# Supplementary Information (SI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_mo211029a
_database_code_depnum_ccdc_archive 'CCDC 2202487'
loop_
_audit_author_name
_audit_author_address
BODIPY-X
;Hangzhou Normal University
China
;
_audit_update_record             
;
2022-08-20 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;
_audit_creation_date             2021-10-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H19 B F2 I2 N2 O2'
_chemical_formula_sum            'C28 H19 B F2 I2 N2 O2'
_chemical_formula_weight         718.06
_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'
F F 0.0171 0.0103 '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                   9.6753(16)
_cell_length_b                   12.238(2)
_cell_length_c                   13.120(2)
_cell_angle_alpha                64.097(3)
_cell_angle_beta                 81.872(3)
_cell_angle_gamma                71.312(3)
_cell_volume                     1323.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4764
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.489
_cell_measurement_theta_min      2.486
_shelx_estimated_absorpt_T_max   0.760
_shelx_estimated_absorpt_T_min   0.713
_exptl_absorpt_coefficient_mu    2.418
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0643 before and 0.0353 after correction.
The Ratio of minimum to maximum transmission is 0.8625.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.801
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13423
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.584
_diffrn_reflns_theta_min         1.725
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.842
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4913
_reflns_number_total             6843
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         1.420
_refine_diff_density_min         -1.486
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         6843
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.038
_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)+(0.0360P)²+1.4516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.1017
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C11(H11), C12(H12), C14(H14), C16(H16), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 0.82399(3) 0.65931(3) 0.55574(3) 0.06546(11) Uani 1 1 d . . . . .
I2 I 0.20834(3) 0.53875(3) 0.00235(3) 0.07543(12) Uani 1 1 d . . . . .
F2 F 0.3901(3) 0.8435(2) 0.1851(2) 0.0833(9) Uani 1 1 d . . . . .
F3 F 0.2606(2) 0.7525(3) 0.3403(3) 0.0788(8) Uani 1 1 d . . . . .
O1 O 0.5058(3) 0.8283(2) 0.4055(2) 0.0501(6) Uani 1 1 d . . . . .
O2 O 0.1744(3) 0.7723(2) 0.1113(3) 0.0630(8) Uani 1 1 d . . . . .
N1 N 0.5222(3) 0.6675(2) 0.3458(2) 0.0377(6) Uani 1 1 d . . . . .
N2 N 0.3731(3) 0.6385(2) 0.2259(2) 0.0414(6) Uani 1 1 d . . . . .
C1 C 0.5758(4) 0.7147(3) 0.4021(3) 0.0405(7) Uani 1 1 d . . . . .
C2 C 0.7004(4) 0.6256(3) 0.4630(3) 0.0429(7) Uani 1 1 d . . . . .
C3 C 0.7250(3) 0.5186(3) 0.4432(3) 0.0407(7) Uani 1 1 d . . . . .
H3 H 0.799960 0.443399 0.473429 0.049 Uiso 1 1 calc R U . . .
C4 C 0.6154(3) 0.5450(3) 0.3687(3) 0.0363(6) Uani 1 1 d . . . . .
C5 C 0.5947(3) 0.4728(3) 0.3164(3) 0.0358(6) Uani 1 1 d . . . . .
C6 C 0.4757(3) 0.5210(3) 0.2447(3) 0.0372(7) Uani 1 1 d . . . . .
C7 C 0.4374(3) 0.4720(3) 0.1765(3) 0.0418(7) Uani 1 1 d . . . . .
H7 H 0.487921 0.395597 0.171934 0.050 Uiso 1 1 calc R U . . .
C8 C 0.3126(4) 0.5568(3) 0.1185(3) 0.0455(8) Uani 1 1 d . . . . .
C9 C 0.2771(4) 0.6591(3) 0.1508(3) 0.0452(8) Uani 1 1 d . . . . .
C10 C 0.7022(3) 0.3494(3) 0.3305(3) 0.0368(6) Uani 1 1 d . . . . .
C11 C 0.8499(4) 0.3391(3) 0.3084(3) 0.0448(8) Uani 1 1 d . . . . .
H11 H 0.883788 0.408446 0.290401 0.054 Uiso 1 1 calc R U . . .
C12 C 0.9465(4) 0.2249(4) 0.3135(3) 0.0512(9) Uani 1 1 d . . . . .
H12 H 1.044447 0.219719 0.296891 0.061 Uiso 1 1 calc R U . . .
C13 C 0.9007(4) 0.1181(3) 0.3427(3) 0.0493(8) Uani 1 1 d . . . . .
C14 C 0.7544(4) 0.1293(3) 0.3662(3) 0.0492(8) Uani 1 1 d . . . . .
H14 H 0.721418 0.058945 0.386614 0.059 Uiso 1 1 calc R U . . .
C15 C 1.0073(5) -0.0063(4) 0.3489(4) 0.0702(12) Uani 1 1 d . . . . .
H15A H 1.091202 0.009929 0.303055 0.105 Uiso 1 1 calc R U . . .
H15B H 0.961061 -0.046978 0.321493 0.105 Uiso 1 1 calc R U . . .
H15C H 1.037060 -0.060600 0.426059 0.105 Uiso 1 1 calc R U . . .
C16 C 0.6556(4) 0.2423(3) 0.3603(3) 0.0437(7) Uani 1 1 d . . . . .
H16 H 0.557604 0.247035 0.376221 0.052 Uiso 1 1 calc R U . . .
C17 C 0.5168(4) 0.9407(3) 0.3138(3) 0.0422(7) Uani 1 1 d . . . . .
C18 C 0.4129(4) 1.0492(3) 0.3104(4) 0.0532(9) Uani 1 1 d . . . . .
H18 H 0.341915 1.045591 0.366540 0.064 Uiso 1 1 calc R U . . .
C19 C 0.4155(5) 1.1633(4) 0.2227(4) 0.0649(11) Uani 1 1 d . . . . .
H19 H 0.345042 1.237369 0.219104 0.078 Uiso 1 1 calc R U . . .
C20 C 0.5214(5) 1.1692(4) 0.1401(4) 0.0668(12) Uani 1 1 d . . . . .
H20 H 0.522337 1.246808 0.080872 0.080 Uiso 1 1 calc R U . . .
C21 C 0.6240(5) 1.0614(4) 0.1454(4) 0.0675(12) Uani 1 1 d . . . . .
H21 H 0.694910 1.065373 0.089113 0.081 Uiso 1 1 calc R U . . .
C22 C 0.6248(5) 0.9444(4) 0.2340(4) 0.0603(10) Uani 1 1 d . . . . .
H22 H 0.697069 0.870717 0.238804 0.072 Uiso 1 1 calc R U . . .
C23 C 0.0352(4) 0.7757(3) 0.0883(3) 0.0443(8) Uani 1 1 d . . . . .
C24 C -0.0369(4) 0.6955(4) 0.1657(3) 0.0559(9) Uani 1 1 d . . . . .
H24 H 0.006077 0.635277 0.234845 0.067 Uiso 1 1 calc R U . . .
C25 C -0.1741(5) 0.7049(4) 0.1400(4) 0.0687(12) Uani 1 1 d . . . . .
H25 H -0.223290 0.648695 0.191115 0.082 Uiso 1 1 calc R U . . .
C26 C -0.2385(4) 0.7953(5) 0.0408(5) 0.0721(13) Uani 1 1 d . . . . .
H26 H -0.331906 0.801404 0.024682 0.086 Uiso 1 1 calc R U . . .
C27 C -0.1673(5) 0.8774(4) -0.0354(4) 0.0687(12) Uani 1 1 d . . . . .
H27 H -0.212413 0.939868 -0.103023 0.082 Uiso 1 1 calc R U . . .
