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_7159279
_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         'C10 H15 N O5'
_chemical_formula_sum            'C10 H15 N O5'
_chemical_formula_weight         229.23
_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.cc2bl9s1
_audit_creation_date             2019-12-13
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.50310(10)
_cell_length_b                   11.03120(10)
_cell_length_c                   11.53190(10)
_cell_measurement_reflns_used    10733
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.6370
_cell_measurement_theta_min      3.9600
_cell_volume                     1081.685(19)
_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      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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    -81.00  25.00   0.50    0.05    --  -47.20  99.00 174.00  212
  2  \w    -19.00  81.00   0.50    0.05    --   47.20 -99.00  68.00  200
  3  \w   -161.00-106.00   0.50    0.05    --  -99.00 -99.00  68.00  110
  4  \w    -82.00 -56.00   0.50    0.05    --  -99.00  99.00 174.00   52
  5  \w    101.00 143.00   0.50    0.05    --  103.25  99.00 174.00   84
  6  \w     53.00 100.00   0.50    0.05    --  103.25 -99.00  68.00   94
  7  \w   -115.00 -90.00   0.50    0.05    --  -47.20-125.00-150.00   50
  8  \w   -116.00 -89.00   0.50    0.05    --  -47.20-125.00-120.00   54
  9  \w   -113.00 -72.00   0.50    0.05    --  -47.20-125.00-180.00   82
 10  \w     25.00  50.00   0.50    0.05    --   47.20 -38.00 -30.00   50
 11  \w     91.00 120.00   0.50    0.05    --   47.20  57.00-120.00   58
 12  \w     30.00  57.00   0.50    0.05    --   47.20 -38.00  90.00   54
 13  \w    -25.00  14.00   0.50    0.05    --   47.20 -38.00  90.00   78
 14  \w    -18.00  23.00   0.50    0.05    --   47.20 -38.00 -30.00   82
 15  \w   -167.00 -81.00   0.50    0.05    --  -99.00 -94.00 -90.00  172
 16  \w    -90.00 -26.00   0.50    0.05    --  -99.00  77.00  90.00  128
 17  \w   -122.00 -96.00   0.50    0.05    --  -99.00  77.00  90.00   52
 18  \w   -158.00-104.00   0.50    0.05    --  -99.00 -45.00  90.00  108
 19  \w   -109.00 -25.00   0.50    0.05    --  -99.00  30.00-150.00  168
 20  \w   -167.00 -83.00   0.50    0.05    --  -99.00 -61.00   0.00  168
 21  \w    129.00 167.00   0.50    0.05    --  103.25 125.00-120.00   76
 22  \w     97.00 123.00   0.50    0.05    --  103.25  45.00 -60.00   52
 23  \w     97.00 169.00   0.50    0.05    --  103.25  30.00 150.00  144
 24  \w     73.00 109.00   0.50    0.05    --  103.25 -94.00   0.00   72
 25  \w     35.00 106.00   0.50    0.05    --  103.25 -94.00 150.00  142
 26  \w     31.00 117.00   0.50    0.05    --  103.25-125.00 -90.00  172
 27  \w     79.00 108.00   0.50    0.05    --  103.25 -94.00 -60.00   58
 28  \w     32.00  65.00   0.50    0.05    --  103.25 -94.00 -60.00   66
 29  \w     90.00 162.00   0.50    0.05    --  103.25  15.00 120.00  144
 30  \w    117.00 165.00   0.50    0.05    --  103.25  45.00 -90.00   96
;
_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      -0.1402881000
_diffrn_orient_matrix_UB_12      0.0684996000
_diffrn_orient_matrix_UB_13      -0.0535485000
_diffrn_orient_matrix_UB_21      -0.1038489000
_diffrn_orient_matrix_UB_22      -0.1133355000
_diffrn_orient_matrix_UB_23      0.0152524000
_diffrn_orient_matrix_UB_31      -0.0488832000
_diffrn_orient_matrix_UB_32      0.0443996000
_diffrn_orient_matrix_UB_33      0.1213495000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12265
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.143
_diffrn_reflns_theta_min         5.550
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.962
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75158
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 852 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0280
_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^)+(0.0424P)^2^+0.2006P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0766
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                2123
_reflns_number_total             2179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00404j2.cif
_cod_data_source_block           tx1795
_cod_depositor_comments
'Adding full bibliography for 7159278--7159282.cif.'
_cod_database_code               7159279
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         CHNOCl
_reflns_odcompleteness_completeness 99.83
_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(H1A), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C7(H7A,H7B)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              93022
_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 1.460
_oxdiff_exptl_absorpt_empirical_full_min 0.616