# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 2257614'
loop_
_audit_author_name
_audit_author_address
'Ruchun Yang'
;Jiangxi Science and Technology Normal University
China
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2023-05-12 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            'C18 H17 Br2 N O2'
_chemical_formula_weight         439.15

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.4782(13)
_cell_length_b                   14.044(2)
_cell_length_c                   14.818(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1764.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3016
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      22.37

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    4.603
_shelx_estimated_absorpt_T_min   0.381
_shelx_estimated_absorpt_T_max   0.431
_exptl_absorpt_correction_type   none
_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     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9012
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.768
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3085
_reflns_number_gt                2597
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0337P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 956 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.005(7)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         3085
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0629
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   0.919
_refine_ls_restrained_S_all      0.919
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br2 Br 0.90941(6) 0.42484(4) 0.65484(4) 0.05161(18) Uani 1 1 d . . . . .
Br1 Br 0.70836(7) 0.38215(4) 0.82980(4) 0.05597(19) Uani 1 1 d . . . . .
O1 O 0.6553(3) 0.5839(2) 0.62592(19) 0.0321(7) Uani 1 1 d . . . . .
O2 O 0.5138(4) 0.5512(2) 0.7565(2) 0.0380(8) Uani 1 1 d . . . . .
N1 N 0.8352(5) 0.6483(3) 0.7308(3) 0.0397(11) Uani 1 1 d . . . . .
C16 C 0.5588(5) 0.4181(3) 0.5434(3) 0.0329(11) Uani 1 1 d . . . . .
H16 H 0.6364 0.4538 0.5148 0.039 Uiso 1 1 calc R U . . .
C10 C 0.6061(6) 0.5112(3) 0.6881(3) 0.0313(11) Uani 1 1 d . . . . .
C6 C 0.7447(5) 0.7423(3) 0.6053(3) 0.0304(11) Uani 1 1 d . . . . .
C7 C 0.7519(5) 0.6540(3) 0.6604(3) 0.0314(10) Uani 1 1 d . . . . .
C11 C 0.5217(5) 0.4359(3) 0.6332(3) 0.0283(10) Uani 1 1 d . . . . .
C15 C 0.4805(6) 0.3475(3) 0.4966(3) 0.0379(12) Uani 1 1 d . . . . .
H15 H 0.5080 0.3350 0.4370 0.045 Uiso 1 1 calc R U . . .
C3 C 0.7291(6) 0.9119(4) 0.5105(3) 0.0459(13) Uani 1 1 d . . . . .
H3 H 0.7224 0.9693 0.4794 0.055 Uiso 1 1 calc R U . . .
C9 C 0.7564(6) 0.4777(3) 0.7395(3) 0.0361(12) Uani 1 1 d . . . . .
C14 C 0.3640(7) 0.2960(4) 0.5363(3) 0.0457(14) Uani 1 1 d . . . . .
H14 H 0.3108 0.2494 0.5038 0.055 Uiso 1 1 calc R U . . .
C12 C 0.4036(6) 0.3821(4) 0.6739(3) 0.0419(12) Uani 1 1 d . . . . .
H12 H 0.3779 0.3927 0.7341 0.050 Uiso 1 1 calc R U . . .
C5 C 0.8424(6) 0.8179(4) 0.6277(3) 0.0389(12) Uani 1 1 d . . . . .
H5 H 0.9140 0.8117 0.6748 0.047 Uiso 1 1 calc R U . . .
C4 C 0.8339(6) 0.9020(3) 0.5804(4) 0.0463(14) Uani 1 1 d . . . . .
H4 H 0.8995 0.9525 0.5959 0.056 Uiso 1 1 calc R U . . .
C8 C 0.8285(6) 0.5635(4) 0.7859(3) 0.0444(13) Uani 1 1 d . . . . .
H8A H 0.7679 0.5774 0.8398 0.053 Uiso 1 1 calc R U . . .
