# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 2069238'
loop_
_audit_author_name
_audit_author_address
Ning
;Ningbo university
China
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        4-4
_chemical_formula_moiety         'C17 H8 O4 S2, C16 H12 N2 S4'
_chemical_formula_sum            'C33 H20 N2 O4 S6'
_chemical_formula_weight         700.87
_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'
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'
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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.9649(4)
_cell_length_b                   13.9228(9)
_cell_length_c                   21.5360(14)
_cell_angle_alpha                106.716(2)
_cell_angle_beta                 91.562(2)
_cell_angle_gamma                103.885(2)
_cell_volume                     1931.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.92
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_T_max  0.9622
_exptl_absorpt_correction_T_min  0.8294
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            48135
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         2.11
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                6125
_reflns_number_total             8864
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.011
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.154
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         8864
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0777
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1525P)²+2.8269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2687
_refine_ls_wR_factor_ref         0.2920
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C17(H17), C6(H6), C12(H12), C16(H16), C13(H13), C9(H9), C10(H10),
 N2(H2), N1(H1), C27(H27), C33(H33), C30(H30), C24(H24), C19(H19), C31(H31),
 C21(H21), C18(H18), C22(H22), C32(H32)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S2 S -0.80475(16) 0.39745(8) -0.00340(5) 0.0438(3) Uani 1 d . . .
S1 S -0.86256(16) 0.57484(9) 0.10043(5) 0.0453(3) Uani 1 d . . .
O2 O 0.0085(6) 0.7383(4) 0.3553(2) 0.0884(15) Uani 1 d . . .
O1 O -0.2440(7) 0.7703(6) 0.4067(2) 0.132(3) Uani 1 d . . .
O4 O -0.0198(7) 0.1519(3) 0.0266(2) 0.0815(13) Uani 1 d . . .
O3 O 0.0014(6) 0.2119(3) 0.1335(2) 0.0734(11) Uani 1 d . . .
C2 C -0.6712(6) 0.5198(3) 0.1163(2) 0.0356(9) Uani 1 d . . .
C3 C -0.6460(5) 0.4376(3) 0.06930(19) 0.0347(8) Uani 1 d . . .
C4 C -0.5044(6) 0.3749(3) 0.0714(2) 0.0363(9) Uani 1 d . . .
C5 C -0.4319(6) 0.3257(3) 0.0142(2) 0.0432(10) Uani 1 d . . .
H5 H -0.4769 0.3310 -0.0254 0.052 Uiso 1 calc . . R
C17 C -0.6290(7) 0.5940(4) 0.2375(2) 0.0522(12) Uani 1 d . . .
H17 H -0.7657 0.5721 0.2383 0.063 Uiso 1 calc . . R
C6 C -0.2937(7) 0.2693(3) 0.0160(2) 0.0456(10) Uani 1 d . . .
H6 H -0.2474 0.2367 -0.0225 0.055 Uiso 1 calc . . R
C12 C -0.3441(7) 0.6101(4) 0.1790(2) 0.0554(12) Uani 1 d . . .
H12 H -0.2874 0.6000 0.1398 0.066 Uiso 1 calc . . R
C8 C -0.0717(7) 0.2019(4) 0.0750(3) 0.0519(12) Uani 1 d . . .
C14 C -0.3052(7) 0.6779(4) 0.2955(2) 0.0490(11) Uani 1 d . . .
C1 C -0.9315(6) 0.4941(3) 0.01990(19) 0.0371(9) Uani 1 d . . .
C16 C -0.5077(8) 0.6454(5) 0.2949(2) 0.0621(14) Uani 1 d . . .
H16 H -0.5643 0.6584 0.3341 0.074 Uiso 1 calc . . R
C13 C -0.2234(7) 0.6605(4) 0.2377(2) 0.0578(13) Uani 1 d . . .
