# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_20190920zh_znz4046_2_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 1998943'
loop_
_audit_author_name
_audit_author_address
'Xurui Zhang'
;Shanghai university
China
;
_audit_update_record             
;
2020-04-24 deposited with the CCDC.	2020-04-24 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         ?
_chemical_formula_sum            'C12 H10 Bi N O7'
_chemical_formula_weight         489.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 -4.3533 7.1873 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   10.1416(3)
_cell_length_b                   14.7630(4)
_cell_length_c                   11.3618(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.1670(10)
_cell_angle_gamma                90
_cell_volume                     1674.38(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      4.69
_cell_measurement_theta_max      53.96

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.941
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    13.954
_shelx_estimated_absorpt_T_min   0.264
_shelx_estimated_absorpt_T_max   0.401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1821
_exptl_absorpt_correction_T_max  0.3667
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13110
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.691
_diffrn_reflns_theta_max         52.994
_diffrn_reflns_theta_full        52.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2943
_reflns_number_gt                2790
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (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)+(0.0308P)²+8.4084P] 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         2943
_refine_ls_number_parameters     192
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.080
_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 0.39278(2) 0.54864(2) 0.60411(2) 0.01980(10) Uani 1 1 d . . . . .
C1 C 0.6724(5) 0.5824(4) 0.6858(5) 0.0230(12) Uani 1 1 d . . . . .
C2 C 0.8045(5) 0.6262(4) 0.7262(5) 0.0227(11) Uani 1 1 d . . . . .
C3 C 0.9151(5) 0.5963(4) 0.6797(5) 0.0262(12) Uani 1 1 d . . . . .
H3 H 0.906209 0.548013 0.623596 0.031 Uiso 1 1 calc R U . . .
C4 C 1.0397(5) 0.6383(4) 0.7163(5) 0.0231(12) Uani 1 1 d . . . . .
C5 C 1.0516(5) 0.7087(4) 0.7980(5) 0.0247(12) Uani 1 1 d . . . . .
H5 H 1.136126 0.736981 0.822638 0.030 Uiso 1 1 calc R U . . .
C6 C 0.9415(5) 0.7382(4) 0.8441(5) 0.0227(11) Uani 1 1 d . . . . .
C7 C 0.8187(5) 0.6967(4) 0.8075(5) 0.0255(12) Uani 1 1 d . . . . .
H7 H 0.742929 0.717080 0.838720 0.031 Uiso 1 1 calc R U . . .
C8 C 1.1581(6) 0.6045(4) 0.6678(5) 0.0277(13) Uani 1 1 d . . . . .
C9 C 0.9532(5) 0.8144(4) 0.9332(5) 0.0231(11) Uani 1 1 d . . . . .
C10 C 0.6405(18) 0.3335(13) 0.9837(16) 0.161(6) Uani 1 1 d . U . . .
H10A H 0.711352 0.365614 0.952101 0.241 Uiso 1 1 calc R U . . .
H10B H 0.641685 0.269298 0.961878 0.241 Uiso 1 1 calc R U . . .
H10C H 0.655785 0.339275 1.070958 0.241 Uiso 1 1 calc R U . . .
C11 C 0.399(2) 0.3466(15) 0.9803(18) 0.186(8) Uani 1 1 d . U . . .
H11A H 0.365991 0.398553 1.020278 0.278 Uiso 1 1 calc R U . . .
H11B H 0.422624 0.297368 1.038029 0.278 Uiso 1 1 calc R U . . .
H11C H 0.328829 0.325848 0.915182 0.278 Uiso 1 1 calc R U . . .
C12 C 0.5022(14) 0.4328(8) 0.8411(11) 0.089(3) Uani 1 1 d . U . . .
H12 H 0.583320 0.443367 0.812505 0.107 Uiso 1 1 calc R U . . .
N1 N 0.5120(11) 0.3722(7) 0.9337(9) 0.096(3) Uani 1 1 d . U . . .
O1 O 0.6636(4) 0.5080(3) 0.6330(4) 0.0257(8) Uani 1 1 d . . . . .
O2 O 0.5684(3) 0.6254(3) 0.7090(4) 0.0283(9) Uani 1 1 d . . . . .
O3 O 0.8570(4) 0.8225(3) 0.9918(4) 0.0284(9) Uani 1 1 d . . . . .
O4 O 1.0522(4) 0.8652(2) 0.9456(4) 0.0271(9) Uani 1 1 d . . . . .
O5 O 1.2739(3) 0.6342(3) 0.7127(3) 0.0258(9) Uani 1 1 d . . . . .
