# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_HNBPh3
_database_code_depnum_ccdc_archive 'CCDC 1562257'
_audit_update_record             
;
2017-07-14 deposited with the CCDC.
2017-10-03 downloaded from the CCDC.
;
_audit_creation_date             2017-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '1(C18 H18 B3 N3)'
_chemical_formula_sum            'C18 H18 B3 N3'
_chemical_formula_weight         308.81
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           184
_space_group_name_H-M_alt        'P 6 c c'
_space_group_name_Hall           'P 6 -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z'
'-y, x-y, z'
'-x, -y, z'
'-x+y, -x, z'
'y, -x+y, z'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'-y, -x, z+1/2'
'y, x, z+1/2'
'x-y, -y, z+1/2'
'-x, -x+y, z+1/2'

_cell_length_a                   17.1231(6)
_cell_length_b                   17.1231(6)
_cell_length_c                   7.1049(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1804.07(15)
_cell_formula_units_Z            3.9996
_cell_measurement_reflns_used    8545
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.71
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0666 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.9038. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.637
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.204
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            38173
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.925
_diffrn_reflns_theta_min         1.373
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.822
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                1364
_reflns_number_total             1441
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         1441
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0285
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+0.0952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0773
_refine_special_details          
'Squeeze was applied to remove disordered solvent that could not be sensibly modelled.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
B1 B 0.57673(10) 0.32119(10) 0.5579(2) 0.0175(3) Uani 1 1 d . . . . .
C1 C 0.47881(8) 0.30684(8) 0.54135(18) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.40311(9) 0.22665(9) 0.6001(2) 0.0194(3) Uani 1 1 d . . . . .
H2 H 0.4113 0.1817 0.6605 0.023 Uiso 1 1 calc R . . . .
C3 C 0.31610(9) 0.21134(9) 0.5720(2) 0.0214(3) Uani 1 1 d . . . . .
H3 H 0.2657 0.1567 0.6141 0.026 Uiso 1 1 calc R . . . .
C4 C 0.30312(9) 0.27585(10) 0.4826(2) 0.0225(3) Uani 1 1 d . . . . .
H4 H 0.2437 0.2650 0.4617 0.027 Uiso 1 1 calc R . . . .
C5 C 0.37673(10) 0.35638(9) 0.4233(2) 0.0229(3) Uani 1 1 d . . . . .
H5 H 0.3679 0.4007 0.3623 0.028 Uiso 1 1 calc R . . . .
C6 C 0.46356(10) 0.37166(9) 0.4538(2) 0.0204(3) Uani 1 1 d . . . . .
H6 H 0.5137 0.4272 0.4145 0.024 Uiso 1 1 calc R . . . .
N1 N 0.65489(7) 0.40860(7) 0.56103(18) 0.0174(3) Uani 1 1 d . . . . .
H1 H 0.6482(12) 0.4566(14) 0.559(4) 0.033(5) 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
B1 C1 1.5727(18) . ?
B1 N1 1.4250(17) 3_655 ?
B1 N1 1.4244(17) . ?
C1 C2 1.4000(18) . ?
C1 C6 1.4061(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.3921(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3917(19) . ?
C6 H6 0.9500 . ?
N1 B1 1.4250(17) 5_665 ?
N1 H1 0.88(2) . ?

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
N1 B1 C1 120.96(12) 3_655 . ?
N1 B1 C1 122.24(12) . . ?
N1 B1 N1 116.72(13) . 3_655 ?
C2 C1 B1 121.52(11) . . ?
C2 C1 C6 117.39(12) . . ?
C6 C1 B1 120.93(12) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.38(12) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.93(13) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.19(13) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.56(13) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.53(13) . . ?
C5 C6 H6 119.2 . . ?
B1 N1 B1 123.23(13) . 5_665 ?
B1 N1 H1 119.1(12) . . ?
B1 N1 H1 117.6(12) 5_665 . ?

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
B1 C1 C2 C3 -174.97(14) . . . . ?
B1 C1 C6 C5 174.26(14) . . . . ?
C1 B1 N1 B1 -173.84(8) . . . 5_665 ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C1 C6 C5 -1.1(2) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C6 C1 C2 C3 0.40(19) . . . . ?
N1 B1 C1 C2 24.9(2) 3_655 . . . ?
N1 B1 C1 C2 -158.28(14) . . . . ?
N1 B1 C1 C6 26.5(2) . . . . ?
