# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
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data_m23279
_database_code_depnum_ccdc_archive 'CCDC 2428908'
loop_
_audit_author_name
_audit_author_address
'Sean Parkin'
;University of Kentucky
United States of America
;
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2022). 
# CIFFIX: https://xray.uky.edu/Resources/scripts/ciffix 
_audit_update_record             
;
2025-03-05 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-2019/2 and CIFFIX'

_shelx_SHELXL_version_number     2019/2

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 Br2 N3 O3 Re'
_chemical_formula_sum            'C21 H18 Br2 N3 O3 Re'
_chemical_formula_weight         706.40

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'
Br Br -0.2901 2.4595 '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                   11.7322(3)
_cell_length_b                   11.2485(2)
_cell_length_c                   17.8809(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.108(1)
_cell_angle_gamma                90
_cell_volume                     2288.56(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9210
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.50

_exptl_crystal_description       'cut block'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.050
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    8.828
_shelx_estimated_absorpt_T_min   0.371
_shelx_estimated_absorpt_T_max   0.443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.378
_exptl_absorpt_correction_T_max  0.505
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by X-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the X-ray beam cross section, absorption by the crystal 
mount, scan truncation etc. These account, by and large, for the difference 
between SHELX estimates of Tmin and Tmax and the _exptl_absorpt_correction_ 
values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 100K. 
;

_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            46047
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999

