# Supplementary Information (SI) for CrystEngComm.
# 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_kn241211d_1_a
_database_code_depnum_ccdc_archive 'CCDC 2419629'
loop_
_audit_author_name
_audit_author_address
'Akiko Hori'
;Shibaura Institute of Technology
Japan
;
_audit_update_record             
;
2025-01-25 deposited with the CCDC.	2025-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H10 N6, C10 H8'
_chemical_formula_sum            'C30 H18 N6'
_chemical_formula_weight         462.50

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.0115(15)
_cell_length_b                   7.1139(7)
_cell_length_c                   24.401(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.624(4)
_cell_angle_gamma                90
_cell_volume                     2373.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    160
_cell_measurement_reflns_used    6189
_cell_measurement_theta_min      2.5019
_cell_measurement_theta_max      26.0379

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.253
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Goniometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            25961
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.980
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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             4199
_reflns_number_gt                3290
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebshle, rev 924)'
_computing_publication_material  ?
_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)+(0.0523P)²+0.7012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0095(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4199
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.27408(11) 0.6200(2) 0.38231(7) 0.0343(4) Uani 1 1 d . . . . .
C2 C 0.27605(11) 0.5733(2) 0.32430(7) 0.0337(4) Uani 1 1 d . . . . .
C3 C 0.44095(11) 0.6280(2) 0.40337(7) 0.0336(4) Uani 1 1 d . . . . .
C4 C 0.44267(11) 0.5669(2) 0.34866(7) 0.0332(4) Uani 1 1 d . . . . .
C5 C 0.60608(12) 0.6414(2) 0.42473(7) 0.0401(4) Uani 1 1 d . . . . .
C6 C 0.60773(12) 0.5768(2) 0.36983(7) 0.0390(4) Uani 1 1 d . . . . .
C7 C 0.69706(13) 0.6857(3) 0.46364(8) 0.0488(5) Uani 1 1 d . . . . .
C8 C 0.70020(13) 0.5516(3) 0.35342(8) 0.0480(5) Uani 1 1 d . . . . .
C9 C 0.18200(11) 0.6380(2) 0.40282(7) 0.0385(4) Uani 1 1 d . . . . .
C10 C 0.10723(12) 0.5071(3) 0.38902(7) 0.0468(5) Uani 1 1 d . . . . .
H10 H 0.113266 0.405422 0.364753 0.056 Uiso 1 1 calc R U . . .
C11 C 0.02392(13) 0.5235(3) 0.41037(9) 0.0577(6) Uani 1 1 d . . . . .
H11 H -0.026747 0.432701 0.401080 0.069 Uiso 1 1 calc R U . . .
C12 C 0.01452(14) 0.6719(4) 0.44516(9) 0.0640(6) Uani 1 1 d . . . . .
H12 H -0.042877 0.683577 0.459637 0.077 Uiso 1 1 calc R U . . .
C13 C 0.08794(15) 0.8031(3) 0.45898(8) 0.0605(6) Uani 1 1 d . . . . .
H13 H 0.080800 0.905782 0.482637 0.073 Uiso 1 1 calc R U . . .
C14 C 0.17231(13) 0.7859(3) 0.43850(7) 0.0477(5) Uani 1 1 d . . . . .
H14 H 0.223531 0.875094 0.448831 0.057 Uiso 1 1 calc R U . . .
C15 C 0.18787(11) 0.5661(2) 0.27750(7) 0.0362(4) Uani 1 1 d . . . . .
C16 C 0.18304(12) 0.4318(3) 0.23562(7) 0.0422(4) Uani 1 1 d . . . . .
H16 H 0.232977 0.339598 0.238767 0.051 Uiso 1 1 calc R U . . .
C17 C 0.10548(13) 0.4321(3) 0.18920(8) 0.0494(5) Uani 1 1 d . . . . .
H17 H 0.101770 0.338395 0.161079 0.059 Uiso 1 1 calc R U . . .
C18 C 0.03408(13) 0.5674(3) 0.18376(8) 0.0517(5) Uani 1 1 d . . . . .
