# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_20240407
_database_code_depnum_ccdc_archive 'CCDC 2346296'
loop_
_audit_author_name
_audit_author_address
'Yuming Li'
;Tianjin University of Science and Technology
China
;
_audit_update_record             
;
2024-04-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_audit_creation_date             2024-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H17 N2 O S'
_chemical_formula_sum            'C24 H17 N2 O S'
_chemical_formula_weight         381.45
_chemical_absolute_configuration ?
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   19.8487(19)
_cell_length_b                   11.0122(12)
_cell_length_c                   8.5823(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1875.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4017
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.985
_cell_measurement_theta_min      3.009
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5856
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1668 before and 0.0723 after correction.
The Ratio of minimum to maximum transmission is 0.7856.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             796
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15262
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.381
_diffrn_reflns_theta_min         2.115
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2717
_reflns_number_total             3814
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 893 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(6)
_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     253
_refine_ls_number_reflns         3814
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.075
_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)+(0.0861P)²+0.7867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1583
_refine_ls_wR_factor_ref         0.1803
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22a,H22b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C5(H5), C4(H4), C3(H3), C17(H17), C13(H13), C15(H15),
 C24(H24), C14(H14), C16(H16), C23(H23)
;
_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 0.87483(10) 0.81704(19) 0.5987(3) 0.0699(6) Uani 1 1 d . . . . .
N1 N 0.6242(2) 0.3712(4) 0.5928(6) 0.0409(10) Uani 1 1 d . . . . .
O1 O 0.7551(3) 0.7301(5) 0.4112(5) 0.0610(13) Uani 1 1 d . . . . .
C22 C 0.8565(2) 0.6037(5) 0.7369(6) 0.0345(11) Uani 1 1 d . . . . .
H22A H 0.8255 0.5890 0.8223 0.041 Uiso 1 1 calc R . . . .
H22B H 0.8673 0.5269 0.6876 0.041 Uiso 1 1 calc R . . . .
C12 C 0.7797(3) 0.4303(6) 0.3767(6) 0.0399(13) Uani 1 1 d . . . . .
N2 N 0.6915(3) 0.5609(6) 0.8729(7) 0.0649(16) Uani 1 1 d . . . . .
C1 C 0.5687(3) 0.3133(5) 0.6540(6) 0.0398(13) Uani 1 1 d . . . . .
C11 C 0.6951(2) 0.3399(5) 0.5721(7) 0.0394(13) Uani 1 1 d . . . . .
H11A H 0.7002 0.2670 0.5099 0.047 Uiso 1 1 calc R . . . .
H11B H 0.7174 0.3286 0.6716 0.047 Uiso 1 1 calc R . . . .
C8 C 0.6043(3) 0.4766(6) 0.5203(7) 0.0408(13) Uani 1 1 d . . . . .
C19 C 0.7026(3) 0.5668(5) 0.7424(7) 0.0427(13) Uani 1 1 d . . . . .
C9 C 0.6647(3) 0.5376(6) 0.4600(7) 0.0404(14) Uani 1 1 d . . . . .
H9 H 0.6620 0.5818 0.3611 0.048 Uiso 1 1 calc R . . . .
C10 C 0.7222(3) 0.4513(5) 0.4868(6) 0.0377(13) Uani 1 1 d . . . . .
C20 C 0.7671(3) 0.6708(6) 0.5280(7) 0.0434(13) Uani 1 1 d . . . . .
C6 C 0.5126(3) 0.3848(6) 0.6143(7) 0.0437(14) Uani 1 1 d . . . . .
C18 C 0.7186(3) 0.5730(5) 0.5785(7) 0.0403(13) Uani 1 1 d . . . . .
C7 C 0.5363(3) 0.4887(6) 0.5307(7) 0.0469(15) Uani 1 1 d . . . . .
H7 H 0.5104 0.5520 0.4914 0.056 Uiso 1 1 calc R . . . .
C2 C 0.5636(3) 0.2055(6) 0.7369(8) 0.0492(15) Uani 1 1 d . . . . .
H2 H 0.6013 0.1589 0.7605 0.059 Uiso 1 1 calc R . . . .
C21 C 0.8271(3) 0.6909(6) 0.6220(7) 0.0429(13) Uani 1 1 d . . . . .
C5 C 0.4485(3) 0.3457(7) 0.6611(8) 0.0525(17) Uani 1 1 d . . . . .
H5 H 0.4103 0.3903 0.6353 0.063 Uiso 1 1 calc R . . . .
