# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_wart_liyon2i
_audit_block_doi                 10.5517/cc7721k
_database_code_depnum_ccdc_archive 'CCDC 215327'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/om030581b 2003
_audit_update_record             
;
2003-07-14 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
;
[(Di-tert-butylphosphanyl)ethylcyclopentadienyl-P]
(hydrido)(diphenylsilyl)cobalt(III)
;
_chemical_name_common            ?
_chemical_formula_moiety         'C27 H38 Co P Si'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C27 H38 Co P Si'
_chemical_formula_weight         480.56
_chemical_melting_point          '415 K, decomp.'
_chemical_compound_source        'synthetic              '

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.996(2)
_cell_length_b                   14.546(2)
_cell_length_c                   17.271(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2511.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.9

_exptl_crystal_description       'irregular shape'
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  1.0
_exptl_absorpt_correction_T_max  1.0

_exptl_special_details           
;
IPDS measurement on 11.7.2001.
Short descriptions of the IPDS are given in (e.g.) :
Schuett W et al., J. Organomet. Chem. 443 (1993) C33-C36 and
Sheldrick G M et al., Acta Crystallogr. B51 (1995) 89-98.
Completeness of unique data set in Laue class mmm 98 %,
but Friedel pairs kept separate in the refinement.
36035 measured reflections including unobserved and forbidden ones.
3 forbidden reflections with 5<I/σ(I)<12 neglected.
;

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Stoe IPDS area detector diffractometer'
_diffrn_measurement_method       '276 exposures, Δ φ 1.3 °'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            35965
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         26.08
_diffrn_measured_fraction_theta_max 0.98
_diffrn_reflns_theta_full        ?
_diffrn_measured_fraction_theta_full ?
_reflns_number_total             4872
_reflns_number_gt                3355
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Stoe IPDS software'
_computing_cell_refinement       'Stoe IPDS software'
_computing_data_reduction        'Stoe IPDS software and SHELXL-93'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  
;
The first CIF was issued by SHELXL-93.
The edited CIF is finally treated with the program CIF2SX
written by L. Farrugia, Univ. of Glasgow (1997)
and a refinement cycle is repeated to assure that
essential parameters were not changed.
;

_refine_special_details          
;
Last refinement cycle on 4.11.2002 at 16:48.
Refinement on F² for ALL reflections except for 0 with very negative F²
or flagged by the user for potential systematic errors.  Weighted R-factors
wR and all goodnesses of fit S are based on F², conventional R-factors R
are based on F, with F set to zero for negative F². The observed criterion
of F² > 2sigma(F²) is used only for calculating  R_factor_obs etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'calc w=1/[σ²(Fo²)]'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.018(14)
_refine_ls_number_reflns         4872
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_all         0.0586
_refine_ls_wR_factor_ref         0.0564
_refine_ls_goodness_of_fit_all   1.102
_refine_ls_goodness_of_fit_ref   1.295
_refine_ls_restrained_S_all      1.102
_refine_ls_restrained_S_obs      1.295
_refine_ls_shift/su_max          -0.001
_refine_ls_shift/esd_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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Co1 Co 0.41119(3) 0.39003(3) 0.34930(3) 0.03936(11) Uani 1 d . .
H1 H 0.4073(27) 0.4168(18) 0.2761(15) 0.047(8) Uiso 1 d . .
P1 P 0.62828(6) 0.38912(6) 0.34497(5) 0.0364(2) Uani 1 d . .
Si1 Si 0.35583(7) 0.53891(5) 0.34793(5) 0.0368(2) Uani 1 d . .
H2 H 0.4562(21) 0.5980(19) 0.3182(12) 0.039(7) Uiso 1 d . .
C1 C 0.4236(3) 0.2540(2) 0.3786(2) 0.0519(9) Uani 1 d . .
C2 C 0.3825(4) 0.3052(3) 0.4433(2) 0.0716(12) Uani 1 d . .
H3 H 0.4272(4) 0.3094(3) 0.4904(2) 0.086 Uiso 1 calc R .
C3 C 0.2667(5) 0.3471(3) 0.4249(4) 0.098(2) Uani 1 d . .
H4 H 0.2189(5) 0.3856(3) 0.4578(4) 0.118 Uiso 1 calc R .
C4 C 0.2292(3) 0.3253(3) 0.3513(4) 0.094(2) Uani 1 d . .
H5 H 0.1538(3) 0.3465(3) 0.3253(4) 0.113 Uiso 1 calc R .
C5 C 0.3280(4) 0.2638(3) 0.3218(2) 0.0725(13) Uani 1 d . .
H6 H 0.3278(4) 0.2357(3) 0.2735(2) 0.087 Uiso 1 calc R .
C6 C 0.5541(3) 0.2050(2) 0.3675(3) 0.0779(14) Uani 1 d . .
H7 H 0.5627(3) 0.1572(2) 0.4063(3) 0.094 Uiso 1 calc R .
H8 H 0.5548(3) 0.1759(2) 0.3170(3) 0.094 Uiso 1 calc R .
C7 C 0.6704(3) 0.2689(2) 0.3735(2) 0.0556(10) Uani 1 d . .
H9 H 0.7420(3) 0.2466(2) 0.3407(2) 0.067 Uiso 1 calc R .
H10 H 0.7028(3) 0.2688(2) 0.4265(2) 0.067 Uiso 1 calc R .
C8 C 0.7009(3) 0.4025(3) 0.2444(2) 0.0500(9) Uani 1 d . .
C9 C 0.6416(4) 0.3251(3) 0.1959(2) 0.0747(12) Uani 1 d . .
H11 H 0.5458(4) 0.3292(3) 0.1968(2) 0.112 Uiso 1 calc R .
H12 H 0.6690(4) 0.2670(3) 0.2168(2) 0.112 Uiso 1 calc R .
H13 H 0.6727(4) 0.3304(3) 0.1435(2) 0.112 Uiso 1 calc R .
C10 C 0.8528(3) 0.3954(3) 0.2426(2) 0.0754(12) Uani 1 d . .
H14 H 0.8908(3) 0.4440(3) 0.2731(2) 0.113 Uiso 1 calc R .
H15 H 0.8835(3) 0.4006(3) 0.1901(2) 0.113 Uiso 1 calc R .
H16 H 0.8798(3) 0.3371(3) 0.2634(2) 0.113 Uiso 1 calc R .
C11 C 0.6584(4) 0.4939(3) 0.2090(2) 0.0695(12) Uani 1 d . .
H17 H 0.5626(4) 0.4987(3) 0.2101(2) 0.104 Uiso 1 calc R .
H18 H 0.6891(4) 0.4972(3) 0.1564(2) 0.104 Uiso 1 calc R .
H19 H 0.6966(4) 0.5435(3) 0.2383(2) 0.104 Uiso 1 calc R .
C12 C 0.7297(3) 0.4565(3) 0.4171(2) 0.0520(10) Uani 1 d . .
C13 C 0.6507(4) 0.4557(3) 0.4931(2) 0.0786(13) Uani 1 d . .
H20 H 0.6396(4) 0.3935(3) 0.5104(2) 0.118 Uiso 1 calc R .
H21 H 0.5645(4) 0.4831(3) 0.4849(2) 0.118 Uiso 1 calc R .
H22 H 0.6986(4) 0.4901(3) 0.5316(2) 0.118 Uiso 1 calc R .
C14 C 0.8705(3) 0.4180(3) 0.4334(3) 0.0881(15) Uani 1 d . .
H23 H 0.8635(3) 0.3548(3) 0.4489(3) 0.132 Uiso 1 calc R .
H24 H 0.9116(3) 0.4529(3) 0.4742(3) 0.132 Uiso 1 calc R .
H25 H 0.9240(3) 0.4223(3) 0.3874(3) 0.132 Uiso 1 calc R .
C15 C 0.7441(4) 0.5569(3) 0.3927(2) 0.0689(12) Uani 1 d . .
H26 H 0.7933(4) 0.5602(3) 0.3451(2) 0.103 Uiso 1 calc R .
H27 H 0.7910(4) 0.5902(3) 0.4322(2) 0.103 Uiso 1 calc R .
H28 H 0.6569(4) 0.5833(3) 0.3855(2) 0.103 Uiso 1 calc R .
C16 C 0.2077(3) 0.5678(2) 0.2834(2) 0.0381(8) Uani 1 d . .
C17 C 0.1974(3) 0.5306(3) 0.2093(2) 0.0549(10) Uani 1 d . .
H29 H 0.2591(3) 0.4865(3) 0.1937(2) 0.066 Uiso 1 calc R .
C18 C 0.0977(3) 0.5574(2) 0.1581(2) 0.0610(9) Uani 1 d . .
H30 H 0.0946(3) 0.5320(2) 0.1087(2) 0.073 Uiso 1 calc R .
C19 C 0.0043(3) 0.6206(3) 0.1798(2) 0.0584(9) Uani 1 d . .
H31 H -0.0628(3) 0.6386(3) 0.1456(2) 0.070 Uiso 1 calc R .
C20 C 0.0107(3) 0.6573(2) 0.2526(2) 0.0532(9) Uani 1 d . .
H32 H -0.0529(3) 0.7001(2) 0.2681(2) 0.064 Uiso 1 calc R .
C21 C 0.1097(3) 0.6317(2) 0.3028(2) 0.0451(8) Uani 1 d . .
H33 H 0.1115(3) 0.6580(2) 0.3519(2) 0.054 Uiso 1 calc R .
C22 C 0.3158(3) 0.5962(3) 0.4443(2) 0.0453(8) Uani 1 d . .
C23 C 0.4022(4) 0.6594(3) 0.4776(2) 0.0650(10) Uani 1 d . .
H34 H 0.4819(4) 0.6728(3) 0.4522(2) 0.078 Uiso 1 calc R .
C24 C 0.3758(5) 0.7026(3) 0.5458(3) 0.091(2) Uani 1 d . .
H35 H 0.4361(5) 0.7450(3) 0.5659(3) 0.110 Uiso 1 calc R .
C25 C 0.2610(7) 0.6834(4) 0.5841(3) 0.101(2) Uani 1 d . .
H36 H 0.2431(7) 0.7123(4) 0.6310(3) 0.121 Uiso 1 calc R .
C26 C 0.1702(5) 0.6215(4) 0.5544(2) 0.0875(14) Uani 1 d . .
H37 H 0.0908(5) 0.6087(4) 0.5803(2) 0.105 Uiso 1 calc R .
C27 C 0.2000(4) 0.5792(3) 0.4855(2) 0.0629(12) Uani 1 d . .
H38 H 0.1392(4) 0.5370(3) 0.4656(2) 0.076 Uiso 1 calc R .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 C3 2.045(4) . ?
Co1 C1 2.047(3) . ?
Co1 C4 2.048(3) . ?
Co1 C2 2.060(4) . ?
Co1 C5 2.070(4) . ?
Co1 P1 2.1714(8) . ?
Co1 Si1 2.2352(9) . ?
P1 C7 1.865(3) . ?
P1 C12 1.881(3) . ?
P1 C8 1.892(3) . ?
Si1 C16 1.901(3) . ?
Si1 C22 1.904(3) . ?
C1 C5 1.376(5) . ?
C1 C2 1.406(5) . ?
C1 C6 1.498(4) . ?
C2 C3 1.346(6) . ?
C3 C4 1.362(7) . ?
C4 C5 1.426(6) . ?
C6 C7 1.492(4) . ?
C8 C10 1.522(4) . ?
C8 C9 1.523(5) . ?
C8 C11 1.524(5) . ?
C12 C15 1.526(4) . ?
C12 C13 1.533(5) . ?
C12 C14 1.541(5) . ?
C16 C21 1.391(4) . ?
C16 C17 1.393(4) . ?
C17 C18 1.388(4) . ?
C18 C19 1.363(5) . ?
C19 C20 1.367(5) . ?
C20 C21 1.367(4) . ?
C22 C27 1.381(4) . ?
C22 C23 1.386(5) . ?
C23 C24 1.361(5) . ?
C24 C25 1.354(7) . ?
C25 C26 1.378(7) . ?
C26 C27 1.371(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
C3 Co1 C1 65.8(2) . . ?
C3 Co1 C4 38.9(2) . . ?
C1 Co1 C4 66.74(15) . . ?
C3 Co1 C2 38.3(2) . . ?
C1 Co1 C2 40.03(13) . . ?
C4 Co1 C2 65.6(2) . . ?
C3 Co1 C5 65.9(2) . . ?
C1 Co1 C5 39.04(13) . . ?
C4 Co1 C5 40.5(2) . . ?
C2 Co1 C5 66.0(2) . . ?
C3 Co1 P1 136.6(2) . . ?
C1 Co1 P1 86.69(9) . . ?
C4 Co1 P1 152.28(13) . . ?
C2 Co1 P1 99.37(13) . . ?
C5 Co1 P1 112.84(12) . . ?
C3 Co1 Si1 97.34(13) . . ?
C1 Co1 Si1 162.65(10) . . ?
C4 Co1 Si1 103.03(13) . . ?
C2 Co1 Si1 123.65(13) . . ?
C5 Co1 Si1 139.22(13) . . ?
P1 Co1 Si1 104.65(3) . . ?
C7 P1 C12 101.1(2) . . ?
C7 P1 C8 104.6(2) . . ?
C12 P1 C8 110.3(2) . . ?
C7 P1 Co1 102.83(10) . . ?
C12 P1 Co1 120.84(11) . . ?
C8 P1 Co1 114.47(10) . . ?
C16 Si1 C22 104.58(13) . . ?
C16 Si1 Co1 114.43(10) . . ?
C22 Si1 Co1 117.85(12) . . ?
C5 C1 C2 108.0(3) . . ?
C5 C1 C6 124.3(4) . . ?
C2 C1 C6 127.4(4) . . ?
C5 C1 Co1 71.4(2) . . ?
C2 C1 Co1 70.5(2) . . ?
C6 C1 Co1 118.7(2) . . ?
C3 C2 C1 107.6(4) . . ?
C3 C2 Co1 70.2(3) . . ?
C1 C2 Co1 69.5(2) . . ?
C2 C3 C4 110.6(4) . . ?
C2 C3 Co1 71.5(2) . . ?
C4 C3 Co1 70.7(3) . . ?
C3 C4 C5 106.8(4) . . ?
C3 C4 Co1 70.4(2) . . ?
C5 C4 Co1 70.6(2) . . ?
C1 C5 C4 107.0(4) . . ?
C1 C5 Co1 69.5(2) . . ?
C4 C5 Co1 68.9(2) . . ?
C7 C6 C1 112.0(3) . . ?
C6 C7 P1 112.9(2) . . ?
C10 C8 C9 109.0(3) . . ?
C10 C8 C11 109.2(3) . . ?
C9 C8 C11 108.4(3) . . ?
C10 C8 P1 113.2(2) . . ?
C9 C8 P1 106.2(2) . . ?
C11 C8 P1 110.5(2) . . ?
C15 C12 C13 107.0(3) . . ?
C15 C12 C14 108.2(3) . . ?
C13 C12 C14 108.1(3) . . ?
C15 C12 P1 111.5(2) . . ?
C13 C12 P1 106.6(2) . . ?
C14 C12 P1 115.1(3) . . ?
C21 C16 C17 115.4(3) . . ?
C21 C16 Si1 123.7(2) . . ?
C17 C16 Si1 120.7(2) . . ?
C18 C17 C16 121.9(3) . . ?
C19 C18 C17 120.4(3) . . ?
C18 C19 C20 118.9(3) . . ?
C19 C20 C21 120.8(3) . . ?
C20 C21 C16 122.6(3) . . ?
C27 C22 C23 115.2(3) . . ?
C27 C22 Si1 123.3(3) . . ?
C23 C22 Si1 121.5(3) . . ?
C24 C23 C22 123.0(4) . . ?
C25 C24 C23 119.5(5) . . ?
