# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_IG296white
_database_code_depnum_ccdc_archive 'CCDC 1863740'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H9 Bi Br2 Cl4 N2'
_chemical_formula_weight         667.79

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.12752(19)
_cell_length_b                   17.6661(4)
_cell_length_c                   13.3872(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.272(3)
_cell_angle_gamma                90
_cell_volume                     1682.90(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4174
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      28.79

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.636
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    15.847
_shelx_estimated_absorpt_T_min   0.070
_shelx_estimated_absorpt_T_max   0.163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.44241
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            8384
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.259
_diffrn_reflns_theta_max         29.058
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3763
_reflns_number_gt                3252
_reflns_threshold_expression     >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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_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)+(0.0174P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3763
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0595
_refine_ls_wR_factor_gt          0.0564
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.75064(2) 0.43686(2) 0.01105(2) 0.01139(7) Uani 1 1 d . . . . .
Cl1 Cl 0.60826(18) 0.32593(7) -0.08675(10) 0.0181(3) Uani 1 1 d . . . . .
Cl2 Cl 0.89943(19) 0.35418(8) 0.14732(10) 0.0222(3) Uani 1 1 d . . . . .
Cl3 Cl 0.94407(18) 0.57027(7) 0.10169(10) 0.0210(3) Uani 1 1 d . . . . .
Cl4 Cl 0.55299(17) 0.54793(7) -0.12328(9) 0.0164(3) Uani 1 1 d . . . . .
N1 N 0.7346(6) 0.5173(2) 0.4561(3) 0.0166(10) Uani 1 1 d . . . . .
Br1 Br 0.82643(8) 0.58307(3) 0.63939(4) 0.02468(14) Uani 1 1 d . . . . .
C11 C 0.7470(6) 0.5839(3) 0.5020(4) 0.0154(12) Uani 1 1 d . . . . .
C12 C 0.7076(7) 0.6529(3) 0.4557(4) 0.0185(12) Uani 1 1 d . . . . .
H12 H 0.718754 0.699198 0.491758 0.022 Uiso 1 1 calc R U . . .
C13 C 0.6521(7) 0.6517(3) 0.3560(4) 0.0199(12) Uani 1 1 d . . . . .
H13 H 0.624689 0.697720 0.321447 0.024 Uiso 1 1 calc R U . . .
C14 C 0.6363(7) 0.5842(3) 0.3063(4) 0.0201(12) Uani 1 1 d . . . . .
H14 H 0.596711 0.582680 0.237312 0.024 Uiso 1 1 calc R U . . .
C15 C 0.6792(8) 0.5179(3) 0.3582(4) 0.0213(13) Uani 1 1 d . . . . .
H15 H 0.669066 0.471052 0.323434 0.026 Uiso 1 1 calc R U . . .
N2 N 0.7940(5) 0.3746(2) 0.5541(3) 0.0146(10) Uani 1 1 d . . . . .
H2 H 0.780880 0.417472 0.520935 0.018 Uiso 1 1 calc R U . . .
Br2 Br 0.68969(8) 0.31274(3) 0.36978(4) 0.02428(14) Uani 1 1 d . . . . .
C21 C 0.7590(6) 0.3084(3) 0.5058(4) 0.0151(11) Uani 1 1 d . . . . .
C22 C 0.7748(7) 0.2413(3) 0.5558(4) 0.0177(12) Uani 1 1 d . . . . .
H22 H 0.746877 0.194932 0.522316 0.021 Uiso 1 1 calc R U . . .
C23 C 0.8325(7) 0.2421(3) 0.6569(4) 0.0191(12) Uani 1 1 d . . . . .
H23 H 0.846113 0.195905 0.692974 0.023 Uiso 1 1 calc R U . . .
C24 C 0.8700(7) 0.3103(3) 0.7045(4) 0.0186(12) Uani 1 1 d . . . . .
H24 H 0.910384 0.311497 0.773382 0.022 Uiso 1 1 calc R U . . .
C25 C 0.8481(7) 0.3761(3) 0.6512(4) 0.0162(12) Uani 1 1 d . . . . .
H25 H 0.871750 0.423264 0.683518 0.019 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 Cl1 2.5362(12) . yes
Bi1 Cl2 2.5229(13) . yes
Bi1 Cl3 2.7209(13) 3_765 yes
Bi1 Cl3 2.9559(13) . yes
Bi1 Cl4 2.7173(13) 3_665 yes
Bi1 Cl4 2.9630(13) . yes
N1 C11 1.327(7) . ?
N1 C15 1.347(6) . ?
Br1 C11 1.894(5) . ?
C11 C12 1.390(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.371(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.368(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(7) . ?
C15 H15 0.9500 . ?
N2 H2 0.8800 . ?
N2 C21 1.353(6) . ?
N2 C25 1.334(6) . ?
Br2 C21 1.861(5) . ?
C21 C22 1.362(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.392(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.383(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.369(7) . ?
C25 H25 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
Cl1 Bi1 Cl3 89.26(4) . 3_765 yes
Cl1 Bi1 Cl3 172.53(4) . . yes
Cl1 Bi1 Cl4 92.07(4) . . yes
Cl1 Bi1 Cl4 93.09(4) . 3_665 yes
Cl2 Bi1 Cl1 93.74(4) . . yes
Cl2 Bi1 Cl3 89.87(4) . . yes
Cl2 Bi1 Cl3 93.32(4) . 3_765 yes
Cl2 Bi1 Cl4 88.43(4) . 3_665 yes
Cl2 Bi1 Cl4 171.08(4) . . yes
Cl3 Bi1 Cl3 84.01(4) 3_765 . yes
Cl3 Bi1 Cl4 85.16(4) . . yes
Cl3 Bi1 Cl4 93.53(4) 3_765 . yes
Cl4 Bi1 Cl3 93.54(4) 3_665 . yes
Cl4 Bi1 Cl3 176.98(4) 3_665 3_765 yes
Cl4 Bi1 Cl4 84.49(4) 3_665 . yes
Bi1 Cl3 Bi1 95.99(4) 3_765 . yes
Bi1 Cl4 Bi1 95.51(4) 3_665 . yes
C11 N1 C15 116.9(5) . . ?
N1 C11 Br1 116.8(4) . . ?
N1 C11 C12 124.4(5) . . ?
C12 C11 Br1 118.8(4) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 C11 117.4(5) . . ?
C13 C12 H12 121.3 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.9(5) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.6 . . ?
C13 C14 C15 118.9(5) . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 122.5(5) . . ?
N1 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C21 N2 H2 119.4 . . ?
C25 N2 H2 119.4 . . ?
C25 N2 C21 121.1(5) . . ?
N2 C21 Br2 117.6(4) . . ?
N2 C21 C22 120.6(5) . . ?
C22 C21 Br2 121.8(4) . . ?
C21 C22 H22 120.6 . . ?
C21 C22 C23 118.8(5) . . ?
C23 C22 H22 120.6 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.7(5) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 120.5 . . ?
C25 C24 C23 119.1(5) . . ?
C25 C24 H24 120.5 . . ?
N2 C25 C24 120.7(5) . . ?
N2 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?

_refine_diff_density_max         0.927
_refine_diff_density_min         -1.583
_refine_diff_density_rms         0.194

####################################################################### 
# 
# 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_IG366
_database_code_depnum_ccdc_archive 'CCDC 1863747'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 Bi Br2 Cl5 N2'
_chemical_formula_weight         732.30

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

_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'
'-x+1/2, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x, y-1/2, z-1/2'

_cell_length_a                   21.9138(9)
_cell_length_b                   8.3002(3)
_cell_length_c                   11.1021(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2019.35(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2622
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      28.87

