# 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_mo_dd22075_0m
_database_code_depnum_ccdc_archive 'CCDC 2342669'
loop_
_audit_author_name
_audit_author_address
Yang
;ECUST
China
;
_audit_update_record             
;
2024-03-23 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Br N2 O3'
_chemical_formula_weight         373.20

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                   4.8026(3)
_cell_length_b                   10.1124(6)
_cell_length_c                   31.8117(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1544.96(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3126
_cell_measurement_theta_min      4.733
_cell_measurement_theta_max      54.101

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    2.677
_shelx_estimated_absorpt_T_min   0.644
_shelx_estimated_absorpt_T_max   0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4356
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7304
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.783
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3004
_reflns_number_gt                2395
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.990

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0270P)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 827 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.047(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3004
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0974
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
Br1 Br -0.47125(10) 0.50339(5) 0.47197(2) 0.0577(2) Uani 1 1 d . . . . .
O1 O 0.4452(7) 0.2821(3) 0.62575(9) 0.0488(8) Uani 1 1 d . . . . .
O2 O 0.6669(10) 0.6578(3) 0.65800(12) 0.0792(13) Uani 1 1 d . . . . .
O3 O 0.9690(10) 0.5804(4) 0.70231(13) 0.0830(13) Uani 1 1 d . . . . .
N1 N 0.3544(8) 0.4977(4) 0.61647(11) 0.0521(9) Uani 1 1 d . . . . .
H1 H 0.3819 0.5771 0.6252 0.062 Uiso 1 1 calc R U . . .
N2 N 0.7795(11) 0.5622(5) 0.67624(13) 0.0628(13) Uani 1 1 d . . . . .
C1 C 0.6227(10) 0.1791(4) 0.63807(14) 0.0449(11) Uani 1 1 d . . . . .
C2 C 0.5906(12) 0.0620(5) 0.61672(14) 0.0518(12) Uani 1 1 d . . . . .
H2 H 0.4607 0.0543 0.5952 0.062 Uiso 1 1 calc R U . . .
C3 C 0.7544(12) -0.0433(5) 0.62790(16) 0.0578(14) Uani 1 1 d . . . . .
H3 H 0.7351 -0.1234 0.6139 0.069 Uiso 1 1 calc R U . . .
C4 C 0.9473(12) -0.0316(5) 0.65973(16) 0.0601(13) Uani 1 1 d . . . . .
H4 H 1.0563 -0.1037 0.6673 0.072 Uiso 1 1 calc R U . . .
C5 C 0.9780(12) 0.0872(5) 0.68019(15) 0.0563(13) Uani 1 1 d . . . . .
H5 H 1.1116 0.0952 0.7012 0.068 Uiso 1 1 calc R U . . .
C6 C 0.8123(10) 0.1959(4) 0.67004(14) 0.0456(11) Uani 1 1 d . . . . .
C7 C 0.8308(11) 0.3247(5) 0.69327(14) 0.0509(12) Uani 1 1 d . . . . .
H7 H 1.0283 0.3463 0.6969 0.061 Uiso 1 1 calc R U . . .
C8 C 0.6996(12) 0.4326(5) 0.66760(14) 0.0478(12) Uani 1 1 d . . . . .
C9 C 0.5049(10) 0.4067(4) 0.63696(13) 0.0441(11) Uani 1 1 d . . . . .
C10 C 0.7022(13) 0.3099(5) 0.73645(16) 0.0645(15) Uani 1 1 d . . . . .
H10 H 0.7772 0.2444 0.7536 0.077 Uiso 1 1 calc R U . . .
C11 C 0.4998(14) 0.3781(6) 0.75223(17) 0.0706(15) Uani 1 1 d . . . . .
H11A H 0.4169 0.4448 0.7365 0.085 Uiso 1 1 calc R U . . .
H11B H 0.4371 0.3603 0.7793 0.085 Uiso 1 1 calc R U . . .
C12 C 0.1600(9) 0.4890(5) 0.58347(12) 0.0446(10) Uani 1 1 d . . . . .
