# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
# 
#######################################################################

data_yang01
_database_code_depnum_ccdc_archive 'CCDC 2099085'
loop_
_audit_author_name
_audit_author_address
'huanan huang'
;Jiujiang University
China
;
_audit_update_record             
;
2021-07-25 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-02-03
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H33 B N4'
_chemical_formula_sum            'C36 H33 B N4'
_chemical_formula_weight         532.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.3480(15)
_cell_length_b                   9.7155(7)
_cell_length_c                   20.1083(19)
_cell_angle_alpha                90
_cell_angle_beta                 95.494(9)
_cell_angle_gamma                90
_cell_volume                     2790.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2236
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.8490
_cell_measurement_theta_min      3.9720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4941
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         3.626
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  21.00   1.00   10.00    --  -40.73  38.00  30.00   83
  2  ω     43.00  95.00   1.00   10.00    --   40.73-125.00  60.00   52
  3  ω     30.00 108.00   1.00   15.00    --  107.58 -94.00  60.00   78
  4  ω     37.00 131.00   1.00   15.00    --  107.58 -45.00  30.00   94
  5  ω     79.00 178.00   1.00   15.00    --  107.58  30.00  60.00   99
  6  ω    107.00 134.00   1.00   15.00    --  107.58 125.00 -60.00   27
  7  ω     41.00 133.00   1.00   15.00    --  107.58 -45.00-120.00   92
  8  ω     43.00  96.00   1.00   15.00    --  107.58 -94.00 -90.00   53
  9  ω   -112.00 -12.00   1.00   10.00    --  -40.73 -77.00-120.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0373403000
_diffrn_orient_matrix_UB_12      0.0233574000
_diffrn_orient_matrix_UB_13      -0.0735416000
_diffrn_orient_matrix_UB_21      0.0932925000
_diffrn_orient_matrix_UB_22      -0.0530727000
_diffrn_orient_matrix_UB_23      -0.0224534000
_diffrn_orient_matrix_UB_31      -0.0393564000
_diffrn_orient_matrix_UB_32      -0.1474757000
_diffrn_orient_matrix_UB_33      -0.0035266000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3513
_reflns_number_total             4941
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         4941
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1400
_refine_ls_R_factor_gt           0.1150
_refine_ls_restrained_S_all      1.058
_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)+(0.1087P)²+11.1146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3236
_refine_ls_wR_factor_ref         0.3393
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.654(7)
 0.346(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C25(H25), C26(H26),
  C30(H30), C31(H31), C33(H33), C34(H34)
3.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C35(H35A,H35B,H35C), C36(H36A,H36B,
 H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.4215(3) 0.1791(5) 0.7021(3) 0.0371(11) Uani 1 1 d . . . . .
H1 H 0.400646 0.183007 0.740758 0.045 Uiso 1 1 calc R U . . .
N2 N 0.7989(4) 0.3077(6) 0.6806(3) 0.0403(12) Uani 1 1 d . . . . .
N3 N 1.0719(4) 0.1645(6) 0.8913(3) 0.0592(18) Uani 1 1 d . . . . .
N004 N 0.8846(5) 0.4880(6) 0.4273(3) 0.0534(15) Uani 1 1 d . . . . .
C1 C 0.2021(4) 0.0529(6) 0.5939(3) 0.0374(14) Uani 1 1 d . . . . .
C2 C 0.1099(5) 0.0049(7) 0.6003(4) 0.0459(16) Uani 1 1 d . . . . .
H2 H 0.071536 -0.018065 0.561992 0.055 Uiso 1 1 calc R U . . .
C3 C 0.0760(5) -0.0086(7) 0.6607(4) 0.0500(17) Uani 1 1 d . . . . .
H3 H 0.015169 -0.039963 0.662852 0.060 Uiso 1 1 calc R U . . .
C4 C 0.1312(5) 0.0240(8) 0.7202(4) 0.0559(19) Uani 1 1 d . . . . .
H4 H 0.108649 0.012352 0.761635 0.067 Uiso 1 1 calc R U . . .
C5 C 0.2202(5) 0.0740(8) 0.7147(4) 0.0507(17) Uani 1 1 d . . . . .
H5 H 0.256645 0.098609 0.753604 0.061 Uiso 1 1 calc R U . . .
C6 C 0.2587(4) 0.0896(6) 0.6532(3) 0.0388(14) Uani 1 1 d . . . . .
C7 C 0.2394(4) 0.0697(6) 0.5277(3) 0.0344(13) Uani 1 1 d . . . . .
C8 C 0.1791(5) 0.0420(7) 0.4684(3) 0.0468(16) Uani 1 1 d . . . . .
H8 H 0.117387 0.016258 0.471930 0.056 Uiso 1 1 calc R U . . .
C9 C 0.2107(5) 0.0525(7) 0.4064(3) 0.0490(17) Uani 1 1 d . . . . .
H9 H 0.170086 0.032979 0.368735 0.059 Uiso 1 1 calc R U . . .
C10 C 0.3007(4) 0.0913(7) 0.3989(3) 0.0432(15) Uani 1 1 d . . . . .
H10 H 0.321383 0.097245 0.356505 0.052 Uiso 1 1 calc R U . . .
C11 C 0.3610(4) 0.1217(6) 0.4552(3) 0.0398(14) Uani 1 1 d . . . . .
