# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_platon
_database_code_depnum_ccdc_archive 'CCDC 1060713'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Ammonia-BODIPY
_chemical_name_common            Amino-BODIPY
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H6 B Br F7 N3'
_chemical_formula_sum            'C15 H6 B Br F7 N3'
_chemical_formula_weight         451.95

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   6.2039(4)
_cell_length_b                   12.3689(10)
_cell_length_c                   42.218(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3239.6(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6466
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      24.19

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    2.618
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.253
_exptl_absorpt_correction_T_max  0.370
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_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            13931
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         27.91
_reflns_number_total             3860
_reflns_number_gt                2393
_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-2014 (Sheldrick 2014)'
_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)+(0.0509P)²+4.6959P] 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         3860
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.09286(7) 0.24993(3) 0.030690(9) 0.05125(16) Uani 1 1 d . . .
F22 F 0.3838(6) 0.6008(2) 0.16198(7) 0.0958(11) Uani 1 1 d . . .
F23 F 0.3991(7) 0.6010(3) 0.22558(8) 0.1224(15) Uani 1 1 d . . .
F24 F 0.5539(6) 0.4275(4) 0.25697(6) 0.1159(14) Uani 1 1 d . . .
F25 F 0.6966(8) 0.2532(3) 0.22407(7) 0.1253(16) Uani 1 1 d . . .
F26 F 0.6875(6) 0.2536(2) 0.16058(7) 0.0868(10) Uani 1 1 d . . .
F35 F 0.5902(4) 0.3325(2) 0.03574(6) 0.0719(8) Uani 1 1 d . . .
F36 F 0.3758(4) 0.4783(2) 0.03285(5) 0.0637(7) Uani 1 1 d . . .
N7 N 0.3338(4) 0.3590(2) 0.07744(6) 0.0313(6) Uani 1 1 d . . .
N8 N 0.6535(4) 0.4770(2) 0.07238(6) 0.0318(6) Uani 1 1 d . . .
N9 N 0.8533(5) 0.5517(3) 0.03020(7) 0.0442(8) Uani 1 1 d . . .
H9A H 0.7669 0.5248 0.0164 0.053 Uiso 1 1 calc R . .
H9B H 0.9622 0.5896 0.0242 0.053 Uiso 1 1 calc R . .
C43 C 0.6712(6) 0.4779(3) 0.10564(7) 0.0335(8) Uani 1 1 d . . .
C57 C 0.3495(6) 0.3685(3) 0.11019(8) 0.0338(8) Uani 1 1 d . . .
C67 C 0.8189(6) 0.5349(3) 0.06072(8) 0.0360(8) Uani 1 1 d . . .
C73 C 0.5384(6) 0.4289(3) 0.15921(8) 0.0394(8) Uani 1 1 d . . .
C77 C 0.0597(6) 0.2666(3) 0.09932(9) 0.0460(10) Uani 1 1 d . . .
H77 H -0.0631 0.2241 0.1014 0.055 Uiso 1 1 calc R . .
C83 C 0.8612(6) 0.5397(3) 0.11351(9) 0.0392(8) Uani 1 1 d . . .
H83 H 0.9130 0.5532 0.1338 0.047 Uiso 1 1 calc R . .
C97 C 0.5228(6) 0.4268(3) 0.12401(7) 0.0335(8) Uani 1 1 d . . .
C118 C 0.1799(6) 0.3127(3) 0.12375(9) 0.0445(9) Uani 1 1 d . . .
H118 H 0.1511 0.3069 0.1453 0.053 Uiso 1 1 calc R . .
C131 C 0.1586(6) 0.2965(3) 0.07162(8) 0.0365(8) Uani 1 1 d . . .
C132 C 0.6152(7) 0.3411(4) 0.17612(9) 0.0544(11) Uani 1 1 d . . .
C149 C 0.4663(8) 0.5154(3) 0.17678(9) 0.0556(11) Uani 1 1 d . . .
C158 C 0.9495(6) 0.5742(3) 0.08653(9) 0.0433(9) Uani 1 1 d . . .
H158 H 1.0733 0.6161 0.0847 0.052 Uiso 1 1 calc R . .
C162 C 0.4737(9) 0.5148(5) 0.20980(11) 0.0726(15) Uani 1 1 d . . .
C187 C 0.5484(9) 0.4277(5) 0.22499(10) 0.0715(15) Uani 1 1 d . . .
C202 C 0.6212(8) 0.3400(5) 0.20883(11) 0.0729(15) Uani 1 1 d . . .
