# 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 
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data_20201107lin_abcz2728_cf_0m_5
_database_code_depnum_ccdc_archive 'CCDC 2215400'
loop_
_audit_author_name
_audit_author_address
'Junling Zhao'
;Sun Yatsen University
China
;
_audit_update_record             
;
2022-10-26 deposited with the CCDC.	2022-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-11-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        3ab
_chemical_formula_moiety         'C29 H26 Br N3 O4'
_chemical_formula_sum            'C29 H26 Br N3 O4'
_chemical_formula_weight         560.44
_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 0.0148 0.0070 '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 -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   12.1958(14)
_cell_length_b                   7.8993(9)
_cell_length_c                   13.8896(15)
_cell_angle_alpha                90
_cell_angle_beta                 104.960(5)
_cell_angle_gamma                90
_cell_volume                     1292.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3271
_cell_measurement_temperature    192.98
_cell_measurement_theta_max      58.194
_cell_measurement_theta_min      3.263
_shelx_estimated_absorpt_T_max   0.848
_shelx_estimated_absorpt_T_min   0.822
_exptl_absorpt_coefficient_mu    1.700
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 17862 reflections, Rint = 0.0636
 (10138 with I > 3sig(I), Rint = 0.0545)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3055
_diffrn_reflns_point_group_measured_fraction_full 0.526
_diffrn_reflns_point_group_measured_fraction_max 0.512
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.808
_diffrn_reflns_theta_min         2.865
_diffrn_ambient_temperature      192.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                2208
_reflns_number_total             3055
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         3055
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.065
_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)+(0.0359P)²+1.0723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1263
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.614(2)
 0.386(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C19A-C18 \\sim C19B-C18
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C19A \\sim C19B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
5. Others
 Sof(H18C)=Sof(H18D)=Sof(C19B)=Sof(H19A)=Sof(H19B)=Sof(H19C)=1-FVAR(1)
 Sof(H18A)=Sof(H18B)=Sof(C19A)=Sof(H19D)=Sof(H19E)=Sof(H19F)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C18(H18C,H18D), C18(H18A,H18B)
6.b Aromatic/amide H refined with riding coordinates:
 N006(H006), N009(H009), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10),
 C14(H14), C15(H15), C20(H20), C26(H26), C27(H27), C28(H28), C29(H29)
6.c Idealised Me refined as rotating group:
 C19B(H19A,H19B,H19C), C23(H23A,H23B,H23C), C19A(H19D,H19E,H19F)
6.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.08325(7) 1.07920(14) -0.06664(6) 0.0698(3) Uani 1 1 d . . . . .
O002 O 0.5946(4) 0.9088(6) 0.5205(4) 0.0459(12) Uani 1 1 d . . . . .
O003 O 0.6174(4) 0.2888(6) 0.4837(3) 0.0397(11) Uani 1 1 d . . . . .
H003 H 0.556316 0.321209 0.495102 0.060 Uiso 1 1 calc R U . . .
O004 O 0.7809(4) 0.1846(7) 0.4179(4) 0.0535(13) Uani 1 1 d . . . . .
O007 O 0.8320(4) 0.4476(7) 0.3863(4) 0.0582(14) Uani 1 1 d . . . . .
N005 N 0.7435(5) 0.8516(8) 0.6556(4) 0.0432(13) Uani 1 1 d . . . . .
N006 N 0.5071(4) 0.0733(9) 0.3295(3) 0.0419(11) Uani 1 1 d . . . . .
H006 H 0.544533 0.054040 0.391717 0.050 Uiso 1 1 calc R U . . .
N009 N 0.3600(5) 0.3003(9) 0.0144(4) 0.0564(17) Uani 1 1 d . . . . .
H009 H 0.319721 0.206561 0.003823 0.068 Uiso 1 1 calc R U . . .
C1 C 0.1643(6) 0.8767(11) -0.0670(5) 0.055(2) Uani 1 1 d . . . . .
C2 C 0.2157(7) 0.8459(12) -0.1414(6) 0.063(2) Uani 1 1 d . . . . .
H2 H 0.210595 0.924951 -0.193922 0.076 Uiso 1 1 calc R U . . .
C3 C 0.2763(6) 0.6952(12) -0.1383(5) 0.057(2) Uani 1 1 d . . . . .
H3 H 0.314238 0.674087 -0.188870 0.069 Uiso 1 1 calc R U . . .
C4 C 0.2830(5) 0.5771(15) -0.0652(4) 0.0476(14) Uani 1 1 d . . . . .
C5 C 0.2266(6) 0.6101(12) 0.0075(5) 0.052(2) Uani 1 1 d . . . . .
