# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_anti-B2n
_database_code_depnum_ccdc_archive 'CCDC 2095548'
loop_
_audit_author_name
_audit_author_address
'Masashi Nakamura'
;Kyoto university
Japan
;
_audit_update_record             
;
2021-11-14 deposited with the CCDC.	2021-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H48 B2 F2 N4 O4'
_chemical_formula_sum            'C40 H48 B2 F2 N4 O4'
_chemical_formula_weight         708.44

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'
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'
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'

_space_group_crystal_system      Monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/a'
_space_group_name_Hall           '-P 2yab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   12.864(4)
_cell_length_b                   9.016(3)
_cell_length_c                   15.507(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.242(4)
_cell_angle_gamma                90
_cell_volume                     1791.0(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    4166
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            14061
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.124
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4094
_reflns_number_gt                3022
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0418P)²+0.3152P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4094
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1268
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.71615(14) -0.28637(19) 0.16686(12) 0.0185(4) Uani 1 1 d . . . . .
C2 C 0.64691(14) -0.2685(2) 0.23086(12) 0.0202(4) Uani 1 1 d . . . . .
C3 C 0.59476(15) -0.3962(2) 0.25461(13) 0.0236(4) Uani 1 1 d . . . . .
H3 H 0.5467 -0.3890 0.2974 0.028 Uiso 1 1 calc R U . . .
C4 C 0.61107(16) -0.5319(2) 0.21776(13) 0.0249(5) Uani 1 1 d . . . . .
H4 H 0.5740 -0.6164 0.2350 0.030 Uiso 1 1 calc R U . . .
C5 C 0.68139(15) -0.5465(2) 0.15547(13) 0.0233(4) Uani 1 1 d . . . . .
H5 H 0.6933 -0.6409 0.1309 0.028 Uiso 1 1 calc R U . . .
C6 C 0.73356(14) -0.4242(2) 0.12954(12) 0.0209(4) Uani 1 1 d . . . . .
H6 H 0.7812 -0.4331 0.0865 0.025 Uiso 1 1 calc R U . . .
C7 C 0.89044(14) -0.04583(19) 0.06747(12) 0.0190(4) Uani 1 1 d . . . . .
C8 C 0.85958(15) 0.0959(2) 0.09151(12) 0.0214(4) Uani 1 1 d . . . . .
C9 C 0.91198(15) 0.2210(2) 0.06314(13) 0.0235(4) Uani 1 1 d . . . . .
H9 H 0.8920 0.3172 0.0803 0.028 Uiso 1 1 calc R U . . .
C10 C 0.99120(15) 0.2056(2) 0.01120(13) 0.0224(4) Uani 1 1 d . . . . .
H10 H 1.0246 0.2917 -0.0083 0.027 Uiso 1 1 calc R U . . .
C11 C 0.97524(14) -0.0637(2) 0.01429(12) 0.0194(4) Uani 1 1 d . . . . .
C12 C 0.63591(15) -0.1242(2) 0.28086(12) 0.0202(4) Uani 1 1 d . . . . .
C13 C 0.68542(15) -0.1460(2) 0.37414(12) 0.0232(4) Uani 1 1 d . . . . .
H13 H 0.6803 -0.0516 0.4061 0.028 Uiso 1 1 calc R U . . .
H13A H 0.6447 -0.2215 0.4029 0.028 Uiso 1 1 calc R U . . .
C14 C 0.79951(16) -0.1943(2) 0.38042(14) 0.0287(5) Uani 1 1 d . . . . .
H14 H 0.8049 -0.2867 0.3466 0.034 Uiso 1 1 calc R U . . .
H14A H 0.8406 -0.1170 0.3535 0.034 Uiso 1 1 calc R U . . .
C15 C 0.84765(17) -0.2213(2) 0.47239(14) 0.0320(5) Uani 1 1 d . . . . .
H15 H 0.8065 -0.2988 0.4992 0.038 Uiso 1 1 calc R U . . .
H15A H 0.9193 -0.2602 0.4698 0.038 Uiso 1 1 calc R U . . .
C16 C 0.85291(19) -0.0855(3) 0.53014(15) 0.0409(6) Uani 1 1 d . . . . .
H16 H 0.8847 -0.1123 0.5879 0.061 Uiso 1 1 calc R U . . .
H16A H 0.8952 -0.0089 0.5052 0.061 Uiso 1 1 calc R U . . .
H16B H 0.7822 -0.0475 0.5347 0.061 Uiso 1 1 calc R U . . .
C17 C 0.52074(15) -0.0780(2) 0.27853(13) 0.0237(4) Uani 1 1 d . . . . .
H17 H 0.4934 -0.0619 0.2175 0.028 Uiso 1 1 calc R U . . .
H17A H 0.4807 -0.1606 0.3014 0.028 Uiso 1 1 calc R U . . .
C18 C 0.50168(15) 0.0616(2) 0.32997(14) 0.0273(5) Uani 1 1 d . . . . .
H18 H 0.5131 0.0385 0.3925 0.033 Uiso 1 1 calc R U . . .
H18A H 0.5533 0.1378 0.3169 0.033 Uiso 1 1 calc R U . . .
C19 C 0.39305(16) 0.1247(2) 0.31071(15) 0.0313(5) Uani 1 1 d . . . . .
H19 H 0.3414 0.0481 0.3233 0.038 Uiso 1 1 calc R U . . .
H19A H 0.3819 0.1485 0.2482 0.038 Uiso 1 1 calc R U . . .
N1 N 0.76549(12) -0.15660(16) 0.13797(10) 0.0200(4) Uani 1 1 d . . . . .
N2 N 0.84543(12) -0.17326(17) 0.09516(10) 0.0197(4) Uani 1 1 d . . . . .
O1 O 0.69285(10) -0.00482(14) 0.24619(8) 0.0218(3) Uani 1 1 d . . . . .
O2 O 0.78389(11) 0.11566(14) 0.14310(9) 0.0274(3) Uani 1 1 d . . . . .
F1 F 0.62359(9) 0.00560(12) 0.09900(8) 0.0314(3) Uani 1 1 d . . . . .
C20 C 0.37343(17) 0.2628(2) 0.36231(17) 0.0381(6) Uani 1 1 d . . . . .
H20 H 0.3020 0.2978 0.3468 0.057 Uiso 1 1 calc R U . . .
H20A H 0.3825 0.2397 0.4243 0.057 Uiso 1 1 calc R U . . .
H20B H 0.4231 0.3402 0.3492 0.057 Uiso 1 1 calc R U . . .
B1 B 0.71136(18) -0.0040(2) 0.15866(15) 0.0218(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
C1 C6 1.398(2) . ?
C1 C2 1.402(3) . ?
C1 N1 1.423(2) . ?
C2 C3 1.399(3) . ?
C2 C12 1.527(3) . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.373(2) . ?
C7 C8 1.398(3) . ?
C7 C11 1.435(3) . ?
C8 O2 1.327(2) . ?
C8 C9 1.405(3) . ?
C9 C10 1.362(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.418(3) 3_755 ?
C10 H10 0.9500 . ?
C11 C11 1.405(4) 3_755 ?
C11 C10 1.418(3) 3_755 ?
C12 O1 1.434(2) . ?
C12 C17 1.536(3) . ?
C12 C13 1.539(3) . ?
C13 C14 1.525(3) . ?
C13 H13 0.9900 . ?
C13 H13A 0.9900 . ?
C14 C15 1.522(3) . ?