C4 C 0.4432(3) 0.2407(8) 0.7454(8) 0.062(2) Uani 1 1 d . . . . .
H4 H 0.4009 0.2151 0.7787 0.074 Uiso 1 1 calc R . . . .
C3 C 0.4999(4) 0.1710(7) 0.7826(8) 0.0578(18) Uani 1 1 d . . . . .
H3 H 0.4944 0.0998 0.8394 0.069 Uiso 1 1 calc R . . . .
C17 C 0.8367(3) 0.3695(7) 0.4307(8) 0.0562(17) Uani 1 1 d . . . . .
H17 H 0.8389 0.3451 0.5343 0.067 Uiso 1 1 calc R . . . .
C13 C 0.7780(3) 0.4638(7) 0.2221(7) 0.0555(17) Uani 1 1 d . . . . .
H13 H 0.7408 0.5050 0.1827 0.067 Uiso 1 1 calc R . . . .
C15 C 0.8867(4) 0.3755(8) 0.1805(9) 0.070(2) Uani 1 1 d . . . . .
H15 H 0.9220 0.3551 0.1140 0.084 Uiso 1 1 calc R . . . .
C24 C 0.9311(3) 0.7736(7) 0.7269(10) 0.0635(19) Uani 1 1 d . . . . .
H24 H 0.9687 0.8200 0.7521 0.076 Uiso 1 1 calc R . . . .
C14 C 0.8321(4) 0.4358(8) 0.1249(8) 0.072(2) Uani 1 1 d . . . . .
H14 H 0.8307 0.4586 0.0206 0.087 Uiso 1 1 calc R . . . .
C16 C 0.8896(4) 0.3453(8) 0.3325(11) 0.071(2) Uani 1 1 d . . . . .
H16 H 0.9280 0.3075 0.3715 0.086 Uiso 1 1 calc R . . . .
C23 C 0.9181(4) 0.6658(8) 0.7922(9) 0.068(2) Uani 1 1 d . . . . .
H23 H 0.9461 0.6320 0.8675 0.082 Uiso 1 1 calc R . . . .


_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 C21 1.693(6) . ?
S1 C24 1.638(8) . ?
N1 C1 1.377(7) . ?
N1 C11 1.460(6) . ?
N1 C8 1.375(8) . ?
O1 C20 1.219(7) . ?
C22 C21 1.495(8) . ?
C22 C23 1.480(9) . ?
C12 C10 1.500(7) . ?
C12 C17 1.392(8) . ?
C12 C13 1.378(9) . ?
N2 C19 1.143(8) . ?
C1 C6 1.404(8) . ?
C1 C2 1.388(9) . ?
C11 C10 1.526(8) . ?
C8 C9 1.468(8) . ?
C8 C7 1.359(7) . ?
C19 C18 1.444(8) . ?
C9 C10 1.504(8) . ?
C9 C18 1.527(8) . ?
C10 C18 1.556(8) . ?
C20 C18 1.508(8) . ?
C20 C21 1.456(8) . ?
C6 C7 1.430(9) . ?
C6 C5 1.402(8) . ?
C2 C3 1.377(9) . ?
C5 C4 1.368(10) . ?
C4 C3 1.399(11) . ?
C17 C16 1.373(9) . ?
C13 C14 1.394(9) . ?
C15 C14 1.358(11) . ?
C15 C16 1.348(12) . ?
C24 C23 1.338(11) . ?

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
C24 S1 C21 93.6(4) . . ?
C1 N1 C11 135.1(5) . . ?
C8 N1 C1 109.5(4) . . ?
C8 N1 C11 114.9(4) . . ?
C23 C22 C21 103.7(5) . . ?
C17 C12 C10 118.9(5) . . ?
C13 C12 C10 123.1(5) . . ?
C13 C12 C17 118.0(6) . . ?
N1 C1 C6 106.3(5) . . ?
N1 C1 C2 130.5(5) . . ?
C2 C1 C6 123.1(5) . . ?
N1 C11 C10 102.1(4) . . ?
N1 C8 C9 108.2(4) . . ?
C7 C8 N1 109.7(5) . . ?
C7 C8 C9 142.1(6) . . ?
N2 C19 C18 178.3(7) . . ?
C8 C9 C10 106.1(5) . . ?
C8 C9 C18 117.0(5) . . ?
C10 C9 C18 61.8(4) . . ?
C12 C10 C11 116.5(5) . . ?
C12 C10 C9 125.4(5) . . ?
