# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

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

data_121richy
_database_code_depnum_ccdc_archive 'CCDC 2176504'
loop_
_audit_author_name
_audit_author_address
'Richard Attila Varga'
;Facultate de Chimie si Inginerie Chimica UBB
Romania
;
_audit_update_record             
;
2022-06-02 deposited with the CCDC.	2024-02-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            dg245
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H53 N2 O2 Sb'
_chemical_formula_iupac          ?
_chemical_formula_weight         667.55

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   18.6622(10)
_cell_length_b                   10.6493(5)
_cell_length_c                   17.3555(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.402(2)
_cell_angle_gamma                90
_cell_volume                     3433.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.1923
_cell_measurement_theta_max      30.6740
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400

_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec Mo--I\mS 3.0 microfocus source'
_diffrn_source_type              ?
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer optics'

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            55025
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             3754
_reflns_number_gt                3389
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_gt          0.0437
_refine_ls_wR_factor_ref         0.0460
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_number_reflns         3754
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0124P)²+5.3359P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.296
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX3 2019.11-0'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  'Bruker APEX3 2019.11-0'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb Sb1 0.5 0.49164(2) 0.75 0.01173(5) Uani d T P S 1 . .
O O1 0.55680(6) 0.46611(10) 0.64648(6) 0.0154(2) Uani d . . . 1 . .
N N1 0.40154(7) 0.43135(13) 0.65599(8) 0.0159(3) Uani d . . . 1 . .
C C1 0.5 0.2933(2) 0.75 0.0149(5) Uani d T P S 1 . .
C C2 0.45944(9) 0.22959(15) 0.69120(10) 0.0185(3) Uani d . . . 1 . .
C C3 0.45899(10) 0.09851(16) 0.69199(13) 0.0290(4) Uani d . . . 1 . .
H H3 0.430697 0.053307 0.652934 0.035 Uiso calc U . R 1 . .
C C4 0.5 0.0348(2) 0.75 0.0348(7) Uani d T P S 1 . .
H H4 0.499999 -0.05436 0.750001 0.042 Uiso calc U P R 1 . .
C C5 0.42177(9) 0.30646(16) 0.62676(10) 0.0205(4) Uani d . . . 1 . .
H H5A 0.453924 0.317472 0.585041 0.025 Uiso calc U . R 1 . .
H H5B 0.377997 0.261762 0.604835 0.025 Uiso calc U . R 1 . .
C C6 0.39341(10) 0.52398(17) 0.59219(10) 0.0236(4) Uani d . . . 1 . .
H H6A 0.439551 0.534206 0.570219 0.035 Uiso calc U . R 1 . .
H H6B 0.378273 0.604843 0.612189 0.035 Uiso calc U . R 1 . .
H H6C 0.357043 0.494219 0.551916 0.035 Uiso calc U . R 1 . .
C C7 0.33382(9) 0.42062(16) 0.69315(10) 0.0188(3) Uani d . . . 1 . .
H H7A 0.294112 0.40189 0.653788 0.028 Uiso calc U . R 1 . .
H H7B 0.324176 0.49998 0.718832 0.028 Uiso calc U . R 1 . .
H H7C 0.338226 0.352857 0.731514 0.028 Uiso calc U . R 1 . .
C C8 0.62188(8) 0.48838(15) 0.62292(8) 0.0140(3) Uani d . . . 1 . .
C C9 0.66518(9) 0.38495(15) 0.60450(9) 0.0146(3) Uani d . . . 1 . .
C C10 0.73191(9) 0.40718(16) 0.57824(10) 0.0185(3) Uani d . . . 1 . .
H H10 0.761004 0.337976 0.566248 0.022 Uiso calc U . R 1 . .
C C11 0.75712(9) 0.52839(16) 0.56908(10) 0.0218(4) Uani d . . . 1 . .
H H11 0.802803 0.542051 0.550585 0.026 Uiso calc U . R 1 . .
