# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_OS-Bn
_audit_block_doi                 10.5517/ccdc.csd.cc1zln4c
_database_code_depnum_ccdc_archive 'CCDC 1835173'
_audit_update_record             
;
2018-04-06 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H14 N2 O2 S4'
_chemical_formula_moiety         'C20 H14 N2 O2 S4'
_chemical_formula_weight         442.58
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   18.054(15)
_cell_length_b                   4.977(5)
_cell_length_c                   11.429(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.13(4)
_cell_angle_gamma                90.0000
_cell_volume                     976.0(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      15.10
_cell_measurement_theta_max      17.38
_cell_measurement_temperature    298
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.740
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456.00
_exptl_absorpt_coefficient_mu    0.506
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_T_max  0.970

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      298
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_reflns_number            3588
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_full        30.01
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -5.474

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2830
_reflns_number_gt                1494
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1652
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2830
_refine_ls_number_parameters     127
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0680P)²+0.1170P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.330
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.06222(4) 0.79368(18) 0.07849(7) 0.0472(3) Uani 1.0 4 d . . .
S2 S -0.01625(7) 1.1536(2) 0.29248(9) 0.0708(4) Uani 1.0 4 d . . .
O1 O 0.14076(12) 0.4893(6) 0.14454(18) 0.0594(7) Uani 1.0 4 d . . .
N1 N 0.07867(14) 0.8049(6) 0.2284(2) 0.0448(6) Uani 1.0 4 d . . .
C1 C 0.00595(15) 0.5844(6) 0.0480(3) 0.0389(7) Uani 1.0 4 d . . .
C2 C 0.00719(18) 0.9232(7) 0.2100(3) 0.0465(7) Uani 1.0 4 d . . .
C3 C 0.08270(17) 0.6124(7) 0.1427(3) 0.0438(7) Uani 1.0 4 d . . .
C4 C 0.14922(18) 0.8741(8) 0.3320(3) 0.0536(9) Uani 1.0 4 d . . .
C5 C 0.16887(18) 0.6628(7) 0.4308(3) 0.0479(8) Uani 1.0 4 d . . .
C6 C 0.23746(19) 0.5200(8) 0.4556(3) 0.0622(10) Uani 1.0 4 d . . .
C7 C 0.2572(3) 0.3296(9) 0.5482(4) 0.0732(11) Uani 1.0 4 d . . .
C8 C 0.2083(3) 0.2800(9) 0.6167(4) 0.0711(11) Uani 1.0 4 d . . .
C9 C 0.1401(3) 0.4195(9) 0.5921(4) 0.0715(11) Uani 1.0 4 d . . .
C10 C 0.1208(2) 0.6126(8) 0.5011(3) 0.0600(9) Uani 1.0 4 d . . .
H4A H 0.1408 1.0441 0.3674 0.0643 Uiso 1.0 4 calc R . .
H4B H 0.1930 0.8962 0.3007 0.0643 Uiso 1.0 4 calc R . .
H6 H 0.2708 0.5523 0.4095 0.0746 Uiso 1.0 4 calc R . .
H7 H 0.3037 0.2349 0.5642 0.0878 Uiso 1.0 4 calc R . .
H8 H 0.2215 0.1524 0.6792 0.0854 Uiso 1.0 4 calc R . .
H9 H 0.1063 0.3841 0.6373 0.0858 Uiso 1.0 4 calc R . .
H10 H 0.0748 0.7097 0.4870 0.0719 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        WinAFC
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'


#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 C1 1.729(4) yes . .
S1 C2 1.753(3) yes . .
S2 C2 1.622(4) yes . .
O1 C3 1.209(4) yes . .
N1 C2 1.374(5) yes . .
N1 C3 1.388(4) yes . .
N1 C4 1.485(4) yes . .
C1 C1 1.345(4) yes . 3_565
C1 C3 1.476(4) yes . .
C4 C5 1.503(5) yes . .
C5 C6 1.378(5) yes . .
C5 C10 1.377(6) yes . .
C6 C7 1.383(6) yes . .
C7 C8 1.372(7) yes . .
C8 C9 1.365(7) yes . .
C9 C10 1.379(6) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 S1 C2 91.75(15) yes . . .
C2 N1 C3 116.1(3) yes . . .
C2 N1 C4 123.7(3) yes . . .
C3 N1 C4 120.2(3) yes . . .
S1 C1 C1 126.7(2) yes . . 3_565
S1 C1 C3 111.1(3) yes . . .
C1 C1 C3 122.2(3) yes 3_565 . .
S1 C2 S2 120.8(2) yes . . .
S1 C2 N1 111.1(3) yes . . .
S2 C2 N1 128.0(3) yes . . .
O1 C3 N1 125.0(3) yes . . .
O1 C3 C1 125.2(3) yes . . .
N1 C3 C1 109.8(3) yes . . .
N1 C4 C5 112.4(3) yes . . .
C4 C5 C6 120.1(4) yes . . .
C4 C5 C10 121.4(3) yes . . .
C6 C5 C10 118.4(3) yes . . .
C5 C6 C7 120.8(4) yes . . .
C6 C7 C8 120.1(4) yes . . .
C7 C8 C9 119.4(4) yes . . .
