# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_w5-2m_1211-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2313274'
loop_
_audit_author_name
_audit_author_address
'Frank Allen'
;lanzhou Data Centre
Australia
;
_audit_update_record             
;
2023-12-11 deposited with the CCDC.	2024-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 Br F5 N2'
_chemical_formula_weight         369.14

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'
Br Br -0.6763 1.2805 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

_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, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   17.6937(9)
_cell_length_b                   4.5126(2)
_cell_length_c                   18.7442(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.041(5)
_cell_angle_gamma                90
_cell_volume                     1445.35(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    4.376
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8115
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.061
_diffrn_reflns_theta_max         77.171
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2870
_reflns_number_gt                2170
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1039P)²+0.8240P] 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         2870
_refine_ls_number_parameters     210
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1962
_refine_ls_wR_factor_gt          0.1805
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.139
_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
Br1 Br 0.86987(3) 0.12270(15) 0.67550(3) 0.0859(3) Uani 1 1 d . . . . .
F1 F 0.49736(19) 0.3181(6) 0.43496(17) 0.0780(8) Uani 1 1 d . . . . .
F2 F 0.5571(2) -0.0886(6) 0.4303(2) 0.0873(9) Uani 1 1 d . . . . .
F3 F 0.45672(19) 0.0284(8) 0.34359(18) 0.0907(9) Uani 1 1 d . . . . .
F4 F 0.5749(4) 0.4838(14) 0.1331(3) 0.1084(16) Uani 0.7 1 d . U P A 1
F4B F 0.5674(9) 0.687(4) 0.1485(9) 0.110(4) Uani 0.3 1 d . U P A 2
F5 F 0.6133(5) 0.8730(14) 0.1812(4) 0.0860(17) Uani 0.5 1 d . U P A 1
F5B F 0.6638(6) 0.8787(15) 0.2029(5) 0.096(2) Uani 0.5 1 d . U P A 2
N1 N 0.6486(2) 0.3380(7) 0.37412(19) 0.0556(8) Uani 1 1 d . . . . .
N2 N 0.6787(2) 0.4588(9) 0.3213(2) 0.0628(9) Uani 1 1 d . . . . .
C1 C 0.5710(2) 0.2831(8) 0.3472(2) 0.0522(8) Uani 1 1 d . . . . .
C2 C 0.7685(3) 0.1273(9) 0.4508(3) 0.0611(10) Uani 1 1 d . . . . .
H2 H 0.779760 0.056330 0.408171 0.073 Uiso 1 1 calc R U . . .
C3 C 0.8950(3) -0.0905(15) 0.5236(4) 0.0911(17) Uani 1 1 d . . . . .
H3A H 0.893642 -0.176923 0.476503 0.137 Uiso 1 1 calc R U . . .
H3B H 0.900758 -0.244200 0.560041 0.137 Uiso 1 1 calc R U . . .
H3C H 0.938513 0.043611 0.537522 0.137 Uiso 1 1 calc R U . . .
C4 C 0.7312(3) 0.3422(9) 0.5777(2) 0.0587(9) Uani 1 1 d . . . . .
C5 C 0.6329(4) 0.5965(12) 0.1924(3) 0.0758(13) Uani 1 1 d . . . . .
H5A H 0.685897 0.555918 0.188052 0.091 Uiso 0.5 1 calc R U P A 1
H5B H 0.662346 0.460643 0.168940 0.091 Uiso 0.5 1 calc R U P A 2
C6 C 0.5496(3) 0.3731(9) 0.2754(2) 0.0589(10) Uani 1 1 d . . . . .
H6 H 0.500285 0.365054 0.242458 0.071 Uiso 1 1 calc R U . . .
C7 C 0.8201(3) 0.0760(10) 0.5186(3) 0.0645(10) Uani 1 1 d . . . . .
C8 C 0.6190(3) 0.4802(10) 0.2626(2) 0.0616(10) Uani 1 1 d . . . . .
C9 C 0.8001(3) 0.1877(10) 0.5807(2) 0.0598(10) Uani 1 1 d . . . . .
C10 C 0.7001(2) 0.2836(9) 0.4459(2) 0.0549(9) Uani 1 1 d . . . . .
