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_1568112
_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 H5 F3 N O6 Re'
_chemical_formula_sum            'C10 H5 F3 N O6 Re'
_chemical_formula_weight         478.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-04
_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                 112.2060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.92600(10)
_cell_length_b                   6.81770(10)
_cell_length_c                   15.2153(2)
_cell_measurement_reflns_used    10876
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.2270
_cell_measurement_theta_min      3.1040
_cell_volume                     1241.41(3)
_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 2018/3 (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 0.999
_diffrn_measured_fraction_theta_max 0.992
_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   1.00    1.00    --  -42.61 -57.00  30.00   97
  2  \w      6.00  83.00   1.00    1.00    --   42.61 -99.00  90.00   77
  3  \w    -21.00  74.00   1.00    1.00    --   42.61 -77.00-120.00   95
  4  \w     11.00  42.00   1.00    1.00    --   42.61  77.00  -1.50   31
  5  \w     30.00 107.00   1.00    1.00    --  111.00 -94.00 -90.00   77
  6  \w     82.00 178.00   1.00    1.00    --  111.00  68.00 143.32   96
  7  \w     37.00 142.00   1.00    1.00    --  111.00 -77.00   0.00  105
  8  \w    103.00 178.00   1.00    1.00    --  111.00  77.00   0.00   75
  9  \w     39.00 111.00   1.00    1.00    --  111.00-121.00-115.00   72
 10  \w     36.00 109.00   1.00    1.00    --  111.00-111.00 120.00   73
 11  \w     36.00 109.00   1.00    1.00    --  111.00-111.00   0.00   73
 12  \w     36.00 109.00   1.00    1.00    --  111.00-111.00 -90.00   73
 13  \w     40.00 135.00   1.00    1.00    --  111.00 -45.00 -30.00   95
 14  \w     83.00 178.00   1.00    1.00    --  111.00  61.00 120.00   95
 15  \w   -116.00 -20.00   1.00    1.00    --  -42.61 -37.00 -60.00   96
 16  \w   -113.00 -16.00   1.00    1.00    --  -42.61 -57.00-150.00   97
 17  \w     10.00  42.00   1.00    1.00    --   42.61  81.00 141.98   32
 18  \w     87.00 178.00   1.00    1.00    --  111.00  30.00-120.00   91
 19  \w     82.00 178.00   1.00    1.00    --  111.00  69.00  62.78   96
 20  \w     81.00 178.00   1.00    1.00    --  111.00  71.00 -23.81   97
 21  \w     83.00 116.00   1.00    1.00    --  111.00  61.00-180.00   33
 22  \w     87.00 178.00   1.00    1.00    --  111.00  45.00 -60.00   91
;
_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      -0.0326872000
_diffrn_orient_matrix_UB_12      0.0619348000
_diffrn_orient_matrix_UB_13      0.0834948000
_diffrn_orient_matrix_UB_21      -0.0238467000
_diffrn_orient_matrix_UB_22      -0.2158298000
_diffrn_orient_matrix_UB_23      0.0157717000
_diffrn_orient_matrix_UB_31      0.1221215000
_diffrn_orient_matrix_UB_32      -0.0253937000
_diffrn_orient_matrix_UB_33      0.0688932000
_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  0.0263
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12810
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.312
_diffrn_reflns_theta_min         3.838
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    19.846
_exptl_absorpt_correction_T_max  0.518
_exptl_absorpt_correction_T_min  0.087
_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    2.559
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.00084(4)
_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   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0173
_refine_ls_R_factor_gt           0.0167
_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^)+(0.0264P)^2^+0.8546P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0436
_refine_ls_wR_factor_ref         0.0440
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2523
_reflns_number_total             2583
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           34
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_database_code               1568112
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.504
_shelx_estimated_absorpt_t_min   0.049
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
;
_shelx_res_checksum              79698
_shelx_hkl_checksum              75678