# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ot2405a_phboaph-dimer_auto
_database_code_depnum_ccdc_archive 'CCDC 2322217'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2024-05-06 downloaded from the CCDC.
;
_audit_creation_date             2024-05-01
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 B4 F8 N6 O2'
_chemical_formula_sum            'C24 H16 B4 F8 N6 O2'
_chemical_formula_weight         615.67
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           142
_space_group_name_H-M_alt        'I 41/a c d'
_space_group_name_Hall           '-I 4bd 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+1/4, x+3/4, z+1/4'
'y+1/4, -x+1/4, z+3/4'
'-x+1/2, y, -z'
'x, -y, -z+1/2'
'y+1/4, x+3/4, -z+3/4'
'-y+1/4, -x+1/4, -z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+3/4, x+5/4, z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-x+1, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1'
'y+3/4, x+5/4, -z+5/4'
'-y+3/4, -x+3/4, -z+3/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-1/4, -x-3/4, -z-1/4'
'-y-1/4, x-1/4, -z-3/4'
'x-1/2, -y, z'
'-x, y, z-1/2'
'-y-1/4, -x-3/4, z-3/4'
'y-1/4, x-1/4, z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y+1/4, -x-1/4, -z+1/4'
'-y+1/4, x+1/4, -z-1/4'
'x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'-y+1/4, -x-1/4, z-1/4'
'y+1/4, x+1/4, z+1/4'

_cell_length_a                   18.9140(2)
_cell_length_b                   18.9140(2)
_cell_length_c                   27.7587(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9930.4(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9745
_cell_measurement_temperature    100.02(10)
_cell_measurement_theta_max      75.6680
_cell_measurement_theta_min      3.1860
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.702
_exptl_absorpt_coefficient_mu    1.283
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             4960
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.057
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            16042
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.976
_diffrn_reflns_theta_min         4.591
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00 -33.00   0.50    0.64    -- -104.00  61.00-150.00   52
  2  ω   -113.00 -32.00   0.50    0.64    -- -104.00 128.00 -65.00  162
  3  ω    -65.00 -31.00   0.50    0.64    -- -104.00  77.00 -30.00   68
  4  ω     47.00 120.00   0.50    0.16    --   44.51 178.00-120.00  146
  5  ω     70.00 162.00   0.50    0.64    --  108.18  11.00  94.00  184
  6  ω     -7.00 124.00   0.50    0.16    --   44.51  11.00  94.00  262
  7  ω     40.00  73.00   0.50    0.64    --  108.18 -61.00  90.00   66
  8  ω     40.00  65.00   0.50    0.64    --  108.18 -61.00-120.00   50
  9  ω     81.00 111.00   0.50    0.64    --  108.18-125.00-180.00   60
 10  ω     43.00  71.00   0.50    0.64    --  108.18-125.00-180.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0785835000
_diffrn_orient_matrix_UB_12      0.0179891000
_diffrn_orient_matrix_UB_13      0.0080566000
_diffrn_orient_matrix_UB_21      0.0184419000
_diffrn_orient_matrix_UB_22      0.0793342000
_diffrn_orient_matrix_UB_23      0.0011768000
_diffrn_orient_matrix_UB_31      -0.0110993000
_diffrn_orient_matrix_UB_32      0.0044064000
_diffrn_orient_matrix_UB_33      -0.0548668000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2359
_reflns_number_total             2542
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.081
_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)+(0.0720P)²+11.6293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1270
_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), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
;
_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
F1 F 0.34286(5) 0.41746(5) 0.23506(3) 0.0275(3) Uani 1 1 d . . . . .
F2 F 0.24747(5) 0.35022(6) 0.21658(3) 0.0297(3) Uani 1 1 d . . . . .
F3 F 0.34032(7) 0.32898(6) 0.41229(4) 0.0400(3) Uani 1 1 d . . . . .
F4 F 0.24961(7) 0.25480(6) 0.39760(4) 0.0426(3) Uani 1 1 d . . . . .
O1 O 0.34968(7) 0.24973(7) 0.34617(4) 0.0303(3) Uani 1 1 d . . . . .
N1 N 0.23752(7) 0.42823(8) 0.28645(5) 0.0241(3) Uani 1 1 d . . . . .
N2 N 0.30751(8) 0.32588(8) 0.29328(5) 0.0258(3) Uani 1 1 d . . . . .
N3 N 0.27493(8) 0.34381(8) 0.33704(5) 0.0285(3) Uani 1 1 d . . . . .
C1 C 0.19803(9) 0.48686(9) 0.27536(5) 0.0255(4) Uani 1 1 d . . . . .
C2 C 0.15553(9) 0.51700(11) 0.30927(6) 0.0314(4) Uani 1 1 d . . . . .
H2 H 0.127735 0.557188 0.301360 0.038 Uiso 1 1 calc R U . . .
C3 C 0.15291(9) 0.48825(11) 0.35632(6) 0.0317(4) Uani 1 1 d . . . . .
H3 H 0.123053 0.509173 0.379857 0.038 Uiso 1 1 calc R U . . .
C4 C 0.19269(10) 0.43106(10) 0.36811(6) 0.0292(4) Uani 1 1 d . . . . .
H4 H 0.191884 0.411896 0.399742 0.035 Uiso 1 1 calc R U . . .
C5 C 0.23514(9) 0.40119(9) 0.33179(6) 0.0261(4) Uani 1 1 d . . . . .
C6 C 0.34812(9) 0.27117(9) 0.30115(6) 0.0263(4) Uani 1 1 d . . . . .
C7 C 0.38867(9) 0.23221(9) 0.26520(6) 0.0276(4) Uani 1 1 d . . . . .
C8 C 0.37548(10) 0.23960(10) 0.21601(6) 0.0315(4) Uani 1 1 d . . . . .
H8 H 0.341371 0.272655 0.204886 0.038 Uiso 1 1 calc R U . . .
C9 C 0.41288(11) 0.19798(10) 0.18338(7) 0.0361(4) Uani 1 1 d . . . . .
H9 H 0.404411 0.202718 0.149799 0.043 Uiso 1 1 calc R U . . .
C10 C 0.46236(11) 0.14974(10) 0.19979(7) 0.0371(4) Uani 1 1 d . . . . .
H10 H 0.487058 0.120933 0.177371 0.045 Uiso 1 1 calc R U . . .
C11 C 0.47618(11) 0.14307(11) 0.24846(7) 0.0370(4) Uani 1 1 d . . . . .
H11 H 0.510865 0.110452 0.259350 0.044 Uiso 1 1 calc R U . . .
C12 C 0.43934(10) 0.18404(10) 0.28131(7) 0.0322(4) Uani 1 1 d . . . . .
H12 H 0.448545 0.179362 0.314805 0.039 Uiso 1 1 calc R U . . .
B1 B 0.28603(10) 0.38136(10) 0.25265(6) 0.0245(4) Uani 1 1 d . . . . .
B2 B 0.30245(12) 0.29470(11) 0.37752(7) 0.0313(4) 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
F1 B1 1.364(2) . ?
F2 B1 1.372(2) . ?
F3 B2 1.366(2) . ?
F4 B2 1.371(2) . ?
O1 C6 1.3142(19) . ?
O1 B2 1.510(2) . ?
N1 C1 1.372(2) . ?
N1 C5 1.359(2) . ?
N1 B1 1.584(2) . ?
N2 N3 1.4036(19) . ?
N2 C6 1.307(2) . ?
N2 B1 1.593(2) . ?
N3 C5 1.329(2) . ?
N3 B2 1.548(2) . ?
C1 C1 1.493(3) 6_565 ?
C1 C2 1.363(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.415(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.358(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.407(2) . ?
C6 C7 1.458(2) . ?
C7 C8 1.395(2) . ?
C7 C12 1.396(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 B2 111.17(14) . . ?
C1 N1 B1 129.42(13) . . ?
C5 N1 C1 119.59(14) . . ?
C5 N1 B1 110.91(14) . . ?
N3 N2 B1 109.97(13) . . ?
C6 N2 N3 107.75(13) . . ?
C6 N2 B1 142.13(14) . . ?
N2 N3 B2 109.61(14) . . ?
C5 N3 N2 110.55(13) . . ?
C5 N3 B2 139.48(14) . . ?
N1 C1 C1 118.72(15) . 6_565 ?
C2 C1 N1 120.28(15) . . ?
C2 C1 C1 120.80(16) . 6_565 ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.82(17) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.61(16) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.60(15) . . ?
C5 C4 H4 121.2 . . ?
N1 C5 C4 122.08(16) . . ?
N3 C5 N1 112.97(14) . . ?
N3 C5 C4 124.92(15) . . ?
O1 C6 C7 118.88(16) . . ?
N2 C6 O1 114.60(15) . . ?
N2 C6 C7 126.50(15) . . ?
C8 C7 C6 121.67(17) . . ?
C8 C7 C12 120.12(17) . . ?
C12 C7 C6 118.14(16) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.28(18) . . ?
C9 C8 H8 120.4 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.12(18) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.66(18) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.84(19) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 119.97(17) . . ?
C11 C12 H12 120.0 . . ?
F1 B1 F2 111.88(13) . . ?
F1 B1 N1 112.86(14) . . ?
F1 B1 N2 112.47(14) . . ?
F2 B1 N1 111.40(14) . . ?
F2 B1 N2 111.70(14) . . ?
N1 B1 N2 95.57(12) . . ?
F3 B2 F4 110.88(15) . . ?
F3 B2 O1 111.38(17) . . ?
F3 B2 N3 113.86(15) . . ?
F4 B2 O1 110.83(15) . . ?
F4 B2 N3 112.36(17) . . ?
O1 B2 N3 96.81(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.323
_oxdiff_exptl_absorpt_empirical_full_min 0.704
####################################################################### 
# 
# 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_ot2302d_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2322218'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-05-06 downloaded from the CCDC.
