# 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_mo_d8v21634_0m
_database_code_depnum_ccdc_archive 'CCDC 2114753'
loop_
_audit_author_name
_audit_author_address
'Xiaoyu Ma'
;Shanghai Institute of Technology 
China
;
_audit_update_record             
;
2021-10-09 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 F2 O2 S'
_chemical_formula_weight         282.30

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'
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 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.1569(6)
_cell_length_b                   7.4390(7)
_cell_length_c                   28.410(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.592(3)
_cell_angle_gamma                90
_cell_volume                     1297.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6966
_cell_measurement_theta_min      5.662
_cell_measurement_theta_max      54.775

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.268
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5985
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            20165
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.831
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2539
_reflns_number_gt                1911
_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       '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)+(0.0854P)²+0.6279P] 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       0.016(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2539
_refine_ls_number_parameters     174
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1815
_refine_ls_wR_factor_gt          0.1645
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.073
_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
S1 S 0.53208(19) 0.17967(16) 0.71183(3) 0.0972(4) Uani 1 1 d . U . . .
F1 F 0.6247(2) 0.3709(3) 0.52787(6) 0.0735(5) Uani 1 1 d . . . . .
F2 F 0.5295(5) 0.2172(4) 0.76317(7) 0.1360(11) Uani 1 1 d . . . . .
O1 O 0.7434(5) 0.1885(6) 0.69810(10) 0.1395(14) Uani 1 1 d . U . . .
O2 O 0.4248(7) 0.0103(4) 0.70214(10) 0.1344(12) Uani 1 1 d . U . . .
C1 C 0.3925(5) 0.1591(4) 0.45490(9) 0.0600(7) Uani 1 1 d . . . . .
H1 H 0.5276 0.1265 0.4694 0.072 Uiso 1 1 calc R U . . .
C2 C 0.3512(6) 0.1372(4) 0.40683(10) 0.0710(8) Uani 1 1 d . . . . .
H2 H 0.4583 0.0897 0.3891 0.085 Uiso 1 1 calc R U . . .
C3 C 0.1522(6) 0.1853(4) 0.38492(10) 0.0776(9) Uani 1 1 d . . . . .
H3 H 0.1240 0.1688 0.3526 0.093 Uiso 1 1 calc R U . . .
C4 C -0.0044(6) 0.2576(5) 0.41099(11) 0.0757(9) Uani 1 1 d . . . . .
H4 H -0.1376 0.2926 0.3960 0.091 Uiso 1 1 calc R U . . .
C5 C 0.0338(5) 0.2790(4) 0.45903(10) 0.0613(7) Uani 1 1 d . . . . .
H5 H -0.0744 0.3266 0.4764 0.074 Uiso 1 1 calc R U . . .
C6 C 0.2340(4) 0.2295(3) 0.48190(9) 0.0513(6) Uani 1 1 d . . . . .
C7 C 0.2718(4) 0.2550(3) 0.53377(8) 0.0499(6) Uani 1 1 d . . . . .
C8 C 0.1147(4) 0.2103(4) 0.56427(9) 0.0571(7) Uani 1 1 d . . . . .
H8 H -0.0155 0.1592 0.5519 0.069 Uiso 1 1 calc R U . . .
C9 C 0.1452(5) 0.2390(4) 0.61233(10) 0.0611(7) Uani 1 1 d . . . . .
