# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_y
_database_code_depnum_ccdc_archive 'CCDC 2406846'
loop_
_audit_author_name
_audit_author_address
meng
;china jiliang university
China
;
_audit_update_record             
;
2024-12-02 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;
_audit_creation_date             2024-12-02
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C12 H15 B N6)'
_chemical_formula_sum            'C24 H30 B2 N12'
_chemical_formula_weight         508.22
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.861(6)
_cell_length_b                   13.916(5)
_cell_length_c                   13.706(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.314(6)
_cell_angle_gamma                90
_cell_volume                     2705.9(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3476
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.78
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.13
_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  0.0351
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11956
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.382
_diffrn_reflns_theta_min         2.050
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2345
_reflns_number_total             3373
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0017(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.022
_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)+(0.0805P)²+0.6732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1550
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All B(H,H) groups, All C(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 B1(H1A,H1B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11) 
2.c Idealised Me refined as rotating group: 
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
; 
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.035 
;
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
B1 B 0.11585(12) 0.06152(14) 0.13216(14) 0.0544(4) Uani 1 1 d . . . . .
H1A H 0.0830 0.0008 0.1292 0.065 Uiso 1 1 calc R . . . .
H1B H 0.0809 0.1008 0.0750 0.065 Uiso 1 1 calc R . . . .
C1 C 0.44197(10) 0.11241(11) 0.11398(10) 0.0481(4) Uani 1 1 d . . . . .
C2 C 0.44857(12) 0.21125(13) 0.11040(13) 0.0615(4) Uani 1 1 d . . . . .
H2 H 0.3963 0.2490 0.1077 0.074 Uiso 1 1 calc R . . . .
C3 C 0.53246(13) 0.25426(16) 0.11085(15) 0.0760(5) Uani 1 1 d . . . . .
H3 H 0.5364 0.3209 0.1090 0.091 Uiso 1 1 calc R . . . .
C4 C 0.60929(13) 0.19990(18) 0.11398(15) 0.0794(6) Uani 1 1 d . . . . .
H4 H 0.6657 0.2293 0.1146 0.095 Uiso 1 1 calc R . . . .
C5 C 0.60339(13) 0.1023(2) 0.11615(17) 0.0868(6) Uani 1 1 d . . . . .
H5 H 0.6558 0.0652 0.1175 0.104 Uiso 1 1 calc R . . . .
C6 C 0.52028(13) 0.05792(15) 0.11640(15) 0.0716(5) Uani 1 1 d . . . . .
H6 H 0.5171 -0.0088 0.1182 0.086 Uiso 1 1 calc R . . . .
C7 C 0.35414(10) 0.06610(10) 0.11814(10) 0.0462(3) Uani 1 1 d . . . . .
C8 C 0.12315(9) 0.11520(10) 0.23752(11) 0.0461(3) Uani 1 1 d . . . . .
C10 C 0.13326(11) 0.14427(13) 0.40061(12) 0.0588(4) Uani 1 1 d . . . . .
H10 H 0.1376 0.1341 0.4689 0.071 Uiso 1 1 calc R . . . .
C11 C 0.12950(11) 0.22912(12) 0.35458(13) 0.0574(4) Uani 1 1 d . . . . .
H11 H 0.1307 0.2893 0.3844 0.069 Uiso 1 1 calc R . . . .
C12 C 0.13550(14) -0.02814(12) 0.35013(15) 0.0687(5) Uani 1 1 d . . . . .
H12A H 0.1143 -0.0632 0.2871 0.103 Uiso 1 1 calc GR . . . .
H12B H 0.0965 -0.0438 0.3925 0.103 Uiso 1 1 calc GR . . . .
H12C H 0.1997 -0.0451 0.3849 0.103 Uiso 1 1 calc GR . . . .
C13 C 0.12102(14) 0.28421(12) 0.17770(15) 0.0737(5) Uani 1 1 d . . . . .
H13A H 0.1690 0.2712 0.1455 0.111 Uiso 1 1 calc GR . . . .
H13B H 0.1321 0.3460 0.2102 0.111 Uiso 1 1 calc GR . . . .
H13C H 0.0603 0.2839 0.1271 0.111 Uiso 1 1 calc GR . . . .
N1 N 0.34451(11) -0.02894(9) 0.12822(12) 0.0638(4) Uani 1 1 d . . . . .
N2 N 0.25761(11) -0.04152(9) 0.13344(12) 0.0633(4) Uani 1 1 d . . . . .
N3 N 0.21774(9) 0.04349(9) 0.12597(9) 0.0484(3) Uani 1 1 d . . . . .
N4 N 0.27625(9) 0.11334(9) 0.11616(9) 0.0498(3) Uani 1 1 d . . . . .
N5 N 0.12954(8) 0.07472(9) 0.32866(9) 0.0491(3) Uani 1 1 d . . . . .
N6 N 0.12350(8) 0.21016(9) 0.25441(9) 0.0506(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 H1A 0.9700 . ?
B1 H1B 0.9700 . ?
B1 C8 1.601(2) . ?
B1 N3 1.562(2) . ?
C1 C2 1.381(2) . ?
C1 C6 1.381(2) . ?
C1 C7 1.472(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.360(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.342(2) . ?
C7 N4 1.3243(18) . ?
