# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_190709xq24_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 1956699'
loop_
_audit_author_name
_audit_author_address
'Sheng-Jiao Yan'
;Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Educatio
China
;
_audit_update_record             
;
2019-09-30 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;
_audit_creation_date             2019-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H16 Br2 F N5 O5'
_chemical_formula_sum            'C29 H16 Br2 F N5 O5'
_chemical_formula_weight         693.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.834(5)
_cell_length_b                   16.568(3)
_cell_length_c                   23.084(4)
_cell_angle_alpha                90
_cell_angle_beta                 136.959(2)
_cell_angle_gamma                90
_cell_volume                     7266(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4480
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.509
_cell_measurement_theta_min      2.300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.274
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.1395 before and 0.0432 after correction. The Ratio of minimum to maximum transmission is 0.4606. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2752
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            28770
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.653
_diffrn_reflns_theta_min         2.521
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3837
_reflns_number_total             8060
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         8060
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.011
_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)+(0.0653P)²+0.5177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1441
_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 O(H) groups
2. Restrained distances
 H5-N2
 2.2 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C21, C20, C18, C17, C19, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
4.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C2(H2), C23(H23), C29(H29), C11(H11), C9(H9), C8(H8), C26(H26),
 C17(H17), C27(H27), C21(H21), C20(H20), C18(H18)
4.c Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_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 0.57905(2) 0.89538(2) 0.66626(4) 0.0874(2) Uani 1 1 d . . . . .
Br2 Br 0.90547(2) 0.21672(5) 0.66832(3) 0.1140(3) Uani 1 1 d . . . . .
F1 F 0.87966(17) -0.1606(2) 0.7424(2) 0.1329(12) Uani 1 1 d . . . . .
O2 O 0.56891(12) 0.53901(13) 0.61294(16) 0.0516(7) Uani 1 1 d . . . . .
O1 O 0.75112(13) 0.65724(14) 0.72945(18) 0.0699(8) Uani 1 1 d . . . . .
O5 O 0.64426(13) 0.39862(15) 0.50442(17) 0.0624(7) Uani 1 1 d . . . . .
H5 H 0.649690 0.422122 0.540148 0.094 Uiso 1 1 calc DGR . . . .
O3 O 0.52117(16) 0.06499(15) 0.5631(2) 0.0796(9) Uani 1 1 d . . . . .
O4 O 0.49426(18) 0.18215(17) 0.5716(3) 0.0993(12) Uani 1 1 d . . . . .
N1 N 0.60991(14) 0.42160(16) 0.61560(18) 0.0424(7) Uani 1 1 d . . . . .
N3 N 0.65897(15) 0.17197(16) 0.56740(19) 0.0452(7) Uani 1 1 d . . . . .
N2 N 0.72866(14) 0.40442(15) 0.68841(18) 0.0476(8) Uani 1 1 d D . . . .
N4 N 0.60559(17) 0.05292(16) 0.5458(2) 0.0592(9) Uani 1 1 d . . . . .
H4 H 0.585485 0.024204 0.554336 0.071 Uiso 1 1 calc R . . . .
N5 N 0.53010(18) 0.1387(2) 0.5720(2) 0.0624(9) Uani 1 1 d . . . . .
C10 C 0.66273(18) 0.37848(19) 0.6393(2) 0.0401(9) Uani 1 1 d . . . . .
C6 C 0.62370(17) 0.4987(2) 0.6375(2) 0.0429(9) Uani 1 1 d . . . . .
C4 C 0.69757(19) 0.6225(2) 0.6967(2) 0.0480(9) Uani 1 1 d . . . . .
C2 C 0.63680(19) 0.7471(2) 0.6793(2) 0.0486(10) Uani 1 1 d . . . . .
H2 H 0.676257 0.777731 0.704821 0.058 Uiso 1 1 calc R . . . .
C23 C 0.59822(18) 0.25475(19) 0.6044(2) 0.0452(9) Uani 1 1 d . . . . .
H23 H 0.576421 0.282828 0.615085 0.054 Uiso 1 1 calc R . . . .
C12 C 0.64588(17) 0.29413(19) 0.6115(2) 0.0417(9) Uani 1 1 d . . . . .