H11 H 0.422005 0.149238 0.450274 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3310(4) 0.1114(6) 0.5193(3) 0.0330(13) Uani 1 1 d . . . . .
C13 C 0.3958(4) 0.1442(6) 0.5788(3) 0.0315(12) Uani 1 1 d . . . . .
C14 C 0.4887(4) 0.1774(6) 0.5762(3) 0.0333(13) Uani 1 1 d . . . . .
H14 H 0.512634 0.178405 0.534852 0.040 Uiso 1 1 calc R U . . .
C15 C 0.5495(4) 0.2103(6) 0.6340(3) 0.0319(12) Uani 1 1 d . . . . .
C16 C 0.6446(4) 0.2411(6) 0.6294(3) 0.0370(13) Uani 1 1 d . . . . .
H16 H 0.667409 0.240771 0.587584 0.044 Uiso 1 1 calc R U . . .
C17 C 0.7053(4) 0.2720(6) 0.6853(3) 0.0369(13) Uani 1 1 d . . . . .
C18 C 0.6684(4) 0.2688(6) 0.7481(3) 0.0377(14) Uani 1 1 d . . . . .
H18 H 0.707964 0.287030 0.786532 0.045 Uiso 1 1 calc R U . . .
C19 C 0.5767(4) 0.2397(6) 0.7539(3) 0.0358(13) Uani 1 1 d . . . . .
H19 H 0.554791 0.238429 0.795969 0.043 Uiso 1 1 calc R U . . .
C20 C 0.5150(4) 0.2117(5) 0.6975(3) 0.0329(13) Uani 1 1 d . . . . .
C21 C 0.8691(4) 0.2668(6) 0.7323(3) 0.0349(13) Uani 1 1 d . . . . .
C22 C 0.9438(4) 0.3557(6) 0.7516(3) 0.0389(14) Uani 1 1 d . . . . .
H22 H 0.948155 0.439525 0.729776 0.047 Uiso 1 1 calc R U . . .
C23 C 1.0107(4) 0.3208(6) 0.8024(3) 0.0420(15) Uani 1 1 d . . . . .
H23 H 1.060383 0.380685 0.813336 0.050 Uiso 1 1 calc R U . . .
C24 C 1.0063(4) 0.1987(6) 0.8378(3) 0.0380(14) Uani 1 1 d . . . . .
C25 C 0.9327(4) 0.1071(6) 0.8171(3) 0.0363(13) Uani 1 1 d . . . . .
H25 H 0.928566 0.022939 0.838684 0.044 Uiso 1 1 calc R U . . .
C26 C 0.8672(4) 0.1414(6) 0.7655(3) 0.0350(13) Uani 1 1 d . . . . .
H26 H 0.820078 0.078675 0.752284 0.042 Uiso 1 1 calc R U . . .
C27 C 1.0686(6) 0.0358(9) 0.9231(4) 0.067(2) Uani 1 1 d . . . . .
H27A H 1.012716 0.029906 0.945655 0.101 Uiso 1 1 calc R U . . .
H27B H 1.122416 0.025694 0.954891 0.101 Uiso 1 1 calc R U . . .
H27C H 1.068320 -0.036104 0.890284 0.101 Uiso 1 1 calc R U . . .
C28 C 1.1552(5) 0.2474(8) 0.9031(4) 0.060(2) Uani 1 1 d . . . . .
H28A H 1.189918 0.243657 0.864606 0.090 Uiso 1 1 calc R U . . .
H28B H 1.193130 0.212838 0.941318 0.090 Uiso 1 1 calc R U . . .
H28C H 1.137875 0.341016 0.911039 0.090 Uiso 1 1 calc R U . . .
C29 C 0.8276(4) 0.3570(6) 0.6185(3) 0.0366(14) Uani 1 1 d . . . . .
C30 C 0.8915(4) 0.2893(6) 0.5847(3) 0.0390(14) Uani 1 1 d . . . . .
H30 H 0.921711 0.212516 0.604069 0.047 Uiso 1 1 calc R U . . .
C31 C 0.9128(5) 0.3324(6) 0.5215(3) 0.0434(15) Uani 1 1 d . . . . .
H31 H 0.956500 0.283843 0.499443 0.052 Uiso 1 1 calc R U . . .
C32 C 0.8687(5) 0.4483(7) 0.4914(3) 0.0421(15) Uani 1 1 d . . . . .
C33 C 0.8069(4) 0.5219(6) 0.5284(3) 0.0416(15) Uani 1 1 d . . . . .
H33 H 0.779010 0.601854 0.510508 0.050 Uiso 1 1 calc R U . . .
C34 C 0.7867(4) 0.4774(6) 0.5910(3) 0.0400(14) Uani 1 1 d . . . . .
H34 H 0.745928 0.527865 0.614801 0.048 Uiso 1 1 calc R U . . .
C35 C 0.8439(6) 0.6100(8) 0.3988(4) 0.066(2) Uani 1 1 d . . . . .
H35A H 0.777309 0.598709 0.391217 0.100 Uiso 1 1 calc R U . . .
H35B H 0.869045 0.628361 0.357143 0.100 Uiso 1 1 calc R U . . .
H35C H 0.857958 0.685685 0.428834 0.100 Uiso 1 1 calc R U . . .
C36 C 0.9424(5) 0.4068(7) 0.3899(3) 0.0534(18) Uani 1 1 d . . . . .