C14 H14 0.9900 . ?
C14 H14A 0.9900 . ?
C15 C16 1.515(3) . ?
C15 H15 0.9900 . ?
C15 H15A 0.9900 . ?
C16 H16 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 C18 1.521(3) . ?
C17 H17 0.9900 . ?
C17 H17A 0.9900 . ?
C18 C19 1.513(3) . ?
C18 H18 0.9900 . ?
C18 H18A 0.9900 . ?
C19 C20 1.513(3) . ?
C19 H19 0.9900 . ?
C19 H19A 0.9900 . ?
N1 N2 1.283(2) . ?
N1 B1 1.588(3) . ?
O1 B1 1.399(3) . ?
O2 B1 1.461(3) . ?
F1 B1 1.395(3) . ?
C20 H20 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 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
C6 C1 C2 122.12(17) . . ?
C6 C1 N1 120.52(17) . . ?
C2 C1 N1 117.30(16) . . ?
C3 C2 C1 116.26(17) . . ?
C3 C2 C12 119.89(17) . . ?
C1 C2 C12 123.49(17) . . ?
C4 C3 C2 121.89(19) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.48(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.71(18) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 119.52(18) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 C7 C8 122.88(17) . . ?
N2 C7 C11 116.73(16) . . ?
C8 C7 C11 120.34(17) . . ?
O2 C8 C7 121.68(17) . . ?
O2 C8 C9 118.68(17) . . ?
C7 C8 C9 119.60(17) . . ?
C10 C9 C8 120.62(18) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 121.34(18) . 3_755 ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 3_755 . ?
C11 C11 C10 119.4(2) 3_755 3_755 ?
C11 C11 C7 118.6(2) 3_755 . ?
C10 C11 C7 121.90(17) 3_755 . ?
O1 C12 C2 112.01(15) . . ?
O1 C12 C17 108.17(15) . . ?
C2 C12 C17 110.68(15) . . ?
O1 C12 C13 105.44(15) . . ?
C2 C12 C13 108.61(15) . . ?
C17 C12 C13 111.84(16) . . ?
C14 C13 C12 114.18(16) . . ?
C14 C13 H13 108.7 . . ?
C12 C13 H13 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
H13 C13 H13A 107.6 . . ?
C15 C14 C13 114.35(17) . . ?
C15 C14 H14 108.7 . . ?
C13 C14 H14 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
H14 C14 H14A 107.6 . . ?
C16 C15 C14 114.65(18) . . ?
C16 C15 H15 108.6 . . ?
C14 C15 H15 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15A 108.6 . . ?
H15 C15 H15A 107.6 . . ?
C15 C16 H16 109.5 . . ?
C15 C16 H16A 109.5 . . ?
H16 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C18 C17 C12 114.42(16) . . ?
C18 C17 H17 108.7 . . ?
C12 C17 H17 108.7 . . ?
C18 C17 H17A 108.7 . . ?
C12 C17 H17A 108.7 . . ?
H17 C17 H17A 107.6 . . ?
C19 C18 C17 113.44(17) . . ?
C19 C18 H18 108.9 . . ?
C17 C18 H18 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
H18 C18 H18A 107.7 . . ?
C18 C19 C20 113.62(18) . . ?
C18 C19 H19 108.8 . . ?
C20 C19 H19 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
H19 C19 H19A 107.7 . . ?
N2 N1 C1 117.93(15) . . ?
N2 N1 B1 126.38(15) . . ?
C1 N1 B1 115.62(15) . . ?
N1 N2 C7 116.41(16) . . ?
B1 O1 C12 120.36(15) . . ?
C8 O2 B1 120.98(15) . . ?
C19 C20 H20 109.5 . . ?
C19 C20 H20A 109.5 . . ?
H20 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
F1 B1 O1 116.38(17) . . ?
F1 B1 O2 109.57(17) . . ?
O1 B1 O2 109.38(17) . . ?
F1 B1 N1 105.26(16) . . ?
O1 B1 N1 107.95(16) . . ?
O2 B1 N1 107.95(16) . . ?

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
C6 C1 C2 C3 -0.9(3) . . . . ?
N1 C1 C2 C3 176.41(16) . . . . ?
C6 C1 C2 C12 172.21(17) . . . . ?
N1 C1 C2 C12 -10.5(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C12 C2 C3 C4 -172.88(18) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
N1 C1 C6 C5 -176.89(17) . . . . ?
N2 C7 C8 O2 -0.1(3) . . . . ?
C11 C7 C8 O2 -177.60(18) . . . . ?
N2 C7 C8 C9 177.65(18) . . . . ?
C11 C7 C8 C9 0.1(3) . . . . ?
O2 C8 C9 C10 179.00(18) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C8 C9 C10 C11 -1.4(3) . . . 3_755 ?
N2 C7 C11 C11 -178.9(2) . . . 3_755 ?
C8 C7 C11 C11 -1.3(3) . . . 3_755 ?
N2 C7 C11 C10 2.2(3) . . . 3_755 ?
C8 C7 C11 C10 179.87(18) . . . 3_755 ?
C3 C2 C12 O1 -178.72(17) . . . . ?
C1 C2 C12 O1 8.4(3) . . . . ?
C3 C2 C12 C17 -57.9(2) . . . . ?
C1 C2 C12 C17 129.22(19) . . . . ?
C3 C2 C12 C13 65.2(2) . . . . ?
C1 C2 C12 C13 -107.6(2) . . . . ?
O1 C12 C13 C14 -63.5(2) . . . . ?
C2 C12 C13 C14 56.7(2) . . . . ?
C17 C12 C13 C14 179.14(16) . . . . ?
C12 C13 C14 C15 -177.91(17) . . . . ?
C13 C14 C15 C16 -63.1(3) . . . . ?
O1 C12 C17 C18 -59.4(2) . . . . ?
C2 C12 C17 C18 177.58(17) . . . . ?
C13 C12 C17 C18 56.3(2) . . . . ?
C12 C17 C18 C19 166.85(17) . . . . ?
C17 C18 C19 C20 179.50(19) . . . . ?
C6 C1 N1 N2 -18.3(3) . . . . ?
C2 C1 N1 N2 164.38(17) . . . . ?
C6 C1 N1 B1 158.83(17) . . . . ?
C2 C1 N1 B1 -18.5(2) . . . . ?
C1 N1 N2 C7 179.32(16) . . . . ?
B1 N1 N2 C7 2.6(3) . . . . ?
C8 C7 N2 N1 6.7(3) . . . . ?
C11 C7 N2 N1 -175.68(16) . . . . ?
C2 C12 O1 B1 27.5(2) . . . . ?
C17 C12 O1 B1 -94.7(2) . . . . ?
C13 C12 O1 B1 145.49(17) . . . . ?
C7 C8 O2 B1 -16.4(3) . . . . ?
C9 C8 O2 B1 165.90(18) . . . . ?
C12 O1 B1 F1 64.0(2) . . . . ?
C12 O1 B1 O2 -171.25(14) . . . . ?
C12 O1 B1 N1 -54.0(2) . . . . ?
C8 O2 B1 F1 -92.1(2) . . . . ?
C8 O2 B1 O1 139.20(18) . . . . ?
C8 O2 B1 N1 22.0(2) . . . . ?
N2 N1 B1 F1 100.9(2) . . . . ?
C1 N1 B1 F1 -75.95(19) . . . . ?
N2 N1 B1 O1 -134.21(18) . . . . ?