;
_audit_creation_date             2023-02-20
_audit_creation_method           
;
Olex2 1.5-ac5-020
(compiled 2021.11.16 svn.r5db059d7 for Rigaku Oxford Diffraction, GUI svn.r6430)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 B4 F6 N6 O3'
_chemical_formula_sum            'C24 H16 B4 F6 N6 O3'
_chemical_formula_weight         593.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     100
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'
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                   8.4265(4)
_cell_length_b                   10.5693(4)
_cell_length_c                   13.8392(6)
_cell_angle_alpha                89.215(3)
_cell_angle_beta                 85.014(4)
_cell_angle_gamma                79.567(3)
_cell_volume                     1207.58(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5615
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.5700
_cell_measurement_theta_min      2.4550
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.41a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.011
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7777
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.451
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00 -15.50   0.50    5.00    --  -24.17 128.00  81.00  169
  2  ω     21.00 101.00   0.50    5.00    --   24.64-128.00   7.00  160
  3  ω    -54.00  26.00   0.50    5.00    --  -24.17 -57.00-180.00  160
  4  ω     21.00  58.00   0.50    5.00    --  -24.17  19.00-120.00   74
  5  ω     21.00  58.00   0.50    5.00    --  -24.17  19.00  90.00   74
  6  ω     21.00  58.00   0.50    5.00    --  -24.17  19.00   0.00   74
  7  ω     21.00  58.00   0.50    5.00    --  -24.17  19.00  30.00   74
  8  ω     21.00  58.00   0.50    5.00    --  -24.17  19.00 120.00   74
  9  ω     21.00  58.00   0.50    5.00    --  -24.17  19.00-150.00   74
 10  ω     21.00  58.00   0.50    5.00    --  -24.17  19.00 150.00   74
 11  ω     21.00  58.00   0.50    5.00    --  -24.17  19.00-180.00   74
 12  ω    -28.00  20.50   0.50    5.00    --   24.64  77.00 120.00   97
 13  ω    -26.00  59.00   0.50    5.00    --   24.64  57.00-120.00  170
 14  ω      2.00  86.00   0.50    5.00    --   24.64 -99.00   0.00  168
 15  ω    -76.00 -17.00   0.50    5.00    --   24.64 -19.00 -90.00  118
 16  ω    -76.00 -17.00   0.50    5.00    --   24.64 -19.00-120.00  118
 17  ω    -28.00  20.50   0.50    5.00    --   24.64  77.00  60.00   97
 18  ω    -76.00 -17.00   0.50    5.00    --   24.64 -19.00 -60.00  118
 19  ω     21.00  46.00   0.50    5.00    --  -24.17  19.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0530830000
_diffrn_orient_matrix_UB_12      0.0034791000
_diffrn_orient_matrix_UB_13      0.0365512000
_diffrn_orient_matrix_UB_21      -0.0624176000
_diffrn_orient_matrix_UB_22      -0.0080636000
_diffrn_orient_matrix_UB_23      0.0361173000
_diffrn_orient_matrix_UB_31      0.0258107000
_diffrn_orient_matrix_UB_32      -0.0676702000
_diffrn_orient_matrix_UB_33      -0.0025323000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6022
_reflns_number_total             7777
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.41a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         7777
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.039
_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)+(0.0633P)²+0.3239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1183
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7444(8)
 0.2556(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_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
F1 F 0.59300(17) 1.29316(12) 0.62086(10) 0.0218(3) Uani 1 1 d . . . . .
O1 O 0.4296(2) 1.16659(14) 0.71334(11) 0.0192(4) Uani 1 1 d . . . . .
N1 N 0.6159(2) 0.99006(17) 0.70334(13) 0.0161(4) Uani 1 1 d . . . . .
C1 C 0.4889(3) 1.0568(2) 0.75408(16) 0.0156(5) Uani 1 1 d . . . . .
F2 F 0.42595(18) 1.19298(13) 0.54276(10) 0.0240(3) Uani 1 1 d . . . . .
O2 O 0.6658(2) 0.75176(14) 0.72011(13) 0.0269(4) Uani 1 1 d . . . . .
N2 N 0.6454(3) 1.05828(17) 0.61787(13) 0.0173(4) Uani 1 1 d . . . . .
C2 C 0.7499(3) 0.9839(2) 0.55439(16) 0.0160(5) Uani 1 1 d . . . . .
F3 F 0.86073(18) 0.86717(13) 0.76323(9) 0.0257(3) Uani 1 1 d . . . . .
O3 O 0.6627(2) 0.35750(14) 0.84477(11) 0.0196(4) Uani 1 1 d . . . . .
N3 N 0.8130(2) 0.86860(16) 0.59280(13) 0.0146(4) Uani 1 1 d . . . . .
C3 C 0.7931(3) 1.0182(2) 0.45858(17) 0.0177(5) Uani 1 1 d . . . . .
H3 H 0.745745 1.098267 0.432298 0.021 Uiso 1 1 calc R U . . .
F4 F 0.62572(18) 0.61658(14) 0.59615(10) 0.0259(3) Uani 1 1 d . . . . .
N4 N 0.9016(2) 0.59584(17) 0.64371(13) 0.0152(4) Uani 1 1 d . . . . .
C4 C 0.9055(3) 0.9323(2) 0.40455(16) 0.0186(5) Uani 1 1 d . . . . .
H4 H 0.937887 0.952524 0.339555 0.022 Uiso 1 1 calc R U . . .
F5 F 0.93251(18) 0.31234(13) 0.88907(10) 0.0264(3) Uani 1 1 d . . . . .
N5 N 0.8555(2) 0.43419(17) 0.74393(14) 0.0176(4) Uani 1 1 d . . . . .
C5 C 0.9738(3) 0.8137(2) 0.44484(16) 0.0169(5) Uani 1 1 d . . . . .
H5 H 1.053623 0.755124 0.407302 0.020 Uiso 1 1 calc R U . . .
F6 F 0.86851(18) 0.20160(12) 0.76497(10) 0.0249(3) Uani 1 1 d . . . . .
N6 N 0.7045(2) 0.51597(17) 0.74639(13) 0.0159(4) Uani 1 1 d . . . . .
C6 C 0.9256(3) 0.7825(2) 0.53775(16) 0.0163(5) Uani 1 1 d . . . . .
C7 C 0.9973(3) 0.6586(2) 0.58156(15) 0.0157(5) Uani 1 1 d . . . . .
C8 C 1.1579(3) 0.6071(2) 0.56076(16) 0.0181(5) Uani 1 1 d . . . . .
H8 H 1.224201 0.650119 0.517553 0.022 Uiso 1 1 calc R U . . .
C9 C 1.2243(3) 0.4896(2) 0.60403(16) 0.0180(5) Uani 1 1 d . . . . .
H9 H 1.335243 0.453249 0.589083 0.022 Uiso 1 1 calc R U . . .
C10 C 1.1304(3) 0.4279(2) 0.66709(16) 0.0170(5) Uani 1 1 d . . . . .
H10 H 1.174679 0.349888 0.697467 0.020 Uiso 1 1 calc R U . . .
C11 C 0.9664(3) 0.4834(2) 0.68562(15) 0.0154(5) Uani 1 1 d . . . . .
C12 C 0.6006(3) 0.4666(2) 0.80421(16) 0.0174(5) Uani 1 1 d . . . . .
C13 C 0.4089(3) 1.0196(2) 0.84469(16) 0.0175(5) Uani 1 1 d . . . . .
C14 C 0.4647(3) 0.9066(2) 0.89423(16) 0.0203(5) Uani 1 1 d . . . . .
H14 H 0.560776 0.850832 0.869813 0.024 Uiso 1 1 calc R U . . .
B014 B 0.7413(3) 0.8572(2) 0.70319(19) 0.0179(5) Uani 1 1 d . . . . .
C15 C 0.3805(3) 0.8758(2) 0.97851(17) 0.0222(5) Uani 1 1 d . . . . .
H15 H 0.417859 0.797772 1.011058 0.027 Uiso 1 1 calc R U . . .
B015 B 0.8396(4) 0.3175(2) 0.81246(19) 0.0193(6) Uani 1 1 d . . . . .
C16 C 0.2416(3) 0.9575(2) 1.01643(17) 0.0228(5) Uani 1 1 d . . . . .
H16 H 0.185307 0.936058 1.075094 0.027 Uiso 1 1 calc R U . . .
B016 B 0.7107(4) 0.6334(2) 0.67342(18) 0.0179(6) Uani 1 1 d . . . . .
C17 C 0.1853(3) 1.0708(2) 0.96822(18) 0.0228(5) Uani 1 1 d . . . . .
H17 H 0.090513 1.126973 0.993955 0.027 Uiso 1 1 calc R U . . .
B017 B 0.5224(3) 1.1853(2) 0.61780(19) 0.0175(5) Uani 1 1 d . . . . .
C18 C 0.2674(3) 1.1016(2) 0.88274(17) 0.0213(5) Uani 1 1 d . . . . .
H18 H 0.227948 1.178610 0.849524 0.026 Uiso 1 1 calc R U . . .
C19 C 0.4299(3) 0.5213(2) 0.82718(16) 0.0176(5) Uani 1 1 d . . . . .
C20 C 0.3575(3) 0.6396(2) 0.79138(17) 0.0218(5) Uani 1 1 d . . . . .
H20 H 0.419525 0.688021 0.749818 0.026 Uiso 1 1 calc R U . . .
C21 C 0.1946(3) 0.6866(2) 0.81656(18) 0.0237(5) Uani 1 1 d . . . . .
H21 H 0.145917 0.767835 0.792665 0.028 Uiso 1 1 calc R U . . .
C22 C 0.1031(3) 0.6168(2) 0.87576(18) 0.0255(6) Uani 1 1 d . . . . .
H22 H -0.008463 0.649503 0.892303 0.031 Uiso 1 1 calc R U . . .
