# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2075197'
loop_
_audit_author_name
_audit_author_address
'Gangguo Zhu'
;Zhejiang Normal University
China
;
_audit_update_record             
;
2021-04-03 deposited with the CCDC.	2021-06-13 downloaded from the CCDC.
;
_audit_creation_date             2021-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H14 F3 N O2 S'
_chemical_formula_sum            'C18 H14 F3 N O2 S'
_chemical_formula_weight         365.36
_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'
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'

_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                   10.8837(3)
_cell_length_b                   16.9833(5)
_cell_length_c                   9.3334(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.008(2)
_cell_angle_gamma                90
_cell_volume                     1680.93(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.110
_cell_measurement_theta_min      2.264
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            55354
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.434
_diffrn_reflns_theta_min         2.264
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3048
_reflns_number_total             3818
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.359
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0144(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3818
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+1.1734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1287
_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:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_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 0.88599(5) 0.03453(3) 0.23773(6) 0.04770(18) Uani 1 1 d . . . . .
C1 C 0.86805(19) 0.12004(12) 0.3360(2) 0.0417(4) Uani 1 1 d . . . . .
C2 C 0.7449(2) 0.13975(16) 0.3403(3) 0.0562(6) Uani 1 1 d . . . . .
H2 H 0.6785 0.1066 0.2983 0.067 Uiso 1 1 calc R . . . .
C3 C 0.7220(2) 0.20901(18) 0.4074(3) 0.0679(7) Uani 1 1 d . . . . .
H3 H 0.6400 0.2231 0.4100 0.082 Uiso 1 1 calc R . . . .
C4 C 0.8213(3) 0.25706(16) 0.4705(3) 0.0658(7) Uani 1 1 d . . . . .
H4 H 0.8058 0.3036 0.5159 0.079 Uiso 1 1 calc R . . . .
C5 C 0.9440(2) 0.23711(13) 0.4673(3) 0.0527(5) Uani 1 1 d . . . . .
H5 H 1.0095 0.2704 0.5112 0.063 Uiso 1 1 calc R . . . .
C6 C 0.97154(19) 0.16781(12) 0.3994(2) 0.0398(4) Uani 1 1 d . . . . .
C7 C 1.10152(18) 0.14330(11) 0.4009(2) 0.0373(4) Uani 1 1 d . . . . .
C8 C 1.21124(18) 0.19715(11) 0.4452(2) 0.0386(4) Uani 1 1 d . . . . .
C9 C 1.2142(2) 0.27186(13) 0.3849(2) 0.0499(5) Uani 1 1 d . . . . .
H9 H 1.1447 0.2900 0.3157 0.060 Uiso 1 1 calc R . . . .
C10 C 1.3193(2) 0.31941(14) 0.4268(3) 0.0573(6) Uani 1 1 d . . . . .
H10 H 1.3194 0.3694 0.3862 0.069 Uiso 1 1 calc R . . . .
C11 C 1.4234(2) 0.29347(14) 0.5275(3) 0.0570(6) Uani 1 1 d . . . . .
H11 H 1.4943 0.3254 0.5546 0.068 Uiso 1 1 calc R . . . .
C12 C 1.4220(2) 0.22000(15) 0.5879(3) 0.0576(6) Uani 1 1 d . . . . .
H12 H 1.4923 0.2021 0.6561 0.069 Uiso 1 1 calc R . . . .
C13 C 1.3168(2) 0.17224(13) 0.5482(2) 0.0473(5) Uani 1 1 d . . . . .
H13 H 1.3169 0.1228 0.5911 0.057 Uiso 1 1 calc R . . . .
C14 C 1.11918(18) 0.06805(11) 0.36840(19) 0.0365(4) Uani 1 1 d . . . . .
C15 C 1.22187(19) 0.01303(12) 0.3441(2) 0.0408(4) Uani 1 1 d . . . . .
H15 H 1.2757 -0.0050 0.4370 0.049 Uiso 1 1 calc R . . . .
C16 C 1.2986(2) 0.04221(13) 0.2372(3) 0.0503(5) Uani 1 1 d . . . . .
H16A H 1.2428 0.0499 0.1414 0.060 Uiso 1 1 calc R . . . .
H16B H 1.3357 0.0928 0.2708 0.060 Uiso 1 1 calc R . . . .
C17 C 1.4003(3) -0.01318(17) 0.2226(3) 0.0620(6) Uani 1 1 d . . . . .