C1 N1 B1 O1 49.0(2) . . . . ?
N2 N1 B1 O2 -16.1(3) . . . . ?
C1 N1 B1 O2 167.09(16) . . . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.048


_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_anti-B2b
_database_code_depnum_ccdc_archive 'CCDC 2095549'
loop_
_audit_author_name
_audit_author_address
'Masashi Nakamura'
;Kyoto university
Japan
;
_audit_update_record             
;
2021-11-14 deposited with the CCDC.	2021-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H50 B2 F2 N4 O4'
_chemical_formula_sum            'C44 H50 B2 F2 N4 O4'
_chemical_formula_weight         758.50

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'
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.656(6)
_cell_length_b                   21.051(15)
_cell_length_c                   12.118(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.077(11)
_cell_angle_gamma                90
_cell_volume                     1942(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    3173
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            15609
_diffrn_reflns_av_unetI/netI     0.1864
_diffrn_reflns_av_R_equivalents  0.1255
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.162
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4407
_reflns_number_gt                2145
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0181P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4407
_refine_ls_number_parameters     362
_refine_ls_number_restraints     232
_refine_ls_R_factor_all          0.1594
_refine_ls_R_factor_gt           0.0608
_refine_ls_wR_factor_ref         0.0981
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_restrained_S_all      0.892
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5896(2) 0.48571(10) 0.41056(17) 0.0192(5) Uani 1 1 d . . . . .
C2 C 0.6060(2) 0.44391(10) 0.50127(18) 0.0186(5) Uani 1 1 d . . . . .
C3 C 0.4859(2) 0.54024(10) 0.41016(18) 0.0228(5) Uani 1 1 d . . . . .
H13 H 0.478188 0.567360 0.347165 0.027 Uiso 1 1 calc R U . . .
C4A C 0.720(2) 0.4945(6) 0.1391(8) 0.0209(19) Uani 0.56(2) 1 d D . P A 1
C5A C 0.8017(18) 0.4360(6) 0.1300(7) 0.0236(19) Uani 0.56(2) 1 d D . P A 1
C6A C 0.8528(15) 0.4169(5) 0.0240(8) 0.035(2) Uani 0.56(2) 1 d D . P A 1
H1 H 0.905782 0.376658 0.015713 0.043 Uiso 0.56(2) 1 calc R U P A 1
C7A C 0.8245(13) 0.4572(6) -0.0650(7) 0.033(2) Uani 0.56(2) 1 d D . P A 1
H2 H 0.857359 0.443476 -0.134539 0.040 Uiso 0.56(2) 1 calc R U P A 1
C8A C 0.7490(14) 0.5181(7) -0.0585(6) 0.032(2) Uani 0.56(2) 1 d D . P A 1
C9A C 0.7292(13) 0.5591(8) -0.1512(7) 0.041(3) Uani 0.56(2) 1 d D . P A 1
H3 H 0.765934 0.546297 -0.220246 0.050 Uiso 0.56(2) 1 calc R U P A 1
C10A C 0.6564(14) 0.6175(7) -0.1396(7) 0.043(2) Uani 0.56(2) 1 d D . P A 1
H4 H 0.642258 0.645238 -0.201724 0.052 Uiso 0.56(2) 1 calc R U P A 1
C11A C 0.6019(16) 0.6376(6) -0.0385(9) 0.041(2) Uani 0.56(2) 1 d D . P A 1
H5 H 0.553518 0.678868 -0.032873 0.049 Uiso 0.56(2) 1 calc R U P A 1
C12A C 0.6176(18) 0.5985(6) 0.0525(9) 0.032(2) Uani 0.56(2) 1 d D . P A 1
H6 H 0.574922 0.611612 0.119702 0.039 Uiso 0.56(2) 1 calc R U P A 1
C4B C 0.750(2) 0.4786(7) 0.1405(9) 0.016(2) Uani 0.44(2) 1 d D . P A 2
C6B C 0.8781(16) 0.3935(7) 0.0394(9) 0.026(2) Uani 0.44(2) 1 d D . P A 2
H7 H 0.925484 0.351887 0.036520 0.031 Uiso 0.44(2) 1 calc R U P A 2
C7B C 0.8541(17) 0.4302(7) -0.0530(10) 0.028(2) Uani 0.44(2) 1 d D . P A 2
H8 H 0.890368 0.413641 -0.119901 0.034 Uiso 0.44(2) 1 calc R U P A 2
C12B C 0.647(2) 0.5777(7) 0.0395(10) 0.024(2) Uani 0.44(2) 1 d D . P A 2
H9 H 0.612262 0.595337 0.105851 0.029 Uiso 0.44(2) 1 calc R U P A 2
C13A C 0.6976(15) 0.5385(6) 0.0453(6) 0.0230(19) Uani 0.56(2) 1 d D . P A 1
O2B O 0.8592(17) 0.3839(6) 0.2300(8) 0.0250(19) Uani 0.44(2) 1 d D . P A 2
C5B C 0.830(2) 0.4189(7) 0.1403(9) 0.019(2) Uani 0.44(2) 1 d D . P A 2
C8B C 0.7780(15) 0.4918(6) -0.0560(7) 0.022(2) Uani 0.44(2) 1 d D . P A 2
C9B C 0.7632(17) 0.5283(8) -0.1528(8) 0.033(2) Uani 0.44(2) 1 d D . P A 2
H10 H 0.802662 0.511573 -0.218595 0.040 Uiso 0.44(2) 1 calc R U P A 2
C10B C 0.6925(17) 0.5879(8) -0.1536(10) 0.034(3) Uani 0.44(2) 1 d D . P A 2
H11 H 0.685867 0.612465 -0.219631 0.040 Uiso 0.44(2) 1 calc R U P A 2
C11B C 0.6297(19) 0.6131(7) -0.0586(11) 0.036(3) Uani 0.44(2) 1 d D . P A 2
H12 H 0.575896 0.653857 -0.060761 0.043 Uiso 0.44(2) 1 calc R U P A 2
C13B C 0.716(2) 0.5162(6) 0.0399(8) 0.021(2) Uani 0.44(2) 1 d D . P A 2
C14 C 0.7126(3) 0.38234(10) 0.5051(2) 0.0252(6) Uani 1 1 d . . . . .
C15 C 0.8643(3) 0.38839(10) 0.59817(19) 0.0292(6) Uani 1 1 d . . . . .
H14 H 0.939018 0.424626 0.580645 0.035 Uiso 1 1 calc R U . . .
H15 H 0.814259 0.398670 0.668092 0.035 Uiso 1 1 calc R U . . .
C16 C 0.9804(3) 0.32990(11) 0.6178(2) 0.0331(6) Uani 1 1 d . . . . .
H16 H 0.906954 0.293314 0.635391 0.040 Uiso 1 1 calc R U . . .
H17 H 1.033340 0.319744 0.548835 0.040 Uiso 1 1 calc R U . . .
C17 C 1.1253(3) 0.33920(12) 0.7114(2) 0.0450(7) Uani 1 1 d . . . . .
H18 H 1.073484 0.356445 0.776581 0.054 Uiso 1 1 calc R U . . .
H19 H 1.209141 0.371114 0.688257 0.054 Uiso 1 1 calc R U . . .
C18 C 1.2255(3) 0.27872(12) 0.7457(2) 0.0531(9) Uani 1 1 d . . . . .
H20 H 1.316825 0.288213 0.806297 0.080 Uiso 1 1 calc R U . . .
