# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2127997'
loop_
_audit_author_name
_audit_author_address
'Masahiro Hayakawa'
;Department of Chemistry, Graduate School of Science, Nagoya University
Japan
;
_audit_update_record             
;
2021-12-12 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            TN-Ant
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 S2'
_chemical_formula_weight         374.53

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                   17.5384(3)
_cell_length_b                   11.5092(2)
_cell_length_c                   9.5134(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.451(2)
_cell_angle_gamma                90
_cell_volume                     1875.14(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    20110
_cell_measurement_theta_min      2.3240
_cell_measurement_theta_max      30.8540

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.289
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77528
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku Saturn70 (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24314
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.132
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4257
_reflns_number_gt                3914
_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       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_reduction        
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0571P)²+0.4912P] 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         4257
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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
S001 S 0.26945(2) 0.30404(3) 0.71518(4) 0.03037(10) Uani 1 1 d . . . . .
S002 S 0.11491(2) 0.25108(3) 0.78856(4) 0.03422(11) Uani 1 1 d . . . . .
C003 C 0.55771(7) 0.48177(9) 0.71148(12) 0.0232(2) Uani 1 1 d . . . . .
C004 C 0.50919(7) 0.39289(9) 0.63163(12) 0.0223(2) Uani 1 1 d . . . . .
C005 C 0.53880(7) 0.32674(10) 0.53208(12) 0.0233(2) Uani 1 1 d . . . . .
H005 H 0.506654 0.269057 0.477425 0.028 Uiso 1 1 calc R U . . .
C006 C 0.61456(7) 0.34343(10) 0.51106(12) 0.0235(2) Uani 1 1 d . . . . .
C007 C 0.66291(7) 0.43190(10) 0.59229(12) 0.0249(2) Uani 1 1 d . . . . .
C008 C 0.63302(7) 0.49884(10) 0.69006(12) 0.0255(2) Uani 1 1 d . . . . .
H008 H 0.664794 0.557539 0.743395 0.031 Uiso 1 1 calc R U . . .
C009 C 0.40551(7) 0.43863(10) 0.75866(12) 0.0244(2) Uani 1 1 d . . . . .
C00A C 0.43332(7) 0.37447(10) 0.65819(12) 0.0240(2) Uani 1 1 d . . . . .
H00A H 0.400920 0.316277 0.605141 0.029 Uiso 1 1 calc R U . . .
C00B C 0.07055(7) 0.56174(11) 0.77768(14) 0.0292(3) Uani 1 1 d . . . . .
H00B H 0.101613 0.527982 0.712356 0.035 Uiso 1 1 calc R U . . .
H00C H 0.045822 0.633750 0.732361 0.035 Uiso 1 1 calc R U . . .
C00C C 0.52601(7) 0.54970(10) 0.81095(12) 0.0273(2) Uani 1 1 d . . . . .
H00D H 0.556584 0.610306 0.862677 0.033 Uiso 1 1 calc R U . . .
C00D C 0.64525(7) 0.27681(11) 0.40928(13) 0.0281(2) Uani 1 1 d . . . . .
H00E H 0.613911 0.218193 0.354867 0.034 Uiso 1 1 calc R U . . .
C00E C 0.45357(7) 0.52979(11) 0.83319(12) 0.0273(2) Uani 1 1 d . . . . .
H00F H 0.434140 0.577079 0.899455 0.033 Uiso 1 1 calc R U . . .
C00F C 0.71875(8) 0.29600(12) 0.38902(14) 0.0322(3) Uani 1 1 d . . . . .
H00G H 0.738132 0.250971 0.320646 0.039 Uiso 1 1 calc R U . . .
C00G C 0.29485(7) 0.47564(11) 0.88862(13) 0.0284(3) Uani 1 1 d . . . . .
H00H H 0.318704 0.540503 0.942487 0.034 Uiso 1 1 calc R U . . .
C00H C 0.32931(7) 0.41651(10) 0.79316(13) 0.0257(2) Uani 1 1 d . . . . .
C00I C -0.01704(8) 0.39114(12) 0.66758(15) 0.0330(3) Uani 1 1 d . . . . .
H00I H -0.041138 0.436187 0.580686 0.040 Uiso 1 1 calc R U . . .
H00J H -0.057354 0.337727 0.688799 0.040 Uiso 1 1 calc R U . . .
C00J C 0.12549(8) 0.59301(12) 0.92028(15) 0.0332(3) Uani 1 1 d . . . . .
H00K H 0.094494 0.626507 0.985894 0.040 Uiso 1 1 calc R U . . .
H00L H 0.162534 0.653321 0.902453 0.040 Uiso 1 1 calc R U . . .
C00K C 0.00624(7) 0.47537(11) 0.79347(14) 0.0307(3) Uani 1 1 d . . . . .
H00M H 0.024313 0.429938 0.882810 0.037 Uiso 1 1 calc R U . . .
H00N H -0.040574 0.519628 0.804195 0.037 Uiso 1 1 calc R U . . .
C00L C 0.76662(8) 0.38311(12) 0.46973(14) 0.0333(3) Uani 1 1 d . . . . .
H00O H 0.817845 0.395613 0.454900 0.040 Uiso 1 1 calc R U . . .
C00M C 0.19892(7) 0.33783(11) 0.81169(14) 0.0291(3) Uani 1 1 d . . . . .
C00N C 0.73992(7) 0.44893(11) 0.56812(13) 0.0302(3) Uani 1 1 d . . . . .
H00P H 0.772738 0.506665 0.621187 0.036 Uiso 1 1 calc R U . . .
C00O C 0.22067(7) 0.43191(11) 0.90025(13) 0.0283(3) Uani 1 1 d . . . . .
C00P C 0.17209(8) 0.48829(13) 0.99459(13) 0.0335(3) Uani 1 1 d . . . . .
H00Q H 0.206801 0.514357 1.085390 0.040 Uiso 1 1 calc R U . . .
H00R H 0.135390 0.430231 1.019154 0.040 Uiso 1 1 calc R U . . .
C00Q C 0.04969(8) 0.31837(12) 0.63318(14) 0.0337(3) Uani 1 1 d . . . . .
H00S H 0.081342 0.368665 0.583461 0.040 Uiso 1 1 calc R U . . .
H00T H 0.026872 0.256153 0.565149 0.040 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C00H 1.7299(12) . ?
S001 C00M 1.7360(13) . ?
S002 C00M 1.7539(13) . ?
S002 C00Q 1.8341(15) . ?
C003 C008 1.3932(17) . ?
C003 C00C 1.4292(17) . ?
C003 C004 1.4384(15) . ?
C004 C005 1.3994(16) . ?
C004 C00A 1.4228(16) . ?
C005 C006 1.3989(16) . ?
C006 C00D 1.4283(17) . ?
C006 C007 1.4389(16) . ?
C007 C008 1.3942(17) . ?
C007 C00N 1.4315(17) . ?
C009 C00A 1.3775(16) . ?
C009 C00E 1.4341(16) . ?
C009 C00H 1.4654(17) . ?
C00B C00J 1.5280(18) . ?
C00B C00K 1.5349(17) . ?
C00C C00E 1.3517(18) . ?
C00D C00F 1.3619(18) . ?
C00F C00L 1.4218(19) . ?
C00G C00H 1.3747(17) . ?
C00G C00O 1.4214(18) . ?
C00I C00K 1.5264(18) . ?
C00I C00Q 1.5309(19) . ?
C00J C00P 1.5399(19) . ?
C00L C00N 1.3632(19) . ?
C00M C00O 1.3745(18) . ?
C00O C00P 1.5107(17) . ?

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
C00H S001 C00M 92.37(6) . . ?
C00M S002 C00Q 102.82(6) . . ?
C008 C003 C00C 122.42(11) . . ?
C008 C003 C004 119.65(11) . . ?
C00C C003 C004 117.93(11) . . ?
C005 C004 C00A 122.47(10) . . ?
C005 C004 C003 118.73(11) . . ?
C00A C004 C003 118.79(11) . . ?
C006 C005 C004 121.64(10) . . ?
C005 C006 C00D 122.12(11) . . ?
C005 C006 C007 119.23(11) . . ?
C00D C006 C007 118.64(11) . . ?
C008 C007 C00N 122.34(11) . . ?
C008 C007 C006 119.11(11) . . ?
C00N C007 C006 118.54(11) . . ?
C003 C008 C007 121.62(11) . . ?
C00A C009 C00E 118.48(11) . . ?
C00A C009 C00H 122.60(11) . . ?
C00E C009 C00H 118.92(11) . . ?
C009 C00A C004 121.87(11) . . ?
C00J C00B C00K 113.69(11) . . ?
C00E C00C C003 121.59(11) . . ?
C00F C00D C006 121.03(12) . . ?
C00C C00E C009 121.25(11) . . ?
C00D C00F C00L 120.30(12) . . ?
C00H C00G C00O 114.60(11) . . ?
C00G C00H C009 127.88(11) . . ?
C00G C00H S001 109.94(9) . . ?
C009 C00H S001 122.17(9) . . ?
C00K C00I C00Q 115.32(11) . . ?
C00B C00J C00P 113.20(11) . . ?
C00I C00K C00B 114.36(10) . . ?
C00N C00L C00F 120.82(12) . . ?
C00O C00M S001 111.43(9) . . ?
C00O C00M S002 129.79(10) . . ?
S001 C00M S002 118.76(7) . . ?
C00L C00N C007 120.66(12) . . ?
C00M C00O C00G 111.65(11) . . ?
C00M C00O C00P 125.80(12) . . ?
C00G C00O C00P 122.49(12) . . ?
C00O C00P C00J 112.02(10) . . ?
C00I C00Q S002 115.56(9) . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_rac-12
_database_code_depnum_ccdc_archive 'CCDC 2128003'
loop_
_audit_author_name
_audit_author_address
'Masahiro Hayakawa'
;Department of Chemistry, Graduate School of Science, Nagoya University
Japan
;
_audit_update_record             
;
2021-12-12 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            rac-oxTN-Pyrene
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 O S2'
_chemical_formula_weight         414.55

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'

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

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

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

_cell_length_a                   9.0966(2)
_cell_length_b                   10.4919(2)
_cell_length_c                   11.1191(2)
_cell_angle_alpha                91.4630(10)
_cell_angle_beta                 91.368(2)
_cell_angle_gamma                111.185(2)
_cell_volume                     988.55(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9429
_cell_measurement_theta_min      2.5520
_cell_measurement_theta_max      30.2720

_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.285
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11206
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.833
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3463
_reflns_number_gt                3143
_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       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+1.3672P] 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         3463
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.54638(7) 0.91602(6) 0.77022(6) 0.02595(18) Uani 1 1 d . . . . .
S2 S 0.81634(8) 0.97929(7) 0.60340(7) 0.0344(2) Uani 1 1 d . . . . .
O3 O 0.8827(2) 1.0984(2) 0.6857(2) 0.0513(6) Uani 1 1 d . . . . .
C4 C 0.3541(3) 0.8294(2) 0.7198(2) 0.0254(5) Uani 1 1 d . . . . .
C5 C 0.3490(3) 0.7968(3) 0.6001(2) 0.0275(5) Uani 1 1 d . . . . .
H5 H 0.253143 0.748158 0.556459 0.033 Uiso 1 1 calc R U . . .
C6 C 0.4970(3) 0.8409(2) 0.5456(2) 0.0274(5) Uani 1 1 d . . . . .
C7 C 0.6141(3) 0.9081(2) 0.6281(2) 0.0276(5) Uani 1 1 d . . . . .
C8 C 0.8726(3) 0.8465(3) 0.6688(2) 0.0350(6) Uani 1 1 d . . . . .
H8A H 0.983980 0.864175 0.650058 0.042 Uiso 1 1 calc R U . . .
H8AB H 0.867706 0.854660 0.757414 0.042 Uiso 1 1 calc R U . . .
C9 C 0.7748(3) 0.6996(3) 0.6286(3) 0.0361(6) Uani 1 1 d . . . . .
H9A H 0.797690 0.637547 0.685530 0.043 Uiso 1 1 calc R U . . .
H9AB H 0.661815 0.686228 0.634568 0.043 Uiso 1 1 calc R U . . .
C10 C 0.8013(4) 0.6575(3) 0.5031(3) 0.0407(7) Uani 1 1 d . . . . .
H10A H 0.748170 0.557006 0.493342 0.049 Uiso 1 1 calc R U . . .
H10B H 0.915769 0.678517 0.495444 0.049 Uiso 1 1 calc R U . . .
C11 C 0.7450(3) 0.7223(3) 0.4001(2) 0.0389(7) Uani 1 1 d . . . . .
H11A H 0.778484 0.692274 0.323766 0.047 Uiso 1 1 calc R U . . .
H11B H 0.798883 0.822787 0.408882 0.047 Uiso 1 1 calc R U . . .
C12 C 0.5649(3) 0.6896(3) 0.3896(2) 0.0353(6) Uani 1 1 d . . . . .
H12A H 0.526587 0.652533 0.307269 0.042 Uiso 1 1 calc R U . . .
H12B H 0.512156 0.617338 0.446465 0.042 Uiso 1 1 calc R U . . .
C13 C 0.5160(3) 0.8121(3) 0.4155(2) 0.0335(6) Uani 1 1 d . . . . .
H13A H 0.596069 0.894390 0.383042 0.040 Uiso 1 1 calc R U . . .
H13B H 0.414776 0.796588 0.371477 0.040 Uiso 1 1 calc R U . . .
C14 C 0.2284(3) 0.8083(2) 0.8053(2) 0.0236(5) Uani 1 1 d . . . . .
C15 C 0.2353(3) 0.9162(2) 0.8839(2) 0.0266(5) Uani 1 1 d . . . . .
H15 H 0.319238 1.001713 0.878075 0.032 Uiso 1 1 calc R U . . .
C16 C 0.1251(3) 0.9027(2) 0.9691(2) 0.0254(5) Uani 1 1 d . . . . .
H16 H 0.134968 0.978015 1.022141 0.030 Uiso 1 1 calc R U . . .
C17 C -0.0016(3) 0.7798(2) 0.9788(2) 0.0235(5) Uani 1 1 d . . . . .
C18 C -0.1202(3) 0.7630(2) 1.0652(2) 0.0260(5) Uani 1 1 d . . . . .
H18 H -0.113149 0.837680 1.118163 0.031 Uiso 1 1 calc R U . . .
C19 C -0.2409(3) 0.6445(3) 1.0730(2) 0.0284(6) Uani 1 1 d . . . . .
H19 H -0.319925 0.637412 1.129490 0.034 Uiso 1 1 calc R U . . .
C20 C -0.2536(3) 0.5280(3) 0.9980(2) 0.0262(5) Uani 1 1 d . . . . .
C21 C -0.3730(3) 0.4013(3) 1.0099(2) 0.0304(6) Uani 1 1 d . . . . .
H21 H -0.452121 0.391877 1.066921 0.036 Uiso 1 1 calc R U . . .
C22 C -0.3777(3) 0.2897(3) 0.9402(2) 0.0316(6) Uani 1 1 d . . . . .
H22 H -0.459606 0.203780 0.950071 0.038 Uiso 1 1 calc R U . . .
C23 C -0.2656(3) 0.3006(3) 0.8563(2) 0.0286(6) Uani 1 1 d . . . . .
H23 H -0.270136 0.222222 0.809445 0.034 Uiso 1 1 calc R U . . .
C24 C -0.1449(3) 0.4262(2) 0.8393(2) 0.0248(5) Uani 1 1 d . . . . .
C25 C -0.0262(3) 0.4413(2) 0.7547(2) 0.0265(5) Uani 1 1 d . . . . .
H25 H -0.030095 0.364584 0.705672 0.032 Uiso 1 1 calc R U . . .
C26 C 0.0922(3) 0.5622(2) 0.7422(2) 0.0254(5) Uani 1 1 d . . . . .
H26 H 0.169635 0.568782 0.684457 0.030 Uiso 1 1 calc R U . . .
C27 C 0.1041(3) 0.6810(2) 0.8140(2) 0.0226(5) Uani 1 1 d . . . . .
C28 C -0.0116(3) 0.6683(2) 0.9006(2) 0.0217(5) Uani 1 1 d . . . . .
C29 C -0.1376(3) 0.5411(2) 0.9124(2) 0.0229(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.721(3) . ?
S1 C4 1.726(2) . ?
S2 O3 1.461(2) . ?
S2 C7 1.749(3) . ?
S2 C8 1.812(3) . ?
C4 C5 1.361(4) . ?
C4 C14 1.463(4) . ?
C5 C6 1.413(4) . ?
C6 C7 1.360(4) . ?
C6 C13 1.497(4) . ?
C8 C9 1.524(4) . ?
C9 C10 1.504(4) . ?
C10 C11 1.517(4) . ?
C11 C12 1.549(4) . ?
C12 C13 1.527(4) . ?
C14 C15 1.394(3) . ?
C14 C27 1.411(3) . ?
C15 C16 1.369(4) . ?
C16 C17 1.393(3) . ?
C17 C28 1.414(3) . ?
C17 C18 1.428(4) . ?
C18 C19 1.335(4) . ?
C19 C20 1.430(4) . ?
C20 C21 1.391(4) . ?
C20 C29 1.409(4) . ?
C21 C22 1.376(4) . ?
C22 C23 1.375(4) . ?
C23 C24 1.398(3) . ?
C24 C29 1.417(3) . ?
C24 C25 1.418(4) . ?
C25 C26 1.348(3) . ?
C26 C27 1.431(3) . ?
C27 C28 1.417(3) . ?
C28 C29 1.422(3) . ?

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
C7 S1 C4 91.20(12) . . ?
O3 S2 C7 107.19(12) . . ?
O3 S2 C8 105.45(13) . . ?
C7 S2 C8 97.94(13) . . ?
C5 C4 C14 131.4(2) . . ?
C5 C4 S1 110.27(19) . . ?
C14 C4 S1 118.29(18) . . ?
C4 C5 C6 115.0(2) . . ?
C7 C6 C5 110.4(2) . . ?
C7 C6 C13 126.7(2) . . ?
C5 C6 C13 122.9(2) . . ?
C6 C7 S1 113.13(19) . . ?
C6 C7 S2 127.0(2) . . ?
S1 C7 S2 119.81(15) . . ?
C9 C8 S2 116.63(19) . . ?
C10 C9 C8 115.7(3) . . ?
C9 C10 C11 117.0(2) . . ?
C10 C11 C12 115.8(3) . . ?
C13 C12 C11 114.4(2) . . ?
C6 C13 C12 115.3(2) . . ?
C15 C14 C27 119.0(2) . . ?
C15 C14 C4 118.7(2) . . ?
C27 C14 C4 122.2(2) . . ?
C16 C15 C14 122.1(2) . . ?
C15 C16 C17 120.7(2) . . ?
C16 C17 C28 118.6(2) . . ?
C16 C17 C18 122.2(2) . . ?
C28 C17 C18 119.3(2) . . ?
C19 C18 C17 121.3(2) . . ?
C18 C19 C20 121.3(2) . . ?
C21 C20 C29 119.2(2) . . ?
C21 C20 C19 122.1(2) . . ?
C29 C20 C19 118.7(2) . . ?
C22 C21 C20 120.7(3) . . ?
C23 C22 C21 120.9(2) . . ?
C22 C23 C24 120.6(2) . . ?
C23 C24 C29 118.8(2) . . ?
C23 C24 C25 122.2(2) . . ?
C29 C24 C25 118.9(2) . . ?
C26 C25 C24 121.4(2) . . ?
C25 C26 C27 121.6(2) . . ?
C14 C27 C28 118.7(2) . . ?
C14 C27 C26 123.1(2) . . ?
C28 C27 C26 118.2(2) . . ?
C17 C28 C27 120.9(2) . . ?
C17 C28 C29 119.0(2) . . ?
C27 C28 C29 120.1(2) . . ?
C20 C29 C24 119.8(2) . . ?
C20 C29 C28 120.4(2) . . ?
C24 C29 C28 119.8(2) . . ?

