# 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 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1493118'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;

_audit_creation_date             2016-05-15T22:58:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C15 H14 N4, Bi Br5, H2 O'
_chemical_formula_sum            'C15 H16 Bi Br5 N4 O'
_chemical_formula_weight         876.85

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.4372(6)
_cell_length_b                   19.3000(10)
_cell_length_c                   20.3261(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4486.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5813
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      26.98

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    2.596
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             3200

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    16.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.2654
_exptl_absorpt_correction_T_max  0.7457

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.054
_diffrn_reflns_number            53376
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         28.343
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             5588
_reflns_number_gt                4138
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5588
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0895
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.346
_refine_diff_density_min         -1.608
_refine_diff_density_rms         0.25

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.06505(2) 0.00853(2) 0.74288(2) 0.01472(8) Uani 1 1 d . . . . .
Br1 Br -0.17244(5) 0.00612(4) 0.72382(4) 0.03063(18) Uani 1 1 d . . . . .
Br2 Br 0.08927(5) -0.09124(3) 0.63926(3) 0.02292(15) Uani 1 1 d . . . . .
Br3 Br 0.07013(6) 0.11820(3) 0.64790(3) 0.02800(17) Uani 1 1 d . . . . .
Br4 Br 0.04455(6) -0.10087(3) 0.83142(4) 0.02619(16) Uani 1 1 d . . . . .
Br5 Br 0.04790(6) 0.10213(3) 0.84878(3) 0.02451(15) Uani 1 1 d . . . . .
O1 O -0.1006(5) 0.2162(3) 0.5438(3) 0.0572(17) Uani 1 1 d . . . . .
H1 H -0.0847 0.2319 0.5049 0.069 Uiso 1 1 d R U . . .
H2 H -0.058 0.1932 0.567 0.069 Uiso 1 1 d R U . . .
N1 N 0.1972(4) 0.2362(3) 0.3236(3) 0.0198(12) Uani 1 1 d . . . . .
N2 N 0.2009(4) 0.0608(3) 0.4945(3) 0.0198(12) Uani 1 1 d . . . . .
N3 N 0.3511(5) 0.2775(3) 0.0806(3) 0.0279(13) Uani 1 1 d . . . . .
N4 N 0.3851(5) -0.1884(3) 0.5341(3) 0.0337(15) Uani 1 1 d . . . . .
C1 C 0.2854(6) 0.2797(3) 0.3139(4) 0.0277(16) Uani 1 1 d . . . . .
H1A H 0.3191 0.3029 0.3505 0.033 Uiso 1 1 calc R U . . .
C2 C 0.3287(6) 0.2919(3) 0.2521(3) 0.0267(16) Uani 1 1 d . . . . .
H2A H 0.3917 0.3232 0.2457 0.032 Uiso 1 1 calc R U . . .
C3 C 0.2797(5) 0.2580(3) 0.2000(3) 0.0196(14) Uani 1 1 d . . . . .
C4 C 0.1891(6) 0.2111(3) 0.2104(3) 0.0274(16) Uani 1 1 d . . . . .
H4A H 0.1564 0.186 0.1746 0.033 Uiso 1 1 calc R U . . .
C5 C 0.1479(6) 0.2016(3) 0.2726(3) 0.0248(15) Uani 1 1 d . . . . .
H5A H 0.0847 0.1707 0.2803 0.03 Uiso 1 1 calc R U . . .
C6 C 0.1528(5) 0.2218(3) 0.3910(3) 0.0213(14) Uani 1 1 d . . . . .
H6A H 0.0665 0.218 0.3904 0.026 Uiso 1 1 calc R U . . .
H6B H 0.1748 0.2599 0.4211 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2062(5) 0.1544(3) 0.4143(3) 0.0195(14) Uani 1 1 d . . . . .
H7A H 0.1938 0.1183 0.3805 0.023 Uiso 1 1 calc R U . . .
H7B H 0.2915 0.1606 0.42 0.023 Uiso 1 1 calc R U . . .
C8 C 0.1532(5) 0.1310(3) 0.4783(3) 0.0193(14) Uani 1 1 d . . . . .
H8A H 0.1731 0.1642 0.5137 0.023 Uiso 1 1 calc R U . . .
H8B H 0.0671 0.1289 0.4743 0.023 Uiso 1 1 calc R U . . .
C9 C 0.2904(5) 0.0544(3) 0.5367(3) 0.0244(15) Uani 1 1 d . . . . .
H9A H 0.3187 0.094 0.5594 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3418(6) -0.0094(3) 0.5474(3) 0.0248(15) Uani 1 1 d . . . . .
H10A H 0.4065 -0.0139 0.5764 0.03 Uiso 1 1 calc R U . . .
C11 C 0.2970(5) -0.0668(3) 0.5148(3) 0.0211(14) Uani 1 1 d . . . . .
C12 C 0.2029(5) -0.0594(3) 0.4725(3) 0.0223(14) Uani 1 1 d . . . . .
H12A H 0.1717 -0.0985 0.4502 0.027 Uiso 1 1 calc R U . . .
C13 C 0.1551(6) 0.0054(3) 0.4632(3) 0.0238(15) Uani 1 1 d . . . . .
H13A H 0.0899 0.011 0.4347 0.029 Uiso 1 1 calc R U . . .
C14 C 0.3203(5) 0.2691(3) 0.1329(4) 0.0224(15) Uani 1 1 d . . . . .
C15 C 0.3471(6) -0.1343(4) 0.5254(3) 0.0252(15) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 2.7442(7) . ?
Bi1 Br4 2.7841(7) . ?
Bi1 Br5 2.8170(7) . ?
Bi1 Br3 2.8654(7) . ?
Bi1 Br2 2.8672(7) . ?
Bi1 Br1 3.0780(7) 6_657 ?
Br1 Bi1 3.0780(7) 6_557 ?
O1 H1 0.8681 . ?
O1 H2 0.8102 . ?
N1 C1 1.327(8) . ?
N1 C5 1.355(8) . ?
N1 C6 1.487(8) . ?
N2 C9 1.341(8) . ?
N2 C13 1.351(8) . ?
N2 C8 1.497(7) . ?
N3 C14 1.132(8) . ?
N4 C15 1.145(8) . ?
C1 C2 1.370(9) . ?
C1 H1A 0.95 . ?
C2 C3 1.366(9) . ?
C2 H2A 0.95 . ?
C3 C4 1.392(8) . ?
C3 C14 1.456(9) . ?
C4 C5 1.362(9) . ?
C4 H4A 0.95 . ?
C5 H5A 0.95 . ?
C6 C7 1.512(8) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.505(8) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 C10 1.381(8) . ?
C9 H9A 0.95 . ?
C10 C11 1.388(8) . ?
C10 H10A 0.95 . ?
C11 C12 1.385(9) . ?
C11 C15 1.439(8) . ?
C12 C13 1.377(8) . ?
C12 H12A 0.95 . ?
C13 H13A 0.95 . ?