H13 H -0.0864 0.6824 0.2375 0.069 Uiso 1 calc . . R
C7 C -0.2244(6) 0.2611(3) 0.0742(2) 0.0442(10) Uani 1 d . . .
C11 C -0.5474(6) 0.5751(3) 0.17879(19) 0.0372(9) Uani 1 d . . .
C9 C -0.2993(7) 0.3070(4) 0.1305(2) 0.0522(12) Uani 1 d . . .
H9 H -0.2548 0.3010 0.1700 0.063 Uiso 1 calc . . R
C10 C -0.4395(7) 0.3619(4) 0.1290(2) 0.0503(11) Uani 1 d . . .
H10 H -0.4911 0.3905 0.1674 0.060 Uiso 1 calc . . R
C15 C -0.1777(8) 0.7338(5) 0.3585(3) 0.0665(15) Uani 1 d . . .
S3 S 0.67492(19) 1.15871(10) 0.76396(6) 0.0545(4) Uani 1 d . . .
S5 S 1.01847(18) 1.15323(9) 0.86891(6) 0.0511(3) Uani 1 d . . .
S6 S 1.12224(19) 0.98718(11) 0.76716(6) 0.0575(4) Uani 1 d . . .
S4 S 0.7793(2) 0.98741(13) 0.66639(6) 0.0663(4) Uani 1 d . . .
N2 N 1.7213(6) 0.8852(4) 0.8638(3) 0.0632(12) Uani 1 d . . .
H2 H 1.8178 0.8579 0.8676 0.076 Uiso 1 calc . . R
N1 N 0.2161(7) 0.8414(5) 0.4682(2) 0.0794(16) Uani 1 d . . .
H1 H 0.1458 0.8044 0.4320 0.095 Uiso 1 calc . . R
C23 C 0.5603(7) 1.0193(4) 0.6476(2) 0.0494(11) Uani 1 d . . .
C20 C 0.4410(7) 0.9577(4) 0.5855(2) 0.0542(12) Uani 1 d . . .
C28 C 1.2530(6) 1.0255(3) 0.8448(2) 0.0435(10) Uani 1 d . . .
C27 C 1.2001(7) 1.0990(4) 0.8896(2) 0.0505(11) Uani 1 d . . .
H27 H 1.2604 1.1215 0.9322 0.061 Uiso 1 calc . . R
C29 C 1.4113(6) 0.9754(4) 0.8524(2) 0.0466(10) Uani 1 d . . .
C33 C 1.6734(8) 0.9490(4) 0.9141(3) 0.0622(14) Uani 1 d . . .
H33 H 1.7451 0.9637 0.9542 0.075 Uiso 1 calc . . R
C25 C 0.8295(6) 1.0741(4) 0.7455(2) 0.0455(10) Uani 1 d . . .
C26 C 0.9719(6) 1.0729(3) 0.7881(2) 0.0430(10) Uani 1 d . . .
C30 C 1.5214(8) 0.9965(4) 0.9112(3) 0.0591(13) Uani 1 d . . .
H30 H 1.4938 1.0423 0.9487 0.071 Uiso 1 calc . . R
C24 C 0.5186(7) 1.0980(4) 0.6922(3) 0.0549(12) Uani 1 d . . .
H24 H 0.4067 1.1202 0.6849 0.066 Uiso 1 calc . . R
C19 C 0.5107(8) 0.8902(5) 0.5380(3) 0.0753(18) Uani 1 d . . .
H19 H 0.6369 0.8814 0.5449 0.090 Uiso 1 calc . . R
C31 C 1.4629(8) 0.9062(4) 0.7986(3) 0.0594(13) Uani 1 d . . .
H31 H 1.3933 0.8893 0.7578 0.071 Uiso 1 calc . . R
C21 C 0.2498(8) 0.9654(5) 0.5722(3) 0.0761(18) Uani 1 d . . .
