# Electronic Supplementary Material (ESI) for Analytical Methods.
# 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_skaj30
_database_code_depnum_ccdc_archive 'CCDC 2075676'
loop_
_audit_author_name
_audit_author_address
'Atanu Jana'
;Dongguk University
South Korea
;
_audit_update_record             
;
2021-04-05 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_skaj30              
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.934 Why?
RESPONSE: Low quality single crystal
;
# Added during the CSD deposition process: Monday 05 April 2021 10:29 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N5 O3'
_chemical_formula_sum            'C17 H15 N5 O3'
_chemical_formula_weight         337.34

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'I 41/a'
_symmetry_space_group_name_Hall  '-I 4ad'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z'
'-y+3/4, x+1/4, z+1/4'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-1/4'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   19.559(2)
_cell_length_b                   19.559(2)
_cell_length_c                   16.966(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6490.4(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14751
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      25.9

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2816.0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.9893
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14751
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         25.89
_reflns_number_total             2939
_reflns_number_gt                1798
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WINGX V1.80.05'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0532P)²+1.2521P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2939
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1150
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.12479(8) 0.00309(8) 0.95026(8) 0.0535(4) Uani 1 1 d . . .
N2 N 0.08216(8) -0.04199(7) 0.98662(8) 0.0517(4) Uani 1 1 d . . .
O1 O 0.14627(8) 0.02164(8) 0.74389(7) 0.0785(5) Uani 1 1 d . . .
O2 O 0.27275(8) 0.15112(8) 0.65056(8) 0.0777(5) Uani 1 1 d . . .
C5 C 0.08290(10) -0.04333(9) 1.07050(10) 0.0509(5) Uani 1 1 d . . .
N4 N 0.19942(9) 0.07627(9) 0.84368(10) 0.0621(5) Uani 1 1 d . . .
N5 N 0.23834(9) 0.11402(9) 0.79224(9) 0.0617(5) Uani 1 1 d . . .
N1 N 0.03764(9) -0.08300(9) 1.10426(10) 0.0714(5) Uani 1 1 d . . .
C10 C 0.15430(11) 0.03075(10) 0.81456(10) 0.0566(5) Uani 1 1 d . . .
O3 O 0.35356(10) 0.22784(10) 0.55901(9) 0.0914(6) Uani 1 1 d . . .
C12 C 0.32214(10) 0.19869(10) 0.76895(11) 0.0598(5) Uani 1 1 d . . .
C9 C 0.11566(10) -0.00822(9) 0.87384(10) 0.0525(5) Uani 1 1 d . . .
C11 C 0.27990(11) 0.15779(11) 0.82076(11) 0.0638(6) Uani 1 1 d . . .
H11 H 0.2831 0.1634 0.8751 0.077 Uiso 1 1 calc R . .
C7 C 0.04685(10) -0.08134(10) 0.93318(11) 0.0556(5) Uani 1 1 d . . .
C14 C 0.35893(11) 0.23311(12) 0.63906(12) 0.0676(6) Uani 1 1 d . . .
C4 C 0.12913(12) -0.00466(12) 1.11100(12) 0.0745(6) Uani 1 1 d . . .
H4 H 0.1597 0.0237 1.0846 0.089 Uiso 1 1 calc R . .
C13 C 0.31721(10) 0.19352(10) 0.68752(11) 0.0591(5) Uani 1 1 d . . .
C2 C 0.08364(13) -0.04921(11) 1.22824(12) 0.0732(6) Uani 1 1 d . . .
H2A H 0.0827 -0.0527 1.2829 0.088 Uiso 1 1 calc R . .
C8 C 0.06795(10) -0.06013(10) 0.86082(11) 0.0612(5) Uani 1 1 d . . .
H8 H 0.0535 -0.0769 0.8123 0.073 Uiso 1 1 calc R . .
C15 C 0.40541(12) 0.27669(13) 0.67123(14) 0.0865(8) Uani 1 1 d . . .
H15 H 0.4335 0.3028 0.6388 0.104 Uiso 1 1 calc R . .
C1 C 0.03918(13) -0.08468(12) 1.18288(13) 0.0837(7) Uani 1 1 d . . .
H1 H 0.0073 -0.1122 1.2083 0.100 Uiso 1 1 calc R . .
C3 C 0.12935(13) -0.00865(12) 1.19165(12) 0.0804(7) Uani 1 1 d . . .
H3A H 0.1608 0.0164 1.2209 0.096 Uiso 1 1 calc R . .
C17 C 0.36954(12) 0.24410(13) 0.80034(13) 0.0831(7) Uani 1 1 d . . .
