# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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. 
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data_mo_ljl_zb_230921_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2346317'
loop_
_audit_author_name
_audit_author_address
'Li Jun Long'
;Chengdu university
China
;
_audit_update_record             
;
2024-04-07 deposited with the CCDC.	2025-08-20 downloaded from the CCDC.
;
_audit_creation_date             2023-09-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 B N2 O3'
_chemical_formula_sum            'C22 H23 B N2 O3'
_chemical_formula_weight         374.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   28.670(12)
_cell_length_b                   7.613(3)
_cell_length_c                   17.786(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.54(2)
_cell_angle_gamma                90
_cell_volume                     3839(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3150
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.334
_cell_measurement_theta_min      2.316
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1211 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.9069.
The λ/2 correction factor is Not present.
;
_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    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15650
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_min         2.316
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2948
_reflns_number_total             4369
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.032
_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)+(0.0373P)²+3.8813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1347
_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 Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 B1(H1D,H1E)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C10(H10A,H10B,H10C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33176(5) 0.33035(18) 0.75071(7) 0.0285(3) Uani 1 1 d . . . . .
O2 O 0.43558(5) 0.42897(19) 0.77634(9) 0.0364(4) Uani 1 1 d . . . . .
O3 O 0.36499(5) 0.16088(18) 0.67433(8) 0.0329(4) Uani 1 1 d . . . . .
N1 N 0.33263(6) 0.8116(2) 0.50631(9) 0.0305(4) Uani 1 1 d . . . . .
N2 N 0.37076(6) 0.5955(2) 0.46895(9) 0.0275(4) Uani 1 1 d . . . . .
C1 C 0.54232(9) 1.1153(3) 0.93035(13) 0.0415(6) Uani 1 1 d . . . . .
H1A H 0.5499 1.0798 0.9837 0.062 Uiso 1 1 calc R U . . .
H1B H 0.5257 1.2282 0.9272 0.062 Uiso 1 1 calc R U . . .
H1C H 0.5715 1.1271 0.9084 0.062 Uiso 1 1 calc R U . . .
C2 C 0.51142(7) 0.9785(3) 0.88712(12) 0.0303(5) Uani 1 1 d . . . . .
C3 C 0.47447(7) 1.0273(3) 0.83113(12) 0.0299(5) Uani 1 1 d . . . . .
H3 H 0.4685 1.1483 0.8210 0.036 Uiso 1 1 calc R U . . .
C4 C 0.44610(7) 0.9013(3) 0.78966(11) 0.0262(4) Uani 1 1 d . . . . .
H4 H 0.4211 0.9371 0.7516 0.031 Uiso 1 1 calc R U . . .
C5 C 0.45438(7) 0.7240(3) 0.80394(10) 0.0225(4) Uani 1 1 d . . . . .
C6 C 0.42560(7) 0.5821(3) 0.76245(11) 0.0242(4) Uani 1 1 d . . . . .
C7 C 0.38098(7) 0.6239(3) 0.70555(10) 0.0225(4) Uani 1 1 d . . . . .
H7 H 0.3856 0.7340 0.6770 0.027 Uiso 1 1 calc R U . . .
C8 C 0.36861(7) 0.4705(3) 0.65008(10) 0.0241(4) Uani 1 1 d . . . . .
H8 H 0.3971 0.4441 0.6257 0.029 Uiso 1 1 calc R U . . .
C9 C 0.34188(7) 0.6407(3) 0.51943(10) 0.0233(4) Uani 1 1 d . . . . .
C10 C 0.30192(9) 0.9212(3) 0.54568(15) 0.0475(7) Uani 1 1 d . . . . .
H10A H 0.2718 0.9401 0.5125 0.071 Uiso 1 1 calc R U . . .
H10B H 0.3172 1.0347 0.5584 0.071 Uiso 1 1 calc R U . . .
H10C H 0.2962 0.8623 0.5924 0.071 Uiso 1 1 calc R U . . .
C11 C 0.37930(8) 0.7360(3) 0.42457(12) 0.0379(6) Uani 1 1 d . . . . .
H11 H 0.3983 0.7368 0.3851 0.045 Uiso 1 1 calc R U . . .
C12 C 0.35551(9) 0.8714(3) 0.44803(13) 0.0414(6) Uani 1 1 d . . . . .
H12 H 0.3545 0.9875 0.4283 0.050 Uiso 1 1 calc R U . . .
C13 C 0.35686(7) 0.3106(3) 0.69082(10) 0.0251(4) Uani 1 1 d . . . . .
C14 C 0.31954(7) 0.4965(3) 0.77345(10) 0.0247(4) Uani 1 1 d . . . . .
C15 C 0.28453(7) 0.5029(3) 0.81972(11) 0.0307(5) Uani 1 1 d . . . . .
H15 H 0.2706 0.3977 0.8347 0.037 Uiso 1 1 calc R U . . .
C16 C 0.27020(7) 0.6637(3) 0.84361(12) 0.0345(5) Uani 1 1 d . . . . .
H16 H 0.2465 0.6695 0.8755 0.041 Uiso 1 1 calc R U . . .
C17 C 0.29027(7) 0.8165(3) 0.82126(11) 0.0320(5) Uani 1 1 d . . . . .
H17 H 0.2798 0.9271 0.8370 0.038 Uiso 1 1 calc R U . . .
C18 C 0.32575(7) 0.8086(3) 0.77585(11) 0.0275(4) Uani 1 1 d . . . . .
H18 H 0.3394 0.9142 0.7608 0.033 Uiso 1 1 calc R U . . .
C19 C 0.34135(7) 0.6477(3) 0.75229(10) 0.0232(4) Uani 1 1 d . . . . .
C20 C 0.51986(7) 0.8006(3) 0.90052(11) 0.0313(5) Uani 1 1 d . . . . .
H20 H 0.5451 0.7652 0.9382 0.038 Uiso 1 1 calc R U . . .
