# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yd246_0m
_database_code_depnum_ccdc_archive 'CCDC 2036972'
loop_
_audit_author_name
_audit_author_address
'Chuanle Chuanle Zhu'
;South China University of Technology
China
;
_audit_update_record             
;
2020-10-14 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;
_audit_creation_date             2020-10-07
_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         'C18 H20 F N3 O6 S2'
_chemical_formula_sum            'C18 H20 F N3 O6 S2'
_chemical_formula_weight         457.49
_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 0.0033 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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.3919(6)
_cell_length_b                   13.7713(13)
_cell_length_c                   23.551(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.388(3)
_cell_angle_gamma                90
_cell_volume                     2067.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6392
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.123
_cell_measurement_theta_min      2.994
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1357 before and 0.0714 after correction. The Ratio of minimum to maximum transmission is 0.8652. 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    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22873
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.447
_diffrn_reflns_theta_min         2.279
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  '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                2956
_reflns_number_total             4207
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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         0.655
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.100
_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     274
_refine_ls_number_reflns         4207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0757
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0986P)²+7.5185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2276
_refine_ls_wR_factor_ref         0.2505
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C2(H2), C6(H6), C11(H11), C15(H15), C12(H12), C13(H13),
 C14(H14)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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 0.2862(2) 0.34033(9) 0.43014(6) 0.0446(4) Uani 1 1 d . . . . .
S2 S 0.7738(3) 0.49247(11) 0.20013(6) 0.0517(4) Uani 1 1 d . . . . .
F1 F 0.7124(5) 0.2672(2) 0.38368(14) 0.0545(8) Uani 1 1 d . . . . .
O3 O 0.2144(6) 0.3549(3) 0.37200(19) 0.0628(12) Uani 1 1 d . . . . .
O2 O 0.2415(6) -0.1164(3) 0.5200(2) 0.0599(11) Uani 1 1 d . . . . .
O4 O 0.1858(7) 0.3863(3) 0.4748(2) 0.0643(12) Uani 1 1 d . . . . .
N2 N 0.5319(6) 0.3764(3) 0.43581(17) 0.0379(9) Uani 1 1 d . . . . .
O5 O 0.7082(9) 0.4571(3) 0.14484(17) 0.0751(14) Uani 1 1 d . . . . .
N1 N 0.2445(6) -0.0871(3) 0.4708(2) 0.0481(11) Uani 1 1 d . . . . .
N3 N 0.7013(7) 0.4148(3) 0.24625(17) 0.0443(10) Uani 1 1 d . . . . .
O1 O 0.2319(8) -0.1405(3) 0.4288(2) 0.0695(13) Uani 1 1 d . . . . .
O6 O 0.9912(8) 0.5119(4) 0.2139(2) 0.0788(15) Uani 1 1 d . . . . .
C10 C 0.6432(8) 0.5311(4) 0.3550(2) 0.0405(11) Uani 1 1 d . . . . .
C4 C 0.2815(7) 0.2128(4) 0.4425(2) 0.0394(11) Uani 1 1 d . . . . .
C1 C 0.2604(7) 0.0184(3) 0.4611(2) 0.0375(11) Uani 1 1 d . . . . .
C16 C 0.8235(8) 0.3981(4) 0.3007(2) 0.0392(11) Uani 1 1 d . . . . .
H16A H 0.954678 0.436462 0.301822 0.047 Uiso 1 1 calc R . . . .
H16B H 0.861991 0.328572 0.304012 0.047 Uiso 1 1 calc R . . . .
C9 C 0.6990(7) 0.4269(4) 0.3510(2) 0.0366(10) Uani 1 1 d . . . . .
C3 C 0.2560(7) 0.1791(4) 0.4973(2) 0.0397(11) Uani 1 1 d . . . . .
H3 H 0.244804 0.223510 0.527838 0.048 Uiso 1 1 calc R . . . .
C8 C 0.6483(8) 0.3621(3) 0.3884(2) 0.0373(11) Uani 1 1 d . . . . .
C7 C 0.6496(9) 0.3732(4) 0.4928(2) 0.0452(12) Uani 1 1 d . . . . .
H7A H 0.553734 0.387359 0.522318 0.068 Uiso 1 1 calc GR . . . .
H7B H 0.761973 0.421760 0.494435 0.068 Uiso 1 1 calc GR . . . .
H7C H 0.710429 0.308476 0.499270 0.068 Uiso 1 1 calc GR . . . .
