# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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 2521021'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H30 B2 F4 N6'
_chemical_formula_weight         476.14

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   24.988(3)
_cell_length_b                   6.5629(7)
_cell_length_c                   16.5307(17)
_cell_angle_alpha                90
_cell_angle_beta                 122.402(3)
_cell_angle_gamma                90
_cell_volume                     2288.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      28.81

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9448
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17856
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.919
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2241
_reflns_number_gt                1906
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0274P)²+3.5877P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2241
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_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
F1 F 0.22292(4) 0.63222(15) 0.56642(7) 0.0241(2) Uani 1 1 d . . . . .
F2 F 0.28124(5) 0.40948(14) 0.68762(7) 0.0242(2) Uani 1 1 d . . . . .
N1 N 0.30971(6) 0.46202(19) 0.56998(9) 0.0150(3) Uani 1 1 d . . . . .
N2 N 0.40697(6) 0.6348(2) 0.66063(9) 0.0180(3) Uani 1 1 d . . . . .
N3 N 0.32767(6) 0.72839(19) 0.69152(9) 0.0156(3) Uani 1 1 d . . . . .
C1 C 0.26255(7) 0.3411(2) 0.48569(10) 0.0162(3) Uani 1 1 d . . . . .
H1A H 0.282349 0.290659 0.451264 0.019 Uiso 1 1 calc R U . . .
H1B H 0.226585 0.430144 0.441376 0.019 Uiso 1 1 calc R U . . .
C2 C 0.36887(7) 0.5038(2) 0.59239(10) 0.0154(3) Uani 1 1 d . . . . .
C3 C 0.38652(7) 0.7493(2) 0.70685(11) 0.0173(3) Uani 1 1 d . . . . .
C4 C 0.42731(8) 0.8980(3) 0.77339(11) 0.0221(3) Uani 1 1 d . . . . .
H4 H 0.469154 0.912723 0.786867 0.027 Uiso 1 1 calc R U . . .
C5 C 0.40694(8) 1.0209(3) 0.81846(12) 0.0234(4) Uani 1 1 d . . . . .
H5 H 0.434306 1.122197 0.862209 0.028 Uiso 1 1 calc R U . . .
C6 C 0.34555(8) 0.9970(2) 0.79992(11) 0.0207(3) Uani 1 1 d . . . . .
H6 H 0.330766 1.081477 0.830637 0.025 Uiso 1 1 calc R U . . .
C7 C 0.30775(7) 0.8506(2) 0.73716(11) 0.0181(3) Uani 1 1 d . . . . .
H7 H 0.266238 0.832710 0.724628 0.022 Uiso 1 1 calc R U . . .
C8 C 0.39992(7) 0.4043(2) 0.54238(11) 0.0174(3) Uani 1 1 d . . . . .
C9 C 0.40093(8) 0.1706(2) 0.55117(12) 0.0218(4) Uani 1 1 d . . . . .
H9A H 0.423365 0.111637 0.523028 0.033 Uiso 1 1 calc R U . . .
H9B H 0.357353 0.119025 0.517154 0.033 Uiso 1 1 calc R U . . .
H9C H 0.422704 0.132516 0.618944 0.033 Uiso 1 1 calc R U . . .
C10 C 0.36747(8) 0.4772(3) 0.43751(11) 0.0211(3) Uani 1 1 d . . . . .
H10A H 0.392020 0.430719 0.410579 0.032 Uiso 1 1 calc R U . . .
H10B H 0.365266 0.626356 0.435528 0.032 Uiso 1 1 calc R U . . .
H10C H 0.324514 0.420801 0.399869 0.032 Uiso 1 1 calc R U . . .
C11 C 0.46952(7) 0.4735(3) 0.59245(12) 0.0242(4) Uani 1 1 d . . . . .
H11A H 0.492109 0.436335 0.660401 0.036 Uiso 1 1 calc R U . . .
H11B H 0.471100 0.621642 0.586456 0.036 Uiso 1 1 calc R U . . .
H11C H 0.489625 0.406681 0.562350 0.036 Uiso 1 1 calc R U . . .
B1 B 0.28359(8) 0.5546(3) 0.62719(12) 0.0175(4) 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
F1 B1 1.3911(19) . ?
F2 B1 1.4040(19) . ?
N1 C2 1.3455(19) . ?
N1 C1 1.4834(19) . ?
N1 B1 1.533(2) . ?
N2 C2 1.329(2) . ?
N2 C3 1.352(2) . ?
N3 C3 1.3587(19) . ?
N3 C7 1.3650(19) . ?
N3 B1 1.546(2) . ?
