# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_mo_241214d_wsg_fzw_4_br
_database_code_depnum_ccdc_archive 'CCDC 2410419'
loop_
_audit_author_name
_audit_author_address
'shi cao'
;Shenzhen University
China
;
_audit_update_record             
;
2024-12-16 deposited with the CCDC.	2026-02-06 downloaded from the CCDC.
;
_audit_creation_date             2024-12-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 Br N2 O2, C H2 Cl2'
_chemical_formula_sum            'C21 H15 Br Cl2 N2 O2'
_chemical_formula_weight         478.16
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.5877(4)
_cell_length_b                   13.8995(6)
_cell_length_c                   9.0520(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.623(2)
_cell_angle_gamma                90
_cell_volume                     1017.74(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9852
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.334
_cell_measurement_theta_min      2.803
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.597
_exptl_absorpt_coefficient_mu    2.301
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1190 before and 0.0834 after correction.
The Ratio of minimum to maximum transmission is 0.7831.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            42899
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.376
_diffrn_reflns_theta_min         2.518
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker Apex-III CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3561
_reflns_number_total             3667
_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 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 1644 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3667
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      1.054
_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)+(0.0230P)²+0.7434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0603
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C17(H17), C10(H10), C7(H7), C6(H6), C18(H18), C19(H19),
 C12(H12), C9(H9), C20(H20), C14(H14)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.03765(4) 0.27503(3) 0.63809(4) 0.02272(12) Uani 1 1 d . . . . .
Cl1 Cl 1.18349(19) 0.58476(13) 0.70035(19) 0.0621(4) Uani 1 1 d . . . . .
Cl2 Cl 1.0341(3) 0.72580(12) 0.8476(3) 0.0776(5) Uani 1 1 d . . . . .
N1 N 0.5226(4) 0.3926(2) 0.3528(3) 0.0125(6) Uani 1 1 d . . . . .
O2 O 0.3965(3) 0.2823(3) 0.4585(3) 0.0208(5) Uani 1 1 d . . . . .
O1 O 0.6200(3) 0.61224(18) 0.4338(3) 0.0182(5) Uani 1 1 d . . . . .
H1 H 0.6082 0.6698 0.4563 0.027 Uiso 1 1 calc R U . . .
C16 C 0.3596(4) 0.4301(2) 0.2663(4) 0.0145(7) Uani 1 1 d . . . . .
C4 C 0.6544(4) 0.4164(3) 0.0056(4) 0.0172(8) Uani 1 1 d . . . . .
H4 H 0.6613 0.3597 0.0660 0.021 Uiso 1 1 calc R U . . .
C3 C 0.6378(4) 0.5073(3) 0.0699(4) 0.0144(7) Uani 1 1 d . . . . .
C2 C 0.6373(4) 0.5175(3) 0.2269(4) 0.0132(7) Uani 1 1 d . . . . .
C5 C 0.6605(5) 0.4102(3) -0.1426(5) 0.0209(8) Uani 1 1 d . . . . .
H5 H 0.6735 0.3491 -0.1839 0.025 Uiso 1 1 calc R U . . .
N2 N 0.2989(4) 0.4019(2) 0.1182(4) 0.0183(7) Uani 1 1 d . . . . .
C11 C 0.6181(4) 0.6069(3) 0.2843(4) 0.0138(7) Uani 1 1 d . . . . .
C17 C 0.2830(5) 0.4901(3) 0.3417(5) 0.0176(8) Uani 1 1 d . . . . .
H17 H 0.3328 0.5061 0.4493 0.021 Uiso 1 1 calc R U . . .
C10 C 0.6001(5) 0.6898(3) 0.1895(5) 0.0167(8) Uani 1 1 d . . . . .
H10 H 0.5851 0.7510 0.2296 0.020 Uiso 1 1 calc R U . . .
C7 C 0.6293(5) 0.5817(3) -0.1772(4) 0.0189(8) Uani 1 1 d . . . . .
H7 H 0.6203 0.6375 -0.2403 0.023 Uiso 1 1 calc R U . . .
C6 C 0.6477(5) 0.4933(3) -0.2357(4) 0.0201(8) Uani 1 1 d . . . . .
H6 H 0.6519 0.4879 -0.3389 0.024 Uiso 1 1 calc R U . . .
C18 C 0.1288(5) 0.5261(3) 0.2522(5) 0.0212(8) Uani 1 1 d . . . . .
H18 H 0.0702 0.5682 0.2975 0.025 Uiso 1 1 calc R U . . .
