Hydrogen-Bonding-Assisted Exogenous Nucleophilic Reagent Effect for β-Selective Glycosylation of Rare 3-Amino Sugars.
Zeng, Jing; Wang, Ruobin; Zhang, Shuxin; Fang, Jing; Liu, Shanshan; Sun, Guangfei; Xu, Bingbing; Xiao, Ying; Fu, Dengxian; Zhang, Wenqi; Hu, Yixin; Wan, Qian; Journal of the American Chemical Society 141 (2019) 8509–8515; doi:10.1021/jacs.9b01862

data_4128759
_publ_section_title
;
 Hydrogen-Bonding-Assisted Exogenous Nucleophilic Reagent Effect for
 \b-Selective Glycosylation of Rare 3-Amino Sugars.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8509
_journal_page_last               8515
_journal_paper_doi               10.1021/jacs.9b01862
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H36 N4 O13 S2'
_chemical_formula_sum            'C27 H36 N4 O13 S2'
_chemical_formula_weight         688.72
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.62899(5)
_cell_length_b                   8.62984(4)
_cell_length_c                   47.2575(2)
_cell_measurement_reflns_used    63838
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6230
_cell_measurement_theta_min      3.6750
_cell_volume                     3111.29(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.982
_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     39.00  65.00   0.50    0.50    --    0.00  38.00 150.00   52
  2  \w    -17.00  12.00   0.50    0.50    --    0.00  38.00 150.00   58
  3  \w    -16.00  65.00   0.50    0.50    --    0.00  38.00  90.00  162
  4  \w    -32.00   0.00   0.50    0.50    --    0.00 -82.00-120.00   64
  5  \w    -16.00  33.00   0.50    0.50    --    0.00  38.00-150.00   98
  6  \w     35.00  71.00   0.50    0.50    --    0.00  38.00-120.00   72
  7  \w    -17.00  28.00   0.50    0.50    --    0.00  38.00-120.00   90
  8  \w    -17.00  89.00   0.50    0.50    --    0.00  38.00 -60.00  212
  9  \w    -17.00  71.00   0.50    0.50    --    0.00  38.00  30.00  176
 10  \w     60.00  85.00   0.50    0.50    --    0.00  38.00-150.00   50
 11  \w    157.00 184.00   0.50    0.50    --   94.60  60.00 -71.33   54
 12  \w     66.00  91.00   0.50    0.50    --   94.60  74.00 164.38   50
 13  \w    114.00 157.00   0.50    0.50    --   94.60  74.00 164.38   86
 14  \w     67.00  93.00   0.50    0.50    --   94.60  71.00 178.11   52
 15  \w     70.00 180.00   0.50    0.50    --   94.60  65.00-111.77  220
 16  \w     71.00 102.00   0.50    0.50    --   94.60  60.00 -71.33   62
 17  \w    104.00 130.00   0.50    0.50    --   94.60  72.00 137.16   52
 18  \w     70.00 182.00   0.50    0.50    --   94.60  65.00 127.18  224
 19  \w     66.00  91.00   0.50    0.50    --   94.60  75.00  80.97   50
 20  \w    144.00 175.00   0.50    0.50    --   94.60  68.00 100.83   62
 21  \w     66.00 105.00   0.50    0.50    --   94.60  74.00   6.14   78
 22  \w    114.00 180.00   0.50    0.50    --   94.60  74.00   6.14  132
 23  \w     69.00  96.00   0.50    0.50    --   94.60  66.00  39.78   54
 24  \w     67.00  92.00   0.50    0.50    --   94.60  72.00 -95.95   50
 25  \w     66.00  91.00   0.50    0.50    --   94.60  75.00  67.73   50
 26  \w     66.00  91.00   0.50    0.50    --   94.60  75.00  18.44   50
 27  \w    102.00 184.00   0.50    0.50    --   94.60  75.00  18.44  164
 28  \w     69.00  95.00   0.50    0.50    --   94.60  67.00 -59.27   52
 29  \w     66.00  91.00   0.50    0.50    --   94.60  74.00 -21.79   50
 30  \w    114.00 141.00   0.50    0.50    --   94.60  74.00 -21.79   54
 31  \w     66.00  91.00   0.50    0.50    --   94.60  74.00-154.99   50
 32  \w     67.00  93.00   0.50    0.50    --   94.60  71.00 131.96   52
 33  \w     72.00 136.00   0.50    0.50    --   94.60  68.00 100.83  128
 34  \w     35.00 124.00   0.50    0.50    --   94.60 -82.00-180.00  178
 35  \w     68.00  94.00   0.50    0.50    --   94.60  69.00 149.58   52
