# Supplementary Information (SI) for ChemComm.
# 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. 
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data_nsetmf_0m
_database_code_depnum_ccdc_archive 'CCDC 2517708'
loop_
_audit_author_name
_audit_author_address
'Bindu Sagar Das'
;Indian Institute of technology Delhi 
India
;
_audit_update_record             
;
2025-12-20 deposited with the CCDC.	2026-05-19 downloaded from the CCDC.
;
_audit_creation_date             2025-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 F N O'
_chemical_formula_sum            'C18 H18 F N O'
_chemical_formula_weight         283.33
_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/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                   8.8231(3)
_cell_length_b                   18.1789(6)
_cell_length_c                   9.0840(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.6910(10)
_cell_angle_gamma                90
_cell_volume                     1443.91(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      28.270
_cell_measurement_theta_min      2.329
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0845 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.9527.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            39874
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.306
_diffrn_reflns_theta_min         2.241
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3238
_reflns_number_total             3579
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.067
_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)+(0.0721P)²+0.6744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1357
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C11, F1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C6(H6), C7(H7), C18(H18), C15(H15), C17(H17), C5(H5),
 C16(H16)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O -0.01076(11) 0.62074(6) 0.44885(11) 0.0270(2) Uani 1 1 d . . . . .
N1 N 0.25194(12) 0.62795(6) 0.48091(11) 0.0198(2) Uani 1 1 d . . . . .
C1 C 0.10974(14) 0.63387(7) 0.40195(13) 0.0199(2) Uani 1 1 d . . . . .
C4 C 0.36570(14) 0.64871(6) 0.39399(13) 0.0186(2) Uani 1 1 d . . . . .
C13 C 0.14296(14) 0.53019(7) 0.14101(13) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.29739(14) 0.67042(6) 0.25280(13) 0.0187(2) Uani 1 1 d . . . . .
C2 C 0.12684(14) 0.66075(7) 0.24434(13) 0.0190(2) Uani 1 1 d . . . . .
C8 C 0.38727(15) 0.69484(7) 0.14943(14) 0.0230(3) Uani 1 1 d . . . . .
H8 H 0.342217 0.710234 0.053537 0.028 Uiso 1 1 calc R U . . .
C14 C 0.11001(15) 0.47662(7) 0.24191(14) 0.0236(3) Uani 1 1 d . . . . .
H14 H 0.034889 0.486221 0.305214 0.028 Uiso 1 1 calc R U . . .
C6 C 0.61208(15) 0.67376(8) 0.32850(16) 0.0268(3) Uani 1 1 d . . . . .
H6 H 0.720206 0.674715 0.352661 0.032 Uiso 1 1 calc R U . . .
C7 C 0.54632(15) 0.69645(7) 0.18891(16) 0.0262(3) Uani 1 1 d . . . . .
H7 H 0.609690 0.713293 0.119170 0.031 Uiso 1 1 calc R U . . .
C18 C 0.25478(15) 0.51499(7) 0.05051(14) 0.0249(3) Uani 1 1 d . . . . .
H18 H 0.279552 0.551061 -0.018086 0.030 Uiso 1 1 calc R U . . .
C15 C 0.18568(16) 0.40928(8) 0.25114(15) 0.0261(3) Uani 1 1 d . . . . .
H15 H 0.161901 0.373275 0.320310 0.031 Uiso 1 1 calc R U . . .
C11 C 0.03822(16) 0.73211(7) 0.21506(15) 0.0255(3) Uani 1 1 d . U . . .
C17 C 0.33063(16) 0.44769(8) 0.05928(16) 0.0277(3) Uani 1 1 d . . . . .
H17 H 0.406318 0.438046 -0.003387 0.033 Uiso 1 1 calc R U . . .
C12 C 0.05942(15) 0.60282(7) 0.12857(14) 0.0230(3) Uani 1 1 d . . . . .
H12A H -0.049015 0.594152 0.140614 0.028 Uiso 1 1 calc R U . . .
H12B H 0.061991 0.622998 0.027706 0.028 Uiso 1 1 calc R U . . .
