# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ArS_564c
_database_code_depnum_ccdc_archive 'CCDC 1988182'
loop_
_audit_author_name
_audit_author_address
'Anatoly Mishnev'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2020-03-04 deposited with the CCDC.	2021-03-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H14 N6'
_chemical_formula_weight         386.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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                   9.09690(10)
_cell_length_b                   22.5058(2)
_cell_length_c                   9.14900(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.6630(10)
_cell_angle_gamma                90
_cell_volume                     1803.55(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    12802
_cell_measurement_theta_min      3.9220
_cell_measurement_theta_max      75.9630

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.711
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17262
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.928
_diffrn_reflns_theta_max         76.369
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3686
_reflns_number_gt                3423
_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       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_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)+(0.0499P)²+0.5293P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3686
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.46314(10) 0.36048(4) -0.02239(10) 0.0248(2) Uani 1 1 d . . . . .
N16 N 0.74254(11) 0.35026(4) 0.60295(11) 0.0267(2) Uani 1 1 d . . . . .
N18 N 0.80684(11) 0.32676(4) 0.85289(11) 0.0282(2) Uani 1 1 d . . . . .
N23 N 0.90375(12) 0.43762(4) 0.61419(11) 0.0287(2) Uani 1 1 d . . . . .
N21 N 1.05427(12) 0.45945(4) 0.86911(11) 0.0295(2) Uani 1 1 d . . . . .
N26 N 1.07581(12) 0.39289(5) 1.21368(12) 0.0329(2) Uani 1 1 d . . . . .
C2 C 0.49615(12) 0.40876(5) -0.10564(12) 0.0239(2) Uani 1 1 d . . . . .
C9 C 0.33753(12) 0.33023(5) -0.11337(12) 0.0229(2) Uani 1 1 d . . . . .
C7 C 0.39081(13) 0.40903(5) -0.24985(12) 0.0243(2) Uani 1 1 d . . . . .
C8 C 0.29098(12) 0.35855(5) -0.25586(12) 0.0234(2) Uani 1 1 d . . . . .
C13 C 0.53248(13) 0.35084(5) 0.13438(12) 0.0238(2) Uani 1 1 d . . . . .
C20 C 0.99294(13) 0.41313(5) 0.92392(13) 0.0257(2) Uani 1 1 d . . . . .
C19 C 0.88625(12) 0.37649(5) 0.82893(12) 0.0249(2) Uani 1 1 d . . . . .
C27 C 0.26400(13) 0.27963(5) -0.08170(13) 0.0259(2) Uani 1 1 d . . . . .
H27 H 0.295099 0.261019 0.012382 0.031 Uiso 1 1 calc R U . . .
C30 C 0.16883(13) 0.33562(5) -0.36879(12) 0.0259(2) Uani 1 1 d . . . . .
H30 H 0.137513 0.353853 -0.463351 0.031 Uiso 1 1 calc R U . . .
C24 C 0.84821(13) 0.39203(5) 0.67455(12) 0.0247(2) Uani 1 1 d . . . . .
C25 C 1.04075(13) 0.40256(5) 1.08617(13) 0.0268(2) Uani 1 1 d . . . . .
C10 C 0.67075(13) 0.34675(5) 0.44349(13) 0.0255(2) Uani 1 1 d . . . . .
C15 C 0.76027(13) 0.35204(5) 0.34275(13) 0.0279(2) Uani 1 1 d . . . . .
H15 H 0.865911 0.354709 0.378894 0.033 Uiso 1 1 calc R U . . .
C28 C 0.14242(13) 0.25791(5) -0.19573(13) 0.0274(2) Uani 1 1 d . . . . .
H28 H 0.091154 0.224211 -0.177050 0.033 Uiso 1 1 calc R U . . .
C14 C 0.69098(13) 0.35330(5) 0.18825(13) 0.0268(2) Uani 1 1 d . . . . .
H14 H 0.750389 0.355790 0.120171 0.032 Uiso 1 1 calc R U . . .
C29 C 0.09502(13) 0.28527(5) -0.33768(13) 0.0276(2) Uani 1 1 d . . . . .
H29 H 0.013351 0.269579 -0.411858 0.033 Uiso 1 1 calc R U . . .
C12 C 0.44451(13) 0.34218(5) 0.23576(13) 0.0259(2) Uani 1 1 d . . . . .
H12 H 0.339274 0.337740 0.199607 0.031 Uiso 1 1 calc R U . . .
C3 C 0.60673(13) 0.45292(5) -0.06219(13) 0.0282(2) Uani 1 1 d . . . . .
H3 H 0.676748 0.452525 0.033014 0.034 Uiso 1 1 calc R U . . .
C11 C 0.51383(13) 0.34017(5) 0.39087(13) 0.0266(2) Uani 1 1 d . . . . .
H11 H 0.455371 0.334445 0.458861 0.032 Uiso 1 1 calc R U . . .
C17 C 0.72371(13) 0.31312(5) 0.71651(13) 0.0286(2) Uani 1 1 d . . . . .
H17 H 0.657175 0.280919 0.697642 0.034 Uiso 1 1 calc R U . . .
C22 C 1.00644(14) 0.46876(5) 0.71883(13) 0.0301(3) Uani 1 1 d . . . . .
H22 H 1.050170 0.500966 0.682578 0.036 Uiso 1 1 calc R U . . .
C6 C 0.39347(15) 0.45487(5) -0.35209(13) 0.0308(3) Uani 1 1 d . . . . .
