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

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

data_proffuruta
_database_code_depnum_ccdc_archive 'CCDC 2320994'
loop_
_audit_author_name
_audit_author_address
'Soji Shimizu'
;Kyushu University
Japan
;
_audit_update_record             
;
2023-12-21 deposited with the CCDC.	2024-03-01 downloaded from the CCDC.
;
_audit_creation_date             2023-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        'axially-fluoro-substituted azabora[6]helicene'
_chemical_formula_moiety         'C27 H15 B F N5'
_chemical_formula_sum            'C27 H15 B F N5'
_chemical_formula_weight         439.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H15 B1 F1 N5'
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'

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

_cell_length_a                   8.0536(5)
_cell_length_b                   8.9238(5)
_cell_length_c                   15.0934(9)
_cell_angle_alpha                79.306(5)
_cell_angle_beta                 85.035(5)
_cell_angle_gamma                65.599(5)
_cell_volume                     970.63(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9636
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.7670
_cell_measurement_theta_min      2.5090
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19008
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.990
_diffrn_reflns_theta_min         2.541
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  75.00   0.50    4.00    --  -15.00  45.00   0.00  360
  2  ω   -105.00  75.00   0.50    4.00    --  -15.00  45.00  90.00  360
  3  ω   -105.00  75.00   0.50    4.00    --  -15.00  45.00 180.00  360
  4  ω   -105.00  75.00   0.50    4.00    --  -15.00  45.00 270.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0695571000
_diffrn_orient_matrix_UB_12      -0.0769208000
_diffrn_orient_matrix_UB_13      -0.0083601000
_diffrn_orient_matrix_UB_21      0.0583097000
_diffrn_orient_matrix_UB_22      0.0075259000
_diffrn_orient_matrix_UB_23      0.0299270000
_diffrn_orient_matrix_UB_31      -0.0334068000
_diffrn_orient_matrix_UB_32      -0.0431037000
_diffrn_orient_matrix_UB_33      0.0363589000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3200
_reflns_number_total             4687
_reflns_odcompleteness_completeness 90.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.77
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4687
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+0.0520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1277
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C25(H25), C6(H6), C23(H23), C2(H2), C7(H7), C24(H24), C19(H19),
 C4(H4), C3(H3), C13(H13), C15(H15), C21(H21), C14(H14), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.23609(13) 0.83699(12) 0.21100(7) 0.0256(3) Uani 1 1 d . . . . .
N5 N 0.36186(19) 0.68068(17) 0.35304(9) 0.0204(3) Uani 1 1 d . . . . .
N2 N 0.7443(2) 0.62540(18) 0.14698(10) 0.0220(3) Uani 1 1 d . . . . .
N1 N 0.48127(19) 0.57217(17) 0.20069(9) 0.0198(3) Uani 1 1 d . . . . .
N4 N 0.3739(2) 0.93754(18) 0.36938(10) 0.0233(4) Uani 1 1 d . . . . .
N3 N 0.53914(19) 0.79770(17) 0.24794(10) 0.0207(3) Uani 1 1 d . . . . .
C11 C 0.6417(2) 0.5434(2) 0.15173(11) 0.0205(4) Uani 1 1 d . . . . .
C10 C 0.5186(2) 0.3743(2) 0.11606(11) 0.0200(4) Uani 1 1 d . . . . .
C26 C 0.3157(2) 0.5593(2) 0.41070(12) 0.0200(4) Uani 1 1 d . . . . .
C18 C 0.2407(2) 0.7818(2) 0.48507(12) 0.0214(4) Uani 1 1 d . . . . .
C9 C 0.6733(2) 0.4092(2) 0.10024(11) 0.0204(4) Uani 1 1 d . . . . .
C27 C 0.2420(2) 0.6237(2) 0.49016(12) 0.0209(4) Uani 1 1 d . . . . .
C1 C 0.3980(2) 0.4744(2) 0.17502(11) 0.0204(4) Uani 1 1 d . . . . .
C17 C 0.3257(2) 0.8132(2) 0.39767(12) 0.0218(4) Uani 1 1 d . . . . .
C5 C 0.4821(2) 0.2647(2) 0.07399(12) 0.0215(4) Uani 1 1 d . . . . .
C8 C 0.8049(2) 0.3287(2) 0.04040(12) 0.0236(4) Uani 1 1 d . . . . .
H8 H 0.9095 0.3493 0.0283 0.028 Uiso 1 1 calc R U . . .
C25 C 0.3353(2) 0.4018(2) 0.40498(12) 0.0231(4) Uani 1 1 d . . . . .
H25 H 0.3857 0.3547 0.3538 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6196(2) 0.1826(2) 0.01361(12) 0.0241(4) Uani 1 1 d . . . . .
H6 H 0.6055 0.1064 -0.0162 0.029 Uiso 1 1 calc R U . . .
C23 C 0.2011(2) 0.3762(2) 0.55684(12) 0.0255(4) Uani 1 1 d . . . . .
H23 H 0.1619 0.3141 0.6035 0.031 Uiso 1 1 calc R U . . .
C12 C 0.6923(2) 0.7564(2) 0.19357(12) 0.0213(4) Uani 1 1 d . . . . .
C16 C 0.4997(2) 0.9189(2) 0.30111(12) 0.0220(4) Uani 1 1 d . . . . .
C2 C 0.2326(2) 0.4676(2) 0.19384(12) 0.0224(4) Uani 1 1 d . . . . .
H2 H 0.1482 0.5346 0.2314 0.027 Uiso 1 1 calc R U . . .
C7 C 0.7744(2) 0.2140(2) -0.00164(12) 0.0247(4) Uani 1 1 d . . . . .
H7 H 0.8626 0.1569 -0.0414 0.030 Uiso 1 1 calc R U . . .
