# 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_exp_2092_auto
_database_code_depnum_ccdc_archive 'CCDC 2143418'
loop_
_audit_author_name
_audit_author_address
'Yong-Yuan Gui'
;Sichuan Normal University
China
;
_audit_update_record             
;
2022-01-20 deposited with the CCDC.	2022-12-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Br N2 O'
_chemical_formula_weight         432.33

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   5.74860(10)
_cell_length_b                   8.1330(2)
_cell_length_c                   22.8334(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.015(2)
_cell_angle_gamma                90
_cell_volume                     1064.92(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(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    1.348
_exptl_crystal_F_000             442
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.746
_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      296(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            13925
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.940
_diffrn_reflns_theta_max         76.895
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4161
_reflns_number_gt                3587
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_max     0.876
_reflns_Friedel_fraction_full    0.951

_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0916P)²+0.2112P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0015(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1392 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4161
_refine_ls_number_parameters     256
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1543
_refine_ls_wR_factor_gt          0.1474
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002

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
Br28 Br 0.61183(15) 0.84612(15) 1.09767(3) 0.1133(4) Uani 1 1 d . . . . .
O17 O 1.0282(7) 0.7156(6) 0.82790(18) 0.0835(11) Uani 1 1 d . . . . .
N15 N 0.6435(9) 0.7041(6) 0.80117(19) 0.0716(11) Uani 1 1 d . . . . .
H15 H 0.5055 0.7069 0.8134 0.086 Uiso 1 1 calc R U . . .
C1 C 0.7237(6) 0.4940(5) 0.53048(17) 0.0463(8) Uani 1 1 d . . . . .
C3 C 0.7987(7) 0.3992(5) 0.63094(19) 0.0548(10) Uani 1 1 d . . . . .
H3 H 0.8834 0.3312 0.6573 0.066 Uiso 1 1 calc R U . . .
C16 C 0.8257(10) 0.7227(6) 0.8405(2) 0.0654(12) Uani 1 1 d . . . . .
C2 C 0.8450(7) 0.3961(6) 0.57189(19) 0.0563(10) Uani 1 1 d . . . . .
H2 H 0.9608 0.3264 0.5599 0.068 Uiso 1 1 calc R U . . .
C7 C 0.7731(7) 0.4920(5) 0.46755(18) 0.0493(8) Uani 1 1 d . . . . .
C22 C 0.7676(10) 0.7532(6) 0.9027(2) 0.0636(11) Uani 1 1 d . . . . .
C6 C 0.5513(9) 0.5948(7) 0.5510(2) 0.0701(13) Uani 1 1 d . . . . .
H6 H 0.4638 0.6610 0.5245 0.084 Uiso 1 1 calc R U . . .
C13 C 0.5823(7) 0.5100(6) 0.7164(2) 0.0567(10) Uani 1 1 d . . . . .
C4 C 0.6296(7) 0.5012(6) 0.65107(19) 0.0527(9) Uani 1 1 d . . . . .
C5 C 0.5069(9) 0.5991(8) 0.6096(2) 0.0717(14) Uani 1 1 d . . . . .
H5 H 0.3920 0.6694 0.6217 0.086 Uiso 1 1 calc R U . . .
C25 C 0.6822(10) 0.8093(7) 1.0187(2) 0.0724(14) Uani 1 1 d . . . . .
