#------------------------------------------------------------------------------
#$Date: 2025-05-14 13:17:04 +0300 (Wed, 14 May 2025) $
#$Revision: 299663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/81/1568108.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_1568108
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 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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     87.00 177.00   0.50    0.20    --  107.75  77.00 -73.81  180
  2  ω    137.00 178.00   0.50    0.20    --  107.75  45.00 -60.00   82
  3  ω     96.00 132.00   0.50    0.20    --  107.75  45.00 -60.00   72
  4  ω     95.00 178.00   0.50    0.20    --  107.75  45.00 -90.00  166
  5  ω     94.00 169.00   0.50    0.20    --  107.75  30.00-120.00  150
  6  ω     92.00 151.00   0.50    0.20    --  107.75  61.00-180.00  118
  7  ω     32.00  87.00   0.50    0.20    --  107.75 -94.00-120.00  110
  8  ω     32.00 110.00   0.50    0.20    --  107.75-119.00-144.00  156
  9  ω     30.00  96.00   0.50    0.10    --   51.79-119.00-144.00  132
 10  ω     50.00 120.00   0.50    0.10    --   51.79-157.00  60.00  140
 11  ω     50.00 134.00   0.50    0.20    --  107.75-157.00  60.00  168
 12  ω     48.00  75.00   0.50    0.20    --  107.75-111.00 120.00   54
 13  ω     31.00 109.00   0.50    0.20    --  107.75-111.00 150.00  156
 14  ω     78.00 109.00   0.50    0.20    --  107.75-111.00  90.00   62
 15  ω     31.00  73.00   0.50    0.20    --  107.75-111.00  90.00   84
 16  ω     33.00 109.00   0.50    0.20    --  107.75-111.00  60.00  152
 17  ω     42.00  75.00   0.50    0.20    --  107.75-111.00   0.00   66
 18  ω     79.00 109.00   0.50    0.20    --  107.75-111.00   0.00   60
 19  ω     42.00 105.00   0.50    0.20    --  107.75-111.00 -60.00  126
 20  ω     32.00  71.00   0.50    0.20    --  107.75-111.00-120.00   78
 21  ω     76.00 109.00   0.50    0.20    --  107.75-111.00-120.00   66
 22  ω     48.00 108.00   0.50    0.20    --  107.75-111.00-180.00  120
 23  ω     29.00 112.00   0.50    0.20    --  107.75 -15.00 -60.00  166
 24  ω     37.00 124.00   0.50    0.20    --  107.75 -61.00-150.00  174
 25  ω     38.00 110.00   0.50    0.20    --  107.75 -61.00 -60.00  144
 26  ω     50.00 124.00   0.50    0.20    --  107.75 -61.00   0.00  148
 27  ω    100.00 126.00   0.50    0.20    --  107.75 -77.00 120.00   52
 28  ω     55.00  81.00   0.50    0.20    --  107.75 -77.00 120.00   52
 29  ω     30.00  96.00   0.50    0.20    --  107.75 -15.00  30.00  132
 30  ω    128.00 164.00   0.50    0.20    --  107.75 111.00-120.00   72
 31  ω     98.00 178.00   0.50    0.20    --  107.75 119.00 -58.00  160
 32  ω     72.00 126.00   0.50    0.10    --   51.79 157.00  96.00  108
 33  ω     72.00 161.00   0.50    0.20    --  107.75 157.00  96.00  178
 34  ω    -99.00 -10.00   0.50    0.20    --  -86.25  45.00 -30.00  178
 35  ω   -109.00 -28.00   0.50    0.10    --  -51.79 157.00  96.00  162
 36  ω    -84.00  -8.00   0.50    0.10    --  -51.79 119.00 -58.00  152
 37  ω    -85.00 -10.00   0.50    0.20    --  -86.25 119.00 -58.00  150
 38  ω   -124.00 -37.00   0.50    0.10    --  -51.79 -57.00-120.00  174
 39  ω   -125.00 -29.00   0.50    0.10    --  -51.79 -77.00   0.00  192
 40  ω   -125.00 -29.00   0.50    0.10    --  -51.79 -77.00 150.00  192
 41  ω   -144.00 -51.00   0.50    0.20    --  -86.25-157.00  60.00  186
 42  ω   -126.00 -51.00   0.50    0.10    --  -51.79-157.00  60.00  150
 43  ω   -162.00 -76.00   0.50    0.20    --  -86.25-119.00-144.00  172
 44  ω   -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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0261P)²+3.0030P] where P=(Fo²+2Fc²)/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 > 2σ(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_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   0.233
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.7334(5) 0.5270(4) 0.4974(3) 0.0247(8) Uani 1 1 d . . . . .