C28 C -0.0271(4) 0.8677(4) -0.0121(3) 0.0571(10) Uani 1 1 d . . . . .
H28 H 0.023118 0.922580 -0.063719 0.069 Uiso 1 1 calc R U . . .
B1 B 0.3798(4) 0.7334(4) 0.2733(4) 0.0494(10) 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 C2 2.060(3) . ?
I2 C8 2.063(3) . ?
F2 B1 1.362(5) . ?
F3 B1 1.370(5) . ?
O1 C1 1.355(4) . ?
O1 C17 1.402(4) . ?
O2 C9 1.346(4) . ?
O2 C23 1.405(4) . ?
N1 C1 1.349(4) . ?
N1 C4 1.402(4) . ?
N1 B1 1.563(5) . ?
N2 C6 1.400(4) . ?
N2 C9 1.338(4) . ?
N2 B1 1.558(5) . ?
C1 C2 1.397(5) . ?
C2 C3 1.386(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.408(4) . ?
C4 C5 1.406(4) . ?
C5 C6 1.395(4) . ?
C5 C10 1.483(4) . ?
C6 C7 1.415(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.372(5) . ?
C8 C9 1.419(5) . ?
C10 C11 1.394(4) . ?
C10 C16 1.399(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.392(5) . ?
C13 C14 1.381(5) . ?
C13 C15 1.516(5) . ?
C14 H14 0.9300 . ?
C14 C16 1.383(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C17 C18 1.371(5) . ?
C17 C22 1.367(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.353(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.394(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.360(5) . ?
C23 C28 1.364(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.373(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.355(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.362(7) . ?
C27 H27 0.9300 . ?
C27 C28 1.389(6) . ?
C28 H28 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C17 120.0(3) . . ?
C9 O2 C23 118.1(3) . . ?
C1 N1 C4 106.9(2) . . ?
C1 N1 B1 126.9(3) . . ?
C4 N1 B1 126.2(3) . . ?
C6 N2 B1 126.2(3) . . ?
C9 N2 C6 106.9(3) . . ?
C9 N2 B1 126.6(3) . . ?
O1 C1 C2 126.5(3) . . ?
N1 C1 O1 122.5(3) . . ?
N1 C1 C2 110.6(3) . . ?
C1 C2 I1 124.1(2) . . ?
C3 C2 I1 128.8(2) . . ?
C3 C2 C1 107.0(3) . . ?
C2 C3 H3 126.4 . . ?
C2 C3 C4 107.2(3) . . ?
C4 C3 H3 126.4 . . ?
N1 C4 C3 108.3(3) . . ?
N1 C4 C5 121.1(3) . . ?
C5 C4 C3 130.6(3) . . ?
C4 C5 C10 121.2(3) . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 C10 119.2(3) . . ?
N2 C6 C7 108.0(3) . . ?
C5 C6 N2 121.6(3) . . ?
C5 C6 C7 130.3(3) . . ?
C6 C7 H7 126.0 . . ?
C8 C7 C6 108.1(3) . . ?
C8 C7 H7 126.0 . . ?
C7 C8 I2 125.7(3) . . ?
C7 C8 C9 105.9(3) . . ?
C9 C8 I2 128.4(2) . . ?
O2 C9 C8 130.6(3) . . ?
N2 C9 O2 118.0(3) . . ?
N2 C9 C8 111.2(3) . . ?
C11 C10 C5 121.0(3) . . ?
C11 C10 C16 118.6(3) . . ?
C16 C10 C5 120.3(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.8(3) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C15 121.3(4) . . ?
C14 C13 C12 117.6(3) . . ?
C14 C13 C15 121.1(4) . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C16 121.8(3) . . ?
C16 C14 H14 119.1 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16 119.8 . . ?
C14 C16 C10 120.4(3) . . ?
C14 C16 H16 119.8 . . ?
C18 C17 O1 115.3(3) . . ?
C22 C17 O1 123.2(3) . . ?
C22 C17 C18 121.5(3) . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.9(4) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.7(4) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.6(4) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.9(4) . . ?
C22 C21 H21 119.6 . . ?
C17 C22 C21 118.3(4) . . ?
C17 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
C24 C23 O2 121.2(3) . . ?
C24 C23 C28 121.8(3) . . ?
C28 C23 O2 116.9(3) . . ?
C23 C24 H24 120.6 . . ?
C23 C24 C25 118.9(4) . . ?
C25 C24 H24 120.6 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.5(4) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.5(4) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.1 . . ?
C26 C27 C28 119.9(4) . . ?
C28 C27 H27 120.1 . . ?
C23 C28 C27 118.5(4) . . ?
C23 C28 H28 120.8 . . ?
C27 C28 H28 120.8 . . ?
F2 B1 F3 112.3(3) . . ?
F2 B1 N1 109.9(3) . . ?
F2 B1 N2 109.1(3) . . ?
F3 B1 N1 110.1(3) . . ?
F3 B1 N2 110.2(3) . . ?
N2 B1 N1 105.1(2) . . ?

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 C2 C3 C4 -176.0(3) . . . . ?
I2 C8 C9 O2 -4.3(6) . . . . ?
I2 C8 C9 N2 -177.8(3) . . . . ?
O1 C1 C2 I1 -9.3(5) . . . . ?
O1 C1 C2 C3 173.7(3) . . . . ?
O1 C17 C18 C19 -179.5(3) . . . . ?
O1 C17 C22 C21 179.0(4) . . . . ?
O2 C23 C24 C25 178.5(4) . . . . ?
O2 C23 C28 C27 -177.2(4) . . . . ?
N1 C1 C2 I1 177.2(2) . . . . ?
N1 C1 C2 C3 0.1(4) . . . . ?
N1 C4 C5 C6 -3.0(5) . . . . ?
N1 C4 C5 C10 173.2(3) . . . . ?
N2 C6 C7 C8 -0.9(4) . . . . ?
C1 O1 C17 C18 162.6(3) . . . . ?
C1 O1 C17 C22 -19.0(5) . . . . ?
C1 N1 C4 C3 1.5(4) . . . . ?
C1 N1 C4 C5 -175.9(3) . . . . ?
C1 N1 B1 F2 61.4(5) . . . . ?
C1 N1 B1 F3 -62.8(4) . . . . ?
C1 N1 B1 N2 178.6(3) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 N1 -1.5(4) . . . . ?
C2 C3 C4 C5 175.6(3) . . . . ?
C3 C4 C5 C6 -179.8(3) . . . . ?
C3 C4 C5 C10 -3.6(5) . . . . ?
C4 N1 C1 O1 -174.9(3) . . . . ?
C4 N1 C1 C2 -1.0(4) . . . . ?
C4 N1 B1 F2 -121.6(3) . . . . ?
C4 N1 B1 F3 114.2(4) . . . . ?
C4 N1 B1 N2 -4.4(5) . . . . ?
C4 C5 C6 N2 -2.0(5) . . . . ?
C4 C5 C6 C7 174.8(3) . . . . ?
C4 C5 C10 C11 -52.4(5) . . . . ?
C4 C5 C10 C16 131.1(3) . . . . ?
C5 C6 C7 C8 -178.0(3) . . . . ?
C5 C10 C11 C12 -174.9(3) . . . . ?
C5 C10 C16 C14 175.8(3) . . . . ?
C6 N2 C9 O2 -174.1(3) . . . . ?
C6 N2 C9 C8 0.3(4) . . . . ?
C6 N2 B1 F2 117.0(4) . . . . ?
C6 N2 B1 F3 -119.4(3) . . . . ?
C6 N2 B1 N1 -0.8(5) . . . . ?
C6 C5 C10 C11 123.8(3) . . . . ?
C6 C5 C10 C16 -52.7(4) . . . . ?
