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

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

data_p21onn_a
_database_code_depnum_ccdc_archive 'CCDC 1913266'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2019-04-30 deposited with the CCDC.	2021-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H28 Bi2 N8 O8, 2(N O3)'
_chemical_formula_sum            'C32 H28 Bi2 N10 O14'
_chemical_formula_weight         1194.60

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0626(5)
_cell_length_b                   13.5522(6)
_cell_length_c                   11.9227(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.194(2)
_cell_angle_gamma                90
_cell_volume                     1782.70(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7938
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      26.18

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.225
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.103
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    9.944
_shelx_estimated_absorpt_T_min   0.427
_shelx_estimated_absorpt_T_max   0.606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6042
_exptl_absorpt_correction_T_max  0.7361
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23111
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.380
_diffrn_reflns_theta_max         26.419
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3652
_reflns_number_gt                2845
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/4 (Bruker, 2014) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXle (Sheldrick, 2011)'
_computing_publication_material  'enCIFer V1.6.1. (IUCr, 2017)'
_refine_special_details          
; 
Structure was phased by direct methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F². A final analysis of variance between observed 
and calculated structure factors showed some dependence on amplitude 
and little dependence on resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0080P)²+4.2861P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3652
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0461
_refine_ls_wR_factor_gt          0.0417
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.48971(2) 0.56062(2) 0.35468(2) 0.01184(6) Uani 1 1 d . . . . .
C11 C 0.2592(5) 0.6351(4) 0.4941(4) 0.0165(12) Uani 1 1 d . . . . .
H11 H 0.324687 0.657916 0.543286 0.020 Uiso 1 1 calc R U . . .
C12 C 0.1430(4) 0.6523(4) 0.5220(4) 0.0164(12) Uani 1 1 d . . . . .
H12 H 0.128256 0.686468 0.589239 0.020 Uiso 1 1 calc R U . . .
C13 C 0.0474(5) 0.6188(4) 0.4503(4) 0.0195(12) Uani 1 1 d . . . . .
H13 H -0.034062 0.628562 0.468094 0.023 Uiso 1 1 calc R U . . .
C14 C 0.0728(4) 0.5710(4) 0.3524(4) 0.0205(12) Uani 1 1 d . . . . .
H14 H 0.008528 0.547494 0.302307 0.025 Uiso 1 1 calc R U . . .
C15 C 0.1916(4) 0.5574(4) 0.3273(4) 0.0145(10) Uani 1 1 d . . . . .
C16 C 0.2253(4) 0.5082(4) 0.2229(4) 0.0141(11) Uani 1 1 d . . . . .
C17 C 0.1390(4) 0.4863(4) 0.1356(4) 0.0172(12) Uani 1 1 d . . . . .
H17 H 0.056684 0.504896 0.139984 0.021 Uiso 1 1 calc R U . . .
C18 C 0.1752(4) 0.4371(4) 0.0428(4) 0.0176(11) Uani 1 1 d . . . . .
H18 H 0.117510 0.420997 -0.017355 0.021 Uiso 1 1 calc R U . . .
C19 C 0.2952(4) 0.4112(4) 0.0372(4) 0.0183(12) Uani 1 1 d . . . . .
H19 H 0.320688 0.375820 -0.025707 0.022 Uiso 1 1 calc R U . . .
C110 C 0.3780(4) 0.4376(4) 0.1251(4) 0.0122(10) Uani 1 1 d . . . . .
C111 C 0.5081(5) 0.4123(3) 0.1242(4) 0.0162(12) Uani 1 1 d . . . . .
C112 C 0.5546(4) 0.3606(3) 0.0365(4) 0.0170(12) Uani 1 1 d . . . . .
H112 H 0.503376 0.342161 -0.027466 0.020 Uiso 1 1 calc R U . . .
C113 C 0.6767(5) 0.3360(4) 0.0432(4) 0.0186(12) Uani 1 1 d . . . . .
H113 H 0.709416 0.299642 -0.015560 0.022 Uiso 1 1 calc R U . . .
C114 C 0.7499(5) 0.3647(4) 0.1355(4) 0.0185(12) Uani 1 1 d . . . . .
H114 H 0.833609 0.348231 0.142091 0.022 Uiso 1 1 calc R U . . .
C115 C 0.6985(4) 0.4182(4) 0.2184(4) 0.0173(12) Uani 1 1 d . . . . .
H115 H 0.749315 0.439422 0.281524 0.021 Uiso 1 1 calc R U . . .
N11 N 0.2841(3) 0.5873(3) 0.3998(3) 0.0139(9) Uani 1 1 d . . . . .
N12 N 0.3423(4) 0.4857(3) 0.2155(3) 0.0132(9) Uani 1 1 d . . . . .
N13 N 0.5813(3) 0.4414(3) 0.2144(3) 0.0140(9) Uani 1 1 d . . . . .
N21 N 0.4365(4) 0.7684(3) 0.2625(3) 0.0175(10) Uani 1 1 d . . . . .
O21 O 0.3845(3) 0.6940(3) 0.2156(3) 0.0186(8) Uani 1 1 d . . . . .
O22 O 0.4714(3) 0.7615(2) 0.3653(3) 0.0174(8) Uani 1 1 d . . . . .
O23 O 0.4522(3) 0.8446(3) 0.2087(3) 0.0258(9) Uani 1 1 d . . . . .
N31 N 0.7427(4) 0.6436(3) 0.2653(4) 0.0194(10) Uani 1 1 d . . . . .
O31 O 0.6422(3) 0.6644(3) 0.2130(3) 0.0181(8) Uani 1 1 d . . . . .
O32 O 0.7418(3) 0.6077(3) 0.3634(3) 0.0213(8) Uani 1 1 d . . . . .
O33 O 0.8382(3) 0.6581(3) 0.2208(3) 0.0340(10) Uani 1 1 d . . . . .
O41 O 0.4694(3) 0.4202(2) 0.4482(2) 0.0133(8) Uani 1 1 d . . . . .
C41 C 0.4060(5) 0.3349(4) 0.4049(4) 0.0233(13) Uani 1 1 d . . . . .
H41A H 0.321755 0.352513 0.382497 0.035 Uiso 1 1 calc R U . . .
H41B H 0.407715 0.283761 0.463042 0.035 Uiso 1 1 calc R U . . .
H41C H 0.445126 0.310030 0.339380 0.035 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 O41 2.225(3) . ?
Bi1 O41 2.375(3) 3_666 ?
Bi1 N11 2.402(4) . ?
Bi1 N12 2.459(4) . ?
Bi1 N13 2.585(4) . ?
Bi1 O21 2.663(3) . ?
Bi1 O22 2.734(3) . ?
C11 N11 1.343(6) . ?
C11 C12 1.372(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(6) . ?
C14 H14 0.9500 . ?
C15 N11 1.353(6) . ?
C15 C16 1.483(6) . ?
C16 N12 1.339(6) . ?
C16 C17 1.393(6) . ?
C17 C18 1.375(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(7) . ?
C18 H18 0.9500 . ?
C19 C110 1.387(6) . ?
C19 H19 0.9500 . ?
C110 N12 1.344(6) . ?
C110 C111 1.480(7) . ?
C111 N13 1.357(6) . ?
C111 C112 1.388(6) . ?
C112 C113 1.387(7) . ?
C112 H112 0.9500 . ?
C113 C114 1.374(7) . ?
C113 H113 0.9500 . ?
C114 C115 1.382(7) . ?
C114 H114 0.9500 . ?
C115 N13 1.332(6) . ?
C115 H115 0.9500 . ?
N21 O23 1.235(5) . ?
N21 O22 1.261(5) . ?
N21 O21 1.270(5) . ?
N31 O33 1.232(5) . ?
N31 O32 1.267(5) . ?
N31 O31 1.267(5) . ?
O41 C41 1.429(5) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 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
O41 Bi1 O41 67.44(13) . 3_666 ?
O41 Bi1 N11 83.35(12) . . ?
O41 Bi1 N11 82.94(12) 3_666 . ?
O41 Bi1 N12 84.19(12) . . ?
O41 Bi1 N12 141.43(12) 3_666 . ?
N11 Bi1 N12 67.74(13) . . ?
O41 Bi1 N13 81.29(12) . . ?
O41 Bi1 N13 130.78(11) 3_666 . ?
N11 Bi1 N13 131.38(12) . . ?
N12 Bi1 N13 65.00(12) . . ?
O41 Bi1 O21 146.83(11) . . ?
O41 Bi1 O21 125.82(10) 3_666 . ?
N11 Bi1 O21 70.10(11) . . ?
N12 Bi1 O21 67.79(12) . . ?
N13 Bi1 O21 101.27(11) . . ?
O41 Bi1 O22 144.85(10) . . ?
O41 Bi1 O22 81.64(10) 3_666 . ?
N11 Bi1 O22 76.42(11) . . ?
N12 Bi1 O22 113.24(11) . . ?
N13 Bi1 O22 133.35(11) . . ?
O21 Bi1 O22 47.33(10) . . ?
N11 C11 C12 122.6(5) . . ?
N11 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C11 C12 C13 118.7(5) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 118.7(5) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C15 C14 C13 120.1(5) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
N11 C15 C14 120.5(4) . . ?
N11 C15 C16 116.5(4) . . ?
C14 C15 C16 123.0(4) . . ?
N12 C16 C17 121.0(4) . . ?
N12 C16 C15 117.5(4) . . ?
C17 C16 C15 121.5(4) . . ?
C18 C17 C16 118.7(5) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 C19 120.0(4) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C110 118.8(5) . . ?
C18 C19 H19 120.6 . . ?
C110 C19 H19 120.6 . . ?
N12 C110 C19 121.0(4) . . ?
N12 C110 C111 117.5(4) . . ?
C19 C110 C111 121.6(4) . . ?
N13 C111 C112 120.7(5) . . ?
N13 C111 C110 116.8(4) . . ?
C112 C111 C110 122.5(4) . . ?
C113 C112 C111 119.4(5) . . ?
C113 C112 H112 120.3 . . ?
C111 C112 H112 120.3 . . ?
C114 C113 C112 119.5(5) . . ?
C114 C113 H113 120.2 . . ?
C112 C113 H113 120.2 . . ?
C113 C114 C115 118.2(5) . . ?
C113 C114 H114 120.9 . . ?
C115 C114 H114 120.9 . . ?
N13 C115 C114 123.3(5) . . ?
N13 C115 H115 118.4 . . ?
C114 C115 H115 118.4 . . ?
C11 N11 C15 119.2(4) . . ?
C11 N11 Bi1 121.0(3) . . ?
C15 N11 Bi1 119.7(3) . . ?
C16 N12 C110 120.4(4) . . ?
C16 N12 Bi1 117.3(3) . . ?
C110 N12 Bi1 121.5(3) . . ?
C115 N13 C111 118.9(4) . . ?
C115 N13 Bi1 123.4(3) . . ?
C111 N13 Bi1 117.1(3) . . ?
O23 N21 O22 121.5(4) . . ?
O23 N21 O21 120.8(4) . . ?
O22 N21 O21 117.7(4) . . ?
N21 O21 Bi1 95.8(2) . . ?
N21 O22 Bi1 92.7(3) . . ?
O33 N31 O32 121.6(4) . . ?
O33 N31 O31 120.1(4) . . ?
O32 N31 O31 118.3(4) . . ?
C41 O41 Bi1 125.1(3) . . ?
C41 O41 Bi1 119.9(3) . 3_666 ?
Bi1 O41 Bi1 112.56(13) . 3_666 ?
O41 C41 H41A 109.5 . . ?
O41 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O41 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?

_refine_diff_density_max         2.297
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.172



####################################################################### 
# 
# 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_c2onc_a
_database_code_depnum_ccdc_archive 'CCDC 1913267'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2019-04-30 deposited with the CCDC.	2021-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H19 Bi F6 N4 O7 S2'
_chemical_formula_sum            'C31 H19 Bi F6 N4 O7 S2'
_chemical_formula_weight         946.60

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   36.9899(17)
_cell_length_b                   9.7296(4)
_cell_length_c                   18.0256(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.543(2)
_cell_angle_gamma                90
_cell_volume                     6487.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9764
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      25.42

