# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_gpt147f
_database_code_depnum_ccdc_archive 'CCDC 2474743'
loop_
_audit_author_name
_audit_author_address
'Premkumar Gnanasekaran'
;Tunghai University
Taiwan
;
_audit_update_record             
;
2025-07-22 deposited with the CCDC.	2025-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C34 H20 F4 N2 S'
_chemical_formula_sum            'C34 H20 F4 N2 S'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            ?
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         564.58

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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.3094(12)
_cell_length_b                   14.7807(7)
_cell_length_c                   6.9665(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.9151(15)
_cell_angle_gamma                90
_cell_volume                     2981.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9958
_cell_measurement_theta_min      2.314
_cell_measurement_theta_max      27.881
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6667
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34377
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.756
_diffrn_reflns_theta_max         27.899
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3562
_reflns_number_gt                3056
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0921P)²+4.1012P] 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         3562
_refine_ls_number_parameters     186
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1643
_refine_ls_wR_factor_gt          0.1532
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_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
S S 0.000000 -0.13748(5) 0.250000 0.03389(18) Uani 1 2 d S T P . .
F1 F 0.30134(5) 0.09608(14) -0.0167(3) 0.0793(5) Uani 1 1 d . . . . .
F2 F 0.10642(7) 0.42499(15) 0.7650(4) 0.1163(10) Uani 1 1 d . . . . .
N N 0.04131(5) -0.06841(11) 0.2269(2) 0.0300(3) Uani 1 1 d . . . . .
C1 C 0.02374(5) 0.01540(12) 0.2364(2) 0.0263(3) Uani 1 1 d . . . . .
C2 C 0.04843(5) 0.09791(13) 0.2237(2) 0.0283(3) Uani 1 1 d . . . . .
C3 C 0.02349(5) 0.17608(13) 0.2368(2) 0.0315(4) Uani 1 1 d . . . . .
H3A H 0.038482 0.232568 0.227853 0.038 Uiso 1 1 calc R U . . .
C4 C 0.09607(6) 0.09219(13) 0.1839(2) 0.0313(4) Uani 1 1 d . . . . .
H4A H 0.102993 0.041166 0.110612 0.038 Uiso 1 1 calc R U . . .
C5 C 0.13129(6) 0.15015(13) 0.2380(2) 0.0304(4) Uani 1 1 d . . . . .
C6 C 0.17608(6) 0.13772(14) 0.1666(3) 0.0355(4) Uani 1 1 d . . . . .
C7 C 0.17869(7) 0.09321(16) -0.0071(3) 0.0430(5) Uani 1 1 d . . . . .
H7A H 0.151124 0.072283 -0.084221 0.052 Uiso 1 1 calc R U . . .
C8 C 0.22090(8) 0.07864(18) -0.0706(4) 0.0520(6) Uani 1 1 d . . . . .
H8A H 0.222554 0.047697 -0.188885 0.062 Uiso 1 1 calc R U . . .
C9 C 0.26004(7) 0.11051(19) 0.0435(4) 0.0551(6) Uani 1 1 d . . . . .
C10 C 0.25935(7) 0.15608(19) 0.2135(4) 0.0575(6) Uani 1 1 d . . . . .
H10A H 0.287094 0.178015 0.287589 0.069 Uiso 1 1 calc R U . . .
C11 C 0.21701(7) 0.16951(17) 0.2753(3) 0.0474(5) Uani 1 1 d . . . . .
H11A H 0.215868 0.200851 0.393551 0.057 Uiso 1 1 calc R U . . .
C12 C 0.12742(5) 0.22462(12) 0.3778(3) 0.0320(4) Uani 1 1 d . . . . .
C13 C 0.11553(6) 0.20462(14) 0.5586(3) 0.0352(4) Uani 1 1 d . . . . .
H13A H 0.111879 0.143090 0.592610 0.042 Uiso 1 1 calc R U . . .
C14 C 0.10883(7) 0.27134(18) 0.6908(4) 0.0532(6) Uani 1 1 d . . . . .
H14A H 0.100936 0.256346 0.814164 0.064 Uiso 1 1 calc R U . . .
