# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2153291'
loop_
_audit_author_name
_audit_author_address
'Jinyun Luo'
;SHIHEZI University 
China
;
_audit_update_record             
;
2022-02-19 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;
_audit_creation_date             2021-04-14
_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         'C27 H20 O3 S2'
_chemical_formula_sum            'C27 H20 O3 S2'
_chemical_formula_weight         456.55
_chemical_absolute_configuration ?
_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'
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      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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.5368(2)
_cell_length_b                   11.7485(3)
_cell_length_c                   22.2440(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2230.95(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9659
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.85
_cell_measurement_theta_min      4.26
_shelx_estimated_absorpt_T_max   0.814
_shelx_estimated_absorpt_T_min   0.731
_exptl_absorpt_coefficient_mu    2.383
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            49617
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.127
_diffrn_reflns_theta_min         4.256
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4194
_reflns_number_total             4400
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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         0.167
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.041(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0316P)²+0.5722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0711
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C17(H17), C18(H18), C23(H23), C2(H2), C6(H6), C19(H19),
 C27(H27), C13(H13), C4(H4), C5(H5), C11(H11), C21(H21), C3(H3), C20(H20),
 C25(H25), C26(H26), C12(H12), C24(H24)
;
_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 -0.68707(7) -0.61683(5) -0.29005(3) 0.02943(14) Uani 1 1 d . . . . .
S2 S -0.20908(7) -0.49625(6) -0.31245(3) 0.03492(15) Uani 1 1 d . . . . .
O2 O -0.7214(2) -0.61981(17) -0.35334(8) 0.0385(4) Uani 1 1 d . . . . .
O1 O -0.7039(2) -0.72026(15) -0.25590(8) 0.0394(4) Uani 1 1 d . . . . .
O3 O -0.5249(2) -0.44415(18) -0.41062(9) 0.0443(5) Uani 1 1 d . . . . .
C8 C -0.4440(3) -0.5608(2) -0.21506(11) 0.0279(5) Uani 1 1 d . . . . .
C9 C -0.4278(3) -0.4563(2) -0.18664(12) 0.0343(5) Uani 1 1 d . . . . .
H9 H -0.447707 -0.388006 -0.208178 0.041 Uiso 1 1 calc R . . . .
C1 C -0.8029(3) -0.5113(2) -0.25475(10) 0.0292(5) Uani 1 1 d . . . . .
C15 C -0.4563(3) -0.5268(2) -0.39180(11) 0.0312(5) Uani 1 1 d . . . . .
C7 C -0.4946(3) -0.5645(2) -0.27930(10) 0.0273(5) Uani 1 1 d . . . . .
C16 C -0.4056(3) -0.6233(2) -0.43023(10) 0.0300(5) Uani 1 1 d . . . . .
C10 C -0.3825(3) -0.4515(3) -0.12681(12) 0.0429(7) Uani 1 1 d . . . . .
H10 H -0.371811 -0.379846 -0.107469 0.051 Uiso 1 1 calc R . . . .
C14 C -0.4070(3) -0.5310(2) -0.32607(10) 0.0286(5) Uani 1 1 d . . . . .
C22 C -0.1508(3) -0.4120(2) -0.37542(11) 0.0317(5) Uani 1 1 d . . . . .
C17 C -0.3431(3) -0.7222(2) -0.40609(11) 0.0375(6) Uani 1 1 d . . . . .
H17 H -0.330189 -0.728533 -0.363804 0.045 Uiso 1 1 calc R . . . .
C18 C -0.2992(4) -0.8119(3) -0.44284(12) 0.0460(7) Uani 1 1 d . . . . .
H18 H -0.257395 -0.879519 -0.425795 0.055 Uiso 1 1 calc R . . . .
C23 C -0.0244(3) -0.4490(3) -0.40862(12) 0.0428(6) Uani 1 1 d . . . . .
H23 H 0.018682 -0.522402 -0.401597 0.051 Uiso 1 1 calc R . . . .
C2 C -0.8768(3) -0.5376(2) -0.20123(11) 0.0357(6) Uani 1 1 d . . . . .
H2 H -0.867110 -0.611157 -0.183932 0.043 Uiso 1 1 calc R . . . .
C6 C -0.8120(3) -0.4043(2) -0.28048(11) 0.0349(5) Uani 1 1 d . . . . .
H6 H -0.760048 -0.388201 -0.317276 0.042 Uiso 1 1 calc R . . . .
