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_7159281
_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         'Cl, C6 H14 N O4'
_chemical_formula_sum            'C6 H14 Cl N O4'
_chemical_formula_weight         199.63
_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_block_doi                 10.5517/ccdc.csd.cc2blb09
_audit_creation_date             2019-11-13
_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                   6.03620(10)
_cell_length_b                   11.5263(3)
_cell_length_c                   12.3169(3)
_cell_measurement_reflns_used    14921
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.5140
_cell_measurement_theta_min      2.3780
_cell_volume                     856.95(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.924
_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    -84.00  94.00   0.50    0.50    --    5.00  45.00  30.00  356
  2  \w    -84.00  94.00   0.50    0.50    --    5.00  45.00 106.61  356
  3  \w     31.00  94.00   0.50    0.50    --    5.00  45.00  45.96  126
  4  \w     67.00  94.00   0.50    0.50    --    5.00  45.00  90.00   54
  5  \w     68.00  94.00   0.50    0.50    --    5.00  45.00  60.00   52
  6  \w    -68.00 -14.00   0.50    0.50    --  -14.80  45.00  30.00  108
  7  \w   -103.00 -72.00   0.50    0.50    --  -14.80  45.00  30.00   62
  8  \w   -102.00  68.00   0.50    0.50    --  -14.80  45.00  60.00  340
  9  \w   -104.00 -47.00   0.50    0.50    --  -14.80  45.00 -19.07  114
 10  \w   -103.00  74.00   0.50    0.50    --  -14.80  45.00 120.00  354
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1081863000
_diffrn_orient_matrix_UB_12      -0.0032678000
_diffrn_orient_matrix_UB_13      0.0222615000
_diffrn_orient_matrix_UB_21      0.0458025000
_diffrn_orient_matrix_UB_22      -0.0104499000
_diffrn_orient_matrix_UB_23      0.0521604000
_diffrn_orient_matrix_UB_31      0.0018061000
_diffrn_orient_matrix_UB_32      0.0605203000
_diffrn_orient_matrix_UB_33      0.0102186000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20072
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.609
_diffrn_reflns_theta_min         2.420
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'intense colourless'
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 919 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.149(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0199
_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^)+(0.0271P)^2^+0.1945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0514
_refine_ls_wR_factor_ref         0.0515
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                2332
_reflns_number_total             2374
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00404j2.cif
_cod_data_source_block           mx8226
_cod_depositor_comments
'Adding full bibliography for 7159278--7159282.cif.'
_cod_database_code               7159281
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O1(H1), O3(H3)
2.b Ternary CH refined with riding coordinates:
 C1(H1C), C3(H3A)
2.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_shelx_res_checksum              97472
_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 1.534
_oxdiff_exptl_absorpt_empirical_full_min 0.428