# 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. 
# 
#######################################################################

data_ud_d
_database_code_depnum_ccdc_archive 'CCDC 2497335'
loop_
_audit_author_name
_audit_author_address
'Gogoi A.'
;Tezpur University
India
;
_audit_update_record             
;
2025-10-24 deposited with the CCDC.	2025-12-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_ud_d                
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: The crystals were of low quality. Therefore, not better data could be obtained. Additional refinement cycles do not improve the results.
;
_vrf_PLAT020_ud_d                
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.633 Report
RESPONSE: The crystals were of low quality. Therefore, better data could not be obtained. Additional refinement cycles do not improve the results.
;
# Added during the CSD deposition process: Friday 24 October 2025 08:27 AM
# end Validation Reply Form

_audit_creation_date             2025-10-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
abhijitgogoi047@gmail.com
trnath@tezu.ernet.in
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 F N'
_chemical_formula_sum            'C19 H16 F N'
_chemical_formula_weight         277.33
_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'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.44(11)
_cell_length_b                   7.72(6)
_cell_length_c                   26.4(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2943(39)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    414
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      11.29
_cell_measurement_theta_min      3.86
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3116
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1679 before and 0.1063 after correction.
The Ratio of minimum to maximum transmission is 0.4179.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             1168
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.6334
_diffrn_reflns_av_unetI/netI     0.2316
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            80177
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.784
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                989
_reflns_number_total             3004
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.018(3)
_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   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3004
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2662
_refine_ls_R_factor_gt           0.0901
_refine_ls_restrained_S_all      0.979
_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)+(0.0125P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.2323
_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.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C15(H15), C8(H8), C2(H2), C16(H16), C7(H7), C6(H6), C19(H19),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_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
F1 F -0.2495(2) 0.4047(5) 0.45239(11) 0.1317(13) Uani 1 1 d . . . . .
N1 N -0.3465(3) -0.0776(6) 0.10140(15) 0.0714(12) Uani 1 1 d . . . . .
C10 C -0.3352(3) 0.1195(6) 0.22831(17) 0.0610(13) Uani 1 1 d . . . . .
H10 H -0.291744 0.052569 0.245440 0.073 Uiso 1 1 calc R U . . .
C4 C -0.3984(3) 0.1722(6) 0.13666(18) 0.0614(13) Uani 1 1 d . . . . .
C14 C -0.3429(3) 0.2921(5) 0.30716(16) 0.0585(12) Uani 1 1 d . . . . .
C3 C -0.3527(3) 0.0740(6) 0.17575(17) 0.0578(12) Uani 1 1 d . . . . .
C11 C -0.3754(3) 0.2494(6) 0.25502(17) 0.0603(13) Uani 1 1 d . . . . .
C9 C -0.3929(3) 0.0762(7) 0.09135(19) 0.0687(14) Uani 1 1 d . . . . .
C1 C -0.3203(4) -0.2096(8) 0.06391(18) 0.1010(19) Uani 1 1 d . . . . .
H1A H -0.371260 -0.229582 0.041292 0.151 Uiso 1 1 calc R U . . .
H1B H -0.304890 -0.315470 0.081010 0.151 Uiso 1 1 calc R U . . .
H1C H -0.267704 -0.169909 0.044946 0.151 Uiso 1 1 calc R U . . .
C15 C -0.2499(4) 0.2704(6) 0.32035(19) 0.0713(14) Uani 1 1 d . . . . .
H15 H -0.208373 0.230876 0.296011 0.086 Uiso 1 1 calc R U . . .
C8 C -0.4279(4) 0.1365(8) 0.04512(19) 0.0808(16) Uani 1 1 d . . . . .
H8 H -0.423633 0.071629 0.015531 0.097 Uiso 1 1 calc R U . . .
C2 C -0.3222(3) -0.0754(6) 0.15186(19) 0.0676(13) Uani 1 1 d . . . . .
H2 H -0.289456 -0.163383 0.167929 0.081 Uiso 1 1 calc R U . . .
C13 C -0.4418(4) 0.4469(6) 0.18384(18) 0.0825(15) Uani 1 1 d . . . . .
H13A H -0.490351 0.532824 0.180173 0.099 Uiso 1 1 calc R U . . .
H13B H -0.383484 0.508525 0.186589 0.099 Uiso 1 1 calc R U . . .
