# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_obora-yamaguchi221108a
_database_code_depnum_ccdc_archive 'CCDC 2498999'
loop_
_audit_author_name
_audit_author_address
'Tetsuaki Fujihara'
;Kyoto University
Japan
;
_audit_update_record             
;
2025-10-30 deposited with the CCDC.	2025-12-17 downloaded from the CCDC.
;
_audit_creation_date             2022-11-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H18 N2 O3)'
_chemical_formula_sum            'C28 H36 N4 O6'
_chemical_formula_weight         524.61
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0284(14)
_cell_length_b                   11.127(2)
_cell_length_c                   16.994(4)
_cell_angle_alpha                88.080(6)
_cell_angle_beta                 84.490(6)
_cell_angle_gamma                90.002(7)
_cell_volume                     1322.2(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2638
_cell_measurement_temperature    153
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             560
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10696
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.469
_diffrn_reflns_theta_min         3.042
_diffrn_ambient_temperature      153.00
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9794
	          2theta: -20.0418
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 4.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9794
	          2theta: -20.0418
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3358
_reflns_number_total             5759
_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       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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         0.245
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.895
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5759
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      0.895
_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)+(0.0373P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0841
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H6A,H6B} of C6, {H8A,H8B} of C8, {H20A,H20B} of C20, {H7A,
  H7B} of C7, {H22A,H22B} of C22, {H21A,H21B} of C21
 At 1.5 times of:
  All C(H,H,H) groups, {H4A,H4B} of C4
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B), C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C26(H26), C27(H27), C24(H24), C10(H10), C11(H11), C25(H25)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.37863(13) 0.38281(8) 0.88739(5) 0.0274(2) Uani 1 1 d . . . . .
O6 O 0.89725(14) 0.84544(9) 0.34300(6) 0.0341(3) Uani 1 1 d . . . . .
O3 O 0.44311(14) 0.76823(8) 0.40468(6) 0.0324(3) Uani 1 1 d . . . . .
O4 O 0.90143(13) 0.81247(9) 0.87842(5) 0.0283(2) Uani 1 1 d . . . . .
O2 O 0.26333(14) 0.62072(9) 0.37603(6) 0.0351(3) Uani 1 1 d . . . . .
O5 O 0.73460(14) 1.00964(9) 0.36400(6) 0.0351(3) Uani 1 1 d . . . . .
N2 N 0.34941(15) 0.67562(10) 0.42360(7) 0.0254(3) Uani 1 1 d . . . . .
N3 N 0.83449(15) 0.83839(9) 0.71620(6) 0.0222(3) Uani 1 1 d . . . . .
N1 N 0.31648(15) 0.49586(9) 0.73844(6) 0.0221(3) Uani 1 1 d . . . . .
N4 N 0.81634(16) 0.91902(11) 0.38794(7) 0.0264(3) Uani 1 1 d . . . . .
C13 C 0.42884(17) 0.69299(12) 0.56002(8) 0.0224(3) Uani 1 1 d . . . . .
H13 H 0.494128 0.766146 0.544909 0.027 Uiso 1 1 calc R U . . .
C28 C 0.82081(17) 0.89806(12) 0.47247(7) 0.0201(3) Uani 1 1 d . . . . .
C12 C 0.24378(18) 0.52404(12) 0.52620(8) 0.0224(3) Uani 1 1 d . . . . .
H12 H 0.183525 0.481402 0.487864 0.027 Uiso 1 1 calc R U . . .
C26 C 0.73544(17) 0.97997(12) 0.52432(8) 0.0217(3) Uani 1 1 d . . . . .
H26 H 0.672878 1.048834 0.504727 0.026 Uiso 1 1 calc R U . . .
C14 C 0.34025(17) 0.63054(12) 0.50485(8) 0.0201(3) Uani 1 1 d . . . . .
C27 C 0.91364(17) 0.79846(12) 0.50003(8) 0.0214(3) Uani 1 1 d . . . . .