C C12 0.71490(9) 0.62918(16) 0.58722(10) 0.0207(4) Uani d . . . 1 . .
H H12 0.732166 0.712101 0.58083 0.025 Uiso calc U . R 1 . .
C C13 0.64762(9) 0.61200(15) 0.61465(9) 0.0164(3) Uani d . . . 1 . .
C C14 0.63601(9) 0.25280(14) 0.61193(10) 0.0167(3) Uani d . . . 1 . .
H H14 0.601159 0.255293 0.652281 0.02 Uiso calc U . R 1 . .
C C15 0.59397(10) 0.21155(16) 0.53581(10) 0.0216(4) Uani d . . . 1 . .
H H15A 0.557172 0.274471 0.519986 0.032 Uiso calc U . R 1 . .
H H15B 0.570787 0.130477 0.543353 0.032 Uiso calc U . R 1 . .
H H15C 0.627113 0.203394 0.49553 0.032 Uiso calc U . R 1 . .
C C16 0.69343(10) 0.15581(16) 0.63784(11) 0.0246(4) Uani d . . . 1 . .
H H16A 0.670244 0.076091 0.648889 0.037 Uiso calc U . R 1 . .
H H16B 0.721767 0.185749 0.684647 0.037 Uiso calc U . R 1 . .
H H16C 0.725183 0.14327 0.59662 0.037 Uiso calc U . R 1 . .
C C17 0.60454(9) 0.72442(14) 0.63846(10) 0.0180(3) Uani d . . . 1 . .
H H17 0.554442 0.694916 0.644131 0.022 Uiso calc U . R 1 . .
C C18 0.63600(11) 0.77389(17) 0.71750(10) 0.0248(4) Uani d . . . 1 . .
H H18A 0.686355 0.798056 0.714659 0.037 Uiso calc U . R 1 . .
H H18B 0.63338 0.708037 0.756576 0.037 Uiso calc U . R 1 . .
H H18C 0.608374 0.847181 0.731763 0.037 Uiso calc U . R 1 . .
C C19 0.59968(11) 0.83066(16) 0.57936(10) 0.0246(4) Uani d . . . 1 . .
H H19A 0.579303 0.798529 0.529096 0.037 Uiso calc U . R 1 . .
H H19B 0.647906 0.864375 0.574467 0.037 Uiso calc U . R 1 . .
H H19C 0.568714 0.897407 0.596529 0.037 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Sb1 C1 . 2.113(2) ?
Sb1 O1 2_656 2.1872(11) ?
Sb1 O1 . 2.1872(11) ?
Sb1 N1 . 2.4263(14) ?
Sb1 N1 2_656 2.4263(14) ?
O1 C8 . 1.3386(18) ?
N1 C7 . 1.476(2) ?
N1 C6 . 1.480(2) ?
N1 C5 . 1.485(2) ?
C1 C2 . 1.389(2) ?
C1 C2 2_656 1.389(2) ?
C2 C3 . 1.396(2) ?
C2 C5 . 1.506(2) ?
C3 C4 . 1.383(2) ?
C8 C13 . 1.413(2) ?
C8 C9 . 1.420(2) ?
C9 C10 . 1.386(2) ?
C9 C14 . 1.519(2) ?
C10 C11 . 1.388(2) ?
C11 C12 . 1.385(2) ?
C12 C13 . 1.396(2) ?
C13 C17 . 1.521(2) ?
C14 C16 . 1.525(2) ?
C14 C15 . 1.536(2) ?
C17 C19 . 1.524(2) ?
C17 C18 . 1.534(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Sb1 O1 . 2_656 82.86(3) ?
C1 Sb1 O1 . . 82.86(3) ?
O1 Sb1 O1 2_656 . 165.72(6) ?
C1 Sb1 N1 . . 74.65(3) ?
O1 Sb1 N1 2_656 . 97.15(4) ?
O1 Sb1 N1 . . 79.03(4) ?