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.409
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    13.346
_shelx_estimated_absorpt_T_min   0.123
_shelx_estimated_absorpt_T_max   0.617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38201
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            5990
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.339
_diffrn_reflns_theta_max         28.961
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2237
_reflns_number_gt                1920
_reflns_threshold_expression     >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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_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)+(0.0195P)²+0.0478P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2237
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0522
_refine_ls_wR_factor_gt          0.0495
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.33677(2) 0.250000 0.750000 0.00936(7) Uani 1 2 d S T P . .
Cl1 Cl 0.42160(5) 0.47046(12) 0.77640(8) 0.0174(2) Uani 1 1 d . . . . .
N1 N 0.39545(15) 0.6922(4) 0.5552(3) 0.0154(7) Uani 1 1 d . . . . .
H1 H 0.404864 0.624219 0.613079 0.019 Uiso 1 1 calc R U . . .
Cl3 Cl 0.250000 0.000000 0.71999(12) 0.0198(3) Uani 1 2 d S T P . .
Cl2 Cl 0.33021(4) 0.30912(13) 0.51290(8) 0.0176(2) Uani 1 1 d . . . . .
C11 C 0.4405(2) 0.7624(4) 0.4914(4) 0.0155(9) Uani 1 1 d . . . . .
C12 C 0.4267(2) 0.8643(5) 0.3970(3) 0.0183(9) Uani 1 1 d . . . . .
H12 H 0.458377 0.910869 0.349978 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3660(2) 0.8979(5) 0.3715(3) 0.0177(9) Uani 1 1 d . . . . .
C14 C 0.3211(2) 0.8276(5) 0.4420(4) 0.0184(9) Uani 1 1 d . . . . .
H14 H 0.279422 0.851812 0.427476 0.022 Uiso 1 1 calc R U . . .
C15 C 0.33661(19) 0.7237(5) 0.5322(4) 0.0190(10) Uani 1 1 d . . . . .
H15 H 0.305607 0.673559 0.578790 0.023 Uiso 1 1 calc R U . . .
C16 C 0.3503(2) 1.0123(6) 0.2716(3) 0.0245(11) Uani 1 1 d . . . . .
H16A H 0.313080 0.975488 0.231089 0.037 Uiso 1 1 calc R U . . .
H16B H 0.383921 1.015980 0.213478 0.037 Uiso 1 1 calc R U . . .
H16C H 0.343570 1.120183 0.304942 0.037 Uiso 1 1 calc R U . . .
Br1 Br 0.52102(2) 0.71723(5) 0.53389(4) 0.02332(11) 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 Cl1 2.6249(10) . yes
Bi1 Cl1 2.6249(10) 4_556 ?
Bi1 Cl2 2.6815(9) . yes
Bi1 Cl2 2.6815(9) 4_556 ?
Bi1 Cl3 2.8341(2) . yes
Bi1 Cl3 2.8341(2) 3_556 ?
N1 H1 0.8800 . ?
N1 C11 1.347(5) . ?
N1 C15 1.340(5) . ?
C11 C12 1.380(5) . ?
C11 Br1 1.865(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(6) . ?
C13 C14 1.386(6) . ?
C13 C16 1.501(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.364(6) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Bi1 Cl1 89.82(5) 4_556 . yes
Cl1 Bi1 Cl3 87.23(2) . 3_556 yes
Cl1 Bi1 Cl3 87.23(2) 4_556 . ?
Cl1 Bi1 Cl3 177.05(2) . . yes
Cl1 Bi1 Cl3 177.05(2) 4_556 3_556 ?
Cl1 Bi1 Cl2 91.14(3) 4_556 4_556 ?
Cl1 Bi1 Cl2 91.15(3) . . yes
Cl1 Bi1 Cl2 93.21(3) . 4_556 yes
Cl1 Bi1 Cl2 93.21(3) 4_556 . ?
Cl3 Bi1 Cl3 95.725(9) . 3_556 yes
Cl2 Bi1 Cl3 86.87(3) . 3_556 yes
Cl2 Bi1 Cl3 86.87(3) 4_556 . ?
Cl2 Bi1 Cl3 89.00(3) . . yes
Cl2 Bi1 Cl3 89.01(3) 4_556 3_556 ?
Cl2 Bi1 Cl2 173.86(4) . 4_556 yes
Bi1 Cl3 Bi1 166.50(5) 2 . yes
C11 N1 H1 119.3 . . ?
C15 N1 H1 119.3 . . ?
C15 N1 C11 121.4(3) . . ?
N1 C11 C12 120.3(4) . . ?
N1 C11 Br1 118.2(3) . . ?
C12 C11 Br1 121.5(3) . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.1(4) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C16 119.9(4) . . ?
C14 C13 C12 118.7(4) . . ?
C14 C13 C16 121.4(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.9 . . ?
N1 C15 C14 120.1(4) . . ?
N1 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.705
_refine_diff_density_min         -1.481
_refine_diff_density_rms         0.162

####################################################################### 
# 
# 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_IG325
_database_code_depnum_ccdc_archive 'CCDC 1863746'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 Bi Br7 N2'
_chemical_formula_weight         926.55

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.1733(3)
_cell_length_b                   10.5445(3)
_cell_length_c                   10.7330(4)
_cell_angle_alpha                100.260(3)
_cell_angle_beta                 97.127(3)
_cell_angle_gamma                108.312(3)
_cell_volume                     951.67(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3404
_cell_measurement_theta_min      3.97
_cell_measurement_theta_max      28.66

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.233
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    23.950
_shelx_estimated_absorpt_T_min   0.114
_shelx_estimated_absorpt_T_max   0.328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.25029
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            7197
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.370
_diffrn_reflns_theta_max         29.136
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.813
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.813
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4174
_reflns_number_gt                3614
_reflns_threshold_expression     >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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_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)+(0.0150P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4174
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0560
_refine_ls_wR_factor_gt          0.0525
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 0.42145(2) 0.63128(2) 0.64353(2) 0.01162(7) Uani 1 1 d . . . . .
Br11 Br 0.56762(6) 0.86079(5) 0.84531(6) 0.01877(14) Uani 1 1 d . . . . .
Br12 Br 0.45798(6) 0.80393(5) 0.46393(6) 0.01588(14) Uani 1 1 d . . . . .
Br13 Br 0.12852(6) 0.62911(6) 0.66296(7) 0.01782(15) Uani 1 1 d . . . . .
Br14 Br 0.40234(6) 0.46039(5) 0.82133(6) 0.01643(14) Uani 1 1 d . . . . .
Br15 Br 0.72247(6) 0.60254(5) 0.59270(6) 0.01494(14) Uani 1 1 d . . . . .
N1 N 0.1386(5) 0.8703(5) 0.4142(5) 0.0194(12) Uani 1 1 d . . . . .
H1 H 0.217400 0.850075 0.450270 0.023 Uiso 1 1 calc R U . . .
C11 C -0.0066(6) 0.8065(5) 0.4338(6) 0.0171(14) Uani 1 1 d . . . . .
H11 H -0.022682 0.740255 0.484852 0.021 Uiso 1 1 calc R U . . .
C12 C -0.1305(6) 0.8377(5) 0.3799(6) 0.0128(13) Uani 1 1 d . . . . .
H12 H -0.232692 0.794543 0.394167 0.015 Uiso 1 1 calc R U . . .
C13 C -0.1044(6) 0.9332(5) 0.3040(6) 0.0153(13) Uani 1 1 d . . . . .
C14 C 0.0458(6) 0.9967(6) 0.2854(7) 0.0206(15) Uani 1 1 d . . . . .
H14 H 0.064484 1.062589 0.233948 0.025 Uiso 1 1 calc R U . . .
C15 C 0.1664(7) 0.9635(6) 0.3415(7) 0.0214(15) Uani 1 1 d . . . . .
H15 H 0.269745 1.006288 0.329282 0.026 Uiso 1 1 calc R U . . .
Br1 Br -0.27193(7) 0.97765(6) 0.23014(7) 0.02333(16) Uani 1 1 d . . . . .
N2 N 0.7151(5) 0.3722(4) 0.8549(5) 0.0176(12) Uani 1 1 d . . . . .
H2 H 0.640758 0.400220 0.823089 0.021 Uiso 1 1 calc R U . . .
C21 C 0.6856(6) 0.2934(6) 0.9395(7) 0.0216(15) Uani 1 1 d . . . . .
H21 H 0.586409 0.269095 0.964233 0.026 Uiso 1 1 calc R U . . .
C22 C 0.7984(6) 0.2475(5) 0.9908(6) 0.0191(14) Uani 1 1 d . . . . .
H22 H 0.778295 0.189215 1.049364 0.023 Uiso 1 1 calc R U . . .
C23 C 0.9425(6) 0.2885(5) 0.9546(6) 0.0158(13) Uani 1 1 d . . . . .
C24 C 0.9707(6) 0.3699(5) 0.8654(6) 0.0145(13) Uani 1 1 d . . . . .
H24 H 1.069216 0.396431 0.839622 0.017 Uiso 1 1 calc R U . . .
C25 C 0.8528(6) 0.4109(5) 0.8158(6) 0.0174(14) Uani 1 1 d . . . . .
H25 H 0.868103 0.466069 0.754281 0.021 Uiso 1 1 calc R U . . .
Br2 Br 1.10679(7) 0.23631(6) 1.02833(7) 0.02299(15) 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 Br11 2.7782(7) . yes
Bi1 Br12 2.8583(6) . yes
Bi1 Br13 2.7142(5) . yes
Bi1 Br14 2.8336(6) . yes
Bi1 Br15 2.9757(5) . yes
Bi1 Br15 3.0245(7) 2_666 yes
N1 H1 0.8800 . ?
N1 C11 1.352(7) . ?
N1 C15 1.344(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.368(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(7) . ?
C13 C14 1.387(7) . ?
C13 Br1 1.869(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.365(8) . ?
C15 H15 0.9500 . ?
N2 H2 0.8800 . ?
N2 C21 1.332(7) . ?
N2 C25 1.344(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.370(8) . ?
C22 H22 0.9500 . ?
C22 C23 1.382(7) . ?
C23 C24 1.392(8) . ?
C23 Br2 1.892(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.368(7) . ?
C25 H25 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
Br11 Bi1 Br12 89.871(18) . . yes
Br11 Bi1 Br14 89.769(19) . . yes
Br11 Bi1 Br15 93.351(17) . . yes
Br11 Bi1 Br15 174.583(17) . 2_666 yes
Br12 Bi1 Br15 85.112(18) . 2_666 yes
Br12 Bi1 Br15 85.728(16) . . yes
Br13 Bi1 Br11 94.165(19) . . yes
Br13 Bi1 Br12 93.930(17) . . yes
Br13 Bi1 Br14 89.231(17) . . yes
Br13 Bi1 Br15 88.226(18) . 2_666 yes
Br13 Bi1 Br15 172.48(2) . . yes
Br14 Bi1 Br12 176.837(16) . . yes
Br14 Bi1 Br15 91.156(16) . . yes
Br14 Bi1 Br15 95.129(17) . 2_666 yes
Br15 Bi1 Br15 84.255(17) . 2_666 yes
Bi1 Br15 Bi1 95.746(17) . 2_666 yes
C11 N1 H1 119.0 . . ?
C15 N1 H1 119.0 . . ?
C15 N1 C11 122.1(5) . . ?
N1 C11 H11 120.1 . . ?
N1 C11 C12 119.9(5) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.0(5) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C14 119.9(5) . . ?
C12 C13 Br1 119.6(4) . . ?
C14 C13 Br1 120.5(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.4(5) . . ?
C15 C14 H14 120.3 . . ?
N1 C15 C14 119.8(5) . . ?
N1 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C21 N2 H2 118.4 . . ?
C21 N2 C25 123.2(5) . . ?
C25 N2 H2 118.4 . . ?
N2 C21 H21 120.0 . . ?
N2 C21 C22 120.0(5) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 121.0 . . ?
C21 C22 C23 118.0(5) . . ?
C23 C22 H22 121.0 . . ?
C22 C23 C24 121.1(5) . . ?
C22 C23 Br2 120.2(4) . . ?
C24 C23 Br2 118.7(4) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 C23 118.3(5) . . ?
C25 C24 H24 120.9 . . ?
N2 C25 C24 119.3(5) . . ?
N2 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?

