# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_20180793-syt-4-117-1_0m
_database_code_depnum_ccdc_archive 'CCDC 1954943'
loop_
_audit_author_name
_audit_author_address
'Yu-Tuo Sun'
;SUSTech
China
;
_audit_update_record             
;
2019-09-20 deposited with the CCDC.	2019-11-28 downloaded from the CCDC.
;
_audit_creation_date             2018-08-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 F3 N O2 S'
_chemical_formula_sum            'C16 H14 F3 N O2 S'
_chemical_formula_weight         341.34
_chemical_absolute_configuration rm
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.6807(9)
_cell_length_b                   10.5121(12)
_cell_length_c                   16.8506(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1537.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5498
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.035
_cell_measurement_theta_min      2.284
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0991 before and 0.0562 after correction. The Ratio of minimum to maximum transmission is 0.8895. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13737
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         2.284
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3296
_reflns_number_total             3519
_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         0.215
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 1314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3519
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.050
_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)+(0.0552P)²+0.1651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0923
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.86 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3), C11(H11), C15(H15), C12(H12), C14(H14)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.08535(7) 0.73853(5) 0.07717(3) 0.02662(16) Uani 1 1 d . . . . .
F2 F -0.34150(17) 0.90991(18) 0.15249(10) 0.0420(4) Uani 1 1 d . . . . .
F1 F -0.2045(2) 0.81890(17) 0.24248(10) 0.0441(4) Uani 1 1 d . . . . .
F3 F -0.2234(2) 1.02238(17) 0.23980(10) 0.0445(4) Uani 1 1 d . . . . .
O1 O 0.1580(2) 0.77270(19) 0.00322(10) 0.0404(5) Uani 1 1 d . . . . .
O2 O 0.0689(3) 0.60431(16) 0.09038(11) 0.0410(5) Uani 1 1 d . . . . .
N1 N -0.0778(3) 0.81016(19) 0.09085(12) 0.0293(4) Uani 1 1 d D . . . .
C10 C -0.0801(3) 1.0496(2) 0.08750(13) 0.0248(4) Uani 1 1 d . . . . .
C8 C -0.0716(3) 0.9279(2) 0.13793(12) 0.0230(4) Uani 1 1 d . . . . .
C9 C -0.2114(3) 0.9199(2) 0.19376(14) 0.0301(5) Uani 1 1 d . . . . .
C5 C 0.1279(3) 0.9820(2) 0.25095(14) 0.0298(5) Uani 1 1 d . . . . .
H5 H 0.0651 1.0477 0.2722 0.036 Uiso 1 1 calc R . . . .
C1 C 0.1721(3) 0.8173(2) 0.15624(13) 0.0254(5) Uani 1 1 d . . . . .
C6 C 0.0790(3) 0.9141(2) 0.18483(12) 0.0242(4) Uani 1 1 d . . . . .
C4 C 0.2694(3) 0.9536(3) 0.28613(15) 0.0338(6) Uani 1 1 d . . . . .
C2 C 0.3140(3) 0.7875(2) 0.18908(15) 0.0335(5) Uani 1 1 d . . . . .
H2 H 0.3769 0.7222 0.1674 0.040 Uiso 1 1 calc R . . . .
C3 C 0.3604(3) 0.8567(3) 0.25444(17) 0.0378(6) Uani 1 1 d . . . . .
H3 H 0.4567 0.8378 0.2785 0.045 Uiso 1 1 calc R . . . .
C11 C -0.1386(4) 1.0446(3) 0.01089(15) 0.0378(6) Uani 1 1 d . . . . .
H11 H -0.1735 0.9658 -0.0101 0.045 Uiso 1 1 calc R . . . .
C13 C -0.0985(4) 1.2704(3) -0.00727(17) 0.0397(6) Uani 1 1 d . . . . .
C15 C -0.0335(4) 1.1667(3) 0.11649(17) 0.0410(7) Uani 1 1 d . . . . .
