# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2046309'
loop_
_audit_author_name
_audit_author_address
'hui liu'
;Nanjing university
China
;
_audit_update_record             
;
2020-11-25 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;
_audit_creation_date             2020-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C37 H22 B F2 N5 O'
_chemical_formula_sum            'C37 H22 B F2 N5 O'
_chemical_formula_weight         601.40
_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 0.0148 0.0070 '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 0.0073 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0599 0.0411 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   27.1150(7)
_cell_length_b                   11.5861(3)
_cell_length_c                   18.6719(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.1010(10)
_cell_angle_gamma                90
_cell_volume                     5663.3(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9651
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      53.79
_cell_measurement_theta_min      2.94
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.503
_exptl_absorpt_correction_T_max  0.3012
_exptl_absorpt_correction_T_min  0.2278
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0954 before and 0.0524 after correction.
The Ratio of minimum to maximum transmission is 0.7563.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             2480
_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  0.0371
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20966
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.883
_diffrn_reflns_theta_min         2.937
_diffrn_ambient_temperature      193.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3969
_reflns_number_total             5159
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.035
_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)+(0.0402P)²+3.8714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.1016
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C27(H27),
  C30(H30), C33(H33), C34(H34), C35(H35), C36(H36)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.68866(7) 0.50132(18) 0.72535(11) 0.0356(5) Uani 1 1 d . . . . .
C1 C 0.47354(7) 0.01251(15) 0.58779(10) 0.0352(4) Uani 1 1 d . . . . .
C2 C 0.51116(7) -0.03442(16) 0.64415(10) 0.0421(4) Uani 1 1 d . . . . .
H2 H 0.534688 0.013678 0.677740 0.051 Uiso 1 1 calc R . . . .
C3 C 0.51406(8) -0.15338(18) 0.65099(11) 0.0473(5) Uani 1 1 d . . . . .
H3 H 0.540345 -0.187067 0.689095 0.057 Uiso 1 1 calc R . . . .
C4 C 0.47915(8) -0.22437(18) 0.60303(11) 0.0496(5) Uani 1 1 d . . . . .
H4 H 0.482176 -0.305869 0.607829 0.060 Uiso 1 1 calc R . . . .
C5 C 0.44014(8) -0.17656(17) 0.54852(11) 0.0474(5) Uani 1 1 d . . . . .
H5 H 0.415418 -0.225028 0.517198 0.057 Uiso 1 1 calc R . . . .
C6 C 0.43692(7) -0.05661(16) 0.53928(10) 0.0382(4) Uani 1 1 d . . . . .
C7 C 0.40320(6) 0.01924(16) 0.48741(10) 0.0377(4) Uani 1 1 d . . . . .
C8 C 0.36219(7) 0.00132(19) 0.42571(11) 0.0495(5) Uani 1 1 d . . . . .
H8 H 0.349692 -0.074310 0.412084 0.059 Uiso 1 1 calc R . . . .
C9 C 0.34005(8) 0.0963(2) 0.38463(11) 0.0561(6) Uani 1 1 d . . . . .
H9 H 0.311905 0.085078 0.342626 0.067 Uiso 1 1 calc R . . . .
C10 C 0.35778(7) 0.2063(2) 0.40314(10) 0.0494(5) Uani 1 1 d . . . . .
H10 H 0.341563 0.269346 0.373769 0.059 Uiso 1 1 calc R . . . .
C11 C 0.39902(7) 0.22725(18) 0.46405(10) 0.0420(4) Uani 1 1 d . . . . .
H11 H 0.411757 0.303110 0.476237 0.050 Uiso 1 1 calc R . . . .
C12 C 0.42067(6) 0.13283(16) 0.50609(9) 0.0348(4) Uani 1 1 d . . . . .
C13 C 0.38893(6) 0.23387(15) 0.65142(9) 0.0323(4) Uani 1 1 d . . . . .
C14 C 0.40788(7) 0.13838(16) 0.69387(9) 0.0368(4) Uani 1 1 d . . . . .
H14 H 0.443459 0.122283 0.708329 0.044 Uiso 1 1 calc R . . . .
C15 C 0.37324(7) 0.06734(17) 0.71446(10) 0.0428(5) Uani 1 1 d . . . . .
