# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1_sq
_database_code_depnum_ccdc_archive 'CCDC 1818775'
_audit_update_record             
;
2018-01-21 deposited with the CCDC.
2018-03-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C45 H32 N4 S4'
_chemical_formula_sum            'C45 H32 N4 S4'
_chemical_formula_weight         756.98

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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+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                   22.728(6)
_cell_length_b                   7.4934(18)
_cell_length_c                   21.408(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.113(11)
_cell_angle_gamma                90
_cell_volume                     3646.0(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2307
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      24.99

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             1576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.301
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6308
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON100 CMOS detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11991
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_av_R_equivalents  0.1055
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.617
_diffrn_reflns_theta_max         24.490
_diffrn_reflns_theta_full        24.490
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3009
_reflns_number_gt                1799
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0986P)²+4.9670P] 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         3009
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1432
_refine_ls_R_factor_gt           0.0811
_refine_ls_wR_factor_ref         0.2266
_refine_ls_wR_factor_gt          0.1947
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.168
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5000 1.0678(10) 0.7500 0.0269(17) Uani 1 2 d S T P . .
C2 C 0.4794(2) 0.9442(7) 0.8014(2) 0.0258(12) Uani 1 1 d . . . . .
C3 C 0.5175(3) 0.8182(7) 0.8244(3) 0.0314(13) Uani 1 1 d . . . . .
H3 H 0.5564 0.8141 0.8085 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5017(3) 0.7001(7) 0.8688(3) 0.0326(13) Uani 1 1 d . . . . .
H4 H 0.5296 0.6169 0.8844 0.039 Uiso 1 1 calc R U . . .
C5 C 0.4457(3) 0.6998(7) 0.8915(2) 0.0292(13) Uani 1 1 d . . . . .
C6 C 0.4074(3) 0.8247(7) 0.8700(3) 0.0335(14) Uani 1 1 d . . . . .
H6 H 0.3685 0.8284 0.8862 0.040 Uiso 1 1 calc R U . . .
C7 C 0.4239(3) 0.9454(7) 0.8253(3) 0.0320(14) Uani 1 1 d . . . . .
H7 H 0.3963 1.0311 0.8107 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4468(3) 0.4246(8) 0.9379(3) 0.0360(14) Uani 1 1 d . . . . .
H8 H 0.4801 0.3997 0.9125 0.043 Uiso 1 1 calc R U . . .
C9 C 0.4249(3) 0.2866(8) 0.9767(3) 0.0356(14) Uani 1 1 d . . . . .
C10 C 0.4410(3) 0.1181(8) 0.9763(3) 0.0414(16) Uani 1 1 d . . . . .
H10 H 0.4725 0.0736 0.9518 0.050 Uiso 1 1 calc R U . . .
C11 C 0.4072(3) 0.0114(9) 1.0157(3) 0.0470(17) Uani 1 1 d . . . . .
H11 H 0.4127 -0.1134 1.0206 0.056 Uiso 1 1 calc R U . . .
C12 C 0.3675(3) 0.1021(9) 1.0447(3) 0.0488(17) Uani 1 1 d . . . . .
H12 H 0.3410 0.0510 1.0738 0.059 Uiso 1 1 calc R U . . .
C13 C 0.5487(2) 1.1914(7) 0.7721(2) 0.0282(13) Uani 1 1 d . . . . .
C14 C 0.5695(3) 1.3165(7) 0.7309(3) 0.0373(15) Uani 1 1 d . . . . .
H14 H 0.5533 1.3213 0.6900 0.045 Uiso 1 1 calc R U . . .
C15 C 0.6126(3) 1.4341(8) 0.7469(3) 0.0394(16) Uani 1 1 d . . . . .
H15 H 0.6270 1.5165 0.7168 0.047 Uiso 1 1 calc R U . . .
C16 C 0.6352(2) 1.4335(7) 0.8059(3) 0.0302(13) Uani 1 1 d . . . . .
C17 C 0.6146(3) 1.3099(7) 0.8470(3) 0.0314(13) Uani 1 1 d . . . . .
H17 H 0.6306 1.3056 0.8879 0.038 Uiso 1 1 calc R U . . .
C18 C 0.5715(2) 1.1922(7) 0.8307(2) 0.0282(13) Uani 1 1 d . . . . .
H18 H 0.5572 1.1098 0.8607 0.034 Uiso 1 1 calc R U . . .