C1 C1 1.538(3) 7_556 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C8 1.549(2) . ?
C3 C4 1.414(2) . ?
C4 C5 1.368(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.357(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.539(2) . ?
C8 C11 1.541(2) . ?
C8 C10 1.544(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
C2 N1 C1 124.77(12) . . ?
C2 N1 B1 121.16(12) . . ?
C1 N1 B1 113.88(12) . . ?
C2 N2 C3 121.55(13) . . ?
C3 N3 C7 121.10(13) . . ?
C3 N3 B1 120.25(13) . . ?
C7 N3 B1 118.52(13) . . ?
N1 C1 C1 112.13(15) . 7_556 ?
N1 C1 H1A 109.2 . . ?
C1 C1 H1A 109.2 7_556 . ?
N1 C1 H1B 109.2 . . ?
C1 C1 H1B 109.2 7_556 . ?
H1A C1 H1B 107.9 . . ?
N2 C2 N1 123.16(13) . . ?
N2 C2 C8 112.93(13) . . ?
N1 C2 C8 123.91(13) . . ?
N2 C3 N3 122.52(14) . . ?
N2 C3 C4 119.34(14) . . ?
N3 C3 C4 118.14(14) . . ?
C5 C4 C3 120.48(15) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.85(15) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 118.54(14) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 N3 121.88(14) . . ?
C6 C7 H7 119.1 . . ?
N3 C7 H7 119.1 . . ?
C9 C8 C11 106.66(13) . . ?
C9 C8 C10 112.76(13) . . ?
C11 C8 C10 105.92(13) . . ?
C9 C8 C2 110.91(12) . . ?
C11 C8 C2 109.45(12) . . ?
C10 C8 C2 110.88(12) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
F1 B1 F2 108.50(13) . . ?
F1 B1 N1 111.05(13) . . ?
F2 B1 N1 111.34(13) . . ?
F1 B1 N3 109.01(13) . . ?
F2 B1 N3 107.28(12) . . ?
N1 B1 N3 109.56(12) . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2521023'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H34 B2 F4 N6'
_chemical_formula_weight         504.19

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'
F F 0.0171 0.0103 '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'

_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+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                   6.9879(4)
_cell_length_b                   16.3090(12)
_cell_length_c                   21.8166(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2486.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8479
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      28.28

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.088
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9097
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14845
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.667
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2441
_reflns_number_gt                2097
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0287P)²+1.7498P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2441
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
F1 F 0.37029(14) 0.58919(6) 0.52764(4) 0.0272(3) Uani 1 1 d . . . . .
F2 F 0.16821(13) 0.66259(6) 0.46754(5) 0.0272(3) Uani 1 1 d . . . . .
N1 N 0.46960(17) 0.62121(7) 0.42598(5) 0.0133(3) Uani 1 1 d . . . . .
N2 N 0.37496(18) 0.52260(8) 0.35162(6) 0.0153(3) Uani 1 1 d . . . . .
N3 N 0.20980(17) 0.51774(8) 0.44527(5) 0.0132(3) Uani 1 1 d . . . . .
C1 C 0.7720(2) 0.66780(10) 0.35101(7) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.6455(2) 0.60820(9) 0.33301(7) 0.0164(3) Uani 1 1 d . . . . .
H2 H 0.661536 0.582782 0.294170 0.020 Uiso 1 1 calc R U . . .
C3 C 0.4919(2) 0.58373(9) 0.37092(7) 0.0142(3) Uani 1 1 d . . . . .
C4 C 0.5925(2) 0.68202(9) 0.44379(7) 0.0160(3) Uani 1 1 d . . . . .
H4 H 0.572740 0.708152 0.482187 0.019 Uiso 1 1 calc R U . . .
C5 C 0.7421(2) 0.70622(9) 0.40827(7) 0.0166(3) Uani 1 1 d . . . . .
H5 H 0.825516 0.748500 0.421793 0.020 Uiso 1 1 calc R U . . .
C6 C 0.9398(2) 0.69113(11) 0.31145(8) 0.0256(4) Uani 1 1 d . . . . .
H6A H 1.057440 0.668417 0.329054 0.038 Uiso 1 1 calc R U . . .
H6B H 0.949927 0.751007 0.309482 0.038 Uiso 1 1 calc R U . . .
H6C H 0.921328 0.669164 0.270064 0.038 Uiso 1 1 calc R U . . .
C7 C 0.2475(2) 0.48843(9) 0.38870(6) 0.0133(3) Uani 1 1 d . . . . .
C8 C 0.1522(2) 0.41121(9) 0.36115(7) 0.0147(3) Uani 1 1 d . . . . .
