# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_TRY1
_database_code_depnum_ccdc_archive 'CCDC 1454983'
_audit_update_record             
;
2016-02-22 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        'Zwitterionic Oxo-BODIPY'
_chemical_name_common            Oxo-BODIPY
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 B F7 N3 O'
_chemical_formula_sum            'C18 H13 B F7 N3 O'
_chemical_formula_weight         431.12

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'
B B 0.0013 0.0007 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.2794(4)
_cell_length_b                   9.0171(2)
_cell_length_c                   13.5025(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.8910(10)
_cell_angle_gamma                90
_cell_volume                     1726.18(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      32.59

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12005
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.436
_diffrn_reflns_theta_max         32.908
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6299
_reflns_number_gt                5298
_reflns_threshold_expression     'I > 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       '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          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²+0.7175P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6299
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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_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
F3 F 0.25353(5) 1.10284(7) 0.40043(5) 0.02220(14) Uani 1 1 d . . . . .
F2 F 0.41648(4) 0.99342(9) 0.03169(5) 0.02345(15) Uani 1 1 d . . . . .
F1 F 0.35177(5) 0.77023(8) 0.04698(5) 0.02350(14) Uani 1 1 d . . . . .
F4 F 0.13372(5) 1.04299(9) 0.49904(6) 0.02792(16) Uani 1 1 d . . . . .
N2 N 0.41370(5) 0.92091(8) 0.20546(6) 0.01148(13) Uani 1 1 d . . . . .
N1 N 0.26831(6) 0.99473(9) 0.05257(6) 0.01333(14) Uani 1 1 d . . . . .
O1 O 0.22785(6) 1.05954(10) -0.12673(6) 0.02156(16) Uani 1 1 d . . . . .
F7 F 0.13298(5) 0.69338(8) 0.17184(6) 0.02668(16) Uani 1 1 d . . . . .
F6 F 0.01254(6) 0.63663(9) 0.26995(6) 0.03053(17) Uani 1 1 d . . . . .
C10 C 0.19764(6) 0.90080(10) 0.28244(7) 0.01327(16) Uani 1 1 d . . . . .
N3 N 0.58702(6) 0.89980(9) 0.24202(6) 0.01252(14) Uani 1 1 d . . . . .
F5 F 0.01314(5) 0.80978(9) 0.43503(6) 0.02974(17) Uani 1 1 d . . . . .
C6 C 0.50962(7) 0.88088(10) 0.37837(7) 0.01400(16) Uani 1 1 d . . . . .
H3 H 0.5648 0.8664 0.4404 0.017 Uiso 1 1 calc R U . . .
C9 C 0.25802(6) 0.93471(10) 0.22106(7) 0.01257(15) Uani 1 1 d . . . . .
C8 C 0.35874(6) 0.91234(10) 0.26795(7) 0.01159(15) Uani 1 1 d . . . . .
C5 C 0.50542(6) 0.89872(10) 0.27517(7) 0.01208(15) Uani 1 1 d . . . . .
C13 C 0.07342(7) 0.83747(13) 0.38704(8) 0.01956(19) Uani 1 1 d . . . . .
C7 C 0.41606(7) 0.88843(10) 0.37372(7) 0.01356(16) Uani 1 1 d . . . . .
H4 H 0.3960 0.8789 0.4321 0.016 Uiso 1 1 calc R U . . .
C16 C 0.60258(7) 1.05392(10) 0.20709(8) 0.01646(17) Uani 1 1 d . . . . .
H6 H 0.5467 1.0848 0.1461 0.025 Uiso 1 1 calc R U . . .
H7 H 0.6576 1.0531 0.1863 0.025 Uiso 1 1 calc R U . . .
H5 H 0.6136 1.1236 0.2662 0.025 Uiso 1 1 calc R U . . .
C1 C 0.21705(6) 0.98188(10) 0.11823(7) 0.01332(16) Uani 1 1 d . . . . .
