# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2082645'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2021-05-10 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT198_shelx               
;
PROBLEM: Missing _diffrn_ambient_temperature   Datum ....     Please Add   
RESPONSE: ...
;
_vrf_PLAT097_shelx               
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.84 eA-3  
RESPONSE: There are two relatively large residual electron
denisty peaks at the extension of the C12-N3 bond.
The 0.84 eA-3 peak is located 1.10 ang from the N3 atom
and the next peak [0.80 eA-3] is located 1.11 ang from atom C12. After these, the next peaks fall off in density, 
0.50, 0.32 eA-3, etc. It is likely these residuals reflect
unresolved disorder in the fused nine-membered ring residue
where two co-planar, coincident residues of opposite
orientation are superimposed so, the 0.84 and 0.80 eA-3
peaks correspond to the positions of the putative N2' and
N4' atoms of the minor disorder component. Despite this
feature of the model, the chemical connectivity has been determined unambiguously.
;
_vrf_PLAT230_shelx               
;
PROBLEM: Hirshfeld Test Diff for    C12      --C14      .        8.0 s.u.  
RESPONSE: Based on the spectroscopic analysis and 
analytical data, the assignment of atoms is unambiguous,
with the alert likely arising as a result of disorder in
this region of the molecule.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N4'
_chemical_formula_sum            'C20 H16 N4'
_chemical_formula_weight         312.37

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           11
_space_group_name_H-M_alt        'P 21/m'
_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.23710(10)
_cell_length_b                   6.86320(10)
_cell_length_c                   16.2164(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.4780(10)
_cell_angle_gamma                90
_cell_volume                     789.35(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6410
_cell_measurement_theta_min      5.5670
_cell_measurement_theta_max      76.1380

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.089
_exptl_absorpt_coefficient_mu    0.634
_shelx_estimated_absorpt_T_min   0.843
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.448
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_ambient_environment      N~2~
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_detector_type            AtlasS2
_diffrn_reflns_number            10920
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.568
_diffrn_reflns_theta_max         75.300
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1774
_reflns_number_gt                1622
_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 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.39.31a (Rigaku Oxford Diffraction, 2017)
;
_computing_structure_solution    'SHELXT 2014/5'
_computing_structure_refinement  SHELXL-2018/3
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_publication_material  SHELXL-2018/3
_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)+(0.1078P)²+0.4133P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1774
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.1978
_refine_ls_wR_factor_gt          0.1938
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.6340(3) 0.750000 0.15165(15) 0.0459(6) Uani 1 2 d S T P . .
N2 N 0.6309(3) 0.750000 0.44951(16) 0.0513(6) Uani 1 2 d S T P . .
N3 N 0.9207(3) 0.750000 0.39999(14) 0.0417(5) Uani 1 2 d S T P . .
N4 N 1.1088(3) 0.750000 0.42513(15) 0.0473(6) Uani 1 2 d S T P . .
C1 C 0.5394(4) 0.750000 0.21144(17) 0.0392(6) Uani 1 2 d S T P . .
C2 C 0.3253(4) 0.750000 0.18087(18) 0.0430(6) Uani 1 2 d S T P . .
C3 C 0.3192(4) 0.750000 0.08756(18) 0.0459(7) Uani 1 2 d S T P . .
C4 C 0.1692(5) 0.750000 0.0191(2) 0.0673(10) Uani 1 2 d S T P . .
H4 H 0.045112 0.750000 0.026627 0.081 Uiso 1 2 calc R U P . .
C5 C 0.2104(6) 0.750000 -0.0610(2) 0.0711(10) Uani 1 2 d S T P . .
H5 H 0.112094 0.750000 -0.107710 0.085 Uiso 1 2 calc R U P . .
C6 C 0.3939(6) 0.750000 -0.0727(2) 0.0669(10) Uani 1 2 d S T P . .
H6 H 0.416611 0.750000 -0.127153 0.080 Uiso 1 2 calc R U P . .
C7 C 0.5438(5) 0.750000 -0.0059(2) 0.0569(8) Uani 1 2 d S T P . .
H7 H 0.667576 0.750000 -0.013808 0.068 Uiso 1 2 calc R U P . .
C8 C 0.5020(4) 0.750000 0.07444(17) 0.0439(6) Uani 1 2 d S T P . .
C9 C 0.2319(3) 0.5655(4) 0.20744(16) 0.0605(6) Uani 1 1 d . . . . .
H9A H 0.293532 0.452371 0.190925 0.091 Uiso 1 1 calc R U . . .
H9B H 0.101073 0.563565 0.180590 0.091 Uiso 1 1 calc R U . . .
H9C H 0.242613 0.565384 0.267409 0.091 Uiso 1 1 calc R U . . .
C10 C 0.6373(4) 0.750000 0.30042(17) 0.0423(6) Uani 1 2 d S T P . .
C11 C 0.5427(4) 0.750000 0.37006(18) 0.0498(7) Uani 1 2 d S T P . .
H11 H 0.411560 0.750000 0.358604 0.060 Uiso 1 2 calc R U P . .
C12 C 0.8158(4) 0.750000 0.46298(18) 0.0421(6) Uani 1 2 d S T P . .
C13 C 0.8289(4) 0.750000 0.31794(17) 0.0448(6) Uani 1 2 d S T P . .
H13 H 0.896240 0.750000 0.274718 0.054 Uiso 1 2 calc R U P . .
C14 C 0.9548(4) 0.750000 0.53902(18) 0.0452(7) Uani 1 2 d S T P . .
C15 C 0.9510(5) 0.750000 0.62640(19) 0.0520(7) Uani 1 2 d S T P . .
H15 H 0.837709 0.750000 0.645196 0.062 Uiso 1 2 calc R U P . .
C16 C 1.1202(5) 0.750000 0.68156(19) 0.0566(8) Uani 1 2 d S T P . .
H16 H 1.122740 0.750000 0.739125 0.068 Uiso 1 2 calc R U P . .
C17 C 1.2913(5) 0.750000 0.65228(19) 0.0523(7) Uani 1 2 d S T P . .
H17 H 1.404087 0.750000 0.691546 0.063 Uiso 1 2 calc R U P . .
C18 C 1.2981(4) 0.750000 0.56932(19) 0.0506(7) Uani 1 2 d S T P . .
H18 H 1.412752 0.750000 0.551670 0.061 Uiso 1 2 calc R U P . .
C19 C 1.1268(4) 0.750000 0.51105(17) 0.0437(6) Uani 1 2 d S T P . .


