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_1568113
_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 H6 N O8 Re'
_chemical_formula_sum            'C10 H6 N O8 Re'
_chemical_formula_weight         454.36
_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     direct
_audit_creation_date             2021-08-10
_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                 103.5150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.54130(10)
_cell_length_b                   6.84780(10)
_cell_length_c                   17.1068(2)
_cell_measurement_reflns_used    14601
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.1640
_cell_measurement_theta_min      2.6200
_cell_volume                     1200.65(3)
_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 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  -7.00   0.80    1.00    --  -42.49 125.00 120.00  100
  2  \w    -21.00  72.60   0.80    1.00    --   42.49 -77.00 -30.00  117
  3  \w     20.00 113.60   0.80    1.00    --   42.49  37.00  90.00  117
  4  \w     16.00 112.00   0.80    1.00    --   42.49  57.00 120.00  120
  5  \w     87.00 176.60   0.80    4.00    --  111.00  30.00   0.00  112
  6  \w     30.00 106.00   0.80    4.00    --  111.00 -94.00 -60.00   95
  7  \w     37.00 141.00   0.80    4.00    --  111.00 -77.00 150.00  130
  8  \w     87.00 176.60   0.80    4.00    --  111.00  30.00-120.00  112
  9  \w     30.00 106.00   0.80    4.00    --  111.00 -94.00 150.00   95
 10  \w     36.00 108.00   0.80    4.00    --  111.00-111.00  30.00   90
 11  \w     36.00 108.00   0.80    4.00    --  111.00-111.00  60.00   90
 12  \w     36.00 108.00   0.80    4.00    --  111.00-111.00 120.00   90
 13  \w     36.00 108.00   0.80    4.00    --  111.00-111.00   0.00   90
 14  \w    104.00 176.80   0.80    4.00    --  111.00 111.00-120.00   91
 15  \w     24.00 176.80   0.80    4.00    --  111.00   0.00   0.00  191
 16  \w     16.00 112.00   0.80    1.00    --   42.49  57.00-180.00  120
 17  \w    -30.00  63.60   0.80    1.00    --   42.49 -37.00   0.00  117
 18  \w     16.00 112.00   0.80    1.00    --   42.49  57.00-120.00  120
 19  \w     16.00 112.00   0.80    1.00    --   42.49  57.00 -30.00  120
 20  \w     83.00 176.60   0.80    4.00    --  111.00  61.00  30.00  117
 21  \w     87.00 176.60   0.80    4.00    --  111.00  45.00-180.00  112
 22  \w     66.00 178.00   0.80    4.00    --  111.00  15.00 150.00  140
 23  \w     83.00 156.60   0.80    4.00    --  111.00  61.00 -90.00   92
 24  \w     83.00 176.60   0.80    4.00    --  111.00  61.00  60.00  117
;
_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      0.0292139000
_diffrn_orient_matrix_UB_12      -0.2168429000
_diffrn_orient_matrix_UB_13      -0.0124768000
_diffrn_orient_matrix_UB_21      -0.1470706000
_diffrn_orient_matrix_UB_22      -0.0399068000
_diffrn_orient_matrix_UB_23      -0.0310016000
_diffrn_orient_matrix_UB_31      0.0105880000
_diffrn_orient_matrix_UB_32      0.0455781000
_diffrn_orient_matrix_UB_33      -0.0863487000
_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  0.0364
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14353
_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         74.430
_diffrn_reflns_theta_min         4.314
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    20.225
_exptl_absorpt_correction_T_max  0.252
_exptl_absorpt_correction_T_min  0.058
_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    2.514
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.092
_refine_diff_density_min         -1.160
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       0.00248(8)
_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   1.274
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2457
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.273
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0232
_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^)+(0.0255P)^2^+4.5954P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0595
_refine_ls_wR_factor_ref         0.0595
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2456
_reflns_number_total             2457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           37
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_database_code               1568113
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.214
_shelx_estimated_absorpt_t_min   0.081
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O4-H4A = O4-H4B = O8-H8
 0.82 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
;
_shelx_res_checksum              49221
_shelx_hkl_checksum              58223