H18 H -0.018219 0.568522 0.151562 0.062 Uiso 1 1 calc R U . . .
C19 C 0.03830(13) 0.7016(3) 0.22507(8) 0.0527(5) Uani 1 1 d . . . . .
H19 H -0.011138 0.795094 0.221192 0.063 Uiso 1 1 calc R U . . .
C20 C 0.11433(12) 0.7006(3) 0.27217(7) 0.0451(4) Uani 1 1 d . . . . .
H20 H 0.116228 0.791768 0.300828 0.054 Uiso 1 1 calc R U . . .
C21 C 0.66858(19) 0.1418(3) 0.42010(10) 0.0710(6) Uani 1 1 d . . . . .
H21 H 0.728082 0.168773 0.446066 0.085 Uiso 1 1 calc R U . . .
C22 C 0.58241(19) 0.1612(3) 0.43608(8) 0.0637(6) Uani 1 1 d . . . . .
H22 H 0.582238 0.200399 0.473279 0.076 Uiso 1 1 calc R U . . .
C23 C 0.49251(16) 0.1238(3) 0.39804(8) 0.0532(5) Uani 1 1 d . . . . .
C24 C 0.4020(2) 0.1480(3) 0.41224(12) 0.0759(7) Uani 1 1 d . . . . .
H24 H 0.399450 0.188183 0.449019 0.091 Uiso 1 1 calc R U . . .
C25 C 0.3176(2) 0.1147(4) 0.37391(17) 0.0938(10) Uani 1 1 d . . . . .
H25 H 0.256447 0.134305 0.383788 0.113 Uiso 1 1 calc R U . . .
C26 C 0.3204(2) 0.0507(4) 0.31918(15) 0.0908(9) Uani 1 1 d . . . . .
H26 H 0.261094 0.025459 0.292824 0.109 Uiso 1 1 calc R U . . .
C27 C 0.4072(2) 0.0253(3) 0.30434(10) 0.0731(7) Uani 1 1 d . . . . .
H27 H 0.408316 -0.017779 0.267644 0.088 Uiso 1 1 calc R U . . .
C28 C 0.49502(16) 0.0621(3) 0.34255(8) 0.0531(5) Uani 1 1 d . . . . .
C29 C 0.58728(19) 0.0432(3) 0.32855(9) 0.0651(6) Uani 1 1 d . . . . .
H29 H 0.590549 0.001694 0.291997 0.078 Uiso 1 1 calc R U . . .
C30 C 0.6708(2) 0.0830(3) 0.36616(11) 0.0740(7) Uani 1 1 d . . . . .
H30 H 0.731864 0.070643 0.355576 0.089 Uiso 1 1 calc R U . . .
N1 N 0.35535(9) 0.64971(19) 0.42022(5) 0.0369(3) Uani 1 1 d . . . . .
N2 N 0.35908(9) 0.54101(19) 0.30935(5) 0.0354(3) Uani 1 1 d . . . . .
N3 N 0.52414(9) 0.6664(2) 0.44190(6) 0.0395(3) Uani 1 1 d . . . . .
N4 N 0.52761(9) 0.5386(2) 0.33194(6) 0.0384(3) Uani 1 1 d . . . . .
N5 N 0.76998(12) 0.7230(3) 0.49310(8) 0.0689(5) Uani 1 1 d . . . . .
N6 N 0.77369(12) 0.5338(3) 0.34089(8) 0.0688(5) Uani 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
C1 N1 1.318(2) . ?
C1 C2 1.460(2) . ?
C1 C9 1.488(2) . ?
C2 N2 1.313(2) . ?
C2 C15 1.489(2) . ?
C3 N3 1.356(2) . ?
C3 N1 1.359(2) . ?
C3 C4 1.409(2) . ?
C4 N2 1.355(2) . ?
C4 N4 1.355(2) . ?
C5 N3 1.318(2) . ?
C5 C6 1.421(2) . ?
C5 C7 1.448(2) . ?
C6 N4 1.317(2) . ?
