# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_230323lu_ngy_j_3_2_3_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2290532'
loop_
_audit_author_name
_audit_author_address
'Yuanyuan An'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-08-24 deposited with the CCDC.	2023-11-12 downloaded from the CCDC.
;
_audit_creation_date             2023-03-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 B N4 O2'
_chemical_formula_sum            'C22 H23 B N4 O2'
_chemical_formula_weight         386.25
_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                   9.5689(4)
_cell_length_b                   9.6362(4)
_cell_length_c                   10.9620(5)
_cell_angle_alpha                97.085(2)
_cell_angle_beta                 90.019(2)
_cell_angle_gamma                93.134(2)
_cell_volume                     1001.54(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3398
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.350
_cell_measurement_theta_min      2.659
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0948 before and 0.0433 after correction.
The Ratio of minimum to maximum transmission is 0.8919.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9586
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.581
_diffrn_reflns_theta_min         1.872
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_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                3412
_reflns_number_total             4593
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4593
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_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)+(0.0460P)²+0.3169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1221
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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
O1 O 0.16284(12) 0.22863(12) 0.60051(10) 0.0374(3) Uani 1 1 d . . . . .
O2 O 0.13583(13) 0.45617(14) 0.57619(11) 0.0453(3) Uani 1 1 d . . . . .
N1 N 0.29311(14) 0.32575(13) 0.46279(12) 0.0308(3) Uani 1 1 d . . . . .
N2 N 0.21957(16) 0.00448(17) 0.31106(17) 0.0542(5) Uani 1 1 d . . . . .
N3 N 0.74859(14) 0.18691(14) 0.10328(13) 0.0332(3) Uani 1 1 d . . . . .
N4 N 0.84267(13) 0.18012(13) 0.27953(13) 0.0323(3) Uani 1 1 d . . . . .
C1 C 0.18899(18) 0.17433(18) 0.87810(17) 0.0402(4) Uani 1 1 d . . . . .
H1 H 0.188231 0.081077 0.838027 0.048 Uiso 1 1 calc R U . . .
C2 C 0.25233(19) 0.2062(2) 0.99188(18) 0.0460(5) Uani 1 1 d . . . . .
H2 H 0.294975 0.135448 1.029690 0.055 Uiso 1 1 calc R U . . .
C3 C 0.25330(19) 0.3407(2) 1.05005(17) 0.0442(5) Uani 1 1 d . . . . .
H3 H 0.297346 0.363610 1.128158 0.053 Uiso 1 1 calc R U . . .
C4 C 0.1905(2) 0.44229(19) 0.99529(17) 0.0450(5) Uani 1 1 d . . . . .
H4 H 0.190517 0.535116 1.036242 0.054 Uiso 1 1 calc R U . . .
C5 C 0.12768(18) 0.41061(17) 0.88162(16) 0.0366(4) Uani 1 1 d . . . . .
H5 H 0.084865 0.481651 0.844397 0.044 Uiso 1 1 calc R U . . .
C6 C 0.12660(15) 0.27563(16) 0.82131(14) 0.0282(3) Uani 1 1 d . . . . .
C7 C 0.05799(17) 0.2384(2) 0.69771(16) 0.0416(4) Uani 1 1 d . . . . .
H7A H 0.003761 0.147675 0.695626 0.050 Uiso 1 1 calc R U . . .
H7B H -0.007792 0.310722 0.683532 0.050 Uiso 1 1 calc R U . . .
C8 C 0.19201(16) 0.34783(18) 0.54993(15) 0.0328(4) Uani 1 1 d . . . . .
C9 C 0.34776(16) 0.42671(15) 0.38944(14) 0.0285(3) Uani 1 1 d . . . . .
C10 C 0.28969(19) 0.54870(17) 0.36568(15) 0.0379(4) Uani 1 1 d . . . . .
H10 H 0.201024 0.573519 0.397775 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3658(2) 0.63408(18) 0.29296(16) 0.0422(4) Uani 1 1 d . . . . .
H11 H 0.329151 0.719359 0.275942 0.051 Uiso 1 1 calc R U . . .
C12 C 0.4939(2) 0.59654(18) 0.24522(17) 0.0421(4) Uani 1 1 d . . . . .
H12 H 0.545056 0.656741 0.196858 0.050 Uiso 1 1 calc R U . . .
C13 C 0.54834(17) 0.47075(17) 0.26765(16) 0.0350(4) Uani 1 1 d . . . . .
H13 H 0.635788 0.444567 0.233706 0.042 Uiso 1 1 calc R U . . .
C14 C 0.47436(16) 0.38414(15) 0.33966(14) 0.0277(3) Uani 1 1 d . . . . .
C15 C 0.51209(15) 0.24631(15) 0.37959(14) 0.0271(3) Uani 1 1 d . . . . .
H15 H 0.586283 0.266988 0.444553 0.033 Uiso 1 1 calc R U . . .
C16 C 0.37539(16) 0.19963(15) 0.44297(14) 0.0284(3) Uani 1 1 d . . . . .
H16 H 0.398193 0.168015 0.523837 0.034 Uiso 1 1 calc R U . . .
C17 C 0.28976(17) 0.08818(17) 0.36710(16) 0.0347(4) Uani 1 1 d . . . . .
C18 C 0.71783(16) 0.16772(15) 0.22037(15) 0.0284(3) Uani 1 1 d . . . . .
C19 C 0.89087(18) 0.21023(19) 0.09044(19) 0.0432(4) Uani 1 1 d . . . . .
H19 H 0.938331 0.226210 0.016928 0.052 Uiso 1 1 calc R U . . .
C20 C 0.94969(18) 0.20627(18) 0.20015(19) 0.0423(4) Uani 1 1 d . . . . .
H20 H 1.046629 0.219003 0.219750 0.051 Uiso 1 1 calc R U . . .
C21 C 0.6477(2) 0.1848(2) 0.00284(17) 0.0448(4) Uani 1 1 d . . . . .
H21A H 0.575727 0.109391 0.008177 0.067 Uiso 1 1 calc R U . . .
H21B H 0.695973 0.168645 -0.076037 0.067 Uiso 1 1 calc R U . . .
H21C H 0.603600 0.274782 0.009033 0.067 Uiso 1 1 calc R U . . .
C22 C 0.86385(19) 0.1642(2) 0.40851(17) 0.0437(4) Uani 1 1 d . . . . .
H22A H 0.869173 0.256623 0.457354 0.066 Uiso 1 1 calc R U . . .
H22B H 0.951253 0.117972 0.417966 0.066 Uiso 1 1 calc R U . . .
H22C H 0.785384 0.107169 0.437000 0.066 Uiso 1 1 calc R U . . .
B1 B 0.56795(19) 0.12554(19) 0.27551(17) 0.0299(4) Uani 1 1 d . . . . .
H1A H 0.4899(18) 0.1012(17) 0.1974(16) 0.035(5) Uiso 1 1 d . . . . .
H1B H 0.5841(19) 0.0223(19) 0.3217(17) 0.046(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.4619(18) . ?
O1 C8 1.352(2) . ?
O2 C8 1.204(2) . ?
N1 C8 1.366(2) . ?
N1 C9 1.416(2) . ?
N1 C16 1.4778(19) . ?
N2 C17 1.139(2) . ?
