# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
# 
#######################################################################

data_LP18026_xprep_a
_database_code_depnum_ccdc_archive 'CCDC 2209988'
loop_
_audit_author_name
_audit_author_address
'Lukas Pfeifer'
;Ecole Polytechnique Federale de Lausanne
Switzerland
;
_audit_update_record             
;
2022-09-28 deposited with the CCDC.	2022-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 B F2 N3'
_chemical_formula_weight         319.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 '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'

_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                   9.1067(3)
_cell_length_b                   12.5882(4)
_cell_length_c                   12.6809(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.1690(10)
_cell_angle_gamma                90
_cell_volume                     1438.95(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9884
_cell_measurement_theta_min      4.98
_cell_measurement_theta_max      74.57

_exptl_crystal_description       block
_exptl_crystal_colour            lustrous_dark_red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.885
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6947
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27803
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.975
_diffrn_reflns_theta_max         74.470
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2944
_reflns_number_gt                2690
_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 V2016.1-0'
_computing_cell_refinement       'Bruker SAINT 8.37A'
_computing_data_reduction        'Bruker SAINT 8.37A'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0358P)²+0.6481P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2944
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.09856(7) 0.36649(5) 0.41362(5) 0.01953(16) Uani 1 1 d . . . . .
F2 F 0.20848(8) 0.45313(5) 0.56105(5) 0.02103(16) Uani 1 1 d . . . . .
N1 N 0.37242(10) 0.37001(7) 0.44484(7) 0.01420(19) Uani 1 1 d . . . . .
N2 N 0.45223(10) 0.42663(7) 0.37896(7) 0.0171(2) Uani 1 1 d . . . . .
N3 N 0.24048(10) 0.52383(7) 0.38659(7) 0.0154(2) Uani 1 1 d . . . . .
C1 C 0.42922(12) 0.28224(9) 0.48920(8) 0.0151(2) Uani 1 1 d . . . . .
C2 C 0.35925(13) 0.21084(9) 0.56016(8) 0.0172(2) Uani 1 1 d . . . . .
C3 C 0.22069(13) 0.21021(10) 0.59468(9) 0.0212(2) Uani 1 1 d . . . . .
H3 H 0.148742 0.262813 0.570911 0.025 Uiso 1 1 calc R U . . .
C4 C 0.18992(15) 0.13058(10) 0.66497(9) 0.0256(3) Uani 1 1 d . . . . .
H4 H 0.095844 0.129351 0.689110 0.031 Uiso 1 1 calc R U . . .
C5 C 0.29374(16) 0.05326(10) 0.70027(9) 0.0279(3) Uani 1 1 d . . . . .
H5 H 0.271096 0.000989 0.749538 0.033 Uiso 1 1 calc R U . . .
C6 C 0.43051(15) 0.05173(10) 0.66409(9) 0.0253(3) Uani 1 1 d . . . . .
H6 H 0.500993 -0.002118 0.686913 0.030 Uiso 1 1 calc R U . . .
C7 C 0.46251(13) 0.13005(9) 0.59416(9) 0.0191(2) Uani 1 1 d . . . . .
C8 C 0.59598(13) 0.14604(9) 0.54378(9) 0.0192(2) Uani 1 1 d . . . . .
C9 C 0.72572(14) 0.08771(10) 0.55187(10) 0.0254(3) Uani 1 1 d . . . . .
H9 H 0.738893 0.026227 0.595645 0.031 Uiso 1 1 calc R U . . .
C10 C 0.83660(14) 0.12115(10) 0.49439(11) 0.0282(3) Uani 1 1 d . . . . .
H10 H 0.926004 0.081524 0.498450 0.034 Uiso 1 1 calc R U . . .
C11 C 0.81845(13) 0.21154(10) 0.43123(10) 0.0252(3) Uani 1 1 d . . . . .
H11 H 0.895681 0.232793 0.392713 0.030 Uiso 1 1 calc R U . . .
C12 C 0.68854(12) 0.27183(9) 0.42334(9) 0.0195(2) Uani 1 1 d . . . . .