C13 C 0.0683(14) 0.6090(4) 0.56747(16) 0.0546(14) Uani 1 1 d . . . . .
H13 H 0.1358 0.6872 0.5790 0.066 Uiso 1 1 calc R U . . .
C14 C -0.1204(13) 0.6147(5) 0.53500(15) 0.0567(14) Uani 1 1 d . . . . .
H14 H -0.1801 0.6959 0.5246 0.068 Uiso 1 1 calc R U . . .
C15 C -0.2194(8) 0.4991(5) 0.51812(13) 0.0458(9) Uani 1 1 d . . . . .
C16 C -0.1374(11) 0.3786(5) 0.53404(14) 0.0507(13) Uani 1 1 d . . . . .
H16 H -0.2094 0.3008 0.5229 0.061 Uiso 1 1 calc R U . . .
C17 C 0.0525(13) 0.3737(4) 0.56669(14) 0.0501(13) Uani 1 1 d . . . . .
H17 H 0.1082 0.2924 0.5774 0.060 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 C15 1.903(4) . ?
O1 C9 1.341(5) . ?
O1 C1 1.401(5) . ?
O2 N2 1.251(5) . ?
O3 N2 1.245(5) . ?
N1 C9 1.340(5) . ?
N1 C12 1.408(5) . ?
N1 H1 0.8600 . ?
N2 C8 1.392(6) . ?
C1 C2 1.374(6) . ?
C1 C6 1.375(6) . ?
C2 C3 1.371(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.500(6) . ?
C7 C8 1.502(7) . ?
C7 C10 1.514(7) . ?
C7 H7 0.9800 . ?
C8 C9 1.376(6) . ?
C10 C11 1.293(8) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?
C12 C17 1.382(6) . ?
C12 C13 1.387(6) . ?
C13 C14 1.375(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(6) . ?
C16 C17 1.383(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?

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
C9 O1 C1 119.6(4) . . ?
C9 N1 C12 132.7(4) . . ?
C9 N1 H1 113.7 . . ?
C12 N1 H1 113.7 . . ?
O3 N2 O2 120.7(4) . . ?
O3 N2 C8 118.2(4) . . ?
O2 N2 C8 121.1(5) . . ?
C2 C1 C6 123.1(4) . . ?
C2 C1 O1 115.7(4) . . ?
C6 C1 O1 121.2(4) . . ?
C3 C2 C1 118.5(5) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.7(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.2(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 116.8(4) . . ?
C1 C6 C7 120.7(4) . . ?
C5 C6 C7 122.4(4) . . ?
C6 C7 C8 109.8(4) . . ?
C6 C7 C10 109.7(4) . . ?
C8 C7 C10 113.2(4) . . ?
C6 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C10 C7 H7 108.0 . . ?
C9 C8 N2 120.4(4) . . ?
C9 C8 C7 122.1(4) . . ?
N2 C8 C7 117.4(4) . . ?
N1 C9 O1 113.6(4) . . ?
N1 C9 C8 125.5(4) . . ?
O1 C9 C8 120.9(4) . . ?
C11 C10 C7 127.3(5) . . ?
C11 C10 H10 116.3 . . ?
C7 C10 H10 116.3 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C17 C12 C13 118.5(4) . . ?
C17 C12 N1 126.0(4) . . ?
C13 C12 N1 115.4(4) . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 119.1(4) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.7(4) . . ?
C14 C15 Br1 120.2(4) . . ?
C16 C15 Br1 119.1(4) . . ?
C15 C16 C17 119.8(4) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 120.4(4) . . ?
C12 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?

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
C9 O1 C1 C2 -163.6(4) . . . . ?
C9 O1 C1 C6 17.5(6) . . . . ?
C6 C1 C2 C3 0.3(7) . . . . ?
O1 C1 C2 C3 -178.7(4) . . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
C3 C4 C5 C6 1.6(8) . . . . ?
C2 C1 C6 C5 0.6(7) . . . . ?
O1 C1 C6 C5 179.5(4) . . . . ?
C2 C1 C6 C7 -177.8(4) . . . . ?
O1 C1 C6 C7 1.1(7) . . . . ?