C2 C 0.6629(4) 0.3575(4) 0.6073(4) 0.0236(8) Uani 1 1 d . . . . .
C3 C 0.5456(5) 0.2706(4) 0.3797(4) 0.0240(8) Uani 1 1 d . . . . .
C4 C 0.7204(4) 0.0533(4) 0.5085(3) 0.0201(7) Uani 1 1 d . . . . .
H4 H 0.668829 0.078223 0.559418 0.024 Uiso 1 1 calc R U . . .
C5 C 0.7406(5) -0.0760(4) 0.4835(4) 0.0250(8) Uani 1 1 d . . . . .
H5 H 0.702089 -0.139374 0.516229 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8172(5) -0.1115(4) 0.4107(4) 0.0240(8) Uani 1 1 d . . . . .
H6 H 0.831670 -0.199575 0.392921 0.029 Uiso 1 1 calc R U . . .
C7 C 0.8730(4) -0.0177(4) 0.3635(3) 0.0204(7) Uani 1 1 d . . . . .
C8 C 0.8467(4) 0.1098(4) 0.3907(3) 0.0160(7) Uani 1 1 d . . . . .
C9 C 0.8980(4) 0.2150(4) 0.3420(3) 0.0171(7) Uani 1 1 d . . . . .
C10 C 0.8726(5) 0.0943(4) -0.0844(4) 0.0270(9) Uani 1 1 d . . . . .
C11 C 0.7024(4) 0.0663(4) 0.0373(4) 0.0256(8) Uani 1 1 d . . . . .
H4A H 1.019(5) 0.4980(14) 0.632(4) 0.031 Uiso 1 1 d D U . . .
H4B H 0.986(6) 0.395(5) 0.664(3) 0.031 Uiso 1 1 d D U . . .
H7 H 0.969(6) 0.010(4) 0.269(4) 0.031 Uiso 1 1 d D U . . .
H11A H 0.990(6) 0.302(5) 0.183(4) 0.031 Uiso 1 1 d D U . . .
H11B H 1.034(4) 0.365(5) 0.120(5) 0.031 Uiso 1 1 d D U . . .
H14A H 0.740(5) 0.701(6) 0.037(3) 0.031 Uiso 1 1 d D U . . .
H15A H 0.984(6) 0.235(4) -0.234(5) 0.038 Uiso 1 1 d D U . . .
H15B H 0.924(6) 0.326(6) -0.191(4) 0.038 Uiso 1 1 d D U . . .
C12 C 0.5995(5) 0.1123(4) -0.1589(4) 0.0281(9) Uani 1 1 d . . . . .
C13 C 0.5954(4) 0.3403(4) 0.1314(4) 0.0237(8) Uani 1 1 d . . . . .
H13 H 0.568614 0.253626 0.141273 0.028 Uiso 1 1 calc R U . . .
C14 C 0.5511(4) 0.4478(5) 0.1872(4) 0.0253(8) Uani 1 1 d . . . . .
H14 H 0.495008 0.433825 0.234797 0.030 Uiso 1 1 calc R U . . .
C15 C 0.5874(5) 0.5731(5) 0.1741(3) 0.0255(8) Uani 1 1 d . . . . .
H15 H 0.557637 0.646661 0.212410 0.031 Uiso 1 1 calc R U . . .
C16 C 0.6694(4) 0.5911(4) 0.1030(3) 0.0214(8) Uani 1 1 d . . . . .
C17 C 0.7112(4) 0.4791(4) 0.0486(3) 0.0177(7) Uani 1 1 d . . . . .
C18 C 0.7986(4) 0.4884(4) -0.0278(3) 0.0194(7) Uani 1 1 d . . . . .
N1 N 0.7723(3) 0.1436(3) 0.4621(3) 0.0157(6) Uani 1 1 d . . . . .
N2 N 0.6751(3) 0.3569(3) 0.0640(3) 0.0172(6) Uani 1 1 d . . . . .
