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_1568110
_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         '2(C9 H7 N2 O6 Re), H2 O'
_chemical_formula_sum            'C18 H16 N4 O13 Re2'
_chemical_formula_weight         868.75
_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             2021-07-21
_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                82.284(2)
_cell_angle_beta                 87.5270(10)
_cell_angle_gamma                68.815(2)
_cell_formula_units_Z            4
_cell_length_a                   10.5868(2)
_cell_length_b                   13.4770(3)
_cell_length_c                   18.0923(3)
_cell_measurement_reflns_used    36172
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      73.3710
_cell_measurement_theta_min      2.4360
_cell_volume                     2385.09(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.986
_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  -7.00   0.80    3.00    --  -42.74 125.00 -60.00  100
  2  \w   -121.00  -6.60   0.80    3.00    --  -42.74 -19.00-150.00  143
  3  \w   -116.00 -20.00   0.80    3.00    --  -42.74 -37.00 120.00  120
  4  \w     11.00  40.60   0.80    3.00    --   42.74  78.00 103.63   37
  5  \w     27.00  97.40   0.80    3.00    --   42.74-125.00 -60.00   88
  6  \w     81.00 177.00   0.80   10.00    --  104.82  30.00  30.00  120
  7  \w    103.00 177.40   0.80   10.00    --  104.82  77.00  60.00   93
  8  \w     34.00 128.40   0.80   10.00    --  104.82 -45.00 -30.00  118
  9  \w     35.00 131.00   0.80   10.00    --  104.82 -61.00-180.00  120
 10  \w     33.00 113.00   0.80   10.00    --  104.82-125.00-150.00  100
 11  \w     97.00 175.40   0.80   10.00    --  104.82 125.00-120.00   98
 12  \w    103.00 177.40   0.80   10.00    --  104.82  77.00 -90.00   93
 13  \w     33.00 113.00   0.80   10.00    --  104.82-125.00 120.00  100
 14  \w     24.00 105.60   0.80   10.00    --  104.82 -94.00   0.00  102
 15  \w     24.00 105.60   0.80   10.00    --  104.82 -94.00 -60.00  102
 16  \w     75.00 176.60   0.80   10.00    --  104.82  71.00 -44.65  127
 17  \w    102.00 178.00   0.80   10.00    --  104.82 115.00 -11.00   95
 18  \w     28.00 108.00   0.80   10.00    --  104.82-105.00 -93.48  100
 19  \w   -113.00 -17.00   0.80    3.00    --  -42.74 -57.00  30.00  120
 20  \w    -69.00  27.00   0.80    3.00    --  -42.74  57.00-180.00  120
 21  \w     11.00  40.60   0.80    3.00    --   42.74  80.00 -39.63   37
 22  \w     11.00  40.60   0.80    3.00    --   42.74  79.00-104.34   37
 23  \w     10.00  42.00   0.80    3.00    --   42.74  81.00   1.19   40
 24  \w     81.00 177.00   0.80   10.00    --  104.82  30.00-120.00  120
 25  \w     77.00 174.60   0.80   10.00    --  104.82  61.00-120.00  122
 26  \w     81.00 177.00   0.80   10.00    --  104.82  30.00 150.00  120
 27  \w     77.00 174.60   0.80   10.00    --  104.82  63.00  39.45  122
 28  \w     75.00 175.00   0.80   10.00    --  104.82  69.00 -85.85  125
 29  \w     78.00 174.00   0.80   10.00    --  104.82  59.00 171.99  120
 30  \w     75.00 175.00   0.80   10.00    --  104.82  69.00 132.03  125
 31  \w     76.00 174.40   0.80   10.00    --  104.82  65.00  10.88  123
 32  \w     76.00 174.40   0.80   10.00    --  104.82  65.00 104.49  123
 33  \w     75.00 175.00   0.80   10.00    --  104.82  69.00  74.84  125
 34  \w     13.00 107.40   0.80    3.00    --   42.74  70.00 173.14  118
 35  \w     11.00  40.60   0.80    3.00    --   42.74  77.00  41.23   37
;
_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      0.0324722000
_diffrn_orient_matrix_UB_12      -0.0945496000
_diffrn_orient_matrix_UB_13      -0.0458694000
_diffrn_orient_matrix_UB_21      0.0512674000
_diffrn_orient_matrix_UB_22      -0.0795957000
_diffrn_orient_matrix_UB_23      0.0712039000
_diffrn_orient_matrix_UB_31      -0.1437841000
_diffrn_orient_matrix_UB_32      -0.0015478000
_diffrn_orient_matrix_UB_33      0.0144863000
_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  0.0191
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            44910
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.370
_diffrn_reflns_theta_min         2.465
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    20.238
_exptl_absorpt_correction_T_max  0.637
_exptl_absorpt_correction_T_min  0.211
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    2.419
_exptl_crystal_description       plate
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.310
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.000064(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL (Sheldrick, 2015b)'
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     729
_refine_ls_number_reflns         9457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0157
_refine_ls_R_factor_gt           0.0150
_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^)+(0.0148P)^2^+2.6749P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0353
_refine_ls_wR_factor_ref         0.0355
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9333
_reflns_number_total             9457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           10
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_database_code               1568110
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.688
_shelx_estimated_absorpt_t_min   0.195
_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,H,H,H,H,H,H,H,H,H,H,H,H,H,H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C22(H22), C23(H23),
 C24(H24), C31(H31), C32(H32), C33(H33)
;
_shelx_res_checksum              25747
_shelx_hkl_checksum              30882