# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_Compuesto_3b
_database_code_depnum_ccdc_archive 'CCDC 2189449'
loop_
_audit_author_name
_audit_author_address
'Ruben A Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2022-07-11 deposited with the CCDC.	2024-04-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 N4'
_chemical_formula_sum            'C18 H16 N4'
_chemical_formula_weight         288.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.0543(16)
_cell_length_b                   7.6061(11)
_cell_length_c                   18.348(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.582(3)
_cell_angle_gamma                90
_cell_volume                     1529.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6064
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      29.60

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6411
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            27078
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.293
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8575
_reflns_number_gt                4185
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.998

_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.
;

_computing_data_collection       'APEX3 v2019.1-0(Bruker, 2019)'
_computing_cell_refinement       'APEX3 v2019.1-0(Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0569P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0070(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
?
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration unk
_refine_ls_number_reflns         8575
_refine_ls_number_parameters     400
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1416
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8433(3) 0.7875(4) 0.06835(15) 0.0527(8) Uani 1 1 d . . . . .
N2 N 0.8906(3) 0.7592(4) 0.19681(15) 0.0506(7) Uani 1 1 d . . . . .
N3 N 0.9672(3) 0.6980(4) 0.24850(15) 0.0543(8) Uani 1 1 d . . . . .
C1 C 0.7268(4) 0.8724(6) 0.0724(2) 0.0747(13) Uani 1 1 d . . . . .
H1A H 0.668836 0.786704 0.084490 0.112 Uiso 1 1 calc R U . . .
H1B H 0.697762 0.924729 0.025734 0.112 Uiso 1 1 calc R U . . .
H1C H 0.736637 0.961853 0.109595 0.112 Uiso 1 1 calc R U . . .
C2 C 0.9231(3) 0.7292(5) 0.12754(17) 0.0486(9) Uani 1 1 d . . . . .
C3 C 1.0188(3) 0.6466(6) 0.10092(19) 0.0609(10) Uani 1 1 d . . . . .
H3 H 1.085901 0.595048 0.128771 0.073 Uiso 1 1 calc R U . . .
C4 C 0.9969(4) 0.6546(6) 0.02498(19) 0.0651(11) Uani 1 1 d . . . . .
H4 H 1.046537 0.608955 -0.007561 0.078 Uiso 1 1 calc R U . . .
C5 C 0.8893(3) 0.7415(6) 0.00644(18) 0.0587(10) Uani 1 1 d . . . . .
H5 H 0.853308 0.765258 -0.041259 0.070 Uiso 1 1 calc R U . . .
C6 C 0.8789(3) 0.7502(5) 0.46441(17) 0.0453(8) Uani 1 1 d . . . . .
C7 C 0.8034(3) 0.8262(5) 0.40612(18) 0.0547(10) Uani 1 1 d . . . . .
H7 H 0.734099 0.886720 0.415614 0.066 Uiso 1 1 calc R U . . .
C8 C 0.8288(3) 0.8142(6) 0.33465(18) 0.0562(10) Uani 1 1 d . . . . .
H8 H 0.776800 0.866061 0.296726 0.067 Uiso 1 1 calc R U . . .
C9 C 0.9320(3) 0.7247(5) 0.31930(17) 0.0473(9) Uani 1 1 d . . . . .
C10 C 1.0098(3) 0.6539(5) 0.37728(18) 0.0525(9) Uani 1 1 d . . . . .
H10 H 1.080984 0.598058 0.367946 0.063 Uiso 1 1 calc R U . . .
C11 C 0.9838(3) 0.6647(5) 0.44824(17) 0.0509(9) Uani 1 1 d . . . . .
H11 H 1.036750 0.614209 0.486069 0.061 Uiso 1 1 calc R U . . .
C12 C 0.8459(3) 0.7610(5) 0.53881(17) 0.0499(9) Uani 1 1 d . . . . .
H12 H 0.774387 0.821460 0.543869 0.060 Uiso 1 1 calc R U . . .
C13 C 0.9059(3) 0.6949(5) 0.59973(18) 0.0523(10) Uani 1 1 d . . . . .
H13 H 0.976100 0.630905 0.595080 0.063 Uiso 1 1 calc R U . . .
