# Electronic Supplementary Material (ESI) 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. 
# 
#######################################################################

data_md_zxjb1
_database_code_depnum_ccdc_archive 'CCDC 2325025'
loop_
_audit_author_name
_audit_author_address
'ZHAO xiaojing'
;Yunnan Minzu University
China
;
_audit_update_record             
;
2024-01-12 deposited with the CCDC.	2024-05-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H11 Br N2 O2'
_chemical_formula_sum            'C16 H11 Br N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         343.18

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.6679(9)
_cell_length_b                   9.0807(3)
_cell_length_c                   10.2318(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.2330(10)
_cell_angle_gamma                90
_cell_volume                     2712.65(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      3.0272
_cell_measurement_theta_max      71.9123
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.180
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376

_exptl_absorpt_coefficient_mu    4.188
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.22
_exptl_absorpt_correction_T_max  0.52

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            12466
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         72.00
_diffrn_reflns_theta_full        72.00
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             2658
_reflns_number_gt                2510
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1449
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_number_reflns         2658
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1094P)²+2.0384P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.828
_refine_diff_density_min         -0.993
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0031(3)

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'
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.51780(2) 0.79784(3) 0.45541(3) 0.0360(2) Uani d . . . 1 . .
O O1 0.74916(7) 0.4015(2) 0.57130(19) 0.0351(5) Uani d . . . 1 . .
O O2 0.70549(6) 0.7353(2) 0.60609(18) 0.0284(4) Uani d . . . 1 . .
N N1 0.71472(8) 0.5457(2) 0.7550(2) 0.0260(5) Uani d . . . 1 . .
N N2 0.65299(9) 0.4090(3) 0.8118(2) 0.0316(5) Uani d . . . 1 . .
C C1 0.54521(9) 0.5616(3) 0.6334(3) 0.0307(6) Uani d . . . 1 . .
H H1 0.51324 0.545599 0.626703 0.037 Uiso calc U . R 1 . .
C C2 0.57615(10) 0.4731(3) 0.7138(3) 0.0320(6) Uani d . . . 1 . .