C5 C 0.52251(15) 0.64954(7) 0.43421(15) 0.0231(3) Uani 1 1 d . . . . .
H5 H 0.567459 0.634203 0.530175 0.028 Uiso 1 1 calc R U . . .
C9 C 0.28075(15) 0.60031(7) 0.63278(13) 0.0233(3) Uani 1 1 d . . . . .
H9A H 0.187422 0.606557 0.681074 0.028 Uiso 1 1 calc R U . . .
H9B H 0.363549 0.629539 0.689413 0.028 Uiso 1 1 calc R U . . .
C16 C 0.29587(16) 0.39464(8) 0.15943(15) 0.0274(3) Uani 1 1 d . . . . .
H16 H 0.347181 0.348576 0.165174 0.033 Uiso 1 1 calc R U . . .
C10 C 0.32622(18) 0.51952(8) 0.63757(16) 0.0305(3) Uani 1 1 d . . . . .
H10A H 0.245974 0.490620 0.578888 0.046 Uiso 1 1 calc R U . . .
H10B H 0.339427 0.502271 0.740705 0.046 Uiso 1 1 calc R U . . .
H10C H 0.422541 0.513629 0.596205 0.046 Uiso 1 1 calc R U . . .
H11A H 0.0541(19) 0.7529(9) 0.1205(19) 0.023(4) Uiso 1 1 d . . . . .
H11B H -0.070(2) 0.7242(10) 0.2200(19) 0.030(4) Uiso 1 1 d . . . . .
F1 F 0.09025(12) 0.78276(5) 0.32596(11) 0.0413(3) Uani 1 1 d . U . A 1


_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
O1 C1 1.2207(16) . ?
N1 C1 1.3636(16) . ?
N1 C4 1.4090(15) . ?
N1 C9 1.4583(15) . ?
C1 C2 1.5392(17) . ?
C4 C3 1.3989(17) . ?
C4 C5 1.3830(17) . ?
C13 C14 1.3944(18) . ?
C13 C18 1.3938(18) . ?
C13 C12 1.5090(18) . ?
C3 C2 1.5068(16) . ?
C3 C8 1.3809(17) . ?
C2 C11 1.5197(17) . ?
C2 C12 1.5496(17) . ?
C8 H8 0.9500 . ?
C8 C7 1.4014(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3915(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.385(2) . ?
C6 C5 1.3942(19) . ?
C7 H7 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.3917(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(2) . ?
C11 H11A 0.965(17) . ?
C11 H11B 0.970(18) . ?
C11 F1 1.3964(17) . ?
C17 H17 0.9500 . ?
C17 C16 1.388(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C5 H5 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5216(19) . ?
C16 H16 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
C1 N1 C4 111.00(10) . . ?
C1 N1 C9 123.81(11) . . ?
C4 N1 C9 125.13(10) . . ?
O1 C1 N1 125.74(12) . . ?
O1 C1 C2 125.81(11) . . ?
N1 C1 C2 108.45(10) . . ?
C3 C4 N1 109.73(10) . . ?
C5 C4 N1 128.12(11) . . ?
C5 C4 C3 122.15(11) . . ?
C14 C13 C12 121.17(12) . . ?
C18 C13 C14 118.39(12) . . ?
C18 C13 C12 120.43(11) . . ?
C4 C3 C2 108.58(10) . . ?
C8 C3 C4 119.87(11) . . ?
C8 C3 C2 131.55(11) . . ?
C1 C2 C12 109.82(10) . . ?
C3 C2 C1 102.19(9) . . ?
C3 C2 C11 113.35(10) . . ?
C3 C2 C12 113.82(10) . . ?
C11 C2 C1 108.76(10) . . ?
C11 C2 C12 108.63(10) . . ?
C3 C8 H8 120.7 . . ?
C3 C8 C7 118.63(12) . . ?
C7 C8 H8 120.7 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.89(12) . . ?
C15 C14 H14 119.6 . . ?
C7 C6 H6 119.4 . . ?
