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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20201104_yamada_no3_-50__sq
_database_code_depnum_ccdc_archive 'CCDC 2212208'
loop_
_audit_author_name
_audit_author_address
'Hiroshi Katagiri'
;Yamagata University
Japan
;
_audit_update_record             
;
2022-11-17 deposited with the CCDC.	2023-01-30 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         'C36 H36 Br4 O4 S4, 0.63[C7H14]'
_chemical_formula_sum            'C40.41 H44.82 Br4 O4 S4'
_chemical_formula_weight         1042.38

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      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'

_cell_length_a                   31.1921(6)
_cell_length_b                   31.1921(6)
_cell_length_c                   24.1196(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     20323.1(9)
_cell_formula_units_Z            18
_cell_measurement_temperature    223
_cell_measurement_reflns_used    28801
_cell_measurement_theta_min      2.1840
_cell_measurement_theta_max      26.1960

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             9419
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    3.786
_shelx_estimated_absorpt_T_min   0.313
_shelx_estimated_absorpt_T_max   0.313
_exptl_absorpt_correction_T_min  0.42401
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.755
_oxdiff_exptl_absorpt_empirical_full_max 1.588
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_diffrn_ambient_temperature      223
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            84595
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.847
_diffrn_reflns_theta_max         26.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4691
_reflns_number_gt                3425
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'SHELXT2014 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL2018 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2020)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+62.5902P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4691
_refine_ls_number_parameters     249
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.023
_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
Br1 Br 0.07264(2) 0.28541(2) 0.79942(2) 0.07762(16) Uani 1 1 d . . . . .
Br2 Br 0.36966(2) 0.52690(2) 0.52799(2) 0.08037(16) Uani 1 1 d . . . . .
S1 S 0.05503(4) 0.333333 0.583333 0.0582(3) Uani 1 2 d S T P . .
S2 S 0.23376(3) 0.43957(4) 0.69589(4) 0.0599(3) Uani 1 1 d . . . . .
S3 S 0.30713(4) 0.333333 0.583333 0.0628(4) Uani 1 2 d S T P . .
C1 C 0.10114(12) 0.32519(13) 0.73551(14) 0.0520(8) Uani 1 1 d . . . . .
C2 C 0.07335(12) 0.31545(12) 0.68790(14) 0.0507(8) Uani 1 1 d . . . . .
H2 H 0.040204 0.289707 0.687296 0.061 Uiso 1 1 calc R U . . .
C3 C 0.09459(11) 0.34386(12) 0.64088(13) 0.0460(8) Uani 1 1 d . . . . .
C4 C 0.14412(11) 0.38161(11) 0.64118(13) 0.0429(7) Uani 1 1 d . . . . .
C5 C 0.17181(11) 0.39017(12) 0.68969(13) 0.0467(8) Uani 1 1 d . . . . .
C6 C 0.15012(12) 0.36237(13) 0.73695(14) 0.0518(8) Uani 1 1 d . . . . .
H6 H 0.168617 0.368781 0.769759 0.062 Uiso 1 1 calc R U . . .
O1 O 0.16557(8) 0.40849(8) 0.59429(9) 0.0517(6) Uani 1 1 d . . . . .
C7 C 0.16357(16) 0.45331(15) 0.58905(18) 0.0731(11) Uani 1 1 d . . . . .
H7 H 0.180354 0.475324 0.620478 0.088 Uiso 1 1 calc R U . . .
H7A H 0.129092 0.445824 0.588395 0.088 Uiso 1 1 calc R U . . .
C8 C 0.18951(19) 0.47810(18) 0.5347(2) 0.0936(14) Uani 1 1 d . . . . .
H8 H 0.223912 0.485395 0.536053 0.112 Uiso 1 1 calc R U . . .
H8A H 0.173059 0.455173 0.503878 0.112 Uiso 1 1 calc R U . . .
C9 C 0.1888(3) 0.5241(2) 0.5246(3) 0.145(2) Uani 1 1 d . . . . .
H9 H 0.155178 0.517946 0.528336 0.217 Uiso 1 1 calc R U . . .
H9A H 0.200706 0.535922 0.487414 0.217 Uiso 1 1 calc R U . . .
H9B H 0.209938 0.548974 0.551344 0.217 Uiso 1 1 calc R U . . .
C10 C 0.32913(12) 0.47031(14) 0.57175(14) 0.0544(9) Uani 1 1 d . . . . .
C11 C 0.32999(12) 0.42738(14) 0.56331(14) 0.0560(9) Uani 1 1 d . . . . .
H11 H 0.351825 0.426586 0.537017 0.067 Uiso 1 1 calc R U . . .
C12 C 0.29886(11) 0.38489(13) 0.59328(14) 0.0505(8) Uani 1 1 d . . . . .
C13 C 0.26687(10) 0.38636(12) 0.63338(13) 0.0461(8) Uani 1 1 d . . . . .
C14 C 0.26643(11) 0.43069(12) 0.64139(13) 0.0477(8) Uani 1 1 d . . . . .
C15 C 0.29744(11) 0.47247(13) 0.61020(14) 0.0522(8) Uani 1 1 d . . . . .
H15 H 0.296822 0.502035 0.615303 0.063 Uiso 1 1 calc R U . . .
O2 O 0.23546(8) 0.34512(9) 0.66277(9) 0.0522(5) Uani 1 1 d D . . . .
C16A C 0.2528(3) 0.3292(4) 0.7102(3) 0.065(3) Uani 0.635(13) 1 d D . P A 1
H16A H 0.275411 0.358216 0.732119 0.079 Uiso 0.635(13) 1 calc R U P A 1
H16B H 0.271321 0.313458 0.696890 0.079 Uiso 0.635(13) 1 calc R U P A 1
C17A C 0.2109(3) 0.2932(3) 0.7467(3) 0.076(3) Uani 0.635(13) 1 d D . P A 1
H17A H 0.224327 0.280184 0.774538 0.091 Uiso 0.635(13) 1 calc R U P A 1
H17B H 0.197356 0.311255 0.766428 0.091 Uiso 0.635(13) 1 calc R U P A 1
C18A C 0.1694(4) 0.2503(5) 0.7164(6) 0.089(4) Uani 0.635(13) 1 d D . P A 1
H18A H 0.158589 0.262636 0.685641 0.134 Uiso 0.635(13) 1 calc R U P A 1
H18B H 0.141936 0.231939 0.741571 0.134 Uiso 0.635(13) 1 calc R U P A 1
H18C H 0.180953 0.228690 0.702362 0.134 Uiso 0.635(13) 1 calc R U P A 1
C16B C 0.2566(6) 0.3482(4) 0.7173(4) 0.070(5) Uani 0.365(13) 1 d D . P A 2
H16C H 0.245335 0.364074 0.744058 0.085 Uiso 0.365(13) 1 calc R U P A 2
H16D H 0.292894 0.366556 0.715990 0.085 Uiso 0.365(13) 1 calc R U P A 2
C17B C 0.2373(5) 0.2946(4) 0.7319(7) 0.094(5) Uani 0.365(13) 1 d D . P A 2
H17C H 0.250778 0.280576 0.705448 0.113 Uiso 0.365(13) 1 calc R U P A 2
H17D H 0.249611 0.292974 0.768811 0.113 Uiso 0.365(13) 1 calc R U P A 2
C18B C 0.1817(6) 0.2630(6) 0.7320(13) 0.109(9) Uani 0.365(13) 1 d D . P A 2
H18D H 0.167875 0.275726 0.759069 0.163 Uiso 0.365(13) 1 calc R U P A 2
H18E H 0.172286 0.229183 0.741344 0.163 Uiso 0.365(13) 1 calc R U P A 2
H18F H 0.169003 0.263748 0.695443 0.163 Uiso 0.365(13) 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
Br1 C1 1.898(4) . ?
Br2 C10 1.896(4) . ?
S1 C3 1.775(3) . ?
S1 C3 1.775(3) 16 ?
S2 C14 1.768(3) . ?
S2 C5 1.776(3) . ?
S3 C12 1.768(3) 16 ?
S3 C12 1.768(3) . ?
C1 C2 1.378(5) . ?
C1 C6 1.381(5) . ?
C2 C3 1.387(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.398(4) . ?
C4 O1 1.367(4) . ?
C4 C5 1.398(4) . ?
C5 C6 1.387(5) . ?
C6 H6 0.9400 . ?
O1 C7 1.436(4) . ?
C7 C8 1.531(6) . ?
C7 H7 0.9800 . ?
C7 H7A 0.9800 . ?
C8 C9 1.468(7) . ?
C8 H8 0.9800 . ?
C8 H8A 0.9800 . ?
C9 H9 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.368(5) . ?
C10 C15 1.382(5) . ?
C11 C12 1.391(5) . ?
C11 H11 0.9400 . ?
C12 C13 1.407(4) . ?
C13 O2 1.363(4) . ?
C13 C14 1.403(5) . ?
C14 C15 1.393(5) . ?
C15 H15 0.9400 . ?
O2 C16B 1.454(5) . ?
O2 C16A 1.454(5) . ?
C16A C17A 1.508(7) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C17A C18A 1.508(7) . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18A H18C 0.9700 . ?
C16B C17B 1.508(7) . ?
C16B H16C 0.9800 . ?
C16B H16D 0.9800 . ?
C17B C18B 1.508(7) . ?
C17B H17C 0.9800 . ?
C17B H17D 0.9800 . ?
C18B H18D 0.9700 . ?
C18B H18E 0.9700 . ?
C18B H18F 0.9700 . ?

