# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_5o
_database_code_depnum_ccdc_archive 'CCDC 2361608'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2024-06-10 deposited with the CCDC.	2024-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 N2 O2 S'
_chemical_formula_sum            'C16 H20 N2 O2 S'
_chemical_formula_weight         304.40

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 0.0096 '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 0.0189 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   11.5953(2)
_cell_length_b                   11.3000(2)
_cell_length_c                   24.7099(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3237.66(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      5.23
_cell_measurement_theta_max      65.04
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.822
_shelx_estimated_absorpt_T_min   0.776
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8921
_exptl_absorpt_correction_T_max  0.9526
_exptl_absorpt_process_details   'Bruker APEX4'
_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON III c7'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23306
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         5.231
_diffrn_reflns_theta_max         65.076
_diffrn_reflns_theta_full        65.077
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2731
_reflns_number_gt                2453
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0438P)²+1.2710P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2731
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
C1 C 0.65335(14) 0.75106(16) 0.68721(6) 0.0390(4) Uani 1 1 d . . . . .
C2 C 0.58380(16) 0.7042(2) 0.72772(7) 0.0519(5) Uani 1 1 d . . . . .
H2 H 0.559054 0.624171 0.725683 0.062 Uiso 1 1 calc R U . . .
C3 C 0.55051(19) 0.7742(3) 0.77111(8) 0.0710(7) Uani 1 1 d . . . . .
H3 H 0.501885 0.742114 0.798349 0.085 Uiso 1 1 calc R U . . .
C4 C 0.5870(3) 0.8890(3) 0.77505(9) 0.0841(9) Uani 1 1 d . . . . .
H4 H 0.563651 0.936523 0.804813 0.101 Uiso 1 1 calc R U . . .
C5 C 0.6567(3) 0.9347(2) 0.73632(9) 0.0834(8) Uani 1 1 d . . . . .
H5 H 0.682870 1.014053 0.739375 0.100 Uiso 1 1 calc R U . . .
C6 C 0.6902(2) 0.86688(19) 0.69225(8) 0.0587(5) Uani 1 1 d . . . . .
H6 H 0.738848 0.900264 0.665340 0.070 Uiso 1 1 calc R U . . .
C7 C 0.68197(13) 0.67756(15) 0.63896(6) 0.0329(4) Uani 1 1 d . . . . .
C8 C 0.73950(13) 0.73733(14) 0.59128(6) 0.0317(3) Uani 1 1 d . . . . .
H8A H 0.694802 0.808933 0.581639 0.038 Uiso 1 1 calc R U . . .
H8B H 0.817603 0.763263 0.602296 0.038 Uiso 1 1 calc R U . . .
C9 C 0.74994(12) 0.65961(12) 0.54168(6) 0.0263(3) Uani 1 1 d . . . . .
C10 C 0.81305(12) 0.71724(13) 0.49266(6) 0.0266(3) Uani 1 1 d . . . . .
C11 C 0.63860(11) 0.63546(12) 0.46493(6) 0.0243(3) Uani 1 1 d . . . . .
C12 C 0.84470(13) 0.56236(14) 0.54254(7) 0.0363(4) Uani 1 1 d . . . . .
H12A H 0.882614 0.553153 0.578190 0.044 Uiso 1 1 calc R U . . .
H12B H 0.818159 0.484927 0.528532 0.044 Uiso 1 1 calc R U . . .
C13 C 0.91682(13) 0.63390(14) 0.50137(7) 0.0379(4) Uani 1 1 d . . . . .
H13A H 0.984891 0.673374 0.517465 0.046 Uiso 1 1 calc R U . . .
H13B H 0.938616 0.588344 0.468713 0.046 Uiso 1 1 calc R U . . .
C14 C 0.75275(15) 0.72880(18) 0.39148(6) 0.0447(5) Uani 1 1 d . . . . .
H14 H 0.707216 0.675149 0.367409 0.054 Uiso 1 1 calc R U . . .
C15 C 0.7048(2) 0.85344(19) 0.38396(8) 0.0617(6) Uani 1 1 d . . . . .
H15A H 0.706590 0.874388 0.345488 0.093 Uiso 1 1 calc R U . . .
H15B H 0.751890 0.909752 0.404489 0.093 Uiso 1 1 calc R U . . .
H15C H 0.625081 0.856243 0.397089 0.093 Uiso 1 1 calc R U . . .
C16 C 0.87828(18) 0.7193(3) 0.37415(9) 0.0756(8) Uani 1 1 d . . . . .
H16A H 0.885739 0.743735 0.336264 0.113 Uiso 1 1 calc R U . . .
H16B H 0.904221 0.637148 0.378018 0.113 Uiso 1 1 calc R U . . .
H16C H 0.925766 0.770731 0.397004 0.113 Uiso 1 1 calc R U . . .
N1 N 0.73702(10) 0.68613(11) 0.44758(5) 0.0291(3) Uani 1 1 d . . . . .
N2 N 0.63927(10) 0.62573(11) 0.51895(5) 0.0256(3) Uani 1 1 d . . . . .
O1 O 0.65682(11) 0.57314(11) 0.63700(5) 0.0459(3) Uani 1 1 d . . . . .
O2 O 0.83077(9) 0.83910(9) 0.49132(4) 0.0297(3) Uani 1 1 d . . . . .
H200 H 0.885735 0.856828 0.511929 0.045 Uiso 1 1 calc R U . . .
S1 S 0.52850(3) 0.59108(3) 0.42465(2) 0.02731(13) Uani 1 1 d . . . . .
H20 H 0.5933(14) 0.5806(15) 0.5356(7) 0.030(4) 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
C1 C6 1.382(3) . ?
C1 C2 1.390(2) . ?
C1 C7 1.490(2) . ?
C2 C3 1.387(3) . ?
C3 C4 1.369(4) . ?
C4 C5 1.354(4) . ?
C5 C6 1.387(3) . ?
C7 O1 1.216(2) . ?
C7 C8 1.513(2) . ?
C8 C9 1.513(2) . ?
C9 N2 1.4522(18) . ?
C9 C12 1.554(2) . ?
C9 C10 1.558(2) . ?
C10 O2 1.3926(17) . ?
C10 N1 1.4634(18) . ?
C10 C13 1.543(2) . ?
C11 N2 1.3392(19) . ?
C11 N1 1.3469(18) . ?
C11 S1 1.6947(14) . ?
C12 C13 1.545(2) . ?
C14 N1 1.479(2) . ?
C14 C16 1.521(3) . ?
C14 C15 1.526(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.38(18) . . ?
C6 C1 C7 122.05(16) . . ?
C2 C1 C7 119.53(17) . . ?
C3 C2 C1 120.0(2) . . ?
C4 C3 C2 120.6(2) . . ?
C5 C4 C3 119.7(2) . . ?
C4 C5 C6 120.8(3) . . ?
C1 C6 C5 120.5(2) . . ?
O1 C7 C1 121.27(15) . . ?
O1 C7 C8 120.50(15) . . ?
C1 C7 C8 118.19(14) . . ?
C9 C8 C7 114.02(13) . . ?
N2 C9 C8 113.32(12) . . ?
N2 C9 C12 116.33(12) . . ?
C8 C9 C12 117.13(13) . . ?
N2 C9 C10 102.98(11) . . ?
C8 C9 C10 115.14(12) . . ?
C12 C9 C10 88.52(11) . . ?
O2 C10 N1 107.96(12) . . ?
