# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_tsq-dj-02
_database_code_depnum_ccdc_archive 'CCDC 2404099'
loop_
_audit_author_name
_audit_author_address
'JIanchun wang'
;Capital Normal University
China
;
_audit_update_record             
;
2024-11-20 deposited with the CCDC.	2025-01-28 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         ?
_chemical_formula_sum            'C6 H3 N4 O3'
_chemical_formula_weight         179.12

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'
O O 0.0492 0.0322 '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                   9.1663(2)
_cell_length_b                   10.7506(2)
_cell_length_c                   7.6582(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.380(2)
_cell_angle_gamma                90
_cell_volume                     720.21(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.192
_shelx_estimated_absorpt_T_min   0.755
_shelx_estimated_absorpt_T_max   0.842
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4242
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         5.056
_diffrn_reflns_theta_max         74.410
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1441
_reflns_number_gt                1228
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1299P)²+0.1553P] 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         1441
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.2122
_refine_ls_wR_factor_gt          0.2048
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.163
_refine_ls_shift/su_max          0.007
_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_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
O1 O 0.54234(17) 0.54975(15) 0.3430(2) 0.0465(5) Uani 1 1 d . . . . .
N4 N 0.3589(2) 0.46095(17) -0.1007(2) 0.0428(5) Uani 1 1 d . . . . .
N3 N 0.3839(2) 0.4849(2) 0.0755(2) 0.0456(5) Uani 1 1 d . . . . .
O2 O 0.5795(3) 0.3081(2) 0.3830(3) 0.0817(8) Uani 1 1 d . . . . .
N2 N 0.6935(2) 0.32066(19) 0.5101(3) 0.0555(6) Uani 1 1 d . . . . .
N1 N 0.8971(2) 0.4463(2) 0.6774(3) 0.0552(6) Uani 1 1 d . . . . .
C6 C 0.5239(2) 0.52290(19) 0.1662(3) 0.0378(5) Uani 1 1 d . . . . .
C2 C 0.6902(2) 0.5514(2) 0.4632(3) 0.0406(6) Uani 1 1 d . . . . .
C1 C 0.7627(3) 0.44581(19) 0.5504(3) 0.0430(6) Uani 1 1 d . . . . .
O3 O 0.7483(3) 0.2391(2) 0.6142(5) 0.1187(12) Uani 1 1 d . . . . .
C3 C 0.7620(3) 0.6636(2) 0.5115(3) 0.0528(6) Uani 1 1 d . . . . .
H3 H 0.716848 0.736796 0.456091 0.063 Uiso 1 1 calc R U . . .
C5 C 0.9648(3) 0.5557(3) 0.7234(4) 0.0625(8) Uani 1 1 d . . . . .
H5 H 1.058779 0.557866 0.813778 0.075 Uiso 1 1 calc R U . . .
C4 C 0.9030(3) 0.6662(3) 0.6442(4) 0.0618(7) Uani 1 1 d . . . . .
H4 H 0.954710 0.740849 0.678940 0.074 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0333(8) 0.0641(11) 0.0379(8) -0.0024(6) 0.0041(6) 0.0060(6)
N4 0.0322(9) 0.0526(11) 0.0401(9) 0.0007(7) 0.0054(7) -0.0028(7)
N3 0.0329(9) 0.0624(12) 0.0388(9) 0.0003(8) 0.0068(7) -0.0037(8)
O2 0.0787(14) 0.0582(12) 0.0843(14) -0.0125(10) -0.0123(11) -0.0101(9)
N2 0.0506(12) 0.0451(11) 0.0651(12) 0.0020(9) 0.0087(9) 0.0024(8)
N1 0.0396(11) 0.0617(14) 0.0545(12) 0.0024(9) -0.0006(9) 0.0072(8)
C6 0.0330(10) 0.0396(11) 0.0366(10) 0.0036(8) 0.0040(8) 0.0045(7)
C2 0.0325(11) 0.0486(12) 0.0368(10) -0.0023(8) 0.0045(8) 0.0036(7)
C1 0.0384(12) 0.0452(12) 0.0422(11) -0.0023(8) 0.0072(9) 0.0019(8)
O3 0.1041(19) 0.0588(14) 0.150(3) 0.0367(14) -0.0287(18) -0.0073(13)
C3 0.0510(13) 0.0444(12) 0.0584(13) -0.0036(10) 0.0095(11) 0.0027(9)
C5 0.0405(13) 0.0748(19) 0.0593(15) -0.0106(12) -0.0047(11) -0.0034(10)
C4 0.0513(14) 0.0588(15) 0.0685(15) -0.0153(12) 0.0074(12) -0.0115(11)

