# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_1MeOH
_database_code_depnum_ccdc_archive 'CCDC 2183351'
loop_
_audit_author_name
_audit_author_address
'Erik Svensson Grape'
;Stockholm University
Sweden
;
_audit_update_record             
;
2022-08-16 deposited with the CCDC.	2022-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H7 Bi O6'
_chemical_formula_weight         408.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   7.62(4)
_cell_length_b                   8.38(4)
_cell_length_c                   16.68(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1066(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25993
_cell_measurement_theta_min      0.082
_cell_measurement_theta_max      0.897

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.544
_exptl_crystal_F_000             195
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.000
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.0251
_diffrn_radiation_type           electron
_diffrn_source                   ?
_diffrn_measurement_device_type  'JEOL JEM-2100 LaB6'
_diffrn_measurement_method       'continuous rotation'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25993
_diffrn_reflns_av_unetI/netI     0.1257
_diffrn_reflns_av_R_equivalents  0.2958
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         0.086
_diffrn_reflns_theta_max         0.933
_diffrn_reflns_theta_full        0.863
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2222
_reflns_number_gt                1833
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_max     0.897
_reflns_Friedel_fraction_full    1.000

_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       
;
Stef Smeets, Bin Wang, Magdalena O. Cichocka, Jonas Angstrom, Wei Wan.
(2018, April 11). Instamatic (Version 0.6). Zenodo.
http://doi.org/10.5281/zenodo.1217026
;
_computing_cell_refinement       
;
Kabsch, W. (2010). XDS. Acta Crystallographica Section D:
Biological Crystallography, 66(2), 125-132.
;
_computing_data_reduction        
;
Kabsch, W. (2010). XDS. Acta Crystallographica Section D:
Biological Crystallography, 66(2), 125-132.
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1508P)²+0.7739P] 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_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2222
_refine_ls_number_parameters     139
_refine_ls_number_restraints     208
_refine_ls_R_factor_all          0.1541
_refine_ls_R_factor_gt           0.1399
_refine_ls_wR_factor_ref         0.3500
_refine_ls_wR_factor_gt          0.3413
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_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 0.3369(3) 0.7094(4) 0.53272(14) 0.0384(16) Uani 1 1 d . . . . .
O1 O 0.228(3) 1.092(3) 0.1097(11) 0.066(7) Uani 1 1 d . . . . .
O2 O -0.019(3) 1.062(6) 0.181(2) 0.125(14) Uani 1 1 d . . . . .
O3 O 0.1833(18) 0.825(3) 0.4478(8) 0.050(3) Uani 1 1 d . U . . .
O4 O 0.5308(19) 0.844(3) 0.4473(9) 0.050(3) Uani 1 1 d . U . . .
O5 O 0.704(2) 0.976(3) 0.3162(11) 0.057(3) Uani 1 1 d . U . . .
H5 H 0.737589 1.015081 0.273787 0.085 Uiso 1 1 calc R U . . .
O6 O 0.288(3) 0.500(5) 0.4219(13) 0.090(10) Uani 1 1 d . . . . .
H6 H 0.181023 0.512487 0.419069 0.135 Uiso 1 1 calc R U . . .
C1 C 0.148(3) 1.051(4) 0.1739(13) 0.066(8) Uani 1 1 d D . . . .
C2 C 0.252(2) 1.003(3) 0.2451(11) 0.051(3) Uani 1 1 d D U . . .
C7 C 0.435(3) 1.001(3) 0.2456(11) 0.052(3) Uani 1 1 d D U . . .
H7 H 0.494648 1.028256 0.198905 0.062 Uiso 1 1 calc R U . . .
C6 C 0.534(2) 0.959(3) 0.3145(10) 0.051(3) Uani 1 1 d D U . . .
C5 C 0.437(2) 0.894(3) 0.3789(11) 0.051(3) Uani 1 1 d D U . . .
C4 C 0.256(2) 0.885(3) 0.3784(11) 0.050(3) Uani 1 1 d D U . . .
C3 C 0.169(2) 0.939(3) 0.3114(10) 0.051(3) Uani 1 1 d D U . . .
H3 H 0.047064 0.932141 0.310775 0.061 Uiso 1 1 calc R U . . .
C8 C 0.329(6) 0.324(4) 0.421(2) 0.121(15) Uani 1 1 d . . . . .
H8A H 0.452970 0.308939 0.426433 0.182 Uiso 1 1 calc R U . . .
H8B H 0.289108 0.278123 0.371746 0.182 Uiso 1 1 calc R U . . .
H8C H 0.269805 0.273043 0.465266 0.182 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 O3 2.077(17) . ?