C24 C 0.2764(2) 0.3121(2) 0.47947(12) 0.0246(4) Uani 1 1 d . . . . .
H24 H 0.2893 0.2050 0.4758 0.030 Uiso 1 1 calc R U . . .
C19 C 0.1739(2) 0.8651(2) 0.55715(12) 0.0268(4) Uani 1 1 d . . . . .
H19 H 0.1723 0.9702 0.5563 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3114(3) 0.2553(2) 0.09595(12) 0.0249(4) Uani 1 1 d . . . . .
H4 H 0.2794 0.1828 0.0714 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1943(3) 0.3532(2) 0.15341(13) 0.0264(4) Uani 1 1 d . . . . .
H3 H 0.0833 0.3448 0.1669 0.032 Uiso 1 1 calc R U . . .
C13 C 0.7984(3) 0.8467(2) 0.18607(13) 0.0261(4) Uani 1 1 d . . . . .
H13 H 0.9023 0.8187 0.1496 0.031 Uiso 1 1 calc R U . . .
C22 C 0.1839(2) 0.5387(2) 0.56450(12) 0.0237(4) Uani 1 1 d . . . . .
C15 C 0.6026(3) 1.0137(2) 0.29018(13) 0.0266(4) Uani 1 1 d . . . . .
H15 H 0.5713 1.1017 0.3219 0.032 Uiso 1 1 calc R U . . .
C21 C 0.1133(3) 0.6275(2) 0.63690(13) 0.0292(5) Uani 1 1 d . . . . .
H21 H 0.0697 0.5792 0.6883 0.035 Uiso 1 1 calc R U . . .
C14 C 0.7509(3) 0.9774(2) 0.23238(13) 0.0281(4) Uani 1 1 d . . . . .
H14 H 0.8189 1.0416 0.2247 0.034 Uiso 1 1 calc R U . . .
C20 C 0.1081(3) 0.7851(2) 0.63234(13) 0.0306(5) Uani 1 1 d . . . . .
H20 H 0.0591 0.8410 0.6809 0.037 Uiso 1 1 calc R U . . .
B1 B 0.3989(3) 0.7173(2) 0.25165(14) 0.0216(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.405(2) . ?
N5 C26 1.413(2) . ?
N5 C17 1.384(2) . ?
N5 B1 1.534(2) . ?
N2 C11 1.302(2) . ?
N2 C12 1.373(2) . ?
N1 C11 1.383(2) . ?
N1 C1 1.419(2) . ?
N1 B1 1.510(2) . ?
N4 C17 1.310(2) . ?
N4 C16 1.363(2) . ?
N3 C12 1.376(2) . ?
N3 C16 1.381(2) . ?
N3 B1 1.561(3) . ?
C11 C9 1.470(2) . ?
C10 C9 1.396(2) . ?
C10 C1 1.401(2) . ?
C10 C5 1.395(2) . ?
C26 C27 1.404(2) . ?
C26 C25 1.366(2) . ?
C18 C27 1.394(2) . ?
C18 C17 1.467(2) . ?
C18 C19 1.376(2) . ?
C9 C8 1.379(2) . ?
C27 C22 1.392(3) . ?
C1 C2 1.362(2) . ?
C5 C6 1.413(2) . ?
C5 C4 1.419(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.410(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.420(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.377(3) . ?
C23 C22 1.424(3) . ?
C12 C13 1.382(3) . ?
C16 C15 1.392(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.426(2) . ?
C7 H7 0.9300 . ?
C24 H24 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.409(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.365(3) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.373(3) . ?
C22 C21 1.410(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.377(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.379(3) . ?
C14 H14 0.9300 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 N5 B1 135.60(15) . . ?
C17 N5 C26 108.69(14) . . ?
C17 N5 B1 113.99(15) . . ?
C11 N2 C12 118.91(16) . . ?
C11 N1 C1 108.17(14) . . ?
C11 N1 B1 121.22(15) . . ?
C1 N1 B1 128.81(14) . . ?
C17 N4 C16 117.15(15) . . ?
C12 N3 C16 120.37(16) . . ?
C12 N3 B1 123.25(15) . . ?
C16 N3 B1 116.36(15) . . ?
N2 C11 N1 126.78(16) . . ?
N2 C11 C9 124.67(16) . . ?
N1 C11 C9 108.45(15) . . ?
C9 C10 C1 110.36(15) . . ?
C5 C10 C9 124.99(16) . . ?
C5 C10 C1 124.49(16) . . ?
C27 C26 N5 107.22(15) . . ?
C25 C26 N5 133.93(16) . . ?
C25 C26 C27 118.79(16) . . ?
C27 C18 C17 105.17(15) . . ?
C19 C18 C27 119.04(17) . . ?
C19 C18 C17 135.72(17) . . ?
C10 C9 C11 105.12(15) . . ?
C8 C9 C11 135.46(17) . . ?
C8 C9 C10 119.21(16) . . ?
C18 C27 C26 110.48(16) . . ?
C22 C27 C26 124.49(16) . . ?
C22 C27 C18 125.00(16) . . ?
C10 C1 N1 107.53(15) . . ?
C2 C1 N1 133.07(16) . . ?
C2 C1 C10 119.34(16) . . ?
N5 C17 C18 108.26(15) . . ?
N4 C17 N5 125.25(17) . . ?
N4 C17 C18 126.25(16) . . ?
C10 C5 C6 114.75(17) . . ?
C10 C5 C4 115.69(16) . . ?
C6 C5 C4 129.53(17) . . ?
C9 C8 H8 121.4 . . ?
C9 C8 C7 117.24(17) . . ?
C7 C8 H8 121.4 . . ?
C26 C25 H25 120.9 . . ?