C12 C10 C18 119.1(5) . . ?
C11 C10 C18 115.6(4) . . ?
C9 C10 C11 108.2(4) . . ?
C9 C10 C18 59.9(4) . . ?
O1 C20 C18 119.6(5) . . ?
O1 C20 C21 122.2(6) . . ?
C21 C20 C18 118.1(5) . . ?
C1 C6 C7 108.0(5) . . ?
C5 C6 C1 118.5(6) . . ?
C5 C6 C7 133.5(6) . . ?
C19 C18 C9 118.9(5) . . ?
C19 C18 C10 117.6(5) . . ?
C19 C18 C20 117.0(5) . . ?
C9 C18 C10 58.4(4) . . ?
C20 C18 C9 116.0(5) . . ?
C20 C18 C10 116.1(5) . . ?
C8 C7 C6 106.3(5) . . ?
C3 C2 C1 116.6(6) . . ?
C22 C21 S1 112.8(4) . . ?
C20 C21 S1 121.1(5) . . ?
C20 C21 C22 125.9(5) . . ?
C4 C5 C6 118.8(6) . . ?
C5 C4 C3 121.4(6) . . ?
C2 C3 C4 121.5(7) . . ?
C16 C17 C12 120.7(7) . . ?
C12 C13 C14 119.8(7) . . ?
C16 C15 C14 119.6(7) . . ?
C23 C24 S1 114.2(6) . . ?
C15 C14 C13 120.9(7) . . ?
C15 C16 C17 120.9(8) . . ?
C24 C23 C22 115.8(7) . . ?

_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_240615lu_lgpz305045_0m
_database_code_depnum_ccdc_archive 'CCDC 2375873'
loop_
_audit_author_name
_audit_author_address
'Yuming Li'
;Tianjin University of Science and Technology
China
;
_audit_update_record             
;
2024-08-06 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_audit_creation_date             2024-06-16
_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         'C24 H16 Br N3, [+ solvents]'
_chemical_formula_sum            'C24 H16 Br N3'
_chemical_formula_weight         426.31
_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'
Br Br -0.2901 2.4595 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.132(3)
_cell_length_b                   17.534(3)
_cell_length_c                   12.433(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.296(7)
_cell_angle_gamma                90
_cell_volume                     2410.5(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3927
_cell_measurement_temperature    295.30
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.17
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    1.717
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.3887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1102 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.5216.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18458
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.368
_diffrn_reflns_theta_min         2.140
_diffrn_ambient_temperature      295.30
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2497
_reflns_number_total             4389
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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, 2019)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.045
_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)+(0.0627P)²+0.8894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1529
_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:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C10(H10), C18(H18), C17(H17), C3(H3), C2(H2), C14(H14), C23(H23),
 C21(H21), C11(H11), C13(H13), C12(H12), C22(H22)
2.d Fitted hexagon refined as free rotating group:
 C1(C18,C17,C4,C3,C2)
;
_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 0.64746(5) 0.36257(3) 0.41633(6) 0.0958(3) Uani 1 1 d . . . . .
N1 N 0.7144(3) 0.73004(17) 0.3261(3) 0.0519(8) Uani 1 1 d . . . . .
N2 N 0.8899(3) 0.73834(17) 0.4869(3) 0.0565(9) Uani 1 1 d . . . . .
N3 N 0.7421(4) 0.86674(19) 0.6580(3) 0.0700(10) Uani 1 1 d . . . . .
C5 C 0.5914(4) 0.7062(2) 0.4809(3) 0.0533(10) Uani 1 1 d . . . . .
H5 H 0.551011 0.715145 0.533696 0.064 Uiso 1 1 calc R U . . .
C7 C 0.7736(4) 0.74621(19) 0.4433(3) 0.0502(10) Uani 1 1 d . . . . .
C19 C 0.8018(4) 0.7093(2) 0.2873(3) 0.0549(11) Uani 1 1 d . . . . .
C6 C 0.6850(4) 0.7672(2) 0.4921(3) 0.0484(9) Uani 1 1 d . . . . .
C9 C 0.4647(4) 0.8232(2) 0.3707(3) 0.0563(11) Uani 1 1 d . . . . .
C8 C 0.5603(4) 0.76513(19) 0.3856(3) 0.0536(10) Uani 1 1 d . . . . .
C16 C 0.7184(4) 0.8230(2) 0.5847(3) 0.0524(10) Uani 1 1 d . . . . .