H15 H 0.385258 0.001070 0.743777 0.051 Uiso 1 1 calc R . . . .
C16 C 0.32121(7) 0.09015(17) 0.69345(11) 0.0451(5) Uani 1 1 d . . . . .
H16 H 0.298218 0.038648 0.707724 0.054 Uiso 1 1 calc R . . . .
C17 C 0.30257(7) 0.18638(17) 0.65223(10) 0.0432(5) Uani 1 1 d . . . . .
H17 H 0.266962 0.202190 0.638472 0.052 Uiso 1 1 calc R . . . .
C18 C 0.33659(6) 0.26019(16) 0.63100(9) 0.0353(4) Uani 1 1 d . . . . .
C19 C 0.33084(6) 0.36810(16) 0.59043(9) 0.0362(4) Uani 1 1 d . . . . .
C20 C 0.28855(7) 0.43447(18) 0.55559(11) 0.0480(5) Uani 1 1 d . . . . .
H20 H 0.255192 0.412113 0.557411 0.058 Uiso 1 1 calc R . . . .
C21 C 0.29592(8) 0.53310(19) 0.51844(11) 0.0511(5) Uani 1 1 d . . . . .
H21 H 0.267391 0.579238 0.494630 0.061 Uiso 1 1 calc R . . . .
C22 C 0.34468(7) 0.56572(18) 0.51546(11) 0.0470(5) Uani 1 1 d . . . . .
H22 H 0.348738 0.633616 0.489042 0.056 Uiso 1 1 calc R . . . .
C23 C 0.38737(7) 0.50223(16) 0.54982(10) 0.0405(4) Uani 1 1 d . . . . .
H23 H 0.420581 0.525298 0.547684 0.049 Uiso 1 1 calc R . . . .
C24 C 0.37988(6) 0.40359(15) 0.58754(9) 0.0331(4) Uani 1 1 d . . . . .
C25 C 0.46856(6) 0.31930(15) 0.63005(9) 0.0308(4) Uani 1 1 d . . . . .
C26 C 0.49148(6) 0.22379(15) 0.60439(9) 0.0327(4) Uani 1 1 d . . . . .
C27 C 0.54444(6) 0.22016(15) 0.61549(9) 0.0345(4) Uani 1 1 d . . . . .
H27 H 0.560399 0.155351 0.599831 0.041 Uiso 1 1 calc R . . . .
C28 C 0.57288(6) 0.31230(15) 0.64952(9) 0.0327(4) Uani 1 1 d . . . . .
C29 C 0.55065(6) 0.40754(15) 0.67358(9) 0.0316(4) Uani 1 1 d . . . . .
C30 C 0.49817(6) 0.41294(15) 0.66363(9) 0.0319(4) Uani 1 1 d . . . . .
H30 H 0.482764 0.478642 0.679250 0.038 Uiso 1 1 calc R . . . .
C31 C 0.59264(6) 0.48579(15) 0.71032(9) 0.0316(4) Uani 1 1 d . . . . .
C32 C 0.63146(6) 0.64239(15) 0.77782(9) 0.0341(4) Uani 1 1 d . . . . .
C33 C 0.62676(7) 0.73919(16) 0.81931(10) 0.0402(4) Uani 1 1 d . . . . .
H33 H 0.594100 0.761286 0.824381 0.048 Uiso 1 1 calc R . . . .
C34 C 0.66891(7) 0.80305(17) 0.85300(10) 0.0440(5) Uani 1 1 d . . . . .
H34 H 0.665707 0.867756 0.882713 0.053 Uiso 1 1 calc R . . . .
C35 C 0.71629(7) 0.77286(17) 0.84356(10) 0.0460(5) Uani 1 1 d . . . . .
H35 H 0.745679 0.818022 0.864937 0.055 Uiso 1 1 calc R . . . .
C36 C 0.71975(7) 0.67688(17) 0.80290(10) 0.0429(5) Uani 1 1 d . . . . .
H36 H 0.752193 0.655172 0.796769 0.051 Uiso 1 1 calc R . . . .
C37 C 0.62879(6) 0.33266(15) 0.66642(9) 0.0341(4) Uani 1 1 d . . . . .
