# 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. 
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data_tp_tps_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2388928'
loop_
_audit_author_name
_audit_author_address
'TRIPTI PAUL'
;INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI
India
;
_audit_update_record             
;
2024-10-05 deposited with the CCDC.	2025-05-21 downloaded from the CCDC.
;
_audit_creation_date             2024-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 F O3 P S'
_chemical_formula_sum            'C17 H14 F O3 P S'
_chemical_formula_weight         348.31
_chemical_absolute_configuration unk
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   7.7392(9)
_cell_length_b                   13.4287(15)
_cell_length_c                   15.1509(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1574.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1110 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.9070.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            39511
_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         26.365
_diffrn_reflns_theta_min         2.026
_diffrn_ambient_temperature      301.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_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           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3032
_reflns_number_total             3220
_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.
;
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.47(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.073
_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)+(0.0328P)²+0.5946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0790
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.53(10)
 0.47(10)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S1 S 0.66687(10) 0.76780(5) 0.48998(5) 0.0484(2) Uani 1 1 d . . . . .
P1 P 0.45212(8) 0.43716(5) 0.49734(5) 0.03753(17) Uani 1 1 d . . . . .
F1 F 0.4684(3) 0.58072(13) 0.75337(12) 0.0625(5) Uani 1 1 d . . . . .
O1 O 0.5144(3) 0.50857(14) 0.57564(12) 0.0452(5) Uani 1 1 d . . . . .
O2 O 0.4953(3) 0.33495(13) 0.52035(14) 0.0510(5) Uani 1 1 d . . . . .
O3 O 0.2555(2) 0.45942(15) 0.48665(15) 0.0516(5) Uani 1 1 d . . . . .
C1 C 0.5694(4) 0.6762(2) 0.63324(18) 0.0388(6) Uani 1 1 d . . . . .
C2 C 0.5309(4) 0.6687(2) 0.72290(18) 0.0453(7) Uani 1 1 d . . . . .
C3 C 0.5510(4) 0.7462(2) 0.7795(2) 0.0521(7) Uani 1 1 d . . . . .
H3 H 0.523815 0.738964 0.838919 0.062 Uiso 1 1 calc R U . . .
C4 C 0.6127(5) 0.8366(2) 0.7474(2) 0.0541(8) Uani 1 1 d . . . . .
H4 H 0.628638 0.889306 0.786371 0.065 Uiso 1 1 calc R U . . .
C5 C 0.6507(4) 0.8499(2) 0.6596(2) 0.0517(7) Uani 1 1 d . . . . .
H5 H 0.690042 0.910910 0.638528 0.062 Uiso 1 1 calc R U . . .
C6 C 0.6285(4) 0.7691(2) 0.60307(18) 0.0418(6) Uani 1 1 d . . . . .
C7 C 0.6085(3) 0.64263(18) 0.48290(18) 0.0379(6) Uani 1 1 d . . . . .
C8 C 0.5608(4) 0.60674(19) 0.56219(17) 0.0372(6) Uani 1 1 d . . . . .
C9 C 0.6117(4) 0.5865(2) 0.40088(18) 0.0381(6) Uani 1 1 d . . . . .
C10 C 0.5414(4) 0.4893(2) 0.39909(17) 0.0379(6) Uani 1 1 d . . . . .
C11 C 0.6814(4) 0.6266(2) 0.32410(19) 0.0477(7) Uani 1 1 d . . . . .
H11 H 0.729822 0.689972 0.325015 0.057 Uiso 1 1 calc R U . . .
C12 C 0.6791(5) 0.5729(3) 0.2468(2) 0.0559(8) Uani 1 1 d . . . . .
H12 H 0.725299 0.600336 0.195637 0.067 Uiso 1 1 calc R U . . .
C13 C 0.6089(5) 0.4789(3) 0.2448(2) 0.0559(8) Uani 1 1 d . . . . .
H13 H 0.608014 0.443713 0.191929 0.067 Uiso 1 1 calc R U . . .
C14 C 0.5391(4) 0.4352(2) 0.32027(19) 0.0462(6) Uani 1 1 d . . . . .
C15 C 0.1227(5) 0.4008(3) 0.5295(3) 0.0715(11) Uani 1 1 d . . . . .
H15A H 0.129657 0.409508 0.592938 0.086 Uiso 1 1 calc R U . . .
H15B H 0.139556 0.330780 0.516298 0.086 Uiso 1 1 calc R U . . .
C16 C -0.0474(4) 0.4331(3) 0.4976(3) 0.0721(10) Uani 1 1 d . . . . .
H16A H -0.068984 0.500102 0.516902 0.108 Uiso 1 1 calc R U . . .
H16B H -0.134962 0.389819 0.520894 0.108 Uiso 1 1 calc R U . . .
H16C H -0.049531 0.430643 0.434335 0.108 Uiso 1 1 calc R U . . .
C17 C 0.4640(6) 0.3317(3) 0.3133(2) 0.0682(10) Uani 1 1 d . . . . .
H17A H 0.532024 0.286375 0.347830 0.102 Uiso 1 1 calc R U . . .
H17B H 0.464745 0.310793 0.252663 0.102 Uiso 1 1 calc R U . . .
H17C H 0.347332 0.332028 0.334850 0.102 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
S1 C6 1.739(3) . ?
S1 C7 1.744(3) . ?
P1 O1 1.600(2) . ?
P1 O2 1.4550(19) . ?
P1 O3 1.559(2) . ?
P1 C10 1.784(3) . ?
F1 C2 1.357(3) . ?
O1 C8 1.381(3) . ?
O3 C15 1.448(4) . ?
C1 C2 1.394(4) . ?
