# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_m14243_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2nt6rg
_database_code_depnum_ccdc_archive 'CCDC 2467096'
loop_
_audit_author_name
_audit_author_address
'jingjing jiang'
;henan
China
;
_audit_update_record             
;
2025-06-25 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-06-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 N6 O'
_chemical_formula_sum            'C21 H22 N6 O'
_chemical_formula_weight         374.44
_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/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                   19.1428(19)
_cell_length_b                   10.6392(10)
_cell_length_c                   19.4801(19)
_cell_angle_alpha                90
_cell_angle_beta                 101.946(3)
_cell_angle_gamma                90
_cell_volume                     3881.5(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2334
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      19.980
_cell_measurement_theta_min      2.559
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.2586
_exptl_absorpt_correction_T_min  0.1729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1694 before and 0.0969 after correction.
The Ratio of minimum to maximum transmission is 0.6686.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2457
_diffrn_reflns_av_unetI/netI     0.1801
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            36233
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.945
_diffrn_reflns_theta_max         24.945
_diffrn_reflns_theta_min         2.137
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  'Helios multilayer optic'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_source            'Incoatc Ius 3.0 '
_diffrn_source_type              Microfocus
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2786
_reflns_number_total             6738
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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         0.378
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0098(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         6738
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2350
_refine_ls_R_factor_gt           0.1122
_refine_ls_restrained_S_all      1.028
_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)+(0.1153P)²+6.3278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2650
_refine_ls_wR_factor_ref         0.3328
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C19(H19A,H19B), C32(H32A,H32B), C41(H41A,
 H41B), C5(H5A,H5B), C25(H25A,H25B), C34(H34A,H34B), C39(H39A,H39B), C42(H42A,
 H42B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C20(H20), C23(H23), C31(H31), C35(H35), C36(H36), C38(H38),
 C40(H40), C2(H2), C3(H3), C17(H17), C21(H21), C27(H27), C28(H28), C29(H29),
 C30(H30), C33(H33)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C37(H37A,H37B,H37C)
;
_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 0.4146(3) 0.3148(5) 0.3556(2) 0.0622(14) Uani 1 1 d . . . . .
N1 N 0.3932(3) 0.5148(5) 0.3871(3) 0.0524(15) Uani 1 1 d . . . . .
N7 N 0.2254(3) 0.1164(6) 0.3872(3) 0.0668(18) Uani 1 1 d . . . . .
N8 N 0.2993(3) 0.1224(5) 0.3970(3) 0.0531(15) Uani 1 1 d . . . . .
N10 N 0.2001(3) 0.0423(6) 0.3345(3) 0.0672(18) Uani 1 1 d . . . . .
N11 N 0.2382(5) 0.4658(8) 0.4504(5) 0.097(3) Uani 1 1 d . . . . .
N12 N 0.2849(4) 0.4063(6) 0.4433(3) 0.0648(18) Uani 1 1 d . . . . .
C1 C 0.3212(4) 0.0486(6) 0.3463(3) 0.0452(16) Uani 1 1 d . . . . .
C7 C 0.3849(5) -0.0659(8) 0.2744(4) 0.070(2) Uani 1 1 d . . . . .
H7 H 0.427733 -0.088753 0.262413 0.085 Uiso 1 1 calc R U . . .
C8 C 0.2575(4) -0.0017(7) 0.3081(4) 0.0541(19) Uani 1 1 d . . . . .
C9 C 0.3635(4) 0.7838(8) 0.5390(4) 0.073(2) Uani 1 1 d . . . . .
H9 H 0.358549 0.844512 0.571996 0.087 Uiso 1 1 calc R U . . .
C10 C 0.3821(4) 0.6029(6) 0.4400(3) 0.0474(17) Uani 1 1 d . . . . .
C11 C 0.4535(4) 0.1997(8) 0.5515(4) 0.075(2) Uani 1 1 d . . . . .
H11A H 0.462868 0.288201 0.545389 0.090 Uiso 1 1 calc R U . . .
H11B H 0.499129 0.157445 0.565771 0.090 Uiso 1 1 calc R U . . .
C13 C 0.4141(4) 0.1453(7) 0.4820(4) 0.059(2) Uani 1 1 d . . . . .
H13A H 0.411495 0.054706 0.486438 0.071 Uiso 1 1 calc R U . . .
H13B H 0.441280 0.163133 0.446244 0.071 Uiso 1 1 calc R U . . .
C14 C 0.3385(4) 0.1970(7) 0.4577(3) 0.0512(18) Uani 1 1 d . . . . .
C15 C 0.4299(4) 0.5620(8) 0.3312(4) 0.067(2) Uani 1 1 d . . . . .
H15A H 0.424079 0.651469 0.326866 0.101 Uiso 1 1 calc R U . . .
H15B H 0.409360 0.522782 0.287316 0.101 Uiso 1 1 calc R U . . .
H15C H 0.479847 0.542055 0.343763 0.101 Uiso 1 1 calc R U . . .
C16 C 0.3394(4) 0.3368(7) 0.4367(3) 0.0509(18) Uani 1 1 d . . . . .
C18 C 0.3865(4) 0.3886(7) 0.3913(3) 0.0496(18) Uani 1 1 d . . . . .
C19 C 0.3359(5) 0.2386(9) 0.5870(4) 0.084(3) Uani 1 1 d . . . . .
H19A H 0.309049 0.221127 0.623026 0.100 Uiso 1 1 calc R U . . .
H19B H 0.338705 0.329129 0.582194 0.100 Uiso 1 1 calc R U . . .
