# Electronic Supplementary Material (ESI) for Green 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_FINAL_MP2_a
_database_code_depnum_ccdc_archive 'CCDC 2239522'
_audit_update_record             
;
2023-02-02 deposited with the CCDC.	2024-01-10 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         ?
_chemical_formula_sum            'C20 H20 N20 O20 S20'
_chemical_formula_weight         1501.76

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   10.3627(7)
_cell_length_b                   10.8980(8)
_cell_length_c                   14.0931(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.6920(10)
_cell_angle_gamma                90
_cell_volume                     1568.86(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.760
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18098
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.733
_diffrn_reflns_theta_max         25.983
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3073
_reflns_number_gt                2568
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)²+0.9566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3073
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   0.779
_refine_ls_restrained_S_all      0.779
_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 0.41690(5) 0.81348(5) 0.51379(4) 0.0567(2) Uani 1 1 d . . . . .
O2 O 0.95670(14) 0.83285(12) 0.57164(9) 0.0474(3) Uani 1 1 d . . . . .
H002 H 0.969208 0.906911 0.577991 0.071 Uiso 1 1 calc R U . . .
O1 O 1.03212(14) 0.92123(12) 0.38881(10) 0.0522(4) Uani 1 1 d . . . . .
O3 O 0.72526(14) 0.86368(14) 0.28074(9) 0.0535(4) Uani 1 1 d . . . . .
N2 N 0.66941(14) 0.87577(13) 0.51866(10) 0.0380(3) Uani 1 1 d . . . . .
N1 N 0.99239(14) 0.71617(14) 0.36321(11) 0.0400(3) Uani 1 1 d . . . . .
N3 N 0.56380(15) 0.83165(14) 0.37267(11) 0.0432(4) Uani 1 1 d . . . . .
C8 C 0.97720(16) 0.82528(16) 0.40446(13) 0.0382(4) Uani 1 1 d . . . . .
C6 C 0.85030(17) 0.67424(15) 0.46764(13) 0.0378(4) Uani 1 1 d . . . . .
C10 C 0.76469(16) 0.89398(15) 0.45535(12) 0.0354(4) Uani 1 1 d . . . . .
H00A H 0.792745 0.979945 0.457193 0.042 Uiso 1 1 calc R U . . .
C1 C 0.91405(17) 0.62520(16) 0.39724(13) 0.0400(4) Uani 1 1 d . . . . .
C7 C 0.88516(17) 0.80864(15) 0.47909(12) 0.0360(4) Uani 1 1 d . . . . .
C11 C 0.68644(17) 0.86357(16) 0.35729(13) 0.0392(4) Uani 1 1 d . . . . .
C12 C 0.55269(18) 0.84082(15) 0.46978(14) 0.0410(4) Uani 1 1 d . . . . .
C13 C 0.6918(2) 0.90639(19) 0.62094(13) 0.0501(5) Uani 1 1 d . . . . .
H00B H 0.611603 0.934623 0.638954 0.075 Uiso 1 1 calc R U . . .
H00C H 0.756773 0.969842 0.633247 0.075 Uiso 1 1 calc R U . . .
H00D H 0.721920 0.834853 0.657904 0.075 Uiso 1 1 calc R U . . .
C5 C 0.7705(2) 0.60101(18) 0.51322(15) 0.0494(5) Uani 1 1 d . . . . .
H00G H 0.728984 0.632477 0.561515 0.059 Uiso 1 1 calc R U . . .
C2 C 0.8997(2) 0.50407(18) 0.36867(16) 0.0532(5) Uani 1 1 d . . . . .
H00H H 0.942877 0.472099 0.321427 0.064 Uiso 1 1 calc R U . . .
C9 C 1.0816(2) 0.6957(2) 0.29514(16) 0.0567(5) Uani 1 1 d . . . . .
H00E H 1.035267 0.706226 0.230690 0.085 Uiso 1 1 calc R U . . .
H00F H 1.115987 0.613882 0.302744 0.085 Uiso 1 1 calc R U . . .
H00I H 1.152250 0.753659 0.307130 0.085 Uiso 1 1 calc R U . . .
C4 C 0.7541(2) 0.47884(19) 0.48481(18) 0.0597(6) Uani 1 1 d . . . . .
H00J H 0.699856 0.428223 0.513820 0.072 Uiso 1 1 calc R U . . .