_refine_diff_density_max         1.659
_refine_diff_density_min         -1.605
_refine_diff_density_rms         0.220

####################################################################### 
# 
# 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_IG337new
_database_code_depnum_ccdc_archive 'CCDC 1863744'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-10-26 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            'C10 H12 Bi Br7 N2 O'
_chemical_formula_weight         944.57

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

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

_cell_length_a                   8.2817(4)
_cell_length_b                   20.8514(11)
_cell_length_c                   12.0986(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2089.25(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2773
_cell_measurement_theta_min      3.80
_cell_measurement_theta_max      28.57

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.003
_exptl_crystal_F_000             1688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    21.825
_shelx_estimated_absorpt_T_min   0.025
_shelx_estimated_absorpt_T_max   0.354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.16062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            8918
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.368
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.721
_diffrn_reflns_point_group_measured_fraction_full 0.726
_reflns_number_total             2852
_reflns_number_gt                2667
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.376
_reflns_Friedel_fraction_max     0.415
_reflns_Friedel_fraction_full    0.428

_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2018 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB (Sheldrick, 2015)'

_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)+(0.0615P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.020(16)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2852
_refine_ls_number_parameters     190
_refine_ls_number_restraints     25
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.032
_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 0.70068(6) 0.64499(2) 0.50253(6) 0.00899(16) Uani 1 1 d . . . . .
Br11 Br 0.72417(19) 0.61920(8) 0.72783(14) 0.0175(4) Uani 1 1 d . . . . .
Br12 Br 0.50337(19) 0.53840(7) 0.48270(15) 0.0209(4) Uani 1 1 d . . . . .
Br13 Br 0.96128(19) 0.57362(8) 0.45728(14) 0.0205(4) Uani 1 1 d . . . . .
Br14 Br 0.67423(19) 0.66909(8) 0.26494(13) 0.0159(4) Uani 1 1 d . . . . .
Br15 Br 0.90335(18) 0.76248(7) 0.51313(17) 0.0222(4) Uani 1 1 d . . . . .
N1 N 0.2357(18) 0.6012(7) 0.7521(14) 0.022(3) Uani 1 1 d . U . . .
H1 H 0.229527 0.563761 0.718927 0.026 Uiso 1 1 calc R U . . .
C11 C 0.328(2) 0.6076(9) 0.8433(15) 0.022(4) Uani 1 1 d . U . . .
H11 H 0.383994 0.571409 0.871714 0.026 Uiso 1 1 calc R U . . .
C12 C 0.3427(19) 0.6648(8) 0.8945(15) 0.016(4) Uani 1 1 d . . . . .
C13 C 0.2623(18) 0.7164(8) 0.8519(15) 0.020(4) Uani 1 1 d . . . . .
H13 H 0.272636 0.757256 0.885940 0.024 Uiso 1 1 calc R U . . .
C14 C 0.1660(19) 0.7094(9) 0.7595(15) 0.022(4) Uani 1 1 d . . . . .
H14 H 0.109426 0.745108 0.729724 0.026 Uiso 1 1 calc R U . . .
C15 C 0.154(2) 0.6508(8) 0.7120(16) 0.021(4) Uani 1 1 d . U . . .
H15 H 0.085779 0.645069 0.649442 0.025 Uiso 1 1 calc R U . . .
Br1 Br 0.47754(19) 0.67015(8) 1.01995(15) 0.0209(4) Uani 1 1 d . . . . .
N2 N 1.1706(15) 0.6727(7) 0.2570(13) 0.017(3) Uani 1 1 d . U . . .
H2 H 1.177789 0.708769 0.294443 0.021 Uiso 1 1 calc R U . . .
C21 C 1.0743(19) 0.6713(8) 0.1696(15) 0.018(3) Uani 1 1 d . U . . .
H21 H 1.012736 0.707894 0.149132 0.022 Uiso 1 1 calc R U . . .
C22 C 1.0660(18) 0.6156(8) 0.1095(14) 0.014(4) Uani 1 1 d . . . . .
C23 C 1.153(2) 0.5628(8) 0.1420(14) 0.016(4) Uani 1 1 d . . . . .
H23 H 1.146178 0.524021 0.100910 0.019 Uiso 1 1 calc R U . . .
C24 C 1.248(2) 0.5661(8) 0.2333(15) 0.017(4) Uani 1 1 d . . . . .
H24 H 1.308396 0.529724 0.256590 0.021 Uiso 1 1 calc R U . . .
C25 C 1.257(2) 0.6228(8) 0.2917(15) 0.017(3) Uani 1 1 d . U . . .
H25 H 1.323595 0.626105 0.355484 0.021 Uiso 1 1 calc R U . . .
Br2 Br 0.93205(19) 0.61494(8) -0.01851(14) 0.0214(4) Uani 1 1 d . . . . .
O1W O 0.2471(17) 0.4814(6) 0.6776(13) 0.041(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Br11 2.7852(18) . yes
Bi1 Br12 2.7690(15) . yes
Bi1 Br13 2.6782(16) . yes
Bi1 Br14 2.9262(18) . yes
Bi1 Br15 2.9724(15) . yes
Bi1 Br15 3.1308(15) 3_465 yes
N1 H1 0.8800 . ?
N1 C11 1.35(2) . ?
N1 C15 1.33(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.35(2) . ?
C12 C13 1.37(2) . ?
C12 Br1 1.887(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.38(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.35(2) . ?
C15 H15 0.9500 . ?
N2 H2 0.8800 . ?
N2 C21 1.32(2) . ?
N2 C25 1.33(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.37(2) . ?
C22 C23 1.37(2) . ?
C22 Br2 1.906(17) . ?
C23 H23 0.9500 . ?
C23 C24 1.36(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.38(2) . ?
C25 H25 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
Br11 Bi1 Br14 178.72(5) . . yes
Br11 Bi1 Br15 94.44(5) . . yes
Br11 Bi1 Br15 97.69(5) . 3_465 yes
Br12 Bi1 Br11 88.34(5) . . yes
Br12 Bi1 Br14 90.49(5) . . yes
Br12 Bi1 Br15 91.95(5) . 3_465 yes
Br12 Bi1 Br15 176.86(6) . . yes
Br13 Bi1 Br11 92.09(5) . . yes
Br13 Bi1 Br12 90.68(5) . . yes
Br13 Bi1 Br14 87.42(5) . . yes
Br13 Bi1 Br15 90.67(5) . . yes
Br13 Bi1 Br15 169.94(6) . 3_465 yes
Br14 Bi1 Br15 82.85(5) . 3_465 yes
Br14 Bi1 Br15 86.74(5) . . yes
Br15 Bi1 Br15 86.243(16) . 3_465 yes
Bi1 Br15 Bi1 161.85(6) . 3_565 yes
C11 N1 H1 119.6 . . ?
C15 N1 H1 119.6 . . ?
C15 N1 C11 120.8(16) . . ?
N1 C11 H11 119.6 . . ?
N1 C11 C12 120.9(17) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 118.6(17) . . ?
C11 C12 Br1 118.3(14) . . ?
C13 C12 Br1 123.1(13) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.3(17) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.8(17) . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 120.5(17) . . ?
N1 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C21 N2 H2 118.0 . . ?
C21 N2 C25 124.0(15) . . ?
C25 N2 H2 118.0 . . ?
N2 C21 H21 120.9 . . ?
N2 C21 C22 118.1(15) . . ?
C22 C21 H21 120.9 . . ?
C21 C22 C23 120.1(16) . . ?
C21 C22 Br2 117.8(12) . . ?
C23 C22 Br2 122.1(13) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.7(16) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.4(17) . . ?
C25 C24 H24 120.3 . . ?
N2 C25 C24 118.7(17) . . ?
N2 C25 H25 120.7 . . ?
C24 C25 H25 120.7 . . ?