C23 C 0.1737(3) 0.4988(3) 0.91119(19) 0.0291(6) Uani 1 1 d . . . . .
H23 H 0.110445 0.450777 0.952267 0.035 Uiso 1 1 calc R U . . .
C24 C 0.3355(3) 0.4507(2) 0.88713(18) 0.0245(6) Uani 1 1 d . . . . .
H24 H 0.383021 0.369342 0.911332 0.029 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B017 1.381(3) . ?
O1 C1 1.317(3) . ?
O1 B017 1.506(3) . ?
N1 C1 1.321(3) . ?
N1 N2 1.404(3) . ?
N1 B014 1.597(3) . ?
C1 C13 1.455(3) . ?
F2 B017 1.366(3) . ?
O2 B014 1.387(3) . ?
O2 B016 1.390(3) . ?
N2 C2 1.342(3) . ?
N2 B017 1.540(3) . ?
C2 N3 1.359(3) . ?
C2 C3 1.404(3) . ?
F3 B014 1.379(3) . ?
O3 C12 1.316(3) . ?
O3 B015 1.504(3) . ?
N3 C6 1.374(3) . ?
N3 B014 1.605(3) . ?
C3 C4 1.366(3) . ?
F4 B016 1.368(3) . ?
N4 C7 1.374(3) . ?
N4 C11 1.359(3) . ?
N4 B016 1.604(3) . ?
C4 C5 1.410(3) . ?
F5 B015 1.366(3) . ?
N5 N6 1.401(3) . ?
N5 C11 1.353(3) . ?
N5 B015 1.564(3) . ?
C5 C6 1.368(3) . ?
F6 B015 1.370(3) . ?
N6 C12 1.308(3) . ?
N6 B016 1.595(3) . ?
C6 C7 1.484(3) . ?
C7 C8 1.372(3) . ?
C8 C9 1.415(3) . ?
C9 C10 1.365(3) . ?
C10 C11 1.403(3) . ?
C12 C19 1.459(3) . ?
C13 C14 1.396(3) . ?
C13 C18 1.407(3) . ?
C14 C15 1.378(3) . ?
C15 C16 1.390(3) . ?
C16 C17 1.389(3) . ?
C17 C18 1.383(3) . ?
C19 C20 1.393(3) . ?
C19 C24 1.400(3) . ?
C20 C21 1.388(4) . ?
C21 C22 1.375(4) . ?
C22 C23 1.384(4) . ?
C23 C24 1.379(4) . ?

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 B017 111.50(17) . . ?
C1 N1 N2 108.07(17) . . ?
C1 N1 B014 142.07(19) . . ?
N2 N1 B014 109.78(17) . . ?
O1 C1 N1 113.6(2) . . ?
O1 C1 C13 119.0(2) . . ?
N1 C1 C13 127.3(2) . . ?
B014 O2 B016 125.5(2) . . ?
N1 N2 B017 109.48(17) . . ?
C2 N2 N1 110.69(17) . . ?
C2 N2 B017 138.3(2) . . ?
N2 C2 N3 112.52(19) . . ?
N2 C2 C3 125.2(2) . . ?
N3 C2 C3 122.2(2) . . ?
C12 O3 B015 111.38(18) . . ?
C2 N3 C6 119.71(18) . . ?
C2 N3 B014 110.84(17) . . ?
C6 N3 B014 129.43(18) . . ?
C4 C3 C2 117.6(2) . . ?
C7 N4 B016 128.57(19) . . ?
C11 N4 C7 120.1(2) . . ?
C11 N4 B016 111.28(18) . . ?
C3 C4 C5 120.3(2) . . ?
N6 N5 B015 108.51(18) . . ?
C11 N5 N6 110.32(17) . . ?
C11 N5 B015 141.1(2) . . ?
C6 C5 C4 120.3(2) . . ?
N5 N6 B016 110.82(18) . . ?
C12 N6 N5 108.83(17) . . ?
C12 N6 B016 140.2(2) . . ?
N3 C6 C7 119.16(19) . . ?
C5 C6 N3 119.8(2) . . ?
C5 C6 C7 121.0(2) . . ?
N4 C7 C6 119.5(2) . . ?
C8 C7 N4 120.0(2) . . ?
C8 C7 C6 120.5(2) . . ?
C7 C8 C9 119.6(2) . . ?
C10 C9 C8 120.6(2) . . ?
C9 C10 C11 117.9(2) . . ?
N4 C11 C10 121.8(2) . . ?
N5 C11 N4 112.4(2) . . ?
N5 C11 C10 125.8(2) . . ?
O3 C12 C19 119.4(2) . . ?
N6 C12 O3 114.1(2) . . ?
N6 C12 C19 126.5(2) . . ?
C14 C13 C1 123.2(2) . . ?
C14 C13 C18 119.0(2) . . ?
C18 C13 C1 117.8(2) . . ?
C15 C14 C13 120.1(2) . . ?
N1 B014 N3 95.17(17) . . ?
O2 B014 N1 112.8(2) . . ?
O2 B014 N3 113.6(2) . . ?
F3 B014 N1 109.58(19) . . ?
F3 B014 O2 115.3(2) . . ?
F3 B014 N3 108.6(2) . . ?
C14 C15 C16 120.8(2) . . ?
O3 B015 N5 97.18(17) . . ?
F5 B015 O3 111.17(19) . . ?
F5 B015 N5 112.8(2) . . ?
F5 B015 F6 110.5(2) . . ?
F6 B015 O3 111.1(2) . . ?
F6 B015 N5 113.47(19) . . ?
C17 C16 C15 119.7(2) . . ?
O2 B016 N4 113.4(2) . . ?
O2 B016 N6 112.17(19) . . ?
F4 B016 O2 115.4(2) . . ?
F4 B016 N4 110.24(18) . . ?
F4 B016 N6 108.73(19) . . ?
N6 B016 N4 94.94(17) . . ?
C18 C17 C16 120.0(2) . . ?
F1 B017 O1 110.57(19) . . ?
F1 B017 N2 113.3(2) . . ?
O1 B017 N2 97.34(17) . . ?
F2 B017 F1 110.69(19) . . ?
F2 B017 O1 111.5(2) . . ?
F2 B017 N2 112.78(19) . . ?
C17 C18 C13 120.4(2) . . ?
C20 C19 C12 122.7(2) . . ?
C20 C19 C24 119.1(2) . . ?
C24 C19 C12 118.2(2) . . ?
C21 C20 C19 119.9(2) . . ?
C22 C21 C20 120.6(2) . . ?
C21 C22 C23 119.9(2) . . ?
C24 C23 C22 120.3(2) . . ?
C23 C24 C19 120.2(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.398
_oxdiff_exptl_absorpt_empirical_full_min 0.468
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.7444(8) 5111 13017 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.2556(8) 5182 13017 nmt -1.0005 -0.0000 0.0007 0.0001 -1.0003 -0.0006
-0.2886 0.0039 0.9996

_twin_special_details            
;
Component 2 rotated by -179.9947° 
around [-0.00 -0.00 1.00] (reciprocal) or [-0.14 0.00 0.99] (direct)
;
####################################################################### 
# 
# 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_ot2405b_p-br-phboaph-dimer_auto
_database_code_depnum_ccdc_archive 'CCDC 2322220'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2024-05-02 deposited with the CCDC.	2024-05-06 downloaded from the CCDC.
;
_audit_creation_date             2024-05-01
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H14 B4 Br2 F8 N6 O2, C H2 Cl2'
_chemical_formula_sum            'C25 H16 B4 Br2 Cl2 F8 N6 O2'
_chemical_formula_weight         858.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O B F Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   7.36860(10)
_cell_length_b                   18.9186(4)
_cell_length_c                   21.9266(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.991(2)
_cell_angle_gamma                90
_cell_volume                     3054.80(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14011
_cell_measurement_temperature    100.03(11)
_cell_measurement_theta_max      75.8980
_cell_measurement_theta_min      3.0360
_shelx_estimated_absorpt_T_max   0.874
_shelx_estimated_absorpt_T_min   0.406
_exptl_absorpt_coefficient_mu    5.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.024
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20800
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.273
_diffrn_reflns_theta_min         3.086
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.03(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00 -60.00   0.50    0.05    --  -44.51 135.00 -98.00   50
  2  ω    -98.00 -73.00   0.50    0.12    -- -104.00 135.00 -98.00   50
  3  ω   -103.00 -65.00   0.50    0.12    -- -104.00  77.00 -60.00   76
  4  ω    -24.00  15.00   0.50    0.05    --  -44.51  19.00 -90.00   78
  5  ω    -23.00  34.00   0.50    0.05    --  -44.51  19.00-180.00  114
  6  ω   -131.00 -86.00   0.50    0.12    -- -104.00 -30.00 -90.00   90
  7  ω   -173.00-147.00   0.50    0.12    -- -104.00 -30.00 -90.00   52
  8  ω   -111.00 -80.00   0.50    0.05    --  -44.51-135.00-164.00   62
  9  ω   -146.00-120.00   0.50    0.12    -- -104.00-135.00-164.00   52
 10  ω   -122.00 -94.00   0.50    0.12    -- -104.00-134.00  15.00   56
 11  ω   -109.00 -69.00   0.50    0.05    --  -44.51-134.00  15.00   80
 12  ω    -33.00  25.00   0.50    0.05    --   44.51 -19.00 -30.00  116
 13  ω     41.00  73.00   0.50    0.12    --  108.18 -61.00  60.00   64
 14  ω     35.00  71.00   0.50    0.12    --  108.18 -61.00  30.00   72
 15  ω     38.00  91.00   0.50    0.12    --  108.18 -77.00-120.00  106
 16  ω     47.00  72.00   0.50    0.12    --  108.18 -61.00-120.00   50
 17  ω     38.00  66.00   0.50    0.12    --  108.18 -61.00-180.00   56
 18  ω     66.00 105.00   0.50    0.12    --  108.18 -94.00-150.00   78
 19  ω     41.00 119.00   0.50    0.12    --  108.18-135.00-164.00  156
 20  ω     52.00 102.00   0.50    0.05    --   44.51-135.00-164.00  100
 21  ω     54.00  80.00   0.50    0.05    --   44.51-134.00  15.00   52
 22  ω     74.00 105.00   0.50    0.12    --  108.18-134.00  15.00   62
 23  ω     90.00 177.00   0.50    0.12    --  108.18  61.00-180.00  174
 24  ω    101.00 126.00   0.50    0.12    --  108.18 135.00 -98.00   50
 25  ω     78.00 122.00   0.50    0.12    --  108.18 134.00  82.00   88
 26  ω     81.00 177.00   0.50    0.12    --  108.18  77.00 150.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0002472000
_diffrn_orient_matrix_UB_12      -0.0536833000
_diffrn_orient_matrix_UB_13      0.0528241000
_diffrn_orient_matrix_UB_21      0.0015558000
_diffrn_orient_matrix_UB_22      -0.0612283000
_diffrn_orient_matrix_UB_23      -0.0463293000
_diffrn_orient_matrix_UB_31      0.2091521000
_diffrn_orient_matrix_UB_32      0.0005068000
_diffrn_orient_matrix_UB_33      0.0027603000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5518
_reflns_number_total             6127
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         6127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.043
_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)+(0.0465P)²+1.6156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0830
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16), C20(H20), C21(H21), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.83728(3) 0.45038(2) 0.14197(2) 0.03332(8) Uani 1 1 d . . . . .