H15 H 0.0053 1.1729 0.1691 0.049 Uiso 1 1 calc R . . . .
C12 C -0.1466(4) 1.1538(3) -0.03527(16) 0.0449(7) Uani 1 1 d . . . . .
H12 H -0.1864 1.1480 -0.0877 0.054 Uiso 1 1 calc R . . . .
C14 C -0.0425(4) 1.2755(3) 0.06971(18) 0.0460(7) Uani 1 1 d . . . . .
H14 H -0.0098 1.3547 0.0909 0.055 Uiso 1 1 calc R . . . .
C7 C 0.3199(4) 1.0272(3) 0.35866(19) 0.0521(8) Uani 1 1 d . . . . .
H7A H 0.3493 1.1137 0.3431 0.078 Uiso 1 1 calc GR . . . .
H7B H 0.4084 0.9845 0.3831 0.078 Uiso 1 1 calc GR . . . .
H7C H 0.2349 1.0311 0.3968 0.078 Uiso 1 1 calc GR . . . .
C16 C -0.1041(5) 1.3892(3) -0.0587(2) 0.0634(10) Uani 1 1 d . . . . .
H16A H -0.0703 1.3681 -0.1126 0.095 Uiso 1 1 calc GR . . . .
H16B H -0.0358 1.4541 -0.0363 0.095 Uiso 1 1 calc GR . . . .
H16C H -0.2098 1.4218 -0.0603 0.095 Uiso 1 1 calc GR . . . .
H1 H -0.149(3) 0.792(3) 0.0567(16) 0.045(9) Uiso 1 1 d 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 O1 1.4419(18) . ?
S1 O2 1.4354(18) . ?
S1 N1 1.621(2) . ?
S1 C1 1.740(2) . ?
F2 C9 1.330(3) . ?
F1 C9 1.344(3) . ?
F3 C9 1.331(3) . ?
N1 C8 1.471(3) . ?
N1 H1 0.86(2) . ?
C10 C8 1.538(3) . ?
C10 C11 1.388(3) . ?
C10 C15 1.385(3) . ?
C8 C9 1.538(3) . ?
C8 C6 1.534(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C5 C4 1.396(4) . ?
C1 C6 1.386(3) . ?
C1 C2 1.387(4) . ?
C4 C3 1.396(4) . ?
C4 C7 1.512(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(4) . ?
C3 H3 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.389(4) . ?
C13 C12 1.378(4) . ?
C13 C14 1.386(4) . ?
C13 C16 1.520(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.391(4) . ?
C12 H12 0.9500 . ?
C14 H14 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 N1 112.91(12) . . ?
O1 S1 C1 110.73(12) . . ?
O2 S1 O1 114.98(12) . . ?
O2 S1 N1 110.36(12) . . ?
O2 S1 C1 113.06(12) . . ?
N1 S1 C1 92.77(11) . . ?
S1 N1 H1 115(2) . . ?
C8 N1 S1 115.80(17) . . ?
C8 N1 H1 125(2) . . ?
C11 C10 C8 120.0(2) . . ?
C15 C10 C8 122.0(2) . . ?
C15 C10 C11 117.9(2) . . ?
N1 C8 C10 113.58(17) . . ?
N1 C8 C9 104.78(19) . . ?
N1 C8 C6 103.29(18) . . ?
C10 C8 C9 110.18(19) . . ?
C6 C8 C10 113.85(19) . . ?
C6 C8 C9 110.63(18) . . ?
F2 C9 F1 107.1(2) . . ?
F2 C9 F3 107.6(2) . . ?
F2 C9 C8 110.76(19) . . ?
F1 C9 C8 112.4(2) . . ?
F3 C9 F1 106.7(2) . . ?
F3 C9 C8 112.0(2) . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C1 S1 111.30(18) . . ?
C6 C1 C2 123.0(2) . . ?
C2 C1 S1 125.66(19) . . ?
C5 C6 C8 128.7(2) . . ?
C1 C6 C8 112.77(19) . . ?
C1 C6 C5 118.5(2) . . ?
