# Supplementary Information (SI) for Chemical Science.
# 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. 
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data_cu_2024051101_0m
_database_code_depnum_ccdc_archive 'CCDC 2375376'
loop_
_audit_author_name
_audit_author_address
'Jian-Jun Feng'
;Hunan University
China
;
_audit_update_record             
;
2024-08-02 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;
_audit_creation_date             2024-05-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(4-benzoyl-11-bromo-3-phenyl-3,4-dihydro-2H-1,3-methanopyridazino[6,1-a]isoquinolin-1(11bH)-yl)(1-methyl-1H-imidazol-2-yl)methanone
_chemical_formula_moiety         'C31 H26 Br N4 O2'
_chemical_formula_sum            'C31 H25 Br N4 O2'
_chemical_formula_weight         565.46
_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      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                   9.8157(2)
_cell_length_b                   11.2682(3)
_cell_length_c                   14.0489(4)
_cell_angle_alpha                102.9960(10)
_cell_angle_beta                 101.6570(10)
_cell_angle_gamma                114.4520(10)
_cell_volume                     1299.74(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8009
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      68.118
_cell_measurement_theta_min      2.331
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.735
_exptl_absorpt_coefficient_mu    2.447
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_correction_T_min  0.0735
_exptl_absorpt_correction_type   multi-scan
_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    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.047
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            47937
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.224
_diffrn_reflns_theta_min         3.424
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APX-II'
_diffrn_measurement_method       ?
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4670
_reflns_number_total             4746
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.350
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4746
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.053
_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)+(0.0248P)²+1.0267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0626
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C2(H2), C16(H16), C3(H3), C14(H14), C12(H12), C15(H15), C4(H4A),
 C27(H27), C21(H21), C20(H20), C31(H31), C28(H28), C5(H5), C29(H29), C6(H6),
 C13(H13), C30(H30)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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 0.38258(2) 0.70083(2) 0.93442(2) 0.02535(7) Uani 1 1 d . . . . .
O1 O 0.57224(13) 0.22744(11) 0.84236(8) 0.0201(2) Uani 1 1 d . . . . .
O2 O 0.78462(14) 0.81673(11) 0.94551(9) 0.0259(3) Uani 1 1 d . . . . .
N1 N 0.40783(14) 0.36999(12) 0.69249(9) 0.0153(2) Uani 1 1 d . . . . .
N2 N 0.51816(14) 0.32434(12) 0.72486(10) 0.0150(2) Uani 1 1 d . . . . .
N3 N 0.70748(16) 0.96877(13) 0.82314(11) 0.0214(3) Uani 1 1 d . . . . .
N4 N 0.60784(15) 0.77791(13) 0.68525(10) 0.0203(3) Uani 1 1 d . . . . .
H4 H 0.576052 0.692493 0.645552 0.024 Uiso 1 1 calc R U . . .
C1 C 0.44770(17) 0.50410(15) 0.76848(11) 0.0145(3) Uani 1 1 d . . . . .
H1 H 0.420989 0.484093 0.830115 0.017 Uiso 1 1 calc R U . . .
C11 C 0.30090(18) 0.12674(15) 0.74247(12) 0.0173(3) Uani 1 1 d . . . . .
C8 C 0.34253(17) 0.56021(15) 0.72456(12) 0.0165(3) Uani 1 1 d . . . . .
C17 C 0.63446(17) 0.60094(15) 0.80588(11) 0.0155(3) Uani 1 1 d . . . . .
C23 C 0.71324(17) 0.53734(15) 0.87121(12) 0.0169(3) Uani 1 1 d . . . . .
H23A H 0.825883 0.601490 0.913910 0.020 Uiso 1 1 calc R U . . .
H23B H 0.651562 0.492039 0.912383 0.020 Uiso 1 1 calc R U . . .
C19 C 0.67133(18) 0.83182(15) 0.78759(12) 0.0179(3) Uani 1 1 d . . . . .
C24 C 0.69784(18) 0.55108(15) 0.72052(12) 0.0174(3) Uani 1 1 d . . . . .
H24A H 0.624493 0.515888 0.648868 0.021 Uiso 1 1 calc R U . . .
H24B H 0.806817 0.618440 0.727735 0.021 Uiso 1 1 calc R U . . .
C9 C 0.27593(18) 0.52249(16) 0.61678(12) 0.0190(3) Uani 1 1 d . . . . .
C25 C 0.68851(17) 0.43593(15) 0.76652(11) 0.0160(3) Uani 1 1 d . . . . .
C10 C 0.47305(17) 0.22995(15) 0.77614(11) 0.0157(3) Uani 1 1 d . . . . .
C2 C 0.36307(18) 0.35042(15) 0.58673(12) 0.0187(3) Uani 1 1 d . . . . .
H2 H 0.380593 0.286358 0.540989 0.022 Uiso 1 1 calc R U . . .
C18 C 0.70113(17) 0.75662(15) 0.85454(12) 0.0175(3) Uani 1 1 d . . . . .
C16 C 0.20907(19) 0.05184(16) 0.63870(13) 0.0203(3) Uani 1 1 d . . . . .
H16 H 0.252823 0.071120 0.586040 0.024 Uiso 1 1 calc R U . . .
C26 C 0.79753(18) 0.37607(15) 0.75119(13) 0.0184(3) Uani 1 1 d . . . . .
C7 C 0.31088(18) 0.65219(16) 0.78802(12) 0.0208(3) Uani 1 1 d . . . . .
C3 C 0.29660(18) 0.41891(16) 0.54823(12) 0.0208(3) Uani 1 1 d . . . . .
H3 H 0.262652 0.399769 0.475613 0.025 Uiso 1 1 calc R U . . .
C14 C -0.01108(19) -0.07812(17) 0.68917(14) 0.0255(4) Uani 1 1 d . . . . .
H14 H -0.117704 -0.148456 0.670860 0.031 Uiso 1 1 calc R U . . .
C12 C 0.23574(19) 0.09853(17) 0.81947(13) 0.0221(3) Uani 1 1 d . . . . .
H12 H 0.298317 0.148745 0.890433 0.027 Uiso 1 1 calc R U . . .
C15 C 0.05344(19) -0.05110(16) 0.61222(13) 0.0233(3) Uani 1 1 d . . . . .
H15 H -0.008957 -0.103078 0.541413 0.028 Uiso 1 1 calc R U . . .
