# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_202314-cjx-8cl_auto
_database_code_depnum_ccdc_archive 'CCDC 2365379'
loop_
_audit_author_name
_audit_author_address
'chi jingxian' 'Henan Normal University '
_audit_update_record             
;
2024-12-25 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-12-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H13 B3 Cl N'
_chemical_formula_sum            'C9 H13 B3 Cl N'
_chemical_formula_weight         203.08
_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'
Cl Cl 0.3639 0.7018 '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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   8.6443(4)
_cell_length_b                   6.7370(3)
_cell_length_c                   10.0988(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.990(5)
_cell_angle_gamma                90
_cell_volume                     549.09(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1286
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.6760
_cell_measurement_theta_min      4.6800
_shelx_estimated_absorpt_T_max   0.775
_shelx_estimated_absorpt_T_min   0.775
_exptl_absorpt_coefficient_mu    2.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2202
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.288
_diffrn_reflns_theta_min         4.690
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  10.00   1.00    1.00    --  -35.62  37.00  92.00   65
  2  ω    -69.00 -29.00   1.00    1.00    --  -35.62 -37.00 -63.00   40
  3  ω   -104.00 -70.00   1.00    1.00    --  -35.62 -37.00 -63.00   34
  4  ω     36.00  61.00   1.00    1.00    --   35.62  37.00  92.00   25
  5  ω     39.00 126.00   1.00    2.04    --  106.81 -37.00 -63.00   87
  6  ω    100.00 173.00   1.00    2.04    --  106.81  37.00  92.00   73
  7  ω    -31.00  44.00   1.00    1.00    --   35.62 -57.00-180.00   75
  8  ω      1.00  26.00   1.00    1.00    --   35.62 -37.00 -63.00   25
  9  ω     36.00 102.00   1.00    1.00    --   35.62  57.00 -90.00   66
 10  ω     49.00  76.00   1.00    2.04    --  106.81 -95.00  90.00   27
 11  ω     77.00 122.00   1.00    2.04    --  106.81 -45.00-150.00   45
 12  ω     50.00 100.00   1.00    2.04    --  106.81 -95.00 -30.00   50
 13  ω    115.00 142.00   1.00    2.04    --  106.81 178.00 -30.00   27
 14  ω     80.00 107.00   1.00    2.04    --  106.81 178.00 -30.00   27
 15  ω    113.00 140.00   1.00    2.04    --  106.81  77.00   0.00   27
 16  ω     79.00 104.00   1.00    2.04    --  106.81 -95.00  90.00   25
 17  ω     41.00 109.00   1.00    2.04    --  106.81 -30.00 150.00   68
 18  ω     40.00 104.00   1.00    2.04    --  106.81-111.00 -60.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1012
_reflns_number_total             1140
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.079
_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)+(0.0844P)²+0.1538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1452
_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:
 C4(H4), C5(H5), C6(H6), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Cl1 Cl 0.83628(8) 0.750000 0.51023(8) 0.0656(3) Uani 1 2 d S T P . .
N8 N 0.3430(3) 0.750000 0.1813(2) 0.0393(5) Uani 1 2 d S T P . .
C1 C 0.4875(3) 0.750000 0.2878(3) 0.0392(6) Uani 1 2 d S T P . .
H1 H 0.574(4) 0.750000 0.265(3) 0.041(8) Uiso 1 2 d S . P . .
C2 C 0.5008(3) 0.750000 0.4302(2) 0.0392(6) Uani 1 2 d S T P . .
C3 C 0.6550(3) 0.750000 0.5452(3) 0.0447(6) Uani 1 2 d S T P . .
C4 C 0.6611(4) 0.750000 0.6823(3) 0.0532(7) Uani 1 2 d S T P . .
H4 H 0.762979 0.750000 0.756560 0.064 Uiso 1 2 calc R U P . .
C5 C 0.5146(4) 0.750000 0.7111(3) 0.0563(8) Uani 1 2 d S T P . .
H5 H 0.520035 0.750000 0.804699 0.068 Uiso 1 2 calc R U P . .
C6 C 0.3641(4) 0.750000 0.6040(3) 0.0533(7) Uani 1 2 d S T P . .
H6 H 0.267781 0.750000 0.625116 0.064 Uiso 1 2 calc R U P . .
C7 C 0.3534(3) 0.750000 0.4614(3) 0.0427(6) Uani 1 2 d S T P . .
C8 C 0.2021(3) 0.750000 0.3447(3) 0.0484(7) Uani 1 2 d S T P . .
H8 H 0.102712 0.750000 0.360874 0.058 Uiso 1 2 calc R U P . .
C9 C 0.1993(3) 0.750000 0.2105(3) 0.0455(6) Uani 1 2 d S T P . .
H9 H 0.102(5) 0.750000 0.129(4) 0.058(9) Uiso 1 2 d S . P . .
B1 B 0.1841(6) 0.8801(10) -0.1027(4) 0.114(2) Uani 1 1 d . . . . .
H1A H 0.139(5) 0.977(8) -0.045(4) 0.137(14) Uiso 1 1 d . . . . .
H1B H 0.190(5) 0.925(6) -0.196(4) 0.125(13) Uiso 1 1 d . . . . .
H1C H 0.080(10) 0.750000 -0.124(7) 0.15(3) Uiso 1 2 d S . P . .
B2 B 0.3427(4) 0.750000 0.0238(3) 0.0503(8) Uani 1 2 d S T P . .
H2 H 0.442(5) 0.825(7) 0.023(4) 0.137(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C3 1.725(3) . ?
N8 C1 1.325(3) . ?
N8 C9 1.375(3) . ?
N8 B2 1.590(3) . ?
C1 H1 0.86(3) . ?
C1 C2 1.401(3) . ?
C2 C3 1.421(4) . ?
C2 C7 1.417(4) . ?
C3 C4 1.366(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.362(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.411(4) . ?
C7 C8 1.412(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.347(4) . ?
C9 H9 0.94(4) . ?
B1 B1 1.753(14) 4_575 ?
B1 H1A 1.04(5) . ?
B1 H1B 1.01(4) . ?
B1 H1C 1.22(6) . ?
B1 B2 1.739(4) . ?
B2 H2 1.00(4) . ?
B2 H2 1.00(4) 4_575 ?

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
C1 N8 C9 119.2(2) . . ?
C1 N8 B2 118.4(2) . . ?
C9 N8 B2 122.4(2) . . ?
N8 C1 H1 116.5(19) . . ?
N8 C1 C2 122.7(2) . . ?
C2 C1 H1 120.8(19) . . ?
C1 C2 C3 123.2(2) . . ?
C1 C2 C7 118.6(2) . . ?
C7 C2 C3 118.2(2) . . ?
C2 C3 Cl1 119.2(2) . . ?