C21 C 0.49200(7) 0.6745(3) 0.85976(11) 0.0281(5) Uani 1 1 d . . . . .
H21 H 0.4984 0.5536 0.8696 0.034 Uiso 1 1 calc R U . . .
C22 C 0.38851(9) 0.4188(3) 0.45915(13) 0.0410(6) Uani 1 1 d . . . . .
H22A H 0.3792 0.3414 0.4984 0.062 Uiso 1 1 calc R U . . .
H22B H 0.4230 0.4220 0.4637 0.062 Uiso 1 1 calc R U . . .
H22C H 0.3752 0.3743 0.4088 0.062 Uiso 1 1 calc R U . . .
B1 B 0.32393(9) 0.5127(3) 0.58096(12) 0.0284(5) Uani 1 1 d . . . . .
H1D H 0.3120 0.4016 0.5562 0.034 Uiso 1 1 calc R U . . .
H1E H 0.2978 0.5691 0.6026 0.034 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
O1 C13 1.379(2) . ?
O1 C14 1.389(2) . ?
O2 C6 1.217(2) . ?
O3 C13 1.208(2) . ?
N1 C9 1.341(3) . ?
N1 C10 1.465(3) . ?
N1 C12 1.383(3) . ?
N2 C9 1.353(2) . ?
N2 C11 1.373(3) . ?
N2 C22 1.457(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.503(3) . ?
C2 C3 1.392(3) . ?
C2 C20 1.390(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(3) . ?
C5 C6 1.487(3) . ?
C5 C21 1.404(3) . ?
C6 C7 1.542(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.536(3) . ?
C7 C19 1.515(3) . ?
C8 H8 1.0000 . ?
C8 C13 1.481(3) . ?
C8 B1 1.669(3) . ?
C9 B1 1.606(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.336(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.390(3) . ?
C14 C19 1.388(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.378(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(3) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
B1 H1D 0.9900 . ?
B1 H1E 0.9900 . ?

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
C13 O1 C14 120.49(15) . . ?
C9 N1 C10 125.94(19) . . ?
C9 N1 C12 110.23(18) . . ?
C12 N1 C10 123.8(2) . . ?
C9 N2 C11 111.22(18) . . ?
C9 N2 C22 124.98(18) . . ?
C11 N2 C22 123.71(19) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 120.6(2) . . ?
C20 C2 C1 120.9(2) . . ?
C20 C2 C3 118.48(19) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.08(19) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 123.27(17) . . ?
C4 C5 C21 118.85(18) . . ?
C21 C5 C6 117.88(18) . . ?
O2 C6 C5 119.91(18) . . ?
O2 C6 C7 118.55(18) . . ?
C5 C6 C7 121.42(17) . . ?
C6 C7 H7 110.3 . . ?
C8 C7 C6 110.78(16) . . ?
C8 C7 H7 110.3 . . ?
C19 C7 C6 106.35(15) . . ?
C19 C7 H7 110.3 . . ?
C19 C7 C8 108.86(16) . . ?
C7 C8 H8 107.8 . . ?
C7 C8 B1 113.93(16) . . ?
C13 C8 C7 110.99(15) . . ?
C13 C8 H8 107.8 . . ?
C13 C8 B1 108.22(16) . . ?
B1 C8 H8 107.8 . . ?
N1 C9 N2 104.85(17) . . ?
N1 C9 B1 129.20(18) . . ?
N2 C9 B1 125.94(18) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11 126.9 . . ?
C12 C11 N2 106.2(2) . . ?
C12 C11 H11 126.9 . . ?
N1 C12 H12 126.2 . . ?
C11 C12 N1 107.52(19) . . ?
C11 C12 H12 126.2 . . ?
O1 C13 C8 118.09(17) . . ?
O3 C13 O1 115.60(17) . . ?
O3 C13 C8 126.19(18) . . ?
O1 C14 C15 116.09(18) . . ?
C19 C14 O1 122.22(17) . . ?
C19 C14 C15 121.69(19) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.2(2) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C7 117.00(17) . . ?
C14 C19 C18 118.09(18) . . ?
C18 C19 C7 124.91(18) . . ?
C2 C20 H20 119.5 . . ?
C21 C20 C2 120.9(2) . . ?
C21 C20 H20 119.5 . . ?
C5 C21 H21 119.7 . . ?
C20 C21 C5 120.5(2) . . ?
C20 C21 H21 119.7 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C8 B1 H1D 109.8 . . ?
C8 B1 H1E 109.8 . . ?
C9 B1 C8 109.26(17) . . ?
C9 B1 H1D 109.8 . . ?
C9 B1 H1E 109.8 . . ?
H1D B1 H1E 108.3 . . ?

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
O1 C14 C15 C16 -179.15(18) . . . . ?
O1 C14 C19 C7 -2.6(3) . . . . ?
O1 C14 C19 C18 178.05(17) . . . . ?
O2 C6 C7 C8 -25.3(2) . . . . ?
O2 C6 C7 C19 92.8(2) . . . . ?
N1 C9 B1 C8 -107.2(2) . . . . ?
N2 C9 B1 C8 72.3(2) . . . . ?
N2 C11 C12 N1 -0.2(2) . . . . ?
C1 C2 C3 C4 178.8(2) . . . . ?
C1 C2 C20 C21 -178.8(2) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C20 C21 C5 -0.2(3) . . . . ?
C3 C2 C20 C21 -0.6(3) . . . . ?
C3 C4 C5 C6 179.73(18) . . . . ?
C3 C4 C5 C21 -0.9(3) . . . . ?
C4 C5 C6 O2 177.98(19) . . . . ?
C4 C5 C6 C7 -6.2(3) . . . . ?
C4 C5 C21 C20 0.9(3) . . . . ?
C5 C6 C7 C8 158.87(17) . . . . ?
