# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Compound1
_database_code_depnum_ccdc_archive 'CCDC 2109136'
loop_
_audit_author_name
_audit_author_address
'Guenther Redhammer'
;Paris Lodron Universitaet Salzburg
Austria
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2021-11-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H24 B F2 N5 O'
_chemical_formula_sum            'C18 H24 B F2 N5 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         375.23

_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7126(10)
_cell_length_b                   10.0034(12)
_cell_length_c                   11.8736(14)
_cell_angle_alpha                69.381(2)
_cell_angle_beta                 80.082(2)
_cell_angle_gamma                76.862(2)
_cell_volume                     938.37(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4017
_cell_measurement_theta_min      1.84
_cell_measurement_theta_max      26.89
_cell_measurement_temperature    295(2)

_exptl_crystal_description       cuboid
_exptl_crystal_colour            'red green'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396

_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        multiscan correction with APEX2 software (Bruker 2012)
;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      295(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_type            CCD
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'SMART APEX'
_diffrn_measurement_method       
'rotation, ω-scans at 4 different φ positions'

_diffrn_reflns_number            11484
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         26.89
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_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       -15
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             4017
_reflns_number_gt                2534
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1899
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_number_reflns         4017
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0940P)²+0.2687P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.303
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.36526(16) 0.37252(16) 0.82691(13) 0.0568(4) Uani d . . . 1 . .
F F2 0.36097(17) 0.56323(17) 0.65436(14) 0.0619(4) Uani d . . . 1 . .
N N1 0.1257(2) 0.5537(2) 0.79512(18) 0.0438(5) Uani d . . . 1 . .
N N2 0.2036(2) 0.3837(2) 0.67730(17) 0.0430(5) Uani d . . . 1 . .
C C11 0.0438(2) 0.3885(3) 0.6712(2) 0.0430(5) Uani d . . . 1 . .
C C7 -0.0344(3) 0.5581(2) 0.7856(2) 0.0445(6) Uani d . . . 1 . .
C C12 -0.0738(3) 0.4784(3) 0.7235(2) 0.0433(5) Uani d . . . 1 . .
C C15 0.2907(3) 0.2931(3) 0.6185(2) 0.0471(6) Uani d . . . 1 . .
O O1 -0.3019(2) 0.3766(3) 0.8120(2) 0.0773(7) Uani d . . . 1 . .