H21 H 0.1930 1.0098 0.6025 0.091 Uiso 1 calc . . R
C18 C 0.3968(9) 0.8355(6) 0.4804(3) 0.088(2) Uani 1 d . . .
H18 H 0.4504 0.7919 0.4484 0.105 Uiso 1 calc . . R
C22 C 0.1468(9) 0.9051(6) 0.5126(3) 0.083(2) Uani 1 d . . .
H22 H 0.0191 0.9105 0.5038 0.100 Uiso 1 calc . . R
C32 C 1.6174(8) 0.8628(5) 0.8060(3) 0.0686(15) Uani 1 d . . .
H32 H 1.6501 0.8166 0.7698 0.082 Uiso 1 calc . . R


_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
S2 C3 1.759(4) . ?
S2 C1 1.746(4) . ?
S1 C2 1.760(4) . ?
S1 C1 1.754(4) . ?
O2 C15 1.288(7) . ?
O1 C15 1.177(7) . ?
O4 C8 1.193(6) . ?
O3 C8 1.301(6) . ?
C2 C3 1.343(6) . ?
C2 C11 1.473(5) . ?
C3 C4 1.473(5) . ?
C4 C5 1.398(6) . ?
C4 C10 1.383(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(6) . ?
C17 H17 0.9300 . ?
C17 C16 1.378(6) . ?
C17 C11 1.382(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.395(6) . ?
C12 C11 1.383(6) . ?
C8 C7 1.497(6) . ?
C14 C16 1.373(7) . ?
C14 C13 1.365(7) . ?
C14 C15 1.493(6) . ?
C1 C1 1.336(7) 2_365 ?
C16 H16 0.9300 . ?
C13 H13 0.9300 . ?
C7 C9 1.378(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(6) . ?
C10 H10 0.9300 . ?
S3 C25 1.752(4) . ?
S3 C24 1.734(5) . ?
S5 C27 1.730(5) . ?
S5 C26 1.750(4) . ?
S6 C28 1.754(4) . ?
S6 C26 1.743(4) . ?
S4 C23 1.755(5) . ?
S4 C25 1.751(5) . ?
N2 H2 0.8600 . ?
N2 C33 1.296(7) . ?
N2 C32 1.337(7) . ?
N1 H1 0.8600 . ?
N1 C18 1.305(7) . ?
N1 C22 1.295(8) . ?
C23 C20 1.467(6) . ?
C23 C24 1.330(7) . ?
C20 C19 1.363(7) . ?
C20 C21 1.390(7) . ?
C28 C27 1.323(6) . ?
C28 C29 1.467(6) . ?
C27 H27 0.9300 . ?
C29 C30 1.379(7) . ?
C29 C31 1.395(7) . ?
C33 H33 0.9300 . ?
C33 C30 1.385(7) . ?
C25 C26 1.339(6) . ?
C30 H30 0.9300 . ?
C24 H24 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.364(7) . ?
C31 H31 0.9300 . ?
C31 C32 1.381(7) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(8) . ?
C18 H18 0.9300 . ?
C22 H22 0.9300 . ?
C32 H32 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
C1 S2 C3 96.37(18) . . ?
C1 S1 C2 95.65(18) . . ?
C3 C2 S1 117.4(3) . . ?
C3 C2 C11 127.5(3) . . ?
C11 C2 S1 115.0(3) . . ?
C2 C3 S2 116.4(3) . . ?
C2 C3 C4 128.1(3) . . ?
C4 C3 S2 115.5(3) . . ?
C5 C4 C3 120.3(4) . . ?
C10 C4 C3 121.9(4) . . ?
C10 C4 C5 117.8(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.6 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C11 120.0(4) . . ?
C11 C17 H17 120.0 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H6 119.7 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.3(5) . . ?
O4 C8 O3 123.5(4) . . ?
O4 C8 C7 123.1(5) . . ?
O3 C8 C7 113.4(5) . . ?
C16 C14 C15 120.1(5) . . ?