O2 C10 C13 119.46(12) . . ?
N1 C10 C13 115.43(12) . . ?
O2 C10 C9 120.07(12) . . ?
N1 C10 C9 102.03(11) . . ?
C13 C10 C9 90.15(11) . . ?
N2 C11 N1 110.31(12) . . ?
N2 C11 S1 124.43(11) . . ?
N1 C11 S1 125.25(11) . . ?
C13 C12 C9 90.21(11) . . ?
C10 C13 C12 89.38(11) . . ?
N1 C14 C16 111.03(16) . . ?
N1 C14 C15 111.72(15) . . ?
C16 C14 C15 112.33(18) . . ?
C11 N1 C10 111.74(12) . . ?
C11 N1 C14 122.78(12) . . ?
C10 N1 C14 124.11(12) . . ?
C11 N2 C9 111.66(12) . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_5n
_database_code_depnum_ccdc_archive 'CCDC 2361609'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2024-06-10 deposited with the CCDC.	2024-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' 	C19 H18 N2 O2 S, C H Cl3 '
_chemical_formula_sum            'C20 H19 Cl3 N2 O2 S'
_chemical_formula_weight         457.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 '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/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                   11.0280(14)
_cell_length_b                   18.344(2)
_cell_length_c                   11.1908(13)
_cell_angle_alpha                90
_cell_angle_beta                 108.215(4)
_cell_angle_gamma                90
_cell_volume                     2150.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      29.63


_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.542
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8173
_exptl_absorpt_correction_T_max  0.9462
_exptl_absorpt_process_details   'Bruker APEX4'
_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTONIII c7'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            86872
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.214
_diffrn_reflns_theta_max         31.060
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6870
_reflns_number_gt                4277
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0657P)²+1.1406P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         6870
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1618
_refine_ls_wR_factor_gt          0.1331
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C21A C 0.9550(15) 0.2188(9) 0.9651(17) 0.057(3) Uani 0.675(3) 1 d . . P A 1
H21A H 0.998198 0.253656 1.033908 0.068 Uiso 0.675(3) 1 calc R U P A 1
Cl1A Cl 0.9142(2) 0.1470(2) 1.0348(3) 0.179(2) Uani 0.675(3) 1 d . . P A 1
Cl2A Cl 1.05573(12) 0.20525(8) 0.88364(13) 0.0743(5) Uani 0.675(3) 1 d . . P A
1
Cl3A Cl 0.80754(18) 0.26748(10) 0.86169(15) 0.0549(4) Uani 0.675(3) 1 d . . P A
1
C21B C 0.937(4) 0.233(2) 0.964(4) 0.052(5) Uani 0.325(3) 1 d . . P A 2
H21B H 1.013374 0.265682 0.985913 0.063 Uiso 0.325(3) 1 calc R U P A 2
Cl1B Cl 0.8985(3) 0.2024(3) 1.0946(3) 0.0883(11) Uani 0.325(3) 1 d . . P A 2
Cl2B Cl 0.9655(7) 0.1372(4) 0.9005(6) 0.222(5) Uani 0.325(3) 1 d . . P A 2
Cl3B Cl 0.8323(7) 0.2618(5) 0.8756(9) 0.188(4) Uani 0.325(3) 1 d . . P A 2
S1 S 0.20636(5) 0.18399(3) 0.68032(5) 0.03615(15) Uani 1 1 d . . . . .
O1 O 0.59759(15) 0.34519(8) 0.67331(13) 0.0387(3) Uani 1 1 d . . . . .
O2 O 0.35178(15) 0.17716(7) 0.31090(12) 0.0336(3) Uani 1 1 d . . . . .
H200 H 0.299705 0.211939 0.297727 0.050 Uiso 1 1 calc R U . . .
N1 N 0.30933(16) 0.14498(8) 0.49977(14) 0.0287(3) Uani 1 1 d . . . . .
N2 N 0.39885(17) 0.24099(9) 0.60990(15) 0.0316(4) Uani 1 1 d . . . . .
H2 H 0.410134 0.277513 0.663259 0.038 Uiso 1 1 calc R U . . .
C2 C 0.61750(19) 0.42237(10) 0.51097(18) 0.0296(4) Uani 1 1 d . . . . .
C3 C 0.6960(2) 0.47102(11) 0.5963(2) 0.0373(5) Uani 1 1 d . . . . .
H3 H 0.719520 0.461162 0.683918 0.045 Uiso 1 1 calc R U . . .
C4 C 0.7399(2) 0.53357(12) 0.5543(2) 0.0457(6) Uani 1 1 d . . . . .
H4 H 0.793252 0.566510 0.613117 0.055 Uiso 1 1 calc R U . . .
C5 C 0.7061(2) 0.54817(13) 0.4270(2) 0.0478(6) Uani 1 1 d . . . . .
H5 H 0.737421 0.590719 0.398142 0.057 Uiso 1 1 calc R U . . .
C6 C 0.6270(3) 0.50093(14) 0.3421(2) 0.0501(6) Uani 1 1 d . . . . .
H6 H 0.602878 0.511364 0.254627 0.060 Uiso 1 1 calc R U . . .
C7 C 0.5826(2) 0.43834(12) 0.3835(2) 0.0404(5) Uani 1 1 d . . . . .
H7 H 0.527901 0.406107 0.324321 0.048 Uiso 1 1 calc R U . . .
C8 C 0.57557(18) 0.35488(10) 0.56087(18) 0.0285(4) Uani 1 1 d . . . . .
C9 C 0.5032(2) 0.29787(10) 0.46664(18) 0.0298(4) Uani 1 1 d . . . . .
H9A H 0.420901 0.318879 0.414672 0.036 Uiso 1 1 calc R U . . .
H9B H 0.553280 0.285466 0.409870 0.036 Uiso 1 1 calc R U . . .
C10 C 0.47726(19) 0.22880(10) 0.52876(17) 0.0272(4) Uani 1 1 d . . . . .
C11 C 0.40513(19) 0.16649(10) 0.43974(17) 0.0284(4) Uani 1 1 d . . . . .
C12 C 0.30753(18) 0.19048(10) 0.59446(17) 0.0269(4) Uani 1 1 d . . . . .
C13 C 0.5916(2) 0.17526(11) 0.5804(2) 0.0355(4) Uani 1 1 d . . . . .
H13A H 0.673483 0.194376 0.574529 0.043 Uiso 1 1 calc R U . . .
H13B H 0.601462 0.157215 0.666279 0.043 Uiso 1 1 calc R U . . .
C14 C 0.5260(2) 0.11993(11) 0.4753(2) 0.0379(5) Uani 1 1 d . . . . .
H14A H 0.566583 0.116554 0.408159 0.046 Uiso 1 1 calc R U . . .
H14B H 0.514467 0.070949 0.507347 0.046 Uiso 1 1 calc R U . . .
C15 C 0.23154(19) 0.08131(11) 0.46324(19) 0.0318(4) Uani 1 1 d . . . . .
C16 C 0.2533(2) 0.02196(11) 0.5436(2) 0.0422(5) Uani 1 1 d . . . . .
H16 H 0.318920 0.023708 0.622379 0.051 Uiso 1 1 calc R U . . .
C17 C 0.1790(3) -0.03983(14) 0.5086(3) 0.0602(7) Uani 1 1 d . . . . .
H17 H 0.192841 -0.080371 0.564085 0.072 Uiso 1 1 calc R U . . .
