# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_mj24441_0m
_database_code_depnum_ccdc_archive 'CCDC 2356244'
loop_
_audit_author_name
_audit_author_address
CO
;SIOC
China
;
_audit_update_record             
;
2024-05-18 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
_audit_creation_date             2024-05-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 Br N O2'
_chemical_formula_sum            'C17 H14 Br N O2'
_chemical_formula_weight         344.20
_chemical_absolute_configuration rmad
_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 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   33.0990(7)
_cell_length_b                   5.83420(10)
_cell_length_c                   7.8722(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.5400(10)
_cell_angle_gamma                90
_cell_volume                     1519.62(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7048
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      54.911
_cell_measurement_theta_min      4.652
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.681
_exptl_absorpt_coefficient_mu    2.452
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1016 before and 0.0643 after correction.
The Ratio of minimum to maximum transmission is 0.7292.
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    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8082
_diffrn_reflns_point_group_measured_fraction_full 0.911
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.900
_diffrn_reflns_theta_min         4.651
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_full    0.811
_reflns_Friedel_fraction_max     0.787
_reflns_number_gt                2488
_reflns_number_total             2603
_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 1.5 (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  (Sheldrick, 2015)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 928 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0278
_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)+(0.0417P)²+0.3479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0804
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17)
2.d X=CH2 refined with riding coordinates:
 C3(H3A,H3B)
;
_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 0.47654(2) 0.63318(10) 0.73321(5) 0.0602(2) Uani 1 1 d . . . . .
O1 O 0.27576(6) 0.6132(5) 0.2521(2) 0.0309(5) Uani 1 1 d . . . . .
O2 O 0.27281(7) 0.8379(4) 0.4851(3) 0.0336(5) Uani 1 1 d . . . . .
N1 N 0.31127(7) 0.5108(4) 0.4839(3) 0.0204(5) Uani 1 1 d . . . . .
C1 C 0.31651(9) 0.3158(5) 0.3692(4) 0.0221(6) Uani 1 1 d . . . . .
H1 H 0.304163 0.175309 0.418787 0.027 Uiso 1 1 calc R U . . .
C2 C 0.29111(9) 0.3969(6) 0.2167(4) 0.0276(7) Uani 1 1 d . . . . .
C3 C 0.28312(11) 0.2898(8) 0.0739(4) 0.0436(9) Uani 1 1 d . . . . .
H3A H 0.266216 0.359638 -0.010722 0.052 Uiso 1 1 calc R U . . .
H3B H 0.294215 0.142210 0.054688 0.052 Uiso 1 1 calc R U . . .
C4 C 0.28574(8) 0.6691(5) 0.4192(4) 0.0236(6) Uani 1 1 d . . . . .
C5 C 0.31688(9) 0.4910(6) 0.6681(4) 0.0255(6) Uani 1 1 d . . . . .
H5A H 0.322115 0.328498 0.697558 0.031 Uiso 1 1 calc R U . . .
H5B H 0.291619 0.537639 0.723021 0.031 Uiso 1 1 calc R U . . .
C6 C 0.35155(8) 0.6369(6) 0.7382(3) 0.0244(6) Uani 1 1 d . . . . .
C7 C 0.39163(10) 0.5757(5) 0.7103(4) 0.0293(7) Uani 1 1 d . . . . .
H7 H 0.397816 0.440981 0.648387 0.035 Uiso 1 1 calc R U . . .
C8 C 0.42214(10) 0.7156(6) 0.7748(4) 0.0341(8) Uani 1 1 d . . . . .
C9 C 0.41449(11) 0.9116(7) 0.8667(4) 0.0393(8) Uani 1 1 d . . . . .
H9 H 0.436062 1.004213 0.909627 0.047 Uiso 1 1 calc R U . . .
C10 C 0.37453(12) 0.9708(7) 0.8950(5) 0.0401(8) Uani 1 1 d . . . . .
H10 H 0.368467 1.104534 0.958239 0.048 Uiso 1 1 calc R U . . .
C11 C 0.34342(10) 0.8324(6) 0.8301(4) 0.0330(7) Uani 1 1 d . . . . .
H11 H 0.316149 0.873394 0.849358 0.040 Uiso 1 1 calc R U . . .
C12 C 0.36047(9) 0.2707(5) 0.3311(4) 0.0222(6) Uani 1 1 d . . . . .
C13 C 0.37890(10) 0.0718(5) 0.3908(4) 0.0288(7) Uani 1 1 d . . . . .
H13 H 0.363685 -0.038058 0.451065 0.035 Uiso 1 1 calc R U . . .
C14 C 0.41979(11) 0.0330(6) 0.3623(5) 0.0371(8) Uani 1 1 d . . . . .
H14 H 0.432492 -0.102305 0.404466 0.045 Uiso 1 1 calc R U . . .
C15 C 0.44171(10) 0.1914(6) 0.2729(4) 0.0375(8) Uani 1 1 d . . . . .
H15 H 0.469510 0.164488 0.253378 0.045 Uiso 1 1 calc R U . . .