H8B H 0.9348 0.5473 0.8047 0.053 Uiso 1 1 calc R U . . .
C1 C 0.6417(6) 0.7524(4) 0.5342(3) 0.0446(14) Uani 1 1 d . . . . .
H1 H 0.5765 0.7019 0.5181 0.053 Uiso 1 1 calc R U . . .
C13 C 0.3248(7) 0.3134(4) 0.6257(4) 0.0473(14) Uani 1 1 d . . . . .
H13 H 0.2449 0.2784 0.6531 0.057 Uiso 1 1 calc R U . . .
C2 C 0.6342(7) 0.8369(4) 0.4865(4) 0.0561(17) Uani 1 1 d . . . . .
H2 H 0.5649 0.8429 0.4382 0.067 Uiso 1 1 calc R U . . .
C17 C 0.3793(7) 0.6062(4) 0.7276(4) 0.0584(16) Uani 1 1 d . . . . .
H17A H 0.3061 0.5660 0.6948 0.070 Uiso 1 1 calc R U . . .
H17B H 0.4130 0.6574 0.6881 0.070 Uiso 1 1 calc R U . . .
C18 C 0.3018(8) 0.6458(4) 0.8085(4) 0.073(2) Uani 1 1 d . . . . .
H18A H 0.2119 0.6828 0.7907 0.110 Uiso 1 1 calc R U . . .
H18B H 0.3749 0.6857 0.8405 0.110 Uiso 1 1 calc R U . . .
H18C H 0.2683 0.5948 0.8471 0.110 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
Br2 C9 1.951(5) . ?
Br1 C9 1.938(5) . ?
O1 C7 1.379(5) . ?
O1 C10 1.438(5) . ?
O2 C10 1.398(5) . ?
O2 C17 1.443(6) . ?
N1 C7 1.262(6) . ?
N1 C8 1.444(6) . ?
C16 C15 1.380(6) . ?
C16 C11 1.391(6) . ?
C16 H16 0.9300 . ?
C10 C11 1.513(6) . ?
C10 C9 1.557(7) . ?
C6 C1 1.376(6) . ?
C6 C5 1.387(7) . ?
C6 C7 1.486(6) . ?
C11 C12 1.391(6) . ?
C15 C14 1.359(7) . ?
C15 H15 0.9300 . ?
C3 C4 1.372(7) . ?
C3 C2 1.372(7) . ?
C3 H3 0.9300 . ?
C9 C8 1.516(7) . ?
C14 C13 1.387(7) . ?
C14 H14 0.9300 . ?
C12 C13 1.374(7) . ?
C12 H12 0.9300 . ?
C5 C4 1.375(7) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C2 1.383(7) . ?
C1 H1 0.9300 . ?
C13 H13 0.9300 . ?
C2 H2 0.9300 . ?
C17 C18 1.476(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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 O1 C10 116.2(3) . . ?
C10 O2 C17 116.3(4) . . ?
C7 N1 C8 119.8(4) . . ?
C15 C16 C11 120.1(4) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
O2 C10 O1 109.9(3) . . ?
O2 C10 C11 113.9(4) . . ?
O1 C10 C11 106.8(3) . . ?
O2 C10 C9 103.0(3) . . ?
O1 C10 C9 106.9(4) . . ?
C11 C10 C9 116.0(4) . . ?
C1 C6 C5 118.9(5) . . ?
C1 C6 C7 122.2(4) . . ?
C5 C6 C7 118.9(4) . . ?
N1 C7 O1 126.4(4) . . ?
N1 C7 C6 122.0(4) . . ?
O1 C7 C6 111.6(4) . . ?
C16 C11 C12 118.6(4) . . ?
C16 C11 C10 122.2(4) . . ?
C12 C11 C10 119.1(4) . . ?
C14 C15 C16 120.9(5) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C8 C9 C10 108.2(4) . . ?
C8 C9 Br1 108.8(3) . . ?
C10 C9 Br1 112.0(3) . . ?
