# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

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

data_210922_ysg_hashizume_01_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2215757'
loop_
_audit_author_name
_audit_author_address
'Yusuke Yoshigoe'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-10-27 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-10-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 B N'
_chemical_formula_sum            'C24 H18 B N'
_chemical_formula_weight         331.20
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   11.1612(9)
_cell_length_b                   17.6966(14)
_cell_length_c                   9.0820(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1793.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6418
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5957
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1304 before and 0.0726 after correction.
The Ratio of minimum to maximum transmission is 0.7983.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platelet
_exptl_crystal_F_000             696
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 -1.00 0.0470
0.00 -1.00 1.00 0.2200
-1.00 -1.00 0.00 0.2200
1.00 1.00 0.00 0.0840
1.00 0.00 1.00 0.0870
0.00 -1.00 -1.00 0.0760
0.00 -1.00 0.00 0.1450
0.00 1.00 0.00 0.0290
1.00 -1.00 0.00 0.1440
-1.00 1.00 0.00 0.1230
1.00 -1.00 1.00 0.1230
-1.00 1.00 -1.00 0.1290
1.00 1.00 1.00 0.0690
-1.00 -1.00 -1.00 0.1550
1.00 -1.00 -1.00 0.1270
-1.00 1.00 1.00 0.2090

_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.256
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_av_unetI/netI     0.0928
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20668
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.280
_diffrn_reflns_theta_min         2.157
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.675
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.769
_reflns_number_gt                3501
_reflns_number_total             4877
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.131
_refine_ls_abs_structure_details 
;
 Flack x determined using 1104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(10)
_refine_ls_extinction_coef       0.23(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4877
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0900
_refine_ls_restrained_S_all      1.088
_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)+(0.1129P)²+0.7937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2258
_refine_ls_wR_factor_ref         0.2425
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C20, C19, C21, C3, C14, C18
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C1(H1), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11),
 C12(H12), C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C22 C -0.2925(5) -0.3908(4) -0.2954(6) 0.0662(15) Uani 1 1 d . . . . .
H22 H -0.317716 -0.430091 -0.356009 0.079 Uiso 1 1 calc R U . . .
N2 N -0.4557(3) -0.3081(2) -0.5568(4) 0.0413(8) Uani 1 1 d . . . . .
C24 C -0.5919(4) -0.3495(2) -0.3669(4) 0.0378(9) Uani 1 1 d . . . . .
C23 C -0.7303(4) -0.4191(2) -0.5263(5) 0.0414(10) Uani 1 1 d . . . . .
H23 H -0.751494 -0.436701 -0.619233 0.050 Uiso 1 1 calc R U . . .
C1 C -0.1552(5) -0.3389(5) -0.1204(6) 0.078(2) Uani 1 1 d . . . . .
H1 H -0.086855 -0.343150 -0.062432 0.094 Uiso 1 1 calc R U . . .
C2 C -0.1890(5) -0.4014(4) -0.2064(8) 0.0797(19) Uani 1 1 d . . . . .
C3 C -0.3558(4) -0.3252(3) -0.2947(5) 0.0542(12) Uani 1 1 d . . . . .
C4 C -0.5413(4) -0.3531(2) -0.6188(4) 0.0371(8) Uani 1 1 d . . . . .
C5 C -0.5357(4) -0.3695(2) -0.7689(5) 0.0462(10) Uani 1 1 d . . . . .
H5 H -0.594030 -0.399730 -0.812333 0.055 Uiso 1 1 calc R U . . .
C6 C -0.4437(5) -0.3407(3) -0.8524(5) 0.0528(12) Uani 1 1 d . . . . .
H6 H -0.438833 -0.351759 -0.952366 0.063 Uiso 1 1 calc R U . . .
C7 C -0.1230(7) -0.4716(5) -0.2116(10) 0.104(3) Uani 1 1 d . . . . .
H7A H -0.080151 -0.478337 -0.120885 0.156 Uiso 1 1 calc R U . . .
H7B H -0.067159 -0.470159 -0.292018 0.156 Uiso 1 1 calc R U . . .
H7C H -0.177686 -0.512801 -0.225376 0.156 Uiso 1 1 calc R U . . .
C8 C -0.3658(4) -0.2795(3) -0.6405(5) 0.0478(10) Uani 1 1 d . . . . .
H8 H -0.308509 -0.248633 -0.596682 0.057 Uiso 1 1 calc R U . . .
C9 C -0.3576(5) -0.2947(3) -0.7863(5) 0.0550(12) Uani 1 1 d . . . . .
H9 H -0.295092 -0.274727 -0.841818 0.066 Uiso 1 1 calc R U . . .
C10 C -0.6265(4) -0.3763(2) -0.5064(4) 0.0360(8) Uani 1 1 d . . . . .
C11 C -0.6635(4) -0.3677(2) -0.2479(5) 0.0438(10) Uani 1 1 d . . . . .
H11 H -0.642150 -0.351407 -0.154136 0.053 Uiso 1 1 calc R U . . .
C12 C -0.7674(4) -0.4102(2) -0.2670(5) 0.0446(10) Uani 1 1 d . . . . .
H12 H -0.814653 -0.422023 -0.185930 0.054 Uiso 1 1 calc R U . . .
C13 C -0.8009(4) -0.4349(2) -0.4052(5) 0.0440(10) Uani 1 1 d . . . . .
H13 H -0.871310 -0.462392 -0.416798 0.053 Uiso 1 1 calc R U . . .
C14 C -0.4816(5) -0.2103(3) -0.3298(5) 0.0578(13) Uani 1 1 d . . . . .
C15 C -0.5564(5) -0.1520(3) -0.3708(7) 0.0644(15) Uani 1 1 d . . . . .
H15 H -0.614296 -0.159873 -0.442798 0.077 Uiso 1 1 calc R U . . .
C16 C -0.5453(6) -0.0803(3) -0.3038(8) 0.0766(19) Uani 1 1 d . . . . .
H16 H -0.594835 -0.040797 -0.333306 0.092 Uiso 1 1 calc R U . . .
C17 C -0.4618(6) -0.0686(4) -0.1953(8) 0.0746(19) Uani 1 1 d . . . . .
H17 H -0.456452 -0.021693 -0.149803 0.090 Uiso 1 1 calc R U . . .
C18 C -0.3858(5) -0.1262(4) -0.1533(6) 0.0674(17) Uani 1 1 d . . . . .
H18 H -0.329684 -0.117914 -0.079282 0.081 Uiso 1 1 calc R U . . .
C19 C -0.3928(5) -0.1976(3) -0.2223(5) 0.0611(12) Uani 1 1 d . . . . .
C20 C -0.3175(5) -0.2632(4) -0.2034(5) 0.0611(12) Uani 1 1 d . . . . .
C21 C -0.2168(6) -0.2726(5) -0.1169(6) 0.0725(17) Uani 1 1 d . . . . .
H21 H -0.191005 -0.233465 -0.056249 0.087 Uiso 1 1 calc R U . . .
B1 B -0.4737(5) -0.2988(3) -0.3829(5) 0.0466(11) 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
C22 H22 0.9300 . ?
C22 C2 1.422(8) . ?
C22 C3 1.359(8) . ?
N2 C4 1.365(5) . ?
N2 C8 1.357(6) . ?
N2 B1 1.600(6) . ?
C24 C10 1.407(5) . ?
C24 C11 1.383(6) . ?
C24 B1 1.603(6) . ?
C23 H23 0.9300 . ?
C23 C10 1.396(6) . ?
C23 C13 1.381(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.405(10) . ?
C1 C21 1.361(11) . ?
C2 C7 1.445(11) . ?
C3 C20 1.441(7) . ?
C3 B1 1.610(7) . ?
C4 C5 1.395(6) . ?
C4 C10 1.455(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(7) . ?
C6 H6 0.9300 . ?
C6 C9 1.395(7) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9300 . ?
C8 C9 1.355(7) . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.393(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(8) . ?
C14 C19 1.409(7) . ?
C14 B1 1.641(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.413(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(10) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(10) . ?
C18 H18 0.9300 . ?
C18 C19 1.413(8) . ?
C19 C20 1.443(9) . ?
C20 C21 1.381(8) . ?
C21 H21 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
C2 C22 H22 118.9 . . ?
C3 C22 H22 118.9 . . ?
C3 C22 C2 122.1(6) . . ?
C4 N2 B1 112.3(3) . . ?
C8 N2 C4 120.3(4) . . ?
C8 N2 B1 127.3(4) . . ?
C10 C24 B1 109.5(4) . . ?
C11 C24 C10 117.8(4) . . ?
C11 C24 B1 132.6(4) . . ?
C10 C23 H23 120.7 . . ?
C13 C23 H23 120.7 . . ?
C13 C23 C10 118.7(4) . . ?
C2 C1 H1 118.1 . . ?
C21 C1 H1 118.1 . . ?
C21 C1 C2 123.8(6) . . ?
C22 C2 C7 120.6(7) . . ?
C1 C2 C22 115.5(6) . . ?
C1 C2 C7 123.9(7) . . ?
C22 C3 C20 120.0(5) . . ?
C22 C3 B1 132.1(5) . . ?
C20 C3 B1 107.9(5) . . ?
N2 C4 C5 119.6(4) . . ?
N2 C4 C10 109.4(3) . . ?
C5 C4 C10 131.0(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.7(4) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C9 119.6(4) . . ?
C9 C6 H6 120.2 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8 119.2 . . ?
C9 C8 N2 121.6(4) . . ?
C9 C8 H8 119.2 . . ?
C6 C9 H9 120.3 . . ?
C8 C9 C6 119.3(5) . . ?
C8 C9 H9 120.3 . . ?
C24 C10 C4 110.9(3) . . ?
C23 C10 C24 121.8(4) . . ?
C23 C10 C4 127.2(4) . . ?
C24 C11 H11 119.7 . . ?
C24 C11 C12 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.7 . . ?
C23 C13 C12 120.3(4) . . ?
C23 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C19 119.6(5) . . ?
C15 C14 B1 131.9(5) . . ?
C19 C14 B1 108.6(5) . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.2(6) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.2(7) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(5) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(6) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 119.3(6) . . ?
C14 C19 C20 111.3(5) . . ?
C18 C19 C20 129.4(5) . . ?
C3 C20 C19 111.8(5) . . ?
C21 C20 C3 118.5(6) . . ?
C21 C20 C19 129.7(5) . . ?
C1 C21 C20 120.1(6) . . ?
C1 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
N2 B1 C24 97.7(3) . . ?
N2 B1 C3 111.0(4) . . ?
N2 B1 C14 113.3(4) . . ?
C24 B1 C3 117.7(4) . . ?
C24 B1 C14 117.6(4) . . ?
C3 B1 C14 100.1(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
C22 C3 C20 C19 177.5(4) . . . . ?
C22 C3 C20 C21 -0.7(7) . . . . ?
C22 C3 B1 N2 -54.8(7) . . . . ?
C22 C3 B1 C24 56.6(7) . . . . ?
C22 C3 B1 C14 -174.7(5) . . . . ?
N2 C4 C5 C6 0.6(6) . . . . ?
N2 C4 C10 C24 -3.5(5) . . . . ?
N2 C4 C10 C23 176.4(4) . . . . ?
N2 C8 C9 C6 0.3(8) . . . . ?
C24 C11 C12 C13 0.0(6) . . . . ?
C2 C22 C3 C20 1.0(8) . . . . ?
C2 C22 C3 B1 179.8(5) . . . . ?
C2 C1 C21 C20 -1.3(9) . . . . ?
C3 C22 C2 C1 -1.3(8) . . . . ?
C3 C22 C2 C7 -179.2(6) . . . . ?
C3 C20 C21 C1 0.8(7) . . . . ?
C4 N2 C8 C9 -0.4(7) . . . . ?
C4 N2 B1 C24 -0.6(5) . . . . ?
C4 N2 B1 C3 123.0(4) . . . . ?
C4 N2 B1 C14 -125.2(4) . . . . ?
C4 C5 C6 C9 -0.7(7) . . . . ?
C5 C4 C10 C24 176.4(4) . . . . ?
C5 C4 C10 C23 -3.7(7) . . . . ?
C5 C6 C9 C8 0.3(8) . . . . ?
C8 N2 C4 C5 0.0(6) . . . . ?
C8 N2 C4 C10 179.9(4) . . . . ?
C8 N2 B1 C24 -177.9(4) . . . . ?
C8 N2 B1 C3 -54.2(6) . . . . ?
C8 N2 B1 C14 57.5(6) . . . . ?
C10 C24 C11 C12 -1.0(6) . . . . ?
C10 C24 B1 N2 -1.4(5) . . . . ?
C10 C24 B1 C3 -120.2(4) . . . . ?
C10 C24 B1 C14 120.0(4) . . . . ?
C10 C23 C13 C12 -1.5(6) . . . . ?
C10 C4 C5 C6 -179.3(4) . . . . ?
C11 C24 C10 C23 0.8(6) . . . . ?
C11 C24 C10 C4 -179.3(4) . . . . ?
C11 C24 B1 N2 -178.7(4) . . . . ?
C11 C24 B1 C3 62.6(7) . . . . ?
C11 C24 B1 C14 -57.3(7) . . . . ?
C11 C12 C13 C23 1.3(7) . . . . ?
C13 C23 C10 C24 0.4(6) . . . . ?
C13 C23 C10 C4 -179.4(4) . . . . ?
C14 C15 C16 C17 -1.4(8) . . . . ?
C14 C19 C20 C3 -2.4(5) . . . . ?
C14 C19 C20 C21 175.5(5) . . . . ?
C15 C14 C19 C18 3.0(6) . . . . ?
C15 C14 C19 C20 -175.2(4) . . . . ?
C15 C14 B1 N2 56.5(7) . . . . ?
C15 C14 B1 C24 -56.5(7) . . . . ?
C15 C14 B1 C3 174.8(5) . . . . ?
C15 C16 C17 C18 1.7(8) . . . . ?
C16 C17 C18 C19 0.3(8) . . . . ?
C17 C18 C19 C14 -2.7(7) . . . . ?
C17 C18 C19 C20 175.1(5) . . . . ?
C18 C19 C20 C3 179.7(4) . . . . ?
C18 C19 C20 C21 -2.4(8) . . . . ?
C19 C14 C15 C16 -1.0(7) . . . . ?
C19 C14 B1 N2 -124.0(4) . . . . ?
C19 C14 B1 C24 123.1(4) . . . . ?
C19 C14 B1 C3 -5.7(4) . . . . ?
C19 C20 C21 C1 -177.0(5) . . . . ?
C20 C3 B1 N2 124.2(4) . . . . ?
C20 C3 B1 C24 -124.4(4) . . . . ?
C20 C3 B1 C14 4.3(4) . . . . ?
C21 C1 C2 C22 1.5(9) . . . . ?
C21 C1 C2 C7 179.2(6) . . . . ?
B1 N2 C4 C5 -177.5(4) . . . . ?
B1 N2 C4 C10 2.4(5) . . . . ?
B1 N2 C8 C9 176.6(5) . . . . ?
B1 C24 C10 C23 -176.9(4) . . . . ?
B1 C24 C10 C4 3.0(5) . . . . ?
B1 C24 C11 C12 176.0(4) . . . . ?
B1 C3 C20 C19 -1.6(5) . . . . ?
B1 C3 C20 C21 -179.8(4) . . . . ?
B1 C14 C15 C16 178.5(5) . . . . ?
B1 C14 C19 C18 -176.6(4) . . . . ?
B1 C14 C19 C20 5.2(5) . . . . ?

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

data_220226_ysg_hashizume_01_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2203027'
loop_
_audit_author_name
_audit_author_address
'Yusuke Yoshigoe'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-08-23 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-02-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 B N'
_chemical_formula_sum            'C24 H18 B N'
_chemical_formula_weight         331.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.2016(13)
_cell_length_b                   9.8758(12)
_cell_length_c                   14.9890(18)
_cell_angle_alpha                90
_cell_angle_beta                 103.647(4)
_cell_angle_gamma                90
_cell_volume                     1755.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5431
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      29.265
_cell_measurement_theta_min      2.491
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.999
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0817 before and 0.0578 after correction.
The Ratio of minimum to maximum transmission is 0.8941.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_preparation       diffusion
_exptl_crystal_recrystallization_method diffusion
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20780
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.947
_diffrn_reflns_theta_min         2.492
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_special_details          none
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3258
_reflns_number_total             4663
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       0.067(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4663
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.080
_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)+(0.0808P)²+0.2451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1586
_refine_special_details          none
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17),
 C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
C1 C 0.06700(15) 0.83856(18) 0.80397(13) 0.0471(4) Uani 1 1 d . . . . .
H1A H 0.055088 0.805581 0.861184 0.071 Uiso 1 1 calc R U . . .
H1B H -0.003046 0.871072 0.766580 0.071 Uiso 1 1 calc R U . . .
H1C H 0.120881 0.911098 0.815539 0.071 Uiso 1 1 calc R U . . .
C2 C 0.11104(13) 0.72556(15) 0.75472(11) 0.0333(3) Uani 1 1 d . . . . .
C3 C 0.21203(12) 0.66078(14) 0.79572(10) 0.0303(3) Uani 1 1 d . . . . .
H3 H 0.250970 0.685915 0.854453 0.036 Uiso 1 1 calc R U . . .
C4 C 0.25490(11) 0.55922(14) 0.74969(9) 0.0273(3) Uani 1 1 d . . . . .
C5 C 0.19763(12) 0.51617(15) 0.66143(10) 0.0299(3) Uani 1 1 d . . . . .
B1 B 0.26828(15) 0.39669(17) 0.62720(11) 0.0315(4) Uani 1 1 d . . . . .
C7 C 0.21468(12) 0.25070(15) 0.59588(10) 0.0298(3) Uani 1 1 d . . . . .
C8 C 0.23056(12) 0.21752(15) 0.50865(10) 0.0300(3) Uani 1 1 d . . . . .
C9 C 0.19814(12) 0.09288(15) 0.46650(11) 0.0347(4) Uani 1 1 d . . . . .
H9 H 0.208983 0.074146 0.408387 0.042 Uiso 1 1 calc R U . . .
C10 C 0.14981(13) -0.00154(16) 0.51288(12) 0.0390(4) Uani 1 1 d . . . . .
H10 H 0.128065 -0.085358 0.486266 0.047 Uiso 1 1 calc R U . . .
C11 C 0.36274(12) 0.48548(14) 0.78056(10) 0.0284(3) Uani 1 1 d . . . . .
C12 C 0.44439(12) 0.49985(15) 0.86188(10) 0.0322(3) Uani 1 1 d . . . . .
H12 H 0.433475 0.560332 0.906554 0.039 Uiso 1 1 calc R U . . .
C13 C 0.54310(13) 0.42289(16) 0.87626(11) 0.0367(4) Uani 1 1 d . . . . .
H13 H 0.598960 0.433881 0.929931 0.044 Uiso 1 1 calc R U . . .
C14 C 0.55788(13) 0.33036(16) 0.81078(11) 0.0368(4) Uani 1 1 d . . . . .
H14 H 0.623975 0.279878 0.820300 0.044 Uiso 1 1 calc R U . . .
C15 C 0.47441(13) 0.31269(16) 0.73098(11) 0.0349(4) Uani 1 1 d . . . . .
H15 H 0.483608 0.247197 0.688767 0.042 Uiso 1 1 calc R U . . .
C16 C 0.37719(12) 0.39141(14) 0.71313(10) 0.0291(3) Uani 1 1 d . . . . .
C17 C 0.09768(13) 0.58199(16) 0.62134(11) 0.0358(4) Uani 1 1 d . . . . .
H17 H 0.058323 0.556808 0.562739 0.043 Uiso 1 1 calc R U . . .
C18 C 0.05505(13) 0.68486(16) 0.66688(12) 0.0380(4) Uani 1 1 d . . . . .
H18 H -0.012076 0.727187 0.638100 0.046 Uiso 1 1 calc R U . . .
C19 C 0.16514(13) 0.15288(16) 0.64061(11) 0.0369(4) Uani 1 1 d . . . . .
H19 H 0.153200 0.171193 0.698440 0.044 Uiso 1 1 calc R U . . .
C20 C 0.13339(14) 0.02828(17) 0.59971(12) 0.0417(4) Uani 1 1 d . . . . .
H20 H 0.100754 -0.036114 0.630631 0.050 Uiso 1 1 calc R U . . .
C21 C 0.28416(12) 0.32916(14) 0.47164(10) 0.0295(3) Uani 1 1 d . . . . .
C22 C 0.31497(13) 0.34006(16) 0.38824(10) 0.0330(3) Uani 1 1 d . . . . .
H22 H 0.303366 0.268135 0.347028 0.040 Uiso 1 1 calc R U . . .
C23 C 0.36279(13) 0.45852(16) 0.36756(10) 0.0366(4) Uani 1 1 d . . . . .
H23 H 0.383127 0.467646 0.311841 0.044 Uiso 1 1 calc R U . . .
C24 C 0.38058(14) 0.56450(16) 0.43023(11) 0.0364(4) Uani 1 1 d . . . . .
H24 H 0.412204 0.645310 0.416592 0.044 Uiso 1 1 calc R U . . .
C25 C 0.35101(13) 0.54883(16) 0.51259(11) 0.0348(4) Uani 1 1 d . . . . .
H25 H 0.363745 0.619271 0.554965 0.042 Uiso 1 1 calc R U . . .
N1 N 0.30394(11) 0.43322(12) 0.53287(8) 0.0310(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.505(2) . ?
C2 C3 1.396(2) . ?
C2 C18 1.392(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.3878(19) . ?
C4 C5 1.4081(19) . ?
C4 C11 1.4793(19) . ?
C5 B1 1.615(2) . ?
C5 C17 1.387(2) . ?
B1 C7 1.607(2) . ?
B1 C16 1.619(2) . ?
B1 N1 1.615(2) . ?
C7 C8 1.405(2) . ?
C7 C19 1.393(2) . ?
C8 C9 1.397(2) . ?
C8 C21 1.457(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(2) . ?
C10 H10 0.9300 . ?
C10 C20 1.394(2) . ?
C11 C12 1.388(2) . ?
C11 C16 1.414(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.397(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.389(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.392(2) . ?
C21 N1 1.3608(18) . ?
C22 H22 0.9300 . ?
C22 C23 1.375(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.389(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.374(2) . ?
C25 H25 0.9300 . ?
C25 N1 1.3447(19) . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.27(15) . . ?
C18 C2 C1 121.71(15) . . ?
C18 C2 C3 118.00(14) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.63(14) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 121.57(13) . . ?
C3 C4 C11 127.73(13) . . ?
C5 C4 C11 110.66(12) . . ?
C4 C5 B1 109.59(13) . . ?
C17 C5 C4 117.14(14) . . ?
C17 C5 B1 133.26(14) . . ?
C5 B1 C16 99.80(12) . . ?
C5 B1 N1 112.90(12) . . ?
C7 B1 C5 122.51(13) . . ?
C7 B1 C16 113.88(12) . . ?
C7 B1 N1 96.88(11) . . ?
N1 B1 C16 111.33(12) . . ?
C8 C7 B1 110.19(12) . . ?
C19 C7 B1 132.43(13) . . ?
C19 C7 C8 117.20(13) . . ?
C7 C8 C21 110.53(13) . . ?
C9 C8 C7 122.66(14) . . ?
C9 C8 C21 126.81(14) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.54(15) . . ?
C10 C9 H9 120.7 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C20 120.10(15) . . ?
C20 C10 H10 119.9 . . ?
C12 C11 C4 128.73(13) . . ?
C12 C11 C16 120.68(13) . . ?
C16 C11 C4 110.58(13) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.60(14) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.12(15) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.18(14) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.01(14) . . ?
C16 C15 H15 119.5 . . ?
C11 C16 B1 109.28(12) . . ?
C15 C16 B1 132.38(13) . . ?
C15 C16 C11 118.32(14) . . ?
C5 C17 H17 119.3 . . ?
C5 C17 C18 121.45(15) . . ?
C18 C17 H17 119.3 . . ?
C2 C18 H18 119.4 . . ?
C17 C18 C2 121.20(14) . . ?
C17 C18 H18 119.4 . . ?
C7 C19 H19 119.7 . . ?
C20 C19 C7 120.65(15) . . ?
C20 C19 H19 119.7 . . ?
C10 C20 H20 119.6 . . ?
C19 C20 C10 120.85(15) . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C8 129.88(14) . . ?
N1 C21 C8 109.81(12) . . ?
N1 C21 C22 120.31(13) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 C21 119.16(14) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.71(14) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.38(15) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.5 . . ?
N1 C25 C24 121.02(15) . . ?
N1 C25 H25 119.5 . . ?
C21 N1 B1 112.34(12) . . ?
C25 N1 B1 127.24(12) . . ?
C25 N1 C21 120.40(13) . . ?

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
C1 C2 C3 C4 -178.10(13) . . . . ?
C1 C2 C18 C17 178.77(14) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C2 C3 C4 C11 176.53(13) . . . . ?
C3 C2 C18 C17 0.5(2) . . . . ?
C3 C4 C5 B1 -179.54(12) . . . . ?
C3 C4 C5 C17 1.6(2) . . . . ?
C3 C4 C11 C12 0.6(2) . . . . ?
C3 C4 C11 C16 -178.68(13) . . . . ?
C4 C5 B1 C7 123.87(15) . . . . ?
C4 C5 B1 C16 -2.81(14) . . . . ?
C4 C5 B1 N1 -121.08(14) . . . . ?
C4 C5 C17 C18 -0.9(2) . . . . ?
C4 C11 C12 C13 -177.62(13) . . . . ?
C4 C11 C16 B1 -1.24(16) . . . . ?
C4 C11 C16 C15 -179.84(12) . . . . ?
C5 C4 C11 C12 178.56(14) . . . . ?
C5 C4 C11 C16 -0.70(16) . . . . ?
C5 B1 C7 C8 127.50(15) . . . . ?
C5 B1 C7 C19 -57.6(2) . . . . ?
C5 B1 C16 C11 2.38(14) . . . . ?
C5 B1 C16 C15 -179.28(15) . . . . ?
C5 B1 N1 C21 -134.31(13) . . . . ?
C5 B1 N1 C25 47.5(2) . . . . ?
C5 C17 C18 C2 -0.2(2) . . . . ?
B1 C5 C17 C18 -179.43(15) . . . . ?
B1 C7 C8 C9 176.25(14) . . . . ?
B1 C7 C8 C21 -3.56(17) . . . . ?
B1 C7 C19 C20 -174.58(16) . . . . ?
C7 B1 C16 C11 -129.92(13) . . . . ?
C7 B1 C16 C15 48.4(2) . . . . ?
C7 B1 N1 C21 -4.61(15) . . . . ?
C7 B1 N1 C25 177.18(14) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
C7 C8 C21 C22 -179.86(15) . . . . ?
C7 C8 C21 N1 0.37(17) . . . . ?
C7 C19 C20 C10 -0.3(2) . . . . ?
C8 C7 C19 C20 0.1(2) . . . . ?
C8 C9 C10 C20 0.4(2) . . . . ?
C8 C21 C22 C23 178.51(15) . . . . ?
C8 C21 N1 B1 3.01(17) . . . . ?
C8 C21 N1 C25 -178.64(13) . . . . ?
C9 C8 C21 C22 0.3(3) . . . . ?
C9 C8 C21 N1 -179.44(14) . . . . ?
C9 C10 C20 C19 0.1(2) . . . . ?
C11 C4 C5 B1 2.33(16) . . . . ?
C11 C4 C5 C17 -176.56(12) . . . . ?
C11 C12 C13 C14 -1.7(2) . . . . ?
C12 C11 C16 B1 179.43(12) . . . . ?
C12 C11 C16 C15 0.8(2) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 C16 3.1(2) . . . . ?
C14 C15 C16 B1 178.63(15) . . . . ?
C14 C15 C16 C11 -3.2(2) . . . . ?
C16 B1 C7 C8 -112.30(14) . . . . ?
C16 B1 C7 C19 62.6(2) . . . . ?
C16 B1 N1 C21 114.38(14) . . . . ?
C16 B1 N1 C25 -63.83(19) . . . . ?
C16 C11 C12 C13 1.6(2) . . . . ?
C17 C5 B1 C7 -57.5(2) . . . . ?
C17 C5 B1 C16 175.84(16) . . . . ?
C17 C5 B1 N1 57.6(2) . . . . ?
C18 C2 C3 C4 0.2(2) . . . . ?
C19 C7 C8 C9 0.5(2) . . . . ?
C19 C7 C8 C21 -179.35(13) . . . . ?
C21 C8 C9 C10 179.07(14) . . . . ?
C21 C22 C23 C24 0.6(2) . . . . ?
C22 C21 N1 B1 -176.79(13) . . . . ?
C22 C21 N1 C25 1.6(2) . . . . ?
C22 C23 C24 C25 0.6(2) . . . . ?
C23 C24 C25 N1 -0.8(2) . . . . ?
C24 C25 N1 B1 177.80(14) . . . . ?
C24 C25 N1 C21 -0.3(2) . . . . ?
N1 B1 C7 C8 4.70(15) . . . . ?
N1 B1 C7 C19 179.61(15) . . . . ?
N1 B1 C16 C11 121.82(13) . . . . ?
N1 B1 C16 C15 -59.8(2) . . . . ?
N1 C21 C22 C23 -1.7(2) . . . . ?

