# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_221205a_a
_database_code_depnum_ccdc_archive 'CCDC 2290089'
loop_
_audit_author_name
_audit_author_address
'Xiangdong Fang'
;Tongji University
China
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2022-12-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1,8-Diiodo-9,10-BN-Naphthalene
_chemical_formula_moiety         '3(C8 H6 B I2 N)'
_chemical_formula_sum            'C24 H18 B3 I6 N3'
_chemical_formula_weight         1142.24
_chemical_melting_point          163.2oC
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_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                   8.561(4)
_cell_length_b                   13.824(6)
_cell_length_c                   14.980(5)
_cell_angle_alpha                109.617(9)
_cell_angle_beta                 106.009(9)
_cell_angle_gamma                102.214(7)
_cell_volume                     1512.0(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8550
_cell_measurement_temperature    283(2)
_cell_measurement_theta_max      25.791
_cell_measurement_theta_min      2.628
_shelx_estimated_absorpt_T_max   0.747
_shelx_estimated_absorpt_T_min   0.402
_exptl_absorpt_coefficient_mu    6.183
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.4908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1326 before and 0.0632 after correction.
The Ratio of minimum to maximum transmission is 0.6585.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       sheet
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25929
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.029
_diffrn_reflns_theta_min         2.712
_diffrn_ambient_temperature      283.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3878
_reflns_number_total             5961
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.139
_refine_diff_density_min         -1.801
_refine_diff_density_rms         0.183
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5961
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+7.8748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1142
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N2-C13 \\sim N2-C12
 with sigma of 0.01
 C12-C11 \\sim C14-C13
 with sigma of 0.01
 C15-C14 \\sim C11-C10
 with sigma of 0.01
 C9-C10 \\sim C16-C15
 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23)
;
_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
I1 I 1.14362(8) 0.82026(5) 0.85716(5) 0.0643(2) Uani 1 1 d . . . . .
I2 I 0.84396(8) 0.54206(5) 0.66566(5) 0.06288(19) Uani 1 1 d . . . . .
I3 I 0.94431(10) 0.68028(6) 0.48207(7) 0.0925(3) Uani 1 1 d . . . . .
I4 I 0.59128(11) 0.79143(7) 0.50173(7) 0.0903(3) Uani 1 1 d . . . . .
I5 I 0.40442(9) 0.15968(6) 0.96524(6) 0.0769(2) Uani 1 1 d . . . . .
I6 I 0.09768(9) 0.30935(6) 1.00322(6) 0.0708(2) Uani 1 1 d . . . . .
N1 N 0.5815(8) 0.7929(5) 0.7492(5) 0.0463(16) Uani 1 1 d . . . . .
N2 N 0.9059(10) 0.9234(6) 0.3438(5) 0.065(2) Uani 1 1 d D . . . .
N3 N 0.4308(9) 0.4193(5) 0.8434(5) 0.0498(17) Uani 1 1 d . . . . .
C1 C 0.9017(10) 0.8441(7) 0.8211(6) 0.0449(19) Uani 1 1 d . . . . .
C2 C 0.9124(12) 0.9492(7) 0.8692(7) 0.054(2) Uani 1 1 d . . . . .
H2 H 1.019426 1.003559 0.908655 0.065 Uiso 1 1 calc R U . . .
C3 C 0.7590(14) 0.9750(7) 0.8587(7) 0.060(2) Uani 1 1 d . . . . .
H3 H 0.767511 1.047071 0.892639 0.072 Uiso 1 1 calc R U . . .
C4 C 0.6085(13) 0.9032(8) 0.8041(7) 0.057(2) Uani 1 1 d . . . . .
H4 H 0.512798 0.925558 0.800970 0.068 Uiso 1 1 calc R U . . .
C5 C 0.6743(11) 0.6317(7) 0.6858(6) 0.047(2) Uani 1 1 d . . . . .
C6 C 0.5054(12) 0.5706(7) 0.6306(7) 0.058(2) Uani 1 1 d . . . . .
H6 H 0.474579 0.496686 0.589755 0.069 Uiso 1 1 calc R U . . .
C7 C 0.3749(12) 0.6196(8) 0.6352(7) 0.061(2) Uani 1 1 d . . . . .
H7 H 0.259927 0.576112 0.597278 0.073 Uiso 1 1 calc R U . . .
C8 C 0.4108(11) 0.7221(8) 0.6901(7) 0.052(2) Uani 1 1 d . . . . .
H8 H 0.320955 0.749899 0.690442 0.063 Uiso 1 1 calc R U . . .
C9 C 0.9630(12) 0.7792(7) 0.4027(7) 0.059(2) Uani 1 1 d D . . . .
C10 C 1.0820(15) 0.7768(10) 0.3583(9) 0.087(3) Uani 1 1 d D . . . .
H10 H 1.141144 0.727832 0.360173 0.105 Uiso 1 1 calc R U . . .
C11 C 1.1166(18) 0.8395(11) 0.3136(10) 0.105(4) Uani 1 1 d D . . . .
H11 H 1.201758 0.834463 0.286587 0.125 Uiso 1 1 calc R U . . .
C12 C 1.0352(15) 0.9130(10) 0.3038(8) 0.089(4) Uani 1 1 d D . . . .
H12 H 1.065351 0.955898 0.270734 0.107 Uiso 1 1 calc R U . . .
C13 C 0.8248(16) 1.0007(8) 0.3365(8) 0.089(4) Uani 1 1 d D . . . .
H13 H 0.862883 1.047523 0.308680 0.107 Uiso 1 1 calc R U . . .
C14 C 0.6901(17) 1.0091(8) 0.3695(7) 0.079(4) Uani 1 1 d D . . . .
H14 H 0.632465 1.056354 0.357971 0.095 Uiso 1 1 calc R U . . .
C15 C 0.6452(14) 0.9525(9) 0.4153(9) 0.085(3) Uani 1 1 d D . . . .
H15 H 0.559253 0.964275 0.439988 0.102 Uiso 1 1 calc R U . . .
C16 C 0.7126(12) 0.8754(7) 0.4315(7) 0.059(2) Uani 1 1 d D . . . .
C17 C 0.4583(11) 0.2701(7) 0.9007(7) 0.053(2) Uani 1 1 d . . . . .
C18 C 0.5842(13) 0.2630(8) 0.8633(8) 0.072(3) Uani 1 1 d . . . . .
H18 H 0.636328 0.210935 0.866254 0.087 Uiso 1 1 calc R U . . .
C19 C 0.6372(15) 0.3332(10) 0.8201(9) 0.087(4) Uani 1 1 d . . . . .
H19 H 0.728649 0.328911 0.798708 0.105 Uiso 1 1 calc R U . . .
C20 C 0.5627(15) 0.4056(8) 0.8083(7) 0.073(3) Uani 1 1 d . . . . .
H20 H 0.599277 0.447690 0.776050 0.088 Uiso 1 1 calc R U . . .
C21 C 0.3665(14) 0.4985(7) 0.8313(7) 0.062(3) Uani 1 1 d . . . . .
H21 H 0.411723 0.538855 0.799948 0.075 Uiso 1 1 calc R U . . .
C22 C 0.2420(14) 0.5201(8) 0.8625(8) 0.071(3) Uani 1 1 d . . . . .
H22 H 0.202451 0.575000 0.853022 0.085 Uiso 1 1 calc R U . . .
C23 C 0.1685(12) 0.4603(8) 0.9101(8) 0.067(3) Uani 1 1 d . . . . .
H23 H 0.079903 0.475773 0.930316 0.080 Uiso 1 1 calc R U . . .
C24 C 0.2245(11) 0.3815(7) 0.9265(6) 0.050(2) Uani 1 1 d . . . . .
B1 B 0.7280(12) 0.7527(7) 0.7515(7) 0.044(2) Uani 1 1 d . . . . .
B2 B 0.8556(13) 0.8538(8) 0.3957(7) 0.052(3) Uani 1 1 d . . . . .
B3 B 0.3658(12) 0.3518(7) 0.8925(7) 0.042(2) Uani 1 1 d . . . . .


_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
I1 C1 2.117(8) . ?
I2 C5 2.119(8) . ?
I3 C9 2.100(9) . ?
I4 C16 2.108(9) . ?
I5 C17 2.102(9) . ?
I6 C24 2.119(8) . ?
N1 C4 1.400(11) . ?
N1 C8 1.405(11) . ?
N1 B1 1.472(11) . ?
N2 C12 1.408(10) . ?
N2 C13 1.410(10) . ?
N2 B2 1.492(12) . ?
N3 C20 1.392(12) . ?
N3 C21 1.368(11) . ?
N3 B3 1.479(11) . ?
C1 C2 1.357(11) . ?
C1 B1 1.536(12) . ?
C2 H2 0.9300 . ?
C2 C3 1.414(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.283(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.358(12) . ?
C5 B1 1.516(12) . ?
C6 H6 0.9300 . ?
C6 C7 1.429(13) . ?
C7 H7 0.9300 . ?
C7 C8 1.294(12) . ?
C8 H8 0.9300 . ?
C9 C10 1.362(11) . ?
C9 B2 1.531(14) . ?
C10 H10 0.9300 . ?
C10 C11 1.296(12) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(13) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.385(13) . ?
C14 H14 0.9300 . ?
C14 C15 1.269(12) . ?
C15 H15 0.9300 . ?
C15 C16 1.373(11) . ?
C16 B2 1.512(14) . ?
C17 C18 1.352(12) . ?
C17 B3 1.528(13) . ?
C18 H18 0.9300 . ?
C18 C19 1.401(15) . ?
C19 H19 0.9300 . ?
C19 C20 1.329(15) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.326(14) . ?
C22 H22 0.9300 . ?
C22 C23 1.418(13) . ?
C23 H23 0.9300 . ?
C23 C24 1.347(12) . ?
C24 B3 1.517(12) . ?