C14 C 0.8720(3) 0.7131(5) 0.67405(17) 0.0486(9) Uani 1 1 d . . . . .
C15 C 0.9514(3) 0.6609(6) 0.73457(18) 0.0614(11) Uani 1 1 d . . . . .
H15 H 1.027058 0.613195 0.728915 0.074 Uiso 1 1 calc R U . . .
C16 C 0.9166(4) 0.6806(6) 0.8037(2) 0.0715(12) Uani 1 1 d . . . . .
H16 H 0.971894 0.644884 0.843599 0.086 Uiso 1 1 calc R U . . .
N17 N 0.8115(3) 0.7457(5) 0.81806(16) 0.0696(10) Uani 1 1 d . . . . .
C18 C 0.7367(4) 0.7951(6) 0.7594(2) 0.0685(13) Uani 1 1 d . . . . .
H18 H 0.661523 0.841575 0.766922 0.082 Uiso 1 1 calc R U . . .
C19 C 0.7614(3) 0.7830(6) 0.68849(19) 0.0627(12) Uani 1 1 d . . . . .
H19 H 0.704312 0.821385 0.649983 0.075 Uiso 1 1 calc R U . . .
N21 N 0.4285(3) 0.7433(4) 0.90173(15) 0.0527(7) Uani 1 1 d . . . . .
N22 N 0.3806(3) 0.7445(4) 0.77286(15) 0.0511(8) Uani 1 1 d . . . . .
N23 N 0.3009(3) 0.7903(4) 0.71966(15) 0.0535(8) Uani 1 1 d . . . . .
C21 C 0.5492(3) 0.6748(6) 0.9014(2) 0.0757(13) Uani 1 1 d . . . . .
H21A H 0.603811 0.768953 0.893476 0.114 Uiso 1 1 calc R U . . .
H21B H 0.548673 0.589792 0.862641 0.114 Uiso 1 1 calc R U . . .
H21C H 0.576014 0.619613 0.947762 0.114 Uiso 1 1 calc R U . . .
C22 C 0.3454(3) 0.7784(5) 0.84073(18) 0.0494(9) Uani 1 1 d . . . . .
C23 C 0.2426(4) 0.8485(5) 0.8642(2) 0.0619(10) Uani 1 1 d . . . . .
H23 H 0.172375 0.884756 0.834454 0.074 Uiso 1 1 calc R U . . .
C24 C 0.2628(4) 0.8552(6) 0.9400(2) 0.0690(11) Uani 1 1 d . . . . .
H24 H 0.208096 0.896014 0.970534 0.083 Uiso 1 1 calc R U . . .
C25 C 0.3775(4) 0.7911(6) 0.9623(2) 0.0636(11) Uani 1 1 d . . . . .
H25 H 0.414400 0.781875 1.010712 0.076 Uiso 1 1 calc R U . . .
C26 C 0.3882(3) 0.7206(5) 0.50453(17) 0.0479(9) Uani 1 1 d . . . . .
C27 C 0.4648(3) 0.6512(5) 0.56454(19) 0.0534(9) Uani 1 1 d . . . . .
H27 H 0.534609 0.590729 0.555943 0.064 Uiso 1 1 calc R U . . .
C28 C 0.4403(3) 0.6692(5) 0.63557(18) 0.0518(9) Uani 1 1 d . . . . .
H28 H 0.492636 0.620790 0.674216 0.062 Uiso 1 1 calc R U . . .
C29 C 0.3367(3) 0.7605(5) 0.64929(18) 0.0477(9) Uani 1 1 d . . . . .
C30 C 0.2600(3) 0.8292(6) 0.59082(19) 0.0574(10) Uani 1 1 d . . . . .
H30 H 0.189866 0.888759 0.599579 0.069 Uiso 1 1 calc R U . . .
C31 C 0.2852(3) 0.8113(5) 0.52025(19) 0.0570(10) Uani 1 1 d . . . . .
H31 H 0.232548 0.860572 0.481958 0.068 Uiso 1 1 calc R U . . .
C32 C 0.4190(3) 0.6973(5) 0.43042(19) 0.0545(10) Uani 1 1 d . . . . .
