#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:04:58 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281396 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/81/1568101.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1568101
loop_
_publ_author_name
'Karges, Johannes'
'Giardini, Miriam A.'
'Blacque, Olivier'
'Woodworth, Brendon'
'Siqueira-Neto, Jair L'
'Cohen, Seth M.'
_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'
_chemical_formula_sum            'C10 H8 N O6 Re'
_chemical_formula_weight         424.37
_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             2021-05-11
_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                 100.090(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.2924(2)
_cell_length_b                   11.1464(3)
_cell_length_c                   22.2675(6)
_cell_measurement_reflns_used    7026
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.6210
_cell_measurement_theta_min      4.0340
_cell_volume                     2270.73(10)
_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 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00 124.00   0.50    0.10    --   51.04  76.00  31.00  190
  2  ω     86.00 178.00   0.50    0.21    --  107.75  76.00  31.00  184
  3  ω     96.00 176.00   0.50    0.21    --  107.75  30.00 120.00  160
  4  ω    146.00 174.00   0.50    0.21    --  107.75  45.00-120.00   56
  5  ω    139.00 176.00   0.50    0.21    --  107.75  15.00-180.00   74
  6  ω     96.00 135.00   0.50    0.21    --  107.75  15.00-180.00   78
  7  ω     42.00  69.00   0.50    0.21    --  107.75 -94.00   0.00   54
  8  ω     46.00  91.00   0.50    0.21    --  107.75-111.00  90.00   90
  9  ω     65.00  92.00   0.50    0.21    --  107.75-111.00 120.00   54
 10  ω     36.00 101.00   0.50    0.21    --  107.75 -94.00  90.00  130
 11  ω     32.00 104.00   0.50    0.21    --  107.75 -94.00 -90.00  144
 12  ω     32.00  69.00   0.50    0.21    --  107.75 -94.00-180.00   74
 13  ω     29.00  58.00   0.50    0.21    --  107.75 -15.00-120.00   58
 14  ω    -22.00  73.00   0.50    0.10    --   51.04 -76.00 -94.00  190
 15  ω     35.00 130.00   0.50    0.21    --  107.75 -76.00 -94.00  190
 16  ω     34.00 120.00   0.50    0.21    --  107.75 -30.00 -90.00  172
 17  ω     74.00 115.00   0.50    0.21    --  107.75 -15.00-120.00   82
 18  ω    118.00 178.00   0.50    0.21    --  107.75 111.00-120.00  120
 19  ω    104.00 145.00   0.50    0.21    --  107.75 178.00 -90.00   82
 20  ω    -73.00  22.00   0.50    0.10    --  -51.04  76.00  31.00  190
 21  ω    -83.00 -12.00   0.50    0.10    --  -51.04 125.00 120.00  142
 22  ω   -108.00 -13.00   0.50    0.21    --  -86.25  76.00  31.00  190
 23  ω   -126.00 -73.00   0.50    0.10    --  -51.04-125.00   0.00  106
 24  ω   -126.00 -73.00   0.50    0.10    --  -51.04-125.00 -60.00  106
 25  ω   -126.00 -73.00   0.50    0.10    --  -51.04-125.00-180.00  106
 26  ω   -159.00 -64.00   0.50    0.21    --  -86.25 -76.00 -94.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1379261000
_diffrn_orient_matrix_UB_12      -0.0018989000
_diffrn_orient_matrix_UB_13      -0.0497794000
_diffrn_orient_matrix_UB_21      -0.0582191000
_diffrn_orient_matrix_UB_22      -0.1089874000
_diffrn_orient_matrix_UB_23      0.0310176000
_diffrn_orient_matrix_UB_31      -0.0772282000
_diffrn_orient_matrix_UB_32      0.0850608000
_diffrn_orient_matrix_UB_33      0.0386779000
_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  0.0293
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_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       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10677
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.397
_diffrn_reflns_theta_min         4.033
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    21.174
_exptl_absorpt_correction_T_max  0.423
_exptl_absorpt_correction_T_min  0.097
_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    2.483
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.911
_refine_diff_density_min         -1.486
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       0.000040(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0246
_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/[σ²(Fo²)+(0.0338P)²+16.7274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0645
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2223
_reflns_number_total             2298
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           15
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_original_cell_volume        2270.72(10)
_cod_database_code               1568101
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.417
_shelx_estimated_absorpt_t_min   0.101
_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
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4530(5) 0.5722(5) 0.6691(2) 0.0273(10) Uani 1 1 d . . . . .