C23 C 0.5629(10) 0.8306(9) 0.9173(2) 0.0781(14) Uani 1 1 d . . . . .
H23 H 0.4532 0.8630 0.8876 0.094 Uiso 1 1 calc R U . . .
C12 C 0.6217(10) 0.5619(8) 0.4246(2) 0.0718(13) Uani 1 1 d . . . . .
H12 H 0.4862 0.6122 0.4356 0.086 Uiso 1 1 calc R U . . .
C24 C 0.5217(11) 0.8594(9) 0.9746(2) 0.0812(14) Uani 1 1 d . . . . .
H24 H 0.3858 0.9126 0.9838 0.097 Uiso 1 1 calc R U . . .
C18 C 0.7241(11) 0.3838(8) 0.7515(2) 0.0764(14) Uani 1 1 d . . . . .
H18 H 0.8822 0.4085 0.7565 0.092 Uiso 1 1 calc R U . . .
C8 C 0.9736(9) 0.4201(7) 0.4484(2) 0.0693(13) Uani 1 1 d . . . . .
H8 H 1.0814 0.3733 0.4758 0.083 Uiso 1 1 calc R U . . .
C10 C 0.8620(10) 0.4862(8) 0.3483(2) 0.0777(15) Uani 1 1 d . . . . .
H10 H 0.8907 0.4836 0.3088 0.093 Uiso 1 1 calc R U . . .
C14 C 0.6677(11) 0.6793(7) 0.7385(2) 0.0748(14) Uani 1 1 d . . . . .
H14A H 0.8304 0.6918 0.7308 0.090 Uiso 1 1 calc R U . . .
H14B H 0.5800 0.7639 0.7167 0.090 Uiso 1 1 calc R U . . .
C11 C 0.6657(12) 0.5590(8) 0.3659(3) 0.0830(16) Uani 1 1 d . . . . .
H11 H 0.5605 0.6072 0.3383 0.100 Uiso 1 1 calc R U . . .
C9 C 1.0166(11) 0.4167(9) 0.3893(3) 0.0843(18) Uani 1 1 d . . . . .
H9 H 1.1513 0.3669 0.3775 0.101 Uiso 1 1 calc R U . . .
C26 C 0.8816(12) 0.7330(10) 1.0063(3) 0.0885(18) Uani 1 1 d . . . . .
H26 H 0.9874 0.6985 1.0365 0.106 Uiso 1 1 calc R U . . .
C27 C 0.9274(10) 0.7064(9) 0.9480(3) 0.0785(15) Uani 1 1 d . . . . .
H27 H 1.0667 0.6569 0.9393 0.094 Uiso 1 1 calc R U . . .
C19 C 0.6698(16) 0.2531(10) 0.7750(3) 0.0959(19) Uani 1 1 d . . . . .
H19 H 0.5128 0.2244 0.7716 0.115 Uiso 1 1 calc R U . . .
C21 C 0.3229(9) 0.4880(13) 0.7228(3) 0.098(2) Uani 1 1 d . . . . .
H21A H 0.2398 0.5811 0.7061 0.148 Uiso 1 1 calc R U . . .
H21B H 0.2951 0.4792 0.7637 0.148 Uiso 1 1 calc R U . . .
H21C H 0.2698 0.3898 0.7027 0.148 Uiso 1 1 calc R U . . .
N20 N 0.832(2) 0.1370(10) 0.8085(4) 0.153(4) Uani 1 1 d . . . . .
H20A H 0.8393 0.0430 0.7887 0.184 Uiso 1 1 calc R U . . .
H20B H 0.7797 0.1175 0.8436 0.184 Uiso 1 1 calc R U . . .
H20C H 0.9736 0.1816 0.8129 0.184 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
Br28 C25 1.899(5) . ?
O17 C16 1.220(7) . ?
N15 C16 1.340(8) . ?
N15 C14 1.460(6) . ?
N15 H15 0.8600 . ?
C1 C2 1.386(6) . ?
C1 C6 1.393(6) . ?
C1 C7 1.484(5) . ?
C3 C4 1.381(6) . ?
C3 C2 1.393(6) . ?
C3 H3 0.9300 . ?
C16 C22 1.502(7) . ?
C2 H2 0.9300 . ?
C7 C12 1.387(7) . ?
C7 C8 1.390(6) . ?
C22 C27 1.388(8) . ?
C22 C23 1.395(8) . ?
C6 C5 1.380(7) . ?
C6 H6 0.9300 . ?
C13 C18 1.507(8) . ?
C13 C21 1.519(6) . ?
C13 C4 1.536(6) . ?
C13 C14 1.535(7) . ?
C4 C5 1.391(7) . ?
C5 H5 0.9300 . ?
C25 C26 1.351(10) . ?
C25 C24 1.379(9) . ?
C23 C24 1.367(7) . ?
C23 H23 0.9300 . ?
C12 C11 1.380(8) . ?
C12 H12 0.9300 . ?
C24 H24 0.9300 . ?
C18 C19 1.240(10) . ?
C18 H18 0.9300 . ?
C8 C9 1.391(8) . ?
C8 H8 0.9300 . ?
C10 C11 1.359(9) . ?
C10 C9 1.366(9) . ?
C10 H10 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C11 H11 0.9300 . ?
C9 H9 0.9300 . ?
C26 C27 1.392(9) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C19 N20 1.498(12) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N20 H20A 0.8900 . ?
N20 H20B 0.8900 . ?
N20 H20C 0.8900 . ?

