Synthesis of hydroxymethyl analogues of mannostatin A and their evaluation as inhibitors of GH38 α-mannosidases
Kalník, Martin; Zajičková, Mária; Kóňa, Juraj; Šesták, Sergej; Moncoľ, Ján; Koóš, Miroslav; Bella, Maroš; New Journal of Chemistry 45 (2021) 13539–13548; doi:10.1039/D1NJ02351A

data_7060803
_publ_section_title
;
 Synthesis of hydroxymethyl analogues of mannostatin A and their
 evaluation as inhibitors of GH38 \a-mannosidases
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13539
_journal_page_last               13548
_journal_paper_doi               10.1039/D1NJ02351A
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H28 O4'
_chemical_formula_sum            'C28 H28 O4'
_chemical_formula_weight         428.50
_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     direct
_audit_creation_date             2021-04-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-04-20 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.2340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7282(2)
_cell_length_b                   8.66640(10)
_cell_length_c                   14.9347(3)
_cell_measurement_reflns_used    92116
_cell_measurement_temperature    100
_cell_measurement_theta_max      73.59
_cell_measurement_theta_min      5.10
_cell_volume                     1123.01(4)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2014  (Burla et al.,  2007)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
 9731 frames, detector distance = 50 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0077
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            61296
_diffrn_reflns_point_group_measured_fraction_full 0.761
_diffrn_reflns_point_group_measured_fraction_max 0.739
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         73.135
_diffrn_reflns_theta_min         2.977
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  0.8261
_exptl_absorpt_correction_T_min  0.4836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   X-AREA
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         3315
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0250
_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^)+(0.0391P)^2^+0.1513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0629
_reflns_Friedel_coverage         0.388
_reflns_Friedel_fraction_full    0.485
_reflns_Friedel_fraction_max     0.444
_reflns_number_gt                3271
_reflns_number_total             3315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj02351a2.cif
_cod_data_source_block           ms289
_cod_depositor_comments          'Adding full bibliography for 7060803.cif.'
_cod_database_code               7060803
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.753
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.97(18)
 0.03(18)
2. 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
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              92112
_olex2_submission_special_instructions 'No special instructions were received'