C4 C 0.18963(19) 0.58277(18) 0.57746(14) 0.0259(4) Uani 1 1 d . . . . .
H4A H 0.146569 0.557970 0.504629 0.031 Uiso 1 1 calc R U . . .
C27 C 0.9162(2) 0.39128(17) 0.83319(14) 0.0263(4) Uani 1 1 d . . . . .
H27 H 0.927841 0.437559 0.902157 0.032 Uiso 1 1 calc R U . . .
C21 C 0.6633(2) 1.00027(17) 0.73845(14) 0.0251(3) Uani 1 1 d . . . . .
H21 H 0.672955 1.087445 0.737614 0.030 Uiso 1 1 calc R U . . .
C20 C 0.6022(2) 0.88226(17) 0.65456(13) 0.0241(3) Uani 1 1 d . . . . .
H20 H 0.561482 0.874317 0.584731 0.029 Uiso 1 1 calc R U . . .
C31 C 0.7828(2) 0.30854(18) 0.65098(14) 0.0259(4) Uani 1 1 d . . . . .
H31 H 0.701599 0.297245 0.594097 0.031 Uiso 1 1 calc R U . . .
C28 C 1.0189(2) 0.33913(18) 0.81534(16) 0.0323(4) Uani 1 1 d . . . . .
H28 H 1.099461 0.349262 0.872063 0.039 Uiso 1 1 calc R U . . .
C22 C 0.7756(2) 1.06499(18) 0.93009(14) 0.0323(4) Uani 1 1 d . . . . .
H22A H 0.714842 1.021964 0.971637 0.048 Uiso 1 1 calc R U . . .
H22B H 0.771455 1.150729 0.931430 0.048 Uiso 1 1 calc R U . . .
H22C H 0.886265 1.086712 0.958827 0.048 Uiso 1 1 calc R U . . .
C5 C 0.1658(2) 0.6783(2) 0.64315(15) 0.0325(4) Uani 1 1 d . . . . .
H5 H 0.109072 0.720412 0.615379 0.039 Uiso 1 1 calc R U . . .
C29 C 1.0034(2) 0.27295(19) 0.71534(17) 0.0329(4) Uani 1 1 d . . . . .
H29 H 1.073763 0.238136 0.703043 0.039 Uiso 1 1 calc R U . . .
C6 C 0.2244(2) 0.71236(19) 0.74876(15) 0.0295(4) Uani 1 1 d . . . . .
H6 H 0.206054 0.776026 0.794230 0.035 Uiso 1 1 calc R U . . .
C13 C 0.0791(2) -0.00323(18) 0.79206(14) 0.0268(4) Uani 1 1 d . . . . .
H13 H 0.033909 -0.021270 0.844389 0.032 Uiso 1 1 calc R U . . .
C30 C 0.8852(2) 0.2574(2) 0.63293(16) 0.0327(4) Uani 1 1 d . . . . .
H30 H 0.874109 0.211581 0.563987 0.039 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 C7 1.9012(16) . ?
O1 C10 1.2177(19) . ?
O2 C18 1.221(2) . ?
N1 N2 1.4182(17) . ?
N1 C1 1.4807(18) . ?
N1 C2 1.3993(19) . ?
N2 C25 1.5008(18) . ?
N2 C10 1.3892(19) . ?
N3 C19 1.373(2) . ?
N3 C21 1.356(2) . ?
N3 C22 1.463(2) . ?
N4 H4 0.8800 . ?
N4 C19 1.325(2) . ?
N4 C20 1.358(2) . ?
C1 H1 1.0000 . ?
C1 C8 1.518(2) . ?
C1 C17 1.589(2) . ?
C11 C10 1.495(2) . ?
C11 C16 1.391(2) . ?
C11 C12 1.395(2) . ?
C8 C9 1.408(2) . ?
C8 C7 1.389(2) . ?
C17 C23 1.556(2) . ?
C17 C24 1.558(2) . ?
C17 C18 1.517(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C25 1.549(2) . ?
C19 C18 1.463(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.553(2) . ?
C9 C3 1.449(2) . ?
C9 C4 1.393(2) . ?
C25 C26 1.507(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.333(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.388(2) . ?
C26 C27 1.384(2) . ?
C26 C31 1.388(2) . ?
C7 C6 1.393(2) . ?
C3 H3 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.388(2) . ?
C14 C13 1.379(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(2) . ?
C15 H15 0.9500 . ?
C4 H4A 0.9500 . ?
C4 C5 1.383(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.397(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.366(2) . ?
C20 H20 0.9500 . ?
C31 H31 0.9500 . ?
C31 C30 1.387(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.379(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C5 H5 0.9500 . ?
C5 C6 1.377(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.384(3) . ?
C6 H6 0.9500 . ?
C13 H13 0.9500 . ?
C30 H30 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
N2 N1 C1 111.30(11) . . ?
C2 N1 N2 114.30(12) . . ?
C2 N1 C1 119.19(12) . . ?
N1 N2 C25 114.42(11) . . ?
C10 N2 N1 115.65(11) . . ?
C10 N2 C25 116.93(12) . . ?
C19 N3 C22 128.68(14) . . ?
C21 N3 C19 106.43(14) . . ?
C21 N3 C22 124.86(14) . . ?
C19 N4 H4 127.3 . . ?
C19 N4 C20 105.48(13) . . ?
C20 N4 H4 127.3 . . ?
N1 C1 H1 106.9 . . ?
N1 C1 C8 109.91(12) . . ?
N1 C1 C17 107.99(11) . . ?
C8 C1 H1 106.9 . . ?
C8 C1 C17 117.81(12) . . ?
C17 C1 H1 106.9 . . ?
C16 C11 C10 122.42(14) . . ?
C16 C11 C12 119.79(14) . . ?
C12 C11 C10 117.59(14) . . ?
C9 C8 C1 120.64(13) . . ?
C7 C8 C1 121.92(14) . . ?
C7 C8 C9 117.43(14) . . ?
C23 C17 C1 107.65(11) . . ?
C23 C17 C24 86.64(11) . . ?
C24 C17 C1 108.39(12) . . ?
C18 C17 C1 118.46(12) . . ?
C18 C17 C23 114.28(12) . . ?
C18 C17 C24 116.79(12) . . ?
C17 C23 H23A 114.3 . . ?
C17 C23 H23B 114.3 . . ?
H23A C23 H23B 111.4 . . ?
C25 C23 C17 86.40(11) . . ?
