# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_cd1005c-jana_sq
_database_code_depnum_ccdc_archive 'CCDC 1964916'
loop_
_audit_author_name
_audit_author_address
'Jing Zhao'
;University of Science and Technology Beijing
China
;
_audit_update_record             
;
2019-11-10 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H29 Bi Br6 N3'
_chemical_formula_weight         1011.91

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.425
_cell_length_b                   8.174
_cell_length_c                   24.610
_cell_angle_alpha                90.00
_cell_angle_beta                 99.56
_cell_angle_gamma                90.00
_cell_volume                     3059.6
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4964
_cell_measurement_theta_min      2.2860
_cell_measurement_theta_max      24.6330

_exptl_crystal_description       bulk
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.0340
_exptl_crystal_size_mid          0.0190
_exptl_crystal_size_min          0.0145
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1876
_exptl_absorpt_coefficient_mu    13.612
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.00084
_exptl_absorpt_correction_T_max  0.00851
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25982
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5375
_reflns_number_gt                4085
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1215P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5375
_refine_ls_number_parameters     283
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0801
_refine_ls_wR_factor_ref         0.2023
_refine_ls_wR_factor_gt          0.1869
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.129
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.63914(2) 0.49863(4) 0.147040(14) 0.06476(11) Uani 1 1 d . . .
Br1 Br 0.79968(7) 0.42571(14) 0.10173(5) 0.0850(3) Uani 1 1 d . . .
Br2 Br 0.67366(9) 0.24062(13) 0.22419(4) 0.0865(3) Uani 1 1 d . . .
Br3 Br 0.55363(8) 0.27862(15) 0.06561(5) 0.0883(3) Uani 1 1 d . . .
Br4 Br 0.60218(8) 0.77087(13) 0.06954(4) 0.0810(3) Uani 1 1 d . . .
Br5 Br 0.70697(7) 0.74362(13) 0.22744(4) 0.0781(3) Uani 1 1 d . . .
Br6 Br 0.47049(8) 0.54269(16) 0.17743(5) 0.0911(3) Uani 1 1 d . . .
N1 N 1.4978(8) 0.9572(13) 0.1784(5) 0.118(4) Uani 1 1 d . . .
H1A H 1.5300 0.9764 0.1523 0.142 Uiso 1 1 calc R . .
H1B H 1.4865 0.8506 0.1796 0.142 Uiso 1 1 calc R . .
H1C H 1.5271 0.9895 0.2108 0.142 Uiso 1 1 calc R . .
C1 C 1.4208(9) 1.0415(16) 0.1668(6) 0.099(4) Uani 1 1 d . . .
H1D H 1.4344 1.1530 0.1577 0.119 Uiso 1 1 calc R . .
H1E H 1.3950 1.0459 0.2002 0.119 Uiso 1 1 calc R . .
C2 C 1.3524(8) 0.9771(11) 0.1213(5) 0.079(3) Uani 1 1 d D . .
C3 C 1.2668(9) 0.9521(15) 0.1329(5) 0.094(4) Uani 1 1 d D . .
C4 C 1.2008(9) 0.8975(14) 0.0911(5) 0.104(4) Uani 1 1 d D . .
H4 H 1.1443 0.8813 0.0986 0.124 Uiso 1 1 calc R . .
C5 C 1.2184(8) 0.8672(12) 0.0390(5) 0.090(3) Uani 1 1 d D . .
H5 H 1.1740 0.8290 0.0117 0.108 Uiso 1 1 calc R . .
C6 C 1.3015(8) 0.8932(11) 0.0269(4) 0.080(3) Uani 1 1 d D . .
C7 C 1.3693(8) 0.9534(12) 0.0674(5) 0.080(3) Uani 1 1 d D . .
N2 N 1.3487(8) 1.4974(11) 0.0383(5) 0.100(3) Uani 1 1 d . . .
H2A H 1.3423 1.5865 0.0581 0.120 Uiso 1 1 calc R . .