C24 C25 C26 120.7(4) . . ?
C27 C26 C25 118.3(4) . . ?
C26 C27 C22 123.3(4) . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_exp_1080
_database_code_depnum_ccdc_archive 'CCDC 2141643'
loop_
_audit_author_name
_audit_author_address
'Masafumi Ueda'
;Kitasato University
Japan
;
_audit_update_record             
;
2022-01-12 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_audit_creation_date             2021-04-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
3-butyl-2,4-dichloro-1,5-bis(methylsulfinyl)benzene
_chemical_formula_moiety         '2(C12 H16 Cl2 O2 S2)'
_chemical_formula_sum            'C24 H32 Cl4 O4 S4'
_chemical_formula_weight         654.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H16O2S2Cl2
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'
Cl Cl 0.3639 0.7018 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4018(4)
_cell_length_b                   9.7068(5)
_cell_length_c                   16.7103(9)
_cell_angle_alpha                79.588(4)
_cell_angle_beta                 76.006(4)
_cell_angle_gamma                88.447(4)
_cell_volume                     1455.16(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6707
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      70.9610
_cell_measurement_theta_min      2.7580
_shelx_estimated_absorpt_T_max   0.654
_shelx_estimated_absorpt_T_min   0.184
_exptl_absorpt_coefficient_mu    6.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13636
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.108
_diffrn_reflns_theta_min         2.770
_diffrn_ambient_temperature      120.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00   1.00   0.50    0.05    --    0.00 -78.00 112.00   50
  2  ω     17.00  76.00   0.50    0.22    --   55.92 -78.00 112.00  118
  3  ω     66.00 102.00   0.50    0.22    --  111.84 -78.00 112.00   72
  4  ω     61.00 108.00   0.50    0.22    --  111.84-111.00  90.00   94
  5  ω     40.00 103.00   0.50    0.22    --  111.84 -91.00  90.00  126
  6  ω     36.00 110.00   0.50    0.22    --   55.92-125.00   0.00  148
  7  ω     83.00 108.00   0.50    0.22    --  111.84-111.00 -30.00   50
  8  ω     63.00 104.00   0.50    0.22    --  111.84-111.00-120.00   82
  9  ω     52.00 108.00   0.50    0.22    --  111.84-111.00-150.00  112
 10  ω     27.00  57.00   0.50    0.22    --  111.84 -50.00-180.00   60
 11  ω     30.00  56.00   0.50    0.22    --  111.84 -50.00-120.00   52
 12  ω     25.00  50.00   0.50    0.22    --  111.84-111.00 -30.00   50
 13  ω     24.00 102.00   0.50    0.22    --  111.84-111.00   0.00  156
 14  ω     30.00  56.00   0.50    0.22    --  111.84 -50.00 150.00   52
 15  ω     31.00  57.00   0.50    0.22    --  111.84 -50.00  90.00   52
 16  ω     28.00  55.00   0.50    0.22    --  111.84-111.00  90.00   54
 17  ω     15.00 102.00   0.50    0.22    --  111.84 -91.00   0.00  174
 18  ω    -11.00  35.00   0.50    0.05    --    0.00  78.00-122.00   92
 19  ω    -33.00  25.00   0.50    0.22    --   55.92 -15.00   0.00  116
 20  ω    -16.00  28.00   0.50    0.22    --   55.92 -30.00 -90.00   88
 21  ω     31.00  57.00   0.50    0.05    --    0.00 -99.00 -60.00   52
 22  ω      4.00  29.00   0.50    0.05    --    0.00 -99.00 -60.00   50
 23  ω    -24.00   2.00   0.50    0.22    --  -55.92  15.00 -90.00   52
 24  ω    -48.00   4.00   0.50    0.22    --  -55.92  78.00-122.00  104
 25  ω    -24.00   2.00   0.50    0.22    --  -55.92  15.00-180.00   52
 26  ω    -56.00 -23.00   0.50    0.22    -- -106.00  50.00-120.00   66
 27  ω    -74.00 -23.00   0.50    0.22    -- -106.00  63.00 -60.00  102
 28  ω    -15.00  26.00   0.50    0.22    --  -55.92  15.00  30.00   82
 29  ω     -5.00  26.00   0.50    0.22    --  -55.92  45.00  30.00   62
 30  ω    -24.00  14.00   0.50    0.22    --  -55.92  15.00   0.00   76
 31  ω    -56.00 -24.00   0.50    0.22    -- -106.00  50.00  60.00   64
 32  ω    -65.00 -24.00   0.50    0.22    -- -106.00   0.00 120.00   82
 33  ω    -67.00 -40.00   0.50    0.22    -- -106.00  63.00  60.00   54
 34  ω    -81.00 -26.00   0.50    0.22    --  -55.92 125.00   0.00  110
 35  ω    -70.00 -40.00   0.50    0.05    --    0.00 178.00 -60.00   60
 36  ω    -86.00 -36.00   0.50    0.22    --  -55.92 125.00 -30.00  100
 37  ω    -91.00 -66.00   0.50    0.22    -- -106.00  78.00-122.00   50
 38  ω   -106.00 -27.00   0.50    0.22    -- -106.00 -12.00  30.00  158
 39  ω   -110.00 -84.00   0.50    0.22    -- -106.00   0.00 120.00   52
 40  ω   -114.00 -11.00   0.50    0.22    --  -55.92 -78.00 112.00  206
 41  ω    -91.00 -55.00   0.50    0.05    --    0.00 -78.00 112.00   72
 42  ω    -41.00  11.00   0.50    0.22    --   55.92 -15.00 150.00  104
 43  ω     73.00 176.00   0.50    0.22    --  111.84  63.00 150.00  206
 44  ω    111.00 136.00   0.50    0.22    --  111.84 178.00  30.00   50
 45  ω    148.00 177.00   0.50    0.22    --  111.84  78.00-122.00   58
 46  ω     64.00 135.00   0.50    0.22    --  111.84  78.00-122.00  142
 47  ω      8.00 134.00   0.50    0.22    --   55.92  78.00-122.00  252
 48  ω   -119.00 -92.00   0.50    0.22    -- -106.00-111.00-180.00   54
 49  ω   -176.00-138.00   0.50    0.22    -- -106.00-111.00-180.00   76
 50  ω   -177.00 -83.00   0.50    0.22    -- -106.00 -50.00  30.00  188
 51  ω   -135.00 -68.00   0.50    0.22    -- -106.00 -78.00 112.00  134
 52  ω   -164.00-139.00   0.50    0.22    -- -106.00 -78.00 112.00   50
 53  ω   -171.00-116.00   0.50    0.22    -- -106.00   0.00 120.00  110
 54  ω   -165.00-140.00   0.50    0.22    -- -106.00 -12.00  30.00   50
 55  ω   -119.00 -42.00   0.50    0.22    -- -106.00 178.00 -30.00  154
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0552578000
_diffrn_orient_matrix_UB_12      -0.0249589000
_diffrn_orient_matrix_UB_13      0.0809567000
_diffrn_orient_matrix_UB_21      0.0190770000
_diffrn_orient_matrix_UB_22      0.1592742000
_diffrn_orient_matrix_UB_23      -0.0073357000
_diffrn_orient_matrix_UB_31      -0.1584561000
_diffrn_orient_matrix_UB_32      0.0074798000
_diffrn_orient_matrix_UB_33      0.0521569000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5164
_reflns_number_total             5453
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.088
_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)+(0.0641P)²+0.5507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1237
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8B(H8BA,H8BB), C7B(H7BA,H7BB), C9B(H9BA,H9BB), C7A(H7AA,H7AB), C8A(H8AA,
 H8AB), C9A(H9AA,H9AB)
2.b Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C6B(H6B)
2.c Idealised Me refined as rotating group:
 C12B(H12A,H12B,H12C), C12A(H12D,H12E,H12F), C11B(H11A,H11B,H11C), C10B(H10A,
 H10B,H10C), C10A(H10D,H10E,H10F), C11A(H11D,H11E,H11F)
;
_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
Cl2B Cl 0.50221(7) 0.79002(6) 0.71672(4) 0.02321(16) Uani 1 1 d . . . . .
S2A S 1.24687(6) 0.54480(6) 0.88189(4) 0.01902(15) Uani 1 1 d . . . . .
S2B S 0.48367(6) 0.98211(6) 0.85452(4) 0.01886(15) Uani 1 1 d . . . . .
Cl2A Cl 1.39056(7) 0.37630(7) 0.73478(4) 0.02492(16) Uani 1 1 d . . . . .
S1B S -0.08517(6) 1.08997(6) 0.85159(4) 0.02010(15) Uani 1 1 d . . . . .
Cl1A Cl 0.86448(7) 0.36468(7) 0.65512(4) 0.02724(16) Uani 1 1 d . . . . .
S1A S 0.72658(7) 0.54409(6) 0.79592(4) 0.02038(15) Uani 1 1 d . . . . .
Cl1B Cl -0.05702(7) 0.92184(7) 0.70165(4) 0.02790(17) Uani 1 1 d . . . . .
O2B O 0.4437(2) 1.10343(19) 0.89895(12) 0.0255(4) Uani 1 1 d . . . . .
O1B O -0.0462(2) 1.18081(19) 0.90630(12) 0.0264(4) Uani 1 1 d . . . . .
O1A O 0.7133(2) 0.6473(2) 0.85325(12) 0.0265(4) Uani 1 1 d . . . . .
O2A O 1.1532(2) 0.64771(19) 0.92592(12) 0.0261(4) Uani 1 1 d . . . . .
C5A C 1.1451(3) 0.4940(2) 0.81255(14) 0.0164(5) Uani 1 1 d . . . . .
C6A C 1.0011(3) 0.5339(2) 0.82437(15) 0.0178(5) Uani 1 1 d . . . . .
H6A H 0.960345 0.588870 0.865717 0.021 Uiso 1 1 calc R U . . .
C2A C 0.9770(3) 0.4143(2) 0.71425(15) 0.0184(5) Uani 1 1 d . . . . .
C6B C 0.2028(3) 1.0268(2) 0.83767(14) 0.0170(5) Uani 1 1 d . . . . .
H6B H 0.196475 1.083632 0.879064 0.020 Uiso 1 1 calc R U . . .
C3B C 0.2231(3) 0.8625(2) 0.71163(14) 0.0182(5) Uani 1 1 d . . . . .
C4B C 0.3404(3) 0.8778(2) 0.74745(15) 0.0176(5) Uani 1 1 d . . . . .
C1B C 0.0839(3) 1.0100(2) 0.80588(15) 0.0178(5) Uani 1 1 d . . . . .
C1A C 0.9161(3) 0.4930(2) 0.77523(15) 0.0175(5) Uani 1 1 d . . . . .
C5B C 0.3324(3) 0.9598(2) 0.80866(14) 0.0176(5) Uani 1 1 d . . . . .
C3A C 1.1235(3) 0.3735(2) 0.69942(15) 0.0187(5) Uani 1 1 d . . . . .
C4A C 1.2056(3) 0.4175(3) 0.75004(15) 0.0177(5) Uani 1 1 d . . . . .
C8B C 0.2929(3) 0.8680(3) 0.55545(15) 0.0216(5) Uani 1 1 d . . . . .
H8BA H 0.224240 0.945338 0.546901 0.026 Uiso 1 1 calc R U . . .
H8BB H 0.389206 0.909960 0.552456 0.026 Uiso 1 1 calc R U . . .
C12B C 0.4436(3) 0.8275(3) 0.93430(16) 0.0212(5) Uani 1 1 d . . . . .
H12A H 0.499555 0.831111 0.976358 0.032 Uiso 1 1 calc R U . . .
H12B H 0.470944 0.744270 0.908787 0.032 Uiso 1 1 calc R U . . .
H12C H 0.338550 0.822829 0.961216 0.032 Uiso 1 1 calc R U . . .
C7B C 0.2358(3) 0.7786(3) 0.64281(15) 0.0206(5) Uani 1 1 d . . . . .
H7BA H 0.138362 0.738316 0.646308 0.025 Uiso 1 1 calc R U . . .
H7BB H 0.303195 0.699998 0.650950 0.025 Uiso 1 1 calc R U . . .
C9B C 0.3091(3) 0.7830(3) 0.48561(16) 0.0231(5) Uani 1 1 d . . . . .
H9BA H 0.375317 0.703906 0.495122 0.028 Uiso 1 1 calc R U . . .
H9BB H 0.212142 0.743380 0.487529 0.028 Uiso 1 1 calc R U . . .
C12A C 1.2209(3) 0.3794(3) 0.95287(15) 0.0219(5) Uani 1 1 d . . . . .
H12D H 1.260397 0.385949 1.001246 0.033 Uiso 1 1 calc R U . . .
H12E H 1.272125 0.306337 0.924033 0.033 Uiso 1 1 calc R U . . .
H12F H 1.115986 0.355901 0.972006 0.033 Uiso 1 1 calc R U . . .
C2B C 0.0953(3) 0.9318(3) 0.74234(15) 0.0182(5) Uani 1 1 d . . . . .
C7A C 1.1880(3) 0.2914(3) 0.63146(15) 0.0217(5) Uani 1 1 d . . . . .
H7AA H 1.111524 0.228859 0.625166 0.026 Uiso 1 1 calc R U . . .
H7AB H 1.267589 0.232191 0.647543 0.026 Uiso 1 1 calc R U . . .
C8A C 1.2494(3) 0.3890(3) 0.54741(16) 0.0247(6) Uani 1 1 d . . . . .
H8AA H 1.174221 0.458612 0.536614 0.030 Uiso 1 1 calc R U . . .
H8AB H 1.335744 0.440758 0.551745 0.030 Uiso 1 1 calc R U . . .
C11B C -0.1632(3) 0.9313(3) 0.91979(17) 0.0254(5) Uani 1 1 d . . . . .
H11A H -0.096024 0.892757 0.954461 0.038 Uiso 1 1 calc R U . . .
H11B H -0.179024 0.862967 0.886082 0.038 Uiso 1 1 calc R U . . .
H11C H -0.257109 0.951699 0.956016 0.038 Uiso 1 1 calc R U . . .
C10B C 0.3699(3) 0.8705(3) 0.39928(16) 0.0289(6) Uani 1 1 d . . . . .
H10A H 0.375588 0.812326 0.356413 0.043 Uiso 1 1 calc R U . . .
H10B H 0.468098 0.905955 0.396074 0.043 Uiso 1 1 calc R U . . .
H10C H 0.305238 0.949440 0.389740 0.043 Uiso 1 1 calc R U . . .
C9A C 1.2942(3) 0.3130(3) 0.47343(17) 0.0276(6) Uani 1 1 d . . . . .
H9AA H 1.359789 0.235401 0.487140 0.033 Uiso 1 1 calc R U . . .
H9AB H 1.350380 0.378775 0.424285 0.033 Uiso 1 1 calc R U . . .
C10A C 1.1641(3) 0.2536(3) 0.45018(18) 0.0324(6) Uani 1 1 d . . . . .
H10D H 1.199522 0.207574 0.401641 0.049 Uiso 1 1 calc R U . . .
H10E H 1.098787 0.329793 0.436251 0.049 Uiso 1 1 calc R U . . .
H10F H 1.110293 0.185202 0.497721 0.049 Uiso 1 1 calc R U . . .
C11A C 0.6552(3) 0.3810(3) 0.8619(2) 0.0309(6) Uani 1 1 d . . . . .
H11D H 0.706097 0.358414 0.907196 0.046 Uiso 1 1 calc R U . . .
H11E H 0.670497 0.306251 0.828488 0.046 Uiso 1 1 calc R U . . .
H11F H 0.550044 0.389559 0.885862 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
Cl2B C4B 1.736(2) . ?
S2A O2A 1.4899(18) . ?
S2A C5A 1.808(2) . ?
S2A C12A 1.799(3) . ?