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
C3 S1 C3 105.88(19) . 16 ?
C14 S2 C5 105.29(14) . . ?
C12 S3 C12 106.1(2) 16 . ?
C2 C1 C6 121.1(3) . . ?
C2 C1 Br1 119.7(3) . . ?
C6 C1 Br1 119.2(3) . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 S1 117.1(2) . . ?
C4 C3 S1 122.2(3) . . ?
O1 C4 C3 120.5(3) . . ?
O1 C4 C5 120.6(3) . . ?
C3 C4 C5 118.8(3) . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 S2 116.9(2) . . ?
C4 C5 S2 122.4(3) . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C4 O1 C7 115.1(2) . . ?
O1 C7 C8 107.3(3) . . ?
O1 C7 H7 110.2 . . ?
C8 C7 H7 110.2 . . ?
O1 C7 H7A 110.2 . . ?
C8 C7 H7A 110.2 . . ?
H7 C7 H7A 108.5 . . ?
C9 C8 C7 111.9(5) . . ?
C9 C8 H8 109.2 . . ?
C7 C8 H8 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
H8 C8 H8A 107.9 . . ?
C8 C9 H9 109.5 . . ?
C8 C9 H9A 109.5 . . ?
H9 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C11 C10 C15 120.8(3) . . ?
C11 C10 Br2 119.9(3) . . ?
C15 C10 Br2 119.2(3) . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 S3 116.5(2) . . ?
C13 C12 S3 123.5(3) . . ?
O2 C13 C14 120.1(3) . . ?
O2 C13 C12 120.9(3) . . ?
C14 C13 C12 118.9(3) . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 S2 116.1(3) . . ?
C13 C14 S2 123.2(3) . . ?
C10 C15 C14 119.7(3) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C13 O2 C16B 108.7(5) . . ?
C13 O2 C16A 121.2(4) . . ?
O2 C16A C17A 112.5(6) . . ?
O2 C16A H16A 109.1 . . ?
C17A C16A H16A 109.1 . . ?
O2 C16A H16B 109.1 . . ?
C17A C16A H16B 109.1 . . ?
H16A C16A H16B 107.8 . . ?
C18A C17A C16A 114.6(8) . . ?
C18A C17A H17A 108.6 . . ?
C16A C17A H17A 108.6 . . ?
C18A C17A H17B 108.6 . . ?
C16A C17A H17B 108.6 . . ?
H17A C17A H17B 107.6 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
O2 C16B C17B 102.8(8) . . ?
O2 C16B H16C 111.2 . . ?
C17B C16B H16C 111.2 . . ?
O2 C16B H16D 111.2 . . ?
C17B C16B H16D 111.2 . . ?
H16C C16B H16D 109.1 . . ?
C18B C17B C16B 114.6(8) . . ?
C18B C17B H17C 108.6 . . ?
C16B C17B H17C 108.6 . . ?
C18B C17B H17D 108.6 . . ?
C16B C17B H17D 108.6 . . ?
H17C C17B H17D 107.6 . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.0(5) . . . . ?
Br1 C1 C2 C3 -178.6(2) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C1 C2 C3 S1 -173.9(2) . . . . ?
C3 S1 C3 C2 -127.5(3) 16 . . . ?
C3 S1 C3 C4 57.5(2) 16 . . . ?
C2 C3 C4 O1 177.7(3) . . . . ?
S1 C3 C4 O1 -7.5(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
S1 C3 C4 C5 174.8(2) . . . . ?
O1 C4 C5 C6 -179.1(3) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
O1 C4 C5 S2 6.3(4) . . . . ?
C3 C4 C5 S2 -176.0(2) . . . . ?
C14 S2 C5 C6 128.3(3) . . . . ?
C14 S2 C5 C4 -56.9(3) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
Br1 C1 C6 C5 177.2(2) . . . . ?
C4 C5 C6 C1 1.6(5) . . . . ?
S2 C5 C6 C1 176.5(2) . . . . ?
C3 C4 O1 C7 92.7(4) . . . . ?
C5 C4 O1 C7 -89.7(4) . . . . ?
C4 O1 C7 C8 179.7(3) . . . . ?
O1 C7 C8 C9 178.9(5) . . . . ?
C15 C10 C11 C12 0.1(5) . . . . ?
Br2 C10 C11 C12 -177.1(2) . . . . ?
C10 C11 C12 C13 -1.2(5) . . . . ?
C10 C11 C12 S3 -174.5(3) . . . . ?
C12 S3 C12 C11 -133.2(3) 16 . . . ?
C12 S3 C12 C13 53.8(2) 16 . . . ?
C11 C12 C13 O2 179.0(3) . . . . ?
S3 C12 C13 O2 -8.2(4) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
S3 C12 C13 C14 174.1(2) . . . . ?
O2 C13 C14 C15 -178.1(3) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
O2 C13 C14 S2 10.2(4) . . . . ?
C12 C13 C14 S2 -172.0(2) . . . . ?
C5 S2 C14 C15 133.5(2) . . . . ?
C5 S2 C14 C13 -54.5(3) . . . . ?
C11 C10 C15 C14 0.9(5) . . . . ?
Br2 C10 C15 C14 178.1(2) . . . . ?
C13 C14 C15 C10 -0.8(5) . . . . ?
S2 C14 C15 C10 171.5(2) . . . . ?
C14 C13 O2 C16B -81.4(8) . . . . ?
C12 C13 O2 C16B 100.9(8) . . . . ?
C14 C13 O2 C16A -102.3(6) . . . . ?
C12 C13 O2 C16A 80.0(6) . . . . ?
C13 O2 C16A C17A 162.6(6) . . . . ?
O2 C16A C17A C18A 50.2(16) . . . . ?
C13 O2 C16B C17B -149.7(9) . . . . ?
O2 C16B C17B C18B -58(2) . . . . ?

