# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_e21sel5
_database_code_depnum_ccdc_archive 'CCDC 2382855'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2024-09-09 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 N O2 S2, F6 P, C H2 Cl2'
_chemical_formula_sum            'C24 H22 Cl2 F6 N O2 P S2'
_chemical_formula_weight         636.41

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'
O O 0.0106 0.0060 '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'
P P 0.1023 0.0942 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.8190(4)
_cell_length_b                   15.0239(6)
_cell_length_c                   18.3666(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.389(4)
_cell_angle_gamma                90
_cell_volume                     2697.46(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5317
_cell_measurement_theta_min      3.5380
_cell_measurement_theta_max      25.3020

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.521
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_T_min  0.93951
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.905
_oxdiff_exptl_absorpt_empirical_full_max 1.162
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.0(3)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.0734
_diffrn_reflns_number            20048
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.205
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4931
_reflns_number_gt                3830
_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       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    
; 
 SHELXT
 Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_computing_structure_refinement  
;
 SHELXL-2018/3 (Sheldrick, 2018)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_refine_special_details          
;
 The solevnt molecule of CH2Cl2 is partially disordered in the ratio 63:37.
 Potential disorder in PF6 but solving it leads to over refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0341P)²+3.9368P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4931
_refine_ls_number_parameters     372
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.041
_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
S1 S 0.74877(8) 0.38067(5) 0.49663(4) 0.02476(19) Uani 1 1 d . . . . .
O1 O 0.8186(2) 0.40381(15) 0.56511(12) 0.0359(6) Uani 1 1 d . . . . .
O2 O 0.7785(2) 0.42274(13) 0.43062(11) 0.0285(5) Uani 1 1 d . . . . .
S2 S 0.71232(8) 0.27189(5) 0.33752(4) 0.02209(19) Uani 1 1 d . . . . .
N N 0.7906(2) 0.27237(16) 0.48445(13) 0.0237(6) Uani 1 1 d . . . . .
C1 C 0.5725(3) 0.37871(19) 0.50335(16) 0.0223(7) Uani 1 1 d . . . . .
C2 C 0.4845(3) 0.39572(19) 0.44150(17) 0.0252(7) Uani 1 1 d . . . . .
H2 H 0.518936 0.410030 0.396297 0.030 Uiso 1 1 calc R U . . .
C3 C 0.3450(3) 0.3913(2) 0.44727(18) 0.0294(7) Uani 1 1 d . . . . .
H3 H 0.283318 0.402877 0.405318 0.035 Uiso 1 1 calc R U . . .
C4 C 0.2935(3) 0.3705(2) 0.51257(19) 0.0322(8) Uani 1 1 d . . . . .
C5 C 0.1416(3) 0.3656(2) 0.5183(2) 0.0442(10) Uani 1 1 d . . . . .
H5A H 0.092607 0.380197 0.470836 0.066 Uiso 1 1 calc R U . . .
H5B H 0.116289 0.408237 0.555134 0.066 Uiso 1 1 calc R U . . .
H5C H 0.117096 0.305335 0.532664 0.066 Uiso 1 1 calc R U . . .
C6 C 0.3855(4) 0.3555(2) 0.57369(19) 0.0361(8) Uani 1 1 d . . . . .
H6 H 0.351452 0.342336 0.619206 0.043 Uiso 1 1 calc R U . . .
C7 C 0.5243(3) 0.3594(2) 0.56978(18) 0.0321(8) Uani 1 1 d . . . . .
H7 H 0.585977 0.348889 0.611931 0.038 Uiso 1 1 calc R U . . .
C8 C 0.8378(3) 0.2153(2) 0.54009(17) 0.0310(8) Uani 1 1 d . . . . .
H8 H 0.854108 0.230648 0.590322 0.037 Uiso 1 1 calc R U . . .
C9 C 0.8569(4) 0.1340(2) 0.51136(18) 0.0351(8) Uani 1 1 d . . . . .
H9 H 0.889802 0.082709 0.537718 0.042 Uiso 1 1 calc R U . . .
C10 C 0.8195(4) 0.1384(2) 0.43540(19) 0.0343(8) Uani 1 1 d . . . . .
H10 H 0.822021 0.090908 0.401439 0.041 Uiso 1 1 calc R U . . .
C11 C 0.7790(3) 0.2236(2) 0.41982(16) 0.0240(7) Uani 1 1 d . . . . .
C12 C 0.8568(3) 0.29393(19) 0.28770(17) 0.0256(7) Uani 1 1 d . . . . .