C13 C14 C16 119.0(4) . . ?
C13 C14 C15 120.8(5) . . ?
S2 C1 S1 114.0(2) . . ?
C1 C1 S2 123.2(4) 2_365 . ?
C1 C1 S1 122.9(4) 2_365 . ?
C17 C16 H16 119.3 . . ?
C14 C16 C17 121.4(5) . . ?
C14 C16 H16 119.3 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C6 C7 C8 119.5(4) . . ?
C6 C7 C9 119.0(4) . . ?
C9 C7 C8 121.5(4) . . ?
C17 C11 C2 121.9(4) . . ?
C17 C11 C12 118.8(4) . . ?
C12 C11 C2 119.3(4) . . ?
C7 C9 H9 119.6 . . ?
C7 C9 C10 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
C4 C10 H10 119.5 . . ?
C9 C10 C4 121.0(4) . . ?
C9 C10 H10 119.5 . . ?
O2 C15 C14 114.5(5) . . ?
O1 C15 O2 123.5(5) . . ?
O1 C15 C14 122.1(5) . . ?
C24 S3 C25 94.5(2) . . ?
C27 S5 C26 94.4(2) . . ?
C26 S6 C28 95.6(2) . . ?
C25 S4 C23 95.3(2) . . ?
C33 N2 H2 120.7 . . ?
C33 N2 C32 118.5(4) . . ?
C32 N2 H2 120.7 . . ?
C18 N1 H1 121.3 . . ?
C22 N1 H1 121.3 . . ?
C22 N1 C18 117.4(5) . . ?
C20 C23 S4 118.0(4) . . ?
C24 C23 S4 115.7(3) . . ?
C24 C23 C20 126.2(4) . . ?
C19 C20 C23 122.1(4) . . ?
C19 C20 C21 116.6(5) . . ?
C21 C20 C23 121.3(5) . . ?
C27 C28 S6 115.5(3) . . ?
C27 C28 C29 127.3(4) . . ?
C29 C28 S6 117.2(3) . . ?
S5 C27 H27 120.1 . . ?
C28 C27 S5 119.8(3) . . ?
C28 C27 H27 120.1 . . ?
C30 C29 C28 122.9(5) . . ?
C30 C29 C31 116.6(4) . . ?
C31 C29 C28 120.5(4) . . ?
N2 C33 H33 118.2 . . ?
N2 C33 C30 123.6(5) . . ?
C30 C33 H33 118.2 . . ?
S4 C25 S3 114.4(2) . . ?
C26 C25 S3 123.7(4) . . ?
C26 C25 S4 121.9(4) . . ?
S6 C26 S5 114.6(2) . . ?
C25 C26 S5 123.5(4) . . ?
C25 C26 S6 121.9(4) . . ?
C29 C30 C33 119.4(5) . . ?
C29 C30 H30 120.3 . . ?
C33 C30 H30 120.3 . . ?
S3 C24 H24 120.3 . . ?
C23 C24 S3 119.4(3) . . ?
C23 C24 H24 120.3 . . ?
C20 C19 H19 119.8 . . ?
C20 C19 C18 120.5(5) . . ?
C18 C19 H19 119.8 . . ?
C29 C31 H31 120.1 . . ?
C32 C31 C29 119.9(5) . . ?
C32 C31 H31 120.1 . . ?
C20 C21 H21 121.0 . . ?
C22 C21 C20 118.0(6) . . ?
C22 C21 H21 121.0 . . ?
N1 C18 C19 123.1(6) . . ?
N1 C18 H18 118.4 . . ?
C19 C18 H18 118.4 . . ?
N1 C22 C21 124.4(5) . . ?
N1 C22 H22 117.8 . . ?
C21 C22 H22 117.8 . . ?
N2 C32 C31 121.9(6) . . ?
N2 C32 H32 119.1 . . ?
C31 C32 H32 119.1 . . ?