H36A H 1.002393 0.394948 0.414818 0.080 Uiso 1 1 calc R U . . .
H36B H 0.950380 0.451893 0.348366 0.080 Uiso 1 1 calc R U . . .
H36C H 0.913829 0.318519 0.381245 0.080 Uiso 1 1 calc R U . . .
B1 B 0.3590(5) 0.1401(7) 0.6469(4) 0.0358(15) 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 H1 0.8600 . ?
N1 C20 1.389(7) . ?
N1 B1 1.411(9) . ?
N2 C17 1.399(8) . ?
N2 C21 1.432(7) . ?
N2 C29 1.435(8) . ?
N3 C24 1.400(8) . ?
N3 C27 1.407(9) . ?
N3 C28 1.442(8) . ?
N004 C32 1.385(8) . ?
N004 C35 1.417(9) . ?
N004 C36 1.412(9) . ?
C1 C2 1.420(9) . ?
C1 C6 1.422(9) . ?
C1 C7 1.491(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.357(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.411(9) . ?
C6 B1 1.537(9) . ?
C7 C8 1.430(9) . ?
C7 C12 1.401(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.369(10) . ?
C9 H9 0.9300 . ?
C9 C10 1.368(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.400(8) . ?
C12 C13 1.479(8) . ?
C13 C14 1.377(8) . ?
C13 B1 1.515(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.421(8) . ?
C15 C16 1.409(8) . ?
C15 C20 1.414(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(8) . ?
C17 C18 1.415(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.363(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(8) . ?
C21 C22 1.402(8) . ?
C21 C26 1.391(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(9) . ?
C23 H23 0.9300 . ?
C23 C24 1.387(9) . ?
C24 C25 1.413(8) . ?
C25 H25 0.9300 . ?
C25 C26 1.373(8) . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.362(9) . ?
C29 C34 1.398(9) . ?
C30 H30 0.9300 . ?
C30 C31 1.398(9) . ?
C31 H31 0.9300 . ?
C31 C32 1.401(9) . ?
C32 C33 1.406(9) . ?
C33 H33 0.9300 . ?
C33 C34 1.389(9) . ?
C34 H34 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

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
C20 N1 H1 118.2 . . ?
C20 N1 B1 123.7(5) . . ?
B1 N1 H1 118.2 . . ?
C17 N2 C21 119.7(5) . . ?
C17 N2 C29 120.0(5) . . ?
C21 N2 C29 119.0(5) . . ?
C24 N3 C27 120.7(6) . . ?
C24 N3 C28 118.6(6) . . ?
C27 N3 C28 119.1(6) . . ?
C32 N004 C35 120.7(6) . . ?
C32 N004 C36 119.8(6) . . ?
C36 N004 C35 119.5(6) . . ?
C2 C1 C6 117.9(6) . . ?
C2 C1 C7 122.3(6) . . ?
C6 C1 C7 119.7(5) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 C1 122.0(7) . . ?
C3 C2 H2 119.0 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(6) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.5(7) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 H5 118.3 . . ?
C4 C5 C6 123.4(7) . . ?
C6 C5 H5 118.3 . . ?
C1 C6 B1 118.4(6) . . ?
C5 C6 C1 117.9(6) . . ?
C5 C6 B1 123.6(6) . . ?
C8 C7 C1 119.0(5) . . ?
C12 C7 C1 124.1(5) . . ?
C12 C7 C8 117.0(6) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.2(6) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(6) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(6) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.9(6) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C13 119.3(5) . . ?
C11 C12 C7 120.4(5) . . ?
C11 C12 C13 120.4(5) . . ?
C12 C13 B1 118.7(5) . . ?
C14 C13 C12 123.7(5) . . ?
C14 C13 B1 117.6(5) . . ?
C13 C14 H14 118.6 . . ?
C13 C14 C15 122.8(5) . . ?
C15 C14 H14 118.6 . . ?
C16 C15 C14 121.1(5) . . ?
C16 C15 C20 118.9(5) . . ?
C20 C15 C14 120.0(5) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 C15 121.9(6) . . ?
C17 C16 H16 119.1 . . ?
N2 C17 C18 120.6(5) . . ?
C16 C17 N2 122.0(6) . . ?
C16 C17 C18 117.4(6) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 C17 121.8(6) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 120.9(6) . . ?
C20 C19 H19 119.5 . . ?
N1 C20 C15 118.8(5) . . ?
N1 C20 C19 122.1(5) . . ?
C19 C20 C15 119.1(5) . . ?
C22 C21 N2 119.7(5) . . ?
C26 C21 N2 123.1(5) . . ?
C26 C21 C22 117.1(5) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 121.0(6) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 119.0 . . ?
C22 C23 C24 121.9(6) . . ?
C24 C23 H23 119.0 . . ?
N3 C24 C25 120.3(5) . . ?
C23 C24 N3 122.5(6) . . ?
C23 C24 C25 117.2(5) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.5(6) . . ?
C26 C25 H25 119.7 . . ?
C21 C26 H26 118.9 . . ?
C25 C26 C21 122.2(5) . . ?
C25 C26 H26 118.9 . . ?
N3 C27 H27A 109.5 . . ?
N3 C27 H27B 109.5 . . ?
N3 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N3 C28 H28A 109.5 . . ?
N3 C28 H28B 109.5 . . ?
N3 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 N2 122.4(6) . . ?
C30 C29 C34 118.9(6) . . ?