C25 C23 H23A 114.3 . . ?
C25 C23 H23B 114.3 . . ?
N3 C19 C18 124.04(14) . . ?
N4 C19 N3 111.14(14) . . ?
N4 C19 C18 124.82(13) . . ?
C17 C24 H24A 114.3 . . ?
C17 C24 H24B 114.3 . . ?
H24A C24 H24B 111.4 . . ?
C25 C24 C17 86.17(11) . . ?
C25 C24 H24A 114.3 . . ?
C25 C24 H24B 114.3 . . ?
C8 C9 C3 118.93(14) . . ?
C4 C9 C8 120.08(15) . . ?
C4 C9 C3 120.98(15) . . ?
N2 C25 C23 107.38(11) . . ?
N2 C25 C24 106.96(11) . . ?
N2 C25 C26 111.28(12) . . ?
C23 C25 C24 87.09(11) . . ?
C26 C25 C23 123.70(13) . . ?
C26 C25 C24 117.44(12) . . ?
O1 C10 N2 120.61(13) . . ?
O1 C10 C11 121.55(13) . . ?
N2 C10 C11 117.73(13) . . ?
N1 C2 H2 119.0 . . ?
C3 C2 N1 122.00(14) . . ?
C3 C2 H2 119.0 . . ?
O2 C18 C17 120.09(14) . . ?
O2 C18 C19 121.83(14) . . ?
C19 C18 C17 117.94(13) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 C11 119.92(15) . . ?
C15 C16 H16 120.0 . . ?
C27 C26 C25 122.35(14) . . ?
C27 C26 C31 118.86(15) . . ?
C31 C26 C25 118.73(14) . . ?
C8 C7 Br1 121.12(12) . . ?
C8 C7 C6 122.43(15) . . ?
C6 C7 Br1 116.45(13) . . ?
C9 C3 H3 119.9 . . ?
C2 C3 C9 120.21(14) . . ?
C2 C3 H3 119.9 . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.23(15) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.81(15) . . ?
C13 C12 H12 120.1 . . ?
C16 C15 C14 120.03(16) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C9 C4 H4A 119.6 . . ?
C5 C4 C9 120.81(16) . . ?
C5 C4 H4A 119.6 . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.55(17) . . ?
C28 C27 H27 119.7 . . ?
N3 C21 H21 126.7 . . ?
N3 C21 C20 106.65(14) . . ?
C20 C21 H21 126.7 . . ?
N4 C20 C21 110.30(15) . . ?
N4 C20 H20 124.9 . . ?
C21 C20 H20 124.9 . . ?
C26 C31 H31 119.6 . . ?
C30 C31 C26 120.75(17) . . ?
C30 C31 H31 119.6 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 119.95(17) . . ?
C29 C28 H28 120.0 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.04(16) . . ?
C6 C5 H5 120.0 . . ?
C28 C29 H29 120.1 . . ?
C28 C29 C30 119.87(16) . . ?
C30 C29 H29 120.1 . . ?
C7 C6 H6 120.5 . . ?
C5 C6 C7 119.09(16) . . ?
C5 C6 H6 120.5 . . ?
C14 C13 C12 120.21(15) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 C31 120.01(17) . . ?
C29 C30 H30 120.0 . . ?

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 C7 C6 C5 -178.35(14) . . . . ?
N1 N2 C25 C23 69.17(14) . . . . ?
N1 N2 C25 C24 -23.12(16) . . . . ?
N1 N2 C25 C26 -152.60(12) . . . . ?
N1 N2 C10 O1 -149.02(13) . . . . ?
N1 N2 C10 C11 34.78(18) . . . . ?
N1 C1 C8 C9 -25.56(18) . . . . ?
N1 C1 C8 C7 155.85(13) . . . . ?
N1 C1 C17 C23 -68.57(14) . . . . ?
N1 C1 C17 C24 23.78(15) . . . . ?
N1 C1 C17 C18 159.88(12) . . . . ?
N1 C2 C3 C9 3.2(2) . . . . ?
N2 N1 C1 C8 171.80(11) . . . . ?
N2 N1 C1 C17 42.06(14) . . . . ?
N2 N1 C2 C3 -161.51(14) . . . . ?
N2 C25 C26 C27 -120.65(16) . . . . ?
N2 C25 C26 C31 62.22(18) . . . . ?
N3 C19 C18 O2 -12.5(2) . . . . ?
N3 C19 C18 C17 171.73(13) . . . . ?
N3 C21 C20 N4 -0.20(19) . . . . ?
N4 C19 C18 O2 166.76(15) . . . . ?
N4 C19 C18 C17 -9.0(2) . . . . ?
C1 N1 N2 C25 -44.02(15) . . . . ?
C1 N1 N2 C10 96.31(14) . . . . ?
C1 N1 C2 C3 -26.4(2) . . . . ?
C1 C8 C9 C3 5.9(2) . . . . ?
C1 C8 C9 C4 -175.12(14) . . . . ?
C1 C8 C7 Br1 -5.6(2) . . . . ?
C1 C8 C7 C6 175.11(15) . . . . ?
C1 C17 C23 C25 80.79(12) . . . . ?
C1 C17 C24 C25 -80.11(12) . . . . ?
C1 C17 C18 O2 114.47(16) . . . . ?
C1 C17 C18 C19 -69.73(17) . . . . ?
C11 C16 C15 C14 0.8(2) . . . . ?
C11 C12 C13 C14 1.3(2) . . . . ?
C8 C1 C17 C23 166.26(12) . . . . ?
C8 C1 C17 C24 -101.39(14) . . . . ?
C8 C1 C17 C18 34.70(19) . . . . ?
C8 C9 C3 C2 6.9(2) . . . . ?
C8 C9 C4 C5 -1.1(2) . . . . ?
C8 C7 C6 C5 1.0(3) . . . . ?
C17 C1 C8 C9 98.66(16) . . . . ?
C17 C1 C8 C7 -79.93(18) . . . . ?
C17 C23 C25 N2 -79.32(12) . . . . ?
C17 C23 C25 C24 27.54(10) . . . . ?
C17 C23 C25 C26 148.92(14) . . . . ?
C17 C24 C25 N2 79.78(12) . . . . ?
C17 C24 C25 C23 -27.51(10) . . . . ?
C17 C24 C25 C26 -154.35(13) . . . . ?
C23 C17 C24 C25 27.38(10) . . . . ?
