First Experimental and Theoretical Evidence of a Deactivating Enone Dienophile in the Transannular Diels-Alder Reaction
Élyse Bourque; Pierre Deslongchamps; Yves L. Dory; Journal of Organic Chemistry 68 (2003) 2390–2397; doi:10.1021/jo0265129

data_4022311
_publ_section_title
;
 First Experimental and Theoretical Evidence of a Deactivating
 Enone Dienophile in the Transannular Diels-Alder Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2390
_journal_page_last               2397
_journal_paper_doi               10.1021/jo0265129
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         'C29 H44 O9'
_chemical_formula_sum            'C29 H44 O9'
_chemical_formula_weight         536.64
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 113.728(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.676(5)
_cell_length_b                   16.9509(16)
_cell_length_c                   13.899(3)
_cell_measurement_temperature    293(2)
_cell_volume                     2949.6(12)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5715
_diffrn_reflns_theta_full        70.18
_diffrn_reflns_theta_max         70.18
_diffrn_reflns_theta_min         3.83
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       prism
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         5484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0628
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0861P)^2^+0.3316P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1903
_reflns_number_gt                3411
_reflns_number_total             5484
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0265129si20030204_031629_3.cif
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022311