N3 C18 1.350(2) . ?
N3 C19 1.378(2) . ?
N3 C21 1.462(2) . ?
N4 C18 1.352(2) . ?
N4 C20 1.377(2) . ?
N4 C22 1.456(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.379(3) . ?
C1 C6 1.382(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.372(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(2) . ?
C6 C7 1.500(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C10 1.380(2) . ?
C9 C14 1.390(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.394(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(2) . ?
C14 C15 1.511(2) . ?
C15 H15 1.0000 . ?
C15 C16 1.552(2) . ?
C15 B1 1.638(2) . ?
C16 H16 1.0000 . ?
C16 C17 1.483(2) . ?
C18 B1 1.608(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.333(3) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
B1 H1A 1.130(18) . ?
B1 H1B 1.188(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C7 115.33(13) . . ?
C8 N1 C9 125.23(13) . . ?
C8 N1 C16 124.81(13) . . ?
C9 N1 C16 109.47(12) . . ?
C18 N3 C19 110.30(15) . . ?
C18 N3 C21 125.90(14) . . ?
C19 N3 C21 123.80(15) . . ?
C18 N4 C20 110.74(15) . . ?
C18 N4 C22 125.40(14) . . ?
C20 N4 C22 123.84(15) . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C6 121.21(16) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.50(18) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.98(18) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.51(16) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.25(17) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.55(16) . . ?
C1 C6 C7 120.25(15) . . ?
C5 C6 C7 121.19(16) . . ?
O1 C7 C6 110.63(13) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
O1 C8 N1 109.58(14) . . ?
O2 C8 O1 125.19(15) . . ?
O2 C8 N1 125.21(16) . . ?
C10 C9 N1 128.11(15) . . ?
C10 C9 C14 122.73(15) . . ?
C14 C9 N1 109.15(14) . . ?
C9 C10 H10 121.2 . . ?
C9 C10 C11 117.58(16) . . ?
C11 C10 H10 121.2 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.95(17) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.33(17) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.70(16) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 C15 111.57(13) . . ?
C13 C14 C9 118.64(15) . . ?
C13 C14 C15 129.75(14) . . ?
C14 C15 H15 107.6 . . ?
C14 C15 C16 101.85(12) . . ?
C14 C15 B1 118.41(13) . . ?
C16 C15 H15 107.6 . . ?
C16 C15 B1 113.23(12) . . ?
B1 C15 H15 107.6 . . ?
N1 C16 C15 105.42(12) . . ?
N1 C16 H16 109.8 . . ?
N1 C16 C17 108.05(13) . . ?
C15 C16 H16 109.8 . . ?
C17 C16 C15 113.72(12) . . ?
C17 C16 H16 109.8 . . ?
N2 C17 C16 177.39(17) . . ?
N3 C18 N4 104.87(13) . . ?
N3 C18 B1 127.84(15) . . ?
N4 C18 B1 127.09(14) . . ?
N3 C19 H19 126.3 . . ?
C20 C19 N3 107.42(16) . . ?
C20 C19 H19 126.3 . . ?
N4 C20 H20 126.7 . . ?
C19 C20 N4 106.68(15) . . ?
C19 C20 H20 126.7 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C15 B1 H1A 110.7(8) . . ?
C15 B1 H1B 109.1(9) . . ?
C18 B1 C15 113.11(12) . . ?
C18 B1 H1A 108.9(9) . . ?
C18 B1 H1B 105.6(9) . . ?
H1A B1 H1B 109.4(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C9 C10 C11 178.13(15) . . . . ?
N1 C9 C14 C13 -177.88(13) . . . . ?
N1 C9 C14 C15 -0.13(17) . . . . ?
N3 C18 B1 C15 -117.04(17) . . . . ?
N3 C19 C20 N4 0.1(2) . . . . ?
N4 C18 B1 C15 69.0(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C1 C6 C7 O1 -78.63(19) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
C2 C1 C6 C7 -179.82(15) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C4 C5 C6 C7 179.62(15) . . . . ?
C5 C6 C7 O1 102.14(18) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C7 O1 C8 O2 -2.5(2) . . . . ?
C7 O1 C8 N1 178.67(13) . . . . ?
C8 O1 C7 C6 -92.17(18) . . . . ?
C8 N1 C9 C10 -18.8(3) . . . . ?
C8 N1 C9 C14 162.08(14) . . . . ?
C8 N1 C16 C15 -156.42(14) . . . . ?
C8 N1 C16 C17 81.66(18) . . . . ?
C9 N1 C8 O1 178.78(13) . . . . ?
C9 N1 C8 O2 -0.1(3) . . . . ?
C9 N1 C16 C15 15.87(16) . . . . ?
C9 N1 C16 C17 -106.05(14) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C9 C14 C15 C16 9.52(16) . . . . ?
C9 C14 C15 B1 134.38(14) . . . . ?
C10 C9 C14 C13 2.9(2) . . . . ?
C10 C9 C14 C15 -179.30(14) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C12 C13 C14 C9 -1.0(2) . . . . ?
C12 C13 C14 C15 -178.26(15) . . . . ?
C13 C14 C15 C16 -173.05(15) . . . . ?
C13 C14 C15 B1 -48.2(2) . . . . ?
C14 C9 C10 C11 -2.9(2) . . . . ?
C14 C15 C16 N1 -14.79(15) . . . . ?
C14 C15 C16 C17 103.40(15) . . . . ?
C14 C15 B1 C18 67.08(19) . . . . ?
C16 N1 C8 O1 -10.1(2) . . . . ?
C16 N1 C8 O2 171.02(15) . . . . ?
C16 N1 C9 C10 168.94(15) . . . . ?
C16 N1 C9 C14 -10.18(17) . . . . ?
C16 C15 B1 C18 -173.83(13) . . . . ?
C18 N3 C19 C20 -0.3(2) . . . . ?
C18 N4 C20 C19 0.02(19) . . . . ?
C19 N3 C18 N4 0.26(17) . . . . ?
C19 N3 C18 B1 -174.74(15) . . . . ?
C20 N4 C18 N3 -0.18(17) . . . . ?
C20 N4 C18 B1 174.88(14) . . . . ?
C21 N3 C18 N4 -179.35(15) . . . . ?
C21 N3 C18 B1 5.6(2) . . . . ?
C21 N3 C19 C20 179.37(15) . . . . ?
C22 N4 C18 N3 -178.43(14) . . . . ?
C22 N4 C18 B1 -3.4(2) . . . . ?
C22 N4 C20 C19 178.31(16) . . . . ?
B1 C15 C16 N1 -143.03(13) . . . . ?
B1 C15 C16 C17 -24.84(19) . . . . ?

_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_h2023071003_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2290538'
loop_
_audit_author_name
_audit_author_address
'Yuanyuan An'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-08-24 deposited with the CCDC.	2023-11-12 downloaded from the CCDC.
;
_audit_creation_date             2023-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 B N4 O2'
_chemical_formula_sum            'C22 H21 B N4 O2'
_chemical_formula_weight         384.24
_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                   7.2850(10)
_cell_length_b                   10.3394(14)
_cell_length_c                   15.038(2)
_cell_angle_alpha                71.988(4)
_cell_angle_beta                 76.430(4)
_cell_angle_gamma                75.074(4)
_cell_volume                     1026.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    249(2)
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      2.86
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1413 before and 0.0693 after correction.
