# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_2102c
_database_code_depnum_ccdc_archive 'CCDC 2064834'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2021-02-24 deposited with the CCDC.	2021-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H19 N2 O5 Re'
_chemical_formula_weight         493.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   10.3946(4)
_cell_length_b                   7.1672(3)
_cell_length_c                   22.2958(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.2819(11)
_cell_angle_gamma                90
_cell_volume                     1656.40(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    9925
_cell_measurement_theta_min      3.98
_cell_measurement_theta_max      67.56

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.979
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    14.592
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4344
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12840
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.976
_diffrn_reflns_theta_max         67.560
_diffrn_reflns_theta_full        67.560
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2966
_reflns_number_gt                2918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0254P)²+3.3335P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00081(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2966
_refine_ls_number_parameters     219
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0675
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   1.249
_refine_ls_restrained_S_all      1.248
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
RE Re 0.53659(2) 0.68787(3) 0.28011(2) 0.02177(11) Uani 1 1 d . . . . .
O1 O 0.2924(4) 0.4741(5) 0.37509(16) 0.0486(10) Uani 1 1 d D . . . .
H1 H 0.289(7) 0.465(2) 0.3378(5) 0.073 Uiso 1 1 d D U . . .
N2 N 0.2964(4) 0.6683(5) 0.39149(16) 0.0282(8) Uani 1 1 d D . . . .
C3 C 0.2005(4) 0.7041(6) 0.4364(2) 0.0286(9) Uani 1 1 d . . . . .
C4 C 0.1996(5) 0.5539(8) 0.4854(2) 0.0417(11) Uani 1 1 d . . . . .
H4A H 0.172059 0.435954 0.467424 0.063 Uiso 1 1 calc R U . . .
H4AB H 0.140506 0.590355 0.514995 0.063 Uiso 1 1 calc R U . . .
H4AC H 0.285769 0.540576 0.504872 0.063 Uiso 1 1 calc R U . . .
C5 C 0.0664(5) 0.7178(9) 0.4037(3) 0.0492(14) Uani 1 1 d . . . . .
H5A H 0.068292 0.806128 0.370838 0.074 Uiso 1 1 calc R U . . .
H5AB H 0.005217 0.759654 0.431605 0.074 Uiso 1 1 calc R U . . .
H5AC H 0.040585 0.596178 0.387943 0.074 Uiso 1 1 calc R U . . .
C6 C 0.2564(4) 0.8912(6) 0.4605(2) 0.0301(9) Uani 1 1 d . . . . .
C7 C 0.2319(6) 1.0478(7) 0.4144(3) 0.0499(13) Uani 1 1 d . . . . .
H7A H 0.255288 1.005576 0.375345 0.075 Uiso 1 1 calc R U . . .
H7AB H 0.283667 1.155720 0.426769 0.075 Uiso 1 1 calc R U . . .
H7AC H 0.141311 1.081491 0.411924 0.075 Uiso 1 1 calc R U . . .
C8 C 0.2107(5) 0.9529(9) 0.5205(3) 0.0520(15) Uani 1 1 d . . . . .
H8A H 0.253134 1.068653 0.532834 0.078 Uiso 1 1 calc R U . . .
H8AB H 0.231592 0.857463 0.550472 0.078 Uiso 1 1 calc R U . . .
H8AC H 0.118039 0.971980 0.516433 0.078 Uiso 1 1 calc R U . . .
N9 N 0.4008(3) 0.8610(5) 0.46376(14) 0.0236(7) Uani 1 1 d D . . . .
O10 O 0.4501(3) 0.7991(5) 0.52303(14) 0.0353(8) Uani 1 1 d D . . . .
H10 H 0.501(5) 0.880(5) 0.5375(13) 0.053 Uiso 1 1 d D U . . .
C11 C 0.4224(4) 0.7028(5) 0.42287(19) 0.0244(9) Uani 1 1 d . . . . .
H11 H 0.448449 0.591671 0.447231 0.029 Uiso 1 1 calc R U . . .
C12 C 0.5277(4) 0.7484(6) 0.38173(16) 0.0246(8) Uani 1 1 d . . . . .
C13 C 0.5457(5) 0.9182(7) 0.3510(2) 0.0361(10) Uani 1 1 d . . . . .
H13 H 0.488531 1.028612 0.351103 0.043 Uiso 1 1 calc R U . . .
C14 C 0.6656(5) 0.9096(9) 0.3256(2) 0.0459(13) Uani 1 1 d . . . . .
H14 H 0.707144 1.013497 0.305062 0.055 Uiso 1 1 calc R U . . .
C15 C 0.7219(4) 0.7345(10) 0.3396(2) 0.0465(14) Uani 1 1 d . . . . .
H15 H 0.809512 0.693938 0.330660 0.056 Uiso 1 1 calc R U . . .
C16 C 0.6360(4) 0.6349(8) 0.37402(18) 0.0346(10) Uani 1 1 d . . . . .
H16 H 0.652655 0.510991 0.392614 0.041 Uiso 1 1 calc R U . . .
O1C O 0.2527(4) 0.7382(8) 0.23737(19) 0.0591(11) Uani 1 1 d . . . . .
C1C C 0.3590(5) 0.7167(8) 0.2527(2) 0.0356(11) Uani 1 1 d . . . . .
O2C O 0.6129(5) 0.7913(7) 0.15454(18) 0.0610(13) Uani 1 1 d . . . . .
C2C C 0.5825(5) 0.7517(8) 0.2007(2) 0.0375(11) Uani 1 1 d . . . . .
O3C O 0.5362(4) 0.2711(6) 0.2515(2) 0.0499(9) Uani 1 1 d . . . . .
C3C C 0.5323(4) 0.4284(7) 0.26103(19) 0.0298(9) Uani 1 1 d . . . . .


_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
RE C3C 1.907(5) . ?
RE C1C 1.911(5) . ?
RE C2C 1.923(5) . ?
RE C14 2.269(5) . ?
RE C15 2.281(4) . ?
RE C13 2.283(5) . ?
RE C16 2.296(4) . ?
RE C12 2.316(4) . ?
O1 N2 1.439(5) . ?
N2 C11 1.459(6) . ?
N2 C3 1.487(6) . ?
C3 C5 1.526(7) . ?
C3 C4 1.535(6) . ?
C3 C6 1.543(6) . ?
C6 N9 1.512(5) . ?
C6 C8 1.519(7) . ?
C6 C7 1.530(7) . ?
N9 O10 1.451(4) . ?
N9 C11 1.483(5) . ?
C11 C12 1.515(6) . ?
C12 C16 1.410(7) . ?
C12 C13 1.415(7) . ?
C13 C14 1.408(7) . ?
C14 C15 1.411(9) . ?
C15 C16 1.413(8) . ?
O1C C1C 1.143(7) . ?
O2C C2C 1.134(7) . ?
O3C C3C 1.149(6) . ?

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
C3C RE C1C 91.6(2) . . ?
C3C RE C2C 91.7(2) . . ?
C1C RE C2C 88.9(2) . . ?
C3C RE C14 141.8(2) . . ?
C1C RE C14 126.2(2) . . ?
C2C RE C14 93.8(2) . . ?
C3C RE C15 106.1(2) . . ?
C1C RE C15 157.5(2) . . ?
C2C RE C15 104.1(2) . . ?
C14 RE C15 36.1(2) . . ?
C3C RE C13 149.15(18) . . ?
C1C RE C13 97.6(2) . . ?
C2C RE C13 117.7(2) . . ?
C14 RE C13 36.03(19) . . ?
C15 RE C13 60.1(2) . . ?
C3C RE C16 92.51(19) . . ?
C1C RE C16 131.86(19) . . ?
C2C RE C16 138.9(2) . . ?
C14 RE C16 59.8(2) . . ?
C15 RE C16 36.0(2) . . ?
C13 RE C16 59.69(19) . . ?
C3C RE C12 113.52(17) . . ?
C1C RE C12 100.61(18) . . ?
C2C RE C12 152.5(2) . . ?
C14 RE C12 59.79(17) . . ?
C15 RE C12 59.81(17) . . ?
C13 RE C12 35.84(17) . . ?
C16 RE C12 35.61(17) . . ?
O1 N2 C11 107.1(4) . . ?
O1 N2 C3 109.2(3) . . ?
C11 N2 C3 105.7(3) . . ?
N2 C3 C5 108.9(4) . . ?
N2 C3 C4 113.5(4) . . ?
C5 C3 C4 109.3(4) . . ?
N2 C3 C6 97.5(3) . . ?
C5 C3 C6 114.7(4) . . ?
C4 C3 C6 112.5(4) . . ?
N9 C6 C8 111.9(4) . . ?
N9 C6 C7 104.6(4) . . ?
C8 C6 C7 109.3(5) . . ?
N9 C6 C3 103.8(3) . . ?
C8 C6 C3 115.2(4) . . ?
C7 C6 C3 111.4(4) . . ?
O10 N9 C11 105.5(3) . . ?
O10 N9 C6 111.7(3) . . ?
C11 N9 C6 106.0(3) . . ?
N2 C11 N9 104.6(3) . . ?
N2 C11 C12 114.2(3) . . ?
N9 C11 C12 110.9(3) . . ?
C16 C12 C13 107.5(4) . . ?
C16 C12 C11 124.6(4) . . ?
C13 C12 C11 127.3(4) . . ?
C16 C12 RE 71.5(2) . . ?
C13 C12 RE 70.8(2) . . ?
C11 C12 RE 129.4(3) . . ?
C14 C13 C12 108.1(5) . . ?
C14 C13 RE 71.5(3) . . ?
C12 C13 RE 73.3(2) . . ?
C13 C14 C15 108.4(5) . . ?
C13 C14 RE 72.5(3) . . ?
C15 C14 RE 72.4(3) . . ?
C14 C15 C16 107.5(5) . . ?
C14 C15 RE 71.5(3) . . ?
C16 C15 RE 72.6(2) . . ?
C12 C16 C15 108.5(5) . . ?
C12 C16 RE 72.9(2) . . ?
C15 C16 RE 71.4(3) . . ?
O1C C1C RE 178.1(5) . . ?
O2C C2C RE 178.0(5) . . ?
O3C C3C RE 176.1(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
O1 H1 O1C_$1 0.832(10) 2.350(15) 3.031(5) 140(2) 2_545
O10 H10 N9_$2 0.834(10) 2.119(16) 2.890(5) 153.7(16) 3_676