_olex2_exptl_crystal_mounting_method cryoroop
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_220228_ysg_hashizume_02_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2203029'
loop_
_audit_author_name
_audit_author_address
'Yusuke Yoshigoe'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-08-23 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-02-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H15 B F3 N'
_chemical_formula_sum            'C24 H15 B F3 N'
_chemical_formula_weight         385.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.3393(5)
_cell_length_b                   9.3980(3)
_cell_length_c                   15.5279(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.4660(10)
_cell_angle_gamma                90
_cell_volume                     1823.75(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7675
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      29.858
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.998
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1263 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.9371.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_preparation       diffusion
_exptl_crystal_recrystallization_method diffusion
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.125
_diffrn_reflns_theta_min         2.580
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_special_details          none
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3967
_reflns_number_total             4967
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.026(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4967
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0742
_refine_ls_restrained_S_all      1.222
_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)+(0.0390P)²+2.3792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.1756
_refine_special_details          none
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F3-F1 \\sim F3-F2 \\sim F1-F2 \\sim F1A-F2A \\sim F1A-F3A \\sim F2A-F3A
 with sigma of 0.04
 C27-F3 \\sim C27-C2 \\sim C27-F1 \\sim C27-F2 \\sim C27-F1A \\sim C27-F2A
\\sim C27-F3A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C27, F2, F3, F1, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C27, F1A, F2A, F3A, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C6, C7, C13
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F3)=Sof(F1)=Sof(F2)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26)
;
_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
N1 N 0.18590(17) 0.5502(2) 0.47879(14) 0.0316(5) Uani 1 1 d . . . . .
F3 F 0.4020(14) 0.168(2) 0.1446(6) 0.079(4) Uani 0.56(3) 1 d D . P A 1
C2 C 0.3926(2) 0.2811(2) 0.27906(17) 0.0288(5) Uani 1 1 d D . . . .
C3 C 0.29326(19) 0.3378(2) 0.22847(15) 0.0268(5) Uani 1 1 d . . . . .
H3 H 0.260196 0.314201 0.166825 0.032 Uiso 1 1 calc R U . . .
C4 C 0.24377(18) 0.4305(2) 0.27116(15) 0.0238(4) Uani 1 1 d . . . . .
C5 C 0.29295(18) 0.4682(2) 0.36434(15) 0.0249(5) Uani 1 1 d . . . . .
C6 C 0.27198(18) 0.7374(2) 0.42554(15) 0.0252(5) Uani 1 1 d . . . . .
C7 C 0.3208(2) 0.8336(3) 0.38564(19) 0.0437(7) Uani 1 1 d . . . . .
H7 H 0.330453 0.809927 0.330922 0.052 Uiso 1 1 calc R U . . .
C8 C 0.3553(3) 0.9639(4) 0.4254(2) 0.0515(8) Uani 1 1 d . . . . .
H8 H 0.388163 1.027064 0.397509 0.062 Uiso 1 1 calc R U . . .
C9 C 0.3415(2) 1.0016(3) 0.5067(2) 0.0453(7) Uani 1 1 d . . . . .
H9 H 0.364578 1.090116 0.532812 0.054 Uiso 1 1 calc R U . . .
C10 C 0.1340(2) 0.5371(3) 0.6369(2) 0.0409(6) Uani 1 1 d . . . . .
H10 H 0.115993 0.531701 0.689520 0.049 Uiso 1 1 calc R U . . .
C11 C 0.1816(2) 0.6582(3) 0.61895(16) 0.0314(5) Uani 1 1 d . . . . .
H11 H 0.196014 0.735398 0.658884 0.038 Uiso 1 1 calc R U . . .
C12 C 0.20783(18) 0.6622(2) 0.53965(15) 0.0246(5) Uani 1 1 d . . . . .
C13 C 0.25937(18) 0.7770(2) 0.50754(15) 0.0252(5) Uani 1 1 d . . . . .
C14 C 0.11980(19) 0.5925(2) 0.29549(15) 0.0265(5) Uani 1 1 d . . . . .
C15 C 0.13900(18) 0.5022(2) 0.23047(15) 0.0241(4) Uani 1 1 d . . . . .
C16 C 0.0639(2) 0.4873(2) 0.14214(15) 0.0287(5) Uani 1 1 d . . . . .
H16 H 0.078082 0.428901 0.099395 0.034 Uiso 1 1 calc R U . . .
C17 C -0.0323(2) 0.5607(3) 0.11876(17) 0.0334(5) Uani 1 1 d . . . . .
H17 H -0.083863 0.548856 0.060681 0.040 Uiso 1 1 calc R U . . .
C18 C -0.0521(2) 0.6516(3) 0.18138(17) 0.0345(6) Uani 1 1 d . . . . .
H18 H -0.116502 0.700903 0.165250 0.041 Uiso 1 1 calc R U . . .
C19 C 0.0250(2) 0.6688(3) 0.26860(17) 0.0319(5) Uani 1 1 d . . . . .
H19 H 0.012522 0.732685 0.309481 0.038 Uiso 1 1 calc R U . . .
C20 C 0.39058(19) 0.4056(3) 0.41426(16) 0.0295(5) Uani 1 1 d . . . . .
H20 H 0.422567 0.425463 0.476592 0.035 Uiso 1 1 calc R U . . .
C21 C 0.4410(2) 0.3135(3) 0.37186(17) 0.0313(5) Uani 1 1 d . . . . .
H21 H 0.506947 0.273712 0.405569 0.038 Uiso 1 1 calc R U . . .
F1 F 0.4545(8) 0.0518(7) 0.2691(7) 0.052(2) Uani 0.56(3) 1 d D . P A 1
F2 F 0.5477(7) 0.2218(13) 0.2501(10) 0.062(2) Uani 0.56(3) 1 d D . P A 1
C24 C 0.1391(2) 0.4316(3) 0.4984(2) 0.0406(6) Uani 1 1 d . . . . .
H24 H 0.124697 0.354485 0.458417 0.049 Uiso 1 1 calc R U . . .
C25 C 0.1130(2) 0.4241(3) 0.5765(2) 0.0469(7) Uani 1 1 d . . . . .
H25 H 0.080959 0.342319 0.588611 0.056 Uiso 1 1 calc R U . . .
C26 C 0.2938(2) 0.9085(3) 0.54889(18) 0.0331(5) Uani 1 1 d . . . . .
H26 H 0.284797 0.932708 0.603782 0.040 Uiso 1 1 calc R U . . .
C27 C 0.4471(2) 0.1834(3) 0.23422(18) 0.0386(6) Uani 1 1 d D . . . .
B2 B 0.2195(2) 0.5851(3) 0.39152(18) 0.0301(6) Uani 1 1 d . . . . .
F1A F 0.5528(7) 0.200(2) 0.2627(10) 0.061(3) Uani 0.44(3) 1 d D . P A 2
F2A F 0.4128(16) 0.204(3) 0.1435(6) 0.070(4) Uani 0.44(3) 1 d D . P A 2
F3A F 0.429(2) 0.0464(11) 0.241(2) 0.100(5) Uani 0.44(3) 1 d D . P A 2


_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
N1 C12 1.376(3) . ?
N1 C24 1.363(3) . ?
N1 B2 1.603(3) . ?
F3 C27 1.317(9) . ?
C2 C3 1.388(3) . ?
C2 C21 1.391(3) . ?
C2 C27 1.487(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(3) . ?
C4 C5 1.409(3) . ?
C4 C15 1.479(3) . ?
C5 C20 1.392(3) . ?
C5 B2 1.623(3) . ?
C6 C7 1.381(4) . ?
C6 C13 1.392(3) . ?
C6 B2 1.600(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(5) . ?
C9 H9 0.9300 . ?
C9 C26 1.375(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(4) . ?
C10 C25 1.380(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(3) . ?
C12 C13 1.457(3) . ?
C13 C26 1.395(3) . ?
C14 C15 1.409(3) . ?
C14 C19 1.385(3) . ?
C14 B2 1.616(4) . ?
C15 C16 1.394(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.394(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.395(3) . ?
C21 H21 0.9300 . ?
F1 C27 1.340(6) . ?
F2 C27 1.327(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.375(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 F1A 1.331(9) . ?
C27 F2A 1.334(9) . ?
C27 F3A 1.320(10) . ?

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
C12 N1 B2 111.64(19) . . ?
C24 N1 C12 118.4(2) . . ?
C24 N1 B2 129.9(2) . . ?
C3 C2 C21 120.5(2) . . ?
C3 C2 C27 119.9(2) . . ?
C21 C2 C27 119.6(2) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 C15 128.0(2) . . ?
C5 C4 C15 110.82(19) . . ?
C4 C5 B2 109.3(2) . . ?
C20 C5 C4 118.4(2) . . ?
C20 C5 B2 132.3(2) . . ?
C7 C6 C13 117.5(2) . . ?
C7 C6 B2 131.1(2) . . ?
C13 C6 B2 111.3(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.9 . . ?
C26 C9 C8 120.2(3) . . ?
C26 C9 H9 119.9 . . ?
C11 C10 H10 120.1 . . ?
C11 C10 C25 119.8(2) . . ?
C25 C10 H10 120.1 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.5(2) . . ?
C12 C11 H11 120.7 . . ?
N1 C12 C11 121.8(2) . . ?
N1 C12 C13 110.11(19) . . ?
C11 C12 C13 128.1(2) . . ?
C6 C13 C12 109.7(2) . . ?
C6 C13 C26 122.2(2) . . ?
C26 C13 C12 128.1(2) . . ?
C15 C14 B2 109.8(2) . . ?
C19 C14 C15 118.1(2) . . ?
C19 C14 B2 132.1(2) . . ?
C14 C15 C4 110.45(19) . . ?
C16 C15 C4 128.4(2) . . ?
C16 C15 C14 121.2(2) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.2(2) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.7(2) . . ?
C19 C18 H18 120.1 . . ?
C14 C19 C18 121.2(2) . . ?
C14 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C5 C20 H20 119.6 . . ?
C5 C20 C21 120.7(2) . . ?
C21 C20 H20 119.6 . . ?
C2 C21 C20 119.9(2) . . ?
C2 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
N1 C24 H24 119.5 . . ?
N1 C24 C25 121.1(2) . . ?
C25 C24 H24 119.5 . . ?
C10 C25 H25 119.8 . . ?
C24 C25 C10 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C9 C26 C13 118.5(2) . . ?
C9 C26 H26 120.8 . . ?
C13 C26 H26 120.8 . . ?
F3 C27 C2 116.4(8) . . ?
F3 C27 F1 105.6(8) . . ?
F3 C27 F2 106.5(9) . . ?
F1 C27 C2 111.1(5) . . ?
F2 C27 C2 111.9(6) . . ?
F2 C27 F1 104.4(6) . . ?
F1A C27 C2 114.0(8) . . ?
F1A C27 F2A 105.4(10) . . ?
F2A C27 C2 111.1(8) . . ?
F3A C27 C2 115.5(7) . . ?
F3A C27 F1A 106.7(10) . . ?
F3A C27 F2A 103.1(11) . . ?
N1 B2 C5 117.0(2) . . ?
N1 B2 C14 113.9(2) . . ?
C6 B2 N1 97.08(17) . . ?
C6 B2 C5 117.2(2) . . ?
C6 B2 C14 113.0(2) . . ?
C14 B2 C5 99.56(18) . . ?

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
N1 C12 C13 C6 -0.8(3) . . . . ?
N1 C12 C13 C26 179.7(2) . . . . ?
N1 C24 C25 C10 -0.2(4) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 C15 -179.9(2) . . . . ?
C3 C2 C21 C20 -1.2(4) . . . . ?
C3 C2 C27 F3 7.3(11) . . . . ?
C3 C2 C27 F1 -113.7(6) . . . . ?
C3 C2 C27 F2 130.1(6) . . . . ?
C3 C2 C27 F1A 142.7(8) . . . . ?
C3 C2 C27 F2A 23.8(13) . . . . ?
C3 C2 C27 F3A -93.2(15) . . . . ?
C3 C4 C5 C20 -2.7(3) . . . . ?
C3 C4 C5 B2 176.2(2) . . . . ?
C3 C4 C15 C14 -177.4(2) . . . . ?
C3 C4 C15 C16 3.8(4) . . . . ?
C4 C5 C20 C21 3.2(3) . . . . ?
C4 C5 B2 N1 126.4(2) . . . . ?
C4 C5 B2 C6 -118.9(2) . . . . ?
C4 C5 B2 C14 3.2(2) . . . . ?
C4 C15 C16 C17 177.3(2) . . . . ?
C5 C4 C15 C14 2.3(2) . . . . ?
C5 C4 C15 C16 -176.4(2) . . . . ?
C5 C20 C21 C2 -1.3(4) . . . . ?
C6 C7 C8 C9 -0.2(5) . . . . ?
C6 C13 C26 C9 0.2(4) . . . . ?
C7 C6 C13 C12 -179.4(2) . . . . ?
C7 C6 C13 C26 0.2(4) . . . . ?
C7 C6 B2 N1 179.0(3) . . . . ?
C7 C6 B2 C5 53.7(4) . . . . ?
C7 C6 B2 C14 -61.2(3) . . . . ?
C7 C8 C9 C26 0.5(5) . . . . ?
C8 C9 C26 C13 -0.5(4) . . . . ?
C10 C11 C12 N1 1.0(4) . . . . ?
C10 C11 C12 C13 -179.2(2) . . . . ?
C11 C10 C25 C24 -0.1(4) . . . . ?
C11 C12 C13 C6 179.4(2) . . . . ?
C11 C12 C13 C26 -0.1(4) . . . . ?
C12 N1 C24 C25 0.9(4) . . . . ?
C12 N1 B2 C5 129.5(2) . . . . ?
C12 N1 B2 C6 4.0(2) . . . . ?
C12 N1 B2 C14 -115.1(2) . . . . ?
C12 C13 C26 C9 179.6(2) . . . . ?
C13 C6 C7 C8 -0.2(4) . . . . ?
C13 C6 B2 N1 -4.4(2) . . . . ?
C13 C6 B2 C5 -129.7(2) . . . . ?
C13 C6 B2 C14 115.4(2) . . . . ?
C14 C15 C16 C17 -1.3(3) . . . . ?
C15 C4 C5 C20 177.52(19) . . . . ?
C15 C4 C5 B2 -3.6(2) . . . . ?
C15 C14 C19 C18 3.4(3) . . . . ?
C15 C14 B2 N1 -127.2(2) . . . . ?
C15 C14 B2 C5 -1.9(2) . . . . ?
C15 C14 B2 C6 123.3(2) . . . . ?
C15 C16 C17 C18 2.2(4) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C17 C18 C19 C14 -2.5(4) . . . . ?
C19 C14 C15 C4 179.7(2) . . . . ?
C19 C14 C15 C16 -1.4(3) . . . . ?
C19 C14 B2 N1 53.1(4) . . . . ?
C19 C14 B2 C5 178.4(2) . . . . ?
C19 C14 B2 C6 -56.4(3) . . . . ?
C20 C5 B2 N1 -54.9(3) . . . . ?
C20 C5 B2 C6 59.8(3) . . . . ?
C20 C5 B2 C14 -178.0(2) . . . . ?
C21 C2 C3 C4 1.6(3) . . . . ?
C21 C2 C27 F3 -173.6(10) . . . . ?
C21 C2 C27 F1 65.5(6) . . . . ?
C21 C2 C27 F2 -50.8(7) . . . . ?
C21 C2 C27 F1A -38.1(9) . . . . ?
C21 C2 C27 F2A -157.0(12) . . . . ?
C21 C2 C27 F3A 86.0(15) . . . . ?
C24 N1 C12 C11 -1.3(4) . . . . ?
C24 N1 C12 C13 178.9(2) . . . . ?
C24 N1 B2 C5 -51.9(4) . . . . ?
C24 N1 B2 C6 -177.4(2) . . . . ?
C24 N1 B2 C14 63.6(3) . . . . ?
C25 C10 C11 C12 -0.3(4) . . . . ?
C27 C2 C3 C4 -179.2(2) . . . . ?
C27 C2 C21 C20 179.7(2) . . . . ?
B2 N1 C12 C11 177.5(2) . . . . ?
B2 N1 C12 C13 -2.3(3) . . . . ?
B2 N1 C24 C25 -177.7(3) . . . . ?
B2 C5 C20 C21 -175.4(2) . . . . ?
B2 C6 C7 C8 176.2(3) . . . . ?
B2 C6 C13 C12 3.6(3) . . . . ?
B2 C6 C13 C26 -176.9(2) . . . . ?
B2 C14 C15 C4 0.0(2) . . . . ?
B2 C14 C15 C16 178.8(2) . . . . ?
B2 C14 C19 C18 -177.0(2) . . . . ?

_olex2_exptl_crystal_mounting_method cryoroop
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_220228_ysg_hashizume_01_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2203028'
loop_
_audit_author_name
_audit_author_address
'Yusuke Yoshigoe'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-08-23 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-02-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 B N O'
_chemical_formula_sum            'C24 H18 B N O'
_chemical_formula_weight         347.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.929(2)
_cell_length_b                   9.6055(19)
_cell_length_c                   15.347(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.252(4)
_cell_angle_gamma                90
_cell_volume                     1810.1(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4830
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.849
_cell_measurement_theta_min      2.539
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.998
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.2824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1286 before and 0.0767 after correction.
The Ratio of minimum to maximum transmission is 0.3785.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_preparation       diffusion
_exptl_crystal_recrystallization_method diffusion
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.730
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15581
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.730
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.814
_diffrn_reflns_theta_min         2.539
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.730
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_special_details          none
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2723
_reflns_number_total             4144
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4144
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0665
_refine_ls_restrained_S_all      1.086
_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)+(0.1048P)²+0.1085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.1929
_refine_special_details          none
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 N1, C26, C22
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C26, N1, C22
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C2(H2), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
3.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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
N1 N 0.31751(14) 0.56032(18) 0.52058(12) 0.0349(4) Uani 1 1 d . . . . .
O1 O 0.02392(13) 0.17010(16) 0.72215(10) 0.0421(4) Uani 1 1 d . . . . .
C3 C 0.22847(15) 0.7349(2) 0.58337(12) 0.0269(4) Uani 1 1 d . . . . .
C24 C 0.36742(19) 0.5595(2) 0.35790(16) 0.0401(5) Uani 1 1 d . . . . .
H24 H 0.385340 0.558679 0.303757 0.048 Uiso 1 1 calc R U . . .
C2 C 0.32288(17) 0.6765(2) 0.38280(14) 0.0337(5) Uani 1 1 d . . . . .
H2 H 0.310433 0.755589 0.346057 0.040 Uiso 1 1 calc R U . . .
C26 C 0.29656(16) 0.6747(2) 0.46428(13) 0.0298(4) Uani 1 1 d . . . . .
C4 C 0.20179(16) 0.4637(2) 0.62791(13) 0.0281(4) Uani 1 1 d . . . . .
C5 C 0.10612(16) 0.4034(2) 0.57125(13) 0.0293(4) Uani 1 1 d . . . . .
H5 H 0.079789 0.429552 0.509905 0.035 Uiso 1 1 calc R U . . .
C6 C 0.04979(17) 0.3055(2) 0.60452(14) 0.0336(5) Uani 1 1 d . . . . .
H6 H -0.013798 0.266630 0.565578 0.040 Uiso 1 1 calc R U . . .
C7 C 0.08788(17) 0.2649(2) 0.69620(13) 0.0320(5) Uani 1 1 d . . . . .
C8 C 0.0590(2) 0.1233(3) 0.81500(15) 0.0447(6) Uani 1 1 d . . . . .
H8A H 0.127830 0.076717 0.827639 0.067 Uiso 1 1 calc R U . . .
H8B H 0.006116 0.059971 0.824540 0.067 Uiso 1 1 calc R U . . .
H8C H 0.066666 0.201692 0.855332 0.067 Uiso 1 1 calc R U . . .
C9 C 0.24184(16) 0.4164(2) 0.71900(13) 0.0282(4) Uani 1 1 d . . . . .
C10 C 0.34829(16) 0.4830(2) 0.76650(13) 0.0287(4) Uani 1 1 d . . . . .
C11 C 0.37610(16) 0.5795(2) 0.70829(13) 0.0298(5) Uani 1 1 d . . . . .
C12 C 0.47345(17) 0.6529(2) 0.74204(14) 0.0339(5) Uani 1 1 d . . . . .
H12 H 0.491502 0.720136 0.705643 0.041 Uiso 1 1 calc R U . . .
C13 C 0.54433(17) 0.6264(2) 0.83026(14) 0.0357(5) Uani 1 1 d . . . . .
H13 H 0.610326 0.673558 0.851388 0.043 Uiso 1 1 calc R U . . .
C14 C 0.51624(18) 0.5301(2) 0.88599(14) 0.0366(5) Uani 1 1 d . . . . .
H14 H 0.563952 0.512343 0.944309 0.044 Uiso 1 1 calc R U . . .
C15 C 0.41722(17) 0.4595(2) 0.85573(14) 0.0330(5) Uani 1 1 d . . . . .
H15 H 0.397291 0.397656 0.894285 0.040 Uiso 1 1 calc R U . . .
C16 C 0.24342(15) 0.7825(2) 0.50239(13) 0.0306(5) Uani 1 1 d . . . . .
C17 C 0.17513(18) 0.8210(2) 0.62737(15) 0.0404(5) Uani 1 1 d . . . . .
H17 H 0.163316 0.790421 0.680976 0.048 Uiso 1 1 calc R U . . .
C18 C 0.13924(19) 0.9503(2) 0.59375(17) 0.0450(6) Uani 1 1 d . . . . .
H18 H 0.103863 1.006786 0.624682 0.054 Uiso 1 1 calc R U . . .
C19 C 0.15571(19) 0.9974(2) 0.51314(16) 0.0422(6) Uani 1 1 d . . . . .
H19 H 0.131770 1.085646 0.490783 0.051 Uiso 1 1 calc R U . . .
C20 C 0.20730(17) 0.9139(2) 0.46639(15) 0.0353(5) Uani 1 1 d . . . . .
H20 H 0.217812 0.944285 0.412244 0.042 Uiso 1 1 calc R U . . .
C21 C 0.38582(19) 0.4419(2) 0.41367(17) 0.0418(6) Uani 1 1 d . . . . .
H21 H 0.414534 0.361726 0.396159 0.050 Uiso 1 1 calc R U . . .
C22 C 0.36144(18) 0.4444(2) 0.49480(16) 0.0381(5) Uani 1 1 d . . . . .
H22 H 0.375068 0.366152 0.532421 0.046 Uiso 1 1 calc R U . . .
C23 C 0.18616(17) 0.3182(2) 0.75448(13) 0.0313(5) Uani 1 1 d . . . . .
H23 H 0.213547 0.289031 0.815161 0.038 Uiso 1 1 calc R U . . .
B1 B 0.28033(19) 0.5827(2) 0.61005(15) 0.0316(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
N1 C26 1.371(3) . ?
N1 C22 1.364(3) . ?
N1 B1 1.605(3) . ?
O1 C7 1.370(3) . ?
O1 C8 1.426(3) . ?
C3 C16 1.393(3) . ?
C3 C17 1.381(3) . ?
C3 B1 1.607(3) . ?
C24 H24 0.9300 . ?
C24 C2 1.370(3) . ?
C24 C21 1.392(3) . ?
C2 H2 0.9300 . ?
C2 C26 1.395(3) . ?
C26 C16 1.462(3) . ?
C4 C5 1.396(3) . ?
C4 C9 1.405(3) . ?
C4 B1 1.609(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.393(3) . ?
C7 C23 1.402(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.485(3) . ?
C9 C23 1.396(3) . ?
C10 C11 1.410(3) . ?
C10 C15 1.399(3) . ?
C11 C12 1.394(3) . ?
C11 B1 1.624(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.400(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.394(3) . ?
C15 H15 0.9300 . ?
C16 C20 1.398(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.395(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.377(3) . ?
C22 H22 0.9300 . ?
C23 H23 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 N1 B1 112.25(17) . . ?
C22 N1 C26 119.31(19) . . ?
C22 N1 B1 128.39(18) . . ?
C7 O1 C8 117.90(17) . . ?
C16 C3 B1 111.23(17) . . ?
C17 C3 C16 118.06(19) . . ?
C17 C3 B1 130.71(18) . . ?
C2 C24 H24 120.0 . . ?
C2 C24 C21 120.0(2) . . ?
C21 C24 H24 120.0 . . ?
C24 C2 H2 120.6 . . ?
C24 C2 C26 118.8(2) . . ?
C26 C2 H2 120.6 . . ?
N1 C26 C2 121.27(19) . . ?
N1 C26 C16 109.89(17) . . ?
C2 C26 C16 128.82(19) . . ?
C5 C4 C9 117.66(18) . . ?
C5 C4 B1 132.26(17) . . ?
C9 C4 B1 110.08(17) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.28(18) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.24(18) . . ?
C7 C6 H6 119.9 . . ?
O1 C7 C6 115.16(17) . . ?
O1 C7 C23 124.50(18) . . ?
C6 C7 C23 120.32(19) . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 C10 110.20(17) . . ?
C23 C9 C4 122.12(17) . . ?
C23 C9 C10 127.66(17) . . ?
C11 C10 C9 110.66(16) . . ?
C15 C10 C9 128.28(19) . . ?
C15 C10 C11 121.05(19) . . ?
C10 C11 B1 109.24(17) . . ?
C12 C11 C10 118.51(17) . . ?
C12 C11 B1 132.25(19) . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.73(19) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 120.5 . . ?
C14 C15 C10 119.0(2) . . ?
C14 C15 H15 120.5 . . ?
C3 C16 C26 109.79(18) . . ?
C3 C16 C20 121.7(2) . . ?
C20 C16 C26 128.46(19) . . ?
C3 C17 H17 119.3 . . ?
C18 C17 C3 121.4(2) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C16 C20 H20 120.8 . . ?
C19 C20 C16 118.4(2) . . ?
C19 C20 H20 120.8 . . ?
C24 C21 H21 120.1 . . ?
C22 C21 C24 119.9(2) . . ?
C22 C21 H21 120.1 . . ?
N1 C22 C21 120.7(2) . . ?
N1 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C7 C23 H23 120.9 . . ?
C9 C23 C7 118.24(17) . . ?
C9 C23 H23 120.9 . . ?
N1 B1 C3 96.71(15) . . ?
N1 B1 C4 115.12(17) . . ?
N1 B1 C11 116.49(18) . . ?
C3 B1 C4 117.05(18) . . ?
C3 B1 C11 112.96(16) . . ?
C4 B1 C11 99.58(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
N1 C26 C16 C3 -1.1(2) . . . . ?
N1 C26 C16 C20 -179.20(18) . . . . ?
O1 C7 C23 C9 -178.81(19) . . . . ?
C3 C16 C20 C19 0.0(3) . . . . ?
C3 C17 C18 C19 0.4(3) . . . . ?
C24 C2 C26 N1 2.0(3) . . . . ?
C24 C2 C26 C16 -176.3(2) . . . . ?
C24 C21 C22 N1 1.2(3) . . . . ?
C2 C24 C21 C22 -1.4(3) . . . . ?
C2 C26 C16 C3 177.4(2) . . . . ?
C2 C26 C16 C20 -0.7(3) . . . . ?
C26 N1 C22 C21 0.7(3) . . . . ?
C26 N1 B1 C3 3.0(2) . . . . ?
C26 N1 B1 C4 127.09(18) . . . . ?
C26 N1 B1 C11 -116.87(19) . . . . ?
C26 C16 C20 C19 177.89(19) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C4 C9 C10 C11 2.9(2) . . . . ?
C4 C9 C10 C15 -176.7(2) . . . . ?
C4 C9 C23 C7 0.7(3) . . . . ?
C5 C4 C9 C10 175.22(17) . . . . ?
C5 C4 C9 C23 -3.4(3) . . . . ?
C5 C4 B1 N1 -50.1(3) . . . . ?
C5 C4 B1 C3 62.5(3) . . . . ?
C5 C4 B1 C11 -175.5(2) . . . . ?
C5 C6 C7 O1 178.30(18) . . . . ?
C5 C6 C7 C23 -2.8(3) . . . . ?
C6 C7 C23 C9 2.4(3) . . . . ?
C8 O1 C7 C6 179.43(19) . . . . ?
C8 O1 C7 C23 0.6(3) . . . . ?
C9 C4 C5 C6 3.1(3) . . . . ?
C9 C4 B1 N1 129.96(18) . . . . ?
C9 C4 B1 C3 -117.44(19) . . . . ?
C9 C4 B1 C11 4.6(2) . . . . ?
C9 C10 C11 C12 179.43(18) . . . . ?
C9 C10 C11 B1 0.3(2) . . . . ?
C9 C10 C15 C14 177.69(19) . . . . ?
C10 C9 C23 C7 -177.68(19) . . . . ?
C10 C11 C12 C13 3.0(3) . . . . ?
C10 C11 B1 N1 -127.23(19) . . . . ?
C10 C11 B1 C3 122.11(19) . . . . ?
C10 C11 B1 C4 -2.8(2) . . . . ?
C11 C10 C15 C14 -1.9(3) . . . . ?
C11 C12 C13 C14 -2.3(3) . . . . ?
C12 C11 B1 N1 53.8(3) . . . . ?
C12 C11 B1 C3 -56.9(3) . . . . ?
C12 C11 B1 C4 178.2(2) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C10 2.6(3) . . . . ?
C15 C10 C11 C12 -0.9(3) . . . . ?
C15 C10 C11 B1 179.89(18) . . . . ?
C16 C3 C17 C18 -1.1(3) . . . . ?
C16 C3 B1 N1 -3.6(2) . . . . ?
C16 C3 B1 C4 -126.31(19) . . . . ?
C16 C3 B1 C11 118.90(19) . . . . ?
C17 C3 C16 C26 -177.37(17) . . . . ?
C17 C3 C16 C20 0.9(3) . . . . ?
C17 C3 B1 N1 177.06(19) . . . . ?
C17 C3 B1 C4 54.4(3) . . . . ?
C17 C3 B1 C11 -60.4(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C16 -0.7(3) . . . . ?
C21 C24 C2 C26 -0.1(3) . . . . ?
C22 N1 C26 C2 -2.3(3) . . . . ?
C22 N1 C26 C16 176.30(17) . . . . ?
C22 N1 B1 C3 -174.52(19) . . . . ?
C22 N1 B1 C4 -50.4(3) . . . . ?
C22 N1 B1 C11 65.6(3) . . . . ?
C23 C9 C10 C11 -178.5(2) . . . . ?
C23 C9 C10 C15 1.9(3) . . . . ?
B1 N1 C26 C2 179.94(18) . . . . ?
B1 N1 C26 C16 -1.4(2) . . . . ?
B1 N1 C22 C21 178.0(2) . . . . ?
B1 C3 C16 C26 3.2(2) . . . . ?
B1 C3 C16 C20 -178.56(17) . . . . ?
B1 C3 C17 C18 178.2(2) . . . . ?
B1 C4 C5 C6 -176.9(2) . . . . ?
B1 C4 C9 C10 -4.8(2) . . . . ?
B1 C4 C9 C23 176.49(19) . . . . ?
B1 C11 C12 C13 -178.0(2) . . . . ?

