# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_exp_98
_database_code_depnum_ccdc_archive 'CCDC 2070993'
loop_
_audit_author_name
_audit_author_address
'Zhenhua Liu'
;Shandong Normal University
China
;
_audit_update_record             
;
2021-05-18 deposited with the CCDC.	2022-01-05 downloaded from the CCDC.
;
_audit_creation_date             2021-03-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H10 F3 N O2 S'
_chemical_formula_sum            'C10 H10 F3 N O2 S'
_chemical_formula_weight         265.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1'
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'
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'
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.1954(9)
_cell_length_b                   10.2798(9)
_cell_length_c                   8.7100(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.658(7)
_cell_angle_gamma                90.00
_cell_volume                     1173.51(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2272
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5380
_cell_measurement_theta_min      3.5550
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7805
_diffrn_reflns_theta_full        29.25
_diffrn_reflns_theta_max         29.26
_diffrn_reflns_theta_min         3.32
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0793
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.8567
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  51.00   1.00    4.24    --  -18.88  49.00 -52.00   32
  2  ω      6.00  72.00   1.00    4.24    --   19.03  49.00 -52.00   66
  3  ω    -51.00  41.00   1.00    4.24    --   19.03 -49.00 160.00   92
  4  ω    -25.00  11.00   1.00    4.24    --  -18.88 -77.00 -90.00   36
  5  ω    -40.00   5.00   1.00    4.24    --  -18.88 -77.00 120.00   45
  6  ω    -45.00 -10.00   1.00    4.24    --  -18.88  77.00-180.00   35
  7  ω    -41.00   3.00   1.00    4.24    --  -18.88 -77.00  60.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0491061000
_diffrn_orient_matrix_UB_12      0.0242927000
_diffrn_orient_matrix_UB_13      0.0102592000
_diffrn_orient_matrix_UB_21      0.0212353000
_diffrn_orient_matrix_UB_22      0.0340971000
_diffrn_orient_matrix_UB_23      0.0669017000
_diffrn_orient_matrix_UB_31      0.0084775000
_diffrn_orient_matrix_UB_32      0.0548575000
_diffrn_orient_matrix_UB_33      -0.0461611000
_diffrn_oxdiff_digest_frames     
;
019db6439123ebb700e938eef4be75a75a00027a37a
;
_diffrn_oxdiff_digest_hkl        
;
015624ded4f3e4db6ea64367d0e799be1f53ba
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2092
_reflns_number_total             2740
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2740
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0590P)²+0.4790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1349
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), N1(H1)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C1 C 0.38667(14) 0.3748(2) 0.5761(2) 0.0371(4) Uani 1 d . . .
C2 C 0.31660(16) 0.4688(2) 0.6073(3) 0.0442(5) Uani 1 d . . .
H2 H 0.3371 0.5402 0.6688 0.053 Uiso 1 calc . . R
C3 C 0.21573(17) 0.4549(2) 0.5456(3) 0.0517(6) Uani 1 d . . .
H3 H 0.1688 0.5174 0.5685 0.062 Uiso 1 calc . . R
C4 C 0.18200(17) 0.3521(3) 0.4515(3) 0.0525(6) Uani 1 d . . .
C5 C 0.25426(18) 0.2611(2) 0.4190(3) 0.0550(6) Uani 1 d . . .
H5 H 0.2343 0.1916 0.3541 0.066 Uiso 1 calc . . R
C6 C 0.35452(17) 0.2714(2) 0.4805(3) 0.0479(5) Uani 1 d . . .
H6 H 0.4012 0.2086 0.4578 0.057 Uiso 1 calc . . R
C7 C 0.0712(2) 0.3378(3) 0.3868(4) 0.0833(10) Uani 1 d . . .
H7A H 0.0343 0.2964 0.4620 0.125 Uiso 1 calc . . GR
H7B H 0.0664 0.2858 0.2947 0.125 Uiso 1 calc . . GR
H7C H 0.0426 0.4222 0.3625 0.125 Uiso 1 calc . . GR
C8 C 0.53722(15) 0.4605(2) 0.7395(2) 0.0423(5) Uani 1 d . . .
C9 C 0.65200(16) 0.4415(2) 0.7724(2) 0.0439(5) Uani 1 d . . .
H9A H 0.6876 0.5182 0.7418 0.053 Uiso 1 calc . . R
H9B H 0.6734 0.3674 0.7152 0.053 Uiso 1 calc . . R
C10 C 0.81881(19) 0.3967(3) 0.9695(3) 0.0618(7) Uani 1 d . . .
F1 F 0.86213(15) 0.3667(3) 1.1068(2) 0.1235(9) Uani 1 d . . .
F2 F 0.84201(13) 0.3067(2) 0.8740(3) 0.1043(7) Uani 1 d . . .
F3 F 0.85946(13) 0.5061(2) 0.9283(3) 0.1016(7) Uani 1 d . . .
N1 N 0.49085(13) 0.37867(18) 0.6347(2) 0.0422(4) Uani 1 d . . .
H1 H 0.5292 0.3214 0.5986 0.051 Uiso 1 calc . . R
O1 O 0.49549(13) 0.5447(2) 0.8061(2) 0.0726(6) Uani 1 d . . .
O2 O 0.64634(14) 0.28199(16) 1.0066(2) 0.0623(5) Uani 1 d . . .
S1 S 0.68020(4) 0.41445(5) 0.97616(6) 0.04101(18) Uani 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 1.387(3) . ?
C1 C6 1.385(3) . ?
C1 N1 1.411(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(4) . ?
C4 C5 1.388(3) . ?
C4 C7 1.512(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.521(3) . ?
C8 N1 1.336(3) . ?
C8 O1 1.210(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 S1 1.793(2) . ?
C10 F1 1.302(3) . ?
C10 F2 1.304(3) . ?
C10 F3 1.313(3) . ?
C10 S1 1.846(3) . ?
N1 H1 0.8600 . ?
O2 S1 1.4668(17) . ?

