#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:04:58 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281396 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/81/1568116.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_1568116
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, H2 O'
_chemical_formula_sum            'C10 H10 N O7 Re'
_chemical_formula_weight         442.39
_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             2021-03-15
_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                 97.9890(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.18810(10)
_cell_length_b                   11.06790(10)
_cell_length_c                   25.0097(3)
_cell_measurement_reflns_used    12874
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      79.1620
_cell_measurement_theta_min      3.5700
_cell_volume                     2518.63(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 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    102.00 178.00   0.50    0.20    --  110.00 111.00  90.00  152
  2  ω     96.00 178.00   0.50    0.20    --  110.00  30.00 -30.00  164
  3  ω     96.00 178.00   0.50    0.20    --  110.00  30.00 -60.00  164
  4  ω    106.00 178.00   0.50    0.20    --  110.00  98.00-128.00  144
  5  ω     34.00 123.00   0.50    0.10    --   49.87  57.00 -60.00  178
  6  ω    -81.00 -11.00   0.50    0.20    --  -88.50  98.00-128.00  140
  7  ω   -125.00 -73.00   0.50    0.10    --  -49.87-125.00 -90.00  104
  8  ω   -165.00 -85.00   0.50    0.20    --  -88.50 -98.00 124.00  160
  9  ω   -125.00 -73.00   0.50    0.10    --  -49.87-125.00-150.00  104
 10  ω    -80.00  28.00   0.50    0.10    --  -49.87  98.00-128.00  216
 11  ω     36.00 134.00   0.50    0.20    --  110.00 -77.00 -60.00  196
 12  ω     34.00 124.00   0.50    0.20    --  110.00 -45.00 -30.00  180
 13  ω     34.00 108.00   0.50    0.20    --  110.00-111.00 -60.00  148
 14  ω     34.00 107.00   0.50    0.20    --  110.00 -94.00 -60.00  146
 15  ω     34.00 108.00   0.50    0.20    --  110.00-111.00-150.00  148
 16  ω     34.00 107.00   0.50    0.20    --  110.00 -94.00-180.00  146
 17  ω     34.00 107.00   0.50    0.20    --  110.00 -94.00-120.00  146
 18  ω     -6.00  84.00   0.50    0.10    --   49.87 -98.00 124.00  180
 19  ω     34.00 107.00   0.50    0.20    --  110.00 -98.00 124.00  146
 20  ω     38.00 127.00   0.50    0.20    --  110.00 -61.00  60.00  178
;
_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      -0.0336750000
_diffrn_orient_matrix_UB_12      0.1310141000
_diffrn_orient_matrix_UB_13      -0.0185632000
_diffrn_orient_matrix_UB_21      -0.1460051000
_diffrn_orient_matrix_UB_22      -0.0049186000
_diffrn_orient_matrix_UB_23      0.0236743000
_diffrn_orient_matrix_UB_31      0.0788937000
_diffrn_orient_matrix_UB_32      0.0467339000
_diffrn_orient_matrix_UB_33      0.0544338000
_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     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       31
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13080
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.493
_diffrn_reflns_theta_min         3.569
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    19.187
_exptl_absorpt_correction_T_max  0.308
_exptl_absorpt_correction_T_min  0.038
_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    2.333
_exptl_crystal_description       prism
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.452
_refine_diff_density_min         -1.101
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       0.000159(11)
_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   1.203
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2565
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.202
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0222
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0268P)²+10.9719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0575
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2557
_reflns_number_total             2565
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc05473f2.cif
_cod_data_source_block           35
_cod_depositor_comments
'Adding full bibliography for 1568094--1568122.cif.'
_cod_database_code               1568116
_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   0.250
_shelx_estimated_absorpt_t_min   0.086
_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, All C(H,H,H,H) groups, All O(H) groups
2. Restrained distances
 O7-H7B \\sim O7-H7C
 with sigma of 0.005
3. Others
 Fixed Sof: H7B(0.5) H7C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
4.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
Re1 Re 0.38657(2) 0.81880(2) 0.63515(2) 0.02115(9) Uani 1 1 d . . . . .
O1 O 0.3891(4) 1.0947(3) 0.62927(14) 0.0482(9) Uani 1 1 d . . . . .
