# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2243651'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          304
_chemical_formula_moiety         'C19 H10 B F2 N3 O'
_chemical_formula_sum            'C19 H10 B F2 N3 O'
_chemical_formula_weight         345.11

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'
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'
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'

_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                   11.5664(16)
_cell_length_b                   19.025(2)
_cell_length_c                   7.3449(9)
_cell_angle_alpha                90
_cell_angle_beta                 108.050(14)
_cell_angle_gamma                90
_cell_volume                     1536.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1926
_cell_measurement_theta_min      2.7750
_cell_measurement_theta_max      29.6960

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.111
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.102
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -5 3 0.0084
0 -5 0 0.1006
-1 5 1 0.0558
0 0 0 0.0527
0 0 0 0.0496
0 -5 4 0.0100
-1 -5 0 0.1023
-1 -5 4 0.0082
3 -3 -1 0.0754
2 5 -5 0.1755
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0188 -5.0332 2.9993 0.0003 0.0548 -0.3415
0.4923 -5.0158 -0.0020 0.0441 0.1671 -0.0779
-0.9959 5.0101 1.0025 -0.0587 -0.2046 -0.0099
0.4988 -0.0001 0.0012 0.0318 -0.0039 -0.0034
-0.4988 0.0001 -0.0012 -0.0318 0.0039 0.0034
-0.0260 -5.0394 4.0035 0.0811 0.0057 -0.4396
-1.0041 -5.0155 -0.0058 -0.0514 0.1787 -0.0677
-1.0237 -5.0391 4.0010 0.0175 0.0134 -0.4328
2.9938 -3.0043 -0.9962 0.1810 0.1208 0.0261
1.5273 5.0449 -5.0014 -0.0029 0.0240 0.5206
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.326
_oxdiff_exptl_absorpt_empirical_full_max 4.953
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2195
_diffrn_reflns_number            8467
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.139
_diffrn_reflns_theta_max         30.509
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.793
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.793
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_point_group_measured_fraction_full 0.957
_reflns_number_total             3730
_reflns_number_gt                2252
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+0.4266P] 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         3730
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1488
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
F2 F 1.16715(12) 0.44833(8) 0.8011(2) 0.0293(4) Uani 1 1 d . . . . .
F1 F 1.17692(12) 0.32110(8) 0.6745(2) 0.0306(4) Uani 1 1 d . . . . .
O1 O 0.65944(15) 0.35658(9) 0.6158(2) 0.0239(4) Uani 1 1 d . . . . .
N3 N 0.65675(18) 0.39046(10) 0.3008(3) 0.0198(5) Uani 1 1 d . . . . .
N2 N 1.02948(19) 0.53223(11) 0.7886(3) 0.0233(5) Uani 1 1 d . . . . .
N1 N 1.04906(19) 0.23058(11) 0.5711(3) 0.0247(5) Uani 1 1 d . . . . .
C15 C 0.5444(2) 0.36937(13) 0.3036(3) 0.0206(5) Uani 1 1 d . . . . .
C6 C 0.9592(2) 0.41908(13) 0.6510(3) 0.0193(5) Uani 1 1 d . . . . .
C1 C 0.9648(2) 0.34453(13) 0.5942(3) 0.0194(5) Uani 1 1 d . . . . .
C8 C 0.8154(2) 0.51057(14) 0.6520(3) 0.0239(6) Uani 1 1 d . . . . .
H8 H 0.7344 0.5275 0.6223 0.029 Uiso 1 1 calc R U . . .
C19 C 0.3339(2) 0.34082(14) 0.1732(4) 0.0247(6) Uani 1 1 d . . . . .
H19 H 0.2600 0.3384 0.0703 0.030 Uiso 1 1 calc R U . . .
C16 C 0.5477(2) 0.34725(13) 0.4873(3) 0.0207(5) Uani 1 1 d . . . . .
C14 C 0.4405(2) 0.36819(13) 0.1427(3) 0.0219(6) Uani 1 1 d . . . . .
C11 C 0.6716(2) 0.41183(14) 0.1372(3) 0.0234(6) Uani 1 1 d . . . . .
H11 H 0.7498 0.4256 0.1333 0.028 Uiso 1 1 calc R U . . .
C10 C 1.0482(2) 0.46738(13) 0.7445(3) 0.0211(5) Uani 1 1 d . . . . .
C13 C 0.4579(2) 0.39283(14) -0.0288(3) 0.0234(6) Uani 1 1 d . . . . .
H13 H 0.3912 0.3948 -0.1433 0.028 Uiso 1 1 calc R U . . .
C7 C 0.8376(2) 0.44202(13) 0.6062(3) 0.0198(5) Uani 1 1 d . . . . .
C3 C 0.8330(2) 0.24627(13) 0.4704(3) 0.0231(6) Uani 1 1 d . . . . .
H3 H 0.7542 0.2267 0.4167 0.028 Uiso 1 1 calc R U . . .
C2 C 0.8468(2) 0.31688(13) 0.5159(3) 0.0204(5) Uani 1 1 d . . . . .
C18 C 0.3381(2) 0.31776(14) 0.3527(4) 0.0252(6) Uani 1 1 d . . . . .
H18 H 0.2659 0.2991 0.3697 0.030 Uiso 1 1 calc R U . . .
C4 C 0.9351(2) 0.20464(14) 0.5041(3) 0.0239(6) Uani 1 1 d . . . . .
H4 H 0.9247 0.1557 0.4792 0.029 Uiso 1 1 calc R U . . .
C5 C 1.0599(2) 0.29806(14) 0.6109(3) 0.0216(5) Uani 1 1 d . . . . .
C17 C 0.4442(2) 0.32030(14) 0.5136(3) 0.0234(6) Uani 1 1 d . . . . .
H17 H 0.4436 0.3039 0.6354 0.028 Uiso 1 1 calc R U . . .
C12 C 0.5715(2) 0.41389(14) -0.0297(3) 0.0252(6) Uani 1 1 d . . . . .
H12 H 0.5822 0.4301 -0.1457 0.030 Uiso 1 1 calc R U . . .
C9 C 0.9129(2) 0.55404(14) 0.7417(3) 0.0241(6) Uani 1 1 d . . . . .
H9 H 0.8969 0.6009 0.7713 0.029 Uiso 1 1 calc R U . . .
B1 B 0.7484(3) 0.37740(16) 0.5128(4) 0.0224(6) 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
F2 C10 1.357(3) . ?
F1 C5 1.360(3) . ?
O1 C16 1.355(3) . ?
O1 B1 1.507(3) . ?
N3 C11 1.330(3) . ?
N3 C15 1.366(3) . ?
N3 B1 1.609(3) . ?
N2 C10 1.311(3) . ?
N2 C9 1.350(3) . ?
N1 C5 1.314(3) . ?
N1 C4 1.350(3) . ?
C15 C14 1.401(3) . ?
C15 C16 1.403(3) . ?
C6 C10 1.392(3) . ?
C6 C7 1.411(3) . ?
C6 C1 1.485(3) . ?
C1 C5 1.387(3) . ?
C1 C2 1.409(3) . ?
C8 C9 1.389(3) . ?
C8 C7 1.391(3) . ?
C8 H8 0.9500 . ?
C19 C18 1.376(4) . ?
C19 C14 1.419(3) . ?
C19 H19 0.9500 . ?
C16 C17 1.369(3) . ?
C14 C13 1.416(4) . ?
C11 C12 1.402(3) . ?
C11 H11 0.9500 . ?
C13 C12 1.375(3) . ?
C13 H13 0.9500 . ?
C7 B1 1.615(4) . ?
C3 C4 1.379(3) . ?
C3 C2 1.382(3) . ?
C3 H3 0.9500 . ?
C2 B1 1.614(4) . ?
C18 C17 1.417(3) . ?
C18 H18 0.9500 . ?
C4 H4 0.9500 . ?
C17 H17 0.9500 . ?
C12 H12 0.9500 . ?
C9 H9 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
C16 O1 B1 109.74(18) . . ?
C11 N3 C15 119.6(2) . . ?
C11 N3 B1 133.7(2) . . ?
C15 N3 B1 106.55(19) . . ?
C10 N2 C9 117.1(2) . . ?
C5 N1 C4 117.0(2) . . ?
N3 C15 C14 124.3(2) . . ?
N3 C15 C16 111.1(2) . . ?
C14 C15 C16 124.6(2) . . ?
C10 C6 C7 116.3(2) . . ?
C10 C6 C1 132.8(2) . . ?
C7 C6 C1 110.9(2) . . ?
C5 C1 C2 116.1(2) . . ?
C5 C1 C6 133.3(2) . . ?
C2 C1 C6 110.5(2) . . ?
C9 C8 C7 119.3(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C18 C19 C14 119.6(2) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
O1 C16 C17 129.6(2) . . ?
O1 C16 C15 111.5(2) . . ?
C17 C16 C15 118.9(2) . . ?
C15 C14 C13 115.1(2) . . ?
C15 C14 C19 115.7(2) . . ?
C13 C14 C19 129.2(2) . . ?
N3 C11 C12 119.7(2) . . ?
N3 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
N2 C10 F2 113.9(2) . . ?
N2 C10 C6 126.1(2) . . ?
F2 C10 C6 119.9(2) . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C8 C7 C6 118.6(2) . . ?
C8 C7 B1 132.5(2) . . ?
C6 C7 B1 108.8(2) . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 B1 131.4(2) . . ?
C1 C2 B1 109.2(2) . . ?
C19 C18 C17 123.5(2) . . ?
C19 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
N1 C4 C3 122.7(2) . . ?
N1 C4 H4 118.6 . . ?
C3 C4 H4 118.6 . . ?
N1 C5 F1 114.1(2) . . ?
N1 C5 C1 125.8(2) . . ?
F1 C5 C1 120.2(2) . . ?
C16 C17 C18 117.7(2) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
N2 C9 C8 122.6(2) . . ?
N2 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
O1 B1 N3 100.27(18) . . ?
O1 B1 C2 113.2(2) . . ?
N3 B1 C2 112.0(2) . . ?
O1 B1 C7 115.6(2) . . ?
N3 B1 C7 115.9(2) . . ?
C2 B1 C7 100.5(2) . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-4

_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_7
_database_code_depnum_ccdc_archive 'CCDC 2293837'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology
Poland
;
_audit_update_record             
;
2023-09-08 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 2,4,5,7-Tetrafluoro-3,6-diaza-9-hydroxy-9-borafluorene 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H5 B F4 N2 O2'
_chemical_formula_sum            'C10 H5 B F4 N2 O2'
_chemical_formula_weight         271.97

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'
O O 0.0492 0.0322 '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      tetragonal
_space_group_IT_number           122
_space_group_name_H-M_alt        'I -4 2 d'
_space_group_name_Hall           'I -4 2bw'

_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'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y, -z+3/4'
'x+1/2, -y, -z+3/4'
'-y+1/2, -x, z+3/4'
'y+1/2, x, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'-x+1, y+1/2, -z+5/4'
'x+1, -y+1/2, -z+5/4'
'-y+1, -x+1/2, z+5/4'
'y+1, x+1/2, z+5/4'