C5 C4 C7 119.3(3) . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 C7 121.2(3) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.3(2) . . ?
C3 C2 H2 121.3 . . ?
C4 C3 H3 119.2 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.2 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C12 C13 C14 117.4(2) . . ?
C12 C13 C16 121.7(3) . . ?
C14 C13 C16 120.9(3) . . ?
C10 C15 H15 119.5 . . ?
C10 C15 C14 120.9(3) . . ?
C14 C15 H15 119.5 . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.9(3) . . ?
C13 C12 H12 119.1 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
S1 N1 C8 C10 102.3(2) . . . . ?
S1 N1 C8 C9 -137.39(17) . . . . ?
S1 N1 C8 C6 -21.5(2) . . . . ?
S1 C1 C6 C8 -1.7(2) . . . . ?
S1 C1 C6 C5 176.54(18) . . . . ?
S1 C1 C2 C3 -176.6(2) . . . . ?
O1 S1 N1 C8 -94.91(18) . . . . ?
O1 S1 C1 C6 106.25(18) . . . . ?
O1 S1 C1 C2 -75.2(2) . . . . ?
O2 S1 N1 C8 134.86(17) . . . . ?
O2 S1 C1 C6 -123.06(18) . . . . ?
O2 S1 C1 C2 55.5(2) . . . . ?
N1 S1 C1 C6 -9.54(19) . . . . ?
N1 S1 C1 C2 169.0(2) . . . . ?
N1 C8 C9 F2 -58.6(2) . . . . ?
N1 C8 C9 F1 61.2(2) . . . . ?
N1 C8 C9 F3 -178.76(19) . . . . ?
N1 C8 C6 C5 -164.5(2) . . . . ?
N1 C8 C6 C1 13.5(2) . . . . ?
C10 C8 C9 F2 63.9(2) . . . . ?
C10 C8 C9 F1 -176.29(19) . . . . ?
C10 C8 C9 F3 -56.2(3) . . . . ?
C10 C8 C6 C5 71.9(3) . . . . ?
C10 C8 C6 C1 -110.1(2) . . . . ?
C10 C11 C12 C13 -0.4(5) . . . . ?
C10 C15 C14 C13 0.0(5) . . . . ?
C8 C10 C11 C12 -179.9(3) . . . . ?
C8 C10 C15 C14 -179.9(3) . . . . ?
C9 C8 C6 C5 -52.8(3) . . . . ?
C9 C8 C6 C1 125.1(2) . . . . ?
C5 C4 C3 C2 -0.1(4) . . . . ?
C1 S1 N1 C8 19.00(18) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C6 C8 C9 F2 -169.3(2) . . . . ?
C6 C8 C9 F1 -49.5(3) . . . . ?
C6 C8 C9 F3 70.5(3) . . . . ?
C6 C5 C4 C3 -0.2(4) . . . . ?
C6 C5 C4 C7 -179.2(3) . . . . ?
C6 C1 C2 C3 1.7(4) . . . . ?
C4 C5 C6 C8 179.1(2) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C2 C1 C6 C8 179.8(2) . . . . ?
C2 C1 C6 C5 -2.0(4) . . . . ?
C11 C10 C8 N1 19.8(3) . . . . ?
C11 C10 C8 C9 -97.4(3) . . . . ?
C11 C10 C8 C6 137.6(2) . . . . ?
C11 C10 C15 C14 -1.1(4) . . . . ?
C15 C10 C8 N1 -161.5(3) . . . . ?
C15 C10 C8 C9 81.3(3) . . . . ?
C15 C10 C8 C6 -43.6(3) . . . . ?
C15 C10 C11 C12 1.3(4) . . . . ?
C12 C13 C14 C15 0.8(5) . . . . ?
C14 C13 C12 C11 -0.6(5) . . . . ?
C7 C4 C3 C2 178.9(3) . . . . ?
C16 C13 C12 C11 178.6(3) . . . . ?
C16 C13 C14 C15 -178.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