C26 C25 C24 118.13(17) . . ?
C24 C25 H25 120.9 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.88(17) . . ?
C7 C6 H6 119.6 . . ?
C24 C23 H23 120.4 . . ?
C24 C23 C22 119.25(17) . . ?
C22 C23 H23 120.4 . . ?
N2 C12 N3 121.47(16) . . ?
N2 C12 C13 118.78(17) . . ?
N3 C12 C13 119.75(17) . . ?
N4 C16 N3 121.64(16) . . ?
N4 C16 C15 119.03(16) . . ?
N3 C16 C15 119.06(17) . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.11(16) . . ?
C3 C2 H2 121.4 . . ?
C8 C7 H7 118.6 . . ?
C6 C7 C8 122.90(17) . . ?
C6 C7 H7 118.6 . . ?
C25 C24 H24 118.4 . . ?
C23 C24 C25 123.16(17) . . ?
C23 C24 H24 118.4 . . ?
C18 C19 H19 121.3 . . ?
C18 C19 C20 117.45(17) . . ?
C20 C19 H19 121.3 . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.60(17) . . ?
C3 C4 H4 120.2 . . ?
C2 C3 H3 118.1 . . ?
C4 C3 C2 123.73(18) . . ?
C4 C3 H3 118.1 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.17(18) . . ?
C14 C13 H13 119.9 . . ?
C27 C22 C23 116.16(16) . . ?
C27 C22 C21 114.96(17) . . ?
C21 C22 C23 128.87(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.06(17) . . ?
C14 C15 H15 120.0 . . ?
C22 C21 H21 119.6 . . ?
C20 C21 C22 120.74(18) . . ?
C20 C21 H21 119.6 . . ?
C13 C14 C15 120.09(18) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C19 C20 H20 118.6 . . ?
C21 C20 C19 122.75(18) . . ?
C21 C20 H20 118.6 . . ?
F1 B1 N5 108.07(15) . . ?
F1 B1 N1 110.39(15) . . ?
F1 B1 N3 109.10(15) . . ?
N5 B1 N3 103.04(14) . . ?
N1 B1 N5 118.18(15) . . ?
N1 B1 N3 107.58(15) . . ?

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
N5 C26 C27 C18 -0.33(18) . . . . ?
N5 C26 C27 C22 -178.43(15) . . . . ?
N5 C26 C25 C24 177.92(17) . . . . ?
N2 C11 C9 C10 -171.76(16) . . . . ?
N2 C11 C9 C8 2.7(3) . . . . ?
N2 C12 C13 C14 -179.46(16) . . . . ?
N1 C11 C9 C10 4.85(18) . . . . ?
N1 C11 C9 C8 179.31(18) . . . . ?
N1 C1 C2 C3 178.67(18) . . . . ?
N4 C16 C15 C14 168.82(16) . . . . ?
N3 C12 C13 C14 -0.3(3) . . . . ?
N3 C16 C15 C14 -5.3(3) . . . . ?
C11 N2 C12 N3 2.9(2) . . . . ?
C11 N2 C12 C13 -177.92(16) . . . . ?
C11 N1 C1 C10 5.43(18) . . . . ?
C11 N1 C1 C2 -171.77(18) . . . . ?
C11 N1 B1 F1 110.94(17) . . . . ?
C11 N1 B1 N5 -123.99(17) . . . . ?
C11 N1 B1 N3 -8.0(2) . . . . ?
C11 C9 C8 C7 -173.97(18) . . . . ?
C10 C9 C8 C7 -0.1(2) . . . . ?
C10 C1 C2 C3 1.7(2) . . . . ?
C10 C5 C6 C7 -0.9(2) . . . . ?
C10 C5 C4 C3 1.4(2) . . . . ?
C26 N5 C17 N4 170.53(16) . . . . ?
C26 N5 C17 C18 -4.15(18) . . . . ?
C26 N5 B1 F1 95.4(2) . . . . ?
C26 N5 B1 N1 -30.8(3) . . . . ?
C26 N5 B1 N3 -149.24(17) . . . . ?
C26 C27 C22 C23 -0.5(2) . . . . ?
C26 C27 C22 C21 -179.62(15) . . . . ?
C26 C25 C24 C23 -0.1(3) . . . . ?
C18 C27 C22 C23 -178.38(16) . . . . ?
C18 C27 C22 C21 2.5(2) . . . . ?
C18 C19 C20 C21 1.9(3) . . . . ?
C9 C10 C1 N1 -2.33(19) . . . . ?
C9 C10 C1 C2 175.32(15) . . . . ?
C9 C10 C5 C6 2.0(3) . . . . ?
C9 C10 C5 C4 -176.30(16) . . . . ?
C9 C8 C7 C6 1.1(3) . . . . ?
C27 C26 C25 C24 1.2(2) . . . . ?
C27 C18 C17 N5 3.85(18) . . . . ?
C27 C18 C17 N4 -170.76(16) . . . . ?
C27 C18 C19 C20 -0.7(2) . . . . ?
C27 C22 C21 C20 -1.3(2) . . . . ?
C1 N1 C11 N2 170.16(16) . . . . ?
C1 N1 C11 C9 -6.35(18) . . . . ?
C1 N1 B1 F1 -51.9(2) . . . . ?
C1 N1 B1 N5 73.2(2) . . . . ?
C1 N1 B1 N3 -170.79(15) . . . . ?
C1 C10 C9 C11 -1.47(19) . . . . ?
C1 C10 C9 C8 -177.02(15) . . . . ?
C1 C10 C5 C6 176.88(16) . . . . ?
C1 C10 C5 C4 -1.5(3) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
C17 N5 C26 C27 2.83(18) . . . . ?
C17 N5 C26 C25 -174.15(18) . . . . ?