C18 C 0.0857(3) -0.04299(17) 0.3948(3) 0.0730(9) Uani 1 1 d . . . . .
H18 H 0.035258 -0.085757 0.371239 0.088 Uiso 1 1 calc R U . . .
C19 C 0.0646(3) 0.0157(2) 0.3142(3) 0.0783(10) Uani 1 1 d . . . . .
H19 H 0.000291 0.013095 0.234663 0.094 Uiso 1 1 calc R U . . .
C20 C 0.1371(2) 0.07906(16) 0.3487(2) 0.0545(7) Uani 1 1 d . . . . .
H20 H 0.121598 0.120008 0.294026 0.065 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
C21A Cl2A 1.661(15) . ?
C21A Cl1A 1.66(2) . ?
C21A Cl3A 1.899(15) . ?
C21B Cl3B 1.37(3) . ?
C21B Cl1B 1.73(4) . ?
C21B Cl2B 1.96(3) . ?
S1 C12 1.6890(19) . ?
O1 C8 1.218(2) . ?
O2 C11 1.390(2) . ?
N1 C12 1.354(2) . ?
N1 C15 1.431(2) . ?
N1 C11 1.472(2) . ?
N2 C12 1.339(2) . ?
N2 C10 1.454(2) . ?
C2 C7 1.388(3) . ?
C2 C3 1.393(3) . ?
C2 C8 1.490(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.381(3) . ?
C5 C6 1.377(4) . ?
C6 C7 1.384(3) . ?
C8 C9 1.522(3) . ?
C9 C10 1.515(3) . ?
C10 C13 1.560(3) . ?
C10 C11 1.561(3) . ?
C11 C14 1.527(3) . ?
C13 C14 1.550(3) . ?
C15 C20 1.376(3) . ?
C15 C16 1.385(3) . ?
C16 C17 1.382(3) . ?
C17 C18 1.365(5) . ?
C18 C19 1.378(5) . ?
C19 C20 1.395(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2A C21A Cl1A 117.7(9) . . ?
Cl2A C21A Cl3A 109.2(10) . . ?
Cl1A C21A Cl3A 110.7(9) . . ?
Cl3B C21B Cl1B 111(2) . . ?
Cl3B C21B Cl2B 106(2) . . ?
Cl1B C21B Cl2B 97(2) . . ?
C12 N1 C15 124.93(16) . . ?
C12 N1 C11 112.33(15) . . ?
C15 N1 C11 122.70(15) . . ?
C12 N2 C10 112.52(15) . . ?
C7 C2 C3 118.86(18) . . ?
C7 C2 C8 122.81(18) . . ?
C3 C2 C8 118.33(18) . . ?
C4 C3 C2 120.5(2) . . ?
C5 C4 C3 120.1(2) . . ?
C6 C5 C4 119.9(2) . . ?
C5 C6 C7 120.3(2) . . ?
C6 C7 C2 120.4(2) . . ?
O1 C8 C2 121.57(17) . . ?
O1 C8 C9 120.50(17) . . ?
C2 C8 C9 117.93(16) . . ?
C10 C9 C8 112.96(15) . . ?
N2 C10 C9 113.10(15) . . ?
N2 C10 C13 115.81(16) . . ?
C9 C10 C13 116.75(17) . . ?
N2 C10 C11 103.14(15) . . ?
C9 C10 C11 116.82(15) . . ?
C13 C10 C11 88.11(14) . . ?
O2 C11 N1 112.30(16) . . ?
O2 C11 C14 113.65(16) . . ?
N1 C11 C14 115.04(16) . . ?
O2 C11 C10 121.66(15) . . ?
N1 C11 C10 101.56(14) . . ?
C14 C11 C10 90.80(15) . . ?
N2 C12 N1 109.46(16) . . ?
N2 C12 S1 125.39(14) . . ?
N1 C12 S1 125.14(15) . . ?
C14 C13 C10 89.99(15) . . ?
C11 C14 C13 89.66(15) . . ?
C20 C15 C16 120.6(2) . . ?
C20 C15 N1 120.13(19) . . ?
C16 C15 N1 119.30(19) . . ?
C17 C16 C15 119.6(2) . . ?
C18 C17 C16 120.4(3) . . ?
C17 C18 C19 120.1(3) . . ?
C18 C19 C20 120.3(3) . . ?
C15 C20 C19 119.0(3) . . ?

_refine_diff_density_max         0.661
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_5f
_database_code_depnum_ccdc_archive 'CCDC 2361611'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2024-06-10 deposited with the CCDC.	2024-09-06 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H18 N2 O2 S'
_chemical_formula_sum            'C19 H18 N2 O2 S'
_chemical_melting_point          ?


_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         338.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0096 '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 0.0189 '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'
_chemical_absolute_configuration .

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'

_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.
;

_cell_length_a                   14.3538(2)
_cell_length_b                   29.2862(4)
_cell_length_c                   7.77910(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.1680(10)
_cell_angle_gamma                90
_cell_volume                     3261.44(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    8990
_cell_measurement_theta_min      5.70
_cell_measurement_theta_max      64.97
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.875
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8608
_exptl_absorpt_correction_T_max  0.9526
_exptl_absorpt_process_details   'Bruker APEX4'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTONIII c7'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54989
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.319
_diffrn_reflns_theta_max         65.197
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             5541
_reflns_number_gt                5283
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+12.8978P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         5541
_refine_ls_number_parameters     425
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0766
_refine_ls_wR_factor_ref         0.1649
_refine_ls_wR_factor_gt          0.1637
_refine_ls_goodness_of_fit_ref   1.283
_refine_ls_restrained_S_all      1.283
_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
S1 S 0.42729(7) 0.45534(3) 1.22309(12) 0.0203(2) Uani 1 1 d . . . . .
O2 O 0.1802(2) 0.52616(12) 0.7504(4) 0.0339(8) Uani 1 1 d . . . . .
O3 O 0.49197(19) 0.45067(9) 0.6240(3) 0.0193(6) Uani 1 1 d . . . . .
H300 H 0.517516 0.473718 0.671269 0.029 Uiso 1 1 calc R U . . .
N3 N 0.3413(2) 0.48183(12) 0.9177(4) 0.0202(7) Uani 1 1 d . . . . .
H3A H 0.309924 0.504132 0.962700 0.024 Uiso 1 1 calc R U . . .
N4 N 0.4467(2) 0.42848(11) 0.8981(4) 0.0193(7) Uani 1 1 d . . . . .
H4A H 0.487961 0.407581 0.932568 0.023 Uiso 1 1 calc R U . . .
C1 C 0.0022(3) 0.57758(14) -0.0133(5) 0.0218(9) Uani 1 1 d . . . . .
C2 C -0.0854(3) 0.55825(15) -0.0568(6) 0.0254(10) Uani 1 1 d . . . . .
H2 H -0.107924 0.534518 0.012361 0.031 Uiso 1 1 calc R U . . .
C3 C -0.1395(3) 0.57350(16) -0.2000(6) 0.0319(11) Uani 1 1 d . . . . .
H3 H -0.198991 0.560219 -0.228644 0.038 Uiso 1 1 calc R U . . .
C4 C -0.1073(3) 0.60785(16) -0.3011(6) 0.0320(11) Uani 1 1 d . . . . .
H4 H -0.145143 0.618669 -0.397879 0.038 Uiso 1 1 calc R U . . .
C5 C -0.0199(3) 0.62661(16) -0.2615(6) 0.0320(11) Uani 1 1 d . . . . .