_cell_length_a                   22.1078(2)
_cell_length_b                   22.1078(2)
_cell_length_c                   4.35580(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2128.92(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4706
_cell_measurement_theta_min      3.9570
_cell_measurement_theta_max      77.1730

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    1.462
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.039
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
11 -9 0 0.0153
-10 10 0 0.0214
-10 -10 0 0.0249
11 9 0 0.0355
1 3 3 0.0772
-2 -3 -3 0.0656
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
11.0104 -9.0019 0.0016 -0.1046 0.1778 0.9689
-10.0089 10.0004 -0.0012 0.0335 -0.1102 -0.9788
-10.0147 -9.9845 -0.0042 0.7109 -0.6760 0.0990
11.0156 8.9845 0.0043 -0.7142 0.6870 -0.0011
0.9956 2.9895 3.0012 -0.8735 -0.6389 -0.0559
-1.9968 -2.9887 -3.0015 0.9107 0.5996 0.0119
_exptl_absorpt_correction_T_min  0.877
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.798
_oxdiff_exptl_absorpt_empirical_full_max 1.500
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000

_diffrn_reflns_number            7990
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.999
_diffrn_reflns_theta_max         77.357
_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             1146
_reflns_number_gt                1123
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'

_refine_special_details          'Refined as a 2-component inversion twin.,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)+(0.0381P)²+1.1538P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.52(19)
_refine_ls_number_reflns         1146
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0685
_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 0.06573(5) 0.06004(5) 0.1183(3) 0.0324(3) Uani 1 1 d . . . . .
F2 F 0.19316(6) 0.19721(7) 0.4990(5) 0.0558(5) Uani 1 1 d . . . . .
O1 O -0.05773(5) 0.22705(5) 0.8754(3) 0.0174(3) Uani 1 1 d . . . . .
C3 C 0.02937(8) 0.20023(8) 0.4928(4) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.02042(8) 0.14506(8) 0.3479(4) 0.0198(4) Uani 1 1 d . . . . .
H2 H -0.0190 0.1298 0.3095 0.024 Uiso 1 1 calc R U . . .
C1 C 0.07145(8) 0.11337(8) 0.2620(4) 0.0229(4) Uani 1 1 d . . . . .
N1 N 0.12792(7) 0.13042(8) 0.3087(5) 0.0279(4) Uani 1 1 d . . . . .
B1 B -0.01852(11) 0.2500 0.6250 0.0149(5) Uani 1 2 d S T P . .
C4 C 0.13551(8) 0.18288(9) 0.4508(6) 0.0304(5) Uani 1 1 d . . . . .
C5 C 0.08892(8) 0.22022(8) 0.5467(4) 0.0216(4) Uani 1 1 d . . . . .
H1A H -0.0797(13) 0.1969(13) 0.830(7) 0.037(7) Uiso 1 1 d . . . . .
H1B H -0.064(2) 0.2500 1.1250 0.073(16) Uiso 1 2 d S . P . .


_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 C1 1.341(2) . ?
F2 C4 1.330(2) . ?
O1 B1 1.4825(17) . ?
O1 H1A 0.85(3) . ?
O1 H1B 1.208(6) . ?
C3 C2 1.388(2) . ?
C3 C5 1.408(2) . ?
C3 B1 1.632(2) . ?
C2 C1 1.380(2) . ?
C2 H2 0.9500 . ?
C1 N1 1.320(2) . ?
N1 C4 1.325(3) . ?
B1 O1 1.4825(17) 14_455 ?
B1 C3 1.632(2) 14_455 ?
C4 C5 1.384(3) . ?
C5 C5 1.483(4) 14_455 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 H1A 115.6(19) . . ?
B1 O1 H1B 125.9(16) . . ?
H1A O1 H1B 118(3) . . ?
C2 C3 C5 119.01(16) . . ?
C2 C3 B1 131.34(15) . . ?
C5 C3 B1 109.64(14) . . ?
C1 C2 C3 116.93(16) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
N1 C1 F1 114.33(16) . . ?
N1 C1 C2 125.94(17) . . ?
F1 C1 C2 119.73(16) . . ?
C1 N1 C4 116.20(16) . . ?
O1 B1 O1 108.45(18) 14_455 . ?
O1 B1 C3 110.52(8) 14_455 . ?
O1 B1 C3 114.09(8) . . ?
O1 B1 C3 114.09(8) 14_455 14_455 ?
O1 B1 C3 110.52(8) . 14_455 ?
C3 B1 C3 99.09(17) . 14_455 ?
N1 C4 F2 113.80(17) . . ?
N1 C4 C5 124.65(18) . . ?
F2 C4 C5 121.55(18) . . ?
C4 C5 C3 117.26(16) . . ?
C4 C5 C5 131.93(11) . 14_455 ?
C3 C5 C5 110.81(10) . 14_455 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C3 C2 C1 -0.7(3) . . . . ?
B1 C3 C2 C1 179.80(15) . . . . ?
C3 C2 C1 N1 0.9(3) . . . . ?
C3 C2 C1 F1 -179.34(17) . . . . ?
F1 C1 N1 C4 -179.86(18) . . . . ?
C2 C1 N1 C4 -0.1(3) . . . . ?
C2 C3 B1 O1 -60.3(2) . . . 14_455 ?
C5 C3 B1 O1 120.21(16) . . . 14_455 ?
C2 C3 B1 O1 62.2(2) . . . . ?
C5 C3 B1 O1 -117.28(16) . . . . ?
C2 C3 B1 C3 179.7(2) . . . 14_455 ?
C5 C3 B1 C3 0.13(10) . . . 14_455 ?
C1 N1 C4 F2 178.40(19) . . . . ?
C1 N1 C4 C5 -0.9(3) . . . . ?
N1 C4 C5 C3 1.1(3) . . . . ?
F2 C4 C5 C3 -178.2(2) . . . . ?
N1 C4 C5 C5 -179.2(3) . . . 14_455 ?
F2 C4 C5 C5 1.5(4) . . . 14_455 ?
C2 C3 C5 C4 -0.2(3) . . . . ?
B1 C3 C5 C4 179.42(16) . . . . ?
C2 C3 C5 C5 -179.93(19) . . . 14_455 ?
B1 C3 C5 C5 -0.3(3) . . . 14_455 ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 2243653'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          298
_chemical_formula_moiety         'C23 H12 B F2 N3 O2'
_chemical_formula_sum            'C23 H12 B F2 N3 O2'
_chemical_formula_weight         411.17

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_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                   6.99430(10)
_cell_length_b                   20.8883(2)
_cell_length_c                   12.21620(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.4420(10)
_cell_angle_gamma                90
_cell_volume                     1773.51(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13000
_cell_measurement_theta_min      3.6620
_cell_measurement_theta_max      77.2540

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.956
_exptl_crystal_size_max          0.538
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.103
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -5 0 0.0607
-2 5 1 0.0621
1 -5 1 0.0882
-1 -2 5 0.2032
4 -4 -5 0.1629
-1 5 -3 0.1779
0 -1 0 0.0804
0 1 0 0.0629
2 5 0 0.0511
-2 -5 0 0.0781
-2 -1 0 0.0543
2 1 0 0.0487
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.9977 -4.9956 -0.0058 0.1449 0.5511 0.0849
-1.9979 4.9928 1.0058 -0.2008 -0.5424 0.0287
0.9975 -4.9978 0.9951 0.1709 0.3558 0.2266
-1.0020 -2.0110 4.9992 -0.0741 -0.1034 0.6526
3.9992 -3.9841 -5.0069 0.1988 0.8871 -0.5676
-0.9970 5.0034 -2.9950 -0.0591 -0.3731 -0.4538
-0.0005 -0.9989 -0.0008 0.0617 0.0286 0.0282
0.0005 0.9989 0.0008 -0.0617 -0.0286 -0.0282
2.0022 4.9931 0.0018 -0.4726 0.2648 -0.1972
-2.0022 -4.9931 -0.0018 0.4726 -0.2648 0.1972
-2.0004 -0.9976 0.0013 0.2256 -0.3793 0.0843
2.0004 0.9976 -0.0013 -0.2256 0.3793 -0.0843
_exptl_absorpt_correction_T_min  0.583
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.835
_oxdiff_exptl_absorpt_empirical_full_max 1.383
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000

_diffrn_reflns_number            18447
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.212
_diffrn_reflns_theta_max         77.495
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3734
_reflns_number_gt                3491
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'

_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)+(0.0460P)²+0.7958P] 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         3734
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
O2 O 0.23122(11) 0.51841(4) 0.55659(6) 0.01545(17) Uani 1 1 d . . . . .
F1 F 0.01864(12) 0.59018(4) -0.08827(6) 0.0324(2) Uani 1 1 d . . . . .
F2 F 0.33334(13) 0.65732(5) -0.04118(6) 0.0384(2) Uani 1 1 d . . . . .
O1 O -0.02207(12) 0.66345(4) 0.36913(6) 0.01782(18) Uani 1 1 d . . . . .
N3 N 0.16511(13) 0.56344(4) 0.39221(7) 0.01416(19) Uani 1 1 d . . . . .
N2 N -0.21922(16) 0.54884(5) -0.00297(9) 0.0257(2) Uani 1 1 d . . . . .
C23 C 0.24339(15) 0.50294(5) 0.37475(9) 0.0152(2) Uani 1 1 d . . . . .
C7 C -0.04275(17) 0.58791(5) 0.20236(9) 0.0166(2) Uani 1 1 d . . . . .
C12 C -0.06037(16) 0.72854(5) 0.52333(10) 0.0186(2) Uani 1 1 d . . . . .
H12 H -0.1236 0.7602 0.4767 0.022 Uiso 1 1 calc R U . . .
C17 C 0.16463(15) 0.57034(5) 0.49940(9) 0.0143(2) Uani 1 1 d . . . . .
C18 C 0.28322(15) 0.47530(5) 0.47793(9) 0.0150(2) Uani 1 1 d . . . . .
C21 C 0.36292(17) 0.41004(6) 0.29641(10) 0.0201(2) Uani 1 1 d . . . . .
H21 H 0.3933 0.3864 0.2342 0.024 Uiso 1 1 calc R U . . .
C16 C 0.10059(16) 0.62660(5) 0.55054(9) 0.0153(2) Uani 1 1 d . . . . .
C13 C -0.03708(17) 0.73710(6) 0.63655(10) 0.0200(2) Uani 1 1 d . . . . .
H13 H -0.0841 0.7752 0.6665 0.024 Uiso 1 1 calc R U . . .
C20 C 0.39941(16) 0.38244(5) 0.40131(10) 0.0193(2) Uani 1 1 d . . . . .
H20 H 0.4523 0.3405 0.4081 0.023 Uiso 1 1 calc R U . . .
C6 C 0.04453(17) 0.60064(6) 0.10636(9) 0.0178(2) Uani 1 1 d . . . . .
C11 C 0.00960(15) 0.67311(5) 0.47835(9) 0.0156(2) Uani 1 1 d . . . . .
C2 C 0.25752(16) 0.64969(5) 0.24753(9) 0.0175(2) Uani 1 1 d . . . . .
C15 C 0.12107(16) 0.63568(6) 0.66519(9) 0.0181(2) Uani 1 1 d . . . . .
H15 H 0.1808 0.6038 0.7128 0.022 Uiso 1 1 calc R U . . .
C8 C -0.21711(17) 0.55549(6) 0.19334(10) 0.0202(2) Uani 1 1 d . . . . .
H8 H -0.2786 0.5463 0.2570 0.024 Uiso 1 1 calc R U . . .
C22 C 0.28376(17) 0.47085(6) 0.28027(10) 0.0182(2) Uani 1 1 d . . . . .
H22 H 0.2588 0.4893 0.2090 0.022 Uiso 1 1 calc R U . . .
C19 C 0.36013(16) 0.41488(5) 0.49583(10) 0.0176(2) Uani 1 1 d . . . . .
H19 H 0.3845 0.3968 0.5673 0.021 Uiso 1 1 calc R U . . .
C14 C 0.05367(17) 0.69129(6) 0.70792(10) 0.0205(2) Uani 1 1 d . . . . .
H14 H 0.0687 0.6984 0.7852 0.025 Uiso 1 1 calc R U . . .
C10 C -0.05439(19) 0.57957(6) 0.00772(10) 0.0220(3) Uani 1 1 d . . . . .
C5 C 0.35301(19) 0.66646(7) 0.06881(10) 0.0252(3) Uani 1 1 d . . . . .
N1 N 0.49612(16) 0.70461(6) 0.10487(10) 0.0294(3) Uani 1 1 d . . . . .
C1 C 0.22549(17) 0.63786(6) 0.13332(9) 0.0187(2) Uani 1 1 d . . . . .
C9 C -0.30000(19) 0.53679(6) 0.08981(10) 0.0248(3) Uani 1 1 d . . . . .
H9 H -0.4191 0.5145 0.0842 0.030 Uiso 1 1 calc R U . . .
C3 C 0.40850(17) 0.68948(6) 0.28773(10) 0.0208(2) Uani 1 1 d . . . . .
H3 H 0.4332 0.6983 0.3643 0.025 Uiso 1 1 calc R U . . .
B1 B 0.08675(18) 0.61746(6) 0.30827(10) 0.0156(2) Uani 1 1 d . . . . .
C4 C 0.52243(18) 0.71600(6) 0.21364(11) 0.0262(3) Uani 1 1 d . . . . .
H4 H 0.6244 0.7437 0.2413 0.031 Uiso 1 1 calc R U . . .


