# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_mo_Werz_hk_06_069_0m_5
_database_code_depnum_ccdc_archive 'CCDC 2284407'
loop_
_audit_author_name
_audit_author_address
'Burkhard Butschke'
;Albert Ludwigs Universitaet Freiburg
Germany
;
_audit_update_record             
;
2023-07-25 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V123 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C24 H19 B F2 N2'
_chemical_formula_moiety         'C24 H19 B F2 N2'
_chemical_formula_weight         384.22
_chemical_melting_point          ?
_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                   7.0095(10)
_cell_length_b                   10.7904(16)
_cell_length_c                   12.520(3)
_cell_angle_alpha                97.995(7)
_cell_angle_beta                 93.450(7)
_cell_angle_gamma                95.353(7)
_cell_volume                     931.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5058
_cell_measurement_theta_min      2.338
_cell_measurement_theta_max      30.2895
_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_recrystallization_method 
'Crystals were obtained at room temperature by slow solvent evaporation from asolution of the compound dissolved in a mixture of pentane and dichloromethane.'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.058
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.708148
_exptl_absorpt_correction_T_max  0.74607
_exptl_absorpt_process_details   
;TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1: Krause, L., 
Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.995
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_source_current           1.4
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            5698
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_theta_min         1.647
_diffrn_reflns_theta_max         30.616
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5698
_reflns_number_gt                4725
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_computing_data_collection       
'Bruker BIS 8.5.0.27 Release/2023-03-20 && APEX4 2022.10-1'
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_solution    'SHELXT (G. Sheldrick)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+0.3243P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5698
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_twin_special_details            
'The data was integrated as a 2-component twin.'
_twin_individual_id              2
_twin_individual_twin_matrix_11  -0.0002
_twin_individual_twin_matrix_12  0.00028
_twin_individual_twin_matrix_13  1.0
_twin_individual_twin_matrix_21  -1.0
_twin_individual_twin_matrix_22  -0.00021
_twin_individual_twin_matrix_23  -0.28783
_twin_individual_twin_matrix_31  0.00025
_twin_individual_twin_matrix_32  -1.0
_twin_individual_twin_matrix_33  -0.21396

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'

_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_
_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 0.37275(14) 0.74175(8) 0.86489(7) 0.0264(2) Uani 1 1 d . . . . .
F2 F 0.04727(14) 0.71758(7) 0.83861(7) 0.02461(19) Uani 1 1 d . . . . .
N1 N 0.22293(16) 0.86698(10) 0.74609(8) 0.0148(2) Uani 1 1 d . . . . .
N2 N 0.23140(15) 0.63631(9) 0.69115(8) 0.0135(2) Uani 1 1 d . . . . .
C1 C 0.22936(19) 0.98320(12) 0.80492(10) 0.0169(2) Uani 1 1 d . . . . .
H1 H 0.235517 1.000176 0.881640 0.020 Uiso 1 1 calc R U . . .
C2 C 0.2256(2) 1.07349(12) 0.73602(10) 0.0188(2) Uani 1 1 d . . . . .
H2 H 0.228941 1.161804 0.756809 0.023 Uiso 1 1 calc R U . . .
C3 C 0.21585(19) 1.00980(12) 0.63011(10) 0.0179(2) Uani 1 1 d . . . . .
H3 H 0.210769 1.046495 0.565413 0.021 Uiso 1 1 calc R U . . .
C4 C 0.21508(18) 0.88174(11) 0.63801(10) 0.0154(2) Uani 1 1 d . . . . .
C5 C 0.21674(17) 0.77641(11) 0.55615(10) 0.0142(2) Uani 1 1 d . . . . .
C6 C 0.22461(18) 0.65654(11) 0.58215(9) 0.0139(2) Uani 1 1 d . . . . .
C7 C 0.24320(17) 0.53843(11) 0.51662(10) 0.0141(2) Uani 1 1 d . . . . .
C8 C 0.24224(19) 0.49923(12) 0.40522(10) 0.0169(2) Uani 1 1 d . . . . .
H8 H 0.224972 0.556538 0.355159 0.020 Uiso 1 1 calc R U . . .
C9 C 0.26712(19) 0.37475(13) 0.36980(10) 0.0189(2) Uani 1 1 d . . . . .
H9 H 0.266523 0.346880 0.294372 0.023 Uiso 1 1 calc R U . . .
C10 C 0.2933(2) 0.28844(12) 0.44277(11) 0.0193(2) Uani 1 1 d . . . . .
H10 H 0.311661 0.203931 0.416023 0.023 Uiso 1 1 calc R U . . .
C11 C 0.29241(19) 0.32559(12) 0.55308(10) 0.0177(2) Uani 1 1 d . . . . .
H11 H 0.308968 0.267671 0.602675 0.021 Uiso 1 1 calc R U . . .
C12 C 0.26647(18) 0.45086(11) 0.58924(10) 0.0148(2) Uani 1 1 d . . . . .
C13 C 0.25658(18) 0.51583(11) 0.69638(9) 0.0143(2) Uani 1 1 d . . . . .
C14 C 0.26802(19) 0.45837(11) 0.79639(9) 0.0154(2) Uani 1 1 d . . . . .
C15 C 0.4409(2) 0.41666(12) 0.83124(10) 0.0189(2) Uani 1 1 d . . . . .
H15 H 0.551306 0.428093 0.791865 0.023 Uiso 1 1 calc R U . . .
C16 C 0.4514(2) 0.35835(13) 0.92363(11) 0.0216(3) Uani 1 1 d . . . . .
H16 H 0.570131 0.332932 0.948822 0.026 Uiso 1 1 calc R U . . .
C17 C 0.2882(2) 0.33737(12) 0.97890(10) 0.0217(3) Uani 1 1 d . . . . .
H17 H 0.295036 0.296253 1.041161 0.026 Uiso 1 1 calc R U . . .
C18 C 0.1151(2) 0.37629(13) 0.94346(11) 0.0217(3) Uani 1 1 d . . . . .
H18 H 0.003317 0.360641 0.980794 0.026 Uiso 1 1 calc R U . . .
C19 C 0.1054(2) 0.43840(12) 0.85299(10) 0.0189(2) Uani 1 1 d . . . . .
H19 H -0.012209 0.467103 0.829956 0.023 Uiso 1 1 calc R U . . .
C20 C 0.22126(19) 0.79882(12) 0.44657(10) 0.0169(2) Uani 1 1 d . . . . .
C21 C 0.23178(19) 0.82332(12) 0.35648(10) 0.0180(2) Uani 1 1 d . . . . .
C22 C 0.2453(2) 0.84984(12) 0.24551(10) 0.0183(2) Uani 1 1 d . . . . .
H22A H 0.127643 0.810060 0.201584 0.022 Uiso 1 1 calc R U . . .
H22B H 0.355728 0.810150 0.215084 0.022 Uiso 1 1 calc R U . . .
C23 C 0.2694(2) 0.98953(12) 0.23450(10) 0.0186(2) Uani 1 1 d . . . . .
H23A H 0.164550 1.031791 0.268952 0.022 Uiso 1 1 calc R U . . .
H23B H 0.393085 1.029007 0.272012 0.022 Uiso 1 1 calc R U . . .
C24 C 0.2652(2) 1.00629(15) 0.11531(12) 0.0277(3) Uani 1 1 d . . . . .
H24A H 0.366843 0.962402 0.080898 0.042 Uiso 1 1 calc R U . . .
H24B H 0.286059 1.096058 0.109322 0.042 Uiso 1 1 calc R U . . .
H24C H 0.140047 0.971151 0.079192 0.042 Uiso 1 1 calc R U . . .
B1 B 0.2182(2) 0.74157(13) 0.79119(11) 0.0162(3) Uani 1 1 d . . . . .


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 1.3798(17) . ?
F2 B1 1.3877(17) . ?
N1 C1 1.3586(16) . ?
N1 C4 1.3828(15) . ?
N1 B1 1.5354(17) . ?
N2 C13 1.3381(15) . ?
N2 C6 1.4104(15) . ?
N2 B1 1.5827(17) . ?
C1 C2 1.3892(17) . ?
C1 H1 0.9500 . ?
C2 C3 1.4007(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3985(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.4220(17) . ?
C5 C6 1.3821(16) . ?
C5 C20 1.4275(17) . ?
C6 C7 1.4377(17) . ?
C7 C8 1.3995(17) . ?
C7 C12 1.4127(16) . ?
C8 C9 1.3850(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.4086(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3839(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3967(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.4332(17) . ?
C13 C14 1.4737(16) . ?
C14 C19 1.3934(18) . ?
C14 C15 1.3978(18) . ?
C15 C16 1.3928(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3954(17) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.1987(18) . ?
C21 C22 1.4637(17) . ?
