# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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 
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data_mj21493_0m
_database_code_depnum_ccdc_archive 'CCDC 2124830'
loop_
_audit_author_name
_audit_author_address
'Shuaipeng Lv'
;Shanghai University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2021-11-29 deposited with the CCDC.	2023-04-05 downloaded from the CCDC.
;
_audit_creation_date             2021-10-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 N2'
_chemical_formula_sum            'C25 H24 N2'
_chemical_formula_weight         352.46
_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 0.0137 0.0067 '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'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.40750(10)
_cell_length_b                   22.1588(4)
_cell_length_c                   13.6261(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.7770(10)
_cell_angle_gamma                90
_cell_volume                     1906.57(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    213.00
_cell_measurement_theta_max      54.886
_cell_measurement_theta_min      4.503
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0996 before and 0.0502 after correction.
The Ratio of minimum to maximum transmission is 0.8129.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19212
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.869
_diffrn_reflns_theta_min         4.501
_diffrn_ambient_temperature      213.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.85
_diffrn_source_power             0.19887300000000002
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3079
_reflns_number_total             3592
_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 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         0.169
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.066
_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)+(0.0523P)²+0.4513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1134
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.57469(16) 0.31011(5) 0.74855(8) 0.0361(3) Uani 1 1 d . . . . .
N2 N 0.37403(17) 0.41615(5) 0.46596(8) 0.0393(3) Uani 1 1 d . . . . .
C1 C 0.42765(19) 0.29419(5) 0.65565(9) 0.0324(3) Uani 1 1 d . . . . .
H1 H 0.282268 0.297626 0.670661 0.039 Uiso 1 1 calc R U . . .
C2 C 0.4595(2) 0.22854(6) 0.63035(9) 0.0353(3) Uani 1 1 d . . . . .
C3 C 0.2990(2) 0.19886(6) 0.56708(10) 0.0458(3) Uani 1 1 d . . . . .
H3 H 0.174956 0.219913 0.540420 0.055 Uiso 1 1 calc R U . . .
C4 C 0.3193(3) 0.13879(7) 0.54276(12) 0.0578(4) Uani 1 1 d . . . . .
H4 H 0.208662 0.118931 0.500933 0.069 Uiso 1 1 calc R U . . .
C5 C 0.5025(3) 0.10837(7) 0.58028(12) 0.0617(5) Uani 1 1 d . . . . .
H5 H 0.517898 0.067629 0.563661 0.074 Uiso 1 1 calc R U . . .
C6 C 0.6634(3) 0.13747(7) 0.64213(12) 0.0545(4) Uani 1 1 d . . . . .
H6 H 0.788699 0.116350 0.666653 0.065 Uiso 1 1 calc R U . . .
C7 C 0.6443(2) 0.19775(6) 0.66916(10) 0.0410(3) Uani 1 1 d . . . . .
C8 C 0.8187(2) 0.22774(7) 0.74001(12) 0.0514(4) Uani 1 1 d . . . . .
H8A H 0.954827 0.218019 0.720205 0.062 Uiso 1 1 calc R U . . .
H8B H 0.820453 0.211444 0.807010 0.062 Uiso 1 1 calc R U . . .
C9 C 0.7946(2) 0.29582(6) 0.74311(11) 0.0436(3) Uani 1 1 d . . . . .
H9A H 0.888117 0.312262 0.801368 0.052 Uiso 1 1 calc R U . . .
H9B H 0.833956 0.313882 0.683189 0.052 Uiso 1 1 calc R U . . .
C10 C 0.5354(2) 0.36762(6) 0.78747(9) 0.0399(3) Uani 1 1 d . . . . .
C11 C 0.3565(3) 0.37500(8) 0.83176(12) 0.0564(4) Uani 1 1 d . . . . .
H11 H 0.265172 0.342165 0.835196 0.068 Uiso 1 1 calc R U . . .
C12 C 0.3123(4) 0.43023(10) 0.87072(14) 0.0775(6) Uani 1 1 d . . . . .