C23 C17 C18 O2 -14.1(2) . . . . ?
C23 C17 C18 C19 161.74(13) . . . . ?
C23 C25 C26 C27 9.5(2) . . . . ?
C23 C25 C26 C31 -167.60(14) . . . . ?
C19 N3 C21 C20 -0.05(18) . . . . ?
C19 N4 C20 C21 0.37(18) . . . . ?
C24 C17 C23 C25 -27.46(10) . . . . ?
C24 C17 C18 O2 -113.02(16) . . . . ?
C24 C17 C18 C19 62.78(18) . . . . ?
C24 C25 C26 C27 115.64(17) . . . . ?
C24 C25 C26 C31 -61.49(19) . . . . ?
C9 C8 C7 Br1 175.75(11) . . . . ?
C9 C8 C7 C6 -3.5(2) . . . . ?
C9 C4 C5 C6 -1.6(3) . . . . ?
C25 N2 C10 O1 -9.7(2) . . . . ?
C25 N2 C10 C11 174.10(12) . . . . ?
C25 C26 C27 C28 -177.34(15) . . . . ?
C25 C26 C31 C30 177.06(15) . . . . ?
C10 N2 C25 C23 -70.64(15) . . . . ?
C10 N2 C25 C24 -162.92(12) . . . . ?
C10 N2 C25 C26 67.60(16) . . . . ?
C10 C11 C16 C15 174.50(14) . . . . ?
C10 C11 C12 C13 -175.75(14) . . . . ?
C2 N1 N2 C25 94.60(14) . . . . ?
C2 N1 N2 C10 -125.06(13) . . . . ?
C2 N1 C1 C8 35.44(17) . . . . ?
C2 N1 C1 C17 -94.30(14) . . . . ?
C18 C17 C23 C25 -145.42(12) . . . . ?
C18 C17 C24 C25 142.96(13) . . . . ?
C16 C11 C10 O1 -129.89(16) . . . . ?
C16 C11 C10 N2 46.3(2) . . . . ?
C16 C11 C12 C13 -0.6(2) . . . . ?
C26 C27 C28 C29 0.6(3) . . . . ?
C26 C31 C30 C29 0.2(3) . . . . ?
C7 C8 C9 C3 -175.46(14) . . . . ?
C7 C8 C9 C4 3.5(2) . . . . ?
C3 C9 C4 C5 177.90(16) . . . . ?
C12 C11 C10 O1 45.1(2) . . . . ?
C12 C11 C10 N2 -138.75(14) . . . . ?
C12 C11 C16 C15 -0.4(2) . . . . ?
C15 C14 C13 C12 -0.9(3) . . . . ?
C4 C9 C3 C2 -172.06(15) . . . . ?
C4 C5 C6 C7 1.7(3) . . . . ?
C27 C26 C31 C30 -0.2(2) . . . . ?
C27 C28 C29 C30 -0.5(3) . . . . ?
C21 N3 C19 N4 0.29(17) . . . . ?
C21 N3 C19 C18 179.67(14) . . . . ?
C20 N4 C19 N3 -0.40(17) . . . . ?
C20 N4 C19 C18 -179.78(14) . . . . ?
C31 C26 C27 C28 -0.2(2) . . . . ?
C28 C29 C30 C31 0.2(3) . . . . ?
C22 N3 C19 N4 178.63(16) . . . . ?
C22 N3 C19 C18 -2.0(3) . . . . ?
C22 N3 C21 C20 -178.47(15) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?

_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_exp_4382_auto
_database_code_depnum_ccdc_archive 'CCDC 2375377'
loop_
_audit_author_name
_audit_author_address
'Jian-Jun Feng'
;Hunan University
China
;
_audit_update_record             
;
2024-08-02 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;
_audit_creation_date             2024-07-22
_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        
(R)-(9-bromo-1-(1-methyl-1H-imidazole-2-carbonyl)-3-phenyl-1,2,3,11b-tetrahydro-4H-1,3-methanopyridazino[6,1-a]isoquinolin-4-yl)(4-(trifluoromethyl)phenyl)methanone
_chemical_formula_moiety         'C32 H24 Br F3 N4 O2'
_chemical_formula_sum            'C32 H24 Br F3 N4 O2'
_chemical_formula_weight         633.46
_chemical_absolute_configuration unk
_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'
F F 0.0727 0.0534 '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                   10.8729(2)
_cell_length_b                   12.87720(10)
_cell_length_c                   10.9786(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.161(2)
_cell_angle_gamma                90
_cell_volume                     1423.59(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    23677
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      73.6500
_cell_measurement_theta_min      3.3690
_shelx_estimated_absorpt_T_max   0.614
_shelx_estimated_absorpt_T_min   0.507
_exptl_absorpt_coefficient_mu    2.457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            32191
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.348
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      172.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  20.00   1.00    1.00    --    0.00  57.00  90.00   47
  2  ω     39.00  85.00   1.00    1.00    --    0.00  57.00  90.00   46
  3  ω    -27.00   8.00   1.00    1.00    --    0.00  57.00  30.00   35
  4  ω     31.00  82.00   1.00    1.00    --    0.00  57.00  30.00   51
  5  ω    -66.00 -15.00   1.00    1.00    --    0.00 -57.00  60.00   51
  6  ω    -24.00  25.00   1.00    1.00    --    0.00  77.00  30.00   49
  7  ω    -25.00  75.00   1.00    1.00    --    0.00  57.00 -90.00  100
  8  ω     -1.00  37.00   1.00    1.00    --    0.00  37.00  90.00   38
  9  ω    -27.00  83.00   1.00    1.00    --    0.00  37.00-150.00  110
 10  ω     -9.00  24.00   1.00    1.00    --    0.00 -57.00  60.00   33
 11  ω     63.00  94.00   1.00    1.00    --   92.10  64.00 -48.36   31
 12  ω     45.00 108.00   1.00    1.00    --   92.10 -82.00 -60.00   63
 13  ω      4.00  29.00   1.00    1.00    --   92.10 -82.00 120.00   25
 14  ω     48.00 127.00   1.00    1.00    --   92.10 -82.00 120.00   79
 15  ω     59.00  85.00   1.00    1.00    --   92.10  79.00 136.91   26
 16  ω    134.00 162.00   1.00    1.00    --   92.10  63.00 133.20   28
 17  ω     66.00 118.00   1.00    1.00    --   92.10  50.00 -84.46   52
 18  ω    112.00 179.00   1.00    1.00    --   92.10  79.00 -11.05   67
 19  ω     57.00  90.00   1.00    1.00    --   92.10  82.00  30.00   33
 20  ω    141.00 167.00   1.00    1.00    --   92.10  77.00 -90.00   26