O1 O 0.7204(4) 0.6328(3) 0.4985(3) 0.0384(8) Uani 1 1 d . . . . .
O2 O 0.6141(4) 0.3600(4) 0.6788(3) 0.0382(8) Uani 1 1 d . . . . .
O3 O 0.4259(4) 0.2252(4) 0.3151(3) 0.0388(8) Uani 1 1 d . . . . .
O4 O 0.9767(3) 0.4133(3) 0.6049(2) 0.0192(5) Uani 1 1 d D . . . .
O5 O 0.9727(3) 0.1930(3) 0.2789(2) 0.0222(5) Uani 1 1 d . . . . .
O6 O 0.8581(3) 0.3240(3) 0.3661(2) 0.0189(5) Uani 1 1 d . . . . .
O7 O 0.9504(3) -0.0513(3) 0.2949(3) 0.0258(6) Uani 1 1 d D . . . .
O8 O 0.9333(5) 0.0241(4) -0.1224(4) 0.0484(10) Uani 1 1 d . . . . .
O9 O 0.6579(4) -0.0188(4) 0.0700(3) 0.0416(8) Uani 1 1 d . . . . .
O10 O 0.5014(4) 0.0577(4) -0.2441(3) 0.0453(9) Uani 1 1 d . . . . .
O11 O 0.9621(3) 0.3400(3) 0.1381(2) 0.0203(5) Uani 1 1 d D . . . .
O12 O 0.8279(3) 0.5970(3) -0.0509(3) 0.0242(6) Uani 1 1 d . . . . .
O13 O 0.8385(3) 0.3837(3) -0.0665(2) 0.0199(5) Uani 1 1 d . . . . .
O14 O 0.7019(3) 0.7119(3) 0.0871(3) 0.0293(6) Uani 1 1 d D . . . .
O15 O 0.9641(4) 0.3045(3) -0.2380(3) 0.0297(6) Uani 1 1 d D . . . .
Re1 Re 0.74502(2) 0.34642(2) 0.48805(2) 0.01597(7) Uani 1 1 d . . . . .
Re2 Re 0.76832(2) 0.20794(2) -0.01892(2) 0.01687(7) 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 -2 5 0.0606
-3 5 0 0.0606
-1 0 0 0.0406
-2 5 -5 0.0706
5 -2 1 0.0514
5 2 1 0.0527
1 1 -1 0.0639
5 -2 -2 0.0650
2 -5 0 0.0857
1 4 -5 0.0619
5 -4 -4 0.0652
1 -3 -5 0.0532
-3 1 5 0.0896
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 176.8(4) . . ?
O2 C2 Re1 177.7(4) . . ?
O3 C3 Re1 179.7(4) . . ?
C5 C4 H4 119.4 . . ?
N1 C4 H4 119.4 . . ?
N1 C4 C5 121.3(4) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.3(4) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.7(4) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 118.1(4) . . ?
O7 C7 C6 119.5(3) . . ?
O7 C7 C8 122.5(4) . . ?
C7 C8 C9 122.1(3) . . ?
N1 C8 C7 121.8(3) . . ?
N1 C8 C9 116.1(3) . . ?
O5 C9 C8 119.6(3) . . ?
O5 C9 O6 123.7(3) . . ?
O6 C9 C8 116.6(3) . . ?
O8 C10 Re2 178.3(4) . . ?
O9 C11 Re2 177.7(4) . . ?
O10 C12 Re2 177.7(4) . . ?
C14 C13 H13 119.4 . . ?
N2 C13 H13 119.4 . . ?
N2 C13 C14 121.2(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.7 . . ?
C14 C15 C16 118.6(4) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C17 118.4(4) . . ?
O14 C16 C15 119.1(4) . . ?
O14 C16 C17 122.5(4) . . ?
C16 C17 C18 122.3(3) . . ?
N2 C17 C16 121.7(3) . . ?
N2 C17 C18 115.9(3) . . ?
O12 C18 C17 118.7(3) . . ?
O12 C18 O13 124.3(4) . . ?
O13 C18 C17 117.0(3) . . ?
C4 N1 C8 119.8(3) . . ?
C4 N1 Re1 126.0(3) . . ?
C8 N1 Re1 114.2(2) . . ?
