# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2121564'
loop_
_audit_author_name
_audit_author_address
'Ajmal Khan' 'Xian jiaotong university'
_audit_update_record             
;
2021-11-11 deposited with the CCDC.	2021-11-29 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 N5 O3'
_chemical_formula_sum            'C12 H13 N5 O3'
_chemical_formula_weight         275.27
_chemical_absolute_configuration ad
_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'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.1821(8)
_cell_length_b                   7.4470(8)
_cell_length_c                   13.2850(15)
_cell_angle_alpha                74.024(5)
_cell_angle_beta                 75.318(5)
_cell_angle_gamma                83.089(5)
_cell_volume                     659.82(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5063
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      59.920
_cell_measurement_theta_min      5.383
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1248 before and 0.0751 after correction.
The Ratio of minimum to maximum transmission is 0.8059.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8286
_diffrn_reflns_point_group_measured_fraction_full 0.799
_diffrn_reflns_point_group_measured_fraction_max 0.742
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.332
_diffrn_reflns_theta_min         5.383
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.554
_reflns_Friedel_fraction_full    0.608
_reflns_Friedel_fraction_max     0.529
_reflns_number_gt                3773
_reflns_number_total             4465
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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         0.329
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 1200 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4465
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0650
_refine_ls_restrained_S_all      1.103
_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)+(0.0900P)²+0.6683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2087
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C15(H15), C17(H17), C14(H14), C23(H23), C9(H9), C3(H3A), C6(H6A),
 C18(H18), C5(H5)
2.c X=CH2 refined with riding coordinates:
 C24(H24A,H24B), C10(H10A,H10B)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C11(H11A,H11B,H11C)
2.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O3(H3)
;
_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
N7 N 0.7768(9) -0.0535(8) 0.5632(5) 0.0411(15) Uani 1 1 d . . . . .
N2 N 0.2405(9) 1.0324(9) 0.3129(5) 0.0405(15) Uani 1 1 d . . . . .
C7 C 0.2359(10) 1.0253(11) 0.4140(6) 0.0379(17) Uani 1 1 d . . . . .
N3 N 0.2301(8) 1.2141(9) 0.2707(5) 0.0393(14) Uani 1 1 d . . . . .
O6 O 0.3970(7) -0.1321(9) 0.8740(5) 0.0508(14) Uani 1 1 d . . . . .
H6 H 0.363968 -0.037404 0.829417 0.076 Uiso 1 1 calc R U . . .
O2 O 0.3639(10) 0.3612(9) 0.8156(5) 0.0600(15) Uani 1 1 d . . . . .
O1 O 0.2780(10) 0.2023(8) 0.7229(5) 0.0571(15) Uani 1 1 d . . . . .
N4 N 0.2173(9) 1.3126(9) 0.3417(5) 0.0407(14) Uani 1 1 d . . . . .
O3 O 0.5941(8) 1.2664(9) 0.1333(5) 0.0523(14) Uani 1 1 d . . . . .
H3 H 0.644109 1.166062 0.165316 0.078 Uiso 1 1 calc R U . . .
C2 C 0.2450(10) 0.5130(12) 0.5598(6) 0.0415(18) Uani 1 1 d . . . . .
H2 H 0.227943 0.395699 0.548883 0.050 Uiso 1 1 calc R U . . .
C15 C 0.7040(11) 0.2847(11) 0.4055(6) 0.0409(17) Uani 1 1 d . . . . .
H15 H 0.688790 0.167432 0.393955 0.049 Uiso 1 1 calc R U . . .
O5 O 0.6921(9) 0.9363(9) 0.2893(5) 0.0550(14) Uani 1 1 d . . . . .
C16 C 0.7437(9) 0.2938(10) 0.5024(6) 0.0334(15) Uani 1 1 d . . . . .
C17 C 0.7650(9) 0.4618(9) 0.5218(6) 0.0348(15) Uani 1 1 d . . . . .
H17 H 0.790440 0.465133 0.588060 0.042 Uiso 1 1 calc R U . . .
C1 C 0.2874(9) 0.5240(11) 0.6547(6) 0.0352(15) Uani 1 1 d . . . . .