C16 C 0.42350(10) 0.3890(6) 0.2117(4) 0.0338(7) Uani 1 1 d . . . . .
H16 H 0.438689 0.497072 0.149598 0.041 Uiso 1 1 calc R U . . .
C17 C 0.38282(9) 0.4293(5) 0.2412(4) 0.0275(7) Uani 1 1 d . . . . .
H17 H 0.370311 0.565521 0.199828 0.033 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 C8 1.901(3) . ?
O1 C2 1.392(4) . ?
O1 C4 1.386(3) . ?
O2 C4 1.197(4) . ?
N1 C1 1.466(4) . ?
N1 C4 1.343(4) . ?
N1 C5 1.461(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.523(4) . ?
C1 C12 1.516(4) . ?
C2 C3 1.307(5) . ?
C3 H3A 0.9500 . ?
C3 H3B 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.521(4) . ?
C6 C7 1.397(4) . ?
C6 C11 1.381(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(5) . ?
C8 C9 1.380(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.395(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(4) . ?
C12 C17 1.390(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.396(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(5) . ?
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
C4 O1 C2 109.0(2) . . ?
C4 N1 C1 112.6(2) . . ?
C4 N1 C5 119.5(2) . . ?
C5 N1 C1 122.4(2) . . ?
N1 C1 H1 109.8 . . ?
N1 C1 C2 99.9(2) . . ?
N1 C1 C12 112.8(2) . . ?
C2 C1 H1 109.8 . . ?
C12 C1 H1 109.8 . . ?
C12 C1 C2 114.2(2) . . ?
O1 C2 C1 108.7(2) . . ?
C3 C2 O1 122.6(3) . . ?
C3 C2 C1 128.7(3) . . ?
C2 C3 H3A 120.0 . . ?
C2 C3 H3B 120.0 . . ?
H3A C3 H3B 120.0 . . ?
O2 C4 O1 121.7(3) . . ?
O2 C4 N1 129.0(3) . . ?
N1 C4 O1 109.2(2) . . ?
N1 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
N1 C5 C6 113.0(2) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C7 C6 C5 120.7(3) . . ?
C11 C6 C5 119.8(3) . . ?
C11 C6 C7 119.5(3) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 C6 118.6(3) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 Br1 118.2(3) . . ?
C9 C8 Br1 119.2(3) . . ?
C9 C8 C7 122.6(3) . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.6(3) . . ?
C10 C9 H9 120.7 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C6 C11 C10 121.2(3) . . ?
C6 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C1 119.6(3) . . ?
C13 C12 C17 119.6(3) . . ?
C17 C12 C1 120.8(3) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 120.2(3) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 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 C8 C9 C10 179.5(3) . . . . ?
N1 C1 C2 O1 1.3(3) . . . . ?
N1 C1 C2 C3 -177.6(3) . . . . ?
N1 C1 C12 C13 112.6(3) . . . . ?
N1 C1 C12 C17 -65.6(3) . . . . ?
N1 C5 C6 C7 -72.4(4) . . . . ?
N1 C5 C6 C11 107.4(3) . . . . ?
C1 N1 C4 O1 -7.4(3) . . . . ?
C1 N1 C4 O2 173.8(3) . . . . ?
C1 N1 C5 C6 116.6(3) . . . . ?
C1 C12 C13 C14 -177.4(3) . . . . ?
C1 C12 C17 C16 178.0(3) . . . . ?
C2 O1 C4 O2 -173.0(3) . . . . ?
C2 O1 C4 N1 8.1(3) . . . . ?
C2 C1 C12 C13 -134.2(3) . . . . ?
C2 C1 C12 C17 47.6(4) . . . . ?
C4 O1 C2 C1 -5.7(3) . . . . ?
C4 O1 C2 C3 173.3(3) . . . . ?
C4 N1 C1 C2 3.7(3) . . . . ?
C4 N1 C1 C12 125.4(3) . . . . ?
C4 N1 C5 C6 -91.5(3) . . . . ?
C5 N1 C1 C2 157.3(2) . . . . ?
C5 N1 C1 C12 -81.0(3) . . . . ?
C5 N1 C4 O1 -161.9(2) . . . . ?
C5 N1 C4 O2 19.4(5) . . . . ?
C5 C6 C7 C8 179.2(3) . . . . ?
C5 C6 C11 C10 -179.5(3) . . . . ?
C6 C7 C8 Br1 -179.1(2) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C7 C6 C11 C10 0.3(5) . . . . ?
C7 C8 C9 C10 -0.1(6) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C9 C10 C11 C6 0.2(6) . . . . ?
C11 C6 C7 C8 -0.6(5) . . . . ?
C12 C1 C2 O1 -119.3(3) . . . . ?
C12 C1 C2 C3 61.8(5) . . . . ?
C12 C13 C14 C15 -0.8(5) . . . . ?
C13 C12 C17 C16 -0.2(5) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C12 -0.4(5) . . . . ?
C17 C12 C13 C14 0.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