_refine_diff_density_max         1.972
_refine_diff_density_min         -2.868
_refine_diff_density_rms         0.271

####################################################################### 
# 
# 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_IG296yellow
_database_code_depnum_ccdc_archive 'CCDC 1863741'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 Bi Br2 Cl5 N2'
_chemical_formula_weight         704.25

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   5.5707(3)
_cell_length_b                   15.7750(8)
_cell_length_c                   10.5170(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.307(5)
_cell_angle_gamma                90
_cell_volume                     895.55(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    1594
_cell_measurement_theta_min      3.98
_cell_measurement_theta_max      28.77

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.612
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    15.041
_shelx_estimated_absorpt_T_min   0.162
_shelx_estimated_absorpt_T_max   0.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.47932
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            3882
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.775
_diffrn_reflns_theta_max         28.980
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1962
_reflns_number_gt                1651
_reflns_threshold_expression     >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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_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)+(0.0384P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1962
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.500000 0.500000 0.500000 0.01382(12) Uani 1 2 d S . P . .
Cl1 Cl 0.4635(3) 0.33740(10) 0.42150(14) 0.0210(3) Uani 1 1 d . . . . .
Cl2 Cl 0.6022(3) 0.44679(11) 0.74836(16) 0.0272(4) Uani 1 1 d . . . . .
Cl3 Cl 1.000000 0.500000 0.500000 0.0440(8) Uani 1 2 d S . P . .
N1 N 0.1325(10) 0.2569(3) 0.0796(5) 0.0208(12) Uani 1 1 d . . . . .
H1 H 0.225099 0.227313 0.039094 0.025 Uiso 1 1 calc R U . . .
Br1 Br 0.30668(12) 0.38855(4) -0.04373(6) 0.02250(17) Uani 1 1 d . . . . .
C11 C 0.1235(11) 0.3408(4) 0.0663(6) 0.0174(13) Uani 1 1 d . . . . .
C12 C -0.0154(12) 0.3890(5) 0.1280(6) 0.0251(15) Uani 1 1 d . . . . .
H12 H -0.020199 0.448921 0.118299 0.030 Uiso 1 1 calc R U . . .
C13 C -0.1497(12) 0.3493(5) 0.2053(6) 0.0249(15) Uani 1 1 d . . . . .
H13 H -0.248589 0.381767 0.249057 0.030 Uiso 1 1 calc R U . . .
C14 C -0.1394(11) 0.2617(4) 0.2186(6) 0.0223(15) Uani 1 1 d . . . . .
H14 H -0.229560 0.233576 0.271927 0.027 Uiso 1 1 calc R U . . .
C15 C 0.0034(12) 0.2165(5) 0.1535(6) 0.0255(15) Uani 1 1 d . . . . .
H15 H 0.011011 0.156433 0.160578 0.031 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 Cl1 2.6869(16) . yes
Bi1 Cl1 2.6869(16) 3_666 ?
Bi1 Cl2 2.6676(16) 3_666 ?
Bi1 Cl2 2.6677(16) . yes
Bi1 Cl3 2.78535(15) . yes
Bi1 Cl3 2.78535(15) 1_455 ?
N1 H1 0.8800 . ?
N1 C11 1.331(8) . ?
N1 C15 1.344(8) . ?
Br1 C11 1.879(6) . ?
C11 C12 1.359(9) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.371(9) . ?
C15 H15 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
Cl1 Bi1 Cl1 180.0 . 3_666 yes
Cl1 Bi1 Cl3 89.99(3) . . yes
Cl1 Bi1 Cl3 89.99(3) 3_666 1_455 ?
Cl1 Bi1 Cl3 90.01(3) . 1_455 yes
Cl1 Bi1 Cl3 90.01(3) 3_666 . ?
Cl2 Bi1 Cl1 88.97(5) . . yes
Cl2 Bi1 Cl1 88.97(5) 3_666 3_666 ?
Cl2 Bi1 Cl1 91.03(5) . 3_666 yes
Cl2 Bi1 Cl1 91.03(5) 3_666 . ?
Cl2 Bi1 Cl2 180.00(8) 3_666 . yes
Cl2 Bi1 Cl3 88.36(4) . 1_455 yes
Cl2 Bi1 Cl3 88.36(4) 3_666 . ?
Cl2 Bi1 Cl3 91.64(4) . . yes
Cl2 Bi1 Cl3 91.64(4) 3_666 1_455 ?
Cl3 Bi1 Cl3 180.0 1_455 . yes
Bi1 Cl3 Bi1 180.0 1_655 . yes
C11 N1 H1 119.3 . . ?
C11 N1 C15 121.4(6) . . ?
C15 N1 H1 119.3 . . ?
N1 C11 Br1 116.8(5) . . ?
N1 C11 C12 121.2(6) . . ?
C12 C11 Br1 122.0(5) . . ?
C11 C12 H12 120.6 . . ?
C11 C12 C13 118.8(7) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.7(6) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.8(6) . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 120.1(6) . . ?
N1 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?

_refine_diff_density_max         1.870
_refine_diff_density_min         -2.241
_refine_diff_density_rms         0.235

####################################################################### 
# 
# 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_IG337
_database_code_depnum_ccdc_archive 'CCDC 1863743'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H21 Bi2 Br12 N3 O3'
_chemical_formula_weight         1668.23

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.3220(3)
_cell_length_b                   20.3199(7)
_cell_length_c                   9.6981(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.515(3)
_cell_angle_gamma                90
_cell_volume                     1806.19(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3339
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      28.21

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.067
_exptl_crystal_F_000             1484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    23.026
_shelx_estimated_absorpt_T_min   0.034
_shelx_estimated_absorpt_T_max   0.339
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-13 -1 5 0.1636
8 6 9 0.1015
-9 -6 -7 0.1230
8 -3 -12 0.1761
-1 28 -1 0.0428
1 -28 1 0.0209

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            7353
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.352
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.792
_diffrn_reflns_point_group_measured_fraction_full 0.794
_reflns_number_total             5242
_reflns_number_gt                4817
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.541
_reflns_Friedel_fraction_max     0.573
_reflns_Friedel_fraction_full    0.577