C13 C 0.9879(3) 0.2744(2) 0.3155(2) 0.0388(9) Uani 1 1 d . . . . .
H13 H 1.006114 0.246995 0.361990 0.047 Uiso 1 1 calc R U . . .
C14 C 1.0932(4) 0.2960(3) 0.2731(3) 0.0536(11) Uani 1 1 d . . . . .
H14 H 1.185204 0.283576 0.290924 0.064 Uiso 1 1 calc R U . . .
C15 C 1.0656(5) 0.3349(3) 0.2060(3) 0.0558(13) Uani 1 1 d . . . . .
H15 H 1.138511 0.348868 0.177432 0.067 Uiso 1 1 calc R U . . .
C16 C 0.9339(5) 0.3539(3) 0.1797(2) 0.0529(11) Uani 1 1 d . . . . .
H16 H 0.916008 0.380814 0.132976 0.063 Uiso 1 1 calc R U . . .
C17 C 0.8268(4) 0.3342(2) 0.22040(18) 0.0368(8) Uani 1 1 d . . . . .
H17 H 0.735191 0.347864 0.202755 0.044 Uiso 1 1 calc R U . . .
C18 C 0.6286(3) 0.18191(19) 0.28878(16) 0.0231(7) Uani 1 1 d . . . . .
C19 C 0.6994(3) 0.1176(2) 0.25410(17) 0.0280(7) Uani 1 1 d . . . . .
H19 H 0.796505 0.118459 0.256470 0.034 Uiso 1 1 calc R U . . .
C20 C 0.6243(4) 0.0519(2) 0.21571(18) 0.0355(8) Uani 1 1 d . . . . .
H20 H 0.669995 0.006961 0.190978 0.043 Uiso 1 1 calc R U . . .
C21 C 0.4838(4) 0.0514(2) 0.21320(19) 0.0408(9) Uani 1 1 d . . . . .
H21 H 0.433625 0.005541 0.187074 0.049 Uiso 1 1 calc R U . . .
C22 C 0.4146(4) 0.1163(2) 0.2480(2) 0.0405(9) Uani 1 1 d . . . . .
H22 H 0.317581 0.115268 0.245752 0.049 Uiso 1 1 calc R U . . .
C23 C 0.4877(3) 0.1829(2) 0.28616(18) 0.0324(8) Uani 1 1 d . . . . .
H23 H 0.441776 0.228438 0.310119 0.039 Uiso 1 1 calc R U . . .
P P 0.44382(9) 0.46895(6) 0.21966(5) 0.0284(2) Uani 1 1 d . . . . .
F1 F 0.5753(2) 0.46386(16) 0.27718(11) 0.0557(6) Uani 1 1 d . . . . .
F2 F 0.3129(2) 0.47324(15) 0.16236(11) 0.0516(6) Uani 1 1 d . . . . .
F3 F 0.4456(3) 0.36510(15) 0.21160(18) 0.0878(9) Uani 1 1 d . . . . .
F4 F 0.3458(2) 0.4607(2) 0.28304(12) 0.0775(9) Uani 1 1 d . . . . .
F5 F 0.4420(3) 0.57337(15) 0.22779(17) 0.0819(9) Uani 1 1 d . . . . .
F6 F 0.5410(2) 0.47827(17) 0.15645(12) 0.0604(7) Uani 1 1 d . . . . .
C24 C 0.6630(8) 0.9204(8) 0.5505(4) 0.051(3) Uani 0.632(17) 1 d . U P A 1
H24A H 0.653733 0.984819 0.539657 0.062 Uiso 0.632(17) 1 calc R U P A 1
H24B H 0.678965 0.913537 0.604270 0.062 Uiso 0.632(17) 1 calc R U P A 1
Cl1 Cl 0.8029(7) 0.8789(6) 0.5105(6) 0.092(2) Uani 0.632(17) 1 d . U P A 1
Cl2 Cl 0.5115(3) 0.8667(2) 0.51953(17) 0.0474(12) Uani 0.632(17) 1 d . U P A 1
C24A C 0.697(2) 0.8648(19) 0.5552(9) 0.079(6) Uani 0.368(17) 1 d . U P A 2
H24C H 0.722024 0.904426 0.597449 0.095 Uiso 0.368(17) 1 calc R U P A 2
H24D H 0.715643 0.802533 0.570631 0.095 Uiso 0.368(17) 1 calc R U P A 2
Cl1A Cl 0.7909(11) 0.8924(9) 0.4826(8) 0.078(3) Uani 0.368(17) 1 d . U P A 2
Cl2A Cl 0.5179(13) 0.8785(11) 0.5233(7) 0.154(5) Uani 0.368(17) 1 d . U P A 2


_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 1.418(2) . ?
