# Supplementary Information (SI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_app1_a
_database_code_depnum_ccdc_archive 'CCDC 2467508'
loop_
_audit_author_name
_audit_author_address
'Tridib Ranjan Nath'
;NIT SILCHAR
India
;
_audit_update_record             
;
2025-06-26 deposited with the CCDC.	2026-03-03 downloaded from the CCDC.
;
_audit_creation_date             2025-06-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
1-((E)-(((Z)-3,5-difluoro-2-hydroxybenzylidene)hydrazineylidene)methyl)naphthalen-2-ol
_chemical_formula_moiety         'C18 H12 F2 N2 O2'
_chemical_formula_sum            'C18 H12 F2 N2 O2'
_chemical_formula_weight         326.30
_chemical_melting_point          296
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.730(7)
_cell_length_b                   7.121(3)
_cell_length_c                   13.227(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.664(11)
_cell_angle_gamma                90
_cell_volume                     1464.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2119
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.61
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5929
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1020 before and 0.0715 after correction.
The Ratio of minimum to maximum transmission is 0.7951.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.045
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1289
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            40282
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.176
_diffrn_reflns_theta_min         2.620
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1478
_reflns_number_total             3576
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0130(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1635
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+0.2556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1662
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C6(H6), C8(H8), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F1 F 0.81742(10) 0.9856(3) 0.64068(14) 0.0752(6) Uani 1 1 d . . . . .
F2 F 0.65434(11) 0.9119(3) 0.85838(13) 0.0859(6) Uani 1 1 d . . . . .
O1 O 0.51908(12) 0.7928(3) 0.69169(15) 0.0687(6) Uani 1 1 d . . . . .
H1 H 0.482008 0.755739 0.635053 0.103 Uiso 1 1 calc R U . . .
O2 O 0.31616(13) 0.6019(3) 0.17745(15) 0.0725(6) Uani 1 1 d . . . . .
H2 H 0.355792 0.632154 0.233470 0.109 Uiso 1 1 calc R U . . .
N1 N 0.45532(13) 0.7194(3) 0.48327(17) 0.0453(6) Uani 1 1 d . . . . .
N2 N 0.39156(13) 0.6666(3) 0.38467(17) 0.0472(6) Uani 1 1 d . . . . .
C1 C 0.59817(15) 0.8275(3) 0.5709(2) 0.0394(6) Uani 1 1 d . . . . .
C2 C 0.32030(16) 0.6253(3) 0.3954(2) 0.0436(6) Uani 1 1 d . . . . .
H2A H 0.317068 0.633392 0.463966 0.052 Uiso 1 1 calc R U . . .
C3 C 0.16811(16) 0.5134(3) 0.3216(2) 0.0462(7) Uani 1 1 d . . . . .
C4 C 0.24494(16) 0.5665(3) 0.3043(2) 0.0438(6) Uani 1 1 d . . . . .
C5 C 0.52644(16) 0.7674(3) 0.4756(2) 0.0437(6) Uani 1 1 d . . . . .
H5 H 0.532183 0.763605 0.408377 0.052 Uiso 1 1 calc R U . . .
C6 C 0.67492(16) 0.8790(3) 0.5610(2) 0.0469(7) Uani 1 1 d . . . . .
H6 H 0.680273 0.875055 0.493500 0.056 Uiso 1 1 calc R U . . .
C7 C 0.74266(16) 0.9354(4) 0.6511(2) 0.0492(7) Uani 1 1 d . . . . .
C8 C 0.73758(17) 0.9475(4) 0.7513(2) 0.0520(7) Uani 1 1 d . . . . .
H8 H 0.784200 0.987008 0.811610 0.062 Uiso 1 1 calc R U . . .
C9 C 0.59076(16) 0.8379(4) 0.6731(2) 0.0466(7) Uani 1 1 d . . . . .
C10 C 0.24666(18) 0.5564(4) 0.2009(2) 0.0537(7) Uani 1 1 d . . . . .
C11 C 0.09664(17) 0.4461(4) 0.2321(3) 0.0549(8) Uani 1 1 d . . . . .
C12 C 0.66193(18) 0.8995(4) 0.7595(2) 0.0532(7) Uani 1 1 d . . . . .