C13 C 0.67327(17) 0.2497(2) 0.5882(2) 0.0421(9) Uani 1 1 d . . . . .
C3 C 0.63628(18) 0.66394(19) 0.6678(2) 0.0443(9) Uani 1 1 d . . . . .
C24 C 0.71981(19) 0.2853(2) 0.5846(2) 0.0467(9) Uani 1 1 d . . . . .
C1 C 0.5801(2) 0.7827(2) 0.6534(2) 0.0515(10) Uani 1 1 d . . . . .
C5 C 0.68760(17) 0.53510(19) 0.6811(2) 0.0433(9) Uani 1 1 d . . . . .
C29 C 0.77980(18) 0.2437(2) 0.6209(2) 0.0534(10) Uani 1 1 d . . . . .
H29 H 0.790545 0.194620 0.647778 0.064 Uiso 1 1 calc R . . . .
C11 C 0.73937(18) 0.4824(2) 0.7071(2) 0.0467(9) Uani 1 1 d . . . . .
H11 H 0.784044 0.503144 0.739320 0.056 Uiso 1 1 calc R . . . .
C7 C 0.57586(18) 0.62097(19) 0.6296(2) 0.0438(9) Uani 1 1 d . . . . .
C14 C 0.61614(19) 0.1317(2) 0.5659(2) 0.0465(9) Uani 1 1 d . . . . .
C16 C 0.6949(2) -0.0321(2) 0.5747(3) 0.0561(10) Uani 1 1 d . U . . .
C22 C 0.58205(19) 0.17407(19) 0.5815(2) 0.0446(9) Uani 1 1 d . . . . .
C9 C 0.5210(2) 0.7388(2) 0.6172(2) 0.0563(10) Uani 1 1 d . . . . .
H9 H 0.483240 0.764328 0.601824 0.068 Uiso 1 1 calc R . . . .
C25 C 0.70398(19) 0.3590(2) 0.5431(2) 0.0517(10) Uani 1 1 d . . . . .
C8 C 0.51863(19) 0.6573(2) 0.6041(2) 0.0540(10) Uani 1 1 d . . . . .
H8 H 0.478843 0.627302 0.578452 0.065 Uiso 1 1 calc R . . . .
C15 C 0.6265(2) 0.0134(2) 0.5102(3) 0.0595(11) Uani 1 1 d . . . . .
H15A H 0.630608 0.053917 0.483723 0.071 Uiso 1 1 calc R . . . .
H15B H 0.589606 -0.023884 0.466219 0.071 Uiso 1 1 calc R . . . .
C28 C 0.8240(2) 0.2749(3) 0.6176(3) 0.0650(12) Uani 1 1 d . . . . .
C26 C 0.7495(2) 0.3884(3) 0.5408(3) 0.0704(12) Uani 1 1 d . . . . .
H26 H 0.739336 0.437148 0.513633 0.085 Uiso 1 1 calc R . . . .
C17 C 0.6973(3) -0.1100(2) 0.5991(3) 0.0760(13) Uani 1 1 d . U . . .
H17 H 0.656105 -0.133706 0.576441 0.091 Uiso 1 1 calc R . . . .
C27 C 0.8084(2) 0.3473(3) 0.5774(3) 0.0786(14) Uani 1 1 d . . . . .
H27 H 0.838229 0.367943 0.575485 0.094 Uiso 1 1 calc R . . . .
C21 C 0.7561(2) 0.0018(3) 0.6091(3) 0.0697(12) Uani 1 1 d . U . . .
H21 H 0.755703 0.054107 0.594084 0.084 Uiso 1 1 calc R . . . .
C19 C 0.8182(3) -0.1182(3) 0.6872(3) 0.0876(15) Uani 1 1 d . U . . .
C20 C 0.8187(3) -0.0409(3) 0.6661(3) 0.0926(15) Uani 1 1 d . U . . .
H20 H 0.860342 -0.017748 0.689689 0.111 Uiso 1 1 calc R . . . .
C18 C 0.7596(3) -0.1530(3) 0.6564(3) 0.0862(15) Uani 1 1 d . U . . .