O6 O 1.1453(5) 0.5447(3) 0.5886(5) 0.0507(15) Uani 1 1 d . . . . .
O7 O 0.4147(8) 0.4713(4) 0.7944(5) 0.0685(19) 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 O5 2.257(4) 1_455 ?
Bi1 O2 2.264(4) . ?
Bi1 O3 2.284(4) 4_575 ?
Bi1 O7 2.421(5) . ?
Bi1 O6 2.485(5) 1_455 ?
Bi1 C8 2.734(6) 1_455 ?
Bi1 C1 2.868(5) . ?
C1 O1 1.247(7) . ?
C1 O2 1.297(7) . ?
C1 C2 1.485(7) . ?
C2 C7 1.382(8) . ?
C2 C3 1.393(8) . ?
C3 C4 1.402(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(8) . ?
C4 C8 1.493(7) . ?
C5 C6 1.385(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(8) . ?
C6 C9 1.503(8) . ?
C7 H7 0.9500 . ?
C8 O6 1.251(7) . ?
C8 O5 1.273(7) . ?
C9 O4 1.241(6) . ?
C9 O3 1.281(7) . ?
C10 N1 1.444(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N1 1.397(19) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O7 1.107(13) . ?
C12 N1 1.371(14) . ?
C12 H12 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
O5 Bi1 O2 83.02(13) 1_455 . ?
O5 Bi1 O3 77.98(14) 1_455 4_575 ?
O2 Bi1 O3 84.83(15) . 4_575 ?
O5 Bi1 O7 75.48(17) 1_455 . ?
O2 Bi1 O7 80.0(2) . . ?
O3 Bi1 O7 150.75(18) 4_575 . ?
O5 Bi1 O6 54.69(14) 1_455 1_455 ?
O2 Bi1 O6 137.70(14) . 1_455 ?
O3 Bi1 O6 85.47(17) 4_575 1_455 ?
O7 Bi1 O6 89.1(2) . 1_455 ?
O5 Bi1 C8 27.49(15) 1_455 1_455 ?
O2 Bi1 C8 110.51(15) . 1_455 ?
O3 Bi1 C8 80.60(16) 4_575 1_455 ?
O7 Bi1 C8 81.5(2) . 1_455 ?
O6 Bi1 C8 27.20(16) 1_455 1_455 ?
O5 Bi1 C1 108.57(14) 1_455 . ?
O2 Bi1 C1 26.04(15) . . ?
O3 Bi1 C1 94.96(15) 4_575 . ?
O7 Bi1 C1 82.1(2) . . ?
O6 Bi1 C1 162.85(16) 1_455 . ?
C8 Bi1 C1 135.98(16) 1_455 . ?
O1 C1 O2 122.4(5) . . ?
O1 C1 C2 121.0(5) . . ?
O2 C1 C2 116.5(5) . . ?
O1 C1 Bi1 73.0(3) . . ?
O2 C1 Bi1 50.0(3) . . ?
C2 C1 Bi1 164.2(4) . . ?
C7 C2 C3 119.8(5) . . ?
C7 C2 C1 121.0(5) . . ?
C3 C2 C1 119.2(5) . . ?
C2 C3 C4 119.4(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.9(5) . . ?
C5 C4 C8 121.1(5) . . ?
C3 C4 C8 119.0(5) . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 119.3(5) . . ?
C5 C6 C9 121.1(5) . . ?
C7 C6 C9 119.5(5) . . ?
C2 C7 C6 121.1(5) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
O6 C8 O5 120.2(5) . . ?
O6 C8 C4 120.9(5) . . ?
O5 C8 C4 118.9(5) . . ?
O6 C8 Bi1 65.2(3) . 1_655 ?
O5 C8 Bi1 54.9(3) . 1_655 ?
C4 C8 Bi1 173.3(4) . 1_655 ?
O4 C9 O3 124.0(5) . . ?
O4 C9 C6 119.7(5) . . ?
O3 C9 C6 116.3(5) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O7 C12 N1 130.3(13) . . ?
O7 C12 H12 114.8 . . ?
N1 C12 H12 114.8 . . ?
C12 N1 C11 120.9(14) . . ?
C12 N1 C10 119.9(13) . . ?
C11 N1 C10 119.2(14) . . ?
C1 O2 Bi1 104.0(3) . . ?
C9 O3 Bi1 107.9(3) . 4_676 ?
C8 O5 Bi1 97.6(3) . 1_655 ?
C8 O6 Bi1 87.6(3) . 1_655 ?
C12 O7 Bi1 127.6(8) . . ?

_refine_diff_density_max         1.805
_refine_diff_density_min         -1.166
_refine_diff_density_rms         0.151