_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
O1 C6 1.345(2) . ?
O1 C2 1.392(2) . ?
N4 N3 1.325(2) . ?
N4 C6 1.326(3) 3_665 ?
N3 C6 1.328(3) . ?
O2 N2 1.204(3) . ?
N2 O3 1.190(3) . ?
N2 C1 1.480(3) . ?
N1 C1 1.322(3) . ?
N1 C5 1.328(3) . ?
C2 C3 1.372(3) . ?
C2 C1 1.382(3) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C5 C4 1.376(4) . ?
C5 H5 0.9300 . ?
C4 H4 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
C6 O1 C2 118.22(17) . . ?
N3 N4 C6 116.52(17) . 3_665 ?
N4 N3 C6 115.99(18) . . ?
O3 N2 O2 123.3(2) . . ?
O3 N2 C1 117.5(2) . . ?
O2 N2 C1 119.0(2) . . ?
C1 N1 C5 117.2(2) . . ?
N4 C6 N3 127.49(19) 3_665 . ?
N4 C6 O1 118.71(18) 3_665 . ?
N3 C6 O1 113.78(19) . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 O1 118.91(19) . . ?
C1 C2 O1 122.79(19) . . ?
N1 C1 C2 124.1(2) . . ?
N1 C1 N2 113.83(18) . . ?
C2 C1 N2 122.1(2) . . ?
C2 C3 C4 118.9(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
N1 C5 C4 123.3(2) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.3 . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?

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 N4 N3 C6 0.2(3) 3_665 . . . ?
N4 N3 C6 N4 -0.3(4) . . . 3_665 ?
N4 N3 C6 O1 178.03(16) . . . . ?
C2 O1 C6 N4 -21.8(3) . . . 3_665 ?
C2 O1 C6 N3 159.76(19) . . . . ?
C6 O1 C2 C3 100.3(2) . . . . ?
C6 O1 C2 C1 -86.3(3) . . . . ?
C5 N1 C1 C2 0.4(4) . . . . ?
C5 N1 C1 N2 -178.7(2) . . . . ?
C3 C2 C1 N1 -0.1(4) . . . . ?
O1 C2 C1 N1 -173.6(2) . . . . ?
C3 C2 C1 N2 179.0(2) . . . . ?
O1 C2 C1 N2 5.4(4) . . . . ?
O3 N2 C1 N1 13.2(4) . . . . ?
O2 N2 C1 N1 -171.9(2) . . . . ?
O3 N2 C1 C2 -165.9(3) . . . . ?
O2 N2 C1 C2 8.9(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
O1 C2 C3 C4 173.9(2) . . . . ?
C1 N1 C5 C4 -0.9(5) . . . . ?
N1 C5 C4 C3 0.9(5) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?

