# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_3aa-1
_database_code_depnum_ccdc_archive 'CCDC 2357898'
loop_
_audit_author_name
_audit_author_address
'Kai Zhang'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-08-02 downloaded from the CCDC.
;
_audit_creation_date             2023-11-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 Br F2 N O2'
_chemical_formula_sum            'C25 H20 Br F2 N O2'
_chemical_formula_weight         484.33
_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 0.0033 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'
F F 0.0171 0.0103 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.1467(5)
_cell_length_b                   10.3698(5)
_cell_length_c                   11.2435(5)
_cell_angle_alpha                75.044(2)
_cell_angle_beta                 76.595(2)
_cell_angle_gamma                76.840(2)
_cell_volume                     1093.94(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.62
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.917
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            80960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.885
_diffrn_reflns_theta_min         2.066
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4191
_reflns_number_total             7468
_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         1.134
_refine_diff_density_min         -1.119
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         7468
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1403
_refine_ls_R_factor_gt           0.0820
_refine_ls_restrained_S_all      1.023
_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)+(0.0735P)²+1.7433P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1896
_refine_ls_wR_factor_ref         0.2325
_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:
 C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C24(H24), C25(H25)
;
_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 0.83653(8) 0.09693(6) 1.28252(5) 0.1128(3) Uani 1 1 d . . . . .
F1 F 0.6402(3) 0.6933(3) 0.5401(3) 0.0918(9) Uani 1 1 d . . . . .
F2 F 0.7936(4) 0.5804(3) 0.6493(2) 0.0880(9) Uani 1 1 d . . . . .
O1 O 0.5397(3) 0.4502(3) 0.7867(3) 0.0777(9) Uani 1 1 d . . . . .
O2 O 0.9253(4) 0.6892(4) 0.4058(4) 0.0966(12) Uani 1 1 d . . . . .
N1 N 0.8398(3) 0.5252(3) 0.3604(3) 0.0546(7) Uani 1 1 d . . . . .
C1 C 0.7857(6) 0.7603(5) 0.1454(5) 0.0812(13) Uani 1 1 d . . . . .
H1 H 0.794742 0.789150 0.214364 0.097 Uiso 1 1 calc R U . . .
C2 C 0.7210(6) 0.8508(6) 0.0545(5) 0.0925(16) Uani 1 1 d . . . . .
H2 H 0.685853 0.939829 0.062305 0.111 Uiso 1 1 calc R U . . .
C3 C 0.7090(6) 0.8087(9) -0.0472(5) 0.106(2) Uani 1 1 d . . . . .
H3 H 0.666657 0.869784 -0.109674 0.128 Uiso 1 1 calc R U . . .
C4 C 0.7580(6) 0.6791(10) -0.0580(5) 0.115(2) Uani 1 1 d . . . . .
H4 H 0.749119 0.651685 -0.127764 0.138 Uiso 1 1 calc R U . . .
C5 C 0.8214(5) 0.5865(6) 0.0339(5) 0.0818(14) Uani 1 1 d . . . . .
H5 H 0.853211 0.496851 0.026703 0.098 Uiso 1 1 calc R U . . .
C6 C 0.8372(4) 0.6278(5) 0.1362(3) 0.0607(9) Uani 1 1 d . . . . .
C7 C 0.9150(5) 0.5302(5) 0.2324(4) 0.0702(11) Uani 1 1 d . . . . .
H7A H 0.933863 0.440135 0.215297 0.084 Uiso 1 1 calc R U . . .
H7B H 1.002610 0.557203 0.224654 0.084 Uiso 1 1 calc R U . . .
C8 C 0.8501(4) 0.6071(4) 0.4302(4) 0.0585(9) Uani 1 1 d . . . . .
C9 C 0.7430(4) 0.5833(4) 0.5471(3) 0.0531(8) Uani 1 1 d . . . . .
C10 C 0.6897(4) 0.4570(4) 0.5516(3) 0.0499(8) Uani 1 1 d . . . . .
H10 H 0.588981 0.478790 0.562811 0.060 Uiso 1 1 calc R U . . .
C11 C 0.7474(5) 0.4310(4) 0.4197(3) 0.0659(11) Uani 1 1 d . . . . .
H11A H 0.796249 0.338371 0.423854 0.079 Uiso 1 1 calc R U . . .