C5 C 0.2996(8) 0.1493(4) 0.3982(2) 0.0455(12) Uani 1 1 d . . . . .
H5 H 0.319739 0.173530 0.361264 0.055 Uiso 1 1 calc R . . . .
C2 C 0.2471(7) 0.0802(4) 0.5067(2) 0.0398(11) Uani 1 1 d . . . . .
H2 H 0.232137 0.055364 0.543823 0.048 Uiso 1 1 calc R . . . .
C6 C 0.2887(8) 0.0509(4) 0.4071(2) 0.0452(12) Uani 1 1 d . . . . .
H6 H 0.300354 0.006486 0.376623 0.054 Uiso 1 1 calc R . . . .
C11 C 0.4400(9) 0.5646(4) 0.3444(3) 0.0523(14) Uani 1 1 d . . . . .
H11 H 0.328156 0.519830 0.336905 0.063 Uiso 1 1 calc R . . . .
C15 C 0.8026(10) 0.5985(4) 0.3667(2) 0.0495(13) Uani 1 1 d . . . . .
H15 H 0.942486 0.576636 0.375138 0.059 Uiso 1 1 calc R . . . .
C17 C 0.4986(10) 0.3642(5) 0.2368(3) 0.0601(16) Uani 1 1 d . . . . .
H17A H 0.412759 0.377511 0.268662 0.090 Uiso 1 1 calc GR . . . .
H17B H 0.522895 0.294095 0.234207 0.090 Uiso 1 1 calc GR . . . .
H17C H 0.425254 0.387220 0.201292 0.090 Uiso 1 1 calc GR . . . .
C12 C 0.3994(11) 0.6637(5) 0.3449(3) 0.0672(18) Uani 1 1 d . . . . .
H12 H 0.259149 0.685901 0.337670 0.081 Uiso 1 1 calc R . . . .
C13 C 0.5575(13) 0.7305(4) 0.3554(3) 0.0684(19) Uani 1 1 d . . . . .
H13 H 0.527529 0.798060 0.355378 0.082 Uiso 1 1 calc R . . . .
C14 C 0.7598(12) 0.6976(4) 0.3660(3) 0.0635(18) Uani 1 1 d . . . . .
H14 H 0.871046 0.742841 0.372978 0.076 Uiso 1 1 calc R . . . .
C18 C 0.6323(13) 0.6002(4) 0.2092(3) 0.0665(18) Uani 1 1 d . . . . .
H18A H 0.653226 0.644690 0.177661 0.100 Uiso 1 1 calc GR . . . .
H18B H 0.682244 0.630964 0.245282 0.100 Uiso 1 1 calc GR . . . .
H18C H 0.482678 0.585103 0.209804 0.100 Uiso 1 1 calc GR . . . .


_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 O3 1.425(4) . ?
S1 O4 1.423(4) . ?
S1 N2 1.642(4) . ?
S1 C4 1.781(5) . ?
S2 O5 1.423(4) . ?
S2 N3 1.617(4) . ?
S2 O6 1.428(5) . ?
S2 C18 1.760(6) . ?
F1 C8 1.378(6) . ?
O2 N1 1.227(6) . ?
N2 C8 1.402(6) . ?
N2 C7 1.489(6) . ?
N1 O1 1.232(7) . ?
N1 C1 1.475(6) . ?
N3 C16 1.468(6) . ?
N3 C17 1.473(7) . ?
C10 C9 1.484(7) . ?
C10 C11 1.383(7) . ?
C10 C15 1.390(7) . ?
C4 C3 1.393(7) . ?
C4 C5 1.373(8) . ?
C1 C2 1.378(7) . ?
C1 C6 1.375(7) . ?
C16 C9 1.528(7) . ?
C9 C8 1.311(7) . ?
C3 C2 1.382(7) . ?
C5 C6 1.373(8) . ?
C11 C12 1.390(8) . ?
C15 C14 1.392(8) . ?
C12 C13 1.374(10) . ?
C13 C14 1.375(10) . ?

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
O3 S1 N2 105.7(2) . . ?
O3 S1 C4 106.7(3) . . ?
O4 S1 O3 121.2(3) . . ?
O4 S1 N2 106.7(3) . . ?
O4 S1 C4 107.7(2) . . ?
N2 S1 C4 108.2(2) . . ?
O5 S2 N3 108.0(3) . . ?
O5 S2 O6 119.0(3) . . ?
O5 S2 C18 106.4(3) . . ?
N3 S2 C18 107.5(3) . . ?
O6 S2 N3 107.2(3) . . ?