C20 C 0.4056(4) 0.6768(8) 0.5588(4) 0.068(2) Uani 1 1 d . . . . .
H20 H 0.426905 0.664905 0.605792 0.082 Uiso 1 1 calc R U . . .
C23 C 0.3209(5) -0.1191(8) 0.2372(4) 0.076(2) Uani 1 1 d . . . . .
H23 H 0.322468 -0.173914 0.200372 0.091 Uiso 1 1 calc R U . . .
C31 C 0.3292(4) 0.7978(8) 0.4694(5) 0.073(2) Uani 1 1 d . . . . .
H31 H 0.299864 0.866878 0.455642 0.088 Uiso 1 1 calc R U . . .
C32 C 0.2971(4) 0.1830(7) 0.5182(4) 0.063(2) Uani 1 1 d . . . . .
H32A H 0.251017 0.223634 0.504334 0.076 Uiso 1 1 calc R U . . .
H32B H 0.288722 0.094398 0.525065 0.076 Uiso 1 1 calc R U . . .
C35 C 0.3862(4) 0.0187(8) 0.3281(4) 0.067(2) Uani 1 1 d . . . . .
H35 H 0.428784 0.054796 0.351408 0.080 Uiso 1 1 calc R U . . .
C36 C 0.3390(4) 0.7079(7) 0.4197(4) 0.062(2) Uani 1 1 d . . . . .
H36 H 0.316614 0.718092 0.372937 0.074 Uiso 1 1 calc R U . . .
C38 C 0.2560(5) -0.0922(8) 0.2537(4) 0.071(2) Uani 1 1 d . . . . .
H38 H 0.213842 -0.130452 0.230839 0.085 Uiso 1 1 calc R U . . .
C40 C 0.4158(4) 0.5885(7) 0.5094(4) 0.0569(19) Uani 1 1 d . . . . .
H40 H 0.445427 0.519720 0.523065 0.068 Uiso 1 1 calc R U . . .
C41 C 0.4108(5) 0.1851(10) 0.6093(4) 0.091(3) Uani 1 1 d . . . . .
H41A H 0.407748 0.096752 0.620492 0.110 Uiso 1 1 calc R U . . .
H41B H 0.435460 0.228119 0.651227 0.110 Uiso 1 1 calc R U . . .
O2 O 0.6412(3) 0.1910(5) 0.0886(3) 0.0663(15) Uani 1 1 d . . . . .
N2 N 0.5948(4) 0.4031(7) 0.2654(3) 0.0730(19) Uani 1 1 d . . . . .
N3 N 0.6129(3) -0.0067(6) 0.1203(3) 0.0576(16) Uani 1 1 d . . . . .
N4 N 0.5514(3) 0.1216(6) 0.2189(3) 0.0608(16) Uani 1 1 d . . . . .
N5 N 0.5457(4) 0.0725(7) 0.2698(4) 0.083(2) Uani 1 1 d . . . . .
N6 N 0.5878(3) 0.3979(5) 0.1944(3) 0.0544(16) Uani 1 1 d . . . . .
N9 N 0.6486(4) 0.4755(7) 0.2930(3) 0.080(2) Uani 1 1 d . . . . .
C2 C 0.7371(4) 0.6030(8) 0.2428(5) 0.075(2) Uani 1 1 d . . . . .
H2 H 0.761499 0.635599 0.285346 0.090 Uiso 1 1 calc R U . . .
C3 C 0.5762(4) -0.1876(7) 0.1808(4) 0.067(2) Uani 1 1 d . . . . .
H3 H 0.622036 -0.190978 0.208445 0.080 Uiso 1 1 calc R U . . .
C4 C 0.5568(3) 0.1795(6) 0.1611(3) 0.0473(17) Uani 1 1 d . . . . .
C5 C 0.3798(4) 0.3035(9) 0.0710(4) 0.081(3) Uani 1 1 d . . . . .
H5A H 0.340043 0.255018 0.045177 0.097 Uiso 1 1 calc R U . . .
H5B H 0.365553 0.391144 0.069740 0.097 Uiso 1 1 calc R U . . .
C6 C 0.6426(4) 0.4697(7) 0.1762(4) 0.0552(19) Uani 1 1 d . . . . .
C12 C 0.6063(4) 0.1228(7) 0.1192(4) 0.0539(19) Uani 1 1 d . . . . .
C17 C 0.7193(4) 0.5825(8) 0.1174(5) 0.075(2) Uani 1 1 d . . . . .
H17 H 0.733750 0.604342 0.076269 0.090 Uiso 1 1 calc R U . . .
C21 C 0.4394(4) -0.1806(8) 0.0989(4) 0.069(2) Uani 1 1 d . . . . .
H21 H 0.393452 -0.177108 0.071578 0.082 Uiso 1 1 calc R U . . .
C22 C 0.6796(4) 0.5205(7) 0.2394(4) 0.061(2) Uani 1 1 d . . . . .
C24 C 0.5581(4) -0.0939(6) 0.1314(4) 0.0508(18) Uani 1 1 d . . . . .
C25 C 0.4440(4) 0.2888(7) 0.0369(4) 0.068(2) Uani 1 1 d . . . . .
H25A H 0.432128 0.321642 -0.010527 0.082 Uiso 1 1 calc R U . . .
H25B H 0.454879 0.200120 0.034059 0.082 Uiso 1 1 calc R U . . .
C26 C 0.5297(4) 0.3158(7) 0.1547(3) 0.0551(19) Uani 1 1 d . . . . .
C27 C 0.6631(4) 0.5015(8) 0.1135(4) 0.066(2) Uani 1 1 d . . . . .