S1 O2 1.422(2) . ?
S1 N 1.698(2) . ?
S1 C1 1.747(3) . ?
S2 C11 1.747(3) . ?
S2 C18 1.779(3) . ?
S2 C12 1.790(3) . ?
N C8 1.380(4) . ?
N C11 1.390(4) . ?
C1 C7 1.380(4) . ?
C1 C2 1.385(4) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C6 1.392(5) . ?
C4 C5 1.507(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.373(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.351(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.410(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.363(4) . ?
C10 H10 0.9500 . ?
C12 C13 1.372(5) . ?
C12 C17 1.383(5) . ?
C13 C14 1.389(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.369(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.367(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.380(4) . ?
C18 C19 1.380(4) . ?
C19 C20 1.385(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
P F3 1.567(2) . ?
P F5 1.576(2) . ?
P F6 1.577(2) . ?
P F4 1.584(2) . ?
P F2 1.584(2) . ?
P F1 1.591(2) . ?
C24 Cl1 1.735(10) . ?
C24 Cl2 1.741(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24A Cl1A 1.742(19) . ?
C24A Cl2A 1.81(2) . ?
C24A H24C 0.9900 . ?
C24A H24D 0.9900 . ?

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 O2 121.77(14) . . ?
O1 S1 N 104.41(13) . . ?
O2 S1 N 104.00(12) . . ?
O1 S1 C1 109.96(14) . . ?
O2 S1 C1 110.60(14) . . ?
N S1 C1 104.29(13) . . ?
C11 S2 C18 103.76(14) . . ?
C11 S2 C12 105.57(15) . . ?
C18 S2 C12 103.55(14) . . ?
C8 N C11 107.5(2) . . ?
C8 N S1 124.5(2) . . ?
C11 N S1 128.0(2) . . ?
C7 C1 C2 121.6(3) . . ?
C7 C1 S1 119.3(2) . . ?
C2 C1 S1 119.0(2) . . ?
C1 C2 C3 118.3(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C6 118.3(3) . . ?
C3 C4 C5 121.2(3) . . ?
C6 C4 C5 120.5(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 121.6(3) . . ?
C7 C6 H6 119.2 . . ?
C4 C6 H6 119.2 . . ?
C6 C7 C1 118.6(3) . . ?
C6 C7 H7 120.7 . . ?
C1 C7 H7 120.7 . . ?
C9 C8 N 108.8(3) . . ?
C9 C8 H8 125.6 . . ?
N C8 H8 125.6 . . ?
C8 C9 C10 108.1(3) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
C11 C10 C9 107.2(3) . . ?
C11 C10 H10 126.4 . . ?
C9 C10 H10 126.4 . . ?
C10 C11 N 108.4(3) . . ?
C10 C11 S2 130.5(3) . . ?
N C11 S2 121.0(2) . . ?
C13 C12 C17 122.6(3) . . ?
C13 C12 S2 122.1(3) . . ?
C17 C12 S2 115.2(3) . . ?
C12 C13 C14 117.6(4) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 H13 121.2 . . ?
C15 C14 C13 120.6(4) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.5(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 118.0(4) . . ?
C16 C17 H17 121.0 . . ?
C12 C17 H17 121.0 . . ?
C23 C18 C19 122.6(3) . . ?
C23 C18 S2 115.1(2) . . ?
C19 C18 S2 122.3(2) . . ?
C18 C19 C20 117.8(3) . . ?
C18 C19 H19 121.1 . . ?
C20 C19 H19 121.1 . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 121.1(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C23 119.5(3) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C18 C23 C22 118.7(3) . . ?
C18 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
F3 P F5 180.0(2) . . ?
F3 P F6 90.34(16) . . ?
F5 P F6 89.68(15) . . ?
F3 P F4 90.25(17) . . ?
F5 P F4 89.73(17) . . ?
F6 P F4 179.38(16) . . ?
F3 P F2 89.62(14) . . ?
F5 P F2 90.39(14) . . ?
F6 P F2 90.95(12) . . ?
F4 P F2 88.87(12) . . ?
F3 P F1 89.97(15) . . ?
F5 P F1 90.03(14) . . ?
F6 P F1 89.08(12) . . ?
F4 P F1 91.11(12) . . ?
F2 P F1 179.58(14) . . ?
Cl1 C24 Cl2 112.4(5) . . ?
Cl1 C24 H24A 109.1 . . ?
Cl2 C24 H24A 109.1 . . ?
Cl1 C24 H24B 109.1 . . ?