_reflns_number_total             5254
_reflns_number_gt                4860
_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       'APEX3 (Bruker-AXS, 2016)'
_computing_cell_refinement       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'APEX3 (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2020) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0084P)²+2.2784P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.00052(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5254
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0179
_refine_ls_R_factor_gt           0.0149
_refine_ls_wR_factor_ref         0.0299
_refine_ls_wR_factor_gt          0.0292
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
Re1 Re 0.73221(2) 0.61369(2) 0.36582(2) 0.01302(3) Uani 1 1 d . . . . .
Br1 Br 0.52431(2) 0.71398(2) 0.32615(2) 0.01815(5) Uani 1 1 d . . . . .
Br2 Br 0.88794(2) 1.25484(2) 0.48180(2) 0.02481(6) Uani 1 1 d . . . . .
O1 O 0.85017(14) 0.83491(14) 0.31864(9) 0.0215(3) Uani 1 1 d . . . . .
O2 O 0.70829(17) 0.53149(17) 0.19930(9) 0.0346(4) Uani 1 1 d . . . . .
O3 O 0.97510(14) 0.49765(14) 0.41184(9) 0.0221(3) Uani 1 1 d . . . . .
N1 N 0.64348(15) 0.46122(15) 0.40283(9) 0.0132(3) Uani 1 1 d . . . . .
N2 N 0.72840(15) 0.65039(15) 0.48525(9) 0.0127(3) Uani 1 1 d . . . . .
N3 N 0.72348(15) 0.57845(16) 0.59950(9) 0.0136(4) Uani 1 1 d . . . . .
C1 C 0.80602(19) 0.7527(2) 0.33863(11) 0.0168(4) Uani 1 1 d . . . . .
C2 C 0.7181(2) 0.5615(2) 0.26221(13) 0.0215(5) Uani 1 1 d . . . . .
C3 C 0.8838(2) 0.54022(18) 0.39587(11) 0.0157(4) Uani 1 1 d . . . . .
C4 C 0.58962(19) 0.37430(19) 0.35545(12) 0.0166(4) Uani 1 1 d . . . . .
H4 H 0.588157 0.379506 0.302192 0.020 Uiso 1 1 calc R U . . .
C5 C 0.53653(19) 0.27814(19) 0.38065(12) 0.0175(4) Uani 1 1 d . . . . .
H5 H 0.499017 0.218746 0.345377 0.021 Uiso 1 1 calc R U . . .
C6 C 0.53874(19) 0.26951(19) 0.45809(12) 0.0178(4) Uani 1 1 d . . . . .
H6 H 0.503178 0.203738 0.476871 0.021 Uiso 1 1 calc R U . . .
C7 C 0.59325(18) 0.35765(18) 0.50781(12) 0.0154(4) Uani 1 1 d . . . . .
H7 H 0.595253 0.353355 0.561173 0.018 Uiso 1 1 calc R U . . .
C8 C 0.64533(18) 0.45299(18) 0.47902(11) 0.0129(4) Uani 1 1 d . . . . .
C9 C 0.69978(18) 0.55617(18) 0.52274(11) 0.0124(4) Uani 1 1 d . . . . .
C10 C 0.76690(18) 0.69162(19) 0.61027(12) 0.0151(4) Uani 1 1 d . . . . .
H10 H 0.791437 0.731526 0.658340 0.018 Uiso 1 1 calc R U . . .
C11 C 0.76882(18) 0.73743(19) 0.53949(11) 0.0141(4) Uani 1 1 d . . . . .
C12 C 0.79875(18) 0.85963(19) 0.52299(12) 0.0150(4) Uani 1 1 d . . . . .
C13 C 0.73326(19) 0.9211(2) 0.45934(13) 0.0182(4) Uani 1 1 d . . . . .
H13 H 0.670549 0.882279 0.424145 0.022 Uiso 1 1 calc R U . . .
C14 C 0.75905(19) 1.03877(19) 0.44702(13) 0.0189(5) Uani 1 1 d . . . . .
H14 H 0.715040 1.080371 0.403185 0.023 Uiso 1 1 calc R U . . .
C15 C 0.8492(2) 1.09471(19) 0.49906(13) 0.0185(5) Uani 1 1 d . . . . .
C16 C 0.91468(19) 1.0358(2) 0.56297(13) 0.0198(5) Uani 1 1 d . . . . .
H16 H 0.976398 1.075576 0.598426 0.024 Uiso 1 1 calc R U . . .
C17 C 0.88926(19) 0.91814(19) 0.57476(12) 0.0168(4) Uani 1 1 d . . . . .
H17 H 0.933953 0.876955 0.618542 0.020 Uiso 1 1 calc R U . . .
C18 C 0.71719(19) 0.49948(19) 0.66431(11) 0.0160(4) Uani 1 1 d . . . . .
H18A H 0.639164 0.460599 0.653320 0.019 Uiso 1 1 calc R U . . .
H18B H 0.725914 0.547450 0.711794 0.019 Uiso 1 1 calc R U . . .
C19 C 0.8126(2) 0.4047(2) 0.67749(12) 0.0212(5) Uani 1 1 d . . . . .
H19A H 0.889737 0.443465 0.682106 0.025 Uiso 1 1 calc R U . . .
H19B H 0.798200 0.351169 0.632193 0.025 Uiso 1 1 calc R U . . .
C20 C 0.8171(2) 0.3311(2) 0.74968(13) 0.0230(5) Uani 1 1 d . . . . .
H20A H 0.839896 0.382976 0.795634 0.028 Uiso 1 1 calc R U . . .
H20B H 0.737841 0.298890 0.747650 0.028 Uiso 1 1 calc R U . . .
C21 C 0.9038(2) 0.2292(2) 0.75744(14) 0.0333(6) Uani 1 1 d . . . . .
H21A H 0.876593 0.172766 0.715072 0.050 Uiso 1 1 calc R U . . .
H21B H 0.909880 0.188660 0.806776 0.050 Uiso 1 1 calc R U . . .
H21C H 0.981109 0.260205 0.755479 0.050 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 C1 1.907(2) . ?
Re1 C2 1.912(2) . ?
Re1 C3 1.915(2) . ?
Re1 N2 2.1863(16) . ?
Re1 N1 2.1907(17) . ?