H27 H 0.639309 0.468859 0.070771 0.079 Uiso 1 1 calc R U . . .
C28 C 0.5244(5) -0.2790(8) 0.1892(4) 0.070(2) Uani 1 1 d . . . . .
H28 H 0.535654 -0.341937 0.222855 0.084 Uiso 1 1 calc R U . . .
C29 C 0.4570(5) -0.2728(9) 0.1465(5) 0.074(2) Uani 1 1 d . . . . .
H29 H 0.423213 -0.333503 0.150921 0.089 Uiso 1 1 calc R U . . .
C30 C 0.4900(4) -0.0894(7) 0.0899(4) 0.060(2) Uani 1 1 d . . . . .
H30 H 0.477788 -0.026649 0.056308 0.072 Uiso 1 1 calc R U . . .
C33 C 0.7559(4) 0.6337(9) 0.1812(6) 0.081(3) Uani 1 1 d . . . . .
H33 H 0.793400 0.689263 0.181364 0.097 Uiso 1 1 calc R U . . .
C34 C 0.5101(4) 0.3573(7) 0.0777(3) 0.061(2) Uani 1 1 d . . . . .
H34A H 0.501244 0.447074 0.075665 0.073 Uiso 1 1 calc R U . . .
H34B H 0.550170 0.340910 0.055511 0.073 Uiso 1 1 calc R U . . .
C37 C 0.6705(4) -0.0607(8) 0.0892(4) 0.077(2) Uani 1 1 d . . . . .
H37A H 0.655063 -0.064305 0.039098 0.116 Uiso 1 1 calc R U . . .
H37B H 0.681468 -0.143902 0.107255 0.116 Uiso 1 1 calc R U . . .
H37C H 0.712270 -0.008804 0.101060 0.116 Uiso 1 1 calc R U . . .
C39 C 0.3984(4) 0.2583(9) 0.1469(4) 0.072(2) Uani 1 1 d . . . . .
H39A H 0.357836 0.270929 0.168836 0.086 Uiso 1 1 calc R U . . .
H39B H 0.409165 0.169170 0.148003 0.086 Uiso 1 1 calc R U . . .
C42 C 0.4626(4) 0.3302(7) 0.1875(4) 0.060(2) Uani 1 1 d . . . . .
H42A H 0.473769 0.299951 0.235526 0.072 Uiso 1 1 calc R U . . .
H42B H 0.450423 0.418621 0.188661 0.072 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C18 1.243(8) . ?
N1 C10 1.442(8) . ?
N1 C15 1.499(8) . ?
N1 C18 1.352(9) . ?
N7 N8 1.389(8) . ?
N7 N10 1.306(8) . ?
N8 C1 1.391(8) . ?
N8 C14 1.492(8) . ?
N10 C8 1.386(9) . ?
N11 N12 1.126(9) . ?
N12 C16 1.307(10) . ?
C1 C8 1.397(9) . ?
C1 C35 1.401(9) . ?
C7 H7 0.9300 . ?
C7 C23 1.408(11) . ?
C7 C35 1.376(10) . ?
C8 C38 1.428(10) . ?
C9 H9 0.9300 . ?
C9 C20 1.402(11) . ?
C9 C31 1.386(10) . ?
C10 C36 1.396(10) . ?
C10 C40 1.381(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C13 1.523(9) . ?
C11 C41 1.530(12) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.529(9) . ?
C14 C16 1.544(10) . ?
C14 C32 1.556(9) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C18 1.493(10) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C32 1.511(10) . ?
C19 C41 1.520(12) . ?
C20 H20 0.9300 . ?
C20 C40 1.388(10) . ?
C23 H23 0.9300 . ?
C23 C38 1.376(11) . ?
C31 H31 0.9300 . ?
C31 C36 1.400(10) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C38 H38 0.9300 . ?
C40 H40 0.9300 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
O2 C12 1.222(8) . ?
N2 N6 1.362(7) . ?
N2 N9 1.309(8) . ?
N3 C12 1.384(9) . ?
N3 C24 1.449(9) . ?
N3 C37 1.479(9) . ?
N4 N5 1.144(8) . ?
N4 C4 1.308(9) . ?
N6 C6 1.403(9) . ?
N6 C26 1.496(9) . ?
N9 C22 1.389(9) . ?
C2 H2 0.9300 . ?
C2 C22 1.399(11) . ?
C2 C33 1.362(12) . ?
C3 H3 0.9300 . ?
C3 C24 1.379(9) . ?
C3 C28 1.423(11) . ?
C4 C12 1.499(9) . ?
C4 C26 1.537(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C25 1.521(10) . ?
C5 C39 1.525(11) . ?
C6 C22 1.396(9) . ?
C6 C27 1.398(10) . ?
C17 H17 0.9300 . ?
C17 C27 1.367(11) . ?
C17 C33 1.404(11) . ?
C21 H21 0.9300 . ?
C21 C29 1.345(11) . ?
C21 C30 1.406(10) . ?
C24 C30 1.386(9) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C34 1.532(10) . ?
C26 C34 1.533(9) . ?
C26 C42 1.558(10) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.385(10) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C33 H33 0.9300 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C42 1.523(10) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C15 117.5(5) . . ?
C18 N1 C10 124.9(6) . . ?
C18 N1 C15 116.2(6) . . ?
N10 N7 N8 109.6(6) . . ?
N7 N8 C1 108.9(5) . . ?
N7 N8 C14 117.6(5) . . ?
C1 N8 C14 133.4(6) . . ?
N7 N10 C8 107.6(6) . . ?