H32 H 0.490918 0.636971 0.426279 0.065 Uiso 1 1 calc R U . . .
C33 C 0.3555(3) 0.7528(6) 0.36787(19) 0.0559(10) Uani 1 1 d . . . . .
H33 H 0.281806 0.808634 0.371733 0.067 Uiso 1 1 calc R U . . .
C34 C 0.3892(3) 0.7354(5) 0.29393(18) 0.0530(9) Uani 1 1 d . . . . .
C35 C 0.3060(4) 0.7760(6) 0.2335(2) 0.0688(13) Uani 1 1 d . . . . .
H35 H 0.227858 0.813519 0.239618 0.083 Uiso 1 1 calc R U . . .
C36 C 0.3392(4) 0.7605(8) 0.1644(2) 0.0845(15) Uani 1 1 d . . . . .
H36 H 0.280651 0.787119 0.124782 0.101 Uiso 1 1 calc R U . . .
N37 N 0.4482(3) 0.7106(6) 0.14971(17) 0.0768(11) Uani 1 1 d . . . . .
C38 C 0.5286(4) 0.6737(6) 0.2084(2) 0.0687(12) Uani 1 1 d . . . . .
H38 H 0.606437 0.638453 0.200582 0.082 Uiso 1 1 calc R U . . .
C39 C 0.5042(3) 0.6842(5) 0.2795(2) 0.0603(10) Uani 1 1 d . . . . .
H39 H 0.564641 0.657154 0.318065 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
N1 C5 1.351(4) . ?
N1 C2 1.379(4) . ?
N1 C1 1.451(5) . ?
N2 N3 1.273(3) . ?
N2 C2 1.385(4) . ?
N3 C9 1.419(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.375(5) . ?
C3 C4 1.384(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.393(4) . ?
C6 C11 1.394(4) . ?
C6 C12 1.461(4) . ?
C7 C8 1.380(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.389(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(4) . ?
C10 C11 1.373(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.321(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.467(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(4) . ?
C14 C19 1.390(5) . ?
C15 C16 1.382(5) . ?
C15 H15 0.9300 . ?
C16 N17 1.321(5) . ?
C16 H16 0.9300 . ?
N17 C18 1.323(4) . ?
C18 C19 1.367(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N21 C25 1.360(4) . ?
N21 C22 1.377(4) . ?
N21 C21 1.434(4) . ?
N22 N23 1.274(3) . ?
N22 C22 1.377(4) . ?
N23 C29 1.418(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.375(5) . ?
C23 C24 1.380(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C31 1.393(5) . ?
C26 C27 1.401(4) . ?
C26 C32 1.455(4) . ?
C27 C28 1.372(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.390(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.380(4) . ?
C30 C31 1.367(5) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C33 1.332(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.459(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.379(5) . ?
C34 C39 1.388(5) . ?
C35 C36 1.371(5) . ?
C35 H35 0.9300 . ?
C36 N37 1.324(5) . ?
C36 H36 0.9300 . ?
N37 C38 1.334(5) . ?
C38 C39 1.368(5) . ?
C38 H38 0.9300 . ?
C39 H39 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
C5 N1 C2 107.8(3) . . ?
C5 N1 C1 126.4(3) . . ?
C2 N1 C1 125.6(3) . . ?
N3 N2 C2 113.3(3) . . ?
N2 N3 C9 113.2(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 108.0(3) . . ?
C3 C2 N2 135.0(3) . . ?
N1 C2 N2 117.0(3) . . ?
C2 C3 C4 107.3(3) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
C5 C4 C3 107.7(3) . . ?
C5 C4 H4 126.2 . . ?
C3 C4 H4 126.2 . . ?
N1 C5 C4 109.2(3) . . ?
N1 C5 H5 125.4 . . ?
C4 C5 H5 125.4 . . ?
C7 C6 C11 117.5(3) . . ?
C7 C6 C12 119.7(3) . . ?
C11 C6 C12 122.8(3) . . ?
C8 C7 C6 121.7(3) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 N3 115.5(3) . . ?
C8 C9 N3 125.9(3) . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C6 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C13 C12 C6 127.6(3) . . ?