C34 C29 N2 118.6(6) . . ?
C29 C30 H30 119.2 . . ?
C29 C30 C31 121.7(6) . . ?
C31 C30 H30 119.2 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.3(6) . . ?
C32 C31 H31 119.9 . . ?
N004 C32 C31 121.3(6) . . ?
N004 C32 C33 121.2(6) . . ?
C31 C32 C33 117.5(6) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 C32 121.2(6) . . ?
C34 C33 H33 119.4 . . ?
C29 C34 H34 119.9 . . ?
C33 C34 C29 120.2(6) . . ?
C33 C34 H34 119.9 . . ?
N004 C35 H35A 109.5 . . ?
N004 C35 H35B 109.5 . . ?
N004 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N004 C36 H36A 109.5 . . ?
N004 C36 H36B 109.5 . . ?
N004 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N1 B1 C6 123.5(6) . . ?
N1 B1 C13 116.9(6) . . ?
C13 B1 C6 119.5(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C17 C18 C19 177.4(6) . . . . ?
N2 C21 C22 C23 178.2(6) . . . . ?
N2 C21 C26 C25 -176.7(6) . . . . ?
N2 C29 C30 C31 174.5(6) . . . . ?
N2 C29 C34 C33 -174.6(5) . . . . ?
N3 C24 C25 C26 178.8(6) . . . . ?
N004 C32 C33 C34 176.1(6) . . . . ?
C1 C2 C3 C4 -0.3(11) . . . . ?
C1 C6 B1 N1 -179.9(6) . . . . ?
C1 C6 B1 C13 -2.3(8) . . . . ?
C1 C7 C8 C9 -178.3(6) . . . . ?
C1 C7 C12 C11 178.6(5) . . . . ?
C1 C7 C12 C13 -1.3(9) . . . . ?
C2 C1 C6 C5 1.0(9) . . . . ?
C2 C1 C6 B1 179.3(6) . . . . ?
C2 C1 C7 C8 2.6(9) . . . . ?
C2 C1 C7 C12 -177.3(6) . . . . ?
C2 C3 C4 C5 1.8(11) . . . . ?
C3 C4 C5 C6 -2.0(11) . . . . ?
C4 C5 C6 C1 0.6(10) . . . . ?
C4 C5 C6 B1 -177.6(7) . . . . ?
C5 C6 B1 N1 -1.7(10) . . . . ?
C5 C6 B1 C13 175.9(6) . . . . ?
C6 C1 C2 C3 -1.1(10) . . . . ?
C6 C1 C7 C8 -175.4(6) . . . . ?
C6 C1 C7 C12 4.7(9) . . . . ?
C7 C1 C2 C3 -179.2(6) . . . . ?
C7 C1 C6 C5 179.1(6) . . . . ?
C7 C1 C6 B1 -2.6(8) . . . . ?
C7 C8 C9 C10 -0.6(11) . . . . ?
C7 C12 C13 C14 175.7(5) . . . . ?
C7 C12 C13 B1 -3.7(8) . . . . ?
C8 C7 C12 C11 -1.3(9) . . . . ?
C8 C7 C12 C13 178.8(5) . . . . ?
C8 C9 C10 C11 -0.6(11) . . . . ?
C9 C10 C11 C12 0.8(10) . . . . ?
C10 C11 C12 C7 0.2(9) . . . . ?
C10 C11 C12 C13 -179.9(6) . . . . ?
C11 C12 C13 C14 -4.2(9) . . . . ?
C11 C12 C13 B1 176.4(5) . . . . ?
C12 C7 C8 C9 1.6(10) . . . . ?
C12 C13 C14 C15 179.2(5) . . . . ?
C12 C13 B1 N1 -176.7(5) . . . . ?
C12 C13 B1 C6 5.5(8) . . . . ?
C13 C14 C15 C16 178.7(6) . . . . ?
C13 C14 C15 C20 -0.9(9) . . . . ?
C14 C13 B1 N1 3.9(8) . . . . ?
C14 C13 B1 C6 -173.9(5) . . . . ?
C14 C15 C16 C17 -179.3(6) . . . . ?
C14 C15 C20 N1 0.7(8) . . . . ?
C14 C15 C20 C19 177.8(5) . . . . ?
C15 C16 C17 N2 -177.6(6) . . . . ?
C15 C16 C17 C18 1.3(9) . . . . ?
C16 C15 C20 N1 -179.0(5) . . . . ?
C16 C15 C20 C19 -1.8(8) . . . . ?
C16 C17 C18 C19 -1.5(9) . . . . ?
C17 N2 C21 C22 -142.9(6) . . . . ?
C17 N2 C21 C26 36.8(9) . . . . ?
C17 N2 C29 C30 -118.0(7) . . . . ?
C17 N2 C29 C34 60.5(8) . . . . ?
C17 C18 C19 C20 0.0(9) . . . . ?
C18 C19 C20 N1 178.7(5) . . . . ?
C18 C19 C20 C15 1.7(9) . . . . ?
C20 N1 B1 C6 173.4(5) . . . . ?
C20 N1 B1 C13 -4.3(8) . . . . ?
C20 C15 C16 C17 0.4(9) . . . . ?
C21 N2 C17 C16 -145.7(6) . . . . ?
C21 N2 C17 C18 35.5(9) . . . . ?
C21 N2 C29 C30 48.3(8) . . . . ?