C8 C9 C10 120.7(5) yes . . .
C5 C10 C9 120.6(4) yes . . .
####################################################################### 
# 
# 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_SS-Bn
_audit_block_doi                 10.5517/ccdc.csd.cc1zln5d
_database_code_depnum_ccdc_archive 'CCDC 1835174'
_audit_update_record             
;
2018-04-06 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H14 N2 S6'
_chemical_formula_moiety         'C20 H14 N2 S6'
_chemical_formula_weight         474.70
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.9840(3)
_cell_length_b                   4.79313(10)
_cell_length_c                   18.2901(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 104.4657(11)
_cell_angle_gamma                90.0000
_cell_volume                     1017.29(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6736
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    271
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488.00
_exptl_absorpt_coefficient_mu    6.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_T_max  0.882

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      271
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            10789
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_theta_max         68.19
_diffrn_reflns_theta_full        68.19
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1860
_reflns_number_gt                1389
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1389
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1860
_refine_ls_number_parameters     127
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0547P)²+1.1667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.410
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.86577(8) 0.2788(2) 0.43313(5) 0.0445(3) Uani 1.0 4 d . . .
S2 S 0.99966(9) 0.0096(3) 0.65866(5) 0.0566(4) Uani 1.0 4 d . . .
S3 S 0.68914(9) 0.6465(3) 0.46834(6) 0.0586(4) Uani 1.0 4 d . . .
N1 N 0.8385(3) 0.3230(7) 0.56863(16) 0.0406(8) Uani 1.0 4 d . . .
C1 C 0.9568(3) 0.0868(8) 0.50433(19) 0.0388(8) Uani 1.0 4 d . . .
C2 C 0.9306(3) 0.1401(8) 0.5776(2) 0.0413(9) Uani 1.0 4 d . . .
C3 C 0.7939(3) 0.4239(8) 0.4964(2) 0.0423(9) Uani 1.0 4 d . . .
C4 C 0.7923(3) 0.4075(9) 0.63358(19) 0.0441(9) Uani 1.0 4 d . . .
C5 C 0.7171(3) 0.1870(8) 0.6556(2) 0.0424(9) Uani 1.0 4 d . . .
C6 C 0.6123(4) 0.1166(9) 0.6076(3) 0.0506(10) Uani 1.0 4 d . . .
C7 C 0.5428(4) -0.0817(11) 0.6288(3) 0.0623(12) Uani 1.0 4 d . . .
C8 C 0.5760(4) -0.2104(10) 0.6985(3) 0.0616(12) Uani 1.0 4 d . . .
C9 C 0.6798(5) -0.1375(10) 0.7469(3) 0.0627(12) Uani 1.0 4 d . . .
C10 C 0.7499(4) 0.0593(10) 0.7258(2) 0.0532(11) Uani 1.0 4 d . . .
H4A H 0.7479 0.5776 0.6207 0.0529 Uiso 1.0 4 calc R . .
H4B H 0.8562 0.4475 0.6766 0.0529 Uiso 1.0 4 calc R . .
H6 H 0.5884 0.2032 0.5608 0.0608 Uiso 1.0 4 calc R . .
H7 H 0.4729 -0.1291 0.5958 0.0747 Uiso 1.0 4 calc R . .
H8 H 0.5291 -0.3439 0.7126 0.0739 Uiso 1.0 4 calc R . .
H9 H 0.7028 -0.2217 0.7941 0.0752 Uiso 1.0 4 calc R . .
H10 H 0.8196 0.1068 0.7590 0.0638 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 C1 1.739(4) yes . .
S1 C3 1.750(5) yes . .
S2 C2 1.631(4) yes . .
S3 C3 1.629(4) yes . .
N1 C2 1.387(5) yes . .
N1 C3 1.383(5) yes . .
N1 C4 1.487(5) yes . .
C1 C1 1.368(6) yes . 3_756
C1 C2 1.473(6) yes . .
C4 C5 1.507(6) yes . .
C5 C6 1.382(5) yes . .
C5 C10 1.388(6) yes . .
C6 C7 1.381(7) yes . .
C7 C8 1.383(7) yes . .
C8 C9 1.379(6) yes . .
C9 C10 1.380(7) yes . .
C4 H4A 0.970 no . .
C4 H4B 0.970 no . .
C6 H6 0.930 no . .
C7 H7 0.930 no . .
C8 H8 0.930 no . .
C9 H9 0.930 no . .
C10 H10 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 S1 C3 92.03(18) yes . . .
C2 N1 C3 116.2(4) yes . . .
C2 N1 C4 121.5(3) yes . . .
C3 N1 C4 122.4(3) yes . . .
S1 C1 C1 125.9(3) yes . . 3_756
S1 C1 C2 110.7(3) yes . . .
C1 C1 C2 123.4(3) yes 3_756 . .
S2 C2 N1 123.9(3) yes . . .
S2 C2 C1 125.8(3) yes . . .
N1 C2 C1 110.2(3) yes . . .
S1 C3 S3 121.3(3) yes . . .
S1 C3 N1 110.8(3) yes . . .
S3 C3 N1 127.9(4) yes . . .
N1 C4 C5 112.9(4) yes . . .
