# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_cu250427a
_database_code_depnum_ccdc_archive 'CCDC 2482388'
loop_
_audit_author_name
_audit_author_address
ab
;HZNU
China
;
_audit_update_record             
;
2025-08-23 deposited with the CCDC.	2025-10-22 downloaded from the CCDC.
;
_audit_creation_date             2025-04-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 B F2 N2 S'
_chemical_formula_sum            'C13 H9 B F2 N2 S'
_chemical_formula_weight         274.09
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.1127(3)
_cell_length_b                   9.1231(2)
_cell_length_c                   11.7692(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.5780(10)
_cell_angle_gamma                90
_cell_volume                     1191.98(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6809
_cell_measurement_temperature    302.00
_cell_measurement_theta_max      79.120
_cell_measurement_theta_min      7.984
_shelx_estimated_absorpt_T_max   0.786
_shelx_estimated_absorpt_T_min   0.751
_exptl_absorpt_coefficient_mu    2.526
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0907 before and 0.0424 after correction.
The Ratio of minimum to maximum transmission is 0.8874.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10923
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.230
_diffrn_reflns_theta_min         7.983
_diffrn_ambient_temperature      302.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'BrukerD8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2319
_reflns_number_total             2480
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.3063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1039
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12)
;
_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
S1 S 0.49717(4) 0.48094(4) 0.73479(4) 0.04942(16) Uani 1 1 d . . . . .
F1 F 0.67644(9) 0.84889(14) 0.54748(12) 0.0762(4) Uani 1 1 d . . . . .
F2 F 0.74594(10) 0.84787(11) 0.75693(12) 0.0697(3) Uani 1 1 d . . . . .
N1 N 0.82542(11) 0.67557(14) 0.65578(12) 0.0429(3) Uani 1 1 d . . . . .
N2 N 0.61069(10) 0.65664(12) 0.64881(10) 0.0373(3) Uani 1 1 d . . . . .
C1 C 0.88812(15) 0.7048(2) 0.58488(18) 0.0555(4) Uani 1 1 d . . . . .
H1 H 0.862811 0.767370 0.516851 0.067 Uiso 1 1 calc R U . . .
C2 C 0.99426(17) 0.6279(2) 0.6289(2) 0.0703(6) Uani 1 1 d . . . . .
H2 H 1.052274 0.628032 0.595741 0.084 Uiso 1 1 calc R U . . .
C3 C 0.99905(15) 0.5499(2) 0.7319(2) 0.0656(5) Uani 1 1 d . . . . .
H3 H 1.061657 0.489682 0.781666 0.079 Uiso 1 1 calc R U . . .
C4 C 0.89296(13) 0.57849(18) 0.74725(15) 0.0481(4) Uani 1 1 d . . . . .
C5 C 0.85114(16) 0.50876(19) 0.82974(15) 0.0521(4) Uani 1 1 d . . . . .
H5 H 0.910230 0.461132 0.896186 0.063 Uiso 1 1 calc R U . . .
C6 C 0.73867(16) 0.50036(18) 0.82730(15) 0.0502(4) Uani 1 1 d . . . . .
H6 H 0.732308 0.452161 0.894051 0.060 Uiso 1 1 calc R U . . .
C006 C 0.48734(12) 0.67756(15) 0.57424(12) 0.0375(3) Uani 1 1 d . . . . .
C7 C 0.62850(13) 0.55538(16) 0.73629(13) 0.0403(3) Uani 1 1 d . . . . .
C8 C 0.41263(13) 0.58988(16) 0.61062(14) 0.0416(3) Uani 1 1 d . . . . .
C9 C 0.28732(14) 0.59614(18) 0.55098(16) 0.0515(4) Uani 1 1 d . . . . .
H9 H 0.238788 0.537187 0.576391 0.062 Uiso 1 1 calc R U . . .
C10 C 0.23782(14) 0.6919(2) 0.45371(16) 0.0553(4) Uani 1 1 d . . . . .
H10 H 0.154549 0.698283 0.412391 0.066 Uiso 1 1 calc R U . . .
C11 C 0.31107(16) 0.7790(2) 0.41669(16) 0.0555(4) Uani 1 1 d . . . . .
H11 H 0.275594 0.843005 0.350493 0.067 Uiso 1 1 calc R U . . .
C12 C 0.43527(14) 0.77377(18) 0.47507(15) 0.0482(3) Uani 1 1 d . . . . .
