# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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 2416854'
loop_
_audit_author_name
_audit_author_address
'xie xiaofei'
;Nanjing Agricultural University
China
;
_audit_update_record             
;
2025-01-14 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 Br N O S'
_chemical_formula_weight         362.28

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'
Br Br -0.2901 2.4595 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.8254(11)
_cell_length_b                   7.5174(14)
_cell_length_c                   18.148(4)
_cell_angle_alpha                87.425(3)
_cell_angle_beta                 84.849(3)
_cell_angle_gamma                84.586(4)
_cell_volume                     787.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1813
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      26.88

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    2.740
_shelx_estimated_absorpt_T_min   0.536
_shelx_estimated_absorpt_T_max   0.559
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4028
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.724
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             2758
_reflns_number_gt                2224
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0486P)²+0.4847P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2758
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_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
Br1 Br 1.04765(8) 0.77322(6) 0.05450(2) 0.06588(19) Uani 1 1 d . . . . .
S1 S 0.90587(13) 0.89997(11) 0.70852(4) 0.0353(2) Uani 1 1 d . . . . .
O1 O 0.7671(4) 0.4566(3) 0.40326(13) 0.0461(6) Uani 1 1 d . . . . .
H1 H 0.6936 0.3903 0.3817 0.069 Uiso 1 1 calc R U . . .
N1 N 0.5454(4) 0.7534(3) 0.67539(13) 0.0297(5) Uani 1 1 d . . . . .
C5 C 0.5399(5) 0.7475(4) 0.75231(15) 0.0277(6) Uani 1 1 d . . . . .
C12 C 0.7906(5) 0.6779(4) 0.30263(15) 0.0282(6) Uani 1 1 d . . . . .
C6 C 0.7246(5) 0.8212(4) 0.78094(16) 0.0304(6) Uani 1 1 d . . . . .
C13 C 1.0143(5) 0.6170(4) 0.27589(16) 0.0318(7) Uani 1 1 d . . . . .
H13 H 1.1124 0.5547 0.3078 0.038 Uiso 1 1 calc R U . . .
C7 C 0.7258(5) 0.8277(4) 0.64577(16) 0.0309(7) Uani 1 1 d . . . . .
C15 C 0.9462(6) 0.7419(4) 0.15602(16) 0.0366(7) Uani 1 1 d . . . . .
C4 C 0.3733(5) 0.6733(4) 0.80094(16) 0.0336(7) Uani 1 1 d . . . . .
H4 H 0.2495 0.6243 0.7830 0.040 Uiso 1 1 calc R U . . .
C17 C 0.6501(5) 0.7759(4) 0.25482(17) 0.0370(7) Uani 1 1 d . . . . .
H17 H 0.5024 0.8214 0.2725 0.044 Uiso 1 1 calc R U . . .
C14 C 1.0928(5) 0.6476(4) 0.20275(17) 0.0350(7) Uani 1 1 d . . . . .
H14 H 1.2421 0.6054 0.1852 0.042 Uiso 1 1 calc R U . . .
C11 C 0.7030(5) 0.6375(4) 0.38176(16) 0.0338(7) Uani 1 1 d . . . . .
H11 H 0.5337 0.6575 0.3862 0.041 Uiso 1 1 calc R U . . .
C16 C 0.7253(6) 0.8072(4) 0.18155(18) 0.0418(8) Uani 1 1 d . . . . .
H16 H 0.6286 0.8714 0.1498 0.050 Uiso 1 1 calc R U . . .
C3 C 0.3938(6) 0.6733(5) 0.87600(17) 0.0412(8) Uani 1 1 d . . . . .
H3 H 0.2824 0.6242 0.9086 0.049 Uiso 1 1 calc R U . . .
C9 C 0.7054(6) 0.7274(4) 0.51536(16) 0.0387(8) Uani 1 1 d . . . . .
H9A H 0.5375 0.7398 0.5189 0.046 Uiso 1 1 calc R U . . .
H9B H 0.7553 0.6066 0.5319 0.046 Uiso 1 1 calc R U . . .
C1 C 0.7460(6) 0.8201(4) 0.85660(17) 0.0388(7) Uani 1 1 d . . . . .
H1A H 0.8697 0.8683 0.8750 0.047 Uiso 1 1 calc R U . . .
