# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_C4DBTA
_database_code_depnum_ccdc_archive 'CCDC 1956921'
loop_
_audit_author_name
_audit_author_address
'Naoki Aratani'
;Nara Institute of Science and Technology
Japan
;
_audit_update_record             
;
2019-10-01 deposited with the CCDC.	2020-01-13 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         'C38 H34 S4'
_chemical_formula_sum            'C38 H34 S4'
_chemical_formula_weight         618.89

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'
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                   41.708(10)
_cell_length_b                   5.7563(10)
_cell_length_c                   12.670(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.46(2)
_cell_angle_gamma                90
_cell_volume                     3008.7(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    192
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      22.52

_exptl_crystal_description       prism

_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.344
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.413
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            6462
_diffrn_reflns_av_unetI/netI     0.2017
_diffrn_reflns_av_R_equivalents  0.1835
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.975
_diffrn_reflns_theta_max         23.497
_diffrn_reflns_theta_full        23.497
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2237
_reflns_number_gt                1219
_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       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'

_diffrn_radiation_source         'fine-focus sealed tube'


_diffrn_radiation_monochromator  graphite

_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_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)+(0.0436P)²+7.9117P] 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         2237
_refine_ls_number_parameters     220
_refine_ls_number_restraints     168
_refine_ls_R_factor_all          0.1902
_refine_ls_R_factor_gt           0.1043
_refine_ls_wR_factor_ref         0.2208
_refine_ls_wR_factor_gt          0.1784
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.31109(19) 0.0220(13) 0.2202(6) 0.0152(18) Uani 1 1 d . U . . .
H1 H 0.3263 -0.0753 0.2587 0.018 Uiso 1 1 calc R U . . .
C2 C 0.29589(18) -0.0469(13) 0.1224(6) 0.0155(19) Uani 1 1 d . U . . .
H2 H 0.3010 -0.1910 0.0962 0.019 Uiso 1 1 calc R U . . .
C3 C 0.22760(19) 0.4059(13) -0.0590(6) 0.0157(19) Uani 1 1 d . U . . .
C4 C 0.24226(19) 0.4609(14) 0.0419(6) 0.0180(19) Uani 1 1 d . U . . .
H4 H 0.2369 0.6018 0.0707 0.022 Uiso 1 1 calc R U . . .
C5 C 0.26508(19) 0.3173(14) 0.1054(6) 0.0171(18) Uani 1 1 d . U . . .
C6 C 0.28069(18) 0.3827(14) 0.2068(6) 0.0175(18) Uani 1 1 d . U . . .
H6 H 0.2753 0.5233 0.2358 0.021 Uiso 1 1 calc R U . . .
C7 C 0.30395(19) 0.2424(14) 0.2646(6) 0.0171(18) Uani 1 1 d . U . . .
C8 C 0.32078(19) 0.3167(14) 0.3677(6) 0.0175(18) Uani 1 1 d . U . . .
C9 C 0.31804(19) 0.5157(14) 0.4223(6) 0.0204(19) Uani 1 1 d . U . . .
H9 H 0.3035 0.6325 0.3969 0.025 Uiso 1 1 calc R U . . .
C10 C 0.33913(18) 0.5340(14) 0.5222(6) 0.0181(19) Uani 1 1 d . U . . .
H10 H 0.3395 0.6602 0.5682 0.022 Uiso 1 1 calc R U . . .
C11 C 0.35891(19) 0.3388(14) 0.5416(6) 0.0183(18) Uani 1 1 d . U . . .
C12 C 0.38143(19) 0.2886(14) 0.6372(6) 0.0160(18) Uani 1 1 d . U . . .
C13 C 0.4009(2) 0.0992(14) 0.6605(6) 0.026(2) Uani 1 1 d . U . . .
H13 H 0.4022 -0.0221 0.6128 0.031 Uiso 1 1 calc R U . . .
C14 C 0.4192(2) 0.1054(16) 0.7657(6) 0.029(2) Uani 1 1 d . U . . .
H14 H 0.4336 -0.0107 0.7932 0.034 Uiso 1 1 calc R U . . .
C15 C 0.4133(2) 0.2977(16) 0.8199(7) 0.026(2) Uani 1 1 d . U . . .
C16 C 0.4257(2) 0.3618(18) 0.9336(7) 0.037(2) Uani 1 1 d . U . . .
H23 H 0.4276 0.5297 0.9372 0.044 Uiso 0.495(8) 1 calc R U P A 1
H24 H 0.4092 0.3178 0.9766 0.044 Uiso 0.495(8) 1 calc R U P A 1
H25 H 0.4068 0.3812 0.9692 0.044 Uiso 0.505(8) 1 calc R U P A 2
H26 H 0.4373 0.2274 0.9658 0.044 Uiso 0.505(8) 1 calc R U P A 2
C17 C 0.4556(4) 0.267(3) 0.9826(13) 0.029(3) Uani 0.495(8) 1 d . U P A 1
H17A H 0.4721 0.2993 0.9382 0.034 Uiso 0.495(8) 1 calc R U P A 1
H17B H 0.4535 0.0996 0.9873 0.034 Uiso 0.495(8) 1 calc R U P A 1
C18 C 0.4669(4) 0.368(3) 1.0987(14) 0.029(3) Uani 0.495(8) 1 d . U P A 1