C21 N2 C29 C34 -133.2(6) . . . . ?
C21 C22 C23 C24 -1.7(10) . . . . ?
C22 C21 C26 C25 3.0(9) . . . . ?
C22 C23 C24 N3 -177.4(7) . . . . ?
C22 C23 C24 C25 3.5(10) . . . . ?
C23 C24 C25 C26 -2.1(9) . . . . ?
C24 C25 C26 C21 -1.1(9) . . . . ?
C26 C21 C22 C23 -1.6(9) . . . . ?
C27 N3 C24 C23 -175.7(8) . . . . ?
C27 N3 C24 C25 3.4(11) . . . . ?
C28 N3 C24 C23 -10.5(11) . . . . ?
C28 N3 C24 C25 168.6(7) . . . . ?
C29 N2 C17 C16 20.5(9) . . . . ?
C29 N2 C17 C18 -158.3(6) . . . . ?
C29 N2 C21 C22 50.8(8) . . . . ?
C29 N2 C21 C26 -129.5(6) . . . . ?
C29 C30 C31 C32 0.4(10) . . . . ?
C30 C29 C34 C33 4.0(9) . . . . ?
C30 C31 C32 N004 -176.1(6) . . . . ?
C30 C31 C32 C33 3.2(9) . . . . ?
C31 C32 C33 C34 -3.2(10) . . . . ?
C32 C33 C34 C29 -0.4(9) . . . . ?
C34 C29 C30 C31 -4.0(9) . . . . ?
C35 N004 C32 C31 -176.2(7) . . . . ?
C35 N004 C32 C33 4.5(11) . . . . ?
C36 N004 C32 C31 3.3(10) . . . . ?
C36 N004 C32 C33 -176.0(7) . . . . ?
B1 N1 C20 C15 2.1(8) . . . . ?
B1 N1 C20 C19 -175.0(6) . . . . ?
B1 C13 C14 C15 -1.4(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.644
_oxdiff_exptl_absorpt_empirical_full_min 0.434
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.654(7)
2 0.346(7)

####################################################################### 
# 
# 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_yang02-0219
_database_code_depnum_ccdc_archive 'CCDC 2099086'
loop_
_audit_author_name
_audit_author_address
'huanan huang'
;Jiujiang University
China
;
_audit_update_record             
;
2021-07-25 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-02-19
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6270)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H23 B N2'
_chemical_formula_sum            'C32 H23 B N2'
_chemical_formula_weight         446.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   8.1281(4)
_cell_length_b                   14.6359(10)
_cell_length_c                   22.9977(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.688(5)
_cell_angle_gamma                90
_cell_volume                     2730.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.5890
_cell_measurement_theta_min      2.9990
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.480
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.086
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10196
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.596
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_min         3.582
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      4.00  82.00   1.00    1.00    --   40.73 -99.00 120.00   78
  2  ω     56.00 140.00   1.00    2.00    --  107.58 -77.00  30.00   84
  3  ω     55.00  88.00   1.00    1.00    --   40.73-125.00 -90.00   33
  4  ω     26.00  98.00   1.00    2.00    --  107.58 -94.00 -60.00   72
  5  ω    118.00 174.00   1.00    2.00    --  107.58  45.00  90.00   56
  6  ω    115.00 154.00   1.00    2.00    --  107.58 125.00  90.00   39
  7  ω    148.00 178.00   1.00    2.00    --  107.58 125.00 120.00   30
  8  ω    104.00 146.00   1.00    2.00    --  107.58 104.00  27.00   42
  9  ω     85.00 116.00   1.00    2.00    --  107.58  45.00  90.00   31
 10  ω     78.00 178.00   1.00    2.00    --  107.58  61.00-180.00  100
 11  ω   -120.00  -5.00   1.00    1.00    --  -40.73 -19.00-120.00  115
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0805241000
_diffrn_orient_matrix_UB_12      0.0937709000
_diffrn_orient_matrix_UB_13      -0.0127970000
_diffrn_orient_matrix_UB_21      -0.0882054000
_diffrn_orient_matrix_UB_22      -0.0387605000
_diffrn_orient_matrix_UB_23      -0.0559269000
_diffrn_orient_matrix_UB_31      -0.1478153000
_diffrn_orient_matrix_UB_32      -0.0278774000
_diffrn_orient_matrix_UB_33      0.0348134000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3888
_reflns_number_total             4826
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.0011(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   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4826
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0933
_refine_ls_restrained_S_all      1.016
_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)+(0.1321P)²+2.7093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2568
_refine_ls_wR_factor_ref         0.2696
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid bond restraints
 C5, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C4 \\sim C5: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
  C14(H14), C17(H17), C18(H18), C20(H20), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
;
_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 0.3184(4) 0.2101(3) 0.70104(16) 0.0664(10) Uani 1 1 d . . . . .
N1 N 0.9325(3) 0.52803(19) 0.59225(12) 0.0533(7) Uani 1 1 d . . . . .
B1 B 0.5761(6) 0.1456(3) 0.65585(17) 0.0679(11) Uani 1 1 d . . . . .
N2 N 0.7231(4) 0.1668(2) 0.63002(13) 0.0707(9) Uani 1 1 d . . . . .
H2 H 0.783356 0.122316 0.619300 0.085 Uiso 1 1 calc R U . . .