The Ratio of minimum to maximum transmission is 0.9352.
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    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27513
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.418
_diffrn_reflns_theta_min         2.114
_diffrn_ambient_temperature      249.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3351
_reflns_number_total             3746
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3746
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.060
_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)+(0.0963P)²+0.3622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1617
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00Q(H00O,H00Q)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00G(H00G), C00H(H00H), C00L(H00L), C00M(H00M),
 C00N(H00N), C00P(H00P), C00R(H00R), C00S(H00S), C00T(H00T)
2.d Idealised Me refined as rotating group:
 C00J(H00A,H00E,H00F), C00K(H00I,H00J,H00K)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.69516(19) 0.69909(14) 0.17755(9) 0.0479(4) Uani 1 1 d . . . . .
O002 O 0.6459(2) 0.60069(16) 0.07157(10) 0.0567(4) Uani 1 1 d . . . . .
N003 N 0.4771(2) 0.56694(15) 0.22207(10) 0.0369(3) Uani 1 1 d . . . . .
N004 N 0.2424(2) 0.17469(15) 0.55007(10) 0.0368(3) Uani 1 1 d . . . . .
N005 N 0.3536(2) 0.11597(14) 0.42010(10) 0.0376(3) Uani 1 1 d . . . . .
N006 N 0.2607(3) 0.84430(18) 0.31205(13) 0.0542(4) Uani 1 1 d . . . . .
C007 C 0.3426(3) 0.73353(18) 0.31421(12) 0.0392(4) Uani 1 1 d . . . . .
C008 C 0.3311(2) 0.50317(16) 0.21555(12) 0.0350(4) Uani 1 1 d . . . . .
C009 C 0.4429(2) 0.58882(17) 0.31732(11) 0.0357(4) Uani 1 1 d . . . . .
H009 H 0.566638 0.568707 0.340290 0.043 Uiso 1 1 calc R . . . .
C00A C 0.2243(2) 0.46266(16) 0.30578(12) 0.0350(4) Uani 1 1 d . . . . .
C00B C 0.3186(2) 0.48159(17) 0.37899(11) 0.0353(4) Uani 1 1 d . . . . .
H00B H 0.222000 0.517976 0.428402 0.042 Uiso 1 1 calc R . . . .
C00C C 0.2425(3) 0.02235(19) 0.47709(14) 0.0441(4) Uani 1 1 d . . . . .
H00C H 0.220021 -0.053237 0.461897 0.053 Uiso 1 1 calc R . . . .
C00D C 0.2909(3) 0.48106(19) 0.13638(13) 0.0421(4) Uani 1 1 d . . . . .
H00D H 0.366712 0.506234 0.076309 0.051 Uiso 1 1 calc R . . . .
C00E C 0.3555(2) 0.21002(17) 0.46499(11) 0.0348(4) Uani 1 1 d . . . . .
C00F C 0.6102(3) 0.62067(18) 0.14929(12) 0.0393(4) Uani 1 1 d . . . . .
C00G C 0.0666(3) 0.40444(19) 0.31665(14) 0.0423(4) Uani 1 1 d . . . . .
H00G H -0.009434 0.379227 0.376663 0.051 Uiso 1 1 calc R . . . .
C00H C 0.1724(3) 0.05918(19) 0.55815(14) 0.0446(4) Uani 1 1 d . . . . .
H00H H 0.090913 0.014712 0.610661 0.054 Uiso 1 1 calc R . . . .
C00I C 0.8206(3) 0.90906(19) 0.11142(12) 0.0431(4) Uani 1 1 d . . . . .
C00J C 0.2017(3) 0.2479(2) 0.62350(14) 0.0496(5) Uani 1 1 d . . . . .
H00A H 0.299520 0.209185 0.663776 0.074 Uiso 1 1 calc GR . . . .
H00E H 0.076171 0.237572 0.661460 0.074 Uiso 1 1 calc GR . . . .
H00F H 0.202240 0.345576 0.594082 0.074 Uiso 1 1 calc GR . . . .
C00K C 0.4468(3) 0.1160(2) 0.32273(13) 0.0489(5) Uani 1 1 d . . . . .
H00I H 0.468744 0.023192 0.314963 0.073 Uiso 1 1 calc GR . . . .
H00J H 0.569041 0.144972 0.309587 0.073 Uiso 1 1 calc GR . . . .
H00K H 0.364249 0.179755 0.279047 0.073 Uiso 1 1 calc GR . . . .
C00L C 0.0218(3) 0.3836(2) 0.23743(15) 0.0484(5) Uani 1 1 d . . . . .
H00L H -0.085322 0.344482 0.244118 0.058 Uiso 1 1 calc R . . . .
C00M C 0.1338(3) 0.4201(2) 0.14942(15) 0.0486(5) Uani 1 1 d . . . . .
H00M H 0.103217 0.403463 0.097109 0.058 Uiso 1 1 calc R . . . .
C00N C 0.9650(3) 0.9531(2) 0.13186(15) 0.0572(5) Uani 1 1 d . . . . .
H00N H 1.078501 0.889261 0.146719 0.069 Uiso 1 1 calc R . . . .
B00O B 0.4654(3) 0.3380(2) 0.42590(14) 0.0402(5) Uani 1 1 d . . . . .
C00P C 0.6555(3) 1.0054(2) 0.09062(16) 0.0588(5) Uani 1 1 d . . . . .
H00P H 0.553591 0.977709 0.077618 0.071 Uiso 1 1 calc R . . . .
C00Q C 0.8460(3) 0.7622(2) 0.10893(19) 0.0639(6) Uani 1 1 d . . . . .
H00O H 0.839337 0.759586 0.045186 0.077 Uiso 1 1 calc R . . . .
H00Q H 0.972625 0.710058 0.124088 0.077 Uiso 1 1 calc R . . . .
C00R C 0.9448(5) 1.0908(3) 0.13076(18) 0.0785(8) Uani 1 1 d . . . . .
H00R H 1.044026 1.119005 0.145681 0.094 Uiso 1 1 calc R . . . .
C00S C 0.7844(6) 1.1842(3) 0.10854(19) 0.0842(9) Uani 1 1 d . . . . .
H00S H 0.772924 1.277638 0.106677 0.101 Uiso 1 1 calc R . . . .
C00T C 0.6388(5) 1.1429(3) 0.08876(18) 0.0785(8) Uani 1 1 d . . . . .
H00T H 0.526395 1.208000 0.073757 0.094 Uiso 1 1 calc R . . . .


_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
O001 C00F 1.347(2) . ?
O001 C00Q 1.456(2) . ?
O002 C00F 1.206(2) . ?
N003 C008 1.423(2) . ?
N003 C009 1.473(2) . ?
N003 C00F 1.360(2) . ?
N004 C00E 1.349(2) . ?
N004 C00H 1.377(2) . ?
N004 C00J 1.459(2) . ?
N005 C00C 1.376(2) . ?
N005 C00E 1.349(2) . ?
N005 C00K 1.462(2) . ?
N006 C007 1.142(2) . ?
C007 C009 1.478(2) . ?
C008 C00A 1.394(2) . ?
C008 C00D 1.386(2) . ?
