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_1568109
_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         'C9 H5 N2 O8 Re, H2 O'
_chemical_formula_sum            'C9 H7 N2 O9 Re'
_chemical_formula_weight         473.37
_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             2021-03-17
_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                 102.6050(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.46680(10)
_cell_length_b                   24.4678(3)
_cell_length_c                   8.21830(10)
_cell_measurement_reflns_used    12683
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.7230
_cell_measurement_theta_min      3.6140
_cell_volume                     1269.03(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 (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 0.999
_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     86.00 178.00   0.50    0.20    --  107.75  76.00  39.00  184
  2  \w    104.00 132.00   0.50    0.20    --  107.75 111.00 -90.00   56
  3  \w    140.00 165.00   0.50    0.20    --  107.75 111.00 -90.00   50
  4  \w     95.00 178.00   0.50    0.20    --  107.75  45.00   0.00  166
  5  \w   -125.00 -30.00   0.50    0.10    --  -51.79 -76.00 -87.00  190
  6  \w   -126.00 -73.00   0.50    0.10    --  -51.79-125.00   0.00  106
  7  \w   -159.00 -64.00   0.50    0.20    --  -86.25 -76.00 -87.00  190
  8  \w    -21.00  74.00   0.50    0.10    --   51.79 -76.00 -87.00  190
  9  \w     34.00 130.00   0.50    0.20    --  107.75 -77.00 -30.00  192
 10  \w     35.00 130.00   0.50    0.20    --  107.75 -76.00 -87.00  190
 11  \w     28.00 120.00   0.50    0.20    --  107.75 -15.00-120.00  184
 12  \w     32.00 120.00   0.50    0.20    --  107.75 -45.00 -30.00  176
 13  \w     29.00 112.00   0.50    0.20    --  107.75 -15.00  30.00  166
 14  \w     30.00  93.00   0.50    0.20    --  107.75 -30.00 120.00  126
 15  \w    -74.00  21.00   0.50    0.10    --  -51.79  76.00  39.00  190
 16  \w   -108.00 -13.00   0.50    0.20    --  -86.25  76.00  39.00  190
 17  \w    -83.00  -9.00   0.50    0.20    --  -86.25 111.00 150.00  148
 18  \w     42.00  95.00   0.50    0.20    --  107.75 -94.00 120.00  106
 19  \w     36.00  87.00   0.50    0.20    --  107.75 -94.00 -90.00  102
;
_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      -0.0840645000
_diffrn_orient_matrix_UB_12      0.0476466000
_diffrn_orient_matrix_UB_13      -0.1185332000
_diffrn_orient_matrix_UB_21      0.1257028000
_diffrn_orient_matrix_UB_22      -0.0215581000
_diffrn_orient_matrix_UB_23      -0.1257551000
_diffrn_orient_matrix_UB_31      -0.1916944000
_diffrn_orient_matrix_UB_32      -0.0350393000
_diffrn_orient_matrix_UB_33      -0.0838954000
_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  0.0358
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13269
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.488
_diffrn_reflns_theta_min         3.613
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    19.257
_exptl_absorpt_correction_T_max  0.365
_exptl_absorpt_correction_T_min  0.040
_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            orange
_exptl_crystal_density_diffrn    2.478
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.092
_refine_diff_density_min         -1.283
_refine_diff_density_rms         0.206
_refine_ls_extinction_coef       0.00431(15)
_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   1.257
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2590
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.257
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0436P)^2^+2.2662P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0777
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2566
_reflns_number_total             2590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           31
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_database_code               1568109
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.308
_shelx_estimated_absorpt_t_min   0.053
_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 O(H,H) groups
2. Restrained distances
 O4-H4A = O9-H9A = O9-H9B
 0.82 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7)
;
_shelx_res_checksum              47532
_shelx_hkl_checksum              70336