C2 C 0.2183(5) 0.2779(3) 0.7191(2) 0.0897(15) Uani 1 1 d . . . . .
H2A H 0.251588 0.338108 0.714474 0.108 Uiso 1 1 calc R U . . .
C3 C 0.0719(5) 0.2626(4) 0.7436(3) 0.112(2) Uani 1 1 d . . . . .
H3 H 0.009893 0.312283 0.754830 0.134 Uiso 1 1 calc R U . . .
C4 C 0.0158(6) 0.1783(4) 0.7519(2) 0.0997(13) Uani 1 1 d . U . . .
H4 H -0.084014 0.168545 0.768536 0.120 Uiso 1 1 calc R U . . .
C5 C 0.1113(5) 0.1056(4) 0.7348(2) 0.0959(13) Uani 1 1 d . U . . .
H5 H 0.073211 0.046495 0.740123 0.115 Uiso 1 1 calc R U . . .
C6 C 0.2611(5) 0.1176(3) 0.71010(17) 0.0766(12) Uani 1 1 d . . . . .
C7 C 0.3626(6) 0.0375(3) 0.69408(16) 0.0785(12) Uani 1 1 d . . . . .
C8 C 0.5123(6) 0.0458(3) 0.66747(15) 0.0733(11) Uani 1 1 d . . . . .
C9 C 0.6078(9) -0.0304(3) 0.65404(19) 0.1037(18) Uani 1 1 d . . . . .
H9 H 0.707087 -0.022904 0.636662 0.124 Uiso 1 1 calc R U . . .
C10 C 0.5503(10) -0.1187(3) 0.6674(2) 0.116(2) Uani 1 1 d . . . . .
H10 H 0.610859 -0.170333 0.658832 0.139 Uiso 1 1 calc R U . . .
C11 C 0.4037(10) -0.1265(4) 0.6932(2) 0.124(2) Uani 1 1 d . . . . .
H11 H 0.365378 -0.184388 0.702217 0.148 Uiso 1 1 calc R U . . .
C12 C 0.3124(8) -0.0518(3) 0.7061(2) 0.1036(18) Uani 1 1 d . . . . .
H12 H 0.213256 -0.060494 0.723397 0.124 Uiso 1 1 calc R U . . .
C13 C 0.4716(4) 0.2251(2) 0.67413(15) 0.0620(9) Uani 1 1 d . . . . .
C14 C 0.5297(4) 0.3118(2) 0.66408(15) 0.0586(8) Uani 1 1 d . . . . .
H14 H 0.468034 0.361773 0.674971 0.070 Uiso 1 1 calc R U . . .
C15 C 0.6816(4) 0.3277(2) 0.63750(13) 0.0556(8) Uani 1 1 d . . . . .
C16 C 0.7773(5) 0.2555(3) 0.62070(14) 0.0614(9) Uani 1 1 d . . . . .
C17 C 0.9231(5) 0.2731(3) 0.59517(16) 0.0715(10) Uani 1 1 d . . . . .
H17 H 0.988606 0.224789 0.584153 0.086 Uiso 1 1 calc R U . . .
C18 C 0.9726(4) 0.3621(3) 0.58585(15) 0.0630(9) Uani 1 1 d . . . . .
H18 H 1.070445 0.372520 0.568091 0.076 Uiso 1 1 calc R U . . .
C19 C 0.8799(4) 0.4360(2) 0.60231(13) 0.0533(8) Uani 1 1 d . . . . .
C20 C 0.7358(4) 0.4201(2) 0.62898(14) 0.0545(8) Uani 1 1 d . . . . .
H20 H 0.673671 0.468888 0.641431 0.065 Uiso 1 1 calc R U . . .
C21 C 0.8259(3) 0.5886(2) 0.56033(13) 0.0507(7) Uani 1 1 d . . . . .
C22 C 0.8205(4) 0.6818(3) 0.57329(15) 0.0591(8) Uani 1 1 d . . . . .
H22 H 0.885590 0.704768 0.604670 0.071 Uiso 1 1 calc R U . . .
C23 C 0.7188(4) 0.7406(3) 0.53982(17) 0.0687(10) Uani 1 1 d . . . . .
H23 H 0.717671 0.802700 0.548363 0.082 Uiso 1 1 calc R U . . .
C24 C 0.6190(4) 0.7062(3) 0.49353(17) 0.0694(10) Uani 1 1 d . . . . .
H24 H 0.552646 0.745458 0.470464 0.083 Uiso 1 1 calc R U . . .
C25 C 0.6188(4) 0.6143(3) 0.48205(15) 0.0654(10) Uani 1 1 d . . . . .
H25 H 0.549298 0.591189 0.451875 0.078 Uiso 1 1 calc R U . . .
C26 C 0.7205(4) 0.5558(3) 0.51472(14) 0.0566(8) Uani 1 1 d . . . . .
H26 H 0.718815 0.493628 0.506255 0.068 Uiso 1 1 calc R U . . .
C27 C 1.0925(3) 0.5551(2) 0.61386(12) 0.0458(7) Uani 1 1 d . . . . .
C28 C 1.1829(4) 0.6200(2) 0.58576(14) 0.0537(8) Uani 1 1 d . . . . .
H28 H 1.138607 0.647004 0.551655 0.064 Uiso 1 1 calc R U . . .
C29 C 1.3395(4) 0.6449(2) 0.60827(18) 0.0624(9) Uani 1 1 d . . . . .