H18A H 0.4722 0.5318 1.0935 0.035 Uiso 0.495(8) 1 calc R U P A 1
H18B H 0.4494 0.3553 1.1408 0.035 Uiso 0.495(8) 1 calc R U P A 1
C19 C 0.4971(5) 0.235(3) 1.1549(14) 0.042(5) Uani 0.495(8) 1 d . U P A 1
H19A H 0.4927 0.0711 1.1524 0.064 Uiso 0.495(8) 1 calc R U P A 1
H19B H 0.5018 0.2842 1.2280 0.064 Uiso 0.495(8) 1 calc R U P A 1
H19C H 0.5153 0.2669 1.1192 0.064 Uiso 0.495(8) 1 calc R U P A 1
C20 C 0.4447(4) 0.546(3) 0.9599(13) 0.029(3) Uani 0.505(8) 1 d . U P A 2
H20A H 0.4315 0.6850 0.9501 0.035 Uiso 0.505(8) 1 calc R U P A 2
H20B H 0.4605 0.5551 0.9107 0.035 Uiso 0.505(8) 1 calc R U P A 2
C21 C 0.4633(4) 0.546(3) 1.0751(14) 0.028(3) Uani 0.505(8) 1 d . U P A 2
H21A H 0.4478 0.5197 1.1240 0.034 Uiso 0.505(8) 1 calc R U P A 2
H21B H 0.4783 0.4171 1.0824 0.034 Uiso 0.505(8) 1 calc R U P A 2
C22 C 0.4819(4) 0.765(3) 1.1089(14) 0.031(5) Uani 0.505(8) 1 d . U P A 2
H22A H 0.4978 0.7920 1.0626 0.046 Uiso 0.505(8) 1 calc R U P A 2
H22B H 0.4925 0.7488 1.1810 0.046 Uiso 0.505(8) 1 calc R U P A 2
H22C H 0.4672 0.8946 1.1045 0.046 Uiso 0.505(8) 1 calc R U P A 2
S1 S 0.35144(5) 0.1405(4) 0.43854(17) 0.0199(6) Uani 1 1 d . U . . .
S2 S 0.38517(6) 0.4744(4) 0.74530(18) 0.0294(7) Uani 1 1 d . 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
C1 C2 1.365(10) . ?
C1 C7 1.436(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.426(10) 7 ?
C2 H2 0.9300 . ?
C3 C4 1.371(10) . ?
C3 C2 1.426(10) 7 ?
C3 C5 1.463(10) 7 ?
C4 C5 1.418(11) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(10) . ?
C5 C3 1.463(10) 7 ?
C6 C7 1.386(10) . ?
C6 H6 0.9300 . ?
C7 C8 1.454(11) . ?
C8 C9 1.351(11) . ?
C8 S1 1.770(8) . ?
C9 C10 1.435(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.449(10) . ?
C11 S1 1.727(8) . ?
C12 C13 1.366(11) . ?
C12 S2 1.727(8) . ?
C13 C14 1.436(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.345(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.503(11) . ?
C15 S2 1.727(9) . ?
C16 C20 1.338(18) . ?
C16 C17 1.418(17) . ?
C16 H23 0.9700 . ?
C16 H24 0.9700 . ?
C16 H25 0.9700 . ?
C16 H26 0.9700 . ?
C17 C18 1.59(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.55(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.55(2) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.51(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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 C7 121.1(7) . . ?
C2 C1 H1 119.4 . . ?
C7 C1 H1 119.4 . . ?
C1 C2 C3 122.3(7) . 7 ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 7 . ?
C4 C3 C2 124.7(7) . 7 ?
C4 C3 C5 119.1(7) . 7 ?
C2 C3 C5 116.1(7) 7 7 ?
C3 C4 C5 124.3(7) . . ?
C3 C4 H4 117.8 . . ?
C5 C4 H4 117.8 . . ?
C6 C5 C4 123.0(8) . . ?
C6 C5 C3 120.5(7) . 7 ?
C4 C5 C3 116.5(7) . 7 ?
C7 C6 C5 121.4(8) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C1 118.5(7) . . ?
C6 C7 C8 120.7(7) . . ?
C1 C7 C8 120.8(7) . . ?
C9 C8 C7 130.1(8) . . ?
C9 C8 S1 109.6(6) . . ?
C7 C8 S1 120.3(6) . . ?
C8 C9 C10 115.3(8) . . ?
C8 C9 H9 122.4 . . ?
C10 C9 H9 122.4 . . ?
C11 C10 C9 111.5(7) . . ?
C11 C10 H10 124.3 . . ?
C9 C10 H10 124.3 . . ?
C10 C11 C12 127.0(7) . . ?
C10 C11 S1 111.3(6) . . ?
C12 C11 S1 121.5(6) . . ?
C13 C12 C11 129.2(7) . . ?
C13 C12 S2 110.0(6) . . ?
C11 C12 S2 120.8(6) . . ?
C12 C13 C14 113.5(8) . . ?
C12 C13 H13 123.2 . . ?
C14 C13 H13 123.2 . . ?
C15 C14 C13 112.5(8) . . ?
C15 C14 H14 123.8 . . ?
C13 C14 H14 123.8 . . ?
C14 C15 C16 129.0(8) . . ?
C14 C15 S2 111.5(7) . . ?
C16 C15 S2 119.3(7) . . ?
C20 C16 C15 122.7(11) . . ?
C17 C16 C15 118.7(11) . . ?
C17 C16 H23 107.6 . . ?
C15 C16 H23 107.6 . . ?
C17 C16 H24 107.6 . . ?
C15 C16 H24 107.6 . . ?
H23 C16 H24 107.1 . . ?
C20 C16 H25 106.7 . . ?
C15 C16 H25 106.7 . . ?
C20 C16 H26 106.7 . . ?
C15 C16 H26 106.7 . . ?
H25 C16 H26 106.6 . . ?
C16 C17 C18 112.8(14) . . ?
C16 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C19 C18 C17 110.7(15) . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 C21 115.6(14) . . ?
C16 C20 H20A 108.4 . . ?
C21 C20 H20A 108.4 . . ?
C16 C20 H20B 108.4 . . ?
C21 C20 H20B 108.4 . . ?
H20A C20 H20B 107.4 . . ?
C22 C21 C20 115.7(15) . . ?
C22 C21 H21A 108.4 . . ?
C20 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C20 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 S1 C8 92.4(4) . . ?
C15 S2 C12 92.5(4) . . ?