C9 C -0.0679(2) 0.41742(10) 0.36119(7) 0.0189(3) Uani 1 1 d . . . . .
H9A H -0.114593 0.417754 0.403539 0.028 Uiso 1 1 calc R U . . .
H9B H -0.121999 0.370275 0.339387 0.028 Uiso 1 1 calc R U . . .
H9C H -0.106956 0.468174 0.340657 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2237(2) 0.33383(9) 0.39471(7) 0.0181(3) Uani 1 1 d . . . . .
H10A H 0.363621 0.335142 0.397357 0.027 Uiso 1 1 calc R U . . .
H10B H 0.183500 0.284922 0.372001 0.027 Uiso 1 1 calc R U . . .
H10C H 0.169262 0.332253 0.436095 0.027 Uiso 1 1 calc R U . . .
C11 C 0.2132(2) 0.40144(10) 0.29373(7) 0.0197(3) Uani 1 1 d . . . . .
H11A H 0.172691 0.449749 0.270379 0.030 Uiso 1 1 calc R U . . .
H11B H 0.153035 0.352323 0.276449 0.030 Uiso 1 1 calc R U . . .
H11C H 0.352681 0.396015 0.291441 0.030 Uiso 1 1 calc R U . . .
C12 C 0.0902(2) 0.47517(9) 0.49171(7) 0.0138(3) Uani 1 1 d . . . . .
H12A H 0.167046 0.465999 0.529214 0.017 Uiso 1 1 calc R U . . .
H12B H 0.051415 0.420923 0.475572 0.017 Uiso 1 1 calc R U . . .
B1 B 0.3001(2) 0.59771(11) 0.46847(8) 0.0173(4) 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
F1 B1 1.388(2) . ?
F2 B1 1.404(2) . ?
N1 C3 1.3567(19) . ?
N1 C4 1.3684(19) . ?
N1 B1 1.552(2) . ?
N2 C7 1.3263(19) . ?
N2 C3 1.3560(19) . ?
N3 C7 1.3494(18) . ?
N3 C12 1.4855(18) . ?
N3 B1 1.535(2) . ?
C1 C2 1.371(2) . ?
C1 C5 1.413(2) . ?
C1 C6 1.505(2) . ?
C2 C3 1.413(2) . ?
C2 H2 0.9500 . ?
C4 C5 1.360(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.546(2) . ?
C8 C11 1.540(2) . ?
C8 C9 1.541(2) . ?
C8 C10 1.542(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C12 1.541(3) 5_566 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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
C3 N1 C4 120.39(13) . . ?
C3 N1 B1 120.34(12) . . ?
C4 N1 B1 119.23(12) . . ?
C7 N2 C3 121.62(13) . . ?
C7 N3 C12 124.61(12) . . ?
C7 N3 B1 121.49(12) . . ?
C12 N3 B1 113.81(11) . . ?
C2 C1 C5 118.17(14) . . ?
C2 C1 C6 121.15(14) . . ?
C5 C1 C6 120.68(14) . . ?
C1 C2 C3 121.50(14) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
N2 C3 N1 122.47(13) . . ?
N2 C3 C2 118.94(13) . . ?
N1 C3 C2 118.57(13) . . ?
C5 C4 N1 122.08(14) . . ?
C5 C4 H4 119.0 . . ?
N1 C4 H4 119.0 . . ?
C4 C5 C1 119.27(14) . . ?
C4 C5 H5 120.4 . . ?
C1 C5 H5 120.4 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 N3 122.69(14) . . ?
N2 C7 C8 113.22(12) . . ?
N3 C7 C8 124.07(13) . . ?
C11 C8 C9 106.48(12) . . ?
C11 C8 C10 106.21(12) . . ?
C9 C8 C10 112.12(13) . . ?
C11 C8 C7 109.67(12) . . ?
C9 C8 C7 112.08(13) . . ?
C10 C8 C7 110.03(12) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C12 111.99(15) . 5_566 ?
N3 C12 H12A 109.2 . . ?
C12 C12 H12A 109.2 5_566 . ?
N3 C12 H12B 109.2 . . ?
C12 C12 H12B 109.2 5_566 . ?
H12A C12 H12B 107.9 . . ?
F1 B1 F2 108.73(13) . . ?
F1 B1 N3 111.52(13) . . ?
F2 B1 N3 111.46(13) . . ?
F1 B1 N1 108.10(13) . . ?
F2 B1 N1 107.84(13) . . ?
N3 B1 N1 109.07(12) . . ?

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
C5 C1 C2 C3 -1.7(2) . . . . ?
C6 C1 C2 C3 177.53(14) . . . . ?
