# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1
_database_code_depnum_ccdc_archive 'CCDC 1056757'
_audit_update_record             
;
2015-03-28 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H14 N2), Bi2 Cl10, 2(H2 O)'
_chemical_formula_sum            'C24 H32 Bi2 Cl10 N4 O2'
_chemical_formula_weight         1181.00

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9907(6)
_cell_length_b                   11.3474(6)
_cell_length_c                   15.5308(8)
_cell_angle_alpha                78.4430(10)
_cell_angle_beta                 85.2330(10)
_cell_angle_gamma                72.7580(10)
_cell_volume                     1811.81(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    10.467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2067
_exptl_absorpt_correction_T_max  0.3665
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex DUO CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 25
_diffrn_reflns_number            47738
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         27.48
_reflns_number_total             8297
_reflns_number_gt                7517
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0140P)²+0.4701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8297
_refine_ls_number_parameters     391
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0166
_refine_ls_R_factor_gt           0.0137
_refine_ls_wR_factor_ref         0.0347
_refine_ls_wR_factor_gt          0.0336
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.504728(6) 0.863728(6) -0.071917(4) 0.01308(2) Uani 1 1 d . . .
Cl1 Cl 0.45506(4) 0.70060(4) 0.07557(3) 0.02049(10) Uani 1 1 d . . .
N1 N 0.61970(15) 1.00315(15) 0.39010(11) 0.0196(3) Uani 1 1 d . . .
H1 H 0.6288 0.9410 0.3618 0.024 Uiso 1 1 calc R . .
C1 C 0.50758(19) 1.09440(19) 0.38649(13) 0.0221(4) Uani 1 1 d . . .
H1A H 0.4395 1.0909 0.3542 0.026 Uiso 1 1 calc R . .
Bi2 Bi 0.994729(6) 0.370975(6) 0.423159(4) 0.01259(2) Uani 1 1 d . . .
Cl2 Cl 0.35920(4) 0.80218(5) -0.16485(3) 0.02189(10) Uani 1 1 d . . .
N2 N 0.56631(16) 1.56332(16) 0.75515(11) 0.0212(4) Uani 1 1 d . . .
H2 H 0.5586 1.6235 0.7850 0.025 Uiso 1 1 calc R . .
C2 C 0.49267(18) 1.19228(18) 0.42984(12) 0.0199(4) Uani 1 1 d . . .
H2A H 0.4132 1.2554 0.4286 0.024 Uiso 1 1 calc R . .
Cl3 Cl 0.69239(4) 0.69048(5) -0.12208(3) 0.02301(10) Uani 1 1 d . . .
N3 N 0.86761(16) 0.47836(15) 0.12210(11) 0.0202(4) Uani 1 1 d . . .
H3 H 0.8549 0.5388 0.1525 0.024 Uiso 1 1 calc R . .
C3 C 0.59343(18) 1.19968(18) 0.47574(12) 0.0177(4) Uani 1 1 d . . .
Cl4 Cl 0.53051(4) 1.03211(4) -0.20892(3) 0.02066(10) Uani 1 1 d . . .
N4 N 0.96470(16) -0.06074(16) -0.26200(11) 0.0207(4) Uani 1 1 d . . .
H4 H 0.9725 -0.1199 -0.2928 0.025 Uiso 1 1 calc R . .
C4 C 0.70708(19) 1.10230(18) 0.47837(13) 0.0211(4) Uani 1 1 d . . .
H4A H 0.7772 1.1036 0.5097 0.025 Uiso 1 1 calc R . .
Cl5 Cl 0.69884(4) 0.93887(5) 0.01158(3) 0.02050(10) Uani 1 1 d . . .
C5 C 0.71732(19) 1.00485(18) 0.43564(13) 0.0213(4) Uani 1 1 d . . .
H5 H 0.7942 0.9381 0.4384 0.026 Uiso 1 1 calc R . .
Cl6 Cl 0.98865(4) 0.55748(4) 0.28386(3) 0.01975(10) Uani 1 1 d . . .
C6 C 0.46070(18) 1.54159(19) 0.73321(13) 0.0215(4) Uani 1 1 d . . .
H6 H 0.3792 1.5914 0.7491 0.026 Uiso 1 1 calc R . .
Cl7 Cl 0.84002(4) 0.30450(5) 0.33693(3) 0.02100(10) Uani 1 1 d . . .
C7 C 0.47060(19) 1.44726(19) 0.68779(13) 0.0216(4) Uani 1 1 d . . .
