#------------------------------------------------------------------------------
#$Date: 2025-05-14 13:17:04 +0300 (Wed, 14 May 2025) $
#$Revision: 299663 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/81/1568118.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_1568118
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 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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  27.00   0.80    1.00    --  -42.61  57.00-180.00  120
  2  ω    -74.00  30.00   0.80    1.00    --  -42.61  77.00 -60.00  130
  3  ω   -113.00 -17.00   0.80    1.00    --  -42.61 -57.00  30.00  120
  4  ω     10.00  42.00   0.80    1.00    --   42.61  81.00   4.31   40
  5  ω     11.00  40.60   0.80    1.00    --   42.61  77.00-145.88   37
  6  ω    -21.00  73.40   0.80    1.00    --   42.61 -77.00 -90.00  118
  7  ω     30.00 106.00   0.80    2.00    --  111.00 -94.00-150.00   95
  8  ω     41.00 138.60   0.80    2.00    --  111.00 -61.00 -60.00  122
  9  ω     36.00 108.00   0.80    2.00    --  111.00-111.00 120.00   90
 10  ω    104.00 177.60   0.80    2.00    --  111.00 111.00-120.00   92
 11  ω    104.00 177.60   0.80    2.00    --  111.00 111.00   0.00   92
 12  ω     36.00 108.00   0.80    2.00    --  111.00-111.00 -30.00   90
 13  ω     87.00 177.40   0.80    2.00    --  111.00  30.00-120.00  113
 14  ω     30.00 106.00   0.80    2.00    --  111.00 -94.00 -90.00   95
 15  ω     36.00 108.00   0.80    2.00    --  111.00-111.00-150.00   90
 16  ω     36.00 134.40   0.80    2.00    --  111.00 -30.00 -90.00  123
 17  ω     36.00 108.00   0.80    2.00    --  111.00-111.00  30.00   90
 18  ω     36.00 108.00   0.80    2.00    --  111.00-111.00  90.00   90
 19  ω    104.00 177.60   0.80    2.00    --  111.00 111.00 -90.00   92
 20  ω     36.00 134.40   0.80    2.00    --  111.00 -30.00-180.00  123
 21  ω     30.00 106.00   0.80    2.00    --  111.00 -94.00 150.00   95
 22  ω    103.00 177.40   0.80    2.00    --  111.00  77.00 120.00   93
 23  ω     87.00 177.40   0.80    2.00    --  111.00  45.00 -90.00  113
 24  ω     37.00 141.00   0.80    2.00    --  111.00 -77.00 -90.00  130
 25  ω    103.00 177.40   0.80    2.00    --  111.00  77.00  30.00   93
 26  ω     30.00 106.00   0.80    2.00    --  111.00 -94.00-120.00   95
 27  ω    104.00 177.60   0.80    2.00    --  111.00 111.00-150.00   92
 28  ω     87.00 177.40   0.80    2.00    --  111.00  30.00-180.00  113
 29  ω   -116.00 -20.00   0.80    1.00    --  -42.61 -37.00 -90.00  120
 30  ω   -113.00 -17.00   0.80    1.00    --  -42.61 -57.00 120.00  120
 31  ω    -65.00  29.40   0.80    1.00    --  -42.61  37.00  90.00  118
 32  ω     10.00  42.00   0.80    1.00    --   42.61  80.00  54.70   40
 33  ω     11.00  40.60   0.80    1.00    --   42.61  79.00-109.67   37
 34  ω     10.00  42.00   0.80    1.00    --   42.61  81.00 156.05   40
 35  ω     11.00  40.60   0.80    1.00    --   42.61  78.00 -67.33   37
 36  ω     83.00 177.40   0.80    2.00    --  111.00  64.00-172.63  118
 37  ω     83.00 177.40   0.80    2.00    --  111.00  61.00 120.00  118
 38  ω     83.00 177.40   0.80    2.00    --  111.00  61.00  30.00  118
 39  ω     83.00 177.40   0.80    2.00    --  111.00  61.00 -60.00  118
 40  ω     83.00 177.40   0.80    2.00    --  111.00  61.00  90.00  118
 41  ω     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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0358P)²+0.7159P] where P=(Fo²+2Fc²)/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 > 2σ(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_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   0.459
_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)
;
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 0.6253(3) 0.8902(3) 0.9655(3) 0.0203(6) Uani 1 1 d . . . . .
