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

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

data_0-PhBODIPY
_database_code_depnum_ccdc_archive 'CCDC 1993841'
loop_
_audit_author_name
_audit_author_address
'Yudai Suzuki'
;Keio university
Japan
;
_audit_update_record             
;
2020-03-31 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C34 H27 B Br2 N2 O2'
_chemical_formula_moiety         'C34 H27 B Br2 N2 O2'
_chemical_formula_weight         666.22
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.8301(16)
_cell_length_b                   21.461(5)
_cell_length_c                   22.842(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.018(6)
_cell_angle_gamma                90.0000
_cell_volume                     3348.2(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8616
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      25.20
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344.00
_exptl_absorpt_coefficient_mu    2.458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.017
_exptl_absorpt_correction_T_max  0.976

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            44558
_diffrn_reflns_av_unetI/netI     0.2722
_diffrn_reflns_av_R_equivalents  0.4756
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.605
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6123
_reflns_number_gt                2292
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.3008
_refine_ls_R_factor_gt           0.1675
_refine_ls_wR_factor_ref         0.4377
_refine_ls_wR_factor_gt          0.3745
_refine_ls_number_restraints     9
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6123
_refine_ls_number_parameters     375
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          1.298
_refine_diff_density_max         3.05
_refine_diff_density_min         -0.75
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 520 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(2)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.5421(5) 0.4429(2) 0.04515(16) 0.0837(15) Uani 1 1 d . . . . .
Br2 Br 0.1319(8) 0.7544(2) 0.2856(2) 0.116(2) Uani 1 1 d . . . . .
O1 O 0.618(3) 0.4012(10) 0.4025(8) 0.051(6) Uani 1 1 d . . . . .
O2 O 0.261(3) 0.3928(9) 0.3974(8) 0.048(5) Uani 1 1 d . . . . .
N1 N 0.464(3) 0.3843(11) 0.4927(13) 0.065(9) Uani 1 1 d . . . . .
N2 N 0.447(3) 0.3022(10) 0.4190(10) 0.041(5) Uani 1 1 d . . . . .
C1 C 0.482(4) 0.4429(12) 0.5190(15) 0.051(8) Uani 1 1 d . . . . .
C2 C 0.493(4) 0.4306(17) 0.5779(13) 0.055(9) Uani 1 1 d . . . . .
H2 H 0.513022 0.461960 0.606645 0.066 Uiso 1 1 calc R U . . .
C3 C 0.476(4) 0.3789(13) 0.5890(10) 0.028(6) Uani 1 1 d . . . . .
C4 C 0.453(4) 0.3412(18) 0.5361(18) 0.072(11) Uani 1 1 d . . . . .
C5 C 0.443(3) 0.2780(13) 0.5215(13) 0.038(7) Uani 1 1 d . . . . .
C6 C 0.450(3) 0.2582(10) 0.4631(12) 0.031(6) Uani 1 1 d . . . . .
C7 C 0.444(4) 0.1993(13) 0.4400(12) 0.045(8) Uani 1 1 d . . . . .
C8 C 0.429(3) 0.2049(10) 0.3802(12) 0.034(7) Uani 1 1 d . . . . .
H8 H 0.421504 0.171420 0.353043 0.041 Uiso 1 1 calc R U . . .
C9 C 0.428(3) 0.2657(10) 0.3667(10) 0.026(6) Uani 1 1 d . . . . .
C10 C 0.489(5) 0.5043(17) 0.4857(16) 0.087(12) Uani 1 1 d . . . . .
H10A H 0.368144 0.508985 0.462756 0.104 Uiso 1 1 calc R U . . .
H10B H 0.601726 0.504456 0.459290 0.104 Uiso 1 1 calc R U . . .
H10C H 0.499844 0.538843 0.513472 0.104 Uiso 1 1 calc R U . . .
C11 C 0.469(4) 0.3507(13) 0.6497(13) 0.054(8) Uani 1 1 d . . . . .
H11A H 0.447136 0.383618 0.678594 0.065 Uiso 1 1 calc R U . . .
H11B H 0.593779 0.329772 0.657956 0.065 Uiso 1 1 calc R U . . .
H11C H 0.362322 0.320275 0.651686 0.065 Uiso 1 1 calc R U . . .
C12 C 0.424(6) 0.2354(18) 0.5756(17) 0.102(14) Uani 1 1 d . . . . .
H12A H 0.286542 0.232358 0.587150 0.123 Uiso 1 1 calc R U . . .
H12B H 0.500737 0.252939 0.607968 0.123 Uiso 1 1 calc R U . . .
H12C H 0.474221 0.193793 0.566041 0.123 Uiso 1 1 calc R U . . .
C13 C 0.458(4) 0.1337(17) 0.4698(15) 0.079(11) Uani 1 1 d . . . . .
H13A H 0.485814 0.102090 0.439986 0.095 Uiso 1 1 calc R U . . .
H13B H 0.332789 0.123962 0.488886 0.095 Uiso 1 1 calc R U . . .
H13C H 0.562482 0.134014 0.499014 0.095 Uiso 1 1 calc R U . . .
C14 C 0.398(5) 0.2968(15) 0.3071(13) 0.078(12) Uani 1 1 d . . . . .
H14A H 0.321269 0.269151 0.281745 0.094 Uiso 1 1 calc R U . . .
H14B H 0.525403 0.304922 0.289058 0.094 Uiso 1 1 calc R U . . .
H14C H 0.327510 0.336198 0.312354 0.094 Uiso 1 1 calc R U . . .
C15 C 0.508(5) 0.4456(16) 0.3153(17) 0.079(11) Uani 1 1 d . . . . .
C16 C 0.634(4) 0.4146(11) 0.351(2) 0.073(13) Uani 1 1 d . . . . .
C17 C 0.809(3) 0.3927(11) 0.3125(13) 0.041(7) Uani 1 1 d . . . . .
H17 H 0.911030 0.371169 0.332242 0.049 Uiso 1 1 calc R U . . .
C18 C 0.831(4) 0.4007(12) 0.2568(13) 0.039(7) Uani 1 1 d . . . . .
H18 H 0.952776 0.389112 0.239705 0.047 Uiso 1 1 calc R U . . .
C19 C 0.685(4) 0.4256(13) 0.2199(16) 0.061(9) Uani 1 1 d . . . . .
C20 C 0.692(6) 0.4251(12) 0.1582(12) 0.061(11) Uani 1 1 d . . . . .
H20 H 0.804079 0.407737 0.139870 0.074 Uiso 1 1 calc R U . . .
C21 C 0.536(4) 0.4497(16) 0.1208(17) 0.076(11) Uani 1 1 d . . . . .
C22 C 0.372(5) 0.4729(14) 0.1523(19) 0.084(12) Uani 1 1 d . . . . .
H22 H 0.265397 0.488785 0.129973 0.101 Uiso 1 1 calc R U . . .
C23 C 0.353(4) 0.4743(15) 0.2128(14) 0.062(9) Uani 1 1 d . . . . .
H23 H 0.240872 0.491079 0.231516 0.074 Uiso 1 1 calc R U . . .
C24 C 0.516(5) 0.4487(15) 0.2459(12) 0.066(10) Uani 1 1 d . . . . .
C25 C 0.332(4) 0.4794(13) 0.3449(12) 0.043(7) Uani 1 1 d . . . . .
C26 C 0.221(4) 0.4528(13) 0.3813(11) 0.041(7) Uani 1 1 d . . . . .
C27 C 0.055(4) 0.4808(10) 0.4057(10) 0.030(6) Uani 1 1 d . . . . .
H27 H -0.027064 0.458729 0.431935 0.036 Uiso 1 1 calc R U . . .
C28 C 0.018(4) 0.5379(15) 0.3914(12) 0.061(10) Uani 1 1 d . . . . .
H28 H -0.099335 0.555782 0.405960 0.073 Uiso 1 1 calc R U . . .
C29 C 0.141(5) 0.5764(14) 0.3551(13) 0.114(17) Uani 1 1 d D . . . .
C30 C 0.083(6) 0.6364(11) 0.3382(14) 0.104(17) Uani 1 1 d D . . . .
H30 H -0.036121 0.652861 0.353386 0.124 Uiso 1 1 calc R U . . .
C31 C 0.192(5) 0.6724(17) 0.3005(18) 0.127(19) Uani 1 1 d D . . . .
C32 C 0.368(7) 0.6460(14) 0.281(2) 0.32(7) Uani 1 1 d D . . . .
H32 H 0.446737 0.668456 0.253472 0.386 Uiso 1 1 calc R U . . .
C33 C 0.429(5) 0.5883(11) 0.2997(16) 0.096(15) Uani 1 1 d D . . . .
H33 H 0.557622 0.574728 0.289838 0.115 Uiso 1 1 calc R U . . .
C34 C 0.310(5) 0.5485(14) 0.3333(13) 0.085(12) Uani 1 1 d D . . . .
B1 B 0.437(5) 0.3740(13) 0.4205(13) 0.035(8) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C21 1.74(4) . ?
Br2 C31 1.84(4) . ?
O1 C16 1.22(5) . ?
O1 B1 1.42(4) . ?
O2 C26 1.37(3) . ?
O2 B1 1.37(4) . ?
N1 C4 1.36(4) . ?
N1 C1 1.40(4) . ?
N1 B1 1.67(4) . ?
N2 C6 1.38(3) . ?
N2 C9 1.44(3) . ?
N2 B1 1.54(3) . ?
C1 C2 1.37(4) . ?
C1 C10 1.52(4) . ?
C2 C3 1.14(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.46(5) . ?
C3 C11 1.51(4) . ?
C4 C5 1.40(4) . ?
C5 C6 1.40(3) . ?
C5 C12 1.54(4) . ?
C6 C7 1.37(4) . ?
C7 C8 1.38(3) . ?
C7 C13 1.56(4) . ?