H H14 -0.394888 0.377293 0.807244 0.116 Uiso calc U . R 1 . .
C C4 0.1311(3) 0.6401(3) 0.8590(2) 0.0475(6) Uani d . . . 1 . .
C C8 -0.1280(3) 0.6540(3) 0.8483(2) 0.0478(6) Uani d . . . 1 . .
C C3 -0.0244(3) 0.7032(3) 0.8937(2) 0.0493(6) Uani d . . . 1 . .
C C17 0.0348(3) 0.2959(3) 0.6061(2) 0.0462(6) Uani d . . . 1 . .
B B1 0.2680(3) 0.4684(3) 0.7377(3) 0.0446(6) Uani d . . . 1 . .
C C16 0.1910(3) 0.2369(3) 0.5734(2) 0.0504(6) Uani d . . . 1 . .
C C21 0.4674(3) 0.2595(3) 0.6099(3) 0.0592(7) Uani d . . . 1 . .
H H21A 0.508051 0.267397 0.526912 0.071 Uiso calc U . R 1 . .
H H21B 0.504833 0.331519 0.630285 0.071 Uiso calc U . R 1 . .
C C9 -0.3048(3) 0.6971(3) 0.8657(3) 0.0619(7) Uani d . . . 1 . .
H H9A -0.332934 0.740574 0.928408 0.093 Uiso calc U . R 1 . .
H H9B -0.352591 0.612581 0.888083 0.093 Uiso calc U . R 1 . .
H H9C -0.342058 0.76563 0.79157 0.093 Uiso calc U . R 1 . .
C C13 -0.2462(3) 0.4858(3) 0.7124(3) 0.0539(7) Uani d . . . 1 . .
H H13A -0.307084 0.580211 0.711562 0.065 Uiso calc U . R 1 . .
H H13B -0.256634 0.470972 0.637778 0.065 Uiso calc U . R 1 . .
C C2 -0.0646(4) 0.8078(3) 0.9637(3) 0.0616(7) Uani d . . . 1 . .
H H2A 0.020737 0.791749 1.012308 0.074 Uiso calc U . R 1 . .
H H2B -0.159834 0.789339 1.01809 0.074 Uiso calc U . R 1 . .
C C18 -0.1073(3) 0.2606(3) 0.5762(3) 0.0648(8) Uani d . . . 1 . .
H H18A -0.075163 0.18131 0.544558 0.097 Uiso calc U . R 1 . .
H H18B -0.159005 0.344084 0.516718 0.097 Uiso calc U . R 1 . .
H H18C -0.179144 0.233832 0.647914 0.097 Uiso calc U . R 1 . .
C C5 0.2824(3) 0.6634(3) 0.8845(3) 0.0633(7) Uani d . . . 1 . .
H H5A 0.369641 0.603456 0.853801 0.095 Uiso calc U . R 1 . .
H H5B 0.283493 0.638115 0.970263 0.095 Uiso calc U . R 1 . .
H H5C 0.291667 0.76356 0.845981 0.095 Uiso calc U . R 1 . .
C C19 0.2445(3) 0.1291(3) 0.5039(3) 0.0641(8) Uani d . . . 1 . .
H H19A 0.174958 0.153411 0.441178 0.077 Uiso calc U . R 1 . .
H H19B 0.350724 0.137974 0.464777 0.077 Uiso calc U . R 1 . .
N N3 0.5317(3) 0.1142(4) 0.6894(3) 0.0920(10) Uani d . . . 1 . .
N N4 0.4594(4) 0.0724(4) 0.7875(3) 0.0916(9) Uani d . . . 1 . .
C C1 -0.0907(4) 0.9647(3) 0.8818(3) 0.0819(10) Uani d . . . 1 . .
H H1A 0.008237 0.988448 0.837982 0.123 Uiso calc U . R 1 . .
H H1B -0.132308 1.027036 0.929756 0.123 Uiso calc U . R 1 . .
H H1C -0.164549 0.97788 0.825695 0.123 Uiso calc U . R 1 . .
C C20 0.2436(5) -0.0223(4) 0.5820(4) 0.0946(12) Uani d . . . 1 . .
H H20A 0.318618 -0.049572 0.640245 0.142 Uiso calc U . R 1 . .
H H20B 0.272031 -0.084928 0.533409 0.142 Uiso calc U . R 1 . .
H H20C 0.13963 -0.031084 0.623272 0.142 Uiso calc U . R 1 . .
N N5 0.3964(6) 0.0176(5) 0.8784(4) 0.158(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 B1 . 1.409(3) ?