H9 H 0.0367 0.2065 0.6316 0.073 Uiso 1 1 calc R U . . .
C10 C 0.3355(4) 0.3158(4) 0.63197(9) 0.0573(7) Uani 1 1 d . . . . .
C11 C 0.4961(4) 0.3608(4) 0.60268(9) 0.0582(7) Uani 1 1 d . . . . .
H11 H 0.6254 0.4130 0.6152 0.070 Uiso 1 1 calc R U . . .
C12 C 0.4634(4) 0.3279(3) 0.55514(9) 0.0523(6) Uani 1 1 d . . . . .
C13 C 0.3634(5) 0.3520(4) 0.68484(10) 0.0714(8) Uani 1 1 d . . . . .
H13 H 0.2195 0.3403 0.6970 0.086 Uiso 1 1 calc R U . . .
C14 C 0.4494(8) 0.5350(6) 0.69877(14) 0.1058(13) Uani 1 1 d . . . . .
H14A H 0.4502 0.5489 0.7324 0.159 Uiso 1 1 calc R U . . .
H14B H 0.3579 0.6254 0.6834 0.159 Uiso 1 1 calc R U . . .
H14C H 0.5951 0.5477 0.6894 0.159 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 1.390(3) . ?
S1 O2 1.439(4) . ?
S1 F2 1.486(2) . ?
S1 C13 1.784(3) . ?
F1 C12 1.346(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.391(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(3) . ?
C7 C8 1.390(4) . ?
C7 C12 1.393(3) . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(4) . ?
C10 C13 1.522(4) . ?
C11 C12 1.372(3) . ?
C11 H11 0.9300 . ?
C13 C14 1.502(5) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 114.4(2) . . ?
O1 S1 F2 110.52(19) . . ?
O2 S1 F2 108.1(2) . . ?
O1 S1 C13 111.81(19) . . ?
O2 S1 C13 107.74(19) . . ?
F2 S1 C13 103.60(15) . . ?
C2 C1 C6 120.6(3) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.3(2) . . ?
C1 C6 C7 122.3(2) . . ?
C5 C6 C7 119.4(2) . . ?
C8 C7 C12 115.4(2) . . ?
C8 C7 C6 121.8(2) . . ?
C12 C7 C6 122.8(2) . . ?
C9 C8 C7 122.2(2) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 118.8(2) . . ?
C9 C10 C13 119.8(2) . . ?
C11 C10 C13 121.4(2) . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
F1 C12 C11 117.9(2) . . ?
F1 C12 C7 118.7(2) . . ?
C11 C12 C7 123.4(2) . . ?
C14 C13 C10 115.5(3) . . ?
C14 C13 S1 110.9(2) . . ?
C10 C13 S1 108.2(2) . . ?
C14 C13 H13 107.3 . . ?
C10 C13 H13 107.3 . . ?
S1 C13 H13 107.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C6 C1 C2 C3 0.2(4) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C1 C6 C7 179.9(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 179.6(3) . . . . ?
C1 C6 C7 C8 -137.1(3) . . . . ?
C5 C6 C7 C8 43.5(3) . . . . ?
C1 C6 C7 C12 44.1(4) . . . . ?
C5 C6 C7 C12 -135.3(3) . . . . ?
C12 C7 C8 C9 1.1(4) . . . . ?
C6 C7 C8 C9 -177.8(2) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C8 C9 C10 C13 178.1(3) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C13 C10 C11 C12 -179.2(2) . . . . ?
C10 C11 C12 F1 -179.0(2) . . . . ?
C10 C11 C12 C7 1.9(4) . . . . ?
C8 C7 C12 F1 178.6(2) . . . . ?
C6 C7 C12 F1 -2.5(4) . . . . ?
C8 C7 C12 C11 -2.3(4) . . . . ?
C6 C7 C12 C11 176.5(2) . . . . ?
C9 C10 C13 C14 -133.3(3) . . . . ?
C11 C10 C13 C14 45.7(4) . . . . ?
C9 C10 C13 S1 101.7(3) . . . . ?
C11 C10 C13 S1 -79.3(3) . . . . ?
O1 S1 C13 C14 -61.1(3) . . . . ?
O2 S1 C13 C14 172.4(3) . . . . ?
F2 S1 C13 C14 58.0(3) . . . . ?
O1 S1 C13 C10 66.6(3) . . . . ?
O2 S1 C13 C10 -60.0(3) . . . . ?
F2 S1 C13 C10 -174.4(2) . . . . ?

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