C3 C 0.8172(2) 0.43219(19) 0.41429(18) 0.0617(6) Uani 1 1 d . . . . .
H00K H 0.804483 0.350321 0.396553 0.074 Uiso 1 1 calc R U . . .
C14 C 0.4633(2) 0.7812(2) 0.29690(17) 0.0616(6) Uani 1 1 d . . . . .
H00L H 0.480059 0.808516 0.234609 0.074 Uiso 1 1 calc R U . . .
H00M H 0.378155 0.812089 0.305249 0.074 Uiso 1 1 calc R U . . .
C15 C 0.4616(3) 0.6428(2) 0.2991(2) 0.0785(8) Uani 1 1 d . . . . .
H00N H 0.546494 0.611973 0.292771 0.118 Uiso 1 1 calc R U . . .
H00O H 0.397772 0.612800 0.246910 0.118 Uiso 1 1 calc R U . . .
H00P H 0.439361 0.615495 0.359112 0.118 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 C12 1.6575(18) . ?
O2 C7 1.412(2) . ?
O1 C8 1.228(2) . ?
O3 C11 1.213(2) . ?
N2 C12 1.342(2) . ?
N2 C10 1.452(2) . ?
N2 C13 1.460(2) . ?
N1 C8 1.344(2) . ?
N1 C1 1.415(2) . ?
N1 C9 1.457(2) . ?
N3 C11 1.370(2) . ?
N3 C12 1.396(2) . ?
N3 C14 1.467(3) . ?
C8 C7 1.545(2) . ?
C6 C5 1.383(3) . ?
C6 C1 1.388(3) . ?
C6 C7 1.511(2) . ?
C10 C11 1.516(2) . ?
C10 C7 1.547(2) . ?
C1 C2 1.381(3) . ?
C5 C4 1.392(3) . ?
C2 C3 1.394(3) . ?
C4 C3 1.376(3) . ?
C14 C15 1.509(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
C12 N2 C10 111.76(14) . . ?
C12 N2 C13 123.48(15) . . ?
C10 N2 C13 124.34(14) . . ?
C8 N1 C1 110.94(15) . . ?
C8 N1 C9 123.59(16) . . ?
C1 N1 C9 125.44(16) . . ?
C11 N3 C12 111.64(15) . . ?
C11 N3 C14 122.95(16) . . ?
C12 N3 C14 125.07(16) . . ?
O1 C8 N1 125.73(17) . . ?
O1 C8 C7 125.45(16) . . ?
N1 C8 C7 108.73(14) . . ?
C5 C6 C1 120.23(17) . . ?
C5 C6 C7 131.37(17) . . ?
C1 C6 C7 108.40(15) . . ?
N2 C10 C11 102.45(13) . . ?
N2 C10 C7 113.10(14) . . ?
C11 C10 C7 110.72(13) . . ?
C2 C1 C6 122.39(18) . . ?
C2 C1 N1 127.62(18) . . ?
C6 C1 N1 109.98(15) . . ?
O2 C7 C6 111.01(14) . . ?
O2 C7 C8 108.58(14) . . ?
C6 C7 C8 101.83(13) . . ?
O2 C7 C10 111.49(14) . . ?
C6 C7 C10 112.95(14) . . ?
C8 C7 C10 110.50(13) . . ?
O3 C11 N3 126.61(17) . . ?
O3 C11 C10 127.14(16) . . ?
N3 C11 C10 106.22(14) . . ?
N2 C12 N3 107.90(15) . . ?
N2 C12 S1 127.40(15) . . ?
N3 C12 S1 124.70(14) . . ?
C6 C5 C4 118.17(19) . . ?
C1 C2 C3 116.5(2) . . ?
C3 C4 C5 120.74(19) . . ?
C4 C3 C2 121.91(19) . . ?
N3 C14 C15 111.7(2) . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.050



####################################################################### 
# 
# 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_sr
_database_code_depnum_ccdc_archive 'CCDC 2289809'
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;
_audit_creation_date             2023-07-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N3 O2 S'
_chemical_formula_sum            'C14 H13 N3 O2 S'
_chemical_formula_weight         287.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.0626(12)
_cell_length_b                   7.5356(5)
_cell_length_c                   21.0257(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.637(2)
_cell_angle_gamma                90
_cell_volume                     2647.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4815
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.907
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1392 before and 0.0906 after correction.
