# Supplementary Information (SI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_psi140227F1
_database_code_depnum_ccdc_archive 'CCDC 2189206'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2022-07-10 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 B2 F4 N3 O3'
_chemical_formula_sum            'C15 H17 B2 F4 N3 O3'
_chemical_formula_weight         384.93

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'
O O 0.0106 0.0060 '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'
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                   8.3810(3)
_cell_length_b                   18.3330(8)
_cell_length_c                   12.3330(11)
_cell_angle_alpha                90
_cell_angle_beta                 120.667(5)
_cell_angle_gamma                90
_cell_volume                     1629.93(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    12342
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.293
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6685
_exptl_absorpt_correction_T_max  0.7654
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.873
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_reflns_number            12342
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.937
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3589
_reflns_number_gt                3029
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0379P)²+0.7169P] 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         3589
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 1.04668(11) 0.06339(5) 0.26439(8) 0.0288(2) Uani 1 1 d . . . . .
C1 C 0.78725(17) 0.13742(7) -0.00878(12) 0.0165(3) Uani 1 1 d . . . . .
N1 N 0.71235(14) 0.05828(6) 0.14820(10) 0.0170(2) Uani 1 1 d . . . . .
O1 O 0.89944(12) 0.08484(5) 0.04913(9) 0.0204(2) Uani 1 1 d . . . . .
B1 B 0.8994(2) 0.04163(8) 0.15138(15) 0.0200(3) Uani 1 1 d . . . . .
F2 F 0.90827(12) -0.03037(4) 0.12831(9) 0.0291(2) Uani 1 1 d . . . . .
C2 C 0.63537(17) 0.15167(7) 0.00836(12) 0.0166(3) Uani 1 1 d . . . . .
N2 N 0.60052(14) 0.11024(6) 0.08351(10) 0.0166(2) Uani 1 1 d . . . . .
O2 O 0.81731(12) 0.17481(5) -0.08392(9) 0.0201(2) Uani 1 1 d . . . . .
B2 B 0.7090(2) 0.24173(8) -0.15196(14) 0.0191(3) Uani 1 1 d . . . . .
F3 F 0.82226(11) 0.30099(5) -0.10046(9) 0.0306(2) Uani 1 1 d . . . . .
C3 C 0.50620(17) 0.20910(7) -0.06163(12) 0.0162(2) Uani 1 1 d . . . . .
N3 N 0.53708(14) 0.24938(6) -0.13570(10) 0.0163(2) Uani 1 1 d . . . . .
O3 O 0.50354(13) -0.09423(5) 0.44620(9) 0.0247(2) Uani 1 1 d . . . . .
F4 F 0.65220(12) 0.23340(5) -0.27643(8) 0.0285(2) Uani 1 1 d . . . . .
C4 C 0.33753(18) 0.21904(7) -0.05153(12) 0.0189(3) Uani 1 1 d . . . . .
H4A H 0.327504 0.269897 -0.034122 0.023 Uiso 1 1 calc R U . . .
H4AB H 0.350430 0.190329 0.018572 0.023 Uiso 1 1 calc R U . . .
C5 C 0.15967(18) 0.19602(8) -0.17248(13) 0.0212(3) Uani 1 1 d . . . . .
H5A H 0.184391 0.151832 -0.204682 0.025 Uiso 1 1 calc R U . . .
H5AB H 0.064952 0.184825 -0.151985 0.025 Uiso 1 1 calc R U . . .
C6 C 0.08551(18) 0.25372(8) -0.27505(13) 0.0234(3) Uani 1 1 d . . . . .
H6A H 0.054862 0.297013 -0.244165 0.028 Uiso 1 1 calc R U . . .
H6AB H -0.028189 0.235831 -0.347053 0.028 Uiso 1 1 calc R U . . .
C9 C 0.65441(18) 0.01611(7) 0.21995(12) 0.0177(3) Uani 1 1 d . . . . .
C8 C 0.40289(18) 0.30671(7) -0.21493(13) 0.0192(3) Uani 1 1 d . . . . .
H8A H 0.457460 0.336214 -0.252980 0.023 Uiso 1 1 calc R U . . .
H8AB H 0.378646 0.338286 -0.161840 0.023 Uiso 1 1 calc R U . . .