C7 N2 C3 N1 -9.0(2) . . . . ?
C7 N2 C3 C2 169.46(14) . . . . ?
C4 N1 C3 N2 179.27(13) . . . . ?
B1 N1 C3 N2 -2.9(2) . . . . ?
C4 N1 C3 C2 0.8(2) . . . . ?
B1 N1 C3 C2 178.58(13) . . . . ?
C1 C2 C3 N2 -177.86(14) . . . . ?
C1 C2 C3 N1 0.7(2) . . . . ?
C3 N1 C4 C5 -1.2(2) . . . . ?
B1 N1 C4 C5 -179.07(14) . . . . ?
N1 C4 C5 C1 0.2(2) . . . . ?
C2 C1 C5 C4 1.2(2) . . . . ?
C6 C1 C5 C4 -177.99(15) . . . . ?
C3 N2 C7 N3 7.8(2) . . . . ?
C3 N2 C7 C8 -170.70(13) . . . . ?
C12 N3 C7 N2 -170.70(13) . . . . ?
B1 N3 C7 N2 5.5(2) . . . . ?
C12 N3 C7 C8 7.6(2) . . . . ?
B1 N3 C7 C8 -176.21(13) . . . . ?
N2 C7 C8 C11 -7.49(18) . . . . ?
N3 C7 C8 C11 174.06(13) . . . . ?
N2 C7 C8 C9 -125.53(14) . . . . ?
N3 C7 C8 C9 56.02(19) . . . . ?
N2 C7 C8 C10 108.99(14) . . . . ?
N3 C7 C8 C10 -69.46(18) . . . . ?
C7 N3 C12 C12 -117.09(17) . . . 5_566 ?
B1 N3 C12 C12 66.47(19) . . . 5_566 ?
C7 N3 B1 F1 -134.36(14) . . . . ?
C12 N3 B1 F1 42.20(17) . . . . ?
C7 N3 B1 F2 103.91(15) . . . . ?
C12 N3 B1 F2 -79.52(16) . . . . ?
C7 N3 B1 N1 -15.04(19) . . . . ?
C12 N3 B1 N1 161.52(12) . . . . ?
C3 N1 B1 F1 135.08(13) . . . . ?
C4 N1 B1 F1 -47.06(18) . . . . ?
C3 N1 B1 F2 -107.53(15) . . . . ?
C4 N1 B1 F2 70.32(17) . . . . ?
C3 N1 B1 N3 13.66(19) . . . . ?
C4 N1 B1 N3 -168.49(12) . . . . ?

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
C4 H4 F2 0.95 2.47 3.2318(18) 137.4 4_566
C12 H12B F2 0.99 2.40 3.0165(17) 119.9 5_566

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2521022'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H34 B2 F4 N6'
_chemical_formula_weight         504.19

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'
F F 0.0171 0.0103 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.5180(7)
_cell_length_b                   9.9642(7)
_cell_length_c                   13.3563(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.837(3)
_cell_angle_gamma                90
_cell_volume                     1248.08(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9312
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16610
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.442
_diffrn_reflns_theta_max         26.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2574
_reflns_number_gt                2351
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0465P)²+0.5981P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2574
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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
F1 F 0.49505(8) 0.20492(7) 0.54466(5) 0.01960(19) Uani 1 1 d . . . . .
F2 F 0.28346(8) 0.31059(7) 0.55028(5) 0.01923(19) Uani 1 1 d . . . . .
N1 N 0.40638(11) 0.20640(10) 0.70310(7) 0.0135(2) Uani 1 1 d . . . . .
N2 N 0.49904(11) 0.39553(10) 0.80370(8) 0.0158(2) Uani 1 1 d . . . . .
N3 N 0.50247(11) 0.41656(10) 0.62972(7) 0.0145(2) Uani 1 1 d . . . . .
C1 C 0.44919(13) 0.26801(12) 0.79469(9) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.44018(14) 0.19835(13) 0.88551(9) 0.0179(3) Uani 1 1 d . . . . .
H2 H 0.470766 0.240229 0.949416 0.021 Uiso 1 1 calc R U . . .
C3 C 0.38731(13) 0.07049(13) 0.88116(9) 0.0186(3) Uani 1 1 d . . . . .
H3 H 0.380404 0.023297 0.941935 0.022 Uiso 1 1 calc R U . . .
C4 C 0.34341(13) 0.00959(13) 0.78646(10) 0.0181(3) Uani 1 1 d . . . . .
H4 H 0.306292 -0.079103 0.783208 0.022 Uiso 1 1 calc R U . . .
