# 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_cu_sj_pF_chiral_crystal_a
_database_code_depnum_ccdc_archive 'CCDC 2538476'
loop_
_audit_author_name
_audit_author_address
'Dr Rajesh G Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2026-03-17 deposited with the CCDC.	2026-06-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_cu_sj_pF_chiral_crystal_a 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0125 Ang.  
RESPONSE: This is due to the poor diffraction data. The crystals were fragile.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 F N O4'
_chemical_formula_sum            'C21 H20 F N O4'
_chemical_formula_weight         369.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   13.1028(12)
_cell_length_b                   5.4590(5)
_cell_length_c                   13.4341(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.372(5)
_cell_angle_gamma                90
_cell_volume                     917.09(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7660
_cell_measurement_theta_min      3.442
_cell_measurement_theta_max      65.9295

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.826
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.866
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1025
_exptl_absorpt_correction_T_max  0.2259
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            16869
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.447
_diffrn_reflns_theta_max         72.064
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_point_group_measured_fraction_full 0.861
_reflns_number_total             2977
_reflns_number_gt                1852
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.556
_reflns_Friedel_fraction_max     0.663
_reflns_Friedel_fraction_full    0.718

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL, Mercury 2020.20'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0656P)²+0.9647P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary   'difference Fourier'
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.2157
_refine_ls_wR_factor_gt          0.1722
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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
F1 F 0.0465(4) 0.3877(15) -0.0047(5) 0.134(2) Uani 1 1 d . . . . .
O1 O 0.7148(5) 0.1613(11) 0.3177(4) 0.0886(17) Uani 1 1 d . . . . .
O2 O 0.6108(4) 0.8425(12) 0.4560(4) 0.0906(17) Uani 1 1 d . . . . .
O3 O 0.5990(6) 0.3327(15) 0.0221(5) 0.115(2) Uani 1 1 d . . . . .
O4 O 0.6415(5) 0.5998(12) 0.1548(4) 0.0865(17) Uani 1 1 d . . . . .
N1 N 0.6847(5) 0.4948(12) 0.4075(4) 0.0691(16) Uani 1 1 d . . . . .
C1 C 0.5110(5) 0.6088(16) 0.3044(6) 0.071(2) Uani 1 1 d . . . . .
H1 H 0.509742 0.724545 0.248281 0.086 Uiso 1 1 calc R U . . .
C2 C 0.5393(6) 0.3517(16) 0.2723(5) 0.0703(19) Uani 1 1 d . . . . .
H2 H 0.498894 0.233361 0.300447 0.084 Uiso 1 1 calc R U . . .
C3 C 0.6558(6) 0.3166(16) 0.3320(5) 0.070(2) Uani 1 1 d . . . . .
C4 C 0.6042(6) 0.6697(16) 0.3976(6) 0.075(2) Uani 1 1 d . . . . .
C5 C 0.4054(6) 0.6290(19) 0.3305(6) 0.079(2) Uani 1 1 d . . . . .
H5A H 0.408165 0.520748 0.388543 0.095 Uiso 1 1 calc R U . . .
H5B H 0.397886 0.795142 0.352939 0.095 Uiso 1 1 calc R U . . .
C6 C 0.3082(6) 0.5658(16) 0.2410(6) 0.073(2) Uani 1 1 d . . . . .
C7 C 0.2464(7) 0.365(2) 0.2461(7) 0.089(2) Uani 1 1 d . . . . .
H7 H 0.265017 0.270078 0.306242 0.107 Uiso 1 1 calc R U . . .
C8 C 0.1572(7) 0.300(2) 0.1645(8) 0.100(3) Uani 1 1 d . . . . .