C009 H009 0.9900 . ?
C009 C00B 1.548(2) . ?
C00A C00B 1.510(2) . ?
C00A C00G 1.384(2) . ?
C00B H00B 0.9900 . ?
C00B B00O 1.653(3) . ?
C00C H00C 0.9400 . ?
C00C C00H 1.337(3) . ?
C00D H00D 0.9400 . ?
C00D C00M 1.391(3) . ?
C00E B00O 1.607(2) . ?
C00G H00G 0.9400 . ?
C00G C00L 1.396(3) . ?
C00H H00H 0.9400 . ?
C00I C00N 1.376(3) . ?
C00I C00P 1.380(3) . ?
C00I C00Q 1.493(3) . ?
C00J H00A 0.9700 . ?
C00J H00E 0.9700 . ?
C00J H00F 0.9700 . ?
C00K H00I 0.9700 . ?
C00K H00J 0.9700 . ?
C00K H00K 0.9700 . ?
C00L H00L 0.9400 . ?
C00L C00M 1.379(3) . ?
C00M H00M 0.9400 . ?
C00N H00N 0.9400 . ?
C00N C00R 1.388(4) . ?
C00P H00P 0.9400 . ?
C00P C00T 1.388(4) . ?
C00Q H00O 0.9800 . ?
C00Q H00Q 0.9800 . ?
C00R H00R 0.9400 . ?
C00R C00S 1.346(5) . ?
C00S H00S 0.9400 . ?
C00S C00T 1.362(5) . ?
C00T H00T 0.9400 . ?

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
C00F O001 C00Q 117.00(16) . . ?
C008 N003 C009 109.37(13) . . ?
C00F N003 C008 126.45(15) . . ?
C00F N003 C009 123.41(14) . . ?
C00E N004 C00H 110.50(15) . . ?
C00E N004 C00J 124.70(15) . . ?
C00H N004 C00J 124.80(15) . . ?
C00C N005 C00K 123.85(15) . . ?
C00E N005 C00C 110.51(15) . . ?
C00E N005 C00K 125.56(15) . . ?
N006 C007 C009 178.20(19) . . ?
C00A C008 N003 108.59(14) . . ?
C00D C008 N003 129.13(16) . . ?
C00D C008 C00A 122.28(16) . . ?
N003 C009 C007 109.64(14) . . ?
N003 C009 H009 110.2 . . ?
N003 C009 C00B 103.61(12) . . ?
C007 C009 H009 110.2 . . ?
C007 C009 C00B 112.76(14) . . ?
C00B C009 H009 110.2 . . ?
C008 C00A C00B 110.06(14) . . ?
C00G C00A C008 119.25(16) . . ?
C00G C00A C00B 130.48(16) . . ?
C009 C00B H00B 111.6 . . ?
C009 C00B B00O 107.92(13) . . ?
C00A C00B C009 101.49(13) . . ?
C00A C00B H00B 111.6 . . ?
C00A C00B B00O 112.11(13) . . ?
B00O C00B H00B 111.6 . . ?
N005 C00C H00C 126.5 . . ?
C00H C00C N005 107.05(15) . . ?
C00H C00C H00C 126.5 . . ?
C008 C00D H00D 121.3 . . ?
C008 C00D C00M 117.33(17) . . ?
C00M C00D H00D 121.3 . . ?
N004 C00E B00O 127.09(15) . . ?
N005 C00E N004 105.02(14) . . ?
N005 C00E B00O 127.89(15) . . ?
O001 C00F N003 109.53(15) . . ?
O002 C00F O001 125.61(16) . . ?
O002 C00F N003 124.86(17) . . ?
C00A C00G H00G 120.4 . . ?
C00A C00G C00L 119.22(17) . . ?
C00L C00G H00G 120.4 . . ?
N004 C00H H00H 126.5 . . ?
C00C C00H N004 106.92(16) . . ?
C00C C00H H00H 126.5 . . ?
C00N C00I C00P 118.0(2) . . ?
C00N C00I C00Q 120.5(2) . . ?
C00P C00I C00Q 121.4(2) . . ?
N004 C00J H00A 109.5 . . ?
N004 C00J H00E 109.5 . . ?
N004 C00J H00F 109.5 . . ?
H00A C00J H00E 109.5 . . ?
H00A C00J H00F 109.5 . . ?
H00E C00J H00F 109.5 . . ?
N005 C00K H00I 109.5 . . ?
N005 C00K H00J 109.5 . . ?
N005 C00K H00K 109.5 . . ?
H00I C00K H00J 109.5 . . ?
H00I C00K H00K 109.5 . . ?
H00J C00K H00K 109.5 . . ?
C00G C00L H00L 119.8 . . ?
C00M C00L C00G 120.41(17) . . ?
C00M C00L H00L 119.8 . . ?
C00D C00M H00M 119.3 . . ?
C00L C00M C00D 121.43(17) . . ?
C00L C00M H00M 119.3 . . ?
C00I C00N H00N 119.7 . . ?
C00I C00N C00R 120.7(2) . . ?
C00R C00N H00N 119.7 . . ?
C00E B00O C00B 110.29(14) . . ?
C00I C00P H00P 119.8 . . ?
C00I C00P C00T 120.4(2) . . ?
C00T C00P H00P 119.8 . . ?
O001 C00Q C00I 109.50(16) . . ?
O001 C00Q H00O 109.8 . . ?
O001 C00Q H00Q 109.8 . . ?
C00I C00Q H00O 109.8 . . ?
C00I C00Q H00Q 109.8 . . ?
H00O C00Q H00Q 108.2 . . ?
C00N C00R H00R 119.7 . . ?
C00S C00R C00N 120.6(3) . . ?
C00S C00R H00R 119.7 . . ?
C00R C00S H00S 120.1 . . ?
C00R C00S C00T 119.8(2) . . ?
C00T C00S H00S 120.1 . . ?
C00P C00T H00T 119.8 . . ?
C00S C00T C00P 120.4(3) . . ?
C00S C00T H00T 119.8 . . ?

_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_cu_231012lu_njlg_ayy_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2304720'
loop_
_audit_author_name
_audit_author_address
'Yuanyuan An'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-10-31 deposited with the CCDC.	2023-11-12 downloaded from the CCDC.
;
_audit_creation_date             2023-10-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 B N4 O2'
_chemical_formula_sum            'C19 H25 B N4 O2'
_chemical_formula_weight         352.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.5060(3)
_cell_length_b                   10.6586(4)
_cell_length_c                   18.9403(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.531(2)
_cell_angle_gamma                90
_cell_volume                     1913.05(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.277
_cell_measurement_theta_min      4.667
_shelx_estimated_absorpt_T_max   0.927
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  0.1665
_exptl_absorpt_correction_T_min  0.0696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0837 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.4180.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34581
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.342
_diffrn_reflns_theta_min         4.666
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_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                3305
_reflns_number_total             3508
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3508
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.046
_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)+(0.0500P)²+0.3468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0952
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,
 H16C), C19(H19A,H19B,H19C)
;
_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
O1 O 0.75526(8) 0.65502(7) 0.47457(4) 0.0428(2) Uani 1 1 d . . . . .
N1 N 0.77927(9) 0.56650(9) 0.36970(5) 0.0390(2) Uani 1 1 d . . . . .