C2 C 0.6028(5) 0.3811(4) 0.7147(2) 0.0245(9) Uani 1 1 d . . . . .
C3 C 0.3325(5) 0.3897(4) 0.7240(2) 0.0214(9) Uani 1 1 d . . . . .
C4 C 0.4657(5) 0.1187(4) 0.6554(2) 0.0239(9) Uani 1 1 d . . . . .
H4 H 0.551460 0.131772 0.684844 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4261(5) 0.0036(4) 0.6392(2) 0.0243(9) Uani 1 1 d . . . . .
H5 H 0.485309 -0.061131 0.656926 0.029 Uiso 1 1 calc R U . . .
C6 C 0.2988(5) -0.0204(4) 0.5967(2) 0.0244(9) Uani 1 1 d . . . . .
C7 C 0.2187(5) 0.0789(4) 0.5719(2) 0.0239(9) Uani 1 1 d . . . . .
H7 H 0.131765 0.068137 0.542885 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2660(5) 0.1933(4) 0.58962(19) 0.0222(8) Uani 1 1 d . . . . .
C9 C 0.1841(5) 0.3032(4) 0.56334(19) 0.0228(8) Uani 1 1 d . . . . .
C10 C 0.2523(6) -0.1466(4) 0.5799(2) 0.0301(10) Uani 1 1 d . . . . .
H10A H 0.327033 -0.185991 0.560730 0.045 Uiso 1 1 calc R U . . .
H10B H 0.159341 -0.145501 0.551218 0.045 Uiso 1 1 calc R U . . .
H10C H 0.240117 -0.190822 0.616697 0.045 Uiso 1 1 calc R U . . .
N1 N 0.3874(4) 0.2150(3) 0.63107(16) 0.0211(7) Uani 1 1 d . . . . .
O1 O 0.4693(4) 0.6725(3) 0.67729(18) 0.0371(8) Uani 1 1 d . . . . .
O2 O 0.7037(4) 0.3679(3) 0.75191(16) 0.0296(7) Uani 1 1 d . . . . .
O3 O 0.2791(4) 0.3795(3) 0.76626(16) 0.0303(7) Uani 1 1 d . . . . .
O4 O 0.5439(4) 0.4059(3) 0.57776(17) 0.0288(8) Uani 1 1 d . . . . .
H4A H 0.506(7) 0.382(5) 0.548(3) 0.028(16) Uiso 1 1 d . . . . .
H4B H 0.590(7) 0.461(6) 0.570(3) 0.035(17) Uiso 1 1 d . . . . .
O5 O 0.0751(4) 0.2922(3) 0.52373(15) 0.0299(7) Uani 1 1 d . . . . .
O6 O 0.2363(4) 0.4048(3) 0.58531(15) 0.0247(7) Uani 1 1 d . . . . .
Re1 Re 0.42964(2) 0.40173(2) 0.65575(2) 0.02019(10) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 5 0.0175
1 0 -5 0.0365
-1 -1 -1 0.0939
1 1 1 0.0939
-4 5 0 0.0545
0 0 1 0.0282
5 -4 2 0.0668
-2 -1 -5 0.0744
1 -3 -5 0.0611
2 -5 2 0.0481
1 0 5 0.0558
-1 0 -5 0.0623
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 Re1 178.8(4) . . ?
O2 C2 Re1 177.2(4) . . ?