C6 C7 C8 I2 178.1(2) . . . . ?
C6 C7 C8 C9 1.0(4) . . . . ?
C7 C8 C9 O2 172.7(4) . . . . ?
C7 C8 C9 N2 -0.8(4) . . . . ?
C9 O2 C23 C24 49.7(5) . . . . ?
C9 O2 C23 C28 -133.9(4) . . . . ?
C9 N2 C6 C5 177.8(3) . . . . ?
C9 N2 C6 C7 0.4(4) . . . . ?
C9 N2 B1 F2 -55.7(5) . . . . ?
C9 N2 B1 F3 68.0(5) . . . . ?
C9 N2 B1 N1 -173.5(3) . . . . ?
C10 C5 C6 N2 -178.3(3) . . . . ?
C10 C5 C6 C7 -1.4(5) . . . . ?
C10 C11 C12 C13 -1.5(5) . . . . ?
C11 C10 C16 C14 -0.8(5) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
C11 C12 C13 C15 -179.5(4) . . . . ?
C12 C13 C14 C16 0.6(5) . . . . ?
C13 C14 C16 C10 -0.4(5) . . . . ?
C15 C13 C14 C16 -179.6(4) . . . . ?
C16 C10 C11 C12 1.7(5) . . . . ?
C17 O1 C1 N1 -80.2(4) . . . . ?
C17 O1 C1 C2 106.9(4) . . . . ?
C17 C18 C19 C20 -0.6(6) . . . . ?
C18 C17 C22 C21 -2.6(6) . . . . ?
C18 C19 C20 C21 -0.1(7) . . . . ?
C19 C20 C21 C22 -0.6(7) . . . . ?
C20 C21 C22 C17 1.9(7) . . . . ?
C22 C17 C18 C19 2.0(6) . . . . ?
C23 O2 C9 N2 -144.9(3) . . . . ?
C23 O2 C9 C8 41.9(6) . . . . ?
C23 C24 C25 C26 -2.2(7) . . . . ?
C24 C23 C28 C27 -0.9(6) . . . . ?
C24 C25 C26 C27 0.7(7) . . . . ?
C25 C26 C27 C28 0.7(7) . . . . ?
C26 C27 C28 C23 -0.6(7) . . . . ?
C28 C23 C24 C25 2.3(6) . . . . ?
B1 N1 C1 O1 2.6(5) . . . . ?
B1 N1 C1 C2 176.5(3) . . . . ?
B1 N1 C4 C3 -176.0(3) . . . . ?
B1 N1 C4 C5 6.6(5) . . . . ?
B1 N2 C6 C5 4.0(5) . . . . ?
B1 N2 C6 C7 -173.5(3) . . . . ?
B1 N2 C9 O2 -0.3(5) . . . . ?
B1 N2 C9 C8 174.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo211213a
_database_code_depnum_ccdc_archive 'CCDC 2202489'
loop_
_audit_author_name
_audit_author_address
BODIPY-X
;Hangzhou Normal University
China
;
_audit_update_record             
;
2022-08-20 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;
_audit_creation_date             2021-12-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H19 B F2 I2 N2 Se2'
_chemical_formula_sum            'C28 H19 B F2 I2 N2 Se2'
_chemical_formula_weight         843.98
_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'
F F 0.0171 0.0103 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.779(2)
_cell_length_b                   10.9831(18)
_cell_length_c                   18.764(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.115(4)
_cell_angle_gamma                90
_cell_volume                     2894.9(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1619
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.43
_cell_measurement_theta_min      2.354
_shelx_estimated_absorpt_T_max   0.601
_shelx_estimated_absorpt_T_min   0.538
_exptl_absorpt_coefficient_mu    4.720
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0517 before and 0.0370 after correction.
The Ratio of minimum to maximum transmission is 0.8496.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.936
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19245
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         1.541
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3235
_reflns_number_total             5390
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         2.785
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.149
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5390
_refine_ls_number_restraints     116
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0660
_refine_ls_restrained_S_all      1.062
_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)+(0.1156P)²+4.1404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1955
_refine_ls_wR_factor_ref         0.2145
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14-C13 = C11-C10 = C10-C15
 1.37 with sigma of 0.02
 C14-C15
 1.38 with sigma of 0.02
 C13-C12 = C12-C11
 1.36 with sigma of 0.02
 C14-C10
 2.38 with sigma of 0.04
 C13-C11
 2.36 with sigma of 0.04
 C14-C12 = C12-C10 = C11-C15
 2.37 with sigma of 0.04
 C14-C13 \\sim C13-C12 \\sim C12-C11 \\sim C11-C10 \\sim C10-C15 \\sim C15-C14
 with sigma of 0.02
 C14-C10 \\sim C14-C12 \\sim C10-C12 \\sim C11-C13 \\sim C11-C15 \\sim C15-C13
 with sigma of 0.04
3. Restrained planarity
 C10, C11, C12, C13, C14, C15
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C10, C11, C12, C13, C14, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17),
 C21(H21), C20(H20), C19(H19), C18(H18), C23(H23), C24(H24), C26(H26), C27(H27)
6.b Fitted hexagon refined as free rotating group:
 C17(C16,C21,C20,C19,C18), C22(C23,C24,C25,C26,C27)
6.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_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 0.69823(5) 0.95261(7) 0.49199(4) 0.0722(3) Uani 1 1 d . . . . .
I2 I 0.22069(6) 0.71054(10) 0.80708(5) 0.0937(4) Uani 1 1 d . . . . .
Se1 Se 0.68176(9) 1.09461(10) 0.67413(7) 0.0710(4) Uani 1 1 d . . . . .
Se2 Se 0.40992(9) 0.96429(11) 0.85239(7) 0.0756(4) Uani 1 1 d . . . . .
F1 F 0.4955(5) 1.0592(5) 0.7197(4) 0.0743(17) Uani 1 1 d . . . . .
F2 F 0.5939(4) 0.9096(6) 0.7792(3) 0.0715(16) Uani 1 1 d . . . . .
N1 N 0.5419(5) 0.9096(7) 0.6455(4) 0.0513(18) Uani 1 1 d . . . . .
N2 N 0.4299(5) 0.8578(8) 0.7183(4) 0.058(2) Uani 1 1 d . . . . .
C1 C 0.3838(7) 0.8540(11) 0.7702(6) 0.065(3) Uani 1 1 d . . . . .
C2 C 0.3136(7) 0.7619(11) 0.7517(6) 0.065(3) Uani 1 1 d . . . . .
C3 C 0.3175(7) 0.7068(11) 0.6847(6) 0.070(3) Uani 1 1 d . . . . .
H3 H 0.2792 0.6439 0.6586 0.084 Uiso 1 1 calc R U . . .
C4 C 0.3918(7) 0.7671(10) 0.6651(5) 0.059(3) Uani 1 1 d . . . . .
C5 C 0.4249(7) 0.7472(10) 0.6045(6) 0.061(3) Uani 1 1 d . . . . .
C6 C 0.4971(7) 0.8195(9) 0.5937(5) 0.055(2) Uani 1 1 d . . . . .
C7 C 0.5419(7) 0.8202(10) 0.5364(6) 0.064(3) Uani 1 1 d . . . . .
H7 H 0.5273 0.7699 0.4945 0.076 Uiso 1 1 calc R U . . .
C8 C 0.6099(6) 0.9083(9) 0.5545(5) 0.051(2) Uani 1 1 d . . . . .
C9 C 0.6074(7) 0.9621(8) 0.6212(6) 0.055(2) Uani 1 1 d . . . . .
C10 C 0.4661(8) 0.8554(11) 0.9316(6) 0.084(3) Uani 1 1 d D U . . .