_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 C1 1.294(4) . ?
N1 C8 1.416(3) . ?
N2 C12 1.312(4) . ?
N2 C11 1.319(4) . ?
N3 N4 1.341(3) . ?
N3 C13 1.364(4) . ?
N3 C12 1.389(3) . ?
N4 C19 1.373(3) . ?
C1 C10 1.475(4) . ?
C1 C2 1.530(3) . ?
C2 C3 1.505(4) . ?
C2 C9 1.537(3) . ?
C2 C9 1.537(3) 4_575 ?
C3 C8 1.381(4) . ?
C3 C4 1.390(4) . ?
C4 C5 1.389(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.394(4) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C13 1.359(4) . ?
C10 C11 1.432(4) . ?
C11 H11 0.9300 . ?
C12 C14 1.428(4) . ?
C13 H13 0.9300 . ?
C14 C19 1.407(4) . ?
C14 C15 1.423(4) . ?
C15 C16 1.365(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.412(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.356(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.401(4) . ?
C18 H18 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
C1 N1 C8 107.4(2) . . ?
C12 N2 C11 116.2(2) . . ?
N4 N3 C13 124.4(2) . . ?
N4 N3 C12 116.6(2) . . ?
C13 N3 C12 119.1(2) . . ?
N3 N4 C19 101.2(2) . . ?
N1 C1 C10 120.7(2) . . ?
N1 C1 C2 114.2(2) . . ?
C10 C1 C2 125.1(2) . . ?
C3 C2 C1 98.7(2) . . ?
C3 C2 C9 110.82(16) . . ?
C1 C2 C9 112.51(15) . . ?
C3 C2 C9 110.82(16) . 4_575 ?
C1 C2 C9 112.51(15) . 4_575 ?
C9 C2 C9 110.9(3) . 4_575 ?
C8 C3 C4 119.8(3) . . ?
C8 C3 C2 108.5(2) . . ?
C4 C3 C2 131.7(3) . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C7 C6 C5 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C6 C7 C8 116.9(3) . . ?
C6 C7 H7 121.5 . . ?
C8 C7 H7 121.5 . . ?
C3 C8 C7 122.4(3) . . ?
C3 C8 N1 111.2(2) . . ?
C7 C8 N1 126.3(3) . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C13 C10 C11 117.6(3) . . ?
C13 C10 C1 118.4(3) . . ?
C11 C10 C1 124.0(3) . . ?
N2 C11 C10 123.8(3) . . ?
N2 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
N2 C12 N3 124.5(3) . . ?
N2 C12 C14 131.6(2) . . ?
N3 C12 C14 103.9(2) . . ?
C10 C13 N3 118.9(3) . . ?
C10 C13 H13 120.6 . . ?
N3 C13 H13 120.6 . . ?
C19 C14 C15 121.0(3) . . ?
C19 C14 C12 103.8(2) . . ?
C15 C14 C12 135.2(3) . . ?
C16 C15 C14 117.4(3) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 122.8(3) . . ?
C18 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
C17 C18 C19 117.8(3) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 H18 121.1 . . ?
N4 C19 C18 125.2(3) . . ?
N4 C19 C14 114.6(3) . . ?
C18 C19 C14 120.2(3) . . ?