C8 N5 1.3477(18) . ?
C8 N6 1.3413(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.332(2) . ?
C10 N5 1.371(2) . ?
C11 H11 0.9300 . ?
C11 N6 1.375(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 N5 1.459(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 N6 1.465(2) . ?
N1 N2 1.326(2) . ?
N2 N3 1.3133(18) . ?
N3 N4 1.3373(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A B1 H1B 108.4 . . ?
C8 B1 H1A 110.0 . . ?
C8 B1 H1B 110.0 . . ?
N3 B1 H1A 110.0 . . ?
N3 B1 H1B 110.0 . . ?
N3 B1 C8 108.51(12) . . ?
C2 C1 C6 118.66(15) . . ?
C2 C1 C7 120.70(13) . . ?
C6 C1 C7 120.62(16) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.33(17) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.78(18) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.61(19) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.1(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C1 123.95(13) . . ?
N4 C7 C1 124.17(13) . . ?
N4 C7 N1 111.84(13) . . ?
N5 C8 B1 127.47(14) . . ?
N6 C8 B1 127.68(13) . . ?
N6 C8 N5 104.84(13) . . ?
C11 C10 H10 126.3 . . ?
C11 C10 N5 107.34(14) . . ?
N5 C10 H10 126.3 . . ?
C10 C11 H11 126.8 . . ?
C10 C11 N6 106.50(14) . . ?
N6 C11 H11 126.8 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N6 C13 H13A 109.5 . . ?
N6 C13 H13B 109.5 . . ?
N6 C13 H13C 109.5 . . ?
N2 N1 C7 105.74(12) . . ?
N3 N2 N1 107.50(12) . . ?
N2 N3 B1 124.24(13) . . ?
N2 N3 N4 111.77(13) . . ?
N4 N3 B1 123.95(12) . . ?
C7 N4 N3 103.15(12) . . ?
C8 N5 C10 110.38(14) . . ?
C8 N5 C12 125.48(13) . . ?
C10 N5 C12 124.10(14) . . ?
C8 N6 C11 110.93(13) . . ?
C8 N6 C13 124.84(14) . . ?
C11 N6 C13 124.20(14) . . ?

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

data_220603znn1_0m
_database_code_depnum_ccdc_archive 'CCDC 2451381'
loop_
_audit_author_name
_audit_author_address
'chang hong'
;china jiliang unoversity
China
;
_audit_update_record             
;
2025-05-15 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;
_audit_creation_date             2022-06-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 B N3'
_chemical_formula_sum            'C17 H18 B N3'
_chemical_formula_weight         275.15
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   15.575(5)
_cell_length_b                   8.029(3)
_cell_length_c                   25.514(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.777(6)
_cell_angle_gamma                90
_cell_volume                     3111.6(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2220
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.00
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1271 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.7119.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            16821
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.408
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3095
_reflns_number_total             6326
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1560
_refine_ls_R_factor_gt           0.0715
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0987P)²+0.9703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.2315
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 B014(H01G,H01H), B016(H01O,H01P)
2.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C012(H012)
2.c Idealised Me refined as rotating group:
 C010(H01A,H01B,H01C), C011(H01D,H01E,H01F), C013(H01I,H01J,H01K), C015(H01L,
 H01M,H01N)
;
_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
N001 N 0.35567(16) -0.0573(3) 0.34349(10) 0.0552(7) Uani 1 1 d . . . . .
N002 N 0.43311(18) 0.2970(4) 0.38007(10) 0.0620(7) Uani 1 1 d . . . . .
N003 N 1.01723(17) 0.2629(4) 0.37125(11) 0.0673(8) Uani 1 1 d . . . . .
N004 N 0.86229(15) 0.6156(4) 0.39008(11) 0.0618(7) Uani 1 1 d . . . . .
N005 N 0.55247(17) 0.2504(4) 0.35448(11) 0.0674(8) Uani 1 1 d . . . . .
N006 N 0.91791(19) 0.2390(4) 0.41643(12) 0.0711(8) Uani 1 1 d . . . . .
C007 C 0.72086(18) 0.6808(4) 0.34693(12) 0.0497(7) Uani 1 1 d . . . . .
C008 C 0.73621(19) 0.7457(4) 0.40097(12) 0.0519(8) Uani 1 1 d . . . . .
C009 C 0.7994(2) 0.6013(4) 0.34193(13) 0.0553(8) Uani 1 1 d . . . . .
C00A C 0.4733(2) 0.1837(4) 0.35528(12) 0.0547(8) Uani 1 1 d . . . . .
C00B C 0.2718(2) -0.0531(4) 0.31051(13) 0.0554(8) Uani 1 1 d . . . . .
C00C C 0.3493(2) -0.1439(4) 0.38880(13) 0.0588(8) Uani 1 1 d . . . . .
C00D C 0.96305(19) 0.3527(5) 0.39474(13) 0.0600(9) Uani 1 1 d . . . . .
C00E C 0.2625(2) -0.2033(4) 0.38532(13) 0.0615(9) Uani 1 1 d . . . . .
C00F C 0.2125(2) -0.1428(4) 0.33394(13) 0.0588(9) Uani 1 1 d . . . . .