H21 H 1.144150 0.247149 0.770587 0.080 Uiso 1 1 calc R U . . .
H22 H 1.279970 0.261835 0.682158 0.080 Uiso 1 1 calc R U . . .
C19 C 0.5932(3) 0.32568(10) 0.5237(2) 0.0314(6) Uani 1 1 d . . . . .
H23 H 0.662360 0.286042 0.521668 0.038 Uiso 1 1 calc R U . . .
H24 H 0.553292 0.329199 0.598569 0.038 Uiso 1 1 calc R U . . .
C20 C 0.4324(3) 0.32091(11) 0.4381(2) 0.0370(7) Uani 1 1 d . . . . .
H25 H 0.343851 0.352404 0.456454 0.044 Uiso 1 1 calc R U . . .
H26 H 0.467235 0.331772 0.364044 0.044 Uiso 1 1 calc R U . . .
C21 C 0.3494(3) 0.25510(12) 0.4331(2) 0.0457(7) Uani 1 1 d . . . . .
H27 H 0.438858 0.223550 0.416478 0.055 Uiso 1 1 calc R U . . .
H28 H 0.312571 0.244654 0.506899 0.055 Uiso 1 1 calc R U . . .
C22 C 0.1918(3) 0.24947(15) 0.3467(2) 0.0668(10) Uani 1 1 d . . . . .
H29 H 0.144462 0.206232 0.347590 0.100 Uiso 1 1 calc R U . . .
H30 H 0.101266 0.279828 0.363647 0.100 Uiso 1 1 calc R U . . .
H31 H 0.227651 0.258707 0.273157 0.100 Uiso 1 1 calc R U . . .
N1 N 0.6852(2) 0.47142(9) 0.31911(15) 0.0246(5) Uani 1 1 d D . . . .
N2B N 0.662(2) 0.5011(7) 0.2247(8) 0.021(2) Uani 0.44(2) 1 d D U P A 2
N2A N 0.6459(19) 0.5105(5) 0.2355(6) 0.023(2) Uani 0.56(2) 1 d D U P A 1
O1 O 0.78040(18) 0.36933(7) 0.40204(13) 0.0298(4) Uani 1 1 d . . . . .
O2A O 0.8231(15) 0.3957(5) 0.2141(7) 0.0259(15) Uani 0.56(2) 1 d D . P A 1
B1 B 0.8310(3) 0.41765(13) 0.3321(3) 0.0292(7) Uani 1 1 d D . . . .
F1 F 0.98764(14) 0.44873(6) 0.36583(11) 0.0352(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
C1 C3 1.395(3) . ?
C1 C2 1.403(3) . ?
C1 N1 1.424(3) . ?
C2 C3 1.385(3) 3_666 ?
C2 C14 1.530(3) . ?
C3 H13 0.9500 . ?
C4A N2A 1.391(8) . ?
C4A C5A 1.392(7) . ?
C4A C13A 1.462(8) . ?
C5A O2A 1.324(7) . ?
C5A C6A 1.439(8) . ?
C6A C7A 1.371(7) . ?
C6A H1 0.9500 . ?
C7A C8A 1.412(7) . ?
C7A H2 0.9500 . ?
C8A C9A 1.412(9) . ?
C8A C13A 1.423(7) . ?
C9A C10A 1.362(8) . ?
C9A H3 0.9500 . ?
C10A C11A 1.402(10) . ?
C10A H4 0.9500 . ?
C11A C12A 1.371(12) . ?
C11A H5 0.9500 . ?
C12A C13A 1.410(7) . ?
C12A H6 0.9500 . ?
C4B N2B 1.362(10) . ?
C4B C5B 1.401(8) . ?
C4B C13B 1.453(9) . ?
C6B C7B 1.357(9) . ?
C6B C5B 1.417(9) . ?
C6B H7 0.9500 . ?
C7B C8B 1.420(8) . ?
C7B H8 0.9500 . ?
C12B C13B 1.399(8) . ?
C12B C11B 1.399(15) . ?
C12B H9 0.9500 . ?
O2B C5B 1.312(9) . ?
O2B B1 1.462(10) . ?
C8B C13B 1.397(9) . ?
C8B C9B 1.397(9) . ?
C9B C10B 1.365(9) . ?
C9B H10 0.9500 . ?
C10B C11B 1.399(14) . ?
C10B H11 0.9500 . ?
C11B H12 0.9500 . ?
C14 O1 1.429(3) . ?
C14 C19 1.534(3) . ?
C14 C15 1.536(3) . ?
C15 C16 1.522(3) . ?
C15 H14 0.9900 . ?
C15 H15 0.9900 . ?
C16 C17 1.513(3) . ?
C16 H16 0.9900 . ?
C16 H17 0.9900 . ?
C17 C18 1.521(3) . ?
C17 H18 0.9900 . ?
C17 H19 0.9900 . ?
C18 H20 0.9800 . ?
C18 H21 0.9800 . ?
C18 H22 0.9800 . ?
C19 C20 1.527(3) . ?
C19 H23 0.9900 . ?
C19 H24 0.9900 . ?
C20 C21 1.523(3) . ?
C20 H25 0.9900 . ?
C20 H26 0.9900 . ?
C21 C22 1.516(3) . ?
C21 H27 0.9900 . ?
C21 H28 0.9900 . ?
C22 H29 0.9800 . ?
C22 H30 0.9800 . ?
C22 H31 0.9800 . ?
N1 N2B 1.299(6) . ?
N1 N2A 1.315(5) . ?
N1 B1 1.586(3) . ?
O1 B1 1.404(3) . ?
O2A B1 1.499(8) . ?
B1 F1 1.389(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
C3 C1 C2 121.5(2) . . ?
C3 C1 N1 120.7(2) . . ?
C2 C1 N1 117.8(2) . . ?
C3 C2 C1 116.4(2) 3_666 . ?
C3 C2 C14 119.6(2) 3_666 . ?
C1 C2 C14 124.0(2) . . ?
C2 C3 C1 122.1(2) 3_666 . ?
C2 C3 H13 119.0 3_666 . ?
C1 C3 H13 119.0 . . ?
N2A C4A C5A 120.5(7) . . ?
N2A C4A C13A 118.4(6) . . ?
C5A C4A C13A 120.9(6) . . ?
O2A C5A C4A 121.8(7) . . ?
O2A C5A C6A 119.0(7) . . ?
C4A C5A C6A 119.1(6) . . ?
C7A C6A C5A 119.6(6) . . ?
C7A C6A H1 120.2 . . ?
C5A C6A H1 120.2 . . ?
C6A C7A C8A 123.3(6) . . ?
C6A C7A H2 118.3 . . ?
C8A C7A H2 118.3 . . ?
C7A C8A C9A 121.4(7) . . ?
C7A C8A C13A 118.4(6) . . ?
C9A C8A C13A 120.2(6) . . ?
C10A C9A C8A 118.7(8) . . ?
C10A C9A H3 120.7 . . ?
C8A C9A H3 120.7 . . ?
C9A C10A C11A 121.7(8) . . ?
C9A C10A H4 119.2 . . ?
C11A C10A H4 119.2 . . ?
C12A C11A C10A 120.9(7) . . ?
C12A C11A H5 119.6 . . ?
C10A C11A H5 119.6 . . ?
C11A C12A C13A 119.3(8) . . ?
C11A C12A H6 120.3 . . ?
C13A C12A H6 120.3 . . ?
N2B C4B C5B 124.4(8) . . ?