_refine_diff_density_max         0.630
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.056




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methylcyclohexane and chloroform (= 1:1 v/v)'
####################################################################### 
# 
# 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_sx19083
_database_code_depnum_ccdc_archive 'CCDC 2212209'
loop_
_audit_author_name
_audit_author_address
'Hiroshi Katagiri'
;Yamagata University
Japan
;
_audit_update_record             
;
2022-10-11 deposited with the CCDC.	2023-01-30 downloaded from the CCDC.
;
_audit_creation_date             2020-06-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H36 Br4 O4 S4, C6 H6'
_chemical_formula_sum            'C42 H42 Br4 O4 S4'
_chemical_formula_weight         1058.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O Br S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   31.1234(3)
_cell_length_b                   31.1234(3)
_cell_length_c                   24.1605(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     20268.0(4)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    11899
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      76.7030
_cell_measurement_theta_min      2.4640
_shelx_estimated_absorpt_T_max   0.209
_shelx_estimated_absorpt_T_min   0.190
_exptl_absorpt_coefficient_mu    6.403
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             9540
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.389
_exptl_crystal_size_min          0.356
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            22078
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.258
_diffrn_reflns_theta_min         2.840
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  15.00   0.50    0.47    --  -42.80  79.00 145.00  140
  2  ω     -4.00  36.00   0.50    0.47    --  -42.80  19.00  30.00   80
  3  ω    -37.00   0.00   0.50    0.47    --   42.80 -19.00  30.00   74
  4  ω     46.00  72.00   0.50    1.88    --  111.75 -61.00 150.00   52
  5  ω     41.00 103.00   0.50    1.88    --  111.75-125.00 150.00  124
  6  ω     45.00  72.00   0.50    1.88    --  111.75 -61.00  30.00   54
  7  ω     38.00  63.00   0.50    1.88    --  111.75 -61.00 -30.00   50
  8  ω     44.00  70.00   0.50    1.88    --  111.75 -61.00 -60.00   52
  9  ω     49.00  75.00   0.50    1.88    --  111.75 -61.00 -90.00   52
 10  ω     48.00 107.00   0.50    1.88    --  111.75-131.00 -78.00  118
 11  ω    118.00 169.00   0.50    1.88    --  111.75  77.00  60.00  102
 12  ω    140.00 172.00   0.50    1.88    --  111.75  93.00 159.00   64
 13  ω    108.00 137.00   0.50    1.88    --  111.75  93.00 159.00   58
 14  ω    -60.00 -35.00   0.50    1.88    --  -90.25  93.00 159.00   50
 15  ω    -49.00 -15.00   0.50    1.88    --  -90.25  45.00-120.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-DW'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0469138000
_diffrn_orient_matrix_UB_12      -0.0417585000
_diffrn_orient_matrix_UB_13      -0.0277780000
_diffrn_orient_matrix_UB_21      -0.0095129000
_diffrn_orient_matrix_UB_22      0.0389909000
_diffrn_orient_matrix_UB_23      -0.0278127000
_diffrn_orient_matrix_UB_31      0.0312514000
_diffrn_orient_matrix_UB_32      0.0014855000
_diffrn_orient_matrix_UB_33      -0.0502131000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4158
_reflns_number_total             4687
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.035
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4687
_refine_ls_number_restraints     245
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0817P)²+77.7230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.1584
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C16-C17 \\sim C16-C7A
 with sigma of 0.02
 C18-C17 \\sim C18-C7A
 with sigma of 0.02
 C30-C25 \\sim C25-C26 \\sim C27-C26 \\sim C27-C28 \\sim C28-C29 \\sim C29-C30
 with sigma of 0.02
 C28-C30 \\sim C29-C25 \\sim C30-C26 \\sim C25-C27 \\sim C29-C27
 with sigma of 0.02
 C19-C20 \\sim C20-C21 \\sim C21-C22 \\sim C23-C22 \\sim C23-C24 \\sim C24-C19
 with sigma of 0.02
 C19-C21 \\sim C20-C22 \\sim C21-C23 \\sim C22-C24 \\sim C24-C20 \\sim C19-C21
 with sigma of 0.02
3. Restrained planarity
 C26, C30, C28, C25, C27, C29
 with sigma of 0.1
 C22, C24, C20, C23
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C25 \\sim C26 \\sim C27 \\sim C30 \\sim C28 \\sim C29: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
C21 \\sim C20 \\sim C19 \\sim C24 \\sim C23 \\sim C22: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
C16 \\sim C17 \\sim C7A \\sim C18: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C30, C26, C25, C27, C28, C29
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C23, C24, C19, C20, C21, C22
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C16, C17, C7A, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H16C)=Sof(H16D)=Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(C7A)=Sof(H7AA)=
 Sof(H7AB)=1-FVAR(1)
 Sof(H16A)=Sof(H16B)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C17)=Sof(H17A)=
 Sof(H17B)=FVAR(1)
 Fixed Sof: C26(0.16667) H26(0.16667) C25(0.16667) H25(0.16667) C30(0.16667)
 H30(0.16667) C29(0.16667) H29(0.16667) C28(0.16667) H28(0.16667) C27(0.16667)
 H27(0.16667) C22(0.33333) H22(0.33333) C21(0.33333) H21(0.33333) C20(0.33333)
 H20(0.33333) C19(0.33333) H19(0.33333) C24(0.33333) H24(0.33333) C23(0.33333)
 H23(0.33333)
7.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C16(H16A,H16B), C16(H16C,H16D), C8(H8A,H8B), C17(H17A,H17B),