C20 C 0.7501(9) -0.1744(12) 0.8427(6) 0.0406(17) Uani 1 1 d . . . . .
C14 C 0.6871(11) 0.4502(11) 0.3264(6) 0.0419(17) Uani 1 1 d . . . . .
H14 H 0.661119 0.449198 0.259920 0.050 Uiso 1 1 calc R U . . .
N6 N 0.6910(9) 0.7906(10) 0.2651(6) 0.0456(16) Uani 1 1 d . . . . .
N1 N 0.3122(9) 0.3525(9) 0.7353(5) 0.0440(15) Uani 1 1 d . . . . .
N8 N 0.7803(9) -0.1829(10) 0.6561(5) 0.0461(16) Uani 1 1 d . . . . .
C21 C 0.5604(10) -0.0944(12) 0.9043(6) 0.0424(17) Uani 1 1 d . . . . .
H21A H 0.546472 -0.149339 0.982510 0.051 Uiso 1 1 calc R U . . .
H21B H 0.566760 0.042614 0.890278 0.051 Uiso 1 1 calc R U . . .
C22 C 0.9171(11) -0.1166(16) 0.8738(7) 0.060(2) Uani 1 1 d . . . . .
H22A H 0.911088 0.019897 0.860299 0.090 Uiso 1 1 calc R U . . .
H22B H 1.038368 -0.158270 0.830896 0.090 Uiso 1 1 calc R U . . .
H22C H 0.910401 -0.173840 0.950336 0.090 Uiso 1 1 calc R U . . .
C23 C 0.7389(12) -0.3814(13) 0.8575(7) 0.0495(19) Uani 1 1 d . . . . .
H23 H 0.635459 -0.421822 0.838099 0.059 Uiso 1 1 calc R U . . .
N9 N 0.7635(8) -0.0854(9) 0.7267(5) 0.0348(13) Uani 1 1 d . . . . .
C12 C 0.4408(11) 1.2262(13) 0.0954(7) 0.0460(18) Uani 1 1 d . . . . .
H12A H 0.438855 1.089178 0.107408 0.055 Uiso 1 1 calc R U . . .
H12B H 0.462456 1.283474 0.017007 0.055 Uiso 1 1 calc R U . . .
O4 O 0.6737(11) 0.7783(10) 0.1784(5) 0.0686(19) Uani 1 1 d . . . . .
N10 N 0.7472(9) 0.1016(8) 0.6882(5) 0.0390(14) Uani 1 1 d . . . . .
C13 C 0.7100(10) 0.6162(11) 0.3493(6) 0.0383(16) Uani 1 1 d . . . . .
C8 C 0.2455(11) 1.3006(11) 0.1524(6) 0.0417(16) Uani 1 1 d . . . . .
C9 C 0.0794(12) 1.2358(13) 0.1225(6) 0.0507(19) Uani 1 1 d . . . . .
H9 H -0.041877 1.300238 0.140431 0.061 Uiso 1 1 calc R U . . .
C3 C 0.2287(10) 0.6750(11) 0.4830(6) 0.0414(17) Uani 1 1 d . . . . .
H3A H 0.200057 0.669005 0.418089 0.050 Uiso 1 1 calc R U . . .
C6 C 0.3131(11) 0.6950(11) 0.6703(6) 0.0401(17) Uani 1 1 d . . . . .
H6A H 0.343982 0.700966 0.734662 0.048 Uiso 1 1 calc R U . . .
C18 C 0.7485(10) 0.6277(10) 0.4424(6) 0.0371(16) Uani 1 1 d . . . . .
H18 H 0.763934 0.745411 0.453237 0.045 Uiso 1 1 calc R U . . .
C11 C 0.2372(14) 1.5110(13) 0.1313(7) 0.053(2) Uani 1 1 d . . . . .
H11A H 0.348561 1.548514 0.149196 0.079 Uiso 1 1 calc R U . . .
H11B H 0.118155 1.552915 0.175885 0.079 Uiso 1 1 calc R U . . .
H11C H 0.239667 1.568105 0.055161 0.079 Uiso 1 1 calc R U . . .