B6 B 0.4871(6) 0.4107(3) 0.05317(9) 0.0355(9) 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
Br1 C131 1.867(3) . ?
F22 C149 1.330(5) . ?
F23 C162 1.339(6) . ?
F24 C187 1.351(5) . ?
F25 C202 1.336(6) . ?
F26 C132 1.342(5) . ?
F35 B6 1.373(5) . ?
F36 B6 1.383(5) . ?
N7 C131 1.356(4) . ?
N7 C57 1.391(4) . ?
N7 B6 1.538(5) . ?
N8 C67 1.345(4) . ?
N8 C43 1.409(4) . ?
N8 B6 1.548(5) . ?
N9 C67 1.322(4) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
C43 C97 1.359(5) . ?
C43 C83 1.444(5) . ?
C57 C118 1.382(5) . ?
C57 C97 1.420(5) . ?
C67 C158 1.442(5) . ?
C73 C149 1.376(5) . ?
C73 C132 1.384(5) . ?
C73 C97 1.490(5) . ?
C77 C131 1.371(5) . ?
C77 C118 1.394(5) . ?
C77 H77 0.9300 . ?
C83 C158 1.334(5) . ?
C83 H83 0.9300 . ?
C118 H118 0.9300 . ?
C132 C202 1.382(6) . ?
C149 C162 1.395(6) . ?
C158 H158 0.9300 . ?
C162 C187 1.337(8) . ?
C187 C202 1.359(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
C131 N7 C57 106.5(3) . . ?
C131 N7 B6 127.7(3) . . ?
C57 N7 B6 125.7(3) . . ?
C67 N8 C43 107.5(3) . . ?
C67 N8 B6 126.8(3) . . ?
C43 N8 B6 125.3(3) . . ?
C67 N9 H9A 120.0 . . ?
C67 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C97 C43 N8 120.8(3) . . ?
C97 C43 C83 131.9(3) . . ?
N8 C43 C83 107.3(3) . . ?
C118 C57 N7 108.5(3) . . ?
C118 C57 C97 131.3(3) . . ?
N7 C57 C97 120.3(3) . . ?
N9 C67 N8 124.3(3) . . ?
N9 C67 C158 126.3(3) . . ?
N8 C67 C158 109.4(3) . . ?
C149 C73 C132 116.4(4) . . ?
C149 C73 C97 122.0(3) . . ?
C132 C73 C97 121.5(3) . . ?
C131 C77 C118 106.4(3) . . ?
C131 C77 H77 126.8 . . ?
C118 C77 H77 126.8 . . ?
C158 C83 C43 107.9(3) . . ?
C158 C83 H83 126.0 . . ?
C43 C83 H83 126.0 . . ?
C43 C97 C57 121.0(3) . . ?
C43 C97 C73 121.1(3) . . ?
C57 C97 C73 117.9(3) . . ?
C57 C118 C77 107.7(3) . . ?
C57 C118 H118 126.1 . . ?
C77 C118 H118 126.1 . . ?
N7 C131 C77 111.0(3) . . ?
N7 C131 Br1 121.3(3) . . ?
C77 C131 Br1 127.5(3) . . ?
F26 C132 C202 118.1(4) . . ?
F26 C132 C73 119.7(3) . . ?
C202 C132 C73 122.2(4) . . ?
F22 C149 C73 119.3(4) . . ?
F22 C149 C162 119.1(4) . . ?
C73 C149 C162 121.6(4) . . ?
C83 C158 C67 107.9(3) . . ?
C83 C158 H158 126.1 . . ?
C67 C158 H158 126.1 . . ?
C187 C162 F23 121.5(5) . . ?
C187 C162 C149 119.6(5) . . ?
F23 C162 C149 118.8(5) . . ?
C162 C187 F24 119.3(5) . . ?
C162 C187 C202 121.2(4) . . ?
F24 C187 C202 119.5(5) . . ?
F25 C202 C187 121.1(5) . . ?
F25 C202 C132 119.9(5) . . ?
C187 C202 C132 119.0(5) . . ?
F35 B6 F36 109.0(3) . . ?
F35 B6 N7 110.6(3) . . ?
F36 B6 N7 110.8(3) . . ?
F35 B6 N8 110.1(3) . . ?
F36 B6 N8 109.7(3) . . ?
N7 B6 N8 106.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C67 N8 C43 C97 178.9(3) . . . . ?
B6 N8 C43 C97 -7.0(5) . . . . ?
C67 N8 C43 C83 -0.6(4) . . . . ?
B6 N8 C43 C83 173.4(3) . . . . ?