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 S1 C4 C5 0.8(2) . . . . ?
C7 S1 C4 C14 -176.8(2) . . . . ?
C14 C4 C5 C6 176.6(2) . . . . ?
S1 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C4 C5 C6 C13 178.6(2) . . . . ?
C5 C6 C7 S1 0.8(3) . . . . ?
C13 C6 C7 S1 -177.9(2) . . . . ?
C5 C6 C7 S2 179.25(19) . . . . ?
C13 C6 C7 S2 0.5(4) . . . . ?
C4 S1 C7 C6 -0.9(2) . . . . ?
C4 S1 C7 S2 -179.52(16) . . . . ?
O3 S2 C7 C6 148.6(2) . . . . ?
C8 S2 C7 C6 -102.5(2) . . . . ?
O3 S2 C7 S1 -33.05(19) . . . . ?
C8 S2 C7 S1 75.90(17) . . . . ?
O3 S2 C8 C9 159.2(2) . . . . ?
C7 S2 C8 C9 48.8(2) . . . . ?
S2 C8 C9 C10 73.2(3) . . . . ?
C8 C9 C10 C11 -68.8(3) . . . . ?
C9 C10 C11 C12 -63.3(4) . . . . ?
C10 C11 C12 C13 112.5(3) . . . . ?
C7 C6 C13 C12 80.5(3) . . . . ?
C5 C6 C13 C12 -98.0(3) . . . . ?
C11 C12 C13 C6 -84.9(3) . . . . ?
C5 C4 C14 C15 -134.4(3) . . . . ?
S1 C4 C14 C15 42.6(3) . . . . ?
C5 C4 C14 C27 48.1(4) . . . . ?
S1 C4 C14 C27 -134.9(2) . . . . ?
C27 C14 C15 C16 -0.1(4) . . . . ?
C4 C14 C15 C16 -177.7(2) . . . . ?
C14 C15 C16 C17 -1.3(4) . . . . ?
C15 C16 C17 C28 1.5(4) . . . . ?
C15 C16 C17 C18 -178.9(2) . . . . ?
C16 C17 C18 C19 179.9(2) . . . . ?
C28 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 2.1(4) . . . . ?
C18 C19 C20 C21 175.9(2) . . . . ?
C18 C19 C20 C29 -1.6(4) . . . . ?
C29 C20 C21 C22 0.5(4) . . . . ?
C19 C20 C21 C22 -177.0(2) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C22 C23 C24 C29 1.8(3) . . . . ?
C22 C23 C24 C25 179.3(2) . . . . ?
C23 C24 C25 C26 -177.8(2) . . . . ?
C29 C24 C25 C26 -0.3(4) . . . . ?
C24 C25 C26 C27 0.2(4) . . . . ?
C15 C14 C27 C28 1.4(3) . . . . ?
C4 C14 C27 C28 178.9(2) . . . . ?
C15 C14 C27 C26 -176.2(2) . . . . ?
C4 C14 C27 C26 1.3(4) . . . . ?
C25 C26 C27 C14 178.4(2) . . . . ?
C25 C26 C27 C28 0.8(3) . . . . ?
C16 C17 C28 C27 -0.2(3) . . . . ?
C18 C17 C28 C27 -179.8(2) . . . . ?
C16 C17 C28 C29 178.0(2) . . . . ?
C18 C17 C28 C29 -1.7(3) . . . . ?
C14 C27 C28 C17 -1.3(3) . . . . ?
C26 C27 C28 C17 176.5(2) . . . . ?
C14 C27 C28 C29 -179.4(2) . . . . ?
C26 C27 C28 C29 -1.6(3) . . . . ?
C21 C20 C29 C24 0.6(3) . . . . ?
C19 C20 C29 C24 178.2(2) . . . . ?
C21 C20 C29 C28 -178.2(2) . . . . ?
C19 C20 C29 C28 -0.6(3) . . . . ?
C23 C24 C29 C20 -1.8(3) . . . . ?
C25 C24 C29 C20 -179.4(2) . . . . ?
C23 C24 C29 C28 177.0(2) . . . . ?
C25 C24 C29 C28 -0.5(3) . . . . ?
C17 C28 C29 C20 2.2(3) . . . . ?
C27 C28 C29 C20 -179.6(2) . . . . ?
C17 C28 C29 C24 -176.6(2) . . . . ?
C27 C28 C29 C24 1.5(3) . . . . ?

_refine_diff_density_max         1.041
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2128006'
loop_
_audit_author_name
_audit_author_address
'Masahiro Hayakawa'
;Department of Chemistry, Graduate School of Science, Nagoya University
Japan
;
_audit_update_record             
;
2021-12-12 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            TN-Napt
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 S2'
_chemical_formula_weight         324.48

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   11.3275(4)
_cell_length_b                   8.1766(3)
_cell_length_c                   34.8684(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3229.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7988
_cell_measurement_theta_min      2.1580
_cell_measurement_theta_max      27.1950

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.324
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.68346
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24371
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.336
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3683
_reflns_number_gt                2173
_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       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0272P)²+2.6134P] 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         3683
_refine_ls_number_parameters     236
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.1255
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.5607(2) 0.3949(3) 0.73990(8) 0.0272(7) Uani 1 1 d . . . . .
H1 H 0.490745 0.445774 0.730741 0.033 Uiso 1 1 calc R U . . .
C2 C 0.6410(2) 0.3368(3) 0.71402(9) 0.0264(6) Uani 1 1 d . . . . .
C3 C 0.7442(3) 0.2555(3) 0.72811(8) 0.0288(6) Uani 1 1 d . . . . .
H2 H 0.799875 0.211689 0.710525 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7631(2) 0.2404(3) 0.76641(9) 0.0310(7) Uani 1 1 d . . . . .
H3 H 0.831698 0.184919 0.775124 0.037 Uiso 1 1 calc R U . . .
C5 C 0.6833(2) 0.3050(3) 0.79361(8) 0.0266(7) Uani 1 1 d . . . . .
C6 C 0.7046(2) 0.2986(3) 0.83361(9) 0.0315(7) Uani 1 1 d . . . . .
H4 H 0.773927 0.246730 0.842987 0.038 Uiso 1 1 calc R U . . .
C7 C 0.6267(3) 0.3660(3) 0.85867(9) 0.0347(7) Uani 1 1 d . . . . .
H5 H 0.642484 0.362464 0.885419 0.042 Uiso 1 1 calc R U . . .
C8 C 0.5222(2) 0.4414(3) 0.84520(9) 0.0347(7) Uani 1 1 d . . . . .
H6 H 0.467993 0.487405 0.862954 0.042 Uiso 1 1 calc R U . . .
C9 C 0.4990(2) 0.4484(3) 0.80696(9) 0.0318(7) Uani 1 1 d . . . . .
H7 H 0.428390 0.498899 0.798285 0.038 Uiso 1 1 calc R U . . .
C10 C 0.5786(2) 0.3814(3) 0.77996(9) 0.0265(6) Uani 1 1 d . . . . .
S1 S 0.53068(10) 0.50606(13) 0.65547(3) 0.0278(3) Uani 0.876(2) 1 d . U P A 1
C11 C 0.6260(2) 0.3587(3) 0.67275(9) 0.0267(6) Uani 1 1 d D . . . .
C12 C 0.6786(8) 0.2809(13) 0.6430(4) 0.036(2) Uani 0.876(2) 1 d D U P A 1
H8 H 0.734615 0.195983 0.646784 0.043 Uiso 0.876(2) 1 calc R U P A 1
C13 C 0.6450(2) 0.3341(3) 0.60544(9) 0.0291(7) Uani 1 1 d D . . . .
C14 C 0.5638(2) 0.4576(3) 0.60872(8) 0.0297(7) Uani 1 1 d D . . . .
S2 S 0.49747(13) 0.5693(2) 0.57121(4) 0.0328(3) Uani 0.876(2) 1 d D U P A 1
C15 C 0.3569(2) 0.4631(4) 0.56637(10) 0.0470(9) Uani 1 1 d . . . . .
H9 H 0.346051 0.390687 0.588851 0.056 Uiso 0.876(2) 1 calc R U P A 1
H10 H 0.292548 0.544932 0.566716 0.056 Uiso 0.876(2) 1 calc R U P A 1
H11 H 0.329621 0.394014 0.587934 0.056 Uiso 0.124(2) 1 calc R U P A 2
H12 H 0.300066 0.554491 0.564073 0.056 Uiso 0.124(2) 1 calc R U P A 2
C16 C 0.3459(3) 0.3602(4) 0.52978(10) 0.0494(9) Uani 1 1 d . . . . .
H13 H 0.273417 0.293038 0.531630 0.059 Uiso 1 1 calc R U . . .
H14 H 0.336137 0.435055 0.507681 0.059 Uiso 1 1 calc R U . . .
C17 C 0.4491(3) 0.2483(4) 0.52182(9) 0.0457(9) Uani 1 1 d . . . . .
H15 H 0.518969 0.316671 0.515939 0.055 Uiso 1 1 calc R U . . .
H16 H 0.430995 0.183327 0.498602 0.055 Uiso 1 1 calc R U . . .
C18 C 0.4819(3) 0.1303(4) 0.55418(9) 0.0408(8) Uani 1 1 d . . . . .
H17 H 0.452328 0.174657 0.578788 0.049 Uiso 1 1 calc R U . . .
H18 H 0.442267 0.024120 0.549670 0.049 Uiso 1 1 calc R U . . .
C19 C 0.6141(3) 0.1020(4) 0.55741(10) 0.0407(8) Uani 1 1 d . . . . .
H19 H 0.643276 0.061072 0.532425 0.049 Uiso 0.876(2) 1 calc R U P A 1
H20 H 0.627905 0.014912 0.576623 0.049 Uiso 0.876(2) 1 calc R U P A 1
H21 H 0.641479 0.036422 0.535259 0.049 Uiso 0.124(2) 1 calc R U P A 2
H22 H 0.631227 0.039527 0.581089 0.049 Uiso 0.124(2) 1 calc R U P A 2
C20 C 0.6898(13) 0.2566(16) 0.5691(2) 0.046(2) Uani 0.876(2) 1 d D U P A 1
H23 H 0.773130 0.223314 0.572678 0.055 Uiso 0.876(2) 1 calc R U P A 1
H24 H 0.687146 0.337918 0.548053 0.055 Uiso 0.876(2) 1 calc R U P A 1
S3 S 0.7093(18) 0.252(3) 0.6407(7) 0.041(3) Uani 0.124(2) 1 d . U P A 2
S4 S 0.682(3) 0.267(3) 0.5584(4) 0.055(4) Uani 0.124(2) 1 d D U P A 2
C21 C 0.553(3) 0.458(4) 0.6523(9) 0.033(5) Uani 0.124(2) 1 d D U P A 2
H25 H 0.496911 0.525867 0.664893 0.039 Uiso 0.124(2) 1 calc R U P A 2
C22 C 0.490(4) 0.546(6) 0.5798(13) 0.042(6) Uani 0.124(2) 1 d D U P A 2
H26 H 0.537881 0.559751 0.556283 0.050 Uiso 0.124(2) 1 calc R U P A 2
H27 H 0.473957 0.657136 0.589930 0.050 Uiso 0.124(2) 1 calc R U P A 2


_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 1.366(4) . ?
C1 C10 1.416(4) . ?
C2 C3 1.432(4) . ?
C2 C11 1.460(4) . ?
C3 C4 1.358(4) . ?
C4 C5 1.413(4) . ?
C5 C6 1.416(4) . ?
C5 C10 1.423(4) . ?
C6 C7 1.359(4) . ?
C7 C8 1.415(4) . ?
C8 C9 1.360(4) . ?
C9 C10 1.413(4) . ?
S1 C14 1.719(3) . ?
S1 C11 1.726(3) . ?
C11 C12 1.356(10) . ?
C11 C21 1.360(14) . ?
C11 S3 1.70(2) . ?
C12 C13 1.430(12) . ?
C13 C14 1.370(4) . ?
C13 C20 1.506(8) . ?
C13 S3 1.58(2) . ?
C13 S4 1.779(10) . ?
C14 C22 1.500(13) . ?
C14 C21 1.53(3) . ?
C14 S2 1.763(3) . ?
S2 C15 1.821(3) . ?
C15 C16 1.533(4) . ?
C15 C22 1.72(5) . ?
C16 C17 1.511(4) . ?
C17 C18 1.531(4) . ?
C18 C19 1.519(4) . ?
C19 S4 1.55(3) . ?
C19 C20 1.581(14) . ?

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 C10 122.0(3) . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 C11 122.1(3) . . ?
C3 C2 C11 119.4(2) . . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 C5 121.7(3) . . ?
C4 C5 C6 122.6(3) . . ?
C4 C5 C10 118.2(3) . . ?
C6 C5 C10 119.2(3) . . ?
C7 C6 C5 120.5(3) . . ?
C6 C7 C8 120.4(3) . . ?
C9 C8 C7 120.4(3) . . ?
C8 C9 C10 120.9(3) . . ?
C9 C10 C1 122.4(2) . . ?
C9 C10 C5 118.6(3) . . ?
C1 C10 C5 118.9(3) . . ?
C14 S1 C11 91.94(14) . . ?
C12 C11 C2 130.3(5) . . ?
C21 C11 C2 131.3(16) . . ?
C21 C11 S3 107.3(17) . . ?
C2 C11 S3 121.4(8) . . ?
C12 C11 S1 109.6(5) . . ?
C2 C11 S1 120.2(2) . . ?
C11 C12 C13 116.2(6) . . ?
C14 C13 C12 109.1(4) . . ?
C14 C13 C20 127.4(5) . . ?
C12 C13 C20 123.5(6) . . ?
C14 C13 S3 123.9(8) . . ?
C14 C13 S4 117.5(9) . . ?
S3 C13 S4 118.6(11) . . ?
C13 C14 C22 132(2) . . ?
C13 C14 C21 98.0(7) . . ?
C22 C14 C21 129(2) . . ?
C13 C14 S1 113.3(2) . . ?
C13 C14 S2 127.3(2) . . ?
S1 C14 S2 119.41(17) . . ?
C14 S2 C15 101.19(15) . . ?
C16 C15 C22 121(2) . . ?
C16 C15 S2 114.2(2) . . ?
C17 C16 C15 115.0(3) . . ?
C16 C17 C18 115.8(3) . . ?
C19 C18 C17 112.9(3) . . ?
C18 C19 S4 110.8(10) . . ?
C18 C19 C20 115.6(5) . . ?
C13 C20 C19 111.7(8) . . ?
C13 S3 C11 92.2(8) . . ?
C19 S4 C13 100.0(13) . . ?
C11 C21 C14 118(2) . . ?
C14 C22 C15 119(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
C10 C1 C2 C3 2.1(4) . . . . ?
C10 C1 C2 C11 -176.5(2) . . . . ?
C1 C2 C3 C4 -1.7(4) . . . . ?
C11 C2 C3 C4 176.8(3) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 -176.4(3) . . . . ?
C3 C4 C5 C10 2.6(4) . . . . ?
C4 C5 C6 C7 178.4(3) . . . . ?
C10 C5 C6 C7 -0.7(4) . . . . ?
C5 C6 C7 C8 1.0(4) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C1 -176.2(3) . . . . ?
C8 C9 C10 C5 0.6(4) . . . . ?
C2 C1 C10 C9 176.7(2) . . . . ?
C2 C1 C10 C5 -0.1(4) . . . . ?
C4 C5 C10 C9 -179.2(2) . . . . ?
C6 C5 C10 C9 -0.1(4) . . . . ?
C4 C5 C10 C1 -2.3(4) . . . . ?
C6 C5 C10 C1 176.8(2) . . . . ?
C1 C2 C11 C12 -163.0(7) . . . . ?
C3 C2 C11 C12 18.5(8) . . . . ?
C1 C2 C11 C21 14(2) . . . . ?
C3 C2 C11 C21 -164(2) . . . . ?
C1 C2 C11 S3 -166.7(10) . . . . ?
C3 C2 C11 S3 14.8(11) . . . . ?
C1 C2 C11 S1 18.5(3) . . . . ?
C3 C2 C11 S1 -160.0(2) . . . . ?
C14 S1 C11 C12 0.4(6) . . . . ?
C14 S1 C11 C2 179.2(2) . . . . ?
C2 C11 C12 C13 -179.1(4) . . . . ?
S1 C11 C12 C13 -0.4(10) . . . . ?
C11 C12 C13 C14 0.2(10) . . . . ?
C11 C12 C13 C20 -177.0(9) . . . . ?
S3 C13 C14 C22 -177(3) . . . . ?
S4 C13 C14 C22 5(3) . . . . ?
S3 C13 C14 C21 -7.1(19) . . . . ?
S4 C13 C14 C21 174.4(19) . . . . ?
C12 C13 C14 S1 0.2(6) . . . . ?
C20 C13 C14 S1 177.2(7) . . . . ?
C12 C13 C14 S2 178.0(5) . . . . ?
C20 C13 C14 S2 -5.0(8) . . . . ?
C11 S1 C14 C13 -0.3(2) . . . . ?
C11 S1 C14 S2 -178.37(18) . . . . ?
C13 C14 S2 C15 98.2(3) . . . . ?
S1 C14 S2 C15 -84.1(2) . . . . ?
C14 S2 C15 C16 -108.8(2) . . . . ?
C22 C15 C16 C17 38.7(12) . . . . ?
S2 C15 C16 C17 48.9(3) . . . . ?
C15 C16 C17 C18 54.8(4) . . . . ?
C16 C17 C18 C19 -144.1(3) . . . . ?
C17 C18 C19 S4 50.2(6) . . . . ?
C17 C18 C19 C20 65.0(5) . . . . ?
C14 C13 C20 C19 -91.6(8) . . . . ?
C12 C13 C20 C19 85.0(10) . . . . ?
C18 C19 C20 C13 53.9(9) . . . . ?
C14 C13 S3 C11 6.0(16) . . . . ?
S4 C13 S3 C11 -175.5(13) . . . . ?
C21 C11 S3 C13 -2(2) . . . . ?
C2 C11 S3 C13 179.2(5) . . . . ?
C18 C19 S4 C13 72.9(13) . . . . ?
C14 C13 S4 C19 -105.3(12) . . . . ?
S3 C13 S4 C19 76.2(18) . . . . ?
C2 C11 C21 C14 177.0(11) . . . . ?
S3 C11 C21 C14 -2(3) . . . . ?
C13 C14 C21 C11 5(3) . . . . ?
C22 C14 C21 C11 176(3) . . . . ?
C13 C14 C22 C15 85(4) . . . . ?
C21 C14 C22 C15 -82(5) . . . . ?
C16 C15 C22 C14 -97(4) . . . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_18
_database_code_depnum_ccdc_archive 'CCDC 2133269'
loop_
_audit_author_name
_audit_author_address
'Masahiro Hayakawa'
;Department of Chemistry, Graduate School of Science, Nagoya University
Japan
;
_audit_update_record             
;
2022-01-08 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            dioxTN-Br
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 Br O2 S2'
_chemical_formula_weight         309.23