H H11 0.565408 0.394544 0.761383 0.038 Uiso calc U . R 1 . .
C C3 0.62342(9) 0.4979(3) 0.7259(2) 0.0267(5) Uani d . . . 1 . .
C C4 0.63874(9) 0.6126(3) 0.6520(2) 0.0244(5) Uani d . . . 1 . .
C C5 0.68788(9) 0.6395(3) 0.6650(2) 0.0243(5) Uani d . . . 1 . .
C C6 0.76418(10) 0.5511(3) 0.7653(2) 0.0269(5) Uani d . . . 1 . .
H H4 0.779142 0.511795 0.852485 0.032 Uiso calc U . R 1 . .
H H9 0.774194 0.654343 0.758392 0.032 Uiso calc U . R 1 . .
C C7 0.77819(9) 0.4593(3) 0.6538(2) 0.0261(5) Uani d . . . 1 . .
C C8 0.82803(9) 0.4394(3) 0.6534(2) 0.0274(6) Uani d . . . 1 . .
C C9 0.86117(10) 0.5246(3) 0.7326(3) 0.0325(6) Uani d . . . 1 . .
H H5 0.852178 0.599934 0.787004 0.039 Uiso calc U . R 1 . .
C C10 0.90706(10) 0.4999(4) 0.7322(3) 0.0391(7) Uani d . . . 1 . .
H H8 0.929624 0.558257 0.786126 0.047 Uiso calc U . R 1 . .
C C11 0.92022(11) 0.3888(4) 0.6523(3) 0.0398(7) Uani d . . . 1 . .
H H2 0.951788 0.371654 0.651974 0.048 Uiso calc U . R 1 . .
C C12 0.56137(10) 0.6755(3) 0.5615(3) 0.0277(5) Uani d . . . 1 . .
C C13 0.60754(10) 0.7017(3) 0.5687(3) 0.0264(6) Uani d . . . 1 . .
H H3 0.617916 0.778362 0.518273 0.032 Uiso calc U . R 1 . .
C C14 0.69582(10) 0.4367(3) 0.8221(2) 0.0290(6) Uani d . . . 1 . .
H H10 0.716384 0.376893 0.881226 0.035 Uiso calc U . R 1 . .
C C15 0.88744(12) 0.3036(3) 0.5736(3) 0.0367(7) Uani d . . . 1 . .
H H7 0.896527 0.227981 0.519568 0.044 Uiso calc U . R 1 . .
C C16 0.84125(11) 0.3286(3) 0.5735(3) 0.0317(6) Uani d . . . 1 . .
H H6 0.818709 0.270374 0.519286 0.038 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C12 . 1.894(3) ?
O1 C7 . 1.213(3) ?
O2 C5 . 1.227(3) ?
N1 C14 . 1.379(4) ?
N1 C5 . 1.395(3) ?
N1 C6 . 1.453(3) ?
N2 C14 . 1.281(4) ?
N2 C3 . 1.385(4) ?
C1 C2 . 1.377(4) ?
C1 C12 . 1.402(4) ?
C1 H1 . 0.95 ?
C2 C3 . 1.404(4) ?
C2 H11 . 0.95 ?
C3 C4 . 1.409(4) ?
C4 C13 . 1.399(4) ?
C4 C5 . 1.461(3) ?
C6 C7 . 1.528(3) ?
C6 H4 . 0.99 ?
C6 H9 . 0.99 ?
C7 C8 . 1.490(4) ?
C8 C9 . 1.392(4) ?
C8 C16 . 1.396(4) ?
C9 C10 . 1.380(4) ?
C9 H5 . 0.95 ?
C10 C11 . 1.397(5) ?
C10 H8 . 0.95 ?
C11 C15 . 1.384(5) ?
C11 H2 . 0.95 ?
C12 C13 . 1.379(4) ?
C13 H3 . 0.95 ?
C14 H10 . 0.95 ?
C15 C16 . 1.389(4) ?
C15 H7 . 0.95 ?
C16 H6 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 N1 C5 . . 122.1(2) ?
C14 N1 C6 . . 118.9(2) ?
C5 N1 C6 . . 118.6(2) ?
C14 N2 C3 . . 116.4(2) ?
C2 C1 C12 . . 119.4(2) ?
C2 C1 H1 . . 120.3 ?
C12 C1 H1 . . 120.3 ?
C1 C2 C3 . . 120.6(2) ?
C1 C2 H11 . . 119.7 ?
C3 C2 H11 . . 119.7 ?
N2 C3 C2 . . 118.2(2) ?
N2 C3 C4 . . 122.9(2) ?
C2 C3 C4 . . 118.9(2) ?
C13 C4 C3 . . 120.9(2) ?
