# 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. 
# 
#######################################################################

data_mo_220525c_0m
_database_code_depnum_ccdc_archive 'CCDC 2264899'
loop_
_audit_author_name
_audit_author_address
'Yu ZhiCheng'
;Central China Normal University
China
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2023-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-05-26
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 N4 O2'
_chemical_formula_sum            'C23 H16 N4 O2'
_chemical_formula_weight         380.40
_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 0.0033 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.378(4)
_cell_length_b                   28.538(12)
_cell_length_c                   14.882(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.505(7)
_cell_angle_gamma                90
_cell_volume                     3964(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2860
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      25.38
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1366
_diffrn_reflns_av_unetI/netI     0.1319
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29945
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.426
_diffrn_reflns_theta_min         1.427
_diffrn_ambient_temperature      296(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3299
_reflns_number_total             7930
_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         7930
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1953
_refine_ls_R_factor_gt           0.0732
_refine_ls_restrained_S_all      0.977
_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)+(0.0908P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.2136
_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 Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C19(H19), C20(H20), C21(H21), 
 C22(H22), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C42(H42), 
  C43(H43), C44(H44), C45(H45), C46(H46) 
2.b Idealised Me refined as rotating group: 
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C37(H37A,H37B,H37C), C38(H38A,H38B, 
 H38C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7429(3) 0.57460(9) -0.01132(18) 0.0698(9) Uani 1 1 d . . . . .
O2 O 0.6050(5) 0.36682(13) -0.0650(2) 0.1138(15) Uani 1 1 d . . . . .
O3 O 0.7558(4) 0.43919(11) 0.2693(2) 0.0989(12) Uani 1 1 d . . . . .
O4 O 1.0759(4) 0.29687(12) 0.4871(2) 0.0875(10) Uani 1 1 d . . . . .
N1 N 0.9168(3) 0.48419(10) 0.10609(18) 0.0431(7) Uani 1 1 d . . . . .
N2 N 1.0365(4) 0.41289(11) 0.1471(2) 0.0549(9) Uani 1 1 d . . . . .
N3 N 1.0364(4) 0.36756(12) 0.1186(3) 0.0650(10) Uani 1 1 d . . . . .
N4 N 0.5220(5) 0.50695(14) -0.1240(3) 0.0805(12) Uani 1 1 d . . . . .
N5 N 0.9119(4) 0.27220(11) 0.2802(2) 0.0536(9) Uani 1 1 d . . . . .
N6 N 0.7319(4) 0.25891(12) 0.1584(2) 0.0584(9) Uani 1 1 d . . . . .
N7 N 0.6165(4) 0.28242(13) 0.1157(2) 0.0621(9) Uani 1 1 d . . . . .
N8 N 0.9693(5) 0.40669(15) 0.4757(3) 0.0929(14) Uani 1 1 d . . . . .
C1 C 0.8048(4) 0.57657(12) 0.1453(3) 0.0448(9) Uani 1 1 d . . . . .
C2 C 0.7987(4) 0.55350(13) 0.2263(2) 0.0494(10) Uani 1 1 d . . . . .
H2 H 0.7800 0.5215 0.2266 0.059 Uiso 1 1 calc R . . . .
C3 C 0.8200(5) 0.57745(15) 0.3066(3) 0.0662(12) Uani 1 1 d . . . . .
H3 H 0.8145 0.5617 0.3609 0.079 Uiso 1 1 calc R . . . .
C4 C 0.8494(5) 0.62481(18) 0.3067(3) 0.0759(14) Uani 1 1 d . . . . .
H4 H 0.8669 0.6409 0.3610 0.091 Uiso 1 1 calc R . . . .
C5 C 0.8530(5) 0.64816(15) 0.2265(4) 0.0738(14) Uani 1 1 d . . . . .
H5 H 0.8707 0.6802 0.2265 0.089 Uiso 1 1 calc R . . . .