C131 N7 C57 C118 -1.1(4) . . . . ?
B6 N7 C57 C118 178.7(3) . . . . ?
C131 N7 C57 C97 177.9(3) . . . . ?
B6 N7 C57 C97 -2.3(5) . . . . ?
C43 N8 C67 N9 -179.8(3) . . . . ?
B6 N8 C67 N9 6.3(6) . . . . ?
C43 N8 C67 C158 0.4(4) . . . . ?
B6 N8 C67 C158 -173.4(3) . . . . ?
C97 C43 C83 C158 -178.9(4) . . . . ?
N8 C43 C83 C158 0.5(4) . . . . ?
N8 C43 C97 C57 1.9(5) . . . . ?
C83 C43 C97 C57 -178.7(4) . . . . ?
N8 C43 C97 C73 -179.0(3) . . . . ?
C83 C43 C97 C73 0.4(6) . . . . ?
C118 C57 C97 C43 -178.7(4) . . . . ?
N7 C57 C97 C43 2.6(5) . . . . ?
C118 C57 C97 C73 2.2(6) . . . . ?
N7 C57 C97 C73 -176.6(3) . . . . ?
C149 C73 C97 C43 81.5(5) . . . . ?
C132 C73 C97 C43 -102.3(4) . . . . ?
C149 C73 C97 C57 -99.4(4) . . . . ?
C132 C73 C97 C57 76.9(5) . . . . ?
N7 C57 C118 C77 1.0(4) . . . . ?
C97 C57 C118 C77 -177.8(4) . . . . ?
C131 C77 C118 C57 -0.5(4) . . . . ?
C57 N7 C131 C77 0.8(4) . . . . ?
B6 N7 C131 C77 -179.0(3) . . . . ?
C57 N7 C131 Br1 -173.2(2) . . . . ?
B6 N7 C131 Br1 7.0(5) . . . . ?
C118 C77 C131 N7 -0.2(4) . . . . ?
C118 C77 C131 Br1 173.4(3) . . . . ?
C149 C73 C132 F26 179.8(4) . . . . ?
C97 C73 C132 F26 3.3(6) . . . . ?
C149 C73 C132 C202 -0.4(7) . . . . ?
C97 C73 C132 C202 -176.9(4) . . . . ?
C132 C73 C149 F22 -177.8(4) . . . . ?
C97 C73 C149 F22 -1.3(6) . . . . ?
C132 C73 C149 C162 1.0(7) . . . . ?
C97 C73 C149 C162 177.4(4) . . . . ?
C43 C83 C158 C67 -0.3(4) . . . . ?
N9 C67 C158 C83 -179.9(4) . . . . ?
N8 C67 C158 C83 -0.1(4) . . . . ?
F22 C149 C162 C187 177.4(5) . . . . ?
C73 C149 C162 C187 -1.4(8) . . . . ?
F22 C149 C162 F23 -0.6(7) . . . . ?
C73 C149 C162 F23 -179.3(4) . . . . ?
F23 C162 C187 F24 -1.7(8) . . . . ?
C149 C162 C187 F24 -179.6(5) . . . . ?
F23 C162 C187 C202 179.1(5) . . . . ?
C149 C162 C187 C202 1.2(8) . . . . ?
C162 C187 C202 F25 179.7(5) . . . . ?
F24 C187 C202 F25 0.5(8) . . . . ?
C162 C187 C202 C132 -0.7(8) . . . . ?
F24 C187 C202 C132 -179.9(4) . . . . ?
F26 C132 C202 F25 -0.3(7) . . . . ?
C73 C132 C202 F25 179.9(4) . . . . ?
F26 C132 C202 C187 -179.9(5) . . . . ?
C73 C132 C202 C187 0.3(8) . . . . ?
C131 N7 B6 F35 -62.6(5) . . . . ?
C57 N7 B6 F35 117.7(4) . . . . ?
C131 N7 B6 F36 58.5(5) . . . . ?
C57 N7 B6 F36 -121.2(4) . . . . ?
C131 N7 B6 N8 177.8(3) . . . . ?
C57 N7 B6 N8 -1.9(5) . . . . ?
C67 N8 B6 F35 59.4(5) . . . . ?
C43 N8 B6 F35 -113.4(4) . . . . ?
C67 N8 B6 F36 -60.6(5) . . . . ?
C43 N8 B6 F36 126.6(3) . . . . ?
C67 N8 B6 N7 179.4(3) . . . . ?
C43 N8 B6 N7 6.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.91
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.080
_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       Luminescent
