# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_prdznre_lt_0m
_database_code_depnum_ccdc_archive 'CCDC 2252646'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-06-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(O2 Re0.5), C4 H5 N2'
_chemical_formula_sum            'C4 H5 N2 O4 Re'
_chemical_formula_weight         331.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.3382(3)
_cell_length_b                   12.9726(8)
_cell_length_c                   10.5955(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.710(2)
_cell_angle_gamma                90
_cell_volume                     718.47(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8825
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.061
_cell_measurement_theta_min      3.149
_shelx_estimated_absorpt_T_max   0.283
_shelx_estimated_absorpt_T_min   0.218
_exptl_absorpt_coefficient_mu    16.879
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1130 before and 0.0468 after correction.
The Ratio of minimum to maximum transmission is 0.6475.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.063
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16953
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.498
_diffrn_reflns_theta_min         4.203
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2393
_reflns_number_total             2681
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.123
_refine_diff_density_min         -1.240
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       0.00456(13)
_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   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         2681
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0154
_refine_ls_restrained_S_all      1.074
_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)+0.7967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0302
_refine_ls_wR_factor_ref         0.0311
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C4(H4), C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.33328(2) 0.250000 0.40247(2) 0.00705(4) Uani 1 2 d S T P . .
Re2 Re 0.59001(2) 0.750000 1.06962(2) 0.00761(4) Uani 1 2 d S T P . .
O2 O 0.3743(5) 0.250000 0.2445(2) 0.0148(5) Uani 1 2 d S T P . .
N2 N 0.8118(4) 0.48456(17) 0.8238(2) 0.0140(4) Uani 1 1 d . . . . .
O5 O 0.6032(5) 0.750000 1.2343(2) 0.0166(5) Uani 1 2 d S T P . .
C6 C 1.1794(5) 0.57117(19) 0.7827(2) 0.0135(5) Uani 1 1 d . . . . .
H6 H 1.301796 0.624540 0.806406 0.016 Uiso 1 1 calc R U . . .
O1 O 0.0087(5) 0.250000 0.4038(3) 0.0151(5) Uani 1 2 d S T P . .
O4 O 0.7443(4) 0.64070(14) 1.03048(18) 0.0165(4) Uani 1 1 d . . . . .
N1 N 0.9908(4) 0.55853(16) 0.8461(2) 0.0123(4) Uani 1 1 d . . . . .
H1 H 0.971(6) 0.601(2) 0.909(3) 0.015 Uiso 1 1 d . U . . .
C5 C 1.1951(5) 0.50489(19) 0.6809(2) 0.0120(4) Uani 1 1 d . . . . .
H5 H 1.325439 0.512684 0.632441 0.014 Uiso 1 1 calc R U . . .
O3 O 0.4680(4) 0.35996(15) 0.48029(19) 0.0203(4) Uani 1 1 d . . . . .
C4 C 1.0149(5) 0.42776(19) 0.6531(2) 0.0119(4) Uani 1 1 d . . . . .
H4 H 1.017158 0.380792 0.584524 0.014 Uiso 1 1 calc R U . . .
O6 O 0.2723(5) 0.750000 0.9864(3) 0.0149(5) Uani 1 2 d S T P . .
C3 C 0.8280(5) 0.42035(19) 0.7286(2) 0.0126(4) Uani 1 1 d . . . . .
H3 H 0.706185 0.366201 0.710438 0.015 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O2 1.732(3) . ?
Re1 O1 1.735(2) . ?
Re1 O3 1.7295(18) . ?
Re1 O3 1.7295(18) 4_565 ?
Re2 O5 1.732(3) . ?
Re2 O4 1.7320(17) . ?
Re2 O4 1.7320(18) 4_575 ?
Re2 O6 1.746(3) . ?
N2 N1 1.341(3) . ?
N2 C3 1.324(3) . ?
C6 H6 0.9500 . ?
C6 N1 1.329(3) . ?
C6 C5 1.395(4) . ?
N1 H1 0.89(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.378(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.404(4) . ?
C3 H3 0.9500 . ?

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
O2 Re1 O1 109.26(13) . . ?
O3 Re1 O2 109.81(8) . . ?
O3 Re1 O2 109.82(8) 4_565 . ?
O3 Re1 O1 108.39(8) . . ?
O3 Re1 O1 108.39(8) 4_565 . ?
O3 Re1 O3 111.13(15) . 4_565 ?
O5 Re2 O6 110.23(13) . . ?
O4 Re2 O5 108.49(8) . . ?
O4 Re2 O5 108.49(8) 4_575 . ?
O4 Re2 O4 109.90(13) 4_575 . ?
O4 Re2 O6 109.85(8) . . ?
O4 Re2 O6 109.85(8) 4_575 . ?
C3 N2 N1 115.5(2) . . ?
N1 C6 H6 120.5 . . ?
N1 C6 C5 119.0(2) . . ?
C5 C6 H6 120.5 . . ?
N2 N1 H1 113(2) . . ?
C6 N1 N2 125.8(2) . . ?
C6 N1 H1 121(2) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 C6 117.6(2) . . ?
C4 C5 H5 121.2 . . ?
C5 C4 H4 120.8 . . ?
C5 C4 C3 118.3(2) . . ?
C3 C4 H4 120.8 . . ?
N2 C3 C4 123.7(2) . . ?
N2 C3 H3 118.1 . . ?
C4 C3 H3 118.1 . . ?

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
C6 H6 O6 0.95 2.54 3.138(3) 121.5 1_655 yes
N1 H1 O4 0.89(3) 2.00(3) 2.780(3) 145(3) . yes
N1 H1 O6 0.89(3) 2.54(3) 3.119(3) 123(2) 1_655 yes
C5 H5 O3 0.95 2.43 3.236(3) 142.5 3_766 yes
C3 H3 O5 0.95 2.39 3.271(3) 153.3 2_647 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
C6 C5 C4 C3 -0.2(3) . . . . ?
N1 N2 C3 C4 -0.9(4) . . . . ?
N1 C6 C5 C4 -1.3(3) . . . . ?
C5 C6 N1 N2 1.9(4) . . . . ?
C5 C4 C3 N2 1.3(4) . . . . ?
C3 N2 N1 C6 -0.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mv137
_database_code_depnum_ccdc_archive 'CCDC 2384437'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-11-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'O4 Re, C5 H12 N'
_chemical_formula_sum            'C5 H12 N O4 Re'
_chemical_formula_weight         336.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.807(2)
_cell_length_b                   6.087(2)
_cell_length_c                   6.157(2)
_cell_angle_alpha                95.814(11)
_cell_angle_beta                 94.570(11)
_cell_angle_gamma                100.825(11)
_cell_volume                     211.57(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3433
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      3.343
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    14.328
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0794 before and 0.0390 after correction.
The Ratio of minimum to maximum transmission is 0.8181.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.640
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             156
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4129
_diffrn_reflns_point_group_measured_fraction_full 0.849
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         4.452
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_full    0.705
_reflns_Friedel_fraction_max     0.654
_reflns_number_gt                2042
_reflns_number_total             2042
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.175
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_extinction_coef       0.0190(19)
_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   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         2042
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0187
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0037P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0333
_refine_ls_wR_factor_ref         0.0333
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.926
 0.074
2. Uiso/Uaniso restraints and constraints
Uanis(C5) = Uanis(C3) = Uanis(C4)
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.30378(19) 0.7192(2) 0.29221(19) 0.00669(8) Uani 1 1 d . . . . .
O1 O 0.4182(9) 0.9986(8) 0.3981(8) 0.0158(10) Uani 1 1 d . . . . .
O2 O 0.3176(9) 0.6851(8) 0.0105(7) 0.0155(10) Uani 1 1 d . . . . .
O3 O 0.0110(8) 0.6502(8) 0.3450(8) 0.0146(10) Uani 1 1 d . . . . .
O4 O 0.4621(9) 0.5444(8) 0.4128(8) 0.0187(11) Uani 1 1 d . . . . .
N1 N 0.7992(18) 0.3280(19) 0.6191(15) 0.013(2) Uani 1 1 d . . . . .
H1A H 0.676(16) 0.264(15) 0.546(14) 0.016 Uiso 1 1 d . U . . .
H1B H 0.809(15) 0.428(14) 0.533(13) 0.016 Uiso 1 1 d . U . . .
C2 C 0.7306(19) 0.416(2) 0.8373(19) 0.012(2) Uani 1 1 d . . . . .
H2A H 0.596569 0.493111 0.814391 0.014 Uiso 1 1 calc R U . . .
H2B H 0.864737 0.525751 0.918839 0.014 Uiso 1 1 calc R U . . .
C3 C 0.661(2) 0.218(2) 0.968(2) 0.0119(16) Uani 1 1 d . . . . .
H3A H 0.622076 0.274942 1.114664 0.014 Uiso 1 1 calc R U . . .
H3B H 0.518833 0.115372 0.891690 0.014 Uiso 1 1 calc R U . . .
C4 C 0.858(2) 0.091(2) 0.996(2) 0.0119(16) Uani 1 1 d . . . . .
H4A H 0.805994 -0.040116 1.074838 0.014 Uiso 1 1 calc R U . . .
H4B H 0.995038 0.190087 1.084162 0.014 Uiso 1 1 calc R U . . .
C5 C 0.931(2) 0.010(2) 0.770(2) 0.0119(16) Uani 1 1 d . . . . .
H5A H 1.065369 -0.067165 0.791729 0.014 Uiso 1 1 calc R U . . .
H5B H 0.797853 -0.100119 0.686487 0.014 Uiso 1 1 calc R U . . .
C6 C 0.9995(19) 0.206(2) 0.642(2) 0.015(2) Uani 1 1 d . . . . .
H6A H 1.140935 0.309504 0.719034 0.018 Uiso 1 1 calc R U . . .
H6B H 1.038039 0.150999 0.494930 0.018 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 1.744(5) . ?
Re1 O2 1.736(4) . ?
Re1 O3 1.738(5) . ?
Re1 O4 1.716(5) . ?
N1 H1A 0.82(9) . ?
N1 H1B 0.84(8) . ?
N1 C2 1.506(14) . ?
N1 C6 1.499(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.526(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.503(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.545(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.507(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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
O2 Re1 O1 109.9(2) . . ?
O2 Re1 O3 108.9(2) . . ?
O3 Re1 O1 109.1(2) . . ?
O4 Re1 O1 109.9(2) . . ?
O4 Re1 O2 109.4(2) . . ?
O4 Re1 O3 109.6(2) . . ?
H1A N1 H1B 88(8) . . ?
C2 N1 H1A 106(6) . . ?
C2 N1 H1B 111(6) . . ?
C6 N1 H1A 119(7) . . ?
C6 N1 H1B 118(6) . . ?
C6 N1 C2 112.7(7) . . ?
N1 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
N1 C2 C3 108.8(9) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 110.9(10) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 C5 110.8(9) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.4(10) . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
N1 C6 C5 109.3(9) . . ?
N1 C6 H6A 109.8 . . ?
N1 C6 H6B 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?