C17 N5 B1 F1 -67.54(19) . . . . ?
C17 N5 B1 N1 166.27(14) . . . . ?
C17 N5 B1 N3 47.85(18) . . . . ?
C17 N4 C16 N3 16.8(2) . . . . ?
C17 N4 C16 C15 -157.17(16) . . . . ?
C17 C18 C27 C26 -2.12(18) . . . . ?
C17 C18 C27 C22 175.97(15) . . . . ?
C17 C18 C19 C20 -177.32(18) . . . . ?
C5 C10 C9 C11 173.99(16) . . . . ?
C5 C10 C9 C8 -1.6(3) . . . . ?
C5 C10 C1 N1 -177.81(15) . . . . ?
C5 C10 C1 C2 -0.2(3) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C25 C26 C27 C18 177.19(15) . . . . ?
C25 C26 C27 C22 -0.9(2) . . . . ?
C6 C5 C4 C3 -176.61(18) . . . . ?
C23 C22 C21 C20 179.78(18) . . . . ?
C12 N2 C11 N1 -0.8(3) . . . . ?
C12 N2 C11 C9 175.19(15) . . . . ?
C12 N3 C16 N4 -165.48(15) . . . . ?
C12 N3 C16 C15 8.5(2) . . . . ?
C12 N3 B1 F1 -109.50(17) . . . . ?
C12 N3 B1 N5 135.84(15) . . . . ?
C12 N3 B1 N1 10.3(2) . . . . ?
C12 C13 C14 C15 3.4(3) . . . . ?
C16 N4 C17 N5 -14.0(2) . . . . ?
C16 N4 C17 C18 159.75(16) . . . . ?
C16 N3 C12 N2 173.45(15) . . . . ?
C16 N3 C12 C13 -5.7(2) . . . . ?
C16 N3 B1 F1 68.72(19) . . . . ?
C16 N3 B1 N5 -45.93(18) . . . . ?
C16 N3 B1 N1 -171.52(14) . . . . ?
C16 C15 C14 C13 -0.6(3) . . . . ?
C24 C23 C22 C27 1.6(2) . . . . ?
C24 C23 C22 C21 -179.43(17) . . . . ?
C19 C18 C27 C26 -179.66(15) . . . . ?
C19 C18 C27 C22 -1.6(3) . . . . ?
C19 C18 C17 N5 -179.22(18) . . . . ?
C19 C18 C17 N4 6.2(3) . . . . ?
C4 C5 C6 C7 177.12(17) . . . . ?
C22 C23 C24 C25 -1.4(3) . . . . ?
C22 C21 C20 C19 -0.9(3) . . . . ?
B1 N5 C26 C27 -160.70(17) . . . . ?
B1 N5 C26 C25 22.3(3) . . . . ?
B1 N5 C17 N4 -22.0(2) . . . . ?
B1 N5 C17 C18 163.31(14) . . . . ?
B1 N1 C11 N2 4.2(3) . . . . ?
B1 N1 C11 C9 -172.32(14) . . . . ?
B1 N1 C1 C10 169.99(16) . . . . ?
B1 N1 C1 C2 -7.2(3) . . . . ?
B1 N3 C12 N2 -8.4(2) . . . . ?
B1 N3 C12 C13 172.43(16) . . . . ?
B1 N3 C16 N4 16.2(2) . . . . ?
B1 N3 C16 C15 -169.83(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.305
_oxdiff_exptl_absorpt_empirical_full_min 0.542
####################################################################### 
# 
# 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_shimizu_autored
_database_code_depnum_ccdc_archive 'CCDC 2320995'
loop_
_audit_author_name
_audit_author_address
'Soji Shimizu'
;Kyushu University
Japan
;
_audit_update_record             
;
2023-12-21 deposited with the CCDC.	2024-03-01 downloaded from the CCDC.
;
_audit_creation_date             2023-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        'axially-phenyl-substituted azabora[6]helicene'
_chemical_formula_moiety         'C H2 Cl2, C33 H20 B N5'
_chemical_formula_sum            'C34 H22 B Cl2 N5'
_chemical_formula_weight         582.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C33 H20 B1 N5'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.3419(4)
_cell_length_b                   10.0645(5)
_cell_length_c                   14.7904(6)
_cell_angle_alpha                91.141(4)
_cell_angle_beta                 105.751(4)
_cell_angle_gamma                90.019(4)
_cell_volume                     1338.11(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12630
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.7140
_cell_measurement_theta_min      2.2450
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25738
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_min         2.024
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 7.111
_diffrn_detector_type            'Rigaku Saturn724+ area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

 # Type Start End Width tₑₓₚ ω θ κ φ Frames
#--------------------------------------------------------------------------
 1 ω -105.00 75.00 0.50 1.00 -- -15.00 45.00 0.00 360
 2 ω -105.00 75.00 0.50 1.00 -- -15.00 45.00 90.00 360
 3 ω -105.00 75.00 0.50 1.00 -- -15.00 45.00 180.00 360
 4 ω -105.00 75.00 0.50 1.00 -- -15.00 45.00 270.00 360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0685389000
_diffrn_orient_matrix_UB_12      0.0205901000
_diffrn_orient_matrix_UB_13      0.0075198000
_diffrn_orient_matrix_UB_21      0.0225144000
_diffrn_orient_matrix_UB_22      0.0673781000
_diffrn_orient_matrix_UB_23      0.0004492000
_diffrn_orient_matrix_UB_31      -0.0319256000
_diffrn_orient_matrix_UB_32      0.0022754000
_diffrn_orient_matrix_UB_33      -0.0492661000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'MicroMax 007'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5018
_reflns_number_total             6621
_reflns_odcompleteness_completeness 87.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.67
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0691P)²+0.4965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1447
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C4(H4), C15(H15), C2(H2), C24(H24), C3(H3), C14(H14), C13(H13),
 C33(H33), C8(H8), C6(H6), C29(H29), C19(H19), C23(H23), C21(H21), C7(H7),
 C32(H32), C30(H30), C20(H20), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Cl1 Cl -0.24735(6) 0.04464(5) 0.20706(4) 0.02984(16) Uani 1 1 d . . . . .