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
C7 C1 C2 C3 0.3(12) . . . 7 ?
C2 C3 C4 C5 178.6(8) 7 . . . ?
C5 C3 C4 C5 1.6(13) 7 . . . ?
C3 C4 C5 C6 177.3(7) . . . . ?
C3 C4 C5 C3 -1.6(13) . . . 7 ?
C4 C5 C6 C7 -177.1(8) . . . . ?
C3 C5 C6 C7 1.7(12) 7 . . . ?
C5 C6 C7 C1 -2.3(11) . . . . ?
C5 C6 C7 C8 177.6(7) . . . . ?
C2 C1 C7 C6 1.3(11) . . . . ?
C2 C1 C7 C8 -178.6(7) . . . . ?
C6 C7 C8 C9 -0.9(13) . . . . ?
C1 C7 C8 C9 179.0(8) . . . . ?
C6 C7 C8 S1 -177.8(6) . . . . ?
C1 C7 C8 S1 2.1(10) . . . . ?
C7 C8 C9 C10 -178.8(8) . . . . ?
S1 C8 C9 C10 -1.6(9) . . . . ?
C8 C9 C10 C11 1.0(10) . . . . ?
C9 C10 C11 C12 -175.2(7) . . . . ?
C9 C10 C11 S1 0.1(9) . . . . ?
C10 C11 C12 C13 179.0(9) . . . . ?
S1 C11 C12 C13 4.1(12) . . . . ?
C10 C11 C12 S2 2.3(12) . . . . ?
S1 C11 C12 S2 -172.6(5) . . . . ?
C11 C12 C13 C14 -177.7(8) . . . . ?
S2 C12 C13 C14 -0.6(10) . . . . ?
C12 C13 C14 C15 0.0(11) . . . . ?
C13 C14 C15 C16 175.4(8) . . . . ?
C13 C14 C15 S2 0.6(10) . . . . ?
C14 C15 C16 C20 116.6(14) . . . . ?
S2 C15 C16 C20 -68.9(14) . . . . ?
C14 C15 C16 C17 26.3(17) . . . . ?
S2 C15 C16 C17 -159.2(11) . . . . ?
C15 C16 C17 C18 174.7(11) . . . . ?
C16 C17 C18 C19 172.0(14) . . . . ?
C15 C16 C20 C21 -162.6(12) . . . . ?
C16 C20 C21 C22 -173.6(15) . . . . ?
C10 C11 S1 C8 -0.9(6) . . . . ?
C12 C11 S1 C8 174.8(7) . . . . ?
C9 C8 S1 C11 1.4(7) . . . . ?
C7 C8 S1 C11 178.9(7) . . . . ?
C14 C15 S2 C12 -0.8(7) . . . . ?
C16 C15 S2 C12 -176.2(7) . . . . ?
C13 C12 S2 C15 0.8(7) . . . . ?
C11 C12 S2 C15 178.1(7) . . . . ?