C6 C8 1.448(2) . ?
C7 N5 1.144(2) . ?
C8 N6 1.143(2) . ?
C9 C10 1.387(2) . ?
C9 C14 1.391(2) . ?
C10 C11 1.383(3) . ?
C11 C12 1.379(3) . ?
C12 C13 1.375(3) . ?
C13 C14 1.386(3) . ?
C15 C16 1.390(2) . ?
C15 C20 1.391(2) . ?
C16 C17 1.388(2) . ?
C17 C18 1.373(3) . ?
C18 C19 1.380(3) . ?
C19 C20 1.386(2) . ?
C21 C22 1.355(3) . ?
C21 C30 1.388(3) . ?
C22 C23 1.417(3) . ?
C23 C24 1.396(3) . ?
C23 C28 1.431(3) . ?
C24 C25 1.359(4) . ?
C25 C26 1.420(4) . ?
C26 C27 1.354(4) . ?
C27 C28 1.397(3) . ?
C28 C29 1.414(3) . ?
C29 C30 1.350(3) . ?

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
N1 C1 C2 121.36(14) . . ?
N1 C1 C9 115.48(14) . . ?
C2 C1 C9 123.17(13) . . ?
N2 C2 C1 120.98(14) . . ?
N2 C2 C15 114.70(14) . . ?
C1 C2 C15 124.27(13) . . ?
N3 C3 N1 116.69(14) . . ?
N3 C3 C4 121.94(14) . . ?
N1 C3 C4 121.37(14) . . ?
N2 C4 N4 116.54(14) . . ?
N2 C4 C3 121.45(14) . . ?
N4 C4 C3 121.95(14) . . ?
N3 C5 C6 122.58(15) . . ?
N3 C5 C7 117.73(16) . . ?
C6 C5 C7 119.68(15) . . ?
N4 C6 C5 122.78(15) . . ?
N4 C6 C8 117.18(15) . . ?
C5 C6 C8 120.03(15) . . ?
N5 C7 C5 178.0(2) . . ?
N6 C8 C6 179.1(2) . . ?
C10 C9 C14 119.19(16) . . ?
C10 C9 C1 121.69(16) . . ?
C14 C9 C1 119.07(15) . . ?
C11 C10 C9 120.43(19) . . ?
C12 C11 C10 119.92(19) . . ?
C13 C12 C11 120.22(18) . . ?
C12 C13 C14 120.2(2) . . ?
C13 C14 C9 120.01(19) . . ?
C16 C15 C20 119.19(15) . . ?
C16 C15 C2 119.12(15) . . ?
C20 C15 C2 121.45(15) . . ?
C17 C16 C15 120.19(16) . . ?
C18 C17 C16 120.26(17) . . ?
C17 C18 C19 120.00(16) . . ?
C18 C19 C20 120.30(17) . . ?
C19 C20 C15 120.04(17) . . ?
C22 C21 C30 120.7(2) . . ?
C21 C22 C23 120.85(19) . . ?
C24 C23 C22 122.6(2) . . ?
C24 C23 C28 119.0(2) . . ?
C22 C23 C28 118.38(19) . . ?
C25 C24 C23 120.6(3) . . ?
C24 C25 C26 120.3(3) . . ?
C27 C26 C25 120.3(3) . . ?
C26 C27 C28 120.6(3) . . ?
C27 C28 C29 122.7(2) . . ?
C27 C28 C23 119.3(2) . . ?
C29 C28 C23 118.08(19) . . ?
C30 C29 C28 121.2(2) . . ?
C29 C30 C21 120.8(2) . . ?
C1 N1 C3 117.00(13) . . ?
C2 N2 C4 117.44(13) . . ?
C5 N3 C3 115.40(14) . . ?
C6 N4 C4 115.32(14) . . ?

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 C1 C2 N2 6.8(2) . . . . ?
C9 C1 C2 N2 -173.32(15) . . . . ?
N1 C1 C2 C15 -170.42(15) . . . . ?
C9 C1 C2 C15 9.4(2) . . . . ?