C15 C 0.11385(9) 0.35835(19) 0.6392(5) 0.0697(7) Uani 1 1 d . U . . .
C16 C 0.12673(10) 0.38289(17) 0.4658(6) 0.0745(8) Uani 1 1 d . U . . .
H16A H 0.130776 0.444845 0.436328 0.089 Uiso 1 1 calc R U . . .
C17 C 0.13390(8) 0.31507(15) 0.3319(4) 0.0537(6) Uani 1 1 d . . . . .
H17A H 0.143070 0.330775 0.211246 0.064 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
S N 1.6108(15) . ?
S N 1.6108(15) 2 ?
F1 C9 1.358(2) . ?
F2 C15 1.358(3) . ?
N C1 1.347(2) . ?
C1 C2 1.428(2) . ?
C1 C1 1.433(3) 2 ?
C2 C3 1.378(3) . ?
C2 C4 1.468(2) . ?
C3 C3 1.417(3) 2 ?
C3 H3A 0.9500 . ?
C4 C5 1.350(2) . ?
C4 H4A 0.9500 . ?
C5 C12 1.485(3) . ?
C5 C6 1.486(2) . ?
C6 C11 1.397(3) . ?
C6 C7 1.390(3) . ?
C7 C8 1.394(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.374(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.365(4) . ?
C10 C11 1.390(3) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C12 C17 1.395(3) . ?
C12 C13 1.390(3) . ?
C13 C14 1.384(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.350(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.369(5) . ?
C16 C17 1.407(4) . ?
C16 H16A 0.9500 . ?
C17 H17A 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
N S N 101.33(11) . 2 ?
C1 N S 106.19(11) . . ?
N C1 C2 125.53(14) . . ?
N C1 C1 113.14(9) . 2 ?
C2 C1 C1 121.33(9) . 2 ?
C3 C2 C1 115.66(14) . . ?
C3 C2 C4 126.23(17) . . ?
C1 C2 C4 117.94(16) . . ?
C2 C3 C3 123.01(10) . 2 ?
C2 C3 H3A 118.5 . . ?
C3 C3 H3A 118.5 2 . ?
C5 C4 C2 128.28(17) . . ?
C5 C4 H4A 115.9 . . ?
C2 C4 H4A 115.9 . . ?
C4 C5 C12 121.38(15) . . ?
C4 C5 C6 120.34(17) . . ?
C12 C5 C6 118.20(15) . . ?
C11 C6 C7 118.22(18) . . ?
C11 C6 C5 120.37(18) . . ?
C7 C6 C5 121.40(17) . . ?
C8 C7 C6 121.4(2) . . ?
C8 C7 H7A 119.3 . . ?
C6 C7 H7A 119.3 . . ?
C7 C8 C9 117.8(2) . . ?
C7 C8 H8A 121.1 . . ?
C9 C8 H8A 121.1 . . ?
C10 C9 F1 118.6(2) . . ?
C10 C9 C8 123.22(19) . . ?
F1 C9 C8 118.1(2) . . ?
C9 C10 C11 118.2(2) . . ?
C9 C10 H10A 120.9 . . ?
C11 C10 H10A 120.9 . . ?
C10 C11 C6 121.1(2) . . ?
C10 C11 H11A 119.4 . . ?
C6 C11 H11A 119.4 . . ?
C17 C12 C13 118.3(2) . . ?
C17 C12 C5 122.21(19) . . ?
C13 C12 C5 119.46(16) . . ?
C14 C13 C12 122.2(2) . . ?
C14 C13 H13A 118.9 . . ?
C12 C13 H13A 118.9 . . ?
C15 C14 C13 118.0(3) . . ?
C15 C14 H14A 121.0 . . ?
C13 C14 H14A 121.0 . . ?
C14 C15 F2 119.0(3) . . ?
C14 C15 C16 122.9(3) . . ?
F2 C15 C16 118.1(3) . . ?
C15 C16 C17 119.1(2) . . ?
C15 C16 H16A 120.5 . . ?
C17 C16 H16A 120.5 . . ?
