# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_exter123_0m
_database_code_depnum_ccdc_archive 'CCDC 2346438'
loop_
_audit_author_name
_audit_author_address
'Ravi Kumar Kottalanka'
;Vignans Foundation for Science Technology and Research 
India
;
_audit_update_record             
;
2024-04-08 deposited with the CCDC.	2025-03-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_exter123_0m         
;
PROBLEM: Hirshfeld Test Diff for    F1       --C18      .       15.4 s.u.
RESPONSE: Due to disorder in CF3 group
;
_vrf_PLAT234_exter123_0m         
;
PROBLEM: Large Hirshfeld Difference F2       --C18      .       0.28 Ang.
RESPONSE: Due to disorder in CF3 group
;
_vrf_PLAT340_exter123_0m         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01067 Ang.
RESPONSE: Due to disorder 
;
_vrf_PLAT368_exter123_0m         
;
PROBLEM: Short  C(sp2)-C(sp2) Bond  C20      - C21      .       1.09 Ang.
RESPONSE: Due to disorder 
;
# Added during the CSD deposition process: Monday 08 April 2024 07:01 AM
# end Validation Reply Form

_audit_creation_date             2023-10-31
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 F3 N5 O2'
_chemical_formula_sum            'C22 H14 F3 N5 O2'
_chemical_formula_weight         437.38
_chemical_absolute_configuration syn
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.798(3)
_cell_length_b                   11.682(4)
_cell_length_c                   16.946(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2137.7(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.00
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1396 before and 0.0722 after correction.
The Ratio of minimum to maximum transmission is 0.8725.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.194
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48768
_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         25.349
_diffrn_reflns_theta_min         2.117
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_standards_number         0
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3176
_reflns_number_total             3900
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.694
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Flack x determined using 1174 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0882
_refine_ls_restrained_S_all      1.234
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2741
_refine_ls_wR_factor_ref         0.2903
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C21) = Uanis(C20) = Uanis(C19)
Uanis(F2) = Uanis(F1)
3.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C3(H3), C14(H14), C6(H6), C5(H5), C4(H4), C20(H20)
3.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B), C21(H21A,H21B)
;
_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
O1 O -0.7710(4) -0.3176(4) -0.4587(3) 0.0673(14) Uani 1 1 d . . . . .
N1 N -0.5996(4) -0.4212(5) -0.4210(3) 0.0496(12) Uani 1 1 d . . . . .
N5 N -0.3729(6) -0.5310(5) -0.2116(3) 0.0555(13) Uani 1 1 d . . . . .
N2 N -0.5721(4) -0.5154(4) -0.3712(3) 0.0497(12) Uani 1 1 d . . . . .
O2 O -0.4966(5) -0.3731(5) -0.2290(3) 0.0758(15) Uani 1 1 d . . . . .
C12 C -0.3269(5) -0.6195(5) -0.2595(3) 0.0446(12) Uani 1 1 d . . . . .
C2 C -0.7764(5) -0.4782(5) -0.3652(3) 0.0467(13) Uani 1 1 d . . . . .
C1 C -0.7254(5) -0.3947(6) -0.4195(3) 0.0490(13) Uani 1 1 d . . . . .
C17 C -0.3714(5) -0.6091(5) -0.3360(3) 0.0458(13) Uani 1 1 d . . . . .
N3 N -0.4977(5) -0.2796(6) -0.4896(3) 0.0645(16) Uani 1 1 d . . . . .
H3A H -0.566651 -0.260718 -0.511409 0.077 Uiso 1 1 calc R . . . .
H3B H -0.431010 -0.242951 -0.501110 0.077 Uiso 1 1 calc R . . . .
C7 C -0.6823(5) -0.5429(5) -0.3336(4) 0.0461(13) Uani 1 1 d . . . . .
C8 C -0.4943(5) -0.3632(5) -0.4393(4) 0.0482(14) Uani 1 1 d . . . . .
N4 N -0.1709(6) -0.3553(7) -0.4036(4) 0.0784(19) Uani 1 1 d . . . . .