Br2 Br -0.18510(3) 0.49087(2) 0.38332(2) 0.02449(8) Uani 1 1 d . . . . .
F1 F 1.06970(19) 0.64720(7) 0.22960(6) 0.0281(3) Uani 1 1 d . . . . .
F2 F 1.22594(16) 0.74120(7) 0.19410(6) 0.0259(3) Uani 1 1 d . . . . .
F3 F 0.74460(17) 0.61712(7) 0.01671(6) 0.0249(3) Uani 1 1 d . . . . .
F4 F 0.91491(16) 0.70175(7) -0.02548(5) 0.0221(3) Uani 1 1 d . . . . .
F5 F 0.60708(17) 0.65793(7) 0.28877(5) 0.0232(3) Uani 1 1 d . . . . .
F6 F 0.46632(15) 0.76065(7) 0.31317(5) 0.0230(3) Uani 1 1 d . . . . .
F7 F 0.91792(16) 0.64737(7) 0.50275(6) 0.0223(3) Uani 1 1 d . . . . .
F8 F 0.76384(16) 0.74041(7) 0.53880(5) 0.0212(2) Uani 1 1 d . . . . .
O1 O 1.0666(2) 0.61050(8) 0.03112(6) 0.0207(3) Uani 1 1 d . . . . .
O2 O 0.59662(19) 0.64757(8) 0.48895(6) 0.0200(3) Uani 1 1 d . . . . .
N1 N 0.8950(2) 0.74176(9) 0.17937(7) 0.0154(3) Uani 1 1 d . . . . .
N2 N 1.0668(2) 0.66636(9) 0.11920(7) 0.0164(3) Uani 1 1 d . . . . .
N3 N 0.9181(2) 0.69446(10) 0.08613(7) 0.0185(3) Uani 1 1 d . . . . .
N4 N 0.7951(2) 0.75452(9) 0.33100(7) 0.0148(3) Uani 1 1 d . . . . .
N5 N 0.6067(2) 0.69281(9) 0.39662(7) 0.0164(3) Uani 1 1 d . . . . .
N6 N 0.7572(2) 0.72202(10) 0.42809(7) 0.0180(3) Uani 1 1 d . . . . .
C1 C 0.8082(3) 0.78091(10) 0.22221(9) 0.0157(4) Uani 1 1 d . . . . .
C2 C 0.6511(3) 0.81623(11) 0.20699(9) 0.0182(4) Uani 1 1 d . . . . .
H2 H 0.591868 0.843590 0.236688 0.022 Uiso 1 1 calc R U . . .
C3 C 0.5775(3) 0.81168(11) 0.14652(9) 0.0201(4) Uani 1 1 d . . . . .
H3 H 0.468801 0.836330 0.135660 0.024 Uiso 1 1 calc R U . . .
C4 C 0.6616(3) 0.77217(11) 0.10384(9) 0.0199(4) Uani 1 1 d . . . . .
H4 H 0.613214 0.768830 0.063216 0.024 Uiso 1 1 calc R U . . .
C5 C 0.8219(3) 0.73658(11) 0.12173(9) 0.0167(4) Uani 1 1 d . . . . .
C6 C 1.1461(3) 0.62002(11) 0.08458(9) 0.0180(4) Uani 1 1 d . . . . .
C7 C 1.3109(3) 0.58041(11) 0.10117(9) 0.0176(4) Uani 1 1 d . . . . .
C8 C 1.4344(3) 0.60286(12) 0.14718(9) 0.0214(4) Uani 1 1 d . . . . .
H8 H 1.410827 0.644567 0.169700 0.026 Uiso 1 1 calc R U . . .
C9 C 1.5909(3) 0.56422(12) 0.15983(10) 0.0233(4) Uani 1 1 d . . . . .
H9 H 1.675364 0.578966 0.190978 0.028 Uiso 1 1 calc R U . . .
C10 C 1.6220(3) 0.50338(12) 0.12605(10) 0.0227(4) Uani 1 1 d . . . . .
C11 C 1.5015(3) 0.48016(12) 0.08060(10) 0.0224(4) Uani 1 1 d . . . . .
H11 H 1.525555 0.438262 0.058411 0.027 Uiso 1 1 calc R U . . .
C12 C 1.3456(3) 0.51885(11) 0.06796(9) 0.0204(4) Uani 1 1 d . . . . .
H12 H 1.261848 0.503700 0.036727 0.024 Uiso 1 1 calc R U . . .
C13 C 0.8920(3) 0.78367(10) 0.28505(9) 0.0157(4) Uani 1 1 d . . . . .
C14 C 1.0559(3) 0.81498(11) 0.29802(9) 0.0184(4) Uani 1 1 d . . . . .
H14 H 1.124906 0.833888 0.266050 0.022 Uiso 1 1 calc R U . . .
C15 C 1.1226(3) 0.81915(11) 0.35922(9) 0.0191(4) Uani 1 1 d . . . . .
H15 H 1.234593 0.842377 0.368381 0.023 Uiso 1 1 calc R U . . .
C16 C 1.0272(3) 0.79002(11) 0.40513(9) 0.0189(4) Uani 1 1 d . . . . .
H16 H 1.070473 0.792569 0.446397 0.023 Uiso 1 1 calc R U . . .
C17 C 0.8631(3) 0.75620(10) 0.38921(9) 0.0156(4) Uani 1 1 d . . . . .
C18 C 0.5209(3) 0.65231(11) 0.43437(9) 0.0170(4) Uani 1 1 d . . . . .
C19 C 0.3534(3) 0.61375(11) 0.41969(9) 0.0178(4) Uani 1 1 d . . . . .
C20 C 0.2382(3) 0.63239(11) 0.37032(9) 0.0200(4) Uani 1 1 d . . . . .
H20 H 0.269556 0.670242 0.344231 0.024 Uiso 1 1 calc R U . . .
C21 C 0.0780(3) 0.59541(11) 0.35961(9) 0.0204(4) Uani 1 1 d . . . . .
H21 H -0.002726 0.608245 0.326737 0.025 Uiso 1 1 calc R U . . .
C22 C 0.0372(3) 0.53945(11) 0.39747(9) 0.0190(4) Uani 1 1 d . . . . .
C23 C 0.1521(3) 0.51848(11) 0.44554(10) 0.0208(4) Uani 1 1 d . . . . .
H23 H 0.123974 0.478609 0.469797 0.025 Uiso 1 1 calc R U . . .
C24 C 0.3095(3) 0.55728(11) 0.45727(9) 0.0197(4) Uani 1 1 d . . . . .
H24 H 0.387584 0.545275 0.491065 0.024 Uiso 1 1 calc R U . . .
B1 B 1.0786(3) 0.69824(13) 0.18606(10) 0.0179(4) Uani 1 1 d . . . . .
B2 B 0.9008(3) 0.65684(13) 0.02307(10) 0.0195(4) Uani 1 1 d . . . . .
B3 B 0.6055(3) 0.71484(12) 0.32675(10) 0.0169(4) Uani 1 1 d . . . . .
B4 B 0.7692(3) 0.69049(13) 0.49372(10) 0.0184(4) Uani 1 1 d . . . . .
Cl1 Cl 0.41210(7) 0.41056(3) 0.35046(3) 0.02989(13) Uani 1 1 d . . . . .
Cl2 Cl 0.20381(8) 0.47048(3) 0.24661(3) 0.03628(14) Uani 1 1 d . . . . .
C25 C 0.4094(3) 0.47337(14) 0.29042(13) 0.0335(5) Uani 1 1 d . . . . .
H25A H 0.426039 0.521322 0.307811 0.040 Uiso 1 1 calc R U . . .
H25B H 0.512050 0.463878 0.263625 0.040 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.899(2) . ?
Br2 C22 1.894(2) . ?
F1 B1 1.361(3) . ?
F2 B1 1.363(3) . ?
F3 B2 1.377(3) . ?
F4 B2 1.369(3) . ?
F5 B3 1.362(3) . ?
F6 B3 1.367(3) . ?
F7 B4 1.375(3) . ?
F8 B4 1.369(3) . ?
O1 C6 1.305(2) . ?
O1 B2 1.509(3) . ?
O2 C18 1.306(2) . ?
O2 B4 1.510(3) . ?
N1 C1 1.372(3) . ?