C11 C 0.7098(4) 0.4572(15) 0.6450(3) 0.0844(15) Uani 1 1 d . . . . .
H11A H 0.661497 0.564964 0.630242 0.127 Uiso 1 1 calc R U . . .
H11B H 0.750456 0.586227 0.671836 0.127 Uiso 1 1 calc R U . . .
H11C H 0.703878 0.293906 0.675891 0.127 Uiso 1 1 calc R U . . .
C12 C 0.6816(3) 0.3906(9) 0.5079(2) 0.0588(10) Uani 1 1 d . . . . .
H12 H 0.635496 0.496576 0.503112 0.071 Uiso 1 1 calc R U . . .
C13 C 0.5211(3) 0.1378(8) 0.3895(3) 0.0580(9) 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
Br1 C9 1.905(4) . ?
F1 C13 1.323(5) . ?
F2 C13 1.335(5) . ?
F3 C13 1.332(5) . ?
F4 C5 1.398(9) . ?
F4B C5 1.301(16) . ?
F5 C5 1.297(8) . ?
F5B C5 1.380(9) . ?
N1 N2 1.354(5) . ?
N1 C1 1.357(5) . ?
N1 C10 1.436(5) . ?
N2 C8 1.317(6) . ?
C1 C6 1.363(6) . ?
C1 C13 1.483(6) . ?
C2 C7 1.378(7) . ?
C2 C10 1.383(6) . ?
C2 H2 0.9300 . ?
C3 C7 1.506(7) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C12 1.390(6) . ?
C4 C9 1.393(6) . ?
C4 C11 1.500(7) . ?
C5 C8 1.495(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 C8 1.396(7) . ?
C6 H6 0.9300 . ?
C7 C9 1.395(7) . ?
C10 C12 1.375(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
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
N2 N1 C1 110.8(3) . . ?
N2 N1 C10 118.6(3) . . ?
C1 N1 C10 130.7(3) . . ?
C8 N2 N1 104.9(4) . . ?
N1 C1 C6 107.9(4) . . ?
N1 C1 C13 124.6(4) . . ?
C6 C1 C13 127.5(4) . . ?
C7 C2 C10 120.5(4) . . ?
C7 C2 H2 119.8 . . ?
C10 C2 H2 119.8 . . ?
C7 C3 H3A 109.5 . . ?
C7 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C7 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C12 C4 C9 116.6(4) . . ?
C12 C4 C11 120.1(4) . . ?
C9 C4 C11 123.2(4) . . ?
F4B C5 F5B 93.2(8) . . ?
F5 C5 F4 96.4(6) . . ?
F5 C5 C8 112.5(5) . . ?
F4B C5 C8 110.1(8) . . ?
F5B C5 C8 110.4(5) . . ?
F4 C5 C8 108.5(5) . . ?
F5 C5 H5A 112.8 . . ?
F4 C5 H5A 112.8 . . ?
C8 C5 H5A 112.8 . . ?
F4B C5 H5B 113.8 . . ?
F5B C5 H5B 113.8 . . ?
C8 C5 H5B 113.8 . . ?
C1 C6 C8 104.0(4) . . ?
C1 C6 H6 128.0 . . ?
C8 C6 H6 128.0 . . ?
C2 C7 C9 117.2(4) . . ?
C2 C7 C3 120.2(5) . . ?
C9 C7 C3 122.5(5) . . ?
N2 C8 C6 112.4(4) . . ?
N2 C8 C5 118.8(4) . . ?
C6 C8 C5 128.7(4) . . ?
C4 C9 C7 123.7(4) . . ?
C4 C9 Br1 117.6(3) . . ?
C7 C9 Br1 118.6(3) . . ?
C12 C10 C2 121.2(4) . . ?
C12 C10 N1 119.9(4) . . ?
C2 C10 N1 118.8(4) . . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 C4 120.7(4) . . ?
C10 C12 H12 119.6 . . ?
C4 C12 H12 119.6 . . ?
F1 C13 F3 106.4(4) . . ?
F1 C13 F2 106.6(4) . . ?