 21  ω     58.00  84.00   1.00    1.00    --   92.10  82.00-150.00   26
 22  ω    116.00 142.00   1.00    1.00    --   92.10  82.00-150.00   26
 23  ω     59.00  91.00   1.00    1.00    --   92.10  77.00  60.00   32
 24  ω     57.00  82.00   1.00    1.00    --   92.10  82.00-120.00   25
 25  ω     57.00 100.00   1.00    1.00    --   92.10  82.00   0.00   43
 26  ω    107.00 180.00   1.00    1.00    --   92.10  82.00   0.00   73
 27  ω     59.00  84.00   1.00    1.00    --   92.10  77.00 -60.00   25
 28  ω    103.00 129.00   1.00    1.00    --   92.10  77.00 -60.00   26
 29  ω      7.00  53.00   1.00    1.00    --   92.10 -61.00 -90.00   46
 30  ω     73.00 111.00   1.00    1.00    --   92.10 -61.00 -90.00   38
 31  ω     58.00  98.00   1.00    1.00    --   92.10  79.00 -11.05   40
 32  ω     64.00  92.00   1.00    1.00    --   92.10  63.00 133.20   28
 33  ω     59.00  98.00   1.00    1.00    --   92.10  77.00 -90.00   39
 34  ω      4.00 119.00   1.00    1.00    --   92.10 -82.00  30.00  115
 35  ω     65.00  90.00   1.00    1.00    --   92.10  62.00 109.17   25
 36  ω     59.00  84.00   1.00    1.00    --   92.10  77.00 -30.00   25
 37  ω     57.00  82.00   1.00    1.00    --   92.10  82.00 120.00   25
 38  ω     57.00  83.00   1.00    1.00    --   92.10  82.00 -90.00   26
 39  ω     62.00 126.00   1.00    1.00    --   92.10  30.00 -30.00   64
 40  ω     57.00  97.00   1.00    1.00    --   92.10  82.00 150.00   40
 41  ω     66.00 131.00   1.00    1.00    --   92.10  42.00-148.03   65
 42  ω     64.00 153.00   1.00    1.00    --   92.10  61.00 150.00   89
 43  ω     57.00  83.00   1.00    1.00    --   92.10  82.00  60.00   26
 44  ω     67.00  93.00   1.00    1.00    --   92.10  45.00  60.00   26
 45  ω    120.00 159.00   1.00    1.00    --   92.10  45.00  60.00   39
 46  ω     66.00  91.00   1.00    1.00    --   92.10  58.00-156.73   25
 47  ω     59.00  84.00   1.00    1.00    --   92.10  77.00  30.00   25
 48  ω      5.00 120.00   1.00    1.00    --   92.10 -61.00  30.00  115
 49  ω     57.00  82.00   1.00    1.00    --   92.10  82.00-180.00   25
 50  ω     59.00  84.00   1.00    1.00    --   92.10  77.00-150.00   25
 51  ω     57.00  83.00   1.00    1.00    --   92.10  82.00 -60.00   26
 52  ω     57.00  82.00   1.00    1.00    --   92.10  82.00  90.00   25
 53  ω    115.00 178.00   1.00    1.00    --   92.10  64.00 -48.36   63
 54  ω    125.00 181.00   1.00    1.00    --   92.10  50.00 -84.46   56
 55  ω     64.00 182.00   1.00    1.00    --   92.10  61.00-132.12  118
 56  ω     66.00 153.00   1.00    1.00    --   92.10  45.00  90.00   87
 57  ω    156.00 181.00   1.00    1.00    --   92.10  45.00  90.00   25
 58  ω     66.00 171.00   1.00    1.00    --   92.10  45.00 120.00  105
 59  ω      5.00  76.00   1.00    1.00    --   92.10 -82.00-180.00   71
 60  ω     93.00 128.00   1.00    1.00    --   92.10 -82.00-180.00   35
 61  ω     38.00 100.00   1.00    1.00    --   92.10 -82.00 -90.00   62
 62  ω     67.00 117.00   1.00    1.00    --   92.10  46.00   2.55   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0480203000
_diffrn_orient_matrix_UB_12      -0.0679709000
_diffrn_orient_matrix_UB_13      0.0887254000
_diffrn_orient_matrix_UB_21      -0.0097318000
_diffrn_orient_matrix_UB_22      0.0971266000
_diffrn_orient_matrix_UB_23      0.0778621000
_diffrn_orient_matrix_UB_31      -0.1450008000
_diffrn_orient_matrix_UB_32      0.0160372000
_diffrn_orient_matrix_UB_33      -0.0948784000
_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              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.904
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4895
_reflns_number_total             5058
_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 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_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         0.209
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 2207 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.032(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5058
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.088
_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)+(0.0533P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C10(H10), C11(H11), C13(H13), C15(H15), C16(H16), C20(H20),
 C21(H21), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_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 0.01236(4) 0.73147(4) 0.79798(4) 0.05191(16) Uani 1 1 d . . . . .
F1 F -0.0226(3) 0.3962(2) -0.2176(2) 0.0502(7) Uani 1 1 d . . . . .
F2 F -0.0392(3) 0.26175(17) -0.1119(2) 0.0484(6) Uani 1 1 d . . . . .
F3 F -0.1312(2) 0.4037(2) -0.0907(3) 0.0558(7) Uani 1 1 d . . . . .
O1 O 0.6125(3) 0.62595(18) 0.8743(2) 0.0410(7) Uani 1 1 d . . . . .
O2 O 0.5682(2) 0.43237(18) 0.3152(2) 0.0284(5) Uani 1 1 d . . . . .
N1 N 0.3832(3) 0.58869(18) 0.4392(2) 0.0196(5) Uani 1 1 d . . . . .
N2 N 0.4898(3) 0.56452(19) 0.3995(2) 0.0203(5) Uani 1 1 d . . . . .
N3 N 0.5373(3) 0.3594(2) 0.7942(3) 0.0320(7) Uani 1 1 d . . . . .
N4 N 0.6261(3) 0.4266(2) 0.9957(3) 0.0292(6) Uani 1 1 d . . . . .