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
N1 H1A O1 0.82(9) 2.06(9) 2.841(12) 157(8) 1_545 yes
N1 H1B O3 0.84(8) 2.12(8) 2.881(12) 151(8) 1_655 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
N1 C2 C3 C4 56.7(11) . . . . ?
C2 N1 C6 C5 59.3(11) . . . . ?
C2 C3 C4 C5 -56.5(13) . . . . ?
C3 C4 C5 C6 56.5(13) . . . . ?
C4 C5 C6 N1 -56.5(11) . . . . ?
C6 N1 C2 C3 -58.7(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.926
2 0.074

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mv57_lt_1_0ma
_database_code_depnum_ccdc_archive 'CCDC 2384438'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-05-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'O4 Re, C5 H10 N2'
_chemical_formula_sum            'C5 H10 N2 O4 Re'
_chemical_formula_weight         348.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   12.086(2)
_cell_length_b                   8.5629(14)
_cell_length_c                   8.3490(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     864.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2197
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.354
_cell_measurement_theta_min      3.371
_shelx_estimated_absorpt_T_max   0.604
_shelx_estimated_absorpt_T_min   0.263
_exptl_absorpt_coefficient_mu    14.042
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1308 before and 0.0716 after correction.
The Ratio of minimum to maximum transmission is 0.7073.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.678
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             644
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14162
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.993
_diffrn_reflns_theta_min         4.127
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1130
_reflns_number_total             1326
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.059
_refine_diff_density_min         -1.318
_refine_diff_density_rms         0.255
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.064
_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)+(0.0198P)²+1.4269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0531
_refine_ls_wR_factor_ref         0.0566
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
1.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.96058(2) 0.750000 1.04573(3) 0.00903(9) Uani 1 2 d S T P . .
N1 N 0.6267(4) 0.6714(4) 0.8487(5) 0.0115(8) Uani 1 1 d . . . . .
H1 H 0.623(5) 0.624(5) 0.773(6) 0.014 Uiso 1 1 d . U . . .
O3 O 0.9281(3) 0.5846(4) 1.1551(4) 0.0189(8) Uani 1 1 d . . . . .
O2 O 1.1006(5) 0.750000 0.9978(6) 0.0190(11) Uani 1 2 d S T P . .
C1 C 0.6482(4) 0.6194(6) 0.9970(6) 0.0116(9) Uani 1 1 d . . . . .
O1 O 0.8873(4) 0.750000 0.8691(6) 0.0209(11) Uani 1 2 d S T P . .
C3 C 0.6565(4) 0.4505(6) 1.0327(7) 0.0206(12) Uani 1 1 d . . . . .
H3A H 0.607443 0.392138 0.960939 0.031 Uiso 1 1 calc R U . . .
H3B H 0.634671 0.431662 1.144089 0.031 Uiso 1 1 calc R U . . .
H3C H 0.733003 0.415734 1.016766 0.031 Uiso 1 1 calc R U . . .
C2 C 0.6606(6) 0.750000 1.0945(8) 0.0131(14) Uani 1 2 d S T P . .
H2A H 0.734746 0.750001 1.145058 0.016 Uiso 1 2 calc R U P . .
H2B H 0.603952 0.749999 1.180099 0.016 Uiso 1 2 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O3 1.730(3) . ?
Re1 O3 1.730(3) 7_575 ?
Re1 O2 1.739(6) . ?
Re1 O1 1.720(5) . ?
N1 N1 1.347(7) 7_575 ?
N1 H1 0.75(5) . ?
N1 C1 1.341(6) . ?
C1 C3 1.481(6) . ?
C1 C2 1.391(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

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
O3 Re1 O3 109.9(2) . 7_575 ?
O3 Re1 O2 110.02(14) . . ?
O3 Re1 O2 110.02(14) 7_575 . ?
O1 Re1 O3 109.60(15) . . ?
O1 Re1 O3 109.60(15) . 7_575 ?
O1 Re1 O2 107.7(2) . . ?
N1 N1 H1 122(4) 7_575 . ?
C1 N1 N1 109.4(3) . 7_575 ?
C1 N1 H1 128(4) . . ?
N1 C1 C3 121.6(5) . . ?
N1 C1 C2 107.2(4) . . ?
C2 C1 C3 131.3(5) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C2 C1 106.9(6) . 7_575 ?
C1 C2 H2A 110.3 . . ?
C1 C2 H2A 110.3 7_575 . ?
C1 C2 H2B 110.3 . . ?
C1 C2 H2B 110.3 7_575 . ?
H2A C2 H2B 108.6 . . ?