_olex2_submission_original_sample_id 4-4
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2069241'
loop_
_audit_author_name
_audit_author_address
Ning
;Ningbo university
China
;
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_audit_creation_date             2021-02-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        3
_chemical_formula_moiety         'C16 H10 N2 S4, C17 H10 O4 S2'
_chemical_formula_sum            'C33 H20 N2 O4 S6'
_chemical_formula_weight         700.87
_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'
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'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   6.2610(3)
_cell_length_b                   19.6413(9)
_cell_length_c                   32.8415(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.9380(10)
_cell_angle_gamma                90.00
_cell_volume                     4023.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9151
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.42
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_correction_T_min  0.9291
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'dull dark red'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            79963
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.14
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                6251
_reflns_number_total             9236
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.352
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.193
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.650
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         9236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1548
_refine_ls_R_factor_gt           0.1219
_refine_ls_restrained_S_all      1.650
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3874
_refine_ls_wR_factor_ref         0.4128
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3A), C4(H4), C7(H7), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C20(H20), C21(H21), C22(H22), C28(H28), C29(H29),
  C30(H30), C31(H31)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.9561(3) 0.48338(9) 0.28539(5) 0.0798(5) Uani 1 d . . .
S2 S 0.9818(3) 0.34666(11) 0.24926(6) 0.0939(6) Uani 1 d . . .
S3 S 0.5524(2) 0.43427(7) 0.33364(4) 0.0652(4) Uani 1 d . . .
S4 S 0.5780(3) 0.29886(8) 0.29628(5) 0.0848(5) Uani 1 d . . .
N1 N 0.1397(7) 0.4655(2) 0.43315(14) 0.0696(12) Uani 1 d . . .
N2 N 1.5723(9) 0.5760(3) 0.20832(18) 0.0894(16) Uani 1 d . . .
C1 C 1.5542(14) 0.6348(4) 0.2280(3) 0.106(2) Uani 1 d . . .
H1 H 1.6468 0.6703 0.2231 0.127 Uiso 1 calc . . R
C2 C 1.404(2) 0.6441(4) 0.2549(3) 0.157(5) Uani 1 d . . .
H2A H 1.3890 0.6860 0.2675 0.188 Uiso 1 calc . . R
C3 C 1.4437(10) 0.5244(4) 0.21635(19) 0.0850(18) Uani 1 d . . .
H3A H 1.4603 0.4831 0.2031 0.102 Uiso 1 calc . . R
C4 C 1.2731(16) 0.5896(5) 0.2630(3) 0.125(3) Uani 1 d . . .
H4 H 1.1739 0.5946 0.2823 0.150 Uiso 1 calc . . R
C5 C 1.2869(9) 0.5296(3) 0.24341(16) 0.0726(15) Uani 1 d . . .
C6 C 1.1521(9) 0.4703(4) 0.25045(16) 0.0743(16) Uani 1 d . . .
C7 C 1.1567(12) 0.4082(4) 0.2348(2) 0.096(2) Uani 1 d . . .
H7 H 1.2546 0.3978 0.2160 0.115 Uiso 1 calc . . R
C8 C 0.8493(8) 0.4020(3) 0.28112(16) 0.0676(14) Uani 1 d . . .
C9 C 0.6841(9) 0.3822(3) 0.30133(17) 0.0657(13) Uani 1 d . . .
C10 C 0.3971(10) 0.3107(3) 0.33219(18) 0.0722(15) Uani 1 d . . .
H10 H 0.3097 0.2749 0.3391 0.087 Uiso 1 calc . . R
C11 C 0.3826(8) 0.3707(2) 0.34986(15) 0.0552(11) Uani 1 d . . .
C12 C 0.2333(7) 0.3888(2) 0.38019(14) 0.0520(11) Uani 1 d . . .
C13 C 0.2727(9) 0.4459(3) 0.40526(17) 0.0656(13) Uani 1 d . . .
