# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_mo_d8v23103_0m
_database_code_depnum_ccdc_archive 'CCDC 2345379'
loop_
_audit_author_name
_audit_author_address
'Dr. Xuebing Leng'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2024-04-03 deposited with the CCDC.	2024-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Cl F2 N O6 S'
_chemical_formula_weight         369.72

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'
Cl Cl 0.1484 0.1585 '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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   16.5250(5)
_cell_length_b                   12.9543(4)
_cell_length_c                   6.9523(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.0120(10)
_cell_angle_gamma                90
_cell_volume                     1477.15(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    9203
_cell_measurement_theta_min      7.239
_cell_measurement_theta_max      54.966

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.453
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5049
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10261
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.009
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.913
_reflns_number_total             2503
_reflns_number_gt                2449
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_max     0.833
_reflns_Friedel_fraction_full    0.838

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0421P)²+0.5173P] 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     SHELXL
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1083 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.08(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2503
_refine_ls_number_parameters     211
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.002
_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
Cl1 Cl 0.40909(7) 0.85416(8) -0.01642(15) 0.0503(3) Uani 1 1 d . . . . .
S1 S 0.50900(5) 0.70037(5) 0.22276(9) 0.0249(2) Uani 1 1 d . . . . .
F1 F 0.55490(14) 0.88650(17) 0.1280(4) 0.0446(6) Uani 1 1 d . . . . .
F2 F 0.46464(14) 0.89428(16) 0.3288(3) 0.0449(6) Uani 1 1 d . . . . .
O1 O 0.23320(16) 0.5864(2) 0.7997(4) 0.0474(7) Uani 1 1 d . . . . .
O2 O 0.34002(17) 0.5801(2) 1.0147(4) 0.0422(6) Uani 1 1 d . . . . .
O3 O 0.71862(15) 0.7135(2) 0.5450(4) 0.0385(6) Uani 1 1 d . . . . .
O4 O 0.60250(15) 0.80546(17) 0.5313(4) 0.0315(5) Uani 1 1 d . . . . .
O5 O 0.60893(16) 0.5791(2) 0.0140(4) 0.0436(6) Uani 1 1 d . . . . .
O6 O 0.72791(14) 0.61845(19) 0.1887(4) 0.0332(6) Uani 1 1 d . . . . .
N1 N 0.30703(17) 0.5958(2) 0.8505(4) 0.0327(7) Uani 1 1 d . . . . .
C1 C 0.45160(18) 0.6778(2) 0.4217(5) 0.0253(6) Uani 1 1 d . . . . .
C2 C 0.3685(2) 0.7017(3) 0.3950(5) 0.0311(7) Uani 1 1 d . . . . .
H2 H 0.3451 0.7351 0.2817 0.037 Uiso 1 1 calc R U . . .
C3 C 0.3215(2) 0.6752(3) 0.5381(6) 0.0318(7) Uani 1 1 d . . . . .
H3 H 0.2653 0.6899 0.5238 0.038 Uiso 1 1 calc R U . . .
C4 C 0.35799(19) 0.6270(3) 0.7018(5) 0.0272(7) Uani 1 1 d . . . . .
C5 C 0.4403(2) 0.6028(2) 0.7304(5) 0.0277(7) Uani 1 1 d . . . . .
H5 H 0.4635 0.5704 0.8450 0.033 Uiso 1 1 calc R U . . .
C6 C 0.48749(19) 0.6278(2) 0.5855(5) 0.0270(7) Uani 1 1 d . . . . .
H6 H 0.5432 0.6108 0.5986 0.032 Uiso 1 1 calc R U . . .
C7 C 0.4865(2) 0.8436(3) 0.1760(5) 0.0333(8) Uani 1 1 d . . . . .
C8 C 0.60951(18) 0.6844(2) 0.2916(5) 0.0264(7) Uani 1 1 d . . . . .
C9 C 0.65124(19) 0.7334(2) 0.4650(5) 0.0263(7) Uani 1 1 d . . . . .
C10 C 0.6341(3) 0.8559(3) 0.7082(6) 0.0450(10) Uani 1 1 d . . . . .
H10A H 0.6844 0.8913 0.6904 0.067 Uiso 1 1 calc R U . . .
H10B H 0.6447 0.8050 0.8105 0.067 Uiso 1 1 calc R U . . .
H10C H 0.5946 0.9057 0.7435 0.067 Uiso 1 1 calc R U . . .
C11 C 0.6464(2) 0.6224(2) 0.1520(5) 0.0277(7) Uani 1 1 d . . . . .
C12 C 0.7671(2) 0.5575(3) 0.0520(6) 0.0440(9) Uani 1 1 d . . . . .
H12A H 0.7522 0.5841 -0.0779 0.066 Uiso 1 1 calc R U . . .
H12B H 0.7497 0.4862 0.0577 0.066 Uiso 1 1 calc R U . . .
H12C H 0.8258 0.5614 0.0847 0.066 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
Cl1 C7 1.740(4) . ?
S1 C8 1.684(3) . ?
S1 C1 1.794(3) . ?
S1 C7 1.912(3) . ?
F1 C7 1.337(4) . ?
F2 C7 1.336(4) . ?
O1 N1 1.234(4) . ?
O2 N1 1.221(4) . ?
O3 C9 1.210(4) . ?
O4 C9 1.351(4) . ?
O4 C10 1.434(4) . ?
O5 C11 1.214(4) . ?
O6 C11 1.341(4) . ?
O6 C12 1.448(4) . ?
N1 C4 1.468(4) . ?
C1 C6 1.380(5) . ?
C1 C2 1.399(4) . ?
C2 C3 1.378(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.372(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.387(5) . ?
C5 C6 1.385(5) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C8 C11 1.450(5) . ?
C8 C9 1.459(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?