C6 C 0.8306(4) 0.62459(14) 0.1467(3) 0.0607(11) Uani 1 1 d . . . . .
H6 H 0.8327 0.6408 0.0926 0.073 Uiso 1 1 calc R . . . .
C7 C 0.7828(4) 0.55299(13) 0.0566(3) 0.0459(9) Uani 1 1 d . . . . .
C8 C 0.8135(4) 0.50143(13) 0.0484(2) 0.0428(9) Uani 1 1 d . . . . .
C9 C 0.7356(4) 0.47445(13) -0.0202(2) 0.0444(9) Uani 1 1 d . . . . .
C10 C 0.7656(4) 0.42737(13) -0.0293(2) 0.0456(10) Uani 1 1 d . . . . .
C11 C 0.8731(4) 0.40807(13) 0.0299(2) 0.0462(10) Uani 1 1 d . . . . .
C12 C 0.9411(4) 0.43858(13) 0.0954(2) 0.0429(9) Uani 1 1 d . . . . .
C13 C 0.9392(5) 0.36393(14) 0.0496(3) 0.0584(11) Uani 1 1 d . . . . .
C14 C 0.9141(6) 0.31841(14) 0.0009(3) 0.0825(15) Uani 1 1 d . . . . .
H14A H 0.9303 0.3224 -0.0614 0.124 Uiso 1 1 calc GR . . . .
H14B H 0.8171 0.3084 0.0049 0.124 Uiso 1 1 calc GR . . . .
H14C H 0.9787 0.2952 0.0279 0.124 Uiso 1 1 calc GR . . . .
C15 C 1.1362(5) 0.42829(16) 0.2203(3) 0.0715(13) Uani 1 1 d . . . . .
H15A H 1.1430 0.4051 0.2672 0.107 Uiso 1 1 calc GR . . . .
H15B H 1.1037 0.4573 0.2437 0.107 Uiso 1 1 calc GR . . . .
H15C H 1.2286 0.4328 0.1989 0.107 Uiso 1 1 calc GR . . . .
C16 C 0.6181(5) 0.49453(15) -0.0774(3) 0.0571(11) Uani 1 1 d . . . . .
C17 C 0.6761(5) 0.39702(15) -0.0959(3) 0.0606(12) Uani 1 1 d . . . . .
C18 C 0.6780(4) 0.40442(13) -0.1927(2) 0.0483(10) Uani 1 1 d . . . . .
C19 C 0.5608(5) 0.38830(15) -0.2496(3) 0.0650(12) Uani 1 1 d . . . . .
H19 H 0.4836 0.3742 -0.2254 0.078 Uiso 1 1 calc R . . . .
C20 C 0.5605(6) 0.39328(18) -0.3398(3) 0.0796(14) Uani 1 1 d . . . . .
H20 H 0.4814 0.3835 -0.3776 0.095 Uiso 1 1 calc R . . . .
C21 C 0.6749(7) 0.41254(17) -0.3759(3) 0.0783(15) Uani 1 1 d . . . . .
H21 H 0.6739 0.4150 -0.4383 0.094 Uiso 1 1 calc R . . . .
C22 C 0.7913(6) 0.42840(16) -0.3222(3) 0.0732(13) Uani 1 1 d . . . . .
H22 H 0.8691 0.4414 -0.3474 0.088 Uiso 1 1 calc R . . . .
C23 C 0.7912(5) 0.42473(14) -0.2290(3) 0.0557(11) Uani 1 1 d . . . . .
H23 H 0.8684 0.4361 -0.1914 0.067 Uiso 1 1 calc R . . . .
C24 C 0.5692(4) 0.41159(13) 0.3503(2) 0.0481(10) Uani 1 1 d . . . . .
C25 C 0.5052(5) 0.37373(15) 0.3869(3) 0.0576(11) Uani 1 1 d . . . . .
H25 H 0.5427 0.3439 0.3801 0.069 Uiso 1 1 calc R . . . .