 36  \w     71.00 149.00   0.50    0.50    --   94.60  62.00  71.22  156
 37  \w      5.00 114.00   0.50    0.50    --   94.60 -82.00  60.00  218
 38  \w    116.00 143.00   0.50    0.50    --   94.60  69.00  -0.01   54
 39  \w     67.00  92.00   0.50    0.50    --   94.60  73.00-114.86   50
 40  \w    101.00 131.00   0.50    0.50    --   94.60  68.00-167.69   60
 41  \w     71.00  96.00   0.50    0.50    --   94.60  61.00-120.00   50
 42  \w     13.00  41.00   0.50    0.50    --   94.60 -77.00-150.00   56
 43  \w     52.00  93.00   0.50    0.50    --   94.60 -77.00-150.00   82
 44  \w     71.00 178.00   0.50    0.50    --   94.60  61.00 -60.00  214
 45  \w      5.00  97.00   0.50    0.50    --   94.60 -61.00  60.00  184
 46  \w     75.00 107.00   0.50    0.50    --   94.60  45.00-120.00   64
 47  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 120.00   50
 48  \w     72.00  98.00   0.50    0.50    --   94.60  55.00 176.37   52
 49  \w     67.00  93.00   0.50    0.50    --   94.60  71.00 112.48   52
 50  \w     69.00  94.00   0.50    0.50    --   94.60  68.00-167.69   50
 51  \w     66.00 171.00   0.50    0.50    --   94.60  74.00 -28.57  210
 52  \w     71.00 144.00   0.50    0.50    --   94.60  61.00  60.00  146
 53  \w     71.00 140.00   0.50    0.50    --   94.60  61.00-150.00  138
 54  \w     71.00 173.00   0.50    0.50    --   94.60  61.00 -90.00  204
 55  \w     19.00 119.00   0.50    0.50    --   94.60 -82.00 -60.00  200
 56  \w    103.00 129.00   0.50    0.50    --   94.60  71.00 178.11   52
 57  \w     68.00  98.00   0.50    0.50    --   94.60  69.00  -0.01   60
 58  \w     71.00 118.00   0.50    0.50    --   94.60  61.00 -40.76   94
 59  \w     67.00  93.00   0.50    0.50    --   94.60  72.00 137.16   52
 60  \w     72.00  98.00   0.50    0.50    --   94.60  61.00 -30.00   52
 61  \w      6.00 107.00   0.50    0.50    --   94.60 -61.00 -60.00  202
 62  \w     67.00  93.00   0.50    0.50    --   94.60  71.00-144.59   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0095482000
_diffrn_orient_matrix_UB_12      0.1783144000
_diffrn_orient_matrix_UB_13      -0.0004059000
_diffrn_orient_matrix_UB_21      -0.0042173000
_diffrn_orient_matrix_UB_22      0.0020855000
_diffrn_orient_matrix_UB_23      0.0325886000
_diffrn_orient_matrix_UB_31      0.2016603000
_diffrn_orient_matrix_UB_32      0.0084999000
_diffrn_orient_matrix_UB_33      0.0006658000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_number            74104
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.962
_diffrn_reflns_theta_min         3.741
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.190
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2592 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         6207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0217
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0304P)^2^+0.8893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0563
_refine_ls_wR_factor_ref         0.0564
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                6182
_reflns_number_total             6207
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b01862_si_004.cif
_cod_data_source_block           20181229_9008
_cod_database_code               4128759
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.862
_shelx_estimated_absorpt_t_min   0.559
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2.a Ternary CH refined with riding coordinates:
 C5(H5), C8(H8), C10(H10), C12(H12), C13(H13), C15(H15), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4A), C14(H14), C16(H16), C17(H17), C20(H20), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C21(H21A,H21B,H21C), C24(H24A,H24B,
 H24C), C26(H26A,H26B,H26C)
;
_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 1.416
_oxdiff_exptl_absorpt_empirical_full_min 0.771