H5 H 0.002599 0.649967 -0.332445 0.038 Uiso 1 1 calc R U . . .
C6 C 0.0347(3) 0.61151(15) -0.1194(6) 0.0273(10) Uani 1 1 d . . . . .
H6 H 0.094875 0.624349 -0.093794 0.033 Uiso 1 1 calc R U . . .
C7 C 0.0587(3) 0.56327(13) 0.1453(5) 0.0203(9) Uani 1 1 d . . . . .
C8 C 0.1559(3) 0.56041(14) 0.1491(5) 0.0213(9) Uani 1 1 d . . . . .
H8 H 0.186486 0.566897 0.047597 0.026 Uiso 1 1 calc R U . . .
C9 C 0.2083(3) 0.54830(14) 0.2979(5) 0.0216(9) Uani 1 1 d . . . . .
H9 H 0.274232 0.545794 0.297027 0.026 Uiso 1 1 calc R U . . .
C10 C 0.1648(3) 0.53966(13) 0.4503(5) 0.0207(9) Uani 1 1 d . . . . .
C11 C 0.0682(3) 0.54403(13) 0.4483(6) 0.0230(9) Uani 1 1 d . . . . .
H11 H 0.037924 0.539600 0.551646 0.028 Uiso 1 1 calc R U . . .
C12 C 0.0160(3) 0.55468(14) 0.2986(6) 0.0243(9) Uani 1 1 d . . . . .
H12 H -0.050045 0.556249 0.298919 0.029 Uiso 1 1 calc R U . . .
C13 C 0.2172(3) 0.52556(14) 0.6140(5) 0.0226(9) Uani 1 1 d . . . . .
C14 C 0.3158(3) 0.50726(14) 0.6098(5) 0.0199(8) Uani 1 1 d . . . . .
H14A H 0.326016 0.496231 0.492328 0.024 Uiso 1 1 calc R U . . .
H14B H 0.361200 0.532017 0.638978 0.024 Uiso 1 1 calc R U . . .
C15 C 0.3312(3) 0.46845(13) 0.7376(5) 0.0168(8) Uani 1 1 d . . . . .
C16 C 0.4043(3) 0.45588(13) 1.0060(5) 0.0180(8) Uani 1 1 d . . . . .
C17 C 0.4171(3) 0.43696(14) 0.7166(5) 0.0182(8) Uani 1 1 d . . . . .
C18 C 0.3545(3) 0.40022(14) 0.6314(5) 0.0219(9) Uani 1 1 d . . . . .
H18A H 0.364602 0.369487 0.682403 0.026 Uiso 1 1 calc R U . . .
H18B H 0.355687 0.399185 0.504403 0.026 Uiso 1 1 calc R U . . .
C19 C 0.2686(3) 0.42557(14) 0.6949(6) 0.0229(9) Uani 1 1 d . . . . .
H19A H 0.243456 0.411443 0.797471 0.027 Uiso 1 1 calc R U . . .
H19B H 0.218346 0.430965 0.603222 0.027 Uiso 1 1 calc R U . . .
C20 C 1.2165(3) 0.29769(14) 0.8336(5) 0.0218(9) Uani 1 1 d . . . . .
C21 C 1.2387(3) 0.32760(15) 0.9694(6) 0.0268(10) Uani 1 1 d . . . . .
H21 H 1.190419 0.344892 1.015820 0.032 Uiso 1 1 calc R U . . .
C22 C 1.3303(3) 0.33260(15) 1.0384(6) 0.0297(10) Uani 1 1 d . . . . .
H22 H 1.344465 0.353351 1.130509 0.036 Uiso 1 1 calc R U . . .
C23 C 1.4006(3) 0.30730(17) 0.9724(7) 0.0334(11) Uani 1 1 d . . . . .
H23 H 1.463197 0.310432 1.019507 0.040 Uiso 1 1 calc R U . . .
C24 C 1.3796(3) 0.27730(16) 0.8373(6) 0.0306(11) Uani 1 1 d . . . . .
H24 H 1.427868 0.259830 0.791876 0.037 Uiso 1 1 calc R U . . .
C25 C 1.2883(3) 0.27275(15) 0.7685(6) 0.0267(10) Uani 1 1 d . . . . .
H25 H 1.274581 0.252272 0.675392 0.032 Uiso 1 1 calc R U . . .
C26 C 1.1189(3) 0.29231(14) 0.7593(5) 0.0203(9) Uani 1 1 d . . . . .
C27 C 1.0858(3) 0.25056(15) 0.6929(6) 0.0280(10) Uani 1 1 d . . . . .
H27 H 1.126184 0.224814 0.696266 0.034 Uiso 1 1 calc R U . . .
C28 C 0.9949(3) 0.24626(17) 0.6222(6) 0.0327(11) Uani 1 1 d . . . . .
H28 H 0.974043 0.217792 0.575172 0.039 Uiso 1 1 calc R U . . .
C29 C 0.9336(3) 0.28328(16) 0.6192(6) 0.0274(10) Uani 1 1 d . . . . .
C30 C 0.9658(3) 0.32435(16) 0.6884(6) 0.0319(11) Uani 1 1 d . . . . .
H30 H 0.924695 0.349769 0.689288 0.038 Uiso 1 1 calc R U . . .
C31 C 1.0566(3) 0.32881(14) 0.7559(6) 0.0265(10) Uani 1 1 d . . . . .
H31 H 1.077359 0.357472 0.801258 0.032 Uiso 1 1 calc R U . . .