H12 H 0.189261 0.435011 0.898925 0.093 Uiso 1 1 calc R U . . .
C13 C 0.4482(4) 0.47845(9) 0.86840(14) 0.0821(7) Uani 1 1 d . . . . .
H13 H 0.418765 0.515904 0.895435 0.099 Uiso 1 1 calc R U . . .
C14 C 0.6247(4) 0.47119(8) 0.82662(13) 0.0733(6) Uani 1 1 d . . . . .
H14 H 0.718010 0.503833 0.825606 0.088 Uiso 1 1 calc R U . . .
C15 C 0.6695(3) 0.41642(7) 0.78548(11) 0.0532(4) Uani 1 1 d . . . . .
H15 H 0.791347 0.412434 0.756121 0.064 Uiso 1 1 calc R U . . .
C16 C 0.43967(19) 0.33614(5) 0.56871(9) 0.0323(3) Uani 1 1 d . . . . .
C17 C 0.3142(2) 0.38620(6) 0.54592(9) 0.0353(3) Uani 1 1 d . . . . .
C18 C 0.1350(2) 0.40981(7) 0.59116(11) 0.0474(4) Uani 1 1 d . . . . .
H18A H 0.171966 0.449126 0.620308 0.071 Uiso 1 1 calc R U . . .
H18B H 0.106010 0.382258 0.642515 0.071 Uiso 1 1 calc R U . . .
H18C H 0.010082 0.413440 0.540165 0.071 Uiso 1 1 calc R U . . .
C19 C 0.2719(3) 0.46910(7) 0.41697(12) 0.0556(4) Uani 1 1 d . . . . .
H19A H 0.155593 0.456689 0.365776 0.083 Uiso 1 1 calc R U . . .
H19B H 0.373712 0.491925 0.386852 0.083 Uiso 1 1 calc R U . . .
H19C H 0.218021 0.494099 0.465500 0.083 Uiso 1 1 calc R U . . .
C20 C 0.5378(2) 0.38527(6) 0.43543(9) 0.0363(3) Uani 1 1 d . . . . .
C21 C 0.6481(2) 0.39846(7) 0.35836(10) 0.0445(3) Uani 1 1 d . . . . .
H21 H 0.618076 0.433426 0.319462 0.053 Uiso 1 1 calc R U . . .
C22 C 0.8023(2) 0.35863(7) 0.34107(11) 0.0500(4) Uani 1 1 d . . . . .
H22 H 0.879529 0.366528 0.289656 0.060 Uiso 1 1 calc R U . . .
C23 C 0.8461(2) 0.30657(7) 0.39882(11) 0.0494(4) Uani 1 1 d . . . . .
H23 H 0.950182 0.279575 0.384706 0.059 Uiso 1 1 calc R U . . .
C24 C 0.7392(2) 0.29413(6) 0.47610(10) 0.0419(3) Uani 1 1 d . . . . .
H24 H 0.770983 0.259024 0.514443 0.050 Uiso 1 1 calc R U . . .
C25 C 0.58240(19) 0.33407(5) 0.49744(9) 0.0337(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
N1 C1 1.4865(16) . ?
N1 C9 1.4584(17) . ?
N1 C10 1.4192(17) . ?
N2 C17 1.3842(17) . ?
N2 C19 1.4499(17) . ?
N2 C20 1.3751(16) . ?
C1 H1 0.9900 . ?
C1 C2 1.5165(17) . ?
C1 C16 1.5181(17) . ?
C2 C3 1.3899(19) . ?
C2 C7 1.3912(18) . ?
C3 H3 0.9400 . ?
C3 C4 1.383(2) . ?
C4 H4 0.9400 . ?
C4 C5 1.375(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.376(2) . ?
C6 H6 0.9400 . ?
C6 C7 1.397(2) . ?
C7 C8 1.502(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 C9 1.518(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.393(2) . ?
C10 C15 1.384(2) . ?
C11 H11 0.9400 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9400 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9400 . ?
C13 C14 1.360(3) . ?
C14 H14 0.9400 . ?