N11 N12 C16 178.7(9) . . ?
N8 C1 C8 103.7(6) . . ?
N8 C1 C35 136.2(7) . . ?
C8 C1 C35 120.1(6) . . ?
C23 C7 H7 119.0 . . ?
C35 C7 H7 119.0 . . ?
C35 C7 C23 122.1(8) . . ?
N10 C8 C1 110.1(6) . . ?
N10 C8 C38 127.3(7) . . ?
C1 C8 C38 122.4(7) . . ?
C20 C9 H9 120.5 . . ?
C31 C9 H9 120.5 . . ?
C31 C9 C20 119.1(8) . . ?
C36 C10 N1 118.9(6) . . ?
C40 C10 N1 121.3(6) . . ?
C40 C10 C36 119.7(6) . . ?
H11A C11 H11B 107.9 . . ?
C13 C11 H11A 109.2 . . ?
C13 C11 H11B 109.2 . . ?
C13 C11 C41 111.9(7) . . ?
C41 C11 H11A 109.2 . . ?
C41 C11 H11B 109.2 . . ?
C11 C13 H13A 108.8 . . ?
C11 C13 H13B 108.8 . . ?
C11 C13 C14 113.7(6) . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
N8 C14 C13 110.0(6) . . ?
N8 C14 C16 109.5(5) . . ?
N8 C14 C32 107.4(5) . . ?
C13 C14 C16 111.5(6) . . ?
C13 C14 C32 109.2(6) . . ?
C16 C14 C32 109.2(6) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N12 C16 C14 117.7(6) . . ?
N12 C16 C18 116.3(6) . . ?
C18 C16 C14 123.7(6) . . ?
O1 C18 N1 122.4(6) . . ?
O1 C18 C16 118.9(7) . . ?
N1 C18 C16 118.6(6) . . ?
H19A C19 H19B 108.0 . . ?
C32 C19 H19A 109.3 . . ?
C32 C19 H19B 109.3 . . ?
C32 C19 C41 111.5(7) . . ?
C41 C19 H19A 109.3 . . ?
C41 C19 H19B 109.3 . . ?
C9 C20 H20 119.5 . . ?
C40 C20 C9 120.9(7) . . ?
C40 C20 H20 119.5 . . ?
C7 C23 H23 119.0 . . ?
C38 C23 C7 121.9(7) . . ?
C38 C23 H23 119.0 . . ?
C9 C31 H31 120.1 . . ?
C9 C31 C36 119.9(8) . . ?
C36 C31 H31 120.1 . . ?
C14 C32 H32A 108.8 . . ?
C14 C32 H32B 108.8 . . ?
C19 C32 C14 113.6(6) . . ?
C19 C32 H32A 108.8 . . ?
C19 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?
C1 C35 H35 121.2 . . ?
C7 C35 C1 117.7(7) . . ?
C7 C35 H35 121.2 . . ?
C10 C36 C31 120.5(7) . . ?
C10 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
C8 C38 H38 122.2 . . ?
C23 C38 C8 115.6(7) . . ?
C23 C38 H38 122.2 . . ?
C10 C40 C20 119.9(7) . . ?
C10 C40 H40 120.0 . . ?
C20 C40 H40 120.0 . . ?
C11 C41 H41A 109.3 . . ?
C11 C41 H41B 109.3 . . ?
C19 C41 C11 111.6(7) . . ?
C19 C41 H41A 109.3 . . ?
C19 C41 H41B 109.3 . . ?
H41A C41 H41B 108.0 . . ?
N9 N2 N6 110.2(6) . . ?
C12 N3 C24 125.0(6) . . ?
C12 N3 C37 116.9(6) . . ?
C24 N3 C37 115.9(6) . . ?
N5 N4 C4 178.7(8) . . ?
N2 N6 C6 108.2(5) . . ?
N2 N6 C26 117.1(6) . . ?
C6 N6 C26 134.5(5) . . ?
N2 N9 C22 108.4(6) . . ?
C22 C2 H2 121.4 . . ?
C33 C2 H2 121.4 . . ?
C33 C2 C22 117.2(8) . . ?
C24 C3 H3 120.2 . . ?
C24 C3 C28 119.6(7) . . ?
C28 C3 H3 120.2 . . ?
N4 C4 C12 116.9(6) . . ?
N4 C4 C26 115.4(6) . . ?
C12 C4 C26 125.2(6) . . ?
H5A C5 H5B 108.2 . . ?
C25 C5 H5A 109.6 . . ?
C25 C5 H5B 109.6 . . ?
C25 C5 C39 110.1(6) . . ?
C39 C5 H5A 109.6 . . ?
C39 C5 H5B 109.6 . . ?
C22 C6 N6 104.9(6) . . ?
C22 C6 C27 119.6(7) . . ?
C27 C6 N6 135.4(7) . . ?
O2 C12 N3 122.8(6) . . ?
O2 C12 C4 119.9(7) . . ?
N3 C12 C4 117.3(7) . . ?
C27 C17 H17 118.8 . . ?
C27 C17 C33 122.4(8) . . ?
C33 C17 H17 118.8 . . ?
C29 C21 H21 119.7 . . ?
C29 C21 C30 120.6(8) . . ?
C30 C21 H21 119.7 . . ?
N9 C22 C2 129.4(8) . . ?
N9 C22 C6 108.2(7) . . ?
C6 C22 C2 122.4(8) . . ?
C3 C24 N3 118.8(7) . . ?
C3 C24 C30 120.2(7) . . ?
C30 C24 N3 120.9(6) . . ?
