#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:04:58 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281396 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/80/1568097.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_1568097
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         'C9 H5 Cl N O6 Re'
_chemical_formula_sum            'C9 H5 Cl N O6 Re'
_chemical_formula_weight         444.79
_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             2021-04-12
_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                 99.6720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.33670(10)
_cell_length_b                   11.12590(10)
_cell_length_c                   22.2200(2)
_cell_measurement_reflns_used    11234
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      79.0280
_cell_measurement_theta_min      3.9950
_cell_volume                     2275.39(4)
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     92.00 178.00   0.50    1.20    --  107.75  61.00 -30.00  172
  2  ω     94.00 178.00   0.50    1.20    --  107.75  30.00   0.00  168
  3  ω     96.00 178.00   0.50    1.20    --  107.75  15.00 -30.00  164
  4  ω     91.00 178.00   0.50    1.20    --  107.75  64.00  45.00  174
  5  ω    129.00 178.00   0.50    1.20    --  107.75  15.00 150.00   98
  6  ω     96.00 178.00   0.50    1.20    --  107.75  15.00 120.00  164
  7  ω     96.00 178.00   0.50    1.20    --  107.75  15.00  90.00  164
  8  ω     85.00 178.00   0.50    1.20    --  107.75  77.00 120.00  186
  9  ω     32.00 120.00   0.50    1.20    --  107.75 -45.00  60.00  176
 10  ω    -18.00  69.00   0.50    0.30    --   51.79 -64.00 -90.00  174
 11  ω     38.00 125.00   0.50    1.20    --  107.75 -64.00 -90.00  174
 12  ω    102.00 178.00   0.50    1.20    --  107.75 111.00 -30.00  152
 13  ω     31.00 109.00   0.50    1.20    --  107.75-111.00  60.00  156
 14  ω     36.00 101.00   0.50    1.20    --  107.75 -94.00 120.00  130
 15  ω   -122.00 -35.00   0.50    0.30    --  -51.79 -64.00 -90.00  174
 16  ω   -126.00 -73.00   0.50    0.30    --  -51.79-125.00   0.00  106
 17  ω   -126.00 -73.00   0.50    0.30    --  -51.79-125.00  90.00  106
 18  ω    -69.00  18.00   0.50    0.30    --  -51.79  64.00  45.00  174
 19  ω   -103.00 -16.00   0.50    1.20    --  -86.25  64.00  45.00  174
;
_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      0.0647678000
_diffrn_orient_matrix_UB_12      -0.0953672000
_diffrn_orient_matrix_UB_13      -0.0379284000
_diffrn_orient_matrix_UB_21      -0.1049369000
_diffrn_orient_matrix_UB_22      0.0401900000
_diffrn_orient_matrix_UB_23      -0.0575511000
_diffrn_orient_matrix_UB_31      0.1132209000
_diffrn_orient_matrix_UB_32      0.0918837000
_diffrn_orient_matrix_UB_33      -0.0141372000
_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  0.0163
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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            11613
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.487
_diffrn_reflns_theta_min         4.036
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    23.293
_exptl_absorpt_correction_T_max  0.467
_exptl_absorpt_correction_T_min  0.200
_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    2.597
_exptl_crystal_description       plate
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.000335(8)
_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   1.289
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.289
_refine_ls_R_factor_all          0.0136
_refine_ls_R_factor_gt           0.0134
_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/[σ²(Fo²)+(0.0136P)²+4.7286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0330
_refine_ls_wR_factor_ref         0.0336
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2309
_reflns_number_total             2318
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           13
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_database_code               1568097
_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   0.456
_shelx_estimated_absorpt_t_min   0.184
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
;
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 0.5396(3) 0.5734(2) 0.32957(12) 0.0217(5) Uani 1 1 d . . . . .
C2 C 0.3911(3) 0.3810(2) 0.28507(12) 0.0178(5) Uani 1 1 d . . . . .
C3 C 0.6609(3) 0.3904(2) 0.27475(12) 0.0177(5) Uani 1 1 d . . . . .
C4 C 0.5375(3) 0.1187(2) 0.34463(11) 0.0183(5) Uani 1 1 d . . . . .
H4 H 0.451456 0.130139 0.315631 0.022 Uiso 1 1 calc R U . . .
C5 C 0.5811(3) 0.0026(2) 0.36064(12) 0.0196(5) Uani 1 1 d . . . . .
H5 H 0.525929 -0.064404 0.343314 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7080(3) -0.0136(2) 0.40284(11) 0.0204(5) Uani 1 1 d . . . . .
C7 C 0.7853(3) 0.0854(2) 0.42818(12) 0.0195(5) Uani 1 1 d . . . . .
H7 H 0.871665 0.076246 0.457236 0.023 Uiso 1 1 calc R U . . .
C8 C 0.7326(3) 0.1986(2) 0.40983(11) 0.0165(4) Uani 1 1 d . . . . .
C9 C 0.8102(3) 0.3110(2) 0.43584(11) 0.0181(5) Uani 1 1 d . . . . .
Cl1 Cl 0.76971(8) -0.15628(6) 0.42250(3) 0.02915(14) Uani 1 1 d . . . . .
N1 N 0.6116(2) 0.21601(18) 0.36837(9) 0.0152(4) Uani 1 1 d . . . . .
O1 O 0.5231(2) 0.67430(17) 0.32121(10) 0.0307(4) Uani 1 1 d . . . . .
