# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2388769'
loop_
_audit_author_name
_audit_author_address
'Dhiraj Brahman'
;St Josephs College Darjeeling
India
;
_audit_update_record             
;
2024-10-04 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'1-hydroxy-2-(naphthalen-1-yl)-1H-imidazole 3-oxide'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N2 O2'
_chemical_formula_sum            'C13 H10 N2 O2'
_chemical_formula_weight         226.23

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'

_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                   8.9333(5)
_cell_length_b                   10.9751(6)
_cell_length_c                   11.0707(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.371(2)
_cell_angle_gamma                90
_cell_volume                     1085.39(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    304(2)
_cell_measurement_reflns_used    1878
_cell_measurement_theta_min      2.613
_cell_measurement_theta_max      25.035

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.536
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79924
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      304(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27414
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.613
_diffrn_reflns_theta_max         25.035
_diffrn_reflns_theta_full        25.035
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1923
_reflns_number_gt                1693
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'WinGX v2018.3'
_computing_publication_material  'WinGX v2018.3'
_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)+(0.0480P)²+0.3245P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1923
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0970
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.098
_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
O2 O 0.55324(13) 0.59977(9) 0.91301(9) 0.0386(3) Uani 1 1 d D . . . .
O1 O 0.71643(12) 0.80597(10) 0.56405(9) 0.0410(3) Uani 1 1 d . . . . .
N1 N 0.63317(13) 0.77313(11) 0.66051(10) 0.0311(3) Uani 1 1 d . . . . .
N2 N 0.56176(14) 0.68169(11) 0.82046(10) 0.0308(3) Uani 1 1 d . . . . .
C12 C 0.51238(19) 0.83579(14) 0.70350(14) 0.0386(4) Uani 1 1 d . . . . .
C11 C 0.66405(16) 0.67693(12) 0.73114(12) 0.0279(3) Uani 1 1 d . . . . .
C1 C 0.78228(16) 0.58442(12) 0.72020(13) 0.0295(3) Uani 1 1 d . . . . .
C10 C 0.79277(15) 0.50906(12) 0.61536(13) 0.0290(3) Uani 1 1 d . . . . .
C9 C 0.69707(16) 0.52038(14) 0.51373(13) 0.0334(3) Uani 1 1 d . . . . .
C8 C 0.70844(19) 0.44261(16) 0.41833(15) 0.0428(4) Uani 1 1 d . . . . .
C7 C 0.8174(2) 0.35011(16) 0.41744(17) 0.0493(5) Uani 1 1 d . . . . .
C13 C 0.46766(19) 0.77738(15) 0.80451(14) 0.0386(4) Uani 1 1 d . . . . .
C5 C 0.90330(17) 0.41542(13) 0.61463(15) 0.0364(4) Uani 1 1 d . . . . .
C4 C 0.99945(19) 0.40182(16) 0.71585(17) 0.0459(4) Uani 1 1 d . . . . .
C3 C 0.9872(2) 0.47464(17) 0.81393(16) 0.0466(4) Uani 1 1 d . . . . .
C2 C 0.87708(18) 0.56618(15) 0.81689(14) 0.0384(4) Uani 1 1 d . . . . .
C6 C 0.9125(2) 0.33780(15) 0.51263(17) 0.0468(4) Uani 1 1 d . . . . .
H12 H 0.477(2) 0.9059(17) 0.6636(16) 0.048(5) Uiso 1 1 d . . . . .
H2 H 0.866(2) 0.6189(18) 0.8889(17) 0.052(5) Uiso 1 1 d . . . . .
H9 H 0.6253(19) 0.5839(15) 0.5127(14) 0.034(4) Uiso 1 1 d . . . . .
H4 H 1.071(2) 0.3404(18) 0.7138(17) 0.053(5) Uiso 1 1 d . . . . .
H13 H 0.389(2) 0.7922(16) 0.8594(16) 0.046(5) Uiso 1 1 d . . . . .
H3 H 1.055(2) 0.4671(18) 0.8841(18) 0.058(5) Uiso 1 1 d . . . . .
H8 H 0.646(2) 0.4525(17) 0.3492(17) 0.050(5) Uiso 1 1 d . . . . .
H7 H 0.823(2) 0.2954(18) 0.3466(18) 0.055(5) Uiso 1 1 d . . . . .
H6 H 0.989(2) 0.2740(19) 0.5140(18) 0.061(6) Uiso 1 1 d . . . . .
H2A H 0.615(2) 0.636(2) 0.9792(17) 0.077(7) Uiso 1 1 d 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
O2 N2 1.3657(15) . ?
O2 H2A 0.999(16) . ?
O1 N1 1.3542(15) . ?
N1 C11 1.3414(18) . ?
N1 C12 1.368(2) . ?
N2 C11 1.3518(18) . ?
N2 C13 1.356(2) . ?
C12 C13 1.352(2) . ?
C12 H12 0.940(19) . ?
C11 C1 1.4706(19) . ?
C1 C2 1.375(2) . ?
C1 C10 1.429(2) . ?
C10 C9 1.414(2) . ?
C10 C5 1.425(2) . ?
C9 C8 1.362(2) . ?
C9 H9 0.947(17) . ?
C8 C7 1.407(2) . ?
C8 H8 0.952(19) . ?
C7 C6 1.356(3) . ?
C7 H7 0.99(2) . ?
C13 H13 0.944(19) . ?
C5 C4 1.415(2) . ?
C5 C6 1.417(2) . ?
C4 C3 1.353(3) . ?
C4 H4 0.93(2) . ?
C3 C2 1.406(2) . ?
C3 H3 0.98(2) . ?
C2 H2 0.99(2) . ?
C6 H6 0.98(2) . ?