C1 Sb1 N1 . 2_656 74.65(3) ?
O1 Sb1 N1 2_656 2_656 79.03(4) ?
O1 Sb1 N1 . 2_656 97.15(4) ?
N1 Sb1 N1 . 2_656 149.31(6) ?
C8 O1 Sb1 . . 138.82(10) ?
C7 N1 C6 . . 110.30(13) ?
C7 N1 C5 . . 109.60(13) ?
C6 N1 C5 . . 110.66(13) ?
C7 N1 Sb1 . . 110.60(10) ?
C6 N1 Sb1 . . 110.15(10) ?
C5 N1 Sb1 . . 105.42(10) ?
C2 C1 C2 . 2_656 121.6(2) ?
C2 C1 Sb1 . . 119.22(10) ?
C2 C1 Sb1 2_656 . 119.22(10) ?
C1 C2 C3 . . 118.97(17) ?
C1 C2 C5 . . 117.68(15) ?
C3 C2 C5 . . 123.23(16) ?
C4 C3 C2 . . 119.58(19) ?
C3 C4 C3 . 2_656 121.3(2) ?
N1 C5 C2 . . 110.44(13) ?
O1 C8 C13 . . 121.53(14) ?
O1 C8 C9 . . 118.89(14) ?
C13 C8 C9 . . 119.57(14) ?
C10 C9 C8 . . 119.30(14) ?
C10 C9 C14 . . 121.76(14) ?
C8 C9 C14 . . 118.91(14) ?
C9 C10 C11 . . 121.41(15) ?
C12 C11 C10 . . 119.23(15) ?
C11 C12 C13 . . 121.67(16) ?
C12 C13 C8 . . 118.81(15) ?
C12 C13 C17 . . 120.32(14) ?
C8 C13 C17 . . 120.82(14) ?
C9 C14 C16 . . 113.89(14) ?
C9 C14 C15 . . 110.50(13) ?
C16 C14 C15 . . 110.35(14) ?
C13 C17 C19 . . 113.65(14) ?
C13 C17 C18 . . 110.23(14) ?
C19 C17 C18 . . 109.90(14) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 C2 C3 2_656 . . . 0.73(12) ?
Sb1 C1 C2 C3 . . . . -179.27(12) ?
C2 C1 C2 C5 2_656 . . . -175.44(16) ?
Sb1 C1 C2 C5 . . . . 4.56(16) ?
C1 C2 C3 C4 . . . . -1.5(2) ?
C5 C2 C3 C4 . . . . 174.49(14) ?
C2 C3 C4 C3 . . . 2_656 0.74(12) ?
C7 N1 C5 C2 . . . . -81.88(16) ?
C6 N1 C5 C2 . . . . 156.26(14) ?
Sb1 N1 C5 C2 . . . . 37.19(14) ?
C1 C2 C5 N1 . . . . -30.91(19) ?
C3 C2 C5 N1 . . . . 153.10(16) ?
Sb1 O1 C8 C13 . . . . -65.8(2) ?
Sb1 O1 C8 C9 . . . . 115.45(15) ?
O1 C8 C9 C10 . . . . 178.43(14) ?
C13 C8 C9 C10 . . . . -0.4(2) ?
O1 C8 C9 C14 . . . . 0.2(2) ?
C13 C8 C9 C14 . . . . -178.60(15) ?
C8 C9 C10 C11 . . . . -0.4(3) ?
C14 C9 C10 C11 . . . . 177.75(16) ?
C9 C10 C11 C12 . . . . 0.6(3) ?
C10 C11 C12 C13 . . . . 0.1(3) ?
C11 C12 C13 C8 . . . . -0.9(3) ?
C11 C12 C13 C17 . . . . 176.43(16) ?
O1 C8 C13 C12 . . . . -177.75(15) ?
C9 C8 C13 C12 . . . . 1.0(2) ?
O1 C8 C13 C17 . . . . 4.9(2) ?