C8 C9 1.34(3) . ?
C8 H8 0.9500 . ?
C9 C14 1.53(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.36(5) . ?
C15 C25 1.56(4) . ?
C15 C24 1.59(5) . ?
C16 C17 1.56(4) . ?
C17 C18 1.29(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.41(4) . ?
C18 H18 0.9500 . ?
C19 C24 1.39(4) . ?
C19 C20 1.41(4) . ?
C20 C21 1.46(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.42(5) . ?
C22 C23 1.39(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.45(4) . ?
C23 H23 0.9500 . ?
C25 C26 1.27(3) . ?
C25 C34 1.51(4) . ?
C26 C27 1.40(4) . ?
C27 C28 1.29(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.44(4) . ?
C28 H28 0.9500 . ?
C29 C34 1.39(2) . ?
C29 C30 1.40(2) . ?
C30 C31 1.38(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.41(2) . ?
C32 C33 1.38(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.41(2) . ?
C33 H33 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
C16 O1 B1 117(2) . . ?
C26 O2 B1 124(2) . . ?
C4 N1 C1 108(3) . . ?
C4 N1 B1 129(3) . . ?
C1 N1 B1 124(2) . . ?
C6 N2 C9 104(2) . . ?
C6 N2 B1 132(2) . . ?
C9 N2 B1 124(2) . . ?
C2 C1 N1 105(3) . . ?
C2 C1 C10 131(3) . . ?
N1 C1 C10 124(3) . . ?
C3 C2 C1 113(3) . . ?
C3 C2 H2 123.3 . . ?
C1 C2 H2 123.3 . . ?
C2 C3 C4 111(3) . . ?
C2 C3 C11 126(3) . . ?
C4 C3 C11 122(3) . . ?
N1 C4 C5 119(4) . . ?
N1 C4 C3 103(3) . . ?
C5 C4 C3 138(3) . . ?
C4 C5 C6 121(2) . . ?
C4 C5 C12 113(3) . . ?
C6 C5 C12 126(3) . . ?
C7 C6 N2 111(2) . . ?
C7 C6 C5 130(2) . . ?
N2 C6 C5 119(2) . . ?
C6 C7 C8 108(2) . . ?
C6 C7 C13 131(3) . . ?
C8 C7 C13 121(3) . . ?
C9 C8 C7 108(3) . . ?
C9 C8 H8 125.8 . . ?
C7 C8 H8 125.8 . . ?
C8 C9 N2 110(2) . . ?
C8 C9 C14 129(2) . . ?
N2 C9 C14 121(2) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C25 117(3) . . ?
C16 C15 C24 127(4) . . ?
C25 C15 C24 116(3) . . ?
O1 C16 C15 130(3) . . ?
O1 C16 C17 123(3) . . ?
C15 C16 C17 107(4) . . ?
C18 C17 C16 127(3) . . ?
C18 C17 H17 116.4 . . ?
C16 C17 H17 116.4 . . ?
C17 C18 C19 124(3) . . ?
C17 C18 H18 118.2 . . ?
C19 C18 H18 118.2 . . ?
C24 C19 C20 117(3) . . ?
C24 C19 C18 118(3) . . ?
C20 C19 C18 125(3) . . ?
C19 C20 C21 124(3) . . ?
C19 C20 H20 118.2 . . ?
C21 C20 H20 118.2 . . ?
C22 C21 C20 114(3) . . ?
C22 C21 Br1 124(3) . . ?
C20 C21 Br1 122(3) . . ?
C23 C22 C21 126(3) . . ?
C23 C22 H22 117.2 . . ?
C21 C22 H22 117.2 . . ?
C22 C23 C24 116(3) . . ?
C22 C23 H23 121.9 . . ?
C24 C23 H23 121.9 . . ?
C19 C24 C23 123(3) . . ?
C19 C24 C15 116(3) . . ?
C23 C24 C15 121(3) . . ?
C26 C25 C34 120(2) . . ?
C26 C25 C15 123(3) . . ?
C34 C25 C15 117(2) . . ?
C25 C26 O2 119(3) . . ?
C25 C26 C27 124(3) . . ?
O2 C26 C27 118(2) . . ?
C28 C27 C26 118(3) . . ?
C28 C27 H27 121.1 . . ?
C26 C27 H27 121.1 . . ?
C27 C28 C29 125(3) . . ?
C27 C28 H28 117.4 . . ?
C29 C28 H28 117.4 . . ?
C34 C29 C30 122(3) . . ?
C34 C29 C28 116(3) . . ?
C30 C29 C28 121(3) . . ?
C31 C30 C29 122(3) . . ?
C31 C30 H30 118.8 . . ?
C29 C30 H30 118.8 . . ?
C30 C31 C32 116(3) . . ?
C30 C31 Br2 122(2) . . ?
C32 C31 Br2 121(2) . . ?
C33 C32 C31 121(3) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C32 C33 C34 123(3) . . ?
C32 C33 H33 118.6 . . ?
C34 C33 H33 118.6 . . ?
C29 C34 C33 114(3) . . ?
C29 C34 C25 116(2) . . ?
C33 C34 C25 129(2) . . ?
O2 B1 O1 122(2) . . ?
O2 B1 N2 109(2) . . ?
O1 B1 N2 112(2) . . ?
O2 B1 N1 116(2) . . ?
O1 B1 N1 98(2) . . ?
N2 B1 N1 98.6(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 4(3) . . . . ?
B1 N1 C1 C2 178(2) . . . . ?
C4 N1 C1 C10 -177(3) . . . . ?
B1 N1 C1 C10 -2(4) . . . . ?
N1 C1 C2 C3 -3(3) . . . . ?
C10 C1 C2 C3 177(3) . . . . ?
C1 C2 C3 C4 1(4) . . . . ?
C1 C2 C3 C11 -176(2) . . . . ?
C1 N1 C4 C5 -177(2) . . . . ?
B1 N1 C4 C5 9(4) . . . . ?
C1 N1 C4 C3 -3(3) . . . . ?
B1 N1 C4 C3 -177(2) . . . . ?
C2 C3 C4 N1 1(3) . . . . ?
C11 C3 C4 N1 179(2) . . . . ?
C2 C3 C4 C5 173(3) . . . . ?
C11 C3 C4 C5 -9(5) . . . . ?
N1 C4 C5 C6 2(4) . . . . ?
C3 C4 C5 C6 -170(3) . . . . ?
N1 C4 C5 C12 -178(2) . . . . ?
C3 C4 C5 C12 10(5) . . . . ?
C9 N2 C6 C7 3(3) . . . . ?
B1 N2 C6 C7 175(3) . . . . ?
C9 N2 C6 C5 -172(2) . . . . ?
B1 N2 C6 C5 1(4) . . . . ?
C4 C5 C6 C7 179(3) . . . . ?
C12 C5 C6 C7 0(4) . . . . ?
C4 C5 C6 N2 -7(4) . . . . ?
C12 C5 C6 N2 173(3) . . . . ?
N2 C6 C7 C8 -2(3) . . . . ?
C5 C6 C7 C8 172(2) . . . . ?
N2 C6 C7 C13 176(3) . . . . ?
C5 C6 C7 C13 -10(5) . . . . ?
C6 C7 C8 C9 0(3) . . . . ?
C13 C7 C8 C9 -178(2) . . . . ?
C7 C8 C9 N2 1(3) . . . . ?
C7 C8 C9 C14 -175(3) . . . . ?
C6 N2 C9 C8 -3(2) . . . . ?
B1 N2 C9 C8 -176(2) . . . . ?
C6 N2 C9 C14 174(2) . . . . ?
B1 N2 C9 C14 0(4) . . . . ?
B1 O1 C16 C15 47(4) . . . . ?
B1 O1 C16 C17 -128(2) . . . . ?
C25 C15 C16 O1 12(5) . . . . ?
C24 C15 C16 O1 -166(3) . . . . ?
C25 C15 C16 C17 -173(2) . . . . ?
C24 C15 C16 C17 10(4) . . . . ?
O1 C16 C17 C18 174(3) . . . . ?
C15 C16 C17 C18 -2(4) . . . . ?
C16 C17 C18 C19 -7(4) . . . . ?
C17 C18 C19 C24 7(4) . . . . ?
C17 C18 C19 C20 -169(3) . . . . ?
C24 C19 C20 C21 3(4) . . . . ?
C18 C19 C20 C21 178(3) . . . . ?
C19 C20 C21 C22 -2(4) . . . . ?
C19 C20 C21 Br1 -175(2) . . . . ?
C20 C21 C22 C23 1(5) . . . . ?
Br1 C21 C22 C23 174(3) . . . . ?
C21 C22 C23 C24 -1(5) . . . . ?
C20 C19 C24 C23 -3(5) . . . . ?
C18 C19 C24 C23 -179(3) . . . . ?
C20 C19 C24 C15 177(2) . . . . ?
C18 C19 C24 C15 1(4) . . . . ?
C22 C23 C24 C19 2(5) . . . . ?
C22 C23 C24 C15 -178(3) . . . . ?
C16 C15 C24 C19 -11(4) . . . . ?
C25 C15 C24 C19 172(3) . . . . ?
C16 C15 C24 C23 169(3) . . . . ?
C25 C15 C24 C23 -8(4) . . . . ?
C16 C15 C25 C26 -50(4) . . . . ?
C24 C15 C25 C26 127(3) . . . . ?
C16 C15 C25 C34 124(3) . . . . ?
C24 C15 C25 C34 -59(4) . . . . ?
C34 C25 C26 O2 -171(3) . . . . ?
C15 C25 C26 O2 3(4) . . . . ?
C34 C25 C26 C27 10(5) . . . . ?
C15 C25 C26 C27 -176(3) . . . . ?
B1 O2 C26 C25 56(4) . . . . ?
B1 O2 C26 C27 -125(3) . . . . ?
