# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_CSJ06_86_1_a
_database_code_depnum_ccdc_archive 'CCDC 2101334'
loop_
_audit_author_name
_audit_author_address
'wenlong Liu'
;Yangzhou University
China
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N4'
_chemical_formula_sum            'C19 H16 N4'
_chemical_formula_weight         300.36

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.3310(9)
_cell_length_b                   9.7410(13)
_cell_length_c                   13.1586(19)
_cell_angle_alpha                80.485(4)
_cell_angle_beta                 88.980(5)
_cell_angle_gamma                82.009(5)
_cell_volume                     792.55(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3615
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.13

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6905
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source.type              microfocus
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10488
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.437
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             2766
_reflns_number_gt                1791
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0631P)²+0.1625P] 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         2766
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1374
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 -0.3080(4) 0.7084(3) 0.5161(2) 0.0826(8) Uani 1 1 d . . . . .
H1 H -0.419913 0.701690 0.562555 0.099 Uiso 1 1 calc R U . . .
C2 C -0.2761(4) 0.6215(3) 0.4451(2) 0.0935(9) Uani 1 1 d . . . . .
H2 H -0.364566 0.553217 0.443607 0.112 Uiso 1 1 calc R U . . .
C3 C -0.1127(4) 0.6343(3) 0.37498(19) 0.0841(8) Uani 1 1 d . . . . .
H3 H -0.092998 0.574166 0.326585 0.101 Uiso 1 1 calc R U . . .
C4 C 0.0212(3) 0.7331(2) 0.37469(16) 0.0522(5) Uani 1 1 d . . . . .
C5 C -0.0120(4) 0.8168(2) 0.4486(2) 0.0813(8) Uani 1 1 d . . . . .
H5 H 0.077967 0.883793 0.451716 0.098 Uiso 1 1 calc R U . . .
C6 C -0.1749(5) 0.8049(3) 0.5184(2) 0.1009(10) Uani 1 1 d . . . . .
H6 H -0.193780 0.863662 0.567775 0.121 Uiso 1 1 calc R U . . .
C7 C 0.1968(3) 0.7533(2) 0.29675(18) 0.0629(6) Uani 1 1 d . . . . .
H7A H 0.141251 0.824713 0.239616 0.076 Uiso 1 1 calc R U . . .
H7B H 0.310767 0.788612 0.328520 0.076 Uiso 1 1 calc R U . . .
C8 C 0.2890(3) 0.6241(2) 0.25497(17) 0.0567(6) Uani 1 1 d . . . . .
H8A H 0.179236 0.594766 0.216210 0.068 Uiso 1 1 calc R U . . .
H8B H 0.330659 0.549288 0.312242 0.068 Uiso 1 1 calc R U . . .
C9 C 0.4799(3) 0.64329(19) 0.18620(15) 0.0470(5) Uani 1 1 d . . . . .
C10 C 0.6131(3) 0.53015(19) 0.15592(14) 0.0440(5) Uani 1 1 d . . . . .
C11 C 0.5835(3) 0.3812(2) 0.19224(15) 0.0464(5) Uani 1 1 d . . . . .
C12 C 0.3968(4) 0.3297(2) 0.17371(17) 0.0600(6) Uani 1 1 d . . . . .
H12 H 0.284741 0.389534 0.138478 0.072 Uiso 1 1 calc R U . . .
C13 C 0.3761(4) 0.1905(3) 0.2072(2) 0.0716(7) Uani 1 1 d . . . . .
H13 H 0.252534 0.155836 0.192369 0.086 Uiso 1 1 calc R U . . .
C14 C 0.5371(5) 0.1035(3) 0.2620(2) 0.0780(8) Uani 1 1 d . . . . .
H14 H 0.521120 0.010287 0.286120 0.094 Uiso 1 1 calc R U . . .
C15 C 0.7222(4) 0.1527(2) 0.2818(2) 0.0781(7) Uani 1 1 d . . . . .
H15 H 0.831648 0.092975 0.319131 0.094 Uiso 1 1 calc R U . . .
C16 C 0.7456(4) 0.2909(2) 0.24624(18) 0.0632(6) Uani 1 1 d . . . . .
H16 H 0.872278 0.323590 0.258779 0.076 Uiso 1 1 calc R U . . .
C17 C 0.8294(3) 0.68000(19) 0.06696(14) 0.0457(5) Uani 1 1 d . . . . .
C18 C 0.6946(3) 0.79116(19) 0.09831(15) 0.0508(5) Uani 1 1 d . . . . .
C19 C 0.7376(3) 0.9330(2) 0.06796(19) 0.0645(7) Uani 1 1 d . . . . .
N1 N 0.5240(3) 0.77288(16) 0.15742(13) 0.0549(5) Uani 1 1 d . . . . .
N2 N 0.7845(2) 0.54851(15) 0.09660(12) 0.0459(4) Uani 1 1 d . . . . .
N3 N 0.7781(4) 1.0432(2) 0.04223(19) 0.0905(8) Uani 1 1 d . . . . .
N4 N 1.0027(3) 0.69723(17) 0.00882(13) 0.0586(5) Uani 1 1 d . . . . .
H4A H 1.081130 0.625357 -0.008367 0.070 Uiso 1 1 calc R U . . .
H4B H 1.035433 0.780159 -0.011316 0.070 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
C1 C6 1.350(4) . ?
C1 C2 1.356(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(3) . ?
C4 C7 1.510(3) . ?
C5 C6 1.374(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.497(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.511(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.323(2) . ?
C9 C10 1.400(3) . ?
C10 N2 1.340(2) . ?
C10 C11 1.487(2) . ?
C11 C16 1.379(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N4 1.340(2) . ?
C17 N2 1.344(2) . ?
C17 C18 1.396(3) . ?
C18 N1 1.335(2) . ?
C18 C19 1.436(3) . ?
C19 N3 1.133(2) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?