H13 H 0.3961 0.4713 0.4025 0.079 Uiso 1 calc . . R
C14 C 0.0517(9) 0.3514(3) 0.38536(16) 0.0657(13) Uani 1 d . . .
H14 H 0.0205 0.3125 0.3698 0.079 Uiso 1 calc . . R
C15 C -0.0846(9) 0.3728(3) 0.41423(17) 0.0704(14) Uani 1 d . . .
H15 H -0.2078 0.3480 0.4182 0.084 Uiso 1 calc . . R
C16 C -0.0363(9) 0.4302(3) 0.43668(17) 0.0700(14) Uani 1 d . . .
H16 H -0.1313 0.4449 0.4551 0.084 Uiso 1 calc . . R
S5 S 0.92177(19) 0.89332(6) 0.48717(4) 0.0607(4) Uani 1 d . . .
S6 S 0.74315(19) 0.99411(6) 0.54093(4) 0.0605(4) Uani 1 d . . .
O1 O -0.0771(7) 0.8224(2) 0.66348(14) 0.0886(13) Uani 1 d . . .
O2 O -0.1169(8) 0.9337(2) 0.65994(15) 0.0933(14) Uani 1 d . . .
H2 H -0.2120 0.9263 0.6750 0.140 Uiso 1 calc . . GR
O3 O 0.2555(6) 0.58127(18) 0.47044(13) 0.0725(10) Uani 1 d . . .
H3 H 0.2268 0.5429 0.4618 0.109 Uiso 1 calc . . GR
O4 O 0.5888(6) 0.5511(2) 0.46126(15) 0.0859(13) Uani 1 d . . .
C17 C 0.4636(8) 0.5912(2) 0.47153(15) 0.0574(12) Uani 1 d . . .
C18 C 0.5262(7) 0.6625(2) 0.48527(14) 0.0506(10) Uani 1 d . . .
C19 C 0.3754(8) 0.7134(3) 0.48783(18) 0.0662(14) Uani 1 d . . .
H19 H 0.2306 0.7033 0.4825 0.079 Uiso 1 calc . . R
C20 C 0.7375(8) 0.6774(2) 0.49470(18) 0.0634(13) Uani 1 d . . .
H20 H 0.8403 0.6435 0.4933 0.076 Uiso 1 calc . . R
C21 C 0.8010(7) 0.7435(2) 0.50653(18) 0.0617(13) Uani 1 d . . .
H21 H 0.9449 0.7530 0.5136 0.074 Uiso 1 calc . . R
C22 C 0.4365(7) 0.7780(2) 0.49802(17) 0.0602(13) Uani 1 d . . .
H22 H 0.3333 0.8120 0.4985 0.072 Uiso 1 calc . . R
C23 C 0.6501(7) 0.7939(2) 0.50764(14) 0.0464(10) Uani 1 d . . .
C24 C 0.7201(7) 0.8655(2) 0.51648(14) 0.0504(10) Uani 1 d . . .
C25 C 0.9312(7) 0.9760(2) 0.50585(15) 0.0538(11) Uani 1 d . . .
C26 C 0.6379(6) 0.9110(2) 0.54148(14) 0.0478(10) Uani 1 d . . .
C27 C 0.4736(6) 0.9010(2) 0.57065(14) 0.0482(10) Uani 1 d . . .
C28 C 0.4383(8) 0.8389(2) 0.58908(17) 0.0594(12) Uani 1 d . . .
H28 H 0.5233 0.8017 0.5836 0.071 Uiso 1 calc . . R
C29 C 0.3463(8) 0.9559(3) 0.58081(17) 0.0620(12) Uani 1 d . . .
H29 H 0.3691 0.9984 0.5696 0.074 Uiso 1 calc . . R
C30 C 0.1886(7) 0.9484(3) 0.60695(16) 0.0618(12) Uani 1 d . . .