H5 H 0.228126 0.528172 0.057925 0.063 Uiso 1 1 calc R U . . .
C6 C 0.1684(6) 0.7591(11) 0.0083(5) 0.054(2) Uani 1 1 d . . . . .
H6 H 0.131607 0.781240 0.059453 0.065 Uiso 1 1 calc R U . . .
C7 C 0.3509(7) 0.4169(11) -0.0672(5) 0.058(2) Uani 1 1 d . . . . .
H7A H 0.316296 0.355981 -0.129963 0.070 Uiso 1 1 calc R U . . .
H7B H 0.428573 0.450062 -0.069180 0.070 Uiso 1 1 calc R U . . .
C8 C 0.4304(5) 0.3301(10) 0.1100(4) 0.0413(15) Uani 1 1 d . . . . .
C9 C 0.4882(6) 0.4784(10) 0.1378(5) 0.0448(16) Uani 1 1 d . . . . .
H9 H 0.482761 0.567339 0.090747 0.054 Uiso 1 1 calc R U . . .
C10 C 0.5564(6) 0.4994(9) 0.2368(5) 0.0432(15) Uani 1 1 d . . . . .
H10 H 0.595551 0.603414 0.254359 0.052 Uiso 1 1 calc R U . . .
C11 C 0.5680(5) 0.3750(8) 0.3085(4) 0.0371(14) Uani 1 1 d . . . . .
C12 C 0.5095(5) 0.2235(9) 0.2786(4) 0.0377(14) Uani 1 1 d . . . . .
C13 C 0.4398(6) 0.1973(10) 0.1811(5) 0.0437(16) Uani 1 1 d . . . . .
C14 C 0.3956(6) 0.0317(9) 0.1775(5) 0.0452(18) Uani 1 1 d . . . . .
H14 H 0.345192 -0.020310 0.121620 0.054 Uiso 1 1 calc R U . . .
C15 C 0.4381(6) -0.0400(10) 0.2686(5) 0.0504(18) Uani 1 1 d . . . . .
H15 H 0.422190 -0.151428 0.286922 0.061 Uiso 1 1 calc R U . . .
C16 C 0.6468(5) 0.3996(8) 0.4141(4) 0.0356(13) Uani 1 1 d . . . . .
C17 C 0.7649(6) 0.3486(10) 0.4053(5) 0.0449(16) Uani 1 1 d . . . . .
C18 C 0.8884(6) 0.1133(12) 0.4082(7) 0.063(2) Uani 1 1 d D . . . .
H18C H 0.950465 0.134753 0.468748 0.076 Uiso 0.45(8) 1 calc R U P A 2
H18D H 0.909809 0.160761 0.349607 0.076 Uiso 0.45(8) 1 calc R U P A 2
H18A H 0.953408 0.174835 0.451505 0.076 Uiso 0.55(8) 1 calc R U P A 1
H18B H 0.893610 0.121337 0.338368 0.076 Uiso 0.55(8) 1 calc R U P A 1
C19B C 0.862(6) -0.074(3) 0.395(6) 0.105(10) Uani 0.45(8) 1 d D U P A 2
H19A H 0.844450 -0.118797 0.454985 0.158 Uiso 0.45(8) 1 calc R U P A 2
H19B H 0.928109 -0.133971 0.383590 0.158 Uiso 0.45(8) 1 calc R U P A 2
H19C H 0.796788 -0.090989 0.337455 0.158 Uiso 0.45(8) 1 calc R U P A 2
C20 C 0.6412(4) 0.5770(12) 0.4492(4) 0.0383(12) Uani 1 1 d . . . . .
H20 H 0.593384 0.653041 0.404288 0.046 Uiso 1 1 calc R U . . .
C21 C 0.6975(5) 0.6400(8) 0.5388(4) 0.0372(14) Uani 1 1 d . . . . .
C22 C 0.6708(6) 0.8140(9) 0.5659(5) 0.0411(15) Uani 1 1 d . . . . .
C23 C 0.7406(7) 1.0071(10) 0.7079(6) 0.059(2) Uani 1 1 d . . . . .
H23A H 0.712613 1.098069 0.659910 0.089 Uiso 1 1 calc R U . . .
H23B H 0.817296 1.034937 0.747671 0.089 Uiso 1 1 calc R U . . .
H23C H 0.690060 0.994722 0.752033 0.089 Uiso 1 1 calc R U . . .
C24 C 0.8130(5) 0.7096(10) 0.6922(5) 0.0419(16) Uani 1 1 d . . . . .