N1 B1 C1 C6 -150.26(14) 3_655 . . . ?
N1 B1 N1 B1 3.1(3) 3_655 . . 5_665 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_HNBpCF3C6H4
_database_code_depnum_ccdc_archive 'CCDC 1562258'
_audit_update_record             
;
2017-07-14 deposited with the CCDC.
2017-10-03 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT213_HNBpCF3C6H4         
;
PROBLEM: Atom F4A             has ADP max/min Ratio .....        4.5 prolat
RESPONSE: The CF3 groups were disordered.
;
# Added during the CSD deposition process: Friday 14 July 2017 02:31 PM
# end Validation Reply Form

_audit_creation_date             2016-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H15 B3 F9 N3'
_chemical_formula_sum            'C21 H15 B3 F9 N3'
_chemical_formula_weight         512.79
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.0171(3)
_cell_length_b                   23.4105(6)
_cell_length_c                   8.7127(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.1234(15)
_cell_angle_gamma                90
_cell_volume                     2218.71(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5196
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.48
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0516 before and 0.0408 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0554 before and 0.0420 after correction.
 The Ratio of minimum to maximum transmission is 0.90.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 53276 reflections, Rint = 0.0533
 (18668 with I > 3sig(I), Rint = 0.0292)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5313
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.954
_diffrn_reflns_theta_min         1.740
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4009
_reflns_number_total             5313
_reflns_special_details          
;
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5313
_refine_ls_number_restraints     243
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0584
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²+2.1056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1482
_refine_special_details          
;
Refined as a two component twin against and hklf5 file, BASF 0.436.
Occupancies of disordered CF3 groups refined against free variables
and fixed.  Some restraints on distance and thermal parameters
applied to disordered CF3 groups to maintain sensible geometries.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5642(16) 0.4358(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 F7-C21 \\sim F7A-C21 \\sim F8-C21 \\sim F8A-C21 \\sim F9-C21 \\sim F9A-C21
 with sigma of 0.01
 F3-C7 \\sim F3A-C7 \\sim F1-C7 \\sim F1A-C7 \\sim F2-C7 \\sim F2A-C7
 with sigma of 0.01
 F6-C14 \\sim F6A-C14 \\sim F5-C14 \\sim F5A-C14 \\sim F4-C14 \\sim F4A-C14
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
F7 \\sim F7A \\sim F8 \\sim F8A \\sim F9 \\sim F9A \\sim C21: within 2A with
sigma of 0.003 and sigma for terminal atoms of 0.006
F3 \\sim F3A \\sim F1 \\sim F1A \\sim F2 \\sim F2A \\sim C7: within 2A with
sigma of 0.003 and sigma for terminal atoms of 0.006
F5 \\sim F5A \\sim F4 \\sim F4A \\sim F6 \\sim F6A \\sim C14: within 2A with
sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(F1A) = Uanis(F1)
5. Others
 Fixed Sof: F1(0.48383) F2(0.48383) F3(0.48383) F4(0.56495) F5(0.56495)
 F6(0.56495) F7(0.55284) F8(0.55284) F9(0.55284) F6A(0.43505) F4A(0.43505)
 F5A(0.43505) F2A(0.51617) F3A(0.51617) F1A(0.51617) F8A(0.44716) F7A(0.44716)
 F9A(0.44716)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3A), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C16(H16), C17(H17), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
F1 F 0.5447(13) 1.0884(6) 0.2836(14) 0.0416(12) Uani 0.4838 1 d D U P A 1
F2 F 0.6188(5) 1.0576(3) 0.0934(5) 0.0461(12) Uani 0.4838 1 d D U P A 1
F3 F 0.7450(6) 1.0763(4) 0.3054(8) 0.0543(16) Uani 0.4838 1 d D U P A 1
F4 F 1.0588(5) 0.54391(18) 0.3642(7) 0.0516(12) Uani 0.565 1 d D U P B 1
F5 F 0.982(2) 0.5397(5) 0.1282(13) 0.0434(16) Uani 0.565 1 d D U P B 1
F6 F 0.9163(5) 0.48391(17) 0.2953(6) 0.0556(12) Uani 0.565 1 d D U P B 1
F7 F -0.0374(10) 0.7162(3) 0.9163(7) 0.0359(14) Uani 0.5528 1 d D U P C 1
F8 F -0.0005(6) 0.6282(2) 0.8811(6) 0.0433(11) Uani 0.5528 1 d D U P C 1
F9 F -0.1205(9) 0.6782(3) 0.7076(14) 0.0410(15) Uani 0.5528 1 d D U P C 1
N1 N 0.6281(2) 0.77322(9) 0.3923(3) 0.0228(5) Uani 1 1 d . . . . .