C5 C 0.35355(13) 0.07705(12) 0.69815(9) 0.0158(3) Uani 1 1 d . . . . .
C6 C 0.30788(15) 0.01180(13) 0.59659(9) 0.0199(3) Uani 1 1 d . . . . .
H6A H 0.392271 -0.018018 0.569746 0.030 Uiso 1 1 calc R U . . .
H6B H 0.254389 0.076499 0.549541 0.030 Uiso 1 1 calc R U . . .
H6C H 0.247162 -0.065694 0.604139 0.030 Uiso 1 1 calc R U . . .
C7 C 0.52669(12) 0.46546(12) 0.72498(9) 0.0139(2) Uani 1 1 d . . . . .
C8 C 0.59049(13) 0.60549(12) 0.75415(9) 0.0170(3) Uani 1 1 d . . . . .
C9 C 0.57031(16) 0.64052(14) 0.86306(10) 0.0237(3) Uani 1 1 d . . . . .
H9A H 0.611988 0.728864 0.881705 0.036 Uiso 1 1 calc R U . . .
H9B H 0.617796 0.572751 0.910265 0.036 Uiso 1 1 calc R U . . .
H9C H 0.468315 0.642260 0.866543 0.036 Uiso 1 1 calc R U . . .
C10 C 0.75163(16) 0.60465(17) 0.75388(12) 0.0310(3) Uani 1 1 d . . . . .
H10A H 0.769132 0.585406 0.685109 0.047 Uiso 1 1 calc R U . . .
H10B H 0.796931 0.535420 0.800676 0.047 Uiso 1 1 calc R U . . .
H10C H 0.791749 0.692594 0.775669 0.047 Uiso 1 1 calc R U . . .
C11 C 0.51419(17) 0.71671(13) 0.68588(11) 0.0266(3) Uani 1 1 d . . . . .
H11A H 0.538806 0.709370 0.617780 0.040 Uiso 1 1 calc R U . . .
H11B H 0.544265 0.804567 0.714871 0.040 Uiso 1 1 calc R U . . .
H11C H 0.410841 0.707120 0.681451 0.040 Uiso 1 1 calc R U . . .
C12 C 0.55959(13) 0.47655(12) 0.54298(9) 0.0162(3) Uani 1 1 d . . . . .
H12A H 0.619670 0.409397 0.515585 0.019 Uiso 1 1 calc R U . . .
H12B H 0.620814 0.554136 0.567649 0.019 Uiso 1 1 calc R U . . .
B1 B 0.42096(15) 0.28451(14) 0.60319(10) 0.0149(3) 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
F1 B1 1.3876(15) . ?
F2 B1 1.4013(16) . ?
N1 C1 1.3671(15) . ?
N1 C5 1.3810(16) . ?
N1 B1 1.5713(16) . ?
N2 C7 1.3246(16) . ?
N2 C1 1.3545(16) . ?
N3 C7 1.3451(15) . ?
N3 C12 1.4867(15) . ?
N3 B1 1.5378(16) . ?
C1 C2 1.4129(17) . ?
C2 C3 1.3674(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.4008(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3752(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.5001(17) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.5449(17) . ?
C8 C10 1.5344(19) . ?
C8 C11 1.5364(18) . ?
C8 C9 1.5395(17) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C12 1.542(2) 3_666 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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
C1 N1 C5 120.82(10) . . ?
C1 N1 B1 118.78(10) . . ?
C5 N1 B1 120.39(10) . . ?
C7 N2 C1 122.48(10) . . ?
C7 N3 C12 124.41(10) . . ?
C7 N3 B1 121.74(10) . . ?
C12 N3 B1 113.69(9) . . ?
N2 C1 N1 123.17(11) . . ?
N2 C1 C2 117.15(11) . . ?
N1 C1 C2 119.68(11) . . ?
C3 C2 C1 119.81(12) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.52(11) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.59(12) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 N1 119.57(11) . . ?
C4 C5 C6 120.79(11) . . ?
N1 C5 C6 119.64(10) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 N3 122.35(11) . . ?
N2 C7 C8 113.44(10) . . ?
N3 C7 C8 124.21(10) . . ?
C10 C8 C11 111.95(12) . . ?
C10 C8 C9 106.83(11) . . ?
C11 C8 C9 105.94(11) . . ?
C10 C8 C7 110.15(11) . . ?
C11 C8 C7 112.10(10) . . ?
C9 C8 C7 109.63(10) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C12 112.43(12) . 3_666 ?
N3 C12 H12A 109.1 . . ?
C12 C12 H12A 109.1 3_666 . ?
N3 C12 H12B 109.1 . . ?
