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_1568118
_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 N2 O6 Re, 1.5(H2 O)'
_chemical_formula_sum            'C10 H8 N2 O7.5 Re'
_chemical_formula_weight         462.38
_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             2021-03-24
_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                101.726(2)
_cell_angle_beta                 111.100(3)
_cell_angle_gamma                109.637(3)
_cell_formula_units_Z            4
_cell_length_a                   10.9380(3)
_cell_length_b                   11.4782(3)
_cell_length_c                   12.8234(3)
_cell_measurement_reflns_used    18113
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.3200
_cell_measurement_theta_min      3.9420
_cell_volume                     1314.84(8)
_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                 '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 0.994
_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    -69.00  27.00   0.80    1.00    --  -42.61  57.00-180.00  120
  2  \w    -74.00  30.00   0.80    1.00    --  -42.61  77.00 -60.00  130
  3  \w   -113.00 -17.00   0.80    1.00    --  -42.61 -57.00  30.00  120
  4  \w     10.00  42.00   0.80    1.00    --   42.61  81.00   4.31   40
  5  \w     11.00  40.60   0.80    1.00    --   42.61  77.00-145.88   37
  6  \w    -21.00  73.40   0.80    1.00    --   42.61 -77.00 -90.00  118
  7  \w     30.00 106.00   0.80    2.00    --  111.00 -94.00-150.00   95
  8  \w     41.00 138.60   0.80    2.00    --  111.00 -61.00 -60.00  122
  9  \w     36.00 108.00   0.80    2.00    --  111.00-111.00 120.00   90
 10  \w    104.00 177.60   0.80    2.00    --  111.00 111.00-120.00   92
 11  \w    104.00 177.60   0.80    2.00    --  111.00 111.00   0.00   92
 12  \w     36.00 108.00   0.80    2.00    --  111.00-111.00 -30.00   90
 13  \w     87.00 177.40   0.80    2.00    --  111.00  30.00-120.00  113
 14  \w     30.00 106.00   0.80    2.00    --  111.00 -94.00 -90.00   95
 15  \w     36.00 108.00   0.80    2.00    --  111.00-111.00-150.00   90
 16  \w     36.00 134.40   0.80    2.00    --  111.00 -30.00 -90.00  123
 17  \w     36.00 108.00   0.80    2.00    --  111.00-111.00  30.00   90
 18  \w     36.00 108.00   0.80    2.00    --  111.00-111.00  90.00   90
 19  \w    104.00 177.60   0.80    2.00    --  111.00 111.00 -90.00   92
 20  \w     36.00 134.40   0.80    2.00    --  111.00 -30.00-180.00  123
 21  \w     30.00 106.00   0.80    2.00    --  111.00 -94.00 150.00   95
 22  \w    103.00 177.40   0.80    2.00    --  111.00  77.00 120.00   93
 23  \w     87.00 177.40   0.80    2.00    --  111.00  45.00 -90.00  113
 24  \w     37.00 141.00   0.80    2.00    --  111.00 -77.00 -90.00  130
 25  \w    103.00 177.40   0.80    2.00    --  111.00  77.00  30.00   93
 26  \w     30.00 106.00   0.80    2.00    --  111.00 -94.00-120.00   95
 27  \w    104.00 177.60   0.80    2.00    --  111.00 111.00-150.00   92
 28  \w     87.00 177.40   0.80    2.00    --  111.00  30.00-180.00  113
 29  \w   -116.00 -20.00   0.80    1.00    --  -42.61 -37.00 -90.00  120
 30  \w   -113.00 -17.00   0.80    1.00    --  -42.61 -57.00 120.00  120
 31  \w    -65.00  29.40   0.80    1.00    --  -42.61  37.00  90.00  118
 32  \w     10.00  42.00   0.80    1.00    --   42.61  80.00  54.70   40
 33  \w     11.00  40.60   0.80    1.00    --   42.61  79.00-109.67   37
 34  \w     10.00  42.00   0.80    1.00    --   42.61  81.00 156.05   40
 35  \w     11.00  40.60   0.80    1.00    --   42.61  78.00 -67.33   37
 36  \w     83.00 177.40   0.80    2.00    --  111.00  64.00-172.63  118
 37  \w     83.00 177.40   0.80    2.00    --  111.00  61.00 120.00  118
 38  \w     83.00 177.40   0.80    2.00    --  111.00  61.00  30.00  118
 39  \w     83.00 177.40   0.80    2.00    --  111.00  61.00 -60.00  118
 40  \w     83.00 177.40   0.80    2.00    --  111.00  61.00  90.00  118
 41  \w     87.00 177.40   0.80    2.00    --  111.00  30.00   0.00  113
;
_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      0.1095121000
_diffrn_orient_matrix_UB_12      -0.0444858000
_diffrn_orient_matrix_UB_13      0.0732184000
_diffrn_orient_matrix_UB_21      -0.0982860000
_diffrn_orient_matrix_UB_22      -0.1440475000
_diffrn_orient_matrix_UB_23      -0.0913758000
_diffrn_orient_matrix_UB_31      0.0828264000
_diffrn_orient_matrix_UB_32      0.0279166000
_diffrn_orient_matrix_UB_33      -0.0740573000
_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  0.0236
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23312
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.495
_diffrn_reflns_theta_min         3.976
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    18.475
_exptl_absorpt_correction_T_max  0.461
_exptl_absorpt_correction_T_min  0.070
_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    2.336
_exptl_crystal_description       plate
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.200
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       0.00164(5)
_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   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         5341
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0198
_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^)+(0.0358P)^2^+0.7159P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0563
_refine_ls_wR_factor_ref         0.0566
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5213
_reflns_number_total             5341
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           26
_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            'C20 H16 N4 O15 Re2'
_cod_original_formula_weight         924.77
_cod_original_formula_moiety         '2(C10 H5 N2 O6 Re), 3(H2 O)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1314.84(7)
_cod_database_code               1568118
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.459
_shelx_estimated_absorpt_t_min   0.062
_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) groups, All O(H,H) groups
2. Restrained distances
 O10-H10A = O10-H10B = O4-H4B = O4-H4A
 0.82 with sigma of 0.01
 O14-H14B = O14-H14A = O15-H15B = O15-H15A
 0.82 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C14(H14), C16(H16), C17(H17)
;
_shelx_res_checksum              51623
_shelx_hkl_checksum              41012