_olex2_exptl_crystal_mounting_method cryoroop
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_211006_ysg_hashizume_02_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2203030'
loop_
_audit_author_name
_audit_author_address
'Yusuke Yoshigoe'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-08-23 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_audit_creation_date             2021-10-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C24 H18 B N O)'
_chemical_formula_sum            'C48 H36 B2 N2 O2'
_chemical_formula_weight         694.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.9380(5)
_cell_length_b                   12.7143(5)
_cell_length_c                   14.2807(6)
_cell_angle_alpha                109.1900(10)
_cell_angle_beta                 103.359(2)
_cell_angle_gamma                108.8850(10)
_cell_volume                     1793.52(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      31.03
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6960
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1285 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.9327.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 1.00 1.00 0.0520
0.00 0.00 -1.00 0.1110
0.00 0.00 1.00 0.1340
1.00 0.00 1.00 0.1020
1.00 -1.00 1.00 0.1940
1.00 1.00 1.00 0.1190
0.00 1.00 0.00 0.1560
0.00 -1.00 0.00 0.2370
-1.00 -1.00 0.00 0.1990
1.00 0.00 0.00 0.1720
-1.00 0.00 0.00 0.1300
-1.00 1.00 0.00 0.0210
1.00 -1.00 0.00 0.1720
-1.00 -1.00 1.00 0.2510
-1.00 0.00 1.00 0.2010
0.00 -1.00 1.00 0.2680
-1.00 -1.00 -1.00 0.1900

_exptl_crystal_size_max          0.577
_exptl_crystal_size_mid          0.349
_exptl_crystal_size_min          0.258
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1616
_diffrn_reflns_av_unetI/netI     0.1262
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.780
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41838
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.481
_diffrn_reflns_theta_min         1.875
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.780
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6084
_reflns_number_total             9289
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         9289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0808P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1426
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27), C30(H30), C33(H33), C34(H34), C38(H38), C41(H41),
 C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C32(H32A,H32B,H32C)
;
_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
O1 O 0.04903(12) 1.03494(10) 0.14014(10) 0.0320(3) Uani 1 1 d . . . . .
O2 O 0.49224(12) 0.65495(9) 0.43488(9) 0.0259(2) Uani 1 1 d . . . . .
N1 N 0.28627(12) 0.79387(9) 0.32538(9) 0.0164(2) Uani 1 1 d . . . . .
N2 N 0.39578(12) 0.56427(9) 0.78221(9) 0.0173(2) Uani 1 1 d . . . . .
C1 C -0.06929(19) 0.93729(16) 0.11625(17) 0.0370(4) Uani 1 1 d . . . . .
H1A H -0.084152 0.864293 0.056645 0.055 Uiso 1 1 calc R U . . .
H1B H -0.137166 0.960774 0.098468 0.055 Uiso 1 1 calc R U . . .
H1C H -0.066544 0.920780 0.177479 0.055 Uiso 1 1 calc R U . . .
C2 C 0.15414(16) 1.01127(12) 0.15715(12) 0.0237(3) Uani 1 1 d . . . . .
C3 C 0.15725(15) 0.90870(11) 0.17271(11) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.084431 0.851032 0.171426 0.023 Uiso 1 1 calc R U . . .
C4 C 0.26872(14) 0.89330(11) 0.18997(11) 0.0167(3) Uani 1 1 d . . . . .
C5 C 0.21449(14) 0.68050(11) 0.31569(11) 0.0160(3) Uani 1 1 d . . . . .
C6 C 0.19172(14) 0.66781(11) 0.40384(11) 0.0184(3) Uani 1 1 d . . . . .
H6 H 0.142691 0.590455 0.397725 0.022 Uiso 1 1 calc R U . . .
C7 C 0.24277(15) 0.77126(11) 0.49984(12) 0.0197(3) Uani 1 1 d . . . . .
H7 H 0.228805 0.764094 0.559350 0.024 Uiso 1 1 calc R U . . .
C8 C 0.21712(14) 0.64328(11) 0.14334(11) 0.0160(3) Uani 1 1 d . . . . .
C9 C 0.17298(13) 0.58818(11) 0.20628(11) 0.0159(3) Uani 1 1 d . . . . .
C10 C 0.09957(14) 0.46105(11) 0.16624(12) 0.0194(3) Uani 1 1 d . . . . .
H10 H 0.071806 0.427211 0.209969 0.023 Uiso 1 1 calc R U . . .
C11 C 0.06933(15) 0.38693(11) 0.05993(12) 0.0209(3) Uani 1 1 d . . . . .
H11 H 0.020078 0.302083 0.031259 0.025 Uiso 1 1 calc R U . . .
C12 C 0.11227(15) 0.43872(11) -0.00450(12) 0.0207(3) Uani 1 1 d . . . . .
H12 H 0.091601 0.387805 -0.075850 0.025 Uiso 1 1 calc R U . . .
C13 C 0.18590(14) 0.56594(11) 0.03638(11) 0.0191(3) Uani 1 1 d . . . . .
H13 H 0.214104 0.599113 -0.007569 0.023 Uiso 1 1 calc R U . . .
C14 C 0.31565(15) 0.88718(12) 0.50799(12) 0.0206(3) Uani 1 1 d . . . . .
H14 H 0.349947 0.957759 0.572425 0.025 Uiso 1 1 calc R U . . .
C15 C 0.33570(15) 0.89494(11) 0.41901(12) 0.0200(3) Uani 1 1 d . . . . .
H15 H 0.384410 0.971639 0.423764 0.024 Uiso 1 1 calc R U . . .
C16 C 0.45271(14) 0.84256(11) 0.23122(11) 0.0167(3) Uani 1 1 d . . . . .
C17 C 0.54440(15) 0.80150(11) 0.25667(12) 0.0207(3) Uani 1 1 d . . . . .
H17 H 0.522993 0.731452 0.268934 0.025 Uiso 1 1 calc R U . . .
C18 C 0.66897(16) 0.86398(13) 0.26422(12) 0.0241(3) Uani 1 1 d . . . . .
H18 H 0.730109 0.836026 0.281980 0.029 Uiso 1 1 calc R U . . .
C19 C 0.70082(15) 0.96824(12) 0.24496(12) 0.0246(3) Uani 1 1 d . . . . .
H19 H 0.783315 1.009034 0.249075 0.030 Uiso 1 1 calc R U . . .
C20 C 0.61083(15) 1.01238(12) 0.21961(12) 0.0211(3) Uani 1 1 d . . . . .
H20 H 0.632656 1.081926 0.206642 0.025 Uiso 1 1 calc R U . . .
C21 C 0.48725(14) 0.95039(11) 0.21399(11) 0.0183(3) Uani 1 1 d . . . . .
C22 C 0.37891(14) 0.98130(11) 0.19242(11) 0.0174(3) Uani 1 1 d . . . . .
C23 C 0.37545(16) 1.08356(11) 0.17659(12) 0.0235(3) Uani 1 1 d . . . . .
H23 H 0.447954 1.141398 0.177643 0.028 Uiso 1 1 calc R U . . .
C24 C 0.26311(17) 1.09794(12) 0.15933(12) 0.0250(3) Uani 1 1 d . . . . .
H24 H 0.260652 1.165877 0.149174 0.030 Uiso 1 1 calc R U . . .
C25 C 0.19379(16) 0.81667(12) 0.88501(13) 0.0238(3) Uani 1 1 d . . . . .
H25 H 0.178880 0.876011 0.932323 0.029 Uiso 1 1 calc R U . . .
C26 C 0.11543(16) 0.75503(12) 0.77671(13) 0.0240(3) Uani 1 1 d . . . . .
H26 H 0.049383 0.774712 0.752157 0.029 Uiso 1 1 calc R U . . .
C27 C 0.13471(14) 0.66395(11) 0.70440(12) 0.0205(3) Uani 1 1 d . . . . .
H27 H 0.081489 0.623665 0.632383 0.025 Uiso 1 1 calc R U . . .
C28 C 0.23281(14) 0.63335(11) 0.73953(11) 0.0173(3) Uani 1 1 d . . . . .
C29 C 0.30857(14) 0.52116(11) 0.57610(11) 0.0174(3) Uani 1 1 d . . . . .
C30 C 0.39919(14) 0.60775(11) 0.56024(11) 0.0185(3) Uani 1 1 d . . . . .
H30 H 0.453250 0.685878 0.616006 0.022 Uiso 1 1 calc R U . . .
C31 C 0.40803(15) 0.57611(12) 0.45991(12) 0.0199(3) Uani 1 1 d . . . . .
C32 C 0.58030(17) 0.77377(12) 0.51886(13) 0.0269(3) Uani 1 1 d . . . . .
H32A H 0.534181 0.818026 0.545574 0.040 Uiso 1 1 calc R U . . .
H32B H 0.635017 0.818919 0.491980 0.040 Uiso 1 1 calc R U . . .
H32C H 0.631106 0.764557 0.575704 0.040 Uiso 1 1 calc R U . . .
C33 C 0.32735(15) 0.45941(13) 0.37566(12) 0.0226(3) Uani 1 1 d . . . . .
H33 H 0.333603 0.440073 0.308930 0.027 Uiso 1 1 calc R U . . .
C34 C 0.23780(15) 0.37203(12) 0.39092(12) 0.0214(3) Uani 1 1 d . . . . .
H34 H 0.184153 0.294028 0.334831 0.026 Uiso 1 1 calc R U . . .
C35 C 0.22898(14) 0.40231(11) 0.49129(11) 0.0192(3) Uani 1 1 d . . . . .
C36 C 0.14715(15) 0.32245(11) 0.52669(12) 0.0195(3) Uani 1 1 d . . . . .
C37 C 0.17062(14) 0.38720(11) 0.63593(12) 0.0192(3) Uani 1 1 d . . . . .
C38 C 0.29365(16) 0.78983(11) 0.92229(12) 0.0214(3) Uani 1 1 d . . . . .
H38 H 0.347355 0.831399 0.994219 0.026 Uiso 1 1 calc R U . . .
C39 C 0.31192(14) 0.69868(11) 0.84924(11) 0.0175(3) Uani 1 1 d . . . . .
C40 C 0.41020(15) 0.65616(11) 0.87353(11) 0.0175(3) Uani 1 1 d . . . . .
C41 C 0.50736(16) 0.69487(12) 0.96969(12) 0.0237(3) Uani 1 1 d . . . . .
H41 H 0.517009 0.757092 1.032182 0.028 Uiso 1 1 calc R U . . .
C42 C 0.58955(17) 0.63944(13) 0.97107(13) 0.0272(3) Uani 1 1 d . . . . .
H42 H 0.654932 0.663922 1.034921 0.033 Uiso 1 1 calc R U . . .
C43 C 0.57442(16) 0.54673(13) 0.87664(13) 0.0257(3) Uani 1 1 d . . . . .
H43 H 0.629866 0.509498 0.876651 0.031 Uiso 1 1 calc R U . . .
C44 C 0.47601(15) 0.51125(12) 0.78339(12) 0.0210(3) Uani 1 1 d . . . . .
H44 H 0.465121 0.449340 0.720113 0.025 Uiso 1 1 calc R U . . .
C45 C 0.10580(16) 0.32523(13) 0.68459(13) 0.0248(3) Uani 1 1 d . . . . .
H45 H 0.120669 0.366875 0.756547 0.030 Uiso 1 1 calc R U . . .
C46 C 0.01792(16) 0.20025(13) 0.62639(14) 0.0284(3) Uani 1 1 d . . . . .
H46 H -0.024656 0.159015 0.659799 0.034 Uiso 1 1 calc R U . . .
C47 C -0.00524(15) 0.13844(12) 0.51898(14) 0.0280(3) Uani 1 1 d . . . . .
H47 H -0.064596 0.055921 0.480251 0.034 Uiso 1 1 calc R U . . .
C48 C 0.05912(16) 0.19823(12) 0.46841(13) 0.0251(3) Uani 1 1 d . . . . .
H48 H 0.043725 0.155926 0.396428 0.030 Uiso 1 1 calc R U . . .
B1 B 0.30296(16) 0.78953(12) 0.21594(13) 0.0170(3) Uani 1 1 d . . . . .
B2 B 0.27477(17) 0.52911(13) 0.68079(13) 0.0178(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.420(2) . ?
O1 C2 1.3696(19) . ?
O2 C31 1.3757(16) . ?
O2 C32 1.4227(19) . ?
N1 C5 1.3586(14) . ?
N1 C15 1.3426(18) . ?
N1 B1 1.6061(19) . ?
N2 C40 1.3636(17) . ?
N2 C44 1.3380(17) . ?
N2 B2 1.604(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.4034(17) . ?
C2 C24 1.392(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(2) . ?
C4 C22 1.4084(18) . ?
C4 B1 1.6267(18) . ?
C5 C6 1.3956(18) . ?
C5 C9 1.4575(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.3750(19) . ?
C7 H7 0.9300 . ?
C7 C14 1.3974(17) . ?
C8 C9 1.4036(17) . ?
C8 C13 1.3969(19) . ?
C8 B1 1.6096(18) . ?
C9 C10 1.3970(16) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.3932(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.3969(17) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.3745(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(2) . ?
C16 C21 1.4188(16) . ?
C16 B1 1.625(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.400(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.3926(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.394(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.398(2) . ?
C21 C22 1.465(2) . ?
C22 C23 1.4025(16) . ?
C23 H23 0.9300 . ?
C23 C24 1.389(2) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.393(2) . ?
C25 C38 1.382(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.399(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.388(2) . ?
C28 C39 1.410(2) . ?
C28 B2 1.6137(19) . ?
C29 C30 1.3927(18) . ?
C29 C35 1.4102(19) . ?
C29 B2 1.617(2) . ?
C30 H30 0.9300 . ?
C30 C31 1.3944(19) . ?
C31 C33 1.394(2) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33 0.9300 . ?
C33 C34 1.387(2) . ?
C34 H34 0.9300 . ?
C34 C35 1.395(2) . ?
C35 C36 1.4713(19) . ?
C36 C37 1.412(2) . ?
C36 C48 1.3960(19) . ?
C37 C45 1.3843(19) . ?
C37 B2 1.622(2) . ?
C38 H38 0.9300 . ?
C38 C39 1.3975(18) . ?
C39 C40 1.461(2) . ?
C40 C41 1.387(2) . ?
C41 H41 0.9300 . ?
C41 C42 1.381(2) . ?
C42 H42 0.9300 . ?
C42 C43 1.395(2) . ?
C43 H43 0.9300 . ?
C43 C44 1.377(2) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C45 C46 1.402(2) . ?
C46 H46 0.9300 . ?
C46 C47 1.385(2) . ?
C47 H47 0.9300 . ?
C47 C48 1.389(2) . ?
C48 H48 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
C2 O1 C1 116.62(10) . . ?
C31 O2 C32 117.39(11) . . ?
C5 N1 B1 112.74(10) . . ?
C15 N1 C5 120.86(11) . . ?
C15 N1 B1 126.40(10) . . ?
C40 N2 B2 112.81(11) . . ?
C44 N2 C40 120.72(13) . . ?
C44 N2 B2 126.46(12) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.40(14) . . ?
O1 C2 C24 115.49(11) . . ?
C24 C2 C3 120.11(14) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.04(13) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C22 119.73(11) . . ?
C3 C4 B1 131.10(12) . . ?
C22 C4 B1 109.09(12) . . ?
N1 C5 C6 120.04(12) . . ?
N1 C5 C9 109.38(11) . . ?
C6 C5 C9 130.58(11) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.09(11) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C14 120.00(12) . . ?
C14 C7 H7 120.0 . . ?
C9 C8 B1 109.62(11) . . ?
C13 C8 C9 117.64(10) . . ?
C13 C8 B1 132.67(11) . . ?
C8 C9 C5 111.02(10) . . ?
C10 C9 C5 126.11(11) . . ?
C10 C9 C8 122.87(12) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.22(12) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.30(11) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.03(13) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 119.93(12) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C7 C14 H14 120.6 . . ?
C15 C14 C7 118.78(13) . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 121.23(11) . . ?
N1 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C21 118.89(13) . . ?
C17 C16 B1 131.81(11) . . ?
C21 C16 B1 109.29(12) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.87(12) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.60(14) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 120.96(14) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 118.94(12) . . ?
C21 C20 H20 120.5 . . ?
C16 C21 C22 110.53(12) . . ?
C20 C21 C16 120.71(13) . . ?
C20 C21 C22 128.76(11) . . ?
C4 C22 C21 111.57(10) . . ?
C23 C22 C4 120.12(14) . . ?
C23 C22 C21 128.31(13) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.60(13) . . ?
C24 C23 H23 120.2 . . ?
C2 C24 H24 119.8 . . ?
C23 C24 C2 120.41(11) . . ?
C23 C24 H24 119.8 . . ?
C26 C25 H25 119.9 . . ?
C38 C25 H25 119.9 . . ?
C38 C25 C26 120.15(13) . . ?
C25 C26 H26 119.5 . . ?
C25 C26 C27 120.92(14) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.38(14) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C39 117.46(12) . . ?
C27 C28 B2 132.98(13) . . ?
C39 C28 B2 109.46(12) . . ?
C30 C29 C35 119.62(12) . . ?
C30 C29 B2 131.22(12) . . ?
C35 C29 B2 109.16(11) . . ?
C29 C30 H30 120.3 . . ?
C29 C30 C31 119.33(13) . . ?
C31 C30 H30 120.3 . . ?
O2 C31 C30 124.19(13) . . ?
O2 C31 C33 114.93(12) . . ?
C33 C31 C30 120.86(13) . . ?
O2 C32 H32A 109.5 . . ?
O2 C32 H32B 109.5 . . ?
O2 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33 119.9 . . ?
C34 C33 C31 120.28(13) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 120.3 . . ?
C33 C34 C35 119.33(13) . . ?
C35 C34 H34 120.3 . . ?
C29 C35 C36 111.03(12) . . ?
C34 C35 C29 120.56(13) . . ?
C34 C35 C36 128.36(12) . . ?
C37 C36 C35 110.71(11) . . ?
C48 C36 C35 128.70(14) . . ?
C48 C36 C37 120.56(13) . . ?
C36 C37 B2 109.11(11) . . ?
C45 C37 C36 118.94(13) . . ?
C45 C37 B2 131.94(13) . . ?
C25 C38 H38 120.8 . . ?
C25 C38 C39 118.36(14) . . ?
C39 C38 H38 120.8 . . ?
C28 C39 C40 110.91(11) . . ?
C38 C39 C28 122.71(14) . . ?
C38 C39 C40 126.37(13) . . ?
N2 C40 C39 109.33(12) . . ?
N2 C40 C41 120.40(13) . . ?
C41 C40 C39 130.27(12) . . ?
C40 C41 H41 120.6 . . ?
C42 C41 C40 118.87(14) . . ?
C42 C41 H41 120.6 . . ?
C41 C42 H42 120.0 . . ?
C41 C42 C43 119.96(15) . . ?
C43 C42 H42 120.0 . . ?
C42 C43 H43 120.6 . . ?
C44 C43 C42 118.87(14) . . ?
C44 C43 H43 120.6 . . ?
N2 C44 C43 121.16(13) . . ?
N2 C44 H44 119.4 . . ?
C43 C44 H44 119.4 . . ?
C37 C45 H45 119.7 . . ?
C37 C45 C46 120.60(15) . . ?
C46 C45 H45 119.7 . . ?
C45 C46 H46 120.1 . . ?
C47 C46 C45 119.77(14) . . ?
C47 C46 H46 120.1 . . ?
C46 C47 H47 119.6 . . ?
C46 C47 C48 120.78(13) . . ?
C48 C47 H47 119.6 . . ?
C36 C48 H48 120.3 . . ?
C47 C48 C36 119.34(15) . . ?
C47 C48 H48 120.3 . . ?
N1 B1 C4 109.53(10) . . ?
N1 B1 C8 97.20(9) . . ?
N1 B1 C16 111.39(12) . . ?
C8 B1 C4 122.87(12) . . ?
C8 B1 C16 116.56(11) . . ?
C16 B1 C4 99.47(10) . . ?
N2 B2 C28 97.32(11) . . ?
N2 B2 C29 112.84(12) . . ?
N2 B2 C37 110.80(10) . . ?
C28 B2 C29 121.20(11) . . ?
C28 B2 C37 115.37(12) . . ?
C29 B2 C37 99.76(11) . . ?

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
O1 C2 C3 C4 -179.62(13) . . . . ?
O1 C2 C24 C23 179.65(14) . . . . ?
O2 C31 C33 C34 -179.65(13) . . . . ?
N1 C5 C6 C7 0.0(2) . . . . ?
N1 C5 C9 C8 -0.99(16) . . . . ?
N1 C5 C9 C10 178.76(14) . . . . ?
N2 C40 C41 C42 0.5(2) . . . . ?
C1 O1 C2 C3 -12.7(2) . . . . ?
C1 O1 C2 C24 167.81(15) . . . . ?
C2 C3 C4 C22 0.4(2) . . . . ?
C2 C3 C4 B1 176.57(14) . . . . ?
C3 C2 C24 C23 0.2(2) . . . . ?
C3 C4 C22 C21 178.70(12) . . . . ?
C3 C4 C22 C23 -0.5(2) . . . . ?
C3 C4 B1 N1 -60.04(19) . . . . ?
C3 C4 B1 C8 52.8(2) . . . . ?
C3 C4 B1 C16 -176.88(14) . . . . ?
C4 C22 C23 C24 0.5(2) . . . . ?
C5 N1 C15 C14 0.1(2) . . . . ?
C5 N1 B1 C4 130.27(12) . . . . ?
C5 N1 B1 C8 1.56(15) . . . . ?
C5 N1 B1 C16 -120.68(12) . . . . ?
C5 C6 C7 C14 0.4(2) . . . . ?
C5 C9 C10 C11 -179.81(14) . . . . ?
C6 C5 C9 C8 179.11(15) . . . . ?
C6 C5 C9 C10 -1.1(3) . . . . ?
C6 C7 C14 C15 -0.6(2) . . . . ?
C7 C14 C15 N1 0.3(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C5 C6 C7 179.93(14) . . . . ?
C9 C8 C13 C12 0.5(2) . . . . ?
C9 C8 B1 N1 -2.09(14) . . . . ?
C9 C8 B1 C4 -120.96(14) . . . . ?
C9 C8 B1 C16 116.22(13) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C11 C12 C13 C8 -0.2(2) . . . . ?
C13 C8 C9 C5 179.36(13) . . . . ?
C13 C8 C9 C10 -0.4(2) . . . . ?
C13 C8 B1 N1 -178.85(15) . . . . ?
C13 C8 B1 C4 62.3(2) . . . . ?
C13 C8 B1 C16 -60.5(2) . . . . ?
C15 N1 C5 C6 -0.3(2) . . . . ?
C15 N1 C5 C9 179.79(12) . . . . ?
C15 N1 B1 C4 -50.07(19) . . . . ?
C15 N1 B1 C8 -178.77(13) . . . . ?
C15 N1 B1 C16 58.98(17) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C16 C21 C22 C4 -2.56(16) . . . . ?
C16 C21 C22 C23 176.57(14) . . . . ?
C17 C16 C21 C20 1.8(2) . . . . ?
C17 C16 C21 C22 -177.70(12) . . . . ?
C17 C16 B1 N1 63.36(18) . . . . ?
C17 C16 B1 C4 178.78(14) . . . . ?
C17 C16 B1 C8 -46.9(2) . . . . ?
C17 C18 C19 C20 0.8(2) . . . . ?
C18 C19 C20 C21 0.2(2) . . . . ?
C19 C20 C21 C16 -1.5(2) . . . . ?
C19 C20 C21 C22 177.87(13) . . . . ?
C20 C21 C22 C4 178.02(14) . . . . ?
C20 C21 C22 C23 -2.9(2) . . . . ?
C21 C16 C17 C18 -0.7(2) . . . . ?
C21 C16 B1 N1 -116.56(11) . . . . ?
C21 C16 B1 C4 -1.14(14) . . . . ?
C21 C16 B1 C8 133.18(12) . . . . ?
C21 C22 C23 C24 -178.57(14) . . . . ?
C22 C4 B1 N1 116.49(12) . . . . ?
C22 C4 B1 C8 -130.71(13) . . . . ?
C22 C4 B1 C16 -0.36(14) . . . . ?
C22 C23 C24 C2 -0.3(2) . . . . ?
C24 C2 C3 C4 -0.2(2) . . . . ?
C25 C26 C27 C28 -0.04(19) . . . . ?
C25 C38 C39 C28 -0.02(18) . . . . ?
C25 C38 C39 C40 -178.89(12) . . . . ?
C26 C25 C38 C39 -1.05(19) . . . . ?
C26 C27 C28 C39 -0.99(17) . . . . ?
C26 C27 C28 B2 175.17(13) . . . . ?
C27 C28 C39 C38 1.04(18) . . . . ?
C27 C28 C39 C40 -179.94(11) . . . . ?
C27 C28 B2 N2 179.68(13) . . . . ?
C27 C28 B2 C29 57.3(2) . . . . ?
C27 C28 B2 C37 -63.12(18) . . . . ?
C28 C39 C40 N2 -0.45(14) . . . . ?
C28 C39 C40 C41 179.52(13) . . . . ?
C29 C30 C31 O2 178.78(13) . . . . ?
C29 C30 C31 C33 0.1(2) . . . . ?
C29 C35 C36 C37 0.25(17) . . . . ?
C29 C35 C36 C48 -177.61(14) . . . . ?
C30 C29 C35 C34 -1.8(2) . . . . ?
C30 C29 C35 C36 175.75(12) . . . . ?
C30 C29 B2 N2 -56.72(18) . . . . ?
C30 C29 B2 C28 57.9(2) . . . . ?
C30 C29 B2 C37 -174.32(14) . . . . ?
C30 C31 C33 C34 -0.9(2) . . . . ?
C31 C33 C34 C35 0.3(2) . . . . ?
C32 O2 C31 C30 3.6(2) . . . . ?
C32 O2 C31 C33 -177.65(13) . . . . ?
C33 C34 C35 C29 1.1(2) . . . . ?
C33 C34 C35 C36 -176.04(14) . . . . ?
C34 C35 C36 C37 177.62(14) . . . . ?
C34 C35 C36 C48 -0.2(2) . . . . ?
C35 C29 C30 C31 1.2(2) . . . . ?
C35 C29 B2 N2 122.24(12) . . . . ?
C35 C29 B2 C28 -123.13(14) . . . . ?
C35 C29 B2 C37 4.63(15) . . . . ?
C35 C36 C37 C45 -177.47(13) . . . . ?
C35 C36 C37 B2 2.94(16) . . . . ?
C35 C36 C48 C47 177.50(14) . . . . ?
C36 C37 C45 C46 -0.2(2) . . . . ?
C36 C37 B2 N2 -123.61(12) . . . . ?
C36 C37 B2 C28 127.07(13) . . . . ?
C36 C37 B2 C29 -4.49(15) . . . . ?
C37 C36 C48 C47 -0.2(2) . . . . ?
C37 C45 C46 C47 -0.6(2) . . . . ?
C38 C25 C26 C27 1.10(19) . . . . ?
C38 C39 C40 N2 178.53(12) . . . . ?
C38 C39 C40 C41 -1.5(2) . . . . ?
C39 C28 B2 N2 -3.93(12) . . . . ?
C39 C28 B2 C29 -126.30(14) . . . . ?
C39 C28 B2 C37 113.27(14) . . . . ?
C39 C40 C41 C42 -179.48(13) . . . . ?
C40 N2 C44 C43 0.68(19) . . . . ?
C40 N2 B2 C28 3.82(12) . . . . ?
C40 N2 B2 C29 132.20(11) . . . . ?
C40 N2 B2 C37 -116.90(12) . . . . ?
C40 C41 C42 C43 0.4(2) . . . . ?
C41 C42 C43 C44 -0.7(2) . . . . ?
C42 C43 C44 N2 0.2(2) . . . . ?
C44 N2 C40 C39 178.96(11) . . . . ?
C44 N2 C40 C41 -1.01(18) . . . . ?
C44 N2 B2 C28 -177.64(11) . . . . ?
C44 N2 B2 C29 -49.26(16) . . . . ?
C44 N2 B2 C37 61.63(17) . . . . ?
C45 C37 B2 N2 56.9(2) . . . . ?
C45 C37 B2 C28 -52.4(2) . . . . ?
C45 C37 B2 C29 176.00(15) . . . . ?
C45 C46 C47 C48 1.0(2) . . . . ?
C46 C47 C48 C36 -0.6(2) . . . . ?
C48 C36 C37 C45 0.6(2) . . . . ?
C48 C36 C37 B2 -178.99(13) . . . . ?
B1 N1 C5 C6 179.39(12) . . . . ?
B1 N1 C5 C9 -0.52(16) . . . . ?
B1 N1 C15 C14 -179.51(14) . . . . ?
B1 C4 C22 C21 1.72(15) . . . . ?
B1 C4 C22 C23 -177.49(12) . . . . ?
B1 C8 C9 C5 2.05(16) . . . . ?
B1 C8 C9 C10 -177.70(13) . . . . ?
B1 C8 C13 C12 177.09(15) . . . . ?
B1 C16 C17 C18 179.35(14) . . . . ?
B1 C16 C21 C20 -178.29(12) . . . . ?
B1 C16 C21 C22 2.23(15) . . . . ?
B2 N2 C40 C39 -2.41(14) . . . . ?
B2 N2 C40 C41 177.62(12) . . . . ?
B2 N2 C44 C43 -177.75(13) . . . . ?
B2 C28 C39 C38 -175.99(11) . . . . ?
B2 C28 C39 C40 3.04(14) . . . . ?
B2 C29 C30 C31 -179.93(14) . . . . ?
B2 C29 C35 C34 179.05(13) . . . . ?
B2 C29 C35 C36 -3.34(16) . . . . ?
B2 C37 C45 C46 179.28(15) . . . . ?