S2B O2B 1.4955(19) . ?
S2B C5B 1.806(3) . ?
S2B C12B 1.799(3) . ?
Cl2A C4A 1.742(2) . ?
S1B O1B 1.4896(19) . ?
S1B C1B 1.809(2) . ?
S1B C11B 1.798(3) . ?
Cl1A C2A 1.741(2) . ?
S1A O1A 1.4900(19) . ?
S1A C1A 1.804(2) . ?
S1A C11A 1.800(3) . ?
Cl1B C2B 1.739(3) . ?
C5A C6A 1.375(4) . ?
C5A C4A 1.392(3) . ?
C6A H6A 0.9500 . ?
C6A C1A 1.387(4) . ?
C2A C1A 1.388(3) . ?
C2A C3A 1.398(4) . ?
C6B H6B 0.9500 . ?
C6B C1B 1.374(4) . ?
C6B C5B 1.388(3) . ?
C3B C4B 1.399(4) . ?
C3B C7B 1.506(3) . ?
C3B C2B 1.394(4) . ?
C4B C5B 1.393(3) . ?
C1B C2B 1.396(3) . ?
C3A C4A 1.399(3) . ?
C3A C7A 1.503(3) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C7B 1.536(3) . ?
C8B C9B 1.523(3) . ?
C12B H12A 0.9800 . ?
C12B H12B 0.9800 . ?
C12B H12C 0.9800 . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C9B C10B 1.521(4) . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.536(3) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.520(3) . ?
C11B H11A 0.9800 . ?
C11B H11B 0.9800 . ?
C11B H11C 0.9800 . ?
C10B H10A 0.9800 . ?
C10B H10B 0.9800 . ?
C10B H10C 0.9800 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.527(4) . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2A S2A C5A 105.37(11) . . ?
O2A S2A C12A 106.91(12) . . ?
C12A S2A C5A 94.95(11) . . ?
O2B S2B C5B 105.26(11) . . ?
O2B S2B C12B 105.95(11) . . ?
C12B S2B C5B 95.90(11) . . ?
O1B S1B C1B 105.84(11) . . ?
O1B S1B C11B 106.31(12) . . ?
C11B S1B C1B 94.69(12) . . ?
O1A S1A C1A 105.66(11) . . ?
O1A S1A C11A 105.64(13) . . ?
C11A S1A C1A 95.80(12) . . ?
C6A C5A S2A 116.74(18) . . ?
C6A C5A C4A 120.1(2) . . ?
C4A C5A S2A 123.12(19) . . ?
C5A C6A H6A 120.4 . . ?
C5A C6A C1A 119.2(2) . . ?
C1A C6A H6A 120.4 . . ?
C1A C2A Cl1A 117.92(19) . . ?
C1A C2A C3A 122.5(2) . . ?
C3A C2A Cl1A 119.57(19) . . ?
C1B C6B H6B 120.4 . . ?
C1B C6B C5B 119.3(2) . . ?
C5B C6B H6B 120.4 . . ?
C4B C3B C7B 121.8(2) . . ?
C2B C3B C4B 116.0(2) . . ?
C2B C3B C7B 122.2(2) . . ?
C3B C4B Cl2B 119.68(19) . . ?
C5B C4B Cl2B 117.84(19) . . ?
C5B C4B C3B 122.5(2) . . ?
C6B C1B S1B 117.02(18) . . ?
C6B C1B C2B 120.4(2) . . ?
C2B C1B S1B 122.60(19) . . ?
C6A C1A S1A 117.10(18) . . ?
C6A C1A C2A 120.0(2) . . ?
C2A C1A S1A 122.89(19) . . ?
C6B C5B S2B 117.36(18) . . ?
C6B C5B C4B 119.7(2) . . ?
C4B C5B S2B 122.94(19) . . ?
C2A C3A C4A 115.7(2) . . ?
C2A C3A C7A 121.5(2) . . ?
C4A C3A C7A 122.8(2) . . ?
C5A C4A Cl2A 118.22(19) . . ?
C5A C4A C3A 122.4(2) . . ?
C3A C4A Cl2A 119.35(19) . . ?
H8BA C8B H8BB 107.9 . . ?
C7B C8B H8BA 109.1 . . ?
C7B C8B H8BB 109.1 . . ?
C9B C8B H8BA 109.1 . . ?
C9B C8B H8BB 109.1 . . ?
C9B C8B C7B 112.4(2) . . ?
S2B C12B H12A 109.5 . . ?
S2B C12B H12B 109.5 . . ?
S2B C12B H12C 109.5 . . ?
H12A C12B H12B 109.5 . . ?
H12A C12B H12C 109.5 . . ?
H12B C12B H12C 109.5 . . ?
C3B C7B C8B 112.1(2) . . ?
C3B C7B H7BA 109.2 . . ?
C3B C7B H7BB 109.2 . . ?
C8B C7B H7BA 109.2 . . ?
C8B C7B H7BB 109.2 . . ?
H7BA C7B H7BB 107.9 . . ?
C8B C9B H9BA 109.1 . . ?
C8B C9B H9BB 109.1 . . ?
H9BA C9B H9BB 107.9 . . ?
C10B C9B C8B 112.4(2) . . ?
C10B C9B H9BA 109.1 . . ?
C10B C9B H9BB 109.1 . . ?
S2A C12A H12D 109.5 . . ?
S2A C12A H12E 109.5 . . ?
S2A C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C3B C2B Cl1B 120.02(19) . . ?
C3B C2B C1B 122.1(2) . . ?
C1B C2B Cl1B 117.86(19) . . ?
C3A C7A H7AA 109.4 . . ?
C3A C7A H7AB 109.4 . . ?
C3A C7A C8A 111.2(2) . . ?
H7AA C7A H7AB 108.0 . . ?
C8A C7A H7AA 109.4 . . ?
C8A C7A H7AB 109.4 . . ?
C7A C8A H8AA 108.8 . . ?
C7A C8A H8AB 108.8 . . ?
H8AA C8A H8AB 107.7 . . ?
C9A C8A C7A 113.7(2) . . ?
C9A C8A H8AA 108.8 . . ?
C9A C8A H8AB 108.8 . . ?
S1B C11B H11A 109.5 . . ?
S1B C11B H11B 109.5 . . ?
S1B C11B H11C 109.5 . . ?
H11A C11B H11B 109.5 . . ?
H11A C11B H11C 109.5 . . ?
H11B C11B H11C 109.5 . . ?
C9B C10B H10A 109.5 . . ?
C9B C10B H10B 109.5 . . ?
C9B C10B H10C 109.5 . . ?
H10A C10B H10B 109.5 . . ?
H10A C10B H10C 109.5 . . ?
H10B C10B H10C 109.5 . . ?
C8A C9A H9AA 108.9 . . ?
C8A C9A H9AB 108.9 . . ?
C8A C9A C10A 113.2(2) . . ?
H9AA C9A H9AB 107.7 . . ?
C10A C9A H9AA 108.9 . . ?
C10A C9A H9AB 108.9 . . ?
C9A C10A H10D 109.5 . . ?
C9A C10A H10E 109.5 . . ?
C9A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
S1A C11A H11D 109.5 . . ?
S1A C11A H11E 109.5 . . ?
S1A C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 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
Cl2B C4B C5B S2B 1.8(3) . . . . ?
Cl2B C4B C5B C6B -177.19(18) . . . . ?
S2A C5A C6A C1A -177.41(18) . . . . ?
S2A C5A C4A Cl2A -3.3(3) . . . . ?
S2A C5A C4A C3A 176.97(19) . . . . ?
S1B C1B C2B Cl1B 4.3(3) . . . . ?
S1B C1B C2B C3B -175.43(18) . . . . ?
Cl1A C2A C1A S1A 0.5(3) . . . . ?
Cl1A C2A C1A C6A 179.45(18) . . . . ?
Cl1A C2A C3A C4A -179.77(18) . . . . ?
Cl1A C2A C3A C7A 2.0(3) . . . . ?
O2B S2B C5B C6B -15.2(2) . . . . ?
O2B S2B C5B C4B 165.8(2) . . . . ?
O1B S1B C1B C6B 9.9(2) . . . . ?
O1B S1B C1B C2B -171.4(2) . . . . ?
O1A S1A C1A C6A 11.2(2) . . . . ?
O1A S1A C1A C2A -169.8(2) . . . . ?
O2A S2A C5A C6A -11.8(2) . . . . ?
O2A S2A C5A C4A 168.7(2) . . . . ?
C5A C6A C1A S1A 178.16(18) . . . . ?
C5A C6A C1A C2A -0.8(4) . . . . ?
C6A C5A C4A Cl2A 177.25(18) . . . . ?
C6A C5A C4A C3A -2.5(4) . . . . ?
C2A C3A C4A Cl2A -178.28(17) . . . . ?
C2A C3A C4A C5A 1.5(4) . . . . ?
C2A C3A C7A C8A 88.2(3) . . . . ?
C6B C1B C2B Cl1B -177.01(18) . . . . ?
C6B C1B C2B C3B 3.2(4) . . . . ?
C3B C4B C5B S2B -179.23(18) . . . . ?
C3B C4B C5B C6B 1.8(4) . . . . ?
C4B C3B C7B C8B -88.5(3) . . . . ?
C4B C3B C2B Cl1B 179.31(17) . . . . ?
C4B C3B C2B C1B -0.9(4) . . . . ?
C1B C6B C5B S2B -178.51(18) . . . . ?
C1B C6B C5B C4B 0.5(3) . . . . ?
C1A C2A C3A C4A -0.2(4) . . . . ?
C1A C2A C3A C7A -178.4(2) . . . . ?
C5B C6B C1B S1B 175.77(17) . . . . ?
C5B C6B C1B C2B -3.0(4) . . . . ?
C3A C2A C1A S1A -179.08(19) . . . . ?
C3A C2A C1A C6A -0.2(4) . . . . ?
C3A C7A C8A C9A -170.9(2) . . . . ?
C4A C5A C6A C1A 2.1(4) . . . . ?
C4A C3A C7A C8A -89.9(3) . . . . ?
C12B S2B C5B C6B 93.2(2) . . . . ?
C12B S2B C5B C4B -85.8(2) . . . . ?
C7B C3B C4B Cl2B -3.8(3) . . . . ?
C7B C3B C4B C5B 177.2(2) . . . . ?
C7B C3B C2B Cl1B 0.5(3) . . . . ?
C7B C3B C2B C1B -179.7(2) . . . . ?
C7B C8B C9B C10B -178.3(2) . . . . ?
C9B C8B C7B C3B 178.8(2) . . . . ?
C12A S2A C5A C6A 97.3(2) . . . . ?
C12A S2A C5A C4A -82.3(2) . . . . ?
C2B C3B C4B Cl2B 177.40(17) . . . . ?
C2B C3B C4B C5B -1.6(3) . . . . ?
C2B C3B C7B C8B 90.2(3) . . . . ?
C7A C3A C4A Cl2A -0.1(3) . . . . ?
C7A C3A C4A C5A 179.7(2) . . . . ?
C7A C8A C9A C10A 69.9(3) . . . . ?
C11B S1B C1B C6B -98.5(2) . . . . ?
C11B S1B C1B C2B 80.2(2) . . . . ?
C11A S1A C1A C6A -96.8(2) . . . . ?
C11A S1A C1A C2A 82.1(2) . . . . ?

_olex2_submission_original_sample_id 
3-butyl-2,4-dichloro-1,5-bis(methylsulfinyl)benzene
_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 2.438
_oxdiff_exptl_absorpt_empirical_full_min 0.529
####################################################################### 
# 
# 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_exp_1702_auto
_database_code_depnum_ccdc_archive 'CCDC 2153529'
loop_
_audit_author_name
_audit_author_address
'Masafumi Ueda'
;Kitasato University
Japan
;
_audit_update_record             
;
2022-02-21 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_audit_creation_date             2022-02-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H32 S10, 1.038(C7 H8)'
_chemical_formula_sum            'C51.26 H40.30 S10'
_chemical_formula_weight         976.91
_chemical_melting_point          ?
_chemical_oxdiff_formula         C58H48S10
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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_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                   13.2924(3)
_cell_length_b                   6.26750(10)
_cell_length_c                   27.5289(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.973(2)
_cell_angle_gamma                90
_cell_volume                     2258.78(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5353
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      70.8430
_cell_measurement_theta_min      3.3830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.811
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
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    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.576
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.042
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            9764
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.954
_diffrn_reflns_theta_min         3.260
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00  77.00   0.50    0.13    --    0.00  22.00  69.00   72
  2  ω    -16.00  36.00   0.50    0.13    --    0.00  22.00  69.00  104
  3  ω    -23.00 129.00   0.50    0.50    --   55.92  22.00  69.00  304
  4  ω     38.00 173.00   0.50    0.50    --  111.84  22.00  69.00  270
  5  ω     12.00  39.00   0.50    0.13    --    0.00 -99.00-180.00   54
  6  ω    -57.00 -25.00   0.50    0.50    -- -106.00  50.00-180.00   64
  7  ω    -53.00 -23.00   0.50    0.50    -- -106.00  50.00-120.00   60
  8  ω    -54.00 -23.00   0.50    0.50    -- -106.00  50.00 -90.00   62
  9  ω    -54.00 -28.00   0.50    0.50    -- -106.00  50.00 -60.00   52
 10  ω    -73.00 -26.00   0.50    0.50    -- -106.00  63.00 150.00   94
 11  ω    -53.00 -24.00   0.50    0.50    -- -106.00  50.00 150.00   58
 12  ω    -77.00 -23.00   0.50    0.50    --  -55.92 125.00  60.00  108
 13  ω    -86.00 -20.00   0.50    0.50    --  -55.92 125.00 150.00  132
 14  ω    -59.00 -33.00   0.50    0.50    --  -55.92 125.00  90.00   52
 15  ω   -121.00 -48.00   0.50    0.50    -- -106.00 -22.00 -96.00  146
 16  ω    -39.00  -8.00   0.50    0.50    --   55.92 -22.00 -96.00   62
 17  ω     45.00  70.00   0.50    0.50    --  111.84 -63.00-150.00   50
 18  ω     28.00  53.00   0.50    0.50    --  111.84 -50.00 -90.00   50
 19  ω     27.00  52.00   0.50    0.50    --  111.84 -50.00 -60.00   50
 20  ω     27.00  54.00   0.50    0.50    --  111.84 -50.00  30.00   54
 21  ω     33.00  71.00   0.50    0.50    --  111.84 -63.00 150.00   76
 22  ω    -32.00  27.00   0.50    0.50    --   55.92 -30.00 150.00  118
 23  ω    -76.00  -8.00   0.50    0.13    --    0.00 -22.00 -96.00  136
 24  ω    109.00 139.00   0.50    0.50    --  111.84 111.00 -60.00   60
 25  ω    150.00 177.00   0.50    0.50    --  111.84 111.00 -60.00   54
 26  ω    117.00 146.00   0.50    0.50    --  111.84 178.00 -90.00   58
 27  ω     68.00 116.00   0.50    0.50    --  111.84 178.00 -60.00   96
 28  ω     68.00 108.00   0.50    0.50    --  111.84 178.00 -90.00   80
 29  ω    120.00 145.00   0.50    0.50    --  111.84 178.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1089741000
_diffrn_orient_matrix_UB_12      0.0689797000
_diffrn_orient_matrix_UB_13      -0.0049748000
_diffrn_orient_matrix_UB_21      0.0329839000
_diffrn_orient_matrix_UB_22      -0.0161283000
_diffrn_orient_matrix_UB_23      0.0563285000
_diffrn_orient_matrix_UB_31      0.0297737000
_diffrn_orient_matrix_UB_32      -0.2354614000
_diffrn_orient_matrix_UB_33      -0.0053087000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3786
_reflns_number_total             4234
_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 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          8.528
_refine_ls_shift/su_mean         0.028
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0418P)²+1.2090P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0883
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C29)=Sof(C23)=Sof(C28)=Sof(C27)=Sof(C26)=Sof(C25)=Sof(C24)=Sof(H29A)=
 Sof(H29B)=Sof(H29C)=Sof(H28)=Sof(H27)=Sof(H26)=Sof(H25)=Sof(H24)=FVAR(1)
3.a Free rotating group:
 C29(C23,C28,C27,C26,C25,C24,H29A,H29B,H29C,H28,H27,H26,H25,H24)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C19(H19A,H19B), C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C16(H16), C4(H4), C13(H13), C17(H17), C3(H3), C1(H1)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_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
S2 S 0.08468(4) 0.31234(8) 0.44823(2) 0.01982(12) Uani 1 1 d . . . . .