F1 F 0.72702(4) 0.43772(10) 0.76943(6) 0.0496(3) Uani 1 1 d . . . . .
F2 F 0.70218(4) 0.54069(10) 0.66345(6) 0.0479(3) Uani 1 1 d . . . . .
N1 N 0.46266(5) 0.12891(12) 0.56850(8) 0.0348(3) Uani 1 1 d . . . . .
N2 N 0.41537(5) 0.32084(12) 0.62425(7) 0.0331(3) Uani 1 1 d . . . . .
N3 N 0.63768(5) 0.43804(12) 0.70401(8) 0.0338(3) Uani 1 1 d . . . . .
N4 N 0.58751(5) 0.58056(12) 0.74370(8) 0.0343(3) Uani 1 1 d . . . . .
N5 N 0.67851(5) 0.61148(13) 0.77097(8) 0.0360(3) Uani 1 1 d . . . . .
O1 O 0.66098(4) 0.27313(11) 0.65003(7) 0.0446(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.362(2) . ?
B1 F2 1.378(2) . ?
B1 N3 1.523(2) . ?
B1 N5 1.598(3) . ?
C1 C2 1.373(2) . ?
C1 C6 1.407(2) . ?
C1 N1 1.407(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.400(3) . ?
C6 C7 1.444(3) . ?
C7 C8 1.393(2) . ?
C7 C12 1.411(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.374(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 N1 1.402(2) . ?
C13 C14 1.380(2) . ?
C13 C18 1.404(2) . ?
C13 N2 1.406(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.374(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(2) . ?
C18 C19 1.449(2) . ?
C19 C20 1.393(2) . ?
C19 C24 1.406(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.381(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(2) . ?
C24 N2 1.404(2) . ?
C25 C26 1.413(2) . ?
C25 C30 1.397(2) . ?
C25 N2 1.418(2) . ?
C26 C27 1.397(2) . ?
C26 N1 1.413(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.372(2) . ?
C28 C29 1.387(2) . ?
C28 C37 1.485(2) . ?
C29 C30 1.388(2) . ?
C29 C31 1.477(2) . ?
C30 H30 0.9500 . ?
C31 N3 1.374(2) . ?
C31 N4 1.288(2) . ?
C32 C33 1.388(2) . ?
C32 N4 1.394(2) . ?
C32 N5 1.363(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.369(2) . ?
C34 H34 0.9500 . ?
C34 C35 1.386(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.363(3) . ?
C36 H36 0.9500 . ?
C36 N5 1.354(2) . ?
C37 N3 1.398(2) . ?
C37 O1 1.213(2) . ?

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
F1 B1 F2 110.96(15) . . ?
F1 B1 N3 113.31(16) . . ?
F1 B1 N5 108.69(15) . . ?
F2 B1 N3 111.19(15) . . ?
F2 B1 N5 107.65(15) . . ?
N3 B1 N5 104.68(14) . . ?
C2 C1 C6 121.80(17) . . ?
C2 C1 N1 129.81(16) . . ?
C6 C1 N1 108.36(15) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.56(18) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.12(19) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.03(19) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.06(18) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 107.63(16) . . ?
C5 C6 C1 118.34(18) . . ?
C5 C6 C7 134.02(17) . . ?
C8 C7 C6 133.93(18) . . ?
C8 C7 C12 119.19(18) . . ?
C12 C7 C6 106.77(15) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.49(19) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.64(18) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.4(2) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 121.4 . . ?
C12 C11 C10 117.16(19) . . ?
C12 C11 H11 121.4 . . ?
C11 C12 C7 122.09(16) . . ?
C11 C12 N1 129.00(16) . . ?
N1 C12 C7 108.84(15) . . ?
C14 C13 C18 121.94(16) . . ?
C14 C13 N2 129.30(15) . . ?
C18 C13 N2 108.71(15) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 C13 117.43(16) . . ?
C15 C14 H14 121.3 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.63(18) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.76(18) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 118.98(17) . . ?
C18 C17 H17 120.5 . . ?
C13 C18 C19 107.03(15) . . ?
C17 C18 C13 119.22(17) . . ?
C17 C18 C19 133.73(16) . . ?