C20 C 0.9116(5) 0.7150(2) 0.3887(4) 0.0615(11) Uani 1 1 d . . . . .
C24 C 0.7985(5) 0.6865(2) 0.1782(4) 0.0711(14) Uani 1 1 d . . . . .
H24 H 0.726367 0.683628 0.111063 0.085 Uiso 1 1 calc R U . . .
C10 C 0.3505(4) 0.8000(3) 0.3545(4) 0.0674(12) Uani 1 1 d . . . . .
H10 H 0.333087 0.748246 0.352346 0.081 Uiso 1 1 calc R U . . .
C15 C 0.5859(4) 0.7455(2) 0.2771(3) 0.0617(11) Uani 1 1 d . . . . .
H15A H 0.540017 0.701070 0.236354 0.074 Uiso 1 1 calc R U . . .
H15B H 0.565670 0.787976 0.222427 0.074 Uiso 1 1 calc R U . . .
C1 C 0.6338(3) 0.46777(10) 0.4380(3) 0.0679(12) Uani 1 1 d G . . . .
C18 C 0.5273(2) 0.50498(14) 0.3673(2) 0.0803(14) Uani 1 1 d G . . . .
H18 H 0.464037 0.477802 0.310939 0.096 Uiso 1 1 calc R U . . .
C17 C 0.5154(2) 0.58281(14) 0.3810(2) 0.0780(14) Uani 1 1 d G . . . .
H17 H 0.444154 0.607705 0.333707 0.094 Uiso 1 1 calc R U . . .
C4 C 0.6100(2) 0.62343(10) 0.4652(2) 0.0528(10) Uani 1 1 d G . . . .
C3 C 0.7164(2) 0.58621(13) 0.5359(2) 0.0610(11) Uani 1 1 d G . . . .
H3 H 0.779702 0.613392 0.592273 0.073 Uiso 1 1 calc R U . . .
C2 C 0.7283(2) 0.50838(14) 0.5222(2) 0.0715(13) Uani 1 1 d G . . . .
H2 H 0.799587 0.483488 0.569506 0.086 Uiso 1 1 calc R U . . .
C14 C 0.4882(4) 0.9000(2) 0.3726(4) 0.0761(14) Uani 1 1 d . . . . .
H14 H 0.564376 0.916563 0.381627 0.091 Uiso 1 1 calc R U . . .
C23 C 0.9080(7) 0.6683(3) 0.1755(5) 0.0863(17) Uani 1 1 d . . . . .
H23 H 0.908967 0.651656 0.104914 0.104 Uiso 1 1 calc R U . . .
C21 C 1.0189(5) 0.6974(3) 0.3807(5) 0.0786(14) Uani 1 1 d . . . . .
H21 H 1.091812 0.701453 0.446758 0.094 Uiso 1 1 calc R U . . .
C11 C 0.2612(5) 0.8532(3) 0.3414(4) 0.0802(14) Uani 1 1 d . . . . .
H11 H 0.184036 0.837084 0.329576 0.096 Uiso 1 1 calc R U . . .
C13 C 0.3993(6) 0.9526(3) 0.3611(4) 0.0895(17) Uani 1 1 d . . . . .
H13 H 0.416642 1.004391 0.363786 0.107 Uiso 1 1 calc R U . . .
C12 C 0.2872(5) 0.9297(3) 0.3460(4) 0.0875(16) Uani 1 1 d . . . . .
H12 H 0.228134 0.965645 0.338828 0.105 Uiso 1 1 calc R U . . .
C22 C 1.0174(6) 0.6740(3) 0.2750(6) 0.0871(16) Uani 1 1 d . . . . .
H22 H 1.089544 0.661873 0.269470 0.105 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 C1 1.8810(18) . ?
N1 C7 1.363(4) . ?
N1 C19 1.383(5) . ?
N1 C15 1.446(5) . ?
N2 C7 1.294(5) . ?
N2 C20 1.411(5) . ?
N3 C16 1.134(4) . ?
C5 H5 0.9800 . ?
C5 C6 1.523(5) . ?
C5 C8 1.498(5) . ?
C5 C4 1.494(4) . ?
C7 C6 1.482(5) . ?
C19 C20 1.411(6) . ?
C19 C24 1.399(5) . ?
C6 C8 1.548(5) . ?
C6 C16 1.438(5) . ?
C9 C8 1.497(5) . ?
C9 C10 1.377(6) . ?
C9 C14 1.374(6) . ?
C8 C15 1.543(6) . ?
C20 C21 1.381(6) . ?