C10 C 0.7972(6) 0.7573(4) 0.43529(16) 0.0366(7) Uani 1 1 d . . . . .
H10A H 0.9646 0.7364 0.4316 0.044 Uiso 1 1 calc R U . . .
H10B H 0.7579 0.8812 0.4204 0.044 Uiso 1 1 calc R U . . .
C8 C 0.7890(6) 0.8586(4) 0.56534(17) 0.0392(7) Uani 1 1 d . . . . .
H8A H 0.9563 0.8544 0.5572 0.047 Uiso 1 1 calc R U . . .
H8B H 0.7268 0.9781 0.5510 0.047 Uiso 1 1 calc R U . . .
C2 C 0.5789(6) 0.7456(5) 0.90385(18) 0.0455(8) Uani 1 1 d . . . . .
H2 H 0.5898 0.7437 0.9547 0.055 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
Br1 C15 1.895(3) . ?
S1 C6 1.730(3) . ?
S1 C7 1.752(3) . ?
O1 C11 1.422(4) . ?
O1 H1 0.8200 . ?
N1 C7 1.299(4) . ?
N1 C5 1.392(4) . ?
C5 C4 1.392(4) . ?
C5 C6 1.405(4) . ?
C12 C17 1.386(4) . ?
C12 C13 1.392(4) . ?
C12 C11 1.508(4) . ?
C6 C1 1.390(4) . ?
C13 C14 1.381(4) . ?
C13 H13 0.9300 . ?
C7 C8 1.486(4) . ?
C15 C16 1.380(5) . ?
C15 C14 1.383(4) . ?
C4 C3 1.378(4) . ?
C4 H4 0.9300 . ?
C17 C16 1.379(4) . ?
C17 H17 0.9300 . ?
C14 H14 0.9300 . ?
C11 C10 1.525(4) . ?
C11 H11 0.9800 . ?
C16 H16 0.9300 . ?
C3 C2 1.395(5) . ?
C3 H3 0.9300 . ?
C9 C8 1.511(4) . ?
C9 C10 1.517(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C1 C2 1.381(5) . ?
C1 H1A 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C2 H2 0.9300 . ?

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
C6 S1 C7 89.48(14) . . ?
C11 O1 H1 109.5 . . ?
C7 N1 C5 110.9(2) . . ?
C4 C5 N1 125.8(3) . . ?
C4 C5 C6 119.2(3) . . ?
N1 C5 C6 115.0(2) . . ?
C17 C12 C13 118.5(3) . . ?
C17 C12 C11 120.8(3) . . ?
C13 C12 C11 120.7(3) . . ?
C1 C6 C5 121.6(3) . . ?
C1 C6 S1 129.2(2) . . ?
C5 C6 S1 109.2(2) . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
N1 C7 C8 126.4(3) . . ?
N1 C7 S1 115.4(2) . . ?
C8 C7 S1 118.2(2) . . ?
C16 C15 C14 121.1(3) . . ?
C16 C15 Br1 119.8(2) . . ?
C14 C15 Br1 119.1(2) . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C16 C17 C12 121.2(3) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
O1 C11 C12 111.2(2) . . ?
O1 C11 C10 108.0(3) . . ?
C12 C11 C10 111.8(2) . . ?
O1 C11 H11 108.6 . . ?
C12 C11 H11 108.6 . . ?
C10 C11 H11 108.6 . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C8 C9 C10 111.8(2) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C2 C1 C6 118.3(3) . . ?
C2 C1 H1A 120.8 . . ?
C6 C1 H1A 120.8 . . ?
C9 C10 C11 113.8(2) . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C7 C8 C9 115.3(3) . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8B 108.4 . . ?
C9 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?

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
C7 N1 C5 C4 -178.5(3) . . . . ?
C7 N1 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
N1 C5 C6 C1 -178.1(3) . . . . ?
C4 C5 C6 S1 179.1(2) . . . . ?
N1 C5 C6 S1 0.4(3) . . . . ?
C7 S1 C6 C1 177.8(3) . . . . ?
C7 S1 C6 C5 -0.6(2) . . . . ?
C17 C12 C13 C14 -2.3(4) . . . . ?