C13 C12 H12 116.2 . . ?
C6 C12 H12 116.2 . . ?
C12 C13 C14 126.1(4) . . ?
C12 C13 H13 116.9 . . ?
C14 C13 H13 116.9 . . ?
C15 C14 C19 116.0(3) . . ?
C15 C14 C13 120.5(3) . . ?
C19 C14 C13 123.5(3) . . ?
C14 C15 C16 118.9(4) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
N17 C16 C15 125.6(4) . . ?
N17 C16 H16 117.2 . . ?
C15 C16 H16 117.2 . . ?
C16 N17 C18 114.6(3) . . ?
N17 C18 C19 125.0(4) . . ?
N17 C18 H18 117.5 . . ?
C19 C18 H18 117.5 . . ?
C18 C19 C14 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C25 N21 C22 108.0(3) . . ?
C25 N21 C21 126.0(3) . . ?
C22 N21 C21 126.0(3) . . ?
N23 N22 C22 113.1(3) . . ?
N22 N23 C29 113.9(3) . . ?
N21 C21 H21A 109.5 . . ?
N21 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N21 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 N22 134.4(3) . . ?
C23 C22 N21 108.1(3) . . ?
N22 C22 N21 117.4(3) . . ?
C22 C23 C24 107.4(4) . . ?
C22 C23 H23 126.3 . . ?
C24 C23 H23 126.3 . . ?
C25 C24 C23 107.9(4) . . ?
C25 C24 H24 126.0 . . ?
C23 C24 H24 126.0 . . ?
N21 C25 C24 108.6(3) . . ?
N21 C25 H25 125.7 . . ?
C24 C25 H25 125.7 . . ?
C31 C26 C27 116.7(3) . . ?
C31 C26 C32 123.5(3) . . ?
C27 C26 C32 119.8(3) . . ?
C28 C27 C26 122.3(3) . . ?
C28 C27 H27 118.8 . . ?
C26 C27 H27 118.8 . . ?
C27 C28 C29 119.5(3) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C30 C29 C28 119.0(3) . . ?
C30 C29 N23 115.5(3) . . ?
C28 C29 N23 125.5(3) . . ?
C31 C30 C29 121.2(4) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C30 C31 C26 121.3(3) . . ?
C30 C31 H31 119.3 . . ?
C26 C31 H31 119.3 . . ?
C33 C32 C26 127.2(4) . . ?
C33 C32 H32 116.4 . . ?
C26 C32 H32 116.4 . . ?
C32 C33 C34 127.0(4) . . ?
C32 C33 H33 116.5 . . ?
C34 C33 H33 116.5 . . ?
C35 C34 C39 116.1(3) . . ?
C35 C34 C33 120.1(3) . . ?
C39 C34 C33 123.7(3) . . ?
C36 C35 C34 119.5(4) . . ?
C36 C35 H35 120.3 . . ?
C34 C35 H35 120.3 . . ?
N37 C36 C35 125.1(4) . . ?
N37 C36 H36 117.4 . . ?
C35 C36 H36 117.4 . . ?
C36 N37 C38 115.0(3) . . ?
N37 C38 C39 124.3(4) . . ?
N37 C38 H38 117.9 . . ?
C39 C38 H38 117.9 . . ?
C38 C39 C34 119.9(4) . . ?
C38 C39 H39 120.0 . . ?
C34 C39 H39 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
C2 N2 N3 C9 -178.4(3) . . . . ?
C5 N1 C2 C3 0.0(4) . . . . ?
C1 N1 C2 C3 176.2(4) . . . . ?
C5 N1 C2 N2 -178.2(3) . . . . ?
C1 N1 C2 N2 -2.1(6) . . . . ?
N3 N2 C2 C3 0.8(6) . . . . ?
N3 N2 C2 N1 178.4(3) . . . . ?
N1 C2 C3 C4 -0.1(5) . . . . ?
N2 C2 C3 C4 177.7(4) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C2 N1 C5 C4 0.1(4) . . . . ?
C1 N1 C5 C4 -176.0(4) . . . . ?
C3 C4 C5 N1 -0.2(5) . . . . ?
C11 C6 C7 C8 1.7(6) . . . . ?