C24 H24 0.9300 . ?
C24 C23 1.379(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C1 C18 1.3900 . ?
C1 C2 1.3900 . ?
C18 H18 0.9300 . ?
C18 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C4 1.3900 . ?
C4 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C2 1.3900 . ?
C2 H2 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.382(6) . ?
C23 H23 0.9300 . ?
C23 C22 1.397(8) . ?
C21 H21 0.9300 . ?
C21 C22 1.370(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.355(7) . ?
C12 H12 0.9300 . ?
C22 H22 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 N1 C19 106.5(3) . . ?
C7 N1 C15 114.5(3) . . ?
C19 N1 C15 138.6(3) . . ?
C7 N2 C20 103.2(3) . . ?
C6 C5 H5 112.7 . . ?
C8 C5 H5 112.7 . . ?
C8 C5 C6 61.6(2) . . ?
C4 C5 H5 112.7 . . ?
C4 C5 C6 123.2(3) . . ?
C4 C5 C8 124.7(3) . . ?
N1 C7 C6 109.7(4) . . ?
N2 C7 N1 115.5(4) . . ?
N2 C7 C6 134.8(3) . . ?
N1 C19 C20 104.3(3) . . ?
N1 C19 C24 134.0(4) . . ?
C24 C19 C20 121.7(4) . . ?
C5 C6 C8 58.4(2) . . ?
C7 C6 C5 115.3(3) . . ?
C7 C6 C8 105.2(3) . . ?
C16 C6 C5 120.3(3) . . ?
C16 C6 C7 119.0(4) . . ?
C16 C6 C8 123.7(3) . . ?
C10 C9 C8 119.9(4) . . ?
C14 C9 C8 121.3(4) . . ?
C14 C9 C10 118.8(4) . . ?
C5 C8 C6 60.0(2) . . ?
C5 C8 C15 117.5(3) . . ?
C6 C8 C15 106.0(3) . . ?
C9 C8 C5 119.9(4) . . ?
C9 C8 C6 121.7(3) . . ?
C9 C8 C15 117.9(3) . . ?
N3 C16 C6 178.3(5) . . ?
C19 C20 N2 110.5(4) . . ?
C21 C20 N2 130.1(5) . . ?
C21 C20 C19 119.4(4) . . ?
C19 C24 H24 121.7 . . ?
C23 C24 C19 116.5(5) . . ?
C23 C24 H24 121.7 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
N1 C15 C8 104.1(3) . . ?
N1 C15 H15A 110.9 . . ?
N1 C15 H15B 110.9 . . ?
C8 C15 H15A 110.9 . . ?
C8 C15 H15B 110.9 . . ?
H15A C15 H15B 109.0 . . ?
C18 C1 Br1 118.92(16) . . ?
C18 C1 C2 120.0 . . ?
C2 C1 Br1 121.08(16) . . ?
C1 C18 H18 120.0 . . ?
C1 C18 C17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C4 C17 C18 120.0 . . ?
C4 C17 H17 120.0 . . ?
C17 C4 C5 118.3(2) . . ?
C17 C4 C3 120.0 . . ?
C3 C4 C5 121.6(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C9 C14 H14 119.9 . . ?
C9 C14 C13 120.3(5) . . ?
C13 C14 H14 119.9 . . ?
C24 C23 H23 118.8 . . ?
C24 C23 C22 122.4(5) . . ?
C22 C23 H23 118.8 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.7(5) . . ?
C22 C21 H21 120.1 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(5) . . ?
C12 C11 H11 120.1 . . ?
C14 C13 H13 119.5 . . ?
C12 C13 C14 120.9(5) . . ?
C12 C13 H13 119.5 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(5) . . ?
C13 C12 H12 120.2 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.2(5) . . ?
C21 C22 H22 119.9 . . ?

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 C1 C18 C17 -179.5(2) . . . . ?
Br1 C1 C2 C3 179.5(2) . . . . ?
N1 C7 C6 C5 59.4(4) . . . . ?
N1 C7 C6 C8 -2.4(4) . . . . ?
N1 C7 C6 C16 -146.4(3) . . . . ?
N1 C19 C20 N2 0.3(4) . . . . ?
N1 C19 C20 C21 179.6(4) . . . . ?
N1 C19 C24 C23 -178.4(4) . . . . ?
N2 C7 C6 C5 -118.4(5) . . . . ?
N2 C7 C6 C8 179.7(4) . . . . ?
N2 C7 C6 C16 35.8(6) . . . . ?