C1 C 0.5841(3) 0.4449(2) 0.8635(3) 0.0248(7) Uani 1 1 d . . . . .
C2 C 0.5501(4) 0.2845(3) 0.8844(4) 0.0404(9) Uani 1 1 d . . . . .
H2 H 0.524780 0.214094 0.863933 0.049 Uiso 1 1 calc R U . . .
C3 C 0.6043(4) 0.3236(3) 1.0085(4) 0.0377(8) Uani 1 1 d . . . . .
H3 H 0.623289 0.286504 1.088252 0.045 Uiso 1 1 calc R U . . .
C4 C 0.5843(3) 0.5481(2) 0.8063(3) 0.0258(7) Uani 1 1 d . . . . .
C5 C 0.5533(3) 0.5546(2) 0.6601(3) 0.0222(6) Uani 1 1 d . . . . .
C6 C 0.6371(3) 0.4848(2) 0.6048(3) 0.0229(6) Uani 1 1 d . . . . .
H6A H 0.728770 0.471477 0.667533 0.027 Uiso 1 1 calc R U . . .
H6B H 0.592340 0.419831 0.562773 0.027 Uiso 1 1 calc R U . . .
C7 C 0.6247(3) 0.5753(2) 0.5070(3) 0.0210(6) Uani 1 1 d . . . . .
C8 C 0.4029(3) 0.5426(2) 0.5691(3) 0.0210(6) Uani 1 1 d . . . . .
H8 H 0.383253 0.466678 0.555618 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3060(3) 0.5890(2) 0.6234(3) 0.0238(7) Uani 1 1 d . . . . .
C10 C 0.2742(4) 0.5358(3) 0.7175(3) 0.0308(7) Uani 1 1 d . . . . .
H10 H 0.312018 0.469217 0.745511 0.037 Uiso 1 1 calc R U . . .
C11 C 0.1887(4) 0.5774(3) 0.7719(4) 0.0362(8) Uani 1 1 d . . . . .
H11 H 0.167979 0.540239 0.836486 0.043 Uiso 1 1 calc R U . . .
C12 C 0.1344(4) 0.6741(3) 0.7297(4) 0.0337(8) Uani 1 1 d . . . . .
C13 C 0.1632(3) 0.7292(3) 0.6368(3) 0.0311(7) Uani 1 1 d . . . . .
H13 H 0.124961 0.795784 0.610110 0.037 Uiso 1 1 calc R U . . .
C14 C 0.2485(3) 0.6874(2) 0.5818(3) 0.0248(7) Uani 1 1 d . . . . .
C15 C 0.2737(3) 0.7398(2) 0.4768(3) 0.0268(6) Uani 1 1 d . . . . .
H15 H 0.241912 0.808456 0.452407 0.032 Uiso 1 1 calc R U . . .
C16 C 0.3414(3) 0.6920(2) 0.4146(3) 0.0225(6) Uani 1 1 d . . . . .
H16 H 0.362261 0.729686 0.350549 0.027 Uiso 1 1 calc R U . . .
C17 C 0.6116(3) 0.6496(2) 0.6132(3) 0.0227(6) Uani 1 1 d . . . . .
H17A H 0.697389 0.674771 0.677981 0.027 Uiso 1 1 calc R U . . .
H17B H 0.548064 0.707338 0.577488 0.027 Uiso 1 1 calc R U . . .
C18 C 0.4721(3) 0.4823(2) 0.3124(3) 0.0214(6) Uani 1 1 d . . . . .
C19 C 0.3368(3) 0.4584(2) 0.2113(3) 0.0216(6) Uani 1 1 d . . . . .
C20 C 0.2292(4) 0.5260(2) 0.1644(3) 0.0300(7) Uani 1 1 d . . . . .
H20 H 0.235738 0.593566 0.200955 0.036 Uiso 1 1 calc R U . . .
C21 C 0.1124(3) 0.4950(3) 0.0645(3) 0.0298(7) Uani 1 1 d . . . . .
H21 H 0.039272 0.541466 0.033055 0.036 Uiso 1 1 calc R U . . .
C22 C 0.1020(3) 0.3963(3) 0.0103(3) 0.0252(7) Uani 1 1 d . . . . .
C23 C 0.2093(4) 0.3289(3) 0.0555(3) 0.0295(7) Uani 1 1 d . . . . .
H23 H 0.203009 0.261611 0.018197 0.035 Uiso 1 1 calc R U . . .
C24 C 0.3250(3) 0.3599(2) 0.1547(3) 0.0255(7) Uani 1 1 d . . . . .
H24 H 0.398203 0.313456 0.185226 0.031 Uiso 1 1 calc R U . . .
C25 C 0.7303(3) 0.6003(2) 0.4534(3) 0.0230(6) Uani 1 1 d . . . . .
C26 C 0.7201(4) 0.6918(3) 0.3836(3) 0.0334(8) Uani 1 1 d . . . . .
H26 H 0.647360 0.737377 0.369921 0.040 Uiso 1 1 calc R U . . .
C27 C 0.8168(4) 0.7168(3) 0.3334(4) 0.0393(8) Uani 1 1 d . . . . .
H27 H 0.809189 0.779135 0.284855 0.047 Uiso 1 1 calc R U . . .
C28 C 0.9229(4) 0.6518(3) 0.3536(4) 0.0385(9) Uani 1 1 d . . . . .
H28 H 0.987885 0.668798 0.318462 0.046 Uiso 1 1 calc R U . . .
C29 C 0.9348(4) 0.5613(3) 0.4256(4) 0.0348(8) Uani 1 1 d . . . . .
H29 H 1.008631 0.516623 0.440711 0.042 Uiso 1 1 calc R U . . .
C30 C 0.8395(4) 0.5361(3) 0.4753(3) 0.0289(7) Uani 1 1 d . . . . .
H30 H 0.848579 0.474148 0.525013 0.035 Uiso 1 1 calc R U . . .
C31 C -0.0226(4) 0.3648(3) -0.1005(3) 0.0317(8) Uani 1 1 d . . . . .
C32 C 0.6932(5) 0.4964(4) 1.1041(4) 0.0529(12) Uani 1 1 d . . . . .
H32A H 0.780388 0.514894 1.103329 0.079 Uiso 1 1 calc R U . . .
H32B H 0.704778 0.462091 1.187346 0.079 Uiso 1 1 calc R U . . .
H32C H 0.639970 0.559460 1.094786 0.079 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 C12 1.903(4) . ?