C16 C -0.2176(4) 0.3062(6) 0.3689(2) 0.0828(16) Uani 1 1 d . . . . .
H16 H -0.155707 0.290116 0.377318 0.099 Uiso 1 1 calc R U . . .
C17 C -0.2805(5) 0.3665(7) 0.4042(2) 0.0899(17) Uani 1 1 d . . . . .
C5 C -0.4393(3) 0.3384(7) 0.13644(18) 0.0669(13) Uani 1 1 d . . . . .
C7 C -0.4697(4) 0.3000(9) 0.0460(2) 0.0942(18) Uani 1 1 d . . . . .
H7 H -0.494282 0.345429 0.016277 0.113 Uiso 1 1 calc R U . . .
C6 C -0.4751(3) 0.3969(7) 0.0909(2) 0.0832(16) Uani 1 1 d . . . . .
H6 H -0.503910 0.504599 0.090082 0.100 Uiso 1 1 calc R U . . .
C12 C -0.4582(4) 0.3479(6) 0.23335(17) 0.0818(16) Uani 1 1 d . . . . .
H12A H -0.479217 0.429903 0.258698 0.098 Uiso 1 1 calc R U . . .
H12B H -0.508016 0.265844 0.227805 0.098 Uiso 1 1 calc R U . . .
C19 C -0.4034(4) 0.3530(6) 0.34465(19) 0.0751(14) Uani 1 1 d . . . . .
H19 H -0.465512 0.369725 0.336758 0.090 Uiso 1 1 calc R U . . .
C18 C -0.3725(5) 0.3889(7) 0.3933(2) 0.0892(17) Uani 1 1 d . . . . .
H18 H -0.413537 0.427355 0.417993 0.107 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 C17 1.380(10) . ?
N1 C9 1.389(10) . ?
N1 C1 1.470(9) . ?
N1 C2 1.378(11) . ?
C10 H10 0.9300 . ?
C10 C3 1.454(12) . ?
C10 C11 1.357(9) . ?
C4 C3 1.440(9) . ?
C4 C9 1.409(10) . ?
C4 C5 1.413(11) . ?
C14 C11 1.491(11) . ?
C14 C15 1.398(11) . ?
C14 C19 1.401(9) . ?
C3 C2 1.386(9) . ?
C11 C12 1.527(10) . ?
C9 C8 1.401(10) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C16 1.391(11) . ?
C8 H8 0.9300 . ?
C8 C7 1.399(11) . ?
C2 H2 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C5 1.506(10) . ?
C13 C12 1.532(11) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(10) . ?
C17 C18 1.371(12) . ?
C5 C6 1.383(10) . ?
C7 H7 0.9300 . ?
C7 C6 1.405(11) . ?
C6 H6 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C19 H19 0.9300 . ?
C19 C18 1.387(11) . ?
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 N1 C1 126.0(6) . . ?
C2 N1 C9 107.3(4) . . ?
C2 N1 C1 126.5(5) . . ?
C3 C10 H10 116.6 . . ?
C11 C10 H10 116.6 . . ?
C11 C10 C3 126.9(5) . . ?
C9 C4 C3 107.8(7) . . ?
C9 C4 C5 119.8(5) . . ?
C5 C4 C3 132.3(5) . . ?
C15 C14 C11 120.4(4) . . ?
C15 C14 C19 117.6(6) . . ?
C19 C14 C11 122.0(6) . . ?
C4 C3 C10 129.5(6) . . ?
C2 C3 C10 125.5(4) . . ?
C2 C3 C4 104.9(6) . . ?
C10 C11 C14 120.5(5) . . ?
C10 C11 C12 120.6(6) . . ?
C14 C11 C12 118.8(5) . . ?
N1 C9 C4 108.3(6) . . ?
N1 C9 C8 128.7(5) . . ?
C8 C9 C4 123.0(7) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.8(5) . . ?
C16 C15 H15 119.1 . . ?
C9 C8 H8 121.9 . . ?
C7 C8 C9 116.2(5) . . ?
C7 C8 H8 121.9 . . ?
N1 C2 C3 111.7(5) . . ?
N1 C2 H2 124.2 . . ?
C3 C2 H2 124.2 . . ?
H13A C13 H13B 107.4 . . ?
C5 C13 H13A 108.3 . . ?
C5 C13 H13B 108.3 . . ?
C5 C13 C12 115.8(7) . . ?
C12 C13 H13A 108.3 . . ?