Cl2 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
Cl1A C24A Cl2A 107.0(14) . . ?
Cl1A C24A H24C 110.3 . . ?
Cl2A C24A H24C 110.3 . . ?
Cl1A C24A H24D 110.3 . . ?
Cl2A C24A H24D 110.3 . . ?
H24C C24A H24D 108.6 . . ?

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
O1 S1 N C8 20.9(3) . . . . ?
O2 S1 N C8 149.5(2) . . . . ?
C1 S1 N C8 -94.5(3) . . . . ?
O1 S1 N C11 -162.4(2) . . . . ?
O2 S1 N C11 -33.7(3) . . . . ?
C1 S1 N C11 82.2(3) . . . . ?
O1 S1 C1 C7 -28.2(3) . . . . ?
O2 S1 C1 C7 -165.5(2) . . . . ?
N S1 C1 C7 83.3(3) . . . . ?
O1 S1 C1 C2 152.5(2) . . . . ?
O2 S1 C1 C2 15.2(3) . . . . ?
N S1 C1 C2 -96.0(2) . . . . ?
C7 C1 C2 C3 -1.2(4) . . . . ?
S1 C1 C2 C3 178.1(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C6 1.2(5) . . . . ?
C2 C3 C4 C5 -179.8(3) . . . . ?
C3 C4 C6 C7 -1.3(5) . . . . ?
C5 C4 C6 C7 179.8(3) . . . . ?
C4 C6 C7 C1 0.1(5) . . . . ?
C2 C1 C7 C6 1.1(5) . . . . ?
S1 C1 C7 C6 -178.1(2) . . . . ?
C11 N C8 C9 0.8(4) . . . . ?
S1 N C8 C9 178.1(2) . . . . ?
N C8 C9 C10 -0.8(4) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C9 C10 C11 N 0.1(4) . . . . ?
C9 C10 C11 S2 -176.3(3) . . . . ?
C8 N C11 C10 -0.6(3) . . . . ?
S1 N C11 C10 -177.8(2) . . . . ?
C8 N C11 S2 176.2(2) . . . . ?
S1 N C11 S2 -1.0(4) . . . . ?
C18 S2 C11 C10 28.2(3) . . . . ?
C12 S2 C11 C10 -80.3(3) . . . . ?
C18 S2 C11 N -147.7(2) . . . . ?
C12 S2 C11 N 103.7(2) . . . . ?
C11 S2 C12 C13 -0.6(3) . . . . ?
C18 S2 C12 C13 -109.3(3) . . . . ?
C11 S2 C12 C17 -178.9(2) . . . . ?
C18 S2 C12 C17 72.4(3) . . . . ?
C17 C12 C13 C14 -0.4(5) . . . . ?
S2 C12 C13 C14 -178.6(3) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C13 C14 C15 C16 0.5(6) . . . . ?
C14 C15 C16 C17 0.1(6) . . . . ?
C15 C16 C17 C12 -0.8(5) . . . . ?
C13 C12 C17 C16 1.0(5) . . . . ?
S2 C12 C17 C16 179.3(3) . . . . ?
C11 S2 C18 C23 104.9(2) . . . . ?
C12 S2 C18 C23 -145.0(2) . . . . ?
C11 S2 C18 C19 -77.2(3) . . . . ?
C12 S2 C18 C19 32.9(3) . . . . ?
C23 C18 C19 C20 -0.3(5) . . . . ?
S2 C18 C19 C20 -178.0(2) . . . . ?
C18 C19 C20 C21 -0.4(5) . . . . ?
C19 C20 C21 C22 0.6(5) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
C19 C18 C23 C22 0.8(5) . . . . ?
S2 C18 C23 C22 178.6(2) . . . . ?
C21 C22 C23 C18 -0.5(5) . . . . ?

