# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_Ligand
_database_code_depnum_ccdc_archive 'CCDC 1855729'
_audit_update_record             
;
2018-08-28 deposited with the CCDC.
2018-09-03 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         'C32 H28 N4 O2 S2'
_chemical_formula_sum            'C32 H28 N4 O2 S2'
_chemical_formula_weight         564.70

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.4376(2)
_cell_length_b                   8.0683(4)
_cell_length_c                   17.0332(9)
_cell_angle_alpha                77.328(3)
_cell_angle_beta                 84.635(3)
_cell_angle_gamma                80.612(3)
_cell_volume                     718.02(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2617
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      25.10

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             770
_exptl_transmission_factor_min   0.741
_exptl_transmission_factor_max   0.842
_exptl_crystal_size_max          0.423
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.222
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            5386
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.649
_diffrn_reflns_theta_max         25.205
_diffrn_reflns_theta_full        25.205
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             2565
_reflns_number_gt                1699
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-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)+(0.0712P)²+0.3255P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2565
_refine_ls_number_parameters     187
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1625
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.043
_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 0.65834(17) 0.40831(10) 0.36171(5) 0.0662(3) Uani 1 1 d . . . . .
N2 N 0.3468(5) 0.5929(3) 0.23675(18) 0.0740(8) Uani 1 1 d . . . . .
C16 C 0.9446(6) 0.1768(4) 0.46956(18) 0.0545(8) Uani 1 1 d . . . . .
C15 C 0.8367(6) -0.0825(4) 0.55517(19) 0.0623(8) Uani 1 1 d . . . . .
H15 H 0.724816 -0.137344 0.592688 0.075 Uiso 1 1 calc R U . . .
N1 N -0.2070(6) 0.3407(4) 0.0828(2) 0.0850(9) Uani 1 1 d . . . . .
C12 C 0.6367(5) 0.6323(4) 0.32616(17) 0.0512(7) Uani 1 1 d . . . . .
O1 O 0.7304(7) 0.0724(4) -0.0006(3) 0.1256(12) Uani 1 1 d D . . . .
H1A H 0.584(10) 0.052(17) -0.004(9) 0.188 Uiso 0.5 1 d D U P . .
H1B H 0.70(2) 0.150(12) 0.028(7) 0.188 Uiso 0.5 1 d D U P . .
C11 C 0.7723(6) 0.7377(4) 0.35416(19) 0.0606(8) Uani 1 1 d . . . . .
H11 H 0.879763 0.689949 0.395281 0.073 Uiso 1 1 calc R U . . .
C14 C 0.7829(6) 0.0918(4) 0.5247(2) 0.0635(8) Uani 1 1 d . . . . .
H14 H 0.634850 0.152692 0.541886 0.076 Uiso 1 1 calc R U . . .
C7 C 0.4743(6) 0.7063(4) 0.2654(2) 0.0619(8) Uani 1 1 d . . . . .
C13 C 0.8874(6) 0.3672(4) 0.4370(2) 0.0652(9) Uani 1 1 d . . . . .
H13A H 1.038907 0.411315 0.413043 0.078 Uiso 1 1 calc R U . . .
H13B H 0.823040 0.425156 0.480466 0.078 Uiso 1 1 calc R U . . .
C10 C 0.7501(6) 0.9102(4) 0.3222(2) 0.0678(9) Uani 1 1 d . . . . .
H10 H 0.842234 0.978339 0.341685 0.081 Uiso 1 1 calc R U . . .
C3 C 0.0423(6) 0.5403(4) 0.15550(19) 0.0622(8) Uani 1 1 d . . . . .
C6 C 0.1705(6) 0.6494(4) 0.1919(2) 0.0659(9) Uani 1 1 d . . . . .
H6 H 0.116863 0.767162 0.180783 0.079 Uiso 1 1 calc R U . . .
C9 C 0.5956(7) 0.9817(4) 0.2626(3) 0.0886(12) Uani 1 1 d . . . . .
H9 H 0.581988 1.098861 0.240770 0.106 Uiso 1 1 calc R U . . .
C8 C 0.4573(8) 0.8806(5) 0.2341(3) 0.0971(13) Uani 1 1 d . . . . .
H8 H 0.350744 0.930865 0.192947 0.117 Uiso 1 1 calc R U . . .
C1 C -0.2664(7) 0.5067(5) 0.0733(2) 0.0832(11) Uani 1 1 d . . . . .
H1 H -0.399219 0.558536 0.041495 0.100 Uiso 1 1 calc R U . . .
C2 C -0.1488(7) 0.6117(5) 0.1064(2) 0.0746(10) Uani 1 1 d . . . . .
H2 H -0.198929 0.729926 0.095426 0.090 Uiso 1 1 calc R U . . .
C4 C 0.1056(8) 0.3655(5) 0.1682(3) 0.0972(14) Uani 1 1 d . . . . .
H4 H 0.231502 0.309451 0.202060 0.117 Uiso 1 1 calc R U . . .
C5 C -0.0192(10) 0.2752(5) 0.1302(3) 0.1125(16) Uani 1 1 d . . . . .
H5 H 0.031699 0.157264 0.138251 0.135 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 1.764(3) . ?
S1 C13 1.812(3) . ?
N2 C6 1.246(4) . ?
N2 C7 1.422(4) . ?
C16 C14 1.373(4) . ?
C16 C15 1.386(4) 2_756 ?
C16 C13 1.506(4) . ?
C15 C14 1.381(4) . ?
C15 H15 0.9300 . ?
N1 C1 1.303(5) . ?
N1 C5 1.328(5) . ?
C12 C7 1.391(4) . ?
C12 C11 1.394(4) . ?
O1 H1A 0.85(2) . ?
O1 H1B 0.86(2) . ?
C11 C10 1.369(4) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C7 C8 1.382(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C10 C9 1.346(5) . ?
C10 H10 0.9300 . ?
C3 C2 1.367(4) . ?
C3 C4 1.369(5) . ?
C3 C6 1.472(4) . ?
C6 H6 0.9300 . ?
C9 C8 1.383(5) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C1 C2 1.378(5) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C4 C5 1.363(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?