O6 S2 C18 108.3(4) . . ?
C8 N2 S1 117.1(3) . . ?
C8 N2 C7 116.9(4) . . ?
C7 N2 S1 118.6(3) . . ?
O2 N1 O1 123.8(5) . . ?
O2 N1 C1 118.4(5) . . ?
O1 N1 C1 117.7(5) . . ?
C16 N3 S2 122.0(4) . . ?
C16 N3 C17 117.4(4) . . ?
C17 N3 S2 120.3(4) . . ?
C11 C10 C9 122.5(5) . . ?
C11 C10 C15 118.5(5) . . ?
C15 C10 C9 118.8(5) . . ?
C3 C4 S1 119.0(4) . . ?
C5 C4 S1 120.0(4) . . ?
C5 C4 C3 121.0(5) . . ?
C2 C1 N1 118.6(5) . . ?
C6 C1 N1 118.7(5) . . ?
C6 C1 C2 122.7(5) . . ?
N3 C16 C9 111.3(4) . . ?
C10 C9 C16 116.3(4) . . ?
C8 C9 C10 122.8(4) . . ?
C8 C9 C16 120.9(4) . . ?
C2 C3 C4 119.1(5) . . ?
F1 C8 N2 112.1(4) . . ?
C9 C8 F1 120.0(4) . . ?
C9 C8 N2 127.8(5) . . ?
C6 C5 C4 120.3(5) . . ?
C1 C2 C3 118.6(5) . . ?
C5 C6 C1 118.3(5) . . ?
C10 C11 C12 119.9(6) . . ?
C10 C15 C14 120.8(6) . . ?
C13 C12 C11 121.6(6) . . ?
C12 C13 C14 118.7(6) . . ?
C13 C14 C15 120.4(6) . . ?

_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_zh_0m
_database_code_depnum_ccdc_archive 'CCDC 2036948'
loop_
_audit_author_name
_audit_author_address
'Chuanle Zhu'
;South China University of Technology
China
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2022-01-24 downloaded from the CCDC.
;
_audit_creation_date             2019-11-05
_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         'C25 H23 F N2 O2 S'
_chemical_formula_sum            'C25 H23 F N2 O2 S'
_chemical_formula_weight         434.51
_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      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                   10.5052(14)
_cell_length_b                   10.7663(14)
_cell_length_c                   11.1339(15)
_cell_angle_alpha                96.383(5)
_cell_angle_beta                 108.432(5)
_cell_angle_gamma                110.430(4)
_cell_volume                     1084.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5506
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.329
_cell_measurement_theta_min      2.237
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1480 before and 0.0467 after correction. The Ratio of minimum to maximum transmission is 0.9171. 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    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12498
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.238
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  '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                3563
_reflns_number_total             4389
_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         0.252
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.030
_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)+(0.0427P)²+0.4325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1042
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C20(H20), C23(H23), C2(H2), C21(H21), C8(H8), C12(H12), C7(H7),
 C3(H3), C5(H5), C4(H4), C16(H16), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C25(H25A,H25B,H25C)
;
_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 0.78460(5) 0.26046(4) 0.76042(4) 0.02887(13) Uani 1 1 d . . . . .
F1 F 0.51116(11) 0.15118(11) 0.40001(10) 0.0381(3) Uani 1 1 d . . . . .
O1 O 0.91720(14) 0.37912(13) 0.79026(13) 0.0392(3) Uani 1 1 d . . . . .
O2 O 0.75624(14) 0.13699(13) 0.67354(12) 0.0360(3) Uani 1 1 d . . . . .
N1 N 0.64892(16) 0.30555(14) 0.69599(14) 0.0292(3) Uani 1 1 d . . . . .
N2 N 0.31025(16) 0.18639(15) 0.28891(14) 0.0313(3) Uani 1 1 d . . . . .
C19 C 0.77748(18) 0.22357(17) 0.90934(17) 0.0280(4) Uani 1 1 d . . . . .
C24 C 0.69381(19) 0.09155(17) 0.90997(18) 0.0306(4) Uani 1 1 d . . . . .
H24 H 0.640574 0.021607 0.830871 0.037 Uiso 1 1 calc R . . . .
C10 C 0.39937(19) 0.22193(17) 0.52642(17) 0.0290(4) Uani 1 1 d . . . . .
C20 C 0.8530(2) 0.32631(18) 1.02478(18) 0.0347(4) Uani 1 1 d . . . . .
H20 H 0.908769 0.417055 1.024118 0.042 Uiso 1 1 calc R . . . .