_refine_diff_density_max         1.771
_refine_diff_density_min         -0.895
_refine_diff_density_rms         0.136

####################################################################### 
# 
# 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_2058zs
_database_code_depnum_ccdc_archive 'CCDC 2064833'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2021-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N2 O5 Re'
_chemical_formula_weight         490.50

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.382(4)
_cell_length_b                   10.503(4)
_cell_length_c                   16.360(6)
_cell_angle_alpha                80.32(3)
_cell_angle_beta                 80.44(3)
_cell_angle_gamma                74.62(2)
_cell_volume                     1681.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3352
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      21.75

_exptl_crystal_description       plate
_exptl_crystal_colour            blue_violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_F_000             940
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    7.252
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2490
_exptl_absorpt_correction_T_max  0.4711
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26693
_diffrn_reflns_av_unetI/netI     0.2594
_diffrn_reflns_av_R_equivalents  0.4017
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.250
_diffrn_reflns_theta_max         28.471
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8295
_reflns_number_gt                3512
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0756P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8295
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1561
_refine_ls_R_factor_gt           0.0838
_refine_ls_wR_factor_ref         0.2349
_refine_ls_wR_factor_gt          0.1849
_refine_ls_goodness_of_fit_ref   0.839
_refine_ls_restrained_S_all      0.839
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Re2 Re 0.56354(5) 0.69376(6) 0.62412(4) 0.0462(2) Uani 1 1 d . . . . .
C21 C 0.3852(19) 0.740(2) 0.5883(9) 0.062(5) Uani 1 1 d . . . . .
O21 O 0.2801(13) 0.7632(19) 0.5708(9) 0.100(5) Uani 1 1 d . . . . .
O22 O 0.6544(15) 0.9027(15) 0.4856(9) 0.092(5) Uani 1 1 d . . . . .
C22 C 0.615(2) 0.826(2) 0.5378(12) 0.070(5) Uani 1 1 d . . . . .
C23 C 0.5025(14) 0.8240(17) 0.6962(10) 0.051(4) Uani 1 1 d . . . . .
O23 O 0.4682(12) 0.8964(13) 0.7469(9) 0.075(4) Uani 1 1 d . . . . .
O201 O 0.4053(13) 0.3635(17) 0.5954(9) 0.097(5) Uani 1 1 d . . . . .
N202 N 0.3708(12) 0.3867(13) 0.6721(9) 0.055(4) Uani 1 1 d . . . . .
C203 C 0.2481(14) 0.3544(18) 0.7242(11) 0.057(4) Uani 1 1 d . . . . .
C204 C 0.1296(15) 0.404(2) 0.6716(12) 0.077(6) Uani 1 1 d . . . . .
H20A H 0.049769 0.383627 0.704195 0.116 Uiso 1 1 calc R U . . .
H20B H 0.114515 0.498074 0.655649 0.116 Uiso 1 1 calc R U . . .
H20C H 0.150694 0.359661 0.622443 0.116 Uiso 1 1 calc R U . . .
C205 C 0.2775(17) 0.2042(18) 0.7418(14) 0.079(6) Uani 1 1 d . . . . .
H20D H 0.201178 0.178423 0.775291 0.119 Uiso 1 1 calc R U . . .
H20E H 0.295189 0.167546 0.689925 0.119 Uiso 1 1 calc R U . . .
H20F H 0.354851 0.171207 0.771223 0.119 Uiso 1 1 calc R U . . .
C206 C 0.2366(14) 0.4256(16) 0.8045(11) 0.051(4) Uani 1 1 d . . . . .
C207 C 0.2123(19) 0.349(3) 0.8861(12) 0.090(7) Uani 1 1 d . . . . .
H20G H 0.275742 0.263440 0.888482 0.135 Uiso 1 1 calc R U . . .
H20H H 0.222897 0.395741 0.929073 0.135 Uiso 1 1 calc R U . . .
H20I H 0.122435 0.336542 0.894314 0.135 Uiso 1 1 calc R U . . .
C208 C 0.1409(17) 0.558(2) 0.7983(15) 0.092(7) Uani 1 1 d . . . . .
H20J H 0.158951 0.606054 0.744216 0.138 Uiso 1 1 calc R U . . .
H20K H 0.050567 0.546763 0.805998 0.138 Uiso 1 1 calc R U . . .
H20L H 0.151029 0.605962 0.840758 0.138 Uiso 1 1 calc R U . . .
N209 N 0.3737(12) 0.4519(14) 0.7918(8) 0.053(3) Uani 1 1 d . . . . .
O210 O 0.4119(12) 0.5007(15) 0.8488(8) 0.085(5) Uani 1 1 d . . . . .
C211 C 0.4404(12) 0.4374(15) 0.7161(10) 0.044(4) Uani 1 1 d . . . . .
C212 C 0.5662(14) 0.4754(16) 0.6817(10) 0.050(4) Uani 1 1 d . . . . .
C213 C 0.6283(14) 0.4767(18) 0.5924(12) 0.059(5) Uani 1 1 d . . . . .
H21A H 0.599456 0.442484 0.548117 0.071 Uiso 1 1 calc R U . . .
C214 C 0.7442(16) 0.5300(18) 0.5860(13) 0.071(6) Uani 1 1 d . . . . .
H21B H 0.811206 0.536438 0.536656 0.085 Uiso 1 1 calc R U . . .
C215 C 0.7549(15) 0.5524(18) 0.6706(13) 0.069(5) Uani 1 1 d . . . . .
H21C H 0.829270 0.579407 0.687159 0.083 Uiso 1 1 calc R U . . .
C216 C 0.6464(15) 0.5239(17) 0.7228(11) 0.055(4) Uani 1 1 d . . . . .
H21D H 0.631115 0.529827 0.782924 0.066 Uiso 1 1 calc R U . . .
Re1 Re 0.87350(5) -0.03501(6) 0.70567(4) 0.0472(2) Uani 1 1 d . . . . .
C11 C 0.8278(18) -0.1714(19) 0.7906(12) 0.071(5) Uani 1 1 d . . . . .
O11 O 0.7920(16) -0.2529(18) 0.8418(11) 0.123(6) Uani 1 1 d . . . . .
C12 C 0.9318(14) -0.1598(18) 0.6308(10) 0.053(4) Uani 1 1 d . . . . .
O12 O 0.9673(13) -0.2326(15) 0.5805(9) 0.084(4) Uani 1 1 d . . . . .
O13 O 1.1556(13) -0.0966(16) 0.7585(9) 0.094(5) Uani 1 1 d . . . . .
C13 C 1.0505(15) -0.0789(18) 0.7372(11) 0.061(5) Uani 1 1 d . . . . .
O101 O 0.5399(11) 0.1180(15) 0.8894(8) 0.084(4) Uani 1 1 d . . . . .
N102 N 0.6401(10) 0.1613(13) 0.9010(8) 0.050(3) Uani 1 1 d . . . . .
C103 C 0.6668(14) 0.1754(18) 0.9859(10) 0.053(4) Uani 1 1 d . . . . .
C104 C 0.5335(17) 0.241(2) 1.0363(11) 0.074(6) Uani 1 1 d . . . . .
H10A H 0.550223 0.250519 1.090689 0.112 Uiso 1 1 calc R U . . .
H10B H 0.496635 0.327585 1.007535 0.112 Uiso 1 1 calc R U . . .
H10C H 0.470759 0.186739 1.041914 0.112 Uiso 1 1 calc R U . . .
C105 C 0.7184(19) 0.029(2) 1.0269(13) 0.080(6) Uani 1 1 d . . . . .
H10D H 0.738021 0.029654 1.082144 0.119 Uiso 1 1 calc R U . . .
H10E H 0.650247 -0.018404 1.030064 0.119 Uiso 1 1 calc R U . . .
H10F H 0.798564 -0.013144 0.993694 0.119 Uiso 1 1 calc R U . . .
C106 C 0.7750(14) 0.2545(17) 0.9655(9) 0.051(4) Uani 1 1 d . . . . .
C107 C 0.7090(17) 0.4024(16) 0.9607(9) 0.061(5) Uani 1 1 d . . . . .
H10G H 0.637623 0.424227 0.926429 0.091 Uiso 1 1 calc R U . . .
H10H H 0.672935 0.424473 1.015914 0.091 Uiso 1 1 calc R U . . .
H10I H 0.774768 0.451956 0.936803 0.091 Uiso 1 1 calc R U . . .
C108 C 0.8862(17) 0.214(2) 1.0176(12) 0.085(7) Uani 1 1 d . . . . .
H10J H 0.925162 0.120510 1.019049 0.128 Uiso 1 1 calc R U . . .
H10K H 0.953740 0.262180 0.994297 0.128 Uiso 1 1 calc R U . . .
H10L H 0.851907 0.234698 1.073408 0.128 Uiso 1 1 calc R U . . .
N109 N 0.8243(11) 0.2304(14) 0.8747(8) 0.052(3) Uani 1 1 d . . . . .
O110 O 0.9351(11) 0.2571(17) 0.8366(8) 0.097(5) Uani 1 1 d . . . . .
C111 C 0.7402(13) 0.1820(15) 0.8406(10) 0.044(4) Uani 1 1 d . . . . .
C112 C 0.7571(14) 0.1625(15) 0.7570(11) 0.052(4) Uani 1 1 d . . . . .
C113 C 0.6655(15) 0.1112(17) 0.7165(14) 0.069(5) Uani 1 1 d . . . . .
H11A H 0.581157 0.089309 0.743635 0.083 Uiso 1 1 calc R U . . .
C114 C 0.714(2) 0.1138(17) 0.6305(11) 0.064(5) Uani 1 1 d . . . . .
H11B H 0.669164 0.090738 0.588758 0.077 Uiso 1 1 calc R U . . .
C115 C 0.8315(19) 0.1632(19) 0.6123(11) 0.067(5) Uani 1 1 d . . . . .
H11C H 0.881310 0.181403 0.556997 0.080 Uiso 1 1 calc R U . . .
C116 C 0.8565(16) 0.1887(18) 0.6882(11) 0.057(4) Uani 1 1 d . . . . .
H11D H 0.930564 0.227187 0.693528 0.069 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
Re2 C23 1.870(17) . ?
Re2 C22 1.93(2) . ?
Re2 C21 1.948(18) . ?
Re2 C214 2.264(17) . ?
Re2 C216 2.282(16) . ?
Re2 C215 2.300(15) . ?
Re2 C212 2.323(16) . ?
Re2 C213 2.321(17) . ?
C21 O21 1.127(19) . ?
O22 C22 1.17(2) . ?
C23 O23 1.166(18) . ?
O201 N202 1.291(16) . ?
N202 C211 1.353(16) . ?
N202 C203 1.496(19) . ?
C203 C205 1.51(2) . ?
C203 C204 1.55(2) . ?
C203 C206 1.59(2) . ?
C206 C207 1.46(3) . ?
C206 C208 1.47(2) . ?
C206 N209 1.495(18) . ?
N209 O210 1.297(15) . ?
N209 C211 1.325(18) . ?
C211 C212 1.46(2) . ?
C212 C216 1.390(19) . ?
C212 C213 1.50(2) . ?
C213 C214 1.44(2) . ?
C214 C215 1.47(3) . ?
C215 C216 1.36(2) . ?
Re1 C12 1.860(17) . ?
Re1 C13 1.908(15) . ?
Re1 C11 1.92(2) . ?
Re1 C116 2.281(18) . ?
Re1 C113 2.293(15) . ?
Re1 C112 2.321(15) . ?
Re1 C114 2.315(16) . ?
Re1 C115 2.352(19) . ?
C11 O11 1.18(2) . ?
C12 O12 1.164(18) . ?
O13 C13 1.159(17) . ?
O101 N102 1.293(14) . ?
N102 C111 1.346(17) . ?
N102 C103 1.498(19) . ?
C103 C106 1.53(2) . ?
C103 C104 1.54(2) . ?
C103 C105 1.56(3) . ?
C106 C108 1.48(2) . ?
C106 C107 1.52(2) . ?
C106 N109 1.529(18) . ?
N109 O110 1.289(15) . ?
N109 C111 1.350(16) . ?
C111 C112 1.39(2) . ?
C112 C116 1.44(2) . ?
C112 C113 1.49(2) . ?
C113 C114 1.41(2) . ?
C114 C115 1.42(3) . ?
C115 C116 1.39(2) . ?

