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_1568116
_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           '-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             2021-03-15
_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                 97.9890(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.18810(10)
_cell_length_b                   11.06790(10)
_cell_length_c                   25.0097(3)
_cell_measurement_reflns_used    12874
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      79.1620
_cell_measurement_theta_min      3.5700
_cell_volume                     2518.63(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_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    102.00 178.00   0.50    0.20    --  110.00 111.00  90.00  152
  2  \w     96.00 178.00   0.50    0.20    --  110.00  30.00 -30.00  164
  3  \w     96.00 178.00   0.50    0.20    --  110.00  30.00 -60.00  164
  4  \w    106.00 178.00   0.50    0.20    --  110.00  98.00-128.00  144
  5  \w     34.00 123.00   0.50    0.10    --   49.87  57.00 -60.00  178
  6  \w    -81.00 -11.00   0.50    0.20    --  -88.50  98.00-128.00  140
  7  \w   -125.00 -73.00   0.50    0.10    --  -49.87-125.00 -90.00  104
  8  \w   -165.00 -85.00   0.50    0.20    --  -88.50 -98.00 124.00  160
  9  \w   -125.00 -73.00   0.50    0.10    --  -49.87-125.00-150.00  104
 10  \w    -80.00  28.00   0.50    0.10    --  -49.87  98.00-128.00  216
 11  \w     36.00 134.00   0.50    0.20    --  110.00 -77.00 -60.00  196
 12  \w     34.00 124.00   0.50    0.20    --  110.00 -45.00 -30.00  180
 13  \w     34.00 108.00   0.50    0.20    --  110.00-111.00 -60.00  148
 14  \w     34.00 107.00   0.50    0.20    --  110.00 -94.00 -60.00  146
 15  \w     34.00 108.00   0.50    0.20    --  110.00-111.00-150.00  148
 16  \w     34.00 107.00   0.50    0.20    --  110.00 -94.00-180.00  146
 17  \w     34.00 107.00   0.50    0.20    --  110.00 -94.00-120.00  146
 18  \w     -6.00  84.00   0.50    0.10    --   49.87 -98.00 124.00  180
 19  \w     34.00 107.00   0.50    0.20    --  110.00 -98.00 124.00  146
 20  \w     38.00 127.00   0.50    0.20    --  110.00 -61.00  60.00  178
;
_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      -0.0336750000
_diffrn_orient_matrix_UB_12      0.1310141000
_diffrn_orient_matrix_UB_13      -0.0185632000
_diffrn_orient_matrix_UB_21      -0.1460051000
_diffrn_orient_matrix_UB_22      -0.0049186000
_diffrn_orient_matrix_UB_23      0.0236743000
_diffrn_orient_matrix_UB_31      0.0788937000
_diffrn_orient_matrix_UB_32      0.0467339000
_diffrn_orient_matrix_UB_33      0.0544338000
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       31
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13080
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.493
_diffrn_reflns_theta_min         3.569
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    19.187
_exptl_absorpt_correction_T_max  0.308
_exptl_absorpt_correction_T_min  0.038
_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    2.333
_exptl_crystal_description       prism
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.452
_refine_diff_density_min         -1.101
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       0.000159(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   1.203
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2565
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.202
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0222
_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^)+(0.0268P)^2^+10.9719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0575
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2557
_reflns_number_total             2565
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           35
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_database_code               1568116
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.250
_shelx_estimated_absorpt_t_min   0.086
_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, All C(H,H,H,H) groups, All O(H) groups
2. Restrained distances
 O7-H7B \\sim O7-H7C
 with sigma of 0.005
3. Others
 Fixed Sof: H7B(0.5) H7C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
4.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              17987
_shelx_hkl_checksum              80312