C4 C5 C6 C1 -1.5(7) . . . . ?
C4 C5 C6 C7 176.8(5) . . . . ?
C1 C6 C7 C8 -19.5(6) . . . . ?
C5 C6 C7 C8 162.3(5) . . . . ?
C1 C6 C7 C10 105.5(5) . . . . ?
C5 C6 C7 C10 -72.7(6) . . . . ?
O3 N2 C8 C9 -175.5(4) . . . . ?
O2 N2 C8 C9 3.6(8) . . . . ?
O3 N2 C8 C7 5.3(7) . . . . ?
O2 N2 C8 C7 -175.5(5) . . . . ?
C6 C7 C8 C9 22.8(6) . . . . ?
C10 C7 C8 C9 -100.1(5) . . . . ?
C6 C7 C8 N2 -158.0(5) . . . . ?
C10 C7 C8 N2 79.0(6) . . . . ?
C12 N1 C9 O1 -5.2(7) . . . . ?
C12 N1 C9 C8 176.4(5) . . . . ?
C1 O1 C9 N1 167.2(4) . . . . ?
C1 O1 C9 C8 -14.4(6) . . . . ?
N2 C8 C9 N1 -7.8(8) . . . . ?
C7 C8 C9 N1 171.3(5) . . . . ?
N2 C8 C9 O1 173.9(5) . . . . ?
C7 C8 C9 O1 -7.0(7) . . . . ?
C6 C7 C10 C11 -122.7(6) . . . . ?
C8 C7 C10 C11 0.2(8) . . . . ?
C9 N1 C12 C17 7.8(8) . . . . ?
C9 N1 C12 C13 -173.3(5) . . . . ?
C17 C12 C13 C14 -1.5(7) . . . . ?
N1 C12 C13 C14 179.6(5) . . . . ?
C12 C13 C14 C15 -0.1(8) . . . . ?
C13 C14 C15 C16 1.7(7) . . . . ?
C13 C14 C15 Br1 -177.9(4) . . . . ?
C14 C15 C16 C17 -1.7(7) . . . . ?
Br1 C15 C16 C17 177.9(4) . . . . ?
C13 C12 C17 C16 1.4(7) . . . . ?
N1 C12 C17 C16 -179.8(4) . . . . ?
C15 C16 C17 C12 0.1(8) . . . . ?

_refine_diff_density_max         0.460
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_zm_e123_0m
_database_code_depnum_ccdc_archive 'CCDC 2342670'
loop_
_audit_author_name
_audit_author_address
Yang
;ECUST
China
;
_audit_update_record             
;
2024-03-23 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_audit_creation_date             2024-03-21
_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         'C12 H9 Br N2 O'
_chemical_formula_sum            'C12 H9 Br N2 O'
_chemical_formula_weight         277.12
_chemical_absolute_configuration ad
_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 0.0181 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'

_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                   4.9753(2)
_cell_length_b                   16.0176(6)
_cell_length_c                   14.3810(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.798(2)
_cell_angle_gamma                90
_cell_volume                     1145.94(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      68.394
_cell_measurement_theta_min      4.131
_shelx_estimated_absorpt_T_max   0.579
_shelx_estimated_absorpt_T_min   0.452
_exptl_absorpt_coefficient_mu    4.724
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1444 before and 0.0859 after correction.
The Ratio of minimum to maximum transmission is 0.7065.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_av_unetI/netI     0.1122
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14310
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.389
_diffrn_reflns_theta_min         3.073
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                3382
_reflns_number_total             4023
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 
;
 Flack x determined using 1324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.070
_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)+(0.0751P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1216
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H) groups
2. Restrained distances
 C12B-H12D
 0.82 with sigma of 0.02
3.a Rotating group:
 N1A(H1AA,H1AB), N1B(H1BA,H1BB)
3.b Ternary CH refined with riding coordinates:
 C3A(H3A), C3B(H3B)
3.c Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C5A(H5A), C7B(H7B), C7A(H7A), C11B(H11B), C5B(H5B), C6B(H6B),
 C11A(H11A)
;
_atom_sites_solution_hydrogens   mixed
_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
Br1A Br 1.58694(16) 0.82258(4) 0.31012(4) 0.0559(3) Uani 1 1 d . . . . .