N2B C4B C13B 112.5(7) . . ?
C5B C4B C13B 121.7(8) . . ?
C7B C6B C5B 118.2(7) . . ?
C7B C6B H7 120.9 . . ?
C5B C6B H7 120.9 . . ?
C6B C7B C8B 124.0(8) . . ?
C6B C7B H8 118.0 . . ?
C8B C7B H8 118.0 . . ?
C13B C12B C11B 120.0(8) . . ?
C13B C12B H9 120.0 . . ?
C11B C12B H9 120.0 . . ?
C12A C13A C8A 119.2(6) . . ?
C12A C13A C4A 122.3(6) . . ?
C8A C13A C4A 118.5(6) . . ?
C5B O2B B1 113.7(9) . . ?
O2B C5B C4B 122.5(8) . . ?
O2B C5B C6B 117.9(8) . . ?
C4B C5B C6B 119.6(8) . . ?
C13B C8B C9B 119.4(8) . . ?
C13B C8B C7B 119.2(7) . . ?
C9B C8B C7B 121.3(8) . . ?
C10B C9B C8B 120.6(10) . . ?
C10B C9B H10 119.7 . . ?
C8B C9B H10 119.7 . . ?
C9B C10B C11B 120.9(11) . . ?
C9B C10B H11 119.5 . . ?
C11B C10B H11 119.5 . . ?
C12B C11B C10B 119.1(8) . . ?
C12B C11B H12 120.5 . . ?
C10B C11B H12 120.5 . . ?
C8B C13B C12B 119.9(8) . . ?
C8B C13B C4B 116.9(7) . . ?
C12B C13B C4B 122.6(8) . . ?
O1 C14 C2 112.18(18) . . ?
O1 C14 C19 104.86(18) . . ?
C2 C14 C19 109.81(18) . . ?
O1 C14 C15 109.97(18) . . ?
C2 C14 C15 108.16(18) . . ?
C19 C14 C15 111.89(19) . . ?
C16 C15 C14 115.54(19) . . ?
C16 C15 H14 108.4 . . ?
C14 C15 H14 108.4 . . ?
C16 C15 H15 108.4 . . ?
C14 C15 H15 108.4 . . ?
H14 C15 H15 107.5 . . ?
C17 C16 C15 112.5(2) . . ?
C17 C16 H16 109.1 . . ?
C15 C16 H16 109.1 . . ?
C17 C16 H17 109.1 . . ?
C15 C16 H17 109.1 . . ?
H16 C16 H17 107.8 . . ?
C16 C17 C18 113.9(2) . . ?
C16 C17 H18 108.8 . . ?
C18 C17 H18 108.8 . . ?
C16 C17 H19 108.8 . . ?
C18 C17 H19 108.8 . . ?
H18 C17 H19 107.7 . . ?
C17 C18 H20 109.5 . . ?
C17 C18 H21 109.5 . . ?
H20 C18 H21 109.5 . . ?
C17 C18 H22 109.5 . . ?
H20 C18 H22 109.5 . . ?
H21 C18 H22 109.5 . . ?
C20 C19 C14 113.68(19) . . ?
C20 C19 H23 108.8 . . ?
C14 C19 H23 108.8 . . ?
C20 C19 H24 108.8 . . ?
C14 C19 H24 108.8 . . ?
H23 C19 H24 107.7 . . ?
C21 C20 C19 112.9(2) . . ?
C21 C20 H25 109.0 . . ?
C19 C20 H25 109.0 . . ?
C21 C20 H26 109.0 . . ?
C19 C20 H26 109.0 . . ?
H25 C20 H26 107.8 . . ?
C22 C21 C20 113.4(2) . . ?
C22 C21 H27 108.9 . . ?
C20 C21 H27 108.9 . . ?
C22 C21 H28 108.9 . . ?
C20 C21 H28 108.9 . . ?
H27 C21 H28 107.7 . . ?
C21 C22 H29 109.5 . . ?
C21 C22 H30 109.5 . . ?
H29 C22 H30 109.5 . . ?
C21 C22 H31 109.5 . . ?
H29 C22 H31 109.5 . . ?
H30 C22 H31 109.5 . . ?
N2B N1 C1 123.5(6) . . ?
N2A N1 C1 111.9(5) . . ?
N2B N1 B1 117.3(6) . . ?
N2A N1 B1 128.6(5) . . ?
C1 N1 B1 119.21(19) . . ?
N1 N2B C4B 117.5(9) . . ?
N1 N2A C4A 114.5(7) . . ?
B1 O1 C14 122.51(19) . . ?
C5A O2A B1 121.7(8) . . ?
F1 B1 O1 116.6(2) . . ?
F1 B1 O2B 106.1(6) . . ?
O1 B1 O2B 103.5(6) . . ?
F1 B1 O2A 111.9(5) . . ?
O1 B1 O2A 111.5(5) . . ?
F1 B1 N1 105.7(2) . . ?
O1 B1 N1 109.9(2) . . ?
O2B B1 N1 115.3(5) . . ?
O2A B1 N1 99.7(4) . . ?

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
C3 C1 C2 C3 0.0(3) . . . 3_666 ?
N1 C1 C2 C3 178.79(16) . . . 3_666 ?
C3 C1 C2 C14 177.92(18) . . . . ?
N1 C1 C2 C14 -3.3(3) . . . . ?
C2 C1 C3 C2 0.0(3) . . . 3_666 ?
N1 C1 C3 C2 -178.76(17) . . . 3_666 ?
N2A C4A C5A O2A -5(2) . . . . ?
C13A C4A C5A O2A 179.9(14) . . . . ?
N2A C4A C5A C6A 170.6(15) . . . . ?
C13A C4A C5A C6A -4.9(19) . . . . ?
O2A C5A C6A C7A 177.2(11) . . . . ?
C4A C5A C6A C7A 1.9(17) . . . . ?
C5A C6A C7A C8A 1.0(15) . . . . ?
C6A C7A C8A C9A 177.2(9) . . . . ?
C6A C7A C8A C13A -0.8(15) . . . . ?
C7A C8A C9A C10A -179.6(9) . . . . ?
C13A C8A C9A C10A -1.6(16) . . . . ?
C8A C9A C10A C11A 0.3(17) . . . . ?
C9A C10A C11A C12A -1.1(18) . . . . ?
C10A C11A C12A C13A 3.2(19) . . . . ?
C5B C6B C7B C8B -2(2) . . . . ?
C11A C12A C13A C8A -4.4(17) . . . . ?
C11A C12A C13A C4A 179.6(14) . . . . ?
C7A C8A C13A C12A -178.3(10) . . . . ?
C9A C8A C13A C12A 3.7(15) . . . . ?
C7A C8A C13A C4A -2.2(16) . . . . ?
C9A C8A C13A C4A 179.8(12) . . . . ?
N2A C4A C13A C12A 5(2) . . . . ?
C5A C4A C13A C12A -179.0(12) . . . . ?
N2A C4A C13A C8A -170.6(13) . . . . ?
C5A C4A C13A C8A 5.0(19) . . . . ?
B1 O2B C5B C4B -11(2) . . . . ?
B1 O2B C5B C6B 171.2(13) . . . . ?
N2B C4B C5B O2B -14(3) . . . . ?
C13B C4B C5B O2B -179.0(17) . . . . ?
N2B C4B C5B C6B 164.1(19) . . . . ?
C13B C4B C5B C6B -1(2) . . . . ?
