# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_4381
_database_code_depnum_ccdc_archive 'CCDC 2290686'
loop_
_audit_author_name
_audit_author_address
'zouzj indole'
;Southwest Minzu University
China
;
_audit_update_record             
;
2023-08-25 deposited with the CCDC.	2023-11-03 downloaded from the CCDC.
;
_audit_creation_date             2022-12-30
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 Br N3 O2'
_chemical_formula_sum            'C25 H22 Br N3 O2'
_chemical_formula_weight         476.36
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   5.1550(3)
_cell_length_b                   8.0069(4)
_cell_length_c                   50.226(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2073.11(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6811
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.6270
_cell_measurement_theta_min      3.4520
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.931
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       61
_diffrn_reflns_limit_l_min       -62
_diffrn_reflns_number            11527
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.834
_diffrn_reflns_theta_min         3.520
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -11.00   1.00    1.00    --  -40.92 -67.00-155.00  103
  2  ω   -113.00 -61.00   1.00    1.00    --  -40.92-144.00 -28.00   52
  3  ω     23.00  97.00   1.00    1.00    --   40.92-125.00-120.00   74
  4  ω     31.00 136.00   1.00    1.00    --  107.58 -30.00  30.00  105
  5  ω     25.00 109.00   1.00    1.00    --  107.58 -94.00 -60.00   84
  6  ω     94.00 178.00   1.00    1.00    --  107.58 125.00 120.00   84
  7  ω     35.00 133.00   1.00    1.00    --  107.58 -45.00 -60.00   98
  8  ω     26.00 160.00   1.00    1.00    --  107.58 -15.00-180.00  134
  9  ω     34.00 122.00   1.00    1.00    --  107.58-125.00-120.00   88
 10  ω   -113.00 -74.00   1.00    1.00    --  -40.92 -57.00 -60.00   39
 11  ω   -113.00 -13.00   1.00    1.00    --  -40.92 -57.00  30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0040566000
_diffrn_orient_matrix_UB_12      0.0138683000
_diffrn_orient_matrix_UB_13      -0.0305817000
_diffrn_orient_matrix_UB_21      0.2287669000
_diffrn_orient_matrix_UB_22      0.1235552000
_diffrn_orient_matrix_UB_23      0.0011466000
_diffrn_orient_matrix_UB_31      0.1925821000
_diffrn_orient_matrix_UB_32      -0.1467882000
_diffrn_orient_matrix_UB_33      -0.0019477000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                3967
_reflns_number_total             4112
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.097
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 
;
 Flack x determined using 1396 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.032
_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)+16.3811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1362
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N2(H2)
2.b Ternary CH refined with riding coordinates:
 C9(H9), C11(H11)
2.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C19(H19A,H19B)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2A), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15),
 C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_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
Br1 Br 0.94016(18) 1.09459(11) 0.24337(2) 0.0326(2) Uani 1 1 d . . . . .
O1 O 0.5616(11) 0.8991(7) 0.44076(8) 0.0227(10) Uani 1 1 d . . . . .
O2 O 0.8757(9) 0.8697(7) 0.40917(10) 0.0206(12) Uani 1 1 d . . . . .
N1 N 0.0717(15) 0.2078(8) 0.39252(13) 0.0272(15) Uani 1 1 d . . . . .
H1 H -0.032088 0.120537 0.392364 0.033 Uiso 1 1 calc R U . . .
N2 N 0.1999(13) 0.7596(8) 0.32688(12) 0.0229(15) Uani 1 1 d . . . . .
H2 H 0.145574 0.743465 0.310903 0.027 Uiso 1 1 d R U . . .
N3 N 0.4613(14) 0.7778(8) 0.40236(11) 0.0185(13) Uani 1 1 d . . . . .
H3 H 0.287(19) 0.779(12) 0.4085(19) 0.03(3) Uiso 1 1 d . . . . .
C1 C 0.2659(17) 0.2362(11) 0.41070(16) 0.0281(18) Uani 1 1 d . . . . .
H1A H 0.309798 0.163919 0.425006 0.034 Uiso 1 1 calc R U . . .
C2 C 0.3858(14) 0.3833(10) 0.40511(14) 0.0206(16) Uani 1 1 d . . . . .
H2A H 0.525797 0.431562 0.414694 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2606(14) 0.4524(9) 0.38189(14) 0.0152(15) Uani 1 1 d . . . . .
C4 C 0.0654(17) 0.3387(9) 0.37445(14) 0.0206(15) Uani 1 1 d . . . . .
