# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_4-Fspart
_database_code_depnum_ccdc_archive 'CCDC 2201897'
loop_
_audit_author_name
_audit_author_address
'ASHISH KUMAR SAHOO'
;IIT GUWAHATI
India
;
_audit_update_record             
;
2022-08-17 deposited with the CCDC.	2023-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H15 F N2 S'
_chemical_formula_weight         382.44

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'
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'
S S 0.1246 0.1234 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.2258(5)
_cell_length_b                   8.0745(3)
_cell_length_c                   19.2139(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.3170(10)
_cell_angle_gamma                90
_cell_volume                     1936.37(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.72

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   none
_diffrn_ambient_temperature      297(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            32809
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3414
_reflns_number_gt                2595
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 (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)+(0.0486P)²+0.6826P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3414
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_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
S1 S 0.52791(5) 0.66236(8) 0.72338(3) 0.0737(2) Uani 1 1 d . . . . .
N1 N 0.54836(13) 0.4446(2) 0.62391(9) 0.0573(4) Uani 1 1 d . . . . .
F2 F 0.98688(13) 0.6988(3) 0.76960(9) 0.1364(8) Uani 1 1 d . . . . .
C2 C 0.36781(15) 0.4967(2) 0.61979(10) 0.0520(5) Uani 1 1 d . . . . .
C3 C 0.32761(15) 0.3921(2) 0.55873(10) 0.0507(4) Uani 1 1 d . . . . .
N2 N 0.24640(16) 0.6563(2) 0.67708(12) 0.0794(6) Uani 1 1 d . . . . .
C18 C 0.21163(15) 0.3569(2) 0.52500(10) 0.0518(5) Uani 1 1 d . . . . .
C5 C 0.51029(15) 0.3409(2) 0.56579(10) 0.0517(5) Uani 1 1 d . . . . .
C1 C 0.47904(16) 0.5204(2) 0.64919(11) 0.0553(5) Uani 1 1 d . . . . .
C4 C 0.40146(15) 0.3173(2) 0.53177(10) 0.0536(5) Uani 1 1 d . . . . .
H4 H 0.377464 0.250148 0.490196 0.064 Uiso 1 1 calc R U . . .
C6 C 0.59217(15) 0.2530(2) 0.54293(11) 0.0553(5) Uani 1 1 d . . . . .
C19 C 0.15236(16) 0.3056(3) 0.56804(12) 0.0627(5) Uani 1 1 d . . . . .
H19 H 0.184456 0.299400 0.618952 0.075 Uiso 1 1 calc R U . . .
C12 C 0.66564(17) 0.6701(3) 0.73378(11) 0.0615(5) Uani 1 1 d . . . . .
C24 C 0.29861(17) 0.5852(3) 0.65073(11) 0.0595(5) Uani 1 1 d . . . . .
C11 C 0.56723(19) 0.1767(3) 0.47456(12) 0.0645(6) Uani 1 1 d . . . . .
H11 H 0.497326 0.180587 0.441959 0.077 Uiso 1 1 calc R U . . .
C10 C 0.6454(2) 0.0948(3) 0.45435(14) 0.0753(7) Uani 1 1 d . . . . .
H10 H 0.627812 0.044887 0.408255 0.090 Uiso 1 1 calc R U . . .
C23 C 0.16209(18) 0.3669(3) 0.44953(12) 0.0703(6) Uani 1 1 d . . . . .
H23 H 0.200937 0.400455 0.419549 0.084 Uiso 1 1 calc R U . . .
C13 C 0.7087(2) 0.8113(3) 0.71470(12) 0.0713(6) Uani 1 1 d . . . . .
H13 H 0.664673 0.900444 0.693704 0.086 Uiso 1 1 calc R U . . .
C17 C 0.7319(2) 0.5387(3) 0.76429(13) 0.0757(6) Uani 1 1 d . . . . .
H17 H 0.702922 0.443550 0.777458 0.091 Uiso 1 1 calc R U . . .
C21 C -0.00248(19) 0.2749(3) 0.46200(14) 0.0812(7) Uani 1 1 d . . . . .
H21 H -0.074446 0.247261 0.440891 0.097 Uiso 1 1 calc R U . . .