F3 C13 F2 106.7(3) . . ?
F1 C13 C1 113.9(3) . . ?
F3 C13 C1 110.3(4) . . ?
F2 C13 C1 112.5(4) . . ?

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
C1 N1 N2 C8 0.7(5) . . . . ?
C10 N1 N2 C8 179.6(4) . . . . ?
N2 N1 C1 C6 -0.7(5) . . . . ?
C10 N1 C1 C6 -179.4(4) . . . . ?
N2 N1 C1 C13 176.9(4) . . . . ?
C10 N1 C1 C13 -1.8(7) . . . . ?
N1 C1 C6 C8 0.4(4) . . . . ?
C13 C1 C6 C8 -177.1(4) . . . . ?
C10 C2 C7 C9 0.0(7) . . . . ?
C10 C2 C7 C3 -179.1(5) . . . . ?
N1 N2 C8 C6 -0.5(5) . . . . ?
N1 N2 C8 C5 -177.7(4) . . . . ?
C1 C6 C8 N2 0.1(5) . . . . ?
C1 C6 C8 C5 177.0(5) . . . . ?
F5 C5 C8 N2 -100.2(7) . . . . ?
F4B C5 C8 N2 -160.6(9) . . . . ?
F5B C5 C8 N2 -59.1(7) . . . . ?
F4 C5 C8 N2 154.4(5) . . . . ?
F5 C5 C8 C6 83.0(8) . . . . ?
F4B C5 C8 C6 22.7(10) . . . . ?
F5B C5 C8 C6 124.2(6) . . . . ?
F4 C5 C8 C6 -22.4(7) . . . . ?
C12 C4 C9 C7 -1.6(7) . . . . ?
C11 C4 C9 C7 179.0(5) . . . . ?
C12 C4 C9 Br1 179.1(3) . . . . ?
C11 C4 C9 Br1 -0.2(6) . . . . ?
C2 C7 C9 C4 1.0(7) . . . . ?
C3 C7 C9 C4 -180.0(5) . . . . ?
C2 C7 C9 Br1 -179.8(3) . . . . ?
C3 C7 C9 Br1 -0.8(7) . . . . ?
C7 C2 C10 C12 -0.2(7) . . . . ?
C7 C2 C10 N1 178.7(4) . . . . ?
N2 N1 C10 C12 127.5(4) . . . . ?
C1 N1 C10 C12 -53.9(6) . . . . ?
N2 N1 C10 C2 -51.5(5) . . . . ?
C1 N1 C10 C2 127.1(5) . . . . ?
C2 C10 C12 C4 -0.5(7) . . . . ?
N1 C10 C12 C4 -179.4(4) . . . . ?
C9 C4 C12 C10 1.4(6) . . . . ?
C11 C4 C12 C10 -179.3(5) . . . . ?
N1 C1 C13 F1 80.7(5) . . . . ?
C6 C1 C13 F1 -102.2(5) . . . . ?
N1 C1 C13 F3 -159.7(4) . . . . ?
C6 C1 C13 F3 17.3(6) . . . . ?
N1 C1 C13 F2 -40.7(6) . . . . ?
C6 C1 C13 F2 136.3(4) . . . . ?

_refine_diff_density_max         0.623
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_rkw_0830-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2380999'
loop_
_audit_author_name
_audit_author_address
'ZHOU YUXIU'
;xibeishifandaxueceshizhongxin
China
;
_audit_update_record             
;
2024-08-31 deposited with the CCDC.	2024-11-14 downloaded from the CCDC.