C13 N2 C17 119.4(3) . . ?
C13 N2 Re2 126.5(3) . . ?
C17 N2 Re2 114.0(2) . . ?
H4A O4 H4B 103(5) . . ?
Re1 O4 H4A 114(4) . . ?
Re1 O4 H4B 113(4) . . ?
C9 O6 Re1 116.7(2) . . ?
C7 O7 H7 109(4) . . ?
H11A O11 H11B 104(5) . . ?
Re2 O11 H11A 116(4) . . ?
Re2 O11 H11B 109(4) . . ?
C18 O13 Re2 117.2(2) . . ?
C16 O14 H14A 106(4) . . ?
H15A O15 H15B 108(6) . . ?
C1 Re1 N1 172.79(15) . . ?
C1 Re1 O4 97.87(14) . . ?
C1 Re1 O6 96.88(14) . . ?
C2 Re1 C1 88.45(17) . . ?
C2 Re1 C3 87.16(17) . . ?
C2 Re1 N1 98.73(14) . . ?
C2 Re1 O4 95.19(14) . . ?
C2 Re1 O6 172.47(13) . . ?
C3 Re1 C1 87.39(17) . . ?
C3 Re1 N1 93.60(14) . . ?
C3 Re1 O4 174.29(13) . . ?
C3 Re1 O6 98.36(14) . . ?
N1 Re1 O4 80.90(11) . . ?
O6 Re1 N1 75.91(10) . . ?
O6 Re1 O4 78.85(10) . . ?
C10 Re2 N2 173.20(16) . . ?
C10 Re2 O11 94.27(15) . . ?
C10 Re2 O13 99.72(14) . . ?
C11 Re2 C10 86.24(18) . . ?
C11 Re2 C12 89.43(18) . . ?
C11 Re2 N2 98.04(15) . . ?
C11 Re2 O11 96.48(14) . . ?
C11 Re2 O13 173.46(15) . . ?
C12 Re2 C10 89.08(19) . . ?
C12 Re2 N2 96.21(15) . . ?
C12 Re2 O11 173.37(14) . . ?
C12 Re2 O13 93.34(15) . . ?
N2 Re2 O11 80.04(11) . . ?
O13 Re2 N2 75.78(11) . . ?
O13 Re2 O11 80.47(10) . . ?
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 1.154(5) . ?
C1 Re1 1.914(4) . ?
C2 O2 1.145(5) . ?
C2 Re1 1.908(4) . ?
C3 O3 1.145(5) . ?
C3 Re1 1.909(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(5) . ?
C4 N1 1.342(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(6) . ?
C7 C8 1.398(5) . ?
C7 O7 1.343(5) . ?
C8 C9 1.484(5) . ?
C8 N1 1.346(5) . ?
C9 O5 1.246(5) . ?
C9 O6 1.288(4) . ?
C10 O8 1.143(5) . ?
C10 Re2 1.920(4) . ?
C11 O9 1.147(6) . ?
C11 Re2 1.903(4) . ?
C12 O10 1.137(5) . ?
C12 Re2 1.907(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(6) . ?
C13 N2 1.339(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.364(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.399(6) . ?
C16 C17 1.406(5) . ?
C16 O14 1.334(5) . ?
C17 C18 1.483(5) . ?
C17 N2 1.348(5) . ?
C18 O12 1.259(5) . ?
C18 O13 1.276(5) . ?
N1 Re1 2.170(3) . ?
N2 Re2 2.173(3) . ?
O4 H4A 0.821(10) . ?
O4 H4B 0.821(10) . ?
O4 Re1 2.196(3) . ?
O6 Re1 2.150(3) . ?
O7 H7 0.820(10) . ?
O11 H11A 0.821(10) . ?
O11 H11B 0.819(10) . ?
O11 Re2 2.193(3) . ?
O13 Re2 2.147(3) . ?
O14 H14A 0.821(10) . ?
O15 H15A 0.817(10) . ?
O15 H15B 0.819(10) . ?