H30 H 0.1087 0.9859 0.6139 0.074 Uiso 1 calc . . R
C31 C 0.2776(8) 0.8313(3) 0.61563(16) 0.0629(13) Uani 1 d . . .
H31 H 0.2580 0.7897 0.6283 0.075 Uiso 1 calc . . R
C32 C 0.1487(7) 0.8856(2) 0.62290(14) 0.0524(11) Uani 1 d . . .
C33 C -0.0257(8) 0.8764(3) 0.65122(16) 0.0619(13) Uani 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 C6 1.770(5) . ?
S1 C8 1.733(6) . ?
S2 C7 1.725(8) . ?
S2 C8 1.765(6) . ?
S3 C9 1.733(6) . ?
S3 C11 1.753(5) . ?
S4 C9 1.769(6) . ?
S4 C10 1.720(6) . ?
N1 C13 1.346(7) . ?
N1 C16 1.316(7) . ?
N2 C1 1.332(10) . ?
N2 C3 1.335(9) . ?
C1 H1 0.9300 . ?
C1 C2 1.357(11) . ?
C2 H2A 0.9300 . ?
C2 C4 1.388(12) . ?
C3 H3A 0.9300 . ?
C3 C5 1.384(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.350(10) . ?
C5 C6 1.467(9) . ?
C6 C7 1.325(10) . ?
C7 H7 0.9300 . ?
C8 C9 1.334(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.320(7) . ?
C11 C12 1.468(7) . ?
C12 C13 1.400(7) . ?
C12 C14 1.376(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.394(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.368(8) . ?
C16 H16 0.9300 . ?
S5 C24 1.740(4) . ?
S5 C25 1.735(5) . ?
S6 C25 1.753(5) . ?
S6 C26 1.760(4) . ?
O1 C33 1.188(7) . ?
O2 H2 0.8200 . ?
O2 C33 1.306(7) . ?
O3 H3 0.8200 . ?
O3 C17 1.315(6) . ?
O4 C17 1.181(6) . ?
C17 C18 1.512(6) . ?
C18 C19 1.382(6) . ?
C18 C20 1.365(7) . ?
C19 H19 0.9300 . ?
C19 C22 1.359(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.402(7) . ?
C21 H21 0.9300 . ?
C21 C23 1.372(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(6) . ?
C23 C24 1.493(6) . ?
C24 C26 1.346(6) . ?
C25 C25 1.355(9) 3_776 ?
C26 C27 1.478(6) . ?
C27 C28 1.387(7) . ?
C27 C29 1.398(6) . ?
C28 H28 0.9300 . ?
C28 C31 1.395(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.371(7) . ?
C30 H30 0.9300 . ?
C30 C32 1.370(7) . ?
C31 H31 0.9300 . ?
C31 C32 1.372(7) . ?
C32 C33 1.505(6) . ?

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
C8 S1 C6 95.7(3) . . ?
C7 S2 C8 94.2(3) . . ?
C9 S3 C11 95.7(3) . . ?
C10 S4 C9 94.3(3) . . ?
C16 N1 C13 118.7(5) . . ?
C1 N2 C3 119.0(6) . . ?
N2 C1 H1 119.2 . . ?
N2 C1 C2 121.7(7) . . ?
C2 C1 H1 119.2 . . ?
C1 C2 H2A 120.8 . . ?
C1 C2 C4 118.4(8) . . ?
C4 C2 H2A 120.8 . . ?
N2 C3 H3A 118.5 . . ?
N2 C3 C5 123.0(7) . . ?
C5 C3 H3A 118.5 . . ?
C2 C4 H4 119.4 . . ?
C5 C4 C2 121.3(7) . . ?
C5 C4 H4 119.4 . . ?
C3 C5 C6 119.5(6) . . ?
C4 C5 C3 116.6(6) . . ?
C4 C5 C6 123.8(5) . . ?
C5 C6 S1 115.3(5) . . ?