N2 C20 C21 C22 178.5(4) . . . . ?
C5 C6 C8 C9 108.6(4) . . . . ?
C5 C6 C8 C15 -112.9(3) . . . . ?
C5 C8 C15 N1 -58.3(4) . . . . ?
C5 C4 C3 C2 177.1(3) . . . . ?
C7 N1 C19 C20 0.0(4) . . . . ?
C7 N1 C19 C24 179.6(4) . . . . ?
C7 N1 C15 C8 -7.9(4) . . . . ?
C7 N2 C20 C19 -0.5(4) . . . . ?
C7 N2 C20 C21 -179.7(4) . . . . ?
C7 C6 C8 C5 110.7(3) . . . . ?
C7 C6 C8 C9 -140.7(4) . . . . ?
C7 C6 C8 C15 -2.2(4) . . . . ?
C19 N1 C7 N2 -0.3(4) . . . . ?
C19 N1 C7 C6 -178.6(3) . . . . ?
C19 N1 C15 C8 179.9(4) . . . . ?
C19 C20 C21 C22 -0.7(6) . . . . ?
C19 C24 C23 C22 -1.6(7) . . . . ?
C6 C5 C8 C9 -111.6(4) . . . . ?
C6 C5 C8 C15 93.3(4) . . . . ?
C6 C5 C4 C17 -135.1(3) . . . . ?
C6 C5 C4 C3 47.8(4) . . . . ?
C6 C8 C15 N1 5.7(4) . . . . ?
C9 C8 C15 N1 146.1(4) . . . . ?
C9 C10 C11 C12 -0.8(7) . . . . ?
C9 C14 C13 C12 -1.0(7) . . . . ?
C8 C5 C6 C7 -92.9(3) . . . . ?
C8 C5 C6 C16 113.2(4) . . . . ?
C8 C5 C4 C17 -58.9(5) . . . . ?
C8 C5 C4 C3 124.0(4) . . . . ?
C8 C9 C10 C11 179.5(4) . . . . ?
C8 C9 C14 C13 -178.6(4) . . . . ?
C16 C6 C8 C5 -107.6(4) . . . . ?
C16 C6 C8 C9 1.0(6) . . . . ?
C16 C6 C8 C15 139.5(4) . . . . ?
C20 N2 C7 N1 0.5(4) . . . . ?
C20 N2 C7 C6 178.2(4) . . . . ?
C20 C19 C24 C23 1.2(6) . . . . ?
C20 C21 C22 C23 0.4(7) . . . . ?
C24 C19 C20 N2 -179.4(3) . . . . ?
C24 C19 C20 C21 -0.1(6) . . . . ?
C24 C23 C22 C21 0.8(8) . . . . ?
C10 C9 C8 C5 -55.5(5) . . . . ?
C10 C9 C8 C6 -126.7(4) . . . . ?
C10 C9 C8 C15 99.4(5) . . . . ?
C10 C9 C14 C13 1.5(6) . . . . ?
C10 C11 C12 C13 1.2(7) . . . . ?
C15 N1 C7 N2 -174.9(3) . . . . ?
C15 N1 C7 C6 6.8(4) . . . . ?
C15 N1 C19 C20 172.6(4) . . . . ?
C15 N1 C19 C24 -7.8(8) . . . . ?
C1 C18 C17 C4 0.0 . . . . ?
C18 C1 C2 C3 0.0 . . . . ?
C18 C17 C4 C5 -177.2(3) . . . . ?
C18 C17 C4 C3 0.0 . . . . ?
C17 C4 C3 C2 0.0 . . . . ?
C4 C5 C6 C7 22.0(5) . . . . ?
C4 C5 C6 C8 114.8(4) . . . . ?
C4 C5 C6 C16 -131.9(4) . . . . ?
C4 C5 C8 C6 -112.5(4) . . . . ?
C4 C5 C8 C9 135.9(4) . . . . ?
C4 C5 C8 C15 -19.2(6) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C2 C1 C18 C17 0.0 . . . . ?
C14 C9 C8 C5 124.5(4) . . . . ?
C14 C9 C8 C6 53.4(5) . . . . ?
C14 C9 C8 C15 -80.5(5) . . . . ?
C14 C9 C10 C11 -0.6(6) . . . . ?
C14 C13 C12 C11 -0.3(8) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.083 0.000 0.583 317.3 90.2 '2 ?'
2 -0.796 0.500 -0.296 317.3 90.2 '2 ?'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
