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_4128758
_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         'C43 H50 N2 O13 S'
_chemical_formula_sum            'C43 H50 N2 O13 S'
_chemical_formula_weight         834.91
_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_creation_date             2018-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.89374(2)
_cell_length_b                   26.14620(8)
_cell_length_c                   26.91187(8)
_cell_measurement_reflns_used    77833
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7930
_cell_measurement_theta_min      3.6920
_cell_volume                     4147.09(2)
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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     20.00  48.00   0.50    0.50    --    0.00  57.00-180.00   56
  2  \w    -79.00 -48.00   0.50    0.50    --    0.00 -38.00 -90.00   62
  3  \w    -78.00 -51.00   0.50    0.50    --    0.00 -38.00-150.00   54
  4  \w    -18.00  32.00   0.50    0.50    --    0.00  19.00  60.00  100
  5  \w     63.00  89.00   0.50    0.50    --    0.00  57.00-180.00   52
  6  \w    -40.00   9.00   0.50    0.50    --    0.00 -38.00 -90.00   98
  7  \w     38.00  64.00   0.50    0.50    --    0.00  19.00  60.00   52
  8  \w    -43.00  17.00   0.50    0.50    --    0.00 -38.00-150.00  120
  9  \w    -33.00  31.00   0.50    0.50    --    0.00 -82.00 150.00  128
 10  \w    -26.00  31.00   0.50    0.50    --    0.00 -82.00  30.00  114
 11  \w     57.00  83.00   0.50    0.50    --    0.00  57.00 150.00   52
 12  \w     25.00  53.00   0.50    0.50    --    0.00  57.00 150.00   56
 13  \w    -17.00  10.00   0.50    0.50    --    0.00  38.00-120.00   54
 14  \w     51.00  89.00   0.50    0.50    --    0.00  38.00-120.00   76
 15  \w    -22.00   3.00   0.50    0.50    --    0.00  57.00 150.00   50
 16  \w    -18.00   8.00   0.50    0.50    --    0.00  57.00-180.00   52
 17  \w     62.00  89.00   0.50    0.50    --    0.00  38.00 -90.00   54
 18  \w    -16.00  32.00   0.50    0.50    --    0.00  38.00 -90.00   96
 19  \w     72.00 128.00   0.50    0.50    --   94.60  57.00 -47.47  112
 20  \w     69.00 108.00   0.50    0.50    --   94.60  66.00 -84.26   78
 21  \w     69.00  94.00   0.50    0.50    --   94.60  66.00 -21.66   50
 22  \w     72.00 157.00   0.50    0.50    --   94.60  58.00  26.89  170
 23  \w     70.00 152.00   0.50    0.50    --   94.60  65.00  91.27  164
 24  \w     68.00  93.00   0.50    0.50    --   94.60  69.00   1.37   50
 25  \w     67.00  92.00   0.50    0.50    --   94.60  72.00 128.34   50
 26  \w     71.00 182.00   0.50    0.50    --   94.60  59.00-132.53  222
 27  \w     67.00  92.00   0.50    0.50    --   94.60  72.00 -57.51   50
 28  \w     70.00 183.00   0.50    0.50    --   94.60  64.00 -74.38  226
 29  \w     66.00  91.00   0.50    0.50    --   94.60  74.00  42.96   50
 30  \w     68.00  96.00   0.50    0.50    --   94.60  70.00-166.23   56
 31  \w     69.00 183.00   0.50    0.50    --   94.60  66.00 103.73  228
 32  \w     71.00 112.00   0.50    0.50    --   94.60  59.00  58.64   82
 33  \w     67.00  92.00   0.50    0.50    --   94.60  72.00 -77.01   50
 34  \w     68.00  93.00   0.50    0.50    --   94.60  70.00  70.64   50
 35  \w    154.00 180.00   0.50    0.50    --   94.60  57.00-177.07   52
 36  \w     71.00  96.00   0.50    0.50    --   94.60  60.00 133.92   50
 37  \w     72.00  97.00   0.50    0.50    --   94.60  57.00-177.07   50
 38  \w     12.00  65.00   0.50    0.50    --   94.60 -82.00 150.00  106
 39  \w     70.00 132.00   0.50    0.50    --   94.60  64.00  -1.85  124
 40  \w     71.00 157.00   0.50    0.50    --   94.60  60.00  74.01  172
 41  \w     78.00 104.00   0.50    0.50    --   94.60 -82.00 150.00   52
 42  \w     69.00 184.00   0.50    0.50    --   94.60  67.00 158.26  230
 43  \w     71.00 111.00   0.50    0.50    --   94.60  62.00  48.38   80
 44  \w     16.00 125.00   0.50    0.50    --   94.60 -82.00   0.00  218
 45  \w      5.00 124.00   0.50    0.50    --   94.60 -82.00-120.00  238