C22 C23 1.5272(17) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5268(18) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C1 N1 C4 107.59(10) . . ?
C1 N1 B1 126.24(10) . . ?
C4 N1 B1 126.14(10) . . ?
C13 N2 C6 109.34(10) . . ?
C13 N2 B1 125.76(10) . . ?
C6 N2 B1 124.87(10) . . ?
N1 C1 C2 109.77(11) . . ?
N1 C1 H1 125.1 . . ?
C2 C1 H1 125.1 . . ?
C1 C2 C3 107.10(11) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 H2 126.5 . . ?
C4 C3 C2 106.75(11) . . ?
C4 C3 H3 126.6 . . ?
C2 C3 H3 126.6 . . ?
N1 C4 C3 108.79(11) . . ?
N1 C4 C5 120.75(11) . . ?
C3 C4 C5 130.38(11) . . ?
C6 C5 C4 121.08(11) . . ?
C6 C5 C20 120.75(11) . . ?
C4 C5 C20 118.07(11) . . ?
C5 C6 N2 120.38(11) . . ?
C5 C6 C7 131.67(11) . . ?
N2 C6 C7 107.75(10) . . ?
C8 C7 C12 119.69(11) . . ?
C8 C7 C6 134.16(11) . . ?
C12 C7 C6 106.14(10) . . ?
C9 C8 C7 118.31(11) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C10 121.67(12) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C11 C10 C9 120.62(12) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 117.96(12) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C11 C12 C7 121.73(11) . . ?
C11 C12 C13 130.81(11) . . ?
C7 C12 C13 107.45(11) . . ?
N2 C13 C12 109.29(10) . . ?
N2 C13 C14 125.33(11) . . ?
C12 C13 C14 125.36(11) . . ?
C19 C14 C15 119.62(11) . . ?
C19 C14 C13 120.63(11) . . ?
C15 C14 C13 119.64(12) . . ?
C16 C15 C14 120.08(13) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 119.97(13) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.22(12) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.99(13) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C14 C19 C18 120.07(13) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C5 176.46(14) . . ?
C20 C21 C22 178.53(14) . . ?
C21 C22 C23 114.66(11) . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C22 110.21(11) . . ?
C24 C23 H23A 109.6 . . ?
C22 C23 H23A 109.6 . . ?
C24 C23 H23B 109.6 . . ?
C22 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
F1 B1 F2 110.27(11) . . ?
F1 B1 N1 110.96(11) . . ?
F2 B1 N1 110.53(11) . . ?
F1 B1 N2 109.26(11) . . ?
F2 B1 N2 109.41(11) . . ?
N1 B1 N2 106.32(9) . . ?

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
C4 N1 C1 C2 0.06(15) . . . . ?
B1 N1 C1 C2 -178.03(12) . . . . ?
N1 C1 C2 C3 0.17(16) . . . . ?
C1 C2 C3 C4 -0.32(16) . . . . ?
C1 N1 C4 C3 -0.26(15) . . . . ?
B1 N1 C4 C3 177.83(12) . . . . ?
C1 N1 C4 C5 176.85(12) . . . . ?
B1 N1 C4 C5 -5.07(19) . . . . ?
C2 C3 C4 N1 0.36(15) . . . . ?
C2 C3 C4 C5 -176.38(13) . . . . ?
N1 C4 C5 C6 0.54(19) . . . . ?
C3 C4 C5 C6 176.94(13) . . . . ?
N1 C4 C5 C20 -175.90(12) . . . . ?
C3 C4 C5 C20 0.5(2) . . . . ?
C4 C5 C6 N2 -0.07(18) . . . . ?
C20 C5 C6 N2 176.28(11) . . . . ?
C4 C5 C6 C7 -174.28(13) . . . . ?
C20 C5 C6 C7 2.1(2) . . . . ?
C13 N2 C6 C5 -174.21(12) . . . . ?
B1 N2 C6 C5 3.90(18) . . . . ?
C13 N2 C6 C7 1.26(14) . . . . ?
B1 N2 C6 C7 179.36(11) . . . . ?
C5 C6 C7 C8 -7.0(2) . . . . ?
N2 C6 C7 C8 178.27(13) . . . . ?
C5 C6 C7 C12 173.07(13) . . . . ?
N2 C6 C7 C12 -1.69(13) . . . . ?
C12 C7 C8 C9 -0.89(18) . . . . ?
C6 C7 C8 C9 179.17(13) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 0.8(2) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C11 C12 C7 -0.52(19) . . . . ?
C10 C11 C12 C13 179.10(13) . . . . ?
C8 C7 C12 C11 1.23(19) . . . . ?
C6 C7 C12 C11 -178.81(12) . . . . ?
C8 C7 C12 C13 -178.47(11) . . . . ?
C6 C7 C12 C13 1.50(14) . . . . ?
C6 N2 C13 C12 -0.31(14) . . . . ?
B1 N2 C13 C12 -178.39(11) . . . . ?
C6 N2 C13 C14 -179.06(12) . . . . ?
B1 N2 C13 C14 2.9(2) . . . . ?
C11 C12 C13 N2 179.57(13) . . . . ?
C7 C12 C13 N2 -0.77(14) . . . . ?
C11 C12 C13 C14 -1.7(2) . . . . ?
C7 C12 C13 C14 177.98(12) . . . . ?
N2 C13 C14 C19 70.74(17) . . . . ?
C12 C13 C14 C19 -107.81(15) . . . . ?
N2 C13 C14 C15 -113.11(15) . . . . ?
C12 C13 C14 C15 68.33(17) . . . . ?
C19 C14 C15 C16 -1.63(19) . . . . ?
C13 C14 C15 C16 -177.81(12) . . . . ?
C14 C15 C16 C17 2.4(2) . . . . ?
C15 C16 C17 C18 -1.1(2) . . . . ?
C16 C17 C18 C19 -1.0(2) . . . . ?
C15 C14 C19 C18 -0.45(19) . . . . ?
C13 C14 C19 C18 175.69(12) . . . . ?
C17 C18 C19 C14 1.8(2) . . . . ?
C21 C22 C23 C24 -175.34(12) . . . . ?
C1 N1 B1 F1 -56.04(17) . . . . ?
C4 N1 B1 F1 126.23(13) . . . . ?
C1 N1 B1 F2 66.62(16) . . . . ?
C4 N1 B1 F2 -111.12(14) . . . . ?
C1 N1 B1 N2 -174.73(12) . . . . ?
C4 N1 B1 N2 7.53(17) . . . . ?
C13 N2 B1 F1 51.06(16) . . . . ?
C6 N2 B1 F1 -126.74(12) . . . . ?
C13 N2 B1 F2 -69.75(15) . . . . ?
C6 N2 B1 F2 112.45(12) . . . . ?
C13 N2 B1 N1 170.86(11) . . . . ?
C6 N2 B1 N1 -6.93(16) . . . . ?