Bi1 O1 2.16(2) 2_575 ?
Bi1 O4 2.344(17) . ?
Bi1 O4 2.399(19) 4_466 ?
Bi1 O6 2.58(3) . ?
Bi1 O3 2.675(19) 4_566 ?
O1 C1 1.28(3) . ?
O2 C1 1.28(4) . ?
O3 C4 1.38(2) . ?
O4 C5 1.41(2) . ?
O5 C6 1.30(2) . ?
O5 H5 0.8200 . ?
O6 C8 1.51(5) . ?
O6 H6 0.8200 . ?
C1 C2 1.48(3) . ?
C2 C3 1.38(2) . ?
C2 C7 1.40(3) . ?
C7 C6 1.42(2) . ?
C7 H7 0.9300 . ?
C6 C5 1.415(19) . ?
C5 C4 1.381(19) . ?
C4 C3 1.38(2) . ?
C3 H3 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Bi1 O1 85.3(8) . 2_575 ?
O3 Bi1 O4 73.4(6) . . ?
O1 Bi1 O4 97.6(9) 2_575 . ?
O3 Bi1 O4 68.6(6) . 4_466 ?
O1 Bi1 O4 80.8(8) 2_575 4_466 ?
O4 Bi1 O4 142.0(4) . 4_466 ?
O3 Bi1 O6 75.3(9) . . ?
O1 Bi1 O6 156.7(8) 2_575 . ?
O4 Bi1 O6 89.2(9) . . ?
O4 Bi1 O6 80.2(8) 4_466 . ?
O3 Bi1 O3 133.5(4) . 4_566 ?
O1 Bi1 O3 103.6(7) 2_575 4_566 ?
O4 Bi1 O3 60.3(6) . 4_566 ?
O4 Bi1 O3 157.3(6) 4_466 4_566 ?
O6 Bi1 O3 99.1(7) . 4_566 ?
C1 O1 Bi1 126(2) . 2_574 ?
C4 O3 Bi1 121.0(12) . . ?
C4 O3 Bi1 122.7(10) . 4_466 ?
Bi1 O3 Bi1 115.0(7) . 4_466 ?
C5 O4 Bi1 108.5(11) . . ?
C5 O4 Bi1 131.3(11) . 4_566 ?
Bi1 O4 Bi1 115.9(7) . 4_566 ?
C6 O5 H5 109.5 . . ?
C8 O6 Bi1 130(2) . . ?
C8 O6 H6 109.5 . . ?
Bi1 O6 H6 95.6 . . ?
O1 C1 O2 122(3) . . ?
O1 C1 C2 119(2) . . ?
O2 C1 C2 118(2) . . ?
C3 C2 C7 116.5(18) . . ?
C3 C2 C1 120.2(18) . . ?
C7 C2 C1 122.8(17) . . ?
C6 C7 C2 122.7(17) . . ?
C6 C7 H7 118.6 . . ?
C2 C7 H7 118.6 . . ?
O5 C6 C5 122.9(16) . . ?
O5 C6 C7 121.3(16) . . ?
C5 C6 C7 115.7(16) . . ?
C6 C5 C4 122.4(17) . . ?
C6 C5 O4 117.9(15) . . ?
C4 C5 O4 119.6(15) . . ?
C3 C4 C5 118.1(17) . . ?
C3 C4 O3 127.2(15) . . ?
C5 C4 O3 114.6(15) . . ?
C4 C3 C2 123.8(18) . . ?
C4 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
O6 C8 H8A 109.5 . . ?
O6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.083




# start Validation Reply Form
_vrf_RINTA01_1MeOH               
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Higher than expected R-values are commonly observed for electron
diffraction data due to dynamical effects (multiple scattering).
;
_vrf_PLAT020_1MeOH               
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.296 Report
RESPONSE: Higher than expected R-values are commonly observed for electron
diffraction data due to dynamical effects (multiple scattering).
;
_vrf_PLAT342_1MeOH               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02857 Ang.
RESPONSE: The relatively large ESDs on the unit cell parameters, as acquired
from the 3D ED data, leads to the relatively low precision in bond lengths.
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 2183354'
loop_
_audit_author_name
_audit_author_address
'Erik Svensson Grape'
;Stockholm University
Sweden
;
_audit_update_record             
;
2022-08-16 deposited with the CCDC.	2022-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H3 Bi O5'
_chemical_formula_weight         376.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.75(6)
_cell_length_b                   7.64(4)
_cell_length_c                   10.11(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.8(2)
_cell_angle_gamma                90
_cell_volume                     878(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7034
_cell_measurement_theta_min      0.113
_cell_measurement_theta_max      0.897

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.846
_exptl_crystal_F_000             169
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.000
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.0251
_diffrn_radiation_type           electron
_diffrn_source                   ?