_refine_diff_density_max         0.633
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.062



####################################################################### 
# 
# 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_s24sel4
_database_code_depnum_ccdc_archive 'CCDC 2382856'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2024-09-09 deposited with the CCDC.	2024-10-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H29 N O2 S2'
_chemical_formula_sum            'C23 H29 N O2 S2'
_chemical_formula_weight         415.59

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.62050(10)
_cell_length_b                   21.84591(17)
_cell_length_c                   9.44371(17)
_cell_angle_alpha                90
_cell_angle_beta                 111.2805(12)
_cell_angle_gamma                90
_cell_volume                     2233.92(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    23096
_cell_measurement_theta_min      4.5420
_cell_measurement_theta_max      72.8060

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.405
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.126
_exptl_absorpt_coefficient_mu    2.293
_shelx_estimated_absorpt_T_min   0.457
_shelx_estimated_absorpt_T_max   0.761
_exptl_absorpt_correction_T_min  0.60639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.713
_oxdiff_exptl_absorpt_empirical_full_max 1.362
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            43002
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.047
_diffrn_reflns_theta_max         72.941
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4465
_reflns_number_gt                4252
_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       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  
;
 SHELXL-2019/2 (Sheldrick, 2019)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_refine_special_details          
;
the thiophene ligand shows inversion disorder in the ratio 61:39
all non S disordered atoms have been refined with ADP restraints.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+0.8410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4465
_refine_ls_number_parameters     305
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.068
_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
O1 O 0.80963(11) 0.33494(6) 0.54438(16) 0.0560(4) Uani 1 1 d . . . . .
O2 O 0.77369(11) 0.28923(5) 0.76080(15) 0.0503(3) Uani 1 1 d . . . . .
S1 S 0.74127(3) 0.33436(2) 0.64288(4) 0.03874(12) Uani 1 1 d . . . . .
C1 C 0.73572(11) 0.40822(6) 0.71815(15) 0.0283(3) Uani 1 1 d . . . . .
C2 C 0.73721(11) 0.41480(6) 0.86765(15) 0.0278(3) Uani 1 1 d . . . . .
C3 C 0.71460(14) 0.36458(7) 0.96666(18) 0.0391(3) Uani 1 1 d . . . . .
H3 H 0.685917 0.327303 0.901922 0.047 Uiso 1 1 calc R U . . .
C4 C 0.8337(2) 0.34804(9) 1.0971(2) 0.0637(6) Uani 1 1 d . . . . .
H4A H 0.816711 0.316080 1.159675 0.096 Uiso 1 1 calc R U . . .
H4B H 0.866313 0.384411 1.159552 0.096 Uiso 1 1 calc R U . . .
H4C H 0.894639 0.333009 1.055915 0.096 Uiso 1 1 calc R U . . .
C5 C 0.61263(19) 0.38304(9) 1.0248(2) 0.0572(5) Uani 1 1 d . . . . .
H5A H 0.593026 0.348336 1.077843 0.086 Uiso 1 1 calc R U . . .
H5B H 0.538650 0.395005 0.938780 0.086 Uiso 1 1 calc R U . . .
H5C H 0.640886 0.417621 1.095066 0.086 Uiso 1 1 calc R U . . .
C6 C 0.75729(12) 0.47336(6) 0.92913(14) 0.0289(3) Uani 1 1 d . . . . .
H6 H 0.760221 0.478786 1.030195 0.035 Uiso 1 1 calc R U . . .
C7 C 0.77327(12) 0.52429(6) 0.85060(15) 0.0287(3) Uani 1 1 d . . . . .
C8 C 0.79973(14) 0.58670(7) 0.92537(18) 0.0374(3) Uani 1 1 d . . . . .
H8 H 0.810878 0.616387 0.850770 0.045 Uiso 1 1 calc R U . . .
C9 C 0.69166(17) 0.60846(8) 0.9676(2) 0.0545(5) Uani 1 1 d . . . . .
H9A H 0.707644 0.650243 1.007803 0.082 Uiso 1 1 calc R U . . .
H9B H 0.682080 0.581229 1.045064 0.082 Uiso 1 1 calc R U . . .
H9C H 0.615819 0.607903 0.877136 0.082 Uiso 1 1 calc R U . . .
C10 C 0.91857(17) 0.58613(8) 1.0665(2) 0.0561(5) Uani 1 1 d . . . . .
H10A H 0.937264 0.627791 1.106810 0.084 Uiso 1 1 calc R U . . .
H10B H 0.986916 0.570832 1.038901 0.084 Uiso 1 1 calc R U . . .
H10C H 0.907544 0.559420 1.143944 0.084 Uiso 1 1 calc R U . . .
C11 C 0.75946(12) 0.51653(7) 0.69960(15) 0.0316(3) Uani 1 1 d . . . . .
H11 H 0.764377 0.551492 0.642255 0.038 Uiso 1 1 calc R U . . .
C12 C 0.73870(11) 0.45961(7) 0.62861(15) 0.0307(3) Uani 1 1 d . . . . .
C13 C 0.71603(14) 0.45806(9) 0.45837(16) 0.0409(4) Uani 1 1 d . . . . .
H13 H 0.695669 0.415054 0.421546 0.049 Uiso 1 1 calc R U . . .
C14 C 0.60570(16) 0.49903(10) 0.37088(18) 0.0534(5) Uani 1 1 d . . . . .