C11 C 0.4247(9) 0.8240(13) 0.9847(6) 0.116(5) Uani 1 1 d D U . . .
H11 H 0.3642 0.8532 0.9805 0.139 Uiso 1 1 calc R U . . .
C12 C 0.4697(11) 0.7512(15) 1.0432(7) 0.141(6) Uani 1 1 d D U . . .
H12 H 0.4402 0.7336 1.0792 0.169 Uiso 1 1 calc R U . . .
C13 C 0.5563(12) 0.704(2) 1.0507(10) 0.173(7) Uani 1 1 d D U . . .
H13 H 0.5825 0.6438 1.0863 0.208 Uiso 1 1 calc R U . . .
C14 C 0.6044(12) 0.746(2) 1.0043(11) 0.195(8) Uani 1 1 d D U . . .
H14 H 0.6692 0.7311 1.0150 0.235 Uiso 1 1 calc R U . . .
C15 C 0.5555(11) 0.812(2) 0.9411(9) 0.168(7) Uani 1 1 d D U . . .
H15 H 0.5841 0.8260 0.9043 0.201 Uiso 1 1 calc R U . . .
C17 C 0.8750(6) 1.1025(6) 0.6831(6) 0.105(5) Uani 1 1 d G . . . .
H17 H 0.8609 1.1821 0.6665 0.126 Uiso 1 1 calc R U . . .
C16 C 0.8042(4) 1.0285(6) 0.6942(5) 0.059(3) Uani 1 1 d G . . . .
C21 C 0.8252(7) 0.9095(6) 0.7190(5) 0.088(4) Uani 1 1 d G . . . .
H21 H 0.7779 0.8600 0.7265 0.105 Uiso 1 1 calc R U . . .
C20 C 0.9169(8) 0.8644(7) 0.7327(5) 0.103(5) Uani 1 1 d G . . . .
H20 H 0.9309 0.7847 0.7493 0.124 Uiso 1 1 calc R U . . .
C19 C 0.9876(5) 0.9383(12) 0.7216(6) 0.134(7) Uani 1 1 d G . . . .
H19 H 1.0490 0.9081 0.7307 0.160 Uiso 1 1 calc R U . . .
C18 C 0.9667(5) 1.0574(11) 0.6968(7) 0.145(7) Uani 1 1 d G . . . .
H18 H 1.0140 1.1068 0.6893 0.174 Uiso 1 1 calc R U . . .
C22 C 0.3810(6) 0.6457(7) 0.5504(4) 0.062(3) Uani 1 1 d G . . . .
C23 C 0.3763(7) 0.5266(8) 0.5741(3) 0.111(5) Uani 1 1 d G . . . .
H23 H 0.4023 0.5068 0.6245 0.133 Uiso 1 1 calc R U . . .
C24 C 0.3329(7) 0.4371(6) 0.5223(5) 0.115(5) Uani 1 1 d G . . . .
H24 H 0.3298 0.3574 0.5382 0.138 Uiso 1 1 calc R U . . .
C25 C 0.2941(6) 0.4667(7) 0.4469(4) 0.076(3) Uani 1 1 d G . . . .
C26 C 0.2987(7) 0.5858(8) 0.4232(3) 0.095(4) Uani 1 1 d G . . . .
H26 H 0.2728 0.6056 0.3728 0.114 Uiso 1 1 calc R U . . .
C27 C 0.3422(7) 0.6753(6) 0.4750(4) 0.099(4) Uani 1 1 d G . . . .
H27 H 0.3452 0.7550 0.4591 0.119 Uiso 1 1 calc R U . . .
C28 C 0.2413(11) 0.3712(13) 0.3896(8) 0.105(5) Uani 1 1 d . . . . .
H28A H 0.1798 0.3565 0.3951 0.157 Uiso 1 1 calc R U . . .
H28B H 0.2772 0.2969 0.3980 0.157 Uiso 1 1 calc R U . . .
H28C H 0.2338 0.4005 0.3399 0.157 Uiso 1 1 calc R U . . .
B1 B 0.5172(9) 0.9407(11) 0.7191(7) 0.059(3) 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 C8 2.066(9) . ?
I2 C2 2.043(9) . ?
Se1 C9 1.906(10) . ?
Se1 C16 1.876(6) . ?
Se2 C1 1.903(10) . ?
Se2 C10 1.888(11) . ?
F1 B1 1.340(13) . ?
F2 B1 1.370(14) . ?
N1 C6 1.401(12) . ?
N1 C9 1.322(12) . ?
N1 B1 1.572(13) . ?
N2 C1 1.352(12) . ?
N2 C4 1.399(12) . ?
N2 B1 1.576(14) . ?
C1 C2 1.413(15) . ?
C2 C3 1.411(15) . ?
C3 H3 0.9300 . ?
C3 C4 1.426(14) . ?
C4 C5 1.387(13) . ?
C5 C6 1.395(14) . ?
C5 C22 1.512(11) . ?
C6 C7 1.427(13) . ?
C7 H7 0.9300 . ?
C7 C8 1.360(14) . ?
C8 C9 1.396(13) . ?
C10 C11 1.365(10) . ?
C10 C15 1.364(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.355(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.349(11) . ?
C13 H13 0.9300 . ?
C13 C14 1.367(11) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(11) . ?
C15 H15 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.3900 . ?
C17 C18 1.3900 . ?
C16 C21 1.3900 . ?
C21 H21 0.9300 . ?
C21 C20 1.3900 . ?
C20 H20 0.9300 . ?
C20 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C18 1.3900 . ?
C18 H18 0.9300 . ?
C22 C23 1.3900 . ?
C22 C27 1.3900 . ?
C23 H23 0.9300 . ?
C23 C24 1.3900 . ?
C24 H24 0.9300 . ?
C24 C25 1.3900 . ?
C25 C26 1.3900 . ?
C25 C28 1.531(14) . ?
C26 H26 0.9300 . ?
C26 C27 1.3900 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 Se1 C9 100.0(4) . . ?
C10 Se2 C1 99.4(5) . . ?
C6 N1 B1 125.1(8) . . ?
C9 N1 C6 107.9(8) . . ?
C9 N1 B1 127.0(8) . . ?
C1 N2 C4 108.1(8) . . ?
C1 N2 B1 127.3(8) . . ?
C4 N2 B1 124.4(8) . . ?
N2 C1 Se2 122.9(8) . . ?
N2 C1 C2 109.9(8) . . ?
C2 C1 Se2 127.2(8) . . ?
C1 C2 I2 129.1(8) . . ?
C3 C2 I2 123.7(8) . . ?
C3 C2 C1 107.3(8) . . ?
C2 C3 H3 126.9 . . ?
C2 C3 C4 106.2(9) . . ?
C4 C3 H3 126.9 . . ?
N2 C4 C3 108.5(8) . . ?
C5 C4 N2 122.1(9) . . ?
C5 C4 C3 129.4(10) . . ?
C4 C5 C6 120.7(9) . . ?
C4 C5 C22 118.7(9) . . ?
C6 C5 C22 120.7(8) . . ?
N1 C6 C7 106.8(8) . . ?
C5 C6 N1 121.3(8) . . ?
C5 C6 C7 131.9(9) . . ?
C6 C7 H7 126.4 . . ?
C8 C7 C6 107.1(9) . . ?
C8 C7 H7 126.4 . . ?
C7 C8 I1 125.0(7) . . ?
C7 C8 C9 107.5(8) . . ?
C9 C8 I1 127.4(7) . . ?
N1 C9 Se1 121.3(7) . . ?
N1 C9 C8 110.6(8) . . ?
C8 C9 Se1 128.2(7) . . ?
C11 C10 Se2 123.2(8) . . ?
C15 C10 Se2 119.8(9) . . ?