C4 C5 C6 120.7(4) yes . . .
C4 C5 C10 120.4(3) yes . . .
C6 C5 C10 118.8(4) yes . . .
C5 C6 C7 120.4(4) yes . . .
C6 C7 C8 120.7(4) yes . . .
C7 C8 C9 118.9(5) yes . . .
C8 C9 C10 120.6(4) yes . . .
C5 C10 C9 120.6(4) yes . . .
N1 C4 H4A 109.010 no . . .
N1 C4 H4B 108.999 no . . .
C5 C4 H4A 109.009 no . . .
C5 C4 H4B 109.004 no . . .
H4A C4 H4B 107.789 no . . .
C5 C6 H6 119.789 no . . .
C7 C6 H6 119.796 no . . .
C6 C7 H7 119.637 no . . .
C8 C7 H7 119.640 no . . .
C7 C8 H8 120.529 no . . .
C9 C8 H8 120.544 no . . .
C8 C9 H9 119.720 no . . .
C10 C9 H9 119.720 no . . .
C5 C10 H10 119.722 no . . .
C9 C10 H10 119.721 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 S1 C3 S3 179.3(3) no . . . .
C1 S1 C3 N1 -0.8(3) no . . . .
C3 S1 C1 C1 -179.1(3) no . . . 3_756
C3 S1 C1 C2 -0.5(3) no . . . .
C2 N1 C3 S1 2.0(4) no . . . .
C2 N1 C3 S3 -178.1(3) no . . . .
C3 N1 C2 S2 176.9(3) no . . . .
C3 N1 C2 C1 -2.3(4) no . . . .
C2 N1 C4 C5 -77.8(4) no . . . .
C4 N1 C2 S2 -2.2(5) no . . . .
C4 N1 C2 C1 178.6(3) no . . . .
C3 N1 C4 C5 103.2(4) no . . . .
C4 N1 C3 S1 -178.9(3) no . . . .
C4 N1 C3 S3 1.0(6) no . . . .
S1 C1 C1 S1 180(2) no . . 3_756 3_756
S1 C1 C1 C2 -1.5(6) no . . 3_756 3_756
S1 C1 C2 S2 -177.6(3) no . . . .
S1 C1 C2 N1 1.6(4) no . . . .
C1 C1 C2 S2 1.1(6) no 3_756 . . .
C1 C1 C2 N1 -179.7(3) no 3_756 . . .
C2 C1 C1 S1 1.5(6) no . . 3_756 3_756
C2 C1 C1 C2 -180(4) no . . 3_756 3_756
N1 C4 C5 C6 -66.8(5) no . . . .
N1 C4 C5 C10 115.9(4) no . . . .
C4 C5 C6 C7 -178.7(4) no . . . .
C4 C5 C10 C9 178.3(4) no . . . .
C6 C5 C10 C9 1.0(6) no . . . .
C10 C5 C6 C7 -1.4(6) no . . . .
C5 C6 C7 C8 0.9(7) no . . . .
C6 C7 C8 C9 0.0(7) no . . . .
C7 C8 C9 C10 -0.4(8) no . . . .
C8 C9 C10 C5 -0.1(7) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 S2 2.9465(16) no . 3_756
S1 C2 3.204(4) no . 3_756
S2 C1 3.186(4) no . 3_756
S2 C4 3.075(4) no . .
S2 C5 3.478(4) no . .
S2 C10 3.516(5) no . .
S3 C4 3.179(4) no . .
N1 C6 3.131(6) no . .
N1 C10 3.538(6) no . .
C2 C5 3.233(6) no . .
C3 C5 3.457(6) no . .
C5 C8 2.787(7) no . .
C6 C9 2.756(6) no . .
C7 C10 2.750(6) no . .
S3 C7 3.573(5) no . 3_666
C4 C9 3.502(7) no . 1_565
C5 C8 3.533(7) no . 1_565
C7 S3 3.573(5) no . 3_666
C8 C5 3.533(7) no . 1_545
C9 C4 3.502(7) no . 1_545
S2 H4B 2.7841 no . .
S2 H10 3.1958 no . .
S3 H4A 2.7180 no . .
S3 H6 3.1386 no . .
N1 H6 3.0197 no . .
C2 H4A 3.2673 no . .
C2 H4B 2.6552 no . .
C3 H4A 2.5764 no . .
C3 H4B 3.1939 no . .
C3 H6 3.1651 no . .
C4 H6 2.6598 no . .
C4 H10 2.6584 no . .
C5 H7 3.2333 no . .
C5 H9 3.2403 no . .
C6 H4A 2.7175 no . .
C6 H4B 3.2876 no . .
C6 H8 3.2422 no . .
C6 H10 3.2252 no . .
C7 H9 3.2205 no . .
C8 H6 3.2382 no . .
C8 H10 3.2320 no . .
C9 H7 3.2194 no . .
C10 H4A 3.1377 no . .
C10 H4B 2.5432 no . .
C10 H6 3.2264 no . .
C10 H8 3.2370 no . .
H4A H6 2.6502 no . .
H4A H10 3.3377 no . .
H4B H6 3.5718 no . .
H4B H10 2.3360 no . .
H6 H7 2.3028 no . .
H7 H8 2.3158 no . .
