B—C1B—C10B—C9B | −44.26 (15) |
O1A—C1A—C10A—C11A | −44.85 (14) | O1B—C1B—C10B—C11B | −42.02 (16) |
C2A—C1A—C10A—C11A | 80.49 (13) | C2B—C1B—C10B—C11B | 82.85 (14) |
C9A—C10A—C11A—C16A | 53.71 (15) | C9B—C10B—C11B—C16B | 31.98 (17) |
C1A—C10A—C11A—C16A | −71.05 (15) | C1B—C10B—C11B—C16B | −93.32 (15) |
C9A—C10A—C11A—C12A | −123.89 (12) | C9B—C10B—C11B—C12B | −148.38 (13) |
C1A—C10A—C11A—C12A | 111.34 (12) | C1B—C10B—C11B—C12B | 86.32 (15) |
C16A—C11A—C12A—C13A | −0.81 (17) | C16B—C11B—C12B—C13B | −0.52 (19) |
C10A—C11A—C12A—C13A | 176.92 (11) | C10B—C11B—C12B—C13B | 179.82 (12) |
C11A—C12A—C13A—C14A | −0.07 (18) | C11B—C12B—C13B—C14B | −0.4 (2) |
C18A—O2A—C14A—C15A | −1.38 (16) | C18B—O2B—C14B—C15B | 4.6 (2) |
C18A—O2A—C14A—C13A | 178.12 (11) | C18B—O2B—C14B—C13B | −175.02 (16) |
C12A—C13A—C14A—O2A | −178.15 (10) | C12B—C13B—C14B—O2B | −179.59 (12) |
C12A—C13A—C14A—C15A | 1.37 (17) | C12B—C13B—C14B—C15B | 0.76 (19) |
O2A—C14A—C15A—C16A | 177.74 (11) | O2B—C14B—C15B—C16B | −179.77 (11) |
C13A—C14A—C15A—C16A | −1.75 (17) | C13B—C14B—C15B—C16B | −0.15 (18) |
C12A—C11A—C16A—C15A | 0.42 (17) | C12B—C11B—C16B—C15B | 1.14 (18) |
C10A—C11A—C16A—C15A | −177.25 (11) | C10B—C11B—C16B—C15B | −179.21 (12) |
C14A—C15A—C16A—C11A | 0.85 (18) | C14B—C15B—C16B—C11B | −0.82 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1O···O1B | 0.89 (2) | 2.23 (2) | 3.0346 (15) | 150.6 (19) |
O1B—H2O···O1Ai | 0.88 (2) | 2.04 (2) | 2.8973 (15) | 163 (2) |
Symmetry code: (i) −x+1/2, y−1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1O···O1B | 0.89 (2) | 2.23 (2) | 3.0346 (15) | 150.6 (19) |
O1B—H2O···O1Ai | 0.88 (2) | 2.04 (2) | 2.8973 (15) | 163 (2) |
Symmetry code: (i) −x+1/2, y−1/2, z. |
Acknowledgements
This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC).
References
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We have recently investigated the metal-catalyzed ring-opening reactions of oxanorbornadiene compounds (Jack et al., 2013). When expanding this reaction using a palladium catalyst, C1-methyl substituted oxanorbornadiene (I) (see Fig. 1) reacts with 4-methoxy-1-iodobenzene (II) in the presence of PdCl2(PPh3)2, Zn, ZnCl2, Et3N in DMF, to give the ring-opening product (III) as a single regio- and stereoisomer. The stereochemistry and regiochemistry of the product was determined by this single-crystal X-ray analysis. Although different regio- and stereoisomers could be formed, the only ring-opening product obtained was found to have a cis stereochemistry.
There are two independent molecules [A and B] in the asymmetric unit which are shown in Fig. 2. The dihedral angles between the two benzene rings [C2–C7/C11–C16] are 88.31 (4) and 86.27 (4)°, for moleclues A and B respetively. The cyclohexene rings [C1/C2/C7—C10] are in half-chair conformations. In the crystal, O—H···O hydrogen bonds link alternating types of molecules into chains along [010] with graph-set C22(4) (Bernstein et al., 1995) (see Fig. 3).