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
C6 C1 C2 119.1(2) . . ?
C6 C1 H1 120.4 . . ?
C2 C1 H1 120.4 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 116.72(19) . . ?
C5 C4 C7 120.12(19) . . ?
C3 C4 C7 123.1(2) . . ?
C4 C5 C6 121.7(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 120.5(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C4 115.15(17) . . ?
C8 C7 H7A 108.5 . . ?
C4 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C4 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 114.06(16) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N1 C9 C10 119.85(16) . . ?
N1 C9 C8 117.45(17) . . ?
C10 C9 C8 122.65(16) . . ?
N2 C10 C9 122.01(16) . . ?
N2 C10 C11 115.13(16) . . ?
C9 C10 C11 122.75(16) . . ?
C16 C11 C12 118.59(19) . . ?
C16 C11 C10 119.38(17) . . ?
C12 C11 C10 122.03(19) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 119.8(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
N4 C17 N2 117.91(17) . . ?
N4 C17 C18 123.42(16) . . ?
N2 C17 C18 118.67(16) . . ?
N1 C18 C17 123.03(16) . . ?
N1 C18 C19 116.80(17) . . ?
C17 C18 C19 120.17(17) . . ?
N3 C19 C18 177.5(2) . . ?
C9 N1 C18 118.12(16) . . ?
C10 N2 C17 118.31(16) . . ?
C17 N4 H4A 120.0 . . ?
C17 N4 H4B 120.0 . . ?
H4A N4 H4B 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
C6 C1 C2 C3 -1.5(5) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C2 C3 C4 C7 -177.8(2) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C7 C4 C5 C6 177.6(3) . . . . ?
C2 C1 C6 C5 1.3(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C5 C4 C7 C8 151.8(2) . . . . ?
C3 C4 C7 C8 -29.2(3) . . . . ?
C4 C7 C8 C9 -173.66(18) . . . . ?
C7 C8 C9 N1 -10.3(3) . . . . ?
C7 C8 C9 C10 167.3(2) . . . . ?
N1 C9 C10 N2 -1.1(3) . . . . ?
C8 C9 C10 N2 -178.61(18) . . . . ?
N1 C9 C10 C11 174.96(18) . . . . ?
C8 C9 C10 C11 -2.6(3) . . . . ?
N2 C10 C11 C16 56.1(2) . . . . ?
C9 C10 C11 C16 -120.2(2) . . . . ?
N2 C10 C11 C12 -124.1(2) . . . . ?
C9 C10 C11 C12 59.7(3) . . . . ?
C16 C11 C12 C13 -1.1(3) . . . . ?
C10 C11 C12 C13 179.00(18) . . . . ?
C11 C12 C13 C14 2.3(3) . . . . ?
C12 C13 C14 C15 -1.8(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C11 1.1(4) . . . . ?
C12 C11 C16 C15 -0.5(3) . . . . ?
C10 C11 C16 C15 179.3(2) . . . . ?
N4 C17 C18 N1 -179.04(19) . . . . ?
N2 C17 C18 N1 0.7(3) . . . . ?
N4 C17 C18 C19 0.3(3) . . . . ?
N2 C17 C18 C19 -179.92(19) . . . . ?
C10 C9 N1 C18 1.1(3) . . . . ?
C8 C9 N1 C18 178.71(18) . . . . ?
C17 C18 N1 C9 -0.9(3) . . . . ?
C19 C18 N1 C9 179.71(19) . . . . ?
C9 C10 N2 C17 0.9(3) . . . . ?
C11 C10 N2 C17 -175.45(16) . . . . ?
N4 C17 N2 C10 179.11(17) . . . . ?
C18 C17 N2 C10 -0.7(3) . . . . ?

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
N4 H4B N3 0.86 2.20 3.025(2) 161.0 2_775 yes
N4 H4A N2 0.86 2.27 3.099(2) 161.8 2_765 yes

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.033