C9 C 0.7484(2) 0.0873(3) 0.50210(18) 0.0840(8) Uani 1 1 d . . . . .
H9 H 0.800940 0.033153 0.488332 0.101 Uiso 1 1 calc R U . . .
C20 C 0.04607(18) 0.2635(3) 0.53639(14) 0.0758(7) Uani 1 1 d . . . . .
H20 H 0.007247 0.227129 0.565927 0.091 Uiso 1 1 calc R U . . .
C7 C 0.69703(17) 0.2433(3) 0.59051(14) 0.0747(6) Uani 1 1 d . . . . .
H7 H 0.715597 0.293589 0.636581 0.090 Uiso 1 1 calc R U . . .
C16 C 0.8393(2) 0.5457(4) 0.77555(14) 0.0882(8) Uani 1 1 d . . . . .
H16 H 0.883603 0.456049 0.795444 0.106 Uiso 1 1 calc R U . . .
C22 C 0.0546(2) 0.3270(3) 0.41850(13) 0.0837(7) Uani 1 1 d . . . . .
H22 H 0.021183 0.335755 0.367789 0.100 Uiso 1 1 calc R U . . .
C15 C 0.8796(2) 0.6866(5) 0.75697(13) 0.0891(8) Uani 1 1 d . . . . .
C8 C 0.7740(2) 0.1599(3) 0.57029(17) 0.0895(8) Uani 1 1 d . . . . .
H8 H 0.843686 0.152936 0.603076 0.107 Uiso 1 1 calc R U . . .
C14 C 0.8180(2) 0.8203(4) 0.72683(13) 0.0877(8) Uani 1 1 d . . . . .
H14 H 0.848302 0.915280 0.714696 0.105 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 C12 1.767(2) . ?
S1 C1 1.776(2) . ?
N1 C1 1.321(2) . ?
N1 C5 1.352(2) . ?
F2 C15 1.361(3) . ?
C2 C3 1.400(3) . ?
C2 C1 1.404(3) . ?
C2 C24 1.436(3) . ?
C3 C4 1.386(3) . ?
C3 C18 1.482(3) . ?
N2 C24 1.138(3) . ?
C18 C19 1.378(3) . ?
C18 C23 1.382(3) . ?
C5 C4 1.383(3) . ?
C5 C6 1.478(3) . ?
C4 H4 0.9300 . ?
C6 C7 1.388(3) . ?
C6 C11 1.388(3) . ?
C19 C20 1.377(3) . ?
C19 H19 0.9300 . ?
C12 C13 1.377(3) . ?
C12 C17 1.377(3) . ?
C11 C10 1.387(3) . ?
C11 H11 0.9300 . ?
C10 C9 1.370(4) . ?
C10 H10 0.9300 . ?
C23 C22 1.385(3) . ?
C23 H23 0.9300 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C17 C16 1.366(3) . ?
C17 H17 0.9300 . ?
C21 C20 1.363(3) . ?
C21 C22 1.365(3) . ?
C21 H21 0.9300 . ?
C9 C8 1.372(4) . ?
C9 H9 0.9300 . ?
C20 H20 0.9300 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9300 . ?
C16 C15 1.353(4) . ?
C16 H16 0.9300 . ?
C22 H22 0.9300 . ?
C15 C14 1.362(4) . ?
C8 H8 0.9300 . ?
C14 H14 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
C12 S1 C1 101.63(9) . . ?
C1 N1 C5 118.43(17) . . ?
C3 C2 C1 118.46(17) . . ?
C3 C2 C24 122.00(17) . . ?
C1 C2 C24 119.48(17) . . ?
C4 C3 C2 117.18(17) . . ?
C4 C3 C18 120.56(17) . . ?
C2 C3 C18 122.24(17) . . ?
C19 C18 C23 118.75(18) . . ?
C19 C18 C3 120.48(17) . . ?
C23 C18 C3 120.69(18) . . ?
N1 C5 C4 121.38(17) . . ?
N1 C5 C6 115.69(17) . . ?
C4 C5 C6 122.91(17) . . ?
N1 C1 C2 123.45(18) . . ?
N1 C1 S1 118.78(15) . . ?
C2 C1 S1 117.76(15) . . ?
C5 C4 C3 120.99(18) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C7 C6 C11 118.1(2) . . ?