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_C6DBTA
_database_code_depnum_ccdc_archive 'CCDC 1956922'
loop_
_audit_author_name
_audit_author_address
'Naoki Aratani'
;Nara Institute of Science and Technology
Japan
;
_audit_update_record             
;
2019-10-01 deposited with the CCDC.	2020-01-13 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         'C42 H42 S4'
_chemical_formula_sum            'C42 H42 S4'
_chemical_formula_weight         674.99

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'
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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   23.82(3)
_cell_length_b                   5.837(6)
_cell_length_c                   12.500(14)
_cell_angle_alpha                90
_cell_angle_beta                 104.133(18)
_cell_angle_gamma                90
_cell_volume                     1685(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    90
_cell_measurement_reflns_used    426
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      20.39

_exptl_crystal_description       prism

_exptl_crystal_colour            yellow

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             716
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.313
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            6554
_diffrn_reflns_av_unetI/netI     0.1766
_diffrn_reflns_av_R_equivalents  0.1576
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.763
_diffrn_reflns_theta_max         23.500
_diffrn_reflns_theta_full        23.500
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2474
_reflns_number_gt                1407
_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       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'

_diffrn_radiation_source         'fine-focus sealed tube'


_diffrn_radiation_monochromator  graphite

_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_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)+(0.0628P)²+19.6410P] 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         2474
_refine_ls_number_parameters     209
_refine_ls_number_restraints     168
_refine_ls_R_factor_all          0.1864
_refine_ls_R_factor_gt           0.1165
_refine_ls_wR_factor_ref         0.2799
_refine_ls_wR_factor_gt          0.2407
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.061
_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
C1 C 0.4196(4) 0.2050(16) 0.0650(7) 0.019(2) Uani 1 1 d . U . . .
H1 H 0.4111 0.0586 0.0319 0.023 Uiso 1 1 calc R U . . .
C2 C 0.3923(4) 0.2755(15) 0.1442(7) 0.018(2) Uani 1 1 d . U . . .
H2 H 0.3649 0.1766 0.1645 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4040(4) 0.4966(16) 0.1974(7) 0.018(2) Uani 1 1 d . U . . .
C4 C 0.4450(4) 0.6331(17) 0.1685(7) 0.015(2) Uani 1 1 d . U . . .
H4 H 0.4545 0.7753 0.2055 0.019 Uiso 1 1 calc R U . . .
C5 C 0.4738(4) 0.5713(16) 0.0862(8) 0.018(2) Uani 1 1 d . U . . .
C6 C 0.5134(4) 0.7139(16) 0.0515(7) 0.019(2) Uani 1 1 d . U . . .
H6 H 0.5227 0.8580 0.0867 0.023 Uiso 1 1 calc R U . . .
C7 C 0.5398(4) 0.6526(16) -0.0326(7) 0.018(2) Uani 1 1 d . U . . .
C8 C 0.3730(4) 0.5685(16) 0.2786(7) 0.019(2) Uani 1 1 d . U . . .
C9 C 0.3788(4) 0.7689(16) 0.3381(7) 0.019(2) Uani 1 1 d . U . . .
H9 H 0.4055 0.8863 0.3322 0.022 Uiso 1 1 calc R U . . .
C10 C 0.3406(4) 0.7821(16) 0.4094(7) 0.018(2) Uani 1 1 d . U . . .
H10 H 0.3391 0.9107 0.4552 0.022 Uiso 1 1 calc R U . . .
C11 C 0.3063(4) 0.5932(16) 0.4063(7) 0.019(2) Uani 1 1 d . U . . .
C12 C 0.2662(5) 0.5344(16) 0.4726(7) 0.020(2) Uani 1 1 d . U . . .
C13 C 0.2361(5) 0.3371(17) 0.4732(8) 0.022(2) Uani 1 1 d . U . . .
H13 H 0.2369 0.2150 0.4234 0.027 Uiso 1 1 calc R U . . .
C14 C 0.2033(5) 0.3265(17) 0.5535(8) 0.023(2) Uani 1 1 d . U . . .
H14 H 0.1805 0.1987 0.5638 0.028 Uiso 1 1 calc R U . . .
C15 C 0.2087(5) 0.5276(17) 0.6154(7) 0.022(2) Uani 1 1 d . U . . .
C16 C 0.1825(5) 0.5772(17) 0.7114(8) 0.027(2) Uani 1 1 d . U . . .
H16A H 0.2138 0.5716 0.7800 0.033 Uiso 1 1 calc R U . . .