C4 C 0.2527(9) 0.8501(12) 0.4967(6) 0.0372(16) Uani 1 1 d . . . . .
C5 C 0.2936(11) 0.8545(11) 0.5924(6) 0.0408(17) Uani 1 1 d . . . . .
H5 H 0.308416 0.971720 0.604070 0.049 Uiso 1 1 calc R U . . .
N5 N 0.2201(10) 1.1940(10) 0.4336(5) 0.0453(16) Uani 1 1 d . . . . .
C19 C 0.7578(9) 0.1180(9) 0.5839(6) 0.0318(15) Uani 1 1 d . . . . .
C24 C 0.8658(13) -0.5108(14) 0.8961(7) 0.075(2) Uani 1 1 d . . . . .
H24A H 0.970773 -0.474602 0.916136 0.089 Uiso 1 1 calc R U . . .
H24B H 0.851203 -0.639272 0.903593 0.089 Uiso 1 1 calc R U . . .
C10 C 0.0811(13) 1.1048(16) 0.0759(8) 0.082(3) Uani 1 1 d . . . . .
H10A H 0.197771 1.034940 0.055803 0.099 Uiso 1 1 calc R U . . .
H10B H -0.034339 1.078110 0.061653 0.099 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N7 N8 1.344(9) . ?
N7 C19 1.363(8) . ?
N2 C7 1.322(9) . ?
N2 N3 1.315(9) . ?
C7 C4 1.471(11) . ?
C7 N5 1.337(10) . ?
N3 N4 1.325(9) . ?
N3 C8 1.507(9) . ?
O6 H6 0.8400 . ?
O6 C21 1.413(9) . ?
O2 N1 1.235(8) . ?
O1 N1 1.235(9) . ?
N4 N5 1.299(9) . ?
O3 H3 0.8400 . ?
O3 C12 1.414(9) . ?
C2 H2 0.9500 . ?
C2 C1 1.396(10) . ?
C2 C3 1.363(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.409(10) . ?
C15 C14 1.397(11) . ?
O5 N6 1.215(10) . ?
C16 C17 1.378(10) . ?
C16 C19 1.463(9) . ?
C17 H17 0.9500 . ?
C17 C18 1.402(10) . ?
C1 N1 1.449(10) . ?
C1 C6 1.385(11) . ?
C20 C21 1.546(10) . ?
C20 C22 1.506(10) . ?
C20 C23 1.509(12) . ?
C20 N9 1.484(9) . ?
C14 H14 0.9500 . ?
C14 C13 1.389(11) . ?
N6 O4 1.218(9) . ?
N6 C13 1.481(10) . ?
N8 N9 1.311(9) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C24 1.333(12) . ?
N9 N10 1.346(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C8 1.534(11) . ?
N10 C19 1.340(9) . ?
C13 C18 1.360(10) . ?
C8 C9 1.516(11) . ?
C8 C11 1.510(12) . ?
C9 H9 0.9500 . ?
C9 C10 1.289(12) . ?
C3 H3A 0.9500 . ?
C3 C4 1.401(11) . ?
C6 H6A 0.9500 . ?
C6 C5 1.363(11) . ?
C18 H18 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C4 C5 1.385(10) . ?
C5 H5 0.9500 . ?
C24 H24A 0.9500 . ?
C24 H24B 0.9500 . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?

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
N8 N7 C19 107.6(6) . . ?
N3 N2 C7 101.2(6) . . ?
N2 C7 C4 123.7(7) . . ?
N2 C7 N5 113.4(7) . . ?
N5 C7 C4 122.9(7) . . ?
N2 N3 N4 113.1(6) . . ?
N2 N3 C8 123.2(6) . . ?
N4 N3 C8 123.6(6) . . ?
C21 O6 H6 109.5 . . ?
N5 N4 N3 107.1(6) . . ?
C12 O3 H3 109.5 . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C3 C2 C1 118.2(7) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.2(7) . . ?
C15 C16 C19 117.7(7) . . ?
C17 C16 C15 121.8(7) . . ?
C17 C16 C19 120.5(7) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.0(7) . . ?
C18 C17 H17 120.5 . . ?