_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_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)+(0.0254P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1534 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.037(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5242
_refine_ls_number_parameters     316
_refine_ls_number_restraints     103
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.993
_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 0.79970(8) 0.48705(4) 0.45445(8) 0.01127(19) Uani 1 1 d . . . . .
Bi2 Bi 0.69251(8) 0.67310(4) 0.40962(8) 0.0127(2) Uani 1 1 d . . . . .
Br11 Br 0.9673(2) 0.43230(11) 0.6958(2) 0.0166(5) Uani 1 1 d . . . . .
Br12 Br 0.9451(2) 0.42128(12) 0.2773(2) 0.0173(5) Uani 1 1 d . . . . .
Br13 Br 0.5962(2) 0.39104(11) 0.4459(2) 0.0166(5) Uani 1 1 d . . . . .
Br14 Br 0.6305(2) 0.55776(11) 0.2111(2) 0.0153(5) Uani 1 1 d . . . . .
Br15 Br 0.6263(2) 0.57258(11) 0.6228(2) 0.0172(5) Uani 1 1 d . . . . .
Br16 Br 0.9907(2) 0.60887(11) 0.4720(2) 0.0154(5) Uani 1 1 d . . . . .
Br17 Br 0.7691(2) 0.76123(13) 0.6244(2) 0.0253(6) Uani 1 1 d . . . . .
Br18 Br 0.7767(2) 0.74488(12) 0.1991(2) 0.0226(5) Uani 1 1 d . . . . .
Br19 Br 0.4113(2) 0.71197(13) 0.3470(2) 0.0262(6) Uani 1 1 d . . . . .
N1 N 0.7319(19) 0.2468(9) 0.3239(19) 0.020(3) Uani 1 1 d . U . . .
H1 H 0.766063 0.247268 0.414678 0.024 Uiso 1 1 calc R U . . .
C11 C 0.825(2) 0.2543(11) 0.235(2) 0.020(3) Uani 1 1 d . U . . .
H11 H 0.925416 0.262016 0.270220 0.024 Uiso 1 1 calc R U . . .
C12 C 0.774(2) 0.2507(11) 0.094(2) 0.019(3) Uani 1 1 d . U . . .
C13 C 0.627(2) 0.2419(11) 0.041(2) 0.021(3) Uani 1 1 d . U . . .
H13 H 0.591496 0.238664 -0.056790 0.025 Uiso 1 1 calc R U . . .
C14 C 0.532(2) 0.2378(12) 0.136(2) 0.022(3) Uani 1 1 d . U . . .
H14 H 0.429989 0.234512 0.103949 0.026 Uiso 1 1 calc R U . . .
C15 C 0.589(2) 0.2387(11) 0.279(2) 0.022(3) Uani 1 1 d . U . . .
H15 H 0.526252 0.233547 0.345367 0.026 Uiso 1 1 calc R U . . .
Br1 Br 0.9068(3) 0.26125(14) -0.0301(3) 0.0347(7) Uani 1 1 d . . . . .
N2 N 0.4633(19) 0.4036(9) 0.7664(18) 0.018(3) Uani 1 1 d . U . . .
H2 H 0.433164 0.402474 0.674961 0.022 Uiso 1 1 calc R U . . .
C21 C 0.363(2) 0.4000(11) 0.851(2) 0.020(3) Uani 1 1 d . U . . .
H21 H 0.261877 0.398433 0.810924 0.024 Uiso 1 1 calc R U . . .
C22 C 0.406(2) 0.3985(12) 0.992(2) 0.022(3) Uani 1 1 d . U . . .
C23 C 0.553(2) 0.4060(11) 1.050(2) 0.021(3) Uani 1 1 d . U . . .
H23 H 0.584095 0.408189 1.149084 0.025 Uiso 1 1 calc R U . . .
C24 C 0.651(3) 0.4101(11) 0.961(2) 0.022(3) Uani 1 1 d . U . . .
H24 H 0.751911 0.413893 0.999681 0.027 Uiso 1 1 calc R U . . .
C25 C 0.607(2) 0.4087(11) 0.816(2) 0.019(3) Uani 1 1 d . U . . .
H25 H 0.675435 0.411384 0.754819 0.023 Uiso 1 1 calc R U . . .
Br2 Br 0.2616(3) 0.39253(14) 1.1028(3) 0.0333(6) Uani 1 1 d . U . . .
N3 N 0.1300(18) 0.5729(9) 0.1474(18) 0.019(4) Uani 1 1 d . U . . .
H3 H 0.159293 0.566366 0.237809 0.023 Uiso 1 1 calc R U . . .
C31 C 0.230(3) 0.5695(12) 0.060(2) 0.024(4) Uani 1 1 d . U . . .
H31 H 0.330862 0.562571 0.095203 0.029 Uiso 1 1 calc R U . . .
C32 C 0.179(3) 0.5763(12) -0.080(2) 0.023(3) Uani 1 1 d . U . . .
C33 C 0.032(3) 0.5887(12) -0.132(2) 0.023(4) Uani 1 1 d . U . . .
H33 H -0.002045 0.594611 -0.229299 0.028 Uiso 1 1 calc R U . . .
C34 C -0.062(2) 0.5923(11) -0.042(2) 0.020(5) Uani 1 1 d . . . . .
H34 H -0.163321 0.599094 -0.075180 0.024 Uiso 1 1 calc R U . . .
C35 C -0.009(2) 0.5859(12) 0.099(2) 0.022(5) Uani 1 1 d . U . . .
H35 H -0.074200 0.590918 0.163851 0.026 Uiso 1 1 calc R U . . .
Br3 Br 0.3163(3) 0.57076(12) -0.2021(3) 0.0272(6) Uani 1 1 d . U . . .
O1 O 0.8990(15) 0.2754(8) 0.5727(16) 0.023(4) Uani 1 1 d . . . . .
O2 O 0.2599(15) 0.4115(8) 0.5194(15) 0.026(4) Uani 1 1 d . . . . .
O3 O 0.3054(15) 0.5345(7) 0.3831(15) 0.021(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Br11 2.796(2) . ?
Bi1 Br12 2.725(2) . ?
Bi1 Br13 2.712(2) . ?
Bi1 Br14 2.960(2) . ?
Bi1 Br15 3.044(2) . ?
Bi1 Br16 3.036(2) . ?
Bi2 Br14 3.021(2) . ?
Bi2 Br15 3.049(2) . ?
Bi2 Br16 3.031(2) . ?
Bi2 Br17 2.741(2) . ?
Bi2 Br18 2.738(2) . ?
Bi2 Br19 2.699(2) . ?
N1 H1 0.8800 . ?
N1 C11 1.33(3) . ?
N1 C15 1.33(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.37(3) . ?
C12 C13 1.38(3) . ?
C12 Br1 1.89(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.39(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.39(3) . ?
C15 H15 0.9500 . ?
N2 H2 0.8800 . ?
N2 C21 1.35(3) . ?
N2 C25 1.34(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.35(3) . ?
C22 C23 1.39(3) . ?
C22 Br2 1.87(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.37(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.39(3) . ?
C25 H25 0.9500 . ?
N3 H3 0.8800 . ?
N3 C31 1.38(3) . ?
N3 C35 1.32(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.36(3) . ?
C32 C33 1.40(3) . ?
C32 Br3 1.90(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.35(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.37(3) . ?
C35 H35 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
Br11 Bi1 Br14 174.41(7) . . ?
Br11 Bi1 Br15 92.78(6) . . ?
Br11 Bi1 Br16 92.59(6) . . ?
Br12 Bi1 Br11 93.81(7) . . ?
Br12 Bi1 Br14 89.38(6) . . ?
Br12 Bi1 Br15 172.91(7) . . ?
Br12 Bi1 Br16 94.66(7) . . ?
Br13 Bi1 Br11 91.15(7) . . ?
Br13 Bi1 Br12 93.05(7) . . ?
Br13 Bi1 Br14 93.26(6) . . ?
Br13 Bi1 Br15 89.44(7) . . ?
Br13 Bi1 Br16 171.19(7) . . ?
Br14 Bi1 Br15 83.85(6) . . ?
Br14 Bi1 Br16 82.57(6) . . ?
Br16 Bi1 Br15 82.41(6) . . ?
Br14 Bi2 Br15 82.74(6) . . ?
Br14 Bi2 Br16 81.66(6) . . ?
Br16 Bi2 Br15 82.42(6) . . ?
Br17 Bi2 Br14 169.78(8) . . ?
Br17 Bi2 Br15 88.81(7) . . ?
Br17 Bi2 Br16 91.57(7) . . ?
Br18 Bi2 Br14 89.17(7) . . ?
Br18 Bi2 Br15 169.66(7) . . ?
Br18 Bi2 Br16 90.06(7) . . ?
Br18 Bi2 Br17 98.53(8) . . ?
Br19 Bi2 Br14 91.07(7) . . ?
Br19 Bi2 Br15 92.28(7) . . ?
Br19 Bi2 Br16 171.47(8) . . ?
Br19 Bi2 Br17 95.01(8) . . ?
Br19 Bi2 Br18 94.31(7) . . ?
Bi1 Br14 Bi2 81.73(5) . . ?
Bi1 Br15 Bi2 79.95(5) . . ?
Bi2 Br16 Bi1 80.37(5) . . ?
C11 N1 H1 118.9 . . ?
C15 N1 H1 118.9 . . ?
C15 N1 C11 122(2) . . ?
N1 C11 H11 120.3 . . ?
N1 C11 C12 119(2) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 121(2) . . ?
C11 C12 Br1 118.8(16) . . ?
C13 C12 Br1 120.1(16) . . ?
C12 C13 H13 121.0 . . ?
C12 C13 C14 118(2) . . ?
C14 C13 H13 121.0 . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119(2) . . ?
C15 C14 H14 120.4 . . ?
N1 C15 C14 120(2) . . ?
N1 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C21 N2 H2 118.6 . . ?
C25 N2 H2 118.6 . . ?
C25 N2 C21 122.9(19) . . ?
N2 C21 H21 120.0 . . ?
N2 C21 C22 120(2) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 120(2) . . ?
C21 C22 Br2 118.0(17) . . ?
C23 C22 Br2 121.9(17) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 C22 118(2) . . ?
C24 C23 H23 121.0 . . ?
C23 C24 H24 119.1 . . ?
C23 C24 C25 122(2) . . ?
C25 C24 H24 119.1 . . ?
N2 C25 C24 117(2) . . ?
N2 C25 H25 121.5 . . ?
C24 C25 H25 121.5 . . ?
C31 N3 H3 119.1 . . ?
C35 N3 H3 119.1 . . ?
C35 N3 C31 122(2) . . ?
N3 C31 H31 121.3 . . ?
C32 C31 N3 117(2) . . ?
C32 C31 H31 121.3 . . ?
C31 C32 C33 121(2) . . ?
C31 C32 Br3 117.7(18) . . ?
C33 C32 Br3 121.2(18) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 C32 119(2) . . ?
C34 C33 H33 120.3 . . ?
C33 C34 H34 120.5 . . ?
C33 C34 C35 119(2) . . ?
C35 C34 H34 120.5 . . ?
N3 C35 C34 121(2) . . ?
N3 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?

