Design and synthesis of iso-<i>allo</i>-DNJ and L-isoDALDP derivatives: pursuit of potent and selective inhibitors of α-glucosidase.
Yang, Lin-Feng; Zhang, Ming; Shimadate, Yuna; Kato, Atsushi; Hou, Tian-Yang Liu; Li, Yi-Xian; Jia, Yue-Mei; Fleet, George W. J.; Yu, Chu-Yi; Organic & biomolecular chemistry 21 (2023) 3453–3464; doi:10.1039/d3ob00404j

data_7159282
_publ_section_title
;
 Design and synthesis of iso-<i>allo</i>-DNJ and L-isoDALDP derivatives:
 pursuit of potent and selective inhibitors of &#x3b1;-glucosidase.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3453
_journal_page_last               3464
_journal_paper_doi               10.1039/d3ob00404j
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H41 N O6 Si'
_chemical_formula_sum            'C33 H41 N O6 Si'
_chemical_formula_weight         575.76
_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
_audit_block_doi                 10.5517/ccdc.csd.cc2bl9v3
_audit_creation_date             2019-08-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-28 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.3990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.55970(10)
_cell_length_b                   10.58310(10)
_cell_length_c                   13.69520(10)
_cell_measurement_reflns_used    26251
_cell_measurement_temperature    169.99(13)
_cell_measurement_theta_max      74.7170
_cell_measurement_theta_min      3.3840
_cell_volume                     1589.79(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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      169.99(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_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   -122.00 -34.00   0.50    0.05    --  -47.20 -34.00 -71.00  176
  2  \w     34.00 122.00   0.50    0.05    --   47.20  34.00  86.00  176
  3  \w    -26.00  60.00   0.50    0.05    --   47.20 -34.00 -71.00  172
  4  \w   -112.00 -24.00   0.50    0.05    --  -99.00  34.00  86.00  176
  5  \w   -168.00 -86.00   0.50    0.05    --  -99.00 -34.00 -71.00  164
  6  \w     90.00 169.00   0.50    0.05    --  103.25  34.00  86.00  158
  7  \w     29.00 116.00   0.50    0.05    --  103.25 -34.00 -71.00  174
  8  \w   -120.00 -32.00   0.50    0.05    --  -47.20 -57.00-150.00  176
  9  \w    -60.00  27.00   0.50    0.05    --  -47.20  34.00  86.00  174
 10  \w     35.00 120.00   0.50    0.05    --   47.20  38.00 150.00  170
 11  \w     25.00 120.00   0.50    0.05    --   47.20  77.00-180.00  190
 12  \w     25.00 120.00   0.50    0.05    --   47.20  77.00-150.00  190
 13  \w     16.00  95.00   0.50    0.05    --   47.20-125.00-150.00  158
 14  \w   -168.00 -76.00   0.50    0.05    --  -99.00 -77.00-140.38  184
 15  \w   -168.00 -86.00   0.50    0.05    --  -99.00 -52.00 135.43  164
 16  \w   -112.00 -76.00   0.50    0.05    --  -99.00 -76.00-179.60   72
 17  \w   -106.00 -80.00   0.50    0.05    --  -99.00 -68.00-121.19   52
 18  \w   -109.00 -83.00   0.50    0.05    --  -99.00 -63.00-141.35   52
 19  \w   -106.00 -79.00   0.50    0.05    --  -99.00 -69.00-157.13   54
 20  \w   -110.00 -84.00   0.50    0.05    --  -99.00 -61.00-120.00   52
 21  \w   -112.00 -87.00   0.50    0.05    --  -99.00 -61.00 136.95   50
 22  \w   -107.00 -29.00   0.50    0.05    --  -99.00  45.00 -90.00  156
 23  \w   -106.00 -73.00   0.50    0.05    --  -99.00 -83.00 164.97   66
 24  \w   -168.00 -77.00   0.50    0.05    --  -99.00 -74.00 168.98  182
 25  \w   -115.00 -78.00   0.50    0.05    --  -99.00 -76.00 176.27   74
 26  \w   -104.00 -77.00   0.50    0.05    --  -99.00 -77.00-150.00   54
 27  \w   -102.00 -76.00   0.50    0.05    --  -99.00 -80.00-167.25   52
 28  \w    -98.00 -73.00   0.50    0.05    --  -99.00 -83.00-125.51   50
 29  \w   -149.00-123.00   0.50    0.05    --  -99.00 -76.00 176.27   52
 30  \w    -99.00 -73.00   0.50    0.05    --  -99.00 -83.00-152.95   52
 31  \w   -167.00 -89.00   0.50    0.05    --  -99.00 -47.00-130.53  156
 32  \w   -166.00 -88.00   0.50    0.05    --  -99.00 -55.00-109.37  156
 33  \w   -107.00 -80.00   0.50    0.05    --  -99.00 -68.00-125.72   54
 34  \w   -110.00 -84.00   0.50    0.05    --  -99.00 -55.00-163.75   52
 35  \w   -167.00 -86.00   0.50    0.05    --  -99.00 -47.00 177.94  162
 36  \w   -103.00 -77.00   0.50    0.05    --  -99.00 -80.00-161.04   52
 37  \w   -113.00 -24.00   0.50    0.05    --  -99.00  15.00 -90.00  178
 38  \w   -102.00 -77.00   0.50    0.05    --  -99.00 -77.00-120.00   50
 39  \w   -102.00 -77.00   0.50    0.05    --  -99.00 -77.00 -90.00   50
 40  \w     33.00 115.00   0.50    0.05    --  103.25 -45.00-180.00  164
 41  \w     33.00  99.00   0.50    0.05    --  103.25 -45.00  30.00  132
 42  \w     31.00 113.00   0.50    0.05    --  103.25-125.00-180.00  164
 43  \w     89.00 116.00   0.50    0.05    --  103.25 -45.00  60.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1111294000
_diffrn_orient_matrix_UB_12      0.0624839000
_diffrn_orient_matrix_UB_13      0.0193939000
_diffrn_orient_matrix_UB_21      -0.0645920000
_diffrn_orient_matrix_UB_22      0.0074343000
_diffrn_orient_matrix_UB_23      -0.1169068000
_diffrn_orient_matrix_UB_31      -0.0566228000
_diffrn_orient_matrix_UB_32      -0.1312855000
_diffrn_orient_matrix_UB_33      0.0024773000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30069
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.252
_diffrn_reflns_theta_min         3.401
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'lustrous light colourless'
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2706 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(7)
_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     376
_refine_ls_number_reflns         6247
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0296
_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^)+(0.0427P)^2^+0.3043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0786
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                6074
_reflns_number_total             6247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00404j2.cif
_cod_data_source_block           tx1201
_cod_depositor_comments
'Adding full bibliography for 7159278--7159282.cif.'
_cod_database_code               7159282
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNOSi
_reflns_odcompleteness_completeness 99.97
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C9(H9A,H9B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C),
 C25(H25A,H25B,H25C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              24623
_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 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.806