C2 C 0.5204(3) 0.6880(3) 0.7595(3) 0.0149(5) Uani 1 1 d . . . . .
C3 C 0.5773(3) 0.6457(3) 0.9589(2) 0.0170(5) Uani 1 1 d . . . . .
C4 C 0.2068(3) 0.4344(2) 0.6902(2) 0.0140(5) Uani 1 1 d . . . . .
H4 H 0.257415 0.447231 0.643695 0.017 Uiso 1 1 calc R U . . .
C5 C 0.0839(3) 0.3145(3) 0.6488(2) 0.0160(5) Uani 1 1 d . . . . .
C6 C 0.0070(3) 0.2936(3) 0.7150(2) 0.0165(5) Uani 1 1 d . . . . .
H6 H -0.076664 0.211718 0.688223 0.020 Uiso 1 1 calc R U . . .
C7 C 0.0569(3) 0.3966(3) 0.8214(2) 0.0157(5) Uani 1 1 d . . . . .
H7 H 0.007003 0.386614 0.868647 0.019 Uiso 1 1 calc R U . . .
C8 C 0.1799(3) 0.5137(2) 0.8579(2) 0.0108(4) Uani 1 1 d . . . . .
C9 C 0.2431(3) 0.6310(2) 0.9729(2) 0.0132(5) Uani 1 1 d . . . . .
C10 C 0.0419(3) 0.2143(3) 0.5354(3) 0.0242(6) Uani 1 1 d . . . . .
H4A H 0.349(4) 0.8680(13) 0.795(4) 0.036 Uiso 1 1 d D U . . .
H4B H 0.276(4) 0.754(4) 0.7078(12) 0.036 Uiso 1 1 d D U . . .
H10A H 0.671(4) 0.1374(12) 0.716(4) 0.036 Uiso 1 1 d D U . . .
H10B H 0.730(4) 0.255(4) 0.8012(13) 0.036 Uiso 1 1 d D U . . .
C11 C 0.3780(3) 0.0942(3) 0.5513(3) 0.0174(5) Uani 1 1 d . . . . .
C12 C 0.4722(3) 0.3020(3) 0.7397(3) 0.0157(5) Uani 1 1 d . . . . .
C13 C 0.4096(3) 0.3325(3) 0.5349(2) 0.0164(5) Uani 1 1 d . . . . .
C14 C 0.7858(3) 0.5598(3) 0.7991(2) 0.0143(5) Uani 1 1 d . . . . .
H14 H 0.735525 0.551391 0.846143 0.017 Uiso 1 1 calc R U . . .
C15 C 0.9105(3) 0.6764(2) 0.8376(2) 0.0156(5) Uani 1 1 d . . . . .
C16 C 0.9869(3) 0.6919(3) 0.7707(2) 0.0166(5) Uani 1 1 d . . . . .
H16 H 1.071822 0.772046 0.795901 0.020 Uiso 1 1 calc R U . . .
C17 C 0.9338(3) 0.5854(3) 0.6655(2) 0.0154(5) Uani 1 1 d . . . . .
H17 H 0.982933 0.591076 0.617504 0.019 Uiso 1 1 calc R U . . .
C18 C 0.8096(3) 0.4718(2) 0.6320(2) 0.0111(4) Uani 1 1 d . . . . .
C19 C 0.7441(3) 0.3508(2) 0.5192(2) 0.0122(4) Uani 1 1 d . . . . .
C20 C 0.9574(4) 0.7802(3) 0.9499(3) 0.0274(6) Uani 1 1 d . . . . .
N1 N 0.2559(2) 0.5324(2) 0.7940(2) 0.0110(4) Uani 1 1 d . . . . .
N2 N 0.0175(4) 0.1429(3) 0.4481(3) 0.0392(7) Uani 1 1 d . . . . .
N3 N 0.7344(2) 0.4586(2) 0.6970(2) 0.0109(4) Uani 1 1 d . . . . .