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.938
_exptl_crystal_F_000             3664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.023
_exptl_absorpt_coefficient_mu    5.654
_shelx_estimated_absorpt_T_min   0.630
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70209
_exptl_absorpt_correction_T_max  0.89840
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38810
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.164
_diffrn_reflns_theta_max         25.779
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6206
_reflns_number_gt                4371
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/4 (Bruker, 2014) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXle (Sheldrick, 2011)'
_computing_publication_material  'enCIFer V1.6.1. (IUCr, 2017)'
_refine_special_details          
;Structure was phased by direct methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F². A final analysis of variance between observed 
and calculated structure factors showed some dependence on amplitude 
and little dependence on resolution.,Disorder on both thiophene and one CF3 groups
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0299P)²+34.5561P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6206
_refine_ls_number_parameters     580
_refine_ls_number_restraints     539
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.34156(2) 0.55133(2) 0.59869(2) 0.02326(9) Uani 1 1 d . . . . .
N11 N 0.34084(15) 0.3825(5) 0.4928(3) 0.0247(13) Uani 1 1 d . . . . .
N12 N 0.30996(13) 0.6331(5) 0.4823(3) 0.0184(12) Uani 1 1 d . . . . .
N13 N 0.31248(13) 0.7889(5) 0.6074(3) 0.0193(12) Uani 1 1 d . . . . .
C11 C 0.35399(18) 0.2552(7) 0.5027(4) 0.0276(16) Uani 1 1 d . . . . .
H11 H 0.366860 0.234964 0.547182 0.033 Uiso 1 1 calc R U . . .
C12 C 0.34950(18) 0.1525(7) 0.4505(4) 0.0306(17) Uani 1 1 d . . . . .
H12 H 0.359233 0.063471 0.458911 0.037 Uiso 1 1 calc R U . . .
C13 C 0.33081(18) 0.1810(7) 0.3864(4) 0.0294(17) Uani 1 1 d . . . . .
H13 H 0.327479 0.112112 0.349636 0.035 Uiso 1 1 calc R U . . .
C14 C 0.31685(19) 0.3114(6) 0.3760(4) 0.0288(17) Uani 1 1 d . . . . .
H14 H 0.303229 0.332162 0.332528 0.035 Uiso 1 1 calc R U . . .
C15 C 0.32277(17) 0.4118(6) 0.4292(3) 0.0217(15) Uani 1 1 d . . . . .
C16 C 0.30855(16) 0.5538(7) 0.4217(3) 0.0206(14) Uani 1 1 d . . . . .
C17 C 0.29437(18) 0.6011(7) 0.3549(4) 0.0254(16) Uani 1 1 d . . . . .
H17 H 0.294176 0.543467 0.312343 0.030 Uiso 1 1 calc R U . . .
C18 C 0.28075(18) 0.7310(7) 0.3508(4) 0.0276(16) Uani 1 1 d . . . . .
H18 H 0.270452 0.763808 0.305669 0.033 Uiso 1 1 calc R U . . .
C19 C 0.28201(18) 0.8149(7) 0.4127(4) 0.0283(17) Uani 1 1 d . . . . .
H19 H 0.272732 0.905848 0.410784 0.034 Uiso 1 1 calc R U . . .
C110 C 0.29713(17) 0.7632(6) 0.4778(3) 0.0209(15) Uani 1 1 d . . . . .
C111 C 0.29804(16) 0.8485(6) 0.5468(3) 0.0209(14) Uani 1 1 d . . . . .
C112 C 0.28468(18) 0.9814(6) 0.5493(4) 0.0258(16) Uani 1 1 d . . . . .
H112 H 0.274617 1.022542 0.506004 0.031 Uiso 1 1 calc R U . . .
C113 C 0.28608(17) 1.0534(7) 0.6151(4) 0.0277(15) Uani 1 1 d . . . . .
H113 H 0.277563 1.145394 0.617313 0.033 Uiso 1 1 calc R U . . .
C114 C 0.29986(19) 0.9910(7) 0.6772(4) 0.0297(17) Uani 1 1 d . . . . .
H114 H 0.300146 1.037201 0.723609 0.036 Uiso 1 1 calc R U . . .
C115 C 0.31334(18) 0.8593(6) 0.6708(4) 0.0262(16) Uani 1 1 d . . . . .
H115 H 0.323686 0.816937 0.713531 0.031 Uiso 1 1 calc R U . . .
C21 C 0.3776(2) 0.1854(7) 0.7611(4) 0.0325(18) Uani 1 1 d . . . . .
C22 C 0.37000(19) 0.3344(7) 0.7367(4) 0.0287(16) Uani 1 1 d . . . . .
C23 C 0.38887(19) 0.4345(7) 0.7758(4) 0.0304(17) Uani 1 1 d . . . . .
H23 H 0.404167 0.403814 0.815093 0.036 Uiso 1 1 calc R U . . .
C24 C 0.38758(19) 0.5771(7) 0.7631(4) 0.0316(18) Uani 1 1 d D . . . .
C25A C 0.40922(19) 0.6679(7) 0.8114(4) 0.0342(14) Uani 0.750(7) 1 d D U P A 1
C26A C 0.4237(7) 0.636(2) 0.8813(11) 0.037(2) Uani 0.750(7) 1 d D U P A 1
H26A H 0.421064 0.550692 0.906326 0.044 Uiso 0.750(7) 1 calc R U P A 1
C27A C 0.4434(4) 0.7534(11) 0.9094(7) 0.042(2) Uani 0.750(7) 1 d D U P A 1
H27A H 0.455772 0.753469 0.955829 0.051 Uiso 0.750(7) 1 calc R U P A 1
C28A C 0.4426(4) 0.8622(12) 0.8640(6) 0.041(2) Uani 0.750(7) 1 d D U P A 1
H28A H 0.454052 0.947503 0.874437 0.049 Uiso 0.750(7) 1 calc R U P A 1
S21A S 0.41810(19) 0.8283(4) 0.7842(3) 0.0416(10) Uani 0.750(7) 1 d D U P A 1
C25B C 0.40922(19) 0.6679(7) 0.8114(4) 0.0342(14) Uani 0.250(7) 1 d D U P A 2
C26B C 0.417(2) 0.801(4) 0.786(3) 0.038(3) Uani 0.250(7) 1 d D U P A 2
H26C H 0.409510 0.837600 0.739136 0.046 Uiso 0.250(7) 1 calc R U P A 2
C27B C 0.4386(11) 0.873(2) 0.8404(16) 0.041(3) Uani 0.250(7) 1 d D U P A 2
H27B H 0.446594 0.964878 0.834330 0.049 Uiso 0.250(7) 1 calc R U P A 2
C28B C 0.4460(11) 0.798(2) 0.9007(16) 0.040(3) Uani 0.250(7) 1 d D U P A 2
H28B H 0.460287 0.828590 0.941463 0.048 Uiso 0.250(7) 1 calc R U P A 2
S21B S 0.4265(6) 0.6366(19) 0.8950(8) 0.038(2) Uani 0.250(7) 1 d D U P A 2
F21 F 0.37778(12) 0.1022(4) 0.7018(2) 0.0430(11) Uani 1 1 d . . . . .
F22 F 0.35251(11) 0.1379(4) 0.8064(2) 0.0425(11) Uani 1 1 d . . . . .
F23 F 0.40963(11) 0.1688(4) 0.7955(2) 0.0471(12) Uani 1 1 d . . . . .
O21 O 0.34707(12) 0.3473(4) 0.6859(2) 0.0296(11) Uani 1 1 d . . . . .
O22 O 0.37069(12) 0.6366(4) 0.7107(2) 0.0279(11) Uani 1 1 d . . . . .
C32 C 0.4130(2) 0.7289(7) 0.5576(4) 0.0362(19) Uani 1 1 d D . . . .
C33 C 0.4387(2) 0.6403(8) 0.5842(5) 0.056(3) Uani 1 1 d . . . . .
H33 H 0.462217 0.674862 0.595060 0.067 Uiso 1 1 calc R U . . .
C34 C 0.4317(2) 0.4991(7) 0.5963(4) 0.038(2) Uani 1 1 d D . . . .
C35A C 0.4622(3) 0.3971(12) 0.5979(9) 0.043(2) Uani 0.551(6) 1 d D U P B 1
C36A C 0.5007(3) 0.4236(11) 0.5940(7) 0.028(2) Uani 0.551(6) 1 d D U P B 1
H36A H 0.512259 0.509822 0.587090 0.034 Uiso 0.551(6) 1 calc R U P B 1
C37A C 0.5175(4) 0.2926(14) 0.6026(8) 0.050(3) Uani 0.551(6) 1 d D U P B 1
H37A H 0.542927 0.281055 0.599108 0.059 Uiso 0.551(6) 1 calc R U P B 1
C38A C 0.4955(4) 0.1875(15) 0.6159(9) 0.055(3) Uani 0.551(6) 1 d D U P B 1
H38A H 0.503548 0.096289 0.624918 0.066 Uiso 0.551(6) 1 calc R U P B 1
S31A S 0.4522(2) 0.2339(8) 0.6149(4) 0.0585(17) Uani 0.551(6) 1 d D U P B 1
C35B C 0.4619(4) 0.4244(14) 0.6367(10) 0.039(3) Uani 0.449(6) 1 d D U P B 2
C36B C 0.4948(4) 0.4665(14) 0.6744(8) 0.030(3) Uani 0.449(6) 1 d D U P B 2
H36B H 0.502788 0.558645 0.680218 0.037 Uiso 0.449(6) 1 calc R U P B 2
C37B C 0.5130(4) 0.3488(16) 0.7012(10) 0.047(3) Uani 0.449(6) 1 d D U P B 2
H37B H 0.534397 0.354330 0.730603 0.057 Uiso 0.449(6) 1 calc R U P B 2
C38B C 0.4981(4) 0.2304(17) 0.6822(10) 0.051(3) Uani 0.449(6) 1 d D U P B 2
H38B H 0.508776 0.143212 0.691643 0.062 Uiso 0.449(6) 1 calc R U P B 2
S31B S 0.4588(3) 0.2520(10) 0.6402(5) 0.0544(19) Uani 0.449(6) 1 d D U P B 2
C31A C 0.4242(4) 0.8802(12) 0.5494(11) 0.050(3) Uani 0.53(3) 1 d D U P C 1
F31A F 0.4003(4) 0.9630(18) 0.5834(9) 0.054(3) Uani 0.53(3) 1 d D U P C 1
F32A F 0.4230(4) 0.9108(16) 0.4771(9) 0.061(3) Uani 0.53(3) 1 d D U P C 1
F33A F 0.4569(3) 0.9119(12) 0.5746(11) 0.058(3) Uani 0.53(3) 1 d D U P C 1
C31B C 0.4238(4) 0.8706(14) 0.5269(12) 0.051(3) Uani 0.47(3) 1 d D U P C 2
F31B F 0.4059(5) 0.971(2) 0.5628(11) 0.055(4) Uani 0.47(3) 1 d D U P C 2
F32B F 0.4152(4) 0.8901(17) 0.4552(9) 0.051(4) Uani 0.47(3) 1 d D U P C 2
F33B F 0.4590(3) 0.8966(14) 0.5338(13) 0.059(4) Uani 0.47(3) 1 d D U P C 2
O31 O 0.38002(13) 0.7082(5) 0.5434(3) 0.0331(12) Uani 1 1 d . . . . .
O32 O 0.40186(13) 0.4464(5) 0.5912(3) 0.0323(11) Uani 1 1 d . . . . .
O41 O 0.28484(12) 0.5431(4) 0.6928(2) 0.0280(10) Uani 1 1 d . . . . .
O42 O 0.28014(12) 0.4161(4) 0.5945(2) 0.0271(11) Uani 1 1 d . . . . .
O43 O 0.24810(13) 0.3685(5) 0.6919(3) 0.0367(12) Uani 1 1 d . . . . .
N41 N 0.27073(15) 0.4404(6) 0.6608(3) 0.0246(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O31 2.318(5) . ?
Bi1 O22 2.426(4) . ?
Bi1 O32 2.458(5) . ?
Bi1 N11 2.518(5) . ?
Bi1 N12 2.521(5) . ?
Bi1 O21 2.538(4) . ?
Bi1 N13 2.555(5) . ?
Bi1 O42 2.626(4) . ?
Bi1 O41 2.711(4) . ?
N11 C11 1.342(8) . ?
N11 C15 1.352(8) . ?
N12 C16 1.337(7) . ?
N12 C110 1.355(8) . ?
N13 C115 1.333(7) . ?
N13 C111 1.344(7) . ?
C11 C12 1.381(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.368(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.484(9) . ?
C16 C17 1.388(8) . ?
C17 C18 1.362(9) . ?
C17 H17 0.9500 . ?
C18 C19 1.383(9) . ?
C18 H18 0.9500 . ?
C19 C110 1.389(8) . ?
C19 H19 0.9500 . ?
C110 C111 1.494(8) . ?
C111 C112 1.384(9) . ?
C112 C113 1.378(9) . ?
C112 H112 0.9500 . ?
C113 C114 1.367(9) . ?
C113 H113 0.9500 . ?
C114 C115 1.380(9) . ?
C114 H114 0.9500 . ?
C115 H115 0.9500 . ?
C21 F22 1.326(8) . ?
C21 F21 1.340(8) . ?
C21 F23 1.341(7) . ?
C21 C22 1.540(9) . ?
C22 O21 1.249(7) . ?
C22 C23 1.387(9) . ?
C23 C24 1.407(9) . ?
C23 H23 0.9500 . ?
C24 O22 1.267(8) . ?
C24 C25A 1.471(9) . ?
C24 C25B 1.471(9) . ?
C25A C26A 1.40(2) . ?
C25A S21A 1.670(7) . ?
C26A C27A 1.44(2) . ?
C26A H26A 0.9500 . ?
C27A C28A 1.338(12) . ?
C27A H27A 0.9500 . ?
C28A S21A 1.724(10) . ?
C28A H28A 0.9500 . ?
C25B C26B 1.41(2) . ?
C25B S21B 1.660(10) . ?
C26B C27B 1.44(3) . ?
C26B H26C 0.9500 . ?
C27B C28B 1.337(15) . ?
C27B H27B 0.9500 . ?
C28B S21B 1.727(14) . ?
C28B H28B 0.9500 . ?
C32 O31 1.259(8) . ?
C32 C33 1.368(10) . ?
C32 C31A 1.537(12) . ?
C32 C31B 1.540(13) . ?
C33 C34 1.416(11) . ?
C33 H33 0.9500 . ?
C34 O32 1.218(8) . ?
C34 C35A 1.502(12) . ?
C34 C35B 1.514(12) . ?
C35A C36A 1.451(15) . ?
C35A S31A 1.659(12) . ?
C36A C37A 1.426(15) . ?
C36A H36A 0.9500 . ?
C37A C38A 1.331(16) . ?
C37A H37A 0.9500 . ?
C38A S31A 1.663(13) . ?
C38A H38A 0.9500 . ?
C35B C36B 1.447(16) . ?
C35B S31B 1.683(13) . ?
C36B C37B 1.412(16) . ?
C36B H36B 0.9500 . ?
C37B C38B 1.321(18) . ?
C37B C37B 2.01(3) 2_656 ?
C37B H37B 0.9500 . ?
C38B S31B 1.648(15) . ?
C38B H38B 0.9500 . ?
C31A F33A 1.326(12) . ?
C31A F32A 1.336(13) . ?
C31A F31A 1.348(12) . ?
C31B F33B 1.329(12) . ?
C31B F32B 1.342(14) . ?
C31B F31B 1.349(13) . ?
O41 N41 1.263(6) . ?
O42 N41 1.271(6) . ?
O43 N41 1.231(7) . ?