####################################################################### 
# 
# 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_gefhalf
_database_code_depnum_ccdc_archive 'CCDC 2298672'
loop_
_audit_author_name
_audit_author_address
'Peter G. Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2023-10-02 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
_audit_creation_date             2022-05-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H15 B F2 N2'
_chemical_formula_sum            'C20 H15 B F2 N2'
_chemical_formula_weight         332.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H15 B F2 N2'
_chemical_oxdiff_usercomment     'Geffers/Werz FG6-568'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   11.2668(3)
_cell_length_b                   15.3965(4)
_cell_length_c                   9.5029(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.696(3)
_cell_angle_gamma                90
_cell_volume                     1578.97(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    29179
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.2070
_cell_measurement_theta_min      4.0720
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.931
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            64031
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        77.000
_diffrn_reflns_theta_max         77.738
_diffrn_reflns_theta_min         4.096
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  23.00   0.50    1.50    --  -48.54  64.00 118.00  174
  2  ω   -120.00 -33.00   0.50    1.50    --  -48.54 -64.00 -18.00  174
  3  ω    -22.00  64.00   0.50    1.50    --   48.54 -64.00 -18.00  172
  4  ω   -177.00 -90.00   0.50    6.00    -- -105.75 -64.00 -18.00  174
  5  ω    -78.00 -34.00   0.50    6.00    -- -105.75  64.00 118.00   88
  6  ω     90.00 178.00   0.50    6.00    --  105.75  64.00 118.00  176
  7  ω     34.00  74.00   0.50    6.00    --  105.75 -64.00 -18.00   80
  8  ω    -28.00  25.00   0.50    1.50    --  -48.54  19.00 -60.00  106
  9  ω   -120.00 -73.00   0.50    1.50    --  -48.54-125.00-120.00   94
 10  ω     74.00 121.00   0.50    1.50    --   48.54 125.00 -30.00   94
 11  ω     41.00 122.00   0.50    1.50    --   48.54  19.00 -90.00  162
 12  ω     74.00 121.00   0.50    1.50    --   48.54 125.00-150.00   94
 13  ω     33.00 121.00   0.50    1.50    --   48.54  64.00 118.00  176
 14  ω   -177.00 -85.00   0.50    6.00    -- -105.75 -77.00 -90.00  184
 15  ω   -177.00 -91.00   0.50    6.00    -- -105.75 -61.00-120.00  172
 16  ω     34.00 105.50   0.50    6.00    --  105.75-125.00 -90.00  143
 17  ω     34.00  69.00   0.50    6.00    --  105.75 -61.00  60.00   70
 18  ω     34.00 103.00   0.50    6.00    --  105.75 -77.00 -90.00  138
 19  ω     85.00 178.00   0.50    6.00    --  105.75  77.00  60.00  186
 20  ω     92.00 178.00   0.50    6.00    --  105.75  61.00-180.00  172
 21  ω     34.00 106.00   0.50    6.00    --  105.75 -94.00 -30.00  144
 22  ω     34.00  69.00   0.50    6.00    --  105.75 -61.00 120.00   70
 23  ω     92.00 178.00   0.50    6.00    --  105.75  61.00  90.00  172
 24  ω     74.00 178.00   0.50    6.00    --  105.75 125.00  90.00  208
 25  ω     98.00 178.00   0.50    6.00    --  105.75  30.00  60.00  160
 26  ω     34.00 103.00   0.50    6.00    --  105.75 -77.00  30.00  138
 27  ω     98.00 178.00   0.50    6.00    --  105.75  30.00  30.00  160
 28  ω     92.00 178.00   0.50    6.00    --  105.75  61.00 150.00  172
 29  ω     92.00 178.00   0.50    6.00    --  105.75  61.00 -90.00  172
 30  ω     85.00 178.00   0.50    6.00    --  105.75  77.00-120.00  186
 31  ω     98.00 178.00   0.50    6.00    --  105.75  30.00-180.00  160
 32  ω     34.00  69.00   0.50    6.00    --  105.75 -61.00-120.00   70
 33  ω     92.00 178.00   0.50    6.00    --  105.75  61.00-150.00  172
 34  ω     92.00 178.00   0.50    6.00    --  105.75  61.00-120.00  172
 35  ω     34.00 103.00   0.50    6.00    --  105.75 -77.00   0.00  138
 36  ω     34.00  69.00   0.50    6.00    --  105.75 -61.00-150.00   70
 37  ω     34.00  69.00   0.50    6.00    --  105.75 -61.00 150.00   70
 38  ω   -120.00 -28.00   0.50    1.50    --  -48.54 -77.00  60.00  184
 39  ω   -120.00 -28.00   0.50    1.50    --  -48.54 -77.00 -90.00  184
 40  ω   -120.00 -28.00   0.50    1.50    --  -48.54 -77.00 120.00  184
 41  ω   -120.00 -28.00   0.50    1.50    --  -48.54 -77.00-150.00  184
 42  ω   -120.00 -28.00   0.50    1.50    --  -48.54 -77.00 -30.00  184
 43  ω   -120.00 -28.00   0.50    1.50    --  -48.54 -77.00-180.00  184
 44  ω     36.00 121.00   0.50    1.50    --   48.54  57.00  30.00  170
 45  ω     41.00 121.00   0.50    1.50    --   48.54  37.00 -60.00  160
 46  ω     41.00 121.00   0.50    1.50    --   48.54  37.00   0.00  160
 47  ω    -23.00  40.00   0.50    1.50    --   48.54 -37.00-180.00  126
 48  ω   -177.00 -85.00   0.50    6.00    -- -105.75 -77.00 120.00  184
 49  ω   -177.00 -85.00   0.50    6.00    -- -105.75 -77.00 -30.00  184
 50  ω   -177.00 -85.00   0.50    6.00    -- -105.75 -77.00-150.00  184
 51  ω   -177.00 -85.00   0.50    6.00    -- -105.75 -77.00 150.00  184
 52  ω     85.00 178.00   0.50    6.00    --  105.75  77.00  30.00  186
 53  ω     92.00 178.00   0.50    6.00    --  105.75  61.00  60.00  172
 54  ω     34.00 111.00   0.50    6.00    --  105.75-125.00-180.00  154
 55  ω     92.00 178.00   0.50    6.00    --  105.75  61.00 -60.00  172
 56  ω     34.00 106.00   0.50    6.00    --  105.75 -94.00 -60.00  144
 57  ω     85.00 178.00   0.50    6.00    --  105.75  77.00 -60.00  186
 58  ω     34.00 111.00   0.50    6.00    --  105.75-125.00-150.00  154
 59  ω     85.00 178.00   0.50    6.00    --  105.75  77.00-180.00  186
 60  ω     85.00 178.00   0.50    6.00    --  105.75  77.00 120.00  186
 61  ω     85.00 178.00   0.50    6.00    --  105.75  77.00 -30.00  186
 62  ω     34.00  69.00   0.50    6.00    --  105.75 -61.00-180.00   70
 63  ω     34.00 103.00   0.50    6.00    --  105.75 -77.00  60.00  138
 64  ω     85.00 178.00   0.50    6.00    --  105.75  77.00  90.00  186
 65  ω     34.00 106.00   0.50    6.00    --  105.75 -94.00  30.00  144
 66  ω     92.00 178.00   0.50    6.00    --  105.75  61.00  30.00  172
 67  ω     34.00 100.00   0.50    6.00    --  105.75 -94.00-180.00  132
 68  ω     85.00 178.00   0.50    6.00    --  105.75  77.00   0.00  186
 69  ω     92.00 178.00   0.50    6.00    --  105.75  61.00 -30.00  172
 70  ω     85.00 178.00   0.50    6.00    --  105.75  77.00 -90.00  186
 71  ω     85.00 178.00   0.50    6.00    --  105.75  77.00 150.00  186
 72  ω     92.00 178.00   0.50    6.00    --  105.75  61.00   0.00  172
 73  ω     85.00 178.00   0.50    6.00    --  105.75  77.00-150.00  186
 74  ω     34.00  69.00   0.50    6.00    --  105.75 -61.00  90.00   70
 75  ω     34.00  99.00   0.50    6.00    --  105.75 -94.00-120.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0589644000
_diffrn_orient_matrix_UB_12      -0.0478421000
_diffrn_orient_matrix_UB_13      -0.1055624000
_diffrn_orient_matrix_UB_21      -0.1173407000
_diffrn_orient_matrix_UB_22      -0.0562502000
_diffrn_orient_matrix_UB_23      -0.0546673000
_diffrn_orient_matrix_UB_31      -0.0559753000
_diffrn_orient_matrix_UB_32      0.0675129000
_diffrn_orient_matrix_UB_33      -0.1204550000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3266
_reflns_number_total             3337
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.00086(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.153
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+0.8828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0986
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     intrinsic
_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
C1 C -0.05912(13) 0.61511(10) 0.26504(16) 0.0271(3) Uani 1 1 d . . . . .
H1A H -0.041962 0.627991 0.171790 0.041 Uiso 1 1 calc R U . . .
H1B H -0.109811 0.661684 0.288117 0.041 Uiso 1 1 calc R U . . .
H1C H -0.103876 0.559893 0.256737 0.041 Uiso 1 1 calc R U . . .
C2 C 0.05956(12) 0.60869(9) 0.38401(15) 0.0218(3) Uani 1 1 d . . . . .
C3 C 0.16958(14) 0.91567(9) 0.56327(18) 0.0282(3) Uani 1 1 d . . . . .
H3 H 0.107698 0.953696 0.506705 0.034 Uiso 1 1 calc R U . . .
C4 C 0.26922(15) 0.94074(10) 0.67861(19) 0.0305(3) Uani 1 1 d . . . . .
H4 H 0.287896 0.998090 0.715121 0.037 Uiso 1 1 calc R U . . .
C5 C 0.33756(14) 0.86571(9) 0.73165(17) 0.0255(3) Uani 1 1 d . . . . .
H5 H 0.411093 0.862384 0.811381 0.031 Uiso 1 1 calc R U . . .
C6 C 0.27705(12) 0.79666(9) 0.64501(15) 0.0209(3) Uani 1 1 d . . . . .
C7 C 0.30785(12) 0.70661(9) 0.65016(15) 0.0194(3) Uani 1 1 d . . . . .
C8 C 0.42493(12) 0.67902(9) 0.75964(15) 0.0207(3) Uani 1 1 d . . . . .
C9 C 0.53874(13) 0.70042(9) 0.73801(18) 0.0277(3) Uani 1 1 d . . . . .
H9 H 0.541295 0.730879 0.651990 0.033 Uiso 1 1 calc R U . . .