C25 C 0.7857(4) 0.5760(12) 0.6227(4) 0.0395(12) Uani 1 1 d . . . . .
C26 C 0.8408(6) 0.4257(10) 0.6450(5) 0.0467(17) Uani 1 1 d . . . . .
H26 H 0.821564 0.333044 0.600178 0.056 Uiso 1 1 calc R U . . .
C27 C 0.9257(6) 0.4072(11) 0.7338(5) 0.0536(19) Uani 1 1 d . . . . .
H27 H 0.965464 0.303103 0.748724 0.064 Uiso 1 1 calc R U . . .
C28 C 0.9516(6) 0.5421(11) 0.8000(5) 0.056(2) Uani 1 1 d . . . . .
H28 H 1.008995 0.528606 0.860388 0.067 Uiso 1 1 calc R U . . .
C29 C 0.8958(6) 0.6957(11) 0.7800(5) 0.0516(18) Uani 1 1 d . . . . .
H29 H 0.914065 0.787890 0.825229 0.062 Uiso 1 1 calc R U . . .
C19A C 0.889(5) -0.071(3) 0.440(5) 0.105(10) Uani 0.55(8) 1 d D U P A 1
H19D H 0.895686 -0.076408 0.511853 0.158 Uiso 0.55(8) 1 calc R U P A 1
H19E H 0.953320 -0.129399 0.425033 0.158 Uiso 0.55(8) 1 calc R U P A 1
H19F H 0.817992 -0.125085 0.403882 0.158 Uiso 0.55(8) 1 calc R U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.881(9) . ?
O002 C22 1.232(8) . ?
O003 H003 0.8400 . ?
O003 C16 1.418(7) . ?
O004 C17 1.314(9) . ?
O004 C18 1.465(8) . ?
O007 C17 1.210(9) . ?
N005 C22 1.363(8) . ?
N005 C23 1.432(9) . ?
N005 C24 1.419(9) . ?
N006 H006 0.8800 . ?
N006 C12 1.385(9) . ?
N006 C15 1.363(9) . ?
N009 H009 0.8800 . ?
N009 C7 1.443(9) . ?
N009 C8 1.402(7) . ?
C1 C2 1.362(10) . ?
C1 C6 1.390(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.366(12) . ?
C4 C5 1.386(9) . ?
C4 C7 1.517(13) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(12) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.370(10) . ?
C8 C13 1.425(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.421(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(9) . ?
C11 C12 1.400(9) . ?
C11 C16 1.544(8) . ?
C12 C13 1.416(8) . ?
C13 C14 1.411(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.361(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.530(9) . ?
C16 C20 1.491(11) . ?
C18 H18C 0.9900 . ?
C18 H18D 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19B 1.52(2) . ?
C18 C19A 1.52(2) . ?
C19B H19A 0.9800 . ?
C19B H19B 0.9800 . ?
C19B H19C 0.9800 . ?
C20 H20 0.9500 . ?
C20 C21 1.352(8) . ?
C21 C22 1.484(9) . ?
C21 C25 1.457(8) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.411(10) . ?
C24 C29 1.372(9) . ?
C25 C26 1.360(11) . ?
C26 H26 0.9500 . ?
C26 C27 1.398(9) . ?
C27 H27 0.9500 . ?
C27 C28 1.390(11) . ?
C28 H28 0.9500 . ?
C28 C29 1.384(11) . ?
C29 H29 0.9500 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 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
C16 O003 H003 109.5 . . ?
C17 O004 C18 118.2(6) . . ?
C22 N005 C23 123.7(7) . . ?
C22 N005 C24 110.1(6) . . ?
C24 N005 C23 125.9(6) . . ?
C12 N006 H006 125.2 . . ?
C15 N006 H006 125.2 . . ?
C15 N006 C12 109.7(5) . . ?
C7 N009 H009 118.6 . . ?
C8 N009 H009 118.6 . . ?
C8 N009 C7 122.8(6) . . ?
C2 C1 Br1 120.0(6) . . ?
C2 C1 C6 121.1(8) . . ?
C6 C1 Br1 118.9(6) . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.2(7) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.3(7) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 117.9(9) . . ?
C3 C4 C7 119.0(6) . . ?
C5 C4 C7 123.1(8) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(8) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 119.0(7) . . ?
C5 C6 H6 120.5 . . ?
N009 C7 C4 116.7(6) . . ?
N009 C7 H7A 108.1 . . ?
N009 C7 H7B 108.1 . . ?
C4 C7 H7A 108.1 . . ?
C4 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
N009 C8 C13 116.9(6) . . ?