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

data_220623_ysg_hashizume_01_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2203033'
loop_
_audit_author_name
_audit_author_address
'Yusuke Yoshigoe'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-08-23 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-08-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C6.639 H5.161 B0.268 N0.268 O0.268, 1.728(C25 H20 B N O), 0.12(O1)'
_chemical_formula_sum            'C49.85 H39.53 B2 N2 O2.03'
_chemical_formula_weight         720.65
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.1041(15)
_cell_length_b                   8.6562(9)
_cell_length_c                   36.508(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.703(4)
_cell_angle_gamma                90
_cell_volume                     3820.8(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5735
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.831
_cell_measurement_theta_min      2.234
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.998
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1167 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.8854.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1515
_exptl_crystal_preparation       diffusion
_exptl_crystal_recrystallization_method diffusion
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            40071
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         1.977
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_special_details          none
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5249
_reflns_number_total             6976
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0042(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     925
_refine_ls_number_reflns         6976
_refine_ls_number_restraints     474
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0723
_refine_ls_restrained_S_all      1.040
_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)+(0.0515P)²+5.1634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1812
_refine_ls_wR_factor_ref         0.1943
_refine_special_details          none
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-O2
 1.377 with sigma of 0.02
 C75-C2
 1.508 with sigma of 0.02
 C25-C24
 1.508 with sigma of 0.02
 C78-C77
 1.474 with sigma of 0.01
 C56-C47
 1.474 with sigma of 0.01
3. Rigid bond restraints
 C75, C2
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 O2, C1, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C75) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C2, C75
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C75, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C70, C62, N15, C98, B14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 B15, N54, C81, C41, C43
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O2, C3, C1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N6, C3, C4, C8, C5, C7
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C27, C22, C28, C23, C26, C24
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C16, C21, C17, C20, C18, C19
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C9, C14, C10, C13, C11, C12
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N36, C37, C40, C39, C38, C35
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C30, C33, C29, C31, C34, C32
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C69, C70, C71, C73, C72, C74
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C64, C68, C67, C65, C66, N15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C25, C24
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C62, C57, C61, C58, C60, C59
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C2, C99, C6, C98, C88, C15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1, O2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(C5)=Sof(H5)=Sof(C4)=Sof(H4)=Sof(C3)=Sof(C8)=Sof(H8)=Sof(C7)=Sof(N6)=
 Sof(C14)=Sof(C9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=
 Sof(C13)=Sof(H13)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C22)=Sof(C27)=
 Sof(C28)=Sof(H28)=Sof(C26)=Sof(H26)=Sof(C24)=Sof(C23)=Sof(H23)=Sof(C21)=
 Sof(C20)=Sof(H20)=Sof(C19)=Sof(H19)=Sof(C18)=Sof(H18)=Sof(C17)=Sof(H17)=
 Sof(C16)=1-FVAR(1)
 Sof(O55)=Sof(N54)=Sof(C92)=Sof(C93)=Sof(C86)=Sof(H86)=Sof(C84)=Sof(H84)=
 Sof(C83)=Sof(H83)=Sof(C85)=Sof(H85)=Sof(C100)=Sof(H10A)=Sof(H10B)=Sof(H10C)=
 Sof(C81)=Sof(C41)=Sof(C79)=Sof(H79)=Sof(C43)=Sof(C36)=Sof(C82)=Sof(C78)=
 Sof(C94)=Sof(H94)=Sof(C77)=Sof(H77A)=Sof(H77B)=Sof(H77C)=Sof(C95)=Sof(C87)=
 Sof(H87)=Sof(C97)=Sof(H97)=Sof(C63)=Sof(H63)=Sof(C91)=Sof(H91)=Sof(C80)=
 Sof(H80)=Sof(C89)=Sof(H89)=Sof(C96)=Sof(H96)=Sof(C90)=Sof(H90)=FVAR(1)
 Sof(C69)=Sof(C70)=Sof(C71)=Sof(H71)=Sof(C72)=Sof(H72)=Sof(C73)=Sof(H73)=
 Sof(C74)=Sof(H74)=Sof(C60)=Sof(H60)=Sof(C61)=Sof(H61)=Sof(C62)=Sof(C57)=
 Sof(C58)=Sof(H58)=Sof(C59)=Sof(H59)=Sof(C76)=Sof(H76A)=Sof(H76B)=Sof(H76C)=
 Sof(O27)=Sof(N15)=Sof(C68)=Sof(C67)=Sof(H67)=Sof(C66)=Sof(C65)=Sof(H65)=
 Sof(C64)=Sof(H64)=Sof(C98)=Sof(C88)=Sof(H88)=Sof(C15)=Sof(H15)=Sof(C2)=
 Sof(C99)=Sof(H99)=Sof(C6)=Sof(B14)=1-FVAR(2)
 Sof(O41)=Sof(N36)=Sof(C30)=Sof(C37)=Sof(H37)=Sof(C53)=Sof(H53)=Sof(C54)=
 Sof(H54)=Sof(C47)=Sof(C44)=Sof(C49)=Sof(B43)=Sof(C50)=Sof(C40)=Sof(H40)=
 Sof(C51)=Sof(C39)=Sof(C33)=Sof(H33)=Sof(C38)=Sof(H38)=Sof(C29)=Sof(H29)=
 Sof(C46)=Sof(H46)=Sof(C31)=Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(H56C)=Sof(C42)=
 Sof(H42A)=Sof(H42B)=Sof(H42C)=Sof(C35)=Sof(C45)=Sof(H45)=Sof(C52)=Sof(H52)=
 Sof(C55)=Sof(H55)=Sof(C48)=Sof(H48)=Sof(C34)=Sof(H34)=Sof(C32)=Sof(H32)=FVAR(2)
 Fixed Sof: C75(0.2) H75A(0.2) H75B(0.2) H75C(0.2) O2(0.18) C1(0.18) H1A(0.18)
 H1B(0.18) H1C(0.18)
7.a Aromatic/amide H refined with riding coordinates:
 C71(H71), C72(H72), C73(H73), C74(H74), C37(H37), C53(H53), C54(H54),
 C60(H60), C61(H61), C58(H58), C59(H59), C67(H67), C65(H65), C64(H64), C88(H88),
  C15(H15), C99(H99), C40(H40), C33(H33), C38(H38), C29(H29), C46(H46),
 C45(H45), C52(H52), C55(H55), C48(H48), C34(H34), C32(H32), C86(H86), C84(H84),
  C83(H83), C85(H85), C79(H79), C5(H5), C4(H4), C8(H8), C94(H94), C10(H10),
 C11(H11), C12(H12), C13(H13), C87(H87), C97(H97), C63(H63), C28(H28), C26(H26),
  C23(H23), C91(H91), C20(H20), C19(H19), C18(H18), C17(H17), C80(H80),
 C89(H89), C96(H96), C90(H90)
7.b Fitted hexagon refined as free rotating group:
 C69(C70,C71,C72,C73,C74), C60(C61,C62,C57,C58,C59), N15(C68,C67,C66,C65,C64),
 C98(C88,C15,C2,C99,C6), C5(C4,C3,C8,C7,N6), C14(C9,C10,C11,C12,C13), C22(C27,
 C28,C26,C24,C23), C21(C20,C19,C18,C17,C16)
7.c Idealised Me refined as rotating group:
 C76(H76A,H76B,H76C), C75(H75A,H75B,H75C), C56(H56A,H56B,H56C), C42(H42A,H42B,
 H42C), C100(H10A,H10B,H10C), C1(H1A,H1B,H1C), C77(H77A,H77B,H77C), C25(H25A,
 H25B,H25C)
;
_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
C69 C 0.2860(18) 0.679(2) 0.3250(7) 0.030(4) Uani 0.268(5) 1 d G . P A 2
C70 C 0.347(2) 0.681(2) 0.3583(7) 0.038(5) Uani 0.268(5) 1 d G . P A 2
C71 C 0.4059(18) 0.552(2) 0.3699(5) 0.058(7) Uani 0.268(5) 1 d G . P A 2
H71 H 0.446471 0.552997 0.392191 0.070 Uiso 0.268(5) 1 calc R U P A 2
C72 C 0.4045(14) 0.4194(19) 0.3483(4) 0.044(5) Uani 0.268(5) 1 d G . P A 2
H72 H 0.444211 0.332418 0.356066 0.053 Uiso 0.268(5) 1 calc R U P A 2
C73 C 0.3439(15) 0.4171(18) 0.3150(4) 0.039(4) Uani 0.268(5) 1 d G . P A 2
H73 H 0.343008 0.328718 0.300500 0.047 Uiso 0.268(5) 1 calc R U P A 2
C74 C 0.2846(15) 0.547(2) 0.3033(5) 0.038(4) Uani 0.268(5) 1 d G . P A 2
H74 H 0.244063 0.545598 0.281058 0.045 Uiso 0.268(5) 1 calc R U P A 2
O41 O 0.1107(2) 0.9171(4) 0.50579(7) 0.0408(9) Uani 0.732(5) 1 d . . P A 1
N36 N 0.2743(4) 0.8624(7) 0.41090(12) 0.0245(10) Uani 0.732(5) 1 d . . P A 1
C30 C 0.4469(7) 0.9583(14) 0.3898(3) 0.0267(16) Uani 0.732(5) 1 d . . P A 1
C37 C 0.1786(4) 0.7894(6) 0.41641(14) 0.0276(10) Uani 0.732(5) 1 d . . P A 1
H37 H 0.148538 0.725337 0.398079 0.033 Uiso 0.732(5) 1 calc R U P A 1
C53 C 0.4215(5) 0.4129(7) 0.36081(16) 0.0312(12) Uani 0.732(5) 1 d . . P A 1
H53 H 0.456204 0.329612 0.372619 0.037 Uiso 0.732(5) 1 calc R U P A 1
C54 C 0.3732(5) 0.3946(7) 0.32597(17) 0.0300(13) Uani 0.732(5) 1 d . . P A 1
H54 H 0.378701 0.300106 0.314083 0.036 Uiso 0.732(5) 1 calc R U P A 1
C47 C 0.1389(4) 0.9652(6) 0.27440(11) 0.0275(10) Uani 0.732(5) 1 d D . P A 1
C60 C 0.6150(15) 1.083(3) 0.3819(4) 0.041(4) Uani 0.268(5) 1 d G . P A 2
H60 H 0.676377 1.101474 0.368145 0.050 Uiso 0.268(5) 1 calc R U P A 2
C61 C 0.5301(19) 0.989(3) 0.3679(5) 0.037(5) Uani 0.268(5) 1 d G . P A 2
H61 H 0.534706 0.944026 0.344874 0.044 Uiso 0.268(5) 1 calc R U P A 2
C62 C 0.4383(19) 0.961(4) 0.3885(8) 0.036(5) Uani 0.268(5) 1 d G . P A 2
C57 C 0.431(2) 1.027(4) 0.4229(7) 0.036(5) Uani 0.268(5) 1 d G . P A 2
C58 C 0.516(2) 1.122(3) 0.4369(5) 0.048(5) Uani 0.268(5) 1 d G . P A 2
H58 H 0.511596 1.166308 0.459913 0.058 Uiso 0.268(5) 1 calc R U P A 2
C59 C 0.6080(17) 1.150(3) 0.4163(4) 0.047(5) Uani 0.268(5) 1 d G . P A 2
H59 H 0.664821 1.212617 0.425666 0.057 Uiso 0.268(5) 1 calc R U P A 2
C76 C 0.030(2) 0.988(4) 0.2288(7) 0.080(8) Uani 0.268(5) 1 d . . P A 2
H76A H -0.015691 1.044488 0.211307 0.120 Uiso 0.268(5) 1 calc R U P A 2
H76B H -0.008942 0.899972 0.237196 0.120 Uiso 0.268(5) 1 calc R U P A 2
H76C H 0.096299 0.955104 0.217435 0.120 Uiso 0.268(5) 1 calc R U P A 2
C44 C 0.2682(7) 0.9212(10) 0.3402(2) 0.0256(13) Uani 0.732(5) 1 d . . P A 1
C49 C 0.2546(7) 0.8013(8) 0.3141(2) 0.0251(12) Uani 0.732(5) 1 d . . P A 1
B43 B 0.3443(10) 0.8545(15) 0.3744(2) 0.0232(16) Uani 0.732(5) 1 d . . P A 1
O27 O 0.0599(8) 1.0866(13) 0.2593(3) 0.057(3) Uani 0.268(5) 1 d . . P A 2
N15 N 0.2589(17) 0.917(2) 0.3456(4) 0.033(4) Uani 0.268(5) 1 d G . P A 2
C68 C 0.2305(17) 0.8168(16) 0.3169(5) 0.029(4) Uani 0.268(5) 1 d G . P A 2
C67 C 0.1650(13) 0.8689(14) 0.2871(4) 0.035(3) Uani 0.268(5) 1 d G . P A 2
H67 H 0.145967 0.801984 0.267909 0.042 Uiso 0.268(5) 1 calc R U P A 2
C66 C 0.1280(10) 1.0209(15) 0.2860(3) 0.033(3) Uani 0.268(5) 1 d G . P A 2
C65 C 0.1564(12) 1.1208(12) 0.3148(4) 0.039(4) Uani 0.268(5) 1 d G . P A 2
H65 H 0.131648 1.222553 0.314038 0.047 Uiso 0.268(5) 1 calc R U P A 2
C64 C 0.2219(15) 1.0688(19) 0.3445(3) 0.041(5) Uani 0.268(5) 1 d G . P A 2
H64 H 0.240919 1.135697 0.363754 0.050 Uiso 0.268(5) 1 calc R U P A 2
C98 C 0.2758(16) 0.861(3) 0.4178(4) 0.041(4) Uani 0.268(5) 1 d G . P A 2
C88 C 0.1752(14) 0.8052(19) 0.4290(3) 0.049(4) Uani 0.268(5) 1 d G . P A 2
H88 H 0.133202 0.739163 0.413894 0.058 Uiso 0.268(5) 1 calc R U P A 2
C15 C 0.1374(10) 0.8481(17) 0.4629(4) 0.052(5) Uani 0.268(5) 1 d G . P A 2
H15 H 0.070078 0.810709 0.470470 0.063 Uiso 0.268(5) 1 calc R U P A 2
C2 C 0.2001(13) 0.9468(19) 0.4856(3) 0.059(4) Uani 0.268(5) 1 d DG U P A 2
C99 C 0.3007(14) 1.003(2) 0.4743(5) 0.073(7) Uani 0.268(5) 1 d G . P A 2
H99 H 0.342719 1.068781 0.489493 0.087 Uiso 0.268(5) 1 calc R U P A 2
C6 C 0.3385(14) 0.960(3) 0.4404(5) 0.053(6) Uani 0.268(5) 1 d G U P A 2
B14 B 0.332(4) 0.852(5) 0.3801(10) 0.035(3) Uani 0.268(5) 1 d . . P A 2
C50 C 0.3117(7) 0.6572(8) 0.3266(2) 0.0226(13) Uani 0.732(5) 1 d . . P A 1
C75 C 0.163(3) 0.998(4) 0.5232(6) 0.074(9) Uani 0.2 1 d D U P A 2
H75A H 0.122206 1.092636 0.520716 0.111 Uiso 0.2 1 calc R U P A 2
H75B H 0.226287 1.012533 0.539521 0.111 Uiso 0.2 1 calc R U P A 2
H75C H 0.116107 0.919313 0.532908 0.111 Uiso 0.2 1 calc R U P A 2
C40 C 0.2685(5) 0.9820(7) 0.47039(14) 0.0353(11) Uani 0.732(5) 1 d . . P A 1
H40 H 0.298893 1.048278 0.488211 0.042 Uiso 0.732(5) 1 calc R U P A 1
C51 C 0.3636(7) 0.6799(8) 0.3617(2) 0.0243(14) Uani 0.732(5) 1 d . . P A 1
C39 C 0.1691(4) 0.9038(6) 0.47542(14) 0.0327(11) Uani 0.732(5) 1 d . . P A 1
C33 C 0.5961(5) 1.1545(9) 0.42926(17) 0.0376(14) Uani 0.732(5) 1 d . . P A 1
H33 H 0.645243 1.221054 0.441640 0.045 Uiso 0.732(5) 1 calc R U P A 1
C38 C 0.1242(4) 0.8062(5) 0.44806(14) 0.0311(10) Uani 0.732(5) 1 d . . P A 1
H38 H 0.058440 0.753585 0.451384 0.037 Uiso 0.732(5) 1 calc R U P A 1
C29 C 0.5463(6) 1.0021(11) 0.3754(2) 0.0271(12) Uani 0.732(5) 1 d . . P A 1
H29 H 0.563342 0.967619 0.352184 0.033 Uiso 0.732(5) 1 calc R U P A 1
C46 C 0.1535(4) 1.0824(6) 0.30023(14) 0.0283(12) Uani 0.732(5) 1 d . . P A 1
H46 H 0.120552 1.177977 0.295706 0.034 Uiso 0.732(5) 1 calc R U P A 1
C31 C 0.4264(7) 1.0137(14) 0.4255(3) 0.033(2) Uani 0.732(5) 1 d . . P A 1
C56 C 0.0670(5) 0.9927(8) 0.24045(16) 0.0376(14) Uani 0.732(5) 1 d D . P A 1
H56A H 0.101441 0.948801 0.219698 0.056 Uiso 0.732(5) 1 calc R U P A 1
H56B H 0.057356 1.101747 0.236775 0.056 Uiso 0.732(5) 1 calc R U P A 1
H56C H -0.003774 0.945039 0.243131 0.056 Uiso 0.732(5) 1 calc R U P A 1
C42 C 0.1462(6) 1.0319(8) 0.53222(14) 0.0474(15) Uani 0.732(5) 1 d . . P A 1
H42A H 0.146411 1.131499 0.520666 0.071 Uiso 0.732(5) 1 calc R U P A 1
H42B H 0.219466 1.007651 0.541713 0.071 Uiso 0.732(5) 1 calc R U P A 1
H42C H 0.096447 1.033201 0.551930 0.071 Uiso 0.732(5) 1 calc R U P A 1
C35 C 0.3199(5) 0.9566(9) 0.43767(17) 0.0284(12) Uani 0.732(5) 1 d . . P A 1
C45 C 0.2168(5) 1.0597(7) 0.33295(15) 0.0274(11) Uani 0.732(5) 1 d . . P A 1
H45 H 0.224047 1.139487 0.349950 0.033 Uiso 0.732(5) 1 calc R U P A 1
C52 C 0.4184(5) 0.5548(8) 0.37809(19) 0.0279(11) Uani 0.732(5) 1 d . . P A 1
H52 H 0.453533 0.566815 0.401118 0.034 Uiso 0.732(5) 1 calc R U P A 1
C55 C 0.3166(5) 0.5152(8) 0.30852(17) 0.0257(12) Uani 0.732(5) 1 d . . P A 1
H55 H 0.282743 0.501846 0.285341 0.031 Uiso 0.732(5) 1 calc R U P A 1
C48 C 0.1902(4) 0.8231(6) 0.28176(14) 0.0262(10) Uani 0.732(5) 1 d . . P A 1
H48 H 0.181530 0.742683 0.264987 0.031 Uiso 0.732(5) 1 calc R U P A 1
C34 C 0.6208(5) 1.0968(9) 0.39498(17) 0.0318(13) Uani 0.732(5) 1 d . . P A 1
H34 H 0.687909 1.121922 0.385070 0.038 Uiso 0.732(5) 1 calc R U P A 1
C32 C 0.4987(6) 1.1128(11) 0.4449(2) 0.0393(15) Uani 0.732(5) 1 d . . P A 1
H32 H 0.481663 1.150052 0.467850 0.047 Uiso 0.732(5) 1 calc R U P A 1
B15 B 0.8343(3) 0.6487(4) 0.37763(8) 0.0301(7) Uani 1 1 d . . . . .
O55 O 0.5599(2) 0.4099(3) 0.26032(7) 0.0228(7) Uani 0.734(6) 1 d . . P B 2
O2 O 0.6116(14) 0.583(2) 0.5050(4) 0.070(4) Uani 0.18 1 d D U P B 1
N54 N 0.7550(6) 0.5735(8) 0.34667(16) 0.0240(11) Uani 0.734(6) 1 d . . P B 2
C92 C 0.7865(8) 0.8196(9) 0.3256(2) 0.0227(16) Uani 0.734(6) 1 d . . P B 2
C93 C 0.7290(6) 0.6700(7) 0.31838(18) 0.0200(12) Uani 0.734(6) 1 d . . P B 2
C86 C 1.1142(5) 0.4124(7) 0.37853(15) 0.0306(12) Uani 0.734(6) 1 d . . P B 2
H86 H 1.174627 0.392305 0.364435 0.037 Uiso 0.734(6) 1 calc R U P B 2
C84 C 1.0209(6) 0.3781(9) 0.43471(18) 0.0331(13) Uani 0.734(6) 1 d . . P B 2
H84 H 1.016842 0.333607 0.457793 0.040 Uiso 0.734(6) 1 calc R U P B 2
C83 C 0.8046(5) 0.4909(10) 0.4746(2) 0.0370(14) Uani 0.734(6) 1 d . . P B 2
H83 H 0.849000 0.425534 0.489133 0.044 Uiso 0.734(6) 1 calc R U P B 2
C85 C 1.1084(4) 0.3456(6) 0.41317(16) 0.0307(12) Uani 0.734(6) 1 d . . P B 2
H85 H 1.163923 0.278786 0.421770 0.037 Uiso 0.734(6) 1 calc R U P B 2
C100 C 0.5319(4) 0.5049(6) 0.22863(11) 0.0286(10) Uani 0.734(6) 1 d . . P B 2
H10A H 0.489550 0.445220 0.210811 0.043 Uiso 0.734(6) 1 calc R U P B 2
H10B H 0.598469 0.540598 0.218111 0.043 Uiso 0.734(6) 1 calc R U P B 2
H10C H 0.489052 0.592023 0.235949 0.043 Uiso 0.734(6) 1 calc R U P B 2
C81 C 0.7733(8) 0.6348(14) 0.4170(3) 0.0270(17) Uani 0.734(6) 1 d . . P B 2
C1 C 0.635(3) 0.468(4) 0.5312(9) 0.070(7) Uani 0.18 1 d D U P B 1
H1A H 0.712033 0.470834 0.538578 0.105 Uiso 0.18 1 calc R U P B 1
H1B H 0.616817 0.368570 0.520914 0.105 Uiso 0.18 1 calc R U P B 1
H1C H 0.591609 0.485528 0.552225 0.105 Uiso 0.18 1 calc R U P B 1
C41 C 0.9408(6) 0.5439(11) 0.3859(2) 0.0257(13) Uani 0.734(6) 1 d . . P B 2
C79 C 0.6416(4) 0.6462(6) 0.46500(14) 0.0307(12) Uani 0.734(6) 1 d . . P B 2
H79 H 0.575603 0.685141 0.473262 0.037 Uiso 0.734(6) 1 calc R U P B 2
C43 C 0.8500(10) 0.8148(11) 0.3590(3) 0.027(2) Uani 0.734(6) 1 d . . P B 2
C36 C 0.9387(6) 0.4784(12) 0.4215(2) 0.0272(15) Uani 0.734(6) 1 d . . P B 2
C82 C 0.8372(7) 0.5339(13) 0.4400(2) 0.0294(18) Uani 0.734(6) 1 d . . P B 2
C78 C 0.7045(5) 0.5462(8) 0.48743(13) 0.0365(12) Uani 0.734(6) 1 d D . P B 2
C5 C 0.6795(18) 0.705(3) 0.4183(4) 0.044(5) Uani 0.266(6) 1 d G . P B 1
H5 H 0.648702 0.770789 0.400483 0.053 Uiso 0.266(6) 1 calc R U P B 1
C4 C 0.6274(12) 0.6830(18) 0.4510(5) 0.054(4) Uani 0.266(6) 1 d G . P B 1
H4 H 0.561728 0.734594 0.455114 0.065 Uiso 0.266(6) 1 calc R U P B 1
C3 C 0.6734(15) 0.584(2) 0.4776(4) 0.051(4) Uani 0.266(6) 1 d G U P B 1
C8 C 0.7716(16) 0.507(2) 0.4714(5) 0.051(5) Uani 0.266(6) 1 d G . P B 1
H8 H 0.802401 0.441136 0.489217 0.061 Uiso 0.266(6) 1 calc R U P B 1
C7 C 0.8237(17) 0.529(3) 0.4387(7) 0.042(6) Uani 0.266(6) 1 d G . P B 1
N6 N 0.778(2) 0.628(4) 0.4121(5) 0.043(7) Uani 0.266(6) 1 d G . P B 1
C94 C 0.6627(4) 0.6230(6) 0.28827(13) 0.0207(10) Uani 0.734(6) 1 d . . P B 2
H94 H 0.644822 0.690745 0.269128 0.025 Uiso 0.734(6) 1 calc R U P B 2
C14 C 0.9427(18) 0.535(3) 0.3909(6) 0.036(5) Uani 0.266(6) 1 d G U P B 1
C9 C 0.9213(16) 0.478(4) 0.4255(7) 0.036(5) Uani 0.266(6) 1 d G U P B 1
C10 C 0.9975(17) 0.382(3) 0.4438(5) 0.048(5) Uani 0.266(6) 1 d G . P B 1
H10 H 0.983261 0.343845 0.466921 0.058 Uiso 0.266(6) 1 calc R U P B 1
C11 C 1.0951(15) 0.342(2) 0.4275(4) 0.060(6) Uani 0.266(6) 1 d G . P B 1
H11 H 1.146096 0.277902 0.439706 0.071 Uiso 0.266(6) 1 calc R U P B 1
C12 C 1.1164(14) 0.399(2) 0.3929(4) 0.046(5) Uani 0.266(6) 1 d G . P B 1
H12 H 1.181718 0.372605 0.381996 0.055 Uiso 0.266(6) 1 calc R U P B 1
C13 C 1.0402(19) 0.495(3) 0.3746(4) 0.037(4) Uani 0.266(6) 1 d G . P B 1
H13 H 1.054507 0.533252 0.351502 0.044 Uiso 0.266(6) 1 calc R U P B 1
C77 C 0.6629(5) 0.4950(9) 0.52333(16) 0.0573(18) Uani 0.734(6) 1 d D . P B 2
H77A H 0.594235 0.546033 0.527502 0.086 Uiso 0.734(6) 1 calc R U P B 2
H77B H 0.716255 0.520905 0.542654 0.086 Uiso 0.734(6) 1 calc R U P B 2
H77C H 0.651593 0.385274 0.522904 0.086 Uiso 0.734(6) 1 calc R U P B 2
C95 C 0.6237(3) 0.4709(5) 0.28763(11) 0.0187(9) Uani 0.734(6) 1 d . . P B 2
C25 C 0.5619(17) 0.492(4) 0.2414(6) 0.084(8) Uani 0.266(6) 1 d D . P B 1
H25A H 0.536139 0.387631 0.241740 0.126 Uiso 0.266(6) 1 calc R U P B 1
H25B H 0.603636 0.508897 0.220046 0.126 Uiso 0.266(6) 1 calc R U P B 1
H25C H 0.499745 0.561451 0.240890 0.126 Uiso 0.266(6) 1 calc R U P B 1
C87 C 1.0300(6) 0.5090(10) 0.36502(18) 0.0283(12) Uani 0.734(6) 1 d . . P B 2
H87 H 1.033752 0.550829 0.341645 0.034 Uiso 0.734(6) 1 calc R U P B 2
C97 C 0.7169(5) 0.4278(7) 0.34566(15) 0.0271(10) Uani 0.734(6) 1 d . . P B 2
H97 H 0.735478 0.362152 0.365154 0.033 Uiso 0.734(6) 1 calc R U P B 2
C63 C 0.9115(8) 0.9460(10) 0.3686(2) 0.0277(13) Uani 0.734(6) 1 d . . P B 2
H63 H 0.955761 0.946403 0.390081 0.033 Uiso 0.734(6) 1 calc R U P B 2
C22 C 0.7469(19) 0.6971(19) 0.3142(5) 0.035(5) Uani 0.266(6) 1 d G . P B 1
C27 C 0.761(2) 0.582(2) 0.3405(4) 0.032(5) Uani 0.266(6) 1 d G . P B 1
C28 C 0.7132(17) 0.438(2) 0.3346(4) 0.055(6) Uani 0.266(6) 1 d G . P B 1
H28 H 0.722855 0.360581 0.352254 0.066 Uiso 0.266(6) 1 calc R U P B 1
C26 C 0.6506(13) 0.4086(14) 0.3025(4) 0.051(5) Uani 0.266(6) 1 d G . P B 1
H26 H 0.618446 0.312111 0.298557 0.061 Uiso 0.266(6) 1 calc R U P B 1
C24 C 0.6362(12) 0.5238(17) 0.2762(3) 0.046(4) Uani 0.266(6) 1 d DG . P B 1
C23 C 0.6844(15) 0.6680(16) 0.2820(4) 0.045(4) Uani 0.266(6) 1 d G . P B 1
H23 H 0.674703 0.745108 0.264400 0.055 Uiso 0.266(6) 1 calc R U P B 1
C91 C 0.7824(6) 0.9485(8) 0.30279(19) 0.0279(13) Uani 0.734(6) 1 d . . P B 2
H91 H 0.739886 0.947884 0.280894 0.033 Uiso 0.734(6) 1 calc R U P B 2
C21 C 0.799(3) 0.837(3) 0.3251(8) 0.048(8) Uani 0.266(6) 1 d G . P B 1
C20 C 0.810(2) 0.977(3) 0.3067(6) 0.051(6) Uani 0.266(6) 1 d G . P B 1
H20 H 0.777130 0.989186 0.283304 0.061 Uiso 0.266(6) 1 calc R U P B 1
C19 C 0.869(2) 1.097(2) 0.3233(6) 0.051(6) Uani 0.266(6) 1 d G . P B 1
H19 H 0.875875 1.190772 0.311008 0.061 Uiso 0.266(6) 1 calc R U P B 1
C18 C 0.918(2) 1.079(3) 0.3583(5) 0.050(6) Uani 0.266(6) 1 d G . P B 1
H18 H 0.957135 1.159507 0.369367 0.061 Uiso 0.266(6) 1 calc R U P B 1
C17 C 0.907(3) 0.939(3) 0.3766(6) 0.052(7) Uani 0.266(6) 1 d G . P B 1
H17 H 0.939652 0.926656 0.400024 0.062 Uiso 0.266(6) 1 calc R U P B 1
C16 C 0.848(3) 0.818(3) 0.3600(8) 0.040(8) Uani 0.266(6) 1 d G . P B 1
C80 C 0.6753(6) 0.6894(8) 0.43039(16) 0.0274(12) Uani 0.734(6) 1 d . . P B 2
H80 H 0.631204 0.755947 0.416052 0.033 Uiso 0.734(6) 1 calc R U P B 2
C89 C 0.9076(7) 1.0763(9) 0.34624(19) 0.0307(14) Uani 0.734(6) 1 d . . P B 2
H89 H 0.948227 1.163655 0.353138 0.037 Uiso 0.734(6) 1 calc R U P B 2
C96 C 0.6522(4) 0.3730(5) 0.31718(11) 0.0247(9) Uani 0.734(6) 1 d . . P B 2
H96 H 0.626950 0.271542 0.317265 0.030 Uiso 0.734(6) 1 calc R U P B 2
C90 C 0.8426(6) 1.0767(8) 0.31340(18) 0.0298(14) Uani 0.734(6) 1 d . . P B 2
H90 H 0.840293 1.164460 0.298686 0.036 Uiso 0.734(6) 1 calc R U P B 2
O101 O 1.1896(17) 0.248(2) 0.4286(6) 0.062(9) Uani 0.120(8) 1 d . . . C 3