C8 C9 Br2 109.0(4) . . ?
C10 C9 Br2 110.2(3) . . ?
Br1 C9 Br2 108.7(2) . . ?
C15 C14 C13 119.6(5) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C4 C5 C6 120.3(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C3 C4 C5 120.4(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N1 C8 C9 114.5(4) . . ?
N1 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
N1 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C6 C1 C2 120.6(5) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C12 C13 C14 120.2(5) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C3 C2 C1 120.0(5) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
O2 C17 C18 108.2(5) . . ?
O2 C17 H17A 110.0 . . ?
C18 C17 H17A 110.0 . . ?
O2 C17 H17B 110.0 . . ?
C18 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C17 O2 C10 O1 54.2(5) . . . . ?
C17 O2 C10 C11 -65.6(5) . . . . ?
C17 O2 C10 C9 167.9(4) . . . . ?
C7 O1 C10 O2 63.7(5) . . . . ?
C7 O1 C10 C11 -172.3(3) . . . . ?
C7 O1 C10 C9 -47.5(5) . . . . ?
C8 N1 C7 O1 -3.0(7) . . . . ?
C8 N1 C7 C6 175.2(4) . . . . ?
C10 O1 C7 N1 20.8(6) . . . . ?
C10 O1 C7 C6 -157.5(4) . . . . ?
C1 C6 C7 N1 -172.9(5) . . . . ?
C5 C6 C7 N1 5.4(7) . . . . ?
C1 C6 C7 O1 5.5(6) . . . . ?
C5 C6 C7 O1 -176.1(4) . . . . ?
C15 C16 C11 C12 -0.8(7) . . . . ?
C15 C16 C11 C10 178.8(4) . . . . ?
O2 C10 C11 C16 151.0(4) . . . . ?
O1 C10 C11 C16 29.4(6) . . . . ?
C9 C10 C11 C16 -89.6(5) . . . . ?
O2 C10 C11 C12 -29.4(6) . . . . ?
O1 C10 C11 C12 -151.0(4) . . . . ?
C9 C10 C11 C12 90.0(5) . . . . ?
C11 C16 C15 C14 1.6(7) . . . . ?
O2 C10 C9 C8 -57.9(5) . . . . ?
O1 C10 C9 C8 58.0(5) . . . . ?
C11 C10 C9 C8 177.0(4) . . . . ?
O2 C10 C9 Br1 62.0(4) . . . . ?
O1 C10 C9 Br1 177.9(3) . . . . ?
C11 C10 C9 Br1 -63.1(4) . . . . ?
O2 C10 C9 Br2 -176.9(3) . . . . ?
O1 C10 C9 Br2 -61.0(4) . . . . ?
C11 C10 C9 Br2 58.0(4) . . . . ?
C16 C15 C14 C13 -1.1(8) . . . . ?
C16 C11 C12 C13 -0.5(7) . . . . ?
C10 C11 C12 C13 179.9(5) . . . . ?
C1 C6 C5 C4 1.2(7) . . . . ?
C7 C6 C5 C4 -177.2(4) . . . . ?
C2 C3 C4 C5 -1.2(8) . . . . ?
C6 C5 C4 C3 -0.2(8) . . . . ?
C7 N1 C8 C9 16.7(7) . . . . ?
C10 C9 C8 N1 -43.9(6) . . . . ?
Br1 C9 C8 N1 -165.8(4) . . . . ?
Br2 C9 C8 N1 75.9(5) . . . . ?
C5 C6 C1 C2 -0.8(8) . . . . ?
C7 C6 C1 C2 177.6(5) . . . . ?
C11 C12 C13 C14 1.0(8) . . . . ?
C15 C14 C13 C12 -0.2(8) . . . . ?
C4 C3 C2 C1 1.6(9) . . . . ?
C6 C1 C2 C3 -0.6(9) . . . . ?
C10 O2 C17 C18 -177.4(5) . . . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.060