C13 C 0.15903(17) 0.5204(4) 0.4232(2) 0.0582(8) Uani 1 1 d . . . . .
H13 H 0.204270 0.565768 0.483260 0.070 Uiso 1 1 calc R U . . .
C14 C 0.02181(18) 0.3884(4) 0.2486(3) 0.0672(9) Uani 1 1 d . . . . .
H14 H -0.024808 0.344339 0.189748 0.081 Uiso 1 1 calc R U . . .
C15 C 0.10300(19) 0.4410(4) 0.1286(3) 0.0680(9) Uani 1 1 d . . . . .
H15 H 0.056024 0.398998 0.069495 0.082 Uiso 1 1 calc R U . . .
C16 C 0.0160(2) 0.3952(4) 0.3470(3) 0.0742(10) Uani 1 1 d . . . . .
H16 H -0.033869 0.355503 0.356165 0.089 Uiso 1 1 calc R U . . .
C17 C 0.08552(19) 0.4624(5) 0.4356(3) 0.0723(9) Uani 1 1 d . . . . .
H17 H 0.081660 0.467744 0.503886 0.087 Uiso 1 1 calc R U . . .
C18 C 0.1740(2) 0.4943(4) 0.1123(3) 0.0699(9) Uani 1 1 d . . . . .
H18 H 0.175494 0.490512 0.042752 0.084 Uiso 1 1 calc R U . . .


_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
F1 C7 1.356(3) . ?
F2 C12 1.362(3) . ?
O1 H1 0.8200 . ?
O1 C9 1.349(3) . ?
O2 H2 0.8200 . ?
O2 C10 1.349(3) . ?
N1 N2 1.398(3) . ?
N1 C5 1.277(3) . ?
N2 C2 1.286(3) . ?
C1 C5 1.447(3) . ?
C1 C6 1.387(3) . ?
C1 C9 1.404(3) . ?
C2 H2A 0.9300 . ?
C2 C4 1.448(3) . ?
C3 C4 1.437(3) . ?
C3 C11 1.420(4) . ?
C3 C13 1.407(4) . ?
C4 C10 1.380(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.367(3) . ?
C7 C8 1.361(4) . ?
C8 H8 0.9300 . ?
C8 C12 1.354(4) . ?
C9 C12 1.383(4) . ?
C10 C18 1.412(4) . ?
C11 C14 1.409(4) . ?
C11 C15 1.412(4) . ?
C13 H13 0.9300 . ?
C13 C17 1.364(4) . ?
C14 H14 0.9300 . ?
C14 C16 1.341(4) . ?
C15 H15 0.9300 . ?
C15 C18 1.338(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.396(4) . ?
C17 H17 0.9300 . ?
C18 H18 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 O1 H1 109.5 . . ?
C10 O2 H2 109.5 . . ?
C5 N1 N2 114.2(2) . . ?
C2 N2 N1 112.2(2) . . ?
C6 C1 C5 119.7(2) . . ?
C6 C1 C9 119.4(2) . . ?
C9 C1 C5 120.9(2) . . ?
N2 C2 H2A 118.9 . . ?
N2 C2 C4 122.2(2) . . ?
C4 C2 H2A 118.9 . . ?
C11 C3 C4 118.9(3) . . ?
C13 C3 C4 124.1(2) . . ?
C13 C3 C11 117.0(3) . . ?
C3 C4 C2 119.9(2) . . ?
C10 C4 C2 120.6(3) . . ?
C10 C4 C3 119.4(2) . . ?
N1 C5 C1 120.5(2) . . ?
N1 C5 H5 119.7 . . ?
C1 C5 H5 119.7 . . ?
C1 C6 H6 120.2 . . ?
C7 C6 C1 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
F1 C7 C6 119.2(3) . . ?
F1 C7 C8 118.3(2) . . ?
C8 C7 C6 122.5(3) . . ?
C7 C8 H8 121.3 . . ?
C12 C8 C7 117.3(3) . . ?
C12 C8 H8 121.3 . . ?
O1 C9 C1 124.3(2) . . ?
O1 C9 C12 118.5(2) . . ?
C12 C9 C1 117.2(2) . . ?
O2 C10 C4 123.4(3) . . ?