_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
O2 C17 1.3449(13) . ?
O2 C18 1.3946(13) . ?
F1 C10 1.3488(14) . ?
F2 C5 1.3488(15) . ?
O1 C11 1.3430(13) . ?
O1 B1 1.4770(15) . ?
N3 C17 1.3178(14) . ?
N3 C23 1.4030(14) . ?
N3 B1 1.5809(15) . ?
N2 C10 1.3132(17) . ?
N2 C9 1.3458(17) . ?
C23 C18 1.3861(15) . ?
C23 C22 1.3908(15) . ?
C7 C8 1.3884(17) . ?
C7 C6 1.4070(15) . ?
C7 B1 1.6163(16) . ?
C12 C13 1.3859(17) . ?
C12 C11 1.3937(16) . ?
C12 H12 0.9500 . ?
C17 C16 1.4265(15) . ?
C18 C19 1.3796(16) . ?
C21 C22 1.3910(17) . ?
C21 C20 1.4022(17) . ?
C21 H21 0.9500 . ?
C16 C15 1.4046(15) . ?
C16 C11 1.4144(16) . ?
C13 C14 1.3981(18) . ?
C13 H13 0.9500 . ?
C20 C19 1.3924(16) . ?
C20 H20 0.9500 . ?
C6 C10 1.3919(17) . ?
C6 C1 1.4904(16) . ?
C2 C3 1.3894(17) . ?
C2 C1 1.4100(16) . ?
C2 B1 1.6215(16) . ?
C15 C14 1.3782(17) . ?
C15 H15 0.9500 . ?
C8 C9 1.3869(17) . ?
C8 H8 0.9500 . ?
C22 H22 0.9500 . ?
C19 H19 0.9500 . ?
C14 H14 0.9500 . ?
C5 N1 1.3162(18) . ?
C5 C1 1.3896(17) . ?
N1 C4 1.3420(18) . ?
C9 H9 0.9500 . ?
C3 C4 1.3868(17) . ?
C3 H3 0.9500 . ?
C4 H4 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
C17 O2 C18 105.35(8) . . ?
C11 O1 B1 124.12(9) . . ?
C17 N3 C23 107.11(9) . . ?
C17 N3 B1 121.81(9) . . ?
C23 N3 B1 131.08(9) . . ?
C10 N2 C9 117.04(11) . . ?
C18 C23 C22 121.01(11) . . ?
C18 C23 N3 106.20(9) . . ?
C22 C23 N3 132.79(10) . . ?
C8 C7 C6 119.04(10) . . ?
C8 C7 B1 131.16(10) . . ?
C6 C7 B1 109.78(10) . . ?
C13 C12 C11 119.57(11) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
N3 C17 O2 112.87(10) . . ?
N3 C17 C16 124.14(10) . . ?
O2 C17 C16 122.99(10) . . ?
C19 C18 C23 124.07(10) . . ?
C19 C18 O2 127.49(10) . . ?
C23 C18 O2 108.44(9) . . ?
C22 C21 C20 122.26(11) . . ?
C22 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
C15 C16 C11 121.16(10) . . ?
C15 C16 C17 123.09(10) . . ?
C11 C16 C17 115.73(10) . . ?
C12 C13 C14 121.89(11) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C19 C20 C21 121.68(11) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C10 C6 C7 116.22(11) . . ?
C10 C6 C1 133.12(11) . . ?
C7 C6 C1 110.58(10) . . ?
O1 C11 C12 119.37(10) . . ?
O1 C11 C16 121.92(10) . . ?
C12 C11 C16 118.56(10) . . ?
C3 C2 C1 118.99(11) . . ?
C3 C2 B1 131.02(11) . . ?
C1 C2 B1 109.67(10) . . ?
C14 C15 C16 119.37(11) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C9 C8 C7 118.91(11) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C23 C22 C21 115.92(11) . . ?
C23 C22 H22 122.0 . . ?
C21 C22 H22 122.0 . . ?
C18 C19 C20 115.05(10) . . ?
C18 C19 H19 122.5 . . ?
C20 C19 H19 122.5 . . ?
C15 C14 C13 119.42(11) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
N2 C10 F1 114.07(10) . . ?
N2 C10 C6 125.89(11) . . ?
F1 C10 C6 120.05(11) . . ?
N1 C5 F2 114.07(11) . . ?
N1 C5 C1 125.65(12) . . ?
F2 C5 C1 120.26(12) . . ?
C5 N1 C4 116.97(11) . . ?
C5 C1 C2 116.42(11) . . ?
C5 C1 C6 133.01(11) . . ?
C2 C1 C6 110.29(10) . . ?
N2 C9 C8 122.91(12) . . ?
N2 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
C4 C3 C2 118.55(12) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
O1 B1 N3 107.36(9) . . ?
O1 B1 C7 112.16(9) . . ?
N3 B1 C7 111.65(9) . . ?
O1 B1 C2 114.07(9) . . ?
N3 B1 C2 111.94(9) . . ?
C7 B1 C2 99.65(9) . . ?
N1 C4 C3 123.39(12) . . ?
N1 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

_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_3d
_database_code_depnum_ccdc_archive 'CCDC 2243654'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          290
_chemical_formula_moiety         'C23 H12 B F2 N3 O S, C H2 Cl2'
_chemical_formula_sum            'C24 H14 B Cl2 F2 N3 O S'
_chemical_formula_weight         512.15

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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      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                   7.70860(10)
_cell_length_b                   10.42680(10)
_cell_length_c                   14.8449(2)
_cell_angle_alpha                72.3950(10)
_cell_angle_beta                 76.2380(10)
_cell_angle_gamma                71.8570(10)
_cell_volume                     1067.06(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    21075
_cell_measurement_theta_min      4.6100
_cell_measurement_theta_max      77.0730

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    4.026
_exptl_absorpt_correction_T_min  0.31507
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.697
_oxdiff_exptl_absorpt_empirical_full_max 1.924
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            26231
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.606
_diffrn_reflns_theta_max         77.549
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4475
_reflns_number_gt                4368
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'

_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)+(0.0444P)²+0.5883P] 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         4475
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
S1 S 0.46744(4) 0.43510(3) 0.37061(2) 0.01804(9) Uani 1 1 d . . . . .
Cl2 Cl 0.37323(5) 1.88220(4) -0.00396(3) 0.03121(10) Uani 1 1 d . . . . .
Cl1 Cl 0.26177(6) 1.63116(4) 0.11704(3) 0.03753(11) Uani 1 1 d . . . . .
F1 F 0.45763(13) 1.29382(8) 0.19898(6) 0.0273(2) Uani 1 1 d . . . . .
F2 F 0.20229(13) 1.28882(9) 0.11291(6) 0.0289(2) Uani 1 1 d . . . . .
N3 N 0.40890(16) 0.69898(11) 0.34421(8) 0.0173(2) Uani 1 1 d . . . . .
O1 O 0.18862(15) 0.84498(10) 0.44977(8) 0.0254(2) Uani 1 1 d . . . . .
N1 N 0.03169(18) 1.14676(14) 0.11950(10) 0.0270(3) Uani 1 1 d . . . . .
C11 C 0.54607(18) 0.66482(14) 0.26787(10) 0.0180(3) Uani 1 1 d . . . . .
C23 C 0.13838(19) 0.73155(14) 0.50621(10) 0.0192(3) Uani 1 1 d . . . . .
C5 C 0.4973(2) 1.16982(14) 0.26382(10) 0.0215(3) Uani 1 1 d . . . . .
N2 N 0.62570(18) 1.15731(13) 0.31252(9) 0.0240(3) Uani 1 1 d . . . . .
C13 C 0.7628(2) 0.70155(16) 0.12460(11) 0.0232(3) Uani 1 1 d . . . . .
H13 H 0.8218 0.7618 0.0735 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5832(2) 0.93158(15) 0.39891(10) 0.0225(3) Uani 1 1 d . . . . .
H3 H 0.6166 0.8489 0.4474 0.027 Uiso 1 1 calc R U . . .
C18 C 0.21785(18) 0.59909(14) 0.48749(10) 0.0178(3) Uani 1 1 d . . . . .
C17 C 0.35587(18) 0.58911(13) 0.40325(10) 0.0167(3) Uani 1 1 d . . . . .
C20 C 0.0399(2) 0.49600(15) 0.63381(10) 0.0226(3) Uani 1 1 d . . . . .
H20 H 0.0068 0.4165 0.6777 0.027 Uiso 1 1 calc R U . . .
C16 C 0.59524(18) 0.52235(14) 0.27152(10) 0.0178(3) Uani 1 1 d . . . . .
C2 C 0.44793(19) 0.94734(14) 0.34633(10) 0.0191(3) Uani 1 1 d . . . . .
C12 C 0.6294(2) 0.75603(14) 0.19364(10) 0.0213(3) Uani 1 1 d . . . . .
H12 H 0.5957 0.8528 0.1905 0.026 Uiso 1 1 calc R U . . .
C19 C 0.16716(19) 0.48236(14) 0.55204(10) 0.0203(3) Uani 1 1 d . . . . .
H19 H 0.2209 0.3930 0.5394 0.024 Uiso 1 1 calc R U . . .
C15 C 0.72990(19) 0.46730(15) 0.20189(10) 0.0209(3) Uani 1 1 d . . . . .
H15 H 0.7636 0.3706 0.2046 0.025 Uiso 1 1 calc R U . . .
C22 C 0.0073(2) 0.74454(15) 0.58857(10) 0.0226(3) Uani 1 1 d . . . . .
H22 H -0.0491 0.8336 0.6012 0.027 Uiso 1 1 calc R U . . .
C1 C 0.40169(19) 1.07173(14) 0.27514(10) 0.0191(3) Uani 1 1 d . . . . .
C4 C 0.6693(2) 1.03797(15) 0.37993(11) 0.0242(3) Uani 1 1 d . . . . .
H4 H 0.7625 1.0260 0.4159 0.029 Uiso 1 1 calc R U . . .
C10 C 0.19851(19) 0.94519(14) 0.26810(10) 0.0202(3) Uani 1 1 d . . . . .
C6 C 0.25286(19) 1.07013(14) 0.22748(10) 0.0197(3) Uani 1 1 d . . . . .
C8 C -0.0160(2) 1.02591(17) 0.15791(12) 0.0283(3) Uani 1 1 d . . . . .
H8 H -0.1080 1.0098 0.1331 0.034 Uiso 1 1 calc R U . . .
C7 C 0.1615(2) 1.16491(14) 0.15437(10) 0.0228(3) Uani 1 1 d . . . . .
C21 C -0.0399(2) 0.62806(16) 0.65136(10) 0.0226(3) Uani 1 1 d . . . . .
H21 H -0.1280 0.6378 0.7074 0.027 Uiso 1 1 calc R U . . .
C14 C 0.8122(2) 0.55854(16) 0.12897(11) 0.0233(3) Uani 1 1 d . . . . .
H14 H 0.9043 0.5238 0.0807 0.028 Uiso 1 1 calc R U . . .
C9 C 0.0625(2) 0.92334(16) 0.23214(11) 0.0250(3) Uani 1 1 d . . . . .
H9 H 0.0239 0.8396 0.2579 0.030 Uiso 1 1 calc R U . . .
B1 B 0.3099(2) 0.85200(16) 0.35606(11) 0.0194(3) Uani 1 1 d . . . . .
C24 C 0.3588(3) 1.71341(18) 0.00226(13) 0.0353(4) Uani 1 1 d . . . . .
H24A H 0.2825 1.7204 -0.0449 0.042 Uiso 1 1 calc R U . . .
H24B H 0.4843 1.6554 -0.0152 0.042 Uiso 1 1 calc R U . . .