C25 C26 C27 C28 -2(4) . . . . ?
O2 C26 C27 C28 179(2) . . . . ?
C26 C27 C28 C29 -4(4) . . . . ?
C27 C28 C29 C34 1(5) . . . . ?
C27 C28 C29 C30 175(3) . . . . ?
C34 C29 C30 C31 -2(3) . . . . ?
C28 C29 C30 C31 -176(4) . . . . ?
C29 C30 C31 C32 -1(3) . . . . ?
C29 C30 C31 Br2 -172(3) . . . . ?
C30 C31 C32 C33 -2(6) . . . . ?
Br2 C31 C32 C33 169(4) . . . . ?
C31 C32 C33 C34 9(7) . . . . ?
C30 C29 C34 C33 8(5) . . . . ?
C28 C29 C34 C33 -178(3) . . . . ?
C30 C29 C34 C25 -167(3) . . . . ?
C28 C29 C34 C25 6(4) . . . . ?
C32 C33 C34 C29 -12(6) . . . . ?
C32 C33 C34 C25 163(4) . . . . ?
C26 C25 C34 C29 -12(4) . . . . ?
C15 C25 C34 C29 174(3) . . . . ?
C26 C25 C34 C33 173(3) . . . . ?
C15 C25 C34 C33 -2(5) . . . . ?
C26 O2 B1 O1 -34(4) . . . . ?
C26 O2 B1 N2 -166(2) . . . . ?
C26 O2 B1 N1 84(3) . . . . ?
C16 O1 B1 O2 -38(4) . . . . ?
C16 O1 B1 N2 93(3) . . . . ?
C16 O1 B1 N1 -164(2) . . . . ?
C6 N2 B1 O2 -113(3) . . . . ?
C9 N2 B1 O2 58(3) . . . . ?
C6 N2 B1 O1 109(3) . . . . ?
C9 N2 B1 O1 -79(3) . . . . ?
C6 N2 B1 N1 7(3) . . . . ?
C9 N2 B1 N1 179(2) . . . . ?
C4 N1 B1 O2 103(3) . . . . ?
C1 N1 B1 O2 -70(3) . . . . ?
C4 N1 B1 O1 -126(3) . . . . ?
C1 N1 B1 O1 61(3) . . . . ?
C4 N1 B1 N2 -12(4) . . . . ?
C1 N1 B1 N2 175(2) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_R-2phBODIPY
_database_code_depnum_ccdc_archive 'CCDC 1993848'
loop_
_audit_author_name
_audit_author_address
'Yudai Suzuki'
;Keio university
Japan
;
_audit_update_record             
;
2020-03-31 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C46 H35 B Br2 N2 O2'
_chemical_formula_moiety         'C46 H35 B Br2 N2 O2'
_chemical_formula_weight         818.41
_chemical_melting_point          ?
_chemical_absolute_configuration rmad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   14.0582(3)
_cell_length_b                   7.39498(13)
_cell_length_c                   17.5218(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.311(7)
_cell_angle_gamma                90.0000
_cell_volume                     1818.53(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    29705
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832.00
_exptl_absorpt_coefficient_mu    2.279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_T_max  0.934

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            29690
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.672
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             8103
_reflns_number_gt                7652
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_max     0.932
_reflns_Friedel_fraction_full    0.931

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0887
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         8103
_refine_ls_number_parameters     483
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0578P)²+0.0470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         1.04
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 3096 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(4)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.61251(3) 0.62900(6) 0.68606(2) 0.03128(11) Uani 1 1 d . . . . .
Br2 Br 1.13433(2) 0.23049(7) 0.41931(3) 0.04120(14) Uani 1 1 d . . . . .
O1 O 0.63695(15) 0.7001(3) 0.21836(13) 0.0175(5) Uani 1 1 d . . . . .
O2 O 0.60041(15) 0.3745(3) 0.21113(13) 0.0176(5) Uani 1 1 d . . . . .
N1 N 0.48297(19) 0.5782(4) 0.15603(16) 0.0174(6) Uani 1 1 d . . . . .
N2 N 0.64110(18) 0.5643(4) 0.09573(15) 0.0161(5) Uani 1 1 d . . . . .
C1 C 0.4138(2) 0.5880(4) 0.2065(2) 0.0183(7) Uani 1 1 d . . . . .
C2 C 0.3227(2) 0.5955(4) 0.1668(2) 0.0197(7) Uani 1 1 d . . . . .
C3 C 0.3372(2) 0.5860(4) 0.0895(2) 0.0189(7) Uani 1 1 d . . . . .
C4 C 0.4379(2) 0.5722(4) 0.0820(2) 0.0181(7) Uani 1 1 d . . . . .
C5 C 0.4906(2) 0.5544(4) 0.01768(18) 0.0168(6) Uani 1 1 d . . . . .
C6 C 0.5908(2) 0.5605(5) 0.02374(18) 0.0175(6) Uani 1 1 d . . . . .
C7 C 0.6568(2) 0.5831(4) -0.03353(19) 0.0185(7) Uani 1 1 d . . . . .
C8 C 0.7471(2) 0.5987(4) 0.00419(19) 0.0181(7) Uani 1 1 d . . . . .
C9 C 0.7351(2) 0.5851(4) 0.08366(19) 0.0171(7) Uani 1 1 d . . . . .
C10 C 0.4307(2) 0.5865(5) 0.2914(2) 0.0231(7) Uani 1 1 d . . . . .
H10A H 0.448971 0.707972 0.309179 0.028 Uiso 1 1 calc R U . . .
H10B H 0.481974 0.501153 0.305800 0.028 Uiso 1 1 calc R U . . .
H10C H 0.372264 0.549410 0.315029 0.028 Uiso 1 1 calc R U . . .
C11 C 0.2313(2) 0.6134(6) 0.2047(2) 0.0248(7) Uani 1 1 d . . . . .
C12 C 0.2204(3) 0.7417(6) 0.2604(2) 0.0294(8) Uani 1 1 d . . . . .
H12 H 0.272234 0.819576 0.274511 0.035 Uiso 1 1 calc R U . . .
C13 C 0.1352(3) 0.7603(7) 0.2966(2) 0.0369(10) Uani 1 1 d . . . . .
H13 H 0.129587 0.848863 0.335385 0.044 Uiso 1 1 calc R U . . .
C14 C 0.0594(3) 0.6500(7) 0.2759(3) 0.0391(10) Uani 1 1 d . . . . .
H14 H 0.000695 0.663839 0.299656 0.047 Uiso 1 1 calc R U . . .
C15 C 0.0685(3) 0.5196(7) 0.2209(3) 0.0369(10) Uani 1 1 d . . . . .
H15 H 0.016151 0.442997 0.206768 0.044 Uiso 1 1 calc R U . . .
C16 C 0.1549(3) 0.4991(6) 0.1854(3) 0.0302(8) Uani 1 1 d . . . . .
H16 H 0.161282 0.407217 0.148114 0.036 Uiso 1 1 calc R U . . .
C17 C 0.2602(2) 0.6034(5) 0.0264(2) 0.0234(7) Uani 1 1 d . . . . .
H17A H 0.279252 0.693691 -0.010748 0.028 Uiso 1 1 calc R U . . .
H17B H 0.200714 0.641537 0.048063 0.028 Uiso 1 1 calc R U . . .
H17C H 0.250671 0.486431 0.000825 0.028 Uiso 1 1 calc R U . . .
C18 C 0.4408(2) 0.5266(5) -0.0594(2) 0.0220(7) Uani 1 1 d . . . . .
H18A H 0.426644 0.644281 -0.083181 0.026 Uiso 1 1 calc R U . . .
H18B H 0.381217 0.460453 -0.053684 0.026 Uiso 1 1 calc R U . . .
H18C H 0.481923 0.456877 -0.091830 0.026 Uiso 1 1 calc R U . . .
C19 C 0.6371(3) 0.6058(5) -0.11842(18) 0.0234(7) Uani 1 1 d . . . . .
H19A H 0.693222 0.658088 -0.140811 0.028 Uiso 1 1 calc R U . . .
H19B H 0.582442 0.686521 -0.127938 0.028 Uiso 1 1 calc R U . . .
H19C H 0.622990 0.487692 -0.141722 0.028 Uiso 1 1 calc R U . . .
C20 C 0.8386(2) 0.6204(6) -0.03190(18) 0.0220(7) Uani 1 1 d . . . . .
C21 C 0.8581(3) 0.5177(5) -0.0966(2) 0.0278(8) Uani 1 1 d . . . . .
H21 H 0.811281 0.436489 -0.117654 0.033 Uiso 1 1 calc R U . . .
C22 C 0.9452(3) 0.5332(6) -0.1303(2) 0.0344(9) Uani 1 1 d . . . . .
H22 H 0.957506 0.462340 -0.173875 0.041 Uiso 1 1 calc R U . . .
C23 C 1.0136(3) 0.6521(7) -0.1001(2) 0.0347(9) Uani 1 1 d . . . . .
H23 H 1.073204 0.661971 -0.122742 0.042 Uiso 1 1 calc R U . . .
C24 C 0.9952(3) 0.7567(6) -0.0370(2) 0.0303(8) Uani 1 1 d . . . . .
H24 H 1.041765 0.839576 -0.016817 0.036 Uiso 1 1 calc R U . . .
C25 C 0.9084(2) 0.7401(5) -0.0031(2) 0.0248(7) Uani 1 1 d . . . . .
H25 H 0.896526 0.811587 0.040422 0.030 Uiso 1 1 calc R U . . .
C26 C 0.8125(2) 0.5890(5) 0.14538(19) 0.0232(8) Uani 1 1 d . . . . .
H26A H 0.874484 0.586720 0.122566 0.028 Uiso 1 1 calc R U . . .
H26B H 0.806762 0.483221 0.178516 0.028 Uiso 1 1 calc R U . . .
