# Supplementary Information (SI) for ChemComm.
# 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_198
_database_code_depnum_ccdc_archive 'CCDC 2354829'
loop_
_audit_author_name
_audit_author_address
'Dr. ELIAS JESU PACKIAM D'
;INDIAN INSTITUTE OF TECHNOLOGY MADRAS
India
;
_audit_update_record             
;
2024-05-12 deposited with the CCDC.	2025-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 F3 N O2'
_chemical_formula_weight         343.30

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.4749(4)
_cell_length_b                   9.2492(5)
_cell_length_c                   11.6066(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.679(3)
_cell_angle_gamma                90
_cell_volume                     799.77(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3556
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      25.39

_exptl_crystal_description       Block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5036
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.734
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2750
_reflns_number_gt                2533
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_max     0.959
_reflns_Friedel_fraction_full    0.959

_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0339P)²+0.1728P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2750
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0792
_refine_ls_wR_factor_gt          0.0761
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C1 C 0.9509(4) 0.2893(3) 0.7675(3) 0.0467(7) Uani 1 1 d . . . . .
H1 H 0.9418 0.3587 0.7094 0.056 Uiso 1 1 calc R U . . .
C2 C 0.8346(4) 0.2928(4) 0.8547(3) 0.0570(8) Uani 1 1 d . . . . .
H2 H 0.7463 0.3637 0.8539 0.068 Uiso 1 1 calc R U . . .
C3 C 0.8488(5) 0.1931(4) 0.9415(3) 0.0615(9) Uani 1 1 d . . . . .
H3 H 0.7703 0.1960 0.9996 0.074 Uiso 1 1 calc R U . . .
C4 C 0.9787(5) 0.0886(4) 0.9429(3) 0.0562(8) Uani 1 1 d . . . . .
H4 H 0.9884 0.0211 1.0024 0.067 Uiso 1 1 calc R U . . .
C5 C 1.0946(4) 0.0828(3) 0.8574(2) 0.0446(7) Uani 1 1 d . . . . .
H5 H 1.1830 0.0119 0.8597 0.054 Uiso 1 1 calc R U . . .
C6 C 1.0808(3) 0.1821(3) 0.7673(2) 0.0367(6) Uani 1 1 d . . . . .
C7 C 1.1975(3) 0.1704(3) 0.6700(2) 0.0374(6) Uani 1 1 d . . . . .
C8 C 1.2074(3) 0.0579(3) 0.5917(2) 0.0360(6) Uani 1 1 d . . . . .
C9 C 1.4097(4) 0.2214(3) 0.5473(2) 0.0414(7) Uani 1 1 d . . . . .
H9 H 1.4998 0.2673 0.5104 0.050 Uiso 1 1 calc R U . . .
C10 C 1.3267(3) 0.2752(3) 0.6415(2) 0.0403(6) Uani 1 1 d . . . . .
C11 C 1.3728(4) 0.4078(4) 0.7003(3) 0.0536(8) Uani 1 1 d . . . . .
C12 C 1.1222(4) -0.0831(3) 0.5748(2) 0.0402(6) Uani 1 1 d . . . . .
C13 C 0.9632(3) -0.1196(3) 0.6394(2) 0.0365(6) Uani 1 1 d . . . . .
C14 C 0.8186(4) -0.0269(3) 0.6439(2) 0.0409(7) Uani 1 1 d . . . . .
H14 H 0.8142 0.0585 0.6015 0.049 Uiso 1 1 calc R U . . .
C15 C 0.6812(3) -0.0613(3) 0.7113(2) 0.0419(7) Uani 1 1 d . . . . .
H15 H 0.5834 0.0005 0.7137 0.050 Uiso 1 1 calc R U . . .
C16 C 0.6887(3) -0.1876(3) 0.7753(3) 0.0425(7) Uani 1 1 d . . . . .
C17 C 0.8288(4) -0.2831(3) 0.7677(3) 0.0476(7) Uani 1 1 d . . . . .
H17 H 0.8317 -0.3694 0.8090 0.057 Uiso 1 1 calc R U . . .
C18 C 0.9649(3) -0.2501(3) 0.6983(3) 0.0443(7) Uani 1 1 d . . . . .
H18 H 1.0578 -0.3155 0.6911 0.053 Uiso 1 1 calc R U . . .
C19 C 0.5465(4) -0.2182(4) 0.8552(3) 0.0579(8) Uani 1 1 d . . . . .
F1 F 0.5616(3) -0.3452(3) 0.9065(2) 0.0876(8) Uani 1 1 d . . . . .
F2 F 0.3824(2) -0.2174(3) 0.8013(2) 0.0830(7) Uani 1 1 d . . . . .
F3 F 0.5425(4) -0.1187(4) 0.9367(3) 0.1207(12) Uani 1 1 d . . . . .
N1 N 1.3387(3) 0.0939(3) 0.5192(2) 0.0405(6) Uani 1 1 d . . . . .
O1 O 1.4822(4) 0.4947(3) 0.6714(2) 0.0717(8) Uani 1 1 d . . . . .
O2 O 1.1848(3) -0.1729(2) 0.5121(2) 0.0596(6) Uani 1 1 d . . . . .
H11 H 1.316(4) 0.421(4) 0.775(3) 0.053(9) Uiso 1 1 d . . . . .
H1N H 1.370(4) 0.041(3) 0.466(3) 0.043(9) Uiso 1 1 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
C1 C2 1.386(4) . ?
C1 C6 1.388(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(3) . ?
C7 C8 1.387(4) . ?
C7 C10 1.425(4) . ?
C8 N1 1.385(3) . ?
C8 C12 1.458(4) . ?
C9 N1 1.323(4) . ?
C9 C10 1.392(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.432(4) . ?
C11 O1 1.213(4) . ?
C11 H11 1.00(3) . ?
C12 O2 1.222(3) . ?
C12 C13 1.494(4) . ?
C13 C14 1.384(4) . ?
C13 C18 1.387(4) . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(4) . ?
C16 C19 1.493(4) . ?
C17 C18 1.382(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 F1 1.318(4) . ?
C19 F3 1.321(4) . ?
C19 F2 1.331(4) . ?
N1 H1N 0.84(3) . ?