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
C23 Re2 C22 89.0(7) . . ?
C23 Re2 C21 89.3(7) . . ?
C22 Re2 C21 89.7(8) . . ?
C23 Re2 C214 142.5(6) . . ?
C22 Re2 C214 93.8(8) . . ?
C21 Re2 C214 128.1(7) . . ?
C23 Re2 C216 96.1(7) . . ?
C22 Re2 C216 142.6(7) . . ?
C21 Re2 C216 127.2(7) . . ?
C214 Re2 C216 60.7(7) . . ?
C23 Re2 C215 106.6(7) . . ?
C22 Re2 C215 108.7(8) . . ?
C21 Re2 C215 155.5(8) . . ?
C214 Re2 C215 37.5(7) . . ?
C216 Re2 C215 34.6(6) . . ?
C23 Re2 C212 117.1(6) . . ?
C22 Re2 C212 153.0(7) . . ?
C21 Re2 C212 97.2(7) . . ?
C214 Re2 C212 61.5(6) . . ?
C216 Re2 C212 35.1(5) . . ?
C215 Re2 C212 59.1(6) . . ?
C23 Re2 C213 154.4(7) . . ?
C22 Re2 C213 115.8(7) . . ?
C21 Re2 C213 97.1(7) . . ?
C214 Re2 C213 36.5(5) . . ?
C216 Re2 C213 60.5(6) . . ?
C215 Re2 C213 60.7(6) . . ?
C212 Re2 C213 37.6(6) . . ?
O21 C21 Re2 176.9(17) . . ?
O22 C22 Re2 176.1(19) . . ?
O23 C23 Re2 174.0(15) . . ?
O201 N202 C211 125.8(12) . . ?
O201 N202 C203 122.6(12) . . ?
C211 N202 C203 111.6(13) . . ?
N202 C203 C205 106.4(13) . . ?
N202 C203 C204 108.3(15) . . ?
C205 C203 C204 108.2(14) . . ?
N202 C203 C206 102.5(12) . . ?
C205 C203 C206 114.1(16) . . ?
C204 C203 C206 116.6(14) . . ?
C207 C206 C208 111.1(17) . . ?
C207 C206 N209 110.6(14) . . ?
C208 C206 N209 105.8(14) . . ?
C207 C206 C203 117.3(15) . . ?
C208 C206 C203 111.6(15) . . ?
N209 C206 C203 99.3(11) . . ?
O210 N209 C211 124.9(12) . . ?
O210 N209 C206 119.9(12) . . ?
C211 N209 C206 114.7(12) . . ?
N209 C211 N202 109.5(12) . . ?
N209 C211 C212 126.7(13) . . ?
N202 C211 C212 123.7(14) . . ?
C216 C212 C211 127.7(15) . . ?
C216 C212 C213 106.8(14) . . ?
C211 C212 C213 125.4(13) . . ?
C216 C212 Re2 70.8(9) . . ?
C211 C212 Re2 120.4(10) . . ?
C213 C212 Re2 71.1(9) . . ?
C214 C213 C212 106.1(14) . . ?
C214 C213 Re2 69.6(9) . . ?
C212 C213 Re2 71.3(9) . . ?
C213 C214 C215 106.9(16) . . ?
C213 C214 Re2 73.9(9) . . ?
C215 C214 Re2 72.5(9) . . ?
C216 C215 C214 108.3(15) . . ?
C216 C215 Re2 72.0(9) . . ?
C214 C215 Re2 69.9(9) . . ?
C215 C216 C212 111.8(16) . . ?
C215 C216 Re2 73.4(10) . . ?
C212 C216 Re2 74.1(9) . . ?
C12 Re1 C13 89.5(7) . . ?
C12 Re1 C11 89.2(8) . . ?
C13 Re1 C11 89.7(8) . . ?
C12 Re1 C116 131.5(7) . . ?
C13 Re1 C116 93.5(7) . . ?
C11 Re1 C116 139.1(6) . . ?
C12 Re1 C113 124.8(6) . . ?
C13 Re1 C113 145.0(7) . . ?
C11 Re1 C113 96.5(7) . . ?
C116 Re1 C113 60.0(6) . . ?
C12 Re1 C112 158.2(6) . . ?
C13 Re1 C112 107.3(7) . . ?
C11 Re1 C112 104.2(7) . . ?
C116 Re1 C112 36.4(5) . . ?
C113 Re1 C112 37.8(5) . . ?
C12 Re1 C114 97.4(6) . . ?
C13 Re1 C114 147.4(8) . . ?
C11 Re1 C114 122.0(8) . . ?
C116 Re1 C114 58.5(6) . . ?
C113 Re1 C114 35.7(6) . . ?
C112 Re1 C114 61.0(6) . . ?
C12 Re1 C115 100.4(7) . . ?
C13 Re1 C115 112.1(7) . . ?
C11 Re1 C115 156.0(7) . . ?
C116 Re1 C115 35.0(6) . . ?
C113 Re1 C115 59.9(7) . . ?
C112 Re1 C115 60.8(6) . . ?
C114 Re1 C115 35.4(6) . . ?
O11 C11 Re1 176.0(18) . . ?
O12 C12 Re1 176.5(16) . . ?
O13 C13 Re1 175.0(17) . . ?
O101 N102 C111 123.9(12) . . ?
O101 N102 C103 123.0(12) . . ?
C111 N102 C103 112.6(11) . . ?
N102 C103 C106 102.8(12) . . ?
N102 C103 C104 109.2(12) . . ?
C106 C103 C104 116.3(14) . . ?
N102 C103 C105 104.2(14) . . ?
C106 C103 C105 113.8(13) . . ?
C104 C103 C105 109.5(15) . . ?
C108 C106 C107 112.1(15) . . ?
C108 C106 C103 117.1(16) . . ?
C107 C106 C103 109.7(13) . . ?
C108 C106 N109 112.0(12) . . ?
C107 C106 N109 104.8(13) . . ?
C103 C106 N109 99.8(11) . . ?
O110 N109 C111 125.4(12) . . ?
O110 N109 C106 121.2(11) . . ?
C111 N109 C106 113.3(11) . . ?
N102 C111 N109 107.5(12) . . ?
N102 C111 C112 128.3(12) . . ?
N109 C111 C112 124.1(13) . . ?
C111 C112 C116 131.5(14) . . ?
C111 C112 C113 125.9(14) . . ?
C116 C112 C113 102.5(15) . . ?
C111 C112 Re1 124.5(11) . . ?
C116 C112 Re1 70.3(9) . . ?
C113 C112 Re1 70.1(8) . . ?
C114 C113 C112 108.0(15) . . ?
C114 C113 Re1 73.0(9) . . ?
C112 C113 Re1 72.1(8) . . ?
C113 C114 C115 110.2(14) . . ?
C113 C114 Re1 71.3(9) . . ?
C115 C114 Re1 73.7(10) . . ?
C116 C115 C114 105.9(17) . . ?
C116 C115 Re1 69.8(11) . . ?
C114 C115 Re1 70.9(11) . . ?
C115 C116 C112 113.3(15) . . ?
C115 C116 Re1 75.3(11) . . ?
C112 C116 Re1 73.3(10) . . ?