H18 H 0.760866 -0.204711 0.673287 0.103 Uiso 1 1 calc R . . . .


_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 1.893(3) . ?
Br2 C28 1.888(4) . ?
F1 C19 1.363(5) . ?
O2 C6 1.353(4) . ?
O2 C7 1.386(4) . ?
O1 C4 1.216(4) . ?
O5 H5 0.8200 . ?
O5 C25 1.350(4) . ?
O3 N5 1.233(4) . ?
O4 N5 1.224(4) . ?
N1 C10 1.340(4) . ?
N1 C6 1.322(4) . ?
N3 C13 1.330(4) . ?
N3 C14 1.344(4) . ?
N2 C10 1.340(4) . ?
N2 C11 1.326(4) . ?
N4 H4 0.8600 . ?
N4 C14 1.343(4) . ?
N4 C15 1.463(4) . ?
N5 C22 1.421(4) . ?
C10 C12 1.464(4) . ?
C6 C5 1.387(4) . ?
C4 C3 1.470(5) . ?
C4 C5 1.468(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.402(4) . ?
C2 C1 1.348(5) . ?
C23 H23 0.9300 . ?
C23 C12 1.376(4) . ?
C23 C22 1.386(4) . ?
C12 C13 1.419(5) . ?
C13 C24 1.479(5) . ?
C3 C7 1.395(4) . ?
C24 C29 1.385(5) . ?
C24 C25 1.410(5) . ?
C1 C9 1.387(5) . ?
C5 C11 1.391(4) . ?
C29 H29 0.9300 . ?
C29 C28 1.387(5) . ?
C11 H11 0.9300 . ?
C7 C8 1.370(5) . ?
C14 C22 1.423(5) . ?
C16 C15 1.507(5) . ?
C16 C17 1.391(5) . ?
C16 C21 1.368(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.375(5) . ?
C25 C26 1.395(5) . ?
C8 H8 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C28 C27 1.377(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.356(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(6) . ?
C27 H27 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.384(6) . ?
C19 C20 1.374(7) . ?
C19 C18 1.344(7) . ?
C20 H20 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 C7 118.8(3) . . ?
C25 O5 H5 109.5 . . ?
C6 N1 C10 115.7(3) . . ?
C13 N3 C14 121.1(3) . . ?
C11 N2 C10 115.6(3) . . ?
C14 N4 H4 118.2 . . ?
C14 N4 C15 123.5(3) . . ?
C15 N4 H4 118.2 . . ?
O3 N5 C22 119.4(3) . . ?
O4 N5 O3 121.2(3) . . ?
O4 N5 C22 119.4(3) . . ?
N1 C10 N2 126.1(3) . . ?
N1 C10 C12 115.2(3) . . ?
N2 C10 C12 118.6(3) . . ?
O2 C6 C5 122.9(3) . . ?
N1 C6 O2 113.2(3) . . ?
N1 C6 C5 123.9(3) . . ?
O1 C4 C3 123.3(3) . . ?
O1 C4 C5 123.1(3) . . ?
C5 C4 C3 113.6(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0(3) . . ?
C12 C23 H23 119.4 . . ?
C12 C23 C22 121.3(3) . . ?
C22 C23 H23 119.4 . . ?
C23 C12 C10 118.5(3) . . ?
C23 C12 C13 116.6(3) . . ?
C13 C12 C10 124.9(3) . . ?
N3 C13 C12 122.5(3) . . ?
N3 C13 C24 114.2(3) . . ?
C12 C13 C24 123.4(3) . . ?
C2 C3 C4 121.7(3) . . ?
C7 C3 C4 120.7(3) . . ?
C7 C3 C2 117.5(3) . . ?
C29 C24 C13 119.1(3) . . ?
C29 C24 C25 118.7(3) . . ?
C25 C24 C13 122.1(3) . . ?
C2 C1 Br1 120.6(3) . . ?
C2 C1 C9 121.7(3) . . ?
C9 C1 Br1 117.7(3) . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 C11 114.5(3) . . ?
C11 C5 C4 124.2(3) . . ?
C24 C29 H29 119.8 . . ?