_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
S1 C17 1.7220(13) . ?
S1 C16 1.7381(14) . ?
Cl2 C24 1.7712(17) . ?
Cl1 C24 1.7628(18) . ?
F1 C5 1.3538(16) . ?
F2 C7 1.3515(17) . ?
N3 C17 1.3272(18) . ?
N3 C11 1.4031(17) . ?
N3 B1 1.5833(17) . ?
O1 C23 1.3350(17) . ?
O1 B1 1.4752(18) . ?
N1 C7 1.315(2) . ?
N1 C8 1.343(2) . ?
C11 C12 1.393(2) . ?
C11 C16 1.4013(18) . ?
C23 C22 1.400(2) . ?
C23 C18 1.4087(19) . ?
C5 N2 1.312(2) . ?
C5 C1 1.387(2) . ?
N2 C4 1.345(2) . ?
C13 C12 1.385(2) . ?
C13 C14 1.404(2) . ?
C13 H13 0.9500 . ?
C3 C2 1.388(2) . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C18 C19 1.4017(19) . ?
C18 C17 1.4434(19) . ?
C20 C19 1.381(2) . ?
C20 C21 1.398(2) . ?
C20 H20 0.9500 . ?
C16 C15 1.3974(19) . ?
C2 C1 1.4101(19) . ?
C2 B1 1.625(2) . ?
C12 H12 0.9500 . ?
C19 H19 0.9500 . ?
C15 C14 1.381(2) . ?
C15 H15 0.9500 . ?
C22 C21 1.381(2) . ?
C22 H22 0.9500 . ?
C1 C6 1.491(2) . ?
C4 H4 0.9500 . ?
C10 C9 1.387(2) . ?
C10 C6 1.407(2) . ?
C10 B1 1.623(2) . ?
C6 C7 1.390(2) . ?
C8 C9 1.388(2) . ?
C8 H8 0.9500 . ?
C21 H21 0.9500 . ?
C14 H14 0.9500 . ?
C9 H9 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 S1 C16 90.32(6) . . ?
C17 N3 C11 112.76(11) . . ?
C17 N3 B1 121.78(11) . . ?
C11 N3 B1 125.21(11) . . ?
C23 O1 B1 125.25(11) . . ?
C7 N1 C8 116.95(13) . . ?
C12 C11 C16 120.62(12) . . ?
C12 C11 N3 126.89(12) . . ?
C16 C11 N3 112.49(12) . . ?
O1 C23 C22 118.58(12) . . ?
O1 C23 C18 122.17(12) . . ?
C22 C23 C18 119.21(13) . . ?
N2 C5 F1 113.73(12) . . ?
N2 C5 C1 126.29(14) . . ?
F1 C5 C1 119.96(13) . . ?
C5 N2 C4 117.08(13) . . ?
C12 C13 C14 120.99(14) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C2 C3 C4 119.35(14) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C19 C18 C23 119.71(12) . . ?
C19 C18 C17 122.57(12) . . ?
C23 C18 C17 117.67(12) . . ?
N3 C17 C18 122.48(12) . . ?
N3 C17 S1 114.00(10) . . ?
C18 C17 S1 123.51(10) . . ?
C19 C20 C21 119.32(13) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C15 C16 C11 121.30(13) . . ?
C15 C16 S1 128.27(11) . . ?
C11 C16 S1 110.43(10) . . ?
C3 C2 C1 118.70(13) . . ?
C3 C2 B1 131.88(13) . . ?
C1 C2 B1 109.17(12) . . ?
C13 C12 C11 118.11(13) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C20 C19 C18 120.62(13) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C14 C15 C16 117.57(13) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 H15 121.2 . . ?
C21 C22 C23 120.08(13) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C5 C1 C2 116.14(13) . . ?
C5 C1 C6 132.96(13) . . ?
C2 C1 C6 110.89(12) . . ?
N2 C4 C3 122.45(14) . . ?
N2 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C9 C10 C6 118.81(13) . . ?
C9 C10 B1 131.35(13) . . ?
C6 C10 B1 109.79(12) . . ?
C7 C6 C10 116.57(13) . . ?
C7 C6 C1 133.21(13) . . ?
C10 C6 C1 110.22(12) . . ?
N1 C8 C9 123.16(14) . . ?
N1 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
N1 C7 F2 113.93(13) . . ?
N1 C7 C6 125.67(14) . . ?
F2 C7 C6 120.40(13) . . ?
C22 C21 C20 121.04(13) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C15 C14 C13 121.41(13) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C10 C9 C8 118.83(14) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
O1 B1 N3 109.25(11) . . ?
O1 B1 C10 112.21(12) . . ?
N3 B1 C10 111.49(11) . . ?
O1 B1 C2 108.89(11) . . ?
N3 B1 C2 115.18(11) . . ?
C10 B1 C2 99.58(11) . . ?
Cl1 C24 Cl2 112.54(10) . . ?
Cl1 C24 H24A 109.1 . . ?
Cl2 C24 H24A 109.1 . . ?
Cl1 C24 H24B 109.1 . . ?
Cl2 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

_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_6c
_database_code_depnum_ccdc_archive 'CCDC 2243657'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          323
_chemical_formula_moiety         'C23 H10 B F4 N3 O2'
_chemical_formula_sum            'C23 H10 B F4 N3 O2'
_chemical_formula_weight         447.15

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'
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'
B B 0.0013 0.0007 '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                   10.5464(7)
_cell_length_b                   14.5142(4)
_cell_length_c                   12.4614(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.766(11)
_cell_angle_gamma                90
_cell_volume                     1906.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7719
_cell_measurement_theta_min      3.2550
_cell_measurement_theta_max      30.6550

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.127
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.133
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 2 -3 0.1263
0 -5 -1 0.1023
0 5 1 0.1038
1 -5 0 0.1257
2 2 3 0.2333
-1 0 2 0.0657
5 -3 -8 0.0820
2 2 -7 0.0995
1 -1 -1 0.1031
-1 1 1 0.1056
1 0 -2 0.0675
3 5 -4 0.0849
-5 -5 4 0.1103
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9980 1.9828 -3.0036 -0.0568 -0.1672 0.2825
0.0127 -5.0051 -1.0127 -0.0321 -0.1986 -0.1502
-0.0127 5.0051 1.0127 0.0321 0.1986 0.1502
1.0101 -4.9964 -0.0092 -0.0203 -0.0995 -0.2396
1.9888 2.0201 3.0128 0.0562 0.2984 -0.1375
-1.0011 -0.0043 2.0001 0.0866 0.0047 -0.0039
5.0099 -2.9778 -8.0050 -0.3670 -0.0527 -0.1515
2.0014 2.0058 -6.9992 -0.2720 -0.0476 0.1736
1.0021 -0.9950 -1.0012 -0.0537 -0.0029 -0.0635
-1.0021 0.9950 1.0012 0.0537 0.0029 0.0635
1.0011 0.0043 -2.0001 -0.0866 -0.0047 0.0039
2.9893 5.0194 -3.9864 -0.1949 0.2191 0.1308
-4.9865 -5.0338 3.9818 0.2368 -0.3481 -0.0141
_exptl_absorpt_correction_T_min  0.451
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.860
_oxdiff_exptl_absorpt_empirical_full_max 1.105
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            14484
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.249
_diffrn_reflns_theta_max         30.737
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5117
_reflns_number_gt                4097
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'