C20 C19 C18 133.14(17) . . ?
C20 C19 C24 119.49(17) . . ?
C24 C19 C18 107.36(15) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.89(18) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.64(18) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.1 . . ?
C23 C22 C21 121.85(19) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 H23 121.3 . . ?
C22 C23 C24 117.37(17) . . ?
C24 C23 H23 121.3 . . ?
C23 C24 C19 121.75(16) . . ?
C23 C24 N2 129.72(16) . . ?
N2 C24 C19 108.44(15) . . ?
C26 C25 N2 120.84(14) . . ?
C30 C25 C26 120.54(14) . . ?
C30 C25 N2 118.59(15) . . ?
C27 C26 C25 119.96(15) . . ?
C27 C26 N1 117.85(15) . . ?
N1 C26 C25 122.17(14) . . ?
C26 C27 H27 120.7 . . ?
C28 C27 C26 118.51(16) . . ?
C28 C27 H27 120.7 . . ?
C27 C28 C29 121.98(15) . . ?
C27 C28 C37 129.92(16) . . ?
C29 C28 C37 108.10(15) . . ?
C28 C29 C30 120.64(15) . . ?
C28 C29 C31 106.93(14) . . ?
C30 C29 C31 132.38(16) . . ?
C25 C30 H30 120.8 . . ?
C29 C30 C25 118.32(16) . . ?
C29 C30 H30 120.8 . . ?
N3 C31 C29 107.94(15) . . ?
N4 C31 C29 125.50(15) . . ?
N4 C31 N3 126.54(15) . . ?
C33 C32 N4 118.60(15) . . ?
N5 C32 C33 119.28(16) . . ?
N5 C32 N4 122.12(16) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 C32 120.41(17) . . ?
C34 C33 H33 119.8 . . ?
C33 C34 H34 120.1 . . ?
C33 C34 C35 119.70(18) . . ?
C35 C34 H34 120.1 . . ?
C34 C35 H35 120.7 . . ?
C36 C35 C34 118.50(17) . . ?
C36 C35 H35 120.7 . . ?
C35 C36 H36 118.9 . . ?
N5 C36 C35 122.20(17) . . ?
N5 C36 H36 118.9 . . ?
N3 C37 C28 106.17(14) . . ?
O1 C37 C28 128.18(16) . . ?
O1 C37 N3 125.62(16) . . ?
C1 N1 C26 124.83(14) . . ?
C12 N1 C1 108.33(14) . . ?
C12 N1 C26 126.75(15) . . ?
C13 N2 C25 124.59(14) . . ?
C24 N2 C13 108.45(13) . . ?
C24 N2 C25 126.87(14) . . ?
C31 N3 B1 123.39(15) . . ?
C31 N3 C37 110.74(14) . . ?
C37 N3 B1 125.31(14) . . ?
C31 N4 C32 118.17(14) . . ?
C32 N5 B1 123.75(14) . . ?
C36 N5 B1 116.40(14) . . ?
C36 N5 C32 119.85(16) . . ?

_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_3b
_database_code_depnum_ccdc_archive 'CCDC 2046310'
loop_
_audit_author_name
_audit_author_address
'hui liu'
;Nanjing university
China
;
_audit_update_record             
;
2020-11-25 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H22 B F2 N5 O'
_chemical_formula_weight         625.42

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.939(8)
_cell_length_b                   9.493(8)
_cell_length_c                   17.408(16)
_cell_angle_alpha                88.857(13)
_cell_angle_beta                 84.196(14)
_cell_angle_gamma                88.477(12)
_cell_volume                     1469(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1487
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      22.10

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12548
_diffrn_reflns_av_unetI/netI     0.1032
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.146
_diffrn_reflns_theta_max         26.859
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             6178
_reflns_number_gt                3099
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1853P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6178
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.2032
_refine_ls_wR_factor_gt          0.1534
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.2033(4) 0.6774(4) 0.4962(2) 0.0383(9) Uani 1 1 d . . . . .
C1 C 0.7066(4) 0.2398(3) 0.1746(2) 0.0395(8) Uani 1 1 d . . . . .