H7 H 0.3958 1.4325 0.6713 0.026 Uiso 1 1 calc R . .
Cl8 Cl 1.18110(4) 0.21375(5) 0.35426(3) 0.02387(11) Uani 1 1 d . . .
C8 C 0.5907(2) 1.37266(18) 0.66564(12) 0.0201(4) Uani 1 1 d . . .
Cl9 Cl 0.96644(5) 0.19870(5) 0.56264(3) 0.02355(10) Uani 1 1 d . . .
C9 C 0.69795(19) 1.40094(18) 0.68798(13) 0.0214(4) Uani 1 1 d . . .
H9 H 0.7807 1.3541 0.6718 0.026 Uiso 1 1 calc R . .
Cl10 Cl 0.80979(4) 0.56119(4) 0.50011(3) 0.02003(10) Uani 1 1 d . . .
C10 C 0.68363(19) 1.49639(19) 0.73323(13) 0.0221(4) Uani 1 1 d . . .
H10 H 0.7565 1.5152 0.7491 0.027 Uiso 1 1 calc R . .
C11 C 0.5804(2) 1.30876(18) 0.52027(13) 0.0215(4) Uani 1 1 d . . .
H11A H 0.4937 1.3675 0.5113 0.026 Uiso 1 1 calc R . .
H11B H 0.6424 1.3543 0.4933 0.026 Uiso 1 1 calc R . .
C12 C 0.6037(2) 1.26551(19) 0.61916(13) 0.0271(5) Uani 1 1 d . . .
H12A H 0.5421 1.2194 0.6457 0.033 Uiso 1 1 calc R . .
H12B H 0.6905 1.2068 0.6279 0.033 Uiso 1 1 calc R . .
C13 C 0.77279(19) 0.47652(18) 0.07410(13) 0.0212(4) Uani 1 1 d . . .
H13 H 0.6941 0.5408 0.0721 0.025 Uiso 1 1 calc R . .
C14 C 0.78966(18) 0.38131(18) 0.02764(13) 0.0206(4) Uani 1 1 d . . .
H14 H 0.7225 0.3799 -0.0065 0.025 Uiso 1 1 calc R . .
C15 C 0.90497(18) 0.28709(17) 0.03055(12) 0.0163(4) Uani 1 1 d . . .
C16 C 1.00270(18) 0.29556(19) 0.07873(13) 0.0215(4) Uani 1 1 d . . .
H16 H 1.0840 0.2353 0.0793 0.026 Uiso 1 1 calc R . .
C17 C 0.98151(19) 0.3912(2) 0.12550(13) 0.0239(4) Uani 1 1 d . . .
H17 H 1.0470 0.3956 0.1599 0.029 Uiso 1 1 calc R . .
C18 C 0.84832(19) -0.00344(19) -0.23224(14) 0.0237(4) Uani 1 1 d . . .
H18 H 0.7765 -0.0275 -0.2441 0.028 Uiso 1 1 calc R . .
C19 C 0.83332(19) 0.08944(19) -0.18495(13) 0.0233(4) Uani 1 1 d . . .
H19 H 0.7512 0.1298 -0.1634 0.028 Uiso 1 1 calc R . .
C20 C 0.9392(2) 0.12482(18) -0.16830(12) 0.0217(4) Uani 1 1 d . . .
C21 C 1.0584(2) 0.0611(2) -0.19956(13) 0.0255(4) Uani 1 1 d . . .
H21 H 1.1323 0.0819 -0.1882 0.031 Uiso 1 1 calc R . .
C22 C 1.06876(19) -0.03185(19) -0.24687(13) 0.0238(4) Uani 1 1 d . . .
H22 H 1.1496 -0.0751 -0.2686 0.029 Uiso 1 1 calc R . .
C23 C 0.9237(2) 0.18081(18) -0.01756(12) 0.0195(4) Uani 1 1 d . . .
H23A H 0.8541 0.1411 -0.0009 0.023 Uiso 1 1 calc R . .
H23B H 1.0054 0.1166 -0.0005 0.023 Uiso 1 1 calc R . .
C24 C 0.9250(2) 0.2273(2) -0.11730(13) 0.0300(5) Uani 1 1 d . . .
H24A H 0.8447 0.2939 -0.1336 0.036 Uiso 1 1 calc R . .
H24B H 0.9963 0.2648 -0.1337 0.036 Uiso 1 1 calc R . .
O1W O 0.71133(18) 0.78612(16) 0.33073(11) 0.0448(5) Uani 1 1 d D . .