H26C H 0.807095 0.699523 0.175672 0.028 Uiso 1 1 calc R U . . .
C27 C 0.6392(2) 0.7092(5) 0.29612(18) 0.0178(6) Uani 1 1 d . . . . .
C28 C 0.6074(2) 0.8742(5) 0.3274(2) 0.0212(7) Uani 1 1 d . . . . .
H28 H 0.590308 0.972523 0.294522 0.025 Uiso 1 1 calc R U . . .
C29 C 0.6013(3) 0.8920(5) 0.4046(2) 0.0227(7) Uani 1 1 d . . . . .
H29 H 0.582958 1.004646 0.425248 0.027 Uiso 1 1 calc R U . . .
C30 C 0.6220(2) 0.7446(5) 0.45396(19) 0.0217(7) Uani 1 1 d . . . . .
C31 C 0.6081(2) 0.7557(5) 0.5333(2) 0.0236(7) Uani 1 1 d . . . . .
H31 H 0.585385 0.864607 0.554503 0.028 Uiso 1 1 calc R U . . .
C32 C 0.6276(2) 0.6097(6) 0.57911(18) 0.0241(7) Uani 1 1 d . . . . .
C33 C 0.6578(2) 0.4439(5) 0.5494(2) 0.0229(7) Uani 1 1 d . . . . .
H33 H 0.667776 0.341972 0.581891 0.028 Uiso 1 1 calc R U . . .
C34 C 0.6725(2) 0.4315(5) 0.4732(2) 0.0219(7) Uani 1 1 d . . . . .
H34 H 0.693806 0.320068 0.453229 0.026 Uiso 1 1 calc R U . . .
C35 C 0.6569(2) 0.5810(5) 0.42300(19) 0.0183(7) Uani 1 1 d . . . . .
C36 C 0.6724(2) 0.5707(5) 0.34246(19) 0.0193(7) Uani 1 1 d . . . . .
C37 C 0.6840(2) 0.3207(5) 0.24725(19) 0.0181(6) Uani 1 1 d . . . . .
C38 C 0.7288(2) 0.1648(5) 0.2198(2) 0.0219(7) Uani 1 1 d . . . . .
H38 H 0.698599 0.097338 0.179117 0.026 Uiso 1 1 calc R U . . .
C39 C 0.8150(3) 0.1104(6) 0.2511(2) 0.0255(7) Uani 1 1 d . . . . .
H39 H 0.843277 0.003156 0.233021 0.031 Uiso 1 1 calc R U . . .
C40 C 0.8628(2) 0.2108(6) 0.3099(2) 0.0235(7) Uani 1 1 d . . . . .
C41 C 0.9583(3) 0.1684(6) 0.3365(2) 0.0299(9) Uani 1 1 d . . . . .
H41 H 0.989582 0.066230 0.316626 0.036 Uiso 1 1 calc R U . . .
C42 C 1.0043(2) 0.2742(6) 0.3900(2) 0.0311(9) Uani 1 1 d . . . . .
C43 C 0.9598(3) 0.4236(6) 0.4220(2) 0.0304(8) Uani 1 1 d . . . . .
H43 H 0.992821 0.493965 0.460372 0.036 Uiso 1 1 calc R U . . .
C44 C 0.8680(2) 0.4676(6) 0.3974(2) 0.0256(8) Uani 1 1 d . . . . .
H44 H 0.838388 0.569766 0.418816 0.031 Uiso 1 1 calc R U . . .
C45 C 0.8166(2) 0.3637(5) 0.34071(19) 0.0202(7) Uani 1 1 d . . . . .
C46 C 0.7224(2) 0.4135(5) 0.31085(18) 0.0182(6) Uani 1 1 d . . . . .
B1 B 0.5934(2) 0.5524(5) 0.1743(2) 0.0168(7) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C32 1.903(3) . ?
Br2 C42 1.898(3) . ?
O1 C27 1.363(4) . ?
O1 B1 1.453(4) . ?
O2 C37 1.361(4) . ?
O2 B1 1.466(5) . ?
N1 C1 1.354(4) . ?
N1 C4 1.412(4) . ?
N1 B1 1.578(4) . ?
N2 C9 1.358(4) . ?
N2 C6 1.410(4) . ?
N2 B1 1.568(4) . ?
C1 C2 1.423(4) . ?
C1 C10 1.493(5) . ?
C2 C3 1.383(5) . ?
C2 C11 1.487(5) . ?
C3 C4 1.433(4) . ?
C3 C17 1.507(4) . ?
C4 C5 1.390(5) . ?
C5 C6 1.407(4) . ?
C5 C18 1.500(4) . ?
C6 C7 1.415(5) . ?
C7 C8 1.401(4) . ?
C7 C19 1.506(4) . ?
C8 C9 1.416(4) . ?
C8 C20 1.475(4) . ?
C9 C26 1.490(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.376(6) . ?
C11 C16 1.393(5) . ?
C12 C13 1.395(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.374(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.404(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C25 1.394(5) . ?
C20 C21 1.404(5) . ?
C21 C22 1.394(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.387(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C36 1.372(5) . ?
C27 C28 1.420(5) . ?
C28 C29 1.367(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.411(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.417(5) . ?
C30 C35 1.424(5) . ?
C31 C32 1.364(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.407(6) . ?
C33 C34 1.366(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.422(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.442(5) . ?
C36 C46 1.482(5) . ?
C37 C46 1.391(5) . ?
C37 C38 1.412(5) . ?
C38 C39 1.361(5) . ?
C38 H38 0.9500 . ?
C39 C40 1.408(5) . ?
C39 H39 0.9500 . ?
C40 C45 1.426(5) . ?
C40 C41 1.431(5) . ?
C41 C42 1.356(6) . ?
C41 H41 0.9500 . ?
C42 C43 1.403(6) . ?
C43 C44 1.375(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.421(5) . ?
C44 H44 0.9500 . ?
C45 C46 1.443(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
C27 O1 B1 123.6(3) . . ?
C37 O2 B1 120.1(3) . . ?
C1 N1 C4 107.5(3) . . ?
C1 N1 B1 127.5(3) . . ?
C4 N1 B1 124.5(3) . . ?
C9 N2 C6 107.7(3) . . ?
C9 N2 B1 127.7(3) . . ?
C6 N2 B1 124.5(3) . . ?
N1 C1 C2 110.0(3) . . ?
N1 C1 C10 124.9(3) . . ?
C2 C1 C10 125.1(3) . . ?
C3 C2 C1 107.3(3) . . ?
C3 C2 C11 128.5(3) . . ?
C1 C2 C11 124.1(3) . . ?
C2 C3 C4 107.2(3) . . ?
C2 C3 C17 125.0(3) . . ?
C4 C3 C17 127.6(3) . . ?
C5 C4 N1 121.0(3) . . ?
C5 C4 C3 131.1(3) . . ?
N1 C4 C3 107.9(3) . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 C18 120.0(3) . . ?
C6 C5 C18 119.1(3) . . ?
C5 C6 N2 121.1(3) . . ?
C5 C6 C7 130.1(3) . . ?
N2 C6 C7 108.4(3) . . ?
C8 C7 C6 106.8(3) . . ?
C8 C7 C19 124.5(3) . . ?
C6 C7 C19 128.5(3) . . ?
C7 C8 C9 107.6(3) . . ?
C7 C8 C20 126.5(3) . . ?
C9 C8 C20 125.9(3) . . ?
N2 C9 C8 109.5(3) . . ?
N2 C9 C26 124.4(3) . . ?
C8 C9 C26 126.1(3) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.4(3) . . ?
C12 C11 C2 120.8(3) . . ?
C16 C11 C2 120.7(4) . . ?
C11 C12 C13 121.6(4) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 119.7(4) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 119.9(4) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 120.3(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.1(4) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C3 C17 H17A 109.5 . . ?
C3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C19 H19A 109.5 . . ?
C7 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C7 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 118.0(3) . . ?
C25 C20 C8 121.8(3) . . ?
C21 C20 C8 120.2(3) . . ?
C22 C21 C20 121.0(4) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C23 C22 C21 119.8(4) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 120.0(4) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 121.1(4) . . ?
C24 C25 H25 119.4 . . ?
C20 C25 H25 119.4 . . ?
C9 C26 H26A 109.5 . . ?
C9 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C9 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O1 C27 C36 122.9(3) . . ?
O1 C27 C28 116.0(3) . . ?
C36 C27 C28 121.1(3) . . ?
C29 C28 C27 120.2(3) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 120.6(3) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C29 C30 C31 121.4(3) . . ?
C29 C30 C35 119.1(3) . . ?
C31 C30 C35 119.5(3) . . ?
C32 C31 C30 119.8(3) . . ?
C32 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C31 C32 C33 121.8(3) . . ?
C31 C32 Br1 119.3(3) . . ?
C33 C32 Br1 118.9(3) . . ?
C34 C33 C32 119.1(3) . . ?
C34 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
C33 C34 C35 121.7(3) . . ?
C33 C34 H34 119.2 . . ?
C35 C34 H34 119.2 . . ?
C34 C35 C30 118.0(3) . . ?
C34 C35 C36 122.5(3) . . ?
C30 C35 C36 119.5(3) . . ?
C27 C36 C35 118.3(3) . . ?
C27 C36 C46 121.1(3) . . ?
C35 C36 C46 120.6(3) . . ?
O2 C37 C46 120.9(3) . . ?
O2 C37 C38 118.1(3) . . ?
C46 C37 C38 121.0(3) . . ?
C39 C38 C37 120.6(3) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C38 C39 C40 121.0(4) . . ?
C38 C39 H39 119.5 . . ?
C40 C39 H39 119.5 . . ?
C39 C40 C45 119.1(3) . . ?
C39 C40 C41 121.5(3) . . ?
C45 C40 C41 119.3(3) . . ?