N2 N 0.5052(2) 0.70114(9) 0.4943(3) 0.0215(5) Uani 1 1 d . . . . .
N3 N 0.4476(2) 0.80108(9) 0.5014(3) 0.0212(5) Uani 1 1 d . . . . .
C1 C 0.5703(3) 0.88192(11) 0.3839(3) 0.0213(5) Uani 1 1 d . . . . .
C2 C 0.4735(2) 0.92019(11) 0.3447(4) 0.0271(6) Uani 1 1 d . . . . .
H2A H 0.3918 0.9075 0.3465 0.033 Uiso 1 1 calc R . . . .
C3 C 0.4925(3) 0.97625(12) 0.3033(4) 0.0302(7) Uani 1 1 d . . . . .
H3A H 0.4250 1.0014 0.2756 0.036 Uiso 1 1 calc R . . . .
C4 C 0.6126(3) 0.99503(11) 0.3029(4) 0.0264(6) Uani 1 1 d . . . . .
C5 C 0.7115(3) 0.95854(11) 0.3433(4) 0.0274(6) Uani 1 1 d . . . . .
H5 H 0.7932 0.9717 0.3444 0.033 Uiso 1 1 calc R . . . .
C6 C 0.6896(3) 0.90258(11) 0.3823(4) 0.0261(6) Uani 1 1 d . . . . .
H6 H 0.7573 0.8774 0.4087 0.031 Uiso 1 1 calc R . . . .
C7 C 0.6357(3) 1.05444(12) 0.2526(4) 0.0389(7) Uani 1 1 d D U . . .
C8 C 0.7007(2) 0.66639(10) 0.3822(3) 0.0203(5) Uani 1 1 d . . . . .
C9 C 0.7813(3) 0.67683(11) 0.2774(3) 0.0257(6) Uani 1 1 d . . . . .
H9 H 0.7810 0.7134 0.2301 0.031 Uiso 1 1 calc R . . . .
C10 C 0.8621(3) 0.63537(12) 0.2396(4) 0.0285(6) Uani 1 1 d . . . . .
H10 H 0.9170 0.6436 0.1688 0.034 Uiso 1 1 calc R . . . .
C11 C 0.8610(3) 0.58165(11) 0.3075(4) 0.0255(6) Uani 1 1 d . . . . .
C12 C 0.7834(3) 0.57008(11) 0.4136(4) 0.0261(6) Uani 1 1 d . . . . .
H12 H 0.7842 0.5335 0.4612 0.031 Uiso 1 1 calc R . . . .
C13 C 0.7046(3) 0.61216(11) 0.4498(3) 0.0234(6) Uani 1 1 d . . . . .
H13 H 0.6515 0.6039 0.5228 0.028 Uiso 1 1 calc R . . . .
C14 C 0.9469(3) 0.53670(13) 0.2664(4) 0.0447(8) Uani 1 1 d D U . . .
C15 C 0.3052(2) 0.72612(10) 0.6092(3) 0.0204(5) Uani 1 1 d . . . . .
C16 C 0.2581(3) 0.67015(11) 0.5963(3) 0.0267(6) Uani 1 1 d . . . . .
H16 H 0.2978 0.6422 0.5426 0.032 Uiso 1 1 calc R . . . .
C17 C 0.1558(3) 0.65473(11) 0.6596(4) 0.0282(6) Uani 1 1 d . . . . .
H17 H 0.1253 0.6167 0.6489 0.034 Uiso 1 1 calc R . . . .
C18 C 0.0976(2) 0.69516(11) 0.7391(3) 0.0234(6) Uani 1 1 d . . . . .
C19 C 0.1410(2) 0.75061(12) 0.7536(3) 0.0244(6) Uani 1 1 d . . . . .
H19 H 0.1008 0.7783 0.8077 0.029 Uiso 1 1 calc R . . . .
C20 C 0.2433(2) 0.76552(10) 0.6888(3) 0.0228(6) Uani 1 1 d . . . . .
H20 H 0.2724 0.8038 0.6989 0.027 Uiso 1 1 calc R . . . .
C21 C -0.0136(3) 0.67817(11) 0.8064(3) 0.0340(7) Uani 1 1 d D U . . .