O2W O 0.70610(14) 0.71038(14) 0.16857(10) 0.0250(3) Uani 1 1 d . . .
H1WA H 0.774(3) 0.737(2) 0.3529(17) 0.037 Uiso 1 1 d . . .
H2WA H 0.633(2) 0.709(2) 0.1646(16) 0.037 Uiso 1 1 d . . .
H1WB H 0.710(2) 0.774(2) 0.2808(12) 0.037 Uiso 1 1 d D . .
H2WB H 0.712(2) 0.774(2) 0.1311(17) 0.037 Uiso 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 Cl2 2.5650(5) . ?
Bi1 Cl3 2.5824(5) . ?
Bi1 Cl4 2.6173(5) . ?
Bi1 Cl1 2.7683(5) . ?
Bi1 Cl5 2.9022(5) 2_675 ?
Bi1 Cl5 2.9902(5) . ?
N1 C5 1.340(3) . ?
N1 C1 1.351(2) . ?
N1 H1 0.8800 . ?
C1 C2 1.374(3) . ?
C1 H1A 0.9500 . ?
Bi2 Cl8 2.5996(5) . ?
Bi2 Cl7 2.6072(5) . ?
Bi2 Cl9 2.6763(5) . ?
Bi2 Cl6 2.6962(5) . ?
Bi2 Cl10 2.8718(5) . ?
Bi2 Cl10 2.8986(5) 2_766 ?
N2 C6 1.339(3) . ?
N2 C10 1.344(3) . ?
N2 H2 0.8800 . ?
C2 C3 1.397(3) . ?
C2 H2A 0.9500 . ?
N3 C13 1.338(3) . ?
N3 C17 1.343(3) . ?
N3 H3 0.8800 . ?
C3 C4 1.398(3) . ?
C3 C11 1.501(3) . ?
N4 C22 1.330(3) . ?
N4 C18 1.342(2) . ?
N4 H4 0.8800 . ?
C4 C5 1.373(3) . ?
C4 H4A 0.9500 . ?
Cl5 Bi1 2.9023(5) 2_675 ?
C5 H5 0.9500 . ?
C6 C7 1.370(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.399(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(3) . ?
C8 C12 1.500(3) . ?
C9 C10 1.370(3) . ?
C9 H9 0.9500 . ?
Cl10 Bi2 2.8986(5) 2_766 ?
C10 H10 0.9500 . ?
C11 C12 1.534(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.395(3) . ?
C15 C23 1.498(3) . ?
C16 C17 1.378(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.365(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.397(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(3) . ?
C20 C24 1.499(3) . ?
C21 C22 1.375(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.533(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
O1W H1WA 0.80(3) . ?
O1W H1WB 0.819(16) . ?
O2W H2WA 0.81(2) . ?
O2W H2WB 0.85(3) . ?

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
Cl2 Bi1 Cl3 87.948(16) . . ?
Cl2 Bi1 Cl4 87.330(16) . . ?
Cl3 Bi1 Cl4 93.007(16) . . ?
Cl2 Bi1 Cl1 91.401(16) . . ?
Cl3 Bi1 Cl1 92.165(16) . . ?
Cl4 Bi1 Cl1 174.626(13) . . ?
Cl2 Bi1 Cl5 94.409(15) . 2_675 ?
Cl3 Bi1 Cl5 177.641(14) . 2_675 ?
Cl4 Bi1 Cl5 87.022(15) . 2_675 ?
Cl1 Bi1 Cl5 87.870(15) . 2_675 ?
Cl2 Bi1 Cl5 171.306(15) . . ?
Cl3 Bi1 Cl5 86.792(15) . . ?
Cl4 Bi1 Cl5 86.039(15) . . ?
Cl1 Bi1 Cl5 95.710(14) . . ?
Cl5 Bi1 Cl5 90.857(13) 2_675 . ?
C5 N1 C1 121.67(18) . . ?
C5 N1 H1 119.2 . . ?
C1 N1 H1 119.2 . . ?
N1 C1 C2 119.61(18) . . ?
N1 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
Cl8 Bi2 Cl7 87.458(16) . . ?
Cl8 Bi2 Cl9 93.698(17) . . ?
Cl7 Bi2 Cl9 89.323(16) . . ?
Cl8 Bi2 Cl6 92.617(16) . . ?
Cl7 Bi2 Cl6 86.450(15) . . ?
Cl9 Bi2 Cl6 172.237(15) . . ?
Cl8 Bi2 Cl10 173.217(15) . . ?