H16B H 0.1549 0.4527 0.7158 0.033 Uiso 1 1 calc R U . . .
C17 C 0.1509(5) 0.8050(17) 0.7086(8) 0.029(2) Uani 1 1 d . U . . .
H17A H 0.1794 0.9316 0.7191 0.035 Uiso 1 1 calc R U . . .
H17B H 0.1238 0.8247 0.6354 0.035 Uiso 1 1 calc R U . . .
C18 C 0.1175(5) 0.8181(17) 0.7975(8) 0.029(2) Uani 1 1 d . U . . .
H18A H 0.1440 0.7752 0.8688 0.035 Uiso 1 1 calc R U . . .
H18B H 0.0861 0.7029 0.7807 0.035 Uiso 1 1 calc R U . . .
C19 C 0.0909(5) 1.0509(18) 0.8110(8) 0.033(3) Uani 1 1 d . U . . .
H19A H 0.0665 1.1002 0.7388 0.040 Uiso 1 1 calc R U . . .
H19B H 0.1224 1.1648 0.8341 0.040 Uiso 1 1 calc R U . . .
C20 C 0.0542(5) 1.0477(18) 0.8956(8) 0.032(3) Uani 1 1 d . U . . .
H20A H 0.0200 0.9489 0.8680 0.038 Uiso 1 1 calc R U . . .
H20B H 0.0772 0.9809 0.9654 0.038 Uiso 1 1 calc R U . . .
C21 C 0.0342(6) 1.287(2) 0.9179(10) 0.045(3) Uani 1 1 d . U . . .
H21A H 0.0680 1.3817 0.9513 0.067 Uiso 1 1 calc R U . . .
H21B H 0.0087 1.2770 0.9684 0.067 Uiso 1 1 calc R U . . .
H21C H 0.0132 1.3570 0.8483 0.067 Uiso 1 1 calc R U . . .
S1 S 0.32011(12) 0.3962(4) 0.3114(2) 0.0211(7) Uani 1 1 d . U . . .
S2 S 0.25500(13) 0.7202(4) 0.5741(2) 0.0249(8) Uani 1 1 d . 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
C1 C2 1.374(13) . ?
C1 C7 1.407(13) 3_665 ?
C1 H1 0.9500 . ?
C2 C3 1.448(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(13) . ?
C3 C8 1.454(13) . ?
C4 C5 1.414(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(14) . ?
C5 C7 1.469(13) 3_665 ?
C6 C7 1.397(13) . ?
C6 H6 0.9500 . ?
C7 C1 1.407(13) 3_665 ?
C7 C5 1.469(13) 3_665 ?
C8 C9 1.374(13) . ?
C8 S1 1.738(10) . ?
C9 C10 1.423(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.368(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.450(14) . ?
C11 S1 1.740(9) . ?
C12 C13 1.359(14) . ?
C12 S2 1.738(9) . ?
C13 C14 1.415(14) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(14) . ?
C14 H14 0.9500 . ?
C15 C16 1.510(13) . ?
C15 S2 1.739(10) . ?
C16 C17 1.524(14) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.518(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.526(14) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.527(15) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.525(15) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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 C7 120.7(9) . 3_665 ?
C2 C1 H1 119.6 . . ?
C7 C1 H1 119.6 3_665 . ?
C1 C2 C3 121.7(9) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C4 C3 C2 117.7(9) . . ?
C4 C3 C8 122.0(8) . . ?
C2 C3 C8 120.3(9) . . ?
C3 C4 C5 123.0(9) . . ?
C3 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C6 C5 C4 123.7(9) . . ?
C6 C5 C7 118.4(9) . 3_665 ?
C4 C5 C7 117.8(9) . 3_665 ?
C7 C6 C5 122.7(9) . . ?
C7 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
C6 C7 C1 122.2(8) . 3_665 ?
C6 C7 C5 118.8(9) . 3_665 ?
C1 C7 C5 119.0(9) 3_665 3_665 ?
C9 C8 C3 128.5(9) . . ?
C9 C8 S1 110.4(7) . . ?
C3 C8 S1 121.2(7) . . ?
C8 C9 C10 112.9(9) . . ?
C8 C9 H9 123.5 . . ?
C10 C9 H9 123.5 . . ?
C11 C10 C9 114.1(9) . . ?
C11 C10 H10 123.0 . . ?
C9 C10 H10 123.0 . . ?
C10 C11 C12 130.3(8) . . ?
C10 C11 S1 109.9(7) . . ?
C12 C11 S1 119.6(7) . . ?
C13 C12 C11 128.8(8) . . ?
C13 C12 S2 110.4(7) . . ?
C11 C12 S2 120.6(7) . . ?
C12 C13 C14 115.1(9) . . ?
C12 C13 H13 122.4 . . ?
C14 C13 H13 122.4 . . ?
C15 C14 C13 111.4(9) . . ?
C15 C14 H14 124.3 . . ?
C13 C14 H14 124.3 . . ?
C14 C15 C16 127.0(9) . . ?
C14 C15 S2 111.0(7) . . ?
C16 C15 S2 121.9(7) . . ?
C15 C16 C17 116.5(8) . . ?
C15 C16 H16A 108.2 . . ?
C17 C16 H16A 108.2 . . ?
C15 C16 H16B 108.2 . . ?
C17 C16 H16B 108.2 . . ?
H16A C16 H16B 107.3 . . ?
C18 C17 C16 111.8(8) . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 C19 115.6(9) . . ?
C17 C18 H18A 108.4 . . ?
C19 C18 H18A 108.4 . . ?
C17 C18 H18B 108.4 . . ?
C19 C18 H18B 108.4 . . ?
H18A C18 H18B 107.4 . . ?
C18 C19 C20 112.9(9) . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 111.9(9) . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C8 S1 C11 92.7(5) . . ?
C12 S2 C15 92.0(5) . . ?