_refine_diff_density_max         2.658
_refine_diff_density_min         -3.256
_refine_diff_density_rms         0.316

####################################################################### 
# 
# 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_IG355-1
_database_code_depnum_ccdc_archive 'CCDC 1863748'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H25 Bi2 Br12 N3 O2'
_chemical_formula_weight         1692.29

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.1878(7)
_cell_length_b                   12.1235(9)
_cell_length_c                   19.5314(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.969(8)
_cell_angle_gamma                90
_cell_volume                     1909.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3122
_cell_measurement_theta_min      3.97
_cell_measurement_theta_max      28.64

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.943
_exptl_crystal_F_000             1512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    21.780
_shelx_estimated_absorpt_T_min   0.036
_shelx_estimated_absorpt_T_max   0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36481
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            9858
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.361
_diffrn_reflns_theta_max         29.041
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6912
_reflns_number_gt                6447
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_max     0.843
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.307(13)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6912
_refine_ls_number_parameters     338
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1050
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.073
_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 0.65872(8) 0.73541(5) 0.31831(4) 0.01422(16) Uani 1 1 d . . . . .
Bi2 Bi 0.66023(8) 0.52374(5) 0.16208(4) 0.01397(16) Uani 1 1 d . . . . .
Br11 Br 0.7381(3) 0.67078(17) 0.45421(11) 0.0245(5) Uani 1 1 d . . . . .
Br12 Br 0.8857(2) 0.91604(17) 0.34458(11) 0.0215(4) Uani 1 1 d . . . . .
Br13 Br 0.3937(2) 0.85864(16) 0.34253(11) 0.0196(4) Uani 1 1 d . . . . .
Br14 Br 0.6232(2) 0.77164(15) 0.16232(10) 0.0183(4) Uani 1 1 d . . . . .
Br15 Br 0.4379(2) 0.55166(15) 0.27321(10) 0.0201(4) Uani 1 1 d . . . . .
Br16 Br 0.9158(2) 0.57585(17) 0.28867(11) 0.0222(4) Uani 1 1 d . . . . .
Br17 Br 0.6883(2) 0.30124(15) 0.17902(11) 0.0223(5) Uani 1 1 d . . . . .
Br18 Br 0.8954(3) 0.53739(17) 0.08164(12) 0.0278(5) Uani 1 1 d . . . . .
Br19 Br 0.4107(3) 0.50507(18) 0.04993(13) 0.0368(6) Uani 1 1 d . . . . .
N1 N 0.0370(18) 0.8682(12) 0.1950(9) 0.017(3) Uani 1 1 d . U . . .
H1 H 0.011189 0.888683 0.234984 0.021 Uiso 1 1 calc R U . . .
C11 C -0.015(2) 0.9257(15) 0.1400(11) 0.018(3) Uani 1 1 d . U . . .
C12 C 0.013(2) 0.8961(15) 0.0725(12) 0.022(3) Uani 1 1 d . U . . .
H12 H -0.034265 0.935330 0.031721 0.026 Uiso 1 1 calc R U . . .
C13 C 0.119(2) 0.8017(15) 0.0711(11) 0.021(3) Uani 1 1 d . U . . .
C14 C 0.171(2) 0.7449(16) 0.1318(10) 0.018(3) Uani 1 1 d . U . . .
H14 H 0.237672 0.680985 0.130665 0.022 Uiso 1 1 calc R U . . .
C15 C 0.131(2) 0.7758(15) 0.1921(11) 0.020(3) Uani 1 1 d . U . . .
H15 H 0.168587 0.734042 0.233005 0.024 Uiso 1 1 calc R U . . .
C16 C 0.156(3) 0.7611(15) -0.0125(11) 0.026(4) Uani 1 1 d . U . . .
H16A H 0.169179 0.680820 -0.013712 0.039 Uiso 1 1 calc R U . . .
H16B H 0.256668 0.796889 -0.022132 0.039 Uiso 1 1 calc R U . . .
H16C H 0.061274 0.783185 -0.047837 0.039 Uiso 1 1 calc R U . . .
Br1 Br -0.1347(3) 1.05664(17) 0.14992(13) 0.0304(5) Uani 1 1 d . . . . .
N2 N 0.269(2) 0.2263(16) 0.1513(10) 0.033(4) Uani 1 1 d . . . . .
H2 H 0.297323 0.225654 0.109757 0.039 Uiso 1 1 calc R U . . .
C21 C 0.303(2) 0.1408(17) 0.1929(12) 0.023(4) Uani 1 1 d . U . . .
C22 C 0.265(2) 0.1390(18) 0.2572(13) 0.029(3) Uani 1 1 d . U . . .
H22 H 0.294800 0.076934 0.286379 0.035 Uiso 1 1 calc R U . . .
C23 C 0.184(2) 0.2265(19) 0.2810(12) 0.031(3) Uani 1 1 d . U . . .
C24 C 0.144(3) 0.3216(18) 0.2360(13) 0.034(6) Uani 1 1 d . . . . .
H24 H 0.087410 0.383928 0.250016 0.041 Uiso 1 1 calc R U . . .
C25 C 0.191(3) 0.3166(19) 0.1731(12) 0.028(5) Uani 1 1 d . . . . .
H25 H 0.168765 0.378025 0.142674 0.033 Uiso 1 1 calc R U . . .
C26 C 0.142(3) 0.232(2) 0.3518(12) 0.035(4) Uani 1 1 d . U . . .
H26A H 0.124964 0.309190 0.363848 0.052 Uiso 1 1 calc R U . . .
H26B H 0.233633 0.200917 0.385287 0.052 Uiso 1 1 calc R U . . .
H26C H 0.040818 0.189870 0.353160 0.052 Uiso 1 1 calc R U . . .
Br2 Br 0.4166(3) 0.0228(2) 0.16023(15) 0.0423(7) Uani 1 1 d . . . . .
N3 N 0.7907(17) 0.2355(14) 0.4886(8) 0.018(2) Uani 1 1 d . U . . .
H3 H 0.838988 0.297620 0.480090 0.022 Uiso 1 1 calc R U . . .
C31 C 0.694(2) 0.1817(16) 0.4356(11) 0.019(3) Uani 1 1 d . U . . .
C32 C 0.614(2) 0.0872(16) 0.4470(11) 0.020(3) Uani 1 1 d . U . . .
H32 H 0.540760 0.051581 0.410562 0.025 Uiso 1 1 calc R U . . .
C33 C 0.643(2) 0.0437(16) 0.5156(11) 0.020(3) Uani 1 1 d . U . . .
C34 C 0.742(2) 0.1019(16) 0.5660(11) 0.022(3) Uani 1 1 d . U . . .
H34 H 0.760235 0.074125 0.612173 0.026 Uiso 1 1 calc R U . . .
C35 C 0.814(2) 0.1966(17) 0.5531(11) 0.020(3) Uani 1 1 d . U . . .
H35 H 0.881436 0.235672 0.589700 0.024 Uiso 1 1 calc R U . . .
C36 C 0.562(2) -0.0606(16) 0.5326(11) 0.023(4) Uani 1 1 d . U . . .
H36A H 0.548701 -0.059481 0.581533 0.034 Uiso 1 1 calc R U . . .
H36B H 0.630576 -0.123699 0.524373 0.034 Uiso 1 1 calc R U . . .
H36C H 0.452439 -0.067115 0.503053 0.034 Uiso 1 1 calc R U . . .
Br3 Br 0.6722(3) 0.2447(2) 0.34735(12) 0.0340(5) Uani 1 1 d . . . . .
O1 O 0.324(2) 0.2373(17) 0.0221(10) 0.062(5) Uani 1 1 d . U . . .
O2 O 0.9599(17) 0.4265(12) 0.4779(9) 0.032(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Br11 2.736(2) . yes
Bi1 Br12 2.860(2) . yes
Bi1 Br13 2.7419(19) . yes
Bi1 Br14 3.042(2) . yes
Bi1 Br15 2.908(2) . yes
Bi1 Br16 2.988(2) . yes
Bi2 Br14 3.0208(19) . yes
Bi2 Br15 3.0836(19) . yes
Bi2 Br16 3.017(2) . yes
Bi2 Br17 2.723(2) . yes
Bi2 Br18 2.6928(19) . yes
Bi2 Br19 2.734(2) . yes
N1 H1 0.8800 . ?
N1 C11 1.29(2) . ?
N1 C15 1.37(2) . ?
C11 C12 1.42(3) . ?
C11 Br1 1.893(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.44(3) . ?
C13 C14 1.37(3) . ?
C13 C16 1.78(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.33(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N2 H2 0.8800 . ?
N2 C21 1.32(3) . ?
N2 C25 1.37(3) . ?
C21 C22 1.34(3) . ?
C21 Br2 1.88(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.38(3) . ?
C23 C24 1.45(3) . ?
C23 C26 1.48(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.35(3) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N3 H3 0.8800 . ?
N3 C31 1.36(2) . ?
N3 C35 1.33(2) . ?
C31 C32 1.36(3) . ?
C31 Br3 1.87(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.42(3) . ?
C33 C34 1.36(3) . ?
C33 C36 1.49(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.34(3) . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br11 Bi1 Br12 90.42(6) . . yes
Br11 Bi1 Br13 92.91(6) . . yes
Br11 Bi1 Br14 168.12(6) . . yes
Br11 Bi1 Br15 96.05(6) . . yes
Br11 Bi1 Br16 86.88(6) . . yes
Br12 Bi1 Br14 90.90(6) . . yes
Br12 Bi1 Br15 172.48(6) . . yes
Br12 Bi1 Br16 94.17(6) . . yes
Br13 Bi1 Br12 93.48(6) . . yes
Br13 Bi1 Br14 98.78(6) . . yes
Br13 Bi1 Br15 90.03(6) . . yes
Br13 Bi1 Br16 172.34(6) . . yes
Br15 Bi1 Br14 81.98(6) . . yes
Br15 Bi1 Br16 82.38(6) . . yes
Br16 Bi1 Br14 81.25(6) . . yes
Br14 Bi2 Br15 79.51(5) . . yes
Br16 Bi2 Br14 81.14(6) . . yes
Br16 Bi2 Br15 79.07(6) . . yes
Br17 Bi2 Br14 172.72(6) . . yes
Br17 Bi2 Br15 94.07(6) . . yes
Br17 Bi2 Br16 94.35(6) . . yes
Br17 Bi2 Br19 92.92(7) . . yes
Br18 Bi2 Br14 91.26(6) . . yes
Br18 Bi2 Br15 166.63(6) . . yes
Br18 Bi2 Br16 90.04(7) . . yes
Br18 Bi2 Br17 94.47(6) . . yes
Br18 Bi2 Br19 92.77(8) . . yes
Br19 Bi2 Br14 91.28(6) . . yes
Br19 Bi2 Br15 97.04(7) . . yes
Br19 Bi2 Br16 171.97(7) . . yes
Bi2 Br14 Bi1 82.28(5) . . yes
Bi1 Br15 Bi2 83.42(5) . . yes
Bi1 Br16 Bi2 83.25(5) . . yes
C11 N1 H1 119.5 . . ?
C11 N1 C15 121.1(18) . . ?
C15 N1 H1 119.5 . . ?
N1 C11 C12 123.6(18) . . ?
N1 C11 Br1 118.0(15) . . ?
C12 C11 Br1 118.4(15) . . ?
C11 C12 H12 122.8 . . ?
C11 C12 C13 114.3(19) . . ?
C13 C12 H12 122.8 . . ?
C12 C13 C16 115.7(17) . . ?
C14 C13 C12 118.6(19) . . ?
C14 C13 C16 125.4(16) . . ?
C13 C14 H14 118.7 . . ?
C15 C14 C13 122.6(18) . . ?
C15 C14 H14 118.7 . . ?
N1 C15 H15 120.2 . . ?
C14 C15 N1 119.6(19) . . ?
C14 C15 H15 120.2 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 N2 H2 120.2 . . ?
C21 N2 C25 119.6(19) . . ?
C25 N2 H2 120.2 . . ?
N2 C21 C22 122(2) . . ?
N2 C21 Br2 116.8(17) . . ?
C22 C21 Br2 120.9(17) . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120(2) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 119(2) . . ?
C22 C23 C26 124(2) . . ?
C24 C23 C26 117.7(19) . . ?
C23 C24 H24 121.8 . . ?
C25 C24 C23 116(2) . . ?
C25 C24 H24 121.8 . . ?
N2 C25 H25 118.7 . . ?
C24 C25 N2 123(2) . . ?
C24 C25 H25 118.7 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C31 N3 H3 119.2 . . ?
C35 N3 H3 119.2 . . ?
C35 N3 C31 121.5(18) . . ?
N3 C31 Br3 117.3(14) . . ?
C32 C31 N3 121.0(19) . . ?
C32 C31 Br3 121.7(16) . . ?
C31 C32 H32 121.3 . . ?
C31 C32 C33 117.5(19) . . ?
C33 C32 H32 121.3 . . ?
C32 C33 C36 121.1(18) . . ?
C34 C33 C32 118.2(18) . . ?
C34 C33 C36 120.7(19) . . ?
C33 C34 H34 118.7 . . ?
C35 C34 C33 123(2) . . ?
C35 C34 H34 118.7 . . ?
N3 C35 C34 119(2) . . ?
N3 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