Cl2 Cl -0.01568(7) 0.04869(6) 0.38480(4) 0.03772(18) Uani 1 1 d . . . . .
N3 N 0.15291(17) 0.55797(16) 0.27642(11) 0.0153(3) Uani 1 1 d . . . . .
N5 N 0.35771(17) 0.42598(16) 0.36794(11) 0.0152(3) Uani 1 1 d . . . . .
N4 N 0.11436(18) 0.40627(16) 0.39095(12) 0.0173(4) Uani 1 1 d . . . . .
N1 N 0.37500(17) 0.54485(15) 0.21354(11) 0.0154(3) Uani 1 1 d . . . . .
N2 N 0.21082(18) 0.73323(16) 0.18466(12) 0.0182(4) Uani 1 1 d . . . . .
C10 C 0.5296(2) 0.61109(19) 0.12683(13) 0.0160(4) Uani 1 1 d . . . . .
C1 C 0.4940(2) 0.50405(19) 0.17693(13) 0.0162(4) Uani 1 1 d . . . . .
C5 C 0.6380(2) 0.6087(2) 0.07780(14) 0.0187(4) Uani 1 1 d . . . . .
C28 C 0.2123(2) 0.3306(2) 0.20423(14) 0.0178(4) Uani 1 1 d . . . . .
C16 C 0.0686(2) 0.51190(19) 0.33269(14) 0.0173(4) Uani 1 1 d . . . . .
C11 C 0.3308(2) 0.66975(19) 0.17974(14) 0.0171(4) Uani 1 1 d . . . . .
C9 C 0.4339(2) 0.7171(2) 0.12791(14) 0.0184(4) Uani 1 1 d . . . . .
C25 C 0.6397(2) 0.39791(19) 0.40387(13) 0.0171(4) Uani 1 1 d . . . . .
H25 H 0.6557 0.4577 0.3604 0.020 Uiso 1 1 calc R U . . .
C26 C 0.4999(2) 0.37518(19) 0.41340(13) 0.0160(4) Uani 1 1 d . . . . .
C18 C 0.3330(2) 0.28235(19) 0.48430(14) 0.0184(4) Uani 1 1 d . . . . .
C17 C 0.2561(2) 0.37470(19) 0.41126(13) 0.0160(4) Uani 1 1 d . . . . .
C4 C 0.7159(2) 0.4875(2) 0.07999(14) 0.0202(4) Uani 1 1 d . . . . .
H4 H 0.7901 0.4793 0.0491 0.024 Uiso 1 1 calc R U . . .
C27 C 0.4822(2) 0.28736(19) 0.48270(13) 0.0173(4) Uani 1 1 d . . . . .
C12 C 0.1186(2) 0.67658(19) 0.23100(14) 0.0176(4) Uani 1 1 d . . . . .
C15 C -0.0617(2) 0.5783(2) 0.33477(15) 0.0199(4) Uani 1 1 d . . . . .
H15 H -0.1207 0.5465 0.3712 0.024 Uiso 1 1 calc R U . . .
C2 C 0.5691(2) 0.3866(2) 0.17739(14) 0.0184(4) Uani 1 1 d . . . . .
H2 H 0.5479 0.3130 0.2086 0.022 Uiso 1 1 calc R U . . .
C24 C 0.7600(2) 0.3262(2) 0.46321(14) 0.0195(4) Uani 1 1 d . . . . .
H24 H 0.8553 0.3404 0.4572 0.023 Uiso 1 1 calc R U . . .
C3 C 0.6812(2) 0.3820(2) 0.12803(14) 0.0210(4) Uani 1 1 d . . . . .
H3 H 0.7335 0.3033 0.1284 0.025 Uiso 1 1 calc R U . . .
C22 C 0.5978(2) 0.2155(2) 0.54129(14) 0.0201(4) Uani 1 1 d . . . . .
C14 C -0.1029(2) 0.6910(2) 0.28296(15) 0.0216(4) Uani 1 1 d . . . . .
H14 H -0.1920 0.7328 0.2821 0.026 Uiso 1 1 calc R U . . .
C13 C -0.0122(2) 0.7421(2) 0.23228(14) 0.0203(4) Uani 1 1 d . . . . .
H13 H -0.0383 0.8200 0.1991 0.024 Uiso 1 1 calc R U . . .
C33 C 0.0919(2) 0.3393(2) 0.12409(14) 0.0227(5) Uani 1 1 d . . . . .
H33 H 0.0558 0.4226 0.1033 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4460(3) 0.8297(2) 0.07950(16) 0.0267(5) Uani 1 1 d . . . . .
H8 H 0.3828 0.9015 0.0783 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6509(2) 0.7270(2) 0.02996(15) 0.0239(5) Uani 1 1 d . . . . .
H6 H 0.7226 0.7332 -0.0028 0.029 Uiso 1 1 calc R U . . .
C29 C 0.2637(2) 0.2026(2) 0.23092(15) 0.0238(5) Uani 1 1 d . . . . .
H29 H 0.3442 0.1932 0.2835 0.029 Uiso 1 1 calc R U . . .
C19 C 0.2932(2) 0.2005(2) 0.54715(15) 0.0233(5) Uani 1 1 d . . . . .
H19 H 0.1953 0.1955 0.5504 0.028 Uiso 1 1 calc R U . . .
