# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20211125fL_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2125051'
loop_
_audit_author_name
_audit_author_address
Ms
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2021-11-29 deposited with the CCDC.	2023-07-17 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            'C9 H9 F3 O4 S2'
_chemical_formula_weight         302.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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                   24.794(10)
_cell_length_b                   5.2770(9)
_cell_length_c                   9.1654(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.193(16)
_cell_angle_gamma                90
_cell_volume                     1198.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.949
_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      115(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13080
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.104
_diffrn_reflns_theta_max         55.029
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2264
_reflns_number_gt                2076
_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 2014/5 (Sheldrick, 2014)'
_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)+(0.0835P)²+4.1279P] 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         2264
_refine_ls_number_parameters     174
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.1745
_refine_ls_wR_factor_gt          0.1707
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.157
_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
S001 S 0.91066(3) 0.60362(16) 0.41262(8) 0.0161(3) Uani 1 1 d . . . . .
S002 S 0.63298(5) 0.6388(2) 0.31276(14) 0.0328(4) Uani 0.893(4) 1 d D U P A 1
O003 O 0.91772(10) 0.4868(5) 0.5549(3) 0.0234(6) Uani 1 1 d . . . . .
O004 O 0.91677(10) 0.8743(5) 0.4034(3) 0.0243(6) Uani 1 1 d . . . . .
O005 O 0.64835(12) 0.3492(6) 0.2848(3) 0.0341(7) Uani 1 1 d D U . . .
F006 F 0.54555(13) 0.7461(8) 0.4474(4) 0.0695(10) Uani 1 1 d . U . . .
O007 O 0.66506(13) 0.7331(7) 0.4392(4) 0.0491(9) Uani 1 1 d . U . . .
F008 F 0.57764(14) 0.3842(8) 0.5055(4) 0.0740(11) Uani 1 1 d . U . . .
F009 F 0.53637(12) 0.4432(10) 0.2948(4) 0.0882(14) Uani 1 1 d . U . . .
C00A C 0.74409(15) 0.3913(7) 0.2323(4) 0.0220(8) Uani 1 1 d . . . . .
C00B C 0.84511(13) 0.5241(7) 0.3437(3) 0.0162(7) Uani 1 1 d . . . . .
C00C C 0.82108(14) 0.6730(7) 0.2348(4) 0.0197(7) Uani 1 1 d . . . . .
H00C H 0.839191 0.816943 0.198218 0.024 Uiso 1 1 calc R U . . .
C00D C 0.81978(14) 0.3102(7) 0.3990(4) 0.0217(8) Uani 1 1 d . . . . .
H00D H 0.836962 0.211555 0.473944 0.026 Uiso 1 1 calc R U . . .
C00E C 0.76930(14) 0.2450(7) 0.3424(4) 0.0226(8) Uani 1 1 d . . . . .
H00E H 0.751538 0.099697 0.378527 0.027 Uiso 1 1 calc R U . . .
C00F C 0.76979(15) 0.6068(7) 0.1803(4) 0.0214(8) Uani 1 1 d . . . . .
H00F H 0.752232 0.708591 0.107389 0.026 Uiso 1 1 calc R U . . .
C00G C 0.95306(14) 0.4531(7) 0.2907(4) 0.0202(7) Uani 1 1 d . . . . .
H00A H 0.990819 0.483124 0.321405 0.030 Uiso 1 1 calc R U . . .
H00B H 0.946261 0.521432 0.192322 0.030 Uiso 1 1 calc R U . . .
H00G H 0.945808 0.270508 0.290327 0.030 Uiso 1 1 calc R U . . .
C00H C 0.68910(15) 0.3150(8) 0.1737(4) 0.0279(8) Uani 1 1 d . U . . .
H00H H 0.679210 0.418870 0.086778 0.034 Uiso 1 1 calc R U . . .
H00I H 0.689794 0.135109 0.143124 0.034 Uiso 1 1 calc R U . . .
C00I C 0.56891(19) 0.5485(12) 0.3925(6) 0.0493(9) Uani 1 1 d D U . . .
S1 S 0.6386(3) 0.520(3) 0.3921(14) 0.045(2) Uani 0.107(4) 1 d D U P A 2


_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
S001 O004 1.439(3) . ?
S001 O003 1.447(2) . ?
S001 C00G 1.753(3) . ?
S001 C00B 1.771(3) . ?
S002 O007 1.467(3) . ?
S002 O005 1.598(3) . ?
S002 C00I 1.837(5) . ?
O005 S1 1.362(11) . ?
O005 C00H 1.473(5) . ?
F006 C00I 1.303(7) . ?
O007 S1 1.365(12) . ?
F008 C00I 1.362(7) . ?
F009 C00I 1.306(6) . ?
C00A C00F 1.396(5) . ?
C00A C00E 1.399(5) . ?
C00A C00H 1.501(5) . ?
C00B C00C 1.387(5) . ?
C00B C00D 1.396(5) . ?
C00C C00F 1.393(5) . ?
C00C H00C 0.9500 . ?
C00D C00E 1.380(5) . ?
C00D H00D 0.9500 . ?
C00E H00E 0.9500 . ?
C00F H00F 0.9500 . ?
C00G H00A 0.9800 . ?
C00G H00B 0.9800 . ?
C00G H00G 0.9800 . ?
C00H H00H 0.9900 . ?
C00H H00I 0.9900 . ?
C00I S1 1.734(9) . ?