C10 C 0.64845(14) 0.67719(10) 0.8423(2) 0.0356(4) Uani 1 1 d . . . . .
H10 H 0.725940 0.691372 0.827203 0.043 Uiso 1 1 calc R U . . .
C11 C 0.64467(15) 0.63339(11) 0.96813(19) 0.0373(4) Uani 1 1 d . . . . .
H11 H 0.719661 0.618268 1.039950 0.045 Uiso 1 1 calc R U . . .
C12 C 0.53195(16) 0.61152(11) 0.98969(17) 0.0354(4) Uani 1 1 d . . . . .
H12 H 0.529878 0.580893 1.075735 0.042 Uiso 1 1 calc R U . . .
C13 C 0.42182(14) 0.63424(10) 0.88582(16) 0.0269(3) Uani 1 1 d . . . . .
H13 H 0.344601 0.619253 0.900904 0.032 Uiso 1 1 calc R U . . .
C14 C 0.23175(12) 0.64853(9) 0.55867(15) 0.0190(3) Uani 1 1 d . . . . .
C15 C 0.23941(12) 0.55543(9) 0.54013(15) 0.0195(3) Uani 1 1 d . . . . .
C16 C 0.32980(13) 0.49275(9) 0.59996(16) 0.0231(3) Uani 1 1 d . . . . .
H16 H 0.405258 0.508011 0.670829 0.028 Uiso 1 1 calc R U . . .
C17 C 0.30567(14) 0.40749(9) 0.55241(17) 0.0271(3) Uani 1 1 d . . . . .
H17 H 0.366164 0.364160 0.591576 0.033 Uiso 1 1 calc R U . . .
C18 C 0.19479(15) 0.38347(9) 0.44843(17) 0.0280(3) Uani 1 1 d . . . . .
H18 H 0.180985 0.324338 0.419866 0.034 Uiso 1 1 calc R U . . .
C19 C 0.10556(14) 0.44459(9) 0.38713(16) 0.0249(3) Uani 1 1 d . . . . .
H19 H 0.030324 0.428766 0.316378 0.030 Uiso 1 1 calc R U . . .
C20 C 0.12988(12) 0.53098(9) 0.43300(15) 0.0209(3) Uani 1 1 d . . . . .
B1 B 0.07785(14) 0.77416(10) 0.42945(18) 0.0227(3) Uani 1 1 d . . . . .
F1 F 0.07587(9) 0.79600(6) 0.28709(10) 0.0314(2) Uani 1 1 d . . . . .
F2 F -0.04002(7) 0.78528(6) 0.44572(10) 0.0293(2) Uani 1 1 d . . . . .
N1 N 0.11925(10) 0.67618(7) 0.45742(12) 0.0196(2) Uani 1 1 d . . . . .
N2 N 0.17314(11) 0.82806(7) 0.54252(14) 0.0231(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
C1 C2 1.4857(19) . ?
C2 C20 1.4367(19) . ?
C2 N1 1.3225(18) . ?
C3 C4 1.380(2) . ?
C3 N2 1.3654(19) . ?
C4 C5 1.399(2) . ?
C5 C6 1.396(2) . ?
C6 C7 1.4267(18) . ?
C6 N2 1.3776(18) . ?
C7 C8 1.4881(18) . ?
C7 C14 1.3646(19) . ?
C8 C9 1.395(2) . ?
C8 C13 1.392(2) . ?
C9 C10 1.391(2) . ?
C10 C11 1.384(3) . ?
C11 C12 1.385(3) . ?
C12 C13 1.390(2) . ?
C14 C15 1.4498(18) . ?
C14 N1 1.4188(16) . ?
C15 C16 1.3998(19) . ?
C15 C20 1.4068(19) . ?
C16 C17 1.389(2) . ?
C17 C18 1.402(2) . ?
C18 C19 1.378(2) . ?
C19 C20 1.4020(19) . ?
B1 F1 1.3880(18) . ?
B1 F2 1.3910(17) . ?
B1 N1 1.5788(19) . ?
B1 N2 1.527(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
C20 C2 C1 126.44(13) . . ?
N1 C2 C1 124.00(13) . . ?
N1 C2 C20 109.51(12) . . ?
N2 C3 C4 109.88(13) . . ?
C3 C4 C5 107.04(13) . . ?
C6 C5 C4 106.93(14) . . ?
C5 C6 C7 130.31(13) . . ?
N2 C6 C5 108.75(12) . . ?
N2 C6 C7 120.94(12) . . ?
C6 C7 C8 117.35(12) . . ?
C14 C7 C6 120.85(12) . . ?
C14 C7 C8 121.79(12) . . ?
C9 C8 C7 119.81(13) . . ?
C13 C8 C7 120.46(12) . . ?
C13 C8 C9 119.70(13) . . ?
C10 C9 C8 120.04(15) . . ?
C11 C10 C9 119.96(15) . . ?
C10 C11 C12 120.23(14) . . ?
C11 C12 C13 120.21(16) . . ?
C12 C13 C8 119.87(15) . . ?
C7 C14 C15 132.60(12) . . ?
C7 C14 N1 120.72(12) . . ?
N1 C14 C15 106.68(11) . . ?
C16 C15 C14 133.95(13) . . ?
C16 C15 C20 119.61(12) . . ?
C20 C15 C14 106.39(12) . . ?
C17 C16 C15 117.88(13) . . ?
C16 C17 C18 122.01(13) . . ?
C19 C18 C17 120.80(13) . . ?
C18 C19 C20 117.56(13) . . ?
C15 C20 C2 107.40(12) . . ?
C19 C20 C2 130.47(13) . . ?
C19 C20 C15 122.10(13) . . ?
F1 B1 F2 109.27(12) . . ?
F1 B1 N1 108.47(12) . . ?
F1 B1 N2 111.43(12) . . ?
F2 B1 N1 110.13(12) . . ?
F2 B1 N2 110.82(12) . . ?
N2 B1 N1 106.66(11) . . ?
C2 N1 C14 109.99(11) . . ?
C2 N1 B1 125.53(11) . . ?
C14 N1 B1 124.33(11) . . ?
C3 N2 C6 107.39(12) . . ?
C3 N2 B1 126.47(12) . . ?
C6 N2 B1 126.12(11) . . ?

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 C20 C15 176.03(13) . . . . ?
C1 C2 C20 C19 -1.7(2) . . . . ?
C1 C2 N1 C14 -177.41(13) . . . . ?
C1 C2 N1 B1 -1.8(2) . . . . ?
C3 C4 C5 C6 0.46(17) . . . . ?
C4 C3 N2 C6 -0.55(17) . . . . ?
C4 C3 N2 B1 177.93(13) . . . . ?
C4 C5 C6 C7 179.06(14) . . . . ?
C4 C5 C6 N2 -0.81(16) . . . . ?
C5 C6 C7 C8 -2.7(2) . . . . ?
C5 C6 C7 C14 176.72(14) . . . . ?
C5 C6 N2 C3 0.84(16) . . . . ?
C5 C6 N2 B1 -177.65(13) . . . . ?
C6 C7 C8 C9 -71.99(17) . . . . ?
C6 C7 C8 C13 106.05(15) . . . . ?
C6 C7 C14 C15 -179.99(14) . . . . ?
C6 C7 C14 N1 -0.8(2) . . . . ?
C7 C6 N2 C3 -179.04(13) . . . . ?
C7 C6 N2 B1 2.5(2) . . . . ?
C7 C8 C9 C10 177.96(13) . . . . ?
C7 C8 C13 C12 -177.75(13) . . . . ?
C7 C14 C15 C16 -5.5(3) . . . . ?
C7 C14 C15 C20 177.24(14) . . . . ?
C7 C14 N1 C2 -178.14(12) . . . . ?
C7 C14 N1 B1 6.1(2) . . . . ?
C8 C7 C14 C15 -0.6(2) . . . . ?
C8 C7 C14 N1 178.60(12) . . . . ?
C8 C9 C10 C11 -0.5(2) . . . . ?
C9 C8 C13 C12 0.3(2) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C8 0.1(2) . . . . ?
C13 C8 C9 C10 -0.1(2) . . . . ?
C14 C7 C8 C9 108.56(16) . . . . ?
C14 C7 C8 C13 -73.39(18) . . . . ?
C14 C15 C16 C17 -178.35(15) . . . . ?
C14 C15 C20 C2 2.06(15) . . . . ?
C14 C15 C20 C19 -179.94(13) . . . . ?
C15 C14 N1 C2 1.22(15) . . . . ?
C15 C14 N1 B1 -174.50(12) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C15 C20 C2 -175.65(12) . . . . ?
C16 C15 C20 C19 2.4(2) . . . . ?
C16 C17 C18 C19 1.1(2) . . . . ?