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 N1 123.58(19) . . ?
C6 C1 C2 119.21(19) . . ?
C6 C1 N1 117.20(18) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 118.7 . . ?
C4 C3 C2 122.6(2) . . ?
C4 C3 H3 118.7 . . ?
C3 C4 C5 117.1(2) . . ?
C3 C4 C7 121.8(2) . . ?
C5 C4 C7 121.1(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.5(2) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.7 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 114.52(19) . . ?
O1 C8 C9 120.0(2) . . ?
O1 C8 N1 125.5(2) . . ?
C8 C9 H9A 110.3 . . ?
C8 C9 H9B 110.3 . . ?
C8 C9 S1 107.10(14) . . ?
H9A C9 H9B 108.5 . . ?
S1 C9 H9A 110.3 . . ?
S1 C9 H9B 110.3 . . ?
F1 C10 F2 107.9(3) . . ?
F1 C10 F3 107.7(3) . . ?
F1 C10 S1 109.0(2) . . ?
F2 C10 F3 107.4(3) . . ?
F2 C10 S1 113.39(19) . . ?
F3 C10 S1 111.21(19) . . ?
C1 N1 H1 116.0 . . ?
C8 N1 C1 127.96(18) . . ?
C8 N1 H1 116.0 . . ?
C9 S1 C10 94.40(11) . . ?
O2 S1 C9 106.89(11) . . ?
O2 S1 C10 103.75(12) . . ?

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 -1.2(4) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C2 C1 N1 C8 8.0(3) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C2 C3 C4 C7 179.3(2) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
C6 C1 N1 C8 -173.0(2) . . . . ?
C7 C4 C5 C6 -178.3(3) . . . . ?
C8 C9 S1 C10 179.96(17) . . . . ?
C8 C9 S1 O2 74.14(17) . . . . ?
C9 C8 N1 C1 -177.57(19) . . . . ?
F1 C10 S1 C9 -176.0(2) . . . . ?
F1 C10 S1 O2 -67.4(3) . . . . ?
F2 C10 S1 C9 -55.8(2) . . . . ?
F2 C10 S1 O2 52.8(2) . . . . ?
F3 C10 S1 C9 65.4(2) . . . . ?
F3 C10 S1 O2 174.0(2) . . . . ?
N1 C1 C2 C3 -179.1(2) . . . . ?
N1 C1 C6 C5 -180.0(2) . . . . ?
N1 C8 C9 S1 -123.71(18) . . . . ?
O1 C8 C9 S1 56.5(3) . . . . ?
O1 C8 N1 C1 2.2(4) . . . . ?

_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 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.747