H27 H 0.972592 0.743315 0.463865 0.026 Uiso 1 1 calc R U . . .
C23 C 0.83438(17) 0.85957(12) 0.63516(7) 0.0191(3) Uani 1 1 d . . . . .
C24 C 0.74198(18) 0.96076(12) 0.60456(8) 0.0219(3) Uani 1 1 d . . . . .
H24 H 0.682940 1.016930 0.639985 0.026 Uiso 1 1 calc R U . . .
C5 C 0.25636(18) 0.32406(12) 0.83655(8) 0.0222(3) Uani 1 1 d . . . . .
C10 C 0.23561(18) 0.48037(12) 0.60301(8) 0.0225(3) Uani 1 1 d . . . . .
H10 H 0.167377 0.408014 0.617437 0.027 Uiso 1 1 calc R U . . .
C11 C 0.42250(18) 0.64915(11) 0.63701(8) 0.0222(3) Uani 1 1 d . . . . .
H11 H 0.483849 0.692662 0.674622 0.027 Uiso 1 1 calc R U . . .
C25 C 0.92078(17) 0.77899(12) 0.58027(8) 0.0219(3) Uani 1 1 d . . . . .
H25 H 0.985009 0.710122 0.598901 0.026 Uiso 1 1 calc R U . . .
C9 C 0.32637(17) 0.54062(11) 0.66099(8) 0.0199(3) Uani 1 1 d . . . . .
C19 C 0.77878(18) 0.90858(12) 0.85409(8) 0.0234(3) Uani 1 1 d . . . . .
C20 C 0.8385(2) 0.94159(13) 0.76766(8) 0.0253(3) Uani 1 1 d . . . . .
H20A H 0.7557(19) 1.0044(12) 0.7493(8) 0.030 Uiso 1 1 d . U . . .
H20B H 0.968(2) 0.9756(12) 0.7629(8) 0.030 Uiso 1 1 d . U . . .
C6 C 0.31690(19) 0.36428(11) 0.75122(8) 0.0229(3) Uani 1 1 d . . . . .
H6A H 0.447042 0.333742 0.735898 0.028 Uiso 1 1 calc R U . . .
H6B H 0.229217 0.328032 0.716332 0.028 Uiso 1 1 calc R U . . .
C17 C 0.56904(19) 0.87151(12) 0.87150(8) 0.0238(3) Uani 1 1 d . . . . .
C8 C 0.43247(19) 0.55322(12) 0.79331(8) 0.0262(3) Uani 1 1 d . . . . .
H8A H 0.417499 0.641573 0.788712 0.031 Uiso 1 1 calc R U . . .
H8B H 0.568891 0.534057 0.779495 0.031 Uiso 1 1 calc R U . . .
C7 C 0.3730(2) 0.51034(12) 0.87732(8) 0.0285(3) Uani 1 1 d . . . . .
H7A H 0.458869 0.546641 0.912943 0.034 Uiso 1 1 calc R U . . .
H7B H 0.241554 0.538451 0.892874 0.034 Uiso 1 1 calc R U . . .
C18 C 0.8240(3) 1.01378(15) 0.90416(9) 0.0342(4) Uani 1 1 d . . . . .
H18A H 0.792(2) 0.9937(14) 0.9629(9) 0.051 Uiso 1 1 d . U . . .
H18B H 0.752(2) 1.0830(14) 0.8918(9) 0.051 Uiso 1 1 d . U . . .
H18C H 0.966(2) 1.0299(13) 0.8964(9) 0.051 Uiso 1 1 d . U . . .
C21 C 0.8878(2) 0.71028(13) 0.83156(8) 0.0281(3) Uani 1 1 d . . . . .
H21A H 0.754488 0.680181 0.837917 0.034 Uiso 1 1 calc R U . . .
H21B H 0.970752 0.645851 0.850680 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3008(2) 0.19086(14) 0.84496(10) 0.0310(4) Uani 1 1 d . . . . .