C4 C3 Cl1 120.0(2) . . ?
C4 C3 C2 120.9(3) . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 119.5(3) . . ?
C6 C7 C8 123.6(3) . . ?
C8 C7 C2 116.9(2) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 H8 119.5 . . ?
N8 C9 H9 114(2) . . ?
C8 C9 N8 121.6(2) . . ?
C8 C9 H9 124(2) . . ?
B1 B1 H1A 129(3) 4_575 . ?
B1 B1 H1B 108(2) 4_575 . ?
B1 B1 H1C 44(3) 4_575 . ?
H1A B1 H1B 119(4) . . ?
H1A B1 H1C 99(4) . . ?
H1B B1 H1C 110(4) . . ?
B2 B1 B1 59.7(3) . 4_575 ?
B2 B1 H1A 105(2) . . ?
B2 B1 H1B 123(2) . . ?
B2 B1 H1C 96(3) . . ?
N8 B2 B1 116.9(2) . 4_575 ?
N8 B2 B1 116.9(2) . . ?
N8 B2 H2 109(2) . . ?
N8 B2 H2 109(2) . 4_575 ?
B1 B2 B1 60.5(5) . 4_575 ?
B1 B2 H2 101(2) . . ?
B1 B2 H2 134(2) 4_575 . ?
B1 B2 H2 101(2) 4_575 4_575 ?
B1 B2 H2 134(2) . 4_575 ?
H2 B2 H2 60(5) . 4_575 ?

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
Cl1 C3 C4 C5 180.000(1) . . . . ?
N8 C1 C2 C3 180.000(1) . . . . ?
N8 C1 C2 C7 0.000(1) . . . . ?
C1 N8 C9 C8 0.000(0) . . . . ?
C1 N8 B2 B1 -145.6(3) . . . . ?
C1 N8 B2 B1 145.6(3) . . . 4_575 ?
C1 C2 C3 Cl1 0.000(1) . . . . ?
C1 C2 C3 C4 180.000(1) . . . . ?
C1 C2 C7 C6 180.000(1) . . . . ?
C1 C2 C7 C8 0.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C2 C7 C8 C9 0.000(1) . . . . ?
C3 C2 C7 C6 0.000(1) . . . . ?
C3 C2 C7 C8 180.000(1) . . . . ?
C3 C4 C5 C6 0.000(2) . . . . ?
C4 C5 C6 C7 0.000(1) . . . . ?
C5 C6 C7 C2 0.000(1) . . . . ?
C5 C6 C7 C8 180.000(1) . . . . ?
C6 C7 C8 C9 180.000(1) . . . . ?
C7 C2 C3 Cl1 180.000(0) . . . . ?
C7 C2 C3 C4 0.000(1) . . . . ?
C7 C8 C9 N8 0.000(1) . . . . ?
C9 N8 C1 C2 0.000(1) . . . . ?
C9 N8 B2 B1 -34.4(3) . . . 4_575 ?
C9 N8 B2 B1 34.4(3) . . . . ?
B1 B1 B2 N8 -107.2(2) 4_575 . . . ?
B2 N8 C1 C2 180.000(0) . . . . ?
B2 N8 C9 C8 180.000(0) . . . . ?

_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
;
####################################################################### 
# 
# 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_20241125-cjx_auto
_database_code_depnum_ccdc_archive 'CCDC 2405543'
loop_
_audit_author_name
_audit_author_address
'chi jingxian' 'Henan Normal University '
_audit_update_record             
;
2024-12-25 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-12-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H20 B3 N O2'
_chemical_formula_sum            'C6 H20 B3 N O2'
_chemical_formula_weight         170.66
_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'
O O 0.0492 0.0322 '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                   8.6344(9)
_cell_length_b                   18.1239(16)
_cell_length_c                   7.5131(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.852(9)
_cell_angle_gamma                90
_cell_volume                     1175.10(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1837
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5420
_cell_measurement_theta_min      5.0850
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.139a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.965
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.014
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4533
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.293
_diffrn_reflns_theta_min         4.880
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00 -46.00   1.00    1.27    --  -35.37 -23.00  -2.00   33
  2  ω    -33.00   3.00   1.00    1.27    --  -35.37  23.00 162.00   36
  3  ω      9.00  35.00   1.00    1.27    --  -35.37  23.00 162.00   26
  4  ω    -61.00 -36.00   1.00    1.27    --  -35.37  23.00 162.00   25
  5  ω     81.00 108.00   1.00    5.06    --  106.81 -23.00  -2.00   27
  6  ω     92.00 152.00   1.00    5.06    --  106.81  23.00 162.00   60
  7  ω   -102.00 -19.00   1.00    1.27    --  -35.37 -57.00-180.00   83
  8  ω     63.00 107.00   1.00    1.27    --   35.37 178.00-150.00   44
  9  ω    -11.00  14.00   1.00    1.27    --   35.37 -23.00  -2.00   25
 10  ω     34.00  59.00   1.00    1.27    --   35.37  23.00 162.00   25
 11  ω     77.00 108.00   1.00    1.27    --   35.37-178.00 -30.00   31
 12  ω     61.00 108.00   1.00    1.27    --   35.37-178.00 -60.00   47
 13  ω     67.00  93.00   1.00    1.27    --   35.37 178.00   0.00   26
 14  ω     51.00 125.00   1.00    5.06    --  106.81 -61.00  60.00   74
 15  ω     42.00 122.00   1.00    5.06    --  106.81 -45.00 -30.00   80
 16  ω     44.00 124.00   1.00    5.06    --  106.81 -61.00 150.00   80
 17  ω     41.00 104.00   1.00    5.06    --  106.81-111.00 -60.00   63
 18  ω     85.00 134.00   1.00    5.06    --  106.81  30.00  30.00   49
 19  ω     50.00  75.00   1.00    5.06    --  106.81-111.00  90.00   25
 20  ω     73.00  98.00   1.00    5.06    --  106.81 -94.00 150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1580
_reflns_number_total             2207
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.139a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.139a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.139a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0822
_refine_ls_restrained_S_all      1.053
_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)+(0.1709P)²+0.0214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2398
_refine_ls_wR_factor_ref         0.2685
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.2731(2) 0.26111(11) 0.8392(2) 0.0738(6) Uani 1 1 d . . . . .
O2 O 0.3515(2) 0.36257(9) 0.6955(2) 0.0609(5) Uani 1 1 d . . . . .
N1 N 0.1053(2) 0.36535(12) 0.4732(3) 0.0563(6) Uani 1 1 d . . . . .
H1A H 0.171(4) 0.3438(17) 0.403(4) 0.060(7) Uiso 1 1 d . . . . .
H1B H 0.149(4) 0.4112(18) 0.503(4) 0.076(9) Uiso 1 1 d . . . . .