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.7355(3)
_cell_length_b                   9.6941(2)
_cell_length_c                   8.6079(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.813(4)
_cell_angle_gamma                90
_cell_volume                     585.90(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6897
_cell_measurement_theta_min      2.6020
_cell_measurement_theta_max      29.8430

_exptl_crystal_description       platlet
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_F_000             312
_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    3.841
_shelx_estimated_absorpt_T_min   0.514
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku Pilatus 200K
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7902
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.607
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2656
_reflns_number_gt                2532
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.990

_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       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²] 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_abs_structure_details 
;
 Flack x determined using 1138 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2656
_refine_ls_number_parameters     136
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0215
_refine_ls_wR_factor_ref         0.0531
_refine_ls_wR_factor_gt          0.0527
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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
Br01 Br 0.38153(5) 0.24817(3) -0.02032(4) 0.03896(12) Uani 1 1 d . . . . .
S002 S 0.93680(10) 0.61987(8) 0.48041(10) 0.02549(17) Uani 1 1 d . . . . .
S003 S 0.73106(11) 0.41768(8) 0.20806(10) 0.02559(17) Uani 1 1 d . . . . .
O004 O 0.8754(3) 0.7546(3) 0.5037(3) 0.0388(6) Uani 1 1 d . . . . .
O005 O 1.0466(3) 0.6069(3) 0.3816(3) 0.0386(6) Uani 1 1 d . . . . .
C006 C 0.5685(4) 0.5115(3) 0.3959(4) 0.0221(6) Uani 1 1 d . . . . .
C007 C 0.5030(4) 0.3686(3) 0.1633(4) 0.0254(6) Uani 1 1 d . . . . .
C008 C 0.4334(4) 0.4234(3) 0.2712(4) 0.0252(6) Uani 1 1 d . . . . .
H008 H 0.309700 0.405039 0.264254 0.030 Uiso 1 1 calc R U . . .
C009 C 0.5578(5) 0.4639(4) 0.6772(4) 0.0308(7) Uani 1 1 d . . . . .
H00A H 0.542211 0.509685 0.773380 0.037 Uiso 1 1 calc R U . . .
H00B H 0.452847 0.396355 0.626799 0.037 Uiso 1 1 calc R U . . .
C00A C 0.7459(4) 0.3848(4) 0.7498(4) 0.0314(7) Uani 1 1 d . . . . .
H00C H 0.776521 0.358187 0.653182 0.038 Uiso 1 1 calc R U . . .
H00D H 0.726478 0.298517 0.802018 0.038 Uiso 1 1 calc R U . . .
C00B C 0.5350(4) 0.5736(3) 0.5409(4) 0.0271(6) Uani 1 1 d . . . . .
H00E H 0.405010 0.612946 0.496456 0.033 Uiso 1 1 calc R U . . .
H00F H 0.627089 0.649300 0.593470 0.033 Uiso 1 1 calc R U . . .
C00C C 0.7340(4) 0.5184(3) 0.3744(4) 0.0207(6) Uani 1 1 d . . . . .
C00D C 1.0055(5) 0.5798(4) 0.8250(4) 0.0308(7) Uani 1 1 d . . . . .
H00G H 0.909853 0.654672 0.783397 0.037 Uiso 1 1 calc R U . . .
H00H H 1.115926 0.615416 0.925764 0.037 Uiso 1 1 calc R U . . .
C00E C 1.0712(4) 0.5463(3) 0.6845(4) 0.0238(6) Uani 1 1 d . . . . .
H00I H 1.069998 0.444857 0.671233 0.029 Uiso 1 1 calc R U . . .
H00J H 1.204947 0.577204 0.723896 0.029 Uiso 1 1 calc R U . . .
C00F C 0.9189(5) 0.4591(4) 0.8829(4) 0.0383(8) Uani 1 1 d . . . . .
H00K H 1.020411 0.389531 0.936714 0.046 Uiso 1 1 calc R U . . .
H00L H 0.882856 0.493737 0.973457 0.046 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C007 1.871(3) . ?
S002 O004 1.432(3) . ?
S002 O005 1.438(2) . ?
S002 C00C 1.749(3) . ?
S002 C00E 1.773(3) . ?
S003 C007 1.708(3) . ?
S003 C00C 1.726(3) . ?
C006 C00C 1.370(4) . ?
C006 C008 1.426(4) . ?
C006 C00B 1.503(4) . ?
C007 C008 1.361(5) . ?
C009 C00A 1.528(5) . ?
C009 C00B 1.538(5) . ?
C00A C00F 1.528(5) . ?
C00D C00E 1.530(4) . ?
C00D C00F 1.532(5) . ?

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
O004 S002 O005 118.39(16) . . ?
O004 S002 C00C 107.94(14) . . ?
O005 S002 C00C 105.40(15) . . ?
O004 S002 C00E 108.58(15) . . ?
O005 S002 C00E 107.76(14) . . ?
C00C S002 C00E 108.40(14) . . ?
C007 S003 C00C 89.85(14) . . ?
C00C C006 C008 111.1(3) . . ?
C00C C006 C00B 126.1(3) . . ?
C008 C006 C00B 122.5(3) . . ?
C008 C007 S003 113.9(2) . . ?
C008 C007 Br01 128.1(2) . . ?
S003 C007 Br01 118.00(17) . . ?
C007 C008 C006 111.8(3) . . ?
C00A C009 C00B 116.3(2) . . ?
C009 C00A C00F 117.0(3) . . ?
C006 C00B C009 110.6(3) . . ?
C006 C00C S003 113.4(2) . . ?
C006 C00C S002 129.9(2) . . ?
S003 C00C S002 116.60(17) . . ?
C00E C00D C00F 115.5(3) . . ?
C00D C00E S002 116.5(2) . . ?
C00A C00F C00D 118.7(3) . . ?

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_S-2
_database_code_depnum_ccdc_archive 'CCDC 2128005'
loop_
_audit_author_name
_audit_author_address
'Masahiro Hayakawa'
;Department of Chemistry, Graduate School of Science, Nagoya University
Japan
;
_audit_update_record             
;
2021-12-12 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'(S)-2-bromo-4,5,6,7,8,9-hexahydrothieno[2,3-b]thionine S-oxide'
_chemical_name_common            (S)-oxTN-Br
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 Br O S2'
_chemical_formula_weight         293.23

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.6628(2)
_cell_length_b                   9.6181(2)
_cell_length_c                   15.2176(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1121.56(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    12829
_cell_measurement_theta_min      2.4980
_cell_measurement_theta_max      30.8000

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    4.001
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku Saturn70 (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            15314
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.505
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2570
_reflns_number_gt                2485
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0153P)²+0.2873P] 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_abs_structure_details 
;
 Flack x determined using 1016 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2570
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0174
_refine_ls_wR_factor_ref         0.0384
_refine_ls_wR_factor_gt          0.0379
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.46066(4) 0.31253(3) 0.51591(2) 0.02091(7) Uani 1 1 d . . . . .
S002 S 0.77087(8) 0.57011(6) 0.19659(4) 0.01464(13) Uani 1 1 d . . . . .
S003 S 0.70470(9) 0.45255(7) 0.37849(4) 0.01657(14) Uani 1 1 d . . . . .
O004 O 0.9165(2) 0.64603(19) 0.24162(13) 0.0239(4) Uani 1 1 d . . . . .
C005 C 0.4509(3) 0.4853(2) 0.26685(16) 0.0136(5) Uani 1 1 d . . . . .
C006 C 0.5042(3) 0.4079(3) 0.05210(16) 0.0163(5) Uani 1 1 d . . . . .
H00A H 0.461132 0.405752 -0.007822 0.020 Uiso 1 1 calc R U . . .
H00B H 0.565772 0.495156 0.059828 0.020 Uiso 1 1 calc R U . . .
C007 C 0.7343(3) 0.2828(2) 0.15018(17) 0.0167(5) Uani 1 1 d . . . . .
H00C H 0.649601 0.281090 0.197531 0.020 Uiso 1 1 calc R U . . .
H00D H 0.797945 0.195701 0.152150 0.020 Uiso 1 1 calc R U . . .
C008 C 0.3458(3) 0.5204(3) 0.18624(16) 0.0161(5) Uani 1 1 d . . . . .
H00E H 0.391099 0.605780 0.161168 0.019 Uiso 1 1 calc R U . . .
H00F H 0.226129 0.537672 0.203867 0.019 Uiso 1 1 calc R U . . .
C009 C 0.6354(4) 0.2896(3) 0.06312(17) 0.0191(6) Uani 1 1 d . . . . .
H00G H 0.720347 0.296417 0.016064 0.023 Uiso 1 1 calc R U . . .
H00H H 0.573645 0.202370 0.055423 0.023 Uiso 1 1 calc R U . . .
C00A C 0.6260(3) 0.5103(3) 0.27814(16) 0.0136(5) Uani 1 1 d . . . . .
C00B C 0.3461(3) 0.4072(3) 0.11445(17) 0.0168(5) Uani 1 1 d . . . . .
H00I H 0.340426 0.317072 0.142904 0.020 Uiso 1 1 calc R U . . .
H00J H 0.241106 0.417592 0.079490 0.020 Uiso 1 1 calc R U . . .
C00C C 0.3790(3) 0.4173(3) 0.34188(17) 0.0157(5) Uani 1 1 d . . . . .
H00K H 0.262160 0.392249 0.346879 0.019 Uiso 1 1 calc R U . . .
C00D C 0.4999(3) 0.3934(2) 0.40504(16) 0.0161(6) Uani 1 1 d . . . . .
C00E C 0.8627(3) 0.4008(3) 0.16790(18) 0.0171(5) Uani 1 1 d . . . . .
H00L H 0.934568 0.412634 0.115963 0.021 Uiso 1 1 calc R U . . .
H00M H 0.939200 0.372072 0.215325 0.021 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C00D 1.882(3) . ?
S002 O004 1.4992(18) . ?
S002 C00A 1.761(3) . ?
S002 C00E 1.827(3) . ?
S003 C00D 1.717(3) . ?
S003 C00A 1.733(3) . ?
C005 C00A 1.374(3) . ?
C005 C00C 1.427(3) . ?
C005 C008 1.506(3) . ?
C006 C009 1.527(4) . ?
C006 C00B 1.539(3) . ?
C007 C00E 1.526(4) . ?
C007 C009 1.528(4) . ?
C008 C00B 1.542(3) . ?
C00C C00D 1.355(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
O004 S002 C00A 107.82(11) . . ?
O004 S002 C00E 104.88(11) . . ?
C00A S002 C00E 96.90(12) . . ?
C00D S003 C00A 89.76(12) . . ?
C00A C005 C00C 111.0(2) . . ?
C00A C005 C008 125.8(2) . . ?
C00C C005 C008 123.2(2) . . ?
C009 C006 C00B 116.6(2) . . ?
C00E C007 C009 116.2(2) . . ?
C005 C008 C00B 114.7(2) . . ?
C006 C009 C007 117.0(2) . . ?
C005 C00A S003 113.2(2) . . ?
C005 C00A S002 125.8(2) . . ?
S003 C00A S002 120.41(15) . . ?
C006 C00B C008 115.8(2) . . ?
C00D C00C C005 112.4(2) . . ?
C00C C00D S003 113.69(19) . . ?
C00C C00D Br01 126.65(19) . . ?
S003 C00D Br01 119.60(14) . . ?
C007 C00E S002 117.18(18) . . ?

_refine_diff_density_max         0.265
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 2128000'
loop_
_audit_author_name
_audit_author_address
'Masahiro Hayakawa'
;Department of Chemistry, Graduate School of Science, Nagoya University
Japan
;
_audit_update_record             
;
2021-12-12 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            TN-Pyrene
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 S2'
_chemical_formula_weight         398.55

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

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

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

_cell_length_a                   7.59897(14)
_cell_length_b                   9.8836(2)
_cell_length_c                   14.0367(3)
_cell_angle_alpha                90.1743(18)
_cell_angle_beta                 96.6412(16)
_cell_angle_gamma                110.7438(19)
_cell_volume                     978.17(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    146(2)
_cell_measurement_reflns_used    12178
_cell_measurement_theta_min      2.2560
_cell_measurement_theta_max      30.9310

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.281
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93322
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      146(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn70 (4x4 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12135
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.071
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             4315
_reflns_number_gt                4099
_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       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+0.2914P] 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         4315
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0880
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.44794(4) 0.74824(3) 0.15214(2) 0.02439(9) Uani 1 1 d . . . . .
C1 C 0.19479(17) 0.90611(12) -0.06591(8) 0.0280(2) Uani 1 1 d . . . . .
H1A H 0.279772 0.910851 -0.115199 0.034 Uiso 1 1 calc R U . . .
H1AB H 0.191870 1.004409 -0.055692 0.034 Uiso 1 1 calc R U . . .
C2 C 0.31263(15) 0.83866(11) 0.19347(8) 0.0233(2) Uani 1 1 d . . . . .
S3 S 0.48609(4) 0.71903(3) -0.05689(2) 0.03079(10) Uani 1 1 d . . . . .
C4 C -0.01938(17) 0.64695(14) -0.11957(9) 0.0328(3) Uani 1 1 d . . . . .
H4A H -0.154211 0.585515 -0.137388 0.039 Uiso 1 1 calc R U . . .
H4AB H 0.026122 0.612602 -0.058759 0.039 Uiso 1 1 calc R U . . .
C5 C 0.27367(15) 0.86040(11) 0.02635(8) 0.0239(2) Uani 1 1 d . . . . .
C6 C 0.30496(14) 0.97862(11) 0.34180(8) 0.0208(2) Uani 1 1 d . . . . .
C7 C 0.35347(16) 1.23529(12) 0.33927(8) 0.0252(2) Uani 1 1 d . . . . .
H7 H 0.385265 1.322642 0.306003 0.030 Uiso 1 1 calc R U . . .
C8 C 0.19274(17) 0.97341(14) 0.63162(8) 0.0292(2) Uani 1 1 d . . . . .
H8 H 0.166026 0.971298 0.696182 0.035 Uiso 1 1 calc R U . . .
C9 C 0.22329(17) 1.23124(14) 0.62455(9) 0.0302(2) Uani 1 1 d . . . . .
H9 H 0.195607 1.231204 0.688843 0.036 Uiso 1 1 calc R U . . .
C10 C 0.19624(16) 0.85299(13) 0.58850(8) 0.0280(2) Uani 1 1 d . . . . .
H10 H 0.172827 0.767529 0.623482 0.034 Uiso 1 1 calc R U . . .
C11 C 0.25796(18) 1.35616(14) 0.57405(9) 0.0323(3) Uani 1 1 d . . . . .
H11 H 0.253139 1.440902 0.603984 0.039 Uiso 1 1 calc R U . . .
C12 C 0.23461(16) 0.72518(12) 0.44485(8) 0.0263(2) Uani 1 1 d . . . . .
H12 H 0.214648 0.639555 0.479365 0.032 Uiso 1 1 calc R U . . .
C13 C 0.29955(17) 1.35922(12) 0.48053(9) 0.0285(2) Uani 1 1 d . . . . .
H13 H 0.323027 1.445890 0.446878 0.034 Uiso 1 1 calc R U . . .
C14 C 0.30727(15) 1.23577(11) 0.43523(8) 0.0231(2) Uani 1 1 d . . . . .
C15 C 0.23439(15) 0.85031(12) 0.49112(8) 0.0228(2) Uani 1 1 d . . . . .
C16 C 0.22866(15) 1.10499(13) 0.58175(8) 0.0248(2) Uani 1 1 d . . . . .
C17 C 0.26993(14) 1.10670(11) 0.48563(7) 0.0212(2) Uani 1 1 d . . . . .
C18 C 0.35301(16) 1.11379(12) 0.29483(8) 0.0240(2) Uani 1 1 d . . . . .
H18 H 0.385088 1.117669 0.231199 0.029 Uiso 1 1 calc R U . . .
C19 C 0.1859(2) 0.51406(15) -0.17989(10) 0.0432(3) Uani 1 1 d . . . . .
H19A H 0.260402 0.513372 -0.233141 0.052 Uiso 1 1 calc R U . . .
H19B H 0.083785 0.417815 -0.181546 0.052 Uiso 1 1 calc R U . . .
C20 C 0.27051(14) 0.97831(11) 0.43923(7) 0.0202(2) Uani 1 1 d . . . . .
C21 C -0.00572(17) 0.80215(14) -0.10298(9) 0.0328(3) Uani 1 1 d . . . . .
H21A H -0.092465 0.804414 -0.056031 0.039 Uiso 1 1 calc R U . . .
H21B H -0.049255 0.836942 -0.164090 0.039 Uiso 1 1 calc R U . . .
C22 C 0.22989(16) 0.89123(12) 0.11779(8) 0.0261(2) Uani 1 1 d . . . . .
H22 H 0.149456 0.944207 0.125779 0.031 Uiso 1 1 calc R U . . .
C23 C 0.29484(15) 0.84814(11) 0.29621(8) 0.0222(2) Uani 1 1 d . . . . .
C24 C 0.3154(2) 0.53508(14) -0.08524(9) 0.0371(3) Uani 1 1 d . . . . .
H24A H 0.386414 0.468416 -0.086816 0.044 Uiso 1 1 calc R U . . .
H24B H 0.235293 0.506617 -0.032583 0.044 Uiso 1 1 calc R U . . .
C25 C 0.26339(16) 0.72424(12) 0.34982(8) 0.0256(2) Uani 1 1 d . . . . .
H25 H 0.261894 0.637440 0.319875 0.031 Uiso 1 1 calc R U . . .
C26 C 0.0950(2) 0.62768(14) -0.19801(9) 0.0350(3) Uani 1 1 d . . . . .
H26A H 0.010179 0.601210 -0.259531 0.042 Uiso 1 1 calc R U . . .
H26B H 0.196171 0.721867 -0.205339 0.042 Uiso 1 1 calc R U . . .
C27 C 0.38995(15) 0.78104(12) 0.03358(8) 0.0237(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.7258(11) . ?
S1 C27 1.7332(11) . ?
C1 C5 1.5020(15) . ?
C1 C21 1.5338(16) . ?
C2 C22 1.3690(16) . ?
C2 C23 1.4697(15) . ?
S3 C27 1.7462(11) . ?
S3 C24 1.8307(14) . ?
C4 C21 1.5158(19) . ?
C4 C26 1.5300(18) . ?
C5 C27 1.3700(15) . ?
C5 C22 1.4209(15) . ?
C6 C23 1.4114(14) . ?
C6 C20 1.4217(15) . ?
C6 C18 1.4382(14) . ?
C7 C18 1.3503(15) . ?
C7 C14 1.4311(15) . ?
C8 C10 1.3436(18) . ?
C8 C16 1.4332(17) . ?
C9 C11 1.3836(19) . ?
C9 C16 1.3988(16) . ?
C10 C15 1.4318(16) . ?
C11 C13 1.3833(18) . ?
C12 C25 1.3769(16) . ?
C12 C15 1.3958(16) . ?
C13 C14 1.3968(15) . ?
C14 C17 1.4157(15) . ?
C15 C20 1.4185(15) . ?
C16 C17 1.4189(15) . ?
C17 C20 1.4262(15) . ?
C19 C26 1.521(2) . ?
C19 C24 1.526(2) . ?
C23 C25 1.4011(15) . ?