C5 C6 C7 C19 -83.0(2) . . . . ?
C6 C5 C21 C20 -179.64(18) . . . . ?
C6 C7 C8 C13 63.4(2) . . . . ?
C6 C7 C8 B1 -174.13(16) . . . . ?
C6 C7 C19 C14 -82.4(2) . . . . ?
C6 C7 C19 C18 97.0(2) . . . . ?
C7 C8 C13 O1 37.8(2) . . . . ?
C7 C8 C13 O3 -146.3(2) . . . . ?
C7 C8 B1 C9 74.9(2) . . . . ?
C8 C7 C19 C14 37.0(2) . . . . ?
C8 C7 C19 C18 -143.62(18) . . . . ?
C9 N1 C12 C11 0.0(2) . . . . ?
C9 N2 C11 C12 0.3(2) . . . . ?
C10 N1 C9 N2 178.66(18) . . . . ?
C10 N1 C9 B1 -1.8(3) . . . . ?
C10 N1 C12 C11 -178.53(19) . . . . ?
C11 N2 C9 N1 -0.3(2) . . . . ?
C11 N2 C9 B1 -179.88(18) . . . . ?
C12 N1 C9 N2 0.2(2) . . . . ?
C12 N1 C9 B1 179.75(19) . . . . ?
C13 O1 C14 C15 163.79(17) . . . . ?
C13 O1 C14 C19 -17.1(3) . . . . ?
C13 C8 B1 C9 -161.09(17) . . . . ?
C14 O1 C13 O3 -178.59(17) . . . . ?
C14 O1 C13 C8 -2.3(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C14 C19 C7 176.52(17) . . . . ?
C15 C14 C19 C18 -2.9(3) . . . . ?
C15 C16 C17 C18 -1.4(3) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C7 -177.42(17) . . . . ?
C17 C18 C19 C14 1.9(3) . . . . ?
C19 C7 C8 C13 -53.2(2) . . . . ?
C19 C7 C8 B1 69.3(2) . . . . ?
C19 C14 C15 C16 1.7(3) . . . . ?
C20 C2 C3 C4 0.6(3) . . . . ?
C21 C5 C6 O2 -1.4(3) . . . . ?
C21 C5 C6 C7 174.35(17) . . . . ?
C22 N2 C9 N1 -176.85(18) . . . . ?
C22 N2 C9 B1 3.5(3) . . . . ?
C22 N2 C11 C12 176.9(2) . . . . ?
B1 C8 C13 O1 -87.9(2) . . . . ?
B1 C8 C13 O3 88.0(2) . . . . ?

_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_mo_ljl_zb_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2393912'
loop_
_audit_author_name
_audit_author_address
'Xiang Zhang'
;School of Pharmacy, Chengdu University
China
;
_audit_update_record             
;
2024-10-25 deposited with the CCDC.	2025-08-20 downloaded from the CCDC.
;
_audit_creation_date             2024-10-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H27 B N2 O4'
_chemical_formula_sum            'C23 H26 B N2 O4'
_chemical_formula_weight         405.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.3194(5)
_cell_length_b                   16.4785(8)
_cell_length_c                   14.8376(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.632(2)
_cell_angle_gamma                90
_cell_volume                     2231.81(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7610
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      26.870
_cell_measurement_theta_min      2.231
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0878 before and 0.0607 after correction.
The Ratio of minimum to maximum transmission is 0.8930.
The λ/2 correction factor is Not present.
;
_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    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             860
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            37385
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         2.231
_diffrn_ambient_temperature      270.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3401
_reflns_number_total             5127
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0091(14)
_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   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         5127
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.061
_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)+(0.0651P)²+0.3001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1389
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 B1(H1D,H1E)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C24(H24A,H24B,H24C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56465(14) 0.37301(8) 0.80266(8) 0.0569(4) Uani 1 1 d . . . . .
O2 O 0.80192(15) 0.20923(8) 0.58046(8) 0.0549(4) Uani 1 1 d . . . . .
H2 H 0.8226 0.1788 0.5412 0.082 Uiso 1 1 calc R U . . .
O3 O 0.88903(15) 0.42969(8) 0.81007(7) 0.0561(4) Uani 1 1 d . . . . .
O4 O 0.88173(13) 0.38656(7) 0.95091(7) 0.0490(3) Uani 1 1 d . . . . .
N1 N 1.06361(16) 0.21054(9) 1.00074(10) 0.0491(4) Uani 1 1 d . . . . .
C1 C 1.2697(3) 0.34921(18) 0.8950(2) 0.1025(10) Uani 1 1 d . . . . .
H1A H 1.1950 0.3759 0.8510 0.154 Uiso 1 1 calc R U . . .
H1B H 1.3306 0.3177 0.8633 0.154 Uiso 1 1 calc R U . . .
H1C H 1.3284 0.3891 0.9328 0.154 Uiso 1 1 calc R U . . .
N2 N 1.20152(16) 0.29589(10) 0.95290(11) 0.0545(4) Uani 1 1 d . . . . .
C3 C 1.08559(17) 0.24778(11) 0.92415(11) 0.0428(4) Uani 1 1 d . . . . .
C4 C 0.82713(17) 0.29172(10) 0.82607(10) 0.0386(4) Uani 1 1 d . . . . .
H4 H 0.7754 0.2613 0.8665 0.046 Uiso 1 1 calc R U . . .
C5 C 0.72592(17) 0.29539(9) 0.73051(9) 0.0359(3) Uani 1 1 d . . . . .
H5 H 0.7821 0.3163 0.6863 0.043 Uiso 1 1 calc R U . . .
C6 C 0.59540(17) 0.35141(10) 0.73031(10) 0.0386(4) Uani 1 1 d . . . . .
C7 C 0.50363(17) 0.37884(10) 0.64134(10) 0.0378(4) Uani 1 1 d . . . . .