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
N1 H1 O3 0.75(5) 2.13(5) 2.803(5) 149(5) 2_664 yes
N1 H1 O2 0.75(5) 2.52(5) 2.986(7) 122(4) 4_466 yes
C3 H3A O3 0.98 2.60 3.328(7) 131.5 2_664 yes
C3 H3B O1 0.98 2.45 3.334(7) 149.3 2_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
N1 N1 C1 C3 -178.3(4) 7_575 . . . ?
N1 N1 C1 C2 0.9(5) 7_575 . . . ?
N1 C1 C2 C1 -1.4(7) . . . 7_575 ?
C3 C1 C2 C1 177.7(4) . . . 7_575 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_piperazreo4_lt
_database_code_depnum_ccdc_archive 'CCDC 2384440'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-11-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(O4 Re), C4 H12 N2'
_chemical_formula_sum            'C4 H12 N2 O8 Re2'
_chemical_formula_weight         588.56
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2945(4)
_cell_length_b                   7.3292(4)
_cell_length_c                   7.3349(4)
_cell_angle_alpha                115.398(2)
_cell_angle_beta                 107.627(2)
_cell_angle_gamma                90.178(2)
_cell_volume                     287.83(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2754
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.58
_cell_measurement_theta_min      3.11
_shelx_estimated_absorpt_T_max   0.487
_shelx_estimated_absorpt_T_min   0.284
_exptl_absorpt_coefficient_mu    21.038
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5275
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         4.269
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1554
_reflns_number_total             1664
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         1.032
_refine_diff_density_min         -1.193
_refine_diff_density_rms         0.264
_refine_ls_extinction_coef       0.0045(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   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     80
_refine_ls_number_reflns         1664
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0218
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0105P)²+0.0458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0358
_refine_ls_wR_factor_ref         0.0367
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1C,H1D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.47296(3) 0.33710(2) 0.16755(2) 0.00748(6) Uani 1 1 d . . . . .
O1 O 0.3428(6) 0.5275(5) 0.3103(5) 0.0178(7) Uani 1 1 d . . . . .
O4 O 0.7633(5) 0.4043(4) 0.2750(4) 0.0125(6) Uani 1 1 d . . . . .
O2 O 0.3755(5) 0.2895(4) -0.0993(4) 0.0117(6) Uani 1 1 d . . . . .
O3 O 0.4008(5) 0.1176(5) 0.1805(5) 0.0156(7) Uani 1 1 d . . . . .
N1 N 0.0337(6) 0.7909(5) 0.4255(5) 0.0082(7) Uani 1 1 d . . . . .
H1A H -0.085(8) 0.731(7) 0.306(7) 0.010 Uiso 1 1 d . U . . .
H1B H 0.109(8) 0.695(7) 0.420(7) 0.010 Uiso 1 1 d . U . . .
C2 C -0.0407(7) 0.8915(6) 0.6156(6) 0.0109(8) Uani 1 1 d . . . . .
H2A H 0.092622 0.949530 0.748177 0.013 Uiso 1 1 calc R U . . .
H2B H -0.136839 0.789118 0.622521 0.013 Uiso 1 1 calc R U . . .
C1 C 0.1725(7) 0.9396(6) 0.4003(6) 0.0096(8) Uani 1 1 d . . . . .
H1C H 0.212907 0.867372 0.269372 0.012 Uiso 1 1 calc R U . . .
H1D H 0.313829 0.999457 0.524826 0.012 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 1.729(3) . ?
Re1 O4 1.730(3) . ?
Re1 O2 1.736(3) . ?
Re1 O3 1.719(3) . ?
N1 H1A 0.89(5) . ?
N1 H1B 0.84(5) . ?
N1 C2 1.491(5) . ?
N1 C1 1.500(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.519(6) 2_576 ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?

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 Re1 O4 110.93(14) . . ?
O1 Re1 O2 109.37(14) . . ?
O4 Re1 O2 110.92(14) . . ?
O3 Re1 O1 108.48(15) . . ?
O3 Re1 O4 108.78(15) . . ?
O3 Re1 O2 108.28(13) . . ?
H1A N1 H1B 103(4) . . ?
C2 N1 H1A 110(3) . . ?
C2 N1 H1B 117(3) . . ?
C2 N1 C1 112.4(3) . . ?
C1 N1 H1A 108(3) . . ?
C1 N1 H1B 106(3) . . ?
N1 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
N1 C2 C1 110.0(3) . 2_576 ?
H2A C2 H2B 108.2 . . ?
C1 C2 H2A 109.7 2_576 . ?
C1 C2 H2B 109.7 2_576 . ?
N1 C1 C2 110.1(3) . 2_576 ?
N1 C1 H1C 109.6 . . ?
N1 C1 H1D 109.6 . . ?
C2 C1 H1C 109.6 2_576 . ?
C2 C1 H1D 109.6 2_576 . ?
H1C C1 H1D 108.2 . . ?

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
N1 H1A O2 0.89(5) 1.95(5) 2.785(5) 157(4) 2_565 yes
N1 H1B O1 0.84(5) 2.05(5) 2.801(5) 148(4) . yes
N1 H1B O4 0.84(5) 2.55(5) 3.084(5) 123(4) 2_666 yes
C2 H2A O2 0.99 2.65 3.339(5) 127.1 1_566 yes
C2 H2B O3 0.99 2.44 3.085(5) 122.7 2_566 yes
C1 H1D O2 0.99 2.57 3.278(5) 128.7 1_566 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
C2 N1 C1 C2 -57.1(5) . . . 2_576 ?
C1 N1 C2 C1 57.0(5) . . . 2_576 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_repyrzn_lt
_database_code_depnum_ccdc_archive 'CCDC 2384444'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-11-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'O4 Re, C4 H5 N2'
_chemical_formula_sum            'C4 H5 N2 O4 Re'
_chemical_formula_weight         331.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.8384(5)
_cell_length_b                   8.7977(7)
_cell_length_c                   14.3012(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.293(2)
_cell_angle_gamma                90
_cell_volume                     724.93(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2809
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.93
_cell_measurement_theta_min      3.60
_shelx_estimated_absorpt_T_max   0.433
_shelx_estimated_absorpt_T_min   0.348
_exptl_absorpt_coefficient_mu    16.729
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.036
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7861
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         4.228
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1813
_reflns_number_total             2094
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         1.369
_refine_diff_density_min         -1.322
_refine_diff_density_rms         0.261
_refine_ls_extinction_coef       0.00205(17)
_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   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         2094
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0269
_refine_ls_restrained_S_all      1.061
_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)+(0.0192P)²+2.0641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0526
_refine_ls_wR_factor_ref         0.0549
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C1(H1), C4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.64283(3) 0.32154(2) 0.61480(2) 0.00770(7) Uani 1 1 d . . . . .
O2 O 0.5700(6) 0.1899(4) 0.5245(3) 0.0110(7) Uani 1 1 d . . . . .
N3 N 0.1386(8) 0.6959(5) 0.6196(3) 0.0093(8) Uani 1 1 d . . . . .
H3 H 0.159(10) 0.606(8) 0.617(4) 0.011 Uiso 1 1 d . U . . .
O1 O 0.9018(7) 0.4086(4) 0.6031(3) 0.0177(9) Uani 1 1 d . . . . .
N6 N 0.0709(8) 0.9989(5) 0.6407(3) 0.0153(10) Uani 1 1 d . . . . .
O4 O 0.6698(7) 0.2281(5) 0.7223(3) 0.0159(8) Uani 1 1 d . . . . .
O3 O 0.4254(7) 0.4567(5) 0.6065(3) 0.0184(9) Uani 1 1 d . . . . .
C2 C 0.3052(9) 0.7773(6) 0.6708(4) 0.0134(11) Uani 1 1 d . . . . .
H2 H 0.445806 0.731108 0.700031 0.016 Uiso 1 1 calc R U . . .
C5 C -0.0924(10) 0.9114(6) 0.5907(4) 0.0155(12) Uani 1 1 d . . . . .
H5 H -0.234630 0.956707 0.562599 0.019 Uiso 1 1 calc R U . . .
C1 C 0.2677(9) 0.9313(6) 0.6804(4) 0.0142(11) Uani 1 1 d . . . . .
H1 H 0.385809 0.991057 0.716392 0.017 Uiso 1 1 calc R U . . .
C4 C -0.0610(9) 0.7567(6) 0.5785(4) 0.0117(10) Uani 1 1 d . . . . .
H4 H -0.177829 0.696385 0.542190 0.014 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O2 1.735(3) . ?
Re1 O1 1.727(4) . ?
Re1 O4 1.728(4) . ?
Re1 O3 1.729(4) . ?
N3 H3 0.80(7) . ?
N3 C2 1.329(6) . ?
N3 C4 1.330(6) . ?
N6 C5 1.339(7) . ?
N6 C1 1.336(7) . ?
C2 H2 0.9500 . ?
C2 C1 1.383(8) . ?
C5 H5 0.9500 . ?
C5 C4 1.388(7) . ?
C1 H1 0.9500 . ?
C4 H4 0.9500 . ?

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 Re1 O2 109.69(19) . . ?
O1 Re1 O4 109.98(18) . . ?
O1 Re1 O3 109.5(2) . . ?
O4 Re1 O2 108.71(19) . . ?
O4 Re1 O3 110.4(2) . . ?
O3 Re1 O2 108.60(18) . . ?
C2 N3 H3 117(4) . . ?
C2 N3 C4 122.5(5) . . ?
C4 N3 H3 120(4) . . ?
C1 N6 C5 117.4(5) . . ?
N3 C2 H2 121.0 . . ?
N3 C2 C1 118.0(5) . . ?
C1 C2 H2 121.0 . . ?
N6 C5 H5 118.9 . . ?
N6 C5 C4 122.3(5) . . ?
C4 C5 H5 118.9 . . ?
N6 C1 C2 122.2(5) . . ?
N6 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
N3 C4 C5 117.6(5) . . ?
N3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?