F2 B1 . 1.395(3) ?
N1 C4 . 1.348(3) ?
N1 C7 . 1.408(3) ?
N1 B1 . 1.540(3) ?
N2 C15 . 1.355(3) ?
N2 C11 . 1.395(3) ?
N2 B1 . 1.526(3) ?
C11 C12 . 1.414(3) ?
C11 C17 . 1.421(3) ?
C7 C12 . 1.386(3) ?
C7 C8 . 1.441(3) ?
C12 C13 . 1.514(3) ?
C15 C16 . 1.397(4) ?
C15 C21 . 1.492(3) ?
O1 C13 . 1.401(3) ?
O1 H14 . 0.82 ?
C4 C3 . 1.416(3) ?
C4 C5 . 1.487(3) ?
C8 C3 . 1.380(4) ?
C8 C9 . 1.501(3) ?
C3 C2 . 1.501(4) ?
C17 C16 . 1.402(3) ?
C17 C18 . 1.491(3) ?
C16 C19 . 1.526(4) ?
C21 N3 . 1.471(4) ?
C21 H21A . 0.97 ?
C21 H21B . 0.97 ?
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 0.96 ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C2 C1 . 1.516(4) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C5 H5A . 0.96 ?
C5 H5B . 0.96 ?
C5 H5C . 0.96 ?
C19 C20 . 1.472(5) ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
N3 N4 . 1.205(4) ?
N4 N5 . 1.132(5) ?
C1 H1A . 0.96 ?
C1 H1B . 0.96 ?
C1 H1C . 0.96 ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 N1 C7 . . 108.22(19) ?
C4 N1 B1 . . 126.72(19) ?
C7 N1 B1 . . 125.02(19) ?
C15 N2 C11 . . 108.05(19) ?
C15 N2 B1 . . 126.23(19) ?
C11 N2 B1 . . 125.71(19) ?
N2 C11 C12 . . 119.8(2) ?
N2 C11 C17 . . 107.91(19) ?
C12 C11 C17 . . 132.3(2) ?
C12 C7 N1 . . 120.1(2) ?
C12 C7 C8 . . 132.9(2) ?
N1 C7 C8 . . 107.0(2) ?
C7 C12 C11 . . 121.4(2) ?
C7 C12 C13 . . 119.6(2) ?
C11 C12 C13 . . 119.0(2) ?
N2 C15 C16 . . 110.0(2) ?
N2 C15 C21 . . 122.5(2) ?
C16 C15 C21 . . 127.4(2) ?
C13 O1 H14 . . 109.5 ?
N1 C4 C3 . . 110.1(2) ?
N1 C4 C5 . . 122.8(2) ?
C3 C4 C5 . . 127.2(2) ?
C3 C8 C7 . . 107.4(2) ?
C3 C8 C9 . . 123.6(2) ?
C7 C8 C9 . . 129.1(2) ?
C8 C3 C4 . . 107.4(2) ?
C8 C3 C2 . . 127.5(2) ?
C4 C3 C2 . . 125.1(2) ?
C16 C17 C11 . . 106.8(2) ?
C16 C17 C18 . . 123.7(2) ?
C11 C17 C18 . . 129.5(2) ?
F2 B1 F1 . . 106.99(19) ?
F2 B1 N2 . . 111.4(2) ?
F1 B1 N2 . . 110.3(2) ?
F2 B1 N1 . . 110.2(2) ?
F1 B1 N1 . . 110.2(2) ?
N2 B1 N1 . . 107.78(18) ?
C15 C16 C17 . . 107.2(2) ?
C15 C16 C19 . . 125.7(2) ?
C17 C16 C19 . . 127.1(2) ?
N3 C21 C15 . . 113.8(2) ?
N3 C21 H21A . . 108.8 ?
C15 C21 H21A . . 108.8 ?
N3 C21 H21B . . 108.8 ?
C15 C21 H21B . . 108.8 ?
H21A C21 H21B . . 107.7 ?
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 ?
O1 C13 C12 . . 107.7(2) ?
O1 C13 H13A . . 110.2 ?
C12 C13 H13A . . 110.2 ?
O1 C13 H13B . . 110.2 ?
C12 C13 H13B . . 110.2 ?
H13A C13 H13B . . 108.5 ?
C3 C2 C1 . . 112.3(2) ?
C3 C2 H2A . . 109.2 ?
C1 C2 H2A . . 109.2 ?
C3 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C20 C19 C16 . . 112.8(2) ?
C20 C19 H19A . . 109.0 ?
C16 C19 H19A . . 109.0 ?
C20 C19 H19B . . 109.0 ?
C16 C19 H19B . . 109.0 ?
H19A C19 H19B . . 107.8 ?
N4 N3 C21 . . 116.2(3) ?
N5 N4 N3 . . 172.1(4) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?