C9 C 0.40516(19) 0.19103(18) 0.41028(17) 0.0298(4) Uani 1 1 d . . . . .
C17 C 0.49905(19) 0.19467(18) 0.64188(17) 0.0307(4) Uani 1 1 d . . . . .
H17A H 0.457732 0.187252 0.710625 0.037 Uiso 1 1 calc R . . . .
H17B H 0.504163 0.106493 0.614187 0.037 Uiso 1 1 calc R . . . .
C23 C 0.6886(2) 0.06271(18) 1.02685(19) 0.0344(4) Uani 1 1 d . . . . .
H23 H 0.631600 -0.027794 1.027115 0.041 Uiso 1 1 calc R . . . .
C1 C 0.3477(2) 0.23744(17) 0.18897(17) 0.0307(4) Uani 1 1 d . . . . .
C11 C 0.2948(2) 0.28015(19) 0.54302(17) 0.0314(4) Uani 1 1 d . . . . .
C22 C 0.7648(2) 0.16302(19) 1.14351(18) 0.0342(4) Uani 1 1 d . . . . .
C2 C 0.4848(2) 0.30160(18) 0.18281(19) 0.0363(4) Uani 1 1 d . . . . .
H2 H 0.572879 0.318511 0.253798 0.044 Uiso 1 1 calc R . . . .
C21 C 0.8465(2) 0.29569(19) 1.14028(19) 0.0379(4) Uani 1 1 d . . . . .
H21 H 0.898402 0.366070 1.219090 0.045 Uiso 1 1 calc R . . . .
C8 C 0.1569(2) 0.1295(2) 0.24652(19) 0.0380(4) Uani 1 1 d . . . . .
H8 H 0.102837 0.087263 0.295806 0.046 Uiso 1 1 calc R . . . .
C6 C 0.2158(2) 0.21171(18) 0.08531(18) 0.0355(4) Uani 1 1 d . . . . .
C12 C 0.2924(2) 0.3969(2) 0.5012(2) 0.0414(5) Uani 1 1 d . . . . .
H12 H 0.358191 0.439457 0.461346 0.050 Uiso 1 1 calc R . . . .
C7 C 0.0976(2) 0.1437(2) 0.12531(19) 0.0408(5) Uani 1 1 d . . . . .
H7 H -0.004247 0.113942 0.075171 0.049 Uiso 1 1 calc R . . . .
C18 C 0.6604(2) 0.43340(19) 0.7701(2) 0.0413(5) Uani 1 1 d . . . . .
H18A H 0.645489 0.419339 0.850988 0.062 Uiso 1 1 calc GR . . . .
H18B H 0.585201 0.460528 0.717265 0.062 Uiso 1 1 calc GR . . . .
H18C H 0.757988 0.505587 0.791586 0.062 Uiso 1 1 calc GR . . . .
C3 C 0.4869(2) 0.3396(2) 0.0689(2) 0.0449(5) Uani 1 1 d . . . . .
H3 H 0.578684 0.383291 0.061184 0.054 Uiso 1 1 calc R . . . .
C5 C 0.2223(3) 0.2521(2) -0.0284(2) 0.0449(5) Uani 1 1 d . . . . .
H5 H 0.134943 0.236320 -0.099808 0.054 Uiso 1 1 calc R . . . .
C4 C 0.3581(3) 0.3154(2) -0.0351(2) 0.0494(5) Uani 1 1 d . . . . .
H4 H 0.363675 0.343066 -0.112050 0.059 Uiso 1 1 calc R . . . .
C16 C 0.1966(2) 0.2192(3) 0.5999(2) 0.0493(6) Uani 1 1 d . . . . .
H16 H 0.195474 0.138980 0.628357 0.059 Uiso 1 1 calc R . . . .
C13 C 0.1958(3) 0.4518(2) 0.5168(2) 0.0542(6) Uani 1 1 d . . . . .
H13 H 0.195493 0.531358 0.487742 0.065 Uiso 1 1 calc R . . . .
C25 C 0.7635(3) 0.1299(2) 1.2712(2) 0.0501(5) Uani 1 1 d . . . . .
H25A H 0.667780 0.057940 1.256247 0.075 Uiso 1 1 calc GR . . . .
H25B H 0.780898 0.212088 1.332799 0.075 Uiso 1 1 calc GR . . . .
H25C H 0.840919 0.098021 1.307503 0.075 Uiso 1 1 calc GR . . . .