;
_audit_creation_date             2024-08-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 Br F5 N2'
_chemical_formula_sum            'C17 H12 Br F5 N2'
_chemical_formula_weight         419.20
_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'
Br Br -0.6763 1.2805 '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'
N N 0.0311 0.0180 '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                   7.4520(4)
_cell_length_b                   10.0443(4)
_cell_length_c                   11.7716(5)
_cell_angle_alpha                86.890(3)
_cell_angle_beta                 73.961(4)
_cell_angle_gamma                70.172(4)
_cell_volume                     795.85(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8208
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.2640
_cell_measurement_theta_min      3.8830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.064
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8425
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.919
_diffrn_reflns_theta_min         3.911
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00  59.00   0.50    0.05    --  104.75 -61.00 -90.00   54
  2  ω    -19.00  28.00   0.50    0.05    --   46.68 -19.00-120.00   94
  3  ω    -21.00  27.00   0.50    0.05    --   46.68 -19.00 -30.00   96
  4  ω    -27.00  27.00   0.50    0.05    --   46.68 -19.00  30.00  108
  5  ω    -25.00  37.00   0.50    0.05    --   46.68 -37.00 120.00  124
  6  ω     75.00 103.00   0.50    0.05    --  104.75 -94.00 150.00   56
  7  ω     39.00  83.00   0.50    0.05    --  104.75-125.00  60.00   88
  8  ω     37.00 112.00   0.50    0.05    --  104.75-125.00 120.00  150
  9  ω     83.00 110.00   0.50    0.05    --  104.75-125.00  30.00   54
 10  ω     79.00 111.00   0.50    0.05    --  104.75-125.00   0.00   64
 11  ω     46.00  71.00   0.50    0.05    --  104.75-125.00  30.00   50
 12  ω     72.00 110.00   0.50    0.05    --  104.75-125.00 -90.00   76
 13  ω     35.00  68.00   0.50    0.05    --  104.75-125.00 -90.00   66
 14  ω     46.00 112.00   0.50    0.05    --  104.75-125.00-180.00  132
 15  ω     36.00  69.00   0.50    0.05    --   46.68-125.00-180.00   66
 16  ω    -25.00  77.00   0.50    0.05    --   46.68 -94.00  36.00  204
 17  ω     65.00  99.00   0.50    0.05    --  104.75 -94.00  90.00   68
 18  ω     69.00  95.00   0.50    0.05    --  104.75 -94.00  36.00   52
 19  ω     93.00 172.00   0.50    0.05    --  104.75  45.00 120.00  158
 20  ω    112.00 137.00   0.50    0.05    --  104.75  94.00 146.00   50
 21  ω    144.00 169.00   0.50    0.05    --  104.75  77.00-180.00   50
 22  ω     82.00 136.00   0.50    0.05    --  104.75  77.00-180.00  108
 23  ω    -83.00 -40.00   0.50    0.05    -- -102.00  77.00 -30.00   86
 24  ω    -67.00 -30.00   0.50    0.05    -- -102.00  61.00  90.00   74
 25  ω    -67.00 -41.00   0.50    0.05    -- -102.00  61.00-120.00   52
 26  ω    -67.00 -35.00   0.50    0.05    -- -102.00  61.00-150.00   64
 27  ω   -100.00 -32.00   0.50    0.05    -- -102.00 125.00-120.00  136
 28  ω    -29.00   8.00   0.50    0.05    --  -46.68  94.00 146.00   74
 29  ω    -77.00 -51.00   0.50    0.05    -- -102.00  94.00 146.00   52
 30  ω   -175.00 -90.00   0.50    0.05    -- -102.00 -61.00 -90.00  170
 31  ω   -127.00 -89.00   0.50    0.05    -- -102.00 -45.00 -30.00   76
 32  ω   -159.00-131.00   0.50    0.05    -- -102.00 -45.00 -30.00   56
 33  ω   -133.00 -84.00   0.50    0.05    -- -102.00 -77.00 120.00   98
 34  ω   -174.00-116.00   0.50    0.05    -- -102.00 -94.00 120.00  116
 35  ω   -157.00 -84.00   0.50    0.05    -- -102.00 -94.00  36.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1416059000
_diffrn_orient_matrix_UB_12      -0.1524145000
_diffrn_orient_matrix_UB_13      0.0023075000
_diffrn_orient_matrix_UB_21      0.1220293000
_diffrn_orient_matrix_UB_22      0.0121227000
_diffrn_orient_matrix_UB_23      -0.1267390000
_diffrn_orient_matrix_UB_31      0.1314843000
_diffrn_orient_matrix_UB_32      0.0570649000
_diffrn_orient_matrix_UB_33      0.0500981000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3093
_reflns_number_total             3125
_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       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.076
_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)+(0.0370P)²+0.8019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0750
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C8(H8), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17)
;
_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
Br1 Br 0.27356(3) 0.35532(2) 0.67800(2) 0.02557(9) Uani 1 1 d . . . . .