 46  \w      5.00 126.00   0.50    0.50    --   94.60 -82.00  60.00  242
 47  \w     69.00 183.00   0.50    0.50    --   94.60  66.00 -38.59  228
 48  \w     67.00  92.00   0.50    0.50    --   94.60  71.00 102.76   50
 49  \w     71.00  96.00   0.50    0.50    --   94.60  61.00-120.00   50
 50  \w     19.00 118.00   0.50    0.50    --   94.60 -61.00-120.00  198
 51  \w     68.00  93.00   0.50    0.50    --   94.60  69.00-111.11   50
 52  \w     71.00  96.00   0.50    0.50    --   94.60  60.00 156.37   50
 53  \w     71.00  96.00   0.50    0.50    --   94.60  61.00  90.00   50
 54  \w     70.00 105.00   0.50    0.50    --   94.60  65.00-147.76   70
 55  \w     73.00 144.00   0.50    0.50    --   94.60  53.00-157.90  142
 56  \w    141.00 178.00   0.50    0.50    --   94.60  60.00 141.59   74
 57  \w     68.00  94.00   0.50    0.50    --   94.60  73.00  84.24   52
 58  \w     69.00  94.00   0.50    0.50    --   94.60  66.00  21.64   50
 59  \w     66.00  92.00   0.50    0.50    --   94.60  74.00  20.85   52
 60  \w     67.00  93.00   0.50    0.50    --   94.60  75.00  53.71   52
 61  \w     66.00  91.00   0.50    0.50    --   94.60  75.00-109.56   50
 62  \w    131.00 174.00   0.50    0.50    --   94.60  57.00 -47.47   86
 63  \w     71.00  97.00   0.50    0.50    --   94.60  60.00 141.59   52
 64  \w     71.00 179.00   0.50    0.50    --   94.60  61.00-106.69  216
 65  \w     69.00 145.00   0.50    0.50    --   94.60  67.00 117.90  152
 66  \w     35.00  60.00   0.50    0.50    --   94.60 -82.00  90.00   50
 67  \w     97.00 124.00   0.50    0.50    --   94.60 -82.00  90.00   54
 68  \w     69.00 182.00   0.50    0.50    --   94.60  66.00 -11.37  226
;
_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      -0.0508100000
_diffrn_orient_matrix_UB_12      -0.0401488000
_diffrn_orient_matrix_UB_13      -0.0403853000
_diffrn_orient_matrix_UB_21      0.0645687000
_diffrn_orient_matrix_UB_22      -0.0430231000
_diffrn_orient_matrix_UB_23      0.0364694000
_diffrn_orient_matrix_UB_31      -0.2481577000
_diffrn_orient_matrix_UB_32      -0.0029945000
_diffrn_orient_matrix_UB_33      0.0177591000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            108935
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.978
_diffrn_reflns_theta_min         2.356
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.270
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55964
_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    1.337
_exptl_crystal_description       needle
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 3468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         8382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+1.1700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0643
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                8282
_reflns_number_total             8382
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b01862_si_003.cif
_cod_data_source_block           20181024_wrb_3_78_2
_cod_database_code               4128758
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.569
_reflns_odcompleteness_completeness 99.95
_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:
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00Q(H00Q), C00S(H00S),
 C00T(H00T), C012(H012), C017(H017)
2.b Secondary CH2 refined with riding coordinates:
 C00N(H00A,H00B), C00O(H00C,H00D), C00X(H00E,H00F), C00Y(H00G,H00H), C01M(H01V,
 H01W)
2.c Aromatic/amide H refined with riding coordinates:
 C00V(H00V), C00Z(H00Z), C010(H010), C011(H011), C013(H013), C015(H015),
 C016(H016), C018(H018), C019(H019), C01A(H01D), C01E(H01N), C01F(H01O),
 C01G(H01P), C01H(H01Q), C01I(H01R), C01J(H01S), C01K(H01T), C01L(H01U),
 C01N(H01X)
2.d Idealised Me refined as rotating group:
 C014(H01A,H01B,H01C), C01B(H01E,H01F,H01G), C01C(H01H,H01I,H01J), C01D(H01K,
 H01L,H01M)
;
_shelx_res_checksum              72163
_shelx_hkl_checksum              89544
_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 1.527
_oxdiff_exptl_absorpt_empirical_full_min 0.485