Cl7 Bi2 Cl10 98.512(15) . . ?
Cl9 Bi2 Cl10 89.611(15) . . ?
Cl6 Bi2 Cl10 84.586(14) . . ?
Cl8 Bi2 Cl10 86.162(15) . 2_766 ?
Cl7 Bi2 Cl10 172.478(14) . 2_766 ?
Cl9 Bi2 Cl10 95.057(15) . 2_766 ?
Cl6 Bi2 Cl10 89.864(14) . 2_766 ?
Cl10 Bi2 Cl10 87.650(14) . 2_766 ?
C6 N2 C10 122.29(18) . . ?
C6 N2 H2 118.9 . . ?
C10 N2 H2 118.9 . . ?
C1 C2 C3 120.51(18) . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 H2A 119.7 . . ?
C13 N3 C17 122.30(18) . . ?
C13 N3 H3 118.8 . . ?
C17 N3 H3 118.8 . . ?
C2 C3 C4 117.72(18) . . ?
C2 C3 C11 121.14(17) . . ?
C4 C3 C11 121.13(18) . . ?
C22 N4 C18 122.73(18) . . ?
C22 N4 H4 118.6 . . ?
C18 N4 H4 118.6 . . ?
C5 C4 C3 119.96(18) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
Bi1 Cl5 Bi1 89.143(13) 2_675 . ?
N1 C5 C4 120.47(18) . . ?
N1 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N2 C6 C7 119.79(18) . . ?
N2 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 120.03(19) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 118.04(18) . . ?
C9 C8 C12 121.09(19) . . ?
C7 C8 C12 120.87(19) . . ?
C10 C9 C8 119.93(18) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
Bi2 Cl10 Bi2 92.349(14) . 2_766 ?
N2 C10 C9 119.86(19) . . ?
N2 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C3 C11 C12 111.46(16) . . ?
C3 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C3 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C8 C12 C11 112.71(17) . . ?
C8 C12 H12A 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C8 C12 H12B 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N3 C13 C14 119.80(18) . . ?
N3 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 120.16(18) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C16 117.98(18) . . ?
C14 C15 C23 120.88(17) . . ?
C16 C15 C23 121.14(17) . . ?
C17 C16 C15 120.09(18) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
N3 C17 C16 119.58(18) . . ?
N3 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
N4 C18 C19 119.88(19) . . ?
N4 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 119.74(19) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 118.14(19) . . ?
C21 C20 C24 121.1(2) . . ?
C19 C20 C24 120.7(2) . . ?
C22 C21 C20 120.02(19) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
N4 C22 C21 119.47(19) . . ?
N4 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C15 C23 C24 110.89(16) . . ?
C15 C23 H23A 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C15 C23 H23B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 108.0 . . ?
C20 C24 C23 112.82(17) . . ?
C20 C24 H24A 109.0 . . ?
C23 C24 H24A 109.0 . . ?
C20 C24 H24B 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?
H1WA O1W H1WB 107(2) . . ?
H2WA O2W H2WB 104(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1W 0.88 1.86 2.686(2) 155.1 .
N1 H1 Cl4 0.88 2.98 3.5239(17) 121.7 2_675
N2 H2 Cl2 0.88 2.69 3.3606(18) 133.9 1_566
N2 H2 Cl3 0.88 2.51 3.2194(18) 138.7 1_566
N3 H3 O2W 0.88 2.18 2.895(2) 137.6 .
N3 H3 Cl6 0.88 2.69 3.3248(17) 130.2 .
N4 H4 Cl7 0.88 2.62 3.3117(17) 135.7 2_755
N4 H4 Cl8 0.88 2.58 3.2656(18) 135.9 2_755
O1W H1WB O2W 0.819(16) 2.021(17) 2.829(2) 169(2) .
O1W H1WA Cl10 0.80(3) 2.68(3) 3.2788(17) 132(2) .
O2W H2WA Cl1 0.81(2) 2.52(2) 3.2587(16) 151(2) .