_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)+(0.0591P)²+0.4387P] 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         5117
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
O2 O 0.37727(8) 0.09237(6) 0.43836(7) 0.01855(19) Uani 1 1 d . . . . .
O1 O 0.04602(9) 0.23002(7) 0.36185(7) 0.0228(2) Uani 1 1 d . . . . .
F1 F 0.05239(9) 0.26177(7) -0.10614(6) 0.0359(2) Uani 1 1 d . . . . .
N3 N 0.22672(10) 0.13069(7) 0.31828(8) 0.0169(2) Uani 1 1 d . . . . .
F3 F 0.34021(9) 0.43707(6) 0.06997(8) 0.0409(2) Uani 1 1 d . . . . .
F2 F -0.10289(9) 0.12610(7) -0.07369(7) 0.0396(2) Uani 1 1 d . . . . .
F4 F -0.19790(9) -0.07644(7) 0.18163(9) 0.0443(3) Uani 1 1 d . . . . .
C23 C 0.09424(12) 0.23726(8) 0.46214(10) 0.0185(2) Uani 1 1 d . . . . .
C19 C 0.25793(13) 0.20640(9) 0.60144(10) 0.0206(3) Uani 1 1 d . . . . .
H19 H 0.3358 0.1781 0.6229 0.025 Uiso 1 1 calc R U . . .
C16 C 0.40462(12) 0.04872(8) 0.34166(9) 0.0175(2) Uani 1 1 d . . . . .
C12 C 0.31111(12) 0.03667(9) 0.16245(10) 0.0192(2) Uani 1 1 d . . . . .
H12 H 0.2470 0.0517 0.1102 0.023 Uiso 1 1 calc R U . . .
N1 N 0.19466(13) 0.34805(8) -0.01483(10) 0.0304(3) Uani 1 1 d . . . . .
C17 C 0.26982(11) 0.14005(8) 0.41748(9) 0.0165(2) Uani 1 1 d . . . . .
C21 C 0.07686(13) 0.29861(9) 0.64077(10) 0.0238(3) Uani 1 1 d . . . . .
H21 H 0.0310 0.3337 0.6909 0.029 Uiso 1 1 calc R U . . .
N2 N -0.14852(11) 0.02755(9) 0.05724(11) 0.0315(3) Uani 1 1 d . . . . .
C22 C 0.02751(13) 0.28818(9) 0.53758(10) 0.0218(3) Uani 1 1 d . . . . .
H22 H -0.0516 0.3155 0.5177 0.026 Uiso 1 1 calc R U . . .
C1 C 0.00062(12) 0.14900(9) 0.09653(10) 0.0211(3) Uani 1 1 d . . . . .
C11 C 0.31029(11) 0.07155(8) 0.26621(10) 0.0168(2) Uani 1 1 d . . . . .
C15 C 0.50638(12) -0.00714(9) 0.32064(10) 0.0207(3) Uani 1 1 d . . . . .
H15 H 0.5713 -0.0204 0.3729 0.025 Uiso 1 1 calc R U . . .
C2 C 0.01150(12) 0.11842(9) 0.20403(10) 0.0201(3) Uani 1 1 d . . . . .
C18 C 0.20937(12) 0.19489(8) 0.49628(9) 0.0180(2) Uani 1 1 d . . . . .
C7 C 0.15208(12) 0.25315(9) 0.17537(10) 0.0193(3) Uani 1 1 d . . . . .
C13 C 0.41106(12) -0.02145(9) 0.13969(10) 0.0216(3) Uani 1 1 d . . . . .
H13 H 0.4149 -0.0476 0.0700 0.026 Uiso 1 1 calc R U . . .
C6 C 0.08528(12) 0.22873(9) 0.07920(10) 0.0207(3) Uani 1 1 d . . . . .
C14 C 0.50683(13) -0.04284(9) 0.21658(11) 0.0225(3) Uani 1 1 d . . . . .
H14 H 0.5738 -0.0827 0.1972 0.027 Uiso 1 1 calc R U . . .
C8 C 0.24075(13) 0.32361(9) 0.17373(11) 0.0237(3) Uani 1 1 d . . . . .
H8 H 0.2886 0.3413 0.2362 0.028 Uiso 1 1 calc R U . . .
C20 C 0.19269(14) 0.25879(9) 0.67357(11) 0.0242(3) Uani 1 1 d . . . . .
H20 H 0.2258 0.2678 0.7446 0.029 Uiso 1 1 calc R U . . .
C5 C -0.08292(13) 0.10075(10) 0.02924(11) 0.0271(3) Uani 1 1 d . . . . .
C10 C 0.11205(14) 0.27981(10) -0.01159(11) 0.0263(3) Uani 1 1 d . . . . .
C3 C -0.05762(13) 0.04251(10) 0.23571(12) 0.0263(3) Uani 1 1 d . . . . .
H3 H -0.0536 0.0205 0.3075 0.032 Uiso 1 1 calc R U . . .
C4 C -0.13293(13) 0.00044(10) 0.15707(13) 0.0300(3) Uani 1 1 d . . . . .
C9 C 0.25558(14) 0.36680(9) 0.07582(12) 0.0288(3) Uani 1 1 d . . . . .
B1 B 0.10853(13) 0.18463(10) 0.27149(11) 0.0182(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
O2 C17 1.3464(14) . ?
O2 C16 1.3993(14) . ?
O1 C23 1.3388(15) . ?
O1 B1 1.4772(16) . ?
F1 C10 1.3442(16) . ?
N3 C17 1.3109(15) . ?
N3 C11 1.4035(15) . ?
N3 B1 1.5690(17) . ?
F3 C9 1.3587(17) . ?
F2 C5 1.3447(16) . ?
F4 C4 1.3495(17) . ?
C23 C22 1.4022(17) . ?
C23 C18 1.4148(18) . ?
C19 C20 1.3776(18) . ?
C19 C18 1.4022(17) . ?
C19 H19 0.9500 . ?
C16 C15 1.3766(17) . ?
C16 C11 1.3877(17) . ?
C12 C13 1.3862(17) . ?
C12 C11 1.3888(17) . ?
C12 H12 0.9500 . ?
N1 C9 1.311(2) . ?
N1 C10 1.320(2) . ?
C17 C18 1.4293(17) . ?
C21 C22 1.3807(19) . ?
C21 C20 1.401(2) . ?
C21 H21 0.9500 . ?
N2 C4 1.310(2) . ?
N2 C5 1.321(2) . ?
C22 H22 0.9500 . ?
C1 C5 1.3871(18) . ?
C1 C2 1.4125(18) . ?
C1 C6 1.481(2) . ?
C15 C14 1.3966(19) . ?
C15 H15 0.9500 . ?
C2 C3 1.3853(19) . ?
C2 B1 1.6200(19) . ?
C7 C8 1.3864(19) . ?
C7 C6 1.4163(17) . ?
C7 B1 1.6336(19) . ?
C13 C14 1.4053(18) . ?
C13 H13 0.9500 . ?
C6 C10 1.3889(18) . ?
C14 H14 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C20 H20 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3 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
C17 O2 C16 105.12(9) . . ?
C23 O1 B1 125.51(10) . . ?
C17 N3 C11 107.15(10) . . ?
C17 N3 B1 123.17(10) . . ?
C11 N3 B1 129.52(10) . . ?
O1 C23 C22 118.89(11) . . ?
O1 C23 C18 122.98(11) . . ?
C22 C23 C18 118.12(11) . . ?
C20 C19 C18 120.01(12) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C15 C16 C11 123.95(11) . . ?
C15 C16 O2 127.81(11) . . ?
C11 C16 O2 108.24(10) . . ?
C13 C12 C11 116.04(12) . . ?
C13 C12 H12 122.0 . . ?
C11 C12 H12 122.0 . . ?
C9 N1 C10 115.84(12) . . ?
N3 C17 O2 113.23(10) . . ?
N3 C17 C18 123.82(11) . . ?
O2 C17 C18 122.96(11) . . ?
C22 C21 C20 121.79(12) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C4 N2 C5 116.17(12) . . ?
C21 C22 C23 119.97(12) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C5 C1 C2 116.50(13) . . ?
C5 C1 C6 132.90(13) . . ?
C2 C1 C6 110.60(11) . . ?
C16 C11 C12 121.25(11) . . ?
C16 C11 N3 106.26(10) . . ?
C12 C11 N3 132.48(11) . . ?
C16 C15 C14 114.85(12) . . ?
C16 C15 H15 122.6 . . ?
C14 C15 H15 122.6 . . ?
C3 C2 C1 119.48(12) . . ?
C3 C2 B1 130.80(12) . . ?
C1 C2 B1 109.72(11) . . ?
C19 C18 C23 120.97(11) . . ?
C19 C18 C17 123.41(11) . . ?
C23 C18 C17 115.61(11) . . ?
C8 C7 C6 119.36(12) . . ?
C8 C7 B1 131.67(12) . . ?
C6 C7 B1 108.93(11) . . ?
C12 C13 C14 122.00(12) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C10 C6 C7 116.57(13) . . ?
C10 C6 C1 132.39(13) . . ?
C7 C6 C1 111.00(11) . . ?
C15 C14 C13 121.88(12) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C7 C8 C9 116.19(13) . . ?
C7 C8 H8 121.9 . . ?
C9 C8 H8 121.9 . . ?
C19 C20 C21 119.08(12) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
N2 C5 F2 113.84(12) . . ?
N2 C5 C1 125.07(13) . . ?
F2 C5 C1 121.09(14) . . ?
N1 C10 F1 114.25(12) . . ?
N1 C10 C6 125.17(13) . . ?
F1 C10 C6 120.57(14) . . ?
C2 C3 C4 116.39(13) . . ?
C2 C3 H3 121.8 . . ?
C4 C3 H3 121.8 . . ?
N2 C4 F4 114.45(13) . . ?
N2 C4 C3 126.31(14) . . ?
F4 C4 C3 119.24(14) . . ?
N1 C9 F3 114.52(13) . . ?
N1 C9 C8 126.84(14) . . ?
F3 C9 C8 118.64(14) . . ?
O1 B1 N3 107.90(10) . . ?
O1 B1 C2 111.74(10) . . ?
N3 B1 C2 112.26(10) . . ?
O1 B1 C7 115.44(11) . . ?
N3 B1 C7 109.76(10) . . ?
C2 B1 C7 99.67(10) . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4


_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_3f
_database_code_depnum_ccdc_archive 'CCDC 2243656'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          309
_chemical_formula_moiety         'C21 H12 B F2 N3 O'
_chemical_formula_sum            'C21 H12 B F2 N3 O'
_chemical_formula_weight         371.15

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'
O O 0.0492 0.0322 '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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   18.0134(2)
_cell_length_b                   8.61830(10)
_cell_length_c                   11.09470(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.9080(10)
_cell_angle_gamma                90
_cell_volume                     1574.61(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6741
_cell_measurement_theta_min      5.3620
_cell_measurement_theta_max      76.8230

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_T_min  0.70136
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.695
_oxdiff_exptl_absorpt_empirical_full_max 1.340
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            8250
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.372
_diffrn_reflns_theta_max         78.009
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_point_group_measured_fraction_full 0.846
_reflns_number_total             2714
_reflns_number_gt                2686
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_max     0.634
_reflns_Friedel_fraction_full    0.691

_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'