C14 C15 1.387(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.3741(17) . ?
C16 C25 1.4432(17) . ?
C17 C18 1.4877(18) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 C21 1.3927(19) . ?
C20 C25 1.4145(18) . ?
C21 H21 0.9400 . ?
C21 C22 1.375(2) . ?
C22 H22 0.9400 . ?
C22 C23 1.398(2) . ?
C23 H23 0.9400 . ?
C23 C24 1.378(2) . ?
C24 H24 0.9400 . ?
C24 C25 1.4056(18) . ?

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
C9 N1 C1 112.54(10) . . ?
C10 N1 C1 113.86(10) . . ?
C10 N1 C9 116.62(11) . . ?
C17 N2 C19 125.92(12) . . ?
C20 N2 C17 109.09(10) . . ?
C20 N2 C19 124.85(12) . . ?
N1 C1 H1 106.8 . . ?
N1 C1 C2 109.33(10) . . ?
N1 C1 C16 114.23(10) . . ?
C2 C1 H1 106.8 . . ?
C2 C1 C16 112.54(10) . . ?
C16 C1 H1 106.8 . . ?
C3 C2 C1 118.76(12) . . ?
C3 C2 C7 119.73(12) . . ?
C7 C2 C1 121.51(12) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.97(14) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.45(15) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.12(14) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.29(14) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 118.43(13) . . ?
C2 C7 C8 121.31(12) . . ?
C6 C7 C8 120.25(13) . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C7 C8 C9 112.94(11) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
N1 C9 C8 108.71(11) . . ?
N1 C9 H9A 109.9 . . ?
N1 C9 H9B 109.9 . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C11 C10 N1 118.58(13) . . ?
C15 C10 N1 122.98(13) . . ?
C15 C10 C11 118.42(14) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.51(18) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.32(19) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.36(17) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.11(18) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C14 120.26(17) . . ?
C10 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C1 124.43(11) . . ?
C17 C16 C25 106.67(11) . . ?
C25 C16 C1 128.86(11) . . ?
N2 C17 C18 119.60(11) . . ?
C16 C17 N2 109.59(11) . . ?
C16 C17 C18 130.80(12) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C20 C21 129.40(12) . . ?
N2 C20 C25 107.79(11) . . ?
C21 C20 C25 122.82(12) . . ?
C20 C21 H21 121.1 . . ?
C22 C21 C20 117.78(13) . . ?
C22 C21 H21 121.1 . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 120.96(13) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.15(14) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.84(13) . . ?
C25 C24 H24 120.1 . . ?
C20 C25 C16 106.83(11) . . ?
C24 C25 C16 135.73(12) . . ?
C24 C25 C20 117.40(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 159.81(11) . . . . ?
N1 C1 C2 C7 -20.02(16) . . . . ?
N1 C1 C16 C17 -92.34(14) . . . . ?
N1 C1 C16 C25 85.20(15) . . . . ?
N1 C10 C11 C12 179.94(14) . . . . ?
N1 C10 C15 C14 -178.65(14) . . . . ?
N2 C20 C21 C22 -177.84(13) . . . . ?
N2 C20 C25 C16 -1.15(14) . . . . ?
N2 C20 C25 C24 176.96(11) . . . . ?
C1 N1 C9 C8 -67.85(14) . . . . ?
C1 N1 C10 C11 72.18(15) . . . . ?
C1 N1 C10 C15 -109.35(14) . . . . ?
C1 C2 C3 C4 -179.16(13) . . . . ?
C1 C2 C7 C6 -179.56(12) . . . . ?
C1 C2 C7 C8 1.6(2) . . . . ?
C1 C16 C17 N2 176.64(11) . . . . ?
C1 C16 C17 C18 -4.5(2) . . . . ?
C1 C16 C25 C20 -176.34(12) . . . . ?
C1 C16 C25 C24 6.1(2) . . . . ?
C2 C1 C16 C17 142.23(12) . . . . ?
C2 C1 C16 C25 -40.23(17) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C2 C7 C8 C9 -14.0(2) . . . . ?