C1 C 0.63513(11) 0.50888(10) 0.36684(6) 0.0385(2) Uani 1 1 d . . . . .
H1 H 0.609033 0.485723 0.415278 0.046 Uiso 1 1 calc R U . . .
B1 B 0.51428(14) 0.59776(13) 0.32606(7) 0.0425(3) Uani 1 1 d . . . . .
H1A H 0.4078(15) 0.5462(13) 0.3238(7) 0.052(3) Uiso 1 1 d . . . . .
H1B H 0.5437(14) 0.6197(13) 0.2716(7) 0.051(4) Uiso 1 1 d . . . . .
O2 O 0.95999(8) 0.68203(8) 0.42152(4) 0.0493(2) Uani 1 1 d . . . . .
N2 N 0.71768(13) 0.18699(10) 0.39517(6) 0.0577(3) Uani 1 1 d . . . . .
C2 C 0.65544(12) 0.38964(10) 0.32096(6) 0.0411(3) Uani 1 1 d . . . . .
H2 H 0.568660 0.374736 0.288673 0.049 Uiso 1 1 calc R U . . .
N3 N 0.40067(10) 0.74926(9) 0.41558(5) 0.0419(2) Uani 1 1 d . . . . .
C3 C 0.69071(12) 0.27543(11) 0.36258(6) 0.0450(3) Uani 1 1 d . . . . .
N4 N 0.55758(10) 0.83889(9) 0.35823(5) 0.0462(2) Uani 1 1 d . . . . .
C4 C 0.77661(11) 0.42702(10) 0.27789(6) 0.0402(2) Uani 1 1 d . . . . .
C5 C 0.82155(13) 0.37304(12) 0.21747(6) 0.0466(3) Uani 1 1 d . . . . .
H5 H 0.775675 0.300777 0.197340 0.056 Uiso 1 1 calc R U . . .
C6 C 0.93495(14) 0.42611(12) 0.18659(6) 0.0514(3) Uani 1 1 d . . . . .
H6 H 0.966822 0.390626 0.144690 0.062 Uiso 1 1 calc R U . . .
C7 C 1.00166(14) 0.53067(12) 0.21675(7) 0.0523(3) Uani 1 1 d . . . . .
H7 H 1.078482 0.566695 0.194742 0.063 Uiso 1 1 calc R U . . .
C8 C 0.95906(13) 0.58434(11) 0.27845(7) 0.0469(3) Uani 1 1 d . . . . .
H8 H 1.006093 0.655607 0.299117 0.056 Uiso 1 1 calc R U . . .
C9 C 0.84575(11) 0.53045(10) 0.30882(6) 0.0396(2) Uani 1 1 d . . . . .
C10 C 0.84195(11) 0.63863(10) 0.42251(6) 0.0393(2) Uani 1 1 d . . . . .
C11 C 0.80528(13) 0.72739(11) 0.53862(6) 0.0448(3) Uani 1 1 d . . . . .
C12 C 0.67520(15) 0.72920(14) 0.58023(7) 0.0579(3) Uani 1 1 d . . . . .
H12A H 0.596926 0.768814 0.551706 0.087 Uiso 1 1 calc R U . . .
H12B H 0.695436 0.776924 0.624089 0.087 Uiso 1 1 calc R U . . .
H12C H 0.649280 0.643040 0.591773 0.087 Uiso 1 1 calc R U . . .
C13 C 0.92585(15) 0.65759(13) 0.57873(7) 0.0561(3) Uani 1 1 d . . . . .
H13A H 0.897471 0.570625 0.586581 0.084 Uiso 1 1 calc R U . . .
H13B H 0.949230 0.698572 0.624470 0.084 Uiso 1 1 calc R U . . .
H13C H 1.008643 0.658530 0.551012 0.084 Uiso 1 1 calc R U . . .
C14 C 0.84647(16) 0.85995(12) 0.51888(7) 0.0573(3) Uani 1 1 d . . . . .
H14A H 0.935688 0.857720 0.496284 0.086 Uiso 1 1 calc R U . . .
H14B H 0.857748 0.911741 0.561708 0.086 Uiso 1 1 calc R U . . .
H14C H 0.772524 0.895824 0.485936 0.086 Uiso 1 1 calc R U . . .
C15 C 0.49357(11) 0.72760(10) 0.36681(6) 0.0398(2) Uani 1 1 d . . . . .
C16 C 0.30338(14) 0.65675(13) 0.44094(7) 0.0523(3) Uani 1 1 d . . . . .
H16A H 0.240097 0.626822 0.401132 0.078 Uiso 1 1 calc R U . . .
H16B H 0.247662 0.695387 0.476506 0.078 Uiso 1 1 calc R U . . .
H16C H 0.357042 0.585889 0.462206 0.078 Uiso 1 1 calc R U . . .
C17 C 0.40587(14) 0.87267(12) 0.43687(7) 0.0517(3) Uani 1 1 d . . . . .
H17 H 0.350479 0.910707 0.470581 0.062 Uiso 1 1 calc R U . . .
C18 C 0.50378(14) 0.92874(12) 0.40103(7) 0.0545(3) Uani 1 1 d . . . . .
H18 H 0.531182 1.014381 0.404397 0.065 Uiso 1 1 calc R U . . .
C19 C 0.67373(14) 0.86128(14) 0.31384(8) 0.0594(4) Uani 1 1 d . . . . .
H19A H 0.762604 0.866062 0.343684 0.089 Uiso 1 1 calc R U . . .
H19B H 0.657876 0.940460 0.288143 0.089 Uiso 1 1 calc R U . . .
H19C H 0.678698 0.792336 0.279896 0.089 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 C10 1.3455(13) . ?
O1 C11 1.4838(13) . ?
N1 C1 1.4986(13) . ?
N1 C9 1.4114(14) . ?
N1 C10 1.3610(14) . ?
C1 H1 1.0000 . ?
C1 B1 1.6351(16) . ?
C1 C2 1.5603(14) . ?
B1 H1A 1.149(14) . ?
B1 H1B 1.115(14) . ?
B1 C15 1.6042(17) . ?
O2 C10 1.2152(14) . ?
N2 C3 1.1447(16) . ?
C2 H2 1.0000 . ?
C2 C3 1.4744(17) . ?
C2 C4 1.5164(16) . ?
N3 C15 1.3474(14) . ?
N3 C16 1.4589(16) . ?
N3 C17 1.3755(15) . ?
N4 C15 1.3489(15) . ?
N4 C18 1.3789(17) . ?
N4 C19 1.4592(17) . ?
C4 C5 1.3785(16) . ?
C4 C9 1.3891(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3869(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.3832(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.3899(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3852(16) . ?
C11 C12 1.5181(18) . ?
C11 C13 1.5188(17) . ?
C11 C14 1.5207(18) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17 0.9500 . ?
C17 C18 1.336(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C10 O1 C11 119.43(8) . . ?
C9 N1 C1 109.02(8) . . ?
C10 N1 C1 127.16(9) . . ?
C10 N1 C9 123.78(9) . . ?
N1 C1 H1 111.1 . . ?
N1 C1 B1 112.70(9) . . ?
N1 C1 C2 101.59(8) . . ?
B1 C1 H1 111.1 . . ?