Br1B Br -0.5979(2) 0.17690(4) 0.19008(5) 0.0680(3) Uani 1 1 d . . . . .
O1A O 1.1746(10) 0.6882(4) 0.3298(3) 0.0440(12) Uani 1 1 d . . . . .
O1B O -0.2258(9) 0.3227(4) 0.1725(3) 0.0470(11) Uani 1 1 d . . . . .
N2B N 0.5012(13) 0.5106(4) 0.1366(4) 0.0493(16) Uani 1 1 d . . . . .
C9A C 1.2415(13) 0.7184(5) 0.4179(4) 0.0366(14) Uani 1 1 d . . . . .
C4A C 1.1303(13) 0.6879(5) 0.4979(4) 0.0390(15) Uani 1 1 d . . . . .
N1A N 0.9302(13) 0.6127(5) 0.2315(4) 0.0503(16) Uani 1 1 d . . . . .
H1AA H 0.781815 0.584470 0.224689 0.060 Uiso 1 1 d R U . . .
H1AB H 0.915115 0.658341 0.199029 0.060 Uiso 1 1 d R U . . .
C6A C 1.4104(16) 0.7826(6) 0.5863(4) 0.052(2) Uani 1 1 d . . . . .
H6A H 1.469054 0.802581 0.643785 0.063 Uiso 1 1 calc R U . . .
C10A C 0.6374(14) 0.5416(5) 0.3788(4) 0.0405(16) Uani 1 1 d . . . . .
C8A C 1.4340(14) 0.7808(5) 0.4208(4) 0.0433(16) Uani 1 1 d . . . . .
C5A C 1.2159(15) 0.7224(5) 0.5821(4) 0.0476(18) Uani 1 1 d . . . . .
H5A H 1.138815 0.703951 0.636924 0.057 Uiso 1 1 calc R U . . .
N1B N 0.0514(14) 0.3876(5) 0.2718(4) 0.0510(16) Uani 1 1 d . . . . .
H1BA H -0.031822 0.350505 0.305234 0.061 Uiso 1 1 d R U . . .
H1BB H 0.223651 0.380882 0.281794 0.061 Uiso 1 1 d R U . . .
C7B C -0.5004(19) 0.1824(7) -0.0042(6) 0.0562(19) Uani 1 1 d . . . . .
H7B H -0.608429 0.135079 -0.007089 0.067 Uiso 1 1 calc R U . . .
C2B C 0.0983(13) 0.4125(5) 0.1070(4) 0.0400(14) Uani 1 1 d . . . . .
C1A C 0.9761(14) 0.6317(5) 0.3221(4) 0.0375(14) Uani 1 1 d . . . . .
C1B C -0.0157(14) 0.3767(5) 0.1816(4) 0.0400(15) Uani 1 1 d . . . . .
C3A C 0.9149(13) 0.6220(4) 0.4955(3) 0.0390(13) Uani 1 1 d . . . . .
H3A H 0.754033 0.645288 0.524212 0.047 Uiso 1 1 calc R U . . .
C2A C 0.8431(13) 0.5987(5) 0.3956(4) 0.0400(15) Uani 1 1 d . . . . .
C3B C -0.0227(14) 0.4063(5) 0.0093(4) 0.0452(15) Uani 1 1 d . . . . .
H3B H -0.153324 0.451663 0.001817 0.054 Uiso 1 1 calc R U . . .
C7A C 1.5209(16) 0.8142(7) 0.5058(5) 0.054(2) Uani 1 1 d . . . . .
H7A H 1.649149 0.856388 0.508174 0.064 Uiso 1 1 calc R U . . .
N2A N 0.4665(14) 0.4949(5) 0.3659(4) 0.058(2) Uani 1 1 d . . . . .
C11B C 0.1798(17) 0.4154(6) -0.0644(4) 0.064(2) Uani 1 1 d . . . . .
H11B H 0.310190 0.374067 -0.068943 0.077 Uiso 1 1 calc R U . . .