O2 O 0.6377(4) 0.8547(3) 0.72765(14) 0.0487(9) Uani 1 1 d . . . . .
O3 O 0.1719(4) 0.8468(4) 0.71679(15) 0.0500(9) Uani 1 1 d . . . . .
O4 O 0.5257(3) 0.7916(3) 0.57204(11) 0.0263(5) Uani 1 1 d . . . . .
O5 O 0.0793(3) 0.6641(2) 0.51527(11) 0.0260(6) Uani 1 1 d . . . . .
O6 O 0.2150(3) 0.7938(2) 0.56876(11) 0.0245(5) Uani 1 1 d . . . . .
N1 N 0.3652(3) 0.6187(3) 0.62495(12) 0.0198(6) Uani 1 1 d . . . . .
C1 C 0.3891(5) 0.9918(4) 0.63106(16) 0.0343(10) Uani 1 1 d . . . . .
C2 C 0.5457(5) 0.8385(4) 0.69269(17) 0.0324(9) Uani 1 1 d . . . . .
H4A H 0.497(6) 0.757(6) 0.545(3) 0.049 Uiso 1 1 d . U . . .
H4B H 0.563(7) 0.852(6) 0.559(3) 0.049 Uiso 1 1 d . U . . .
H7A H 0.153(6) 0.940(6) 0.541(2) 0.049 Uiso 1 1 d . U . . .
H7B H 0.219(9) 1.028(10) 0.515(4) 0.049 Uiso 0.5 1 d D U P A 1
C3 C 0.2543(5) 0.8351(4) 0.68655(17) 0.0317(9) Uani 1 1 d . . . . .
C4 C 0.4442(4) 0.5297(3) 0.65253(14) 0.0220(7) Uani 1 1 d . . . . .
C5 C 0.4187(4) 0.4086(4) 0.63833(15) 0.0269(8) Uani 1 1 d . . . . .
H5 H 0.476280 0.347384 0.657674 0.032 Uiso 1 1 calc R U . . .
C6 C 0.3112(4) 0.3769(3) 0.59671(18) 0.0302(8) Uani 1 1 d . . . . .
H6 H 0.294176 0.294500 0.587109 0.036 Uiso 1 1 calc R U . . .
C7 C 0.2282(4) 0.4682(3) 0.56906(15) 0.0255(7) Uani 1 1 d . . . . .
H7 H 0.152328 0.449729 0.540419 0.031 Uiso 1 1 calc R U . . .
C8 C 0.2588(4) 0.5858(3) 0.58421(14) 0.0214(7) Uani 1 1 d . . . . .
C9 C 0.1761(4) 0.6872(3) 0.55326(14) 0.0212(7) Uani 1 1 d . . . . .
C10 C 0.5625(4) 0.5621(4) 0.69765(16) 0.0290(8) Uani 1 1 d . . . . .
H10A H 0.636392 0.612534 0.683656 0.044 Uiso 1 1 calc R U . . .
H10B H 0.609105 0.488207 0.713387 0.044 Uiso 1 1 calc R U . . .
H10C H 0.519524 0.606831 0.725442 0.044 Uiso 1 1 calc R U . . .
O7 O 0.1336(3) 1.0127(3) 0.52944(12) 0.0308(6) Uani 1 1 d D . . . .
H7C H 0.061(9) 0.993(11) 0.502(4) 0.046 Uiso 0.5 1 d D U P B 2
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
0 0 1 0.0561
0 0 -1 0.0561
-1 -1 0 0.0904
1 1 0 0.0904
0 -1 0 0.0502
0 1 0 0.0502
1 0 0 0.1186
-1 0 0 0.1186
2 0 -5 0.0978
0 1 1 0.0464
0 -1 1 0.0504
-4 5 1 0.0950
4 -5 -1 0.0950
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
O4 Re1 N1 80.33(11) . . ?
O6 Re1 O4 82.17(11) . . ?
O6 Re1 N1 74.95(10) . . ?
C1 Re1 O4 94.96(15) . . ?
C1 Re1 O6 95.76(13) . . ?
C1 Re1 N1 170.01(14) . . ?
C2 Re1 O4 95.53(16) . . ?