_refine_diff_density_max         3.010
_refine_diff_density_min         -3.068
_refine_diff_density_rms         0.329

####################################################################### 
# 
# 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_2058drs
_database_code_depnum_ccdc_archive 'CCDC 2064835'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2021-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N2 O5 Re'
_chemical_formula_weight         490.50

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'
Re Re -1.0185 7.2310 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   17.0007(3)
_cell_length_b                   10.2467(2)
_cell_length_c                   20.5719(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.4390(10)
_cell_angle_gamma                90
_cell_volume                     3358.04(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6742
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      22.81

_exptl_crystal_description       plate
_exptl_crystal_colour            dark_blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.940
_exptl_crystal_F_000             1880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    7.262
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1987
_exptl_absorpt_correction_T_max  0.4803
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31900
_diffrn_reflns_av_unetI/netI     0.1086
_diffrn_reflns_av_R_equivalents  0.1263
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.251
_diffrn_reflns_theta_max         28.327
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8308
_reflns_number_gt                4704
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0805P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8308
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1350
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   0.768
_refine_ls_restrained_S_all      0.768
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.70509(2) 0.98189(3) 0.59539(2) 0.04540(12) Uani 1 1 d . . . . .
O1CA O 0.5399(5) 1.1368(8) 0.5408(5) 0.099(3) Uani 1 1 d . . . . .
C1CA C 0.6010(7) 1.0761(10) 0.5610(6) 0.066(3) Uani 1 1 d . . . . .
O2CA O 0.6715(5) 0.8406(8) 0.4570(4) 0.094(3) Uani 1 1 d . . . . .
C2CA C 0.6822(6) 0.8938(9) 0.5088(6) 0.061(3) Uani 1 1 d . . . . .
O3CA O 0.6206(7) 0.7624(10) 0.6459(5) 0.136(4) Uani 1 1 d . . . . .
C3CA C 0.6529(6) 0.8458(11) 0.6253(5) 0.064(3) Uani 1 1 d . . . . .
O1A O 0.8532(6) 0.7472(8) 0.7590(4) 0.103(3) Uani 1 1 d . . . . .
N2A N 0.8816(5) 0.7303(7) 0.7095(4) 0.059(2) Uani 1 1 d . . . . .
C3A C 0.9218(6) 0.6036(8) 0.7015(5) 0.055(2) Uani 1 1 d . . . . .
C4A C 0.8658(10) 0.4910(11) 0.7058(7) 0.106(5) Uani 1 1 d . . . . .
H4AA H 0.891456 0.410031 0.700677 0.158 Uiso 1 1 calc R U . . .
H4AB H 0.858437 0.492703 0.749951 0.158 Uiso 1 1 calc R U . . .
H4AC H 0.812191 0.499122 0.669415 0.158 Uiso 1 1 calc R U . . .
C5A C 1.0051(8) 0.5980(11) 0.7613(6) 0.098(4) Uani 1 1 d . . . . .
H5AA H 1.033660 0.518393 0.758676 0.147 Uiso 1 1 calc R U . . .
H5AB H 1.039159 0.671108 0.758543 0.147 Uiso 1 1 calc R U . . .
H5AC H 0.995297 0.600949 0.804471 0.147 Uiso 1 1 calc R U . . .
C6A C 0.9308(7) 0.6262(8) 0.6284(5) 0.061(3) Uani 1 1 d . . . . .
C7A C 0.8598(11) 0.5657(13) 0.5689(6) 0.135(7) Uani 1 1 d . . . . .
H7AA H 0.807022 0.588176 0.573142 0.202 Uiso 1 1 calc R U . . .
H7AB H 0.861532 0.598184 0.525623 0.202 Uiso 1 1 calc R U . . .
H7AC H 0.866076 0.472516 0.570256 0.202 Uiso 1 1 calc R U . . .
C8A C 1.0147(10) 0.5937(13) 0.6239(9) 0.138(7) Uani 1 1 d . . . . .
H8AA H 1.058157 0.633104 0.662154 0.208 Uiso 1 1 calc R U . . .
H8AB H 1.022103 0.500676 0.625735 0.208 Uiso 1 1 calc R U . . .
H8AC H 1.017559 0.626343 0.581102 0.208 Uiso 1 1 calc R U . . .
N9A N 0.9165(5) 0.7696(7) 0.6204(4) 0.0551(19) Uani 1 1 d . . . . .
O10A O 0.9268(6) 0.8291(7) 0.5691(4) 0.104(3) Uani 1 1 d . . . . .
C11A C 0.8820(5) 0.8192(8) 0.6633(4) 0.0423(19) Uani 1 1 d . . . . .
C12A C 0.8449(5) 0.9515(8) 0.6575(4) 0.0435(19) Uani 1 1 d . . . . .
C13A C 0.8381(6) 1.0415(8) 0.6029(5) 0.055(2) Uani 1 1 d . . . . .
H13A H 0.862630 1.031219 0.566588 0.066 Uiso 1 1 calc R U . . .
C14A C 0.7988(6) 1.1538(9) 0.6160(6) 0.067(3) Uani 1 1 d . . . . .
H14A H 0.789902 1.235337 0.589530 0.081 Uiso 1 1 calc R U . . .
C15A C 0.7785(6) 1.1317(10) 0.6769(6) 0.068(3) Uani 1 1 d . . . . .
H15A H 0.753876 1.196022 0.699517 0.082 Uiso 1 1 calc R U . . .
C16A C 0.8077(6) 1.0071(9) 0.7028(5) 0.058(3) Uani 1 1 d . . . . .
H16A H 0.807449 0.969424 0.746521 0.070 Uiso 1 1 calc R U . . .
Re2 Re 0.38314(2) 0.58958(3) 0.60009(2) 0.04265(12) Uani 1 1 d . . . . .
O1CB O 0.3476(6) 0.5838(8) 0.4441(4) 0.096(3) Uani 1 1 d . . . . .
C1CB C 0.3601(7) 0.5874(9) 0.5018(5) 0.060(3) Uani 1 1 d . . . . .
O2CB O 0.1969(5) 0.5953(8) 0.5805(5) 0.099(3) Uani 1 1 d . . . . .
C2CB C 0.2685(8) 0.5972(9) 0.5860(5) 0.067(3) Uani 1 1 d . . . . .
O3CB O 0.3934(6) 0.8868(7) 0.6043(4) 0.102(3) Uani 1 1 d . . . . .
C3CB C 0.3878(6) 0.7771(10) 0.6002(5) 0.069(3) Uani 1 1 d . . . . .
O1B O 0.3458(5) 0.3424(6) 0.7756(4) 0.0712(19) Uani 1 1 d . . . . .
N2B N 0.3637(4) 0.4612(6) 0.7934(3) 0.0443(16) Uani 1 1 d . . . . .
C3B C 0.3292(6) 0.5288(8) 0.8420(4) 0.046(2) Uani 1 1 d . . . . .
C4B C 0.3371(8) 0.4402(10) 0.9032(6) 0.080(3) Uani 1 1 d . . . . .
H4BA H 0.395323 0.423674 0.928718 0.120 Uiso 1 1 calc R U . . .
H4BB H 0.311979 0.481804 0.933012 0.120 Uiso 1 1 calc R U . . .
H4BC H 0.308885 0.359144 0.886636 0.120 Uiso 1 1 calc R U . . .
C5B C 0.3844(6) 0.6535(9) 0.8602(4) 0.050(2) Uani 1 1 d . . . . .
C5BZ C 0.2371(6) 0.5552(10) 0.8015(6) 0.067(3) Uani 1 1 d . . . . .
H5BA H 0.212278 0.598820 0.830876 0.101 Uiso 1 1 calc R U . . .
H5BB H 0.232318 0.609488 0.762241 0.101 Uiso 1 1 calc R U . . .
H5BC H 0.208579 0.474109 0.785759 0.101 Uiso 1 1 calc R U . . .
C6B C 0.3388(7) 0.7790(9) 0.8651(5) 0.068(3) Uani 1 1 d . . . . .
H6BA H 0.320555 0.774132 0.904250 0.101 Uiso 1 1 calc R U . . .
H6BB H 0.376201 0.851783 0.870767 0.101 Uiso 1 1 calc R U . . .
H6BC H 0.291028 0.790190 0.823477 0.101 Uiso 1 1 calc R U . . .
C7B C 0.4652(6) 0.6416(11) 0.9232(5) 0.069(3) Uani 1 1 d . . . . .
H7BA H 0.493766 0.562380 0.919908 0.103 Uiso 1 1 calc R U . . .
H7BB H 0.500946 0.714878 0.924553 0.103 Uiso 1 1 calc R U . . .
H7BC H 0.451743 0.640029 0.964810 0.103 Uiso 1 1 calc R U . . .
N9B N 0.4134(5) 0.6604(6) 0.7988(4) 0.0506(18) Uani 1 1 d . . . . .
O10B O 0.4491(5) 0.7610(6) 0.7841(3) 0.078(2) Uani 1 1 d . . . . .
C11B C 0.4056(5) 0.5430(7) 0.7664(4) 0.0414(19) Uani 1 1 d . . . . .
C12B C 0.4366(6) 0.5109(7) 0.7111(4) 0.047(2) Uani 1 1 d . . . . .
C13B C 0.5035(5) 0.5755(8) 0.6963(4) 0.048(2) Uani 1 1 d . . . . .
H13B H 0.537080 0.648825 0.722106 0.058 Uiso 1 1 calc R U . . .
C14B C 0.5167(6) 0.5064(9) 0.6417(5) 0.055(2) Uani 1 1 d . . . . .
H14B H 0.560788 0.526222 0.622692 0.066 Uiso 1 1 calc R U . . .
C15B C 0.4605(7) 0.3994(8) 0.6210(5) 0.060(3) Uani 1 1 d . . . . .
H15B H 0.459733 0.332055 0.586909 0.072 Uiso 1 1 calc R U . . .
C16B C 0.4101(6) 0.4017(7) 0.6656(4) 0.052(2) Uani 1 1 d . . . . .
H16C H 0.368550 0.336122 0.666570 0.063 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 C3CA 1.869(11) . ?
Re1 C1CA 1.921(12) . ?
Re1 C2CA 1.911(11) . ?
Re1 C12A 2.293(8) . ?
Re1 C16A 2.303(9) . ?
Re1 C15A 2.295(8) . ?
Re1 C13A 2.295(9) . ?
Re1 C14A 2.313(9) . ?
O1CA C1CA 1.156(12) . ?
O2CA C2CA 1.154(11) . ?
O3CA C3CA 1.173(11) . ?
O1A N2A 1.282(9) . ?
N2A C11A 1.318(10) . ?
N2A C3A 1.502(11) . ?
C3A C4A 1.518(13) . ?
C3A C5A 1.519(15) . ?
C3A C6A 1.581(13) . ?
C6A C7A 1.519(17) . ?
C6A C8A 1.498(16) . ?
C6A N9A 1.490(11) . ?
N9A O10A 1.281(8) . ?
N9A C11A 1.321(10) . ?
C11A C12A 1.483(11) . ?
C12A C13A 1.426(12) . ?
C12A C16A 1.416(11) . ?
C13A C14A 1.403(12) . ?
C14A C15A 1.430(14) . ?
C15A C16A 1.406(14) . ?
Re2 C2CB 1.870(12) . ?
Re2 C3CB 1.923(11) . ?
Re2 C1CB 1.920(10) . ?
Re2 C13B 2.302(8) . ?
Re2 C14B 2.293(9) . ?
Re2 C12B 2.289(8) . ?
Re2 C16B 2.302(7) . ?
Re2 C15B 2.306(8) . ?
O1CB C1CB 1.131(10) . ?
O2CB C2CB 1.182(12) . ?
O3CB C3CB 1.130(11) . ?
O1B N2B 1.277(8) . ?
N2B C11B 1.339(10) . ?
N2B C3B 1.494(10) . ?
C3B C5BZ 1.519(12) . ?
C3B C4B 1.520(12) . ?
C3B C5B 1.552(12) . ?
C5B C6B 1.523(12) . ?
C5B N9B 1.509(10) . ?
C5B C7B 1.530(12) . ?
N9B O10B 1.285(8) . ?
N9B C11B 1.358(10) . ?
C11B C12B 1.450(11) . ?
C12B C16B 1.427(11) . ?
C12B C13B 1.438(12) . ?
C13B C14B 1.411(11) . ?
C14B C15B 1.419(13) . ?
C15B C16B 1.458(13) . ?

