# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_pnnm
_database_code_depnum_ccdc_archive 'CCDC 2243049'
loop_
_audit_author_name
_audit_author_address
'Peter Junk'
;James Cook University
Australia
;
_audit_update_record             
;
2023-02-19 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_audit_creation_date             2023-02-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C50 H70 Bi2 N4'
_chemical_formula_sum            'C50 H70 Bi2 N4'
_chemical_formula_weight         1145.06
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           58
_space_group_name_H-M_alt        'P n n m'
_space_group_name_Hall           '-P 2 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, y, -z'
'-x-1/2, y-1/2, z-1/2'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.348(4)
_cell_length_b                   19.217(4)
_cell_length_c                   10.939(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3857.0(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3524
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.2
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.579
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.986
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            45171
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         2.220
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3238
_reflns_number_total             3524
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         4.389
_refine_diff_density_min         -6.662
_refine_diff_density_rms         0.258
_refine_ls_extinction_coef       0.0162(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     111
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0839
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+112.6086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2071
_refine_ls_wR_factor_ref         0.2102
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 Bi1, N1, C8, C1, N2, C2, C9, C3, C5, C10, C4, C7, C6, C11, C14, C12, C13, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C5(H5), C14(H14)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C8(H8), C11(H11), C12(H12)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.56801(3) 0.96582(3) 1.000000 0.0390(4) Uani 1 2 d S T P . .
N2 N 0.3845(7) 0.9177(8) 1.000000 0.036(3) Uani 1 2 d S T P . .
N1 N 0.4963(8) 0.8636(8) 1.000000 0.044(4) Uani 1 2 d S T P . .
C4 C 0.6030(14) 0.6747(16) 1.000000 0.131(10) Uani 1 2 d S T P . .
H4 H 0.630210 0.632659 0.999999 0.157 Uiso 1 2 calc R U P . .
C9 C 0.3058(8) 0.9091(8) 1.000000 0.024(3) Uani 1 2 d S T P . .
C3 C 0.5847(10) 0.7030(10) 0.880(4) 0.124(9) Uani 1 1 d . . . . .
H3 H 0.596033 0.679673 0.806036 0.149 Uiso 1 1 calc R U . . .
C10 C 0.2686(6) 0.9050(6) 0.8923(11) 0.033(2) Uani 1 1 d . . . . .
C5 C 0.5311(10) 0.7990(10) 0.761(2) 0.090(5) Uani 1 1 d . . . . .
H5 H 0.499286 0.840362 0.777033 0.108 Uiso 1 1 calc R U . . .
C8 C 0.4231(9) 0.8628(11) 1.000000 0.042(4) Uani 1 2 d S T P . .
H8 H 0.399036 0.819018 1.000000 0.050 Uiso 1 2 calc R U P . .
C11 C 0.1917(6) 0.8961(7) 0.8919(14) 0.048(3) Uani 1 1 d . . . . .
H11 H 0.165547 0.892776 0.817122 0.057 Uiso 1 1 calc R U . . .
C12 C 0.1568(9) 0.8925(9) 1.000000 0.045(4) Uani 1 2 d S T P . .
H12 H 0.105331 0.887214 0.999999 0.053 Uiso 1 2 calc R U P . .
C2 C 0.5495(8) 0.7666(8) 0.884(3) 0.084(4) Uani 1 1 d . . . . .
C14 C 0.3074(8) 0.9111(9) 0.7659(13) 0.059(4) Uani 1 1 d . . . . .
H14 H 0.358682 0.925475 0.783896 0.071 Uiso 1 1 calc R U . . .
C1 C 0.5321(11) 0.7973(11) 1.000000 0.070(5) Uani 1 2 d S T P . .
C7 C 0.6016(12) 0.8247(16) 0.710(3) 0.134(10) Uani 1 1 d . . . . .
H7A H 0.633791 0.839130 0.776599 0.201 Uiso 1 1 calc R U . . .
H7B H 0.592229 0.864521 0.655963 0.201 Uiso 1 1 calc R U . . .
H7C H 0.624883 0.787402 0.662926 0.201 Uiso 1 1 calc R U . . .
C13 C 0.2744(12) 0.9701(13) 0.6817(16) 0.106(8) Uani 1 1 d . . . . .
H13A H 0.232419 0.951674 0.636796 0.160 Uiso 1 1 calc R U . . .
H13B H 0.311545 0.985893 0.623584 0.160 Uiso 1 1 calc R U . . .
H13C H 0.258805 1.009368 0.732562 0.160 Uiso 1 1 calc R U . . .
C15 C 0.3130(12) 0.8392(13) 0.696(2) 0.104(7) Uani 1 1 d . . . . .
H15A H 0.314381 0.801029 0.755233 0.155 Uiso 1 1 calc R U . . .
H15B H 0.357601 0.838456 0.646493 0.155 Uiso 1 1 calc R U . . .
H15C H 0.270564 0.833567 0.642389 0.155 Uiso 1 1 calc R U . . .
C6 C 0.4890(11) 0.7490(13) 0.681(3) 0.125(9) Uani 1 1 d . . . . .
H6A H 0.523292 0.718941 0.636929 0.188 Uiso 1 1 calc R U . . .
H6B H 0.459704 0.775315 0.622130 0.188 Uiso 1 1 calc R U . . .
H6C H 0.456943 0.720300 0.731860 0.188 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
Bi1 Bi1 2.8204(14) 5_677 ?
Bi1 N2 2.402(15) 5_677 ?
Bi1 N1 2.365(15) . ?
N2 C9 1.454(19) . ?
N2 C8 1.27(2) . ?
N1 C8 1.34(2) . ?
N1 C1 1.43(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.46(4) 6_557 ?
C4 C3 1.46(4) . ?
C9 C10 1.363(13) 6_557 ?
C9 C10 1.363(13) . ?
C3 H3 0.9500 . ?
C3 C2 1.38(2) . ?
C10 C11 1.421(16) . ?
C10 C14 1.560(18) . ?
C5 H5 1.0000 . ?
C5 C2 1.51(3) . ?
C5 C7 1.50(3) . ?
C5 C6 1.51(3) . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.347(17) . ?
C12 H12 0.9500 . ?
C2 C1 1.44(2) . ?
C14 H14 1.0000 . ?
C14 C13 1.58(2) . ?
C14 C15 1.58(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Bi1 Bi1 83.5(3) 5_677 5_677 ?
N1 Bi1 Bi1 83.9(3) . 5_677 ?
N1 Bi1 N2 167.4(5) . 5_677 ?
C9 N2 Bi1 117.8(10) . 5_677 ?
C8 N2 Bi1 124.9(12) . 5_677 ?
C8 N2 C9 117.4(15) . . ?
C8 N1 Bi1 124.5(13) . . ?
C8 N1 C1 116.7(17) . . ?
C1 N1 Bi1 118.8(12) . . ?
C3 C4 H4 116.0 6_557 . ?
C3 C4 H4 116.0 . . ?
C3 C4 C3 128(3) . 6_557 ?
C10 C9 N2 120.3(7) 6_557 . ?
C10 C9 N2 120.3(7) . . ?
C10 C9 C10 119.5(14) 6_557 . ?
C4 C3 H3 122.8 . . ?
C2 C3 C4 114(3) . . ?
C2 C3 H3 122.8 . . ?
C9 C10 C11 120.5(12) . . ?
C9 C10 C14 122.2(10) . . ?
C11 C10 C14 117.3(11) . . ?
C2 C5 H5 107.9 . . ?
C7 C5 H5 107.9 . . ?
C7 C5 C2 106(2) . . ?
C7 C5 C6 116(2) . . ?
C6 C5 H5 107.9 . . ?
C6 C5 C2 111(2) . . ?
N2 C8 N1 123.2(19) . . ?
N2 C8 H8 118.4 . . ?
N1 C8 H8 118.4 . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.3(13) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 C11 122.9(16) 6_557 . ?
C11 C12 H12 118.6 6_557 . ?
C11 C12 H12 118.6 . . ?
C3 C2 C5 116(2) . . ?
C3 C2 C1 119(3) . . ?
C1 C2 C5 124.2(14) . . ?
C10 C14 H14 106.0 . . ?
C10 C14 C13 113.2(12) . . ?
C10 C14 C15 113.2(15) . . ?
C13 C14 H14 106.0 . . ?
C13 C14 C15 111.6(16) . . ?
C15 C14 H14 106.0 . . ?
N1 C1 C2 117.8(11) . . ?
N1 C1 C2 117.8(11) . 6_557 ?
C2 C1 C2 124(2) . 6_557 ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
Bi1 N2 C9 C10 -90.0(13) 5_677 . . 6_557 ?
Bi1 N2 C9 C10 90.0(13) 5_677 . . . ?
Bi1 N2 C8 N1 0.0 5_677 . . . ?
Bi1 N1 C8 N2 0.0 . . . . ?
Bi1 N1 C1 C2 89.4(16) . . . 6_557 ?
Bi1 N1 C1 C2 -89.4(16) . . . . ?
N2 C9 C10 C11 179.5(13) . . . . ?
N2 C9 C10 C14 -1(2) . . . . ?
C4 C3 C2 C5 178.5(18) . . . . ?
C4 C3 C2 C1 -2(3) . . . . ?
C9 N2 C8 N1 180.0 . . . . ?
C9 C10 C11 C12 1(2) . . . . ?
C9 C10 C14 C13 -124.8(17) . . . . ?
C9 C10 C14 C15 106.8(17) . . . . ?
C3 C4 C3 C2 4(4) 6_557 . . . ?
C3 C2 C1 N1 179.4(16) . . . . ?
C3 C2 C1 C2 1(3) . . . 6_557 ?
C10 C9 C10 C11 -1(2) 6_557 . . . ?
C10 C9 C10 C14 178.5(11) 6_557 . . . ?
C10 C11 C12 C11 -1(3) . . . 6_557 ?
C5 C2 C1 N1 -1(3) . . . . ?
C5 C2 C1 C2 179.9(14) . . . 6_557 ?
C8 N2 C9 C10 90.0(13) . . . 6_557 ?
C8 N2 C9 C10 -90.0(13) . . . . ?
C8 N1 C1 C2 -90.6(16) . . . 6_557 ?
C8 N1 C1 C2 90.6(16) . . . . ?
C11 C10 C14 C13 54(2) . . . . ?
C11 C10 C14 C15 -74.1(17) . . . . ?
C14 C10 C11 C12 -178.4(14) . . . . ?
C1 N1 C8 N2 180.0 . . . . ?
C7 C5 C2 C3 -73(2) . . . . ?
C7 C5 C2 C1 107(2) . . . . ?
C6 C5 C2 C3 53(2) . . . . ?
C6 C5 C2 C1 -126.3(18) . . . . ?

_platon_squeeze_details          ?
_platon_squeeze_special_details  ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.010 0.000 -0.109 957 255 ' '
2 -0.053 0.500 -0.012 957 255 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT971_pnnm                
;
PROBLEM: Check Calcd Resid. Dens.  1.37Ang From C9              4.97 eA-3  
RESPONSE: The atom type is correct and there is no evidence of twinning.The
large residual density may due to decompose and has no chemical significance.
;
_vrf_PLAT972_pnnm                
;
PROBLEM: Check Calcd Resid. Dens.  1.16Ang From C9             -7.26 eA-3  
RESPONSE: The atom type is correct and there is no evidence of twinning.The
large residual density may due to decompose and has no chemical significance.
;
_vrf_PLAT342_pnnm                
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02564 Ang.  
RESPONSE: The orange crystal of Bi2DippForm2 decomposed within second in MX1,
the diffractions became weaker and weaker during the x-ray measurment, led to
many of the data can not use
;
# end Validation Reply Form

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2243054'
loop_
_audit_author_name
_audit_author_address
'Peter Junk'
;James Cook University
Australia
;
_audit_update_record             
;
2023-02-19 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_audit_creation_date             2023-01-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C60 H44 Bi2 N8, C4 H8 O2'
_chemical_formula_sum            'C64 H52 Bi2 N8 O2'
_chemical_formula_weight         1383.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7300(19)
_cell_length_b                   12.096(2)
_cell_length_c                   12.680(3)
_cell_angle_alpha                117.21(3)
_cell_angle_beta                 90.85(3)
_cell_angle_gamma                101.57(3)
_cell_volume                     1290.5(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    792
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      2
_shelx_estimated_absorpt_T_max   0.610
_shelx_estimated_absorpt_T_min   0.547
_exptl_absorpt_coefficient_mu    6.865
_exptl_absorpt_correction_T_max  0.918
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS(Kabsch, 1993)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             674
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23882
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.820
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4271
_reflns_number_total             4548
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_refine_diff_density_max         2.071
_refine_diff_density_min         -2.011
_refine_diff_density_rms         0.177
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4548
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+3.6203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0909
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H5(0.033) H20(0.033) H8(0.029) H23(0.028) H16(0.036) H4(0.036)
 H26(0.036) H30(0.028) H1(0.034) H2(0.038) H19(0.037) H15(0.043) H27(0.038)
 H17(0.042) H18(0.041) H3(0.042) H28(0.036) H14(0.05) H29(0.035) H13(0.062)
 H13A(0.062) H11(0.075) H11A(0.075) H12(0.062) H31B(0.079) H31A(0.079)
 H31D(0.079) H31C(0.079) H32A(0.134) H32B(0.134) H32C(0.134) H32D(0.134)
 H12A(0.062)
 Fixed X: H5(0.184741) H20(0.91799) H8(0.137185) H23(0.933507) H16(0.508949)
 H4(0.147169) H26(0.719404) H30(1.087904) H1(0.20649) H2(0.181608)
 H19(0.877222) H15(0.091437) H27(0.83652) H17(0.469271) H18(0.655085)
 H3(0.148344) H28(1.076456) H14(0.109881) H29(1.201383) H13(0.300276)
 H13A(0.319155) H11(0.459091) H11A(0.477438) H12(0.511556) H31B(0.658008)
 H31A(0.561047) H31D(0.633721) H31C(0.476014) H32A(0.420735) H32B(0.584193)
 H32C(0.490044) H32D(0.592685) H12A(0.446608)
 Fixed Y: H5(0.496425) H20(0.825626) H8(0.531237) H23(0.772974) H16(0.677603)
 H4(0.476474) H26(0.874084) H30(0.876914) H1(0.876622) H2(0.858423)
 H19(0.733579) H15(0.482489) H27(0.885033) H17(0.587451) H18(0.61076)
 H3(0.656126) H28(0.888132) H14(0.383197) H29(0.883897) H13(0.461514)
 H13A(0.438729) H11(0.735463) H11A(0.712327) H12(0.57841) H31B(0.995186)
 H31A(0.883721) H31D(0.912156) H31C(0.926429) H32A(0.813685) H32B(0.816936)
 H32C(0.777094) H32D(0.888836) H12A(0.658421)
 Fixed Z: H5(0.483753) H20(0.697062) H8(0.303009) H23(0.452436) H16(0.550733)
 H4(0.657993) H26(0.194941) H30(0.350254) H1(0.672188) H2(0.848316)
 H19(0.823148) H15(0.093079) H27(0.039431) H17(0.679042) H18(0.81196)
 H3(0.838642) H28(0.037336) H14(-0.110412) H29(0.192368) H13(-0.184228) H13A(-
 0.179264) H11(0.146784) H11A(0.151063) H12(-0.043857) H31B(0.943447)
 H31A(0.827213) H31D(0.862997) H31C(0.853547) H32A(0.945706) H32B(0.972072)
 H32C(0.923634) H32D(1.040934) H12A(-0.058892)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.47974(2) 0.98417(2) 0.60468(2) 0.01842(10) Uani 1 1 d . . . . .
N2 N 0.3421(5) 0.7928(5) 0.3489(4) 0.0202(10) Uani 1 1 d . . . . .
N1 N 0.3197(5) 0.8105(5) 0.4606(4) 0.0199(10) Uani 1 1 d . . . . .
N3 N 0.6518(5) 0.8696(5) 0.5022(5) 0.0211(10) Uani 1 1 d . . . . .
N4 N 0.6961(5) 0.8991(5) 0.4148(4) 0.0208(10) Uani 1 1 d . . . . .
C9 C 0.2678(6) 0.6726(6) 0.2731(5) 0.0228(13) Uani 1 1 d . . . . .
C21 C 0.7190(7) 0.7593(6) 0.6099(6) 0.0236(13) Uani 1 1 d . . . . .
C22 C 0.7454(6) 0.8125(6) 0.5258(5) 0.0222(12) Uani 1 1 d . . . . .
C5 C 0.1835(7) 0.5697(6) 0.5572(6) 0.0275(14) Uani 1 1 d . . . . .
H5 H 0.184741 0.496425 0.483753 0.033 Uiso 1 1 calc R U . . .
C24 C 0.8182(6) 0.8625(6) 0.3857(6) 0.0220(13) Uani 1 1 d . . . . .
C25 C 0.8911(7) 0.8745(6) 0.2883(5) 0.0222(13) Uani 1 1 d . . . . .
C10 C 0.2766(7) 0.6156(6) 0.1430(6) 0.0280(14) Uani 1 1 d . . . . .
C20 C 0.8266(7) 0.7762(6) 0.6920(6) 0.0277(14) Uani 1 1 d . . . . .
H20 H 0.917990 0.825626 0.697062 0.033 Uiso 1 1 calc R U . . .
C8 C 0.1977(6) 0.6143(6) 0.3354(6) 0.0245(13) Uani 1 1 d . . . . .
H8 H 0.137185 0.531237 0.303009 0.029 Uiso 1 1 calc R U . . .
C7 C 0.2343(6) 0.7025(6) 0.4546(6) 0.0231(13) Uani 1 1 d . . . . .
C23 C 0.8532(7) 0.8071(6) 0.4542(6) 0.0236(13) Uani 1 1 d . . . . .
H23 H 0.933507 0.772974 0.452436 0.028 Uiso 1 1 calc R U . . .
C16 C 0.5845(7) 0.6887(6) 0.6057(6) 0.0300(14) Uani 1 1 d . . . . .
H16 H 0.508949 0.677603 0.550733 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1618(7) 0.5581(6) 0.6613(6) 0.0298(14) Uani 1 1 d . . . . .
H4 H 0.147169 0.476474 0.657993 0.036 Uiso 1 1 calc R U . . .
C26 C 0.8176(7) 0.8766(6) 0.1954(6) 0.0297(15) Uani 1 1 d . . . . .
H26 H 0.719404 0.874084 0.194941 0.036 Uiso 1 1 calc R U . . .
C30 C 1.0359(6) 0.8778(6) 0.2867(6) 0.0232(13) Uani 1 1 d . . . . .
H30 H 1.087904 0.876914 0.350254 0.028 Uiso 1 1 calc R U . . .
C1 C 0.1981(6) 0.7959(6) 0.6699(6) 0.0286(14) Uani 1 1 d . . . . .
H1 H 0.206490 0.876622 0.672188 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2033(6) 0.6896(6) 0.5627(6) 0.0241(13) Uani 1 1 d . . . . .
C2 C 0.1806(7) 0.7850(7) 0.7744(6) 0.0315(15) Uani 1 1 d . . . . .
H2 H 0.181608 0.858423 0.848316 0.038 Uiso 1 1 calc R U . . .
C19 C 0.8023(7) 0.7214(7) 0.7672(6) 0.0310(14) Uani 1 1 d . . . . .
H19 H 0.877222 0.733579 0.823148 0.037 Uiso 1 1 calc R U . . .
C15 C 0.1722(8) 0.5125(7) 0.0640(7) 0.0355(16) Uani 1 1 d . . . . .
H15 H 0.091437 0.482489 0.093079 0.043 Uiso 1 1 calc R U . . .
C27 C 0.8873(8) 0.8826(7) 0.1026(6) 0.0315(15) Uani 1 1 d . . . . .
H27 H 0.836520 0.885033 0.039431 0.038 Uiso 1 1 calc R U . . .
C17 C 0.5610(7) 0.6348(7) 0.6818(7) 0.0353(16) Uani 1 1 d . . . . .
H17 H 0.469271 0.587451 0.679042 0.042 Uiso 1 1 calc R U . . .
C18 C 0.6707(8) 0.6497(7) 0.7616(6) 0.0345(16) Uani 1 1 d . . . . .
H18 H 0.655085 0.610760 0.811960 0.041 Uiso 1 1 calc R U . . .
C3 C 0.1616(7) 0.6647(7) 0.7684(7) 0.0346(16) Uani 1 1 d . . . . .
H3 H 0.148344 0.656126 0.838642 0.042 Uiso 1 1 calc R U . . .
C28 C 1.0297(7) 0.8849(6) 0.1014(6) 0.0300(14) Uani 1 1 d . . . . .
H28 H 1.076456 0.888132 0.037336 0.036 Uiso 1 1 calc R U . . .
C14 C 0.1840(9) 0.4524(7) -0.0572(7) 0.0416(18) Uani 1 1 d . . . . .
H14 H 0.109881 0.383197 -0.110412 0.050 Uiso 1 1 calc R U . . .
C29 C 1.1034(7) 0.8824(6) 0.1932(6) 0.0292(14) Uani 1 1 d . . . . .
H29 H 1.201383 0.883897 0.192368 0.035 Uiso 1 1 calc R U . . .
C13 C 0.2999(10) 0.4909(9) -0.1008(7) 0.052(2) Uani 1 1 d . . . . .
H13 H 0.300276 0.461514 -0.184228 0.062 Uiso 0.49(4) 1 calc R U P A 1
H13A H 0.319155 0.438729 -0.179264 0.062 Uiso 0.51(4) 1 calc R U P A 2
C11 C 0.3950(10) 0.6556(9) 0.0987(7) 0.063(3) Uani 1 1 d . . . . .
H11 H 0.459091 0.735463 0.146784 0.075 Uiso 0.49(4) 1 calc R U P A 1
H11A H 0.477438 0.712327 0.151063 0.075 Uiso 0.51(4) 1 calc R U P A 2
C12 C 0.419(4) 0.575(3) -0.020(3) 0.051(6) Uani 0.49(4) 1 d . U P A 1
H12 H 0.511556 0.578410 -0.043857 0.062 Uiso 0.49(4) 1 calc R U P A 1
C31 C 0.5590(11) 0.9472(10) 0.9110(10) 0.066(2) Uani 1 1 d D U . . .
H31B H 0.658008 0.995186 0.943447 0.079 Uiso 0.494(14) 1 calc R U P B 1
H31A H 0.561047 0.883721 0.827213 0.079 Uiso 0.494(14) 1 calc R U P B 1
H31D H 0.633721 0.912156 0.862997 0.079 Uiso 0.506(14) 1 calc R U P B 2
H31C H 0.476014 0.926429 0.853547 0.079 Uiso 0.506(14) 1 calc R U P B 2
C32 C 0.5164(17) 0.8702(14) 0.9785(13) 0.111(5) Uani 1 1 d . U . . .
H32A H 0.420735 0.813685 0.945706 0.134 Uiso 0.494(14) 1 calc R U P B 1
H32B H 0.584193 0.816936 0.972072 0.134 Uiso 0.494(14) 1 calc R U P B 1
H32C H 0.490044 0.777094 0.923634 0.134 Uiso 0.506(14) 1 calc R U P B 2
H32D H 0.592685 0.888836 1.040934 0.134 Uiso 0.506(14) 1 calc R U P B 2
O1 O 0.482(2) 1.041(2) 0.905(2) 0.107(4) Uani 0.494(14) 1 d . U P B 1
O1A O 0.607(2) 1.0809(19) 0.969(2) 0.108(4) Uani 0.506(14) 1 d . U P B 2
C12A C 0.391(4) 0.610(3) -0.027(3) 0.051(6) Uani 0.51(4) 1 d . U P A 2
H12A H 0.446608 0.658421 -0.058892 0.062 Uiso 0.51(4) 1 calc R U P A 2