_refine_diff_density_max         1.564
_refine_diff_density_min         -2.303
_refine_diff_density_rms         0.281

####################################################################### 
# 
# 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_IG338
_database_code_depnum_ccdc_archive 'CCDC 1863742'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H12 Bi Br2 Cl5 N2 O'
_chemical_formula_weight         722.27

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.5904(7)
_cell_length_b                   7.6333(4)
_cell_length_c                   21.9998(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.548(5)
_cell_angle_gamma                90
_cell_volume                     1933.69(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2606
_cell_measurement_theta_min      4.54
_cell_measurement_theta_max      28.80

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.481
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    13.939
_shelx_estimated_absorpt_T_min   0.042
_shelx_estimated_absorpt_T_max   0.158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.35970
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            10104
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.476
_diffrn_reflns_theta_max         28.909
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4309
_reflns_number_gt                3696
_reflns_threshold_expression     >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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_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)+(0.0274P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4309
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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 0.08584(2) 0.51778(3) 0.19579(2) 0.00826(8) Uani 1 1 d . . . . .
Cl1 Cl -0.03471(13) 0.26992(19) 0.14099(6) 0.0179(3) Uani 1 1 d . . . . .
Cl2 Cl -0.03385(15) 0.5042(2) 0.28885(7) 0.0255(4) Uani 1 1 d . . . . .
Cl3 Cl -0.05474(13) 0.75351(19) 0.14563(7) 0.0190(3) Uani 1 1 d . . . . .
Cl4 Cl 0.21550(13) 0.52960(19) 0.09623(7) 0.0148(3) Uani 1 1 d . . . . .
Cl5 Cl 0.25122(14) 0.2725(2) 0.25123(7) 0.0260(4) Uani 1 1 d . . . . .
N1 N 0.3634(4) 0.4126(7) 0.4575(2) 0.0207(12) Uani 1 1 d . . . . .
H1 H 0.428466 0.353078 0.457801 0.025 Uiso 1 1 calc R U . . .
C11 C 0.3152(5) 0.4251(8) 0.5096(3) 0.0195(14) Uani 1 1 d . . . . .
H11 H 0.350814 0.371744 0.546002 0.023 Uiso 1 1 calc R U . . .
C12 C 0.2140(6) 0.5158(8) 0.5095(3) 0.0167(14) Uani 1 1 d . . . . .
C13 C 0.1634(5) 0.5957(8) 0.4566(3) 0.0211(14) Uani 1 1 d . . . . .
H13 H 0.093239 0.660101 0.456490 0.025 Uiso 1 1 calc R U . . .
C14 C 0.2168(6) 0.5801(8) 0.4039(3) 0.0237(15) Uani 1 1 d . . . . .
H14 H 0.183949 0.634118 0.367059 0.028 Uiso 1 1 calc R U . . .
C15 C 0.3183(7) 0.4855(8) 0.4052(3) 0.0246(16) Uani 1 1 d . . . . .
H15 H 0.355553 0.472465 0.369226 0.029 Uiso 1 1 calc R U . . .
Br1 Br 0.14512(7) 0.52585(9) 0.58292(3) 0.03103(19) Uani 1 1 d . . . . .
N2 N 0.4630(5) 0.5396(7) 0.1730(2) 0.0229(13) Uani 1 1 d . . . . .
H2 H 0.388050 0.559130 0.172693 0.027 Uiso 1 1 calc R U . . .
C21 C 0.5072(6) 0.5281(8) 0.1187(3) 0.0230(15) Uani 1 1 d . . . . .
H21 H 0.458202 0.540901 0.081269 0.028 Uiso 1 1 calc R U . . .
C22 C 0.6242(6) 0.4976(7) 0.1185(3) 0.0156(14) Uani 1 1 d . . . . .
C23 C 0.6943(6) 0.4806(8) 0.1746(3) 0.0205(15) Uani 1 1 d . . . . .
H23 H 0.775330 0.460206 0.175561 0.025 Uiso 1 1 calc R U . . .
C24 C 0.6443(6) 0.4938(8) 0.2281(3) 0.0236(16) Uani 1 1 d . . . . .
H24 H 0.691113 0.482772 0.266305 0.028 Uiso 1 1 calc R U . . .
C25 C 0.5272(6) 0.5229(8) 0.2268(3) 0.0202(15) Uani 1 1 d . . . . .
H25 H 0.492531 0.530988 0.263772 0.024 Uiso 1 1 calc R U . . .
Br2 Br 0.68496(6) 0.48196(8) 0.04368(3) 0.02104(16) Uani 1 1 d . . . . .
O1 O 0.5535(4) 0.2066(6) 0.49562(18) 0.0247(10) 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 Cl1 2.5692(14) . yes
Bi1 Cl2 2.6028(16) . yes
Bi1 Cl3 2.5884(14) . yes
Bi1 Cl4 2.7954(15) . yes
Bi1 Cl5 2.8523(14) . yes
Bi1 Cl5 2.8640(14) 2 yes
N1 H1 0.8800 . ?
N1 C11 1.333(7) . ?
N1 C15 1.330(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.362(9) . ?
C12 C13 1.385(9) . ?
C12 Br1 1.883(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(10) . ?
C15 H15 0.9500 . ?
N2 H2 0.8800 . ?
N2 C21 1.357(8) . ?
N2 C25 1.330(8) . ?
C21 H21 0.9500 . ?
C21 C22 1.376(9) . ?
C22 C23 1.404(9) . ?
C22 Br2 1.866(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.374(9) . ?
C24 H24 0.9500 . ?
C24 C25 1.372(10) . ?
C25 H25 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
Cl1 Bi1 Cl2 91.70(5) . . yes
Cl1 Bi1 Cl3 91.70(5) . . yes
Cl1 Bi1 Cl4 88.18(5) . . yes
Cl1 Bi1 Cl5 91.15(5) . . yes
Cl1 Bi1 Cl5 171.46(5) . 2 yes
Cl2 Bi1 Cl4 179.48(5) . . yes
Cl2 Bi1 Cl5 91.72(5) . . yes
Cl2 Bi1 Cl5 95.32(5) . 2 yes
Cl3 Bi1 Cl2 89.82(5) . . yes
Cl3 Bi1 Cl4 90.69(4) . . yes
Cl3 Bi1 Cl5 93.18(5) . 2 yes
Cl3 Bi1 Cl5 176.71(5) . . yes
Cl4 Bi1 Cl5 84.75(4) . 2 yes
Cl4 Bi1 Cl5 87.77(4) . . yes
Cl5 Bi1 Cl5 83.790(7) . 2 yes
Bi1 Cl5 Bi1 178.17(7) . 2_545 yes
C11 N1 H1 118.3 . . ?
C15 N1 H1 118.3 . . ?
C15 N1 C11 123.4(6) . . ?
N1 C11 H11 120.6 . . ?
N1 C11 C12 118.7(6) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C13 120.4(6) . . ?
C11 C12 Br1 118.0(5) . . ?
C13 C12 Br1 121.6(5) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.7(6) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 120.3 . . ?
C15 C14 C13 119.4(6) . . ?
C15 C14 H14 120.3 . . ?
N1 C15 C14 119.2(6) . . ?
N1 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C21 N2 H2 118.4 . . ?
C25 N2 H2 118.4 . . ?
C25 N2 C21 123.2(6) . . ?
N2 C21 H21 120.5 . . ?
N2 C21 C22 119.0(6) . . ?
C22 C21 H21 120.5 . . ?
C21 C22 C23 119.0(6) . . ?
C21 C22 Br2 118.9(5) . . ?
C23 C22 Br2 122.1(5) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 C22 119.3(6) . . ?
C24 C23 H23 120.4 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.4(6) . . ?
C25 C24 H24 119.8 . . ?
N2 C25 C24 119.2(6) . . ?
N2 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?

