# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc2fr4kx
_database_code_depnum_ccdc_archive 'CCDC 2256569'
loop_
_audit_author_name
_audit_author_address
'Ishu '
;Banaras Hindu University
India
;
_audit_update_record             
;
2023-04-15 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H20 F2 O3 S'
_chemical_formula_weight         366.41

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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   21.1418(11)
_cell_length_b                   6.3999(3)
_cell_length_c                   27.7760(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.557(4)
_cell_angle_gamma                90
_cell_volume                     3733.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    285(2)
_cell_measurement_reflns_used    4856
_cell_measurement_theta_min      3.1370
_cell_measurement_theta_max      71.8380

_exptl_crystal_description       Needle-shaped
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             1536.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.843
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      285(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12893
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.203
_diffrn_reflns_theta_max         71.850
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3655
_reflns_number_gt                2004
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1921P)²] 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         3594
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1546
_refine_ls_R_factor_gt           0.1060
_refine_ls_wR_factor_ref         0.3195
_refine_ls_wR_factor_gt          0.2711
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
S1 S 0.21853(6) 0.5669(2) 0.30518(4) 0.0666(5) Uani 1 1 d . . . . .
O3 O 0.34328(17) 0.7104(5) 0.36021(11) 0.0710(10) Uani 1 1 d . . . . .
O2 O 0.18002(17) 0.4664(6) 0.26635(12) 0.0786(11) Uani 1 1 d . . . . .
O1 O 0.21716(18) 0.7909(5) 0.30771(13) 0.0780(11) Uani 1 1 d . . . . .
C13 C 0.4130(2) 0.4784(8) 0.3212(2) 0.0692(13) Uani 1 1 d . . . . .
C11 C 0.2958(2) 0.4791(8) 0.30225(18) 0.0658(12) Uani 1 1 d . . . . .
H11 H 0.300368 0.366642 0.281739 0.079 Uiso 1 1 calc R U . . .
C12 C 0.3487(3) 0.5541(7) 0.32585(18) 0.0657(12) Uani 1 1 d . . . . .
C8 C 0.1958(2) 0.4682(7) 0.35986(17) 0.0613(12) Uani 1 1 d . . . . .
F2 F 0.4174(3) 0.9492(7) 0.3701(3) 0.165(2) Uani 1 1 d . . . . .
F1 F 0.3245(3) 1.0396(7) 0.3680(2) 0.155(2) Uani 1 1 d . . . . .
C9 C 0.1993(3) 0.5897(8) 0.4002(2) 0.0730(14) Uani 1 1 d . . . . .
H9 H 0.216389 0.723343 0.399524 0.088 Uiso 1 1 calc R U . . .
C5 C 0.1516(3) 0.3183(8) 0.44449(19) 0.0719(13) Uani 1 1 d . . . . .
C18 C 0.4609(3) 0.4867(10) 0.3581(2) 0.0876(17) Uani 1 1 d . . . . .
H18 H 0.453758 0.550669 0.387103 0.105 Uiso 1 1 calc R U . . .
C10 C 0.1774(3) 0.5158(9) 0.4426(2) 0.0798(15) Uani 1 1 d . . . . .
H10 H 0.180161 0.600891 0.469863 0.096 Uiso 1 1 calc R U . . .
C7 C 0.1719(3) 0.2669(9) 0.3610(2) 0.0846(17) Uani 1 1 d . . . . .
H7 H 0.170763 0.180395 0.333977 0.102 Uiso 1 1 calc R U . . .
C14 C 0.4246(3) 0.3826(10) 0.2781(2) 0.0877(17) Uani 1 1 d . . . . .
H14 H 0.392483 0.375138 0.252311 0.105 Uiso 1 1 calc R U . . .
C6 C 0.1502(3) 0.1984(9) 0.4026(2) 0.0922(19) Uani 1 1 d . . . . .
H6 H 0.133447 0.064036 0.403048 0.111 Uiso 1 1 calc R U . . .
C19 C 0.3626(4) 0.9082(10) 0.3483(2) 0.100(2) Uani 1 1 d . . . . .
H19 H 0.360898 0.927570 0.313206 0.120 Uiso 1 1 calc R U . . .
C16 C 0.5306(4) 0.3075(12) 0.3111(4) 0.118(3) Uani 1 1 d . . . . .
H16 H 0.570157 0.249060 0.307940 0.142 Uiso 1 1 calc R U . . .
C15 C 0.4838(3) 0.2987(11) 0.2735(3) 0.109(2) Uani 1 1 d . . . . .
H15 H 0.491597 0.235992 0.244581 0.130 Uiso 1 1 calc R U . . .
C1 C 0.1238(4) 0.2418(11) 0.4894(2) 0.099(2) Uani 1 1 d . . . . .
C17 C 0.5199(3) 0.4019(13) 0.3535(3) 0.110(2) Uani 1 1 d . . . . .
H17 H 0.552177 0.408884 0.379156 0.132 Uiso 1 1 calc R U . . .
C3 C 0.1390(5) 0.3735(14) 0.5329(3) 0.137(3) Uani 1 1 d . . . . .
H3A H 0.112466 0.333867 0.557216 0.206 Uiso 1 1 calc R U . . .
H3B H 0.131620 0.517540 0.524462 0.206 Uiso 1 1 calc R U . . .
H3C H 0.182926 0.354531 0.545340 0.206 Uiso 1 1 calc R U . . .
C2 C 0.1441(13) 0.0278(18) 0.5014(5) 0.337(15) Uani 1 1 d . . . . .
H2A H 0.134476 -0.059851 0.473520 0.506 Uiso 1 1 calc R U . . .
H2B H 0.189097 0.025747 0.511291 0.506 Uiso 1 1 calc R U . . .
H2C H 0.121967 -0.022991 0.527423 0.506 Uiso 1 1 calc R U . . .
C4 C 0.0527(6) 0.252(4) 0.4793(4) 0.284(12) Uani 1 1 d . . . . .
H4A H 0.039995 0.393410 0.471420 0.425 Uiso 1 1 calc R U . . .
H4B H 0.038676 0.162591 0.452437 0.425 Uiso 1 1 calc R U . . .
H4C H 0.033848 0.207627 0.507374 0.425 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 O2 1.428(4) . ?
S1 O1 1.436(4) . ?
S1 C11 1.738(5) . ?
S1 C8 1.762(5) . ?
O3 C19 1.381(7) . ?
O3 C12 1.397(6) . ?
C13 C18 1.358(8) . ?
C13 C14 1.392(8) . ?
C13 C12 1.462(7) . ?
C11 C12 1.321(7) . ?
C8 C9 1.358(7) . ?
C8 C7 1.385(7) . ?
F2 C19 1.272(8) . ?
F1 C19 1.324(8) . ?
C9 C10 1.396(8) . ?
C5 C10 1.380(7) . ?
C5 C6 1.391(8) . ?
C5 C1 1.521(8) . ?
C18 C17 1.380(9) . ?
C7 C6 1.366(8) . ?
C14 C15 1.381(9) . ?
C16 C15 1.353(11) . ?
C16 C17 1.367(11) . ?
C1 C2 1.462(12) . ?
C1 C3 1.478(10) . ?
C1 C4 1.499(14) . ?