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
C7 C1 C2 C3 -0.3(14) 3_665 . . . ?
C1 C2 C3 C4 -1.9(14) . . . . ?
C1 C2 C3 C8 178.3(9) . . . . ?
C2 C3 C4 C5 3.1(14) . . . . ?
C8 C3 C4 C5 -177.1(9) . . . . ?
C3 C4 C5 C6 176.4(9) . . . . ?
C3 C4 C5 C7 -2.1(14) . . . 3_665 ?
C4 C5 C6 C7 -177.7(9) . . . . ?
C7 C5 C6 C7 0.8(15) 3_665 . . . ?
C5 C6 C7 C1 -178.7(9) . . . 3_665 ?
C5 C6 C7 C5 -0.8(16) . . . 3_665 ?
C4 C3 C8 C9 -0.7(16) . . . . ?
C2 C3 C8 C9 179.1(9) . . . . ?
C4 C3 C8 S1 178.4(7) . . . . ?
C2 C3 C8 S1 -1.7(12) . . . . ?
C3 C8 C9 C10 179.2(9) . . . . ?
S1 C8 C9 C10 0.0(11) . . . . ?
C8 C9 C10 C11 0.8(12) . . . . ?
C9 C10 C11 C12 174.0(10) . . . . ?
C9 C10 C11 S1 -1.2(11) . . . . ?
C10 C11 C12 C13 -174.3(11) . . . . ?
S1 C11 C12 C13 0.5(14) . . . . ?
C10 C11 C12 S2 1.1(15) . . . . ?
S1 C11 C12 S2 175.9(5) . . . . ?
C11 C12 C13 C14 175.8(10) . . . . ?
S2 C12 C13 C14 0.0(12) . . . . ?
C12 C13 C14 C15 0.7(13) . . . . ?
C13 C14 C15 C16 -177.1(10) . . . . ?
C13 C14 C15 S2 -1.0(11) . . . . ?
C14 C15 C16 C17 -131.7(11) . . . . ?
S2 C15 C16 C17 52.6(13) . . . . ?
C15 C16 C17 C18 169.9(10) . . . . ?
C16 C17 C18 C19 172.4(10) . . . . ?
C17 C18 C19 C20 175.7(10) . . . . ?
C18 C19 C20 C21 173.1(10) . . . . ?
C9 C8 S1 C11 -0.5(8) . . . . ?
C3 C8 S1 C11 -179.9(8) . . . . ?
C10 C11 S1 C8 1.0(8) . . . . ?
C12 C11 S1 C8 -174.8(8) . . . . ?
C13 C12 S2 C15 -0.5(8) . . . . ?
C11 C12 S2 C15 -176.7(8) . . . . ?
C14 C15 S2 C12 0.9(8) . . . . ?
C16 C15 S2 C12 177.2(9) . . . . ?

_refine_diff_density_max         1.145
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.124

####################################################################### 
# 
# 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_EBDBTA
_database_code_depnum_ccdc_archive 'CCDC 1956923'
loop_
_audit_author_name
_audit_author_address
'Naoki Aratani'
;Nara Institute of Science and Technology
Japan
;
_audit_update_record             
;
2019-10-01 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C42 H42 S4'
_chemical_formula_moiety         'C42 H42 S4'
_chemical_formula_weight         675.03
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   22.150(3)
_cell_length_b                   5.7413(7)
_cell_length_c                   13.1188(16)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.850(7)
_cell_angle_gamma                90.0000
_cell_volume                     1659.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8439
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      25.41
_cell_measurement_temperature    103
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716.00
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.331
_exptl_absorpt_correction_T_max  0.997