C7B C6B C5B O2B -177.9(13) . . . . ?
C7B C6B C5B C4B 4(2) . . . . ?
C6B C7B C8B C13B -3(2) . . . . ?
C6B C7B C8B C9B 177.4(12) . . . . ?
C13B C8B C9B C10B 1.3(19) . . . . ?
C7B C8B C9B C10B -178.9(12) . . . . ?
C8B C9B C10B C11B -1(2) . . . . ?
C13B C12B C11B C10B -4(2) . . . . ?
C9B C10B C11B C12B 3(2) . . . . ?
C9B C8B C13B C12B -2.6(19) . . . . ?
C7B C8B C13B C12B 177.6(12) . . . . ?
C9B C8B C13B C4B -174.6(14) . . . . ?
C7B C8B C13B C4B 6(2) . . . . ?
C11B C12B C13B C8B 4(2) . . . . ?
C11B C12B C13B C4B 175.5(16) . . . . ?
N2B C4B C13B C8B -170.7(15) . . . . ?
C5B C4B C13B C8B -4(2) . . . . ?
N2B C4B C13B C12B 18(2) . . . . ?
C5B C4B C13B C12B -175.3(14) . . . . ?
C3 C2 C14 O1 172.52(16) 3_666 . . . ?
C1 C2 C14 O1 -5.3(3) . . . . ?
C3 C2 C14 C19 56.3(3) 3_666 . . . ?
C1 C2 C14 C19 -121.5(2) . . . . ?
C3 C2 C14 C15 -66.0(2) 3_666 . . . ?
C1 C2 C14 C15 116.1(2) . . . . ?
O1 C14 C15 C16 -59.9(2) . . . . ?
C2 C14 C15 C16 177.32(19) . . . . ?
C19 C14 C15 C16 56.2(3) . . . . ?
C14 C15 C16 C17 -179.4(2) . . . . ?
C15 C16 C17 C18 170.7(2) . . . . ?
O1 C14 C19 C20 -65.4(2) . . . . ?
C2 C14 C19 C20 55.3(3) . . . . ?
C15 C14 C19 C20 175.42(19) . . . . ?
C14 C19 C20 C21 161.1(2) . . . . ?
C19 C20 C21 C22 -178.8(2) . . . . ?
C3 C1 N1 N2B -11.1(11) . . . . ?
C2 C1 N1 N2B 170.1(11) . . . . ?
C3 C1 N1 N2A -7.3(8) . . . . ?
C2 C1 N1 N2A 173.9(8) . . . . ?
C3 C1 N1 B1 167.44(18) . . . . ?
C2 C1 N1 B1 -11.3(3) . . . . ?
C1 N1 N2B C4B -173.5(12) . . . . ?
B1 N1 N2B C4B 8(2) . . . . ?
C5B C4B N2B N1 14(3) . . . . ?
C13B C4B N2B N1 -179.0(15) . . . . ?
C1 N1 N2A C4A -172.9(11) . . . . ?
B1 N1 N2A C4A 13.0(17) . . . . ?
C5A C4A N2A N1 10(2) . . . . ?
C13A C4A N2A N1 -174.1(12) . . . . ?
C2 C14 O1 B1 33.0(3) . . . . ?
C19 C14 O1 B1 152.15(19) . . . . ?
C15 C14 O1 B1 -87.4(2) . . . . ?
C4A C5A O2A B1 -25.4(17) . . . . ?
C6A C5A O2A B1 159.3(10) . . . . ?
C14 O1 B1 F1 74.1(3) . . . . ?
C14 O1 B1 O2B -169.8(5) . . . . ?
C14 O1 B1 O2A -155.7(5) . . . . ?
C14 O1 B1 N1 -46.1(3) . . . . ?
C5B O2B B1 F1 -85.6(11) . . . . ?
C5B O2B B1 O1 151.1(11) . . . . ?
C5B O2B B1 N1 31.0(13) . . . . ?
C5A O2A B1 F1 -72.3(10) . . . . ?
C5A O2A B1 O1 155.0(9) . . . . ?
C5A O2A B1 N1 39.0(10) . . . . ?
N2B N1 B1 F1 86.0(10) . . . . ?
N2A N1 B1 F1 81.1(9) . . . . ?
C1 N1 B1 F1 -92.7(2) . . . . ?
N2B N1 B1 O1 -147.4(10) . . . . ?
N2A N1 B1 O1 -152.3(9) . . . . ?
C1 N1 B1 O1 34.0(3) . . . . ?
N2B N1 B1 O2B -30.8(12) . . . . ?
C1 N1 B1 O2B 150.5(7) . . . . ?
N2A N1 B1 O2A -35.1(10) . . . . ?
C1 N1 B1 O2A 151.2(5) . . . . ?

_refine_diff_density_max         0.188
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.045


_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_B1
_database_code_depnum_ccdc_archive 'CCDC 2095545'
loop_
_audit_author_name
_audit_author_address
'Masashi Nakamura'
;Kyoto university
Japan
;
_audit_update_record             
;
2021-11-14 deposited with the CCDC.	2021-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H28 B F N2 O2'
_chemical_formula_sum            'C25 H28 B F N2 O2'
_chemical_formula_weight         418.30

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'

_space_group_crystal_system      Monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.670(3)
_cell_length_b                   22.286(7)
_cell_length_c                   11.500(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.990(4)
_cell_angle_gamma                90
_cell_volume                     2188.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    5835
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17659
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.006
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4995
_reflns_number_gt                3954
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, 2000)'
_computing_publication_material  'Yadokari-XG (Wakita, 2000)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+0.2415P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4995
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C7 C 0.37647(17) 0.56945(6) 0.57932(12) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.22929(17) 0.54342(7) 0.58165(13) 0.0217(3) Uani 1 1 d . . . . .
C11 C 0.50401(19) 0.48372(7) 0.69077(13) 0.0247(3) Uani 1 1 d . . . . .
C17 C -0.01743(17) 0.70624(6) 0.35303(13) 0.0214(3) Uani 1 1 d . . . . .
C18 C -0.13329(18) 0.69845(7) 0.23727(13) 0.0242(3) Uani 1 1 d . . . . .
H18 H -0.2382 0.6902 0.2565 0.029 Uiso 1 1 calc R U . . .
H18A H -0.1400 0.7368 0.1934 0.029 Uiso 1 1 calc R U . . .
F1 F 0.10516(10) 0.66535(4) 0.61057(7) 0.0290(2) Uani 1 1 d . . . . .
O1 O -0.01650(11) 0.64903(5) 0.41112(9) 0.0229(2) Uani 1 1 d . . . . .
O2 O 0.09877(12) 0.56984(5) 0.52842(9) 0.0240(2) Uani 1 1 d . . . . .
N1 N 0.26825(14) 0.64766(5) 0.46916(10) 0.0201(3) Uani 1 1 d . . . . .
N2 N 0.39379(14) 0.61869(5) 0.51255(10) 0.0215(3) Uani 1 1 d . . . . .
C5 C 0.44567(19) 0.75583(8) 0.28740(15) 0.0328(4) Uani 1 1 d . . . . .
H5 H 0.5462 0.7675 0.2734 0.039 Uiso 1 1 calc R U . . .
C13 C 0.7857(2) 0.47743(8) 0.74063(15) 0.0336(4) Uani 1 1 d . . . . .
H13 H 0.8772 0.4570 0.7779 0.040 Uiso 1 1 calc R U . . .