_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
Bi1 Bi1 2.8722(7) 2_676 ?
Bi1 N2 2.696(5) 2_676 ?
Bi1 N1 2.296(5) . ?
Bi1 N3 2.400(5) . ?
Bi1 N4 2.501(5) 2_676 ?
N2 N1 1.360(7) . ?
N2 C9 1.356(8) . ?
N1 C7 1.369(8) . ?
N3 N4 1.362(7) . ?
N3 C22 1.352(8) . ?
N4 C24 1.349(8) . ?
C9 C10 1.480(9) . ?
C9 C8 1.386(9) . ?
C21 C22 1.478(8) . ?
C21 C20 1.383(9) . ?
C21 C16 1.398(9) . ?
C22 C23 1.390(9) . ?
C5 H5 0.9500 . ?
C5 C4 1.404(10) . ?
C5 C6 1.393(9) . ?
C24 C25 1.482(8) . ?
C24 C23 1.391(9) . ?
C25 C26 1.383(10) . ?
C25 C30 1.402(9) . ?
C10 C15 1.382(10) . ?
C10 C11 1.386(10) . ?
C20 H20 0.9500 . ?
C20 C19 1.387(10) . ?
C8 H8 0.9500 . ?
C8 C7 1.380(9) . ?
C7 C6 1.479(9) . ?
C23 H23 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.389(10) . ?
C4 H4 0.9500 . ?
C4 C3 1.382(10) . ?
C26 H26 0.9500 . ?
C26 C27 1.389(9) . ?
C30 H30 0.9500 . ?
C30 C29 1.382(9) . ?
C1 H1 0.9500 . ?
C1 C6 1.390(9) . ?
C1 C2 1.400(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(10) . ?
C19 H19 0.9500 . ?
C19 C18 1.376(10) . ?
C15 H15 0.9500 . ?
C15 C14 1.385(11) . ?
C27 H27 0.9500 . ?
C27 C28 1.380(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(11) . ?
C18 H18 0.9500 . ?
C3 H3 0.9500 . ?
C28 H28 0.9500 . ?
C28 C29 1.373(10) . ?
C14 H14 0.9500 . ?
C14 C13 1.356(12) . ?
C29 H29 0.9500 . ?
C13 H13 0.9500 . ?
C13 H13A 0.9500 . ?
C13 C12 1.40(4) . ?
C13 C12A 1.40(4) . ?
C11 H11 0.9500 . ?
C11 H11A 0.9500 . ?
C11 C12 1.43(4) . ?
C11 C12A 1.42(4) . ?
C12 H12 0.9500 . ?
C31 H31B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31D 0.9900 . ?
C31 H31C 0.9900 . ?
C31 C32 1.535(17) . ?
C31 O1 1.51(2) . ?
C31 O1A 1.41(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 H32C 0.9900 . ?
C32 H32D 0.9900 . ?
C32 O1 1.37(2) 2_677 ?
C32 O1A 1.48(2) 2_677 ?
C12A H12A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Bi1 Bi1 66.86(11) 2_676 2_676 ?
N1 Bi1 Bi1 77.41(12) . 2_676 ?
N1 Bi1 N2 143.71(16) . 2_676 ?
N1 Bi1 N3 84.17(18) . . ?
N1 Bi1 N4 82.39(18) . 2_676 ?
N3 Bi1 Bi1 71.58(12) . 2_676 ?
N3 Bi1 N2 90.27(16) . 2_676 ?
N3 Bi1 N4 142.99(16) . 2_676 ?
N4 Bi1 Bi1 71.89(11) 2_676 2_676 ?
N4 Bi1 N2 80.79(16) 2_676 2_676 ?
N1 N2 Bi1 102.0(3) . 2_676 ?
C9 N2 Bi1 152.2(4) . 2_676 ?
C9 N2 N1 105.7(5) . . ?
N2 N1 Bi1 111.7(3) . . ?
N2 N1 C7 110.2(5) . . ?
C7 N1 Bi1 135.2(4) . . ?
N4 N3 Bi1 111.8(3) . . ?
C22 N3 Bi1 136.8(4) . . ?
C22 N3 N4 108.3(4) . . ?
N3 N4 Bi1 103.1(3) . 2_676 ?
C24 N4 Bi1 148.3(4) . 2_676 ?
C24 N4 N3 108.2(5) . . ?
N2 C9 C10 121.1(5) . . ?
N2 C9 C8 110.9(5) . . ?
C8 C9 C10 127.8(6) . . ?
C20 C21 C22 121.0(6) . . ?
C20 C21 C16 118.9(6) . . ?
C16 C21 C22 120.1(6) . . ?
N3 C22 C21 120.8(5) . . ?
N3 C22 C23 109.1(5) . . ?
C23 C22 C21 129.9(6) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.3(6) . . ?
N4 C24 C25 122.2(6) . . ?
N4 C24 C23 109.3(5) . . ?
C23 C24 C25 128.4(6) . . ?
C26 C25 C24 121.2(6) . . ?
C26 C25 C30 118.9(6) . . ?
C30 C25 C24 119.9(6) . . ?
C15 C10 C9 120.2(6) . . ?
C15 C10 C11 118.5(7) . . ?
C11 C10 C9 121.1(6) . . ?
C21 C20 H20 119.7 . . ?
C21 C20 C19 120.5(6) . . ?
C19 C20 H20 119.7 . . ?
C9 C8 H8 127.3 . . ?
C7 C8 C9 105.4(5) . . ?
C7 C8 H8 127.3 . . ?
N1 C7 C8 107.7(5) . . ?
N1 C7 C6 122.1(6) . . ?
C8 C7 C6 130.0(6) . . ?
C22 C23 C24 105.1(5) . . ?
C22 C23 H23 127.4 . . ?
C24 C23 H23 127.4 . . ?
C21 C16 H16 120.0 . . ?
C17 C16 C21 120.1(7) . . ?
C17 C16 H16 120.0 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.4(6) . . ?
C3 C4 H4 119.8 . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.1(6) . . ?
C27 C26 H26 120.0 . . ?
C25 C30 H30 119.8 . . ?
C29 C30 C25 120.3(6) . . ?
C29 C30 H30 119.8 . . ?
C6 C1 H1 119.7 . . ?
C6 C1 C2 120.5(6) . . ?
C2 C1 H1 119.7 . . ?
C5 C6 C7 119.1(6) . . ?
C1 C6 C5 120.1(6) . . ?
C1 C6 C7 120.8(6) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.1(7) . . ?
C3 C2 H2 120.5 . . ?
C20 C19 H19 119.7 . . ?
C18 C19 C20 120.6(7) . . ?
C18 C19 H19 119.7 . . ?
C10 C15 H15 119.6 . . ?
C10 C15 C14 120.8(7) . . ?
C14 C15 H15 119.6 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.5(7) . . ?
C28 C27 H27 119.7 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(6) . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.4(6) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C4 C3 C2 120.5(7) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.8(6) . . ?
C29 C28 H28 120.1 . . ?
C15 C14 H14 119.6 . . ?
C13 C14 C15 120.8(8) . . ?
C13 C14 H14 119.6 . . ?
C30 C29 H29 119.8 . . ?
C28 C29 C30 120.4(6) . . ?
C28 C29 H29 119.8 . . ?
C14 C13 H13 120.6 . . ?
C14 C13 H13A 121.0 . . ?
C14 C13 C12 118.7(15) . . ?
C14 C13 C12A 118.1(15) . . ?
C12 C13 H13 120.6 . . ?
C12A C13 H13A 121.0 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 H11A 120.7 . . ?
C10 C11 C12 119.1(16) . . ?
C10 C11 C12A 118.7(16) . . ?
C12 C11 H11 120.5 . . ?
C12A C11 H11A 120.7 . . ?
C13 C12 C11 117(3) . . ?
C13 C12 H12 121.7 . . ?
C11 C12 H12 121.7 . . ?
H31B C31 H31A 106.3 . . ?
H31D C31 H31C 106.5 . . ?
C32 C31 H31B 106.1 . . ?
C32 C31 H31A 106.1 . . ?
C32 C31 H31D 106.6 . . ?
C32 C31 H31C 106.6 . . ?
O1 C31 H31B 106.1 . . ?
O1 C31 H31A 106.1 . . ?
O1 C31 C32 124.8(13) . . ?
O1A C31 H31D 106.6 . . ?
O1A C31 H31C 106.6 . . ?
O1A C31 C32 123.0(14) . . ?
C31 C32 H32A 110.6 . . ?
C31 C32 H32B 110.6 . . ?
C31 C32 H32C 111.7 . . ?
C31 C32 H32D 111.7 . . ?
H32A C32 H32B 108.7 . . ?
H32C C32 H32D 109.4 . . ?
O1 C32 C31 105.7(15) 2_677 . ?
O1 C32 H32A 110.6 2_677 . ?
O1 C32 H32B 110.6 2_677 . ?
O1 C32 O1A 55.4(12) 2_677 2_677 ?
O1A C32 C31 100.5(14) 2_677 . ?
O1A C32 H32C 111.7 2_677 . ?
O1A C32 H32D 111.7 2_677 . ?
C32 O1 C31 105.1(17) 2_677 . ?
C31 O1A C32 104.8(15) . 2_677 ?
C13 C12A C11 117(2) . . ?
C13 C12A H12A 121.4 . . ?
C11 C12A H12A 121.4 . . ?

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
Bi1 N2 N1 Bi1 -13.6(4) 2_676 . . . ?
Bi1 N2 N1 C7 -177.5(4) 2_676 . . . ?
Bi1 N2 C9 C10 1.5(12) 2_676 . . . ?
Bi1 N2 C9 C8 176.9(6) 2_676 . . . ?
Bi1 N1 C7 C8 -160.3(4) . . . . ?
Bi1 N1 C7 C6 15.4(9) . . . . ?
Bi1 N3 N4 Bi1 -12.7(4) . . . 2_676 ?
Bi1 N3 N4 C24 162.4(4) . . . . ?
Bi1 N3 C22 C21 28.0(9) . . . . ?
Bi1 N3 C22 C23 -156.2(5) . . . . ?
Bi1 N4 C24 C25 -12.4(12) 2_676 . . . ?
Bi1 N4 C24 C23 171.6(6) 2_676 . . . ?
N2 N1 C7 C8 -1.8(7) . . . . ?
N2 N1 C7 C6 173.9(5) . . . . ?
N2 C9 C10 C15 -160.4(6) . . . . ?
N2 C9 C10 C11 25.9(10) . . . . ?
N2 C9 C8 C7 -1.5(7) . . . . ?
N1 N2 C9 C10 -174.9(5) . . . . ?
N1 N2 C9 C8 0.4(7) . . . . ?
N1 C7 C6 C5 -146.8(6) . . . . ?
N1 C7 C6 C1 31.2(9) . . . . ?
N3 N4 C24 C25 176.6(5) . . . . ?
N3 N4 C24 C23 0.6(7) . . . . ?
N3 C22 C23 C24 -0.7(7) . . . . ?
N4 N3 C22 C21 -174.7(5) . . . . ?
N4 N3 C22 C23 1.1(7) . . . . ?
N4 C24 C25 C26 -24.8(9) . . . . ?
N4 C24 C25 C30 158.2(6) . . . . ?
N4 C24 C23 C22 0.1(7) . . . . ?
C9 N2 N1 Bi1 164.7(4) . . . . ?
C9 N2 N1 C7 0.8(6) . . . . ?
C9 C10 C15 C14 -175.3(6) . . . . ?
C9 C10 C11 C12 161.1(19) . . . . ?
C9 C10 C11 C12A -171.8(18) . . . . ?
C9 C8 C7 N1 1.9(7) . . . . ?
C9 C8 C7 C6 -173.3(6) . . . . ?
C21 C22 C23 C24 174.6(6) . . . . ?
C21 C20 C19 C18 -0.2(10) . . . . ?
C21 C16 C17 C18 -0.5(11) . . . . ?
C22 N3 N4 Bi1 -176.2(4) . . . 2_676 ?
C22 N3 N4 C24 -1.1(7) . . . . ?
C22 C21 C20 C19 -177.3(6) . . . . ?
C22 C21 C16 C17 177.6(6) . . . . ?
C5 C4 C3 C2 1.1(10) . . . . ?
C24 C25 C26 C27 -177.3(6) . . . . ?
C24 C25 C30 C29 176.7(6) . . . . ?
C25 C24 C23 C22 -175.6(6) . . . . ?
C25 C26 C27 C28 0.7(10) . . . . ?
C25 C30 C29 C28 0.6(10) . . . . ?
C10 C9 C8 C7 173.5(6) . . . . ?
C10 C15 C14 C13 1.8(12) . . . . ?
C10 C11 C12 C13 26(3) . . . . ?
C10 C11 C12A C13 -27(3) . . . . ?
C20 C21 C22 N3 -137.9(6) . . . . ?
C20 C21 C22 C23 47.2(10) . . . . ?
C20 C21 C16 C17 -1.2(10) . . . . ?
C20 C19 C18 C17 -1.5(10) . . . . ?
C8 C9 C10 C15 25.0(10) . . . . ?
C8 C9 C10 C11 -148.6(9) . . . . ?
C8 C7 C6 C5 27.8(10) . . . . ?
C8 C7 C6 C1 -154.2(7) . . . . ?
C23 C24 C25 C26 150.4(7) . . . . ?
C23 C24 C25 C30 -26.7(10) . . . . ?
C16 C21 C22 N3 43.3(9) . . . . ?
C16 C21 C22 C23 -131.5(7) . . . . ?
C16 C21 C20 C19 1.5(10) . . . . ?
C16 C17 C18 C19 1.8(11) . . . . ?
C4 C5 C6 C7 176.5(6) . . . . ?
C4 C5 C6 C1 -1.5(9) . . . . ?
C26 C25 C30 C29 -0.4(9) . . . . ?
C26 C27 C28 C29 -0.6(10) . . . . ?
C30 C25 C26 C27 -0.2(10) . . . . ?
C1 C2 C3 C4 0.8(10) . . . . ?
C6 C5 C4 C3 -0.7(10) . . . . ?
C6 C1 C2 C3 -3.1(10) . . . . ?
C2 C1 C6 C5 3.4(10) . . . . ?
C2 C1 C6 C7 -174.6(6) . . . . ?
C15 C10 C11 C12 -13(2) . . . . ?
C15 C10 C11 C12A 14(2) . . . . ?
C15 C14 C13 C12 12(2) . . . . ?
C15 C14 C13 C12A -15(2) . . . . ?
C27 C28 C29 C30 -0.1(10) . . . . ?
C14 C13 C12 C11 -26(3) . . . . ?
C14 C13 C12A C11 27(3) . . . . ?
C11 C10 C15 C14 -1.5(12) . . . . ?
C32 C31 O1 C32 58(2) . . . 2_677 ?
C32 C31 O1A C32 -67(2) . . . 2_677 ?
O1 C31 C32 O1 -58(2) . . . 2_677 ?
O1A C31 C32 O1A 65(2) . . . 2_677 ?