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 Br4 89.71(2) . . ?
Br1 Bi1 Br5 92.85(2) . . ?
Br4 Bi1 Br5 89.23(2) . . ?
Br1 Bi1 Br3 86.41(2) . . ?
Br4 Bi1 Br3 175.86(2) . . ?
Br5 Bi1 Br3 92.44(2) . . ?
Br1 Bi1 Br2 88.89(2) . . ?
Br4 Bi1 Br2 88.49(2) . . ?
Br5 Bi1 Br2 177.13(2) . . ?
Br3 Bi1 Br2 89.95(2) . . ?
Br1 Bi1 Br1 175.059(15) . 6_657 ?
Br4 Bi1 Br1 85.90(2) . 6_657 ?
Br5 Bi1 Br1 84.81(2) . 6_657 ?
Br3 Bi1 Br1 98.02(2) . 6_657 ?
Br2 Bi1 Br1 93.28(2) . 6_657 ?
Bi1 Br1 Bi1 159.10(3) . 6_557 ?
H1 O1 H2 126.7 . . ?
C1 N1 C5 120.9(6) . . ?
C1 N1 C6 121.0(6) . . ?
C5 N1 C6 118.0(5) . . ?
C9 N2 C13 121.6(6) . . ?
C9 N2 C8 120.2(5) . . ?
C13 N2 C8 118.2(5) . . ?
N1 C1 C2 121.3(6) . . ?
N1 C1 H1A 119.3 . . ?
C2 C1 H1A 119.3 . . ?
C3 C2 C1 118.7(6) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 119.9(6) . . ?
C2 C3 C14 121.7(6) . . ?
C4 C3 C14 118.4(6) . . ?
C5 C4 C3 119.1(6) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
N1 C5 C4 120.0(6) . . ?
N1 C5 H5A 120 . . ?
C4 C5 H5A 120 . . ?
N1 C6 C7 108.1(5) . . ?
N1 C6 H6A 110.1 . . ?
C7 C6 H6A 110.1 . . ?
N1 C6 H6B 110.1 . . ?
C7 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C8 C7 C6 111.5(5) . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108 . . ?
N2 C8 C7 108.4(5) . . ?
N2 C8 H8A 110 . . ?
C7 C8 H8A 110 . . ?
N2 C8 H8B 110 . . ?
C7 C8 H8B 110 . . ?
H8A C8 H8B 108.4 . . ?
N2 C9 C10 120.5(6) . . ?
N2 C9 H9A 119.7 . . ?
C10 C9 H9A 119.7 . . ?
C9 C10 C11 118.6(6) . . ?
C9 C10 H10A 120.7 . . ?
C11 C10 H10A 120.7 . . ?
C12 C11 C10 120.0(6) . . ?
C12 C11 C15 119.7(6) . . ?
C10 C11 C15 120.3(6) . . ?
C13 C12 C11 119.2(6) . . ?
C13 C12 H12A 120.4 . . ?
C11 C12 H12A 120.4 . . ?
N2 C13 C12 120.0(6) . . ?
N2 C13 H13A 120 . . ?
C12 C13 H13A 120 . . ?
N3 C14 C3 179.4(8) . . ?
N4 C15 C11 178.8(8) . . ?