C19 C 0.0624(5) 0.4995(3) 0.0965(5) 0.0237(9) Uani 1 1 d . . . . .
H19 H -0.0421 0.5236 0.0327 0.028 Uiso 1 1 calc R U . . .
C12 C 0.8135(5) 0.3981(3) 0.4148(4) 0.0158(7) Uani 1 1 d . . . . .
H12 H 0.9103 0.4253 0.4033 0.019 Uiso 1 1 calc R U . . .
C9 C 0.6042(4) 0.6823(3) 0.0400(5) 0.0170(8) Uani 1 1 d . . . . .
H9 H 0.5941 0.7385 -0.0223 0.020 Uiso 1 1 calc R U . . .
C20 C 0.1500(5) 0.4376(3) 0.0353(5) 0.0233(9) Uani 1 1 d . . . . .
H20 H 0.1024 0.4191 -0.0715 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8242(5) 0.3197(3) 0.5175(4) 0.0179(8) Uani 1 1 d . . . . .
C1 C 0.6616(4) 0.4333(2) 0.3331(4) 0.0134(7) Uani 1 1 d . . . . .
C15 C 0.5285(5) 0.3142(3) 0.4501(4) 0.0148(7) Uani 1 1 d . . . . .
C14 C 0.6894(4) 0.2780(4) 0.5341(4) 0.0169(6) Uani 1 1 d . . . . .
H14 H 0.7016 0.2242 0.6020 0.020 Uiso 1 1 calc R U . . .
C8 C 0.6235(4) 0.5909(3) -0.0230(4) 0.0153(7) Uani 1 1 d . . . . .
C21 C 0.9992(6) 0.6292(5) 0.7217(6) 0.0465(14) Uani 1 1 d . . . . .
H21A H 0.9224 0.6488 0.6177 0.056 Uiso 1 1 calc R U . . .
H21B H 0.9456 0.5771 0.7618 0.056 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 C13 1.896(4) . ?
Cl1 C21 1.769(6) . ?
Cl2 C21 1.721(7) . ?
N1 C16 1.452(5) . ?
N1 C1 1.386(5) . ?
N1 C15 1.391(5) . ?
O2 C15 1.243(5) . ?
O1 H1 0.8400 . ?
O1 C11 1.351(4) . ?
C16 N2 1.324(5) . ?
C16 C17 1.376(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.418(5) . ?
C4 C5 1.363(5) . ?
C3 C2 1.430(5) . ?
C3 C8 1.415(5) . ?
C2 C11 1.378(5) . ?
C2 C1 1.484(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.412(6) . ?
N2 C20 1.342(5) . ?
C11 C10 1.414(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(6) . ?
C10 H10 0.9500 . ?
C10 C9 1.369(6) . ?
C7 H7 0.9500 . ?
C7 C6 1.368(6) . ?
C7 C8 1.419(5) . ?
C6 H6 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.381(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.376(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.416(5) . ?
C12 C1 1.357(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.425(5) . ?
C20 H20 0.9500 . ?
C13 C14 1.347(6) . ?
C15 C14 1.426(5) . ?
C14 H14 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?

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
C1 N1 C16 120.0(3) . . ?
C1 N1 C15 123.5(3) . . ?
C15 N1 C16 116.6(3) . . ?
C11 O1 H1 109.5 . . ?
N2 C16 N1 114.8(3) . . ?
N2 C16 C17 126.2(4) . . ?
C17 C16 N1 119.0(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.2(4) . . ?
C4 C3 C2 122.1(3) . . ?
C8 C3 C4 119.2(3) . . ?
C8 C3 C2 118.7(3) . . ?
C3 C2 C1 121.2(3) . . ?
C11 C2 C3 120.3(3) . . ?
C11 C2 C1 118.5(3) . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C16 N2 C20 115.7(3) . . ?
O1 C11 C2 117.7(3) . . ?
O1 C11 C10 121.7(3) . . ?
C2 C11 C10 120.6(3) . . ?
C16 C17 H17 121.7 . . ?
C16 C17 C18 116.7(4) . . ?
C18 C17 H17 121.7 . . ?
C11 C10 H10 119.9 . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.5(4) . . ?
C8 C7 H7 119.7 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(4) . . ?
C7 C6 H6 120.0 . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.9(4) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 118.9(4) . . ?
C20 C19 H19 120.5 . . ?
C13 C12 H12 120.9 . . ?
C1 C12 H12 120.9 . . ?
C1 C12 C13 118.3(3) . . ?
C10 C9 H9 119.7 . . ?