C42 C41 C40 120.0(4) . . ?
C42 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
C41 C42 C43 121.7(3) . . ?
C41 C42 Br2 120.1(3) . . ?
C43 C42 Br2 118.1(3) . . ?
C44 C43 C42 119.5(4) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C43 C44 C45 121.4(4) . . ?
C43 C44 H44 119.3 . . ?
C45 C44 H44 119.3 . . ?
C44 C45 C40 118.0(3) . . ?
C44 C45 C46 122.3(3) . . ?
C40 C45 C46 119.6(3) . . ?
C37 C46 C45 118.0(3) . . ?
C37 C46 C36 121.1(3) . . ?
C45 C46 C36 120.6(3) . . ?
O1 B1 O2 115.2(3) . . ?
O1 B1 N2 103.6(3) . . ?
O2 B1 N2 114.5(3) . . ?
O1 B1 N1 113.4(3) . . ?
O2 B1 N1 103.8(3) . . ?
N2 B1 N1 106.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -2.2(4) . . . . ?
B1 N1 C1 C2 -174.8(3) . . . . ?
C4 N1 C1 C10 176.4(3) . . . . ?
B1 N1 C1 C10 3.8(5) . . . . ?
N1 C1 C2 C3 1.3(4) . . . . ?
C10 C1 C2 C3 -177.3(3) . . . . ?
N1 C1 C2 C11 -177.8(3) . . . . ?
C10 C1 C2 C11 3.6(5) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C11 C2 C3 C4 179.2(3) . . . . ?
C1 C2 C3 C17 -175.2(3) . . . . ?
C11 C2 C3 C17 3.9(6) . . . . ?
C1 N1 C4 C5 -177.4(3) . . . . ?
B1 N1 C4 C5 -4.5(5) . . . . ?
C1 N1 C4 C3 2.2(4) . . . . ?
B1 N1 C4 C3 175.2(3) . . . . ?
C2 C3 C4 C5 178.1(4) . . . . ?
C17 C3 C4 C5 -6.7(6) . . . . ?
C2 C3 C4 N1 -1.4(4) . . . . ?
C17 C3 C4 N1 173.7(3) . . . . ?
N1 C4 C5 C6 -6.6(5) . . . . ?
C3 C4 C5 C6 173.9(3) . . . . ?
N1 C4 C5 C18 172.8(3) . . . . ?
C3 C4 C5 C18 -6.7(5) . . . . ?
C4 C5 C6 N2 7.2(5) . . . . ?
C18 C5 C6 N2 -172.2(3) . . . . ?
C4 C5 C6 C7 -165.2(3) . . . . ?
C18 C5 C6 C7 15.3(5) . . . . ?
C9 N2 C6 C5 -175.0(3) . . . . ?
B1 N2 C6 C5 3.2(5) . . . . ?
C9 N2 C6 C7 -1.1(4) . . . . ?
B1 N2 C6 C7 177.2(3) . . . . ?
C5 C6 C7 C8 173.8(3) . . . . ?
N2 C6 C7 C8 0.6(4) . . . . ?
C5 C6 C7 C19 -0.6(6) . . . . ?
N2 C6 C7 C19 -173.7(3) . . . . ?
C6 C7 C8 C9 0.1(4) . . . . ?
C19 C7 C8 C9 174.7(3) . . . . ?
C6 C7 C8 C20 178.6(3) . . . . ?
C19 C7 C8 C20 -6.8(5) . . . . ?
C6 N2 C9 C8 1.2(3) . . . . ?
B1 N2 C9 C8 -177.0(3) . . . . ?
C6 N2 C9 C26 -177.8(3) . . . . ?
B1 N2 C9 C26 4.1(5) . . . . ?
C7 C8 C9 N2 -0.8(4) . . . . ?
C20 C8 C9 N2 -179.3(3) . . . . ?
C7 C8 C9 C26 178.1(3) . . . . ?
C20 C8 C9 C26 -0.4(5) . . . . ?
C3 C2 C11 C12 -130.8(4) . . . . ?
C1 C2 C11 C12 48.1(5) . . . . ?
C3 C2 C11 C16 50.0(5) . . . . ?
C1 C2 C11 C16 -131.1(4) . . . . ?
C16 C11 C12 C13 -0.7(6) . . . . ?
C2 C11 C12 C13 -180.0(4) . . . . ?
C11 C12 C13 C14 -0.9(7) . . . . ?
C12 C13 C14 C15 1.3(7) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
C12 C11 C16 C15 1.7(6) . . . . ?
C2 C11 C16 C15 -179.0(4) . . . . ?
C14 C15 C16 C11 -1.3(6) . . . . ?
C7 C8 C20 C25 138.1(4) . . . . ?
C9 C8 C20 C25 -43.7(5) . . . . ?
C7 C8 C20 C21 -42.6(5) . . . . ?
C9 C8 C20 C21 135.6(4) . . . . ?
C25 C20 C21 C22 0.9(6) . . . . ?
C8 C20 C21 C22 -178.4(4) . . . . ?
C20 C21 C22 C23 -0.4(6) . . . . ?
C21 C22 C23 C24 -0.6(7) . . . . ?
C22 C23 C24 C25 1.0(6) . . . . ?
C23 C24 C25 C20 -0.5(6) . . . . ?
C21 C20 C25 C24 -0.5(6) . . . . ?
C8 C20 C25 C24 178.8(3) . . . . ?
B1 O1 C27 C36 52.3(4) . . . . ?
B1 O1 C27 C28 -129.5(3) . . . . ?
O1 C27 C28 C29 175.8(3) . . . . ?
C36 C27 C28 C29 -5.9(5) . . . . ?
C27 C28 C29 C30 -3.1(5) . . . . ?
C28 C29 C30 C31 -174.5(3) . . . . ?
C28 C29 C30 C35 5.1(5) . . . . ?
C29 C30 C31 C32 179.0(3) . . . . ?
C35 C30 C31 C32 -0.5(5) . . . . ?
C30 C31 C32 C33 -2.5(5) . . . . ?
C30 C31 C32 Br1 178.0(2) . . . . ?
C31 C32 C33 C34 3.3(5) . . . . ?
Br1 C32 C33 C34 -177.3(3) . . . . ?
C32 C33 C34 C35 -0.9(5) . . . . ?
C33 C34 C35 C30 -2.1(5) . . . . ?
C33 C34 C35 C36 179.8(3) . . . . ?
C29 C30 C35 C34 -176.8(3) . . . . ?
C31 C30 C35 C34 2.8(5) . . . . ?
C29 C30 C35 C36 1.4(5) . . . . ?
C31 C30 C35 C36 -179.0(3) . . . . ?
O1 C27 C36 C35 -169.6(3) . . . . ?
C28 C27 C36 C35 12.2(5) . . . . ?
O1 C27 C36 C46 9.9(5) . . . . ?
C28 C27 C36 C46 -168.2(3) . . . . ?
C34 C35 C36 C27 168.2(3) . . . . ?
C30 C35 C36 C27 -10.0(5) . . . . ?
C34 C35 C36 C46 -11.4(5) . . . . ?
C30 C35 C36 C46 170.5(3) . . . . ?
B1 O2 C37 C46 63.3(4) . . . . ?
B1 O2 C37 C38 -118.7(3) . . . . ?
O2 C37 C38 C39 176.5(3) . . . . ?
C46 C37 C38 C39 -5.5(5) . . . . ?
C37 C38 C39 C40 -1.9(5) . . . . ?
C38 C39 C40 C45 4.8(6) . . . . ?
C38 C39 C40 C41 -171.9(4) . . . . ?
C39 C40 C41 C42 176.1(4) . . . . ?
C45 C40 C41 C42 -0.5(6) . . . . ?
C40 C41 C42 C43 1.5(6) . . . . ?
C40 C41 C42 Br2 -174.8(3) . . . . ?
C41 C42 C43 C44 -1.6(6) . . . . ?
Br2 C42 C43 C44 174.8(3) . . . . ?
C42 C43 C44 C45 0.7(6) . . . . ?
C43 C44 C45 C40 0.2(6) . . . . ?
C43 C44 C45 C46 -176.2(4) . . . . ?
C39 C40 C45 C44 -177.1(3) . . . . ?
C41 C40 C45 C44 -0.3(5) . . . . ?
C39 C40 C45 C46 -0.5(5) . . . . ?
C41 C40 C45 C46 176.3(3) . . . . ?
O2 C37 C46 C45 -172.5(3) . . . . ?
C38 C37 C46 C45 9.6(5) . . . . ?
O2 C37 C46 C36 1.6(5) . . . . ?
C38 C37 C46 C36 -176.3(3) . . . . ?
C44 C45 C46 C37 169.9(3) . . . . ?
C40 C45 C46 C37 -6.5(5) . . . . ?
C44 C45 C46 C36 -4.2(5) . . . . ?
C40 C45 C46 C36 179.4(3) . . . . ?
C27 C36 C46 C37 -49.6(5) . . . . ?
C35 C36 C46 C37 130.0(3) . . . . ?
C27 C36 C46 C45 124.4(4) . . . . ?
C35 C36 C46 C45 -56.1(4) . . . . ?
C27 O1 B1 O2 -33.6(4) . . . . ?
C27 O1 B1 N2 -159.5(3) . . . . ?
C27 O1 B1 N1 85.7(3) . . . . ?
C37 O2 B1 O1 -43.7(4) . . . . ?
C37 O2 B1 N2 76.4(4) . . . . ?
C37 O2 B1 N1 -168.1(3) . . . . ?
C9 N2 B1 O1 46.3(4) . . . . ?
C6 N2 B1 O1 -131.5(3) . . . . ?
C9 N2 B1 O2 -79.9(4) . . . . ?
C6 N2 B1 O2 102.2(3) . . . . ?
C9 N2 B1 N1 166.1(3) . . . . ?