The Ratio of minimum to maximum transmission is 0.8124.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2323
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.437
_diffrn_ambient_temperature      293.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1664
_reflns_number_total             2323
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0709
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0903P)²+0.2286P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1631
_refine_ls_wR_factor_ref         0.1799
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.679(3)
 0.321(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Riding coordinates:
 N1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.11763(8) 0.33883(18) 0.01857(5) 0.0590(5) Uani 1 1 d . . . . .
O1 O 0.40478(17) 0.2304(4) 0.18840(13) 0.0477(8) Uani 1 1 d . . . . .
O2 O 0.12264(18) 0.2112(4) 0.25089(14) 0.0562(9) Uani 1 1 d . . . . .
N1 N 0.4240(2) 0.2465(4) 0.29993(16) 0.0414(9) Uani 1 1 d . . . . .
H1 H 0.472965 0.221543 0.300547 0.050 Uiso 1 1 d R U . . .
N2 N 0.2255(2) 0.3380(4) 0.13147(14) 0.0372(8) Uani 1 1 d . . . . .
N3 N 0.1039(2) 0.2535(5) 0.14060(15) 0.0430(9) Uani 1 1 d . . . . .
C6 C 0.3792(2) 0.2834(5) 0.34654(19) 0.0365(10) Uani 1 1 d . . . . .
C13 C 0.0191(3) 0.1986(6) 0.1240(2) 0.0552(13) Uani 1 1 d . . . . .
H13A H 0.008449 0.141535 0.081743 0.066 Uiso 1 1 calc R U . . .
H13B H 0.008335 0.113491 0.155729 0.066 Uiso 1 1 calc R U . . .
C1 C 0.4040(3) 0.2950(6) 0.4126(2) 0.0478(12) Uani 1 1 d . . . . .
H1A H 0.456152 0.265372 0.432470 0.057 Uiso 1 1 calc R U . . .
C5 C 0.2990(2) 0.3197(5) 0.31585(18) 0.0336(10) Uani 1 1 d . . . . .
C2 C 0.3495(3) 0.3522(6) 0.4493(2) 0.0490(12) Uani 1 1 d . . . . .
H2 H 0.365256 0.361111 0.494173 0.059 Uiso 1 1 calc R U . . .
C7 C 0.3796(2) 0.2603(5) 0.23860(19) 0.0350(9) Uani 1 1 d . . . . .
C9 C 0.2304(2) 0.3066(5) 0.19674(18) 0.0335(9) Uani 1 1 d . . . . .
C8 C 0.2959(2) 0.3032(5) 0.24552(19) 0.0337(9) Uani 1 1 d . . . . .
C3 C 0.2716(3) 0.3961(6) 0.4194(2) 0.0485(12) Uani 1 1 d . . . . .
H3 H 0.236317 0.436893 0.444564 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2458(2) 0.3801(5) 0.35293(18) 0.0377(10) Uani 1 1 d . . . . .
H4 H 0.193578 0.409521 0.333368 0.045 Uiso 1 1 calc R U . . .
C11 C 0.1492(3) 0.3104(6) 0.09632(19) 0.0413(11) Uani 1 1 d . . . . .
C12 C 0.2860(3) 0.4286(6) 0.1029(2) 0.0500(12) Uani 1 1 d . . . . .
H12A H 0.318472 0.502066 0.135089 0.075 Uiso 1 1 calc R U . . .
H12B H 0.260041 0.500957 0.067197 0.075 Uiso 1 1 calc R U . . .
H12C H 0.319118 0.342119 0.087522 0.075 Uiso 1 1 calc R U . . .
C10 C 0.1474(2) 0.2550(6) 0.20261(19) 0.0370(10) Uani 1 1 d . . . . .
C14 C -0.0342(3) 0.3537(7) 0.1227(3) 0.0705(15) Uani 1 1 d . . . . .
H14A H -0.088994 0.315354 0.112283 0.106 Uiso 1 1 calc R U . . .
H14B H -0.024506 0.436576 0.090523 0.106 Uiso 1 1 calc R U . . .
H14C H -0.023862 0.409838 0.164568 0.106 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 C11 1.629(4) . ?
O1 C7 1.238(4) . ?
O2 C10 1.221(5) . ?
N1 H1 0.8536 . ?
N1 C6 1.388(5) . ?
N1 C7 1.361(5) . ?
N2 C9 1.378(5) . ?
N2 C11 1.377(5) . ?