N1 C5 1.360(3) . ?
N1 B1 1.586(3) . ?
N2 N3 1.397(2) . ?
N2 C6 1.311(3) . ?
N2 B1 1.585(3) . ?
N3 C5 1.336(3) . ?
N3 B2 1.556(3) . ?
N4 C13 1.370(3) . ?
N4 C17 1.355(2) . ?
N4 B3 1.586(3) . ?
N5 N6 1.399(2) . ?
N5 C18 1.307(3) . ?
N5 B3 1.587(3) . ?
N6 C17 1.342(3) . ?
N6 B4 1.557(3) . ?
C1 C2 1.368(3) . ?
C1 C13 1.491(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.418(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.363(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.403(3) . ?
C6 C7 1.462(3) . ?
C7 C8 1.401(3) . ?
C7 C12 1.402(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(3) . ?
C10 C11 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.366(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.415(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.364(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.402(3) . ?
C18 C19 1.460(3) . ?
C19 C20 1.398(3) . ?
C19 C24 1.394(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.385(3) . ?
C22 C23 1.387(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.389(3) . ?
C24 H24 0.9500 . ?
Cl1 C25 1.773(3) . ?
Cl2 C25 1.766(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 B2 111.18(16) . . ?
C18 O2 B4 111.02(15) . . ?
C1 N1 B1 129.30(16) . . ?
C5 N1 C1 119.74(17) . . ?
C5 N1 B1 110.96(16) . . ?
N3 N2 B1 110.61(15) . . ?
C6 N2 N3 108.15(16) . . ?
C6 N2 B1 141.18(17) . . ?
N2 N3 B2 109.01(16) . . ?
C5 N3 N2 110.24(16) . . ?
C5 N3 B2 139.70(17) . . ?
C13 N4 B3 128.87(16) . . ?
C17 N4 C13 119.85(17) . . ?
C17 N4 B3 111.26(16) . . ?
N6 N5 B3 110.49(15) . . ?
C18 N5 N6 108.16(16) . . ?
C18 N5 B3 141.12(17) . . ?
N5 N6 B4 108.86(15) . . ?
C17 N6 N5 110.22(16) . . ?
C17 N6 B4 139.09(17) . . ?
N1 C1 C13 117.63(17) . . ?
C2 C1 N1 120.49(18) . . ?
C2 C1 C13 121.88(18) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.46(19) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.46(19) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 117.99(19) . . ?
C5 C4 H4 121.0 . . ?
N1 C5 C4 121.84(18) . . ?
N3 C5 N1 112.62(17) . . ?
N3 C5 C4 125.54(18) . . ?
O1 C6 N2 114.66(18) . . ?
O1 C6 C7 119.73(18) . . ?
N2 C6 C7 125.61(18) . . ?
C8 C7 C6 122.47(19) . . ?
C8 C7 C12 120.02(19) . . ?
C12 C7 C6 117.49(18) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.8(2) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 Br1 119.40(17) . . ?
C11 C10 Br1 118.42(16) . . ?
C11 C10 C9 122.2(2) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.0(2) . . ?
C12 C11 H11 120.5 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.1(2) . . ?
C11 C12 H12 120.0 . . ?
N4 C13 C1 117.10(17) . . ?
C14 C13 N4 120.05(18) . . ?
C14 C13 C1 122.83(17) . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.80(18) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.42(19) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 121.2 . . ?
C15 C16 C17 117.58(18) . . ?
C17 C16 H16 121.2 . . ?
N4 C17 C16 122.20(18) . . ?
N6 C17 N4 112.50(17) . . ?
N6 C17 C16 125.30(18) . . ?
O2 C18 N5 114.83(18) . . ?
O2 C18 C19 119.92(17) . . ?
N5 C18 C19 125.25(18) . . ?
C20 C19 C18 122.06(18) . . ?
C24 C19 C18 117.67(18) . . ?
C24 C19 C20 120.27(19) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.66(19) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.09(19) . . ?
C22 C21 H21 120.5 . . ?
C21 C22 Br2 118.51(15) . . ?
C21 C22 C23 122.31(19) . . ?
C23 C22 Br2 119.17(16) . . ?
C22 C23 H23 120.9 . . ?
C22 C23 C24 118.26(19) . . ?
C24 C23 H23 120.9 . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.33(19) . . ?
C23 C24 H24 119.8 . . ?
F1 B1 F2 112.94(17) . . ?
F1 B1 N1 111.82(17) . . ?
F1 B1 N2 112.12(17) . . ?
F2 B1 N1 112.05(18) . . ?
F2 B1 N2 111.37(17) . . ?
N2 B1 N1 95.33(14) . . ?
F3 B2 O1 111.42(18) . . ?
F3 B2 N3 112.47(17) . . ?
F4 B2 F3 110.22(17) . . ?
F4 B2 O1 111.61(17) . . ?
F4 B2 N3 113.63(18) . . ?
O1 B2 N3 96.92(15) . . ?
F5 B3 F6 112.97(17) . . ?
F5 B3 N4 112.58(17) . . ?
F5 B3 N5 112.51(17) . . ?
F6 B3 N4 111.42(17) . . ?
F6 B3 N5 110.83(16) . . ?
N4 B3 N5 95.29(14) . . ?
F7 B4 O2 110.86(18) . . ?
F7 B4 N6 112.33(17) . . ?
F8 B4 F7 110.39(17) . . ?
F8 B4 O2 112.07(17) . . ?
F8 B4 N6 113.63(18) . . ?
O2 B4 N6 96.95(15) . . ?
Cl1 C25 H25A 109.3 . . ?
Cl1 C25 H25B 109.3 . . ?
Cl2 C25 Cl1 111.73(14) . . ?
Cl2 C25 H25A 109.3 . . ?
Cl2 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.161
_oxdiff_exptl_absorpt_empirical_full_min 0.802
####################################################################### 
# 
# 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_ono144
_database_code_depnum_ccdc_archive 'CCDC 2322219'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-05-06 downloaded from the CCDC.
;
_audit_creation_date             2023-03-30
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H26 B4 F8 N8 O2'
_chemical_formula_sum            'C28 H26 B4 F8 N8 O2'
_chemical_formula_weight         701.81
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O B F '
_chemical_oxdiff_usercomment     '123K dimeaniline-BOAPH-dimer Ch2Cl2 hexane'
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'
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                   9.2962(7)
_cell_length_b                   9.8661(7)
_cell_length_c                   17.0113(12)
_cell_angle_alpha                84.337(6)
_cell_angle_beta                 83.855(6)
_cell_angle_gamma                80.627(6)
_cell_volume                     1525.30(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2338
_cell_measurement_temperature    123
_cell_measurement_theta_max      23.1350
_cell_measurement_theta_min      2.4990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16242
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.508
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   55.00    --   30.00  54.00 150.00  193
  2  ω    -74.00 119.00   1.00   55.00    --   30.00  54.00 150.00  193
  3  ω    -67.00 119.00   1.00   55.00    --   30.00  54.00   0.00  186
  4  ω      1.00  31.00   1.00   55.00    --   30.00  54.00 -90.00   30
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0059968000
_diffrn_orient_matrix_UB_12      0.0675867000
_diffrn_orient_matrix_UB_13      0.0087136000
_diffrn_orient_matrix_UB_21      0.0626571000
_diffrn_orient_matrix_UB_22      -0.0265754000
_diffrn_orient_matrix_UB_23      0.0203300000
_diffrn_orient_matrix_UB_31      0.0455002000
_diffrn_orient_matrix_UB_32      0.0084775000
_diffrn_orient_matrix_UB_33      -0.0357995000
_diffrn_oxdiff_ac3_digest_frames 
;
015ec8f4c7cbddb2aed54f321b57d3d4de00602eef4
;
_diffrn_oxdiff_ac3_digest_hkl    
;
014410e634af23552db555b580dcbb398a78b1
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3800
_reflns_number_total             6239
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         6239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.019
_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)+(0.0600P)²+0.8130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1479
_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:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C11(H11), C12(H12), C16(H16),
 C17(H17), C18(H18), C22(H22), C23(H23), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C27(H27A,H27B,H27C), 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
B1 B 0.9034(4) 0.4921(3) 0.13614(19) 0.0254(7) Uani 1 1 d . . . . .
B2 B 0.8221(4) 0.8416(3) 0.0160(2) 0.0303(8) Uani 1 1 d . . . . .
B3 B 0.8611(4) 0.5369(3) 0.40230(19) 0.0265(7) Uani 1 1 d . . . . .
B4 B 0.7882(4) 0.2073(3) 0.5305(2) 0.0306(8) Uani 1 1 d . . . . .
C1 C 1.0488(3) 0.5674(3) 0.24759(16) 0.0257(6) Uani 1 1 d . . . . .
C2 C 1.1079(3) 0.6691(3) 0.27574(17) 0.0312(7) Uani 1 1 d . . . . .
H2 H 1.159083 0.650536 0.322011 0.037 Uiso 1 1 calc R . . . .
C3 C 1.0923(3) 0.8020(3) 0.23547(17) 0.0313(7) Uani 1 1 d . . . . .
H3 H 1.131372 0.873151 0.255824 0.038 Uiso 1 1 calc R . . . .
C4 C 1.0227(3) 0.8303(3) 0.16839(17) 0.0281(7) Uani 1 1 d . . . . .
H4 H 1.012160 0.919722 0.141282 0.034 Uiso 1 1 calc R . . . .
C5 C 0.9661(3) 0.7209(3) 0.14028(17) 0.0265(6) Uani 1 1 d . . . . .
C6 C 0.7652(3) 0.6207(3) 0.00813(16) 0.0269(6) Uani 1 1 d . . . . .
C7 C 0.7082(3) 0.5130(3) -0.02565(16) 0.0276(7) Uani 1 1 d . . . . .
C8 C 0.7418(3) 0.3735(3) -0.00143(17) 0.0297(7) Uani 1 1 d . . . . .