_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)+(0.0510P)²+0.9732P] 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     SHELXL
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2714
_refine_ls_number_parameters     254
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.01759(9) 0.07377(19) 0.44638(15) 0.0246(4) Uani 1 1 d . . . . .
C15 C -0.00829(14) 0.2931(3) -0.1615(2) 0.0145(5) Uani 1 1 d . . . . .
F2 F -0.11948(9) 0.21266(18) 0.38169(15) 0.0232(4) Uani 1 1 d . . . . .
C14 C -0.03496(15) 0.2206(3) -0.2843(3) 0.0177(5) Uani 1 1 d . . . . .
H14 H -0.0035 0.2279 -0.3352 0.021 Uiso 1 1 calc R U . . .
C16 C 0.06664(14) 0.3850(3) -0.1049(2) 0.0148(5) Uani 1 1 d . . . . .
N3 N -0.05521(12) 0.2862(2) -0.0914(2) 0.0143(4) Uani 1 1 d . . . . .
O1 O 0.01724(10) 0.51326(19) 0.03927(17) 0.0154(4) Uani 1 1 d . . . . .
C6 C -0.07363(13) 0.2971(3) 0.2192(2) 0.0139(5) Uani 1 1 d . . . . .
C21 C 0.07423(14) 0.4990(3) -0.0103(2) 0.0141(5) Uani 1 1 d . . . . .
C10 C -0.09067(14) 0.3905(3) 0.1065(2) 0.0144(5) Uani 1 1 d . . . . .
C20 C 0.13981(15) 0.6015(3) 0.0303(2) 0.0166(5) Uani 1 1 d . . . . .
H20 H 0.1436 0.6823 0.0907 0.020 Uiso 1 1 calc R U . . .
C19 C 0.19950(14) 0.5849(3) -0.0180(2) 0.0185(5) Uani 1 1 d . . . . .
H19 H 0.2436 0.6558 0.0089 0.022 Uiso 1 1 calc R U . . .
C9 C -0.16046(14) 0.4813(3) 0.0615(2) 0.0167(5) Uani 1 1 d . . . . .
H9 H -0.1732 0.5464 -0.0133 0.020 Uiso 1 1 calc R U . . .
N1 N 0.11313(13) 0.0362(2) 0.3697(2) 0.0194(4) Uani 1 1 d . . . . .
C8 C -0.21140(14) 0.4750(3) 0.1279(3) 0.0179(5) Uani 1 1 d . . . . .
H8 H -0.2591 0.5369 0.0965 0.021 Uiso 1 1 calc R U . . .
C7 C -0.12972(15) 0.3017(3) 0.2754(2) 0.0168(5) Uani 1 1 d . . . . .
C1 C 0.00367(15) 0.2105(3) 0.2525(3) 0.0150(5) Uani 1 1 d . . . . .
N2 N -0.19624(12) 0.3855(3) 0.2344(2) 0.0184(4) Uani 1 1 d . . . . .
C17 C 0.12875(15) 0.3672(3) -0.1494(2) 0.0175(5) Uani 1 1 d . . . . .
H17 H 0.1251 0.2869 -0.2102 0.021 Uiso 1 1 calc R U . . .
C12 C -0.15399(15) 0.1322(3) -0.2590(3) 0.0191(5) Uani 1 1 d . . . . .
H12 H -0.2039 0.0770 -0.2906 0.023 Uiso 1 1 calc R U . . .
C2 C 0.03725(14) 0.2441(3) 0.1611(2) 0.0151(5) Uani 1 1 d . . . . .
C13 C -0.10664(15) 0.1384(3) -0.3320(3) 0.0191(5) Uani 1 1 d . . . . .
H13 H -0.1238 0.0861 -0.4142 0.023 Uiso 1 1 calc R U . . .
C4 C 0.14450(14) 0.0671(3) 0.2810(3) 0.0205(5) Uani 1 1 d . . . . .
H4 H 0.1934 0.0165 0.2905 0.025 Uiso 1 1 calc R U . . .
C11 C -0.12602(15) 0.2085(3) -0.1397(3) 0.0177(5) Uani 1 1 d . . . . .
H11 H -0.1580 0.2061 -0.0895 0.021 Uiso 1 1 calc R U . . .
B1 B -0.02087(16) 0.3672(3) 0.0520(3) 0.0151(5) Uani 1 1 d . . . . .
C5 C 0.04557(15) 0.1081(3) 0.3537(2) 0.0172(5) Uani 1 1 d . . . . .
C18 C 0.19550(15) 0.4656(3) -0.1054(3) 0.0185(5) Uani 1 1 d . . . . .
H18 H 0.2380 0.4518 -0.1344 0.022 Uiso 1 1 calc R U . . .
C3 C 0.10936(14) 0.1685(3) 0.1769(2) 0.0171(5) Uani 1 1 d . . . . .
H3 H 0.1338 0.1867 0.1167 0.021 Uiso 1 1 calc R U . . .


_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 C5 1.349(3) . ?
C15 N3 1.363(3) . ?
C15 C14 1.396(3) . ?
C15 C16 1.468(3) . ?
F2 C7 1.355(3) . ?
C14 C13 1.377(3) . ?
C14 H14 0.9500 . ?
C16 C17 1.402(3) . ?
C16 C21 1.404(3) . ?
N3 C11 1.345(3) . ?
N3 B1 1.613(3) . ?
O1 C21 1.352(3) . ?
O1 B1 1.468(3) . ?
C6 C7 1.386(3) . ?
C6 C10 1.412(3) . ?
C6 C1 1.489(3) . ?
C21 C20 1.395(3) . ?
C10 C9 1.390(3) . ?
C10 B1 1.614(3) . ?
C20 C19 1.389(4) . ?
C20 H20 0.9500 . ?
C19 C18 1.395(4) . ?
C19 H19 0.9500 . ?
C9 C8 1.392(4) . ?
C9 H9 0.9500 . ?
N1 C5 1.312(3) . ?
N1 C4 1.345(4) . ?
C8 N2 1.343(4) . ?
C8 H8 0.9500 . ?
C7 N2 1.313(3) . ?
C1 C5 1.386(3) . ?
C1 C2 1.406(4) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C12 C11 1.378(4) . ?
C12 C13 1.395(4) . ?
C12 H12 0.9500 . ?
C2 C3 1.399(3) . ?
C2 B1 1.630(4) . ?
C13 H13 0.9500 . ?
C4 C3 1.381(4) . ?
C4 H4 0.9500 . ?
C11 H11 0.9500 . ?
C18 H18 0.9500 . ?
C3 H3 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
N3 C15 C14 119.3(2) . . ?
N3 C15 C16 117.1(2) . . ?
C14 C15 C16 123.5(2) . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C17 C16 C21 119.3(2) . . ?
C17 C16 C15 121.1(2) . . ?
C21 C16 C15 119.4(2) . . ?
C11 N3 C15 120.1(2) . . ?
C11 N3 B1 122.1(2) . . ?
C15 N3 B1 117.73(19) . . ?
C21 O1 B1 115.00(18) . . ?
C7 C6 C10 116.4(2) . . ?
C7 C6 C1 133.0(2) . . ?
C10 C6 C1 110.6(2) . . ?
O1 C21 C20 119.6(2) . . ?
O1 C21 C16 120.5(2) . . ?
C20 C21 C16 119.8(2) . . ?
C9 C10 C6 118.7(2) . . ?
C9 C10 B1 131.6(2) . . ?
C6 C10 B1 109.7(2) . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C5 N1 C4 116.7(2) . . ?
N2 C8 C9 123.1(2) . . ?
N2 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?
N2 C7 F2 113.3(2) . . ?
N2 C7 C6 126.1(2) . . ?
F2 C7 C6 120.6(2) . . ?
C5 C1 C2 117.6(2) . . ?
C5 C1 C6 131.9(2) . . ?
C2 C1 C6 110.5(2) . . ?
C7 N2 C8 116.9(2) . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C11 C12 C13 117.9(2) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 B1 132.8(2) . . ?
C1 C2 B1 109.6(2) . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N1 C4 C3 123.5(2) . . ?
N1 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
N3 C11 C12 122.6(2) . . ?
N3 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
O1 B1 N3 106.5(2) . . ?
O1 B1 C10 113.3(2) . . ?
N3 B1 C10 112.20(19) . . ?
O1 B1 C2 116.4(2) . . ?
N3 B1 C2 108.95(18) . . ?
C10 B1 C2 99.57(19) . . ?
N1 C5 F1 113.9(2) . . ?
N1 C5 C1 125.5(2) . . ?
F1 C5 C1 120.5(2) . . ?
C17 C18 C19 119.2(2) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

_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_3b
_database_code_depnum_ccdc_archive 'CCDC 2243652'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          250
_chemical_formula_moiety         'C23 H14 B F2 N3 O'
_chemical_formula_sum            'C23 H14 B F2 N3 O'
_chemical_formula_weight         397.18

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_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                   13.6135(2)
_cell_length_b                   6.83220(10)
_cell_length_c                   20.0023(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.4790(10)
_cell_angle_gamma                90
_cell_volume                     1844.59(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9106
_cell_measurement_theta_min      4.4490
_cell_measurement_theta_max      77.3070

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.854
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.069
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 3 0.0639
5 0 -3 0.0676
2 -2 -1 0.1610
-2 4 1 0.1372
0 0 -1 0.0231
0 0 1 0.0456
0 -1 5 0.1139
3 0 5 0.0694
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.9970 0.0045 2.9858 -0.1062 -0.5728 -0.0749
4.9970 -0.0045 -2.9858 0.1062 0.5728 0.0749
1.9972 -2.0027 -0.9464 0.0256 0.1689 0.4771
-1.9958 4.0042 0.8985 -0.0242 -0.1101 -0.9244
0.0010 -0.0027 -1.0003 0.0774 0.0070 0.0011
-0.0010 0.0027 1.0003 -0.0774 -0.0070 -0.0011
-0.0055 -0.9870 5.0256 -0.3875 -0.0645 0.2180
2.9917 0.0160 5.0107 -0.4623 0.2960 0.0372
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.800
_oxdiff_exptl_absorpt_empirical_full_max 1.530
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            15449
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.459
_diffrn_reflns_theta_max         77.614
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3888
_reflns_number_gt                3431
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'