C12 C12 H12B 109.1 3_666 . ?
H12A C12 H12B 107.8 . . ?
F1 B1 F2 110.04(10) . . ?
F1 B1 N3 109.50(10) . . ?
F2 B1 N3 110.39(10) . . ?
F1 B1 N1 108.81(10) . . ?
F2 B1 N1 108.04(10) . . ?
N3 B1 N1 110.02(10) . . ?

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
C7 N2 C1 N1 -8.42(18) . . . . ?
C7 N2 C1 C2 172.53(11) . . . . ?
C5 N1 C1 N2 -178.63(11) . . . . ?
B1 N1 C1 N2 2.48(17) . . . . ?
C5 N1 C1 C2 0.40(17) . . . . ?
B1 N1 C1 C2 -178.49(11) . . . . ?
N2 C1 C2 C3 178.37(11) . . . . ?
N1 C1 C2 C3 -0.72(18) . . . . ?
C1 C2 C3 C4 0.40(19) . . . . ?
C2 C3 C4 C5 0.24(19) . . . . ?
C3 C4 C5 N1 -0.56(18) . . . . ?
C3 C4 C5 C6 179.45(12) . . . . ?
C1 N1 C5 C4 0.24(17) . . . . ?
B1 N1 C5 C4 179.10(11) . . . . ?
C1 N1 C5 C6 -179.78(11) . . . . ?
B1 N1 C5 C6 -0.91(17) . . . . ?
C1 N2 C7 N3 2.42(18) . . . . ?
C1 N2 C7 C8 -176.75(10) . . . . ?
C12 N3 C7 N2 -166.01(11) . . . . ?
B1 N3 C7 N2 9.05(18) . . . . ?
C12 N3 C7 C8 13.07(18) . . . . ?
B1 N3 C7 C8 -171.87(11) . . . . ?
N2 C7 C8 C10 103.17(13) . . . . ?
N3 C7 C8 C10 -75.98(15) . . . . ?
N2 C7 C8 C11 -131.47(12) . . . . ?
N3 C7 C8 C11 49.38(16) . . . . ?
N2 C7 C8 C9 -14.11(14) . . . . ?
N3 C7 C8 C9 166.73(11) . . . . ?
C7 N3 C12 C12 -118.53(14) . . . 3_666 ?
B1 N3 C12 C12 66.05(16) . . . 3_666 ?
C7 N3 B1 F1 -132.62(11) . . . . ?
C12 N3 B1 F1 42.93(13) . . . . ?
C7 N3 B1 F2 106.08(12) . . . . ?
C12 N3 B1 F2 -78.36(12) . . . . ?
C7 N3 B1 N1 -13.07(15) . . . . ?
C12 N3 B1 N1 162.48(10) . . . . ?
C1 N1 B1 F1 127.32(11) . . . . ?
C5 N1 B1 F1 -51.57(15) . . . . ?
C1 N1 B1 F2 -113.23(12) . . . . ?
C5 N1 B1 F2 67.88(13) . . . . ?
C1 N1 B1 N3 7.35(15) . . . . ?
C5 N1 B1 N3 -171.54(10) . . . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 2521024'
loop_
_audit_author_name
_audit_author_address
'Colin McMillen'
;Clemson University
United States of America
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H38 B2 F4 N6'
_chemical_formula_weight         532.24

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.2300(7)
_cell_length_b                   8.6335(7)
_cell_length_c                   10.4627(8)
_cell_angle_alpha                107.216(3)
_cell_angle_beta                 105.836(3)
_cell_angle_gamma                93.887(3)
_cell_volume                     674.17(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      28.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             282
_exptl_transmission_factor_min   .
_exptl_transmission_factor_max   .
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9612
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15035
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.141
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2787
_reflns_number_gt                2438
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0404P)²+0.2813P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2787
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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
F1 F 0.58997(9) 0.10452(8) 0.83784(7) 0.01954(19) Uani 1 1 d . . . . .
F2 F 0.78337(9) 0.19054(9) 0.74324(7) 0.01972(19) Uani 1 1 d . . . . .
N1 N 0.65956(13) 0.39581(12) 0.87938(10) 0.0145(2) Uani 1 1 d . . . . .
N2 N 0.48417(12) 0.19597(12) 0.63936(10) 0.0140(2) Uani 1 1 d . . . . .
N3 N 0.44940(13) 0.47204(12) 0.71081(10) 0.0156(2) Uani 1 1 d . . . . .
C1 C 0.57300(15) 0.50957(15) 0.83663(12) 0.0147(2) Uani 1 1 d . . . . .
