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_1568114
_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, H2 O'
_chemical_formula_sum            'C10 H10 N O8 Re'
_chemical_formula_weight         458.39
_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             2021-04-29
_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                 94.0710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.61350(10)
_cell_length_b                   11.21590(10)
_cell_length_c                   9.56510(10)
_cell_measurement_reflns_used    22994
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.3870
_cell_measurement_theta_min      3.5470
_cell_volume                     2633.90(4)
_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 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   -116.00 -20.00   0.80    6.00    --  -42.61 -37.00 -90.00  120
  2  \w    -80.00  36.00   0.80    6.00    --  -42.61  19.00  90.00  145
  3  \w    -87.00  -7.00   0.80    6.00    --  -42.61 125.00  60.00  100
  4  \w     11.00  40.60   0.80    6.00    --   42.61  76.00  42.92   37
  5  \w     10.00  42.00   0.80    6.00    --   42.61  81.00   8.77   40
  6  \w      6.00  82.00   0.80    6.00    --   42.61 -99.00 150.00   95
  7  \w     10.00  42.00   0.80    6.00    --   42.61  82.00-139.83   40
  8  \w     11.00  40.60   0.80    6.00    --   42.61  79.00-102.24   37
  9  \w     11.00  40.60   0.80    6.00    --   42.61  79.00 -79.18   37
 10  \w     30.00 106.00   0.80   24.00    --  111.00 -94.00 120.00   95
 11  \w    104.00 177.60   0.80   24.00    --  111.00 111.00  90.00   92
 12  \w     36.00 134.40   0.80   24.00    --  111.00 -30.00 120.00  123
 13  \w     30.00 106.00   0.80   24.00    --  111.00 -94.00   0.00   95
 14  \w    104.00 177.60   0.80   24.00    --  111.00 111.00  30.00   92
 15  \w     30.00 106.00   0.80   24.00    --  111.00 -94.00 -30.00   95
 16  \w     81.00 177.00   0.80   24.00    --  111.00  71.00 -91.50  120
 17  \w     30.00 106.00   0.80   24.00    --  111.00 -94.00  30.00   95
 18  \w     61.00 145.00   0.80   24.00    --  111.00 178.00-180.00  105
 19  \w    104.00 177.60   0.80   24.00    --  111.00 111.00 -60.00   92
 20  \w     41.00 126.60   0.80   24.00    --  111.00-144.00  96.30  107
 21  \w     36.00 108.00   0.80   24.00    --  111.00-111.00 -30.00   90
 22  \w     81.00 177.00   0.80   24.00    --  111.00  70.00 131.91  120
 23  \w     36.00 108.00   0.80   24.00    --  111.00-111.00 120.00   90
 24  \w    104.00 177.60   0.80   24.00    --  111.00 111.00-180.00   92
 25  \w     61.00 145.00   0.80   24.00    --  111.00 178.00 -60.00  105
 26  \w     37.00 141.00   0.80   24.00    --  111.00 -77.00-120.00  130
 27  \w    103.00 177.40   0.80   24.00    --  111.00  77.00-150.00   93
 28  \w     36.00 108.00   0.80   24.00    --  111.00-111.00-120.00   90
 29  \w     36.00 108.00   0.80   24.00    --  111.00-111.00  90.00   90
 30  \w     36.00 108.00   0.80   24.00    --  111.00-111.00 -60.00   90
 31  \w     83.00 177.40   0.80   24.00    --  111.00  62.00 163.87  118
 32  \w    104.00 177.60   0.80   24.00    --  111.00 111.00  60.00   92
 33  \w     36.00 108.00   0.80   24.00    --  111.00-111.00-180.00   90
 34  \w     36.00 108.00   0.80   24.00    --  111.00-111.00  60.00   90
 35  \w     34.00 106.80   0.80   24.00    --  111.00-106.00-109.36   91
 36  \w   -113.00 -17.00   0.80    6.00    --  -42.61 -57.00-180.00  120
 37  \w   -116.00 -20.00   0.80    6.00    --  -42.61 -37.00  60.00  120
 38  \w   -114.00 -19.60   0.80    6.00    --  -42.61 -42.00 -13.00  118
 39  \w     11.00  40.60   0.80    6.00    --   42.61  78.00 178.69   37
 40  \w     11.00  40.60   0.80    6.00    --   42.61  77.00 -44.49   37
 41  \w      6.00  82.00   0.80    6.00    --   42.61 -99.00 -60.00   95
 42  \w    -30.00  64.40   0.80    6.00    --   42.61 -37.00 150.00  118
 43  \w     11.00  40.60   0.80    6.00    --   42.61  78.00 116.87   37
 44  \w     66.00 178.00   0.80   24.00    --  111.00  15.00  30.00  140
;
_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      0.0124446000
_diffrn_orient_matrix_UB_12      -0.0256650000
_diffrn_orient_matrix_UB_13      -0.1527413000
_diffrn_orient_matrix_UB_21      -0.0383838000
_diffrn_orient_matrix_UB_22      -0.1086061000
_diffrn_orient_matrix_UB_23      -0.0026069000
_diffrn_orient_matrix_UB_31      -0.0480318000
_diffrn_orient_matrix_UB_32      0.0800832000
_diffrn_orient_matrix_UB_33      -0.0524157000
_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  0.0161
_diffrn_reflns_av_unetI/netI     0.0060
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            25893
_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         74.460
_diffrn_reflns_theta_min         3.601
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    18.440
_exptl_absorpt_correction_T_max  0.621
_exptl_absorpt_correction_T_min  0.293
_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    2.312
_exptl_crystal_description       plate
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.000273(7)
_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     200
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.215
_refine_ls_R_factor_all          0.0123
_refine_ls_R_factor_gt           0.0123
_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^)+(0.0140P)^2^+4.7315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0309
_refine_ls_wR_factor_ref         0.0309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2683
_reflns_number_total             2686
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           29
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_database_code               1568114
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.608
_shelx_estimated_absorpt_t_min   0.288
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All H(H,H,H) groups, All C(H,H,H) groups
2. Restrained distances
 O8-H8A = O8-H8C
 0.82 with sigma of 0.01
 O8-H8B
 0.82 with sigma of 0.01
3. Others
 Fixed Sof: H8B(0.5) H8C(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              48530
_shelx_hkl_checksum              4089