Synthesis of Aryl C-Glycosides via Iron-Catalyzed Cross Coupling of Halosugars: Stereoselective Anomeric Arylation of Glycosyl Radicals.
Adak, Laksmikanta; Kawamura, Shintaro; Toma, Gabriel; Takenaka, Toshio; Isozaki, Katsuhiro; Takaya, Hikaru; Orita, Akihiro; Li, Ho C.; Shing, Tony K. M.; Nakamura, Masaharu; Journal of the American Chemical Society 139 (2017) 10693–10701; doi:10.1021/jacs.7b03867

data_4131303
_publ_section_title
;
 Synthesis of Aryl C-Glycosides via Iron-Catalyzed Cross Coupling of
 Halosugars: Stereoselective Anomeric Arylation of Glycosyl Radicals.
;
_journal_issue                   31
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10693
_journal_page_last               10701
_journal_paper_doi               10.1021/jacs.7b03867
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C54 H88 Cl2 Fe P2 Si8'
_chemical_formula_weight         1150.65
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n 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                   34.9141(3)
_cell_length_b                   10.91530(10)
_cell_length_c                   18.66070(10)
_cell_measurement_reflns_used    49370
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.30
_cell_volume                     7111.55(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 28.571
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku Saturn724+'
_diffrn_measurement_method       'Oscillation Photograph'
_diffrn_radiation_monochromator  'Si(111) Channel Cut'
_diffrn_radiation_source         'Synchrotron radiation SPring-8 BL38B1'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.70000
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            47961
_diffrn_reflns_theta_full        27.33
_diffrn_reflns_theta_max         27.33
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    0.436
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.075
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2456
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.021(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     748
_refine_ls_number_reflns         16082
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0372P)^2^+5.5656P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                14942
_reflns_number_total             16082
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja7b03867_si_002.cif
_cod_data_source_block           ydkr
_cod_original_sg_symbol_H-M      Pna21
_cod_database_code               4131303