_diffrn_measurement_device_type  'JOEL JEM-2100 LaB6'
_diffrn_measurement_method       'continuous rotation'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7034
_diffrn_reflns_av_unetI/netI     0.2051
_diffrn_reflns_av_R_equivalents  0.2322
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         0.113
_diffrn_reflns_theta_max         0.897
_diffrn_reflns_theta_full        0.863
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measured_fraction_theta_full 0.905
_diffrn_reflns_Laue_measured_fraction_max 0.888
_diffrn_reflns_Laue_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_point_group_measured_fraction_full 0.905
_reflns_number_total             1590
_reflns_number_gt                1240
_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       
;
Stef Smeets, Bin Wang, Magdalena O. Cichocka, Jonas Angstrom, Wei Wan.
(2018, April 11). Instamatic (Version 0.6). Zenodo.
http://doi.org/10.5281/zenodo.1217026
;
_computing_cell_refinement       
;
Kabsch, W. (2010). XDS. Acta Crystallographica Section D:
Biological Crystallography, 66(2), 125-132.
;
_computing_data_reduction        
;
Kabsch, W. (2010). XDS. Acta Crystallographica Section D:
Biological Crystallography, 66(2), 125-132.
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2298P)²+2.1700P] 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         1590
_refine_ls_number_parameters     119
_refine_ls_number_restraints     176
_refine_ls_R_factor_all          0.2390
_refine_ls_R_factor_gt           0.2043
_refine_ls_wR_factor_ref         0.5092
_refine_ls_wR_factor_gt          0.4858
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_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 0.5361(3) 0.9729(3) 0.7056(3) 0.0440(12) Uani 1 1 d . . . . .
O1 O 0.132(5) 0.476(4) 0.728(3) 0.130(10) Uani 1 1 d . U . . .
H1 H 0.102407 0.402858 0.769207 0.195 Uiso 1 1 calc DR U . . .
O2 O 0.076(4) 0.271(4) 0.570(3) 0.129(10) Uani 1 1 d D U . . .
O3 O 0.404(2) 0.376(2) 0.2955(17) 0.055(3) Uani 1 1 d . U . . .
O4 O 0.467(2) 0.7247(19) 0.3407(17) 0.055(3) Uani 1 1 d . U . . .
O5 O 0.390(2) 0.921(2) 0.5308(17) 0.056(3) Uani 1 1 d . U . . .
C1 C 0.146(4) 0.407(4) 0.612(3) 0.117(10) Uani 1 1 d D U . . .
C2 C 0.217(2) 0.485(2) 0.541(2) 0.057(3) Uani 1 1 d D U . . .
C3 C 0.272(2) 0.385(2) 0.453(2) 0.055(3) Uani 1 1 d . U . . .
H3 H 0.252115 0.267524 0.437096 0.067 Uiso 1 1 calc R U . . .
C4 C 0.358(2) 0.463(2) 0.387(2) 0.053(3) Uani 1 1 d . U . . .
C5 C 0.380(3) 0.653(2) 0.398(2) 0.054(3) Uani 1 1 d . U . . .
C6 C 0.346(3) 0.750(2) 0.508(2) 0.054(3) Uani 1 1 d . U . . .
C7 C 0.256(3) 0.672(2) 0.566(2) 0.055(3) Uani 1 1 d . U . . .
H7 H 0.221689 0.741605 0.620551 0.066 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 O5 2.16(2) . ?
Bi1 O3 2.30(2) 4_576 ?
Bi1 O4 2.315(17) 4_576 ?
Bi1 O4 2.356(19) 3_676 ?
O1 C1 1.34(3) . ?
O1 H1 0.8200 . ?
O2 C1 1.32(4) . ?
O3 C4 1.36(2) . ?
O4 C5 1.41(3) . ?
O5 C6 1.40(3) . ?
C1 C2 1.368(19) . ?
C2 C3 1.44(3) . ?
C2 C7 1.51(3) . ?
C3 C4 1.47(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.47(3) . ?
C5 C6 1.47(2) . ?
C6 C7 1.46(3) . ?
C7 H7 0.9300 . ?

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
O5 Bi1 O3 86.6(8) . 4_576 ?
O5 Bi1 O4 92.2(8) . 4_576 ?
O3 Bi1 O4 73.9(7) 4_576 4_576 ?
O5 Bi1 O4 92.7(7) . 3_676 ?