C1 C 0.0978(3) 0.32170(14) 0.6377(3) 0.0597(6) Uani 1 1 d . . . . .
H1C H 0.054521 0.273670 0.608330 0.072 Uiso 1 1 calc R U . . .
H1D H 0.027446 0.345923 0.717058 0.072 Uiso 1 1 calc R U . . .
C2 C 0.2514(3) 0.31066(13) 0.7357(3) 0.0572(6) Uani 1 1 d . . . . .
C3 C 0.5057(3) 0.36913(14) 0.7907(4) 0.0645(7) Uani 1 1 d . . . . .
C4 C 0.6023(4) 0.30125(18) 0.7534(4) 0.0814(9) Uani 1 1 d . . . . .
H4A H 0.556464 0.258910 0.807565 0.122 Uiso 1 1 calc R U . . .
H4B H 0.705508 0.308138 0.801825 0.122 Uiso 1 1 calc R U . . .
H4C H 0.605954 0.293752 0.627078 0.122 Uiso 1 1 calc R U . . .
C5 C 0.4816(4) 0.3817(2) 0.9859(4) 0.0823(9) Uani 1 1 d . . . . .
H5A H 0.405105 0.419484 1.000111 0.123 Uiso 1 1 calc R U . . .
H5B H 0.577499 0.396788 1.042969 0.123 Uiso 1 1 calc R U . . .
H5C H 0.446749 0.336742 1.039211 0.123 Uiso 1 1 calc R U . . .
C6 C 0.5725(4) 0.43715(19) 0.7052(5) 0.0891(10) Uani 1 1 d . . . . .
H6A H 0.588279 0.427657 0.581412 0.134 Uiso 1 1 calc R U . . .
H6B H 0.669729 0.449321 0.763475 0.134 Uiso 1 1 calc R U . . .
H6C H 0.501782 0.477635 0.716518 0.134 Uiso 1 1 calc R U . . .
B1 B -0.0567(3) 0.37156(17) 0.3643(4) 0.0635(7) Uani 1 1 d . . . . .
H1E H -0.095(5) 0.315(2) 0.326(5) 0.108(12) Uiso 1 1 d . . . . .
H1F H -0.129(4) 0.395(2) 0.455(5) 0.091(10) Uiso 1 1 d . . . . .
B2 B -0.0799(6) 0.4600(2) 0.2507(5) 0.0918(12) Uani 1 1 d . . . . .
H2A H -0.005(5) 0.497(2) 0.317(6) 0.105(12) Uiso 1 1 d . . . . .
H2B H -0.207(7) 0.480(4) 0.231(9) 0.18(2) Uiso 1 1 d . . . . .
H2C H -0.033(4) 0.449(2) 0.092(5) 0.098(11) Uiso 1 1 d . . . . .
B3 B -0.0262(5) 0.3845(2) 0.1283(4) 0.0800(10) Uani 1 1 d . . . . .
H3A H -0.125(5) 0.360(2) 0.039(5) 0.103(12) Uiso 1 1 d . . . . .
H3B H 0.094(6) 0.370(2) 0.126(7) 0.122(15) Uiso 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 C2 1.199(3) . ?
O2 C2 1.319(3) . ?
O2 C3 1.496(3) . ?
N1 H1A 0.88(3) . ?
N1 H1B 0.94(3) . ?
N1 C1 1.471(3) . ?
N1 B1 1.601(3) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C1 C2 1.509(3) . ?
C3 C4 1.517(4) . ?
C3 C5 1.506(4) . ?
C3 C6 1.513(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
B1 H1E 1.11(4) . ?
B1 H1F 1.03(4) . ?
B1 B2 1.824(5) . ?
B1 B3 1.817(5) . ?
B2 H2A 1.05(4) . ?
B2 H2B 1.17(6) . ?
B2 H2C 1.29(4) . ?
B2 B3 1.722(6) . ?
B3 H2C 1.20(4) . ?
B3 H3A 1.16(4) . ?
B3 H3B 1.07(5) . ?

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 O2 C3 121.80(18) . . ?
H1A N1 H1B 106(3) . . ?
C1 N1 H1A 108.2(19) . . ?
C1 N1 H1B 108(2) . . ?
C1 N1 B1 113.94(19) . . ?
B1 N1 H1A 107.2(19) . . ?
B1 N1 H1B 113(2) . . ?
N1 C1 H1C 108.6 . . ?
N1 C1 H1D 108.6 . . ?
N1 C1 C2 114.81(19) . . ?
H1C C1 H1D 107.5 . . ?
C2 C1 H1C 108.6 . . ?
C2 C1 H1D 108.6 . . ?
O1 C2 O2 126.4(2) . . ?
O1 C2 C1 122.1(2) . . ?
O2 C2 C1 111.45(19) . . ?
O2 C3 C4 109.5(2) . . ?
O2 C3 C5 109.2(2) . . ?
O2 C3 C6 102.0(2) . . ?
C5 C3 C4 113.4(3) . . ?
C5 C3 C6 110.9(3) . . ?
C6 C3 C4 111.3(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 B1 H1E 108(2) . . ?
N1 B1 H1F 103(2) . . ?
N1 B1 B2 112.4(2) . . ?
N1 B1 B3 110.8(2) . . ?
H1E B1 H1F 112(3) . . ?
B2 B1 H1E 131(2) . . ?
B2 B1 H1F 84(2) . . ?
B3 B1 H1E 85(2) . . ?
B3 B1 H1F 135(2) . . ?
B3 B1 B2 56.4(2) . . ?
B1 B2 H2A 107(2) . . ?
B1 B2 H2B 115(3) . . ?
B1 B2 H2C 105.3(17) . . ?
H2A B2 H2B 115(4) . . ?
H2A B2 H2C 110(3) . . ?
H2B B2 H2C 104(3) . . ?
B3 B2 B1 61.6(2) . . ?
B3 B2 H2A 126(2) . . ?
B3 B2 H2B 117(3) . . ?
B3 B2 H2C 44.2(16) . . ?
B1 B3 H2C 109.8(19) . . ?
B1 B3 H3A 112.5(19) . . ?
B1 B3 H3B 99(3) . . ?
B2 B3 B1 62.0(2) . . ?
B2 B3 H2C 48.3(19) . . ?
B2 B3 H3A 114(2) . . ?
B2 B3 H3B 119(3) . . ?
H2C B3 H3A 102(3) . . ?
H2C B3 H3B 106(3) . . ?
H3A B3 H3B 126(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O1 -158.5(2) . . . . ?
N1 C1 C2 O2 23.2(3) . . . . ?
N1 B1 B2 B3 100.8(3) . . . . ?
N1 B1 B3 B2 -103.7(3) . . . . ?
C1 N1 B1 B2 146.4(2) . . . . ?