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
C5 H5 O1 0.95 2.41 3.110(5) 130.0 1_545 yes
O4 H4A O6 0.821(10) 1.99(3) 2.750(4) 155(5) 2_766 yes
O4 H4B O15 0.821(10) 1.816(19) 2.612(4) 163(5) 1_556 yes
O7 H7 O5 0.820(10) 1.90(3) 2.618(4) 146(5) . yes
O11 H11A O5 0.821(10) 1.92(2) 2.700(4) 158(5) . yes
O11 H11B O12 0.819(10) 1.848(15) 2.659(4) 170(5) 2_765 yes
O14 H14A O12 0.821(10) 1.88(3) 2.617(4) 150(5) . yes
O15 H15A O7 0.817(10) 2.19(3) 2.950(4) 155(6) 2_755 yes
O15 H15B O13 0.819(10) 2.014(12) 2.831(4) 176(6) . yes
C15 H15 O2 0.95 2.48 3.159(5) 128.7 2_666 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 0.0(6) . . . . ?
C5 C4 N1 C8 -0.6(6) . . . . ?
C5 C4 N1 Re1 178.1(3) . . . . ?
C5 C6 C7 C8 -1.1(6) . . . . ?
C5 C6 C7 O7 178.5(4) . . . . ?
C6 C7 C8 C9 -178.2(3) . . . . ?
C6 C7 C8 N1 1.3(6) . . . . ?
C7 C8 C9 O5 -3.3(5) . . . . ?
C7 C8 C9 O6 175.0(3) . . . . ?
C7 C8 N1 C4 -0.5(5) . . . . ?
C7 C8 N1 Re1 -179.4(3) . . . . ?
C8 C9 O6 Re1 6.6(4) . . . . ?
C9 C8 N1 C4 179.1(3) . . . . ?
C9 C8 N1 Re1 0.2(4) . . . . ?
C13 C14 C15 C16 0.3(6) . . . . ?
C14 C13 N2 C17 -1.0(6) . . . . ?
C14 C13 N2 Re2 175.0(3) . . . . ?
C14 C15 C16 C17 -0.3(6) . . . . ?
C14 C15 C16 O14 178.2(4) . . . . ?
C15 C16 C17 C18 -179.7(3) . . . . ?
C15 C16 C17 N2 -0.4(5) . . . . ?
C16 C17 C18 O12 -4.9(5) . . . . ?
C16 C17 C18 O13 175.6(3) . . . . ?
C16 C17 N2 C13 1.1(5) . . . . ?
C16 C17 N2 Re2 -175.4(3) . . . . ?
C17 C18 O13 Re2 1.5(4) . . . . ?
C18 C17 N2 C13 -179.6(3) . . . . ?
C18 C17 N2 Re2 3.9(4) . . . . ?
N1 C4 C5 C6 0.8(6) . . . . ?
N1 C8 C9 O5 177.1(3) . . . . ?
N1 C8 C9 O6 -4.6(5) . . . . ?
N2 C13 C14 C15 0.3(6) . . . . ?
N2 C17 C18 O12 175.8(3) . . . . ?
N2 C17 C18 O13 -3.7(5) . . . . ?
O5 C9 O6 Re1 -175.2(3) . . . . ?
O7 C7 C8 C9 2.2(6) . . . . ?
O7 C7 C8 N1 -178.2(3) . . . . ?
O12 C18 O13 Re2 -178.0(3) . . . . ?
O14 C16 C17 C18 1.9(6) . . . . ?
O14 C16 C17 N2 -178.8(3) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0046 -2.0038 4.9945 0.1094 0.6352 -0.2261
-2.9847 4.9996 -0.0046 0.1254 -0.0120 0.7869
-1.0007 -0.0008 0.0019 0.1392 -0.0951 0.0300
-1.9948 5.0042 -4.9988 -0.1455 -0.5662 0.6743
4.9988 -1.9977 0.9931 -0.5528 0.4961 -0.4122
5.0128 2.0038 0.9848 -0.7865 0.7149 0.1453
1.0020 1.0019 -1.0024 -0.2240 0.0199 0.0929
4.9923 -1.9954 -2.0023 -0.6318 0.1065 -0.4618
1.9839 -5.0003 0.0065 0.0138 -0.0832 -0.7569
1.0038 4.0061 -5.0024 -0.5046 -0.3355 0.4449
4.9809 -3.9946 -3.9950 -0.5676 -0.2626 -0.7736
0.9793 -2.9965 -4.9879 -0.0956 -0.7183 -0.5308
-2.9878 0.9943 4.9959 0.4908 0.4187 0.3120