C15 C 0.13522(7) 0.78124(11) 0.25256(8) 0.01703(17) Uani 1 1 d . . . . .
C12 C 0.13524(7) 0.95566(12) 0.41980(8) 0.01755(18) Uani 1 1 d . . . . .
C2 C 0.12184(7) 1.03447(12) 0.06026(8) 0.01789(18) Uani 1 1 d . . . . .
H1 H 0.0722 1.0382 0.0865 0.021 Uiso 1 1 calc R U . . .
C4 C 0.20847(7) 1.04597(11) -0.04698(8) 0.01593(17) Uani 1 1 d . . . . .
C11 C 0.19603(7) 0.98536(11) 0.36770(8) 0.01488(16) Uani 1 1 d . . . . .
C17 C 0.57709(7) 0.78850(11) 0.15474(8) 0.01742(17) Uani 1 1 d . . . . .
H10 H 0.5667 0.6895 0.1782 0.026 Uiso 1 1 calc R U . . .
H8 H 0.6348 0.7880 0.1392 0.026 Uiso 1 1 calc R U . . .
H9 H 0.5234 0.8158 0.0902 0.026 Uiso 1 1 calc R U . . .
C14 C 0.07352(7) 0.74985(12) 0.30307(8) 0.01971(19) Uani 1 1 d . . . . .
C18 C 0.67503(7) 0.85963(14) 0.33515(9) 0.0222(2) Uani 1 1 d . . . . .
H13 H 0.6852 0.9313 0.3929 0.033 Uiso 1 1 calc R U . . .
H11 H 0.7292 0.8613 0.3128 0.033 Uiso 1 1 calc R U . . .
H12 H 0.6682 0.7600 0.3604 0.033 Uiso 1 1 calc R U . . .
B1 B 0.36385(7) 0.91916(12) 0.07980(8) 0.01419(18) Uani 1 1 d . . . . .
C3 C 0.11646(7) 1.07697(13) -0.03744(9) 0.02006(19) Uani 1 1 d . . . . .
H2 H 0.0628 1.1196 -0.0912 0.024 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
F3 C11 1.3415(11) . ?
F2 B1 1.3808(12) . ?
F1 B1 1.4046(13) . ?
F4 C12 1.3356(11) . ?
N2 C5 1.3807(12) . ?
N2 C8 1.3970(11) . ?
N2 B1 1.5797(13) . ?
N1 C1 1.3895(11) . ?
N1 C4 1.3928(12) . ?
N1 B1 1.5264(13) . ?
O1 C4 1.2247(12) . ?
F7 C15 1.3375(11) . ?
F6 C14 1.3414(12) . ?
C10 C11 1.3887(13) . ?
C10 C15 1.3956(13) . ?
C10 C9 1.4838(12) . ?
N3 C5 1.4735(11) . ?
N3 C18 1.5033(13) . ?
N3 C17 1.5119(12) . ?
N3 C16 1.5145(12) . ?
F5 C13 1.3325(11) . ?
C6 C5 1.3803(12) . ?
C6 C7 1.4091(13) . ?
C9 C1 1.3611(13) . ?
C9 C8 1.4434(13) . ?
C8 C7 1.3858(13) . ?
C13 C12 1.3828(15) . ?
C13 C14 1.3824(15) . ?
C1 C2 1.4508(13) . ?
C15 C14 1.3833(14) . ?
C12 C11 1.3844(13) . ?
C2 C3 1.3464(14) . ?
C4 C3 1.4854(14) . ?

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
C5 N2 C8 105.43(7) . . ?
C5 N2 B1 133.73(7) . . ?
C8 N2 B1 119.37(7) . . ?
C1 N1 C4 108.66(8) . . ?
C1 N1 B1 121.67(8) . . ?
C4 N1 B1 127.25(8) . . ?
C11 C10 C15 116.26(8) . . ?