C2 C 0.61194(16) 0.67533(15) 0.92401(13) 0.0176(3) Uani 1 1 d . . . . .
H2 H 0.549404 0.753748 0.894531 0.021 Uiso 1 1 calc R U . . .
C3 C 0.73879(16) 0.72501(15) 1.05094(13) 0.0180(3) Uani 1 1 d . . . . .
C4 C 0.82251(16) 0.60361(16) 1.09312(13) 0.0188(3) Uani 1 1 d . . . . .
H4 H 0.909232 0.634378 1.181410 0.023 Uiso 1 1 calc R U . . .
C5 C 0.78203(15) 0.44181(15) 1.00988(12) 0.0169(3) Uani 1 1 d . . . . .
C6 C 0.78972(18) 0.90238(16) 1.14215(14) 0.0238(3) Uani 1 1 d . . . . .
H6A H 0.721602 0.969967 1.095142 0.036 Uiso 1 1 calc R U . . .
H6B H 0.911444 0.937574 1.158289 0.036 Uiso 1 1 calc R U . . .
H6C H 0.769318 0.915206 1.232455 0.036 Uiso 1 1 calc R U . . .
C7 C 0.86701(17) 0.31388(16) 1.06121(13) 0.0225(3) Uani 1 1 d . . . . .
H7A H 0.968603 0.367406 1.142258 0.034 Uiso 1 1 calc R U . . .
H7B H 0.901039 0.239210 0.985803 0.034 Uiso 1 1 calc R U . . .
H7C H 0.786940 0.251407 1.089108 0.034 Uiso 1 1 calc R U . . .
C8 C 0.40551(15) 0.32221(14) 0.61801(12) 0.0138(2) Uani 1 1 d . . . . .
C9 C 0.25463(15) 0.30772(14) 0.48670(12) 0.0153(3) Uani 1 1 d . . . . .
C10 C 0.21828(16) 0.48081(15) 0.48832(13) 0.0201(3) Uani 1 1 d . . . . .
H10A H 0.318822 0.543813 0.483564 0.030 Uiso 1 1 calc R U . . .
H10B H 0.193088 0.536947 0.575229 0.030 Uiso 1 1 calc R U . . .
H10C H 0.119810 0.471839 0.407190 0.030 Uiso 1 1 calc R U . . .
C11 C 0.09199(16) 0.21205(16) 0.49108(13) 0.0195(3) Uani 1 1 d . . . . .
H11A H 0.067002 0.267694 0.578195 0.029 Uiso 1 1 calc R U . . .
H11B H 0.110393 0.100124 0.487674 0.029 Uiso 1 1 calc R U . . .
H11C H -0.004687 0.207585 0.410145 0.029 Uiso 1 1 calc R U . . .
C12 C 0.29225(16) 0.22807(15) 0.34752(12) 0.0177(3) Uani 1 1 d . . . . .
H12A H 0.205872 0.246140 0.270169 0.027 Uiso 1 1 calc R U . . .
H12B H 0.288864 0.109803 0.330326 0.027 Uiso 1 1 calc R U . . .
H12C H 0.405956 0.277580 0.353486 0.027 Uiso 1 1 calc R U . . .
C13 C 0.43623(15) 0.02373(14) 0.54196(12) 0.0149(3) Uani 1 1 d . . . . .
H13A H 0.320457 0.009799 0.475398 0.018 Uiso 1 1 calc R U . . .
H13B H 0.431902 -0.051465 0.596781 0.018 Uiso 1 1 calc R U . . .
B1 B 0.62983(17) 0.21677(16) 0.77460(14) 0.0152(3) 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
F1 B1 1.3926(15) . ?
F2 B1 1.4060(15) . ?
N1 C1 1.3613(16) . ?
N1 C5 1.3826(15) . ?
N1 B1 1.5653(16) . ?
N2 C8 1.3482(15) . ?
N2 C13 1.4864(14) . ?
N2 B1 1.5382(16) . ?
N3 C8 1.3222(15) . ?
N3 C1 1.3582(15) . ?
C1 C2 1.4106(17) . ?
C2 C3 1.3722(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.4049(18) . ?
C3 C6 1.5037(17) . ?
C4 C5 1.3708(18) . ?
C4 H4 0.9500 . ?
C5 C7 1.4995(18) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.5464(16) . ?
C9 C10 1.5399(17) . ?
C9 C12 1.5399(16) . ?
C9 C11 1.5433(16) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C13 1.546(2) 2_656 ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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
C1 N1 C5 120.05(10) . . ?
C1 N1 B1 119.24(10) . . ?
C5 N1 B1 120.52(10) . . ?
C8 N2 C13 124.93(10) . . ?