C9 C8 C13 C17 . . . . -176.31(15) ?
C10 C9 C14 C16 . . . . 36.0(2) ?
C8 C9 C14 C16 . . . . -145.78(15) ?
C10 C9 C14 C15 . . . . -88.83(19) ?
C8 C9 C14 C15 . . . . 89.35(18) ?
C12 C13 C17 C19 . . . . 47.8(2) ?
C8 C13 C17 C19 . . . . -134.88(16) ?
C12 C13 C17 C18 . . . . -76.0(2) ?
C8 C13 C17 C18 . . . . 101.24(18) ?

####################################################################### 
# 
# 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_117richy
_database_code_depnum_ccdc_archive 'CCDC 2176505'
loop_
_audit_author_name
_audit_author_address
'Richard Attila Varga'
;Facultate de Chimie si Inginerie Chimica UBB
Romania
;
_audit_update_record             
;
2022-06-02 deposited with the CCDC.	2024-02-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            dg243
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H37 Bi N2 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         706.57

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   14.6780(9)
_cell_length_b                   22.2864(13)
_cell_length_c                   9.5439(6)
_cell_angle_alpha                90
_cell_angle_beta                 117.719(2)
_cell_angle_gamma                90
_cell_volume                     2763.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9730
_cell_measurement_theta_min      3.1587
_cell_measurement_theta_max      43.1936
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400

_exptl_absorpt_coefficient_mu    6.423
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_T_max  0.60

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec Mo--I\mS 3.0 microfocus source'
_diffrn_source_type              ?
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer optics'

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            135024
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         43.21
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             10348
_reflns_number_gt                9962
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0131
_refine_ls_R_factor_gt           0.0121
_refine_ls_wR_factor_gt          0.0323
_refine_ls_wR_factor_ref         0.0325
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_refine_ls_number_reflns         10348
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0155P)²+1.0482P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.102
_refine_diff_density_min         -1.205
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX3 2019.11-0'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  'Bruker APEX3 2019.11-0'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi Bi1 0.5 0.64037(2) 0.25 0.01145(10) Uani d T P S 1 . .
O O1 0.63641(5) 0.65196(3) 0.19172(9) 0.02008(11) Uani d . . . 1 . .
N N1 0.60387(5) 0.67535(3) 0.53597(7) 0.01484(9) Uani d . . . 1 . .
C C1 0.5 0.73970(4) 0.25 0.01225(12) Uani d T P S 1 . .
C C2 0.53174(5) 0.77034(3) 0.39218(8) 0.01406(9) Uani d . . . 1 . .
O O2 0.76668(4) 0.67500(3) 0.07576(7) 0.01627(8) Uani d . . . 1 . .
C C3 0.53332(6) 0.83309(3) 0.39266(10) 0.01821(11) Uani d . . . 1 . .
H H3 0.556881 0.854532 0.489338 0.022 Uiso calc U . R 1 . .
O O3 0.65911(7) 0.55437(4) 0.37407(12) 0.03341(19) Uani d . . . 1 . .
C C4 0.5 0.86391(5) 0.25 0.01985(18) Uani d T P S 1 . .
H H4 0.5 0.906539 0.249998 0.024 Uiso calc U P R 1 . .
C C5 0.55855(6) 0.73414(4) 0.54047(9) 0.01749(11) Uani d . . . 1 . .
H H5A 0.608103 0.757004 0.633867 0.021 Uiso calc U . R 1 . .
H H5B 0.49559 0.727697 0.55188 0.021 Uiso calc U . R 1 . .
C C7 0.59579(8) 0.63369(4) 0.64946(11) 0.02197(14) Uani d . . . 1 . .
H H7A 0.523083 0.626814 0.619511 0.033 Uiso calc U . R 1 . .
H H7B 0.630413 0.651064 0.755939 0.033 Uiso calc U . R 1 . .