H8 H9 2.3129 no . .
H9 H10 2.3024 no . .
S1 H9 3.5082 no . 4_554
S1 H10 3.1425 no . 4_554
S2 H4A 3.5817 no . 1_545
S2 H4B 3.2563 no . 1_545
S2 H4B 3.0906 no . 2_746
S2 H10 3.0094 no . 2_746
S3 H6 3.5297 no . 1_565
S3 H6 3.3138 no . 3_666
S3 H7 3.1872 no . 3_656
S3 H7 3.0597 no . 3_666
S3 H9 3.2523 no . 4_554
C3 H7 3.5171 no . 3_656
C5 H4A 3.0323 no . 1_545
C5 H8 3.5206 no . 1_565
C6 H4A 3.0295 no . 1_545
C6 H8 3.5108 no . 1_565
C7 H4A 2.9849 no . 1_545
C7 H6 3.4802 no . 3_656
C7 H8 3.4213 no . 2_656
C8 H4A 2.9612 no . 1_545
C8 H8 2.8867 no . 2_656
C9 H4A 2.9664 no . 1_545
C9 H4B 3.3816 no . 1_545
C9 H8 3.1179 no . 2_656
C10 H4A 3.0013 no . 1_545
C10 H4B 3.4069 no . 1_545
H4A S2 3.5817 no . 1_565
H4A C5 3.0323 no . 1_565
H4A C6 3.0295 no . 1_565
H4A C7 2.9849 no . 1_565
H4A C8 2.9612 no . 1_565
H4A C9 2.9664 no . 1_565
H4A C10 3.0013 no . 1_565
H4A H6 3.5775 no . 1_565
H4A H7 3.5054 no . 1_565
H4A H8 3.4710 no . 1_565
H4A H9 3.4830 no . 1_565
H4A H10 3.5335 no . 1_565
H4B S2 3.2563 no . 1_565
H4B S2 3.0906 no . 2_756
H4B C9 3.3816 no . 1_565
H4B C10 3.4069 no . 1_565
H4B H9 3.5331 no . 1_565
H4B H10 3.5746 no . 1_565
H6 S3 3.5297 no . 1_545
H6 S3 3.3138 no . 3_666
H6 C7 3.4802 no . 3_656
H6 H4A 3.5775 no . 1_545
H6 H6 3.2984 no . 3_656
H6 H7 2.7954 no . 3_656
H7 S3 3.1872 no . 3_656
H7 S3 3.0597 no . 3_666
H7 C3 3.5171 no . 3_656
H7 H4A 3.5054 no . 1_545
H7 H6 2.7954 no . 3_656
H8 C5 3.5206 no . 1_545
H8 C6 3.5108 no . 1_545
H8 C7 3.4213 no . 2_646
H8 C8 2.8867 no . 2_646
H8 C9 3.1179 no . 2_646
H8 H4A 3.4710 no . 1_545
H8 H8 2.9284 no . 2_646
H8 H8 2.9284 no . 2_656
H8 H9 3.2932 no . 2_646
H9 S1 3.5082 no . 4_555
H9 S3 3.2523 no . 4_555
H9 H4A 3.4830 no . 1_545
H9 H4B 3.5331 no . 1_545
H9 H8 3.2932 no . 2_656
H10 S1 3.1425 no . 4_555
H10 S2 3.0094 no . 2_756
H10 H4A 3.5335 no . 1_545
H10 H4B 3.5746 no . 1_545
####################################################################### 
# 
# 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_OS-EtPh
_audit_block_doi                 10.5517/ccdc.csd.cc1zln6f
_database_code_depnum_ccdc_archive 'CCDC 1835175'
_audit_update_record             
;
2018-04-06 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H18 N2 O2 S4'
_chemical_formula_moiety         'C22 H18 N2 O2 S4'
_chemical_formula_weight         470.64
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   18.891(7)
_cell_length_b                   6.409(3)
_cell_length_c                   9.138(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.09(4)
_cell_angle_gamma                90.0000
_cell_volume                     1104.8(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      15.13
_cell_measurement_theta_max      17.40
_cell_measurement_temperature    298
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488.00
_exptl_absorpt_coefficient_mu    0.452
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_T_max  0.965

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      298
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_reflns_number            2475
_diffrn_reflns_av_R_equivalents  0.1261
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -0.965

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             1951
_reflns_number_gt                1118
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.2475
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1951
_refine_ls_number_parameters     136
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1437P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.420
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.54112(8) 1.2339(2) 0.16006(15) 0.0457(5) Uani 1.0 4 d . . .
S2 S 0.67002(9) 1.2558(3) 0.35891(17) 0.0581(6) Uani 1.0 4 d . . .
O1 O 0.5913(3) 0.7045(6) 0.0042(5) 0.0534(11) Uani 1.0 4 d . . .
N1 N 0.6340(3) 0.9391(7) 0.1770(5) 0.0430(12) Uani 1.0 4 d . . .
C1 C 0.5273(3) 1.0172(8) 0.0464(6) 0.0391(13) Uani 1.0 4 d . . .
C2 C 0.6200(3) 1.1312(9) 0.2359(6) 0.0453(14) Uani 1.0 4 d . . .