C00G C 0.8231(2) 0.7006(4) 0.42592(13) 0.0592(8) Uani 1 1 d . . . . .
C00H C 0.6482(2) 0.6805(4) 0.30339(13) 0.0645(9) Uani 1 1 d . . . . .
H00H H 0.596305 0.734112 0.305819 0.077 Uiso 1 1 calc R U . . .
C00I C 0.6852(2) 0.8317(5) 0.42986(14) 0.0699(10) Uani 1 1 d . . . . .
H00I H 0.627488 0.860158 0.413900 0.084 Uiso 1 1 calc R U . . .
C00J C 0.2440(2) 0.0302(5) 0.26175(14) 0.0715(10) Uani 1 1 d . . . . .
H00J H 0.283355 0.089990 0.246414 0.086 Uiso 1 1 calc R U . . .
C00K C 0.4875(3) 0.4340(5) 0.39459(14) 0.0841(12) Uani 1 1 d . . . . .
H00K H 0.474525 0.529075 0.412164 0.101 Uiso 1 1 calc R U . . .
C00L C 0.2430(3) -0.2942(5) 0.42693(17) 0.0845(12) Uani 1 1 d . . . . .
H00L H 0.186143 -0.333679 0.424581 0.101 Uiso 1 1 calc R U . . .
C00M C 0.6549(3) 0.5994(5) 0.25690(14) 0.0763(11) Uani 1 1 d . . . . .
H00M H 0.606841 0.596428 0.227823 0.092 Uiso 1 1 calc R U . . .
C00N C 0.8057(2) 0.5222(5) 0.29519(15) 0.0746(10) Uani 1 1 d . . . . .
H00N H 0.857685 0.470298 0.292066 0.089 Uiso 1 1 calc R U . . .
C00O C 0.8580(2) 0.7446(5) 0.47975(15) 0.0783(11) Uani 1 1 d . . . . .
H00O H 0.915187 0.715782 0.496871 0.094 Uiso 1 1 calc R U . . .
C00P C 0.1243(2) -0.1552(5) 0.30641(18) 0.0787(11) Uani 1 1 d . . . . .
H00P H 0.084588 -0.219161 0.320155 0.094 Uiso 1 1 calc R U . . .
C00Q C 0.5610(3) 0.4038(6) 0.37877(16) 0.0897(13) Uani 1 1 d . . . . .
H00Q H 0.609697 0.473606 0.383250 0.108 Uiso 1 1 calc R U . . .
C00R C 0.4145(3) -0.1721(5) 0.43535(15) 0.0830(12) Uani 1 1 d . . . . .
H00R H 0.471225 -0.130456 0.438956 0.100 Uiso 1 1 calc R U . . .
C00S C 0.9435(3) 0.0816(6) 0.40638(17) 0.0900(12) Uani 1 1 d . . . . .
H00S H 0.921236 -0.017291 0.416956 0.108 Uiso 1 1 calc R U . . .
C00T C 1.0056(3) 0.0959(6) 0.37885(17) 0.0884(12) Uani 1 1 d . . . . .
H00T H 1.035869 0.009047 0.366871 0.106 Uiso 1 1 calc R U . . .
C00U C 0.7334(3) 0.5217(5) 0.25332(15) 0.0815(11) Uani 1 1 d . . . . .
H00U H 0.736893 0.467931 0.221561 0.098 Uiso 1 1 calc R U . . .
C00V C 0.0976(3) -0.0708(6) 0.25865(19) 0.0911(13) Uani 1 1 d . . . . .
H00V H 0.038826 -0.075417 0.240534 0.109 Uiso 1 1 calc R U . . .
C00W C 0.3071(4) -0.3264(6) 0.47153(19) 0.1036(16) Uani 1 1 d . . . . .
H00W H 0.294070 -0.390301 0.499170 0.124 Uiso 1 1 calc R U . . .
C00X C 0.7204(3) 0.8750(5) 0.48236(16) 0.0892(12) Uani 1 1 d . . . . .
H00X H 0.686550 0.934241 0.501747 0.107 Uiso 1 1 calc R U . . .
C00Y C 0.8044(3) 0.8319(5) 0.50610(16) 0.0889(12) Uani 1 1 d . . . . .
H00Y H 0.826483 0.862788 0.541661 0.107 Uiso 1 1 calc R U . . .
C00Z C 0.1563(3) 0.0203(6) 0.23730(16) 0.0914(13) Uani 1 1 d . . . . .
H00Z H 0.135942 0.077224 0.205202 0.110 Uiso 1 1 calc R U . . .
C010 C 0.3435(3) 0.2911(5) 0.38826(18) 0.0948(13) Uani 1 1 d . . . . .
H01A H 0.302975 0.277138 0.354247 0.142 Uiso 1 1 calc R U . . .
H01B H 0.330604 0.393116 0.404588 0.142 Uiso 1 1 calc R U . . .
H01C H 0.337854 0.199216 0.411326 0.142 Uiso 1 1 calc R U . . .
C011 C 0.6166(2) 0.1738(6) 0.32762(19) 0.1025(15) Uani 1 1 d . . . . .
H01D H 0.648933 0.089313 0.350397 0.154 Uiso 1 1 calc R U . . .
H01E H 0.656666 0.257383 0.320513 0.154 Uiso 1 1 calc R U . . .