C2 C1 N1 118.8(7) . . ?
C6 C1 C2 120.9(7) . . ?
C6 C1 N1 120.2(7) . . ?
C22 C20 C21 108.9(7) . . ?
C22 C20 C23 116.3(7) . . ?
C23 C20 C21 110.1(6) . . ?
N9 C20 C21 106.5(6) . . ?
N9 C20 C22 108.3(6) . . ?
N9 C20 C23 106.4(7) . . ?
C15 C14 H14 121.5 . . ?
C13 C14 C15 117.1(7) . . ?
C13 C14 H14 121.5 . . ?
O5 N6 O4 125.1(8) . . ?
O5 N6 C13 116.4(7) . . ?
O4 N6 C13 118.5(7) . . ?
O2 N1 C1 118.8(7) . . ?
O1 N1 O2 121.8(8) . . ?
O1 N1 C1 119.4(7) . . ?
N9 N8 N7 104.3(6) . . ?
O6 C21 C20 112.3(6) . . ?
O6 C21 H21A 109.1 . . ?
O6 C21 H21B 109.1 . . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.9 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23 118.1 . . ?
C24 C23 C20 123.8(9) . . ?
C24 C23 H23 118.1 . . ?
N8 N9 C20 122.4(7) . . ?
N8 N9 N10 115.5(6) . . ?
N10 N9 C20 121.9(6) . . ?
O3 C12 H12A 109.3 . . ?
O3 C12 H12B 109.3 . . ?
O3 C12 C8 111.7(7) . . ?
H12A C12 H12B 107.9 . . ?
C8 C12 H12A 109.3 . . ?
C8 C12 H12B 109.3 . . ?
C19 N10 N9 101.6(6) . . ?
C14 C13 N6 116.6(7) . . ?
C18 C13 C14 124.6(7) . . ?
C18 C13 N6 118.9(7) . . ?
N3 C8 C12 105.4(6) . . ?
N3 C8 C9 107.5(6) . . ?
N3 C8 C11 109.2(6) . . ?
C9 C8 C12 111.7(7) . . ?
C11 C8 C12 111.3(7) . . ?
C11 C8 C9 111.5(7) . . ?
C8 C9 H9 115.7 . . ?
C10 C9 C8 128.5(8) . . ?
C10 C9 H9 115.7 . . ?
C2 C3 H3A 118.9 . . ?
C2 C3 C4 122.3(7) . . ?
C4 C3 H3A 118.9 . . ?
C1 C6 H6A 120.3 . . ?
C5 C6 C1 119.4(7) . . ?
C5 C6 H6A 120.3 . . ?
C17 C18 H18 120.8 . . ?
C13 C18 C17 118.4(7) . . ?
C13 C18 H18 120.8 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C4 C7 122.5(7) . . ?
C5 C4 C7 119.9(7) . . ?
C5 C4 C3 117.5(8) . . ?
C6 C5 C4 121.7(7) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
N4 N5 C7 105.1(6) . . ?
N7 C19 C16 123.5(7) . . ?
N10 C19 N7 110.8(6) . . ?
N10 C19 C16 125.6(6) . . ?
C23 C24 H24A 120.0 . . ?
C23 C24 H24B 120.0 . . ?
H24A C24 H24B 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 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
N7 N8 N9 C20 176.6(6) . . . . ?
N7 N8 N9 N10 0.5(8) . . . . ?
N2 C7 C4 C3 -15.8(10) . . . . ?
N2 C7 C4 C5 164.3(7) . . . . ?
N2 C7 N5 N4 -0.9(9) . . . . ?
N2 N3 N4 N5 0.3(8) . . . . ?
N2 N3 C8 C12 -57.6(8) . . . . ?
N2 N3 C8 C9 61.6(9) . . . . ?
N2 N3 C8 C11 -177.3(7) . . . . ?
C7 N2 N3 N4 -0.8(7) . . . . ?
C7 N2 N3 C8 175.1(6) . . . . ?
C7 C4 C5 C6 -179.0(7) . . . . ?
N3 N2 C7 C4 -177.1(6) . . . . ?
N3 N2 C7 N5 1.1(8) . . . . ?