C26 C 0.3854(5) 0.37935(19) 0.4338(3) 0.0707(13) Uani 1 1 d . . . . .
H26 H 0.3428 0.3535 0.4583 0.085 Uiso 1 1 calc R . . . .
C27 C 0.3307(5) 0.4231(2) 0.4435(3) 0.0819(15) Uani 1 1 d . . . . .
H27 H 0.2504 0.4273 0.4748 0.098 Uiso 1 1 calc R . . . .
C28 C 0.3938(7) 0.4608(2) 0.4075(4) 0.0924(17) Uani 1 1 d . . . . .
H28 H 0.3566 0.4906 0.4154 0.111 Uiso 1 1 calc R . . . .
C29 C 0.5108(5) 0.45591(16) 0.3597(3) 0.0725(13) Uani 1 1 d . . . . .
H29 H 0.5506 0.4819 0.3339 0.087 Uiso 1 1 calc R . . . .
C30 C 0.6961(5) 0.40682(14) 0.3020(3) 0.0558(11) Uani 1 1 d . . . . .
C31 C 0.7645(4) 0.35922(13) 0.2951(3) 0.0481(10) Uani 1 1 d . . . . .
C32 C 0.8818(4) 0.34683(13) 0.3528(3) 0.0500(10) Uani 1 1 d . . . . .
C33 C 0.9534(4) 0.30360(14) 0.3430(3) 0.0522(10) Uani 1 1 d . . . . .
C34 C 0.7952(5) 0.28486(14) 0.2267(3) 0.0505(10) Uani 1 1 d . . . . .
C35 C 0.7183(4) 0.32666(14) 0.2288(3) 0.0504(10) Uani 1 1 d . . . . .
C36 C 0.6071(5) 0.32289(15) 0.1576(3) 0.0562(11) Uani 1 1 d . . . . .
C37 C 0.7754(6) 0.21361(15) 0.1269(3) 0.0828(15) Uani 1 1 d . . . . .
H37A H 0.6923 0.1961 0.1043 0.124 Uiso 1 1 calc GR . . . .
H37B H 0.8260 0.1968 0.1761 0.124 Uiso 1 1 calc GR . . . .
H37C H 0.8370 0.2178 0.0796 0.124 Uiso 1 1 calc GR . . . .
C38 C 0.4909(5) 0.35662(16) 0.1295(3) 0.0745(14) Uani 1 1 d . . . . .
H38A H 0.4444 0.3475 0.0719 0.112 Uiso 1 1 calc GR . . . .
H38B H 0.5308 0.3874 0.1251 0.112 Uiso 1 1 calc GR . . . .
H38C H 0.4224 0.3568 0.1735 0.112 Uiso 1 1 calc GR . . . .
C39 C 0.9334(5) 0.37965(16) 0.4221(3) 0.0640(12) Uani 1 1 d . . . . .
C40 C 1.0817(5) 0.29062(14) 0.4073(3) 0.0580(11) Uani 1 1 d . . . . .
C41 C 1.2080(4) 0.27106(13) 0.3698(3) 0.0521(10) Uani 1 1 d . . . . .
C42 C 1.3113(5) 0.24876(15) 0.4280(3) 0.0693(13) Uani 1 1 d . . . . .
H42 H 1.2975 0.2457 0.4888 0.083 Uiso 1 1 calc R . . . .
C43 C 1.4330(6) 0.23130(16) 0.3967(4) 0.0829(15) Uani 1 1 d . . . . .
H43 H 1.5022 0.2169 0.4363 0.099 Uiso 1 1 calc R . . . .
C44 C 1.4528(6) 0.23512(17) 0.3064(4) 0.0834(15) Uani 1 1 d . . . . .
H44 H 1.5348 0.2227 0.2849 0.100 Uiso 1 1 calc R . . . .
C45 C 1.3534(5) 0.25680(16) 0.2489(3) 0.0736(13) Uani 1 1 d . . . . .
