# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_cu_220603b_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2212548'
loop_
_audit_author_name
_audit_author_address
'pengfei sun'
;sundong university
China
;
_audit_update_record             
;
2022-10-12 deposited with the CCDC.	2023-03-05 downloaded from the CCDC.
;
_audit_creation_date             2022-06-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Br N3 S'
_chemical_formula_sum            'C21 H16 Br N3 S'
_chemical_formula_weight         422.34
_chemical_absolute_configuration syn
_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'
N N 0.0311 0.0180 '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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.8335(8)
_cell_length_b                   7.4016(10)
_cell_length_c                   11.2177(15)
_cell_angle_alpha                72.376(4)
_cell_angle_beta                 75.053(4)
_cell_angle_gamma                88.382(4)
_cell_volume                     445.34(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4765
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      4.28
_shelx_estimated_absorpt_T_max   0.813
_shelx_estimated_absorpt_T_min   0.752
_exptl_absorpt_coefficient_mu    4.308
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.1315
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1056 before and 0.0723 after correction.
The Ratio of minimum to maximum transmission is 0.4108.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             214
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4768
_diffrn_reflns_point_group_measured_fraction_full 0.841
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        66.497
_diffrn_reflns_theta_max         66.497
_diffrn_reflns_theta_min         4.285
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.712
_reflns_Friedel_fraction_max     0.712
_reflns_number_gt                2620
_reflns_number_total             2637
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 
;
 Flack x determined using 1093 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(14)
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2637
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.089
_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)+(0.0367P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0835
_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 Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.06094(2) 0.48478(2) 0.92307(2) 0.0341(2) Uani 1 1 d . . . . .
S1 S 0.8291(2) 0.6703(2) 0.41603(13) 0.0324(3) Uani 1 1 d . . . . .
N1 N 0.6298(8) 0.3863(7) 0.2086(4) 0.0342(10) Uani 1 1 d . . . . .
N2 N 0.7739(9) 0.2702(7) 0.2630(5) 0.0377(10) Uani 1 1 d . . . . .
N3 N 0.8527(7) 0.3520(6) 0.3377(4) 0.0333(9) Uani 1 1 d . . . . .
C1 C 0.1729(10) 0.6670(8) 0.6579(5) 0.0328(11) Uani 1 1 d . . . . .
H1 H 0.028372 0.727941 0.653879 0.039 Uiso 1 1 calc R U . . .
C2 C 0.9821(10) 0.0850(8) 0.7627(5) 0.0369(12) Uani 1 1 d . . . . .
H2 H 1.074005 0.092448 0.819876 0.044 Uiso 1 1 calc R U . . .
C3 C 0.3111(9) 0.6713(7) 0.1300(5) 0.0316(10) Uani 1 1 d . . . . .
H3 H 0.287935 0.547108 0.125730 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1975(9) 0.5416(7) 0.7720(5) 0.0300(10) Uani 1 1 d . . . . .
C5 C 0.5991(9) 0.4896(7) 0.6719(5) 0.0315(11) Uani 1 1 d . . . . .
H5 H 0.744355 0.430280 0.676810 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2060(11) 0.9966(9) 0.0840(6) 0.0377(14) Uani 1 1 d . . . . .
H6 H 0.107932 1.094089 0.052001 0.045 Uiso 1 1 calc R U . . .
C7 C 0.4812(8) 0.7054(7) 0.1891(5) 0.0277(10) Uani 1 1 d . . . . .
C8 C 1.0664(9) 0.1735(8) 0.6309(6) 0.0352(12) Uani 1 1 d . . . . .
H8 H 1.216676 0.241260 0.598163 0.042 Uiso 1 1 calc R U . . .
C9 C 0.4091(9) 0.4532(7) 0.7807(5) 0.0328(11) Uani 1 1 d . . . . .
H9 H 0.422769 0.368270 0.860918 0.039 Uiso 1 1 calc R U . . .
C10 C 0.3650(9) 0.7029(8) 0.5479(5) 0.0309(11) Uani 1 1 d . . . . .
H10 H 0.350931 0.788451 0.467929 0.037 Uiso 1 1 calc R U . . .
C11 C 0.7168(9) 0.0613(7) 0.5959(5) 0.0334(11) Uani 1 1 d . . . . .
H11 H 0.625992 0.052241 0.538581 0.040 Uiso 1 1 calc R U . . .
C12 C 0.5756(8) 0.6145(7) 0.5548(5) 0.0296(10) Uani 1 1 d . . . . .
C13 C 0.7604(8) 0.5266(7) 0.3299(5) 0.0302(10) Uani 1 1 d . . . . .
C14 C 0.6202(8) 0.5482(7) 0.2442(5) 0.0293(10) Uani 1 1 d . . . . .