C5 C25 H25A 109.1 . . ?
C5 C25 H25B 109.1 . . ?
C5 C25 C34 112.3(6) . . ?
H25A C25 H25B 107.9 . . ?
C34 C25 H25A 109.1 . . ?
C34 C25 H25B 109.1 . . ?
N6 C26 C4 107.9(5) . . ?
N6 C26 C34 110.1(6) . . ?
N6 C26 C42 108.5(5) . . ?
C4 C26 C42 110.7(6) . . ?
C34 C26 C4 111.1(6) . . ?
C34 C26 C42 108.5(6) . . ?
C6 C27 H27 121.2 . . ?
C17 C27 C6 117.6(8) . . ?
C17 C27 H27 121.2 . . ?
C3 C28 H28 120.5 . . ?
C29 C28 C3 118.9(8) . . ?
C29 C28 H28 120.5 . . ?
C21 C29 C28 121.2(8) . . ?
C21 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C21 C30 H30 120.3 . . ?
C24 C30 C21 119.5(7) . . ?
C24 C30 H30 120.3 . . ?
C2 C33 C17 120.8(8) . . ?
C2 C33 H33 119.6 . . ?
C17 C33 H33 119.6 . . ?
C25 C34 C26 112.3(6) . . ?
C25 C34 H34A 109.2 . . ?
C25 C34 H34B 109.2 . . ?
C26 C34 H34A 109.2 . . ?
C26 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
N3 C37 H37A 109.5 . . ?
N3 C37 H37B 109.5 . . ?
N3 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C5 C39 H39A 109.6 . . ?
C5 C39 H39B 109.6 . . ?
H39A C39 H39B 108.1 . . ?
C42 C39 C5 110.3(7) . . ?
C42 C39 H39A 109.6 . . ?
C42 C39 H39B 109.6 . . ?
C26 C42 H42A 109.1 . . ?
C26 C42 H42B 109.1 . . ?
C39 C42 C26 112.5(6) . . ?
C39 C42 H42A 109.1 . . ?
C39 C42 H42B 109.1 . . ?
H42A C42 H42B 107.8 . . ?

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 C10 C36 C31 -177.5(6) . . . . ?
N1 C10 C40 C20 178.2(6) . . . . ?
N7 N8 C1 C8 -1.1(7) . . . . ?
N7 N8 C1 C35 178.7(8) . . . . ?
N7 N8 C14 C13 152.6(6) . . . . ?
N7 N8 C14 C16 -84.5(7) . . . . ?
N7 N8 C14 C32 33.9(8) . . . . ?
N7 N10 C8 C1 -0.4(8) . . . . ?
N7 N10 C8 C38 175.2(7) . . . . ?
N8 N7 N10 C8 -0.3(8) . . . . ?
N8 C1 C8 N10 1.0(8) . . . . ?
N8 C1 C8 C38 -174.9(7) . . . . ?
N8 C1 C35 C7 176.9(8) . . . . ?
N8 C14 C16 N12 86.1(7) . . . . ?
N8 C14 C16 C18 -75.8(8) . . . . ?
N8 C14 C32 C19 172.0(7) . . . . ?
N10 N7 N8 C1 1.0(7) . . . . ?
N10 N7 N8 C14 -176.5(6) . . . . ?
N10 C8 C38 C23 179.7(7) . . . . ?
N12 C16 C18 O1 -145.3(7) . . . . ?
N12 C16 C18 N1 30.3(9) . . . . ?
C1 N8 C14 C13 -24.1(10) . . . . ?
C1 N8 C14 C16 98.7(8) . . . . ?
C1 N8 C14 C32 -142.8(7) . . . . ?
C1 C8 C38 C23 -5.2(11) . . . . ?
C7 C23 C38 C8 3.5(12) . . . . ?
C8 C1 C35 C7 -3.4(11) . . . . ?
C9 C20 C40 C10 -2.6(12) . . . . ?
C9 C31 C36 C10 1.0(12) . . . . ?
C10 N1 C18 O1 -159.8(6) . . . . ?
C10 N1 C18 C16 24.8(10) . . . . ?
C11 C13 C14 N8 -169.5(6) . . . . ?
C11 C13 C14 C16 68.8(8) . . . . ?
C11 C13 C14 C32 -52.0(8) . . . . ?
C13 C11 C41 C19 -53.4(10) . . . . ?
C13 C14 C16 N12 -152.0(6) . . . . ?
C13 C14 C16 C18 46.1(9) . . . . ?
C13 C14 C32 C19 52.8(9) . . . . ?
C14 N8 C1 C8 175.8(7) . . . . ?
C14 N8 C1 C35 -4.4(13) . . . . ?
C14 C16 C18 O1 16.9(10) . . . . ?
C14 C16 C18 N1 -167.5(6) . . . . ?
C15 N1 C10 C36 62.5(8) . . . . ?
C15 N1 C10 C40 -114.3(8) . . . . ?
C15 N1 C18 O1 6.2(10) . . . . ?
C15 N1 C18 C16 -169.2(6) . . . . ?
C16 C14 C32 C19 -69.4(8) . . . . ?
C18 N1 C10 C36 -131.7(7) . . . . ?
C18 N1 C10 C40 51.5(10) . . . . ?
C20 C9 C31 C36 -2.1(12) . . . . ?
C23 C7 C35 C1 1.7(12) . . . . ?
C31 C9 C20 C40 2.9(12) . . . . ?
C32 C14 C16 N12 -31.2(8) . . . . ?
C32 C14 C16 C18 166.9(6) . . . . ?
C32 C19 C41 C11 54.0(10) . . . . ?