C1 N1 B1 B3 -152.4(2) . . . . ?
C2 O2 C3 C4 64.6(3) . . . . ?
C2 O2 C3 C5 -60.0(3) . . . . ?
C2 O2 C3 C6 -177.4(2) . . . . ?
C3 O2 C2 O1 -5.5(4) . . . . ?
C3 O2 C2 C1 172.75(19) . . . . ?
B1 N1 C1 C2 175.9(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
;
####################################################################### 
# 
# 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_20231213-cjx_auto
_database_code_depnum_ccdc_archive 'CCDC 2365394'
loop_
_audit_author_name
_audit_author_address
'chi jingxian' 'Henan Normal University '
_audit_update_record             
;
2024-12-25 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-12-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H16 B3 N'
_chemical_formula_sum            'C11 H16 B3 N'
_chemical_formula_weight         194.68
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9433(4)
_cell_length_b                   9.1729(3)
_cell_length_c                   15.5599(5)
_cell_angle_alpha                100.947(3)
_cell_angle_beta                 106.184(4)
_cell_angle_gamma                96.479(3)
_cell_volume                     1184.83(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4489
_cell_measurement_temperature    298
_cell_measurement_theta_max      71.2990
_cell_measurement_theta_min      5.1690
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8764
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.314
_diffrn_reflns_theta_min         4.988
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -77.00   1.00    1.00    --  -35.62-162.00 -69.00   25
  2  ω    -65.00 -40.00   1.00    1.00    --  -35.62 117.00 168.00   25
  3  ω    -92.00 -67.00   1.00    1.00    --  -35.62 162.00 -41.00   25
  4  ω     23.00  82.00   1.00    1.00    --   35.62-117.00  81.00   59
  5  ω     80.00 105.00   1.00    1.00    --   35.62-162.00 -69.00   25
  6  ω     40.00 110.00   1.00    1.00    --  106.81-117.00  81.00   70
  7  ω    100.00 137.00   1.00    1.00    --  106.81-162.00 -69.00   37
  8  ω    103.00 129.00   1.00    1.00    --  106.81 117.00 168.00   26
  9  ω     95.00 127.00   1.00    1.00    --  106.81 162.00 -41.00   32
 10  ω   -107.00 -81.00   1.00    1.00    --  -35.62-178.00   0.00   26
 11  ω   -105.00 -53.00   1.00    1.00    --  -35.62 -38.00  60.00   52
 12  ω    -74.00 -19.00   1.00    1.00    --  -35.62 -38.00 -30.00   55
 13  ω    -78.00 -39.00   1.00    1.00    --  -35.62-178.00   0.00   39
 14  ω     30.00 103.00   1.00    1.00    --   35.62  38.00 -30.00   73
 15  ω    -33.00  39.00   1.00    1.00    --   35.62 -38.00 150.00   72
 16  ω     81.00 107.00   1.00    1.00    --   35.62 178.00  60.00   26
 17  ω    -21.00  62.00   1.00    1.00    --   35.62 -77.00-120.00   83
 18  ω    117.00 175.00   1.00    1.00    --  106.81  45.00-150.00   58
 19  ω     77.00 108.00   1.00    1.00    --  106.81-111.00 -60.00   31
 20  ω     89.00 141.00   1.00    1.00    --  106.81 178.00  90.00   52
 21  ω     41.00  85.00   1.00    1.00    --  106.81-111.00 -90.00   44
 22  ω    109.00 173.00   1.00    1.00    --  106.81  77.00 150.00   64
 23  ω    109.00 135.00   1.00    1.00    --  106.81  77.00  90.00   26
 24  ω     89.00 171.00   1.00    1.00    --  106.81  61.00-120.00   82
 25  ω     51.00  77.00   1.00    1.00    --  106.81 -30.00  90.00   26
 26  ω     37.00 104.00   1.00    1.00    --  106.81 -95.00  90.00   67
 27  ω    148.00 173.00   1.00    1.00    --  106.81 111.00 -60.00   25
 28  ω    111.00 155.00   1.00    1.00    --  106.81 111.00  30.00   44
 29  ω    145.00 174.00   1.00    1.00    --  106.81  77.00  90.00   29
 30  ω     50.00 124.00   1.00    1.00    --  106.81 -45.00  60.00   74
 31  ω     85.00 126.00   1.00    1.00    --  106.81 -30.00  90.00   41
 32  ω    114.00 174.00   1.00    1.00    --  106.81 111.00  60.00   60
 33  ω     51.00  76.00   1.00    1.00    --  106.81-111.00  30.00   25
 34  ω     96.00 174.00   1.00    1.00    --  106.81  45.00 120.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3907
_reflns_number_total             4485
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4485
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.047
_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)+(0.0552P)²+0.1546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1204
_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:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C13(H13), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21),
  C22(H22)
;
_atom_sites_solution_hydrogens   mixed
_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 0.76344(13) 0.70155(12) 0.37599(7) 0.0459(3) Uani 1 1 d . . . . .
C1 C 0.60695(16) 0.65360(15) 0.33646(9) 0.0528(3) Uani 1 1 d . . . . .
H1 H 0.569812 0.605685 0.274321 0.063 Uiso 1 1 calc R U . . .
C2 C 0.50014(16) 0.67254(15) 0.38410(9) 0.0518(3) Uani 1 1 d . . . . .
H2 H 0.392947 0.636959 0.354246 0.062 Uiso 1 1 calc R U . . .
C3 C 0.55143(15) 0.74497(13) 0.47720(9) 0.0432(3) Uani 1 1 d . . . . .
C4 C 0.71318(16) 0.79773(16) 0.51644(9) 0.0503(3) Uani 1 1 d . . . . .
H4 H 0.753074 0.849795 0.577776 0.060 Uiso 1 1 calc R U . . .
C5 C 0.81397(16) 0.77336(16) 0.46515(9) 0.0516(3) Uani 1 1 d . . . . .
H5 H 0.921766 0.808012 0.493302 0.062 Uiso 1 1 calc R U . . .
C6 C 0.44142(15) 0.76635(14) 0.53213(9) 0.0450(3) Uani 1 1 d . . . . .
C7 C 0.31512(17) 0.65330(17) 0.52066(11) 0.0585(4) Uani 1 1 d . . . . .
H7 H 0.296951 0.563790 0.476584 0.070 Uiso 1 1 calc R U . . .
C8 C 0.21639(19) 0.6740(2) 0.57490(13) 0.0695(5) Uani 1 1 d . . . . .
H8 H 0.134146 0.596933 0.568352 0.083 Uiso 1 1 calc R U . . .
C9 C 0.23914(19) 0.8082(2) 0.63857(12) 0.0694(5) Uani 1 1 d . . . . .
H9 H 0.171494 0.822032 0.674097 0.083 Uiso 1 1 calc R U . . .