B1 B 0.5486(3) 0.81779(12) 0.4276(4) 0.0207(6) Uani 1 1 d . . . . .
B2 B 0.6099(3) 0.71403(12) 0.4233(4) 0.0204(6) Uani 1 1 d . . . . .
B3 B 0.4215(3) 0.74279(12) 0.5353(3) 0.0200(6) Uani 1 1 d . . . . .
H2 H 0.494(3) 0.6694(14) 0.513(4) 0.026(8) Uiso 1 1 d . . . . .
H3 H 0.399(3) 0.8256(14) 0.523(4) 0.026(8) Uiso 1 1 d . . . . .
H1 H 0.686(3) 0.7818(14) 0.349(4) 0.031(9) Uiso 1 1 d . . . . .
F6A F 0.8770(6) 0.4881(2) 0.2267(8) 0.0533(13) Uani 0.435 1 d D U P B 2
F4A F 1.0418(7) 0.5217(3) 0.3704(10) 0.0607(15) Uani 0.435 1 d D U P B 2
F5A F 0.978(2) 0.5499(6) 0.1288(16) 0.0388(18) Uani 0.435 1 d D U P B 2
F2A F 0.6794(5) 1.0565(3) 0.1191(7) 0.0580(13) Uani 0.5162 1 d D U P A 2
F3A F 0.7259(5) 1.0788(3) 0.3607(6) 0.0433(14) Uani 0.5162 1 d D U P A 2
F1A F 0.5468(12) 1.0927(6) 0.2541(13) 0.0416(12) Uani 0.5162 1 d D U P A 2
F8A F -0.0252(7) 0.6212(2) 0.8181(8) 0.0442(14) Uani 0.4472 1 d D U P C 2
F7A F -0.0271(14) 0.7036(4) 0.9398(9) 0.0404(17) Uani 0.4472 1 d D U P C 2
F9A F -0.1145(10) 0.6922(4) 0.7023(17) 0.0344(16) Uani 0.4472 1 d D U P C 2


_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
F1 C7 1.340(6) . ?
F2 C7 1.372(5) . ?
F3 C7 1.321(6) . ?
F4 C14 1.394(5) . ?
F5 C14 1.326(6) . ?
F6 C14 1.316(5) . ?
F7 C21 1.363(5) . ?
F8 C21 1.335(5) . ?
F9 C21 1.344(6) . ?
N1 B1 1.427(4) . ?
N1 B2 1.432(4) . ?
N1 H1 0.82(4) . ?
N2 B2 1.425(4) . ?
N2 B3 1.426(4) . ?
N2 H2 0.77(3) . ?
N3 B1 1.425(4) . ?
N3 B3 1.435(4) . ?
N3 H3 0.83(3) . ?
C1 C2 1.394(4) . ?
C1 C6 1.402(4) . ?
C1 B1 1.576(4) . ?
C2 H2A 0.9500 . ?
C2 C3 1.386(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.395(4) . ?
C4 C5 1.385(4) . ?
C4 C7 1.492(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(4) . ?
C6 H6 0.9500 . ?
C7 F2A 1.329(5) . ?
C7 F3A 1.379(5) . ?
C7 F1A 1.329(6) . ?
C8 C9 1.393(4) . ?
C8 C13 1.397(4) . ?
C8 B2 1.576(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(4) . ?
C11 C12 1.382(4) . ?
C11 C14 1.495(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(4) . ?
C13 H13 0.9500 . ?
C14 F6A 1.386(6) . ?
C14 F4A 1.318(6) . ?
C14 F5A 1.335(7) . ?
C15 C16 1.408(3) . ?
C15 C20 1.395(4) . ?
C15 B3 1.571(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(4) . ?
C18 C19 1.382(4) . ?
C18 C21 1.494(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(4) . ?
C20 H20 0.9500 . ?
C21 F8A 1.346(5) . ?
C21 F7A 1.334(6) . ?
C21 F9A 1.359(6) . ?

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
B1 N1 B2 124.0(3) . . ?
B1 N1 H1 118(2) . . ?
B2 N1 H1 118(2) . . ?
B2 N2 B3 124.3(2) . . ?
B2 N2 H2 117(2) . . ?
B3 N2 H2 118(2) . . ?
B1 N3 B3 123.4(2) . . ?
B1 N3 H3 120(2) . . ?
B3 N3 H3 117(2) . . ?
C2 C1 C6 117.3(2) . . ?
C2 C1 B1 122.1(2) . . ?