O2W H2WB Cl5 0.85(3) 2.33(3) 3.1702(16) 168(2) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.103
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1056758'
_audit_update_record             
;
2015-03-28 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H14 N2), Bi2 Br10, 2(H2 O)'
_chemical_formula_sum            'C24 H32 Bi2 Br10 N4 O2'
_chemical_formula_weight         1625.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9694(4)
_cell_length_b                   10.7558(5)
_cell_length_c                   10.8145(5)
_cell_angle_alpha                63.2080(10)
_cell_angle_beta                 68.5300(10)
_cell_angle_gamma                81.1380(10)
_cell_volume                     963.23(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4529
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      27.65

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.802
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    19.522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1270
_exptl_absorpt_correction_T_max  0.2456
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex DUO CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 25
_diffrn_reflns_number            9717
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         27.68
_reflns_number_total             4444
_reflns_number_gt                3805
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.0243P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4444
_refine_ls_number_parameters     199
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0491
_refine_ls_wR_factor_gt          0.0474
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.923432(15) 0.213237(14) 0.418631(14) 0.01661(5) Uani 1 1 d . . .
Br1 Br 0.79078(4) 0.15379(4) 0.25189(4) 0.02251(9) Uani 1 1 d . . .
N1 N 0.4993(4) 0.3999(3) 0.2478(4) 0.0250(8) Uani 1 1 d . . .
H1 H 0.5145 0.3125 0.3018 0.030 Uiso 1 1 calc R . .
C1 C 0.6105(4) 0.4790(4) 0.1332(4) 0.0241(9) Uani 1 1 d . . .
H1A H 0.7041 0.4406 0.1128 0.029 Uiso 1 1 calc R . .
Br2 Br 0.68449(4) 0.36838(4) 0.48741(4) 0.02460(10) Uani 1 1 d . . .
N2 N 0.1996(3) 1.3038(3) -0.1991(3) 0.0219(7) Uani 1 1 d . . .
H2 H 0.1791 1.3910 -0.2480 0.026 Uiso 1 1 calc R . .
C2 C 0.5882(4) 0.6140(4) 0.0467(4) 0.0230(9) Uani 1 1 d . . .
H2A H 0.6659 0.6687 -0.0357 0.028 Uiso 1 1 calc R . .
Br3 Br 1.05226(4) 0.44571(4) 0.17391(4) 0.02489(10) Uani 1 1 d . . .
C3 C 0.4504(4) 0.6730(4) 0.0787(4) 0.0185(8) Uani 1 1 d . . .
Br4 Br 1.03511(4) 0.25924(5) 0.59654(4) 0.02799(10) Uani 1 1 d . . .
C4 C 0.3408(4) 0.5875(4) 0.1983(4) 0.0268(10) Uani 1 1 d . . .
H4 H 0.2465 0.6233 0.2236 0.032 Uiso 1 1 calc R . .
Br5 Br 0.80151(4) -0.06164(4) 0.67600(4) 0.02360(10) Uani 1 1 d . . .
C5 C 0.3672(4) 0.4510(4) 0.2810(4) 0.0268(10) Uani 1 1 d . . .
H5 H 0.2909 0.3929 0.3622 0.032 Uiso 1 1 calc R . .
C6 C 0.3229(4) 1.2508(4) -0.2597(4) 0.0262(10) Uani 1 1 d . . .
H6 H 0.3869 1.3075 -0.3540 0.031 Uiso 1 1 calc R . .
C7 C 0.3565(4) 1.1157(4) -0.1867(4) 0.0244(9) Uani 1 1 d . . .
H7 H 0.4440 1.0785 -0.2300 0.029 Uiso 1 1 calc R . .
C8 C 0.2629(4) 1.0323(4) -0.0488(4) 0.0212(9) Uani 1 1 d . . .
C9 C 0.1354(4) 1.0927(4) 0.0100(4) 0.0240(9) Uani 1 1 d . . .
H9 H 0.0687 1.0386 0.1037 0.029 Uiso 1 1 calc R . .
C10 C 0.1071(4) 1.2281(4) -0.0664(4) 0.0235(9) Uani 1 1 d . . .
H10 H 0.0214 1.2689 -0.0254 0.028 Uiso 1 1 calc R . .
C11 C 0.4294(4) 0.8227(4) -0.0192(4) 0.0225(9) Uani 1 1 d . . .
H11A H 0.4362 0.8292 -0.1156 0.027 Uiso 1 1 calc R . .
H11B H 0.5087 0.8801 -0.0363 0.027 Uiso 1 1 calc R . .
C12 C 0.2873(4) 0.8826(4) 0.0426(4) 0.0253(10) Uani 1 1 d . . .
H12A H 0.2086 0.8258 0.0576 0.030 Uiso 1 1 calc R . .
H12B H 0.2798 0.8728 0.1405 0.030 Uiso 1 1 calc R . .
O1W O 0.4162(4) 0.1321(3) 0.4685(4) 0.0468(10) Uani 1 1 d D . .