_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)+(0.0672P)²+0.5365P] 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         3888
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.21686(6) 0.91901(13) 0.13370(4) 0.0322(2) Uani 1 1 d . . . . .
F2 F 0.11030(7) 0.60222(14) 0.11723(4) 0.0367(2) Uani 1 1 d . . . . .
O1 O 0.38838(6) 0.54710(13) -0.07853(4) 0.0225(2) Uani 1 1 d . . . . .
N3 N 0.24284(7) 0.68229(15) -0.15258(5) 0.0197(2) Uani 1 1 d . . . . .
N2 N 0.31782(8) 1.09606(17) 0.07783(6) 0.0276(2) Uani 1 1 d . . . . .
N1 N 0.08639(8) 0.34808(18) 0.04672(6) 0.0285(3) Uani 1 1 d . . . . .
C4 C 0.10356(9) 0.2571(2) -0.00991(7) 0.0271(3) Uani 1 1 d . . . . .
H4 H 0.0715 0.1356 -0.0207 0.033 Uiso 1 1 calc R U . . .
C7 C 0.30243(9) 0.82547(19) -0.02770(6) 0.0211(3) Uani 1 1 d . . . . .
C18 C 0.34642(9) 0.43614(18) -0.19207(6) 0.0209(2) Uani 1 1 d . . . . .
C1 C 0.19524(9) 0.60674(19) 0.02091(6) 0.0218(3) Uani 1 1 d . . . . .
C2 C 0.21320(9) 0.50817(19) -0.03821(6) 0.0212(3) Uani 1 1 d . . . . .
C6 C 0.24999(9) 0.79552(19) 0.02781(6) 0.0220(3) Uani 1 1 d . . . . .
C23 C 0.40757(9) 0.43295(18) -0.12926(6) 0.0208(2) Uani 1 1 d . . . . .
C16 C 0.18558(9) 0.97048(19) -0.21848(6) 0.0234(3) Uani 1 1 d . . . . .
H16 H 0.2439 0.9649 -0.2399 0.028 Uiso 1 1 calc R U . . .
C11 C 0.17075(8) 0.83523(18) -0.16890(6) 0.0205(2) Uani 1 1 d . . . . .
C9 C 0.36694(10) 1.1223(2) 0.02451(7) 0.0272(3) Uani 1 1 d . . . . .
H9 H 0.4071 1.2356 0.0232 0.033 Uiso 1 1 calc R U . . .
C3 C 0.16569(9) 0.33066(19) -0.05375(7) 0.0243(3) Uani 1 1 d . . . . .
H3 H 0.1755 0.2612 -0.0935 0.029 Uiso 1 1 calc R U . . .
C19 C 0.36809(9) 0.31651(19) -0.24547(6) 0.0228(3) Uani 1 1 d . . . . .
H19 H 0.3265 0.3193 -0.2875 0.027 Uiso 1 1 calc R U . . .
C17 C 0.26852(9) 0.57805(18) -0.20175(6) 0.0205(2) Uani 1 1 d . . . . .
H17 H 0.2343 0.5967 -0.2458 0.025 Uiso 1 1 calc R U . . .
C10 C 0.26243(9) 0.9381(2) 0.07746(6) 0.0245(3) Uani 1 1 d . . . . .
C5 C 0.13147(9) 0.5162(2) 0.06020(6) 0.0256(3) Uani 1 1 d . . . . .
C22 C 0.49230(9) 0.3147(2) -0.12198(6) 0.0250(3) Uani 1 1 d . . . . .
H22 H 0.5362 0.3153 -0.0810 0.030 Uiso 1 1 calc R U . . .
C20 C 0.44960(10) 0.1953(2) -0.23688(7) 0.0262(3) Uani 1 1 d . . . . .
H20 H 0.4637 0.1116 -0.2723 0.031 Uiso 1 1 calc R U . . .
C15 C 0.11477(10) 1.11383(19) -0.23659(7) 0.0261(3) Uani 1 1 d . . . . .
H15 H 0.1241 1.2057 -0.2708 0.031 Uiso 1 1 calc R U . . .
C12 C 0.08606(9) 0.84162(19) -0.13671(6) 0.0223(3) Uani 1 1 d . . . . .
H12 H 0.0763 0.7487 -0.1029 0.027 Uiso 1 1 calc R U . . .
C13 C 0.01609(9) 0.9867(2) -0.15511(6) 0.0247(3) Uani 1 1 d . . . . .
H13 H -0.0421 0.9928 -0.1336 0.030 Uiso 1 1 calc R U . . .
C14 C 0.03015(9) 1.1227(2) -0.20451(7) 0.0258(3) Uani 1 1 d . . . . .
H14 H -0.0180 1.2217 -0.2164 0.031 Uiso 1 1 calc R U . . .
C21 C 0.51156(10) 0.1971(2) -0.17505(7) 0.0276(3) Uani 1 1 d . . . . .
H21 H 0.5684 0.1152 -0.1695 0.033 Uiso 1 1 calc R U . . .
C8 C 0.36145(9) 0.9907(2) -0.02871(7) 0.0250(3) Uani 1 1 d . . . . .
H8 H 0.3977 1.0136 -0.0654 0.030 Uiso 1 1 calc R U . . .
B1 B 0.28932(10) 0.6367(2) -0.07662(7) 0.0205(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.3599(14) . ?
F2 C5 1.3474(15) . ?
O1 C23 1.3324(15) . ?
O1 B1 1.4861(15) . ?
N3 C17 1.2986(16) . ?
N3 C11 1.4416(15) . ?
N3 B1 1.5986(16) . ?
N2 C10 1.3160(18) . ?
N2 C9 1.3425(18) . ?
N1 C5 1.3137(18) . ?
N1 C4 1.3392(18) . ?
C4 C3 1.3892(18) . ?
C4 H4 0.9500 . ?
C7 C8 1.3876(18) . ?
C7 C6 1.4110(16) . ?
C7 B1 1.6145(18) . ?
C18 C19 1.4065(17) . ?
C18 C23 1.4139(17) . ?
C18 C17 1.4313(16) . ?
C1 C5 1.3897(18) . ?
C1 C2 1.4096(17) . ?
C1 C6 1.4871(17) . ?
C2 C3 1.3905(18) . ?
C2 B1 1.6257(18) . ?
C6 C10 1.3856(18) . ?
C23 C22 1.4002(17) . ?
C16 C11 1.3894(18) . ?
C16 C15 1.3888(18) . ?
C16 H16 0.9500 . ?
C11 C12 1.3924(17) . ?
C9 C8 1.3879(19) . ?
C9 H9 0.9500 . ?
C3 H3 0.9500 . ?
C19 C20 1.3774(18) . ?
C19 H19 0.9500 . ?
C17 H17 0.9500 . ?
C22 C21 1.3832(19) . ?
C22 H22 0.9500 . ?
C20 C21 1.4035(19) . ?
C20 H20 0.9500 . ?
C15 C14 1.3909(19) . ?
C15 H15 0.9500 . ?
C12 C13 1.3906(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3875(19) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C21 H21 0.9500 . ?
C8 H8 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
C23 O1 B1 121.95(10) . . ?
C17 N3 C11 117.94(10) . . ?
C17 N3 B1 120.05(10) . . ?
C11 N3 B1 122.00(10) . . ?
C10 N2 C9 116.71(12) . . ?
C5 N1 C4 116.81(11) . . ?
N1 C4 C3 123.62(13) . . ?
N1 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
C8 C7 C6 118.86(12) . . ?
C8 C7 B1 131.28(11) . . ?
C6 C7 B1 109.50(11) . . ?
C19 C18 C23 120.56(11) . . ?
C19 C18 C17 121.05(11) . . ?
C23 C18 C17 118.09(11) . . ?
C5 C1 C2 116.81(12) . . ?
C5 C1 C6 132.53(12) . . ?
C2 C1 C6 110.65(11) . . ?
C3 C2 C1 118.55(11) . . ?
C3 C2 B1 132.23(11) . . ?
C1 C2 B1 109.22(11) . . ?
C10 C6 C7 115.78(12) . . ?
C10 C6 C1 133.58(12) . . ?
C7 C6 C1 110.58(11) . . ?
O1 C23 C22 119.93(11) . . ?
O1 C23 C18 121.10(11) . . ?
C22 C23 C18 118.88(11) . . ?
C11 C16 C15 119.65(11) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C11 C12 121.01(11) . . ?
C16 C11 N3 119.06(11) . . ?
C12 C11 N3 119.89(11) . . ?
N2 C9 C8 122.68(12) . . ?
N2 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C4 C3 C2 118.56(12) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C20 C19 C18 119.99(12) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
N3 C17 C18 122.46(11) . . ?
N3 C17 H17 118.8 . . ?
C18 C17 H17 118.8 . . ?
N2 C10 F1 113.38(11) . . ?
N2 C10 C6 126.66(12) . . ?
F1 C10 C6 119.94(12) . . ?
N1 C5 F2 114.16(11) . . ?
N1 C5 C1 125.64(12) . . ?
F2 C5 C1 120.19(12) . . ?
C21 C22 C23 119.42(12) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C19 C20 C21 119.12(12) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C16 C15 C14 119.92(12) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C13 C12 C11 118.67(12) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C14 C13 C12 120.83(12) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.92(12) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C22 C21 C20 121.95(12) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C7 C8 C9 119.31(12) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
O1 B1 N3 107.70(9) . . ?
O1 B1 C7 108.40(10) . . ?
N3 B1 C7 114.79(10) . . ?
O1 B1 C2 115.21(10) . . ?
N3 B1 C2 110.89(9) . . ?
C7 B1 C2 99.90(10) . . ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

_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_3e
_database_code_depnum_ccdc_archive 'CCDC 2243655'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Durka'
;Warsaw University of Technology, Faculty of Chemistry
Poland
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H17 B F2 N4 O'
_chemical_formula_weight         486.27

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'
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.4037(4)
_cell_length_b                   9.4998(5)
_cell_length_c                   13.2405(6)
_cell_angle_alpha                79.331(4)
_cell_angle_beta                 74.069(4)
_cell_angle_gamma                80.373(4)
_cell_volume                     1109.21(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8871
_cell_measurement_theta_min      2.2580
_cell_measurement_theta_max      28.4440

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             500
_exptl_absorpt_coefficient_mu    0.102
_exptl_crystal_size_max          0.603
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.072
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 1 -2 0.0990
-1 0 5 0.2563
5 -1 4 0.0985
5 -1 -1 0.1738
1 0 -5 0.3100
-5 1 -3 0.0960
5 1 5 0.1115
-5 -1 -3 0.0981
-1 -5 0 0.0459
1 5 0 0.0263
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.0066 0.9939 -2.0075 -0.1145 -0.3624 0.1349
-1.0018 -0.0005 5.0050 0.0278 0.0425 0.3072
5.0064 -0.9935 4.0098 0.1277 0.4045 -0.0311
5.0069 -0.9943 -0.9958 0.0949 0.2992 -0.2905
1.0018 0.0005 -5.0050 -0.0278 -0.0425 -0.3072
-5.0065 0.9937 -3.0087 -0.1211 -0.3835 0.0830
5.0058 1.0074 5.0059 -0.0186 0.4138 0.0202
-5.0060 -1.0071 -3.0037 0.0317 -0.3717 0.0836
-1.0002 -5.0033 0.0118 0.3769 -0.0334 0.0493
1.0002 5.0033 -0.0118 -0.3769 0.0334 -0.0493
_exptl_absorpt_correction_T_min  0.502
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.754
_oxdiff_exptl_absorpt_empirical_full_max 1.319
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_diffrn_ambient_temperature      100.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 8.0013
_diffrn_reflns_number            26344
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.198
_diffrn_reflns_theta_max         29.048
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5623
_reflns_number_gt                4522
_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_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'