C12 C17 C16 119.4(3) . . ?
C12 C17 H17A 120.3 . . ?
C16 C17 H17A 120.3 . . ?

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
N S N C1 -0.08(7) 2 . . . ?
S N C1 C2 179.62(12) . . . . ?
S N C1 C1 0.21(19) . . . 2 ?
N C1 C2 C3 179.91(15) . . . . ?
C1 C1 C2 C3 -0.7(2) 2 . . . ?
N C1 C2 C4 4.3(2) . . . . ?
C1 C1 C2 C4 -176.29(16) 2 . . . ?
C1 C2 C3 C3 0.6(3) . . . 2 ?
C4 C2 C3 C3 175.72(19) . . . 2 ?
C3 C2 C4 C5 33.8(3) . . . . ?
C1 C2 C4 C5 -151.17(17) . . . . ?
C2 C4 C5 C12 9.6(3) . . . . ?
C2 C4 C5 C6 -173.76(16) . . . . ?
C4 C5 C6 C11 -153.3(2) . . . . ?
C12 C5 C6 C11 23.5(3) . . . . ?
C4 C5 C6 C7 25.6(3) . . . . ?
C12 C5 C6 C7 -157.57(18) . . . . ?
C11 C6 C7 C8 1.3(3) . . . . ?
C5 C6 C7 C8 -177.6(2) . . . . ?
C6 C7 C8 C9 -0.6(4) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C7 C8 C9 F1 179.6(2) . . . . ?
F1 C9 C10 C11 -179.2(2) . . . . ?
C8 C9 C10 C11 1.1(4) . . . . ?
C9 C10 C11 C6 -0.3(4) . . . . ?
C7 C6 C11 C10 -0.9(3) . . . . ?
C5 C6 C11 C10 178.1(2) . . . . ?
C4 C5 C12 C17 -122.9(2) . . . . ?
C6 C5 C12 C17 60.3(2) . . . . ?
C4 C5 C12 C13 55.0(2) . . . . ?
C6 C5 C12 C13 -121.74(18) . . . . ?
C17 C12 C13 C14 1.7(3) . . . . ?
C5 C12 C13 C14 -176.28(17) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 F2 178.5(2) . . . . ?
C13 C14 C15 C16 -2.3(4) . . . . ?
C14 C15 C16 C17 1.8(4) . . . . ?
F2 C15 C16 C17 -179.0(2) . . . . ?
C13 C12 C17 C16 -2.2(3) . . . . ?
C5 C12 C17 C16 175.79(18) . . . . ?
C15 C16 C17 C12 0.5(4) . . . . ?

_refine_diff_density_max         0.506
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.051



_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_155_a_pl
_database_code_depnum_ccdc_archive 'CCDC 2474744'
loop_
_audit_author_name
_audit_author_address
'Premkumar Gnanasekaran'
;Tunghai University
Taiwan
;
_audit_update_record             
;
2025-07-22 deposited with the CCDC.	2025-10-10 downloaded from the CCDC.
;
_audit_creation_date             2024-08-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 N2 S'
_chemical_formula_sum            'C22 H16 N2 S'
_chemical_formula_weight         340.43
_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 0.0033 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5987(5)
_cell_length_b                   15.0870(9)
_cell_length_c                   11.7651(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.039(2)
_cell_angle_gamma                90
_cell_volume                     1672.25(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            50871
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         2.549
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2564
_reflns_number_total             3404
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         1.426
_refine_diff_density_min         -1.122
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3404
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0878
_refine_ls_restrained_S_all      1.041
_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)+(0.1343P)²+4.5551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2208
_refine_ls_wR_factor_ref         0.2716
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C21-H21
 0.92 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.84893(14) -0.07677(8) 0.48015(10) 0.0556(4) Uani 1 1 d . . . . .
N1 N 0.7384(4) -0.0200(3) 0.3876(3) 0.0499(9) Uani 1 1 d . . . . .
N2 N 0.8264(4) -0.0321(2) 0.6001(3) 0.0425(8) Uani 1 1 d . . . . .
