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_1568095
_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 O7 Re'
_chemical_formula_sum            'C10 H8 N O7 Re'
_chemical_formula_weight         440.37
_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             2021-07-08
_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                 108.801(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9487(3)
_cell_length_b                   6.8332(2)
_cell_length_c                   16.0682(4)
_cell_measurement_reflns_used    10011
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.8100
_cell_measurement_theta_min      2.8870
_cell_volume                     1241.93(6)
_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 0.986
_diffrn_measured_fraction_theta_max 0.982
_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    104.00 177.00   0.50    0.30    --  107.75  45.00  60.00  146
  2  \w    136.00 171.00   0.50    0.30    --  107.75  45.00  90.00   70
  3  \w     95.00 133.00   0.50    0.30    --  107.75  45.00  90.00   76
  4  \w     29.00 125.00   0.50    0.15    --   51.79  77.00-150.00  192
  5  \w    -80.00  24.00   0.50    0.15    --  -51.79  89.00 158.00  208
  6  \w    -80.00 -10.00   0.50    0.30    --  -86.25  89.00 158.00  140
  7  \w   -162.00 -78.00   0.50    0.30    --  -86.25 -89.00  42.00  168
  8  \w   -126.00 -73.00   0.50    0.15    --  -51.79-125.00-180.00  106
  9  \w   -128.00 -78.00   0.50    0.15    --  -51.79 -89.00  42.00  100
 10  \w     32.00 120.00   0.50    0.30    --  107.75 -45.00 150.00  176
 11  \w     81.00 106.00   0.50    0.30    --  107.75 -94.00 120.00   50
 12  \w     31.00 106.00   0.50    0.30    --  107.75 -94.00  90.00  150
 13  \w    -21.00  80.00   0.50    0.15    --   51.79 -89.00  42.00  202
 14  \w     32.00 106.00   0.50    0.30    --  107.75 -89.00  42.00  148
 15  \w     34.00 130.00   0.50    0.30    --  107.75 -77.00 120.00  192
 16  \w     31.00 106.00   0.50    0.30    --  107.75 -94.00 -30.00  150
 17  \w     41.00  66.00   0.50    0.30    --  107.75 -94.00-180.00   50
 18  \w     73.00 105.00   0.50    0.30    --  107.75 -94.00-180.00   64
 19  \w    100.00 178.00   0.50    0.30    --  107.75  89.00 158.00  156
 20  \w    102.00 178.00   0.50    0.30    --  107.75 111.00 120.00  152
 21  \w    102.00 178.00   0.50    0.30    --  107.75 111.00   0.00  152
 22  \w    102.00 178.00   0.50    0.30    --  107.75 111.00-120.00  152
;
_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      0.1285431000
_diffrn_orient_matrix_UB_12      -0.0344189000
_diffrn_orient_matrix_UB_13      0.0025775000
_diffrn_orient_matrix_UB_21      0.0350256000
_diffrn_orient_matrix_UB_22      0.2017196000
_diffrn_orient_matrix_UB_23      0.0432961000
_diffrn_orient_matrix_UB_31      0.0277758000
_diffrn_orient_matrix_UB_32      -0.0947405000
_diffrn_orient_matrix_UB_33      0.0914345000
_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  0.0381
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11246
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.432
_diffrn_reflns_theta_min         3.908
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    19.455
_exptl_absorpt_correction_T_max  0.657
_exptl_absorpt_correction_T_min  0.116
_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    2.355
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.842
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.203
_refine_ls_extinction_coef       0.00116(9)
_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   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2499
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+1.2329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2303
_reflns_number_total             2499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_database_code               1568095
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.697
_shelx_estimated_absorpt_t_min   0.077
_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. Restrained distances
 O4-H4A = O4-H4B
 0.82 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              70174
_shelx_hkl_checksum              81782