N1A N 0.5779(3) 0.36432(17) 0.2715(7) 0.0267(5) Uani 0.739(3) 1 d . . P A 1
H1A H 0.526054 0.378813 0.237637 0.032 Uiso 0.739(3) 1 calc R U P A 1
N2A N 0.7035(3) 0.32278(16) 0.2483(6) 0.0215(4) Uani 0.739(3) 1 d . . P A 1
H2A H 0.751592 0.310157 0.202581 0.026 Uiso 0.739(3) 1 calc R U P A 1
O5A O 0.6322(3) 0.39056(13) 0.5466(5) 0.0217(9) Uani 0.739(3) 1 d . . P A 1
H5A H 0.584858 0.404872 0.574460 0.033 Uiso 0.739(3) 1 calc R U P A 1
C32A C 0.8338(5) 0.2806(2) 0.5409(10) 0.0267(5) Uani 0.739(3) 1 d . . P A 1
C33A C 0.7672(4) 0.3195(2) 0.5526(7) 0.0215(4) Uani 0.739(3) 1 d . . P A 1
H33C H 0.800437 0.348316 0.531508 0.026 Uiso 0.739(3) 1 calc R U P A 1
H33D H 0.746457 0.320712 0.671140 0.026 Uiso 0.739(3) 1 calc R U P A 1
C34A C 0.6815(4) 0.3161(2) 0.4255(8) 0.0215(4) Uani 0.739(3) 1 d . . P A 1
C35A C 0.6422(4) 0.3504(2) 0.1625(7) 0.0215(4) Uani 0.739(3) 1 d . . P A 1
C36A C 0.6043(4) 0.3526(2) 0.4502(10) 0.0267(5) Uani 0.739(3) 1 d . . P A 1
C37A C 0.5433(4) 0.3158(2) 0.5264(8) 0.0267(5) Uani 0.739(3) 1 d . . P A 1
H37A H 0.479909 0.313545 0.467693 0.032 Uiso 0.739(3) 1 calc R U P A 1
H37B H 0.540079 0.318380 0.652790 0.032 Uiso 0.739(3) 1 calc R U P A 1
C38A C 0.6135(7) 0.2770(4) 0.4700(15) 0.0267(5) Uani 0.739(3) 1 d . . P A 1
H38C H 0.637892 0.257025 0.565767 0.032 Uiso 0.739(3) 1 calc R U P A 1
H38D H 0.589356 0.258769 0.369216 0.032 Uiso 0.739(3) 1 calc R U P A 1
S2A S 0.6428(2) 0.36928(7) -0.0430(4) 0.0215(4) Uani 0.739(3) 1 d . . P A 1
O4A O 0.8094(3) 0.24500(15) 0.4666(6) 0.0267(5) Uani 0.739(3) 1 d . . P A 1
N1B N 0.6064(10) 0.3684(5) 0.617(2) 0.0267(5) Uani 0.261(3) 1 d . . P A 2
H1B H 0.561960 0.389003 0.621515 0.032 Uiso 0.261(3) 1 calc R U P A 2
N2B N 0.7147(10) 0.3202(5) 0.7149(19) 0.0267(5) Uani 0.261(3) 1 d . . P A 2
H2B H 0.756603 0.307158 0.787143 0.032 Uiso 0.261(3) 1 calc R U P A 2
O5B O 0.6778(9) 0.3828(4) 0.3615(15) 0.032(3) Uani 0.261(3) 1 d . . P A 2
H5B H 0.641674 0.405266 0.347060 0.048 Uiso 0.261(3) 1 calc R U P A 2
C32B C 0.8498(14) 0.2671(7) 0.527(3) 0.0267(5) Uani 0.261(3) 1 d . . P A 2
C34B C 0.6998(12) 0.3092(6) 0.527(2) 0.0267(5) Uani 0.261(3) 1 d . . P A 2
C33B C 0.7911(11) 0.3032(6) 0.447(2) 0.0267(5) Uani 0.261(3) 1 d . . P A 2
H33A H 0.778227 0.295989 0.322773 0.032 Uiso 0.261(3) 1 calc R U P A 2
H33B H 0.825919 0.332385 0.454755 0.032 Uiso 0.261(3) 1 calc R U P A 2
C38B C 0.605(2) 0.2801(11) 0.454(4) 0.0215(4) Uani 0.261(3) 1 d . . P A 2
H38A H 0.619136 0.253688 0.380772 0.026 Uiso 0.261(3) 1 calc R U P A 2
H38B H 0.565006 0.270583 0.546135 0.026 Uiso 0.261(3) 1 calc R U P A 2
S2B S 0.6431(8) 0.3597(3) 0.9505(15) 0.0267(5) Uani 0.261(3) 1 d . . P A 2
C37B C 0.5723(11) 0.3137(5) 0.368(2) 0.0215(4) Uani 0.261(3) 1 d . . P A 2
H37C H 0.505410 0.319179 0.384429 0.026 Uiso 0.261(3) 1 calc R U P A 2
H37D H 0.581987 0.311171 0.243876 0.026 Uiso 0.261(3) 1 calc R U P A 2
C35B C 0.6558(12) 0.3525(6) 0.756(2) 0.0267(5) Uani 0.261(3) 1 d . . P A 2
C36B C 0.6338(12) 0.3481(7) 0.456(2) 0.0215(4) Uani 0.261(3) 1 d . . P A 2
O4B O 0.8172(8) 0.2263(4) 0.5283(17) 0.0267(5) Uani 0.261(3) 1 d . . 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 C16 1.697(4) . ?
O2 C13 1.221(5) . ?
O3 C17 1.395(5) . ?
N3 C16 1.333(5) . ?
N3 C15 1.452(5) . ?
N4 C16 1.339(5) . ?
N4 C17 1.466(5) . ?
C1 C6 1.393(6) . ?
C1 C2 1.398(6) . ?
C1 C7 1.487(6) . ?
C2 C3 1.385(6) . ?
C3 C4 1.377(7) . ?
C4 C5 1.384(7) . ?
C5 C6 1.381(6) . ?
C7 C8 1.396(6) . ?
C7 C12 1.403(6) . ?
C8 C9 1.380(6) . ?
C9 C10 1.402(6) . ?
C10 C11 1.392(6) . ?
C10 C13 1.489(6) . ?
C11 C12 1.373(6) . ?
C13 C14 1.517(6) . ?
C14 C15 1.516(5) . ?
C15 C17 1.558(5) . ?
C15 C19 1.566(6) . ?
C17 C18 1.522(6) . ?
C18 C19 1.550(6) . ?
C20 C25 1.388(6) . ?
C20 C21 1.391(6) . ?
C20 C26 1.485(6) . ?
C21 C22 1.392(6) . ?
C22 C23 1.380(7) . ?
C23 C24 1.386(7) . ?
C24 C25 1.386(6) . ?
C26 C31 1.393(6) . ?
C26 C27 1.397(6) . ?
C27 C28 1.384(7) . ?
C28 C29 1.396(7) . ?
C29 C30 1.383(7) . ?
C29 C32B 1.44(2) . ?
C29 C32A 1.518(8) . ?
C30 C31 1.376(6) . ?
N1A C35A 1.360(7) . ?
N1A C36A 1.455(9) . ?
N2A C35A 1.338(7) . ?
N2A C34A 1.449(7) . ?
O5A C36A 1.384(8) . ?
C32A O4A 1.230(8) . ?
C32A C33A 1.493(8) . ?
C33A C34A 1.525(8) . ?
C34A C38A 1.560(14) . ?
C34A C36A 1.562(8) . ?
C35A S2A 1.692(6) . ?
C36A C37A 1.534(9) . ?
C37A C38A 1.603(12) . ?
N1B C35B 1.34(2) . ?
N1B C36B 1.46(2) . ?
N2B C35B 1.32(2) . ?
N2B C34B 1.50(2) . ?
O5B C36B 1.43(2) . ?
C32B O4B 1.28(2) . ?
C32B C33B 1.46(2) . ?
C34B C33B 1.50(2) . ?
C34B C36B 1.56(2) . ?
C34B C38B 1.67(4) . ?
C38B C37B 1.26(3) . ?
C38B C36B 2.03(4) . ?
S2B C35B 1.55(2) . ?
C37B C36B 1.47(2) . ?

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
C16 N3 C15 111.1(3) . . ?
C16 N4 C17 112.9(3) . . ?
C6 C1 C2 118.6(4) . . ?
C6 C1 C7 120.5(4) . . ?
C2 C1 C7 120.9(4) . . ?
C3 C2 C1 120.4(4) . . ?
C4 C3 C2 120.2(4) . . ?
C3 C4 C5 120.0(4) . . ?
C6 C5 C4 120.2(4) . . ?
C5 C6 C1 120.5(4) . . ?
C8 C7 C12 118.0(4) . . ?
C8 C7 C1 121.2(4) . . ?
C12 C7 C1 120.7(4) . . ?
C9 C8 C7 121.1(4) . . ?
C8 C9 C10 120.4(4) . . ?
C11 C10 C9 118.6(4) . . ?
C11 C10 C13 118.4(4) . . ?
C9 C10 C13 123.0(4) . . ?
C12 C11 C10 120.8(4) . . ?
C11 C12 C7 121.1(4) . . ?
O2 C13 C10 121.0(4) . . ?
O2 C13 C14 119.3(4) . . ?