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 S1 C27 92.48(5) . . ?
C5 C1 C21 112.49(9) . . ?
C22 C2 C23 129.01(10) . . ?
C22 C2 S1 109.81(8) . . ?
C23 C2 S1 121.17(8) . . ?
C27 S3 C24 102.58(6) . . ?
C21 C4 C26 113.60(10) . . ?
C27 C5 C22 111.54(10) . . ?
C27 C5 C1 125.23(10) . . ?
C22 C5 C1 123.19(10) . . ?
C23 C6 C20 119.00(9) . . ?
C23 C6 C18 122.97(10) . . ?
C20 C6 C18 118.02(9) . . ?
C18 C7 C14 121.65(10) . . ?
C10 C8 C16 121.04(11) . . ?
C11 C9 C16 120.57(11) . . ?
C8 C10 C15 121.62(11) . . ?
C13 C11 C9 120.83(11) . . ?
C25 C12 C15 120.85(10) . . ?
C11 C13 C14 120.47(11) . . ?
C13 C14 C17 119.32(10) . . ?
C13 C14 C7 122.19(10) . . ?
C17 C14 C7 118.50(10) . . ?
C12 C15 C20 118.71(10) . . ?
C12 C15 C10 122.20(10) . . ?
C20 C15 C10 119.09(10) . . ?
C9 C16 C17 119.05(11) . . ?
C9 C16 C8 122.16(11) . . ?
C17 C16 C8 118.79(10) . . ?
C14 C17 C16 119.76(10) . . ?
C14 C17 C20 120.00(10) . . ?
C16 C17 C20 120.23(10) . . ?
C7 C18 C6 121.38(10) . . ?
C26 C19 C24 115.37(11) . . ?
C15 C20 C6 120.55(10) . . ?
C15 C20 C17 119.22(10) . . ?
C6 C20 C17 120.23(10) . . ?
C4 C21 C1 113.83(10) . . ?
C2 C22 C5 114.79(10) . . ?
C25 C23 C6 119.15(10) . . ?
C25 C23 C2 119.34(10) . . ?
C6 C23 C2 121.50(9) . . ?
C19 C24 S3 115.47(10) . . ?
C12 C25 C23 121.62(10) . . ?
C19 C26 C4 115.04(11) . . ?
C5 C27 S1 111.37(8) . . ?
C5 C27 S3 129.15(9) . . ?
S1 C27 S3 119.43(6) . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_S-13_323K
_database_code_depnum_ccdc_archive 'CCDC 2128004'
loop_
_audit_author_name
_audit_author_address
'Masahiro Hayakawa'
;Department of Chemistry, Graduate School of Science, Nagoya University
Japan
;
_audit_update_record             
;
2021-12-12 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C62 H96 O4 S2'
_chemical_formula_weight         969.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.3391(4)
_cell_length_b                   10.2673(4)
_cell_length_c                   34.7678(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.371(4)
_cell_angle_gamma                90
_cell_volume                     2958.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    323(2)
_cell_measurement_reflns_used    7758
_cell_measurement_theta_min      2.2470
_cell_measurement_theta_max      27.6280

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.088
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.31152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      323(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16539
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.069
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.761
_diffrn_reflns_point_group_measured_fraction_full 0.781
_reflns_number_total             9923
_reflns_number_gt                7677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.493
_reflns_Friedel_fraction_max     0.533
_reflns_Friedel_fraction_full    0.570

_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       ?
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1064P)²] 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_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.06(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9923
_refine_ls_number_parameters     616
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1426
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
S001 S 1.36141(9) -0.08568(8) 0.02716(2) 0.0539(2) Uani 1 1 d . . . . .
S002 S 1.53151(10) -0.25051(8) -0.02659(2) 0.0595(2) Uani 1 1 d . . . . .
O003 O 1.3646(3) -0.2717(3) -0.04467(8) 0.0866(9) Uani 1 1 d . . . . .
C004 C 1.2102(4) 0.2197(3) 0.14260(9) 0.0555(8) Uani 1 1 d . . . . .
C005 C 0.9658(4) 0.3305(4) 0.15706(9) 0.0591(8) Uani 1 1 d . . . . .
O006 O 0.6431(5) 0.6895(4) 0.24527(10) 0.1038(11) Uani 1 1 d . . . . .
C007 C 1.4489(3) -0.0472(3) 0.07323(9) 0.0499(7) Uani 1 1 d . . . . .
C008 C 0.8794(4) 0.4210(4) 0.18088(10) 0.0646(8) Uani 1 1 d . . . . .
C20 C 1.1288(4) 0.3060(4) 0.16499(10) 0.0629(9) Uani 1 1 d . . . . .
H1 H 1.186501 0.348066 0.185817 0.076 Uiso 1 1 calc R U . . .
C21 C 1.5916(4) -0.1125(4) 0.08089(9) 0.0582(8) Uani 1 1 d . . . . .
H2 H 1.657187 -0.103249 0.104166 0.070 Uiso 1 1 calc R U . . .
C00B C 1.1234(4) 0.1535(3) 0.11102(9) 0.0523(7) Uani 1 1 d . . . . .
C00C C 1.6323(3) -0.1945(3) 0.05111(9) 0.0540(7) Uani 1 1 d . . . . .
C00D C 1.5195(4) -0.1869(3) 0.01963(10) 0.0528(7) Uani 1 1 d . . . . .
O00E O 0.5223(5) 0.6346(5) 0.17258(11) 0.1227(15) Uani 1 1 d . . . . .
C00F C 1.3668(4) 0.0416(3) 0.09675(9) 0.0512(7) Uani 1 1 d . . . . .
C00G C 1.3789(4) 0.1936(4) 0.14998(10) 0.0630(9) Uani 1 1 d . . . . .
H3 H 1.439434 0.236926 0.170114 0.076 Uiso 1 1 calc R U . . .
C00H C 1.2039(4) 0.0679(3) 0.08898(9) 0.0530(7) Uani 1 1 d . . . . .
H4 H 1.145837 0.026429 0.068098 0.064 Uiso 1 1 calc R U . . .
C00I C 1.4525(4) 0.1078(4) 0.12853(10) 0.0620(9) Uani 1 1 d . . . . .
H5 H 1.562006 0.091437 0.134661 0.074 Uiso 1 1 calc R U . . .
O10 O 0.8995(4) 0.5623(4) 0.27824(9) 0.1098(13) Uani 1 1 d . . . . .
C00K C 0.8821(4) 0.2634(4) 0.12479(10) 0.0605(8) Uani 1 1 d . . . . .
H6 H 0.772094 0.277980 0.118710 0.073 Uiso 1 1 calc R U . . .
C00L C 0.9340(5) 0.4462(4) 0.21840(11) 0.0738(10) Uani 1 1 d . . . . .
H7 H 1.027361 0.405306 0.229513 0.089 Uiso 1 1 calc R U . . .
C00M C 1.7851(4) -0.2747(4) 0.05315(11) 0.0679(9) Uani 1 1 d . . . . .
H8 H 1.762067 -0.354248 0.038535 0.082 Uiso 1 1 calc R U . . .
H9 H 1.815861 -0.299078 0.079910 0.082 Uiso 1 1 calc R U . . .
C00N C 1.9278(4) -0.2073(5) 0.03791(13) 0.0773(11) Uani 1 1 d . . . . .
H10 H 2.026118 -0.246571 0.050228 0.093 Uiso 1 1 calc R U . . .
H11 H 1.927923 -0.116732 0.045901 0.093 Uiso 1 1 calc R U . . .
C00O C 0.9567(4) 0.1805(4) 0.10310(10) 0.0607(8) Uani 1 1 d . . . . .
H96 H 0.897635 0.139622 0.082267 0.073 Uiso 1 1 calc R U . . .
C00P C 0.6577(5) 0.5672(5) 0.18658(13) 0.0861(13) Uani 1 1 d . . . . .
C00Q C 0.7377(5) 0.4834(4) 0.16424(11) 0.0763(11) Uani 1 1 d . . . . .
H12 H 0.698667 0.468160 0.138527 0.092 Uiso 1 1 calc R U . . .
C00R C 0.7138(6) 0.5933(5) 0.22428(13) 0.0889(14) Uani 1 1 d . . . . .
C00S C 1.7345(5) -0.0256(4) -0.02712(14) 0.0814(11) Uani 1 1 d . . . . .
H13 H 1.735232 0.060982 -0.038254 0.098 Uiso 1 1 calc R U . . .
H14 H 1.713306 -0.015847 -0.000394 0.098 Uiso 1 1 calc R U . . .
C00T C 1.9330(4) -0.2114(4) -0.00609(13) 0.0784(11) Uani 1 1 d . . . . .
H15 H 2.038548 -0.242531 -0.011068 0.094 Uiso 1 1 calc R U . . .
H16 H 1.854174 -0.274565 -0.016955 0.094 Uiso 1 1 calc R U . . .
C00U C 0.8536(5) 0.5315(5) 0.24052(12) 0.0846(12) Uani 1 1 d . . . . .
C00V C 1.9008(5) -0.0834(5) -0.02738(15) 0.0925(13) Uani 1 1 d . . . . .
H17 H 1.978898 -0.020115 -0.016232 0.111 Uiso 1 1 calc R U . . .
H18 H 1.920274 -0.096249 -0.054109 0.111 Uiso 1 1 calc R U . . .
C00W C 0.4483(6) 0.6118(6) 0.13701(13) 0.0904(13) Uani 1 1 d . . . . .
H19 H 0.418666 0.520593 0.134435 0.108 Uiso 1 1 calc R U . . .
H20 H 0.520499 0.632011 0.117802 0.108 Uiso 1 1 calc R U . . .
C00X C 1.1922(6) 0.4837(6) 0.36369(14) 0.0987(15) Uani 1 1 d . . . . .
H21 H 1.291241 0.497229 0.351998 0.118 Uiso 1 1 calc R U . . .
H22 H 1.172560 0.390704 0.364417 0.118 Uiso 1 1 calc R U . . .
C00Y C 1.5080(7) 0.4693(7) 0.49719(16) 0.1086(17) Uani 1 1 d . . . . .
H23 H 1.484576 0.377242 0.499459 0.130 Uiso 1 1 calc R U . . .
H24 H 1.607278 0.476760 0.485229 0.130 Uiso 1 1 calc R U . . .
C00Z C 0.2996(7) 0.6955(7) 0.13064(17) 0.1114(19) Uani 1 1 d . . . . .
H25 H 0.333001 0.785886 0.133324 0.134 Uiso 1 1 calc R U . . .
H26 H 0.252164 0.683438 0.104124 0.134 Uiso 1 1 calc R U . . .
C010 C 1.3499(7) 0.4731(6) 0.43047(14) 0.1010(16) Uani 1 1 d . . . . .
H27 H 1.449092 0.482533 0.418577 0.121 Uiso 1 1 calc R U . . .
H28 H 1.327940 0.380713 0.432473 0.121 Uiso 1 1 calc R U . . .
C011 C 1.5952(5) -0.1012(4) -0.04851(11) 0.0754(10) Uani 1 1 d . . . . .
H29 H 1.624608 -0.122691 -0.073978 0.091 Uiso 1 1 calc R U . . .
H30 H 1.502724 -0.043475 -0.052230 0.091 Uiso 1 1 calc R U . . .
C012 C 1.3737(6) 0.5311(7) 0.47078(14) 0.1005(15) Uani 1 1 d . . . . .
H31 H 1.396177 0.623390 0.468677 0.121 Uiso 1 1 calc R U . . .
H32 H 1.273869 0.522502 0.482463 0.121 Uiso 1 1 calc R U . . .
C013 C 1.0543(6) 0.5482(6) 0.33878(13) 0.1011(16) Uani 1 1 d . . . . .
H33 H 0.954801 0.533597 0.350176 0.121 Uiso 1 1 calc R U . . .
H34 H 1.073020 0.641435 0.338263 0.121 Uiso 1 1 calc R U . . .
C014 C 1.0361(6) 0.4968(6) 0.29805(13) 0.0939(15) Uani 1 1 d . . . . .
H35 H 1.132326 0.514789 0.285644 0.113 Uiso 1 1 calc R U . . .
H36 H 1.018390 0.403408 0.297956 0.113 Uiso 1 1 calc R U . . .
C015 C 1.6703(7) 0.4651(7) 0.56305(17) 0.1145(18) Uani 1 1 d . . . . .
H37 H 1.646095 0.373448 0.565871 0.137 Uiso 1 1 calc R U . . .
H38 H 1.768267 0.470973 0.550484 0.137 Uiso 1 1 calc R U . . .
C016 C 1.7019(8) 0.5242(8) 0.60259(16) 0.124(2) Uani 1 1 d . . . . .
H39 H 1.604104 0.520778 0.615297 0.149 Uiso 1 1 calc R U . . .
H40 H 1.731723 0.614919 0.600254 0.149 Uiso 1 1 calc R U . . .
C017 C 1.2139(6) 0.5358(6) 0.40468(13) 0.0973(14) Uani 1 1 d . . . . .
H41 H 1.233552 0.628775 0.403780 0.117 Uiso 1 1 calc R U . . .
H42 H 1.114155 0.522948 0.416124 0.117 Uiso 1 1 calc R U . . .
C018 C 1.5350(7) 0.5265(7) 0.53707(14) 0.1034(15) Uani 1 1 d . . . . .
H43 H 1.436178 0.518160 0.549183 0.124 Uiso 1 1 calc R U . . .
H44 H 1.557407 0.618762 0.534832 0.124 Uiso 1 1 calc R U . . .
C019 C 0.5182(7) 0.6414(8) 0.2639(2) 0.123(2) Uani 1 1 d . . . . .
H45 H 0.556684 0.570619 0.281000 0.147 Uiso 1 1 calc R U . . .
H46 H 0.433549 0.608009 0.245129 0.147 Uiso 1 1 calc R U . . .
C01A C 0.8784(10) 0.7829(8) 0.4527(2) 0.136(2) Uani 1 1 d . . . . .
H47 H 0.978463 0.794420 0.441271 0.164 Uiso 1 1 calc R U . . .
H48 H 0.838671 0.869397 0.457592 0.164 Uiso 1 1 calc R U . . .
C01B C 1.2066(14) 0.7876(11) 0.5837(3) 0.173(4) Uani 1 1 d . . . . .
H49 H 1.303126 0.797290 0.570801 0.208 Uiso 1 1 calc R U . . .
H50 H 1.168537 0.875107 0.588089 0.208 Uiso 1 1 calc R U . . .
C01C C 1.0396(10) 0.7832(8) 0.5189(2) 0.140(2) Uani 1 1 d . . . . .
H51 H 1.137865 0.793749 0.506680 0.168 Uiso 1 1 calc R U . . .
H52 H 1.000652 0.870202 0.523515 0.168 Uiso 1 1 calc R U . . .
C01D C 0.7620(8) 0.7242(8) 0.4226(2) 0.126(2) Uani 1 1 d . . . . .
H53 H 0.801381 0.637790 0.417416 0.151 Uiso 1 1 calc R U . . .
H54 H 0.661430 0.712833 0.433759 0.151 Uiso 1 1 calc R U . . .
C01E C 1.0850(10) 0.7285(9) 0.5552(3) 0.152(3) Uani 1 1 d . . . . .
H55 H 1.121896 0.640775 0.550657 0.183 Uiso 1 1 calc R U . . .
H56 H 0.987248 0.719771 0.567719 0.183 Uiso 1 1 calc R U . . .
C01F C 0.9193(8) 0.7229(8) 0.4896(3) 0.135(2) Uani 1 1 d . . . . .
H57 H 0.957276 0.635685 0.484788 0.162 Uiso 1 1 calc R U . . .
H58 H 0.820016 0.713312 0.501398 0.162 Uiso 1 1 calc R U . . .
C01G C 0.7237(10) 0.7869(8) 0.3859(2) 0.135(2) Uani 1 1 d . . . . .
H59 H 0.824889 0.800010 0.375175 0.162 Uiso 1 1 calc R U . . .
H60 H 0.682771 0.872699 0.391231 0.162 Uiso 1 1 calc R U . . .
C01H C 0.0473(9) 0.7708(10) 0.1550(3) 0.151(3) Uani 1 1 d . . . . .
H61 H 0.046110 0.827710 0.132691 0.181 Uiso 1 1 calc R U . . .
H62 H -0.054152 0.723679 0.152685 0.181 Uiso 1 1 calc R U . . .
C01I C 0.0576(13) 0.8483(13) 0.1889(3) 0.188(4) Uani 1 1 d . . . . .
H63 H 0.150985 0.904811 0.189354 0.226 Uiso 1 1 calc R U . . .
H64 H 0.073537 0.791858 0.211349 0.226 Uiso 1 1 calc R U . . .
C01J C 0.4527(8) 0.7496(8) 0.2871(2) 0.130(2) Uani 1 1 d . . . . .
H65 H 0.415898 0.819589 0.269543 0.156 Uiso 1 1 calc R U . . .
H66 H 0.359629 0.717023 0.298521 0.156 Uiso 1 1 calc R U . . .
C01K C -0.3842(17) 1.2316(18) 0.2643(4) 0.219(6) Uani 1 1 d . . . . .
H67 H -0.359020 1.299381 0.283440 0.262 Uiso 1 1 calc R U . . .
H68 H -0.395707 1.274101 0.239206 0.262 Uiso 1 1 calc R U . . .
C01L C 0.6105(8) 0.7302(8) 0.3550(2) 0.123(2) Uani 1 1 d . . . . .
H69 H 0.510156 0.712833 0.365720 0.148 Uiso 1 1 calc R U . . .
H70 H 0.653901 0.646673 0.348177 0.148 Uiso 1 1 calc R U . . .
C01M C 1.8383(10) 0.4513(11) 0.6274(2) 0.172(4) Uani 1 1 d . . . . .
H71 H 1.808331 0.360325 0.629018 0.206 Uiso 1 1 calc R U . . .
H72 H 1.935374 0.455445 0.614464 0.206 Uiso 1 1 calc R U . . .
C01N C -0.5297(18) 1.1847(15) 0.2698(5) 0.238(7) Uani 1 1 d . . . . .
H73 H -0.517017 1.130340 0.292768 0.286 Uiso 1 1 calc R U . . .
H74 H -0.565535 1.128652 0.248084 0.286 Uiso 1 1 calc R U . . .
C01O C -0.2506(18) 1.0818(12) 0.2299(4) 0.196(5) Uani 1 1 d . . . . .
H75 H -0.261261 1.144583 0.208943 0.235 Uiso 1 1 calc R U . . .
H76 H -0.345522 1.026521 0.227103 0.235 Uiso 1 1 calc R U . . .
C01P C 0.1826(10) 0.6749(12) 0.1542(4) 0.207(6) Uani 1 1 d . . . . .
H77 H 0.235313 0.667577 0.180427 0.249 Uiso 1 1 calc R U . . .
H78 H 0.134503 0.590801 0.147449 0.249 Uiso 1 1 calc R U . . .
C01Q C 0.5707(10) 0.8044(9) 0.3187(2) 0.147(3) Uani 1 1 d . . . . .
H79 H 0.671018 0.819933 0.307722 0.177 Uiso 1 1 calc R U . . .
H80 H 0.530105 0.888686 0.325634 0.177 Uiso 1 1 calc R U . . .
C01R C -0.0941(14) 0.9324(11) 0.1915(3) 0.171(4) Uani 1 1 d . . . . .
H81 H -0.100538 0.996145 0.170830 0.206 Uiso 1 1 calc R U . . .
H82 H -0.188053 0.876565 0.186879 0.206 Uiso 1 1 calc R U . . .
C22 C 1.2577(16) 0.7369(15) 0.6203(4) 0.220(5) Uani 1 1 d . . . . .
H83 H 1.168159 0.696408 0.630755 0.330 Uiso 1 1 calc R U . . .
H84 H 1.299311 0.805984 0.637186 0.330 Uiso 1 1 calc R U . . .
H85 H 1.340811 0.673417 0.618225 0.330 Uiso 1 1 calc R U . . .
C01T C -0.104(2) 0.9998(17) 0.2269(4) 0.231(6) Uani 1 1 d . . . . .
H86 H -0.009508 1.055549 0.231565 0.278 Uiso 1 1 calc R U . . .
H87 H -0.096757 0.935935 0.247631 0.278 Uiso 1 1 calc R U . . .
C23 C -0.6508(14) 1.2733(13) 0.2740(4) 0.227(6) Uani 1 1 d . . . . .
H88 H -0.607417 1.345571 0.289281 0.341 Uiso 1 1 calc R U . . .
H89 H -0.734048 1.232171 0.286619 0.341 Uiso 1 1 calc R U . . .
H90 H -0.695109 1.303859 0.248941 0.341 Uiso 1 1 calc R U . . .
C01V C 1.8746(13) 0.5025(14) 0.6667(3) 0.213(5) Uani 1 1 d . . . . .
H91 H 1.926874 0.585548 0.665693 0.320 Uiso 1 1 calc R U . . .
H92 H 1.944667 0.443074 0.681815 0.320 Uiso 1 1 calc R U . . .
H93 H 1.776204 0.512435 0.678326 0.320 Uiso 1 1 calc R U . . .
C01W C -0.243(3) 1.1483(16) 0.2655(4) 0.261(8) Uani 1 1 d . . . . .
H94 H -0.145380 1.200285 0.269373 0.314 Uiso 1 1 calc R U . . .
H95 H -0.241967 1.086620 0.286635 0.314 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 C00D 1.721(3) . ?
S001 C007 1.730(3) . ?
S002 O003 1.479(2) . ?
S002 C00D 1.748(4) . ?
S002 C011 1.817(4) . ?
C004 C20 1.404(5) . ?
C004 C00B 1.420(4) . ?
C004 C00G 1.427(4) . ?
C005 C20 1.380(5) . ?
C005 C00K 1.431(5) . ?
C005 C008 1.483(5) . ?
O006 C019 1.378(8) . ?
O006 C00R 1.397(5) . ?
C007 C21 1.366(4) . ?
C007 C00F 1.446(5) . ?
C008 C00L 1.358(5) . ?
C008 C00Q 1.410(5) . ?
C21 C00C 1.405(5) . ?
C00B C00H 1.387(5) . ?
C00B C00O 1.414(4) . ?
C00C C00D 1.364(4) . ?
C00C C00M 1.512(5) . ?
O00E C00W 1.340(5) . ?
O00E C00P 1.367(5) . ?
C00F C00H 1.382(4) . ?
C00F C00I 1.421(5) . ?
C00G C00I 1.345(5) . ?
O10 C00U 1.362(5) . ?
O10 C014 1.432(5) . ?
C00K C00O 1.336(5) . ?
C00L C00U 1.387(6) . ?
C00M C00N 1.522(6) . ?
C00N C00T 1.536(6) . ?
C00P C00R 1.368(6) . ?
C00P C00Q 1.380(6) . ?
C00R C00U 1.391(6) . ?
C00S C00V 1.510(6) . ?
C00S C011 1.520(6) . ?
C00T C00V 1.517(7) . ?
C00W C00Z 1.505(6) . ?
C00X C013 1.513(7) . ?
C00X C017 1.514(7) . ?
C00Y C018 1.500(8) . ?
C00Y C012 1.507(7) . ?
C00Z C01P 1.359(10) . ?
C010 C017 1.509(7) . ?
C010 C012 1.516(7) . ?
C013 C014 1.503(6) . ?
C015 C016 1.499(9) . ?
C015 C018 1.503(7) . ?
C016 C01M 1.543(10) . ?
C019 C01J 1.509(10) . ?
C01A C01F 1.430(10) . ?
C01A C01D 1.475(9) . ?
C01B C22 1.397(13) . ?
C01B C01E 1.469(11) . ?
C01C C01E 1.394(11) . ?
C01C C01F 1.485(9) . ?
C01D C01G 1.430(10) . ?
C01G C01L 1.471(9) . ?
C01H C01I 1.415(14) . ?
C01H C01P 1.500(11) . ?
C01I C01R 1.544(14) . ?
C01J C01Q 1.501(10) . ?
C01K C01N 1.339(16) . ?
C01K C01W 1.45(2) . ?
C01L C01Q 1.480(11) . ?
C01M C01V 1.463(13) . ?
C01N C23 1.379(15) . ?
C01O C01W 1.408(18) . ?
C01O C01T 1.500(18) . ?
C01R C01T 1.421(18) . ?