C11 C10 C9 123.83(8) . . ?
C15 C10 C9 119.86(8) . . ?
C5 N3 C18 109.79(7) . . ?
C5 N3 C17 112.46(7) . . ?
C18 N3 C17 106.89(8) . . ?
C5 N3 C16 110.46(7) . . ?
C18 N3 C16 106.63(8) . . ?
C17 N3 C16 110.37(7) . . ?
C5 C6 C7 106.55(8) . . ?
C1 C9 C8 120.06(8) . . ?
C1 C9 C10 119.27(8) . . ?
C8 C9 C10 120.63(8) . . ?
C7 C8 N2 109.87(8) . . ?
C7 C8 C9 129.39(8) . . ?
N2 C8 C9 120.67(8) . . ?
C6 C5 N2 111.01(8) . . ?
C6 C5 N3 125.55(8) . . ?
N2 C5 N3 123.41(8) . . ?
F5 C13 C12 120.16(10) . . ?
F5 C13 C14 120.27(9) . . ?
C12 C13 C14 119.56(9) . . ?
C8 C7 C6 107.11(8) . . ?
C9 C1 N1 121.51(8) . . ?
C9 C1 C2 129.78(8) . . ?
N1 C1 C2 108.60(8) . . ?
F7 C15 C14 117.74(9) . . ?
F7 C15 C10 120.01(8) . . ?
C14 C15 C10 122.24(9) . . ?
F4 C12 C13 119.79(9) . . ?
F4 C12 C11 120.56(9) . . ?
C13 C12 C11 119.62(9) . . ?
C3 C2 C1 107.71(8) . . ?
O1 C4 N1 126.49(9) . . ?
O1 C4 C3 127.19(9) . . ?
N1 C4 C3 106.30(8) . . ?
F3 C11 C12 117.80(8) . . ?
F3 C11 C10 119.66(8) . . ?
C12 C11 C10 122.52(9) . . ?
F6 C14 C15 120.51(10) . . ?
F6 C14 C13 119.69(9) . . ?
C15 C14 C13 119.79(9) . . ?
F2 B1 F1 110.26(8) . . ?
F2 B1 N1 110.03(8) . . ?
F1 B1 N1 110.45(8) . . ?
F2 B1 N2 111.61(8) . . ?
F1 B1 N2 107.60(8) . . ?
N1 B1 N2 106.81(7) . . ?
C2 C3 C4 108.51(9) . . ?

_refine_diff_density_max         0.518
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.057

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 'Vapour Deposition'
####################################################################### 
# 
# 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_TRY1_a
_database_code_depnum_ccdc_archive 'CCDC 1454984'
_audit_update_record             
;
2016-02-22 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        'Zwitterionic Imino-BODIPY'
_chemical_name_common            Imino-BODIPY
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 B F7 N4'
_chemical_formula_sum            'C19 H16 B F7 N4'
_chemical_formula_weight         444.17

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'
B B 0.0013 0.0007 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.712(5)
_cell_length_b                   9.184(3)
_cell_length_c                   13.544(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.297(8)
_cell_angle_gamma                90
_cell_volume                     1820.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3242
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      26.11

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8660
_diffrn_reflns_av_unetI/netI     0.2191
_diffrn_reflns_av_R_equivalents  0.1585
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.618
_diffrn_reflns_theta_max         28.594
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4510
_reflns_number_gt                1646
_reflns_threshold_expression     'I > 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       '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          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0703P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4510
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2394
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1699
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_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_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
F2 F 0.40899(12) 0.5072(3) 0.53604(14) 0.0695(7) Uani 1 1 d . . . . .
F7 F 0.26534(15) 0.5897(3) 0.91320(16) 0.0712(7) Uani 1 1 d . . . . .
F1 F 0.34559(14) 0.2871(3) 0.53990(16) 0.0738(7) Uani 1 1 d . . . . .
