# 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 
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data_mo_211008_sj_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2114772'
_audit_update_record             
;
2021-10-09 deposited with the CCDC.	2021-12-13 downloaded from the CCDC.
;
_audit_creation_date             2021-10-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 F3 O2 S'
_chemical_formula_sum            'C16 H11 F3 O2 S'
_chemical_formula_weight         324.31
_chemical_melting_point          ?
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'

_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                   15.060(7)
_cell_length_b                   5.814(3)
_cell_length_c                   17.346(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.484(18)
_cell_angle_gamma                90
_cell_volume                     1382.2(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.880
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1498 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.9274.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22040
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.117
_diffrn_reflns_theta_min         2.385
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2705
_reflns_number_total             3064
_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       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+0.5625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0735
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C15(H15), C16(H16)
;
_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 0.37642(2) 0.86621(6) 0.48948(2) 0.03212(10) Uani 1 1 d . . . . .
F1 F 0.30113(6) 0.49043(13) 0.52151(5) 0.03505(19) Uani 1 1 d . . . . .
F2 F 0.29005(6) 0.79148(16) 0.59039(5) 0.0368(2) Uani 1 1 d . . . . .
F3 F 0.71030(6) 0.80368(17) 0.82016(5) 0.0459(2) Uani 1 1 d . . . . .
O1 O 0.10535(7) 0.32557(16) 0.38091(6) 0.0305(2) Uani 1 1 d . . . . .
O2 O 0.08593(7) 0.25064(19) 0.49696(7) 0.0413(3) Uani 1 1 d . . . . .
C1 C 0.10082(9) 0.4133(2) 0.24671(8) 0.0299(3) Uani 1 1 d . . . . .
H1 H 0.071874 0.267011 0.227864 0.036 Uiso 1 1 calc R . . . .
C2 C 0.12034(10) 0.5578(3) 0.19232(8) 0.0321(3) Uani 1 1 d . . . . .
H2 H 0.105254 0.510469 0.135852 0.038 Uiso 1 1 calc R . . . .
C3 C 0.16195(10) 0.7721(2) 0.22020(8) 0.0319(3) Uani 1 1 d . . . . .
H3 H 0.175689 0.871055 0.182939 0.038 Uiso 1 1 calc R . . . .
C4 C 0.18348(9) 0.8415(2) 0.30265(8) 0.0286(3) Uani 1 1 d . . . . .
H4 H 0.211162 0.989156 0.321139 0.034 Uiso 1 1 calc R . . . .
C5 C 0.16507(9) 0.6980(2) 0.35856(7) 0.0240(2) Uani 1 1 d . . . . .
C6 C 0.12400(9) 0.4845(2) 0.32895(8) 0.0246(2) Uani 1 1 d . . . . .
C7 C 0.09916(9) 0.3963(3) 0.45374(8) 0.0304(3) Uani 1 1 d . . . . .
C8 C 0.10574(10) 0.6495(2) 0.47052(8) 0.0311(3) Uani 1 1 d . . . . .
H8A H 0.122633 0.675351 0.531409 0.037 Uiso 1 1 calc R . . . .
H8B H 0.040990 0.719646 0.437869 0.037 Uiso 1 1 calc R . . . .
C9 C 0.18147(9) 0.7706(2) 0.44700(7) 0.0259(3) Uani 1 1 d . . . . .
H9 H 0.169741 0.940026 0.446268 0.031 Uiso 1 1 calc R . . . .
C10 C 0.28414(9) 0.7227(2) 0.51310(8) 0.0262(3) Uani 1 1 d . . . . .
C11 C 0.47672(10) 0.8435(2) 0.59010(8) 0.0285(3) Uani 1 1 d . . . . .
C12 C 0.53866(11) 0.6545(2) 0.60972(9) 0.0345(3) Uani 1 1 d . . . . .
H12 H 0.526382 0.534022 0.569599 0.041 Uiso 1 1 calc R . . . .
C13 C 0.61814(11) 0.6406(3) 0.68730(9) 0.0365(3) Uani 1 1 d . . . . .
H13 H 0.661058 0.512385 0.701091 0.044 Uiso 1 1 calc R . . . .
C14 C 0.63316(10) 0.8178(3) 0.74387(8) 0.0330(3) Uani 1 1 d . . . . .
C15 C 0.57353(10) 1.0074(3) 0.72670(9) 0.0352(3) Uani 1 1 d . . . . .
H15 H 0.586217 1.126592 0.767363 0.042 Uiso 1 1 calc R . . . .
C16 C 0.49448(10) 1.0205(2) 0.64870(9) 0.0323(3) Uani 1 1 d . . . . .
H16 H 0.452391 1.150267 0.635191 0.039 Uiso 1 1 calc R . . . .