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
C16 N15 C14 123.3(5) . . ?
C16 N15 H15 118.4 . . ?
C14 N15 H15 118.4 . . ?
C2 C1 C6 116.4(4) . . ?
C2 C1 C7 122.2(3) . . ?
C6 C1 C7 121.4(4) . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
O17 C16 N15 123.4(5) . . ?
O17 C16 C22 120.7(5) . . ?
N15 C16 C22 115.9(5) . . ?
C1 C2 C3 121.9(4) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C12 C7 C8 116.3(4) . . ?
C12 C7 C1 121.9(4) . . ?
C8 C7 C1 121.9(4) . . ?
C27 C22 C23 118.1(5) . . ?
C27 C22 C16 118.7(5) . . ?
C23 C22 C16 123.2(5) . . ?
C5 C6 C1 121.7(4) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C18 C13 C21 111.5(5) . . ?
C18 C13 C4 111.0(4) . . ?
C21 C13 C4 109.2(4) . . ?
C18 C13 C14 106.7(4) . . ?
C21 C13 C14 111.5(5) . . ?
C4 C13 C14 106.7(4) . . ?
C3 C4 C5 116.9(4) . . ?
C3 C4 C13 121.9(4) . . ?
C5 C4 C13 121.2(4) . . ?
C6 C5 C4 121.8(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C26 C25 C24 121.1(5) . . ?
C26 C25 Br28 120.8(4) . . ?
C24 C25 Br28 118.1(4) . . ?
C24 C23 C22 120.8(5) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C11 C12 C7 122.1(5) . . ?
C11 C12 H12 119.0 . . ?
C7 C12 H12 119.0 . . ?
C23 C24 C25 119.8(5) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C19 C18 C13 132.1(7) . . ?
C19 C18 H18 113.9 . . ?
C13 C18 H18 113.9 . . ?
C7 C8 C9 121.4(5) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C11 C10 C9 119.5(5) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
N15 C14 C13 113.3(4) . . ?
N15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
N15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C10 C11 C12 120.4(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C10 C9 C8 120.3(5) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C25 C26 C27 119.5(6) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C22 C27 C26 120.7(6) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C18 C19 N20 126.4(9) . . ?
C18 C19 H19 116.8 . . ?
N20 C19 H19 116.8 . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 N20 H20A 109.5 . . ?
C19 N20 H20B 109.5 . . ?
H20A N20 H20B 109.5 . . ?
C19 N20 H20C 109.5 . . ?
H20A N20 H20C 109.5 . . ?
H20B N20 H20C 109.5 . . ?

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
C14 N15 C16 O17 -2.3(8) . . . . ?
C14 N15 C16 C22 177.8(5) . . . . ?
C6 C1 C2 C3 -0.5(7) . . . . ?
C7 C1 C2 C3 179.6(4) . . . . ?
C4 C3 C2 C1 -0.4(7) . . . . ?
C2 C1 C7 C12 166.0(5) . . . . ?
C6 C1 C7 C12 -13.9(7) . . . . ?
C2 C1 C7 C8 -14.0(6) . . . . ?
C6 C1 C7 C8 166.1(5) . . . . ?
O17 C16 C22 C27 -26.6(8) . . . . ?
N15 C16 C22 C27 153.3(5) . . . . ?
O17 C16 C22 C23 151.6(6) . . . . ?
N15 C16 C22 C23 -28.6(8) . . . . ?
C2 C1 C6 C5 1.2(8) . . . . ?
C7 C1 C6 C5 -179.0(5) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
C2 C3 C4 C13 -177.9(4) . . . . ?
C18 C13 C4 C3 -5.8(6) . . . . ?
C21 C13 C4 C3 -129.1(6) . . . . ?
C14 C13 C4 C3 110.2(5) . . . . ?
C18 C13 C4 C5 175.8(5) . . . . ?
C21 C13 C4 C5 52.5(7) . . . . ?
C14 C13 C4 C5 -68.3(6) . . . . ?
C1 C6 C5 C4 -1.0(9) . . . . ?
C3 C4 C5 C6 0.1(8) . . . . ?
C13 C4 C5 C6 178.6(5) . . . . ?
C27 C22 C23 C24 0.0(10) . . . . ?
C16 C22 C23 C24 -178.2(6) . . . . ?
C8 C7 C12 C11 0.6(9) . . . . ?
C1 C7 C12 C11 -179.4(5) . . . . ?
C22 C23 C24 C25 -1.0(11) . . . . ?
C26 C25 C24 C23 0.5(10) . . . . ?
Br28 C25 C24 C23 -178.0(6) . . . . ?
C21 C13 C18 C19 14.7(9) . . . . ?
C4 C13 C18 C19 -107.3(7) . . . . ?
C14 C13 C18 C19 136.8(7) . . . . ?
C12 C7 C8 C9 -1.0(8) . . . . ?
C1 C7 C8 C9 179.0(5) . . . . ?
C16 N15 C14 C13 114.8(6) . . . . ?
C18 C13 C14 N15 -58.8(6) . . . . ?
C21 C13 C14 N15 63.2(7) . . . . ?
C4 C13 C14 N15 -177.5(4) . . . . ?
C9 C10 C11 C12 -0.5(10) . . . . ?
C7 C12 C11 C10 0.1(10) . . . . ?
C11 C10 C9 C8 0.1(10) . . . . ?
C7 C8 C9 C10 0.7(10) . . . . ?
C24 C25 C26 C27 0.9(11) . . . . ?
Br28 C25 C26 C27 179.4(5) . . . . ?
C23 C22 C27 C26 1.4(10) . . . . ?
C16 C22 C27 C26 179.7(6) . . . . ?
C25 C26 C27 C22 -1.9(11) . . . . ?
C13 C18 C19 N20 179.1(7) . . . . ?

_refine_diff_density_max         0.632
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.053

