# 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_SB-II-4
_database_code_depnum_ccdc_archive 'CCDC 2234709'
loop_
_audit_author_name
_audit_author_address
' Shiva Prasad Madavi'
;Central University of Tamil Nadu
India
;
_audit_update_record             
;
2023-01-06 deposited with the CCDC.	2023-05-30 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         'C13 H13 F3 N2 O2 S'
_chemical_formula_sum            'C13 H13 F3 N2 O2 S'
_chemical_formula_weight         318.31

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'
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'
F F 0.0171 0.0103 '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'

_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                   10.2811(5)
_cell_length_b                   14.3963(6)
_cell_length_c                   10.3695(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.7220(10)
_cell_angle_gamma                90
_cell_volume                     1370.87(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)


_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      29.54
_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54179
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.830
_diffrn_reflns_theta_max         29.596
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3856
_reflns_number_gt                3081
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'

_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)+(0.0507P)²+0.7095P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3856
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
C1 C 0.41671(17) 0.61177(11) 0.52927(17) 0.0326(3) Uani 1 1 d . . . . .
C2 C 0.4333(2) 0.61095(12) 0.4046(2) 0.0421(4) Uani 1 1 d . . . . .
H2 H 0.512824 0.638857 0.400238 0.051 Uiso 1 1 calc R U . . .
C3 C 0.3254(2) 0.56639(14) 0.28542(19) 0.0479(5) Uani 1 1 d . . . . .
H3 H 0.333256 0.564155 0.199587 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2068(2) 0.52541(14) 0.29149(19) 0.0480(4) Uani 1 1 d . . . . .
H4 H 0.135607 0.497099 0.209539 0.058 Uiso 1 1 calc R U . . .
C5 C 0.1927(2) 0.52599(13) 0.41892(19) 0.0420(4) Uani 1 1 d . . . . .
H5 H 0.113624 0.497781 0.423712 0.050 Uiso 1 1 calc R U . . .
C6 C 0.29942(17) 0.56960(11) 0.53773(16) 0.0319(3) Uani 1 1 d . . . . .
C7 C 0.31725(16) 0.57917(11) 0.68925(16) 0.0309(3) Uani 1 1 d . . . . .
C8 C 0.45997(17) 0.63754(11) 0.76181(17) 0.0341(3) Uani 1 1 d . . . . .
C9 C 0.2254(2) 0.49191(14) 0.8577(2) 0.0503(5) Uani 1 1 d . . . . .
H9A H 0.136506 0.456185 0.808281 0.060 Uiso 1 1 calc R U . . .
H9B H 0.269570 0.475920 0.959458 0.060 Uiso 1 1 calc R U . . .
C10 C 0.1923(2) 0.59536(13) 0.83774(19) 0.0414(4) Uani 1 1 d . . . . .
H10 H 0.093195 0.604477 0.826298 0.050 Uiso 1 1 calc R U . . .
C11 C 0.16353(18) 0.71629(12) 0.65810(19) 0.0374(3) Uani 1 1 d . . . . .
H11A H 0.225209 0.735351 0.614422 0.045 Uiso 1 1 calc R U . . .
H11B H 0.188109 0.754255 0.743206 0.045 Uiso 1 1 calc R U . . .
C12 C 0.0079(2) 0.73225(15) 0.5536(2) 0.0529(5) Uani 1 1 d . . . . .
C13 C 0.6421(2) 0.70338(15) 0.6930(2) 0.0490(5) Uani 1 1 d . . . . .
H13A H 0.681048 0.729481 0.788268 0.073 Uiso 1 1 calc R U . . .
H13B H 0.620149 0.752380 0.623507 0.073 Uiso 1 1 calc R U . . .
H13C H 0.712485 0.662179 0.686740 0.073 Uiso 1 1 calc R U . . .
N1 N 0.50992(15) 0.65205(10) 0.66349(15) 0.0350(3) Uani 1 1 d . . . . .
N2 N 0.19207(14) 0.61900(9) 0.70093(14) 0.0326(3) Uani 1 1 d . . . . .
O1 O 0.51691(14) 0.66536(10) 0.88676(14) 0.0479(3) Uani 1 1 d . . . . .
O2 O 0.28713(19) 0.64949(12) 0.95649(15) 0.0536(4) Uani 1 1 d . . . . .
F1 F -0.08425(16) 0.70689(14) 0.6022(3) 0.1077(7) Uani 1 1 d . . . . .
F2 F -0.01735(16) 0.82196(10) 0.51778(18) 0.0745(4) Uani 1 1 d . . . . .
F3 F -0.0313(2) 0.68663(13) 0.43071(18) 0.1036(7) Uani 1 1 d . . . . .
S1 S 0.34936(6) 0.46726(3) 0.78237(5) 0.04580(14) Uani 1 1 d . . . . .
H2A H 0.366(3) 0.6548(18) 0.958(3) 0.064(8) Uiso 1 1 d . . . . .


_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
C1 C2 1.378(2) . ?
C1 C6 1.388(2) . ?
C1 N1 1.411(2) . ?
C2 C3 1.392(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.504(2) . ?
C7 N2 1.463(2) . ?
C7 C8 1.560(2) . ?
C7 S1 1.8304(16) . ?
C8 O1 1.225(2) . ?
C8 N1 1.348(2) . ?
C9 C10 1.521(3) . ?
C9 S1 1.805(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O2 1.412(2) . ?
C10 N2 1.458(2) . ?
C10 H10 0.9800 . ?
C11 N2 1.459(2) . ?
C11 C12 1.492(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 F1 1.310(3) . ?
C12 F3 1.325(3) . ?
C12 F2 1.337(2) . ?
C13 N1 1.454(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O2 H2A 0.81(3) . ?