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
C4 N1 C8 118.1(7) . . ?
C4 N1 B1 120.8(7) . . ?
C8 N1 B1 121.0(7) . . ?
C12 N2 C13 120.2(10) . . ?
C12 N2 B2 120.3(8) . . ?
C13 N2 B2 119.5(8) . . ?
C20 N3 B3 121.2(8) . . ?
C21 N3 C20 116.8(8) . . ?
C21 N3 B3 122.0(8) . . ?
C2 C1 I1 113.3(6) . . ?
C2 C1 B1 122.0(8) . . ?
B1 C1 I1 124.6(6) . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.2(8) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 118.6 . . ?
C4 C3 C2 122.7(9) . . ?
C4 C3 H3 118.6 . . ?
N1 C4 H4 118.4 . . ?
C3 C4 N1 123.2(8) . . ?
C3 C4 H4 118.4 . . ?
C6 C5 I2 113.4(6) . . ?
C6 C5 B1 120.9(8) . . ?
B1 C5 I2 125.7(6) . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.1(8) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 118.8 . . ?
C8 C7 C6 122.4(8) . . ?
C8 C7 H7 118.8 . . ?
N1 C8 H8 119.0 . . ?
C7 C8 N1 122.0(8) . . ?
C7 C8 H8 119.0 . . ?
C10 C9 I3 116.3(8) . . ?
C10 C9 B2 119.9(9) . . ?
B2 C9 I3 123.7(6) . . ?
C9 C10 H10 118.5 . . ?
C11 C10 C9 123.0(12) . . ?
C11 C10 H10 118.5 . . ?
C10 C11 H11 118.0 . . ?
C10 C11 C12 123.9(12) . . ?
C12 C11 H11 118.0 . . ?
N2 C12 H12 120.1 . . ?
C11 C12 N2 119.8(10) . . ?
C11 C12 H12 120.1 . . ?
N2 C13 H13 119.0 . . ?
C14 C13 N2 122.0(9) . . ?
C14 C13 H13 119.0 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(9) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 117.2 . . ?
C14 C15 C16 125.6(10) . . ?
C16 C15 H15 117.2 . . ?
C15 C16 I4 114.0(7) . . ?
C15 C16 B2 120.1(9) . . ?
B2 C16 I4 125.8(6) . . ?
C18 C17 I5 114.2(7) . . ?
C18 C17 B3 120.5(8) . . ?
B3 C17 I5 125.3(6) . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.7(10) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 118.5 . . ?
C20 C19 C18 123.1(10) . . ?
C20 C19 H19 118.5 . . ?
N3 C20 H20 119.5 . . ?
C19 C20 N3 121.0(9) . . ?
C19 C20 H20 119.5 . . ?
N3 C21 H21 118.8 . . ?
C22 C21 N3 122.5(8) . . ?
C22 C21 H21 118.8 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.7(9) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.3(9) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 I6 113.2(7) . . ?
C23 C24 B3 121.1(8) . . ?
B3 C24 I6 125.7(6) . . ?
N1 B1 C1 111.9(7) . . ?
N1 B1 C5 113.5(7) . . ?
C5 B1 C1 134.6(8) . . ?
N2 B2 C9 112.9(8) . . ?
N2 B2 C16 112.4(8) . . ?
C16 B2 C9 134.7(9) . . ?
N3 B3 C17 113.5(7) . . ?
N3 B3 C24 112.5(7) . . ?
C24 B3 C17 134.0(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 C3 -174.8(6) . . . . ?
I1 C1 B1 N1 174.3(5) . . . . ?
I1 C1 B1 C5 -5.4(13) . . . . ?
I2 C5 C6 C7 -179.4(6) . . . . ?
I2 C5 B1 N1 178.9(5) . . . . ?
I2 C5 B1 C1 -1.4(13) . . . . ?
I3 C9 C10 C11 -174.7(11) . . . . ?
I3 C9 B2 N2 174.3(6) . . . . ?
I3 C9 B2 C16 -3.9(15) . . . . ?
I4 C16 B2 N2 176.7(6) . . . . ?
I4 C16 B2 C9 -5.0(15) . . . . ?
I5 C17 C18 C19 -178.5(8) . . . . ?
I5 C17 B3 N3 -180.0(5) . . . . ?
I5 C17 B3 C24 2.1(14) . . . . ?
I6 C24 B3 N3 -178.5(5) . . . . ?
I6 C24 B3 C17 -0.6(14) . . . . ?
N2 C13 C14 C15 5.8(17) . . . . ?
N3 C21 C22 C23 -0.3(15) . . . . ?
C1 C2 C3 C4 -0.9(14) . . . . ?
C2 C1 B1 N1 -2.9(11) . . . . ?
C2 C1 B1 C5 177.4(9) . . . . ?
C2 C3 C4 N1 -0.6(14) . . . . ?
C4 N1 C8 C7 178.3(8) . . . . ?
C4 N1 B1 C1 1.5(10) . . . . ?
C4 N1 B1 C5 -178.7(7) . . . . ?
C5 C6 C7 C8 0.6(14) . . . . ?
C6 C5 B1 N1 0.9(11) . . . . ?
C6 C5 B1 C1 -179.4(8) . . . . ?
C6 C7 C8 N1 0.1(14) . . . . ?
C8 N1 C4 C3 -178.5(8) . . . . ?
C8 N1 B1 C1 -180.0(7) . . . . ?
C8 N1 B1 C5 -0.2(10) . . . . ?
C9 C10 C11 C12 -2(2) . . . . ?
C10 C9 B2 N2 -3.8(13) . . . . ?
C10 C9 B2 C16 177.9(10) . . . . ?
C10 C11 C12 N2 0(2) . . . . ?
C12 N2 C13 C14 176.1(10) . . . . ?
C12 N2 B2 C9 2.5(11) . . . . ?
C12 N2 B2 C16 -178.9(8) . . . . ?
C13 N2 C12 C11 178.3(11) . . . . ?
C13 N2 B2 C9 -176.6(8) . . . . ?
C13 N2 B2 C16 2.1(11) . . . . ?
C13 C14 C15 C16 -4.1(19) . . . . ?
C14 C15 C16 I4 -176.0(10) . . . . ?
C14 C15 C16 B2 1.4(17) . . . . ?
C15 C16 B2 N2 -0.4(13) . . . . ?
C15 C16 B2 C9 177.9(10) . . . . ?
C17 C18 C19 C20 -3.7(18) . . . . ?
C18 C17 B3 N3 -1.1(12) . . . . ?
C18 C17 B3 C24 -179.1(9) . . . . ?
C18 C19 C20 N3 3.2(18) . . . . ?
C20 N3 C21 C22 -179.3(9) . . . . ?
C20 N3 B3 C17 0.6(11) . . . . ?
C20 N3 B3 C24 179.0(8) . . . . ?
C21 N3 C20 C19 177.6(10) . . . . ?
C21 N3 B3 C17 -178.6(7) . . . . ?
C21 N3 B3 C24 -0.2(11) . . . . ?
C21 C22 C23 C24 1.1(16) . . . . ?
C22 C23 C24 I6 178.1(7) . . . . ?
C22 C23 C24 B3 -1.4(14) . . . . ?
C23 C24 B3 N3 1.0(12) . . . . ?
C23 C24 B3 C17 178.9(9) . . . . ?
B1 N1 C4 C3 0.1(12) . . . . ?
B1 N1 C8 C7 -0.3(12) . . . . ?
B1 C1 C2 C3 2.7(12) . . . . ?
B1 C5 C6 C7 -1.1(12) . . . . ?
B2 N2 C12 C11 -0.8(15) . . . . ?
B2 N2 C13 C14 -4.8(14) . . . . ?
B2 C9 C10 C11 3.6(18) . . . . ?
B3 N3 C20 C19 -1.7(14) . . . . ?
B3 N3 C21 C22 -0.1(13) . . . . ?
B3 C17 C18 C19 2.6(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_210409a_a
_database_code_depnum_ccdc_archive 'CCDC 2290262'
loop_
_audit_author_name
_audit_author_address
'Xiangdong Fang'
;Tongji University
China
;
_audit_update_record             
;
2023-08-23 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2021-04-12
_diffrn_source_power             1.2
_audit_creation_method           
;
FinalCif V85 by Daniel Kratzert, Freiburg 2021,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C8 H5 B Cl2 N2 O2'
_chemical_formula_moiety         '1(C8 H5 B Cl2 N2 O2)'
_chemical_formula_weight         242.85
_exptl_crystal_colour_primary    colourless
_chemical_melting_point          ?
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2757(5)
_cell_length_b                   10.6008(4)
_cell_length_c                   13.6875(6)
_cell_angle_alpha                98.866(2)
_cell_angle_beta                 97.836(2)
_cell_angle_gamma                99.621(2)
_cell_volume                     1432.20(11)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7879
_cell_measurement_theta_min      2.744
_cell_measurement_theta_max      25.021
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_vrf_PLAT088_210409a_a           
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.90 Note  
RESPONSE: More parameters were used because of the diorder. 
;
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6679
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0561 before and 0.0474 after correction.
The Ratio of minimum to maximum transmission is 0.8963.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      100.0
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_collimation    0.3
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_source_current           24.0
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            15752
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_theta_min         2.712
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5033
_reflns_number_gt                4055
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+2.8243P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5033
_refine_ls_number_parameters     814
_refine_ls_number_restraints     1533
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_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.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C10-C11 \\sim C10-C9
 with sigma of 0.01
 C14-N4 \\sim C11A-N4A
 with sigma of 0.01
 N6A-O5A \\sim N6-O6A
 with sigma of 0.01
 C22-N6 \\sim C19A-N6A
 with sigma of 0.02
 C6-N2 \\sim C3A-N2A
 with sigma of 0.01
 N4A-O4A \\sim N4A-O3A
 with sigma of 0.01
 N2A-O1A \\sim N2A-O2A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.04 within 2A
Uanis(Cl1A) \\sim Ueq, Uanis(O5A) \\sim Ueq, Uanis(O4A) \\sim Ueq: with sigma
of 0.006 and sigma for terminal atoms of 0.012
Uanis(Cl4A) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(O6) \\sim Ueq, Uanis(O6A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Same fragment restrains
{C9, C10, C11, C12, B2, N3, C13, C14, C15, C16, Cl3, Cl4} sigma for 1-2: 0.02,
1-3: 0.04
as in
{C9A, C10A, C11A, C12A, B2A, N3A, C13A, C14A, C15A, C16A, Cl3A, Cl4A}
{C17, C18, C19, C20, B3, N5, C21, C22, C23, C24, Cl5, Cl6} sigma for 1-2: 0.02,
1-3: 0.04
as in
{C17A, C18A, C19A, C20A, B3A, N5A, C21A, C22A, C23A, C24A, Cl5A, Cl6A}
{C1, C2, C3, C4, B1, N1, C5, C6, C7, C8, Cl1, Cl2} sigma for 1-2: 0.02, 1-3:
0.04
as in
{C1A, C2A, C3A, C4A, B1A, N1A, C5A, C6A, C7A, C8A, Cl1A, Cl2A}
5. Others
 Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C4A)=Sof(H4A)=Sof(B1A)=Sof(N1A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(Cl1A)=
 Sof(Cl2A)=Sof(N2A)=Sof(O1A)=Sof(O2A)=1-FVAR(1)
 Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(B1)=Sof(N1)=
 Sof(C5)=Sof(H5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(Cl1)=Sof(Cl2)=Sof(N2)=
 Sof(O1)=Sof(O2)=FVAR(1)
 Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(C20A)=Sof(H20A)=Sof(B3A)=Sof(N5A)=
 Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=
 Sof(Cl5A)=Sof(Cl6A)=Sof(N6A)=Sof(O5A)=Sof(O6A)=1-FVAR(2)
 Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(B3)=
 Sof(N5)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(Cl5)=
 Sof(Cl6)=Sof(N6)=Sof(O5)=Sof(O6)=FVAR(2)
 Sof(C9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(B2A)=Sof(N3A)=
 Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(Cl3A)=Sof(Cl4A)=Sof(N4A)=Sof(O4A)=Sof(O3A)=1-FVAR(3)
 Sof(C9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(B2)=Sof(N3)=
 Sof(C13)=Sof(H13)=Sof(C14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(Cl3)=Sof(Cl4)=
 Sof(N4)=Sof(O3)=Sof(O4)=FVAR(3)
6.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C10A(H10A), C12A(H12A),
 C13A(H13A), C14A(H14A), C15A(H15A), C18(H18), C19(H19), C20(H20), C21(H21),
 C23(H23), C18A(H18A), C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A), C2(H2),
 C3(H3), C4(H4), C5(H5), C7(H7), C2A(H2A), C4A(H4A), C5A(H5A), C6A(H6A),
 C7A(H7A)
;