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
O004 S001 O003 117.79(16) . . ?
O004 S001 C00G 110.20(17) . . ?
O003 S001 C00G 109.05(16) . . ?
O004 S001 C00B 108.15(16) . . ?
O003 S001 C00B 107.34(16) . . ?
C00G S001 C00B 103.29(16) . . ?
O007 S002 O005 109.0(2) . . ?
O007 S002 C00I 103.0(2) . . ?
O005 S002 C00I 91.8(2) . . ?
S1 O005 C00H 136.6(5) . . ?
C00H O005 S002 113.7(3) . . ?
C00F C00A C00E 119.9(3) . . ?
C00F C00A C00H 121.1(3) . . ?
C00E C00A C00H 119.0(3) . . ?
C00C C00B C00D 122.2(3) . . ?
C00C C00B S001 119.0(3) . . ?
C00D C00B S001 118.8(3) . . ?
C00B C00C C00F 118.5(3) . . ?
C00B C00C H00C 120.8 . . ?
C00F C00C H00C 120.8 . . ?
C00E C00D C00B 118.7(3) . . ?
C00E C00D H00D 120.7 . . ?
C00B C00D H00D 120.7 . . ?
C00D C00E C00A 120.5(3) . . ?
C00D C00E H00E 119.8 . . ?
C00A C00E H00E 119.8 . . ?
C00C C00F C00A 120.3(3) . . ?
C00C C00F H00F 119.9 . . ?
C00A C00F H00F 119.9 . . ?
S001 C00G H00A 109.5 . . ?
S001 C00G H00B 109.5 . . ?
H00A C00G H00B 109.5 . . ?
S001 C00G H00G 109.5 . . ?
H00A C00G H00G 109.5 . . ?
H00B C00G H00G 109.5 . . ?
O005 C00H C00A 110.9(3) . . ?
O005 C00H H00H 109.5 . . ?
C00A C00H H00H 109.5 . . ?
O005 C00H H00I 109.5 . . ?
C00A C00H H00I 109.5 . . ?
H00H C00H H00I 108.0 . . ?
F006 C00I F009 109.5(4) . . ?
F006 C00I F008 106.0(4) . . ?
F009 C00I F008 109.1(5) . . ?
F006 C00I S1 121.9(6) . . ?
F009 C00I S1 123.4(5) . . ?
F008 C00I S1 79.4(6) . . ?
F006 C00I S002 110.5(4) . . ?
F009 C00I S002 111.0(4) . . ?
F008 C00I S002 110.7(3) . . ?
O005 S1 O007 132.6(8) . . ?
O005 S1 C00I 105.3(6) . . ?
O007 S1 C00I 113.3(7) . . ?

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
O007 S002 O005 C00H -96.1(3) . . . . ?
C00I S002 O005 C00H 159.6(3) . . . . ?
O004 S001 C00B C00C 31.0(3) . . . . ?
O003 S001 C00B C00C 159.0(3) . . . . ?
C00G S001 C00B C00C -85.8(3) . . . . ?
O004 S001 C00B C00D -150.3(3) . . . . ?
O003 S001 C00B C00D -22.3(3) . . . . ?
C00G S001 C00B C00D 92.9(3) . . . . ?
C00D C00B C00C C00F 0.6(5) . . . . ?
S001 C00B C00C C00F 179.2(3) . . . . ?
C00C C00B C00D C00E 0.3(5) . . . . ?
S001 C00B C00D C00E -178.4(3) . . . . ?
C00B C00D C00E C00A -0.2(5) . . . . ?
C00F C00A C00E C00D -0.8(5) . . . . ?
C00H C00A C00E C00D -179.9(3) . . . . ?
C00B C00C C00F C00A -1.6(5) . . . . ?
C00E C00A C00F C00C 1.7(5) . . . . ?
C00H C00A C00F C00C -179.3(3) . . . . ?
S1 O005 C00H C00A 37.3(10) . . . . ?
S002 O005 C00H C00A 73.8(4) . . . . ?
C00F C00A C00H O005 -111.0(4) . . . . ?
C00E C00A C00H O005 68.1(5) . . . . ?
O007 S002 C00I F006 62.6(4) . . . . ?
O005 S002 C00I F006 172.6(4) . . . . ?
O007 S002 C00I F009 -175.7(4) . . . . ?
O005 S002 C00I F009 -65.8(5) . . . . ?
O007 S002 C00I F008 -54.5(4) . . . . ?
O005 S002 C00I F008 55.5(4) . . . . ?
C00H O005 S1 O007 -1(2) . . . . ?
C00H O005 S1 C00I 143.1(5) . . . . ?
F006 C00I S1 O005 -158.5(7) . . . . ?
F009 C00I S1 O005 -6.9(13) . . . . ?
F008 C00I S1 O005 99.1(9) . . . . ?
F006 C00I S1 O007 -6.8(13) . . . . ?
F009 C00I S1 O007 144.9(8) . . . . ?
F008 C00I S1 O007 -109.2(9) . . . . ?

_refine_diff_density_max         1.301
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.110