C9 C8 N009 123.7(6) . . ?
C9 C8 C13 119.4(5) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.2(6) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 118.6 . . ?
C11 C10 C9 122.7(7) . . ?
C11 C10 H10 118.6 . . ?
C10 C11 C12 116.4(5) . . ?
C10 C11 C16 121.2(6) . . ?
C12 C11 C16 122.2(5) . . ?
N006 C12 C11 131.1(5) . . ?
N006 C12 C13 106.1(6) . . ?
C11 C12 C13 122.8(6) . . ?
C12 C13 C8 118.5(6) . . ?
C14 C13 C8 134.1(6) . . ?
C14 C13 C12 107.4(6) . . ?
C13 C14 H14 126.2 . . ?
C15 C14 C13 107.6(6) . . ?
C15 C14 H14 126.2 . . ?
N006 C15 H15 125.4 . . ?
C14 C15 N006 109.2(6) . . ?
C14 C15 H15 125.4 . . ?
O003 C16 C11 111.4(5) . . ?
O003 C16 C17 107.5(5) . . ?
O003 C16 C20 108.4(5) . . ?
C17 C16 C11 105.0(5) . . ?
C20 C16 C11 111.0(5) . . ?
C20 C16 C17 113.4(5) . . ?
O004 C17 C16 111.1(6) . . ?
O007 C17 O004 125.5(7) . . ?
O007 C17 C16 123.4(7) . . ?
O004 C18 H18C 111.2 . . ?
O004 C18 H18D 111.2 . . ?
O004 C18 H18A 110.5 . . ?
O004 C18 H18B 110.5 . . ?
O004 C18 C19B 103(3) . . ?
O004 C18 C19A 106(2) . . ?
H18C C18 H18D 109.1 . . ?
H18A C18 H18B 108.7 . . ?
C19B C18 H18C 111.2 . . ?
C19B C18 H18D 111.2 . . ?
C19A C18 H18A 110.5 . . ?
C19A C18 H18B 110.5 . . ?
C18 C19B H19A 109.5 . . ?
C18 C19B H19B 109.5 . . ?
C18 C19B H19C 109.5 . . ?
H19A C19B H19B 109.5 . . ?
H19A C19B H19C 109.5 . . ?
H19B C19B H19C 109.5 . . ?
C16 C20 H20 116.9 . . ?
C21 C20 C16 126.3(6) . . ?
C21 C20 H20 116.9 . . ?
C20 C21 C22 118.8(6) . . ?
C20 C21 C25 134.7(7) . . ?
C25 C21 C22 106.5(6) . . ?
O002 C22 N005 124.2(7) . . ?
O002 C22 C21 128.3(6) . . ?
N005 C22 C21 107.4(6) . . ?
N005 C23 H23A 109.5 . . ?
N005 C23 H23B 109.5 . . ?
N005 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 N005 109.4(5) . . ?
C29 C24 N005 128.0(7) . . ?
C29 C24 C25 122.6(7) . . ?
C24 C25 C21 106.4(7) . . ?
C26 C25 C21 134.8(7) . . ?
C26 C25 C24 118.8(5) . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.1(7) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 120.2 . . ?
C28 C27 C26 119.6(7) . . ?
C28 C27 H27 120.2 . . ?
C27 C28 H28 119.2 . . ?
C29 C28 C27 121.6(6) . . ?
C29 C28 H28 119.2 . . ?
C24 C29 C28 117.3(7) . . ?
C24 C29 H29 121.3 . . ?
C28 C29 H29 121.3 . . ?
C18 C19A H19D 109.5 . . ?
C18 C19A H19E 109.5 . . ?
C18 C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 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 C1 C2 C3 179.2(6) . . . . ?
Br1 C1 C6 C5 179.3(5) . . . . ?
O003 C16 C17 O004 32.4(7) . . . . ?
O003 C16 C17 O007 -149.7(6) . . . . ?
O003 C16 C20 C21 55.8(8) . . . . ?
N005 C24 C25 C21 1.4(7) . . . . ?
N005 C24 C25 C26 -178.2(6) . . . . ?
N005 C24 C29 C28 179.2(7) . . . . ?
N006 C12 C13 C8 -177.3(6) . . . . ?
N006 C12 C13 C14 1.3(7) . . . . ?
N009 C8 C9 C10 178.9(7) . . . . ?
N009 C8 C13 C12 -179.5(6) . . . . ?
N009 C8 C13 C14 2.4(13) . . . . ?
C1 C2 C3 C4 1.7(12) . . . . ?
C2 C1 C6 C5 0.6(11) . . . . ?