H11B H 0.673675 0.446130 0.373340 0.079 Uiso 1 1 calc R U . . .
C12 C 0.7299(3) 0.3396(3) 0.6586(3) 0.0450(7) Uani 1 1 d . . . . .
H12 H 0.828307 0.330199 0.657962 0.054 Uiso 1 1 calc R U . . .
C13 C 0.7021(4) 0.2057(4) 0.6475(3) 0.0545(8) Uani 1 1 d . . . . .
C14 C 0.5688(6) 0.1870(5) 0.6601(5) 0.0795(13) Uani 1 1 d . . . . .
H14 H 0.495267 0.255530 0.678009 0.095 Uiso 1 1 calc R U . . .
C15 C 0.5450(9) 0.0666(7) 0.6461(6) 0.112(2) Uani 1 1 d . . . . .
H15 H 0.455105 0.054652 0.653638 0.134 Uiso 1 1 calc R U . . .
C16 C 0.6514(12) -0.0345(6) 0.6214(6) 0.122(3) Uani 1 1 d . . . . .
H16 H 0.634160 -0.115145 0.611645 0.147 Uiso 1 1 calc R U . . .
C17 C 0.7837(10) -0.0184(5) 0.6109(5) 0.106(2) Uani 1 1 d . . . . .
H17 H 0.856334 -0.088655 0.595599 0.127 Uiso 1 1 calc R U . . .
C18 C 0.8101(6) 0.1024(4) 0.6231(4) 0.0739(12) Uani 1 1 d . . . . .
H18 H 0.900278 0.113825 0.614825 0.089 Uiso 1 1 calc R U . . .
C19 C 0.6488(4) 0.3717(4) 0.7830(3) 0.0494(7) Uani 1 1 d . . . . .
C20 C 0.7004(3) 0.3024(3) 0.9011(3) 0.0463(7) Uani 1 1 d . . . . .
C21 C 0.6135(4) 0.3168(5) 1.0137(4) 0.0665(11) Uani 1 1 d . . . . .
H21 H 0.525425 0.367894 1.012861 0.080 Uiso 1 1 calc R U . . .
C22 C 0.6546(5) 0.2572(5) 1.1264(4) 0.0744(12) Uani 1 1 d . . . . .
H22 H 0.595156 0.267487 1.201190 0.089 Uiso 1 1 calc R U . . .
C23 C 0.7835(5) 0.1828(4) 1.1270(3) 0.0665(11) Uani 1 1 d . . . . .
C24 C 0.8751(5) 0.1688(4) 1.0173(4) 0.0674(11) Uani 1 1 d . . . . .
H24 H 0.964198 0.120663 1.019396 0.081 Uiso 1 1 calc R U . . .
C25 C 0.8323(4) 0.2277(4) 0.9043(3) 0.0565(9) Uani 1 1 d . . . . .
H25 H 0.892262 0.217122 0.829820 0.068 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 C23 1.886(4) . ?
F1 C9 1.358(4) . ?
F2 C9 1.353(4) . ?
O1 C19 1.215(4) . ?
O2 C8 1.209(5) . ?
N1 C7 1.458(5) . ?
N1 C8 1.331(5) . ?
N1 C11 1.438(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.375(7) . ?
C1 C6 1.376(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.348(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(6) . ?
C6 C7 1.512(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.504(6) . ?
C9 C10 1.512(5) . ?
C10 H10 0.9800 . ?
C10 C11 1.533(5) . ?
C10 C12 1.530(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9800 . ?
C12 C13 1.519(5) . ?
C12 C19 1.526(4) . ?
C13 C14 1.379(6) . ?
C13 C18 1.378(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.356(11) . ?
C16 H16 0.9300 . ?
C16 C17 1.365(11) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.488(5) . ?
C20 C21 1.386(5) . ?
C20 C25 1.389(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.359(7) . ?
C23 C24 1.380(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.382(5) . ?
C25 H25 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
C8 N1 C7 123.0(4) . . ?
C8 N1 C11 115.2(3) . . ?
C11 N1 C7 121.7(3) . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C6 121.2(5) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(6) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.5(6) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(5) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.7(6) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 118.5(5) . . ?
C1 C6 C7 121.2(4) . . ?