N3 C3 C4 N2 -175.51(15) . . . . ?
N1 C3 C4 N2 5.1(2) . . . . ?
N3 C3 C4 N4 1.7(2) . . . . ?
N1 C3 C4 N4 -177.72(14) . . . . ?
N3 C5 C6 N4 0.5(3) . . . . ?
C7 C5 C6 N4 -178.22(16) . . . . ?
N3 C5 C6 C8 -179.88(16) . . . . ?
C7 C5 C6 C8 1.4(3) . . . . ?
N1 C1 C9 C10 -134.98(17) . . . . ?
C2 C1 C9 C10 45.2(2) . . . . ?
N1 C1 C9 C14 42.5(2) . . . . ?
C2 C1 C9 C14 -137.38(17) . . . . ?
C14 C9 C10 C11 0.1(3) . . . . ?
C1 C9 C10 C11 177.61(16) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C9 1.5(3) . . . . ?
C10 C9 C14 C13 -1.2(3) . . . . ?
C1 C9 C14 C13 -178.72(16) . . . . ?
N2 C2 C15 C16 38.2(2) . . . . ?
C1 C2 C15 C16 -144.45(17) . . . . ?
N2 C2 C15 C20 -136.17(17) . . . . ?
C1 C2 C15 C20 41.2(2) . . . . ?
C20 C15 C16 C17 -0.2(3) . . . . ?
C2 C15 C16 C17 -174.67(16) . . . . ?
C15 C16 C17 C18 1.4(3) . . . . ?
C16 C17 C18 C19 -1.2(3) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C18 C19 C20 C15 1.2(3) . . . . ?
C16 C15 C20 C19 -1.1(3) . . . . ?
C2 C15 C20 C19 173.25(16) . . . . ?
C30 C21 C22 C23 -0.6(3) . . . . ?
C21 C22 C23 C24 -177.8(2) . . . . ?
C21 C22 C23 C28 1.0(3) . . . . ?
C22 C23 C24 C25 178.4(2) . . . . ?
C28 C23 C24 C25 -0.4(3) . . . . ?
C23 C24 C25 C26 1.4(4) . . . . ?
C24 C25 C26 C27 -1.1(4) . . . . ?
C25 C26 C27 C28 -0.1(3) . . . . ?
C26 C27 C28 C29 -178.1(2) . . . . ?
C26 C27 C28 C23 1.1(3) . . . . ?
C24 C23 C28 C27 -0.9(3) . . . . ?
C22 C23 C28 C27 -179.69(18) . . . . ?
C24 C23 C28 C29 178.35(18) . . . . ?
C22 C23 C28 C29 -0.5(3) . . . . ?
C27 C28 C29 C30 178.8(2) . . . . ?
C23 C28 C29 C30 -0.4(3) . . . . ?
C28 C29 C30 C21 0.8(3) . . . . ?
C22 C21 C30 C29 -0.3(4) . . . . ?
C2 C1 N1 C3 -2.4(2) . . . . ?
C9 C1 N1 C3 177.77(14) . . . . ?
N3 C3 N1 C1 177.31(14) . . . . ?
C4 C3 N1 C1 -3.2(2) . . . . ?
C1 C2 N2 C4 -4.9(2) . . . . ?
C15 C2 N2 C4 172.54(14) . . . . ?
N4 C4 N2 C2 -178.01(14) . . . . ?
C3 C4 N2 C2 -0.7(2) . . . . ?
C6 C5 N3 C3 -0.6(2) . . . . ?
C7 C5 N3 C3 178.18(15) . . . . ?
N1 C3 N3 C5 178.97(14) . . . . ?
C4 C3 N3 C5 -0.5(2) . . . . ?
C5 C6 N4 C4 0.6(2) . . . . ?
C8 C6 N4 C4 -178.96(15) . . . . ?
N2 C4 N4 C6 175.65(14) . . . . ?