C3 C2 C7 C6 0.6(2) . . . . ?
C3 C2 C7 C8 -178.27(13) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C2 -1.3(2) . . . . ?
C5 C6 C7 C8 177.54(15) . . . . ?
C6 C7 C8 C9 167.14(14) . . . . ?
C7 C2 C3 C4 0.7(2) . . . . ?
C7 C8 C9 N1 45.08(17) . . . . ?
C9 N1 C1 C2 53.78(13) . . . . ?
C9 N1 C1 C16 -73.34(13) . . . . ?
C9 N1 C10 C11 -154.16(13) . . . . ?
C9 N1 C10 C15 24.31(18) . . . . ?
C10 N1 C1 C2 -170.66(10) . . . . ?
C10 N1 C1 C16 62.22(14) . . . . ?
C10 N1 C9 C8 157.90(12) . . . . ?
C10 C11 C12 C13 -1.6(3) . . . . ?
C11 C10 C15 C14 -0.2(2) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C10 -0.9(3) . . . . ?
C15 C10 C11 C12 1.4(2) . . . . ?
C16 C1 C2 C3 -72.13(15) . . . . ?
C16 C1 C2 C7 108.04(13) . . . . ?
C17 N2 C20 C21 -179.92(13) . . . . ?
C17 N2 C20 C25 0.34(14) . . . . ?
C17 C16 C25 C20 1.54(14) . . . . ?
C17 C16 C25 C24 -176.06(15) . . . . ?
C19 N2 C17 C16 176.54(13) . . . . ?
C19 N2 C17 C18 -2.5(2) . . . . ?
C19 N2 C20 C21 4.2(2) . . . . ?
C19 N2 C20 C25 -175.59(13) . . . . ?
C20 N2 C17 C16 0.67(15) . . . . ?
C20 N2 C17 C18 -178.36(12) . . . . ?
C20 C21 C22 C23 0.2(2) . . . . ?
C21 C20 C25 C16 179.08(12) . . . . ?
C21 C20 C25 C24 -2.81(19) . . . . ?
C21 C22 C23 C24 -1.3(2) . . . . ?
C22 C23 C24 C25 0.3(2) . . . . ?
C23 C24 C25 C16 179.05(14) . . . . ?
C23 C24 C25 C20 1.6(2) . . . . ?
C25 C16 C17 N2 -1.36(14) . . . . ?
C25 C16 C17 C18 177.52(13) . . . . ?
C25 C20 C21 C22 1.9(2) . . . . ?

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

data_20221102_3O
_database_code_depnum_ccdc_archive 'CCDC 2220117'
loop_
_audit_author_name
_audit_author_address
zhang
;Shanghai University of Traditional Chinese Medicine
China
;
_audit_update_record             
;
2022-11-16 deposited with the CCDC.	2023-04-05 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         380.43

_chemical_melting_point          ?

_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   14.6228(3)
_cell_length_b                   12.8248(3)
_cell_length_c                   20.8582(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3911.63(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4845
_cell_measurement_theta_min      4.2392
_cell_measurement_theta_max      59.8259
_cell_measurement_temperature    273.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600

_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      273.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             0.06
_diffrn_source_current           1.1
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'cu k\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'd8 venture'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            35113
_diffrn_reflns_av_R_equivalents  0.1160
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_theta_min         4.24
_diffrn_reflns_theta_max         65.20
_diffrn_reflns_theta_full        65.20
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
;

_reflns_number_total             3335
_reflns_number_gt                2282
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1499
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_number_reflns         3335
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0889P)²+0.2313P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1230)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.35888(11) 0.32248(13) 0.64010(8) 0.0660(5) Uani d . . . 1 . .
O O2 0.37060(11) 0.40712(15) 0.73288(8) 0.0720(5) Uani d . . . 1 . .
N N1 0.70322(13) 0.37162(16) 0.69427(10) 0.0593(5) Uani d . . . 1 . .