C5 C -0.0884(16) 0.3629(9) 0.35173(15) 0.0226(16) Uani 1 1 d . . . . .
H5 H -0.224244 0.287963 0.347159 0.027 Uiso 1 1 calc R U . . .
C6 C -0.0324(16) 0.5007(9) 0.33642(14) 0.0221(16) Uani 1 1 d . . . . .
H6 H -0.127427 0.517418 0.320441 0.027 Uiso 1 1 calc R U . . .
C7 C 0.1595(14) 0.6182(9) 0.34336(13) 0.0178(15) Uani 1 1 d . . . . .
C8 C 0.3077(13) 0.5970(10) 0.36666(12) 0.0157(13) Uani 1 1 d . . . . .
C9 C 0.5106(14) 0.7220(9) 0.37476(12) 0.0164(15) Uani 1 1 d . . . . .
H9 H 0.683772 0.665774 0.374240 0.020 Uiso 1 1 calc R U . . .
C10 C 0.5202(16) 0.8747(9) 0.35634(13) 0.0225(17) Uani 1 1 d . . . . .
H10A H 0.390744 0.958010 0.362334 0.027 Uiso 1 1 calc R U . . .
H10B H 0.693971 0.926885 0.357428 0.027 Uiso 1 1 calc R U . . .
C11 C 0.4638(17) 0.8260(9) 0.32750(13) 0.0201(15) Uani 1 1 d . . . . .
H11 H 0.587638 0.736476 0.321911 0.024 Uiso 1 1 calc R U . . .
C12 C 0.4925(15) 0.9750(9) 0.30895(13) 0.0203(16) Uani 1 1 d . . . . .
C13 C 0.3479(16) 1.1193(11) 0.31277(15) 0.0278(18) Uani 1 1 d . . . . .
H13 H 0.221571 1.123029 0.326529 0.033 Uiso 1 1 calc R U . . .
C14 C 0.3864(19) 1.2589(11) 0.29660(17) 0.033(2) Uani 1 1 d . . . . .
H14 H 0.291174 1.358356 0.299916 0.039 Uiso 1 1 calc R U . . .
C15 C 0.5613(18) 1.2538(10) 0.27586(14) 0.0253(16) Uani 1 1 d . . . . .
H15 H 0.585352 1.347660 0.264556 0.030 Uiso 1 1 calc R U . . .
C16 C 0.7009(15) 1.1082(10) 0.27193(14) 0.0209(15) Uani 1 1 d . . . . .
C17 C 0.6671(15) 0.9698(10) 0.28817(14) 0.0201(16) Uani 1 1 d . . . . .
H17 H 0.764576 0.871174 0.284962 0.024 Uiso 1 1 calc R U . . .
C18 C 0.6514(15) 0.8498(9) 0.41644(14) 0.0166(15) Uani 1 1 d . . . . .
C19 C 0.7478(17) 0.9849(11) 0.45734(15) 0.0283(19) Uani 1 1 d . . . . .
H19A H 0.773799 1.100230 0.450778 0.034 Uiso 1 1 calc R U . . .
H19B H 0.916624 0.926062 0.456773 0.034 Uiso 1 1 calc R U . . .
C20 C 0.6468(15) 0.9884(10) 0.48529(14) 0.0201(16) Uani 1 1 d . . . . .
C21 C 0.7845(15) 0.9053(12) 0.50514(15) 0.0252(16) Uani 1 1 d . . . . .
H21 H 0.936729 0.844444 0.500725 0.030 Uiso 1 1 calc R U . . .
C22 C 0.6995(17) 0.9113(13) 0.53141(15) 0.0306(19) Uani 1 1 d . . . . .
H22 H 0.795317 0.855570 0.544908 0.037 Uiso 1 1 calc R U . . .
C23 C 0.4767(18) 0.9976(10) 0.53798(15) 0.0293(19) Uani 1 1 d . . . . .
H23 H 0.419162 1.001177 0.555942 0.035 Uiso 1 1 calc R U . . .
C24 C 0.3380(16) 1.0787(11) 0.51835(16) 0.0268(17) Uani 1 1 d . . . . .
H24 H 0.183302 1.136796 0.522783 0.032 Uiso 1 1 calc R U . . .
C25 C 0.4238(17) 1.0756(10) 0.49209(14) 0.0253(16) Uani 1 1 d . . . . .
H25 H 0.329194 1.133567 0.478741 0.030 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 C16 1.895(7) . ?
O1 C18 1.365(8) . ?
O1 C19 1.444(9) . ?
O2 C18 1.223(9) . ?
N1 H1 0.8800 . ?