N4 N 0.9884(4) 0.8556(3) 1.0373(3) 0.0428(8) Uani 1 1 d . . . . .
O1 O 0.7254(2) 0.9904(2) 1.0201(2) 0.0354(5) Uani 1 1 d . . . . .
O2 O 0.5591(2) 0.6645(2) 0.68847(19) 0.0265(4) Uani 1 1 d . . . . .
O3 O 0.6541(2) 0.6029(2) 1.00243(19) 0.0255(4) Uani 1 1 d . . . . .
O4 O 0.3036(2) 0.78842(19) 0.77950(18) 0.0142(4) Uani 1 1 d D . . . .
O5 O 0.1835(2) 0.62273(19) 1.03791(16) 0.0178(4) Uani 1 1 d . . . . .
O6 O 0.3560(2) 0.73126(19) 0.99240(17) 0.0148(4) Uani 1 1 d . . . . .
O7 O 0.2830(2) -0.0096(2) 0.50842(19) 0.0298(5) Uani 1 1 d . . . . .
O8 O 0.4258(3) 0.3212(2) 0.8061(2) 0.0293(5) Uani 1 1 d . . . . .
O9 O 0.3317(2) 0.3725(2) 0.48812(18) 0.0250(4) Uani 1 1 d . . . . .
O10 O 0.7050(2) 0.21793(19) 0.73055(17) 0.0134(4) Uani 1 1 d D . . . .
O11 O 0.8023(2) 0.35753(19) 0.45309(17) 0.0183(4) Uani 1 1 d . . . . .
O12 O 0.6325(2) 0.25112(19) 0.50325(17) 0.0141(4) Uani 1 1 d . . . . .
O13 O 0.5364(2) 0.96812(17) 1.18852(16) 0.0283(4) Uani 1 1 d . . . . .
H13A H 0.479(3) 0.986(3) 1.218(3) 0.042 Uiso 1 1 d . U . . .
H13B H 0.488(4) 0.898(4) 1.131(3) 0.042 Uiso 1 1 d . U . . .
O14 O 0.61789(19) 0.96178(16) 0.69785(14) 0.0227(3) Uani 1 1 d D . . . .
H14A H 0.540(2) 0.904(3) 0.640(2) 0.034 Uiso 1 1 d D U . . .
H14B H 0.686(2) 0.941(3) 0.708(3) 0.034 Uiso 1 1 d D U . . .
O15 O 0.8668(2) 0.9298(3) 0.73322(19) 0.0493(6) Uani 1 1 d D . . . .
H15A H 0.911(4) 0.934(5) 0.692(3) 0.074 Uiso 1 1 d D U . . .
H15B H 0.937(3) 0.992(3) 0.794(2) 0.074 Uiso 1 1 d D U . . .
Re1 Re 0.45589(2) 0.71761(2) 0.87707(2) 0.01041(6) Uani 1 1 d . . . . .
Re2 Re 0.53922(2) 0.27118(2) 0.62403(2) 0.00977(6) 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
0 1 0 0.0301
0 -1 0 0.0201
5 -2 0 0.0753
-5 2 0 0.0553
2 2 -5 0.1424
2 -3 5 0.0884
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 178.1(3) . . ?
O2 C2 Re1 176.9(2) . . ?
O3 C3 Re1 175.2(2) . . ?
C5 C4 H4 119.1 . . ?
N1 C4 H4 119.1 . . ?
N1 C4 C5 121.8(2) . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 C10 116.9(2) . . ?
C6 C5 C10 122.9(3) . . ?
C5 C6 H6 121.1 . . ?
C7 C6 C5 117.7(2) . . ?
C7 C6 H6 121.1 . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 123.2(2) . . ?
N1 C8 C7 122.5(2) . . ?
N1 C8 C9 114.3(2) . . ?
O5 C9 C8 119.1(2) . . ?
O5 C9 O6 125.9(2) . . ?
O6 C9 C8 115.0(2) . . ?
N2 C10 C5 175.4(3) . . ?
O7 C11 Re2 179.8(3) . . ?
O8 C12 Re2 176.7(3) . . ?
O9 C13 Re2 175.7(2) . . ?
C15 C14 H14 119.3 . . ?