C5 C6 C7 120.2(4) . . ?
N1 C7 C6 112.8(3) . . ?
N1 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
O2 C8 N1 128.4(4) . . ?
O2 C8 C9 125.1(4) . . ?
N1 C8 C9 106.4(3) . . ?
F1 C9 C8 107.7(3) . . ?
F1 C9 C10 110.6(3) . . ?
F2 C9 F1 104.8(3) . . ?
F2 C9 C8 110.8(3) . . ?
F2 C9 C10 114.7(3) . . ?
C8 C9 C10 108.1(3) . . ?
C9 C10 H10 108.6 . . ?
C9 C10 C11 102.7(3) . . ?
C9 C10 C12 112.8(3) . . ?
C11 C10 H10 108.6 . . ?
C12 C10 H10 108.6 . . ?
C12 C10 C11 115.2(3) . . ?
N1 C11 C10 106.0(3) . . ?
N1 C11 H11A 110.5 . . ?
N1 C11 H11B 110.5 . . ?
C10 C11 H11A 110.5 . . ?
C10 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C10 C12 H12 108.7 . . ?
C13 C12 C10 112.6(3) . . ?
C13 C12 H12 108.7 . . ?
C13 C12 C19 108.8(3) . . ?
C19 C12 C10 109.2(3) . . ?
C19 C12 H12 108.7 . . ?
C14 C13 C12 120.3(4) . . ?
C18 C13 C12 120.2(4) . . ?
C18 C13 C14 119.5(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(6) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(7) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(6) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(6) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 119.8(6) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
O1 C19 C12 120.3(3) . . ?
O1 C19 C20 119.7(3) . . ?
C20 C19 C12 120.0(3) . . ?
C21 C20 C19 118.1(3) . . ?
C21 C20 C25 118.4(3) . . ?
C25 C20 C19 123.4(3) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 C20 121.4(4) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 119.0(4) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 Br1 118.5(3) . . ?
C22 C23 C24 121.7(4) . . ?
C24 C23 Br1 119.8(3) . . ?
C23 C24 H24 120.6 . . ?
C23 C24 C25 118.9(4) . . ?
C25 C24 H24 120.6 . . ?
C20 C25 H25 119.7 . . ?
C24 C25 C20 120.6(3) . . ?
C24 C25 H25 119.7 . . ?

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
Br1 C23 C24 C25 177.2(3) . . . . ?
F1 C9 C10 C11 105.5(4) . . . . ?
F1 C9 C10 C12 -129.9(3) . . . . ?
F2 C9 C10 C11 -136.3(4) . . . . ?
F2 C9 C10 C12 -11.7(5) . . . . ?
O1 C19 C20 C21 8.0(6) . . . . ?
O1 C19 C20 C25 -169.9(4) . . . . ?
O2 C8 C9 F1 70.2(5) . . . . ?
O2 C8 C9 F2 -43.8(6) . . . . ?
O2 C8 C9 C10 -170.3(4) . . . . ?
N1 C8 C9 F1 -107.2(3) . . . . ?
N1 C8 C9 F2 138.7(3) . . . . ?
N1 C8 C9 C10 12.3(4) . . . . ?
C1 C2 C3 C4 1.0(9) . . . . ?
C1 C6 C7 N1 52.4(6) . . . . ?
C2 C1 C6 C5 -0.7(7) . . . . ?
C2 C1 C6 C7 176.7(5) . . . . ?
C2 C3 C4 C5 0.0(10) . . . . ?
C3 C4 C5 C6 -1.4(9) . . . . ?
C4 C5 C6 C1 1.7(7) . . . . ?
C4 C5 C6 C7 -175.7(5) . . . . ?
C5 C6 C7 N1 -130.2(4) . . . . ?
C6 C1 C2 C3 -0.6(8) . . . . ?
C7 N1 C8 O2 -5.1(7) . . . . ?
C7 N1 C8 C9 172.2(3) . . . . ?
C7 N1 C11 C10 179.9(3) . . . . ?
C8 N1 C7 C6 -89.2(5) . . . . ?
C8 N1 C11 C10 -0.6(5) . . . . ?
C8 C9 C10 C11 -12.2(4) . . . . ?
C8 C9 C10 C12 112.5(3) . . . . ?