C35 C1 C8 N10 -178.9(6) . . . . ?
C35 C1 C8 C38 5.3(11) . . . . ?
C35 C7 C23 C38 -2.0(13) . . . . ?
C36 C10 C40 C20 1.4(11) . . . . ?
C40 C10 C36 C31 -0.7(11) . . . . ?
C41 C11 C13 C14 53.7(9) . . . . ?
C41 C19 C32 C14 -54.7(9) . . . . ?
N2 N6 C6 C22 -2.4(8) . . . . ?
N2 N6 C6 C27 -179.0(8) . . . . ?
N2 N6 C26 C4 -80.2(7) . . . . ?
N2 N6 C26 C34 158.4(6) . . . . ?
N2 N6 C26 C42 39.8(8) . . . . ?
N2 N9 C22 C2 178.3(8) . . . . ?
N2 N9 C22 C6 -1.2(9) . . . . ?
N3 C24 C30 C21 175.7(6) . . . . ?
N4 C4 C12 O2 -143.8(7) . . . . ?
N4 C4 C12 N3 32.9(9) . . . . ?
N4 C4 C26 N6 82.0(7) . . . . ?
N4 C4 C26 C34 -157.2(6) . . . . ?
N4 C4 C26 C42 -36.6(8) . . . . ?
N6 N2 N9 C22 -0.4(9) . . . . ?
N6 C6 C22 N9 2.2(8) . . . . ?
N6 C6 C22 C2 -177.3(7) . . . . ?
N6 C6 C27 C17 176.1(8) . . . . ?
N6 C26 C34 C25 -171.9(6) . . . . ?
N6 C26 C42 C39 175.3(6) . . . . ?
N9 N2 N6 C6 1.8(8) . . . . ?
N9 N2 N6 C26 178.3(6) . . . . ?
C3 C24 C30 C21 0.5(11) . . . . ?
C3 C28 C29 C21 -1.6(12) . . . . ?
C4 C26 C34 C25 68.6(8) . . . . ?
C4 C26 C42 C39 -66.5(8) . . . . ?
C5 C25 C34 C26 55.5(9) . . . . ?
C5 C39 C42 C26 -58.5(9) . . . . ?
C6 N6 C26 C4 95.2(8) . . . . ?
C6 N6 C26 C34 -26.2(10) . . . . ?
C6 N6 C26 C42 -144.9(7) . . . . ?
C12 N3 C24 C3 -130.2(8) . . . . ?
C12 N3 C24 C30 54.5(10) . . . . ?
C12 C4 C26 N6 -79.2(8) . . . . ?
C12 C4 C26 C34 41.6(9) . . . . ?
C12 C4 C26 C42 162.3(6) . . . . ?
C22 C2 C33 C17 -0.9(13) . . . . ?
C22 C6 C27 C17 -0.1(11) . . . . ?
C24 N3 C12 O2 -155.8(7) . . . . ?
C24 N3 C12 C4 27.6(10) . . . . ?
C24 C3 C28 C29 1.1(11) . . . . ?
C25 C5 C39 C42 57.2(9) . . . . ?
C26 N6 C6 C22 -178.1(7) . . . . ?
C26 N6 C6 C27 5.3(14) . . . . ?
C26 C4 C12 O2 17.1(10) . . . . ?
C26 C4 C12 N3 -166.1(6) . . . . ?
C27 C6 C22 N9 179.4(7) . . . . ?
C27 C6 C22 C2 -0.1(12) . . . . ?
C27 C17 C33 C2 0.9(13) . . . . ?
C28 C3 C24 N3 -175.8(6) . . . . ?
C28 C3 C24 C30 -0.5(11) . . . . ?
C29 C21 C30 C24 -1.0(11) . . . . ?
C30 C21 C29 C28 1.6(12) . . . . ?
C33 C2 C22 N9 -178.8(8) . . . . ?
C33 C2 C22 C6 0.6(12) . . . . ?
C33 C17 C27 C6 -0.3(12) . . . . ?
C34 C26 C42 C39 55.7(8) . . . . ?
C37 N3 C12 O2 6.8(11) . . . . ?
C37 N3 C12 C4 -169.9(6) . . . . ?
C37 N3 C24 C3 67.1(9) . . . . ?
C37 N3 C24 C30 -108.2(8) . . . . ?
C39 C5 C25 C34 -56.1(9) . . . . ?
C42 C26 C34 C25 -53.3(8) . . . . ?

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

data_m14231_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2401411'
loop_
_audit_author_name
_audit_author_address
'li pan'
;henu
China
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2026-01-06 downloaded from the CCDC.
;
_audit_creation_date             2024-06-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 N5 O2'
_chemical_formula_sum            'C17 H21 N5 O2'
_chemical_formula_weight         327.39
_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   19.850(2)
_cell_length_b                   9.741(2)
_cell_length_c                   19.851(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.070(7)
_cell_angle_gamma                90
_cell_volume                     3557.1(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2203
_cell_measurement_temperature    296.30
_cell_measurement_theta_max      21.375
_cell_measurement_theta_min      2.474
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.2586
_exptl_absorpt_correction_T_min  0.1913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1037 before and 0.0640 after correction.