F1 F 0.39870(17) 0.93359(13) 0.76590(11) 0.0260(3) Uani 1 1 d . . . . .
F2 F 0.9209(2) 0.83498(15) 1.08198(12) 0.0349(3) Uani 1 1 d . . . . .
F3 F 1.19768(18) 0.71749(16) 0.95813(12) 0.0327(3) Uani 1 1 d . . . . .
F4 F 0.46847(18) 0.90225(14) 0.93274(10) 0.0265(3) Uani 1 1 d . . . . .
F5 F 0.52938(19) 1.06974(12) 0.82346(11) 0.0270(3) Uani 1 1 d . . . . .
N1 N 0.7535(2) 0.68685(17) 0.79622(14) 0.0174(3) Uani 1 1 d . . . . .
N2 N 0.8340(2) 0.64630(18) 0.89099(14) 0.0185(3) Uani 1 1 d . . . . .
C1 C 0.6413(3) 0.6106(2) 0.77001(16) 0.0162(4) Uani 1 1 d . . . . .
C2 C 0.9631(4) 0.8567(3) 0.38441(19) 0.0291(5) Uani 1 1 d . . . . .
H2 H 1.013347 0.860598 0.301289 0.035 Uiso 1 1 calc R U . . .
C3 C 1.0084(3) 0.7200(2) 1.00541(18) 0.0208(4) Uani 1 1 d . . . . .
H3 H 1.006150 0.631365 1.047918 0.025 Uiso 1 1 calc R U . . .
C4 C 0.8141(3) 0.8451(2) 0.62893(16) 0.0168(4) Uani 1 1 d . . . . .
C5 C 0.8879(3) 0.8580(2) 0.82716(18) 0.0206(4) Uani 1 1 d . . . . .
H5A H 1.017486 0.851079 0.771131 0.025 Uiso 1 1 calc R U . . .
H5B H 0.829564 0.951239 0.870614 0.025 Uiso 1 1 calc R U . . .
C6 C 0.7345(3) 0.9652(2) 0.56982(18) 0.0215(4) Uani 1 1 d . . . . .
H6 H 0.628984 1.044016 0.612773 0.026 Uiso 1 1 calc R U . . .
C7 C 0.8089(3) 0.9698(2) 0.44834(19) 0.0267(5) Uani 1 1 d . . . . .
H7 H 0.753142 1.051836 0.408701 0.032 Uiso 1 1 calc R U . . .
C8 C 0.5611(3) 0.6449(2) 0.67327(17) 0.0182(4) Uani 1 1 d . . . . .
H8 H 0.582672 0.719854 0.624887 0.022 Uiso 1 1 calc R U . . .
C9 C 0.4223(3) 0.4584(2) 0.71660(17) 0.0184(4) Uani 1 1 d . . . . .
C10 C 0.9068(3) 0.7386(2) 0.90996(17) 0.0184(4) Uani 1 1 d . . . . .
C11 C 0.9705(3) 0.7311(2) 0.56391(18) 0.0217(4) Uani 1 1 d . . . . .
H11 H 1.026975 0.648832 0.603096 0.026 Uiso 1 1 calc R U . . .
C12 C 0.7447(3) 0.8329(2) 0.76284(16) 0.0162(4) Uani 1 1 d . . . . .
C13 C 0.5327(3) 0.9352(2) 0.82088(17) 0.0199(4) Uani 1 1 d . . . . .
C14 C 0.6121(3) 0.4978(2) 0.83801(17) 0.0180(4) Uani 1 1 d . . . . .
H14 H 0.667122 0.472860 0.903170 0.022 Uiso 1 1 calc R U . . .
C15 C 1.0439(3) 0.7371(3) 0.4429(2) 0.0282(5) Uani 1 1 d . . . . .
H15 H 1.150201 0.658899 0.399562 0.034 Uiso 1 1 calc R U . . .