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
C3CA Re1 C1CA 90.8(4) . . ?
C3CA Re1 C2CA 89.3(4) . . ?
C1CA Re1 C2CA 91.9(4) . . ?
C3CA Re1 C12A 103.6(4) . . ?
C1CA Re1 C12A 156.3(4) . . ?
C2CA Re1 C12A 106.8(4) . . ?
C3CA Re1 C16A 93.2(4) . . ?
C1CA Re1 C16A 126.1(4) . . ?
C2CA Re1 C16A 141.9(4) . . ?
C12A Re1 C16A 35.9(3) . . ?
C3CA Re1 C15A 117.3(4) . . ?
C1CA Re1 C15A 97.4(4) . . ?
C2CA Re1 C15A 151.5(4) . . ?
C12A Re1 C15A 59.4(3) . . ?
C16A Re1 C15A 35.6(3) . . ?
C3CA Re1 C13A 138.3(4) . . ?
C1CA Re1 C13A 130.6(4) . . ?
C2CA Re1 C13A 93.7(4) . . ?
C12A Re1 C13A 36.2(3) . . ?
C16A Re1 C13A 60.5(4) . . ?
C15A Re1 C13A 60.1(3) . . ?
C3CA Re1 C14A 152.1(4) . . ?
C1CA Re1 C14A 99.9(4) . . ?
C2CA Re1 C14A 115.7(4) . . ?
C12A Re1 C14A 59.2(3) . . ?
C16A Re1 C14A 59.7(4) . . ?
C15A Re1 C14A 36.1(4) . . ?
C13A Re1 C14A 35.5(3) . . ?
O1CA C1CA Re1 177.7(10) . . ?
O2CA C2CA Re1 177.5(9) . . ?
O3CA C3CA Re1 177.9(9) . . ?
O1A N2A C11A 125.2(8) . . ?
O1A N2A C3A 121.1(7) . . ?
C11A N2A C3A 113.7(7) . . ?
N2A C3A C4A 109.4(9) . . ?
N2A C3A C5A 106.0(8) . . ?
C4A C3A C5A 110.5(9) . . ?
N2A C3A C6A 100.2(7) . . ?
C4A C3A C6A 115.9(8) . . ?
C5A C3A C6A 113.8(9) . . ?
C7A C6A C8A 111.4(11) . . ?
C7A C6A N9A 105.1(10) . . ?
C8A C6A N9A 109.5(8) . . ?
C7A C6A C3A 113.2(9) . . ?
C8A C6A C3A 115.9(10) . . ?
N9A C6A C3A 100.6(7) . . ?
O10A N9A C11A 126.0(7) . . ?
O10A N9A C6A 119.8(7) . . ?
C11A N9A C6A 113.4(7) . . ?
N2A C11A N9A 109.4(7) . . ?
N2A C11A C12A 125.5(7) . . ?
N9A C11A C12A 125.0(7) . . ?
C13A C12A C16A 109.1(8) . . ?
C13A C12A C11A 124.7(7) . . ?
C16A C12A C11A 126.2(8) . . ?
C13A C12A Re1 72.0(5) . . ?
C16A C12A Re1 72.4(5) . . ?
C11A C12A Re1 119.8(6) . . ?
C14A C13A C12A 106.9(9) . . ?
C14A C13A Re1 73.0(5) . . ?
C12A C13A Re1 71.8(5) . . ?
C13A C14A C15A 108.4(9) . . ?
C13A C14A Re1 71.5(5) . . ?
C15A C14A Re1 71.2(5) . . ?
C16A C15A C14A 108.3(8) . . ?
C16A C15A Re1 72.5(5) . . ?
C14A C15A Re1 72.6(5) . . ?
C15A C16A C12A 107.2(9) . . ?
C15A C16A Re1 71.9(5) . . ?
C12A C16A Re1 71.7(5) . . ?
C2CB Re2 C3CB 89.9(4) . . ?
C2CB Re2 C1CB 91.1(4) . . ?
C3CB Re2 C1CB 90.3(4) . . ?
C2CB Re2 C13B 134.6(4) . . ?
C3CB Re2 C13B 92.2(4) . . ?
C1CB Re2 C13B 134.2(4) . . ?
C2CB Re2 C14B 156.4(4) . . ?
C3CB Re2 C14B 109.7(4) . . ?
C1CB Re2 C14B 101.5(4) . . ?
C13B Re2 C14B 35.8(3) . . ?
C2CB Re2 C12B 101.4(4) . . ?
C3CB Re2 C12B 110.4(3) . . ?
C1CB Re2 C12B 155.5(3) . . ?
C13B Re2 C12B 36.5(3) . . ?
C14B Re2 C12B 60.0(3) . . ?
C2CB Re2 C16B 96.3(4) . . ?
C3CB Re2 C16B 146.7(4) . . ?
C1CB Re2 C16B 122.1(3) . . ?
C13B Re2 C16B 60.6(3) . . ?
C14B Re2 C16B 60.1(3) . . ?
C12B Re2 C16B 36.2(3) . . ?
C2CB Re2 C15B 124.0(4) . . ?
C3CB Re2 C15B 145.5(4) . . ?
C1CB Re2 C15B 94.6(4) . . ?
C13B Re2 C15B 60.6(3) . . ?
C14B Re2 C15B 35.9(3) . . ?
C12B Re2 C15B 61.0(3) . . ?
C16B Re2 C15B 36.9(3) . . ?
O1CB C1CB Re2 178.5(9) . . ?
O2CB C2CB Re2 175.4(10) . . ?
O3CB C3CB Re2 175.9(9) . . ?
O1B N2B C11B 125.9(7) . . ?
O1B N2B C3B 121.6(7) . . ?
C11B N2B C3B 112.2(6) . . ?
C5BZ C3B N2B 106.6(7) . . ?
C5BZ C3B C4B 109.7(8) . . ?
N2B C3B C4B 109.6(7) . . ?
C5BZ C3B C5B 114.0(7) . . ?
N2B C3B C5B 101.3(6) . . ?
C4B C3B C5B 114.9(8) . . ?
C6B C5B N9B 109.8(7) . . ?
C6B C5B C3B 115.6(7) . . ?
N9B C5B C3B 100.6(6) . . ?
C6B C5B C7B 109.8(8) . . ?
N9B C5B C7B 104.7(7) . . ?
C3B C5B C7B 115.3(8) . . ?
O10B N9B C11B 124.7(7) . . ?
O10B N9B C5B 123.6(7) . . ?
C11B N9B C5B 111.4(7) . . ?
N2B C11B N9B 109.0(7) . . ?
N2B C11B C12B 125.1(7) . . ?
N9B C11B C12B 125.9(7) . . ?
C16B C12B C13B 108.3(8) . . ?
C16B C12B C11B 125.1(8) . . ?
C13B C12B C11B 126.4(8) . . ?
C16B C12B Re2 72.4(5) . . ?
C13B C12B Re2 72.2(5) . . ?
C11B C12B Re2 125.2(6) . . ?
C14B C13B C12B 107.1(8) . . ?
C14B C13B Re2 71.8(5) . . ?
C12B C13B Re2 71.3(5) . . ?
C15B C14B C13B 110.5(8) . . ?
C15B C14B Re2 72.5(5) . . ?
C13B C14B Re2 72.5(5) . . ?
C14B C15B C16B 106.3(8) . . ?
C14B C15B Re2 71.5(5) . . ?
C16B C15B Re2 71.4(4) . . ?
C12B C16B C15B 107.8(8) . . ?
C12B C16B Re2 71.4(4) . . ?
C15B C16B Re2 71.7(4) . . ?

_refine_diff_density_max         1.715
_refine_diff_density_min         -1.157
_refine_diff_density_rms         0.206