 C7A(H7AA,H7AB)
7.b Me refined with riding coordinates:
 C18(H18A,H18B,H18C), C18(H18D,H18E,H18F)
7.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11), C6(H6), C15(H15), C26(H26), C25(H25), C30(H30), C29(H29),
 C28(H28), C27(H27), C22(H22), C21(H21), C20(H20), C19(H19), C24(H24), C23(H23)
7.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.54711(2) 0.59341(2) 0.46577(2) 0.0794(2) Uani 1 1 d . . . . .
Br2 Br 0.49029(2) 0.29693(2) 0.19293(2) 0.0834(2) Uani 1 1 d . . . . .
S1 S 0.61210(4) 0.61210(4) 0.250000 0.0589(4) Uani 1 2 d S T P . .
S2 S 0.54050(4) 0.43283(3) 0.36099(4) 0.0610(3) Uani 1 1 d . . . . .
S3 S 0.36023(4) 0.36023(4) 0.250000 0.0669(4) Uani 1 2 d S T P . .
O1 O 0.57732(10) 0.50165(9) 0.26028(11) 0.0536(6) Uani 1 1 d . . . . .
O2 O 0.44397(10) 0.43132(9) 0.32911(11) 0.0549(6) Uani 1 1 d . . . . .
C4 C 0.57175(12) 0.52261(12) 0.30708(14) 0.0452(7) Uani 1 1 d . . . . .
C13 C 0.45392(13) 0.40009(11) 0.29932(15) 0.0481(8) Uani 1 1 d . . . . .
C3 C 0.58306(12) 0.57213(12) 0.30713(15) 0.0473(8) Uani 1 1 d . . . . .
C5 C 0.55301(13) 0.49489(12) 0.35543(15) 0.0482(8) Uani 1 1 d . . . . .
C2 C 0.57625(13) 0.59331(13) 0.35462(16) 0.0513(8) Uani 1 1 d . . . . .
H2 H 0.583921 0.626608 0.354527 0.062 Uiso 1 1 calc R U . . .
C14 C 0.42011(13) 0.36834(12) 0.25920(16) 0.0536(9) Uani 1 1 d . . . . .
C12 C 0.49835(14) 0.40023(12) 0.30667(15) 0.0513(8) Uani 1 1 d . . . . .
C11 C 0.50903(15) 0.36936(13) 0.27534(17) 0.0555(9) Uani 1 1 d . . . . .
H11 H 0.539276 0.369934 0.280237 0.067 Uiso 1 1 calc R U . . .
C1 C 0.55826(14) 0.56514(14) 0.40144(16) 0.0534(8) Uani 1 1 d . . . . .
C6 C 0.54674(13) 0.51623(13) 0.40289(15) 0.0520(8) Uani 1 1 d . . . . .
H6 H 0.534790 0.497602 0.435605 0.062 Uiso 1 1 calc R U . . .
C10 C 0.47512(17) 0.33790(14) 0.23704(17) 0.0590(9) Uani 1 1 d . . . . .
C15 C 0.43097(16) 0.33713(14) 0.22872(17) 0.0603(10) Uani 1 1 d . . . . .
H15 H 0.408181 0.315473 0.202401 0.072 Uiso 1 1 calc R U . . .
C7 C 0.62421(19) 0.5035(2) 0.2548(2) 0.0807(14) Uani 1 1 d . . . . .
H7A H 0.629110 0.485861 0.285603 0.097 Uiso 1 1 calc R U . . .
H7B H 0.651425 0.537965 0.255015 0.097 Uiso 1 1 calc R U . . .
C16 C 0.4165(3) 0.4129(2) 0.3792(2) 0.106(2) Uani 1 1 d D U . . .
H16A H 0.430142 0.395857 0.400854 0.127 Uiso 0.54(3) 1 calc R U P A 1
H16B H 0.381834 0.388961 0.370587 0.127 Uiso 0.54(3) 1 calc R U P A 1
H16C H 0.438418 0.411284 0.407251 0.127 Uiso 0.46(3) 1 calc R U P A 2
H16D H 0.389489 0.378983 0.372684 0.127 Uiso 0.46(3) 1 calc R U P A 2
C8 C 0.6231(3) 0.4784(3) 0.1994(3) 0.109(2) Uani 1 1 d . . . . .
H8A H 0.596598 0.443646 0.200691 0.131 Uiso 1 1 calc R U . . .
H8B H 0.615274 0.494759 0.169589 0.131 Uiso 1 1 calc R U . . .
C9 C 0.6702(4) 0.4806(4) 0.1870(5) 0.166(4) Uani 1 1 d . . . . .
H9A H 0.672638 0.476759 0.147459 0.249 Uiso 1 1 calc R U . . .
H9B H 0.671754 0.454157 0.206472 0.249 Uiso 1 1 calc R U . . .
H9C H 0.697554 0.512393 0.198785 0.249 Uiso 1 1 calc R U . . .
C18 C 0.4155(3) 0.4948(3) 0.3870(3) 0.119(2) Uani 1 1 d D U . . .
H18A H 0.417787 0.518853 0.414086 0.179 Uiso 0.54(3) 1 calc R U P A 1
H18B H 0.442211 0.511016 0.360337 0.179 Uiso 0.54(3) 1 calc R U P A 1
H18C H 0.383850 0.480846 0.367930 0.179 Uiso 0.54(3) 1 calc R U P A 1
H18D H 0.396508 0.507313 0.405991 0.179 Uiso 0.46(3) 1 calc R U P A 2
H18E H 0.449988 0.513872 0.398066 0.179 Uiso 0.46(3) 1 calc R U P A 2
H18F H 0.412919 0.497851 0.347295 0.179 Uiso 0.46(3) 1 calc R U P A 2
C17 C 0.4192(7) 0.4565(5) 0.4139(4) 0.086(3) Uani 0.54(3) 1 d D U P A 1
H17A H 0.392702 0.442008 0.441640 0.104 Uiso 0.54(3) 1 calc R U P A 1
H17B H 0.450732 0.472008 0.434090 0.104 Uiso 0.54(3) 1 calc R U P A 1
C7A C 0.3955(8) 0.4416(7) 0.4016(9) 0.109(5) Uani 0.46(3) 1 d D U P A 2
H7AA H 0.397020 0.439951 0.441986 0.131 Uiso 0.46(3) 1 calc R U P A 2
H7AB H 0.360227 0.424049 0.391593 0.131 Uiso 0.46(3) 1 calc R U P A 2
C26 C 0.624(3) 0.353(4) 0.567(4) 0.19(2) Uani 0.1667 1 d D U P B -1
H26 H 0.602928 0.363764 0.553823 0.230 Uiso 0.1667 1 calc R U P B -1
C25 C 0.606(3) 0.302(4) 0.576(5) 0.19(2) Uani 0.1667 1 d D U P B -1
H25 H 0.573101 0.278670 0.568093 0.224 Uiso 0.1667 1 calc R U P B -1
C30 C 0.638(3) 0.286(3) 0.596(6) 0.19(2) Uani 0.1667 1 d D U P B -1
H30 H 0.626388 0.252041 0.602299 0.227 Uiso 0.1667 1 calc R U P B -1
C29 C 0.689(3) 0.321(4) 0.607(4) 0.20(3) Uani 0.1667 1 d D U P B -1
H29 H 0.710213 0.310511 0.620524 0.242 Uiso 0.1667 1 calc R U P B -1
C28 C 0.706(3) 0.372(4) 0.599(5) 0.21(3) Uani 0.1667 1 d D U P B -1
H28 H 0.739387 0.395112 0.606174 0.248 Uiso 0.1667 1 calc R U P B -1
C27 C 0.674(3) 0.388(4) 0.579(5) 0.19(2) Uani 0.1667 1 d D U P B -1
H27 H 0.685978 0.421972 0.572765 0.232 Uiso 0.1667 1 calc R U P B -1
C22 C 0.5981(15) 0.2748(17) 0.3318(19) 0.205(14) Uani 0.3333 1 d D U P C -1
H22 H 0.595939 0.255414 0.300945 0.246 Uiso 0.3333 1 calc R U P C -1
C21 C 0.603(2) 0.2615(16) 0.381(2) 0.246(16) Uani 0.3333 1 d D U P C -1
H21 H 0.593421 0.228325 0.388603 0.295 Uiso 0.3333 1 calc R U P C -1
C20 C 0.621(2) 0.295(2) 0.4197(15) 0.243(15) Uani 0.3333 1 d D U P C -1
H20 H 0.635205 0.289592 0.451391 0.292 Uiso 0.3333 1 calc R U P C -1
C19 C 0.6184(18) 0.3347(18) 0.4140(17) 0.233(14) Uani 0.3333 1 d D U P C -1
H19 H 0.624926 0.356124 0.444267 0.280 Uiso 0.3333 1 calc R U P C -1
C24 C 0.6069(14) 0.3450(16) 0.367(2) 0.202(13) Uani 0.3333 1 d D U P C -1
H24 H 0.606347 0.374722 0.361840 0.243 Uiso 0.3333 1 calc R U P C -1
C23 C 0.5964(10) 0.3151(19) 0.3257(19) 0.200(13) Uani 0.3333 1 d D U P C -1
H23 H 0.587349 0.322453 0.291372 0.240 Uiso 0.3333 1 calc R U P C -1