F1 F 0.1860(3) 0.6036(2) 0.56361(12) 0.0629(7) Uani 1 1 d . . . . .
N1 N 0.7752(3) 0.3394(3) 0.21669(16) 0.0398(7) Uani 1 1 d . . . . .
O1 O 0.3318(3) 0.3939(2) 0.45199(16) 0.0599(8) Uani 1 1 d . . . . .
C2 C 0.9184(4) 0.2875(3) 0.2315(2) 0.0374(8) Uani 1 1 d . . . . .
F2 F 0.0832(2) 0.6647(2) 0.45410(14) 0.0604(6) Uani 1 1 d . . . . .
N2 N 0.8377(3) 0.6289(3) 0.18604(15) 0.0363(6) Uani 1 1 d . . . . .
C3 C 0.9421(4) 0.1557(3) 0.1947(2) 0.0429(9) Uani 1 1 d . . . . .
N3 N 0.3502(3) 0.6379(2) 0.44691(15) 0.0353(6) Uani 1 1 d . . . . .
C4 C 0.8093(4) 0.1273(3) 0.1584(2) 0.0444(9) Uani 1 1 d . . . . .
N4 N 0.2143(3) 0.8413(3) 0.51417(16) 0.0361(6) Uani 1 1 d . . . . .
C5 C 0.5655(4) 0.2413(4) 0.1496(2) 0.0476(9) Uani 1 1 d . . . . .
H5 H 0.498383 0.316460 0.160576 0.057 Uiso 1 1 calc R U . . .
N5 N 0.5705(4) 1.0515(3) 0.3293(2) 0.0610(9) Uani 1 1 d . . . . .
C6 C 1.0207(4) 0.3429(4) 0.2750(2) 0.0470(9) Uani 1 1 d . . . . .
H6 H 1.001129 0.427745 0.300347 0.056 Uiso 1 1 calc R U . . .
C7 C 1.1567(4) 0.2669(4) 0.2799(2) 0.0583(11) Uani 1 1 d . . . . .
H7 H 1.230231 0.302498 0.307842 0.070 Uiso 1 1 calc R U . . .
C8 C 0.5258(5) 0.1281(4) 0.1077(2) 0.0638(11) Uani 1 1 d . . . . .
H8 H 0.430353 0.127062 0.090880 0.077 Uiso 1 1 calc R U . . .
C9 C 0.7689(5) 0.0165(4) 0.1148(2) 0.0600(11) Uani 1 1 d . . . . .
H9 H 0.837051 -0.057049 0.102004 0.072 Uiso 1 1 calc R U . . .
C10 C 1.0774(4) 0.0848(4) 0.2010(2) 0.0565(10) Uani 1 1 d . . . . .
H10 H 1.097747 -0.000449 0.176144 0.068 Uiso 1 1 calc R U . . .
C11 C 1.1810(4) 0.1395(4) 0.2435(3) 0.0587(11) Uani 1 1 d . . . . .
H11 H 1.270732 0.089629 0.247989 0.070 Uiso 1 1 calc R U . . .
C12 C 0.6252(5) 0.0164(4) 0.0904(3) 0.0700(12) Uani 1 1 d . . . . .
H12 H 0.596064 -0.058790 0.062353 0.084 Uiso 1 1 calc R U . . .
C13 C 0.9468(4) 0.6676(3) 0.0633(2) 0.0399(8) Uani 1 1 d . . . . .
C14 C 0.8144(4) 0.6248(3) 0.10785(19) 0.0357(8) Uani 1 1 d . . . . .
C15 C 1.0539(4) 0.6966(3) 0.1169(2) 0.0415(8) Uani 1 1 d . . . . .
C16 C 0.9834(4) 0.6752(3) 0.1919(2) 0.0381(8) Uani 1 1 d . . . . .
C17 C 0.6878(4) 0.5906(4) 0.0747(2) 0.0484(9) Uani 1 1 d . . . . .
H17 H 0.601427 0.562482 0.104790 0.058 Uiso 1 1 calc R U . . .
C18 C 1.0554(4) 0.6968(4) 0.2575(2) 0.0472(9) Uani 1 1 d . . . . .
H18 H 1.007099 0.685000 0.306989 0.057 Uiso 1 1 calc R U . . .