C17 C18 C19 C20 -0.2(2) . . . . ?
C18 C19 C20 C2 175.98(14) . . . . ?
C18 C19 C20 C15 -1.5(2) . . . . ?
C20 C2 N1 C14 0.07(15) . . . . ?
C20 C2 N1 B1 175.72(12) . . . . ?
C20 C15 C16 C17 -1.4(2) . . . . ?
F1 B1 N1 C2 -61.25(17) . . . . ?
F1 B1 N1 C14 113.80(14) . . . . ?
F1 B1 N2 C3 65.65(18) . . . . ?
F1 B1 N2 C6 -116.14(14) . . . . ?
F2 B1 N1 C2 58.29(18) . . . . ?
F2 B1 N1 C14 -126.66(13) . . . . ?
F2 B1 N2 C3 -56.25(18) . . . . ?
F2 B1 N2 C6 121.96(14) . . . . ?
N1 C2 C20 C15 -1.37(16) . . . . ?
N1 C2 C20 C19 -179.15(14) . . . . ?
N1 C14 C15 C16 175.21(15) . . . . ?
N1 C14 C15 C20 -2.02(14) . . . . ?
N1 B1 N2 C3 -176.13(13) . . . . ?
N1 B1 N2 C6 2.07(18) . . . . ?
N2 C3 C4 C5 0.05(17) . . . . ?
N2 C6 C7 C8 177.12(12) . . . . ?
N2 C6 C7 C14 -3.4(2) . . . . ?
N2 B1 N1 C2 178.61(12) . . . . ?
N2 B1 N1 C14 -6.33(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.269
_oxdiff_exptl_absorpt_empirical_full_min 0.836
####################################################################### 
# 
# 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_gefbrau
_database_code_depnum_ccdc_archive 'CCDC 2298673'
loop_
_audit_author_name
_audit_author_address
'Peter G. Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2023-10-02 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;
_audit_creation_date             2022-04-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 B F2 N3'
_chemical_formula_sum            'C19 H14 B F2 N3'
_chemical_formula_weight         333.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H14 B F2 N3'
_chemical_oxdiff_usercomment     'Geffers/Werz FG7-646'
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                   11.2238(3)
_cell_length_b                   15.6385(4)
_cell_length_c                   9.2476(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.535(3)
_cell_angle_gamma                90
_cell_volume                     1556.04(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    62015
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      38.2570
_cell_measurement_theta_min      2.2860
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.51a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            142487
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        36.000
_diffrn_reflns_theta_max         36.316
_diffrn_reflns_theta_min         2.298
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  96.00   0.50   20.00    --   22.89  19.00 -71.00  160
  2  ω    -49.00   5.00   0.50   20.00    --   22.89 -19.00 120.00  108
  3  ω    -31.00  50.00   0.50   20.00    --  -23.67  19.00 -71.00  162
  4  ω    -97.00 -16.00   0.50   20.00    --  -23.67 -19.00 120.00  162
  5  ω      2.00  95.00   0.50   20.00    --   22.89  77.00 -90.00  186
  6  ω      2.00  95.00   0.50   20.00    --   22.89  77.00  30.00  186
  7  ω      2.00  95.00   0.50   20.00    --   22.89  77.00-150.00  186
  8  ω    -49.00   5.00   0.50   20.00    --   22.89 -19.00  90.00  108
  9  ω     15.00  95.00   0.50   20.00    --   22.89  37.00  60.00  160
 10  ω    -59.00   2.00   0.50   20.00    --  -23.67 106.00 -53.95  122
 11  ω    -61.00  -1.00   0.50   20.00    --  -23.67 110.00-130.67  120
 12  ω    -66.00  -9.00   0.50   20.00    --  -23.67 119.00 110.02  114
 13  ω    -61.00  -1.00   0.50   20.00    --  -23.67 110.00 145.74  120
 14  ω    -59.00   2.00   0.50   20.00    --  -23.67 106.00 101.52  122
 15  ω    -64.00  -6.00   0.50   20.00    --  -23.67 115.00 -16.16  116
 16  ω    -62.00  -2.00   0.50   20.00    --  -23.67 111.00  22.41  120
 17  ω    -95.00  -3.00   0.50   20.00    --  -23.67 -77.00  90.00  184
 18  ω    -56.00  18.00   0.50   20.00    --  -23.67 101.00-150.21  148
 19  ω    -64.00  -6.00   0.50   20.00    --  -23.67 115.00-100.92  116
 20  ω    -95.00 -11.00   0.50   20.00    --  -23.67 -57.00  90.00  168
 21  ω    -49.00   5.00   0.50   20.00    --   22.89 -19.00   0.00  108
 22  ω     15.00  95.00   0.50   20.00    --   22.89  37.00-150.00  160
 23  ω     15.00  95.00   0.50   20.00    --   22.89  37.00   0.00  160
 24  ω    -64.00  -6.00   0.50   20.00    --  -23.67 116.00  53.90  116
 25  ω    -71.00 -15.00   0.50   20.00    --  -23.67 129.00 173.78  112
 26  ω    -63.00  -5.00   0.50   20.00    --  -23.67 114.00  45.23  116
 27  ω    -67.00 -10.00   0.50   20.00    --  -23.67 121.00 149.30  114
 28  ω    -65.00  -7.00   0.50   20.00    --  -23.67 117.00-122.05  116
 29  ω    -64.00  -6.00   0.50   20.00    --  -23.67 116.00 -76.30  116
 30  ω    -64.00  -6.00   0.50   20.00    --  -23.67 115.00  93.93  116
 31  ω    -72.00 -16.00   0.50   20.00    --  -23.67 130.00 -18.35  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0560615000
_diffrn_orient_matrix_UB_12      -0.0101872000
_diffrn_orient_matrix_UB_13      -0.0558546000
_diffrn_orient_matrix_UB_21      0.0333680000
_diffrn_orient_matrix_UB_22      -0.0046977000
_diffrn_orient_matrix_UB_23      -0.0541439000
_diffrn_orient_matrix_UB_31      0.0094479000
_diffrn_orient_matrix_UB_32      -0.0439428000
_diffrn_orient_matrix_UB_33      0.0187639000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6027
_reflns_number_total             7548
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.51a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    SHELXT
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         7548
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.048
_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)+(0.0811P)²+0.1936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1314
_refine_special_details          
;
The methyl hydrogen atoms at C1 were indistinct. This group was therefore 
refined as a rigid group using a regular hexagon of half-occupied 
hydrogen positions (AFIX 127).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) H1D(0.5) H1E(0.5) H1F(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18)
3.b Disordered Me refined as rotating group:
 C1(H1A,H1B,H1C,H1D,H1E,H1F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     intrinsic
_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
C1 C -0.06108(7) 0.60296(6) 0.23825(9) 0.02476(15) Uani 1 1 d . . . . .
H1A H -0.104278 0.657014 0.241957 0.037 Uiso 0.5 1 calc R U P . .
H1B H -0.113844 0.555128 0.250359 0.037 Uiso 0.5 1 calc R U P . .
H1C H -0.043167 0.597998 0.140871 0.037 Uiso 0.5 1 calc R U P . .
H1D H -0.069914 0.549746 0.180168 0.037 Uiso 0.5 1 calc R U P . .
H1E H -0.060349 0.651633 0.171766 0.037 Uiso 0.5 1 calc R U P . .
H1F H -0.131025 0.608762 0.281254 0.037 Uiso 0.5 1 calc R U P . .
C2 C 0.05683(6) 0.60103(4) 0.36147(8) 0.01832(12) Uani 1 1 d . . . . .
C3 C 0.24309(8) 0.93207(5) 0.63491(10) 0.02549(15) Uani 1 1 d . . . . .
H3 H 0.256916 0.989941 0.666442 0.031 Uiso 1 1 calc R U . . .
C4 C 0.32027(7) 0.86393(5) 0.70276(9) 0.02172(13) Uani 1 1 d . . . . .
H4 H 0.393178 0.865948 0.785791 0.026 Uiso 1 1 calc R U . . .
C5 C 0.26516(6) 0.79268(4) 0.62013(8) 0.01716(11) Uani 1 1 d . . . . .
C6 C 0.30040(6) 0.70367(4) 0.63215(7) 0.01485(11) Uani 1 1 d . . . . .
C7 C 0.41764(6) 0.67911(4) 0.74583(8) 0.01713(12) Uani 1 1 d . . . . .
C8 C 0.53176(7) 0.70408(5) 0.72697(11) 0.02614(15) Uani 1 1 d . . . . .
H8 H 0.534161 0.736781 0.641271 0.031 Uiso 1 1 calc R U . . .
C9 C 0.64221(8) 0.68104(6) 0.83384(13) 0.0357(2) Uani 1 1 d . . . . .
