# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1901937'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University of Rennes 
France
;
_audit_update_record             
;
2019-03-08 deposited with the CCDC.	2019-09-24 downloaded from the CCDC.
;

_audit_creation_date             2017-12-20T09:42:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            '	C22 H16 N4 S6'
_chemical_formula_moiety         'C10 H12 S6, C12 H4 N4'
_chemical_formula_weight         528.75

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8415(3)
_cell_length_b                   7.6270(7)
_cell_length_c                   18.9474(17)
_cell_angle_alpha                90.790(3)
_cell_angle_beta                 90.292(3)
_cell_angle_gamma                93.350(3)
_cell_volume                     554.13(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6683
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      27.52
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_T_max  0.994

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.6715  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------# 
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      0.057833
_diffrn_orient_matrix_ub_12      -0.090655
_diffrn_orient_matrix_ub_13      -0.036032
_diffrn_orient_matrix_ub_21      0.049959
_diffrn_orient_matrix_ub_22      0.09451
_diffrn_orient_matrix_ub_23      -0.035214
_diffrn_orient_matrix_ub_31      0.249314
_diffrn_orient_matrix_ub_32      0.01013
_diffrn_orient_matrix_ub_33      0.015741
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_number            12662
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.226
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             2519
_reflns_number_gt                2217
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²+0.6645P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2519
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0874
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.073

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0706(5) 0.4563(3) 0.52723(10) 0.0111(4) Uani 1 1 d . . . . .
C2 C 0.3290(5) 0.3715(3) 0.64737(10) 0.0103(4) Uani 1 1 d . . . . .
C3 C 0.3047(5) 0.2199(3) 0.60913(10) 0.0116(4) Uani 1 1 d . . . . .
C4 C 0.4054(6) 0.0435(3) 0.63309(11) 0.0157(4) Uani 1 1 d . . . . .
H4A H 0.5377 0.0569 0.6761 0.024 Uiso 1 1 calc R U . . .
H4B H 0.5441 -0.009 0.5974 0.024 Uiso 1 1 calc R U . . .
H4C H 0.1989 -0.0304 0.641 0.024 Uiso 1 1 calc R U . . .
C5 C 0.4311(6) 0.6106(3) 0.75810(12) 0.0190(5) Uani 1 1 d . . . . .
H5A H 0.5481 0.6887 0.7254 0.028 Uiso 1 1 calc R U . . .
H5B H 0.5223 0.634 0.8048 0.028 Uiso 1 1 calc R U . . .
H5C H 0.1858 0.6284 0.7574 0.028 Uiso 1 1 calc R U . . .
C6 C 0.5732(5) -0.1779(3) 0.99281(10) 0.0119(4) Uani 1 1 d . . . . .
H6 H 0.6232 -0.2954 0.9884 0.014 Uiso 1 1 calc R U . . .
C7 C 0.3890(5) -0.1027(3) 0.94111(10) 0.0117(4) Uani 1 1 d . . . . .
H7 H 0.314 -0.1697 0.902 0.014 Uiso 1 1 calc R U . . .
C8 C 0.3083(5) 0.0787(3) 0.94588(10) 0.0113(4) Uani 1 1 d . . . . .
C9 C 0.1169(6) 0.1553(3) 0.89276(11) 0.0124(4) Uani 1 1 d . . . . .
C10 C 0.0018(5) 0.0572(3) 0.83103(11) 0.0130(4) Uani 1 1 d . . . . .
C11 C 0.0262(5) 0.3343(3) 0.89631(10) 0.0133(4) Uani 1 1 d . . . . .
N1 N -0.0888(5) -0.0230(3) 0.78211(10) 0.0209(4) Uani 1 1 d . . . . .
N2 N -0.0516(6) 0.4780(3) 0.89935(11) 0.0227(4) Uani 1 1 d . . . . .
S1 S 0.14668(14) 0.23389(6) 0.52295(3) 0.01221(13) Uani 1 1 d . . . . .
S2 S 0.19288(14) 0.56079(6) 0.60667(3) 0.01208(13) Uani 1 1 d . . . . .
S3 S 0.50092(14) 0.38692(7) 0.73310(3) 0.01426(14) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1 1.364(4) 2_566 ?
C1 S1 1.739(2) . ?
C1 S2 1.743(2) . ?
C2 C3 1.355(3) . ?
C2 S3 1.750(2) . ?
C2 S2 1.751(2) . ?
C3 C4 1.497(3) . ?
C3 S1 1.746(2) . ?
C4 H4A 0.96 . ?
C4 H4B 0.96 . ?
C4 H4C 0.96 . ?
C5 S3 1.800(2) . ?
C5 H5A 0.96 . ?
C5 H5B 0.96 . ?
C5 H5C 0.96 . ?
C6 C7 1.358(3) . ?
C6 C8 1.435(3) 2_657 ?
C6 H6 0.93 . ?
C7 C8 1.437(3) . ?
C7 H7 0.93 . ?
C8 C9 1.398(3) . ?
C8 C6 1.435(3) 2_657 ?
C9 C11 1.429(3) . ?
C9 C10 1.434(3) . ?
C10 N1 1.145(3) . ?
C11 N2 1.153(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C1 S1 123.1(2) 2_566 . ?
C1 C1 S2 122.2(2) 2_566 . ?
S1 C1 S2 114.77(11) . . ?
C3 C2 S3 123.21(16) . . ?
C3 C2 S2 117.35(15) . . ?
S3 C2 S2 119.41(11) . . ?
C2 C3 C4 126.46(19) . . ?
C2 C3 S1 116.30(15) . . ?
C4 C3 S1 117.23(15) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
S3 C5 H5A 109.5 . . ?
S3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
S3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C8 120.94(19) . 2_657 ?
C7 C6 H6 119.5 . . ?
C8 C6 H6 119.5 2_657 . ?
C6 C7 C8 121.13(18) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C6 121.11(19) . 2_657 ?
C9 C8 C7 120.95(19) . . ?
C6 C8 C7 117.94(18) 2_657 . ?
C8 C9 C11 122.51(19) . . ?
C8 C9 C10 121.26(19) . . ?
C11 C9 C10 116.23(18) . . ?
N1 C10 C9 179.2(2) . . ?
N2 C11 C9 179.1(2) . . ?
C1 S1 C3 96.13(9) . . ?
C1 S2 C2 95.38(9) . . ?
C2 S3 C5 102.66(10) . . ?