C19 C -0.3166(4) -0.8026(3) -0.50435(12) 0.0452(7) Uani 1 1 d . . . . .
H19 H -0.285795 -0.863531 -0.529799 0.054 Uiso 1 1 calc R . . . .
C27 C -0.2169(4) -0.3070(2) -0.38590(12) 0.0414(6) Uani 1 1 d . . . . .
H27 H -0.303662 -0.281649 -0.362748 0.050 Uiso 1 1 calc R . . . .
C13 C -0.4158(3) -0.6598(2) -0.18268(13) 0.0381(6) Uani 1 1 d . . . . .
H13 H -0.428730 -0.731751 -0.201529 0.046 Uiso 1 1 calc R . . . .
C4 C -0.9746(4) -0.3464(3) -0.19805(12) 0.0470(8) Uani 1 1 d . . . . .
H4 H -1.033736 -0.289111 -0.178231 0.056 Uiso 1 1 calc R . . . .
C5 C -0.8985(3) -0.3214(2) -0.25139(13) 0.0424(7) Uani 1 1 d . . . . .
H5 H -0.905759 -0.247136 -0.268044 0.051 Uiso 1 1 calc R . . . .
C11 C -0.3532(4) -0.5496(3) -0.09545(12) 0.0464(7) Uani 1 1 d . . . . .
H11 H -0.321682 -0.545651 -0.054535 0.056 Uiso 1 1 calc R . . . .
C21 C -0.4236(3) -0.6151(3) -0.49236(11) 0.0407(6) Uani 1 1 d . . . . .
H21 H -0.466481 -0.548074 -0.509643 0.049 Uiso 1 1 calc R . . . .
C3 C -0.9653(3) -0.4541(3) -0.17345(12) 0.0464(7) Uani 1 1 d . . . . .
H3 H -1.019847 -0.470912 -0.137303 0.056 Uiso 1 1 calc R . . . .
C20 C -0.3789(4) -0.7047(3) -0.52878(12) 0.0480(8) Uani 1 1 d . . . . .
H20 H -0.391133 -0.698748 -0.571106 0.058 Uiso 1 1 calc R . . . .
C25 C -0.0253(4) -0.2743(3) -0.46369(14) 0.0578(9) Uani 1 1 d . . . . .
H25 H 0.018270 -0.226707 -0.493888 0.069 Uiso 1 1 calc R . . . .
C26 C -0.1541(4) -0.2383(3) -0.43126(14) 0.0527(8) Uani 1 1 d . . . . .
H26 H -0.200280 -0.166549 -0.439816 0.063 Uiso 1 1 calc R . . . .
C12 C -0.3692(4) -0.6544(3) -0.12324(14) 0.0480(7) Uani 1 1 d . . . . .
H12 H -0.348310 -0.722330 -0.101535 0.058 Uiso 1 1 calc R . . . .
C24 C 0.0398(4) -0.3789(4) -0.45228(14) 0.0581(9) Uani 1 1 d . . . . .
H24 H 0.128966 -0.403334 -0.474342 0.070 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 O2 1.4384(18) . ?
S1 O1 1.4403(19) . ?
S1 C1 1.769(2) . ?
S1 C7 1.771(2) . ?
S2 C14 1.764(2) . ?
S2 C22 1.786(3) . ?
O3 C15 1.209(3) . ?
C8 C9 1.387(3) . ?
C8 C7 1.494(3) . ?
C8 C13 1.389(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(4) . ?
C1 C2 1.382(3) . ?
C1 C6 1.383(3) . ?
C15 C16 1.484(4) . ?
C15 C14 1.522(3) . ?
C7 C14 1.340(3) . ?
C16 C17 1.387(4) . ?
C16 C21 1.394(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.370(4) . ?
C22 C23 1.379(4) . ?
C22 C27 1.376(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.384(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.384(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.378(5) . ?
C27 H27 0.9500 . ?
C27 C26 1.399(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.382(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(4) . ?
C4 C3 1.380(5) . ?
C5 H5 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.385(4) . ?
C21 H21 0.9500 . ?
C21 C20 1.382(4) . ?
C3 H3 0.9500 . ?
C20 H20 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.382(5) . ?
C25 C24 1.372(5) . ?
C26 H26 0.9500 . ?
C12 H12 0.9500 . ?
C24 H24 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
O2 S1 O1 118.39(12) . . ?
O2 S1 C1 109.72(11) . . ?