H9 H 0.719830 0.697505 0.820377 0.043 Uiso 1 1 calc R U . . .
C10 C 0.63862(9) 0.63423(7) 0.95940(12) 0.0380(2) Uani 1 1 d . . . . .
H10 H 0.713866 0.618907 1.032478 0.046 Uiso 1 1 calc R U . . .
C11 C 0.52525(9) 0.60952(7) 0.97902(10) 0.0333(2) Uani 1 1 d . . . . .
H11 H 0.523271 0.577364 1.065470 0.040 Uiso 1 1 calc R U . . .
C12 C 0.41474(8) 0.63172(5) 0.87251(8) 0.02348(14) Uani 1 1 d . . . . .
H12 H 0.337393 0.614616 0.886015 0.028 Uiso 1 1 calc R U . . .
C13 C 0.22628(6) 0.64458(4) 0.54136(7) 0.01485(11) Uani 1 1 d . . . . .
C14 C 0.23751(6) 0.55239(4) 0.52805(7) 0.01591(11) Uani 1 1 d . . . . .
C15 C 0.32900(7) 0.49229(4) 0.59461(8) 0.01967(12) Uani 1 1 d . . . . .
H15 H 0.403859 0.509066 0.666962 0.024 Uiso 1 1 calc R U . . .
C16 C 0.30688(8) 0.40703(5) 0.55148(10) 0.02467(15) Uani 1 1 d . . . . .
H16 H 0.368074 0.365380 0.595495 0.030 Uiso 1 1 calc R U . . .
C17 C 0.19692(8) 0.38086(5) 0.44496(10) 0.02604(15) Uani 1 1 d . . . . .
H17 H 0.183822 0.321965 0.420405 0.031 Uiso 1 1 calc R U . . .
C18 C 0.10723(7) 0.44025(5) 0.37527(9) 0.02336(14) Uani 1 1 d . . . . .
H18 H 0.033395 0.423413 0.301162 0.028 Uiso 1 1 calc R U . . .
C19 C 0.12945(6) 0.52567(4) 0.41805(8) 0.01798(12) Uani 1 1 d . . . . .
B1 B 0.06671(7) 0.76477(5) 0.39954(9) 0.01852(13) Uani 1 1 d . . . . .
F1 F 0.06459(5) 0.78416(3) 0.25259(5) 0.02499(11) Uani 1 1 d . . . . .
F2 F -0.05099(4) 0.77333(3) 0.41724(6) 0.02425(11) Uani 1 1 d . . . . .
N1 N 0.11360(5) 0.66926(4) 0.43434(7) 0.01649(10) Uani 1 1 d . . . . .
N2 N 0.16192(6) 0.81986(4) 0.51279(7) 0.01878(11) Uani 1 1 d . . . . .
N3 N 0.14753(7) 0.90569(4) 0.52028(9) 0.02438(13) 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
C1 C2 1.4807(9) . ?
C2 C19 1.4437(10) . ?
C2 N1 1.3245(9) . ?
C3 C4 1.4037(11) . ?
C3 N3 1.3406(12) . ?
C4 C5 1.3925(10) . ?
C5 C6 1.4427(9) . ?
C5 N2 1.3616(9) . ?
C6 C7 1.4821(9) . ?
C6 C13 1.3614(9) . ?
C7 C8 1.3966(11) . ?
C7 C12 1.3944(11) . ?
C8 C9 1.3950(12) . ?
C9 C10 1.3829(18) . ?
C10 C11 1.3903(17) . ?
C11 C12 1.3906(11) . ?
C13 C14 1.4555(9) . ?
C13 N1 1.4197(8) . ?
C14 C15 1.3989(9) . ?
C14 C19 1.4065(9) . ?
C15 C16 1.3936(10) . ?
C16 C17 1.4032(11) . ?
C17 C18 1.3863(12) . ?
C18 C19 1.3954(10) . ?
B1 F1 1.3860(9) . ?
B1 F2 1.3832(9) . ?
B1 N1 1.5858(10) . ?
B1 N2 1.5310(10) . ?
N2 N3 1.3560(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 C2 C1 125.75(6) . . ?
N1 C2 C1 124.77(6) . . ?
N1 C2 C19 109.45(6) . . ?
N3 C3 C4 111.90(7) . . ?
C5 C4 C3 103.94(7) . . ?
C4 C5 C6 131.34(7) . . ?
N2 C5 C4 107.65(6) . . ?
N2 C5 C6 121.01(6) . . ?
C5 C6 C7 118.24(6) . . ?
C13 C6 C5 120.09(6) . . ?
C13 C6 C7 121.67(6) . . ?
C8 C7 C6 119.98(7) . . ?
C12 C7 C6 120.35(6) . . ?
C12 C7 C8 119.67(7) . . ?
C9 C8 C7 120.07(9) . . ?
C10 C9 C8 119.95(9) . . ?
C9 C10 C11 120.21(8) . . ?
C10 C11 C12 120.21(9) . . ?
C11 C12 C7 119.89(8) . . ?
C6 C13 C14 132.22(6) . . ?
C6 C13 N1 120.81(6) . . ?
N1 C13 C14 106.97(5) . . ?
C15 C14 C13 134.33(6) . . ?
C15 C14 C19 119.51(6) . . ?
C19 C14 C13 106.13(5) . . ?
C16 C15 C14 117.92(7) . . ?
C15 C16 C17 121.96(7) . . ?
C18 C17 C16 120.54(7) . . ?
C17 C18 C19 117.52(7) . . ?
C14 C19 C2 107.54(6) . . ?
C18 C19 C2 129.93(6) . . ?
C18 C19 C14 122.49(6) . . ?
F1 B1 N1 108.49(6) . . ?
F1 B1 N2 111.19(6) . . ?
F2 B1 F1 110.14(6) . . ?
F2 B1 N1 109.89(6) . . ?
F2 B1 N2 111.64(6) . . ?
N2 B1 N1 105.33(5) . . ?
C2 N1 C13 109.86(6) . . ?
C2 N1 B1 124.87(6) . . ?
C13 N1 B1 125.16(6) . . ?
C5 N2 B1 127.34(6) . . ?
N3 N2 C5 111.15(6) . . ?
N3 N2 B1 121.45(6) . . ?
C3 N3 N2 105.36(6) . . ?

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 C19 C14 176.53(7) . . . . ?
C1 C2 C19 C18 -1.17(13) . . . . ?
C1 C2 N1 C13 -177.88(7) . . . . ?
C1 C2 N1 B1 -1.51(11) . . . . ?
C3 C4 C5 C6 179.02(8) . . . . ?
C3 C4 C5 N2 -0.56(8) . . . . ?
C4 C3 N3 N2 0.02(9) . . . . ?
C4 C5 C6 C7 -2.92(12) . . . . ?
C4 C5 C6 C13 176.57(7) . . . . ?
C4 C5 N2 B1 -176.62(7) . . . . ?
C4 C5 N2 N3 0.62(8) . . . . ?
C5 C6 C7 C8 -68.90(9) . . . . ?
C5 C6 C7 C12 110.57(8) . . . . ?
C5 C6 C13 C14 179.93(7) . . . . ?
C5 C6 C13 N1 -0.21(10) . . . . ?
C5 N2 N3 C3 -0.40(9) . . . . ?
C6 C5 N2 B1 3.76(11) . . . . ?
C6 C5 N2 N3 -179.01(6) . . . . ?
C6 C7 C8 C9 179.99(7) . . . . ?
C6 C7 C12 C11 -179.56(7) . . . . ?
C6 C13 C14 C15 -4.51(14) . . . . ?
C6 C13 C14 C19 177.82(7) . . . . ?
C6 C13 N1 C2 -178.94(6) . . . . ?
C6 C13 N1 B1 4.70(10) . . . . ?
C7 C6 C13 C14 -0.60(12) . . . . ?
C7 C6 C13 N1 179.27(6) . . . . ?
C7 C8 C9 C10 -0.70(13) . . . . ?
C8 C7 C12 C11 -0.08(11) . . . . ?
C8 C9 C10 C11 0.43(14) . . . . ?
C9 C10 C11 C12 0.00(14) . . . . ?
C10 C11 C12 C7 -0.18(13) . . . . ?
C12 C7 C8 C9 0.52(12) . . . . ?
C13 C6 C7 C8 111.62(8) . . . . ?
C13 C6 C7 C12 -68.91(9) . . . . ?
C13 C14 C15 C16 -179.32(8) . . . . ?
C13 C14 C19 C2 2.36(8) . . . . ?
C13 C14 C19 C18 -179.73(7) . . . . ?
C14 C13 N1 C2 0.95(8) . . . . ?
C14 C13 N1 B1 -175.40(6) . . . . ?
