Indolylthio glycosides as effective building blocks for chemical glycosylation.
Shrestha, Ganesh; Panza, Matteo; Singh, Yashapal; Rath, Nigam P.; Demchenko, Alexei V.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00943

data_4038596
_publ_section_title
;
 Indolylthio glycosides as effective building blocks for chemical
 glycosylation.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00943
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H33 N O9 S'
_chemical_formula_sum            'C42 H33 N O9 S'
_chemical_formula_weight         727.75
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 95.889(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9632(2)
_cell_length_b                   18.9516(9)
_cell_length_c                   15.9602(7)
_cell_measurement_reflns_used    6216
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.82
_cell_measurement_theta_min      2.50
_cell_volume                     1794.18(13)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24279
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_min         2.149
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.9420
_exptl_absorpt_correction_T_min  0.9063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.233
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Flack x determined using 2415 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         8263
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.0907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0852
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6220
_reflns_number_total             8263
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00943_si_001.cif
_cod_data_source_block           d1119-180K
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038596
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.966
_shelx_res_checksum              1144
_shelx_hkl_checksum              10331