####################################################################### 
# 
# 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_2058s1
_database_code_depnum_ccdc_archive 'CCDC 2064832'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2021-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N2 O5 Re'
_chemical_formula_weight         490.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   11.8875(4)
_cell_length_b                   10.0482(3)
_cell_length_c                   14.1283(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.488(2)
_cell_angle_gamma                90
_cell_volume                     1686.01(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3715
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      22.53

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.932
_exptl_crystal_F_000             940
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    7.232
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1513
_exptl_absorpt_correction_T_max  0.3823
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15336
_diffrn_reflns_av_unetI/netI     0.0984
_diffrn_reflns_av_R_equivalents  0.0882
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.715
_diffrn_reflns_theta_max         28.375
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4179
_reflns_number_gt                1825
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0039(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4179
_refine_ls_number_parameters     211
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Re Re 0.33495(3) 0.74861(3) 0.53924(2) 0.05367(19) Uani 1 1 d . . . . .
O1C O 0.4114(7) 0.9526(7) 0.3982(5) 0.137(3) Uani 1 1 d . . . . .
C1C C 0.3810(9) 0.8740(10) 0.4502(7) 0.098(4) Uani 1 1 d . . . . .
O1B O 0.1048(6) 0.8747(7) 0.5270(5) 0.122(3) Uani 1 1 d . . . . .
C1B C 0.1925(9) 0.8262(11) 0.5292(7) 0.088(3) Uani 1 1 d . . . . .
O1A O 0.2704(6) 0.5511(7) 0.3805(5) 0.098(2) Uani 1 1 d . . . . .
C1A C 0.2949(7) 0.6292(9) 0.4410(7) 0.062(3) Uani 1 1 d . . . . .
O1R O 0.1402(6) 0.5992(6) 0.7568(6) 0.148(4) Uani 1 1 d . . . . .
N2R N 0.1794(6) 0.4993(7) 0.7167(5) 0.075(2) Uani 1 1 d . . . . .
C3R C 0.1218(9) 0.3698(10) 0.7147(8) 0.101(4) Uani 1 1 d . . . . .
C4R C 0.1277(13) 0.3227(16) 0.8204(11) 0.059(4) Uani 0.5 1 d . U P . .
H4RA H 0.205036 0.313468 0.841908 0.089 Uiso 0.5 1 calc R U P . .
H4RB H 0.091497 0.387280 0.858906 0.089 Uiso 0.5 1 calc R U P . .
H4RC H 0.090185 0.238561 0.825339 0.089 Uiso 0.5 1 calc R U P . .
C5R C 0.0082(12) 0.3798(13) 0.6913(10) 0.190(6) Uani 1 1 d . U . . .
H5RA H -0.025034 0.292757 0.691003 0.285 Uiso 1 1 calc R U . . .
H5RB H -0.027158 0.434686 0.736965 0.285 Uiso 1 1 calc R U . . .
H5RC H -0.002107 0.418957 0.629513 0.285 Uiso 1 1 calc R U . . .
C6R C 0.1956(11) 0.2887(11) 0.6572(9) 0.100(4) Uani 1 1 d . . . . .
C7R C 0.2396(13) 0.1568(16) 0.6943(10) 0.196(7) Uani 1 1 d . U . . .
H7RA H 0.177526 0.097957 0.703982 0.294 Uiso 1 1 calc R U . . .
H7RB H 0.288129 0.118207 0.649195 0.294 Uiso 1 1 calc R U . . .
H7RC H 0.281084 0.170457 0.753322 0.294 Uiso 1 1 calc R U . . .
C8R C 0.1599(19) 0.2647(12) 0.5478(16) 0.226(9) Uani 1 1 d . U . . .
H8RA H 0.094433 0.208854 0.543142 0.339 Uiso 1 1 calc R U . . .
H8RB H 0.143377 0.348650 0.517835 0.339 Uiso 1 1 calc R U . . .
H8RC H 0.220694 0.222313 0.516837 0.339 Uiso 1 1 calc R U . . .
N9R N 0.2960(7) 0.3756(8) 0.6437(6) 0.090(3) Uani 1 1 d . . . . .
O10R O 0.3812(7) 0.3376(7) 0.5980(6) 0.148(3) Uani 1 1 d . . . . .
C12R C 0.3531(7) 0.6050(8) 0.6647(6) 0.058(2) Uani 1 1 d . . . . .
C13R C 0.4583(7) 0.6062(9) 0.6159(6) 0.072(3) Uani 1 1 d . . . . .
H13A H 0.493722 0.528598 0.587427 0.086 Uiso 1 1 calc R U . . .
C14R C 0.5057(9) 0.7336(11) 0.6239(8) 0.085(3) Uani 1 1 d . . . . .
H14A H 0.578662 0.759442 0.599833 0.102 Uiso 1 1 calc R U . . .
C15R C 0.4335(10) 0.8197(11) 0.6759(8) 0.100(4) Uani 1 1 d . . . . .
H15A H 0.448826 0.911954 0.694993 0.120 Uiso 1 1 calc R U . . .
C16R C 0.3381(9) 0.7374(9) 0.7024(6) 0.076(3) Uani 1 1 d . . . . .
H16A H 0.277225 0.765520 0.742583 0.092 Uiso 1 1 calc R U . . .
C11R C 0.2767(7) 0.4964(8) 0.6768(6) 0.051(2) Uani 1 1 d . . . . .