C10 C 0.3621(2) 0.9212(2) 0.64924(11) 0.0652(4) Uani 1 1 d . . . . .
H10 H 0.376855 1.012221 0.691513 0.078 Uiso 1 1 calc R U . . .
C11 C 0.46385(17) 0.90009(16) 0.59734(9) 0.0531(3) Uani 1 1 d . . . . .
H11 H 0.548371 0.976227 0.606117 0.064 Uiso 1 1 calc R U . . .
B1 B 0.8721(3) 0.7736(3) 0.23165(14) 0.0713(5) Uani 1 1 d . . . . .
H1A H 0.894(2) 0.7130(19) 0.1672(12) 0.080(5) Uiso 1 1 d . . . . .
H1B H 0.756(2) 0.808(2) 0.2238(13) 0.100(6) Uiso 1 1 d . . . . .
H1C H 0.973(2) 0.885(2) 0.2656(14) 0.103(7) Uiso 1 1 d . . . . .
B2 B 0.8850(2) 0.66677(19) 0.32038(12) 0.0534(4) Uani 1 1 d . . . . .
H2A H 0.992(2) 0.6410(19) 0.3675(12) 0.083(5) Uiso 1 1 d . . . . .
H2B H 0.831(2) 0.565(2) 0.2675(12) 0.088(6) Uiso 1 1 d . . . . .
B3 B 1.0285(3) 0.8303(3) 0.32942(15) 0.0744(6) Uani 1 1 d . . . . .
H3A H 1.146(2) 0.809(2) 0.3246(13) 0.090(6) Uiso 1 1 d . . . . .
H3B H 1.032(2) 0.914(2) 0.3922(13) 0.090(6) Uiso 1 1 d . . . . .
N2 N 0.72282(12) 0.82135(11) 0.86598(7) 0.0424(2) Uani 1 1 d . . . . .
C12 C 0.57668(15) 0.74129(15) 0.82311(9) 0.0473(3) Uani 1 1 d . . . . .
H12 H 0.544955 0.706654 0.759495 0.057 Uiso 1 1 calc R U . . .
C13 C 0.47266(15) 0.70884(15) 0.86979(9) 0.0483(3) Uani 1 1 d . . . . .
H13 H 0.372366 0.653272 0.837558 0.058 Uiso 1 1 calc R U . . .
C14 C 0.51585(14) 0.75835(13) 0.96504(8) 0.0411(3) Uani 1 1 d . . . . .
C15 C 0.66507(15) 0.84635(15) 1.00784(9) 0.0482(3) Uani 1 1 d . . . . .
H15 H 0.698196 0.885987 1.071056 0.058 Uiso 1 1 calc R U . . .
C16 C 0.76348(16) 0.87486(15) 0.95717(9) 0.0493(3) Uani 1 1 d . . . . .
H16 H 0.862770 0.933894 0.987393 0.059 Uiso 1 1 calc R U . . .
C17 C 0.41087(14) 0.71842(14) 1.01865(9) 0.0433(3) Uani 1 1 d . . . . .
C18 C 0.31365(16) 0.57804(16) 0.99161(11) 0.0546(3) Uani 1 1 d . . . . .
H18 H 0.313449 0.509806 0.939063 0.066 Uiso 1 1 calc R U . . .
C19 C 0.21717(18) 0.53908(18) 1.04229(13) 0.0664(4) Uani 1 1 d . . . . .
H19 H 0.153699 0.444238 1.024255 0.080 Uiso 1 1 calc R U . . .
C20 C 0.21469(19) 0.6400(2) 1.11924(12) 0.0683(5) Uani 1 1 d . . . . .
H20 H 0.148391 0.613920 1.152600 0.082 Uiso 1 1 calc R U . . .
C21 C 0.31035(19) 0.77974(19) 1.14698(11) 0.0638(4) Uani 1 1 d . . . . .
H21 H 0.308861 0.847964 1.199106 0.077 Uiso 1 1 calc R U . . .
C22 C 0.40867(17) 0.81839(16) 1.09713(10) 0.0524(3) Uani 1 1 d . . . . .
H22 H 0.473963 0.912389 1.116438 0.063 Uiso 1 1 calc R U . . .
B4 B 0.8856(2) 0.6810(2) 0.74842(13) 0.0594(4) Uani 1 1 d . . . . .
H4A H 0.9111(18) 0.6834(17) 0.6819(11) 0.064(4) Uiso 1 1 d . . . . .
H4B H 0.7845(19) 0.5938(18) 0.7419(11) 0.072(5) Uiso 1 1 d . . . . .
H4C H 1.005(2) 0.6491(19) 0.7991(11) 0.074(5) Uiso 1 1 d . . . . .
B5 B 0.84231(19) 0.85468(18) 0.81026(11) 0.0480(3) Uani 1 1 d . . . . .
H5A H 0.9171(18) 0.9653(17) 0.8468(10) 0.063(4) Uiso 1 1 d . . . . .
H5B H 0.7723(19) 0.8684(18) 0.7420(11) 0.070(5) Uiso 1 1 d . . . . .
B6 B 1.0252(2) 0.7797(2) 0.84873(13) 0.0602(4) Uani 1 1 d . . . . .
H6A H 1.030(2) 0.7676(18) 0.9198(11) 0.075(5) Uiso 1 1 d . . . . .
H6B H 1.134(2) 0.8448(18) 0.8433(11) 0.072(5) Uiso 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 C1 1.3450(17) . ?
N1 C5 1.3413(16) . ?
N1 B2 1.5907(18) . ?
C1 H1 0.9300 . ?
C1 C2 1.3694(18) . ?
C2 H2 0.9300 . ?
C2 C3 1.3949(18) . ?
C3 C4 1.3918(18) . ?
C3 C6 1.4784(17) . ?
C4 H4 0.9300 . ?
C4 C5 1.3704(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.3915(19) . ?
C6 C11 1.3903(19) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.3813(19) . ?
C11 H11 0.9300 . ?
B1 H1A 1.131(17) . ?
B1 H1B 1.10(2) . ?
B1 H1C 1.21(2) . ?
B1 B2 1.825(3) . ?
B1 B3 1.700(3) . ?
B2 H2A 1.111(18) . ?
B2 H2B 1.078(18) . ?
B2 B3 1.817(3) . ?
B3 H1C 1.21(2) . ?
B3 H3A 1.105(19) . ?
B3 H3B 1.114(19) . ?
N2 C12 1.3431(16) . ?
N2 C16 1.3394(16) . ?
N2 B5 1.5907(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.3703(17) . ?
C13 H13 0.9300 . ?
C13 C14 1.3920(17) . ?
C14 C15 1.3905(17) . ?
C14 C17 1.4788(16) . ?
C15 H15 0.9300 . ?