_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
Br1 C1 1.901(4) . ?
Br2 C10 1.894(4) . ?
S1 C3 1.774(4) 4 ?
S1 C3 1.774(4) . ?
S2 C5 1.774(3) . ?
S2 C12 1.772(4) . ?
S3 C14 1.765(4) 4 ?
S3 C14 1.765(4) . ?
O1 C4 1.359(4) . ?
O1 C7 1.438(6) . ?
O2 C13 1.364(5) . ?
O2 C16 1.426(5) . ?
C4 C3 1.399(5) . ?
C4 C5 1.395(5) . ?
C13 C14 1.409(5) . ?
C13 C12 1.392(5) . ?
C3 C2 1.391(6) . ?
C5 C6 1.387(6) . ?
C2 H2 0.9400 . ?
C2 C1 1.368(6) . ?
C14 C15 1.389(6) . ?
C12 C11 1.388(6) . ?
C11 H11 0.9400 . ?
C11 C10 1.377(6) . ?
C1 C6 1.379(5) . ?
C6 H6 0.9400 . ?
C10 C15 1.377(6) . ?
C15 H15 0.9400 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 C8 1.540(9) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16D 0.9800 . ?
C16 C17 1.561(13) . ?
C16 C7A 1.450(14) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 C9 1.467(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C18 H18D 0.9700 . ?
C18 H18E 0.9700 . ?
C18 H18F 0.9700 . ?
C18 C17 1.412(13) . ?
C18 C7A 1.492(16) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C26 H26 0.9400 . ?
C26 C25 1.41(3) . ?
C26 C27 1.40(3) . ?
C25 H25 0.9400 . ?
C25 C30 1.40(3) . ?
C30 H30 0.9400 . ?
C30 C29 1.42(3) . ?
C29 H29 0.9400 . ?
C29 C28 1.40(3) . ?
C28 H28 0.9400 . ?
C28 C27 1.41(3) . ?
C27 H27 0.9400 . ?
C22 H22 0.9400 . ?
C22 C21 1.29(2) . ?
C22 C23 1.29(2) . ?
C21 H21 0.9400 . ?
C21 C20 1.29(2) . ?
C20 H20 0.9400 . ?
C20 C19 1.29(2) . ?
C19 H19 0.9400 . ?
C19 C24 1.29(2) . ?
C24 H24 0.9400 . ?
C24 C23 1.28(2) . ?
C23 H23 0.9400 . ?

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
C3 S1 C3 105.5(2) . 4 ?
C12 S2 C5 105.31(16) . . ?
C14 S3 C14 106.3(2) . 4 ?
C4 O1 C7 115.3(3) . . ?
C13 O2 C16 117.8(4) . . ?
O1 C4 C3 120.5(3) . . ?
O1 C4 C5 120.9(3) . . ?
C5 C4 C3 118.5(3) . . ?
O2 C13 C14 120.5(3) . . ?
O2 C13 C12 120.6(3) . . ?
C12 C13 C14 118.9(4) . . ?
C4 C3 S1 122.1(3) . . ?
C2 C3 S1 117.0(3) . . ?
C2 C3 C4 120.6(3) . . ?
C4 C5 S2 122.2(3) . . ?
C6 C5 S2 116.9(3) . . ?
C6 C5 C4 120.8(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.4 . . ?
C13 C14 S3 123.5(3) . . ?
C15 C14 S3 116.2(3) . . ?
C15 C14 C13 119.9(4) . . ?
C13 C12 S2 123.1(3) . . ?
C11 C12 S2 115.8(3) . . ?
C11 C12 C13 120.7(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 H11 120.2 . . ?
C2 C1 Br1 119.4(3) . . ?
C2 C1 C6 121.7(4) . . ?
C6 C1 Br1 118.9(3) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 C5 119.1(4) . . ?
C1 C6 H6 120.4 . . ?
C11 C10 Br2 119.8(3) . . ?
C11 C10 C15 120.9(4) . . ?
C15 C10 Br2 119.3(3) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 C14 120.0(4) . . ?
C10 C15 H15 120.0 . . ?
O1 C7 H7A 110.3 . . ?
O1 C7 H7B 110.3 . . ?
O1 C7 C8 107.1(5) . . ?
H7A C7 H7B 108.6 . . ?
C8 C7 H7A 110.3 . . ?
C8 C7 H7B 110.3 . . ?
O2 C16 H16A 109.6 . . ?
O2 C16 H16B 109.6 . . ?
O2 C16 H16C 108.4 . . ?
O2 C16 H16D 108.4 . . ?
O2 C16 C17 110.2(6) . . ?
O2 C16 C7A 115.7(7) . . ?
H16A C16 H16B 108.1 . . ?
H16C C16 H16D 107.4 . . ?
C17 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C7A C16 H16C 108.4 . . ?
C7A C16 H16D 108.4 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.7(7) . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H18D C18 H18E 109.5 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
C7A C18 H18D 109.5 . . ?
C7A C18 H18E 109.5 . . ?
C7A C18 H18F 109.5 . . ?
C16 C17 H17A 107.4 . . ?
C16 C17 H17B 107.4 . . ?
C18 C17 C16 119.6(8) . . ?
C18 C17 H17A 107.4 . . ?
C18 C17 H17B 107.4 . . ?
H17A C17 H17B 106.9 . . ?
C16 C7A C18 121.9(9) . . ?
C16 C7A H7AA 106.8 . . ?
C16 C7A H7AB 106.8 . . ?
C18 C7A H7AA 106.8 . . ?
C18 C7A H7AB 106.8 . . ?
H7AA C7A H7AB 106.7 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C27 C26 C25 120.4(15) . . ?
C26 C25 H25 120.1 . . ?
C30 C25 C26 119.9(11) . . ?
C30 C25 H25 120.1 . . ?
C25 C30 H30 120.0 . . ?
C25 C30 C29 119.9(13) . . ?
C29 C30 H30 120.0 . . ?
C30 C29 H29 120.1 . . ?
C28 C29 C30 119.7(11) . . ?
C28 C29 H29 120.1 . . ?
C29 C28 H28 119.7 . . ?
C29 C28 C27 120.6(15) . . ?
C27 C28 H28 119.7 . . ?
C26 C27 C28 119.5(16) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C23 C22 C21 118.9(13) . . ?
C22 C21 H21 120.5 . . ?
C22 C21 C20 118.9(16) . . ?
C20 C21 H21 120.5 . . ?
C21 C20 H20 120.6 . . ?
C21 C20 C19 118.8(15) . . ?
C19 C20 H20 120.6 . . ?
C20 C19 H19 120.3 . . ?
C24 C19 C20 119.4(18) . . ?
C24 C19 H19 120.3 . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.4(18) . . ?
C23 C24 H24 119.8 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.9(17) . . ?
C24 C23 H23 120.1 . . ?