N2 C12 1.465(5) . ?
N3 C13 1.478(6) . ?
N3 C11 1.392(5) . ?
N3 C10 1.364(5) . ?
C6 C1 1.371(5) . ?
C6 C5 1.416(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.478(6) . ?
C1 H1A 0.9300 . ?
C1 C2 1.391(6) . ?
C5 C8 1.474(5) . ?
C5 C4 1.388(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(6) . ?
C7 C8 1.499(5) . ?
C9 C8 1.357(5) . ?
C9 C10 1.498(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(5) . ?
C4 H4 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 N1 H1 135.3 . . ?
C7 N1 H1 112.8 . . ?
C7 N1 C6 111.9(3) . . ?
C9 N2 C12 125.6(3) . . ?
C11 N2 C9 111.7(3) . . ?
C11 N2 C12 121.2(3) . . ?
C11 N3 C13 125.2(3) . . ?
C10 N3 C13 123.1(4) . . ?
C10 N3 C11 111.6(3) . . ?
N1 C6 C5 109.7(3) . . ?
C1 C6 N1 128.8(4) . . ?
C1 C6 C5 121.5(4) . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 N3 110.7(4) . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C6 C1 H1A 120.8 . . ?
C6 C1 C2 118.4(4) . . ?
C2 C1 H1A 120.8 . . ?
C6 C5 C8 106.1(3) . . ?
C4 C5 C6 119.2(4) . . ?
C4 C5 C8 134.1(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
O1 C7 N1 124.8(4) . . ?
O1 C7 C8 128.5(4) . . ?
N1 C7 C8 106.5(3) . . ?
N2 C9 C10 104.9(3) . . ?
C8 C9 N2 129.2(4) . . ?
C8 C9 C10 125.6(3) . . ?
C5 C8 C7 105.9(3) . . ?
C9 C8 C5 127.9(4) . . ?
C9 C8 C7 125.9(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H3 119.5 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
N2 C11 S1 127.2(3) . . ?
N2 C11 N3 106.2(3) . . ?
N3 C11 S1 126.6(3) . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C10 N3 125.4(4) . . ?
O2 C10 C9 129.1(4) . . ?
N3 C10 C9 105.3(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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 C7 C8 C5 178.0(4) . . . . ?
O1 C7 C8 C9 4.2(7) . . . . ?
N1 C6 C1 C2 173.3(4) . . . . ?
N1 C6 C5 C8 0.0(4) . . . . ?
N1 C6 C5 C4 -172.5(3) . . . . ?
N1 C7 C8 C5 2.4(4) . . . . ?
N1 C7 C8 C9 -171.3(4) . . . . ?
N2 C9 C8 C5 161.2(4) . . . . ?
N2 C9 C8 C7 -26.5(6) . . . . ?
N2 C9 C10 O2 178.3(4) . . . . ?
N2 C9 C10 N3 2.7(4) . . . . ?
C6 N1 C7 O1 -178.3(4) . . . . ?
C6 N1 C7 C8 -2.6(4) . . . . ?
C6 C1 C2 C3 0.1(7) . . . . ?
C6 C5 C8 C7 -1.5(4) . . . . ?
C6 C5 C8 C9 172.1(4) . . . . ?
C6 C5 C4 C3 -2.8(6) . . . . ?
C13 N3 C11 S1 3.6(6) . . . . ?
C13 N3 C11 N2 -176.5(4) . . . . ?
C13 N3 C10 O2 0.5(7) . . . . ?
C13 N3 C10 C9 176.3(4) . . . . ?
C1 C6 C5 C8 177.0(3) . . . . ?
C1 C6 C5 C4 4.5(6) . . . . ?
C1 C2 C3 C4 1.6(7) . . . . ?
C5 C6 C1 C2 -3.1(6) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C7 N1 C6 C1 -175.1(4) . . . . ?
C7 N1 C6 C5 1.7(5) . . . . ?
C9 N2 C11 S1 177.9(3) . . . . ?
C9 N2 C11 N3 -1.9(4) . . . . ?
C8 C5 C4 C3 -172.7(4) . . . . ?
C8 C9 C10 O2 4.4(7) . . . . ?
C8 C9 C10 N3 -171.2(4) . . . . ?
C4 C5 C8 C7 169.4(4) . . . . ?
C4 C5 C8 C9 -17.0(7) . . . . ?
C11 N2 C9 C8 173.2(4) . . . . ?