Re1 Br1 2.6233(2) . ?
Br2 C15 1.901(2) . ?
O1 C1 1.158(3) . ?
O2 C2 1.153(3) . ?
O3 C3 1.144(3) . ?
N1 C4 1.346(3) . ?
N1 C8 1.360(2) . ?
N2 C9 1.340(3) . ?
N2 C11 1.378(3) . ?
N3 C9 1.356(2) . ?
N3 C10 1.367(3) . ?
N3 C18 1.476(2) . ?
C4 C5 1.378(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.457(3) . ?
C10 C11 1.372(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.466(3) . ?
C12 C13 1.392(3) . ?
C12 C17 1.392(3) . ?
C13 C14 1.387(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(3) . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.522(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.523(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.517(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C1 Re1 C2 86.69(9) . . ?
C1 Re1 C3 88.69(9) . . ?
C2 Re1 C3 89.68(9) . . ?
C1 Re1 N2 102.29(8) . . ?
C2 Re1 N2 170.77(8) . . ?
C3 Re1 N2 92.64(7) . . ?
C1 Re1 N1 176.14(8) . . ?
C2 Re1 N1 96.72(8) . . ?
C3 Re1 N1 93.12(7) . . ?
N2 Re1 N1 74.24(6) . . ?
C1 Re1 Br1 91.63(6) . . ?
C2 Re1 Br1 90.86(7) . . ?
C3 Re1 Br1 179.38(6) . . ?
N2 Re1 Br1 86.78(5) . . ?
N1 Re1 Br1 86.53(5) . . ?
C4 N1 C8 118.12(17) . . ?
C4 N1 Re1 124.28(13) . . ?
C8 N1 Re1 117.59(13) . . ?
C9 N2 C11 107.17(16) . . ?
C9 N2 Re1 113.99(13) . . ?
C11 N2 Re1 137.39(14) . . ?
C9 N3 C10 106.99(17) . . ?
C9 N3 C18 130.27(18) . . ?
C10 N3 C18 122.54(17) . . ?
O1 C1 Re1 176.74(18) . . ?
O2 C2 Re1 178.9(2) . . ?
O3 C3 Re1 177.92(18) . . ?
N1 C4 C5 123.00(19) . . ?
N1 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 119.2(2) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 119.40(19) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
N1 C8 C7 121.40(18) . . ?
N1 C8 C9 112.40(17) . . ?
C7 C8 C9 126.10(18) . . ?
N2 C9 N3 110.23(18) . . ?
N2 C9 C8 119.49(17) . . ?
N3 C9 C8 130.19(18) . . ?
N3 C10 C11 108.01(18) . . ?
N3 C10 H10 126.0 . . ?
C11 C10 H10 126.0 . . ?
C10 C11 N2 107.58(18) . . ?
C10 C11 C12 126.60(19) . . ?
N2 C11 C12 125.63(18) . . ?
C13 C12 C17 119.2(2) . . ?
C13 C12 C11 121.24(19) . . ?
C17 C12 C11 119.39(19) . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 121.3(2) . . ?
C14 C15 Br2 119.81(17) . . ?
C16 C15 Br2 118.84(17) . . ?
C15 C16 C17 119.2(2) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C12 120.6(2) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
N3 C18 C19 111.57(16) . . ?
N3 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
N3 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 C20 112.58(18) . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 111.83(19) . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C8 N1 C4 C5 0.1(3) . . . . ?
Re1 N1 C4 C5 178.65(16) . . . . ?
N1 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C4 N1 C8 C7 0.0(3) . . . . ?
Re1 N1 C8 C7 -178.63(15) . . . . ?
C4 N1 C8 C9 -176.44(18) . . . . ?
Re1 N1 C8 C9 4.9(2) . . . . ?
C6 C7 C8 N1 0.1(3) . . . . ?
C6 C7 C8 C9 176.1(2) . . . . ?
C11 N2 C9 N3 -1.7(2) . . . . ?
Re1 N2 C9 N3 167.01(13) . . . . ?
C11 N2 C9 C8 175.20(18) . . . . ?
Re1 N2 C9 C8 -16.1(2) . . . . ?
C10 N3 C9 N2 0.9(2) . . . . ?
C18 N3 C9 N2 -173.87(19) . . . . ?
C10 N3 C9 C8 -175.5(2) . . . . ?
C18 N3 C9 C8 9.7(4) . . . . ?
N1 C8 C9 N2 7.6(3) . . . . ?
C7 C8 C9 N2 -168.6(2) . . . . ?
N1 C8 C9 N3 -176.2(2) . . . . ?
C7 C8 C9 N3 7.5(4) . . . . ?
C9 N3 C10 C11 0.2(2) . . . . ?
C18 N3 C10 C11 175.50(18) . . . . ?
N3 C10 C11 N2 -1.2(2) . . . . ?
N3 C10 C11 C12 174.1(2) . . . . ?
C9 N2 C11 C10 1.8(2) . . . . ?
Re1 N2 C11 C10 -162.90(16) . . . . ?
C9 N2 C11 C12 -173.6(2) . . . . ?
Re1 N2 C11 C12 21.7(3) . . . . ?
C10 C11 C12 C13 -137.0(2) . . . . ?
N2 C11 C12 C13 37.5(3) . . . . ?
C10 C11 C12 C17 38.6(3) . . . . ?
N2 C11 C12 C17 -146.9(2) . . . . ?
C17 C12 C13 C14 1.0(3) . . . . ?
C11 C12 C13 C14 176.52(19) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C13 C14 C15 Br2 178.62(16) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
Br2 C15 C16 C17 -178.15(16) . . . . ?
C15 C16 C17 C12 -0.1(3) . . . . ?
C13 C12 C17 C16 -0.5(3) . . . . ?
C11 C12 C17 C16 -176.11(19) . . . . ?
C9 N3 C18 C19 69.5(3) . . . . ?
C10 N3 C18 C19 -104.6(2) . . . . ?
N3 C18 C19 C20 173.35(18) . . . . ?
C18 C19 C20 C21 174.1(2) . . . . ?