H8 H 0.800285 0.346490 0.041622 0.036 Uiso 1 1 calc R . . . .
C9 C 0.6927(3) 0.2731(3) -0.03801(17) 0.0301(7) Uani 1 1 d . . . . .
H9 H 0.717218 0.178802 -0.019785 0.036 Uiso 1 1 calc R . . . .
C10 C 0.6061(3) 0.3101(3) -0.10258(17) 0.0303(7) Uani 1 1 d . . . . .
C11 C 0.5714(3) 0.4513(3) -0.12699(18) 0.0324(7) Uani 1 1 d . . . . .
H11 H 0.513832 0.478944 -0.170353 0.039 Uiso 1 1 calc R . . . .
C12 C 0.6201(3) 0.5505(3) -0.08872(17) 0.0293(7) Uani 1 1 d . . . . .
H12 H 0.593391 0.645190 -0.105376 0.035 Uiso 1 1 calc R . . . .
C13 C 0.4687(4) 0.2471(3) -0.2056(2) 0.0459(9) Uani 1 1 d . . . . .
H13A H 0.401106 0.332367 -0.196185 0.069 Uiso 1 1 calc GR . . . .
H13B H 0.412671 0.172644 -0.209882 0.069 Uiso 1 1 calc GR . . . .
H13C H 0.531237 0.260938 -0.254925 0.069 Uiso 1 1 calc GR . . . .
C14 C 0.6011(4) 0.0657(3) -0.11716(19) 0.0376(8) Uani 1 1 d . . . . .
H14A H 0.708082 0.044045 -0.119590 0.056 Uiso 1 1 calc GR . . . .
H14B H 0.564698 0.010496 -0.153346 0.056 Uiso 1 1 calc GR . . . .
H14C H 0.559151 0.044290 -0.062875 0.056 Uiso 1 1 calc GR . . . .
C15 C 1.0530(3) 0.4264(3) 0.28928(17) 0.0278(7) Uani 1 1 d . . . . .
C16 C 1.1392(3) 0.3113(3) 0.26271(18) 0.0330(7) Uani 1 1 d . . . . .
H16 H 1.203128 0.318126 0.215502 0.040 Uiso 1 1 calc R . . . .
C17 C 1.1330(3) 0.1821(3) 0.30571(19) 0.0366(8) Uani 1 1 d . . . . .
H17 H 1.195919 0.102744 0.288343 0.044 Uiso 1 1 calc R . . . .
C18 C 1.0372(3) 0.1699(3) 0.37227(18) 0.0340(7) Uani 1 1 d . . . . .
H18 H 1.029745 0.082916 0.400445 0.041 Uiso 1 1 calc R . . . .
C19 C 0.9501(3) 0.2918(3) 0.39720(17) 0.0283(7) Uani 1 1 d . . . . .
C20 C 0.6980(3) 0.4433(3) 0.53431(17) 0.0275(7) Uani 1 1 d . . . . .
C21 C 0.6198(3) 0.5661(3) 0.56882(16) 0.0281(7) Uani 1 1 d . . . . .
C22 C 0.5167(3) 0.5503(3) 0.63308(17) 0.0327(7) Uani 1 1 d . . . . .
H22 H 0.498346 0.460258 0.651875 0.039 Uiso 1 1 calc R . . . .
C23 C 0.4407(3) 0.6610(3) 0.67018(18) 0.0361(8) Uani 1 1 d . . . . .
H23 H 0.370635 0.646091 0.713809 0.043 Uiso 1 1 calc R . . . .
C24 C 0.4646(3) 0.7960(3) 0.64477(17) 0.0306(7) Uani 1 1 d . . . . .
C25 C 0.5693(3) 0.8122(3) 0.57887(18) 0.0354(7) Uani 1 1 d . . . . .
H25 H 0.587982 0.901972 0.559603 0.042 Uiso 1 1 calc R . . . .
C26 C 0.6441(3) 0.6999(3) 0.54255(17) 0.0333(7) Uani 1 1 d . . . . .
H26 H 0.713915 0.713401 0.498598 0.040 Uiso 1 1 calc R . . . .
C27 C 0.2854(4) 0.8891(4) 0.7500(2) 0.0472(9) Uani 1 1 d . . . . .
H27A H 0.200688 0.856055 0.732982 0.071 Uiso 1 1 calc GR . . . .
H27B H 0.253158 0.976848 0.773648 0.071 Uiso 1 1 calc GR . . . .
H27C H 0.331411 0.820985 0.789296 0.071 Uiso 1 1 calc GR . . . .
C28 C 0.3805(4) 1.0455(3) 0.6394(2) 0.0491(9) Uani 1 1 d . . . . .
H28A H 0.478235 1.072167 0.629005 0.074 Uiso 1 1 calc GR . . . .
H28B H 0.317188 1.112075 0.671967 0.074 Uiso 1 1 calc GR . . . .
H28C H 0.338780 1.044334 0.588993 0.074 Uiso 1 1 calc GR . . . .
F1 F 0.78758(17) 0.44852(16) 0.18394(9) 0.0318(4) Uani 1 1 d . . . . .
F2 F 0.99967(17) 0.38314(16) 0.10962(9) 0.0313(4) Uani 1 1 d . . . . .
F3 F 0.72924(19) 0.94312(17) 0.05319(10) 0.0389(4) Uani 1 1 d . . . . .
F4 F 0.91980(19) 0.89672(18) -0.03949(10) 0.0386(4) Uani 1 1 d . . . . .
F5 F 0.76161(18) 0.61378(16) 0.35528(9) 0.0329(4) Uani 1 1 d . . . . .
F6 F 0.94291(18) 0.61775(17) 0.43469(9) 0.0337(4) Uani 1 1 d . . . . .
F7 F 0.7158(2) 0.10925(18) 0.50766(10) 0.0430(5) Uani 1 1 d . . . . .
F8 F 0.8929(2) 0.14651(17) 0.57993(10) 0.0394(4) Uani 1 1 d . . . . .
N1 N 0.9795(2) 0.5929(2) 0.17898(13) 0.0247(5) Uani 1 1 d . . . . .
N2 N 0.8948(3) 0.7302(2) 0.07556(14) 0.0295(6) Uani 1 1 d . . . . .
N3 N 0.8505(3) 0.6017(2) 0.06701(14) 0.0286(6) Uani 1 1 d . . . . .
N4 N 0.5586(3) 0.2110(3) -0.14034(15) 0.0360(6) Uani 1 1 d . . . . .
N5 N 0.9612(3) 0.4168(2) 0.35801(13) 0.0256(5) Uani 1 1 d . . . . .
N6 N 0.7892(3) 0.4382(2) 0.46869(13) 0.0269(5) Uani 1 1 d . . . . .
N7 N 0.8498(3) 0.3001(2) 0.45978(14) 0.0299(6) Uani 1 1 d . . . . .
N8 N 0.3912(3) 0.9089(3) 0.68133(15) 0.0383(6) Uani 1 1 d . . . . .
O1 O 0.7395(2) 0.7489(2) -0.02231(11) 0.0303(5) Uani 1 1 d . . . . .
O2 O 0.6858(2) 0.3200(2) 0.56978(11) 0.0323(5) 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
B1 F1 1.379(3) . ?
B1 F2 1.363(4) . ?
B1 N1 1.582(4) . ?
B1 N3 1.579(4) . ?
B2 F3 1.369(4) . ?
B2 F4 1.374(4) . ?
B2 N2 1.542(4) . ?
B2 O1 1.519(4) . ?
B3 F5 1.372(4) . ?
B3 F6 1.375(4) . ?
B3 N5 1.583(4) . ?
B3 N6 1.582(4) . ?
B4 F7 1.372(4) . ?
B4 F8 1.378(4) . ?
B4 N7 1.556(4) . ?
B4 O2 1.501(4) . ?
C1 C2 1.368(4) . ?
C1 C15 1.494(4) . ?
C1 N1 1.375(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.411(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.355(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.418(4) . ?
C5 N1 1.359(3) . ?
C5 N2 1.333(4) . ?
C6 C7 1.452(4) . ?
C6 N3 1.324(4) . ?
C6 O1 1.313(3) . ?
C7 C8 1.392(4) . ?
C7 C12 1.404(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.415(4) . ?
C10 C11 1.409(4) . ?
C10 N4 1.375(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 N4 1.442(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 N4 1.451(4) . ?
C15 C16 1.365(4) . ?
C15 N5 1.377(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.412(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.372(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.411(4) . ?
C19 N5 1.357(3) . ?
C19 N7 1.338(4) . ?
C20 C21 1.450(4) . ?
C20 N6 1.328(4) . ?
C20 O2 1.319(3) . ?
C21 C22 1.389(4) . ?
C21 C26 1.397(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.371(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.405(4) . ?
C24 C25 1.418(4) . ?
C24 N8 1.375(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.373(4) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C27 N8 1.464(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C28 N8 1.455(4) . ?
N2 N3 1.420(3) . ?
N6 N7 1.403(3) . ?

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
F1 B1 N1 111.4(2) . . ?
F1 B1 N3 112.0(2) . . ?
F2 B1 F1 111.2(2) . . ?
F2 B1 N1 112.6(2) . . ?
F2 B1 N3 113.0(2) . . ?
N3 B1 N1 95.8(2) . . ?
F3 B2 F4 111.1(3) . . ?
F3 B2 N2 112.1(3) . . ?
F3 B2 O1 111.9(3) . . ?
F4 B2 N2 113.8(3) . . ?
F4 B2 O1 110.1(2) . . ?
O1 B2 N2 97.1(2) . . ?
F5 B3 F6 112.0(2) . . ?
F5 B3 N5 112.5(2) . . ?
F5 B3 N6 113.1(2) . . ?
F6 B3 N5 111.8(2) . . ?
F6 B3 N6 111.0(2) . . ?