C11 C12 C13 C14 177.5(3) . . . . ?
C5 N1 C7 C8 -179.5(3) . . . . ?
C5 N1 C7 S1 -0.5(3) . . . . ?
C6 S1 C7 N1 0.7(2) . . . . ?
C6 S1 C7 C8 179.7(2) . . . . ?
N1 C5 C4 C3 178.3(3) . . . . ?
C6 C5 C4 C3 -0.2(4) . . . . ?
C13 C12 C17 C16 2.5(5) . . . . ?
C11 C12 C17 C16 -177.3(3) . . . . ?
C16 C15 C14 C13 0.8(5) . . . . ?
Br1 C15 C14 C13 -176.7(2) . . . . ?
C12 C13 C14 C15 0.6(5) . . . . ?
C17 C12 C11 O1 136.3(3) . . . . ?
C13 C12 C11 O1 -43.4(4) . . . . ?
C17 C12 C11 C10 -102.8(3) . . . . ?
C13 C12 C11 C10 77.4(4) . . . . ?
C12 C17 C16 C15 -1.1(5) . . . . ?
C14 C15 C16 C17 -0.6(5) . . . . ?
Br1 C15 C16 C17 176.9(2) . . . . ?
C5 C4 C3 C2 -0.2(5) . . . . ?
C5 C6 C1 C2 -0.6(5) . . . . ?
S1 C6 C1 C2 -178.7(3) . . . . ?
C8 C9 C10 C11 -175.6(3) . . . . ?
O1 C11 C10 C9 -60.0(3) . . . . ?
C12 C11 C10 C9 177.4(3) . . . . ?
N1 C7 C8 C9 -28.3(5) . . . . ?
S1 C7 C8 C9 152.8(2) . . . . ?
C10 C9 C8 C7 -174.4(3) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C4 C3 C2 C1 0.3(5) . . . . ?

_refine_diff_density_max         0.635
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.064



####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2416902'
loop_
_audit_author_name
_audit_author_address
'xie xiaofei'
;Nanjing Agricultural University
China
;
_audit_update_record             
;
2025-01-14 deposited with the CCDC.	2025-05-13 downloaded from the CCDC.
;
_audit_creation_date             2024-08-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 F3 N2 O2 S'
_chemical_formula_sum            'C20 H19 F3 N2 O2 S'
_chemical_formula_weight         408.43
_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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   16.4672(4)
_cell_length_b                   13.2488(3)
_cell_length_c                   9.8017(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.0310(10)
_cell_angle_gamma                90
_cell_volume                     2044.66(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4514
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      66.427
_cell_measurement_theta_min      2.807
_shelx_estimated_absorpt_T_max   0.799
_shelx_estimated_absorpt_T_min   0.682
_exptl_absorpt_coefficient_mu    1.805
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5675
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1285 before and 0.0575 after correction.
The Ratio of minimum to maximum transmission is 0.7536.
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    1.327
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19513
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.475
_diffrn_reflns_theta_min         2.806
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2578
_reflns_number_total             3748
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.794
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3748
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0678
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1484P)²+0.2969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2145
_refine_ls_wR_factor_ref         0.2415
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C15(H15), C1(H1), C3(H3), C16(H16), C2(H2A), C4(H4), C19(H19), C18(H18)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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 0.62040(5) 0.30790(7) 0.38092(10) 0.0860(4) Uani 1 1 d . . . . .
O1 O 0.20007(15) 0.19803(18) 0.7287(2) 0.0886(7) Uani 1 1 d . . . . .
N1 N 0.52394(16) 0.1705(2) 0.4412(3) 0.0737(7) Uani 1 1 d . . . . .
N2 N 0.23376(16) 0.2712(2) 0.5457(2) 0.0742(7) Uani 1 1 d . . . . .
H2 H 0.228947 0.269372 0.455985 0.089 Uiso 1 1 calc R . . . .
O2 O 0.1115(2) 0.6935(2) 0.7356(4) 0.1210(10) Uani 1 1 d . . . . .
C6 C 0.58241(18) 0.1203(2) 0.3861(3) 0.0717(7) Uani 1 1 d . . . . .
C7 C 0.53716(18) 0.2672(3) 0.4449(3) 0.0745(8) Uani 1 1 d . . . . .