S4 S 0.32093(4) 0.32144(7) 0.30305(2) 0.01906(12) Uani 1 1 d . . . . .
S1 S 0.18744(4) 0.75752(7) 0.48831(2) 0.02181(12) Uani 1 1 d . . . . .
S3 S 0.41524(4) 0.76933(7) 0.34637(2) 0.02137(12) Uani 1 1 d . . . . .
S5 S 0.20526(4) 0.48479(10) 0.67780(2) 0.02906(14) Uani 1 1 d . . . . .
C9 C 0.18690(14) 0.4225(3) 0.42253(7) 0.0168(4) Uani 1 1 d . . . . .
C11 C 0.29061(14) 0.4266(3) 0.35876(7) 0.0173(4) Uani 1 1 d . . . . .
C15 C 0.45361(14) 0.3736(3) 0.30973(7) 0.0185(4) Uani 1 1 d . . . . .
C12 C 0.33449(14) 0.6188(3) 0.37768(7) 0.0172(4) Uani 1 1 d . . . . .
C8 C 0.23168(14) 0.6138(3) 0.44112(7) 0.0178(4) Uani 1 1 d . . . . .
C10 C 0.21905(14) 0.3200(3) 0.38223(7) 0.0161(4) Uani 1 1 d . . . . .
C5 C 0.12517(14) 0.3578(3) 0.51216(7) 0.0190(4) Uani 1 1 d . . . . .
C6 C 0.16979(14) 0.5509(3) 0.52948(7) 0.0199(4) Uani 1 1 d . . . . .
C7 C 0.30925(14) 0.7059(3) 0.42038(7) 0.0177(4) Uani 1 1 d . . . . .
H7 H 0.344743 0.827299 0.435253 0.021 Uiso 1 1 calc R U . . .
C14 C 0.49441(15) 0.5675(3) 0.32929(7) 0.0193(4) Uani 1 1 d . . . . .
C16 C 0.51757(16) 0.2249(3) 0.29310(7) 0.0207(4) Uani 1 1 d . . . . .
H16 H 0.490322 0.093172 0.279700 0.025 Uiso 1 1 calc R U . . .
C4 C 0.10663(15) 0.2025(3) 0.54559(7) 0.0217(4) Uani 1 1 d . . . . .
H4 H 0.076560 0.070495 0.533952 0.026 Uiso 1 1 calc R U . . .
C13 C 0.59830(15) 0.6075(3) 0.33329(7) 0.0210(4) Uani 1 1 d . . . . .
H13 H 0.626049 0.737513 0.347491 0.025 Uiso 1 1 calc R U . . .
C20 C 0.07513(15) 0.1139(3) 0.32765(7) 0.0219(4) Uani 1 1 d . . . . .
H20A H 0.024244 0.197899 0.341891 0.026 Uiso 1 1 calc R U . . .
H20B H 0.086451 0.185785 0.297033 0.026 Uiso 1 1 calc R U . . .
C17 C 0.62128(16) 0.2677(3) 0.29595(7) 0.0234(4) Uani 1 1 d . . . . .
H17 H 0.664232 0.166972 0.283806 0.028 Uiso 1 1 calc R U . . .
C19 C 0.17582(14) 0.1059(3) 0.36447(7) 0.0175(4) Uani 1 1 d . . . . .
H19A H 0.164869 0.021140 0.393457 0.021 Uiso 1 1 calc R U . . .
H19B H 0.227166 0.029782 0.348838 0.021 Uiso 1 1 calc R U . . .
C21 C 0.03374(16) -0.1117(3) 0.31539(8) 0.0254(4) Uani 1 1 d . . . . .
H21A H 0.032065 -0.189130 0.346579 0.030 Uiso 1 1 calc R U . . .
H21B H -0.037345 -0.100927 0.297425 0.030 Uiso 1 1 calc R U . . .
C3 C 0.13195(15) 0.2399(3) 0.59594(8) 0.0238(4) Uani 1 1 d . . . . .
H3 H 0.119111 0.133446 0.618655 0.029 Uiso 1 1 calc R U . . .
C1 C 0.19573(15) 0.5881(3) 0.57978(7) 0.0223(4) Uani 1 1 d . . . . .
H1 H 0.226828 0.719231 0.591408 0.027 Uiso 1 1 calc R U . . .
C2 C 0.17617(14) 0.4332(4) 0.61325(7) 0.0233(4) Uani 1 1 d . . . . .
C18 C 0.66182(15) 0.4586(3) 0.31665(7) 0.0223(4) Uani 1 1 d . . . . .
C22 C 0.09608(18) -0.2402(3) 0.28447(8) 0.0295(5) Uani 1 1 d . . . . .
H22A H 0.093305 -0.171198 0.252325 0.044 Uiso 1 1 calc R U . . .
H22B H 0.067986 -0.384752 0.279713 0.044 Uiso 1 1 calc R U . . .
H22C H 0.167176 -0.247647 0.301425 0.044 Uiso 1 1 calc R U . . .
C29 C 0.5413(6) 1.2193(11) 0.43313(18) 0.091(4) Uani 0.519(2) 1 d G . P A -1
C23 C 0.5121(3) 1.0974(5) 0.47541(14) 0.0300(10) Uani 0.519(2) 1 d G . P A -1
C28 C 0.5549(3) 0.8989(5) 0.48894(17) 0.0369(16) Uani 0.519(2) 1 d G . P A -1
C27 C 0.5263(5) 0.7836(6) 0.5273(2) 0.074(3) Uani 0.519(2) 1 d G . P A -1
C26 C 0.4540(5) 0.8654(13) 0.55305(14) 0.139(9) Uani 0.519(2) 1 d G . P A -1
C25 C 0.4109(4) 1.0633(13) 0.5401(2) 0.104(5) Uani 0.519(2) 1 d G . P A -1
C24 C 0.4398(3) 1.1778(7) 0.5017(2) 0.057(3) Uani 0.519(2) 1 d G . P A -1
H29A H 0.534529 1.390955 0.438176 0.30(9) Uiso 0.519(2) 1 d G . P A -1
H29B H 0.619720 1.184532 0.428770 0.31(10) Uiso 0.519(2) 1 d G . P A -1
H29C H 0.491801 1.177134 0.398469 0.18(5) Uiso 0.519(2) 1 d G . P A -1
H28 H 0.611760 0.833863 0.469145 0.041(18) Uiso 0.519(2) 1 d G . P A -1
H27 H 0.560828 0.629555 0.537287 0.11(3) Uiso 0.519(2) 1 d G . P A -1
H26 H 0.431686 0.775929 0.583144 2.0(13) Uiso 0.519(2) 1 d G . P A -1
H25 H 0.354605 1.129234 0.560048 0.13(3) Uiso 0.519(2) 1 d G . P A -1
H24 H 0.405897 1.332722 0.491846 0.14(4) Uiso 0.519(2) 1 d G . P A -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
S2 C9 1.7768(19) . ?
S2 C5 1.7718(19) . ?
S4 C11 1.7784(19) . ?
S4 C15 1.7717(19) . ?
S1 C8 1.7635(19) . ?
S1 C6 1.763(2) . ?
S3 C12 1.7623(19) . ?
S3 C14 1.761(2) . ?
S5 C2 1.781(2) . ?
S5 C18 1.783(2) 3_666 ?
C9 C8 1.396(3) . ?
C9 C10 1.411(3) . ?
C11 C12 1.399(3) . ?
C11 C10 1.408(3) . ?
C15 C14 1.400(3) . ?
C15 C16 1.392(3) . ?
C12 C7 1.389(3) . ?
C8 C7 1.388(3) . ?
C10 C19 1.508(2) . ?
C5 C6 1.395(3) . ?
C5 C4 1.391(3) . ?
C6 C1 1.388(3) . ?
C7 H7 0.9500 . ?
C14 C13 1.389(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.388(3) . ?
C13 H13 0.9500 . ?
C13 C18 1.389(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C19 1.533(3) . ?
C20 C21 1.533(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.518(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.394(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.394(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C29 C23 1.4989 . ?
C29 H29A 1.0909 . ?
C29 H29B 1.0910 . ?
C29 H29C 1.0937 . ?
C23 C28 1.3921 . ?
C23 C24 1.3924 . ?
C28 C27 1.3867 . ?
C28 H28 1.0847 . ?
C27 C26 1.3868 . ?
C27 H27 1.0837 . ?
C26 C25 1.3870 . ?
C26 H26 1.0835 . ?
C25 C24 1.3865 . ?
C25 H25 1.0838 . ?
C24 H24 1.0849 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S2 C9 102.20(9) . . ?
C15 S4 C11 102.25(9) . . ?
C6 S1 C8 101.35(9) . . ?
C14 S3 C12 100.89(9) . . ?
C2 S5 C18 99.34(9) . 3_666 ?
C8 C9 S2 119.66(14) . . ?
C8 C9 C10 120.77(17) . . ?
C10 C9 S2 119.52(14) . . ?
C12 C11 S4 119.87(14) . . ?
C12 C11 C10 120.60(17) . . ?
C10 C11 S4 119.47(14) . . ?
C14 C15 S4 120.84(15) . . ?
C16 C15 S4 119.74(15) . . ?
C16 C15 C14 119.34(18) . . ?
C11 C12 S3 121.93(15) . . ?
C7 C12 S3 117.42(14) . . ?
C7 C12 C11 120.48(17) . . ?
C9 C8 S1 122.24(15) . . ?
C7 C8 S1 117.19(14) . . ?
C7 C8 C9 120.42(17) . . ?
C9 C10 C19 120.68(17) . . ?
C11 C10 C9 117.74(17) . . ?
C11 C10 C19 121.57(17) . . ?
C6 C5 S2 121.13(15) . . ?
C4 C5 S2 119.12(15) . . ?
C4 C5 C6 119.64(18) . . ?
C5 C6 S1 120.90(15) . . ?
C1 C6 S1 118.70(16) . . ?
C1 C6 C5 120.30(18) . . ?
C12 C7 H7 120.3 . . ?
C8 C7 C12 119.36(18) . . ?
C8 C7 H7 120.3 . . ?
C15 C14 S3 121.11(15) . . ?
C13 C14 S3 118.76(15) . . ?
C13 C14 C15 120.06(18) . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.49(18) . . ?
C17 C16 H16 119.8 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.16(19) . . ?
C3 C4 H4 119.9 . . ?
C14 C13 H13 119.8 . . ?
C18 C13 C14 120.36(19) . . ?
C18 C13 H13 119.8 . . ?
H20A C20 H20B 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 C19 110.74(16) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.84(19) . . ?
C18 C17 H17 120.1 . . ?
C10 C19 C20 115.16(15) . . ?
C10 C19 H19A 108.5 . . ?
C10 C19 H19B 108.5 . . ?
C20 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 C20 113.76(17) . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C4 C3 H3 119.9 . . ?
C4 C3 C2 120.20(19) . . ?
C2 C3 H3 119.9 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 120.00(19) . . ?
C2 C1 H1 120.0 . . ?
C3 C2 S5 120.31(16) . . ?
C1 C2 S5 119.99(16) . . ?
C1 C2 C3 119.69(18) . . ?
C13 C18 S5 119.22(16) . 3_666 ?
C13 C18 C17 119.87(19) . . ?
C17 C18 S5 120.91(16) . 3_666 ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C29 H29A 111.4 . . ?
C23 C29 H29B 111.4 . . ?
C23 C29 H29C 110.9 . . ?
H29A C29 H29B 108.2 . . ?
H29A C29 H29C 107.4 . . ?
H29B C29 H29C 107.3 . . ?
C28 C23 C29 120.9 . . ?
C28 C23 C24 118.1 . . ?
C24 C23 C29 120.9 . . ?
C23 C28 H28 119.3 . . ?
C27 C28 C23 121.1 . . ?
C27 C28 H28 119.6 . . ?
C28 C27 C26 120.2 . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 120.1 . . ?
C27 C26 C25 119.4 . . ?
C27 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C26 C25 H25 120.1 . . ?
C24 C25 C26 120.1 . . ?
C24 C25 H25 119.8 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.1 . . ?
C25 C24 H24 119.7 . . ?

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
S2 C9 C8 S1 -2.3(2) . . . . ?
S2 C9 C8 C7 -177.79(14) . . . . ?
S2 C9 C10 C11 171.69(14) . . . . ?
S2 C9 C10 C19 -6.9(2) . . . . ?
S2 C5 C6 S1 0.1(2) . . . . ?
S2 C5 C6 C1 176.34(15) . . . . ?
S2 C5 C4 C3 -176.02(15) . . . . ?
S4 C11 C12 S3 3.1(2) . . . . ?
S4 C11 C12 C7 178.15(14) . . . . ?
S4 C11 C10 C9 -171.76(14) . . . . ?
S4 C11 C10 C19 6.8(2) . . . . ?
S4 C15 C14 S3 -1.8(2) . . . . ?
S4 C15 C14 C13 -178.63(15) . . . . ?
S4 C15 C16 C17 176.97(15) . . . . ?
S1 C8 C7 C12 -168.81(14) . . . . ?
S1 C6 C1 C2 175.61(15) . . . . ?
S3 C12 C7 C8 168.06(14) . . . . ?
S3 C14 C13 C18 -175.05(15) . . . . ?
C9 S2 C5 C6 42.23(17) . . . . ?
C9 S2 C5 C4 -141.50(16) . . . . ?
C9 C8 C7 C12 6.9(3) . . . . ?
C9 C10 C19 C20 85.5(2) . . . . ?
C11 S4 C15 C14 -41.18(17) . . . . ?
C11 S4 C15 C16 142.08(15) . . . . ?
C11 C12 C7 C8 -7.2(3) . . . . ?
C11 C10 C19 C20 -93.0(2) . . . . ?
C15 S4 C11 C12 40.27(17) . . . . ?
C15 S4 C11 C10 -142.52(15) . . . . ?
C15 C14 C13 C18 1.9(3) . . . . ?
C15 C16 C17 C18 1.5(3) . . . . ?
C12 S3 C14 C15 44.23(17) . . . . ?
C12 S3 C14 C13 -138.87(16) . . . . ?
C12 C11 C10 C9 5.4(3) . . . . ?
C12 C11 C10 C19 -176.02(17) . . . . ?
C8 S1 C6 C5 -42.55(17) . . . . ?
C8 S1 C6 C1 141.14(16) . . . . ?
C8 C9 C10 C11 -5.7(3) . . . . ?
C8 C9 C10 C19 175.70(17) . . . . ?
C10 C9 C8 S1 175.12(14) . . . . ?
C10 C9 C8 C7 -0.4(3) . . . . ?
C10 C11 C12 S3 -174.08(14) . . . . ?
C10 C11 C12 C7 1.0(3) . . . . ?
C5 S2 C9 C8 -40.72(17) . . . . ?
C5 S2 C9 C10 141.84(15) . . . . ?
C5 C6 C1 C2 -0.7(3) . . . . ?
C5 C4 C3 C2 0.0(3) . . . . ?
C6 S1 C8 C9 44.06(17) . . . . ?
C6 S1 C8 C7 -140.30(15) . . . . ?