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
C9 C 0.3805(4) 0.7939(4) 0.3889(3) 0.0242(9) Uani 0.829(3) 1 d D U P A 1
C10 C 0.3230(6) 0.8957(5) 0.4247(5) 0.0289(14) Uani 0.829(3) 1 d D U P A 1
H10 H 0.354626 0.943506 0.490674 0.035 Uiso 0.829(3) 1 calc R U P A 1
C11 C 0.2173(4) 0.9294(4) 0.3637(3) 0.0301(10) Uani 0.829(3) 1 d D U P A 1
H11 H 0.179345 1.000304 0.390380 0.036 Uiso 0.829(3) 1 calc R U P A 1
C12 C 0.1676(6) 0.8670(7) 0.2702(4) 0.0256(13) Uani 0.829(3) 1 d D U P A 1
H12 H 0.096584 0.894431 0.232111 0.031 Uiso 0.829(3) 1 calc R U P A 1
B2 B 0.3284(9) 0.7153(9) 0.2834(5) 0.0223(13) Uani 0.829(3) 1 d D U P A 1
N3 N 0.2200(3) 0.7609(3) 0.2279(2) 0.0217(7) Uani 0.829(3) 1 d D U P A 1
C13 C 0.1637(7) 0.7028(7) 0.1315(5) 0.0215(12) Uani 0.829(3) 1 d D U P A 1
H13 H 0.093613 0.735254 0.096835 0.026 Uiso 0.829(3) 1 calc R U P A 1
C14 C 0.2077(4) 0.5991(4) 0.0855(3) 0.0208(9) Uani 0.829(3) 1 d D U P A 1
C15 C 0.3102(5) 0.5431(6) 0.1318(4) 0.0219(11) Uani 0.829(3) 1 d D U P A 1
H15 H 0.336649 0.469563 0.096874 0.026 Uiso 0.829(3) 1 calc R U P A 1
C16 C 0.3696(4) 0.5971(4) 0.2272(3) 0.0219(9) Uani 0.829(3) 1 d D U P A 1
Cl3 Cl 0.49304(13) 0.52147(12) 0.28024(9) 0.0330(3) Uani 0.829(3) 1 d D U P A 1
Cl4 Cl 0.5145(3) 0.7614(3) 0.4679(2) 0.0332(6) Uani 0.829(3) 1 d D U P A 1
N4 N 0.1458(3) 0.5433(3) -0.0176(3) 0.0262(8) Uani 0.829(3) 1 d D U P A 1
O3 O 0.1720(7) 0.4397(7) -0.0568(4) 0.0392(14) Uani 0.829(3) 1 d . U P A 1
O4 O 0.0660(5) 0.5992(5) -0.0620(3) 0.0328(10) Uani 0.829(3) 1 d . U P A 1
C9A C 0.2534(17) 0.8505(17) 0.3394(11) 0.022(3) Uani 0.171(3) 1 d D U P A 2
C10A C 0.145(3) 0.889(3) 0.2903(17) 0.024(5) Uani 0.171(3) 1 d D U P A 2
H10A H 0.105931 0.956319 0.321891 0.029 Uiso 0.171(3) 1 calc R U P A 2
C11A C 0.0948(17) 0.8247(17) 0.1906(12) 0.024(4) Uani 0.171(3) 1 d D U P A 2
C12A C 0.139(4) 0.726(4) 0.141(2) 0.024(5) Uani 0.171(3) 1 d D U P A 2
H12A H 0.102077 0.690908 0.072919 0.029 Uiso 0.171(3) 1 calc R U P A 2
B2A B 0.309(5) 0.734(5) 0.291(2) 0.024(5) Uani 0.171(3) 1 d D U P A 2
N3A N 0.2408(15) 0.6732(15) 0.1911(11) 0.024(3) Uani 0.171(3) 1 d D U P A 2
C13A C 0.274(3) 0.566(3) 0.137(2) 0.026(5) Uani 0.171(3) 1 d D U P A 2
H13A H 0.224796 0.526788 0.072589 0.031 Uiso 0.171(3) 1 calc R U P A 2
C14A C 0.381(2) 0.517(2) 0.1775(14) 0.032(4) Uani 0.171(3) 1 d D U P A 2
H14A H 0.407352 0.446435 0.138923 0.038 Uiso 0.171(3) 1 calc R U P A 2
C15A C 0.453(2) 0.570(2) 0.2745(13) 0.022(4) Uani 0.171(3) 1 d D U P A 2
H15A H 0.523276 0.530319 0.300302 0.026 Uiso 0.171(3) 1 calc R U P A 2
C16A C 0.4252(18) 0.6732(17) 0.3320(12) 0.030(4) Uani 0.171(3) 1 d D U P A 2
Cl3A Cl 0.5292(19) 0.7316(19) 0.4466(12) 0.054(4) Uani 0.171(3) 1 d D U P A 2
Cl4A Cl 0.3224(8) 0.9355(7) 0.4606(5) 0.0291(18) Uani 0.171(3) 1 d D U P A 2
N4A N -0.0125(15) 0.8724(16) 0.1354(10) 0.031(4) Uani 0.171(3) 1 d D U P A 2
O4A O -0.040(2) 0.827(2) 0.0422(14) 0.034(5) Uani 0.171(3) 1 d D U P A 2
O3A O -0.071(3) 0.954(2) 0.180(2) 0.032(6) Uani 0.171(3) 1 d D U P A 2
C17 C 0.0111(4) 0.7619(4) 0.5005(3) 0.0247(9) Uani 0.828(3) 1 d D U P B 1
C18 C -0.0932(7) 0.7908(6) 0.4438(5) 0.0318(16) Uani 0.828(3) 1 d D U P B 1
H18 H -0.132924 0.861150 0.468983 0.038 Uiso 0.828(3) 1 calc R U P B 1
C19 C -0.1450(5) 0.7166(5) 0.3459(4) 0.0339(11) Uani 0.828(3) 1 d D U P B 1
H19 H -0.219492 0.738586 0.307679 0.041 Uiso 0.828(3) 1 calc R U P B 1
C20 C -0.0922(8) 0.6166(6) 0.3056(5) 0.0296(15) Uani 0.828(3) 1 d D U P B 1
H20 H -0.129212 0.570249 0.239903 0.036 Uiso 0.828(3) 1 calc R U P B 1
B3 B 0.0758(13) 0.6476(12) 0.4627(6) 0.0209(13) Uani 0.828(3) 1 d D U P B 1
N5 N 0.0165(3) 0.5809(3) 0.3600(2) 0.0222(8) Uani 0.828(3) 1 d D U P B 1
C21 C 0.0620(8) 0.4767(6) 0.3142(4) 0.0214(14) Uani 0.828(3) 1 d D U P B 1
H21 H 0.021769 0.435579 0.247746 0.026 Uiso 0.828(3) 1 calc R U P B 1
C22 C 0.1639(4) 0.4315(4) 0.3626(3) 0.0220(9) Uani 0.828(3) 1 d D U P B 1
C23 C 0.2295(6) 0.4868(6) 0.4619(4) 0.0208(12) Uani 0.828(3) 1 d D U P B 1
H23 H 0.300325 0.451973 0.493207 0.025 Uiso 0.828(3) 1 calc R U P B 1
C24 C 0.1890(4) 0.5900(4) 0.5108(3) 0.0214(9) Uani 0.828(3) 1 d D U P B 1
Cl5 Cl 0.27329(13) 0.65359(12) 0.63280(9) 0.0295(3) Uani 0.828(3) 1 d D U P B 1
Cl6 Cl 0.0669(3) 0.8594(2) 0.61911(17) 0.0366(5) Uani 0.828(3) 1 d D U P B 1
N6 N 0.2048(4) 0.3184(3) 0.3086(3) 0.0287(9) Uani 0.828(3) 1 d D U P B 1
O5 O 0.2812(6) 0.2642(6) 0.3575(4) 0.0415(13) Uani 0.828(3) 1 d . U P B 1
O6 O 0.1625(5) 0.2825(5) 0.2194(3) 0.0410(12) Uani 0.828(3) 1 d . U P B 1
C17A C -0.0534(18) 0.7058(17) 0.3899(12) 0.026(3) Uani 0.172(3) 1 d D U P B 2
C18A C -0.102(4) 0.651(3) 0.2942(17) 0.025(5) Uani 0.172(3) 1 d D U P B 2
H18A H -0.172387 0.681004 0.257620 0.030 Uiso 0.172(3) 1 calc R U P B 2
C19A C -0.0471(18) 0.5474(17) 0.2482(11) 0.025(3) Uani 0.172(3) 1 d D U P B 2
C20A C 0.052(4) 0.498(3) 0.2942(18) 0.024(5) Uani 0.172(3) 1 d D U P B 2
H20A H 0.085349 0.428546 0.259467 0.028 Uiso 0.172(3) 1 calc R U P B 2
B3A B 0.058(7) 0.658(6) 0.452(3) 0.020(5) Uani 0.172(3) 1 d D U P B 2
N5A N 0.1043(15) 0.5510(14) 0.3943(10) 0.024(3) Uani 0.172(3) 1 d D U P B 2
C21A C 0.204(3) 0.493(3) 0.4346(18) 0.025(5) Uani 0.172(3) 1 d D U P B 2
H21A H 0.229312 0.421047 0.396188 0.030 Uiso 0.172(3) 1 calc R U P B 2
C22A C 0.265(2) 0.540(2) 0.5317(15) 0.033(4) Uani 0.172(3) 1 d D U P B 2
H22A H 0.335909 0.502568 0.558599 0.039 Uiso 0.172(3) 1 calc R U P B 2
C23A C 0.228(2) 0.642(2) 0.5940(17) 0.034(5) Uani 0.172(3) 1 d D U P B 2
H23A H 0.271671 0.668496 0.661705 0.041 Uiso 0.172(3) 1 calc R U P B 2
C24A C 0.1319(17) 0.7035(16) 0.5587(11) 0.023(3) Uani 0.172(3) 1 d D U P B 2
Cl5A Cl 0.0890(16) 0.8266(13) 0.6411(9) 0.053(3) Uani 0.172(3) 1 d D U P B 2
Cl6A Cl -0.1254(9) 0.8318(8) 0.4425(6) 0.035(2) Uani 0.172(3) 1 d D U P B 2
N6A N -0.0879(17) 0.4982(16) 0.1414(11) 0.028(4) Uani 0.172(3) 1 d D U P B 2
O5A O -0.052(3) 0.395(3) 0.1040(15) 0.034(6) Uani 0.172(3) 1 d . U P B 2
O6A O -0.172(5) 0.547(4) 0.090(2) 0.063(11) Uani 0.172(3) 1 d . U P B 2
C1 C 0.5492(4) -0.1456(4) 0.1357(3) 0.0263(9) Uani 0.829(2) 1 d D U P C 1
C2 C 0.5989(6) -0.0738(6) 0.2289(5) 0.0268(13) Uani 0.829(2) 1 d D U P C 1
H2 H 0.673807 -0.093715 0.268230 0.032 Uiso 0.829(2) 1 calc R U P C 1
C3 C 0.5389(4) 0.0308(4) 0.2674(3) 0.0287(10) Uani 0.829(2) 1 d D U P C 1
H3 H 0.573618 0.077736 0.333244 0.034 Uiso 0.829(2) 1 calc R U P C 1
C4 C 0.4361(7) 0.0657(7) 0.2148(4) 0.0259(13) Uani 0.829(2) 1 d D U P C 1
H4 H 0.400515 0.137088 0.243626 0.031 Uiso 0.829(2) 1 calc R U P C 1
B1 B 0.4312(8) -0.1126(8) 0.0709(5) 0.0204(12) Uani 0.829(2) 1 d D U P C 1
N1 N 0.3795(3) -0.0013(3) 0.1178(2) 0.0214(7) Uani 0.829(2) 1 d D U P C 1
C5 C 0.2750(9) 0.0425(8) 0.0689(5) 0.0219(12) Uani 0.829(2) 1 d D U P C 1
H5 H 0.243778 0.114566 0.101552 0.026 Uiso 0.829(2) 1 calc R U P C 1
C6 C 0.2159(4) -0.0160(4) -0.0253(3) 0.0226(9) Uani 0.829(2) 1 d D U P C 1
C7 C 0.2545(6) -0.1250(6) -0.0799(4) 0.0221(11) Uani 0.829(2) 1 d D U P C 1
H7 H 0.209525 -0.163392 -0.145773 0.026 Uiso 0.829(2) 1 calc R U P C 1
C8 C 0.3572(4) -0.1728(4) -0.0354(3) 0.0227(9) Uani 0.829(2) 1 d D U P C 1
Cl1 Cl 0.6296(4) -0.2711(4) 0.0949(2) 0.0325(6) Uani 0.829(2) 1 d D U P C 1
Cl2 Cl 0.39877(12) -0.30826(11) -0.10558(9) 0.0287(3) Uani 0.829(2) 1 d D U P C
1
N2 N 0.1102(4) 0.0397(4) -0.0741(3) 0.0298(9) Uani 0.829(2) 1 d D U P C 1
O1 O 0.0660(4) 0.1260(4) -0.0250(3) 0.0332(10) Uani 0.829(2) 1 d . U P C 1
O2 O 0.0687(7) -0.0027(6) -0.1628(5) 0.0487(17) Uani 0.829(2) 1 d . U P C 1
C1A C 0.4986(17) -0.0257(17) 0.2017(12) 0.024(3) Uani 0.171(2) 1 d D U P C 2
C2A C 0.439(4) 0.067(4) 0.2461(19) 0.030(5) Uani 0.171(2) 1 d D U P C 2
H2A H 0.468285 0.105900 0.314657 0.036 Uiso 0.171(2) 1 calc R U P C 2
C3A C 0.3315(19) 0.1059(17) 0.1887(13) 0.028(4) Uani 0.171(2) 1 d D U P C 2
C4A C 0.278(5) 0.056(4) 0.094(2) 0.022(5) Uani 0.171(2) 1 d D U P C 2
H4A H 0.208364 0.089693 0.059943 0.027 Uiso 0.171(2) 1 calc R U P C 2
B1A B 0.441(4) -0.094(4) 0.093(2) 0.026(5) Uani 0.171(2) 1 d D U P C 2
N1A N 0.3262(15) -0.0483(15) 0.0443(11) 0.027(3) Uani 0.171(2) 1 d D U P C 2
C5A C 0.259(3) -0.099(3) -0.0514(17) 0.026(5) Uani 0.171(2) 1 d D U P C 2
H5A H 0.186306 -0.063639 -0.079179 0.031 Uiso 0.171(2) 1 calc R U P C 2
C6A C 0.2983(19) -0.201(2) -0.1055(14) 0.031(4) Uani 0.171(2) 1 d D U P C 2
H6A H 0.250693 -0.238084 -0.170820 0.038 Uiso 0.171(2) 1 calc R U P C 2
C7A C 0.410(2) -0.252(2) -0.0658(14) 0.032(5) Uani 0.171(2) 1 d D U P C 2
H7A H 0.434945 -0.320858 -0.107107 0.038 Uiso 0.171(2) 1 calc R U P C 2
C8A C 0.4814(18) -0.2075(17) 0.0273(13) 0.029(4) Uani 0.171(2) 1 d D U P C 2
Cl1A Cl 0.6373(8) -0.0632(8) 0.2694(6) 0.0336(19) Uani 0.171(2) 1 d D U P C 2
Cl2A Cl 0.610(2) -0.288(2) 0.0643(12) 0.043(4) Uani 0.171(2) 1 d D U P C 2
N2A N 0.2721(17) 0.2088(16) 0.2374(11) 0.030(4) Uani 0.171(2) 1 d D U P C 2
O1A O 0.196(2) 0.260(2) 0.1838(17) 0.041(5) Uani 0.171(2) 1 d D U P C 2
O2A O 0.308(4) 0.243(4) 0.3303(19) 0.057(8) Uani 0.171(2) 1 d D U P C 2


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
C9 C10 1.373(6) . ?
C9 B2 1.528(7) . ?
C9 Cl4 1.747(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.406(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.336(7) . ?
C12 H12 0.9500 . ?
C12 N3 1.407(6) . ?
B2 N3 1.454(6) . ?
B2 C16 1.520(7) . ?
N3 C13 1.370(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.356(7) . ?
C14 C15 1.415(6) . ?
C14 N4 1.456(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.357(7) . ?
C16 Cl3 1.746(4) . ?
N4 O3 1.235(8) . ?
N4 O4 1.237(6) . ?
C9A C10A 1.377(18) . ?
C9A B2A 1.540(17) . ?
C9A Cl4A 1.752(14) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.414(18) . ?
C11A C12A 1.339(19) . ?
C11A N4A 1.455(11) . ?
C12A H12A 0.9500 . ?
C12A N3A 1.409(19) . ?
B2A N3A 1.450(16) . ?
B2A C16A 1.530(17) . ?
N3A C13A 1.378(17) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.374(18) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.409(17) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.341(17) . ?
C16A Cl3A 1.734(16) . ?
N4A O4A 1.268(19) . ?
N4A O3A 1.265(19) . ?
C17 C18 1.343(8) . ?
C17 B3 1.532(7) . ?
C17 Cl6 1.750(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.428(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.347(7) . ?
C20 H20 0.9500 . ?
C20 N5 1.396(7) . ?
B3 N5 1.471(6) . ?
B3 C24 1.520(7) . ?
N5 C21 1.367(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.357(7) . ?
C22 C23 1.422(6) . ?
C22 N6 1.463(5) . ?
C23 H23 0.9500 . ?
C23 C24 1.349(7) . ?
C24 Cl5 1.749(4) . ?
N6 O5 1.234(7) . ?
N6 O6 1.216(5) . ?
C17A C18A 1.339(19) . ?
C17A B3A 1.535(17) . ?
C17A Cl6A 1.741(14) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.418(19) . ?
C19A C20A 1.349(19) . ?
C19A N6A 1.453(16) . ?
C20A H20A 0.9500 . ?
C20A N5A 1.394(19) . ?
B3A N5A 1.462(16) . ?
B3A C24A 1.517(17) . ?
N5A C21A 1.376(18) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.370(19) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.406(18) . ?
C23A H23A 0.9500 . ?
C23A C24A 1.345(18) . ?
C24A Cl5A 1.744(15) . ?
N6A O5A 1.27(3) . ?
N6A O6A 1.26(4) . ?
C1 C2 1.365(8) . ?
C1 B1 1.525(7) . ?
C1 Cl1 1.740(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.423(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.332(7) . ?
C4 H4 0.9500 . ?
C4 N1 1.403(7) . ?
B1 N1 1.468(6) . ?
B1 C8 1.533(7) . ?
N1 C5 1.372(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.352(7) . ?
C6 C7 1.421(6) . ?
C6 N2 1.455(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.357(7) . ?
C8 Cl2 1.748(4) . ?
N2 O1 1.236(5) . ?
N2 O2 1.218(7) . ?
C1A C2A 1.355(19) . ?
C1A B1A 1.545(17) . ?
C1A Cl1A 1.729(14) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.420(19) . ?
C3A C4A 1.331(19) . ?
C3A N2A 1.454(11) . ?
C4A H4A 0.9500 . ?
C4A N1A 1.400(19) . ?
B1A N1A 1.464(16) . ?
B1A C8A 1.534(17) . ?
N1A C5A 1.376(18) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.362(19) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.422(18) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.353(18) . ?
C8A Cl2A 1.747(17) . ?
N2A O1A 1.25(2) . ?
N2A O2A 1.25(2) . ?