C1 C 0.1766(5) 0.1841(3) -0.0627(4) 0.0436(9) Uani 1 1 d . . . . .
H1 H 0.084(6) 0.208(4) -0.092(4) 0.056(14) Uiso 1 1 d . . . . .
C2 C 0.2536(4) 0.1540(3) -0.1420(3) 0.0383(9) Uani 1 1 d . . . . .
H2 H 0.222(5) 0.157(3) -0.218(4) 0.039(11) Uiso 1 1 d . . . . .
C3 C 0.3864(4) 0.1186(3) -0.1051(3) 0.0391(8) Uani 1 1 d . . . . .
H3 H 0.4397 0.0977 -0.1598 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4424(4) 0.1136(3) 0.0129(4) 0.0415(9) Uani 1 1 d . . . . .
H4 H 0.538(5) 0.092(3) 0.039(4) 0.047(12) Uiso 1 1 d . . . . .
C5 C 0.3635(5) 0.1434(3) 0.0952(3) 0.0416(9) Uani 1 1 d . . . . .
C6 C 0.2306(5) 0.1780(3) 0.0542(4) 0.0436(9) Uani 1 1 d . . . . .
H6 H 0.167(6) 0.194(4) 0.110(5) 0.072(16) Uiso 1 1 d . . . . .
C7 C 0.4080(5) 0.1404(3) 0.2218(4) 0.0465(10) Uani 1 1 d . . . . .
H7 H 0.3483 0.1681 0.2670 0.056 Uiso 1 1 calc R U . . .
C8 C 0.5253(5) 0.1021(3) 0.2771(4) 0.0487(10) Uani 1 1 d . . . . .
H8 H 0.590(4) 0.073(3) 0.223(3) 0.027(9) Uiso 1 1 d . . . . .
C9 C 0.5676(5) 0.0985(3) 0.4049(3) 0.0448(10) Uani 1 1 d . . . . .
C10 C 0.6741(5) 0.0372(3) 0.4506(3) 0.0434(10) Uani 1 1 d . . . . .
C11 C 0.7259(4) 0.0305(2) 0.5730(3) 0.0356(8) Uani 1 1 d . . . . .
C12 C 0.6737(4) 0.0860(2) 0.6542(3) 0.0326(8) Uani 1 1 d . . . . .
C13 C 0.7386(4) 0.0805(2) 0.7769(3) 0.0327(8) Uani 1 1 d . . . . .
H13 H 0.790(5) 0.023(3) 0.802(4) 0.051(13) Uiso 1 1 d . . . . .
C14 C 0.7442(4) 0.1485(3) 0.8513(3) 0.0358(8) Uani 1 1 d . . . . .
H14 H 0.702(6) 0.212(4) 0.821(4) 0.064(15) Uiso 1 1 d . . . . .
C15 C 0.8088(4) 0.1478(2) 0.9740(3) 0.0334(8) Uani 1 1 d . . . . .
C16 C 0.8449(4) 0.0697(3) 1.0376(3) 0.0397(9) Uani 1 1 d . . . . .
H16 H 0.825(5) 0.011(3) 1.001(4) 0.046(12) Uiso 1 1 d . . . . .
C17 C 0.9051(5) 0.0728(3) 1.1533(4) 0.0463(10) Uani 1 1 d . . . . .
H17 H 0.929(5) 0.015(3) 1.196(4) 0.044(12) Uiso 1 1 d . . . . .
C18 C 0.9316(5) 0.1528(3) 1.2094(4) 0.0509(11) Uani 1 1 d . . . . .
H18 H 0.977(6) 0.150(3) 1.290(5) 0.061(15) Uiso 1 1 d . . . . .
C19 C 0.8983(5) 0.2308(3) 1.1486(4) 0.0467(10) Uani 1 1 d . . . . .
H19 H 0.917(5) 0.289(3) 1.181(4) 0.053(13) Uiso 1 1 d . . . . .
C20 C 0.8367(4) 0.2290(3) 1.0318(3) 0.0389(9) Uani 1 1 d . . . . .
H20 H 0.811(5) 0.287(3) 0.987(4) 0.045(12) Uiso 1 1 d . . . . .