C6 C5 C4 C3 0.3(3) . . . . ?
C6 C1 C2 S5 -177.75(15) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C14 S3 C12 C11 -45.13(17) . . . . ?
C14 S3 C12 C7 139.67(15) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C14 C13 C18 S5 179.85(15) . . . 3_666 ?
C14 C13 C18 C17 -0.2(3) . . . . ?
C16 C15 C14 S3 174.99(14) . . . . ?
C16 C15 C14 C13 -1.9(3) . . . . ?
C16 C17 C18 S5 178.46(15) . . . 3_666 ?
C16 C17 C18 C13 -1.5(3) . . . . ?
C4 C5 C6 S1 -176.17(15) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C3 C2 S5 178.13(15) . . . . ?
C4 C3 C2 C1 -0.6(3) . . . . ?
C19 C20 C21 C22 -70.3(2) . . . . ?
C21 C20 C19 C10 -175.34(16) . . . . ?
C18 S5 C2 C3 123.75(17) 3_666 . . . ?
C18 S5 C2 C1 -57.53(18) 3_666 . . . ?
C29 C23 C28 C27 -178.5 . . . . ?
C29 C23 C24 C25 178.5 . . . . ?
C23 C28 C27 C26 -0.1 . . . . ?
C28 C23 C24 C25 -0.3 . . . . ?
C28 C27 C26 C25 -0.1 . . . . ?
C27 C26 C25 C24 0.1 . . . . ?
C26 C25 C24 C23 0.1 . . . . ?
C24 C23 C28 C27 0.3 . . . . ?

_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 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.509
####################################################################### 
# 
# 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_exp_1062
_database_code_depnum_ccdc_archive 'CCDC 2141641'
loop_
_audit_author_name
_audit_author_address
'Masafumi Ueda'
;Kitasato University
Japan
;
_audit_update_record             
;
2022-01-12 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_audit_creation_date             2021-03-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 S5'
_chemical_formula_sum            'C22 H16 S5'
_chemical_formula_weight         440.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         C44H32S10
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4234(5)
_cell_length_b                   10.8106(5)
_cell_length_c                   11.3323(3)
_cell_angle_alpha                93.809(3)
_cell_angle_beta                 104.307(4)
_cell_angle_gamma                118.489(5)
_cell_volume                     1061.75(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3559
_cell_measurement_temperature    120
_cell_measurement_theta_max      70.0450
_cell_measurement_theta_min      5.0610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.055
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.067
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8959
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.007
_diffrn_reflns_theta_min         4.124
_diffrn_ambient_temperature      120
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00   6.00   0.50    0.21    --    0.00  48.00  85.00   86
  2  ω     47.00  82.00   0.50    0.21    --    0.00  48.00  85.00   70
  3  ω     85.00 123.00   0.50    0.86    --   55.92  48.00  85.00   76
  4  ω     69.00 176.00   0.50    0.86    --  111.84  48.00  85.00  214
  5  ω    103.00 173.00   0.50    0.86    --  111.84 111.00 -60.00  140
  6  ω    119.00 146.00   0.50    0.86    --  111.84 178.00 -30.00   54
  7  ω     64.00 112.00   0.50    0.86    --  111.84 178.00 -60.00   96
  8  ω     64.00  89.00   0.50    0.86    --  111.84 178.00 -30.00   50
  9  ω      6.00  79.00   0.50    0.86    --   55.92  48.00  85.00  146
 10  ω     26.00  51.00   0.50    0.86    --  111.84 -48.00 -63.00   50
 11  ω     37.00  96.00   0.50    0.86    --  111.84 -91.00 -60.00  118
 12  ω     64.00 106.00   0.50    0.86    --  111.84-111.00   0.00   84
 13  ω     74.00 111.00   0.50    0.86    --   55.92-125.00 -90.00   74
 14  ω     67.00 105.00   0.50    0.86    --  111.84-111.00-180.00   76
 15  ω     41.00  68.00   0.50    0.86    --  111.84 -63.00-120.00   54
 16  ω     30.00  56.00   0.50    0.86    --  111.84 -50.00-150.00   52
 17  ω     15.00  63.00   0.50    0.86    --   55.92 -61.00-120.00   96
 18  ω     60.00 108.00   0.50    0.86    --  111.84-111.00 -60.00   96
 19  ω     44.00  73.00   0.50    0.86    --  111.84 -63.00   0.00   58
 20  ω     30.00  56.00   0.50    0.86    --  111.84-111.00 -60.00   52
 21  ω     27.00  56.00   0.50    0.86    --  111.84 -50.00 -30.00   58
 22  ω     41.00 171.00   0.50    0.86    --  111.84  37.00 -60.00  260
 23  ω     65.00 104.00   0.50    0.86    --  111.84-111.00  90.00   78
 24  ω     70.00  96.00   0.50    0.86    --  111.84-111.00 150.00   52
 25  ω     47.00  87.00   0.50    0.86    --  111.84-111.00 120.00   80
 26  ω     25.00  60.00   0.50    0.86    --  111.84-111.00 150.00   70
 27  ω    -22.00  43.00   0.50    0.86    --   55.92 -48.00 -63.00  130
 28  ω      2.00  39.00   0.50    0.21    --    0.00 -99.00 -90.00   74
 29  ω    -29.00   5.00   0.50    0.86    --   55.92 -61.00-120.00   68
 30  ω    -35.00  -9.00   0.50    0.21    --    0.00 -48.00 -63.00   52
 31  ω    -64.00 -27.00   0.50    0.86    --  -55.92 -48.00 -63.00   74
 32  ω    -12.00  20.00   0.50    0.86    --  -55.92  30.00 -90.00   64
 33  ω    -24.00  27.00   0.50    0.86    --  -55.92  15.00-120.00  102
 34  ω    -48.00 -23.00   0.50    0.86    -- -106.00  50.00-120.00   50
 35  ω    -78.00 -13.00   0.50    0.86    --  -55.92 125.00-150.00  130
 36  ω    -72.00 -43.00   0.50    0.86    -- -106.00 178.00 -30.00   58
 37  ω    -86.00 -40.00   0.50    0.86    --  -55.92 125.00  60.00   92
 38  ω    -49.00  27.00   0.50    0.86    --  -55.92  48.00  85.00  152
 39  ω    -54.00 -28.00   0.50    0.86    -- -106.00  48.00  85.00   52
 40  ω    -70.00 -23.00   0.50    0.86    -- -106.00 111.00  90.00   94
 41  ω    -67.00 -42.00   0.50    0.86    -- -106.00 178.00  60.00   50
 42  ω   -112.00 -74.00   0.50    0.86    -- -106.00 178.00  60.00   76
 43  ω   -114.00 -77.00   0.50    0.86    -- -106.00 178.00 -30.00   74
 44  ω   -118.00 -43.00   0.50    0.86    -- -106.00 178.00 -90.00  150
 45  ω   -119.00 -79.00   0.50    0.86    --  -55.92 -48.00 -63.00   80
 46  ω    -91.00 -63.00   0.50    0.86    -- -106.00 -48.00 -63.00   56
 47  ω   -128.00 -74.00   0.50    0.86    --  -55.92-125.00  60.00  108
 48  ω   -116.00 -87.00   0.50    0.86    -- -106.00-111.00  90.00   58
 49  ω   -143.00 -73.00   0.50    0.86    --  -55.92-125.00  30.00  140
 50  ω      1.00  27.00   0.50    0.21    --    0.00 -99.00  60.00   52
 51  ω   -133.00 -85.00   0.50    0.86    -- -106.00-111.00-120.00   96
 52  ω   -144.00 -83.00   0.50    0.86    --  -55.92 -94.00   0.00  122
 53  ω   -159.00-133.00   0.50    0.86    -- -106.00 -48.00 -63.00   52
 54  ω   -177.00-141.00   0.50    0.86    -- -106.00-111.00-120.00   72
 55  ω   -172.00-147.00   0.50    0.86    -- -106.00-111.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1618715000
_diffrn_orient_matrix_UB_12      0.0428135000
_diffrn_orient_matrix_UB_13      0.0843024000
_diffrn_orient_matrix_UB_21      -0.0606847000
_diffrn_orient_matrix_UB_22      -0.1565410000
_diffrn_orient_matrix_UB_23      0.0160214000
_diffrn_orient_matrix_UB_31      0.0396577000
_diffrn_orient_matrix_UB_32      -0.0352503000
_diffrn_orient_matrix_UB_33      -0.1152656000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3487
_reflns_number_total             3960
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.041
_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)+(0.0366P)²+0.4889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0849
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C13(H13), C16(H16), C4(H4), C17(H17), C3(H3)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
S2 S 0.39414(6) 0.90164(6) 0.75755(4) 0.02415(12) Uani 1 1 d . . . . .
S1 S 0.69701(6) 0.96492(5) 0.68651(4) 0.02386(12) Uani 1 1 d . . . . .
S3 S 0.35731(6) 0.71529(6) 0.20707(4) 0.02575(13) Uani 1 1 d . . . . .
S5 S 0.89828(6) 0.80209(6) 1.10800(4) 0.02579(13) Uani 1 1 d . . . . .
S4 S 0.04314(6) 0.60921(6) 0.27352(4) 0.02465(13) Uani 1 1 d . . . . .
C9 C 0.3773(2) 0.8269(2) 0.60606(17) 0.0219(4) Uani 1 1 d . . . . .
C1 C 0.7728(2) 0.8697(2) 0.89467(18) 0.0242(4) Uani 1 1 d . . . . .
H1 H 0.856187 0.878319 0.868716 0.029 Uiso 1 1 calc R U . . .
C15 C 0.0654(2) 0.4918(2) 0.17497(18) 0.0235(4) Uani 1 1 d . . . . .
C11 C 0.2245(2) 0.7026(2) 0.39282(18) 0.0228(4) Uani 1 1 d . . . . .
C12 C 0.3596(2) 0.7430(2) 0.36263(18) 0.0226(4) Uani 1 1 d . . . . .
C6 C 0.6638(2) 0.8948(2) 0.81967(18) 0.0236(4) Uani 1 1 d . . . . .
C14 C 0.2020(2) 0.5373(2) 0.14708(18) 0.0241(4) Uani 1 1 d . . . . .
C7 C 0.5012(2) 0.8148(2) 0.45499(18) 0.0235(4) Uani 1 1 d . . . . .
H7 H 0.591399 0.833148 0.435480 0.028 Uiso 1 1 calc R U . . .
C10 C 0.2311(2) 0.7428(2) 0.51603(18) 0.0225(4) Uani 1 1 d . . . . .
C19 C 0.0863(2) 0.7053(2) 0.54775(19) 0.0246(4) Uani 1 1 d . . . . .
H19A H 0.101310 0.692036 0.634707 0.029 Uiso 1 1 calc R U . . .
H19B H 0.000638 0.612717 0.492366 0.029 Uiso 1 1 calc R U . . .
C13 C 0.2131(2) 0.4460(2) 0.06279(18) 0.0251(4) Uani 1 1 d . . . . .
H13 H 0.307175 0.476682 0.045502 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5367(2) 0.8752(2) 0.85402(18) 0.0237(4) Uani 1 1 d . . . . .
C8 C 0.5114(2) 0.8599(2) 0.57622(18) 0.0228(4) Uani 1 1 d . . . . .
C18 C 0.0859(2) 0.3094(2) 0.00373(18) 0.0243(4) Uani 1 1 d . . . . .
C2 C 0.7592(2) 0.8317(2) 1.00825(18) 0.0243(4) Uani 1 1 d . . . . .
C16 C -0.0600(2) 0.3539(2) 0.11775(18) 0.0254(4) Uani 1 1 d . . . . .
H16 H -0.152553 0.321669 0.137889 0.031 Uiso 1 1 calc R U . . .
C4 C 0.5245(2) 0.8382(2) 0.96729(19) 0.0275(4) Uani 1 1 d . . . . .
H4 H 0.438964 0.825869 0.991727 0.033 Uiso 1 1 calc R U . . .
C17 C -0.0508(2) 0.2632(2) 0.03135(19) 0.0263(4) Uani 1 1 d . . . . .
H17 H -0.137421 0.170126 -0.008587 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6367(2) 0.8191(2) 1.04540(19) 0.0275(4) Uani 1 1 d . . . . .
H3 H 0.629548 0.797365 1.124211 0.033 Uiso 1 1 calc R U . . .
C20 C 0.0420(3) 0.8213(3) 0.5340(2) 0.0381(6) Uani 1 1 d . . . . .
H20A H 0.131847 0.916078 0.581754 0.046 Uiso 1 1 calc R U . . .
H20B H 0.015046 0.826561 0.445137 0.046 Uiso 1 1 calc R U . . .
C21 C -0.0932(4) 0.7911(4) 0.5802(4) 0.0764(12) Uani 1 1 d . . . . .
H21A H -0.065088 0.786570 0.669188 0.092 Uiso 1 1 calc R U . . .
H21B H -0.111121 0.872951 0.574854 0.092 Uiso 1 1 calc R U . . .
C22 C -0.2397(5) 0.6553(5) 0.5103(6) 0.130(2) Uani 1 1 d . . . . .
H22A H -0.263315 0.653948 0.420788 0.195 Uiso 1 1 calc R U . . .
H22B H -0.323489 0.650418 0.538184 0.195 Uiso 1 1 calc R U . . .
H22C H -0.228548 0.572313 0.525923 0.195 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
S2 C9 1.7783(19) . ?
S2 C5 1.769(2) . ?
S1 C6 1.769(2) . ?
S1 C8 1.765(2) . ?
S3 C12 1.7608(19) . ?
S3 C14 1.760(2) . ?
S5 C18 1.781(2) 2_666 ?
S5 C2 1.778(2) . ?
S4 C15 1.771(2) . ?
S4 C11 1.776(2) . ?
C9 C10 1.405(3) . ?
C9 C8 1.404(3) . ?
C1 H1 0.9500 . ?
C1 C6 1.391(3) . ?
C1 C2 1.397(3) . ?
C15 C14 1.394(3) . ?
C15 C16 1.394(3) . ?
C11 C12 1.401(3) . ?
C11 C10 1.409(3) . ?
C12 C7 1.383(3) . ?
C6 C5 1.396(3) . ?
C14 C13 1.392(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(3) . ?
C10 C19 1.508(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.534(3) . ?
C13 H13 0.9500 . ?
C13 C18 1.397(3) . ?
C5 C4 1.387(3) . ?
C18 C17 1.393(3) . ?
C2 C3 1.391(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.392(3) . ?
C17 H17 0.9500 . ?
C3 H3 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.521(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.491(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S2 C9 102.01(9) . . ?
C8 S1 C6 100.65(10) . . ?
C14 S3 C12 101.39(10) . . ?
C2 S5 C18 99.50(9) . 2_666 ?
C15 S4 C11 102.60(9) . . ?
C10 C9 S2 119.78(15) . . ?
C8 C9 S2 119.16(15) . . ?
C8 C9 C10 120.96(18) . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C2 119.71(19) . . ?
C2 C1 H1 120.1 . . ?
C14 C15 S4 121.43(16) . . ?
C14 C15 C16 119.44(18) . . ?
C16 C15 S4 119.00(16) . . ?
C12 C11 S4 119.94(15) . . ?
C12 C11 C10 120.68(18) . . ?
C10 C11 S4 119.27(15) . . ?
C11 C12 S3 121.83(15) . . ?
C7 C12 S3 117.70(15) . . ?
C7 C12 C11 120.35(18) . . ?
C1 C6 S1 118.63(16) . . ?
C1 C6 C5 120.51(19) . . ?
C5 C6 S1 120.69(16) . . ?
C15 C14 S3 120.81(16) . . ?
C13 C14 S3 118.65(16) . . ?
C13 C14 C15 120.33(19) . . ?
C12 C7 H7 120.0 . . ?
C12 C7 C8 119.91(18) . . ?