H12 H 0.482957 0.833060 0.448782 0.058 Uiso 1 1 calc R U . . .
B1 B 0.71662(15) 0.76317(19) 0.65115(18) 0.0460(4) 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
S1 C7 1.7232(15) . ?
S1 C8 1.7248(16) . ?
F1 B1 1.365(2) . ?
F2 B1 1.385(2) . ?
N1 C1 1.360(2) . ?
N1 C4 1.381(2) . ?
N1 B1 1.524(2) . ?
N2 C006 1.4107(18) . ?
N2 C7 1.3350(18) . ?
N2 B1 1.601(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.371(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(2) . ?
C4 C5 1.413(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.353(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.427(2) . ?
C006 C8 1.3972(19) . ?
C006 C12 1.393(2) . ?
C8 C9 1.395(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(2) . ?
C12 H12 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
C7 S1 C8 90.83(7) . . ?
C1 N1 C4 107.55(13) . . ?
C1 N1 B1 124.23(14) . . ?
C4 N1 B1 126.75(13) . . ?
C006 N2 B1 124.79(12) . . ?
C7 N2 C006 112.19(11) . . ?
C7 N2 B1 121.71(12) . . ?
N1 C1 H1 125.1 . . ?
N1 C1 C2 109.73(18) . . ?
C2 C1 H1 125.1 . . ?
C1 C2 H2 126.4 . . ?
C1 C2 C3 107.29(16) . . ?
C3 C2 H2 126.4 . . ?
C2 C3 H3 126.3 . . ?
C2 C3 C4 107.43(17) . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C3 107.98(16) . . ?
N1 C4 C5 124.10(14) . . ?
C3 C4 C5 127.45(17) . . ?
C4 C5 H5 114.9 . . ?
C6 C5 C4 130.19(15) . . ?
C6 C5 H5 114.9 . . ?
C5 C6 H6 115.6 . . ?
C5 C6 C7 128.85(15) . . ?
C7 C6 H6 115.6 . . ?
C8 C006 N2 112.74(12) . . ?
C12 C006 N2 128.19(13) . . ?
C12 C006 C8 119.06(13) . . ?
N2 C7 S1 113.65(11) . . ?
N2 C7 C6 129.52(14) . . ?
C6 C7 S1 116.83(11) . . ?
C006 C8 S1 110.59(11) . . ?
C9 C8 S1 127.40(12) . . ?
C9 C8 C006 122.00(15) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 118.03(15) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.43(15) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 122.05(16) . . ?
C12 C11 H11 119.0 . . ?
C006 C12 H12 120.8 . . ?
C11 C12 C006 118.43(15) . . ?
C11 C12 H12 120.8 . . ?
F1 B1 F2 110.82(15) . . ?
F1 B1 N1 109.06(13) . . ?
F1 B1 N2 109.62(13) . . ?
F2 B1 N1 110.69(13) . . ?
F2 B1 N2 105.65(12) . . ?
N1 B1 N2 110.98(12) . . ?

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
S1 C8 C9 C10 179.60(12) . . . . ?
N1 C1 C2 C3 -1.0(2) . . . . ?
N1 C4 C5 C6 11.7(3) . . . . ?
N2 C006 C8 S1 -1.09(14) . . . . ?
N2 C006 C8 C9 178.46(13) . . . . ?
N2 C006 C12 C11 -178.27(14) . . . . ?
C1 N1 C4 C3 0.67(18) . . . . ?
C1 N1 C4 C5 -171.98(15) . . . . ?
C1 N1 B1 F1 14.3(2) . . . . ?
C1 N1 B1 F2 -107.91(17) . . . . ?
C1 N1 B1 N2 135.11(15) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
C2 C3 C4 N1 -1.3(2) . . . . ?
C2 C3 C4 C5 171.06(17) . . . . ?
C3 C4 C5 C6 -159.52(19) . . . . ?
C4 N1 C1 C2 0.21(19) . . . . ?
C4 N1 B1 F1 178.72(14) . . . . ?
C4 N1 B1 F2 56.6(2) . . . . ?
C4 N1 B1 N2 -60.4(2) . . . . ?
C4 C5 C6 C7 3.0(3) . . . . ?
C5 C6 C7 S1 160.91(15) . . . . ?
C5 C6 C7 N2 -18.1(3) . . . . ?