C7 C6 C5 121.20(12) . . ?
C5 C6 H6 119.4 . . ?
C8 C7 H7 119.6 . . ?
C6 C7 C8 120.70(12) . . ?
C6 C7 H7 119.6 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.89(12) . . ?
C17 C18 H18 119.6 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.10(12) . . ?
C16 C15 H15 120.0 . . ?
C2 C11 H11A 110.9(10) . . ?
C2 C11 H11B 110.5(11) . . ?
H11A C11 H11B 111.1(15) . . ?
F1 C11 C2 108.96(11) . . ?
F1 C11 H11A 108.1(10) . . ?
F1 C11 H11B 107.1(11) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.11(13) . . ?
C16 C17 H17 119.9 . . ?
C13 C12 C2 113.85(10) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C2 C12 H12A 108.8 . . ?
C2 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C4 C5 C6 117.44(12) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
N1 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
N1 C9 C10 111.81(10) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.61(13) . . ?
C17 C16 H16 120.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
O1 C1 C2 C3 177.66(12) . . . . ?
O1 C1 C2 C11 57.56(16) . . . . ?
O1 C1 C2 C12 -61.20(16) . . . . ?
N1 C1 C2 C3 -1.70(13) . . . . ?
N1 C1 C2 C11 -121.80(11) . . . . ?
N1 C1 C2 C12 119.44(11) . . . . ?
N1 C4 C3 C2 -2.10(13) . . . . ?
N1 C4 C3 C8 178.45(11) . . . . ?
N1 C4 C5 C6 -178.89(12) . . . . ?
C1 N1 C4 C3 0.98(14) . . . . ?
C1 N1 C4 C5 -179.46(12) . . . . ?
C1 N1 C9 C10 97.82(15) . . . . ?
C1 C2 C11 F1 55.86(13) . . . . ?
C1 C2 C12 C13 -64.03(13) . . . . ?
C4 N1 C1 O1 -178.82(12) . . . . ?
C4 N1 C1 C2 0.54(14) . . . . ?
C4 N1 C9 C10 -79.06(15) . . . . ?
C4 C3 C2 C1 2.27(12) . . . . ?
C4 C3 C2 C11 119.11(11) . . . . ?
C4 C3 C2 C12 -116.07(11) . . . . ?
C4 C3 C8 C7 0.68(18) . . . . ?
C13 C14 C15 C16 0.11(19) . . . . ?
C13 C18 C17 C16 -0.2(2) . . . . ?
C3 C4 C5 C6 0.62(19) . . . . ?
C3 C2 C11 F1 -57.06(14) . . . . ?
C3 C2 C12 C13 49.83(14) . . . . ?
C3 C8 C7 C6 0.2(2) . . . . ?
C2 C3 C8 C7 -178.62(12) . . . . ?
C8 C3 C2 C1 -178.37(13) . . . . ?
C8 C3 C2 C11 -61.53(18) . . . . ?
C8 C3 C2 C12 63.29(17) . . . . ?
C14 C13 C18 C17 0.71(19) . . . . ?
C14 C13 C12 C2 83.69(15) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C7 C6 C5 C4 0.3(2) . . . . ?
C18 C13 C14 C15 -0.65(19) . . . . ?
C18 C13 C12 C2 -96.73(14) . . . . ?
C18 C17 C16 C15 -0.3(2) . . . . ?
C11 C2 C12 C13 177.14(11) . . . . ?
C12 C13 C14 C15 178.93(11) . . . . ?
C12 C13 C18 C17 -178.87(12) . . . . ?
C12 C2 C11 F1 175.36(10) . . . . ?
C5 C4 C3 C2 178.31(11) . . . . ?
C5 C4 C3 C8 -1.14(18) . . . . ?
C5 C6 C7 C8 -0.8(2) . . . . ?
C9 N1 C1 O1 3.9(2) . . . . ?
C9 N1 C1 C2 -176.73(11) . . . . ?
C9 N1 C4 C3 178.21(11) . . . . ?
C9 N1 C4 C5 -2.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