_refine_diff_density_max         0.709
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_m23269
_database_code_depnum_ccdc_archive 'CCDC 2428909'
loop_
_audit_author_name
_audit_author_address
'Sean Parkin'
;University of Kentucky
United States of America
;
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2022). 
# CIFFIX: https://xray.uky.edu/Resources/scripts/ciffix 
_audit_update_record             
;
2025-03-05 deposited with the CCDC.	2025-04-07 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-2019/2 and CIFFIX'

_shelx_SHELXL_version_number     2019/2

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 Br N3 O3 Re'
_chemical_formula_sum            'C21 H19 Br N3 O3 Re'
_chemical_formula_weight         627.50

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'
Br Br -0.2901 2.4595 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.4135(6)
_cell_length_b                   13.9657(5)
_cell_length_c                   19.9434(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4014.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9766
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      27.51

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.076
_exptl_crystal_F_000             2400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    8.073
_shelx_estimated_absorpt_T_min   0.282
_shelx_estimated_absorpt_T_max   0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.476
_exptl_absorpt_correction_T_max  0.801
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by X-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, 
crystal longer than the X-ray beam cross section, absorption by the crystal 
mount, scan truncation etc. These account, by and large, for the difference 
between SHELX estimates of Tmin and Tmax and the _exptl_absorpt_correction_ 
values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 100K. 
;

_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            43216
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.042
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997