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
C00D S001 C007 91.57(15) . . ?
O003 S002 C00D 107.37(16) . . ?
O003 S002 C011 104.55(19) . . ?
C00D S002 C011 96.87(16) . . ?
C20 C004 C00B 119.7(3) . . ?
C20 C004 C00G 123.2(3) . . ?
C00B C004 C00G 117.2(3) . . ?
C20 C005 C00K 116.9(3) . . ?
C20 C005 C008 122.1(3) . . ?
C00K C005 C008 121.0(3) . . ?
C019 O006 C00R 112.2(5) . . ?
C21 C007 C00F 131.0(3) . . ?
C21 C007 S001 109.7(2) . . ?
C00F C007 S001 119.3(2) . . ?
C00L C008 C00Q 118.9(3) . . ?
C00L C008 C005 121.6(3) . . ?
C00Q C008 C005 119.5(3) . . ?
C005 C20 C004 122.1(3) . . ?
C007 C21 C00C 115.3(3) . . ?
C00H C00B C00O 122.9(3) . . ?
C00H C00B C004 119.6(3) . . ?
C00O C00B C004 117.5(3) . . ?
C00D C00C C21 110.8(3) . . ?
C00D C00C C00M 124.8(3) . . ?
C21 C00C C00M 124.3(3) . . ?
C00C C00D S001 112.6(3) . . ?
C00C C00D S002 127.7(3) . . ?
S001 C00D S002 119.25(17) . . ?
C00W O00E C00P 121.2(4) . . ?
C00H C00F C00I 117.2(3) . . ?
C00H C00F C007 121.9(3) . . ?
C00I C00F C007 120.9(3) . . ?
C00I C00G C004 121.6(3) . . ?
C00F C00H C00B 122.8(3) . . ?
C00G C00I C00F 121.6(3) . . ?
C00U O10 C014 118.5(3) . . ?
C00O C00K C005 122.1(3) . . ?
C008 C00L C00U 121.5(3) . . ?
C00C C00M C00N 115.0(3) . . ?
C00M C00N C00T 116.4(3) . . ?
C00K C00O C00B 121.7(3) . . ?
O00E C00P C00R 115.1(4) . . ?
O00E C00P C00Q 123.2(4) . . ?
C00R C00P C00Q 121.7(4) . . ?
C00P C00Q C008 119.2(3) . . ?
C00P C00R C00U 118.8(4) . . ?
C00P C00R O006 121.3(4) . . ?
C00U C00R O006 119.6(4) . . ?
C00V C00S C011 116.7(4) . . ?
C00V C00T C00N 116.1(4) . . ?
O10 C00U C00L 125.4(4) . . ?
O10 C00U C00R 114.7(4) . . ?
C00L C00U C00R 119.9(3) . . ?
C00S C00V C00T 116.8(4) . . ?
O00E C00W C00Z 108.9(4) . . ?
C013 C00X C017 112.8(4) . . ?
C018 C00Y C012 115.0(5) . . ?
C01P C00Z C00W 117.2(6) . . ?
C017 C010 C012 113.2(5) . . ?
C00S C011 S002 117.9(3) . . ?
C00Y C012 C010 114.2(5) . . ?
C014 C013 C00X 112.1(4) . . ?
O10 C014 C013 106.2(4) . . ?
C016 C015 C018 115.2(6) . . ?
C015 C016 C01M 111.1(7) . . ?
C010 C017 C00X 114.3(5) . . ?
C00Y C018 C015 114.6(5) . . ?
O006 C019 C01J 108.9(6) . . ?
C01F C01A C01D 122.3(7) . . ?
C22 C01B C01E 125.4(11) . . ?
C01E C01C C01F 123.3(8) . . ?
C01G C01D C01A 120.9(7) . . ?
C01C C01E C01B 122.8(9) . . ?
C01A C01F C01C 120.9(8) . . ?
C01D C01G C01L 122.4(7) . . ?
C01I C01H C01P 114.0(9) . . ?
C01H C01I C01R 112.9(8) . . ?
C01Q C01J C019 114.8(6) . . ?
C01N C01K C01W 121.9(17) . . ?
C01G C01L C01Q 119.0(7) . . ?
C01V C01M C016 114.3(9) . . ?
C01K C01N C23 117.6(15) . . ?
C01W C01O C01T 112.0(15) . . ?
C00Z C01P C01H 120.0(8) . . ?
C01L C01Q C01J 119.9(8) . . ?
C01T C01R C01I 116.7(11) . . ?
C01R C01T C01O 117.2(12) . . ?
C01O C01W C01K 107.6(14) . . ?

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
C00D S001 C007 C21 -0.4(3) . . . . ?
C00D S001 C007 C00F -179.8(3) . . . . ?
C20 C005 C008 C00L -25.1(6) . . . . ?
C00K C005 C008 C00L 154.3(4) . . . . ?
C20 C005 C008 C00Q 154.4(4) . . . . ?
C00K C005 C008 C00Q -26.2(6) . . . . ?
C00K C005 C20 C004 0.1(5) . . . . ?
C008 C005 C20 C004 179.5(3) . . . . ?
C00B C004 C20 C005 -0.8(5) . . . . ?
C00G C004 C20 C005 179.4(4) . . . . ?
C00F C007 C21 C00C 178.3(3) . . . . ?
S001 C007 C21 C00C -1.0(4) . . . . ?
C20 C004 C00B C00H -179.8(3) . . . . ?
C00G C004 C00B C00H -0.1(5) . . . . ?
C20 C004 C00B C00O 1.3(5) . . . . ?
C00G C004 C00B C00O -178.9(3) . . . . ?
C007 C21 C00C C00D 2.2(4) . . . . ?
C007 C21 C00C C00M 179.4(3) . . . . ?
C21 C00C C00D S001 -2.5(4) . . . . ?
C00M C00C C00D S001 -179.6(3) . . . . ?
C21 C00C C00D S002 169.6(3) . . . . ?
C00M C00C C00D S002 -7.5(5) . . . . ?
C007 S001 C00D C00C 1.7(3) . . . . ?
C007 S001 C00D S002 -171.1(2) . . . . ?
O003 S002 C00D C00C 154.8(3) . . . . ?
C011 S002 C00D C00C -97.6(3) . . . . ?
O003 S002 C00D S001 -33.7(3) . . . . ?
C011 S002 C00D S001 74.0(2) . . . . ?
C21 C007 C00F C00H -160.3(4) . . . . ?
S001 C007 C00F C00H 18.9(4) . . . . ?
C21 C007 C00F C00I 21.1(5) . . . . ?
S001 C007 C00F C00I -159.7(3) . . . . ?
C20 C004 C00G C00I 178.3(4) . . . . ?
C00B C004 C00G C00I -1.4(6) . . . . ?
C00I C00F C00H C00B -0.8(5) . . . . ?
C007 C00F C00H C00B -179.5(3) . . . . ?
C00O C00B C00H C00F 180.0(3) . . . . ?
C004 C00B C00H C00F 1.2(5) . . . . ?
C004 C00G C00I C00F 1.8(6) . . . . ?
C00H C00F C00I C00G -0.7(5) . . . . ?
C007 C00F C00I C00G 178.0(3) . . . . ?
C20 C005 C00K C00O 0.0(5) . . . . ?
C008 C005 C00K C00O -179.4(4) . . . . ?
C00Q C008 C00L C00U 0.0(7) . . . . ?
C005 C008 C00L C00U 179.5(4) . . . . ?
C00D C00C C00M C00N 86.1(4) . . . . ?
C21 C00C C00M C00N -90.6(4) . . . . ?
C00C C00M C00N C00T -82.7(4) . . . . ?
C005 C00K C00O C00B 0.5(6) . . . . ?
C00H C00B C00O C00K 180.0(3) . . . . ?
C004 C00B C00O C00K -1.2(5) . . . . ?
C00W O00E C00P C00R -175.3(6) . . . . ?
C00W O00E C00P C00Q 7.6(9) . . . . ?
O00E C00P C00Q C008 178.1(5) . . . . ?
C00R C00P C00Q C008 1.2(8) . . . . ?
C00L C008 C00Q C00P -0.6(7) . . . . ?
C005 C008 C00Q C00P 179.9(4) . . . . ?
O00E C00P C00R C00U -178.3(5) . . . . ?
C00Q C00P C00R C00U -1.2(9) . . . . ?
O00E C00P C00R O006 -4.7(8) . . . . ?
C00Q C00P C00R O006 172.4(5) . . . . ?
C019 O006 C00R C00P 89.2(7) . . . . ?
C019 O006 C00R C00U -97.3(6) . . . . ?
C00M C00N C00T C00V 109.3(4) . . . . ?
C014 O10 C00U C00L -3.9(8) . . . . ?
C014 O10 C00U C00R 176.0(5) . . . . ?
C008 C00L C00U O10 179.9(5) . . . . ?
C008 C00L C00U C00R 0.0(8) . . . . ?
C00P C00R C00U O10 -179.4(6) . . . . ?
O006 C00R C00U O10 7.0(8) . . . . ?
C00P C00R C00U C00L 0.5(8) . . . . ?
O006 C00R C00U C00L -173.1(5) . . . . ?
C011 C00S C00V C00T -66.3(6) . . . . ?
C00N C00T C00V C00S -64.7(5) . . . . ?
C00P O00E C00W C00Z 177.3(5) . . . . ?
O00E C00W C00Z C01P -62.4(10) . . . . ?
C00V C00S C011 S002 73.2(5) . . . . ?
O003 S002 C011 C00S 158.8(3) . . . . ?
C00D S002 C011 C00S 48.8(3) . . . . ?
C018 C00Y C012 C010 179.2(6) . . . . ?
C017 C010 C012 C00Y 179.5(5) . . . . ?
C017 C00X C013 C014 179.2(5) . . . . ?
C00U O10 C014 C013 -178.7(5) . . . . ?
C00X C013 C014 O10 178.1(5) . . . . ?
C018 C015 C016 C01M 177.9(6) . . . . ?
C012 C010 C017 C00X 177.4(5) . . . . ?
C013 C00X C017 C010 179.7(5) . . . . ?
C012 C00Y C018 C015 -179.4(5) . . . . ?
C016 C015 C018 C00Y 178.2(6) . . . . ?
C00R O006 C019 C01J 177.8(5) . . . . ?
C01F C01A C01D C01G 180.0(8) . . . . ?
C01F C01C C01E C01B 178.7(8) . . . . ?
C22 C01B C01E C01C -179.5(12) . . . . ?
C01D C01A C01F C01C 178.7(7) . . . . ?
C01E C01C C01F C01A -179.5(9) . . . . ?
C01A C01D C01G C01L 178.9(6) . . . . ?
C01P C01H C01I C01R -172.1(8) . . . . ?
O006 C019 C01J C01Q -62.7(9) . . . . ?
C01D C01G C01L C01Q 176.8(7) . . . . ?
C015 C016 C01M C01V -179.3(9) . . . . ?
C01W C01K C01N C23 170.4(15) . . . . ?
C00W C00Z C01P C01H 167.8(9) . . . . ?
C01I C01H C01P C00Z -106.8(13) . . . . ?
C01G C01L C01Q C01J -178.6(6) . . . . ?
C019 C01J C01Q C01L -75.8(9) . . . . ?
C01H C01I C01R C01T 171.8(11) . . . . ?
C01I C01R C01T C01O -179.9(10) . . . . ?
C01W C01O C01T C01R -177.2(14) . . . . ?
C01T C01O C01W C01K 175.9(12) . . . . ?
C01N C01K C01W C01O 78(2) . . . . ?