C7 C 0.22006(18) 0.27493(8) -0.31863(13) 0.0215(3) Uani 1 1 d . . . . .
H7A H 0.246371 0.232072 -0.353005 0.026 Uiso 1 1 calc R U . . .
H7AB H 0.160279 0.310458 -0.385993 0.026 Uiso 1 1 calc R U . . .
C14 C 0.46831(18) 0.01308(7) 0.18358(12) 0.0191(3) Uani 1 1 d . . . . .
H14 H 0.380613 0.036336 0.110014 0.023 Uiso 1 1 calc R U . . .
C13 C 0.41204(18) -0.02430(7) 0.25595(13) 0.0202(3) Uani 1 1 d . . . . .
H13 H 0.287093 -0.026070 0.231222 0.024 Uiso 1 1 calc R U . . .
C12 C 0.54348(18) -0.05920(7) 0.36590(12) 0.0190(3) Uani 1 1 d . . . . .
C11 C 0.72967(19) -0.05865(7) 0.39962(13) 0.0218(3) Uani 1 1 d . . . . .
H11 H 0.816836 -0.083725 0.471074 0.026 Uiso 1 1 calc R U . . .
C10 C 0.78525(18) -0.02102(7) 0.32736(13) 0.0207(3) Uani 1 1 d . . . . .
H10 H 0.909601 -0.020497 0.350411 0.025 Uiso 1 1 calc R U . . .
C15 C 0.3144(2) -0.09176(8) 0.41649(14) 0.0265(3) Uani 1 1 d . . . . .
H15A H 0.304084 -0.115441 0.482083 0.040 Uiso 1 1 calc R U . . .
H15B H 0.236933 -0.116321 0.337915 0.040 Uiso 1 1 calc R U . . .
H15C H 0.275569 -0.041867 0.409602 0.040 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 B1 1.3677(18) . ?
C1 O2 1.2767(15) . ?
C1 O1 1.2800(15) . ?
C1 C2 1.4170(17) . ?
N1 N2 1.2882(15) . ?
N1 C9 1.4335(16) . ?
N1 B1 1.5778(17) . ?
O1 B1 1.4895(17) . ?
B1 F2 1.3603(18) . ?
C2 N2 1.3407(16) . ?
C2 C3 1.4397(17) . ?
O2 B2 1.5021(17) . ?
B2 F4 1.3641(18) . ?
B2 F3 1.3672(17) . ?
B2 N3 1.5595(17) . ?
C3 N3 1.2992(16) . ?
C3 C4 1.4922(17) . ?
N3 C8 1.4843(16) . ?
O3 C12 1.3577(15) . ?
O3 C15 1.4341(17) . ?
C4 C5 1.5352(19) . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C5 C6 1.5176(19) . ?
C5 H5A 0.9700 . ?
C5 H5AB 0.9700 . ?
C6 C7 1.5265(18) . ?
C6 H6A 0.9700 . ?
C6 H6AB 0.9700 . ?
C9 C14 1.3868(18) . ?
C9 C10 1.3924(18) . ?
C8 C7 1.5244(19) . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C14 C13 1.3849(18) . ?
C14 H14 0.9300 . ?
C13 C12 1.3921(19) . ?
C13 H13 0.9300 . ?
C12 C11 1.3951(19) . ?
C11 C10 1.3822(19) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
O2 C1 O1 116.65(11) . . ?
O2 C1 C2 122.29(11) . . ?
O1 C1 C2 121.04(11) . . ?
N2 N1 C9 114.36(10) . . ?
N2 N1 B1 123.94(10) . . ?
C9 N1 B1 121.69(10) . . ?
C1 O1 B1 123.76(10) . . ?
F2 B1 F1 112.27(12) . . ?
F2 B1 O1 108.38(12) . . ?
F1 B1 O1 108.53(11) . . ?
F2 B1 N1 110.02(11) . . ?
F1 B1 N1 109.74(11) . . ?
O1 B1 N1 107.78(10) . . ?
N2 C2 C1 121.86(11) . . ?
N2 C2 C3 117.80(11) . . ?
C1 C2 C3 120.22(11) . . ?
N1 N2 C2 120.05(11) . . ?