C22 C -0.2753(6) -0.3805(6) -0.4013(4) 0.0553(15) Uani 1 1 d . . . . .
C9 C -0.3984(5) -0.4107(5) -0.3966(4) 0.0494(14) Uani 1 1 d . . . . .
C16 C -0.3417(7) -0.6860(6) -0.3916(4) 0.0588(16) Uani 1 1 d . . . . .
H16 H -0.371388 -0.677032 -0.442770 0.071 Uiso 1 1 calc R . . . .
C13 C -0.2487(6) -0.7089(6) -0.2397(4) 0.0584(16) Uani 1 1 d . . . . .
H13 H -0.216397 -0.715737 -0.189024 0.070 Uiso 1 1 calc R . . . .
C11 C -0.4455(6) -0.4570(5) -0.2537(4) 0.0531(15) Uani 1 1 d . . . . .
C3 C -0.9010(6) -0.4967(7) -0.3423(5) 0.0640(17) Uani 1 1 d . . . . .
H3 H -0.965787 -0.455968 -0.365089 0.077 Uiso 1 1 calc R . . . .
C10 C -0.4464(5) -0.5000(5) -0.3404(3) 0.0425(12) Uani 1 1 d . . . . .
C14 C -0.2206(7) -0.7862(6) -0.2968(5) 0.0665(19) Uani 1 1 d . . . . .
H14 H -0.168304 -0.846718 -0.284142 0.080 Uiso 1 1 calc R . . . .
C15 C -0.2663(7) -0.7794(7) -0.3732(5) 0.0711(19) Uani 1 1 d . . . . .
C6 C -0.7026(7) -0.6250(6) -0.2777(5) 0.0653(18) Uani 1 1 d . . . . .
H6 H -0.638854 -0.670191 -0.257968 0.078 Uiso 1 1 calc R . . . .
C5 C -0.8242(8) -0.6368(8) -0.2520(6) 0.083(2) Uani 1 1 d . . . . .
H5 H -0.841018 -0.686928 -0.210690 0.100 Uiso 1 1 calc R . . . .
C19 C -0.3504(14) -0.5183(13) -0.1267(7) 0.122(3) Uani 1 1 d . . . . .
H19A H -0.355049 -0.592976 -0.101880 0.146 Uiso 1 1 calc R . . . .
H19B H -0.415110 -0.470880 -0.104092 0.146 Uiso 1 1 calc R . . . .
C4 C -0.9212(7) -0.5766(7) -0.2858(6) 0.077(2) Uani 1 1 d . . . . .
H4 H -1.001807 -0.591214 -0.269333 0.092 Uiso 1 1 calc R . . . .
F3 F -0.1793(17) -0.9511(9) -0.4086(7) 0.256(9) Uani 1 1 d . . . . .
C18 C -0.2381(16) -0.8599(10) -0.4264(7) 0.126(5) Uani 1 1 d . . . . .
F2 F -0.176(2) -0.8295(14) -0.4876(10) 0.299(8) Uani 1 1 d . . . . .
F1 F -0.325(2) -0.9043(12) -0.4674(11) 0.299(8) Uani 1 1 d . . . . .
C20 C -0.2262(13) -0.4653(14) -0.1084(8) 0.122(3) Uani 1 1 d . . . . .
H20 H -0.203155 -0.469076 -0.055562 0.146 Uiso 1 1 calc R . . . .
C21 C -0.1586(14) -0.4233(13) -0.1468(7) 0.122(3) Uani 1 1 d . . . . .
H21A H -0.174545 -0.416064 -0.200517 0.146 Uiso 1 1 calc R . . . .
H21B H -0.085246 -0.394887 -0.125789 0.146 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
O1 C1 1.224(8) . ?
N1 N2 1.418(7) . ?
N1 C1 1.393(8) . ?
N1 C8 1.360(8) . ?
N5 C12 1.405(8) . ?
N5 C11 1.367(9) . ?
N5 C19 1.468(13) . ?
N2 C7 1.387(8) . ?