F3 F 0.13361(17) 0.2058(3) 0.67870(18) 0.0837(8) Uani 1 1 d . . . . .
N2 N 0.40736(17) 0.4195(3) 0.70365(18) 0.0345(7) Uani 1 1 d . . . . .
N1 N 0.26508(16) 0.4998(3) 0.55737(19) 0.0392(7) Uani 1 1 d . . . . .
N4 N 0.57465(17) 0.3925(3) 0.73447(19) 0.0394(7) Uani 1 1 d . . . . .
F4 F 0.02395(16) 0.1480(3) 0.78388(18) 0.0911(8) Uani 1 1 d . . . . .
F6 F 0.15288(17) 0.5325(3) 1.01661(18) 0.1004(9) Uani 1 1 d . . . . .
F5 F 0.03099(15) 0.3118(3) 0.95245(18) 0.0956(9) Uani 1 1 d . . . . .
N3 N 0.22714(18) 0.5728(3) 0.3803(2) 0.0504(8) Uani 1 1 d . . . . .
C8 C 0.3562(2) 0.4105(3) 0.7693(2) 0.0360(8) Uani 1 1 d . . . . .
C5 C 0.4963(2) 0.3941(4) 0.7701(2) 0.0363(8) Uani 1 1 d . . . . .
C9 C 0.2586(2) 0.4355(3) 0.7259(2) 0.0377(8) Uani 1 1 d . . . . .
C10 C 0.2028(2) 0.4027(4) 0.7908(2) 0.0413(9) Uani 1 1 d . . . . .
C1 C 0.2181(2) 0.4855(4) 0.6261(2) 0.0367(8) Uani 1 1 d . . . . .
C4 C 0.2051(2) 0.5563(4) 0.4603(3) 0.0440(9) Uani 1 1 d . . . . .
C7 C 0.4138(2) 0.3838(4) 0.8716(2) 0.0410(9) Uani 1 1 d . . . . .
H4 H 0.3966 0.3738 0.9301 0.049 Uiso 1 1 calc R U . . .
C2 C 0.1269(2) 0.5370(4) 0.5720(3) 0.0506(10) Uani 1 1 d . . . . .
H1 H 0.0807 0.5383 0.5996 0.061 Uiso 1 1 calc R U . . .
C6 C 0.5019(2) 0.3746(4) 0.8721(2) 0.0452(9) Uani 1 1 d . . . . .
H3 H 0.5548 0.3582 0.9308 0.054 Uiso 1 1 calc R U . . .
C17 C 0.5612(2) 0.2882(4) 0.6440(3) 0.0547(10) Uani 1 1 d . . . . .
H8 H 0.5498 0.1923 0.6645 0.082 Uiso 1 1 calc R U . . .
H10 H 0.6151 0.2869 0.6265 0.082 Uiso 1 1 calc R U . . .
H9 H 0.5100 0.3192 0.5834 0.082 Uiso 1 1 calc R U . . .
C15 C 0.2062(2) 0.4786(4) 0.8786(3) 0.0497(10) Uani 1 1 d . . . . .
C12 C 0.0841(3) 0.2587(5) 0.8167(3) 0.0587(11) Uani 1 1 d . . . . .
C14 C 0.1489(3) 0.4495(5) 0.9331(3) 0.0565(11) Uani 1 1 d . . . . .
C13 C 0.0890(3) 0.3395(5) 0.9021(3) 0.0608(11) Uani 1 1 d . . . . .
C11 C 0.1410(3) 0.2893(4) 0.7628(3) 0.0532(10) Uani 1 1 d . . . . .
C3 C 0.1191(2) 0.5825(4) 0.4763(3) 0.0577(11) Uani 1 1 d . . . . .
H2 H 0.0672 0.6245 0.4270 0.069 Uiso 1 1 calc R U . . .