C1 O2 B2 123.88(10) . . ?
F4 B2 F3 111.90(12) . . ?
F4 B2 O2 107.58(11) . . ?
F3 B2 O2 108.13(11) . . ?
F4 B2 N3 109.85(11) . . ?
F3 B2 N3 109.68(11) . . ?
O2 B2 N3 109.64(10) . . ?
N3 C3 C2 118.60(11) . . ?
N3 C3 C4 121.75(11) . . ?
C2 C3 C4 119.60(11) . . ?
C3 N3 C8 120.63(10) . . ?
C3 N3 B2 124.61(11) . . ?
C8 N3 B2 114.75(10) . . ?
C12 O3 C15 116.77(10) . . ?
C3 C4 C5 112.15(11) . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4AB 109.2 . . ?
C5 C4 H4AB 109.2 . . ?
H4A C4 H4AB 107.9 . . ?
C6 C5 C4 113.59(11) . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5AB 108.8 . . ?
C4 C5 H5AB 108.8 . . ?
H5A C5 H5AB 107.7 . . ?
C5 C6 C7 114.14(11) . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6AB 108.7 . . ?
C7 C6 H6AB 108.7 . . ?
H6A C6 H6AB 107.6 . . ?
C14 C9 C10 119.88(12) . . ?
C14 C9 N1 120.07(11) . . ?
C10 C9 N1 120.04(11) . . ?
N3 C8 C7 112.43(11) . . ?
N3 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
N3 C8 H8AB 109.1 . . ?
C7 C8 H8AB 109.1 . . ?
H8A C8 H8AB 107.8 . . ?
C8 C7 C6 114.14(11) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7AB 108.7 . . ?
C6 C7 H7AB 108.7 . . ?
H7A C7 H7AB 107.6 . . ?
C13 C14 C9 120.52(12) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C14 C13 C12 119.66(12) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
O3 C12 C13 124.12(12) . . ?
O3 C12 C11 116.13(12) . . ?
C13 C12 C11 119.74(12) . . ?
C10 C11 C12 120.33(12) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C10 C9 119.77(12) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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_psi140227F2
_database_code_depnum_ccdc_archive 'CCDC 2189207'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2022-07-10 deposited with the CCDC.	2024-08-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H22 B F2 N3 O3'
_chemical_formula_sum            'C17 H22 B F2 N3 O3'
_chemical_formula_weight         365.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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'
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                   10.8390(7)
_cell_length_b                   10.5720(10)
_cell_length_c                   15.3710(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.905(5)
_cell_angle_gamma                90
_cell_volume                     1740.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    13196
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.438
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6387
_exptl_absorpt_correction_T_max  0.7654
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.8344
;
_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_reflns_number            13196
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.888
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3927
_reflns_number_gt                2865
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0362P)²+0.6861P] 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         3927
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0858
_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
F1 F 0.29016(9) -0.16601(9) 0.60279(6) 0.0317(2) Uani 1 1 d . . . . .
C1 C 0.16829(14) -0.01866(15) 0.79379(9) 0.0251(3) Uani 1 1 d . . . . .
O1 O -0.00218(11) -0.03936(12) 0.87434(8) 0.0410(3) Uani 1 1 d . . . . .
N1 N 0.27069(11) 0.03170(12) 0.67920(7) 0.0236(3) Uani 1 1 d . . . . .
B1 B 0.33536(16) -0.09807(18) 0.67830(11) 0.0261(4) Uani 1 1 d . . . . .
N2 N 0.19285(11) 0.06247(12) 0.73320(8) 0.0243(3) Uani 1 1 d . . . . .
C2 C 0.07412(15) 0.02752(16) 0.84775(10) 0.0275(3) Uani 1 1 d . . . . .
O2 O 0.08404(10) 0.15128(10) 0.86292(7) 0.0286(3) Uani 1 1 d . . . . .
F2 F 0.46350(8) -0.08286(10) 0.68272(6) 0.0364(2) Uani 1 1 d . . . . .
N3 N 0.30961(12) -0.17150(13) 0.76022(8) 0.0268(3) Uani 1 1 d . . . . .
O3 O 0.37240(11) 0.42604(11) 0.45959(7) 0.0321(3) Uani 1 1 d . . . . .