C2 C3 C4 C5 0.3(12) . . . . ?
C2 C3 C4 C7 -179.8(7) . . . . ?
C3 C4 C5 C6 -1.9(11) . . . . ?
C3 C4 C7 N009 176.9(7) . . . . ?
C4 C5 C6 C1 1.5(11) . . . . ?
C5 C4 C7 N009 -3.2(10) . . . . ?
C6 C1 C2 C3 -2.1(11) . . . . ?
C7 N009 C8 C9 6.6(11) . . . . ?
C7 N009 C8 C13 -174.1(7) . . . . ?
C7 C4 C5 C6 178.2(7) . . . . ?
C8 N009 C7 C4 -74.8(9) . . . . ?
C8 C9 C10 C11 0.1(11) . . . . ?
C8 C13 C14 C15 177.4(8) . . . . ?
C9 C8 C13 C12 -0.2(10) . . . . ?
C9 C8 C13 C14 -178.3(8) . . . . ?
C9 C10 C11 C12 0.7(10) . . . . ?
C9 C10 C11 C16 177.4(6) . . . . ?
C10 C11 C12 N006 176.6(6) . . . . ?
C10 C11 C12 C13 -1.3(10) . . . . ?
C10 C11 C16 O003 159.5(6) . . . . ?
C10 C11 C16 C17 -84.4(8) . . . . ?
C10 C11 C16 C20 38.6(8) . . . . ?
C11 C12 C13 C8 1.1(10) . . . . ?
C11 C12 C13 C14 179.6(6) . . . . ?
C11 C16 C17 O004 -86.4(6) . . . . ?
C11 C16 C17 O007 91.5(7) . . . . ?
C11 C16 C20 C21 178.5(6) . . . . ?
C12 N006 C15 C14 0.8(9) . . . . ?
C12 C11 C16 O003 -24.0(8) . . . . ?
C12 C11 C16 C17 92.1(7) . . . . ?
C12 C11 C16 C20 -144.9(6) . . . . ?
C12 C13 C14 C15 -0.9(8) . . . . ?
C13 C8 C9 C10 -0.4(10) . . . . ?
C13 C14 C15 N006 0.1(8) . . . . ?
C15 N006 C12 C11 -179.4(7) . . . . ?
C15 N006 C12 C13 -1.3(8) . . . . ?
C16 C11 C12 N006 0.0(11) . . . . ?
C16 C11 C12 C13 -177.9(6) . . . . ?
C16 C20 C21 C22 -172.5(6) . . . . ?
C16 C20 C21 C25 7.9(12) . . . . ?
C17 O004 C18 C19B -163(3) . . . . ?
C17 O004 C18 C19A 173(3) . . . . ?
C17 C16 C20 C21 -63.5(8) . . . . ?
C18 O004 C17 O007 -0.1(11) . . . . ?
C18 O004 C17 C16 177.8(6) . . . . ?
C20 C16 C17 O004 152.2(5) . . . . ?
C20 C16 C17 O007 -29.9(9) . . . . ?
C20 C21 C22 O002 7.2(10) . . . . ?
C20 C21 C22 N005 -175.9(6) . . . . ?
C20 C21 C25 C24 176.5(7) . . . . ?
C20 C21 C25 C26 -4.0(13) . . . . ?
C21 C25 C26 C27 178.4(7) . . . . ?
C22 N005 C24 C25 1.1(7) . . . . ?
C22 N005 C24 C29 -179.3(7) . . . . ?
C22 C21 C25 C24 -3.1(7) . . . . ?
C22 C21 C25 C26 176.3(7) . . . . ?
C23 N005 C22 O002 -0.4(11) . . . . ?
C23 N005 C22 C21 -177.5(6) . . . . ?
C23 N005 C24 C25 175.4(6) . . . . ?
C23 N005 C24 C29 -5.0(12) . . . . ?
C24 N005 C22 O002 174.0(6) . . . . ?
C24 N005 C22 C21 -3.0(7) . . . . ?
C24 C25 C26 C27 -2.2(10) . . . . ?
C25 C21 C22 O002 -173.1(6) . . . . ?
C25 C21 C22 N005 3.8(7) . . . . ?
C25 C24 C29 C28 -1.3(11) . . . . ?
C25 C26 C27 C28 1.4(11) . . . . ?
C26 C27 C28 C29 -0.5(12) . . . . ?
C27 C28 C29 C24 0.4(12) . . . . ?
C29 C24 C25 C21 -178.2(6) . . . . ?
C29 C24 C25 C26 2.2(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.614(2)
2 0.386(2)