_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
C69 C70 1.3900 . ?
C69 C74 1.3900 . ?
C69 C68 1.392(16) . ?
C70 C71 1.3900 . ?
C70 B14 1.69(5) . ?
C71 H71 0.9300 . ?
C71 C72 1.3900 . ?
C72 H72 0.9300 . ?
C72 C73 1.3900 . ?
C73 H73 0.9300 . ?
C73 C74 1.3900 . ?
C74 H74 0.9300 . ?
O41 C39 1.347(5) . ?
O41 C42 1.437(7) . ?
N36 C37 1.343(5) . ?
N36 B43 1.615(7) . ?
N36 C35 1.369(5) . ?
C30 B43 1.613(14) . ?
C30 C29 1.389(6) . ?
C30 C31 1.420(5) . ?
C37 H37 0.9300 . ?
C37 C38 1.365(6) . ?
C53 H53 0.9300 . ?
C53 C54 1.384(7) . ?
C53 C52 1.382(6) . ?
C54 H54 0.9300 . ?
C54 C55 1.386(6) . ?
C47 C46 1.390(6) . ?
C47 C56 1.499(6) . ?
C47 C48 1.399(6) . ?
C60 H60 0.9300 . ?
C60 C61 1.3900 . ?
C60 C59 1.3900 . ?
C61 H61 0.9300 . ?
C61 C62 1.3900 . ?
C62 C57 1.3900 . ?
C62 B14 1.62(5) . ?
C57 C58 1.3900 . ?
C57 C6 1.44(2) . ?
C58 H58 0.9300 . ?
C58 C59 1.3900 . ?
C59 H59 0.9300 . ?
C76 H76A 0.9600 . ?
C76 H76B 0.9600 . ?
C76 H76C 0.9600 . ?
C76 O27 1.43(2) . ?
C44 C49 1.411(6) . ?
C44 B43 1.623(13) . ?
C44 C45 1.370(6) . ?
C49 C50 1.487(8) . ?
C49 C48 1.398(6) . ?
B43 C51 1.602(13) . ?
O27 C66 1.370(13) . ?
N15 C68 1.3900 . ?
N15 C64 1.3900 . ?
N15 B14 1.60(5) . ?
C68 C67 1.3900 . ?
C67 H67 0.9300 . ?
C67 C66 1.3900 . ?
C66 C65 1.3900 . ?
C65 H65 0.9300 . ?
C65 C64 1.3900 . ?
C64 H64 0.9300 . ?
C98 C88 1.3900 . ?
C98 C6 1.3900 . ?
C98 B14 1.56(3) . ?
C88 H88 0.9300 . ?
C88 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C2 1.3900 . ?
C2 C99 1.3900 . ?
C2 C75 1.530(17) . ?
C99 H99 0.9300 . ?
C99 C6 1.3900 . ?
C50 C51 1.413(5) . ?
C50 C55 1.398(5) . ?
C75 H75A 0.9600 . ?
C75 H75B 0.9600 . ?
C75 H75C 0.9600 . ?
C40 H40 0.9300 . ?
C40 C39 1.400(7) . ?
C40 C35 1.390(5) . ?
C51 C52 1.390(6) . ?
C39 C38 1.399(7) . ?
C33 H33 0.9300 . ?
C33 C34 1.393(7) . ?
C33 C32 1.382(7) . ?
C38 H38 0.9300 . ?
C29 H29 0.9300 . ?
C29 C34 1.392(6) . ?
C46 H46 0.9300 . ?
C46 C45 1.403(6) . ?
C31 C35 1.469(9) . ?
C31 C32 1.394(6) . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C45 H45 0.9300 . ?
C52 H52 0.9300 . ?
C55 H55 0.9300 . ?
C48 H48 0.9300 . ?
C34 H34 0.9300 . ?
C32 H32 0.9300 . ?
B15 N54 1.587(5) . ?
B15 C81 1.652(7) . ?
B15 C41 1.593(7) . ?
B15 C43 1.605(8) . ?
B15 N6 1.473(12) . ?
B15 C14 1.694(15) . ?
B15 C27 1.685(11) . ?
B15 C16 1.61(2) . ?
O55 C100 1.447(5) . ?
O55 C95 1.340(4) . ?
O2 C1 1.401(18) . ?
O2 C3 1.278(19) . ?
N54 C93 1.354(5) . ?
N54 C97 1.343(5) . ?
C92 C93 1.488(9) . ?
C92 C43 1.412(5) . ?
C92 C91 1.392(5) . ?
C93 C94 1.391(5) . ?
C86 H86 0.9300 . ?
C86 C85 1.395(6) . ?
C86 C87 1.391(6) . ?
C84 H84 0.9300 . ?
C84 C85 1.378(6) . ?
C84 C36 1.390(6) . ?
C83 H83 0.9300 . ?
C83 C82 1.390(6) . ?
C83 C78 1.404(7) . ?
C85 H85 0.9300 . ?
C100 H10A 0.9600 . ?
C100 H10B 0.9600 . ?
C100 H10C 0.9600 . ?
C81 C82 1.416(6) . ?
C81 C80 1.387(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C41 C36 1.419(5) . ?
C41 C87 1.384(5) . ?
C79 H79 0.9300 . ?
C79 C78 1.393(6) . ?
C79 C80 1.397(6) . ?
C43 C63 1.393(5) . ?
C36 C82 1.509(8) . ?
C78 C77 1.493(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.3900 . ?
C5 N6 1.3900 . ?
C4 H4 0.9300 . ?
C4 C3 1.3900 . ?
C3 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C7 1.3900 . ?
C7 N6 1.3900 . ?
C7 C9 1.369(19) . ?
C94 H94 0.9300 . ?
C94 C95 1.398(5) . ?
C14 C9 1.3900 . ?
C14 C13 1.3900 . ?
C9 C10 1.3900 . ?
C10 H10 0.9300 . ?
C10 C11 1.3900 . ?
C11 H11 0.9300 . ?
C11 C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C13 1.3900 . ?
C13 H13 0.9300 . ?
C77 H77A 0.9600 . ?
C77 H77B 0.9600 . ?
C77 H77C 0.9600 . ?
C95 C96 1.402(6) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C25 C24 1.544(15) . ?
C87 H87 0.9300 . ?
C97 H97 0.9300 . ?
C97 C96 1.358(6) . ?
C63 H63 0.9300 . ?
C63 C89 1.391(6) . ?
C22 C27 1.3900 . ?
C22 C23 1.3900 . ?
C22 C21 1.42(2) . ?
C27 C28 1.3900 . ?
C28 H28 0.9300 . ?
C28 C26 1.3900 . ?
C26 H26 0.9300 . ?
C26 C24 1.3900 . ?
C24 C23 1.3900 . ?
C23 H23 0.9300 . ?
C91 H91 0.9300 . ?
C91 C90 1.373(7) . ?
C21 C20 1.3900 . ?
C21 C16 1.3900 . ?
C20 H20 0.9300 . ?
C20 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C16 1.3900 . ?
C80 H80 0.9300 . ?
C89 H89 0.9300 . ?
C89 C90 1.403(7) . ?
C96 H96 0.9300 . ?
C90 H90 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
C70 C69 C74 120.0 . . ?
C70 C69 C68 113.8(16) . . ?
C74 C69 C68 126.2(16) . . ?
C69 C70 B14 111(2) . . ?
C71 C70 C69 120.0 . . ?
C71 C70 B14 129(2) . . ?
C70 C71 H71 120.0 . . ?
C70 C71 C72 120.0 . . ?
C72 C71 H71 120.0 . . ?
C71 C72 H72 120.0 . . ?
C73 C72 C71 120.0 . . ?
C73 C72 H72 120.0 . . ?
C72 C73 H73 120.0 . . ?
C74 C73 C72 120.0 . . ?
C74 C73 H73 120.0 . . ?
C69 C74 H74 120.0 . . ?
C73 C74 C69 120.0 . . ?
C73 C74 H74 120.0 . . ?
C39 O41 C42 117.3(4) . . ?
C37 N36 B43 126.4(6) . . ?
C37 N36 C35 119.7(4) . . ?
C35 N36 B43 113.9(6) . . ?
C29 C30 B43 133.3(6) . . ?
C29 C30 C31 116.6(4) . . ?
C31 C30 B43 110.1(6) . . ?
N36 C37 H37 119.0 . . ?
N36 C37 C38 122.1(4) . . ?
C38 C37 H37 119.0 . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
C52 C53 C54 120.1(4) . . ?
C53 C54 H54 119.5 . . ?
C53 C54 C55 121.0(4) . . ?
C55 C54 H54 119.5 . . ?
C46 C47 C56 119.7(5) . . ?
C46 C47 C48 118.0(4) . . ?
C48 C47 C56 122.2(5) . . ?
C61 C60 H60 120.0 . . ?
C61 C60 C59 120.0 . . ?
C59 C60 H60 120.0 . . ?
C60 C61 H61 120.0 . . ?
C60 C61 C62 120.0 . . ?
C62 C61 H61 120.0 . . ?
C61 C62 B14 130.6(19) . . ?
C57 C62 C61 120.0 . . ?
C57 C62 B14 109.3(19) . . ?
C62 C57 C58 120.0 . . ?
C62 C57 C6 108.4(18) . . ?
C58 C57 C6 130.8(19) . . ?
C57 C58 H58 120.0 . . ?
C57 C58 C59 120.0 . . ?
C59 C58 H58 120.0 . . ?
C60 C59 H59 120.0 . . ?
C58 C59 C60 120.0 . . ?
C58 C59 H59 120.0 . . ?
H76A C76 H76B 109.5 . . ?
H76A C76 H76C 109.5 . . ?
H76B C76 H76C 109.5 . . ?
O27 C76 H76A 109.5 . . ?
O27 C76 H76B 109.5 . . ?
O27 C76 H76C 109.5 . . ?
C49 C44 B43 107.4(7) . . ?
C45 C44 C49 118.5(4) . . ?
C45 C44 B43 134.0(7) . . ?
C44 C49 C50 111.9(6) . . ?
C48 C49 C44 120.8(4) . . ?
C48 C49 C50 127.2(6) . . ?
N36 B43 C44 108.6(7) . . ?
C30 B43 N36 96.5(7) . . ?
C30 B43 C44 118.1(9) . . ?
C51 B43 N36 111.6(7) . . ?
C51 B43 C30 120.4(9) . . ?
C51 B43 C44 101.5(7) . . ?
C66 O27 C76 115.3(14) . . ?
C68 N15 C64 120.0 . . ?
C68 N15 B14 118.7(19) . . ?
C64 N15 B14 121.2(19) . . ?
N15 C68 C69 105.8(15) . . ?
C67 C68 C69 134.0(15) . . ?
C67 C68 N15 120.0 . . ?
C68 C67 H67 120.0 . . ?
C68 C67 C66 120.0 . . ?
C66 C67 H67 120.0 . . ?
O27 C66 C67 126.5(10) . . ?
O27 C66 C65 113.4(10) . . ?
C67 C66 C65 120.0 . . ?
C66 C65 H65 120.0 . . ?
C64 C65 C66 120.0 . . ?
C64 C65 H65 120.0 . . ?
N15 C64 H64 120.0 . . ?
C65 C64 N15 120.0 . . ?
C65 C64 H64 120.0 . . ?
C88 C98 C6 120.0 . . ?
C88 C98 B14 132(2) . . ?
C6 C98 B14 108(2) . . ?
C98 C88 H88 120.0 . . ?
C15 C88 C98 120.0 . . ?
C15 C88 H88 120.0 . . ?
C88 C15 H15 120.0 . . ?
C88 C15 C2 120.0 . . ?
C2 C15 H15 120.0 . . ?
C15 C2 C99 120.0 . . ?
C15 C2 C75 122.2(19) . . ?
C99 C2 C75 117.8(19) . . ?
C2 C99 H99 120.0 . . ?
C2 C99 C6 120.0 . . ?
C6 C99 H99 120.0 . . ?
C98 C6 C57 113.6(17) . . ?
C99 C6 C57 125.6(17) . . ?
C99 C6 C98 120.0 . . ?
C62 B14 C70 120(3) . . ?
N15 B14 C70 90(2) . . ?
N15 B14 C62 110(3) . . ?
C98 B14 C70 121(3) . . ?
C98 B14 C62 100(3) . . ?
C98 B14 N15 115(3) . . ?
C51 C50 C49 110.0(6) . . ?
C55 C50 C49 128.5(6) . . ?
C55 C50 C51 121.5(4) . . ?
C2 C75 H75A 109.5 . . ?
C2 C75 H75B 109.5 . . ?
C2 C75 H75C 109.5 . . ?
H75A C75 H75B 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?
C39 C40 H40 121.4 . . ?
C35 C40 H40 121.4 . . ?
C35 C40 C39 117.3(4) . . ?
C50 C51 B43 109.2(7) . . ?
C52 C51 B43 133.1(7) . . ?
C52 C51 C50 117.7(4) . . ?
O41 C39 C40 123.7(5) . . ?
O41 C39 C38 116.0(5) . . ?
C38 C39 C40 120.4(4) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C32 C33 C34 120.1(4) . . ?
C37 C38 C39 118.8(4) . . ?
C37 C38 H38 120.6 . . ?
C39 C38 H38 120.6 . . ?
C30 C29 H29 119.4 . . ?
C30 C29 C34 121.2(4) . . ?
C34 C29 H29 119.4 . . ?
C47 C46 H46 119.2 . . ?
C47 C46 C45 121.5(4) . . ?
C45 C46 H46 119.2 . . ?
C30 C31 C35 111.0(6) . . ?
C32 C31 C30 122.8(4) . . ?
C32 C31 C35 126.3(7) . . ?
C47 C56 H56A 109.5 . . ?
C47 C56 H56B 109.5 . . ?
C47 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
O41 C42 H42A 109.5 . . ?
O41 C42 H42B 109.5 . . ?
O41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N36 C35 C40 121.7(4) . . ?
N36 C35 C31 108.3(6) . . ?
C40 C35 C31 129.9(6) . . ?
C44 C45 C46 120.7(4) . . ?
C44 C45 H45 119.6 . . ?
C46 C45 H45 119.6 . . ?
C53 C52 C51 121.2(4) . . ?
C53 C52 H52 119.4 . . ?
C51 C52 H52 119.4 . . ?
C54 C55 C50 118.4(4) . . ?
C54 C55 H55 120.8 . . ?
C50 C55 H55 120.8 . . ?
C47 C48 H48 119.8 . . ?
C49 C48 C47 120.4(4) . . ?
C49 C48 H48 119.8 . . ?
C33 C34 H34 119.6 . . ?
C29 C34 C33 120.8(4) . . ?
C29 C34 H34 119.6 . . ?
C33 C32 C31 118.5(5) . . ?
C33 C32 H32 120.7 . . ?
C31 C32 H32 120.7 . . ?
N54 B15 C81 108.1(6) . . ?
N54 B15 C41 110.9(5) . . ?
N54 B15 C43 98.4(4) . . ?
C41 B15 C81 100.7(5) . . ?
C41 B15 C43 118.6(6) . . ?
C43 B15 C81 120.0(6) . . ?
N6 B15 C14 93.9(12) . . ?
N6 B15 C27 113.4(15) . . ?
N6 B15 C16 120.9(17) . . ?
C27 B15 C14 113.6(14) . . ?
C16 B15 C14 123.5(17) . . ?
C16 B15 C27 93.0(13) . . ?
C95 O55 C100 118.4(3) . . ?
C3 O2 C1 116(2) . . ?
C93 N54 B15 113.7(5) . . ?
C97 N54 B15 126.9(4) . . ?
C97 N54 C93 119.4(4) . . ?
C43 C92 C93 111.0(6) . . ?
C91 C92 C93 126.1(6) . . ?
C91 C92 C43 122.9(4) . . ?
N54 C93 C92 108.2(6) . . ?
N54 C93 C94 121.8(4) . . ?
C94 C93 C92 129.9(6) . . ?
C85 C86 H86 119.9 . . ?
C87 C86 H86 119.9 . . ?
C87 C86 C85 120.2(4) . . ?
C85 C84 H84 120.5 . . ?
C85 C84 C36 119.1(4) . . ?
C36 C84 H84 120.5 . . ?
C82 C83 H83 120.0 . . ?
C82 C83 C78 119.9(4) . . ?
C78 C83 H83 120.0 . . ?
C86 C85 H85 119.8 . . ?
C84 C85 C86 120.4(4) . . ?
C84 C85 H85 119.8 . . ?
O55 C100 H10A 109.5 . . ?
O55 C100 H10B 109.5 . . ?
O55 C100 H10C 109.5 . . ?
H10A C100 H10B 109.5 . . ?
H10A C100 H10C 109.5 . . ?
H10B C100 H10C 109.5 . . ?
C82 C81 B15 107.9(6) . . ?
C80 C81 B15 135.0(7) . . ?
C80 C81 C82 117.0(5) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C36 C41 B15 110.6(5) . . ?
C87 C41 B15 131.8(5) . . ?
C87 C41 C36 117.7(4) . . ?
C78 C79 H79 119.2 . . ?
C78 C79 C80 121.5(4) . . ?
C80 C79 H79 119.2 . . ?
C92 C43 B15 108.8(6) . . ?
C63 C43 B15 134.2(6) . . ?
C63 C43 C92 117.0(4) . . ?
C84 C36 C41 121.7(4) . . ?
C84 C36 C82 128.8(6) . . ?
C41 C36 C82 109.5(6) . . ?
C83 C82 C81 122.2(4) . . ?
C83 C82 C36 126.4(6) . . ?
C81 C82 C36 111.4(6) . . ?
C83 C78 C77 121.6(5) . . ?
C79 C78 C83 118.1(4) . . ?
C79 C78 C77 120.2(5) . . ?
C4 C5 H5 120.0 . . ?
C4 C5 N6 120.0 . . ?
N6 C5 H5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C3 C4 H4 120.0 . . ?
O2 C3 C4 108.8(15) . . ?
O2 C3 C8 131.2(15) . . ?
C4 C3 C8 120.0 . . ?
C3 C8 H8 120.0 . . ?
C7 C8 C3 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C7 N6 120.0 . . ?
C9 C7 C8 133.9(19) . . ?
C9 C7 N6 106.0(19) . . ?
C5 N6 B15 121.0(15) . . ?
C7 N6 B15 119.0(15) . . ?
C7 N6 C5 120.0 . . ?
C93 C94 H94 121.0 . . ?
C93 C94 C95 118.0(3) . . ?
C95 C94 H94 121.0 . . ?
C9 C14 B15 107.0(13) . . ?
C9 C14 C13 120.0 . . ?
C13 C14 B15 133.0(13) . . ?
C7 C9 C14 114.0(18) . . ?
C7 C9 C10 126.0(18) . . ?
C10 C9 C14 120.0 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C78 C77 H77A 109.5 . . ?
C78 C77 H77B 109.5 . . ?
C78 C77 H77C 109.5 . . ?
H77A C77 H77B 109.5 . . ?
H77A C77 H77C 109.5 . . ?
H77B C77 H77C 109.5 . . ?
O55 C95 C94 124.4(4) . . ?
O55 C95 C96 116.5(4) . . ?
C94 C95 C96 119.1(3) . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
C86 C87 H87 119.5 . . ?
C41 C87 C86 121.0(4) . . ?
C41 C87 H87 119.5 . . ?
N54 C97 H97 118.9 . . ?
N54 C97 C96 122.3(4) . . ?
C96 C97 H97 118.9 . . ?
C43 C63 H63 119.6 . . ?
C89 C63 C43 120.8(4) . . ?
C89 C63 H63 119.6 . . ?
C27 C22 C23 120.0 . . ?
C27 C22 C21 112.4(18) . . ?
C23 C22 C21 127.6(18) . . ?
C22 C27 B15 110.7(11) . . ?
C28 C27 B15 129.2(11) . . ?
C28 C27 C22 120.0 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C26 120.0 . . ?
C26 C28 H28 120.0 . . ?
C28 C26 H26 120.0 . . ?
C24 C26 C28 120.0 . . ?
C24 C26 H26 120.0 . . ?
C26 C24 C25 119.4(15) . . ?
C26 C24 C23 120.0 . . ?
C23 C24 C25 120.5(15) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C92 C91 H91 120.8 . . ?
C90 C91 C92 118.4(4) . . ?
C90 C91 H91 120.8 . . ?
C20 C21 C22 131(2) . . ?
C20 C21 C16 120.0 . . ?
C16 C21 C22 109(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C21 C16 B15 115.1(18) . . ?
C17 C16 B15 124.8(18) . . ?
C17 C16 C21 120.0 . . ?
C81 C80 C79 121.2(4) . . ?
C81 C80 H80 119.4 . . ?
C79 C80 H80 119.4 . . ?
C63 C89 H89 119.8 . . ?
C63 C89 C90 120.3(4) . . ?
C90 C89 H89 119.8 . . ?
C95 C96 H96 120.3 . . ?
C97 C96 C95 119.4(4) . . ?
C97 C96 H96 120.3 . . ?
C91 C90 C89 120.5(4) . . ?
C91 C90 H90 119.7 . . ?
C89 C90 H90 119.7 . . ?