C3 C4 N4 C6 -1.7(2) . . . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_kn241211c_1_a
_database_code_depnum_ccdc_archive 'CCDC 2419630'
loop_
_audit_author_name
_audit_author_address
'Akiko Hori'
;Shibaura Institute of Technology
Japan
;
_audit_update_record             
;
2025-01-25 deposited with the CCDC.	2025-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H10 N6, C10 H8'
_chemical_formula_sum            'C30 H18 N6'
_chemical_formula_weight         462.50

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.312(6)
_cell_length_b                   7.042(4)
_cell_length_c                   26.902(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.740(17)
_cell_angle_gamma                90
_cell_volume                     2306(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    160
_cell_measurement_reflns_used    5255
_cell_measurement_theta_min      2.4346
_cell_measurement_theta_max      26.3600

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.285
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.161
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Goniometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            22427
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.435
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_full        25.024
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4065
_reflns_number_gt                2993
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebshle, rev 924)'
_computing_publication_material  ?
_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)+(0.0334P)²+2.0311P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0122(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4065
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0647
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
C1 C 0.34793(19) 0.5681(3) 0.62748(9) 0.0323(6) Uani 1 1 d . . . . .
C2 C 0.2492(2) 0.4579(4) 0.62998(9) 0.0332(6) Uani 1 1 d . . . . .
C3 C 0.39055(19) 0.5499(4) 0.71297(9) 0.0325(6) Uani 1 1 d . . . . .
C4 C 0.2897(2) 0.4597(3) 0.71581(9) 0.0326(6) Uani 1 1 d . . . . .
C5 C 0.4317(2) 0.5417(4) 0.79788(9) 0.0353(6) Uani 1 1 d . . . . .
C6 C 0.3295(2) 0.4550(4) 0.80080(9) 0.0348(6) Uani 1 1 d . . . . .
C7 C 0.5048(2) 0.5895(4) 0.84353(10) 0.0413(7) Uani 1 1 d . . . . .
C8 C 0.2979(2) 0.4124(4) 0.84921(10) 0.0425(7) Uani 1 1 d . . . . .
C9 C 0.3756(2) 0.6452(4) 0.57950(9) 0.0356(6) Uani 1 1 d . . . . .
C10 C 0.2965(2) 0.7270(4) 0.54338(10) 0.0456(7) Uani 1 1 d . . . . .
H10 H 0.222109 0.731851 0.548839 0.055 Uiso 1 1 calc R U . . .
C11 C 0.3252(3) 0.8009(4) 0.49970(10) 0.0541(8) Uani 1 1 d . . . . .
H11 H 0.270764 0.856975 0.475286 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4330(3) 0.7934(4) 0.49155(11) 0.0565(9) Uani 1 1 d . . . . .
H12 H 0.452530 0.841513 0.461131 0.068 Uiso 1 1 calc R U . . .
C13 C 0.5117(3) 0.7168(5) 0.52719(11) 0.0587(9) Uani 1 1 d . . . . .
H13 H 0.586016 0.713996 0.521634 0.070 Uiso 1 1 calc R U . . .
C14 C 0.4840(2) 0.6433(4) 0.57136(10) 0.0439(7) Uani 1 1 d . . . . .
H14 H 0.539405 0.591448 0.596072 0.053 Uiso 1 1 calc R U . . .
C15 C 0.1756(2) 0.3850(4) 0.58511(9) 0.0353(6) Uani 1 1 d . . . . .
C16 C 0.0633(2) 0.3849(4) 0.58551(10) 0.0409(7) Uani 1 1 d . . . . .
H16 H 0.034716 0.433878 0.613766 0.049 Uiso 1 1 calc R U . . .
C17 C -0.0071(2) 0.3138(4) 0.54504(11) 0.0520(8) Uani 1 1 d . . . . .
H17 H -0.084261 0.317234 0.545066 0.062 Uiso 1 1 calc R U . . .
C18 C 0.0344(3) 0.2374(4) 0.50434(11) 0.0535(8) Uani 1 1 d . . . . .
H18 H -0.014276 0.187299 0.476650 0.064 Uiso 1 1 calc R U . . .
