Manganese(III)-mediated transformations of phloroglucinols: a formal oxidative [4 + 2] cycloaddition leading to bicyclo[2.2.2]octadiones.
Mitasev, Branko; Porco, Jr, John A; Organic letters 11 (2009) 2285–2288; doi:10.1021/ol900590t

data_1503906
_publ_section_title
;
 Manganese(III)-mediated transformations of phloroglucinols: a formal
 oxidative [4 + 2] cycloaddition leading to bicyclo[2.2.2]octadiones.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2285
_journal_page_last               2288
_journal_paper_doi               10.1021/ol900590t
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C28 H30 O4'
_chemical_formula_sum            'C28 H30 O4'
_chemical_formula_weight         430.52
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 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                   24.138(3)
_cell_length_b                   8.8059(8)
_cell_length_c                   10.1770(11)
_cell_measurement_reflns_used    972
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      18.97
_cell_measurement_theta_min      2.62
_cell_volume                     2163.2(4)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7891
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         1662
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                1298
_reflns_number_total             1662
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900590t_si_002.cif
_cod_data_source_block           compound6
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pca2(1)
_cod_database_code               1503906