C12 C13 H13B 108.3 . . ?
C15 C16 H16 121.0 . . ?
C17 C16 C15 118.0(7) . . ?
C17 C16 H16 121.0 . . ?
F1 C17 C16 118.7(8) . . ?
C18 C17 F1 118.8(6) . . ?
C18 C17 C16 122.4(6) . . ?
C4 C5 C13 120.8(5) . . ?
C6 C5 C4 117.1(5) . . ?
C6 C5 C13 122.1(7) . . ?
C8 C7 H7 119.4 . . ?
C8 C7 C6 121.2(5) . . ?
C6 C7 H7 119.4 . . ?
C5 C6 C7 122.6(7) . . ?
C5 C6 H6 118.7 . . ?
C7 C6 H6 118.7 . . ?
C11 C12 C13 116.6(5) . . ?
C11 C12 H12A 108.2 . . ?
C11 C12 H12B 108.2 . . ?
C13 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
H12A C12 H12B 107.3 . . ?
C14 C19 H19 119.3 . . ?
C18 C19 C14 121.4(7) . . ?
C18 C19 H19 119.3 . . ?
C17 C18 C19 118.8(5) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?

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 C17 C18 C19 179.0(4) . . . . ?
N1 C9 C8 C7 -178.3(5) . . . . ?
C10 C3 C2 N1 -177.3(4) . . . . ?
C10 C11 C12 C13 -61.4(7) . . . . ?
C4 C3 C2 N1 -0.7(5) . . . . ?
C4 C9 C8 C7 -0.1(7) . . . . ?
C4 C5 C6 C7 -1.7(7) . . . . ?
C14 C11 C12 C13 121.8(6) . . . . ?
C14 C15 C16 C17 -0.7(7) . . . . ?
C14 C19 C18 C17 1.1(8) . . . . ?
C3 C10 C11 C14 -173.4(4) . . . . ?
C3 C10 C11 C12 9.8(7) . . . . ?
C3 C4 C9 N1 0.6(5) . . . . ?
C3 C4 C9 C8 -177.9(4) . . . . ?
C3 C4 C5 C13 -1.1(7) . . . . ?
C3 C4 C5 C6 177.8(4) . . . . ?
C11 C10 C3 C4 15.4(7) . . . . ?
C11 C10 C3 C2 -168.8(4) . . . . ?
C11 C14 C15 C16 -178.9(4) . . . . ?
C11 C14 C19 C18 178.7(4) . . . . ?
C9 N1 C2 C3 1.1(5) . . . . ?
C9 C4 C3 C10 176.5(4) . . . . ?
C9 C4 C3 C2 0.0(5) . . . . ?
C9 C4 C5 C13 -177.0(4) . . . . ?
C9 C4 C5 C6 1.9(6) . . . . ?
C9 C8 C7 C6 0.4(7) . . . . ?
C1 N1 C9 C4 -175.6(4) . . . . ?
C1 N1 C9 C8 2.8(7) . . . . ?
C1 N1 C2 C3 175.6(4) . . . . ?
C15 C14 C11 C10 32.3(6) . . . . ?
C15 C14 C11 C12 -151.0(5) . . . . ?
C15 C14 C19 C18 -0.7(7) . . . . ?
C15 C16 C17 F1 -179.2(4) . . . . ?
C15 C16 C17 C18 1.1(8) . . . . ?
C8 C7 C6 C5 0.6(8) . . . . ?
C2 N1 C9 C4 -1.0(5) . . . . ?
C2 N1 C9 C8 177.4(4) . . . . ?
C13 C5 C6 C7 177.2(5) . . . . ?
C16 C17 C18 C19 -1.4(8) . . . . ?
C5 C4 C3 C10 0.2(8) . . . . ?
C5 C4 C3 C2 -176.3(5) . . . . ?
C5 C4 C9 N1 177.4(4) . . . . ?
C5 C4 C9 C8 -1.1(7) . . . . ?
C5 C13 C12 C11 77.2(6) . . . . ?
C12 C13 C5 C4 -37.5(7) . . . . ?
C12 C13 C5 C6 143.7(6) . . . . ?
C19 C14 C11 C10 -147.1(5) . . . . ?
C19 C14 C11 C12 29.7(6) . . . . ?
C19 C14 C15 C16 0.5(7) . . . . ?

_olex2_submission_original_sample_id UD_381
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate/ hexane'