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
O31 Bi1 O22 82.12(16) . . ?
O31 Bi1 O32 71.87(16) . . ?
O22 Bi1 O32 77.96(15) . . ?
O31 Bi1 N11 96.07(17) . . ?
O22 Bi1 N11 148.80(16) . . ?
O32 Bi1 N11 71.98(16) . . ?
O31 Bi1 N12 73.51(16) . . ?
O22 Bi1 N12 141.59(14) . . ?
O32 Bi1 N12 119.96(15) . . ?
N11 Bi1 N12 64.75(16) . . ?
O31 Bi1 O21 137.29(15) . . ?
O22 Bi1 O21 73.73(14) . . ?
O32 Bi1 O21 69.00(15) . . ?
N11 Bi1 O21 87.67(16) . . ?
N12 Bi1 O21 142.72(15) . . ?
O31 Bi1 N13 72.02(16) . . ?
O22 Bi1 N13 79.82(15) . . ?
O32 Bi1 N13 139.63(16) . . ?
N11 Bi1 N13 129.44(16) . . ?
N12 Bi1 N13 64.76(16) . . ?
O21 Bi1 N13 134.48(15) . . ?
O31 Bi1 O42 148.42(15) . . ?
O22 Bi1 O42 124.95(14) . . ?
O32 Bi1 O42 125.15(14) . . ?
N11 Bi1 O42 69.41(16) . . ?
N12 Bi1 O42 74.92(14) . . ?
O21 Bi1 O42 71.97(13) . . ?
N13 Bi1 O42 95.19(14) . . ?
O31 Bi1 O41 140.37(15) . . ?
O22 Bi1 O41 80.20(14) . . ?
O32 Bi1 O41 136.88(14) . . ?
N11 Bi1 O41 116.88(15) . . ?
N12 Bi1 O41 100.05(14) . . ?
O21 Bi1 O41 69.37(14) . . ?
N13 Bi1 O41 70.10(15) . . ?
O42 Bi1 O41 47.84(13) . . ?
C11 N11 C15 118.9(5) . . ?
C11 N11 Bi1 120.0(4) . . ?
C15 N11 Bi1 120.4(4) . . ?
C16 N12 C110 118.6(5) . . ?
C16 N12 Bi1 120.8(4) . . ?
C110 N12 Bi1 120.3(4) . . ?
C115 N13 C111 118.8(5) . . ?
C115 N13 Bi1 120.7(4) . . ?
C111 N13 Bi1 120.3(4) . . ?
N11 C11 C12 122.5(6) . . ?
N11 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C13 C12 C11 119.0(6) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 119.0(6) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 119.9(6) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
N11 C15 C14 120.8(6) . . ?
N11 C15 C16 116.5(5) . . ?
C14 C15 C16 122.7(6) . . ?
N12 C16 C17 122.0(6) . . ?
N12 C16 C15 116.8(5) . . ?
C17 C16 C15 121.2(6) . . ?
C18 C17 C16 119.4(6) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 119.6(6) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C110 118.6(6) . . ?
C18 C19 H19 120.7 . . ?
C110 C19 H19 120.7 . . ?
N12 C110 C19 121.8(6) . . ?
N12 C110 C111 117.7(5) . . ?
C19 C110 C111 120.5(6) . . ?
N13 C111 C112 121.0(6) . . ?
N13 C111 C110 116.3(5) . . ?
C112 C111 C110 122.7(6) . . ?
C113 C112 C111 119.5(6) . . ?
C113 C112 H112 120.2 . . ?
C111 C112 H112 120.2 . . ?
C114 C113 C112 119.3(6) . . ?
C114 C113 H113 120.4 . . ?
C112 C113 H113 120.4 . . ?
C113 C114 C115 118.5(6) . . ?
C113 C114 H114 120.8 . . ?
C115 C114 H114 120.8 . . ?
N13 C115 C114 122.8(6) . . ?
N13 C115 H115 118.6 . . ?
C114 C115 H115 118.6 . . ?
F22 C21 F21 106.8(6) . . ?
F22 C21 F23 107.1(6) . . ?
F21 C21 F23 106.6(6) . . ?
F22 C21 C22 112.1(6) . . ?
F21 C21 C22 110.0(6) . . ?
F23 C21 C22 113.8(6) . . ?
O21 C22 C23 129.6(6) . . ?
O21 C22 C21 115.2(6) . . ?
C23 C22 C21 115.2(6) . . ?
C22 C23 C24 126.4(6) . . ?
C22 C23 H23 116.8 . . ?
C24 C23 H23 116.8 . . ?
O22 C24 C23 126.0(6) . . ?
O22 C24 C25A 115.4(6) . . ?
C23 C24 C25A 118.5(6) . . ?
O22 C24 C25B 115.4(6) . . ?
C23 C24 C25B 118.5(6) . . ?
C26A C25A C24 127.0(11) . . ?
C26A C25A S21A 113.3(10) . . ?
C24 C25A S21A 119.7(5) . . ?
C25A C26A C27A 109.2(17) . . ?
C25A C26A H26A 125.4 . . ?
C27A C26A H26A 125.4 . . ?
C28A C27A C26A 113.8(13) . . ?
C28A C27A H27A 123.1 . . ?
C26A C27A H27A 123.1 . . ?
C27A C28A S21A 111.6(10) . . ?
C27A C28A H28A 124.2 . . ?
S21A C28A H28A 124.2 . . ?
C25A S21A C28A 92.1(5) . . ?
C26B C25B C24 118.0(15) . . ?
C26B C25B S21B 112.9(11) . . ?
C24 C25B S21B 129.0(8) . . ?
C25B C26B C27B 109.5(19) . . ?
C25B C26B H26C 125.2 . . ?
C27B C26B H26C 125.2 . . ?
C28B C27B C26B 113.5(18) . . ?
C28B C27B H27B 123.3 . . ?
C26B C27B H27B 123.3 . . ?
C27B C28B S21B 111.5(14) . . ?
C27B C28B H28B 124.3 . . ?
S21B C28B H28B 124.3 . . ?
C25B S21B C28B 92.6(8) . . ?
C22 O21 Bi1 125.7(4) . . ?
C24 O22 Bi1 132.5(4) . . ?
O31 C32 C33 129.8(7) . . ?
O31 C32 C31A 113.3(8) . . ?
C33 C32 C31A 116.7(9) . . ?
O31 C32 C31B 109.0(8) . . ?
C33 C32 C31B 120.4(9) . . ?
C32 C33 C34 122.4(8) . . ?
C32 C33 H33 118.8 . . ?
C34 C33 H33 118.8 . . ?
O32 C34 C33 124.4(7) . . ?
O32 C34 C35A 113.7(8) . . ?
C33 C34 C35A 120.3(8) . . ?
O32 C34 C35B 119.8(8) . . ?
C33 C34 C35B 113.8(9) . . ?
C36A C35A C34 128.3(10) . . ?
C36A C35A S31A 113.5(8) . . ?
C34 C35A S31A 117.9(9) . . ?
C37A C36A C35A 105.3(10) . . ?
C37A C36A H36A 127.4 . . ?
C35A C36A H36A 127.4 . . ?
C38A C37A C36A 116.1(12) . . ?
C38A C37A H37A 122.0 . . ?
C36A C37A H37A 122.0 . . ?
C37A C38A S31A 112.4(11) . . ?
C37A C38A H38A 123.8 . . ?
S31A C38A H38A 123.8 . . ?
C35A S31A C38A 92.7(7) . . ?
C36B C35B C34 134.7(12) . . ?
C36B C35B S31B 108.8(9) . . ?
C34 C35B S31B 116.5(10) . . ?
C37B C36B C35B 109.1(12) . . ?
C37B C36B H36B 125.4 . . ?
C35B C36B H36B 125.4 . . ?
C38B C37B C36B 115.0(14) . . ?
C38B C37B C37B 91.4(12) . 2_656 ?
C36B C37B C37B 93.9(11) . 2_656 ?
C38B C37B H37B 122.5 . . ?
C36B C37B H37B 122.5 . . ?
C37B C37B H37B 85.1 2_656 . ?
C37B C38B S31B 111.9(12) . . ?
C37B C38B H38B 124.1 . . ?
S31B C38B H38B 124.1 . . ?
C38B S31B C35B 94.8(8) . . ?
F33A C31A F32A 107.8(11) . . ?
F33A C31A F31A 107.8(11) . . ?
F32A C31A F31A 107.1(10) . . ?
F33A C31A C32 115.8(11) . . ?
F32A C31A C32 107.5(13) . . ?
F31A C31A C32 110.5(13) . . ?
F33B C31B F32B 106.7(11) . . ?
F33B C31B F31B 107.5(12) . . ?
F32B C31B F31B 104.3(10) . . ?
F33B C31B C32 113.3(12) . . ?
F32B C31B C32 114.3(13) . . ?
F31B C31B C32 110.2(15) . . ?
C32 O31 Bi1 128.0(4) . . ?
C34 O32 Bi1 130.0(5) . . ?
N41 O41 Bi1 93.3(3) . . ?
N41 O42 Bi1 97.1(4) . . ?
O43 N41 O41 121.4(5) . . ?
O43 N41 O42 121.1(6) . . ?
O41 N41 O42 117.4(5) . . ?

_refine_diff_density_max         1.620
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.148



_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_pbar1
_database_code_depnum_ccdc_archive 'CCDC 1913270'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2019-04-30 deposited with the CCDC.	2021-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H19 Bi Br F6 N3 O4 S2'
_chemical_formula_sum            'C31 H19 Bi Br F6 N3 O4 S2'
_chemical_formula_weight         964.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.2659(6)
_cell_length_b                   10.8192(6)
_cell_length_c                   14.9442(8)
_cell_angle_alpha                91.545(2)
_cell_angle_beta                 92.281(2)
_cell_angle_gamma                109.003(2)
_cell_volume                     1566.73(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    9648
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      26.39