N2 C10 1.466(7) . ?
O2 C11 1.200(8) . ?
C12 C17 1.389(9) . ?
C12 C13 1.384(9) . ?
C2 C1 1.450(9) . ?
C2 C7 1.375(8) . ?
C2 C3 1.416(9) . ?
C17 C16 1.341(9) . ?
C17 C10 1.512(8) . ?
N3 C8 1.296(8) . ?
C7 C6 1.366(9) . ?
C8 C9 1.380(8) . ?
N4 C22 1.167(9) . ?
C22 C9 1.377(9) . ?
C9 C10 1.505(8) . ?
C16 C15 1.396(10) . ?
C13 C14 1.359(11) . ?
C11 C10 1.553(9) . ?
C3 C4 1.355(12) . ?
C14 C15 1.388(12) . ?
C15 C18 1.337(13) . ?
C6 C5 1.390(12) . ?
C5 C4 1.386(13) . ?
C19 C20 1.509(19) . ?
F3 C18 1.277(15) . ?
C18 F2 1.28(2) . ?
C18 F1 1.28(3) . ?
C20 C21 1.094(16) . ?

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 N2 111.4(5) . . ?
C8 N1 N2 110.4(4) . . ?
C8 N1 C1 135.1(5) . . ?
C12 N5 C19 125.6(8) . . ?
C11 N5 C12 111.6(5) . . ?
C11 N5 C19 122.9(8) . . ?
N1 N2 C10 108.1(4) . . ?
C7 N2 N1 105.9(4) . . ?
C7 N2 C10 131.2(5) . . ?
C17 C12 N5 110.6(5) . . ?
C13 C12 N5 129.2(6) . . ?
C13 C12 C17 120.2(6) . . ?
C7 C2 C1 109.6(5) . . ?
C7 C2 C3 120.8(6) . . ?
C3 C2 C1 129.6(6) . . ?
O1 C1 N1 123.1(6) . . ?
O1 C1 C2 133.4(6) . . ?
N1 C1 C2 103.5(5) . . ?
C12 C17 C10 107.8(5) . . ?
C16 C17 C12 121.0(5) . . ?
C16 C17 C10 131.1(5) . . ?
C2 C7 N2 109.1(5) . . ?
C6 C7 N2 128.2(6) . . ?
C6 C7 C2 122.5(6) . . ?
N1 C8 C9 107.9(5) . . ?
N3 C8 N1 120.1(5) . . ?
N3 C8 C9 132.0(6) . . ?
N4 C22 C9 178.6(7) . . ?
C8 C9 C10 110.6(5) . . ?
C22 C9 C8 126.2(6) . . ?
C22 C9 C10 123.1(5) . . ?
C17 C16 C15 120.4(6) . . ?
C14 C13 C12 117.7(6) . . ?
N5 C11 C10 107.0(5) . . ?
O2 C11 N5 126.7(6) . . ?
O2 C11 C10 126.2(6) . . ?
C4 C3 C2 116.8(7) . . ?
N2 C10 C17 114.2(5) . . ?
N2 C10 C9 100.3(4) . . ?
N2 C10 C11 112.5(4) . . ?
C17 C10 C11 102.9(4) . . ?
C9 C10 C17 115.6(5) . . ?
C9 C10 C11 111.8(5) . . ?
C13 C14 C15 123.2(6) . . ?
C14 C15 C16 117.4(7) . . ?
C18 C15 C16 122.1(9) . . ?
C18 C15 C14 120.5(9) . . ?
C7 C6 C5 116.1(7) . . ?
C4 C5 C6 122.2(7) . . ?
N5 C19 C20 113.0(11) . . ?
C3 C4 C5 121.4(7) . . ?
F3 C18 C15 122.8(12) . . ?
F3 C18 F2 99.3(15) . . ?
F2 C18 C15 117.9(13) . . ?
F1 C18 C15 119.1(14) . . ?
F1 C18 F3 98.8(14) . . ?
F1 C18 F2 93.2(15) . . ?
C21 C20 C19 130.8(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