C15 C10 C11 116.8(10) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.4(11) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.6(11) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 121.1 . . ?
C12 C13 C14 117.7(12) . . ?
C14 C13 H13 121.1 . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.2(12) . . ?
C15 C14 H14 120.4 . . ?
C10 C15 C14 121.5(11) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C16 Se1 117.9(5) . . ?
C21 C16 Se1 122.1(5) . . ?
C21 C16 C17 120.0 . . ?
C16 C21 H21 120.0 . . ?
C16 C21 C20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C23 C22 C5 122.2(7) . . ?
C23 C22 C27 120.0 . . ?
C27 C22 C5 117.8(7) . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 120.0 . . ?
C24 C25 C28 120.9(8) . . ?
C26 C25 C28 119.0(8) . . ?
C25 C26 H26 120.0 . . ?
C25 C26 C27 120.0 . . ?
C27 C26 H26 120.0 . . ?
C22 C27 H27 120.0 . . ?
C26 C27 C22 120.0 . . ?
C26 C27 H27 120.0 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
F1 B1 F2 112.0(9) . . ?
F1 B1 N1 109.9(9) . . ?
F1 B1 N2 111.3(9) . . ?
F2 B1 N1 108.1(9) . . ?
F2 B1 N2 109.2(9) . . ?
N1 B1 N2 106.2(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 C8 C9 Se1 1.5(14) . . . . ?
I1 C8 C9 N1 -179.7(7) . . . . ?
I2 C2 C3 C4 -179.2(8) . . . . ?
Se1 C16 C21 C20 179.6(6) . . . . ?
Se2 C1 C2 I2 -2.7(16) . . . . ?
Se2 C1 C2 C3 177.4(8) . . . . ?
Se2 C10 C11 C12 -176.0(11) . . . . ?
Se2 C10 C15 C14 170.6(19) . . . . ?
N1 C6 C7 C8 -0.3(11) . . . . ?
N2 C1 C2 I2 179.9(8) . . . . ?
N2 C1 C2 C3 0.0(13) . . . . ?
N2 C4 C5 C6 -1.3(16) . . . . ?
N2 C4 C5 C22 178.9(9) . . . . ?
C1 Se2 C10 C11 -112.5(10) . . . . ?
C1 Se2 C10 C15 72.6(15) . . . . ?
C1 N2 C4 C3 1.3(12) . . . . ?
C1 N2 C4 C5 -179.5(10) . . . . ?
C1 N2 B1 F1 -59.9(14) . . . . ?
C1 N2 B1 F2 64.3(13) . . . . ?
C1 N2 B1 N1 -179.4(10) . . . . ?
C1 C2 C3 C4 0.7(13) . . . . ?
C2 C3 C4 N2 -1.2(12) . . . . ?
C2 C3 C4 C5 179.6(11) . . . . ?
C3 C4 C5 C6 177.8(11) . . . . ?
C3 C4 C5 C22 -2.1(17) . . . . ?
C4 N2 C1 Se2 -178.3(8) . . . . ?
C4 N2 C1 C2 -0.8(12) . . . . ?
C4 N2 B1 F1 125.6(10) . . . . ?
C4 N2 B1 F2 -110.3(10) . . . . ?
C4 N2 B1 N1 6.0(14) . . . . ?
C4 C5 C6 N1 3.6(16) . . . . ?
C4 C5 C6 C7 -178.4(11) . . . . ?
C4 C5 C22 C23 -54.3(12) . . . . ?
C4 C5 C22 C27 124.0(9) . . . . ?
C5 C6 C7 C8 -178.5(11) . . . . ?
C5 C22 C23 C24 178.3(8) . . . . ?
C5 C22 C27 C26 -178.3(8) . . . . ?
C6 N1 C9 Se1 177.6(7) . . . . ?
C6 N1 C9 C8 -1.2(11) . . . . ?
C6 N1 B1 F1 -124.3(10) . . . . ?
C6 N1 B1 F2 113.3(10) . . . . ?
C6 N1 B1 N2 -3.7(14) . . . . ?
C6 C5 C22 C23 125.9(10) . . . . ?
C6 C5 C22 C27 -55.8(12) . . . . ?
C6 C7 C8 I1 -179.7(7) . . . . ?
C6 C7 C8 C9 -0.5(11) . . . . ?
C7 C8 C9 Se1 -177.7(8) . . . . ?
C7 C8 C9 N1 1.1(12) . . . . ?
C9 Se1 C16 C17 136.0(5) . . . . ?
C9 Se1 C16 C21 -43.6(6) . . . . ?
C9 N1 C6 C5 179.4(10) . . . . ?
C9 N1 C6 C7 0.9(11) . . . . ?
C9 N1 B1 F1 55.8(14) . . . . ?
C9 N1 B1 F2 -66.7(13) . . . . ?
C9 N1 B1 N2 176.3(9) . . . . ?
C10 C11 C12 C13 -1.9(19) . . . . ?
C11 C10 C15 C14 -5(3) . . . . ?
C11 C12 C13 C14 10(3) . . . . ?
C12 C13 C14 C15 -16(4) . . . . ?
C13 C14 C15 C10 13(4) . . . . ?
C15 C10 C11 C12 -1.0(17) . . . . ?
C17 C16 C21 C20 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C16 C21 C20 C19 0.0 . . . . ?
C21 C20 C19 C18 0.0 . . . . ?
C20 C19 C18 C17 0.0 . . . . ?
C18 C17 C16 Se1 -179.6(6) . . . . ?
C18 C17 C16 C21 0.0 . . . . ?
C22 C5 C6 N1 -176.6(9) . . . . ?
C22 C5 C6 C7 1.4(18) . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C22 C27 C26 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C23 C24 C25 C28 -176.7(10) . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C25 C26 C27 C22 0.0 . . . . ?
C27 C22 C23 C24 0.0 . . . . ?
C28 C25 C26 C27 176.8(10) . . . . ?
B1 N1 C6 C5 -0.6(15) . . . . ?
B1 N1 C6 C7 -179.1(9) . . . . ?
B1 N1 C9 Se1 -2.4(14) . . . . ?
B1 N1 C9 C8 178.7(9) . . . . ?
B1 N2 C1 Se2 6.4(15) . . . . ?
B1 N2 C1 C2 -176.1(10) . . . . ?
B1 N2 C4 C3 176.7(10) . . . . ?
B1 N2 C4 C5 -4.1(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo211115b
_database_code_depnum_ccdc_archive 'CCDC 2202488'
loop_
_audit_author_name
_audit_author_address
BODIPY-X
;Hangzhou Normal University
China
;
_audit_update_record             
;
2022-08-20 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;
_audit_creation_date             2021-11-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H19 B F2 I2 N2 S2'
_chemical_formula_sum            'C29 H19 B0.25 F2 I2 N2 S2'
_chemical_formula_weight         754.08
_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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.6906(9)
_cell_length_b                   11.0622(7)
_cell_length_c                   18.6098(12)
_cell_angle_alpha                90
_cell_angle_beta                 108.0770(10)
_cell_angle_gamma                90
_cell_volume                     2875.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7527
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.223
_cell_measurement_theta_min      2.303
_shelx_estimated_absorpt_T_max   0.764
_shelx_estimated_absorpt_T_min   0.718
_exptl_absorpt_coefficient_mu    2.367
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0719 before and 0.0388 after correction.