C15 C 0.5168(9) 0.8914(7) 0.1913(5) 0.0330(11) Uani 1 1 d . . . . .
H15 H 0.634022 0.918680 0.229447 0.040 Uiso 1 1 calc R U . . .
C16 C 0.1748(9) 0.8149(8) 0.0771(5) 0.0354(11) Uani 1 1 d . . . . .
H16 H 0.060892 0.789101 0.036499 0.042 Uiso 1 1 calc R U . . .
C17 C 0.6304(10) -0.0279(8) 0.7266(6) 0.0349(14) Uani 1 1 d . . . . .
H17 H 0.481567 -0.097844 0.758711 0.042 Uiso 1 1 calc R U . . .
C18 C 0.9345(9) 0.1646(7) 0.5457(5) 0.0303(10) Uani 1 1 d . . . . .
C19 C 1.0317(11) 0.2600(10) 0.4017(6) 0.0391(15) Uani 1 1 d . . . . .
H19A H 1.158290 0.356046 0.388111 0.047 Uiso 1 1 calc R U . . .
H19B H 1.104797 0.163761 0.360751 0.047 Uiso 1 1 calc R U . . .
C20 C 0.7612(11) -0.0154(8) 0.8115(5) 0.0376(12) Uani 1 1 d . . . . .
H20 H 0.700998 -0.074551 0.902110 0.045 Uiso 1 1 calc R U . . .
C21 C 0.3811(10) 1.0351(8) 0.1380(5) 0.0363(11) Uani 1 1 d . . . . .
H21 H 0.408236 1.160874 0.138374 0.044 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 C4 1.899(5) . ?
S1 C12 1.800(5) . ?
S1 C13 1.753(6) . ?
N1 N2 1.313(7) . ?
N1 C14 1.369(7) . ?
N2 N3 1.342(7) . ?
N3 C13 1.373(7) . ?
N3 C19 1.456(8) . ?
C1 H1 0.9500 . ?
C1 C4 1.374(7) . ?
C1 C10 1.398(8) . ?
C2 H2 0.9500 . ?
C2 C8 1.383(8) . ?
C2 C20 1.399(9) . ?
C3 H3 0.9500 . ?
C3 C7 1.394(7) . ?
C3 C16 1.388(8) . ?
C4 C9 1.393(7) . ?
C5 H5 0.9500 . ?
C5 C9 1.382(8) . ?
C5 C12 1.396(7) . ?
C6 H6 0.9500 . ?
C6 C16 1.390(9) . ?
C6 C21 1.390(9) . ?
C7 C14 1.471(7) . ?
C7 C15 1.407(7) . ?
C8 H8 0.9500 . ?
C8 C18 1.389(8) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C12 1.384(7) . ?
C11 H11 0.9500 . ?
C11 C17 1.375(8) . ?
C11 C18 1.393(7) . ?
C13 C14 1.387(7) . ?
C15 H15 0.9500 . ?
C15 C21 1.389(8) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C20 1.390(9) . ?
C18 C19 1.512(9) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20 0.9500 . ?
C21 H21 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
C13 S1 C12 100.9(2) . . ?
N2 N1 C14 109.8(4) . . ?
N1 N2 N3 107.5(4) . . ?
N2 N3 C13 110.8(4) . . ?
N2 N3 C19 119.0(5) . . ?
C13 N3 C19 129.8(5) . . ?
C4 C1 H1 120.7 . . ?
C4 C1 C10 118.6(5) . . ?
C10 C1 H1 120.7 . . ?
C8 C2 H2 120.1 . . ?
C8 C2 C20 119.8(5) . . ?
C20 C2 H2 120.1 . . ?
C7 C3 H3 119.3 . . ?
C16 C3 H3 119.3 . . ?
C16 C3 C7 121.4(5) . . ?
C1 C4 Br1 120.0(4) . . ?
C1 C4 C9 121.6(5) . . ?
C9 C4 Br1 118.3(4) . . ?
C9 C5 H5 120.3 . . ?
C9 C5 C12 119.4(5) . . ?
C12 C5 H5 120.3 . . ?
C16 C6 H6 120.1 . . ?
C21 C6 H6 120.1 . . ?
C21 C6 C16 119.7(5) . . ?
C3 C7 C14 119.3(5) . . ?
C3 C7 C15 118.3(5) . . ?
C15 C7 C14 122.3(5) . . ?
C2 C8 H8 119.5 . . ?
C2 C8 C18 121.0(5) . . ?
C18 C8 H8 119.5 . . ?
C4 C9 H9 120.2 . . ?
C5 C9 C4 119.6(5) . . ?
C5 C9 H9 120.2 . . ?
C1 C10 H10 119.9 . . ?
C12 C10 C1 120.3(5) . . ?
C12 C10 H10 119.9 . . ?
C17 C11 H11 119.3 . . ?