C9 C10 C11 N1 8.0(4) . . . . ?
C9 C10 C12 C13 -168.3(3) . . . . ?
C9 C10 C12 C19 70.7(4) . . . . ?
C10 C12 C13 C14 -66.7(4) . . . . ?
C10 C12 C13 C18 112.5(4) . . . . ?
C10 C12 C19 O1 24.2(5) . . . . ?
C10 C12 C19 C20 -158.4(3) . . . . ?
C11 N1 C7 C6 90.2(5) . . . . ?
C11 N1 C8 O2 175.5(5) . . . . ?
C11 N1 C8 C9 -7.2(5) . . . . ?
C11 C10 C12 C13 -50.8(4) . . . . ?
C11 C10 C12 C19 -171.8(3) . . . . ?
C12 C10 C11 N1 -115.0(4) . . . . ?
C12 C13 C14 C15 178.0(4) . . . . ?
C12 C13 C18 C17 -178.8(4) . . . . ?
C12 C19 C20 C21 -169.4(4) . . . . ?
C12 C19 C20 C25 12.7(5) . . . . ?
C13 C12 C19 O1 -99.1(4) . . . . ?
C13 C12 C19 C20 78.3(4) . . . . ?
C13 C14 C15 C16 0.8(9) . . . . ?
C14 C13 C18 C17 0.3(6) . . . . ?
C14 C15 C16 C17 0.4(10) . . . . ?
C15 C16 C17 C18 -1.2(9) . . . . ?
C16 C17 C18 C13 0.9(7) . . . . ?
C18 C13 C14 C15 -1.1(7) . . . . ?
C19 C12 C13 C14 54.5(4) . . . . ?
C19 C12 C13 C18 -126.4(3) . . . . ?
C19 C20 C21 C22 -179.2(4) . . . . ?
C19 C20 C25 C24 178.2(4) . . . . ?
C20 C21 C22 C23 0.2(7) . . . . ?
C21 C20 C25 C24 0.3(6) . . . . ?
C21 C22 C23 Br1 -178.1(4) . . . . ?
C21 C22 C23 C24 1.8(7) . . . . ?
C22 C23 C24 C25 -2.6(7) . . . . ?
C23 C24 C25 C20 1.6(7) . . . . ?
C25 C20 C21 C22 -1.1(7) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3aa-2
_database_code_depnum_ccdc_archive 'CCDC 2357899'
loop_
_audit_author_name
_audit_author_address
'Kai Zhang'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2024-05-24 deposited with the CCDC.	2024-08-02 downloaded from the CCDC.
;
_audit_creation_date             2023-11-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 Br F2 N O2'
_chemical_formula_sum            'C25 H20 Br F2 N O2'
_chemical_formula_weight         484.33
_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 0.0033 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'
F F 0.0171 0.0103 '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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7990(13)
_cell_length_b                   25.874(4)
_cell_length_c                   10.0568(14)
_cell_angle_alpha                90
_cell_angle_beta                 103.338(8)
_cell_angle_gamma                90
_cell_volume                     2227.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9843
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.913
_cell_measurement_theta_min      2.225
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.883
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_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    1.444
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            54833
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.629
_diffrn_reflns_theta_min         2.506
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3861
_reflns_number_total             5663
_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         0.742
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         5663
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0632
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0747P)²+1.9866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1815
_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:
 C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C24(H24), C25(H25)
;
_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 0.78640(6) 0.49207(2) 1.16865(4) 0.0850(2) Uani 1 1 d . . . . .
F1 F 0.9273(3) 0.73693(10) 0.5439(3) 0.0851(7) Uani 1 1 d . . . . .
F2 F 0.9340(4) 0.70622(11) 0.3454(3) 0.0994(9) Uani 1 1 d . . . . .
O1 O 0.7308(5) 0.79382(13) 0.3058(4) 0.1070(13) Uani 1 1 d . . . . .
O2 O 0.6360(3) 0.57407(10) 0.5087(2) 0.0553(6) Uani 1 1 d . . . . .
N1 N 0.5771(4) 0.73799(12) 0.3928(3) 0.0652(8) Uani 1 1 d . . . . .
C1 C 0.2548(6) 0.79601(19) 0.4998(6) 0.0866(14) Uani 1 1 d . . . . .
