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_1568115
_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 F N O6 Re, 0.5(C H4 O)'
_chemical_formula_sum            'C9.5 H7 F N O6.5 Re'
_chemical_formula_weight         444.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                78.502(2)
_cell_angle_beta                 68.184(2)
_cell_angle_gamma                73.235(2)
_cell_formula_units_Z            4
_cell_length_a                   9.7973(2)
_cell_length_b                   10.6398(3)
_cell_length_c                   12.7440(3)
_cell_measurement_reflns_used    18850
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.9540
_cell_measurement_theta_min      3.6970
_cell_volume                     1174.53(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 0.989
_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     29.00 125.00   0.50    0.10    --   51.79  77.00 -30.00  192
  2  \w     92.00 178.00   0.50    0.20    --  107.75  61.00-120.00  172
  3  \w     96.00 178.00   0.50    0.20    --  107.75  15.00 -30.00  164
  4  \w     94.00 137.00   0.50    0.20    --  107.75  30.00 150.00   86
  5  \w     96.00 178.00   0.50    0.20    --  107.75  15.00  60.00  164
  6  \w   -124.00 -37.00   0.50    0.10    --  -51.79 -57.00 -90.00  174
  7  \w   -125.00 -29.00   0.50    0.10    --  -51.79 -77.00   0.00  192
  8  \w   -125.00 -29.00   0.50    0.10    --  -51.79 -77.00  60.00  192
  9  \w   -125.00 -29.00   0.50    0.10    --  -51.79 -77.00 150.00  192
 10  \w    -83.00  -2.00   0.50    0.10    --  -51.79 112.00 -69.00  162
 11  \w    -83.00 -10.00   0.50    0.20    --  -86.25 112.00 -69.00  146
 12  \w   -157.00 -70.00   0.50    0.20    --  -86.25 -61.00  90.00  174
 13  \w   -124.00 -37.00   0.50    0.10    --  -51.79 -57.00  90.00  174
 14  \w   -159.00 -64.00   0.50    0.20    --  -86.25 -76.00 -84.16  190
 15  \w   -156.00 -69.00   0.50    0.20    --  -86.25 -64.00-151.73  174
 16  \w   -124.00 -37.00   0.50    0.10    --  -51.79 -57.00-180.00  174
 17  \w   -128.00 -80.00   0.50    0.10    --  -51.79-112.00-162.00   96
 18  \w   -162.00 -80.00   0.50    0.20    --  -86.25-112.00-162.00  164
 19  \w   -126.00 -73.00   0.50    0.10    --  -51.79-125.00  30.00  106
 20  \w     62.00 146.00   0.50    0.20    --  107.75 178.00  30.00  168
 21  \w    102.00 178.00   0.50    0.20    --  107.75 111.00 -30.00  152
 22  \w    102.00 178.00   0.50    0.20    --  107.75 111.00 -90.00  152
 23  \w    102.00 178.00   0.50    0.20    --  107.75 111.00-180.00  152
 24  \w    102.00 178.00   0.50    0.20    --  107.75 112.00 -69.00  152
 25  \w    102.00 178.00   0.50    0.20    --  107.75 111.00  90.00  152
 26  \w     37.00 124.00   0.50    0.20    --  107.75 -61.00 120.00  174
 27  \w     34.00  99.00   0.50    0.10    --   51.79-125.00  90.00  130
 28  \w     31.00 109.00   0.50    0.20    --  107.75-111.00 150.00  156
 29  \w     31.00 109.00   0.50    0.20    --  107.75-111.00 120.00  156
 30  \w     31.00 106.00   0.50    0.20    --  107.75 -94.00   0.00  150
 31  \w     24.00  93.00   0.50    0.10    --   51.79-112.00-162.00  138
 32  \w     32.00 109.00   0.50    0.20    --  107.75-112.00-162.00  154
 33  \w     31.00 109.00   0.50    0.20    --  107.75-111.00 -90.00  156
 34  \w     31.00 106.00   0.50    0.20    --  107.75 -94.00 -90.00  150
 35  \w     31.00 106.00   0.50    0.20    --  107.75 -94.00  30.00  150
 36  \w     31.00 106.00   0.50    0.20    --  107.75 -94.00  60.00  150
;
_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      0.0245998000
_diffrn_orient_matrix_UB_12      -0.1426735000
_diffrn_orient_matrix_UB_13      0.0572852000
_diffrn_orient_matrix_UB_21      -0.0412771000
_diffrn_orient_matrix_UB_22      0.0524268000
_diffrn_orient_matrix_UB_23      0.1148763000
_diffrn_orient_matrix_UB_31      -0.1675255000
_diffrn_orient_matrix_UB_32      0.0034024000
_diffrn_orient_matrix_UB_33      0.0257045000
_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  0.0326
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24608
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.450
_diffrn_reflns_theta_min         3.756
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    20.674
_exptl_absorpt_correction_T_max  0.739
_exptl_absorpt_correction_T_min  0.173
_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    2.513
_exptl_crystal_description       plate
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.174
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       0.00021(2)
_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   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0191
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0224P)^2^+1.9020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0483
_refine_ls_wR_factor_ref         0.0495
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4468
_reflns_number_total             4747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           22
_cod_depositor_comments
;
Adding full bibliography for 1568094--1568122.cif.

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C19 H14 F2 N2 O13 Re2'
_cod_original_formula_weight         888.72
_cod_original_formula_moiety         '2(C9 H5 F N O6 Re), C H4 O'
_cod_original_formula_units_Z            2
_cod_database_code               1568115
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.683
_shelx_estimated_absorpt_t_min   0.098
_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,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C13(H13), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              58117
_shelx_hkl_checksum              89443