C15 C16 1.3703(17) . ?
C16 H16 0.9300 . ?
C17 C18 1.3888(18) . ?
C17 C22 1.3873(18) . ?
C18 H18 0.9300 . ?
C18 C19 1.3823(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.375(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.378(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.3837(19) . ?
C22 H22 0.9300 . ?
B4 H4A 1.125(15) . ?
B4 H4B 1.106(16) . ?
B4 H4C 1.241(17) . ?
B4 B5 1.838(2) . ?
B4 B6 1.714(3) . ?
B5 H5A 1.102(15) . ?
B5 H5B 1.110(16) . ?
B5 B6 1.836(2) . ?
B6 H4C 1.260(17) . ?
B6 H6A 1.121(16) . ?
B6 H6B 1.118(16) . ?

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
C1 N1 B2 121.13(11) . . ?
C5 N1 C1 117.66(11) . . ?
C5 N1 B2 121.13(11) . . ?
N1 C1 H1 118.7 . . ?
N1 C1 C2 122.59(12) . . ?
C2 C1 H1 118.7 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.29(12) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C6 122.47(12) . . ?
C4 C3 C2 116.42(12) . . ?
C4 C3 C6 121.11(12) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.34(12) . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 122.66(12) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C7 C6 C3 121.04(12) . . ?
C11 C6 C3 120.26(12) . . ?
C11 C6 C7 118.70(13) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.03(15) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.52(15) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.75(15) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.17(15) . . ?
C11 C10 H10 119.9 . . ?
C6 C11 H11 119.6 . . ?
C10 C11 C6 120.79(14) . . ?
C10 C11 H11 119.6 . . ?
H1A B1 H1B 117.2(13) . . ?
H1A B1 H1C 107.6(13) . . ?
H1B B1 H1C 108.1(14) . . ?
B2 B1 H1A 115.0(9) . . ?
B2 B1 H1B 102.0(10) . . ?
B2 B1 H1C 106.3(10) . . ?
B3 B1 H1A 117.7(9) . . ?
B3 B1 H1B 124.3(10) . . ?
B3 B1 H1C 45.3(10) . . ?
B3 B1 B2 61.93(11) . . ?
N1 B2 B1 112.26(12) . . ?
N1 B2 H2A 108.4(9) . . ?
N1 B2 H2B 107.4(10) . . ?
N1 B2 B3 114.08(13) . . ?
B1 B2 H2A 128.8(9) . . ?
B1 B2 H2B 89.5(10) . . ?
H2A B2 H2B 106.7(13) . . ?
B3 B2 B1 55.66(12) . . ?
B3 B2 H2A 80.1(9) . . ?
B3 B2 H2B 133.2(10) . . ?
B1 B3 H1C 45.3(10) . . ?
B1 B3 B2 62.40(12) . . ?
B1 B3 H3A 117.5(10) . . ?
B1 B3 H3B 125.2(10) . . ?
H1C B3 H3A 105.9(13) . . ?
H1C B3 H3B 105.4(13) . . ?
B2 B3 H1C 106.8(10) . . ?
B2 B3 H3A 116.8(10) . . ?
B2 B3 H3B 106.3(9) . . ?
H3A B3 H3B 114.9(13) . . ?
C12 N2 B5 121.26(11) . . ?
C16 N2 C12 117.66(11) . . ?
C16 N2 B5 121.07(11) . . ?
N2 C12 H12 118.8 . . ?
N2 C12 C13 122.33(12) . . ?
C13 C12 H12 118.8 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.56(12) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C17 122.33(11) . . ?
C15 C14 C13 116.31(11) . . ?
C15 C14 C17 121.35(11) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.20(12) . . ?
C16 C15 H15 119.9 . . ?
N2 C16 C15 122.83(12) . . ?
N2 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C18 C17 C14 120.15(12) . . ?
C22 C17 C14 121.16(12) . . ?
C22 C17 C18 118.69(12) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.43(14) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.25(15) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.04(14) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.88(15) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 H22 119.6 . . ?
C21 C22 C17 120.70(14) . . ?
C21 C22 H22 119.6 . . ?
H4A B4 H4B 114.1(11) . . ?
H4A B4 H4C 105.6(11) . . ?
H4B B4 H4C 107.2(11) . . ?
B5 B4 H4A 117.4(8) . . ?
B5 B4 H4B 103.8(8) . . ?
B5 B4 H4C 108.2(8) . . ?
B6 B4 H4A 118.0(8) . . ?
B6 B4 H4B 126.4(8) . . ?
B6 B4 H4C 47.2(8) . . ?
B6 B4 B5 62.13(10) . . ?
N2 B5 B4 112.37(11) . . ?
N2 B5 H5A 107.0(8) . . ?
N2 B5 H5B 107.9(8) . . ?
N2 B5 B6 112.42(11) . . ?
B4 B5 H5A 131.9(8) . . ?
B4 B5 H5B 86.9(8) . . ?
H5A B5 H5B 106.4(11) . . ?
B6 B5 B4 55.60(10) . . ?
B6 B5 H5A 84.6(8) . . ?
B6 B5 H5B 132.7(8) . . ?
B4 B6 H4C 46.3(8) . . ?
B4 B6 B5 62.27(10) . . ?
B4 B6 H6A 126.0(9) . . ?
B4 B6 H6B 117.6(8) . . ?
H4C B6 H6A 107.6(11) . . ?
H4C B6 H6B 106.7(11) . . ?
B5 B6 H4C 107.5(8) . . ?
B5 B6 H6A 103.4(9) . . ?
B5 B6 H6B 115.9(9) . . ?
H6A B6 H6B 115.2(12) . . ?

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 C1 C2 C3 0.5(2) . . . . ?
N1 B2 B3 B1 -101.37(15) . . . . ?
C1 N1 C5 C4 0.6(2) . . . . ?
C1 N1 B2 B1 70.46(17) . . . . ?
C1 N1 B2 B3 131.47(15) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
C1 C2 C3 C6 -179.08(12) . . . . ?
C2 C3 C4 C5 -2.13(19) . . . . ?
C2 C3 C6 C7 39.82(19) . . . . ?
C2 C3 C6 C11 -140.95(14) . . . . ?
C3 C4 C5 N1 1.3(2) . . . . ?
C3 C6 C7 C8 178.01(13) . . . . ?
C3 C6 C11 C10 -179.84(13) . . . . ?
C4 C3 C6 C7 -140.56(14) . . . . ?
C4 C3 C6 C11 38.67(18) . . . . ?
C5 N1 C1 C2 -1.5(2) . . . . ?
C5 N1 B2 B1 -112.78(16) . . . . ?
C5 N1 B2 B3 -51.77(19) . . . . ?
C6 C3 C4 C5 178.23(12) . . . . ?
C6 C7 C8 C9 2.0(2) . . . . ?