C10 C9 C8 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
N2 C20 C19 123.6(4) . . ?
N2 C20 H20 118.2 . . ?
C19 C20 H20 118.2 . . ?
C12 C13 Br1 117.8(3) . . ?
C14 C13 Br1 119.7(3) . . ?
C14 C13 C12 122.4(4) . . ?
N1 C1 C2 117.7(3) . . ?
C12 C1 N1 119.7(3) . . ?
C12 C1 C2 122.5(3) . . ?
N1 C15 C14 115.9(3) . . ?
O2 C15 N1 118.5(3) . . ?
O2 C15 C14 125.6(3) . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C3 C8 C7 119.1(3) . . ?
C3 C8 C9 119.6(3) . . ?
C7 C8 C9 121.4(3) . . ?
Cl1 C21 H21A 109.1 . . ?
Cl1 C21 H21B 109.1 . . ?
Cl2 C21 Cl1 112.5(3) . . ?
Cl2 C21 H21A 109.1 . . ?
Cl2 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?

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 C13 C14 C15 176.7(3) . . . . ?
N1 C16 N2 C20 -178.6(3) . . . . ?
N1 C16 C17 C18 178.4(3) . . . . ?
N1 C15 C14 C13 0.4(5) . . . . ?
O2 C15 C14 C13 -178.8(4) . . . . ?
O1 C11 C10 C9 177.8(3) . . . . ?
C16 N1 C1 C2 2.4(5) . . . . ?
C16 N1 C1 C12 179.7(3) . . . . ?
C16 N1 C15 O2 -0.9(5) . . . . ?
C16 N1 C15 C14 179.9(3) . . . . ?
C16 N2 C20 C19 -0.1(6) . . . . ?
C16 C17 C18 C19 0.5(5) . . . . ?
C4 C3 C2 C11 -178.9(3) . . . . ?
C4 C3 C2 C1 2.7(5) . . . . ?
C4 C3 C8 C7 -1.2(5) . . . . ?
C4 C3 C8 C9 179.0(3) . . . . ?
C4 C5 C6 C7 0.1(6) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C3 C2 C11 O1 -179.4(3) . . . . ?
C3 C2 C11 C10 -0.5(5) . . . . ?
C3 C2 C1 N1 -100.4(4) . . . . ?
C3 C2 C1 C12 82.3(5) . . . . ?
C2 C3 C8 C7 178.0(3) . . . . ?
C2 C3 C8 C9 -1.8(5) . . . . ?
C2 C11 C10 C9 -1.1(5) . . . . ?
C5 C4 C3 C2 -177.6(3) . . . . ?
C5 C4 C3 C8 1.6(5) . . . . ?
N2 C16 C17 C18 -1.6(6) . . . . ?
C11 C2 C1 N1 81.2(4) . . . . ?
C11 C2 C1 C12 -96.0(4) . . . . ?
C11 C10 C9 C8 1.2(5) . . . . ?
C17 C16 N2 C20 1.4(5) . . . . ?
C17 C18 C19 C20 0.7(6) . . . . ?
C10 C9 C8 C3 0.3(5) . . . . ?
C10 C9 C8 C7 -179.5(3) . . . . ?
C6 C7 C8 C3 0.3(5) . . . . ?
C6 C7 C8 C9 -179.9(4) . . . . ?
C18 C19 C20 N2 -0.9(6) . . . . ?
C12 C13 C14 C15 -1.9(6) . . . . ?
C13 C12 C1 N1 0.4(5) . . . . ?
C13 C12 C1 C2 177.6(3) . . . . ?
C1 N1 C16 N2 78.5(4) . . . . ?
C1 N1 C16 C17 -101.5(4) . . . . ?
C1 N1 C15 O2 -179.2(3) . . . . ?
C1 N1 C15 C14 1.5(5) . . . . ?
C1 C2 C11 O1 -1.1(5) . . . . ?
C1 C2 C11 C10 177.9(3) . . . . ?
C1 C12 C13 Br1 -177.2(3) . . . . ?
C1 C12 C13 C14 1.5(6) . . . . ?
C15 N1 C16 N2 -99.9(4) . . . . ?
C15 N1 C16 C17 80.1(4) . . . . ?
C15 N1 C1 C2 -179.3(3) . . . . ?
C15 N1 C1 C12 -2.0(5) . . . . ?
C8 C3 C2 C11 1.9(5) . . . . ?
C8 C3 C2 C1 -176.4(3) . . . . ?
C8 C7 C6 C5 0.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