O3 Bi1 O4 66.9(6) 4_576 3_676 ?
O4 Bi1 O4 140.0(4) 4_576 3_676 ?
C1 O1 H1 109.5 . . ?
C4 O3 Bi1 116.7(13) . 4_575 ?
C5 O4 Bi1 113.0(11) . 4_575 ?
C5 O4 Bi1 119.0(13) . 3_676 ?
Bi1 O4 Bi1 120.9(7) 4_575 3_676 ?
C6 O5 Bi1 119.2(16) . . ?
O2 C1 O1 113(3) . . ?
O2 C1 C2 126(2) . . ?
O1 C1 C2 121(3) . . ?
C1 C2 C3 121(2) . . ?
C1 C2 C7 122(2) . . ?
C3 C2 C7 116.0(18) . . ?
C2 C3 C4 122.0(17) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
O3 C4 C5 116.2(17) . . ?
O3 C4 C3 123.1(16) . . ?
C5 C4 C3 119.6(17) . . ?
O4 C5 C6 118.5(17) . . ?
O4 C5 C4 118.7(17) . . ?
C6 C5 C4 118.8(16) . . ?
O5 C6 C7 125.8(16) . . ?
O5 C6 C5 116.1(17) . . ?
C7 C6 C5 117.2(18) . . ?
C6 C7 C2 122.9(16) . . ?
C6 C7 H7 118.5 . . ?
C2 C7 H7 118.5 . . ?

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.139



# start Validation Reply Form
_vrf_RINTA01_2                   
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Higher than expected R-values are often encountered in refinements
against electron diffraction data, arising from dynamical effects (multiple
scattering).
;
_vrf_PLAT084_2                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.51 Report
RESPONSE: Higher than expected R-values are often encountered in refinements
against electron diffraction data, arising from dynamical effects (multiple
scattering).
;
_vrf_PLAT020_2                   
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.232 Report
RESPONSE: Higher than expected R-values are often encountered in refinements
against electron diffraction data, arising from dynamical effects (multiple
scattering).
;
_vrf_PLAT082_2                   
;
PROBLEM: High R1 Value ..................................       0.20 Report
RESPONSE: Higher than expected R-values are often encountered in refinements
against electron diffraction data, arising from dynamical effects (multiple
scattering).
;
_vrf_PLAT250_2                   
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        6.1 Note
RESPONSE: The missing wedge of the data likely contributes to this effect.
Additionally, the orientation of the molecules in the layered structure should
permit a higher degree of motion along the affected direction.
;
_vrf_PLAT420_2                   
;
PROBLEM: D-H Bond Without Acceptor  O1       --H1       .     Please Check
RESPONSE: No intra-layer solvent molecules could be located from the difference
map.
;
_vrf_PLAT430_2                   
;
PROBLEM: Short Inter D...A Contact  O3       ..O4       .       2.57 Ang.
RESPONSE: These oxygens are both coordinated to a Bi3+ cation.
;
_vrf_PLAT149_2                   
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.20 Degree
RESPONSE: The larger than expected errors in cell parameters arises from the
general uncertainty in unit cell parameters from 3D ED data.
;
_vrf_PLAT342_2                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03286 Ang.
RESPONSE: The larger than expected errors in cell parameters arises from the
general uncertainty in unit cell parameters from 3D ED data.
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1EtOH_stored
_database_code_depnum_ccdc_archive 'CCDC 2183353'
loop_
_audit_author_name
_audit_author_address
'Erik Svensson Grape'
;Stockholm University
Sweden
;
_audit_update_record             
;
2022-08-16 deposited with the CCDC.	2022-08-29 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 Bi O6'
_chemical_formula_weight         422.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   7.73(4)
_cell_length_b                   6.84(3)
_cell_length_c                   16.87(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     891(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3234
_cell_measurement_theta_min      0.085
_cell_measurement_theta_max      0.896

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.147
_exptl_crystal_F_000             209
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.000
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.0251
_diffrn_radiation_type           electron
_diffrn_source                   ?
_diffrn_measurement_device_type  'JEOL JEM-2100 LaB6'
_diffrn_measurement_method       'continuous rotation'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3234
_diffrn_reflns_av_unetI/netI     0.1871
_diffrn_reflns_av_R_equivalents  0.1407
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         0.085
_diffrn_reflns_theta_max         0.896
_diffrn_reflns_theta_full        0.863
_diffrn_measured_fraction_theta_max 0.724
_diffrn_measured_fraction_theta_full 0.729
_diffrn_reflns_Laue_measured_fraction_max 0.724
_diffrn_reflns_Laue_measured_fraction_full 0.729
_diffrn_reflns_point_group_measured_fraction_max 0.706
_diffrn_reflns_point_group_measured_fraction_full 0.715
_reflns_number_total             1278
_reflns_number_gt                993
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_max     0.681
_reflns_Friedel_fraction_full    0.694

_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       
;
Stef Smeets, Bin Wang, Magdalena O. Cichocka, Jonas Angstrom, Wei Wan.