C3 C 0.22973(14) -0.13712(15) 0.81152(9) 0.0269(3) Uani 1 1 d . . . . .
C7 C 0.29932(18) -0.40733(17) 0.75607(11) 0.0381(4) Uani 1 1 d . . . . .
H7A H 0.351752 -0.477829 0.744568 0.046 Uiso 1 1 calc R U . . .
H7AB H 0.240612 -0.391901 0.702789 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2266(2) -0.44495(19) 0.82879(13) 0.0503(5) Uani 1 1 d . . . . .
H6A H 0.285548 -0.468721 0.880286 0.060 Uiso 1 1 calc R U . . .
H6AB H 0.176913 -0.519067 0.809805 0.060 Uiso 1 1 calc R U . . .
C5 C 0.1407(2) -0.34308(18) 0.85535(13) 0.0468(5) Uani 1 1 d . . . . .
H5A H 0.098801 -0.375756 0.902033 0.056 Uiso 1 1 calc R U . . .
H5AB H 0.077140 -0.324167 0.805343 0.056 Uiso 1 1 calc R U . . .
C4 C 0.20844(18) -0.21992(17) 0.88706(11) 0.0373(4) Uani 1 1 d . . . . .
H4A H 0.159146 -0.174142 0.924239 0.045 Uiso 1 1 calc R U . . .
H4AB H 0.288217 -0.240288 0.922175 0.045 Uiso 1 1 calc R U . . .
C8 C 0.38072(16) -0.29146(17) 0.77571(11) 0.0360(4) Uani 1 1 d . . . . .
H8A H 0.420697 -0.294448 0.836668 0.043 Uiso 1 1 calc R U . . .
H8AB H 0.445826 -0.292844 0.738952 0.043 Uiso 1 1 calc R U . . .
C10 C 0.01950(16) 0.34289(17) 0.92202(12) 0.0363(4) Uani 1 1 d . . . . .
H10A H -0.036706 0.381150 0.956811 0.054 Uiso 1 1 calc R U . . .
H10B H 0.004247 0.376835 0.863409 0.054 Uiso 1 1 calc R U . . .
H10C H 0.104072 0.360518 0.948058 0.054 Uiso 1 1 calc R U . . .
C9 C -0.00087(15) 0.20332(16) 0.91857(11) 0.0313(4) Uani 1 1 d . . . . .
H9A H 0.016628 0.167403 0.977256 0.038 Uiso 1 1 calc R U . . .
H9AB H -0.086734 0.184217 0.893981 0.038 Uiso 1 1 calc R U . . .
C12 C 0.36124(14) 0.10646(15) 0.55253(9) 0.0259(3) Uani 1 1 d . . . . .
H12 H 0.387971 0.024403 0.544098 0.031 Uiso 1 1 calc R U . . .
C11 C 0.29386(13) 0.13143(15) 0.62054(9) 0.0237(3) Uani 1 1 d . . . . .
C15 C 0.27845(15) 0.34877(16) 0.57569(10) 0.0308(4) Uani 1 1 d . . . . .
H15 H 0.249203 0.430237 0.582780 0.037 Uiso 1 1 calc R U . . .
C14 C 0.34887(14) 0.32409(15) 0.50908(9) 0.0264(3) Uani 1 1 d . . . . .
C16 C 0.25178(15) 0.25394(16) 0.63100(10) 0.0297(4) Uani 1 1 d . . . . .
H16 H 0.205411 0.271749 0.675611 0.036 Uiso 1 1 calc R U . . .
C17 C 0.44930(16) 0.40332(18) 0.39375(11) 0.0355(4) Uani 1 1 d . . . . .
H17A H 0.463951 0.481561 0.365343 0.053 Uiso 1 1 calc R U . . .
H17B H 0.408077 0.345036 0.350922 0.053 Uiso 1 1 calc R U . . .
H17C H 0.527579 0.368077 0.420709 0.053 Uiso 1 1 calc R U . . .
C13 C 0.38908(14) 0.20208(15) 0.49721(9) 0.0262(3) Uani 1 1 d . . . . .
H13 H 0.434708 0.184314 0.452175 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
F1 B1 1.3882(19) . ?
C1 N2 1.3231(19) . ?
C1 C3 1.425(2) . ?