H4A H 0.232(2) 0.1466(13) 0.8065(9) 0.046 Uiso 1 1 d . U . . .
H4B H 0.264(2) 0.1604(13) 0.8998(10) 0.046 Uiso 1 1 d . U . . .
C22 C 0.94624(19) 0.73781(13) 0.74451(8) 0.0272(3) Uani 1 1 d . . . . .
H22A H 1.083992 0.758296 0.736845 0.033 Uiso 1 1 calc R U . . .
H22B H 0.925087 0.665938 0.713638 0.033 Uiso 1 1 calc R U . . .
C16 C 0.5141(3) 0.81654(17) 0.95208(10) 0.0367(4) Uani 1 1 d . . . . .
C3 C 0.04623(19) 0.34649(12) 0.86335(8) 0.0257(3) Uani 1 1 d . . . . .
C1 C -0.0884(3) 0.35388(18) 0.80960(12) 0.0491(5) Uani 1 1 d . . . . .
C2 C -0.0074(3) 0.3467(2) 0.94650(12) 0.0548(6) Uani 1 1 d . . . . .
C15 C 0.4391(2) 0.89128(14) 0.82082(10) 0.0315(4) Uani 1 1 d . . . . .
H4C H 0.433(2) 0.1791(13) 0.8344(8) 0.038(4) Uiso 1 1 d . . . . .
H15A H 0.472(2) 0.9276(13) 0.7692(9) 0.040(5) Uiso 1 1 d . . . . .
H15B H 0.306(2) 0.8733(12) 0.8370(8) 0.039(4) Uiso 1 1 d . . . . .
H16A H 0.598(2) 0.7461(14) 0.9638(9) 0.047(5) Uiso 1 1 d . . . . .
H16B H 0.538(2) 0.8786(16) 0.9929(10) 0.059(5) Uiso 1 1 d . . . . .
H16C H 0.380(2) 0.7927(13) 0.9578(9) 0.046(5) Uiso 1 1 d . . . . .
H1A H -0.219(2) 0.3607(13) 0.8284(9) 0.047(5) Uiso 1 1 d . . . . .
H2A H 0.066(2) 0.3918(17) 0.9783(10) 0.064(6) Uiso 1 1 d . . . . .
H2B H -0.144(2) 0.3629(14) 0.9593(9) 0.054(5) Uiso 1 1 d . . . . .
H1B H -0.065(2) 0.3765(15) 0.7618(10) 0.056(6) Uiso 1 1 d . . . . .
H2C H 0.033(6) 0.257(4) 0.972(2) 0.26(2) Uiso 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
O1 C5 1.4467(15) . ?
O1 C7 1.4247(16) . ?
O6 N4 1.2392(14) . ?
O3 N2 1.2393(14) . ?
O4 C19 1.4480(16) . ?
O4 C21 1.4183(16) . ?
O2 N2 1.2327(13) . ?
O5 N4 1.2368(14) . ?
N2 C14 1.4489(16) . ?
N3 C23 1.3895(16) . ?
N3 C20 1.4685(17) . ?
N3 C22 1.4620(16) . ?
N1 C9 1.3870(16) . ?
N1 C6 1.4730(16) . ?
N1 C8 1.4585(16) . ?
N4 C28 1.4509(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.3803(18) . ?
C13 C11 1.3777(18) . ?
C28 C26 1.3855(17) . ?
C28 C27 1.3774(18) . ?
C12 H12 0.9500 . ?
C12 C14 1.3855(18) . ?
C12 C10 1.3736(18) . ?
C26 H26 0.9500 . ?
C26 C24 1.3783(17) . ?
C27 H27 0.9500 . ?
C27 C25 1.3792(17) . ?
C23 C24 1.4091(18) . ?
C23 C25 1.4107(17) . ?
C24 H24 0.9500 . ?
C5 C6 1.5238(17) . ?