C14 C 0.0999(3) 0.3905(3) 0.5749(2) 0.0614(7) Uani 1 1 d . . . . .
H14 H 0.034192 0.428419 0.586659 0.074 Uiso 1 1 calc R . . . .
C15 C 0.0999(3) 0.2751(3) 0.6154(2) 0.0641(7) Uani 1 1 d . . . . .
H15 H 0.033247 0.232610 0.654435 0.077 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 O1 1.4330(13) . ?
S1 O2 1.4307(13) . ?
S1 N1 1.6418(15) . ?
S1 C19 1.7653(18) . ?
F1 C9 1.3565(19) . ?
N1 C17 1.482(2) . ?
N1 C18 1.470(2) . ?
N2 C9 1.386(2) . ?
N2 C1 1.399(2) . ?
N2 C8 1.400(2) . ?
C19 C24 1.388(2) . ?
C19 C20 1.390(2) . ?
C24 H24 0.9500 . ?
C24 C23 1.384(3) . ?
C10 C9 1.325(2) . ?
C10 C17 1.511(2) . ?
C10 C11 1.489(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.379(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C23 H23 0.9500 . ?
C23 C22 1.386(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.406(3) . ?
C11 C12 1.393(3) . ?
C11 C16 1.388(3) . ?
C22 C21 1.397(3) . ?
C22 C25 1.507(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(3) . ?
C21 H21 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.347(3) . ?
C6 C7 1.437(3) . ?
C6 C5 1.398(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(3) . ?
C7 H7 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.391(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.392(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C15 1.368(4) . ?
C15 H15 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
O1 S1 N1 106.15(8) . . ?
O1 S1 C19 107.90(8) . . ?
O2 S1 O1 119.56(8) . . ?
O2 S1 N1 107.21(8) . . ?
O2 S1 C19 108.32(8) . . ?
N1 S1 C19 107.09(8) . . ?
C17 N1 S1 116.31(11) . . ?
C18 N1 S1 115.37(12) . . ?
C18 N1 C17 114.06(14) . . ?
C9 N2 C1 127.34(15) . . ?
C9 N2 C8 124.59(15) . . ?
C1 N2 C8 108.06(15) . . ?
C24 C19 S1 119.49(14) . . ?
C24 C19 C20 120.18(16) . . ?
C20 C19 S1 120.32(13) . . ?
C19 C24 H24 120.3 . . ?
C23 C24 C19 119.42(17) . . ?
C23 C24 H24 120.3 . . ?
C9 C10 C17 118.80(15) . . ?
C9 C10 C11 120.84(16) . . ?
C11 C10 C17 120.35(14) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.58(16) . . ?
C21 C20 H20 120.2 . . ?
F1 C9 N2 111.52(14) . . ?
C10 C9 F1 119.63(16) . . ?
C10 C9 N2 128.77(16) . . ?
N1 C17 C10 111.14(14) . . ?
N1 C17 H17A 109.4 . . ?
N1 C17 H17B 109.4 . . ?
C10 C17 H17A 109.4 . . ?
C10 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C24 C23 H23 119.3 . . ?
C24 C23 C22 121.42(16) . . ?
C22 C23 H23 119.3 . . ?
N2 C1 C6 107.24(15) . . ?
C2 C1 N2 130.21(17) . . ?
C2 C1 C6 122.54(17) . . ?
C12 C11 C10 120.80(16) . . ?
C16 C11 C10 120.91(17) . . ?
C16 C11 C12 118.30(17) . . ?
C23 C22 C21 118.19(17) . . ?
C23 C22 C25 121.19(17) . . ?
C21 C22 C25 120.60(18) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 116.95(19) . . ?
C3 C2 H2 121.5 . . ?
C20 C21 C22 121.19(17) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
N2 C8 H8 125.2 . . ?
C7 C8 N2 109.69(17) . . ?
C7 C8 H8 125.2 . . ?
C1 C6 C7 107.17(17) . . ?
C5 C6 C1 118.90(18) . . ?
C5 C6 C7 133.93(19) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C8 C7 C6 107.83(17) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.7(2) . . ?
C4 C3 H3 119.2 . . ?
C6 C5 H5 120.6 . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5 120.6 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.21(19) . . ?
C5 C4 H4 119.4 . . ?
C11 C16 H16 119.8 . . ?
C11 C16 C15 120.3(2) . . ?
C15 C16 H16 119.8 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C16 C15 H15 119.6 . . ?
C14 C15 C16 120.7(2) . . ?
C14 C15 H15 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