C8 C7 H7 120.0 . . ?
C9 C10 C11 117.76(18) . . ?
C9 C10 C19 121.29(18) . . ?
C11 C10 C19 120.82(18) . . ?
C10 C19 H19A 109.0 . . ?
C10 C19 H19B 109.0 . . ?
C10 C19 C20 112.77(18) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C14 C13 H13 120.1 . . ?
C14 C13 C18 119.89(19) . . ?
C18 C13 H13 120.1 . . ?
C6 C5 S2 121.09(16) . . ?
C4 C5 S2 119.57(16) . . ?
C4 C5 C6 119.31(19) . . ?
C9 C8 S1 122.38(15) . . ?
C7 C8 S1 117.61(15) . . ?
C7 C8 C9 119.96(19) . . ?
C13 C18 S5 118.78(16) . 2_666 ?
C17 C18 S5 121.18(16) . 2_666 ?
C17 C18 C13 120.03(18) . . ?
C1 C2 S5 121.02(16) . . ?
C3 C2 S5 119.22(16) . . ?
C3 C2 C1 119.75(19) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.58(19) . . ?
C17 C16 H16 119.7 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.45(19) . . ?
C3 C4 H4 119.8 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.7(2) . . ?
C16 C17 H17 120.1 . . ?
C2 C3 C4 120.12(19) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C19 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 C19 112.4(2) . . ?
C21 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
C20 C21 H21A 108.6 . . ?
C20 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C22 C21 C20 114.7(3) . . ?
C22 C21 H21A 108.6 . . ?
C22 C21 H21B 108.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
S2 C9 C10 C11 171.39(15) . . . . ?
S2 C9 C10 C19 -4.5(3) . . . . ?
S2 C9 C8 S1 3.7(2) . . . . ?
S2 C9 C8 C7 -173.44(15) . . . . ?
S2 C5 C4 C3 -179.04(17) . . . . ?
S1 C6 C5 S2 6.7(2) . . . . ?
S1 C6 C5 C4 -171.60(16) . . . . ?
S3 C12 C7 C8 169.60(15) . . . . ?
S3 C14 C13 C18 -173.30(15) . . . . ?
S5 C18 C17 C16 -178.99(15) 2_666 . . . ?
S5 C2 C3 C4 -178.36(17) . . . . ?
S4 C15 C14 S3 -1.1(2) . . . . ?
S4 C15 C14 C13 -175.70(15) . . . . ?
S4 C15 C16 C17 174.41(15) . . . . ?
S4 C11 C12 S3 4.5(2) . . . . ?
S4 C11 C12 C7 -179.53(15) . . . . ?
S4 C11 C10 C9 -174.80(15) . . . . ?
S4 C11 C10 C19 1.1(3) . . . . ?
C9 S2 C5 C6 39.37(19) . . . . ?
C9 S2 C5 C4 -142.38(17) . . . . ?
C9 C10 C19 C20 86.6(2) . . . . ?
C1 C6 C5 S2 -178.14(15) . . . . ?
C1 C6 C5 C4 3.6(3) . . . . ?
C1 C2 C3 C4 2.7(3) . . . . ?
C15 S4 C11 C12 38.54(18) . . . . ?
C15 S4 C11 C10 -145.31(16) . . . . ?
C15 C14 C13 C18 1.5(3) . . . . ?
C15 C16 C17 C18 1.3(3) . . . . ?
C11 S4 C15 C14 -40.76(19) . . . . ?
C11 S4 C15 C16 143.52(16) . . . . ?
C11 C12 C7 C8 -6.5(3) . . . . ?
C11 C10 C19 C20 -89.1(2) . . . . ?
C12 S3 C14 C15 43.34(18) . . . . ?
C12 S3 C14 C13 -141.93(16) . . . . ?
C12 C11 C10 C9 1.3(3) . . . . ?
C12 C11 C10 C19 177.18(18) . . . . ?
C12 C7 C8 S1 -174.41(15) . . . . ?
C12 C7 C8 C9 2.9(3) . . . . ?
C6 S1 C8 C9 41.27(19) . . . . ?
C6 S1 C8 C7 -141.49(16) . . . . ?
C6 C1 C2 S5 -178.79(15) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C5 C4 C3 -0.8(3) . . . . ?
C14 S3 C12 C11 -45.46(18) . . . . ?
C14 S3 C12 C7 138.49(16) . . . . ?
C14 C15 C16 C17 -1.4(3) . . . . ?
C14 C13 C18 S5 177.63(15) . . . 2_666 ?
C14 C13 C18 C17 -1.5(3) . . . . ?
C10 C9 C8 S1 -179.93(15) . . . . ?
C10 C9 C8 C7 2.9(3) . . . . ?
C10 C11 C12 S3 -171.56(15) . . . . ?
C10 C11 C12 C7 4.4(3) . . . . ?
C10 C19 C20 C21 -173.5(2) . . . . ?
C19 C20 C21 C22 -62.5(4) . . . . ?
C13 C18 C17 C16 0.2(3) . . . . ?
C5 S2 C9 C10 139.01(16) . . . . ?
C5 S2 C9 C8 -44.61(18) . . . . ?
C5 C4 C3 C2 -2.4(3) . . . . ?
C8 S1 C6 C1 137.88(16) . . . . ?
C8 S1 C6 C5 -46.82(18) . . . . ?
C8 C9 C10 C11 -4.9(3) . . . . ?
C8 C9 C10 C19 179.24(18) . . . . ?
C18 S5 C2 C1 -46.48(19) 2_666 . . . ?
C18 S5 C2 C3 134.60(17) 2_666 . . . ?
C2 C1 C6 S1 172.01(16) . . . . ?
C2 C1 C6 C5 -3.3(3) . . . . ?
C16 C15 C14 S3 174.65(15) . . . . ?
C16 C15 C14 C13 0.0(3) . . . . ?

_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 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.837
####################################################################### 
# 
# 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_exp_1589_auto
_database_code_depnum_ccdc_archive 'CCDC 2141642'
loop_
_audit_author_name
_audit_author_address
'Masafumi Ueda'
;Kitasato University
Japan
;
_audit_update_record             
;
2022-01-12 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_audit_creation_date             2022-01-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
3-butyl-2,4-dichloro-1,5-bis(methylsulfinyl)benzene
_chemical_formula_moiety         '2(C12 H16 Cl2 O2 S2)'
_chemical_formula_sum            'C24 H32 Cl4 O4 S4'
_chemical_formula_weight         654.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H16O2S2Cl2
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'
Cl Cl 0.3639 0.7018 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1703(2)
_cell_length_b                   14.5677(3)
_cell_length_c                   22.8030(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.171(2)
_cell_angle_gamma                90
_cell_volume                     3007.32(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12279
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      75.9850
_cell_measurement_theta_min      3.6690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.416
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
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    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.591
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21774
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.396
_diffrn_reflns_theta_min         3.614
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    105.00 141.00   0.50    0.38    --  105.24  93.00-120.00   72
  2  ω     92.00 123.00   0.50    0.38    --  105.24  15.00-180.00   62
  3  ω    129.00 166.00   0.50    0.38    --  105.24  15.00-180.00   74
  4  ω    -48.00 -20.00   0.50    0.38    --  -91.75  45.00  90.00   56
  5  ω    -51.00 -25.00   0.50    0.38    --  -91.75  45.00  60.00   52
  6  ω    -65.00 -40.00   0.50    0.38    --  -91.75  61.00  30.00   50
  7  ω    -47.00 -22.00   0.50    0.38    --  -91.75  45.00   0.00   50
  8  ω    -48.00 -22.00   0.50    0.38    --  -91.75  45.00 -30.00   52
  9  ω    -11.00  19.00   0.50    0.09    --  -47.20  19.00 -30.00   60
 10  ω    -49.00 -23.00   0.50    0.38    --  -91.75  45.00 -90.00   52
 11  ω    -51.00 -22.00   0.50    0.38    --  -91.75  45.00-180.00   58
 12  ω    -77.00  22.00   0.50    0.09    --  -47.20  93.00-120.00  198
 13  ω    -79.00 -22.00   0.50    0.38    --  -91.75  93.00-120.00  114
 14  ω    -83.00 -23.00   0.50    0.38    --  -91.75 125.00-120.00  120
 15  ω     31.00  75.00   0.50    0.09    --   47.20 -93.00 127.00   88
 16  ω     73.00 103.00   0.50    0.38    --  105.24 -93.00 127.00   60
 17  ω     43.00  68.00   0.50    0.38    --  105.24 -93.00 127.00   50
 18  ω     35.00  63.00   0.50    0.38    --  105.24 -61.00-180.00   56
 19  ω     34.00  77.00   0.50    0.38    --  105.24 -77.00-150.00   86
 20  ω     43.00 104.00   0.50    0.38    --  105.24 -77.00 -60.00  122
 21  ω     35.00  68.00   0.50    0.38    --  105.24 -61.00   0.00   66
 22  ω     38.00  70.00   0.50    0.38    --  105.24 -61.00  30.00   64
 23  ω     34.00  71.00   0.50    0.38    --  105.24 -61.00  60.00   74
 24  ω     37.00  98.00   0.50    0.38    --  105.24 -77.00 150.00  122
 25  ω    -22.00  27.00   0.50    0.09    --   47.20 -19.00  60.00   98
 26  ω   -116.00 -73.00   0.50    0.09    --  -47.20-125.00 -60.00   86
 27  ω   -119.00 -80.00   0.50    0.09    --  -47.20-125.00 -90.00   78
 28  ω   -132.00-106.00   0.50    0.38    --  -91.75 -93.00 127.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0625767000
_diffrn_orient_matrix_UB_12      -0.0977946000
_diffrn_orient_matrix_UB_13      -0.0027315000
_diffrn_orient_matrix_UB_21      0.0210052000
_diffrn_orient_matrix_UB_22      -0.0061587000
_diffrn_orient_matrix_UB_23      0.0682989000
_diffrn_orient_matrix_UB_31      -0.1567597000
_diffrn_orient_matrix_UB_32      -0.0398224000
_diffrn_orient_matrix_UB_33      -0.0038039000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5258
_reflns_number_total             5998
_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 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.782
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         5998
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0695
_refine_ls_restrained_S_all      1.054
_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)+(0.1484P)²+1.1653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1934
_refine_ls_wR_factor_ref         0.2002
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C8(H8A,H8B), C7(H7A,H7B), C21(H21A,H21B), C9(H9A,H9B),
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C23(H23A,H23B,
 H23C), C10(H10A,H10B,H10C), C22(H22A,H22B,H22C)
;
_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
S2 S 0.27663(8) 0.08589(5) 0.80599(3) 0.0263(2) Uani 1 1 d . . . . .
Cl1 Cl 0.42474(8) 0.06952(5) 0.54587(3) 0.0322(2) Uani 1 1 d . . . . .
S1 S 0.22772(8) 0.23027(5) 0.58296(3) 0.0269(2) Uani 1 1 d . . . . .
S4 S 0.76914(8) 0.63595(5) 0.79608(3) 0.0276(2) Uani 1 1 d . . . . .
Cl2 Cl 0.43672(8) -0.08891(5) 0.76174(4) 0.0329(2) Uani 1 1 d . . . . .
Cl4 Cl 0.93276(9) 0.81374(5) 0.75623(4) 0.0339(2) Uani 1 1 d . . . . .
S3 S 0.72506(8) 0.50222(5) 0.57110(4) 0.0300(2) Uani 1 1 d . . . . .
Cl3 Cl 0.93441(8) 0.66217(6) 0.53918(4) 0.0340(2) Uani 1 1 d . . . . .
O2 O 0.2096(3) 0.17894(15) 0.80854(11) 0.0322(5) Uani 1 1 d . . . . .
O4 O 0.7027(3) 0.54239(15) 0.79604(11) 0.0347(5) Uani 1 1 d . . . . .
O1 O 0.1278(3) 0.28620(17) 0.61439(13) 0.0414(6) Uani 1 1 d . . . . .
O3 O 0.6160(3) 0.45069(18) 0.59993(14) 0.0459(7) Uani 1 1 d . . . . .
C6 C 0.2716(3) 0.14654(19) 0.69283(14) 0.0228(6) Uani 1 1 d . . . . .
H6 H 0.220189 0.197492 0.705665 0.027 Uiso 1 1 calc R U . . .
C1 C 0.3049(3) 0.14392(19) 0.63522(14) 0.0229(6) Uani 1 1 d . . . . .
C18 C 0.8081(3) 0.6517(2) 0.72157(14) 0.0232(6) Uani 1 1 d . . . . .
C14 C 0.8008(3) 0.5878(2) 0.62463(14) 0.0245(6) Uani 1 1 d . . . . .
C5 C 0.3136(3) 0.07513(19) 0.73055(13) 0.0222(6) Uani 1 1 d . . . . .
C13 C 0.7652(3) 0.5825(2) 0.68108(14) 0.0245(6) Uani 1 1 d . . . . .
H13 H 0.711226 0.531348 0.692076 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3911(3) 0.00073(19) 0.71219(14) 0.0236(6) Uani 1 1 d . . . . .
C3 C 0.4305(3) -0.00409(19) 0.65552(14) 0.0238(6) Uani 1 1 d . . . . .
C17 C 0.8874(3) 0.7267(2) 0.70485(14) 0.0243(6) Uani 1 1 d . . . . .
C2 C 0.3832(3) 0.0693(2) 0.61779(13) 0.0226(6) Uani 1 1 d . . . . .
C15 C 0.8846(3) 0.6615(2) 0.60974(13) 0.0238(6) Uani 1 1 d . . . . .
C16 C 0.9300(3) 0.7337(2) 0.64905(15) 0.0260(6) Uani 1 1 d . . . . .
C20 C 0.9142(3) 0.8923(2) 0.60527(14) 0.0261(6) Uani 1 1 d . . . . .
H20A H 0.857649 0.871729 0.566894 0.031 Uiso 1 1 calc R U . . .
H20B H 0.842627 0.906243 0.632280 0.031 Uiso 1 1 calc R U . . .
C8 C 0.4140(3) -0.1577(2) 0.60366(15) 0.0258(6) Uani 1 1 d . . . . .
H8A H 0.346651 -0.180115 0.630411 0.031 Uiso 1 1 calc R U . . .
H8B H 0.352797 -0.130170 0.568364 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5154(3) -0.0836(2) 0.63595(15) 0.0271(6) Uani 1 1 d . . . . .
H7A H 0.577021 -0.111114 0.671150 0.033 Uiso 1 1 calc R U . . .
H7B H 0.582363 -0.060817 0.609137 0.033 Uiso 1 1 calc R U . . .
C21 C 0.9990(3) 0.9796(2) 0.59520(16) 0.0316(7) Uani 1 1 d . . . . .
H21A H 1.047914 1.003529 0.634043 0.038 Uiso 1 1 calc R U . . .
H21B H 1.077012 0.964506 0.571334 0.038 Uiso 1 1 calc R U . . .
C24 C 0.6197(4) 0.7160(2) 0.79211(16) 0.0347(7) Uani 1 1 d . . . . .
H24A H 0.544419 0.701150 0.757881 0.052 Uiso 1 1 calc R U . . .
H24B H 0.656706 0.778271 0.787675 0.052 Uiso 1 1 calc R U . . .
H24C H 0.576142 0.712249 0.828590 0.052 Uiso 1 1 calc R U . . .
C12 C 0.1277(4) 0.0050(2) 0.80144(16) 0.0333(7) Uani 1 1 d . . . . .
H12A H 0.081437 0.009571 0.837224 0.050 Uiso 1 1 calc R U . . .
H12B H 0.166069 -0.057308 0.798253 0.050 Uiso 1 1 calc R U . . .
H12C H 0.054220 0.018454 0.766368 0.050 Uiso 1 1 calc R U . . .
C9 C 0.4991(3) -0.2385(2) 0.58406(15) 0.0289(6) Uani 1 1 d . . . . .