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
C13 N3 N4 C19 180.000(1) . . . . ?
C12 N3 N4 C19 0.000(1) . . . . ?
C8 N1 C1 C10 180.000(0) . . . . ?
C8 N1 C1 C2 0.000(0) . . . . ?
N1 C1 C2 C3 0.000(0) . . . . ?
C10 C1 C2 C3 180.000(0) . . . . ?
N1 C1 C2 C9 116.90(18) . . . . ?
C10 C1 C2 C9 -63.10(18) . . . . ?
N1 C1 C2 C9 -116.90(18) . . . 4_575 ?
C10 C1 C2 C9 63.10(18) . . . 4_575 ?
C1 C2 C3 C8 0.000(0) . . . . ?
C9 C2 C3 C8 -118.18(16) . . . . ?
C9 C2 C3 C8 118.18(16) 4_575 . . . ?
C1 C2 C3 C4 180.000(0) . . . . ?
C9 C2 C3 C4 61.82(16) . . . . ?
C9 C2 C3 C4 -61.82(16) 4_575 . . . ?
C8 C3 C4 C5 0.000(0) . . . . ?
C2 C3 C4 C5 180.000(0) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C4 C5 C6 C7 0.000(0) . . . . ?
C5 C6 C7 C8 0.000(0) . . . . ?
C4 C3 C8 C7 0.000(0) . . . . ?
C2 C3 C8 C7 180.000(0) . . . . ?
C4 C3 C8 N1 180.000(0) . . . . ?
C2 C3 C8 N1 0.000(0) . . . . ?
C6 C7 C8 C3 0.000(0) . . . . ?
C6 C7 C8 N1 180.000(0) . . . . ?
C1 N1 C8 C3 0.000(0) . . . . ?
C1 N1 C8 C7 180.000(0) . . . . ?
N1 C1 C10 C13 0.000(1) . . . . ?
C2 C1 C10 C13 180.000(0) . . . . ?
N1 C1 C10 C11 180.000(1) . . . . ?
C2 C1 C10 C11 0.000(1) . . . . ?
C12 N2 C11 C10 0.000(1) . . . . ?
C13 C10 C11 N2 0.000(1) . . . . ?
C1 C10 C11 N2 180.000(1) . . . . ?
C11 N2 C12 N3 0.000(1) . . . . ?
C11 N2 C12 C14 180.000(1) . . . . ?
N4 N3 C12 N2 180.000(1) . . . . ?
C13 N3 C12 N2 0.000(1) . . . . ?
N4 N3 C12 C14 0.000(1) . . . . ?
C13 N3 C12 C14 180.000(1) . . . . ?
C11 C10 C13 N3 0.000(1) . . . . ?
C1 C10 C13 N3 180.000(1) . . . . ?
N4 N3 C13 C10 180.000(1) . . . . ?
C12 N3 C13 C10 0.000(1) . . . . ?
N2 C12 C14 C19 180.000(1) . . . . ?
N3 C12 C14 C19 0.000(1) . . . . ?
N2 C12 C14 C15 0.000(2) . . . . ?
N3 C12 C14 C15 180.000(1) . . . . ?
C19 C14 C15 C16 0.000(2) . . . . ?
C12 C14 C15 C16 180.000(2) . . . . ?
C14 C15 C16 C17 0.000(2) . . . . ?
C15 C16 C17 C18 0.000(2) . . . . ?
C16 C17 C18 C19 0.000(2) . . . . ?
N3 N4 C19 C18 180.000(1) . . . . ?
N3 N4 C19 C14 0.000(1) . . . . ?
C17 C18 C19 N4 180.000(1) . . . . ?
C17 C18 C19 C14 0.000(2) . . . . ?
C15 C14 C19 N4 180.000(1) . . . . ?
C12 C14 C19 N4 0.000(1) . . . . ?
C15 C14 C19 C18 0.000(2) . . . . ?
C12 C14 C19 C18 180.000(1) . . . . ?

_refine_diff_density_max         0.838
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.055