H29 H 1.399876 0.687935 0.588876 0.075 Uiso 1 1 calc R U . . .
C30 C 1.4056(4) 0.6061(3) 0.65904(18) 0.0674(10) Uani 1 1 d . . . . .
H30 H 1.508500 0.624540 0.674819 0.081 Uiso 1 1 calc R U . . .
C31 C 1.3192(4) 0.5406(3) 0.68604(16) 0.0643(9) Uani 1 1 d . . . . .
H31 H 1.365419 0.512406 0.719464 0.077 Uiso 1 1 calc R U . . .
C32 C 1.1628(4) 0.5154(2) 0.66410(14) 0.0548(8) Uani 1 1 d . . . . .
H32 H 1.104511 0.471350 0.683388 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.365(6) . ?
C1 C6 1.452(5) . ?
C1 C13 1.443(5) . ?
N1 C19 1.437(4) . ?
N1 C21 1.412(4) . ?
N1 C27 1.419(4) . ?
B1 N2 1.403(6) . ?
B1 C8 1.579(6) . ?
B1 C13 1.515(6) . ?
N2 H2 0.8600 . ?
N2 C16 1.392(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.368(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.333(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.388(6) . ?
C6 C7 1.492(7) . ?
C7 C8 1.403(6) . ?
C7 C12 1.403(6) . ?
C8 C9 1.404(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.415(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.365(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.431(5) . ?
C15 C16 1.382(5) . ?
C15 C20 1.439(5) . ?
C16 C17 1.380(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(5) . ?
C19 C20 1.376(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.398(5) . ?
C21 C26 1.396(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.391(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.390(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.371(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.379(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.385(4) . ?
C27 C32 1.384(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.392(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.376(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.362(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.386(5) . ?
C32 H32 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 C1 C6 115.6(4) . . ?
C2 C1 C13 124.6(3) . . ?
C13 C1 C6 119.8(4) . . ?
C21 N1 C19 119.6(2) . . ?
C21 N1 C27 121.7(3) . . ?
C27 N1 C19 118.8(2) . . ?
N2 B1 C8 125.0(4) . . ?
N2 B1 C13 117.1(3) . . ?
C13 B1 C8 117.9(4) . . ?
B1 N2 H2 118.1 . . ?
C16 N2 B1 123.9(4) . . ?
C16 N2 H2 118.1 . . ?
C1 C2 H2A 118.0 . . ?
C1 C2 C3 124.0(5) . . ?
C3 C2 H2A 118.0 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.6(6) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.8(5) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 H5 118.6 . . ?
C4 C5 C6 122.7(5) . . ?
C6 C5 H5 118.6 . . ?
C1 C6 C7 120.7(4) . . ?
C5 C6 C1 118.3(5) . . ?
C5 C6 C7 121.0(4) . . ?
C8 C7 C6 123.3(3) . . ?
C12 C7 C6 120.7(5) . . ?
C12 C7 C8 116.0(5) . . ?
C7 C8 B1 117.2(4) . . ?
C7 C8 C9 122.3(4) . . ?
C9 C8 B1 120.4(4) . . ?
C8 C9 H9 120.6 . . ?
C8 C9 C10 118.9(6) . . ?
C10 C9 H9 120.6 . . ?
C9 C10 H10 120.7 . . ?
C11 C10 C9 118.6(6) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 119.1 . . ?
C12 C11 C10 121.8(5) . . ?
C12 C11 H11 119.1 . . ?
C7 C12 H12 118.8 . . ?
C11 C12 C7 122.4(6) . . ?
C11 C12 H12 118.8 . . ?
C1 C13 B1 121.1(3) . . ?
C14 C13 C1 121.8(4) . . ?
C14 C13 B1 117.1(3) . . ?
C13 C14 H14 118.8 . . ?
C13 C14 C15 122.4(3) . . ?
C15 C14 H14 118.8 . . ?
C14 C15 C20 119.4(3) . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 C20 119.9(3) . . ?
C15 C16 N2 118.8(3) . . ?
C17 C16 N2 121.9(4) . . ?
C17 C16 C15 119.4(3) . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.5(4) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C18 C19 N1 121.0(3) . . ?
C20 C19 N1 120.0(3) . . ?
C20 C19 C18 118.9(3) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 C15 119.7(3) . . ?
C19 C20 H20 120.2 . . ?
C22 C21 N1 121.9(3) . . ?
C26 C21 N1 120.1(3) . . ?
C26 C21 C22 118.0(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.8(4) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.7(3) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.8(3) . . ?
C26 C25 H25 119.6 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.8(3) . . ?
C25 C26 H26 119.6 . . ?
C28 C27 N1 122.0(3) . . ?
C28 C27 C32 118.3(3) . . ?
C32 C27 N1 119.7(3) . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.4(3) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.4(3) . . ?
C30 C29 H29 119.8 . . ?
C29 C30 H30 120.2 . . ?
C31 C30 C29 119.5(3) . . ?
C31 C30 H30 120.2 . . ?
C30 C31 H31 119.7 . . ?
C30 C31 C32 120.6(3) . . ?
C32 C31 H31 119.7 . . ?
C27 C32 C31 120.8(3) . . ?
C27 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?

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 0.2(9) . . . . ?
C1 C6 C7 C8 -2.9(5) . . . . ?
C1 C6 C7 C12 176.1(4) . . . . ?