F1 C31 1.347(4) . ?
F2 C31 1.339(4) . ?
F3 C31 1.324(5) . ?
O1 C4 1.218(4) . ?
O2 C18 1.217(4) . ?
N1 N2 1.418(4) . ?
N1 C8 1.484(4) . ?
N1 C16 1.399(4) . ?
N2 C7 1.502(4) . ?
N2 C18 1.391(4) . ?
N3 C1 1.326(4) . ?
N3 C2 1.351(5) . ?
N4 C1 1.369(4) . ?
N4 C3 1.363(5) . ?
N4 C32 1.449(5) . ?
C1 C4 1.469(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.360(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.514(4) . ?
C5 C6 1.556(4) . ?
C5 C8 1.570(4) . ?
C5 C17 1.553(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.556(4) . ?
C7 C17 1.556(4) . ?
C7 C25 1.509(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.514(4) . ?
C9 C10 1.388(5) . ?
C9 C14 1.410(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(6) . ?
C12 C13 1.371(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.393(5) . ?
C14 C15 1.449(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.328(4) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.503(4) . ?
C19 C20 1.392(5) . ?
C19 C24 1.397(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(5) . ?
C22 C23 1.387(5) . ?
C22 C31 1.495(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.376(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(5) . ?
C25 C30 1.392(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.397(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.373(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.386(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.379(5) . ?
C30 H30 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

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
N2 N1 C8 111.7(2) . . ?
C16 N1 N2 113.2(2) . . ?
C16 N1 C8 118.9(2) . . ?
N1 N2 C7 114.1(2) . . ?
C18 N2 N1 117.4(3) . . ?
C18 N2 C7 116.9(2) . . ?
C1 N3 C2 105.1(3) . . ?
C1 N4 C32 128.8(3) . . ?
C3 N4 C1 106.0(3) . . ?
C3 N4 C32 124.9(3) . . ?
N3 C1 N4 111.6(3) . . ?
N3 C1 C4 124.6(3) . . ?
N4 C1 C4 123.7(3) . . ?
N3 C2 H2 124.6 . . ?
N3 C2 C3 110.8(3) . . ?
C3 C2 H2 124.6 . . ?
N4 C3 H3 126.8 . . ?
C2 C3 N4 106.5(3) . . ?
C2 C3 H3 126.8 . . ?
O1 C4 C1 121.6(3) . . ?
O1 C4 C5 120.5(3) . . ?
C1 C4 C5 117.8(3) . . ?
C4 C5 C6 117.0(3) . . ?
C4 C5 C8 115.5(3) . . ?
C4 C5 C17 116.1(3) . . ?
C6 C5 C8 108.5(2) . . ?
C17 C5 C6 87.3(2) . . ?
C17 C5 C8 108.9(2) . . ?
C5 C6 H6A 114.4 . . ?
C5 C6 H6B 114.4 . . ?
H6A C6 H6B 111.5 . . ?
C7 C6 C5 85.8(2) . . ?
C7 C6 H6A 114.4 . . ?
C7 C6 H6B 114.4 . . ?
N2 C7 C6 106.1(2) . . ?
N2 C7 C17 107.9(2) . . ?
N2 C7 C25 112.0(2) . . ?
C17 C7 C6 87.2(2) . . ?
C25 C7 C6 123.2(3) . . ?
C25 C7 C17 117.4(2) . . ?
N1 C8 C5 108.0(2) . . ?
N1 C8 H8 107.6 . . ?
N1 C8 C9 110.6(2) . . ?
C5 C8 H8 107.6 . . ?
C9 C8 C5 115.1(2) . . ?
C9 C8 H8 107.6 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 C14 118.7(3) . . ?
C14 C9 C8 121.0(3) . . ?
C9 C10 H10 119.2 . . ?
C9 C10 C11 121.7(3) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.3(3) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 Br1 119.4(3) . . ?
C13 C12 Br1 118.7(3) . . ?
C13 C12 C11 121.9(3) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.9(4) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 C15 118.9(3) . . ?
C13 C14 C9 119.6(3) . . ?
C13 C14 C15 121.5(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
N1 C16 H16 118.5 . . ?
C15 C16 N1 123.0(3) . . ?
C15 C16 H16 118.5 . . ?
C5 C17 C7 85.9(2) . . ?
C5 C17 H17A 114.3 . . ?
C5 C17 H17B 114.3 . . ?
C7 C17 H17A 114.3 . . ?
C7 C17 H17B 114.3 . . ?
H17A C17 H17B 111.5 . . ?
O2 C18 N2 119.3(3) . . ?
O2 C18 C19 120.2(3) . . ?
N2 C18 C19 120.5(3) . . ?
C20 C19 C18 126.7(3) . . ?
C20 C19 C24 118.6(3) . . ?
C24 C19 C18 114.5(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.3(3) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C31 119.9(3) . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 C31 120.2(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.7(3) . . ?
C24 C23 H23 120.1 . . ?
C19 C24 H24 119.4 . . ?
C23 C24 C19 121.3(3) . . ?
C23 C24 H24 119.4 . . ?
C26 C25 C7 118.8(3) . . ?
C26 C25 C30 119.1(3) . . ?
C30 C25 C7 122.1(3) . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.9(3) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.5(3) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 120.1 . . ?
C27 C28 C29 119.8(3) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.1(4) . . ?
C30 C29 H29 120.0 . . ?
C25 C30 H30 119.6 . . ?
C29 C30 C25 120.7(3) . . ?
C29 C30 H30 119.6 . . ?
F1 C31 C22 111.7(3) . . ?
F2 C31 F1 104.9(3) . . ?
F2 C31 C22 113.2(3) . . ?
F3 C31 F1 106.5(3) . . ?
F3 C31 F2 106.8(3) . . ?
F3 C31 C22 113.2(3) . . ?
N4 C32 H32A 109.5 . . ?
N4 C32 H32B 109.5 . . ?
N4 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C12 C13 C14 -177.7(2) . . . . ?
O1 C4 C5 C6 124.5(4) . . . . ?
O1 C4 C5 C8 -105.9(4) . . . . ?
O1 C4 C5 C17 23.5(5) . . . . ?
O2 C18 C19 C20 -156.0(3) . . . . ?
O2 C18 C19 C24 19.3(4) . . . . ?
N1 N2 C7 C6 70.5(3) . . . . ?
N1 N2 C7 C17 -21.8(3) . . . . ?