C3 C 0.5863(3) 0.8682(9) 0.0693(6) 0.0421(13) Uani 1.0 4 d . . .
C4 C 0.6973(3) 0.8124(10) 0.2257(7) 0.0501(15) Uani 1.0 4 d . . .
C5 C 0.7611(4) 0.8569(11) 0.1430(7) 0.0572(16) Uani 1.0 4 d . . .
C6 C 0.8208(3) 0.7153(11) 0.1960(7) 0.0544(16) Uani 1.0 4 d . . .
C7 C 0.8703(4) 0.7824(14) 0.3019(8) 0.078(3) Uani 1.0 4 d . . .
C8 C 0.9253(5) 0.651(3) 0.3558(10) 0.105(4) Uani 1.0 4 d . . .
C9 C 0.9301(5) 0.454(2) 0.2983(13) 0.107(4) Uani 1.0 4 d . . .
C10 C 0.8814(5) 0.3849(16) 0.1964(12) 0.097(3) Uani 1.0 4 d . . .
C11 C 0.8259(4) 0.5157(13) 0.1436(9) 0.071(2) Uani 1.0 4 d . . .
H4A H 0.7084 0.8389 0.3289 0.0601 Uiso 1.0 4 calc R . .
H4B H 0.6856 0.6657 0.2150 0.0601 Uiso 1.0 4 calc R . .
H5A H 0.7751 1.0014 0.1572 0.0687 Uiso 1.0 4 calc R . .
H5B H 0.7504 0.8346 0.0391 0.0687 Uiso 1.0 4 calc R . .
H7 H 0.8673 0.9173 0.3384 0.0940 Uiso 1.0 4 calc R . .
H8 H 0.9578 0.6973 0.4288 0.1256 Uiso 1.0 4 calc R . .
H9 H 0.9673 0.3674 0.3301 0.1281 Uiso 1.0 4 calc R . .
H10 H 0.8846 0.2496 0.1606 0.1165 Uiso 1.0 4 calc R . .
H11 H 0.7927 0.4666 0.0731 0.0850 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        WinAFC
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'


#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 C1 1.746(5) yes . .
S1 C2 1.738(6) yes . .
S2 C2 1.638(6) yes . .
O1 C3 1.213(7) yes . .
N1 C2 1.375(7) yes . .
N1 C3 1.376(7) yes . .
N1 C4 1.493(8) yes . .
C1 C1 1.318(8) yes . 3_675
C1 C3 1.474(8) yes . .
C4 C5 1.484(9) yes . .
C5 C6 1.508(9) yes . .
C6 C7 1.378(10) yes . .
C6 C11 1.371(11) yes . .
C7 C8 1.403(14) yes . .
C8 C9 1.374(19) yes . .
C9 C10 1.348(15) yes . .
C10 C11 1.407(12) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 S1 C2 91.9(3) yes . . .
C2 N1 C3 116.2(5) yes . . .
C2 N1 C4 122.6(5) yes . . .
C3 N1 C4 121.1(5) yes . . .
S1 C1 C1 127.1(5) yes . . 3_675
S1 C1 C3 110.1(4) yes . . .
C1 C1 C3 122.8(5) yes 3_675 . .
S1 C2 S2 122.7(4) yes . . .
S1 C2 N1 111.3(4) yes . . .
S2 C2 N1 126.0(5) yes . . .
O1 C3 N1 124.8(5) yes . . .
O1 C3 C1 124.7(5) yes . . .
N1 C3 C1 110.4(5) yes . . .
N1 C4 C5 113.7(5) yes . . .
C4 C5 C6 109.5(6) yes . . .
C5 C6 C7 120.4(7) yes . . .
C5 C6 C11 121.0(6) yes . . .
C7 C6 C11 118.6(7) yes . . .
C6 C7 C8 121.4(9) yes . . .
C7 C8 C9 118.6(9) yes . . .
C8 C9 C10 120.7(10) yes . . .
C9 C10 C11 120.6(10) yes . . .
C6 C11 C10 120.1(7) yes . . .
####################################################################### 
# 
# 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_SS-EtPh
_audit_block_doi                 10.5517/ccdc.csd.cc1zln7g
_database_code_depnum_ccdc_archive 'CCDC 1835176'
_audit_update_record             
;
2018-04-06 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H18 N2 S6'
_chemical_formula_moiety         'C22 H18 N2 S6'
_chemical_formula_weight         502.76
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_Int_Tables_number      56
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,+Y,1/2+Z
3 +X,1/2-Y,1/2+Z
4 1/2-X,1/2-Y,+Z
5 -X,-Y,-Z
6 1/2+X,-Y,1/2-Z
7 -X,1/2+Y,1/2-Z
8 1/2+X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   23.6666(4)
_cell_length_b                   13.6498(2)
_cell_length_c                   7.17290(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2317.17(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21726
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    271
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.037
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040.00
_exptl_absorpt_coefficient_mu    5.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_T_max  0.814

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      271
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            24371
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_theta_max         68.20
_diffrn_reflns_theta_full        68.20
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2131
_reflns_number_gt                1953
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0930
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2131
_refine_ls_number_parameters     136
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0562P)²+0.4053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.046844(17) 0.36320(3) 0.44101(6) 0.04550(15) Uani 1.0 8 d . . .