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_S-13_123K
_database_code_depnum_ccdc_archive 'CCDC 2127998'
loop_
_audit_author_name
_audit_author_address
'Masahiro Hayakawa'
;Department of Chemistry, Graduate School of Science, Nagoya University
Japan
;
_audit_update_record             
;
2021-12-12 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C62 H96 O4 S2'
_chemical_formula_weight         969.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.2061(2)
_cell_length_b                   10.2572(2)
_cell_length_c                   33.9910(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.477(3)
_cell_angle_gamma                90
_cell_volume                     2855.81(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    11993
_cell_measurement_theta_min      2.3670
_cell_measurement_theta_max      29.2090

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37880
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         1.801
_diffrn_reflns_theta_max         27.103
_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 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             12516
_reflns_number_gt                9947
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.879
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.989

_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       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0592P)²] 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_abs_structure_details 
;
 Flack x determined using 3826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         12516
_refine_ls_number_parameters     616
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.002
_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
S001 S -0.53456(10) -0.27186(8) 1.02869(2) 0.02046(19) Uani 1 1 d . . . . .
S002 S -0.35746(10) -0.10420(8) 0.97242(2) 0.01942(18) Uani 1 1 d . . . . .
O003 O 0.3881(3) 0.7018(2) 0.75407(6) 0.0228(5) Uani 1 1 d . . . . .
O004 O 0.5135(3) 0.6242(2) 0.82444(7) 0.0290(6) Uani 1 1 d . . . . .
O005 O 0.1283(3) 0.5860(2) 0.71934(7) 0.0276(6) Uani 1 1 d . . . . .
O006 O -0.3668(3) -0.2921(3) 1.04705(7) 0.0319(6) Uani 1 1 d . . . . .
C007 C -0.1912(4) 0.1977(3) 0.85260(9) 0.0188(7) Uani 1 1 d . . . . .
C008 C -0.1055(4) 0.2880(3) 0.83009(9) 0.0202(7) Uani 1 1 d . . . . .
H1 H -0.162134 0.331810 0.808773 0.024 Uiso 1 1 calc R U . . .
C009 C -0.6269(4) -0.2189(3) 0.94990(9) 0.0183(7) Uani 1 1 d . . . . .
C00A C -0.1062(4) 0.1326(3) 0.88468(9) 0.0175(7) Uani 1 1 d . . . . .
C00B C 0.0591(4) 0.3144(3) 0.83827(9) 0.0193(7) Uani 1 1 d . . . . .
C00C C -0.3596(4) 0.1698(3) 0.84517(10) 0.0232(8) Uani 1 1 d . . . . .
H2 H -0.418294 0.212165 0.823872 0.028 Uiso 1 1 calc R U . . .
C00D C 0.3741(4) 0.5629(3) 0.81065(10) 0.0213(7) Uani 1 1 d . . . . .
C00E C -0.4427(4) -0.0693(3) 0.92572(9) 0.0177(7) Uani 1 1 d . . . . .
C00F C -0.5848(4) -0.1364(3) 0.91828(9) 0.0188(7) Uani 1 1 d . . . . .
H3 H -0.649704 -0.128869 0.894269 0.023 Uiso 1 1 calc R U . . .
C00G C -0.1915(4) 0.0453(3) 0.90790(10) 0.0186(7) Uani 1 1 d . . . . .
H4 H -0.134624 0.002556 0.929392 0.022 Uiso 1 1 calc R U . . .
C00H C 0.2917(4) 0.4688(3) 0.83149(10) 0.0216(7) Uani 1 1 d . . . . .
H5 H 0.333481 0.443079 0.856989 0.026 Uiso 1 1 calc R U . . .
C00I C 0.1485(4) 0.4122(3) 0.81515(9) 0.0194(7) Uani 1 1 d . . . . .
C00J C 0.0619(4) 0.1604(3) 0.89262(10) 0.0200(7) Uani 1 1 d . . . . .
H6 H 0.120392 0.117806 0.913902 0.024 Uiso 1 1 calc R U . . .
C00K C 0.0900(4) 0.4504(3) 0.77745(10) 0.0214(7) Uani 1 1 d . . . . .
H7 H -0.007009 0.412275 0.765932 0.026 Uiso 1 1 calc R U . . .
C00L C 0.1729(4) 0.5444(3) 0.75652(9) 0.0211(7) Uani 1 1 d . . . . .
C00M C -0.5159(4) -0.2102(3) 0.98098(9) 0.0169(7) Uani 1 1 d . . . . .
C00N C 0.3143(4) 0.6020(3) 0.77340(10) 0.0214(7) Uani 1 1 d . . . . .
C00O C -0.4995(5) 0.5042(4) 0.50209(11) 0.0269(8) Uani 1 1 d . . . . .
H8 H -0.599970 0.516439 0.516365 0.032 Uiso 1 1 calc R U . . .
H9 H -0.480194 0.409273 0.499884 0.032 Uiso 1 1 calc R U . . .
C00P C -0.1686(4) 0.5163(4) 0.63373(10) 0.0270(8) Uani 1 1 d . . . . .
H10 H -0.150180 0.421086 0.632493 0.032 Uiso 1 1 calc R U . . .
H11 H -0.270714 0.530988 0.647175 0.032 Uiso 1 1 calc R U . . .
C00Q C 0.1404(4) 0.2471(3) 0.87027(9) 0.0207(7) Uani 1 1 d . . . . .
H12 H 0.253183 0.263195 0.876219 0.025 Uiso 1 1 calc R U . . .
C00R C 1.3898(4) 1.2629(4) 0.72957(11) 0.0290(8) Uani 1 1 d . . . . .
H13 H 1.366576 1.323530 0.707263 0.035 Uiso 1 1 calc R U . . .
H14 H 1.394519 1.314924 0.754159 0.035 Uiso 1 1 calc R U . . .
C00S C -0.3318(4) 0.5081(4) 0.56776(10) 0.0274(8) Uani 1 1 d . . . . .
H15 H -0.433097 0.520671 0.581720 0.033 Uiso 1 1 calc R U . . .
H16 H -0.312414 0.413090 0.565764 0.033 Uiso 1 1 calc R U . . .
C00T C -0.4394(4) 0.0838(3) 0.86781(10) 0.0216(7) Uani 1 1 d . . . . .
H17 H -0.551921 0.066305 0.861861 0.026 Uiso 1 1 calc R U . . .
C00U C 0.7183(4) 0.6885(3) 0.87185(10) 0.0239(8) Uani 1 1 d . . . . .
H18 H 0.740051 0.699794 0.900615 0.029 Uiso 1 1 calc R U . . .
H19 H 0.694183 0.775476 0.860303 0.029 Uiso 1 1 calc R U . . .
C00V C -0.3557(4) 0.0200(3) 0.90027(9) 0.0172(7) Uani 1 1 d . . . . .
C00W C 1.2599(4) 1.0800(4) 0.76745(10) 0.0288(8) Uani 1 1 d . . . . .
H20 H 1.271845 1.137051 0.790939 0.035 Uiso 1 1 calc R U . . .
H21 H 1.358875 1.024918 0.767192 0.035 Uiso 1 1 calc R U . . .
C00X C 0.5709(4) 0.6019(3) 0.86455(10) 0.0234(8) Uani 1 1 d . . . . .
H22 H 0.601089 0.509227 0.868594 0.028 Uiso 1 1 calc R U . . .
H23 H 0.485357 0.624632 0.882701 0.028 Uiso 1 1 calc R U . . .
C00Y C -0.7786(4) -0.3027(3) 0.94887(10) 0.0224(7) Uani 1 1 d . . . . .
H24 H -0.754953 -0.381905 0.964857 0.027 Uiso 1 1 calc R U . . .
H25 H -0.804844 -0.330995 0.921361 0.027 Uiso 1 1 calc R U . . .
C00Z C -0.7060(4) 0.5522(4) 0.39623(10) 0.0271(8) Uani 1 1 d . . . . .
H26 H -0.608023 0.540952 0.380961 0.032 Uiso 1 1 calc R U . . .
H27 H -0.728879 0.646767 0.397898 0.032 Uiso 1 1 calc R U . . .
C010 C -0.0088(4) 0.5235(4) 0.69919(10) 0.0254(8) Uani 1 1 d . . . . .
H28 H -0.109036 0.540005 0.713213 0.030 Uiso 1 1 calc R U . . .
H29 H 0.009213 0.428178 0.698104 0.030 Uiso 1 1 calc R U . . .
C011 C -0.0370(5) 0.8150(4) 0.48402(11) 0.0295(8) Uani 1 1 d . . . . .
H30 H -0.012779 0.908941 0.481163 0.035 Uiso 1 1 calc R U . . .
H31 H -0.137420 0.807704 0.498591 0.035 Uiso 1 1 calc R U . . .
C012 C 1.0043(4) 0.7366(4) 0.85017(10) 0.0280(8) Uani 1 1 d . . . . .
H32 H 1.010347 0.792826 0.873885 0.034 Uiso 1 1 calc R U . . .
H33 H 1.110348 0.691092 0.849136 0.034 Uiso 1 1 calc R U . . .
C013 C -0.6712(4) 0.4985(4) 0.43747(10) 0.0269(8) Uani 1 1 d . . . . .
H34 H -0.650426 0.403737 0.435501 0.032 Uiso 1 1 calc R U . . .
H35 H -0.769962 0.510004 0.452447 0.032 Uiso 1 1 calc R U . . .
C014 C 0.1315(4) 0.8140(4) 0.54912(11) 0.0296(8) Uani 1 1 d . . . . .
H36 H 0.028720 0.808856 0.562856 0.036 Uiso 1 1 calc R U . . .
H37 H 0.156832 0.907515 0.545580 0.036 Uiso 1 1 calc R U . . .
C015 C -0.0265(4) 0.5791(4) 0.65809(10) 0.0260(8) Uani 1 1 d . . . . .
H38 H 0.075951 0.564665 0.644776 0.031 Uiso 1 1 calc R U . . .
H39 H -0.044901 0.674295 0.659641 0.031 Uiso 1 1 calc R U . . .
C016 C 0.5232(4) 0.6613(4) 0.73200(10) 0.0274(8) Uani 1 1 d . . . . .
H40 H 0.488186 0.592868 0.712759 0.033 Uiso 1 1 calc R U . . .
H41 H 0.612009 0.625901 0.749896 0.033 Uiso 1 1 calc R U . . .
C017 C -0.5270(4) 0.5612(4) 0.46066(10) 0.0254(8) Uani 1 1 d . . . . .
H42 H -0.546555 0.656150 0.462696 0.031 Uiso 1 1 calc R U . . .
H43 H -0.427153 0.548533 0.446168 0.031 Uiso 1 1 calc R U . . .
C018 C 0.9792(4) 0.8222(4) 0.81396(11) 0.0283(8) Uani 1 1 d . . . . .
H44 H 0.879258 0.875193 0.816158 0.034 Uiso 1 1 calc R U . . .
H45 H 0.962955 0.766397 0.790296 0.034 Uiso 1 1 calc R U . . .
C019 C -0.3566(4) 0.5649(4) 0.52617(10) 0.0259(8) Uani 1 1 d . . . . .
H46 H -0.375021 0.660036 0.528172 0.031 Uiso 1 1 calc R U . . .
H47 H -0.255635 0.551648 0.512141 0.031 Uiso 1 1 calc R U . . .
C01A C -0.8505(5) 0.4847(4) 0.37469(11) 0.0333(9) Uani 1 1 d . . . . .
H48 H -0.827018 0.390168 0.373349 0.040 Uiso 1 1 calc R U . . .
H49 H -0.947659 0.495711 0.390282 0.040 Uiso 1 1 calc R U . . .
C01B C 1.1236(4) 0.9124(4) 0.80901(10) 0.0275(8) Uani 1 1 d . . . . .
H50 H 1.133252 0.972798 0.831756 0.033 Uiso 1 1 calc R U . . .
H51 H 1.224473 0.859362 0.809541 0.033 Uiso 1 1 calc R U . . .
C01C C -0.1897(4) 0.5698(4) 0.59196(10) 0.0268(8) Uani 1 1 d . . . . .
H52 H -0.087804 0.554538 0.578456 0.032 Uiso 1 1 calc R U . . .
H53 H -0.207235 0.665119 0.593201 0.032 Uiso 1 1 calc R U . . .
C01D C 1.1122(5) 0.9923(4) 0.77127(11) 0.0318(9) Uani 1 1 d . . . . .
H54 H 1.012449 1.046653 0.770737 0.038 Uiso 1 1 calc R U . . .
H55 H 1.102325 0.932476 0.748383 0.038 Uiso 1 1 calc R U . . .
C01E C -0.9301(4) -0.2346(4) 0.96429(10) 0.0279(8) Uani 1 1 d . . . . .
H56 H -0.930982 -0.142977 0.955145 0.033 Uiso 1 1 calc R U . . .
H57 H -1.028918 -0.277340 0.952113 0.033 Uiso 1 1 calc R U . . .
C01F C 0.2678(4) 0.7531(4) 0.57549(10) 0.0298(8) Uani 1 1 d . . . . .
H58 H 0.241444 0.660322 0.579976 0.036 Uiso 1 1 calc R U . . .
H59 H 0.370697 0.756309 0.561738 0.036 Uiso 1 1 calc R U . . .
C01G C -0.7424(4) -0.0456(4) 1.02895(11) 0.0307(9) Uani 1 1 d . . . . .
H60 H -0.715658 -0.037293 1.001044 0.037 Uiso 1 1 calc R U . . .
H61 H -0.745078 0.043457 1.040130 0.037 Uiso 1 1 calc R U . . .
C01H C -0.0709(5) 0.7571(4) 0.44302(11) 0.0327(9) Uani 1 1 d . . . . .
H62 H 0.027591 0.767438 0.427885 0.039 Uiso 1 1 calc R U . . .
H63 H -0.092011 0.662520 0.445620 0.039 Uiso 1 1 calc R U . . .
C01I C 1.5547(5) 1.1999(4) 0.72517(12) 0.0358(9) Uani 1 1 d . . . . .
H64 H 1.549012 1.144590 0.701264 0.043 Uiso 1 1 calc R U . . .
H65 H 1.581061 1.142886 0.748176 0.043 Uiso 1 1 calc R U . . .
C01J C -0.9424(4) -0.2348(4) 1.00908(10) 0.0279(8) Uani 1 1 d . . . . .
H66 H -1.052703 -0.265967 1.014787 0.033 Uiso 1 1 calc R U . . .
H67 H -0.862772 -0.298743 1.020584 0.033 Uiso 1 1 calc R U . . .
C01K C 0.1032(4) 0.7522(4) 0.50870(11) 0.0297(8) Uani 1 1 d . . . . .
H68 H 0.079421 0.658336 0.511960 0.036 Uiso 1 1 calc R U . . .
H69 H 0.204378 0.759524 0.494411 0.036 Uiso 1 1 calc R U . . .
C01L C 1.2503(4) 1.1648(4) 0.73075(11) 0.0290(8) Uani 1 1 d . . . . .
H70 H 1.145331 1.212702 0.729397 0.035 Uiso 1 1 calc R U . . .
H71 H 1.251315 1.108036 0.707217 0.035 Uiso 1 1 calc R U . . .
C01M C 0.4530(5) 0.8382(4) 0.68096(10) 0.0293(8) Uani 1 1 d . . . . .
H72 H 0.348199 0.845424 0.693774 0.035 Uiso 1 1 calc R U . . .
H73 H 0.487058 0.927414 0.673994 0.035 Uiso 1 1 calc R U . . .
C01N C 0.5814(4) 0.7812(4) 0.71079(11) 0.0317(9) Uani 1 1 d . . . . .
H74 H 0.679873 0.758059 0.696857 0.038 Uiso 1 1 calc R U . . .
H75 H 0.613078 0.848856 0.730559 0.038 Uiso 1 1 calc R U . . .
C01O C 0.2939(5) 0.8213(4) 0.61522(10) 0.0298(9) Uani 1 1 d . . . . .
H76 H 0.189212 0.821681 0.628222 0.036 Uiso 1 1 calc R U . . .
H77 H 0.324287 0.913183 0.610553 0.036 Uiso 1 1 calc R U . . .
C01P C -0.2142(5) 0.8190(4) 0.42023(11) 0.0371(9) Uani 1 1 d . . . . .
H78 H -0.193282 0.913663 0.417808 0.045 Uiso 1 1 calc R U . . .
H79 H -0.312712 0.808326 0.435362 0.045 Uiso 1 1 calc R U . . .
C01Q C 0.8695(4) 0.6343(4) 0.85449(11) 0.0279(8) Uani 1 1 d . . . . .
H80 H 0.838721 0.597009 0.828220 0.033 Uiso 1 1 calc R U . . .
H81 H 0.913506 0.562651 0.871511 0.033 Uiso 1 1 calc R U . . .
C01R C 1.6903(5) 1.3000(4) 0.72206(13) 0.0395(10) Uani 1 1 d . . . . .
H82 H 1.672168 1.349240 0.697482 0.059 Uiso 1 1 calc R U . . .
H83 H 1.795806 1.255180 0.722168 0.059 Uiso 1 1 calc R U . . .
H84 H 1.690175 1.359856 0.744516 0.059 Uiso 1 1 calc R U . . .
C01S C -0.8911(5) 0.5343(5) 0.33340(11) 0.0401(11) Uani 1 1 d . . . . .
H85 H -0.920661 0.626757 0.334451 0.060 Uiso 1 1 calc R U . . .
H86 H -0.982983 0.484515 0.321344 0.060 Uiso 1 1 calc R U . . .
H87 H -0.795829 0.523866 0.317631 0.060 Uiso 1 1 calc R U . . .
C01T C 0.4245(4) 0.7600(4) 0.64327(11) 0.0290(8) Uani 1 1 d . . . . .
H88 H 0.390654 0.670441 0.649917 0.035 Uiso 1 1 calc R U . . .
H89 H 0.528099 0.753950 0.629888 0.035 Uiso 1 1 calc R U . . .
C01U C -0.9130(4) -0.1050(4) 1.03013(12) 0.0350(9) Uani 1 1 d . . . . .
H90 H -0.936971 -0.116717 1.058099 0.042 Uiso 1 1 calc R U . . .
H91 H -0.992641 -0.041103 1.018562 0.042 Uiso 1 1 calc R U . . .
C01V C -0.6055(4) -0.1218(3) 1.05104(10) 0.0281(8) Uani 1 1 d . . . . .
H92 H -0.642494 -0.143918 1.077409 0.034 Uiso 1 1 calc R U . . .
H93 H -0.510522 -0.062742 1.055148 0.034 Uiso 1 1 calc R U . . .
C01W C -0.2486(6) 0.7624(5) 0.37922(12) 0.0538(13) Uani 1 1 d . . . . .
H94 H -0.154082 0.776862 0.363488 0.081 Uiso 1 1 calc R U . . .
H95 H -0.344695 0.805228 0.366486 0.081 Uiso 1 1 calc R U . . .
H96 H -0.269292 0.668616 0.381266 0.081 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 O006 1.491(2) . ?
S001 C00M 1.756(3) . ?
S001 C01V 1.828(4) . ?
S002 C00M 1.732(3) . ?
S002 C00E 1.733(3) . ?
O003 C00N 1.377(4) . ?
O003 C016 1.437(4) . ?
O004 C00D 1.363(4) . ?
O004 C00X 1.434(4) . ?
O005 C00L 1.363(4) . ?
O005 C010 1.432(4) . ?
C007 C008 1.415(5) . ?
C007 C00C 1.418(5) . ?
C007 C00A 1.425(4) . ?
C008 C00B 1.389(4) . ?
C009 C00M 1.356(4) . ?
C009 C00F 1.427(5) . ?
C009 C00Y 1.512(4) . ?
C00A C00G 1.408(4) . ?
C00A C00J 1.418(5) . ?
C00B C00Q 1.420(5) . ?
C00B C00I 1.494(5) . ?
C00C C00T 1.364(5) . ?
C00D C00N 1.389(5) . ?
C00D C00H 1.396(5) . ?
C00E C00F 1.364(4) . ?
C00E C00V 1.474(4) . ?
C00G C00V 1.381(5) . ?
C00H C00I 1.395(4) . ?
C00I C00K 1.397(5) . ?
C00J C00Q 1.357(5) . ?
C00K C00L 1.398(5) . ?
C00L C00N 1.394(5) . ?
C00O C019 1.522(5) . ?
C00O C017 1.529(5) . ?
C00P C01C 1.522(5) . ?
C00P C015 1.530(5) . ?
C00R C01I 1.515(5) . ?
C00R C01L 1.527(5) . ?
C00S C01C 1.524(5) . ?
C00S C019 1.532(5) . ?
C00T C00V 1.423(5) . ?
C00U C00X 1.509(5) . ?
C00U C01Q 1.512(5) . ?
C00W C01L 1.519(5) . ?
C00W C01D 1.521(5) . ?
C00Y C01E 1.545(5) . ?
C00Z C013 1.517(5) . ?
C00Z C01A 1.522(5) . ?
C010 C015 1.508(5) . ?
C011 C01K 1.524(5) . ?
C011 C01H 1.525(5) . ?
C012 C018 1.516(5) . ?
C012 C01Q 1.538(5) . ?
C013 C017 1.524(5) . ?
C014 C01K 1.518(5) . ?
C014 C01F 1.524(5) . ?
C016 C01N 1.517(5) . ?
C018 C01B 1.521(5) . ?
C01A C01S 1.511(5) . ?
C01B C01D 1.520(5) . ?
C01E C01J 1.532(5) . ?
C01F C01O 1.524(5) . ?
C01G C01V 1.528(5) . ?
C01G C01U 1.529(5) . ?
C01H C01P 1.509(5) . ?
C01I C01R 1.522(5) . ?
C01J C01U 1.524(6) . ?
C01M C01T 1.517(5) . ?
C01M C01N 1.533(5) . ?
C01O C01T 1.526(5) . ?
C01P C01W 1.521(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
O006 S001 C00M 107.85(15) . . ?
O006 S001 C01V 104.64(16) . . ?
C00M S001 C01V 97.37(15) . . ?
C00M S002 C00E 91.04(16) . . ?
C00N O003 C016 114.2(3) . . ?
C00D O004 C00X 118.3(3) . . ?
C00L O005 C010 117.5(3) . . ?
C008 C007 C00C 123.1(3) . . ?
C008 C007 C00A 118.9(3) . . ?
C00C C007 C00A 117.9(3) . . ?
C00B C008 C007 121.9(3) . . ?
C00M C009 C00F 111.5(3) . . ?
C00M C009 C00Y 124.7(3) . . ?
C00F C009 C00Y 123.8(3) . . ?
C00G C00A C00J 122.2(3) . . ?
C00G C00A C007 119.3(3) . . ?
C00J C00A C007 118.5(3) . . ?
C008 C00B C00Q 117.7(3) . . ?
C008 C00B C00I 121.9(3) . . ?
C00Q C00B C00I 120.5(3) . . ?
C00T C00C C007 121.7(3) . . ?
O004 C00D C00N 115.0(3) . . ?
O004 C00D C00H 124.5(3) . . ?
C00N C00D C00H 120.5(3) . . ?
C00F C00E C00V 130.1(3) . . ?
C00F C00E S002 111.0(2) . . ?
C00V C00E S002 118.9(2) . . ?
C00E C00F C009 113.7(3) . . ?
C00V C00G C00A 121.8(3) . . ?
C00I C00H C00D 120.5(3) . . ?
C00H C00I C00K 118.9(3) . . ?
C00H C00I C00B 119.9(3) . . ?
C00K C00I C00B 121.2(3) . . ?
C00Q C00J C00A 120.9(3) . . ?
C00I C00K C00L 120.6(3) . . ?
O005 C00L C00N 114.8(3) . . ?
O005 C00L C00K 125.2(3) . . ?
C00N C00L C00K 120.1(3) . . ?
C009 C00M S002 112.7(2) . . ?
C009 C00M S001 127.1(3) . . ?
S002 C00M S001 119.32(18) . . ?
O003 C00N C00D 120.6(3) . . ?
O003 C00N C00L 119.9(3) . . ?
C00D C00N C00L 119.5(3) . . ?
C019 C00O C017 113.9(3) . . ?
C01C C00P C015 113.1(3) . . ?
C00J C00Q C00B 122.1(3) . . ?
C01I C00R C01L 113.4(3) . . ?
C01C C00S C019 113.2(3) . . ?
C00C C00T C00V 120.6(3) . . ?
C00X C00U C01Q 112.9(3) . . ?
C00G C00V C00T 118.6(3) . . ?
C00G C00V C00E 120.6(3) . . ?
C00T C00V C00E 120.8(3) . . ?
C01L C00W C01D 114.0(3) . . ?
O004 C00X C00U 106.0(3) . . ?
C009 C00Y C01E 114.4(3) . . ?
C013 C00Z C01A 112.1(3) . . ?
O005 C010 C015 107.6(3) . . ?
C01K C011 C01H 115.4(3) . . ?
C018 C012 C01Q 114.2(3) . . ?
C00Z C013 C017 114.9(3) . . ?
C01K C014 C01F 115.3(3) . . ?
C010 C015 C00P 111.7(3) . . ?
O003 C016 C01N 106.8(3) . . ?
C013 C017 C00O 112.5(3) . . ?
C012 C018 C01B 112.0(3) . . ?
C00O C019 C00S 113.3(3) . . ?
C01S C01A C00Z 114.5(3) . . ?
C01D C01B C018 114.4(3) . . ?
C00P C01C C00S 113.2(3) . . ?
C01B C01D C00W 112.5(3) . . ?
C01J C01E C00Y 116.1(3) . . ?
C01O C01F C014 113.1(3) . . ?
C01V C01G C01U 115.5(3) . . ?
C01P C01H C011 113.5(3) . . ?
C00R C01I C01R 112.3(3) . . ?
C01U C01J C01E 116.6(3) . . ?
C014 C01K C011 113.0(3) . . ?
C00W C01L C00R 113.4(3) . . ?
C01T C01M C01N 114.9(3) . . ?
C016 C01N C01M 113.6(3) . . ?
C01F C01O C01T 114.8(3) . . ?
C01H C01P C01W 113.9(4) . . ?
C00U C01Q C012 113.5(3) . . ?
C01M C01T C01O 112.1(3) . . ?
C01J C01U C01G 117.1(3) . . ?
C01G C01V S001 118.0(2) . . ?