C13 C4 C5 . . 120.0(2) ?
C3 C4 C5 . . 119.1(2) ?
O2 C5 N1 . . 120.9(2) ?
O2 C5 C4 . . 125.4(2) ?
N1 C5 C4 . . 113.7(2) ?
N1 C6 C7 . . 109.4(2) ?
N1 C6 H4 . . 109.8 ?
C7 C6 H4 . . 109.8 ?
N1 C6 H9 . . 109.8 ?
C7 C6 H9 . . 109.8 ?
H4 C6 H9 . . 108.2 ?
O1 C7 C8 . . 121.9(2) ?
O1 C7 C6 . . 120.1(3) ?
C8 C7 C6 . . 118.0(2) ?
C9 C8 C16 . . 119.9(3) ?
C9 C8 C7 . . 122.0(2) ?
C16 C8 C7 . . 118.1(3) ?
C10 C9 C8 . . 120.2(3) ?
C10 C9 H5 . . 119.9 ?
C8 C9 H5 . . 119.9 ?
C9 C10 C11 . . 119.8(3) ?
C9 C10 H8 . . 120.1 ?
C11 C10 H8 . . 120.1 ?
C15 C11 C10 . . 120.2(3) ?
C15 C11 H2 . . 119.9 ?
C10 C11 H2 . . 119.9 ?
C13 C12 C1 . . 121.9(3) ?
C13 C12 Br1 . . 120.0(2) ?
C1 C12 Br1 . . 118.1(2) ?
C12 C13 C4 . . 118.4(2) ?
C12 C13 H3 . . 120.8 ?
C4 C13 H3 . . 120.8 ?
N2 C14 N1 . . 125.8(3) ?
N2 C14 H10 . . 117.1 ?
N1 C14 H10 . . 117.1 ?
C11 C15 C16 . . 120.0(3) ?
C11 C15 H7 . . 120.0 ?
C16 C15 H7 . . 120.0 ?
C15 C16 C8 . . 119.8(3) ?
C15 C16 H6 . . 120.1 ?
C8 C16 H6 . . 120.1 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 C1 C2 C3 . . . . 1.2(4) ?
C14 N2 C3 C2 . . . . -178.7(2) ?
C14 N2 C3 C4 . . . . 0.5(4) ?
C1 C2 C3 N2 . . . . 177.7(2) ?
C1 C2 C3 C4 . . . . -1.5(4) ?
N2 C3 C4 C13 . . . . -178.6(2) ?
C2 C3 C4 C13 . . . . 0.6(4) ?
N2 C3 C4 C5 . . . . 0.4(4) ?
C2 C3 C4 C5 . . . . 179.6(2) ?
C14 N1 C5 O2 . . . . -179.7(2) ?
C6 N1 C5 O2 . . . . -7.6(3) ?
C14 N1 C5 C4 . . . . 1.2(3) ?
C6 N1 C5 C4 . . . . 173.2(2) ?
C13 C4 C5 O2 . . . . -1.3(4) ?
C3 C4 C5 O2 . . . . 179.8(2) ?
C13 C4 C5 N1 . . . . 177.8(2) ?
C3 C4 C5 N1 . . . . -1.1(3) ?
C14 N1 C6 C7 . . . . 90.6(3) ?
C5 N1 C6 C7 . . . . -81.7(3) ?
N1 C6 C7 O1 . . . . 3.1(3) ?
N1 C6 C7 C8 . . . . -174.7(2) ?
O1 C7 C8 C9 . . . . 168.7(3) ?
C6 C7 C8 C9 . . . . -13.6(4) ?
O1 C7 C8 C16 . . . . -13.2(4) ?
C6 C7 C8 C16 . . . . 164.5(2) ?
C16 C8 C9 C10 . . . . 0.1(4) ?
C7 C8 C9 C10 . . . . 178.1(3) ?
C8 C9 C10 C11 . . . . -0.1(4) ?
C9 C10 C11 C15 . . . . 0.0(5) ?
C2 C1 C12 C13 . . . . 0.1(4) ?
C2 C1 C12 Br1 . . . . -178.5(2) ?
C1 C12 C13 C4 . . . . -1.0(4) ?
Br1 C12 C13 C4 . . . . 177.60(18) ?
C3 C4 C13 C12 . . . . 0.6(4) ?
C5 C4 C13 C12 . . . . -178.3(2) ?
C3 N2 C14 N1 . . . . -0.5(4) ?
C5 N1 C14 N2 . . . . -0.4(4) ?
C6 N1 C14 N2 . . . . -172.4(2) ?
C10 C11 C15 C16 . . . . 0.2(4) ?
C11 C15 C16 C8 . . . . -0.2(4) ?
C9 C8 C16 C15 . . . . 0.1(4) ?
C7 C8 C16 C15 . . . . -178.0(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H4 O2 4_646 0.99 2.57 3.216(3) 122.5 ?
C14 H10 O2 4_646 0.95 2.63 3.420(3) 140.4 ?
C14 H10 O2 6_566 0.95 2.59 3.266(3) 128.6 ?