S2 S 0.033410(19) 0.65590(4) 0.24745(7) 0.05773(18) Uani 1.0 8 d . . .
S3 S 0.13914(3) 0.31090(4) 0.17927(8) 0.0728(2) Uani 1.0 8 d . . .
N1 N 0.08953(5) 0.48744(10) 0.20837(18) 0.0427(4) Uani 1.0 8 d . . .
C1 C 0.02041(6) 0.48298(11) 0.4414(2) 0.0371(4) Uani 1.0 8 d . . .
C2 C 0.04878(6) 0.54168(12) 0.2982(2) 0.0403(4) Uani 1.0 8 d . . .
C3 C 0.09496(7) 0.39125(13) 0.2624(3) 0.0476(4) Uani 1.0 8 d . . .
C4 C 0.12511(7) 0.52836(14) 0.0587(2) 0.0486(5) Uani 1.0 8 d . . .
C5 C 0.09759(8) 0.51461(18) -0.1321(3) 0.0620(6) Uani 1.0 8 d . . .
C6 C 0.13798(6) 0.54306(14) -0.2850(2) 0.0442(4) Uani 1.0 8 d . . .
C7 C 0.17355(8) 0.47393(14) -0.3644(3) 0.0528(5) Uani 1.0 8 d . . .
C8 C 0.21175(8) 0.49968(16) -0.5009(3) 0.0615(5) Uani 1.0 8 d . . .
C9 C 0.21554(8) 0.59466(17) -0.5602(3) 0.0619(6) Uani 1.0 8 d . . .
C10 C 0.18083(9) 0.66388(16) -0.4832(3) 0.0642(6) Uani 1.0 8 d . . .
C11 C 0.14195(8) 0.63846(15) -0.3473(3) 0.0546(5) Uani 1.0 8 d . . .
H4A H 0.1616 0.4962 0.0599 0.0583 Uiso 1.0 8 calc R . .
H4B H 0.1311 0.5976 0.0813 0.0583 Uiso 1.0 8 calc R . .
H5A H 0.0865 0.4467 -0.1476 0.0744 Uiso 1.0 8 calc R . .
H5B H 0.0638 0.5547 -0.1401 0.0744 Uiso 1.0 8 calc R . .
H7 H 0.1716 0.4091 -0.3248 0.0634 Uiso 1.0 8 calc R . .
H8 H 0.2351 0.4522 -0.5529 0.0738 Uiso 1.0 8 calc R . .
H9 H 0.2415 0.6120 -0.6519 0.0743 Uiso 1.0 8 calc R . .
H10 H 0.1834 0.7287 -0.5225 0.0770 Uiso 1.0 8 calc R . .
H11 H 0.1183 0.6862 -0.2976 0.0655 Uiso 1.0 8 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
S1 C1 1.7506(16) yes . .
S1 C3 1.7561(18) yes . .
S2 C2 1.6419(17) yes . .
S3 C3 1.6285(19) yes . .
N1 C2 1.376(2) yes . .
N1 C3 1.375(3) yes . .
N1 C4 1.474(2) yes . .
C1 C1 1.362(2) yes . 5_566
C1 C2 1.465(2) yes . .
C4 C5 1.528(3) yes . .
C5 C6 1.506(3) yes . .
C6 C7 1.387(3) yes . .
C6 C11 1.380(3) yes . .
C7 C8 1.378(3) yes . .
C8 C9 1.367(4) yes . .
C9 C10 1.368(3) yes . .
C10 C11 1.385(3) yes . .
C4 H4A 0.970 no . .
C4 H4B 0.970 no . .
C5 H5A 0.970 no . .
C5 H5B 0.970 no . .
C7 H7 0.930 no . .
C8 H8 0.930 no . .
C9 H9 0.930 no . .
C10 H10 0.930 no . .
C11 H11 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 S1 C3 91.68(8) yes . . .
C2 N1 C3 116.56(14) yes . . .
C2 N1 C4 122.51(14) yes . . .
C3 N1 C4 120.92(14) yes . . .
S1 C1 C1 124.95(12) yes . . 5_566
S1 C1 C2 110.23(11) yes . . .
C1 C1 C2 124.81(14) yes 5_566 . .
S2 C2 N1 124.21(12) yes . . .
S2 C2 C1 124.97(12) yes . . .
N1 C2 C1 110.80(14) yes . . .
S1 C3 S3 122.46(11) yes . . .
S1 C3 N1 110.69(12) yes . . .
S3 C3 N1 126.85(13) yes . . .
N1 C4 C5 111.25(14) yes . . .
C4 C5 C6 110.51(15) yes . . .
C5 C6 C7 120.58(18) yes . . .
C5 C6 C11 121.50(17) yes . . .
C7 C6 C11 117.90(16) yes . . .
C6 C7 C8 121.08(18) yes . . .
C7 C8 C9 120.39(19) yes . . .
C8 C9 C10 119.32(19) yes . . .
C9 C10 C11 120.7(2) yes . . .
C6 C11 C10 120.64(18) yes . . .
N1 C4 H4A 109.378 no . . .
N1 C4 H4B 109.375 no . . .
