# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_KPunjajom01_Sarpong
_database_code_depnum_ccdc_archive 'CCDC 2284144'
loop_
_audit_author_name
_audit_author_address
'Nicholas Settineri'
;UC Berkeley Small Molecule Xray Crystallography Facility
United States of America
;
_audit_update_record             
;
2023-07-24 deposited with the CCDC.	2023-11-27 downloaded from the CCDC.
;
_audit_creation_date             2022-09-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 F N2 O2 S'
_chemical_formula_sum            'C12 H13 F N2 O2 S'
_chemical_formula_weight         268.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C F O S N H'
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'
S S 0.3331 0.5567 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   21.5943(5)
_cell_length_b                   5.87350(10)
_cell_length_c                   9.8361(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.575(2)
_cell_angle_gamma                90
_cell_volume                     1226.36(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6963
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.1730
_cell_measurement_theta_min      6.2380
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.741
_exptl_absorpt_coefficient_mu    2.449
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13506
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.464
_diffrn_reflns_theta_min         4.165
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  27.00   0.50    1.00    --  -50.71  37.00 -49.00  144
  2  ω   -128.00 -39.00   0.50    1.00    --  -50.71 -37.00 154.00  178
  3  ω     39.00 128.00   0.50    1.00    --   50.71  37.00 -49.00  178
  4  ω    -27.00  39.00   0.50    1.00    --   50.71 -37.00 154.00  132
  5  ω   -178.00 -87.00   0.50    4.00    -- -100.00 -37.00 154.00  182
  6  ω     95.00 175.00   0.50    4.00    --  107.75  37.00 -49.00  160
  7  ω    -30.00  29.00   0.50    1.00    --  -50.71  19.00  90.00  118
  8  ω     76.00 124.00   0.50    1.00    --   50.71 125.00   0.00   96
  9  ω     81.00 124.00   0.50    1.00    --   50.71  77.00-120.00   86
 10  ω    -28.00  24.00   0.50    1.00    --   50.71 -19.00   0.00  104
 11  ω     81.00 124.00   0.50    1.00    --   50.71  77.00  90.00   86
 12  ω   -108.00 -26.00   0.50    4.00    -- -100.00  77.00 -60.00  164
 13  ω    -54.00 -24.00   0.50    4.00    -- -100.00  45.00-120.00   60
 14  ω    -74.00 -29.00   0.50    4.00    -- -100.00  61.00  60.00   90
 15  ω     36.00  68.00   0.50    4.00    --  107.75 -61.00-150.00   64
 16  ω     34.00 102.00   0.50    4.00    --  107.75 -77.00-180.00  136
 17  ω     36.00  68.00   0.50    4.00    --  107.75 -61.00 150.00   64
 18  ω     83.00 175.00   0.50    4.00    --  107.75 111.00  60.00  184
 19  ω     34.00 102.00   0.50    4.00    --  107.75 -77.00 150.00  136
 20  ω     35.00 109.00   0.50    4.00    --  107.75-111.00  60.00  148
 21  ω     36.00  68.00   0.50    4.00    --  107.75 -61.00-120.00   64
 22  ω     34.00 102.00   0.50    4.00    --  107.75 -77.00  90.00  136
 23  ω     94.00 175.00   0.50    4.00    --  107.75  30.00 -90.00  162
 24  ω     94.00 175.00   0.50    4.00    --  107.75  45.00 -30.00  162
 25  ω     34.00 102.00   0.50    4.00    --  107.75 -77.00 -30.00  136
 26  ω     34.00  83.00   0.50    4.00    --  107.75 -77.00  60.00   98
 27  ω     31.00  83.00   0.50    4.00    --  107.75 -94.00 -30.00  104
 28  ω     36.00  68.00   0.50    4.00    --  107.75 -61.00-180.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0695960000
_diffrn_orient_matrix_UB_12      0.0734293000
_diffrn_orient_matrix_UB_13      0.0337798000
_diffrn_orient_matrix_UB_21      -0.0053407000
_diffrn_orient_matrix_UB_22      0.0977273000
_diffrn_orient_matrix_UB_23      -0.1470517000
_diffrn_orient_matrix_UB_31      -0.0197808000
_diffrn_orient_matrix_UB_32      0.2322021000
_diffrn_orient_matrix_UB_33      0.0511577000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2198
_reflns_number_total             2513
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.065
_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)+(0.0614P)²+0.4970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1089
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12)
2.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.22419(2) 0.69129(7) 0.71607(4) 0.02005(15) Uani 1 1 d . . . . .