H01F H 0.586368 0.124593 0.294362 0.154 Uiso 1 1 calc R U . . .
C012 C 0.3909(4) -0.2651(6) 0.47604(16) 0.1028(16) Uani 1 1 d . . . . .
H012 H 0.433174 -0.286422 0.507258 0.123 Uiso 1 1 calc R U . . .
C013 C 1.0793(3) 0.3324(6) 0.34179(18) 0.1025(14) Uani 1 1 d . . . . .
H01I H 1.047992 0.398686 0.312426 0.154 Uiso 1 1 calc R U . . .
H01J H 1.109290 0.243388 0.328127 0.154 Uiso 1 1 calc R U . . .
H01K H 1.121522 0.400629 0.365466 0.154 Uiso 1 1 calc R U . . .
B014 B 0.4414(2) 0.0072(5) 0.33011(17) 0.0666(11) Uani 1 1 d . . . . .
H01G H 0.433050 0.014323 0.291360 0.080 Uiso 1 1 calc R U . . .
H01H H 0.487685 -0.073545 0.342779 0.080 Uiso 1 1 calc R U . . .
C015 C 0.8536(3) 0.2770(6) 0.44789(18) 0.1016(15) Uani 1 1 d . . . . .
H01L H 0.880136 0.346070 0.477811 0.152 Uiso 1 1 calc R U . . .
H01M H 0.833272 0.175414 0.460871 0.152 Uiso 1 1 calc R U . . .
H01N H 0.804698 0.334754 0.425845 0.152 Uiso 1 1 calc R U . . .
B016 B 0.9584(2) 0.5517(6) 0.3986(2) 0.0810(14) Uani 1 1 d . . . . .
H01O H 0.991333 0.587446 0.433584 0.097 Uiso 1 1 calc R U . . .
H01P H 0.985767 0.600835 0.371595 0.097 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
N001 C00B 1.389(4) . ?
N001 C00C 1.371(4) . ?
N001 B014 1.539(4) . ?
N002 C00A 1.340(4) . ?
N002 C00K 1.387(5) . ?
N002 C010 1.457(4) . ?
N003 C00D 1.347(4) . ?
N003 C00T 1.373(5) . ?
N003 C013 1.460(5) . ?
N004 C009 1.396(4) . ?
N004 C00G 1.386(4) . ?
N004 B016 1.551(4) . ?
N005 C00A 1.349(4) . ?
N005 C00Q 1.372(5) . ?
N005 C011 1.466(5) . ?
N006 C00D 1.344(4) . ?
N006 C00S 1.366(5) . ?
N006 C015 1.448(4) . ?
C007 C008 1.444(4) . ?
C007 C009 1.410(4) . ?
C007 C00H 1.399(4) . ?
C008 C00G 1.410(4) . ?
C008 C00I 1.382(4) . ?
C009 C00N 1.374(5) . ?
C00A B014 1.590(5) . ?
C00B C00F 1.404(4) . ?
C00B C00J 1.394(5) . ?
C00C C00E 1.417(4) . ?
C00C C00R 1.400(5) . ?
C00D B016 1.603(6) . ?
C00E C00F 1.452(5) . ?
C00E C00L 1.377(5) . ?
C00F C00P 1.402(5) . ?
C00G C00O 1.406(5) . ?
C00H H00H 0.9300 . ?
C00H C00M 1.377(5) . ?
C00I H00I 0.9300 . ?
C00I C00X 1.375(5) . ?
C00J H00J 0.9300 . ?
C00J C00Z 1.373(5) . ?
C00K H00K 0.9300 . ?
C00K C00Q 1.318(5) . ?
C00L H00L 0.9300 . ?
C00L C00W 1.362(6) . ?
C00M H00M 0.9300 . ?
C00M C00U 1.395(5) . ?
C00N H00N 0.9300 . ?
C00N C00U 1.369(5) . ?
C00O H00O 0.9300 . ?
C00O C00Y 1.375(5) . ?
C00P H00P 0.9300 . ?
C00P C00V 1.376(6) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C012 1.392(6) . ?
C00S H00S 0.9300 . ?
C00S C00T 1.320(5) . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?
C00V H00V 0.9300 . ?
C00V C00Z 1.375(6) . ?
C00W H00W 0.9300 . ?
C00W C012 1.376(6) . ?
C00X H00X 0.9300 . ?
C00X C00Y 1.359(5) . ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C010 H01A 0.9600 . ?
C010 H01B 0.9600 . ?
C010 H01C 0.9600 . ?
C011 H01D 0.9600 . ?
C011 H01E 0.9600 . ?
C011 H01F 0.9600 . ?
C012 H012 0.9300 . ?
C013 H01I 0.9600 . ?
C013 H01J 0.9600 . ?
C013 H01K 0.9600 . ?
B014 H01G 0.9700 . ?
B014 H01H 0.9700 . ?
C015 H01L 0.9600 . ?
C015 H01M 0.9600 . ?
C015 H01N 0.9600 . ?
B016 H01O 0.9700 . ?
B016 H01P 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00B N001 B014 127.1(3) . . ?
C00C N001 C00B 106.8(3) . . ?
C00C N001 B014 125.8(3) . . ?