N3 N4 N5 C7 0.4(8) . . . . ?
N3 C8 C9 C10 -100.4(11) . . . . ?
N4 N3 C8 C12 117.9(7) . . . . ?
N4 N3 C8 C9 -122.9(7) . . . . ?
N4 N3 C8 C11 -1.8(9) . . . . ?
O3 C12 C8 N3 -56.1(8) . . . . ?
O3 C12 C8 C9 -172.5(6) . . . . ?
O3 C12 C8 C11 62.1(9) . . . . ?
C2 C1 N1 O2 174.6(7) . . . . ?
C2 C1 N1 O1 -6.6(10) . . . . ?
C2 C1 C6 C5 1.0(11) . . . . ?
C2 C3 C4 C7 179.8(6) . . . . ?
C2 C3 C4 C5 -0.3(11) . . . . ?
C15 C16 C17 C18 -0.7(10) . . . . ?
C15 C16 C19 N7 14.9(10) . . . . ?
C15 C16 C19 N10 -162.6(7) . . . . ?
C15 C14 C13 N6 -179.8(6) . . . . ?
C15 C14 C13 C18 0.4(11) . . . . ?
O5 N6 C13 C14 173.0(7) . . . . ?
O5 N6 C13 C18 -7.2(10) . . . . ?
C16 C15 C14 C13 -0.4(11) . . . . ?
C16 C17 C18 C13 0.7(10) . . . . ?
C17 C16 C19 N7 -166.4(7) . . . . ?
C17 C16 C19 N10 16.1(10) . . . . ?
C1 C2 C3 C4 -0.1(11) . . . . ?
C1 C6 C5 C4 -1.4(11) . . . . ?
C20 N9 N10 C19 -176.9(5) . . . . ?
C14 C15 C16 C17 0.5(11) . . . . ?
C14 C15 C16 C19 179.2(6) . . . . ?
C14 C13 C18 C17 -0.6(11) . . . . ?
N6 C13 C18 C17 179.6(6) . . . . ?
N1 C1 C6 C5 178.5(7) . . . . ?
N8 N7 C19 C16 -178.4(6) . . . . ?
N8 N7 C19 N10 -0.6(8) . . . . ?
N8 N9 N10 C19 -0.8(7) . . . . ?
C21 C20 C23 C24 -124.0(8) . . . . ?
C21 C20 N9 N8 -123.2(7) . . . . ?
C21 C20 N9 N10 52.6(8) . . . . ?
C22 C20 C21 O6 176.0(7) . . . . ?
C22 C20 C23 C24 0.4(12) . . . . ?
C22 C20 N9 N8 119.9(8) . . . . ?
C22 C20 N9 N10 -64.3(8) . . . . ?
C23 C20 C21 O6 -55.4(9) . . . . ?
C23 C20 N9 N8 -5.8(8) . . . . ?
C23 C20 N9 N10 170.1(6) . . . . ?
N9 C20 C21 O6 59.5(8) . . . . ?
N9 C20 C23 C24 121.0(8) . . . . ?
N9 N10 C19 N7 0.8(7) . . . . ?
N9 N10 C19 C16 178.6(6) . . . . ?
C12 C8 C9 C10 14.8(13) . . . . ?
O4 N6 C13 C14 -6.3(10) . . . . ?
O4 N6 C13 C18 173.5(7) . . . . ?
C8 N3 N4 N5 -175.6(6) . . . . ?
C3 C2 C1 N1 -177.7(6) . . . . ?
C3 C2 C1 C6 -0.3(10) . . . . ?
C3 C4 C5 C6 1.0(11) . . . . ?
C6 C1 N1 O2 -2.9(10) . . . . ?
C6 C1 N1 O1 175.9(7) . . . . ?
C11 C8 C9 C10 140.0(10) . . . . ?
C4 C7 N5 N4 177.2(6) . . . . ?
N5 C7 C4 C3 166.2(7) . . . . ?
N5 C7 C4 C5 -13.7(10) . . . . ?
C19 N7 N8 N9 0.0(8) . . . . ?
C19 C16 C17 C18 -179.3(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