N6 B3 N5 95.3(2) . . ?
F7 B4 F8 110.0(3) . . ?
F7 B4 N7 113.5(3) . . ?
F7 B4 O2 112.3(3) . . ?
F8 B4 N7 113.1(3) . . ?
F8 B4 O2 110.6(3) . . ?
O2 B4 N7 96.8(2) . . ?
C2 C1 C15 122.7(3) . . ?
C2 C1 N1 120.3(3) . . ?
N1 C1 C15 117.0(2) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.3(3) . . ?
C5 C4 H4 121.4 . . ?
N1 C5 C4 121.8(3) . . ?
N2 C5 C4 125.4(3) . . ?
N2 C5 N1 112.8(2) . . ?
N3 C6 C7 125.5(3) . . ?
O1 C6 C7 120.3(3) . . ?
O1 C6 N3 114.1(2) . . ?
C8 C7 C6 123.6(3) . . ?
C8 C7 C12 117.9(3) . . ?
C12 C7 C6 118.4(3) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 C7 122.1(3) . . ?
C9 C8 H8 119.0 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 117.8(3) . . ?
N4 C10 C9 120.8(3) . . ?
N4 C10 C11 121.4(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 H12 119.5 . . ?
C11 C12 C7 120.9(3) . . ?
C11 C12 H12 119.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
C16 C15 C1 124.1(3) . . ?
C16 C15 N5 120.2(3) . . ?
N5 C15 C1 115.8(2) . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.7(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 121.3 . . ?
C17 C18 C19 117.3(3) . . ?
C19 C18 H18 121.3 . . ?
N5 C19 C18 121.8(3) . . ?
N7 C19 C18 125.9(3) . . ?
N7 C19 N5 112.3(2) . . ?
N6 C20 C21 126.9(2) . . ?
O2 C20 C21 120.4(2) . . ?
O2 C20 N6 112.7(3) . . ?
C22 C21 C20 118.3(3) . . ?
C22 C21 C26 117.7(3) . . ?
C26 C21 C20 124.0(3) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 C21 121.9(3) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 H23 119.5 . . ?
C22 C23 C24 121.1(3) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 C25 117.0(3) . . ?
N8 C24 C23 122.4(3) . . ?
N8 C24 C25 120.5(3) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 C24 120.9(3) . . ?
C26 C25 H25 119.6 . . ?
C21 C26 H26 119.3 . . ?
C25 C26 C21 121.4(3) . . ?
C25 C26 H26 119.3 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N8 C27 H27A 109.5 . . ?
N8 C27 H27B 109.5 . . ?
N8 C27 H27C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N8 C28 H28A 109.5 . . ?
N8 C28 H28B 109.5 . . ?
N8 C28 H28C 109.5 . . ?
C1 N1 B1 128.9(2) . . ?
C5 N1 B1 111.3(2) . . ?
C5 N1 C1 119.8(2) . . ?
C5 N2 B2 139.3(2) . . ?
C5 N2 N3 109.9(2) . . ?
N3 N2 B2 109.6(2) . . ?
C6 N3 B1 141.7(2) . . ?
C6 N3 N2 107.5(2) . . ?
N2 N3 B1 110.2(2) . . ?
C10 N4 C13 121.5(3) . . ?
C10 N4 C14 120.8(3) . . ?
C13 N4 C14 117.7(2) . . ?
C15 N5 B3 128.5(2) . . ?
C19 N5 B3 111.4(2) . . ?
C19 N5 C15 120.1(2) . . ?
C20 N6 B3 140.6(2) . . ?
C20 N6 N7 108.5(2) . . ?
N7 N6 B3 110.6(2) . . ?
C19 N7 B4 140.2(3) . . ?
C19 N7 N6 110.2(2) . . ?
N6 N7 B4 109.2(2) . . ?
C24 N8 C27 119.4(3) . . ?
C24 N8 C28 120.2(3) . . ?
C28 N8 C27 117.4(3) . . ?
C6 O1 B2 111.6(2) . . ?
C20 O2 B4 112.5(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.164
_oxdiff_exptl_absorpt_empirical_full_min 0.917
####################################################################### 
# 
# 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_furuta004
_database_code_depnum_ccdc_archive 'CCDC 2322221'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-05-06 downloaded from the CCDC.
;
_audit_creation_date             2022-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H14 B4 Br2 F6 N6 O3'
_chemical_formula_sum            'C24 H14 B4 Br2 F6 N6 O3'
_chemical_formula_weight         751.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'H B C N O F Cl Br'
_chemical_oxdiff_usercomment     p-Br-BOAPH-dimer-BOB
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.1074(11)
_cell_length_b                   10.5772(17)
_cell_length_c                   15.807(3)
_cell_angle_alpha                91.309(14)
_cell_angle_beta                 91.058(14)
_cell_angle_gamma                99.216(13)
_cell_volume                     1337.3(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1078
_cell_measurement_temperature    123
_cell_measurement_theta_max      23.2870
_cell_measurement_theta_min      2.8140
_shelx_estimated_absorpt_T_max   0.860
_shelx_estimated_absorpt_T_min   0.455
_exptl_absorpt_coefficient_mu    3.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1101
_diffrn_reflns_av_unetI/netI     0.1811
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12044
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.578
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   76.10    --   30.00  54.00 120.00  193
  2  ω    -74.00 119.00   1.00   76.10    --   30.00  54.00   0.00  193
  3  ω      7.00  34.00   1.00   76.10    --   30.00  54.00   0.00   27
  4  ω    -70.00  31.00   1.00   76.10    --   30.00  54.00-120.00  101
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0878258000
_diffrn_orient_matrix_UB_12      0.0094745000
_diffrn_orient_matrix_UB_13      0.0070333000
_diffrn_orient_matrix_UB_21      -0.0113084000
_diffrn_orient_matrix_UB_22      0.0130593000
_diffrn_orient_matrix_UB_23      0.0435360000
_diffrn_orient_matrix_UB_31      -0.0042935000
_diffrn_orient_matrix_UB_32      -0.0660166000
_diffrn_orient_matrix_UB_33      0.0084131000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2623
_reflns_number_total             5464
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.421
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5464
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1673
_refine_ls_R_factor_gt           0.0756
_refine_ls_restrained_S_all      0.987
_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)+(0.0432P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1877
_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:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C20(H20), C21(H21), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.05989(10) 0.81524(10) 0.08826(7) 0.0487(3) Uani 1 1 d . . . . .
Br2 Br 0.24596(11) 0.64854(10) -0.04912(7) 0.0496(3) Uani 1 1 d . . . . .
F1 F 0.4312(5) 0.2933(4) 0.4564(3) 0.0364(13) Uani 1 1 d . . . . .
F2 F 0.6121(5) 0.2001(4) 0.3783(3) 0.0374(13) Uani 1 1 d . . . . .
F3 F 0.9093(5) 0.6330(4) 0.2792(3) 0.0363(12) Uani 1 1 d . . . . .
F4 F 0.6247(5) 0.8937(4) 0.4087(3) 0.0347(12) Uani 1 1 d . . . . .
F5 F 0.9197(6) 1.2790(4) 0.2512(3) 0.0408(13) Uani 1 1 d . . . . .
F6 F 1.0334(5) 1.1545(5) 0.1575(3) 0.0445(14) Uani 1 1 d . . . . .
O1 O 0.4499(6) 0.3336(5) 0.3069(4) 0.0345(15) Uani 1 1 d . . . . .
O2 O 0.6828(6) 0.7387(5) 0.3099(4) 0.0339(15) Uani 1 1 d . . . . .
O3 O 0.7378(6) 1.1157(5) 0.1764(4) 0.0344(15) Uani 1 1 d . . . . .
N1 N 0.6495(7) 0.5027(6) 0.3214(4) 0.0276(17) Uani 1 1 d . . . . .
N2 N 0.6634(7) 0.4353(6) 0.3951(4) 0.0290(17) Uani 1 1 d . . . . .
N3 N 0.8191(7) 0.6269(6) 0.4238(4) 0.0254(16) Uani 1 1 d . . . . .
N4 N 0.9218(7) 0.8947(6) 0.3768(4) 0.0297(17) Uani 1 1 d . . . . .
N5 N 0.8995(7) 1.0509(6) 0.2815(5) 0.0329(18) Uani 1 1 d . . . . .
N6 N 0.7417(7) 0.9744(6) 0.2770(4) 0.0278(17) Uani 1 1 d . . . . .
C1 C 0.2995(10) 0.4390(8) 0.1665(6) 0.039(2) Uani 1 1 d . . . . .
H1 H 0.234456 0.373312 0.197158 0.047 Uiso 1 1 calc R . . . .
C2 C 0.2350(11) 0.4841(9) 0.0945(6) 0.046(3) Uani 1 1 d . . . . .
H2 H 0.125194 0.449205 0.075127 0.055 Uiso 1 1 calc R . . . .
C3 C 0.3302(11) 0.5813(9) 0.0494(6) 0.039(2) Uani 1 1 d . . . . .
C4 C 0.4940(11) 0.6305(8) 0.0772(6) 0.037(2) Uani 1 1 d . . . . .
H4 H 0.560070 0.695680 0.046616 0.044 Uiso 1 1 calc R . . . .
C5 C 0.5571(10) 0.5838(8) 0.1483(6) 0.038(2) Uani 1 1 d . . . . .
H5 H 0.668553 0.615986 0.166466 0.045 Uiso 1 1 calc R . . . .
C6 C 0.4618(9) 0.4902(8) 0.1945(5) 0.030(2) Uani 1 1 d . . . . .
C7 C 0.5232(9) 0.4429(7) 0.2740(6) 0.030(2) Uani 1 1 d . . . . .
C8 C 0.7521(9) 0.5106(8) 0.4555(6) 0.027(2) Uani 1 1 d . . . . .