C18 C 1.1147(2) -0.04642(12) 0.2823(2) 0.0471(5) Uani 1 1 d . . . . .
H18A H 1.0982 -0.0532 0.1765 0.056 Uiso 1 1 calc R . . . .
H18B H 1.1240 -0.0968 0.3325 0.056 Uiso 1 1 calc R . . . .
N1 N 1.02554(16) 0.00883(10) 0.33229(17) 0.0408(4) Uani 1 1 d . . . . .
O1 O 0.8911(2) 0.05464(12) 0.09095(17) 0.0739(6) Uani 1 1 d . . . . .
O2 O 0.79681(18) -0.02379(11) 0.2566(3) 0.0800(6) Uani 1 1 d . . . . .
F1 F 1.35673(18) -0.08510(11) 0.1846(2) 0.0963(6) Uani 1 1 d . . . . .
F2 F 1.48559(17) -0.02267(14) 0.3458(2) 0.1080(7) Uani 1 1 d . . . . .
F3 F 1.4633(2) 0.01038(15) 0.1245(3) 0.1224(9) Uani 1 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
S1 C1 1.752(2) . ?
S1 N1 1.6349(18) . ?
S1 O1 1.4251(18) . ?
S1 O2 1.4253(19) . ?
C1 C2 1.391(3) . ?
C1 C6 1.406(3) . ?
C2 C3 1.381(4) . ?
C3 C4 1.377(4) . ?
C4 C5 1.384(3) . ?
C5 C6 1.401(3) . ?
C6 C7 1.472(3) . ?
C7 C8 1.487(3) . ?
C7 C14 1.337(3) . ?
C8 C9 1.391(3) . ?
C8 C13 1.388(3) . ?
C9 C10 1.383(3) . ?
C10 C11 1.373(3) . ?
C11 C12 1.370(4) . ?
C12 C13 1.384(3) . ?
C14 C15 1.512(3) . ?
C14 N1 1.417(2) . ?
C15 C16 1.521(3) . ?
C15 C18 1.552(3) . ?
C16 C17 1.482(3) . ?
C17 F1 1.329(3) . ?
C17 F2 1.315(3) . ?
C17 F3 1.323(3) . ?
C18 N1 1.497(3) . ?

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
N1 S1 C1 97.95(9) . . ?
O1 S1 C1 109.72(11) . . ?
O1 S1 N1 110.52(11) . . ?
O2 S1 C1 110.62(12) . . ?
O2 S1 N1 108.87(11) . . ?
O2 S1 O1 117.42(13) . . ?
C2 C1 S1 115.87(17) . . ?
C2 C1 C6 122.3(2) . . ?
C6 C1 S1 121.71(15) . . ?
C3 C2 C1 119.4(2) . . ?
C4 C3 C2 119.6(2) . . ?
C3 C4 C5 120.9(2) . . ?
C4 C5 C6 121.4(2) . . ?
C1 C6 C7 121.20(17) . . ?
C5 C6 C1 116.25(19) . . ?
C5 C6 C7 122.46(19) . . ?
C6 C7 C8 122.59(17) . . ?
C14 C7 C6 117.07(18) . . ?
C14 C7 C8 120.23(17) . . ?
C9 C8 C7 122.58(18) . . ?
C13 C8 C7 119.55(18) . . ?
C13 C8 C9 117.86(19) . . ?
C10 C9 C8 120.8(2) . . ?
C11 C10 C9 120.6(2) . . ?
C12 C11 C10 119.3(2) . . ?
C11 C12 C13 120.6(2) . . ?
C12 C13 C8 120.9(2) . . ?
C7 C14 C15 140.63(19) . . ?
C7 C14 N1 126.84(18) . . ?
N1 C14 C15 92.41(15) . . ?
C14 C15 C16 115.50(16) . . ?
C14 C15 C18 86.47(15) . . ?
C16 C15 C18 116.50(17) . . ?
C17 C16 C15 112.66(19) . . ?
F1 C17 C16 112.3(2) . . ?
F2 C17 C16 113.1(2) . . ?
F2 C17 F1 105.1(2) . . ?
F2 C17 F3 105.6(2) . . ?
F3 C17 C16 112.7(2) . . ?
F3 C17 F1 107.6(2) . . ?
N1 C18 C15 87.84(14) . . ?
C14 N1 S1 118.02(13) . . ?
C14 N1 C18 92.12(15) . . ?
C18 N1 S1 125.98(13) . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