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
C00C C007 C008 C00B 179.4(3) . . . . ?
C00A C007 C008 C00B 0.3(5) . . . . ?
C008 C007 C00A C00G 178.3(3) . . . . ?
C00C C007 C00A C00G -0.8(5) . . . . ?
C008 C007 C00A C00J -0.4(4) . . . . ?
C00C C007 C00A C00J -179.5(3) . . . . ?
C007 C008 C00B C00Q 0.1(5) . . . . ?
C007 C008 C00B C00I -178.4(3) . . . . ?
C008 C007 C00C C00T -178.9(3) . . . . ?
C00A C007 C00C C00T 0.1(5) . . . . ?
C00X O004 C00D C00N 172.0(3) . . . . ?
C00X O004 C00D C00H -7.1(5) . . . . ?
C00M S002 C00E C00F 0.3(3) . . . . ?
C00M S002 C00E C00V -177.9(3) . . . . ?
C00V C00E C00F C009 177.1(3) . . . . ?
S002 C00E C00F C009 -0.8(4) . . . . ?
C00M C009 C00F C00E 1.1(4) . . . . ?
C00Y C009 C00F C00E 179.8(3) . . . . ?
C00J C00A C00G C00V 179.1(3) . . . . ?
C007 C00A C00G C00V 0.5(5) . . . . ?
O004 C00D C00H C00I 179.3(3) . . . . ?
C00N C00D C00H C00I 0.3(5) . . . . ?
C00D C00H C00I C00K 0.6(5) . . . . ?
C00D C00H C00I C00B -178.3(3) . . . . ?
C008 C00B C00I C00H 158.0(3) . . . . ?
C00Q C00B C00I C00H -20.5(5) . . . . ?
C008 C00B C00I C00K -20.8(5) . . . . ?
C00Q C00B C00I C00K 160.7(3) . . . . ?
C00G C00A C00J C00Q -178.6(3) . . . . ?
C007 C00A C00J C00Q 0.0(5) . . . . ?
C00H C00I C00K C00L -0.4(5) . . . . ?
C00B C00I C00K C00L 178.5(3) . . . . ?
C010 O005 C00L C00N 175.4(3) . . . . ?
C010 O005 C00L C00K -3.7(5) . . . . ?
C00I C00K C00L O005 178.3(3) . . . . ?
C00I C00K C00L C00N -0.8(5) . . . . ?
C00F C009 C00M S002 -0.8(4) . . . . ?
C00Y C009 C00M S002 -179.5(3) . . . . ?
C00F C009 C00M S001 168.5(2) . . . . ?
C00Y C009 C00M S001 -10.2(5) . . . . ?
C00E S002 C00M C009 0.3(3) . . . . ?
C00E S002 C00M S001 -170.0(2) . . . . ?
O006 S001 C00M C009 155.7(3) . . . . ?
C01V S001 C00M C009 -96.3(3) . . . . ?
O006 S001 C00M S002 -35.5(2) . . . . ?
C01V S001 C00M S002 72.5(2) . . . . ?
C016 O003 C00N C00D 85.8(4) . . . . ?
C016 O003 C00N C00L -97.8(4) . . . . ?
O004 C00D C00N O003 -4.1(5) . . . . ?
C00H C00D C00N O003 175.0(3) . . . . ?
O004 C00D C00N C00L 179.5(3) . . . . ?
C00H C00D C00N C00L -1.4(5) . . . . ?
O005 C00L C00N O003 6.1(5) . . . . ?
C00K C00L C00N O003 -174.7(3) . . . . ?
O005 C00L C00N C00D -177.5(3) . . . . ?
C00K C00L C00N C00D 1.6(5) . . . . ?
C00A C00J C00Q C00B 0.4(5) . . . . ?
C008 C00B C00Q C00J -0.5(5) . . . . ?
C00I C00B C00Q C00J 178.0(3) . . . . ?
C007 C00C C00T C00V 0.8(5) . . . . ?
C00A C00G C00V C00T 0.5(5) . . . . ?
C00A C00G C00V C00E -178.4(3) . . . . ?
C00C C00T C00V C00G -1.1(5) . . . . ?
C00C C00T C00V C00E 177.7(3) . . . . ?
C00F C00E C00V C00G -159.0(3) . . . . ?
S002 C00E C00V C00G 18.8(4) . . . . ?
C00F C00E C00V C00T 22.2(5) . . . . ?
S002 C00E C00V C00T -160.1(3) . . . . ?
C00D O004 C00X C00U -176.3(3) . . . . ?
C01Q C00U C00X O004 -77.6(4) . . . . ?
C00M C009 C00Y C01E 89.0(4) . . . . ?
C00F C009 C00Y C01E -89.5(4) . . . . ?
C00L O005 C010 C015 -176.1(3) . . . . ?
C01A C00Z C013 C017 179.6(3) . . . . ?
O005 C010 C015 C00P 178.9(3) . . . . ?
C01C C00P C015 C010 -179.7(3) . . . . ?
C00N O003 C016 C01N 176.4(3) . . . . ?
C00Z C013 C017 C00O 179.3(3) . . . . ?
C019 C00O C017 C013 -179.8(3) . . . . ?
C01Q C012 C018 C01B -174.5(3) . . . . ?
C017 C00O C019 C00S 179.3(3) . . . . ?
C01C C00S C019 C00O -179.5(3) . . . . ?
C013 C00Z C01A C01S 180.0(3) . . . . ?
C012 C018 C01B C01D 174.9(3) . . . . ?
C015 C00P C01C C00S -179.6(3) . . . . ?
C019 C00S C01C C00P 178.1(3) . . . . ?
C018 C01B C01D C00W -179.5(3) . . . . ?
C01L C00W C01D C01B -178.0(3) . . . . ?
C009 C00Y C01E C01J -82.9(4) . . . . ?
C01K C014 C01F C01O 178.4(3) . . . . ?
C01K C011 C01H C01P 178.0(3) . . . . ?
C01L C00R C01I C01R 177.2(3) . . . . ?
C00Y C01E C01J C01U 108.1(4) . . . . ?
C01F C014 C01K C011 178.7(3) . . . . ?
C01H C011 C01K C014 179.9(3) . . . . ?
C01D C00W C01L C00R 173.6(3) . . . . ?
C01I C00R C01L C00W 67.4(4) . . . . ?
O003 C016 C01N C01M -62.8(4) . . . . ?
C01T C01M C01N C016 -73.8(4) . . . . ?
C014 C01F C01O C01T 177.6(3) . . . . ?
C011 C01H C01P C01W 179.7(3) . . . . ?
C00X C00U C01Q C012 162.3(3) . . . . ?
C018 C012 C01Q C00U -80.8(4) . . . . ?
C01N C01M C01T C01O 179.3(3) . . . . ?
C01F C01O C01T C01M 175.8(3) . . . . ?
C01E C01J C01U C01G -64.2(4) . . . . ?
C01V C01G C01U C01J -66.5(4) . . . . ?
C01U C01G C01V S001 74.6(4) . . . . ?
O006 S001 C01V C01G 157.8(3) . . . . ?
C00M S001 C01V C01G 47.1(3) . . . . ?

_refine_diff_density_max         0.505
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_S-10
_database_code_depnum_ccdc_archive 'CCDC 2127999'
loop_
_audit_author_name
_audit_author_address
'Masahiro Hayakawa'
;Department of Chemistry, Graduate School of Science, Nagoya University
Japan
;
_audit_update_record             
;
2021-12-12 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            (S)-oxTN-2Napt
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 O S2'
_chemical_formula_weight         340.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.44970(10)
_cell_length_b                   9.42970(10)
_cell_length_c                   12.1517(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.419(2)
_cell_angle_gamma                90
_cell_volume                     853.38(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    11140
_cell_measurement_theta_min      2.7240
_cell_measurement_theta_max      30.0500

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.314
_shelx_estimated_absorpt_T_min   0.815
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73294
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11347
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.734
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3880
_reflns_number_gt                3835
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_max     0.982
_reflns_Friedel_fraction_full    0.992

_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       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.1069P] 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_abs_structure_details 
;
 Flack x determined using 1764 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3880
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0215
_refine_ls_wR_factor_ref         0.0590
_refine_ls_wR_factor_gt          0.0589
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.78254(5) 0.29066(4) 0.56631(3) 0.01948(10) Uani 1 1 d . . . . .
S002 S 0.65480(5) 0.41100(4) 0.34659(3) 0.02050(10) Uani 1 1 d . . . . .
O003 O 0.92536(17) 0.22561(16) 0.49778(12) 0.0320(3) Uani 1 1 d . . . . .
C004 C 0.3713(2) 0.52292(18) 0.21998(13) 0.0196(3) Uani 1 1 d . . . . .
C005 C 0.1980(2) 0.57460(18) 0.20679(14) 0.0212(3) Uani 1 1 d . . . . .
H005 H 0.116543 0.564836 0.265244 0.025 Uiso 1 1 calc R U . . .
C006 C 0.1397(2) 0.64182(18) 0.10770(14) 0.0228(3) Uani 1 1 d . . . . .
C007 C 0.4336(2) 0.36728(17) 0.50446(13) 0.0180(3) Uani 1 1 d . . . . .
C008 C 0.6104(2) 0.35185(17) 0.47747(13) 0.0181(3) Uani 1 1 d . . . . .
C009 C 0.4916(2) 0.5381(2) 0.13146(14) 0.0255(4) Uani 1 1 d . . . . .
H009 H 0.610893 0.503332 0.139456 0.031 Uiso 1 1 calc R U . . .
C00A C 0.7456(2) 0.57547(18) 0.64679(14) 0.0228(3) Uani 1 1 d . . . . .
H00A H 0.808416 0.667966 0.646137 0.027 Uiso 1 1 calc R U . . .
H00B H 0.644306 0.581240 0.592665 0.027 Uiso 1 1 calc R U . . .
C00B C 0.3330(2) 0.43046(17) 0.41580(13) 0.0191(3) Uani 1 1 d . . . . .
H00C H 0.208402 0.450742 0.419618 0.023 Uiso 1 1 calc R U . . .
C00C C 0.4378(3) 0.6019(2) 0.03517(15) 0.0282(4) Uani 1 1 d . . . . .
H00D H 0.520749 0.611057 -0.022563 0.034 Uiso 1 1 calc R U . . .
C00D C -0.0353(3) 0.6989(2) 0.09431(17) 0.0311(4) Uani 1 1 d . . . . .
H00E H -0.117323 0.692014 0.152723 0.037 Uiso 1 1 calc R U . . .
C00E C -0.0877(3) 0.7640(2) -0.00235(18) 0.0373(5) Uani 1 1 d . . . . .
H00F H -0.204555 0.803703 -0.009809 0.045 Uiso 1 1 calc R U . . .
C00F C 0.5416(2) 0.4276(2) 0.77301(14) 0.0249(3) Uani 1 1 d . . . . .
H00G H 0.511237 0.418982 0.851581 0.030 Uiso 1 1 calc R U . . .
H00H H 0.606530 0.340282 0.752495 0.030 Uiso 1 1 calc R U . . .
C00G C 0.6688(3) 0.5537(2) 0.76077(15) 0.0270(4) Uani 1 1 d . . . . .
H00I H 0.603695 0.640992 0.781234 0.032 Uiso 1 1 calc R U . . .
H00J H 0.770162 0.541961 0.814200 0.032 Uiso 1 1 calc R U . . .
C00H C 0.4315(2) 0.45937(18) 0.32473(13) 0.0187(3) Uani 1 1 d . . . . .
C00I C 0.2615(3) 0.65449(19) 0.01983(14) 0.0252(4) Uani 1 1 d . . . . .
C00J C 0.3507(2) 0.32385(18) 0.61081(14) 0.0216(3) Uani 1 1 d . . . . .
H00K H 0.409089 0.235242 0.636755 0.026 Uiso 1 1 calc R U . . .
H00L H 0.222200 0.302450 0.596140 0.026 Uiso 1 1 calc R U . . .
C00K C 0.3645(2) 0.4346(2) 0.70398(14) 0.0244(4) Uani 1 1 d . . . . .
H00M H 0.262546 0.420826 0.753628 0.029 Uiso 1 1 calc R U . . .
H00N H 0.352866 0.530427 0.671356 0.029 Uiso 1 1 calc R U . . .
C00L C 0.8755(2) 0.46157(19) 0.60836(15) 0.0220(3) Uani 1 1 d . . . . .
H00O H 0.964448 0.444407 0.668766 0.026 Uiso 1 1 calc R U . . .
H00P H 0.941738 0.500618 0.545566 0.026 Uiso 1 1 calc R U . . .
C00M C 0.0314(3) 0.7722(2) -0.09063(17) 0.0381(5) Uani 1 1 d . . . . .
H00Q H -0.007171 0.814805 -0.158008 0.046 Uiso 1 1 calc R U . . .
C00N C 0.2011(3) 0.7197(2) -0.08008(15) 0.0326(4) Uani 1 1 d . . . . .
H00R H 0.280046 0.726547 -0.140029 0.039 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 O003 1.4986(13) . ?
S001 C008 1.7535(16) . ?
S001 C00L 1.8222(18) . ?
S002 C008 1.7251(16) . ?
S002 C00H 1.7393(16) . ?
C004 C005 1.385(2) . ?
C004 C009 1.424(2) . ?
C004 C00H 1.467(2) . ?
C005 C006 1.419(2) . ?
C006 C00D 1.416(3) . ?
C006 C00I 1.424(2) . ?
C007 C008 1.373(2) . ?
C007 C00B 1.427(2) . ?
C007 C00J 1.503(2) . ?
C009 C00C 1.367(3) . ?
C00A C00G 1.525(2) . ?
C00A C00L 1.527(2) . ?
C00B C00H 1.370(2) . ?
C00C C00I 1.412(3) . ?
C00D C00E 1.373(3) . ?
C00E C00M 1.411(3) . ?
C00F C00G 1.530(3) . ?
C00F C00K 1.547(2) . ?
C00I C00N 1.424(2) . ?
C00J C00K 1.542(2) . ?
C00M C00N 1.360(3) . ?