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
C69 C70 C71 C72 0.0 . . . . ?
C69 C70 B14 C62 -118(3) . . . . ?
C69 C70 B14 N15 -4(2) . . . . ?
C69 C70 B14 C98 116(3) . . . . ?
C69 C68 C67 C66 -175(2) . . . . ?
C70 C69 C74 C73 0.0 . . . . ?
C70 C69 C68 N15 2.2(14) . . . . ?
C70 C69 C68 C67 177.3(15) . . . . ?
C70 C71 C72 C73 0.0 . . . . ?
C71 C70 B14 C62 64(4) . . . . ?
C71 C70 B14 N15 178.1(17) . . . . ?
C71 C70 B14 C98 -62(4) . . . . ?
C71 C72 C73 C74 0.0 . . . . ?
C72 C73 C74 C69 0.0 . . . . ?
C74 C69 C70 C71 0.0 . . . . ?
C74 C69 C70 B14 -178(2) . . . . ?
C74 C69 C68 N15 -178.1(14) . . . . ?
C74 C69 C68 C67 -3(3) . . . . ?
O41 C39 C38 C37 179.2(4) . . . . ?
N36 C37 C38 C39 0.7(6) . . . . ?
N36 B43 C51 C50 117.5(7) . . . . ?
N36 B43 C51 C52 -62.2(12) . . . . ?
C30 B43 C51 C50 -130.6(8) . . . . ?
C30 B43 C51 C52 49.7(12) . . . . ?
C30 C29 C34 C33 -2.1(7) . . . . ?
C30 C31 C35 N36 1.8(8) . . . . ?
C30 C31 C35 C40 179.8(7) . . . . ?
C30 C31 C32 C33 -2.3(8) . . . . ?
C37 N36 B43 C30 -176.3(7) . . . . ?
C37 N36 B43 C44 61.1(10) . . . . ?
C37 N36 B43 C51 -49.9(11) . . . . ?
C37 N36 C35 C40 -1.5(7) . . . . ?
C37 N36 C35 C31 176.7(8) . . . . ?
C53 C54 C55 C50 1.5(6) . . . . ?
C54 C53 C52 C51 2.4(6) . . . . ?
C47 C46 C45 C44 1.2(7) . . . . ?
C60 C61 C62 C57 0.0 . . . . ?
C60 C61 C62 B14 -177(3) . . . . ?
C61 C60 C59 C58 0.0 . . . . ?
C61 C62 C57 C58 0.0 . . . . ?
C61 C62 C57 C6 -170(3) . . . . ?
C61 C62 B14 C70 36(5) . . . . ?
C61 C62 B14 N15 -66(4) . . . . ?
C61 C62 B14 C98 172(2) . . . . ?
C62 C57 C58 C59 0.0 . . . . ?
C62 C57 C6 C98 -6.0(19) . . . . ?
C62 C57 C6 C99 -176.0(13) . . . . ?
C57 C62 B14 C70 -141(2) . . . . ?
C57 C62 B14 N15 117(2) . . . . ?
C57 C62 B14 C98 -6(3) . . . . ?
C57 C58 C59 C60 0.0 . . . . ?
C58 C57 C6 C98 -175.1(17) . . . . ?
C58 C57 C6 C99 15(4) . . . . ?
C59 C60 C61 C62 0.0 . . . . ?
C76 O27 C66 C67 -3.8(19) . . . . ?
C76 O27 C66 C65 178.7(15) . . . . ?
C44 C49 C50 C51 0.7(8) . . . . ?
C44 C49 C50 C55 179.8(7) . . . . ?
C44 C49 C48 C47 0.6(8) . . . . ?
C44 B43 C51 C50 2.0(7) . . . . ?
C44 B43 C51 C52 -177.7(8) . . . . ?
C49 C44 B43 N36 -119.3(7) . . . . ?
C49 C44 B43 C30 132.4(7) . . . . ?
C49 C44 B43 C51 -1.6(8) . . . . ?
C49 C44 C45 C46 -0.9(8) . . . . ?
C49 C50 C51 B43 -1.7(7) . . . . ?
C49 C50 C51 C52 178.1(8) . . . . ?
C49 C50 C55 C54 -178.5(9) . . . . ?
B43 N36 C37 C38 -178.5(7) . . . . ?
B43 N36 C35 C40 177.4(7) . . . . ?
B43 N36 C35 C31 -4.4(9) . . . . ?
B43 C30 C29 C34 178.9(12) . . . . ?
B43 C30 C31 C35 1.5(9) . . . . ?
B43 C30 C31 C32 -176.8(10) . . . . ?
B43 C44 C49 C50 0.7(8) . . . . ?
B43 C44 C49 C48 178.6(7) . . . . ?
B43 C44 C45 C46 -179.0(9) . . . . ?
B43 C51 C52 C53 179.4(9) . . . . ?
O27 C66 C65 C64 177.7(12) . . . . ?
N15 C68 C67 C66 0.0 . . . . ?
C68 C69 C70 C71 180(2) . . . . ?
C68 C69 C70 B14 2(2) . . . . ?
C68 C69 C74 C73 -180(2) . . . . ?
C68 N15 C64 C65 0.0 . . . . ?
C68 N15 B14 C70 6(2) . . . . ?
C68 N15 B14 C62 128(2) . . . . ?
C68 N15 B14 C98 -119(3) . . . . ?
C68 C67 C66 O27 -177.3(14) . . . . ?
C68 C67 C66 C65 0.0 . . . . ?
C67 C66 C65 C64 0.0 . . . . ?
C66 C65 C64 N15 0.0 . . . . ?
C64 N15 C68 C69 175.9(19) . . . . ?
C64 N15 C68 C67 0.0 . . . . ?
C64 N15 B14 C70 -175.8(15) . . . . ?
C64 N15 B14 C62 -54(3) . . . . ?
C64 N15 B14 C98 59(4) . . . . ?
C98 C88 C15 C2 0.0 . . . . ?
C88 C98 C6 C57 -171(3) . . . . ?
C88 C98 C6 C99 0.0 . . . . ?
C88 C98 B14 C70 -52(5) . . . . ?
C88 C98 B14 C62 174(2) . . . . ?
C88 C98 B14 N15 55(4) . . . . ?
C88 C15 C2 C99 0.0 . . . . ?
C88 C15 C2 C75 -180(2) . . . . ?
C15 C2 C99 C6 0.0 . . . . ?
C2 C99 C6 C57 169(3) . . . . ?
C2 C99 C6 C98 0.0 . . . . ?
C6 C57 C58 C59 168(3) . . . . ?
C6 C98 C88 C15 0.0 . . . . ?
C6 C98 B14 C70 136(3) . . . . ?
C6 C98 B14 C62 2(3) . . . . ?
C6 C98 B14 N15 -116(3) . . . . ?
B14 C70 C71 C72 178(3) . . . . ?
B14 C62 C57 C58 178(3) . . . . ?
B14 C62 C57 C6 7(2) . . . . ?
B14 N15 C68 C69 -6(2) . . . . ?
B14 N15 C68 C67 178(2) . . . . ?
B14 N15 C64 C65 -178(2) . . . . ?
B14 C98 C88 C15 -171(3) . . . . ?
B14 C98 C6 C57 2(3) . . . . ?
B14 C98 C6 C99 173(2) . . . . ?
C50 C49 C48 C47 178.1(8) . . . . ?
C50 C51 C52 C53 -0.4(6) . . . . ?
C75 C2 C99 C6 180(2) . . . . ?
C40 C39 C38 C37 -0.4(6) . . . . ?
C51 C50 C55 C54 0.6(7) . . . . ?
C39 C40 C35 N36 1.7(7) . . . . ?
C39 C40 C35 C31 -176.0(10) . . . . ?
C29 C30 B43 N36 177.0(9) . . . . ?
C29 C30 B43 C44 -67.9(13) . . . . ?
C29 C30 B43 C51 57.3(14) . . . . ?
C29 C30 C31 C35 -179.0(9) . . . . ?
C29 C30 C31 C32 2.8(8) . . . . ?
C46 C47 C48 C49 -0.3(6) . . . . ?
C31 C30 B43 N36 -3.5(9) . . . . ?
C31 C30 B43 C44 111.6(7) . . . . ?
C31 C30 B43 C51 -123.2(7) . . . . ?
C31 C30 C29 C34 -0.6(7) . . . . ?
C56 C47 C46 C45 177.7(5) . . . . ?
C56 C47 C48 C49 -178.5(6) . . . . ?
C42 O41 C39 C40 7.8(6) . . . . ?
C42 O41 C39 C38 -171.8(4) . . . . ?
C35 N36 C37 C38 0.3(6) . . . . ?
C35 N36 B43 C30 4.8(9) . . . . ?
C35 N36 B43 C44 -117.8(7) . . . . ?
C35 N36 B43 C51 131.2(7) . . . . ?
C35 C40 C39 O41 179.7(5) . . . . ?
C35 C40 C39 C38 -0.8(6) . . . . ?
C35 C31 C32 C33 179.7(11) . . . . ?
C45 C44 C49 C50 -177.8(8) . . . . ?
C45 C44 C49 C48 0.0(8) . . . . ?
C45 C44 B43 N36 59.0(12) . . . . ?
C45 C44 B43 C30 -49.4(12) . . . . ?
C45 C44 B43 C51 176.6(9) . . . . ?
C52 C53 C54 C55 -3.0(6) . . . . ?
C55 C50 C51 B43 179.1(8) . . . . ?
C55 C50 C51 C52 -1.1(6) . . . . ?
C48 C47 C46 C45 -0.6(6) . . . . ?
C48 C49 C50 C51 -177.0(7) . . . . ?
C48 C49 C50 C55 2.1(14) . . . . ?
C34 C33 C32 C31 -0.5(7) . . . . ?
C32 C33 C34 C29 2.6(7) . . . . ?
C32 C31 C35 N36 180.0(7) . . . . ?
C32 C31 C35 C40 -2.0(16) . . . . ?
B15 N54 C93 C92 0.8(7) . . . . ?
B15 N54 C93 C94 178.4(7) . . . . ?
B15 N54 C97 C96 -177.7(6) . . . . ?
B15 C81 C82 C83 -176.3(9) . . . . ?
B15 C81 C82 C36 1.6(8) . . . . ?
B15 C81 C80 C79 174.6(11) . . . . ?
B15 C41 C36 C84 177.9(8) . . . . ?
B15 C41 C36 C82 -1.5(8) . . . . ?
B15 C41 C87 C86 -179.9(9) . . . . ?
B15 C43 C63 C89 -179.7(11) . . . . ?
B15 C14 C9 C7 -1(2) . . . . ?
B15 C14 C9 C10 -179(2) . . . . ?
B15 C14 C13 C12 179(3) . . . . ?
B15 C27 C28 C26 176(2) . . . . ?
O55 C95 C96 C97 179.8(4) . . . . ?
O2 C3 C8 C7 -180(2) . . . . ?
N54 B15 C81 C82 114.1(6) . . . . ?
N54 B15 C81 C80 -61.0(12) . . . . ?
N54 B15 C41 C36 -111.9(5) . . . . ?
N54 B15 C41 C87 68.3(8) . . . . ?
N54 B15 C43 C92 1.6(7) . . . . ?
N54 B15 C43 C63 -177.3(9) . . . . ?
N54 C93 C94 C95 -0.6(7) . . . . ?
N54 C97 C96 C95 0.0(6) . . . . ?
C92 C93 C94 C95 176.4(8) . . . . ?
C92 C43 C63 C89 1.5(7) . . . . ?
C92 C91 C90 C89 0.8(6) . . . . ?
C93 N54 C97 C96 -0.3(7) . . . . ?
C93 C92 C43 B15 -1.3(8) . . . . ?
C93 C92 C43 C63 177.7(8) . . . . ?
C93 C92 C91 C90 -178.7(8) . . . . ?
C93 C94 C95 O55 -179.5(5) . . . . ?
C93 C94 C95 C96 0.4(6) . . . . ?
C84 C36 C82 C83 -1.7(16) . . . . ?
C84 C36 C82 C81 -179.5(8) . . . . ?
C85 C86 C87 C41 1.7(7) . . . . ?
C85 C84 C36 C41 2.2(7) . . . . ?
C85 C84 C36 C82 -178.6(11) . . . . ?
C100 O55 C95 C94 2.2(5) . . . . ?
C100 O55 C95 C96 -177.7(3) . . . . ?
C81 B15 N54 C93 124.0(6) . . . . ?
C81 B15 N54 C97 -58.4(8) . . . . ?
C81 B15 C41 C36 2.2(7) . . . . ?
C81 B15 C41 C87 -177.5(8) . . . . ?
C81 B15 C43 C92 -115.0(7) . . . . ?
C81 B15 C43 C63 66.2(12) . . . . ?
C1 O2 C3 C4 169(2) . . . . ?
C1 O2 C3 C8 -12(3) . . . . ?
C41 B15 N54 C93 -126.5(5) . . . . ?
C41 B15 N54 C97 51.0(8) . . . . ?
C41 B15 C81 C82 -2.3(7) . . . . ?
C41 B15 C81 C80 -177.3(11) . . . . ?
C41 B15 C43 C92 121.0(6) . . . . ?
C41 B15 C43 C63 -57.8(12) . . . . ?
C41 C36 C82 C83 177.7(8) . . . . ?
C41 C36 C82 C81 -0.1(8) . . . . ?
C43 B15 N54 C93 -1.4(7) . . . . ?
C43 B15 N54 C97 176.1(7) . . . . ?
C43 B15 C81 C82 -134.5(6) . . . . ?
C43 B15 C81 C80 50.5(14) . . . . ?
C43 B15 C41 C36 135.3(6) . . . . ?
C43 B15 C41 C87 -44.4(10) . . . . ?
C43 C92 C93 N54 0.4(7) . . . . ?
C43 C92 C93 C94 -176.9(7) . . . . ?
C43 C92 C91 C90 -0.2(6) . . . . ?
C43 C63 C89 C90 -1.0(7) . . . . ?
C36 C84 C85 C86 -0.1(7) . . . . ?
C36 C41 C87 C86 0.4(6) . . . . ?
C82 C83 C78 C79 -1.2(9) . . . . ?
C82 C83 C78 C77 176.1(8) . . . . ?
C82 C81 C80 C79 0.0(8) . . . . ?
C78 C83 C82 C81 0.9(9) . . . . ?
C78 C83 C82 C36 -176.6(11) . . . . ?
C78 C79 C80 C81 -0.3(8) . . . . ?
C5 C4 C3 O2 180.0(17) . . . . ?
C5 C4 C3 C8 0.0 . . . . ?
C4 C5 N6 B15 180(3) . . . . ?
C4 C5 N6 C7 0.0 . . . . ?
C4 C3 C8 C7 0.0 . . . . ?
C3 C8 C7 N6 0.0 . . . . ?
C3 C8 C7 C9 176(4) . . . . ?
C8 C7 N6 B15 -180(3) . . . . ?
C8 C7 N6 C5 0.0 . . . . ?
C8 C7 C9 C14 -178(2) . . . . ?
C8 C7 C9 C10 1(5) . . . . ?
C7 C9 C10 C11 -178(3) . . . . ?
N6 B15 C14 C9 2.0(17) . . . . ?
N6 B15 C14 C13 -177(2) . . . . ?
N6 B15 C27 C22 124.9(13) . . . . ?
N6 B15 C27 C28 -52(2) . . . . ?
N6 B15 C16 C21 -119.9(18) . . . . ?
N6 B15 C16 C17 63(3) . . . . ?
N6 C5 C4 C3 0.0 . . . . ?
N6 C7 C9 C14 -1(2) . . . . ?
N6 C7 C9 C10 177.1(18) . . . . ?
C94 C95 C96 C97 -0.1(5) . . . . ?
C14 B15 N6 C5 176.9(19) . . . . ?
C14 B15 N6 C7 -3.1(18) . . . . ?
C14 B15 C27 C22 -129.5(12) . . . . ?
C14 B15 C27 C28 54(2) . . . . ?
C14 B15 C16 C21 120.8(18) . . . . ?
C14 B15 C16 C17 -56(2) . . . . ?
C14 C9 C10 C11 0.0 . . . . ?
C9 C7 N6 B15 3(2) . . . . ?
C9 C7 N6 C5 -177(3) . . . . ?
C9 C14 C13 C12 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C13 C14 C9 C7 179(3) . . . . ?
C13 C14 C9 C10 0.0 . . . . ?
C25 C24 C23 C22 177.0(16) . . . . ?
C87 C86 C85 C84 -1.8(7) . . . . ?
C87 C41 C36 C84 -2.3(6) . . . . ?
C87 C41 C36 C82 178.3(9) . . . . ?
C97 N54 C93 C92 -177.0(7) . . . . ?
C97 N54 C93 C94 0.6(7) . . . . ?
C63 C89 C90 C91 -0.2(7) . . . . ?
C22 C27 C28 C26 0.0 . . . . ?
C22 C21 C20 C19 -178(3) . . . . ?
C22 C21 C16 B15 1.1(19) . . . . ?
C22 C21 C16 C17 178(3) . . . . ?
C27 B15 N6 C5 -65(2) . . . . ?
C27 B15 N6 C7 114.7(15) . . . . ?
C27 B15 C14 C9 -115.7(12) . . . . ?
C27 B15 C14 C13 65(2) . . . . ?
C27 B15 C16 C21 -0.2(18) . . . . ?
C27 B15 C16 C17 -177.5(19) . . . . ?
C27 C22 C23 C24 0.0 . . . . ?
C27 C22 C21 C20 176.6(19) . . . . ?
C27 C22 C21 C16 -1.6(18) . . . . ?
C27 C28 C26 C24 0.0 . . . . ?
C28 C26 C24 C25 -177.0(16) . . . . ?
C28 C26 C24 C23 0.0 . . . . ?
C26 C24 C23 C22 0.0 . . . . ?
C23 C22 C27 B15 -177.0(18) . . . . ?
C23 C22 C27 C28 0.0 . . . . ?
C23 C22 C21 C20 -5(4) . . . . ?
C23 C22 C21 C16 176.7(17) . . . . ?
C91 C92 C93 N54 179.0(6) . . . . ?
C91 C92 C93 C94 1.7(13) . . . . ?
C91 C92 C43 B15 -180.0(8) . . . . ?
C91 C92 C43 C63 -0.9(7) . . . . ?
C21 C22 C27 B15 1.5(18) . . . . ?
C21 C22 C27 C28 179(2) . . . . ?
C21 C22 C23 C24 -178(3) . . . . ?
C21 C20 C19 C18 0.0 . . . . ?
C20 C21 C16 B15 -177(2) . . . . ?
C20 C21 C16 C17 0.0 . . . . ?
C20 C19 C18 C17 0.0 . . . . ?
C19 C18 C17 C16 0.0 . . . . ?
C18 C17 C16 B15 177(3) . . . . ?
C18 C17 C16 C21 0.0 . . . . ?
C16 B15 N6 C5 44(3) . . . . ?
C16 B15 N6 C7 -136.4(17) . . . . ?
C16 B15 C14 C9 133.4(17) . . . . ?
C16 B15 C14 C13 -45(3) . . . . ?
C16 B15 C27 C22 -0.7(16) . . . . ?
C16 B15 C27 C28 -177(2) . . . . ?
C16 C21 C20 C19 0.0 . . . . ?
C80 C81 C82 C83 -0.3(8) . . . . ?
C80 C81 C82 C36 177.6(11) . . . . ?
C80 C79 C78 C83 0.9(9) . . . . ?
C80 C79 C78 C77 -176.4(6) . . . . ?

_olex2_exptl_crystal_mounting_method cryoroop
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_211006_ysg_hashizume_01_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2203032'
loop_
_audit_author_name
_audit_author_address
'Yusuke Yoshigoe'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-08-23 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_audit_creation_date             2021-10-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H15 B F3 N'
_chemical_formula_sum            'C24 H15 B F3 N'
_chemical_formula_weight         385.18
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.1093(2)
_cell_length_b                   11.4141(3)
_cell_length_c                   17.6390(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1834.01(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      30.97
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.7072
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1081 before and 0.0664 after correction.
The Ratio of minimum to maximum transmission is 0.9477.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 1.00 0.00 0.1180
1.00 -1.00 0.00 0.1940
-1.00 0.00 1.00 0.0430
-1.00 -1.00 1.00 0.1140
1.00 0.00 -1.00 0.1840
0.00 -1.00 0.00 0.2380
0.00 1.00 0.00 0.1300
0.00 -1.00 -1.00 0.2360
0.00 0.00 -1.00 0.1390
-1.00 -1.00 -1.00 0.1610
1.00 0.00 1.00 0.0870
-1.00 0.00 -1.00 0.1330
-1.00 1.00 -1.00 0.1390
1.00 1.00 0.00 0.0770
1.00 -1.00 -1.00 0.2090
0.00 0.00 1.00 0.1080

_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.246
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            36578
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.435
_diffrn_reflns_theta_min         2.125
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.801
_reflns_number_gt                4630
_reflns_number_total             5201
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1729 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(2)
_refine_ls_extinction_coef       0.0067(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.042
_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)+(0.0367P)²+0.4887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0896
_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:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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 0.8137(2) 0.02536(10) 0.47871(8) 0.0464(4) Uani 1 1 d . . . . .
F2 F 0.62357(15) 0.12676(16) 0.50433(9) 0.0548(5) Uani 1 1 d . . . . .
F3 F 0.83580(18) 0.18553(11) 0.53897(7) 0.0431(4) Uani 1 1 d . . . . .
N1 N 0.45088(16) 0.46566(13) 0.30056(8) 0.0173(3) Uani 1 1 d . . . . .
C1 C 0.7625(2) 0.13547(16) 0.48184(12) 0.0248(4) Uani 1 1 d . . . . .
C2 C 0.7785(2) 0.20032(15) 0.40884(11) 0.0212(4) Uani 1 1 d . . . . .
C3 C 0.6945(2) 0.30139(15) 0.39649(10) 0.0195(3) Uani 1 1 d . . . . .
H3 H 0.630367 0.327610 0.433835 0.023 Uiso 1 1 calc R U . . .
C4 C 0.70659(19) 0.36234(14) 0.32899(10) 0.0172(3) Uani 1 1 d . . . . .
C5 C 0.3850(2) 0.55110(14) 0.34214(10) 0.0169(3) Uani 1 1 d . . . . .
C6 C 0.2346(2) 0.54983(16) 0.35370(10) 0.0205(4) Uani 1 1 d . . . . .
H6 H 0.189627 0.608126 0.382303 0.025 Uiso 1 1 calc R U . . .
C7 C 0.1523(2) 0.46054(17) 0.32204(11) 0.0236(4) Uani 1 1 d . . . . .
H7 H 0.051379 0.457691 0.329849 0.028 Uiso 1 1 calc R U . . .
C8 C 0.8766(2) 0.16057(15) 0.35417(12) 0.0232(4) Uani 1 1 d . . . . .
H8 H 0.933134 0.094169 0.363221 0.028 Uiso 1 1 calc R U . . .
C9 C 0.8898(2) 0.22049(15) 0.28609(11) 0.0211(4) Uani 1 1 d . . . . .
H9 H 0.954920 0.194201 0.249221 0.025 Uiso 1 1 calc R U . . .
C10 C 0.80505(19) 0.32029(14) 0.27307(10) 0.0175(3) Uani 1 1 d . . . . .
C11 C 0.6902(2) 0.48202(14) 0.21213(10) 0.0182(3) Uani 1 1 d . . . . .
C12 C 0.6580(2) 0.55224(15) 0.15008(11) 0.0223(4) Uani 1 1 d . . . . .
H12 H 0.589167 0.611998 0.154552 0.027 Uiso 1 1 calc R U . . .
C13 C 0.7291(2) 0.53328(17) 0.08073(11) 0.0255(4) Uani 1 1 d . . . . .
H13 H 0.704833 0.579070 0.038964 0.031 Uiso 1 1 calc R U . . .
C14 C 0.8353(2) 0.44693(16) 0.07375(11) 0.0245(4) Uani 1 1 d . . . . .
H14 H 0.883295 0.436456 0.027711 0.029 Uiso 1 1 calc R U . . .
C15 C 0.87039(19) 0.37596(16) 0.13512(10) 0.0206(3) Uani 1 1 d . . . . .
H15 H 0.942428 0.318623 0.130720 0.025 Uiso 1 1 calc R U . . .
C16 C 0.79576(19) 0.39206(14) 0.20360(10) 0.0179(3) Uani 1 1 d . . . . .
C17 C 0.3706(2) 0.38008(16) 0.26866(10) 0.0217(4) Uani 1 1 d . . . . .
H17 H 0.416986 0.323271 0.239428 0.026 Uiso 1 1 calc R U . . .
C18 C 0.2208(2) 0.37512(17) 0.27853(11) 0.0257(4) Uani 1 1 d . . . . .
H18 H 0.166286 0.315366 0.256371 0.031 Uiso 1 1 calc R U . . .
C19 C 0.49657(18) 0.63293(14) 0.37048(9) 0.0161(3) Uani 1 1 d . . . . .
C20 C 0.4720(2) 0.73421(15) 0.41313(10) 0.0192(3) Uani 1 1 d . . . . .
H20 H 0.377333 0.756976 0.426267 0.023 Uiso 1 1 calc R U . . .
C21 C 0.5927(2) 0.79985(16) 0.43532(11) 0.0213(4) Uani 1 1 d . . . . .
H21 H 0.579366 0.867983 0.463396 0.026 Uiso 1 1 calc R U . . .
C22 C 0.7340(2) 0.76409(15) 0.41570(11) 0.0211(4) Uani 1 1 d . . . . .
H22 H 0.814312 0.808362 0.431217 0.025 Uiso 1 1 calc R U . . .
C23 C 0.7565(2) 0.66272(14) 0.37307(11) 0.0195(4) Uani 1 1 d . . . . .
H23 H 0.851573 0.639602 0.360940 0.023 Uiso 1 1 calc R U . . .
C24 C 0.63753(19) 0.59570(14) 0.34849(10) 0.0167(3) Uani 1 1 d . . . . .
B1 B 0.6260(2) 0.47919(16) 0.29794(11) 0.0176(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 C1 1.342(2) . ?
F2 C1 1.330(2) . ?
F3 C1 1.337(2) . ?
N1 C5 1.360(2) . ?
N1 C17 1.344(2) . ?
N1 B1 1.603(2) . ?
C1 C2 1.492(3) . ?
C2 C3 1.401(3) . ?
C2 C8 1.391(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(2) . ?
C4 C10 1.417(2) . ?
C4 B1 1.618(3) . ?
C5 C6 1.385(2) . ?
C5 C19 1.468(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(3) . ?
C7 H7 0.9300 . ?
C7 C18 1.389(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.395(2) . ?
C10 C16 1.476(2) . ?
C11 C12 1.388(3) . ?
C11 C16 1.415(2) . ?
C11 B1 1.623(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.401(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.398(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.376(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.397(2) . ?
C19 C24 1.407(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.394(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.395(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.396(2) . ?
C24 B1 1.605(2) . ?

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
C5 N1 B1 112.69(14) . . ?
C17 N1 C5 120.45(16) . . ?
C17 N1 B1 126.83(15) . . ?
F1 C1 C2 113.27(17) . . ?
F2 C1 F1 105.86(17) . . ?
F2 C1 F3 106.41(18) . . ?
F2 C1 C2 112.80(16) . . ?
F3 C1 F1 104.92(16) . . ?
F3 C1 C2 112.91(16) . . ?
C3 C2 C1 119.28(18) . . ?
C8 C2 C1 119.95(17) . . ?
C8 C2 C3 120.77(17) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.29(17) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C10 118.63(16) . . ?
C3 C4 B1 132.05(16) . . ?
C10 C4 B1 109.32(15) . . ?
N1 C5 C6 120.57(16) . . ?
N1 C5 C19 109.52(15) . . ?
C6 C5 C19 129.89(16) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 118.97(17) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C18 119.78(17) . . ?
C18 C7 H7 120.1 . . ?
C2 C8 H8 120.2 . . ?
C9 C8 C2 119.66(16) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.82(17) . . ?
C10 C9 H9 120.1 . . ?
C4 C10 C16 110.71(15) . . ?
C9 C10 C4 120.81(17) . . ?
C9 C10 C16 128.42(16) . . ?
C12 C11 C16 118.60(16) . . ?
C12 C11 B1 132.14(16) . . ?
C16 C11 B1 109.24(15) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.12(17) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.66(18) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.38(17) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 118.99(17) . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C10 110.70(15) . . ?
C15 C16 C10 128.04(16) . . ?
C15 C16 C11 121.18(17) . . ?
N1 C17 H17 119.5 . . ?
N1 C17 C18 121.09(18) . . ?
C18 C17 H17 119.5 . . ?
C7 C18 H18 120.4 . . ?
C17 C18 C7 119.12(18) . . ?
C17 C18 H18 120.4 . . ?
C20 C19 C5 126.78(16) . . ?
C20 C19 C24 122.98(16) . . ?
C24 C19 C5 110.24(15) . . ?
C19 C20 H20 120.9 . . ?
C21 C20 C19 118.15(16) . . ?
C21 C20 H20 120.9 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.26(16) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.82(17) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.53(17) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 B1 110.10(15) . . ?
C23 C24 C19 117.23(15) . . ?
C23 C24 B1 132.67(16) . . ?
N1 B1 C4 111.25(14) . . ?
N1 B1 C11 112.78(15) . . ?
N1 B1 C24 97.42(13) . . ?
C4 B1 C11 99.71(13) . . ?
C24 B1 C4 117.73(15) . . ?
C24 B1 C11 118.56(14) . . ?