C6 N2 B1 N1 -11.8(4) . . . . ?
C1 N1 B1 O1 -62.9(4) . . . . ?
C4 N1 B1 O1 125.6(3) . . . . ?
C1 N1 B1 O2 62.8(4) . . . . ?
C4 N1 B1 O2 -108.7(3) . . . . ?
C1 N1 B1 N2 -176.1(3) . . . . ?
C4 N1 B1 N2 12.5(4) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_R-1PhBODIPY
_database_code_depnum_ccdc_archive 'CCDC 1993847'
loop_
_audit_author_name
_audit_author_address
'Yudai Suzuki'
;Keio university
Japan
;
_audit_update_record             
;
2020-03-31 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C46 H45 B Br2 N2 O2'
_chemical_formula_moiety         'C40 H31 B Br2 N2 O2, C6 H14'
_chemical_formula_weight         828.49
_chemical_melting_point          ?
_chemical_absolute_configuration rmad

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.7759(3)
_cell_length_b                   22.5581(11)
_cell_length_c                   26.3420(13)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     4026.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22927
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      25.31
_cell_measurement_temperature    103
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1704.00
_exptl_absorpt_coefficient_mu    2.059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.399
_exptl_absorpt_correction_T_max  0.960

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      103
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            55815
_diffrn_reflns_av_unetI/netI     0.1192
_diffrn_reflns_av_R_equivalents  0.2114
_diffrn_reflns_theta_max         25.334
_diffrn_reflns_theta_min         2.817
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             7345
_reflns_number_gt                4365
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1429
_refine_ls_R_factor_gt           0.0797
_refine_ls_wR_factor_ref         0.1903
_refine_ls_wR_factor_gt          0.1649
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         7345
_refine_ls_number_parameters     485
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0930P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.17
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1193 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.076(8)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
B B 0.0013 0.0007
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.0343(4) 0.73829(8) 0.04577(6) 0.1124(9) Uani 1 1 d . . . . .
Br2 Br 0.26874(18) 0.39093(5) 0.23082(6) 0.0659(5) Uani 1 1 d . . . . .
O1 O -0.0075(10) 0.7147(3) 0.3568(2) 0.0333(17) Uani 1 1 d . . . . .
O2 O 0.3560(9) 0.7215(3) 0.3540(3) 0.0307(17) Uani 1 1 d . . . . .
N1 N 0.1846(11) 0.7958(4) 0.4010(3) 0.029(2) Uani 1 1 d . . . . .
N2 N 0.1693(12) 0.6907(4) 0.4330(3) 0.034(2) Uani 1 1 d . . . . .
C1 C 0.2004(14) 0.8438(4) 0.3711(4) 0.034(3) Uani 1 1 d . . . . .
C2 C 0.1997(13) 0.8957(5) 0.4018(4) 0.035(3) Uani 1 1 d . . . . .
C3 C 0.1825(13) 0.8783(4) 0.4515(4) 0.031(2) Uani 1 1 d . . . . .
C4 C 0.1754(13) 0.8151(4) 0.4515(4) 0.029(2) Uani 1 1 d . . . . .
C5 C 0.1728(14) 0.7746(5) 0.4909(4) 0.035(3) Uani 1 1 d . . . . .
C6 C 0.1802(14) 0.7135(5) 0.4828(4) 0.037(3) Uani 1 1 d . . . . .
C7 C 0.1778(13) 0.6638(5) 0.5173(4) 0.034(3) Uani 1 1 d . . . . .
C8 C 0.1625(14) 0.6158(5) 0.4885(4) 0.035(3) Uani 1 1 d . . . . .
H8 H 0.160670 0.576233 0.500959 0.042 Uiso 1 1 calc R U . . .
C9 C 0.1494(13) 0.6314(4) 0.4378(4) 0.031(3) Uani 1 1 d . . . . .
C10 C 0.2226(17) 0.8419(4) 0.3153(4) 0.037(3) Uani 1 1 d . . . . .
H10A H 0.107846 0.822073 0.300298 0.045 Uiso 1 1 calc R U . . .
H10B H 0.342681 0.819992 0.306520 0.045 Uiso 1 1 calc R U . . .
H10C H 0.231824 0.882420 0.302080 0.045 Uiso 1 1 calc R U . . .
C11 C 0.217(2) 0.9582(5) 0.3838(4) 0.046(3) Uani 1 1 d . . . . .
C12 C 0.382(2) 0.9779(5) 0.3577(4) 0.054(3) Uani 1 1 d . . . . .
H12 H 0.479877 0.950392 0.347011 0.065 Uiso 1 1 calc R U . . .
C13 C 0.405(3) 1.0385(6) 0.3471(5) 0.069(4) Uani 1 1 d . . . . .
H13 H 0.522526 1.051491 0.330892 0.083 Uiso 1 1 calc R U . . .
C14 C 0.270(3) 1.0777(6) 0.3587(5) 0.071(4) Uani 1 1 d . . . . .
H14 H 0.287343 1.118260 0.349960 0.086 Uiso 1 1 calc R U . . .
C15 C 0.099(3) 1.0589(6) 0.3843(5) 0.074(5) Uani 1 1 d . . . . .
H15 H -0.000033 1.087008 0.392757 0.089 Uiso 1 1 calc R U . . .
C16 C 0.072(2) 1.0001(5) 0.3973(5) 0.062(4) Uani 1 1 d . . . . .
H16 H -0.042271 0.988050 0.415286 0.075 Uiso 1 1 calc R U . . .
C17 C 0.1813(15) 0.9208(5) 0.4960(4) 0.039(3) Uani 1 1 d . . . . .
H17A H 0.281936 0.908820 0.520628 0.047 Uiso 1 1 calc R U . . .
H17B H 0.051177 0.920266 0.512179 0.047 Uiso 1 1 calc R U . . .
H17C H 0.210111 0.960988 0.483835 0.047 Uiso 1 1 calc R U . . .
C18 C 0.1584(14) 0.7972(5) 0.5455(4) 0.036(3) Uani 1 1 d . . . . .
H18A H 0.072670 0.832130 0.546633 0.043 Uiso 1 1 calc R U . . .
H18B H 0.290272 0.807819 0.557784 0.043 Uiso 1 1 calc R U . . .
H18C H 0.103034 0.765996 0.567186 0.043 Uiso 1 1 calc R U . . .
C19 C 0.1940(16) 0.6638(5) 0.5739(4) 0.044(3) Uani 1 1 d . . . . .
H19A H 0.305121 0.688889 0.584201 0.053 Uiso 1 1 calc R U . . .
H19B H 0.215745 0.623251 0.585895 0.053 Uiso 1 1 calc R U . . .
H19C H 0.071703 0.679383 0.588620 0.053 Uiso 1 1 calc R U . . .
C20 C 0.1116(16) 0.5888(4) 0.3955(4) 0.037(3) Uani 1 1 d . . . . .
H20A H 0.026564 0.607605 0.370054 0.044 Uiso 1 1 calc R U . . .
H20B H 0.046133 0.553366 0.408889 0.044 Uiso 1 1 calc R U . . .
H20C H 0.237131 0.577539 0.379759 0.044 Uiso 1 1 calc R U . . .
C21 C -0.0346(15) 0.7179(4) 0.3073(4) 0.032(2) Uani 1 1 d . . . . .
C22 C -0.2112(16) 0.7454(4) 0.2901(4) 0.036(3) Uani 1 1 d . . . . .
H22 H -0.303618 0.760032 0.314110 0.043 Uiso 1 1 calc R U . . .
C23 C -0.250(2) 0.7512(4) 0.2389(5) 0.050(3) Uani 1 1 d . . . . .
H23 H -0.371822 0.767803 0.227842 0.060 Uiso 1 1 calc R U . . .
C24 C -0.108(2) 0.7324(5) 0.2027(4) 0.049(3) Uani 1 1 d . . . . .
C25 C -0.134(2) 0.7425(5) 0.1492(5) 0.063(4) Uani 1 1 d . . . . .
H25 H -0.250435 0.761086 0.137158 0.076 Uiso 1 1 calc R U . . .
C26 C 0.006(3) 0.7258(5) 0.1163(5) 0.065(4) Uani 1 1 d . . . . .
C27 C 0.178(2) 0.6982(6) 0.1313(5) 0.063(4) Uani 1 1 d . . . . .
H27 H 0.273867 0.687131 0.106895 0.076 Uiso 1 1 calc R U . . .
C28 C 0.209(2) 0.6868(4) 0.1828(4) 0.047(3) Uani 1 1 d . . . . .
H28 H 0.328611 0.668385 0.193319 0.056 Uiso 1 1 calc R U . . .
C29 C 0.0633(17) 0.7028(5) 0.2199(4) 0.043(3) Uani 1 1 d . . . . .
C30 C 0.0918(14) 0.6928(4) 0.2727(4) 0.033(2) Uani 1 1 d . . . . .
C31 C 0.3835(15) 0.6701(4) 0.3287(4) 0.031(2) Uani 1 1 d . . . . .
C32 C 0.5464(14) 0.6350(4) 0.3403(4) 0.030(2) Uani 1 1 d . . . . .
H32 H 0.642563 0.649898 0.363194 0.036 Uiso 1 1 calc R U . . .
C33 C 0.5729(16) 0.5797(5) 0.3198(4) 0.039(3) Uani 1 1 d . . . . .
H33 H 0.689216 0.557814 0.327071 0.046 Uiso 1 1 calc R U . . .
C34 C 0.4267(15) 0.5556(5) 0.2879(4) 0.038(3) Uani 1 1 d . . . . .
C35 C 0.4246(17) 0.4952(4) 0.2727(4) 0.042(3) Uani 1 1 d . . . . .
H35 H 0.531477 0.470031 0.281588 0.050 Uiso 1 1 calc R U . . .