H2B H 1.3304 1.5185 0.0028 0.120 Uiso 1 1 calc R . .
H2C H 1.4051 1.4685 0.0435 0.120 Uiso 1 1 calc R . .
C8 C 1.2961(9) 1.3630(15) 0.0560(6) 0.107(4) Uani 1 1 d U . .
H8A H 1.3332 1.3008 0.0844 0.128 Uiso 1 1 calc R . .
H8B H 1.2789 1.2905 0.0248 0.128 Uiso 1 1 calc R . .
C9 C 1.2144(8) 1.4135(13) 0.0778(5) 0.085(3) Uani 1 1 d DU . .
C10 C 1.1348(9) 1.401(2) 0.0467(6) 0.117(5) Uani 1 1 d D . .
H10 H 1.1297 1.3644 0.0105 0.141 Uiso 1 1 calc R . .
C11 C 1.0607(10) 1.4411(16) 0.0679(6) 0.117(5) Uani 1 1 d D . .
C12 C 1.0669(11) 1.4960(13) 0.1212(7) 0.123(5) Uani 1 1 d D . .
H12 H 1.0165 1.5236 0.1353 0.147 Uiso 1 1 calc R . .
C13 C 1.1491(9) 1.5098(14) 0.1537(7) 0.115(6) Uani 1 1 d D . .
H13 H 1.1553 1.5463 0.1899 0.138 Uiso 1 1 calc R . .
C14 C 1.2222(8) 1.4672(15) 0.1302(6) 0.096(4) Uani 1 1 d D . .
H14 H 1.2779 1.4760 0.1513 0.115 Uiso 1 1 calc R . .
N3 N 0.7677(6) 1.0103(10) 0.1330(4) 0.085(3) Uani 1 1 d . . .
H3A H 0.7173 0.9961 0.1100 0.102 Uiso 1 1 calc R . .
H3B H 0.7811 1.1163 0.1351 0.102 Uiso 1 1 calc R . .
H3C H 0.7619 0.9736 0.1663 0.102 Uiso 1 1 calc R . .
C15 C 0.8365(7) 0.9215(15) 0.1133(4) 0.086(3) Uani 1 1 d . . .
H15A H 0.8420 0.9615 0.0769 0.103 Uiso 1 1 calc R . .
H15B H 0.8204 0.8068 0.1098 0.103 Uiso 1 1 calc R . .
C16 C 0.9258(7) 0.9372(13) 0.1510(4) 0.081(3) Uani 1 1 d D . .
C17 C 0.9862(8) 1.0650(15) 0.1433(5) 0.097(4) Uani 1 1 d D . .
H17 H 0.9719 1.1395 0.1147 0.116 Uiso 1 1 calc R . .
C18 C 1.0644(8) 1.0772(17) 0.1779(7) 0.110(4) Uani 1 1 d D . .
H18 H 1.1046 1.1579 0.1725 0.132 Uiso 1 1 calc R . .
C19 C 1.0838(10) 0.9670(16) 0.2217(6) 0.105(4) Uani 1 1 d D . .
H19 H 1.1367 0.9759 0.2459 0.126 Uiso 1 1 calc R . .
C20 C 1.0273(9) 0.8501(18) 0.2290(6) 0.111(4) Uani 1 1 d D . .
H20 H 1.0413 0.7785 0.2585 0.134 Uiso 1 1 calc R . .
C21 C 0.9478(8) 0.8316(15) 0.1939(5) 0.101(4) Uani 1 1 d D . .
H21 H 0.9098 0.7474 0.1995 0.122 Uiso 1 1 calc R . .


_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 Br2 2.8284(11) . ?
Bi1 Br6 2.8465(12) . ?
Bi1 Br3 2.8480(11) . ?
Bi1 Br5 2.8866(10) . ?
Bi1 Br4 2.9246(11) . ?
Bi1 Br1 2.9408(11) . ?
N1 C1 1.362(16) . ?
C1 C2 1.502(17) . ?
