# Supplementary Information (SI) for Journal of Materials Chemistry C.
# 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_mr_vg_pre_autored
_database_code_depnum_ccdc_archive 'CCDC 2388391'
loop_
_audit_author_name
_audit_author_address
'Lakshmi Vellanki'
;National Institute of Technology Karnataka
India
;
_audit_update_record             
;
2025-09-14 deposited with the CCDC.	2025-10-15 downloaded from the CCDC.
;
_audit_creation_date             2025-09-12
_audit_creation_method           
;
Olex2 1.5-ac6-020
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6966)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 F2 N2 O2'
_chemical_formula_sum            'C16 H10 F2 N2 O2'
_chemical_formula_weight         300.26
_chemical_melting_point          ?
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.1306(2)
_cell_length_b                   5.7865(2)
_cell_length_c                   17.5969(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.639(3)
_cell_angle_gamma                90
_cell_volume                     622.99(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4356
_cell_measurement_temperature    107.5(7)
_cell_measurement_theta_max      30.5020
_cell_measurement_theta_min      3.4350
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10779
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.676
_diffrn_reflns_theta_min         3.456
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      107.5(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    -80.30 139.30   1.80   10.00  72.69 -18.16  31.50    --   122
  2  ω   -122.88  22.92   1.80   10.00    --  -18.16 -59.25  20.08   81
  3  ω   -122.88  22.92   1.80   10.00    --  -18.16 -59.25-135.92   81
  4  φ   -135.92  47.68   1.80   10.00  23.19 -18.16 -59.25    --   102
  5  ω   -122.88  22.92   1.80   10.00    --  -18.16 -59.25 173.08   81
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0884407000
_diffrn_orient_matrix_UB_12      0.0516015000
_diffrn_orient_matrix_UB_13      -0.0177387000
_diffrn_orient_matrix_UB_21      0.0554008000
_diffrn_orient_matrix_UB_22      -0.1077196000
_diffrn_orient_matrix_UB_23      0.0008908000
_diffrn_orient_matrix_UB_31      -0.0501997000
_diffrn_orient_matrix_UB_32      -0.0279230000
_diffrn_orient_matrix_UB_33      -0.0362970000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1510
_reflns_number_total             1738
_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       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       
'PROGRAM:BIS V6.2.16/2021-10-22 && APEX4 2021.4-0                                '
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-020 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1738
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.066
_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)+(0.0552P)²+0.2942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1164
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 1.01939(12) 0.60130(13) 0.41956(5) 0.0214(2) Uani 1 1 d . . . . .
O1 O 0.81985(13) -0.13684(15) 0.55628(5) 0.0175(2) Uani 1 1 d . . . . .
N1 N 0.72109(16) 0.27318(17) 0.44310(6) 0.0133(2) Uani 1 1 d . . . . .
H1 H 0.861507 0.255481 0.455335 0.026(4) Uiso 1 1 calc R . . . .
C7 C 0.58796(18) 0.12253(19) 0.47351(7) 0.0119(2) Uani 1 1 d . . . . .
C1 C 0.66372(19) 0.4580(2) 0.39355(7) 0.0128(3) Uani 1 1 d . . . . .
C8 C 0.64604(18) -0.06578(19) 0.52625(7) 0.0124(3) Uani 1 1 d . . . . .
C6 C 0.82209(19) 0.6259(2) 0.38232(7) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.45870(19) 0.4838(2) 0.35550(7) 0.0163(3) Uani 1 1 d . . . . .
H2 H 0.347266 0.372678 0.361902 0.020(4) Uiso 1 1 calc R . . . .
C5 C 0.7846(2) 0.8134(2) 0.33509(7) 0.0182(3) Uani 1 1 d . . . . .
H5 H 0.896256 0.923996 0.328353 0.028(4) Uiso 1 1 calc R . . . .
C3 C 0.4185(2) 0.6735(2) 0.30807(8) 0.0207(3) Uani 1 1 d . . . . .
H3 H 0.278377 0.691384 0.282443 0.032(5) Uiso 1 1 calc R . . . .
C4 C 0.5795(2) 0.8371(2) 0.29754(8) 0.0210(3) Uani 1 1 d . . . . .
H4 H 0.549495 0.965024 0.264698 0.025(4) Uiso 1 1 calc R . . . .


_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 C6 1.3462(14) . ?
O1 C8 1.2298(14) . ?
N1 H1 0.8800 . ?
N1 C7 1.3296(15) . ?
N1 C1 1.4101(15) . ?
C7 C8 1.4606(16) . ?
C7 C8 1.4720(15) 3_656 ?
C1 C6 1.3966(16) . ?
C1 C2 1.3942(16) . ?
C6 C5 1.3773(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3914(18) . ?
C5 H5 0.9500 . ?
C5 C4 1.3894(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.3887(19) . ?
C4 H4 0.9500 . ?

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
C7 N1 H1 116.2 . . ?
C7 N1 C1 127.64(10) . . ?
C1 N1 H1 116.2 . . ?
N1 C7 C8 127.86(11) . . ?
N1 C7 C8 140.41(11) . 3_656 ?
C8 C7 C8 91.72(9) . 3_656 ?
C6 C1 N1 117.83(11) . . ?
C2 C1 N1 124.07(10) . . ?
C2 C1 C6 118.10(11) . . ?
O1 C8 C7 137.92(11) . 3_656 ?
O1 C8 C7 133.80(11) . . ?
C7 C8 C7 88.28(9) . 3_656 ?
F1 C6 C1 117.95(11) . . ?
F1 C6 C5 119.18(11) . . ?
C5 C6 C1 122.87(12) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.52(11) . . ?
C3 C2 H2 120.2 . . ?
C6 C5 H5 120.8 . . ?
C6 C5 C4 118.42(12) . . ?
C4 C5 H5 120.8 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.15(12) . . ?
C4 C3 H3 119.4 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 119.93(12) . . ?
C3 C4 H4 120.0 . . ?

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 C6 C5 C4 -179.52(10) . . . . ?
N1 C7 C8 O1 0.2(2) . . . . ?
N1 C7 C8 C7 179.55(15) . . . 3_656 ?
N1 C1 C6 F1 -0.13(16) . . . . ?
N1 C1 C6 C5 179.82(11) . . . . ?
N1 C1 C2 C3 179.68(11) . . . . ?
C7 N1 C1 C6 165.54(11) . . . . ?
C7 N1 C1 C2 -14.12(19) . . . . ?
C1 N1 C7 C8 0.9(2) . . . 3_656 ?
C1 N1 C7 C8 -178.43(11) . . . . ?
C1 C6 C5 C4 0.53(19) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C8 C7 C8 O1 -179.40(17) 3_656 . . . ?
C8 C7 C8 C7 -0.001(0) 3_656 . . 3_656 ?
C6 C1 C2 C3 0.03(18) . . . . ?
C6 C5 C4 C3 -0.07(19) . . . . ?
C2 C1 C6 F1 179.54(10) . . . . ?
C2 C1 C6 C5 -0.51(18) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.050
_oxdiff_exptl_absorpt_empirical_full_min 0.292
_exptl_crystal_preparation       Luminescent