C006 N2 C7 S1 -0.71(15) . . . . ?
C006 N2 C7 C6 178.29(15) . . . . ?
C006 N2 B1 F1 -18.0(2) . . . . ?
C006 N2 B1 F2 101.43(15) . . . . ?
C006 N2 B1 N1 -138.55(13) . . . . ?
C006 C8 C9 C10 0.1(2) . . . . ?
C7 S1 C8 C006 0.59(11) . . . . ?
C7 S1 C8 C9 -178.93(14) . . . . ?
C7 N2 C006 C8 1.17(16) . . . . ?
C7 N2 C006 C12 179.77(14) . . . . ?
C7 N2 B1 F1 176.08(13) . . . . ?
C7 N2 B1 F2 -64.47(17) . . . . ?
C7 N2 B1 N1 55.55(18) . . . . ?
C8 S1 C7 N2 0.07(11) . . . . ?
C8 S1 C7 C6 -179.07(12) . . . . ?
C8 C006 C12 C11 0.3(2) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C006 -0.1(3) . . . . ?
C12 C006 C8 S1 -179.84(11) . . . . ?
C12 C006 C8 C9 -0.3(2) . . . . ?
B1 N1 C1 C2 167.20(16) . . . . ?
B1 N1 C4 C3 -165.90(15) . . . . ?
B1 N1 C4 C5 21.4(2) . . . . ?
B1 N2 C006 C8 -165.90(13) . . . . ?
B1 N2 C006 C12 12.7(2) . . . . ?
B1 N2 C7 S1 166.81(11) . . . . ?
B1 N2 C7 C6 -14.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo241224a
_database_code_depnum_ccdc_archive 'CCDC 2482389'
loop_
_audit_author_name
_audit_author_address
ab
;HZNU
China
;
_audit_update_record             
;
2025-08-23 deposited with the CCDC.	2025-10-22 downloaded from the CCDC.
;
_audit_creation_date             2024-12-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 B F2 N2 S'
_chemical_formula_sum            'C15 H13 B F2 N2 S'
_chemical_formula_weight         302.14
_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 0.0033 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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.9891(5)
_cell_length_b                   13.5514(10)
_cell_length_c                   14.4026(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.392(3)
_cell_angle_gamma                90
_cell_volume                     1358.06(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8633
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      30.540
_cell_measurement_theta_min      2.841
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_correction_T_min  0.6888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0957 before and 0.0662 after correction.
The Ratio of minimum to maximum transmission is 0.9221.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37543
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.522
_diffrn_reflns_theta_min         2.841
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.6
_diffrn_source_power             0.08
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3727
_reflns_number_total             5854
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         5854
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0717P)²+0.1966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1548
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_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
S1 S 0.74296(5) 0.38564(3) 0.60159(2) 0.04575(12) Uani 1 1 d . . . . .
F1 F 0.56283(14) 0.45262(7) 0.27790(6) 0.0603(3) Uani 1 1 d . . . . .
F2 F 0.88565(15) 0.42639(6) 0.28722(6) 0.0591(3) Uani 1 1 d . . . . .
N1 N 0.77414(15) 0.58642(8) 0.32159(7) 0.0366(2) Uani 1 1 d . . . . .
N2 N 0.73363(14) 0.42807(7) 0.42709(7) 0.0360(2) Uani 1 1 d . . . . .
C1 C 0.74239(16) 0.47003(9) 0.51169(8) 0.0371(2) Uani 1 1 d . . . . .
C2 C 0.74625(19) 0.57064(10) 0.53732(9) 0.0429(3) Uani 1 1 d . . . . .
H2 H 0.744551 0.583129 0.600728 0.052 Uiso 1 1 calc R U . . .
C3 C 0.75212(19) 0.65201(10) 0.48200(9) 0.0419(3) Uani 1 1 d . . . . .
H3 H 0.747020 0.711441 0.513973 0.050 Uiso 1 1 calc R U . . .
C4 C 0.76439(17) 0.66286(9) 0.38607(9) 0.0373(2) Uani 1 1 d . . . . .
C5 C 0.71987(18) 0.32421(9) 0.43217(9) 0.0392(2) Uani 1 1 d . . . . .
C6 C 0.6978(3) 0.25765(11) 0.35832(11) 0.0534(3) Uani 1 1 d . . . . .
H6 H 0.692925 0.279590 0.296962 0.064 Uiso 1 1 calc R U . . .