N1 C1 1.374(11) . ?
N1 C4 1.387(9) . ?
N2 H2 0.8598 . ?
N2 C7 1.418(9) . ?
N2 C11 1.461(11) . ?
N3 H3 0.95(10) . ?
N3 C9 1.478(8) . ?
N3 C18 1.339(10) . ?
C1 H1A 0.9500 . ?
C1 C2 1.359(11) . ?
C2 H2A 0.9500 . ?
C2 C3 1.443(10) . ?
C3 C4 1.408(11) . ?
C3 C8 1.408(10) . ?
C4 C5 1.403(11) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(10) . ?
C6 H6 0.9500 . ?
C6 C7 1.409(10) . ?
C7 C8 1.408(9) . ?
C8 C9 1.504(10) . ?
C9 H9 1.0000 . ?
C9 C10 1.534(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.528(9) . ?
C11 H11 1.0000 . ?
C11 C12 1.521(9) . ?
C12 C13 1.388(11) . ?
C12 C17 1.379(10) . ?
C13 H13 0.9500 . ?
C13 C14 1.396(12) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(12) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(11) . ?
C16 C17 1.387(11) . ?
C17 H17 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.497(10) . ?
C20 C21 1.393(11) . ?
C20 C25 1.388(11) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(11) . ?
C22 H22 0.9500 . ?
C22 C23 1.380(12) . ?
C23 H23 0.9500 . ?
C23 C24 1.380(12) . ?
C24 H24 0.9500 . ?
C24 C25 1.391(10) . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O1 C19 115.3(6) . . ?
C1 N1 H1 125.5 . . ?
C1 N1 C4 109.1(7) . . ?
C4 N1 H1 125.5 . . ?
C7 N2 H2 112.2 . . ?
C7 N2 C11 114.5(6) . . ?
C11 N2 H2 112.2 . . ?
C9 N3 H3 118(6) . . ?
C18 N3 H3 121(6) . . ?
C18 N3 C9 120.0(6) . . ?
N1 C1 H1A 125.1 . . ?
C2 C1 N1 109.7(7) . . ?
C2 C1 H1A 125.1 . . ?
C1 C2 H2A 126.4 . . ?
C1 C2 C3 107.2(7) . . ?
C3 C2 H2A 126.4 . . ?
C4 C3 C2 106.6(6) . . ?
C4 C3 C8 120.7(6) . . ?
C8 C3 C2 132.6(7) . . ?
N1 C4 C3 107.4(7) . . ?
N1 C4 C5 130.5(8) . . ?
C5 C4 C3 122.1(7) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 C4 116.5(7) . . ?
C6 C5 H5 121.7 . . ?
C5 C6 H6 118.5 . . ?
C5 C6 C7 123.0(7) . . ?
C7 C6 H6 118.5 . . ?
C6 C7 N2 119.5(6) . . ?
C8 C7 N2 120.1(7) . . ?
C8 C7 C6 120.4(7) . . ?
C3 C8 C9 121.3(6) . . ?
C7 C8 C3 117.2(7) . . ?
C7 C8 C9 121.5(7) . . ?
N3 C9 C8 109.6(6) . . ?
N3 C9 H9 108.3 . . ?
N3 C9 C10 109.2(6) . . ?
C8 C9 H9 108.3 . . ?
C8 C9 C10 112.9(6) . . ?
C10 C9 H9 108.3 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C9 111.2(6) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
N2 C11 C10 106.9(6) . . ?
N2 C11 H11 109.1 . . ?
N2 C11 C12 111.3(6) . . ?
C10 C11 H11 109.1 . . ?
C12 C11 C10 111.2(6) . . ?
C12 C11 H11 109.1 . . ?
C13 C12 C11 121.0(6) . . ?
C17 C12 C11 120.3(7) . . ?
C17 C12 C13 118.7(7) . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(7) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.6(8) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.9 . . ?
C14 C15 C16 118.2(7) . . ?
C16 C15 H15 120.9 . . ?
C15 C16 Br1 119.7(6) . . ?
C15 C16 C17 121.6(7) . . ?
C17 C16 Br1 118.7(6) . . ?
C12 C17 C16 120.2(7) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
O2 C18 O1 123.4(7) . . ?
O2 C18 N3 126.2(7) . . ?
N3 C18 O1 110.4(6) . . ?
O1 C19 H19A 110.0 . . ?
O1 C19 H19B 110.0 . . ?
O1 C19 C20 108.6(6) . . ?
H19A C19 H19B 108.4 . . ?
C20 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
C21 C20 C19 119.0(7) . . ?