C9 C 0.7828(9) 0.4789(8) 0.5390(6) 0.033(2) Uani 1 1 d . . . . .
H9 H 0.734224 0.398429 0.560226 0.039 Uiso 1 1 calc R . . . .
C10 C 0.8857(9) 0.5675(8) 0.5902(6) 0.032(2) Uani 1 1 d . . . . .
H10 H 0.906040 0.548600 0.647566 0.038 Uiso 1 1 calc R . . . .
C11 C 0.9607(9) 0.6860(7) 0.5577(5) 0.0257(19) Uani 1 1 d . . . . .
H11 H 1.035127 0.745144 0.592114 0.031 Uiso 1 1 calc R . . . .
C12 C 0.9240(8) 0.7146(8) 0.4752(6) 0.026(2) Uani 1 1 d . . . . .
C13 C 1.0059(9) 0.8357(7) 0.4365(5) 0.028(2) Uani 1 1 d . . . . .
C14 C 1.1700(8) 0.8830(7) 0.4573(5) 0.028(2) Uani 1 1 d . . . . .
H14 H 1.228873 0.840894 0.497623 0.034 Uiso 1 1 calc R . . . .
C15 C 1.2518(9) 0.9961(8) 0.4179(6) 0.032(2) Uani 1 1 d . . . . .
H15 H 1.363171 1.031859 0.434201 0.038 Uiso 1 1 calc R . . . .
C16 C 1.1671(9) 1.0537(7) 0.3552(5) 0.029(2) Uani 1 1 d . . . . .
H16 H 1.221452 1.124635 0.325050 0.035 Uiso 1 1 calc R . . . .
C17 C 0.9983(9) 1.0024(7) 0.3389(6) 0.029(2) Uani 1 1 d . . . . .
C18 C 0.6567(9) 1.0132(8) 0.2160(5) 0.027(2) Uani 1 1 d . . . . .
C19 C 0.4846(9) 0.9638(7) 0.1863(5) 0.0266(19) Uani 1 1 d . . . . .
C20 C 0.3866(9) 0.8631(7) 0.2260(6) 0.032(2) Uani 1 1 d . . . . .
H20 H 0.430409 0.824457 0.273295 0.039 Uiso 1 1 calc R . . . .
C21 C 0.2245(9) 0.8191(8) 0.1964(6) 0.035(2) Uani 1 1 d . . . . .
H21 H 0.156023 0.752162 0.224403 0.042 Uiso 1 1 calc R . . . .
C22 C 0.1647(9) 0.8724(8) 0.1273(6) 0.034(2) Uani 1 1 d . . . . .
C23 C 0.2594(10) 0.9707(9) 0.0854(6) 0.050(3) Uani 1 1 d . . . . .
H23 H 0.214866 1.007264 0.037420 0.060 Uiso 1 1 calc R . . . .
C24 C 0.4211(10) 1.0150(9) 0.1149(6) 0.044(3) Uani 1 1 d . . . . .
H24 H 0.489119 1.081023 0.085927 0.053 Uiso 1 1 calc R . . . .
B1 B 0.5361(11) 0.3075(9) 0.3898(7) 0.030(2) Uani 1 1 d . . . . .
B2 B 0.7697(11) 0.6377(8) 0.3278(6) 0.026(2) Uani 1 1 d . . . . .
B3 B 0.7274(10) 0.8640(10) 0.3455(7) 0.030(2) Uani 1 1 d . . . . .
B4 B 0.9116(12) 1.1584(10) 0.2148(8) 0.038(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
Br1 C22 1.911(8) . ?
Br2 C3 1.889(9) . ?
F1 B1 1.361(11) . ?
F2 B1 1.386(10) . ?
F3 B2 1.386(10) . ?
F4 B3 1.374(10) . ?
F5 B4 1.378(11) . ?
F6 B4 1.357(12) . ?
O1 C7 1.333(9) . ?
O1 B1 1.524(11) . ?
O2 B2 1.402(10) . ?
O2 B3 1.417(11) . ?
O3 C18 1.348(9) . ?
O3 B4 1.520(10) . ?
N1 N2 1.391(9) . ?
N1 C7 1.324(9) . ?
N1 B2 1.594(10) . ?
N2 C8 1.349(10) . ?
N2 B1 1.564(10) . ?
N3 C8 1.373(10) . ?
N3 C12 1.389(9) . ?
N3 B2 1.575(11) . ?
N4 C13 1.373(10) . ?
N4 C17 1.364(10) . ?
N4 B3 1.624(10) . ?
N5 N6 1.399(8) . ?
N5 C17 1.361(10) . ?
N5 B4 1.560(12) . ?
N6 C18 1.287(10) . ?
N6 B3 1.603(12) . ?
C1 H1 0.9500 . ?
C1 C2 1.370(12) . ?
C1 C6 1.401(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.400(12) . ?
C3 C4 1.405(11) . ?
C4 H4 0.9500 . ?
C4 C5 1.361(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(11) . ?
C6 C7 1.470(11) . ?
C8 C9 1.397(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(11) . ?
C10 H10 0.9500 . ?
C10 C11 1.414(11) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(11) . ?
C12 C13 1.494(11) . ?
C13 C14 1.376(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.433(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.400(11) . ?
C16 H16 0.9500 . ?
C16 C17 1.406(10) . ?
C18 C19 1.473(10) . ?
C19 C20 1.392(11) . ?
C19 C24 1.388(11) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(10) . ?
C21 H21 0.9500 . ?
C21 C22 1.358(11) . ?
C22 C23 1.379(11) . ?
C23 H23 0.9500 . ?
C23 C24 1.388(10) . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 B1 111.2(6) . . ?
B2 O2 B3 123.4(6) . . ?
C18 O3 B4 111.3(7) . . ?
N2 N1 B2 110.1(6) . . ?
C7 N1 N2 109.5(6) . . ?
C7 N1 B2 139.3(7) . . ?
N1 N2 B1 109.1(6) . . ?
C8 N2 N1 110.9(6) . . ?
C8 N2 B1 137.8(8) . . ?
C8 N3 C12 119.4(7) . . ?
C8 N3 B2 111.9(6) . . ?
C12 N3 B2 128.6(6) . . ?
C13 N4 B3 129.8(7) . . ?
C17 N4 C13 120.6(6) . . ?
C17 N4 B3 109.4(7) . . ?
N6 N5 B4 110.5(6) . . ?
C17 N5 N6 109.6(6) . . ?
C17 N5 B4 139.7(7) . . ?
N5 N6 B3 111.0(6) . . ?
C18 N6 N5 108.6(6) . . ?
C18 N6 B3 140.3(6) . . ?
C2 C1 H1 120.2 . . ?
C2 C1 C6 119.6(8) . . ?
C6 C1 H1 120.2 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(8) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 Br2 122.0(7) . . ?
C2 C3 C4 119.7(8) . . ?
C4 C3 Br2 118.3(7) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(8) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(8) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 117.7(7) . . ?
C5 C6 C1 119.8(8) . . ?
C5 C6 C7 122.5(7) . . ?
O1 C7 C6 121.7(7) . . ?
N1 C7 O1 113.0(7) . . ?
N1 C7 C6 125.3(7) . . ?
N2 C8 N3 110.9(7) . . ?
N2 C8 C9 127.3(7) . . ?
N3 C8 C9 121.8(7) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.5(8) . . ?
C10 C9 H9 120.8 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.5(8) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.1(7) . . ?
C12 C11 H11 120.5 . . ?
N3 C12 C13 117.9(7) . . ?
C11 C12 N3 120.7(7) . . ?
C11 C12 C13 121.2(7) . . ?
N4 C13 C12 120.4(7) . . ?
N4 C13 C14 120.2(7) . . ?
C14 C13 C12 119.3(7) . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.7(7) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(7) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 121.4 . . ?
C15 C16 C17 117.3(7) . . ?
C17 C16 H16 121.4 . . ?
N4 C17 C16 122.2(8) . . ?
N5 C17 N4 114.1(7) . . ?
N5 C17 C16 123.6(7) . . ?
O3 C18 C19 116.9(7) . . ?
N6 C18 O3 113.9(6) . . ?
N6 C18 C19 129.1(8) . . ?
C20 C19 C18 121.5(8) . . ?
C24 C19 C18 119.3(7) . . ?
C24 C19 C20 119.1(7) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.0(8) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.6(8) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 Br1 119.7(6) . . ?
C21 C22 C23 122.0(8) . . ?
C23 C22 Br1 118.3(7) . . ?
C22 C23 H23 120.8 . . ?
C22 C23 C24 118.5(9) . . ?
C24 C23 H23 120.8 . . ?
C19 C24 C23 120.7(8) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
F1 B1 F2 110.9(7) . . ?
F1 B1 O1 113.4(7) . . ?
F1 B1 N2 113.0(7) . . ?
F2 B1 O1 108.8(7) . . ?
F2 B1 N2 113.1(6) . . ?
O1 B1 N2 96.9(6) . . ?
F3 B2 O2 114.9(7) . . ?
F3 B2 N1 109.6(7) . . ?
F3 B2 N3 109.0(6) . . ?
O2 B2 N1 111.5(6) . . ?
O2 B2 N3 114.9(8) . . ?
N3 B2 N1 95.2(6) . . ?
F4 B3 O2 114.4(7) . . ?
F4 B3 N4 110.6(7) . . ?
F4 B3 N6 108.5(7) . . ?
O2 B3 N4 112.7(7) . . ?
O2 B3 N6 113.7(7) . . ?
N6 B3 N4 95.5(6) . . ?
F5 B4 O3 109.1(8) . . ?
F5 B4 N5 112.9(9) . . ?
F6 B4 F5 111.7(8) . . ?
F6 B4 O3 112.3(8) . . ?
F6 B4 N5 114.2(8) . . ?
O3 B4 N5 95.6(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.198
_oxdiff_exptl_absorpt_empirical_full_min 0.814