C16 C 0.5960(2) 0.5419(4) 0.7046(3) 0.0553(10) Uani 1 1 d . . . . .
H5 H 0.5439 0.5791 0.6477 0.083 Uiso 1 1 calc R U . . .
H7 H 0.6473 0.5365 0.6823 0.083 Uiso 1 1 calc R U . . .
H6 H 0.6103 0.6055 0.7647 0.083 Uiso 1 1 calc R U . . .
B1 B 0.3565(3) 0.4294(5) 0.5796(3) 0.0418(10) Uani 1 1 d . . . . .
C18 C 0.6578(2) 0.3432(5) 0.8235(3) 0.0723(13) Uani 1 1 d . . . . .
H12 H 0.6727 0.4127 0.8802 0.108 Uiso 1 1 calc R U . . .
H11 H 0.7079 0.3351 0.7992 0.108 Uiso 1 1 calc R U . . .
H13 H 0.6463 0.2501 0.8484 0.108 Uiso 1 1 calc R U . . .
C19 C 0.1547(3) 0.6342(7) 0.2843(3) 0.1050(18) Uani 1 1 d . . . . .
H16 H 0.0976 0.6366 0.2952 0.158 Uiso 1 1 calc R U . . .
H15 H 0.1485 0.5742 0.2240 0.158 Uiso 1 1 calc R U . . .
H14 H 0.1712 0.7312 0.2718 0.158 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
F2 B1 1.375(4) . ?
F7 C15 1.345(4) . ?
F1 B1 1.400(5) . ?
F3 C11 1.343(4) . ?
N2 C5 1.380(4) . ?
N2 C8 1.401(4) . ?
N2 B1 1.580(4) . ?
N1 C1 1.388(4) . ?
N1 C4 1.409(4) . ?
N1 B1 1.503(5) . ?
N4 C5 1.477(4) . ?
N4 C18 1.490(4) . ?
N4 C16 1.502(4) . ?
N4 C17 1.509(4) . ?
F4 C12 1.348(4) . ?
F6 C14 1.346(4) . ?
F5 C13 1.347(4) . ?
N3 C4 1.261(4) . ?
N3 C19 1.494(5) . ?
C8 C7 1.374(4) . ?
C8 C9 1.448(4) . ?
C5 C6 1.364(4) . ?
C9 C1 1.349(4) . ?
C9 C10 1.480(4) . ?
C10 C15 1.363(5) . ?
C10 C11 1.379(5) . ?
C1 C2 1.432(4) . ?
C4 C3 1.463(4) . ?
C7 C6 1.385(4) . ?
C7 H4 0.9300 . ?
C2 C3 1.325(4) . ?
C2 H1 0.9300 . ?
C6 H3 0.9300 . ?
C17 H8 0.9600 . ?
C17 H10 0.9600 . ?
C17 H9 0.9600 . ?
C15 C14 1.382(5) . ?
C12 C13 1.352(5) . ?
C12 C11 1.374(5) . ?
C14 C13 1.340(5) . ?
C3 H2 0.9300 . ?
C16 H5 0.9600 . ?
C16 H7 0.9600 . ?
C16 H6 0.9600 . ?
C18 H12 0.9600 . ?
C18 H11 0.9600 . ?
C18 H13 0.9600 . ?
C19 H16 0.9600 . ?
C19 H15 0.9600 . ?
C19 H14 0.9600 . ?

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
C5 N2 C8 104.7(2) . . ?
C5 N2 B1 134.8(2) . . ?
C8 N2 B1 119.6(2) . . ?
C1 N1 C4 108.8(3) . . ?
C1 N1 B1 121.9(3) . . ?
C4 N1 B1 127.7(3) . . ?
C5 N4 C18 109.2(2) . . ?
C5 N4 C16 111.9(3) . . ?
C18 N4 C16 106.2(3) . . ?
C5 N4 C17 112.6(3) . . ?
C18 N4 C17 106.7(3) . . ?
