# Electronic Supplementary Material (ESI) for Nanoscale.
# This journal is © The Royal Society of Chemistry 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_ml-285
_database_code_depnum_ccdc_archive 'CCDC 1896561'
loop_
_audit_author_name
_audit_author_address
'Olaf Fuhr'
;Karlsruher Institut fuer Technologie
Germany
;
_audit_update_record             
;
2019-02-11 deposited with the CCDC.	2019-06-14 downloaded from the CCDC.
;
_audit_creation_date             2016-05-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C33 H28 O4 S4'
_chemical_formula_sum            'C33 H28 O4 S4'
_chemical_formula_weight         616.79
_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'
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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   20.2681(16)
_cell_length_b                   20.2681(16)
_cell_length_c                   7.1102(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2920.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13424
_cell_measurement_temperature    180.15
_cell_measurement_theta_max      26.11
_cell_measurement_theta_min      1.42
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_correction_T_min  0.9100
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1288
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0770
0 -1 0 0.0120
1 0 0 0.0590
-1 0 0 0.0220
1 0 1 0.1600
-1 0 -1 0.2150

_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1318
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13369
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.662
_diffrn_reflns_theta_min         2.010
_diffrn_ambient_temperature      180.15
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube, 12 x 0.4 mm fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_target            Mo
_diffrn_source_type              'sealed X-ray tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1154
_reflns_number_total             1375
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+1.1484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0796
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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 0.82473(2) 0.40405(2) 0.07864(7) 0.03512(16) Uani 1 1 d . . . . .
O1 O 0.77011(6) 0.28817(6) 0.0116(2) 0.0509(4) Uani 1 1 d . . . . .
C1 C 1.0000 0.2500 0.6250 0.0248(6) Uani 1 4 d S T P . .
C2 C 0.95200(7) 0.28760(7) 0.4934(2) 0.0238(3) Uani 1 1 d . . . . .
C3 C 0.97919(8) 0.32706(7) 0.3519(2) 0.0266(3) Uani 1 1 d . . . . .
H3 H 1.0253(9) 0.3308(8) 0.343(3) 0.033(4) Uiso 1 1 d . . . . .
C4 C 0.94012(8) 0.36079(7) 0.2255(2) 0.0270(3) Uani 1 1 d . . . . .
H4 H 0.9590(8) 0.3865(8) 0.130(3) 0.032(5) Uiso 1 1 d . . . . .
C5 C 0.87181(7) 0.35604(7) 0.2374(2) 0.0268(3) Uani 1 1 d . . . . .
C6 C 0.84359(7) 0.31722(7) 0.3764(2) 0.0277(3) Uani 1 1 d . . . . .
H6 H 0.7961(9) 0.3140(8) 0.389(3) 0.030(4) Uiso 1 1 d . . . . .
C7 C 0.88366(7) 0.28307(7) 0.5021(2) 0.0262(3) Uani 1 1 d . . . . .
H7 H 0.8644(8) 0.2570(8) 0.592(3) 0.027(4) Uiso 1 1 d . . . . .
C8 C 0.77127(8) 0.34528(9) -0.0294(3) 0.0367(4) Uani 1 1 d . . . . .
C9 C 0.72807(11) 0.37579(13) -0.1763(3) 0.0527(5) Uani 1 1 d . . . . .
H9A H 0.7372(13) 0.4234(14) -0.192(4) 0.086(9) Uiso 1 1 d . . . . .
H9B H 0.6832(14) 0.3722(12) -0.142(4) 0.078(8) Uiso 1 1 d . . . . .
H9C H 0.7371(15) 0.3530(16) -0.285(5) 0.105(11) Uiso 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
S1 C5 1.7698(16) . ?
S1 C8 1.7843(18) . ?
O1 C8 1.194(2) . ?
C1 C2 1.5501(14) 14_666 ?
C1 C2 1.5502(14) . ?
C1 C2 1.5501(14) 3_755 ?
C1 C2 1.5501(14) 16_646 ?
C2 C3 1.398(2) . ?
C2 C7 1.390(2) . ?
C3 H3 0.941(18) . ?
C3 C4 1.379(2) . ?
C4 H4 0.938(19) . ?
C4 C5 1.390(2) . ?
C5 C6 1.387(2) . ?
C6 H6 0.969(17) . ?
C6 C7 1.392(2) . ?
C7 H7 0.917(18) . ?
C8 C9 1.497(3) . ?
C9 H9A 0.99(3) . ?
C9 H9B 0.94(3) . ?
C9 H9C 0.92(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
C5 S1 C8 103.60(8) . . ?
C2 C1 C2 111.38(5) 14_666 3_755 ?
C2 C1 C2 105.72(10) 14_666 16_646 ?
C2 C1 C2 105.72(10) 3_755 . ?
C2 C1 C2 111.38(5) 14_666 . ?
C2 C1 C2 111.38(5) 16_646 3_755 ?
C2 C1 C2 111.38(5) 16_646 . ?
C3 C2 C1 117.91(11) . . ?
C7 C2 C1 124.48(12) . . ?
C7 C2 C3 117.57(14) . . ?
C2 C3 H3 119.2(12) . . ?
C4 C3 C2 121.74(14) . . ?
C4 C3 H3 119.0(12) . . ?
C3 C4 H4 120.9(10) . . ?
C3 C4 C5 119.83(15) . . ?
C5 C4 H4 119.2(10) . . ?
C4 C5 S1 117.38(12) . . ?
C6 C5 S1 122.97(11) . . ?
C6 C5 C4 119.58(14) . . ?
C5 C6 H6 121.0(11) . . ?
C5 C6 C7 119.94(14) . . ?
C7 C6 H6 119.1(11) . . ?
C2 C7 C6 121.33(14) . . ?
C2 C7 H7 119.6(10) . . ?
C6 C7 H7 119.0(10) . . ?
O1 C8 S1 123.65(14) . . ?
O1 C8 C9 124.02(18) . . ?
C9 C8 S1 112.33(15) . . ?
C8 C9 H9A 111.7(17) . . ?
C8 C9 H9B 110.6(18) . . ?
C8 C9 H9C 105(2) . . ?
H9A C9 H9B 107(2) . . ?
H9A C9 H9C 111(3) . . ?
H9B C9 H9C 112(3) . . ?

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
S1 C5 C6 C7 -177.03(12) . . . . ?
C1 C2 C3 C4 178.22(12) . . . . ?
C1 C2 C7 C6 -178.56(12) . . . . ?
C2 C1 C2 C3 -172.81(13) 16_646 . . . ?
C2 C1 C2 C3 69.43(8) 14_666 . . . ?
C2 C1 C2 C3 -51.69(10) 3_755 . . . ?
C2 C1 C2 C7 -112.85(17) 14_666 . . . ?
C2 C1 C2 C7 4.91(14) 16_646 . . . ?
C2 C1 C2 C7 126.03(15) 3_755 . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C2 C7 C6 -0.8(2) . . . . ?
C3 C4 C5 S1 176.73(12) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C7 -0.3(2) . . . . ?
C5 S1 C8 O1 2.28(19) . . . . ?
C5 S1 C8 C9 -177.94(15) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
C7 C2 C3 C4 0.3(2) . . . . ?
C8 S1 C5 C4 126.75(13) . . . . ?
C8 S1 C5 C6 -56.48(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