C36 C 0.2748(17) 0.4737(5) 0.2461(5) 0.048(3) Uani 1 1 d . . . . .
C37 C 0.1137(18) 0.5075(5) 0.2306(5) 0.049(3) Uani 1 1 d . . . . .
H37 H 0.008119 0.489993 0.212236 0.059 Uiso 1 1 calc R U . . .
C38 C 0.1113(17) 0.5672(5) 0.2426(4) 0.045(3) Uani 1 1 d . . . . .
H38 H 0.006130 0.591309 0.230751 0.055 Uiso 1 1 calc R U . . .
C39 C 0.2626(15) 0.5928(4) 0.2723(4) 0.035(2) Uani 1 1 d . . . . .
C40 C 0.2542(16) 0.6532(4) 0.2902(4) 0.036(3) Uani 1 1 d . . . . .
C41 C 0.166(4) 0.8815(13) 0.1621(10) 0.185(14) Uani 1 1 d D . . . .
H41A H 0.134159 0.923352 0.156640 0.222 Uiso 1 1 calc R U . . .
H41B H 0.176363 0.873700 0.198653 0.222 Uiso 1 1 calc R U . . .
H41C H 0.062216 0.856626 0.147517 0.222 Uiso 1 1 calc R U . . .
C42 C 0.363(4) 0.8671(10) 0.1367(10) 0.180(14) Uani 1 1 d D . . . .
H42A H 0.357554 0.825772 0.124163 0.216 Uiso 1 1 calc R U . . .
H42B H 0.468161 0.869246 0.162595 0.216 Uiso 1 1 calc R U . . .
C43 C 0.420(4) 0.9080(9) 0.0918(9) 0.144(9) Uani 1 1 d . . . . .
H43A H 0.314851 0.905076 0.065927 0.172 Uiso 1 1 calc R U . . .
H43B H 0.420500 0.949290 0.104431 0.172 Uiso 1 1 calc R U . . .
C44 C 0.619(4) 0.8971(13) 0.0648(11) 0.167(10) Uani 1 1 d . . . . .
H44A H 0.726162 0.898448 0.090452 0.200 Uiso 1 1 calc R U . . .
H44B H 0.618195 0.856718 0.050082 0.200 Uiso 1 1 calc R U . . .
C45 C 0.664(3) 0.9384(10) 0.0256(8) 0.127(8) Uani 1 1 d D . . . .
H45A H 0.679673 0.978212 0.040910 0.153 Uiso 1 1 calc R U . . .
H45B H 0.550933 0.940222 0.001863 0.153 Uiso 1 1 calc R U . . .
C46 C 0.853(3) 0.9235(9) -0.0050(9) 0.136(8) Uani 1 1 d D . . . .
H46A H 0.877079 0.954724 -0.030129 0.163 Uiso 1 1 calc R U . . .
H46B H 0.835538 0.885476 -0.022383 0.163 Uiso 1 1 calc R U . . .
H46C H 0.965790 0.920952 0.018179 0.163 Uiso 1 1 calc R U . . .
B1 B 0.1759(16) 0.7301(5) 0.3826(4) 0.028(3) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C26 1.898(13) . ?
Br2 C36 1.910(10) . ?
O1 C21 1.317(11) . ?
O1 B1 1.459(13) . ?
O2 C31 1.351(11) . ?
O2 B1 1.447(13) . ?
N1 C1 1.343(13) . ?
N1 C4 1.400(13) . ?
N1 B1 1.560(14) . ?
N2 C9 1.350(12) . ?
N2 C6 1.412(13) . ?
N2 B1 1.598(14) . ?
C1 C2 1.425(14) . ?
C1 C10 1.477(14) . ?
C2 C3 1.372(14) . ?
C2 C11 1.494(15) . ?
C3 C4 1.426(13) . ?
C3 C17 1.514(14) . ?
C4 C5 1.383(14) . ?
C5 C6 1.396(15) . ?
C5 C18 1.529(14) . ?
C6 C7 1.441(15) . ?
C7 C8 1.327(15) . ?
C7 C19 1.495(15) . ?
C8 C9 1.384(14) . ?
C8 H8 0.9500 . ?
C9 C20 1.494(14) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.385(17) . ?
C11 C16 1.407(17) . ?
C12 C13 1.404(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.31(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.41(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C30 1.374(14) . ?
C21 C22 1.423(14) . ?
C22 C23 1.381(15) . ?
C22 H22 0.9500 . ?
C23 C24 1.421(17) . ?
C23 H23 0.9500 . ?
C24 C29 1.412(16) . ?
C24 C25 1.439(16) . ?
C25 C26 1.336(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.38(2) . ?
C27 C28 1.395(16) . ?
C27 H27 0.9500 . ?
C28 C29 1.437(16) . ?
C28 H28 0.9500 . ?
C29 C30 1.422(15) . ?
C30 C40 1.491(14) . ?
C31 C32 1.392(14) . ?
C31 C40 1.393(15) . ?
C32 C33 1.370(13) . ?
C32 H32 0.9500 . ?
C33 C34 1.409(15) . ?
C33 H33 0.9500 . ?
C34 C35 1.420(14) . ?
C34 C39 1.453(14) . ?
C35 C36 1.324(15) . ?
C35 H35 0.9500 . ?
C36 C37 1.393(16) . ?
C37 C38 1.383(15) . ?
C37 H37 0.9500 . ?
C38 C39 1.413(14) . ?
C38 H38 0.9500 . ?
C39 C40 1.442(13) . ?
C41 C42 1.53(2) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C43 1.55(3) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.54(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.42(3) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.55(2) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O1 B1 124.6(8) . . ?
C31 O2 B1 119.3(8) . . ?
C1 N1 C4 108.1(8) . . ?
C1 N1 B1 125.8(8) . . ?
C4 N1 B1 126.0(8) . . ?
C9 N2 C6 106.2(9) . . ?
C9 N2 B1 129.3(9) . . ?
C6 N2 B1 124.5(8) . . ?
N1 C1 C2 109.1(9) . . ?
N1 C1 C10 124.7(9) . . ?
C2 C1 C10 126.1(9) . . ?
C3 C2 C1 107.9(9) . . ?
C3 C2 C11 125.6(10) . . ?
C1 C2 C11 126.5(10) . . ?
C2 C3 C4 106.7(9) . . ?
C2 C3 C17 123.8(9) . . ?
C4 C3 C17 129.4(10) . . ?
C5 C4 N1 120.6(9) . . ?
C5 C4 C3 131.2(10) . . ?
N1 C4 C3 108.1(9) . . ?
C4 C5 C6 122.5(10) . . ?
C4 C5 C18 119.2(9) . . ?
C6 C5 C18 118.3(10) . . ?
C5 C6 N2 120.0(10) . . ?
C5 C6 C7 132.1(11) . . ?
N2 C6 C7 107.5(9) . . ?
C8 C7 C6 106.1(10) . . ?
C8 C7 C19 125.1(11) . . ?
C6 C7 C19 128.8(11) . . ?
C7 C8 C9 110.3(10) . . ?
C7 C8 H8 124.8 . . ?
C9 C8 H8 124.8 . . ?
N2 C9 C8 109.7(9) . . ?
N2 C9 C20 125.7(10) . . ?
C8 C9 C20 124.6(10) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.2(11) . . ?
C12 C11 C2 121.6(11) . . ?
C16 C11 C2 119.9(11) . . ?
C11 C12 C13 119.9(13) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 122.4(14) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C13 C14 C15 118.9(13) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 121.1(14) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 119.4(14) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?
C3 C17 H17A 109.5 . . ?
C3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C19 H19A 109.5 . . ?
C7 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C7 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 C30 123.2(10) . . ?
O1 C21 C22 117.2(9) . . ?
C30 C21 C22 119.4(10) . . ?
C23 C22 C21 121.0(11) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 119.7(12) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C29 C24 C23 119.0(10) . . ?
C29 C24 C25 119.2(12) . . ?
C23 C24 C25 121.8(12) . . ?
C26 C25 C24 120.3(13) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C25 C26 C27 122.5(13) . . ?
C25 C26 Br1 119.5(12) . . ?
C27 C26 Br1 118.0(11) . . ?
C26 C27 C28 119.5(13) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C27 C28 C29 120.5(12) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C24 C29 C30 120.0(10) . . ?
C24 C29 C28 117.8(10) . . ?
C30 C29 C28 122.1(10) . . ?
C21 C30 C29 120.0(10) . . ?
C21 C30 C40 120.1(9) . . ?
C29 C30 C40 119.8(10) . . ?
O2 C31 C32 119.3(9) . . ?
O2 C31 C40 120.5(9) . . ?
C32 C31 C40 120.2(9) . . ?
C33 C32 C31 122.4(10) . . ?
C33 C32 H32 118.8 . . ?
C31 C32 H32 118.8 . . ?
C32 C33 C34 119.6(10) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C33 C34 C35 123.1(10) . . ?
C33 C34 C39 118.9(9) . . ?
C35 C34 C39 117.9(10) . . ?
C36 C35 C34 120.5(10) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C37 123.7(10) . . ?
C35 C36 Br2 119.1(8) . . ?
C37 C36 Br2 117.2(9) . . ?
C38 C37 C36 118.4(11) . . ?
C38 C37 H37 120.8 . . ?
C36 C37 H37 120.8 . . ?
C37 C38 C39 121.1(10) . . ?
C37 C38 H38 119.4 . . ?
C39 C38 H38 119.4 . . ?
C38 C39 C40 122.6(10) . . ?
C38 C39 C34 118.3(9) . . ?
C40 C39 C34 118.9(9) . . ?
C31 C40 C39 118.1(9) . . ?
C31 C40 C30 121.7(8) . . ?
C39 C40 C30 119.6(10) . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C42 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C41 C42 C43 115(2) . . ?
C41 C42 H42A 108.4 . . ?
C43 C42 H42A 108.4 . . ?