C14 C15 C16 C17 -0.07(12) . . . . ?
C15 C14 C19 C2 -175.73(7) . . . . ?
C15 C14 C19 C18 2.18(11) . . . . ?
C15 C16 C17 C18 1.87(13) . . . . ?
C16 C17 C18 C19 -1.60(13) . . . . ?
C17 C18 C19 C2 177.01(8) . . . . ?
C17 C18 C19 C14 -0.39(12) . . . . ?
C19 C2 N1 C13 0.53(8) . . . . ?
C19 C2 N1 B1 176.90(6) . . . . ?
C19 C14 C15 C16 -1.89(11) . . . . ?
B1 N2 N3 C3 177.02(7) . . . . ?
F1 B1 N1 C2 -61.15(9) . . . . ?
F1 B1 N1 C13 114.67(7) . . . . ?
F1 B1 N2 C5 -117.08(8) . . . . ?
F1 B1 N2 N3 65.95(9) . . . . ?
F2 B1 N1 C2 59.33(9) . . . . ?
F2 B1 N1 C13 -124.85(7) . . . . ?
F2 B1 N2 C5 119.47(8) . . . . ?
F2 B1 N2 N3 -57.50(9) . . . . ?
N1 C2 C19 C14 -1.86(8) . . . . ?
N1 C2 C19 C18 -179.57(8) . . . . ?
N1 C13 C14 C15 175.62(8) . . . . ?
N1 C13 C14 C19 -2.06(7) . . . . ?
N1 B1 N2 C5 0.25(10) . . . . ?
N1 B1 N2 N3 -176.73(6) . . . . ?
N2 C5 C6 C7 176.61(6) . . . . ?
N2 C5 C6 C13 -3.90(10) . . . . ?
N2 B1 N1 C2 179.71(7) . . . . ?
N2 B1 N1 C13 -4.47(9) . . . . ?
N3 C3 C4 C5 0.34(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.858
####################################################################### 
# 
# 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_zwitgef
_database_code_depnum_ccdc_archive 'CCDC 2298671'
loop_
_audit_author_name
_audit_author_address
'Peter G. Jones'
;TU Braunschweig
Germany
;
_audit_update_record             
;
2023-10-02 deposited with the CCDC.	2023-11-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 B F2 N2'
_chemical_formula_weight         394.21

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/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                   11.1893(2)
_cell_length_b                   10.9459(2)
_cell_length_c                   15.6815(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.820(2)
_cell_angle_gamma                90
_cell_volume                     1918.29(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    87640
_cell_measurement_theta_min      2.2610
_cell_measurement_theta_max      35.8770

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.80917
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            149697
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.270
_diffrn_reflns_theta_max         35.949
_diffrn_reflns_theta_full        35.000
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             8633
_reflns_number_gt                7432
_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       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0608P)²+0.6260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         8633
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
N1 N 0.65540(5) 0.37306(6) 0.35582(4) 0.01308(10) Uani 1 1 d . . . . .
N2 N 0.65247(6) 0.46812(6) 0.21095(4) 0.01486(11) Uani 1 1 d . . . . .
C1 C 0.69445(6) 0.33449(7) 0.43330(4) 0.01376(11) Uani 1 1 d . . . . .
C2 C 0.81908(6) 0.30143(7) 0.45816(5) 0.01606(12) Uani 1 1 d . . . . .
C3 C 0.87037(8) 0.19812(9) 0.42295(6) 0.02408(16) Uani 1 1 d . . . . .
H3 H 0.827628 0.153633 0.379286 0.029 Uiso 1 1 calc R U . . .
C4 C 0.98390(9) 0.16003(10) 0.45157(7) 0.0303(2) Uani 1 1 d . . . . .
H4 H 1.018084 0.088937 0.427988 0.036 Uiso 1 1 calc R U . . .
C5 C 1.04753(8) 0.22578(11) 0.51465(7) 0.0312(2) Uani 1 1 d . . . . .
H5 H 1.125360 0.200055 0.533839 0.037 Uiso 1 1 calc R U . . .
C6 C 0.99717(10) 0.32882(12) 0.54943(8) 0.0363(2) Uani 1 1 d . . . . .
H6 H 1.040929 0.374304 0.592068 0.044 Uiso 1 1 calc R U . . .
C7 C 0.88257(8) 0.36598(10) 0.52208(7) 0.02852(19) Uani 1 1 d . . . . .
H7 H 0.847619 0.435578 0.547117 0.034 Uiso 1 1 calc R U . . .
C8 C 0.59534(6) 0.32466(7) 0.48722(4) 0.01382(11) Uani 1 1 d . . . . .
C9 C 0.59236(7) 0.29297(7) 0.57381(5) 0.01717(13) Uani 1 1 d . . . . .
H9 H 0.662697 0.268352 0.605641 0.021 Uiso 1 1 calc R U . . .
C10 C 0.48292(8) 0.29901(7) 0.61095(5) 0.01871(14) Uani 1 1 d . . . . .
H10 H 0.477977 0.279654 0.669728 0.022 Uiso 1 1 calc R U . . .
C11 C 0.37870(7) 0.33346(7) 0.56286(5) 0.01790(13) Uani 1 1 d . . . . .
H11 H 0.304992 0.337894 0.590294 0.021 Uiso 1 1 calc R U . . .
C12 C 0.38060(7) 0.36113(7) 0.47645(5) 0.01588(12) Uani 1 1 d . . . . .
H12 H 0.309312 0.382485 0.444507 0.019 Uiso 1 1 calc R U . . .
C13 C 0.49107(6) 0.35659(6) 0.43777(4) 0.01319(11) Uani 1 1 d . . . . .
C14 C 0.52985(6) 0.38600(6) 0.35363(4) 0.01266(11) Uani 1 1 d . . . . .
C15 C 0.46757(6) 0.42870(6) 0.28164(4) 0.01286(11) Uani 1 1 d . . . . .
C16 C 0.52903(6) 0.47397(7) 0.21111(4) 0.01397(11) Uani 1 1 d . . . . .
C17 C 0.48620(7) 0.52538(7) 0.13334(5) 0.01708(13) Uani 1 1 d . . . . .
H17 H 0.404893 0.540294 0.116209 0.021 Uiso 1 1 calc R U . . .
C18 C 0.58627(8) 0.55044(8) 0.08585(5) 0.01912(14) Uani 1 1 d . . . . .
H18 H 0.585701 0.586318 0.030672 0.023 Uiso 1 1 calc R U . . .
C19 C 0.68639(7) 0.51286(8) 0.13482(5) 0.01840(13) Uani 1 1 d . . . . .
H19 H 0.766552 0.517664 0.117752 0.022 Uiso 1 1 calc R U . . .
C20 C 0.33519(6) 0.41978(7) 0.27547(4) 0.01394(12) Uani 1 1 d . . . . .
C21 C 0.26190(7) 0.52253(8) 0.26673(5) 0.01830(13) Uani 1 1 d . . . . .
H21 H 0.296335 0.601646 0.263650 0.022 Uiso 1 1 calc R U . . .
C22 C 0.13769(8) 0.50864(9) 0.26252(6) 0.02396(16) Uani 1 1 d . . . . .
H22 H 0.087723 0.578783 0.258491 0.029 Uiso 1 1 calc R U . . .
C23 C 0.08663(7) 0.39306(10) 0.26419(6) 0.02643(17) Uani 1 1 d . . . . .
H23 H 0.002077 0.384178 0.260804 0.032 Uiso 1 1 calc R U . . .
C24 C 0.15970(7) 0.29036(9) 0.27082(6) 0.02324(16) Uani 1 1 d . . . . .
H24 H 0.125042 0.211128 0.270925 0.028 Uiso 1 1 calc R U . . .
C25 C 0.28330(7) 0.30352(7) 0.27729(5) 0.01733(13) Uani 1 1 d . . . . .
H25 H 0.332867 0.233239 0.282981 0.021 Uiso 1 1 calc R U . . .
B1 B 0.73590(7) 0.41071(8) 0.28034(5) 0.01405(13) Uani 1 1 d . . . . .
F1 F 0.79192(4) 0.30820(5) 0.24823(3) 0.01882(10) Uani 1 1 d . . . . .
F2 F 0.82094(4) 0.49465(5) 0.31041(3) 0.01895(10) 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
N1 C1 1.3391(9) . ?
N1 C14 1.4107(9) . ?
N1 B1 1.5770(10) . ?
N2 C19 1.3614(10) . ?
N2 C16 1.3828(9) . ?
N2 B1 1.5332(10) . ?
C1 C8 1.4313(10) . ?
C1 C2 1.4745(10) . ?
C2 C7 1.3924(11) . ?
C2 C3 1.3944(11) . ?
C3 C4 1.3902(12) . ?