_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 C10 1.8077(14) . ?
S1 C11 1.7776(15) . ?
F1 C10 1.3709(16) . ?
F2 C10 1.3660(15) . ?
F3 C14 1.3540(16) . ?
O1 C6 1.3982(15) . ?
O1 C7 1.3679(17) . ?
O2 C7 1.2011(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.3828(19) . ?
C1 C6 1.3840(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3889(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.3917(18) . ?
C5 C6 1.3869(18) . ?
C5 C9 1.5095(17) . ?
C7 C8 1.496(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5323(19) . ?
C9 H9 1.0000 . ?
C9 C10 1.5210(19) . ?
C11 C12 1.389(2) . ?
C11 C16 1.3925(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.375(2) . ?
C14 C15 1.374(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(2) . ?
C16 H16 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
C11 S1 C10 99.40(7) . . ?
C7 O1 C6 120.35(11) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.17(13) . . ?
C6 C1 H1 120.4 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.03(12) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 119.91(12) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.95(13) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C9 123.00(12) . . ?
C6 C5 C4 117.76(11) . . ?
C6 C5 C9 119.11(11) . . ?
C1 C6 O1 115.75(12) . . ?
C1 C6 C5 122.18(12) . . ?
C5 C6 O1 122.05(11) . . ?
O1 C7 C8 116.81(11) . . ?
O2 C7 O1 117.19(14) . . ?
O2 C7 C8 125.95(13) . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C7 C8 C9 113.38(11) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C5 C9 C8 108.41(11) . . ?
C5 C9 H9 108.0 . . ?
C5 C9 C10 113.70(10) . . ?
C8 C9 H9 108.0 . . ?
C10 C9 C8 110.57(11) . . ?
C10 C9 H9 108.0 . . ?
F1 C10 S1 110.59(9) . . ?
F1 C10 C9 110.32(10) . . ?
F2 C10 S1 110.10(9) . . ?
F2 C10 F1 104.52(10) . . ?
F2 C10 C9 108.58(10) . . ?
C9 C10 S1 112.42(9) . . ?
C12 C11 S1 120.69(10) . . ?
C12 C11 C16 119.97(13) . . ?
C16 C11 S1 119.32(11) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.45(13) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 121.0 . . ?
C14 C13 C12 118.05(14) . . ?
C14 C13 H13 121.0 . . ?
F3 C14 C13 118.20(13) . . ?
F3 C14 C15 118.65(12) . . ?
C15 C14 C13 123.15(13) . . ?
C14 C15 H15 120.8 . . ?
C14 C15 C16 118.41(13) . . ?
C16 C15 H15 120.8 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 C11 119.97(13) . . ?
C15 C16 H16 120.0 . . ?

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 C11 C12 C13 178.28(11) . . . . ?
S1 C11 C16 C15 -178.68(10) . . . . ?
F3 C14 C15 C16 -179.72(12) . . . . ?
O1 C7 C8 C9 -39.74(16) . . . . ?
O2 C7 C8 C9 142.73(13) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C1 C6 O1 -177.75(11) . . . . ?
C2 C1 C6 C5 0.90(19) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 C6 -0.44(19) . . . . ?
C3 C4 C5 C9 -176.22(12) . . . . ?
C4 C5 C6 O1 178.13(11) . . . . ?
C4 C5 C6 C1 -0.43(18) . . . . ?
C4 C5 C9 C8 147.91(12) . . . . ?
C4 C5 C9 C10 -88.69(15) . . . . ?
C5 C9 C10 S1 58.89(13) . . . . ?
C5 C9 C10 F1 -65.05(13) . . . . ?
C5 C9 C10 F2 -179.04(10) . . . . ?
C6 O1 C7 O2 -177.81(11) . . . . ?
C6 O1 C7 C8 4.44(16) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C6 C5 C9 C8 -27.82(15) . . . . ?
C6 C5 C9 C10 95.58(14) . . . . ?
C7 O1 C6 C1 -161.63(11) . . . . ?
C7 O1 C6 C5 19.71(17) . . . . ?
C7 C8 C9 C5 49.29(14) . . . . ?
C7 C8 C9 C10 -75.97(14) . . . . ?
C8 C9 C10 S1 -178.89(9) . . . . ?
C8 C9 C10 F1 57.17(13) . . . . ?
C8 C9 C10 F2 -56.82(14) . . . . ?
C9 C5 C6 O1 -5.91(17) . . . . ?
C9 C5 C6 C1 175.52(11) . . . . ?
C10 S1 C11 C12 89.82(12) . . . . ?
C10 S1 C11 C16 -91.92(12) . . . . ?
C11 S1 C10 F1 -72.33(9) . . . . ?
C11 S1 C10 F2 42.67(10) . . . . ?
C11 S1 C10 C9 163.88(9) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C11 C16 C15 -0.4(2) . . . . ?
C12 C13 C14 F3 179.36(12) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C14 C15 C16 C11 0.4(2) . . . . ?
C16 C11 C12 C13 0.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