C2 C7 1.407(16) . ?
C2 C3 1.411(17) . ?
C3 C4 1.395(17) . ?
C4 C5 1.377(16) . ?
C5 C6 1.379(16) . ?
C6 C7 1.408(15) . ?
N2 C8 1.473(16) . ?
C8 C9 1.508(17) . ?
C9 C10 1.339(17) . ?
C9 C14 1.348(17) . ?
C10 C11 1.37(2) . ?
C11 C12 1.38(2) . ?
C12 C13 1.39(2) . ?
C13 C14 1.392(19) . ?
N3 C15 1.436(14) . ?
C15 C16 1.534(15) . ?
C16 C21 1.361(16) . ?
C16 C17 1.433(16) . ?
C17 C18 1.360(18) . ?
C18 C19 1.40(2) . ?
C19 C20 1.326(19) . ?
C20 C21 1.386(17) . ?

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
Br2 Bi1 Br6 89.78(4) . . ?
Br2 Bi1 Br3 90.87(4) . . ?
Br6 Bi1 Br3 85.88(4) . . ?
Br2 Bi1 Br5 92.91(3) . . ?
Br6 Bi1 Br5 88.57(3) . . ?
Br3 Bi1 Br5 173.28(4) . . ?
Br2 Bi1 Br4 178.50(3) . . ?
Br6 Bi1 Br4 89.28(4) . . ?
Br3 Bi1 Br4 90.24(3) . . ?
Br5 Bi1 Br4 85.90(3) . . ?
Br2 Bi1 Br1 91.55(4) . . ?
Br6 Bi1 Br1 171.55(4) . . ?
Br3 Bi1 Br1 85.75(3) . . ?
Br5 Bi1 Br1 99.69(3) . . ?
Br4 Bi1 Br1 89.54(3) . . ?
N1 C1 C2 117.3(11) . . ?
C7 C2 C3 119.8(11) . . ?
C7 C2 C1 122.3(11) . . ?
C3 C2 C1 117.6(11) . . ?
C4 C3 C2 119.3(11) . . ?
C5 C4 C3 120.8(12) . . ?
C4 C5 C6 120.5(11) . . ?
C5 C6 C7 120.6(10) . . ?
C2 C7 C6 118.9(11) . . ?
N2 C8 C9 115.7(10) . . ?
C10 C9 C14 120.0(13) . . ?
C10 C9 C8 121.0(12) . . ?
C14 C9 C8 118.9(11) . . ?
C9 C10 C11 120.4(13) . . ?
C10 C11 C12 120.7(14) . . ?
C11 C12 C13 119.2(15) . . ?
C12 C13 C14 117.8(15) . . ?
C9 C14 C13 121.9(12) . . ?
N3 C15 C16 113.1(9) . . ?
C21 C16 C17 118.7(10) . . ?
C21 C16 C15 120.0(10) . . ?
C17 C16 C15 121.2(10) . . ?
C18 C17 C16 119.9(12) . . ?
C17 C18 C19 119.3(13) . . ?
C20 C19 C18 120.5(13) . . ?
C19 C20 C21 121.9(13) . . ?
C16 C21 C20 119.7(12) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.770
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.331
####################################################################### 
# 
# 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_2019zj003
_database_code_depnum_ccdc_archive 'CCDC 1964917'
loop_
_audit_author_name
_audit_author_address
'Jing Zhao'
;University of Science and Technology Beijing
China
;
_audit_update_record             
;
2019-11-10 deposited with the CCDC.	2020-03-18 downloaded from the CCDC.