C5B C -0.2321(15) 0.2854(6) -0.0802(4) 0.0483(18) Uani 1 1 d . . . . .
H5B H -0.160649 0.306653 -0.134771 0.058 Uiso 1 1 calc R U . . .
C4B C -0.1758(13) 0.3242(6) 0.0044(4) 0.0434(15) Uani 1 1 d . . . . .
C12B C 0.189(3) 0.4771(9) -0.1234(6) 0.100(5) Uani 1 1 d D . . . .
H12C H 0.27(3) 0.485(10) -0.176(8) 0.150 Uiso 1 1 d . U . . .
H12D H 0.06(2) 0.506(10) -0.105(10) 0.150 Uiso 1 1 d D U . . .
C10B C 0.3219(15) 0.4668(5) 0.1229(4) 0.0403(15) Uani 1 1 d . . . . .
C8B C -0.4454(15) 0.2205(5) 0.0807(4) 0.0487(19) Uani 1 1 d . . . . .
C9B C -0.2806(14) 0.2894(5) 0.0850(4) 0.0413(16) Uani 1 1 d . . . . .
C12A C 0.865(3) 0.5137(9) 0.6201(7) 0.080(3) Uani 1 1 d . . . . .
H12A H 0.90(3) 0.469(9) 0.656(9) 0.120 Uiso 1 1 d . U . . .
H12B H 0.68(3) 0.525(10) 0.631(8) 0.120 Uiso 1 1 d . U . . .
C6B C -0.3948(18) 0.2150(5) -0.0833(5) 0.055(2) Uani 1 1 d . . . . .
H6B H -0.432372 0.189672 -0.140254 0.066 Uiso 1 1 calc R U . . .
C11A C 1.0002(15) 0.5453(4) 0.5510(4) 0.0492(16) Uani 1 1 d . . . . .
H11A H 1.159591 0.519083 0.534780 0.059 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
Br1A C8A 1.896(7) . ?
Br1B C8B 1.889(8) . ?
O1A C9A 1.392(7) . ?
O1A C1A 1.343(9) . ?
O1B C1B 1.362(9) . ?
O1B C9B 1.391(7) . ?
N2B C10B 1.150(10) . ?
C9A C4A 1.373(10) . ?
C9A C8A 1.385(10) . ?
C4A C5A 1.392(8) . ?
C4A C3A 1.504(10) . ?
N1A H1AA 0.8700 . ?
N1A H1AB 0.8701 . ?
N1A C1A 1.354(7) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.367(11) . ?
C6A C7A 1.384(11) . ?
C10A C2A 1.391(10) . ?
C10A N2A 1.146(9) . ?
C8A C7A 1.397(9) . ?
C5A H5A 0.9300 . ?
N1B H1BA 0.8720 . ?
N1B H1BB 0.8735 . ?
N1B C1B 1.346(7) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.389(10) . ?
C7B C6B 1.364(13) . ?
C2B C1B 1.348(10) . ?
C2B C3B 1.525(7) . ?
C2B C10B 1.428(10) . ?
C1A C2A 1.361(10) . ?
C3A H3A 0.9800 . ?
C3A C2A 1.522(7) . ?
C3A C11A 1.522(8) . ?
C3B H3B 0.9800 . ?
C3B C11B 1.479(10) . ?
C3B C4B 1.520(11) . ?
C7A H7A 0.9300 . ?
C11B H11B 0.9300 . ?
C11B C12B 1.303(15) . ?
C5B H5B 0.9300 . ?
C5B C4B 1.391(9) . ?
C5B C6B 1.389(12) . ?
C4B C9B 1.394(10) . ?
C12B H12C 0.86(13) . ?
C12B H12D 0.83(3) . ?
C8B C9B 1.376(11) . ?
C12A H12A 0.90(14) . ?
C12A H12B 0.93(13) . ?
C12A C11A 1.310(13) . ?
C6B H6B 0.9300 . ?
C11A H11A 0.9300 . ?

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
C1A O1A C9A 118.3(5) . . ?
C1B O1B C9B 118.1(5) . . ?