H1 H 0.182694 0.771289 0.458044 0.104 Uiso 1 1 calc R U . . .
C2 C 0.2199(8) 0.8286(3) 0.5959(7) 0.112(2) Uani 1 1 d . . . . .
H2 H 0.122854 0.826053 0.617379 0.134 Uiso 1 1 calc R U . . .
C3 C 0.3219(10) 0.8640(3) 0.6597(6) 0.109(2) Uani 1 1 d . . . . .
H3 H 0.296358 0.885349 0.725581 0.131 Uiso 1 1 calc R U . . .
C4 C 0.4638(8) 0.8685(2) 0.6273(7) 0.1054(19) Uani 1 1 d . . . . .
H4 H 0.535076 0.893026 0.671310 0.126 Uiso 1 1 calc R U . . .
C5 C 0.5018(6) 0.83671(18) 0.5298(5) 0.0846(13) Uani 1 1 d . . . . .
H5 H 0.598111 0.840050 0.507395 0.102 Uiso 1 1 calc R U . . .
C6 C 0.3964(5) 0.79991(14) 0.4652(4) 0.0648(10) Uani 1 1 d . . . . .
C7 C 0.4296(6) 0.76624(17) 0.3544(5) 0.0783(12) Uani 1 1 d . . . . .
H7A H 0.345133 0.741554 0.327588 0.094 Uiso 1 1 calc R U . . .
H7B H 0.431301 0.787578 0.275401 0.094 Uiso 1 1 calc R U . . .
C8 C 0.7091(6) 0.75417(16) 0.3656(4) 0.0733(11) Uani 1 1 d . . . . .
C9 C 0.8366(5) 0.71548(15) 0.4282(4) 0.0662(10) Uani 1 1 d . . . . .
C10 C 0.7503(4) 0.66805(12) 0.4588(3) 0.0486(7) Uani 1 1 d . . . . .
H10 H 0.731107 0.645636 0.378106 0.058 Uiso 1 1 calc R U . . .
C11 C 0.5919(4) 0.69038(13) 0.4727(4) 0.0546(8) Uani 1 1 d . . . . .
H11A H 0.507194 0.666705 0.435903 0.065 Uiso 1 1 calc R U . . .
H11B H 0.592645 0.697540 0.567554 0.065 Uiso 1 1 calc R U . . .
C12 C 0.8357(3) 0.63622(11) 0.5819(3) 0.0416(6) Uani 1 1 d . . . . .
H12 H 0.857640 0.658310 0.663285 0.050 Uiso 1 1 calc R U . . .
C13 C 0.9884(3) 0.61403(12) 0.5607(3) 0.0430(6) Uani 1 1 d . . . . .
C14 C 1.1305(4) 0.63084(15) 0.6365(4) 0.0581(9) Uani 1 1 d . . . . .
H14 H 1.134364 0.655768 0.703866 0.070 Uiso 1 1 calc R U . . .
C15 C 1.2680(4) 0.61068(18) 0.6127(5) 0.0710(11) Uani 1 1 d . . . . .
H15 H 1.363500 0.622521 0.663764 0.085 Uiso 1 1 calc R U . . .
C16 C 1.2649(4) 0.57384(17) 0.5157(5) 0.0691(11) Uani 1 1 d . . . . .
H16 H 1.357585 0.560405 0.500849 0.083 Uiso 1 1 calc R U . . .
C17 C 1.1244(5) 0.55671(17) 0.4401(5) 0.0688(10) Uani 1 1 d . . . . .
H17 H 1.121487 0.531764 0.372965 0.083 Uiso 1 1 calc R U . . .
C18 C 0.9869(4) 0.57637(14) 0.4631(4) 0.0559(8) Uani 1 1 d . . . . .
H18 H 0.891912 0.564074 0.412185 0.067 Uiso 1 1 calc R U . . .
C19 C 0.7318(3) 0.59176(11) 0.6044(3) 0.0404(6) Uani 1 1 d . . . . .
C20 C 0.7507(3) 0.56918(11) 0.7440(3) 0.0416(6) Uani 1 1 d . . . . .
C21 C 0.6522(4) 0.52935(14) 0.7612(4) 0.0533(8) Uani 1 1 d . . . . .