C25 C20 C19 121.9(7) . . ?
C25 C20 C21 119.1(7) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.1(8) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(8) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.7(7) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.3(8) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 120.4(7) . . ?
C20 C25 H25 119.8 . . ?
C24 C25 H25 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
Br1 C16 C17 C12 -179.3(6) . . . . ?
O1 C19 C20 C21 116.5(9) . . . . ?
O1 C19 C20 C25 -65.2(10) . . . . ?
N1 C1 C2 C3 -0.2(9) . . . . ?
N1 C4 C5 C6 -174.5(8) . . . . ?
N2 C7 C8 C3 -179.0(6) . . . . ?
N2 C7 C8 C9 0.1(10) . . . . ?
N2 C11 C12 C13 61.5(9) . . . . ?
N2 C11 C12 C17 -119.7(8) . . . . ?
N3 C9 C10 C11 -157.6(6) . . . . ?
C1 N1 C4 C3 -0.6(9) . . . . ?
C1 N1 C4 C5 176.6(8) . . . . ?
C1 C2 C3 C4 -0.2(8) . . . . ?
C1 C2 C3 C8 -177.2(8) . . . . ?
C2 C3 C4 N1 0.5(8) . . . . ?
C2 C3 C4 C5 -177.0(7) . . . . ?
C2 C3 C8 C7 174.1(7) . . . . ?
C2 C3 C8 C9 -5.0(12) . . . . ?
C3 C4 C5 C6 2.4(11) . . . . ?
C3 C8 C9 N3 -54.8(9) . . . . ?
C3 C8 C9 C10 -176.8(6) . . . . ?
C4 N1 C1 C2 0.5(9) . . . . ?
C4 C3 C8 C7 -2.6(10) . . . . ?
C4 C3 C8 C9 178.3(6) . . . . ?
C4 C5 C6 C7 -3.1(11) . . . . ?
C5 C6 C7 N2 -178.1(7) . . . . ?
C5 C6 C7 C8 0.9(11) . . . . ?
C6 C7 C8 C3 2.0(10) . . . . ?
C6 C7 C8 C9 -179.0(6) . . . . ?
C7 N2 C11 C10 -59.5(8) . . . . ?
C7 N2 C11 C12 178.9(6) . . . . ?
C7 C8 C9 N3 126.2(7) . . . . ?
C7 C8 C9 C10 4.2(9) . . . . ?
C8 C3 C4 N1 177.9(6) . . . . ?
C8 C3 C4 C5 0.4(11) . . . . ?
C8 C9 C10 C11 -35.4(9) . . . . ?
C9 N3 C18 O1 177.0(6) . . . . ?
C9 N3 C18 O2 -3.4(12) . . . . ?
C9 C10 C11 N2 62.5(8) . . . . ?
C9 C10 C11 C12 -175.9(6) . . . . ?
C10 C11 C12 C13 -57.6(10) . . . . ?
C10 C11 C12 C17 121.3(8) . . . . ?
C11 N2 C7 C6 -151.8(7) . . . . ?
C11 N2 C7 C8 29.2(9) . . . . ?
C11 C12 C13 C14 176.2(8) . . . . ?
C11 C12 C17 C16 -177.3(7) . . . . ?
C12 C13 C14 C15 2.6(14) . . . . ?
C13 C12 C17 C16 1.6(12) . . . . ?
C13 C14 C15 C16 -1.4(14) . . . . ?
C14 C15 C16 Br1 179.2(7) . . . . ?
C14 C15 C16 C17 0.3(13) . . . . ?
C15 C16 C17 C12 -0.4(12) . . . . ?
C17 C12 C13 C14 -2.7(13) . . . . ?
C18 O1 C19 C20 -164.7(7) . . . . ?
C18 N3 C9 C8 160.9(7) . . . . ?
C18 N3 C9 C10 -74.9(8) . . . . ?
C19 O1 C18 O2 2.8(11) . . . . ?
C19 O1 C18 N3 -177.6(6) . . . . ?
C19 C20 C21 C22 177.9(8) . . . . ?
C19 C20 C25 C24 -178.8(8) . . . . ?
C20 C21 C22 C23 0.8(14) . . . . ?
C21 C20 C25 C24 -0.6(12) . . . . ?
C21 C22 C23 C24 -0.1(13) . . . . ?
C22 C23 C24 C25 -0.9(13) . . . . ?
C23 C24 C25 C20 1.3(13) . . . . ?
C25 C20 C21 C22 -0.5(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.900
_oxdiff_exptl_absorpt_empirical_full_min 0.553