C1 C2 1.493(2) . ?
O1 C2 1.2065(19) . ?
N1 N2 1.3128(16) . ?
N1 C11 1.4345(19) . ?
N1 B1 1.542(2) . ?
B1 F2 1.3894(19) . ?
B1 N3 1.541(2) . ?
C2 O2 1.330(2) . ?
O2 C9 1.4577(17) . ?
N3 C3 1.3096(19) . ?
N3 C8 1.484(2) . ?
O3 C14 1.3658(18) . ?
O3 C17 1.4275(18) . ?
C3 C4 1.500(2) . ?
C7 C8 1.512(3) . ?
C7 C6 1.517(3) . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C6 C5 1.521(3) . ?
C6 H6A 0.9700 . ?
C6 H6AB 0.9700 . ?
C5 C4 1.537(3) . ?
C5 H5A 0.9700 . ?
C5 H5AB 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C10 C9 1.492(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9AB 0.9700 . ?
C12 C13 1.384(2) . ?
C12 C11 1.390(2) . ?
C12 H12 0.9300 . ?
C11 C16 1.391(2) . ?
C15 C16 1.374(2) . ?
C15 C14 1.393(2) . ?
C15 H15 0.9300 . ?
C14 C13 1.383(2) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C13 H13 0.9300 . ?

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
N2 C1 C3 124.44(13) . . ?
N2 C1 C2 114.10(14) . . ?
C3 C1 C2 121.37(13) . . ?
N2 N1 C11 114.05(12) . . ?
N2 N1 B1 124.31(12) . . ?
C11 N1 B1 121.62(11) . . ?
F1 B1 F2 108.75(13) . . ?
F1 B1 N3 109.72(13) . . ?
F2 B1 N3 108.94(13) . . ?
F1 B1 N1 111.46(13) . . ?
F2 B1 N1 110.43(13) . . ?
N3 B1 N1 107.51(12) . . ?
N1 N2 C1 120.23(13) . . ?
O1 C2 O2 123.92(14) . . ?
O1 C2 C1 124.04(15) . . ?
O2 C2 C1 112.04(13) . . ?
C2 O2 C9 115.65(12) . . ?
C3 N3 C8 121.06(13) . . ?
C3 N3 B1 124.92(13) . . ?
C8 N3 B1 113.97(12) . . ?
C14 O3 C17 116.23(12) . . ?
N3 C3 C1 117.50(14) . . ?
N3 C3 C4 119.95(15) . . ?
C1 C3 C4 122.52(14) . . ?
C8 C7 C6 114.75(15) . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7AB 108.6 . . ?
C6 C7 H7AB 108.6 . . ?
H7A C7 H7AB 107.6 . . ?
C7 C6 C5 114.95(16) . . ?
C7 C6 H6A 108.5 . . ?
C5 C6 H6A 108.5 . . ?
C7 C6 H6AB 108.5 . . ?
C5 C6 H6AB 108.5 . . ?
H6A C6 H6AB 107.5 . . ?
C6 C5 C4 113.73(17) . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5AB 108.8 . . ?
C4 C5 H5AB 108.8 . . ?
H5A C5 H5AB 107.7 . . ?
C3 C4 C5 111.85(14) . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4AB 109.2 . . ?
C5 C4 H4AB 109.2 . . ?
H4A C4 H4AB 107.9 . . ?
N3 C8 C7 112.81(14) . . ?
N3 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
N3 C8 H8AB 109.0 . . ?
C7 C8 H8AB 109.0 . . ?
H8A C8 H8AB 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C9 C10 106.90(13) . . ?
O2 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
O2 C9 H9AB 110.3 . . ?
C10 C9 H9AB 110.3 . . ?
H9A C9 H9AB 108.6 . . ?
C13 C12 C11 120.88(15) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C11 C16 118.93(14) . . ?
C12 C11 N1 119.78(14) . . ?
C16 C11 N1 121.28(13) . . ?
C16 C15 C14 120.65(15) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
O3 C14 C13 124.95(13) . . ?
O3 C14 C15 115.61(14) . . ?
C13 C14 C15 119.44(14) . . ?
C15 C16 C11 120.25(14) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C13 C12 119.81(13) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.047