C7 C 0.6831(3) 0.15829(12) 0.37808(13) 0.0620(4) Uani 1 1 d . . . . .
H7 H 0.666043 0.113384 0.329179 0.074 Uiso 1 1 calc R U . . .
C8 C 0.6934(3) 0.12386(11) 0.46948(14) 0.0622(4) Uani 1 1 d . . . . .
H8 H 0.686473 0.056437 0.480716 0.075 Uiso 1 1 calc R U . . .
C9 C 0.7137(2) 0.18860(11) 0.54339(12) 0.0540(3) Uani 1 1 d . . . . .
H9 H 0.718942 0.166056 0.604564 0.065 Uiso 1 1 calc R U . . .
C10 C 0.72602(19) 0.28896(10) 0.52372(9) 0.0426(3) Uani 1 1 d . . . . .
C11 C 0.7871(2) 0.75322(9) 0.34075(10) 0.0434(3) Uani 1 1 d . . . . .
C12 C 0.8141(2) 0.73110(11) 0.24927(11) 0.0530(3) Uani 1 1 d . . . . .
H12 H 0.835030 0.776596 0.202942 0.064 Uiso 1 1 calc R U . . .
C13 C 0.8048(2) 0.62942(10) 0.23826(10) 0.0467(3) Uani 1 1 d . . . . .
C14 C 0.8157(3) 0.57451(13) 0.14944(11) 0.0667(5) Uani 1 1 d . . . . .
H14A H 0.921670 0.529198 0.156252 0.100 Uiso 1 1 calc R U . . .
H14B H 0.834078 0.620291 0.100192 0.100 Uiso 1 1 calc R U . . .
H14C H 0.698383 0.538631 0.134581 0.100 Uiso 1 1 calc R U . . .
C15 C 0.7831(3) 0.85460(11) 0.38177(12) 0.0548(4) Uani 1 1 d . . . . .
H15A H 0.671853 0.861284 0.415624 0.082 Uiso 1 1 calc R U . . .
H15B H 0.777824 0.902701 0.332662 0.082 Uiso 1 1 calc R U . . .
H15C H 0.896984 0.864828 0.423322 0.082 Uiso 1 1 calc R U . . .
B1 B 0.7382(2) 0.47527(10) 0.32658(9) 0.0385(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
S1 C1 1.7272(12) . ?
S1 C10 1.7215(14) . ?
F1 B1 1.3881(17) . ?
F2 B1 1.3899(16) . ?
N1 C4 1.3971(15) . ?
N1 C13 1.3690(16) . ?
N1 B1 1.5299(17) . ?
N2 C1 1.3408(15) . ?
N2 C5 1.4132(16) . ?
N2 B1 1.5856(17) . ?
C1 C2 1.4121(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.3632(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.4001(18) . ?
C4 C11 1.4037(18) . ?
C5 C6 1.3920(19) . ?
C5 C10 1.3993(18) . ?
C6 H6 0.9300 . ?
C6 C7 1.382(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.392(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.394(2) . ?
C11 C12 1.381(2) . ?
C11 C15 1.4967(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(2) . ?
C13 C14 1.488(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
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
C10 S1 C1 91.17(6) . . ?
C4 N1 B1 132.86(10) . . ?
C13 N1 C4 106.78(10) . . ?
C13 N1 B1 120.01(11) . . ?
C1 N2 C5 111.89(10) . . ?
C1 N2 B1 130.96(10) . . ?
C5 N2 B1 117.15(10) . . ?
N2 C1 S1 113.40(9) . . ?
N2 C1 C2 130.17(11) . . ?
C2 C1 S1 116.40(9) . . ?
C1 C2 H2 115.5 . . ?
C3 C2 C1 128.99(12) . . ?
C3 C2 H2 115.5 . . ?
C2 C3 H3 114.0 . . ?
C2 C3 C4 132.04(12) . . ?
C4 C3 H3 114.0 . . ?
N1 C4 C3 126.13(11) . . ?
N1 C4 C11 108.84(11) . . ?
C3 C4 C11 124.79(12) . . ?
C6 C5 N2 127.52(12) . . ?
C6 C5 C10 119.36(12) . . ?
C10 C5 N2 113.11(11) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 C5 118.62(14) . . ?
C7 C6 H6 120.7 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.54(16) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.67(14) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 121.0 . . ?