H H7C 0.628511 0.595472 0.648475 0.033 Uiso calc U . R 1 . .
C C6 0.71189(6) 0.68190(4) 0.56781(10) 0.02091(13) Uani d . . . 1 . .
H H6A 0.742573 0.642096 0.577124 0.031 Uiso calc U . R 1 . .
H H6B 0.750565 0.704071 0.666834 0.031 Uiso calc U . R 1 . .
H H6C 0.714248 0.703885 0.48063 0.031 Uiso calc U . R 1 . .
C C8 0.71479(5) 0.61514(3) 0.22870(9) 0.01424(10) Uani d . . . 1 . .
C C9 0.78687(5) 0.62544(3) 0.17121(8) 0.01271(9) Uani d . . . 1 . .
C C10 0.87048(5) 0.58755(3) 0.20905(9) 0.01590(10) Uani d . . . 1 . .
H H10 0.916298 0.594965 0.16621 0.019 Uiso calc U . R 1 . .
C C11 0.88725(6) 0.53872(4) 0.30970(10) 0.01907(12) Uani d . . . 1 . .
H H11 0.945415 0.513575 0.337488 0.023 Uiso calc U . R 1 . .
C C12 0.81878(6) 0.52685(4) 0.36935(10) 0.01979(12) Uani d . . . 1 . .
H H12 0.830107 0.493889 0.438665 0.024 Uiso calc U . R 1 . .
C C13 0.73325(6) 0.56396(4) 0.32608(10) 0.01795(12) Uani d . . . 1 . .
C C14 0.84047(6) 0.68876(4) 0.02294(10) 0.02046(13) Uani d . . . 1 . .
H H14A 0.84086 0.656811 -0.047341 0.031 Uiso calc U . R 1 . .
H H14B 0.908889 0.691992 0.114415 0.031 Uiso calc U . R 1 . .
H H14C 0.822412 0.726935 -0.034612 0.031 Uiso calc U . R 1 . .
C C15 0.65650(8) 0.49918(4) 0.44293(12) 0.02350(14) Uani d . . . 1 . .
H H15A 0.595182 0.497458 0.458702 0.035 Uiso calc U . R 1 . .
H H15B 0.718276 0.495132 0.545268 0.035 Uiso calc U . R 1 . .
H H15C 0.654237 0.466416 0.37289 0.035 Uiso calc U . R 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Bi1 C1 . 2.2137(9) ?
Bi1 O1 . 2.3283(6) ?
Bi1 O1 2_655 2.3284(6) ?
Bi1 N1 . 2.5514(7) ?
Bi1 N1 2_655 2.5514(7) ?
O1 C8 . 1.3206(9) ?
N1 C7 . 1.4727(10) ?
N1 C6 . 1.4763(10) ?
N1 C5 . 1.4791(10) ?
C1 C2 2_655 1.3916(8) ?
C1 C2 . 1.3916(8) ?
C2 C3 . 1.3986(10) ?
C2 C5 . 1.5135(11) ?
O2 C9 . 1.3736(9) ?
O2 C14 . 1.4245(9) ?
C3 C4 . 1.3948(10) ?
O3 C13 . 1.3796(10) ?
O3 C15 . 1.4034(11) ?
C8 C13 . 1.4156(10) ?
C8 C9 . 1.4187(9) ?
C9 C10 . 1.3917(10) ?
C10 C11 . 1.3958(11) ?
C11 C12 . 1.3915(12) ?
C12 C13 . 1.3959(10) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Bi1 O1 . . 83.627(16) ?
C1 Bi1 O1 . 2_655 83.629(16) ?
O1 Bi1 O1 . 2_655 167.26(3) ?
C1 Bi1 N1 . . 72.211(15) ?
O1 Bi1 N1 . . 93.97(2) ?
O1 Bi1 N1 2_655 . 82.12(2) ?
C1 Bi1 N1 . 2_655 72.210(15) ?
O1 Bi1 N1 . 2_655 82.12(2) ?