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

data_exp_1218
_database_code_depnum_ccdc_archive 'CCDC 2243050'
loop_
_audit_author_name
_audit_author_address
'Peter Junk'
;James Cook University
Australia
;
_audit_update_record             
;
2023-02-19 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_audit_creation_date             2023-02-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C62 H70 Bi2 F10 N4'
_chemical_formula_sum            'C62 H70 Bi2 F10 N4'
_chemical_formula_weight         1479.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         PrCHNOF
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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.32528(13)
_cell_length_b                   12.25378(12)
_cell_length_c                   12.54848(12)
_cell_angle_alpha                105.9880(9)
_cell_angle_beta                 106.5627(10)
_cell_angle_gamma                102.5770(9)
_cell_volume                     1519.42(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    31253
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      33.8980
_cell_measurement_theta_min      3.4190
_shelx_estimated_absorpt_T_max   0.592
_shelx_estimated_absorpt_T_min   0.273
_exptl_absorpt_coefficient_mu    5.854
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             726
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49963
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.886
_diffrn_reflns_theta_min         3.427
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  38.00   0.50    6.23    --   12.96 -82.00 -78.00  160
  2  ω    -23.00  46.00   0.50    6.23    --   12.96 -99.00  30.00  138
  3  ω    -42.00  11.00   0.50    6.23    --  -13.74 -82.00 -78.00  106
  4  ω    -60.00  25.00   0.50    6.23    --   12.96 -37.00-120.00  170
  5  ω     -2.00  85.00   0.50    6.23    --   12.96  57.00-180.00  174
  6  ω     41.00  86.00   0.50    6.23    --   12.96 178.00-120.00   90
  7  ω     41.00  86.00   0.50    6.23    --   12.96 178.00 -30.00   90
  8  ω     41.00  86.00   0.50    6.23    --   12.96 178.00  60.00   90
  9  ω     -2.00  85.00   0.50    6.23    --   12.96  57.00  60.00  174
 10  ω     41.00  86.00   0.50    6.23    --   12.96 178.00-150.00   90
 11  ω    -29.00   1.00   0.50    6.23    --  -13.74  57.00   0.00   60
 12  ω    -39.00  21.00   0.50    6.23    --  -13.74  82.00  43.00  120
 13  ω    -85.00   1.00   0.50    6.23    --  -13.74 -57.00 -60.00  172
 14  ω    -85.00   9.00   0.50    6.23    --  -13.74 -77.00-120.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0567674000
_diffrn_orient_matrix_UB_12      0.0213859000
_diffrn_orient_matrix_UB_13      0.0522067000
_diffrn_orient_matrix_UB_21      0.0096474000
_diffrn_orient_matrix_UB_22      -0.0566091000
_diffrn_orient_matrix_UB_23      -0.0167690000
_diffrn_orient_matrix_UB_31      0.0380278000
_diffrn_orient_matrix_UB_32      0.0195382000
_diffrn_orient_matrix_UB_33      -0.0314849000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9832
_reflns_number_total             10875
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.146
_refine_diff_density_min         -1.049
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         10875
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0306P)²+0.1373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0557
_refine_ls_wR_factor_ref         0.0570
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H18A,H18B,H18C} of C18, {H12A,H12B,H12C} of C12, {H25A,
  H25B,H25C} of C25, {H11A,H11B,H11C} of C11
 At 1.5 times of:
  {H2A,H2B,H2C} of C2, {H1A,H1B,H1C} of C1, {H17A,H17B,H17C} of C17, {H24A,
  H24B,H24C} of C24
2. Rigid bond restraints
 C20, C19
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C25, C23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C20, C21
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C20 \\sim C19: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C25 \\sim C23: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C20 \\sim C21: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
4.a Ternary CH refined with riding coordinates:
 C10(H10), C16(H16), C23(H23), C3(H3)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C5(H5), C21(H21), C19(H19), C20(H20)
4.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1A,H1B,H1C), C24(H24A,H24B,H24C), C17(H17A,H17B,H17C),
 C18(H18A,H18B,H18C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C25(H25A,H25B,
 H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.49341(2) 0.37399(2) 0.45496(2) 0.01430(3) Uani 1 1 d . . . . .
F5 F 0.23556(18) 0.46895(14) 0.5076(2) 0.0581(6) Uani 1 1 d . . . . .
N1 N 0.41411(19) 0.39895(16) 0.26340(15) 0.0187(3) Uani 1 1 d . . . . .
N2 N 0.4628(2) 0.60641(16) 0.33779(16) 0.0242(4) Uani 1 1 d . . . . .
F1 F 0.30417(18) 0.10713(14) 0.3336(2) 0.0568(6) Uani 1 1 d . . . . .
C13 C 0.4227(2) 0.5026(2) 0.2505(2) 0.0219(4) Uani 1 1 d . . . . .
F2 F 0.0564(2) -0.01437(15) 0.2881(3) 0.0702(7) Uani 1 1 d . . . . .
F3 F -0.1025(2) 0.10543(18) 0.3518(3) 0.0807(9) Uani 1 1 d . . . . .
C26 C 0.2797(2) 0.29185(19) 0.4231(2) 0.0197(4) Uani 1 1 d . . . . .
C31 C 0.1953(3) 0.3484(2) 0.4518(3) 0.0318(6) Uani 1 1 d . . . . .
C14 C 0.4654(4) 0.7110(2) 0.3058(2) 0.0382(7) Uani 1 1 d . . . . .
C9 C 0.3638(3) 0.29188(19) 0.15971(19) 0.0227(4) Uani 1 1 d . . . . .
C8 C 0.4510(3) 0.2350(2) 0.1283(2) 0.0318(6) Uani 1 1 d . . . . .
F4 F -0.0107(2) 0.3479(2) 0.4608(3) 0.0944(12) Uani 1 1 d . . . . .
C10 C 0.5962(4) 0.2927(3) 0.1874(3) 0.0489(8) Uani 1 1 d . . . . .
H10 H 0.613775 0.366715 0.253332 0.059 Uiso 1 1 calc R U . . .
C27 C 0.2286(3) 0.1689(2) 0.3678(3) 0.0307(5) Uani 1 1 d . . . . .
C22 C 0.3653(5) 0.7629(3) 0.3126(3) 0.0539(11) Uani 1 1 d . . . . .
C4 C 0.2289(3) 0.2412(3) 0.0954(2) 0.0383(7) Uani 1 1 d . . . . .
C15 C 0.5640(4) 0.7602(2) 0.2714(3) 0.0508(10) Uani 1 1 d . . . . .
C29 C 0.0207(3) 0.1659(3) 0.3756(3) 0.0470(8) Uani 1 1 d . . . . .
C16 C 0.6714(4) 0.7095(3) 0.2645(3) 0.0552(10) Uani 1 1 d . . . . .
H16 H 0.670167 0.652762 0.306412 0.066 Uiso 1 1 calc R U . . .
C23 C 0.2615(4) 0.7172(4) 0.3563(3) 0.0694(11) Uani 1 1 d . U . . .
H23 H 0.277904 0.650374 0.379812 0.083 Uiso 1 1 calc R U . . .
C28 C 0.1021(3) 0.1054(2) 0.3443(3) 0.0417(7) Uani 1 1 d . . . . .
C30 C 0.0675(3) 0.2890(3) 0.4288(4) 0.0482(9) Uani 1 1 d . . . . .
C7 C 0.3987(4) 0.1235(2) 0.0352(3) 0.0458(8) Uani 1 1 d . . . . .
H7 H 0.454324 0.083503 0.014055 0.055 Uiso 1 1 calc R U . . .
C3 C 0.1330(3) 0.3052(4) 0.1191(3) 0.0509(9) Uani 1 1 d . . . . .
H3 H 0.173513 0.364072 0.200736 0.061 Uiso 1 1 calc R U . . .
C6 C 0.2671(5) 0.0720(3) -0.0255(3) 0.0591(11) Uani 1 1 d . . . . .
H6 H 0.234207 -0.003037 -0.085943 0.071 Uiso 1 1 calc R U . . .
C5 C 0.1838(4) 0.1307(3) 0.0025(3) 0.0598(11) Uani 1 1 d . . . . .
H5 H 0.095050 0.095987 -0.041480 0.072 Uiso 1 1 calc R U . . .
C2 C 0.0044(4) 0.2227(5) 0.1071(4) 0.0825(15) Uani 1 1 d . . . . .
H2A H -0.045127 0.175219 0.024497 0.124 Uiso 1 1 calc R U . . .
H2B H -0.043703 0.269874 0.138531 0.124 Uiso 1 1 calc R U . . .
H2C H 0.021024 0.170870 0.150644 0.124 Uiso 1 1 calc R U . . .
C1 C 0.1042(5) 0.3727(5) 0.0340(4) 0.0841(16) Uani 1 1 d . . . . .
H1A H 0.182698 0.433128 0.048123 0.126 Uiso 1 1 calc R U . . .
H1B H 0.040638 0.409900 0.047187 0.126 Uiso 1 1 calc R U . . .
H1C H 0.071008 0.317502 -0.046846 0.126 Uiso 1 1 calc R U . . .
C21 C 0.3671(7) 0.8617(3) 0.2781(4) 0.0867(12) Uani 1 1 d . U . . .
H21 H 0.301903 0.896156 0.279994 0.104 Uiso 1 1 calc R U . . .
C19 C 0.5596(7) 0.8611(3) 0.2384(3) 0.0861(12) Uani 1 1 d . U . . .
H19 H 0.623899 0.895592 0.214136 0.103 Uiso 1 1 calc R U . . .
C24 C 0.2671(7) 0.8143(5) 0.4654(4) 0.0915(19) Uani 1 1 d . . . . .
H24A H 0.353882 0.845961 0.523956 0.137 Uiso 1 1 calc R U . . .
H24B H 0.207804 0.780706 0.498212 0.137 Uiso 1 1 calc R U . . .
H24C H 0.243212 0.877456 0.442740 0.137 Uiso 1 1 calc R U . . .
C17 C 0.6500(6) 0.6392(4) 0.1338(3) 0.0730(13) Uani 1 1 d . . . . .
H17A H 0.567679 0.576411 0.097627 0.110 Uiso 1 1 calc R U . . .
H17B H 0.718384 0.604925 0.132307 0.110 Uiso 1 1 calc R U . . .
H17C H 0.650785 0.692668 0.090497 0.110 Uiso 1 1 calc R U . . .
C20 C 0.4604(7) 0.9084(4) 0.2421(4) 0.0883(11) Uani 1 1 d . U . . .
H20 H 0.458153 0.974173 0.219153 0.106 Uiso 1 1 calc R U . . .
C18 C 0.8053(6) 0.8038(4) 0.3237(5) 0.098(2) Uani 1 1 d . . . . .
H18A H 0.812724 0.855467 0.279045 0.118 Uiso 1 1 calc R U . . .
H18B H 0.870719 0.765224 0.326089 0.118 Uiso 1 1 calc R U . . .
H18C H 0.816992 0.850364 0.403508 0.118 Uiso 1 1 calc R U . . .
C11 C 0.6538(5) 0.3270(6) 0.0998(6) 0.099(2) Uani 1 1 d . . . . .
H11A H 0.652831 0.255980 0.042559 0.119 Uiso 1 1 calc R U . . .
H11B H 0.741750 0.379738 0.142769 0.119 Uiso 1 1 calc R U . . .
H11C H 0.602851 0.366903 0.059365 0.119 Uiso 1 1 calc R U . . .
C12 C 0.6666(6) 0.2182(6) 0.2369(5) 0.103(2) Uani 1 1 d . . . . .
H12A H 0.672081 0.157170 0.173191 0.123 Uiso 1 1 calc R U . . .
H12B H 0.620661 0.181369 0.278107 0.123 Uiso 1 1 calc R U . . .
H12C H 0.752739 0.267909 0.291526 0.123 Uiso 1 1 calc R U . . .
C25 C 0.1270(5) 0.6712(5) 0.2603(4) 0.0943(13) Uani 1 1 d . U . . .
H25A H 0.122992 0.607079 0.193538 0.113 Uiso 1 1 calc R U . . .
H25B H 0.109262 0.735063 0.235104 0.113 Uiso 1 1 calc R U . . .
H25C H 0.063493 0.642277 0.291489 0.113 Uiso 1 1 calc R U . . .
H13 H 0.395(3) 0.503(3) 0.159(3) 0.025(7) Uiso 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
Bi1 Bi1 2.93542(13) 2_666 ?
Bi1 N1 2.4438(18) . ?
Bi1 N2 2.4363(18) 2_666 ?
Bi1 C26 2.280(2) . ?
F5 C31 1.355(3) . ?
N1 C13 1.311(3) . ?
N1 C9 1.432(3) . ?
N2 C13 1.312(3) . ?
N2 C14 1.442(3) . ?
F1 C27 1.343(3) . ?
C13 H13 1.10(3) . ?
F2 C28 1.345(3) . ?
F3 C29 1.332(3) . ?
C26 C31 1.367(3) . ?
C26 C27 1.379(3) . ?
C31 C30 1.377(4) . ?
C14 C22 1.427(5) . ?
C14 C15 1.385(5) . ?
C9 C8 1.409(4) . ?
C9 C4 1.407(4) . ?
C8 C10 1.505(5) . ?
C8 C7 1.399(4) . ?
F4 C30 1.337(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.534(6) . ?
C10 C12 1.484(6) . ?
C27 C28 1.375(4) . ?
C22 C23 1.498(7) . ?
C22 C21 1.392(4) . ?
C4 C3 1.520(5) . ?
C4 C5 1.394(4) . ?
C15 C16 1.495(6) . ?
C15 C19 1.414(4) . ?
C29 C28 1.377(4) . ?
C29 C30 1.377(4) . ?
C16 H16 0.9800 . ?
C16 C17 1.548(5) . ?
C16 C18 1.519(6) . ?
C23 H23 0.9800 . ?
C23 C24 1.521(5) . ?
C23 C25 1.515(6) . ?
C7 H7 0.9300 . ?
C7 C6 1.370(6) . ?
C3 H3 0.9800 . ?
C3 C2 1.521(6) . ?
C3 C1 1.529(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.369(6) . ?
C5 H5 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C21 H21 0.9300 . ?
C21 C20 1.342(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(8) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C20 H20 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
N1 Bi1 Bi1 81.76(4) . 2_666 ?
N2 Bi1 Bi1 83.12(4) 2_666 2_666 ?
N2 Bi1 N1 162.05(7) 2_666 . ?
C26 Bi1 Bi1 96.96(5) . 2_666 ?
C26 Bi1 N1 85.90(7) . . ?
C26 Bi1 N2 86.38(8) . 2_666 ?
C13 N1 Bi1 124.47(14) . . ?
C13 N1 C9 119.33(19) . . ?
C9 N1 Bi1 116.05(13) . . ?
C13 N2 Bi1 123.06(15) . 2_666 ?
C13 N2 C14 117.21(19) . . ?
C14 N2 Bi1 119.30(14) . 2_666 ?
N1 C13 N2 125.3(2) . . ?
N1 C13 H13 117.7(15) . . ?
N2 C13 H13 117.0(15) . . ?
C31 C26 Bi1 128.56(16) . . ?
C31 C26 C27 115.6(2) . . ?
C27 C26 Bi1 115.85(17) . . ?
F5 C31 C26 120.6(2) . . ?
F5 C31 C30 115.9(2) . . ?
C26 C31 C30 123.5(2) . . ?
C22 C14 N2 118.0(3) . . ?
C15 C14 N2 120.5(3) . . ?
C15 C14 C22 121.4(3) . . ?
C8 C9 N1 118.7(2) . . ?
C4 C9 N1 120.1(2) . . ?
C4 C9 C8 121.1(2) . . ?
C9 C8 C10 122.3(2) . . ?
C7 C8 C9 117.9(3) . . ?
C7 C8 C10 119.8(3) . . ?
C8 C10 H10 107.7 . . ?
C8 C10 C11 110.5(3) . . ?
C11 C10 H10 107.7 . . ?
C12 C10 C8 114.8(4) . . ?
C12 C10 H10 107.7 . . ?
C12 C10 C11 108.0(4) . . ?
F1 C27 C26 119.2(2) . . ?
F1 C27 C28 117.7(2) . . ?
C28 C27 C26 123.1(2) . . ?
C14 C22 C23 123.2(3) . . ?
C21 C22 C14 117.3(4) . . ?
C21 C22 C23 119.4(4) . . ?
C9 C4 C3 122.6(2) . . ?
C5 C4 C9 117.9(3) . . ?
C5 C4 C3 119.5(3) . . ?
C14 C15 C16 123.0(3) . . ?
C14 C15 C19 117.9(4) . . ?
C19 C15 C16 119.1(4) . . ?
F3 C29 C28 119.9(3) . . ?
F3 C29 C30 120.8(3) . . ?
C30 C29 C28 119.2(3) . . ?
C15 C16 H16 107.6 . . ?
C15 C16 C17 111.3(4) . . ?
C15 C16 C18 113.2(4) . . ?
C17 C16 H16 107.6 . . ?
C18 C16 H16 107.6 . . ?
C18 C16 C17 109.3(3) . . ?
C22 C23 H23 108.0 . . ?
C22 C23 C24 110.6(4) . . ?
C22 C23 C25 112.0(4) . . ?
C24 C23 H23 108.0 . . ?
C25 C23 H23 108.0 . . ?
C25 C23 C24 110.0(4) . . ?
F2 C28 C27 120.7(3) . . ?
F2 C28 C29 119.9(3) . . ?
C27 C28 C29 119.4(2) . . ?
C31 C30 C29 119.2(3) . . ?
F4 C30 C31 121.4(3) . . ?
F4 C30 C29 119.4(3) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 C8 121.2(3) . . ?
C6 C7 H7 119.4 . . ?
C4 C3 H3 108.1 . . ?
C4 C3 C2 114.1(4) . . ?
C4 C3 C1 110.1(3) . . ?
C2 C3 H3 108.1 . . ?
C2 C3 C1 108.3(3) . . ?
C1 C3 H3 108.1 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.6(4) . . ?
C6 C5 H5 119.2 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C22 C21 H21 119.1 . . ?
C20 C21 C22 121.7(5) . . ?
C20 C21 H21 119.1 . . ?
C15 C19 H19 119.9 . . ?
C20 C19 C15 120.2(5) . . ?
C20 C19 H19 119.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C21 C20 C19 121.4(4) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
Bi1 N1 C13 N2 -7.1(4) . . . . ?
Bi1 N1 C9 C8 -69.9(2) . . . . ?
Bi1 N1 C9 C4 106.2(2) . . . . ?
Bi1 N2 C13 N1 -7.5(4) 2_666 . . . ?
Bi1 N2 C14 C22 -68.7(3) 2_666 . . . ?
Bi1 N2 C14 C15 110.2(2) 2_666 . . . ?
Bi1 C26 C31 F5 -0.5(4) . . . . ?
Bi1 C26 C31 C30 -179.5(3) . . . . ?
Bi1 C26 C27 F1 -2.1(3) . . . . ?
Bi1 C26 C27 C28 178.7(3) . . . . ?
F5 C31 C30 F4 -0.4(6) . . . . ?
F5 C31 C30 C29 -178.0(4) . . . . ?
N1 C9 C8 C10 -10.1(4) . . . . ?
N1 C9 C8 C7 172.8(2) . . . . ?
N1 C9 C4 C3 9.8(4) . . . . ?
N1 C9 C4 C5 -173.6(3) . . . . ?
N2 C14 C22 C23 2.7(4) . . . . ?
N2 C14 C22 C21 -178.2(3) . . . . ?
N2 C14 C15 C16 0.4(4) . . . . ?
N2 C14 C15 C19 178.6(3) . . . . ?
F1 C27 C28 F2 -0.5(5) . . . . ?
F1 C27 C28 C29 -178.5(3) . . . . ?
C13 N1 C9 C8 105.8(3) . . . . ?
C13 N1 C9 C4 -78.1(3) . . . . ?
C13 N2 C14 C22 104.1(3) . . . . ?
C13 N2 C14 C15 -77.0(3) . . . . ?
F3 C29 C28 F2 1.0(6) . . . . ?
F3 C29 C28 C27 179.0(4) . . . . ?
F3 C29 C30 C31 -179.8(4) . . . . ?
F3 C29 C30 F4 2.5(7) . . . . ?
C26 C31 C30 F4 178.7(3) . . . . ?
C26 C31 C30 C29 1.0(6) . . . . ?
C26 C27 C28 F2 178.7(3) . . . . ?
C26 C27 C28 C29 0.7(5) . . . . ?
C31 C26 C27 F1 178.1(3) . . . . ?
C31 C26 C27 C28 -1.1(4) . . . . ?
C14 N2 C13 N1 -180.0(3) . . . . ?
C14 C22 C23 C24 119.7(4) . . . . ?
C14 C22 C23 C25 -117.2(4) . . . . ?
C14 C22 C21 C20 -1.4(6) . . . . ?
C14 C15 C16 C17 103.7(3) . . . . ?
C14 C15 C16 C18 -132.7(3) . . . . ?
C14 C15 C19 C20 0.7(6) . . . . ?
C9 N1 C13 N2 177.6(2) . . . . ?
C9 C8 C10 C11 -110.7(4) . . . . ?
C9 C8 C10 C12 126.8(4) . . . . ?
C9 C8 C7 C6 1.4(4) . . . . ?
C9 C4 C3 C2 -143.3(3) . . . . ?
C9 C4 C3 C1 94.8(4) . . . . ?
C9 C4 C5 C6 0.5(5) . . . . ?
C8 C9 C4 C3 -174.2(3) . . . . ?
C8 C9 C4 C5 2.4(4) . . . . ?
C8 C7 C6 C5 1.5(5) . . . . ?
C10 C8 C7 C6 -175.8(3) . . . . ?
C27 C26 C31 F5 179.3(3) . . . . ?
C27 C26 C31 C30 0.3(4) . . . . ?
C22 C14 C15 C16 179.2(3) . . . . ?
C22 C14 C15 C19 -2.6(5) . . . . ?
C22 C21 C20 C19 -0.4(7) . . . . ?
C4 C9 C8 C10 173.8(3) . . . . ?
C4 C9 C8 C7 -3.3(4) . . . . ?
C15 C14 C22 C23 -176.2(3) . . . . ?
C15 C14 C22 C21 2.9(5) . . . . ?
C15 C19 C20 C21 0.8(7) . . . . ?
C16 C15 C19 C20 178.9(4) . . . . ?
C23 C22 C21 C20 177.8(4) . . . . ?
C28 C29 C30 C31 -1.4(6) . . . . ?
C28 C29 C30 F4 -179.1(4) . . . . ?
C30 C29 C28 F2 -177.4(4) . . . . ?
C30 C29 C28 C27 0.6(6) . . . . ?
C7 C8 C10 C11 66.4(4) . . . . ?
C7 C8 C10 C12 -56.1(4) . . . . ?
C7 C6 C5 C4 -2.5(6) . . . . ?
C3 C4 C5 C6 177.2(3) . . . . ?
C5 C4 C3 C2 40.2(4) . . . . ?
C5 C4 C3 C1 -81.7(4) . . . . ?
C21 C22 C23 C24 -59.4(5) . . . . ?
C21 C22 C23 C25 63.7(5) . . . . ?
C19 C15 C16 C17 -74.5(4) . . . . ?
C19 C15 C16 C18 49.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.809
# start Validation Reply Form
_vrf_PLAT910_exp_1218            
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         12 Note  
RESPONSE: Low-angle reflections rejected because of beam stop and
high background scattering.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_p-1
_database_code_depnum_ccdc_archive 'CCDC 2243051'
loop_
_audit_author_name
_audit_author_address
'Peter Junk'
;James Cook University
Australia
;
_audit_update_record             
;
2023-02-19 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_audit_creation_date             2023-02-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C56 H70 Bi F5 N4'
_chemical_formula_sum            'C56 H70 Bi F5 N4'
_chemical_formula_weight         1103.14
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.980(2)
_cell_length_b                   12.580(3)
_cell_length_c                   21.130(4)
_cell_angle_alpha                73.17(3)
_cell_angle_beta                 77.93(3)
_cell_angle_gamma                70.19(3)
_cell_volume                     2608.3(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9171
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.725
_exptl_absorpt_coefficient_mu    3.437
_exptl_absorpt_correction_T_max  0.7
_exptl_absorpt_correction_T_min  0.5
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XDS(Kabsch, 1993)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            45146
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         1.015
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'MX1 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8670
_reflns_number_total             9171
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.225
_refine_diff_density_min         -1.039
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         9171
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0214
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+1.2918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0511
_refine_ls_wR_factor_ref         0.0520
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C49A \\sim C49: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.01 within 2A
C20 \\sim C21 \\sim C22: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.01 within 2A
3. Others
 Fixed Sof: H48(0.6) H48A(0.4) C50(0.6) H50A(0.6) H50B(0.6) H50C(0.6) C49(0.8)
 H49A(0.9) H49B(0.9) H49C(0.9) C50A(0.4) H50D(0.4) H50E(0.4) H50F(0.4)
 C49A(0.2) H49D(0.1) H49E(0.1) H49F(0.1)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C10(H10), C20(H20), C45(H45), C35(H35), C28(H28), C23(H23), C48(H48),
 C48(H48A)
4.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C38(H38), C16(H16), C31(H31), C5(H5), C32(H32), C30(H30), C7(H7),
 C6(H6), C18(H18), C17(H17), C43(H43), C41(H41), C42(H42)
4.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C26(H26A,H26B,
 H26C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C46(H46A,H46B,H46C), C27(H27A,
 H27B,H27C), C1(H1A,H1B,H1C), C25(H25A,H25B,H25C), C47(H47A,H47B,H47C),
 C24(H24A,H24B,H24C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C50(H50A,H50B,
 H50C), C49(H49A,H49B,H49C), C50A(H50D,H50E,H50F), C49A(H49D,H49E,H49F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.64625(2) 0.66256(2) 0.73112(2) 0.02328(4) Uani 1 1 d . . . . .
F5 F 0.64650(15) 0.92002(13) 0.65125(8) 0.0344(4) Uani 1 1 d . . . . .
F1 F 0.95027(15) 0.61030(13) 0.77690(8) 0.0347(4) Uani 1 1 d . . . . .
F4 F 0.81064(17) 1.05080(13) 0.62459(9) 0.0417(4) Uani 1 1 d . . . . .
F2 F 1.11668(15) 0.73825(15) 0.74547(9) 0.0406(4) Uani 1 1 d . . . . .
F3 F 1.04878(17) 0.95738(15) 0.66910(9) 0.0429(4) Uani 1 1 d . . . . .
N1 N 0.6788(2) 0.55721(17) 0.83916(10) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.59502(19) 0.75086(17) 0.83453(10) 0.0223(4) Uani 1 1 d . . . . .
N3 N 0.7921(2) 0.52211(18) 0.68226(11) 0.0271(5) Uani 1 1 d . . . . .
N4 N 0.7081(2) 0.68246(18) 0.60386(10) 0.0260(5) Uani 1 1 d . . . . .
C13 C 0.6244(2) 0.6449(2) 0.86994(12) 0.0235(5) Uani 1 1 d . . . . .
H13 H 0.607990 0.629649 0.916171 0.028 Uiso 1 1 calc R U . . .
C14 C 0.5484(2) 0.8478(2) 0.86344(12) 0.0232(5) Uani 1 1 d . . . . .
C34 C 0.8684(3) 0.4026(2) 0.69959(13) 0.0280(5) Uani 1 1 d . . . . .
C52 C 0.9149(3) 0.7173(2) 0.73625(13) 0.0275(5) Uani 1 1 d . . . . .
C51 C 0.7955(2) 0.7592(2) 0.71287(13) 0.0268(5) Uani 1 1 d . . . . .
C38 C 0.7799(2) 0.5755(2) 0.61804(13) 0.0260(5) Uani 1 1 d . . . . .
H38 H 0.821921 0.536454 0.584580 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6652(3) 0.4454(2) 0.87669(12) 0.0259(5) Uani 1 1 d . . . . .
C15 C 0.4163(3) 0.9148(2) 0.86112(13) 0.0278(5) Uani 1 1 d . . . . .
C33 C 0.8043(3) 0.3162(2) 0.72100(13) 0.0313(6) Uani 1 1 d . . . . .
C29 C 1.0049(3) 0.3734(2) 0.69337(13) 0.0313(6) Uani 1 1 d . . . . .
C39 C 0.6814(3) 0.7423(2) 0.53767(12) 0.0271(5) Uani 1 1 d . . . . .
C53 C 1.0011(3) 0.7815(2) 0.72142(14) 0.0312(6) Uani 1 1 d . . . . .
C55 C 0.8458(3) 0.9404(2) 0.66060(14) 0.0319(6) Uani 1 1 d . . . . .
C2 C 0.9118(3) 0.3739(2) 0.87612(13) 0.0323(6) Uani 1 1 d . . . . .
H2 H 0.915609 0.419002 0.829772 0.039 Uiso 1 1 calc R U . . .
C56 C 0.7642(3) 0.8720(2) 0.67531(13) 0.0278(5) Uani 1 1 d . . . . .
C4 C 0.7784(3) 0.3550(2) 0.89595(13) 0.0296(6) Uani 1 1 d . . . . .
C54 C 0.9663(3) 0.8936(2) 0.68298(14) 0.0319(6) Uani 1 1 d . . . . .
C19 C 0.6326(3) 0.8814(2) 0.89012(13) 0.0291(6) Uani 1 1 d . . . . .
C16 C 0.3717(3) 1.0148(2) 0.88498(14) 0.0371(7) Uani 1 1 d . . . . .
H16 H 0.285064 1.060038 0.883235 0.044 Uiso 1 1 calc R U . . .
C31 C 1.0152(3) 0.1711(2) 0.73026(15) 0.0387(7) Uani 1 1 d . . . . .
H31 H 1.064276 0.093260 0.741002 0.046 Uiso 1 1 calc R U . . .
C5 C 0.7620(3) 0.2497(2) 0.93669(14) 0.0361(7) Uani 1 1 d . . . . .
H5 H 0.835151 0.188508 0.949801 0.043 Uiso 1 1 calc R U . . .
C32 C 0.8811(3) 0.2006(2) 0.73636(14) 0.0366(6) Uani 1 1 d . . . . .
H32 H 0.840954 0.141997 0.751061 0.044 Uiso 1 1 calc R U . . .
C30 C 1.0764(3) 0.2557(3) 0.70848(15) 0.0368(6) Uani 1 1 d . . . . .
H30 H 1.167055 0.234649 0.703652 0.044 Uiso 1 1 calc R U . . .
C10 C 0.4163(3) 0.5246(2) 0.87570(13) 0.0294(6) Uani 1 1 d . . . . .
H10 H 0.441691 0.590335 0.844448 0.035 Uiso 1 1 calc R U . . .
C20 C 0.7761(3) 0.8150(3) 0.89073(14) 0.0354(6) Uani 1 1 d . U . . .
H20 H 0.795944 0.755675 0.865501 0.042 Uiso 1 1 calc R U . . .
C45 C 0.9025(3) 0.7822(3) 0.50941(14) 0.0361(6) Uani 1 1 d . . . . .
H45 H 0.909463 0.737158 0.555586 0.043 Uiso 1 1 calc R U . . .
C8 C 0.5408(3) 0.4304(2) 0.89628(12) 0.0287(6) Uani 1 1 d . . . . .
C7 C 0.5306(3) 0.3237(2) 0.93761(13) 0.0347(6) Uani 1 1 d . . . . .
H7 H 0.448833 0.312456 0.951697 0.042 Uiso 1 1 calc R U . . .
C40 C 0.7708(3) 0.7923(2) 0.49210(13) 0.0302(6) Uani 1 1 d . . . . .
C44 C 0.5588(3) 0.7572(2) 0.52044(13) 0.0321(6) Uani 1 1 d . . . . .
C3 C 0.9320(3) 0.4449(3) 0.91907(15) 0.0363(6) Uani 1 1 d . . . . .
H3A H 0.866702 0.519299 0.913266 0.055 Uiso 1 1 calc R U . . .
H3B H 1.016980 0.455658 0.905696 0.055 Uiso 1 1 calc R U . . .
H3C H 0.925101 0.403992 0.965084 0.055 Uiso 1 1 calc R U . . .
C6 C 0.6401(3) 0.2349(2) 0.95776(14) 0.0373(7) Uani 1 1 d . . . . .
H6 H 0.631617 0.164816 0.985645 0.045 Uiso 1 1 calc R U . . .
C35 C 0.6587(3) 0.3448(3) 0.72217(15) 0.0380(7) Uani 1 1 d . . . . .
H35 H 0.616868 0.418786 0.735259 0.046 Uiso 1 1 calc R U . . .
C28 C 1.0787(3) 0.4635(3) 0.66638(15) 0.0374(6) Uani 1 1 d . . . . .
H28 H 1.015784 0.540301 0.666697 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3306(3) 0.5685(3) 0.93511(14) 0.0383(7) Uani 1 1 d . . . . .
H11A H 0.306715 0.505189 0.967474 0.057 Uiso 1 1 calc R U . . .
H11B H 0.253307 0.627997 0.920488 0.057 Uiso 1 1 calc R U . . .
H11C H 0.377815 0.599861 0.954794 0.057 Uiso 1 1 calc R U . . .
C23 C 0.3286(3) 0.8794(2) 0.83026(14) 0.0331(6) Uani 1 1 d . . . . .
H23 H 0.362748 0.795070 0.835235 0.040 Uiso 1 1 calc R U . . .
C18 C 0.5824(3) 0.9817(3) 0.91420(15) 0.0388(7) Uani 1 1 d . . . . .
H18 H 0.636704 1.004304 0.932646 0.047 Uiso 1 1 calc R U . . .
C17 C 0.4542(3) 1.0482(3) 0.91133(16) 0.0435(7) Uani 1 1 d . . . . .
H17 H 0.423057 1.115502 0.927107 0.052 Uiso 1 1 calc R U . . .
C43 C 0.5290(3) 0.8208(3) 0.45717(14) 0.0401(7) Uani 1 1 d . . . . .
H43 H 0.448169 0.831088 0.445257 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3378(3) 0.4849(3) 0.83975(16) 0.0415(7) Uani 1 1 d . . . . .
H12A H 0.390021 0.463958 0.800181 0.062 Uiso 1 1 calc R U . . .
H12B H 0.260471 0.547096 0.827875 0.062 Uiso 1 1 calc R U . . .
H12C H 0.313871 0.418766 0.868696 0.062 Uiso 1 1 calc R U . . .
C41 C 0.7363(3) 0.8546(3) 0.42909(14) 0.0411(7) Uani 1 1 d . . . . .
H41 H 0.795419 0.887166 0.398088 0.049 Uiso 1 1 calc R U . . .
C42 C 0.6167(3) 0.8692(3) 0.41163(16) 0.0468(8) Uani 1 1 d . . . . .
H42 H 0.595334 0.911498 0.369324 0.056 Uiso 1 1 calc R U . . .
C26 C 1.1846(3) 0.4451(3) 0.70936(17) 0.0441(7) Uani 1 1 d . . . . .
H26A H 1.253003 0.374659 0.705535 0.066 Uiso 1 1 calc R U . . .
H26B H 1.147014 0.439548 0.755070 0.066 Uiso 1 1 calc R U . . .
H26C H 1.219714 0.509696 0.694294 0.066 Uiso 1 1 calc R U . . .
C48 C 0.4586(3) 0.7102(3) 0.57088(15) 0.0451(8) Uani 1 1 d . . . . .
H48 H 0.502474 0.639461 0.602051 0.054 Uiso 0.6 1 calc R U P A 1
H48A H 0.497767 0.665998 0.611919 0.054 Uiso 0.4 1 calc R U P B 2
C36 C 0.6008(4) 0.2532(3) 0.77163(17) 0.0498(8) Uani 1 1 d . . . . .
H36A H 0.507370 0.280998 0.774426 0.075 Uiso 1 1 calc R U . . .
H36B H 0.626679 0.238865 0.814747 0.075 Uiso 1 1 calc R U . . .
H36C H 0.632066 0.182334 0.756738 0.075 Uiso 1 1 calc R U . . .
C37 C 0.6244(3) 0.3604(3) 0.65254(17) 0.0471(8) Uani 1 1 d . . . . .
H37A H 0.660811 0.287813 0.639475 0.071 Uiso 1 1 calc R U . . .
H37B H 0.659692 0.418108 0.621159 0.071 Uiso 1 1 calc R U . . .
H37C H 0.531327 0.384950 0.653452 0.071 Uiso 1 1 calc R U . . .
C46 C 0.9129(4) 0.9024(3) 0.50445(17) 0.0542(9) Uani 1 1 d . . . . .
H46A H 0.918298 0.944189 0.458567 0.081 Uiso 1 1 calc R U . . .
H46B H 0.989737 0.894125 0.522590 0.081 Uiso 1 1 calc R U . . .
H46C H 0.837292 0.944528 0.529074 0.081 Uiso 1 1 calc R U . . .
C27 C 1.1393(3) 0.4633(3) 0.59446(17) 0.0495(8) Uani 1 1 d . . . . .
H27A H 1.181331 0.523346 0.577596 0.074 Uiso 1 1 calc R U . . .
H27B H 1.072284 0.477338 0.567669 0.074 Uiso 1 1 calc R U . . .
H27C H 1.202418 0.389173 0.592881 0.074 Uiso 1 1 calc R U . . .
C1 C 1.0243(3) 0.2606(3) 0.88012(16) 0.0447(8) Uani 1 1 d . . . . .
H1A H 1.028449 0.218273 0.925807 0.067 Uiso 1 1 calc R U . . .
H1B H 1.104903 0.278219 0.862014 0.067 Uiso 1 1 calc R U . . .
H1C H 1.010062 0.214150 0.855041 0.067 Uiso 1 1 calc R U . . .
C25 C 0.3345(3) 0.9366(3) 0.75589(15) 0.0439(7) Uani 1 1 d . . . . .
H25A H 0.301968 1.019580 0.749494 0.066 Uiso 1 1 calc R U . . .
H25B H 0.282105 0.910808 0.735931 0.066 Uiso 1 1 calc R U . . .
H25C H 0.423243 0.915354 0.735416 0.066 Uiso 1 1 calc R U . . .
C47 C 1.0160(3) 0.7203(3) 0.46507(17) 0.0480(8) Uani 1 1 d . . . . .
H47A H 1.012433 0.643175 0.469840 0.072 Uiso 1 1 calc R U . . .
H47B H 1.096701 0.716072 0.477902 0.072 Uiso 1 1 calc R U . . .
H47C H 1.010486 0.762780 0.419468 0.072 Uiso 1 1 calc R U . . .
C24 C 0.1879(3) 0.9066(3) 0.86372(17) 0.0490(8) Uani 1 1 d . . . . .
H24A H 0.186793 0.875472 0.910956 0.073 Uiso 1 1 calc R U . . .
H24B H 0.140075 0.871990 0.846569 0.073 Uiso 1 1 calc R U . . .
H24C H 0.148266 0.989294 0.854666 0.073 Uiso 1 1 calc R U . . .
C21 C 0.8092(3) 0.7525(4) 0.96142(18) 0.0608(10) Uani 1 1 d . U . . .
H21A H 0.790232 0.808634 0.987421 0.091 Uiso 1 1 calc R U . . .
H21B H 0.900150 0.709495 0.959859 0.091 Uiso 1 1 calc R U . . .
H21C H 0.757927 0.700009 0.981393 0.091 Uiso 1 1 calc R U . . .
C22 C 0.8593(4) 0.8950(4) 0.8561(2) 0.0624(10) Uani 1 1 d . U . . .
H22A H 0.834001 0.935372 0.812541 0.094 Uiso 1 1 calc R U . . .
H22B H 0.949468 0.849861 0.851986 0.094 Uiso 1 1 calc R U . . .
H22C H 0.847072 0.950348 0.881708 0.094 Uiso 1 1 calc R U . . .
C50 C 0.3560(8) 0.6882(7) 0.5434(4) 0.061(2) Uani 0.6 1 d . . P C 1
H50A H 0.303236 0.760616 0.519289 0.091 Uiso 0.6 1 calc R U P C 1
H50B H 0.301946 0.652961 0.579416 0.091 Uiso 0.6 1 calc R U P C 1
H50C H 0.397184 0.637076 0.514005 0.091 Uiso 0.6 1 calc R U P C 1
C49 C 0.3778(5) 0.8070(5) 0.6096(3) 0.0608(14) Uani 0.8 1 d . U P C 1
H49A H 0.436427 0.832489 0.625488 0.091 Uiso 0.9 1 calc R U P C 1
H49B H 0.322536 0.775824 0.646748 0.091 Uiso 0.9 1 calc R U P C 1
H49C H 0.325113 0.871810 0.580242 0.091 Uiso 0.9 1 calc R U P C 1
C50A C 0.4258(13) 0.6205(13) 0.5382(6) 0.074(4) Uani 0.4 1 d . . P C 2
H50D H 0.376262 0.664248 0.501675 0.112 Uiso 0.4 1 calc R U P C 2
H50E H 0.376159 0.576058 0.571452 0.112 Uiso 0.4 1 calc R U P C 2
H50F H 0.505848 0.568775 0.522465 0.112 Uiso 0.4 1 calc R U P C 2
C49A C 0.3348(19) 0.779(2) 0.5873(11) 0.058(4) Uani 0.2 1 d . U P C 2
H49D H 0.339792 0.835500 0.608063 0.087 Uiso 0.1 1 calc R U P C 2
H49E H 0.285123 0.731058 0.617619 0.087 Uiso 0.1 1 calc R U P C 2
H49F H 0.293024 0.817749 0.547689 0.087 Uiso 0.1 1 calc R U P C 2