C19 C 0.9487(5) 0.6746(4) -0.0163(2) 0.0566(10) Uani 1 1 d . . . . .
H19 H 1.034621 0.701879 -0.046988 0.068 Uiso 1 1 calc R U . . .
C20 C 0.8204(5) 0.6402(4) -0.0492(2) 0.0631(11) Uani 1 1 d . . . . .
H20 H 0.820531 0.645045 -0.102660 0.076 Uiso 1 1 calc R U . . .
C21 C 1.2054(4) 0.7379(4) 0.1084(3) 0.0596(11) Uani 1 1 d . . . . .
H21 H 1.254760 0.753062 0.059394 0.071 Uiso 1 1 calc R U . . .
C22 C 0.6928(5) 0.5991(4) -0.0047(2) 0.0582(11) Uani 1 1 d . . . . .
H22 H 0.608230 0.576603 -0.028532 0.070 Uiso 1 1 calc R U . . .
C23 C 1.2793(5) 0.7556(5) 0.1725(3) 0.0679(13) Uani 1 1 d . . . . .
H23 H 1.379943 0.779968 0.167318 0.081 Uiso 1 1 calc R U . . .
C24 C 1.2033(5) 0.7370(4) 0.2447(3) 0.0640(12) Uani 1 1 d . . . . .
H24 H 1.254833 0.752442 0.287433 0.077 Uiso 1 1 calc R U . . .
C25 C 0.7308(3) 0.5898(3) 0.24740(18) 0.0329(7) Uani 1 1 d . . . . .
C26 C 0.5421(3) 0.6548(3) 0.34832(18) 0.0316(7) Uani 1 1 d . . . . .
C27 C 0.6538(3) 0.6945(3) 0.29168(19) 0.0345(8) Uani 1 1 d . . . . .
H27 H 0.676879 0.788879 0.283350 0.041 Uiso 1 1 calc R U . . .
C28 C 0.5101(4) 0.5111(3) 0.36035(19) 0.0356(8) Uani 1 1 d . . . . .
C29 C 0.6966(4) 0.4475(3) 0.25995(19) 0.0356(8) Uani 1 1 d . . . . .
C30 C 0.5828(4) 0.4085(3) 0.3173(2) 0.0395(8) Uani 1 1 d . . . . .
H30 H 0.558034 0.314511 0.325588 0.047 Uiso 1 1 calc R U . . .
C31 C 0.3888(4) 0.4996(3) 0.4240(2) 0.0400(8) Uani 1 1 d . . . . .
C32 C 0.4355(3) 0.7316(3) 0.40324(18) 0.0305(7) Uani 1 1 d . . . . .
C33 C 0.4130(3) 0.8736(3) 0.41185(19) 0.0332(7) Uani 1 1 d . . . . .
C34 C 0.3013(3) 0.9316(3) 0.47036(19) 0.0325(7) Uani 1 1 d . . . . .
C35 C 0.2870(4) 1.0755(3) 0.4830(2) 0.0429(8) Uani 1 1 d . . . . .
H35 H 0.346090 1.138224 0.452435 0.051 Uiso 1 1 calc R U . . .
C36 C 0.1843(4) 1.1243(4) 0.5414(2) 0.0476(9) Uani 1 1 d . . . . .
H36 H 0.172424 1.220636 0.549536 0.057 Uiso 1 1 calc R U . . .
C37 C 0.1154(4) 0.8914(4) 0.5722(2) 0.0479(9) Uani 1 1 d . . . . .
H37 H 0.056494 0.828262 0.602668 0.058 Uiso 1 1 calc R U . . .
C38 C 0.1003(4) 1.0323(4) 0.5871(2) 0.0487(9) Uani 1 1 d . . . . .
H38 H 0.033633 1.064654 0.627761 0.058 Uiso 1 1 calc R U . . .
C39 C 0.5024(4) 0.9708(3) 0.3654(2) 0.0400(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.352(4) . ?
B1 F2 1.370(4) . ?
B1 N3 1.537(5) . ?
B1 N4 1.601(5) . ?
C1 C5 1.375(5) . ?
C1 N1 1.398(4) . ?
C1 C4 1.404(5) . ?
