Facile and Stereospecific Synthesis of Diverse β-N-Glycosyl Sulfonamide Scaffolds via Palladium Catalysis
Zhong, Lei; Wang, Qunliang; Wang, Yujuan; Cheng, Yiyang; Xiong, Yimeng; Peng, Haibo; Zhou, Zhen; He, Yun; Dai, Yuanwei; Chemical Communications  (2023) –; doi:10.1039/D3CC04063A

data_7132174
_publ_section_title
;
 Facile and Stereospecific Synthesis of Diverse \b-N-Glycosyl Sulfonamide
 Scaffolds via Palladium Catalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04063A
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H41 N O5 S Si'
_chemical_formula_sum            'C30 H41 N O5 S Si'
_chemical_formula_weight         555.79
_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
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2fp6q2
_audit_creation_date             2022-07-05
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2023-04-07 deposited with the CCDC.	2023-10-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5387(3)
_cell_length_b                   13.4947(6)
_cell_length_c                   30.0141(12)
_cell_measurement_reflns_used    4201
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0020
_cell_measurement_theta_min      1.6750
_cell_volume                     3053.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -34.00  37.00   1.00   10.23    --   18.74 -38.00 120.00   71
  2  \w     -7.00  85.00   1.00   10.23    --   18.74  19.00 -30.00   92
  3  \w    -41.00 -14.00   1.00   10.23    --  -18.93 -77.00  60.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0552779000
_diffrn_orient_matrix_UB_12      0.0136951000
_diffrn_orient_matrix_UB_13      -0.0181203000
_diffrn_orient_matrix_UB_21      -0.0549140000
_diffrn_orient_matrix_UB_22      0.0415756000
_diffrn_orient_matrix_UB_23      -0.0042754000
_diffrn_orient_matrix_UB_31      0.0526750000
_diffrn_orient_matrix_UB_32      0.0290647000
_diffrn_orient_matrix_UB_33      0.0145898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            11984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.160
_diffrn_reflns_theta_min         1.655
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       block
_exptl_crystal_F_000             1192
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1531 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         6909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0515
_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^+0.2066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1242
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.786
_reflns_number_gt                4949
_reflns_number_total             6909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04063a2.cif
_cod_data_source_block           20220705-wql-1
_cod_database_code               7132174
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H41 N O5 S Si'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00D(H00D), C00F(H00F), C00J(H00J), C00N(H00N), C00P(H00P)
2.b Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00G(H00G), C00K(H00K), C00L(H00L), C00O(H00O), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V)
2.d Idealised Me refined as rotating group:
 C00W(H00E,H00H,H00I), C00X(H00M,H00W,H00X), C00Y(H00Y,H,HA), C00Z(H00Z,HB,HC),
  C010(H01A,H01B,H01C), C011(H01D,H01E,H01F), C012(H01G,H01H,H01I)
2.e Idealised tetrahedral OH refined as rotating group:
 O008(H008)
;
_shelx_res_checksum              47693
_shelx_hkl_checksum              76876
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.672