C19 C 0.1460(3) 0.2340(4) 0.50402(10) 0.0512(8) Uani 1 1 d . . . . .
H19 H 0.174445 0.181500 0.476119 0.061 Uiso 1 1 calc R U . . .
C20 C 0.2169(2) 0.3072(4) 0.54435(10) 0.0433(7) Uani 1 1 d . . . . .
H20 H 0.293987 0.304217 0.544160 0.052 Uiso 1 1 calc R U . . .
C21 C 0.2468(4) 0.8908(6) 0.8239(2) 0.0887(14) Uani 1 1 d . . . . .
H21 H 0.301554 0.916050 0.851993 0.106 Uiso 1 1 calc R U . . .
C22 C 0.2662(3) 0.9343(5) 0.7760(2) 0.0865(14) Uani 1 1 d . . . . .
H22 H 0.334702 0.988345 0.771359 0.104 Uiso 1 1 calc R U . . .
C23 C 0.1855(3) 0.8996(4) 0.73374(16) 0.0611(9) Uani 1 1 d . . . . .
C24 C 0.1993(4) 0.9429(5) 0.6827(2) 0.0852(14) Uani 1 1 d . . . . .
H24 H 0.266656 0.995163 0.675981 0.102 Uiso 1 1 calc R U . . .
C25 C 0.1169(5) 0.9096(6) 0.64425(19) 0.0936(14) Uani 1 1 d . . . . .
H25 H 0.126589 0.941358 0.610890 0.112 Uiso 1 1 calc R U . . .
C26 C 0.0204(4) 0.8313(5) 0.65276(16) 0.0807(12) Uani 1 1 d . . . . .
H26 H -0.036123 0.808499 0.625208 0.097 Uiso 1 1 calc R U . . .
C27 C 0.0036(3) 0.7853(4) 0.69987(14) 0.0609(9) Uani 1 1 d . . . . .
H27 H -0.064172 0.729259 0.704772 0.073 Uiso 1 1 calc R U . . .
C28 C 0.0853(2) 0.8194(4) 0.74193(12) 0.0482(7) Uani 1 1 d . . . . .
C29 C 0.0686(3) 0.7763(4) 0.79148(13) 0.0587(9) Uani 1 1 d . . . . .
H29 H 0.000695 0.722444 0.796994 0.070 Uiso 1 1 calc R U . . .
C30 C 0.1472(3) 0.8100(5) 0.83105(15) 0.0756(11) Uani 1 1 d . . . . .
H30 H 0.134609 0.778405 0.864029 0.091 Uiso 1 1 calc R U . . .
N1 N 0.41798(16) 0.6077(3) 0.66821(7) 0.0358(5) Uani 1 1 d . . . . .
N2 N 0.22056(17) 0.4103(3) 0.67359(7) 0.0345(5) Uani 1 1 d . . . . .
N3 N 0.46331(16) 0.5905(3) 0.75465(8) 0.0364(5) Uani 1 1 d . . . . .
N4 N 0.25834(17) 0.4118(3) 0.76043(8) 0.0366(5) Uani 1 1 d . . . . .
N5 N 0.5610(2) 0.6331(4) 0.87946(9) 0.0584(7) Uani 1 1 d . . . . .
N6 N 0.2739(2) 0.3829(4) 0.88782(9) 0.0599(7) Uani 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
C1 N1 1.317(3) . ?
C1 C2 1.452(3) . ?
C1 C9 1.487(3) . ?
C2 N2 1.319(3) . ?
C2 C15 1.487(3) . ?
C3 N3 1.355(3) . ?
C3 N1 1.361(3) . ?
C3 C4 1.407(3) . ?
C4 N2 1.357(3) . ?
C4 N4 1.358(3) . ?
C5 N3 1.327(3) . ?
C5 C6 1.411(4) . ?
C5 C7 1.448(4) . ?
C6 N4 1.323(3) . ?
C6 C8 1.446(4) . ?
C7 N5 1.142(3) . ?
C8 N6 1.141(3) . ?
C9 C14 1.385(4) . ?