H14A H 0.593323 0.498576 0.262563 0.080 Uiso 1 1 calc R U . . .
H14B H 0.622114 0.541010 0.409553 0.080 Uiso 1 1 calc R U . . .
H14C H 0.531263 0.483631 0.384708 0.080 Uiso 1 1 calc R U . . .
C15 C 0.83330(16) 0.47750(10) 0.43129(19) 0.0538(5) Uani 1 1 d . . . . .
H15A H 0.817874 0.476341 0.322180 0.081 Uiso 1 1 calc R U . . .
H15B H 0.900809 0.449394 0.484869 0.081 Uiso 1 1 calc R U . . .
H15C H 0.856098 0.519188 0.469526 0.081 Uiso 1 1 calc R U . . .
C16 C 0.55465(16) 0.29417(7) 0.39043(18) 0.0424(4) Uani 1 1 d . . . . .
H16 H 0.604116 0.283331 0.333311 0.051 Uiso 1 1 calc R U . . .
C17 C 0.43107(17) 0.28470(8) 0.3499(2) 0.0512(4) Uani 1 1 d . . . . .
H17 H 0.379038 0.266043 0.258141 0.061 Uiso 1 1 calc R U . . .
C18 C 0.39220(14) 0.30710(6) 0.46640(18) 0.0389(3) Uani 1 1 d D . . . .
C19 C 0.49484(14) 0.32949(9) 0.5763(2) 0.0504(4) Uani 1 1 d . . . . .
H19 H 0.497951 0.347091 0.669621 0.060 Uiso 1 1 calc R U . . .
N N 0.59410(11) 0.32247(6) 0.53012(16) 0.0428(3) Uani 1 1 d . . . . .
S2 S 0.2288(2) 0.34275(12) 0.5899(3) 0.0635(9) Uani 0.618(3) 1 d D . P A 1
C20 C 0.2676(7) 0.3039(5) 0.4572(11) 0.049(2) Uani 0.618(3) 1 d D U P A 1
C21 C 0.0800(4) 0.3190(3) 0.5146(8) 0.0631(19) Uani 0.618(3) 1 d D U P A 1
H21 H 0.016673 0.331353 0.549906 0.076 Uiso 0.618(3) 1 calc R U P A 1
C22 C 0.0636(4) 0.2801(2) 0.3976(7) 0.0680(14) Uani 0.618(3) 1 d D U P A 1
H22 H -0.013963 0.261195 0.345433 0.082 Uiso 0.618(3) 1 calc R U P A 1
C23 C 0.1710(7) 0.2684(4) 0.3549(11) 0.062(2) Uani 0.618(3) 1 d D U P A 1
H23 H 0.174980 0.242536 0.275844 0.074 Uiso 0.618(3) 1 calc R U P A 1
S2A S 0.1390(3) 0.27556(16) 0.3606(3) 0.0435(6) Uani 0.382(3) 1 d D . P A 2
C20A C 0.2683(8) 0.3110(7) 0.4856(16) 0.0291(18) Uani 0.382(3) 1 d D U P A 2
C21A C 0.0418(6) 0.2984(3) 0.4468(7) 0.0340(12) Uani 0.382(3) 1 d D U P A 2
H21A H -0.043090 0.287659 0.414161 0.041 Uiso 0.382(3) 1 calc R U P A 2
C22A C 0.1021(8) 0.3345(4) 0.5703(9) 0.0445(17) Uani 0.382(3) 1 d D U P A 2
H22A H 0.068252 0.346598 0.643664 0.053 Uiso 0.382(3) 1 calc R U P A 2
C23A C 0.2258(9) 0.3521(5) 0.5753(12) 0.0160(13) Uani 0.382(3) 1 d D U P A 2
H23A H 0.271473 0.386045 0.630332 0.019 Uiso 0.382(3) 1 calc R U P A 2


_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
O1 S1 1.4258(13) . ?
O2 S1 1.4316(13) . ?
S1 N 1.6745(13) . ?
S1 C1 1.7738(14) . ?
C1 C2 1.4131(19) . ?
C1 C12 1.413(2) . ?
C2 C6 1.3891(19) . ?
C2 C3 1.5248(19) . ?
C3 C4 1.525(2) . ?
C3 C5 1.530(2) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.3866(18) . ?
C6 H6 0.9500 . ?
C7 C11 1.3863(19) . ?
C7 C8 1.5147(19) . ?
C8 C9 1.525(2) . ?
C8 C10 1.532(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.5323(18) . ?
C13 C15 1.535(2) . ?