C23 C 0.7419(2) 0.2371(2) 0.52885(14) 0.0215(4) Uani 1 1 d . . . . .
H23 H 0.8233 0.1914 0.5649 0.026 Uiso 1 1 calc R U . . .
C21 C 0.5536(3) 0.1306(2) 0.60476(15) 0.0273(5) Uani 1 1 d . . . . .
H21 H 0.6241 0.0788 0.6454 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5578(3) 0.8329(2) 0.03157(17) 0.0305(5) Uani 1 1 d . . . . .
H7 H 0.5691 0.9093 -0.0002 0.037 Uiso 1 1 calc R U . . .
C32 C 0.0243(2) 0.2255(3) 0.07433(16) 0.0309(5) Uani 1 1 d . . . . .
H32 H -0.0559 0.2334 0.0213 0.037 Uiso 1 1 calc R U . . .
C30 C 0.1987(3) 0.0893(2) 0.18178(16) 0.0324(6) Uani 1 1 d . . . . .
H30 H 0.2365 0.0059 0.2007 0.039 Uiso 1 1 calc R U . . .
C34 C -0.1094(3) 0.1424(2) 0.28710(15) 0.0264(5) Uani 1 1 d . . . . .
H34A H -0.0383 0.1748 0.2555 0.032 Uiso 1 1 calc R U . . .
H34B H -0.1557 0.2187 0.3084 0.032 Uiso 1 1 calc R U . . .
C20 C 0.4065(3) 0.1245(2) 0.60659(16) 0.0289(5) Uani 1 1 d . . . . .
H20 H 0.3810 0.0679 0.6488 0.035 Uiso 1 1 calc R U . . .
C31 C 0.0778(3) 0.1013(2) 0.10477(16) 0.0343(6) Uani 1 1 d . . . . .
H31 H 0.0318 0.0255 0.0730 0.041 Uiso 1 1 calc R U . . .
B1 B 0.2829(2) 0.4634(2) 0.26430(15) 0.0149(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
Cl1 C34 1.776(2) . ?
Cl2 C34 1.764(2) . ?
N3 C16 1.378(2) . ?
N3 C12 1.376(2) . ?
N3 B1 1.589(3) . ?
N5 C26 1.417(2) . ?
N5 C17 1.386(2) . ?
N5 B1 1.556(3) . ?
N4 C16 1.376(3) . ?
N4 C17 1.316(2) . ?
N1 C1 1.420(2) . ?
N1 C11 1.383(2) . ?
N1 B1 1.533(3) . ?
N2 C11 1.308(3) . ?
N2 C12 1.368(3) . ?
C10 C1 1.409(3) . ?
C10 C5 1.396(3) . ?
C10 C9 1.395(3) . ?
C1 C2 1.374(3) . ?
C5 C4 1.417(3) . ?
C5 C6 1.418(3) . ?
C28 C33 1.399(3) . ?
C28 C29 1.402(3) . ?
C28 B1 1.626(3) . ?
C16 C15 1.396(3) . ?
C11 C9 1.469(3) . ?
C9 C8 1.374(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.371(3) . ?
C25 C24 1.430(3) . ?
C26 C27 1.410(3) . ?
C18 C17 1.472(3) . ?
C18 C27 1.401(3) . ?
C18 C19 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.376(3) . ?
C27 C22 1.399(3) . ?
C12 C13 1.394(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.377(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.430(3) . ?
C24 H24 0.9300 . ?
C24 C23 1.378(3) . ?
C3 H3 0.9300 . ?
C22 C23 1.424(3) . ?
C22 C21 1.423(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.379(3) . ?
C13 H13 0.9300 . ?
C33 H33 0.9300 . ?
C33 C32 1.402(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.414(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.387(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.415(3) . ?
C23 H23 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.382(3) . ?
C7 H7 0.9300 . ?
C32 H32 0.9300 . ?
C32 C31 1.384(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.376(4) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C20 H20 0.9300 . ?
C31 H31 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N3 B1 116.10(16) . . ?
C12 N3 C16 120.31(16) . . ?
C12 N3 B1 123.52(16) . . ?
C26 N5 B1 132.60(16) . . ?
C17 N5 C26 108.11(15) . . ?
C17 N5 B1 111.98(15) . . ?
C17 N4 C16 117.32(16) . . ?
C1 N1 B1 129.41(16) . . ?
C11 N1 C1 107.96(15) . . ?
C11 N1 B1 121.54(16) . . ?
C11 N2 C12 119.00(17) . . ?
C5 C10 C1 125.16(18) . . ?
C9 C10 C1 110.03(17) . . ?
C9 C10 C5 124.68(18) . . ?
C10 C1 N1 107.67(16) . . ?
C2 C1 N1 133.82(18) . . ?
C2 C1 C10 118.41(18) . . ?
C10 C5 C4 115.76(18) . . ?
C10 C5 C6 115.12(19) . . ?
C4 C5 C6 129.08(19) . . ?
C33 C28 C29 116.55(19) . . ?
C33 C28 B1 120.77(18) . . ?
C29 C28 B1 122.64(18) . . ?
N3 C16 C15 119.42(18) . . ?
N4 C16 N3 121.33(17) . . ?
N4 C16 C15 119.15(18) . . ?
N1 C11 C9 108.74(16) . . ?
N2 C11 N1 127.06(18) . . ?
N2 C11 C9 123.97(18) . . ?
C10 C9 C11 105.27(17) . . ?
C8 C9 C10 119.30(19) . . ?
C8 C9 C11 135.23(19) . . ?
C26 C25 H25 121.2 . . ?
C26 C25 C24 117.51(18) . . ?
C24 C25 H25 121.2 . . ?
C25 C26 N5 133.26(18) . . ?