_exptl_crystal_description       'thick needle'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.045
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    7.114
_shelx_estimated_absorpt_T_min   0.286
_shelx_estimated_absorpt_T_max   0.726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3212
_exptl_absorpt_correction_T_max  0.7942
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48006
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.993
_diffrn_reflns_theta_max         26.414
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6436
_reflns_number_gt                6196
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/4 (Bruker, 2014) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXle (Sheldrick, 2011)'
_computing_publication_material  'enCIFer V1.6.1. (IUCr, 2017)'
_refine_special_details          
;Structure was phased by direct methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F². A final analysis of variance between observed 
and calculated structure factors showed some dependence on amplitude 
and little dependence on resolution.,Disorder on one thiophene group
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0113P)²+1.9603P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6435
_refine_ls_number_parameters     470
_refine_ls_number_restraints     104
_refine_ls_R_factor_all          0.0157
_refine_ls_R_factor_gt           0.0144
_refine_ls_wR_factor_ref         0.0338
_refine_ls_wR_factor_gt          0.0334
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.69895(2) 0.79207(2) 0.30777(2) 0.00935(3) Uani 1 1 d . . . . .
Br1 Br 0.45249(2) 0.78343(2) 0.37728(2) 0.01573(5) Uani 1 1 d . . . . .
S11 S 0.51438(6) 0.30181(5) 0.39263(4) 0.01441(11) Uani 1 1 d . . . . .
F11 F 0.30195(18) 0.52900(16) 0.02572(11) 0.0420(5) Uani 1 1 d . . . . .
F12 F 0.35712(16) 0.73187(15) 0.06630(10) 0.0311(4) Uani 1 1 d . . . . .
F13 F 0.49236(16) 0.66608(16) -0.01293(9) 0.0311(4) Uani 1 1 d . . . . .
O11 O 0.58801(17) 0.71653(15) 0.16130(10) 0.0166(3) Uani 1 1 d . . . . .
O12 O 0.58870(16) 0.55350(14) 0.31107(10) 0.0141(3) Uani 1 1 d . . . . .
C11 C 0.4079(3) 0.6329(2) 0.05434(16) 0.0213(5) Uani 1 1 d . . . . .
C12 C 0.4848(2) 0.6148(2) 0.13999(14) 0.0141(4) Uani 1 1 d . . . . .
C13 C 0.4380(2) 0.4972(2) 0.18036(15) 0.0146(4) Uani 1 1 d . . . . .
H13 H 0.359785 0.431012 0.153512 0.018 Uiso 1 1 calc R U . . .
C14 C 0.5009(2) 0.4694(2) 0.26063(14) 0.0111(4) Uani 1 1 d . . . . .
C15 C 0.4624(2) 0.3330(2) 0.28723(14) 0.0116(4) Uani 1 1 d . . . . .
C16 C 0.3933(2) 0.2176(2) 0.23642(15) 0.0117(4) Uani 1 1 d . . . . .
H16 H 0.355055 0.214278 0.177103 0.014 Uiso 1 1 calc R U . . .
C17 C 0.3886(2) 0.1060(2) 0.28645(16) 0.0166(5) Uani 1 1 d . . . . .
H17 H 0.347230 0.018644 0.263396 0.020 Uiso 1 1 calc R U . . .
C18 C 0.4490(2) 0.1368(2) 0.37037(16) 0.0162(5) Uani 1 1 d . . . . .
H18 H 0.454192 0.073572 0.412005 0.019 Uiso 1 1 calc R U . . .
F21 F 0.9488(2) 0.49385(16) 0.15995(12) 0.0421(4) Uani 1 1 d . . . . .
F22 F 1.02876(18) 0.51756(16) 0.29526(11) 0.0371(4) Uani 1 1 d . . . . .
F23 F 1.15820(18) 0.61097(17) 0.19154(15) 0.0509(5) Uani 1 1 d . . . . .
O21 O 0.88634(18) 0.67846(16) 0.28715(12) 0.0220(4) Uani 1 1 d . . . . .
O22 O 0.92668(16) 0.94414(15) 0.24516(11) 0.0173(3) Uani 1 1 d . . . . .
C21 C 1.0316(3) 0.5816(2) 0.21945(18) 0.0237(5) Uani 1 1 d . . . . .
C22 C 0.9807(2) 0.6988(2) 0.23321(15) 0.0157(5) Uani 1 1 d . . . . .
C23 C 1.0421(2) 0.8072(2) 0.18385(15) 0.0175(5) Uani 1 1 d . . . . .
H23 H 1.110429 0.803250 0.143843 0.021 Uiso 1 1 calc R U . . .
C24 C 1.0080(2) 0.9233(2) 0.19024(14) 0.0142(4) Uani 1 1 d . . . . .
C25 C 1.0712(2) 1.0297(2) 0.13005(15) 0.0170(5) Uani 1 1 d D . . . .
C26A C 1.1610(17) 1.0280(18) 0.0607(11) 0.018(2) Uani 0.630(3) 1 d D U P A 1
H26A H 1.196522 0.959145 0.047289 0.022 Uiso 0.630(3) 1 calc R U P A 1
C27A C 1.1900(10) 1.1493(6) 0.0132(7) 0.0212(13) Uani 0.630(3) 1 d D U P A 1
H27A H 1.247575 1.169253 -0.036204 0.025 Uiso 0.630(3) 1 calc R U P A 1
C28A C 1.1262(9) 1.2306(9) 0.0470(4) 0.0209(16) Uani 0.630(3) 1 d D U P A 1
H28A H 1.134734 1.313896 0.024291 0.025 Uiso 0.630(3) 1 calc R U P A 1
S21A S 1.0287(4) 1.1664(2) 0.1349(3) 0.0195(4) Uani 0.630(3) 1 d D U P A 1
C26B C 1.036(2) 1.1465(16) 0.1369(16) 0.022(3) Uani 0.370(3) 1 d D U P A 2
H26B H 0.976910 1.164188 0.179195 0.027 Uiso 0.370(3) 1 calc R U P A 2
C27B C 1.1054(15) 1.2345(15) 0.0684(8) 0.018(2) Uani 0.370(3) 1 d D U P A 2
H27B H 1.096331 1.318105 0.060003 0.022 Uiso 0.370(3) 1 calc R U P A 2
C28B C 1.1841(17) 1.1840(10) 0.0182(12) 0.020(2) Uani 0.370(3) 1 d D U P A 2
H28B H 1.236644 1.227957 -0.029303 0.024 Uiso 0.370(3) 1 calc R U P A 2
S21B S 1.1780(8) 1.0318(8) 0.0500(5) 0.0197(9) Uani 0.370(3) 1 d D U P A 2
C31 C 0.6298(2) 1.0043(2) 0.16312(15) 0.0175(5) Uani 1 1 d . . . . .
H31 H 0.587750 0.923557 0.130393 0.021 Uiso 1 1 calc R U . . .
C32 C 0.6373(3) 1.1192(2) 0.12191(16) 0.0196(5) Uani 1 1 d . . . . .
H32 H 0.599939 1.117457 0.062532 0.024 Uiso 1 1 calc R U . . .
C33 C 0.7004(2) 1.2363(2) 0.16889(16) 0.0181(5) Uani 1 1 d . . . . .
H33 H 0.708589 1.316904 0.142001 0.022 Uiso 1 1 calc R U . . .
C34 C 0.7515(2) 1.2349(2) 0.25593(15) 0.0152(4) Uani 1 1 d . . . . .
H34 H 0.795506 1.314603 0.289328 0.018 Uiso 1 1 calc R U . . .
C35 C 0.7380(2) 1.1156(2) 0.29402(14) 0.0116(4) Uani 1 1 d . . . . .
C36 C 0.7862(2) 1.1075(2) 0.38814(14) 0.0112(4) Uani 1 1 d . . . . .
C37 C 0.8268(2) 1.2167(2) 0.44712(15) 0.0135(4) Uani 1 1 d . . . . .
H37 H 0.823906 1.298820 0.428014 0.016 Uiso 1 1 calc R U . . .
C38 C 0.8712(2) 1.2039(2) 0.53369(15) 0.0151(4) Uani 1 1 d . . . . .
H38 H 0.900694 1.277727 0.574433 0.018 Uiso 1 1 calc R U . . .
C39 C 0.8724(2) 1.0835(2) 0.56078(15) 0.0135(4) Uani 1 1 d . . . . .
H39 H 0.903068 1.073425 0.620128 0.016 Uiso 1 1 calc R U . . .
C310 C 0.8281(2) 0.9767(2) 0.49969(14) 0.0104(4) Uani 1 1 d . . . . .
C311 C 0.8218(2) 0.8431(2) 0.52511(14) 0.0112(4) Uani 1 1 d . . . . .
C312 C 0.8612(2) 0.8171(2) 0.61087(14) 0.0132(4) Uani 1 1 d . . . . .
H312 H 0.898291 0.886302 0.654670 0.016 Uiso 1 1 calc R U . . .
C313 C 0.8458(2) 0.6895(2) 0.63169(15) 0.0154(5) Uani 1 1 d . . . . .
H313 H 0.869743 0.670066 0.690452 0.018 Uiso 1 1 calc R U . . .
C314 C 0.7952(2) 0.5905(2) 0.56642(15) 0.0160(5) Uani 1 1 d . . . . .
H314 H 0.783176 0.502131 0.579429 0.019 Uiso 1 1 calc R U . . .
C315 C 0.7628(2) 0.6235(2) 0.48178(15) 0.0153(5) Uani 1 1 d . . . . .
H315 H 0.731176 0.556411 0.436000 0.018 Uiso 1 1 calc R U . . .
N31 N 0.67897(19) 1.00186(17) 0.24696(12) 0.0123(4) Uani 1 1 d . . . . .
N32 N 0.78610(18) 0.98966(17) 0.41468(12) 0.0100(3) Uani 1 1 d . . . . .
N33 N 0.77396(18) 0.74612(17) 0.46169(12) 0.0115(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 O11 2.4196(15) . ?
Bi1 O12 2.4606(15) . ?
Bi1 N33 2.5102(18) . ?
Bi1 N32 2.5257(17) . ?
Bi1 N31 2.5336(18) . ?
Bi1 O22 2.6077(16) . ?
Bi1 O21 2.6216(16) . ?
Bi1 Br1 2.7477(3) . ?
S11 C18 1.708(2) . ?
S11 C15 1.720(2) . ?
F11 C11 1.331(3) . ?
F12 C11 1.345(3) . ?
F13 C11 1.333(3) . ?
O11 C12 1.276(3) . ?
O12 C14 1.258(3) . ?
C11 C12 1.528(3) . ?
C12 C13 1.372(3) . ?
C13 C14 1.425(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.468(3) . ?
C15 C16 1.403(3) . ?
C16 C17 1.425(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.360(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
F21 C21 1.335(3) . ?
F22 C21 1.340(3) . ?
F23 C21 1.321(3) . ?
O21 C22 1.253(3) . ?
O22 C24 1.260(3) . ?
C21 C22 1.533(3) . ?
C22 C23 1.385(3) . ?
C23 C24 1.411(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.474(3) . ?
C25 C26A 1.419(13) . ?
C25 C26B 1.425(14) . ?
C25 S21B 1.650(6) . ?
C25 S21A 1.673(3) . ?
C26A C27A 1.458(16) . ?
C26A H26A 0.9500 . ?
C27A C28A 1.354(7) . ?
C27A H27A 0.9500 . ?
C28A S21A 1.706(7) . ?
C28A H28A 0.9500 . ?
C26B C27B 1.461(18) . ?
C26B H26B 0.9500 . ?
C27B C28B 1.352(9) . ?
C27B H27B 0.9500 . ?
C28B S21B 1.708(10) . ?
C28B H28B 0.9500 . ?
C31 N31 1.336(3) . ?
C31 C32 1.383(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.378(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.386(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.392(3) . ?
C34 H34 0.9500 . ?
C35 N31 1.345(3) . ?
C35 C36 1.487(3) . ?
C36 N32 1.345(3) . ?
C36 C37 1.392(3) . ?
C37 C38 1.380(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.378(3) . ?
C38 H38 0.9500 . ?
C39 C310 1.393(3) . ?
C39 H39 0.9500 . ?
C310 N32 1.351(3) . ?
C310 C311 1.486(3) . ?
C311 N33 1.347(3) . ?
C311 C312 1.392(3) . ?
C312 C313 1.383(3) . ?
C312 H312 0.9500 . ?
C313 C314 1.382(3) . ?
C313 H313 0.9500 . ?
C314 C315 1.381(3) . ?
C314 H314 0.9500 . ?
C315 N33 1.337(3) . ?
C315 H315 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 Bi1 O12 72.56(5) . . ?
O11 Bi1 N33 150.61(5) . . ?
O12 Bi1 N33 78.31(5) . . ?
O11 Bi1 N32 143.62(5) . . ?
O12 Bi1 N32 139.61(5) . . ?
N33 Bi1 N32 65.12(6) . . ?
O11 Bi1 N31 78.62(5) . . ?
O12 Bi1 N31 145.11(5) . . ?
N33 Bi1 N31 129.97(6) . . ?
N32 Bi1 N31 65.06(6) . . ?
O11 Bi1 O22 94.45(5) . . ?
O12 Bi1 O22 134.30(5) . . ?
N33 Bi1 O22 103.28(5) . . ?
N32 Bi1 O22 73.46(5) . . ?
N31 Bi1 O22 66.25(5) . . ?
O11 Bi1 O21 93.45(6) . . ?
O12 Bi1 O21 70.94(5) . . ?
N33 Bi1 O21 73.14(6) . . ?
N32 Bi1 O21 111.44(6) . . ?
N31 Bi1 O21 130.94(5) . . ?
O22 Bi1 O21 66.27(5) . . ?
O11 Bi1 Br1 91.55(4) . . ?
O12 Bi1 Br1 80.47(4) . . ?
N33 Bi1 Br1 87.33(4) . . ?
N32 Bi1 Br1 81.28(4) . . ?
N31 Bi1 Br1 81.09(4) . . ?
O22 Bi1 Br1 144.78(4) . . ?
O21 Bi1 Br1 147.92(4) . . ?
C18 S11 C15 91.53(11) . . ?
C12 O11 Bi1 128.78(14) . . ?
C14 O12 Bi1 134.11(14) . . ?
F11 C11 F13 107.3(2) . . ?
F11 C11 F12 106.5(2) . . ?
F13 C11 F12 105.81(19) . . ?
F11 C11 C12 115.06(19) . . ?
F13 C11 C12 111.3(2) . . ?
F12 C11 C12 110.39(19) . . ?
O11 C12 C13 130.3(2) . . ?
O11 C12 C11 111.45(19) . . ?
C13 C12 C11 118.2(2) . . ?
C12 C13 C14 123.2(2) . . ?
C12 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
O12 C14 C13 124.8(2) . . ?
O12 C14 C15 116.74(19) . . ?
C13 C14 C15 118.43(19) . . ?
C16 C15 C14 129.2(2) . . ?
C16 C15 S11 112.09(16) . . ?
C14 C15 S11 118.59(16) . . ?
C15 C16 C17 110.3(2) . . ?
C15 C16 H16 124.8 . . ?
C17 C16 H16 124.8 . . ?
C18 C17 C16 113.5(2) . . ?
C18 C17 H17 123.3 . . ?
C16 C17 H17 123.3 . . ?
C17 C18 S11 112.52(17) . . ?
C17 C18 H18 123.7 . . ?
S11 C18 H18 123.7 . . ?
C22 O21 Bi1 130.65(14) . . ?
C24 O22 Bi1 132.27(14) . . ?
F23 C21 F21 107.0(2) . . ?
F23 C21 F22 106.8(2) . . ?
F21 C21 F22 105.4(2) . . ?
F23 C21 C22 114.8(2) . . ?
F21 C21 C22 110.9(2) . . ?
F22 C21 C22 111.3(2) . . ?
O21 C22 C23 130.5(2) . . ?
O21 C22 C21 113.1(2) . . ?
C23 C22 C21 116.4(2) . . ?
C22 C23 C24 123.1(2) . . ?
C22 C23 H23 118.5 . . ?
C24 C23 H23 118.5 . . ?
O22 C24 C23 124.5(2) . . ?
O22 C24 C25 116.4(2) . . ?
C23 C24 C25 119.1(2) . . ?
C26A C25 C24 127.0(8) . . ?
C26B C25 C24 118.7(8) . . ?
C26B C25 S21B 113.0(7) . . ?
C24 C25 S21B 128.2(3) . . ?
C26A C25 S21A 113.1(7) . . ?
C24 C25 S21A 119.7(2) . . ?
C25 C26A C27A 108.8(13) . . ?
C25 C26A H26A 125.6 . . ?
C27A C26A H26A 125.6 . . ?
C28A C27A C26A 113.0(11) . . ?
C28A C27A H27A 123.5 . . ?
C26A C27A H27A 123.5 . . ?
C27A C28A S21A 112.3(8) . . ?
C27A C28A H28A 123.8 . . ?
S21A C28A H28A 123.8 . . ?
C25 S21A C28A 92.8(4) . . ?
C25 C26B C27B 108.9(14) . . ?
C25 C26B H26B 125.6 . . ?
C27B C26B H26B 125.6 . . ?
C28B C27B C26B 112.6(16) . . ?
C28B C27B H27B 123.7 . . ?
C26B C27B H27B 123.7 . . ?
C27B C28B S21B 112.1(14) . . ?
C27B C28B H28B 123.9 . . ?
S21B C28B H28B 123.9 . . ?
C25 S21B C28B 93.4(7) . . ?
N31 C31 C32 122.8(2) . . ?
N31 C31 H31 118.6 . . ?
C32 C31 H31 118.6 . . ?
C33 C32 C31 118.5(2) . . ?
C33 C32 H32 120.7 . . ?
C31 C32 H32 120.7 . . ?
C32 C33 C34 119.1(2) . . ?
C32 C33 H33 120.5 . . ?
C34 C33 H33 120.5 . . ?
C33 C34 C35 119.5(2) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
N31 C35 C34 121.0(2) . . ?
N31 C35 C36 117.01(18) . . ?
C34 C35 C36 121.9(2) . . ?
N32 C36 C37 121.3(2) . . ?
N32 C36 C35 117.23(19) . . ?
C37 C36 C35 121.48(19) . . ?
C38 C37 C36 119.1(2) . . ?
C38 C37 H37 120.4 . . ?
C36 C37 H37 120.4 . . ?
C39 C38 C37 119.7(2) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C38 C39 C310 118.9(2) . . ?
C38 C39 H39 120.5 . . ?
C310 C39 H39 120.5 . . ?
N32 C310 C39 121.33(19) . . ?
N32 C310 C311 116.76(18) . . ?
C39 C310 C311 121.89(19) . . ?
N33 C311 C312 120.6(2) . . ?
N33 C311 C310 117.19(18) . . ?
C312 C311 C310 122.19(19) . . ?
C313 C312 C311 119.4(2) . . ?
C313 C312 H312 120.3 . . ?
C311 C312 H312 120.3 . . ?
C314 C313 C312 119.5(2) . . ?
C314 C313 H313 120.2 . . ?
C312 C313 H313 120.2 . . ?
C315 C314 C313 118.2(2) . . ?
C315 C314 H314 120.9 . . ?
C313 C314 H314 120.9 . . ?
N33 C315 C314 122.6(2) . . ?
N33 C315 H315 118.7 . . ?
C314 C315 H315 118.7 . . ?
C31 N31 C35 119.04(19) . . ?
C31 N31 Bi1 120.63(14) . . ?
C35 N31 Bi1 119.50(14) . . ?
C36 N32 C310 119.64(18) . . ?
C36 N32 Bi1 120.09(14) . . ?
C310 N32 Bi1 120.23(13) . . ?
C315 N33 C311 119.57(19) . . ?
C315 N33 Bi1 119.71(14) . . ?
C311 N33 Bi1 120.70(14) . . ?