C13 C14 1.536(2) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.361(3) . ?
C16 N 1.3761(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.419(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.357(2) . ?
C18 C20 1.421(7) . ?
C18 C20A 1.518(8) . ?
C19 N 1.382(2) . ?
C19 H19 0.9500 . ?
S2 C21 1.695(5) . ?
S2 C20 1.704(8) . ?
C20 C23 1.418(10) . ?
C21 C22 1.352(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.467(7) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
S2A C21A 1.690(7) . ?
S2A C20A 1.721(10) . ?
C20A C23A 1.438(11) . ?
C21A C22A 1.371(7) . ?
C21A H21A 0.9500 . ?
C22A C23A 1.472(11) . ?
C22A H22A 0.9500 . ?
C23A H23A 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 O2 117.52(8) . . ?
O1 S1 N 105.59(7) . . ?
O2 S1 N 107.92(8) . . ?
O1 S1 C1 111.30(7) . . ?
O2 S1 C1 110.63(7) . . ?
N S1 C1 102.63(6) . . ?
C2 C1 C12 121.52(12) . . ?
C2 C1 S1 120.26(10) . . ?
C12 C1 S1 118.07(10) . . ?
C6 C2 C1 116.78(12) . . ?
C6 C2 C3 116.52(12) . . ?
C1 C2 C3 126.66(13) . . ?
C2 C3 C4 110.97(13) . . ?
C2 C3 C5 111.01(13) . . ?
C4 C3 C5 111.50(16) . . ?
C2 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
C5 C3 H3 107.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C2 123.38(12) . . ?
C7 C6 H6 118.3 . . ?
C2 C6 H6 118.3 . . ?
C11 C7 C6 117.65(12) . . ?
C11 C7 C8 121.19(12) . . ?
C6 C7 C8 121.12(12) . . ?
C7 C8 C9 110.82(13) . . ?
C7 C8 C10 111.38(13) . . ?
C9 C8 C10 110.05(15) . . ?
C7 C8 H8 108.2 . . ?
C9 C8 H8 108.2 . . ?
C10 C8 H8 108.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 C12 122.69(13) . . ?
C7 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C11 C12 C1 117.33(12) . . ?
C11 C12 C13 117.32(13) . . ?
C1 C12 C13 125.31(13) . . ?
C12 C13 C15 110.11(12) . . ?
C12 C13 C14 110.10(12) . . ?
C15 C13 C14 111.56(15) . . ?
C12 C13 H13 108.3 . . ?
C15 C13 H13 108.3 . . ?
C14 C13 H13 108.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 N 106.75(15) . . ?
C17 C16 H16 126.6 . . ?
N C16 H16 126.6 . . ?
C16 C17 C18 109.26(14) . . ?
C16 C17 H17 125.4 . . ?
C18 C17 H17 125.4 . . ?
C19 C18 C17 106.17(15) . . ?
C19 C18 C20 131.1(4) . . ?
C17 C18 C20 122.7(4) . . ?
C19 C18 C20A 119.8(5) . . ?
C17 C18 C20A 134.0(5) . . ?
C18 C19 N 108.74(15) . . ?
C18 C19 H19 125.6 . . ?
N C19 H19 125.6 . . ?
C16 N C19 109.06(13) . . ?
C16 N S1 125.97(12) . . ?
C19 N S1 123.98(12) . . ?
C21 S2 C20 92.3(4) . . ?
C23 C20 C18 127.3(7) . . ?
C23 C20 S2 114.8(6) . . ?
C18 C20 S2 117.8(6) . . ?
C22 C21 S2 110.8(4) . . ?
C22 C21 H21 124.6 . . ?
S2 C21 H21 124.6 . . ?
C21 C22 C23 116.9(5) . . ?
C21 C22 H22 121.5 . . ?
C23 C22 H22 121.5 . . ?
C20 C23 C22 105.0(7) . . ?
C20 C23 H23 127.5 . . ?
C22 C23 H23 127.5 . . ?
C21A S2A C20A 96.1(4) . . ?
C23A C20A C18 130.4(9) . . ?
C23A C20A S2A 106.5(6) . . ?
C18 C20A S2A 121.5(8) . . ?
C22A C21A S2A 110.8(6) . . ?
C22A C21A H21A 124.6 . . ?
S2A C21A H21A 124.6 . . ?
C21A C22A C23A 111.6(8) . . ?
C21A C22A H22A 124.2 . . ?
C23A C22A H22A 124.2 . . ?
C20A C23A C22A 111.0(7) . . ?
C20A C23A H23A 124.5 . . ?