C10 C13 C14 119.6(3) . . ?
C15 C14 C13 110.0(3) . . ?
N3 C15 C14 115.5(3) . . ?
N3 C15 C17 103.7(3) . . ?
C14 C15 C17 117.0(3) . . ?
N3 C15 C19 115.9(3) . . ?
C14 C15 C19 114.1(3) . . ?
C17 C15 C19 87.1(3) . . ?
N3 C16 N4 110.0(3) . . ?
N3 C16 S1 126.4(3) . . ?
N4 C16 S1 123.6(3) . . ?
O3 C17 N4 111.5(3) . . ?
O3 C17 C18 115.5(3) . . ?
N4 C17 C18 114.8(3) . . ?
O3 C17 C15 121.9(3) . . ?
N4 C17 C15 100.1(3) . . ?
C18 C17 C15 91.0(3) . . ?
C17 C18 C19 88.9(3) . . ?
C18 C19 C15 89.7(3) . . ?
C25 C20 C21 118.3(4) . . ?
C25 C20 C26 120.4(4) . . ?
C21 C20 C26 121.3(4) . . ?
C20 C21 C22 121.1(4) . . ?
C23 C22 C21 119.7(4) . . ?
C22 C23 C24 119.9(4) . . ?
C25 C24 C23 120.1(4) . . ?
C24 C25 C20 121.0(4) . . ?
C31 C26 C27 117.7(4) . . ?
C31 C26 C20 120.8(4) . . ?
C27 C26 C20 121.5(4) . . ?
C28 C27 C26 120.8(4) . . ?
C27 C28 C29 120.7(4) . . ?
C30 C29 C28 118.5(4) . . ?
C30 C29 C32B 136.5(8) . . ?
C28 C29 C32B 104.9(8) . . ?
C30 C29 C32A 118.7(4) . . ?
C28 C29 C32A 122.8(4) . . ?
C31 C30 C29 120.7(4) . . ?
C30 C31 C26 121.6(4) . . ?
C35A N1A C36A 112.5(5) . . ?
C35A N2A C34A 112.0(5) . . ?
O4A C32A C33A 120.9(6) . . ?
O4A C32A C29 117.4(5) . . ?
C33A C32A C29 121.7(5) . . ?
C32A C33A C34A 113.6(5) . . ?
N2A C34A C33A 112.7(5) . . ?
N2A C34A C38A 119.6(6) . . ?
C33A C34A C38A 113.0(5) . . ?
N2A C34A C36A 103.3(5) . . ?
C33A C34A C36A 115.0(5) . . ?
C38A C34A C36A 90.8(6) . . ?
N2A C35A N1A 108.8(5) . . ?
N2A C35A S2A 128.3(4) . . ?
N1A C35A S2A 122.8(4) . . ?
O5A C36A N1A 111.9(5) . . ?
O5A C36A C37A 120.3(6) . . ?
N1A C36A C37A 114.8(5) . . ?
O5A C36A C34A 115.9(5) . . ?
N1A C36A C34A 100.5(5) . . ?
C37A C36A C34A 89.9(5) . . ?
C36A C37A C38A 90.2(6) . . ?
C34A C38A C37A 87.4(7) . . ?
C35B N1B C36B 113.0(14) . . ?
C35B N2B C34B 110.1(14) . . ?
O4B C32B C29 126.7(16) . . ?
O4B C32B C33B 118.4(18) . . ?
C29 C32B C33B 114.3(15) . . ?
N2B C34B C33B 111.4(14) . . ?
N2B C34B C36B 103.2(13) . . ?
C33B C34B C36B 117.8(15) . . ?
N2B C34B C38B 119.9(17) . . ?
C33B C34B C38B 120.8(18) . . ?
C36B C34B C38B 78.0(15) . . ?
C32B C33B C34B 113.5(16) . . ?
C37B C38B C34B 92(2) . . ?
C37B C38B C36B 46.2(15) . . ?
C34B C38B C36B 48.4(12) . . ?
C38B C37B C36B 95.9(19) . . ?
N2B C35B N1B 111.2(15) . . ?
N2B C35B S2B 117.3(14) . . ?
N1B C35B S2B 130.6(14) . . ?
O5B C36B N1B 107.9(15) . . ?
O5B C36B C37B 121.2(15) . . ?
N1B C36B C37B 119.1(15) . . ?
O5B C36B C34B 114.9(14) . . ?
N1B C36B C34B 101.0(14) . . ?
C37B C36B C34B 89.7(14) . . ?
O5B C36B C38B 142.1(16) . . ?
N1B C36B C38B 109.8(15) . . ?
C37B C36B C38B 38.0(10) . . ?
C34B C36B C38B 53.6(11) . . ?

_refine_diff_density_max         0.704
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_6e
_database_code_depnum_ccdc_archive 'CCDC 2361610'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2024-06-10 deposited with the CCDC.	2024-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N2 O2 S'
_chemical_formula_sum            'C20 H20 N2 O2 S'
_chemical_formula_weight         352.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.754(3)
_cell_length_b                   11.915(3)
_cell_length_c                   15.389(4)
_cell_angle_alpha                99.849(8)
_cell_angle_beta                 101.129(8)
_cell_angle_gamma                117.442(8)
_cell_volume                     1791.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    9870
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.34


_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.196
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8814
_exptl_absorpt_correction_T_max  0.9462
_exptl_absorpt_process_details   'Bruker APEX4'

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTONIII c7'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            137955
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_av_R_equivalents  0.1082
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.014
_diffrn_reflns_theta_max         31.039
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             11402
_reflns_number_gt                7095
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0644P)²+0.2251P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         11402
_refine_ls_number_parameters     455
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
S1 S -0.09047(4) 0.03371(5) 0.27813(3) 0.04030(12) Uani 1 1 d . . . . .
S2 S 0.71504(4) 0.45745(5) 0.71345(3) 0.04029(12) Uani 1 1 d . . . . .
O1 O 0.00506(15) -0.07738(14) 0.13880(9) 0.0525(3) Uani 1 1 d . . . . .
O2 O 0.26733(12) 0.28483(12) 0.43565(9) 0.0419(3) Uani 1 1 d . . . . .
H200 H 0.325762 0.292747 0.481310 0.063 Uiso 1 1 calc R U . . .
O3 O 1.00596(15) 0.62628(14) 0.83482(10) 0.0599(4) Uani 1 1 d . . . . .
O4 O 0.76462(13) 0.20672(12) 0.56823(8) 0.0422(3) Uani 1 1 d . . . . .
H400 H 0.786777 0.188901 0.521298 0.063 Uiso 1 1 calc R U . . .
N1 N 0.04841(13) 0.19130(14) 0.44558(9) 0.0359(3) Uani 1 1 d . . . . .
N2 N -0.17523(13) 0.13883(14) 0.40364(9) 0.0332(3) Uani 1 1 d . . . . .
N3 N 0.62085(14) 0.29113(17) 0.54934(11) 0.0516(4) Uani 1 1 d . . . . .
N4 N 0.46230(13) 0.33093(15) 0.59370(10) 0.0396(3) Uani 1 1 d . . . . .
C1 C 0.18231(17) 0.05844(18) 0.08728(11) 0.0374(4) Uani 1 1 d . . . . .
C2 C 0.28706(19) 0.1843(2) 0.09686(13) 0.0457(4) Uani 1 1 d . . . . .
