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_1568122
_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 H5 Cl N O6 Re'
_chemical_formula_sum            'C9 H5 Cl N O6 Re'
_chemical_formula_weight         444.79
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 91.5910(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   22.8800(2)
_cell_length_b                   9.98140(10)
_cell_length_c                   20.3649(2)
_cell_measurement_reflns_used    22732
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.9190
_cell_measurement_theta_min      3.8960
_cell_volume                     4649.03(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                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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     29.00 116.00   0.50    0.20    --   51.79  77.00  30.00  174
  2  \w     86.00 142.00   0.50    0.60    --  107.75  77.00 120.00  112
  3  \w     97.00 126.00   0.50    0.60    --  107.75  69.00  15.35   58
  4  \w    142.00 168.00   0.50    0.60    --  107.75  69.00  15.35   52
  5  \w     96.00 176.00   0.50    0.60    --  107.75  45.00 -30.00  160
  6  \w     95.00 173.00   0.50    0.60    --  107.75  30.00 -60.00  156
  7  \w    111.00 137.00   0.50    0.60    --  107.75 111.00 -30.00   52
  8  \w    110.00 177.00   0.50    0.60    --  107.75 111.00 -90.00  134
  9  \w    108.00 166.00   0.50    0.60    --  107.75 123.00-129.00  116
 10  \w     62.00 145.00   0.50    0.60    --  107.75 178.00 -90.00  166
 11  \w     98.00 123.00   0.50    0.60    --  107.75 149.00  33.00   50
 12  \w    129.00 167.00   0.50    0.60    --  107.75 111.00 120.00   76
 13  \w     31.00 106.00   0.50    0.60    --  107.75 -94.00   0.00  150
 14  \w     54.00 101.00   0.50    0.60    --  107.75-111.00 -30.00   94
 15  \w     81.00 117.00   0.50    0.60    --  107.75-149.00 -13.00   72
 16  \w     34.00  91.00   0.50    0.60    --  107.75 -94.00 -30.00  114
 17  \w     72.00  98.00   0.50    0.60    --  107.75-111.00-150.00   52
 18  \w     53.00  97.00   0.50    0.60    --  107.75 -94.00-150.00   88
 19  \w     31.00 105.00   0.50    0.60    --  107.75 -94.00-120.00  148
 20  \w     46.00 112.00   0.50    0.20    --   51.79-149.00 -13.00  132
 21  \w     71.00  96.00   0.50    0.60    --  107.75-123.00 149.00   50
 22  \w   -143.00-117.00   0.50    0.60    --  -86.25 -30.00  30.00   52
 23  \w   -127.00 -74.00   0.50    0.20    --  -51.79-123.00 149.00  106
 24  \w   -142.00-117.00   0.50    0.60    --  -86.25-123.00 149.00   50
 25  \w   -123.00 -56.00   0.50    0.20    --  -51.79-149.00 -13.00  134
 26  \w   -126.00 -91.00   0.50    0.20    --  -51.79-125.00 -60.00   70
 27  \w   -114.00 -63.00   0.50    0.20    --  -51.79 -57.00 -90.00  102
 28  \w    -85.00 -11.00   0.50    0.20    --  -51.79 123.00-129.00  148
 29  \w    -72.00 -47.00   0.50    0.60    --  -86.25 123.00-129.00   50
 30  \w   -104.00 -25.00   0.50    0.20    --  -51.79 149.00  33.00  158
 31  \w    -89.00 -64.00   0.50    0.60    --  -86.25 149.00  33.00   50
;
_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      -0.0660938000
_diffrn_orient_matrix_UB_12      0.0296303000
_diffrn_orient_matrix_UB_13      -0.0048296000
_diffrn_orient_matrix_UB_21      -0.0116540000
_diffrn_orient_matrix_UB_22      -0.1445524000
_diffrn_orient_matrix_UB_23      -0.0233428000
_diffrn_orient_matrix_UB_31      -0.0062608000
_diffrn_orient_matrix_UB_32      -0.0449281000
_diffrn_orient_matrix_UB_33      0.0718134000
_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  0.0211
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24897
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.503
_diffrn_reflns_theta_min         3.865
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    22.800
_exptl_absorpt_correction_T_max  0.510
_exptl_absorpt_correction_T_min  0.097
_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    2.542
_exptl_crystal_description       plate
_exptl_crystal_F_000             3296
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.635
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.000116(2)
_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   1.238
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4750
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.0156
_refine_ls_R_factor_gt           0.0152
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0111P)^2^+12.5556P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0355
_refine_ls_wR_factor_ref         0.0356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4723
_reflns_number_total             4750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           33
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_database_code               1568122
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.462
_shelx_estimated_absorpt_t_min   0.105
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H) groups
2. Restrained distances
 O4-H4B
 0.81 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16)
;
_shelx_res_checksum              40594
_shelx_hkl_checksum              99690