C16 N4 C17 109.9(2) . . ?
C4 N3 C19 115.7(3) . . ?
C7 C8 N2 109.4(3) . . ?
C7 C8 C9 130.5(3) . . ?
N2 C8 C9 120.0(3) . . ?
C6 C5 N2 111.2(3) . . ?
C6 C5 N4 125.1(3) . . ?
N2 C5 N4 123.7(2) . . ?
C1 C9 C8 120.3(3) . . ?
C1 C9 C10 120.0(3) . . ?
C8 C9 C10 119.7(3) . . ?
C15 C10 C11 115.3(3) . . ?
C15 C10 C9 124.7(3) . . ?
C11 C10 C9 120.0(3) . . ?
C9 C1 N1 122.2(3) . . ?
C9 C1 C2 130.2(3) . . ?
N1 C1 C2 107.6(3) . . ?
N3 C4 N1 123.2(3) . . ?
N3 C4 C3 131.5(3) . . ?
N1 C4 C3 105.3(3) . . ?
C8 C7 C6 107.9(3) . . ?
C8 C7 H4 126.1 . . ?
C6 C7 H4 126.1 . . ?
C3 C2 C1 108.9(3) . . ?
C3 C2 H1 125.5 . . ?
C1 C2 H1 125.5 . . ?
C5 C6 C7 106.8(3) . . ?
C5 C6 H3 126.6 . . ?
C7 C6 H3 126.6 . . ?
N4 C17 H8 109.5 . . ?
N4 C17 H10 109.5 . . ?
H8 C17 H10 109.5 . . ?
N4 C17 H9 109.5 . . ?
H8 C17 H9 109.5 . . ?
H10 C17 H9 109.5 . . ?
F7 C15 C10 119.7(3) . . ?
F7 C15 C14 117.5(3) . . ?
C10 C15 C14 122.7(4) . . ?
F4 C12 C13 120.8(4) . . ?
F4 C12 C11 119.5(4) . . ?
C13 C12 C11 119.7(4) . . ?
C13 C14 F6 120.2(3) . . ?
C13 C14 C15 119.8(4) . . ?
F6 C14 C15 119.9(4) . . ?
C14 C13 F5 120.7(4) . . ?
C14 C13 C12 119.9(3) . . ?
F5 C13 C12 119.3(4) . . ?
F3 C11 C12 117.5(3) . . ?
F3 C11 C10 120.0(3) . . ?
C12 C11 C10 122.5(3) . . ?
C2 C3 C4 109.3(3) . . ?
C2 C3 H2 125.4 . . ?
C4 C3 H2 125.4 . . ?
N4 C16 H5 109.5 . . ?
N4 C16 H7 109.5 . . ?
H5 C16 H7 109.5 . . ?
N4 C16 H6 109.5 . . ?
H5 C16 H6 109.5 . . ?
H7 C16 H6 109.5 . . ?
F2 B1 F1 109.3(3) . . ?
F2 B1 N1 111.7(3) . . ?
F1 B1 N1 110.4(3) . . ?
F2 B1 N2 109.6(3) . . ?
F1 B1 N2 107.4(3) . . ?
N1 B1 N2 108.3(3) . . ?
N4 C18 H12 109.5 . . ?
N4 C18 H11 109.5 . . ?
H12 C18 H11 109.5 . . ?
N4 C18 H13 109.5 . . ?
H12 C18 H13 109.5 . . ?
H11 C18 H13 109.5 . . ?
N3 C19 H16 109.5 . . ?
N3 C19 H15 109.5 . . ?
H16 C19 H15 109.5 . . ?
N3 C19 H14 109.5 . . ?
H16 C19 H14 109.5 . . ?
H15 C19 H14 109.5 . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.049

_shelxl_version_number           2014-3



_chemical_properties_physical    Hygroscopic
_exptl_crystal_preparation       Luminescent
