Enantioselective inhibition of the SARS-CoV-2 main protease with rhenium(i) picolinic acid complexes.
Karges, Johannes; Giardini, Miriam A.; Blacque, Olivier; Woodworth, Brendon; Siqueira-Neto, Jair L; Cohen, Seth M.; Chemical science 14 (2023) 711–720; doi:10.1039/d2sc05473f

data_1568102
_publ_section_title
;
 Enantioselective inhibition of the SARS-CoV-2 main protease with
 rhenium(i) picolinic acid complexes.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              711
_journal_page_last               720
_journal_paper_doi               10.1039/d2sc05473f
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C10 H8 N O6 Re, 0.5(H2 O)'
_chemical_formula_sum            'C10 H9 N O6.5 Re'
_chemical_formula_weight         433.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-09-06 deposited with the CCDC.	2022-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.9160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   22.7527(2)
_cell_length_b                   10.61400(10)
_cell_length_c                   21.7337(2)
_cell_measurement_reflns_used    16471
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.0220
_cell_measurement_theta_min      3.4290
_cell_volume                     4934.72(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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   -116.00 -20.00   1.00    1.00    --  -42.61 -37.00 -90.00   96
  2  \w    -74.00  31.00   1.00    1.00    --  -42.61  77.00  30.00  105
  3  \w    -30.00  65.00   1.00    1.00    --   42.61 -37.00 -60.00   95
  4  \w     10.00  42.00   1.00    1.00    --   42.61  81.00 -82.38   32
  5  \w     36.00 109.00   1.00    4.00    --  111.00-111.00 -30.00   73
  6  \w     36.00 109.00   1.00    4.00    --  111.00-111.00 120.00   73
  7  \w     40.00 135.00   1.00    4.00    --  111.00 -45.00-120.00   95
  8  \w     83.00 178.00   1.00    4.00    --  111.00  61.00  30.00   95
  9  \w     36.00 109.00   1.00    4.00    --  111.00-111.00  90.00   73
 10  \w     36.00 109.00   1.00    4.00    --  111.00-111.00  30.00   73
 11  \w     38.00 110.00   1.00    4.00    --  111.00-119.00 -48.00   72
 12  \w     36.00 109.00   1.00    4.00    --  111.00-111.00  60.00   73
 13  \w    103.00 178.00   1.00    4.00    --  111.00  77.00 -30.00   75
 14  \w     36.00 109.00   1.00    4.00    --  111.00-111.00   0.00   73
 15  \w    103.00 178.00   1.00    4.00    --  111.00  77.00-120.00   75
 16  \w    104.00 178.00   1.00    4.00    --  111.00 111.00 -30.00   74
 17  \w    103.00 178.00   1.00    4.00    --  111.00  77.00   0.00   75
 18  \w   -121.00  -6.00   1.00    1.00    --  -42.61 -19.00   0.00  115
 19  \w     10.00  42.00   1.00    1.00    --   42.61  81.00  94.37   32
 20  \w     10.00  42.00   1.00    1.00    --   42.61  82.00 163.19   32
 21  \w     82.00 178.00   1.00    4.00    --  111.00  69.00 -68.23   96
 22  \w     66.00 178.00   1.00    4.00    --  111.00  15.00-150.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0047545000
_diffrn_orient_matrix_UB_12      0.1431556000
_diffrn_orient_matrix_UB_13      -0.0125723000
_diffrn_orient_matrix_UB_21      0.0337551000
_diffrn_orient_matrix_UB_22      -0.0153041000
_diffrn_orient_matrix_UB_23      -0.0501568000
_diffrn_orient_matrix_UB_31      -0.0634029000
_diffrn_orient_matrix_UB_32      -0.0188824000
_diffrn_orient_matrix_UB_33      -0.0548973000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            25330
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.482
_diffrn_reflns_theta_min         4.133
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    19.536
_exptl_absorpt_correction_T_max  0.553
_exptl_absorpt_correction_T_min  0.143
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.333
_exptl_crystal_description       plate
_exptl_crystal_F_000             3248
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.000036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         5046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0183
_refine_ls_R_factor_gt           0.0179
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0187P)^2^+12.6205P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0429
_refine_ls_wR_factor_ref         0.0431
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4989
_reflns_number_total             5046
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           5
_cod_depositor_comments
;
Adding full bibliography for 1568094--1568122.cif.

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C20 H18 N2 O13 Re2'
_cod_original_formula_weight         866.76
_cod_original_formula_moiety         '2(C10 H8 N O6 Re), H2 O'
_cod_original_formula_units_Z            8
_cod_database_code               1568102
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.592
_shelx_estimated_absorpt_t_min   0.158
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              31542
_shelx_hkl_checksum              19110