C8 C 0.52937(18) 0.35573(11) 0.55613(11) 0.0449(4) Uani 1 1 d . . . . .
H8 H 0.6077 0.3217 0.5527 0.054 Uiso 1 1 calc R U . . .
C9 C 0.4394(2) 0.38289(12) 0.47637(11) 0.0508(5) Uani 1 1 d . . . . .
H9 H 0.4575 0.3660 0.4199 0.061 Uiso 1 1 calc R U . . .
C10 C 0.32328(19) 0.43442(11) 0.47823(12) 0.0483(4) Uani 1 1 d . . . . .
C11 C 0.2261(2) 0.46290(14) 0.39058(13) 0.0636(6) Uani 1 1 d . . . . .
H11A H 0.2829 0.4939 0.3556 0.095 Uiso 1 1 calc R U . . .
H11B H 0.1492 0.4962 0.4049 0.095 Uiso 1 1 calc R U . . .
H11C H 0.1842 0.4168 0.3553 0.095 Uiso 1 1 calc R U . . .
C12 C 0.9545(2) 0.14817(13) 1.00298(18) 0.0737(6) Uani 1 1 d . . . . .
H12A H 0.9150 0.1302 0.9414 0.110 Uiso 1 1 calc R U . . .
H12B H 0.8772 0.1699 1.0298 0.110 Uiso 1 1 calc R U . . .
H12C H 0.9992 0.1032 1.0392 0.110 Uiso 1 1 calc R U . . .
C13 C 1.1633(3) 0.23682(15) 1.07582(13) 0.0658(6) Uani 1 1 d . . . . .
H13 H 1.1690 0.2205 1.1364 0.079 Uiso 1 1 calc R U . . .
C14 C 1.2492(2) 0.28927(14) 1.04639(14) 0.0682(6) Uani 1 1 d . . . . .
H14 H 1.3277 0.3168 1.0821 0.082 Uiso 1 1 calc R U . . .
C15 C 0.38698(18) 0.43043(10) 0.64369(11) 0.0457(4) Uani 1 1 d . . . . .
H15 H 0.3674 0.4466 0.7001 0.055 Uiso 1 1 calc R U . . .
C16 C 0.29974(19) 0.45804(11) 0.56349(12) 0.0500(4) Uani 1 1 d . . . . .
H16 H 0.2232 0.4934 0.5667 0.060 Uiso 1 1 calc R U . . .
C17 C 0.66643(17) 0.21190(9) 0.69857(10) 0.0362(4) Uani 1 1 d . . . . .
C18 C 0.70639(18) 0.17144(10) 0.62469(10) 0.0411(4) Uani 1 1 d . . . . .
C19 C 0.6476(2) 0.09614(11) 0.59712(12) 0.0490(4) Uani 1 1 d . . . . .
H19 H 0.6742 0.0700 0.5474 0.059 Uiso 1 1 calc R U . . .
C20 C 0.5502(2) 0.05961(11) 0.64265(13) 0.0533(5) Uani 1 1 d . . . . .
H20 H 0.5118 0.0088 0.6240 0.064 Uiso 1 1 calc R U . . .
C21 C 0.5097(2) 0.09826(12) 0.71586(12) 0.0525(5) Uani 1 1 d . . . . .
H21 H 0.4442 0.0738 0.7471 0.063 Uiso 1 1 calc R U . . .
C22 C 0.56710(18) 0.17352(11) 0.74248(11) 0.0436(4) Uani 1 1 d . . . . .
H22 H 0.5383 0.1995 0.7916 0.052 Uiso 1 1 calc R U . . .
C23 C 0.86411(17) 0.37260(10) 0.86879(10) 0.0400(4) Uani 1 1 d . . . . .
C24 C 0.9326(3) 0.50835(13) 0.84934(14) 0.0794(7) Uani 1 1 d . . . . .
H24A H 0.8543 0.5311 0.8745 0.119 Uiso 1 1 calc R U . . .
H24B H 0.9543 0.5436 0.8023 0.119 Uiso 1 1 calc R U . . .
H24C H 1.0181 0.5026 0.8973 0.119 Uiso 1 1 calc R U . . .
B1 B 0.9826(2) 0.24262(15) 0.82419(14) 0.0539(5) Uani 1 1 d . . . . .
H1D H 0.9620 0.1863 0.8073 0.065 Uiso 1 1 calc R U . . .
H1E H 1.0315 0.2671 0.7790 0.065 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
O1 C6 1.2188(18) . ?
O2 H2 0.8200 . ?
O2 C18 1.3589(19) . ?
O3 C23 1.3340(19) . ?
O3 C24 1.445(2) . ?
O4 C23 1.2182(17) . ?
N1 C3 1.343(2) . ?
N1 C12 1.451(3) . ?
N1 C13 1.369(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 N2 1.460(3) . ?
N2 C3 1.339(2) . ?
N2 C14 1.373(3) . ?
C3 B1 1.598(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.538(2) . ?
C4 C23 1.486(2) . ?
C4 B1 1.665(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.527(2) . ?
C5 C17 1.523(2) . ?
C6 C7 1.491(2) . ?
C7 C8 1.387(2) . ?
C7 C15 1.386(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(3) . ?
C10 C11 1.502(2) . ?
C10 C16 1.383(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.312(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.376(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.396(2) . ?
C17 C22 1.387(2) . ?
C18 C19 1.385(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.375(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.376(3) . ?
C22 H22 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
B1 H1D 0.9700 . ?
B1 H1E 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
C18 O2 H2 109.5 . . ?
C23 O3 C24 116.17(13) . . ?
C3 N1 C12 124.77(16) . . ?
C3 N1 C13 110.47(17) . . ?
C13 N1 C12 124.68(18) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
C3 N2 C1 126.00(18) . . ?
C3 N2 C14 110.55(17) . . ?
C14 N2 C1 123.4(2) . . ?