H6 H 0.323234 0.455827 -0.447141 0.037 Uiso 1 1 calc R U . . .
C4 C 0.60830(14) 0.49740(5) -0.16625(15) 0.0317(3) Uani 1 1 d . . . . .
H4 H 0.681607 0.527187 -0.140489 0.038 Uiso 1 1 calc R U . . .
C5 C 0.50275(16) 0.49871(5) -0.30880(14) 0.0344(3) Uani 1 1 d . . . . .
H5 H 0.506078 0.529535 -0.375530 0.041 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 C9 1.3959(14) . ?
N1 C2 1.4053(14) . ?
N1 C13 1.4190(14) . ?
N16 C24 1.3773(15) . ?
N16 C17 1.3797(15) . ?
N16 C10 1.4306(14) . ?
N18 C17 1.3090(15) . ?
N18 C19 1.3813(15) . ?
N23 C24 1.3281(15) . ?
N23 C22 1.3406(16) . ?
N21 C22 1.3419(15) . ?
N21 C20 1.3419(15) . ?
N26 C25 1.1441(15) . ?
C2 C3 1.3934(16) . ?
C2 C7 1.4059(15) . ?
C9 C27 1.3903(15) . ?
C9 C8 1.4096(15) . ?
C7 C6 1.3971(16) . ?
C7 C8 1.4462(15) . ?
C8 C30 1.3959(15) . ?
C13 C12 1.3927(16) . ?
C13 C14 1.3933(16) . ?
C20 C19 1.3863(16) . ?
C20 C25 1.4494(16) . ?
C19 C24 1.4047(15) . ?
C27 C28 1.3883(16) . ?
C27 H27 0.9300 . ?
C30 C29 1.3855(16) . ?
C30 H30 0.9300 . ?
C10 C11 1.3858(16) . ?
C10 C15 1.3900(16) . ?
C15 C14 1.3839(16) . ?
C15 H15 0.9300 . ?
C28 C29 1.3962(16) . ?
C28 H28 0.9300 . ?
C14 H14 0.9300 . ?
C29 H29 0.9300 . ?
C12 C11 1.3894(16) . ?
C12 H12 0.9300 . ?
C3 C4 1.3841(17) . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C17 H17 0.9300 . ?
C22 H22 0.9300 . ?
C6 C5 1.3806(18) . ?
C6 H6 0.9300 . ?
C4 C5 1.3955(18) . ?
C4 H4 0.9300 . ?
C5 H5 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
C9 N1 C2 108.32(9) . . ?
C9 N1 C13 126.67(9) . . ?
C2 N1 C13 124.36(9) . . ?
C24 N16 C17 105.54(9) . . ?
C24 N16 C10 126.20(9) . . ?
C17 N16 C10 128.26(10) . . ?
C17 N18 C19 103.36(9) . . ?
C24 N23 C22 112.14(10) . . ?
C22 N21 C20 116.85(10) . . ?
C3 C2 N1 129.82(10) . . ?
C3 C2 C7 121.42(10) . . ?
N1 C2 C7 108.71(9) . . ?
C27 C9 N1 129.62(10) . . ?
C27 C9 C8 121.45(10) . . ?
N1 C9 C8 108.91(9) . . ?
C6 C7 C2 120.06(11) . . ?
C6 C7 C8 132.75(11) . . ?
C2 C7 C8 107.11(9) . . ?
C30 C8 C9 119.85(10) . . ?
C30 C8 C7 133.22(10) . . ?
C9 C8 C7 106.94(9) . . ?
C12 C13 C14 119.72(10) . . ?
C12 C13 N1 121.07(10) . . ?
C14 C13 N1 119.12(10) . . ?
N21 C20 C19 121.28(10) . . ?
N21 C20 C25 118.04(10) . . ?
C19 C20 C25 120.67(10) . . ?
N18 C19 C20 133.64(10) . . ?
N18 C19 C24 111.34(10) . . ?
C20 C19 C24 115.02(10) . . ?
C28 C27 C9 117.54(10) . . ?
C28 C27 H27 121.2 . . ?
C9 C27 H27 121.2 . . ?
C29 C30 C8 118.91(10) . . ?
C29 C30 H30 120.5 . . ?
C8 C30 H30 120.5 . . ?
N23 C24 N16 128.65(10) . . ?
N23 C24 C19 126.33(11) . . ?
N16 C24 C19 105.02(10) . . ?
N26 C25 C20 178.09(13) . . ?
C11 C10 C15 120.78(10) . . ?
C11 C10 N16 120.26(10) . . ?
C15 C10 N16 118.92(10) . . ?
C14 C15 C10 119.49(10) . . ?
C14 C15 H15 120.3 . . ?
C10 C15 H15 120.3 . . ?
C27 C28 C29 121.81(11) . . ?
C27 C28 H28 119.1 . . ?
C29 C28 H28 119.1 . . ?
C15 C14 C13 120.20(10) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C30 C29 C28 120.44(10) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C11 C12 C13 120.06(10) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C4 C3 C2 117.40(11) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C10 C11 C12 119.49(10) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
N18 C17 N16 114.75(10) . . ?
N18 C17 H17 122.6 . . ?
N16 C17 H17 122.6 . . ?
N23 C22 N21 128.37(11) . . ?
N23 C22 H22 115.8 . . ?
N21 C22 H22 115.8 . . ?
C5 C6 C7 118.48(11) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C3 C4 C5 121.73(11) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 120.89(11) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.045