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
F1 C1 C2 C3 161.84(17) . . . . ?
F1 C1 C2 C8 -18.5(3) . . . . ?
F2 C1 C2 C3 41.6(2) . . . . ?
F2 C1 C2 C8 -138.7(2) . . . . ?
F3 C1 C2 C3 -79.1(2) . . . . ?
F3 C1 C2 C8 100.6(2) . . . . ?
N1 C5 C6 C7 -0.2(3) . . . . ?
N1 C5 C19 C20 177.67(16) . . . . ?
N1 C5 C19 C24 -2.2(2) . . . . ?
N1 C17 C18 C7 0.2(3) . . . . ?
C1 C2 C3 C4 -179.43(16) . . . . ?
C1 C2 C8 C9 179.26(17) . . . . ?
C2 C3 C4 C10 0.1(3) . . . . ?
C2 C3 C4 B1 179.67(17) . . . . ?
C2 C8 C9 C10 0.2(3) . . . . ?
C3 C2 C8 C9 -1.1(3) . . . . ?
C3 C4 C10 C9 -0.9(3) . . . . ?
C3 C4 C10 C16 176.38(15) . . . . ?
C3 C4 B1 N1 -55.2(2) . . . . ?
C3 C4 B1 C11 -174.40(18) . . . . ?
C3 C4 B1 C24 56.0(3) . . . . ?
C4 C10 C16 C11 -0.5(2) . . . . ?
C4 C10 C16 C15 -177.17(17) . . . . ?
C5 N1 C17 C18 -1.5(3) . . . . ?
C5 N1 B1 C4 123.06(15) . . . . ?
C5 N1 B1 C11 -125.87(15) . . . . ?
C5 N1 B1 C24 -0.58(18) . . . . ?
C5 C6 C7 C18 -0.9(3) . . . . ?
C5 C19 C20 C21 179.37(17) . . . . ?
C5 C19 C24 C23 -178.16(15) . . . . ?
C5 C19 C24 B1 1.81(19) . . . . ?
C6 C5 C19 C20 -4.1(3) . . . . ?
C6 C5 C19 C24 176.04(18) . . . . ?
C6 C7 C18 C17 1.0(3) . . . . ?
C8 C2 C3 C4 0.9(3) . . . . ?
C8 C9 C10 C4 0.8(3) . . . . ?
C8 C9 C10 C16 -176.02(17) . . . . ?
C9 C10 C16 C11 176.52(17) . . . . ?
C9 C10 C16 C15 -0.1(3) . . . . ?
C10 C4 B1 N1 124.43(15) . . . . ?
C10 C4 B1 C11 5.22(18) . . . . ?
C10 C4 B1 C24 -124.42(17) . . . . ?
C11 C12 C13 C14 -2.0(3) . . . . ?
C12 C11 C16 C10 -174.78(15) . . . . ?
C12 C11 C16 C15 2.1(3) . . . . ?
C12 C11 B1 N1 55.1(2) . . . . ?
C12 C11 B1 C4 173.15(18) . . . . ?
C12 C11 B1 C24 -57.8(3) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C10 173.70(17) . . . . ?
C14 C15 C16 C11 -2.6(3) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
C16 C11 B1 N1 -123.61(16) . . . . ?
C16 C11 B1 C4 -5.54(17) . . . . ?
C16 C11 B1 C24 123.55(17) . . . . ?
C17 N1 C5 C6 1.5(3) . . . . ?
C17 N1 C5 C19 179.90(15) . . . . ?
C17 N1 B1 C4 -55.0(2) . . . . ?
C17 N1 B1 C11 56.1(2) . . . . ?
C17 N1 B1 C24 -178.66(16) . . . . ?
C19 C5 C6 C7 -178.34(17) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C19 C24 B1 N1 -0.78(17) . . . . ?
C19 C24 B1 C4 -119.55(17) . . . . ?
C19 C24 B1 C11 120.25(17) . . . . ?
C20 C19 C24 C23 1.9(2) . . . . ?
C20 C19 C24 B1 -178.08(16) . . . . ?
C20 C21 C22 C23 0.5(3) . . . . ?
C21 C22 C23 C24 0.7(3) . . . . ?
C22 C23 C24 C19 -1.9(3) . . . . ?
C22 C23 C24 B1 178.15(18) . . . . ?
C23 C24 B1 N1 179.19(18) . . . . ?
C23 C24 B1 C4 60.4(3) . . . . ?
C23 C24 B1 C11 -59.8(3) . . . . ?
C24 C19 C20 C21 -0.8(3) . . . . ?
B1 N1 C5 C6 -176.76(16) . . . . ?
B1 N1 C5 C19 1.69(19) . . . . ?
B1 N1 C17 C18 176.49(18) . . . . ?
B1 C4 C10 C9 179.39(15) . . . . ?
B1 C4 C10 C16 -3.29(19) . . . . ?
B1 C11 C12 C13 -178.40(17) . . . . ?
B1 C11 C16 C10 4.12(19) . . . . ?
B1 C11 C16 C15 -178.99(15) . . . . ?

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

data_220525_ysg_hashizume_01_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2176259'
loop_
_audit_author_name
_audit_author_address
'yusuke yoshigoe'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-08-24 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-08-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H17 B F3 N'
_chemical_formula_sum            'C25 H17 B F3 N'
_chemical_formula_weight         399.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5923(5)
_cell_length_b                   10.4752(6)
_cell_length_c                   21.9452(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.678(2)
_cell_angle_gamma                90
_cell_volume                     1974.35(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5883
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.834
_cell_measurement_theta_min      3.06
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.997
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1110 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.9172.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_preparation       diffusion
_exptl_crystal_recrystallization_method diffusion
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.024
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22176
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         1.857
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_special_details          none
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3083
_reflns_number_total             3754
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         3754
_refine_ls_number_restraints     165
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.136
_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)+(0.0442P)²+0.7989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1111
_refine_special_details          none
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F2-F1 \\sim F2-F3 \\sim F1-F3 \\sim F2A-F3A \\sim F2A-F1A \\sim F3A-F1A
 with sigma of 0.04
 C9-C8 \\sim C9-F2 \\sim C9-F1 \\sim C9-F3 \\sim C9-F2A \\sim C9-F3A \\sim
C9-F1A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F3A, F1A, F2A, C9, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2, F1, F3, C9, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16, C15, C20, C18, C17, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C5, C14, C13, C2, C3, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C15, C16, C17, C18, C19, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(F2A)=Sof(F3A)=Sof(F1A)=1-FVAR(1)
 Sof(F2)=Sof(F1)=Sof(F3)=FVAR(1)
 Sof(C4A)=Sof(H4A)=Sof(C3A)=Sof(H3A)=Sof(C2A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=
 Sof(C5A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C16A)=Sof(C15A)=Sof(C17A)=
 Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=1-FVAR(2)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C5)=Sof(C14)=Sof(C13)=Sof(H13)=Sof(C2)=
 Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=
 Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(C15)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C3(H3), C4(H4), C6(H6), C7(H7), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C28(H28), C4A(H4A), C3A(H3A),
  C13A(H13A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A)
5.b Fitted hexagon refined as free rotating group:
 C5(C14,C13,C2,C3,C4), C16(C17,C18,C19,C20,C15)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N1 N 0.61475(14) 0.37635(12) 0.72913(6) 0.0283(3) Uani 1 1 d . . . . .
C1 C 0.7179(7) 0.7924(5) 0.9711(3) 0.0489(17) Uani 0.337(5) 1 d . . P A 1
H1A H 0.826908 0.811420 0.975569 0.073 Uiso 0.337(5) 1 calc R U P A 1
H1B H 0.678738 0.767331 1.009890 0.073 Uiso 0.337(5) 1 calc R U P A 1
H1C H 0.662992 0.866804 0.956695 0.073 Uiso 0.337(5) 1 calc R U P A 1
C5 C 0.645(2) 0.4943(17) 0.8449(8) 0.020(3) Uani 0.337(5) 1 d G . P A 1
C14 C 0.5375(19) 0.5173(17) 0.8896(9) 0.027(3) Uani 0.337(5) 1 d G . P A 1
C13 C 0.563(2) 0.6155(16) 0.9313(7) 0.024(2) Uani 0.337(5) 1 d G . P A 1
H13 H 0.490430 0.630860 0.961237 0.029 Uiso 0.337(5) 1 calc R U P A 1
C2 C 0.695(2) 0.6906(17) 0.9284(8) 0.031(3) Uani 0.337(5) 1 d G . P A 1
C3 C 0.803(2) 0.668(2) 0.8837(9) 0.034(3) Uani 0.337(5) 1 d G . P A 1
H3 H 0.892237 0.717936 0.881747 0.040 Uiso 0.337(5) 1 calc R U P A 1
C4 C 0.778(2) 0.570(2) 0.8419(8) 0.036(3) Uani 0.337(5) 1 d G . P A 1
H4 H 0.850432 0.554124 0.812027 0.043 Uiso 0.337(5) 1 calc R U P A 1
C6 C 0.56262(19) 0.47111(15) 0.69307(7) 0.0332(4) Uani 1 1 d . . . . .
H6 H 0.501873 0.535338 0.709427 0.040 Uiso 1 1 calc R U . . .
C7 C 0.59714(19) 0.47537(17) 0.63231(8) 0.0384(4) Uani 1 1 d . . . . .
H7 H 0.562163 0.542412 0.607728 0.046 Uiso 1 1 calc R U . . .
C8 C 0.68558(19) 0.37706(18) 0.60846(7) 0.0393(4) Uani 1 1 d D . . . .
C9 C 0.7305(3) 0.3820(2) 0.54320(9) 0.0606(6) Uani 1 1 d D . . . .
F2 F 0.8609(6) 0.4431(5) 0.53583(15) 0.0867(16) Uani 0.607(10) 1 d D . P B 1
F1 F 0.6214(7) 0.4208(9) 0.5063(2) 0.125(3) Uani 0.607(10) 1 d D . P B 1
F3 F 0.7645(5) 0.2606(4) 0.52309(18) 0.0706(11) Uani 0.607(10) 1 d D . P B 1
C16 C 0.4191(14) 0.3576(18) 0.8328(7) 0.018(2) Uani 0.337(5) 1 d G . P A 1
C17 C 0.2897(17) 0.2833(16) 0.8176(6) 0.031(3) Uani 0.337(5) 1 d G . P A 1
H17 H 0.291429 0.229224 0.784038 0.037 Uiso 0.337(5) 1 calc R U P A 1
C18 C 0.1576(14) 0.2899(16) 0.8526(7) 0.031(2) Uani 0.337(5) 1 d G . P A 1
H18 H 0.071025 0.240221 0.842405 0.038 Uiso 0.337(5) 1 calc R U P A 1
C19 C 0.1550(12) 0.3708(16) 0.9028(6) 0.031(2) Uani 0.337(5) 1 d G . P A 1
H19 H 0.066684 0.375163 0.926166 0.038 Uiso 0.337(5) 1 calc R U P A 1
C20 C 0.2845(14) 0.4450(15) 0.9180(7) 0.025(2) Uani 0.337(5) 1 d G . P A 1
H20 H 0.282750 0.499110 0.951561 0.030 Uiso 0.337(5) 1 calc R U P A 1
C15 C 0.4165(14) 0.4384(17) 0.8830(8) 0.021(2) Uani 0.337(5) 1 d G . P A 1
C21 C 0.69796(17) 0.23673(14) 0.81105(7) 0.0294(3) Uani 1 1 d . . . . .
C22 C 0.73752(19) 0.16521(15) 0.86294(7) 0.0347(4) Uani 1 1 d . . . . .
H22 H 0.709105 0.193775 0.901167 0.042 Uiso 1 1 calc R U . . .
C23 C 0.81919(19) 0.05153(16) 0.85758(8) 0.0389(4) Uani 1 1 d . . . . .
H23 H 0.845609 0.005039 0.892474 0.047 Uiso 1 1 calc R U . . .
C24 C 0.86206(19) 0.00609(16) 0.80112(8) 0.0390(4) Uani 1 1 d . . . . .
H24 H 0.915155 -0.070986 0.798461 0.047 Uiso 1 1 calc R U . . .
C25 C 0.82620(18) 0.07488(15) 0.74870(8) 0.0352(4) Uani 1 1 d . . . . .
H25 H 0.854653 0.045321 0.710652 0.042 Uiso 1 1 calc R U . . .
C26 C 0.74617(17) 0.18978(14) 0.75464(7) 0.0297(3) Uani 1 1 d . . . . .
C27 C 0.69930(17) 0.27835(14) 0.70621(7) 0.0295(3) Uani 1 1 d . . . . .
C28 C 0.73469(18) 0.27666(17) 0.64489(7) 0.0355(4) Uani 1 1 d . . . . .
H28 H 0.790395 0.209189 0.628696 0.043 Uiso 1 1 calc R U . . .
B1 B 0.5981(2) 0.36550(17) 0.80184(8) 0.0296(4) Uani 1 1 d . . . . .
F2A F 0.7712(12) 0.5061(7) 0.5268(2) 0.095(3) Uani 0.393(10) 1 d D . P B 2
F3A F 0.8277(14) 0.3028(12) 0.5249(4) 0.140(5) Uani 0.393(10) 1 d D . P B 2
F1A F 0.6006(9) 0.3784(7) 0.5067(3) 0.0699(18) Uani 0.393(10) 1 d D . P B 2
C4A C 0.2981(10) 0.2798(8) 0.8067(4) 0.0311(12) Uani 0.663(5) 1 d . . P A 2
H4A H 0.303315 0.226027 0.773063 0.037 Uiso 0.663(5) 1 calc R U P A 2
C3A C 0.1638(10) 0.2825(8) 0.8397(4) 0.0417(16) Uani 0.663(5) 1 d . . P A 2
H3A H 0.079618 0.232201 0.827075 0.050 Uiso 0.663(5) 1 calc R U P A 2
C2A C 0.1510(8) 0.3583(9) 0.8912(4) 0.0474(19) Uani 0.663(5) 1 d . . P A 2
C13A C 0.2745(11) 0.4383(9) 0.9074(4) 0.044(2) Uani 0.663(5) 1 d . . P A 2
H13A H 0.267544 0.491603 0.941138 0.053 Uiso 0.663(5) 1 calc R U P A 2
C14A C 0.4086(9) 0.4387(10) 0.8733(5) 0.0315(16) Uani 0.663(5) 1 d . . P A 2
C5A C 0.4259(10) 0.3557(10) 0.8225(4) 0.0291(15) Uani 0.663(5) 1 d . . P A 2
C1A C 0.0206(3) 0.3613(3) 0.93931(13) 0.0483(9) Uani 0.663(5) 1 d . . P A 2
H1AA H -0.074021 0.393257 0.920625 0.072 Uiso 0.663(5) 1 calc R U P A 2
H1AB H 0.052169 0.416047 0.972526 0.072 Uiso 0.663(5) 1 calc R U P A 2
H1AC H 0.003603 0.276584 0.954357 0.072 Uiso 0.663(5) 1 calc R U P A 2
C16A C 0.6661(13) 0.4875(10) 0.8355(4) 0.0264(15) Uani 0.663(5) 1 d . . P A 2
C15A C 0.5596(10) 0.5195(8) 0.8810(4) 0.0250(13) Uani 0.663(5) 1 d . . P A 2
C17A C 0.7991(10) 0.5613(10) 0.8325(4) 0.0292(11) Uani 0.663(5) 1 d . . P A 2
H17A H 0.871022 0.543471 0.802816 0.035 Uiso 0.663(5) 1 calc R U P A 2
C18A C 0.8279(12) 0.6611(11) 0.8726(5) 0.0376(16) Uani 0.663(5) 1 d . . P A 2
H18A H 0.916242 0.711319 0.868345 0.045 Uiso 0.663(5) 1 calc R U P A 2
C19A C 0.7273(12) 0.6869(9) 0.9187(4) 0.0379(18) Uani 0.663(5) 1 d . . P A 2
H19A H 0.749671 0.751830 0.946553 0.046 Uiso 0.663(5) 1 calc R U P A 2
C20A C 0.5923(11) 0.6154(10) 0.9234(4) 0.0364(15) Uani 0.663(5) 1 d . . P A 2
H20A H 0.524053 0.631357 0.954661 0.044 Uiso 0.663(5) 1 calc R U P A 2


_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
N1 C6 1.3385(19) . ?
N1 C27 1.3623(19) . ?
N1 B1 1.610(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.429(15) . ?
C5 C14 1.3900 . ?
C5 C4 1.3900 . ?
C5 B1 1.690(14) . ?
C14 C13 1.3900 . ?
C14 C15 1.333(19) . ?
C13 H13 0.9300 . ?
C13 C2 1.3900 . ?
C2 C3 1.3900 . ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.375(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(2) . ?
C8 C9 1.495(2) . ?
C8 C28 1.380(2) . ?
C9 F2 1.304(4) . ?
C9 F1 1.286(5) . ?
C9 F3 1.380(4) . ?
C9 F2A 1.396(6) . ?
C9 F3A 1.252(6) . ?
C9 F1A 1.355(7) . ?
C16 C17 1.3900 . ?
C16 C15 1.3900 . ?
C16 B1 1.701(11) . ?
C17 H17 0.9300 . ?
C17 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
C20 H20 0.9300 . ?
C20 C15 1.3900 . ?
C21 C22 1.397(2) . ?
C21 C26 1.406(2) . ?
C21 B1 1.608(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.389(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.387(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.394(2) . ?
C26 C27 1.459(2) . ?
C27 C28 1.388(2) . ?
C28 H28 0.9300 . ?
B1 C5A 1.563(8) . ?
B1 C16A 1.579(10) . ?
C4A H4A 0.9300 . ?
C4A C3A 1.381(4) . ?
C4A C5A 1.392(4) . ?
C3A H3A 0.9300 . ?
C3A C2A 1.388(5) . ?
C2A C13A 1.390(5) . ?
C2A C1A 1.563(8) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.393(4) . ?
C14A C5A 1.424(4) . ?
C14A C15A 1.554(10) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C16A C15A 1.415(6) . ?
C16A C17A 1.383(5) . ?
C15A C20A 1.392(5) . ?
C17A H17A 0.9300 . ?
C17A C18A 1.384(5) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.378(6) . ?
C19A H19A 0.9300 . ?
C19A C20A 1.388(6) . ?
C20A H20A 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
C6 N1 C27 120.89(13) . . ?
C6 N1 B1 126.89(13) . . ?
C27 N1 B1 112.12(12) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C14 C5 C4 120.0 . . ?
C14 C5 B1 112.2(10) . . ?
C4 C5 B1 127.7(10) . . ?
C13 C14 C5 120.0 . . ?
C15 C14 C5 110.5(14) . . ?
C15 C14 C13 129.4(14) . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C2 120.0 . . ?
C2 C13 H13 120.0 . . ?
C13 C2 C1 119.2(11) . . ?
C3 C2 C1 120.8(11) . . ?
C3 C2 C13 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C6 H6 119.4 . . ?
N1 C6 C7 121.29(15) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.8 . . ?
C6 C7 C8 118.45(15) . . ?
C8 C7 H7 120.8 . . ?
C7 C8 C9 119.59(16) . . ?
C28 C8 C7 120.49(16) . . ?
C28 C8 C9 119.90(17) . . ?
F2 C9 C8 112.5(2) . . ?
F2 C9 F3 102.8(3) . . ?
F1 C9 C8 114.2(3) . . ?
F1 C9 F2 112.3(4) . . ?
F1 C9 F3 104.3(4) . . ?
F3 C9 C8 109.7(2) . . ?
F2A C9 C8 110.7(3) . . ?
F3A C9 C8 118.5(4) . . ?
F3A C9 F2A 111.1(5) . . ?
F3A C9 F1A 109.8(7) . . ?
F1A C9 C8 109.5(4) . . ?
F1A C9 F2A 94.7(5) . . ?
C17 C16 C15 120.0 . . ?
C17 C16 B1 131.1(9) . . ?
C15 C16 B1 108.8(9) . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C15 120.0 . . ?
C15 C20 H20 120.0 . . ?
C14 C15 C16 115.6(13) . . ?
C14 C15 C20 123.8(13) . . ?
C20 C15 C16 120.0 . . ?
C22 C21 C26 117.35(14) . . ?
C22 C21 B1 131.95(14) . . ?
C26 C21 B1 110.65(13) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.15(15) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.19(15) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.33(16) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 121.0 . . ?
C24 C25 C26 118.04(16) . . ?
C26 C25 H25 121.0 . . ?
C21 C26 C27 109.69(13) . . ?
C25 C26 C21 122.90(14) . . ?
C25 C26 C27 127.41(14) . . ?
N1 C27 C26 110.44(13) . . ?
N1 C27 C28 120.12(14) . . ?
C28 C27 C26 129.38(14) . . ?
C8 C28 C27 118.69(15) . . ?
C8 C28 H28 120.7 . . ?
C27 C28 H28 120.7 . . ?
N1 B1 C5 118.1(7) . . ?
N1 B1 C16 120.5(6) . . ?
C5 B1 C16 91.2(8) . . ?
C21 B1 N1 96.95(12) . . ?
C21 B1 C5 118.8(8) . . ?
C21 B1 C16 113.2(7) . . ?
C5A B1 N1 113.9(4) . . ?
C5A B1 C21 114.5(4) . . ?
C5A B1 C16A 104.9(5) . . ?
C16A B1 N1 111.3(4) . . ?
C16A B1 C21 115.5(4) . . ?
C3A C4A H4A 119.2 . . ?
C3A C4A C5A 121.5(3) . . ?
C5A C4A H4A 119.2 . . ?
C4A C3A H3A 119.1 . . ?
C4A C3A C2A 121.7(3) . . ?
C2A C3A H3A 119.1 . . ?
C3A C2A C13A 118.4(3) . . ?
C3A C2A C1A 129.6(5) . . ?
C13A C2A C1A 111.8(6) . . ?
C2A C13A H13A 120.0 . . ?
C2A C13A C14A 120.0(3) . . ?
C14A C13A H13A 120.0 . . ?
C13A C14A C5A 121.7(3) . . ?
C13A C14A C15A 130.1(7) . . ?
C5A C14A C15A 108.2(7) . . ?
C4A C5A B1 135.3(6) . . ?
C4A C5A C14A 116.4(3) . . ?
C14A C5A B1 108.0(6) . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C15A C16A B1 106.5(6) . . ?
C17A C16A B1 136.5(6) . . ?
C17A C16A C15A 116.9(4) . . ?
C16A C15A C14A 110.4(7) . . ?
C20A C15A C14A 128.1(8) . . ?
C20A C15A C16A 121.4(4) . . ?
C16A C17A H17A 119.2 . . ?
C16A C17A C18A 121.7(5) . . ?
C18A C17A H17A 119.2 . . ?
C17A C18A H18A 119.6 . . ?
C19A C18A C17A 120.7(4) . . ?
C19A C18A H18A 119.6 . . ?
C18A C19A H19A 120.2 . . ?
C18A C19A C20A 119.5(4) . . ?
C20A C19A H19A 120.2 . . ?
C15A C20A H20A 120.2 . . ?
C19A C20A C15A 119.5(4) . . ?
C19A C20A H20A 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C6 C7 C8 1.3(3) . . . . ?
N1 C27 C28 C8 1.4(2) . . . . ?
N1 B1 C5A C4A 51.2(9) . . . . ?
N1 B1 C5A C14A -135.6(4) . . . . ?
N1 B1 C16A C15A 137.5(4) . . . . ?
N1 B1 C16A C17A -45.8(11) . . . . ?
C1 C2 C3 C4 -179.0(18) . . . . ?
C5 C14 C13 C2 0.0 . . . . ?
C5 C14 C15 C16 -3.3(16) . . . . ?
C5 C14 C15 C20 -174.8(10) . . . . ?
C14 C5 C4 C3 0.0 . . . . ?
C14 C5 B1 N1 136.2(7) . . . . ?
C14 C5 B1 C16 10.3(10) . . . . ?
C14 C5 B1 C21 -107.1(8) . . . . ?
C14 C13 C2 C1 179.0(18) . . . . ?
C14 C13 C2 C3 0.0 . . . . ?
C13 C14 C15 C16 174.0(13) . . . . ?
C13 C14 C15 C20 3(3) . . . . ?
C13 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C4 C5 C14 C13 0.0 . . . . ?
C4 C5 C14 C15 177.6(19) . . . . ?
C4 C5 B1 N1 -47.7(16) . . . . ?
C4 C5 B1 C16 -173.6(15) . . . . ?
C4 C5 B1 C21 69.0(15) . . . . ?
C6 N1 C27 C26 178.30(13) . . . . ?
C6 N1 C27 C28 1.0(2) . . . . ?
C6 N1 B1 C5 -47.9(8) . . . . ?
C6 N1 B1 C16 62.1(8) . . . . ?
C6 N1 B1 C21 -175.75(14) . . . . ?
C6 N1 B1 C5A 63.6(5) . . . . ?
C6 N1 B1 C16A -54.8(5) . . . . ?
C6 C7 C8 C9 -177.44(18) . . . . ?
C6 C7 C8 C28 1.2(3) . . . . ?
C7 C8 C9 F2 88.3(4) . . . . ?
C7 C8 C9 F1 -41.3(6) . . . . ?
C7 C8 C9 F3 -158.0(3) . . . . ?
C7 C8 C9 F2A 40.0(6) . . . . ?
C7 C8 C9 F3A 170.1(9) . . . . ?
C7 C8 C9 F1A -63.1(4) . . . . ?
C7 C8 C28 C27 -2.5(3) . . . . ?
C9 C8 C28 C27 176.14(17) . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C17 C16 C15 C14 -171.9(18) . . . . ?
C17 C16 C15 C20 0.0 . . . . ?
C17 C16 B1 N1 47.6(14) . . . . ?
C17 C16 B1 C5 171.5(14) . . . . ?
C17 C16 B1 C21 -66.3(13) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C15 0.0 . . . . ?
C19 C20 C15 C14 171(2) . . . . ?
C19 C20 C15 C16 0.0 . . . . ?
C15 C14 C13 C2 -177(2) . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C15 C16 B1 N1 -135.6(6) . . . . ?
C15 C16 B1 C5 -11.6(10) . . . . ?
C15 C16 B1 C21 110.5(7) . . . . ?
C21 C22 C23 C24 -0.5(2) . . . . ?
C21 C26 C27 N1 -3.64(17) . . . . ?
C21 C26 C27 C28 173.32(16) . . . . ?
C21 B1 C5A C4A -59.1(9) . . . . ?
C21 B1 C5A C14A 114.1(4) . . . . ?
C21 B1 C16A C15A -113.2(4) . . . . ?
C21 B1 C16A C17A 63.5(11) . . . . ?
C22 C21 C26 C25 2.0(2) . . . . ?
C22 C21 C26 C27 -178.16(13) . . . . ?
C22 C21 B1 N1 179.85(15) . . . . ?
C22 C21 B1 C5 52.4(7) . . . . ?
C22 C21 B1 C16 -52.7(6) . . . . ?
C22 C21 B1 C5A -59.9(4) . . . . ?
C22 C21 B1 C16A 62.2(5) . . . . ?
C22 C23 C24 C25 1.1(3) . . . . ?
C23 C24 C25 C26 -0.2(2) . . . . ?
C24 C25 C26 C21 -1.4(2) . . . . ?
C24 C25 C26 C27 178.75(15) . . . . ?
C25 C26 C27 N1 176.22(14) . . . . ?
C25 C26 C27 C28 -6.8(3) . . . . ?
C26 C21 C22 C23 -1.0(2) . . . . ?
C26 C21 B1 N1 -2.80(15) . . . . ?
C26 C21 B1 C5 -130.2(7) . . . . ?
C26 C21 B1 C16 124.7(6) . . . . ?
C26 C21 B1 C5A 117.4(4) . . . . ?
C26 C21 B1 C16A -120.4(4) . . . . ?
C26 C27 C28 C8 -175.30(16) . . . . ?
C27 N1 C6 C7 -2.4(2) . . . . ?
C27 N1 B1 C5 128.5(8) . . . . ?
C27 N1 B1 C16 -121.6(7) . . . . ?
C27 N1 B1 C21 0.61(15) . . . . ?
C27 N1 B1 C5A -120.1(4) . . . . ?
C27 N1 B1 C16A 121.5(4) . . . . ?
C28 C8 C9 F2 -90.4(4) . . . . ?
C28 C8 C9 F1 140.0(5) . . . . ?
C28 C8 C9 F3 23.4(3) . . . . ?
C28 C8 C9 F2A -138.6(5) . . . . ?
C28 C8 C9 F3A -8.6(9) . . . . ?
C28 C8 C9 F1A 118.3(4) . . . . ?
B1 N1 C6 C7 173.69(15) . . . . ?
B1 N1 C27 C26 1.69(17) . . . . ?
B1 N1 C27 C28 -175.60(14) . . . . ?
B1 C5 C14 C13 176.4(15) . . . . ?
B1 C5 C14 C15 -5.9(14) . . . . ?
B1 C5 C4 C3 -175.8(18) . . . . ?
B1 C16 C17 C18 176.6(15) . . . . ?
B1 C16 C15 C14 10.8(14) . . . . ?
B1 C16 C15 C20 -177.3(12) . . . . ?
B1 C21 C22 C23 176.23(15) . . . . ?
B1 C21 C26 C25 -175.82(14) . . . . ?
B1 C21 C26 C27 4.05(17) . . . . ?
B1 C16A C15A C14A -9.3(7) . . . . ?
B1 C16A C15A C20A 173.4(8) . . . . ?
B1 C16A C17A C18A -175.8(12) . . . . ?
C4A C3A C2A C13A 3.6(5) . . . . ?
C4A C3A C2A C1A -170.7(7) . . . . ?
C3A C4A C5A B1 170.9(9) . . . . ?
C3A C4A C5A C14A -1.9(5) . . . . ?
C3A C2A C13A C14A -1.6(5) . . . . ?
C2A C13A C14A C5A -2.1(5) . . . . ?
C2A C13A C14A C15A 178.8(11) . . . . ?
C13A C14A C5A B1 -170.9(7) . . . . ?
C13A C14A C5A C4A 3.8(5) . . . . ?
C13A C14A C15A C16A 179.9(7) . . . . ?
C13A C14A C15A C20A -2.9(14) . . . . ?
C14A C15A C20A C19A -172.6(11) . . . . ?
C5A B1 C16A C15A 13.9(6) . . . . ?
C5A B1 C16A C17A -169.4(9) . . . . ?
C5A C4A C3A C2A -1.8(5) . . . . ?
C5A C14A C15A C16A 0.7(7) . . . . ?
C5A C14A C15A C20A 177.8(7) . . . . ?
C1A C2A C13A C14A 173.6(6) . . . . ?
C16A B1 C5A C4A 173.2(8) . . . . ?
C16A B1 C5A C14A -13.6(6) . . . . ?
C16A C15A C20A C19A 4.2(5) . . . . ?
C16A C17A C18A C19A 2.7(5) . . . . ?
C15A C14A C5A B1 8.4(7) . . . . ?
C15A C14A C5A C4A -176.9(8) . . . . ?
C15A C16A C17A C18A 0.7(5) . . . . ?
C17A C16A C15A C14A 173.2(9) . . . . ?
C17A C16A C15A C20A -4.2(5) . . . . ?
C17A C18A C19A C20A -2.7(5) . . . . ?
C18A C19A C20A C15A -0.7(5) . . . . ?