C20 C -0.2154(2) 0.64249(8) 0.04575(14) 0.0342(4) Uani 1 1 d . . . . .
H20 H -0.3192 0.6364 0.0685 0.041 Uiso 1 1 calc R U . . .
H20A H -0.2199 0.6803 0.0000 0.041 Uiso 1 1 calc R U . . .
C24 C -0.1873(2) 0.85586(8) 0.46585(16) 0.0385(4) Uani 1 1 d . . . . .
H24 H -0.2886 0.8376 0.4751 0.046 Uiso 1 1 calc R U . . .
H24A H -0.1195 0.8566 0.5446 0.046 Uiso 1 1 calc R U . . .
B1 B 0.1038(2) 0.63430(8) 0.50429(15) 0.0214(4) Uani 1 1 d . . . . .
C1 C 0.28323(17) 0.69448(6) 0.38780(13) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.14657(17) 0.72237(6) 0.33014(12) 0.0208(3) Uani 1 1 d . . . . .
C3 C 0.16612(19) 0.76729(7) 0.24862(14) 0.0261(3) Uani 1 1 d . . . . .
H3 H 0.0762 0.7868 0.2064 0.031 Uiso 1 1 calc R U . . .
C9 C 0.21892(19) 0.48666(7) 0.63452(14) 0.0272(4) Uani 1 1 d . . . . .
H9 H 0.1199 0.4681 0.6327 0.033 Uiso 1 1 calc R U . . .
C4 C 0.31251(19) 0.78392(7) 0.22796(14) 0.0295(4) Uani 1 1 d . . . . .
H4 H 0.3219 0.8148 0.1727 0.035 Uiso 1 1 calc R U . . .
C6 C 0.43163(19) 0.71092(7) 0.36675(15) 0.0290(4) Uani 1 1 d . . . . .
H6 H 0.5223 0.6911 0.4072 0.035 Uiso 1 1 calc R U . . .
C10 C 0.3524(2) 0.45880(7) 0.68821(14) 0.0289(4) Uani 1 1 d . . . . .
H10 H 0.3439 0.4212 0.7255 0.035 Uiso 1 1 calc R U . . .
C12 C 0.6412(2) 0.45385(7) 0.74431(14) 0.0301(4) Uani 1 1 d . . . . .
H12 H 0.6332 0.4168 0.7836 0.036 Uiso 1 1 calc R U . . .
C14 C 0.79911(19) 0.53168(8) 0.68205(14) 0.0310(4) Uani 1 1 d . . . . .
H14 H 0.8999 0.5475 0.6786 0.037 Uiso 1 1 calc R U . . .
C15 C 0.66790(18) 0.56224(7) 0.62945(14) 0.0267(3) Uani 1 1 d . . . . .
H15 H 0.6784 0.5991 0.5901 0.032 Uiso 1 1 calc R U . . .
C16 C 0.51824(18) 0.53922(7) 0.63363(13) 0.0222(3) Uani 1 1 d . . . . .
C19 C -0.09325(19) 0.64897(7) 0.15682(14) 0.0270(4) Uani 1 1 d . . . . .
H19 H -0.0840 0.6105 0.2005 0.032 Uiso 1 1 calc R U . . .
H19A H 0.0096 0.6577 0.1343 0.032 Uiso 1 1 calc R U . . .
C21 C -0.1828(3) 0.59102(9) -0.03210(18) 0.0538(6) Uani 1 1 d . . . . .
H21 H -0.2653 0.5892 -0.1020 0.081 Uiso 1 1 calc R U . . .
H21A H -0.0812 0.5972 -0.0567 0.081 Uiso 1 1 calc R U . . .
H21B H -0.1807 0.5533 0.0119 0.081 Uiso 1 1 calc R U . . .
C22 C -0.07867(18) 0.75371(7) 0.43176(13) 0.0250(3) Uani 1 1 d . . . . .
H22 H -0.1773 0.7382 0.4528 0.030 Uiso 1 1 calc R U . . .
H22A H -0.0018 0.7568 0.5060 0.030 Uiso 1 1 calc R U . . .
C23 C -0.11023(19) 0.81693(7) 0.38296(14) 0.0272(4) Uani 1 1 d . . . . .
H23 H -0.1794 0.8148 0.3050 0.033 Uiso 1 1 calc R U . . .
H23A H -0.0102 0.8356 0.3717 0.033 Uiso 1 1 calc R U . . .
C25 C -0.2155(3) 0.91961(9) 0.4217(2) 0.0605(7) Uani 1 1 d . . . . .
H25 H -0.2649 0.9426 0.4779 0.091 Uiso 1 1 calc R U . . .
H25A H -0.1153 0.9382 0.4141 0.091 Uiso 1 1 calc R U . . .
H25B H -0.2844 0.9192 0.3446 0.091 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
C7 N2 1.3624(18) . ?
C7 C8 1.406(2) . ?
C7 C16 1.445(2) . ?
C8 O2 1.3272(17) . ?
C8 C9 1.413(2) . ?
C11 C12 1.408(2) . ?
C11 C16 1.416(2) . ?
C11 C10 1.422(2) . ?
C17 O1 1.4388(17) . ?
C17 C18 1.532(2) . ?
C17 C2 1.533(2) . ?
C17 C22 1.545(2) . ?
C18 C19 1.518(2) . ?
C18 H18 0.9900 . ?
C18 H18A 0.9900 . ?
F1 B1 1.4029(19) . ?
O1 B1 1.3988(19) . ?
O2 B1 1.465(2) . ?
N1 N2 1.2893(16) . ?
N1 C1 1.4224(19) . ?
N1 B1 1.576(2) . ?
C5 C6 1.374(2) . ?
C5 C4 1.385(2) . ?
C5 H5 0.9500 . ?
C13 C12 1.366(2) . ?
C13 C14 1.399(2) . ?
C13 H13 0.9500 . ?
C20 C21 1.512(2) . ?
C20 C19 1.518(2) . ?
C20 H20 0.9900 . ?
C20 H20A 0.9900 . ?
C24 C25 1.514(3) . ?
C24 C23 1.526(2) . ?
C24 H24 0.9900 . ?
C24 H24A 0.9900 . ?
C1 C6 1.399(2) . ?
C1 C2 1.399(2) . ?
C2 C3 1.402(2) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C9 C10 1.363(2) . ?
C9 H9 0.9500 . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C14 C15 1.373(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.404(2) . ?
C15 H15 0.9500 . ?
C19 H19 0.9900 . ?
C19 H19A 0.9900 . ?
C21 H21 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 C23 1.524(2) . ?
C22 H22 0.9900 . ?
C22 H22A 0.9900 . ?
C23 H23 0.9900 . ?
C23 H23A 0.9900 . ?
C25 H25 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 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
N2 C7 C8 122.15(13) . . ?
N2 C7 C16 116.77(13) . . ?
C8 C7 C16 120.40(13) . . ?
O2 C8 C7 120.81(13) . . ?
O2 C8 C9 118.87(14) . . ?
C7 C8 C9 120.21(14) . . ?
C12 C11 C16 118.73(15) . . ?
C12 C11 C10 122.14(15) . . ?
C16 C11 C10 119.08(14) . . ?
O1 C17 C18 104.65(11) . . ?
O1 C17 C2 110.91(11) . . ?
C18 C17 C2 111.42(12) . . ?
O1 C17 C22 108.03(12) . . ?
C18 C17 C22 110.28(12) . . ?
C2 C17 C22 111.31(12) . . ?