C00A N002 C00K 110.1(3) . . ?
C00A N002 C010 127.4(3) . . ?
C00K N002 C010 122.4(3) . . ?
C00D N003 C00T 110.2(3) . . ?
C00D N003 C013 125.2(3) . . ?
C00T N003 C013 124.6(4) . . ?
C009 N004 B016 124.3(3) . . ?
C00G N004 C009 107.2(2) . . ?
C00G N004 B016 128.5(3) . . ?
C00A N005 C00Q 110.3(3) . . ?
C00A N005 C011 124.1(3) . . ?
C00Q N005 C011 125.4(4) . . ?
C00D N006 C00S 110.5(3) . . ?
C00D N006 C015 125.0(3) . . ?
C00S N006 C015 124.4(4) . . ?
C009 C007 C008 106.6(3) . . ?
C00H C007 C008 133.9(3) . . ?
C00H C007 C009 119.5(3) . . ?
C00G C008 C007 106.2(3) . . ?
C00I C008 C007 134.2(3) . . ?
C00I C008 C00G 119.7(3) . . ?
N004 C009 C007 109.7(3) . . ?
C00N C009 N004 129.1(3) . . ?
C00N C009 C007 121.2(3) . . ?
N002 C00A N005 105.2(3) . . ?
N002 C00A B014 131.3(3) . . ?
N005 C00A B014 123.6(3) . . ?
N001 C00B C00F 110.4(3) . . ?
N001 C00B C00J 128.1(3) . . ?
C00J C00B C00F 121.5(3) . . ?
N001 C00C C00E 111.3(3) . . ?
N001 C00C C00R 128.6(3) . . ?
C00R C00C C00E 120.1(3) . . ?
N003 C00D B016 127.0(3) . . ?
N006 C00D N003 104.8(3) . . ?
N006 C00D B016 128.1(3) . . ?
C00C C00E C00F 104.9(3) . . ?
C00L C00E C00C 120.0(4) . . ?
C00L C00E C00F 135.0(4) . . ?
C00B C00F C00E 106.5(3) . . ?
C00P C00F C00B 119.1(3) . . ?
C00P C00F C00E 134.4(3) . . ?
N004 C00G C008 110.3(3) . . ?
N004 C00G C00O 129.6(3) . . ?
C00O C00G C008 120.1(3) . . ?
C007 C00H H00H 120.6 . . ?
C00M C00H C007 118.9(3) . . ?
C00M C00H H00H 120.6 . . ?
C008 C00I H00I 120.2 . . ?
C00X C00I C008 119.6(3) . . ?
C00X C00I H00I 120.2 . . ?
C00B C00J H00J 121.3 . . ?
C00Z C00J C00B 117.3(4) . . ?
C00Z C00J H00J 121.3 . . ?
N002 C00K H00K 126.5 . . ?
C00Q C00K N002 107.0(4) . . ?
C00Q C00K H00K 126.5 . . ?
C00E C00L H00L 120.0 . . ?
C00W C00L C00E 119.9(4) . . ?
C00W C00L H00L 120.0 . . ?
C00H C00M H00M 119.9 . . ?
C00H C00M C00U 120.2(3) . . ?
C00U C00M H00M 119.9 . . ?
C009 C00N H00N 120.8 . . ?
C00U C00N C009 118.3(3) . . ?
C00U C00N H00N 120.8 . . ?
C00G C00O H00O 121.3 . . ?
C00Y C00O C00G 117.4(3) . . ?
C00Y C00O H00O 121.3 . . ?
C00F C00P H00P 120.7 . . ?
C00V C00P C00F 118.7(4) . . ?
C00V C00P H00P 120.7 . . ?
N005 C00Q H00Q 126.3 . . ?
C00K C00Q N005 107.5(4) . . ?
C00K C00Q H00Q 126.3 . . ?
C00C C00R H00R 121.4 . . ?
C012 C00R C00C 117.3(4) . . ?
C012 C00R H00R 121.4 . . ?
N006 C00S H00S 126.3 . . ?
C00T C00S N006 107.3(4) . . ?
C00T C00S H00S 126.3 . . ?
N003 C00T H00T 126.4 . . ?
C00S C00T N003 107.1(4) . . ?
C00S C00T H00T 126.4 . . ?
C00M C00U H00U 119.0 . . ?
C00N C00U C00M 121.9(3) . . ?
C00N C00U H00U 119.0 . . ?
C00P C00V H00V 119.5 . . ?
C00Z C00V C00P 121.0(4) . . ?
C00Z C00V H00V 119.5 . . ?
C00L C00W H00W 119.7 . . ?
C00L C00W C012 120.6(4) . . ?
C012 C00W H00W 119.7 . . ?
C00I C00X H00X 119.8 . . ?
C00Y C00X C00I 120.5(4) . . ?
C00Y C00X H00X 119.8 . . ?
C00O C00Y H00Y 118.6 . . ?
C00X C00Y C00O 122.7(4) . . ?
C00X C00Y H00Y 118.6 . . ?
C00J C00Z C00V 122.2(4) . . ?
C00J C00Z H00Z 118.9 . . ?
C00V C00Z H00Z 118.9 . . ?
N002 C010 H01A 109.5 . . ?
N002 C010 H01B 109.5 . . ?
