# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2025

####################################################################### 
# 
# 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_ry8221222_21_wuse_0m
_database_code_depnum_ccdc_archive 'CCDC 2365183'
loop_
_audit_author_name
_audit_author_address
'Tingting zhao'
;Changchun University of Science and Technology
China
;
_audit_update_record             
;
2024-06-24 deposited with the CCDC.	2025-01-17 downloaded from the CCDC.
;
_audit_creation_date             2022-12-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H36 B2 F4 N4'
_chemical_formula_sum            'C34 H36 B2 F4 N4'
_chemical_formula_weight         598.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0070 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2488(9)
_cell_length_b                   8.9759(12)
_cell_length_c                   14.662(2)
_cell_angle_alpha                72.625(5)
_cell_angle_beta                 79.192(5)
_cell_angle_gamma                71.413(4)
_cell_volume                     740.04(18)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3546
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.419
_cell_measurement_theta_min      2.761
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1045 before and 0.0647 after correction.
The Ratio of minimum to maximum transmission is 0.7101.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             314
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10649
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.799
_diffrn_reflns_theta_min         2.762
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2503
_reflns_number_total             3356
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0695
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1058P)²+0.2703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1878
_refine_ls_wR_factor_ref         0.2013
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C13(H13)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.2143(3) 0.91055(15) 0.51798(12) 0.0537(5) Uani 1 1 d . . . . .
F2 F -0.4103(2) 0.7689(2) 0.63945(11) 0.0598(5) Uani 1 1 d . . . . .
N1 N 0.2595(3) 0.3347(2) 0.49926(12) 0.0274(4) Uani 1 1 d . . . . .
N2 N -0.0069(3) 0.6613(2) 0.61799(12) 0.0300(4) Uani 1 1 d . . . . .
C1 C 0.9879(4) 0.1852(3) 0.86951(17) 0.0424(5) Uani 1 1 d . . . . .
H1 H 0.856892 0.249417 0.898804 0.051 Uiso 1 1 calc R U . . .
C2 C 1.1809(4) 0.1111(3) 0.91769(18) 0.0515(7) Uani 1 1 d . . . . .
H2 H 1.181325 0.124612 0.979489 0.062 Uiso 1 1 calc R U . . .
C3 C 1.3727(4) 0.0176(3) 0.87555(18) 0.0478(6) Uani 1 1 d . . . . .
H3 H 1.505452 -0.032799 0.908191 0.057 Uiso 1 1 calc R U . . .
C4 C 1.3707(4) -0.0022(3) 0.78616(16) 0.0381(5) Uani 1 1 d . . . . .
H4 H 1.502387 -0.066951 0.757545 0.046 Uiso 1 1 calc R U . . .
C5 C 1.1779(3) 0.0716(3) 0.73734(15) 0.0328(5) Uani 1 1 d . . . . .
H5 H 1.178537 0.057272 0.675652 0.039 Uiso 1 1 calc R U . . .
C6 C 0.9827(3) 0.1670(2) 0.77902(15) 0.0318(5) Uani 1 1 d . . . . .
C7 C 0.7733(3) 0.2495(3) 0.73120(15) 0.0336(5) Uani 1 1 d . . . . .
H7 H 0.657076 0.321187 0.762303 0.040 Uiso 1 1 calc R U . . .
C8 C 0.7278(3) 0.2355(2) 0.64971(15) 0.0302(4) Uani 1 1 d . . . . .
H8 H 0.842187 0.166249 0.616471 0.036 Uiso 1 1 calc R U . . .
C9 C 0.5113(3) 0.3206(2) 0.60765(14) 0.0281(4) Uani 1 1 d . . . . .
C10 C 0.4581(3) 0.2638(2) 0.53857(15) 0.0296(4) Uani 1 1 d . . . . .
H10 H 0.563414 0.173492 0.518771 0.036 Uiso 1 1 calc R U . . .
C11 C 0.1029(3) 0.4652(2) 0.52375(13) 0.0265(4) Uani 1 1 d . . . . .
C12 C 0.1466(3) 0.5303(2) 0.59385(14) 0.0267(4) Uani 1 1 d . . . . .
C13 C 0.3545(3) 0.4531(2) 0.63460(14) 0.0297(4) Uani 1 1 d . . . . .
H13 H 0.387804 0.493030 0.681857 0.036 Uiso 1 1 calc R U . . .
C14 C 0.0336(3) 0.7217(2) 0.69455(15) 0.0309(4) Uani 1 1 d . . . . .
H14A H -0.058840 0.836140 0.687468 0.037 Uiso 1 1 calc R U . . .
H14B H 0.195353 0.719338 0.687114 0.037 Uiso 1 1 calc R U . . .
C15 C -0.0251(4) 0.6213(3) 0.79474(16) 0.0391(5) Uani 1 1 d . . . . .
H15A H 0.051275 0.504880 0.798673 0.047 Uiso 1 1 calc R U . . .
H15B H -0.190861 0.635760 0.805159 0.047 Uiso 1 1 calc R U . . .
C16 C 0.0451(4) 0.6679(3) 0.87455(17) 0.0466(6) Uani 1 1 d . . . . .
H16A H 0.007813 0.787882 0.859799 0.056 Uiso 1 1 calc R U . . .
H16B H -0.043404 0.630283 0.935901 0.056 Uiso 1 1 calc R U . . .