O2 C10 C18 115.8(3) . . ?
C4 C10 C18 120.8(3) . . ?
C14 C11 C3 119.4(3) . . ?
C14 C11 C15 122.2(3) . . ?
C15 C11 C3 118.4(3) . . ?
F2 C12 C9 117.2(2) . . ?
C8 C12 F2 118.8(2) . . ?
C8 C12 C9 123.9(3) . . ?
C3 C13 H13 119.2 . . ?
C17 C13 C3 121.6(3) . . ?
C17 C13 H13 119.2 . . ?
C11 C14 H14 119.1 . . ?
C16 C14 C11 121.8(3) . . ?
C16 C14 H14 119.1 . . ?
C11 C15 H15 118.7 . . ?
C18 C15 C11 122.5(3) . . ?
C18 C15 H15 118.7 . . ?
C14 C16 H16 120.3 . . ?
C14 C16 C17 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C13 C17 C16 120.8(3) . . ?
C13 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C10 C18 H18 120.1 . . ?
C15 C18 C10 119.9(3) . . ?
C15 C18 H18 120.1 . . ?

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
F1 C7 C8 C12 179.0(2) . . . . ?
O1 C9 C12 F2 -0.5(4) . . . . ?
O1 C9 C12 C8 179.5(3) . . . . ?
O2 C10 C18 C15 178.0(3) . . . . ?
N1 N2 C2 C4 -180.0(2) . . . . ?
N2 N1 C5 C1 179.3(2) . . . . ?
N2 C2 C4 C3 177.1(2) . . . . ?
N2 C2 C4 C10 -1.3(4) . . . . ?
C1 C6 C7 F1 -180.0(2) . . . . ?
C1 C6 C7 C8 -1.4(4) . . . . ?
C1 C9 C12 F2 179.2(2) . . . . ?
C1 C9 C12 C8 -0.8(4) . . . . ?
C2 C4 C10 O2 -1.0(4) . . . . ?
C2 C4 C10 C18 178.3(2) . . . . ?
C3 C4 C10 O2 -179.4(2) . . . . ?
C3 C4 C10 C18 -0.1(4) . . . . ?
C3 C11 C14 C16 0.0(4) . . . . ?
C3 C11 C15 C18 1.1(4) . . . . ?
C3 C13 C17 C16 -0.6(5) . . . . ?
C4 C3 C11 C14 178.2(2) . . . . ?
C4 C3 C11 C15 -2.4(4) . . . . ?
C4 C3 C13 C17 -177.8(3) . . . . ?
C4 C10 C18 C15 -1.3(4) . . . . ?
C5 N1 N2 C2 -177.9(2) . . . . ?
C5 C1 C6 C7 -179.9(2) . . . . ?
C5 C1 C9 O1 0.7(4) . . . . ?
C5 C1 C9 C12 -179.0(2) . . . . ?
C6 C1 C5 N1 180.0(2) . . . . ?
C6 C1 C9 O1 179.5(2) . . . . ?
C6 C1 C9 C12 -0.2(4) . . . . ?
C6 C7 C8 C12 0.5(4) . . . . ?
C7 C8 C12 F2 -179.3(2) . . . . ?
C7 C8 C12 C9 0.7(4) . . . . ?
C9 C1 C5 N1 -1.2(4) . . . . ?
C9 C1 C6 C7 1.3(4) . . . . ?
C11 C3 C4 C2 -176.4(2) . . . . ?
C11 C3 C4 C10 2.0(3) . . . . ?
C11 C3 C13 C17 1.0(4) . . . . ?
C11 C14 C16 C17 0.5(5) . . . . ?
C11 C15 C18 C10 0.8(5) . . . . ?
C13 C3 C4 C2 2.4(4) . . . . ?
C13 C3 C4 C10 -179.2(2) . . . . ?
C13 C3 C11 C14 -0.8(4) . . . . ?
C13 C3 C11 C15 178.7(2) . . . . ?
C14 C11 C15 C18 -179.5(3) . . . . ?
C14 C16 C17 C13 -0.2(5) . . . . ?
C15 C11 C14 C16 -179.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform : n-Hexane'
_exptl_crystal_preparation       Luminescent