F1 F 0.48248(5) 0.4681(2) 0.26065(12) 0.0351(3) Uani 1 1 d . . . . .
O1 O 0.19717(6) 0.9147(2) 0.70906(13) 0.0269(3) Uani 1 1 d . . . . .
O2 O 0.23412(6) 0.5857(2) 0.84994(11) 0.0260(3) Uani 1 1 d . . . . .
N1 N 0.18493(7) 0.5294(3) 0.59357(14) 0.0218(3) Uani 1 1 d . . . . .
N2 N 0.29115(7) 0.6952(3) 0.65729(14) 0.0224(3) Uani 1 1 d . . . . .
C1 C 0.07512(9) 0.1133(4) 0.47136(19) 0.0301(4) Uani 1 1 d . . . . .
H1A H 0.0492 0.0624 0.3882 0.036 Uiso 1 1 calc R U . . .
H1B H 0.0918 0.0067 0.5412 0.036 Uiso 1 1 calc R U . . .
C2 C 0.08792(8) 0.3320(3) 0.48986(17) 0.0226(4) Uani 1 1 d . . . . .
C3 C 0.06347(9) 0.5109(4) 0.38479(19) 0.0294(4) Uani 1 1 d . . . . .
H3A H 0.0345 0.6116 0.4220 0.044 Uiso 1 1 calc R U . . .
H3B H 0.0412 0.4377 0.3003 0.044 Uiso 1 1 calc R U . . .
H3C H 0.0988 0.6002 0.3634 0.044 Uiso 1 1 calc R U . . .
C4 C 0.12839(8) 0.4136(3) 0.62296(16) 0.0223(4) Uani 1 1 d . . . . .
H4A H 0.1039 0.5199 0.6706 0.027 Uiso 1 1 calc R U . . .
H4B H 0.1410 0.2822 0.6849 0.027 Uiso 1 1 calc R U . . .
C5 C 0.23006(8) 0.4007(3) 0.52963(16) 0.0214(4) Uani 1 1 d . . . . .
H5A H 0.2154 0.3864 0.4285 0.026 Uiso 1 1 calc R U . . .
H5B H 0.2370 0.2467 0.5705 0.026 Uiso 1 1 calc R U . . .
C6 C 0.28921(8) 0.5426(3) 0.56197(16) 0.0205(4) Uani 1 1 d . . . . .
C7 C 0.34167(8) 0.5155(3) 0.48689(16) 0.0211(4) Uani 1 1 d . . . . .
C8 C 0.34494(8) 0.3252(3) 0.40347(18) 0.0249(4) Uani 1 1 d . . . . .
H8 H 0.3142 0.2083 0.3981 0.030 Uiso 1 1 calc R U . . .
C9 C 0.39344(9) 0.3069(3) 0.32795(19) 0.0277(4) Uani 1 1 d . . . . .
H9 H 0.3968 0.1774 0.2719 0.033 Uiso 1 1 calc R U . . .
C10 C 0.43618(8) 0.4817(4) 0.33708(18) 0.0267(4) Uani 1 1 d . . . . .
C11 C 0.43484(9) 0.6711(3) 0.41987(19) 0.0275(4) Uani 1 1 d . . . . .
H11 H 0.4658 0.7870 0.4246 0.033 Uiso 1 1 calc R U . . .
C12 C 0.38700(8) 0.6868(3) 0.49565(18) 0.0246(4) Uani 1 1 d . . . . .
H12 H 0.3850 0.8147 0.5538 0.030 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 O1 1.4326(13) . ?
S1 O2 1.4357(12) . ?
S1 N1 1.6430(14) . ?
S1 N2 1.6530(15) . ?
F1 C10 1.3591(19) . ?
N1 C4 1.472(2) . ?