_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
Bi1 N1 2.316(2) . ?
Bi1 N2 2.606(2) . ?
Bi1 N3 2.280(2) . ?
Bi1 N4 2.591(2) . ?
Bi1 C51 2.265(3) . ?
F5 C56 1.364(3) . ?
F1 C52 1.348(3) . ?
F4 C55 1.344(3) . ?
F2 C53 1.344(3) . ?
F3 C54 1.340(3) . ?
N1 C13 1.343(3) . ?
N1 C9 1.441(3) . ?
N2 C13 1.293(3) . ?
N2 C14 1.414(3) . ?
N3 C34 1.433(3) . ?
N3 C38 1.341(3) . ?
N4 C38 1.292(3) . ?
N4 C39 1.422(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.413(4) . ?
C14 C19 1.404(4) . ?
C34 C33 1.407(4) . ?
C34 C29 1.404(4) . ?
C52 C51 1.376(4) . ?
C52 C53 1.375(4) . ?
C51 C56 1.376(4) . ?
C38 H38 0.9300 . ?
C9 C4 1.410(4) . ?
C9 C8 1.402(4) . ?
C15 C16 1.387(4) . ?
C15 C23 1.507(4) . ?
C33 C32 1.393(4) . ?
C33 C35 1.512(4) . ?
C29 C30 1.398(4) . ?
C29 C28 1.523(4) . ?
C39 C40 1.399(4) . ?
C39 C44 1.405(4) . ?
C53 C54 1.377(4) . ?
C55 C56 1.375(4) . ?
C55 C54 1.376(4) . ?
C2 H2 0.9800 . ?
C2 C4 1.516(4) . ?
C2 C3 1.536(4) . ?
C2 C1 1.532(4) . ?
C4 C5 1.401(4) . ?
C19 C20 1.514(4) . ?
C19 C18 1.392(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.379(4) . ?
C31 C30 1.367(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(4) . ?
C32 H32 0.9300 . ?
C30 H30 0.9300 . ?
C10 H10 0.9800 . ?
C10 C8 1.521(4) . ?
C10 C11 1.523(4) . ?
C10 C12 1.535(4) . ?
C20 H20 0.9800 . ?
C20 C21 1.528(5) . ?
C20 C22 1.516(4) . ?
C45 H45 0.9800 . ?
C45 C40 1.520(4) . ?
C45 C46 1.528(4) . ?
C45 C47 1.521(4) . ?
C8 C7 1.400(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.380(4) . ?
C40 C41 1.391(4) . ?
C44 C43 1.386(4) . ?
C44 C48 1.510(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C6 H6 0.9300 . ?
C35 H35 0.9800 . ?
C35 C36 1.531(4) . ?
C35 C37 1.536(4) . ?
C28 H28 0.9800 . ?
C28 C26 1.538(4) . ?
C28 C27 1.527(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C23 H23 0.9800 . ?
C23 C25 1.525(4) . ?
C23 C24 1.526(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.376(5) . ?
C17 H17 0.9300 . ?
C43 H43 0.9300 . ?
C43 C42 1.377(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C41 H41 0.9300 . ?
C41 C42 1.376(5) . ?
C42 H42 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C48 H48 0.9800 . ?
C48 H48A 0.9800 . ?
C48 C50 1.504(8) . ?
C48 C49 1.576(6) . ?
C48 C50A 1.647(14) . ?
C48 C49A 1.38(2) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50A H50D 0.9600 . ?
C50A H50E 0.9600 . ?
C50A H50F 0.9600 . ?
C49A H49D 0.9600 . ?
C49A H49E 0.9600 . ?
C49A H49F 0.9600 . ?