C8 C9 C10 117.95(14) . . ?
C10 C9 H9 121.0 . . ?
C5 C10 S1 110.38(10) . . ?
C9 C10 S1 127.74(11) . . ?
C9 C10 C5 121.85(13) . . ?
C4 C11 C15 127.59(13) . . ?
C12 C11 C4 106.60(11) . . ?
C12 C11 C15 125.80(13) . . ?
C11 C12 H12 125.8 . . ?
C11 C12 C13 108.38(13) . . ?
C13 C12 H12 125.8 . . ?
N1 C13 C12 109.39(12) . . ?
N1 C13 C14 124.46(13) . . ?
C12 C13 C14 126.09(13) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F1 B1 F2 109.99(11) . . ?
F1 B1 N1 109.58(11) . . ?
F1 B1 N2 106.22(10) . . ?
F2 B1 N1 108.59(11) . . ?
F2 B1 N2 105.04(10) . . ?
N1 B1 N2 117.23(10) . . ?

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
S1 C1 C2 C3 177.98(12) . . . . ?
N1 C4 C11 C12 -1.08(15) . . . . ?
N1 C4 C11 C15 178.80(13) . . . . ?
N2 C1 C2 C3 -3.8(2) . . . . ?
N2 C5 C6 C7 -178.67(15) . . . . ?
N2 C5 C10 S1 1.44(14) . . . . ?
N2 C5 C10 C9 179.71(13) . . . . ?
C1 S1 C10 C5 -0.20(10) . . . . ?
C1 S1 C10 C9 -178.35(14) . . . . ?
C1 N2 C5 C6 176.23(14) . . . . ?
C1 N2 C5 C10 -2.32(15) . . . . ?
C1 N2 B1 F1 -117.29(13) . . . . ?
C1 N2 B1 F2 126.16(13) . . . . ?
C1 N2 B1 N1 5.53(19) . . . . ?
C1 C2 C3 C4 -3.2(3) . . . . ?
C2 C3 C4 N1 -0.1(2) . . . . ?
C2 C3 C4 C11 -173.71(14) . . . . ?
C3 C4 C11 C12 173.50(13) . . . . ?
C3 C4 C11 C15 -6.6(2) . . . . ?
C4 N1 C13 C12 -0.09(16) . . . . ?
C4 N1 C13 C14 -177.16(16) . . . . ?
C4 N1 B1 F1 104.75(15) . . . . ?
C4 N1 B1 F2 -135.08(13) . . . . ?
C4 N1 B1 N2 -16.3(2) . . . . ?
C4 C11 C12 C13 1.02(18) . . . . ?
C5 N2 C1 S1 2.16(13) . . . . ?
C5 N2 C1 C2 -176.09(13) . . . . ?
C5 N2 B1 F1 63.39(13) . . . . ?
C5 N2 B1 F2 -53.15(14) . . . . ?
C5 N2 B1 N1 -173.78(10) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C6 C5 C10 S1 -177.24(11) . . . . ?
C6 C5 C10 C9 1.0(2) . . . . ?
C6 C7 C8 C9 1.7(3) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 S1 177.44(13) . . . . ?
C8 C9 C10 C5 -0.5(2) . . . . ?
C10 S1 C1 N2 -1.15(10) . . . . ?
C10 S1 C1 C2 177.35(10) . . . . ?
C10 C5 C6 C7 -0.2(2) . . . . ?
C11 C12 C13 N1 -0.59(19) . . . . ?
C11 C12 C13 C14 176.43(17) . . . . ?
C13 N1 C4 C3 -173.77(13) . . . . ?
C13 N1 C4 C11 0.72(14) . . . . ?
C13 N1 B1 F1 -67.46(15) . . . . ?
C13 N1 B1 F2 52.70(16) . . . . ?
C13 N1 B1 N2 171.45(12) . . . . ?
C15 C11 C12 C13 -178.87(14) . . . . ?
B1 N1 C4 C3 13.3(2) . . . . ?
B1 N1 C4 C11 -172.24(12) . . . . ?
B1 N1 C13 C12 173.96(13) . . . . ?
B1 N1 C13 C14 -3.1(2) . . . . ?
B1 N2 C1 S1 -177.19(10) . . . . ?
B1 N2 C1 C2 4.6(2) . . . . ?
B1 N2 C5 C6 -4.33(19) . . . . ?
B1 N2 C5 C10 177.12(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