The Ratio of minimum to maximum transmission is 0.7760.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1457
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.463
_diffrn_reflns_theta_min         1.552
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5125
_reflns_number_total             8057
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         1.283
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         8057
_refine_ls_number_restraints     374
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0643P)²+3.6041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1424
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C32-C27 = C27-C34 = C34-C33 = C30-C33 = C31-C32 = C31-C30
 1.39 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=Sof(C12)=Sof(H12)=Sof(C11)=Sof(H11)=1-
 FVAR(1)
 Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=FVAR(1)
 Sof(H30A)=Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=1-FVAR(2)
 Sof(H30)=Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C15(H15), C14(H14), C12(H12), C11(H11), C17(H17), C18(H18),
 C19(H19), C20(H20), C24(H24), C23(H23), C22(H22), C26(H26), C25(H25), C28(H28),
  C29(H29), C30(H30), C30(H30A), C31(H31), C32(H32), C33(H33), C34(H34)
5.b Fitted hexagon refined as free rotating group:
 C10(C15,C14,C13,C12,C11), C24(C23,C22,C21,C26,C25)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 0.29443(2) 0.94635(3) 0.50749(2) 0.06239(12) Uani 1 1 d . . . . .
I2 I 0.77975(3) 0.71386(4) 0.19265(2) 0.08623(16) Uani 1 1 d . . . . .
S1 S 0.32109(9) 1.08338(10) 0.33082(8) 0.0600(3) Uani 1 1 d . . . . .
S2 S 0.59107(11) 0.95505(12) 0.15374(7) 0.0688(3) Uani 1 1 d . . . . .
F1 F 0.5071(2) 1.0637(2) 0.28170(19) 0.0701(8) Uani 1 1 d . . . . .
F2 F 0.40843(19) 0.9106(3) 0.22336(15) 0.0647(7) Uani 1 1 d . . . . .
N1 N 0.4621(2) 0.9145(3) 0.35848(18) 0.0423(7) Uani 1 1 d . . . . .
N2 N 0.5734(2) 0.8642(3) 0.28541(19) 0.0513(8) Uani 1 1 d . . . . .
C1 C 0.3913(3) 0.9637(3) 0.3808(2) 0.0447(8) Uani 1 1 d . . . . .
C2 C 0.3896(3) 0.9094(4) 0.4485(2) 0.0454(8) Uani 1 1 d . . . . .
C3 C 0.4605(3) 0.8243(4) 0.4672(2) 0.0498(9) Uani 1 1 d . . . . .
H3 H 0.475562 0.773847 0.509251 0.060 Uiso 1 1 calc R U . . .
C4 C 0.5067(3) 0.8269(4) 0.4110(2) 0.0440(8) Uani 1 1 d . . . . .
C5 C 0.5817(3) 0.7576(4) 0.4015(2) 0.0489(9) Uani 1 1 d . . . . .
C6 C 0.6147(3) 0.7774(4) 0.3399(3) 0.0540(10) Uani 1 1 d . . . . .
C7 C 0.6871(3) 0.7166(4) 0.3193(3) 0.0571(11) Uani 1 1 d . . . . .
H7 H 0.726166 0.654988 0.346148 0.069 Uiso 1 1 calc R U . . .
C8 C 0.6887(3) 0.7660(5) 0.2516(3) 0.0589(11) Uani 1 1 d . . . . .
C9 C 0.6179(3) 0.8579(4) 0.2312(3) 0.0551(10) Uani 1 1 d . . . . .
C10 C 0.6262(3) 0.6638(3) 0.4580(2) 0.0537(10) Uani 1 1 d G . . . .
C15 C 0.5691(2) 0.5713(6) 0.4708(4) 0.116(8) Uani 0.400(6) 1 d G . P A -2
H15 H 0.504021 0.569736 0.444417 0.140 Uiso 0.400(6) 1 calc R U P A -2
C14 C 0.6093(3) 0.4813(5) 0.5231(4) 0.095(6) Uani 0.400(6) 1 d G . P A -2
H14 H 0.571131 0.419389 0.531693 0.114 Uiso 0.400(6) 1 calc R U P A -2
C13 C 0.7067(3) 0.4837(3) 0.5625(2) 0.0597(11) Uani 1 1 d G . . A .
C12 C 0.7638(2) 0.5761(5) 0.5497(3) 0.056(3) Uani 0.400(6) 1 d G . P A -2
H12 H 0.828879 0.577735 0.576070 0.067 Uiso 0.400(6) 1 calc R U P A -2
C11 C 0.7236(3) 0.6662(4) 0.4974(3) 0.053(3) Uani 0.400(6) 1 d G . P A -2
H11 H 0.761771 0.728084 0.488794 0.064 Uiso 0.400(6) 1 calc R U P A -2
C16 C 0.7509(5) 0.3797(5) 0.6163(3) 0.0828(17) Uani 1 1 d . . . . .
H16A H 0.818065 0.394386 0.639325 0.124 Uiso 1 1 calc R U . A .
H16B H 0.742067 0.305227 0.588541 0.124 Uiso 1 1 calc R U . . .
H16C H 0.720226 0.374310 0.654894 0.124 Uiso 1 1 calc R U . . .
C17 C 0.6995(6) 0.5866(7) 0.5811(4) 0.0532(18) Uani 0.600(6) 1 d . . P A -1
H17 H 0.722747 0.606140 0.632182 0.064 Uiso 0.600(6) 1 calc R U P A -1
C18 C 0.6582(5) 0.6777(7) 0.5297(4) 0.0514(17) Uani 0.600(6) 1 d . . P A -1
H18 H 0.653368 0.754155 0.548966 0.062 Uiso 0.600(6) 1 calc R U P A -1
C19 C 0.6290(5) 0.5336(6) 0.4299(4) 0.0510(17) Uani 0.600(6) 1 d . . P A -1
H19 H 0.604043 0.514940 0.378804 0.061 Uiso 0.600(6) 1 calc R U P A -1
C20 C 0.6691(6) 0.4454(7) 0.4820(4) 0.0544(18) Uani 0.600(6) 1 d . . P A -1
H20 H 0.672563 0.365379 0.467712 0.065 Uiso 0.600(6) 1 calc R U P A -1
C24 C 0.0196(2) 0.9353(4) 0.2634(3) 0.130(3) Uani 1 1 d G . . . .
H24 H -0.042944 0.906475 0.249339 0.156 Uiso 1 1 calc R U . . .
C23 C 0.0941(3) 0.8586(3) 0.2625(3) 0.0921(19) Uani 1 1 d G . . . .
H23 H 0.081498 0.778403 0.247809 0.111 Uiso 1 1 calc R U . . .
C22 C 0.1876(2) 0.9018(2) 0.2835(2) 0.0676(12) Uani 1 1 d G . . . .
H22 H 0.237464 0.850425 0.282892 0.081 Uiso 1 1 calc R U . . .
C21 C 0.20647(19) 1.0216(3) 0.3054(2) 0.0504(9) Uani 1 1 d G . . . .
C26 C 0.1319(3) 1.0984(3) 0.3064(3) 0.098(2) Uani 1 1 d G . . . .
H26 H 0.144547 1.178591 0.321037 0.117 Uiso 1 1 calc R U . . .
C25 C 0.0385(2) 1.0552(4) 0.2853(4) 0.156(5) Uani 1 1 d G . . . .
H25 H -0.011419 1.106572 0.285953 0.187 Uiso 1 1 calc R U . . .
C27 C 0.5442(4) 0.8526(6) 0.0771(3) 0.0756(14) Uani 1 1 d D . . . .
C28 C 0.5765(5) 0.8522(8) 0.0173(4) 0.106(2) Uani 1 1 d . . . . .
H28 H 0.627435 0.901890 0.017106 0.127 Uiso 1 1 calc R U . . .
C29 C 0.5352(7) 0.7791(10) -0.0439(4) 0.125(3) Uani 1 1 d . . . . .
H29 H 0.558485 0.779947 -0.085010 0.150 Uiso 1 1 calc R U . . .