C11 N2 C9 C10 -0.4(4) . . . . ?
C11 N3 C13 C14 -87.3(5) . . . . ?
C11 N3 C10 O2 -179.8(4) . . . . ?
C11 N3 C10 C9 -4.0(5) . . . . ?
C12 N2 C9 C8 -20.5(6) . . . . ?
C12 N2 C9 C10 165.9(4) . . . . ?
C12 N2 C11 S1 10.9(6) . . . . ?
C12 N2 C11 N3 -169.0(3) . . . . ?
C10 N3 C13 C14 92.3(5) . . . . ?
C10 N3 C11 S1 -176.0(3) . . . . ?
C10 N3 C11 N2 3.8(5) . . . . ?
C10 C9 C8 C5 -26.4(6) . . . . ?
C10 C9 C8 C7 145.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.679(3)
2 0.321(3)

####################################################################### 
# 
# 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_MP_a
_database_code_depnum_ccdc_archive 'CCDC 2240661'
_audit_update_record             
;
2023-08-21 deposited with the CCDC.	2024-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 Cl N2 O4 S, C2 H3 O S'
_chemical_formula_sum            'C21 H18 Cl N2 O5 S2'
_chemical_formula_weight         477.94

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.7787(6)
_cell_length_b                   10.3552(6)
_cell_length_c                   11.3624(7)
_cell_angle_alpha                90
_cell_angle_beta                 116.810(2)
_cell_angle_gamma                90
_cell_volume                     1131.90(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5930
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      25.09

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             494
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.388
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Mo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13187
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.117
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3995
_reflns_number_gt                3339
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0863P)²+0.5758P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1343 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.43(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3995
_refine_ls_number_parameters     294
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   0.804
_refine_ls_restrained_S_all      0.804
_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 0.66332(14) 0.07932(11) 0.72702(13) 0.0532(3) Uani 1 1 d . . . A 2
Cl1 Cl 0.9035(2) 0.0296(3) 0.3647(3) 0.1465(13) Uani 1 1 d . . . B 2
S2 S 0.5688(3) 0.8533(3) 0.8991(3) 0.0594(10) Uani 0.501(5) 1 d . . P C 1
O5 O 0.7324(3) 0.4908(3) 0.5405(3) 0.0494(8) Uani 1 1 d . . . . .
O1 O 0.4770(3) 0.5597(3) 0.7490(3) 0.0471(8) Uani 1 1 d . . . . .
H1 H 0.494803 0.602522 0.815460 0.071 Uiso 1 1 calc R U . . .
O3 O 0.5474(3) 0.7482(3) 0.5999(3) 0.0529(9) Uani 1 1 d . . . . .
N1 N 0.5499(4) 0.3162(3) 0.6745(3) 0.0373(8) Uani 1 1 d . . . . .
O2 O 0.7398(4) 0.4467(4) 0.9415(3) 0.0630(10) Uani 1 1 d . . . . .
N2 N 0.7369(3) 0.2970(3) 0.6433(3) 0.0358(8) Uani 1 1 d . . . . .
O4 O 0.5647(5) 0.7196(4) 0.9538(4) 0.0883(14) Uani 1 1 d . . . . .
C10 C 0.5670(4) 0.4416(4) 0.6269(4) 0.0338(9) Uani 1 1 d . . . . .
H10 H 0.483434 0.462821 0.545764 0.041 Uiso 1 1 calc R U . . .
C11 C 0.6877(4) 0.4181(4) 0.5948(4) 0.0366(9) Uani 1 1 d . . . . .
C1 C 0.5966(4) 0.5506(4) 0.7291(4) 0.0341(9) Uani 1 1 d . . . . .
C12 C 0.8504(4) 0.2350(4) 0.6323(4) 0.0380(10) Uani 1 1 d . . . . .
C2 C 0.7310(5) 0.5225(4) 0.8573(4) 0.0414(10) Uani 1 1 d . . . . .
C18 C 0.6482(4) 0.2330(4) 0.6829(4) 0.0375(9) Uani 1 1 d . . . . .
C5 C 0.6324(4) 0.6772(4) 0.6814(4) 0.0385(10) Uani 1 1 d . . . . .
C4 C 0.7834(4) 0.6977(4) 0.7548(4) 0.0406(10) Uani 1 1 d . . . . .