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
C10 C9 B2 120.2(4) . . ?
C10 C9 Cl4 117.2(4) . . ?
B2 C9 Cl4 122.6(3) . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.1(5) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 118.3 . . ?
C12 C11 C10 123.4(5) . . ?
C12 C11 H11 118.3 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 N3 120.2(5) . . ?
N3 C12 H12 119.9 . . ?
N3 B2 C9 114.3(5) . . ?
N3 B2 C16 114.7(4) . . ?
C16 B2 C9 131.0(4) . . ?
C12 N3 B2 121.8(4) . . ?
C13 N3 C12 116.4(4) . . ?
C13 N3 B2 121.8(4) . . ?
N3 C13 H13 119.9 . . ?
C14 C13 N3 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 123.8(4) . . ?
C13 C14 N4 117.6(4) . . ?
C15 C14 N4 118.6(4) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.4(4) . . ?
C16 C15 H15 120.8 . . ?
B2 C16 Cl3 122.9(3) . . ?
C15 C16 B2 121.1(4) . . ?
C15 C16 Cl3 116.0(3) . . ?
O3 N4 C14 118.7(4) . . ?
O3 N4 O4 122.2(4) . . ?
O4 N4 C14 119.1(4) . . ?
C10A C9A B2A 121.4(14) . . ?
C10A C9A Cl4A 117.4(13) . . ?
B2A C9A Cl4A 121.2(11) . . ?
C9A C10A H10A 121.5 . . ?
C9A C10A C11A 116.9(16) . . ?
C11A C10A H10A 121.5 . . ?
C10A C11A N4A 117.2(14) . . ?
C12A C11A C10A 126.0(16) . . ?
C12A C11A N4A 116.8(15) . . ?
C11A C12A H12A 120.2 . . ?
C11A C12A N3A 119.5(18) . . ?
N3A C12A H12A 120.2 . . ?
N3A B2A C9A 114.7(13) . . ?
N3A B2A C16A 114.9(13) . . ?
C16A B2A C9A 130.3(13) . . ?
C12A N3A B2A 121.0(15) . . ?
C13A N3A C12A 115.8(15) . . ?
C13A N3A B2A 123.1(15) . . ?
N3A C13A H13A 120.6 . . ?
C14A C13A N3A 118.8(19) . . ?
C14A C13A H13A 120.6 . . ?
C13A C14A H14A 119.0 . . ?
C13A C14A C15A 121.9(18) . . ?
C15A C14A H14A 119.0 . . ?
C14A C15A H15A 118.7 . . ?
C16A C15A C14A 122.6(18) . . ?
C16A C15A H15A 118.7 . . ?
B2A C16A Cl3A 124.6(12) . . ?
C15A C16A B2A 118.5(14) . . ?
C15A C16A Cl3A 116.8(13) . . ?
O4A N4A C11A 115.2(14) . . ?
O3A N4A C11A 120.3(18) . . ?
O3A N4A O4A 124.5(19) . . ?
C18 C17 B3 121.0(5) . . ?
C18 C17 Cl6 116.7(4) . . ?
B3 C17 Cl6 122.3(3) . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.5(5) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 118.7 . . ?
C20 C19 C18 122.6(5) . . ?
C20 C19 H19 118.7 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 N5 120.2(5) . . ?
N5 C20 H20 119.9 . . ?
N5 B3 C17 113.6(4) . . ?
N5 B3 C24 114.0(4) . . ?
C24 B3 C17 132.4(4) . . ?
C20 N5 B3 122.1(4) . . ?
C21 N5 C20 116.4(4) . . ?
C21 N5 B3 121.5(4) . . ?
N5 C21 H21 119.6 . . ?
C22 C21 N5 120.7(4) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 123.4(4) . . ?
C21 C22 N6 117.1(4) . . ?
C23 C22 N6 119.5(4) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 C22 118.4(5) . . ?
C24 C23 H23 120.8 . . ?
B3 C24 Cl5 121.7(3) . . ?
C23 C24 B3 121.9(4) . . ?
C23 C24 Cl5 116.3(4) . . ?
O5 N6 C22 117.0(4) . . ?
O6 N6 C22 119.4(4) . . ?
O6 N6 O5 123.6(4) . . ?
C18A C17A B3A 121.8(15) . . ?
C18A C17A Cl6A 117.0(14) . . ?
B3A C17A Cl6A 121.1(12) . . ?
C17A C18A H18A 120.4 . . ?
C17A C18A C19A 119.1(18) . . ?
C19A C18A H18A 120.4 . . ?
C18A C19A N6A 119.3(15) . . ?
C20A C19A C18A 124.6(16) . . ?
C20A C19A N6A 115.7(16) . . ?
C19A C20A H20A 121.0 . . ?
C19A C20A N5A 118.1(19) . . ?
N5A C20A H20A 121.0 . . ?
N5A B3A C17A 112.6(13) . . ?
N5A B3A C24A 115.0(13) . . ?
C24A B3A C17A 132.4(14) . . ?
C20A N5A B3A 123.7(15) . . ?
C21A N5A C20A 113.5(16) . . ?
C21A N5A B3A 122.7(15) . . ?
N5A C21A H21A 120.9 . . ?
C22A C21A N5A 118(2) . . ?
C22A C21A H21A 120.9 . . ?
C21A C22A H22A 118.1 . . ?
C21A C22A C23A 123.8(19) . . ?
C23A C22A H22A 118.1 . . ?
C22A C23A H23A 119.7 . . ?
C24A C23A C22A 120.7(18) . . ?
C24A C23A H23A 119.7 . . ?
B3A C24A Cl5A 122.2(12) . . ?
C23A C24A B3A 119.6(14) . . ?
C23A C24A Cl5A 118.1(13) . . ?
O5A N6A C19A 118.4(17) . . ?
O6A N6A C19A 120(2) . . ?
O6A N6A O5A 121(2) . . ?
C2 C1 B1 120.4(4) . . ?
C2 C1 Cl1 116.8(4) . . ?
B1 C1 Cl1 122.7(3) . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(5) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 118.6 . . ?
C4 C3 C2 122.7(5) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 N1 121.2(5) . . ?
N1 C4 H4 119.4 . . ?
C1 B1 C8 131.9(4) . . ?
N1 B1 C1 114.5(4) . . ?
N1 B1 C8 113.6(4) . . ?
C4 N1 B1 121.1(4) . . ?
C5 N1 C4 117.1(4) . . ?
C5 N1 B1 121.8(4) . . ?
N1 C5 H5 119.7 . . ?
C6 C5 N1 120.7(5) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C7 123.9(4) . . ?
C5 C6 N2 117.5(4) . . ?
C7 C6 N2 118.5(4) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 C6 118.2(4) . . ?
C8 C7 H7 120.9 . . ?
B1 C8 Cl2 122.0(3) . . ?
C7 C8 B1 121.8(4) . . ?
C7 C8 Cl2 116.1(4) . . ?
O1 N2 C6 119.5(4) . . ?
O2 N2 C6 117.4(4) . . ?
O2 N2 O1 123.1(4) . . ?
C2A C1A B1A 119.1(15) . . ?
C2A C1A Cl1A 118.6(14) . . ?
B1A C1A Cl1A 122.3(12) . . ?
C1A C2A H2A 120.5 . . ?
C1A C2A C3A 119.0(18) . . ?
C3A C2A H2A 120.5 . . ?
C2A C3A N2A 117.8(15) . . ?
C4A C3A C2A 126.1(16) . . ?
C4A C3A N2A 116.1(16) . . ?
C3A C4A H4A 120.6 . . ?
C3A C4A N1A 118.7(19) . . ?
N1A C4A H4A 120.6 . . ?
N1A B1A C1A 115.7(13) . . ?
N1A B1A C8A 114.0(13) . . ?
C8A B1A C1A 130.2(14) . . ?
C4A N1A B1A 121.1(15) . . ?
C5A N1A C4A 114.4(16) . . ?
C5A N1A B1A 124.5(15) . . ?
N1A C5A H5A 120.6 . . ?
C6A C5A N1A 119(2) . . ?
C6A C5A H5A 120.6 . . ?
C5A C6A H6A 119.5 . . ?
C5A C6A C7A 121.0(18) . . ?
C7A C6A H6A 119.5 . . ?
C6A C7A H7A 118.0 . . ?
C8A C7A C6A 124.0(18) . . ?
C8A C7A H7A 118.0 . . ?
B1A C8A Cl2A 125.4(12) . . ?
C7A C8A B1A 117.6(14) . . ?
C7A C8A Cl2A 117.0(13) . . ?
O1A N2A C3A 118.2(16) . . ?
O1A N2A O2A 125(2) . . ?
O2A N2A C3A 116.4(18) . . ?

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
C9 C10 C11 C12 -0.1(9) . . . . ?
C9 B2 N3 C12 -1.2(12) . . . . ?
C9 B2 N3 C13 178.7(7) . . . . ?
C9 B2 C16 C15 -179.0(9) . . . . ?
C9 B2 C16 Cl3 1.8(14) . . . . ?
C10 C9 B2 N3 1.6(11) . . . . ?
C10 C9 B2 C16 -177.7(9) . . . . ?
C10 C11 C12 N3 0.5(10) . . . . ?
C11 C12 N3 B2 0.2(10) . . . . ?
C11 C12 N3 C13 -179.7(6) . . . . ?
C12 N3 C13 C14 -179.5(6) . . . . ?
B2 C9 C10 C11 -1.1(9) . . . . ?
B2 N3 C13 C14 0.6(11) . . . . ?
N3 B2 C16 C15 1.7(12) . . . . ?
N3 B2 C16 Cl3 -177.6(5) . . . . ?
N3 C13 C14 C15 0.9(11) . . . . ?
N3 C13 C14 N4 -178.8(5) . . . . ?
C13 C14 C15 C16 -1.0(9) . . . . ?
C13 C14 N4 O3 -171.1(6) . . . . ?
C13 C14 N4 O4 6.9(7) . . . . ?
C14 C15 C16 B2 -0.3(9) . . . . ?
C14 C15 C16 Cl3 179.0(4) . . . . ?
C15 C14 N4 O3 9.2(7) . . . . ?
C15 C14 N4 O4 -172.8(5) . . . . ?
C16 B2 N3 C12 178.3(6) . . . . ?
C16 B2 N3 C13 -1.8(12) . . . . ?
Cl4 C9 C10 C11 178.1(4) . . . . ?
Cl4 C9 B2 N3 -177.5(5) . . . . ?
Cl4 C9 B2 C16 3.1(14) . . . . ?
N4 C14 C15 C16 178.6(4) . . . . ?
C9A C10A C11A C12A 3(5) . . . . ?
C9A C10A C11A N4A -175(3) . . . . ?
C9A B2A N3A C12A 5(7) . . . . ?
C9A B2A N3A C13A -179(3) . . . . ?
C9A B2A C16A C15A 179(5) . . . . ?
C9A B2A C16A Cl3A -3(8) . . . . ?
C10A C9A B2A N3A 1(7) . . . . ?
C10A C9A B2A C16A -179(5) . . . . ?
C10A C11A C12A N3A 3(6) . . . . ?
C10A C11A N4A O4A 169(3) . . . . ?
C10A C11A N4A O3A -11(4) . . . . ?
C11A C12A N3A B2A -7(6) . . . . ?
C11A C12A N3A C13A 176(3) . . . . ?
C12A C11A N4A O4A -9(4) . . . . ?
C12A C11A N4A O3A 171(3) . . . . ?
C12A N3A C13A C14A 174(3) . . . . ?
B2A C9A C10A C11A -5(6) . . . . ?
B2A N3A C13A C14A -3(6) . . . . ?
N3A B2A C16A C15A -1(6) . . . . ?
N3A B2A C16A Cl3A 177(3) . . . . ?
N3A C13A C14A C15A 3(5) . . . . ?
C13A C14A C15A C16A -3(4) . . . . ?
C14A C15A C16A B2A 2(5) . . . . ?
C14A C15A C16A Cl3A -176(2) . . . . ?
C16A B2A N3A C12A -175(4) . . . . ?
C16A B2A N3A C13A 2(7) . . . . ?
Cl4A C9A C10A C11A 177(2) . . . . ?
Cl4A C9A B2A N3A 179(3) . . . . ?
Cl4A C9A B2A C16A -1(8) . . . . ?
N4A C11A C12A N3A -179(3) . . . . ?
C17 C18 C19 C20 -0.7(10) . . . . ?
C17 B3 N5 C20 -2.7(16) . . . . ?
C17 B3 N5 C21 180.0(8) . . . . ?
C17 B3 C24 C23 179.9(12) . . . . ?
C17 B3 C24 Cl5 0(2) . . . . ?
C18 C17 B3 N5 2.6(16) . . . . ?
C18 C17 B3 C24 -177.4(12) . . . . ?
C18 C19 C20 N5 0.6(10) . . . . ?
C19 C20 N5 B3 1.3(12) . . . . ?
C19 C20 N5 C21 178.7(6) . . . . ?
C20 N5 C21 C22 -177.4(6) . . . . ?
B3 C17 C18 C19 -1.0(12) . . . . ?
B3 N5 C21 C22 0.0(12) . . . . ?
N5 B3 C24 C23 -0.1(16) . . . . ?
N5 B3 C24 Cl5 -179.7(7) . . . . ?
N5 C21 C22 C23 0.1(10) . . . . ?
N5 C21 C22 N6 179.1(5) . . . . ?
C21 C22 C23 C24 -0.2(9) . . . . ?
C21 C22 N6 O5 -168.4(6) . . . . ?
C21 C22 N6 O6 11.4(7) . . . . ?
C22 C23 C24 B3 0.2(11) . . . . ?
C22 C23 C24 Cl5 179.8(4) . . . . ?
C23 C22 N6 O5 10.6(7) . . . . ?
C23 C22 N6 O6 -169.6(5) . . . . ?
C24 B3 N5 C20 177.2(8) . . . . ?
C24 B3 N5 C21 0.0(16) . . . . ?
Cl6 C17 C18 C19 179.8(5) . . . . ?
Cl6 C17 B3 N5 -178.2(7) . . . . ?
Cl6 C17 B3 C24 2(2) . . . . ?
N6 C22 C23 C24 -179.1(5) . . . . ?
C17A C18A C19A C20A 0(5) . . . . ?
C17A C18A C19A N6A -173(3) . . . . ?
C17A B3A N5A C20A 0(9) . . . . ?
C17A B3A N5A C21A -180(4) . . . . ?
C17A B3A C24A C23A -180(6) . . . . ?
C17A B3A C24A Cl5A 5(11) . . . . ?
C18A C17A B3A N5A 1(8) . . . . ?
C18A C17A B3A C24A 179(6) . . . . ?
C18A C19A C20A N5A 0(6) . . . . ?
C18A C19A N6A O5A -171(3) . . . . ?
C18A C19A N6A O6A 0(4) . . . . ?
C19A C20A N5A B3A 0(7) . . . . ?
C19A C20A N5A C21A 179(3) . . . . ?
C20A C19A N6A O5A 16(4) . . . . ?
C20A C19A N6A O6A -174(4) . . . . ?
C20A N5A C21A C22A 178(3) . . . . ?
B3A C17A C18A C19A -1(6) . . . . ?
B3A N5A C21A C22A -2(6) . . . . ?
N5A B3A C24A C23A -2(8) . . . . ?
N5A B3A C24A Cl5A -178(4) . . . . ?
N5A C21A C22A C23A 3(5) . . . . ?
C21A C22A C23A C24A -3(4) . . . . ?
C22A C23A C24A B3A 3(5) . . . . ?
C22A C23A C24A Cl5A 179(2) . . . . ?
C24A B3A N5A C20A -178(4) . . . . ?
C24A B3A N5A C21A 2(9) . . . . ?
Cl6A C17A C18A C19A -180(2) . . . . ?
Cl6A C17A B3A N5A 180(4) . . . . ?
Cl6A C17A B3A C24A -3(11) . . . . ?
N6A C19A C20A N5A 174(3) . . . . ?
C1 C2 C3 C4 -1.9(9) . . . . ?
C1 B1 N1 C4 -0.7(11) . . . . ?
C1 B1 N1 C5 178.9(7) . . . . ?
C1 B1 C8 C7 -178.6(8) . . . . ?
C1 B1 C8 Cl2 2.3(13) . . . . ?
C2 C1 B1 N1 -0.2(11) . . . . ?
C2 C1 B1 C8 178.6(8) . . . . ?
C2 C3 C4 N1 0.9(10) . . . . ?
C3 C4 N1 B1 0.3(10) . . . . ?
C3 C4 N1 C5 -179.2(7) . . . . ?
C4 N1 C5 C6 179.3(8) . . . . ?
B1 C1 C2 C3 1.4(9) . . . . ?
B1 N1 C5 C6 -0.3(13) . . . . ?
N1 B1 C8 C7 0.2(11) . . . . ?
N1 B1 C8 Cl2 -178.8(5) . . . . ?
N1 C5 C6 C7 0.6(13) . . . . ?
N1 C5 C6 N2 -177.0(7) . . . . ?
C5 C6 C7 C8 -0.5(11) . . . . ?
C5 C6 N2 O1 -9.4(8) . . . . ?
C5 C6 N2 O2 171.1(7) . . . . ?
C6 C7 C8 B1 0.1(10) . . . . ?
C6 C7 C8 Cl2 179.2(4) . . . . ?
C7 C6 N2 O1 172.9(5) . . . . ?
C7 C6 N2 O2 -6.6(7) . . . . ?
C8 B1 N1 C4 -179.7(6) . . . . ?
C8 B1 N1 C5 -0.2(11) . . . . ?
Cl1 C1 C2 C3 179.7(4) . . . . ?
Cl1 C1 B1 N1 -178.4(5) . . . . ?
Cl1 C1 B1 C8 0.4(13) . . . . ?
N2 C6 C7 C8 177.1(5) . . . . ?
C1A C2A C3A C4A 3(6) . . . . ?
C1A C2A C3A N2A -178(3) . . . . ?
C1A B1A N1A C4A 3(7) . . . . ?
C1A B1A N1A C5A -178(3) . . . . ?
C1A B1A C8A C7A 178(4) . . . . ?
C1A B1A C8A Cl2A 0(8) . . . . ?
C2A C1A B1A N1A 2(6) . . . . ?
C2A C1A B1A C8A -175(5) . . . . ?
C2A C3A C4A N1A 2(7) . . . . ?
C2A C3A N2A O1A 167(3) . . . . ?
C2A C3A N2A O2A -9(4) . . . . ?
C3A C4A N1A B1A -5(7) . . . . ?
C3A C4A N1A C5A 176(4) . . . . ?
C4A C3A N2A O1A -14(4) . . . . ?
C4A C3A N2A O2A 170(4) . . . . ?
C4A N1A C5A C6A -180(4) . . . . ?
B1A C1A C2A C3A -5(6) . . . . ?
B1A N1A C5A C6A 1(6) . . . . ?
N1A B1A C8A C7A 0(6) . . . . ?
N1A B1A C8A Cl2A -178(3) . . . . ?
N1A C5A C6A C7A -2(5) . . . . ?
C5A C6A C7A C8A 2(4) . . . . ?
C6A C7A C8A B1A -1(4) . . . . ?
C6A C7A C8A Cl2A 177(2) . . . . ?
C8A B1A N1A C4A -179(4) . . . . ?
C8A B1A N1A C5A -1(6) . . . . ?
Cl1A C1A C2A C3A 175(3) . . . . ?
Cl1A C1A B1A N1A -178(3) . . . . ?
Cl1A C1A B1A C8A 5(7) . . . . ?
N2A C3A C4A N1A -177(3) . . . . ?