C19 C18 C17 115.29(12) . . ?
C19 C18 H18 108.5 . . ?
C17 C18 H18 108.5 . . ?
C19 C18 H18A 108.5 . . ?
C17 C18 H18A 108.5 . . ?
H18 C18 H18A 107.5 . . ?
B1 O1 C17 120.46(12) . . ?
C8 O2 B1 118.10(12) . . ?
N2 N1 C1 117.04(12) . . ?
N2 N1 B1 123.13(12) . . ?
C1 N1 B1 119.81(12) . . ?
N1 N2 C7 116.95(12) . . ?
C6 C5 C4 119.66(15) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C12 C13 C14 120.03(15) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C21 C20 C19 113.31(15) . . ?
C21 C20 H20 108.9 . . ?
C19 C20 H20 108.9 . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
H20 C20 H20A 107.7 . . ?
C25 C24 C23 112.76(15) . . ?
C25 C24 H24 109.0 . . ?
C23 C24 H24 109.0 . . ?
C25 C24 H24A 109.0 . . ?
C23 C24 H24A 109.0 . . ?
H24 C24 H24A 107.8 . . ?
O1 B1 F1 116.35(13) . . ?
O1 B1 O2 109.41(13) . . ?
F1 B1 O2 108.33(13) . . ?
O1 B1 N1 110.30(12) . . ?
F1 B1 N1 105.02(12) . . ?
O2 B1 N1 106.98(12) . . ?
C6 C1 C2 122.03(14) . . ?
C6 C1 N1 119.85(13) . . ?
C2 C1 N1 118.11(13) . . ?
C1 C2 C3 116.33(13) . . ?
C1 C2 C17 123.29(13) . . ?
C3 C2 C17 120.38(13) . . ?
C4 C3 C2 121.86(15) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C10 C9 C8 119.35(15) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C3 C4 C5 120.38(15) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C5 C6 C1 119.73(15) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C9 C10 C11 122.72(15) . . ?
C9 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
C13 C12 C11 120.96(15) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C15 C14 C13 120.63(16) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.24(15) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 119.38(14) . . ?
C15 C16 C7 122.46(14) . . ?
C11 C16 C7 118.15(14) . . ?
C18 C19 C20 112.46(13) . . ?
C18 C19 H19 109.1 . . ?
C20 C19 H19 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
H19 C19 H19A 107.8 . . ?
C20 C21 H21 109.5 . . ?
C20 C21 H21A 109.5 . . ?
H21 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C23 C22 C17 118.37(12) . . ?
C23 C22 H22 107.7 . . ?
C17 C22 H22 107.7 . . ?
C23 C22 H22A 107.7 . . ?
C17 C22 H22A 107.7 . . ?
H22 C22 H22A 107.1 . . ?
C22 C23 C24 111.45(13) . . ?
C22 C23 H23 109.3 . . ?
C24 C23 H23 109.3 . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23A 109.3 . . ?
H23 C23 H23A 108.0 . . ?
C24 C25 H25 109.5 . . ?
C24 C25 H25A 109.5 . . ?
H25 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?

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
N2 C7 C8 O2 -7.4(2) . . . . ?
C16 C7 C8 O2 -177.61(13) . . . . ?
N2 C7 C8 C9 168.57(13) . . . . ?
C16 C7 C8 C9 -1.7(2) . . . . ?
O1 C17 C18 C19 -58.86(16) . . . . ?
C2 C17 C18 C19 61.06(17) . . . . ?
C22 C17 C18 C19 -174.81(13) . . . . ?
C18 C17 O1 B1 163.65(12) . . . . ?
C2 C17 O1 B1 43.38(17) . . . . ?
C22 C17 O1 B1 -78.85(16) . . . . ?
C7 C8 O2 B1 -21.2(2) . . . . ?
C9 C8 O2 B1 162.81(13) . . . . ?
C1 N1 N2 C7 -172.44(12) . . . . ?
B1 N1 N2 C7 8.90(19) . . . . ?
C8 C7 N2 N1 13.1(2) . . . . ?
C16 C7 N2 N1 -176.39(12) . . . . ?
C17 O1 B1 F1 70.40(17) . . . . ?
C17 O1 B1 O2 -166.46(11) . . . . ?
C17 O1 B1 N1 -49.04(17) . . . . ?
C8 O2 B1 O1 156.66(12) . . . . ?
C8 O2 B1 F1 -75.57(16) . . . . ?
C8 O2 B1 N1 37.17(17) . . . . ?
N2 N1 B1 O1 -151.76(13) . . . . ?
C1 N1 B1 O1 29.62(18) . . . . ?
N2 N1 B1 F1 82.14(16) . . . . ?
C1 N1 B1 F1 -96.48(15) . . . . ?
N2 N1 B1 O2 -32.85(18) . . . . ?
C1 N1 B1 O2 148.53(12) . . . . ?
N2 N1 C1 C6 -6.0(2) . . . . ?
B1 N1 C1 C6 172.74(14) . . . . ?
N2 N1 C1 C2 173.44(13) . . . . ?
B1 N1 C1 C2 -7.9(2) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
N1 C1 C2 C3 -178.53(13) . . . . ?
C6 C1 C2 C17 -178.76(14) . . . . ?
N1 C1 C2 C17 1.8(2) . . . . ?
O1 C17 C2 C1 -17.24(19) . . . . ?
C18 C17 C2 C1 -133.40(14) . . . . ?
C22 C17 C2 C1 103.06(16) . . . . ?
O1 C17 C2 C3 163.15(13) . . . . ?
C18 C17 C2 C3 47.00(18) . . . . ?
C22 C17 C2 C3 -76.54(17) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C17 C2 C3 C4 178.43(14) . . . . ?
O2 C8 C9 C10 179.23(14) . . . . ?
C7 C8 C9 C10 3.2(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C6 C5 C4 C3 0.4(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
N1 C1 C6 C5 179.47(14) . . . . ?
C8 C9 C10 C11 -1.8(2) . . . . ?
C12 C11 C10 C9 -178.58(15) . . . . ?
C16 C11 C10 C9 -1.2(2) . . . . ?
C14 C13 C12 C11 -0.7(2) . . . . ?
C16 C11 C12 C13 -0.6(2) . . . . ?
C10 C11 C12 C13 176.84(15) . . . . ?
C12 C13 C14 C15 1.1(2) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C14 C15 C16 C11 -1.1(2) . . . . ?
C14 C15 C16 C7 -179.73(14) . . . . ?
C12 C11 C16 C15 1.5(2) . . . . ?
C10 C11 C16 C15 -176.05(14) . . . . ?
C12 C11 C16 C7 -179.85(13) . . . . ?
C10 C11 C16 C7 2.6(2) . . . . ?
N2 C7 C16 C15 6.6(2) . . . . ?
C8 C7 C16 C15 177.38(14) . . . . ?
N2 C7 C16 C11 -172.01(12) . . . . ?
C8 C7 C16 C11 -1.3(2) . . . . ?
C17 C18 C19 C20 178.21(14) . . . . ?
C21 C20 C19 C18 -176.54(16) . . . . ?
O1 C17 C22 C23 -172.53(13) . . . . ?
C18 C17 C22 C23 -58.71(18) . . . . ?
C2 C17 C22 C23 65.48(17) . . . . ?
C17 C22 C23 C24 173.51(14) . . . . ?
C25 C24 C23 C22 178.16(17) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.042


_exptl_crystal_preparation       Luminescent