H45 H 1.3675 0.2591 0.1880 0.088 Uiso 1 1 calc R . . . .
C46 C 1.2317(5) 0.27546(14) 0.2795(3) 0.0602(11) Uani 1 1 d . . . . .
H46 H 1.1653 0.2910 0.2398 0.072 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
O1 C7 1.212(4) . ?
O2 C17 1.207(5) . ?
O3 C30 1.207(4) . ?
O4 C40 1.207(5) . ?
N1 C8 1.325(4) . ?
N1 C12 1.334(4) . ?
N2 N3 1.361(4) . ?
N2 C12 1.341(5) . ?
N2 C15 1.435(5) . ?
N3 C13 1.310(5) . ?
N4 C16 1.140(5) . ?
N5 C33 1.326(5) . ?
N5 C34 1.340(5) . ?
N6 N7 1.376(5) . ?
N6 C34 1.349(5) . ?
N6 C37 1.447(5) . ?
N7 C36 1.319(5) . ?
N8 C39 1.137(5) . ?
C1 C2 1.380(5) . ?
C1 C6 1.392(5) . ?
C1 C7 1.478(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.363(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.507(5) . ?
C8 C9 1.423(5) . ?
C9 C10 1.382(5) . ?
C9 C16 1.445(6) . ?
C10 C11 1.388(5) . ?
C10 C17 1.509(5) . ?
C11 C12 1.412(5) . ?
C11 C13 1.422(5) . ?
C13 C14 1.495(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 C18 1.458(5) . ?
C18 C19 1.400(5) . ?
C18 C23 1.366(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.349(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.362(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.367(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.390(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(5) . ?
C24 C29 1.390(5) . ?
C24 C30 1.455(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.388(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.364(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.362(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.371(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.510(5) . ?
C31 C32 1.375(5) . ?
C31 C35 1.394(5) . ?
C32 C33 1.419(5) . ?
C32 C39 1.442(6) . ?
C33 C40 1.510(6) . ?
C34 C35 1.396(5) . ?
C35 C36 1.418(5) . ?
C36 C38 1.483(6) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C40 C41 1.467(6) . ?
C41 C42 1.390(6) . ?
C41 C46 1.389(5) . ?
C42 H42 0.9300 . ?
C42 C43 1.367(7) . ?
C43 H43 0.9300 . ?
C43 C44 1.379(7) . ?
C44 H44 0.9300 . ?
C44 C45 1.353(6) . ?
C45 H45 0.9300 . ?
C45 C46 1.377(6) . ?
C46 H46 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
C8 N1 C12 114.1(3) . . ?
N3 N2 C15 120.5(3) . . ?
C12 N2 N3 111.1(3) . . ?
C12 N2 C15 128.2(3) . . ?
C13 N3 N2 107.4(3) . . ?
C33 N5 C34 113.8(4) . . ?
N7 N6 C37 121.4(4) . . ?
C34 N6 N7 110.5(3) . . ?
C34 N6 C37 128.1(4) . . ?
C36 N7 N6 107.1(3) . . ?
C2 C1 C6 118.6(4) . . ?
C2 C1 C7 123.3(3) . . ?
C6 C1 C7 118.1(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.7(4) . . ?
C5 C6 H6 119.7 . . ?
O1 C7 C1 121.2(3) . . ?
O1 C7 C8 118.4(3) . . ?
C1 C7 C8 120.3(3) . . ?
N1 C8 C7 116.4(3) . . ?
N1 C8 C9 123.8(3) . . ?
C9 C8 C7 119.8(3) . . ?
C8 C9 C16 121.2(4) . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 C16 118.6(3) . . ?
C9 C10 C11 117.7(3) . . ?
C9 C10 C17 121.2(4) . . ?
C11 C10 C17 120.9(4) . . ?
C10 C11 C12 116.5(4) . . ?