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
N2 O2 H2A 104.7(13) . . ?
C11 N1 O1 123.86(12) . . ?
C11 N1 C12 110.65(13) . . ?
O1 N1 C12 125.39(12) . . ?
C11 N2 C13 110.86(12) . . ?
C11 N2 O2 124.38(12) . . ?
C13 N2 O2 124.75(12) . . ?
C13 C12 N1 106.71(14) . . ?
C13 C12 H12 132.6(11) . . ?
N1 C12 H12 120.7(11) . . ?
N1 C11 N2 104.98(12) . . ?
N1 C11 C1 129.83(13) . . ?
N2 C11 C1 125.18(12) . . ?
C2 C1 C10 120.31(13) . . ?
C2 C1 C11 118.39(13) . . ?
C10 C1 C11 121.16(12) . . ?
C9 C10 C5 118.30(13) . . ?
C9 C10 C1 123.57(13) . . ?
C5 C10 C1 118.11(13) . . ?
C8 C9 C10 120.93(14) . . ?
C8 C9 H9 120.4(10) . . ?
C10 C9 H9 118.7(10) . . ?
C9 C8 C7 120.85(16) . . ?
C9 C8 H8 120.3(11) . . ?
C7 C8 H8 118.8(11) . . ?
C6 C7 C8 119.77(16) . . ?
C6 C7 H7 121.3(11) . . ?
C8 C7 H7 118.9(11) . . ?
C12 C13 N2 106.78(14) . . ?
C12 C13 H13 132.5(11) . . ?
N2 C13 H13 120.8(11) . . ?
C4 C5 C6 121.96(15) . . ?
C4 C5 C10 119.23(14) . . ?
C6 C5 C10 118.80(14) . . ?
C3 C4 C5 121.41(15) . . ?
C3 C4 H4 120.5(12) . . ?
C5 C4 H4 118.1(12) . . ?
C4 C3 C2 120.05(15) . . ?
C4 C3 H3 122.1(12) . . ?
C2 C3 H3 117.9(12) . . ?
C1 C2 C3 120.87(15) . . ?
C1 C2 H2 118.6(11) . . ?
C3 C2 H2 120.5(11) . . ?
C7 C6 C5 121.34(15) . . ?
C7 C6 H6 121.2(12) . . ?
C5 C6 H6 117.5(12) . . ?

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
C11 N1 C12 C13 0.55(17) . . . . ?
O1 N1 C12 C13 -176.09(12) . . . . ?
O1 N1 C11 N2 175.70(12) . . . . ?
C12 N1 C11 N2 -1.01(15) . . . . ?
O1 N1 C11 C1 -3.5(2) . . . . ?
C12 N1 C11 C1 179.81(14) . . . . ?
C13 N2 C11 N1 1.11(15) . . . . ?
O2 N2 C11 N1 -179.89(11) . . . . ?
C13 N2 C11 C1 -179.66(13) . . . . ?
O2 N2 C11 C1 -0.7(2) . . . . ?
N1 C11 C1 C2 124.95(16) . . . . ?
N2 C11 C1 C2 -54.1(2) . . . . ?
N1 C11 C1 C10 -59.4(2) . . . . ?
N2 C11 C1 C10 121.62(15) . . . . ?
C2 C1 C10 C9 178.45(14) . . . . ?
C11 C1 C10 C9 2.8(2) . . . . ?
C2 C1 C10 C5 0.1(2) . . . . ?
C11 C1 C10 C5 -175.51(13) . . . . ?
C5 C10 C9 C8 1.1(2) . . . . ?
C1 C10 C9 C8 -177.29(14) . . . . ?
C10 C9 C8 C7 -1.1(2) . . . . ?
C9 C8 C7 C6 0.1(3) . . . . ?
N1 C12 C13 N2 0.15(17) . . . . ?
C11 N2 C13 C12 -0.80(17) . . . . ?
O2 N2 C13 C12 -179.79(12) . . . . ?
C9 C10 C5 C4 -179.48(14) . . . . ?
C1 C10 C5 C4 -1.0(2) . . . . ?
C9 C10 C5 C6 -0.1(2) . . . . ?
C1 C10 C5 C6 178.34(14) . . . . ?
C6 C5 C4 C3 -178.38(16) . . . . ?
C10 C5 C4 C3 1.0(2) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C10 C1 C2 C3 0.9(2) . . . . ?
C11 C1 C2 C3 176.67(14) . . . . ?
C4 C3 C2 C1 -1.0(3) . . . . ?
C8 C7 C6 C5 0.9(3) . . . . ?
C4 C5 C6 C7 178.49(17) . . . . ?
C10 C5 C6 C7 -0.9(2) . . . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