H2 H 0.310574 0.257166 0.147584 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3571(2) 0.2039(2) 0.03283(14) 0.0531(5) Uani 1 1 d . . . . .
H3 H 0.427655 0.290088 0.038979 0.064 Uiso 1 1 calc R U . . .
C4 C 0.3236(2) 0.0968(2) -0.04040(14) 0.0561(5) Uani 1 1 d . . . . .
H4 H 0.372184 0.109683 -0.083999 0.067 Uiso 1 1 calc R U . . .
C5 C 0.2206(2) -0.0279(2) -0.05025(13) 0.0508(5) Uani 1 1 d . . . . .
H5 H 0.198685 -0.100525 -0.100523 0.061 Uiso 1 1 calc R U . . .
C6 C 0.14895(19) -0.0483(2) 0.01202(12) 0.0438(4) Uani 1 1 d . . . . .
H6 H 0.076978 -0.134518 0.004197 0.053 Uiso 1 1 calc R U . . .
C7 C 0.10590(18) 0.03110(18) 0.15491(12) 0.0384(4) Uani 1 1 d . . . . .
C8 C 0.15547(18) 0.13705(18) 0.24588(12) 0.0402(4) Uani 1 1 d . . . . .
H8A H 0.253984 0.176958 0.273289 0.048 Uiso 1 1 calc R U . . .
H8B H 0.138366 0.207919 0.234219 0.048 Uiso 1 1 calc R U . . .
C9 C 0.08539(15) 0.07996(16) 0.31329(10) 0.0318(3) Uani 1 1 d . . . . .
C10 C -0.07689(15) 0.13018(15) 0.38431(10) 0.0289(3) Uani 1 1 d . . . . .
C11 C 0.14785(15) 0.16646(16) 0.41708(10) 0.0300(3) Uani 1 1 d . . . . .
C12 C 0.1117(2) -0.0263(2) 0.34345(13) 0.0505(5) Uani 1 1 d . . . . .
H12A H 0.028917 -0.114064 0.326781 0.061 Uiso 1 1 calc R U . . .
H12B H 0.182629 -0.034610 0.322382 0.061 Uiso 1 1 calc R U . . .
C13 C 0.16077(18) 0.05457(19) 0.44675(12) 0.0417(4) Uani 1 1 d . . . . .
H13A H 0.098872 0.011839 0.481661 0.050 Uiso 1 1 calc R U . . .
H13B H 0.254454 0.081153 0.479994 0.050 Uiso 1 1 calc R U . . .
C14 C -0.29905(15) 0.08061(16) 0.33073(11) 0.0327(3) Uani 1 1 d . . . . .
C15 C -0.41392(18) -0.02668(18) 0.33461(14) 0.0465(4) Uani 1 1 d . . . . .
H15 H -0.407878 -0.066242 0.382612 0.056 Uiso 1 1 calc R U . . .
C16 C -0.5370(2) -0.0761(2) 0.26888(17) 0.0625(6) Uani 1 1 d . . . . .
H16 H -0.615089 -0.149591 0.272007 0.075 Uiso 1 1 calc R U . . .
C17 C -0.5475(2) -0.0199(2) 0.19888(15) 0.0620(6) Uani 1 1 d . . . . .
H17 H -0.632536 -0.054157 0.154023 0.074 Uiso 1 1 calc R U . . .
C18 C -0.4347(2) 0.0858(2) 0.19439(13) 0.0540(5) Uani 1 1 d . . . . .
H18 H -0.441640 0.124503 0.146016 0.065 Uiso 1 1 calc R U . . .
C19 C -0.31010(18) 0.13686(18) 0.25990(12) 0.0414(4) Uani 1 1 d . . . . .
H19 H -0.232423 0.210298 0.256260 0.050 Uiso 1 1 calc R U . . .
C20 C 0.08360(18) 0.2688(2) 0.54030(12) 0.0479(5) Uani 1 1 d . . . . .
H20A H 0.137346 0.245639 0.582502 0.072 Uiso 1 1 calc R U . . .
H20B H 0.001075 0.249777 0.556216 0.072 Uiso 1 1 calc R U . . .
H20C H 0.136161 0.363301 0.546185 0.072 Uiso 1 1 calc R U . . .
C21 C 1.09901(16) 0.51347(18) 0.90584(12) 0.0390(4) Uani 1 1 d . . . . .
C22 C 1.08949(18) 0.39365(19) 0.90842(13) 0.0441(4) Uani 1 1 d . . . . .
H22 H 1.021136 0.314345 0.861509 0.053 Uiso 1 1 calc R U . . .
C23 C 1.1791(2) 0.3887(2) 0.97902(13) 0.0505(5) Uani 1 1 d . . . . .
H23 H 1.170922 0.306072 0.980745 0.061 Uiso 1 1 calc R U . . .
C24 C 1.2794(2) 0.5032(2) 1.04631(13) 0.0559(5) Uani 1 1 d . . . . .
H24 H 1.341871 0.499819 1.093728 0.067 Uiso 1 1 calc R U . . .
C25 C 1.2897(2) 0.6231(2) 1.04513(14) 0.0601(6) Uani 1 1 d . . . . .
H25 H 1.358803 0.702026 1.092056 0.072 Uiso 1 1 calc R U . . .
C26 C 1.1996(2) 0.6287(2) 0.97571(13) 0.0517(5) Uani 1 1 d . . . . .
H26 H 1.206413 0.711237 0.975668 0.062 Uiso 1 1 calc R U . . .
C27 C 1.00820(16) 0.52449(18) 0.82958(12) 0.0405(4) Uani 1 1 d . . . . .
C28 C 0.92146(17) 0.40615(18) 0.74357(13) 0.0438(4) Uani 1 1 d . . . . .
H28A H 0.980433 0.382928 0.716452 0.053 Uiso 1 1 calc R U . . .
H28B H 0.861130 0.329449 0.761584 0.053 Uiso 1 1 calc R U . . .
C29 C 0.83673(15) 0.43092(16) 0.67066(11) 0.0330(3) Uani 1 1 d . . . . .
C30 C 0.58261(15) 0.35062(16) 0.61065(11) 0.0324(3) Uani 1 1 d . . . . .
C31 C 0.75943(14) 0.32189(16) 0.57460(11) 0.0306(3) Uani 1 1 d . . . . .
C32 C 0.9129(2) 0.5297(2) 0.62028(15) 0.0557(5) Uani 1 1 d . . . . .
H32A H 0.888475 0.598774 0.619401 0.067 Uiso 1 1 calc R U . . .
H32B H 1.011976 0.570022 0.643247 0.067 Uiso 1 1 calc R U . . .
C33 C 0.8460(2) 0.4193(2) 0.52891(14) 0.0495(5) Uani 1 1 d . . . . .
H33A H 0.909058 0.396762 0.507238 0.059 Uiso 1 1 calc R U . . .
H33B H 0.793041 0.434668 0.478996 0.059 Uiso 1 1 calc R U . . .
C34 C 0.43215(15) 0.39767(18) 0.66311(12) 0.0386(4) Uani 1 1 d . . . . .
C35 C 0.4431(2) 0.5174(2) 0.66260(16) 0.0577(5) Uani 1 1 d . . . . .
H35 H 0.479701 0.560261 0.619781 0.069 Uiso 1 1 calc R U . . .
C36 C 0.4003(2) 0.5755(3) 0.7251(2) 0.0778(8) Uani 1 1 d . . . . .
H36 H 0.407874 0.658341 0.724749 0.093 Uiso 1 1 calc R U . . .