####################################################################### 
# 
# 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_210322b_a
_database_code_depnum_ccdc_archive 'CCDC 2290263'
loop_
_audit_author_name
_audit_author_address
'Xiangdong Fang'
;Tongji University
China
;
_audit_update_record             
;
2023-08-23 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_vrf_PLAT088_210322b_a           
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.90 Note  
RESPONSE: More parameters were used because of the diorder.
;
_audit_creation_date             2021-04-13
_diffrn_source_power             1.2
_audit_creation_method           
;
FinalCif V85 by Daniel Kratzert, Freiburg 2021,
https://github.com/dkratzert/FinalCif
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C8 H5 B Br2 N2 O2'
_chemical_formula_moiety         'C8 H5 B Br2 N2 O2'
_chemical_formula_weight         331.77
_exptl_crystal_colour_primary    yellow
_chemical_melting_point          ?
_olex2_submission_special_instructions 'No special instructions were received'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.6162(12)
_cell_length_b                   10.7945(11)
_cell_length_c                   13.7859(16)
_cell_angle_alpha                98.209(4)
_cell_angle_beta                 97.619(4)
_cell_angle_gamma                98.727(4)
_cell_volume                     1526.2(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    6992
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.26
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.166
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    7.944
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.5135
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1130 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.6891.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.382
_shelx_estimated_absorpt_T_max   0.504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      190.0
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_collimation    0.3
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_source_current           24.0
_diffrn_detector                 CPAD
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_detector_area_resol_mean 7.41
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_reflns_number            15784
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_theta_min         2.647
_diffrn_reflns_theta_max         25.351
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5532
_reflns_number_gt                4474
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0858P)²+11.2837P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5532
_refine_ls_number_parameters     802
_refine_ls_number_restraints     1467
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1685
_refine_ls_wR_factor_gt          0.1562
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      0.930
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8629(14)
2 0.1371(14)

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'
B B 0.0013 0.0007 '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'
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'

_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.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8629(14)
 0.1371(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 N4A-O4A
 1.24 with sigma of 0.01
 C10-C11 \\sim C10-C9
 with sigma of 0.01
 C14-N4 \\sim C11A-N4A
 with sigma of 0.01
 C22-N6 \\sim C19A-N6A
 with sigma of 0.02
 C6-N2 \\sim C3A-N2A
 with sigma of 0.01
 N4A-O3A \\sim N4A-O4A \\sim N4-O3 \\sim N4-O4
 with sigma of 0.006
 N6A-O5A \\sim N6A-O6A
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.02 and sigma
for terminal atoms of 0.04 within 2A
Uanis(Br1A) \\sim Ueq: with sigma of 0.006 and sigma for terminal atoms of 0.012
Uanis(Br4A) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(O6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N6A) \\sim Ueq, Uanis(O3A) \\sim Ueq, Uanis(O4A) \\sim Ueq, Uanis(O2A)
\\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(O1A) \\sim Ueq: with sigma of 0.006 and sigma for terminal atoms of 0.012
5. Same fragment restrains
{C9, C10, C11, C12, B2, N3, C13, C14, C15, C16, Br3, Br4} sigma for 1-2: 0.02,
1-3: 0.04
as in
{C9A, C10A, C11A, C12A, B2A, N3A, C13A, C14A, C15A, C16A, Br3A, Br4A}
{C17, C18, C19, C20, B3, N5, C21, C22, C23, C24, Br5, Br6} sigma for 1-2: 0.02,
1-3: 0.04
as in
{C17A, C18A, C19A, C20A, B3A, N5A, C21A, C22A, C23A, C24A, Br5A, Br6A}
{C1, C2, C3, C4, B1, N1, C5, C6, C7, C8, Br1, Br2} sigma for 1-2: 0.02, 1-3:
0.04
as in
{C1A, C2A, C3A, C4A, B1A, N1A, C5A, C6A, C7A, C8A, Br1A, Br2A}
6. Others
 Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(C4A)=Sof(H4A)=Sof(B1A)=Sof(N1A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(Br1A)=
 Sof(Br2A)=Sof(N2A)=Sof(O1A)=Sof(O2A)=1-FVAR(1)
 Sof(C1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(B1)=Sof(N1)=
 Sof(C5)=Sof(H5)=Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(Br1)=Sof(Br2)=Sof(N2)=
 Sof(O1)=Sof(O2)=FVAR(1)
 Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(C20A)=Sof(H20A)=Sof(B3A)=Sof(N5A)=
 Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=
 Sof(Br5A)=Sof(Br6A)=Sof(N6A)=Sof(O5A)=Sof(O6A)=1-FVAR(2)
 Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(B3)=
 Sof(N5)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(Br5)=
 Sof(Br6)=Sof(N6)=Sof(O5)=Sof(O6)=FVAR(2)
 Sof(C9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(B2A)=Sof(N3A)=
 Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(Br3A)=Sof(Br4A)=Sof(N4A)=Sof(O3A)=Sof(O4A)=1-FVAR(3)
 Sof(C9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(B2)=Sof(N3)=
 Sof(C13)=Sof(H13)=Sof(C14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(Br3)=Sof(Br4)=
 Sof(N4)=Sof(O3)=Sof(O4)=FVAR(3)
7.a Free rotating group:
 N6A(O5A,O6A)
7.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C10A(H10A), C12A(H12A),
 C13A(H13A), C14A(H14A), C15A(H15A), C18(H18), C19(H19), C20(H20), C21(H21),
 C23(H23), C18A(H18A), C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A), C2(H2),
 C3(H3), C4(H4), C5(H5), C7(H7), C2A(H2A), C4A(H4A), C5A(H5A), C6A(H6A),
 C7A(H7A)
;