C30 C 0.4605(9) 0.7054(13) -0.0448(6) 0.176(5) Uani 1 1 d D . . . .
H30 H 0.409728 0.687230 -0.087699 0.211 Uiso 0.462(16) 1 calc R U P B 1
H30A H 0.447024 0.634611 -0.073112 0.211 Uiso 0.538(16) 1 calc R U P B 2
C31 C 0.4707(14) 0.6611(18) 0.0271(9) 0.122(6) Uani 0.462(16) 1 d D . P B 1
H31 H 0.457782 0.580945 0.035532 0.146 Uiso 0.462(16) 1 calc R U P B 1
C32 C 0.5010(13) 0.7434(14) 0.0849(9) 0.093(5) Uani 0.462(16) 1 d D . P B 1
H32 H 0.492282 0.725453 0.131120 0.111 Uiso 0.462(16) 1 calc R U P B 1
C33 C 0.4045(12) 0.7457(17) 0.0014(8) 0.122(6) Uani 0.538(16) 1 d D . P B 2
H33 H 0.340216 0.724275 -0.011140 0.147 Uiso 0.538(16) 1 calc R U P B 2
C34 C 0.4462(9) 0.8172(15) 0.0654(7) 0.090(4) Uani 0.538(16) 1 d D . P B 2
H34 H 0.412714 0.840390 0.098124 0.108 Uiso 0.538(16) 1 calc R U P B 2
B1 B 0.4855(3) 0.9450(4) 0.2837(3) 0.0482(10) 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 C2 2.069(4) . ?
I2 C8 2.058(4) . ?
S1 C1 1.757(4) . ?
S1 C21 1.741(3) . ?
S2 C9 1.742(5) . ?
S2 C27 1.784(6) . ?
F1 B1 1.354(5) . ?
F2 B1 1.378(6) . ?
N1 C1 1.349(5) . ?
N1 C4 1.388(5) . ?
N1 B1 1.570(6) . ?
N2 C6 1.391(5) . ?
N2 C9 1.363(5) . ?
N2 B1 1.563(6) . ?
C1 C2 1.403(6) . ?
C2 C3 1.367(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.413(5) . ?
C4 C5 1.398(6) . ?
C5 C6 1.395(6) . ?
C5 C10 1.476(5) . ?
C6 C7 1.407(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.380(7) . ?
C8 C9 1.420(7) . ?
C10 C15 1.3900 . ?
C10 C11 1.3900 . ?
C10 C18 1.280(8) . ?
C10 C19 1.537(8) . ?
C15 H15 0.9300 . ?
C15 C14 1.3900 . ?
C14 H14 0.9300 . ?
C14 C13 1.3900 . ?
C13 C12 1.3900 . ?
C13 C16 1.531(6) . ?
C13 C17 1.204(8) . ?
C13 C20 1.488(8) . ?
C12 H12 0.9300 . ?
C12 C11 1.3900 . ?
C11 H11 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C18 1.392(10) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.373(10) . ?
C20 H20 0.9300 . ?
C24 H24 0.9300 . ?
C24 C23 1.3900 . ?
C24 C25 1.3900 . ?
C23 H23 0.9300 . ?
C23 C22 1.3900 . ?
C22 H22 0.9300 . ?
C22 C21 1.3900 . ?
C21 C26 1.3900 . ?
C26 H26 0.9300 . ?
C26 C25 1.3900 . ?
C25 H25 0.9300 . ?
C27 C28 1.339(8) . ?
C27 C32 1.393(13) . ?
C27 C34 1.442(11) . ?
C28 H28 0.9300 . ?
C28 C29 1.374(11) . ?
C29 H29 0.9300 . ?
C29 C30 1.363(13) . ?
C30 H30 0.9300 . ?
C30 H30A 0.9300 . ?
C30 C31 1.388(15) . ?
C30 C33 1.433(14) . ?
C31 H31 0.9300 . ?
C31 C32 1.374(15) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C33 C34 1.403(14) . ?
C34 H34 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 S1 C1 101.96(17) . . ?
C9 S2 C27 101.6(2) . . ?
C1 N1 C4 107.8(3) . . ?
C1 N1 B1 126.0(3) . . ?
C4 N1 B1 126.1(3) . . ?
C6 N2 B1 125.5(3) . . ?
C9 N2 C6 107.7(3) . . ?
C9 N2 B1 126.6(3) . . ?
N1 C1 S1 121.5(3) . . ?
N1 C1 C2 109.5(3) . . ?
C2 C1 S1 128.8(3) . . ?
C1 C2 I1 126.5(3) . . ?
C3 C2 I1 126.0(3) . . ?
C3 C2 C1 107.4(3) . . ?
C2 C3 H3 126.3 . . ?
C2 C3 C4 107.5(4) . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C3 107.8(3) . . ?
N1 C4 C5 120.9(3) . . ?
C5 C4 C3 131.3(4) . . ?
C4 C5 C10 119.3(4) . . ?
C6 C5 C4 120.4(4) . . ?
C6 C5 C10 120.3(4) . . ?
N2 C6 C5 121.5(4) . . ?
N2 C6 C7 109.1(4) . . ?
C5 C6 C7 129.3(4) . . ?
C6 C7 H7 126.6 . . ?
C8 C7 C6 106.7(4) . . ?
C8 C7 H7 126.6 . . ?
C7 C8 I2 125.0(4) . . ?
C7 C8 C9 108.0(4) . . ?
C9 C8 I2 127.0(3) . . ?
N2 C9 S2 123.0(3) . . ?
N2 C9 C8 108.5(4) . . ?
C8 C9 S2 128.4(3) . . ?
C5 C10 C19 118.0(4) . . ?
C15 C10 C5 118.8(3) . . ?
C15 C10 C11 120.0 . . ?
C11 C10 C5 121.2(3) . . ?
C18 C10 C5 126.6(5) . . ?
C18 C10 C19 115.3(5) . . ?
C10 C15 H15 120.0 . . ?
C10 C15 C14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C13 C16 119.3(4) . . ?
C12 C13 C14 120.0 . . ?
C12 C13 C16 120.6(4) . . ?
C17 C13 C16 125.4(5) . . ?
C17 C13 C20 121.4(5) . . ?
C20 C13 C16 113.2(5) . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17 118.5 . . ?
C13 C17 C18 123.0(6) . . ?
C18 C17 H17 118.5 . . ?
C10 C18 C17 124.8(6) . . ?
C10 C18 H18 117.6 . . ?
C17 C18 H18 117.6 . . ?
C10 C19 H19 120.8 . . ?
C20 C19 C10 118.5(6) . . ?
C20 C19 H19 120.8 . . ?
C13 C20 H20 121.5 . . ?
C19 C20 C13 116.9(6) . . ?
C19 C20 H20 121.5 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 C24 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C22 H22 120.0 . . ?
C23 C22 C21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C21 S1 122.82(19) . . ?
C26 C21 S1 117.17(19) . . ?
C26 C21 C22 120.0 . . ?
C21 C26 H26 120.0 . . ?
C25 C26 C21 120.0 . . ?
C25 C26 H26 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0 . . ?
C26 C25 H25 120.0 . . ?
C28 C27 S2 121.2(5) . . ?
C28 C27 C32 111.9(9) . . ?
C28 C27 C34 117.9(7) . . ?
C32 C27 S2 122.9(7) . . ?
C34 C27 S2 114.4(7) . . ?
C27 C28 H28 119.6 . . ?
C27 C28 C29 120.8(8) . . ?
C29 C28 H28 119.6 . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.6(8) . . ?
C30 C29 H29 119.7 . . ?
C29 C30 H30 124.6 . . ?
C29 C30 H30A 122.7 . . ?
C29 C30 C31 110.7(12) . . ?
