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_1568108
_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 H6 N O7 Re, 0.5(H2 O)'
_chemical_formula_sum            'C9 H7 N O7.5 Re'
_chemical_formula_weight         435.35
_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             2021-07-13
_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                106.448(2)
_cell_angle_beta                 105.596(3)
_cell_angle_gamma                103.191(3)
_cell_formula_units_Z            4
_cell_length_a                   9.8967(3)
_cell_length_b                   10.5952(3)
_cell_length_c                   12.8653(2)
_cell_measurement_reflns_used    23190
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      79.0560
_cell_measurement_theta_min      3.8280
_cell_volume                     1176.62(7)
_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, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.993
_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     87.00 177.00   0.50    0.20    --  107.75  77.00 -73.81  180
  2  \w    137.00 178.00   0.50    0.20    --  107.75  45.00 -60.00   82
  3  \w     96.00 132.00   0.50    0.20    --  107.75  45.00 -60.00   72
  4  \w     95.00 178.00   0.50    0.20    --  107.75  45.00 -90.00  166
  5  \w     94.00 169.00   0.50    0.20    --  107.75  30.00-120.00  150
  6  \w     92.00 151.00   0.50    0.20    --  107.75  61.00-180.00  118
  7  \w     32.00  87.00   0.50    0.20    --  107.75 -94.00-120.00  110
  8  \w     32.00 110.00   0.50    0.20    --  107.75-119.00-144.00  156
  9  \w     30.00  96.00   0.50    0.10    --   51.79-119.00-144.00  132
 10  \w     50.00 120.00   0.50    0.10    --   51.79-157.00  60.00  140
 11  \w     50.00 134.00   0.50    0.20    --  107.75-157.00  60.00  168
 12  \w     48.00  75.00   0.50    0.20    --  107.75-111.00 120.00   54
 13  \w     31.00 109.00   0.50    0.20    --  107.75-111.00 150.00  156
 14  \w     78.00 109.00   0.50    0.20    --  107.75-111.00  90.00   62
 15  \w     31.00  73.00   0.50    0.20    --  107.75-111.00  90.00   84
 16  \w     33.00 109.00   0.50    0.20    --  107.75-111.00  60.00  152
 17  \w     42.00  75.00   0.50    0.20    --  107.75-111.00   0.00   66
 18  \w     79.00 109.00   0.50    0.20    --  107.75-111.00   0.00   60
 19  \w     42.00 105.00   0.50    0.20    --  107.75-111.00 -60.00  126
 20  \w     32.00  71.00   0.50    0.20    --  107.75-111.00-120.00   78
 21  \w     76.00 109.00   0.50    0.20    --  107.75-111.00-120.00   66
 22  \w     48.00 108.00   0.50    0.20    --  107.75-111.00-180.00  120
 23  \w     29.00 112.00   0.50    0.20    --  107.75 -15.00 -60.00  166
 24  \w     37.00 124.00   0.50    0.20    --  107.75 -61.00-150.00  174
 25  \w     38.00 110.00   0.50    0.20    --  107.75 -61.00 -60.00  144
 26  \w     50.00 124.00   0.50    0.20    --  107.75 -61.00   0.00  148
 27  \w    100.00 126.00   0.50    0.20    --  107.75 -77.00 120.00   52
 28  \w     55.00  81.00   0.50    0.20    --  107.75 -77.00 120.00   52
 29  \w     30.00  96.00   0.50    0.20    --  107.75 -15.00  30.00  132
 30  \w    128.00 164.00   0.50    0.20    --  107.75 111.00-120.00   72
 31  \w     98.00 178.00   0.50    0.20    --  107.75 119.00 -58.00  160
 32  \w     72.00 126.00   0.50    0.10    --   51.79 157.00  96.00  108
 33  \w     72.00 161.00   0.50    0.20    --  107.75 157.00  96.00  178
 34  \w    -99.00 -10.00   0.50    0.20    --  -86.25  45.00 -30.00  178
 35  \w   -109.00 -28.00   0.50    0.10    --  -51.79 157.00  96.00  162
 36  \w    -84.00  -8.00   0.50    0.10    --  -51.79 119.00 -58.00  152
 37  \w    -85.00 -10.00   0.50    0.20    --  -86.25 119.00 -58.00  150
 38  \w   -124.00 -37.00   0.50    0.10    --  -51.79 -57.00-120.00  174
 39  \w   -125.00 -29.00   0.50    0.10    --  -51.79 -77.00   0.00  192
 40  \w   -125.00 -29.00   0.50    0.10    --  -51.79 -77.00 150.00  192
 41  \w   -144.00 -51.00   0.50    0.20    --  -86.25-157.00  60.00  186
 42  \w   -126.00 -51.00   0.50    0.10    --  -51.79-157.00  60.00  150
 43  \w   -162.00 -76.00   0.50    0.20    --  -86.25-119.00-144.00  172
 44  \w   -128.00 -76.00   0.50    0.10    --  -51.79-119.00-144.00  104
;
_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      -0.1389995000
_diffrn_orient_matrix_UB_12      -0.0578753000
_diffrn_orient_matrix_UB_13      0.0266380000
_diffrn_orient_matrix_UB_21      0.0952634000
_diffrn_orient_matrix_UB_22      0.0545980000
_diffrn_orient_matrix_UB_23      0.1299151000
_diffrn_orient_matrix_UB_31      -0.0300521000
_diffrn_orient_matrix_UB_32      0.1394709000
_diffrn_orient_matrix_UB_33      0.0167282000
_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     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21833
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.485
_diffrn_reflns_theta_min         3.835
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    20.556
_exptl_absorpt_correction_T_max  0.325
_exptl_absorpt_correction_T_min  0.125
_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_colour_primary    yellow
_exptl_crystal_density_diffrn    2.458
_exptl_crystal_description       block
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.044
_refine_diff_density_min         -1.448
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       0.00133(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   1.182
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         4784
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0221
_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^)+(0.0261P)^2^+3.0030P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0562
_refine_ls_wR_factor_ref         0.0565
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4725
_reflns_number_total             4784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           8
_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            'C18 H14 N2 O15 Re2'
_cod_original_formula_weight         870.71
_cod_original_formula_moiety         '2(C9 H6 N O7 Re), H2 O'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1176.61(6)
_cod_database_code               1568108
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H14 N2 O15 Re2'
_chemical_oxdiff_usercomment     3-OH
_shelx_estimated_absorpt_t_max   0.233
_shelx_estimated_absorpt_t_min   0.128
_reflns_odcompleteness_completeness 99.34
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H) groups
2. Restrained distances
 O7-H7 = O4-H4B = O4-H4A = O11-H11A = O11-H11B = O14-H14A = O15-H15A = O15-H15B
 0.82 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15)
;
_shelx_res_checksum              8082
_shelx_hkl_checksum              62861
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.495
_oxdiff_exptl_absorpt_empirical_full_min 0.707