_refine_diff_density_max         1.176
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.075



_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_c2onc_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1913271'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2019-04-30 deposited with the CCDC.	2021-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H19 Eu F6 N4 O7 S2'
_chemical_formula_sum            'C31 H19 Eu F6 N4 O7 S2'
_chemical_formula_weight         889.58

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'
Eu Eu -0.1578 3.6682 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   37.6364(16)
_cell_length_b                   9.6744(4)
_cell_length_c                   18.2345(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.9090(10)
_cell_angle_gamma                90
_cell_volume                     6604.1(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9767
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.40
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_F_000             3504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.048
_exptl_absorpt_coefficient_mu    2.114
_shelx_estimated_absorpt_T_min   0.611
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72416
_exptl_absorpt_correction_T_max  0.92594
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43671
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.393
_diffrn_reflns_theta_max         26.445
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6796
_reflns_number_gt                5886
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 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.
;

_computing_data_collection       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-1 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
;Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The highest peaks in the final difference Fourier 
map were in the vicinity of the Eu atom; the final map had no other 
significant features.  A final analysis of variance between observed and 
calculated structure factors showed little dependence on amplitude and 
resolution.,SQUEEZE,Disorder on both thiophene groups; partially occupied (30%) MeOH solvent squeezed
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0240P)²+32.1792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6796
_refine_ls_number_parameters     543
_refine_ls_number_restraints     322
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0652
_refine_ls_wR_factor_gt          0.0622
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.34120(2) 0.44851(2) 0.61592(2) 0.01482(5) Uani 1 1 d . . . . .
N11 N 0.31051(7) 0.2117(3) 0.61705(14) 0.0158(5) Uani 1 1 d . . . . .
N12 N 0.30900(6) 0.3637(3) 0.49269(13) 0.0137(5) Uani 1 1 d . . . . .
N13 N 0.33949(7) 0.6165(3) 0.50856(14) 0.0171(5) Uani 1 1 d . . . . .
C11 C 0.31023(8) 0.1409(3) 0.68014(17) 0.0206(7) Uani 1 1 d . . . . .
H11 H 0.319488 0.184389 0.724776 0.025 Uiso 1 1 calc R U . . .
C12 C 0.29720(9) 0.0082(3) 0.68361(18) 0.0215(7) Uani 1 1 d . . . . .
H12 H 0.297581 -0.038354 0.729562 0.026 Uiso 1 1 calc R U . . .
C13 C 0.28363(9) -0.0558(3) 0.61932(18) 0.0216(7) Uani 1 1 d . . . . .
H13 H 0.274809 -0.147765 0.619956 0.026 Uiso 1 1 calc R U . . .
C14 C 0.28309(8) 0.0164(3) 0.55390(18) 0.0188(7) Uani 1 1 d . . . . .
H14 H 0.273538 -0.025127 0.508918 0.023 Uiso 1 1 calc R U . . .
C15 C 0.29658(8) 0.1498(3) 0.55420(17) 0.0154(6) Uani 1 1 d . . . . .
C16 C 0.29633(8) 0.2330(3) 0.48573(16) 0.0145(6) Uani 1 1 d . . . . .
C17 C 0.28269(8) 0.1800(3) 0.41768(17) 0.0189(7) Uani 1 1 d . . . . .
H17 H 0.273976 0.087804 0.414046 0.023 Uiso 1 1 calc R U . . .
C18 C 0.28185(8) 0.2615(3) 0.35553(17) 0.0208(7) Uani 1 1 d . . . . .
H18 H 0.272367 0.226718 0.308858 0.025 Uiso 1 1 calc R U . . .
C19 C 0.29502(8) 0.3944(3) 0.36227(17) 0.0186(7) Uani 1 1 d . . . . .
H19 H 0.295080 0.452196 0.320153 0.022 Uiso 1 1 calc R U . . .
C110 C 0.30825(8) 0.4429(3) 0.43189(16) 0.0147(6) Uani 1 1 d . . . . .
C111 C 0.32184(8) 0.5869(3) 0.44227(17) 0.0167(6) Uani 1 1 d . . . . .
C112 C 0.31615(9) 0.6854(3) 0.38711(18) 0.0219(7) Uani 1 1 d . . . . .
H112 H 0.303189 0.662707 0.341228 0.026 Uiso 1 1 calc R U . . .
C113 C 0.32960(9) 0.8173(4) 0.39977(18) 0.0236(7) Uani 1 1 d . . . . .
H113 H 0.326135 0.885983 0.362493 0.028 Uiso 1 1 calc R U . . .
C114 C 0.34810(9) 0.8481(3) 0.46702(19) 0.0228(7) Uani 1 1 d . . . . .
H114 H 0.357760 0.937690 0.476811 0.027 Uiso 1 1 calc R U . . .
C115 C 0.35222(9) 0.7451(3) 0.51986(18) 0.0222(7) Uani 1 1 d . . . . .
H115 H 0.364684 0.766543 0.566451 0.027 Uiso 1 1 calc R U . . .
F21 F 0.35174(5) 0.8678(2) 0.81210(11) 0.0293(5) Uani 1 1 d . . . . .
F22 F 0.37541(5) 0.8984(2) 0.71077(11) 0.0272(4) Uani 1 1 d . . . . .
F23 F 0.40836(5) 0.8412(2) 0.80917(11) 0.0309(5) Uani 1 1 d . . . . .
O21 O 0.34763(6) 0.6485(2) 0.69495(12) 0.0205(5) Uani 1 1 d . . . . .
O22 O 0.36807(6) 0.3690(2) 0.73015(12) 0.0216(5) Uani 1 1 d . . . . .
C21 C 0.37647(9) 0.8191(3) 0.77074(18) 0.0218(7) Uani 1 1 d . . . . .
C22 C 0.36984(8) 0.6665(3) 0.75073(17) 0.0192(7) Uani 1 1 d . . . . .
C23 C 0.38797(9) 0.5703(3) 0.79565(18) 0.0220(7) Uani 1 1 d . . . . .
H23 H 0.402715 0.603175 0.837430 0.026 Uiso 1 1 calc R U . . .
C24 C 0.38622(8) 0.4264(3) 0.78408(18) 0.0211(7) Uani 1 1 d D . . . .
C25A C 0.40722(9) 0.3346(3) 0.83593(17) 0.0212(7) Uani 0.504(4) 1 d D U P A 1
C26A C 0.4153(6) 0.2000(14) 0.8192(11) 0.027(2) Uani 0.504(4) 1 d D U P A 1
H26A H 0.407803 0.150983 0.775161 0.032 Uiso 0.504(4) 1 calc R U P A 1
C27A C 0.4406(5) 0.142(2) 0.8912(8) 0.024(2) Uani 0.504(4) 1 d D U P A 1
H27A H 0.450775 0.052596 0.897525 0.029 Uiso 0.504(4) 1 calc R U P A 1
C28A C 0.4440(6) 0.2482(13) 0.9398(11) 0.025(2) Uani 0.504(4) 1 d D U P A 1
H28A H 0.458493 0.238068 0.985274 0.030 Uiso 0.504(4) 1 calc R U P A 1
S21A S 0.42528(12) 0.3787(4) 0.92196(16) 0.0224(7) Uani 0.504(4) 1 d D U P A 1
C25B C 0.40722(9) 0.3346(3) 0.83593(17) 0.0212(7) Uani 0.496(4) 1 d D U P A 2
C26B C 0.4252(5) 0.3661(19) 0.9032(7) 0.027(2) Uani 0.496(4) 1 d D U P A 2
H26B H 0.426356 0.453344 0.927203 0.032 Uiso 0.496(4) 1 calc R U P A 2
C27B C 0.4445(6) 0.2200(14) 0.9336(11) 0.026(2) Uani 0.496(4) 1 d D U P A 2
H27B H 0.457957 0.203619 0.979744 0.031 Uiso 0.496(4) 1 calc R U P A 2
C28B C 0.4366(5) 0.1296(19) 0.8780(8) 0.023(2) Uani 0.496(4) 1 d D U P A 2
H28B H 0.446028 0.038586 0.881797 0.028 Uiso 0.496(4) 1 calc R U P A 2
S21B S 0.41312(15) 0.1708(4) 0.8104(3) 0.0281(8) Uani 0.496(4) 1 d D U P A 2
F31 F 0.40832(7) 0.0283(2) 0.57690(14) 0.0451(6) Uani 1 1 d . . . . .
F32 F 0.40850(7) 0.1141(3) 0.46853(14) 0.0478(6) Uani 1 1 d . . . . .
F33 F 0.45713(6) 0.1081(3) 0.54166(19) 0.0648(9) Uani 1 1 d . . . . .
O31 O 0.37860(6) 0.2841(2) 0.56801(12) 0.0227(5) Uani 1 1 d . . . . .
O32 O 0.40014(6) 0.5422(2) 0.61764(13) 0.0226(5) Uani 1 1 d . . . . .
C31 C 0.42204(10) 0.1301(4) 0.5388(3) 0.0371(10) Uani 1 1 d . . . . .
C32 C 0.41183(9) 0.2711(4) 0.56722(19) 0.0250(7) Uani 1 1 d . . . . .
C33 C 0.43836(10) 0.3661(4) 0.5848(2) 0.0326(9) Uani 1 1 d . . . . .
H33 H 0.462496 0.340269 0.581601 0.039 Uiso 1 1 calc R U . . .
C34 C 0.43075(9) 0.5015(4) 0.60770(19) 0.0235(7) Uani 1 1 d D . . . .
C35A C 0.46034(18) 0.6015(8) 0.6179(8) 0.0271(11) Uani 0.797(5) 1 d D U P B 1
C36A C 0.4968(4) 0.5860(14) 0.6121(6) 0.045(2) Uani 0.797(5) 1 d D U P B 1
H36A H 0.508345 0.499734 0.606969 0.054 Uiso 0.797(5) 1 calc R U P B 1
C37A C 0.51458(15) 0.7168(7) 0.6150(3) 0.0412(13) Uani 0.797(5) 1 d D U P B 1
H37A H 0.537059 0.734045 0.597440 0.049 Uiso 0.797(5) 1 calc R U P B 1
C38A C 0.49466(15) 0.8126(7) 0.6465(5) 0.0403(14) Uani 0.797(5) 1 d D U P B 1
H38A H 0.503540 0.900428 0.662844 0.048 Uiso 0.797(5) 1 calc R U P B 1
S31A S 0.45181(5) 0.75853(19) 0.65357(9) 0.0335(5) Uani 0.797(5) 1 d D U P B 1
C35B C 0.4577(7) 0.609(3) 0.623(3) 0.035(3) Uani 0.203(5) 1 d D U P B 2
C36B C 0.4518(6) 0.749(3) 0.635(2) 0.037(3) Uani 0.203(5) 1 d D U P B 2
H36B H 0.428874 0.790973 0.634147 0.044 Uiso 0.203(5) 1 calc R U P B 2
C37B C 0.4848(6) 0.822(2) 0.650(2) 0.040(3) Uani 0.203(5) 1 d D U P B 2
H37B H 0.487035 0.916081 0.664242 0.047 Uiso 0.203(5) 1 calc R U P B 2
C38B C 0.5127(5) 0.737(2) 0.6391(16) 0.045(3) Uani 0.203(5) 1 d D U P B 2
H38B H 0.536945 0.757363 0.655333 0.053 Uiso 0.203(5) 1 calc R U P B 2
S31B S 0.4985(4) 0.5883(14) 0.5928(6) 0.0416(18) Uani 0.203(5) 1 d D U P B 2
O41 O 0.28270(6) 0.5774(2) 0.60077(11) 0.0199(5) Uani 1 1 d . . . . .
O42 O 0.29048(6) 0.4546(2) 0.69997(12) 0.0202(5) Uani 1 1 d . . . . .
O43 O 0.24925(6) 0.6132(3) 0.68937(13) 0.0281(6) Uani 1 1 d . . . . .
N41 N 0.27336(7) 0.5504(3) 0.66456(14) 0.0180(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Four 
frame series were integrated and filtered for statistical outliers 
using SAINT (Bruker, 2016) then corrected for absorption by integration 
using SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale 
the combined data.  No decay correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.0480
1.00 0.00 -1.00 0.1230
-1.00 0.00 1.00 0.0950
2.00 1.00 0.00 0.0210
-2.00 -1.00 0.00 0.0460
2.00 2.00 -1.00 0.0330
1.00 2.00 0.00 0.0150
1.00 -1.00 0.00 0.0500
-2.00 0.00 -1.00 0.0840
1.00 0.00 0.00 0.0240
-1.00 0.00 0.00 0.0140

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
Eu1 O22 2.349(2) . ?
Eu1 O31 2.351(2) . ?
Eu1 O32 2.393(2) . ?
Eu1 O21 2.410(2) . ?
Eu1 O41 2.520(2) . ?
Eu1 N13 2.540(3) . ?
Eu1 N11 2.566(3) . ?
Eu1 O42 2.569(2) . ?
Eu1 N12 2.575(2) . ?
Eu1 N41 2.957(3) . ?
N11 C11 1.340(4) . ?
N11 C15 1.351(4) . ?
N12 C110 1.346(4) . ?
N12 C16 1.353(4) . ?
N13 C115 1.342(4) . ?
N13 C111 1.349(4) . ?
C11 C12 1.378(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.485(4) . ?
C16 C17 1.391(4) . ?
C17 C18 1.378(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(5) . ?
C18 H18 0.9500 . ?
C19 C110 1.396(4) . ?
C19 H19 0.9500 . ?
C110 C111 1.489(4) . ?
C111 C112 1.386(4) . ?
C112 C113 1.383(5) . ?
C112 H112 0.9500 . ?
C113 C114 1.379(5) . ?
C113 H113 0.9500 . ?
C114 C115 1.383(5) . ?
C114 H114 0.9500 . ?
C115 H115 0.9500 . ?
F21 C21 1.342(4) . ?
F22 C21 1.333(4) . ?
F23 C21 1.343(4) . ?
O21 C22 1.260(4) . ?
O22 C24 1.266(4) . ?
C21 C22 1.535(4) . ?
C22 C23 1.374(5) . ?
C23 C24 1.409(5) . ?
C23 H23 0.9500 . ?
C24 C25B 1.467(5) . ?
C24 C25A 1.467(5) . ?
C25A C26A 1.379(14) . ?
C25A S21A 1.699(4) . ?
C26A C27A 1.64(2) . ?
C26A H26A 0.9500 . ?
C27A C28A 1.352(11) . ?
C27A H27A 0.9500 . ?
C28A S21A 1.466(14) . ?
C28A H28A 0.9500 . ?
C25B C26B 1.372(13) . ?
C25B S21B 1.673(5) . ?
C26B C27B 1.66(2) . ?
C26B H26B 0.9500 . ?
C27B C28B 1.349(11) . ?
C27B H27B 0.9500 . ?
C28B S21B 1.494(13) . ?
C28B H28B 0.9500 . ?
F31 C31 1.338(5) . ?
F32 C31 1.339(5) . ?
F33 C31 1.333(4) . ?
O31 C32 1.259(4) . ?
O32 C34 1.248(4) . ?
C31 C32 1.522(5) . ?
C32 C33 1.371(5) . ?
C33 C34 1.413(5) . ?
C33 H33 0.9500 . ?
C34 C35B 1.462(9) . ?
C34 C35A 1.473(5) . ?
C35A C36A 1.396(13) . ?
C35A S31A 1.696(7) . ?
C36A C37A 1.429(14) . ?
C36A H36A 0.9500 . ?
C37A C38A 1.356(8) . ?
C37A H37A 0.9500 . ?
C38A S31A 1.713(6) . ?
C38A H38A 0.9500 . ?
C35B C36B 1.396(17) . ?
C35B S31B 1.695(13) . ?
C36B C37B 1.428(17) . ?
C36B H36B 0.9500 . ?
C37B C38B 1.360(11) . ?
C37B H37B 0.9500 . ?
C38B S31B 1.726(11) . ?
C38B H38B 0.9500 . ?
O41 N41 1.276(3) . ?
O42 N41 1.267(3) . ?
O43 N41 1.217(3) . ?

