# Supplementary Information (SI) for ChemComm.
# 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_xxx
_database_code_depnum_ccdc_archive 'CCDC 2471178'
loop_
_audit_author_name
_audit_author_address
'Dr. Ruchir Kant'
;CSIR CDRI, Lucknow
India
;
_audit_update_record             
;
2025-07-09 deposited with the CCDC.	2025-09-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H9 N3 O2'
_chemical_formula_weight         179.18

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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_as_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                   12.8099(4)
_cell_length_b                   7.7737(2)
_cell_length_c                   18.5183(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1844.06(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2228
_cell_measurement_theta_min      4.7810
_cell_measurement_theta_max      75.6040

_exptl_crystal_description       Rod
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.8305
_exptl_absorpt_correction_T_max  0.9686
#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000

_diffrn_reflns_number            3952
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.78
_diffrn_reflns_theta_max         77.29
_reflns_number_total             1605
_reflns_number_gt                1339
_reflns_threshold_expression     >2sigma(I)

_audit_creation_date             2025-06-25

_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'



_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_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 > 2sigma(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)+(0.0685P)²+0.1852P] 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         1605
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS


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
C1 C 0.37510(13) 0.72860(18) 0.47757(8) 0.0521(4) Uani 1 1 d . . .
C2 C 0.46963(15) 0.7585(2) 0.51095(10) 0.0644(5) Uani 1 1 d . . .
H2 H 0.5174 0.8338 0.4902 0.077 Uiso 1 1 calc R . .
C3 C 0.4936(2) 0.6772(3) 0.57495(11) 0.0815(6) Uani 1 1 d . . .
H3 H 0.5580 0.6959 0.5968 0.098 Uiso 1 1 calc R . .
C4 C 0.4223(2) 0.5687(3) 0.60638(10) 0.0855(7) Uani 1 1 d . . .
H4 H 0.4380 0.5156 0.6501 0.103 Uiso 1 1 calc R . .
C5 C 0.3274(2) 0.5379(3) 0.57337(11) 0.0800(6) Uani 1 1 d . . .
H5 H 0.2797 0.4634 0.5947 0.096 Uiso 1 1 calc R . .
C6 C 0.30277(17) 0.6177(2) 0.50844(9) 0.0648(5) Uani 1 1 d . . .
H6 H 0.2390 0.5973 0.4860 0.078 Uiso 1 1 calc R . .
C10 C 0.18329(13) 0.82191(18) 0.27320(8) 0.0502(4) Uani 1 1 d . . .
C12 C 0.07558(19) 0.9230(3) 0.18021(12) 0.0846(6) Uani 1 1 d . . .
H12A H 0.0918 0.8316 0.1472 0.127 Uiso 1 1 calc R . .
H12B H 0.0621 1.0266 0.1536 0.127 Uiso 1 1 calc R . .
H12C H 0.0149 0.8928 0.2079 0.127 Uiso 1 1 calc R . .
N7 N 0.35650(11) 0.82348(15) 0.41269(7) 0.0548(4) Uani 1 1 d . . .
N8 N 0.28457(10) 0.76413(15) 0.37498(6) 0.0502(4) Uani 1 1 d . . .
N9 N 0.26466(12) 0.86591(15) 0.31680(7) 0.0568(4) Uani 1 1 d . . .
H9 H 0.3022 0.9551 0.3079 0.068 Uiso 1 1 calc R . .
O11 O 0.16285(11) 0.95029(15) 0.22833(7) 0.0709(4) Uani 1 1 d . . .
O13 O 0.13706(10) 0.68743(14) 0.27518(6) 0.0602(4) Uani 1 1 d . . .


_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 C2 1.379(2) . ?
C1 C6 1.388(3) . ?
C1 N7 1.430(2) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C10 O13 1.202(2) . ?
C10 O11 1.3247(18) . ?
C10 N9 1.362(2) . ?
C12 O11 1.445(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N7 N8 1.2448(19) . ?
N8 N9 1.3608(17) . ?
N9 H9 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
C2 C1 C6 120.40(16) . . ?
C2 C1 N7 115.84(15) . . ?
C6 C1 N7 123.71(15) . . ?
C3 C2 C1 120.28(19) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.30(18) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O13 C10 O11 125.24(15) . . ?
O13 C10 N9 125.25(13) . . ?
O11 C10 N9 109.51(13) . . ?
O11 C12 H12A 109.5 . . ?
O11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N8 N7 C1 113.80(12) . . ?
N7 N8 N9 111.55(12) . . ?
N8 N9 C10 117.83(12) . . ?
N8 N9 H9 121.1 . . ?
C10 N9 H9 121.1 . . ?
C10 O11 C12 115.41(14) . . ?

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 0.6(2) . . . . ?
N7 C1 C2 C3 178.04(15) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
N7 C1 C6 C5 -177.16(15) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C2 C1 N7 N8 163.08(14) . . . . ?
C6 C1 N7 N8 -19.6(2) . . . . ?
C1 N7 N8 N9 175.37(12) . . . . ?
N7 N8 N9 C10 -176.03(14) . . . . ?
O13 C10 N9 N8 -11.8(2) . . . . ?
O11 C10 N9 N8 168.13(13) . . . . ?
O13 C10 O11 C12 1.8(2) . . . . ?
N9 C10 O11 C12 -178.11(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.822
_diffrn_reflns_theta_full        77.29
_diffrn_measured_fraction_theta_full 0.822
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.029


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#                         END of data
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