H9A H 0.554769 -0.268944 0.619556 0.035 Uiso 1 1 calc R U . . .
H9B H 0.571463 -0.215757 0.559565 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3909(4) 0.2980(2) 0.58330(15) 0.0323(7) Uani 1 1 d . . . . .
H11A H 0.367734 0.351223 0.557193 0.048 Uiso 1 1 calc R U . . .
H11B H 0.467109 0.260778 0.569052 0.048 Uiso 1 1 calc R U . . .
H11C H 0.427063 0.319027 0.623825 0.048 Uiso 1 1 calc R U . . .
C19 C 1.0158(3) 0.8145(2) 0.63192(15) 0.0283(6) Uani 1 1 d . . . . .
H19A H 1.078185 0.794638 0.602617 0.034 Uiso 1 1 calc R U . . .
H19B H 1.081826 0.837477 0.667491 0.034 Uiso 1 1 calc R U . . .
C23 C 0.8854(4) 0.4299(2) 0.57729(17) 0.0359(8) Uani 1 1 d . . . . .
H23A H 0.910010 0.407320 0.618159 0.054 Uiso 1 1 calc R U . . .
H23B H 0.968708 0.465159 0.566995 0.054 Uiso 1 1 calc R U . . .
H23C H 0.864876 0.377708 0.550102 0.054 Uiso 1 1 calc R U . . .
C10 C 0.3979(4) -0.3086(2) 0.54830(16) 0.0360(7) Uani 1 1 d . . . . .
H10A H 0.348512 -0.280130 0.511488 0.054 Uiso 1 1 calc R U . . .
H10B H 0.323588 -0.329569 0.571776 0.054 Uiso 1 1 calc R U . . .
H10C H 0.456509 -0.361122 0.538652 0.054 Uiso 1 1 calc R U . . .
C22 C 0.8996(4) 1.0538(2) 0.56347(16) 0.0360(7) Uani 1 1 d . . . . .
H22A H 0.857822 1.032577 0.523545 0.054 Uiso 1 1 calc R U . . .
H22B H 0.957539 1.109698 0.560443 0.054 Uiso 1 1 calc R U . . .
H22C H 0.819505 1.067079 0.585959 0.054 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
S2 O2 1.493(2) . ?
S2 C5 1.812(3) . ?
S2 C12 1.795(3) . ?
Cl1 C2 1.742(3) . ?
S1 O1 1.492(2) . ?
S1 C1 1.798(3) . ?
S1 C11 1.791(3) . ?
S4 O4 1.493(2) . ?
S4 C18 1.806(3) . ?
S4 C24 1.790(3) . ?
Cl2 C4 1.734(3) . ?
Cl4 C17 1.732(3) . ?
S3 O3 1.485(3) . ?
S3 C14 1.804(3) . ?
S3 C23 1.796(3) . ?
Cl3 C15 1.741(3) . ?
C6 H6 0.9500 . ?
C6 C1 1.396(4) . ?
C6 C5 1.366(4) . ?
C1 C2 1.396(4) . ?
C18 C13 1.381(4) . ?
C18 C17 1.398(4) . ?
C14 C13 1.380(4) . ?
C14 C15 1.394(4) . ?
C5 C4 1.397(4) . ?
C13 H13 0.9500 . ?
C4 C3 1.398(5) . ?
C3 C2 1.397(4) . ?
C3 C7 1.502(4) . ?
C17 C16 1.393(5) . ?
C15 C16 1.401(4) . ?
C16 C19 1.501(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.527(4) . ?
C20 C19 1.530(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.535(4) . ?
C8 C9 1.519(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.521(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.526(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S2 C5 104.83(13) . . ?
O2 S2 C12 106.51(15) . . ?
C12 S2 C5 98.28(15) . . ?
O1 S1 C1 105.69(14) . . ?
O1 S1 C11 105.89(16) . . ?
C11 S1 C1 98.18(14) . . ?
O4 S4 C18 104.91(14) . . ?
O4 S4 C24 106.57(15) . . ?
C24 S4 C18 97.71(15) . . ?
O3 S3 C14 105.29(15) . . ?
O3 S3 C23 105.62(17) . . ?
C23 S3 C14 97.48(15) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C1 119.3(3) . . ?
C6 C1 S1 118.9(2) . . ?
C2 C1 S1 121.5(2) . . ?
C2 C1 C6 119.3(3) . . ?
C13 C18 S4 117.3(2) . . ?
C13 C18 C17 119.5(3) . . ?
C17 C18 S4 123.0(2) . . ?
C13 C14 S3 118.0(2) . . ?
C13 C14 C15 119.5(3) . . ?
C15 C14 S3 122.4(2) . . ?
C6 C5 S2 117.1(2) . . ?
C6 C5 C4 120.5(3) . . ?
C4 C5 S2 122.2(2) . . ?
C18 C13 H13 120.0 . . ?
C14 C13 C18 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C5 C4 Cl2 118.1(2) . . ?
C5 C4 C3 122.3(3) . . ?
C3 C4 Cl2 119.6(2) . . ?
C4 C3 C7 122.4(3) . . ?
C2 C3 C4 115.5(3) . . ?
C2 C3 C7 122.1(3) . . ?
C18 C17 Cl4 117.8(2) . . ?
C16 C17 Cl4 119.5(2) . . ?
C16 C17 C18 122.7(3) . . ?
C1 C2 Cl1 117.8(2) . . ?
C1 C2 C3 123.0(3) . . ?
C3 C2 Cl1 119.3(2) . . ?
C14 C15 Cl3 117.7(2) . . ?
C14 C15 C16 122.8(3) . . ?
C16 C15 Cl3 119.5(2) . . ?
C17 C16 C15 115.5(3) . . ?
C17 C16 C19 122.0(3) . . ?
C15 C16 C19 122.5(3) . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 H20A 109.1 . . ?
C21 C20 H20B 109.1 . . ?
C21 C20 C19 112.6(2) . . ?
C19 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C9 C8 C7 112.7(2) . . ?
C3 C7 C8 112.4(2) . . ?
C3 C7 H7A 109.1 . . ?
C3 C7 H7B 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 C20 112.5(3) . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
S4 C24 H24A 109.5 . . ?
S4 C24 H24B 109.5 . . ?
S4 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
S2 C12 H12A 109.5 . . ?
S2 C12 H12B 109.5 . . ?
S2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C8 C9 C10 112.2(3) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 C19 C20 111.9(2) . . ?
C16 C19 H19A 109.2 . . ?
C16 C19 H19B 109.2 . . ?
C20 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
S3 C23 H23A 109.5 . . ?
S3 C23 H23B 109.5 . . ?
S3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
S2 C5 C4 Cl2 6.4(3) . . . . ?
S2 C5 C4 C3 -174.6(2) . . . . ?
S1 C1 C2 Cl1 8.0(3) . . . . ?
S1 C1 C2 C3 -172.7(2) . . . . ?
S4 C18 C13 C14 -175.6(2) . . . . ?
S4 C18 C17 Cl4 -7.0(3) . . . . ?
S4 C18 C17 C16 173.3(2) . . . . ?
Cl2 C4 C3 C2 177.2(2) . . . . ?
Cl2 C4 C3 C7 -1.7(4) . . . . ?
Cl4 C17 C16 C15 -178.1(2) . . . . ?
Cl4 C17 C16 C19 0.5(4) . . . . ?
S3 C14 C13 C18 -173.3(2) . . . . ?
S3 C14 C15 Cl3 -7.7(3) . . . . ?
S3 C14 C15 C16 172.7(2) . . . . ?
Cl3 C15 C16 C17 -178.9(2) . . . . ?
Cl3 C15 C16 C19 2.5(4) . . . . ?
O2 S2 C5 C6 -2.3(3) . . . . ?
O2 S2 C5 C4 173.1(2) . . . . ?
O4 S4 C18 C13 3.3(3) . . . . ?
O4 S4 C18 C17 -172.2(2) . . . . ?
O1 S1 C1 C6 -4.4(3) . . . . ?
O1 S1 C1 C2 168.5(2) . . . . ?
O3 S3 C14 C13 8.9(3) . . . . ?
O3 S3 C14 C15 -166.6(2) . . . . ?
C6 C1 C2 Cl1 -179.1(2) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C6 C5 C4 Cl2 -178.3(2) . . . . ?
C6 C5 C4 C3 0.7(4) . . . . ?
C1 C6 C5 S2 176.5(2) . . . . ?
C1 C6 C5 C4 1.0(4) . . . . ?
C18 C17 C16 C15 1.7(4) . . . . ?
C18 C17 C16 C19 -179.7(3) . . . . ?
C14 C15 C16 C17 0.7(4) . . . . ?
C14 C15 C16 C19 -177.8(3) . . . . ?
C5 C6 C1 S1 171.7(2) . . . . ?
C5 C6 C1 C2 -1.4(4) . . . . ?
C5 C4 C3 C2 -1.8(4) . . . . ?
C5 C4 C3 C7 179.3(3) . . . . ?
C13 C18 C17 Cl4 177.7(2) . . . . ?
C13 C18 C17 C16 -2.1(4) . . . . ?
C13 C14 C15 Cl3 176.9(2) . . . . ?
C13 C14 C15 C16 -2.8(4) . . . . ?
C4 C3 C2 Cl1 -179.4(2) . . . . ?
C4 C3 C2 C1 1.4(4) . . . . ?
C4 C3 C7 C8 93.6(3) . . . . ?
C17 C18 C13 C14 0.0(4) . . . . ?
C17 C16 C19 C20 -88.4(4) . . . . ?
C2 C3 C7 C8 -85.3(3) . . . . ?
C15 C14 C13 C18 2.3(4) . . . . ?
C15 C16 C19 C20 90.1(3) . . . . ?
C7 C3 C2 Cl1 -0.4(4) . . . . ?
C7 C3 C2 C1 -179.7(3) . . . . ?
C7 C8 C9 C10 -176.0(3) . . . . ?
C21 C20 C19 C16 172.4(3) . . . . ?
C24 S4 C18 C13 -106.2(2) . . . . ?
C24 S4 C18 C17 78.3(3) . . . . ?
C12 S2 C5 C6 107.3(2) . . . . ?
C12 S2 C5 C4 -77.3(3) . . . . ?
C9 C8 C7 C3 -179.7(3) . . . . ?
C11 S1 C1 C6 104.7(2) . . . . ?
C11 S1 C1 C2 -82.4(3) . . . . ?
C19 C20 C21 C22 174.7(3) . . . . ?
C23 S3 C14 C13 -99.6(3) . . . . ?
C23 S3 C14 C15 84.9(3) . . . . ?

_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 2.000
_oxdiff_exptl_absorpt_empirical_full_min 0.431
####################################################################### 
# 
# 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_exp_1694_auto
_database_code_depnum_ccdc_archive 'CCDC 2153528'
loop_
_audit_author_name
_audit_author_address
'Masafumi Ueda'
;Kitasato University
Japan
;
_audit_update_record             
;
2022-02-21 deposited with the CCDC.	2022-03-28 downloaded from the CCDC.
;
_audit_creation_date             2022-02-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 S5, C6 H6'
_chemical_formula_sum            'C28 H22 S5'
_chemical_formula_weight         518.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         C50H38S10
_chemical_oxdiff_usercomment     'phenylene 2mer -100deg'
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6067(3)
_cell_length_b                   11.3115(2)
_cell_length_c                   11.6687(2)
_cell_angle_alpha                76.325(2)
_cell_angle_beta                 78.743(2)
_cell_angle_gamma                88.930(2)
_cell_volume                     1207.84(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6457
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      70.8950
_cell_measurement_theta_min      3.9760
_shelx_estimated_absorpt_T_max   0.588
_shelx_estimated_absorpt_T_min   0.196
_exptl_absorpt_coefficient_mu    4.534
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
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    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.131
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10752
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.050
_diffrn_reflns_theta_min         3.976
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  33.00   0.50    0.05    --    0.00  72.00-132.00   62
  2  ω     43.00  81.00   0.50    0.05    --    0.00  72.00-132.00   76
  3  ω     11.00 132.00   0.50    0.05    --   55.92  72.00-132.00  242
  4  ω     66.00 177.00   0.50    0.05    --  111.84  72.00-132.00  222
  5  ω     76.00 178.00   0.50    0.05    --  111.84   0.00-150.00  204
  6  ω     13.00  66.00   0.50    0.05    --  111.84   0.00-150.00  106
  7  ω      2.00  47.00   0.50    0.05    --    0.00 -99.00-150.00   90
  8  ω     36.00 104.00   0.50    0.05    --   55.92-125.00 -60.00  136
  9  ω     71.00 108.00   0.50    0.05    --  111.84-111.00 -90.00   74
 10  ω     60.00 108.00   0.50    0.05    --  111.84-111.00-180.00   96
 11  ω     77.00 108.00   0.50    0.05    --  111.84-111.00   0.00   62
 12  ω     34.00  93.00   0.50    0.05    --   55.92-125.00 120.00  118
 13  ω     75.00 107.00   0.50    0.05    --  111.84-111.00  90.00   64
 14  ω     38.00 101.00   0.50    0.05    --  111.84-111.00 150.00  126
 15  ω     24.00  65.00   0.50    0.05    --  111.84-111.00  90.00   82
 16  ω     37.00  63.00   0.50    0.05    --  111.84-111.00   0.00   52
 17  ω     35.00  61.00   0.50    0.05    --  111.84-111.00-120.00   52
 18  ω     27.00  53.00   0.50    0.05    --  111.84-111.00-180.00   52
 19  ω     19.00  44.00   0.50    0.05    --    0.00 -99.00 -60.00   50
 20  ω    -42.00  17.00   0.50    0.05    --   55.92 -15.00 -30.00  118
 21  ω    -17.00   9.00   0.50    0.05    --    0.00 -72.00  96.00   52
 22  ω     20.00  45.00   0.50    0.05    --    0.00 -72.00  96.00   50
 23  ω     33.00  90.00   0.50    0.05    --   55.92 -72.00  96.00  114
 24  ω     43.00  72.00   0.50    0.05    --  111.84 -63.00 150.00   58
 25  ω     57.00  83.00   0.50    0.05    --  111.84 -72.00  96.00   52
 26  ω     32.00  57.00   0.50    0.05    --  111.84 -50.00 -90.00   50
 27  ω     28.00  53.00   0.50    0.05    --  111.84 -50.00-120.00   50
 28  ω     27.00  53.00   0.50    0.05    --  111.84 -50.00-180.00   52
 29  ω     49.00  74.00   0.50    0.05    --  111.84 -63.00-150.00   50
 30  ω     31.00  57.00   0.50    0.05    --  111.84 -50.00  90.00   52
 31  ω     27.00  57.00   0.50    0.05    --  111.84 -50.00 120.00   60
 32  ω     27.00  52.00   0.50    0.05    --  111.84 -50.00 150.00   50
 33  ω    -33.00  18.00   0.50    0.05    --   55.92 -15.00 -90.00  102
 34  ω    -79.00 -36.00   0.50    0.05    -- -106.00  72.00-132.00   86
 35  ω    -56.00 -31.00   0.50    0.05    --  -55.92  72.00-132.00   50
 36  ω    -57.00 -32.00   0.50    0.05    -- -106.00  50.00   0.00   50
 37  ω    -53.00 -27.00   0.50    0.05    -- -106.00  50.00  60.00   52
 38  ω     -2.00  27.00   0.50    0.05    --  -55.92  45.00  30.00   58
 39  ω    -51.00 -25.00   0.50    0.05    --  -55.92  45.00  30.00   52
 40  ω    -22.00  18.00   0.50    0.05    --  -55.92  15.00 -30.00   80
 41  ω    -20.00   5.00   0.50    0.05    --  -55.92  15.00 -90.00   50
 42  ω    -13.00  24.00   0.50    0.05    --  -55.92  15.00-150.00   74
 43  ω    -24.00  14.00   0.50    0.05    --  -55.92  15.00-180.00   76
 44  ω    -63.00 -24.00   0.50    0.05    -- -106.00   0.00 -60.00   78
 45  ω   -176.00 -76.00   0.50    0.05    -- -106.00   0.00 -60.00  200
 46  ω    -80.00 -23.00   0.50    0.05    -- -106.00 111.00 -60.00  114
 47  ω    -62.00 -29.00   0.50    0.05    -- -106.00 111.00 -30.00   66
 48  ω    -80.00 -23.00   0.50    0.05    -- -106.00 111.00  30.00  114
 49  ω    -86.00 -25.00   0.50    0.05    --  -55.92 125.00 -90.00  122
 50  ω    -68.00 -23.00   0.50    0.05    -- -106.00 111.00-120.00   90
 51  ω   -127.00 -13.00   0.50    0.05    --  -55.92 -72.00  96.00  228
 52  ω   -112.00 -86.00   0.50    0.05    -- -106.00 -72.00  96.00   52
 53  ω   -155.00-125.00   0.50    0.05    -- -106.00 -72.00  96.00   60
 54  ω   -143.00 -88.00   0.50    0.05    --  -55.92-125.00 -90.00  110
 55  ω     92.00 144.00   0.50    0.05    --  111.84 178.00  30.00  104
 56  ω     63.00  88.00   0.50    0.05    --  111.84 178.00 120.00   50
 57  ω     94.00 142.00   0.50    0.05    --  111.84 178.00 120.00   96
 58  ω    111.00 137.00   0.50    0.05    --  111.84 178.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0251294000
_diffrn_orient_matrix_UB_12      -0.1048610000
_diffrn_orient_matrix_UB_13      0.1045391000
_diffrn_orient_matrix_UB_21      0.1614375000
_diffrn_orient_matrix_UB_22      0.0248504000
_diffrn_orient_matrix_UB_23      -0.0398082000
_diffrn_orient_matrix_UB_31      -0.0079743000
_diffrn_orient_matrix_UB_32      0.0897218000
_diffrn_orient_matrix_UB_33      0.0817932000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4392
_reflns_number_total             4499
_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 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4499
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.096
_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)+(0.0399P)²+1.0292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0942
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C7(H7), C13(H13), C16(H16), C17(H17), C24(H24),
 C25(H25), C23(H23), C28(H28), C27(H27), C26(H26)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
S4 S 0.44793(5) 0.57062(4) 0.87542(4) 0.01528(12) Uani 1 1 d . . . . .