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
O22 Eu1 O31 83.60(8) . . ?
O22 Eu1 O32 78.38(8) . . ?
O31 Eu1 O32 70.83(8) . . ?
O22 Eu1 O21 74.04(7) . . ?
O31 Eu1 O21 137.60(7) . . ?
O32 Eu1 O21 69.66(8) . . ?
O22 Eu1 O41 123.40(7) . . ?
O31 Eu1 O41 147.51(7) . . ?
O32 Eu1 O41 127.74(8) . . ?
O21 Eu1 O41 72.61(7) . . ?
O22 Eu1 N13 150.14(8) . . ?
O31 Eu1 N13 96.62(8) . . ?
O32 Eu1 N13 73.61(8) . . ?
O21 Eu1 N13 86.58(8) . . ?
O41 Eu1 N13 69.30(8) . . ?
O22 Eu1 N11 81.59(8) . . ?
O31 Eu1 N11 71.71(8) . . ?
O32 Eu1 N11 139.04(8) . . ?
O21 Eu1 N11 136.83(8) . . ?
O41 Eu1 N11 93.07(8) . . ?
N13 Eu1 N11 126.98(8) . . ?
O22 Eu1 O42 75.94(7) . . ?
O31 Eu1 O42 138.35(7) . . ?
O32 Eu1 O42 136.73(7) . . ?
O21 Eu1 O42 70.11(7) . . ?
O41 Eu1 O42 50.18(7) . . ?
N13 Eu1 O42 118.92(8) . . ?
N11 Eu1 O42 69.70(7) . . ?
O22 Eu1 N12 142.22(8) . . ?
O31 Eu1 N12 72.91(8) . . ?
O32 Eu1 N12 118.97(8) . . ?
O21 Eu1 N12 141.91(7) . . ?
O41 Eu1 N12 74.61(7) . . ?
N13 Eu1 N12 63.83(8) . . ?
N11 Eu1 N12 63.31(8) . . ?
O42 Eu1 N12 102.48(7) . . ?
O22 Eu1 N41 98.58(8) . . ?
O31 Eu1 N41 154.87(7) . . ?
O32 Eu1 N41 134.23(7) . . ?
O21 Eu1 N41 65.77(7) . . ?
O41 Eu1 N41 25.38(7) . . ?
N13 Eu1 N41 93.65(8) . . ?
N11 Eu1 N41 83.79(8) . . ?
O42 Eu1 N41 25.27(7) . . ?
N12 Eu1 N41 91.41(7) . . ?
C11 N11 C15 117.7(3) . . ?
C11 N11 Eu1 120.4(2) . . ?
C15 N11 Eu1 121.67(19) . . ?
C110 N12 C16 118.5(3) . . ?
C110 N12 Eu1 120.36(19) . . ?
C16 N12 Eu1 120.64(19) . . ?
C115 N13 C111 118.0(3) . . ?
C115 N13 Eu1 119.6(2) . . ?
C111 N13 Eu1 121.7(2) . . ?
N11 C11 C12 123.4(3) . . ?
N11 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C13 C12 C11 118.8(3) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 118.7(3) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
N11 C15 C14 121.8(3) . . ?
N11 C15 C16 116.2(3) . . ?
C14 C15 C16 122.0(3) . . ?
N12 C16 C17 121.5(3) . . ?
N12 C16 C15 117.1(3) . . ?
C17 C16 C15 121.3(3) . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 118.9(3) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C18 C19 C110 119.0(3) . . ?
C18 C19 H19 120.5 . . ?
C110 C19 H19 120.5 . . ?
N12 C110 C19 122.2(3) . . ?
N12 C110 C111 116.8(3) . . ?
C19 C110 C111 121.0(3) . . ?
N13 C111 C112 121.9(3) . . ?
N13 C111 C110 116.3(3) . . ?
C112 C111 C110 121.7(3) . . ?
C113 C112 C111 119.1(3) . . ?
C113 C112 H112 120.4 . . ?
C111 C112 H112 120.4 . . ?
C114 C113 C112 119.4(3) . . ?
C114 C113 H113 120.3 . . ?
C112 C113 H113 120.3 . . ?
C113 C114 C115 118.3(3) . . ?
C113 C114 H114 120.8 . . ?
C115 C114 H114 120.8 . . ?
N13 C115 C114 123.2(3) . . ?
N13 C115 H115 118.4 . . ?
C114 C115 H115 118.4 . . ?
C22 O21 Eu1 127.6(2) . . ?
C24 O22 Eu1 133.9(2) . . ?
F22 C21 F21 107.2(3) . . ?
F22 C21 F23 106.6(3) . . ?
F21 C21 F23 106.5(3) . . ?
F22 C21 C22 111.6(3) . . ?
F21 C21 C22 111.5(3) . . ?
F23 C21 C22 113.1(3) . . ?
O21 C22 C23 129.4(3) . . ?
O21 C22 C21 113.7(3) . . ?
C23 C22 C21 116.8(3) . . ?
C22 C23 C24 124.6(3) . . ?
C22 C23 H23 117.7 . . ?
C24 C23 H23 117.7 . . ?
O22 C24 C23 124.2(3) . . ?
O22 C24 C25B 116.5(3) . . ?
C23 C24 C25B 119.2(3) . . ?
O22 C24 C25A 116.5(3) . . ?
C23 C24 C25A 119.2(3) . . ?
C26A C25A C24 123.1(8) . . ?
C26A C25A S21A 111.4(8) . . ?
C24 C25A S21A 125.5(3) . . ?
C25A C26A C27A 105.6(11) . . ?
C25A C26A H26A 127.2 . . ?
C27A C26A H26A 127.2 . . ?
C28A C27A C26A 105.9(16) . . ?
C28A C27A H27A 127.0 . . ?
C26A C27A H27A 127.0 . . ?
C27A C28A S21A 119.8(17) . . ?
C27A C28A H28A 120.1 . . ?
S21A C28A H28A 120.1 . . ?
C28A S21A C25A 97.2(7) . . ?
C26B C25B C24 128.6(8) . . ?
C26B C25B S21B 113.1(7) . . ?
C24 C25B S21B 118.2(3) . . ?
C25B C26B C27B 105.6(11) . . ?
C25B C26B H26B 127.2 . . ?
C27B C26B H26B 127.2 . . ?
C28B C27B C26B 104.2(16) . . ?
C28B C27B H27B 127.9 . . ?
C26B C27B H27B 127.9 . . ?
C27B C28B S21B 120.9(17) . . ?
C27B C28B H28B 119.6 . . ?
S21B C28B H28B 119.6 . . ?
C28B S21B C25B 96.1(7) . . ?
C32 O31 Eu1 134.9(2) . . ?
C34 O32 Eu1 138.3(2) . . ?
F33 C31 F31 107.2(3) . . ?
F33 C31 F32 107.2(4) . . ?
F31 C31 F32 106.4(3) . . ?
F33 C31 C32 114.4(3) . . ?
F31 C31 C32 111.0(3) . . ?
F32 C31 C32 110.1(3) . . ?
O31 C32 C33 129.1(3) . . ?
O31 C32 C31 112.3(3) . . ?
C33 C32 C31 118.5(3) . . ?
C32 C33 C34 121.8(3) . . ?
C32 C33 H33 119.1 . . ?
C34 C33 H33 119.1 . . ?
O32 C34 C33 123.6(3) . . ?
O32 C34 C35B 112.4(11) . . ?
C33 C34 C35B 124.0(11) . . ?
O32 C34 C35A 118.2(4) . . ?
C33 C34 C35A 118.2(4) . . ?
C36A C35A C34 131.0(7) . . ?
C36A C35A S31A 110.6(6) . . ?
C34 C35A S31A 117.8(5) . . ?
C35A C36A C37A 111.2(9) . . ?
C35A C36A H36A 124.4 . . ?
C37A C36A H36A 124.4 . . ?
C38A C37A C36A 110.1(7) . . ?
C38A C37A H37A 124.9 . . ?
C36A C37A H37A 124.9 . . ?
C37A C38A S31A 112.9(5) . . ?
C37A C38A H38A 123.6 . . ?
S31A C38A H38A 123.6 . . ?
C35A S31A C38A 91.6(3) . . ?
C36B C35B C34 127(2) . . ?
C36B C35B S31B 109.5(13) . . ?
C34 C35B S31B 119.2(14) . . ?
C35B C36B C37B 110.8(14) . . ?
C35B C36B H36B 124.6 . . ?
C37B C36B H36B 124.6 . . ?
C38B C37B C36B 110.3(13) . . ?
C38B C37B H37B 124.8 . . ?
C36B C37B H37B 124.8 . . ?
C37B C38B S31B 111.6(12) . . ?
C37B C38B H38B 124.2 . . ?
S31B C38B H38B 124.2 . . ?
C35B S31B C38B 89.2(8) . . ?
N41 O41 Eu1 96.80(17) . . ?
N41 O42 Eu1 94.75(16) . . ?
O43 N41 O42 122.3(3) . . ?
O43 N41 O41 121.5(3) . . ?
O42 N41 O41 116.2(2) . . ?
O43 N41 Eu1 167.8(2) . . ?
O42 N41 Eu1 59.97(14) . . ?
O41 N41 Eu1 57.82(14) . . ?

_refine_diff_density_max         1.444
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.093




_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_pbar1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1913269'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2019-04-30 deposited with the CCDC.	2021-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H19 Bi Cl F6 N3 O4 S2'
_chemical_formula_sum            'C31 H19 Bi Cl F6 N3 O4 S2'
_chemical_formula_weight         920.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.3216(5)
_cell_length_b                   10.7535(5)
_cell_length_c                   14.8647(7)
_cell_angle_alpha                91.665(2)
_cell_angle_beta                 91.689(2)
_cell_angle_gamma                109.018(2)
_cell_volume                     1557.84(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9838
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      26.43