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
N3 H3 O1 0.80(7) 2.28(6) 2.872(6) 131(5) 1_455 yes
N3 H3 O3 0.80(7) 2.06(6) 2.714(6) 139(6) . yes
C2 H2 O4 0.95 2.34 3.226(6) 155.3 2_656 yes
C5 H5 O2 0.95 2.37 3.191(6) 144.8 1_465 yes
C5 H5 O2 0.95 2.50 3.131(6) 123.7 3_566 yes
C4 H4 O2 0.95 2.54 3.132(6) 120.7 3_566 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
N3 C2 C1 N6 0.5(9) . . . . ?
N6 C5 C4 N3 0.8(8) . . . . ?
C2 N3 C4 C5 0.0(8) . . . . ?
C5 N6 C1 C2 0.3(9) . . . . ?
C1 N6 C5 C4 -0.9(9) . . . . ?
C4 N3 C2 C1 -0.6(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kaz105
_database_code_depnum_ccdc_archive 'CCDC 2384441'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'O4 Re, C4 H7 N2'
_chemical_formula_sum            'C4 H7 N2 O4 Re'
_chemical_formula_weight         333.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0126(9)
_cell_length_b                   8.0573(10)
_cell_length_c                   14.2499(17)
_cell_angle_alpha                99.816(5)
_cell_angle_beta                 91.370(5)
_cell_angle_gamma                93.454(5)
_cell_volume                     791.45(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1537
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.441
_cell_measurement_theta_min      2.903
_shelx_estimated_absorpt_T_max   0.460
_shelx_estimated_absorpt_T_min   0.193
_exptl_absorpt_coefficient_mu    15.324
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1115 before and 0.0619 after correction.
The Ratio of minimum to maximum transmission is 0.5447.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.797
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9853
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         4.150
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2099
_reflns_number_total             2772
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.498
_refine_diff_density_min         -1.326
_refine_diff_density_rms         0.298
_refine_ls_extinction_coef       0.0034(3)
_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   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N11(H11), N12(H12), C4(H4), C5(H5), C14(H14), C15(H15)
1.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.82140(7) 1.05772(6) 0.83231(4) 0.0189(2) Uani 1 1 d . . . . .
Re2 Re 0.18747(8) 0.47522(6) 0.30300(4) 0.0213(2) Uani 1 1 d . . . . .
O1 O 1.0361(14) 0.9723(11) 0.8153(7) 0.034(3) Uani 1 1 d . . . . .
O2 O 0.6984(14) 0.9697(11) 0.9159(7) 0.033(3) Uani 1 1 d . . . . .
O3 O 0.6895(15) 1.0210(13) 0.7262(7) 0.041(3) Uani 1 1 d . . . . .
O4 O 0.8606(13) 1.2696(11) 0.8718(7) 0.029(2) Uani 1 1 d . . . . .
O5 O -0.0223(14) 0.5692(12) 0.3126(7) 0.035(3) Uani 1 1 d . . . . .
O6 O 0.2216(14) 0.3788(12) 0.1870(7) 0.033(3) Uani 1 1 d . . . . .
O7 O 0.1832(15) 0.3258(12) 0.3750(8) 0.040(3) Uani 1 1 d . . . . .
O8 O 0.3696(13) 0.6226(13) 0.3400(7) 0.035(3) Uani 1 1 d . . . . .
N1 N 0.2467(16) 1.0633(14) 0.4696(9) 0.026(3) Uani 1 1 d . . . . .
H1 H 0.240865 1.111457 0.418722 0.031 Uiso 1 1 calc R U . . .
N2 N 0.2906(14) 0.9061(13) 0.4703(8) 0.019(3) Uani 1 1 d . . . . .
H2 H 0.320540 0.833775 0.420100 0.023 Uiso 1 1 calc R U . . .
N11 N 0.2827(16) 1.3108(14) 0.9926(9) 0.028(3) Uani 1 1 d . . . . .
H11 H 0.265995 1.258998 1.041698 0.033 Uiso 1 1 calc R U . . .
N12 N 0.2531(16) 1.4727(13) 0.9919(8) 0.021(3) Uani 1 1 d . . . . .
H12 H 0.211148 1.543756 1.039659 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2825(19) 0.8750(18) 0.5583(11) 0.027(3) Uani 1 1 d . . . . .
C4 C 0.232(2) 1.024(2) 0.6157(11) 0.035(4) Uani 1 1 d . . . . .
H4 H 0.214039 1.042653 0.682457 0.042 Uiso 1 1 calc R U . . .
C5 C 0.214(2) 1.135(2) 0.5557(13) 0.040(4) Uani 1 1 d . . . . .
H5 H 0.181638 1.249011 0.573677 0.048 Uiso 1 1 calc R U . . .
C6 C 0.319(2) 0.705(2) 0.5833(14) 0.054(5) Uani 1 1 d . . . . .
H6A H 0.368042 0.720029 0.649378 0.081 Uiso 1 1 calc R U . . .
H6B H 0.413503 0.651379 0.540643 0.081 Uiso 1 1 calc R U . . .
H6C H 0.199560 0.634083 0.576125 0.081 Uiso 1 1 calc R U . . .
C13 C 0.2984(18) 1.5101(17) 0.9048(9) 0.020(3) Uani 1 1 d . . . . .
C14 C 0.3499(18) 1.3616(18) 0.8485(12) 0.032(4) Uani 1 1 d . . . . .
H14 H 0.383536 1.346961 0.783578 0.038 Uiso 1 1 calc R U . . .
C15 C 0.3418(18) 1.2388(17) 0.9070(10) 0.023(3) Uani 1 1 d . . . . .
H15 H 0.372713 1.124703 0.889405 0.028 Uiso 1 1 calc R U . . .
C16 C 0.281(2) 1.6774(18) 0.8811(11) 0.040(4) Uani 1 1 d . . . . .
H16A H 0.404204 1.718315 0.859233 0.059 Uiso 1 1 calc R U . . .
H16B H 0.245395 1.754980 0.937595 0.059 Uiso 1 1 calc R U . . .
H16C H 0.183128 1.671626 0.830324 0.059 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 1.699(9) . ?
Re1 O2 1.712(10) . ?
Re1 O3 1.725(10) . ?
Re1 O4 1.708(9) . ?
Re2 O5 1.693(9) . ?
Re2 O6 1.730(9) . ?
Re2 O7 1.709(10) . ?
Re2 O8 1.700(10) . ?
N1 H1 0.8800 . ?
N1 N2 1.323(14) . ?
N1 C5 1.297(19) . ?
N2 H2 0.8800 . ?
N2 C3 1.322(17) . ?
N11 H11 0.8800 . ?
N11 N12 1.335(15) . ?
N11 C15 1.345(17) . ?
N12 H12 0.8800 . ?
N12 C13 1.366(16) . ?
C3 C4 1.40(2) . ?
C3 C6 1.51(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.35(2) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C13 C14 1.394(18) . ?
C13 C16 1.456(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.40(2) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 Re1 O2 110.3(5) . . ?
O1 Re1 O3 109.4(5) . . ?
O1 Re1 O4 108.6(5) . . ?
O2 Re1 O3 109.3(5) . . ?
O4 Re1 O2 109.0(4) . . ?
O4 Re1 O3 110.2(5) . . ?
O5 Re2 O6 111.5(5) . . ?
O5 Re2 O7 108.1(5) . . ?
O5 Re2 O8 109.1(5) . . ?
O7 Re2 O6 109.0(5) . . ?
O8 Re2 O6 109.7(5) . . ?
O8 Re2 O7 109.3(5) . . ?
N2 N1 H1 125.3 . . ?
C5 N1 H1 125.3 . . ?
C5 N1 N2 109.4(12) . . ?
N1 N2 H2 125.4 . . ?
C3 N2 N1 109.2(11) . . ?
C3 N2 H2 125.4 . . ?
N12 N11 H11 125.1 . . ?
N12 N11 C15 109.7(12) . . ?
C15 N11 H11 125.1 . . ?
N11 N12 H12 125.6 . . ?
N11 N12 C13 108.8(11) . . ?
C13 N12 H12 125.6 . . ?
N2 C3 C4 106.7(12) . . ?
N2 C3 C6 122.7(14) . . ?
C4 C3 C6 130.6(15) . . ?
C3 C4 H4 127.4 . . ?
C5 C4 C3 105.2(14) . . ?
C5 C4 H4 127.4 . . ?
N1 C5 C4 109.6(14) . . ?
N1 C5 H5 125.2 . . ?
C4 C5 H5 125.2 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N12 C13 C14 107.5(12) . . ?
N12 C13 C16 122.4(12) . . ?
C14 C13 C16 130.0(14) . . ?
C13 C14 H14 127.0 . . ?
C13 C14 C15 106.0(13) . . ?
C15 C14 H14 127.0 . . ?
N11 C15 C14 107.8(12) . . ?
N11 C15 H15 126.1 . . ?
C14 C15 H15 126.1 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
N1 H1 O3 0.88 2.24 2.810(16) 122.6 2_676 yes
N1 H1 O7 0.88 1.99 2.747(15) 142.9 1_565 yes
N2 H2 O8 0.88 1.94 2.780(15) 160.4 . yes
N11 H11 O2 0.88 2.06 2.803(15) 141.3 2_677 yes
N11 H11 O6 0.88 2.17 2.780(15) 126.1 1_566 yes
N12 H12 O4 0.88 1.89 2.760(14) 168.3 2_687 yes
C4 H4 O1 0.95 2.42 3.267(18) 148.3 1_455 yes
C5 H5 O5 0.95 2.34 3.158(18) 143.4 2_576 yes
C14 H14 O8 0.95 2.53 3.382(19) 149.4 2_676 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
N1 N2 C3 C4 -0.6(15) . . . . ?
N1 N2 C3 C6 178.2(12) . . . . ?
N2 N1 C5 C4 -1.2(18) . . . . ?
N2 C3 C4 C5 -0.1(16) . . . . ?
N11 N12 C13 C14 2.8(14) . . . . ?
N11 N12 C13 C16 179.9(13) . . . . ?
N12 N11 C15 C14 -0.1(15) . . . . ?
N12 C13 C14 C15 -2.8(15) . . . . ?
C3 C4 C5 N1 0.8(17) . . . . ?
C5 N1 N2 C3 1.1(16) . . . . ?
C6 C3 C4 C5 -178.8(15) . . . . ?
C13 C14 C15 N11 1.8(15) . . . . ?
C15 N11 N12 C13 -1.6(15) . . . . ?
C16 C13 C14 C15 -179.6(14) . . . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT910_kaz105              
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 14 Note
RESPONSE: Closed by beamstop.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_triazreo4_lt_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2384439'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-06-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(O2 Re0.5), C2 H4 N3'
_chemical_formula_sum            'C2 H4 N3 O4 Re'
_chemical_formula_weight         320.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.1704(2)
_cell_length_b                   12.0115(6)
_cell_length_c                   9.9500(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.5830(10)
_cell_angle_gamma                90
_cell_volume                     615.96(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7571
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.071
_cell_measurement_theta_min      3.392
_shelx_estimated_absorpt_T_max   0.184
_shelx_estimated_absorpt_T_min   0.111
_exptl_absorpt_coefficient_mu    19.686
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1334 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.5270.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10224
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.991
_diffrn_reflns_theta_min         4.109
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1776
_reflns_number_total             1867
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.866
_refine_diff_density_min         -1.507
_refine_diff_density_rms         0.241
_refine_ls_extinction_coef       0.0081(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   1.163
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         1867
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0208
_refine_ls_restrained_S_all      1.162
_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)+(0.0121P)²+2.0982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0488
_refine_ls_wR_factor_ref         0.0495
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N4-H4
 0.88 with sigma of 0.02
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Re01 Re 0.15408(4) 0.750000 0.58309(2) 0.00386(8) Uani 1 2 d S T P . .
Re02 Re 0.98237(4) 0.250000 -0.07304(2) 0.00368(7) Uani 1 2 d S T P . .
O13 O 0.1053(9) 0.750000 0.7531(4) 0.0112(8) Uani 1 2 d S T P . .
O11 O 0.0199(6) 0.6304(2) 0.5100(3) 0.0088(5) Uani 1 1 d . . . . .
O22 O 1.2937(8) 0.250000 0.0057(4) 0.0117(8) Uani 1 2 d S T P . .
O12 O 0.4818(8) 0.750000 0.5650(4) 0.0140(9) Uani 1 2 d S T P . .
O23 O 0.8206(6) 0.3683(2) -0.0254(3) 0.0084(5) Uani 1 1 d . . . . .
O21 O 0.9904(9) 0.250000 -0.2457(4) 0.0131(8) Uani 1 2 d S T P . .
N1 N 0.5092(7) 0.4426(3) 0.1666(3) 0.0072(6) Uani 1 1 d . . . . .
H1 H 0.553(11) 0.398(5) 0.106(5) 0.009 Uiso 1 1 d . U . . .
N4 N 0.2943(6) 0.5248(3) 0.3097(3) 0.0075(6) Uani 1 1 d D . . . .
H4 H 0.165(7) 0.549(4) 0.353(5) 0.009 Uiso 1 1 d D U . . .
N2 N 0.6802(7) 0.5161(3) 0.2311(4) 0.0134(7) Uani 1 1 d . . . . .
C5 C 0.2795(8) 0.4484(3) 0.2131(4) 0.0097(7) Uani 1 1 d . . . . .
H5 H 0.130768 0.405936 0.183350 0.012 Uiso 1 1 calc R U . . .
C3 C 0.5405(8) 0.5651(4) 0.3180(4) 0.0127(8) Uani 1 1 d . . . . .
H3 H 0.603263 0.621612 0.378962 0.015 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Re01 O13 1.730(4) . ?
Re01 O11 1.730(3) 4_575 ?
Re01 O11 1.730(3) . ?
Re01 O12 1.718(4) . ?
Re02 O22 1.733(4) . ?
Re02 O23 1.734(3) . ?
Re02 O23 1.734(3) 4_565 ?
Re02 O21 1.721(4) . ?
N1 H1 0.85(6) . ?
N1 N2 1.373(5) . ?
N1 C5 1.310(5) . ?
N4 H4 0.874(19) . ?
N4 C5 1.327(5) . ?
N4 C3 1.358(5) . ?
N2 C3 1.310(5) . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?