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
N1 Bi1 N2 54.64(7) . . ?
N1 Bi1 N4 149.70(7) . . ?
N3 Bi1 N1 95.01(8) . . ?
N3 Bi1 N2 143.49(7) . . ?
N3 Bi1 N4 54.82(8) . . ?
N4 Bi1 N2 150.03(7) . . ?
C51 Bi1 N1 98.67(9) . . ?
C51 Bi1 N2 76.17(8) . . ?
C51 Bi1 N3 91.07(9) . . ?
C51 Bi1 N4 80.96(8) . . ?
C13 N1 Bi1 98.39(15) . . ?
C13 N1 C9 116.0(2) . . ?
C9 N1 Bi1 132.90(16) . . ?
C13 N2 Bi1 86.69(15) . . ?
C13 N2 C14 122.4(2) . . ?
C14 N2 Bi1 150.71(15) . . ?
C34 N3 Bi1 140.11(17) . . ?
C38 N3 Bi1 99.65(16) . . ?
C38 N3 C34 119.5(2) . . ?
C38 N4 Bi1 86.89(16) . . ?
C38 N4 C39 121.8(2) . . ?
C39 N4 Bi1 149.57(17) . . ?
N1 C13 H13 120.4 . . ?
N2 C13 N1 119.2(2) . . ?
N2 C13 H13 120.4 . . ?
C15 C14 N2 118.3(2) . . ?
C19 C14 N2 121.2(2) . . ?
C19 C14 C15 120.4(2) . . ?
C33 C34 N3 118.9(2) . . ?
C29 C34 N3 119.8(2) . . ?
C29 C34 C33 121.3(2) . . ?
F1 C52 C51 120.0(2) . . ?
F1 C52 C53 117.2(2) . . ?
C53 C52 C51 122.8(2) . . ?
C52 C51 Bi1 126.68(19) . . ?
C56 C51 Bi1 117.36(19) . . ?
C56 C51 C52 116.0(2) . . ?
N3 C38 H38 120.9 . . ?
N4 C38 N3 118.3(2) . . ?
N4 C38 H38 120.9 . . ?
C4 C9 N1 118.5(2) . . ?
C8 C9 N1 119.9(2) . . ?
C8 C9 C4 121.6(2) . . ?
C14 C15 C23 119.6(2) . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 C23 121.5(2) . . ?
C34 C33 C35 122.2(2) . . ?
C32 C33 C34 117.6(3) . . ?
C32 C33 C35 120.0(3) . . ?
C34 C29 C28 123.0(2) . . ?
C30 C29 C34 118.2(3) . . ?
C30 C29 C28 118.6(3) . . ?
C40 C39 N4 121.1(2) . . ?
C40 C39 C44 120.6(2) . . ?
C44 C39 N4 118.2(2) . . ?
F2 C53 C52 121.3(2) . . ?
F2 C53 C54 119.4(2) . . ?
C52 C53 C54 119.3(2) . . ?
F4 C55 C56 121.4(2) . . ?
F4 C55 C54 119.7(2) . . ?
C56 C55 C54 118.9(2) . . ?
C4 C2 H2 107.7 . . ?
C4 C2 C3 110.9(2) . . ?
C4 C2 C1 113.5(2) . . ?
C3 C2 H2 107.7 . . ?
C1 C2 H2 107.7 . . ?
C1 C2 C3 109.1(2) . . ?
F5 C56 C51 119.2(2) . . ?
F5 C56 C55 117.5(2) . . ?
C55 C56 C51 123.3(2) . . ?
C9 C4 C2 120.9(2) . . ?
C5 C4 C9 117.5(3) . . ?
C5 C4 C2 121.5(2) . . ?
F3 C54 C53 119.7(2) . . ?
F3 C54 C55 120.5(2) . . ?
C55 C54 C53 119.8(2) . . ?
C14 C19 C20 122.1(2) . . ?
C18 C19 C14 118.4(3) . . ?
C18 C19 C20 119.5(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.6 . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.3 . . ?
C33 C32 H32 119.2 . . ?
C31 C32 C33 121.5(3) . . ?
C31 C32 H32 119.2 . . ?
C29 C30 H30 119.5 . . ?
C31 C30 C29 121.0(3) . . ?
C31 C30 H30 119.5 . . ?
C8 C10 H10 107.5 . . ?
C8 C10 C11 111.5(2) . . ?
C8 C10 C12 112.7(2) . . ?
C11 C10 H10 107.5 . . ?
C11 C10 C12 110.0(2) . . ?
C12 C10 H10 107.5 . . ?
C19 C20 H20 107.7 . . ?
C19 C20 C21 111.7(2) . . ?
C19 C20 C22 110.7(3) . . ?
C21 C20 H20 107.7 . . ?
C22 C20 H20 107.7 . . ?
C22 C20 C21 111.3(3) . . ?
C40 C45 H45 108.2 . . ?
C40 C45 C46 110.5(3) . . ?
C40 C45 C47 112.6(2) . . ?
C46 C45 H45 108.2 . . ?
C47 C45 H45 108.2 . . ?
C47 C45 C46 109.2(3) . . ?
C9 C8 C10 123.4(2) . . ?
C7 C8 C9 118.2(3) . . ?
C7 C8 C10 118.4(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 H7 119.5 . . ?
C39 C40 C45 122.4(2) . . ?
C41 C40 C39 118.4(3) . . ?
C41 C40 C45 119.2(3) . . ?
C39 C44 C48 120.8(2) . . ?
C43 C44 C39 118.7(3) . . ?
C43 C44 C48 120.5(3) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C33 C35 H35 107.9 . . ?
C33 C35 C36 113.5(3) . . ?
C33 C35 C37 110.7(3) . . ?
C36 C35 H35 107.9 . . ?
C36 C35 C37 108.8(3) . . ?
C37 C35 H35 107.9 . . ?
C29 C28 H28 107.8 . . ?
C29 C28 C26 112.5(3) . . ?
C29 C28 C27 110.7(2) . . ?
C26 C28 H28 107.8 . . ?
C27 C28 H28 107.8 . . ?
C27 C28 C26 110.0(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C23 H23 107.6 . . ?
C15 C23 C25 109.6(2) . . ?
C15 C23 C24 113.3(3) . . ?
C25 C23 H23 107.6 . . ?
C25 C23 C24 110.8(2) . . ?
C24 C23 H23 107.6 . . ?
C19 C18 H18 119.3 . . ?
C17 C18 C19 121.5(3) . . ?
C17 C18 H18 119.3 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C44 C43 H43 119.4 . . ?
C42 C43 C44 121.3(3) . . ?
C42 C43 H43 119.4 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C40 C41 H41 119.3 . . ?
C42 C41 C40 121.5(3) . . ?
C42 C41 H41 119.3 . . ?
C43 C42 H42 120.2 . . ?
C41 C42 C43 119.6(3) . . ?
C41 C42 H42 120.2 . . ?
C28 C26 H26A 109.5 . . ?
C28 C26 H26B 109.5 . . ?
C28 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C44 C48 H48 109.9 . . ?
C44 C48 H48A 108.9 . . ?
C44 C48 C49 107.2(3) . . ?
C44 C48 C50A 105.6(5) . . ?
C50 C48 C44 116.4(4) . . ?
C50 C48 H48 109.9 . . ?
C50 C48 C49 103.4(4) . . ?
C49 C48 H48 109.9 . . ?
C50A C48 H48A 108.9 . . ?
C49A C48 C44 122.9(9) . . ?
C49A C48 H48A 108.9 . . ?
C49A C48 C50A 100.8(11) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
C28 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C48 C50 H50A 109.5 . . ?
C48 C50 H50B 109.5 . . ?
C48 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C48 C50A H50D 109.5 . . ?
C48 C50A H50E 109.5 . . ?
C48 C50A H50F 109.5 . . ?
H50D C50A H50E 109.5 . . ?
H50D C50A H50F 109.5 . . ?
H50E C50A H50F 109.5 . . ?
C48 C49A H49D 109.5 . . ?
C48 C49A H49E 109.5 . . ?
C48 C49A H49F 109.5 . . ?
H49D C49A H49E 109.5 . . ?
H49D C49A H49F 109.5 . . ?
H49E C49A H49F 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
Bi1 N1 C13 N2 -11.0(2) . . . . ?
Bi1 N1 C9 C4 113.6(2) . . . . ?
Bi1 N1 C9 C8 -70.0(3) . . . . ?
Bi1 N2 C13 N1 9.7(2) . . . . ?
Bi1 N2 C14 C15 62.9(4) . . . . ?
Bi1 N2 C14 C19 -113.1(3) . . . . ?
Bi1 N3 C34 C33 69.4(3) . . . . ?
Bi1 N3 C34 C29 -112.2(3) . . . . ?
Bi1 N3 C38 N4 6.4(3) . . . . ?
Bi1 N4 C38 N3 -5.5(2) . . . . ?
Bi1 N4 C39 C40 119.7(3) . . . . ?
Bi1 N4 C39 C44 -56.0(4) . . . . ?
Bi1 C51 C56 F5 0.2(3) . . . . ?
Bi1 C51 C56 C55 179.9(2) . . . . ?
F1 C52 C51 Bi1 -3.3(4) . . . . ?
F1 C52 C51 C56 175.9(2) . . . . ?
F1 C52 C53 F2 1.3(4) . . . . ?
F1 C52 C53 C54 -176.6(2) . . . . ?
F4 C55 C56 F5 0.8(4) . . . . ?
F4 C55 C56 C51 -178.9(2) . . . . ?
F4 C55 C54 F3 0.0(4) . . . . ?
F4 C55 C54 C53 178.2(2) . . . . ?
F2 C53 C54 F3 1.1(4) . . . . ?
F2 C53 C54 C55 -177.2(2) . . . . ?
N1 C9 C4 C2 -1.6(4) . . . . ?
N1 C9 C4 C5 175.2(2) . . . . ?
N1 C9 C8 C10 4.7(4) . . . . ?
N1 C9 C8 C7 -174.4(2) . . . . ?
N2 C14 C15 C16 -175.4(2) . . . . ?
N2 C14 C15 C23 1.9(3) . . . . ?
N2 C14 C19 C20 -1.3(4) . . . . ?
N2 C14 C19 C18 176.1(2) . . . . ?
N3 C34 C33 C32 178.8(2) . . . . ?
N3 C34 C33 C35 4.0(4) . . . . ?
N3 C34 C29 C30 -177.8(2) . . . . ?
N3 C34 C29 C28 -2.2(4) . . . . ?
N4 C39 C40 C45 2.2(4) . . . . ?
N4 C39 C40 C41 -176.9(3) . . . . ?
N4 C39 C44 C43 176.5(3) . . . . ?
N4 C39 C44 C48 -0.3(4) . . . . ?
C13 N1 C9 C4 -113.9(3) . . . . ?
C13 N1 C9 C8 62.6(3) . . . . ?
C13 N2 C14 C15 -109.2(3) . . . . ?
C13 N2 C14 C19 74.8(3) . . . . ?
C14 N2 C13 N1 -174.2(2) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C14 C15 C23 C25 -89.3(3) . . . . ?
C14 C15 C23 C24 146.4(3) . . . . ?
C14 C19 C20 C21 -111.4(3) . . . . ?
C14 C19 C20 C22 124.0(3) . . . . ?
C14 C19 C18 C17 -1.0(4) . . . . ?
C34 N3 C38 N4 178.4(2) . . . . ?
C34 C33 C32 C31 -0.7(4) . . . . ?
C34 C33 C35 C36 -156.1(3) . . . . ?
C34 C33 C35 C37 81.2(3) . . . . ?
C34 C29 C30 C31 -1.5(4) . . . . ?
C34 C29 C28 C26 133.9(3) . . . . ?
C34 C29 C28 C27 -102.6(3) . . . . ?
C52 C51 C56 F5 -179.1(2) . . . . ?
C52 C51 C56 C55 0.7(4) . . . . ?
C52 C53 C54 F3 179.0(2) . . . . ?
C52 C53 C54 C55 0.7(4) . . . . ?
C51 C52 C53 F2 179.5(2) . . . . ?
C51 C52 C53 C54 1.7(4) . . . . ?
C38 N3 C34 C33 -98.3(3) . . . . ?
C38 N3 C34 C29 80.0(3) . . . . ?
C38 N4 C39 C40 -82.0(3) . . . . ?
C38 N4 C39 C44 102.4(3) . . . . ?
C9 N1 C13 N2 -157.9(2) . . . . ?
C9 C4 C5 C6 -0.5(4) . . . . ?
C9 C8 C7 C6 -0.9(4) . . . . ?
C15 C14 C19 C20 -177.2(2) . . . . ?
C15 C14 C19 C18 0.2(4) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C33 C34 C29 C30 0.6(4) . . . . ?
C33 C34 C29 C28 176.1(3) . . . . ?
C29 C34 C33 C32 0.5(4) . . . . ?
C29 C34 C33 C35 -174.4(3) . . . . ?
C39 N4 C38 N3 -174.8(2) . . . . ?
C39 C40 C41 C42 1.0(5) . . . . ?
C39 C44 C43 C42 -0.1(5) . . . . ?
C39 C44 C48 C50 -157.1(5) . . . . ?
C39 C44 C48 C49 87.8(4) . . . . ?
C39 C44 C48 C50A -121.6(6) . . . . ?
C39 C44 C48 C49A 124.0(13) . . . . ?
C53 C52 C51 Bi1 178.5(2) . . . . ?
C53 C52 C51 C56 -2.4(4) . . . . ?
C2 C4 C5 C6 176.3(2) . . . . ?
C56 C55 C54 F3 179.4(2) . . . . ?
C56 C55 C54 C53 -2.3(4) . . . . ?
C4 C9 C8 C10 -178.9(2) . . . . ?
C4 C9 C8 C7 1.9(4) . . . . ?
C4 C5 C6 C7 1.5(4) . . . . ?
C54 C55 C56 F5 -178.7(2) . . . . ?
C54 C55 C56 C51 1.6(4) . . . . ?
C19 C14 C15 C16 0.7(4) . . . . ?
C19 C14 C15 C23 178.0(2) . . . . ?
C19 C18 C17 C16 1.0(5) . . . . ?
C16 C15 C23 C25 88.0(3) . . . . ?
C16 C15 C23 C24 -36.3(4) . . . . ?
C32 C33 C35 C36 29.1(4) . . . . ?
C32 C33 C35 C37 -93.5(3) . . . . ?
C32 C31 C30 C29 1.4(4) . . . . ?
C30 C29 C28 C26 -50.5(4) . . . . ?
C30 C29 C28 C27 73.0(3) . . . . ?
C30 C31 C32 C33 -0.3(5) . . . . ?
C10 C8 C7 C6 179.8(2) . . . . ?
C20 C19 C18 C17 176.5(3) . . . . ?
C45 C40 C41 C42 -178.1(3) . . . . ?
C8 C9 C4 C2 -178.1(2) . . . . ?
C8 C9 C4 C5 -1.2(4) . . . . ?
C8 C7 C6 C5 -0.7(4) . . . . ?
C40 C39 C44 C43 0.8(4) . . . . ?
C40 C39 C44 C48 -176.0(3) . . . . ?
C40 C41 C42 C43 -0.3(5) . . . . ?
C44 C39 C40 C45 177.7(3) . . . . ?
C44 C39 C40 C41 -1.3(4) . . . . ?
C44 C43 C42 C41 -0.2(5) . . . . ?
C3 C2 C4 C9 76.2(3) . . . . ?
C3 C2 C4 C5 -100.5(3) . . . . ?
C35 C33 C32 C31 174.3(3) . . . . ?
C28 C29 C30 C31 -177.3(3) . . . . ?
C11 C10 C8 C9 -112.4(3) . . . . ?
C11 C10 C8 C7 66.8(3) . . . . ?
C23 C15 C16 C17 -178.0(3) . . . . ?
C18 C19 C20 C21 71.2(4) . . . . ?
C18 C19 C20 C22 -53.4(4) . . . . ?
C43 C44 C48 C50 26.1(6) . . . . ?
C43 C44 C48 C49 -88.9(4) . . . . ?
C43 C44 C48 C50A 61.6(6) . . . . ?
C43 C44 C48 C49A -52.7(13) . . . . ?
C12 C10 C8 C9 123.3(3) . . . . ?
C12 C10 C8 C7 -57.5(3) . . . . ?
C48 C44 C43 C42 176.8(3) . . . . ?
C46 C45 C40 C39 -118.4(3) . . . . ?
C46 C45 C40 C41 60.6(4) . . . . ?
C1 C2 C4 C9 -160.6(2) . . . . ?
C1 C2 C4 C5 22.7(4) . . . . ?
C47 C45 C40 C39 119.2(3) . . . . ?
C47 C45 C40 C41 -61.7(4) . . . . ?