;
_audit_creation_date             2019-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br6 Sb, 3(C7 H10 N)'
_chemical_formula_sum            'C21 H30 Br6 N3 Sb'
_chemical_formula_weight         925.69
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.2246(3)
_cell_length_b                   8.0632(2)
_cell_length_c                   24.3042(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.005(2)
_cell_angle_gamma                90
_cell_volume                     2938.19(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13306
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.6050
_cell_measurement_theta_min      2.3160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  1.00000
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bulk
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.0320
_exptl_crystal_size_mid          0.0190
_exptl_crystal_size_min          0.0145
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            35727
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.346
_diffrn_reflns_theta_min         1.984
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5791
_reflns_number_total             7296
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         7296
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.239
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0190P)²+4.1657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0593
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2. Restrained distances
 C3-C4 \\sim C5-C7 \\sim C6-C2
 with sigma of 0.02
 C13-C12 \\sim C11-C10 \\sim C9-C14
 with sigma of 0.02
 C17-C16 \\sim C18-C19 \\sim C21-C20
 with sigma of 0.02
3. Restrained planarity
 C4, C3, C2, C6, C5, C7
 with sigma of 0.1
 C12, C13, C14, C9, C10, C11
 with sigma of 0.1
 C16, C17, C18, C19, C20, C21
 with sigma of 0.1
4.a Secondary CH2 refined with riding coordinates:
 C1(H1D,H1E), C8(H8A,H8B), C15(H15A,H15B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
4.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2A,H2B,H2C), N3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.63694(2) 0.50310(2) 0.64758(2) 0.02663(5) Uani 1 1 d . . . . .
Br1 Br 0.70498(2) 0.25839(4) 0.72729(2) 0.03765(8) Uani 1 1 d . . . . .
Br2 Br 0.59851(2) 0.23364(4) 0.56943(2) 0.04036(9) Uani 1 1 d . . . . .
Br3 Br 0.55363(2) 0.72198(5) 0.56818(2) 0.04418(9) Uani 1 1 d . . . . .
Br4 Br 0.79851(2) 0.57686(4) 0.60177(2) 0.04188(9) Uani 1 1 d . . . . .
Br5 Br 0.67110(3) 0.75495(4) 0.72400(2) 0.04516(9) Uani 1 1 d . . . . .
Br6 Br 0.47344(2) 0.46029(5) 0.67737(2) 0.04798(10) Uani 1 1 d . . . . .
N1 N 0.3442(2) 0.5031(4) 0.53279(14) 0.0533(8) Uani 1 1 d . . . . .
H1A H 0.308980 0.456940 0.503787 0.064 Uiso 1 1 calc GR . . . .
H1B H 0.359317 0.427493 0.559427 0.064 Uiso 1 1 calc GR . . . .
H1C H 0.393179 0.542045 0.521939 0.064 Uiso 1 1 calc GR . . . .
C1 C 0.2964(3) 0.6405(5) 0.55472(19) 0.0588(11) Uani 1 1 d . . . . .
H1D H 0.278102 0.719729 0.524892 0.071 Uiso 1 1 calc R . . . .
H1E H 0.337319 0.696743 0.583847 0.071 Uiso 1 1 calc R . . . .
C2 C 0.2150(2) 0.5872(4) 0.57825(15) 0.0417(8) Uani 1 1 d D . . . .
C3 C 0.1338(3) 0.6053(6) 0.54560(18) 0.0650(12) Uani 1 1 d D . . . .
H3 H 0.127830 0.645788 0.509311 0.078 Uiso 1 1 calc R . . . .
C4 C 0.0540(3) 0.5570(6) 0.5706(2) 0.0747(15) Uani 1 1 d D . . . .
H4 H -0.003447 0.565637 0.550138 0.090 Uiso 1 1 calc R . . . .
C5 C 0.0681(3) 0.5017(6) 0.6227(2) 0.0689(13) Uani 1 1 d D . . . .
H5 H 0.019429 0.471211 0.638811 0.083 Uiso 1 1 calc R . . . .
C6 C 0.1498(3) 0.4883(6) 0.65282(19) 0.0664(12) Uani 1 1 d D . . . .
H6 H 0.156867 0.449033 0.689302 0.080 Uiso 1 1 calc R . . . .
C7 C 0.2220(3) 0.5308(5) 0.63120(17) 0.0543(10) Uani 1 1 d D . . . .