C22A C23A H23A 124.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 C1 C2 -145.13(11) . . . . ?
O2 S1 C1 C2 -12.55(12) . . . . ?
N S1 C1 C2 102.35(11) . . . . ?
O1 S1 C1 C12 30.46(12) . . . . ?
O2 S1 C1 C12 163.04(10) . . . . ?
N S1 C1 C12 -82.05(11) . . . . ?
C12 C1 C2 C6 -7.83(18) . . . . ?
S1 C1 C2 C6 167.61(10) . . . . ?
C12 C1 C2 C3 169.89(13) . . . . ?
S1 C1 C2 C3 -14.67(18) . . . . ?
C6 C2 C3 C4 -72.96(18) . . . . ?
C1 C2 C3 C4 109.31(17) . . . . ?
C6 C2 C3 C5 51.63(18) . . . . ?
C1 C2 C3 C5 -126.10(16) . . . . ?
C1 C2 C6 C7 1.16(19) . . . . ?
C3 C2 C6 C7 -176.80(13) . . . . ?
C2 C6 C7 C11 4.8(2) . . . . ?
C2 C6 C7 C8 -177.65(13) . . . . ?
C11 C7 C8 C9 113.93(16) . . . . ?
C6 C7 C8 C9 -63.56(18) . . . . ?
C11 C7 C8 C10 -123.19(16) . . . . ?
C6 C7 C8 C10 59.32(19) . . . . ?
C6 C7 C11 C12 -4.4(2) . . . . ?
C8 C7 C11 C12 178.07(13) . . . . ?
C7 C11 C12 C1 -1.94(19) . . . . ?
C7 C11 C12 C13 175.79(12) . . . . ?
C2 C1 C12 C11 8.23(18) . . . . ?
S1 C1 C12 C11 -167.31(10) . . . . ?
C2 C1 C12 C13 -169.30(12) . . . . ?
S1 C1 C12 C13 15.17(17) . . . . ?
C11 C12 C13 C15 66.41(18) . . . . ?
C1 C12 C13 C15 -116.07(17) . . . . ?
C11 C12 C13 C14 -57.01(18) . . . . ?
C1 C12 C13 C14 120.52(16) . . . . ?
N C16 C17 C18 -0.33(19) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C16 C17 C18 C20 179.9(6) . . . . ?
C16 C17 C18 C20A 178.3(9) . . . . ?
C17 C18 C19 N 0.9(2) . . . . ?
C20 C18 C19 N -179.3(6) . . . . ?
C20A C18 C19 N -178.0(8) . . . . ?
C17 C16 N C19 0.9(2) . . . . ?
C17 C16 N S1 169.83(13) . . . . ?
C18 C19 N C16 -1.2(2) . . . . ?
C18 C19 N S1 -170.37(12) . . . . ?
O1 S1 N C16 24.65(17) . . . . ?
O2 S1 N C16 -101.82(15) . . . . ?
C1 S1 N C16 141.32(14) . . . . ?
O1 S1 N C19 -168.02(15) . . . . ?
O2 S1 N C19 65.52(16) . . . . ?
C1 S1 N C19 -51.34(16) . . . . ?
C19 C18 C20 C23 -165.2(8) . . . . ?
C17 C18 C20 C23 14.5(14) . . . . ?
C19 C18 C20 S2 10.2(11) . . . . ?
C17 C18 C20 S2 -170.1(4) . . . . ?
C21 S2 C20 C23 -3.4(9) . . . . ?
C21 S2 C20 C18 -179.4(8) . . . . ?
C20 S2 C21 C22 3.3(6) . . . . ?
S2 C21 C22 C23 -2.6(7) . . . . ?
C18 C20 C23 C22 177.9(9) . . . . ?
S2 C20 C23 C22 2.4(11) . . . . ?
C21 C22 C23 C20 0.2(10) . . . . ?
C19 C18 C20A C23A 24.0(19) . . . . ?
C17 C18 C20A C23A -154.6(11) . . . . ?
C19 C18 C20A S2A -172.4(7) . . . . ?
C17 C18 C20A S2A 9.1(17) . . . . ?
C21A S2A C20A C23A -12.7(11) . . . . ?
C21A S2A C20A C18 -179.8(11) . . . . ?
C20A S2A C21A C22A 1.3(9) . . . . ?
S2A C21A C22A C23A 10.5(12) . . . . ?
C18 C20A C23A C22A -174.2(13) . . . . ?
S2A C20A C23A C22A 20.3(14) . . . . ?
C21A C22A C23A C20A -20.5(15) . . . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.067