C10 C11 C13 139.3(4) . . ?
C12 C11 C13 104.2(4) . . ?
N1 C12 N2 125.3(3) . . ?
N1 C12 C11 127.8(3) . . ?
N2 C12 C11 106.9(3) . . ?
N3 C13 C11 110.4(3) . . ?
N3 C13 C14 120.9(4) . . ?
C11 C13 C14 128.6(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 C9 174.8(5) . . ?
O2 C17 C10 116.9(4) . . ?
O2 C17 C18 122.7(4) . . ?
C18 C17 C10 120.4(4) . . ?
C19 C18 C17 117.8(4) . . ?
C23 C18 C17 122.5(4) . . ?
C23 C18 C19 119.7(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.6(5) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.6(5) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.4 . . ?
C20 C21 C22 121.2(4) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 H22 120.6 . . ?
C21 C22 C23 118.8(5) . . ?
C23 C22 H22 120.6 . . ?
C18 C23 C22 120.1(4) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C29 119.0(4) . . ?
C25 C24 C30 122.1(4) . . ?
C29 C24 C30 118.9(4) . . ?
C24 C25 H25 119.5 . . ?
C24 C25 C26 120.9(4) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.4(5) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 119.9(5) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 119.2 . . ?
C27 C28 C29 121.6(5) . . ?
C29 C28 H28 119.2 . . ?
C24 C29 H29 120.4 . . ?
C28 C29 C24 119.1(5) . . ?
C28 C29 H29 120.4 . . ?
O3 C30 C24 124.1(4) . . ?
O3 C30 C31 116.4(4) . . ?
C24 C30 C31 119.4(3) . . ?
C32 C31 C30 120.5(4) . . ?
C32 C31 C35 116.5(4) . . ?
C35 C31 C30 122.9(4) . . ?
C31 C32 C33 121.1(4) . . ?
C31 C32 C39 118.3(4) . . ?
C33 C32 C39 120.6(4) . . ?
N5 C33 C32 123.4(4) . . ?
N5 C33 C40 116.3(4) . . ?
C32 C33 C40 120.3(4) . . ?
N5 C34 N6 125.1(4) . . ?
N5 C34 C35 127.7(4) . . ?
N6 C34 C35 107.1(4) . . ?
C31 C35 C34 117.3(4) . . ?
C31 C35 C36 137.4(4) . . ?
C34 C35 C36 105.3(4) . . ?
N7 C36 C35 110.0(4) . . ?
N7 C36 C38 121.0(4) . . ?
C35 C36 C38 129.0(4) . . ?
N6 C37 H37A 109.5 . . ?
N6 C37 H37B 109.5 . . ?
N6 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N8 C39 C32 177.1(5) . . ?
O4 C40 C33 118.6(4) . . ?
O4 C40 C41 122.9(4) . . ?
C41 C40 C33 118.4(4) . . ?
C42 C41 C40 118.5(4) . . ?
C46 C41 C40 122.9(4) . . ?
C46 C41 C42 118.5(4) . . ?
C41 C42 H42 119.7 . . ?
C43 C42 C41 120.6(5) . . ?
C43 C42 H42 119.7 . . ?
C42 C43 H43 120.1 . . ?
C42 C43 C44 119.9(5) . . ?
C44 C43 H43 120.1 . . ?
C43 C44 H44 119.9 . . ?
C45 C44 C43 120.2(5) . . ?
C45 C44 H44 119.9 . . ?
C44 C45 H45 119.7 . . ?
C44 C45 C46 120.7(5) . . ?
C46 C45 H45 119.7 . . ?
C41 C46 H46 120.0 . . ?
C45 C46 C41 120.0(4) . . ?
C45 C46 H46 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 N1 147.6(4) . . . . ?
O1 C7 C8 C9 -30.8(5) . . . . ?
O2 C17 C18 C19 22.8(7) . . . . ?
O2 C17 C18 C23 -154.8(5) . . . . ?