H7 H 0.278230 0.521147 0.653182 0.065 Uiso 1 1 calc R . . . .
N2 N 0.5021(2) 0.0433(5) 0.67551(16) 0.0732(12) Uani 1 1 d . . . . .
H2A H 0.524004 0.047944 0.643910 0.088 Uiso 1 1 calc GR . . . .
H2B H 0.540718 -0.008393 0.701588 0.088 Uiso 1 1 calc GR . . . .
H2C H 0.492798 0.145678 0.686924 0.088 Uiso 1 1 calc GR . . . .
C8 C 0.4197(3) -0.0455(5) 0.66607(17) 0.0530(10) Uani 1 1 d . . . . .
H8A H 0.395750 -0.046625 0.700520 0.064 Uiso 1 1 calc R . . . .
H8B H 0.431701 -0.159518 0.656992 0.064 Uiso 1 1 calc R . . . .
C9 C 0.3500(2) 0.0232(4) 0.62037(13) 0.0349(7) Uani 1 1 d D . . . .
C10 C 0.3659(2) 0.0520(4) 0.56672(14) 0.0382(8) Uani 1 1 d D . . . .
H10 H 0.422547 0.034685 0.558471 0.046 Uiso 1 1 calc R . . . .
C11 C 0.2977(2) 0.1064(4) 0.52532(14) 0.0420(8) Uani 1 1 d D . . . .
H11 H 0.308810 0.124686 0.489380 0.050 Uiso 1 1 calc R . . . .
C12 C 0.2140(3) 0.1335(5) 0.53698(16) 0.0481(9) Uani 1 1 d D . . . .
H12 H 0.168418 0.170672 0.509177 0.058 Uiso 1 1 calc R . . . .
C13 C 0.1979(3) 0.1051(5) 0.59034(16) 0.0556(10) Uani 1 1 d D . . . .
H13 H 0.141221 0.123148 0.598505 0.067 Uiso 1 1 calc R . . . .
C14 C 0.2656(2) 0.0499(5) 0.63175(15) 0.0474(9) Uani 1 1 d D . . . .
H14 H 0.254038 0.030576 0.667536 0.057 Uiso 1 1 calc R . . . .
N3 N 0.76486(19) -0.0116(3) 0.63295(12) 0.0428(7) Uani 1 1 d . . . . .
H3A H 0.712745 0.008543 0.611067 0.051 Uiso 1 1 calc GR . . . .
H3B H 0.762029 0.018695 0.667814 0.051 Uiso 1 1 calc GR . . . .
H3C H 0.777068 -0.119429 0.632168 0.051 Uiso 1 1 calc GR . . . .
C15 C 0.8363(2) 0.0844(5) 0.61256(15) 0.0450(9) Uani 1 1 d . . . . .
H15A H 0.819977 0.200758 0.609999 0.054 Uiso 1 1 calc R . . . .
H15B H 0.841693 0.046366 0.575425 0.054 Uiso 1 1 calc R . . . .
C16 C 0.9243(2) 0.0654(4) 0.65052(15) 0.0389(8) Uani 1 1 d D . . . .
C17 C 0.9470(3) 0.1715(5) 0.69505(17) 0.0564(11) Uani 1 1 d D . . . .
H17 H 0.907785 0.255083 0.701290 0.068 Uiso 1 1 calc R . . . .
C18 C 1.0282(3) 0.1540(6) 0.73072(19) 0.0648(12) Uani 1 1 d D . . . .
H18 H 1.042787 0.225330 0.761005 0.078 Uiso 1 1 calc R . . . .
C19 C 1.0864(3) 0.0338(5) 0.72174(19) 0.0560(11) Uani 1 1 d D . . . .
H19 H 1.141086 0.024024 0.745425 0.067 Uiso 1 1 calc R . . . .
C20 C 1.0645(3) -0.0726(5) 0.6779(2) 0.0596(11) Uani 1 1 d D . . . .