C5 C4 H4A 109.381 no . . .
C5 C4 H4B 109.380 no . . .
H4A C4 H4B 108.017 no . . .
C4 C5 H5A 109.552 no . . .
C4 C5 H5B 109.542 no . . .
C6 C5 H5A 109.551 no . . .
C6 C5 H5B 109.545 no . . .
H5A C5 H5B 108.097 no . . .
C6 C7 H7 119.452 no . . .
C8 C7 H7 119.471 no . . .
C7 C8 H8 119.805 no . . .
C9 C8 H8 119.804 no . . .
C8 C9 H9 120.343 no . . .
C10 C9 H9 120.341 no . . .
C9 C10 H10 119.670 no . . .
C11 C10 H10 119.664 no . . .
C6 C11 H11 119.681 no . . .
C10 C11 H11 119.676 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 S1 C3 S3 179.16(12) no . . . .
C1 S1 C3 N1 -0.52(11) no . . . .
C3 S1 C1 C1 -178.10(12) no . . . 5_566
C3 S1 C1 C2 1.51(10) no . . . .
C2 N1 C3 S1 -0.71(18) no . . . .
C2 N1 C3 S3 179.62(13) no . . . .
C3 N1 C2 S2 -176.84(12) no . . . .
C3 N1 C2 C1 1.87(18) no . . . .
C2 N1 C4 C5 -89.44(17) no . . . .
C4 N1 C2 S2 1.9(2) no . . . .
C4 N1 C2 C1 -179.42(12) no . . . .
C3 N1 C4 C5 89.22(17) no . . . .
C4 N1 C3 S1 -179.44(11) no . . . .
C4 N1 C3 S3 0.9(3) no . . . .
S1 C1 C1 S1 -179.97(14) no . . 5_566 5_566
S1 C1 C1 C2 -0.4(2) no . . 5_566 5_566
S1 C1 C2 S2 176.54(9) no . . . .
S1 C1 C2 N1 -2.15(15) no . . . .
C1 C1 C2 S2 -3.8(3) no 5_566 . . .
C1 C1 C2 N1 177.46(13) no 5_566 . . .
C2 C1 C1 S1 0.4(3) no . . 5_566 5_566
C2 C1 C1 C2 180(14) no . . 5_566 5_566
N1 C4 C5 C6 -171.65(14) no . . . .
C4 C5 C6 C7 91.0(2) no . . . .
C4 C5 C6 C11 -87.29(19) no . . . .
C5 C6 C7 C8 -178.23(14) no . . . .
C5 C6 C11 C10 177.57(14) no . . . .
C7 C6 C11 C10 -0.8(3) no . . . .
C11 C6 C7 C8 0.1(3) no . . . .
C6 C7 C8 C9 0.4(3) no . . . .
C7 C8 C9 C10 -0.3(3) no . . . .
C8 C9 C10 C11 -0.4(3) no . . . .
C9 C10 C11 C6 0.9(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
S1 S2 2.9443(7) no . 5_566
S1 C2 3.2103(16) no . 5_566
S2 C1 3.1934(16) no . 5_566
S2 C4 3.0940(18) no . .
S3 C4 3.109(2) no . .
C2 C5 3.317(3) no . .
C3 C5 3.294(3) no . .
C4 C7 3.328(3) no . .
C4 C11 3.302(3) no . .
C6 C9 2.786(3) no . .
C7 C10 2.735(3) no . .
C8 C11 2.744(3) no . .
N1 C8 3.570(3) no . 1_556
C1 C5 3.589(3) no . 1_556
C1 C5 3.567(3) no . 5_565
C1 C6 3.502(2) no . 1_556
C3 C7 3.449(3) no . 1_556
C3 C8 3.565(3) no . 1_556
C4 C9 3.587(3) no . 1_556
C5 C1 3.589(3) no . 1_554
C5 C1 3.567(3) no . 5_565
C6 C1 3.502(2) no . 1_554
C7 C3 3.449(3) no . 1_554
C8 N1 3.570(3) no . 1_554
C8 C3 3.565(3) no . 1_554
C9 C4 3.587(3) no . 1_554
S2 H4B 2.7203 no . .
S2 H5B 3.1864 no . .
S3 H4A 2.7229 no . .
S3 H5A 3.2372 no . .
N1 H5A 2.6140 no . .
N1 H5B 2.7313 no . .
C2 H4A 3.2318 no . .
C2 H4B 2.6080 no . .
C2 H5A 3.5645 no . .
C2 H5B 3.1691 no . .
C3 H4A 2.5796 no . .
C3 H4B 3.2182 no . .
C3 H5A 3.0431 no . .
C4 H7 3.3805 no . .
C4 H11 3.3462 no . .
C5 H7 2.6552 no . .
C5 H11 2.6703 no . .
C6 H4A 2.6159 no . .
C6 H4B 2.7361 no . .
C6 H8 3.2424 no . .
C6 H10 3.2364 no . .
C7 H4A 3.0710 no . .
C7 H5A 2.6072 no . .
C7 H5B 3.2475 no . .
C7 H9 3.2235 no . .
C7 H11 3.2143 no . .
C8 H10 3.2005 no . .
C9 H7 3.2164 no . .