C25 C26 C27 119.06(18) . . ?
C27 C26 N5 107.65(16) . . ?
C27 C18 C17 104.73(16) . . ?
C19 C18 C17 136.25(19) . . ?
C19 C18 C27 119.02(19) . . ?
N5 C17 C18 109.04(16) . . ?
N4 C17 N5 124.99(18) . . ?
N4 C17 C18 125.96(17) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.58(19) . . ?
C3 C4 H4 120.2 . . ?
C18 C27 C26 110.40(17) . . ?
C22 C27 C26 124.54(18) . . ?
C22 C27 C18 125.06(18) . . ?
N3 C12 C13 119.82(18) . . ?
N2 C12 N3 121.59(17) . . ?
N2 C12 C13 118.59(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 C16 120.05(19) . . ?
C14 C15 H15 120.0 . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.43(19) . . ?
C3 C2 H2 121.3 . . ?
C25 C24 H24 118.3 . . ?
C23 C24 C25 123.33(19) . . ?
C23 C24 H24 118.3 . . ?
C4 C3 C2 123.65(19) . . ?
C4 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
C27 C22 C23 115.80(18) . . ?
C27 C22 C21 114.82(19) . . ?
C21 C22 C23 129.38(19) . . ?
C15 C14 H14 119.9 . . ?
C15 C14 C13 120.14(19) . . ?
C13 C14 H14 119.9 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.75(19) . . ?
C14 C13 H13 120.1 . . ?
C28 C33 H33 119.2 . . ?
C28 C33 C32 121.6(2) . . ?
C32 C33 H33 119.2 . . ?
C9 C8 H8 121.2 . . ?
C9 C8 C7 117.7(2) . . ?
C7 C8 H8 121.2 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
C28 C29 H29 118.8 . . ?
C30 C29 C28 122.4(2) . . ?
C30 C29 H29 118.8 . . ?
C18 C19 H19 121.2 . . ?
C18 C19 C20 117.6(2) . . ?
C20 C19 H19 121.2 . . ?
C24 C23 C22 119.70(19) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C22 C21 H21 119.7 . . ?
C20 C21 C22 120.5(2) . . ?
C20 C21 H21 119.7 . . ?
C8 C7 H7 118.7 . . ?
C6 C7 C8 122.6(2) . . ?
C6 C7 H7 118.7 . . ?
C33 C32 H32 120.3 . . ?
C31 C32 C33 119.4(2) . . ?
C31 C32 H32 120.3 . . ?
C29 C30 H30 120.2 . . ?
C31 C30 C29 119.5(2) . . ?
C31 C30 H30 120.2 . . ?
Cl1 C34 H34A 109.5 . . ?
Cl1 C34 H34B 109.5 . . ?
Cl2 C34 Cl1 110.92(12) . . ?
Cl2 C34 H34A 109.5 . . ?
Cl2 C34 H34B 109.5 . . ?
H34A C34 H34B 108.0 . . ?
C19 C20 H20 118.6 . . ?
C21 C20 C19 122.9(2) . . ?
C21 C20 H20 118.6 . . ?
C32 C31 H31 119.8 . . ?
C30 C31 C32 120.5(2) . . ?
C30 C31 H31 119.8 . . ?
N3 B1 C28 109.68(15) . . ?
N5 B1 N3 101.41(15) . . ?
N5 B1 C28 109.43(16) . . ?
N1 B1 N3 106.14(15) . . ?
N1 B1 N5 117.59(15) . . ?
N1 B1 C28 111.84(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
N3 C16 C15 C14 -1.8(3) . . . . ?
N3 C12 C13 C14 3.2(3) . . . . ?
N5 C26 C27 C18 -1.2(2) . . . . ?
N5 C26 C27 C22 178.72(18) . . . . ?
N4 C16 C15 C14 174.53(18) . . . . ?
N1 C1 C2 C3 177.12(19) . . . . ?
N1 C11 C9 C10 4.8(2) . . . . ?
N1 C11 C9 C8 179.4(2) . . . . ?
N2 C11 C9 C10 -169.90(18) . . . . ?
N2 C11 C9 C8 4.7(4) . . . . ?
N2 C12 C13 C14 -176.32(18) . . . . ?
C10 C1 C2 C3 1.2(3) . . . . ?
C10 C5 C4 C3 0.5(3) . . . . ?
C10 C5 C6 C7 -1.7(3) . . . . ?
C10 C9 C8 C7 -0.9(3) . . . . ?
C1 N1 C11 N2 168.46(19) . . . . ?
C1 N1 C11 C9 -6.0(2) . . . . ?
C1 N1 B1 N3 -172.76(17) . . . . ?
C1 N1 B1 N5 74.7(2) . . . . ?
C1 N1 B1 C28 -53.2(2) . . . . ?
C1 C10 C5 C4 0.1(3) . . . . ?
C1 C10 C5 C6 177.97(18) . . . . ?
C1 C10 C9 C11 -1.7(2) . . . . ?
C1 C10 C9 C8 -177.31(19) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C5 C10 C1 N1 -177.87(18) . . . . ?
C5 C10 C1 C2 -0.9(3) . . . . ?
C5 C10 C9 C11 174.29(18) . . . . ?
C5 C10 C9 C8 -1.3(3) . . . . ?
C5 C4 C3 C2 -0.2(3) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C28 C33 C32 C31 -0.2(3) . . . . ?
C28 C29 C30 C31 -1.1(4) . . . . ?
C16 N3 C12 N2 171.46(17) . . . . ?
C16 N3 C12 C13 -8.1(3) . . . . ?
C16 N3 B1 N5 -47.45(19) . . . . ?
C16 N3 B1 N1 -170.83(15) . . . . ?