_reflns_number_total             4593
_reflns_number_gt                4349
_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       'APEX3 (Bruker-AXS, 2016)'
_computing_cell_refinement       'APEX3 (Bruker-AXS, 2016)'
_computing_data_reduction        'APEX3 (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2020) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+6.8148P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.00056(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4593
_refine_ls_number_parameters     280
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0195
_refine_ls_wR_factor_ref         0.0440
_refine_ls_wR_factor_gt          0.0434
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.169
_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 0.56275(2) 0.28153(2) 0.34296(2) 0.01142(5) Uani 1 1 d D . . . .
C3 C 0.6887(3) 0.2635(3) 0.3121(2) 0.0134(9) Uani 0.9244(16) 1 d D . P A 1
O3 O 0.7636(3) 0.2511(2) 0.29396(17) 0.0257(8) Uani 0.9244(16) 1 d D . P A 1
Br1 Br 0.39603(2) 0.30402(2) 0.39125(2) 0.01431(11) Uani 0.9244(16) 1 d D . P A
1
C3' C 0.4354(14) 0.293(3) 0.376(2) 0.01431(11) Uani 0.0756(16) 1 d D . P A 2
O3' O 0.3593(14) 0.302(2) 0.3936(16) 0.01431(11) Uani 0.0756(16) 1 d D . P A 2
Br1' Br 0.7297(5) 0.2664(5) 0.3142(4) 0.0246(18) Uani 0.0756(16) 1 d D . P A 2
C1 C 0.53160(19) 0.15035(19) 0.32395(13) 0.0142(5) Uani 1 1 d . . . . .
O1 O 0.50893(14) 0.07354(14) 0.31137(10) 0.0205(4) Uani 1 1 d . . . . .
C2 C 0.5242(2) 0.31014(19) 0.25302(14) 0.0174(5) Uani 1 1 d . . . . .
O2 O 0.50306(16) 0.32746(15) 0.19875(10) 0.0268(5) Uani 1 1 d . . . . .
N1 N 0.58286(15) 0.42988(15) 0.37382(11) 0.0121(4) Uani 1 1 d . . . . .
N2 N 0.60690(15) 0.27438(14) 0.44743(11) 0.0113(4) Uani 1 1 d . . . . .
N3 N 0.63749(15) 0.34786(15) 0.54345(10) 0.0123(4) Uani 1 1 d . . . . .
C4 C 0.57285(18) 0.50473(19) 0.33232(14) 0.0143(5) Uani 1 1 d . . . . .
H4 H 0.561714 0.492498 0.286153 0.017 Uiso 1 1 calc R U . . .
C5 C 0.57799(19) 0.59918(19) 0.35359(14) 0.0168(6) Uani 1 1 d . . . . .
H5 H 0.572623 0.650451 0.322528 0.020 Uiso 1 1 calc R U . . .
C6 C 0.59111(19) 0.61673(19) 0.42109(14) 0.0173(5) Uani 1 1 d . . . . .
H6 H 0.592317 0.680586 0.437490 0.021 Uiso 1 1 calc R U . . .
C7 C 0.60248(19) 0.54047(18) 0.46457(14) 0.0156(5) Uani 1 1 d . . . . .
H7 H 0.612538 0.551617 0.510998 0.019 Uiso 1 1 calc R U . . .
C8 C 0.59911(18) 0.44732(18) 0.43992(13) 0.0118(5) Uani 1 1 d . . . . .
C9 C 0.61367(17) 0.35966(18) 0.47802(13) 0.0117(5) Uani 1 1 d . . . . .
C10 C 0.64618(19) 0.25164(19) 0.55415(13) 0.0148(5) Uani 1 1 d . . . . .
H10 H 0.662245 0.221798 0.595354 0.018 Uiso 1 1 calc R U . . .
C11 C 0.62759(18) 0.20581(18) 0.49483(13) 0.0128(5) Uani 1 1 d . . . . .
C12 C 0.63234(18) 0.10166(18) 0.48342(14) 0.0146(5) Uani 1 1 d . . . . .
C13 C 0.66866(19) 0.06318(19) 0.42443(14) 0.0180(6) Uani 1 1 d . . . . .
H13 H 0.689438 0.104599 0.389757 0.022 Uiso 1 1 calc R U . . .