_olex2_exptl_crystal_mounting_method cryoroop
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_220525_ysg_hashizume_02_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2203031'
loop_
_audit_author_name
_audit_author_address
'Yusuke Yoshigoe'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-08-23 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_audit_creation_date             2022-08-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19.822 B N'
_chemical_formula_sum            'C25 H19.82 B N'
_chemical_formula_weight         345.05
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.386(4)
_cell_length_b                   8.564(2)
_cell_length_c                   12.291(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.445(7)
_cell_angle_gamma                90
_cell_volume                     1846.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5032
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.797
_cell_measurement_theta_min      2.647
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1208 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.8039.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             727
_exptl_crystal_preparation       diffusion
_exptl_crystal_recrystallization_method diffusion
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14991
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.647
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_special_details          none
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2647
_reflns_number_total             3173
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3173
_refine_ls_number_restraints     210
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      1.032
_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)+(0.0579P)²+1.9580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1510
_refine_ls_wR_factor_ref         0.1573
_refine_special_details          none
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C0) \\sim Ueq, Uanis(N0) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 C007, C00H, C00L, C00K, C00C, C008
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C0, B00Q, C1, C2, N0
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C0, C003, C004, C00I, C00O, C00N
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 B00Q, C0, C1, N0, C2
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C001, C009, C00A, C00G, C00E, C00B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N0, C00B, C00E, C00G, C00A, C009
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C005, C00J, C00M, C00D, C00F, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C2, C008, C00C, C00K, C00L, C00H
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H00A)=Sof(H00G)=Sof(H00H)=Sof(N0)=Sof(C0)=Sof(H00R)=Sof(C1)=Sof(C2)=
 Sof(H00X)=Sof(C3)=Sof(H3A)=Sof(H3B)=1-FVAR(1)
 Sof(C001)=Sof(H00B)=Sof(N002)=Sof(C006)=Sof(H00F)=Sof(C007)=Sof(C00R)=
 Sof(H00N)=Sof(H00O)=Sof(H00P)=Sof(H00Q)=Sof(H00U)=Sof(H00W)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00B(H00A), C00E(H00E), C00G(H00G), C00A(H00C), C00J(H00J),
 C00M(H00M), C00D(H00D), C00F(H00F), C00F(H00H), C00N(H00Q), C00N(H00R),
 C00O(H00S), C004(H004), C00C(H00T), C00K(H00U), C00L(H00V), C00H(H00W),
 C00H(H00X)
5.b Fitted hexagon refined as free rotating group:
 C001(C00B,C00E,C00G,C00A,C009), C006(C005,C00J,C00M,C00D,C00F), C0(C00N,C00O,
 C00I,C004,C003), C2(C008,C00C,C00K,C00L,C00H)
5.c X=CH2 refined with riding coordinates:
 C3(H3A,H3B)
5.d Idealised Me refined as rotating group:
 C00P(H00I,H00K,H00L), C00R(H00N,H00O,H00P)
;
_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
C001 C 0.33374(8) 0.3647(3) 0.64109(14) 0.0263(13) Uani 0.822(7) 1 d G . P A 1
C00B C 0.35393(9) 0.3054(2) 0.75141(15) 0.0377(6) Uani 1 1 d G . . . .
H00B H 0.320441 0.240610 0.773821 0.045 Uiso 0.822(7) 1 calc R U P A 1
H00A H 0.321488 0.238406 0.774283 0.045 Uiso 0.178(7) 1 calc R U P A 2
C00E C 0.42417(9) 0.3431(2) 0.82823(11) 0.0384(6) Uani 1 1 d G . . . .
H00E H 0.437673 0.303452 0.902042 0.046 Uiso 1 1 calc R U . . .
C00G C 0.47422(7) 0.4400(2) 0.79474(12) 0.0391(6) Uani 1 1 d G . . . .
H00G H 0.521211 0.465181 0.846135 0.047 Uiso 0.178(7) 1 calc R U P A 2
C00A C 0.45403(8) 0.49924(19) 0.68442(13) 0.0368(6) Uani 1 1 d G . . . .
H00C H 0.487518 0.564070 0.662006 0.044 Uiso 1 1 calc R U . . .
C009 C 0.38379(9) 0.4616(2) 0.60759(11) 0.0311(5) Uani 1 1 d G . . . .
N002 N 0.18454(14) 0.4053(3) 0.5829(2) 0.0383(11) Uani 0.822(7) 1 d . . P A 1
C006 C 0.22289(10) 0.16786(16) 0.50724(19) 0.0295(15) Uani 0.822(7) 1 d G . P A
1
C005 C 0.15302(9) 0.14958(16) 0.52775(16) 0.0289(5) Uani 1 1 d G . . . .
C00J C 0.11478(7) 0.00768(18) 0.50470(14) 0.0331(6) Uani 1 1 d G . . . .
H00J H 0.068035 -0.004545 0.518422 0.040 Uiso 1 1 calc R U . . .
C00M C 0.14639(8) -0.11594(14) 0.46113(15) 0.0342(6) Uani 1 1 d G . . . .
H00M H 0.120804 -0.210878 0.445708 0.041 Uiso 1 1 calc R U . . .
C00D C 0.21626(8) -0.09766(16) 0.44062(14) 0.0343(6) Uani 1 1 d G . . . .
H00D H 0.237409 -0.180372 0.411473 0.041 Uiso 1 1 calc R U . . .
C00F C 0.25450(8) 0.0442(2) 0.46368(17) 0.0340(6) Uani 1 1 d G . . . .
H00F H 0.301247 0.056468 0.449952 0.041 Uiso 0.822(7) 1 calc R U P A 1
H00H H 0.300689 0.050163 0.447450 0.041 Uiso 0.178(7) 1 calc R U P A 2
C007 C 0.27441(16) 0.4502(4) 0.4459(3) 0.0311(19) Uani 0.822(7) 1 d . . P A 1
C00P C -0.01632(14) 0.5000(3) 0.6840(2) 0.0404(6) Uani 1 1 d . . . . .
H00I H -0.061012 0.469092 0.624353 0.061 Uiso 1 1 calc R U . . .
H00K H -0.018897 0.609740 0.698484 0.061 Uiso 1 1 calc R U . . .
H00L H -0.013569 0.442465 0.752115 0.061 Uiso 1 1 calc R U . . .
B00Q B 0.25434(15) 0.3449(4) 0.5411(2) 0.0342(6) Uani 1 1 d . . . . .
C00R C 0.54959(17) 0.4833(5) 0.8783(3) 0.0500(11) Uani 0.822(7) 1 d . . P A 1
H00N H 0.548558 0.461006 0.954413 0.075 Uiso 0.822(7) 1 calc R U P A 1
H00O H 0.558880 0.592665 0.871662 0.075 Uiso 0.822(7) 1 calc R U P A 1
H00P H 0.589471 0.423872 0.862355 0.075 Uiso 0.822(7) 1 calc R U P A 1
N0 N 0.3309(7) 0.3654(17) 0.6413(11) 0.030(5) Uani 0.178(7) 1 d . U P A 2
C0 C 0.18401(9) 0.4049(2) 0.58317(19) 0.032(4) Uani 0.178(7) 1 d G U P A 2
C00N C 0.17369(9) 0.55144(18) 0.62492(17) 0.0392(6) Uani 1 1 d G . . . .
H00Q H 0.210125 0.629106 0.631556 0.047 Uiso 0.822(7) 1 calc R U P A 1
H00R H 0.210207 0.628872 0.631316 0.047 Uiso 0.178(7) 1 calc R U P A 2
C00O C 0.10881(9) 0.58224(14) 0.65710(14) 0.0372(6) Uani 1 1 d G . . . .
H00S H 0.101911 0.680269 0.685034 0.045 Uiso 1 1 calc R U . . .
C00I C 0.05424(7) 0.46651(17) 0.64754(15) 0.0325(5) Uani 1 1 d G . . . .
C004 C 0.06455(7) 0.31999(15) 0.60580(14) 0.0303(5) Uani 1 1 d G . . . .
H004 H 0.028035 0.242560 0.599400 0.036 Uiso 1 1 calc R U . . .
C003 C 0.12943(9) 0.28919(16) 0.57361(16) 0.0292(5) Uani 1 1 d G . . . .
C1 C 0.2311(12) 0.182(2) 0.5093(16) 0.028(5) Uani 0.178(7) 1 d . . P A 2
C2 C 0.27656(10) 0.4515(2) 0.44496(15) 0.032(9) Uani 0.178(7) 1 d G . P A 2
C008 C 0.34950(9) 0.5117(2) 0.49151(11) 0.0311(5) Uani 1 1 d G . . . .
C00C C 0.38117(7) 0.6071(2) 0.42615(13) 0.0368(6) Uani 1 1 d G . . . .
H00T H 0.429972 0.647437 0.457291 0.044 Uiso 1 1 calc R U . . .
C00K C 0.33990(9) 0.6422(2) 0.31425(12) 0.0401(6) Uani 1 1 d G . . . .
H00U H 0.361092 0.706050 0.270526 0.048 Uiso 0.822(7) 1 calc R U P A 1
C00L C 0.26696(8) 0.5820(2) 0.26771(11) 0.0381(6) Uani 1 1 d G . . . .
H00V H 0.239349 0.605468 0.192842 0.046 Uiso 1 1 calc R U . . .
C00H C 0.23529(7) 0.4866(2) 0.33306(15) 0.0366(6) Uani 1 1 d G . . . .
H00W H 0.186685 0.445981 0.300578 0.044 Uiso 0.822(7) 1 calc R U P A 1
H00X H 0.186484 0.446270 0.301922 0.044 Uiso 0.178(7) 1 calc R U P A 2
C3 C 0.3663(11) 0.746(2) 0.2549(17) 0.069(6) Uani 0.178(7) 1 d . . P A 2
H3A H 0.336008 0.777749 0.183198 0.083 Uiso 0.178(7) 1 calc R U P A 2
H3B H 0.415004 0.787433 0.285116 0.083 Uiso 0.178(7) 1 calc R U P A 2


_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
C001 C00B 1.3900 . ?
C001 C009 1.3900 . ?
C001 B00Q 1.611(3) . ?
C00B H00B 0.9300 . ?
C00B H00A 0.9300 . ?
C00B C00E 1.3900 . ?
C00B N0 1.390(15) . ?
C00E H00E 0.9300 . ?
C00E C00G 1.3900 . ?
C00G H00G 0.9300 . ?
C00G C00A 1.3900 . ?
C00G C00R 1.503(3) . ?
C00A H00C 0.9300 . ?
C00A C009 1.3900 . ?
C009 N0 1.427(13) . ?
C009 C008 1.4417(17) . ?
N002 B00Q 1.604(4) . ?
N002 C00N 1.391(3) . ?
N002 C003 1.400(3) . ?
C006 C005 1.3900 . ?
C006 C00F 1.3900 . ?
C006 B00Q 1.632(3) . ?
C005 C00J 1.3900 . ?
C005 C003 1.4429(16) . ?
C005 C1 1.54(2) . ?
C00J H00J 0.9300 . ?
C00J C00M 1.3900 . ?
C00M H00M 0.9300 . ?
C00M C00D 1.3900 . ?
C00D H00D 0.9300 . ?
C00D C00F 1.3900 . ?
C00F H00F 0.9300 . ?
C00F H00H 0.9300 . ?
C00F C1 1.425(18) . ?
C007 B00Q 1.605(4) . ?
C007 C008 1.426(3) . ?
C007 C00H 1.393(4) . ?
C00P H00I 0.9600 . ?
C00P H00K 0.9600 . ?
C00P H00L 0.9600 . ?
C00P C00I 1.521(3) . ?
B00Q N0 1.578(12) . ?
B00Q C0 1.614(3) . ?
B00Q C1 1.48(2) . ?
B00Q C2 1.638(3) . ?
C00R H00N 0.9600 . ?
C00R H00O 0.9600 . ?
C00R H00P 0.9600 . ?
C0 C00N 1.3900 . ?
C0 C003 1.3900 . ?
C00N H00Q 0.9300 . ?
C00N H00R 0.9300 . ?
C00N C00O 1.3900 . ?
C00O H00S 0.9300 . ?
C00O C00I 1.3900 . ?
C00I C004 1.3900 . ?
C004 H004 0.9300 . ?
C004 C003 1.3900 . ?
C2 C008 1.3900 . ?
C2 C00H 1.3900 . ?
C008 C00C 1.3900 . ?
C00C H00T 0.9300 . ?
C00C C00K 1.3900 . ?
C00K H00U 0.9300 . ?
C00K C00L 1.3900 . ?
C00K C3 1.332(17) . ?
C00L H00V 0.9300 . ?
C00L C00H 1.3900 . ?
C00H H00W 0.9300 . ?
C00H H00X 0.9300 . ?
C3 H3A 0.9300 . ?
C3 H3B 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
C00B C001 C009 120.0 . . ?
C00B C001 B00Q 128.46(14) . . ?
C009 C001 B00Q 111.45(14) . . ?
C001 C00B H00B 120.0 . . ?
C00E C00B C001 120.0 . . ?
C00E C00B H00B 120.0 . . ?
C00E C00B H00A 119.2 . . ?
C00E C00B N0 121.7(5) . . ?
N0 C00B H00A 119.2 . . ?
C00B C00E H00E 120.0 . . ?
C00B C00E C00G 120.0 . . ?
C00G C00E H00E 120.0 . . ?
C00E C00G H00G 120.0 . . ?
C00E C00G C00R 120.08(17) . . ?
C00A C00G C00E 120.0 . . ?
C00A C00G H00G 120.0 . . ?
C00A C00G C00R 119.91(18) . . ?
C00G C00A H00C 120.0 . . ?
C009 C00A C00G 120.0 . . ?
C009 C00A H00C 120.0 . . ?
C001 C009 C008 109.82(12) . . ?
C00A C009 C001 120.0 . . ?
C00A C009 N0 120.8(5) . . ?
C00A C009 C008 130.15(12) . . ?
N0 C009 C008 109.0(5) . . ?
C00N N002 B00Q 128.8(2) . . ?
C00N N002 C003 119.2(2) . . ?
C003 N002 B00Q 112.0(2) . . ?
C005 C006 C00F 120.0 . . ?
C005 C006 B00Q 109.55(13) . . ?
C00F C006 B00Q 130.45(14) . . ?
C006 C005 C003 112.33(12) . . ?
C00J C005 C006 120.0 . . ?
C00J C005 C003 127.67(12) . . ?
C00J C005 C1 124.2(7) . . ?
C003 C005 C1 108.1(7) . . ?
C005 C00J H00J 120.0 . . ?
C00M C00J C005 120.0 . . ?
C00M C00J H00J 120.0 . . ?
C00J C00M H00M 120.0 . . ?
C00J C00M C00D 120.0 . . ?
C00D C00M H00M 120.0 . . ?
C00M C00D H00D 120.0 . . ?
C00F C00D C00M 120.0 . . ?
C00F C00D H00D 120.0 . . ?
C006 C00F H00F 120.0 . . ?
C00D C00F C006 120.0 . . ?
C00D C00F H00F 120.0 . . ?
C00D C00F H00H 116.3 . . ?
C00D C00F C1 127.5(9) . . ?
C1 C00F H00H 116.3 . . ?
C008 C007 B00Q 109.2(2) . . ?
C00H C007 B00Q 133.5(2) . . ?
C00H C007 C008 117.3(2) . . ?
H00I C00P H00K 109.5 . . ?
H00I C00P H00L 109.5 . . ?
H00K C00P H00L 109.5 . . ?
C00I C00P H00I 109.5 . . ?
C00I C00P H00K 109.5 . . ?
C00I C00P H00L 109.5 . . ?
C001 B00Q C006 117.6(2) . . ?
N002 B00Q C001 110.5(2) . . ?
N002 B00Q C006 97.16(18) . . ?
N002 B00Q C007 115.7(2) . . ?
C007 B00Q C001 98.25(18) . . ?
C007 B00Q C006 118.5(2) . . ?
N0 B00Q C0 109.1(5) . . ?
N0 B00Q C2 98.3(5) . . ?
C0 B00Q C2 116.8(2) . . ?
C1 B00Q N0 115.5(9) . . ?
C1 B00Q C0 100.9(8) . . ?
C1 B00Q C2 116.8(7) . . ?
C00G C00R H00N 109.5 . . ?
C00G C00R H00O 109.5 . . ?
C00G C00R H00P 109.5 . . ?
H00N C00R H00O 109.5 . . ?
H00N C00R H00P 109.5 . . ?
H00O C00R H00P 109.5 . . ?
C00B N0 C009 117.5(8) . . ?
C00B N0 B00Q 131.2(9) . . ?
C009 N0 B00Q 111.3(9) . . ?
C00N C0 B00Q 128.08(14) . . ?
C00N C0 C003 120.0 . . ?
C003 C0 B00Q 111.92(14) . . ?
N002 C00N H00Q 119.8 . . ?
C0 C00N H00R 120.0 . . ?
C00O C00N N002 120.48(12) . . ?
C00O C00N C0 120.0 . . ?
C00O C00N H00Q 119.8 . . ?
C00O C00N H00R 120.0 . . ?
C00N C00O H00S 120.0 . . ?
C00N C00O C00I 120.0 . . ?
C00I C00O H00S 120.0 . . ?
C00O C00I C00P 119.88(14) . . ?
C004 C00I C00P 120.12(14) . . ?
C004 C00I C00O 120.0 . . ?
C00I C004 H004 120.0 . . ?
C003 C004 C00I 120.0 . . ?
C003 C004 H004 120.0 . . ?
N002 C003 C005 108.99(16) . . ?
C0 C003 C005 109.26(12) . . ?
C004 C003 N002 120.28(13) . . ?
C004 C003 C005 130.74(12) . . ?
C004 C003 C0 120.0 . . ?
C00F C1 C005 108.3(14) . . ?
C00F C1 B00Q 141.9(16) . . ?
B00Q C1 C005 109.7(11) . . ?
C008 C2 B00Q 109.17(14) . . ?
C008 C2 C00H 120.0 . . ?
C00H C2 B00Q 130.83(14) . . ?
C007 C008 C009 111.31(17) . . ?
C2 C008 C009 112.24(12) . . ?
C00C C008 C009 127.76(12) . . ?
C00C C008 C007 120.93(14) . . ?
C00C C008 C2 120.0 . . ?
C008 C00C H00T 120.0 . . ?
C008 C00C C00K 120.0 . . ?
C00K C00C H00T 120.0 . . ?
C00C C00K H00U 120.0 . . ?
C00L C00K C00C 120.0 . . ?
C00L C00K H00U 120.0 . . ?
C3 C00K C00C 120.4(9) . . ?
C3 C00K C00L 119.2(9) . . ?
C00K C00L H00V 120.0 . . ?
C00H C00L C00K 120.0 . . ?
C00H C00L H00V 120.0 . . ?
C007 C00H H00W 119.1 . . ?
C2 C00H H00X 120.0 . . ?
C00L C00H C007 121.75(14) . . ?
C00L C00H C2 120.0 . . ?
C00L C00H H00W 119.1 . . ?
C00L C00H H00X 120.0 . . ?
C00K C3 H3A 120.0 . . ?
C00K C3 H3B 120.0 . . ?
H3A C3 H3B 120.0 . . ?

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
C001 C00B C00E C00G 0.0 . . . . ?
C001 C009 C008 C007 1.0(2) . . . . ?
C001 C009 C008 C00C -178.95(14) . . . . ?
C00B C001 C009 C00A 0.0 . . . . ?
C00B C001 C009 C008 -178.23(17) . . . . ?
C00B C001 B00Q N002 56.2(3) . . . . ?
C00B C001 B00Q C006 -54.0(3) . . . . ?
C00B C001 B00Q C007 177.67(16) . . . . ?
C00B C00E C00G C00A 0.0 . . . . ?
C00B C00E C00G C00R 178.8(2) . . . . ?
C00E C00B N0 C009 3.0(15) . . . . ?
C00E C00B N0 B00Q -177.9(9) . . . . ?
C00E C00G C00A C009 0.0 . . . . ?
C00G C00A C009 C001 0.0 . . . . ?
C00G C00A C009 N0 1.5(8) . . . . ?
C00G C00A C009 C008 177.8(2) . . . . ?
C00A C009 N0 C00B -3.0(15) . . . . ?
C00A C009 N0 B00Q 177.7(4) . . . . ?
C00A C009 C008 C007 -176.96(19) . . . . ?
C00A C009 C008 C2 -177.68(14) . . . . ?
C00A C009 C008 C00C 3.1(3) . . . . ?
C009 C001 C00B C00E 0.0 . . . . ?
C009 C001 B00Q N002 -120.20(19) . . . . ?
C009 C001 B00Q C006 129.57(17) . . . . ?
C009 C001 B00Q C007 1.2(2) . . . . ?
C009 C008 C00C C00K 179.2(2) . . . . ?
N002 C00N C00O C00I 0.11(18) . . . . ?
C006 C005 C00J C00M 0.0 . . . . ?
C006 C005 C003 N002 0.8(2) . . . . ?
C006 C005 C003 C004 -179.79(14) . . . . ?
C005 C006 C00F C00D 0.0 . . . . ?
C005 C006 B00Q C001 118.13(18) . . . . ?
C005 C006 B00Q N002 0.4(2) . . . . ?
C005 C006 B00Q C007 -124.0(2) . . . . ?
C005 C00J C00M C00D 0.0 . . . . ?
C00J C005 C003 N002 -179.73(17) . . . . ?
C00J C005 C003 C0 -179.83(13) . . . . ?
C00J C005 C003 C004 -0.3(3) . . . . ?
C00J C005 C1 C00F 1.2(16) . . . . ?
C00J C005 C1 B00Q 179.2(5) . . . . ?
C00J C00M C00D C00F 0.0 . . . . ?
C00M C00D C00F C006 0.0 . . . . ?
C00M C00D C00F C1 0.7(10) . . . . ?
C00D C00F C1 C005 -1.2(17) . . . . ?
C00D C00F C1 B00Q -178.3(15) . . . . ?
C00F C006 C005 C00J 0.0 . . . . ?
C00F C006 C005 C003 179.55(17) . . . . ?
C00F C006 B00Q C001 -62.2(3) . . . . ?
C00F C006 B00Q N002 -179.90(16) . . . . ?
C00F C006 B00Q C007 55.7(3) . . . . ?
C007 C008 C00C C00K -0.77(19) . . . . ?
C00P C00I C004 C003 -179.37(19) . . . . ?
B00Q C001 C00B C00E -176.2(2) . . . . ?
B00Q C001 C009 C00A 176.8(2) . . . . ?
B00Q C001 C009 C008 -1.46(18) . . . . ?
B00Q N002 C00N C00O 180.0(2) . . . . ?
B00Q N002 C003 C005 -0.4(3) . . . . ?
B00Q N002 C003 C004 -179.94(16) . . . . ?
B00Q C006 C005 C00J 179.69(19) . . . . ?
B00Q C006 C005 C003 -0.76(17) . . . . ?
B00Q C006 C00F C00D -179.6(2) . . . . ?
B00Q C007 C008 C009 -0.2(3) . . . . ?
B00Q C007 C008 C00C 179.81(16) . . . . ?
B00Q C007 C00H C00L -179.3(2) . . . . ?
B00Q C0 C00N C00O 179.9(2) . . . . ?
B00Q C0 C003 C005 -0.28(18) . . . . ?
B00Q C0 C003 C004 -179.9(2) . . . . ?
B00Q C2 C008 C009 0.94(18) . . . . ?
B00Q C2 C008 C00C -179.73(19) . . . . ?
B00Q C2 C00H C00L 179.7(2) . . . . ?
C00R C00G C00A C009 -178.8(2) . . . . ?
N0 C00B C00E C00G -1.6(8) . . . . ?
N0 C009 C008 C2 -1.1(7) . . . . ?
N0 C009 C008 C00C 179.7(7) . . . . ?
N0 B00Q C0 C00N 57.3(6) . . . . ?
N0 B00Q C0 C003 -122.9(6) . . . . ?
N0 B00Q C1 C005 119.0(11) . . . . ?
N0 B00Q C1 C00F -64(2) . . . . ?
N0 B00Q C2 C008 -0.4(6) . . . . ?
N0 B00Q C2 C00H 179.9(6) . . . . ?
C0 B00Q N0 C00B 58.5(15) . . . . ?
C0 B00Q N0 C009 -122.4(8) . . . . ?
C0 B00Q C1 C005 1.5(12) . . . . ?
C0 B00Q C1 C00F 178(2) . . . . ?
C0 B00Q C2 C008 115.94(18) . . . . ?
C0 B00Q C2 C00H -63.8(3) . . . . ?
C0 C00N C00O C00I 0.0 . . . . ?
C00N N002 B00Q C001 56.8(4) . . . . ?
C00N N002 B00Q C006 179.8(3) . . . . ?
C00N N002 B00Q C007 -53.7(4) . . . . ?
C00N N002 C003 C005 179.7(2) . . . . ?
C00N N002 C003 C004 0.2(4) . . . . ?
C00N C0 C003 C005 179.60(16) . . . . ?
C00N C0 C003 C004 0.0 . . . . ?
C00N C00O C00I C00P 179.37(19) . . . . ?
C00N C00O C00I C004 0.0 . . . . ?
C00O C00I C004 C003 0.0 . . . . ?
C00I C004 C003 N002 -0.11(18) . . . . ?
C00I C004 C003 C005 -179.5(2) . . . . ?
C00I C004 C003 C0 0.0 . . . . ?
C003 N002 B00Q C001 -123.0(2) . . . . ?
C003 N002 B00Q C006 0.0(3) . . . . ?
C003 N002 B00Q C007 126.5(2) . . . . ?
C003 N002 C00N C00O -0.2(4) . . . . ?
C003 C005 C00J C00M -179.5(2) . . . . ?
C003 C005 C1 C00F -179.8(8) . . . . ?
C003 C005 C1 B00Q -1.8(13) . . . . ?
C003 C0 C00N C00O 0.0 . . . . ?
C1 C005 C00J C00M -0.7(9) . . . . ?
C1 C005 C003 C0 1.2(8) . . . . ?
C1 C005 C003 C004 -179.3(8) . . . . ?
C1 B00Q N0 C00B -54.3(17) . . . . ?
C1 B00Q N0 C009 124.9(11) . . . . ?
C1 B00Q C0 C00N 179.4(7) . . . . ?
C1 B00Q C0 C003 -0.8(8) . . . . ?
C1 B00Q C2 C008 -124.6(9) . . . . ?
C1 B00Q C2 C00H 55.7(9) . . . . ?
C2 B00Q N0 C00B -179.3(13) . . . . ?
C2 B00Q N0 C009 -0.2(10) . . . . ?
C2 B00Q C0 C00N -52.9(3) . . . . ?
C2 B00Q C0 C003 126.92(17) . . . . ?
C2 B00Q C1 C005 -126.2(9) . . . . ?
C2 B00Q C1 C00F 51(2) . . . . ?
C2 C008 C00C C00K 0.0 . . . . ?
C008 C009 N0 C00B 180.0(8) . . . . ?
C008 C009 N0 B00Q 0.7(11) . . . . ?
C008 C007 B00Q C001 -0.6(3) . . . . ?
C008 C007 B00Q N002 117.0(2) . . . . ?
C008 C007 B00Q C006 -128.3(2) . . . . ?
C008 C007 C00H C00L -1.5(4) . . . . ?
C008 C2 C00H C00L 0.0 . . . . ?
C008 C00C C00K C00L 0.0 . . . . ?
C008 C00C C00K C3 172.9(11) . . . . ?
C00C C00K C00L C00H 0.0 . . . . ?
C00K C00L C00H C007 0.8(2) . . . . ?
C00K C00L C00H C2 0.0 . . . . ?
C00H C007 B00Q C001 177.3(3) . . . . ?
C00H C007 B00Q N002 -65.1(4) . . . . ?
C00H C007 B00Q C006 49.7(4) . . . . ?
C00H C007 C008 C009 -178.5(2) . . . . ?
C00H C007 C008 C00C 1.5(4) . . . . ?
C00H C2 C008 C009 -179.33(17) . . . . ?
C00H C2 C008 C00C 0.0 . . . . ?
C3 C00K C00L C00H -173.0(11) . . . . ?

_olex2_exptl_crystal_mounting_method cryoroop
_olex2_submission_special_instructions 'No special instructions were received'