C1 C6 1.406(4) . ?
C1 C8 1.426(4) . ?
C2 C3 1.357(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(4) . ?
C7 C8 1.346(4) . ?
C7 C9 1.453(4) . ?
C9 C10 1.415(4) . ?
C9 C11 1.390(4) . ?
C10 C14 1.398(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.395(4) . ?
C14 C17 1.511(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.468(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C6 S1 C7 91.51(13) . . ?
O1 P1 C10 105.46(11) . . ?
O2 P1 O1 108.57(12) . . ?
O2 P1 O3 115.46(12) . . ?
O2 P1 C10 118.77(13) . . ?
O3 P1 O1 104.84(13) . . ?
O3 P1 C10 102.48(12) . . ?
C8 O1 P1 122.74(16) . . ?
C15 O3 P1 122.8(2) . . ?
C2 C1 C6 116.8(2) . . ?
C2 C1 C8 132.7(3) . . ?
C6 C1 C8 110.5(2) . . ?
F1 C2 C1 118.1(2) . . ?
C3 C2 F1 119.6(3) . . ?
C3 C2 C1 122.4(3) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.6(3) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.9(3) . . ?
C6 C5 H5 121.1 . . ?
C1 C6 S1 111.5(2) . . ?
C5 C6 S1 126.3(2) . . ?
C5 C6 C1 122.2(3) . . ?
C8 C7 S1 111.2(2) . . ?
C8 C7 C9 125.6(2) . . ?
C9 C7 S1 123.2(2) . . ?
O1 C8 C1 121.7(2) . . ?
C7 C8 O1 123.0(2) . . ?
C7 C8 C1 115.3(2) . . ?
C10 C9 C7 119.2(2) . . ?
C11 C9 C7 121.4(3) . . ?
C11 C9 C10 119.3(3) . . ?
C9 C10 P1 119.7(2) . . ?
C14 C10 P1 120.2(2) . . ?
C14 C10 C9 120.1(3) . . ?
C9 C11 H11 119.9 . . ?
C12 C11 C9 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C10 C14 C17 122.9(3) . . ?
C13 C14 C10 118.5(3) . . ?
C13 C14 C17 118.6(3) . . ?
O3 C15 H15A 109.8 . . ?
O3 C15 H15B 109.8 . . ?
O3 C15 C16 109.2(3) . . ?
H15A C15 H15B 108.3 . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
S1 C7 C8 O1 -177.6(2) . . . . ?
S1 C7 C8 C1 -0.6(3) . . . . ?
S1 C7 C9 C10 -172.0(2) . . . . ?
S1 C7 C9 C11 7.7(4) . . . . ?
P1 O1 C8 C1 162.3(2) . . . . ?
P1 O1 C8 C7 -20.8(4) . . . . ?
P1 O3 C15 C16 -173.2(3) . . . . ?
P1 C10 C14 C13 179.5(2) . . . . ?
P1 C10 C14 C17 -0.3(4) . . . . ?
F1 C2 C3 C4 -179.0(3) . . . . ?
O1 P1 O3 C15 -94.8(3) . . . . ?
O1 P1 C10 C9 -13.2(3) . . . . ?
O1 P1 C10 C14 168.0(2) . . . . ?
O2 P1 O1 C8 151.9(2) . . . . ?
O2 P1 O3 C15 24.6(3) . . . . ?
O2 P1 C10 C9 -135.1(2) . . . . ?
O2 P1 C10 C14 46.1(3) . . . . ?
O3 P1 O1 C8 -84.1(2) . . . . ?
O3 P1 C10 C9 96.3(2) . . . . ?
O3 P1 C10 C14 -82.5(3) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C1 C6 S1 -178.8(2) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
C2 C1 C8 O1 -3.5(5) . . . . ?
C2 C1 C8 C7 179.5(3) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 S1 179.7(3) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C6 S1 C7 C8 1.0(2) . . . . ?
C6 S1 C7 C9 -179.2(2) . . . . ?
C6 C1 C2 F1 177.9(3) . . . . ?
C6 C1 C2 C3 -0.9(5) . . . . ?
C6 C1 C8 O1 176.8(3) . . . . ?
C6 C1 C8 C7 -0.3(4) . . . . ?
C7 S1 C6 C1 -1.1(2) . . . . ?
C7 S1 C6 C5 179.1(3) . . . . ?
C7 C9 C10 P1 -0.5(4) . . . . ?
C7 C9 C10 C14 178.3(3) . . . . ?
C7 C9 C11 C12 -178.4(3) . . . . ?
C8 C1 C2 F1 -1.7(5) . . . . ?
C8 C1 C2 C3 179.4(3) . . . . ?
C8 C1 C6 S1 1.0(3) . . . . ?
C8 C1 C6 C5 -179.2(3) . . . . ?
C8 C7 C9 C10 7.8(4) . . . . ?
C8 C7 C9 C11 -172.6(3) . . . . ?
C9 C7 C8 O1 2.6(4) . . . . ?
C9 C7 C8 C1 179.6(2) . . . . ?
C9 C10 C14 C13 0.7(4) . . . . ?
C9 C10 C14 C17 -179.1(3) . . . . ?
C9 C11 C12 C13 -0.4(5) . . . . ?
C10 P1 O1 C8 23.6(3) . . . . ?
C10 P1 O3 C15 155.2(3) . . . . ?
C10 C9 C11 C12 1.2(4) . . . . ?
C11 C9 C10 P1 179.9(2) . . . . ?
C11 C9 C10 C14 -1.3(4) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 C10 0.1(5) . . . . ?
C12 C13 C14 C17 179.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.53(10)
2 0.47(10)