C7 C6 C11 C10 -0.6(2) . . . . ?
C7 C8 C9 C10 -1.0(2) . . . . ?
C8 C9 C10 C11 -0.8(2) . . . . ?
C9 C10 C11 C6 1.6(2) . . . . ?
C11 C6 C7 C8 -1.2(2) . . . . ?
B2 N1 C1 C2 175.40(13) . . . . ?
B2 N1 C5 C4 -176.28(13) . . . . ?
B3 B1 B2 N1 104.74(15) . . . . ?
N2 C12 C13 C14 -0.2(2) . . . . ?
N2 B5 B6 B4 102.50(13) . . . . ?
C12 N2 C16 C15 2.5(2) . . . . ?
C12 N2 B5 B4 -59.99(16) . . . . ?
C12 N2 B5 B6 -120.58(14) . . . . ?
C12 C13 C14 C15 2.74(19) . . . . ?
C12 C13 C14 C17 -176.35(12) . . . . ?
C13 C14 C15 C16 -2.7(2) . . . . ?
C13 C14 C17 C18 34.82(18) . . . . ?
C13 C14 C17 C22 -146.07(13) . . . . ?
C14 C15 C16 N2 0.1(2) . . . . ?
C14 C17 C18 C19 178.93(13) . . . . ?
C14 C17 C22 C21 -179.80(12) . . . . ?
C15 C14 C17 C18 -144.23(14) . . . . ?
C15 C14 C17 C22 34.88(19) . . . . ?
C16 N2 C12 C13 -2.5(2) . . . . ?
C16 N2 B5 B4 121.38(14) . . . . ?
C16 N2 B5 B6 60.79(16) . . . . ?
C17 C14 C15 C16 176.40(12) . . . . ?
C17 C18 C19 C20 1.0(2) . . . . ?
C18 C17 C22 C21 -0.7(2) . . . . ?
C18 C19 C20 C21 -1.0(2) . . . . ?
C19 C20 C21 C22 0.1(2) . . . . ?
C20 C21 C22 C17 0.7(2) . . . . ?
C22 C17 C18 C19 -0.2(2) . . . . ?
B5 N2 C12 C13 178.81(12) . . . . ?
B5 N2 C16 C15 -178.77(13) . . . . ?
B6 B4 B5 N2 -102.60(13) . . . . ?

_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
;
####################################################################### 
# 
# 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_20231123-cjxbr_auto
_database_code_depnum_ccdc_archive 'CCDC 2365387'
loop_
_audit_author_name
_audit_author_address
'chi jingxian' 'Henan Normal University '
_audit_update_record             
;
2024-12-25 deposited with the CCDC.	2025-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-12-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H13 B3 Br N'
_chemical_formula_sum            'C9 H13 B3 Br N'
_chemical_formula_weight         247.54
_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'
Br Br -0.6763 1.2805 '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                   7.0276(2)
_cell_length_b                   14.8744(4)
_cell_length_c                   11.0026(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.063(2)
_cell_angle_gamma                90
_cell_volume                     1149.37(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2694
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.1560
_cell_measurement_theta_min      5.9480
_shelx_estimated_absorpt_T_max   0.662
_shelx_estimated_absorpt_T_min   0.662
_exptl_absorpt_coefficient_mu    4.495
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4457
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.211
_diffrn_reflns_theta_min         5.002
_diffrn_ambient_temperature      293.00
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  32.00   1.00    1.00    --  -35.62  80.00 -55.00   35
  2  ω    -64.00 -35.00   1.00    1.00    --  -35.62  80.00 -55.00   29
  3  ω    119.00 174.00   1.00    1.86    --  106.81  80.00 -55.00   55
  4  ω     51.00 119.00   1.00    1.86    --  106.81 -80.00-178.00   68
  5  ω    -76.00 -43.00   1.00    1.00    --  -35.62-178.00   0.00   33
  6  ω   -108.00 -44.00   1.00    1.00    --  -35.62 178.00  30.00   64
  7  ω    -21.00  59.00   1.00    1.00    --   35.62 -80.00-178.00   80
  8  ω    -32.00   3.00   1.00    1.00    --   35.62 -57.00 -90.00   35
  9  ω      8.00  52.00   1.00    1.00    --   35.62 -57.00 -90.00   44
 10  ω     81.00 107.00   1.00    1.00    --   35.62-178.00 150.00   26
 11  ω     73.00 101.00   1.00    1.00    --   35.62 178.00-180.00   28
 12  ω    105.00 173.00   1.00    1.86    --  106.81 111.00 -90.00   68
 13  ω     99.00 125.00   1.00    1.86    --  106.81 -30.00-180.00   26
 14  ω     54.00  97.00   1.00    1.86    --  106.81-111.00 120.00   43
 15  ω     46.00  73.00   1.00    1.86    --  106.81 -30.00-180.00   27
 16  ω     41.00  66.00   1.00    1.86    --  106.81 -30.00-150.00   25
 17  ω     96.00 126.00   1.00    1.86    --  106.81 -30.00-150.00   30
 18  ω     38.00  63.00   1.00    1.86    --  106.81 -45.00-180.00   25
 19  ω    128.00 172.00   1.00    1.86    --  106.81  77.00-150.00   44
 20  ω     97.00 123.00   1.00    1.86    --  106.81 -45.00-180.00   26
 21  ω    110.00 173.00   1.00    1.86    --  106.81 111.00 150.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1985
_reflns_number_total             2176
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.770
_refine_diff_density_min         -1.125
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²+0.9787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1282
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All B(H,H,H) groups, All C(H) groups
2.a Riding coordinates:
 B1(H1A,H1B), B2(H1C,H2A,H2B), B3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_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
Br1 Br 0.73567(6) 0.61306(3) 0.26753(4) 0.0729(2) Uani 1 1 d . . . . .
N1 N 0.7174(3) 0.32052(18) 0.5645(2) 0.0451(6) Uani 1 1 d . . . . .
C1 C 0.7531(4) 0.3884(2) 0.6394(3) 0.0476(7) Uani 1 1 d . . . . .
H1 H 0.770150 0.376341 0.721999 0.057 Uiso 1 1 calc R U . . .
C2 C 0.7666(4) 0.4779(2) 0.6002(3) 0.0463(7) Uani 1 1 d . . . . .
C3 C 0.8059(5) 0.5478(3) 0.6840(3) 0.0618(9) Uani 1 1 d . . . . .
H3 H 0.820997 0.535651 0.766671 0.074 Uiso 1 1 calc R U . . .
C4 C 0.8217(6) 0.6349(3) 0.6408(4) 0.0725(11) Uani 1 1 d . . . . .
H4 H 0.846274 0.681735 0.695148 0.087 Uiso 1 1 calc R U . . .