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
O2 S1 O1 118.3(2) . . ?
O2 S1 C11 106.1(2) . . ?
O1 S1 C11 110.4(2) . . ?
O2 S1 C8 107.5(2) . . ?
O1 S1 C8 107.9(2) . . ?
C11 S1 C8 106.0(2) . . ?
C19 O3 C12 116.3(4) . . ?
C18 C13 C14 118.5(6) . . ?
C18 C13 C12 122.7(5) . . ?
C14 C13 C12 118.7(5) . . ?
C12 C11 S1 127.4(4) . . ?
C11 C12 O3 117.9(5) . . ?
C11 C12 C13 125.4(5) . . ?
O3 C12 C13 116.6(4) . . ?
C9 C8 C7 120.0(5) . . ?
C9 C8 S1 120.7(4) . . ?
C7 C8 S1 119.2(4) . . ?
C8 C9 C10 120.6(5) . . ?
C10 C5 C6 116.4(5) . . ?
C10 C5 C1 121.2(5) . . ?
C6 C5 C1 122.3(5) . . ?
C13 C18 C17 121.2(7) . . ?
C5 C10 C9 120.9(5) . . ?
C6 C7 C8 118.4(5) . . ?
C15 C14 C13 120.1(7) . . ?
C7 C6 C5 123.6(5) . . ?
F2 C19 F1 103.6(6) . . ?
F2 C19 O3 110.7(6) . . ?
F1 C19 O3 105.9(6) . . ?
C15 C16 C17 120.3(7) . . ?
C16 C15 C14 120.2(7) . . ?
C2 C1 C3 108.5(10) . . ?
C2 C1 C4 110.3(13) . . ?
C3 C1 C4 104.4(9) . . ?
C2 C1 C5 111.0(7) . . ?
C3 C1 C5 114.7(6) . . ?
C4 C1 C5 107.7(7) . . ?
C16 C17 C18 119.6(7) . . ?

_refine_diff_density_max         0.824
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.126