C5 C4 1.5196(19) . ?
C5 C3 1.5262(19) . ?
C10 H10 0.9500 . ?
C10 C9 1.4114(17) . ?
C11 H11 0.9500 . ?
C11 C9 1.4125(17) . ?
C25 H25 0.9500 . ?
C19 C20 1.5211(18) . ?
C19 C17 1.5293(19) . ?
C19 C18 1.521(2) . ?
C20 H20A 0.972(14) . ?
C20 H20B 0.984(14) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C17 C16 1.497(2) . ?
C17 C15 1.3279(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.5102(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C18 H18A 1.019(16) . ?
C18 H18B 0.948(16) . ?
C18 H18C 1.009(16) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.5178(17) . ?
C4 H4A 0.994(15) . ?
C4 H4B 0.991(16) . ?
C4 H4C 0.939(15) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C16 H16A 1.006(16) . ?
C16 H16B 1.020(17) . ?
C16 H16C 0.976(16) . ?
C3 C1 1.377(2) . ?
C3 C2 1.427(2) . ?
C1 H1A 0.947(16) . ?
C1 H1B 0.843(17) . ?
C2 H2A 0.939(18) . ?
C2 H2B 0.984(17) . ?
C2 H2C 1.12(4) . ?
C15 H15A 0.961(15) . ?
C15 H15B 0.968(15) . ?

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
C7 O1 C5 111.81(10) . . ?
C21 O4 C19 111.34(10) . . ?
O3 N2 C14 118.64(11) . . ?
O2 N2 O3 122.55(12) . . ?
O2 N2 C14 118.81(11) . . ?
C23 N3 C20 118.82(11) . . ?
C23 N3 C22 118.70(11) . . ?
C22 N3 C20 111.58(11) . . ?
C9 N1 C6 117.57(10) . . ?
C9 N1 C8 118.40(10) . . ?
C8 N1 C6 110.53(10) . . ?
O6 N4 C28 118.06(12) . . ?
O5 N4 O6 123.07(12) . . ?
O5 N4 C28 118.87(12) . . ?
C14 C13 H13 120.0 . . ?
C11 C13 H13 120.0 . . ?
C11 C13 C14 119.95(12) . . ?
C26 C28 N4 119.55(12) . . ?
C27 C28 N4 119.57(12) . . ?
C27 C28 C26 120.86(12) . . ?
C14 C12 H12 120.1 . . ?
C10 C12 H12 120.1 . . ?
C10 C12 C14 119.72(12) . . ?
C28 C26 H26 120.3 . . ?
C24 C26 C28 119.49(13) . . ?
C24 C26 H26 120.3 . . ?
C13 C14 N2 119.98(12) . . ?
C13 C14 C12 120.61(12) . . ?
C12 C14 N2 119.41(12) . . ?
C28 C27 H27 120.1 . . ?
C28 C27 C25 119.84(12) . . ?
C25 C27 H27 120.1 . . ?
N3 C23 C24 121.12(12) . . ?
N3 C23 C25 121.58(12) . . ?
C24 C23 C25 117.26(12) . . ?
C26 C24 C23 121.39(12) . . ?
C26 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
O1 C5 C6 108.46(10) . . ?
O1 C5 C4 105.27(11) . . ?
O1 C5 C3 110.69(10) . . ?
C6 C5 C3 114.33(11) . . ?
C4 C5 C6 107.63(12) . . ?
C4 C5 C3 110.02(11) . . ?
C12 C10 H10 119.3 . . ?
C12 C10 C9 121.46(12) . . ?
C9 C10 H10 119.3 . . ?
C13 C11 H11 119.4 . . ?
C13 C11 C9 121.13(12) . . ?
C9 C11 H11 119.4 . . ?
C27 C25 C23 121.15(13) . . ?
C27 C25 H25 119.4 . . ?
C23 C25 H25 119.4 . . ?