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
C9 C 0.3704(11) 0.7946(11) 0.3827(8) 0.038(2) Uani 0.927(4) 1 d D U P A 1
C10 C 0.3119(11) 0.8954(12) 0.4177(11) 0.044(3) Uani 0.927(4) 1 d D U P A 1
H10 H 0.342722 0.943020 0.482186 0.053 Uiso 0.927(4) 1 calc R U P A 1
C11 C 0.2075(12) 0.9268(12) 0.3582(8) 0.045(3) Uani 0.927(4) 1 d D U P A 1
H11 H 0.167722 0.994552 0.384512 0.054 Uiso 0.927(4) 1 calc R U P A 1
C12 C 0.1600(13) 0.8634(14) 0.2628(9) 0.040(3) Uani 0.927(4) 1 d D U P A 1
H12 H 0.091632 0.890010 0.223722 0.048 Uiso 0.927(4) 1 calc R U P A 1
B2 B 0.3170(15) 0.7158(15) 0.2793(10) 0.033(2) Uani 0.927(4) 1 d D U P A 1
N3 N 0.2130(9) 0.7609(9) 0.2248(7) 0.0343(18) Uani 0.927(4) 1 d D U P A 1
C13 C 0.1591(12) 0.7038(14) 0.1292(8) 0.036(2) Uani 0.927(4) 1 d D U P A 1
H13 H 0.091547 0.735872 0.093858 0.043 Uiso 0.927(4) 1 calc R U P A 1
C14 C 0.2038(11) 0.6011(11) 0.0859(7) 0.035(2) Uani 0.927(4) 1 d D U P A 1
C15 C 0.3003(12) 0.5463(12) 0.1323(8) 0.038(3) Uani 0.927(4) 1 d D U P A 1
H15 H 0.324334 0.471966 0.099545 0.045 Uiso 0.927(4) 1 calc R U P A 1
C16 C 0.3580(10) 0.5988(10) 0.2223(8) 0.032(2) Uani 0.927(4) 1 d D U P A 1
Br3 Br 0.48732(13) 0.51428(13) 0.28329(9) 0.0473(4) Uani 0.927(4) 1 d D U P A 1
Br4 Br 0.51601(16) 0.7690(2) 0.46912(12) 0.0496(4) Uani 0.927(4) 1 d D U P A 1
N4 N 0.1433(9) 0.5463(8) -0.0167(7) 0.044(2) Uani 0.927(4) 1 d D U P A 1
O3 O 0.1703(12) 0.4443(11) -0.0543(8) 0.060(3) Uani 0.927(4) 1 d D U P A 1
O4 O 0.0695(9) 0.6048(9) -0.0628(7) 0.054(3) Uani 0.927(4) 1 d D U P A 1
C9A C 0.254(9) 0.844(9) 0.332(5) 0.038(5) Uani 0.073(4) 1 d D U P A 2
C10A C 0.147(14) 0.883(14) 0.284(8) 0.039(6) Uani 0.073(4) 1 d D U P A 2
H10A H 0.117942 0.956673 0.312136 0.047 Uiso 0.073(4) 1 calc R U P A 2
C11A C 0.084(8) 0.813(8) 0.192(5) 0.036(6) Uani 0.073(4) 1 d D U P A 2
C12A C 0.134(13) 0.719(13) 0.139(6) 0.035(6) Uani 0.073(4) 1 d D U P A 2
H12A H 0.101488 0.689138 0.070449 0.042 Uiso 0.073(4) 1 calc R U P A 2
B2A B 0.306(15) 0.730(13) 0.281(8) 0.035(5) Uani 0.073(4) 1 d D U P A 2
N3A N 0.231(7) 0.668(7) 0.187(4) 0.035(5) Uani 0.073(4) 1 d D U P A 2
C13A C 0.251(11) 0.553(9) 0.139(7) 0.035(6) Uani 0.073(4) 1 d D U P A 2
H13A H 0.193811 0.509086 0.081514 0.042 Uiso 0.073(4) 1 calc R U P A 2
C14A C 0.355(9) 0.503(8) 0.176(5) 0.035(7) Uani 0.073(4) 1 d D U P A 2
H14A H 0.382762 0.437948 0.134622 0.042 Uiso 0.073(4) 1 calc R U P A 2
C15A C 0.420(10) 0.543(6) 0.273(5) 0.037(8) Uani 0.073(4) 1 d D U P A 2
H15A H 0.468316 0.489815 0.305274 0.044 Uiso 0.073(4) 1 calc R U P A 2
C16A C 0.414(8) 0.658(7) 0.317(5) 0.036(6) Uani 0.073(4) 1 d D U P A 2
Br3A Br 0.520(2) 0.714(2) 0.4450(18) 0.061(7) Uani 0.073(4) 1 d D U P A 2
Br4A Br 0.3167(16) 0.9390(17) 0.4615(13) 0.042(5) Uani 0.073(4) 1 d D U P A 2
N4A N -0.015(8) 0.873(8) 0.139(5) 0.034(12) Uani 0.073(4) 1 d D U P A 2
O3A O -0.044(12) 0.855(12) 0.047(5) 0.03(2) Uani 0.073(4) 1 d D U P A 2
O4A O -0.083(10) 0.945(9) 0.175(9) 0.04(2) Uani 0.073(4) 1 d D U P A 2
C17 C 0.0115(11) 0.7583(11) 0.4951(7) 0.037(2) Uani 0.924(4) 1 d D U P B 1
C18 C -0.0904(16) 0.7870(15) 0.4382(11) 0.044(3) Uani 0.924(4) 1 d D U P B 1
H18 H -0.130991 0.854633 0.463394 0.053 Uiso 0.924(4) 1 calc R U P B 1
C19 C -0.1384(13) 0.7167(12) 0.3403(9) 0.046(3) Uani 0.924(4) 1 d D U P B 1
H19 H -0.207889 0.740679 0.300482 0.055 Uiso 0.924(4) 1 calc R U P B 1
C20 C -0.0860(15) 0.6177(12) 0.3046(8) 0.044(3) Uani 0.924(4) 1 d D U P B 1
H20 H -0.121846 0.570875 0.240660 0.053 Uiso 0.924(4) 1 calc R U P B 1
B3 B 0.0763(16) 0.6470(15) 0.4599(9) 0.033(2) Uani 0.924(4) 1 d D U P B 1
N5 N 0.0190(9) 0.5810(9) 0.3579(6) 0.0351(19) Uani 0.924(4) 1 d D U P B 1
C21 C 0.0626(13) 0.4778(11) 0.3129(8) 0.036(3) Uani 0.924(4) 1 d D U P B 1
H21 H 0.024395 0.438650 0.247286 0.044 Uiso 0.924(4) 1 calc R U P B 1
C22 C 0.1608(11) 0.4306(11) 0.3616(8) 0.036(2) Uani 0.924(4) 1 d D U P B 1
C23 C 0.2232(12) 0.4844(12) 0.4582(8) 0.033(2) Uani 0.924(4) 1 d D U P B 1
H23 H 0.291064 0.448699 0.489342 0.040 Uiso 0.924(4) 1 calc R U P B 1
C24 C 0.1855(10) 0.5881(10) 0.5067(7) 0.031(2) Uani 0.924(4) 1 d D U P B 1
Br5 Br 0.27252(12) 0.65065(12) 0.63833(8) 0.0445(4) Uani 0.924(4) 1 d D U P B 1
Br6 Br 0.0686(2) 0.86682(18) 0.62069(13) 0.0524(5) Uani 0.924(4) 1 d D U P B 1
N6 N 0.2014(10) 0.3186(10) 0.3112(8) 0.045(2) Uani 0.924(4) 1 d D U P B 1
O5 O 0.2678(11) 0.2624(10) 0.3578(8) 0.056(3) Uani 0.924(4) 1 d . U P B 1
O6 O 0.1639(12) 0.2858(10) 0.2220(8) 0.064(3) Uani 0.924(4) 1 d . U P B 1
C17A C -0.046(10) 0.697(9) 0.386(4) 0.039(5) Uani 0.076(4) 1 d D U P B 2
C18A C -0.088(15) 0.648(15) 0.289(5) 0.041(6) Uani 0.076(4) 1 d D U P B 2
H18A H -0.157051 0.678452 0.254167 0.049 Uiso 0.076(4) 1 calc R U P B 2
C19A C -0.032(10) 0.549(10) 0.239(4) 0.039(6) Uani 0.076(4) 1 d D U P B 2
C20A C 0.064(12) 0.505(12) 0.290(4) 0.037(6) Uani 0.076(4) 1 d D U P B 2
H20A H 0.107943 0.447483 0.254064 0.044 Uiso 0.076(4) 1 calc R U P B 2
B3A B 0.062(16) 0.651(15) 0.448(6) 0.035(5) Uani 0.076(4) 1 d D U P B 2
N5A N 0.103(7) 0.539(6) 0.392(3) 0.035(5) Uani 0.076(4) 1 d D U P B 2
C21A C 0.211(12) 0.493(13) 0.430(5) 0.033(6) Uani 0.076(4) 1 d D U P B 2
H21A H 0.241224 0.427337 0.391440 0.040 Uiso 0.076(4) 1 calc R U P B 2
C22A C 0.273(8) 0.545(10) 0.524(5) 0.038(7) Uani 0.076(4) 1 d D U P B 2
H22A H 0.359494 0.534041 0.542758 0.045 Uiso 0.076(4) 1 calc R U P B 2
C23A C 0.213(10) 0.615(8) 0.593(4) 0.039(8) Uani 0.076(4) 1 d D U P B 2
H23A H 0.236184 0.617455 0.662518 0.047 Uiso 0.076(4) 1 calc R U P B 2
C24A C 0.121(9) 0.680(7) 0.558(4) 0.038(6) Uani 0.076(4) 1 d D U P B 2
Br5A Br 0.106(2) 0.831(2) 0.6425(18) 0.054(6) Uani 0.076(4) 1 d D U P B 2
Br6A Br -0.129(2) 0.829(2) 0.4411(14) 0.054(5) Uani 0.076(4) 1 d D U P B 2
N6A N -0.068(9) 0.495(8) 0.134(3) 0.034(11) Uani 0.076(4) 1 d DG U P B 2
O5A O -0.028(10) 0.396(8) 0.101(7) 0.039(19) Uiso 0.076(4) 1 d DG U P B 2
O6A O -0.138(11) 0.544(10) 0.077(7) 0.03(2) Uiso 0.076(4) 1 d DG U P B 2
C1 C 0.5440(12) 0.8588(11) 0.1412(8) 0.039(2) Uani 0.915(4) 1 d D U P C 1
C2 C 0.5884(15) 0.9274(13) 0.2300(10) 0.040(3) Uani 0.915(4) 1 d D U P C 1
H2 H 0.660332 0.907288 0.269690 0.049 Uiso 0.915(4) 1 calc R U P C 1
C3 C 0.5291(13) 1.0323(12) 0.2674(9) 0.045(3) Uani 0.915(4) 1 d D U P C 1
H3 H 0.563900 1.079867 0.331319 0.054 Uiso 0.915(4) 1 calc R U P C 1
C4 C 0.4271(13) 1.0655(14) 0.2158(9) 0.037(2) Uani 0.915(4) 1 d D U P C 1
H4 H 0.389800 1.133827 0.244325 0.045 Uiso 0.915(4) 1 calc R U P C 1
B1 B 0.4273(14) 0.8923(14) 0.0740(9) 0.033(2) Uani 0.915(4) 1 d D U P C 1
N1 N 0.3748(9) 1.0002(9) 0.1202(7) 0.0358(19) Uani 0.915(4) 1 d D U P C 1
C5 C 0.2749(12) 1.0432(13) 0.0717(8) 0.033(2) Uani 0.915(4) 1 d D U P C 1
H5 H 0.244375 1.114521 0.103052 0.039 Uiso 0.915(4) 1 calc R U P C 1
C6 C 0.2181(11) 0.9860(11) -0.0209(8) 0.038(2) Uani 0.915(4) 1 d D U P C 1
C7 C 0.2580(12) 0.8820(12) -0.0741(8) 0.034(2) Uani 0.915(4) 1 d D U P C 1
H7 H 0.215923 0.846388 -0.139551 0.041 Uiso 0.915(4) 1 calc R U P C 1
C8 C 0.3586(11) 0.8324(11) -0.0304(8) 0.033(2) Uani 0.915(4) 1 d D U P C 1
Br1 Br 0.6332(2) 0.7255(2) 0.09910(15) 0.0457(4) Uani 0.915(4) 1 d D U P C 1
Br2 Br 0.40183(13) 0.69025(12) -0.10695(8) 0.0428(4) Uani 0.915(4) 1 d D U P C
1
N2 N 0.1132(10) 1.0424(10) -0.0706(8) 0.044(2) Uani 0.915(4) 1 d D U P C 1
O1 O 0.0700(11) 1.1267(11) -0.0220(9) 0.055(3) Uani 0.915(4) 1 d . U P C 1
O2 O 0.0761(12) 1.0039(13) -0.1577(8) 0.069(4) Uani 0.915(4) 1 d . U P C 1
C1A C 0.485(7) 0.975(8) 0.200(4) 0.039(5) Uani 0.085(4) 1 d D U P C 2
C2A C 0.442(10) 1.076(11) 0.240(8) 0.039(6) Uani 0.085(4) 1 d D U P C 2
H2A H 0.492031 1.133505 0.295427 0.047 Uiso 0.085(4) 1 calc R U P C 2
C3A C 0.317(7) 1.097(8) 0.198(4) 0.037(6) Uani 0.085(4) 1 d D U P C 2
C4A C 0.272(12) 1.058(12) 0.100(5) 0.036(6) Uani 0.085(4) 1 d D U P C 2
H4A H 0.209434 1.098428 0.067062 0.043 Uiso 0.085(4) 1 calc R U P C 2
B1A B 0.424(11) 0.901(11) 0.095(5) 0.035(5) Uani 0.085(4) 1 d D U P C 2
N1A N 0.319(7) 0.958(7) 0.048(4) 0.035(5) Uani 0.085(4) 1 d D U P C 2
C5A C 0.257(10) 0.910(11) -0.045(5) 0.034(6) Uani 0.085(4) 1 d D U P C 2
H5A H 0.184259 0.942836 -0.071912 0.041 Uiso 0.085(4) 1 calc R U P C 2
C6A C 0.300(7) 0.815(8) -0.101(4) 0.034(7) Uani 0.085(4) 1 d D U P C 2
H6A H 0.246054 0.769703 -0.159723 0.041 Uiso 0.085(4) 1 calc R U P C 2
C7A C 0.422(7) 0.784(9) -0.074(3) 0.035(8) Uani 0.085(4) 1 d D U P C 2
H7A H 0.470592 0.753665 -0.122229 0.042 Uiso 0.085(4) 1 calc R U P C 2
C8A C 0.468(8) 0.798(8) 0.026(3) 0.036(6) Uani 0.085(4) 1 d D U P C 2
Br1A Br 0.6380(17) 0.9359(18) 0.2681(15) 0.054(5) Uani 0.085(4) 1 d D U P C 2
Br2A Br 0.602(2) 0.706(2) 0.059(2) 0.060(6) Uani 0.085(4) 1 d D U P C 2
N2A N 0.262(10) 1.210(7) 0.236(8) 0.044(12) Uani 0.085(4) 1 d D U P C 2
O1A O 0.159(12) 1.260(12) 0.177(10) 0.06(2) Uani 0.085(4) 1 d . U P C 2
O2A O 0.313(9) 1.296(9) 0.335(7) 0.030(18) Uani 0.085(4) 1 d . U P C 2


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
C9 C10 1.392(13) . ?
C9 B2 1.540(15) . ?
C9 Br4 1.903(11) . ?
C10 H10 0.9500 . ?
C10 C11 1.404(13) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(17) . ?
C12 H12 0.9500 . ?
C12 N3 1.384(15) . ?
B2 N3 1.439(15) . ?
B2 C16 1.541(16) . ?
N3 C13 1.381(14) . ?
C13 H13 0.9500 . ?
C13 C14 1.363(17) . ?
C14 C15 1.388(17) . ?
C14 N4 1.472(13) . ?
C15 H15 0.9500 . ?
C15 C16 1.315(15) . ?
C16 Br3 1.928(11) . ?
N4 O3 1.240(8) . ?
N4 O4 1.244(8) . ?
C9A C10A 1.39(2) . ?
C9A B2A 1.54(2) . ?
C9A Br4A 1.90(2) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.40(2) . ?
C11A C12A 1.38(3) . ?
C11A N4A 1.472(17) . ?
C12A H12A 0.9500 . ?
C12A N3A 1.39(2) . ?
B2A N3A 1.44(2) . ?
B2A C16A 1.54(2) . ?
N3A C13A 1.38(2) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.37(3) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.39(3) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.32(3) . ?
C16A Br3A 1.92(2) . ?
N4A O3A 1.242(9) . ?
N4A O4A 1.242(7) . ?
C17 C18 1.35(2) . ?
C17 B3 1.525(18) . ?
C17 Br6 1.914(10) . ?
C18 H18 0.9500 . ?
C18 C19 1.437(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.340(19) . ?
C20 H20 0.9500 . ?
C20 N5 1.393(17) . ?
B3 N5 1.487(14) . ?
B3 C24 1.519(16) . ?
N5 C21 1.370(15) . ?
C21 H21 0.9500 . ?
C21 C22 1.368(17) . ?
C22 C23 1.406(16) . ?
C22 N6 1.459(14) . ?
C23 H23 0.9500 . ?
C23 C24 1.361(15) . ?
C24 Br5 1.902(10) . ?
N6 O5 1.183(14) . ?
N6 O6 1.224(15) . ?
C17A C18A 1.35(3) . ?
C17A B3A 1.53(3) . ?
C17A Br6A 1.91(2) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.44(3) . ?
C19A C20A 1.34(3) . ?
C19A N6A 1.47(2) . ?
C20A H20A 0.9500 . ?
C20A N5A 1.40(3) . ?
B3A N5A 1.49(2) . ?
B3A C24A 1.52(3) . ?
N5A C21A 1.38(2) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.37(3) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.41(3) . ?
C23A H23A 0.9500 . ?
C23A C24A 1.37(2) . ?
C24A Br5A 1.90(2) . ?
N6A O5A 1.2529 . ?
N6A O6A 1.2432 . ?
C1 C2 1.324(19) . ?
C1 B1 1.566(17) . ?
C1 Br1 1.904(12) . ?
C2 H2 0.9500 . ?
C2 C3 1.442(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.339(18) . ?
C4 H4 0.9500 . ?
C4 N1 1.402(14) . ?
B1 N1 1.466(15) . ?
B1 C8 1.528(17) . ?
N1 C5 1.355(14) . ?
C5 H5 0.9500 . ?
C5 C6 1.353(16) . ?
C6 C7 1.404(16) . ?
C6 N2 1.484(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.374(16) . ?
C8 Br2 1.886(11) . ?
N2 O1 1.234(15) . ?
N2 O2 1.205(14) . ?
C1A C2A 1.32(3) . ?
C1A B1A 1.57(2) . ?
C1A Br1A 1.90(2) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.44(3) . ?
C3A C4A 1.35(3) . ?
C3A N2A 1.484(18) . ?
C4A H4A 0.9500 . ?
C4A N1A 1.40(2) . ?
B1A N1A 1.47(2) . ?
B1A C8A 1.53(3) . ?
N1A C5A 1.36(2) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.36(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.41(3) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.38(3) . ?
C8A Br2A 1.89(2) . ?
N2A O1A 1.49(16) . ?
N2A O2A 1.53(13) . ?

