# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_TDCB
_database_code_depnum_ccdc_archive 'CCDC 1031018'
_audit_update_record             
;
2014-10-26 deposited with the CCDC.
2015-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Bi Cl6, 3(C4 H12 N)'
_chemical_formula_sum            'C12 H36 Bi Cl6 N3'
_chemical_formula_weight         644.12

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

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'R 3 c'
_symmetry_space_group_name_Hall  'R 3 -2"c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'x, x-y, z+1/2'
'-x+y, y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'

_cell_length_a                   14.699(4)
_cell_length_b                   14.699(4)
_cell_length_c                   19.102(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     3574.2(17)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.49

_exptl_crystal_description       bulk
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1884
_exptl_absorpt_coefficient_mu    8.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1406
_exptl_absorpt_correction_T_max  0.1956
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker,2009)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12907
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         27.49
_reflns_number_total             1816
_reflns_number_gt                1807
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00115(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.009(6)
_refine_ls_number_reflns         1816
_refine_ls_number_parameters     70
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0109
_refine_ls_R_factor_gt           0.0109
_refine_ls_wR_factor_ref         0.0295
_refine_ls_wR_factor_gt          0.0295
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.25301(9) 0.88619(10) 0.97588(6) 0.0146(3) Uani 1 1 d . . .
H3A H 0.2159 0.8174 0.9867 0.018 Uiso 1 1 d R . .
H3B H 0.2084 0.9043 0.9567 0.018 Uiso 1 1 d R . .
C1 C 0.34057(13) 1.06365(13) 1.03123(10) 0.0230(3) Uani 1 1 d . . .
H1A H 0.2852 1.0766 1.0176 0.035 Uiso 1 1 calc R . .
H1B H 0.3932 1.0883 0.9953 0.035 Uiso 1 1 calc R . .
H1C H 0.3715 1.1001 1.0741 0.035 Uiso 1 1 calc R . .
C2 C 0.29633(13) 0.94729(13) 1.04181(8) 0.0204(3) Uani 1 1 d . . .
H2A H 0.3513 0.9352 1.0595 0.024 Uiso 1 1 calc R . .
H2B H 0.2411 0.9222 1.0767 0.024 Uiso 1 1 calc R . .
C4 C 0.33447(12) 0.90217(13) 0.92242(8) 0.0188(3) Uani 1 1 d . . .
H4A H 0.3922 0.8996 0.9451 0.023 Uiso 1 1 calc R . .
H4B H 0.3620 0.9708 0.9011 0.023 Uiso 1 1 calc R . .
C6 C 0.28757(16) 0.81806(14) 0.86636(9) 0.0260(4) Uani 1 1 d . . .
H6A H 0.2313 0.8215 0.8433 0.039 Uiso 1 1 calc R . .
H6B H 0.2609 0.7502 0.8875 0.039 Uiso 1 1 calc R . .
H6C H 0.3408 0.8293 0.8327 0.039 Uiso 1 1 calc R . .
Bi1 Bi 0.0000 1.0000 0.95845(4) 0.01017(5) Uani 1 3 d S . .
Cl2 Cl 0.15648(3) 0.99315(3) 0.872649(17) 0.01561(8) Uani 1 1 d . . .
Cl3 Cl 0.02079(3) 0.86414(3) 1.033565(18) 0.01856(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0129(6) 0.0131(6) 0.0181(6) 0.0025(5) 0.0002(5) 0.0067(5)
C1 0.0229(8) 0.0210(9) 0.0262(8) -0.0043(7) -0.0041(7) 0.0118(8)
C2 0.0213(7) 0.0242(8) 0.0176(7) 0.0023(7) 0.0008(7) 0.0128(6)
C4 0.0154(8) 0.0220(8) 0.0184(7) 0.0030(6) 0.0032(6) 0.0089(7)
C6 0.0309(10) 0.0237(9) 0.0222(8) 0.0008(7) 0.0057(7) 0.0127(8)
Bi1 0.01004(6) 0.01004(6) 0.01044(7) 0.000 0.000 0.00502(3)
Cl2 0.01690(18) 0.01532(18) 0.01568(18) 0.00323(14) 0.00369(14) 0.00885(16)
Cl3 0.01979(18) 0.01779(17) 0.01869(19) 0.00586(15) 0.00102(15) 0.00983(16)

_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
N1 C2 1.492(2) . ?
N1 C4 1.5001(19) . ?
N1 H3A 0.9001 . ?
N1 H3B 0.9000 . ?
C1 C2 1.509(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C6 1.516(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
Bi1 Cl3 2.5981(7) 2_675 ?
Bi1 Cl3 2.5981(7) 3_465 ?
Bi1 Cl3 2.5981(7) . ?
Bi1 Cl2 2.8667(8) 3_465 ?
Bi1 Cl2 2.8667(8) 2_675 ?
Bi1 Cl2 2.8667(8) . ?

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
C2 N1 C4 114.41(12) . . ?
C2 N1 H3A 108.6 . . ?
C4 N1 H3A 108.7 . . ?
C2 N1 H3B 108.7 . . ?
C4 N1 H3B 108.7 . . ?
H3A N1 H3B 107.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 112.44(12) . . ?
N1 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N1 C4 C6 110.57(13) . . ?
N1 C4 H4A 109.5 . . ?
C6 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
C6 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Cl3 Bi1 Cl3 92.43(2) 2_675 3_465 ?
Cl3 Bi1 Cl3 92.43(2) 2_675 . ?
Cl3 Bi1 Cl3 92.43(2) 3_465 . ?
Cl3 Bi1 Cl2 172.324(13) 2_675 3_465 ?
Cl3 Bi1 Cl2 83.339(19) 3_465 3_465 ?
Cl3 Bi1 Cl2 94.140(18) . 3_465 ?
Cl3 Bi1 Cl2 83.339(18) 2_675 2_675 ?
Cl3 Bi1 Cl2 94.141(18) 3_465 2_675 ?
Cl3 Bi1 Cl2 172.323(13) . 2_675 ?
Cl2 Bi1 Cl2 90.56(2) 3_465 2_675 ?
Cl3 Bi1 Cl2 94.142(18) 2_675 . ?
Cl3 Bi1 Cl2 172.324(13) 3_465 . ?
Cl3 Bi1 Cl2 83.339(18) . . ?
Cl2 Bi1 Cl2 90.56(2) 3_465 . ?
Cl2 Bi1 Cl2 90.56(2) 2_675 . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.060