H20 H 1.104071 -0.156070 0.672098 0.072 Uiso 1 1 calc R . . . .
C21 C 0.9840(3) -0.0571(5) 0.64222(17) 0.0504(10) Uani 1 1 d D . . . .
H21 H 0.969874 -0.129689 0.612270 0.060 Uiso 1 1 calc R . . . .


_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
Sb1 Br1 2.8324(4) . ?
Sb1 Br2 2.8784(4) . ?
Sb1 Br3 2.7563(4) . ?
Sb1 Br4 2.9319(4) . ?
Sb1 Br5 2.7401(4) . ?
Sb1 Br6 2.7323(4) . ?
N1 C1 1.475(5) . ?
C1 C2 1.516(5) . ?
C2 C3 1.355(5) . ?
C2 C7 1.352(5) . ?
C3 C4 1.501(6) . ?
C4 C5 1.325(7) . ?
C5 C6 1.334(6) . ?
C6 C7 1.343(5) . ?
N2 C8 1.427(5) . ?
C8 C9 1.503(5) . ?
C9 C10 1.386(5) . ?
C9 C14 1.378(5) . ?
C10 C11 1.385(5) . ?
C11 C12 1.370(5) . ?
C12 C13 1.380(5) . ?
C13 C14 1.383(5) . ?
N3 C15 1.488(4) . ?
C15 C16 1.496(5) . ?
C16 C17 1.375(5) . ?
C16 C21 1.382(5) . ?
C17 C18 1.388(6) . ?
C18 C19 1.356(5) . ?
C19 C20 1.363(6) . ?
C20 C21 1.379(5) . ?

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
Br1 Sb1 Br2 86.201(11) . . ?
Br1 Sb1 Br4 99.774(12) . . ?
Br2 Sb1 Br4 89.442(11) . . ?
Br3 Sb1 Br1 173.767(13) . . ?
Br3 Sb1 Br2 90.299(12) . . ?
Br3 Sb1 Br4 85.332(12) . . ?
Br5 Sb1 Br1 92.801(12) . . ?
Br5 Sb1 Br2 178.407(13) . . ?
Br5 Sb1 Br3 90.581(13) . . ?
Br5 Sb1 Br4 91.953(12) . . ?
Br6 Sb1 Br1 88.425(12) . . ?
Br6 Sb1 Br2 89.393(13) . . ?
Br6 Sb1 Br3 86.380(12) . . ?
Br6 Sb1 Br4 171.623(13) . . ?
Br6 Sb1 Br5 89.338(13) . . ?
N1 C1 C2 114.2(3) . . ?
C3 C2 C1 118.1(4) . . ?
C7 C2 C1 121.3(4) . . ?
C7 C2 C3 120.5(4) . . ?
C2 C3 C4 117.1(4) . . ?
C5 C4 C3 117.7(4) . . ?
C4 C5 C6 122.3(4) . . ?
C5 C6 C7 120.9(4) . . ?
C6 C7 C2 121.6(4) . . ?
N2 C8 C9 114.9(3) . . ?
C10 C9 C8 122.8(3) . . ?
C14 C9 C8 118.2(3) . . ?
C14 C9 C10 118.9(3) . . ?
C9 C10 C11 120.4(3) . . ?
C12 C11 C10 120.4(3) . . ?
C11 C12 C13 119.4(4) . . ?
C12 C13 C14 120.4(4) . . ?
C9 C14 C13 120.5(3) . . ?
N3 C15 C16 111.7(3) . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 C21 118.5(3) . . ?
C21 C16 C15 121.7(3) . . ?
C16 C17 C18 120.2(4) . . ?
C19 C18 C17 120.5(4) . . ?
C18 C19 C20 119.9(4) . . ?
C19 C20 C21 120.3(4) . . ?
C20 C21 C16 120.6(4) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.500 55.7 0.0 ?
2 0.000 0.500 0.000 55.7 0.0 ?

_olex2_submission_special_instructions 'No special instructions were received'