C7 C6 C5 120.13(19) . . ?
C11 C6 C5 121.75(19) . . ?
C20 C19 C18 120.6(2) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C13 C12 C17 119.3(2) . . ?
C13 C12 S1 120.09(18) . . ?
C17 C12 S1 120.49(18) . . ?
N2 C24 C2 177.9(2) . . ?
C10 C11 C6 120.7(2) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C18 C23 C22 120.0(2) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C12 C13 C14 119.9(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C16 C17 C12 121.1(2) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C20 C21 C22 119.9(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C21 C20 C19 120.3(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C15 C16 C17 118.2(3) . . ?
C15 C16 H16 120.9 . . ?
C17 C16 H16 120.9 . . ?
C21 C22 C23 120.3(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C16 C15 F2 119.5(3) . . ?
C16 C15 C14 123.1(3) . . ?
F2 C15 C14 117.4(3) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C15 C14 C13 118.3(3) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?

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
C1 C2 C3 C4 0.6(3) . . . . ?
C24 C2 C3 C4 177.77(17) . . . . ?
C1 C2 C3 C18 178.67(17) . . . . ?
C24 C2 C3 C18 -4.1(3) . . . . ?
C4 C3 C18 C19 127.0(2) . . . . ?
C2 C3 C18 C19 -51.0(3) . . . . ?
C4 C3 C18 C23 -49.8(3) . . . . ?
C2 C3 C18 C23 132.2(2) . . . . ?
C1 N1 C5 C4 1.8(3) . . . . ?
C1 N1 C5 C6 -176.68(17) . . . . ?
C5 N1 C1 C2 1.3(3) . . . . ?
C5 N1 C1 S1 -177.76(14) . . . . ?
C3 C2 C1 N1 -2.5(3) . . . . ?
C24 C2 C1 N1 -179.72(18) . . . . ?
C3 C2 C1 S1 176.58(14) . . . . ?
C24 C2 C1 S1 -0.7(2) . . . . ?
C12 S1 C1 N1 5.89(18) . . . . ?
C12 S1 C1 C2 -173.20(16) . . . . ?
N1 C5 C4 C3 -3.6(3) . . . . ?
C6 C5 C4 C3 174.72(17) . . . . ?
C2 C3 C4 C5 2.3(3) . . . . ?
C18 C3 C4 C5 -175.82(17) . . . . ?
N1 C5 C6 C7 17.2(3) . . . . ?
C4 C5 C6 C7 -161.2(2) . . . . ?
N1 C5 C6 C11 -163.54(18) . . . . ?
C4 C5 C6 C11 18.0(3) . . . . ?
C23 C18 C19 C20 0.7(3) . . . . ?
C3 C18 C19 C20 -176.2(2) . . . . ?
C1 S1 C12 C13 110.18(18) . . . . ?
C1 S1 C12 C17 -73.00(19) . . . . ?
C7 C6 C11 C10 -0.7(3) . . . . ?
C5 C6 C11 C10 -179.96(18) . . . . ?
C6 C11 C10 C9 0.5(3) . . . . ?
C19 C18 C23 C22 0.5(3) . . . . ?
C3 C18 C23 C22 177.3(2) . . . . ?
C17 C12 C13 C14 -0.5(3) . . . . ?
S1 C12 C13 C14 176.36(17) . . . . ?
C13 C12 C17 C16 -0.4(3) . . . . ?
S1 C12 C17 C16 -177.21(18) . . . . ?
C11 C10 C9 C8 0.5(4) . . . . ?
C22 C21 C20 C19 0.5(4) . . . . ?
C18 C19 C20 C21 -1.2(4) . . . . ?
C11 C6 C7 C8 -0.1(3) . . . . ?
C5 C6 C7 C8 179.2(2) . . . . ?
C12 C17 C16 C15 1.0(4) . . . . ?
C20 C21 C22 C23 0.6(4) . . . . ?
C18 C23 C22 C21 -1.1(4) . . . . ?
C17 C16 C15 F2 178.1(2) . . . . ?
C17 C16 C15 C14 -0.9(4) . . . . ?
C10 C9 C8 C7 -1.3(4) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C16 C15 C14 C13 0.0(4) . . . . ?
F2 C15 C14 C13 -178.9(2) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.030