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
O003 S001 C008 108.12(8) . . ?
O003 S001 C00L 104.34(8) . . ?
C008 S001 C00L 98.55(8) . . ?
C008 S002 C00H 91.20(8) . . ?
C005 C004 C009 118.64(16) . . ?
C005 C004 C00H 120.52(15) . . ?
C009 C004 C00H 120.78(15) . . ?
C004 C005 C006 121.33(16) . . ?
C00D C006 C005 121.92(17) . . ?
C00D C006 C00I 118.96(17) . . ?
C005 C006 C00I 119.11(16) . . ?
C008 C007 C00B 110.66(14) . . ?
C008 C007 C00J 126.43(15) . . ?
C00B C007 C00J 122.91(14) . . ?
C007 C008 S002 113.15(12) . . ?
C007 C008 S001 125.39(13) . . ?
S002 C008 S001 121.33(9) . . ?
C00C C009 C004 120.95(17) . . ?
C00G C00A C00L 115.98(15) . . ?
C00H C00B C007 114.28(15) . . ?
C009 C00C C00I 121.29(17) . . ?
C00E C00D C006 120.6(2) . . ?
C00D C00E C00M 120.3(2) . . ?
C00G C00F C00K 115.86(15) . . ?
C00A C00G C00F 116.09(15) . . ?
C00B C00H C004 128.61(15) . . ?
C00B C00H S002 110.71(12) . . ?
C004 C00H S002 120.68(12) . . ?
C00C C00I C006 118.67(16) . . ?
C00C C00I C00N 122.53(18) . . ?
C006 C00I C00N 118.80(18) . . ?
C007 C00J C00K 115.19(14) . . ?
C00J C00K C00F 114.20(14) . . ?
C00A C00L S001 117.95(12) . . ?
C00N C00M C00E 120.56(19) . . ?
C00M C00N C00I 120.74(19) . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_S-9
_database_code_depnum_ccdc_archive 'CCDC 2128002'
loop_
_audit_author_name
_audit_author_address
'Masahiro Hayakawa'
;Department of Chemistry, Graduate School of Science, Nagoya University
Japan
;
_audit_update_record             
;
2021-12-12 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            (S)-oxTN-1Napt
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 O S2'
_chemical_formula_weight         340.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.23910(10)
_cell_length_b                   15.9453(2)
_cell_length_c                   7.41670(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.656(2)
_cell_angle_gamma                90
_cell_volume                     824.34(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    10801
_cell_measurement_theta_min      2.5500
_cell_measurement_theta_max      30.1100

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.325
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10819
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_av_R_equivalents  0.0111
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.555
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3763
_reflns_number_gt                3741
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.990

_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       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+0.1084P] 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_abs_structure_details 
;
 Flack x determined using 1779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3763
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0199
_refine_ls_wR_factor_ref         0.0547
_refine_ls_wR_factor_gt          0.0546
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2232(2) 0.61216(10) 0.1997(2) 0.0172(3) Uani 1 1 d . . . . .
C2 C 0.2843(3) 0.62968(11) 0.0430(2) 0.0221(3) Uani 1 1 d . . . . .
H2 H 0.399718 0.604992 0.030791 0.027 Uiso 1 1 calc R U . . .
C3 C 0.1803(3) 0.68305(12) -0.0992(2) 0.0268(4) Uani 1 1 d . . . . .
H3 H 0.228189 0.695377 -0.203571 0.032 Uiso 1 1 calc R U . . .
C4 C 0.0124(3) 0.71696(11) -0.0881(3) 0.0254(4) Uani 1 1 d . . . . .
H4 H -0.059231 0.751309 -0.187107 0.030 Uiso 1 1 calc R U . . .
C5 C -0.0577(2) 0.70164(10) 0.0704(2) 0.0201(3) Uani 1 1 d . . . . .
C6 C -0.2335(3) 0.73639(11) 0.0821(3) 0.0254(4) Uani 1 1 d . . . . .
H6 H -0.306848 0.769637 -0.018150 0.030 Uiso 1 1 calc R U . . .
C7 C -0.2994(2) 0.72274(11) 0.2360(3) 0.0254(3) Uani 1 1 d . . . . .
H7 H -0.417898 0.746513 0.241954 0.031 Uiso 1 1 calc R U . . .
C9 C -0.0223(2) 0.63791(10) 0.3768(2) 0.0184(3) Uani 1 1 d . . . . .
H9 H 0.047968 0.604301 0.477965 0.022 Uiso 1 1 calc R U . . .
C8 C -0.1919(2) 0.67348(11) 0.3860(2) 0.0223(3) Uani 1 1 d . . . . .
H8 H -0.237196 0.664962 0.493517 0.027 Uiso 1 1 calc R U . . .
C10 C 0.0504(2) 0.65028(10) 0.2194(2) 0.0162(3) Uani 1 1 d . . . . .
S11 S 0.38550(5) 0.45482(2) 0.25225(5) 0.01800(9) Uani 1 1 d . . . . .
C12 C 0.3330(2) 0.55078(10) 0.3364(2) 0.0167(3) Uani 1 1 d . . . . .
C13 C 0.3995(2) 0.55378(11) 0.5268(2) 0.0185(3) Uani 1 1 d . . . . .
H13 H 0.385888 0.601709 0.598240 0.022 Uiso 1 1 calc R U . . .
C14 C 0.4913(2) 0.47850(10) 0.6091(2) 0.0175(3) Uani 1 1 d . . . . .
C15 C 0.4942(2) 0.42000(10) 0.4756(2) 0.0166(3) Uani 1 1 d . . . . .
S16 S 0.61541(5) 0.32335(2) 0.51373(5) 0.01727(9) Uani 1 1 d . . . . .
C17 C 0.8271(3) 0.35478(11) 0.4420(3) 0.0237(3) Uani 1 1 d . . . . .
H17A H 0.924636 0.310032 0.480457 0.028 Uiso 1 1 calc R U . . .
H17B H 0.791207 0.357350 0.303519 0.028 Uiso 1 1 calc R U . . .
C18 C 0.9211(3) 0.43780(11) 0.5167(3) 0.0277(4) Uani 1 1 d . . . . .
H18A H 1.006953 0.454633 0.439297 0.033 Uiso 1 1 calc R U . . .
H18B H 0.819461 0.480921 0.499636 0.033 Uiso 1 1 calc R U . . .
C19 C 1.0367(3) 0.43835(13) 0.7210(3) 0.0340(4) Uani 1 1 d . . . . .
H19A H 1.101164 0.493485 0.747964 0.041 Uiso 1 1 calc R U . . .
H19B H 1.138487 0.395314 0.737308 0.041 Uiso 1 1 calc R U . . .
C20 C 0.9280(3) 0.42255(12) 0.8674(3) 0.0303(4) Uani 1 1 d . . . . .
H20A H 1.023260 0.414203 0.989878 0.036 Uiso 1 1 calc R U . . .
H20B H 0.855936 0.369398 0.835301 0.036 Uiso 1 1 calc R U . . .
C21 C 0.7866(3) 0.49087(12) 0.8913(3) 0.0293(4) Uani 1 1 d . . . . .
H21A H 0.812986 0.504399 1.026158 0.035 Uiso 1 1 calc R U . . .
H21B H 0.810929 0.542200 0.826227 0.035 Uiso 1 1 calc R U . . .
C22 C 0.5735(3) 0.46761(12) 0.8167(2) 0.0237(3) Uani 1 1 d . . . . .
H22A H 0.557030 0.408337 0.849031 0.028 Uiso 1 1 calc R U . . .
H22B H 0.498498 0.502523 0.881960 0.028 Uiso 1 1 calc R U . . .
O23 O 0.51300(19) 0.26356(8) 0.36469(19) 0.0263(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(2) . ?
C1 C10 1.433(2) . ?
C1 C12 1.478(2) . ?
C2 C3 1.405(3) . ?
C3 C4 1.353(3) . ?
C4 C5 1.422(2) . ?
C5 C6 1.412(3) . ?
C5 C10 1.427(2) . ?
C6 C7 1.368(3) . ?
C7 C8 1.412(3) . ?
C9 C8 1.371(2) . ?
C9 C10 1.418(2) . ?
S11 C15 1.7226(16) . ?
S11 C12 1.7330(16) . ?
C12 C13 1.364(2) . ?
C13 C14 1.427(2) . ?
C14 C15 1.365(2) . ?
C14 C22 1.504(2) . ?
C15 S16 1.7581(16) . ?
S16 O23 1.4960(13) . ?
S16 C17 1.8230(18) . ?
C17 C18 1.523(2) . ?
C18 C19 1.521(3) . ?
C19 C20 1.524(3) . ?
C20 C21 1.538(3) . ?
C21 C22 1.537(3) . ?

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 C10 119.15(15) . . ?
C2 C1 C12 118.52(15) . . ?
C10 C1 C12 122.24(13) . . ?
C1 C2 C3 121.79(16) . . ?
C4 C3 C2 120.29(16) . . ?
C3 C4 C5 120.56(16) . . ?
C6 C5 C4 120.78(16) . . ?
C6 C5 C10 119.53(15) . . ?
C4 C5 C10 119.69(16) . . ?
C7 C6 C5 120.76(16) . . ?
C6 C7 C8 120.27(16) . . ?
C8 C9 C10 121.33(15) . . ?
C9 C8 C7 120.09(16) . . ?
C9 C10 C5 117.99(15) . . ?
C9 C10 C1 123.58(14) . . ?
C5 C10 C1 118.40(14) . . ?
C15 S11 C12 91.49(8) . . ?
C13 C12 C1 131.41(14) . . ?
C13 C12 S11 110.70(12) . . ?
C1 C12 S11 117.86(11) . . ?
C12 C13 C14 114.00(15) . . ?
C15 C14 C13 111.18(14) . . ?
C15 C14 C22 125.79(15) . . ?
C13 C14 C22 123.03(14) . . ?
C14 C15 S11 112.63(12) . . ?
C14 C15 S16 125.96(13) . . ?
S11 C15 S16 121.06(9) . . ?
O23 S16 C15 108.27(8) . . ?
O23 S16 C17 104.34(8) . . ?
C15 S16 C17 97.72(8) . . ?
C18 C17 S16 117.47(13) . . ?
C19 C18 C17 116.05(16) . . ?
C18 C19 C20 117.25(15) . . ?
C19 C20 C21 116.93(17) . . ?
C22 C21 C20 114.99(15) . . ?
C14 C22 C21 114.96(15) . . ?

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_R-2
_database_code_depnum_ccdc_archive 'CCDC 2128001'
loop_
_audit_author_name
_audit_author_address
'Masahiro Hayakawa'
;Department of Chemistry, Graduate School of Science, Nagoya University
Japan
;
_audit_update_record             
;
2021-12-12 deposited with the CCDC.	2022-01-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'(R)-2-bromo-4,5,6,7,8,9-hexahydrothieno[2,3-b]thionine S-oxide'
_chemical_name_common            (R)-oxTN-Br
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 Br O S2'
_chemical_formula_weight         293.23

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.66070(10)
_cell_length_b                   9.6197(2)
_cell_length_c                   15.2085(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1120.77(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    14188
_cell_measurement_theta_min      2.5160
_cell_measurement_theta_max      30.8330

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.004
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72424
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku Saturn70 (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            15102
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.505
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2561
_reflns_number_gt                2520
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0252P)²+0.1126P] 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_abs_structure_details 
;
 Flack x determined using 1039 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2561
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0152
_refine_ls_R_factor_gt           0.0146
_refine_ls_wR_factor_ref         0.0452
_refine_ls_wR_factor_gt          0.0449
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_restrained_S_all      1.214
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.53945(3) 0.31248(2) 0.51594(2) 0.02097(8) Uani 1 1 d . . . . .
S002 S 0.22917(7) 0.57009(6) 0.19662(4) 0.01473(12) Uani 1 1 d . . . . .
S003 S 0.29537(8) 0.45255(6) 0.37853(4) 0.01675(13) Uani 1 1 d . . . . .
O004 O 0.0834(2) 0.64640(18) 0.24166(13) 0.0244(4) Uani 1 1 d . . . . .
C005 C 0.4956(3) 0.4083(2) 0.05193(16) 0.0166(5) Uani 1 1 d . . . . .
H00A H 0.432689 0.497310 0.060088 0.020 Uiso 1 1 calc R U . . .
H00B H 0.539441 0.406571 -0.009288 0.020 Uiso 1 1 calc R U . . .
C006 C 0.5491(3) 0.4853(2) 0.26670(15) 0.0140(4) Uani 1 1 d . . . . .
C007 C 0.2658(3) 0.2826(2) 0.15031(17) 0.0170(5) Uani 1 1 d . . . . .
H00C H 0.200782 0.193751 0.152436 0.020 Uiso 1 1 calc R U . . .
H00D H 0.352621 0.280870 0.198514 0.020 Uiso 1 1 calc R U . . .
C008 C 0.6546(3) 0.5202(3) 0.18629(16) 0.0161(5) Uani 1 1 d . . . . .
H00E H 0.776860 0.537320 0.204462 0.019 Uiso 1 1 calc R U . . .
H00F H 0.609090 0.607711 0.160793 0.019 Uiso 1 1 calc R U . . .
C009 C 0.3742(3) 0.5103(2) 0.27827(16) 0.0140(4) Uani 1 1 d . . . . .
C00A C 0.3642(3) 0.2896(2) 0.06278(16) 0.0186(5) Uani 1 1 d . . . . .
H00G H 0.277123 0.296869 0.014898 0.022 Uiso 1 1 calc R U . . .
H00H H 0.427177 0.200650 0.054629 0.022 Uiso 1 1 calc R U . . .
C00B C 0.6539(3) 0.4074(2) 0.11424(17) 0.0167(5) Uani 1 1 d . . . . .
H00I H 0.761017 0.418037 0.078468 0.020 Uiso 1 1 calc R U . . .
H00J H 0.659711 0.315278 0.143140 0.020 Uiso 1 1 calc R U . . .
C00C C 0.6214(3) 0.4172(2) 0.34188(16) 0.0160(5) Uani 1 1 d . . . . .
H00K H 0.740794 0.391532 0.346881 0.019 Uiso 1 1 calc R U . . .
C00D C 0.1375(3) 0.4010(2) 0.16805(17) 0.0172(5) Uani 1 1 d . . . . .
H00L H 0.059408 0.371750 0.216507 0.021 Uiso 1 1 calc R U . . .
H00M H 0.064087 0.412998 0.115023 0.021 Uiso 1 1 calc R U . . .
C00E C 0.5008(3) 0.3933(2) 0.40510(16) 0.0161(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C00E 1.880(2) . ?
S002 O004 1.5018(18) . ?
S002 C009 1.762(2) . ?
S002 C00D 1.824(2) . ?
S003 C00E 1.722(2) . ?
S003 C009 1.732(2) . ?
C005 C00A 1.531(3) . ?
C005 C00B 1.539(3) . ?
C006 C009 1.373(3) . ?
C006 C00C 1.430(3) . ?
C006 C008 1.504(3) . ?
C007 C00D 1.528(3) . ?
C007 C00A 1.531(3) . ?
C008 C00B 1.543(3) . ?
C00C C00E 1.353(3) . ?

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
O004 S002 C009 107.86(11) . . ?
O004 S002 C00D 104.96(11) . . ?
C009 S002 C00D 96.87(11) . . ?
C00E S003 C009 89.68(12) . . ?
C00A C005 C00B 116.6(2) . . ?
C009 C006 C00C 110.9(2) . . ?
C009 C006 C008 126.2(2) . . ?
C00C C006 C008 122.9(2) . . ?
C00D C007 C00A 115.9(2) . . ?
C006 C008 C00B 114.7(2) . . ?
C006 C009 S003 113.39(19) . . ?
C006 C009 S002 125.6(2) . . ?
S003 C009 S002 120.36(14) . . ?
C007 C00A C005 116.7(2) . . ?
C005 C00B C008 115.9(2) . . ?
C00E C00C C006 112.4(2) . . ?
C007 C00D S002 117.31(17) . . ?
C00C C00E S003 113.66(18) . . ?
C00C C00E Br01 126.85(18) . . ?
S003 C00E Br01 119.43(14) . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.076