_publcif_funding_html            
;
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-heptane/ethyl acetate'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_Compound4
_database_code_depnum_ccdc_archive 'CCDC 2109137'
loop_
_audit_author_name
_audit_author_address
'Guenther Redhammer'
;Paris Lodron Universitaet Salzburg
Austria
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2021-11-16 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H27 B F2 N2 O2'
_chemical_formula_sum            'C20 H27 B F2 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         376.24

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   17.1373(13)
_cell_length_b                   11.7136(9)
_cell_length_c                   20.6062(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.0460(10)
_cell_angle_gamma                90
_cell_volume                     4085.0(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3499
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      24.77
_cell_measurement_temperature    295(2)

_exptl_crystal_description       cuboid
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600

_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        multiscan correction with APEX2 software (Bruker 2012)
;
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99


_exptl_special_details           
;
;

_diffrn_ambient_temperature      295(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector_type            CCD
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'SMART APEX'
_diffrn_measurement_method       
'rotation, ω-scans at 4 different φ positions'

_diffrn_reflns_number            21021
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         24.77
_diffrn_reflns_theta_full        24.77
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
;

_reflns_number_total             3499
_reflns_number_gt                2485
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_gt          0.1935
_refine_ls_wR_factor_ref         0.2163
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_number_reflns         3499
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0992P)²+3.2606P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'
O O 0.0106 0.0060 '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'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.37873(13) 0.40523(18) 0.12979(9) 0.1167(7) Uani d . . . 1 . .
F F2 0.25763(11) 0.43453(18) 0.15645(11) 0.1168(7) Uani d . . . 1 . .
B B1 0.3378(2) 0.4544(3) 0.17564(18) 0.0799(9) Uani d . . . 1 . .
N N1 0.35338(14) 0.5831(2) 0.18044(11) 0.0760(7) Uani d . . . 1 . .
C C1 0.38261(16) 0.6422(3) 0.23762(13) 0.0731(7) Uani d . . . 1 . .
C C2 0.40887(15) 0.5823(2) 0.29553(13) 0.0692(7) Uani d . . . 1 . .
C C3 0.39983(15) 0.4644(2) 0.29936(13) 0.0703(7) Uani d . . . 1 . .
N N2 0.36480(13) 0.4034(2) 0.24413(11) 0.0748(6) Uani d . . . 1 . .
C C4 0.3245(2) 0.2026(3) 0.2149(2) 0.1188(13) Uani d . . . 1 . .
H H4A 0.325885 0.130528 0.237225 0.178 Uiso calc U . R 1 . .
H H4B 0.354261 0.197297 0.179258 0.178 Uiso calc U . R 1 . .
H H4C 0.270701 0.222076 0.197987 0.178 Uiso calc U . R 1 . .
C C5 0.35956(18) 0.2926(3) 0.26187(18) 0.0872(9) Uani d . . . 1 . .
C C6 0.39101(19) 0.2788(3) 0.32885(18) 0.0904(9) Uani d . . . 1 . .
C C7 0.41656(17) 0.3855(3) 0.35312(15) 0.0814(8) Uani d . . . 1 . .
C C8 0.4506(2) 0.4088(3) 0.42316(16) 0.1025(11) Uani d . . . 1 . .
H H8A 0.421198 0.468927 0.439845 0.154 Uiso calc U . R 1 . .
H H8B 0.504801 0.431577 0.425832 0.154 Uiso calc U . R 1 . .
H H8C 0.447567 0.340996 0.448794 0.154 Uiso calc U . R 1 . .
C C9 0.3959(2) 0.1675(3) 0.3667(2) 0.1186(13) Uani d . . . 1 . .
H H9A 0.388605 0.182349 0.411668 0.142 Uiso calc U . R 1 . .
H H9B 0.353712 0.117114 0.347064 0.142 Uiso calc U . R 1 . .
C C10 0.4743(3) 0.1096(4) 0.3665(2) 0.1422(17) Uani d . . . 1 . .
H H10A 0.477518 0.042858 0.393834 0.213 Uiso calc U . R 1 . .