C24 C29 C28 120.5(4) . . ?
C28 C29 H29 119.8 . . ?
N2 C11 C5 123.7(3) . . ?
N2 C11 H11 118.1 . . ?
C5 C11 H11 118.1 . . ?
O2 C7 C3 122.3(3) . . ?
C8 C7 O2 115.4(3) . . ?
C8 C7 C3 122.3(3) . . ?
N3 C14 C22 119.4(3) . . ?
N4 C14 N3 117.2(3) . . ?
N4 C14 C22 123.3(3) . . ?
C17 C16 C15 121.1(4) . . ?
C21 C16 C15 120.5(4) . . ?
C21 C16 C17 118.5(4) . . ?
N5 C22 C14 123.3(3) . . ?
C23 C22 N5 117.8(3) . . ?
C23 C22 C14 118.8(3) . . ?
C1 C9 H9 120.2 . . ?
C8 C9 C1 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
O5 C25 C24 119.5(3) . . ?
O5 C25 C26 121.3(4) . . ?
C26 C25 C24 119.2(4) . . ?
C7 C8 C9 118.9(3) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
N4 C15 C16 113.8(3) . . ?
N4 C15 H15A 108.8 . . ?
N4 C15 H15B 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C29 C28 Br2 119.2(4) . . ?
C27 C28 Br2 120.5(3) . . ?
C27 C28 C29 120.4(4) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 C25 121.2(4) . . ?
C27 C26 H26 119.4 . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.4(5) . . ?
C18 C17 H17 119.3 . . ?
C28 C27 H27 120.0 . . ?
C26 C27 C28 120.1(4) . . ?
C26 C27 H27 120.0 . . ?
C16 C21 H21 119.7 . . ?
C16 C21 C20 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
F1 C19 C20 118.7(5) . . ?
C18 C19 F1 118.8(5) . . ?
C18 C19 C20 122.4(5) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 C21 118.8(5) . . ?
C19 C20 H20 120.6 . . ?
C17 C18 H18 120.9 . . ?
C19 C18 C17 118.3(5) . . ?
C19 C18 H18 120.9 . . ?

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 C9 C8 177.9(3) . . . . ?
Br2 C28 C27 C26 179.7(3) . . . . ?
F1 C19 C20 C21 179.1(4) . . . . ?
F1 C19 C18 C17 -178.7(4) . . . . ?
O2 C6 C5 C4 -5.7(6) . . . . ?
O2 C6 C5 C11 174.9(3) . . . . ?
O2 C7 C8 C9 -178.9(3) . . . . ?
O1 C4 C3 C2 -2.6(6) . . . . ?
O1 C4 C3 C7 179.1(4) . . . . ?
O1 C4 C5 C6 -174.7(4) . . . . ?
O1 C4 C5 C11 4.7(6) . . . . ?
O5 C25 C26 C27 -178.0(4) . . . . ?
O3 N5 C22 C23 -170.3(3) . . . . ?
O3 N5 C22 C14 12.0(6) . . . . ?
O4 N5 C22 C23 10.8(6) . . . . ?
O4 N5 C22 C14 -166.9(4) . . . . ?
N1 C10 C12 C23 -32.2(5) . . . . ?
N1 C10 C12 C13 145.5(3) . . . . ?
N1 C6 C5 C4 174.3(3) . . . . ?
N1 C6 C5 C11 -5.2(5) . . . . ?
N3 C13 C24 C29 -46.2(5) . . . . ?
N3 C13 C24 C25 131.7(4) . . . . ?
N3 C14 C22 N5 172.8(3) . . . . ?
N3 C14 C22 C23 -4.9(5) . . . . ?
N2 C10 C12 C23 144.6(3) . . . . ?
N2 C10 C12 C13 -37.7(5) . . . . ?
N4 C14 C22 N5 -4.3(6) . . . . ?
N4 C14 C22 C23 178.0(3) . . . . ?
C10 N1 C6 O2 -179.2(3) . . . . ?
C10 N1 C6 C5 0.8(5) . . . . ?
C10 N2 C11 C5 2.3(5) . . . . ?