N1 C3 B1 126.55(16) . . ?
N2 C3 N1 104.60(14) . . ?
N2 C3 B1 128.48(17) . . ?
C5 C4 H4 107.4 . . ?
C5 C4 B1 112.20(12) . . ?
C23 C4 H4 107.4 . . ?
C23 C4 C5 113.85(13) . . ?
C23 C4 B1 108.37(14) . . ?
B1 C4 H4 107.4 . . ?
C4 C5 H5 108.6 . . ?
C6 C5 C4 111.47(12) . . ?
C6 C5 H5 108.6 . . ?
C17 C5 C4 111.63(12) . . ?
C17 C5 H5 108.6 . . ?
C17 C5 C6 107.81(12) . . ?
O1 C6 C5 120.24(14) . . ?
O1 C6 C7 119.77(15) . . ?
C7 C6 C5 119.98(13) . . ?
C8 C7 C6 123.37(15) . . ?
C15 C7 C6 118.46(14) . . ?
C15 C7 C8 118.17(15) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.39(16) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.1 . . ?
C8 C9 C10 121.72(16) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C11 120.87(17) . . ?
C9 C10 C16 117.46(15) . . ?
C16 C10 C11 121.67(18) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 H13 126.4 . . ?
C14 C13 N1 107.29(18) . . ?
C14 C13 H13 126.4 . . ?
N2 C14 H14 126.5 . . ?
C13 C14 N2 107.08(18) . . ?
C13 C14 H14 126.5 . . ?
C7 C15 H15 119.6 . . ?
C16 C15 C7 120.71(16) . . ?
C16 C15 H15 119.6 . . ?
C10 C16 H16 119.2 . . ?
C15 C16 C10 121.53(17) . . ?
C15 C16 H16 119.2 . . ?
C18 C17 C5 122.53(14) . . ?
C22 C17 C5 120.08(14) . . ?
C22 C17 C18 117.39(15) . . ?
O2 C18 C17 117.70(14) . . ?
O2 C18 C19 121.78(15) . . ?
C19 C18 C17 120.51(15) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.55(17) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.91(17) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.41(17) . . ?
C22 C21 H21 120.3 . . ?
C17 C22 H22 118.9 . . ?
C21 C22 C17 122.23(16) . . ?
C21 C22 H22 118.9 . . ?
O3 C23 C4 114.20(13) . . ?
O4 C23 O3 120.92(15) . . ?
O4 C23 C4 124.67(14) . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C3 B1 C4 108.68(14) . . ?
C3 B1 H1D 110.0 . . ?
C3 B1 H1E 110.0 . . ?
C4 B1 H1D 110.0 . . ?
C4 B1 H1E 110.0 . . ?
H1D B1 H1E 108.3 . . ?

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
O1 C6 C7 C8 -178.66(16) . . . . ?
O1 C6 C7 C15 1.7(2) . . . . ?
O2 C18 C19 C20 -179.44(16) . . . . ?
N1 C3 B1 C4 69.6(2) . . . . ?
N1 C13 C14 N2 0.5(2) . . . . ?
C1 N2 C3 N1 179.6(2) . . . . ?
C1 N2 C3 B1 -7.1(3) . . . . ?
C1 N2 C14 C13 179.7(2) . . . . ?
N2 C3 B1 C4 -102.2(2) . . . . ?
C3 N1 C13 C14 -1.1(2) . . . . ?
C3 N2 C14 C13 0.2(2) . . . . ?
C4 C5 C6 O1 -15.3(2) . . . . ?
C4 C5 C6 C7 165.71(14) . . . . ?
C4 C5 C17 C18 -112.18(16) . . . . ?
C4 C5 C17 C22 68.68(18) . . . . ?
C5 C4 C23 O3 -39.85(19) . . . . ?
C5 C4 C23 O4 145.35(16) . . . . ?
C5 C4 B1 C3 175.66(15) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C5 C6 C7 C15 -179.28(14) . . . . ?
C5 C17 C18 O2 -0.2(2) . . . . ?
C5 C17 C18 C19 -178.93(15) . . . . ?
C5 C17 C22 C21 179.69(15) . . . . ?
C6 C5 C17 C18 125.08(15) . . . . ?
C6 C5 C17 C22 -54.06(18) . . . . ?
C6 C7 C8 C9 179.52(16) . . . . ?
C6 C7 C15 C16 179.42(16) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C7 C15 C16 C10 1.2(3) . . . . ?
C8 C7 C15 C16 -0.2(2) . . . . ?
C8 C9 C10 C11 -179.65(17) . . . . ?
C8 C9 C10 C16 -0.1(3) . . . . ?
C9 C10 C16 C15 -1.0(3) . . . . ?
C11 C10 C16 C15 178.55(17) . . . . ?
C12 N1 C3 N2 -175.85(16) . . . . ?
C12 N1 C3 B1 10.7(3) . . . . ?
C12 N1 C13 C14 175.94(18) . . . . ?
C13 N1 C3 N2 1.20(19) . . . . ?
C13 N1 C3 B1 -172.23(17) . . . . ?
C14 N2 C3 N1 -0.9(2) . . . . ?
C14 N2 C3 B1 172.40(17) . . . . ?
C15 C7 C8 C9 -0.8(3) . . . . ?
C17 C5 C6 O1 107.58(17) . . . . ?
C17 C5 C6 C7 -71.45(17) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
C18 C17 C22 C21 0.5(2) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C17 -0.7(3) . . . . ?
C22 C17 C18 O2 179.01(14) . . . . ?
C22 C17 C18 C19 0.2(2) . . . . ?
C23 C4 C5 C6 -47.66(18) . . . . ?
C23 C4 C5 C17 -168.28(13) . . . . ?
C23 C4 B1 C3 49.1(2) . . . . ?
C24 O3 C23 O4 -2.0(3) . . . . ?