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

data_p21n
_database_code_depnum_ccdc_archive 'CCDC 2243053'
loop_
_audit_author_name
_audit_author_address
'Peter Junk'
;James Cook University
Australia
;
_audit_update_record             
;
2023-02-19 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_audit_creation_date             2021-08-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H36 F4 N2, 0.5(C4 H8 O)'
_chemical_formula_sum            'C33 H40 F4 N2 O0.50'
_chemical_formula_weight         548.67
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.020(2)
_cell_length_b                   19.180(4)
_cell_length_c                   14.340(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.09(3)
_cell_angle_gamma                90
_cell_volume                     3007.8(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5111
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            69721
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         1.782
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4552
_reflns_number_total             5111
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         5111
_refine_ls_number_restraints     81
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0783P)²+1.1176P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1285
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: O1(0.5) C32(0.5) H32A(0.5) H32B(0.5) C33(0.5) H33A(0.5) H33B(0.5)
 C34(0.5) H34A(0.5) H34B(0.5) C35(0.5) H35A(0.5) H35B(0.5)
 Fixed Uiso: H13(0.033) H16(0.04) H7(0.042) H6(0.043) H20(0.04) H23(0.039)
 H18(0.042) H3(0.04) H29(0.044) H5(0.04) H17(0.044) H10(0.043) H2A(0.063)
 H2B(0.063) H2C(0.063) H1A(0.063) H1B(0.063) H1C(0.063) H24A(0.065) H24B(0.065)
 H24C(0.065) H25A(0.07) H25B(0.07) H25C(0.07) H22A(0.074) H22B(0.074)
 H22C(0.074) H11A(0.085) H11B(0.085) H11C(0.085) H21A(0.084) H21B(0.084)
 H21C(0.084) H12A(0.085) H12B(0.085) H12C(0.085) H32A(0.174) H32B(0.174)
 H33A(0.16) H33B(0.16) H34A(0.127) H34B(0.127) H35A(0.154) H35B(0.154)
 Fixed X: H13(0.664592) H16(1.100865) H7(0.230715) H6(0.175648) H20(0.801726)
 H23(0.743703) H18(1.052616) H3(0.522796) H29(0.395641) H5(0.287171)
 H17(1.176603) H10(0.483648) H2A(0.336072) H2B(0.43227) H2C(0.329094)
 H1A(0.61162) H1B(0.600885) H1C(0.505287) H24A(0.968624) H24B(0.83816)
 H24C(0.900774) H25A(0.75819) H25B(0.7612) H25C(0.885092) H22A(0.990338)
 H22B(0.925412) H22C(1.038562) H11A(0.381474) H11B(0.487914) H11C(0.513287)
 H21A(0.913781) H21B(0.809157) H21C(0.779113) H12A(0.287573) H12B(0.347029)
 H12C(0.242964) H32A(0.45079) H32B(0.371515) H33A(0.381354) H33B(0.307185)
 H34A(0.506856) H34B(0.509058) H35A(0.612477) H35B(0.679909)
 Fixed Y: H13(0.707194) H16(0.823048) H7(0.584523) H6(0.671818) H20(0.847365)
 H23(0.607515) H18(0.621381) H3(0.827433) H29(0.740779) H5(0.774544)
 H17(0.719381) H10(0.594122) H2A(0.88478) H2B(0.929167) H2C(0.884501)
 H1A(0.783851) H1B(0.86694) H1C(0.818798) H24A(0.531351) H24B(0.501191)
 H24C(0.562118) H25A(0.601841) H25B(0.524264) H25C(0.560612) H22A(0.863764)
 H22B(0.936396) H22C(0.910114) H11A(0.495761) H11B(0.479773) H11C(0.530743)
 H21A(0.913383) H21B(0.948515) H21C(0.880747) H12A(0.596761) H12B(0.52066)
 H12C(0.536554) H32A(1.035445) H32B(0.966431) H33A(0.999713) H33B(1.056205)
 H34A(1.08022) H34B(1.10982) H35A(1.015277) H35B(1.038457)
 Fixed Z: H13(0.295793) H16(0.405409) H7(0.213401) H6(0.103858) H20(0.473153)
 H23(0.384702) H18(0.33257) H3(0.288856) H29(0.706838) H5(0.106908)
 H17(0.350991) H10(0.398432) H2A(0.153775) H2B(0.222459) H2C(0.264585)
 H1A(0.158793) H1B(0.151709) H1C(0.087935) H24A(0.41225) H24B(0.430348)
 H24C(0.495728) H25A(0.223615) H25B(0.264924) H25C(0.242549) H22A(0.570911)
 H22B(0.540982) H22C(0.490286) H11A(0.260968) H11B(0.344598) H11C(0.260792)
 H21A(0.326744) H21B(0.379118) H21C(0.315329) H12A(0.449838) H12B(0.46163)
 H12C(0.376239) H32A(0.367033) H32B(0.378358) H33A(0.54086) H33B(0.467596)
 H34A(0.408458) H34B(0.513295) H35A(0.574035) H35B(0.484334)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F4 F 0.62747(8) 0.63316(5) 0.52652(6) 0.0334(2) Uani 1 1 d . . . . .
F1 F 0.34950(8) 0.81139(5) 0.41443(6) 0.0358(2) Uani 1 1 d . . . . .
F3 F 0.56596(9) 0.65053(5) 0.69766(6) 0.0413(3) Uani 1 1 d . . . . .
F2 F 0.27643(9) 0.82051(6) 0.58393(7) 0.0461(3) Uani 1 1 d . . . . .
N1 N 0.52409(11) 0.71463(7) 0.37196(8) 0.0275(3) Uani 1 1 d . . . . .
N2 N 0.72962(11) 0.73601(7) 0.41975(9) 0.0276(3) Uani 1 1 d . . . . .
C13 C 0.64429(13) 0.71834(8) 0.35653(10) 0.0273(3) Uani 1 1 d . . . . .
H13 H 0.664592 0.707194 0.295793 0.033 Uiso 1 1 calc R U . . .
C26 C 0.49119(14) 0.72223(8) 0.46390(10) 0.0286(3) Uani 1 1 d . . . . .
C14 C 0.85187(14) 0.72971(8) 0.39918(10) 0.0277(3) Uani 1 1 d . . . . .
C9 C 0.42952(13) 0.70213(8) 0.29436(10) 0.0283(3) Uani 1 1 d . . . . .
C15 C 0.92813(14) 0.78889(8) 0.41379(10) 0.0297(3) Uani 1 1 d . . . . .
C31 C 0.54354(14) 0.68197(8) 0.53921(11) 0.0297(3) Uani 1 1 d . . . . .
C19 C 0.89837(14) 0.66556(8) 0.37103(10) 0.0300(3) Uani 1 1 d . . . . .
C4 C 0.40127(14) 0.75446(8) 0.22646(10) 0.0296(3) Uani 1 1 d . . . . .
C27 C 0.40174(14) 0.76935(9) 0.48301(11) 0.0314(3) Uani 1 1 d . . . . .
C16 C 1.04875(15) 0.78357(9) 0.39593(11) 0.0334(4) Uani 1 1 d . . . . .
H16 H 1.100865 0.823048 0.405409 0.040 Uiso 1 1 calc R U . . .
C8 C 0.37022(14) 0.63711(8) 0.28921(11) 0.0310(3) Uani 1 1 d . . . . .
C7 C 0.27454(15) 0.62729(9) 0.21728(11) 0.0347(4) Uani 1 1 d . . . . .
H7 H 0.230715 0.584523 0.213401 0.042 Uiso 1 1 calc R U . . .
C6 C 0.24246(15) 0.67890(9) 0.15146(11) 0.0356(4) Uani 1 1 d . . . . .
H6 H 0.175648 0.671818 0.103858 0.043 Uiso 1 1 calc R U . . .
C30 C 0.50949(15) 0.68998(9) 0.62815(11) 0.0333(4) Uani 1 1 d . . . . .
C20 C 0.87781(15) 0.85777(8) 0.44428(11) 0.0335(4) Uani 1 1 d . . . . .
H20 H 0.801726 0.847365 0.473153 0.040 Uiso 1 1 calc R U . . .
C23 C 0.82576(15) 0.59763(8) 0.36469(11) 0.0328(3) Uani 1 1 d . . . . .
H23 H 0.743703 0.607515 0.384702 0.039 Uiso 1 1 calc R U . . .
C18 C 1.02010(15) 0.66376(9) 0.35316(11) 0.0349(4) Uani 1 1 d . . . . .
H18 H 1.052616 0.621381 0.332570 0.042 Uiso 1 1 calc R U . . .
C3 C 0.47047(15) 0.82315(9) 0.22700(11) 0.0337(4) Uani 1 1 d . . . . .
H3 H 0.522796 0.827433 0.288856 0.040 Uiso 1 1 calc R U . . .
C29 C 0.41950(15) 0.73596(9) 0.64573(11) 0.0367(4) Uani 1 1 d . . . . .
H29 H 0.395641 0.740779 0.706838 0.044 Uiso 1 1 calc R U . . .
C5 C 0.30722(14) 0.74069(9) 0.15469(11) 0.0337(4) Uani 1 1 d . . . . .
H5 H 0.287171 0.774544 0.106908 0.040 Uiso 1 1 calc R U . . .
C28 C 0.36547(15) 0.77462(9) 0.57153(11) 0.0356(4) Uani 1 1 d . . . . .
C17 C 1.09449(15) 0.72181(9) 0.36458(11) 0.0363(4) Uani 1 1 d . . . . .
H17 H 1.176603 0.719381 0.350991 0.044 Uiso 1 1 calc R U . . .
C10 C 0.41105(15) 0.57758(9) 0.35537(12) 0.0358(4) Uani 1 1 d . . . . .
H10 H 0.483648 0.594122 0.398432 0.043 Uiso 1 1 calc R U . . .
C2 C 0.38420(17) 0.88607(9) 0.21596(13) 0.0423(4) Uani 1 1 d . . . . .
H2A H 0.336072 0.884780 0.153775 0.063 Uiso 1 1 calc R U . . .
H2B H 0.432270 0.929167 0.222459 0.063 Uiso 1 1 calc R U . . .
H2C H 0.329094 0.884501 0.264585 0.063 Uiso 1 1 calc R U . . .
C1 C 0.55468(17) 0.82319(10) 0.14934(12) 0.0422(4) Uani 1 1 d . . . . .
H1A H 0.611620 0.783851 0.158793 0.063 Uiso 1 1 calc R U . . .
H1B H 0.600885 0.866940 0.151709 0.063 Uiso 1 1 calc R U . . .
H1C H 0.505287 0.818798 0.087935 0.063 Uiso 1 1 calc R U . . .
C24 C 0.88900(17) 0.54319(10) 0.43177(13) 0.0432(4) Uani 1 1 d . . . . .
H24A H 0.968624 0.531351 0.412250 0.065 Uiso 1 1 calc R U . . .
H24B H 0.838160 0.501191 0.430348 0.065 Uiso 1 1 calc R U . . .
H24C H 0.900774 0.562118 0.495728 0.065 Uiso 1 1 calc R U . . .
C25 C 0.80578(19) 0.56848(10) 0.26504(12) 0.0465(4) Uani 1 1 d . . . . .
H25A H 0.758190 0.601841 0.223615 0.070 Uiso 1 1 calc R U . . .
H25B H 0.761200 0.524264 0.264924 0.070 Uiso 1 1 calc R U . . .
H25C H 0.885092 0.560612 0.242549 0.070 Uiso 1 1 calc R U . . .
C22 C 0.96593(18) 0.89538(10) 0.51824(15) 0.0494(5) Uani 1 1 d . . . . .
H22A H 0.990338 0.863764 0.570911 0.074 Uiso 1 1 calc R U . . .
H22B H 0.925412 0.936396 0.540982 0.074 Uiso 1 1 calc R U . . .
H22C H 1.038562 0.910114 0.490286 0.074 Uiso 1 1 calc R U . . .
C11 C 0.4521(2) 0.51539(11) 0.30052(16) 0.0564(5) Uani 1 1 d . . . . .
H11A H 0.381474 0.495761 0.260968 0.085 Uiso 1 1 calc R U . . .
H11B H 0.487914 0.479773 0.344598 0.085 Uiso 1 1 calc R U . . .
H11C H 0.513287 0.530743 0.260792 0.085 Uiso 1 1 calc R U . . .
C21 C 0.8417(2) 0.90428(11) 0.35868(14) 0.0562(5) Uani 1 1 d . . . . .
H21A H 0.913781 0.913383 0.326744 0.084 Uiso 1 1 calc R U . . .
H21B H 0.809157 0.948515 0.379118 0.084 Uiso 1 1 calc R U . . .
H21C H 0.779113 0.880747 0.315329 0.084 Uiso 1 1 calc R U . . .
C12 C 0.31345(19) 0.55596(12) 0.41619(16) 0.0568(5) Uani 1 1 d . . . . .
H12A H 0.287573 0.596761 0.449838 0.085 Uiso 1 1 calc R U . . .
H12B H 0.347029 0.520660 0.461630 0.085 Uiso 1 1 calc R U . . .
H12C H 0.242964 0.536554 0.376239 0.085 Uiso 1 1 calc R U . . .
O1 O 0.5473(6) 0.9600(4) 0.4506(6) 0.157(3) Uani 0.5 1 d D U P A -1
C32 C 0.4312(8) 0.9992(6) 0.4119(7) 0.145(3) Uani 0.5 1 d D U P A -1
H32A H 0.450790 1.035445 0.367033 0.174 Uiso 0.5 1 calc R U P A -1
H32B H 0.371515 0.966431 0.378358 0.174 Uiso 0.5 1 calc R U P A -1
C33 C 0.3830(8) 1.0289(6) 0.4840(7) 0.133(3) Uani 0.5 1 d D U P A -1
H33A H 0.381354 0.999713 0.540860 0.160 Uiso 0.5 1 calc R U P A -1
H33B H 0.307185 1.056205 0.467596 0.160 Uiso 0.5 1 calc R U P A -1
C34 C 0.5038(6) 1.0668(4) 0.4748(7) 0.106(2) Uani 0.5 1 d D U P A -1
H34A H 0.506856 1.080220 0.408458 0.127 Uiso 0.5 1 calc R U P A -1
H34B H 0.509058 1.109820 0.513295 0.127 Uiso 0.5 1 calc R U P A -1
C35 C 0.6020(8) 1.0228(5) 0.5052(7) 0.128(3) Uani 0.5 1 d D U P A -1
H35A H 0.612477 1.015277 0.574035 0.154 Uiso 0.5 1 calc R U P A -1
H35B H 0.679909 1.038457 0.484334 0.154 Uiso 0.5 1 calc R U P A -1


_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
F4 C31 1.3442(18) . ?
F1 C27 1.3449(19) . ?
F3 C30 1.3419(19) . ?
F2 C28 1.3462(19) . ?
N1 C13 1.3715(19) . ?
N1 C26 1.4174(19) . ?
N1 C9 1.448(2) . ?
N2 C13 1.269(2) . ?
N2 C14 1.4194(19) . ?
C13 H13 0.9500 . ?
C26 C31 1.393(2) . ?
C26 C27 1.389(2) . ?
C14 C15 1.413(2) . ?
C14 C19 1.411(2) . ?
C9 C4 1.406(2) . ?
C9 C8 1.406(2) . ?
C15 C16 1.388(2) . ?
C15 C20 1.518(2) . ?
C31 C30 1.382(2) . ?
C19 C23 1.526(2) . ?
C19 C18 1.397(2) . ?
C4 C3 1.522(2) . ?
C4 C5 1.393(2) . ?
C27 C28 1.381(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(2) . ?
C8 C7 1.394(2) . ?
C8 C10 1.517(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.381(2) . ?
C30 C29 1.373(2) . ?
C20 H20 1.0000 . ?
C20 C22 1.528(3) . ?
C20 C21 1.530(2) . ?
C23 H23 1.0000 . ?
C23 C24 1.528(2) . ?
C23 C25 1.525(2) . ?
C18 H18 0.9500 . ?
C18 C17 1.380(2) . ?
C3 H3 1.0000 . ?
C3 C2 1.532(2) . ?
C3 C1 1.535(2) . ?
C29 H29 0.9500 . ?
C29 C28 1.371(2) . ?
C5 H5 0.9500 . ?
C17 H17 0.9500 . ?
C10 H10 1.0000 . ?
C10 C11 1.528(3) . ?
C10 C12 1.523(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O1 C32 1.528(9) . ?
O1 C35 1.520(9) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.346(10) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.537(10) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.400(9) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C26 120.51(12) . . ?
C13 N1 C9 120.17(12) . . ?
C26 N1 C9 119.31(12) . . ?
C13 N2 C14 117.87(13) . . ?
N1 C13 H13 118.5 . . ?
N2 C13 N1 122.95(13) . . ?
N2 C13 H13 118.5 . . ?
C31 C26 N1 122.34(14) . . ?
C27 C26 N1 121.30(14) . . ?
C27 C26 C31 116.34(14) . . ?
C15 C14 N2 117.60(13) . . ?
C19 C14 N2 121.42(14) . . ?
C19 C14 C15 120.85(14) . . ?
C4 C9 N1 119.40(14) . . ?
C8 C9 N1 118.25(14) . . ?
C8 C9 C4 122.35(15) . . ?
C14 C15 C20 120.69(14) . . ?
C16 C15 C14 118.63(14) . . ?
C16 C15 C20 120.63(14) . . ?
F4 C31 C26 120.47(13) . . ?
F4 C31 C30 118.18(14) . . ?
C30 C31 C26 121.34(15) . . ?
C14 C19 C23 123.74(14) . . ?
C18 C19 C14 117.71(15) . . ?
C18 C19 C23 118.45(14) . . ?
C9 C4 C3 123.12(14) . . ?
C5 C4 C9 117.22(15) . . ?
C5 C4 C3 119.64(14) . . ?
F1 C27 C26 119.73(13) . . ?
F1 C27 C28 118.81(14) . . ?
C28 C27 C26 121.46(15) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.23(15) . . ?
C17 C16 H16 119.4 . . ?
C9 C8 C10 122.33(15) . . ?
C7 C8 C9 117.59(15) . . ?
C7 C8 C10 120.00(15) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 120.97(16) . . ?
C6 C7 H7 119.5 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.24(16) . . ?
C5 C6 H6 119.9 . . ?
F3 C30 C31 117.98(15) . . ?
F3 C30 C29 120.33(14) . . ?
C29 C30 C31 121.69(15) . . ?
C15 C20 H20 107.5 . . ?
C15 C20 C22 112.79(14) . . ?
C15 C20 C21 110.15(14) . . ?
C22 C20 H20 107.5 . . ?
C22 C20 C21 111.21(16) . . ?
C21 C20 H20 107.5 . . ?
C19 C23 H23 107.9 . . ?
C19 C23 C24 110.54(14) . . ?
C24 C23 H23 107.9 . . ?
C25 C23 C19 112.52(14) . . ?
C25 C23 H23 107.9 . . ?
C25 C23 C24 109.95(15) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 C19 121.88(15) . . ?
C17 C18 H18 119.1 . . ?
C4 C3 H3 108.0 . . ?
C4 C3 C2 112.16(14) . . ?
C4 C3 C1 110.13(14) . . ?
C2 C3 H3 108.0 . . ?
C2 C3 C1 110.34(14) . . ?
C1 C3 H3 108.0 . . ?
C30 C29 H29 121.3 . . ?
C28 C29 C30 117.33(15) . . ?
C28 C29 H29 121.3 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.44(15) . . ?
C6 C5 H5 119.3 . . ?
F2 C28 C27 117.88(15) . . ?
F2 C28 C29 120.33(14) . . ?
C29 C28 C27 121.77(15) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.61(15) . . ?
C18 C17 H17 120.2 . . ?
C8 C10 H10 107.5 . . ?
C8 C10 C11 110.45(15) . . ?
C8 C10 C12 112.77(14) . . ?
C11 C10 H10 107.5 . . ?
C12 C10 H10 107.5 . . ?
C12 C10 C11 110.92(17) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C35 O1 C32 93.4(6) . . ?
O1 C32 H32A 109.9 . . ?
O1 C32 H32B 109.9 . . ?
H32A C32 H32B 108.3 . . ?
C33 C32 O1 108.7(8) . . ?
C33 C32 H32A 109.9 . . ?
C33 C32 H32B 109.9 . . ?
C32 C33 H33A 116.3 . . ?
C32 C33 H33B 116.3 . . ?
C32 C33 C34 72.9(7) . . ?
H33A C33 H33B 113.3 . . ?
C34 C33 H33A 116.3 . . ?
C34 C33 H33B 116.3 . . ?
C33 C34 H34A 109.8 . . ?
C33 C34 H34B 109.8 . . ?
H34A C34 H34B 108.2 . . ?
C35 C34 C33 109.4(7) . . ?
C35 C34 H34A 109.8 . . ?
C35 C34 H34B 109.8 . . ?
O1 C35 H35A 112.9 . . ?
O1 C35 H35B 112.9 . . ?
C34 C35 O1 94.3(6) . . ?
C34 C35 H35A 112.9 . . ?
C34 C35 H35B 112.9 . . ?
H35A C35 H35B 110.3 . . ?

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
F4 C31 C30 F3 2.7(2) . . . . ?
F4 C31 C30 C29 -176.32(14) . . . . ?
F1 C27 C28 F2 1.9(2) . . . . ?
F1 C27 C28 C29 -176.52(15) . . . . ?
F3 C30 C29 C28 -179.94(14) . . . . ?
N1 C26 C31 F4 -0.8(2) . . . . ?
N1 C26 C31 C30 -179.58(14) . . . . ?
N1 C26 C27 F1 -3.6(2) . . . . ?
N1 C26 C27 C28 176.97(15) . . . . ?
N1 C9 C4 C3 3.5(2) . . . . ?
N1 C9 C4 C5 -178.19(13) . . . . ?
N1 C9 C8 C7 176.32(13) . . . . ?
N1 C9 C8 C10 -6.8(2) . . . . ?
N2 C14 C15 C16 178.74(13) . . . . ?
N2 C14 C15 C20 -3.9(2) . . . . ?
N2 C14 C19 C23 -3.0(2) . . . . ?
N2 C14 C19 C18 -179.29(13) . . . . ?
C13 N1 C26 C31 -53.4(2) . . . . ?
C13 N1 C26 C27 128.39(16) . . . . ?
C13 N1 C9 C4 -69.82(18) . . . . ?
C13 N1 C9 C8 109.31(16) . . . . ?
C13 N2 C14 C15 127.67(15) . . . . ?
C13 N2 C14 C19 -56.39(19) . . . . ?
C26 N1 C13 N2 -7.9(2) . . . . ?
C26 N1 C9 C4 110.82(16) . . . . ?
C26 N1 C9 C8 -70.05(18) . . . . ?
C26 C31 C30 F3 -178.45(14) . . . . ?
C26 C31 C30 C29 2.5(2) . . . . ?
C26 C27 C28 F2 -178.63(14) . . . . ?
C26 C27 C28 C29 2.9(3) . . . . ?
C14 N2 C13 N1 172.35(13) . . . . ?
C14 C15 C16 C17 -0.1(2) . . . . ?
C14 C15 C20 C22 139.21(15) . . . . ?
C14 C15 C20 C21 -95.88(18) . . . . ?
C14 C19 C23 C24 -118.74(16) . . . . ?
C14 C19 C23 C25 117.91(17) . . . . ?
C14 C19 C18 C17 1.6(2) . . . . ?
C9 N1 C13 N2 172.75(14) . . . . ?
C9 N1 C26 C31 125.91(16) . . . . ?
C9 N1 C26 C27 -52.3(2) . . . . ?
C9 C4 C3 C2 -131.02(16) . . . . ?
C9 C4 C3 C1 105.68(17) . . . . ?
C9 C4 C5 C6 1.5(2) . . . . ?
C9 C8 C7 C6 2.3(2) . . . . ?
C9 C8 C10 C11 -117.66(17) . . . . ?
C9 C8 C10 C12 117.60(18) . . . . ?
C15 C14 C19 C23 172.79(14) . . . . ?
C15 C14 C19 C18 -3.5(2) . . . . ?
C15 C16 C17 C18 -1.8(2) . . . . ?
C31 C26 C27 F1 178.14(13) . . . . ?
C31 C26 C27 C28 -1.3(2) . . . . ?
C31 C30 C29 C28 -0.9(3) . . . . ?
C19 C14 C15 C16 2.8(2) . . . . ?
C19 C14 C15 C20 -179.87(13) . . . . ?
C19 C18 C17 C16 1.0(2) . . . . ?
C4 C9 C8 C7 -4.6(2) . . . . ?
C4 C9 C8 C10 172.29(14) . . . . ?
C27 C26 C31 F4 177.45(13) . . . . ?
C27 C26 C31 C30 -1.3(2) . . . . ?
C16 C15 C20 C22 -43.5(2) . . . . ?
C16 C15 C20 C21 81.42(19) . . . . ?
C8 C9 C4 C3 -175.55(14) . . . . ?
C8 C9 C4 C5 2.7(2) . . . . ?
C8 C7 C6 C5 1.6(2) . . . . ?
C7 C8 C10 C11 59.1(2) . . . . ?
C7 C8 C10 C12 -65.6(2) . . . . ?
C7 C6 C5 C4 -3.6(2) . . . . ?
C30 C29 C28 F2 179.83(15) . . . . ?
C30 C29 C28 C27 -1.8(3) . . . . ?
C20 C15 C16 C17 -177.46(14) . . . . ?
C23 C19 C18 C17 -174.88(15) . . . . ?
C18 C19 C23 C24 57.51(19) . . . . ?
C18 C19 C23 C25 -65.84(19) . . . . ?
C3 C4 C5 C6 179.78(14) . . . . ?
C5 C4 C3 C2 50.76(19) . . . . ?
C5 C4 C3 C1 -72.54(18) . . . . ?
C10 C8 C7 C6 -174.60(14) . . . . ?
O1 C32 C33 C34 68.2(9) . . . . ?
C32 O1 C35 C34 -1.3(8) . . . . ?
C32 C33 C34 C35 -71.8(10) . . . . ?
C33 C34 C35 O1 46.4(10) . . . . ?
C35 O1 C32 C33 -52.1(10) . . . . ?