C9 C10 1.392(4) . ?
C10 C11 1.379(4) . ?
C11 C12 1.379(4) . ?
C12 C13 1.366(4) . ?
C13 C14 1.385(4) . ?
C15 C16 1.384(4) . ?
C15 C20 1.390(4) . ?
C16 C17 1.379(4) . ?
C17 C18 1.385(4) . ?
C18 C19 1.376(4) . ?
C19 C20 1.385(4) . ?
C21 C22 1.380(6) . ?
C21 C30 1.392(6) . ?
C22 C23 1.413(5) . ?
C23 C28 1.405(4) . ?
C23 C24 1.441(5) . ?
C24 C25 1.355(6) . ?
C25 C26 1.360(6) . ?
C26 C27 1.354(5) . ?
C27 C28 1.416(4) . ?
C28 C29 1.412(4) . ?
C29 C30 1.346(5) . ?

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
N1 C1 C2 121.4(2) . . ?
N1 C1 C9 115.9(2) . . ?
C2 C1 C9 122.6(2) . . ?
N2 C2 C1 121.1(2) . . ?
N2 C2 C15 114.9(2) . . ?
C1 C2 C15 123.9(2) . . ?
N3 C3 N1 116.6(2) . . ?
N3 C3 C4 121.9(2) . . ?
N1 C3 C4 121.5(2) . . ?
N2 C4 N4 116.7(2) . . ?
N2 C4 C3 121.1(2) . . ?
N4 C4 C3 122.1(2) . . ?
N3 C5 C6 122.9(2) . . ?
N3 C5 C7 117.1(2) . . ?
C6 C5 C7 119.9(2) . . ?
N4 C6 C5 122.6(2) . . ?
N4 C6 C8 117.2(2) . . ?
C5 C6 C8 120.3(2) . . ?
N5 C7 C5 177.8(3) . . ?
N6 C8 C6 178.4(3) . . ?
C14 C9 C10 118.9(2) . . ?
C14 C9 C1 119.1(2) . . ?
C10 C9 C1 121.9(2) . . ?
C11 C10 C9 120.6(3) . . ?
C12 C11 C10 119.9(3) . . ?
C13 C12 C11 120.0(3) . . ?
C12 C13 C14 120.6(3) . . ?
C9 C14 C13 120.0(3) . . ?
C16 C15 C20 119.4(2) . . ?
C16 C15 C2 118.7(2) . . ?
C20 C15 C2 121.7(2) . . ?
C17 C16 C15 120.2(3) . . ?
C16 C17 C18 120.1(3) . . ?
C19 C18 C17 120.0(3) . . ?
C18 C19 C20 120.0(3) . . ?
C19 C20 C15 120.2(3) . . ?
C22 C21 C30 120.1(4) . . ?
C21 C22 C23 120.8(4) . . ?
C28 C23 C22 118.1(4) . . ?
C28 C23 C24 117.9(4) . . ?
C22 C23 C24 124.0(4) . . ?
C25 C24 C23 120.5(4) . . ?
C24 C25 C26 120.9(4) . . ?
C27 C26 C25 121.1(4) . . ?
C26 C27 C28 121.1(4) . . ?
C23 C28 C29 119.4(3) . . ?
C23 C28 C27 118.5(3) . . ?
C29 C28 C27 122.0(3) . . ?
C30 C29 C28 121.2(3) . . ?
C29 C30 C21 120.3(4) . . ?
C1 N1 C3 117.0(2) . . ?
C2 N2 C4 117.4(2) . . ?
C5 N3 C3 115.2(2) . . ?
C6 N4 C4 115.3(2) . . ?

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 C1 C2 N2 7.1(4) . . . . ?
C9 C1 C2 N2 -172.0(2) . . . . ?
N1 C1 C2 C15 -170.8(2) . . . . ?
C9 C1 C2 C15 10.0(4) . . . . ?
N3 C3 C4 N2 -176.2(2) . . . . ?
N1 C3 C4 N2 6.5(4) . . . . ?