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.133
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    5.958
_shelx_estimated_absorpt_T_min   0.505
_shelx_estimated_absorpt_T_max   0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6544
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50035
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.089
_diffrn_reflns_theta_max         26.449
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6421
_reflns_number_gt                5864
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/4 (Bruker, 2014) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXle (Sheldrick, 2011)'
_computing_publication_material  'enCIFer V1.6.1. (IUCr, 2017)'
_refine_special_details          
;Structure was phased by direct methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F². A final analysis of variance between observed 
and calculated structure factors showed some dependence on amplitude 
and little dependence on resolution.,Disorder on both thiophene groups
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0154P)²+1.4653P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6421
_refine_ls_number_parameters     507
_refine_ls_number_restraints     256
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0393
_refine_ls_wR_factor_gt          0.0381
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.69650(2) 0.79187(2) 0.30911(2) 0.01197(4) Uani 1 1 d . . . . .
Cl1 Cl 0.46885(7) 0.78766(7) 0.37952(5) 0.02028(15) Uani 1 1 d . . . . .
C11 C 1.0337(3) 0.5813(3) 0.2213(2) 0.0293(8) Uani 1 1 d . . . . .
C12 C 0.9796(3) 0.6966(3) 0.23325(19) 0.0192(6) Uani 1 1 d . . . . .
C13 C 1.0414(3) 0.8066(3) 0.18441(19) 0.0189(6) Uani 1 1 d . . . . .
H13 H 1.111076 0.803404 0.144889 0.023 Uiso 1 1 calc R U . . .
C14 C 1.0069(3) 0.9228(3) 0.19006(18) 0.0166(6) Uani 1 1 d . . . . .
C15 C 1.0705(3) 1.0299(3) 0.12998(18) 0.0193(6) Uani 1 1 d D . . . .
C16A C 1.1581(18) 1.028(2) 0.0603(12) 0.022(3) Uani 0.626(4) 1 d D U P A 1
H16A H 1.191925 0.958171 0.046058 0.026 Uiso 0.626(4) 1 calc R U P A 1
C17A C 1.1895(12) 1.1507(7) 0.0129(8) 0.0244(16) Uani 0.626(4) 1 d D U P A 1
H17A H 1.248687 1.170667 -0.036179 0.029 Uiso 0.626(4) 1 calc R U P A 1
C18A C 1.1256(10) 1.2333(10) 0.0461(5) 0.0239(18) Uani 0.626(4) 1 d D U P A 1
H18A H 1.134202 1.316965 0.023057 0.029 Uiso 0.626(4) 1 calc R U P A 1
S11A S 1.0275(4) 1.1676(3) 0.1349(3) 0.0221(5) Uani 0.626(4) 1 d D U P A 1
C16B C 1.036(3) 1.1458(18) 0.1370(18) 0.025(4) Uani 0.374(4) 1 d D U P A 2
H16B H 0.977225 1.163540 0.179976 0.030 Uiso 0.374(4) 1 calc R U P A 2
C17B C 1.1048(17) 1.2344(17) 0.0679(9) 0.022(2) Uani 0.374(4) 1 d D U P A 2
H17B H 1.093836 1.317586 0.059105 0.027 Uiso 0.374(4) 1 calc R U P A 2
C18B C 1.1859(19) 1.1858(11) 0.0174(13) 0.022(2) Uani 0.374(4) 1 d D U P A 2
H18B H 1.239637 1.231179 -0.029700 0.026 Uiso 0.374(4) 1 calc R U P A 2
S11B S 1.1792(8) 1.0326(9) 0.0494(5) 0.0217(10) Uani 0.374(4) 1 d D U P A 2
O11 O 0.8819(2) 0.6743(2) 0.28537(14) 0.0263(5) Uani 1 1 d . . . . .
O12 O 0.9247(2) 0.94319(19) 0.24533(13) 0.0201(4) Uani 1 1 d . . . . .
F11 F 0.9607(3) 0.4944(2) 0.15796(15) 0.0527(6) Uani 1 1 d . . . . .
F12 F 1.0227(2) 0.51300(19) 0.29664(14) 0.0421(5) Uani 1 1 d . . . . .
F13 F 1.1635(2) 0.6143(2) 0.2005(2) 0.0661(8) Uani 1 1 d . . . . .
C21 C 0.4068(3) 0.6324(3) 0.0561(2) 0.0262(7) Uani 1 1 d . . . . .
C22 C 0.4821(3) 0.6133(3) 0.14177(18) 0.0175(6) Uani 1 1 d . . . . .
C23 C 0.4366(3) 0.4952(3) 0.18238(19) 0.0179(6) Uani 1 1 d . . . . .
H23 H 0.359531 0.428240 0.155447 0.022 Uiso 1 1 calc R U . . .
C24 C 0.4982(3) 0.4672(3) 0.26279(18) 0.0137(6) Uani 1 1 d . . . . .
C25 C 0.4604(3) 0.3299(3) 0.28934(18) 0.0143(6) Uani 1 1 d D . . . .
C26A C 0.3958(8) 0.2177(6) 0.2404(4) 0.0183(9) Uani 0.932(3) 1 d D U P B 1
H26A H 0.358993 0.216227 0.180888 0.022 Uiso 0.932(3) 1 calc R U P B 1
C27A C 0.3883(6) 0.1014(3) 0.2870(2) 0.0184(7) Uani 0.932(3) 1 d D U P B 1
H27A H 0.347298 0.014401 0.262289 0.022 Uiso 0.932(3) 1 calc R U P B 1
C28A C 0.4477(4) 0.1316(3) 0.3719(2) 0.0168(8) Uani 0.932(3) 1 d D U P B 1
H28A H 0.453038 0.067520 0.413195 0.020 Uiso 0.932(3) 1 calc R U P B 1
S21A S 0.51139(9) 0.29806(8) 0.39506(5) 0.0150(3) Uani 0.932(3) 1 d D U P B 1
C26B C 0.516(6) 0.309(3) 0.367(2) 0.017(4) Uani 0.068(3) 1 d D U P B 2
H26B H 0.582692 0.373155 0.404576 0.021 Uiso 0.068(3) 1 calc R U P B 2
C27B C 0.460(6) 0.172(3) 0.385(2) 0.016(3) Uani 0.068(3) 1 d D U P B 2
H27B H 0.463285 0.136449 0.442224 0.019 Uiso 0.068(3) 1 calc R U P B 2
C28B C 0.400(9) 0.100(2) 0.309(3) 0.017(3) Uani 0.068(3) 1 d D U P B 2
H28B H 0.372667 0.006345 0.303835 0.020 Uiso 0.068(3) 1 calc R U P B 2
S21B S 0.378(3) 0.1950(17) 0.2227(14) 0.019(3) Uani 0.068(3) 1 d D U P B 2
O21 O 0.5837(2) 0.71639(18) 0.16314(12) 0.0202(4) Uani 1 1 d . . . . .
O22 O 0.58364(19) 0.55202(18) 0.31355(12) 0.0170(4) Uani 1 1 d . . . . .
F21 F 0.4913(2) 0.6664(2) -0.01160(11) 0.0376(5) Uani 1 1 d . . . . .
F22 F 0.3558(2) 0.7315(2) 0.06831(13) 0.0397(5) Uani 1 1 d . . . . .
F23 F 0.3027(2) 0.5279(2) 0.02706(14) 0.0549(7) Uani 1 1 d . . . . .
N31 N 0.7733(2) 0.7451(2) 0.46237(15) 0.0147(5) Uani 1 1 d . . . . .
N32 N 0.7861(2) 0.9909(2) 0.41573(14) 0.0111(5) Uani 1 1 d . . . . .
N33 N 0.6791(2) 1.0030(2) 0.24762(15) 0.0160(5) Uani 1 1 d . . . . .
C31 C 0.7618(3) 0.6221(3) 0.48264(19) 0.0190(6) Uani 1 1 d . . . . .
H31 H 0.729894 0.554458 0.436899 0.023 Uiso 1 1 calc R U . . .
C32 C 0.7945(3) 0.5891(3) 0.56736(19) 0.0200(6) Uani 1 1 d . . . . .
H32 H 0.781801 0.500159 0.580612 0.024 Uiso 1 1 calc R U . . .
C33 C 0.8459(3) 0.6885(3) 0.63201(19) 0.0178(6) Uani 1 1 d . . . . .
H33 H 0.870050 0.668838 0.690784 0.021 Uiso 1 1 calc R U . . .
C34 C 0.8623(3) 0.8169(3) 0.61147(18) 0.0154(6) Uani 1 1 d . . . . .
H34 H 0.900655 0.886582 0.655136 0.019 Uiso 1 1 calc R U . . .
C35 C 0.8219(3) 0.8429(3) 0.52578(18) 0.0131(6) Uani 1 1 d . . . . .
C36 C 0.8280(3) 0.9778(3) 0.50062(18) 0.0130(6) Uani 1 1 d . . . . .
C37 C 0.8725(3) 1.0852(3) 0.56158(18) 0.0166(6) Uani 1 1 d . . . . .
H37 H 0.904311 1.075218 0.620677 0.020 Uiso 1 1 calc R U . . .
C38 C 0.8699(3) 1.2062(3) 0.53530(19) 0.0185(6) Uani 1 1 d . . . . .
H38 H 0.898424 1.280186 0.576429 0.022 Uiso 1 1 calc R U . . .
C39 C 0.8254(3) 1.2188(3) 0.44861(19) 0.0167(6) Uani 1 1 d . . . . .
H39 H 0.822412 1.301409 0.429620 0.020 Uiso 1 1 calc R U . . .
C310 C 0.7850(3) 1.1092(3) 0.38929(18) 0.0130(6) Uani 1 1 d . . . . .
C311 C 0.7371(3) 1.1177(3) 0.29500(18) 0.0145(6) Uani 1 1 d . . . . .
C312 C 0.7509(3) 1.2376(3) 0.25689(19) 0.0187(6) Uani 1 1 d . . . . .
H312 H 0.794134 1.317720 0.290516 0.022 Uiso 1 1 calc R U . . .
C313 C 0.7013(3) 1.2395(3) 0.16977(19) 0.0210(7) Uani 1 1 d . . . . .
H313 H 0.709626 1.320628 0.142825 0.025 Uiso 1 1 calc R U . . .
C314 C 0.6396(3) 1.1215(3) 0.1226(2) 0.0237(7) Uani 1 1 d . . . . .
H314 H 0.603307 1.119985 0.062921 0.028 Uiso 1 1 calc R U . . .
C315 C 0.6314(3) 1.0060(3) 0.16332(19) 0.0213(7) Uani 1 1 d . . . . .
H315 H 0.590113 0.925097 0.130194 0.026 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 O21 2.4196(18) . ?
Bi1 O22 2.4638(18) . ?
Bi1 N31 2.508(2) . ?
Bi1 N32 2.525(2) . ?
Bi1 N33 2.529(2) . ?
Bi1 Cl1 2.5879(7) . ?
Bi1 O12 2.6111(19) . ?
Bi1 O11 2.641(2) . ?
C11 F13 1.318(4) . ?
C11 F11 1.333(4) . ?
C11 F12 1.344(4) . ?
C11 C12 1.525(4) . ?
C12 O11 1.254(3) . ?
C12 C13 1.385(4) . ?
C13 C14 1.408(4) . ?
C13 H13 0.9500 . ?
C14 O12 1.263(3) . ?
C14 C15 1.469(4) . ?
C15 C16A 1.398(14) . ?
C15 C16B 1.405(15) . ?
C15 S11B 1.659(6) . ?
C15 S11A 1.679(4) . ?
C16A C17A 1.457(18) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.358(8) . ?
C17A H17A 0.9500 . ?
C18A S11A 1.713(7) . ?
C18A H18A 0.9500 . ?
C16B C17B 1.46(2) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.354(9) . ?
C17B H17B 0.9500 . ?
C18B S11B 1.709(11) . ?
C18B H18B 0.9500 . ?
C21 F23 1.328(3) . ?
C21 F21 1.332(4) . ?
C21 F22 1.343(4) . ?
C21 C22 1.526(4) . ?
C22 O21 1.278(3) . ?
C22 C23 1.367(4) . ?
C23 C24 1.423(4) . ?
C23 H23 0.9500 . ?
C24 O22 1.255(3) . ?
C24 C25 1.468(4) . ?
C25 C26B 1.340(11) . ?
C25 C26A 1.352(6) . ?
C25 S21B 1.694(10) . ?
C25 S21A 1.722(3) . ?
C26A C27A 1.428(6) . ?
C26A H26A 0.9500 . ?
C27A C28A 1.369(4) . ?
C27A H27A 0.9500 . ?
C28A S21A 1.715(3) . ?
C28A H28A 0.9500 . ?
C26B C27B 1.425(12) . ?
C26B H26B 0.9500 . ?
C27B C28B 1.367(11) . ?
C27B H27B 0.9500 . ?
C28B S21B 1.715(11) . ?
C28B H28B 0.9500 . ?
N31 C31 1.333(4) . ?
N31 C35 1.348(3) . ?
N32 C310 1.345(3) . ?
N32 C36 1.348(3) . ?
N33 C315 1.338(4) . ?
N33 C311 1.349(3) . ?
C31 C32 1.380(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.374(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.380(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.393(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.490(4) . ?
C36 C37 1.391(4) . ?
C37 C38 1.377(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.380(4) . ?
C38 H38 0.9500 . ?
C39 C310 1.392(4) . ?
C39 H39 0.9500 . ?
C310 C311 1.488(4) . ?
C311 C312 1.390(4) . ?
C312 C313 1.382(4) . ?
C312 H312 0.9500 . ?
C313 C314 1.379(4) . ?
C313 H313 0.9500 . ?
C314 C315 1.376(4) . ?
C314 H314 0.9500 . ?
C315 H315 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
O21 Bi1 O22 72.56(6) . . ?
O21 Bi1 N31 150.61(7) . . ?
O22 Bi1 N31 78.36(7) . . ?
O21 Bi1 N32 143.49(7) . . ?
O22 Bi1 N32 139.58(6) . . ?
N31 Bi1 N32 65.27(7) . . ?
O21 Bi1 N33 78.29(7) . . ?
O22 Bi1 N33 144.91(7) . . ?
N31 Bi1 N33 130.40(7) . . ?
N32 Bi1 N33 65.28(7) . . ?
O21 Bi1 Cl1 92.11(5) . . ?
O22 Bi1 Cl1 80.52(5) . . ?
N31 Bi1 Cl1 87.14(5) . . ?
N32 Bi1 Cl1 80.66(5) . . ?
N33 Bi1 Cl1 81.48(5) . . ?
O21 Bi1 O12 95.15(6) . . ?
O22 Bi1 O12 134.60(6) . . ?
N31 Bi1 O12 102.37(7) . . ?
N32 Bi1 O12 73.03(6) . . ?
N33 Bi1 O12 66.30(7) . . ?
Cl1 Bi1 O12 144.61(5) . . ?
O21 Bi1 O11 93.47(7) . . ?
O22 Bi1 O11 71.20(6) . . ?
N31 Bi1 O11 72.92(7) . . ?
N32 Bi1 O11 111.55(7) . . ?
N33 Bi1 O11 130.53(7) . . ?
Cl1 Bi1 O11 147.96(5) . . ?
O12 Bi1 O11 66.04(6) . . ?
F13 C11 F11 107.3(3) . . ?
F13 C11 F12 106.0(3) . . ?
F11 C11 F12 105.1(3) . . ?
F13 C11 C12 114.8(3) . . ?
F11 C11 C12 111.4(3) . . ?
F12 C11 C12 111.5(3) . . ?
O11 C12 C13 130.1(3) . . ?
O11 C12 C11 113.4(3) . . ?
C13 C12 C11 116.5(3) . . ?
C12 C13 C14 123.7(3) . . ?
C12 C13 H13 118.2 . . ?
C14 C13 H13 118.2 . . ?
O12 C14 C13 124.1(3) . . ?
O12 C14 C15 116.5(2) . . ?
C13 C14 C15 119.4(3) . . ?
C16A C15 C14 127.2(9) . . ?
C16B C15 C14 118.7(9) . . ?
C16B C15 S11B 113.1(7) . . ?
C14 C15 S11B 128.2(4) . . ?
C16A C15 S11A 112.9(8) . . ?
C14 C15 S11A 119.7(2) . . ?
C15 C16A C17A 109.6(15) . . ?
C15 C16A H16A 125.2 . . ?
C17A C16A H16A 125.2 . . ?
C18A C17A C16A 113.2(12) . . ?
C18A C17A H17A 123.4 . . ?
C16A C17A H17A 123.4 . . ?
C17A C18A S11A 111.4(9) . . ?
C17A C18A H18A 124.3 . . ?
S11A C18A H18A 124.3 . . ?
C15 S11A C18A 93.0(5) . . ?
C15 C16B C17B 109.1(16) . . ?
C15 C16B H16B 125.5 . . ?
C17B C16B H16B 125.5 . . ?
C18B C17B C16B 113.1(17) . . ?
C18B C17B H17B 123.4 . . ?
C16B C17B H17B 123.4 . . ?
C17B C18B S11B 111.3(15) . . ?
C17B C18B H18B 124.3 . . ?
S11B C18B H18B 124.3 . . ?
C15 S11B C18B 93.4(8) . . ?
C12 O11 Bi1 131.47(18) . . ?
C14 O12 Bi1 133.07(17) . . ?
F23 C21 F21 106.9(3) . . ?
F23 C21 F22 106.7(3) . . ?
F21 C21 F22 105.7(2) . . ?
F23 C21 C22 114.9(2) . . ?
F21 C21 C22 111.4(3) . . ?
F22 C21 C22 110.8(2) . . ?
O21 C22 C23 130.2(3) . . ?
O21 C22 C21 110.9(2) . . ?
C23 C22 C21 118.9(3) . . ?
C22 C23 C24 123.6(3) . . ?
C22 C23 H23 118.2 . . ?
C24 C23 H23 118.2 . . ?
O22 C24 C23 124.7(2) . . ?
O22 C24 C25 116.8(2) . . ?
C23 C24 C25 118.5(2) . . ?
C26B C25 C24 116.6(14) . . ?
C26A C25 C24 129.5(3) . . ?
C26B C25 S21B 116.3(13) . . ?
C24 C25 S21B 126.0(8) . . ?
C26A C25 S21A 111.6(3) . . ?
C24 C25 S21A 118.7(2) . . ?
C25 C26A C27A 113.3(4) . . ?
C25 C26A H26A 123.3 . . ?
C27A C26A H26A 123.3 . . ?
C28A C27A C26A 111.3(3) . . ?
C28A C27A H27A 124.4 . . ?
C26A C27A H27A 124.4 . . ?
C27A C28A S21A 112.3(3) . . ?
C27A C28A H28A 123.8 . . ?
S21A C28A H28A 123.8 . . ?
C28A S21A C25 91.43(15) . . ?
C25 C26B C27B 108.3(17) . . ?
C25 C26B H26B 125.8 . . ?
C27B C26B H26B 125.8 . . ?
C28B C27B C26B 111.3(14) . . ?
C28B C27B H27B 124.3 . . ?
C26B C27B H27B 124.3 . . ?
C27B C28B S21B 112.8(13) . . ?
C27B C28B H28B 123.6 . . ?
S21B C28B H28B 123.6 . . ?
C25 S21B C28B 88.4(10) . . ?
C22 O21 Bi1 129.27(17) . . ?
C24 O22 Bi1 134.38(17) . . ?
C31 N31 C35 119.4(2) . . ?
C31 N31 Bi1 120.02(18) . . ?
C35 N31 Bi1 120.51(17) . . ?
C310 N32 C36 119.9(2) . . ?
C310 N32 Bi1 119.86(17) . . ?
C36 N32 Bi1 120.18(17) . . ?
C315 N33 C311 118.8(2) . . ?
C315 N33 Bi1 120.91(18) . . ?
C311 N33 Bi1 119.59(17) . . ?
N31 C31 C32 122.7(3) . . ?
N31 C31 H31 118.7 . . ?
C32 C31 H31 118.7 . . ?
C33 C32 C31 118.2(3) . . ?
C33 C32 H32 120.9 . . ?
C31 C32 H32 120.9 . . ?
C32 C33 C34 119.9(3) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C34 C35 119.0(3) . . ?
C33 C34 H34 120.5 . . ?
C35 C34 H34 120.5 . . ?
N31 C35 C34 120.7(2) . . ?
N31 C35 C36 117.3(2) . . ?
C34 C35 C36 122.1(2) . . ?
N32 C36 C37 121.1(2) . . ?
N32 C36 C35 116.7(2) . . ?
C37 C36 C35 122.1(2) . . ?
C38 C37 C36 119.3(3) . . ?
C38 C37 H37 120.4 . . ?
C36 C37 H37 120.4 . . ?
C37 C38 C39 119.3(3) . . ?
C37 C38 H38 120.3 . . ?
C39 C38 H38 120.3 . . ?
C38 C39 C310 119.3(3) . . ?
C38 C39 H39 120.3 . . ?
C310 C39 H39 120.3 . . ?
N32 C310 C39 121.0(2) . . ?
N32 C310 C311 117.5(2) . . ?
C39 C310 C311 121.5(2) . . ?
N33 C311 C312 121.1(2) . . ?
N33 C311 C310 116.8(2) . . ?
C312 C311 C310 122.0(2) . . ?
C313 C312 C311 119.5(3) . . ?
C313 C312 H312 120.2 . . ?
C311 C312 H312 120.2 . . ?
C314 C313 C312 118.8(3) . . ?
C314 C313 H313 120.6 . . ?
C312 C313 H313 120.6 . . ?
C315 C314 C313 118.9(3) . . ?
C315 C314 H314 120.5 . . ?
C313 C314 H314 120.5 . . ?
N33 C315 C314 122.8(3) . . ?
N33 C315 H315 118.6 . . ?
C314 C315 H315 118.6 . . ?