C24 O3 C23 C4 -177.01(17) . . . . ?
B1 C4 C5 C6 -171.20(15) . . . . ?
B1 C4 C5 C17 68.18(18) . . . . ?
B1 C4 C23 O3 85.75(17) . . . . ?
B1 C4 C23 O4 -89.1(2) . . . . ?

_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_mo_ljl_zb_20240522r_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2374308'
loop_
_audit_author_name
_audit_author_address
'Li Jun Long'
;Chengdu university
China
;
_audit_update_record             
;
2024-07-29 deposited with the CCDC.	2025-08-20 downloaded from the CCDC.
;
_audit_creation_date             2024-05-22
_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         'C27 H29 B N2 O3'
_chemical_formula_sum            'C27 H29 B N2 O3'
_chemical_formula_weight         440.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.3606(12)
_cell_length_b                   10.7025(10)
_cell_length_c                   12.3148(14)
_cell_angle_alpha                73.538(4)
_cell_angle_beta                 84.906(4)
_cell_angle_gamma                64.683(3)
_cell_volume                     1182.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7750
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.466
_cell_measurement_theta_min      2.727
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7409
_exptl_absorpt_correction_T_min  0.6367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1733 before and 0.0977 after correction.
The Ratio of minimum to maximum transmission is 0.8594.
The λ/2 correction factor is Not present.
;
_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    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27388
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.615
_diffrn_reflns_theta_min         2.176
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_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           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3876
_reflns_number_total             5417
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²+0.2480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1481
_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 Ternary CH refined with riding coordinates:
 C7(H7), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 B1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C14(H14), C15(H15),
 C18(H18), C19(H19), C24(H24), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,
 H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.18771(12) 0.81536(13) 0.67554(10) 0.0408(3) Uani 1 1 d . . . . .
O2 O 0.19515(14) 0.52421(15) 0.85314(11) 0.0509(4) Uani 1 1 d . . . . .
O3 O 0.26247(13) 0.45820(14) 0.69232(10) 0.0452(3) Uani 1 1 d . . . . .
N1 N 0.67169(15) 0.32494(16) 0.63376(12) 0.0415(4) Uani 1 1 d . . . . .
N2 N 0.58364(15) 0.18007(15) 0.72624(13) 0.0430(4) Uani 1 1 d . . . . .
C1 C 0.9032(2) 0.8256(2) 0.57109(19) 0.0517(5) Uani 1 1 d . . . . .
H1 H 0.987451 0.839318 0.549110 0.062 Uiso 1 1 calc R U . . .
C2 C 0.88504(18) 0.7710(2) 0.68181(18) 0.0471(5) Uani 1 1 d . . . . .
H2 H 0.957172 0.746351 0.736530 0.057 Uiso 1 1 calc R U . . .
C3 C 0.75984(17) 0.74982(17) 0.71752(15) 0.0372(4) Uani 1 1 d . . . . .
C4 C 0.73752(18) 0.68980(19) 0.83161(15) 0.0411(4) Uani 1 1 d . . . . .
H4 H 0.807602 0.663869 0.888479 0.049 Uiso 1 1 calc R U . . .
C5 C 0.61695(18) 0.66852(18) 0.86138(14) 0.0377(4) Uani 1 1 d . . . . .
H5 H 0.605191 0.626547 0.938471 0.045 Uiso 1 1 calc R U . . .
C6 C 0.50924(16) 0.70789(16) 0.77943(13) 0.0310(3) Uani 1 1 d . . . . .
C7 C 0.38238(16) 0.66931(16) 0.81016(13) 0.0301(3) Uani 1 1 d . . . . .
H7 H 0.378713 0.637143 0.894492 0.036 Uiso 1 1 calc R U . . .
C8 C 0.24481(16) 0.80231(17) 0.76306(13) 0.0308(3) Uani 1 1 d . . . . .
C9 C 0.18155(17) 0.91909(17) 0.82096(13) 0.0322(3) Uani 1 1 d . . . . .
C10 C 0.04635(18) 1.02784(18) 0.78482(15) 0.0394(4) Uani 1 1 d . . . . .
H10 H -0.003815 1.025133 0.725204 0.047 Uiso 1 1 calc R U . . .
C11 C -0.01569(19) 1.13948(19) 0.83449(16) 0.0433(4) Uani 1 1 d . . . . .
H11 H -0.108484 1.211856 0.808826 0.052 Uiso 1 1 calc R U . . .
C12 C 0.05383(19) 1.14865(18) 0.92070(15) 0.0402(4) Uani 1 1 d . . . . .
C13 C -0.0135(2) 1.2725(2) 0.97322(19) 0.0565(5) Uani 1 1 d . . . . .
H13A H 0.002176 1.236132 1.055687 0.085 Uiso 1 1 calc R U . . .
H13B H -0.116309 1.321558 0.954522 0.085 Uiso 1 1 calc R U . . .
H13C H 0.029974 1.340142 0.943564 0.085 Uiso 1 1 calc R U . . .
C14 C 0.25039(19) 0.92589(19) 0.90943(15) 0.0426(4) Uani 1 1 d . . . . .
H14 H 0.341602 0.851751 0.937341 0.051 Uiso 1 1 calc R U . . .
C15 C 0.1874(2) 1.0396(2) 0.95731(16) 0.0479(5) Uani 1 1 d . . . . .
H15 H 0.237221 1.042830 1.016875 0.057 Uiso 1 1 calc R U . . .
C16 C 0.40199(16) 0.54586(16) 0.76007(13) 0.0313(3) Uani 1 1 d . . . . .
H16 H 0.415457 0.576432 0.676867 0.038 Uiso 1 1 calc R U . . .
C17 C 0.59837(17) 0.29886(17) 0.72730(14) 0.0358(4) Uani 1 1 d . . . . .
C18 C 0.7020(2) 0.2252(2) 0.57538(17) 0.0536(5) Uani 1 1 d . . . . .