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 S1 C13 102.32(14) . . ?
C6 N2 C7 120.9(3) . . ?
C14 C16 C15 118.2(3) . 2_756 ?
C14 C16 C13 121.1(3) . . ?
C15 C16 C13 120.7(3) 2_756 . ?
C14 C15 C16 120.8(3) . 2_756 ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 2_756 . ?
C1 N1 C5 114.0(3) . . ?
C7 C12 C11 118.7(3) . . ?
C7 C12 S1 116.9(2) . . ?
C11 C12 S1 124.5(2) . . ?
H1A O1 H1B 103(5) . . ?
C10 C11 C12 121.1(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C16 C14 C15 121.1(3) . . ?
C16 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C8 C7 C12 118.8(3) . . ?
C8 C7 N2 124.5(3) . . ?
C12 C7 N2 116.6(3) . . ?
C16 C13 S1 109.49(19) . . ?
C16 C13 H13A 109.8 . . ?
S1 C13 H13A 109.8 . . ?
C16 C13 H13B 109.8 . . ?
S1 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C2 C3 C4 116.7(3) . . ?
C2 C3 C6 120.4(3) . . ?
C4 C3 C6 122.9(3) . . ?
N2 C6 C3 123.7(3) . . ?
N2 C6 H6 118.2 . . ?
C3 C6 H6 118.2 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C7 C8 C9 121.3(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
N1 C1 C2 125.4(4) . . ?
N1 C1 H1 117.3 . . ?
C2 C1 H1 117.3 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C5 C4 C3 118.8(4) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 125.8(4) . . ?
N1 C5 H5 117.1 . . ?
C4 C5 H5 117.1 . . ?

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.049