N3 C3 C4 N4 1.5(4) . . . . ?
N1 C3 C4 N4 -175.9(2) . . . . ?
N3 C5 C6 N4 1.6(4) . . . . ?
C7 C5 C6 N4 178.5(2) . . . . ?
N3 C5 C6 C8 -177.4(2) . . . . ?
C7 C5 C6 C8 -0.5(4) . . . . ?
N1 C1 C9 C14 39.7(3) . . . . ?
C2 C1 C9 C14 -141.1(3) . . . . ?
N1 C1 C9 C10 -137.5(3) . . . . ?
C2 C1 C9 C10 41.7(4) . . . . ?
C14 C9 C10 C11 1.4(4) . . . . ?
C1 C9 C10 C11 178.6(3) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C10 C11 C12 C13 -1.5(5) . . . . ?
C11 C12 C13 C14 1.1(5) . . . . ?
C10 C9 C14 C13 -1.9(4) . . . . ?
C1 C9 C14 C13 -179.1(3) . . . . ?
C12 C13 C14 C9 0.6(5) . . . . ?
N2 C2 C15 C16 39.6(3) . . . . ?
C1 C2 C15 C16 -142.4(3) . . . . ?
N2 C2 C15 C20 -136.5(3) . . . . ?
C1 C2 C15 C20 41.5(4) . . . . ?
C20 C15 C16 C17 -2.2(4) . . . . ?
C2 C15 C16 C17 -178.3(2) . . . . ?
C15 C16 C17 C18 1.8(4) . . . . ?
C16 C17 C18 C19 -0.7(5) . . . . ?
C17 C18 C19 C20 -0.1(5) . . . . ?
C18 C19 C20 C15 -0.3(4) . . . . ?
C16 C15 C20 C19 1.4(4) . . . . ?
C2 C15 C20 C19 177.5(3) . . . . ?
C30 C21 C22 C23 0.6(5) . . . . ?
C21 C22 C23 C28 -0.1(5) . . . . ?
C21 C22 C23 C24 179.3(3) . . . . ?
C28 C23 C24 C25 1.1(5) . . . . ?
C22 C23 C24 C25 -178.4(3) . . . . ?
C23 C24 C25 C26 -1.3(6) . . . . ?
C24 C25 C26 C27 0.4(6) . . . . ?
C25 C26 C27 C28 0.8(5) . . . . ?
C22 C23 C28 C29 -0.1(4) . . . . ?
C24 C23 C28 C29 -179.6(3) . . . . ?
C22 C23 C28 C27 179.5(3) . . . . ?
C24 C23 C28 C27 0.1(4) . . . . ?
C26 C27 C28 C23 -1.0(4) . . . . ?
C26 C27 C28 C29 178.7(3) . . . . ?
C23 C28 C29 C30 -0.2(4) . . . . ?
C27 C28 C29 C30 -179.9(3) . . . . ?
C28 C29 C30 C21 0.8(5) . . . . ?
C22 C21 C30 C29 -1.0(5) . . . . ?
C2 C1 N1 C3 -3.6(3) . . . . ?
C9 C1 N1 C3 175.6(2) . . . . ?
N3 C3 N1 C1 179.7(2) . . . . ?
C4 C3 N1 C1 -2.8(3) . . . . ?
C1 C2 N2 C4 -3.4(3) . . . . ?
C15 C2 N2 C4 174.7(2) . . . . ?
N4 C4 N2 C2 179.2(2) . . . . ?
C3 C4 N2 C2 -3.0(3) . . . . ?
C6 C5 N3 C3 -0.5(4) . . . . ?
C7 C5 N3 C3 -177.5(2) . . . . ?
N1 C3 N3 C5 176.5(2) . . . . ?
C4 C3 N3 C5 -0.9(3) . . . . ?
C5 C6 N4 C4 -1.1(4) . . . . ?
C8 C6 N4 C4 178.0(2) . . . . ?
N2 C4 N4 C6 177.4(2) . . . . ?
C3 C4 N4 C6 -0.4(3) . . . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.044

