Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by a Bis-thiourea.
Li, Qiuhan; Levi, Samuel; Jacobsen, Eric N.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c04255

data_4135092
_publ_section_title
;
 Highly Selective \b-Mannosylations and \b-Rhamnosylations Catalyzed by a
 Bis-thiourea.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c04255
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C31 H48.67 N O10.33'
_chemical_formula_weight         600.73
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.905(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.1612(3)
_cell_length_b                   30.938(2)
_cell_length_c                   9.7231(6)
_cell_measurement_reflns_used    9260
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.7
_cell_measurement_theta_min      4.37
_cell_volume                     1551.70(17)
_computing_cell_refinement       'SAINT 8.37A (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 8.37A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            41074
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        66.988
_diffrn_reflns_theta_max         66.988
_diffrn_reflns_theta_min         2.856
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  0.8058
_exptl_absorpt_correction_T_min  0.7569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             649
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 2517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(5)
_refine_ls_extinction_coef       0.0050(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     450
_refine_ls_number_reflns         5409
_refine_ls_number_restraints     80
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0332
_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^)+(0.0479P)^2^+0.5525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0904
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                5349
_reflns_number_total             5409
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c04255_si_002.cif
_cod_data_source_block           QL-III-Tyr
_cod_original_cell_volume        1551.72(17)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4135092
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.871
_shelx_estimated_absorpt_t_max   0.925
_refine_ls_abs_structure_hooft   -0.04(4)
_shelx_res_checksum              53239
_shelx_hkl_checksum              65104