H21 H 0.577997 0.517273 0.686257 0.064 Uiso 1 1 calc R U . . .
C22 C 0.6624(5) 0.50722(14) 0.8879(4) 0.0612(9) Uani 1 1 d . . . . .
H22 H 0.594205 0.480927 0.898598 0.073 Uiso 1 1 calc R U . . .
C23 C 0.7734(4) 0.52424(14) 0.9971(3) 0.0544(8) Uani 1 1 d . . . . .
C24 C 0.8724(5) 0.56360(17) 0.9835(4) 0.0681(10) Uani 1 1 d . . . . .
H24 H 0.946972 0.575191 1.058842 0.082 Uiso 1 1 calc R U . . .
C25 C 0.8608(4) 0.58595(15) 0.8571(4) 0.0585(9) Uani 1 1 d . . . . .
H25 H 0.928102 0.612718 0.847779 0.070 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 C23 1.895(3) . ?
F1 C9 1.368(5) . ?
F2 C9 1.347(4) . ?
O1 C8 1.227(5) . ?
O2 C19 1.213(4) . ?
N1 C7 1.462(5) . ?
N1 C8 1.321(5) . ?
N1 C11 1.460(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.370(8) . ?
C1 C6 1.372(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.337(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.366(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(6) . ?
C6 C7 1.496(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.527(6) . ?
C9 C10 1.512(5) . ?
C10 H10 0.9800 . ?
C10 C11 1.544(5) . ?
C10 C12 1.532(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9800 . ?
C12 C13 1.521(4) . ?
C12 C19 1.519(4) . ?
C13 C14 1.376(5) . ?
C13 C18 1.381(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.360(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.367(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.494(4) . ?
C20 C21 1.382(4) . ?
C20 C25 1.383(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.381(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.364(6) . ?
C23 C24 1.367(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.378(5) . ?
C25 H25 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
C8 N1 C7 123.8(3) . . ?
C8 N1 C11 114.2(3) . . ?
C11 N1 C7 121.9(3) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.9(5) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.6(6) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(6) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.2(6) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.9(5) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 118.8(4) . . ?
C1 C6 C7 119.4(4) . . ?
C5 C6 C7 121.7(4) . . ?
N1 C7 C6 114.1(4) . . ?
N1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
O1 C8 N1 127.6(4) . . ?
O1 C8 C9 124.6(4) . . ?
N1 C8 C9 107.7(3) . . ?
F1 C9 C8 108.3(3) . . ?
F1 C9 C10 112.2(3) . . ?
F2 C9 F1 105.6(4) . . ?
F2 C9 C8 111.9(3) . . ?
F2 C9 C10 113.8(3) . . ?
C10 C9 C8 105.1(3) . . ?
C9 C10 H10 108.1 . . ?
C9 C10 C11 102.8(3) . . ?
C9 C10 C12 115.2(3) . . ?
C11 C10 H10 108.1 . . ?
C12 C10 H10 108.1 . . ?
C12 C10 C11 114.4(2) . . ?
N1 C11 C10 103.5(3) . . ?
N1 C11 H11A 111.1 . . ?
N1 C11 H11B 111.1 . . ?
C10 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
H11A C11 H11B 109.0 . . ?
C10 C12 H12 109.1 . . ?
C13 C12 C10 112.0(2) . . ?
C13 C12 H12 109.1 . . ?
C19 C12 C10 109.1(3) . . ?
C19 C12 H12 109.1 . . ?
C19 C12 C13 108.5(2) . . ?
C14 C13 C12 121.5(3) . . ?
C14 C13 C18 118.4(3) . . ?
C18 C13 C12 120.1(3) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.1(4) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(4) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.5(3) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(4) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 121.0(3) . . ?
C17 C18 H18 119.5 . . ?
O2 C19 C12 120.0(3) . . ?
O2 C19 C20 120.3(3) . . ?
C20 C19 C12 119.7(3) . . ?
C21 C20 C19 118.1(3) . . ?
C21 C20 C25 118.1(3) . . ?
C25 C20 C19 123.7(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 Br1 118.2(3) . . ?
C22 C23 C24 120.9(3) . . ?
C24 C23 Br1 120.8(3) . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.4(4) . . ?
C25 C24 H24 120.3 . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 121.0(3) . . ?