C5 C 0.8012(5) 0.6530(3) 0.5170(4) 0.0679(10) Uani 1 1 d . . . . .
H5 H 0.814731 0.711731 0.489466 0.081 Uiso 1 1 calc R U . . .
C6 C 0.7615(4) 0.5859(2) 0.4354(3) 0.0536(7) Uani 1 1 d . . . . .
C7 C 0.7420(4) 0.4955(2) 0.4740(3) 0.0444(6) Uani 1 1 d . . . . .
C8 C 0.7011(4) 0.4224(2) 0.3970(3) 0.0485(7) Uani 1 1 d . . . . .
H8 H 0.682765 0.431654 0.313820 0.058 Uiso 1 1 calc R U . . .
C9 C 0.6883(4) 0.3385(2) 0.4434(2) 0.0474(7) Uani 1 1 d . . . . .
H9 H 0.658440 0.291213 0.390795 0.057 Uiso 1 1 calc R U . . .
B1 B 0.8109(9) 0.1365(3) 0.5237(5) 0.0782(13) Uani 1 1 d . . . . .
H1A H 0.894707 0.176102 0.456449 0.094 Uiso 1 1 d R U . . .
H1B H 0.898607 0.082802 0.577759 0.094 Uiso 1 1 d R U . . .
B2 B 0.5680(8) 0.1394(3) 0.5376(4) 0.0732(12) Uani 1 1 d . . . . .
H1C H 0.673564 0.101388 0.463940 0.088 Uiso 1 1 d R U . . .
H2A H 0.471464 0.176388 0.481940 0.088 Uiso 1 1 d R U . . .
H2B H 0.509754 0.090788 0.592640 0.088 Uiso 1 1 d R U . . .
B3 B 0.7103(7) 0.2212(3) 0.6193(3) 0.0595(10) Uani 1 1 d . . . . .
H3A H 0.829448 0.214670 0.686573 0.071 Uiso 1 1 d R U . . .
H3B H 0.555947 0.221670 0.668673 0.071 Uiso 1 1 d 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
Br1 C6 1.893(4) . ?
N1 C1 1.322(4) . ?
N1 C9 1.368(3) . ?
N1 B3 1.597(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.403(4) . ?
C2 C3 1.410(4) . ?
C2 C7 1.417(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(5) . ?
C6 C7 1.419(4) . ?
C7 C8 1.402(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.352(5) . ?
C9 H9 0.9300 . ?
B1 H1A 1.1285 . ?
B1 H1B 1.1597 . ?
B1 B2 1.720(8) . ?
B1 H1C 1.2613 . ?
B1 B3 1.802(6) . ?
B2 H1C 1.2529 . ?
B2 H2A 1.0531 . ?
B2 H2B 1.0365 . ?
B2 B3 1.796(6) . ?
B3 H3A 1.1016 . ?
B3 H3B 1.2303 . ?

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
C1 N1 C9 118.4(3) . . ?
C1 N1 B3 118.6(2) . . ?
C9 N1 B3 122.9(3) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.1(3) . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 120.8(3) . . ?
C1 C2 C7 118.0(3) . . ?
C3 C2 C7 121.2(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.8(4) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 Br1 119.8(3) . . ?
C5 C6 C7 121.0(3) . . ?
C7 C6 Br1 119.2(2) . . ?
C2 C7 C6 117.4(3) . . ?
C8 C7 C2 117.6(3) . . ?
C8 C7 C6 125.0(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
N1 C9 H9 118.7 . . ?
C8 C9 N1 122.6(3) . . ?
C8 C9 H9 118.7 . . ?
H1A B1 H1B 114.5 . . ?
H1A B1 H1C 106.4 . . ?
H1B B1 H1C 111.4 . . ?
B2 B1 H1A 126.0 . . ?
B2 B1 H1B 118.9 . . ?
B2 B1 H1C 46.6 . . ?
B2 B1 B3 61.3(3) . . ?
B3 B1 H1A 104.0 . . ?
B3 B1 H1B 113.3 . . ?
B3 B1 H1C 106.6 . . ?
B1 B2 H1C 47.1 . . ?
B1 B2 H2A 125.6 . . ?
B1 B2 H2B 116.7 . . ?
B1 B2 B3 61.6(3) . . ?
H1C B2 H2A 104.1 . . ?
H1C B2 H2B 108.6 . . ?
H2A B2 H2B 116.4 . . ?
B3 B2 H1C 107.3 . . ?
B3 B2 H2A 105.8 . . ?
B3 B2 H2B 113.9 . . ?
N1 B3 B1 114.1(3) . . ?
N1 B3 B2 117.5(3) . . ?
N1 B3 H3A 107.6 . . ?
N1 B3 H3B 101.7 . . ?
B1 B3 H3A 91.4 . . ?
B1 B3 H3B 129.2 . . ?
B2 B3 B1 57.1(3) . . ?
B2 B3 H3A 132.2 . . ?
B2 B3 H3B 75.0 . . ?
H3A B3 H3B 111.4 . . ?

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
Br1 C6 C7 C2 178.6(2) . . . . ?
Br1 C6 C7 C8 -1.0(4) . . . . ?
N1 C1 C2 C3 -179.7(3) . . . . ?
N1 C1 C2 C7 -0.5(4) . . . . ?
C1 N1 C9 C8 2.3(5) . . . . ?
C1 N1 B3 B1 -142.2(3) . . . . ?
C1 N1 B3 B2 153.8(3) . . . . ?
C1 C2 C3 C4 178.7(3) . . . . ?
C1 C2 C7 C6 -178.2(3) . . . . ?
C1 C2 C7 C8 1.5(4) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C2 C7 C8 C9 -0.7(4) . . . . ?
C3 C2 C7 C6 1.0(4) . . . . ?
C3 C2 C7 C8 -179.3(3) . . . . ?
C3 C4 C5 C6 1.3(6) . . . . ?
C4 C5 C6 Br1 -179.7(3) . . . . ?
C4 C5 C6 C7 -0.7(5) . . . . ?
C5 C6 C7 C2 -0.5(4) . . . . ?
C5 C6 C7 C8 179.9(3) . . . . ?
C6 C7 C8 C9 179.0(3) . . . . ?
C7 C2 C3 C4 -0.5(5) . . . . ?
C7 C8 C9 N1 -1.3(5) . . . . ?
C9 N1 C1 C2 -1.4(5) . . . . ?
C9 N1 B3 B1 37.8(5) . . . . ?
C9 N1 B3 B2 -26.2(5) . . . . ?
B1 B2 B3 N1 102.2(4) . . . . ?
B2 B1 B3 N1 -108.3(3) . . . . ?
B3 N1 C1 C2 178.6(3) . . . . ?
B3 N1 C9 C8 -177.6(3) . . . . ?

_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
;