C7 C6 S1 115.1(5) . . ?
C7 C6 C5 129.6(5) . . ?
S2 C7 H7 119.9 . . ?
C6 C7 S2 120.2(4) . . ?
C6 C7 H7 119.9 . . ?
S1 C8 S2 114.7(3) . . ?
C9 C8 S1 122.6(5) . . ?
C9 C8 S2 122.6(5) . . ?
S3 C9 S4 114.2(3) . . ?
C8 C9 S3 124.2(5) . . ?
C8 C9 S4 121.6(5) . . ?
S4 C10 H10 120.1 . . ?
C11 C10 S4 119.7(4) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 S3 115.9(4) . . ?
C10 C11 C12 126.0(5) . . ?
C12 C11 S3 118.1(4) . . ?
C13 C12 C11 120.2(4) . . ?
C14 C12 C11 122.3(4) . . ?
C14 C12 C13 117.4(5) . . ?
N1 C13 C12 122.8(5) . . ?
N1 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
C12 C14 H14 120.5 . . ?
C12 C14 C15 119.0(5) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
N1 C16 C15 122.4(5) . . ?
N1 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C25 S5 C24 95.9(2) . . ?
C25 S6 C26 95.3(2) . . ?
C33 O2 H2 109.5 . . ?
C17 O3 H3 109.5 . . ?
O3 C17 C18 112.1(4) . . ?
O4 C17 O3 125.0(5) . . ?
O4 C17 C18 122.8(5) . . ?
C19 C18 C17 121.8(4) . . ?
C20 C18 C17 119.2(4) . . ?
C20 C18 C19 119.0(4) . . ?
C18 C19 H19 119.6 . . ?
C22 C19 C18 120.8(4) . . ?
C22 C19 H19 119.6 . . ?
C18 C20 H20 119.7 . . ?
C18 C20 C21 120.5(4) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.1 . . ?
C23 C21 C20 119.8(4) . . ?
C23 C21 H21 120.1 . . ?
C19 C22 H22 119.5 . . ?
C19 C22 C23 120.9(4) . . ?
C23 C22 H22 119.5 . . ?
C21 C23 C22 119.0(4) . . ?
C21 C23 C24 119.6(4) . . ?
C22 C23 C24 121.3(4) . . ?
C23 C24 S5 113.7(3) . . ?
C26 C24 S5 117.6(3) . . ?
C26 C24 C23 128.5(4) . . ?
S5 C25 S6 114.7(2) . . ?
C25 C25 S5 123.6(5) 3_776 . ?
C25 C25 S6 121.7(5) 3_776 . ?
C24 C26 S6 116.5(3) . . ?
C24 C26 C27 129.1(4) . . ?
C27 C26 S6 114.4(3) . . ?
C28 C27 C26 123.1(4) . . ?
C28 C27 C29 117.2(4) . . ?
C29 C27 C26 119.6(4) . . ?
C27 C28 H28 119.4 . . ?
C27 C28 C31 121.2(4) . . ?
C31 C28 H28 119.4 . . ?
C27 C29 H29 119.2 . . ?
C30 C29 C27 121.5(5) . . ?
C30 C29 H29 119.2 . . ?
C29 C30 H30 120.0 . . ?
C32 C30 C29 120.1(5) . . ?
C32 C30 H30 120.0 . . ?
C28 C31 H31 120.3 . . ?
C32 C31 C28 119.5(5) . . ?
C32 C31 H31 120.3 . . ?
C30 C32 C31 120.2(4) . . ?
C30 C32 C33 120.7(4) . . ?
C31 C32 C33 118.9(5) . . ?
O1 C33 O2 124.0(5) . . ?
O1 C33 C32 123.3(5) . . ?
O2 C33 C32 112.7(5) . . ?

_olex2_submission_original_sample_id 3
_olex2_submission_special_instructions 'No special instructions were received'