The Ratio of minimum to maximum transmission is 0.7398.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1251
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15296
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.053
_diffrn_reflns_theta_max         25.053
_diffrn_reflns_theta_min         2.214
_diffrn_ambient_temperature      296.30
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  'Helios multilayer optic'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_source            'Incoatc Ius 3.0 '
_diffrn_source_type              Microfocus
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1495
_reflns_number_total             3136
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0050(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1531
_refine_ls_R_factor_gt           0.0675
_refine_ls_restrained_S_all      1.030
_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)+(0.0960P)²+0.4586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.2181
_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. Restrained distances
 C16-C17
 1.53 with sigma of 0.01
3. Rigid bond restraints
 N1, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N4, C14
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C16(H16A,H16B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
5.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 0.34956(14) 0.7026(3) -0.15635(13) 0.0831(9) Uani 1 1 d . . . . .
O2 O 0.42264(15) 0.5331(3) -0.08850(14) 0.0923(10) Uani 1 1 d . . . . .
N1 N 0.28079(17) 0.5478(5) 0.10245(18) 0.0953(12) Uani 1 1 d . U . . .
N2 N 0.31976(18) 0.6446(4) 0.08762(17) 0.0851(10) Uani 1 1 d . . . . .
N3 N 0.37140(14) 0.5801(3) 0.06912(15) 0.0627(8) Uani 1 1 d . . . . .
N4 N 0.33896(17) 0.8132(3) -0.04390(15) 0.0690(9) Uani 1 1 d . U . . .
N5 N 0.3016(2) 0.9050(4) -0.05318(19) 0.0978(12) Uani 1 1 d . . . . .
C1 C 0.3061(2) 0.4212(5) 0.0924(2) 0.0799(12) Uani 1 1 d . U . . .
C2 C 0.2833(3) 0.2867(7) 0.1009(2) 0.1054(17) Uani 1 1 d . U . . .
H2 H 0.245035 0.271373 0.116238 0.126 Uiso 1 1 calc R U . . .
C3 C 0.3202(3) 0.1804(7) 0.0854(3) 0.118(2) Uani 1 1 d . . . . .
H3 H 0.306139 0.090927 0.090005 0.142 Uiso 1 1 calc R U . . .
C4 C 0.3777(3) 0.2013(4) 0.0632(2) 0.1004(15) Uani 1 1 d . . . . .
H4 H 0.401177 0.125702 0.053399 0.120 Uiso 1 1 calc R U . . .
C5 C 0.4007(2) 0.3299(4) 0.0554(2) 0.0763(11) Uani 1 1 d . . . . .
H5 H 0.439257 0.343534 0.040366 0.092 Uiso 1 1 calc R U . . .
C6 C 0.36430(18) 0.4403(4) 0.07091(18) 0.0616(9) Uani 1 1 d . . . . .
C7 C 0.42149(18) 0.6611(3) 0.04533(18) 0.0580(9) Uani 1 1 d . . . . .
H7 H 0.459750 0.597666 0.045180 0.070 Uiso 1 1 calc R U . . .
C8 C 0.45976(18) 0.7750(3) 0.10034(17) 0.0628(10) Uani 1 1 d . . . . .
H8 H 0.423378 0.843717 0.099390 0.075 Uiso 1 1 calc R U . . .
C9 C 0.4949(2) 0.7205(4) 0.17728(18) 0.0764(11) Uani 1 1 d . . . . .
H9A H 0.528368 0.647381 0.178220 0.092 Uiso 1 1 calc R U . . .
H9B H 0.457585 0.682103 0.192232 0.092 Uiso 1 1 calc R U . . .
C10 C 0.5357(2) 0.8316(5) 0.2308(2) 0.0983(14) Uani 1 1 d . . . . .
H10A H 0.501331 0.899868 0.233847 0.118 Uiso 1 1 calc R U . . .
H10B H 0.559168 0.791246 0.278621 0.118 Uiso 1 1 calc R U . . .
C11 C 0.5921(2) 0.9006(5) 0.2087(2) 0.1030(15) Uani 1 1 d . . . . .
H11A H 0.629733 0.834919 0.211337 0.124 Uiso 1 1 calc R U . . .
H11B H 0.614462 0.974860 0.242153 0.124 Uiso 1 1 calc R U . . .
C12 C 0.5588(3) 0.9568(5) 0.1324(2) 0.1060(16) Uani 1 1 d . . . . .
H12A H 0.596855 0.993599 0.118130 0.127 Uiso 1 1 calc R U . . .
H12B H 0.525820 1.031024 0.131227 0.127 Uiso 1 1 calc R U . . .
C13 C 0.5174(2) 0.8449(4) 0.0787(2) 0.0836(12) Uani 1 1 d . . . . .
H13A H 0.494147 0.885306 0.030822 0.100 Uiso 1 1 calc R U . . .
H13B H 0.551617 0.776361 0.075714 0.100 Uiso 1 1 calc R U . . .
C14 C 0.38402(18) 0.7082(3) -0.03149(18) 0.0586(9) Uani 1 1 d . U . . .
C15 C 0.3874(2) 0.6376(4) -0.0932(2) 0.0685(10) Uani 1 1 d . . . . .
C16 C 0.3511(3) 0.6421(6) -0.2230(3) 0.1220(18) Uani 1 1 d D . . . .
H16A H 0.341131 0.712406 -0.260093 0.146 Uiso 1 1 calc R U . . .
H16B H 0.399099 0.605022 -0.213880 0.146 Uiso 1 1 calc R U . . .
C17 C 0.2973(4) 0.5332(7) -0.2487(3) 0.166(3) Uani 1 1 d D . . . .
H17A H 0.293957 0.503600 -0.296010 0.250 Uiso 1 1 calc R U . . .
H17B H 0.250818 0.566982 -0.251629 0.250 Uiso 1 1 calc R U . . .
H17C H 0.311469 0.457209 -0.215573 0.250 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.353(4) . ?