_refine_diff_density_max         2.309
_refine_diff_density_min         -2.222
_refine_diff_density_rms         0.233

####################################################################### 
# 
# 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_SA1777
_database_code_depnum_ccdc_archive 'CCDC 1863745'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Bi2 Br4 Cl10 N4'
_chemical_formula_weight         1408.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.8204(4)
_cell_length_b                   10.4344(4)
_cell_length_c                   10.4924(4)
_cell_angle_alpha                99.470(3)
_cell_angle_beta                 97.092(4)
_cell_angle_gamma                108.757(4)
_cell_volume                     885.70(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2671
_cell_measurement_theta_min      3.77
_cell_measurement_theta_max      28.81

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.641
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    15.208
_shelx_estimated_absorpt_T_min   0.059
_shelx_estimated_absorpt_T_max   0.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40892
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            7177
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.320
_diffrn_reflns_theta_max         28.951
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3893
_reflns_number_gt                3444
_reflns_threshold_expression     >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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_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)+(0.0133P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3893
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0627
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.42261(3) 0.62936(2) 0.64103(2) 0.01136(8) Uani 1 1 d . . . . .
Cl1 Cl 0.45772(18) 0.79954(16) 0.46877(16) 0.0165(3) Uani 1 1 d . . . . .
Cl2 Cl 0.13546(18) 0.62783(17) 0.65958(17) 0.0188(4) Uani 1 1 d . . . . .
Cl3 Cl 0.40345(18) 0.46404(16) 0.81436(16) 0.0163(3) Uani 1 1 d . . . . .
Cl4 Cl 0.56369(18) 0.84667(16) 0.83450(17) 0.0190(4) Uani 1 1 d . . . . .
Cl5 Cl 0.71820(17) 0.59453(16) 0.58745(17) 0.0169(4) Uani 1 1 d . . . . .
N1 N 0.1428(6) 0.8652(5) 0.4165(5) 0.0159(12) Uani 1 1 d . . . . .
H1 H 0.224078 0.843911 0.453377 0.019 Uiso 1 1 calc R U . . .
C11 C -0.0074(8) 0.8011(7) 0.4370(7) 0.0194(16) Uani 1 1 d . . . . .
H11 H -0.025186 0.733434 0.489272 0.023 Uiso 1 1 calc R U . . .
C12 C -0.1353(7) 0.8341(6) 0.3817(6) 0.0138(14) Uani 1 1 d . . . . .
H12 H -0.242645 0.790498 0.395395 0.017 Uiso 1 1 calc R U . . .
C13 C -0.1037(7) 0.9327(6) 0.3056(7) 0.0151(14) Uani 1 1 d . . . . .
C14 C 0.0504(7) 0.9953(7) 0.2852(6) 0.0174(15) Uani 1 1 d . . . . .
H14 H 0.071322 1.062173 0.232124 0.021 Uiso 1 1 calc R U . . .
C15 C 0.1742(8) 0.9592(7) 0.3432(7) 0.0186(15) Uani 1 1 d . . . . .
H15 H 0.282511 1.001640 0.330873 0.022 Uiso 1 1 calc R U . . .
Br1 Br -0.27721(8) 0.98116(7) 0.23086(7) 0.02194(17) Uani 1 1 d . . . . .
N2 N 0.7106(6) 0.3779(5) 0.8528(5) 0.0150(12) Uani 1 1 d . . . . .
H2 H 0.634312 0.407573 0.820840 0.018 Uiso 1 1 calc R U . . .
C21 C 0.8535(8) 0.4131(6) 0.8103(7) 0.0177(15) Uani 1 1 d . . . . .
H21 H 0.868777 0.465353 0.743845 0.021 Uiso 1 1 calc R U . . .
C22 C 0.9748(8) 0.3738(6) 0.8624(7) 0.0162(15) Uani 1 1 d . . . . .
H22 H 1.077635 0.401612 0.836099 0.019 Uiso 1 1 calc R U . . .
C23 C 0.9474(7) 0.2928(6) 0.9542(7) 0.0152(14) Uani 1 1 d . . . . .
C24 C 0.7978(8) 0.2544(7) 0.9952(7) 0.0183(15) Uani 1 1 d . . . . .
H24 H 0.777585 0.198460 1.058401 0.022 Uiso 1 1 calc R U . . .
C25 C 0.6811(8) 0.3002(7) 0.9411(7) 0.0183(15) Uani 1 1 d . . . . .
H25 H 0.577926 0.276085 0.967042 0.022 Uiso 1 1 calc R U . . .
Br2 Br 1.11628(8) 0.23948(7) 1.03063(7) 0.02103(16) 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 Cl1 2.7123(16) . yes
Bi1 Cl2 2.5592(14) . yes
Bi1 Cl3 2.6893(16) . yes
Bi1 Cl4 2.6187(17) . yes
Bi1 Cl5 2.8548(14) . yes
Bi1 Cl5 2.8815(17) 2_666 yes
N1 H1 0.8800 . ?
N1 C11 1.340(8) . ?
N1 C15 1.326(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.371(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(9) . ?
C13 C14 1.367(8) . ?
C13 Br1 1.883(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.371(9) . ?
C15 H15 0.9500 . ?
N2 H2 0.8800 . ?
N2 C21 1.348(8) . ?
N2 C25 1.323(8) . ?
C21 H21 0.9500 . ?
C21 C22 1.351(8) . ?
C22 H22 0.9500 . ?
C22 C23 1.376(9) . ?
C23 C24 1.394(9) . ?
C23 Br2 1.886(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.368(9) . ?
C25 H25 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
Cl1 Bi1 Cl5 85.88(5) . 2_666 yes
Cl1 Bi1 Cl5 87.15(4) . . yes
Cl2 Bi1 Cl1 92.90(5) . . yes
Cl2 Bi1 Cl3 89.70(5) . . yes
Cl2 Bi1 Cl4 93.44(5) . . yes
Cl2 Bi1 Cl5 88.79(5) . 2_666 yes
Cl2 Bi1 Cl5 171.09(5) . . yes
Cl3 Bi1 Cl1 177.25(4) . . yes
Cl3 Bi1 Cl5 90.43(4) . . yes
Cl3 Bi1 Cl5 95.10(5) . 2_666 yes
Cl4 Bi1 Cl1 89.29(5) . . yes
Cl4 Bi1 Cl3 89.64(5) . . yes
Cl4 Bi1 Cl5 95.47(5) . . yes
Cl4 Bi1 Cl5 174.78(5) . 2_666 yes
Cl5 Bi1 Cl5 82.33(5) . 2_666 yes
Bi1 Cl5 Bi1 97.67(5) . 2_666 yes
C11 N1 H1 118.6 . . ?
C15 N1 H1 118.6 . . ?
C15 N1 C11 122.8(6) . . ?
N1 C11 H11 120.3 . . ?
N1 C11 C12 119.5(6) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.9 . . ?
C11 C12 C13 118.2(6) . . ?
C13 C12 H12 120.9 . . ?
C12 C13 Br1 118.9(5) . . ?
C14 C13 C12 121.1(6) . . ?
C14 C13 Br1 120.1(5) . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.4(6) . . ?
C15 C14 H14 120.8 . . ?
N1 C15 C14 120.0(6) . . ?
N1 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C21 N2 H2 118.8 . . ?
C25 N2 H2 118.8 . . ?
C25 N2 C21 122.3(5) . . ?
N2 C21 H21 120.1 . . ?
N2 C21 C22 119.8(6) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 120.5 . . ?
C21 C22 C23 119.1(6) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 C24 120.6(6) . . ?
C22 C23 Br2 119.8(5) . . ?
C24 C23 Br2 119.6(5) . . ?
C23 C24 H24 121.2 . . ?
C25 C24 C23 117.6(6) . . ?
C25 C24 H24 121.2 . . ?
N2 C25 C24 120.6(6) . . ?
N2 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?

_refine_diff_density_max         1.830
_refine_diff_density_min         -1.450
_refine_diff_density_rms         0.240