C1 C13 C14 C15 179.9(3) . . . . ?
N1 C19 C20 C15 178.4(3) . . . . ?
N1 C21 C22 C23 177.6(3) . . . . ?
N1 C21 C26 C25 -178.2(3) . . . . ?
N1 C27 C28 C29 180.0(3) . . . . ?
N1 C27 C32 C31 179.8(3) . . . . ?
B1 N2 C16 C15 -0.2(5) . . . . ?
B1 N2 C16 C17 179.9(3) . . . . ?
B1 C8 C9 C10 177.2(4) . . . . ?
B1 C13 C14 C15 0.1(5) . . . . ?
N2 B1 C8 C7 179.7(3) . . . . ?
N2 B1 C8 C9 2.8(6) . . . . ?
N2 B1 C13 C1 180.0(3) . . . . ?
N2 B1 C13 C14 -0.2(5) . . . . ?
N2 C16 C17 C18 179.2(3) . . . . ?
C2 C1 C6 C5 1.2(5) . . . . ?
C2 C1 C6 C7 -177.9(4) . . . . ?
C2 C1 C13 B1 179.4(4) . . . . ?
C2 C1 C13 C14 -0.3(6) . . . . ?
C2 C3 C4 C5 0.1(8) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C4 C5 C6 C1 -1.0(6) . . . . ?
C4 C5 C6 C7 178.0(4) . . . . ?
C5 C6 C7 C8 178.0(4) . . . . ?
C5 C6 C7 C12 -2.9(6) . . . . ?
C6 C1 C2 C3 -0.8(7) . . . . ?
C6 C1 C13 B1 -1.0(5) . . . . ?
C6 C1 C13 C14 179.3(3) . . . . ?
C6 C7 C8 B1 1.6(5) . . . . ?
C6 C7 C8 C9 178.4(4) . . . . ?
C6 C7 C12 C11 -178.5(4) . . . . ?
C7 C8 C9 C10 0.5(6) . . . . ?
C8 B1 N2 C16 -179.4(3) . . . . ?
C8 B1 C13 C1 -0.3(5) . . . . ?
C8 B1 C13 C14 179.5(3) . . . . ?
C8 C7 C12 C11 0.6(7) . . . . ?
C8 C9 C10 C11 -0.3(7) . . . . ?
C9 C10 C11 C12 0.2(8) . . . . ?
C10 C11 C12 C7 -0.4(8) . . . . ?
C12 C7 C8 B1 -177.5(3) . . . . ?
C12 C7 C8 C9 -0.6(6) . . . . ?
C13 C1 C2 C3 178.8(4) . . . . ?
C13 C1 C6 C5 -178.4(3) . . . . ?
C13 C1 C6 C7 2.5(5) . . . . ?
C13 B1 N2 C16 0.3(5) . . . . ?
C13 B1 C8 C7 0.0(5) . . . . ?
C13 B1 C8 C9 -176.9(3) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C13 C14 C15 C20 -179.3(3) . . . . ?
C14 C15 C16 N2 0.1(5) . . . . ?
C14 C15 C16 C17 180.0(3) . . . . ?
C14 C15 C20 C19 -178.6(3) . . . . ?
C15 C16 C17 C18 -0.7(5) . . . . ?
C16 C15 C20 C19 2.2(4) . . . . ?
C16 C17 C18 C19 0.9(6) . . . . ?
C17 C18 C19 N1 -179.9(3) . . . . ?
C17 C18 C19 C20 0.5(5) . . . . ?
C18 C19 C20 C15 -2.0(4) . . . . ?
C19 N1 C21 C22 145.2(3) . . . . ?
C19 N1 C21 C26 -34.1(4) . . . . ?
C19 N1 C27 C28 148.6(3) . . . . ?
C19 N1 C27 C32 -30.6(4) . . . . ?
C20 C15 C16 N2 179.3(3) . . . . ?
C20 C15 C16 C17 -0.8(5) . . . . ?
C21 N1 C19 C18 124.3(3) . . . . ?
C21 N1 C19 C20 -56.0(4) . . . . ?
C21 N1 C27 C28 -30.1(4) . . . . ?
C21 N1 C27 C32 150.7(3) . . . . ?
C21 C22 C23 C24 1.2(5) . . . . ?
C22 C21 C26 C25 2.5(5) . . . . ?
C22 C23 C24 C25 1.4(6) . . . . ?
C23 C24 C25 C26 -2.1(5) . . . . ?
C24 C25 C26 C21 0.1(5) . . . . ?
C26 C21 C22 C23 -3.1(5) . . . . ?
C27 N1 C19 C18 -54.4(4) . . . . ?
C27 N1 C19 C20 125.2(3) . . . . ?
C27 N1 C21 C22 -36.1(4) . . . . ?
C27 N1 C21 C26 144.6(3) . . . . ?
C27 C28 C29 C30 -0.7(5) . . . . ?
C28 C27 C32 C31 0.6(5) . . . . ?
C28 C29 C30 C31 2.5(5) . . . . ?
C29 C30 C31 C32 -2.7(5) . . . . ?
C30 C31 C32 C27 1.1(5) . . . . ?
C32 C27 C28 C29 -0.8(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.641 0.000 0.500 286.3 85.8 ?
2 -0.733 0.500 0.000 286.3 85.8 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.907
_oxdiff_exptl_absorpt_empirical_full_min 0.401