C6 C1 B1 120.6(2) . . ?
C1 C2 H2A 119.0 . . ?
C3 C2 C1 122.1(3) . . ?
C3 C2 H2A 119.0 . . ?
C2 C3 H3A 120.6 . . ?
C2 C3 C4 118.8(3) . . ?
C4 C3 H3A 120.6 . . ?
C3 C4 C7 120.0(3) . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 C7 119.1(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 H6 119.0 . . ?
C5 C6 C1 121.9(3) . . ?
C5 C6 H6 119.0 . . ?
F1 C7 F2 100.7(6) . . ?
F1 C7 C4 109.0(7) . . ?
F2 C7 C4 110.2(3) . . ?
F3 C7 F1 111.7(9) . . ?
F3 C7 F2 107.5(5) . . ?
F3 C7 C4 116.5(5) . . ?
F2A C7 C4 113.1(4) . . ?
F2A C7 F3A 105.1(4) . . ?
F3A C7 C4 108.8(4) . . ?
F1A C7 C4 117.7(7) . . ?
F1A C7 F2A 110.8(6) . . ?
F1A C7 F3A 99.7(8) . . ?
C9 C8 C13 117.1(2) . . ?
C9 C8 B2 121.2(2) . . ?
C13 C8 B2 121.7(2) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 122.1(2) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.8(3) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 C14 119.1(3) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 C14 120.3(2) . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.4(2) . . ?
C13 C12 H12 120.3 . . ?
C8 C13 H13 119.0 . . ?
C12 C13 C8 122.0(3) . . ?
C12 C13 H13 119.0 . . ?
F4 C14 C11 107.5(3) . . ?
F5 C14 F4 100.8(11) . . ?
F5 C14 C11 118.0(7) . . ?
F6 C14 F4 103.0(4) . . ?
F6 C14 F5 110.2(7) . . ?
F6 C14 C11 115.1(3) . . ?
F6A C14 C11 106.9(3) . . ?
F4A C14 C11 119.0(5) . . ?
F4A C14 F6A 107.6(4) . . ?
F4A C14 F5A 113.0(13) . . ?
F5A C14 C11 108.3(8) . . ?
F5A C14 F6A 100.3(10) . . ?
C16 C15 B3 120.9(2) . . ?
C20 C15 C16 116.8(2) . . ?
C20 C15 B3 122.3(2) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.8(3) . . ?
C17 C16 H16 119.1 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.5(2) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C21 119.1(2) . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 C21 120.5(2) . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.5(2) . . ?
C20 C19 H19 120.3 . . ?
C15 C20 H20 119.0 . . ?
C19 C20 C15 122.0(2) . . ?
C19 C20 H20 119.0 . . ?
F7 C21 C18 111.3(5) . . ?
F8 C21 F7 104.4(4) . . ?
F8 C21 F9 109.2(5) . . ?
F8 C21 C18 113.1(3) . . ?
F9 C21 F7 101.7(8) . . ?
F9 C21 C18 116.0(7) . . ?
F8A C21 C18 112.8(4) . . ?
F8A C21 F9A 102.3(5) . . ?
F7A C21 C18 115.8(7) . . ?
F7A C21 F8A 110.5(6) . . ?
F7A C21 F9A 106.3(10) . . ?
F9A C21 C18 108.0(7) . . ?
N1 B1 C1 121.5(3) . . ?
N3 B1 N1 116.5(2) . . ?
N3 B1 C1 122.0(2) . . ?
N1 B2 C8 122.0(3) . . ?
N2 B2 N1 115.7(3) . . ?
N2 B2 C8 122.3(2) . . ?
N2 B3 N3 116.1(2) . . ?
N2 B3 C15 122.3(2) . . ?
N3 B3 C15 121.6(2) . . ?

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
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C1 B1 N1 147.9(3) . . . . ?
C2 C1 B1 N3 -30.8(4) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C2 C3 C4 C7 177.5(3) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C3 C4 C7 F1 28.8(8) . . . . ?
C3 C4 C7 F2 -80.8(4) . . . . ?
C3 C4 C7 F3 156.4(5) . . . . ?
C3 C4 C7 F2A -111.6(4) . . . . ?
C3 C4 C7 F3A 132.0(4) . . . . ?
C3 C4 C7 F1A 19.7(8) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
C5 C4 C7 F1 -153.5(7) . . . . ?
C5 C4 C7 F2 96.9(4) . . . . ?