O2 O 0.2901(2) 0.36872(17) 0.24841(9) 0.0254(4) Uani 1 1 d . . . . .
O3 O 0.7121(2) 0.38000(18) 0.23123(9) 0.0252(4) Uani 1 1 d . . . . .
O4 O 0.4516(2) 0.40407(17) 0.42175(9) 0.0205(4) Uani 1 1 d . . . . .
H4A H 0.493(4) 0.381(3) 0.455(2) 0.032(10) Uiso 1 1 d . . . . .
H4B H 0.401(4) 0.455(4) 0.4240(17) 0.030(10) Uiso 1 1 d . . . . .
O5 O 0.91660(19) 0.30113(17) 0.47621(9) 0.0246(4) Uani 1 1 d . . . . .
O6 O 0.75570(19) 0.41045(15) 0.41283(8) 0.0186(4) Uani 1 1 d . . . . .
Re1 Re 0.56429(2) 0.40289(2) 0.34294(2) 0.01436(5) 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'
Cl Cl 0.3639 0.7018 '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 -1 0 0.0209
-1 1 0 0.0209
0 0 -1 0.0360
0 0 1 0.0360
1 1 0 0.0526
-1 -1 0 0.0426
-1 1 5 0.0353
-1 1 -5 0.0306
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 179.1(3) . . ?
O2 C2 Re1 177.2(2) . . ?
O3 C3 Re1 175.9(2) . . ?
C5 C4 H4 118.6 . . ?
N1 C4 H4 118.6 . . ?
N1 C4 C5 122.8(2) . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.3(2) . . ?
C6 C5 H5 120.8 . . ?
C5 C6 Cl1 120.1(2) . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 Cl1 120.1(2) . . ?
C6 C7 H7 121.0 . . ?
C6 C7 C8 117.9(2) . . ?
C8 C7 H7 121.0 . . ?
C7 C8 C9 121.0(2) . . ?
N1 C8 C7 123.1(2) . . ?
N1 C8 C9 115.9(2) . . ?
O5 C9 C8 118.9(2) . . ?
O5 C9 O6 125.8(2) . . ?
O6 C9 C8 115.3(2) . . ?
C4 N1 C8 118.1(2) . . ?
C4 N1 Re1 126.71(17) . . ?
C8 N1 Re1 115.12(16) . . ?
H4A O4 H4B 113(4) . . ?
Re1 O4 H4A 120(3) . . ?
Re1 O4 H4B 117(3) . . ?
C9 O6 Re1 118.37(15) . . ?
C1 Re1 N1 172.76(9) . . ?
C1 Re1 O4 93.22(9) . . ?
C1 Re1 O6 97.78(9) . . ?
C2 Re1 C1 87.48(11) . . ?
C2 Re1 N1 99.49(9) . . ?
C2 Re1 O4 94.20(9) . . ?
C2 Re1 O6 174.09(8) . . ?
C3 Re1 C1 90.55(11) . . ?
C3 Re1 C2 85.11(11) . . ?
C3 Re1 N1 91.96(9) . . ?
C3 Re1 O4 176.13(9) . . ?
C3 Re1 O6 97.48(9) . . ?
N1 Re1 O4 84.39(7) . . ?
O6 Re1 N1 75.17(7) . . ?
O6 Re1 O4 82.85(7) . . ?
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 1.144(3) . ?
C1 Re1 1.928(3) . ?
C2 O2 1.146(3) . ?
C2 Re1 1.905(3) . ?
C3 O3 1.155(3) . ?
C3 Re1 1.894(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(4) . ?
C4 N1 1.345(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(4) . ?
C6 C7 1.384(4) . ?
C6 Cl1 1.720(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(3) . ?
C8 C9 1.510(3) . ?
C8 N1 1.346(3) . ?
C9 O5 1.227(3) . ?
C9 O6 1.287(3) . ?
N1 Re1 2.180(2) . ?
O4 H4A 0.81(4) . ?
O4 H4B 0.75(4) . ?
O4 Re1 2.1890(19) . ?
O6 Re1 2.1633(18) . ?
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 0.81(4) 1.85(4) 2.651(3) 170(4) 2_656 yes
O4 H4B O6 0.75(4) 2.01(4) 2.743(3) 169(4) 6_565 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(4) . . . . ?
C4 C5 C6 Cl1 -178.06(19) . . . . ?
C5 C4 N1 C8 -0.6(4) . . . . ?
C5 C4 N1 Re1 175.50(18) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 C9 179.5(2) . . . . ?
C6 C7 C8 N1 -0.7(4) . . . . ?
C7 C8 C9 O5 -4.0(3) . . . . ?
C7 C8 C9 O6 176.3(2) . . . . ?
C7 C8 N1 C4 1.2(3) . . . . ?
C7 C8 N1 Re1 -175.32(18) . . . . ?
C8 C9 O6 Re1 0.8(3) . . . . ?
C9 C8 N1 C4 -178.9(2) . . . . ?
C9 C8 N1 Re1 4.5(3) . . . . ?
Cl1 C6 C7 C8 178.63(18) . . . . ?
N1 C4 C5 C6 -0.5(4) . . . . ?
N1 C8 C9 O5 176.1(2) . . . . ?
N1 C8 C9 O6 -3.6(3) . . . . ?
O5 C9 O6 Re1 -178.87(19) . . . . ?