C24 C25 H25 119.5 . . ?

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
Br1 C23 C24 C25 179.5(3) . . . . ?
F1 C9 C10 C11 93.1(4) . . . . ?
F1 C9 C10 C12 -31.9(4) . . . . ?
F2 C9 C10 C11 -147.1(4) . . . . ?
F2 C9 C10 C12 87.9(4) . . . . ?
O1 C8 C9 F1 73.2(5) . . . . ?
O1 C8 C9 F2 -42.8(6) . . . . ?
O1 C8 C9 C10 -166.8(4) . . . . ?
O2 C19 C20 C21 -2.6(4) . . . . ?
O2 C19 C20 C25 177.6(3) . . . . ?
N1 C8 C9 F1 -104.4(4) . . . . ?
N1 C8 C9 F2 139.6(4) . . . . ?
N1 C8 C9 C10 15.7(4) . . . . ?
C1 C2 C3 C4 1.0(10) . . . . ?
C1 C6 C7 N1 -128.8(4) . . . . ?
C2 C1 C6 C5 0.5(7) . . . . ?
C2 C1 C6 C7 -176.5(4) . . . . ?
C2 C3 C4 C5 -0.1(9) . . . . ?
C3 C4 C5 C6 -0.5(8) . . . . ?
C4 C5 C6 C1 0.3(7) . . . . ?
C4 C5 C6 C7 177.2(4) . . . . ?
C5 C6 C7 N1 54.3(5) . . . . ?
C6 C1 C2 C3 -1.2(9) . . . . ?
C7 N1 C8 O1 -0.1(7) . . . . ?
C7 N1 C8 C9 177.3(4) . . . . ?
C7 N1 C11 C10 167.0(3) . . . . ?
C8 N1 C7 C6 -95.7(5) . . . . ?
C8 N1 C11 C10 -16.4(4) . . . . ?
C8 C9 C10 C11 -24.3(4) . . . . ?
C8 C9 C10 C12 -149.4(3) . . . . ?
C9 C10 C11 N1 24.4(4) . . . . ?
C9 C10 C12 C13 -62.8(3) . . . . ?
C9 C10 C12 C19 177.1(3) . . . . ?
C10 C12 C13 C14 112.0(3) . . . . ?
C10 C12 C13 C18 -67.6(4) . . . . ?
C10 C12 C19 O2 27.9(4) . . . . ?
C10 C12 C19 C20 -153.6(2) . . . . ?
C11 N1 C7 C6 80.6(5) . . . . ?
C11 N1 C8 O1 -176.7(5) . . . . ?
C11 N1 C8 C9 0.7(5) . . . . ?
C11 C10 C12 C13 178.4(3) . . . . ?
C11 C10 C12 C19 58.3(3) . . . . ?
C12 C10 C11 N1 150.0(3) . . . . ?
C12 C13 C14 C15 -178.5(3) . . . . ?
C12 C13 C18 C17 178.3(3) . . . . ?
C12 C19 C20 C21 178.9(3) . . . . ?
C12 C19 C20 C25 -1.0(4) . . . . ?
C13 C12 C19 O2 -94.4(3) . . . . ?
C13 C12 C19 C20 84.2(3) . . . . ?
C13 C14 C15 C16 -0.7(6) . . . . ?
C14 C13 C18 C17 -1.2(5) . . . . ?
C14 C15 C16 C17 0.4(7) . . . . ?
C15 C16 C17 C18 -0.6(7) . . . . ?
C16 C17 C18 C13 1.0(6) . . . . ?
C18 C13 C14 C15 1.0(5) . . . . ?
C19 C12 C13 C14 -127.5(3) . . . . ?
C19 C12 C13 C18 52.9(4) . . . . ?
C19 C20 C21 C22 -179.2(3) . . . . ?
C19 C20 C25 C24 179.9(3) . . . . ?
C20 C21 C22 C23 -1.3(6) . . . . ?
C21 C20 C25 C24 0.1(5) . . . . ?
C21 C22 C23 Br1 -178.9(3) . . . . ?
C21 C22 C23 C24 1.4(6) . . . . ?
C22 C23 C24 C25 -0.7(6) . . . . ?
C23 C24 C25 C20 0.0(6) . . . . ?
C25 C20 C21 C22 0.6(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
