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_1568103
_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, H2 O'
_chemical_formula_sum            'C10 H10 N O7 Re'
_chemical_formula_weight         442.39
_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             2021-03-31
_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                 97.3100(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.6859(3)
_cell_length_b                   11.41920(10)
_cell_length_c                   9.1451(2)
_cell_measurement_reflns_used    10069
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.1830
_cell_measurement_theta_min      3.5770
_cell_volume                     2556.99(7)
_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                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_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   -113.00 -16.00   0.50    0.50    --  -42.49 -57.00-120.00  194
  2  \w    -87.00  -6.00   0.50    0.50    --  -42.49 125.00-180.00  162
  3  \w     27.00  98.00   0.50    0.50    --   42.49-125.00 -60.00  142
  4  \w     27.00  98.00   0.50    0.50    --   42.49-125.00  90.00  142
  5  \w    -21.00  74.00   0.50    0.50    --   42.49 -77.00   0.00  190
  6  \w     36.00 109.00   0.50    1.50    --  111.00-111.00  90.00  146
  7  \w     41.00 139.00   0.50    1.50    --  111.00 -61.00  90.00  196
  8  \w     30.00 107.00   0.50    1.50    --  111.00 -94.00 -30.00  154
  9  \w    103.00 178.00   0.50    1.50    --  111.00  77.00-180.00  150
 10  \w    103.00 178.00   0.50    1.50    --  111.00  77.00 120.00  150
 11  \w    103.00 178.00   0.50    1.50    --  111.00  77.00  60.00  150
 12  \w     61.00 146.00   0.50    1.50    --  111.00 178.00-150.00  170
 13  \w     87.00 178.00   0.50    1.50    --  111.00  45.00 120.00  182
 14  \w     36.00 109.00   0.50    1.50    --  111.00-111.00-180.00  146
 15  \w    104.00 178.00   0.50    1.50    --  111.00 111.00 120.00  148
 16  \w     61.00 146.00   0.50    1.50    --  111.00 178.00 -30.00  170
 17  \w   -113.00 -16.00   0.50    0.50    --  -42.49 -57.00 120.00  194
 18  \w   -113.00 -16.00   0.50    0.50    --  -42.49 -57.00   0.00  194
 19  \w   -113.00 -16.00   0.50    0.50    --  -42.49 -57.00  60.00  194
 20  \w   -113.00 -16.00   0.50    0.50    --  -42.49 -57.00-180.00  194
 21  \w    -30.00  65.00   0.50    0.50    --   42.49 -37.00  90.00  190
 22  \w     87.00 134.00   0.50    1.50    --  111.00  30.00 -30.00   94
;
_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      -0.0276939000
_diffrn_orient_matrix_UB_12      -0.0658534000
_diffrn_orient_matrix_UB_13      -0.1364334000
_diffrn_orient_matrix_UB_21      0.0168842000
_diffrn_orient_matrix_UB_22      0.0984178000
_diffrn_orient_matrix_UB_23      -0.1002524000
_diffrn_orient_matrix_UB_31      0.0539079000
_diffrn_orient_matrix_UB_32      -0.0646593000
_diffrn_orient_matrix_UB_33      -0.0134466000
_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  0.0204
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12718
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.500
_diffrn_reflns_theta_min         3.610
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    18.899
_exptl_absorpt_correction_T_max  0.382
_exptl_absorpt_correction_T_min  0.051
_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    2.298
_exptl_crystal_description       plate
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.000188(11)
_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   1.216
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2609
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.0205
_refine_ls_R_factor_gt           0.0204
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0227P)^2^+13.9688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0519
_refine_ls_wR_factor_ref         0.0519
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2605
_reflns_number_total             2609
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           25
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_database_code               1568103
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.397
_shelx_estimated_absorpt_t_min   0.084
_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, All C(H,H,H) groups, All O(H,H,H) groups
2. Restrained distances
 O4-H4A = O4-H4B
 0.82 with sigma of 0.001
 O7-H7B = O7-H7C = O7-H7A
 0.82 with sigma of 0.01
3. Others
 Fixed Sof: H7A(0.5) H7B(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7)
4.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              28281
_shelx_hkl_checksum              50238