N3 C14 H14 119.3 . . ?
N3 C14 C15 121.5(2) . . ?
C14 C15 C16 120.7(2) . . ?
C14 C15 C20 117.2(2) . . ?
C16 C15 C20 122.1(2) . . ?
C15 C16 H16 121.3 . . ?
C15 C16 C17 117.4(2) . . ?
C17 C16 H16 121.3 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.2(2) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C19 122.9(2) . . ?
N3 C18 C17 122.9(2) . . ?
N3 C18 C19 114.2(2) . . ?
O11 C19 C18 118.0(2) . . ?
O11 C19 O12 126.5(2) . . ?
O12 C19 C18 115.5(2) . . ?
N4 C20 C15 176.4(4) . . ?
C4 N1 C8 118.3(2) . . ?
C4 N1 Re1 125.80(18) . . ?
C8 N1 Re1 115.77(16) . . ?
C14 N3 C18 118.3(2) . . ?
C14 N3 Re2 125.64(18) . . ?
C18 N3 Re2 116.06(17) . . ?
H4A O4 H4B 104(4) . . ?
Re1 O4 H4A 109(3) . . ?
Re1 O4 H4B 108(3) . . ?
C9 O6 Re1 119.79(16) . . ?
H10A O10 H10B 107(4) . . ?
Re2 O10 H10A 111(3) . . ?
Re2 O10 H10B 108(3) . . ?
C19 O12 Re2 119.20(16) . . ?
H13A O13 H13B 110(3) . . ?
H14A O14 H14B 112(3) . . ?
H15A O15 H15B 95(4) . . ?
C1 Re1 N1 172.57(10) . . ?
C1 Re1 O4 96.23(10) . . ?
C1 Re1 O6 98.01(10) . . ?
C2 Re1 C1 88.94(13) . . ?
C2 Re1 C3 85.93(12) . . ?
C2 Re1 N1 98.39(10) . . ?
C2 Re1 O4 95.10(10) . . ?
C2 Re1 O6 172.63(10) . . ?
C3 Re1 C1 87.32(12) . . ?
C3 Re1 N1 94.39(10) . . ?
C3 Re1 O4 176.31(9) . . ?
C3 Re1 O6 96.78(10) . . ?
N1 Re1 O4 81.96(8) . . ?
O6 Re1 N1 74.62(8) . . ?
O6 Re1 O4 81.78(8) . . ?
C11 Re2 N3 172.84(10) . . ?
C11 Re2 O10 95.80(10) . . ?
C11 Re2 O12 98.99(10) . . ?
C12 Re2 C11 85.72(12) . . ?
C12 Re2 C13 85.87(12) . . ?
C12 Re2 N3 100.46(11) . . ?
C12 Re2 O10 95.59(10) . . ?
C12 Re2 O12 175.10(9) . . ?
C13 Re2 C11 89.30(12) . . ?
C13 Re2 N3 94.72(10) . . ?
C13 Re2 O10 174.79(9) . . ?
C13 Re2 O12 95.49(10) . . ?
N3 Re2 O10 80.10(8) . . ?
O12 Re2 N3 74.76(8) . . ?
O12 Re2 O10 82.64(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 1.134(4) . ?
C1 Re1 1.937(3) . ?
C2 O2 1.156(4) . ?
C2 Re1 1.899(3) . ?
C3 O3 1.145(4) . ?
C3 Re1 1.905(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(4) . ?
C4 N1 1.340(3) . ?
C5 C6 1.395(4) . ?
C5 C10 1.460(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(4) . ?
C8 C9 1.516(3) . ?
C8 N1 1.361(3) . ?
C9 O5 1.229(3) . ?
C9 O6 1.271(3) . ?
C10 N2 1.123(4) . ?
C11 O7 1.136(4) . ?
C11 Re2 1.935(3) . ?
C12 O8 1.158(4) . ?
C12 Re2 1.899(3) . ?
C13 O9 1.142(4) . ?
C13 Re2 1.909(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(4) . ?
C14 N3 1.339(3) . ?
C15 C16 1.394(4) . ?
C15 C20 1.455(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.375(4) . ?
C18 C19 1.517(3) . ?