C14 C 0.6746(2) -0.0353(2) 0.41616(16) 0.0227(6) Uani 1 1 d . . . . .
H14 H 0.697141 -0.061061 0.375199 0.027 Uiso 1 1 calc R U . . .
C15 C 0.6477(2) -0.0961(2) 0.46750(17) 0.0252(7) Uani 1 1 d . . . . .
H15 H 0.653196 -0.163434 0.462111 0.030 Uiso 1 1 calc R U . . .
C16 C 0.6129(2) -0.0588(2) 0.52653(16) 0.0239(6) Uani 1 1 d . . . . .
H16 H 0.595193 -0.100606 0.561854 0.029 Uiso 1 1 calc R U . . .
C17 C 0.6037(2) 0.0394(2) 0.53444(15) 0.0187(6) Uani 1 1 d . . . . .
H17 H 0.577947 0.064509 0.574596 0.022 Uiso 1 1 calc R U . . .
C18 C 0.65685(19) 0.42394(18) 0.59324(12) 0.0139(5) Uani 1 1 d . . . . .
H18A H 0.601373 0.465249 0.597687 0.017 Uiso 1 1 calc R U . . .
H18B H 0.708496 0.464247 0.576687 0.017 Uiso 1 1 calc R U . . .
C19 C 0.6822(2) 0.38429(19) 0.66177(13) 0.0171(5) Uani 1 1 d . . . . .
H19A H 0.739476 0.345468 0.658181 0.021 Uiso 1 1 calc R U . . .
H19B H 0.631766 0.342208 0.678085 0.021 Uiso 1 1 calc R U . . .
C20 C 0.6976(2) 0.4662(2) 0.71178(14) 0.0191(6) Uani 1 1 d . . . . .
H20A H 0.640310 0.505187 0.714356 0.023 Uiso 1 1 calc R U . . .
H20B H 0.708914 0.438680 0.756782 0.023 Uiso 1 1 calc R U . . .
C21 C 0.7784(2) 0.5312(2) 0.69348(15) 0.0206(6) Uani 1 1 d . . . . .
H21A H 0.833350 0.492143 0.684078 0.031 Uiso 1 1 calc R U . . .
H21B H 0.791497 0.574525 0.730940 0.031 Uiso 1 1 calc R U . . .
H21C H 0.762327 0.568734 0.653621 0.031 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 C2 1.920(3) . ?
Re1 C1 1.924(3) . ?
Re1 C3 1.933(5) . ?
Re1 C3' 1.960(16) . ?
Re1 N1 2.181(2) . ?
Re1 N2 2.181(2) . ?
Re1 Br1' 2.482(8) . ?
Re1 Br1 2.6079(4) . ?
C3 O3 1.151(6) . ?
C3' O3' 1.155(18) . ?
C1 O1 1.149(3) . ?
C2 O2 1.150(3) . ?
N1 C4 1.341(3) . ?
N1 C8 1.361(3) . ?
N2 C9 1.342(3) . ?
N2 C11 1.378(3) . ?
N3 C9 1.360(3) . ?
N3 C10 1.366(3) . ?
N3 C18 1.481(3) . ?
C4 C5 1.388(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.456(3) . ?
C10 C11 1.372(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.474(3) . ?
C12 C13 1.395(4) . ?
C12 C17 1.401(4) . ?
C13 C14 1.388(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.519(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.534(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.520(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C2 Re1 C1 86.94(11) . . ?
C2 Re1 C3 90.05(16) . . ?
C1 Re1 C3 91.87(16) . . ?
C2 Re1 C3' 91.7(12) . . ?
C1 Re1 C3' 85.8(11) . . ?
C2 Re1 N1 95.99(10) . . ?
C1 Re1 N1 172.44(10) . . ?
C3 Re1 N1 95.09(15) . . ?
C3' Re1 N1 87.1(11) . . ?
C2 Re1 N2 170.61(9) . . ?
C1 Re1 N2 102.28(10) . . ?
C3 Re1 N2 91.40(15) . . ?
C3' Re1 N2 87.2(12) . . ?
N1 Re1 N2 74.64(8) . . ?
C2 Re1 Br1' 94.7(2) . . ?
C1 Re1 Br1' 95.71(19) . . ?
C3' Re1 Br1' 173.4(12) . . ?
N1 Re1 Br1' 91.00(18) . . ?
N2 Re1 Br1' 86.2(2) . . ?
C2 Re1 Br1 93.06(9) . . ?
C1 Re1 Br1 88.42(8) . . ?
C3 Re1 Br1 176.88(14) . . ?
N1 Re1 Br1 84.48(6) . . ?
N2 Re1 Br1 85.50(6) . . ?
O3 C3 Re1 178.7(4) . . ?