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
O11 Re01 O13 109.04(12) 4_575 . ?
O11 Re01 O13 109.04(12) . . ?
O11 Re01 O11 112.26(19) . 4_575 ?
O12 Re01 O13 108.9(2) . . ?
O12 Re01 O11 108.77(12) . 4_575 ?
O12 Re01 O11 108.77(12) . . ?
O22 Re02 O23 109.11(12) . 4_565 ?
O22 Re02 O23 109.11(12) . . ?
O23 Re02 O23 110.07(19) 4_565 . ?
O21 Re02 O22 110.8(2) . . ?
O21 Re02 O23 108.86(12) . . ?
O21 Re02 O23 108.86(12) . 4_565 ?
N2 N1 H1 122(4) . . ?
C5 N1 H1 126(4) . . ?
C5 N1 N2 111.6(3) . . ?
C5 N4 H4 126(4) . . ?
C5 N4 C3 106.8(3) . . ?
C3 N4 H4 127(4) . . ?
C3 N2 N1 103.2(3) . . ?
N1 C5 N4 106.9(4) . . ?
N1 C5 H5 126.5 . . ?
N4 C5 H5 126.5 . . ?
N4 C3 H3 124.3 . . ?
N2 C3 N4 111.3(4) . . ?
N2 C3 H3 124.3 . . ?