O1 C16 1.460(5) . ?
O2 C15 1.219(4) . ?
N1 N2 1.321(5) . ?
N1 C1 1.374(5) . ?
N2 N3 1.365(4) . ?
N3 C6 1.371(4) . ?
N3 C7 1.479(4) . ?
N4 N5 1.132(4) . ?
N4 C14 1.319(4) . ?
C1 C2 1.416(6) . ?
C1 C6 1.387(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(5) . ?
C7 H7 0.9800 . ?
C7 C8 1.541(4) . ?
C7 C14 1.496(5) . ?
C8 H8 0.9800 . ?
C8 C9 1.517(5) . ?
C8 C13 1.525(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.520(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.506(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.508(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.531(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.428(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.455(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C15 O1 C16 117.2(3) . . ?
N2 N1 C1 109.4(3) . . ?
N1 N2 N3 107.1(3) . . ?
N2 N3 C6 110.8(3) . . ?
N2 N3 C7 120.2(3) . . ?
C6 N3 C7 128.8(3) . . ?
N5 N4 C14 178.2(4) . . ?
N1 C1 C2 131.5(5) . . ?
N1 C1 C6 108.4(4) . . ?
C6 C1 C2 120.1(5) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 C1 116.8(5) . . ?
C3 C2 H2 121.6 . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.4(5) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.5(5) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 121.3 . . ?
C4 C5 C6 117.5(4) . . ?
C6 C5 H5 121.3 . . ?
N3 C6 C1 104.3(4) . . ?
N3 C6 C5 134.0(3) . . ?
C1 C6 C5 121.7(4) . . ?
N3 C7 H7 106.2 . . ?
N3 C7 C8 111.7(3) . . ?
N3 C7 C14 110.7(3) . . ?
C8 C7 H7 106.2 . . ?
C14 C7 H7 106.2 . . ?
C14 C7 C8 115.2(3) . . ?
C7 C8 H8 108.3 . . ?
C9 C8 C7 112.3(3) . . ?
C9 C8 H8 108.3 . . ?
C9 C8 C13 109.3(3) . . ?
C13 C8 C7 110.1(3) . . ?
C13 C8 H8 108.3 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C8 C9 C10 112.2(3) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C9 111.9(4) . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C10 C11 C12 111.2(4) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C11 C12 C13 111.0(4) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C8 C13 C12 112.6(3) . . ?
C8 C13 H13A 109.1 . . ?
C8 C13 H13B 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
N4 C14 C7 118.1(3) . . ?
N4 C14 C15 117.4(3) . . ?
C15 C14 C7 124.1(3) . . ?
O1 C15 C14 112.4(3) . . ?
O2 C15 O1 124.4(3) . . ?
O2 C15 C14 123.2(4) . . ?
O1 C16 H16A 109.6 . . ?
O1 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 O1 110.5(4) . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 N3 C6 1.1(4) . . . . ?
N1 N2 N3 C7 176.5(3) . . . . ?
N1 C1 C2 C3 179.3(4) . . . . ?
N1 C1 C6 N3 0.1(4) . . . . ?
N1 C1 C6 C5 -179.0(3) . . . . ?
N2 N1 C1 C2 -180.0(4) . . . . ?
N2 N1 C1 C6 0.6(4) . . . . ?
N2 N3 C6 C1 -0.7(3) . . . . ?
N2 N3 C6 C5 178.1(4) . . . . ?
N2 N3 C7 C8 52.6(4) . . . . ?
N2 N3 C7 C14 -77.1(4) . . . . ?
N3 C7 C8 C9 51.2(4) . . . . ?
N3 C7 C8 C13 173.3(3) . . . . ?
N3 C7 C14 N4 77.2(4) . . . . ?
N3 C7 C14 C15 -95.4(4) . . . . ?
N4 C14 C15 O1 8.2(5) . . . . ?
N4 C14 C15 O2 -174.1(4) . . . . ?
C1 N1 N2 N3 -1.1(4) . . . . ?
C1 C2 C3 C4 0.7(7) . . . . ?
C2 C1 C6 N3 -179.4(3) . . . . ?
C2 C1 C6 C5 1.6(5) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C4 C5 C6 N3 -179.7(4) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C6 N3 C7 C8 -132.9(3) . . . . ?
C6 N3 C7 C14 97.4(4) . . . . ?
C6 C1 C2 C3 -1.4(6) . . . . ?
C7 N3 C6 C1 -175.6(3) . . . . ?
C7 N3 C6 C5 3.2(6) . . . . ?
C7 C8 C9 C10 177.2(3) . . . . ?
C7 C8 C13 C12 -178.5(3) . . . . ?
C7 C14 C15 O1 -179.2(3) . . . . ?
C7 C14 C15 O2 -1.5(6) . . . . ?
C8 C7 C14 N4 -50.6(4) . . . . ?
C8 C7 C14 C15 136.8(3) . . . . ?
C8 C9 C10 C11 -56.0(5) . . . . ?
C9 C8 C13 C12 -54.7(4) . . . . ?
C9 C10 C11 C12 55.1(5) . . . . ?
C10 C11 C12 C13 -54.3(5) . . . . ?
C11 C12 C13 C8 55.2(5) . . . . ?
C13 C8 C9 C10 54.7(4) . . . . ?
C14 C7 C8 C9 178.5(3) . . . . ?
C14 C7 C8 C13 -59.4(4) . . . . ?
C15 O1 C16 C17 83.3(5) . . . . ?
C16 O1 C15 O2 0.4(6) . . . . ?
C16 O1 C15 C14 178.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