C3 C 0.8402(5) 0.6088(4) 0.8575(4) 0.0431(11) Uani 1 1 d . . . . .
C19 C 0.4234(5) 0.2767(5) 0.6828(6) 0.0561(13) Uani 1 1 d . . . . .
H19A H 0.380837 0.205823 0.623734 0.084 Uiso 1 1 calc R U . . .
H19B H 0.359726 0.347954 0.658722 0.084 Uiso 1 1 calc R U . . .
H19C H 0.446909 0.250395 0.771404 0.084 Uiso 1 1 calc R U . . .
C17 C 0.8245(5) 0.1718(6) 0.5173(5) 0.0539(13) Uani 1 1 d . . . . .
H17 H 0.735573 0.169213 0.447293 0.065 Uiso 1 1 calc R U . . .
C9 C 0.9817(5) 0.6108(5) 0.9455(5) 0.0576(14) Uani 1 1 d . . . . .
H9 H 1.020095 0.551080 1.013697 0.069 Uiso 1 1 calc R U . . .
C13 C 0.9823(5) 0.2371(6) 0.7364(5) 0.0559(13) Uani 1 1 d . . . . .
H13 H 0.998858 0.279721 0.814191 0.067 Uiso 1 1 calc R U . . .
C15 C 1.0663(5) 0.1128(5) 0.6095(6) 0.0638(15) Uani 1 1 d . . . . .
H15 H 1.138538 0.071887 0.600799 0.077 Uiso 1 1 calc R U . . .
C7 C 1.0050(6) 0.7942(6) 0.8260(6) 0.0676(15) Uani 1 1 d . . . . .
H7 H 1.061571 0.857116 0.816894 0.081 Uiso 1 1 calc R U . . .
C6 C 0.8651(5) 0.7915(5) 0.7383(5) 0.0549(12) Uani 1 1 d . . . . .
H6 H 0.827213 0.851202 0.670008 0.066 Uiso 1 1 calc R U . . .
C16 C 0.9350(5) 0.1121(6) 0.5089(6) 0.0627(15) Uani 1 1 d . . . . .
C8 C 1.0625(6) 0.7049(6) 0.9274(6) 0.0705(16) Uani 1 1 d . . . . .
H8 H 1.157183 0.708296 0.984190 0.085 Uiso 1 1 calc R U . . .
C14 C 1.0895(5) 0.1754(7) 0.7243(6) 0.0695(16) Uani 1 1 d . . . . .
H14 H 1.178397 0.176151 0.794541 0.083 Uiso 1 1 calc R U . . .
C21 C 0.6410(11) 0.9567(8) 1.0305(8) 0.114(3) Uani 1 1 d . . . . .
H21A H 0.595594 0.946053 1.085759 0.172 Uiso 0.501(5) 1 calc R U P C 1
H21C H 0.629555 1.044053 0.999135 0.172 Uiso 0.501(5) 1 calc R U P C 1
H21B H 0.738180 0.937848 1.080386 0.172 Uiso 0.501(5) 1 calc R U P C 1
C20 C 0.3963(9) 0.9087(11) 0.8274(10) 0.120(3) Uani 1 1 d . . . . .
H20A H 0.350784 0.884282 0.736118 0.180 Uiso 0.501(5) 1 calc R U P C 1
H20B H 0.395584 1.001047 0.834490 0.180 Uiso 0.501(5) 1 calc R U P C 1
H20C H 0.348204 0.871046 0.872439 0.180 Uiso 0.501(5) 1 calc R U P C 1
S3 S 0.5099(4) 0.8378(3) 0.9790(3) 0.0781(13) Uani 0.499(5) 1 d . . P C 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 C18 1.654(4) . ?
Cl1 C16 1.741(5) . ?
S2 O4 1.526(5) . ?
S2 C21 1.713(8) . ?
S2 C20 1.756(9) . ?
O5 C11 1.203(5) . ?
O1 C1 1.409(5) . ?
O1 H1 0.8200 . ?
O3 C5 1.213(5) . ?
N1 C18 1.335(6) . ?
N1 C10 1.451(5) . ?
N1 C19 1.467(6) . ?
O2 C2 1.208(6) . ?
N2 C11 1.376(5) . ?
N2 C18 1.394(6) . ?
N2 C12 1.436(5) . ?
O4 S3 1.443(5) . ?
C10 C11 1.520(6) . ?
C10 C1 1.546(6) . ?
C10 H10 0.9800 . ?