C4A C9A O1A 123.0(6) . . ?
C4A C9A C8A 121.2(5) . . ?
C8A C9A O1A 115.8(6) . . ?
C9A C4A C5A 117.7(7) . . ?
C9A C4A C3A 121.7(5) . . ?
C5A C4A C3A 120.5(6) . . ?
H1AA N1A H1AB 108.0 . . ?
C1A N1A H1AA 110.9 . . ?
C1A N1A H1AB 109.9 . . ?
C5A C6A H6A 119.7 . . ?
C5A C6A C7A 120.7(6) . . ?
C7A C6A H6A 119.7 . . ?
N2A C10A C2A 179.1(8) . . ?
C9A C8A Br1A 121.0(5) . . ?
C9A C8A C7A 120.6(7) . . ?
C7A C8A Br1A 118.4(6) . . ?
C4A C5A H5A 119.1 . . ?
C6A C5A C4A 121.8(7) . . ?
C6A C5A H5A 119.1 . . ?
H1BA N1B H1BB 107.4 . . ?
C1B N1B H1BA 109.3 . . ?
C1B N1B H1BB 111.8 . . ?
C8B C7B H7B 120.2 . . ?
C6B C7B H7B 120.2 . . ?
C6B C7B C8B 119.5(9) . . ?
C1B C2B C3B 122.7(6) . . ?
C1B C2B C10B 117.8(5) . . ?
C10B C2B C3B 119.0(6) . . ?
O1A C1A N1A 110.1(6) . . ?
O1A C1A C2A 124.2(5) . . ?
N1A C1A C2A 125.6(7) . . ?
N1B C1B O1B 110.7(6) . . ?
N1B C1B C2B 127.6(7) . . ?
C2B C1B O1B 121.6(5) . . ?
C4A C3A H3A 108.0 . . ?
C4A C3A C2A 110.6(5) . . ?
C4A C3A C11A 111.1(5) . . ?
C2A C3A H3A 108.0 . . ?
C2A C3A C11A 111.0(5) . . ?
C11A C3A H3A 108.0 . . ?
C10A C2A C3A 119.2(6) . . ?
C1A C2A C10A 119.0(5) . . ?
C1A C2A C3A 121.8(6) . . ?
C2B C3B H3B 107.8 . . ?
C11B C3B C2B 112.9(5) . . ?
C11B C3B H3B 107.8 . . ?
C11B C3B C4B 113.5(6) . . ?
C4B C3B C2B 106.9(5) . . ?
C4B C3B H3B 107.8 . . ?
C6A C7A C8A 118.0(8) . . ?
C6A C7A H7A 121.0 . . ?
C8A C7A H7A 121.0 . . ?
C3B C11B H11B 117.6 . . ?
C12B C11B C3B 124.9(11) . . ?
C12B C11B H11B 117.6 . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C6B C5B C4B 120.1(8) . . ?
C5B C4B C3B 121.4(7) . . ?
C5B C4B C9B 118.4(8) . . ?
C9B C4B C3B 120.0(6) . . ?
C11B C12B H12C 135(10) . . ?
C11B C12B H12D 101(10) . . ?
H12C C12B H12D 123(10) . . ?
N2B C10B C2B 179.3(7) . . ?
C7B C8B Br1B 119.6(7) . . ?
C9B C8B Br1B 120.4(5) . . ?
C9B C8B C7B 120.1(8) . . ?
O1B C9B C4B 121.9(7) . . ?
C8B C9B O1B 117.2(6) . . ?
C8B C9B C4B 120.9(6) . . ?
H12A C12A H12B 104(10) . . ?
C11A C12A H12A 130(9) . . ?
C11A C12A H12B 124(8) . . ?
C7B C6B C5B 121.0(7) . . ?
C7B C6B H6B 119.5 . . ?
C5B C6B H6B 119.5 . . ?
C3A C11A H11A 117.7 . . ?
C12A C11A C3A 124.5(9) . . ?
C12A C11A H11A 117.7 . . ?

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
Br1A C8A C7A C6A -179.3(7) . . . . ?