H H10B 0.516218 0.16125 0.38314 0.213 Uiso calc U . R 1 . .
H H10C 0.47925 0.087817 0.322418 0.213 Uiso calc U . R 1 . .
C C11 0.45027(16) 0.6457(3) 0.35432(14) 0.0791(8) Uani d . . . 1 . .
H H11A 0.488575 0.596381 0.380332 0.095 Uiso calc U . R 1 . .
H H11B 0.477844 0.71139 0.340409 0.095 Uiso calc U . R 1 . .
O O1 0.39128(12) 0.68185(19) 0.39261(10) 0.0868(6) Uani d . . . 1 . .
C C12 0.4162(2) 0.7565(3) 0.44106(15) 0.0937(10) Uani d . . . 1 . .
O O2 0.4831(2) 0.7889(3) 0.45186(13) 0.1275(10) Uani d . . . 1 . .
C C13 0.3506(3) 0.7860(5) 0.4776(2) 0.1442(18) Uani d . . . 1 . .
H H13A 0.300839 0.771284 0.45029 0.216 Uiso calc U . R 1 . .
H H13B 0.353843 0.865343 0.489375 0.216 Uiso calc U . R 1 . .
H H13C 0.354672 0.740367 0.516693 0.216 Uiso calc U . R 1 . .
C C14 0.3056(3) 0.6252(4) 0.06234(17) 0.1244(14) Uani d . . . 1 . .
H H14A 0.339427 0.567371 0.049033 0.187 Uiso calc U . R 1 . .
H H14B 0.304722 0.689989 0.033681 0.187 Uiso calc U . R 1 . .
H H14C 0.253002 0.595417 0.059984 0.187 Uiso calc U . R 1 . .
C C15 0.3359(2) 0.6609(3) 0.13121(16) 0.0942(10) Uani d . . . 1 . .
C C16 0.3534(3) 0.7704(3) 0.15627(19) 0.1094(12) Uani d . . . 1 . .
C C17 0.3808(2) 0.7608(3) 0.22264(17) 0.0924(9) Uani d . . . 1 . .
C C18 0.3997(3) 0.8608(3) 0.2686(2) 0.1235(14) Uani d . . . 1 . .
H H18A 0.39288 0.930628 0.243973 0.185 Uiso calc U . R 1 . .
H H18B 0.453438 0.85509 0.290234 0.185 Uiso calc U . R 1 . .
H H18C 0.364893 0.860254 0.300804 0.185 Uiso calc U . R 1 . .
C C19 0.3511(3) 0.8861(5) 0.1132(3) 0.1422(17) Uani d . . . 1 . .
H H19A 0.3909 0.939967 0.132843 0.171 Uiso calc U . R 1 . .
H H19B 0.359236 0.869844 0.068586 0.171 Uiso calc U . R 1 . .
C C20 0.2751(3) 0.9283(5) 0.1143(2) 0.157(2) Uani d . . . 1 . .
H H20A 0.267057 0.995863 0.087812 0.235 Uiso calc U . R 1 . .
H H20B 0.269214 0.946348 0.158751 0.235 Uiso calc U . R 1 . .
H H20C 0.236927 0.87153 0.097294 0.235 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 B1 . 1.387(4) ?
F2 B1 . 1.388(4) ?
B1 N1 . 1.532(4) ?
B1 N2 . 1.535(4) ?
N1 C15 . 1.362(4) ?
N1 C1 . 1.390(3) ?
C1 C2 . 1.396(4) ?
C1 C17 . 1.423(4) ?
C2 C3 . 1.393(4) ?
C2 C11 . 1.501(4) ?
C3 N2 . 1.397(3) ?
C3 C7 . 1.437(4) ?
N2 C5 . 1.355(4) ?
C4 C5 . 1.493(5) ?
C5 C6 . 1.410(5) ?
C6 C7 . 1.390(4) ?
C6 C9 . 1.516(5) ?
C7 C8 . 1.494(4) ?
C9 C10 . 1.507(6) ?
C11 O1 . 1.440(3) ?
O1 C12 . 1.345(4) ?
C12 O2 . 1.194(4) ?
C12 C13 . 1.490(5) ?
C14 C15 . 1.492(5) ?
C15 C16 . 1.398(5) ?
C16 C17 . 1.379(5) ?
C16 C19 . 1.618(6) ?
C17 C18 . 1.509(5) ?
C19 C20 . 1.395(6) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 B1 F2 . . 108.7(3) ?
F1 B1 N1 . . 110.5(3) ?
F2 B1 N1 . . 109.7(3) ?
F1 B1 N2 . . 110.7(3) ?
F2 B1 N2 . . 109.8(3) ?
N1 B1 N2 . . 107.4(2) ?
C15 N1 C1 . . 107.8(3) ?
C15 N1 B1 . . 126.5(3) ?
C1 N1 B1 . . 125.5(2) ?
N1 C1 C2 . . 119.9(3) ?
N1 C1 C17 . . 108.0(3) ?
C2 C1 C17 . . 132.0(3) ?
C3 C2 C1 . . 121.5(3) ?
C3 C2 C11 . . 119.2(3) ?
C1 C2 C11 . . 119.3(3) ?
C2 C3 N2 . . 119.9(3) ?
C2 C3 C7 . . 132.1(3) ?
N2 C3 C7 . . 107.9(3) ?
C5 N2 C3 . . 107.9(2) ?
C5 N2 B1 . . 126.7(3) ?
C3 N2 B1 . . 125.4(2) ?
N2 C5 C6 . . 110.0(3) ?
N2 C5 C4 . . 122.6(3) ?
C6 C5 C4 . . 127.4(3) ?
C7 C6 C5 . . 107.4(3) ?
C7 C6 C9 . . 126.8(3) ?
C5 C6 C9 . . 125.7(3) ?
C6 C7 C3 . . 106.7(3) ?
C6 C7 C8 . . 124.4(3) ?
C3 C7 C8 . . 128.8(3) ?
C10 C9 C6 . . 111.3(4) ?
O1 C11 C2 . . 107.7(2) ?
C12 O1 C11 . . 115.4(3) ?
O2 C12 O1 . . 121.9(3) ?
O2 C12 C13 . . 127.7(4) ?
O1 C12 C13 . . 110.4(4) ?
N1 C15 C16 . . 109.2(3) ?
N1 C15 C14 . . 121.6(3) ?
C16 C15 C14 . . 129.1(3) ?
C17 C16 C15 . . 108.2(3) ?
C17 C16 C19 . . 126.0(4) ?
C15 C16 C19 . . 125.5(4) ?
C16 C17 C1 . . 106.7(3) ?
C16 C17 C18 . . 124.4(3) ?
C1 C17 C18 . . 128.8(3) ?
C20 C19 C16 . . 103.3(4) ?




_publcif_funding_html            
;
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-heptane/ethyl acetate'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
_exptl_crystal_preparation       Luminescent