C12 C6 C7 C8 -177.8(3) . . . . ?
C6 C7 C8 C9 -0.1(6) . . . . ?
C7 C8 C9 C10 -2.1(6) . . . . ?
C7 C8 C9 N3 178.1(4) . . . . ?
N2 N3 C9 C10 177.4(3) . . . . ?
N2 N3 C9 C8 -2.8(6) . . . . ?
C8 C9 C10 C11 2.7(6) . . . . ?
N3 C9 C10 C11 -177.5(3) . . . . ?
C9 C10 C11 C6 -1.1(6) . . . . ?
C7 C6 C11 C10 -1.1(5) . . . . ?
C12 C6 C11 C10 178.4(3) . . . . ?
C7 C6 C12 C13 179.1(4) . . . . ?
C11 C6 C12 C13 -0.3(6) . . . . ?
C6 C12 C13 C14 177.9(3) . . . . ?
C12 C13 C14 C15 -170.2(4) . . . . ?
C12 C13 C14 C19 9.4(6) . . . . ?
C19 C14 C15 C16 0.1(6) . . . . ?
C13 C14 C15 C16 179.8(4) . . . . ?
C14 C15 C16 N17 0.3(7) . . . . ?
C15 C16 N17 C18 -0.3(7) . . . . ?
C16 N17 C18 C19 -0.1(7) . . . . ?
N17 C18 C19 C14 0.5(7) . . . . ?
C15 C14 C19 C18 -0.5(6) . . . . ?
C13 C14 C19 C18 179.9(4) . . . . ?
C22 N22 N23 C29 178.5(3) . . . . ?
N23 N22 C22 C23 1.1(6) . . . . ?
N23 N22 C22 N21 -176.2(3) . . . . ?
C25 N21 C22 C23 0.0(4) . . . . ?
C21 N21 C22 C23 -177.8(4) . . . . ?
C25 N21 C22 N22 178.0(3) . . . . ?
C21 N21 C22 N22 0.2(6) . . . . ?
N22 C22 C23 C24 -177.8(4) . . . . ?
N21 C22 C23 C24 -0.4(5) . . . . ?
C22 C23 C24 C25 0.6(5) . . . . ?
C22 N21 C25 C24 0.3(4) . . . . ?
C21 N21 C25 C24 178.1(4) . . . . ?
C23 C24 C25 N21 -0.5(5) . . . . ?
C31 C26 C27 C28 0.5(6) . . . . ?
C32 C26 C27 C28 180.0(3) . . . . ?
C26 C27 C28 C29 -0.5(6) . . . . ?
C27 C28 C29 C30 0.8(5) . . . . ?
C27 C28 C29 N23 -179.5(3) . . . . ?
N22 N23 C29 C30 -171.9(3) . . . . ?
N22 N23 C29 C28 8.4(5) . . . . ?
C28 C29 C30 C31 -1.0(6) . . . . ?
N23 C29 C30 C31 179.2(3) . . . . ?
C29 C30 C31 C26 1.0(6) . . . . ?
C27 C26 C31 C30 -0.7(6) . . . . ?
C32 C26 C31 C30 179.8(4) . . . . ?
C31 C26 C32 C33 -1.5(6) . . . . ?
C27 C26 C32 C33 179.1(4) . . . . ?
C26 C32 C33 C34 177.3(4) . . . . ?
C32 C33 C34 C35 170.4(4) . . . . ?
C32 C33 C34 C39 -11.7(6) . . . . ?
C39 C34 C35 C36 1.4(7) . . . . ?
C33 C34 C35 C36 179.4(4) . . . . ?
C34 C35 C36 N37 -0.9(8) . . . . ?
C35 C36 N37 C38 0.1(8) . . . . ?
C36 N37 C38 C39 0.2(7) . . . . ?
N37 C38 C39 C34 0.3(7) . . . . ?
C35 C34 C39 C38 -1.1(6) . . . . ?
C33 C34 C39 C38 -179.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 N17 0.93 2.57 3.450(5) 159.0 1_554 yes
C25 H25 N37 0.93 2.59 3.479(5) 161.1 1_556 yes

_refine_diff_density_max         0.140
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035