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      103
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            20577
_diffrn_reflns_av_R_equivalents  0.1552
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.122
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3019
_reflns_number_gt                2053
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1411
_refine_ls_R_factor_gt           0.0965
_refine_ls_wR_factor_ref         0.2772
_refine_ls_wR_factor_gt          0.2486
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3019
_refine_ls_number_parameters     210
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1557P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.53
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.31493(7) 0.6074(3) 0.58857(11) 0.0428(5) Uani 1 1 d . . . . .
S2 S 0.25453(7) 0.2991(3) 0.29077(11) 0.0445(5) Uani 1 1 d . . . . .
C1 C 0.4145(3) 0.7933(11) 0.8874(4) 0.0447(15) Uani 1 1 d . . . . .
H1 H 0.4049 0.9416 0.9135 0.054 Uiso 1 1 calc R U . . .
C2 C 0.3865(3) 0.7217(10) 0.7959(4) 0.0433(15) Uani 1 1 d . . . . .
H2 H 0.3569 0.8192 0.7600 0.052 Uiso 1 1 calc R U . . .
C3 C 0.4009(3) 0.5001(11) 0.7519(4) 0.0408(14) Uani 1 1 d . . . . .
C4 C 0.4446(3) 0.3630(11) 0.8036(4) 0.0448(15) Uani 1 1 d . . . . .
H4 H 0.4560 0.2211 0.7736 0.054 Uiso 1 1 calc R U . . .
C5 C 0.4734(3) 0.4303(10) 0.9022(4) 0.0406(14) Uani 1 1 d . . . . .
C6 C 0.5152(3) 0.2855(10) 0.9590(4) 0.0398(14) Uani 1 1 d . . . . .
H6 H 0.5254 0.1394 0.9313 0.048 Uiso 1 1 calc R U . . .
C7 C 0.5418(3) 0.3514(10) 1.0546(4) 0.0393(14) Uani 1 1 d . . . . .
C8 C 0.3700(3) 0.4283(11) 0.6535(4) 0.0415(15) Uani 1 1 d . . . . .
C9 C 0.3761(3) 0.2303(10) 0.5986(4) 0.0407(14) Uani 1 1 d . . . . .
H9 H 0.4037 0.1095 0.6207 0.049 Uiso 1 1 calc R U . . .
C10 C 0.3377(3) 0.2197(11) 0.5053(4) 0.0414(14) Uani 1 1 d . . . . .
H10 H 0.3365 0.0907 0.4598 0.050 Uiso 1 1 calc R U . . .
C11 C 0.3025(3) 0.4147(10) 0.4874(4) 0.0400(14) Uani 1 1 d . . . . .
C12 C 0.2623(3) 0.4752(11) 0.3988(4) 0.0403(14) Uani 1 1 d . . . . .
C13 C 0.2295(3) 0.6728(11) 0.3805(4) 0.0467(16) Uani 1 1 d . . . . .
H13 H 0.2286 0.7950 0.4291 0.056 Uiso 1 1 calc R U . . .
C14 C 0.1966(3) 0.6800(11) 0.2823(4) 0.0465(15) Uani 1 1 d . . . . .
H14 H 0.1704 0.8051 0.2600 0.056 Uiso 1 1 calc R U . . .
C15 C 0.2055(3) 0.4962(11) 0.2239(4) 0.0441(15) Uani 1 1 d . . . . .
C16 C 0.1811(3) 0.4472(11) 0.1150(4) 0.0473(16) Uani 1 1 d . . . . .
H16A H 0.2159 0.4305 0.0740 0.057 Uiso 1 1 calc R U . . .
H16B H 0.1576 0.5849 0.0885 0.057 Uiso 1 1 calc R U . . .
C17 C 0.1404(3) 0.2303(11) 0.0962(4) 0.0479(16) Uani 1 1 d . . . . .
H17 H 0.1666 0.0905 0.1118 0.058 Uiso 1 1 calc R U . . .
C18 C 0.1171(3) 0.2192(12) -0.0181(4) 0.0506(16) Uani 1 1 d . . . . .
H18A H 0.0893 0.3521 -0.0347 0.061 Uiso 1 1 calc R U . . .
H18B H 0.1519 0.2365 -0.0590 0.061 Uiso 1 1 calc R U . . .
C19 C 0.0837(3) -0.0062(13) -0.0494(5) 0.0568(17) Uani 1 1 d . . . . .
H19A H 0.0471 -0.0185 -0.0136 0.068 Uiso 1 1 calc R U . . .
H19B H 0.1103 -0.1393 -0.0312 0.068 Uiso 1 1 calc R U . . .
H19C H 0.0723 -0.0055 -0.1236 0.068 Uiso 1 1 calc R U . . .
C20 C 0.0896(3) 0.2216(11) 0.1670(4) 0.0493(16) Uani 1 1 d . . . . .
H20A H 0.0679 0.0716 0.1558 0.059 Uiso 1 1 calc R U . . .
H20B H 0.1083 0.2233 0.2388 0.059 Uiso 1 1 calc R U . . .
C21 C 0.0433(3) 0.4181(13) 0.1535(5) 0.0599(19) Uani 1 1 d . . . . .
H21A H 0.0210 0.4081 0.0852 0.072 Uiso 1 1 calc R U . . .
H21B H 0.0642 0.5684 0.1611 0.072 Uiso 1 1 calc R U . . .
H21C H 0.0147 0.4041 0.2056 0.072 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# 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
S1 C11 1.728(6) . ?
S1 C8 1.749(6) . ?
S2 C12 1.736(6) . ?
S2 C15 1.743(6) . ?
C1 C2 1.357(8) . ?
C1 C7 1.434(8) 3_667 ?
C1 H1 0.9500 . ?
C2 C3 1.446(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(8) . ?
C3 C8 1.458(8) . ?