O1 Bi1 N1 2_655 2_655 93.97(2) ?
N1 Bi1 N1 . 2_655 144.42(3) ?
C8 O1 Bi1 . . 127.32(5) ?
C7 N1 C6 . . 110.92(7) ?
C7 N1 C5 . . 110.24(6) ?
C6 N1 C5 . . 111.15(7) ?
C7 N1 Bi1 . . 112.44(5) ?
C6 N1 Bi1 . . 107.50(5) ?
C5 N1 Bi1 . . 104.40(4) ?
C2 C1 C2 2_655 . 121.23(9) ?
C2 C1 Bi1 2_655 . 119.39(4) ?
C2 C1 Bi1 . . 119.39(4) ?
C1 C2 C3 . . 119.43(7) ?
C1 C2 C5 . . 118.28(7) ?
C3 C2 C5 . . 122.22(7) ?
C9 O2 C14 . . 116.28(6) ?
C4 C3 C2 . . 119.44(7) ?
C13 O3 C15 . . 119.26(7) ?
C3 C4 C3 . 2_655 120.98(10) ?
N1 C5 C2 . . 111.71(6) ?
O1 C8 C13 . . 123.58(6) ?
O1 C8 C9 . . 120.65(6) ?
C13 C8 C9 . . 115.77(6) ?
O2 C9 C10 . . 123.51(6) ?
O2 C9 C8 . . 114.64(6) ?
C10 C9 C8 . . 121.85(7) ?
C9 C10 C11 . . 120.24(7) ?
C12 C11 C10 . . 120.00(7) ?
C11 C12 C13 . . 119.19(7) ?
O3 C13 C12 . . 123.35(7) ?
O3 C13 C8 . . 113.77(6) ?
C12 C13 C8 . . 122.87(7) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 C2 C3 2_655 . . . -1.00(5) ?
Bi1 C1 C2 C3 . . . . 179.00(5) ?
C2 C1 C2 C5 2_655 . . . 176.06(7) ?
Bi1 C1 C2 C5 . . . . -3.94(7) ?
C1 C2 C3 C4 . . . . 2.00(10) ?
C5 C2 C3 C4 . . . . -174.95(6) ?
C2 C3 C4 C3 . . . 2_655 -1.00(5) ?
C7 N1 C5 C2 . . . . -160.37(7) ?
C6 N1 C5 C2 . . . . 76.22(8) ?
Bi1 N1 C5 C2 . . . . -39.39(7) ?
C1 C2 C5 N1 . . . . 32.88(9) ?
C3 C2 C5 N1 . . . . -150.14(7) ?
Bi1 O1 C8 C13 . . . . -6.46(12) ?
Bi1 O1 C8 C9 . . . . 173.71(5) ?
C14 O2 C9 C10 . . . . -3.83(11) ?
C14 O2 C9 C8 . . . . 176.59(7) ?
O1 C8 C9 O2 . . . . -0.79(11) ?
C13 C8 C9 O2 . . . . 179.37(7) ?
O1 C8 C9 C10 . . . . 179.63(7) ?
C13 C8 C9 C10 . . . . -0.21(11) ?
O2 C9 C10 C11 . . . . 178.61(7) ?
C8 C9 C10 C11 . . . . -1.84(11) ?
C9 C10 C11 C12 . . . . 1.66(12) ?
C10 C11 C12 C13 . . . . 0.57(13) ?
C15 O3 C13 C12 . . . . -13.07(16) ?
C15 O3 C13 C8 . . . . 167.02(9) ?
C11 C12 C13 O3 . . . . 177.35(9) ?
C11 C12 C13 C8 . . . . -2.75(14) ?
O1 C8 C13 O3 . . . . 2.60(13) ?
C9 C8 C13 O3 . . . . -177.56(8) ?
O1 C8 C13 C12 . . . . -177.31(9) ?
C9 C8 C13 C12 . . . . 2.53(12) ?