C17 C 0.2975(5) 0.5949(4) 0.8865(2) 0.0599(7) Uani 1 1 d . . . . .
H17A H 0.386020 0.633345 0.826267 0.090 Uiso 1 1 calc R U . . .
H17B H 0.334686 0.476043 0.902691 0.090 Uiso 1 1 calc R U . . .
H17C H 0.334089 0.628480 0.938065 0.090 Uiso 1 1 calc R U . . .
B1 B -0.2215(4) 0.7547(3) 0.57214(18) 0.0333(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.398(3) . ?
F2 B1 1.387(3) . ?
N1 C10 1.350(2) . ?
N1 C11 1.360(2) . ?
N1 B1 1.585(3) 2_566 ?
N2 C12 1.353(2) . ?
N2 C14 1.475(2) . ?
N2 B1 1.496(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.387(3) . ?
C1 C6 1.392(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.400(3) . ?
C6 C7 1.472(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.328(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.472(2) . ?
C9 C10 1.393(3) . ?
C9 C13 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C11 1.446(3) 2_566 ?
C11 C12 1.428(3) . ?
C12 C13 1.412(3) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.524(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.529(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.525(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C11 122.30(16) . . ?
C10 N1 B1 113.84(15) . 2_566 ?
C11 N1 B1 123.76(15) . 2_566 ?
C12 N2 C14 119.65(15) . . ?
C12 N2 B1 124.94(16) . . ?
C14 N2 B1 115.41(15) . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C6 121.2(2) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.08(19) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.35(18) . . ?
C1 C6 C7 118.67(19) . . ?
C5 C6 C7 122.98(19) . . ?
C6 C7 H7 116.2 . . ?
C8 C7 C6 127.66(18) . . ?
C8 C7 H7 116.2 . . ?
C7 C8 H8 117.9 . . ?
C7 C8 C9 124.15(18) . . ?
C9 C8 H8 117.9 . . ?
C10 C9 C8 118.62(17) . . ?
C13 C9 C8 123.38(18) . . ?
C13 C9 C10 117.98(17) . . ?
N1 C10 C9 121.14(17) . . ?
N1 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
N1 C11 C11 118.2(2) . 2_566 ?
N1 C11 C12 119.56(16) . . ?
C12 C11 C11 122.2(2) . 2_566 ?
N2 C12 C11 120.09(16) . . ?
N2 C12 C13 122.81(17) . . ?
C13 C12 C11 117.09(17) . . ?
C9 C13 C12 121.93(18) . . ?
C9 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
N2 C14 H14A 109.1 . . ?
N2 C14 H14B 109.1 . . ?
N2 C14 C15 112.50(17) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C14 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C14 C15 C16 113.14(19) . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C15 112.5(2) . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
F1 B1 N1 106.78(18) . 2_566 ?
F1 B1 N2 111.73(17) . . ?
F2 B1 F1 108.54(18) . . ?
F2 B1 N1 107.25(17) . 2_566 ?
F2 B1 N2 112.01(19) . . ?
N2 B1 N1 110.29(15) . 2_566 ?

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
N1 C11 C12 N2 179.23(17) . . . . ?
N1 C11 C12 C13 -0.1(3) . . . . ?
N2 C12 C13 C9 -178.84(18) . . . . ?
N2 C14 C15 C16 172.39(17) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C1 C6 C7 C8 -173.3(2) . . . . ?
C2 C1 C6 C5 0.0(4) . . . . ?
C2 C1 C6 C7 -179.6(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 179.6(2) . . . . ?
C5 C6 C7 C8 7.0(4) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C6 C7 C8 C9 178.82(19) . . . . ?
C7 C8 C9 C10 -162.2(2) . . . . ?
C7 C8 C9 C13 16.5(3) . . . . ?
C8 C9 C10 N1 178.40(17) . . . . ?
C8 C9 C13 C12 -178.95(18) . . . . ?
C10 N1 C11 C11 178.8(2) . . . 2_566 ?
C10 N1 C11 C12 -0.5(3) . . . . ?
C10 C9 C13 C12 -0.3(3) . . . . ?
C11 N1 C10 C9 0.7(3) . . . . ?
C11 C11 C12 N2 0.0(3) 2_566 . . . ?
C11 C11 C12 C13 -179.4(2) 2_566 . . . ?
C11 C12 C13 C9 0.5(3) . . . . ?
C12 N2 C14 C15 -79.3(2) . . . . ?
C12 N2 B1 F1 -111.4(2) . . . . ?
C12 N2 B1 F2 126.6(2) . . . . ?
C12 N2 B1 N1 7.2(3) . . . 2_566 ?
C13 C9 C10 N1 -0.3(3) . . . . ?
C14 N2 C12 C11 176.41(17) . . . . ?
C14 N2 C12 C13 -4.2(3) . . . . ?
C14 N2 B1 F1 68.3(2) . . . . ?
C14 N2 B1 F2 -53.7(2) . . . . ?
C14 N2 B1 N1 -173.06(16) . . . 2_566 ?
C14 C15 C16 C17 -79.2(3) . . . . ?
B1 N1 C10 C9 -175.74(18) 2_566 . . . ?
B1 N1 C11 C11 -5.1(3) 2_566 . . 2_566 ?
B1 N1 C11 C12 175.63(18) 2_566 . . . ?
B1 N2 C12 C11 -3.9(3) . . . . ?
B1 N2 C12 C13 175.44(19) . . . . ?
B1 N2 C14 C15 101.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