(2018, April 11). Instamatic (Version 0.6). Zenodo.
http://doi.org/10.5281/zenodo.1217026
;
_computing_cell_refinement       
;
Kabsch, W. (2010). XDS. Acta Crystallographica Section D:
Biological Crystallography, 66(2), 125-132.
;
_computing_data_reduction        
;
Kabsch, W. (2010). XDS. Acta Crystallographica Section D:
Biological Crystallography, 66(2), 125-132.
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.7000P)²+6.7000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       379(155)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1278
_refine_ls_number_parameters     66
_refine_ls_number_restraints     53
_refine_ls_R_factor_all          0.3377
_refine_ls_R_factor_gt           0.3069
_refine_ls_wR_factor_ref         0.6940
_refine_ls_wR_factor_gt          0.6519
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.917
_refine_ls_shift/su_max          0.081
_refine_ls_shift/su_mean         0.010

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 0.1793(6) 0.2825(7) 0.0364(3) 0.0301(9) Uiso 1 1 d D . . . .
O1 O 0.173(5) 0.037(4) 0.0898(13) 0.097(18) Uiso 1 1 d D . . . .
O2 O -0.006(3) -0.167(5) 0.1497(19) 0.16(4) Uiso 1 1 d D . . . .
O3 O 0.151(4) -0.202(4) 0.4411(12) 0.057(7) Uiso 1 1 d D U . . .
O4 O 0.503(3) -0.1913(11) 0.4311(11) 0.045(6) Uiso 1 1 d D U . . .
O5 O 0.681(2) -0.123(3) 0.2915(19) 0.043(7) Uiso 1 1 d D . . . .
H5 H 0.715842 -0.101734 0.246424 0.064 Uiso 1 1 d R U . . .
O6 O 0.215(3) 0.507(3) -0.0451(9) 0.71(2) Uiso 1 1 d D U . . .
H6 H 0.201126 0.496644 -0.099749 1.067 Uiso 1 1 d R U . . .
C1 C 0.138(2) -0.071(2) 0.1514(9) 0.051(12) Uiso 1 1 d D . . . .
C2 C 0.224(2) -0.104(4) 0.2199(9) 0.09(2) Uiso 1 1 d D . . . .
C3 C 0.130(3) -0.136(4) 0.2915(9) 0.045(11) Uiso 1 1 d D . . . .
H3 H 0.010052 -0.135532 0.290827 0.054 Uiso 1 1 calc R U . . .
C4 C 0.220(2) -0.169(4) 0.3643(9) 0.048(7) Uiso 1 1 d D U . . .
C5 C 0.4031(19) -0.1627(7) 0.3635(8) 0.050(7) Uiso 1 1 d D U . . .
C6 C 0.4999(18) -0.126(3) 0.2944(9) 0.050(7) Uiso 1 1 d D U . . .
C7 C 0.408(2) -0.094(4) 0.2221(10) 0.038(8) Uiso 1 1 d D U . . .
H7 H 0.469584 -0.067635 0.175883 0.045 Uiso 1 1 calc R U . . .
C8 C 0.256(3) 0.698(2) -0.0058(10) 0.71(2) Uiso 1 1 d D U . . .
H8A H 0.150185 0.755282 0.014234 0.854 Uiso 1 1 calc R U . . .
H8B H 0.304156 0.786783 -0.044906 0.854 Uiso 1 1 calc R U . . .
C9 C 0.3827(18) 0.6766(15) 0.0613(8) 0.72(4) Uiso 1 1 d D U . . .
H9A H 0.404651 0.802658 0.084342 1.076 Uiso 1 1 calc R U . . .
H9B H 0.335044 0.591096 0.100832 1.076 Uiso 1 1 calc R U . . .
H9C H 0.489038 0.622601 0.041683 1.076 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 O1 1.90(2) . ?
Bi1 O6 2.08(2) . ?
Bi1 O3 2.15(3) 2_554 ?
Bi1 O4 2.35(2) 2_554 ?
Bi1 O4 2.52(3) 4_655 ?
Bi1 O3 2.58(3) 4 ?
O1 C1 1.30(2) . ?
O2 C1 1.29(2) . ?
O3 C4 1.42(2) . ?
O4 C5 1.39(2) . ?