C21 C 0.5641(4) 0.1449(2) 0.6071(3) 0.0373(9) Uani 1 1 d D . . . .
H21 H 0.523(4) 0.180(2) 0.654(3) 0.031(10) Uiso 1 1 d D . . . .
C22 C 0.5155(5) 0.1488(3) 0.4844(4) 0.0411(9) Uani 1 1 d . . . . .
H22 H 0.447(5) 0.192(4) 0.464(4) 0.055(14) Uiso 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 N1 1.613(4) . ?
S1 N2 1.615(3) . ?
N1 C10 1.360(6) . ?
N2 C11 1.345(5) . ?
C1 H1 0.96(5) . ?
C1 C2 1.373(6) . ?
C1 C6 1.377(6) . ?
C2 H2 0.89(4) . ?
C2 C3 1.374(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(5) . ?
C4 H4 0.97(5) . ?
C4 C5 1.412(6) . ?
C5 C6 1.376(6) . ?
C5 C7 1.470(5) . ?
C6 H6 1.00(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.321(6) . ?
C8 H8 1.06(4) . ?
C8 C9 1.482(6) . ?
C9 C10 1.407(6) . ?
C9 C22 1.371(6) . ?
C10 C11 1.433(5) . ?
C11 C12 1.431(5) . ?
C12 C13 1.461(5) . ?
C12 C21 1.408(5) . ?
C13 H13 1.01(5) . ?
C13 C14 1.342(5) . ?
C14 H14 1.07(6) . ?
C14 C15 1.457(5) . ?
C15 C16 1.404(5) . ?
C15 C20 1.402(5) . ?
C16 H16 0.98(5) . ?
C16 C17 1.374(6) . ?
C17 H17 1.01(5) . ?
C17 C18 1.376(7) . ?
C18 H18 0.97(5) . ?
C18 C19 1.382(7) . ?
C19 H19 0.96(5) . ?
C19 C20 1.389(5) . ?
C20 H20 1.03(5) . ?
C21 H21 0.913(10) . ?
C21 C22 1.430(5) . ?
C22 H22 0.92(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 S1 N2 100.80(19) . . ?
C10 N1 S1 106.1(3) . . ?
C11 N2 S1 107.2(3) . . ?
C2 C1 H1 117(3) . . ?
C2 C1 C6 120.5(4) . . ?
C6 C1 H1 122(3) . . ?
C1 C2 H2 123(3) . . ?
C1 C2 C3 120.1(4) . . ?
C3 C2 H2 117(3) . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120(3) . . ?
C3 C4 C5 120.8(4) . . ?
C5 C4 H4 119(3) . . ?
C4 C5 C7 126.5(4) . . ?
C6 C5 C4 117.6(3) . . ?
C6 C5 C7 115.9(4) . . ?
C1 C6 H6 118(3) . . ?
C5 C6 C1 121.5(4) . . ?
C5 C6 H6 120(3) . . ?
C5 C7 H7 117.7 . . ?
C8 C7 C5 124.6(4) . . ?
C8 C7 H7 117.7 . . ?
C7 C8 H8 115(2) . . ?
C7 C8 C9 123.9(5) . . ?
C9 C8 H8 121(2) . . ?
C10 C9 C8 116.7(4) . . ?
C22 C9 C8 127.4(4) . . ?
C22 C9 C10 115.9(4) . . ?
N1 C10 C9 125.5(4) . . ?
N1 C10 C11 113.4(4) . . ?
C9 C10 C11 121.1(4) . . ?
N2 C11 C10 112.5(4) . . ?
N2 C11 C12 125.4(3) . . ?
C12 C11 C10 122.1(4) . . ?
C11 C12 C13 119.3(3) . . ?
C21 C12 C11 115.9(3) . . ?
C21 C12 C13 124.8(3) . . ?
C12 C13 H13 115(3) . . ?
C14 C13 C12 123.9(3) . . ?
C14 C13 H13 120(3) . . ?
C13 C14 H14 120(3) . . ?
C13 C14 C15 126.6(4) . . ?