H1WC H 0.400(7) 0.103(7) 0.410(6) 0.070 Uiso 0.67 1 d PD . .
H1WB H 0.486(5) 0.078(6) 0.496(7) 0.070 Uiso 0.67 1 d PD . .
H1WA H 0.339(4) 0.101(7) 0.550(4) 0.070 Uiso 0.67 1 d PD . .


_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 Br3 2.7279(4) . ?
Bi1 Br2 2.7585(4) . ?
Bi1 Br4 2.7897(5) . ?
Bi1 Br1 2.9077(4) . ?
Bi1 Br5 3.0294(4) . ?
Bi1 Br5 3.0493(4) 2_756 ?
N1 C5 1.332(5) . ?
N1 C1 1.350(5) . ?
N1 H1 0.8800 . ?
C1 C2 1.365(5) . ?
C1 H1A 0.9500 . ?
N2 C10 1.335(5) . ?
N2 C6 1.341(5) . ?
N2 H2 0.8800 . ?
C2 C3 1.411(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.384(5) . ?
C3 C11 1.509(5) . ?
C4 C5 1.376(6) . ?
C4 H4 0.9500 . ?
Br5 Bi1 3.0493(4) 2_756 ?
C5 H5 0.9500 . ?
C6 C7 1.362(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.402(6) . ?
C8 C12 1.500(5) . ?
C9 C10 1.357(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.511(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O1W H1WC 0.888(19) . ?
O1W H1WB 0.886(19) . ?
O1W H1WA 0.896(19) . ?

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
Br3 Bi1 Br2 89.530(13) . . ?
Br3 Bi1 Br4 93.721(14) . . ?
Br2 Bi1 Br4 90.388(14) . . ?
Br3 Bi1 Br1 89.980(13) . . ?
Br2 Bi1 Br1 88.013(13) . . ?
Br4 Bi1 Br1 175.957(11) . . ?
Br3 Bi1 Br5 174.307(13) . . ?
Br2 Bi1 Br5 95.842(12) . . ?
Br4 Bi1 Br5 88.139(13) . . ?
Br1 Bi1 Br5 88.330(12) . . ?
Br3 Bi1 Br5 86.270(12) . 2_756 ?
Br2 Bi1 Br5 175.779(11) . 2_756 ?
Br4 Bi1 Br5 89.475(13) . 2_756 ?
Br1 Bi1 Br5 92.393(13) . 2_756 ?
Br5 Bi1 Br5 88.370(11) . 2_756 ?
C5 N1 C1 121.6(3) . . ?
C5 N1 H1 119.2 . . ?
C1 N1 H1 119.2 . . ?
N1 C1 C2 119.9(4) . . ?
N1 C1 H1A 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C10 N2 C6 121.8(4) . . ?
C10 N2 H2 119.1 . . ?
C6 N2 H2 119.1 . . ?
C1 C2 C3 120.4(4) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C4 C3 C2 117.1(3) . . ?
C4 C3 C11 123.8(4) . . ?
C2 C3 C11 119.1(3) . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
Bi1 Br5 Bi1 91.630(11) . 2_756 ?
N1 C5 C4 120.3(4) . . ?
N1 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
N2 C6 C7 120.2(4) . . ?
N2 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C8 120.0(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 117.6(4) . . ?
C7 C8 C12 125.2(4) . . ?
C9 C8 C12 117.2(3) . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
N2 C10 C9 120.0(4) . . ?
N2 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C3 C11 C12 114.1(3) . . ?
C3 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C3 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C8 C12 C11 116.1(3) . . ?
C8 C12 H12A 108.3 . . ?
C11 C12 H12A 108.3 . . ?
C8 C12 H12B 108.3 . . ?
C11 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
H1WC O1W H1WB 104(2) . . ?
H1WC O1W H1WA 103(2) . . ?
H1WB O1W H1WA 104(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1W 0.88 2.03 2.788(4) 143.9 .
N1 H1 Br1 0.88 3.01 3.615(3) 127.3 .
N2 H2 Br2 0.88 2.78 3.492(3) 139.3 2_675
N2 H2 Br3 0.88 2.78 3.422(3) 131.3 2_675
O1W H1WB O1W 0.886(19) 2.24(5) 2.992(7) 142(6) 2_656
O1W H1WA Br1 0.896(19) 2.74(5) 3.444(3) 136(6) 2_656
O1W H1WC Br5 0.888(19) 2.67(4) 3.433(4) 145(5) 2_656

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.918
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.145