H H19 0.755(2) 0.382(2) 0.7134(14) 0.089000 Uiso d U . . 1 . .
N N2 0.46454(15) 0.72353(16) 0.70979(10) 0.0647(6) Uani d . . . 1 . .
H H1B 0.454(2) 0.769(2) 0.7412(15) 0.097000 Uiso d U . . 1 . .
C C1 0.2551(3) 0.0001(3) 0.53885(18) 0.1006(12) Uani d . . . 1 . .
H H1 0.246272 -0.055876 0.511197 0.121000 Uiso calc U . R 1 . .
C C2 0.3210(3) -0.0058(3) 0.5846(2) 0.1060(11) Uani d . . . 1 . .
H H16 0.358175 -0.064406 0.587365 0.127000 Uiso calc U . R 1 . .
C C3 0.3324(2) 0.0761(3) 0.62698(17) 0.0941(10) Uani d . . . 1 . .
H H17 0.376964 0.072031 0.658668 0.113000 Uiso calc U . R 1 . .
C C4 0.27779(19) 0.1642(2) 0.62260(14) 0.0733(8) Uani d . . . 1 . .
C C5 0.2908(2) 0.2526(2) 0.66808(15) 0.0926(10) Uani d . . . 1 . .
H H4 0.233559 0.289295 0.674481 0.111000 Uiso calc U . R 1 . .
H H5 0.311927 0.226915 0.709248 0.111000 Uiso calc U . R 1 . .
C C6 0.39444(14) 0.39478(18) 0.67817(11) 0.0501(5) Uani d . . . 1 . .
C C7 0.47085(13) 0.45304(17) 0.64485(10) 0.0454(5) Uani d . . . 1 . .
H H15 0.460084 0.447843 0.598583 0.055000 Uiso calc U . R 1 . .
C C8 0.47377(13) 0.56748(16) 0.66172(10) 0.0467(5) Uani d . . . 1 . .
C C9 0.51604(13) 0.64398(16) 0.62159(10) 0.0459(5) Uani d . . . 1 . .
C C10 0.50929(15) 0.74091(18) 0.65275(11) 0.0538(6) Uani d . . . 1 . .
C C11 0.54443(18) 0.83167(19) 0.62666(13) 0.0668(7) Uani d . . . 1 . .
H H13 0.539173 0.895215 0.647826 0.080000 Uiso calc U . R 1 . .
C C12 0.5876(2) 0.8242(2) 0.56800(13) 0.0718(7) Uani d . . . 1 . .
H H2 0.612271 0.883789 0.549424 0.086000 Uiso calc U . R 1 . .
C C13 0.2017(2) 0.0863(3) 0.53275(17) 0.0968(10) Uani d . . . 1 . .
H H18 0.158053 0.090322 0.500398 0.116000 Uiso calc U . R 1 . .
C C14 0.2131(2) 0.1682(2) 0.57538(16) 0.0867(9) Uani d . . . 1 . .
H H3 0.176110 0.226883 0.571787 0.104000 Uiso calc U . R 1 . .
C C15 0.56075(13) 0.39915(17) 0.65899(10) 0.0456(5) Uani d . . . 1 . .
C C16 0.59021(14) 0.29718(17) 0.63832(9) 0.0475(5) Uani d . . . 1 . .
C C17 0.68000(14) 0.28284(18) 0.66173(10) 0.0501(5) Uani d . . . 1 . .
C C18 0.63210(14) 0.44045(18) 0.69281(11) 0.0523(5) Uani d . . . 1 . .
H H6 0.632173 0.505890 0.712025 0.063000 Uiso calc U . R 1 . .
C C19 0.72885(17) 0.1916(2) 0.65155(11) 0.0635(6) Uani d . . . 1 . .
H H7 0.787992 0.183759 0.667228 0.076000 Uiso calc U . R 1 . .
C C20 0.68722(19) 0.1137(2) 0.61775(13) 0.0721(7) Uani d . . . 1 . .
H H8 0.718074 0.051290 0.611016 0.087000 Uiso calc U . R 1 . .