N1 C2 1.406(4) . ?
N1 C29 1.414(4) . ?
O1 C31 1.209(4) . ?
C2 C6 1.367(5) . ?
C2 C3 1.418(5) . ?
N2 C16 1.399(4) . ?
N2 C14 1.399(4) . ?
N2 C25 1.410(4) . ?
C3 C10 1.382(5) . ?
C3 C4 1.434(5) . ?
N3 C32 1.357(4) . ?
N3 C31 1.404(4) . ?
C4 C9 1.385(5) . ?
N4 C34 1.345(4) . ?
N4 C37 1.358(4) . ?
C5 C8 1.385(5) . ?
C5 H5 0.9300 . ?
N5 C39 1.132(4) . ?
C6 C7 1.407(5) . ?
C6 H6 0.9300 . ?
C7 C11 1.378(6) . ?
C7 H7 0.9300 . ?
C8 C12 1.382(6) . ?
C8 H8 0.9300 . ?
C9 C12 1.394(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.362(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C19 1.385(5) . ?
C13 C14 1.412(5) . ?
C13 C15 1.437(5) . ?
C14 C17 1.370(5) . ?
C15 C16 1.404(5) . ?
C15 C21 1.413(5) . ?
C16 C18 1.388(5) . ?
C17 C22 1.380(5) . ?
C17 H17 0.9300 . ?
C18 C24 1.381(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(6) . ?
C19 H19 0.9300 . ?
C20 C22 1.374(6) . ?
C20 H20 0.9300 . ?
C21 C23 1.368(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.377(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C27 1.394(4) . ?
C25 C29 1.400(4) . ?
C26 C27 1.384(4) . ?
C26 C28 1.409(4) . ?
C26 C32 1.470(4) . ?
C27 H27 0.9300 . ?
C28 C30 1.352(4) . ?
C28 C31 1.474(5) . ?
C29 C30 1.404(5) . ?
C30 H30 0.9300 . ?
C32 C33 1.366(4) . ?
C33 C39 1.422(5) . ?
C33 C34 1.458(4) . ?
C34 C35 1.389(4) . ?
C35 C36 1.377(5) . ?
C35 H35 0.9300 . ?
C36 C38 1.358(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.369(5) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 B1 F2 112.1(3) . . ?
F1 B1 N3 112.6(3) . . ?
F2 B1 N3 110.2(3) . . ?
F1 B1 N4 109.1(3) . . ?
F2 B1 N4 106.7(3) . . ?
N3 B1 N4 105.7(3) . . ?
C5 C1 N1 130.1(3) . . ?
C5 C1 C4 121.5(3) . . ?
N1 C1 C4 108.4(3) . . ?
C1 N1 C2 109.0(3) . . ?
C1 N1 C29 124.3(3) . . ?
C2 N1 C29 123.2(3) . . ?
C6 C2 N1 129.8(3) . . ?
C6 C2 C3 122.6(3) . . ?
N1 C2 C3 107.5(3) . . ?
C16 N2 C14 108.6(3) . . ?
C16 N2 C25 126.9(3) . . ?
C14 N2 C25 124.6(3) . . ?
C10 C3 C2 117.8(3) . . ?
C10 C3 C4 134.6(3) . . ?
C2 C3 C4 107.5(3) . . ?
C32 N3 C31 110.4(3) . . ?
C32 N3 B1 124.0(3) . . ?
C31 N3 B1 123.2(3) . . ?
C9 C4 C1 119.3(4) . . ?
C9 C4 C3 133.2(3) . . ?
C1 C4 C3 107.5(3) . . ?
C34 N4 C37 119.6(3) . . ?
C34 N4 B1 124.0(3) . . ?
C37 N4 B1 115.9(3) . . ?
C1 C5 C8 118.3(4) . . ?
C1 C5 H5 120.8 . . ?
C8 C5 H5 120.8 . . ?
C2 C6 C7 117.5(3) . . ?
C2 C6 H6 121.2 . . ?
C7 C6 H6 121.2 . . ?
C11 C7 C6 120.0(4) . . ?
C11 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C12 C8 C5 121.3(4) . . ?
C12 C8 H8 119.3 . . ?
C5 C8 H8 119.3 . . ?