C16 N3 B1 C28 68.2(2) . . . . ?
C16 N4 C17 N5 -10.2(3) . . . . ?
C16 N4 C17 C18 168.42(18) . . . . ?
C16 C15 C14 C13 -3.0(3) . . . . ?
C11 N1 C1 C10 5.0(2) . . . . ?
C11 N1 C1 C2 -171.3(2) . . . . ?
C11 N1 B1 N3 -6.2(2) . . . . ?
C11 N1 B1 N5 -118.78(19) . . . . ?
C11 N1 B1 C28 113.36(19) . . . . ?
C11 N2 C12 N3 3.3(3) . . . . ?
C11 N2 C12 C13 -177.17(18) . . . . ?
C11 C9 C8 C7 -174.9(2) . . . . ?
C9 C10 C1 N1 -1.9(2) . . . . ?
C9 C10 C1 C2 175.02(18) . . . . ?
C9 C10 C5 C4 -175.29(18) . . . . ?
C9 C10 C5 C6 2.6(3) . . . . ?
C9 C8 C7 C6 1.7(4) . . . . ?
C25 C26 C27 C18 177.18(17) . . . . ?
C25 C26 C27 C22 -2.9(3) . . . . ?
C25 C24 C23 C22 -1.4(3) . . . . ?
C26 N5 C17 N4 175.96(18) . . . . ?
C26 N5 C17 C18 -2.8(2) . . . . ?
C26 N5 B1 N3 -160.62(18) . . . . ?
C26 N5 B1 N1 -45.4(3) . . . . ?
C26 N5 B1 C28 83.6(2) . . . . ?
C26 C25 C24 C23 -0.3(3) . . . . ?
C26 C27 C22 C23 1.1(3) . . . . ?
C26 C27 C22 C21 -178.70(19) . . . . ?
C18 C27 C22 C23 -178.99(19) . . . . ?
C18 C27 C22 C21 1.2(3) . . . . ?
C18 C19 C20 C21 0.9(3) . . . . ?
C17 N5 C26 C25 -175.5(2) . . . . ?
C17 N5 C26 C27 2.5(2) . . . . ?
C17 N5 B1 N3 53.64(19) . . . . ?
C17 N5 B1 N1 168.82(16) . . . . ?
C17 N5 B1 C28 -62.2(2) . . . . ?
C17 N4 C16 N3 18.5(3) . . . . ?
C17 N4 C16 C15 -157.75(18) . . . . ?
C17 C18 C27 C26 -0.5(2) . . . . ?
C17 C18 C27 C22 179.59(19) . . . . ?
C17 C18 C19 C20 179.3(2) . . . . ?
C4 C5 C6 C7 175.8(2) . . . . ?
C27 C18 C17 N5 2.1(2) . . . . ?
C27 C18 C17 N4 -176.71(19) . . . . ?
C27 C18 C19 C20 -0.6(3) . . . . ?
C27 C22 C23 C24 1.0(3) . . . . ?
C27 C22 C21 C20 -0.8(3) . . . . ?
C12 N3 C16 N4 -168.92(17) . . . . ?
C12 N3 C16 C15 7.3(3) . . . . ?
C12 N3 B1 N5 135.59(17) . . . . ?
C12 N3 B1 N1 12.2(2) . . . . ?
C12 N3 B1 C28 -108.77(19) . . . . ?
C12 N2 C11 N1 3.0(3) . . . . ?
C12 N2 C11 C9 176.72(18) . . . . ?
C15 C14 C13 C12 2.3(3) . . . . ?
C24 C25 C26 N5 -179.75(19) . . . . ?
C24 C25 C26 C27 2.4(3) . . . . ?
C22 C21 C20 C19 -0.1(3) . . . . ?
C33 C28 C29 C30 -0.7(3) . . . . ?
C33 C28 B1 N3 43.4(2) . . . . ?
C33 C28 B1 N5 153.85(18) . . . . ?
C33 C28 B1 N1 -74.1(2) . . . . ?
C33 C32 C31 C30 -1.6(3) . . . . ?
C6 C5 C4 C3 -177.1(2) . . . . ?
C29 C28 C33 C32 1.3(3) . . . . ?
C29 C28 B1 N3 -134.16(19) . . . . ?
C29 C28 B1 N5 -23.7(3) . . . . ?
C29 C28 B1 N1 108.4(2) . . . . ?
C29 C30 C31 C32 2.2(4) . . . . ?
C19 C18 C17 N5 -177.8(2) . . . . ?
C19 C18 C17 N4 3.4(4) . . . . ?
C19 C18 C27 C26 179.40(18) . . . . ?
C19 C18 C27 C22 -0.5(3) . . . . ?
C23 C22 C21 C20 179.4(2) . . . . ?
C21 C22 C23 C24 -179.2(2) . . . . ?
B1 N3 C16 N4 14.0(2) . . . . ?
B1 N3 C16 C15 -169.73(17) . . . . ?
B1 N3 C12 N2 -11.7(3) . . . . ?
B1 N3 C12 C13 168.79(17) . . . . ?
B1 N5 C26 C25 37.8(3) . . . . ?
B1 N5 C26 C27 -144.20(19) . . . . ?
B1 N5 C17 N4 -29.9(3) . . . . ?
B1 N5 C17 C18 151.32(16) . . . . ?
B1 N1 C1 C10 172.92(17) . . . . ?
B1 N1 C1 C2 -3.3(3) . . . . ?
B1 N1 C11 N2 -0.6(3) . . . . ?
B1 N1 C11 C9 -175.14(16) . . . . ?
B1 C28 C33 C32 -176.43(19) . . . . ?
B1 C28 C29 C30 177.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.658
_oxdiff_exptl_absorpt_empirical_full_min 0.550
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