C19 C 0.6808(3) 1.7038(8) 0.8023(3) 0.0389(15) Uani 1 1 d . . . . .
H19 H 0.6549 1.7319 0.7689 0.047 Uiso 1 1 calc R U . . .
C20 C 0.7207(3) 1.8341(8) 0.8234(3) 0.0371(15) Uani 1 1 d . . . . .
C21 C 0.7212(3) 2.0084(8) 0.8088(3) 0.0445(16) Uani 1 1 d . . . . .
H21 H 0.6970 2.0589 0.7772 0.053 Uiso 1 1 calc R U . . .
C22 C 0.7600(3) 2.1067(9) 0.8441(3) 0.0479(18) Uani 1 1 d . . . . .
H22 H 0.7649 2.2322 0.8404 0.057 Uiso 1 1 calc R U . . .
C23 C 0.7896(3) 2.0070(9) 0.8836(4) 0.0535(19) Uani 1 1 d . . . . .
H23 H 0.8184 2.0528 0.9115 0.064 Uiso 1 1 calc R U . . .
N1 N 0.4247(2) 0.5780(6) 0.9352(2) 0.0323(12) Uani 1 1 d . . . . .
N2 N 0.6784(2) 1.5507(6) 0.8266(2) 0.0349(12) Uani 1 1 d . . . . .
S1 S 0.36743(8) 0.3199(2) 1.02567(8) 0.0485(5) Uani 1 1 d . . . . .
S2 S 0.77129(8) 1.7906(2) 0.87980(9) 0.0531(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.513(7) . ?
C1 C2 1.513(7) 2_656 ?
C1 C13 1.519(7) 2_656 ?
C1 C13 1.519(7) . ?
C2 C7 1.362(8) . ?
C2 C3 1.372(7) . ?
C3 C4 1.348(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.363(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.357(8) . ?
C5 N1 1.393(7) . ?
C6 C7 1.369(8) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.256(7) . ?
C8 C9 1.417(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.315(8) . ?
C9 S1 1.695(6) . ?
C10 C11 1.393(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.289(9) . ?
C11 H11 0.9500 . ?
C12 S1 1.682(7) . ?
C12 H12 0.9500 . ?
C13 C18 1.355(7) . ?
C13 C14 1.372(8) . ?
C14 C15 1.361(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.362(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.361(8) . ?
C16 N2 1.391(7) . ?
C17 C18 1.363(8) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 N2 1.260(7) . ?
C19 C20 1.407(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.343(8) . ?
C20 S2 1.697(6) . ?
C21 C22 1.375(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.312(9) . ?
C22 H22 0.9500 . ?
C23 S2 1.676(7) . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 104.5(6) . 2_656 ?
C2 C1 C13 111.9(3) . 2_656 ?
C2 C1 C13 111.9(3) 2_656 2_656 ?
C2 C1 C13 111.9(3) . . ?
C2 C1 C13 111.9(3) 2_656 . ?
C13 C1 C13 104.8(6) 2_656 . ?
C7 C2 C3 116.9(5) . . ?
C7 C2 C1 123.9(4) . . ?
C3 C2 C1 119.1(5) . . ?
C4 C3 C2 122.5(6) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 120.1(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 118.5(5) . . ?
C6 C5 N1 117.4(5) . . ?
C4 C5 N1 124.1(5) . . ?
C5 C6 C7 121.1(6) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 120.9(5) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N1 C8 C9 123.6(6) . . ?
N1 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?
C10 C9 C8 126.8(6) . . ?
C10 C9 S1 111.1(5) . . ?
C8 C9 S1 121.8(5) . . ?
C9 C10 C11 113.1(7) . . ?
C9 C10 H10 123.4 . . ?
C11 C10 H10 123.4 . . ?
C12 C11 C10 112.1(6) . . ?
C12 C11 H11 124.0 . . ?
C10 C11 H11 124.0 . . ?
C11 C12 S1 113.3(5) . . ?
C11 C12 H12 123.4 . . ?
S1 C12 H12 123.4 . . ?
C18 C13 C14 117.4(5) . . ?
C18 C13 C1 124.6(4) . . ?
C14 C13 C1 117.9(4) . . ?
C15 C14 C13 122.0(5) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C16 120.0(5) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 118.2(5) . . ?
C17 C16 N2 117.9(5) . . ?
C15 C16 N2 123.9(5) . . ?
C16 C17 C18 121.5(5) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C13 C18 C17 120.8(5) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
N2 C19 C20 121.8(6) . . ?
N2 C19 H19 119.1 . . ?
C20 C19 H19 119.1 . . ?
C21 C20 C19 127.3(6) . . ?
C21 C20 S2 110.3(5) . . ?
C19 C20 S2 122.0(5) . . ?
C20 C21 C22 113.5(6) . . ?
C20 C21 H21 123.2 . . ?
C22 C21 H21 123.2 . . ?
C23 C22 C21 112.1(6) . . ?
C23 C22 H22 124.0 . . ?
C21 C22 H22 124.0 . . ?
C22 C23 S2 113.2(6) . . ?
C22 C23 H23 123.4 . . ?
S2 C23 H23 123.4 . . ?
C8 N1 C5 119.6(5) . . ?
C19 N2 C16 118.3(5) . . ?
C12 S1 C9 90.4(3) . . ?
C23 S2 C20 90.9(3) . . ?

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.080



