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_1568117
_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         '3(C9 H5 N2 O8 Re), H2 O'
_chemical_formula_sum            'C27 H17 N6 O25 Re3'
_chemical_formula_weight         1384.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-04
_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                 90.2970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.13580(10)
_cell_length_b                   18.60120(10)
_cell_length_c                   16.12660(10)
_cell_measurement_reflns_used    49870
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.5590
_cell_measurement_theta_min      2.3540
_cell_volume                     3640.38(4)
_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 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (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 1.000
_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    -87.00  -6.00   1.00    1.00    --  -41.94 125.00-180.00   81
  2  \w   -116.00 -18.00   1.00    1.00    --  -41.94 -37.00 -90.00   98
  3  \w    -70.00  31.00   1.00    1.00    --  -41.94  57.00-180.00  101
  4  \w    -66.00  33.00   1.00    1.00    --  -41.94  37.00  90.00   99
  5  \w      8.00  34.00   1.00    1.00    --   41.94  83.00 -11.78   26
  6  \w      8.00  42.00   1.00    1.00    --   41.94  82.00  65.40   34
  7  \w     36.00 109.00   1.00    2.00    --  112.00-111.00 120.00   73
  8  \w     29.00 107.00   1.00    2.00    --  112.00 -94.00  30.00   78
  9  \w     36.00 109.00   1.00    2.00    --  112.00-111.00 -60.00   73
 10  \w     36.00 109.00   1.00    2.00    --  112.00-111.00-150.00   73
 11  \w     36.00 109.00   1.00    2.00    --  112.00-111.00-180.00   73
 12  \w     36.00 109.00   1.00    2.00    --  112.00-111.00 150.00   73
 13  \w    104.00 178.00   1.00    2.00    --  112.00 111.00   0.00   74
 14  \w     83.00 178.00   1.00    2.00    --  112.00  59.00 171.43   95
 15  \w    103.00 178.00   1.00    2.00    --  112.00  77.00-180.00   75
 16  \w     36.00 109.00   1.00    2.00    --  112.00-111.00 -30.00   73
 17  \w    104.00 178.00   1.00    2.00    --  112.00 111.00  90.00   74
 18  \w    103.00 178.00   1.00    2.00    --  112.00  77.00 -90.00   75
 19  \w     36.00 145.00   1.00    2.00    --  112.00 -77.00   0.00  109
 20  \w     36.00 109.00   1.00    2.00    --  112.00-111.00  90.00   73
 21  \w     29.00 107.00   1.00    2.00    --  112.00 -94.00   0.00   78
 22  \w     36.00 109.00   1.00    2.00    --  112.00-111.00-120.00   73
 23  \w     85.00 178.00   1.00    2.00    --  112.00  52.00-104.98   93
 24  \w     29.00 107.00   1.00    2.00    --  112.00 -94.00 -30.00   78
 25  \w    103.00 178.00   1.00    2.00    --  112.00  77.00-150.00   75
 26  \w     36.00 109.00   1.00    2.00    --  112.00-111.00 -90.00   73
 27  \w     82.00 178.00   1.00    2.00    --  112.00  66.00  45.97   96
 28  \w     84.00 178.00   1.00    2.00    --  112.00  30.00 150.00   94
 29  \w     36.00 109.00   1.00    2.00    --  112.00-111.00   0.00   73
 30  \w    104.00 178.00   1.00    2.00    --  112.00 111.00  60.00   74
 31  \w   -116.00 -18.00   1.00    1.00    --  -41.94 -37.00 120.00   98
 32  \w    -87.00  -6.00   1.00    1.00    --  -41.94 125.00 -90.00   81
 33  \w   -116.00 -18.00   1.00    1.00    --  -41.94 -37.00  30.00   98
 34  \w      8.00  42.00   1.00    1.00    --   41.94  82.00-145.98   34
 35  \w      8.00  42.00   1.00    1.00    --   41.94  81.00 -92.55   34
 36  \w      8.00  34.00   1.00    1.00    --   41.94  83.00  40.59   26
 37  \w      9.00  42.00   1.00    1.00    --   41.94  79.00 155.05   33
 38  \w     83.00 137.00   1.00    2.00    --  112.00  59.00  26.75   54
 39  \w     82.00 178.00   1.00    2.00    --  112.00  65.00 -72.21   96
 40  \w     81.00 178.00   1.00    2.00    --  112.00  69.00-156.10   97
 41  \w     83.00 178.00   1.00    2.00    --  112.00  61.00   0.00   95
 42  \w     85.00 178.00   1.00    2.00    --  112.00  53.00  86.88   93
 43  \w     85.00 178.00   1.00    2.00    --  112.00  49.00 -20.00   93
;
_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      -0.1231517000
_diffrn_orient_matrix_UB_12      0.0169292000
_diffrn_orient_matrix_UB_13      0.0120794000
_diffrn_orient_matrix_UB_21      0.0286393000
_diffrn_orient_matrix_UB_22      0.0458629000
_diffrn_orient_matrix_UB_23      0.0767005000
_diffrn_orient_matrix_UB_31      0.0115538000
_diffrn_orient_matrix_UB_32      0.0668096000
_diffrn_orient_matrix_UB_33      -0.0556954000
_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  0.0309
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            71970
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.495
_diffrn_reflns_theta_min         3.627
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    20.072
_exptl_absorpt_correction_T_max  0.422
_exptl_absorpt_correction_T_min  0.061
_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    2.525
_exptl_crystal_description       needle
_exptl_crystal_F_000             2584
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.746
_refine_diff_density_min         -1.151
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       0.000244(5)
_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   1.263
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     600
_refine_ls_number_reflns         7431
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.269
_refine_ls_R_factor_all          0.0181
_refine_ls_R_factor_gt           0.0180
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0171P)^2^+5.1003P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0445
_refine_ls_wR_factor_ref         0.0446
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7403
_reflns_number_total             7431
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           41
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_database_code               1568117
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.379
_shelx_estimated_absorpt_t_min   0.068
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H,H) groups
2. Restrained distances
 O22A-N6 \\sim O22B-N6 \\sim O21B-N6 \\sim O21A-N6
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
O21A \\sim O21B \\sim O22A \\sim O22B: within 3A with sigma of 0.005 and sigma
for terminal atoms of 0.01 within 3A
4. Others
 Sof(O21B)=Sof(O22B)=1-FVAR(1)
 Sof(O21A)=Sof(O22A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16), C24(H24), C25(H25),
 C26(H26)
;
_shelx_res_checksum              90048
_shelx_hkl_checksum              4215