N1 C9 C10 120.91(11) . . ?
N1 C9 C11 121.95(12) . . ?
C10 C9 C11 117.12(12) . . ?
O4 C19 C20 108.14(11) . . ?
O4 C19 C17 110.01(11) . . ?
O4 C19 C18 104.66(11) . . ?
C20 C19 C17 114.39(12) . . ?
C20 C19 C18 108.76(12) . . ?
C18 C19 C17 110.40(12) . . ?
N3 C20 C19 112.80(12) . . ?
N3 C20 H20A 109.3(8) . . ?
N3 C20 H20B 109.1(8) . . ?
C19 C20 H20A 109.9(8) . . ?
C19 C20 H20B 109.1(8) . . ?
H20A C20 H20B 106.4(11) . . ?
N1 C6 C5 113.25(11) . . ?
N1 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C16 C17 C19 115.82(13) . . ?
C15 C17 C19 123.17(14) . . ?
C15 C17 C16 120.93(14) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 C7 110.64(11) . . ?
H8A C8 H8B 108.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
O1 C7 C8 112.77(11) . . ?
O1 C7 H7A 109.0 . . ?
O1 C7 H7B 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C19 C18 H18A 111.3(8) . . ?
C19 C18 H18B 111.5(10) . . ?
C19 C18 H18C 108.7(9) . . ?
H18A C18 H18B 107.2(13) . . ?
H18A C18 H18C 106.3(12) . . ?
H18B C18 H18C 111.7(13) . . ?
O4 C21 H21A 109.1 . . ?
O4 C21 H21B 109.1 . . ?
O4 C21 C22 112.41(11) . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C5 C4 H4A 108.9(9) . . ?
C5 C4 H4B 110.6(9) . . ?
C5 C4 H4C 109.4(9) . . ?
H4A C4 H4B 110.8(12) . . ?
H4A C4 H4C 109.7(12) . . ?
H4B C4 H4C 107.5(12) . . ?
N3 C22 C21 110.15(11) . . ?
N3 C22 H22A 109.6 . . ?
N3 C22 H22B 109.6 . . ?
C21 C22 H22A 109.6 . . ?
C21 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C17 C16 H16A 111.6(9) . . ?
C17 C16 H16B 108.1(9) . . ?
C17 C16 H16C 110.8(9) . . ?
H16A C16 H16B 105.5(13) . . ?
H16A C16 H16C 110.5(12) . . ?
H16B C16 H16C 110.1(13) . . ?
C1 C3 C5 121.03(14) . . ?
C1 C3 C2 121.43(16) . . ?
C2 C3 C5 117.22(14) . . ?
C3 C1 H1A 119.1(9) . . ?
C3 C1 H1B 124.5(12) . . ?
H1A C1 H1B 113.1(15) . . ?
C3 C2 H2A 118.7(11) . . ?
C3 C2 H2B 112.7(10) . . ?
C3 C2 H2C 107.2(19) . . ?
H2A C2 H2B 110.3(14) . . ?
H2A C2 H2C 95(2) . . ?
H2B C2 H2C 111(2) . . ?
C17 C15 H15A 121.8(9) . . ?
C17 C15 H15B 119.6(9) . . ?
H15A C15 H15B 118.6(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
O1 C5 C6 N1 -55.48(14) . . . . ?
O1 C5 C3 C1 148.17(14) . . . . ?
O1 C5 C3 C2 -38.27(18) . . . . ?
O6 N4 C28 C26 178.57(11) . . . . ?
O6 N4 C28 C27 0.04(17) . . . . ?
O3 N2 C14 C13 2.41(17) . . . . ?
O3 N2 C14 C12 -176.94(11) . . . . ?
O4 C19 C20 N3 56.03(15) . . . . ?
O4 C19 C17 C16 46.99(16) . . . . ?
O4 C19 C17 C15 -136.26(14) . . . . ?
O4 C21 C22 N3 -54.94(15) . . . . ?