C17 C11 C18 121.5(5) . . ?
C18 C11 H11 119.3 . . ?
C5 C12 S1 118.9(4) . . ?
C10 C12 S1 120.6(4) . . ?
C10 C12 C5 120.4(5) . . ?
N3 C13 S1 122.1(4) . . ?
N3 C13 C14 104.3(4) . . ?
C14 C13 S1 133.6(4) . . ?
N1 C14 C7 120.0(5) . . ?
N1 C14 C13 107.6(4) . . ?
C13 C14 C7 132.4(5) . . ?
C7 C15 H15 119.9 . . ?
C21 C15 C7 120.2(5) . . ?
C21 C15 H15 119.9 . . ?
C3 C16 C6 119.7(5) . . ?
C3 C16 H16 120.2 . . ?
C6 C16 H16 120.2 . . ?
C11 C17 H17 120.1 . . ?
C11 C17 C20 119.8(5) . . ?
C20 C17 H17 120.1 . . ?
C8 C18 C11 118.3(5) . . ?
C8 C18 C19 120.1(5) . . ?
C11 C18 C19 121.5(5) . . ?
N3 C19 C18 113.6(5) . . ?
N3 C19 H19A 108.8 . . ?
N3 C19 H19B 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C2 C20 H20 120.3 . . ?
C17 C20 C2 119.5(5) . . ?
C17 C20 H20 120.3 . . ?
C6 C21 H21 119.7 . . ?
C15 C21 C6 120.6(5) . . ?
C15 C21 H21 119.7 . . ?

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 C4 C9 C5 179.1(4) . . . . ?
S1 C13 C14 N1 -178.9(4) . . . . ?
S1 C13 C14 C7 2.6(8) . . . . ?
N1 N2 N3 C13 -1.0(5) . . . . ?
N1 N2 N3 C19 -175.1(5) . . . . ?
N2 N1 C14 C7 176.3(4) . . . . ?
N2 N1 C14 C13 -2.4(5) . . . . ?
N2 N3 C13 S1 -179.9(3) . . . . ?
N2 N3 C13 C14 -0.5(5) . . . . ?
N2 N3 C19 C18 -105.6(6) . . . . ?
N3 C13 C14 N1 1.7(5) . . . . ?
N3 C13 C14 C7 -176.8(5) . . . . ?
C1 C4 C9 C5 -0.9(8) . . . . ?
C1 C10 C12 S1 -176.4(4) . . . . ?
C1 C10 C12 C5 -0.5(8) . . . . ?
C2 C8 C18 C11 -1.2(8) . . . . ?
C2 C8 C18 C19 -179.1(5) . . . . ?
C3 C7 C14 N1 17.3(7) . . . . ?
C3 C7 C14 C13 -164.4(5) . . . . ?
C3 C7 C15 C21 1.3(7) . . . . ?
C4 C1 C10 C12 -0.5(8) . . . . ?
C7 C3 C16 C6 -0.6(8) . . . . ?
C7 C15 C21 C6 1.2(8) . . . . ?
C8 C2 C20 C17 1.1(8) . . . . ?
C8 C18 C19 N3 -140.8(6) . . . . ?
C9 C5 C12 S1 176.8(4) . . . . ?
C9 C5 C12 C10 0.8(8) . . . . ?
C10 C1 C4 Br1 -178.8(4) . . . . ?
C10 C1 C4 C9 1.2(8) . . . . ?
C11 C17 C20 C2 -1.2(8) . . . . ?
C11 C18 C19 N3 41.3(8) . . . . ?
C12 S1 C13 N3 -97.5(4) . . . . ?
C12 S1 C13 C14 83.2(5) . . . . ?
C12 C5 C9 C4 -0.1(8) . . . . ?
C13 S1 C12 C5 101.9(5) . . . . ?
C13 S1 C12 C10 -82.1(5) . . . . ?
C13 N3 C19 C18 81.6(7) . . . . ?
C14 N1 N2 N3 2.1(5) . . . . ?
C14 C7 C15 C21 180.0(5) . . . . ?
C15 C7 C14 N1 -161.3(4) . . . . ?
C15 C7 C14 C13 17.0(8) . . . . ?
C16 C3 C7 C14 179.7(5) . . . . ?
C16 C3 C7 C15 -1.6(7) . . . . ?
C16 C6 C21 C15 -3.5(9) . . . . ?
C17 C11 C18 C8 1.0(7) . . . . ?
C17 C11 C18 C19 179.0(5) . . . . ?
C18 C11 C17 C20 0.2(8) . . . . ?
C19 N3 C13 S1 -6.6(7) . . . . ?
C19 N3 C13 C14 172.8(5) . . . . ?
C20 C2 C8 C18 0.1(8) . . . . ?
C21 C6 C16 C3 3.2(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