_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
Re C1A 1.880(11) . ?
Re C1B 1.864(11) . ?
Re C1C 1.879(10) . ?
Re C12R 2.288(8) . ?
Re C16R 2.307(9) . ?
Re C13R 2.288(9) . ?
Re C14R 2.316(10) . ?
Re C15R 2.327(10) . ?
O1C C1C 1.147(9) . ?
O1B C1B 1.151(9) . ?
O1A C1A 1.187(9) . ?
O1R N2R 1.253(7) . ?
N2R C11R 1.309(8) . ?
N2R C3R 1.470(10) . ?
C3R C5R 1.380(14) . ?
C3R C6R 1.468(14) . ?
C3R C4R 1.566(16) . ?
C6R N9R 1.497(12) . ?
C6R C7R 1.510(17) . ?
C6R C8R 1.60(2) . ?
N9R O10R 1.283(8) . ?
N9R C11R 1.325(9) . ?
C12R C11R 1.434(9) . ?
C12R C16R 1.448(9) . ?
C12R C13R 1.454(10) . ?
C13R C14R 1.402(10) . ?
C14R C15R 1.443(14) . ?
C15R C16R 1.466(13) . ?

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
C1A Re C1B 90.6(4) . . ?
C1A Re C1C 90.3(4) . . ?
C1B Re C1C 87.6(5) . . ?
C1A Re C12R 100.5(3) . . ?
C1B Re C12R 112.2(4) . . ?
C1C Re C12R 157.1(4) . . ?
C1A Re C16R 134.4(3) . . ?
C1B Re C16R 94.1(4) . . ?
C1C Re C16R 135.2(4) . . ?
C12R Re C16R 36.7(2) . . ?
C1A Re C13R 95.0(3) . . ?
C1B Re C13R 149.2(4) . . ?
C1C Re C13R 122.5(4) . . ?
C12R Re C13R 37.1(3) . . ?
C16R Re C13R 61.0(3) . . ?
C1A Re C14R 121.9(4) . . ?
C1B Re C14R 147.1(4) . . ?
C1C Re C14R 96.6(4) . . ?
C12R Re C14R 60.5(3) . . ?
C16R Re C14R 60.3(4) . . ?
C13R Re C14R 35.4(3) . . ?
C1A Re C15R 155.6(4) . . ?
C1B Re C15R 110.9(5) . . ?
C1C Re C15R 101.5(4) . . ?
C12R Re C15R 61.6(3) . . ?
C16R Re C15R 36.9(3) . . ?
C13R Re C15R 60.7(4) . . ?
C14R Re C15R 36.2(4) . . ?
O1C C1C Re 177.7(10) . . ?
O1B C1B Re 177.2(10) . . ?
O1A C1A Re 178.3(8) . . ?
O1R N2R C11R 124.5(7) . . ?
O1R N2R C3R 122.4(7) . . ?
C11R N2R C3R 113.1(7) . . ?
C5R C3R N2R 113.0(11) . . ?
C5R C3R C6R 120.6(12) . . ?
N2R C3R C6R 102.3(8) . . ?
C5R C3R C4R 104.7(10) . . ?
N2R C3R C4R 104.3(10) . . ?
C6R C3R C4R 110.9(11) . . ?
N9R C6R C3R 104.2(9) . . ?
N9R C6R C7R 106.8(10) . . ?
C3R C6R C7R 120.1(11) . . ?
N9R C6R C8R 98.2(10) . . ?
C3R C6R C8R 118.5(12) . . ?
C7R C6R C8R 106.0(11) . . ?
O10R N9R C11R 127.1(8) . . ?
O10R N9R C6R 122.8(9) . . ?
C11R N9R C6R 109.8(8) . . ?
C11R C12R C16R 124.5(8) . . ?
C11R C12R C13R 128.7(8) . . ?
C16R C12R C13R 106.9(7) . . ?
C11R C12R Re 122.2(6) . . ?
C16R C12R Re 72.3(5) . . ?
C13R C12R Re 71.5(5) . . ?
C14R C13R C12R 108.7(8) . . ?
C14R C13R Re 73.4(6) . . ?
C12R C13R Re 71.5(5) . . ?
C13R C14R C15R 110.1(9) . . ?
C13R C14R Re 71.2(6) . . ?
C15R C14R Re 72.3(6) . . ?
C14R C15R C16R 106.0(9) . . ?
C14R C15R Re 71.5(6) . . ?
C16R C15R Re 70.8(5) . . ?
C12R C16R C15R 108.4(9) . . ?
C12R C16R Re 70.9(5) . . ?
C15R C16R Re 72.3(5) . . ?
N2R C11R N9R 110.0(7) . . ?
N2R C11R C12R 127.6(8) . . ?
N9R C11R C12R 122.4(8) . . ?

_refine_diff_density_max         0.985
_refine_diff_density_min         -0.892
_refine_diff_density_rms         0.178

####################################################################### 
# 
# 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_2095IN
_database_code_depnum_ccdc_archive 'CCDC 2064831'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2021-05-17 deposited with the CCDC.	2021-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N2 O4 Re'
_chemical_formula_weight         474.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -5.2083 5.8923 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   6.8520(3)
_cell_length_b                   24.5256(9)
_cell_length_c                   10.3668(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.5227(17)
_cell_angle_gamma                90
_cell_volume                     1651.89(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    240(2)
_cell_measurement_reflns_used    7419
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      67.91