C C21 0.59956(19) 0.1263(2) 0.59327(13) 0.0751(8) Uani d . . . 1 . .
H H9 0.573223 0.072241 0.569967 0.090000 Uiso calc U . R 1 . .
C C22 0.55086(16) 0.2165(2) 0.60264(11) 0.0609(6) Uani d . . . 1 . .
H H10 0.492509 0.223922 0.585494 0.073000 Uiso calc U . R 1 . .
C C23 0.59493(18) 0.7292(2) 0.53607(11) 0.0651(7) Uani d . . . 1 . .
H H12 0.624445 0.726593 0.496615 0.078000 Uiso calc U . R 1 . .
C C24 0.55928(15) 0.63929(18) 0.56186(10) 0.0538(6) Uani d . . . 1 . .
H H11 0.563873 0.576369 0.539936 0.065000 Uiso calc U . R 1 . .
C C25 0.44397(16) 0.61930(19) 0.71505(11) 0.0584(6) Uani d . . . 1 . .
H H14 0.414255 0.588643 0.749674 0.070000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C6 . 1.327(3) ?
O1 C5 . 1.460(3) ?
O2 C6 . 1.204(3) ?
N1 C18 . 1.365(3) ?
N1 C17 . 1.368(3) ?
N1 H19 . 0.87(3) ?
N2 C25 . 1.375(3) ?
N2 C10 . 1.376(3) ?
N2 H1B . 0.89(3) ?
C1 C2 . 1.358(5) ?
C1 C13 . 1.359(5) ?
C1 H1 . 0.930000 ?
C2 C3 . 1.383(5) ?
C2 H16 . 0.930000 ?
C3 C4 . 1.387(4) ?
C3 H17 . 0.930000 ?
C4 C14 . 1.366(4) ?
C4 C5 . 1.491(4) ?
C5 H4 . 0.970000 ?
C5 H5 . 0.970000 ?
C6 C7 . 1.513(3) ?
C7 C8 . 1.510(3) ?
C7 C15 . 1.514(3) ?
C7 H15 . 0.980000 ?
C8 C25 . 1.367(3) ?
C8 C9 . 1.430(3) ?
C9 C24 . 1.398(3) ?
C9 C10 . 1.406(3) ?
C10 C11 . 1.384(3) ?
C11 C12 . 1.380(4) ?
C11 H13 . 0.930000 ?
C12 C23 . 1.392(4) ?
C12 H2 . 0.930000 ?
C13 C14 . 1.386(4) ?
C13 H18 . 0.930000 ?
C14 H3 . 0.930000 ?
C15 C18 . 1.366(3) ?
C15 C16 . 1.443(3) ?
C16 C22 . 1.398(3) ?
C16 C17 . 1.413(3) ?
C17 C19 . 1.387(3) ?
C18 H6 . 0.930000 ?
C19 C20 . 1.366(4) ?
C19 H7 . 0.930000 ?
C20 C21 . 1.389(4) ?
C20 H8 . 0.930000 ?
C21 C22 . 1.373(4) ?
C21 H9 . 0.930000 ?
C22 H10 . 0.930000 ?
C23 C24 . 1.375(3) ?
C23 H12 . 0.930000 ?
C24 H11 . 0.930000 ?
C25 H14 . 0.930000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 O1 C5 . . 117.16(19) ?
C18 N1 C17 . . 109.76(18) ?
C18 N1 H19 . . 125.(2) ?
C17 N1 H19 . . 125.(2) ?
C25 N2 C10 . . 109.30(19) ?
C25 N2 H1B . . 123.(2) ?
C10 N2 H1B . . 128.(2) ?
C2 C1 C13 . . 121.2(3) ?
C2 C1 H1 . . 119.400000 ?
C13 C1 H1 . . 119.400000 ?
C1 C2 C3 . . 119.5(4) ?
C1 C2 H16 . . 120.200000 ?
C3 C2 H16 . . 120.200000 ?
C2 C3 C4 . . 120.5(3) ?
C2 C3 H17 . . 119.800000 ?