N002 C010 H01C 109.5 . . ?
H01A C010 H01B 109.5 . . ?
H01A C010 H01C 109.5 . . ?
H01B C010 H01C 109.5 . . ?
N005 C011 H01D 109.5 . . ?
N005 C011 H01E 109.5 . . ?
N005 C011 H01F 109.5 . . ?
H01D C011 H01E 109.5 . . ?
H01D C011 H01F 109.5 . . ?
H01E C011 H01F 109.5 . . ?
C00R C012 H012 119.0 . . ?
C00W C012 C00R 122.1(4) . . ?
C00W C012 H012 119.0 . . ?
N003 C013 H01I 109.5 . . ?
N003 C013 H01J 109.5 . . ?
N003 C013 H01K 109.5 . . ?
H01I C013 H01J 109.5 . . ?
H01I C013 H01K 109.5 . . ?
H01J C013 H01K 109.5 . . ?
N001 B014 C00A 114.8(3) . . ?
N001 B014 H01G 108.6 . . ?
N001 B014 H01H 108.6 . . ?
C00A B014 H01G 108.6 . . ?
C00A B014 H01H 108.6 . . ?
H01G B014 H01H 107.5 . . ?
N006 C015 H01L 109.5 . . ?
N006 C015 H01M 109.5 . . ?
N006 C015 H01N 109.5 . . ?
H01L C015 H01M 109.5 . . ?
H01L C015 H01N 109.5 . . ?
H01M C015 H01N 109.5 . . ?
N004 B016 C00D 112.1(3) . . ?
N004 B016 H01O 109.2 . . ?
N004 B016 H01P 109.2 . . ?
C00D B016 H01O 109.2 . . ?
C00D B016 H01P 109.2 . . ?
H01O B016 H01P 107.9 . . ?

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
N001 C00B C00F C00E 1.3(3) . . . . ?
N001 C00B C00F C00P -179.2(3) . . . . ?
N001 C00B C00J C00Z -177.7(3) . . . . ?
N001 C00C C00E C00F -1.5(3) . . . . ?
N001 C00C C00E C00L 179.7(3) . . . . ?
N001 C00C C00R C012 -180.0(3) . . . . ?
N002 C00A B014 N001 -10.3(5) . . . . ?
N002 C00K C00Q N005 0.3(4) . . . . ?
N003 C00D B016 N004 140.2(3) . . . . ?
N004 C009 C00N C00U 178.4(3) . . . . ?
N004 C00G C00O C00Y 179.1(4) . . . . ?
N005 C00A B014 N001 170.5(3) . . . . ?
N006 C00D B016 N004 -43.8(5) . . . . ?
N006 C00S C00T N003 -1.0(5) . . . . ?
C007 C008 C00G N004 1.3(4) . . . . ?
C007 C008 C00G C00O -179.3(3) . . . . ?
C007 C008 C00I C00X 179.3(4) . . . . ?
C007 C009 C00N C00U -0.2(5) . . . . ?
C007 C00H C00M C00U -1.1(5) . . . . ?
C008 C007 C009 N004 -0.5(3) . . . . ?
C008 C007 C009 C00N 178.3(3) . . . . ?
C008 C007 C00H C00M -177.3(3) . . . . ?
C008 C00G C00O C00Y -0.1(5) . . . . ?
C008 C00I C00X C00Y -0.9(6) . . . . ?
C009 N004 C00G C008 -1.7(4) . . . . ?
C009 N004 C00G C00O 179.0(3) . . . . ?
C009 N004 B016 C00D -65.7(5) . . . . ?
C009 C007 C008 C00G -0.5(3) . . . . ?
C009 C007 C008 C00I -178.8(4) . . . . ?
C009 C007 C00H C00M 1.2(5) . . . . ?
C009 C00N C00U C00M 0.4(6) . . . . ?
C00A N002 C00K C00Q -0.2(4) . . . . ?
C00A N005 C00Q C00K -0.3(4) . . . . ?
C00B N001 C00C C00E 2.4(3) . . . . ?
C00B N001 C00C C00R -175.3(3) . . . . ?
C00B N001 B014 C00A 101.0(4) . . . . ?
C00B C00F C00P C00V -3.7(5) . . . . ?
C00B C00J C00Z C00V -1.6(6) . . . . ?
C00C N001 C00B C00F -2.3(3) . . . . ?
C00C N001 C00B C00J 175.3(3) . . . . ?
C00C N001 B014 C00A -85.4(4) . . . . ?
C00C C00E C00F C00B 0.1(3) . . . . ?
C00C C00E C00F C00P -179.2(3) . . . . ?
C00C C00E C00L C00W 0.3(5) . . . . ?
C00C C00R C012 C00W -0.6(6) . . . . ?
C00D N003 C00T C00S 0.9(4) . . . . ?
C00D N006 C00S C00T 0.8(5) . . . . ?
C00E C00C C00R C012 2.5(5) . . . . ?
C00E C00F C00P C00V 175.6(4) . . . . ?
C00E C00L C00W C012 1.7(6) . . . . ?
C00F C00B C00J C00Z -0.4(5) . . . . ?
C00F C00E C00L C00W -178.1(4) . . . . ?
C00F C00P C00V C00Z 1.8(6) . . . . ?