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.908
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    14.558
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3741
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_process_details   SADABS-2012/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      240(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13367
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.847
_diffrn_reflns_theta_max         67.915
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2978
_reflns_number_gt                2749
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0618P)²+1.5391P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00055(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2978
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
RE Re 0.56350(3) 0.56906(2) 0.82240(2) 0.03877(15) Uani 1 1 d . . . . .
O1 O -0.0228(9) 0.5750(2) 0.4927(7) 0.0632(16) Uani 0.773(7) 1 d . . P A 1
O1B O 0.535(3) 0.6656(7) 0.519(2) 0.0632(16) Uani 0.227(7) 1 d . . P A 2
N2 N 0.0903(7) 0.60832(17) 0.4689(5) 0.0450(10) Uani 1 1 d . . . . .
C3 C 0.0258(9) 0.6644(2) 0.4139(6) 0.0463(12) Uani 1 1 d . . . . .
C4 C -0.0053(15) 0.6964(3) 0.5336(8) 0.079(2) Uani 1 1 d . . . . .
H4A H -0.030077 0.734482 0.508668 0.118 Uiso 1 1 calc R U . . .
H4AB H 0.117100 0.693195 0.612359 0.118 Uiso 1 1 calc R U . . .
H4AC H -0.122515 0.681627 0.555247 0.118 Uiso 1 1 calc R U . . .
C5 C -0.1789(10) 0.6614(3) 0.2993(7) 0.0671(17) Uani 1 1 d . . . . .
H5A H -0.211687 0.696922 0.256834 0.101 Uiso 1 1 calc R U . . .
H5AB H -0.286516 0.650393 0.336150 0.101 Uiso 1 1 calc R U . . .
H5AC H -0.168775 0.634960 0.232154 0.101 Uiso 1 1 calc R U . . .
C6 C 0.2188(10) 0.6807(2) 0.3765(6) 0.0544(13) Uani 1 1 d . . . . .
C7 C 0.2012(11) 0.6658(3) 0.2303(7) 0.0654(17) Uani 1 1 d . . . . .
H7A H 0.097153 0.688471 0.168063 0.098 Uiso 1 1 calc R U . . .
H7AB H 0.162713 0.627769 0.214004 0.098 Uiso 1 1 calc R U . . .
H7AC H 0.332680 0.671801 0.215806 0.098 Uiso 1 1 calc R U . . .
C8 C 0.2794(15) 0.7407(3) 0.4015(9) 0.094(3) Uani 1 1 d . . . . .
H8A H 0.399871 0.747806 0.374232 0.141 Uiso 1 1 calc R U . . .
H8AB H 0.310224 0.748926 0.497476 0.141 Uiso 1 1 calc R U . . .
H8AC H 0.166348 0.763455 0.348798 0.141 Uiso 1 1 calc R U . . .
N9 N 0.3874(8) 0.6454(2) 0.4635(6) 0.0635(14) Uani 1 1 d . . . . .
C10 C 0.3024(8) 0.6051(2) 0.5077(5) 0.0442(11) Uani 1 1 d . . . . .
C11 C 0.4156(9) 0.5608(2) 0.5914(5) 0.0395(10) Uani 1 1 d . . . . .
C12 C 0.3395(9) 0.5174(2) 0.6543(5) 0.0457(11) Uani 1 1 d . . . . .
H12 H 0.193250 0.510144 0.644087 0.055 Uiso 1 1 calc R U . . .
C13 C 0.5096(10) 0.4840(2) 0.7246(6) 0.0513(13) Uani 1 1 d . . . . .
H13 H 0.501866 0.449427 0.772130 0.062 Uiso 1 1 calc R U . . .
C14 C 0.6888(10) 0.5056(2) 0.7032(6) 0.0536(13) Uani 1 1 d . . . . .
H14 H 0.827596 0.488999 0.733876 0.064 Uiso 1 1 calc R U . . .
C15 C 0.6315(9) 0.5529(2) 0.6225(5) 0.0463(11) Uani 1 1 d . . . . .
H15 H 0.723725 0.574958 0.586574 0.056 Uiso 1 1 calc R U . . .
C1C C 0.3614(11) 0.5910(3) 0.9008(7) 0.0635(15) Uani 1 1 d . . . . .
O2C O 0.2310(10) 0.6030(3) 0.9443(7) 0.108(2) Uani 1 1 d . . . . .
C3C C 0.6740(11) 0.6413(3) 0.8425(7) 0.0632(15) Uani 1 1 d . . . . .
O4C O 0.7391(11) 0.6842(2) 0.8484(8) 0.110(2) Uani 1 1 d . . . . .
C5C C 0.7431(10) 0.5509(3) 0.9986(6) 0.0544(13) Uani 1 1 d . . . . .
O6C O 0.8542(8) 0.5380(2) 1.1041(5) 0.0794(14) Uani 1 1 d . . . . .


_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
RE C1C 1.893(7) . ?
RE C5C 1.903(6) . ?
RE C3C 1.911(6) . ?
RE C11 2.294(5) . ?
RE C13 2.298(5) . ?
RE C15 2.298(5) . ?
RE C12 2.302(5) . ?
RE C14 2.315(5) . ?
O1a N2 1.205(6) . ?
O1Bb N9 1.107(19) . ?
N2 C10 1.381(7) . ?
N2 C3 1.500(6) . ?
C3 C5 1.525(8) . ?
C3 C4 1.539(8) . ?
C3 C6 1.544(8) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C4 H4AC 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5AB 0.9700 . ?
C5 H5AC 0.9700 . ?
C6 N9 1.495(8) . ?
C6 C7 1.526(9) . ?
C6 C8 1.530(8) . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C7 H7AC 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C8 H8AC 0.9700 . ?
N9 C10 1.301(7) . ?
C10 C11 1.451(7) . ?
C11 C15 1.423(8) . ?
C11 C12 1.431(7) . ?
C12 C13 1.422(8) . ?
C12 H12 0.9900 . ?
C13 C14 1.418(9) . ?
C13 H13 0.9900 . ?
C14 C15 1.411(8) . ?
C14 H14 0.9900 . ?
C15 H15 0.9900 . ?
C1C O2C 1.159(8) . ?
C3C O4C 1.138(8) . ?
C5C O6C 1.161(8) . ?

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
C1C RE C5C 89.6(3) . . ?
C1C RE C3C 90.5(3) . . ?
C5C RE C3C 90.0(3) . . ?
C1C RE C11 109.4(3) . . ?
C5C RE C11 156.7(2) . . ?
C3C RE C11 102.9(2) . . ?
C1C RE C13 114.3(3) . . ?
C5C RE C13 100.1(2) . . ?
C3C RE C13 153.1(3) . . ?
C11 RE C13 60.25(19) . . ?
C1C RE C15 145.3(3) . . ?
C5C RE C15 124.8(2) . . ?
C3C RE C15 94.1(3) . . ?
C11 RE C15 36.1(2) . . ?
C13 RE C15 59.7(2) . . ?
C1C RE C12 94.5(3) . . ?
C5C RE C12 132.1(2) . . ?
C3C RE C12 137.6(2) . . ?
C11 RE C12 36.29(18) . . ?
C13 RE C12 36.0(2) . . ?
C15 RE C12 60.0(2) . . ?
C1C RE C14 150.0(3) . . ?
C5C RE C14 96.8(2) . . ?
C3C RE C14 118.7(3) . . ?
C11 RE C14 60.0(2) . . ?
C13 RE C14 35.8(2) . . ?
C15 RE C14 35.6(2) . . ?
C12 RE C14 59.8(2) . . ?
O1a N2 C10 126.0(5) . . ?
O1a N2 C3 124.7(5) . . ?
C10 N2 C3 108.6(4) . . ?
N2 C3 C5 109.8(5) . . ?
N2 C3 C4 105.1(5) . . ?
C5 C3 C4 108.9(6) . . ?
N2 C3 C6 99.2(4) . . ?
C5 C3 C6 117.8(5) . . ?
C4 C3 C6 114.8(6) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4AB 109.5 . . ?
H4A C4 H4AB 109.5 . . ?
C3 C4 H4AC 109.5 . . ?
H4A C4 H4AC 109.5 . . ?
H4AB C4 H4AC 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5AB 109.5 . . ?
H5A C5 H5AB 109.5 . . ?
C3 C5 H5AC 109.5 . . ?
H5A C5 H5AC 109.5 . . ?
H5AB C5 H5AC 109.5 . . ?
N9 C6 C7 105.3(5) . . ?
N9 C6 C8 109.8(6) . . ?
C7 C6 C8 109.3(5) . . ?
N9 C6 C3 105.0(4) . . ?
C7 C6 C3 112.6(5) . . ?
C8 C6 C3 114.4(6) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7AB 109.5 . . ?
H7A C7 H7AB 109.5 . . ?
C6 C7 H7AC 109.5 . . ?
H7A C7 H7AC 109.5 . . ?
H7AB C7 H7AC 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8AB 109.5 . . ?
H8A C8 H8AB 109.5 . . ?
C6 C8 H8AC 109.5 . . ?
H8A C8 H8AC 109.5 . . ?
H8AB C8 H8AC 109.5 . . ?
O1Bb N9 C10 126.5(11) . . ?
O1Bb N9 C6 117.1(11) . . ?
C10 N9 C6 107.8(5) . . ?
N9 C10 N2 113.7(5) . . ?
N9 C10 C11 124.3(5) . . ?
N2 C10 C11 122.0(5) . . ?
C15 C11 C12 107.3(5) . . ?
C15 C11 C10 123.9(5) . . ?
C12 C11 C10 128.8(5) . . ?
C15 C11 RE 72.1(3) . . ?
C12 C11 RE 72.2(3) . . ?
C10 C11 RE 122.2(4) . . ?
C13 C12 C11 107.8(5) . . ?
C13 C12 RE 71.8(3) . . ?
C11 C12 RE 71.5(3) . . ?
C13 C12 H12 126.0 . . ?
C11 C12 H12 126.0 . . ?
RE C12 H12 126.0 . . ?
C14 C13 C12 108.3(5) . . ?
C14 C13 RE 72.7(3) . . ?
C12 C13 RE 72.2(3) . . ?
C14 C13 H13 125.7 . . ?
C12 C13 H13 125.7 . . ?
RE C13 H13 125.7 . . ?
C15 C14 C13 108.0(5) . . ?
C15 C14 RE 71.6(3) . . ?
C13 C14 RE 71.5(3) . . ?
C15 C14 H14 125.9 . . ?
C13 C14 H14 125.9 . . ?
RE C14 H14 125.9 . . ?
C14 C15 C11 108.7(5) . . ?
C14 C15 RE 72.8(3) . . ?
C11 C15 RE 71.8(3) . . ?
C14 C15 H15 125.6 . . ?
C11 C15 H15 125.6 . . ?
RE C15 H15 125.6 . . ?
O2C C1C RE 176.8(7) . . ?
O4C C3C RE 176.9(7) . . ?
O6C C5C RE 177.4(6) . . ?

_refine_diff_density_max         1.147
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.149