C4 C3 H17 . . 119.800000 ?
C14 C4 C3 . . 118.4(3) ?
C14 C4 C5 . . 121.3(3) ?
C3 C4 C5 . . 120.3(3) ?
O1 C5 C4 . . 107.4(2) ?
O1 C5 H4 . . 110.200000 ?
C4 C5 H4 . . 110.200000 ?
O1 C5 H5 . . 110.200000 ?
C4 C5 H5 . . 110.200000 ?
H4 C5 H5 . . 108.500000 ?
O2 C6 O1 . . 123.1(2) ?
O2 C6 C7 . . 125.8(2) ?
O1 C6 C7 . . 111.07(18) ?
C8 C7 C6 . . 113.19(17) ?
C8 C7 C15 . . 111.94(17) ?
C6 C7 C15 . . 109.03(17) ?
C8 C7 H15 . . 107.500000 ?
C6 C7 H15 . . 107.500000 ?
C15 C7 H15 . . 107.500000 ?
C25 C8 C9 . . 106.29(19) ?
C25 C8 C7 . . 130.8(2) ?
C9 C8 C7 . . 122.87(18) ?
C24 C9 C10 . . 118.8(2) ?
C24 C9 C8 . . 133.4(2) ?
C10 C9 C8 . . 107.79(18) ?
N2 C10 C11 . . 130.7(2) ?
N2 C10 C9 . . 106.8(2) ?
C11 C10 C9 . . 122.4(2) ?
C12 C11 C10 . . 117.4(2) ?
C12 C11 H13 . . 121.300000 ?
C10 C11 H13 . . 121.300000 ?
C11 C12 C23 . . 121.4(2) ?
C11 C12 H2 . . 119.300000 ?
C23 C12 H2 . . 119.300000 ?
C1 C13 C14 . . 119.1(3) ?
C1 C13 H18 . . 120.400000 ?
C14 C13 H18 . . 120.400000 ?
C4 C14 C13 . . 121.2(3) ?
C4 C14 H3 . . 119.400000 ?
C13 C14 H3 . . 119.400000 ?
C18 C15 C16 . . 106.12(18) ?
C18 C15 C7 . . 125.9(2) ?
C16 C15 C7 . . 127.93(18) ?
C22 C16 C17 . . 118.0(2) ?
C22 C16 C15 . . 135.0(2) ?
C17 C16 C15 . . 106.99(19) ?
N1 C17 C19 . . 130.5(2) ?
N1 C17 C16 . . 107.09(19) ?
C19 C17 C16 . . 122.4(2) ?
N1 C18 C15 . . 110.0(2) ?
N1 C18 H6 . . 125.000000 ?
C15 C18 H6 . . 125.000000 ?
C20 C19 C17 . . 117.8(2) ?
C20 C19 H7 . . 121.100000 ?
C17 C19 H7 . . 121.100000 ?
C19 C20 C21 . . 121.1(2) ?
C19 C20 H8 . . 119.500000 ?
C21 C20 H8 . . 119.500000 ?
C22 C21 C20 . . 121.6(3) ?
C22 C21 H9 . . 119.200000 ?
C20 C21 H9 . . 119.200000 ?
C21 C22 C16 . . 119.1(2) ?
C21 C22 H10 . . 120.500000 ?
C16 C22 H10 . . 120.500000 ?
C24 C23 C12 . . 121.2(2) ?
C24 C23 H12 . . 119.400000 ?
C12 C23 H12 . . 119.400000 ?
C23 C24 C9 . . 118.9(2) ?
C23 C24 H11 . . 120.500000 ?
C9 C24 H11 . . 120.500000 ?
C8 C25 N2 . . 109.8(2) ?
C8 C25 H14 . . 125.100000 ?
N2 C25 H14 . . 125.100000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C13 C1 C2 C3 . . . . 1.9(5) ?
C1 C2 C3 C4 . . . . -0.7(5) ?
C2 C3 C4 C14 . . . . -0.3(4) ?
C2 C3 C4 C5 . . . . -179.5(3) ?