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
C8 S1 C1 110.89(16) . . ?
C8 S1 C7 109.39(16) . . ?
C1 S1 C7 100.33(15) . . ?
C9 O4 C10 116.0(3) . . ?
C11 O6 C12 114.6(3) . . ?
O2 N1 O1 124.4(3) . . ?
O2 N1 C4 118.4(3) . . ?
O1 N1 C4 117.2(3) . . ?
C6 C1 C2 122.0(3) . . ?
C6 C1 S1 119.9(2) . . ?
C2 C1 S1 117.7(3) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 123.1(3) . . ?
C3 C4 N1 118.5(3) . . ?
C5 C4 N1 118.3(3) . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C1 C6 C5 119.1(3) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
F2 C7 F1 108.3(3) . . ?
F2 C7 Cl1 109.1(2) . . ?
F1 C7 Cl1 109.9(3) . . ?
F2 C7 S1 114.0(3) . . ?
F1 C7 S1 107.0(2) . . ?
Cl1 C7 S1 108.43(19) . . ?
C11 C8 C9 126.8(3) . . ?
C11 C8 S1 111.0(2) . . ?
C9 C8 S1 122.1(2) . . ?
O3 C9 O4 122.9(3) . . ?
O3 C9 C8 127.1(3) . . ?
O4 C9 C8 110.0(3) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 C11 O6 122.4(3) . . ?
O5 C11 C8 124.7(3) . . ?
O6 C11 C8 112.9(3) . . ?
O6 C12 H12A 109.5 . . ?
O6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C8 S1 C1 C6 -15.7(3) . . . . ?
C7 S1 C1 C6 -131.2(3) . . . . ?
C8 S1 C1 C2 171.5(3) . . . . ?
C7 S1 C1 C2 55.9(3) . . . . ?
C6 C1 C2 C3 0.7(5) . . . . ?
S1 C1 C2 C3 173.4(3) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C2 C3 C4 N1 -177.9(3) . . . . ?
O2 N1 C4 C3 -159.9(3) . . . . ?
O1 N1 C4 C3 20.7(4) . . . . ?
O2 N1 C4 C5 22.5(4) . . . . ?
O1 N1 C4 C5 -156.9(3) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
N1 C4 C5 C6 176.8(3) . . . . ?
C2 C1 C6 C5 -1.8(5) . . . . ?
S1 C1 C6 C5 -174.3(2) . . . . ?
C4 C5 C6 C1 1.7(5) . . . . ?
C1 S1 C8 C11 133.8(2) . . . . ?
C7 S1 C8 C11 -116.5(2) . . . . ?
C1 S1 C8 C9 -49.5(3) . . . . ?
C7 S1 C8 C9 60.3(3) . . . . ?
C10 O4 C9 O3 -2.0(5) . . . . ?
C10 O4 C9 C8 176.6(3) . . . . ?
C11 C8 C9 O3 -17.5(6) . . . . ?
S1 C8 C9 O3 166.3(3) . . . . ?
C11 C8 C9 O4 164.0(3) . . . . ?
S1 C8 C9 O4 -12.2(4) . . . . ?
C12 O6 C11 O5 -0.7(5) . . . . ?
C12 O6 C11 C8 -179.8(3) . . . . ?
C9 C8 C11 O5 176.5(3) . . . . ?
S1 C8 C11 O5 -6.9(4) . . . . ?
C9 C8 C11 O6 -4.3(5) . . . . ?
S1 C8 C11 O6 172.3(2) . . . . ?

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
C12 H12B O3 0.97 2.64 3.600(5) 172.2 2_564
C5 H5 O5 0.94 2.55 3.225(4) 129.4 1_556
C2 H2 O3 0.94 2.58 3.433(4) 150.5 4_464
C2 H2 Cl1 0.94 2.89 3.606(4) 134.4 .
C12 H12B O3 0.97 2.64 3.600(5) 172.2 2_564
C5 H5 O5 0.94 2.55 3.225(4) 129.4 1_556
C2 H2 O3 0.94 2.58 3.433(4) 150.5 4_464
C2 H2 Cl1 0.94 2.89 3.606(4) 134.4 .
C2 H2 Cl1 0.94 2.89 3.606(4) 134.4 .
C2 H2 O3 0.94 2.58 3.433(4) 150.5 4_464
C5 H5 O5 0.94 2.55 3.225(4) 129.4 1_556
C12 H12B O3 0.97 2.64 3.600(5) 172.2 2_564

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4