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
N1 H1 O22 0.85(6) 2.40(6) 2.978(4) 126(5) 1_455 yes
N1 H1 O23 0.85(6) 2.01(6) 2.744(4) 145(5) . yes
N4 H4 O11 0.874(19) 2.04(3) 2.836(4) 152(5) . yes
C5 H5 O13 0.95 2.35 3.139(5) 140.2 2_546 yes
C5 H5 O23 0.95 2.56 3.360(5) 141.9 1_455 yes
C3 H3 O11 0.95 2.43 3.107(5) 128.1 1_655 yes
C3 H3 O12 0.95 2.53 3.344(5) 144.2 . 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
N1 N2 C3 N4 0.2(5) . . . . ?
N2 N1 C5 N4 -0.6(5) . . . . ?
C5 N1 N2 C3 0.2(5) . . . . ?
C5 N4 C3 N2 -0.5(5) . . . . ?
C3 N4 C5 N1 0.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3195_lt_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2384443'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-07-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'O4 Re, C4 H7 N2'
_chemical_formula_sum            'C4 H7 N2 O4 Re'
_chemical_formula_weight         333.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.4022(3)
_cell_length_b                   14.7984(9)
_cell_length_c                   9.4457(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.184(3)
_cell_angle_gamma                90
_cell_volume                     753.11(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2958
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.662
_cell_measurement_theta_min      3.502
_shelx_estimated_absorpt_T_max   0.644
_shelx_estimated_absorpt_T_min   0.399
_exptl_absorpt_coefficient_mu    16.104
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1208 before and 0.0681 after correction.
The Ratio of minimum to maximum transmission is 0.6603.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.940
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22667
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         4.327
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1762
_reflns_number_total             2192
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.789
_refine_diff_density_min         -1.826
_refine_diff_density_rms         0.293
_refine_ls_extinction_coef       0.00112(15)
_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   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         2192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.060
_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)+(0.0176P)²+4.5245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0545
_refine_ls_wR_factor_ref         0.0597
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
1.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 1.34011(4) 0.36222(2) 0.29341(2) 0.00983(8) Uani 1 1 d . . . . .
O1 O 1.5241(9) 0.3800(3) 0.4475(5) 0.0202(10) Uani 1 1 d . . . . .
O2 O 1.0328(8) 0.3580(3) 0.3351(4) 0.0148(8) Uani 1 1 d . . . . .
O3 O 1.3776(8) 0.4502(3) 0.1792(5) 0.0174(9) Uani 1 1 d . . . . .
O4 O 1.4186(8) 0.2617(3) 0.2128(5) 0.0183(9) Uani 1 1 d . . . . .
N1 N 1.8276(10) 0.1454(3) 0.2212(5) 0.0126(10) Uani 1 1 d . . . . .
N5 N 1.9690(10) 0.1069(3) 0.1256(6) 0.0137(10) Uani 1 1 d . . . . .
H5 H 1.942(14) 0.111(5) 0.045(8) 0.016 Uiso 1 1 d . U . . .
C2 C 1.9254(11) 0.1278(4) 0.3511(6) 0.0134(11) Uani 1 1 d . . . . .
C3 C 2.1367(11) 0.0761(4) 0.3383(6) 0.0136(11) Uani 1 1 d . . . . .
H3 H 2.244294 0.052514 0.413345 0.016 Uiso 1 1 calc R U . . .
C4 C 2.1591(12) 0.0659(4) 0.1952(7) 0.0142(11) Uani 1 1 d . . . . .
H4 H 2.288899 0.034676 0.153215 0.017 Uiso 1 1 calc R U . . .
C6 C 1.8088(13) 0.1608(4) 0.4794(7) 0.0203(14) Uani 1 1 d . . . . .
H6A H 1.929492 0.196730 0.537885 0.030 Uiso 1 1 calc R U . . .
H6B H 1.755522 0.109111 0.534423 0.030 Uiso 1 1 calc R U . . .
H6C H 1.664526 0.198379 0.450305 0.030 Uiso 1 1 calc R U . . .
H1 H 1.693(15) 0.174(5) 0.192(8) 0.024 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 1.722(5) . ?
Re1 O2 1.735(4) . ?
Re1 O3 1.712(4) . ?
Re1 O4 1.737(4) . ?
N1 N5 1.350(7) . ?
N1 C2 1.326(8) . ?
N1 H1 0.87(8) . ?
N5 H5 0.77(7) . ?
N5 C4 1.325(8) . ?
C2 C3 1.386(8) . ?
C2 C6 1.489(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(8) . ?
C4 H4 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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 Re1 O2 108.5(2) . . ?
O1 Re1 O4 110.9(2) . . ?
O2 Re1 O4 109.7(2) . . ?
O3 Re1 O1 109.2(2) . . ?
O3 Re1 O2 109.2(2) . . ?
O3 Re1 O4 109.3(2) . . ?
N5 N1 H1 120(5) . . ?
C2 N1 N5 109.2(5) . . ?
C2 N1 H1 131(5) . . ?
N1 N5 H5 123(6) . . ?
C4 N5 N1 108.5(5) . . ?
C4 N5 H5 128(6) . . ?
N1 C2 C3 107.6(5) . . ?
N1 C2 C6 121.7(6) . . ?
C3 C2 C6 130.7(6) . . ?
C2 C3 H3 126.9 . . ?
C4 C3 C2 106.2(5) . . ?
C4 C3 H3 126.9 . . ?
N5 C4 C3 108.5(6) . . ?
N5 C4 H4 125.8 . . ?
C3 C4 H4 125.8 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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
N5 H5 O2 0.77(7) 2.12(7) 2.839(7) 154(7) 4_665 yes
N1 H1 O4 0.87(8) 2.00(8) 2.798(7) 154(7) . 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
N1 N5 C4 C3 1.5(7) . . . . ?
N1 C2 C3 C4 1.0(7) . . . . ?
N5 N1 C2 C3 -0.1(7) . . . . ?
N5 N1 C2 C6 -179.4(5) . . . . ?
C2 N1 N5 C4 -0.9(7) . . . . ?
C2 C3 C4 N5 -1.6(7) . . . . ?
C6 C2 C3 C4 -179.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_picolre_lt_0m
_database_code_depnum_ccdc_archive 'CCDC 2384445'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'O4 Re, C6 H5 N O2, C6 H6 N O2'
_chemical_formula_sum            'C12 H11 N2 O8 Re'
_chemical_formula_weight         497.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7017(9)
_cell_length_b                   11.3642(9)
_cell_length_c                   12.4987(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.006(3)
_cell_angle_gamma                90
_cell_volume                     1461.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1809
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.814
_cell_measurement_theta_min      3.392
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.362
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1167 before and 0.0770 after correction.
The Ratio of minimum to maximum transmission is 0.7533.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1143
_diffrn_reflns_av_unetI/netI     0.0899
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25068
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         4.097
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3034
_reflns_number_total             4241
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.033
_refine_diff_density_min         -1.354
_refine_diff_density_rms         0.262
_refine_ls_extinction_coef       0.00133(14)
_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   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0139P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0871
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N13-H13 = N3-H3
 0.86 with sigma of 0.02
 O2-H2
 0.8 with sigma of 0.1
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C15(H15), C5(H5), C17(H17), C14(H14), C6(H6), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 1.01077(2) 0.31351(2) 0.22928(2) 0.01770(9) Uani 1 1 d . . . . .
O12 O 0.4952(4) 0.3128(4) 0.1242(4) 0.0276(11) Uani 1 1 d . . . . .
O2 O 0.3899(5) 0.4974(4) 0.3046(4) 0.0268(11) Uani 1 1 d D . . . .
H2 H 0.446(6) 0.489(6) 0.256(5) 0.040 Uiso 1 1 d D U . . .
O11 O 0.5449(4) 0.4951(4) 0.1930(4) 0.0210(10) Uani 1 1 d . . . . .
O1 O 0.4876(5) 0.3444(4) 0.4063(4) 0.0309(12) Uani 1 1 d . . . . .
O6 O 1.0157(4) 0.4658(4) 0.2388(3) 0.0212(10) Uani 1 1 d . . . . .
N3 N 0.3345(5) 0.3691(4) 0.5439(4) 0.0180(11) Uani 1 1 d D . . . .
H3 H 0.390(5) 0.314(4) 0.549(5) 0.022 Uiso 1 1 d D U . . .
N13 N 0.6487(5) 0.3411(4) -0.0140(5) 0.0193(12) Uani 1 1 d D . . . .
H13 H 0.599(5) 0.283(4) -0.012(5) 0.023 Uiso 1 1 d D U . . .
O5 O 0.8736(5) 0.2636(4) 0.2606(4) 0.0362(13) Uani 1 1 d . . . . .
O4 O 1.0075(5) 0.2728(4) 0.0958(4) 0.0316(12) Uani 1 1 d . . . . .
C1 C 0.4074(6) 0.4234(5) 0.3843(5) 0.0181(13) Uani 1 1 d . . . . .
C11 C 0.5546(6) 0.4065(5) 0.1321(5) 0.0178(13) Uani 1 1 d . . . . .
O3 O 1.1490(5) 0.2563(4) 0.3195(4) 0.0375(13) Uani 1 1 d . . . . .
C12 C 0.6476(6) 0.4248(5) 0.0626(5) 0.0169(13) Uani 1 1 d . . . . .
C4 C 0.2676(6) 0.3760(5) 0.6186(5) 0.0202(14) Uani 1 1 d . . . . .
H4 H 0.281035 0.319974 0.677088 0.024 Uiso 1 1 calc R U . . .
C2 C 0.3196(6) 0.4445(5) 0.4584(5) 0.0172(13) Uani 1 1 d . . . . .
C7 C 0.2312(6) 0.5341(5) 0.4467(6) 0.0226(15) Uani 1 1 d . . . . .
H7 H 0.218352 0.587551 0.386223 0.027 Uiso 1 1 calc R U . . .
C15 C 0.8058(6) 0.4387(6) -0.0777(5) 0.0247(15) Uani 1 1 d . . . . .
H15 H 0.861042 0.441791 -0.125511 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1779(6) 0.4658(5) 0.6102(5) 0.0214(14) Uani 1 1 d . . . . .
H5 H 0.129207 0.471923 0.663073 0.026 Uiso 1 1 calc R U . . .
C17 C 0.7278(6) 0.5201(6) 0.0680(5) 0.0219(14) Uani 1 1 d . . . . .
H17 H 0.728215 0.581177 0.120055 0.026 Uiso 1 1 calc R U . . .
C14 C 0.7231(6) 0.3460(6) -0.0828(6) 0.0248(15) Uani 1 1 d . . . . .
H14 H 0.718965 0.285013 -0.135705 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1599(6) 0.5460(6) 0.5248(5) 0.0216(14) Uani 1 1 d . . . . .
H6 H 0.099810 0.608847 0.518866 0.026 Uiso 1 1 calc R U . . .
C16 C 0.8082(6) 0.5282(6) -0.0016(6) 0.0254(15) Uani 1 1 d . . . . .
H16 H 0.864063 0.594063 0.002615 0.030 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O6 1.735(4) . ?
Re1 O5 1.717(5) . ?
Re1 O4 1.722(5) . ?
Re1 O3 1.721(4) . ?
O12 C11 1.229(7) . ?
O2 H2 0.97(6) . ?
O2 C1 1.278(7) . ?
O11 C11 1.283(7) . ?
O1 C1 1.221(7) . ?
N3 H3 0.855(19) . ?
N3 C4 1.325(8) . ?
N3 C2 1.344(8) . ?
N13 H13 0.853(19) . ?
N13 C12 1.351(8) . ?
N13 C14 1.325(8) . ?
C1 C2 1.509(8) . ?
C11 C12 1.505(8) . ?
C12 C17 1.373(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(8) . ?
C2 C7 1.369(8) . ?
C7 H7 0.9500 . ?
C7 C6 1.401(9) . ?
C15 H15 0.9500 . ?
C15 C14 1.366(8) . ?
C15 C16 1.388(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(9) . ?
C17 H17 0.9500 . ?
C17 C16 1.385(9) . ?
C14 H14 0.9500 . ?
C6 H6 0.9500 . ?
C16 H16 0.9500 . ?