N1 N2 C7 C25 -152.4(2) . . . . ?
N1 N2 C18 O2 -150.9(3) . . . . ?
N1 N2 C18 C19 32.1(4) . . . . ?
N1 C8 C9 C10 158.1(3) . . . . ?
N1 C8 C9 C14 -23.3(4) . . . . ?
N2 N1 C8 C5 40.3(3) . . . . ?
N2 N1 C8 C9 167.0(2) . . . . ?
N2 N1 C16 C15 -159.1(3) . . . . ?
N2 C7 C17 C5 78.4(2) . . . . ?
N2 C7 C25 C26 61.6(4) . . . . ?
N2 C7 C25 C30 -120.4(3) . . . . ?
N2 C18 C19 C20 21.0(5) . . . . ?
N2 C18 C19 C24 -163.7(3) . . . . ?
N3 C1 C4 O1 170.3(4) . . . . ?
N3 C1 C4 C5 -12.0(5) . . . . ?
N3 C2 C3 N4 0.1(5) . . . . ?
N4 C1 C4 O1 -6.0(5) . . . . ?
N4 C1 C4 C5 171.7(3) . . . . ?
C1 N3 C2 C3 0.1(5) . . . . ?
C1 N4 C3 C2 -0.2(4) . . . . ?
C1 C4 C5 C6 -53.2(4) . . . . ?
C1 C4 C5 C8 76.4(4) . . . . ?
C1 C4 C5 C17 -154.2(3) . . . . ?
C2 N3 C1 N4 -0.2(4) . . . . ?
C2 N3 C1 C4 -176.9(3) . . . . ?
C3 N4 C1 N3 0.3(4) . . . . ?
C3 N4 C1 C4 177.0(3) . . . . ?
C4 C5 C6 C7 -145.6(3) . . . . ?
C4 C5 C8 N1 159.2(2) . . . . ?
C4 C5 C8 C9 35.1(4) . . . . ?
C4 C5 C17 C7 146.4(3) . . . . ?
C5 C6 C7 N2 -80.3(2) . . . . ?
C5 C6 C7 C17 27.5(2) . . . . ?
C5 C6 C7 C25 148.7(3) . . . . ?
C5 C8 C9 C10 -79.2(4) . . . . ?
C5 C8 C9 C14 99.4(3) . . . . ?
C6 C5 C8 N1 -67.2(3) . . . . ?
C6 C5 C8 C9 168.8(2) . . . . ?
C6 C5 C17 C7 27.6(2) . . . . ?
C6 C7 C17 C5 -27.6(2) . . . . ?
C6 C7 C25 C26 -170.0(3) . . . . ?
C6 C7 C25 C30 8.0(4) . . . . ?
C7 N2 C18 O2 -9.8(4) . . . . ?
C7 N2 C18 C19 173.2(3) . . . . ?
C7 C25 C26 C27 179.8(3) . . . . ?
C7 C25 C30 C29 -179.7(3) . . . . ?
C8 N1 N2 C7 -43.8(3) . . . . ?
C8 N1 N2 C18 98.3(3) . . . . ?
C8 N1 C16 C15 -25.0(4) . . . . ?
C8 C5 C6 C7 81.5(3) . . . . ?
C8 C5 C17 C7 -81.1(3) . . . . ?
C8 C9 C10 C11 178.2(3) . . . . ?
C8 C9 C14 C13 -177.9(3) . . . . ?
C8 C9 C14 C15 5.8(4) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C9 C14 C15 C16 5.1(5) . . . . ?
C10 C9 C14 C13 0.8(5) . . . . ?
C10 C9 C14 C15 -175.6(3) . . . . ?
C10 C11 C12 Br1 178.0(3) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C12 C13 C14 C9 -0.8(5) . . . . ?
C12 C13 C14 C15 175.5(3) . . . . ?
C13 C14 C15 C16 -171.1(3) . . . . ?
C14 C9 C10 C11 -0.5(5) . . . . ?
C14 C15 C16 N1 4.5(5) . . . . ?
C16 N1 N2 C7 93.6(3) . . . . ?
C16 N1 N2 C18 -124.3(3) . . . . ?
C16 N1 C8 C5 -94.5(3) . . . . ?
C16 N1 C8 C9 32.3(4) . . . . ?
C17 C5 C6 C7 -27.6(2) . . . . ?
C17 C5 C8 N1 26.4(3) . . . . ?
C17 C5 C8 C9 -97.6(3) . . . . ?
C17 C7 C25 C26 -64.1(4) . . . . ?
C17 C7 C25 C30 113.9(3) . . . . ?
C18 N2 C7 C6 -71.8(3) . . . . ?
C18 N2 C7 C17 -164.1(2) . . . . ?
C18 N2 C7 C25 65.2(3) . . . . ?
C18 C19 C20 C21 175.9(3) . . . . ?
C18 C19 C24 C23 -176.4(3) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C20 C19 C24 C23 -0.8(5) . . . . ?
C20 C21 C22 C23 -0.6(5) . . . . ?
C20 C21 C22 C31 -177.9(3) . . . . ?
C21 C22 C23 C24 0.6(5) . . . . ?
C21 C22 C31 F1 84.3(4) . . . . ?
C21 C22 C31 F2 -157.6(3) . . . . ?
C21 C22 C31 F3 -35.9(5) . . . . ?
C22 C23 C24 C19 0.1(5) . . . . ?
C23 C22 C31 F1 -92.9(4) . . . . ?
C23 C22 C31 F2 25.2(5) . . . . ?
C23 C22 C31 F3 146.9(3) . . . . ?
C24 C19 C20 C21 0.8(5) . . . . ?
C25 C7 C17 C5 -153.9(3) . . . . ?
C25 C26 C27 C28 -0.6(6) . . . . ?
C26 C25 C30 C29 -1.7(5) . . . . ?
C26 C27 C28 C29 -0.7(6) . . . . ?
C27 C28 C29 C30 0.8(6) . . . . ?
C28 C29 C30 C25 0.4(5) . . . . ?
C30 C25 C26 C27 1.7(5) . . . . ?
C31 C22 C23 C24 177.9(3) . . . . ?
C32 N4 C1 N3 174.2(4) . . . . ?
C32 N4 C1 C4 -9.0(6) . . . . ?
C32 N4 C3 C2 -174.5(4) . . . . ?

_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 4.223
_oxdiff_exptl_absorpt_empirical_full_min 0.423