C4 C5 1.435(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(8) . ?
C5 C7 1.430(8) 3_667 ?
C6 C7 1.384(8) . ?
C6 H6 0.9500 . ?
C7 C5 1.430(8) 3_667 ?
C7 C1 1.434(8) 3_667 ?
C8 C9 1.360(8) . ?
C9 C10 1.418(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.432(7) . ?
C12 C13 1.356(8) . ?
C13 C14 1.415(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.331(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.501(8) . ?
C16 C17 1.542(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C20 1.530(8) . ?
C17 C18 1.536(8) . ?
C17 H17 1.0000 . ?
C18 C19 1.525(9) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.524(9) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C11 S1 C8 92.6(3) . . ?
C12 S2 C15 92.2(3) . . ?
C2 C1 C7 121.1(6) . 3_667 ?
C2 C1 H1 119.4 . . ?
C7 C1 H1 119.4 3_667 . ?
C1 C2 C3 121.3(6) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 118.7(5) . . ?
C4 C3 C8 121.3(6) . . ?
C2 C3 C8 120.0(5) . . ?
C3 C4 C5 121.1(6) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C7 118.6(5) . 3_667 ?
C6 C5 C4 121.9(6) . . ?
C7 C5 C4 119.5(5) 3_667 . ?
C7 C6 C5 121.2(5) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C5 120.2(5) . 3_667 ?
C6 C7 C1 121.7(5) . 3_667 ?
C5 C7 C1 118.1(5) 3_667 3_667 ?
C9 C8 C3 129.9(6) . . ?
C9 C8 S1 109.6(4) . . ?
C3 C8 S1 120.4(5) . . ?
C8 C9 C10 114.1(5) . . ?
C8 C9 H9 122.9 . . ?
C10 C9 H9 122.9 . . ?
C11 C10 C9 113.2(5) . . ?
C11 C10 H10 123.4 . . ?
C9 C10 H10 123.4 . . ?
C10 C11 C12 129.2(5) . . ?
C10 C11 S1 110.4(4) . . ?
C12 C11 S1 120.3(4) . . ?
C13 C12 C11 128.6(5) . . ?
C13 C12 S2 109.6(4) . . ?
C11 C12 S2 121.6(5) . . ?
C12 C13 C14 113.8(5) . . ?
C12 C13 H13 123.1 . . ?
C14 C13 H13 123.1 . . ?
C15 C14 C13 114.1(6) . . ?
C15 C14 H14 122.9 . . ?
C13 C14 H14 122.9 . . ?
C14 C15 C16 129.5(6) . . ?
C14 C15 S2 110.3(4) . . ?
C16 C15 S2 120.2(5) . . ?
C15 C16 C17 116.9(5) . . ?
C15 C16 H16A 108.1 . . ?
C17 C16 H16A 108.1 . . ?
C15 C16 H16B 108.1 . . ?
C17 C16 H16B 108.1 . . ?
H16A C16 H16B 107.3 . . ?
C20 C17 C18 113.3(5) . . ?
C20 C17 C16 112.5(5) . . ?
C18 C17 C16 108.8(5) . . ?
C20 C17 H17 107.3 . . ?
C18 C17 H17 107.3 . . ?
C16 C17 H17 107.3 . . ?
C19 C18 C17 113.8(6) . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C17 115.7(5) . . ?
C21 C20 H20A 108.4 . . ?
C17 C20 H20A 108.4 . . ?
C21 C20 H20B 108.4 . . ?
C17 C20 H20B 108.4 . . ?
H20A C20 H20B 107.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C7 C1 C2 C3 -1.8(9) 3_667 . . . ?
C1 C2 C3 C4 -1.2(9) . . . . ?
C1 C2 C3 C8 179.9(5) . . . . ?
C2 C3 C4 C5 3.5(9) . . . . ?
C8 C3 C4 C5 -177.7(5) . . . . ?
C3 C4 C5 C6 175.7(6) . . . . ?
C3 C4 C5 C7 -2.8(9) . . . 3_667 ?
C7 C5 C6 C7 -0.5(9) 3_667 . . . ?
C4 C5 C6 C7 -179.0(5) . . . . ?
C5 C6 C7 C5 0.5(10) . . . 3_667 ?
C5 C6 C7 C1 -178.7(5) . . . 3_667 ?
C4 C3 C8 C9 1.3(10) . . . . ?
C2 C3 C8 C9 -179.9(6) . . . . ?
C4 C3 C8 S1 -179.4(5) . . . . ?
C2 C3 C8 S1 -0.6(7) . . . . ?
C11 S1 C8 C9 -1.2(5) . . . . ?
C11 S1 C8 C3 179.4(5) . . . . ?
C3 C8 C9 C10 179.6(6) . . . . ?
S1 C8 C9 C10 0.2(6) . . . . ?
C8 C9 C10 C11 1.3(7) . . . . ?
C9 C10 C11 C12 174.5(6) . . . . ?
C9 C10 C11 S1 -2.1(6) . . . . ?
C8 S1 C11 C10 1.9(5) . . . . ?
C8 S1 C11 C12 -175.0(5) . . . . ?
C10 C11 C12 C13 -177.2(6) . . . . ?
S1 C11 C12 C13 -0.9(9) . . . . ?
C10 C11 C12 S2 -2.8(9) . . . . ?
S1 C11 C12 S2 173.5(3) . . . . ?
C15 S2 C12 C13 -1.0(5) . . . . ?
C15 S2 C12 C11 -176.4(5) . . . . ?
C11 C12 C13 C14 177.1(6) . . . . ?
S2 C12 C13 C14 2.1(7) . . . . ?
C12 C13 C14 C15 -2.5(8) . . . . ?
C13 C14 C15 C16 -177.0(6) . . . . ?
C13 C14 C15 S2 1.6(7) . . . . ?
C12 S2 C15 C14 -0.3(5) . . . . ?
C12 S2 C15 C16 178.4(5) . . . . ?
C14 C15 C16 C17 -118.3(7) . . . . ?
S2 C15 C16 C17 63.3(7) . . . . ?
C15 C16 C17 C20 50.1(7) . . . . ?
C15 C16 C17 C18 176.6(5) . . . . ?
C20 C17 C18 C19 -62.4(7) . . . . ?
C16 C17 C18 C19 171.6(5) . . . . ?
C18 C17 C20 C21 -60.3(7) . . . . ?
C16 C17 C20 C21 63.7(7) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