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
Br1 C1 C6 C5 177.5(3) . . . . ?
Br2 C10 C15 C14 -177.5(3) . . . . ?
S1 C3 C2 C1 -174.0(3) . . . . ?
S2 C5 C6 C1 176.9(3) . . . . ?
S2 C12 C11 C10 171.7(3) . . . . ?
S3 C14 C15 C10 -174.2(3) . . . . ?
O1 C4 C3 S1 -8.0(4) . . . . ?
O1 C4 C3 C2 178.4(3) . . . . ?
O1 C4 C5 S2 5.7(4) . . . . ?
O1 C4 C5 C6 -179.1(3) . . . . ?
O1 C7 C8 C9 176.3(7) . . . . ?
O2 C13 C14 S3 -8.2(4) . . . . ?
O2 C13 C14 C15 179.3(3) . . . . ?
O2 C13 C12 S2 9.8(4) . . . . ?
O2 C13 C12 C11 -178.3(3) . . . . ?
O2 C16 C17 C18 41.0(16) . . . . ?
O2 C16 C7A C18 -22(3) . . . . ?
C4 O1 C7 C8 -179.5(4) . . . . ?
C4 C3 C2 C1 -0.1(5) . . . . ?
C4 C5 C6 C1 1.4(5) . . . . ?
C13 O2 C16 C17 167.1(7) . . . . ?
C13 O2 C16 C7A -164.1(13) . . . . ?
C13 C14 C15 C10 -1.2(5) . . . . ?
C13 C12 C11 C10 -0.7(5) . . . . ?
C3 S1 C3 C4 58.2(2) 4 . . . ?
C3 S1 C3 C2 -127.9(3) 4 . . . ?
C3 C4 C5 S2 -176.6(2) . . . . ?
C3 C4 C5 C6 -1.4(5) . . . . ?
C3 C2 C1 Br1 -178.2(3) . . . . ?
C3 C2 C1 C6 0.1(5) . . . . ?
C5 S2 C12 C13 -54.1(3) . . . . ?
C5 S2 C12 C11 133.6(3) . . . . ?
C5 C4 C3 S1 174.3(2) . . . . ?
C5 C4 C3 C2 0.7(5) . . . . ?
C2 C1 C6 C5 -0.8(5) . . . . ?
C14 S3 C14 C13 53.9(2) 4 . . . ?
C14 S3 C14 C15 -133.4(3) 4 . . . ?
C14 C13 C12 S2 -172.4(2) . . . . ?
C14 C13 C12 C11 -0.5(5) . . . . ?
C12 S2 C5 C4 -56.9(3) . . . . ?
C12 S2 C5 C6 127.7(3) . . . . ?
C12 C13 C14 S3 173.9(3) . . . . ?
C12 C13 C14 C15 1.4(5) . . . . ?
C12 C11 C10 Br2 178.4(3) . . . . ?
C12 C11 C10 C15 1.0(6) . . . . ?
C11 C10 C15 C14 -0.1(6) . . . . ?
C7 O1 C4 C3 93.6(4) . . . . ?
C7 O1 C4 C5 -88.8(4) . . . . ?
C16 O2 C13 C14 88.4(5) . . . . ?
C16 O2 C13 C12 -93.8(5) . . . . ?
C26 C25 C30 C29 -1(2) . . . . ?
C25 C26 C27 C28 0(2) . . . . ?
C25 C30 C29 C28 1(2) . . . . ?
C30 C29 C28 C27 0(2) . . . . ?
C29 C28 C27 C26 0(2) . . . . ?
C27 C26 C25 C30 0(2) . . . . ?
C22 C21 C20 C19 22(11) . . . . ?
C21 C22 C23 C24 11(5) . . . . ?
C21 C20 C19 C24 -13(10) . . . . ?
C20 C19 C24 C23 2(9) . . . . ?
C19 C24 C23 C22 -1(5) . . . . ?
C23 C22 C21 C20 -21(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.703
_oxdiff_exptl_absorpt_empirical_full_min 0.565
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: benzene'
####################################################################### 
# 
# 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_20200810_yamada_no4_-50__sq
_database_code_depnum_ccdc_archive 'CCDC 2212210'
loop_
_audit_author_name
_audit_author_address
'Hiroshi Katagiri'
;Yamagata University
Japan
;
_audit_update_record             
;
2022-11-17 deposited with the CCDC.	2023-01-30 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         'C36 H36 Br4 O4 S4, 1[C7H8]'
_chemical_formula_sum            'C43 H44 Br4 O4 S4'
_chemical_formula_weight         1072.66

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'
Br Br -0.2901 2.4595 '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      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'y+2/3, x+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'y+1/3, x+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-y+2/3, -x+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-y+1/3, -x+2/3, z+1/6'

_cell_length_a                   31.2941(5)
_cell_length_b                   31.2941(5)
_cell_length_c                   24.1681(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     20497.4(7)
_cell_formula_units_Z            18
_cell_measurement_temperature    223
_cell_measurement_reflns_used    26301
_cell_measurement_theta_min      1.9040
_cell_measurement_theta_max      28.6690