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
C10 C9 B2 119.3(10) . . ?
C10 C9 Br4 115.3(9) . . ?
B2 C9 Br4 125.3(8) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(13) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 118.6 . . ?
C12 C11 C10 122.8(11) . . ?
C12 C11 H11 118.6 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 N3 119.4(11) . . ?
N3 C12 H12 120.3 . . ?
C9 B2 C16 131.3(10) . . ?
N3 B2 C9 114.6(10) . . ?
N3 B2 C16 114.0(9) . . ?
C12 N3 B2 123.5(10) . . ?
C13 N3 C12 115.1(10) . . ?
C13 N3 B2 121.4(9) . . ?
N3 C13 H13 120.3 . . ?
C14 C13 N3 119.4(10) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 124.3(10) . . ?
C13 C14 N4 116.4(9) . . ?
C15 C14 N4 119.3(10) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 119.1(11) . . ?
C16 C15 H15 120.5 . . ?
B2 C16 Br3 121.6(8) . . ?
C15 C16 B2 121.7(10) . . ?
C15 C16 Br3 116.5(9) . . ?
O3 N4 C14 118.2(9) . . ?
O3 N4 O4 122.6(10) . . ?
O4 N4 C14 119.2(8) . . ?
C10A C9A B2A 119(2) . . ?
C10A C9A Br4A 114(2) . . ?
B2A C9A Br4A 127(2) . . ?
C9A C10A H10A 120.2 . . ?
C9A C10A C11A 120(3) . . ?
C11A C10A H10A 120.2 . . ?
C10A C11A N4A 116(5) . . ?
C12A C11A C10A 123(3) . . ?
C12A C11A N4A 119(5) . . ?
C11A C12A H12A 120.7 . . ?
C11A C12A N3A 119(3) . . ?
N3A C12A H12A 120.7 . . ?
C9A B2A C16A 132(3) . . ?
N3A B2A C9A 115(3) . . ?
N3A B2A C16A 113(2) . . ?
C12A N3A B2A 123(3) . . ?
C13A N3A C12A 115(3) . . ?
C13A N3A B2A 122(3) . . ?
N3A C13A H13A 120.6 . . ?
C14A C13A N3A 119(3) . . ?
C14A C13A H13A 120.6 . . ?
C13A C14A H14A 118.8 . . ?
C13A C14A C15A 122(3) . . ?
C15A C14A H14A 118.8 . . ?
C14A C15A H15A 120.8 . . ?
C16A C15A C14A 118(3) . . ?
C16A C15A H15A 120.8 . . ?
B2A C16A Br3A 121(2) . . ?
C15A C16A B2A 121(3) . . ?
C15A C16A Br3A 116(3) . . ?
O3A N4A C11A 124(8) . . ?
O4A N4A C11A 128(8) . . ?
O4A N4A O3A 108(9) . . ?
C18 C17 B3 121.5(11) . . ?
C18 C17 Br6 115.7(10) . . ?
B3 C17 Br6 122.8(8) . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.1(15) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.5(13) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 118.8 . . ?
C19 C20 N5 122.4(11) . . ?
N5 C20 H20 118.8 . . ?
N5 B3 C17 112.9(10) . . ?
N5 B3 C24 113.1(10) . . ?
C24 B3 C17 134.0(9) . . ?
C20 N5 B3 121.5(10) . . ?
C21 N5 C20 116.4(9) . . ?
C21 N5 B3 122.1(10) . . ?
N5 C21 H21 119.7 . . ?
C22 C21 N5 120.5(10) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C23 123.0(10) . . ?
C21 C22 N6 118.3(10) . . ?
C23 C22 N6 118.8(10) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 C22 119.5(10) . . ?
C24 C23 H23 120.3 . . ?
B3 C24 Br5 121.9(8) . . ?
C23 C24 B3 121.8(9) . . ?
C23 C24 Br5 116.2(8) . . ?
O5 N6 C22 119.1(10) . . ?
O5 N6 O6 122.6(11) . . ?
O6 N6 C22 118.4(10) . . ?
C18A C17A B3A 123(2) . . ?
C18A C17A Br6A 116(2) . . ?
B3A C17A Br6A 122(2) . . ?
C17A C18A H18A 119.5 . . ?
C17A C18A C19A 121(3) . . ?
C19A C18A H18A 119.5 . . ?
C18A C19A N6A 124(4) . . ?
C20A C19A C18A 119(3) . . ?
C20A C19A N6A 116(4) . . ?
C19A C20A H20A 118.2 . . ?
C19A C20A N5A 124(3) . . ?
N5A C20A H20A 118.2 . . ?
N5A B3A C17A 112(2) . . ?
N5A B3A C24A 114(3) . . ?
C24A B3A C17A 134(3) . . ?
C20A N5A B3A 120(3) . . ?
C21A N5A C20A 115(3) . . ?
C21A N5A B3A 121(3) . . ?
N5A C21A H21A 120.5 . . ?
C22A C21A N5A 119(3) . . ?
C22A C21A H21A 120.5 . . ?
C21A C22A H22A 119.0 . . ?
C21A C22A C23A 122(3) . . ?
C23A C22A H22A 119.0 . . ?
C22A C23A H23A 121.0 . . ?
C24A C23A C22A 118(3) . . ?
C24A C23A H23A 121.1 . . ?
B3A C24A Br5A 123(3) . . ?
C23A C24A B3A 120(2) . . ?
C23A C24A Br5A 115(3) . . ?
O5A N6A C19A 119(7) . . ?
O6A N6A C19A 121(7) . . ?
O6A N6A O5A 119.7 . . ?
C2 C1 B1 120.2(12) . . ?
C2 C1 Br1 116.8(10) . . ?
B1 C1 Br1 122.9(8) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.9(14) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 118.6 . . ?
C4 C3 C2 122.7(12) . . ?
C4 C3 H3 118.6 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 N1 120.6(11) . . ?
N1 C4 H4 119.7 . . ?
N1 B1 C1 113.9(10) . . ?
N1 B1 C8 114.7(10) . . ?
C8 B1 C1 131.4(10) . . ?
C4 N1 B1 121.6(10) . . ?
C5 N1 C4 116.8(9) . . ?
C5 N1 B1 121.6(9) . . ?
N1 C5 H5 119.5 . . ?
C6 C5 N1 120.9(10) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 123.8(11) . . ?
C5 C6 N2 117.6(10) . . ?
C7 C6 N2 118.5(10) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.1(10) . . ?
C8 C7 H7 120.5 . . ?
B1 C8 Br2 124.3(8) . . ?
C7 C8 B1 119.9(10) . . ?
C7 C8 Br2 115.7(8) . . ?
O1 N2 C6 119.0(10) . . ?
O2 N2 C6 117.5(10) . . ?
O2 N2 O1 123.4(11) . . ?
C2A C1A B1A 121(3) . . ?
C2A C1A Br1A 118(3) . . ?
B1A C1A Br1A 121(2) . . ?
C1A C2A H2A 120.8 . . ?
C1A C2A C3A 118(3) . . ?
C3A C2A H2A 120.8 . . ?
C2A C3A N2A 122(6) . . ?
C4A C3A C2A 121(4) . . ?
C4A C3A N2A 110(6) . . ?
C3A C4A H4A 120.3 . . ?
C3A C4A N1A 119(3) . . ?
N1A C4A H4A 120.3 . . ?
N1A B1A C1A 113(2) . . ?
N1A B1A C8A 115(2) . . ?
C8A B1A C1A 131(3) . . ?
C4A N1A B1A 122(2) . . ?
C5A N1A C4A 117(3) . . ?
C5A N1A B1A 121(2) . . ?
N1A C5A H5A 120.0 . . ?
N1A C5A C6A 120(3) . . ?
C6A C5A H5A 120.0 . . ?
C5A C6A H6A 119.3 . . ?
C5A C6A C7A 121(3) . . ?
C7A C6A H6A 119.3 . . ?
C6A C7A H7A 121.1 . . ?
C8A C7A C6A 118(3) . . ?
C8A C7A H7A 121.1 . . ?
B1A C8A Br2A 127(2) . . ?
C7A C8A B1A 117(3) . . ?
C7A C8A Br2A 115(2) . . ?
C3A N2A O2A 124(8) . . ?
O1A N2A C3A 124(9) . . ?
O1A N2A O2A 112(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C10 C11 C12 -2(2) . . . . ?
C9 B2 N3 C12 -3(2) . . . . ?
C9 B2 N3 C13 176.9(12) . . . . ?
C9 B2 C16 C15 -178.6(15) . . . . ?
C9 B2 C16 Br3 6(2) . . . . ?
C10 C9 B2 N3 4(2) . . . . ?
C10 C9 B2 C16 -178.2(15) . . . . ?
C10 C11 C12 N3 3(2) . . . . ?
C11 C12 N3 B2 0(2) . . . . ?
C11 C12 N3 C13 179.9(13) . . . . ?
C12 N3 C13 C14 -179.2(13) . . . . ?
B2 C9 C10 C11 -1.7(19) . . . . ?
B2 N3 C13 C14 1(2) . . . . ?
N3 B2 C16 C15 -1(2) . . . . ?
N3 B2 C16 Br3 -175.7(10) . . . . ?
N3 C13 C14 C15 1(2) . . . . ?
N3 C13 C14 N4 -179.1(11) . . . . ?
C13 C14 C15 C16 -3.3(19) . . . . ?
C13 C14 N4 O3 -171.6(13) . . . . ?
C13 C14 N4 O4 9.8(17) . . . . ?
C14 C15 C16 B2 2.8(19) . . . . ?
C14 C15 C16 Br3 178.2(8) . . . . ?
C15 C14 N4 O3 8.1(17) . . . . ?
C15 C14 N4 O4 -170.6(11) . . . . ?
C16 B2 N3 C12 178.9(13) . . . . ?
C16 B2 N3 C13 -1(2) . . . . ?
Br4 C9 C10 C11 176.9(10) . . . . ?
Br4 C9 B2 N3 -174.8(10) . . . . ?
Br4 C9 B2 C16 3(2) . . . . ?
N4 C14 C15 C16 177.0(10) . . . . ?
C9A C10A C11A C12A -11(26) . . . . ?
C9A C10A C11A N4A -171(16) . . . . ?
C9A B2A N3A C12A 10(24) . . . . ?
C9A B2A N3A C13A -169(14) . . . . ?
C9A B2A C16A C15A 161(19) . . . . ?
C9A B2A C16A Br3A -4(26) . . . . ?
C10A C9A B2A N3A -4(25) . . . . ?
C10A C9A B2A C16A -175(19) . . . . ?
C10A C11A C12A N3A 17(22) . . . . ?
C10A C11A N4A O3A 151(15) . . . . ?
C10A C11A N4A O4A -30(19) . . . . ?
C11A C12A N3A B2A -17(23) . . . . ?
C11A C12A N3A C13A 163(14) . . . . ?
C12A C11A N4A O3A -10(19) . . . . ?
C12A C11A N4A O4A 169(14) . . . . ?
C12A N3A C13A C14A 173(13) . . . . ?
B2A C9A C10A C11A 4(27) . . . . ?
B2A N3A C13A C14A -8(22) . . . . ?
N3A B2A C16A C15A -10(20) . . . . ?
N3A B2A C16A Br3A -176(11) . . . . ?
N3A C13A C14A C15A 17(20) . . . . ?
C13A C14A C15A C16A -24(18) . . . . ?
C14A C15A C16A B2A 19(17) . . . . ?
C14A C15A C16A Br3A -174(9) . . . . ?
C16A B2A N3A C12A -177(14) . . . . ?
C16A B2A N3A C13A 4(22) . . . . ?
Br4A C9A C10A C11A -174(14) . . . . ?
Br4A C9A B2A N3A 174(11) . . . . ?
Br4A C9A B2A C16A 3(29) . . . . ?
N4A C11A C12A N3A 176(13) . . . . ?
C17 C18 C19 C20 3(2) . . . . ?
C17 B3 N5 C20 -2(2) . . . . ?
C17 B3 N5 C21 -179.4(11) . . . . ?
C17 B3 C24 C23 178.5(17) . . . . ?
C17 B3 C24 Br5 1(3) . . . . ?
C18 C17 B3 N5 2(2) . . . . ?
C18 C17 B3 C24 -176.8(17) . . . . ?
C18 C19 C20 N5 -2(2) . . . . ?
C19 C20 N5 B3 2(2) . . . . ?
C19 C20 N5 C21 179.7(12) . . . . ?
C20 N5 C21 C22 -176.5(11) . . . . ?
B3 C17 C18 C19 -3(2) . . . . ?
B3 N5 C21 C22 0.8(18) . . . . ?
N5 B3 C24 C23 -1(2) . . . . ?
N5 B3 C24 Br5 -178.1(9) . . . . ?
N5 C21 C22 C23 -0.9(18) . . . . ?
N5 C21 C22 N6 178.6(10) . . . . ?
C21 C22 C23 C24 0.1(19) . . . . ?
C21 C22 N6 O5 -165.8(12) . . . . ?
C21 C22 N6 O6 13.4(17) . . . . ?
C22 C23 C24 B3 0.8(19) . . . . ?
C22 C23 C24 Br5 178.2(9) . . . . ?
C23 C22 N6 O5 13.7(18) . . . . ?
C23 C22 N6 O6 -167.2(12) . . . . ?
C24 B3 N5 C20 177.1(12) . . . . ?
C24 B3 N5 C21 0(2) . . . . ?
Br6 C17 C18 C19 176.9(11) . . . . ?
Br6 C17 B3 N5 -177.0(9) . . . . ?
Br6 C17 B3 C24 4(3) . . . . ?
N6 C22 C23 C24 -179.3(11) . . . . ?
C17A C18A C19A C20A 1(28) . . . . ?
C17A C18A C19A N6A -177(15) . . . . ?
C17A B3A N5A C20A 13(20) . . . . ?
C17A B3A N5A C21A 171(14) . . . . ?
C17A B3A C24A C23A 175(19) . . . . ?
C17A B3A C24A Br5A -21(26) . . . . ?
C18A C17A B3A N5A -6(25) . . . . ?
C18A C17A B3A C24A -174(20) . . . . ?
C18A C19A C20A N5A 8(25) . . . . ?
C18A C19A N6A O5A -169(15) . . . . ?
C18A C19A N6A O6A 11(22) . . . . ?
C19A C20A N5A B3A -15(21) . . . . ?
C19A C20A N5A C21A -174(16) . . . . ?
C20A C19A N6A O5A 13(19) . . . . ?
C20A C19A N6A O6A -167(14) . . . . ?
C20A N5A C21A C22A 165(14) . . . . ?
B3A C17A C18A C19A -1(29) . . . . ?
B3A N5A C21A C22A 6(20) . . . . ?
N5A B3A C24A C23A 7(19) . . . . ?
N5A B3A C24A Br5A 171(10) . . . . ?
N5A C21A C22A C23A 19(19) . . . . ?
C21A C22A C23A C24A -29(15) . . . . ?
C22A C23A C24A B3A 15(15) . . . . ?
C22A C23A C24A Br5A -150(9) . . . . ?
C24A B3A N5A C20A -176(13) . . . . ?
C24A B3A N5A C21A -18(20) . . . . ?
Br6A C17A C18A C19A 179(14) . . . . ?
Br6A C17A B3A N5A 174(11) . . . . ?
Br6A C17A B3A C24A 6(28) . . . . ?
N6A C19A C20A N5A -174(13) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C1 B1 N1 C4 0.2(18) . . . . ?
C1 B1 N1 C5 178.9(11) . . . . ?
C1 B1 C8 C7 -178.9(13) . . . . ?
C1 B1 C8 Br2 1(2) . . . . ?
C2 C1 B1 N1 -1.4(19) . . . . ?
C2 C1 B1 C8 178.8(14) . . . . ?
C2 C3 C4 N1 -2(2) . . . . ?
C3 C4 N1 B1 1(2) . . . . ?
C3 C4 N1 C5 -177.4(13) . . . . ?
C4 N1 C5 C6 -179.8(13) . . . . ?
B1 C1 C2 C3 1(2) . . . . ?
B1 N1 C5 C6 1.4(19) . . . . ?
N1 B1 C8 C7 1.3(18) . . . . ?
N1 B1 C8 Br2 -178.5(9) . . . . ?
N1 C5 C6 C7 -1(2) . . . . ?
N1 C5 C6 N2 -177.4(11) . . . . ?
C5 C6 C7 C8 1(2) . . . . ?
C5 C6 N2 O1 -9.8(18) . . . . ?
C5 C6 N2 O2 169.0(13) . . . . ?
C6 C7 C8 B1 -1.3(19) . . . . ?
C6 C7 C8 Br2 178.5(10) . . . . ?
C7 C6 N2 O1 174.0(12) . . . . ?
C7 C6 N2 O2 -7.2(18) . . . . ?
C8 B1 N1 C4 180.0(12) . . . . ?
C8 B1 N1 C5 -1.3(18) . . . . ?
Br1 C1 C2 C3 178.6(10) . . . . ?
Br1 C1 B1 N1 -178.7(9) . . . . ?
Br1 C1 B1 C8 2(2) . . . . ?
N2 C6 C7 C8 177.3(11) . . . . ?
C1A C2A C3A C4A -30(17) . . . . ?
C1A C2A C3A N2A -178(13) . . . . ?
C1A B1A N1A C4A -7(18) . . . . ?
C1A B1A N1A C5A 177(12) . . . . ?
C1A B1A C8A C7A -157(14) . . . . ?
C1A B1A C8A Br2A 12(20) . . . . ?
C2A C1A B1A N1A 1(19) . . . . ?
C2A C1A B1A C8A 169(15) . . . . ?
C2A C3A C4A N1A 24(18) . . . . ?
C2A C3A N2A O1A 159(12) . . . . ?
C2A C3A N2A O2A -15(16) . . . . ?
C3A C4A N1A B1A -5(21) . . . . ?
C3A C4A N1A C5A 170(13) . . . . ?
C4A C3A N2A O1A 8(16) . . . . ?
C4A C3A N2A O2A -166(11) . . . . ?
C4A N1A C5A C6A 178(13) . . . . ?
B1A C1A C2A C3A 16(20) . . . . ?
B1A N1A C5A C6A -6(21) . . . . ?
N1A B1A C8A C7A 10(15) . . . . ?
N1A B1A C8A Br2A 179(9) . . . . ?
N1A C5A C6A C7A -14(19) . . . . ?
C5A C6A C7A C8A 33(14) . . . . ?
C6A C7A C8A B1A -29(12) . . . . ?
C6A C7A C8A Br2A 161(8) . . . . ?
C8A B1A N1A C4A -177(12) . . . . ?
C8A B1A N1A C5A 8(19) . . . . ?
Br1A C1A C2A C3A -171(10) . . . . ?
Br1A C1A B1A N1A -171(9) . . . . ?
Br1A C1A B1A C8A -3(20) . . . . ?
N2A C3A C4A N1A 176(13) . . . . ?