H18 H 0.752227 0.221319 0.507138 0.064 Uiso 1 1 calc R U . . .
C19 C 0.6478(2) 0.1351(2) 0.63240(18) 0.0535(5) Uani 1 1 d . . . . .
H19 H 0.652066 0.053927 0.612471 0.064 Uiso 1 1 calc R U . . .
C20 C 0.5073(2) 0.1116(2) 0.8067(2) 0.0641(6) Uani 1 1 d . . . . .
H20A H 0.483366 0.152700 0.871399 0.096 Uiso 1 1 calc R U . . .
H20B H 0.567455 0.008233 0.833066 0.096 Uiso 1 1 calc R U . . .
H20C H 0.419268 0.127432 0.770136 0.096 Uiso 1 1 calc R U . . .
C21 C 0.7150(2) 0.4430(2) 0.5993(2) 0.0631(6) Uani 1 1 d . . . . .
H21A H 0.647915 0.521292 0.540228 0.095 Uiso 1 1 calc R U . . .
H21B H 0.811291 0.409276 0.569700 0.095 Uiso 1 1 calc R U . . .
H21C H 0.714918 0.477906 0.664812 0.095 Uiso 1 1 calc R U . . .
C22 C 0.27526(17) 0.51306(17) 0.77577(14) 0.0352(4) Uani 1 1 d . . . . .
C23 C 0.1514(2) 0.4098(2) 0.7025(2) 0.0605(6) Uani 1 1 d . . . . .
H23A H 0.168763 0.331296 0.771910 0.091 Uiso 1 1 calc R U . . .
H23B H 0.150514 0.375675 0.636796 0.091 Uiso 1 1 calc R U . . .
H23C H 0.058916 0.489526 0.705762 0.091 Uiso 1 1 calc R U . . .
C24 C 0.52669(16) 0.77028(16) 0.66937(13) 0.0319(3) Uani 1 1 d . . . . .
H24 H 0.452585 0.801204 0.614576 0.038 Uiso 1 1 calc R U . . .
C25 C 0.65245(16) 0.79029(16) 0.63444(14) 0.0327(3) Uani 1 1 d . . . . .
C26 C 0.67540(19) 0.84567(18) 0.51983(15) 0.0395(4) Uani 1 1 d . . . . .
H26 H 0.604553 0.871930 0.463496 0.047 Uiso 1 1 calc R U . . .
C27 C 0.7989(2) 0.8621(2) 0.48875(17) 0.0474(5) Uani 1 1 d . . . . .
H27 H 0.813642 0.898258 0.411103 0.057 Uiso 1 1 calc R U . . .
B1 B 0.5425(2) 0.3932(2) 0.81593(16) 0.0377(4) Uani 1 1 d . . . . .
H1A H 0.619856 0.414809 0.835821 0.045 Uiso 1 1 calc R U . . .
H1B H 0.515433 0.338497 0.886136 0.045 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
O1 C8 1.2201(18) . ?
O2 C22 1.2042(19) . ?
O3 C22 1.361(2) . ?
O3 C23 1.434(2) . ?
N1 C17 1.351(2) . ?
N1 C18 1.365(2) . ?
N1 C21 1.458(3) . ?
N2 C17 1.347(2) . ?
N2 C19 1.383(2) . ?
N2 C20 1.446(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.354(3) . ?
C1 C27 1.399(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.421(2) . ?
C3 C4 1.414(2) . ?
C3 C25 1.418(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.364(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.414(2) . ?
C6 C7 1.526(2) . ?
C6 C24 1.365(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.529(2) . ?
C7 C16 1.542(2) . ?
C8 C9 1.490(2) . ?
C9 C10 1.392(2) . ?
C9 C14 1.389(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(3) . ?
C12 C13 1.509(2) . ?
C12 C15 1.383(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C15 1.383(2) . ?
C15 H15 0.9500 . ?
C16 H16 1.0000 . ?
C16 C22 1.482(2) . ?
C16 B1 1.664(2) . ?
C17 B1 1.600(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.322(3) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24 0.9500 . ?
C24 C25 1.420(2) . ?
C25 C26 1.409(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.371(2) . ?
C27 H27 0.9500 . ?
B1 H1A 0.9900 . ?
B1 H1B 0.9900 . ?

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
C22 O3 C23 116.79(14) . . ?
C17 N1 C18 111.32(16) . . ?
C17 N1 C21 124.85(15) . . ?
C18 N1 C21 123.82(17) . . ?
C17 N2 C19 109.72(16) . . ?
C17 N2 C20 126.21(16) . . ?
C19 N2 C20 124.01(17) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C27 120.59(17) . . ?
C27 C1 H1 119.7 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.08(17) . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 123.22(16) . . ?
C4 C3 C25 118.44(15) . . ?
C25 C3 C2 118.33(16) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.07(15) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.10(16) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 121.11(14) . . ?
C24 C6 C5 118.71(15) . . ?
C24 C6 C7 119.93(14) . . ?
C6 C7 H7 109.3 . . ?
C6 C7 C8 108.96(12) . . ?
C6 C7 C16 108.88(12) . . ?
C8 C7 H7 109.3 . . ?
C8 C7 C16 111.07(12) . . ?
C16 C7 H7 109.3 . . ?
O1 C8 C7 119.94(14) . . ?
O1 C8 C9 119.30(14) . . ?
C9 C8 C7 120.74(13) . . ?
C10 C9 C8 118.67(14) . . ?
C14 C9 C8 123.53(15) . . ?
C14 C9 C10 117.80(15) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.81(16) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.63(16) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C13 121.37(17) . . ?
C11 C12 C15 117.42(16) . . ?
C15 C12 C13 121.21(17) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14 119.7 . . ?
C15 C14 C9 120.62(16) . . ?
C15 C14 H14 119.7 . . ?
C12 C15 C14 121.70(17) . . ?