C41 C42 H42B 108.4 . . ?
C43 C42 H42B 108.4 . . ?
H42A C42 H42B 107.5 . . ?
C44 C43 C42 119(2) . . ?
C44 C43 H43A 107.7 . . ?
C42 C43 H43A 107.7 . . ?
C44 C43 H43B 107.7 . . ?
C42 C43 H43B 107.7 . . ?
H43A C43 H43B 107.1 . . ?
C45 C44 C43 115(2) . . ?
C45 C44 H44A 108.6 . . ?
C43 C44 H44A 108.6 . . ?
C45 C44 H44B 108.6 . . ?
C43 C44 H44B 108.6 . . ?
H44A C44 H44B 107.6 . . ?
C44 C45 C46 114(2) . . ?
C44 C45 H45A 108.7 . . ?
C46 C45 H45A 108.7 . . ?
C44 C45 H45B 108.7 . . ?
C46 C45 H45B 108.7 . . ?
H45A C45 H45B 107.6 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O2 B1 O1 116.3(9) . . ?
O2 B1 N1 104.9(7) . . ?
O1 B1 N1 113.8(8) . . ?
O2 B1 N2 112.3(8) . . ?
O1 B1 N2 103.3(7) . . ?
N1 B1 N2 105.8(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -0.6(10) . . . . ?
B1 N1 C1 C2 178.8(8) . . . . ?
C4 N1 C1 C10 177.3(9) . . . . ?
B1 N1 C1 C10 -3.3(15) . . . . ?
N1 C1 C2 C3 -0.2(10) . . . . ?
C10 C1 C2 C3 -178.0(9) . . . . ?
N1 C1 C2 C11 179.1(10) . . . . ?
C10 C1 C2 C11 1.3(16) . . . . ?
C1 C2 C3 C4 0.8(10) . . . . ?
C11 C2 C3 C4 -178.5(10) . . . . ?
C1 C2 C3 C17 178.5(9) . . . . ?
C11 C2 C3 C17 -0.8(15) . . . . ?
C1 N1 C4 C5 -175.4(9) . . . . ?
B1 N1 C4 C5 5.2(14) . . . . ?
C1 N1 C4 C3 1.1(10) . . . . ?
B1 N1 C4 C3 -178.3(8) . . . . ?
C2 C3 C4 C5 174.7(10) . . . . ?
C17 C3 C4 C5 -2.7(18) . . . . ?
C2 C3 C4 N1 -1.2(11) . . . . ?
C17 C3 C4 N1 -178.7(9) . . . . ?
N1 C4 C5 C6 0.4(15) . . . . ?
C3 C4 C5 C6 -175.1(10) . . . . ?
N1 C4 C5 C18 -178.8(8) . . . . ?
C3 C4 C5 C18 5.7(16) . . . . ?
C4 C5 C6 N2 -6.8(15) . . . . ?
C18 C5 C6 N2 172.3(8) . . . . ?
C4 C5 C6 C7 -179.4(9) . . . . ?
C18 C5 C6 C7 -0.3(17) . . . . ?
C9 N2 C6 C5 -170.8(9) . . . . ?
B1 N2 C6 C5 8.1(14) . . . . ?
C9 N2 C6 C7 3.5(10) . . . . ?
B1 N2 C6 C7 -177.6(8) . . . . ?
C5 C6 C7 C8 172.1(11) . . . . ?
N2 C6 C7 C8 -1.1(11) . . . . ?
C5 C6 C7 C19 -9.3(18) . . . . ?
N2 C6 C7 C19 177.4(9) . . . . ?
C6 C7 C8 C9 -1.6(11) . . . . ?
C19 C7 C8 C9 179.8(9) . . . . ?
C6 N2 C9 C8 -4.5(11) . . . . ?
B1 N2 C9 C8 176.7(9) . . . . ?
C6 N2 C9 C20 173.4(9) . . . . ?
B1 N2 C9 C20 -5.4(16) . . . . ?
C7 C8 C9 N2 4.0(12) . . . . ?
C7 C8 C9 C20 -173.9(9) . . . . ?
C3 C2 C11 C12 118.3(12) . . . . ?
C1 C2 C11 C12 -60.9(15) . . . . ?
C3 C2 C11 C16 -55.5(16) . . . . ?
C1 C2 C11 C16 125.3(12) . . . . ?
C16 C11 C12 C13 2.2(18) . . . . ?
C2 C11 C12 C13 -171.7(12) . . . . ?
C11 C12 C13 C14 -4(2) . . . . ?
C12 C13 C14 C15 2(2) . . . . ?
C13 C14 C15 C16 0(2) . . . . ?
C14 C15 C16 C11 -1(2) . . . . ?
C12 C11 C16 C15 0.2(19) . . . . ?
C2 C11 C16 C15 174.2(11) . . . . ?
B1 O1 C21 C30 51.0(13) . . . . ?
B1 O1 C21 C22 -133.3(10) . . . . ?
O1 C21 C22 C23 179.2(9) . . . . ?
C30 C21 C22 C23 -4.8(14) . . . . ?
C21 C22 C23 C24 -3.4(15) . . . . ?
C22 C23 C24 C29 6.0(16) . . . . ?
C22 C23 C24 C25 -174.2(10) . . . . ?
C29 C24 C25 C26 -2.2(18) . . . . ?
C23 C24 C25 C26 178.0(12) . . . . ?
C24 C25 C26 C27 0(2) . . . . ?
C24 C25 C26 Br1 178.9(9) . . . . ?
C25 C26 C27 C28 0(2) . . . . ?
Br1 C26 C27 C28 -178.2(9) . . . . ?
C26 C27 C28 C29 0.9(18) . . . . ?
C23 C24 C29 C30 -0.7(16) . . . . ?
C25 C24 C29 C30 179.5(10) . . . . ?
C23 C24 C29 C28 -176.9(10) . . . . ?
C25 C24 C29 C28 3.3(16) . . . . ?
C27 C28 C29 C24 -2.7(16) . . . . ?
C27 C28 C29 C30 -178.9(10) . . . . ?
O1 C21 C30 C29 -174.1(9) . . . . ?
C22 C21 C30 C29 10.2(14) . . . . ?
O1 C21 C30 C40 8.4(14) . . . . ?
C22 C21 C30 C40 -167.3(9) . . . . ?
C24 C29 C30 C21 -7.6(15) . . . . ?
C28 C29 C30 C21 168.6(9) . . . . ?
C24 C29 C30 C40 170.0(9) . . . . ?
C28 C29 C30 C40 -13.9(15) . . . . ?
B1 O2 C31 C32 -121.0(10) . . . . ?
B1 O2 C31 C40 61.1(13) . . . . ?
O2 C31 C32 C33 173.4(9) . . . . ?
C40 C31 C32 C33 -8.8(15) . . . . ?
C31 C32 C33 C34 -3.4(16) . . . . ?
C32 C33 C34 C35 -168.1(10) . . . . ?
C32 C33 C34 C39 7.7(15) . . . . ?
C33 C34 C35 C36 174.3(11) . . . . ?
C39 C34 C35 C36 -1.5(16) . . . . ?
C34 C35 C36 C37 1.2(19) . . . . ?
C34 C35 C36 Br2 -175.4(9) . . . . ?
C35 C36 C37 C38 1.3(19) . . . . ?
Br2 C36 C37 C38 178.0(9) . . . . ?
C36 C37 C38 C39 -3.4(18) . . . . ?
C37 C38 C39 C40 -173.0(11) . . . . ?
C37 C38 C39 C34 3.0(16) . . . . ?
C33 C34 C39 C38 -176.5(10) . . . . ?
C35 C34 C39 C38 -0.5(15) . . . . ?
C33 C34 C39 C40 -0.3(15) . . . . ?
C35 C34 C39 C40 175.7(10) . . . . ?
O2 C31 C40 C39 -166.3(9) . . . . ?
C32 C31 C40 C39 15.8(15) . . . . ?
O2 C31 C40 C30 5.0(15) . . . . ?
C32 C31 C40 C30 -172.9(9) . . . . ?
C38 C39 C40 C31 164.7(10) . . . . ?
C34 C39 C40 C31 -11.2(14) . . . . ?
C38 C39 C40 C30 -6.8(15) . . . . ?
C34 C39 C40 C30 177.2(9) . . . . ?
C21 C30 C40 C31 -50.6(14) . . . . ?
C29 C30 C40 C31 131.9(10) . . . . ?
C21 C30 C40 C39 120.6(10) . . . . ?
C29 C30 C40 C39 -56.9(13) . . . . ?
C41 C42 C43 C44 179(2) . . . . ?
C42 C43 C44 C45 -177(2) . . . . ?
C43 C44 C45 C46 -174(2) . . . . ?
C31 O2 B1 O1 -46.9(12) . . . . ?
C31 O2 B1 N1 -173.6(8) . . . . ?
C31 O2 B1 N2 71.9(11) . . . . ?
C21 O1 B1 O2 -29.7(13) . . . . ?
C21 O1 B1 N1 92.4(11) . . . . ?
C21 O1 B1 N2 -153.3(8) . . . . ?
C1 N1 B1 O2 58.0(12) . . . . ?
C4 N1 B1 O2 -122.7(9) . . . . ?
C1 N1 B1 O1 -70.3(12) . . . . ?
C4 N1 B1 O1 109.1(10) . . . . ?
C1 N1 B1 N2 177.0(8) . . . . ?
C4 N1 B1 N2 -3.7(12) . . . . ?
C9 N2 B1 O2 -70.3(12) . . . . ?
C6 N2 B1 O2 111.0(10) . . . . ?
C9 N2 B1 O1 55.8(12) . . . . ?
C6 N2 B1 O1 -122.8(9) . . . . ?
C9 N2 B1 N1 175.7(9) . . . . ?
C6 N2 B1 N1 -2.9(12) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