Br1B C8B C9B O1B 2.2(9) . . . . ?
Br1B C8B C9B C4B -177.3(6) . . . . ?
O1A C9A C4A C5A 179.2(6) . . . . ?
O1A C9A C4A C3A -3.3(11) . . . . ?
O1A C9A C8A Br1A 1.2(9) . . . . ?
O1A C9A C8A C7A -178.5(7) . . . . ?
O1A C1A C2A C10A 178.9(7) . . . . ?
O1A C1A C2A C3A -1.7(12) . . . . ?
C9A O1A C1A N1A 177.0(6) . . . . ?
C9A O1A C1A C2A -3.2(11) . . . . ?
C9A C4A C5A C6A -2.2(12) . . . . ?
C9A C4A C3A C2A -1.4(9) . . . . ?
C9A C4A C3A C11A 122.4(7) . . . . ?
C9A C8A C7A C6A 0.5(13) . . . . ?
C4A C9A C8A Br1A 180.0(6) . . . . ?
C4A C9A C8A C7A 0.2(11) . . . . ?
C4A C3A C2A C10A -176.8(6) . . . . ?
C4A C3A C2A C1A 3.8(9) . . . . ?
C4A C3A C11A C12A 123.4(9) . . . . ?
N1A C1A C2A C10A -1.3(12) . . . . ?
N1A C1A C2A C3A 178.1(7) . . . . ?
C8A C9A C4A C5A 0.6(11) . . . . ?
C8A C9A C4A C3A 178.1(6) . . . . ?
C5A C4A C3A C2A 176.1(7) . . . . ?
C5A C4A C3A C11A -60.2(9) . . . . ?
C5A C6A C7A C8A -2.0(14) . . . . ?
C7B C8B C9B O1B -177.7(7) . . . . ?
C7B C8B C9B C4B 2.7(12) . . . . ?
C2B C3B C11B C12B -114.3(9) . . . . ?
C2B C3B C4B C5B -157.8(7) . . . . ?
C2B C3B C4B C9B 27.0(9) . . . . ?
C1A O1A C9A C4A 5.8(11) . . . . ?
C1A O1A C9A C8A -175.6(6) . . . . ?
C1B O1B C9B C4B -16.3(10) . . . . ?
C1B O1B C9B C8B 164.2(7) . . . . ?
C1B C2B C3B C11B -154.5(8) . . . . ?
C1B C2B C3B C4B -29.1(10) . . . . ?
C3A C4A C5A C6A -179.7(7) . . . . ?
C2A C3A C11A C12A -113.1(9) . . . . ?
C3B C2B C1B O1B 9.6(12) . . . . ?
C3B C2B C1B N1B -170.0(8) . . . . ?
C3B C4B C9B O1B -7.0(10) . . . . ?
C3B C4B C9B C8B 172.5(7) . . . . ?
C7A C6A C5A C4A 2.9(14) . . . . ?
C11B C3B C4B C5B -32.7(9) . . . . ?
C11B C3B C4B C9B 152.1(7) . . . . ?
C5B C4B C9B O1B 177.7(6) . . . . ?
C5B C4B C9B C8B -2.8(11) . . . . ?
C4B C3B C11B C12B 123.9(10) . . . . ?
C4B C5B C6B C7B -0.4(13) . . . . ?
C10B C2B C1B O1B -178.5(7) . . . . ?
C10B C2B C1B N1B 1.9(13) . . . . ?
C10B C2B C3B C11B 33.7(10) . . . . ?
C10B C2B C3B C4B 159.1(6) . . . . ?
C8B C7B C6B C5B 0.3(15) . . . . ?
C9B O1B C1B N1B -165.2(7) . . . . ?
C9B O1B C1B C2B 15.1(11) . . . . ?
C6B C7B C8B Br1B 178.6(7) . . . . ?
C6B C7B C8B C9B -1.5(14) . . . . ?
C6B C5B C4B C3B -173.6(7) . . . . ?
C6B C5B C4B C9B 1.6(12) . . . . ?
C11A C3A C2A C10A 59.4(8) . . . . ?
C11A C3A C2A C1A -120.0(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
