A Total Synthesis of Bifidenone.
Huang, Zhongping; Williams, Russell B.; O'Neil-Johnson, Mark; Eldridge, Gary R.; Mangette, John E.; Starks, Courtney M.; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b00202

data_4032672
_publ_section_title
;
 A Total Synthesis of Bifidenone.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b00202
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H32 O8'
_chemical_formula_sum            'C27 H32 O8'
_chemical_formula_weight         484.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 95.4120(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.5637(5)
_cell_length_b                   6.4493(3)
_cell_length_c                   13.7872(6)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.33
_cell_measurement_theta_min      3.22
_cell_volume                     1200.68(9)
_computing_cell_refinement       'SAINT V.8.34 (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 v.2014.11-0 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT Ver. 6.22'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37673
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.362
_diffrn_reflns_theta_min         3.273
_diffrn_source                   'INCOATEC ImuS micro-focus source'
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  0.9528
_exptl_absorpt_correction_T_min  0.7925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2014)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 2057 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0239
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.2209P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0629
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                4682
_reflns_number_total             4737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00202_si_002.cif
_cod_data_source_block           sad_a
_cod_database_code               4032672
_shelx_estimated_absorpt_t_min   0.793
_shelx_estimated_absorpt_t_max   0.953
_shelxl_version_number           2014/6
_shelx_res_checksum              17644
_shelx_hkl_checksum              78687