_refine_diff_density_max         0.975
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.098



_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_c2onc_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1913268'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2019-04-30 deposited with the CCDC.	2021-10-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H15 Bi Br2 F3 N3 O2 S'
_chemical_formula_sum            'C23 H15 Bi Br2 F3 N3 O2 S'
_chemical_formula_weight         823.24

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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   30.2542(14)
_cell_length_b                   8.7876(4)
_cell_length_c                   18.6371(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.0510(10)
_cell_angle_gamma                90
_cell_volume                     4927.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9862
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      26.43

_exptl_crystal_description       'thick needles'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.220
_exptl_crystal_F_000             3088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.073
_exptl_absorpt_coefficient_mu    10.535
_shelx_estimated_absorpt_T_min   0.213
_shelx_estimated_absorpt_T_max   0.513
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2786
_exptl_absorpt_correction_T_max  0.6162
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37438
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.415
_diffrn_reflns_theta_max         26.429
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5047
_reflns_number_gt                4594
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 V2014.9-0 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.34A, XPREP v2014/2, SADABS V2014/4 (Bruker, 2014) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXle (Sheldrick, 2011)'
_computing_publication_material  'enCIFer V1.6.1. (IUCr, 2017)'
_refine_special_details          
; 
Structure was phased by direct methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F². A final analysis of variance between observed 
and calculated structure factors showed some dependence on amplitude 
and little dependence on resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0173P)²+7.0542P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5047
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0185
_refine_ls_wR_factor_ref         0.0425
_refine_ls_wR_factor_gt          0.0412
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.38141(2) 0.76494(2) 0.54613(2) 0.01533(4) Uani 1 1 d . . . . .
Br1 Br 0.40210(2) 0.99199(4) 0.64579(2) 0.02875(8) Uani 1 1 d . . . . .
Br2 Br 0.35619(2) 0.55354(3) 0.42868(2) 0.02191(7) Uani 1 1 d . . . . .
N11 N 0.46265(8) 0.7428(3) 0.52765(13) 0.0177(5) Uani 1 1 d . . . . .
N12 N 0.40557(8) 0.9334(3) 0.44858(12) 0.0171(5) Uani 1 1 d . . . . .
N13 N 0.32280(8) 0.9462(3) 0.49086(12) 0.0187(5) Uani 1 1 d . . . . .
C11 C 0.49051(9) 0.6522(3) 0.56902(15) 0.0209(6) Uani 1 1 d . . . . .
H11 H 0.480040 0.605086 0.609889 0.025 Uiso 1 1 calc R U . . .
C12 C 0.53373(9) 0.6243(3) 0.55494(16) 0.0217(6) Uani 1 1 d . . . . .
H12 H 0.552637 0.559988 0.585545 0.026 Uiso 1 1 calc R U . . .
C13 C 0.54872(10) 0.6923(4) 0.49520(16) 0.0236(7) Uani 1 1 d . . . . .
H13 H 0.578053 0.673774 0.483494 0.028 Uiso 1 1 calc R U . . .
C14 C 0.52077(10) 0.7869(3) 0.45286(17) 0.0233(7) Uani 1 1 d . . . . .
H14 H 0.530856 0.835214 0.411981 0.028 Uiso 1 1 calc R U . . .
C15 C 0.47761(9) 0.8121(3) 0.46996(15) 0.0185(6) Uani 1 1 d . . . . .
C16 C 0.44679(9) 0.9165(3) 0.42744(15) 0.0190(6) Uani 1 1 d . . . . .
C17 C 0.45962(10) 0.9973(4) 0.36840(16) 0.0244(7) Uani 1 1 d . . . . .
H17 H 0.488594 0.985014 0.353927 0.029 Uiso 1 1 calc R U . . .
C18 C 0.42986(10) 1.0942(4) 0.33176(16) 0.0260(7) Uani 1 1 d . . . . .
H18 H 0.438173 1.149524 0.291482 0.031 Uiso 1 1 calc R U . . .
C19 C 0.38800(10) 1.1120(4) 0.35296(16) 0.0247(7) Uani 1 1 d . . . . .
H19 H 0.367214 1.179051 0.327632 0.030 Uiso 1 1 calc R U . . .
C110 C 0.37663(9) 1.0299(3) 0.41233(15) 0.0190(6) Uani 1 1 d . . . . .
C111 C 0.33144(10) 1.0395(3) 0.43713(15) 0.0194(6) Uani 1 1 d . . . . .
C112 C 0.29911(10) 1.1374(3) 0.40494(17) 0.0248(7) Uani 1 1 d . . . . .
H112 H 0.306019 1.205534 0.368171 0.030 Uiso 1 1 calc R U . . .
C113 C 0.25708(10) 1.1349(4) 0.42663(17) 0.0265(7) Uani 1 1 d . . . . .
H113 H 0.234526 1.199370 0.404144 0.032 Uiso 1 1 calc R U . . .
C114 C 0.24798(10) 1.0380(3) 0.48123(16) 0.0229(7) Uani 1 1 d . . . . .
H114 H 0.219179 1.034651 0.497153 0.027 Uiso 1 1 calc R U . . .
C115 C 0.28171(10) 0.9459(3) 0.51232(16) 0.0220(7) Uani 1 1 d . . . . .
H115 H 0.275653 0.879640 0.550365 0.026 Uiso 1 1 calc R U . . .
S21 S 0.23134(2) 0.72190(9) 0.65825(4) 0.02210(16) Uani 1 1 d . . . . .
F21 F 0.45584(6) 0.5306(2) 0.77728(10) 0.0400(5) Uani 1 1 d . . . . .
F22 F 0.45477(5) 0.3537(2) 0.69817(9) 0.0258(4) Uani 1 1 d . . . . .
F23 F 0.41236(6) 0.3391(3) 0.78272(11) 0.0429(6) Uani 1 1 d . . . . .
O21 O 0.40790(6) 0.5700(3) 0.63156(11) 0.0267(5) Uani 1 1 d . . . . .
O22 O 0.32016(6) 0.6997(2) 0.61796(11) 0.0202(4) Uani 1 1 d . . . . .
C21 C 0.42909(9) 0.4350(3) 0.73703(16) 0.0209(6) Uani 1 1 d . . . . .
C22 C 0.39394(9) 0.5265(3) 0.69000(15) 0.0178(6) Uani 1 1 d . . . . .
C23 C 0.35390(9) 0.5515(3) 0.71612(15) 0.0172(6) Uani 1 1 d . . . . .
H23 H 0.349710 0.512152 0.762396 0.021 Uiso 1 1 calc R U . . .
C24 C 0.31815(9) 0.6333(3) 0.67778(15) 0.0166(6) Uani 1 1 d . . . . .
C25 C 0.27545(9) 0.6375(3) 0.70822(15) 0.0166(6) Uani 1 1 d . . . . .
C26 C 0.26255(8) 0.5753(3) 0.77229(14) 0.0147(6) Uani 1 1 d . . . . .
H26 H 0.281973 0.522634 0.807209 0.018 Uiso 1 1 calc R U . . .
C27 C 0.21733(10) 0.6011(4) 0.77803(17) 0.0251(7) Uani 1 1 d . . . . .
H27 H 0.202704 0.568383 0.817982 0.030 Uiso 1 1 calc R U . . .
C28 C 0.19639(9) 0.6780(4) 0.72046(17) 0.0232(7) Uani 1 1 d . . . . .
H28 H 0.165740 0.703979 0.715844 0.028 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 O21 2.417(2) . ?
Bi1 O22 2.4652(19) . ?
Bi1 N12 2.512(2) . ?
Bi1 N13 2.521(2) . ?
Bi1 N11 2.525(2) . ?
Bi1 Br1 2.7527(3) . ?
Bi1 Br2 2.9107(3) . ?
N11 C11 1.342(4) . ?
N11 C15 1.354(4) . ?
N12 C110 1.348(4) . ?
N12 C16 1.355(4) . ?
N13 C111 1.341(4) . ?
N13 C115 1.345(4) . ?
C11 C12 1.383(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.478(4) . ?
C16 C17 1.398(4) . ?
C17 C18 1.369(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.375(4) . ?
C18 H18 0.9500 . ?
C19 C110 1.394(4) . ?
C19 H19 0.9500 . ?
C110 C111 1.491(4) . ?
C111 C112 1.390(4) . ?
C112 C113 1.374(4) . ?
C112 H112 0.9500 . ?
C113 C114 1.376(4) . ?
C113 H113 0.9500 . ?
C114 C115 1.381(4) . ?
C114 H114 0.9500 . ?
C115 H115 0.9500 . ?
S21 C28 1.694(3) . ?
S21 C25 1.713(3) . ?
F21 C21 1.340(3) . ?
F22 C21 1.326(3) . ?
F23 C21 1.335(3) . ?
O21 C22 1.268(3) . ?
O22 C24 1.266(3) . ?
C21 C22 1.533(4) . ?
C22 C23 1.370(4) . ?
C23 C24 1.426(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.465(4) . ?
C25 C26 1.405(4) . ?
C26 C27 1.402(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.366(4) . ?
C27 H27 0.9500 . ?
C28 H28 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
O21 Bi1 O22 72.16(7) . . ?
O21 Bi1 N12 142.44(7) . . ?
O22 Bi1 N12 145.35(7) . . ?
O21 Bi1 N13 152.49(7) . . ?
O22 Bi1 N13 80.34(7) . . ?
N12 Bi1 N13 65.03(7) . . ?
O21 Bi1 N11 77.01(7) . . ?
O22 Bi1 N11 148.69(7) . . ?
N12 Bi1 N11 65.49(8) . . ?
N13 Bi1 N11 130.22(8) . . ?
O21 Bi1 Br1 91.91(6) . . ?
O22 Bi1 Br1 86.13(5) . . ?
N12 Bi1 Br1 89.91(5) . . ?
N13 Bi1 Br1 85.29(5) . . ?
N11 Bi1 Br1 89.58(5) . . ?
O21 Bi1 Br2 94.90(6) . . ?
O22 Bi1 Br2 96.18(5) . . ?
N12 Bi1 Br2 84.55(5) . . ?
N13 Bi1 Br2 88.78(5) . . ?
N11 Bi1 Br2 91.71(5) . . ?
Br1 Bi1 Br2 173.190(10) . . ?
C11 N11 C15 118.7(3) . . ?
C11 N11 Bi1 121.92(19) . . ?
C15 N11 Bi1 119.02(19) . . ?
C110 N12 C16 119.5(2) . . ?
C110 N12 Bi1 120.67(18) . . ?
C16 N12 Bi1 119.52(19) . . ?
C111 N13 C115 118.8(3) . . ?
C111 N13 Bi1 120.49(18) . . ?
C115 N13 Bi1 120.61(19) . . ?
N11 C11 C12 123.1(3) . . ?
N11 C11 H11 118.5 . . ?
C12 C11 H11 118.5 . . ?
C13 C12 C11 118.3(3) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C14 C13 C12 119.4(3) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
N11 C15 C14 120.6(3) . . ?
N11 C15 C16 117.4(2) . . ?
C14 C15 C16 121.9(3) . . ?
N12 C16 C17 120.9(3) . . ?
N12 C16 C15 117.4(2) . . ?
C17 C16 C15 121.7(3) . . ?
C18 C17 C16 119.1(3) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C110 118.8(3) . . ?
C18 C19 H19 120.6 . . ?
C110 C19 H19 120.6 . . ?
N12 C110 C19 121.4(3) . . ?
N12 C110 C111 116.7(2) . . ?
C19 C110 C111 121.8(3) . . ?
N13 C111 C112 121.1(3) . . ?
N13 C111 C110 117.0(3) . . ?
C112 C111 C110 121.9(3) . . ?
C113 C112 C111 119.6(3) . . ?
C113 C112 H112 120.2 . . ?
C111 C112 H112 120.2 . . ?
C112 C113 C114 119.4(3) . . ?
C112 C113 H113 120.3 . . ?
C114 C113 H113 120.3 . . ?
C113 C114 C115 118.4(3) . . ?
C113 C114 H114 120.8 . . ?
C115 C114 H114 120.8 . . ?
N13 C115 C114 122.6(3) . . ?
N13 C115 H115 118.7 . . ?
C114 C115 H115 118.7 . . ?
C28 S21 C25 92.07(14) . . ?
C22 O21 Bi1 131.45(18) . . ?
C24 O22 Bi1 133.96(18) . . ?
F22 C21 F23 107.0(2) . . ?
F22 C21 F21 106.8(2) . . ?
F23 C21 F21 106.6(2) . . ?
F22 C21 C22 112.4(2) . . ?
F23 C21 C22 114.1(2) . . ?
F21 C21 C22 109.4(2) . . ?
O21 C22 C23 130.1(3) . . ?
O21 C22 C21 112.1(2) . . ?
C23 C22 C21 117.8(2) . . ?
C22 C23 C24 123.7(3) . . ?
C22 C23 H23 118.1 . . ?
C24 C23 H23 118.1 . . ?
O22 C24 C23 124.7(3) . . ?
O22 C24 C25 117.1(2) . . ?
C23 C24 C25 118.2(2) . . ?
C26 C25 C24 130.9(3) . . ?
C26 C25 S21 111.1(2) . . ?
C24 C25 S21 117.9(2) . . ?
C27 C26 C25 111.3(3) . . ?
C27 C26 H26 124.4 . . ?
C25 C26 H26 124.4 . . ?
C28 C27 C26 113.3(3) . . ?
C28 C27 H27 123.3 . . ?
C26 C27 H27 123.3 . . ?
C27 C28 S21 112.3(2) . . ?
C27 C28 H28 123.9 . . ?
S21 C28 H28 123.9 . . ?

_refine_diff_density_max         0.673
_refine_diff_density_min         -1.062
_refine_diff_density_rms         0.114