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
O1 H1 N3 0.87 2.08 2.847(8) 146.7 6_556
O1 H2 Br3 0.81 2.64 3.444(5) 176.5 .
C1 H1A O1 0.95 2.36 3.174(9) 142.7 4_556
C2 H2A Br5 0.95 2.99 3.831(7) 148 4_556
C4 H4A Br4 0.95 2.83 3.520(7) 130.4 5_556
C5 H5A Br2 0.95 3 3.886(7) 156.3 5_556
C5 H5A Br4 0.95 3.03 3.619(6) 121.9 5_556
C6 H6A Br2 0.99 3.09 3.793(6) 129.5 5_556
C6 H6B N4 0.99 2.6 3.414(9) 139.9 8_665
C7 H7B Br4 0.99 2.84 3.469(6) 121.7 2_554
C8 H8A Br3 0.99 3.1 3.585(6) 111.5 .
C8 H8A N3 0.99 2.69 3.543(8) 144.1 7_566
C8 H8B Br2 0.99 3.01 3.740(6) 131.7 5_556
C9 H9A N3 0.95 2.54 3.436(9) 156.4 7_566
C10 H10A Br4 0.95 2.97 3.816(7) 149 6_657
C12 H12A O1 0.95 2.41 3.261(8) 148.2 5_556
C13 H13A Br2 0.95 2.98 3.859(7) 155.2 5_556