C6 O1 C5 C4 . . . . -166.6(2) ?
C14 C4 C5 O1 . . . . -90.4(3) ?
C3 C4 C5 O1 . . . . 88.8(3) ?
C5 O1 C6 O2 . . . . -2.9(4) ?
C5 O1 C6 C7 . . . . 173.7(2) ?
O2 C6 C7 C8 . . . . -40.1(3) ?
O1 C6 C7 C8 . . . . 143.36(19) ?
O2 C6 C7 C15 . . . . 85.2(3) ?
O1 C6 C7 C15 . . . . -91.3(2) ?
C6 C7 C8 C25 . . . . 25.9(3) ?
C15 C7 C8 C25 . . . . -97.9(3) ?
C6 C7 C8 C9 . . . . -157.44(19) ?
C15 C7 C8 C9 . . . . 78.8(2) ?
C25 C8 C9 C24 . . . . 179.5(2) ?
C7 C8 C9 C24 . . . . 2.1(4) ?
C25 C8 C9 C10 . . . . -0.4(2) ?
C7 C8 C9 C10 . . . . -177.82(19) ?
C25 N2 C10 C11 . . . . -179.0(3) ?
C25 N2 C10 C9 . . . . 0.4(3) ?
C24 C9 C10 N2 . . . . -179.88(19) ?
C8 C9 C10 N2 . . . . 0.0(2) ?
C24 C9 C10 C11 . . . . -0.4(3) ?
C8 C9 C10 C11 . . . . 179.5(2) ?
N2 C10 C11 C12 . . . . 179.0(2) ?
C9 C10 C11 C12 . . . . -0.3(4) ?
C10 C11 C12 C23 . . . . 0.5(4) ?
C2 C1 C13 C14 . . . . -2.0(5) ?
C3 C4 C14 C13 . . . . 0.2(4) ?
C5 C4 C14 C13 . . . . 179.4(3) ?
C1 C13 C14 C4 . . . . 1.0(5) ?
C8 C7 C15 C18 . . . . 10.8(3) ?
C6 C7 C15 C18 . . . . -115.3(2) ?
C8 C7 C15 C16 . . . . -166.90(19) ?
C6 C7 C15 C16 . . . . 67.1(3) ?
C18 C15 C16 C22 . . . . -179.8(2) ?
C7 C15 C16 C22 . . . . -1.8(4) ?
C18 C15 C16 C17 . . . . 0.1(2) ?
C7 C15 C16 C17 . . . . 178.12(19) ?
C18 N1 C17 C19 . . . . -178.6(2) ?
C18 N1 C17 C16 . . . . 0.5(2) ?
C22 C16 C17 N1 . . . . 179.57(19) ?
C15 C16 C17 N1 . . . . -0.4(2) ?
C22 C16 C17 C19 . . . . -1.3(3) ?
C15 C16 C17 C19 . . . . 178.8(2) ?
C17 N1 C18 C15 . . . . -0.4(3) ?
C16 C15 C18 N1 . . . . 0.2(2) ?
C7 C15 C18 N1 . . . . -177.88(19) ?
N1 C17 C19 C20 . . . . 178.7(2) ?
C16 C17 C19 C20 . . . . -0.2(3) ?
C17 C19 C20 C21 . . . . 1.3(4) ?
C19 C20 C21 C22 . . . . -0.8(4) ?
C20 C21 C22 C16 . . . . -0.7(4) ?
C17 C16 C22 C21 . . . . 1.7(3) ?
C15 C16 C22 C21 . . . . -178.4(2) ?
C11 C12 C23 C24 . . . . 0.1(4) ?
C12 C23 C24 C9 . . . . -0.8(4) ?
C10 C9 C24 C23 . . . . 1.0(3) ?
C8 C9 C24 C23 . . . . -179.0(2) ?
C9 C8 C25 N2 . . . . 0.7(3) ?
C7 C8 C25 N2 . . . . 177.8(2) ?
C10 N2 C25 C8 . . . . -0.6(3) ?