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

data_exp_1249
_database_code_depnum_ccdc_archive 'CCDC 2243052'
loop_
_audit_author_name
_audit_author_address
'Peter Junk'
;James Cook University
Australia
;
_audit_update_record             
;
2023-02-19 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;
_audit_creation_date             2023-02-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C54 H78 F N4 O Pr, C7 H8'
_chemical_formula_sum            'C61 H86 F N4 O Pr'
_chemical_formula_weight         1051.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         PrCHNOF
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'
F F 0.0171 0.0103 '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'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0787(2)
_cell_length_b                   13.8725(2)
_cell_length_c                   33.8375(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.9560(10)
_cell_angle_gamma                90
_cell_volume                     5662.33(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    40121
_cell_measurement_temperature    123.00(12)
_cell_measurement_theta_max      33.4930
_cell_measurement_theta_min      3.3470
_shelx_estimated_absorpt_T_max   0.915
_shelx_estimated_absorpt_T_min   0.840
_exptl_absorpt_coefficient_mu    0.905
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            95583
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.550
_diffrn_reflns_theta_min         3.353
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  46.00   0.50   51.75    --   12.02 -99.00  90.00  138
  2  ω     26.00  75.00   0.50   51.75    --   12.02-151.00   8.00   98
  3  ω     11.00  58.00   0.50   51.75    --   12.02-122.00 169.00   94
  4  ω    -23.00  46.00   0.50   51.75    --   12.02 -99.00 -60.00  138
  5  ω     38.00  85.00   0.50   51.75    --   12.02-178.00-180.00   94
  6  ω    -84.00   2.00   0.50   51.75    --  -12.80 -57.00-180.00  172
  7  ω    -84.00 -59.00   0.50   51.75    --  -12.80 -77.00 -30.00   50
  8  ω    -84.00   2.00   0.50   51.75    --  -12.80 -57.00 120.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0056691000
_diffrn_orient_matrix_UB_12      0.0437206000
_diffrn_orient_matrix_UB_13      0.0107720000
_diffrn_orient_matrix_UB_21      0.0021507000
_diffrn_orient_matrix_UB_22      0.0259990000
_diffrn_orient_matrix_UB_23      -0.0180038000
_diffrn_orient_matrix_UB_31      -0.0584840000
_diffrn_orient_matrix_UB_32      0.0051561000
_diffrn_orient_matrix_UB_33      -0.0007006000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                15222
_reflns_number_total             19825
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.061
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     648
_refine_ls_number_reflns         19825
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+0.9759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0772
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H48(0.4) H48A(0.6) C49(0.4) H49A(0.4) H49B(0.4) H49C(0.4) C62(0.6)
 H62A(0.6) H62B(0.6) H62C(0.6)
3.a Ternary CH refined with riding coordinates:
 C45(H45), C48(H48), C48(H48A), C2(H2), C27(H27), C35(H35), C16(H16), C23(H23),
  C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C54(H54A,H54B), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B)
3.c Aromatic/amide H refined with riding coordinates:
 C41(H41), C43(H43), C42(H42), C32(H32), C30(H30), C31(H31), C19(H19), C5(H5),
 C7(H7), C21(H21), C6(H6), C20(H20), C57(H57), C58(H58), C60(H60), C61(H61),
 C59(H59)
3.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C1(H1A,H1B,H1C), C47(H47A,H47B,H47C), C12(H12A,H12B,
 H12C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C3(H3A,H3B,H3C), C26(H26A,
 H26B,H26C), C46(H46A,H46B,H46C), C37(H37A,H37B,H37C), C11(H11A,H11B,H11C),
 C50(H50A,H50B,H50C), C25(H25A,H25B,H25C), C24(H24A,H24B,H24C), C36(H36A,H36B,
 H36C), C49(H49A,H49B,H49C), C55(H55A,H55B,H55C), C62(H62A,H62B,H62C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pr1 Pr 0.45006(2) 0.58514(2) 0.39578(2) 0.01514(3) Uani 1 1 d . . . . .
F1 F 0.38788(9) 0.50508(7) 0.44332(3) 0.0294(2) Uani 1 1 d . . . . .
O1 O 0.63548(10) 0.57732(9) 0.43160(4) 0.0254(3) Uani 1 1 d . . . . .
N4 N 0.37318(10) 0.48169(9) 0.33922(4) 0.0165(3) Uani 1 1 d . . . . .
N1 N 0.32192(11) 0.71843(9) 0.37733(4) 0.0177(3) Uani 1 1 d . . . . .
N2 N 0.46388(11) 0.75679(10) 0.42129(4) 0.0178(3) Uani 1 1 d . . . . .
N3 N 0.55454(10) 0.52896(10) 0.33855(4) 0.0170(3) Uani 1 1 d . . . . .
C39 C 0.65744(12) 0.52607(11) 0.31963(4) 0.0162(3) Uani 1 1 d . . . . .
C38 C 0.46967(13) 0.47961(11) 0.32254(5) 0.0162(3) Uani 1 1 d . . . . .
C13 C 0.36808(13) 0.78008(11) 0.40322(5) 0.0171(3) Uani 1 1 d . . . . .
C14 C 0.51175(13) 0.81749(11) 0.45185(5) 0.0186(3) Uani 1 1 d . . . . .
C40 C 0.73578(13) 0.45314(12) 0.32936(5) 0.0188(3) Uani 1 1 d . . . . .
C44 C 0.68217(13) 0.59946(11) 0.29258(5) 0.0190(3) Uani 1 1 d . . . . .
C34 C 0.28211(13) 0.43016(11) 0.32099(5) 0.0168(3) Uani 1 1 d . . . . .
C41 C 0.83738(13) 0.45569(13) 0.31141(5) 0.0220(3) Uani 1 1 d . . . . .
H41 H 0.889402 0.407674 0.317259 0.026 Uiso 1 1 calc R U . . .
C45 C 0.71145(14) 0.37213(12) 0.35784(5) 0.0221(3) Uani 1 1 d . . . . .
H45 H 0.642677 0.387828 0.370583 0.027 Uiso 1 1 calc R U . . .
C9 C 0.21871(13) 0.74185(12) 0.35745(5) 0.0192(3) Uani 1 1 d . . . . .
C15 C 0.48137(13) 0.80641(11) 0.49127(5) 0.0199(3) Uani 1 1 d . . . . .
C48 C 0.60018(14) 0.68033(12) 0.28333(5) 0.0232(3) Uani 1 1 d . . . . .
H48 H 0.526226 0.664802 0.292122 0.028 Uiso 0.4 1 calc R U P A 1
H48A H 0.527123 0.652192 0.287212 0.028 Uiso 0.6 1 calc R U P B 2
C33 C 0.24363(14) 0.34692(12) 0.33984(5) 0.0207(3) Uani 1 1 d . . . . .
C4 C 0.12620(13) 0.68274(12) 0.36433(5) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.13806(14) 0.59773(13) 0.39264(5) 0.0246(4) Uani 1 1 d . . . . .
H2 H 0.211024 0.569119 0.389028 0.030 Uiso 1 1 calc R U . . .
C29 C 0.22905(13) 0.46377(12) 0.28565(5) 0.0190(3) Uani 1 1 d . . . . .
C43 C 0.78497(14) 0.59888(12) 0.27583(5) 0.0231(3) Uani 1 1 d . . . . .
H43 H 0.802047 0.647068 0.258027 0.028 Uiso 1 1 calc R U . . .
C27 C 0.26458(14) 0.55587(13) 0.26526(5) 0.0233(3) Uani 1 1 d . . . . .
H27 H 0.313071 0.591690 0.284159 0.028 Uiso 1 1 calc R U . . .
C22 C 0.59559(14) 0.88331(12) 0.44262(5) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.20998(15) 0.81871(12) 0.33036(5) 0.0235(3) Uani 1 1 d . . . . .
C42 C 0.86230(14) 0.52765(13) 0.28525(5) 0.0241(3) Uani 1 1 d . . . . .
H42 H 0.930852 0.528416 0.273939 0.029 Uiso 1 1 calc R U . . .
C32 C 0.15362(14) 0.29720(12) 0.32238(5) 0.0239(3) Uani 1 1 d . . . . .
H32 H 0.127099 0.242575 0.334711 0.029 Uiso 1 1 calc R U . . .
C35 C 0.30375(15) 0.30921(12) 0.37736(5) 0.0243(3) Uani 1 1 d . . . . .
H35 H 0.335469 0.364647 0.391886 0.029 Uiso 1 1 calc R U . . .
C28 C 0.16579(16) 0.62090(14) 0.25350(6) 0.0287(4) Uani 1 1 d . . . . .
H28A H 0.120823 0.590420 0.232876 0.043 Uiso 1 1 calc R U . . .
H28B H 0.192308 0.681602 0.244170 0.043 Uiso 1 1 calc R U . . .
H28C H 0.122346 0.631437 0.276070 0.043 Uiso 1 1 calc R U . . .
C30 C 0.14041(14) 0.41029(12) 0.26895(5) 0.0235(3) Uani 1 1 d . . . . .
H30 H 0.105794 0.430599 0.245206 0.028 Uiso 1 1 calc R U . . .
C16 C 0.38981(15) 0.73823(12) 0.50252(5) 0.0241(3) Uani 1 1 d . . . . .
H16 H 0.379142 0.690300 0.481389 0.029 Uiso 1 1 calc R U . . .
C31 C 0.10310(14) 0.32789(13) 0.28696(5) 0.0253(4) Uani 1 1 d . . . . .
H31 H 0.044198 0.293155 0.275311 0.030 Uiso 1 1 calc R U . . .
C23 C 0.62445(17) 0.90151(14) 0.40030(6) 0.0330(4) Uani 1 1 d . . . . .
H23 H 0.595325 0.847443 0.384279 0.040 Uiso 1 1 calc R U . . .
C19 C 0.53575(15) 0.86253(12) 0.52060(5) 0.0256(4) Uani 1 1 d . . . . .
H19 H 0.515295 0.856923 0.546623 0.031 Uiso 1 1 calc R U . . .
C10 C 0.30911(16) 0.87899(13) 0.31963(5) 0.0273(4) Uani 1 1 d . . . . .
H10 H 0.372961 0.858077 0.336528 0.033 Uiso 1 1 calc R U . . .
C1 C 0.13702(18) 0.63050(17) 0.43567(6) 0.0386(5) Uani 1 1 d . . . . .
H1A H 0.197147 0.674513 0.441238 0.058 Uiso 1 1 calc R U . . .
H1B H 0.145254 0.575502 0.452791 0.058 Uiso 1 1 calc R U . . .
H1C H 0.068016 0.662093 0.440055 0.058 Uiso 1 1 calc R U . . .
C54 C 0.64365(18) 0.57513(16) 0.47484(6) 0.0357(5) Uani 1 1 d . . . . .
H54A H 0.660918 0.510553 0.484271 0.043 Uiso 1 1 calc R U . . .
H54B H 0.574318 0.595375 0.485486 0.043 Uiso 1 1 calc R U . . .
C5 C 0.02433(14) 0.70582(14) 0.34535(6) 0.0271(4) Uani 1 1 d . . . . .
H5 H -0.037765 0.668777 0.350100 0.033 Uiso 1 1 calc R U . . .
C47 C 0.69376(18) 0.27705(13) 0.33525(6) 0.0347(4) Uani 1 1 d . . . . .
H47A H 0.634181 0.284460 0.315590 0.052 Uiso 1 1 calc R U . . .
H47B H 0.675616 0.227009 0.353413 0.052 Uiso 1 1 calc R U . . .
H47C H 0.760420 0.260170 0.322607 0.052 Uiso 1 1 calc R U . . .
C12 C 0.33702(17) 0.86183(16) 0.27662(6) 0.0353(4) Uani 1 1 d . . . . .
H12A H 0.352456 0.794692 0.272791 0.053 Uiso 1 1 calc R U . . .
H12B H 0.400902 0.899300 0.270701 0.053 Uiso 1 1 calc R U . . .
H12C H 0.275223 0.880740 0.259375 0.053 Uiso 1 1 calc R U . . .
C7 C 0.10580(16) 0.83767(14) 0.31190(6) 0.0299(4) Uani 1 1 d . . . . .
H7 H 0.098298 0.888470 0.294023 0.036 Uiso 1 1 calc R U . . .
C21 C 0.64807(16) 0.93611(13) 0.47354(6) 0.0282(4) Uani 1 1 d . . . . .
H21 H 0.704107 0.979138 0.467852 0.034 Uiso 1 1 calc R U . . .
C18 C 0.28048(16) 0.79351(14) 0.50576(6) 0.0321(4) Uani 1 1 d . . . . .
H18A H 0.288850 0.840595 0.526489 0.048 Uiso 1 1 calc R U . . .
H18B H 0.222595 0.749187 0.511697 0.048 Uiso 1 1 calc R U . . .
H18C H 0.261645 0.825285 0.481122 0.048 Uiso 1 1 calc R U . . .
C17 C 0.41720(18) 0.68462(15) 0.54122(6) 0.0350(4) Uani 1 1 d . . . . .
H17A H 0.489447 0.656077 0.540409 0.052 Uiso 1 1 calc R U . . .
H17B H 0.363090 0.635026 0.544633 0.052 Uiso 1 1 calc R U . . .
H17C H 0.416273 0.729066 0.562948 0.052 Uiso 1 1 calc R U . . .
C6 C 0.01450(16) 0.78316(14) 0.31952(6) 0.0310(4) Uani 1 1 d . . . . .
H6 H -0.054087 0.798181 0.307325 0.037 Uiso 1 1 calc R U . . .
C51 C 0.72829(16) 0.63016(17) 0.41717(6) 0.0356(4) Uani 1 1 d . . . . .
H51A H 0.705130 0.693273 0.407566 0.043 Uiso 1 1 calc R U . . .
H51B H 0.761473 0.595375 0.395903 0.043 Uiso 1 1 calc R U . . .
C3 C 0.05241(16) 0.51839(14) 0.38456(7) 0.0339(4) Uani 1 1 d . . . . .
H3A H -0.020217 0.542847 0.389068 0.051 Uiso 1 1 calc R U . . .
H3B H 0.068497 0.464949 0.401942 0.051 Uiso 1 1 calc R U . . .
H3C H 0.055036 0.497457 0.357583 0.051 Uiso 1 1 calc R U . . .
C26 C 0.33086(19) 0.53450(17) 0.22898(7) 0.0404(5) Uani 1 1 d . . . . .
H26A H 0.396218 0.498590 0.236918 0.061 Uiso 1 1 calc R U . . .
H26B H 0.351842 0.594025 0.216987 0.061 Uiso 1 1 calc R U . . .
H26C H 0.286137 0.497455 0.210270 0.061 Uiso 1 1 calc R U . . .
C20 C 0.61904(16) 0.92603(13) 0.51190(6) 0.0292(4) Uani 1 1 d . . . . .
H20 H 0.655163 0.961701 0.531948 0.035 Uiso 1 1 calc R U . . .
C46 C 0.80352(16) 0.36031(15) 0.39016(6) 0.0343(4) Uani 1 1 d . . . . .
H46A H 0.872047 0.345953 0.378249 0.052 Uiso 1 1 calc R U . . .
H46B H 0.785045 0.308540 0.407457 0.052 Uiso 1 1 calc R U . . .
H46C H 0.811308 0.418993 0.405075 0.052 Uiso 1 1 calc R U . . .
C57 C 0.97250(19) 1.14621(17) 0.42222(8) 0.0468(6) Uani 1 1 d . . . . .
H57 H 0.940121 1.204846 0.428276 0.056 Uiso 1 1 calc R U . . .
C37 C 0.39909(18) 0.24405(16) 0.36649(6) 0.0385(5) Uani 1 1 d . . . . .
H37A H 0.369918 0.186840 0.353848 0.058 Uiso 1 1 calc R U . . .
H37B H 0.442247 0.226677 0.390034 0.058 Uiso 1 1 calc R U . . .
H37C H 0.445178 0.277598 0.348742 0.058 Uiso 1 1 calc R U . . .
C56 C 1.03699(19) 1.09995(17) 0.45112(9) 0.0478(6) Uani 1 1 d . . . . .
C11 C 0.2911(2) 0.98665(14) 0.32732(7) 0.0406(5) Uani 1 1 d . . . . .
H11A H 0.228524 1.009037 0.311214 0.061 Uiso 1 1 calc R U . . .
H11B H 0.356012 1.021975 0.320826 0.061 Uiso 1 1 calc R U . . .
H11C H 0.277359 0.996334 0.354730 0.061 Uiso 1 1 calc R U . . .
C50 C 0.5961(2) 0.71232(18) 0.24058(6) 0.0436(5) Uani 1 1 d . . . . .
H50A H 0.666807 0.738396 0.234412 0.065 Uiso 1 1 calc R U . . .
H50B H 0.540012 0.760799 0.236432 0.065 Uiso 1 1 calc R U . . .
H50C H 0.578987 0.658078 0.223738 0.065 Uiso 1 1 calc R U . . .
C25 C 0.7489(2) 0.90734(18) 0.39489(8) 0.0482(6) Uani 1 1 d . . . . .
H25A H 0.778888 0.962571 0.408779 0.072 Uiso 1 1 calc R U . . .
H25B H 0.761905 0.913132 0.367248 0.072 Uiso 1 1 calc R U . . .
H25C H 0.784112 0.850002 0.405258 0.072 Uiso 1 1 calc R U . . .
C24 C 0.5667(2) 0.99363(18) 0.38464(7) 0.0493(6) Uani 1 1 d . . . . .
H24A H 0.488514 0.988890 0.388057 0.074 Uiso 1 1 calc R U . . .
H24B H 0.579515 1.001187 0.357043 0.074 Uiso 1 1 calc R U . . .
H24C H 0.596115 1.048346 0.399033 0.074 Uiso 1 1 calc R U . . .
C36 C 0.22840(19) 0.25551(17) 0.40494(6) 0.0425(5) Uani 1 1 d . . . . .
H36A H 0.165811 0.295241 0.410240 0.064 Uiso 1 1 calc R U . . .
H36B H 0.269039 0.240879 0.429330 0.064 Uiso 1 1 calc R U . . .
H36C H 0.203081 0.196707 0.392540 0.064 Uiso 1 1 calc R U . . .
C52 C 0.80949(18) 0.6391(2) 0.45291(7) 0.0539(7) Uani 1 1 d . . . . .
H52A H 0.858537 0.583736 0.455058 0.065 Uiso 1 1 calc R U . . .
H52B H 0.853610 0.697269 0.451492 0.065 Uiso 1 1 calc R U . . .
C53 C 0.73436(19) 0.6431(2) 0.48709(7) 0.0492(6) Uani 1 1 d . . . . .
H53A H 0.772809 0.622153 0.511467 0.059 Uiso 1 1 calc R U . . .
H53B H 0.705985 0.707725 0.490673 0.059 Uiso 1 1 calc R U . . .
C58 C 0.9540(2) 1.1090(2) 0.38460(10) 0.0590(7) Uani 1 1 d . . . . .
H58 H 0.910896 1.143129 0.365824 0.071 Uiso 1 1 calc R U . . .
C49 C 0.6494(8) 0.7772(6) 0.3042(3) 0.044(2) Uani 0.4 1 d . . P C 1
H49A H 0.661669 0.766259 0.332106 0.066 Uiso 0.4 1 calc R U P C 1
H49B H 0.597391 0.828966 0.299932 0.066 Uiso 0.4 1 calc R U P C 1
H49C H 0.718208 0.793832 0.292992 0.066 Uiso 0.4 1 calc R U P C 1
C60 C 1.0613(2) 0.97345(19) 0.40290(10) 0.0577(7) Uani 1 1 d . . . . .
H60 H 1.090265 0.913800 0.396330 0.069 Uiso 1 1 calc R U . . .
C55 C 1.0619(2) 1.1433(3) 0.49040(9) 0.0698(8) Uani 1 1 d . . . . .
H55A H 1.129990 1.178985 0.490027 0.105 Uiso 1 1 calc R U . . .
H55B H 1.069198 1.093321 0.509964 0.105 Uiso 1 1 calc R U . . .
H55C H 1.002797 1.185961 0.496757 0.105 Uiso 1 1 calc R U . . .
C61 C 1.0826(2) 1.01027(19) 0.44068(10) 0.0592(8) Uani 1 1 d . . . . .
H61 H 1.126770 0.975971 0.459083 0.071 Uiso 1 1 calc R U . . .
C59 C 0.9978(2) 1.0241(2) 0.37505(10) 0.0639(8) Uani 1 1 d . . . . .
H59 H 0.985429 0.999314 0.349667 0.077 Uiso 1 1 calc R U . . .
H13 H 0.3309(14) 0.8413(13) 0.4091(5) 0.012(4) Uiso 1 1 d . . . . .
H38 H 0.4797(15) 0.4430(13) 0.2993(6) 0.018(5) Uiso 1 1 d . . . . .
C62 C 0.6133(5) 0.7564(4) 0.31326(18) 0.0371(12) Uani 0.6 1 d . . P C 2
H62A H 0.602613 0.729734 0.338961 0.056 Uiso 0.6 1 calc R U P C 2
H62B H 0.559454 0.806124 0.307689 0.056 Uiso 0.6 1 calc R U P C 2
H62C H 0.686496 0.783245 0.312740 0.056 Uiso 0.6 1 calc R U P C 2


