Site-Selective and Stereoselective C-H Alkylations of Carbohydrates via Combined Diarylborinic Acid and Photoredox Catalysis.
Dimakos, Victoria; Su, Hsin Y.; Garrett, Graham E.; Taylor, Mark S.; Journal of the American Chemical Society 141 (2019) 5149–5153; doi:10.1021/jacs.9b01531

data_4128384
_publ_section_title
;
 Site-Selective and Stereoselective C-H Alkylations of Carbohydrates via
 Combined Diarylborinic Acid and Photoredox Catalysis.
;
_journal_issue                   13
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5149
_journal_page_last               5153
_journal_paper_doi               10.1021/jacs.9b01531
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H38 O7 S Si'
_chemical_formula_sum            'C25 H38 O7 S Si'
_chemical_formula_weight         510.70
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   18.6122(4)
_cell_length_b                   22.6992(4)
_cell_length_c                   27.1140(5)
_cell_measurement_reflns_used    9753
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      60.78
_cell_measurement_theta_min      2.54
_cell_volume                     11455.2(4)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            255409
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.652
_diffrn_reflns_theta_max         67.652
_diffrn_reflns_theta_min         2.880
_diffrn_source                   'Bruker ImuS with multi-layer optics'
_exptl_absorpt_coefficient_mu    1.724
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_description       needle
_exptl_crystal_F_000             4384
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.991
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
; 
 Flack x determined using 7133 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.023(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1320
_refine_ls_number_reflns         20399
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1261P)^2^+6.6254P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.1990
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                17528
_reflns_number_total             20399
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b01531_si_002.cif
_cod_data_source_block           d1862
_cod_database_code               4128384
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.560
_shelx_estimated_absorpt_t_max   0.874
_shelx_res_checksum              61891
_shelx_hkl_checksum              48299