# Supplementary Information (SI) for RSC Advances.
# 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_2025_Uniandes_Cu_74_CJS04-JC_Compound_3i
_database_code_depnum_ccdc_archive 'CCDC 2483802'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2025-08-30 deposited with the CCDC.	2025-12-15 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         'C10 H8 N2 O2'
_chemical_formula_sum            'C10 H8 N2 O2'
_chemical_formula_weight         188.18

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.7404(17)
_cell_length_b                   7.146(2)
_cell_length_c                   10.511(2)
_cell_angle_alpha                105.94(2)
_cell_angle_beta                 97.682(19)
_cell_angle_gamma                111.43(3)
_cell_volume                     437.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1240
_cell_measurement_theta_min      4.4960
_cell_measurement_theta_max      76.0960

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             196
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.850
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'SuperNova (Cu) micro-focus sealed X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6144
_diffrn_reflns_number            4333
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.533
_diffrn_reflns_theta_max         76.834
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1791
_reflns_number_gt                1336
_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 1.171.41.119a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1131P)²+0.0026P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_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         1791
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1948
_refine_ls_wR_factor_gt          0.1696
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
O14 O 0.4910(3) 0.6178(3) 0.88582(16) 0.0600(5) Uani 1 1 d . . . . .
H14 H 0.619173 0.652426 0.925464 0.090 Uiso 1 1 calc R U . . .
O10 O -0.0812(3) -0.2625(3) 0.00641(19) 0.0765(6) Uani 1 1 d . . . . .
C4 C 0.4451(3) 0.4860(3) 0.7548(2) 0.0460(5) Uani 1 1 d . . . . .
C1 C 0.3284(3) 0.2179(3) 0.4793(2) 0.0429(5) Uani 1 1 d . . . . .
C8 C 0.1118(3) -0.0047(3) 0.2286(2) 0.0438(5) Uani 1 1 d . . . . .
N11 N 0.2822(3) -0.1638(3) 0.06852(19) 0.0609(6) Uani 1 1 d . . . . .
H11A H 0.279013 -0.250340 -0.007813 0.073 Uiso 1 1 calc R U . . .
H11B H 0.405254 -0.084603 0.130112 0.073 Uiso 1 1 calc R U . . .
C12 C -0.0839(3) 0.0311(4) 0.2331(2) 0.0499(5) Uani 1 1 d . . . . .
C2 C 0.5382(3) 0.2883(3) 0.5665(2) 0.0452(5) Uani 1 1 d . . . . .
H2 H 0.640780 0.245302 0.532030 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2874(3) 0.0817(3) 0.3390(2) 0.0436(5) Uani 1 1 d . . . . .
H7 H 0.403774 0.047198 0.321600 0.052 Uiso 1 1 calc R U . . .
C3 C 0.5968(3) 0.4196(3) 0.7023(2) 0.0468(5) Uani 1 1 d . . . . .
H3 H 0.736497 0.463157 0.758035 0.056 Uiso 1 1 calc R U . . .
C5 C 0.2347(3) 0.4180(4) 0.6700(2) 0.0505(5) Uani 1 1 d . . . . .
H5 H 0.132922 0.461696 0.705036 0.061 Uiso 1 1 calc R U . . .
N13 N -0.2394(3) 0.0600(4) 0.2349(2) 0.0664(6) Uani 1 1 d . . . . .
C6 C 0.1776(3) 0.2866(4) 0.5352(2) 0.0499(5) Uani 1 1 d . . . . .
H6 H 0.037318 0.242671 0.480074 0.060 Uiso 1 1 calc R U . . .
C9 C 0.0977(3) -0.1527(4) 0.0912(2) 0.0494(5) 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
O14 C4 1.357(2) . ?
O14 H14 0.8200 . ?
O10 C9 1.225(3) . ?
C4 C3 1.391(3) . ?
C4 C5 1.401(3) . ?
C1 C2 1.405(3) . ?
C1 C6 1.409(3) . ?
C1 C7 1.450(3) . ?
C8 C7 1.354(3) . ?
C8 C12 1.437(3) . ?
C8 C9 1.504(3) . ?
N11 C9 1.323(3) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
C12 N13 1.141(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 H6 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
C4 O14 H14 109.5 . . ?
O14 C4 C3 123.15(19) . . ?
O14 C4 C5 117.17(17) . . ?
C3 C4 C5 119.68(19) . . ?
C2 C1 C6 117.39(18) . . ?
C2 C1 C7 116.76(17) . . ?
C6 C1 C7 125.85(18) . . ?
C7 C8 C12 122.80(18) . . ?
C7 C8 C9 123.94(16) . . ?
C12 C8 C9 113.23(17) . . ?
C9 N11 H11A 120.0 . . ?
C9 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
N13 C12 C8 179.0(3) . . ?
C3 C2 C1 121.97(17) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C8 C7 C1 132.22(16) . . ?
C8 C7 H7 113.9 . . ?
C1 C7 H7 113.9 . . ?
C2 C3 C4 119.51(18) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C6 C5 C4 120.40(18) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 121.05(19) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
O10 C9 N11 122.2(2) . . ?
O10 C9 C8 120.09(18) . . ?
N11 C9 C8 117.67(19) . . ?

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 0.1(3) . . . . ?
C7 C1 C2 C3 179.69(19) . . . . ?
C12 C8 C7 C1 0.9(4) . . . . ?
C9 C8 C7 C1 -177.0(2) . . . . ?
C2 C1 C7 C8 -176.6(2) . . . . ?
C6 C1 C7 C8 2.9(4) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
O14 C4 C3 C2 -178.74(19) . . . . ?
C5 C4 C3 C2 0.5(3) . . . . ?
O14 C4 C5 C6 179.0(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C7 C1 C6 C5 -179.4(2) . . . . ?
C7 C8 C9 O10 163.3(2) . . . . ?
C12 C8 C9 O10 -14.7(3) . . . . ?
C7 C8 C9 N11 -14.5(3) . . . . ?
C12 C8 C9 N11 167.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O14 H14 O10 0.82 1.88 2.698(2) 176.1 1_666 yes
N11 H11A O14 0.86 2.24 2.964(2) 142.0 1_544 yes
N11 H11B N13 0.86 2.21 3.033(3) 160.6 1_655 yes
C3 H3 O10 0.93 2.60 3.262(3) 129.0 1_666 yes

_refine_diff_density_max         0.252
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.056