C12 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C7 C16 H16 108.1 . . ?
C7 C16 B1 113.56(13) . . ?
C22 C16 C7 111.94(12) . . ?
C22 C16 H16 108.1 . . ?
C22 C16 B1 106.99(13) . . ?
B1 C16 H16 108.1 . . ?
N1 C17 B1 125.87(15) . . ?
N2 C17 N1 104.58(14) . . ?
N2 C17 B1 129.55(16) . . ?
N1 C18 H18 126.7 . . ?
C19 C18 N1 106.57(17) . . ?
C19 C18 H18 126.7 . . ?
N2 C19 H19 126.1 . . ?
C18 C19 N2 107.81(17) . . ?
C18 C19 H19 126.1 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 O3 121.93(15) . . ?
O2 C22 C16 127.09(15) . . ?
O3 C22 C16 110.88(13) . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C6 C24 H24 119.1 . . ?
C6 C24 C25 121.87(14) . . ?
C25 C24 H24 119.1 . . ?
C3 C25 C24 118.74(15) . . ?
C26 C25 C3 119.06(15) . . ?
C26 C25 C24 122.18(15) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 C25 120.72(17) . . ?
C27 C26 H26 119.6 . . ?
C1 C27 H27 119.9 . . ?
C26 C27 C1 120.17(18) . . ?
C26 C27 H27 119.9 . . ?
C16 B1 H1A 109.7 . . ?
C16 B1 H1B 109.7 . . ?
C17 B1 C16 110.01(13) . . ?
C17 B1 H1A 109.7 . . ?
C17 B1 H1B 109.7 . . ?
H1A B1 H1B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C8 C9 C10 11.0(2) . . . . ?
O1 C8 C9 C14 -168.89(16) . . . . ?
N1 C17 B1 C16 74.3(2) . . . . ?
N1 C18 C19 N2 0.1(2) . . . . ?
N2 C17 B1 C16 -104.95(19) . . . . ?
C1 C2 C3 C4 178.34(17) . . . . ?
C1 C2 C3 C25 -1.3(3) . . . . ?
C2 C1 C27 C26 1.4(3) . . . . ?
C2 C3 C4 C5 -178.45(16) . . . . ?
C2 C3 C25 C24 -179.67(15) . . . . ?
C2 C3 C25 C26 1.9(2) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C3 C25 C26 C27 -0.8(2) . . . . ?
C4 C3 C25 C24 0.6(2) . . . . ?
C4 C3 C25 C26 -177.83(15) . . . . ?
C4 C5 C6 C7 173.19(15) . . . . ?
C4 C5 C6 C24 -1.1(2) . . . . ?
C5 C6 C7 C8 132.65(15) . . . . ?
C5 C6 C7 C16 -106.08(16) . . . . ?
C5 C6 C24 C25 3.0(2) . . . . ?
C6 C7 C8 O1 100.69(16) . . . . ?
C6 C7 C8 C9 -77.38(17) . . . . ?
C6 C7 C16 C22 -173.80(13) . . . . ?
C6 C7 C16 B1 64.92(16) . . . . ?
C6 C24 C25 C3 -2.8(2) . . . . ?
C6 C24 C25 C26 175.61(15) . . . . ?
C7 C6 C24 C25 -171.33(14) . . . . ?
C7 C8 C9 C10 -170.96(14) . . . . ?
C7 C8 C9 C14 9.2(2) . . . . ?
C7 C16 C22 O2 -31.8(2) . . . . ?
C7 C16 C22 O3 151.87(13) . . . . ?
C7 C16 B1 C17 -153.86(14) . . . . ?
C8 C7 C16 C22 -53.82(17) . . . . ?
C8 C7 C16 B1 -175.10(13) . . . . ?
C8 C9 C10 C11 -178.93(15) . . . . ?
C8 C9 C14 C15 178.08(16) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C9 C14 C15 C12 1.1(3) . . . . ?
C10 C9 C14 C15 -1.8(3) . . . . ?
C10 C11 C12 C13 178.86(17) . . . . ?
C10 C11 C12 C15 -1.4(3) . . . . ?
C11 C12 C15 C14 0.5(3) . . . . ?
C13 C12 C15 C14 -179.72(18) . . . . ?
C14 C9 C10 C11 0.9(3) . . . . ?
C16 C7 C8 O1 -19.24(19) . . . . ?
C16 C7 C8 C9 162.69(13) . . . . ?
C17 N1 C18 C19 -0.1(2) . . . . ?
C17 N2 C19 C18 0.0(2) . . . . ?
C18 N1 C17 N2 0.10(19) . . . . ?
C18 N1 C17 B1 -179.27(16) . . . . ?
C19 N2 C17 N1 -0.05(18) . . . . ?
C19 N2 C17 B1 179.29(16) . . . . ?
C20 N2 C17 N1 -177.32(17) . . . . ?
C20 N2 C17 B1 2.0(3) . . . . ?
C20 N2 C19 C18 177.32(18) . . . . ?
C21 N1 C17 N2 -179.24(17) . . . . ?
C21 N1 C17 B1 1.4(3) . . . . ?
C21 N1 C18 C19 179.23(18) . . . . ?
C22 C16 B1 C17 82.13(16) . . . . ?
C23 O3 C22 O2 -1.9(2) . . . . ?
C23 O3 C22 C16 174.71(15) . . . . ?
C24 C6 C7 C8 -53.14(18) . . . . ?
C24 C6 C7 C16 68.14(17) . . . . ?
C24 C25 C26 C27 -179.20(16) . . . . ?
C25 C3 C4 C5 1.2(2) . . . . ?
C25 C26 C27 C1 -0.9(3) . . . . ?
C27 C1 C2 C3 -0.3(3) . . . . ?
B1 C16 C22 O2 93.2(2) . . . . ?
B1 C16 C22 O3 -83.13(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