C16 C 0.4503(3) 0.5696(2) 0.64795(17) 0.0194(4) Uani 1 1 d . . . . .
H16 H 0.393629 0.594575 0.583431 0.023 Uiso 1 1 calc R U . . .
C17 C 0.5034(3) 0.4216(2) 0.81140(18) 0.0203(4) Uani 1 1 d . . . . .
H17 H 0.484728 0.344591 0.857908 0.024 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
Br1 C9 1.9007(19) . ?
F1 C13 1.336(2) . ?
F2 C3 1.360(2) . ?
F3 C3 1.358(2) . ?
F4 C13 1.336(2) . ?
F5 C13 1.345(2) . ?
N1 N2 1.388(2) . ?
N1 C1 1.408(3) . ?
N1 C12 1.483(2) . ?
N2 C10 1.278(3) . ?
C1 C8 1.402(3) . ?
C1 C14 1.395(3) . ?
C2 H2 0.9500 . ?
C2 C7 1.381(4) . ?
C2 C15 1.388(3) . ?
C3 H3 1.0000 . ?
C3 C10 1.490(3) . ?
C4 C6 1.394(3) . ?
C4 C11 1.397(3) . ?
C4 C12 1.529(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C10 1.498(3) . ?
C5 C12 1.557(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C16 1.388(3) . ?
C9 C16 1.383(3) . ?
C9 C17 1.387(3) . ?
C11 H11 0.9500 . ?
C11 C15 1.384(3) . ?
C12 C13 1.548(3) . ?
C14 H14 0.9500 . ?
C14 C17 1.388(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17 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
N2 N1 C1 118.18(15) . . ?
N2 N1 C12 111.54(15) . . ?
C1 N1 C12 127.07(15) . . ?
C10 N2 N1 108.63(16) . . ?
C8 C1 N1 120.47(17) . . ?
C14 C1 N1 120.61(17) . . ?
C14 C1 C8 118.91(18) . . ?
C7 C2 H2 120.4 . . ?
C7 C2 C15 119.3(2) . . ?
C15 C2 H2 120.4 . . ?
F2 C3 H3 110.8 . . ?
F2 C3 C10 109.87(16) . . ?
F3 C3 F2 104.96(17) . . ?
F3 C3 H3 110.8 . . ?
F3 C3 C10 109.54(16) . . ?
C10 C3 H3 110.8 . . ?
C6 C4 C11 118.80(18) . . ?
C6 C4 C12 123.47(18) . . ?
C11 C4 C12 117.69(17) . . ?
H5A C5 H5B 109.4 . . ?
C10 C5 H5A 111.6 . . ?
C10 C5 H5B 111.6 . . ?
C10 C5 C12 101.00(15) . . ?
C12 C5 H5A 111.6 . . ?
C12 C5 H5B 111.6 . . ?
C4 C6 H6 119.9 . . ?
C7 C6 C4 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 120.8(2) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C1 C8 H8 119.9 . . ?
C16 C8 C1 120.25(18) . . ?
C16 C8 H8 119.9 . . ?
C16 C9 Br1 119.02(15) . . ?
C16 C9 C17 120.44(18) . . ?
C17 C9 Br1 120.54(15) . . ?
N2 C10 C3 120.32(18) . . ?
N2 C10 C5 114.85(17) . . ?
C3 C10 C5 124.79(18) . . ?
C4 C11 H11 119.7 . . ?
C15 C11 C4 120.5(2) . . ?
C15 C11 H11 119.7 . . ?
N1 C12 C4 112.39(15) . . ?
N1 C12 C5 101.33(14) . . ?
N1 C12 C13 108.40(15) . . ?
C4 C12 C5 112.08(16) . . ?
C4 C12 C13 113.71(15) . . ?
C13 C12 C5 108.13(15) . . ?
F1 C13 F5 107.00(16) . . ?
F1 C13 C12 113.87(16) . . ?
F4 C13 F1 106.99(16) . . ?
F4 C13 F5 107.12(16) . . ?
F4 C13 C12 110.45(16) . . ?
F5 C13 C12 111.08(17) . . ?
C1 C14 H14 119.7 . . ?
C17 C14 C1 120.64(18) . . ?