C2 C1 H1 111.1 . . ?
C2 C1 B1 108.79(9) . . ?
C1 B1 H1A 108.9(7) . . ?
C1 B1 H1B 109.9(7) . . ?
H1A B1 H1B 110.5(10) . . ?
C15 B1 C1 112.39(9) . . ?
C15 B1 H1A 106.8(7) . . ?
C15 B1 H1B 108.3(7) . . ?
C1 C2 H2 109.7 . . ?
C3 C2 C1 114.06(9) . . ?
C3 C2 H2 109.7 . . ?
C3 C2 C4 110.75(9) . . ?
C4 C2 C1 102.61(8) . . ?
C4 C2 H2 109.7 . . ?
C15 N3 C16 125.22(10) . . ?
C15 N3 C17 110.76(10) . . ?
C17 N3 C16 123.98(10) . . ?
N2 C3 C2 179.63(14) . . ?
C15 N4 C18 110.37(10) . . ?
C15 N4 C19 125.61(11) . . ?
C18 N4 C19 123.91(11) . . ?
C5 C4 C2 129.45(11) . . ?
C5 C4 C9 120.93(11) . . ?
C9 C4 C2 109.62(9) . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.82(12) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.04(11) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.62(12) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 121.1 . . ?
C9 C8 C7 117.79(12) . . ?
C9 C8 H8 121.1 . . ?
C4 C9 N1 109.46(10) . . ?
C8 C9 N1 129.74(11) . . ?
C8 C9 C4 120.76(10) . . ?
O1 C10 N1 110.73(9) . . ?
O2 C10 O1 125.57(10) . . ?
O2 C10 N1 123.70(10) . . ?
O1 C11 C12 102.10(9) . . ?
O1 C11 C13 109.56(9) . . ?
O1 C11 C14 110.74(9) . . ?
C12 C11 C13 111.10(11) . . ?
C12 C11 C14 110.60(11) . . ?
C13 C11 C14 112.29(11) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 B1 126.13(10) . . ?
N3 C15 N4 104.96(10) . . ?
N4 C15 B1 128.83(10) . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17 126.6 . . ?
C18 C17 N3 106.82(11) . . ?
C18 C17 H17 126.6 . . ?
N4 C18 H18 126.5 . . ?
C17 C18 N4 107.08(11) . . ?
C17 C18 H18 126.5 . . ?
N4 C19 H19A 109.5 . . ?
N4 C19 H19B 109.5 . . ?
N4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 B1 C15 -64.20(12) . . . . ?
N1 C1 C2 C3 94.39(10) . . . . ?
N1 C1 C2 C4 -25.44(10) . . . . ?
C1 N1 C9 C4 -17.55(12) . . . . ?
C1 N1 C9 C8 160.51(11) . . . . ?
C1 N1 C10 O1 -0.77(15) . . . . ?
C1 N1 C10 O2 179.63(10) . . . . ?
C1 B1 C15 N3 -91.91(13) . . . . ?
C1 B1 C15 N4 91.66(14) . . . . ?
C1 C2 C4 C5 -163.82(11) . . . . ?
C1 C2 C4 C9 16.92(11) . . . . ?
B1 C1 C2 C3 -146.54(10) . . . . ?
B1 C1 C2 C4 93.63(10) . . . . ?
C2 C1 B1 C15 -176.06(9) . . . . ?
C2 C4 C5 C6 178.89(11) . . . . ?
C2 C4 C9 N1 -0.41(12) . . . . ?
C2 C4 C9 C8 -178.67(10) . . . . ?
N3 C17 C18 N4 -0.07(14) . . . . ?
C3 C2 C4 C5 74.07(15) . . . . ?
C3 C2 C4 C9 -105.19(11) . . . . ?
C4 C5 C6 C7 0.57(18) . . . . ?
C5 C4 C9 N1 -179.74(10) . . . . ?
C5 C4 C9 C8 1.99(17) . . . . ?
C5 C6 C7 C8 0.74(19) . . . . ?
C6 C7 C8 C9 -0.69(18) . . . . ?
C7 C8 C9 N1 -178.53(11) . . . . ?
C7 C8 C9 C4 -0.66(17) . . . . ?
C9 N1 C1 B1 -89.29(10) . . . . ?
C9 N1 C1 C2 26.96(11) . . . . ?
C9 N1 C10 O1 -178.28(9) . . . . ?
C9 N1 C10 O2 2.13(17) . . . . ?
C9 C4 C5 C6 -1.92(17) . . . . ?
C10 O1 C11 C12 176.89(10) . . . . ?
C10 O1 C11 C13 -65.28(13) . . . . ?
C10 O1 C11 C14 59.12(13) . . . . ?
C10 N1 C1 B1 92.90(13) . . . . ?
C10 N1 C1 C2 -150.85(10) . . . . ?
C10 N1 C9 C4 160.35(10) . . . . ?
C10 N1 C9 C8 -21.59(18) . . . . ?
C11 O1 C10 N1 177.85(9) . . . . ?
C11 O1 C10 O2 -2.57(16) . . . . ?
C15 N3 C17 C18 -0.20(14) . . . . ?
C15 N4 C18 C17 0.32(14) . . . . ?
C16 N3 C15 B1 1.11(17) . . . . ?
C16 N3 C15 N4 178.23(10) . . . . ?
C16 N3 C17 C18 -178.08(11) . . . . ?
C17 N3 C15 B1 -176.73(10) . . . . ?
C17 N3 C15 N4 0.39(12) . . . . ?
C18 N4 C15 B1 176.58(11) . . . . ?
C18 N4 C15 N3 -0.44(12) . . . . ?
C19 N4 C15 B1 -7.17(18) . . . . ?
C19 N4 C15 N3 175.81(10) . . . . ?
C19 N4 C18 C17 -176.00(11) . . . . ?

_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_ayy_2
_database_code_depnum_ccdc_archive 'CCDC 2304719'
loop_
_audit_author_name
_audit_author_address
'Yuanyuan An'
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-10-31 deposited with the CCDC.	2023-11-12 downloaded from the CCDC.
;
_audit_creation_date             2023-10-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H30 B N3 O4'
_chemical_formula_sum            'C21 H30 B N3 O4'
_chemical_formula_weight         399.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.5158(5)
_cell_length_b                   14.5905(4)
_cell_length_c                   18.9569(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4291.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9248
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.209
_cell_measurement_theta_min      4.770
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.2337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0997 before and 0.0604 after correction.
The Ratio of minimum to maximum transmission is 0.7301.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            93384
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.559
_diffrn_reflns_theta_min         4.665
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.11
_diffrn_source_power             0.05550000000000001
_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                3629
_reflns_number_total             3945
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3945
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.041
_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)+(0.0591P)²+1.3009P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1054
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C11(H11), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C5(H5A,H5B,H5C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C),
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_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
O1 O 0.40552(6) 0.35914(6) 0.46573(5) 0.0376(2) Uani 1 1 d . . . . .
N1 N 0.19225(7) 0.37933(7) 0.57598(6) 0.0336(3) Uani 1 1 d . . . . .
C1 C 0.19872(8) 0.29508(9) 0.60499(7) 0.0307(3) Uani 1 1 d . . . . .
B1 B 0.26967(9) 0.25844(11) 0.66028(8) 0.0339(3) Uani 1 1 d . . . . .