C11 C 0.28813(19) 0.3472(3) 0.6346(3) 0.0741(8) Uani 1 1 d . . . . .
H11 H 0.316321 0.315926 0.726922 0.089 Uiso 1 1 calc R . . . .
C12 C 0.19116(19) 0.2043(2) 0.6002(3) 0.0732(8) Uani 1 1 d . . . . .
C14 C 0.23846(18) 0.4367(2) 0.6620(3) 0.0712(7) Uani 1 1 d . . . . .
C5 C 0.63959(19) 0.1841(2) 0.3475(3) 0.0759(8) Uani 1 1 d . . . . .
C15 C 0.2686(2) 0.4924(3) 0.7838(3) 0.0861(9) Uani 1 1 d . . . . .
H15 H 0.318538 0.472355 0.851304 0.103 Uiso 1 1 calc R . . . .
C9 C 0.4141(2) 0.2992(2) 0.5445(3) 0.0788(8) Uani 1 1 d . . . . .
H9A H 0.381320 0.252930 0.472650 0.095 Uiso 1 1 calc R . . . .
H9B H 0.437542 0.261579 0.632108 0.095 Uiso 1 1 calc R . . . .
C8 C 0.48628(19) 0.3436(3) 0.4953(3) 0.0776(8) Uani 1 1 d . . . . .
H8A H 0.462542 0.390968 0.418470 0.093 Uiso 1 1 calc R . . . .
H8B H 0.523817 0.381007 0.573712 0.093 Uiso 1 1 calc R . . . .
F2 F 0.0238(2) 0.7749(3) 0.8185(4) 0.1825(15) Uani 1 1 d . . . . .
C1 C 0.5866(2) 0.0170(3) 0.3701(3) 0.0806(8) Uani 1 1 d . . . . .
H1 H 0.548182 -0.025402 0.394818 0.097 Uiso 1 1 calc R . . . .
C10 C 0.3572(2) 0.3812(3) 0.5693(3) 0.0787(8) Uani 1 1 d . . . . .
H10A H 0.330072 0.413814 0.478800 0.094 Uiso 1 1 calc R . . . .
H10B H 0.392068 0.431453 0.631677 0.094 Uiso 1 1 calc R . . . .
C3 C 0.7060(2) 0.0412(3) 0.2773(4) 0.0950(11) Uani 1 1 d . . . . .
H3 H 0.746830 0.013157 0.240221 0.114 Uiso 1 1 calc R . . . .
C16 C 0.2271(2) 0.5776(3) 0.8093(4) 0.0905(10) Uani 1 1 d . . . . .
H16 H 0.249383 0.615188 0.891953 0.109 Uiso 1 1 calc R . . . .
C2 C 0.6484(2) -0.0220(3) 0.3171(4) 0.0895(10) Uani 1 1 d . . . . .
H2A H 0.652201 -0.091485 0.307363 0.107 Uiso 1 1 calc R . . . .
C4 C 0.7029(2) 0.1436(3) 0.2926(4) 0.0881(10) Uani 1 1 d . . . . .
H4 H 0.741461 0.185484 0.267458 0.106 Uiso 1 1 calc R . . . .
C13 C 0.1324(2) 0.1355(3) 0.4954(4) 0.0949(10) Uani 1 1 d . . . . .
H13A H 0.155772 0.068571 0.505255 0.142 Uiso 1 1 calc GR . . . .
H13B H 0.125548 0.159472 0.400237 0.142 Uiso 1 1 calc GR . . . .
H13C H 0.078151 0.134276 0.513384 0.142 Uiso 1 1 calc GR . . . .
C17 C 0.1537(2) 0.6056(3) 0.7131(4) 0.0895(9) Uani 1 1 d . . . . .
F1 F 0.0909(3) 0.6573(4) 0.9367(5) 0.235(2) Uani 1 1 d . . . . .
C19 C 0.1644(3) 0.4690(3) 0.5639(4) 0.1064(13) Uani 1 1 d . . . . .
H19 H 0.143000 0.433212 0.479287 0.128 Uiso 1 1 calc R . . . .
C18 C 0.1218(3) 0.5526(3) 0.5887(4) 0.1122(14) Uani 1 1 d . . . . .