C17 C14 H14 119.7 . . ?
C2 C15 H15 119.8 . . ?
C11 C15 C2 120.4(2) . . ?
C11 C15 H15 119.8 . . ?
C8 C16 H16 120.0 . . ?
C9 C16 C8 120.03(18) . . ?
C9 C16 H16 120.0 . . ?
C9 C17 C14 119.72(18) . . ?
C9 C17 H17 120.1 . . ?
C14 C17 H17 120.1 . . ?

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
Br1 C9 C16 C8 -178.94(14) . . . . ?
Br1 C9 C17 C14 179.80(14) . . . . ?
F2 C3 C10 N2 -123.6(2) . . . . ?
F2 C3 C10 C5 58.9(3) . . . . ?
F3 C3 C10 N2 121.6(2) . . . . ?
F3 C3 C10 C5 -55.9(3) . . . . ?
N1 N2 C10 C3 -178.43(17) . . . . ?
N1 N2 C10 C5 -0.7(2) . . . . ?
N1 C1 C8 C16 -179.86(17) . . . . ?
N1 C1 C14 C17 -179.27(17) . . . . ?
N1 C12 C13 F1 -77.1(2) . . . . ?
N1 C12 C13 F4 43.3(2) . . . . ?
N1 C12 C13 F5 162.05(15) . . . . ?
N2 N1 C1 C8 -178.30(17) . . . . ?
N2 N1 C1 C14 0.2(3) . . . . ?
N2 N1 C12 C4 135.75(16) . . . . ?
N2 N1 C12 C5 15.94(19) . . . . ?
N2 N1 C12 C13 -97.71(17) . . . . ?
C1 N1 N2 C10 -171.56(17) . . . . ?
C1 N1 C12 C4 -65.1(2) . . . . ?
C1 N1 C12 C5 175.11(17) . . . . ?
C1 N1 C12 C13 61.5(2) . . . . ?
C1 C8 C16 C9 -1.4(3) . . . . ?
C1 C14 C17 C9 -0.3(3) . . . . ?
C4 C6 C7 C2 -0.4(3) . . . . ?
C4 C11 C15 C2 0.1(3) . . . . ?
C4 C12 C13 F1 48.7(2) . . . . ?
C4 C12 C13 F4 169.10(16) . . . . ?
C4 C12 C13 F5 -72.2(2) . . . . ?
C5 C12 C13 F1 173.85(16) . . . . ?
C5 C12 C13 F4 -65.7(2) . . . . ?
C5 C12 C13 F5 53.0(2) . . . . ?
C6 C4 C11 C15 -0.5(3) . . . . ?
C6 C4 C12 N1 146.01(18) . . . . ?
C6 C4 C12 C5 -100.6(2) . . . . ?
C6 C4 C12 C13 22.4(3) . . . . ?
C7 C2 C15 C11 0.2(3) . . . . ?
C8 C1 C14 C17 -0.8(3) . . . . ?
C10 C5 C12 N1 -14.57(18) . . . . ?
C10 C5 C12 C4 -134.60(16) . . . . ?
C10 C5 C12 C13 99.28(17) . . . . ?
C11 C4 C6 C7 0.6(3) . . . . ?
C11 C4 C12 N1 -36.4(2) . . . . ?
C11 C4 C12 C5 77.0(2) . . . . ?
C11 C4 C12 C13 -159.98(17) . . . . ?
C12 N1 N2 C10 -10.3(2) . . . . ?
C12 N1 C1 C8 23.7(3) . . . . ?
C12 N1 C1 C14 -157.80(18) . . . . ?
C12 C4 C6 C7 178.25(19) . . . . ?
C12 C4 C11 C15 -178.22(19) . . . . ?
C12 C5 C10 N2 10.4(2) . . . . ?
C12 C5 C10 C3 -172.01(18) . . . . ?
C14 C1 C8 C16 1.6(3) . . . . ?
C15 C2 C7 C6 0.0(3) . . . . ?
C16 C9 C17 C14 0.5(3) . . . . ?
C17 C9 C16 C8 0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.378
_oxdiff_exptl_absorpt_empirical_full_min 0.689