C15 C14 H14 114(3) . . ?
C16 C15 C14 123.2(3) . . ?
C20 C15 C14 118.7(3) . . ?
C20 C15 C16 118.1(3) . . ?
C15 C16 H16 121(3) . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16 118(3) . . ?
C16 C17 H17 118(3) . . ?
C16 C17 C18 120.7(4) . . ?
C18 C17 H17 121(2) . . ?
C17 C18 H18 116(3) . . ?
C17 C18 C19 119.7(4) . . ?
C19 C18 H18 124(3) . . ?
C18 C19 H19 125(3) . . ?
C18 C19 C20 120.5(4) . . ?
C20 C19 H19 115(3) . . ?
C15 C20 H20 119(2) . . ?
C19 C20 C15 120.2(4) . . ?
C19 C20 H20 121(3) . . ?
C12 C21 H21 121(2) . . ?
C12 C21 C22 119.9(4) . . ?
C22 C21 H21 119(2) . . ?
C9 C22 C21 125.1(4) . . ?
C9 C22 H22 123(3) . . ?
C21 C22 H22 112(3) . . ?

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 C10 C9 -178.7(3) . . . . ?
S1 N1 C10 C11 1.5(4) . . . . ?
S1 N2 C11 C10 -0.3(4) . . . . ?
S1 N2 C11 C12 179.9(3) . . . . ?
N1 S1 N2 C11 1.2(3) . . . . ?
N1 C10 C11 N2 -0.8(5) . . . . ?
N1 C10 C11 C12 179.0(3) . . . . ?
N2 S1 N1 C10 -1.6(3) . . . . ?
N2 C11 C12 C13 4.5(6) . . . . ?
N2 C11 C12 C21 -177.6(4) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C2 C1 C6 C5 1.2(6) . . . . ?
C2 C3 C4 C5 0.9(6) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C3 C4 C5 C7 178.7(4) . . . . ?
C4 C5 C6 C1 -0.5(6) . . . . ?
C4 C5 C7 C8 -6.1(7) . . . . ?
C5 C7 C8 C9 -179.0(4) . . . . ?
C6 C1 C2 C3 -0.9(6) . . . . ?
C6 C5 C7 C8 173.2(4) . . . . ?
C7 C5 C6 C1 -179.9(4) . . . . ?
C7 C8 C9 C10 164.4(4) . . . . ?
C7 C8 C9 C22 -16.2(7) . . . . ?
C8 C9 C10 N1 -1.8(6) . . . . ?
C8 C9 C10 C11 177.9(3) . . . . ?
C8 C9 C22 C21 -177.4(4) . . . . ?
C9 C10 C11 N2 179.5(4) . . . . ?
C9 C10 C11 C12 -0.7(6) . . . . ?
C10 C9 C22 C21 1.9(6) . . . . ?
C10 C11 C12 C13 -175.3(3) . . . . ?
C10 C11 C12 C21 2.6(5) . . . . ?
C11 C12 C13 C14 151.1(4) . . . . ?
C11 C12 C21 C22 -2.2(5) . . . . ?
C12 C13 C14 C15 -179.1(3) . . . . ?
C12 C21 C22 C9 0.0(6) . . . . ?
C13 C12 C21 C22 175.6(3) . . . . ?
C13 C14 C15 C16 -15.8(6) . . . . ?
C13 C14 C15 C20 164.2(4) . . . . ?
C14 C15 C16 C17 -179.7(4) . . . . ?
C14 C15 C20 C19 -180.0(4) . . . . ?
C15 C16 C17 C18 0.0(7) . . . . ?
C16 C15 C20 C19 0.0(6) . . . . ?
C16 C17 C18 C19 -0.6(7) . . . . ?
C17 C18 C19 C20 0.9(7) . . . . ?
C18 C19 C20 C15 -0.6(6) . . . . ?
C20 C15 C16 C17 0.3(6) . . . . ?
C21 C12 C13 C14 -26.6(6) . . . . ?
C22 C9 C10 N1 178.8(4) . . . . ?
C22 C9 C10 C11 -1.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
