Convergent Total Synthesis of Hikizimycin Enabled by Intermolecular Radical Addition to Aldehyde.
Fujino, Haruka; Fukuda, Takumi; Nagatomo, Masanori; Inoue, Masayuki; Journal of the American Chemical Society 142 (2020) 13227–13234; doi:10.1021/jacs.0c06354

data_4135116
_publ_section_title
;
 Convergent Total Synthesis of Hikizimycin Enabled by Intermolecular
 Radical Addition to Aldehyde.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13227
_journal_page_last               13234
_journal_paper_doi               10.1021/jacs.0c06354
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C56 H58 O18'
_chemical_formula_sum            'C56 H58 O18'
_chemical_formula_weight         1019.06
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.803(11)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   10.626(11)
_cell_length_b                   19.78(2)
_cell_length_c                   12.823(14)
_cell_measurement_reflns_used    8088
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.10
_cell_volume                     2656(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19334
_diffrn_reflns_point_group_measured_fraction_full 0.774
_diffrn_reflns_point_group_measured_fraction_max 0.740
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.416
_diffrn_reflns_theta_min         3.092
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1076.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.29
_refine_ls_abs_structure_details
;
 Flack x determined using 1514 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       0.0047(8)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     675
_refine_ls_number_reflns         8965
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0764
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0369P)^2^+3.4091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1639
_reflns_Friedel_coverage         0.466
_reflns_Friedel_fraction_full    0.541
_reflns_Friedel_fraction_max     0.484
_reflns_number_gt                7354
_reflns_number_total             8965
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja0c06354_si_002.cif
_cod_data_source_block           HAF-14-117-minor-Mo-5
_cod_depositor_comments
;Adding full bibliography for 4135116.cif.

 Adding full bibliography for 4135116.cif.
;
_cod_database_code               4135116
_shelx_res_checksum              44941
_shelx_hkl_checksum              80674