O2 S1 C7 109.26(11) . . ?
O1 S1 C1 107.54(12) . . ?
O1 S1 C7 108.32(12) . . ?
C1 S1 C7 102.43(11) . . ?
C14 S2 C22 105.08(12) . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 C13 119.2(2) . . ?
C13 C8 C7 121.5(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
C2 C1 S1 118.8(2) . . ?
C2 C1 C6 122.2(2) . . ?
C6 C1 S1 118.97(18) . . ?
O3 C15 C16 123.7(2) . . ?
O3 C15 C14 119.5(2) . . ?
C16 C15 C14 116.6(2) . . ?
C8 C7 S1 114.07(17) . . ?
C14 C7 S1 121.00(18) . . ?
C14 C7 C8 124.9(2) . . ?
C17 C16 C15 121.9(2) . . ?
C17 C16 C21 118.9(3) . . ?
C21 C16 C15 119.1(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C15 C14 S2 115.00(17) . . ?
C7 C14 S2 117.97(18) . . ?
C7 C14 C15 126.9(2) . . ?
C23 C22 S2 117.6(2) . . ?
C27 C22 S2 121.0(2) . . ?
C27 C22 C23 120.9(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.2 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.8(3) . . ?
C24 C23 H23 120.1 . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C6 H6 120.8 . . ?
C1 C6 C5 118.5(2) . . ?
C5 C6 H6 120.8 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C22 C27 H27 120.6 . . ?
C22 C27 C26 118.8(3) . . ?
C26 C27 H27 120.6 . . ?
C8 C13 H13 119.8 . . ?
C12 C13 C8 120.5(3) . . ?
C12 C13 H13 119.8 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.5(3) . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.1(2) . . ?
C12 C11 H11 119.9 . . ?
C16 C21 H21 120.0 . . ?
C20 C21 C16 119.9(3) . . ?
C20 C21 H21 120.0 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C19 C20 C21 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.0(3) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 C27 120.3(3) . . ?
C25 C26 H26 119.8 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H24 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_11_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2195981'
loop_
_audit_author_name
_audit_author_address
'jinyun luo'
;SHIHEZI UNIVERSITY
China
;
_audit_update_record             
;
2022-08-10 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;
_audit_creation_date             2022-04-04
_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         'C23 H16 F3 N O5 S2'
_chemical_formula_sum            'C23 H16 F3 N O5 S2'
_chemical_formula_weight         507.49
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3165(7)
_cell_length_b                   11.1602(9)
_cell_length_c                   11.5520(7)
_cell_angle_alpha                82.618(5)
_cell_angle_beta                 70.573(4)
_cell_angle_gamma                63.536(5)
_cell_volume                     1122.57(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2666
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.98
_cell_measurement_theta_min      4.06
_shelx_estimated_absorpt_T_max   0.755
_shelx_estimated_absorpt_T_min   0.703
_exptl_absorpt_coefficient_mu    2.709
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1194 before and 0.0829 after correction. The Ratio of minimum to maximum transmission is 0.6652. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.0716
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11762
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.495
_diffrn_reflns_theta_max         67.495
_diffrn_reflns_theta_min         4.059
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2047
_reflns_number_total             3993
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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         0.717
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3993
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.0896
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1729P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2649
_refine_ls_wR_factor_ref         0.3307
_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.a Riding coordinates:
 C14(H14A,H14B,H14C)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C9(H9), C10(H10), C12(H12),
 C18(H18), C19(H19), C21(H21), C22(H22)
2.c Fitted hexagon refined as free rotating group:
 C13(C8,C9,C10,C11,C12)
;
_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
C1 C 0.7983(7) 0.6697(6) 0.5369(6) 0.0844(17) Uani 1 1 d . . . . .
C2 C 0.9028(7) 0.6513(7) 0.4212(7) 0.0918(19) Uani 1 1 d . . . . .
H2 H 0.910083 0.596685 0.362784 0.110 Uiso 1 1 calc R . . . .
C3 C 0.9969(8) 0.7162(8) 0.3940(7) 0.100(2) Uani 1 1 d . . . . .
H3 H 1.066539 0.707214 0.316079 0.120 Uiso 1 1 calc R . . . .
C4 C 0.9863(9) 0.7956(8) 0.4849(9) 0.105(2) Uani 1 1 d . . . . .
H4 H 1.049883 0.838391 0.467301 0.126 Uiso 1 1 calc R . . . .