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
C2 C1 C6 122.22(16) . . ?
C2 C1 N1 127.82(16) . . ?
C6 C1 N1 109.96(13) . . ?
C1 C2 C3 116.82(17) . . ?
C1 C2 H2 121.6 . . ?
C3 C2 H2 121.6 . . ?
C4 C3 C2 121.63(16) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.76(17) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.04(18) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 120.52(15) . . ?
C5 C6 C7 130.51(15) . . ?
C1 C6 C7 108.95(13) . . ?
N2 C7 C6 115.08(12) . . ?
N2 C7 C8 114.88(13) . . ?
C6 C7 C8 101.51(12) . . ?
N2 C7 S1 104.95(10) . . ?
C6 C7 S1 112.26(11) . . ?
C8 C7 S1 108.20(10) . . ?
O1 C8 N1 125.87(16) . . ?
O1 C8 C7 125.81(15) . . ?
N1 C8 C7 108.32(13) . . ?
C10 C9 S1 106.96(12) . . ?
C10 C9 H9A 110.3 . . ?
S1 C9 H9A 110.3 . . ?
C10 C9 H9B 110.3 . . ?
S1 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
O2 C10 N2 114.71(15) . . ?
O2 C10 C9 113.39(16) . . ?
N2 C10 C9 105.28(14) . . ?
O2 C10 H10 107.7 . . ?
N2 C10 H10 107.7 . . ?
C9 C10 H10 107.7 . . ?
N2 C11 C12 111.85(15) . . ?
N2 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
F1 C12 F3 105.8(2) . . ?
F1 C12 F2 106.99(19) . . ?
F3 C12 F2 105.95(19) . . ?
F1 C12 C11 113.72(19) . . ?
F3 C12 C11 112.68(18) . . ?
F2 C12 C11 111.20(17) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 N1 C1 111.19(13) . . ?
C8 N1 C13 123.89(15) . . ?
C1 N1 C13 124.92(15) . . ?
C10 N2 C11 115.62(14) . . ?
C10 N2 C7 111.88(13) . . ?
C11 N2 C7 114.53(13) . . ?
C10 O2 H2A 111.3(19) . . ?
C9 S1 C7 93.46(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
C6 C1 C2 C3 0.7(2) . . . . ?
N1 C1 C2 C3 -179.93(16) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 -177.80(17) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
N1 C1 C6 C5 179.51(15) . . . . ?
C2 C1 C6 C7 177.41(15) . . . . ?
N1 C1 C6 C7 -2.07(17) . . . . ?
C5 C6 C7 N2 -54.6(2) . . . . ?
C1 C6 C7 N2 127.20(14) . . . . ?
C5 C6 C7 C8 -179.29(17) . . . . ?
C1 C6 C7 C8 2.49(16) . . . . ?
C5 C6 C7 S1 65.4(2) . . . . ?
C1 C6 C7 S1 -112.84(13) . . . . ?
N2 C7 C8 O1 53.1(2) . . . . ?
C6 C7 C8 O1 177.91(17) . . . . ?
S1 C7 C8 O1 -63.80(19) . . . . ?
N2 C7 C8 N1 -126.98(14) . . . . ?
C6 C7 C8 N1 -2.14(16) . . . . ?
S1 C7 C8 N1 116.15(12) . . . . ?
S1 C9 C10 O2 -91.64(16) . . . . ?
S1 C9 C10 N2 34.54(18) . . . . ?
N2 C11 C12 F1 57.8(2) . . . . ?
N2 C11 C12 F3 -62.6(2) . . . . ?
N2 C11 C12 F2 178.61(16) . . . . ?
O1 C8 N1 C1 -178.99(16) . . . . ?
C7 C8 N1 C1 1.06(18) . . . . ?
O1 C8 N1 C13 0.5(3) . . . . ?
C7 C8 N1 C13 -179.46(15) . . . . ?
C2 C1 N1 C8 -178.83(16) . . . . ?
C6 C1 N1 C8 0.61(18) . . . . ?
C2 C1 N1 C13 1.7(3) . . . . ?
C6 C1 N1 C13 -178.86(16) . . . . ?
O2 C10 N2 C11 -54.2(2) . . . . ?
C9 C10 N2 C11 -179.53(14) . . . . ?
O2 C10 N2 C7 79.37(18) . . . . ?
C9 C10 N2 C7 -45.99(18) . . . . ?
C12 C11 N2 C10 -97.82(18) . . . . ?
C12 C11 N2 C7 129.87(16) . . . . ?
C6 C7 N2 C10 158.74(14) . . . . ?
C8 C7 N2 C10 -83.87(16) . . . . ?
S1 C7 N2 C10 34.83(15) . . . . ?
C6 C7 N2 C11 -67.19(17) . . . . ?
C8 C7 N2 C11 50.20(17) . . . . ?
S1 C7 N2 C11 168.90(11) . . . . ?
C10 C9 S1 C7 -13.68(15) . . . . ?
N2 C7 S1 C9 -10.75(12) . . . . ?
C6 C7 S1 C9 -136.44(13) . . . . ?
C8 C7 S1 C9 112.36(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
C11 H11A O2 0.97 2.60 3.480(2) 150.5 4_575 yes
C13 H13B O1 0.96 2.49 3.411(2) 160.2 4_575 yes
O2 H2A O1 0.81(3) 2.00(3) 2.774(2) 160(3) . yes

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.053

