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_4038595
_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 H41 N O5 S'
_chemical_formula_sum            'C42 H41 N O5 S'
_chemical_formula_weight         671.82
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 100.021(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.9289(4)
_cell_length_b                   8.8193(3)
_cell_length_c                   16.9246(6)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.57
_cell_measurement_theta_min      4.97
_cell_volume                     1753.38(10)
_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  'APEX3 v2018.7--RC8 (Bruker AXS, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25115
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.608
_diffrn_reflns_theta_min         2.651
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    1.194
_exptl_absorpt_correction_T_max  0.8645
_exptl_absorpt_correction_T_min  0.7030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
; 
 Flack x determined using 2768 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.011(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         7005
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0291P)^2^+0.6554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0896
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                6514
_reflns_number_total             7005
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00943_si_002.cif
_cod_data_source_block           d15819
_cod_original_cell_volume        1753.38(11)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038595
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.798
_shelx_estimated_absorpt_t_max   0.963
_shelx_res_checksum              4196
_shelx_hkl_checksum              41287