_refine_diff_density_max         0.453
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.144

_shelx_res_file                  
;
TITL tsq-dj-02_a.res in P2(1)/c
    tsq-dj-02.res
    created by SHELXL-2018/3 at 21:35:17 on 13-Apr-2021
REM Old TITL tsq-dj-02 in P21/c #14
REM SHELXT solution in P2(1)/c: R1 0.217, Rweak 0.178, Alpha 0.033
REM <I/s> 0.550 for 86 systematic absences, Orientation as input
REM Formula found by SHELXT: C10 N O2
CELL 1.54184 9.1663 10.7506 7.6582 90 107.38 90
ZERR 4 0.0002 0.0002 0.0002 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 24 12 16 12

L.S. 2
PLAN  5
SIZE 0.2 0.15 0.25
CONF
BOND
list 4
fmap 2
MORE -1
BOND $H
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\tsq-dj-02.hkl">
REM </olex2.extras>

WGHT    0.129900    0.155300
FVAR       1.01330
O1    4    0.542344    0.549753    0.343032    11.00000    0.03326    0.06415 =
         0.03789   -0.00237    0.00407    0.00596
N4    3    0.358858    0.460950   -0.100688    11.00000    0.03219    0.05259 =
         0.04006    0.00068    0.00540   -0.00280
N3    3    0.383871    0.484919    0.075531    11.00000    0.03292    0.06244 =
         0.03881    0.00027    0.00676   -0.00367
O2    4    0.579457    0.308098    0.383005    11.00000    0.07872    0.05816 =
         0.08425   -0.01249   -0.01235   -0.01013
N2    3    0.693472    0.320657    0.510140    11.00000    0.05062    0.04510 =
         0.06511    0.00196    0.00868    0.00241
N1    3    0.897115    0.446301    0.677391    11.00000    0.03965    0.06171 =
         0.05452    0.00236   -0.00059    0.00721
C6    1    0.523903    0.522903    0.166159    11.00000    0.03300    0.03962 =
         0.03655    0.00356    0.00402    0.00447
C2    1    0.690177    0.551387    0.463180    11.00000    0.03254    0.04863 =
         0.03677   -0.00230    0.00451    0.00360
C1    1    0.762687    0.445811    0.550363    11.00000    0.03843    0.04519 =
         0.04224   -0.00227    0.00717    0.00194
O3    4    0.748321    0.239096    0.614154    11.00000    0.10408    0.05880 =
         0.14963    0.03668   -0.02871   -0.00726
C3    1    0.762010    0.663641    0.511476    11.00000    0.05102    0.04441 =
         0.05843   -0.00363    0.00949    0.00266
AFIX  43
H3    2    0.716848    0.736796    0.456091    11.00000   -1.20000
AFIX   0
C5    1    0.964831    0.555740    0.723427    11.00000    0.04046    0.07485 =
         0.05925   -0.01057   -0.00474   -0.00335
AFIX  43
H5    2    1.058779    0.557866    0.813778    11.00000   -1.20000
AFIX   0
C4    1    0.902991    0.666163    0.644176    11.00000    0.05132    0.05877 =
         0.06848   -0.01526    0.00742   -0.01153
AFIX  43
H4    2    0.954710    0.740849    0.678940    11.00000   -1.20000
AFIX   0
HKLF 4




REM  tsq-dj-02_a.res in P2(1)/c
REM wR2 = 0.2122, GooF = S = 1.163, Restrained GooF = 1.163 for all data
REM R1 = 0.0746 for 1228 Fo > 4sig(Fo) and 0.0803 for all 1441 data
REM 118 parameters refined using 0 restraints

END

WGHT      0.1299      0.1553

REM Highest difference peak  0.453,  deepest hole -0.524,  1-sigma level  0.144
Q1    1   0.8111  0.2377  0.5046  11.00000  0.05    0.45
Q2    1   0.8995  0.6054  0.3833  11.00000  0.05    0.29
Q3    1   0.9321  0.6781  0.4020  11.00000  0.05    0.28
Q4    1   0.7986  0.2984  0.8531  11.00000  0.05    0.27
Q5    1   1.1095  0.4995  0.6036  11.00000  0.05    0.27
;
_shelx_res_checksum              51069
