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_4024102
_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            'C16 H20 O4'
_chemical_formula_weight         276.32
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.521(2)
_cell_length_b                   9.1760(10)
_cell_length_c                   17.747(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1387.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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    0.0089
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2180
_diffrn_reflns_theta_full        64.94
_diffrn_reflns_theta_max         64.94
_diffrn_reflns_theta_min         4.98
_exptl_absorpt_coefficient_mu    0.769
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       0.097(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   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.211
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0712P)^2^+0.3472P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                2156
_reflns_number_total             2180
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0708893si20070430_022656.cif
_cod_data_source_block           jgd52
_cod_database_code               4024102