O2 N2 C14 C13 -177.36(11) . . . . ?
O2 N2 C14 C12 3.29(17) . . . . ?
O5 N4 C28 C26 -0.55(17) . . . . ?
O5 N4 C28 C27 -179.08(11) . . . . ?
N3 C23 C24 C26 -177.62(11) . . . . ?
N3 C23 C25 C27 177.51(11) . . . . ?
N1 C8 C7 O1 55.28(15) . . . . ?
N4 C28 C26 C24 -179.15(11) . . . . ?
N4 C28 C27 C25 179.05(11) . . . . ?
C13 C11 C9 N1 -179.19(12) . . . . ?
C13 C11 C9 C10 -0.78(18) . . . . ?
C28 C26 C24 C23 0.21(18) . . . . ?
C28 C27 C25 C23 -0.01(18) . . . . ?
C12 C10 C9 N1 179.75(12) . . . . ?
C12 C10 C9 C11 1.32(18) . . . . ?
C26 C28 C27 C25 0.55(19) . . . . ?
C14 C13 C11 C9 -0.01(19) . . . . ?
C14 C12 C10 C9 -1.1(2) . . . . ?
C27 C28 C26 C24 -0.65(18) . . . . ?
C23 N3 C20 C19 162.76(11) . . . . ?
C23 N3 C22 C21 -165.36(11) . . . . ?
C24 C23 C25 C27 -0.41(17) . . . . ?
C5 O1 C7 C8 -58.48(14) . . . . ?
C10 C12 C14 N2 179.57(12) . . . . ?
C10 C12 C14 C13 0.22(19) . . . . ?
C11 C13 C14 N2 -179.03(12) . . . . ?
C11 C13 C14 C12 0.31(19) . . . . ?
C25 C23 C24 C26 0.30(18) . . . . ?
C9 N1 C6 C5 -165.62(11) . . . . ?
C9 N1 C8 C7 168.16(11) . . . . ?
C19 O4 C21 C22 60.25(14) . . . . ?
C20 N3 C23 C24 -33.60(17) . . . . ?
C20 N3 C23 C25 148.56(12) . . . . ?
C20 N3 C22 C21 50.78(15) . . . . ?
C20 C19 C17 C16 168.92(13) . . . . ?
C20 C19 C17 C15 -14.3(2) . . . . ?
C6 N1 C9 C10 35.33(17) . . . . ?
C6 N1 C9 C11 -146.32(12) . . . . ?
C6 N1 C8 C7 -51.99(14) . . . . ?
C6 C5 C3 C1 25.34(19) . . . . ?
C6 C5 C3 C2 -161.11(15) . . . . ?
C17 C19 C20 N3 -66.92(16) . . . . ?
C8 N1 C9 C10 172.39(11) . . . . ?
C8 N1 C9 C11 -9.26(18) . . . . ?
C8 N1 C6 C5 54.16(14) . . . . ?
C7 O1 C5 C6 56.73(14) . . . . ?
C7 O1 C5 C4 171.70(11) . . . . ?
C7 O1 C5 C3 -69.45(13) . . . . ?
C18 C19 C20 N3 169.14(12) . . . . ?
C18 C19 C17 C16 -68.03(17) . . . . ?
C18 C19 C17 C15 108.73(16) . . . . ?
C21 O4 C19 C20 -58.99(14) . . . . ?
C21 O4 C19 C17 66.59(13) . . . . ?
C21 O4 C19 C18 -174.81(11) . . . . ?
C4 C5 C6 N1 -168.89(11) . . . . ?
C4 C5 C3 C1 -95.90(17) . . . . ?
C4 C5 C3 C2 77.65(18) . . . . ?
C22 N3 C23 C24 -174.84(11) . . . . ?
C22 N3 C23 C25 7.32(17) . . . . ?
C22 N3 C20 C19 -53.44(15) . . . . ?
C3 C5 C6 N1 68.57(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