O3 C30 C31 C32 78.7(5) . . . . ?
O3 C30 C31 C35 -98.3(5) . . . . ?
O4 C40 C41 C42 15.5(6) . . . . ?
O4 C40 C41 C46 -161.9(4) . . . . ?
N1 C8 C9 C10 0.3(5) . . . . ?
N1 C8 C9 C16 176.0(3) . . . . ?
N2 N3 C13 C11 0.8(4) . . . . ?
N2 N3 C13 C14 178.7(4) . . . . ?
N3 N2 C12 N1 -179.7(3) . . . . ?
N3 N2 C12 C11 0.8(4) . . . . ?
N5 C33 C40 O4 -133.7(4) . . . . ?
N5 C33 C40 C41 46.5(5) . . . . ?
N5 C34 C35 C31 -1.6(6) . . . . ?
N5 C34 C35 C36 178.9(4) . . . . ?
N6 N7 C36 C35 0.4(4) . . . . ?
N6 N7 C36 C38 -178.6(3) . . . . ?
N6 C34 C35 C31 179.7(3) . . . . ?
N6 C34 C35 C36 0.2(4) . . . . ?
N7 N6 C34 N5 -178.7(3) . . . . ?
N7 N6 C34 C35 0.1(4) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C1 C7 C8 N1 -30.8(5) . . . . ?
C1 C7 C8 C9 150.8(3) . . . . ?
C2 C1 C6 C5 1.6(6) . . . . ?
C2 C1 C7 O1 155.7(4) . . . . ?
C2 C1 C7 C8 -25.9(6) . . . . ?
C2 C3 C4 C5 2.1(7) . . . . ?
C3 C4 C5 C6 -1.5(7) . . . . ?
C4 C5 C6 C1 -0.4(7) . . . . ?
C6 C1 C2 C3 -1.0(6) . . . . ?
C6 C1 C7 O1 -23.2(6) . . . . ?
C6 C1 C7 C8 155.1(4) . . . . ?
C7 C1 C2 C3 -179.9(4) . . . . ?
C7 C1 C6 C5 -179.4(4) . . . . ?
C7 C8 C9 C10 178.5(3) . . . . ?
C7 C8 C9 C16 -5.7(5) . . . . ?
C8 N1 C12 N2 -177.7(3) . . . . ?
C8 N1 C12 C11 1.6(5) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C8 C9 C10 C17 174.5(3) . . . . ?
C9 C10 C11 C12 0.8(5) . . . . ?
C9 C10 C11 C13 178.0(4) . . . . ?
C9 C10 C17 O2 -112.9(5) . . . . ?
C9 C10 C17 C18 67.4(5) . . . . ?
C10 C11 C12 N1 -1.6(6) . . . . ?
C10 C11 C12 N2 177.8(3) . . . . ?
C10 C11 C13 N3 -177.7(4) . . . . ?
C10 C11 C13 C14 4.7(8) . . . . ?
C10 C17 C18 C19 -157.6(4) . . . . ?
C10 C17 C18 C23 24.9(6) . . . . ?
C11 C10 C17 O2 61.6(6) . . . . ?
C11 C10 C17 C18 -118.0(4) . . . . ?
C12 N1 C8 C7 -179.2(3) . . . . ?
C12 N1 C8 C9 -0.9(5) . . . . ?
C12 N2 N3 C13 -1.1(4) . . . . ?
C12 C11 C13 N3 -0.3(4) . . . . ?
C12 C11 C13 C14 -177.9(4) . . . . ?
C13 C11 C12 N1 -179.7(4) . . . . ?
C13 C11 C12 N2 -0.3(4) . . . . ?
C15 N2 N3 C13 -177.6(4) . . . . ?
C15 N2 C12 N1 -3.5(6) . . . . ?
C15 N2 C12 C11 177.1(4) . . . . ?
C16 C9 C10 C11 -176.1(3) . . . . ?
