# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_sa1160
_database_code_depnum_ccdc_archive 'CCDC 1474709'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 Bi2 Br11 N3'
_chemical_formula_weight         1537.29

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'
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           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.8459(2)
_cell_length_b                   23.3803(4)
_cell_length_c                   9.4868(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.370(3)
_cell_angle_gamma                90
_cell_volume                     1631.43(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4300
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      28.96

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.129
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    24.254
_shelx_estimated_absorpt_T_min   0.112
_shelx_estimated_absorpt_T_max   0.530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36677
_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_ambient_temperature      130(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            8267
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.272
_diffrn_reflns_theta_max         29.535
_diffrn_reflns_theta_full        26.500
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3879
_reflns_number_gt                3420
_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    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'

_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)+(0.0237P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3879
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0556
_refine_ls_wR_factor_gt          0.0532
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.002
_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 0.35506(2) 0.33456(2) 0.65779(2) 0.01627(6) Uani 1 1 d . . . . .
Br1 Br 0.16200(6) 0.40011(2) 0.78404(5) 0.02838(12) Uani 1 1 d . . . . .
Br2 Br 0.24951(7) 0.40680(2) 0.40986(5) 0.02986(13) Uani 1 1 d . . . . .
Br3 Br 0.65487(6) 0.39935(2) 0.78716(6) 0.02973(13) Uani 1 1 d . . . . .
Br4 Br 0.55570(8) 0.2500 0.52857(7) 0.02390(15) Uani 1 2 d S T P . .
Br5 Br 0.46371(9) 0.2500 0.91173(7) 0.02598(16) Uani 1 2 d S T P . .
Br6 Br 0.04435(8) 0.2500 0.52939(7) 0.02356(15) Uani 1 2 d S T P . .
Br7 Br 0.05307(6) 0.47245(2) 0.10820(5) 0.02498(11) Uani 1 1 d . . . . .
N1 N 0.2327(7) 0.6154(3) 0.5810(6) 0.0582(17) Uani 1 1 d . . . . .
H1 H 0.1626 0.6367 0.5071 0.070 Uiso 1 1 calc R U . . .
C11 C 0.3236(8) 0.6392(3) 0.7209(7) 0.0475(16) Uani 1 1 d . . . . .
H11 H 0.3104 0.6786 0.7391 0.057 Uiso 1 1 calc R U . . .
C12 C 0.4322(8) 0.6047(4) 0.8317(7) 0.056(2) Uani 1 1 d . . . . .
H12 H 0.4965 0.6199 0.9285 0.068 Uiso 1 1 calc R U . . .
C13 C 0.4478(9) 0.5478(4) 0.8022(8) 0.061(2) Uani 1 1 d . . . . .
H13 H 0.5241 0.5235 0.8782 0.073 Uiso 1 1 calc R U . . .
C14 C 0.3563(7) 0.5273(3) 0.6676(7) 0.0354(13) Uani 1 1 d . . . . .
H14 H 0.3662 0.4877 0.6492 0.042 Uiso 1 1 calc R U . . .
C15 C 0.2530(8) 0.5592(3) 0.5593(7) 0.0424(15) Uani 1 1 d . . . . .
H15 H 0.1909 0.5427 0.4636 0.051 Uiso 1 1 calc R U . . .
N2 N 0.9482(6) 0.2220(2) 0.9039(5) 0.0377(13) Uani 0.5 1 d . . P . .
H2 H 0.8915 0.2036 0.8196 0.045 Uiso 1 1 calc R U . . .
C21 C 0.9482(6) 0.2220(2) 0.9039(5) 0.0377(13) Uani 0.5 1 d . . P . .
C22 C 1.0315(9) 0.1924(3) 1.0279(7) 0.0490(16) Uani 1 1 d . . . . .
H22 H 1.0272 0.1518 1.0266 0.059 Uiso 1 1 calc R U . . .
C23 C 1.1235(10) 0.2210(3) 1.1573(6) 0.066(2) Uani 1 1 d . . . . .
H23 H 1.1869 0.2004 1.2466 0.079 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 Br1 2.7094(5) . yes
Bi1 Br2 2.7776(5) . yes
Bi1 Br3 2.7064(5) . yes
Bi1 Br4 3.0386(5) . yes
Bi1 Br5 3.0015(5) . yes
Bi1 Br6 3.0444(5) . yes
Br4 Bi1 3.0386(5) 4_565 ?
Br5 Bi1 3.0015(5) 4_565 ?
Br6 Bi1 3.0443(5) 4_565 ?
Br7 Br7 2.3190(9) 3_565 yes
N1 H1 0.8800 . ?
N1 C11 1.386(8) . ?
N1 C15 1.348(8) . ?
C11 H11 0.9500 . ?
C11 C12 1.363(9) . ?
C12 H12 0.9500 . ?
C12 C13 1.373(10) . ?
C13 H13 0.9500 . ?
C13 C14 1.318(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.299(8) . ?
C15 H15 0.9500 . ?
N2 H2 0.8800 . ?
N2 C21 1.308(10) 4_565 ?
N2 C22 1.325(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.362(8) . ?
C23 C23 1.357(14) 4_565 ?
C23 H23 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
Br1 Bi1 Br2 89.002(16) . . yes
Br1 Bi1 Br4 173.854(15) . . yes
Br1 Bi1 Br5 93.673(16) . . yes
Br1 Bi1 Br6 92.934(15) . . yes
Br2 Bi1 Br4 95.604(16) . . yes
Br2 Bi1 Br5 176.253(15) . . yes
Br2 Bi1 Br6 95.446(16) . . yes
Br3 Bi1 Br1 90.819(16) . . yes
Br3 Bi1 Br2 89.972(16) . . yes
Br3 Bi1 Br4 93.245(16) . . yes
Br3 Bi1 Br5 92.609(16) . . yes
Br3 Bi1 Br6 173.458(15) . . yes
Br4 Bi1 Br6 82.599(14) . . yes
Br5 Bi1 Br4 81.545(15) . . yes
Br5 Bi1 Br6 81.810(15) . . yes
Bi1 Br4 Bi1 81.179(16) 4_565 . yes
Bi1 Br5 Bi1 82.397(17) 4_565 . yes
Bi1 Br6 Bi1 80.993(15) 4_565 . yes
C11 N1 H1 120.4 . . ?
C15 N1 H1 120.4 . . ?
C15 N1 C11 119.3(6) . . ?
N1 C11 H11 120.8 . . ?
C12 C11 N1 118.4(6) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.5(6) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.5(6) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 118.8 . . ?
C15 C14 C13 122.4(6) . . ?
C15 C14 H14 118.8 . . ?
N1 C15 H15 119.6 . . ?
C14 C15 N1 120.9(6) . . ?
C14 C15 H15 119.6 . . ?
C21 N2 H2 119.3 4_565 . ?
C21 N2 C22 121.5(3) 4_565 . ?
C22 N2 H2 119.3 . . ?
N2 C22 H22 120.4 . . ?
N2 C22 C23 119.2(6) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 120.3 . . ?
C23 C23 C22 119.3(4) 4_565 . ?
C23 C23 H23 120.3 4_565 . ?

_refine_diff_density_max         1.274
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.179

