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_1568120
_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         'C9 H6 N O7 Re'
_chemical_formula_sum            'C9 H6 N O7 Re'
_chemical_formula_weight         426.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-16
_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                88.048(3)
_cell_angle_beta                 76.353(3)
_cell_angle_gamma                84.465(4)
_cell_formula_units_Z            2
_cell_length_a                   7.2397(3)
_cell_length_b                   8.0044(4)
_cell_length_c                   9.5362(2)
_cell_measurement_reflns_used    10143
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.7350
_cell_measurement_theta_min      4.7610
_cell_volume                     534.48(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 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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     29.00 125.00   0.50    0.12    --   51.79  77.00   0.00  192
  2  \w     92.00 178.00   0.50    0.49    --  107.75  61.00 120.00  172
  3  \w     95.00 178.00   0.50    0.49    --  107.75  16.00 144.00  166
  4  \w     40.00 132.00   0.50    0.12    --   51.79  16.00 144.00  184
  5  \w     29.00 125.00   0.50    0.12    --   51.79  77.00 -60.00  192
  6  \w     29.00 125.00   0.50    0.12    --   51.79  77.00-120.00  192
  7  \w     95.00 178.00   0.50    0.49    --  107.75  45.00-180.00  166
  8  \w     34.00 130.00   0.50    0.49    --  107.75 -77.00  60.00  192
  9  \w     37.00 124.00   0.50    0.49    --  107.75 -61.00  60.00  174
 10  \w     37.00 124.00   0.50    0.49    --  107.75 -61.00 150.00  174
 11  \w     32.00 120.00   0.50    0.49    --  107.75 -45.00  60.00  176
 12  \w     37.00 124.00   0.50    0.49    --  107.75 -61.00 -60.00  174
 13  \w    -21.00  67.00   0.50    0.12    --   51.79 -57.00-180.00  176
 14  \w     34.00 130.00   0.50    0.49    --  107.75 -77.00-180.00  192
 15  \w     28.00 120.00   0.50    0.49    --  107.75 -16.00 -25.00  184
 16  \w     30.00 120.00   0.50    0.49    --  107.75 -30.00-180.00  180
 17  \w     28.00 120.00   0.50    0.49    --  107.75 -15.00-180.00  184
 18  \w    -27.00  65.00   0.50    0.12    --   51.79 -16.00 -25.00  184
 19  \w     31.00 106.00   0.50    0.49    --  107.75 -94.00 -30.00  150
 20  \w     31.00 106.00   0.50    0.49    --  107.75 -94.00  30.00  150
 21  \w     31.00 109.00   0.50    0.49    --  107.75-111.00  30.00  156
 22  \w     31.00 106.00   0.50    0.49    --  107.75 -94.00  60.00  150
 23  \w     31.00 109.00   0.50    0.49    --  107.75-111.00 -60.00  156
 24  \w     31.00 109.00   0.50    0.49    --  107.75-111.00-120.00  156
 25  \w    -83.00  -9.00   0.50    0.49    --  -86.25 111.00 -90.00  148
 26  \w    -65.00  28.00   0.50    0.12    --  -51.79  16.00 144.00  186
 27  \w    -99.00  -6.00   0.50    0.49    --  -86.25  16.00 144.00  186
 28  \w   -132.00 -39.00   0.50    0.12    --  -51.79 -16.00 -25.00  186
 29  \w   -166.00 -73.00   0.50    0.49    --  -86.25 -16.00 -25.00  186
 30  \w   -125.00 -29.00   0.50    0.12    --  -51.79 -77.00 -90.00  192
 31  \w   -125.00 -29.00   0.50    0.12    --  -51.79 -77.00  90.00  192
 32  \w   -124.00 -37.00   0.50    0.12    --  -51.79 -57.00 150.00  174
 33  \w   -126.00 -73.00   0.50    0.12    --  -51.79-125.00  30.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1277555000
_diffrn_orient_matrix_UB_12      -0.1609001000
_diffrn_orient_matrix_UB_13      0.0179445000
_diffrn_orient_matrix_UB_21      -0.1756919000
_diffrn_orient_matrix_UB_22      -0.1016280000
_diffrn_orient_matrix_UB_23      0.0301875000
_diffrn_orient_matrix_UB_31      0.0340836000
_diffrn_orient_matrix_UB_32      -0.0343341000
_diffrn_orient_matrix_UB_33      -0.1625018000
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10649
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.492
_diffrn_reflns_theta_min         4.772
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    22.569
_exptl_absorpt_correction_T_max  0.714
_exptl_absorpt_correction_T_min  0.115
_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            colourless
_exptl_crystal_density_diffrn    2.649
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.542
_refine_diff_density_min         -1.160
_refine_diff_density_rms         0.171
_refine_ls_extinction_coef       0.00099(15)
_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   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0218
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0390P)^2^+0.7536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0589
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2116
_reflns_number_total             2165
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           38
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_database_code               1568120
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.661
_shelx_estimated_absorpt_t_min   0.074
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Rotating group:
 O4(H4A,H4B), O5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5A), C6(H6), C7(H7)
;
_shelx_res_checksum              83606
_shelx_hkl_checksum              3426