C16 C9 C10 C17 -1.4(5) . . . . ?
C17 C10 C11 C12 -173.9(3) . . . . ?
C17 C10 C11 C13 3.2(7) . . . . ?
C17 C18 C19 C20 -178.1(4) . . . . ?
C17 C18 C23 C22 176.1(4) . . . . ?
C18 C19 C20 C21 2.0(7) . . . . ?
C19 C18 C23 C22 -1.4(6) . . . . ?
C19 C20 C21 C22 -1.7(8) . . . . ?
C20 C21 C22 C23 -0.2(7) . . . . ?
C21 C22 C23 C18 1.7(6) . . . . ?
C23 C18 C19 C20 -0.4(6) . . . . ?
C24 C25 C26 C27 0.0(6) . . . . ?
C24 C30 C31 C32 -98.3(5) . . . . ?
C24 C30 C31 C35 84.7(5) . . . . ?
C25 C24 C29 C28 2.0(6) . . . . ?
C25 C24 C30 O3 -179.6(4) . . . . ?
C25 C24 C30 C31 -2.9(6) . . . . ?
C25 C26 C27 C28 -0.1(7) . . . . ?
C26 C27 C28 C29 1.1(8) . . . . ?
C27 C28 C29 C24 -2.1(7) . . . . ?
C29 C24 C25 C26 -1.0(6) . . . . ?
C29 C24 C30 O3 0.5(6) . . . . ?
C29 C24 C30 C31 177.2(4) . . . . ?
C30 C24 C25 C26 179.1(4) . . . . ?
C30 C24 C29 C28 -178.1(4) . . . . ?
C30 C31 C32 C33 -175.4(3) . . . . ?
C30 C31 C32 C39 2.5(5) . . . . ?
C30 C31 C35 C34 176.7(3) . . . . ?
C30 C31 C35 C36 -3.9(7) . . . . ?
C31 C32 C33 N5 -1.5(6) . . . . ?
C31 C32 C33 C40 -179.8(3) . . . . ?
C31 C35 C36 N7 -179.8(4) . . . . ?
C31 C35 C36 C38 -0.9(8) . . . . ?
C32 C31 C35 C34 -0.4(5) . . . . ?
C32 C31 C35 C36 179.0(4) . . . . ?
C32 C33 C40 O4 44.8(6) . . . . ?
C32 C33 C40 C41 -135.0(4) . . . . ?
C33 N5 C34 N6 -179.6(4) . . . . ?
C33 N5 C34 C35 1.9(6) . . . . ?
C33 C40 C41 C42 -164.7(4) . . . . ?
C33 C40 C41 C46 18.0(6) . . . . ?
C34 N5 C33 C32 -0.3(5) . . . . ?
C34 N5 C33 C40 178.1(3) . . . . ?
C34 N6 N7 C36 -0.3(4) . . . . ?
C34 C35 C36 N7 -0.4(4) . . . . ?
C34 C35 C36 C38 178.6(4) . . . . ?
C35 C31 C32 C33 1.7(5) . . . . ?
C35 C31 C32 C39 179.7(3) . . . . ?
C37 N6 N7 C36 -177.8(4) . . . . ?
C37 N6 C34 N5 -1.4(6) . . . . ?
C37 N6 C34 C35 177.3(4) . . . . ?
C39 C32 C33 N5 -179.4(4) . . . . ?
C39 C32 C33 C40 2.2(6) . . . . ?
C40 C41 C42 C43 -177.9(4) . . . . ?
C40 C41 C46 C45 179.2(4) . . . . ?
C41 C42 C43 C44 -1.0(7) . . . . ?
C42 C41 C46 C45 1.8(6) . . . . ?
C42 C43 C44 C45 1.1(8) . . . . ?
C43 C44 C45 C46 0.2(7) . . . . ?
C44 C45 C46 C41 -1.7(7) . . . . ?
C46 C41 C42 C43 -0.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