C9 H11 3.2260 no . .
C10 H8 3.2015 no . .
C11 H4A 3.5383 no . .
C11 H4B 3.1352 no . .
C11 H5A 3.2599 no . .
C11 H5B 2.6335 no . .
C11 H7 3.2119 no . .
C11 H9 3.2324 no . .
H4A H5A 2.4146 no . .
H4A H5B 2.8380 no . .
H4A H7 3.0134 no . .
H4B H5A 2.8382 no . .
H4B H5B 2.3241 no . .
H4B H11 2.9895 no . .
H5A H7 2.4352 no . .
H5A H11 3.5225 no . .
H5B H7 3.4939 no . .
H5B H11 2.4811 no . .
H7 H8 2.2981 no . .
H8 H9 2.2996 no . .
H9 H10 2.2986 no . .
H10 H11 2.3053 no . .
S1 H5A 3.2999 no . 1_556
S1 H5B 3.5743 no . 5_565
S1 H7 3.4541 no . 1_556
S2 H5A 3.2453 no . 5_565
S2 H11 2.9643 no . 3_565
S3 H7 3.1003 no . 3_555
S3 H8 3.5448 no . 1_556
C1 H5A 3.3747 no . 1_556
C1 H5A 3.4309 no . 5_565
C1 H5B 3.3207 no . 1_556
C1 H5B 2.9850 no . 5_565
C2 H5A 3.3838 no . 5_565
C2 H5B 3.1812 no . 5_565
C3 H7 3.4805 no . 1_556
C4 H8 3.5595 no . 2_555
C6 H9 3.1529 no . 2_555
C7 H8 3.1230 no . 2_555
C7 H9 3.1500 no . 2_555
C8 H4A 3.3669 no . 1_554
C8 H4A 3.0281 no . 2_554
C8 H8 3.5110 no . 2_555
C8 H9 3.1375 no . 2_555
C9 H4A 3.2955 no . 1_554
C9 H4A 3.3160 no . 2_554
C9 H4B 3.2566 no . 1_554
C9 H9 3.1095 no . 2_555
C9 H10 3.4077 no . 4_565
C10 H4B 3.4582 no . 1_554
C10 H4B 3.4921 no . 3_564
C10 H9 3.0871 no . 2_555
C10 H10 3.5439 no . 4_565
C10 H11 3.3862 no . 3_564
C11 H9 3.1160 no . 2_555
C11 H10 3.1112 no . 3_565
H4A C8 3.3669 no . 1_556
H4A C8 3.0281 no . 2_555
H4A C9 3.2955 no . 1_556
H4A C9 3.3160 no . 2_555
H4A H8 3.3310 no . 1_556
H4A H8 2.6434 no . 2_555
H4A H9 3.2158 no . 1_556
H4A H9 3.1729 no . 2_555
H4B C9 3.2566 no . 1_556
H4B C10 3.4582 no . 1_556
H4B C10 3.4921 no . 3_565
H4B H9 3.2432 no . 1_556
H4B H9 3.4544 no . 2_555
H4B H10 3.5780 no . 1_556
H4B H10 2.7761 no . 3_565
H4B H11 3.0914 no . 3_565
H5A S1 3.2999 no . 1_554
H5A S2 3.2453 no . 5_565
H5A C1 3.3747 no . 1_554
H5A C1 3.4309 no . 5_565
H5A C2 3.3838 no . 5_565
H5B S1 3.5743 no . 5_565
H5B C1 3.3207 no . 1_554
H5B C1 2.9850 no . 5_565
H5B C2 3.1812 no . 5_565
H7 S1 3.4541 no . 1_554
H7 S3 3.1003 no . 3_554
H7 C3 3.4805 no . 1_554
H7 H8 3.0043 no . 2_555
H8 S3 3.5448 no . 1_554
H8 C4 3.5595 no . 2_554
H8 C7 3.1230 no . 2_554
H8 C8 3.5110 no . 2_554
H8 H4A 3.3310 no . 1_554
H8 H4A 2.6434 no . 2_554
H8 H7 3.0043 no . 2_554
H9 C6 3.1529 no . 2_554
H9 C7 3.1500 no . 2_554
H9 C8 3.1375 no . 2_554
H9 C9 3.1095 no . 2_554
H9 C10 3.0871 no . 2_554
H9 C11 3.1160 no . 2_554
H9 H4A 3.2158 no . 1_554
H9 H4A 3.1729 no . 2_554
H9 H4B 3.2432 no . 1_554
H9 H4B 3.4544 no . 2_554
H9 H10 3.5728 no . 2_554
H9 H10 2.9589 no . 4_565
H10 C9 3.4077 no . 4_565
H10 C10 3.5439 no . 4_565
H10 C11 3.1112 no . 3_564
H10 H4B 3.5780 no . 1_554
H10 H4B 2.7761 no . 3_564
H10 H9 3.5728 no . 2_555
H10 H9 2.9589 no . 4_565
H10 H10 3.2068 no . 4_565
H10 H11 2.7601 no . 3_564
H11 S2 2.9643 no . 3_564
H11 C10 3.3862 no . 3_565
H11 H4B 3.0914 no . 3_564
H11 H10 2.7601 no . 3_565