H12 H 0.677037 0.334230 0.380827 0.023 Uiso 1 1 calc R U . . .
C13 C 0.57642(12) 0.23795(9) 0.47946(9) 0.0165(2) Uani 1 1 d . . . . .
C14 C 0.37204(12) 0.51362(9) 0.34831(8) 0.0159(2) Uani 1 1 d . . . . .
C15 C 0.41443(13) 0.59270(9) 0.27937(9) 0.0203(2) Uani 1 1 d . . . . .
H15 H 0.506946 0.588437 0.253185 0.024 Uiso 1 1 calc R U . . .
C16 C 0.31963(14) 0.67544(9) 0.25114(9) 0.0222(3) Uani 1 1 d . . . . .
H16 H 0.346605 0.728853 0.204569 0.027 Uiso 1 1 calc R U . . .
C17 C 0.18211(13) 0.68269(9) 0.29019(9) 0.0215(2) Uani 1 1 d . . . . .
H17 H 0.115841 0.739634 0.269362 0.026 Uiso 1 1 calc R U . . .
C18 C 0.14664(13) 0.60625(9) 0.35837(9) 0.0185(2) Uani 1 1 d . . . . .
H18 H 0.055498 0.610599 0.386434 0.022 Uiso 1 1 calc R U . . .
B1 B 0.21770(14) 0.42689(10) 0.45735(10) 0.0152(2) 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 1.3754(14) . ?
F2 B1 1.3699(13) . ?
N1 C1 1.3123(14) . ?
N1 N2 1.3808(12) . ?
N1 B1 1.6083(15) . ?
N2 C14 1.3428(14) . ?
N3 C18 1.3594(14) . ?
N3 C14 1.3612(14) . ?
N3 B1 1.5461(15) . ?
C1 C13 1.4731(15) . ?
C1 C2 1.4787(15) . ?
C2 C3 1.3931(16) . ?
C2 C7 1.4104(16) . ?
C3 C4 1.3960(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3861(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3845(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.4651(17) . ?
C8 C9 1.3825(17) . ?
C8 C13 1.4123(16) . ?
C9 C10 1.392(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3877(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3971(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3919(16) . ?
C12 H12 0.9500 . ?
C14 C15 1.4142(15) . ?
C15 C16 1.3676(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.4136(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.3628(17) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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 N2 118.99(9) . . ?
C1 N1 B1 129.05(9) . . ?
N2 N1 B1 111.95(8) . . ?
C14 N2 N1 106.54(9) . . ?
C18 N3 C14 122.03(10) . . ?
C18 N3 B1 128.61(9) . . ?
C14 N3 B1 109.27(9) . . ?
N1 C1 C13 126.20(10) . . ?
N1 C1 C2 126.51(10) . . ?
C13 C1 C2 107.27(9) . . ?
C3 C2 C7 119.62(10) . . ?
C3 C2 C1 133.04(11) . . ?
C7 C2 C1 107.34(10) . . ?
C2 C3 C4 118.53(11) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 121.39(12) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 120.41(11) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 118.85(12) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C2 121.15(11) . . ?
C6 C7 C8 129.82(11) . . ?
C2 C7 C8 109.03(10) . . ?
C9 C8 C13 120.95(11) . . ?
C9 C8 C7 130.38(11) . . ?
C13 C8 C7 108.67(10) . . ?
C8 C9 C10 118.45(12) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 120.96(11) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 121.13(12) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 118.17(11) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C12 C13 C8 120.32(10) . . ?
C12 C13 C1 132.01(10) . . ?
C8 C13 C1 107.65(10) . . ?
N2 C14 N3 116.35(10) . . ?
N2 C14 C15 124.61(10) . . ?
N3 C14 C15 119.04(10) . . ?
C16 C15 C14 118.70(11) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 121.01(11) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 118.57(11) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
N3 C18 C17 120.61(11) . . ?
N3 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
F2 B1 F1 111.59(9) . . ?
F2 B1 N3 113.48(9) . . ?
F1 B1 N3 111.44(9) . . ?
F2 B1 N1 112.09(9) . . ?
F1 B1 N1 111.47(9) . . ?
N3 B1 N1 95.88(8) . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.047