C00G N004 C009 C007 1.3(3) . . . . ?
C00G N004 C009 C00N -177.4(3) . . . . ?
C00G N004 B016 C00D 117.0(4) . . . . ?
C00G C008 C00I C00X 1.1(5) . . . . ?
C00G C00O C00Y C00X 0.4(6) . . . . ?
C00H C007 C008 C00G 178.2(3) . . . . ?
C00H C007 C008 C00I -0.1(6) . . . . ?
C00H C007 C009 N004 -179.4(3) . . . . ?
C00H C007 C009 C00N -0.6(5) . . . . ?
C00H C00M C00U C00N 0.3(6) . . . . ?
C00I C008 C00G N004 179.9(3) . . . . ?
C00I C008 C00G C00O -0.7(5) . . . . ?
C00I C00X C00Y C00O 0.0(7) . . . . ?
C00J C00B C00F C00E -176.4(3) . . . . ?
C00J C00B C00F C00P 3.0(5) . . . . ?
C00K N002 C00A N005 0.0(3) . . . . ?
C00K N002 C00A B014 -179.3(3) . . . . ?
C00L C00E C00F C00B 178.6(4) . . . . ?
C00L C00E C00F C00P -0.7(7) . . . . ?
C00L C00W C012 C00R -1.6(7) . . . . ?
C00P C00V C00Z C00J 0.9(6) . . . . ?
C00Q N005 C00A N002 0.1(3) . . . . ?
C00Q N005 C00A B014 179.5(3) . . . . ?
C00R C00C C00E C00F 176.4(3) . . . . ?
C00R C00C C00E C00L -2.4(5) . . . . ?
C00S N006 C00D N003 -0.2(4) . . . . ?
C00S N006 C00D B016 -177.0(4) . . . . ?
C00T N003 C00D N006 -0.4(4) . . . . ?
C00T N003 C00D B016 176.4(3) . . . . ?
C010 N002 C00A N005 175.6(3) . . . . ?
C010 N002 C00A B014 -3.7(6) . . . . ?
C010 N002 C00K C00Q -176.0(3) . . . . ?
C011 N005 C00A N002 -175.5(3) . . . . ?
C011 N005 C00A B014 3.9(5) . . . . ?
C011 N005 C00Q C00K 175.3(3) . . . . ?
C013 N003 C00D N006 179.5(3) . . . . ?
C013 N003 C00D B016 -3.7(5) . . . . ?
C013 N003 C00T C00S -179.0(4) . . . . ?
B014 N001 C00B C00F 172.3(3) . . . . ?
B014 N001 C00B C00J -10.1(5) . . . . ?
B014 N001 C00C C00E -172.3(3) . . . . ?
B014 N001 C00C C00R 10.0(5) . . . . ?
C015 N006 C00D N003 177.5(3) . . . . ?
C015 N006 C00D B016 0.8(6) . . . . ?
C015 N006 C00S C00T -177.0(4) . . . . ?
B016 N004 C009 C007 -176.5(3) . . . . ?
B016 N004 C009 C00N 4.8(5) . . . . ?
B016 N004 C00G C008 176.0(3) . . . . ?
B016 N004 C00G C00O -3.3(6) . . . . ?

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

data_y_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2412782'
loop_
_audit_author_name
_audit_author_address
'chang hong'
;china jiliang university
China
;
_audit_update_record             
;
2024-12-24 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;
_audit_creation_date             2024-12-20
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H15 B N6'
_chemical_formula_sum            'C12 H15 B N6'
_chemical_formula_weight         254.11
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   15.699(3)
_cell_length_b                   6.1877(13)
_cell_length_c                   14.634(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.537(3)
_cell_angle_gamma                90
_cell_volume                     1339.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5139
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      30.87
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13686
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.421
_diffrn_reflns_theta_min         2.753
_diffrn_ambient_temperature      293(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3185
_reflns_number_total             4309
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         4309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.029
_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)+(0.0917P)²+0.1120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1551
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All B(H,H) groups, All C(H,H,H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10) 
2.b Idealised Me refined as rotating group: 
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C) 
;
_atom_sites_solution_hydrogens   mixed
_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
B1 B 0.76211(8) 0.8147(2) 0.70886(9) 0.0382(3) Uani 1 1 d . . . . .
H1A H 0.6890(9) 0.807(3) 0.6595(11) 0.057 Uiso 1 1 d R . . . .
H1B H 0.7818(10) 0.984(3) 0.7370(11) 0.057 Uiso 1 1 d R . . . .
C1 C 0.65142(7) 0.74118(18) 0.86373(7) 0.0349(2) Uani 1 1 d . . . . .
C2 C 0.62881(8) 0.94729(19) 0.82509(8) 0.0410(3) Uani 1 1 d . . . . .
H2 H 0.6651 1.0163 0.7952 0.049 Uiso 1 1 calc R . . . .
C3 C 0.55222(8) 1.0502(2) 0.83109(9) 0.0485(3) Uani 1 1 d . . . . .
H3 H 0.5374 1.1876 0.8048 0.058 Uiso 1 1 calc R . . . .
C4 C 0.49819(9) 0.9511(3) 0.87543(10) 0.0572(4) Uani 1 1 d . . . . .
