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_7159280
_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         'C9 H16 Cl N O3'
_chemical_formula_sum            'C9 H16 Cl N O3'
_chemical_formula_weight         221.68
_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   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2bl9r0
_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                 90.3845(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.36560(4)
_cell_length_b                   17.75841(12)
_cell_length_c                   9.71022(7)
_cell_measurement_reflns_used    11992
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      75.3430
_cell_measurement_theta_min      2.4050
_cell_volume                     1097.647(13)
_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(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.971
_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   -120.00 -72.00   0.50    0.05    --  -47.20-124.00-118.00   96
  2  \w   -107.00 -22.00   0.50    0.05    --  -47.20 147.00 125.00  170
  3  \w   -120.00 -56.00   0.50    0.05    --  -47.20-147.00  76.00  128
  4  \w     16.00  94.00   0.50    0.05    --   47.20-124.00-118.00  156
  5  \w     54.00 105.00   0.50    0.05    --   47.20-147.00  76.00  102
  6  \w   -103.00 -78.00   0.50    0.05    --  -99.00 147.00 125.00   50
  7  \w   -160.00-128.00   0.50    0.05    --  -99.00-124.00-118.00   64
  8  \w     94.00 132.00   0.50    0.05    --  103.25-147.00  76.00   76
  9  \w    100.00 144.00   0.50    0.05    --  103.25 124.00 -39.00   88
 10  \w     62.00 106.00   0.50    0.05    --  103.25 147.00 125.00   88
 11  \w     64.00 110.00   0.50    0.05    --  103.25-124.00-118.00   92
 12  \w     70.00 106.00   0.50    0.05    --   47.20  77.00 120.00   72
 13  \w    -25.00  59.00   0.50    0.05    --   47.20 -38.00  60.00  168
 14  \w     26.00 119.00   0.50    0.05    --   47.20  77.00  30.00  186
 15  \w   -120.00 -94.00   0.50    0.05    --  -99.00 -15.00 120.00   52
 16  \w   -162.00-129.00   0.50    0.05    --  -99.00 -45.00 -30.00   66
 17  \w   -109.00 -68.00   0.50    0.05    --  -99.00  61.00-180.00   82
 18  \w    -56.00 -27.00   0.50    0.05    --  -99.00  61.00-180.00   58
 19  \w   -112.00 -27.00   0.50    0.05    --  -99.00  45.00-180.00  170
 20  \w   -123.00 -97.00   0.50    0.05    --  -99.00 -45.00 -30.00   52
 21  \w   -161.00-133.00   0.50    0.05    --  -99.00 -15.00 120.00   56
 22  \w    -92.00 -25.00   0.50    0.05    --  -99.00  30.00   0.00  134
 23  \w     34.00  59.00   0.50    0.05    --  103.25 -45.00-150.00   50
 24  \w     62.00 116.00   0.50    0.05    --  103.25-125.00 120.00  108
 25  \w     76.00 114.00   0.50    0.05    --  103.25 -45.00-150.00   76
 26  \w     33.00 115.00   0.50    0.05    --  103.25 -45.00 -60.00  164
 27  \w     77.00 103.00   0.50    0.05    --  103.25 -94.00  60.00   52
 28  \w     92.00 162.00   0.50    0.05    --  103.25  45.00  30.00  140
 29  \w     35.00 120.00   0.50    0.05    --  103.25 -61.00-150.00  170
 30  \w     95.00 168.00   0.50    0.05    --  103.25  15.00 -30.00  146
;
_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      0.0011813000
_diffrn_orient_matrix_UB_12      -0.0852115000
_diffrn_orient_matrix_UB_13      -0.0299939000
_diffrn_orient_matrix_UB_21      0.0202759000
_diffrn_orient_matrix_UB_22      -0.0162783000
_diffrn_orient_matrix_UB_23      0.1553477000
_diffrn_orient_matrix_UB_31      -0.2411002000
_diffrn_orient_matrix_UB_32      -0.0018430000
_diffrn_orient_matrix_UB_33      0.0118731000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12093
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.151
_diffrn_reflns_theta_min         4.554
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.968
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80432
_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    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1918 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4261
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0273
_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^)+(0.0420P)^2^+0.2693P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0722
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                4197
_reflns_number_total             4261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00404j2.cif
_cod_data_source_block           tx1796
_cod_depositor_comments
'Adding full bibliography for 7159278--7159282.cif.'
_cod_database_code               7159280
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         CHNOCl
_reflns_odcompleteness_completeness 99.71
_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:
 C2(H2A), C4(H4A), C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C6(H6A,H6B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              19673
_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 1.225
_oxdiff_exptl_absorpt_empirical_full_min 0.820