C5 C4 C7 F3 -25.9(5) . . . . ?
C5 C4 C7 F2A 66.1(5) . . . . ?
C5 C4 C7 F3A -50.3(5) . . . . ?
C5 C4 C7 F1A -162.6(7) . . . . ?
C6 C1 C2 C3 1.0(4) . . . . ?
C6 C1 B1 N1 -31.7(4) . . . . ?
C6 C1 B1 N3 149.5(3) . . . . ?
C7 C4 C5 C6 -176.7(3) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
C9 C8 C13 C12 -0.8(4) . . . . ?
C9 C8 B2 N1 -18.0(4) . . . . ?
C9 C8 B2 N2 162.4(3) . . . . ?
C9 C10 C11 C12 -1.7(5) . . . . ?
C9 C10 C11 C14 179.5(3) . . . . ?
C10 C11 C12 C13 1.3(4) . . . . ?
C10 C11 C14 F4 85.7(4) . . . . ?
C10 C11 C14 F5 -27.3(11) . . . . ?
C10 C11 C14 F6 -160.2(4) . . . . ?
C10 C11 C14 F6A -129.9(4) . . . . ?
C10 C11 C14 F4A 108.1(5) . . . . ?
C10 C11 C14 F5A -22.7(13) . . . . ?
C11 C12 C13 C8 0.0(4) . . . . ?
C12 C11 C14 F4 -93.1(4) . . . . ?
C12 C11 C14 F5 153.9(11) . . . . ?
C12 C11 C14 F6 21.0(5) . . . . ?
C12 C11 C14 F6A 51.2(5) . . . . ?
C12 C11 C14 F4A -70.7(5) . . . . ?
C12 C11 C14 F5A 158.4(12) . . . . ?
C13 C8 C9 C10 0.4(4) . . . . ?
C13 C8 B2 N1 161.5(3) . . . . ?
C13 C8 B2 N2 -18.1(4) . . . . ?
C14 C11 C12 C13 -179.9(3) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C16 C15 C20 C19 0.5(4) . . . . ?
C16 C15 B3 N2 -19.1(4) . . . . ?
C16 C15 B3 N3 159.2(3) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C16 C17 C18 C21 179.6(3) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C17 C18 C21 F7 162.1(4) . . . . ?
C17 C18 C21 F8 45.0(4) . . . . ?
C17 C18 C21 F9 -82.3(6) . . . . ?
C17 C18 C21 F8A 17.1(5) . . . . ?
C17 C18 C21 F7A 145.8(5) . . . . ?
C17 C18 C21 F9A -95.2(6) . . . . ?
C18 C19 C20 C15 -0.3(4) . . . . ?
C19 C18 C21 F7 -18.9(5) . . . . ?
C19 C18 C21 F8 -136.0(4) . . . . ?
C19 C18 C21 F9 96.7(6) . . . . ?
C19 C18 C21 F8A -163.9(4) . . . . ?
C19 C18 C21 F7A -35.2(6) . . . . ?
C19 C18 C21 F9A 83.8(6) . . . . ?
C20 C15 C16 C17 -0.2(4) . . . . ?
C20 C15 B3 N2 161.5(3) . . . . ?
C20 C15 B3 N3 -20.2(4) . . . . ?
C21 C18 C19 C20 -179.3(3) . . . . ?
B1 N1 B2 N2 -0.3(4) . . . . ?
B1 N1 B2 C8 -179.9(3) . . . . ?
B1 N3 B3 N2 1.6(4) . . . . ?
B1 N3 B3 C15 -176.9(2) . . . . ?
B1 C1 C2 C3 -178.7(3) . . . . ?
B1 C1 C6 C5 179.5(3) . . . . ?
B2 N1 B1 N3 1.6(4) . . . . ?
B2 N1 B1 C1 -177.3(3) . . . . ?
B2 N2 B3 N3 -0.1(4) . . . . ?
B2 N2 B3 C15 178.3(3) . . . . ?
B2 C8 C9 C10 180.0(3) . . . . ?
B2 C8 C13 C12 179.6(3) . . . . ?
B3 N2 B2 N1 -0.5(4) . . . . ?
B3 N2 B2 C8 179.2(3) . . . . ?
B3 N3 B1 N1 -2.2(4) . . . . ?
B3 N3 B1 C1 176.6(2) . . . . ?
B3 C15 C16 C17 -179.6(3) . . . . ?
B3 C15 C20 C19 180.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5642(16)
2 0.4358(16)