C10 C12 C13 N3 176.6(3) . . . . ?
C10 C12 C13 C24 -3.5(5) . . . . ?
C6 O2 C7 C3 2.6(5) . . . . ?
C6 O2 C7 C8 -179.0(3) . . . . ?
C6 N1 C10 N2 6.0(5) . . . . ?
C6 N1 C10 C12 -177.4(3) . . . . ?
C6 C5 C11 N2 3.5(5) . . . . ?
C4 C3 C7 O2 -3.6(6) . . . . ?
C4 C3 C7 C8 178.1(3) . . . . ?
C4 C5 C11 N2 -176.0(3) . . . . ?
C2 C3 C7 O2 178.1(3) . . . . ?
C2 C3 C7 C8 -0.3(6) . . . . ?
C2 C1 C9 C8 -2.5(6) . . . . ?
C23 C12 C13 N3 -5.7(5) . . . . ?
C23 C12 C13 C24 174.2(3) . . . . ?
C12 C23 C22 N5 -177.4(3) . . . . ?
C12 C23 C22 C14 0.4(5) . . . . ?
C12 C13 C24 C29 133.8(4) . . . . ?
C12 C13 C24 C25 -48.3(5) . . . . ?
C13 N3 C14 N4 -178.8(3) . . . . ?
C13 N3 C14 C22 4.0(5) . . . . ?
C13 C24 C29 C28 179.0(3) . . . . ?
C13 C24 C25 O5 -0.6(5) . . . . ?
C13 C24 C25 C26 -178.8(3) . . . . ?
C3 C4 C5 C6 4.3(5) . . . . ?
C3 C4 C5 C11 -176.3(3) . . . . ?
C3 C2 C1 Br1 -178.6(3) . . . . ?
C3 C2 C1 C9 1.7(6) . . . . ?
C3 C7 C8 C9 -0.5(6) . . . . ?
C24 C29 C28 Br2 179.7(3) . . . . ?
C24 C29 C28 C27 -0.5(6) . . . . ?
C24 C25 C26 C27 0.3(6) . . . . ?
C1 C2 C3 C4 -178.7(4) . . . . ?
C1 C2 C3 C7 -0.3(5) . . . . ?
C1 C9 C8 C7 1.8(6) . . . . ?
C5 C4 C3 C2 178.4(3) . . . . ?
C5 C4 C3 C7 0.1(5) . . . . ?
C29 C24 C25 O5 177.3(3) . . . . ?
C29 C24 C25 C26 -0.9(5) . . . . ?
C29 C28 C27 C26 -0.2(7) . . . . ?
C11 N2 C10 N1 -7.5(5) . . . . ?
C11 N2 C10 C12 176.1(3) . . . . ?
C7 O2 C6 N1 -177.9(3) . . . . ?
C7 O2 C6 C5 2.1(5) . . . . ?
C14 N3 C13 C12 1.4(5) . . . . ?
C14 N3 C13 C24 -178.6(3) . . . . ?
C14 N4 C15 C16 99.2(4) . . . . ?
C16 C17 C18 C19 -1.2(7) . . . . ?
C16 C21 C20 C19 0.3(7) . . . . ?
C22 C23 C12 C10 -177.5(3) . . . . ?
C22 C23 C12 C13 4.6(5) . . . . ?
C25 C24 C29 C28 1.0(5) . . . . ?
C25 C26 C27 C28 0.3(7) . . . . ?
C15 N4 C14 N3 -12.3(5) . . . . ?
C15 N4 C14 C22 164.9(4) . . . . ?
C15 C16 C17 C18 178.1(4) . . . . ?
C15 C16 C21 C20 -177.6(4) . . . . ?
C17 C16 C15 N4 82.7(4) . . . . ?
C17 C16 C21 C20 0.8(6) . . . . ?
C21 C16 C15 N4 -98.9(4) . . . . ?
C21 C16 C17 C18 -0.3(7) . . . . ?
C20 C19 C18 C17 2.4(8) . . . . ?
C18 C19 C20 C21 -2.0(8) . . . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.047 0.250 0.203 1221 346 ' '
2 -0.058 -0.250 0.692 1221 346 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