_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)+(0.0413P)²+0.5666P] 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         5623
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.67693(11) 0.40075(11) 0.48210(8) 0.0319(3) Uani 1 1 d . . . . .
F2 F 0.58624(12) 0.57574(11) 0.62472(9) 0.0353(3) Uani 1 1 d . . . . .
O1 O 0.40243(13) 0.02249(12) 0.87905(9) 0.0233(3) Uani 1 1 d . . . . .
N3 N 0.21871(14) 0.10802(13) 0.77131(10) 0.0160(3) Uani 1 1 d . . . . .
N4 N 0.04051(14) -0.01837(13) 0.77121(10) 0.0165(3) Uani 1 1 d . . . . .
C17 C 0.17897(17) -0.09253(16) 0.91537(12) 0.0167(3) Uani 1 1 d . . . . .
C5 C 0.49916(16) 0.12166(16) 0.67969(12) 0.0176(3) Uani 1 1 d . . . . .
C23 C 0.14576(16) -0.00561(16) 0.82049(12) 0.0159(3) Uani 1 1 d . . . . .
C6 C 0.47555(17) 0.36362(17) 0.71112(12) 0.0186(3) Uani 1 1 d . . . . .
C18 C 0.08334(17) -0.18584(17) 0.98686(12) 0.0193(3) Uani 1 1 d . . . . .
H18 H -0.0071 -0.1975 0.9723 0.023 Uiso 1 1 calc R U . . .
N1 N 0.69422(15) 0.16351(17) 0.47852(11) 0.0264(3) Uani 1 1 d . . . . .
N2 N 0.43444(16) 0.58326(15) 0.78670(13) 0.0279(3) Uani 1 1 d . . . . .
C12 C 0.15592(16) 0.17459(16) 0.68702(12) 0.0161(3) Uani 1 1 d . . . . .
C1 C 0.54399(16) 0.25886(17) 0.63575(12) 0.0182(3) Uani 1 1 d . . . . .
C10 C 0.37761(17) 0.29807(17) 0.80250(12) 0.0187(3) Uani 1 1 d . . . . .
C24 C -0.03633(17) -0.14207(16) 0.78119(12) 0.0178(3) Uani 1 1 d . . . . .
C29 C 0.04807(18) -0.27002(17) 0.75482(13) 0.0215(3) Uani 1 1 d . . . . .
H29 H 0.1538 -0.2783 0.7357 0.026 Uiso 1 1 calc R U . . .
C19 C 0.11949(19) -0.26048(17) 1.07776(13) 0.0232(3) Uani 1 1 d . . . . .
H19 H 0.0537 -0.3223 1.1261 0.028 Uiso 1 1 calc R U . . .
C13 C 0.18972(17) 0.29461(16) 0.61031(12) 0.0185(3) Uani 1 1 d . . . . .
H13 H 0.2638 0.3511 0.6110 0.022 Uiso 1 1 calc R U . . .
C9 C 0.31021(19) 0.37797(18) 0.88429(13) 0.0244(4) Uani 1 1 d . . . . .
H9 H 0.2428 0.3378 0.9464 0.029 Uiso 1 1 calc R U . . .
C16 C -0.03411(17) 0.12530(17) 0.60899(13) 0.0203(3) Uani 1 1 d . . . . .
H16 H -0.1084 0.0689 0.6087 0.024 Uiso 1 1 calc R U . . .
C2 C 0.63710(18) 0.27065(19) 0.53366(13) 0.0231(3) Uani 1 1 d . . . . .
C4 C 0.55845(18) 0.00638(18) 0.62355(13) 0.0220(3) Uani 1 1 d . . . . .
H4 H 0.5321 -0.0878 0.6521 0.026 Uiso 1 1 calc R U . . .
C21 C 0.34905(19) -0.15259(17) 1.02998(13) 0.0230(3) Uani 1 1 d . . . . .
H21 H 0.4407 -0.1443 1.0443 0.028 Uiso 1 1 calc R U . . .
C3 C 0.65721(18) 0.0325(2) 0.52469(14) 0.0264(4) Uani 1 1 d . . . . .
H3 H 0.7010 -0.0471 0.4878 0.032 Uiso 1 1 calc R U . . .
C14 C 0.11076(17) 0.32752(17) 0.53354(13) 0.0202(3) Uani 1 1 d . . . . .
H14 H 0.1305 0.4090 0.4804 0.024 Uiso 1 1 calc R U . . .
C11 C 0.04467(17) 0.09440(16) 0.68630(12) 0.0166(3) Uani 1 1 d . . . . .
C25 C -0.19134(18) -0.12660(18) 0.80850(13) 0.0231(3) Uani 1 1 d . . . . .
H25 H -0.2471 -0.0375 0.8261 0.028 Uiso 1 1 calc R U . . .
C20 C 0.2537(2) -0.24477(18) 1.09851(13) 0.0241(4) Uani 1 1 d . . . . .
H20 H 0.2797 -0.2980 1.1604 0.029 Uiso 1 1 calc R U . . .
C28 C -0.0257(2) -0.38637(18) 0.75694(14) 0.0269(4) Uani 1 1 d . . . . .
H28 H 0.0301 -0.4756 0.7398 0.032 Uiso 1 1 calc R U . . .
C7 C 0.49492(18) 0.50575(18) 0.70999(14) 0.0239(4) Uani 1 1 d . . . . .
C15 C 0.00157(18) 0.24367(18) 0.53176(13) 0.0218(3) Uani 1 1 d . . . . .
H15 H -0.0488 0.2685 0.4766 0.026 Uiso 1 1 calc R U . . .
B1 B 0.3716(2) 0.13147(19) 0.79023(14) 0.0183(3) Uani 1 1 d . . . . .
C22 C 0.31056(17) -0.07128(16) 0.93924(12) 0.0185(3) Uani 1 1 d . . . . .
C26 C -0.2632(2) -0.24347(19) 0.80964(15) 0.0286(4) Uani 1 1 d . . . . .
H26 H -0.3689 -0.2349 0.8280 0.034 Uiso 1 1 calc R U . . .
C27 C -0.1802(2) -0.37266(19) 0.78393(15) 0.0299(4) Uani 1 1 d . . . . .
H27 H -0.2296 -0.4525 0.7848 0.036 Uiso 1 1 calc R U . . .
C8 C 0.3431(2) 0.5185(2) 0.87384(15) 0.0308(4) Uani 1 1 d . . . . .
H8 H 0.2987 0.5715 0.9312 0.037 Uiso 1 1 calc R U . . .


_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 C2 1.3549(19) . ?
F2 C7 1.3546(19) . ?
O1 C22 1.3385(18) . ?
O1 B1 1.475(2) . ?
N3 C23 1.3424(19) . ?
N3 C12 1.4035(19) . ?
N3 B1 1.583(2) . ?
N4 C23 1.3579(19) . ?
N4 C11 1.3989(19) . ?
N4 C24 1.4473(19) . ?
C17 C18 1.407(2) . ?
C17 C22 1.412(2) . ?
C17 C23 1.450(2) . ?
C5 C4 1.390(2) . ?
C5 C1 1.408(2) . ?
C5 B1 1.624(2) . ?
C6 C7 1.389(2) . ?
C6 C10 1.415(2) . ?
C6 C1 1.484(2) . ?
C18 C19 1.377(2) . ?
C18 H18 0.9500 . ?
N1 C2 1.317(2) . ?
N1 C3 1.338(2) . ?
N2 C7 1.310(2) . ?
N2 C8 1.348(2) . ?
C12 C13 1.396(2) . ?
C12 C11 1.396(2) . ?
C1 C2 1.390(2) . ?
C10 C9 1.385(2) . ?
C10 B1 1.632(2) . ?
C24 C29 1.383(2) . ?
C24 C25 1.391(2) . ?
C29 C28 1.392(2) . ?
C29 H29 0.9500 . ?
C19 C20 1.400(2) . ?
C19 H19 0.9500 . ?
C13 C14 1.379(2) . ?
C13 H13 0.9500 . ?
C9 C8 1.394(2) . ?
C9 H9 0.9500 . ?
C16 C11 1.384(2) . ?
C16 C15 1.391(2) . ?
C16 H16 0.9500 . ?
C4 C3 1.388(2) . ?
C4 H4 0.9500 . ?
C21 C20 1.384(2) . ?
C21 C22 1.405(2) . ?
C21 H21 0.9500 . ?
C3 H3 0.9500 . ?
C14 C15 1.408(2) . ?
C14 H14 0.9500 . ?
C25 C26 1.389(2) . ?
C25 H25 0.9500 . ?
C20 H20 0.9500 . ?
C28 C27 1.388(3) . ?
C28 H28 0.9500 . ?
C15 H15 0.9500 . ?
C26 C27 1.385(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C8 H8 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
C22 O1 B1 125.76(12) . . ?
C23 N3 C12 107.50(12) . . ?
C23 N3 B1 123.16(13) . . ?
C12 N3 B1 127.60(12) . . ?
C23 N4 C11 107.81(12) . . ?
C23 N4 C24 128.12(13) . . ?
C11 N4 C24 122.16(12) . . ?
C18 C17 C22 119.54(14) . . ?
C18 C17 C23 123.92(14) . . ?
C22 C17 C23 116.35(13) . . ?
C4 C5 C1 119.10(14) . . ?
C4 C5 B1 130.65(14) . . ?
C1 C5 B1 110.11(13) . . ?
N3 C23 N4 110.53(13) . . ?
N3 C23 C17 120.99(13) . . ?
N4 C23 C17 128.44(13) . . ?
C7 C6 C10 116.77(15) . . ?
C7 C6 C1 132.62(15) . . ?
C10 C6 C1 110.53(13) . . ?
C19 C18 C17 120.67(15) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C2 N1 C3 116.77(14) . . ?
C7 N2 C8 116.27(15) . . ?
C13 C12 C11 120.86(14) . . ?
C13 C12 N3 131.61(14) . . ?
C11 C12 N3 107.50(13) . . ?
C2 C1 C5 116.24(14) . . ?
C2 C1 C6 133.38(15) . . ?
C5 C1 C6 110.36(13) . . ?
C9 C10 C6 118.39(15) . . ?
C9 C10 B1 131.91(15) . . ?
C6 C10 B1 109.66(13) . . ?
C29 C24 C25 121.97(15) . . ?
C29 C24 N4 118.14(14) . . ?
C25 C24 N4 119.69(14) . . ?
C24 C29 C28 118.39(15) . . ?
C24 C29 H29 120.8 . . ?
C28 C29 H29 120.8 . . ?
C18 C19 C20 119.62(15) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C14 C13 C12 116.97(14) . . ?
C14 C13 H13 121.5 . . ?
C12 C13 H13 121.5 . . ?
C10 C9 C8 118.78(16) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C11 C16 C15 116.22(14) . . ?
C11 C16 H16 121.9 . . ?
C15 C16 H16 121.9 . . ?
N1 C2 F1 113.98(14) . . ?
N1 C2 C1 125.71(15) . . ?
F1 C2 C1 120.31(15) . . ?
C3 C4 C5 118.25(16) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C20 C21 C22 120.09(15) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
N1 C3 C4 123.66(16) . . ?
N1 C3 H3 118.2 . . ?
C4 C3 H3 118.2 . . ?
C13 C14 C15 121.77(14) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C16 C11 C12 122.70(14) . . ?
C16 C11 N4 130.57(14) . . ?
C12 C11 N4 106.64(13) . . ?
C26 C25 C24 118.90(16) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C21 C20 C19 120.84(15) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C27 C28 C29 120.35(16) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
N2 C7 F2 113.79(14) . . ?
N2 C7 C6 126.17(16) . . ?
F2 C7 C6 120.01(15) . . ?
C16 C15 C14 121.45(14) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
O1 B1 N3 108.14(12) . . ?
O1 B1 C5 113.60(13) . . ?
N3 B1 C5 108.11(12) . . ?
O1 B1 C10 115.06(13) . . ?
N3 B1 C10 112.88(13) . . ?
C5 B1 C10 98.72(12) . . ?
O1 C22 C21 117.66(14) . . ?
O1 C22 C17 123.28(14) . . ?
C21 C22 C17 119.05(14) . . ?
C27 C26 C25 119.85(16) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C28 120.54(16) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
N2 C8 C9 123.57(16) . . ?
N2 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4

_exptl_crystal_preparation       Luminescent