H4 H 0.4469 1.0207 0.8789 0.069 Uiso 1 1 calc R . . . .
C5 C 0.52040(9) 0.7474(3) 0.91490(11) 0.0607(4) Uani 1 1 d . . . . .
H5 H 0.4840 0.6803 0.9452 0.073 Uiso 1 1 calc R . . . .
C6 C 0.59647(8) 0.6429(2) 0.90960(9) 0.0474(3) Uani 1 1 d . . . . .
H6 H 0.6112 0.5062 0.9368 0.057 Uiso 1 1 calc R . . . .
C7 C 0.73172(7) 0.62510(17) 0.85972(7) 0.0337(2) Uani 1 1 d . . . . .
C8 C 0.82266(6) 0.73276(18) 0.64621(7) 0.0349(2) Uani 1 1 d . . . . .
C9 C 0.92609(8) 0.7126(2) 0.57211(9) 0.0493(3) Uani 1 1 d . . . . .
H9 H 0.9756 0.7456 0.5534 0.059 Uiso 1 1 calc R . . . .
C10 C 0.86989(8) 0.5448(2) 0.54171(9) 0.0477(3) Uani 1 1 d . . . . .
H10 H 0.8731 0.4388 0.4979 0.057 Uiso 1 1 calc R . . . .
C11 C 0.93975(9) 1.0235(2) 0.68573(14) 0.0636(4) Uani 1 1 d . . . . .
H11A H 0.9225 1.1434 0.6418 0.095 Uiso 1 1 calc GR . . . .
H11B H 1.0042 1.0061 0.7069 0.095 Uiso 1 1 calc GR . . . .
H11C H 0.9211 1.0501 0.7408 0.095 Uiso 1 1 calc GR . . . .
C12 C 0.73306(8) 0.4057(2) 0.57665(10) 0.0492(3) Uani 1 1 d . . . . .
H12A H 0.7393 0.3426 0.6385 0.074 Uiso 1 1 calc GR . . . .
H12B H 0.7355 0.2940 0.5321 0.074 Uiso 1 1 calc GR . . . .
H12C H 0.6762 0.4796 0.5522 0.074 Uiso 1 1 calc GR . . . .
N1 N 0.77723(5) 0.65726(15) 0.79748(6) 0.0346(2) Uani 1 1 d . . . . .
N2 N 0.84670(7) 0.51509(18) 0.82198(8) 0.0465(3) Uani 1 1 d . . . . .
N3 N 0.84241(7) 0.4029(2) 0.89569(8) 0.0530(3) Uani 1 1 d . . . . .
N4 N 0.77136(7) 0.46667(18) 0.92101(7) 0.0463(3) Uani 1 1 d . . . . .
N5 N 0.89640(6) 0.82715(16) 0.63661(7) 0.0406(2) Uani 1 1 d . . . . .
N6 N 0.80640(6) 0.55892(16) 0.58761(7) 0.0386(2) 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
B1 C8 1.6077(16) . ?
B1 N1 1.5754(15) . ?
C1 C2 1.3921(16) . ?
C1 C6 1.3971(15) . ?
C1 C7 1.4690(14) . ?
C2 C3 1.3892(16) . ?
C3 C4 1.373(2) . ?
C4 C5 1.382(2) . ?
C5 C6 1.3829(17) . ?
C7 N1 1.3472(13) . ?
C7 N4 1.3340(14) . ?
C8 N5 1.3452(13) . ?
C8 N6 1.3458(15) . ?
C9 C10 1.338(2) . ?
C9 N5 1.3803(16) . ?
C10 N6 1.3784(14) . ?
C11 N5 1.4589(17) . ?
C12 N6 1.4583(15) . ?
N1 N2 1.3529(12) . ?
N2 N3 1.3035(15) . ?
N3 N4 1.3468(14) . ?

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
N1 B1 C8 108.62(9) . . ?
C2 C1 C6 118.65(10) . . ?
C2 C1 C7 122.50(9) . . ?
C6 C1 C7 118.84(10) . . ?
C3 C2 C1 120.18(11) . . ?
C4 C3 C2 120.65(12) . . ?
C3 C4 C5 119.71(11) . . ?
C4 C5 C6 120.34(12) . . ?
C5 C6 C1 120.46(13) . . ?
N1 C7 C1 127.66(9) . . ?
N4 C7 C1 123.10(9) . . ?
N4 C7 N1 109.24(9) . . ?
N5 C8 B1 128.03(10) . . ?
N5 C8 N6 105.49(9) . . ?
N6 C8 B1 126.39(9) . . ?
C10 C9 N5 106.85(10) . . ?
C9 C10 N6 107.02(11) . . ?
C7 N1 B1 132.84(9) . . ?
C7 N1 N2 106.72(9) . . ?
N2 N1 B1 120.43(9) . . ?
N3 N2 N1 107.79(9) . . ?
N2 N3 N4 110.38(10) . . ?
C7 N4 N3 105.88(9) . . ?
C8 N5 C9 110.34(10) . . ?
C8 N5 C11 125.88(10) . . ?
C9 N5 C11 123.78(11) . . ?
C8 N6 C10 110.31(10) . . ?
C8 N6 C12 124.35(9) . . ?
C10 N6 C12 125.33(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