_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
Pr1 F1 2.1236(11) . ?
Pr1 O1 2.4935(12) . ?
Pr1 N4 2.5298(13) . ?
Pr1 N1 2.4708(13) . ?
Pr1 N2 2.5355(13) . ?
Pr1 N3 2.4902(13) . ?
O1 C54 1.462(2) . ?
O1 C51 1.445(2) . ?
N4 C38 1.321(2) . ?
N4 C34 1.4254(19) . ?
N1 C13 1.326(2) . ?
N1 C9 1.4231(19) . ?
N2 C13 1.321(2) . ?
N2 C14 1.4320(19) . ?
N3 C39 1.428(2) . ?
N3 C38 1.325(2) . ?
C39 C40 1.413(2) . ?
C39 C44 1.411(2) . ?
C38 H38 0.95(2) . ?
C13 H13 0.986(17) . ?
C14 C15 1.410(2) . ?
C14 C22 1.411(2) . ?
C40 C41 1.397(2) . ?
C40 C45 1.519(2) . ?
C44 C48 1.518(2) . ?
C44 C43 1.391(2) . ?
C34 C33 1.409(2) . ?
C34 C29 1.407(2) . ?
C41 H41 0.9300 . ?
C41 C42 1.378(2) . ?
C45 H45 0.9800 . ?
C45 C47 1.534(2) . ?
C45 C46 1.528(2) . ?
C9 C4 1.415(2) . ?
C9 C8 1.407(2) . ?
C15 C16 1.519(2) . ?
C15 C19 1.398(2) . ?
C48 H48 0.9800 . ?
C48 H48A 0.9800 . ?
C48 C50 1.511(3) . ?
C48 C49 1.617(9) . ?
C48 C62 1.466(6) . ?
C33 C32 1.393(2) . ?
C33 C35 1.523(2) . ?
C4 C2 1.522(2) . ?
C4 C5 1.396(2) . ?
C2 H2 0.9800 . ?
C2 C1 1.526(3) . ?
C2 C3 1.526(2) . ?
C29 C27 1.524(2) . ?
C29 C30 1.398(2) . ?
C43 H43 0.9300 . ?
C43 C42 1.386(2) . ?
C27 H27 0.9800 . ?
C27 C28 1.532(2) . ?
C27 C26 1.529(3) . ?
C22 C23 1.512(3) . ?
C22 C21 1.402(2) . ?
C8 C10 1.520(3) . ?
C8 C7 1.401(2) . ?
C42 H42 0.9300 . ?
C32 H32 0.9300 . ?
C32 C31 1.384(2) . ?
C35 H35 0.9800 . ?
C35 C37 1.524(3) . ?
C35 C36 1.530(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C30 H30 0.9300 . ?
C30 C31 1.382(3) . ?
C16 H16 0.9800 . ?
C16 C18 1.536(3) . ?
C16 C17 1.527(3) . ?
C31 H31 0.9300 . ?
C23 H23 0.9800 . ?
C23 C25 1.525(3) . ?
C23 C24 1.537(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(3) . ?
C10 H10 0.9800 . ?
C10 C12 1.529(3) . ?
C10 C11 1.534(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C54 C53 1.488(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(3) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C6 1.373(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.369(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C6 H6 0.9300 . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C51 C52 1.522(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C20 H20 0.9300 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C57 H57 0.9300 . ?
C57 C56 1.377(4) . ?
C57 C58 1.381(4) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C56 C55 1.476(4) . ?
C56 C61 1.413(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C52 C53 1.507(3) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C58 H58 0.9300 . ?
C58 C59 1.338(4) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C60 H60 0.9300 . ?
C60 C61 1.388(4) . ?
C60 C59 1.376(4) . ?
C55 H55A 0.9600 . ?
C55 H55B 0.9600 . ?
C55 H55C 0.9600 . ?
C61 H61 0.9300 . ?
C59 H59 0.9300 . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?

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
F1 Pr1 O1 87.30(4) . . ?
F1 Pr1 N4 98.39(4) . . ?
F1 Pr1 N1 109.96(4) . . ?
F1 Pr1 N2 104.65(4) . . ?
F1 Pr1 N3 129.68(4) . . ?
O1 Pr1 N4 128.94(4) . . ?
O1 Pr1 N2 80.42(4) . . ?
N4 Pr1 N2 143.66(4) . . ?
N1 Pr1 O1 133.68(4) . . ?
N1 Pr1 N4 91.87(4) . . ?
N1 Pr1 N2 54.03(4) . . ?
N1 Pr1 N3 111.94(4) . . ?
N3 Pr1 O1 83.45(4) . . ?
N3 Pr1 N4 54.22(4) . . ?
N3 Pr1 N2 122.11(4) . . ?
C54 O1 Pr1 120.00(11) . . ?
C51 O1 Pr1 120.43(11) . . ?
C51 O1 C54 109.60(14) . . ?
C38 N4 Pr1 92.19(9) . . ?
C38 N4 C34 118.83(13) . . ?
C34 N4 Pr1 148.96(10) . . ?
C13 N1 Pr1 94.54(9) . . ?
C13 N1 C9 119.54(13) . . ?
C9 N1 Pr1 144.32(10) . . ?
C13 N2 Pr1 91.79(9) . . ?
C13 N2 C14 120.13(13) . . ?
C14 N2 Pr1 144.60(10) . . ?
C39 N3 Pr1 147.70(10) . . ?
C38 N3 Pr1 93.86(9) . . ?
C38 N3 C39 118.37(13) . . ?
C40 C39 N3 120.26(14) . . ?
C44 C39 N3 119.27(14) . . ?
C44 C39 C40 120.40(14) . . ?
N4 C38 N3 119.66(14) . . ?
N4 C38 H38 121.2(11) . . ?
N3 C38 H38 119.1(11) . . ?
N1 C13 H13 120.5(10) . . ?
N2 C13 N1 118.46(14) . . ?
N2 C13 H13 121.0(10) . . ?
C15 C14 N2 120.26(14) . . ?
C15 C14 C22 120.33(15) . . ?
C22 C14 N2 119.24(15) . . ?
C39 C40 C45 121.90(15) . . ?
C41 C40 C39 118.25(15) . . ?
C41 C40 C45 119.83(15) . . ?
C39 C44 C48 120.60(14) . . ?
C43 C44 C39 118.90(15) . . ?
C43 C44 C48 120.44(15) . . ?
C33 C34 N4 118.70(14) . . ?
C29 C34 N4 120.61(14) . . ?
C29 C34 C33 120.64(14) . . ?
C40 C41 H41 119.2 . . ?
C42 C41 C40 121.56(16) . . ?
C42 C41 H41 119.2 . . ?
C40 C45 H45 108.1 . . ?
C40 C45 C47 110.28(15) . . ?
C40 C45 C46 112.09(14) . . ?
C47 C45 H45 108.1 . . ?
C46 C45 H45 108.1 . . ?
C46 C45 C47 109.99(15) . . ?
C4 C9 N1 118.04(14) . . ?
C8 C9 N1 121.02(15) . . ?
C8 C9 C4 120.87(14) . . ?
C14 C15 C16 122.24(14) . . ?
C19 C15 C14 118.37(15) . . ?
C19 C15 C16 119.36(15) . . ?
C44 C48 H48 111.7 . . ?
C44 C48 H48A 105.1 . . ?
C44 C48 C49 107.6(4) . . ?
C50 C48 C44 113.75(15) . . ?
C50 C48 H48 111.7 . . ?
C50 C48 H48A 105.1 . . ?
C50 C48 C49 99.6(4) . . ?
C49 C48 H48 111.7 . . ?
C62 C48 C44 110.1(3) . . ?
C62 C48 H48A 105.1 . . ?
C62 C48 C50 116.5(3) . . ?
C34 C33 C35 120.31(14) . . ?
C32 C33 C34 118.82(15) . . ?
C32 C33 C35 120.78(15) . . ?
C9 C4 C2 120.21(14) . . ?
C5 C4 C9 118.46(16) . . ?
C5 C4 C2 121.31(16) . . ?
C4 C2 H2 106.9 . . ?
C4 C2 C1 111.39(16) . . ?
C4 C2 C3 113.91(15) . . ?
C1 C2 H2 106.9 . . ?
C3 C2 H2 106.9 . . ?
C3 C2 C1 110.31(16) . . ?
C34 C29 C27 122.42(14) . . ?
C30 C29 C34 118.27(15) . . ?
C30 C29 C27 119.31(15) . . ?
C44 C43 H43 119.5 . . ?
C42 C43 C44 121.04(16) . . ?
C42 C43 H43 119.5 . . ?
C29 C27 H27 107.6 . . ?
C29 C27 C28 112.18(14) . . ?
C29 C27 C26 111.85(15) . . ?
C28 C27 H27 107.6 . . ?
C26 C27 H27 107.6 . . ?
C26 C27 C28 109.80(15) . . ?
C14 C22 C23 121.40(15) . . ?
C21 C22 C14 118.37(16) . . ?
C21 C22 C23 120.15(16) . . ?
C9 C8 C10 122.64(15) . . ?
C7 C8 C9 117.94(16) . . ?
C7 C8 C10 119.40(16) . . ?
C41 C42 C43 119.84(16) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C33 C32 H32 119.5 . . ?
C31 C32 C33 120.98(16) . . ?
C31 C32 H32 119.5 . . ?
C33 C35 H35 107.8 . . ?
C33 C35 C37 109.65(15) . . ?
C33 C35 C36 113.75(16) . . ?
C37 C35 H35 107.8 . . ?
C37 C35 C36 109.82(17) . . ?
C36 C35 H35 107.8 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C29 C30 H30 119.3 . . ?
C31 C30 C29 121.40(16) . . ?
C31 C30 H30 119.3 . . ?
C15 C16 H16 108.0 . . ?
C15 C16 C18 110.30(15) . . ?
C15 C16 C17 112.94(15) . . ?
C18 C16 H16 108.0 . . ?
C17 C16 H16 108.0 . . ?
C17 C16 C18 109.32(16) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 C32 119.82(15) . . ?
C30 C31 H31 120.1 . . ?
C22 C23 H23 107.6 . . ?
C22 C23 C25 113.51(18) . . ?
C22 C23 C24 110.03(17) . . ?
C25 C23 H23 107.6 . . ?
C25 C23 C24 110.29(18) . . ?
C24 C23 H23 107.6 . . ?
C15 C19 H19 119.2 . . ?
C20 C19 C15 121.65(17) . . ?
C20 C19 H19 119.2 . . ?
C8 C10 H10 107.7 . . ?
C8 C10 C12 110.90(16) . . ?
C8 C10 C11 112.00(16) . . ?
C12 C10 H10 107.7 . . ?
C12 C10 C11 110.69(16) . . ?
C11 C10 H10 107.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C54 H54A 110.5 . . ?
O1 C54 H54B 110.5 . . ?
O1 C54 C53 106.03(18) . . ?
H54A C54 H54B 108.7 . . ?
C53 C54 H54A 110.5 . . ?
C53 C54 H54B 110.5 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.86(17) . . ?
C6 C5 H5 119.6 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C7 H7 119.2 . . ?
C6 C7 C8 121.64(17) . . ?
C6 C7 H7 119.2 . . ?
C22 C21 H21 119.1 . . ?
C20 C21 C22 121.76(17) . . ?
C20 C21 H21 119.1 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.13(16) . . ?
C7 C6 H6 119.9 . . ?
O1 C51 H51A 110.8 . . ?
O1 C51 H51B 110.8 . . ?
O1 C51 C52 104.58(18) . . ?
H51A C51 H51B 108.9 . . ?
C52 C51 H51A 110.8 . . ?
C52 C51 H51B 110.8 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
C27 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.51(16) . . ?
C21 C20 H20 120.2 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C56 C57 H57 118.7 . . ?
C56 C57 C58 122.6(2) . . ?
C58 C57 H57 118.7 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C57 C56 C55 122.1(2) . . ?
C57 C56 C61 116.5(3) . . ?
C61 C56 C55 121.3(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C48 C50 H50A 109.5 . . ?
C48 C50 H50B 109.5 . . ?
C48 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C51 C52 H52A 111.2 . . ?
C51 C52 H52B 111.2 . . ?
H52A C52 H52B 109.1 . . ?
C53 C52 C51 102.93(17) . . ?
C53 C52 H52A 111.2 . . ?
C53 C52 H52B 111.2 . . ?
C54 C53 C52 103.11(19) . . ?
C54 C53 H53A 111.1 . . ?
C54 C53 H53B 111.1 . . ?
C52 C53 H53A 111.1 . . ?
C52 C53 H53B 111.1 . . ?
H53A C53 H53B 109.1 . . ?
C57 C58 H58 119.9 . . ?
C59 C58 C57 120.3(3) . . ?
C59 C58 H58 119.9 . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C61 C60 H60 119.6 . . ?
C59 C60 H60 119.6 . . ?
C59 C60 C61 120.9(3) . . ?
C56 C55 H55A 109.5 . . ?
C56 C55 H55B 109.5 . . ?
C56 C55 H55C 109.5 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C56 C61 H61 120.1 . . ?
C60 C61 C56 119.9(3) . . ?
C60 C61 H61 120.1 . . ?
C58 C59 C60 119.8(3) . . ?
C58 C59 H59 120.1 . . ?
C60 C59 H59 120.1 . . ?
C48 C62 H62A 109.5 . . ?
C48 C62 H62B 109.5 . . ?
C48 C62 H62C 109.5 . . ?
H62A C62 H62B 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 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
Pr1 O1 C54 C53 -136.11(15) . . . . ?
Pr1 O1 C51 C52 159.36(14) . . . . ?
Pr1 N4 C38 N3 -2.84(15) . . . . ?
Pr1 N4 C34 C33 -67.6(2) . . . . ?
Pr1 N4 C34 C29 110.0(2) . . . . ?
Pr1 N1 C13 N2 11.03(15) . . . . ?
Pr1 N1 C9 C4 44.5(3) . . . . ?
Pr1 N1 C9 C8 -132.60(16) . . . . ?
Pr1 N2 C13 N1 -10.71(15) . . . . ?
Pr1 N2 C14 C15 -65.6(2) . . . . ?
Pr1 N2 C14 C22 109.63(19) . . . . ?
Pr1 N3 C39 C40 87.2(2) . . . . ?
Pr1 N3 C39 C44 -89.8(2) . . . . ?
Pr1 N3 C38 N4 2.89(15) . . . . ?
O1 C54 C53 C52 -29.1(2) . . . . ?
O1 C51 C52 C53 -31.4(3) . . . . ?
N4 C34 C33 C32 179.09(15) . . . . ?
N4 C34 C33 C35 -4.3(2) . . . . ?
N4 C34 C29 C27 -0.4(2) . . . . ?
N4 C34 C29 C30 179.78(15) . . . . ?
N1 C9 C4 C2 0.8(2) . . . . ?
N1 C9 C4 C5 179.24(15) . . . . ?
N1 C9 C8 C10 2.0(2) . . . . ?
N1 C9 C8 C7 -179.99(15) . . . . ?
N2 C14 C15 C16 -6.3(2) . . . . ?
N2 C14 C15 C19 175.60(14) . . . . ?
N2 C14 C22 C23 8.9(2) . . . . ?
N2 C14 C22 C21 -174.57(15) . . . . ?
N3 C39 C40 C41 -177.16(14) . . . . ?
N3 C39 C40 C45 4.1(2) . . . . ?
N3 C39 C44 C48 -0.5(2) . . . . ?
N3 C39 C44 C43 176.70(14) . . . . ?
C39 N3 C38 N4 -179.39(14) . . . . ?
C39 C40 C41 C42 0.8(2) . . . . ?
C39 C40 C45 C47 107.71(18) . . . . ?
C39 C40 C45 C46 -129.38(17) . . . . ?
C39 C44 C48 C50 -143.10(18) . . . . ?
C39 C44 C48 C49 107.5(4) . . . . ?
C39 C44 C48 C62 84.0(3) . . . . ?
C39 C44 C43 C42 0.2(2) . . . . ?
C38 N4 C34 C33 109.98(17) . . . . ?
C38 N4 C34 C29 -72.37(19) . . . . ?
C38 N3 C39 C40 -88.54(18) . . . . ?
C38 N3 C39 C44 94.51(18) . . . . ?
C13 N1 C9 C4 -116.44(17) . . . . ?
C13 N1 C9 C8 66.5(2) . . . . ?
C13 N2 C14 C15 85.96(19) . . . . ?
C13 N2 C14 C22 -98.82(18) . . . . ?
C14 N2 C13 N1 -174.69(14) . . . . ?
C14 C15 C16 C18 -96.86(19) . . . . ?
C14 C15 C16 C17 140.48(17) . . . . ?
C14 C15 C19 C20 -1.4(3) . . . . ?
C14 C22 C23 C25 -137.39(18) . . . . ?
C14 C22 C23 C24 98.5(2) . . . . ?
C14 C22 C21 C20 -0.8(3) . . . . ?
C40 C39 C44 C48 -177.43(14) . . . . ?
C40 C39 C44 C43 -0.2(2) . . . . ?
C40 C41 C42 C43 -0.9(3) . . . . ?
C44 C39 C40 C41 -0.2(2) . . . . ?
C44 C39 C40 C45 -179.01(14) . . . . ?
C44 C43 C42 C41 0.4(3) . . . . ?
C34 N4 C38 N3 178.40(14) . . . . ?
C34 C33 C32 C31 0.7(3) . . . . ?
C34 C33 C35 C37 -85.5(2) . . . . ?
C34 C33 C35 C36 151.11(17) . . . . ?
C34 C29 C27 C28 -132.50(17) . . . . ?
C34 C29 C27 C26 103.60(19) . . . . ?
C34 C29 C30 C31 1.8(3) . . . . ?
C41 C40 C45 C47 -71.04(19) . . . . ?
C41 C40 C45 C46 51.9(2) . . . . ?
C45 C40 C41 C42 179.62(15) . . . . ?
C9 N1 C13 N2 180.00(14) . . . . ?
C9 C4 C2 C1 79.0(2) . . . . ?
C9 C4 C2 C3 -155.47(17) . . . . ?
C9 C4 C5 C6 1.8(3) . . . . ?
C9 C8 C10 C12 112.18(19) . . . . ?
C9 C8 C10 C11 -123.61(18) . . . . ?
C9 C8 C7 C6 -0.4(3) . . . . ?
C15 C14 C22 C23 -175.84(16) . . . . ?
C15 C14 C22 C21 0.6(2) . . . . ?
C15 C19 C20 C21 1.3(3) . . . . ?
C48 C44 C43 C42 177.37(16) . . . . ?
C33 C34 C29 C27 177.21(15) . . . . ?
C33 C34 C29 C30 -2.6(2) . . . . ?
C33 C32 C31 C30 -1.5(3) . . . . ?
C4 C9 C8 C10 -175.02(16) . . . . ?
C4 C9 C8 C7 3.0(2) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C2 C4 C5 C6 -179.78(17) . . . . ?
C29 C34 C33 C32 1.4(2) . . . . ?
C29 C34 C33 C35 178.04(15) . . . . ?
C29 C30 C31 C32 0.3(3) . . . . ?
C43 C44 C48 C50 39.8(2) . . . . ?
C43 C44 C48 C49 -69.6(4) . . . . ?
C43 C44 C48 C62 -93.2(3) . . . . ?
C27 C29 C30 C31 -178.07(16) . . . . ?
C22 C14 C15 C16 178.53(15) . . . . ?
C22 C14 C15 C19 0.4(2) . . . . ?
C22 C21 C20 C19 -0.2(3) . . . . ?
C8 C9 C4 C2 177.84(15) . . . . ?
C8 C9 C4 C5 -3.7(2) . . . . ?
C8 C7 C6 C5 -1.5(3) . . . . ?
C32 C33 C35 C37 91.0(2) . . . . ?
C32 C33 C35 C36 -32.4(2) . . . . ?
C35 C33 C32 C31 -175.92(16) . . . . ?
C30 C29 C27 C28 47.3(2) . . . . ?
C30 C29 C27 C26 -76.6(2) . . . . ?
C16 C15 C19 C20 -179.59(16) . . . . ?
C23 C22 C21 C20 175.74(18) . . . . ?
C19 C15 C16 C18 81.23(19) . . . . ?
C19 C15 C16 C17 -41.4(2) . . . . ?
C10 C8 C7 C6 177.68(18) . . . . ?
C54 O1 C51 C52 13.8(2) . . . . ?
C5 C4 C2 C1 -99.47(19) . . . . ?
C5 C4 C2 C3 26.1(2) . . . . ?
C7 C8 C10 C12 -65.8(2) . . . . ?
C7 C8 C10 C11 58.4(2) . . . . ?
C21 C22 C23 C25 46.2(2) . . . . ?
C21 C22 C23 C24 -78.0(2) . . . . ?
C51 O1 C54 C53 9.6(2) . . . . ?
C51 C52 C53 C54 37.0(3) . . . . ?
C57 C56 C61 C60 0.0(4) . . . . ?
C57 C58 C59 C60 0.2(4) . . . . ?
C56 C57 C58 C59 1.1(4) . . . . ?
C58 C57 C56 C55 176.0(3) . . . . ?
C58 C57 C56 C61 -1.2(4) . . . . ?
C55 C56 C61 C60 -177.2(3) . . . . ?
C61 C60 C59 C58 -1.4(4) . . . . ?
C59 C60 C61 C56 1.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.599
_oxdiff_exptl_absorpt_empirical_full_min 0.835
# start Validation Reply Form
_vrf_PLAT910_exp_1249            
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         22 Note  
RESPONSE: Low-angle reflections rejected because of beam stop and
high background scattering.
;
# end Validation Reply Form