O5 C6 1.40(2) . ?
O5 H5 0.8200 . ?
O6 C8 1.499(18) . ?
O6 H6 0.9300 . ?
C1 C2 1.351(19) . ?
C2 C3 1.425(19) . ?
C2 C7 1.43(2) . ?
C3 C4 1.428(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.416(19) . ?
C5 C6 1.409(18) . ?
C6 C7 1.425(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.50(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Bi1 O6 165.1(10) . . ?
O1 Bi1 O3 98.3(12) . 2_554 ?
O6 Bi1 O3 67.2(9) . 2_554 ?
O1 Bi1 O4 96.3(11) . 2_554 ?
O6 Bi1 O4 77.0(6) . 2_554 ?
O3 Bi1 O4 74.5(9) 2_554 2_554 ?
O1 Bi1 O4 89.0(13) . 4_655 ?
O6 Bi1 O4 87.9(7) . 4_655 ?
O3 Bi1 O4 65.6(9) 2_554 4_655 ?
O4 Bi1 O4 140.1(7) 2_554 4_655 ?
O1 Bi1 O3 86.7(14) . 4 ?
O6 Bi1 O3 101.4(9) . 4 ?
O3 Bi1 O3 136.4(9) 2_554 4 ?
O4 Bi1 O3 61.9(7) 2_554 4 ?
O4 Bi1 O3 158.0(7) 4_655 4 ?
C1 O1 Bi1 152(2) . . ?
C4 O3 Bi1 120(2) . 2 ?
C4 O3 Bi1 120.8(18) . 4_545 ?
Bi1 O3 Bi1 118.8(9) 2 4_545 ?
C5 O4 Bi1 108.8(15) . 2 ?
C5 O4 Bi1 136.9(15) . 4_645 ?
Bi1 O4 Bi1 113.6(7) 2 4_645 ?
C6 O5 H5 111.5 . . ?
C8 O6 Bi1 112.2(11) . . ?
C8 O6 H6 121.9 . . ?
Bi1 O6 H6 125.8 . . ?
O2 C1 O1 117(2) . . ?
O2 C1 C2 110.8(19) . . ?
O1 C1 C2 132(2) . . ?
C1 C2 C3 120.2(15) . . ?
C1 C2 C7 120.2(15) . . ?
C3 C2 C7 119.5(14) . . ?
C2 C3 C4 120.5(16) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 O3 112.9(18) . . ?
C5 C4 C3 118.1(14) . . ?
O3 C4 C3 129.0(19) . . ?
O4 C5 C6 114.1(16) . . ?
O4 C5 C4 122.9(15) . . ?
C6 C5 C4 123.0(13) . . ?
O5 C6 C5 124.2(18) . . ?
O5 C6 C7 117.6(18) . . ?
C5 C6 C7 118.2(13) . . ?
C2 C7 C6 120.7(14) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
O6 C8 C9 112.9(13) . . ?
O6 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
O6 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         2.214
_refine_diff_density_min         -0.878
_refine_diff_density_rms         0.145



# start Validation Reply Form
_vrf_ATOM007_1EtOH_stored        
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: The data quality did not permit refinement of anistropic displacement
parmeters. This CIF is a supplementary one to the as-synthesized
material.
;
_vrf_PLAT082_1EtOH_stored        
;
PROBLEM: High R1 Value ..................................       0.31 Report
RESPONSE: The R-values of electron diffraction data are usually higher than
expected due to dynamical effects (multiple scattering).
;
_vrf_PLAT084_1EtOH_stored        
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.69 Report
RESPONSE: The R-values of electron diffraction data are usually higher than
expected due to dynamical effects (multiple scattering).
;
_vrf_PLAT201_1EtOH_stored        
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         16 Report
RESPONSE: The data quality did not permit refinement of anistropic displacement
parmeters. This CIF is just a supplementary one to the as-synthesized
material.
;
_vrf_PLAT241_1EtOH_stored        
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         O6 Check
RESPONSE: O6 is part of a coordinated ethanol molecule, and is likely more
prone to displacement in relation to its neighbour (Bi1).
;
_vrf_PLAT242_1EtOH_stored        
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        Bi1 Check
RESPONSE: This error likely arises due to the comparitively large displacement
parameters of the atoms belonging to the coordinated ethanol molecule.
;
_vrf_PLAT413_1EtOH_stored        
;
PROBLEM: Short Inter XH3 .. XHn     H7       ..H9A      .       1.85 Ang.
RESPONSE: H9X hydrogens are part of a likely rotationally averaged methyl group
on the coordinated ethanol molecule.