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_F_000             9684
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.757
_shelx_estimated_absorpt_T_min   0.520
_shelx_estimated_absorpt_T_max   0.520
_exptl_absorpt_correction_T_min  0.61328
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.823
_oxdiff_exptl_absorpt_empirical_full_max 1.383
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      223
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            92214
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.603
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5243
_reflns_number_gt                3666
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'SHELXT2014 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL2018 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2020)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0468P)²+50.5879P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5243
_refine_ls_number_parameters     274
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.041
_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 0.27825(3) 0.333333 0.083333 0.0676(3) Uani 1 2 d S T P . .
S2 S 0.09984(3) 0.22717(4) -0.02759(4) 0.0716(3) Uani 1 1 d . . . . .
S3 S 0.02661(4) 0.333333 0.083333 0.0751(4) Uani 1 2 d S T P . .
Br1 Br 0.25997(2) 0.37957(2) -0.13228(2) 0.09088(17) Uani 1 1 d . . . . .
Br2 Br -0.03657(2) 0.14095(2) 0.13899(2) 0.09320(18) Uani 1 1 d . . . . .
O1 O 0.16841(8) 0.25815(8) 0.07287(9) 0.0612(6) Uani 1 1 d D . . . .
O2 O 0.09781(8) 0.32133(9) 0.00445(9) 0.0634(6) Uani 1 1 d D . . . .
C1 C 0.18934(11) 0.28497(11) 0.02604(12) 0.0525(7) Uani 1 1 d D . . . .
C2 C 0.23868(11) 0.32257(12) 0.02622(13) 0.0547(7) Uani 1 1 d . . . . .
C3 C 0.25963(12) 0.35022(12) -0.02089(14) 0.0602(8) Uani 1 1 d . . . . .
H3 H 0.292809 0.375560 -0.020704 0.072 Uiso 1 1 calc R U . . .
C4 C 0.23165(12) 0.34049(13) -0.06815(14) 0.0621(8) Uani 1 1 d . . . . .
C5 C 0.18296(12) 0.30379(13) -0.06927(14) 0.0624(8) Uani 1 1 d . . . . .
H5 H 0.164347 0.297339 -0.101884 0.075 Uiso 1 1 calc R U . . .
C6 C 0.16158(11) 0.27639(12) -0.02186(13) 0.0563(8) Uani 1 1 d . . . . .
C7 C 0.06674(10) 0.28041(12) 0.03390(13) 0.0565(8) Uani 1 1 d D . . . .
C8 C 0.06723(11) 0.23631(13) 0.02654(13) 0.0579(8) Uani 1 1 d . . . . .
C9 C 0.03635(12) 0.19494(14) 0.05744(14) 0.0643(9) Uani 1 1 d . . . . .
H9 H 0.037023 0.165486 0.052541 0.077 Uiso 1 1 calc R U . . .
C10 C 0.00458(12) 0.19708(14) 0.09543(14) 0.0662(9) Uani 1 1 d . . . . .
C11 C 0.00358(12) 0.23994(15) 0.10374(14) 0.0674(9) Uani 1 1 d . . . . .
H11 H -0.018269 0.240807 0.129806 0.081 Uiso 1 1 calc R U . . .
C12 C 0.03461(11) 0.28185(14) 0.07387(14) 0.0617(8) Uani 1 1 d . . . . .
C13A C 0.1726(6) 0.2149(4) 0.0806(4) 0.081(3) Uani 0.722(10) 1 d D . P A 1
H13A H 0.207365 0.224188 0.084987 0.097 Uiso 0.722(10) 1 calc R U P A 1
H13B H 0.159264 0.193059 0.048427 0.097 Uiso 0.722(10) 1 calc R U P A 1
C14A C 0.1435(3) 0.1885(3) 0.1326(4) 0.095(3) Uani 0.722(10) 1 d D . P A 1
H14A H 0.155935 0.211374 0.164010 0.114 Uiso 0.722(10) 1 calc R U P A 1
H14B H 0.108705 0.178493 0.127231 0.114 Uiso 0.722(10) 1 calc R U P A 1
C15A C 0.1476(3) 0.1442(3) 0.1456(4) 0.146(4) Uani 0.722(10) 1 d D . P A 1
H15A H 0.128766 0.128435 0.178697 0.219 Uiso 0.722(10) 1 calc R U P A 1
H15B H 0.134783 0.121208 0.114865 0.219 Uiso 0.722(10) 1 calc R U P A 1
H15C H 0.181980 0.154065 0.151619 0.219 Uiso 0.722(10) 1 calc R U P A 1
C13B C 0.1642(17) 0.2091(8) 0.0700(9) 0.087(10) Uani 0.278(10) 1 d D . P A 2
H13C H 0.190948 0.210938 0.047188 0.104 Uiso 0.278(10) 1 calc R U P A 2
H13D H 0.132740 0.185578 0.052642 0.104 Uiso 0.278(10) 1 calc R U P A 2
C14B C 0.1668(8) 0.1919(7) 0.1261(8) 0.099(7) Uani 0.278(10) 1 d D . P A 2
H14C H 0.165882 0.160305 0.122688 0.119 Uiso 0.278(10) 1 calc R U P A 2
H14D H 0.198811 0.215565 0.142147 0.119 Uiso 0.278(10) 1 calc R U P A 2
C15B C 0.1283(12) 0.1855(12) 0.1652(10) 0.193(16) Uani 0.278(10) 1 d D . P A 2
H15D H 0.133794 0.174218 0.200436 0.289 Uiso 0.278(10) 1 calc R U P A 2
H15E H 0.129320 0.216755 0.170282 0.289 Uiso 0.278(10) 1 calc R U P A 2
H15F H 0.096275 0.161301 0.150754 0.289 Uiso 0.278(10) 1 calc R U P A 2
C16A C 0.0771(6) 0.3192(6) -0.0513(4) 0.084(4) Uani 0.435(19) 1 d D . P B 1
H16A H 0.040986 0.300888 -0.050230 0.100 Uiso 0.435(19) 1 calc R U P B 1
H16B H 0.088329 0.303016 -0.077620 0.100 Uiso 0.435(19) 1 calc R U P B 1
C17A C 0.0959(9) 0.3717(6) -0.0675(6) 0.125(6) Uani 0.435(19) 1 d D . P B 1
H17A H 0.082703 0.386504 -0.041790 0.151 Uiso 0.435(19) 1 calc R U P B 1
H17B H 0.083695 0.372617 -0.104607 0.151 Uiso 0.435(19) 1 calc R U P B 1
C18A C 0.1511(9) 0.4019(8) -0.0674(12) 0.144(11) Uani 0.435(19) 1 d D . P B 1
H18A H 0.161301 0.435547 -0.078149 0.216 Uiso 0.435(19) 1 calc R U P B 1
H18B H 0.163380 0.401817 -0.030575 0.216 Uiso 0.435(19) 1 calc R U P B 1
H18C H 0.164372 0.387928 -0.093404 0.216 Uiso 0.435(19) 1 calc R U P B 1
C16B C 0.0807(4) 0.3375(4) -0.0416(4) 0.081(3) Uani 0.565(19) 1 d D . P B 2
H16C H 0.063249 0.354043 -0.027785 0.097 Uiso 0.565(19) 1 calc R U P B 2
H16D H 0.057234 0.308709 -0.063100 0.097 Uiso 0.565(19) 1 calc R U P B 2
C17B C 0.1227(4) 0.3728(4) -0.0793(4) 0.090(3) Uani 0.565(19) 1 d D . P B 2
H17C H 0.136356 0.354479 -0.097970 0.108 Uiso 0.565(19) 1 calc R U P B 2
H17D H 0.109275 0.385082 -0.107819 0.108 Uiso 0.565(19) 1 calc R U P B 2
C18B C 0.1630(5) 0.4154(6) -0.0500(7) 0.101(4) Uani 0.565(19) 1 d D . P B 2
H18D H 0.188340 0.436219 -0.076373 0.151 Uiso 0.565(19) 1 calc R U P B 2
H18E H 0.150046 0.434321 -0.032184 0.151 Uiso 0.565(19) 1 calc R U P B 2
H18F H 0.177156 0.403684 -0.022325 0.151 Uiso 0.565(19) 1 calc R U P B 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
S1 C2 1.771(3) 16_554 ?
S1 C2 1.771(3) . ?
S2 C8 1.768(3) . ?
S2 C6 1.774(3) . ?
S3 C12 1.765(3) . ?
S3 C12 1.765(3) 16_554 ?
Br1 C4 1.897(3) . ?
Br2 C10 1.895(4) . ?
O1 C1 1.366(4) . ?
O1 C13A 1.437(8) . ?
O1 C13B 1.475(13) . ?
O2 C7 1.359(4) . ?
O2 C16B 1.433(9) . ?
O2 C16A 1.482(10) . ?
C1 C6 1.391(4) . ?
C1 C2 1.397(4) . ?
C2 C3 1.381(5) . ?
C3 C4 1.378(5) . ?
C3 H3 0.9400 . ?
C4 C5 1.375(5) . ?
C5 C6 1.386(5) . ?
C5 H5 0.9400 . ?
C7 C8 1.399(5) . ?
C7 C12 1.411(4) . ?
C8 C9 1.384(5) . ?
C9 C10 1.379(5) . ?
C9 H9 0.9400 . ?
C10 C11 1.372(5) . ?
C11 C12 1.382(5) . ?
C11 H11 0.9400 . ?
C13A C14A 1.530(10) . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C14A C15A 1.488(9) . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C15A H15C 0.9700 . ?
C13B C14B 1.477(16) . ?
C13B H13C 0.9800 . ?
C13B H13D 0.9800 . ?
C14B C15B 1.462(16) . ?
C14B H14C 0.9800 . ?
C14B H14D 0.9800 . ?
C15B H15D 0.9700 . ?
C15B H15E 0.9700 . ?
C15B H15F 0.9700 . ?
C16A C17A 1.496(13) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C17A C18A 1.499(15) . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C18A H18C 0.9700 . ?
C16B C17B 1.524(12) . ?
C16B H16C 0.9800 . ?
C16B H16D 0.9800 . ?
C17B C18B 1.480(13) . ?
C17B H17C 0.9800 . ?
C17B H17D 0.9800 . ?
C18B H18D 0.9700 . ?
C18B H18E 0.9700 . ?
C18B H18F 0.9700 . ?