C1 C5 1.533(6) . ?
C1 C2 1.550(6) . ?
C12 C17 1.373(6) . ?
C12 C13 1.380(6) . ?
C2 C3 1.477(7) . ?
C5 C4 1.472(6) . ?
C4 C6 1.379(7) . ?
C4 C3 1.392(6) . ?
C3 C9 1.397(7) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C17 C16 1.382(7) . ?
C17 H17 0.9300 . ?
C9 C8 1.383(8) . ?
C9 H9 0.9300 . ?
C13 C14 1.381(8) . ?
C13 H13 0.9300 . ?
C15 C16 1.360(8) . ?
C15 C14 1.375(8) . ?
C15 H15 0.9300 . ?
C7 C6 1.383(8) . ?
C7 C8 1.386(9) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C8 H8 0.9300 . ?
C14 H14 0.9300 . ?
C21 S3 1.763(10) . ?
C21 H21A 0.9600 . ?
C21 H21C 0.9600 . ?
C21 H21B 0.9600 . ?
C20 S3 1.761(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
O4 S2 C21 107.3(4) . . ?
O4 S2 C20 105.5(4) . . ?
C21 S2 C20 99.8(6) . . ?
C1 O1 H1 109.5 . . ?
C18 N1 C10 112.0(3) . . ?
C18 N1 C19 123.1(4) . . ?
C10 N1 C19 123.5(4) . . ?
C11 N2 C18 111.5(3) . . ?
C11 N2 C12 124.2(4) . . ?
C18 N2 C12 123.4(3) . . ?
N1 C10 C11 102.3(3) . . ?
N1 C10 C1 113.0(3) . . ?
C11 C10 C1 112.8(3) . . ?
N1 C10 H10 109.5 . . ?
C11 C10 H10 109.5 . . ?
C1 C10 H10 109.5 . . ?
O5 C11 N2 127.2(4) . . ?
O5 C11 C10 127.4(4) . . ?
N2 C11 C10 105.4(3) . . ?
O1 C1 C5 113.2(3) . . ?
O1 C1 C10 106.0(3) . . ?
C5 C1 C10 111.0(3) . . ?
O1 C1 C2 113.3(3) . . ?
C5 C1 C2 102.4(3) . . ?
C10 C1 C2 111.0(3) . . ?
C17 C12 C13 120.8(4) . . ?
C17 C12 N2 118.8(4) . . ?
C13 C12 N2 120.4(4) . . ?
O2 C2 C3 127.9(4) . . ?
O2 C2 C1 125.0(4) . . ?
C3 C2 C1 107.1(4) . . ?
N1 C18 N2 107.9(4) . . ?
N1 C18 S1 127.5(3) . . ?
N2 C18 S1 124.6(3) . . ?
O3 C5 C4 127.3(4) . . ?
O3 C5 C1 124.4(4) . . ?
C4 C5 C1 108.3(3) . . ?
C6 C4 C3 120.9(4) . . ?
C6 C4 C5 129.4(4) . . ?
C3 C4 C5 109.6(4) . . ?
C4 C3 C9 121.0(4) . . ?
C4 C3 C2 110.5(4) . . ?
C9 C3 C2 128.4(4) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C17 C16 117.9(4) . . ?
C12 C17 H17 121.1 . . ?
C16 C17 H17 121.1 . . ?
C8 C9 C3 117.5(5) . . ?
C8 C9 H9 121.3 . . ?
C3 C9 H9 121.3 . . ?
C12 C13 C14 119.5(5) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C16 C15 C14 118.3(5) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C6 C7 C8 121.3(5) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C4 C6 C7 118.1(5) . . ?
C4 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C15 C16 C17 122.8(5) . . ?
C15 C16 Cl1 118.7(4) . . ?
C17 C16 Cl1 118.5(4) . . ?
C9 C8 C7 121.2(5) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C15 C14 C13 120.7(5) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
S2 C21 H21A 109.5 . . ?
S2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
S2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21C C21 H21B 109.5 . . ?
S2 C20 H20A 109.5 . . ?
S2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
S2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 S3 C20 109.0(4) . . ?
O4 S3 C21 108.6(5) . . ?
C20 S3 C21 97.7(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
C18 N1 C10 C11 5.0(4) . . . . ?
C19 N1 C10 C11 -161.8(4) . . . . ?
C18 N1 C10 C1 -116.7(4) . . . . ?