;
_vrf_PLAT420_1EtOH_stored        
;
PROBLEM: D-H Bond Without Acceptor  O5       --H5       .     Please Check
RESPONSE: The assigned protonation would give a charge-balanced material, and is
in line with the more high-quality refinement made of the as-synthesized
material.
;
_vrf_PLAT430_1EtOH_stored        
;
PROBLEM: Short Inter D...A Contact  O3       ..O4       .       2.58 Ang.
RESPONSE: The two oxygens O3 and O4 bridge the bismuth cations in the structure.
;
_vrf_PLAT936_1EtOH_stored        
;
PROBLEM: The Embedded .res File Includes a DAMP Command .     1000.0 Report
RESPONSE: We chose to leave the DAMP command as the structure was somewhat
unstable without it. This CIF is a supplementary one to the as-synthesized
material, showing the material in a slightly different state.
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1EtOH
_database_code_depnum_ccdc_archive 'CCDC 2183352'
loop_
_audit_author_name
_audit_author_address
'Erik Svensson Grape'
;Stockholm University
Sweden
;
_audit_update_record             
;
2022-08-16 deposited with the CCDC.	2022-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 Bi O6'
_chemical_formula_weight         422.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   7.89(4)
_cell_length_b                   8.61(4)
_cell_length_c                   17.38(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1181(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16554
_cell_measurement_theta_min      0.083
_cell_measurement_theta_max      0.898

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.375
_exptl_crystal_F_000             209
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.000
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.0251
_diffrn_radiation_type           electron
_diffrn_source                   ?
_diffrn_measurement_device_type  'JEOL JEM-2100 LaB6'
_diffrn_measurement_method       'continuous rotation'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16554
_diffrn_reflns_av_unetI/netI     0.1234
_diffrn_reflns_av_R_equivalents  0.2110
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         0.083
_diffrn_reflns_theta_max         0.898
_diffrn_reflns_theta_full        0.863
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2396
_reflns_number_gt                2337
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.999

_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       
;
Stef Smeets, Bin Wang, Magdalena O. Cichocka, Jonas Angstrom, Wei Wan.
(2018, April 11). Instamatic (Version 0.6). Zenodo.
http://doi.org/10.5281/zenodo.1217026
;
_computing_cell_refinement       
;
Kabsch, W. (2010). XDS. Acta Crystallographica Section D:
Biological Crystallography, 66(2), 125-132.
;
_computing_data_reduction        
;
Kabsch, W. (2010). XDS. Acta Crystallographica Section D:
Biological Crystallography, 66(2), 125-132.
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1173P)²+1.4141P] 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_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2396
_refine_ls_number_parameters     147
_refine_ls_number_restraints     168
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.1409
_refine_ls_wR_factor_ref         0.3442
_refine_ls_wR_factor_gt          0.3432
_refine_ls_goodness_of_fit_ref   1.281
_refine_ls_restrained_S_all      1.250
_refine_ls_shift/su_max          0.000
_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 0.3364(3) 0.2921(3) 0.46771(13) 0.0204(13) Uani 1 1 d . U . . .
O1 O 0.230(3) -0.088(3) 0.8902(11) 0.048(5) Uani 1 1 d . U . . .
O2 O -0.023(3) -0.050(3) 0.8206(13) 0.056(5) Uani 1 1 d . U . . .
O3 O 0.1811(17) 0.1736(18) 0.5536(8) 0.0221(17) Uani 1 1 d . U . . .
O4 O 0.5282(17) 0.153(2) 0.5525(8) 0.0221(17) Uani 1 1 d . U . . .
O5 O 0.7032(18) 0.024(2) 0.6811(9) 0.026(2) Uani 1 1 d . U . . .
H5 H 0.739462 -0.017059 0.720310 0.040 Uiso 1 1 calc R U . . .
O6 O 0.292(4) 0.498(3) 0.5794(13) 0.062(6) Uani 1 1 d . U . . .
H6 H 0.244525 0.461167 0.624933 0.075 Uiso 1 1 calc R U . . .
C1 C 0.146(3) -0.046(3) 0.8256(13) 0.041(6) Uani 1 1 d . . . . .
C2 C 0.248(3) 0.001(3) 0.7537(12) 0.037(6) Uani 1 1 d . . . . .
C3 C 0.169(2) 0.058(2) 0.6865(10) 0.0233(18) Uani 1 1 d . U . . .
H3 H 0.051397 0.062758 0.685831 0.028 Uiso 1 1 calc R U . . .
C4 C 0.256(2) 0.107(3) 0.6210(11) 0.0225(17) Uani 1 1 d . U . . .