C2 Re1 O6 177.62(15) . . ?
C2 Re1 N1 104.15(14) . . ?
C2 Re1 C1 84.99(17) . . ?
C3 Re1 O4 175.49(15) . . ?
C3 Re1 O6 93.77(15) . . ?
C3 Re1 N1 96.75(15) . . ?
C3 Re1 C1 87.39(18) . . ?
C3 Re1 C2 88.51(19) . . ?
Re1 O4 H4A 122(4) . . ?
Re1 O4 H4B 119(4) . . ?
H4A O4 H4B 99(6) . . ?
C9 O6 Re1 119.9(2) . . ?
C4 N1 Re1 129.1(2) . . ?
C4 N1 C8 117.7(3) . . ?
C8 N1 Re1 113.2(2) . . ?
O1 C1 Re1 178.9(4) . . ?
O2 C2 Re1 177.0(4) . . ?
O3 C3 Re1 178.3(4) . . ?
N1 C4 C5 120.6(3) . . ?
N1 C4 C10 119.4(3) . . ?
C5 C4 C10 120.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 120.8 . . ?
C5 C6 C7 118.4(4) . . ?
C7 C6 H6 120.8 . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.3(4) . . ?
C8 C7 H7 120.8 . . ?
N1 C8 C7 124.0(3) . . ?
N1 C8 C9 116.3(3) . . ?
C7 C8 C9 119.7(3) . . ?
O5 C9 O6 124.5(3) . . ?
O5 C9 C8 119.9(3) . . ?
O6 C9 C8 115.6(3) . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H7A O7 H7B 98(8) . . ?
H7A O7 H7C 97(8) . . ?
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
Re1 O4 2.185(3) . ?
Re1 O6 2.142(3) . ?
Re1 N1 2.234(3) . ?
Re1 C1 1.918(5) . ?
Re1 C2 1.916(4) . ?
Re1 C3 1.896(5) . ?
O1 C1 1.139(6) . ?
O2 C2 1.143(5) . ?
O3 C3 1.149(6) . ?
O4 H4A 0.80(7) . ?
O4 H4B 0.83(7) . ?
O5 C9 1.234(5) . ?
O6 C9 1.278(4) . ?
N1 C4 1.354(5) . ?
N1 C8 1.360(5) . ?
C4 C5 1.398(5) . ?
C4 C10 1.498(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.373(5) . ?
C8 C9 1.508(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O7 H7A 0.87(7) . ?
O7 H7B 0.92(7) . ?
O7 H7C 0.92(7) . ?
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 0.80(7) 1.87(7) 2.665(4) 174(6) 2_556 yes
O4 H4B O7 0.83(7) 1.83(7) 2.665(4) 176(6) 6_675 yes
O7 H7A O6 0.87(7) 1.82(7) 2.682(4) 173(6) . yes
O7 H7B O7 0.92(7) 1.88(8) 2.760(6) 160(10) 2_556 yes
C6 H6 O1 0.95 2.55 3.282(5) 133.8 1_545 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
Re1 O6 C9 O5 -179.5(3) . . . . ?
Re1 O6 C9 C8 -0.4(4) . . . . ?
Re1 N1 C4 C5 -176.9(3) . . . . ?
Re1 N1 C4 C10 1.5(5) . . . . ?
Re1 N1 C8 C7 177.8(3) . . . . ?
Re1 N1 C8 C9 0.5(4) . . . . ?
N1 C4 C5 C6 -1.1(6) . . . . ?
N1 C8 C9 O5 179.0(3) . . . . ?
N1 C8 C9 O6 -0.1(5) . . . . ?
C4 N1 C8 C7 -0.8(5) . . . . ?
C4 N1 C8 C9 -178.2(3) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?
C5 C6 C7 C8 0.8(6) . . . . ?
C6 C7 C8 N1 -0.3(6) . . . . ?
C6 C7 C8 C9 176.9(3) . . . . ?
C7 C8 C9 O5 1.5(5) . . . . ?
C7 C8 C9 O6 -177.6(3) . . . . ?
C8 N1 C4 C5 1.6(5) . . . . ?
C8 N1 C4 C10 179.9(3) . . . . ?
C10 C4 C5 C6 -179.5(4) . . . . ?
