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_1568101
_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 O6 Re'
_chemical_formula_sum            'C10 H8 N O6 Re'
_chemical_formula_weight         424.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-11
_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                 100.090(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.2924(2)
_cell_length_b                   11.1464(3)
_cell_length_c                   22.2675(6)
_cell_measurement_reflns_used    7026
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.6210
_cell_measurement_theta_min      4.0340
_cell_volume                     2270.73(10)
_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 0.998
_diffrn_measured_fraction_theta_max 0.991
_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     29.00 124.00   0.50    0.10    --   51.04  76.00  31.00  190
  2  \w     86.00 178.00   0.50    0.21    --  107.75  76.00  31.00  184
  3  \w     96.00 176.00   0.50    0.21    --  107.75  30.00 120.00  160
  4  \w    146.00 174.00   0.50    0.21    --  107.75  45.00-120.00   56
  5  \w    139.00 176.00   0.50    0.21    --  107.75  15.00-180.00   74
  6  \w     96.00 135.00   0.50    0.21    --  107.75  15.00-180.00   78
  7  \w     42.00  69.00   0.50    0.21    --  107.75 -94.00   0.00   54
  8  \w     46.00  91.00   0.50    0.21    --  107.75-111.00  90.00   90
  9  \w     65.00  92.00   0.50    0.21    --  107.75-111.00 120.00   54
 10  \w     36.00 101.00   0.50    0.21    --  107.75 -94.00  90.00  130
 11  \w     32.00 104.00   0.50    0.21    --  107.75 -94.00 -90.00  144
 12  \w     32.00  69.00   0.50    0.21    --  107.75 -94.00-180.00   74
 13  \w     29.00  58.00   0.50    0.21    --  107.75 -15.00-120.00   58
 14  \w    -22.00  73.00   0.50    0.10    --   51.04 -76.00 -94.00  190
 15  \w     35.00 130.00   0.50    0.21    --  107.75 -76.00 -94.00  190
 16  \w     34.00 120.00   0.50    0.21    --  107.75 -30.00 -90.00  172
 17  \w     74.00 115.00   0.50    0.21    --  107.75 -15.00-120.00   82
 18  \w    118.00 178.00   0.50    0.21    --  107.75 111.00-120.00  120
 19  \w    104.00 145.00   0.50    0.21    --  107.75 178.00 -90.00   82
 20  \w    -73.00  22.00   0.50    0.10    --  -51.04  76.00  31.00  190
 21  \w    -83.00 -12.00   0.50    0.10    --  -51.04 125.00 120.00  142
 22  \w   -108.00 -13.00   0.50    0.21    --  -86.25  76.00  31.00  190
 23  \w   -126.00 -73.00   0.50    0.10    --  -51.04-125.00   0.00  106
 24  \w   -126.00 -73.00   0.50    0.10    --  -51.04-125.00 -60.00  106
 25  \w   -126.00 -73.00   0.50    0.10    --  -51.04-125.00-180.00  106
 26  \w   -159.00 -64.00   0.50    0.21    --  -86.25 -76.00 -94.00  190
;
_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      -0.1379261000
_diffrn_orient_matrix_UB_12      -0.0018989000
_diffrn_orient_matrix_UB_13      -0.0497794000
_diffrn_orient_matrix_UB_21      -0.0582191000
_diffrn_orient_matrix_UB_22      -0.1089874000
_diffrn_orient_matrix_UB_23      0.0310176000
_diffrn_orient_matrix_UB_31      -0.0772282000
_diffrn_orient_matrix_UB_32      0.0850608000
_diffrn_orient_matrix_UB_33      0.0386779000
_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  0.0293
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10677
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.397
_diffrn_reflns_theta_min         4.033
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    21.174
_exptl_absorpt_correction_T_max  0.423
_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            colourless
_exptl_crystal_density_diffrn    2.483
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.911
_refine_diff_density_min         -1.486
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       0.000040(10)
_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   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0246
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0338P)^2^+16.7274P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0645
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2223
_reflns_number_total             2298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           15
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_original_cell_volume        2270.72(10)
_cod_database_code               1568101
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.417
_shelx_estimated_absorpt_t_min   0.101
_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
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              77793
_shelx_hkl_checksum              1589