C5 C 0.8814(9) 0.8103(8) 0.6009(8) 0.104(2) Uani 1 1 d . . . . .
H5 H 0.874568 0.862745 0.660955 0.125 Uiso 1 1 calc R . . . .
C6 C 0.7859(8) 0.7460(7) 0.6269(7) 0.0898(18) Uani 1 1 d . . . . .
H6 H 0.715208 0.754948 0.704227 0.108 Uiso 1 1 calc R . . . .
C7 C 0.4956(6) 0.7276(6) 0.5741(6) 0.0770(15) Uani 1 1 d . . . . .
C13 C 0.4038(5) 0.7381(4) 0.4007(4) 0.098(2) Uani 1 1 d . . . . .
H13 H 0.365450 0.677568 0.441167 0.118 Uiso 1 1 calc R . . . .
C8 C 0.4807(5) 0.7798(4) 0.4530(3) 0.0808(17) Uani 1 1 d G . . . .
C9 C 0.5380(5) 0.8702(5) 0.3925(4) 0.098(2) Uani 1 1 d G . . . .
H9 H 0.589422 0.898091 0.427529 0.118 Uiso 1 1 calc R . . . .
C10 C 0.5184(6) 0.9189(5) 0.2796(4) 0.112(2) Uani 1 1 d G . . . .
H10 H 0.556723 0.979413 0.239124 0.134 Uiso 1 1 calc R . . . .
C11 C 0.4415(6) 0.8772(6) 0.2273(3) 0.120(3) Uani 1 1 d G . . . .
C12 C 0.3842(6) 0.7868(6) 0.2878(4) 0.121(3) Uani 1 1 d G . . . .
H12 H 0.332751 0.758892 0.252759 0.145 Uiso 1 1 calc R . . . .
C14 C 0.4026(14) 0.9277(14) 0.1088(9) 0.164(5) Uani 1 1 d . . . . .
H14A H 0.341605 1.022804 0.115720 0.246 Uiso 1 1 d R . . . .
H14B H 0.495715 0.907644 0.042560 0.246 Uiso 1 1 d R . . . .
H14C H 0.347645 0.884644 0.093000 0.246 Uiso 1 1 d R . . . .
C15 C 0.3825(7) 0.7678(6) 0.6812(5) 0.0806(16) Uani 1 1 d . . . . .
C16 C 0.3899(8) 0.7161(7) 0.8083(6) 0.0852(17) Uani 1 1 d . . . . .
C17 C 0.3340(7) 0.6135(6) 0.8588(6) 0.0827(17) Uani 1 1 d . . . . .
C18 C 0.2943(8) 0.5536(7) 0.7880(6) 0.0890(18) Uani 1 1 d . . . . .
H18 H 0.304203 0.576921 0.706335 0.107 Uiso 1 1 calc R . . . .
C19 C 0.2395(8) 0.4586(8) 0.8372(6) 0.0942(19) Uani 1 1 d . . . . .
H19 H 0.212479 0.418202 0.789411 0.113 Uiso 1 1 calc R . . . .
C20 C 0.2262(7) 0.4255(7) 0.9593(6) 0.0898(18) Uani 1 1 d . . . . .
C21 C 0.2651(8) 0.4859(8) 1.0323(6) 0.097(2) Uani 1 1 d . . . . .
H21 H 0.254834 0.463239 1.114103 0.116 Uiso 1 1 calc R . . . .
C22 C 0.3184(7) 0.5787(8) 0.9817(6) 0.0898(19) Uani 1 1 d . . . . .
H22 H 0.344747 0.619573 1.029614 0.108 Uiso 1 1 calc R . . . .
C23 C 0.1023(9) 0.9650(9) 0.8128(9) 0.113(3) Uani 1 1 d . . . . .
F1 F 0.1626(7) 1.0289(6) 0.8512(6) 0.162(2) Uani 1 1 d . . . . .
F2 F 0.0787(6) 0.8843(5) 0.9036(5) 0.1358(19) Uani 1 1 d . . . . .
F3 F -0.0340(6) 1.0564(6) 0.8104(5) 0.149(2) Uani 1 1 d . . . . .
N1 N 0.1660(7) 0.3256(7) 1.0100(7) 0.1050(18) Uani 1 1 d . . . . .
O1 O 0.7206(5) 0.5051(5) 0.4714(4) 0.0927(13) Uani 1 1 d . . . . .
O2 O 0.6618(5) 0.5389(4) 0.6941(4) 0.0865(12) Uani 1 1 d . . . . .