C5 C 0.433(2) 0.105(3) 0.6192(11) 0.0228(16) Uani 1 1 d . U . . .
C6 C 0.533(2) 0.036(3) 0.6854(10) 0.0230(18) Uani 1 1 d . U . . .
C7 C 0.431(2) -0.009(3) 0.7551(11) 0.0234(18) Uani 1 1 d . U . . .
H7 H 0.486434 -0.043427 0.799237 0.028 Uiso 1 1 calc R U . . .
C8 C 0.335(5) 0.663(4) 0.5764(17) 0.076(7) Uani 1 1 d . U . . .
H8A H 0.412790 0.687931 0.617793 0.091 Uiso 1 1 calc R U . . .
H8B H 0.232955 0.724506 0.583596 0.091 Uiso 1 1 calc R U . . .
C9 C 0.415(6) 0.705(5) 0.500(2) 0.112(11) Uani 1 1 d . U . . .
H9A H 0.442365 0.813404 0.499452 0.168 Uiso 1 1 calc R U . . .
H9B H 0.517274 0.645264 0.493285 0.168 Uiso 1 1 calc R U . . .
H9C H 0.337693 0.681788 0.459137 0.168 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 O3 2.184(16) . ?
Bi1 O1 2.28(2) 2_554 ?
Bi1 O4 2.429(16) . ?
Bi1 O4 2.501(18) 4_456 ?
Bi1 O6 2.65(2) . ?
O1 C1 1.36(3) . ?
O2 C1 1.34(3) . ?
O3 C4 1.43(2) . ?
O4 C5 1.44(2) . ?
O5 C6 1.35(3) . ?
O5 H5 0.8200 . ?
O6 C8 1.47(4) . ?
O6 H6 0.9300 . ?
C1 C2 1.54(3) . ?
C2 C3 1.41(3) . ?
C2 C7 1.45(3) . ?
C3 C4 1.40(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.39(2) . ?
C5 C6 1.52(3) . ?
C6 C7 1.50(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.51(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Bi1 O1 85.1(8) . 2_554 ?
O3 Bi1 O4 72.8(6) . . ?
O1 Bi1 O4 97.0(8) 2_554 . ?
O3 Bi1 O4 68.9(5) . 4_456 ?
O1 Bi1 O4 80.7(7) 2_554 4_456 ?
O4 Bi1 O4 141.6(4) . 4_456 ?
O3 Bi1 O6 74.8(8) . . ?
O1 Bi1 O6 156.7(8) 2_554 . ?
O4 Bi1 O6 88.1(8) . . ?
O4 Bi1 O6 81.3(7) 4_456 . ?
C1 O1 Bi1 125.8(18) . 2 ?
C4 O3 Bi1 120.9(11) . . ?
C5 O4 Bi1 107.7(11) . . ?
C5 O4 Bi1 132.4(11) . 4_556 ?
Bi1 O4 Bi1 115.3(6) . 4_556 ?
C6 O5 H5 109.5 . . ?
C8 O6 Bi1 126.3(19) . . ?
C8 O6 H6 116.8 . . ?
Bi1 O6 H6 116.8 . . ?
O2 C1 O1 123(2) . . ?
O2 C1 C2 118(2) . . ?
O1 C1 C2 119(2) . . ?
C3 C2 C7 118(2) . . ?
C3 C2 C1 122.3(19) . . ?
C7 C2 C1 119(2) . . ?
C4 C3 C2 124.4(19) . . ?
C4 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
C5 C4 C3 120.5(19) . . ?
C5 C4 O3 113.6(18) . . ?
C3 C4 O3 125.8(16) . . ?
C4 C5 O4 122.5(18) . . ?
C4 C5 C6 120.6(19) . . ?
O4 C5 C6 116.6(15) . . ?
O5 C6 C7 123.8(16) . . ?
O5 C6 C5 120.4(16) . . ?
C7 C6 C5 115.7(16) . . ?
C2 C7 C6 120.2(19) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
O6 C8 C9 111(3) . . ?
O6 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
O6 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         0.521
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.094



# start Validation Reply Form
_vrf_RINTA01_1EtOH               
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The R-values of electron diffraction data are usually higher than
expected due to dynamical effects (multiple scattering).
;
_vrf_PLAT020_1EtOH               
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.211 Report
RESPONSE: The R-values of electron diffraction data are usually higher than
expected due to dynamical effects (multiple scattering).
;
_vrf_PLAT342_1EtOH               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03125 Ang.
RESPONSE: The uncertainty in unit cell parameters determined from 3DED largely
contribute to this low precision.
;
# end Validation Reply Form