####################################################################### 
# 
# 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_fang230328b_a
_database_code_depnum_ccdc_archive 'CCDC 2290090'
loop_
_audit_author_name
_audit_author_address
'Xiangdong Fang'
;Tongji University
China
;
_audit_update_record             
;
2023-08-22 deposited with the CCDC.	2023-09-27 downloaded from the CCDC.
;
_audit_creation_date             2023-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C8 H5 B I2 N2 O2)'
_chemical_formula_sum            'C16 H10 B2 I4 N4 O4'
_chemical_formula_weight         851.50
_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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.8145(7)
_cell_length_b                   8.1585(7)
_cell_length_c                   17.1814(15)
_cell_angle_alpha                82.588(3)
_cell_angle_beta                 89.880(3)
_cell_angle_gamma                85.833(3)
_cell_volume                     1083.34(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8884
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.377
_cell_measurement_theta_min      2.614
_shelx_estimated_absorpt_T_max   0.655
_shelx_estimated_absorpt_T_min   0.458
_exptl_absorpt_coefficient_mu    5.784
_exptl_absorpt_correction_T_max  0.2590
_exptl_absorpt_correction_T_min  0.1906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0901 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.7359.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16757
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.397
_diffrn_reflns_theta_min         2.650
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-III CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3261
_reflns_number_total             3980
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.591
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.187
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0110P)²+8.1145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0762
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15)
;
_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
I2 I 0.64341(7) 0.20062(6) 0.37601(3) 0.02777(14) Uani 1 1 d . . . . .
I1 I 0.87732(7) 0.55582(7) 0.28342(3) 0.02817(14) Uani 1 1 d . . . . .
I3 I 0.90487(6) 0.36106(6) 0.93322(3) 0.02446(13) Uani 1 1 d . . . . .
I4 I 0.74472(6) 0.23381(6) 1.13548(3) 0.02740(14) Uani 1 1 d . . . . .
O1 O 0.6038(6) 0.3181(7) 0.7447(3) 0.0262(12) Uani 1 1 d . . . . .
O2 O 0.5196(7) 0.1178(7) 0.6870(3) 0.0312(13) Uani 1 1 d . . . . .
O3 O 0.8800(7) -0.0324(7) 0.7078(3) 0.0297(13) Uani 1 1 d . . . . .
O4 O 0.7580(7) -0.2573(6) 0.7460(3) 0.0294(13) Uani 1 1 d . . . . .
N1 N 0.7607(7) 0.5630(7) 0.5416(3) 0.0141(12) Uani 1 1 d . . . . .
N2 N 0.5855(8) 0.2502(8) 0.6860(4) 0.0231(14) Uani 1 1 d . . . . .
N3 N 0.7005(7) -0.1475(7) 0.9671(3) 0.0143(12) Uani 1 1 d . . . . .
N4 N 0.8124(8) -0.1248(7) 0.7583(3) 0.0210(14) Uani 1 1 d . . . . .
C1 C 0.8292(9) 0.6124(9) 0.3985(4) 0.0208(16) Uani 1 1 d . . . . .
C2 C 0.8738(9) 0.7637(9) 0.4097(4) 0.0207(16) Uani 1 1 d . . . . .
H2 H 0.913566 0.835785 0.366615 0.025 Uiso 1 1 calc R U . . .
C3 C 0.8621(10) 0.8175(10) 0.4855(5) 0.031(2) Uani 1 1 d . . . . .
H3 H 0.891642 0.926629 0.490478 0.037 Uiso 1 1 calc R U . . .
C4 C 0.8139(9) 0.7269(10) 0.5475(4) 0.0229(17) Uani 1 1 d . . . . .
H4 H 0.813402 0.767631 0.596859 0.027 Uiso 1 1 calc R U . . .
C5 C 0.7053(8) 0.4804(8) 0.6107(4) 0.0172(15) Uani 1 1 d . . . . .
H5 H 0.709620 0.528775 0.658002 0.021 Uiso 1 1 calc R U . . .
C6 C 0.6441(9) 0.3288(8) 0.6107(4) 0.0157(15) Uani 1 1 d . . . . .
C7 C 0.6294(9) 0.2513(9) 0.5426(4) 0.0196(16) Uani 1 1 d . . . . .
H7 H 0.580947 0.147170 0.545726 0.024 Uiso 1 1 calc R U . . .
C8 C 0.6845(9) 0.3254(9) 0.4725(4) 0.0167(15) Uani 1 1 d . . . . .
C9 C 0.7085(9) 0.0243(9) 1.0777(4) 0.0182(15) Uani 1 1 d . . . . .
C10 C 0.6413(9) -0.1014(9) 1.1252(4) 0.0183(16) Uani 1 1 d . . . . .
H10 H 0.618991 -0.090918 1.178726 0.022 Uiso 1 1 calc R U . . .
C11 C 0.6043(8) -0.2502(9) 1.0938(4) 0.0194(16) Uani 1 1 d . . . . .
H11 H 0.558799 -0.337338 1.127822 0.023 Uiso 1 1 calc R U . . .
C12 C 0.6306(9) -0.2704(9) 1.0207(5) 0.0227(17) Uani 1 1 d . . . . .
H12 H 0.602013 -0.370565 1.002973 0.027 Uiso 1 1 calc R U . . .
C13 C 0.7226(9) -0.1838(8) 0.8915(4) 0.0194(16) Uani 1 1 d . . . . .
H13 H 0.688214 -0.285721 0.877821 0.023 Uiso 1 1 calc R U . . .
C14 C 0.7924(8) -0.0760(8) 0.8370(4) 0.0151(15) Uani 1 1 d . . . . .
C15 C 0.8458(8) 0.0777(8) 0.8508(4) 0.0166(15) Uani 1 1 d . . . . .
H15 H 0.896155 0.148457 0.810186 0.020 Uiso 1 1 calc R U . . .
C16 C 0.8240(8) 0.1235(8) 0.9238(4) 0.0166(15) Uani 1 1 d . . . . .
B1 B 0.7592(9) 0.4949(10) 0.4663(4) 0.0138(16) Uani 1 1 d . . . . .
B2 B 0.7483(10) 0.0117(10) 0.9908(5) 0.0183(18) Uani 1 1 d . . . . .


_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
I2 C8 2.091(7) . ?
I1 C1 2.114(7) . ?
I3 C16 2.108(7) . ?
I4 C9 2.121(7) . ?
O1 N2 1.225(8) . ?
O2 N2 1.228(8) . ?
O3 N4 1.220(7) . ?
O4 N4 1.232(8) . ?
N1 C4 1.445(9) . ?
N1 C5 1.372(9) . ?
N1 B1 1.473(9) . ?
N2 C6 1.457(8) . ?
N3 C12 1.411(9) . ?
N3 C13 1.377(9) . ?
N3 B2 1.483(10) . ?
N4 C14 1.463(8) . ?
C1 C2 1.344(10) . ?
C1 B1 1.537(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.428(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.288(11) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.357(10) . ?
C6 C7 1.408(10) . ?
C7 H7 0.9500 . ?
C7 C8 1.361(10) . ?
C8 B1 1.530(11) . ?
C9 C10 1.361(10) . ?
C9 B2 1.539(11) . ?
C10 H10 0.9500 . ?
C10 C11 1.438(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.301(10) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.343(10) . ?
C14 C15 1.398(10) . ?
C15 H15 0.9500 . ?
C15 C16 1.361(9) . ?
C16 B2 1.521(11) . ?

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
C4 N1 B1 122.0(6) . . ?
C5 N1 C4 114.7(6) . . ?
C5 N1 B1 123.3(6) . . ?
O1 N2 O2 123.3(6) . . ?
O1 N2 C6 119.1(6) . . ?
O2 N2 C6 117.5(6) . . ?
C12 N3 B2 121.9(6) . . ?
C13 N3 C12 116.3(6) . . ?
C13 N3 B2 121.8(6) . . ?
O3 N4 O4 123.1(6) . . ?
O3 N4 C14 118.8(6) . . ?
O4 N4 C14 118.2(6) . . ?
C2 C1 I1 113.3(5) . . ?
C2 C1 B1 120.9(7) . . ?
B1 C1 I1 125.7(5) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.8(7) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 118.1 . . ?
C4 C3 C2 123.9(7) . . ?
C4 C3 H3 118.1 . . ?
N1 C4 H4 120.1 . . ?
C3 C4 N1 119.7(7) . . ?
C3 C4 H4 120.1 . . ?
N1 C5 H5 120.3 . . ?
C6 C5 N1 119.3(6) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 N2 116.0(6) . . ?
C5 C6 C7 123.6(6) . . ?
C7 C6 N2 120.3(6) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0(6) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 I2 115.5(5) . . ?
C7 C8 B1 120.6(6) . . ?
B1 C8 I2 123.8(5) . . ?
C10 C9 I4 113.1(5) . . ?
C10 C9 B2 121.9(6) . . ?
B2 C9 I4 125.1(5) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.7(6) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 118.7 . . ?
C12 C11 C10 122.7(6) . . ?
C12 C11 H11 118.7 . . ?
N3 C12 H12 119.1 . . ?
C11 C12 N3 121.8(6) . . ?
C11 C12 H12 119.1 . . ?
N3 C13 H13 119.8 . . ?
C14 C13 N3 120.4(6) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 N4 116.9(6) . . ?
C13 C14 C15 124.3(6) . . ?
C15 C14 N4 118.8(6) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.4(6) . . ?
C16 C15 H15 120.8 . . ?
C15 C16 I3 113.3(5) . . ?
C15 C16 B2 122.3(6) . . ?
B2 C16 I3 124.4(5) . . ?
N1 B1 C1 112.5(6) . . ?
N1 B1 C8 113.2(6) . . ?
C8 B1 C1 134.3(6) . . ?
N3 B2 C9 112.0(6) . . ?
N3 B2 C16 112.7(6) . . ?
C16 B2 C9 135.3(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I2 C8 B1 N1 174.8(4) . . . . ?
I2 C8 B1 C1 -3.4(11) . . . . ?
I1 C1 C2 C3 -175.3(5) . . . . ?
I1 C1 B1 N1 172.7(4) . . . . ?
I1 C1 B1 C8 -9.1(11) . . . . ?
I3 C16 B2 N3 179.2(4) . . . . ?
I3 C16 B2 C9 -0.6(12) . . . . ?
I4 C9 C10 C11 178.1(5) . . . . ?
I4 C9 B2 N3 -177.0(4) . . . . ?
I4 C9 B2 C16 2.7(12) . . . . ?
O1 N2 C6 C5 -4.4(9) . . . . ?
O1 N2 C6 C7 178.1(6) . . . . ?
O2 N2 C6 C5 175.6(6) . . . . ?
O2 N2 C6 C7 -1.9(9) . . . . ?
O3 N4 C14 C13 -177.8(6) . . . . ?
O3 N4 C14 C15 2.3(9) . . . . ?
O4 N4 C14 C13 3.0(9) . . . . ?
O4 N4 C14 C15 -176.9(6) . . . . ?
N1 C5 C6 N2 -179.2(6) . . . . ?
N1 C5 C6 C7 -1.8(10) . . . . ?
N2 C6 C7 C8 -180.0(6) . . . . ?
N3 C13 C14 N4 179.6(6) . . . . ?
N3 C13 C14 C15 -0.6(11) . . . . ?
N4 C14 C15 C16 178.9(6) . . . . ?
C1 C2 C3 C4 1.8(12) . . . . ?
C2 C1 B1 N1 -4.2(9) . . . . ?
C2 C1 B1 C8 174.0(7) . . . . ?
C2 C3 C4 N1 -2.7(11) . . . . ?
C4 N1 C5 C6 176.6(6) . . . . ?
C4 N1 B1 C1 3.3(9) . . . . ?
C4 N1 B1 C8 -175.2(6) . . . . ?
C5 N1 C4 C3 -177.4(7) . . . . ?
C5 N1 B1 C1 -179.6(6) . . . . ?
C5 N1 B1 C8 1.8(9) . . . . ?
C5 C6 C7 C8 2.8(11) . . . . ?
C6 C7 C8 I2 -177.2(5) . . . . ?
C6 C7 C8 B1 -1.3(10) . . . . ?
C7 C8 B1 N1 -0.8(9) . . . . ?
C7 C8 B1 C1 -179.0(7) . . . . ?
C9 C10 C11 C12 -0.8(10) . . . . ?
C10 C9 B2 N3 1.5(9) . . . . ?
C10 C9 B2 C16 -178.7(8) . . . . ?
C10 C11 C12 N3 1.1(10) . . . . ?
C12 N3 C13 C14 -178.3(6) . . . . ?
C12 N3 B2 C9 -1.3(9) . . . . ?
C12 N3 B2 C16 178.9(6) . . . . ?
C13 N3 C12 C11 179.8(6) . . . . ?
C13 N3 B2 C9 179.0(6) . . . . ?
C13 N3 B2 C16 -0.8(9) . . . . ?
C13 C14 C15 C16 -1.0(10) . . . . ?
C14 C15 C16 I3 -178.3(5) . . . . ?
C14 C15 C16 B2 1.6(10) . . . . ?
C15 C16 B2 N3 -0.7(9) . . . . ?
C15 C16 B2 C9 179.5(7) . . . . ?
B1 N1 C4 C3 -0.1(10) . . . . ?
B1 N1 C5 C6 -0.6(10) . . . . ?
B1 C1 C2 C3 1.9(11) . . . . ?
B2 N3 C12 C11 0.1(10) . . . . ?
B2 N3 C13 C14 1.5(10) . . . . ?
B2 C9 C10 C11 -0.6(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive,Photo-sensitive