O3 C3 Re1 177.0(4) . . ?
C5 C4 H4 118.8 . . ?
N1 C4 H4 118.8 . . ?
N1 C4 C5 122.5(4) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(4) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C10 121.2(4) . . ?
C7 C6 C5 116.4(4) . . ?
C7 C6 C10 122.4(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 119.9(4) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 121.7(4) . . ?
N1 C8 C7 123.1(4) . . ?
N1 C8 C9 115.2(4) . . ?
O5 C9 C8 119.7(4) . . ?
O5 C9 O6 124.5(4) . . ?
O6 C9 C8 115.8(4) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 N1 Re1 126.7(3) . . ?
C8 N1 C4 117.3(4) . . ?
C8 N1 Re1 116.0(3) . . ?
H4A O4 H4B 106(6) . . ?
Re1 O4 H4A 118(5) . . ?
Re1 O4 H4B 124(5) . . ?
C9 O6 Re1 117.9(3) . . ?
C1 Re1 N1 173.54(17) . . ?
C1 Re1 O4 92.55(17) . . ?
C1 Re1 O6 98.79(16) . . ?
C2 Re1 C1 87.3(2) . . ?
C2 Re1 N1 98.76(16) . . ?
C2 Re1 O4 94.61(17) . . ?
C2 Re1 O6 173.55(16) . . ?
C3 Re1 C1 90.13(19) . . ?
C3 Re1 C2 84.45(19) . . ?
C3 Re1 N1 92.55(16) . . ?
C3 Re1 O4 177.12(16) . . ?
C3 Re1 O6 97.47(16) . . ?
N1 Re1 O4 84.89(14) . . ?
O6 Re1 N1 75.04(12) . . ?
O6 Re1 O4 83.18(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.138(6) . ?
C1 Re1 1.930(5) . ?
C2 O2 1.147(6) . ?
C2 Re1 1.904(5) . ?
C3 O3 1.144(6) . ?
C3 Re1 1.903(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.366(7) . ?
C4 N1 1.355(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.405(6) . ?
C6 C7 1.393(7) . ?
C6 C10 1.500(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(6) . ?
C8 C9 1.505(6) . ?
C8 N1 1.349(6) . ?
C9 O5 1.227(5) . ?
C9 O6 1.294(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N1 Re1 2.171(4) . ?
O4 H4A 0.74(7) . ?
O4 H4B 0.78(7) . ?
O4 Re1 2.189(4) . ?
O6 Re1 2.168(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4A O5 0.74(7) 1.92(7) 2.657(5) 169(7) 2_556 yes
O4 H4B O6 0.78(7) 2.01(7) 2.752(5) 157(6) 6_665 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C5 C6 C7 1.0(6) . . . . ?
C4 C5 C6 C10 -178.3(4) . . . . ?
C5 C4 N1 C8 0.3(6) . . . . ?
C5 C4 N1 Re1 176.4(3) . . . . ?
C5 C6 C7 C8 -0.1(6) . . . . ?
C6 C7 C8 C9 179.0(4) . . . . ?
C6 C7 C8 N1 -0.8(7) . . . . ?
C7 C8 C9 O5 -2.3(6) . . . . ?
C7 C8 C9 O6 177.5(4) . . . . ?
C7 C8 N1 C4 0.7(6) . . . . ?
C7 C8 N1 Re1 -175.8(3) . . . . ?
C8 C9 O6 Re1 -0.3(5) . . . . ?
C9 C8 N1 C4 -179.2(4) . . . . ?
C9 C8 N1 Re1 4.3(5) . . . . ?
C10 C6 C7 C8 179.2(4) . . . . ?
N1 C4 C5 C6 -1.1(7) . . . . ?
N1 C8 C9 O5 177.5(4) . . . . ?
N1 C8 C9 O6 -2.7(5) . . . . ?
O5 C9 O6 Re1 179.5(3) . . . . ?