O3 O 0.4352(6) 0.7665(5) 0.8649(4) 0.0983(14) Uani 1 1 d . . . . .
O4 O 0.1619(10) 0.2926(9) 1.1158(7) 0.160(3) Uani 1 1 d . . . . .
O5 O 0.1175(8) 0.2869(7) 0.9499(6) 0.134(2) Uani 1 1 d . . . . .
S1 S 0.67510(17) 0.59156(16) 0.57221(14) 0.0814(5) Uani 1 1 d . . . . .
S2 S 0.2045(2) 0.8917(2) 0.66690(19) 0.1111(8) 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
C1 C2 1.380(10) . ?
C1 C6 1.365(10) . ?
C1 S1 1.759(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.405(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.397(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.474(6) . ?
C7 C15 1.345(9) . ?
C7 S1 1.792(5) . ?
C13 H13 0.9300 . ?
C13 C8 1.3900 . ?
C13 C12 1.3900 . ?
C8 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C10 1.3900 . ?
C10 H10 0.9300 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C11 C14 1.521(9) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9601 . ?
C14 H14C 0.9599 . ?
C15 C16 1.520(8) . ?
C15 S2 1.786(6) . ?
C16 C17 1.476(10) . ?
C16 O3 1.223(8) . ?
C17 C18 1.375(9) . ?
C17 C22 1.397(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(10) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(9) . ?
C20 C21 1.392(11) . ?
C20 N1 1.477(10) . ?
C21 H21 0.9300 . ?
C21 C22 1.362(10) . ?
C22 H22 0.9300 . ?
C23 F1 1.324(11) . ?
C23 F2 1.323(10) . ?
C23 F3 1.327(9) . ?
C23 S2 1.739(10) . ?
N1 O4 1.223(9) . ?
N1 O5 1.192(9) . ?
O1 S1 1.424(5) . ?
O2 S1 1.441(4) . ?

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
C2 C1 S1 119.3(6) . . ?
C6 C1 C2 122.9(7) . . ?
C6 C1 S1 117.7(6) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.6(7) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(8) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(8) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.7(8) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 118.9(7) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C8 C7 S1 115.6(4) . . ?
C15 C7 C8 124.8(5) . . ?
C15 C7 S1 119.4(4) . . ?
C8 C13 H13 120.0 . . ?
C8 C13 C12 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C8 C7 118.0(4) . . ?
C9 C8 C7 122.0(4) . . ?
C9 C8 C13 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 C14 126.1(6) . . ?
C12 C11 C14 113.8(6) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C11 C14 H14A 109.6 . . ?
C11 C14 H14B 108.6 . . ?
C11 C14 H14C 110.2 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 C16 127.2(5) . . ?
C7 C15 S2 114.4(4) . . ?
C16 C15 S2 118.3(4) . . ?
C17 C16 C15 118.1(6) . . ?
O3 C16 C15 118.0(6) . . ?
O3 C16 C17 123.7(6) . . ?
C18 C17 C16 121.2(6) . . ?
C18 C17 C22 119.5(7) . . ?
C22 C17 C16 119.2(6) . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.7(6) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 120.8 . . ?
C20 C19 C18 118.4(7) . . ?
C20 C19 H19 120.8 . . ?
C19 C20 C21 121.5(7) . . ?
C19 C20 N1 117.5(7) . . ?
C21 C20 N1 121.0(7) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 C20 118.8(6) . . ?
C22 C21 H21 120.6 . . ?
C17 C22 H22 119.5 . . ?
C21 C22 C17 121.0(6) . . ?
C21 C22 H22 119.5 . . ?
F1 C23 F3 105.9(8) . . ?
F1 C23 S2 114.7(7) . . ?
F2 C23 F1 104.2(8) . . ?
F2 C23 F3 106.5(7) . . ?
F2 C23 S2 116.7(7) . . ?
F3 C23 S2 108.1(7) . . ?
O4 N1 C20 116.7(7) . . ?
O5 N1 C20 119.5(7) . . ?
O5 N1 O4 123.6(8) . . ?
C1 S1 C7 103.1(3) . . ?
O1 S1 C1 107.9(3) . . ?
O1 S1 C7 107.2(3) . . ?
O1 S1 O2 119.6(3) . . ?
O2 S1 C1 109.5(3) . . ?
O2 S1 C7 108.3(3) . . ?
C23 S2 C15 104.5(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
