# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_IK2016
_database_code_depnum_ccdc_archive 'CCDC 2303450'
loop_
_audit_author_name
_audit_author_address
'Ikyon Kim'
;Yonsei University
South Korea
;
_audit_update_record             
;
2023-10-25 deposited with the CCDC.	2023-11-29 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 N4 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         276.30

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.3854(19)
_cell_length_b                   7.5604(8)
_cell_length_c                   20.364(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2676.7(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7035
_cell_measurement_theta_min      2.3181
_cell_measurement_theta_max      28.1070
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152

_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            21937
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         28.15
_diffrn_reflns_theta_full        28.15
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
;

_reflns_number_total             3174
_reflns_number_gt                2323
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_gt          0.2067
_refine_ls_wR_factor_ref         0.2302
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_number_reflns         3174
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1196P)²+2.4613P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.398
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2019.11.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.48247(12) 0.1819(3) 0.53394(9) 0.0463(5) Uani d . . . 1 . .
N N1 0.45402(11) 0.3597(3) 0.41369(9) 0.0304(5) Uani d . . . 1 . .
N N2 0.36855(12) 0.6586(3) 0.42624(10) 0.0324(5) Uani d . . . 1 . .
N N3 0.32982(13) 0.8170(3) 0.42583(11) 0.0386(5) Uani d . . . 1 . .
N N4 0.39275(13) 0.7718(3) 0.32896(11) 0.0386(5) Uani d . . . 1 . .
C C11 0.45150(14) 0.4793(3) 0.36044(11) 0.0316(5) Uani d . . . 1 . .
C C8 0.41318(14) 0.3910(3) 0.47217(11) 0.0313(5) Uani d . . . 1 . .
C C10 0.40630(14) 0.6355(3) 0.36845(12) 0.0318(5) Uani d . . . 1 . .
C C1 0.42335(14) 0.2681(3) 0.52890(12) 0.0324(5) Uani d . . . 1 . .
C C3 0.36143(14) 0.2556(3) 0.57967(11) 0.0316(5) Uani d . . . 1 . .
C C9 0.37142(14) 0.5409(3) 0.47814(12) 0.0342(6) Uani d . . . 1 . .
C C12 0.49656(15) 0.4131(4) 0.31086(13) 0.0392(6) Uani d . . . 1 . .
H H12 0.505494 0.465292 0.270215 0.047 Uiso calc U . R 1 . .
C C7 0.28365(15) 0.2834(4) 0.56569(13) 0.0375(6) Uani d . . . 1 . .
C C15 0.34646(15) 0.8783(3) 0.36671(13) 0.0372(6) Uani d . . . 1 . .
C C2 0.38421(17) 0.2033(4) 0.64289(12) 0.0393(6) Uani d . . . 1 . .
C C13 0.52679(16) 0.2506(4) 0.33330(14) 0.0413(6) Uani d . . . 1 . .
H H13 0.559441 0.176919 0.309615 0.05 Uiso calc U . R 1 . .
C C14 0.50023(16) 0.2188(4) 0.39570(13) 0.0384(6) Uani d . . . 1 . .
H H14 0.511319 0.120126 0.42129 0.046 Uiso calc U . R 1 . .
C C6 0.22920(16) 0.2644(4) 0.61507(14) 0.0432(7) Uani d . . . 1 . .
C C4 0.32846(19) 0.1831(4) 0.69184(13) 0.0457(7) Uani d . . . 1 . .
C C5 0.25179(19) 0.2143(4) 0.67823(14) 0.0468(7) Uani d . . . 1 . .
C C16 0.31651(19) 1.0510(4) 0.34256(16) 0.0512(8) Uani d . . . 1 . .
H H16A 0.275774 1.030615 0.311654 0.077 Uiso calc U . R 1 . .
H H16B 0.357263 1.115314 0.321531 0.077 Uiso calc U . R 1 . .
H H16C 0.297205 1.118478 0.378942 0.077 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.221(3) ?
N1 C14 . 1.384(3) ?
N1 C8 . 1.407(3) ?
N1 C11 . 1.413(3) ?
N2 C10 . 1.359(3) ?
N2 N3 . 1.374(3) ?
N2 C9 . 1.382(3) ?
N3 C15 . 1.322(3) ?
N4 C10 . 1.328(3) ?
N4 C15 . 1.373(3) ?
C11 C12 . 1.373(3) ?
C11 C10 . 1.428(3) ?
C8 C9 . 1.352(4) ?
C8 C1 . 1.493(3) ?
C1 C3 . 1.496(3) ?
C3 C7 . 1.398(4) ?
C3 C2 . 1.404(3) ?
C12 C13 . 1.412(4) ?
C12 H12 . 0.93 ?
C7 C6 . 1.389(4) ?
C15 C16 . 1.489(4) ?
C2 C4 . 1.399(4) ?
C13 C14 . 1.373(4) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C6 C5 . 1.397(4) ?
C4 C5 . 1.382(5) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 N1 C8 . . 130.3(2) ?
C14 N1 C11 . . 107.9(2) ?
C8 N1 C11 . . 121.8(2) ?
C10 N2 N3 . . 110.09(19) ?
C10 N2 C9 . . 124.2(2) ?
N3 N2 C9 . . 125.7(2) ?
C15 N3 N2 . . 101.8(2) ?
C10 N4 C15 . . 102.7(2) ?
C12 C11 N1 . . 108.2(2) ?
C12 C11 C10 . . 134.4(2) ?
N1 C11 C10 . . 117.3(2) ?
C9 C8 N1 . . 119.2(2) ?
C9 C8 C1 . . 121.1(2) ?
N1 C8 C1 . . 119.4(2) ?
N4 C10 N2 . . 109.8(2) ?
N4 C10 C11 . . 132.1(2) ?
N2 C10 C11 . . 118.1(2) ?
O1 C1 C8 . . 119.8(2) ?
O1 C1 C3 . . 120.9(2) ?
C8 C1 C3 . . 119.3(2) ?
C7 C3 C2 . . 120.1(2) ?
C7 C3 C1 . . 123.1(2) ?
C2 C3 C1 . . 116.7(2) ?
C8 C9 N2 . . 119.4(2) ?
C11 C12 C13 . . 107.0(2) ?
C11 C12 H12 . . 126.5 ?
C13 C12 H12 . . 126.5 ?
C6 C7 C3 . . 119.8(2) ?
N3 C15 N4 . . 115.6(2) ?
N3 C15 C16 . . 122.1(3) ?
N4 C15 C16 . . 122.3(2) ?
C4 C2 C3 . . 119.3(3) ?
C14 C13 C12 . . 109.1(2) ?
C14 C13 H13 . . 125.5 ?
C12 C13 H13 . . 125.5 ?
C13 C14 N1 . . 107.8(2) ?
C13 C14 H14 . . 126.1 ?
N1 C14 H14 . . 126.1 ?
C7 C6 C5 . . 120.2(3) ?
C5 C4 C2 . . 120.5(3) ?
C4 C5 C6 . . 120.1(3) ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?