N1 C5 1.464(2) . ?
N2 C6 1.292(2) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C1 C2 1.320(3) . ?
C2 C3 1.500(3) . ?
C2 C4 1.512(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.509(2) . ?
C6 C7 1.470(2) . ?
C7 C8 1.396(3) . ?
C7 C12 1.395(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.395(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.372(3) . ?
C10 C11 1.382(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9500 . ?

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
O1 S1 O2 115.53(8) . . ?
O1 S1 N1 110.12(8) . . ?
O1 S1 N2 110.19(8) . . ?
O2 S1 N1 113.12(8) . . ?
O2 S1 N2 109.49(7) . . ?
N1 S1 N2 96.79(7) . . ?
C4 N1 S1 117.28(11) . . ?
C5 N1 S1 108.63(11) . . ?
C5 N1 C4 119.17(14) . . ?
C6 N2 S1 109.29(12) . . ?
H1A C1 H1B 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
C1 C2 C3 123.26(17) . . ?
C1 C2 C4 120.05(16) . . ?
C3 C2 C4 116.68(16) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C2 110.17(13) . . ?
N1 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
C2 C4 H4A 109.6 . . ?
C2 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
N1 C5 H5A 111.1 . . ?
N1 C5 H5B 111.1 . . ?
N1 C5 C6 103.22(14) . . ?
H5A C5 H5B 109.1 . . ?
C6 C5 H5A 111.1 . . ?
C6 C5 H5B 111.1 . . ?
N2 C6 C5 116.70(15) . . ?
N2 C6 C7 120.95(15) . . ?
C7 C6 C5 122.32(15) . . ?
C8 C7 C6 120.57(16) . . ?
C12 C7 C6 119.18(16) . . ?
C12 C7 C8 120.21(16) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.91(17) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 117.98(17) . . ?
C10 C9 H9 121.0 . . ?
F1 C10 C9 118.30(17) . . ?
F1 C10 C11 118.06(17) . . ?
C9 C10 C11 123.65(17) . . ?
C10 C11 H11 121.0 . . ?
C10 C11 C12 118.02(17) . . ?
C12 C11 H11 121.0 . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.22(17) . . ?
C11 C12 H12 119.9 . . ?

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
S1 N1 C4 C2 163.16(12) . . . . ?
S1 N1 C5 C6 -22.88(15) . . . . ?
S1 N2 C6 C5 -1.02(19) . . . . ?
S1 N2 C6 C7 177.22(12) . . . . ?
F1 C10 C11 C12 178.81(15) . . . . ?
O1 S1 N1 C4 -85.19(14) . . . . ?
O1 S1 N1 C5 135.99(11) . . . . ?
O1 S1 N2 C6 -126.56(12) . . . . ?
O2 S1 N1 C4 45.77(15) . . . . ?
O2 S1 N1 C5 -93.05(12) . . . . ?
O2 S1 N2 C6 105.32(13) . . . . ?
N1 S1 N2 C6 -12.17(13) . . . . ?
N1 C5 C6 N2 15.65(19) . . . . ?
N1 C5 C6 C7 -162.56(14) . . . . ?
N2 S1 N1 C4 160.37(13) . . . . ?
N2 S1 N1 C5 21.55(12) . . . . ?
N2 C6 C7 C8 167.84(16) . . . . ?
N2 C6 C7 C12 -14.6(2) . . . . ?
C1 C2 C4 N1 120.34(18) . . . . ?
C3 C2 C4 N1 -60.43(19) . . . . ?
C4 N1 C5 C6 -160.79(13) . . . . ?
C5 N1 C4 C2 -62.45(19) . . . . ?
C5 C6 C7 C8 -14.0(2) . . . . ?
C5 C6 C7 C12 163.50(16) . . . . ?
C6 C7 C8 C9 177.09(15) . . . . ?
C6 C7 C12 C11 -176.41(16) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C8 C7 C12 C11 1.1(3) . . . . ?
C8 C9 C10 F1 -178.11(15) . . . . ?
C8 C9 C10 C11 2.0(3) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C7 -0.3(3) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.000
_oxdiff_exptl_absorpt_empirical_full_min 0.559