O3' C3' Re1 177(4) . . ?
O1 C1 Re1 176.7(2) . . ?
O2 C2 Re1 178.6(3) . . ?
C4 N1 C8 118.5(2) . . ?
C4 N1 Re1 123.50(18) . . ?
C8 N1 Re1 117.79(16) . . ?
C9 N2 C11 106.8(2) . . ?
C9 N2 Re1 114.51(16) . . ?
C11 N2 Re1 138.60(17) . . ?
C9 N3 C10 107.0(2) . . ?
C9 N3 C18 127.2(2) . . ?
C10 N3 C18 125.7(2) . . ?
N1 C4 C5 123.1(3) . . ?
N1 C4 H4 118.4 . . ?
C5 C4 H4 118.4 . . ?
C6 C5 C4 118.3(2) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C7 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C8 119.6(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
N1 C8 C7 121.0(2) . . ?
N1 C8 C9 112.3(2) . . ?
C7 C8 C9 126.6(2) . . ?
N2 C9 N3 110.3(2) . . ?
N2 C9 C8 119.9(2) . . ?
N3 C9 C8 129.7(2) . . ?
N3 C10 C11 107.8(2) . . ?
N3 C10 H10 126.1 . . ?
C11 C10 H10 126.1 . . ?
C10 C11 N2 108.0(2) . . ?
C10 C11 C12 125.8(2) . . ?
N2 C11 C12 126.2(2) . . ?
C13 C12 C17 118.9(2) . . ?
C13 C12 C11 121.9(2) . . ?
C17 C12 C11 119.1(2) . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
N3 C18 C19 112.8(2) . . ?
N3 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
N3 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C18 C19 C20 110.4(2) . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C21 C20 C19 113.5(2) . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C8 N1 C4 C5 -0.2(4) . . . . ?
Re1 N1 C4 C5 174.3(2) . . . . ?
N1 C4 C5 C6 -2.1(4) . . . . ?
C4 C5 C6 C7 2.7(4) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C4 N1 C8 C7 2.0(4) . . . . ?
Re1 N1 C8 C7 -172.9(2) . . . . ?
C4 N1 C8 C9 -176.7(2) . . . . ?
Re1 N1 C8 C9 8.4(3) . . . . ?
C6 C7 C8 N1 -1.4(4) . . . . ?
C6 C7 C8 C9 177.1(3) . . . . ?
C11 N2 C9 N3 -0.3(3) . . . . ?
Re1 N2 C9 N3 177.31(16) . . . . ?
C11 N2 C9 C8 177.6(2) . . . . ?
Re1 N2 C9 C8 -4.7(3) . . . . ?
C10 N3 C9 N2 0.2(3) . . . . ?
C18 N3 C9 N2 176.4(2) . . . . ?
C10 N3 C9 C8 -177.6(3) . . . . ?
C18 N3 C9 C8 -1.3(4) . . . . ?
N1 C8 C9 N2 -2.3(3) . . . . ?
C7 C8 C9 N2 179.1(3) . . . . ?
N1 C8 C9 N3 175.2(2) . . . . ?
C7 C8 C9 N3 -3.4(5) . . . . ?
C9 N3 C10 C11 0.1(3) . . . . ?
C18 N3 C10 C11 -176.2(2) . . . . ?
N3 C10 C11 N2 -0.3(3) . . . . ?
N3 C10 C11 C12 177.7(2) . . . . ?
C9 N2 C11 C10 0.4(3) . . . . ?
Re1 N2 C11 C10 -176.4(2) . . . . ?
C9 N2 C11 C12 -177.6(3) . . . . ?
Re1 N2 C11 C12 5.7(4) . . . . ?
C10 C11 C12 C13 -139.6(3) . . . . ?
N2 C11 C12 C13 38.0(4) . . . . ?
C10 C11 C12 C17 37.2(4) . . . . ?
N2 C11 C12 C17 -145.1(3) . . . . ?
C17 C12 C13 C14 1.2(4) . . . . ?
C11 C12 C13 C14 178.1(2) . . . . ?
C12 C13 C14 C15 -2.4(4) . . . . ?
C13 C14 C15 C16 1.5(4) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C15 C16 C17 C12 -2.0(4) . . . . ?
C13 C12 C17 C16 1.0(4) . . . . ?
C11 C12 C17 C16 -176.0(3) . . . . ?
C9 N3 C18 C19 -179.5(2) . . . . ?
C10 N3 C18 C19 -4.0(4) . . . . ?
N3 C18 C19 C20 -177.7(2) . . . . ?
C18 C19 C20 C21 -63.2(3) . . . . ?

_refine_diff_density_max         0.652
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.101