H18 H 0.071784 0.573127 0.521867 0.135 Uiso 1 1 calc R . . . .
C20 C 0.0597(4) 0.6875(6) 0.8119(9) 0.155(3) Uani 1 1 d . . . . .
F3 F -0.0025(3) 0.6256(5) 0.7465(8) 0.289(4) 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 C7 1.751(3) . ?
S1 C5 1.721(3) . ?
O1 C12 1.227(4) . ?
N1 C6 1.402(4) . ?
N1 C7 1.299(4) . ?
N2 H2 0.8600 . ?
N2 C11 1.455(4) . ?
N2 C12 1.335(4) . ?
O2 C17 1.406(4) . ?
O2 C20 1.291(8) . ?
C6 C5 1.397(4) . ?
C6 C1 1.381(5) . ?
C7 C8 1.487(5) . ?
C11 H11 0.9800 . ?
C11 C14 1.509(4) . ?
C11 C10 1.526(4) . ?
C12 C13 1.497(5) . ?
C14 C15 1.367(4) . ?
C14 C19 1.382(5) . ?
C5 C4 1.411(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.525(4) . ?
C9 C10 1.501(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
F2 C20 1.311(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C2 1.404(5) . ?
C3 C4 1.367(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.350(5) . ?
C2 H2A 0.9300 . ?
C4 H4 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C17 C18 1.371(5) . ?
F1 C20 1.245(7) . ?
C19 H19 0.9300 . ?
C19 C18 1.371(5) . ?
C18 H18 0.9300 . ?
C20 F3 1.322(8) . ?

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
C5 S1 C7 88.93(16) . . ?
C7 N1 C6 110.5(3) . . ?
C11 N2 H2 119.2 . . ?
C12 N2 H2 119.2 . . ?
C12 N2 C11 121.6(2) . . ?
C20 O2 C17 118.7(4) . . ?
C5 C6 N1 114.2(3) . . ?
C1 C6 N1 125.2(3) . . ?
C1 C6 C5 120.5(3) . . ?
N1 C7 S1 115.9(2) . . ?
N1 C7 C8 125.1(3) . . ?
C8 C7 S1 119.1(3) . . ?
N2 C11 H11 107.6 . . ?
N2 C11 C14 112.3(2) . . ?
N2 C11 C10 110.9(2) . . ?
C14 C11 H11 107.6 . . ?
C14 C11 C10 110.6(3) . . ?
C10 C11 H11 107.6 . . ?
O1 C12 N2 122.4(3) . . ?
O1 C12 C13 121.5(3) . . ?
N2 C12 C13 116.1(3) . . ?
C15 C14 C11 120.2(3) . . ?
C15 C14 C19 117.5(3) . . ?
C19 C14 C11 122.2(3) . . ?
C6 C5 S1 110.4(2) . . ?
C6 C5 C4 120.3(3) . . ?
C4 C5 S1 129.2(3) . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.8(3) . . ?
C16 C15 H15 119.1 . . ?
H9A C9 H9B 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C10 C9 C8 110.7(3) . . ?
C7 C8 C9 114.2(3) . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C6 C1 H1 120.5 . . ?
C2 C1 C6 118.9(3) . . ?
C2 C1 H1 120.5 . . ?
C11 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C9 C10 C11 115.6(3) . . ?
C9 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C4 C3 C2 120.7(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.2(3) . . ?
C17 C16 H16 120.4 . . ?
C1 C2 C3 121.2(4) . . ?
C1 C2 H2A 119.4 . . ?
C3 C2 H2A 119.4 . . ?
C5 C4 H4 120.8 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 H4 120.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 C17 O2 120.0(3) . . ?
C16 C17 C18 120.8(3) . . ?
C18 C17 O2 119.0(3) . . ?
C14 C19 H19 119.3 . . ?
C18 C19 C14 121.3(3) . . ?
C18 C19 H19 119.3 . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.3(3) . . ?
C19 C18 H18 120.4 . . ?
O2 C20 F2 111.0(7) . . ?
O2 C20 F3 107.9(6) . . ?
F2 C20 F3 106.0(5) . . ?
F1 C20 O2 115.9(5) . . ?
F1 C20 F2 107.3(6) . . ?
F1 C20 F3 108.4(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