C18 N3 1.361(3) . ?
C19 O11 1.230(3) . ?
C19 O12 1.275(3) . ?
C20 N4 1.120(4) . ?
N1 Re1 2.171(2) . ?
N3 Re2 2.172(2) . ?
O4 H4A 0.820(10) . ?
O4 H4B 0.817(10) . ?
O4 Re1 2.1960(19) . ?
O6 Re1 2.1427(19) . ?
O10 H10A 0.822(10) . ?
O10 H10B 0.814(10) . ?
O10 Re2 2.1973(19) . ?
O12 Re2 2.155(2) . ?
O13 H13A 0.90(3) . ?
O13 H13B 0.82(4) . ?
O14 H14A 0.825(10) . ?
O14 H14B 0.827(10) . ?
O15 H15A 0.828(10) . ?
O15 H15B 0.828(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
O4 H4A O13 0.820(10) 1.793(13) 2.602(3) 169(4) 2_677 yes
O4 H4B O11 0.817(10) 1.881(13) 2.687(3) 169(4) 2_666 yes
O10 H10A O14 0.822(10) 1.840(12) 2.656(3) 172(4) 1_545 yes
O10 H10B O5 0.814(10) 1.911(14) 2.708(3) 166(4) 2_667 yes
C16 H16 O4 0.95 2.57 3.215(3) 125.6 1_655 yes
O13 H13A O14 0.90(3) 1.91(3) 2.797(2) 172(3) 2_677 yes
O13 H13B O6 0.82(4) 1.95(4) 2.766(3) 174(3) . yes
O14 H14A O12 0.825(10) 2.006(12) 2.825(3) 172(3) 2_666 yes
O14 H14B O15 0.827(10) 1.942(12) 2.757(3) 168(3) . yes
O15 H15A N2 0.828(10) 2.34(2) 3.122(4) 158(4) 2_666 yes
O15 H15B N4 0.828(10) 2.15(2) 2.883(4) 148(4) 2_777 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 0.7(4) . . . . ?
C5 C4 N1 C8 -1.7(4) . . . . ?
C5 C4 N1 Re1 174.54(19) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C6 C7 C8 C9 -179.6(2) . . . . ?
C6 C7 C8 N1 -0.6(4) . . . . ?
C7 C8 C9 O5 0.3(4) . . . . ?
C7 C8 C9 O6 -179.5(2) . . . . ?
C7 C8 N1 C4 1.7(4) . . . . ?
C7 C8 N1 Re1 -174.85(19) . . . . ?
C8 C9 O6 Re1 -6.7(3) . . . . ?
C9 C8 N1 C4 -179.2(2) . . . . ?
C9 C8 N1 Re1 4.2(3) . . . . ?
C10 C5 C6 C7 -179.7(3) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
C15 C14 N3 C18 1.1(4) . . . . ?
C15 C14 N3 Re2 -179.15(19) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C16 C17 C18 C19 -179.8(2) . . . . ?
C16 C17 C18 N3 0.4(4) . . . . ?
C17 C18 C19 O11 -2.9(3) . . . . ?
C17 C18 C19 O12 177.0(2) . . . . ?
C17 C18 N3 C14 -1.3(4) . . . . ?
C17 C18 N3 Re2 178.94(19) . . . . ?
C18 C19 O12 Re2 5.9(3) . . . . ?
C19 C18 N3 C14 178.9(2) . . . . ?
C19 C18 N3 Re2 -0.9(3) . . . . ?
C20 C15 C16 C17 178.9(3) . . . . ?
N1 C4 C5 C6 0.5(4) . . . . ?
N1 C4 C5 C10 -179.1(2) . . . . ?
N1 C8 C9 O5 -178.8(2) . . . . ?
N1 C8 C9 O6 1.4(3) . . . . ?
N3 C14 C15 C16 -0.1(4) . . . . ?
N3 C14 C15 C20 -179.9(3) . . . . ?
N3 C18 C19 O11 176.9(2) . . . . ?
N3 C18 C19 O12 -3.2(3) . . . . ?
O5 C9 O6 Re1 173.5(2) . . . . ?
O11 C19 O12 Re2 -174.2(2) . . . . ?