C8 N2 B1 121.99(10) . . ?
C13 N2 B1 113.01(9) . . ?
C8 N3 C1 122.74(10) . . ?
N3 C1 N1 123.00(11) . . ?
N3 C1 C2 117.12(11) . . ?
N1 C1 C2 119.88(11) . . ?
C3 C2 C1 120.99(12) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 117.51(11) . . ?
C2 C3 C6 122.03(12) . . ?
C4 C3 C6 120.45(11) . . ?
C5 C4 C3 121.56(11) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 N1 119.90(11) . . ?
C4 C5 C7 120.26(11) . . ?
N1 C5 C7 119.82(11) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 N2 122.40(11) . . ?
N3 C8 C9 113.21(10) . . ?
N2 C8 C9 124.38(10) . . ?
C10 C9 C12 106.24(10) . . ?
C10 C9 C11 107.65(10) . . ?
C12 C9 C11 110.71(10) . . ?
C10 C9 C8 109.28(9) . . ?
C12 C9 C8 113.15(10) . . ?
C11 C9 C8 109.61(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C13 112.31(12) . 2_656 ?
N2 C13 H13A 109.1 . . ?
C13 C13 H13A 109.1 2_656 . ?
N2 C13 H13B 109.1 . . ?
C13 C13 H13B 109.1 2_656 . ?
H13A C13 H13B 107.9 . . ?
F1 B1 F2 109.12(10) . . ?
F1 B1 N2 110.00(10) . . ?
F2 B1 N2 110.14(10) . . ?
F1 B1 N1 109.75(10) . . ?
F2 B1 N1 107.50(10) . . ?
N2 B1 N1 110.28(10) . . ?

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
C8 N3 C1 N1 -1.51(18) . . . . ?
C8 N3 C1 C2 177.76(10) . . . . ?
C5 N1 C1 N3 -178.93(10) . . . . ?
B1 N1 C1 N3 6.15(17) . . . . ?
C5 N1 C1 C2 1.82(16) . . . . ?
B1 N1 C1 C2 -173.10(10) . . . . ?
N3 C1 C2 C3 -177.93(11) . . . . ?
N1 C1 C2 C3 1.36(18) . . . . ?
C1 C2 C3 C4 -2.85(17) . . . . ?
C1 C2 C3 C6 176.37(11) . . . . ?
C2 C3 C4 C5 1.27(18) . . . . ?
C6 C3 C4 C5 -177.97(11) . . . . ?
C3 C4 C5 N1 1.84(18) . . . . ?
C3 C4 C5 C7 -176.69(11) . . . . ?
C1 N1 C5 C4 -3.39(17) . . . . ?
B1 N1 C5 C4 171.46(11) . . . . ?
C1 N1 C5 C7 175.14(11) . . . . ?
B1 N1 C5 C7 -10.00(16) . . . . ?
C1 N3 C8 N2 -2.21(18) . . . . ?
C1 N3 C8 C9 176.58(10) . . . . ?
C13 N2 C8 N3 177.40(10) . . . . ?
B1 N2 C8 N3 0.76(17) . . . . ?
C13 N2 C8 C9 -1.25(17) . . . . ?
B1 N2 C8 C9 -177.89(10) . . . . ?
N3 C8 C9 C10 10.29(14) . . . . ?
N2 C8 C9 C10 -170.94(11) . . . . ?
N3 C8 C9 C12 128.44(11) . . . . ?
N2 C8 C9 C12 -52.80(15) . . . . ?
N3 C8 C9 C11 -107.46(11) . . . . ?
N2 C8 C9 C11 71.30(14) . . . . ?
C8 N2 C13 C13 104.94(15) . . . 2_656 ?
B1 N2 C13 C13 -78.15(14) . . . 2_656 ?
C8 N2 B1 F1 124.62(11) . . . . ?
C13 N2 B1 F1 -52.38(13) . . . . ?
C8 N2 B1 F2 -115.06(12) . . . . ?
C13 N2 B1 F2 67.94(12) . . . . ?
C8 N2 B1 N1 3.43(15) . . . . ?
C13 N2 B1 N1 -173.58(9) . . . . ?
C1 N1 B1 F1 -127.98(11) . . . . ?
C5 N1 B1 F1 57.12(14) . . . . ?
C1 N1 B1 F2 113.46(11) . . . . ?
C5 N1 B1 F2 -61.44(13) . . . . ?
C1 N1 B1 N2 -6.64(15) . . . . ?
C5 N1 B1 N2 178.47(9) . . . . ?

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
C13 H13A F2 0.99 2.31 2.9881(14) 124.7 2_656

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.042