H17 H 0.3733 0.2487 0.8547 0.100 Uiso 1 1 calc R . .
C6 C -0.00330(12) -0.13606(12) 0.95343(13) 0.0788(7) Uani 1 1 d . . .
H6A H -0.0199 -0.1569 0.9059 0.118 Uiso 1 1 calc R . .
H6B H -0.0409 -0.1165 0.9819 0.118 Uiso 1 1 calc R . .
H6C H 0.0186 -0.1700 0.9855 0.118 Uiso 1 1 calc R . .
C16 C 0.41074(14) 0.28202(15) 0.75208(15) 0.1011(9) Uani 1 1 d . . .
H16 H 0.4427 0.3117 0.7740 0.121 Uiso 1 1 calc R . .
H4N H 0.2071(9) 0.0798(9) 0.8938(12) 0.061(6) Uiso 1 1 d . . .
H3 H 0.3229(17) 0.1955(16) 0.547(2) 0.164(16) Uiso 1 1 d . . .
H2 H 0.2474(17) 0.1262(16) 0.692(2) 0.160(12) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
N3 C9 1.327(2) . ?
N3 N2 1.3613(19) . ?
N2 C7 1.375(2) . ?
N2 C5 1.423(2) . ?
O1 C10 1.222(2) . ?
O2 C13 1.355(2) . ?
O2 H2 0.99(3) . ?
C5 N1 1.309(2) . ?
C5 C4 1.364(3) . ?
N4 C10 1.348(3) . ?
N4 N5 1.373(2) . ?
N4 H4N 0.87(2) . ?
N5 C11 1.276(2) . ?
N1 C1 1.335(3) . ?
C10 C9 1.471(3) . ?
O3 C14 1.366(2) . ?
O3 H3 0.90(3) . ?
C12 C13 1.389(3) . ?
C12 C17 1.390(3) . ?
C12 C11 1.447(3) . ?
C9 C8 1.397(3) . ?
C11 H11 0.9300 . ?
C7 C8 1.360(3) . ?
C7 C6 1.492(3) . ?
C14 C15 1.361(3) . ?
C14 C13 1.393(3) . ?
C4 C3 1.371(3) . ?
C4 H4 0.9300 . ?
C2 C3 1.347(3) . ?
C2 C1 1.353(3) . ?
C2 H2A 0.9300 . ?
C8 H8 0.9300 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C1 H1 0.9300 . ?
C3 H3A 0.9300 . ?
C17 C16 1.367(3) . ?
C17 H17 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C16 H16 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 N3 N2 104.62(14) . . ?
N3 N2 C7 111.79(14) . . ?
N3 N2 C5 117.31(14) . . ?
C7 N2 C5 130.83(16) . . ?
C13 O2 H2 106.8(19) . . ?
N1 C5 C4 123.80(17) . . ?
N1 C5 N2 116.20(17) . . ?
C4 C5 N2 120.00(17) . . ?
C10 N4 N5 119.03(16) . . ?
C10 N4 H4N 121.8(12) . . ?
N5 N4 H4N 119.0(12) . . ?
C11 N5 N4 118.22(16) . . ?
C5 N1 C1 115.89(18) . . ?
O1 C10 N4 122.69(19) . . ?
O1 C10 C9 121.96(19) . . ?
N4 C10 C9 115.35(16) . . ?
C14 O3 H3 109(2) . . ?
C13 C12 C17 118.30(19) . . ?
C13 C12 C11 121.62(19) . . ?
C17 C12 C11 120.08(18) . . ?
N3 C9 C8 111.44(17) . . ?
N3 C9 C10 120.83(17) . . ?
C8 C9 C10 127.72(17) . . ?
N5 C11 C12 120.28(18) . . ?
N5 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C8 C7 N2 105.78(17) . . ?
C8 C7 C6 128.77(18) . . ?
N2 C7 C6 125.44(17) . . ?
C15 C14 O3 119.8(2) . . ?
C15 C14 C13 120.2(2) . . ?
O3 C14 C13 120.0(2) . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
O2 C13 C12 123.33(18) . . ?
O2 C13 C14 116.28(18) . . ?
C12 C13 C14 120.4(2) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2A 121.1 . . ?
C1 C2 H2A 121.1 . . ?
C7 C8 C9 106.37(17) . . ?
C7 C8 H8 126.8 . . ?
C9 C8 H8 126.8 . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
N1 C1 C2 124.8(2) . . ?
N1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C16 C17 C12 120.7(2) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        25.89
_diffrn_measured_fraction_theta_full 0.934
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.030