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 C2 105.64(18) 16_554 . ?
C8 S2 C6 105.54(14) . . ?
C12 S3 C12 106.5(2) . 16_554 ?
C1 O1 C13A 116.4(4) . . ?
C1 O1 C13B 111.5(8) . . ?
C7 O2 C16B 121.5(5) . . ?
C7 O2 C16A 110.1(6) . . ?
O1 C1 C6 120.7(3) . . ?
O1 C1 C2 120.2(3) . . ?
C6 C1 C2 119.1(3) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 S1 117.1(2) . . ?
C1 C2 S1 122.4(3) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 Br1 119.2(3) . . ?
C3 C4 Br1 119.6(3) . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 S2 116.9(2) . . ?
C1 C6 S2 122.4(3) . . ?
O2 C7 C8 120.5(3) . . ?
O2 C7 C12 120.9(3) . . ?
C8 C7 C12 118.6(3) . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 S2 115.9(3) . . ?
C7 C8 S2 123.1(3) . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 Br2 119.2(3) . . ?
C9 C10 Br2 119.8(3) . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.0(3) . . ?
C11 C12 S3 116.5(3) . . ?
C7 C12 S3 123.1(3) . . ?
O1 C13A C14A 107.7(8) . . ?
O1 C13A H13A 110.2 . . ?
C14A C13A H13A 110.2 . . ?
O1 C13A H13B 110.2 . . ?
C14A C13A H13B 110.2 . . ?
H13A C13A H13B 108.5 . . ?
C15A C14A C13A 111.7(8) . . ?
C15A C14A H14A 109.3 . . ?
C13A C14A H14A 109.3 . . ?
C15A C14A H14B 109.3 . . ?
C13A C14A H14B 109.3 . . ?
H14A C14A H14B 107.9 . . ?
C14A C15A H15A 109.5 . . ?
C14A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O1 C13B C14B 110.0(14) . . ?
O1 C13B H13C 109.7 . . ?
C14B C13B H13C 109.7 . . ?
O1 C13B H13D 109.7 . . ?
C14B C13B H13D 109.7 . . ?
H13C C13B H13D 108.2 . . ?
C15B C14B C13B 116.9(18) . . ?
C15B C14B H14C 108.1 . . ?
C13B C14B H14C 108.1 . . ?
C15B C14B H14D 108.1 . . ?
C13B C14B H14D 108.1 . . ?
H14C C14B H14D 107.3 . . ?
C14B C15B H15D 109.5 . . ?
C14B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C14B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
O2 C16A C17A 105.4(9) . . ?
O2 C16A H16A 110.7 . . ?
C17A C16A H16A 110.7 . . ?
O2 C16A H16B 110.7 . . ?
C17A C16A H16B 110.7 . . ?
H16A C16A H16B 108.8 . . ?
C16A C17A C18A 112.8(13) . . ?
C16A C17A H17A 109.0 . . ?
C18A C17A H17A 109.0 . . ?
C16A C17A H17B 109.0 . . ?
C18A C17A H17B 109.0 . . ?
H17A C17A H17B 107.8 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
O2 C16B C17B 112.4(9) . . ?
O2 C16B H16C 109.1 . . ?
C17B C16B H16C 109.1 . . ?
O2 C16B H16D 109.1 . . ?
C17B C16B H16D 109.1 . . ?
H16C C16B H16D 107.8 . . ?
C18B C17B C16B 113.9(11) . . ?
C18B C17B H17C 108.8 . . ?
C16B C17B H17C 108.8 . . ?
C18B C17B H17D 108.8 . . ?
C16B C17B H17D 108.8 . . ?
H17C C17B H17D 107.7 . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13A O1 C1 C6 93.2(8) . . . . ?
C13B O1 C1 C6 79(2) . . . . ?
C13A O1 C1 C2 -88.9(8) . . . . ?
C13B O1 C1 C2 -103(2) . . . . ?
O1 C1 C2 C3 -179.0(3) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
O1 C1 C2 S1 6.9(4) . . . . ?
C6 C1 C2 S1 -175.2(2) . . . . ?
C2 S1 C2 C3 128.0(3) 16_554 . . . ?
C2 S1 C2 C1 -57.6(2) 16_554 . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
S1 C2 C3 C4 174.4(2) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C2 C3 C4 Br1 178.4(2) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
Br1 C4 C5 C6 -177.5(2) . . . . ?
C4 C5 C6 C1 -1.7(5) . . . . ?
C4 C5 C6 S2 -176.1(2) . . . . ?
O1 C1 C6 C5 179.8(3) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
O1 C1 C6 S2 -6.0(4) . . . . ?
C2 C1 C6 S2 176.1(2) . . . . ?
C8 S2 C6 C5 -128.0(3) . . . . ?
C8 S2 C6 C1 57.6(3) . . . . ?
C16B O2 C7 C8 103.8(7) . . . . ?
C16A O2 C7 C8 81.9(8) . . . . ?
C16B O2 C7 C12 -78.5(7) . . . . ?
C16A O2 C7 C12 -100.4(8) . . . . ?
O2 C7 C8 C9 178.5(3) . . . . ?
C12 C7 C8 C9 0.8(4) . . . . ?
O2 C7 C8 S2 -10.3(4) . . . . ?
C12 C7 C8 S2 172.0(2) . . . . ?
C6 S2 C8 C9 -133.9(2) . . . . ?
C6 S2 C8 C7 54.6(3) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
S2 C8 C9 C10 -171.3(2) . . . . ?
C8 C9 C10 C11 -1.0(5) . . . . ?
C8 C9 C10 Br2 -178.5(2) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
Br2 C10 C11 C12 177.6(2) . . . . ?
C10 C11 C12 C7 1.3(5) . . . . ?
C10 C11 C12 S3 174.7(3) . . . . ?
O2 C7 C12 C11 -179.4(3) . . . . ?
C8 C7 C12 C11 -1.7(4) . . . . ?
O2 C7 C12 S3 7.6(4) . . . . ?
C8 C7 C12 S3 -174.6(2) . . . . ?
C12 S3 C12 C11 133.6(3) 16_554 . . . ?
C12 S3 C12 C7 -53.2(2) 16_554 . . . ?
C1 O1 C13A C14A -175.7(7) . . . . ?
O1 C13A C14A C15A -177.4(10) . . . . ?
C1 O1 C13B C14B 150.8(19) . . . . ?
O1 C13B C14B C15B 61(4) . . . . ?
C7 O2 C16A C17A 150.0(11) . . . . ?
O2 C16A C17A C18A 58(2) . . . . ?
C7 O2 C16B C17B -161.5(8) . . . . ?
O2 C16B C17B C18B -53(2) . . . . ?

_refine_diff_density_max         0.733
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.055




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