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
C2 C1 C6 119.9(3) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.7(2) . . ?
C1 C6 C7 120.5(2) . . ?
C5 C6 C7 120.8(2) . . ?
C8 C7 C10 106.5(2) . . ?
C8 C7 C6 128.2(2) . . ?
C10 C7 C6 125.3(2) . . ?
N1 C8 C7 107.2(2) . . ?
N1 C8 C12 117.2(2) . . ?
C7 C8 C12 135.5(2) . . ?
N1 C9 C10 108.4(2) . . ?
N1 C9 H9 125.8 . . ?
C10 C9 H9 125.8 . . ?
C9 C10 C7 107.0(2) . . ?
C9 C10 C11 125.1(3) . . ?
C7 C10 C11 127.8(2) . . ?
O1 C11 C10 125.3(3) . . ?
O1 C11 H11 120.1(19) . . ?
C10 C11 H11 114(2) . . ?
O2 C12 C8 120.3(2) . . ?
O2 C12 C13 120.3(3) . . ?
C8 C12 C13 119.4(2) . . ?
C14 C13 C18 119.7(2) . . ?
C14 C13 C12 122.3(3) . . ?
C18 C13 C12 117.9(2) . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 C19 120.1(3) . . ?
C15 C16 C19 119.6(3) . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C13 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
F1 C19 F3 107.7(3) . . ?
F1 C19 F2 105.1(3) . . ?
F3 C19 F2 105.0(3) . . ?
F1 C19 C16 114.2(3) . . ?
F3 C19 C16 111.8(3) . . ?
F2 C19 C16 112.4(3) . . ?
C9 N1 C8 110.8(2) . . ?
C9 N1 H1N 125(2) . . ?
C8 N1 H1N 125(2) . . ?

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
C6 C1 C2 C3 1.1(5) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C2 C1 C6 C5 -2.0(4) . . . . ?
C2 C1 C6 C7 175.5(3) . . . . ?
C4 C5 C6 C1 1.8(4) . . . . ?
C4 C5 C6 C7 -175.7(3) . . . . ?
C1 C6 C7 C8 -116.1(3) . . . . ?
C5 C6 C7 C8 61.3(4) . . . . ?
C1 C6 C7 C10 65.5(4) . . . . ?
C5 C6 C7 C10 -117.0(3) . . . . ?
C10 C7 C8 N1 0.2(3) . . . . ?
C6 C7 C8 N1 -178.3(3) . . . . ?
C10 C7 C8 C12 176.5(3) . . . . ?
C6 C7 C8 C12 -2.1(5) . . . . ?
N1 C9 C10 C7 0.0(3) . . . . ?
N1 C9 C10 C11 177.0(3) . . . . ?
C8 C7 C10 C9 -0.2(3) . . . . ?
C6 C7 C10 C9 178.5(3) . . . . ?
C8 C7 C10 C11 -177.0(3) . . . . ?
C6 C7 C10 C11 1.6(5) . . . . ?
C9 C10 C11 O1 4.9(5) . . . . ?
C7 C10 C11 O1 -178.8(3) . . . . ?
N1 C8 C12 O2 11.3(4) . . . . ?
C7 C8 C12 O2 -164.6(3) . . . . ?
N1 C8 C12 C13 -171.7(2) . . . . ?
C7 C8 C12 C13 12.3(5) . . . . ?
O2 C12 C13 C14 -134.6(3) . . . . ?
C8 C12 C13 C14 48.5(4) . . . . ?
O2 C12 C13 C18 46.8(4) . . . . ?
C8 C12 C13 C18 -130.1(3) . . . . ?
C18 C13 C14 C15 3.1(4) . . . . ?
C12 C13 C14 C15 -175.4(3) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C14 C15 C16 C17 -3.3(4) . . . . ?
C14 C15 C16 C19 175.2(3) . . . . ?
C15 C16 C17 C18 2.0(4) . . . . ?
C19 C16 C17 C18 -176.5(3) . . . . ?
C16 C17 C18 C13 1.9(4) . . . . ?
C14 C13 C18 C17 -4.4(4) . . . . ?
C12 C13 C18 C17 174.2(3) . . . . ?
C17 C16 C19 F1 -5.3(4) . . . . ?
C15 C16 C19 F1 176.3(3) . . . . ?
C17 C16 C19 F3 117.3(4) . . . . ?
C15 C16 C19 F3 -61.2(4) . . . . ?
C17 C16 C19 F2 -124.9(3) . . . . ?
C15 C16 C19 F2 56.7(4) . . . . ?
C10 C9 N1 C8 0.2(3) . . . . ?
C7 C8 N1 C9 -0.3(3) . . . . ?
C12 C8 N1 C9 -177.3(2) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.028