C4 C9 C12 119.4(4) . . ?
C4 C9 H9 120.3 . . ?
C12 C9 H9 120.3 . . ?
C11 C10 C3 120.1(4) . . ?
C11 C10 H10 120.0 . . ?
C3 C10 H10 120.0 . . ?
C10 C11 C7 121.9(4) . . ?
C10 C11 H11 119.1 . . ?
C7 C11 H11 119.1 . . ?
C8 C12 C9 120.1(4) . . ?
C8 C12 H12 120.0 . . ?
C9 C12 H12 120.0 . . ?
C19 C13 C14 118.8(3) . . ?
C19 C13 C15 134.5(3) . . ?
C14 C13 C15 106.6(3) . . ?
C17 C14 N2 129.3(3) . . ?
C17 C14 C13 122.1(3) . . ?
N2 C14 C13 108.6(3) . . ?
C16 C15 C21 118.3(4) . . ?
C16 C15 C13 107.8(3) . . ?
C21 C15 C13 133.8(4) . . ?
C18 C16 N2 129.2(3) . . ?
C18 C16 C15 122.6(3) . . ?
N2 C16 C15 108.2(3) . . ?
C14 C17 C22 117.8(4) . . ?
C14 C17 H17 121.1 . . ?
C22 C17 H17 121.1 . . ?
C24 C18 C16 115.8(4) . . ?
C24 C18 H18 122.1 . . ?
C16 C18 H18 122.1 . . ?
C20 C19 C13 118.7(4) . . ?
C20 C19 H19 120.6 . . ?
C13 C19 H19 120.6 . . ?
C22 C20 C19 121.3(4) . . ?
C22 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C23 C21 C15 119.8(4) . . ?
C23 C21 H21 120.1 . . ?
C15 C21 H21 120.1 . . ?
C20 C22 C17 121.2(4) . . ?
C20 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
C21 C23 C24 119.4(4) . . ?
C21 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C23 C24 C18 124.1(4) . . ?
C23 C24 H24 118.0 . . ?
C18 C24 H24 118.0 . . ?
C27 C25 C29 120.9(3) . . ?
C27 C25 N2 119.2(3) . . ?
C29 C25 N2 119.7(3) . . ?
C27 C26 C28 119.7(3) . . ?
C27 C26 C32 134.5(3) . . ?
C28 C26 C32 105.8(3) . . ?
C26 C27 C25 118.5(3) . . ?
C26 C27 H27 120.8 . . ?
C25 C27 H27 120.8 . . ?
C30 C28 C26 122.4(3) . . ?
C30 C28 C31 129.5(3) . . ?
C26 C28 C31 108.1(3) . . ?
C25 C29 C30 120.1(3) . . ?
C25 C29 N1 121.8(3) . . ?
C30 C29 N1 118.0(3) . . ?
C28 C30 C29 118.3(3) . . ?
C28 C30 H30 120.8 . . ?
C29 C30 H30 120.8 . . ?
O1 C31 N3 125.6(3) . . ?
O1 C31 C28 128.1(3) . . ?
N3 C31 C28 106.3(3) . . ?
N3 C32 C33 121.3(3) . . ?
N3 C32 C26 109.3(3) . . ?
C33 C32 C26 129.3(3) . . ?
C32 C33 C39 120.8(3) . . ?
C32 C33 C34 121.8(3) . . ?
C39 C33 C34 117.4(3) . . ?
N4 C34 C35 120.1(3) . . ?
N4 C34 C33 118.2(3) . . ?
C35 C34 C33 121.6(3) . . ?
C36 C35 C34 119.3(3) . . ?
C36 C35 H35 120.3 . . ?
C34 C35 H35 120.3 . . ?
C38 C36 C35 120.3(3) . . ?
C38 C36 H36 119.9 . . ?
C35 C36 H36 119.9 . . ?
N4 C37 C38 121.7(3) . . ?
N4 C37 H37 119.2 . . ?
C38 C37 H37 119.2 . . ?
C36 C38 C37 118.9(3) . . ?
C36 C38 H38 120.5 . . ?
C37 C38 H38 120.5 . . ?
N5 C39 C33 177.8(4) . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.058