H8 H 0.115615 0.164931 0.168856 0.121 Uiso 1 1 calc R U . . .
C9 C 0.1337(7) 0.443(2) 0.0785(8) 0.094(3) Uani 1 1 d . . . . .
C10 C 0.1898(7) 0.642(2) 0.0699(7) 0.097(3) Uani 1 1 d . . . . .
H10 H 0.169427 0.737881 0.010067 0.117 Uiso 1 1 calc R U . . .
C11 C 0.2795(7) 0.7027(19) 0.1523(7) 0.091(3) Uani 1 1 d . . . . .
H11 H 0.320234 0.838539 0.146645 0.109 Uiso 1 1 calc R U . . .
C12 C 0.5135(6) 0.2983(16) 0.1563(5) 0.078(2) Uani 1 1 d . . . . .
H12A H 0.513060 0.122079 0.146872 0.094 Uiso 1 1 calc R U . . .
H12B H 0.441841 0.357279 0.121698 0.094 Uiso 1 1 calc R U . . .
C13 C 0.5882(7) 0.4085(18) 0.1030(7) 0.081(2) Uani 1 1 d . . . . .
C14 C 0.7248(8) 0.709(2) 0.1167(8) 0.106(3) Uani 1 1 d . . . . .
H14A H 0.726111 0.885099 0.126677 0.127 Uiso 1 1 calc R U . . .
H14B H 0.709930 0.676187 0.042785 0.127 Uiso 1 1 calc R U . . .
C15 C 0.8290(8) 0.603(3) 0.1748(8) 0.133(5) Uani 1 1 d . . . . .
H15A H 0.883581 0.667190 0.147863 0.200 Uiso 1 1 calc R U . . .
H15B H 0.826058 0.427961 0.167169 0.200 Uiso 1 1 calc R U . . .
H15C H 0.845104 0.644402 0.247332 0.200 Uiso 1 1 calc R U . . .
C16 C 0.7860(6) 0.5091(15) 0.4880(6) 0.0683(19) Uani 1 1 d . . . . .
C17 C 0.8531(6) 0.7039(16) 0.4905(6) 0.077(2) Uani 1 1 d . . . . .
H17 H 0.833892 0.825659 0.439899 0.093 Uiso 1 1 calc R U . . .
C18 C 0.9497(7) 0.7173(18) 0.5692(7) 0.086(3) Uani 1 1 d . . . . .
H18 H 0.996179 0.847333 0.571330 0.104 Uiso 1 1 calc R U . . .
C19 C 0.9764(7) 0.5365(19) 0.6440(7) 0.087(3) Uani 1 1 d . . . . .
H19 H 1.040545 0.546684 0.697442 0.105 Uiso 1 1 calc R U . . .
C20 C 0.9089(6) 0.3407(18) 0.6407(6) 0.081(2) Uani 1 1 d . . . . .
H20 H 0.927992 0.217830 0.690816 0.097 Uiso 1 1 calc R U . . .
C21 C 0.8125(6) 0.3285(17) 0.5619(6) 0.075(2) Uani 1 1 d . . . . .
H21 H 0.766034 0.198224 0.559364 0.090 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 C9 1.371(10) . ?
O1 C3 1.201(9) . ?
O2 C4 1.213(9) . ?
O3 C13 1.210(9) . ?
O4 C13 1.331(10) . ?
O4 C14 1.463(10) . ?
N1 C3 1.374(10) . ?
N1 C4 1.399(10) . ?
N1 C16 1.442(9) . ?
C1 C4 1.503(10) . ?
C1 C5 1.530(9) . ?
C1 C2 1.546(12) . ?
C2 C3 1.509(10) . ?
C2 C12 1.521(9) . ?
C5 C6 1.508(10) . ?
C6 C11 1.361(11) . ?
C6 C7 1.375(12) . ?
C7 C8 1.390(12) . ?
C8 C9 1.351(13) . ?
C9 C10 1.336(13) . ?
C10 C11 1.392(11) . ?
C12 C13 1.501(12) . ?
C14 C15 1.474(13) . ?
C16 C21 1.368(11) . ?
C16 C17 1.374(11) . ?
C17 C18 1.389(11) . ?
C18 C19 1.377(12) . ?
C19 C20 1.379(12) . ?
C20 C21 1.386(10) . ?

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
C13 O4 C14 117.8(7) . . ?
C3 N1 C4 112.3(6) . . ?
C3 N1 C16 125.5(6) . . ?
C4 N1 C16 122.2(6) . . ?
C4 C1 C5 111.0(6) . . ?
C4 C1 C2 103.3(6) . . ?
C5 C1 C2 116.0(7) . . ?
C3 C2 C12 113.6(6) . . ?
C3 C2 C1 104.8(7) . . ?
C12 C2 C1 117.5(7) . . ?
O1 C3 N1 124.7(7) . . ?
O1 C3 C2 127.0(7) . . ?
N1 C3 C2 108.3(7) . . ?
O2 C4 N1 124.3(7) . . ?
O2 C4 C1 126.4(7) . . ?
N1 C4 C1 109.3(7) . . ?
C6 C5 C1 114.0(6) . . ?
C11 C6 C7 117.9(8) . . ?
C11 C6 C5 121.3(8) . . ?
C7 C6 C5 120.8(7) . . ?
C6 C7 C8 122.2(9) . . ?
C9 C8 C7 116.8(9) . . ?
C10 C9 C8 123.5(9) . . ?
C10 C9 F1 117.1(10) . . ?
C8 C9 F1 119.5(10) . . ?
C9 C10 C11 118.8(9) . . ?
C6 C11 C10 120.8(9) . . ?
C13 C12 C2 115.8(7) . . ?
O3 C13 O4 123.7(9) . . ?
O3 C13 C12 124.0(9) . . ?
O4 C13 C12 112.3(7) . . ?
O4 C14 C15 108.9(8) . . ?
C21 C16 C17 121.2(7) . . ?
C21 C16 N1 118.9(7) . . ?
C17 C16 N1 119.9(7) . . ?
C16 C17 C18 119.4(8) . . ?
C19 C18 C17 119.5(9) . . ?
C18 C19 C20 120.8(8) . . ?
C19 C20 C21 119.4(8) . . ?
C16 C21 C20 119.7(8) . . ?