O2 O 0.32036(6) 0.23402(7) 0.48332(4) 0.0363(2) Uani 1 1 d . . . . .
N2 N 0.13124(7) 0.24820(8) 0.57824(6) 0.0340(3) Uani 1 1 d . . . . .
C2 C 0.10993(10) 0.15294(10) 0.59406(9) 0.0473(4) Uani 1 1 d . . . . .
H2A H 0.158884 0.113603 0.581817 0.071 Uiso 1 1 calc R U . . .
H2B H 0.059371 0.134496 0.566519 0.071 Uiso 1 1 calc R U . . .
H2C H 0.097215 0.146786 0.644480 0.071 Uiso 1 1 calc R U . . .
O3 O 0.49835(7) 0.09027(7) 0.60727(5) 0.0489(3) Uani 1 1 d . . . . .
N3 N 0.39505(6) 0.28985(7) 0.57292(5) 0.0280(2) Uani 1 1 d . . . . .
C3 C 0.08417(9) 0.30263(10) 0.53281(8) 0.0410(3) Uani 1 1 d . . . . .
H3 H 0.034164 0.285049 0.507245 0.049 Uiso 1 1 calc R U . . .
O4 O 0.54107(6) 0.11433(6) 0.71867(5) 0.0406(2) Uani 1 1 d . . . . .
C4 C 0.12216(9) 0.38446(10) 0.53163(8) 0.0409(3) Uani 1 1 d . . . . .
H4 H 0.104310 0.436437 0.505222 0.049 Uiso 1 1 calc R U . . .
C5 C 0.25185(10) 0.45532(10) 0.58714(8) 0.0425(3) Uani 1 1 d . . . . .
H5A H 0.289021 0.441784 0.627617 0.064 Uiso 1 1 calc R U . . .
H5B H 0.219139 0.511509 0.596389 0.064 Uiso 1 1 calc R U . . .
H5C H 0.287417 0.463705 0.544911 0.064 Uiso 1 1 calc R U . . .
C6 C 0.35723(8) 0.22003(8) 0.62224(6) 0.0289(3) Uani 1 1 d . . . . .
H6 H 0.345846 0.160950 0.597178 0.035 Uiso 1 1 calc R U . . .
C7 C 0.42967(8) 0.20874(8) 0.67727(6) 0.0279(3) Uani 1 1 d . . . . .
H7 H 0.404216 0.200800 0.725344 0.033 Uiso 1 1 calc R U . . .
C8 C 0.49211(8) 0.13130(8) 0.66191(7) 0.0316(3) Uani 1 1 d . . . . .
C9 C 0.60439(10) 0.04200(10) 0.71199(10) 0.0509(4) Uani 1 1 d . . . . .
H9A H 0.634301 0.047971 0.666691 0.076 Uiso 1 1 calc R U . . .
H9B H 0.575497 -0.017655 0.714219 0.076 Uiso 1 1 calc R U . . .
H9C H 0.646245 0.046716 0.750537 0.076 Uiso 1 1 calc R U . . .
C10 C 0.47705(8) 0.29961(8) 0.67299(6) 0.0266(3) Uani 1 1 d . . . . .
C11 C 0.53491(8) 0.33900(8) 0.71945(6) 0.0291(3) Uani 1 1 d . . . . .
H11 H 0.550112 0.308132 0.761783 0.035 Uiso 1 1 calc R U . . .
C12 C 0.57093(8) 0.42446(8) 0.70386(7) 0.0298(3) Uani 1 1 d . . . . .
C13 C 0.63375(9) 0.46806(9) 0.75449(7) 0.0388(3) Uani 1 1 d . . . . .
H13A H 0.607365 0.472271 0.801353 0.058 Uiso 1 1 calc R U . . .
H13B H 0.648609 0.529641 0.737813 0.058 Uiso 1 1 calc R U . . .
H13C H 0.686067 0.430603 0.757209 0.058 Uiso 1 1 calc R U . . .
C14 C 0.54843(8) 0.46731(8) 0.64106(7) 0.0315(3) Uani 1 1 d . . . . .
H14 H 0.572823 0.525423 0.630454 0.038 Uiso 1 1 calc R U . . .
C15 C 0.49134(8) 0.42799(8) 0.59314(6) 0.0299(3) Uani 1 1 d . . . . .
H15 H 0.477128 0.458101 0.550256 0.036 Uiso 1 1 calc R U . . .
C16 C 0.45584(7) 0.34347(8) 0.60996(6) 0.0266(3) Uani 1 1 d . . . . .
C17 C 0.37584(8) 0.29961(9) 0.50366(6) 0.0293(3) Uani 1 1 d . . . . .
C18 C 0.30131(9) 0.21966(11) 0.40766(7) 0.0402(3) Uani 1 1 d . . . . .
C19 C 0.38361(10) 0.20168(12) 0.36710(8) 0.0464(4) Uani 1 1 d . . . . .
H19A H 0.417945 0.257994 0.365059 0.070 Uiso 1 1 calc R U . . .
H19B H 0.369418 0.181827 0.319098 0.070 Uiso 1 1 calc R U . . .
H19C H 0.416766 0.153573 0.390875 0.070 Uiso 1 1 calc R U . . .
C20 C 0.24617(13) 0.13417(14) 0.40973(9) 0.0680(6) Uani 1 1 d . . . . .
H20A H 0.278746 0.084143 0.431606 0.102 Uiso 1 1 calc R U . . .
H20B H 0.230054 0.116806 0.361561 0.102 Uiso 1 1 calc R U . . .
H20C H 0.193991 0.146201 0.437348 0.102 Uiso 1 1 calc R U . . .
C21 C 0.25206(12) 0.30067(14) 0.37816(8) 0.0599(5) Uani 1 1 d . . . . .
H21A H 0.199811 0.310654 0.406170 0.090 Uiso 1 1 calc R U . . .
H21B H 0.236118 0.288212 0.329064 0.090 Uiso 1 1 calc R U . . .
H21C H 0.288385 0.355555 0.380154 0.090 Uiso 1 1 calc R U . . .
H1A H 0.2882(10) 0.3194(11) 0.6964(8) 0.046(4) Uiso 1 1 d . . . . .
H1B H 0.2388(11) 0.1997(11) 0.6922(9) 0.050(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.2179(15) . ?
N1 C1 1.3505(17) . ?
N1 C4 1.3766(18) . ?
N1 C5 1.4592(17) . ?
C1 B1 1.6113(19) . ?
C1 N2 1.3495(16) . ?
B1 C6 1.6370(19) . ?
B1 H1A 1.159(16) . ?
B1 H1B 1.153(17) . ?
O2 C17 1.3437(15) . ?
O2 C18 1.4792(14) . ?
N2 C2 1.4599(18) . ?
N2 C3 1.3805(18) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
O3 C8 1.2003(16) . ?
N3 C6 1.5021(15) . ?
N3 C16 1.4124(15) . ?
N3 C17 1.3538(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.332(2) . ?
O4 C8 1.3403(16) . ?
O4 C9 1.4474(17) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6 1.0000 . ?
C6 C7 1.5423(17) . ?
C7 H7 1.0000 . ?
C7 C8 1.5165(17) . ?