C37 C 0.3474(2) 0.5142(3) 0.78695(19) 0.0860(10) Uani 1 1 d . . . . .
H37 H 0.318086 0.554109 0.829341 0.103 Uiso 1 1 calc R U . . .
C38 C 0.3372(3) 0.3958(3) 0.78739(18) 0.0819(8) Uani 1 1 d . . . . .
H38 H 0.300447 0.353209 0.830292 0.098 Uiso 1 1 calc R U . . .
C39 C 0.3796(2) 0.3368(3) 0.72618(15) 0.0597(6) Uani 1 1 d . . . . .
H39 H 0.372651 0.254501 0.727440 0.072 Uiso 1 1 calc R U . . .
C40 C 0.52870(19) 0.2013(2) 0.45814(14) 0.0643(7) Uani 1 1 d . . . . .
H40A H 0.579922 0.204561 0.414412 0.097 Uiso 1 1 calc R U . . .
H40B H 0.463592 0.227977 0.436471 0.097 Uiso 1 1 calc R U . . .
H40C H 0.480566 0.110775 0.462140 0.097 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
S1 C10 1.7619(16) . ?
S1 C9 1.8125(16) . ?
S2 C30 1.7551(16) . ?
S2 C29 1.8134(16) . ?
O1 C7 1.226(2) . ?
O2 C11 1.3873(19) . ?
O3 C27 1.214(2) . ?
O4 C31 1.3892(19) . ?
N1 C10 1.3523(18) . ?
N1 C20 1.450(2) . ?
N1 C11 1.4555(19) . ?
N2 C10 1.2912(18) . ?
N2 C14 1.4252(18) . ?
N3 C30 1.3502(19) . ?
N3 C31 1.4475(19) . ?
N3 C40 1.456(2) . ?
N4 C30 1.2859(19) . ?
N4 C34 1.419(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.405(2) . ?
C1 C7 1.484(2) . ?
C2 C3 1.385(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.375(3) . ?
C5 C6 1.374(3) . ?
C7 C8 1.515(2) . ?
C8 C9 1.507(2) . ?
C9 C12 1.556(2) . ?
C9 C11 1.562(2) . ?
C11 C13 1.542(2) . ?
C12 C13 1.548(3) . ?
C14 C15 1.388(2) . ?
C14 C19 1.389(2) . ?
C15 C16 1.381(3) . ?
C16 C17 1.377(3) . ?
C17 C18 1.370(3) . ?
C18 C19 1.389(2) . ?
C21 C22 1.388(3) . ?
C21 C26 1.395(2) . ?
C21 C27 1.494(2) . ?
C22 C23 1.389(3) . ?
C23 C24 1.373(3) . ?
C24 C25 1.381(3) . ?
C25 C26 1.385(3) . ?
C27 C28 1.515(2) . ?
C28 C29 1.513(2) . ?
C29 C32 1.548(3) . ?
C29 C31 1.561(2) . ?
C31 C33 1.531(2) . ?
C32 C33 1.521(3) . ?
C34 C35 1.373(3) . ?
C34 C39 1.381(3) . ?
C35 C36 1.392(3) . ?
C36 C37 1.370(4) . ?
C37 C38 1.361(4) . ?
C38 C39 1.381(3) . ?

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
C10 S1 C9 93.90(7) . . ?
C30 S2 C29 92.88(7) . . ?
C10 N1 C20 123.08(13) . . ?
C10 N1 C11 117.71(13) . . ?
C20 N1 C11 118.92(12) . . ?
C10 N2 C14 118.04(13) . . ?
C30 N3 C31 118.45(14) . . ?
C30 N3 C40 122.14(14) . . ?
C31 N3 C40 119.38(14) . . ?
C30 N4 C34 118.40(14) . . ?
C2 C1 C6 119.15(17) . . ?
C2 C1 C7 122.66(16) . . ?
C6 C1 C7 118.16(17) . . ?
C3 C2 C1 120.34(18) . . ?
C2 C3 C4 119.6(2) . . ?
C5 C4 C3 120.47(19) . . ?
C6 C5 C4 120.54(19) . . ?
C5 C6 C1 119.92(19) . . ?
O1 C7 C1 120.60(16) . . ?
O1 C7 C8 119.76(16) . . ?
C1 C7 C8 119.62(16) . . ?
C9 C8 C7 111.05(15) . . ?
C8 C9 C12 115.10(14) . . ?
C8 C9 C11 117.37(14) . . ?
C12 C9 C11 88.87(12) . . ?
C8 C9 S1 111.96(11) . . ?
C12 C9 S1 114.64(13) . . ?
C11 C9 S1 106.87(10) . . ?
N2 C10 N1 123.22(14) . . ?
N2 C10 S1 124.63(11) . . ?
N1 C10 S1 112.10(11) . . ?
O2 C11 N1 110.45(13) . . ?
O2 C11 C13 116.35(13) . . ?
N1 C11 C13 114.87(13) . . ?
O2 C11 C9 114.18(13) . . ?
N1 C11 C9 109.07(11) . . ?
C13 C11 C9 90.42(12) . . ?
C13 C12 C9 90.41(13) . . ?
C11 C13 C12 89.85(12) . . ?
C15 C14 C19 118.97(15) . . ?
C15 C14 N2 119.75(15) . . ?
C19 C14 N2 121.01(15) . . ?
C16 C15 C14 120.19(19) . . ?
C17 C16 C15 120.7(2) . . ?
C18 C17 C16 119.53(17) . . ?
C17 C18 C19 120.62(19) . . ?
C18 C19 C14 120.03(18) . . ?
C22 C21 C26 118.80(17) . . ?
C22 C21 C27 122.52(15) . . ?
C26 C21 C27 118.65(17) . . ?
C21 C22 C23 120.55(18) . . ?
C24 C23 C22 120.1(2) . . ?
C23 C24 C25 120.08(18) . . ?
C24 C25 C26 120.19(19) . . ?
C25 C26 C21 120.27(19) . . ?
O3 C27 C21 121.32(16) . . ?
O3 C27 C28 120.51(16) . . ?
C21 C27 C28 118.14(15) . . ?
C29 C28 C27 113.02(15) . . ?
C28 C29 C32 116.74(15) . . ?
C28 C29 C31 116.44(13) . . ?
C32 C29 C31 88.16(13) . . ?
C28 C29 S2 110.54(12) . . ?
C32 C29 S2 115.12(13) . . ?
C31 C29 S2 108.01(10) . . ?
N4 C30 N3 122.81(15) . . ?
N4 C30 S2 124.68(12) . . ?
N3 C30 S2 112.50(11) . . ?
O4 C31 N3 110.42(14) . . ?
O4 C31 C33 117.09(14) . . ?
N3 C31 C33 113.36(14) . . ?
O4 C31 C29 116.45(12) . . ?
N3 C31 C29 107.79(12) . . ?
C33 C31 C29 90.16(13) . . ?
C33 C32 C29 91.02(14) . . ?
C32 C33 C31 90.24(14) . . ?
C35 C34 C39 119.53(18) . . ?
C35 C34 N4 120.16(18) . . ?
C39 C34 N4 120.03(18) . . ?
C34 C35 C36 119.7(2) . . ?
C37 C36 C35 120.4(2) . . ?
C38 C37 C36 119.6(2) . . ?
C37 C38 C39 120.7(3) . . ?
C38 C39 C34 119.9(2) . . ?

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.048