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
O5 Re1 O6 109.0(2) . . ?
O5 Re1 O4 110.0(2) . . ?
O5 Re1 O3 111.1(3) . . ?
O4 Re1 O6 109.1(2) . . ?
O3 Re1 O6 109.1(2) . . ?
O3 Re1 O4 108.5(2) . . ?
C1 O2 H2 116(4) . . ?
C4 N3 H3 120(5) . . ?
C4 N3 C2 123.6(5) . . ?
C2 N3 H3 117(5) . . ?
C12 N13 H13 114(5) . . ?
C14 N13 H13 123(5) . . ?
C14 N13 C12 123.7(6) . . ?
O2 C1 C2 113.1(5) . . ?
O1 C1 O2 127.0(6) . . ?
O1 C1 C2 119.8(6) . . ?
O12 C11 O11 127.0(6) . . ?
O12 C11 C12 118.8(5) . . ?
O11 C11 C12 114.1(5) . . ?
N13 C12 C11 116.6(5) . . ?
N13 C12 C17 117.6(6) . . ?
C17 C12 C11 125.8(6) . . ?
N3 C4 H4 120.4 . . ?
N3 C4 C5 119.2(6) . . ?
C5 C4 H4 120.4 . . ?
N3 C2 C1 115.4(5) . . ?
N3 C2 C7 119.1(6) . . ?
C7 C2 C1 125.5(6) . . ?
C2 C7 H7 120.3 . . ?
C2 C7 C6 119.3(6) . . ?
C6 C7 H7 120.3 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.1(6) . . ?
C16 C15 H15 120.4 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.5(6) . . ?
C6 C5 H5 120.3 . . ?
C12 C17 H17 119.7 . . ?
C12 C17 C16 120.6(6) . . ?
C16 C17 H17 119.7 . . ?
N13 C14 C15 120.0(6) . . ?
N13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C7 C6 H6 120.4 . . ?
C5 C6 C7 119.3(6) . . ?
C5 C6 H6 120.4 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(6) . . ?
C17 C16 H16 120.5 . . ?

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
O2 H2 O11 0.97(6) 1.49(6) 2.444(6) 169(7) . yes
N3 H3 O12 0.855(19) 1.91(4) 2.700(6) 153(6) 4_566 yes
N13 H13 O1 0.853(19) 1.97(4) 2.731(7) 148(6) 4_565 yes
C15 H15 O6 0.95 2.42 3.317(8) 156.5 3_765 yes
C5 H5 O6 0.95 2.34 3.258(7) 163.4 3_666 yes
C17 H17 O3 0.95 2.39 3.146(8) 136.3 2_755 yes
C14 H14 O5 0.95 2.43 3.116(9) 129.0 4_565 yes
C6 H6 O4 0.95 2.44 3.261(8) 145.0 2_655 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
O12 C11 C12 N13 7.3(9) . . . . ?
O12 C11 C12 C17 -174.8(6) . . . . ?
O2 C1 C2 N3 -179.8(5) . . . . ?
O2 C1 C2 C7 -1.6(9) . . . . ?
O11 C11 C12 N13 -171.4(5) . . . . ?
O11 C11 C12 C17 6.5(9) . . . . ?
O1 C1 C2 N3 -2.2(8) . . . . ?
O1 C1 C2 C7 176.0(6) . . . . ?
N3 C4 C5 C6 0.0(9) . . . . ?
N3 C2 C7 C6 0.9(9) . . . . ?
N13 C12 C17 C16 -1.1(9) . . . . ?
C1 C2 C7 C6 -177.2(5) . . . . ?
C11 C12 C17 C16 -179.0(6) . . . . ?
C12 N13 C14 C15 0.8(10) . . . . ?
C12 C17 C16 C15 0.4(9) . . . . ?
C4 N3 C2 C1 178.5(5) . . . . ?
C4 N3 C2 C7 0.2(9) . . . . ?
C4 C5 C6 C7 1.1(9) . . . . ?
C2 N3 C4 C5 -0.7(9) . . . . ?
C2 C7 C6 C5 -1.6(9) . . . . ?
C14 N13 C12 C11 178.6(6) . . . . ?
C14 N13 C12 C17 0.5(9) . . . . ?
C14 C15 C16 C17 0.9(9) . . . . ?
C16 C15 C14 N13 -1.5(9) . . . . ?

# end Validation Reply Form
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT910_picolre_lt_0m       
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 12 Note
RESPONSE: Closed by beamstop.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_reprmdn
_database_code_depnum_ccdc_archive 'CCDC 2384442'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'O4 Re, C4 H5 N2'
_chemical_formula_sum            'C4 H5 N2 O4 Re'
_chemical_formula_weight         331.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8128(3)
_cell_length_b                   9.7587(3)
_cell_length_c                   7.4027(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.9760(10)
_cell_angle_gamma                90
_cell_volume                     693.45(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9297
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      35.160
_cell_measurement_theta_min      2.977
_shelx_estimated_absorpt_T_max   0.274
_shelx_estimated_absorpt_T_min   0.179
_exptl_absorpt_coefficient_mu    17.488
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0990 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.6587.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.173
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            37290
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.986
_diffrn_reflns_theta_min         4.177
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2834
_reflns_number_total             3041
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         1.190
_refine_diff_density_min         -1.007
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       0.00303(13)
_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   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     104
_refine_ls_number_reflns         3041
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0171
_refine_ls_R_factor_gt           0.0143
_refine_ls_restrained_S_all      1.094
_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)+(0.0113P)²+0.7995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0299
_refine_ls_wR_factor_ref         0.0305
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N2-H2
 0.88 with sigma of 0.02
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.34595(2) 0.38267(2) 0.31771(2) 0.00614(3) Uani 1 1 d . . . . .
O1 O 0.46393(16) 0.27379(16) 0.4522(2) 0.0147(3) Uani 1 1 d . . . . .
O2 O 0.42909(15) 0.48127(15) 0.1775(2) 0.0103(2) Uani 1 1 d . . . . .
O3 O 0.21359(15) 0.28922(16) 0.1808(2) 0.0133(3) Uani 1 1 d . . . . .
O4 O 0.27320(16) 0.49173(16) 0.4544(2) 0.0134(3) Uani 1 1 d . . . . .
N1 N 0.85152(18) 0.23699(18) 0.3515(2) 0.0119(3) Uani 1 1 d . . . . .
N2 N 0.70123(17) 0.39101(17) 0.1669(2) 0.0090(3) Uani 1 1 d D . . . .
H2 H 0.621(2) 0.411(3) 0.111(4) 0.011 Uiso 1 1 d D U . . .
C2 C 0.7270(2) 0.2711(2) 0.2547(3) 0.0098(3) Uani 1 1 d . . . . .
H2A H 0.652671 0.207542 0.247308 0.012 Uiso 1 1 calc R U . . .
C4 C 0.8022(2) 0.4847(2) 0.1702(3) 0.0106(3) Uani 1 1 d . . . . .
H4 H 0.782701 0.569740 0.107859 0.013 Uiso 1 1 calc R U . . .
C5 C 0.9342(2) 0.4545(2) 0.2659(3) 0.0116(3) Uani 1 1 d . . . . .
H5 H 1.009152 0.516783 0.269748 0.014 Uiso 1 1 calc R U . . .
C6 C 0.9540(2) 0.3292(2) 0.3568(3) 0.0123(3) Uani 1 1 d . . . . .
H6 H 1.044222 0.307761 0.425958 0.015 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 1.7269(14) . ?
Re1 O2 1.7379(14) . ?
Re1 O3 1.7318(14) . ?
Re1 O4 1.7220(14) . ?
N1 C2 1.325(2) . ?
N1 C6 1.344(3) . ?
N2 H2 0.830(17) . ?
N2 C2 1.337(2) . ?
N2 C4 1.344(3) . ?
C2 H2A 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.373(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9500 . ?