C19 N1 C10 C1 76.6(5) . . . . ?
C18 N2 C11 O5 -171.5(4) . . . . ?
C12 N2 C11 O5 -2.3(7) . . . . ?
C18 N2 C11 C10 9.7(4) . . . . ?
C12 N2 C11 C10 178.9(4) . . . . ?
N1 C10 C11 O5 172.6(4) . . . . ?
C1 C10 C11 O5 -65.7(6) . . . . ?
N1 C10 C11 N2 -8.6(4) . . . . ?
C1 C10 C11 N2 113.1(4) . . . . ?
N1 C10 C1 O1 -64.0(4) . . . . ?
C11 C10 C1 O1 -179.5(3) . . . . ?
N1 C10 C1 C5 172.7(3) . . . . ?
C11 C10 C1 C5 57.2(4) . . . . ?
N1 C10 C1 C2 59.5(4) . . . . ?
C11 C10 C1 C2 -56.0(4) . . . . ?
C11 N2 C12 C17 -82.6(6) . . . . ?
C18 N2 C12 C17 85.3(5) . . . . ?
C11 N2 C12 C13 98.6(5) . . . . ?
C18 N2 C12 C13 -93.4(5) . . . . ?
O1 C1 C2 O2 41.9(6) . . . . ?
C5 C1 C2 O2 164.2(4) . . . . ?
C10 C1 C2 O2 -77.3(5) . . . . ?
O1 C1 C2 C3 -135.8(4) . . . . ?
C5 C1 C2 C3 -13.5(4) . . . . ?
C10 C1 C2 C3 105.0(4) . . . . ?
C10 N1 C18 N2 0.6(5) . . . . ?
C19 N1 C18 N2 167.4(4) . . . . ?
C10 N1 C18 S1 -177.5(3) . . . . ?
C19 N1 C18 S1 -10.7(6) . . . . ?
C11 N2 C18 N1 -6.8(5) . . . . ?
C12 N2 C18 N1 -176.1(4) . . . . ?
C11 N2 C18 S1 171.4(3) . . . . ?
C12 N2 C18 S1 2.1(6) . . . . ?
O1 C1 C5 O3 -41.3(5) . . . . ?
C10 C1 C5 O3 77.8(5) . . . . ?
C2 C1 C5 O3 -163.7(4) . . . . ?
O1 C1 C5 C4 136.6(4) . . . . ?
C10 C1 C5 C4 -104.3(4) . . . . ?
C2 C1 C5 C4 14.2(4) . . . . ?
O3 C5 C4 C6 -8.5(8) . . . . ?
C1 C5 C4 C6 173.7(5) . . . . ?
O3 C5 C4 C3 167.8(4) . . . . ?
C1 C5 C4 C3 -10.0(5) . . . . ?
C6 C4 C3 C9 -1.0(7) . . . . ?
C5 C4 C3 C9 -177.6(4) . . . . ?
C6 C4 C3 C2 177.6(4) . . . . ?
C5 C4 C3 C2 1.0(5) . . . . ?
O2 C2 C3 C4 -169.3(5) . . . . ?
C1 C2 C3 C4 8.3(5) . . . . ?
O2 C2 C3 C9 9.2(8) . . . . ?
C1 C2 C3 C9 -173.2(4) . . . . ?
C13 C12 C17 C16 -0.9(8) . . . . ?
N2 C12 C17 C16 -179.6(5) . . . . ?
C4 C3 C9 C8 0.6(7) . . . . ?
C2 C3 C9 C8 -177.7(5) . . . . ?
C17 C12 C13 C14 0.4(8) . . . . ?
N2 C12 C13 C14 179.1(5) . . . . ?
C3 C4 C6 C7 0.4(7) . . . . ?
C5 C4 C6 C7 176.3(5) . . . . ?
C8 C7 C6 C4 0.5(9) . . . . ?
C14 C15 C16 C17 0.1(10) . . . . ?
C14 C15 C16 Cl1 -178.4(5) . . . . ?
C12 C17 C16 C15 0.6(9) . . . . ?
C12 C17 C16 Cl1 179.1(4) . . . . ?
C3 C9 C8 C7 0.3(9) . . . . ?
C6 C7 C8 C9 -0.9(10) . . . . ?
C16 C15 C14 C13 -0.7(10) . . . . ?
C12 C13 C14 C15 0.4(9) . . . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.041