C4 C5 1.3907(15) . ?
C5 C6 1.3846(16) . ?
C6 C7 1.3926(13) . ?
C8 C9 1.4034(10) . ?
C8 C13 1.4127(10) . ?
C9 C10 1.3832(11) . ?
C10 C11 1.4086(12) . ?
C11 C12 1.3898(11) . ?
C12 C13 1.4043(10) . ?
C13 C14 1.4454(10) . ?
C14 C15 1.3788(9) . ?
C15 C16 1.4202(10) . ?
C15 C20 1.4828(10) . ?
C16 C17 1.4057(10) . ?
C17 C18 1.4019(11) . ?
C18 C19 1.3891(12) . ?
C20 C21 1.3947(10) . ?
C20 C25 1.3997(11) . ?
C21 C22 1.3965(11) . ?
C22 C23 1.3889(14) . ?
C23 C24 1.3909(13) . ?
C24 C25 1.3893(11) . ?
B1 F2 1.3885(9) . ?
B1 F1 1.3916(9) . ?

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 C14 109.50(6) . . ?
C1 N1 B1 126.19(6) . . ?
C14 N1 B1 124.09(6) . . ?
C19 N2 C16 107.85(6) . . ?
C19 N2 B1 125.70(6) . . ?
C16 N2 B1 126.23(6) . . ?
N1 C1 C8 109.39(6) . . ?
N1 C1 C2 125.41(6) . . ?
C8 C1 C2 125.14(6) . . ?
C7 C2 C3 119.42(7) . . ?
C7 C2 C1 120.55(7) . . ?
C3 C2 C1 119.78(7) . . ?
C4 C3 C2 120.18(8) . . ?
C3 C4 C5 120.14(9) . . ?
C6 C5 C4 119.85(8) . . ?
C5 C6 C7 120.20(9) . . ?
C2 C7 C6 120.19(9) . . ?
C9 C8 C13 122.27(7) . . ?
C9 C8 C1 130.25(7) . . ?
C13 C8 C1 107.46(6) . . ?
C10 C9 C8 117.34(7) . . ?
C9 C10 C11 120.94(7) . . ?
C12 C11 C10 121.90(7) . . ?
C11 C12 C13 118.00(7) . . ?
C12 C13 C8 119.50(6) . . ?
C12 C13 C14 134.15(7) . . ?
C8 C13 C14 106.21(6) . . ?
C15 C14 N1 121.10(6) . . ?
C15 C14 C13 131.34(6) . . ?
N1 C14 C13 107.38(6) . . ?
C14 C15 C16 120.76(6) . . ?
C14 C15 C20 119.61(6) . . ?
C16 C15 C20 119.51(6) . . ?
N2 C16 C17 108.36(6) . . ?
N2 C16 C15 120.48(6) . . ?
C17 C16 C15 131.14(7) . . ?
C18 C17 C16 106.98(7) . . ?
C19 C18 C17 106.97(7) . . ?
N2 C19 C18 109.83(7) . . ?
C21 C20 C25 119.52(7) . . ?
C21 C20 C15 122.28(7) . . ?
C25 C20 C15 118.20(6) . . ?
C20 C21 C22 119.73(8) . . ?
C23 C22 C21 120.50(8) . . ?
C22 C23 C24 119.79(8) . . ?
C25 C24 C23 120.06(8) . . ?
C24 C25 C20 120.35(7) . . ?
F2 B1 F1 110.07(6) . . ?
F2 B1 N2 110.66(6) . . ?
F1 B1 N2 110.06(6) . . ?
F2 B1 N1 108.98(6) . . ?
F1 B1 N1 110.18(6) . . ?
N2 B1 N1 106.83(6) . . ?

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
C14 N1 C1 C8 -2.20(8) . . . . ?
B1 N1 C1 C8 172.48(6) . . . . ?
C14 N1 C1 C2 175.04(7) . . . . ?
B1 N1 C1 C2 -10.28(12) . . . . ?
N1 C1 C2 C7 118.12(10) . . . . ?
C8 C1 C2 C7 -65.06(11) . . . . ?
N1 C1 C2 C3 -67.64(11) . . . . ?
C8 C1 C2 C3 109.17(9) . . . . ?
C7 C2 C3 C4 0.05(15) . . . . ?
C1 C2 C3 C4 -174.25(9) . . . . ?
C2 C3 C4 C5 -0.88(17) . . . . ?
C3 C4 C5 C6 0.51(18) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C3 C2 C7 C6 1.16(16) . . . . ?
C1 C2 C7 C6 175.42(10) . . . . ?
C5 C6 C7 C2 -1.54(19) . . . . ?
N1 C1 C8 C9 -177.15(8) . . . . ?
C2 C1 C8 C9 5.60(13) . . . . ?
N1 C1 C8 C13 1.49(8) . . . . ?
C2 C1 C8 C13 -175.76(7) . . . . ?
C13 C8 C9 C10 -2.70(11) . . . . ?
C1 C8 C9 C10 175.76(8) . . . . ?
C8 C9 C10 C11 1.17(11) . . . . ?
C9 C10 C11 C12 0.87(12) . . . . ?
C10 C11 C12 C13 -1.41(11) . . . . ?
C11 C12 C13 C8 -0.09(11) . . . . ?
C11 C12 C13 C14 -175.24(8) . . . . ?
C9 C8 C13 C12 2.19(11) . . . . ?
C1 C8 C13 C12 -176.58(7) . . . . ?
C9 C8 C13 C14 178.57(7) . . . . ?
C1 C8 C13 C14 -0.20(8) . . . . ?
C1 N1 C14 C15 177.79(7) . . . . ?
B1 N1 C14 C15 2.97(11) . . . . ?
C1 N1 C14 C13 2.05(8) . . . . ?
B1 N1 C14 C13 -172.77(6) . . . . ?
C12 C13 C14 C15 -0.61(14) . . . . ?
C8 C13 C14 C15 -176.21(8) . . . . ?
C12 C13 C14 N1 174.53(8) . . . . ?
C8 C13 C14 N1 -1.08(8) . . . . ?
N1 C14 C15 C16 -7.22(11) . . . . ?
C13 C14 C15 C16 167.35(7) . . . . ?
N1 C14 C15 C20 168.75(6) . . . . ?
C13 C14 C15 C20 -16.68(12) . . . . ?
C19 N2 C16 C17 -0.84(9) . . . . ?
B1 N2 C16 C17 -175.66(7) . . . . ?
C19 N2 C16 C15 177.52(7) . . . . ?
B1 N2 C16 C15 2.70(11) . . . . ?
C14 C15 C16 N2 4.55(11) . . . . ?
C20 C15 C16 N2 -171.42(7) . . . . ?
C14 C15 C16 C17 -177.50(8) . . . . ?
C20 C15 C16 C17 6.52(12) . . . . ?
N2 C16 C17 C18 0.10(9) . . . . ?
C15 C16 C17 C18 -178.03(8) . . . . ?
C16 C17 C18 C19 0.67(9) . . . . ?
C16 N2 C19 C18 1.29(9) . . . . ?
B1 N2 C19 C18 176.14(7) . . . . ?
C17 C18 C19 N2 -1.22(9) . . . . ?
C14 C15 C20 C21 119.41(8) . . . . ?
C16 C15 C20 C21 -64.57(10) . . . . ?
C14 C15 C20 C25 -61.55(9) . . . . ?
C16 C15 C20 C25 114.47(8) . . . . ?
C25 C20 C21 C22 1.95(11) . . . . ?
C15 C20 C21 C22 -179.03(7) . . . . ?
C20 C21 C22 C23 -2.10(13) . . . . ?
C21 C22 C23 C24 0.55(14) . . . . ?
C22 C23 C24 C25 1.14(14) . . . . ?
C23 C24 C25 C20 -1.28(13) . . . . ?
C21 C20 C25 C24 -0.27(12) . . . . ?
C15 C20 C25 C24 -179.34(7) . . . . ?
C19 N2 B1 F2 61.53(10) . . . . ?
C16 N2 B1 F2 -124.55(8) . . . . ?
C19 N2 B1 F1 -60.35(9) . . . . ?
C16 N2 B1 F1 113.57(8) . . . . ?
C19 N2 B1 N1 -179.96(7) . . . . ?
C16 N2 B1 N1 -6.04(10) . . . . ?
C1 N1 B1 F2 -51.12(10) . . . . ?
C14 N1 B1 F2 122.83(7) . . . . ?
C1 N1 B1 F1 69.74(9) . . . . ?
C14 N1 B1 F1 -116.31(7) . . . . ?
C1 N1 B1 N2 -170.72(7) . . . . ?
C14 N1 B1 N2 3.23(9) . . . . ?

_refine_diff_density_max         0.534
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.056



