Efficient Access to Orthoquinols and Their [4 + 2] Cyclodimers via SIBX-Mediated Hydroxylative Phenol Dearomatization
Nathalie Lebrasseur; Julien Gagnepain; Aurélie Ozanne-Beaudenon; Jean-Michel Léger; Stéphane Quideau; Journal of Organic Chemistry 72 (2007) 6280–6283; doi:10.1021/jo0708893

data_4024103
_publ_section_title
;
 Efficient Access to Orthoquinols and Their [4 + 2] Cyclodimers
 via SIBX-Mediated Hydroxylative Phenol Dearomatization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6280
_journal_page_last               6283
_journal_paper_doi               10.1021/jo0708893
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C20 H28 O4'
_chemical_formula_weight         332.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.954(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1430(6)
_cell_length_b                   21.7743(13)
_cell_length_c                   8.3134(6)
_cell_measurement_temperature    113(2)
_cell_volume                     1765.3(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3346
_diffrn_reflns_theta_full        72.23
_diffrn_reflns_theta_max         72.23
_diffrn_reflns_theta_min         6.87
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  0.9345
_exptl_absorpt_correction_T_min  0.8748
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       0.0012(5)
_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   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0859
_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^)+(0.0766P)^2^+6.4423P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2378
_refine_ls_wR_factor_ref         0.2414
_reflns_number_gt                2782
_reflns_number_total             3346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0708893si20070430_022725.cif
_cod_data_source_block           jgc2663b
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024103