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 Re1 O2 110.09(7) . . ?
O1 Re1 O3 110.18(8) . . ?
O3 Re1 O2 109.27(7) . . ?
O4 Re1 O1 110.58(8) . . ?
O4 Re1 O2 108.18(7) . . ?
O4 Re1 O3 108.49(7) . . ?
C2 N1 C6 116.61(17) . . ?
C2 N2 H2 120.5(19) . . ?
C2 N2 C4 121.45(17) . . ?
C4 N2 H2 118.0(19) . . ?
N1 C2 N2 122.89(18) . . ?
N1 C2 H2A 118.6 . . ?
N2 C2 H2A 118.6 . . ?
N2 C4 H4 120.8 . . ?
N2 C4 C5 118.46(18) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 121.3 . . ?
C4 C5 C6 117.41(18) . . ?
C6 C5 H5 121.3 . . ?
N1 C6 C5 123.17(18) . . ?
N1 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?

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
N2 H2 O1 0.830(17) 2.50(3) 3.000(2) 120(2) 4_565 yes
N2 H2 O2 0.830(17) 2.16(2) 2.828(2) 138(3) . yes
N2 H2 O2 0.830(17) 2.34(3) 2.887(2) 124(2) 3_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
N2 C4 C5 C6 -1.3(3) . . . . ?
C2 N1 C6 C5 -0.4(3) . . . . ?
C2 N2 C4 C5 0.3(3) . . . . ?
C4 N2 C2 N1 0.8(3) . . . . ?
C4 C5 C6 N1 1.5(3) . . . . ?
C6 N1 C2 N2 -0.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pirrolidreo4
_database_code_depnum_ccdc_archive 'CCDC 2384446'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2024-11-07 downloaded from the CCDC.
;
_audit_creation_date             2024-10-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'O4 Re, C4 H10 N'
_chemical_formula_sum            'C4 H10 N O4 Re'
_chemical_formula_weight         322.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.4974(3)
_cell_length_b                   8.7838(6)
_cell_length_c                   15.4679(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.576(3)
_cell_angle_gamma                90
_cell_volume                     742.00(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.108
_cell_measurement_theta_min      3.523
_shelx_estimated_absorpt_T_max   0.292
_shelx_estimated_absorpt_T_min   0.180
_exptl_absorpt_coefficient_mu    16.335
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1430 before and 0.0532 after correction.
The Ratio of minimum to maximum transmission is 0.4952.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.885
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            39441
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.498
_diffrn_reflns_theta_min         4.324
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2551
_reflns_number_total             2684
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_collection       'APEX3 v2019.11-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.739
_refine_diff_density_min         -2.360
_refine_diff_density_rms         0.180
_refine_ls_extinction_coef       0.00132(13)
_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   1.293
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0197
_refine_ls_restrained_S_all      1.293
_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)+3.1184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0388
_refine_ls_wR_factor_ref         0.0392
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B), C1(H1C,H1D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.04617(2) 0.83835(2) 0.10753(2) 0.00716(4) Uani 1 1 d . . . . .
O1 O 0.3467(4) 0.8603(3) 0.08684(17) 0.0163(5) Uani 1 1 d . . . . .
O4 O 0.0433(5) 0.7539(3) 0.20765(16) 0.0162(5) Uani 1 1 d . . . . .
O5 O -0.1107(4) 0.7232(3) 0.02879(15) 0.0130(4) Uani 1 1 d . . . . .
O8 O -0.0931(5) 1.0152(3) 0.10824(18) 0.0186(5) Uani 1 1 d . . . . .
C2 C 0.5999(6) 0.4818(3) 0.1513(2) 0.0109(5) Uani 1 1 d . . . . .
H2A H 0.576395 0.583968 0.124587 0.013 Uiso 1 1 calc R U . . .
H2B H 0.724299 0.488878 0.202720 0.013 Uiso 1 1 calc R U . . .
N1 N 0.5213(5) 0.2277(3) 0.09407(18) 0.0111(5) Uani 1 1 d . . . . .
H1A H 0.418(8) 0.227(5) 0.051(3) 0.013 Uiso 1 1 d . U . . .
H1B H 0.612(8) 0.151(5) 0.098(3) 0.013 Uiso 1 1 d . U . . .
C4 C 0.3945(6) 0.2483(4) 0.1738(2) 0.0129(6) Uani 1 1 d . . . . .
H4A H 0.497391 0.211633 0.226360 0.015 Uiso 1 1 calc R U . . .
H4B H 0.235696 0.194029 0.168366 0.015 Uiso 1 1 calc R U . . .
C3 C 0.3581(6) 0.4197(4) 0.1768(2) 0.0155(6) Uani 1 1 d . . . . .
H3A H 0.330447 0.453553 0.235944 0.019 Uiso 1 1 calc R U . . .
H3B H 0.218095 0.452235 0.134930 0.019 Uiso 1 1 calc R U . . .
C1 C 0.6778(6) 0.3668(4) 0.0856(2) 0.0162(6) Uani 1 1 d . . . . .
H1C H 0.650028 0.408382 0.025804 0.019 Uiso 1 1 calc R U . . .
H1D H 0.853530 0.341274 0.098964 0.019 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 1.729(2) . ?
Re1 O4 1.719(2) . ?
Re1 O5 1.735(2) . ?
Re1 O8 1.732(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.530(4) . ?
C2 C1 1.529(4) . ?
N1 H1A 0.83(5) . ?
N1 H1B 0.83(5) . ?
N1 C4 1.495(4) . ?
N1 C1 1.508(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.520(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?

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 Re1 O5 110.10(11) . . ?
O1 Re1 O8 109.49(12) . . ?
O4 Re1 O1 108.80(12) . . ?
O4 Re1 O5 109.03(12) . . ?
O4 Re1 O8 109.36(13) . . ?
O8 Re1 O5 110.03(12) . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.7(2) . . ?
H1A N1 H1B 114(4) . . ?
C4 N1 H1A 109(3) . . ?
C4 N1 H1B 111(3) . . ?
C4 N1 C1 107.3(2) . . ?
C1 N1 H1A 107(3) . . ?
C1 N1 H1B 109(3) . . ?
N1 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
N1 C4 C3 102.8(3) . . ?
H4A C4 H4B 109.1 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 C2 102.9(3) . . ?
C4 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C2 C1 H1C 110.6 . . ?
C2 C1 H1D 110.6 . . ?
N1 C1 C2 105.7(2) . . ?
N1 C1 H1C 110.6 . . ?
N1 C1 H1D 110.6 . . ?
H1C C1 H1D 108.7 . . ?

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
N1 H1A O5 0.83(5) 2.02(5) 2.812(4) 160(4) 3_565 yes
N1 H1B O8 0.83(5) 2.01(5) 2.815(4) 163(4) 1_645 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
N1 C4 C3 C2 -40.8(3) . . . . ?
C4 N1 C1 C2 -11.1(3) . . . . ?
C3 C2 C1 N1 -14.5(3) . . . . ?
C1 C2 C3 C4 34.2(3) . . . . ?
C1 N1 C4 C3 32.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