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
C4 C1 C2 C3 -13.4(8) . . . . ?
C5 C1 C2 C3 -135.1(6) . . . . ?
C4 C1 C2 C12 -140.6(7) . . . . ?
C5 C1 C2 C12 97.7(8) . . . . ?
C4 N1 C3 O1 172.1(7) . . . . ?
C16 N1 C3 O1 -6.9(12) . . . . ?
C4 N1 C3 C2 -7.9(8) . . . . ?
C16 N1 C3 C2 173.1(7) . . . . ?
C12 C2 C3 O1 -37.1(12) . . . . ?
C1 C2 C3 O1 -166.7(8) . . . . ?
C12 C2 C3 N1 142.9(7) . . . . ?
C1 C2 C3 N1 13.4(8) . . . . ?
C3 N1 C4 O2 179.0(8) . . . . ?
C16 N1 C4 O2 -1.9(12) . . . . ?
C3 N1 C4 C1 -1.2(8) . . . . ?
C16 N1 C4 C1 177.8(7) . . . . ?
C5 C1 C4 O2 -45.9(12) . . . . ?
C2 C1 C4 O2 -170.9(8) . . . . ?
C5 C1 C4 N1 134.4(7) . . . . ?
C2 C1 C4 N1 9.4(8) . . . . ?
C4 C1 C5 C6 -178.9(8) . . . . ?
C2 C1 C5 C6 -61.4(10) . . . . ?
C1 C5 C6 C11 -64.1(11) . . . . ?
C1 C5 C6 C7 115.0(9) . . . . ?
C11 C6 C7 C8 0.0(13) . . . . ?
C5 C6 C7 C8 -179.1(8) . . . . ?
C6 C7 C8 C9 0.4(14) . . . . ?
C7 C8 C9 C10 -1.6(15) . . . . ?
C7 C8 C9 F1 180.0(8) . . . . ?
C8 C9 C10 C11 2.1(15) . . . . ?
F1 C9 C10 C11 -179.4(9) . . . . ?
C7 C6 C11 C10 0.5(13) . . . . ?
C5 C6 C11 C10 179.7(8) . . . . ?
C9 C10 C11 C6 -1.5(14) . . . . ?
C3 C2 C12 C13 -46.3(10) . . . . ?
C1 C2 C12 C13 76.5(9) . . . . ?
C14 O4 C13 O3 -6.0(12) . . . . ?
C14 O4 C13 C12 174.1(7) . . . . ?
C2 C12 C13 O3 158.2(9) . . . . ?
C2 C12 C13 O4 -21.9(10) . . . . ?
C13 O4 C14 C15 -95.2(10) . . . . ?
C3 N1 C16 C21 -65.1(10) . . . . ?
C4 N1 C16 C21 116.0(8) . . . . ?
C3 N1 C16 C17 116.0(8) . . . . ?
C4 N1 C16 C17 -62.9(9) . . . . ?
C21 C16 C17 C18 0.3(12) . . . . ?
N1 C16 C17 C18 179.1(7) . . . . ?
C16 C17 C18 C19 -0.6(12) . . . . ?
C17 C18 C19 C20 1.1(13) . . . . ?
C18 C19 C20 C21 -1.1(13) . . . . ?
C17 C16 C21 C20 -0.3(12) . . . . ?
N1 C16 C21 C20 -179.2(7) . . . . ?
C19 C20 C21 C16 0.7(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O4 0.98 2.51 3.003(9) 110.7 . yes
C17 H17 O1 0.93 2.64 3.520(10) 158.7 1_565 yes

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.050