C29 C30 C33 114.6(11) . . ?
C31 C30 H30 124.6 . . ?
C33 C30 H30A 122.7 . . ?
C30 C31 H31 122.2 . . ?
C32 C31 C30 115.6(16) . . ?
C32 C31 H31 122.2 . . ?
C27 C32 H32 118.6 . . ?
C31 C32 C27 122.8(14) . . ?
C31 C32 H32 118.6 . . ?
C30 C33 H33 119.9 . . ?
C34 C33 C30 120.2(12) . . ?
C34 C33 H33 119.9 . . ?
C27 C34 H34 122.1 . . ?
C33 C34 C27 115.8(11) . . ?
C33 C34 H34 122.1 . . ?
F1 B1 F2 112.7(4) . . ?
F1 B1 N1 110.5(4) . . ?
F1 B1 N2 110.8(4) . . ?
F2 B1 N1 108.2(3) . . ?
F2 B1 N2 108.9(4) . . ?
N2 B1 N1 105.4(3) . . ?

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 C2 C3 C4 178.5(3) . . . . ?
I2 C8 C9 S2 -2.7(7) . . . . ?
I2 C8 C9 N2 -179.9(3) . . . . ?
S1 C1 C2 I1 5.0(6) . . . . ?
S1 C1 C2 C3 -177.0(3) . . . . ?
S1 C21 C26 C25 178.8(3) . . . . ?
S2 C27 C28 C29 -175.3(7) . . . . ?
S2 C27 C32 C31 -175.5(14) . . . . ?
S2 C27 C34 C33 174.4(11) . . . . ?
N1 C1 C2 I1 -178.7(3) . . . . ?
N1 C1 C2 C3 -0.7(5) . . . . ?
N1 C4 C5 C6 1.6(7) . . . . ?
N1 C4 C5 C10 -179.0(4) . . . . ?
N2 C6 C7 C8 -0.6(6) . . . . ?
C1 S1 C21 C22 -38.3(3) . . . . ?
C1 S1 C21 C26 142.9(3) . . . . ?
C1 N1 C4 C3 -0.3(5) . . . . ?
C1 N1 C4 C5 178.1(4) . . . . ?
C1 N1 B1 F1 60.0(5) . . . . ?
C1 N1 B1 F2 -63.8(5) . . . . ?
C1 N1 B1 N2 179.8(4) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C2 C3 C4 N1 -0.2(5) . . . . ?
C2 C3 C4 C5 -178.3(4) . . . . ?
C3 C4 C5 C6 179.5(5) . . . . ?
C3 C4 C5 C10 -1.1(7) . . . . ?
C4 N1 C1 S1 177.2(3) . . . . ?
C4 N1 C1 C2 0.6(5) . . . . ?
C4 N1 B1 F1 -124.3(4) . . . . ?
C4 N1 B1 F2 111.9(4) . . . . ?
C4 N1 B1 N2 -4.5(6) . . . . ?
C4 C5 C6 N2 -1.3(7) . . . . ?
C4 C5 C6 C7 -178.5(5) . . . . ?
C4 C5 C10 C15 59.0(6) . . . . ?
C4 C5 C10 C11 -121.6(5) . . . . ?
C4 C5 C10 C18 -51.0(7) . . . . ?
C4 C5 C10 C19 124.2(5) . . . . ?
C5 C6 C7 C8 176.8(5) . . . . ?
C5 C10 C15 C14 179.4(4) . . . . ?
C5 C10 C11 C12 -179.4(4) . . . . ?
C5 C10 C18 C17 179.8(6) . . . . ?
C5 C10 C19 C20 -179.1(6) . . . . ?
C6 N2 C9 S2 -177.6(4) . . . . ?
C6 N2 C9 C8 -0.2(5) . . . . ?
C6 N2 B1 F1 124.4(5) . . . . ?
C6 N2 B1 F2 -111.1(5) . . . . ?
C6 N2 B1 N1 4.8(6) . . . . ?
C6 C5 C10 C15 -121.7(5) . . . . ?
C6 C5 C10 C11 57.8(6) . . . . ?
C6 C5 C10 C18 128.4(6) . . . . ?
C6 C5 C10 C19 -56.5(6) . . . . ?
C6 C7 C8 I2 -179.8(4) . . . . ?
C6 C7 C8 C9 0.5(6) . . . . ?
C7 C8 C9 S2 177.0(4) . . . . ?
C7 C8 C9 N2 -0.2(6) . . . . ?
C9 S2 C27 C28 -129.6(6) . . . . ?
C9 S2 C27 C32 26.3(11) . . . . ?
C9 S2 C27 C34 79.2(8) . . . . ?
C9 N2 C6 C5 -177.1(5) . . . . ?
C9 N2 C6 C7 0.5(5) . . . . ?
C9 N2 B1 F1 -61.9(6) . . . . ?
C9 N2 B1 F2 62.6(6) . . . . ?
C9 N2 B1 N1 178.5(4) . . . . ?
C10 C5 C6 N2 179.3(4) . . . . ?
C10 C5 C6 C7 2.1(8) . . . . ?
C10 C15 C14 C13 0.0 . . . . ?
C10 C19 C20 C13 0.3(10) . . . . ?
C15 C10 C11 C12 0.0 . . . . ?
C15 C14 C13 C12 0.0 . . . . ?
C15 C14 C13 C16 -176.3(4) . . . . ?
C14 C13 C12 C11 0.0 . . . . ?
C13 C12 C11 C10 0.0 . . . . ?
C13 C17 C18 C10 -2.3(13) . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
C16 C13 C12 C11 176.3(4) . . . . ?
C16 C13 C17 C18 -179.7(7) . . . . ?
C16 C13 C20 C19 -179.4(7) . . . . ?
C17 C13 C20 C19 2.2(10) . . . . ?
C18 C10 C19 C20 -3.4(9) . . . . ?
C19 C10 C18 C17 4.5(10) . . . . ?
C20 C13 C17 C18 -1.4(11) . . . . ?
C24 C23 C22 C21 0.0 . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C23 C22 C21 S1 -178.7(3) . . . . ?
C23 C22 C21 C26 0.0 . . . . ?
C22 C21 C26 C25 0.0 . . . . ?
C21 S1 C1 N1 120.5(3) . . . . ?
C21 S1 C1 C2 -63.6(4) . . . . ?
C21 C26 C25 C24 0.0 . . . . ?
C25 C24 C23 C22 0.0 . . . . ?
C27 S2 C9 N2 -115.9(4) . . . . ?
C27 S2 C9 C8 67.2(5) . . . . ?
C27 C28 C29 C30 -0.1(15) . . . . ?
C28 C27 C32 C31 -18(2) . . . . ?
C28 C27 C34 C33 22.1(17) . . . . ?
C28 C29 C30 C31 -35.2(19) . . . . ?
C28 C29 C30 C33 26.0(18) . . . . ?
C29 C30 C31 C32 42(2) . . . . ?
C29 C30 C33 C34 -28(2) . . . . ?
C30 C31 C32 C27 -17(3) . . . . ?
C30 C33 C34 C27 4(2) . . . . ?
C32 C27 C28 C29 26.4(14) . . . . ?
C34 C27 C28 C29 -25.0(14) . . . . ?
B1 N1 C1 S1 -6.5(6) . . . . ?
B1 N1 C1 C2 176.9(4) . . . . ?
B1 N1 C4 C3 -176.6(4) . . . . ?
B1 N1 C4 C5 1.8(6) . . . . ?
B1 N2 C6 C5 -2.4(7) . . . . ?
B1 N2 C6 C7 175.3(4) . . . . ?
B1 N2 C9 S2 7.7(7) . . . . ?
B1 N2 C9 C8 -174.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