C7 C10 1.5183(16) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.3827(17) . ?
C10 C16 1.3949(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3980(17) . ?
C12 C13 1.5086(17) . ?
C12 C14 1.3892(18) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C15 1.3925(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3878(17) . ?
C18 C19 1.514(2) . ?
C18 C20 1.513(2) . ?
C18 C21 1.515(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 110.91(11) . . ?
C1 N1 C5 125.84(11) . . ?
C4 N1 C5 123.22(11) . . ?
N1 C1 B1 128.15(11) . . ?
N2 C1 N1 104.51(11) . . ?
N2 C1 B1 127.33(12) . . ?
C1 B1 C6 113.20(10) . . ?
C1 B1 H1A 107.4(8) . . ?
C1 B1 H1B 107.7(8) . . ?
C6 B1 H1A 108.5(8) . . ?
C6 B1 H1B 108.8(8) . . ?
H1A B1 H1B 111.3(11) . . ?
C17 O2 C18 120.47(10) . . ?
C1 N2 C2 125.52(12) . . ?
C1 N2 C3 110.70(11) . . ?
C3 N2 C2 123.78(12) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C16 N3 C6 109.09(9) . . ?
C17 N3 C6 126.08(10) . . ?
C17 N3 C16 124.82(10) . . ?
N2 C3 H3 126.5 . . ?
C4 C3 N2 106.97(12) . . ?
C4 C3 H3 126.5 . . ?
C8 O4 C9 116.69(11) . . ?
N1 C4 H4 126.5 . . ?
C3 C4 N1 106.90(12) . . ?
C3 C4 H4 126.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
B1 C6 H6 111.0 . . ?
N3 C6 B1 111.49(10) . . ?
N3 C6 H6 111.0 . . ?
N3 C6 C7 102.05(9) . . ?
C7 C6 B1 110.08(10) . . ?
C7 C6 H6 111.0 . . ?
C6 C7 H7 109.9 . . ?
C8 C7 C6 114.54(10) . . ?
C8 C7 H7 109.9 . . ?
C8 C7 C10 109.33(10) . . ?
C10 C7 C6 102.91(9) . . ?
C10 C7 H7 109.9 . . ?
O3 C8 O4 123.71(12) . . ?
O3 C8 C7 126.07(12) . . ?
O4 C8 C7 110.22(10) . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 130.05(11) . . ?
C11 C10 C16 120.54(11) . . ?
C16 C10 C7 109.40(10) . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.71(11) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 119.99(11) . . ?
C14 C12 C11 118.82(11) . . ?
C14 C12 C13 121.18(11) . . ?
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 . . ?
C12 C14 H14 118.9 . . ?
C12 C14 C15 122.24(11) . . ?
C15 C14 H14 118.9 . . ?
C14 C15 H15 121.0 . . ?
C16 C15 C14 117.95(11) . . ?
C16 C15 H15 121.0 . . ?
C10 C16 N3 109.23(10) . . ?
C15 C16 N3 130.02(11) . . ?
C15 C16 C10 120.72(11) . . ?
O1 C17 O2 125.50(11) . . ?
O1 C17 N3 124.35(12) . . ?
O2 C17 N3 110.15(10) . . ?
O2 C18 C19 110.40(11) . . ?
O2 C18 C20 101.81(11) . . ?
O2 C18 C21 110.38(12) . . ?
C19 C18 C21 111.92(13) . . ?
C20 C18 C19 110.32(14) . . ?
C20 C18 C21 111.57(15) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 B1 C6 -86.08(16) . . . . ?
N1 C1 N2 C2 -179.78(13) . . . . ?
N1 C1 N2 C3 0.51(14) . . . . ?
C1 N1 C4 C3 0.04(16) . . . . ?
C1 B1 C6 N3 53.62(14) . . . . ?
C1 B1 C6 C7 166.13(10) . . . . ?
C1 N2 C3 C4 -0.50(16) . . . . ?
B1 C1 N2 C2 -0.8(2) . . . . ?
B1 C1 N2 C3 179.51(12) . . . . ?
B1 C6 C7 C8 148.33(10) . . . . ?
B1 C6 C7 C10 -93.11(11) . . . . ?
N2 C1 B1 C6 95.16(15) . . . . ?
N2 C3 C4 N1 0.27(16) . . . . ?
C2 N2 C3 C4 179.78(13) . . . . ?
N3 C6 C7 C8 -93.19(11) . . . . ?
N3 C6 C7 C10 25.37(11) . . . . ?
C4 N1 C1 B1 -179.32(12) . . . . ?
C4 N1 C1 N2 -0.34(14) . . . . ?
C5 N1 C1 B1 2.6(2) . . . . ?
C5 N1 C1 N2 -178.46(12) . . . . ?
C5 N1 C4 C3 178.22(12) . . . . ?
C6 N3 C16 C10 15.49(13) . . . . ?
C6 N3 C16 C15 -162.56(12) . . . . ?
C6 N3 C17 O1 177.29(12) . . . . ?
C6 N3 C17 O2 -3.23(16) . . . . ?
C6 C7 C8 O3 13.10(18) . . . . ?
C6 C7 C8 O4 -167.17(10) . . . . ?
C6 C7 C10 C11 163.58(12) . . . . ?
C6 C7 C10 C16 -17.95(12) . . . . ?
C7 C10 C11 C12 179.77(11) . . . . ?
C7 C10 C16 N3 2.16(13) . . . . ?
C7 C10 C16 C15 -179.59(11) . . . . ?
C8 C7 C10 C11 -74.27(15) . . . . ?
C8 C7 C10 C16 104.19(11) . . . . ?
C9 O4 C8 O3 -0.04(19) . . . . ?
C9 O4 C8 C7 -179.77(11) . . . . ?
C10 C7 C8 O3 -101.77(15) . . . . ?
C10 C7 C8 O4 77.96(12) . . . . ?
C10 C11 C12 C13 179.68(11) . . . . ?
C10 C11 C12 C14 -0.94(17) . . . . ?
C11 C10 C16 N3 -179.21(10) . . . . ?
C11 C10 C16 C15 -0.95(18) . . . . ?
C11 C12 C14 C15 -0.08(18) . . . . ?
C12 C14 C15 C16 0.58(18) . . . . ?
C13 C12 C14 C15 179.29(12) . . . . ?
C14 C15 C16 N3 177.79(12) . . . . ?
C14 C15 C16 C10 -0.07(18) . . . . ?
C16 N3 C6 B1 91.67(11) . . . . ?
C16 N3 C6 C7 -25.80(12) . . . . ?
C16 N3 C17 O1 -4.0(2) . . . . ?
C16 N3 C17 O2 175.48(10) . . . . ?
C16 C10 C11 C12 1.46(18) . . . . ?
C17 O2 C18 C19 56.32(17) . . . . ?
C17 O2 C18 C20 173.47(13) . . . . ?
C17 O2 C18 C21 -67.95(16) . . . . ?
C17 N3 C6 B1 -89.45(14) . . . . ?
C17 N3 C6 C7 153.07(11) . . . . ?
C17 N3 C16 C10 -163.41(11) . . . . ?
C17 N3 C16 C15 18.5(2) . . . . ?
C18 O2 C17 O1 10.33(19) . . . . ?
C18 O2 C17 N3 -169.15(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