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
S3 C2 C3 C4 2.1(3) . . . . ?
S2 C2 C3 C4 179.98(17) . . . . ?
S3 C2 C3 S1 -176.76(11) . . . . ?
S2 C2 C3 S1 1.1(2) . . . . ?
C8 C6 C7 C8 0.3(3) 2_657 . . . ?
C6 C7 C8 C9 -179.6(2) . . . . ?
C6 C7 C8 C6 -0.3(3) . . . 2_657 ?
C6 C8 C9 C11 -0.5(3) 2_657 . . . ?
C7 C8 C9 C11 178.83(19) . . . . ?
C6 C8 C9 C10 179.23(19) 2_657 . . . ?
C7 C8 C9 C10 -1.5(3) . . . . ?
C1 C1 S1 C3 -177.9(3) 2_566 . . . ?
S2 C1 S1 C3 2.65(14) . . . . ?
C2 C3 S1 C1 -2.24(19) . . . . ?
C4 C3 S1 C1 178.76(17) . . . . ?
C1 C1 S2 C2 178.4(3) 2_566 . . . ?
S1 C1 S2 C2 -2.18(14) . . . . ?
C3 C2 S2 C1 0.67(19) . . . . ?
S3 C2 S2 C1 178.60(13) . . . . ?
C3 C2 S3 C5 -175.42(19) . . . . ?
S2 C2 S3 C5 6.78(16) . . . . ?