S5 S 0.13686(5) 1.02485(5) 0.07437(5) 0.01674(13) Uani 1 1 d . . . . .
S2 S 0.15334(5) 0.57635(4) 0.51492(4) 0.01469(12) Uani 1 1 d . . . . .
S3 S 0.72939(5) 0.65450(5) 0.67584(4) 0.01637(13) Uani 1 1 d . . . . .
S1 S 0.43624(5) 0.67418(5) 0.32142(4) 0.01439(12) Uani 1 1 d . . . . .
C12 C 0.5634(2) 0.64311(18) 0.63459(18) 0.0140(4) Uani 1 1 d . . . . .
C6 C 0.2749(2) 0.75000(18) 0.31257(18) 0.0126(4) Uani 1 1 d . . . . .
C11 C 0.4404(2) 0.60425(17) 0.72079(18) 0.0126(4) Uani 1 1 d . . . . .
C15 C 0.5586(2) 0.69068(18) 0.88203(18) 0.0138(4) Uani 1 1 d . . . . .
C5 C 0.1505(2) 0.70603(18) 0.39562(18) 0.0130(4) Uani 1 1 d . . . . .
C1 C 0.2708(2) 0.84979(18) 0.21775(18) 0.0142(4) Uani 1 1 d . . . . .
H1 H 0.355939 0.881409 0.163164 0.017 Uiso 1 1 calc R U . . .
C8 C 0.4335(2) 0.64867(18) 0.47721(18) 0.0126(4) Uani 1 1 d . . . . .
C14 C 0.6804(2) 0.72922(18) 0.79438(18) 0.0142(4) Uani 1 1 d . . . . .
C9 C 0.3110(2) 0.60630(18) 0.56267(18) 0.0126(4) Uani 1 1 d . . . . .
C10 C 0.3110(2) 0.58616(18) 0.68635(18) 0.0134(4) Uani 1 1 d . . . . .
C2 C 0.1419(2) 0.90376(18) 0.20241(18) 0.0140(4) Uani 1 1 d . . . . .
C3 C 0.0181(2) 0.86019(19) 0.28459(19) 0.0165(4) Uani 1 1 d . . . . .
H3 H -0.069860 0.896777 0.274253 0.020 Uiso 1 1 calc R U . . .
C19 C 0.1797(2) 0.53848(18) 0.77941(18) 0.0144(4) Uani 1 1 d . . . . .
H19A H 0.094769 0.572347 0.748459 0.017 Uiso 1 1 calc R U . . .
H19B H 0.182139 0.566625 0.853147 0.017 Uiso 1 1 calc R U . . .
C4 C 0.0232(2) 0.76258(19) 0.38234(18) 0.0152(4) Uani 1 1 d . . . . .
H4 H -0.060899 0.734681 0.440088 0.018 Uiso 1 1 calc R U . . .
C7 C 0.5591(2) 0.66897(18) 0.51292(18) 0.0145(4) Uani 1 1 d . . . . .
H7 H 0.641466 0.700333 0.454465 0.017 Uiso 1 1 calc R U . . .
C20 C 0.1670(2) 0.39883(19) 0.81130(19) 0.0171(4) Uani 1 1 d . . . . .
H20A H 0.154441 0.371552 0.739249 0.021 Uiso 1 1 calc R U . . .
H20B H 0.256665 0.365349 0.833326 0.021 Uiso 1 1 calc R U . . .
C13 C 0.7697(2) 0.81953(19) 0.80474(19) 0.0158(4) Uani 1 1 d . . . . .
H13 H 0.850525 0.847744 0.743242 0.019 Uiso 1 1 calc R U . . .
C18 C 0.7409(2) 0.86898(18) 0.90560(19) 0.0150(4) Uani 1 1 d . . . . .
C16 C 0.5281(2) 0.74264(19) 0.98082(19) 0.0168(4) Uani 1 1 d . . . . .
H16 H 0.443995 0.718638 1.039716 0.020 Uiso 1 1 calc R U . . .
C17 C 0.6210(2) 0.82974(19) 0.99323(19) 0.0164(4) Uani 1 1 d . . . . .
H17 H 0.601962 0.862460 1.062376 0.020 Uiso 1 1 calc R U . . .
C21 C 0.0438(2) 0.3470(2) 0.9147(2) 0.0209(5) Uani 1 1 d . . . . .
H21A H 0.043514 0.257092 0.930552 0.025 Uiso 1 1 calc R U . . .
H21B H 0.059756 0.369870 0.988039 0.025 Uiso 1 1 calc R U . . .
C22 C -0.1010(2) 0.3906(2) 0.8911(2) 0.0233(5) Uani 1 1 d . . . . .
H22A H -0.112962 0.377725 0.813381 0.035 Uiso 1 1 calc R U . . .
H22B H -0.107836 0.477489 0.889617 0.035 Uiso 1 1 calc R U . . .
H22C H -0.175428 0.344706 0.955038 0.035 Uiso 1 1 calc R U . . .
C24 C 0.2166(3) 0.9508(2) 0.5371(2) 0.0309(6) Uani 1 1 d . . . . .
H24 H 0.189780 0.956970 0.461795 0.037 Uiso 1 1 calc R U . . .
C25 C 0.1506(3) 0.8652(2) 0.6369(3) 0.0337(6) Uani 1 1 d . . . . .
H25 H 0.078385 0.812367 0.630337 0.040 Uiso 1 1 calc R U . . .
C23 C 0.3215(3) 1.0278(2) 0.5463(3) 0.0346(6) Uani 1 1 d . . . . .
H23 H 0.366416 1.087157 0.477454 0.042 Uiso 1 1 calc R U . . .
C28 C 0.3614(3) 1.0185(3) 0.6556(3) 0.0408(7) Uani 1 1 d . . . . .
H28 H 0.433899 1.071306 0.661792 0.049 Uiso 1 1 calc R U . . .
C27 C 0.2955(4) 0.9321(3) 0.7566(3) 0.0431(7) Uani 1 1 d . . . . .
H27 H 0.322777 0.925195 0.831799 0.052 Uiso 1 1 calc R U . . .
C26 C 0.1894(4) 0.8560(2) 0.7463(3) 0.0417(7) Uani 1 1 d . . . . .
H26 H 0.143158 0.797208 0.815001 0.050 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
S4 C11 1.770(2) . ?
S4 C15 1.765(2) . ?
S5 C2 1.780(2) . ?
S5 C18 1.780(2) 2_676 ?
S2 C5 1.772(2) . ?
S2 C9 1.777(2) . ?
S3 C12 1.769(2) . ?
S3 C14 1.770(2) . ?
S1 C6 1.766(2) . ?
S1 C8 1.767(2) . ?
C12 C11 1.395(3) . ?
C12 C7 1.389(3) . ?
C6 C5 1.399(3) . ?
C6 C1 1.387(3) . ?
C11 C10 1.411(3) . ?
C15 C14 1.396(3) . ?
C15 C16 1.394(3) . ?
C5 C4 1.388(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.394(3) . ?
C8 C9 1.395(3) . ?
C8 C7 1.391(3) . ?
C14 C13 1.388(3) . ?
C9 C10 1.407(3) . ?
C10 C19 1.508(3) . ?
C2 C3 1.390(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.536(3) . ?
C4 H4 0.9500 . ?
C7 H7 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.527(3) . ?
C13 H13 0.9500 . ?
C13 C18 1.398(3) . ?
C18 C17 1.383(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(3) . ?
C17 H17 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.521(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24 0.9500 . ?
C24 C25 1.378(4) . ?
C24 C23 1.380(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.378(4) . ?
C23 H23 0.9500 . ?
C23 C28 1.382(4) . ?
C28 H28 0.9500 . ?
C28 C27 1.390(5) . ?
C27 H27 0.9500 . ?
C27 C26 1.387(5) . ?
C26 H26 0.9500 . ?

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
C15 S4 C11 101.86(9) . . ?
C18 S5 C2 100.45(9) 2_676 . ?
C5 S2 C9 101.21(9) . . ?
C12 S3 C14 100.55(9) . . ?
C6 S1 C8 100.35(9) . . ?
C11 C12 S3 121.51(15) . . ?
C7 C12 S3 118.13(16) . . ?
C7 C12 C11 120.30(18) . . ?
C5 C6 S1 120.69(15) . . ?
C1 C6 S1 119.18(15) . . ?
C1 C6 C5 120.02(18) . . ?
C12 C11 S4 119.72(15) . . ?
C12 C11 C10 120.88(18) . . ?
C10 C11 S4 119.34(15) . . ?
C14 C15 S4 121.33(16) . . ?
C16 C15 S4 119.10(16) . . ?
C16 C15 C14 119.44(19) . . ?
C6 C5 S2 120.51(15) . . ?
C4 C5 S2 119.82(16) . . ?
C4 C5 C6 119.65(19) . . ?
C6 C1 H1 119.9 . . ?
C6 C1 C2 120.14(19) . . ?
C2 C1 H1 119.9 . . ?
C9 C8 S1 121.61(15) . . ?
C7 C8 S1 117.89(15) . . ?
C7 C8 C9 120.48(18) . . ?
C15 C14 S3 119.97(16) . . ?
C13 C14 S3 119.52(16) . . ?
C13 C14 C15 120.31(19) . . ?
C8 C9 S2 119.66(15) . . ?
C8 C9 C10 120.81(18) . . ?
C10 C9 S2 119.53(15) . . ?
C11 C10 C19 120.92(18) . . ?
C9 C10 C11 117.80(18) . . ?
C9 C10 C19 121.15(18) . . ?
C1 C2 S5 119.46(16) . . ?
C3 C2 S5 120.56(16) . . ?
C3 C2 C1 119.95(19) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.84(19) . . ?
C4 C3 H3 120.1 . . ?
C10 C19 H19A 109.2 . . ?
C10 C19 H19B 109.2 . . ?
C10 C19 C20 112.26(17) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
C5 C4 C3 120.33(19) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C12 C7 C8 119.58(19) . . ?
C12 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C19 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 C19 113.57(18) . . ?
C21 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C18 120.02(19) . . ?
C18 C13 H13 120.0 . . ?
C13 C18 S5 120.16(16) . 2_676 ?
C17 C18 S5 120.08(16) . 2_676 ?
C17 C18 C13 119.66(19) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.02(19) . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.48(19) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 C20 113.97(18) . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C25 C24 H24 119.9 . . ?
C25 C24 C23 120.2(3) . . ?
C23 C24 H24 119.9 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.1(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C23 H23 120.0 . . ?
C24 C23 C28 120.0(3) . . ?
C28 C23 H23 120.0 . . ?
C23 C28 H28 120.0 . . ?
C23 C28 C27 120.1(3) . . ?
C27 C28 H28 120.0 . . ?
C28 C27 H27 120.4 . . ?
C26 C27 C28 119.3(3) . . ?
C26 C27 H27 120.4 . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?

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
S4 C11 C10 C9 -175.98(14) . . . . ?
S4 C11 C10 C19 -0.1(3) . . . . ?
S4 C15 C14 S3 -1.8(2) . . . . ?
S4 C15 C14 C13 -176.66(15) . . . . ?
S4 C15 C16 C17 174.19(16) . . . . ?
S5 C2 C3 C4 177.88(15) . . . . ?
S5 C18 C17 C16 -177.12(16) 2_676 . . . ?
S2 C5 C4 C3 -176.10(15) . . . . ?
S2 C9 C10 C11 176.39(14) . . . . ?
S2 C9 C10 C19 0.5(3) . . . . ?
S3 C12 C11 S4 2.4(2) . . . . ?
S3 C12 C11 C10 -174.83(15) . . . . ?
S3 C12 C7 C8 173.28(15) . . . . ?
S3 C14 C13 C18 -172.38(15) . . . . ?
S1 C6 C5 S2 2.3(2) . . . . ?
S1 C6 C5 C4 -175.90(15) . . . . ?
S1 C6 C1 C2 173.78(15) . . . . ?
S1 C8 C9 S2 0.2(2) . . . . ?
S1 C8 C9 C10 179.80(15) . . . . ?
S1 C8 C7 C12 -176.23(15) . . . . ?
C12 S3 C14 C15 45.14(18) . . . . ?
C12 S3 C14 C13 -139.95(17) . . . . ?
C12 C11 C10 C9 1.2(3) . . . . ?
C12 C11 C10 C19 177.09(18) . . . . ?
C6 S1 C8 C9 44.49(18) . . . . ?
C6 S1 C8 C7 -137.25(16) . . . . ?
C6 C5 C4 C3 2.1(3) . . . . ?
C6 C1 C2 S5 -175.62(15) . . . . ?
C6 C1 C2 C3 2.2(3) . . . . ?
C11 S4 C15 C14 -42.49(19) . . . . ?
C11 S4 C15 C16 141.57(17) . . . . ?
C11 C12 C7 C8 -4.0(3) . . . . ?
C11 C10 C19 C20 -89.7(2) . . . . ?
C15 S4 C11 C12 41.86(18) . . . . ?
C15 S4 C11 C10 -140.92(16) . . . . ?
C15 C14 C13 C18 2.5(3) . . . . ?
C15 C16 C17 C18 2.6(3) . . . . ?
C5 S2 C9 C8 -44.18(18) . . . . ?
C5 S2 C9 C10 136.25(16) . . . . ?
C5 C6 C1 C2 -2.3(3) . . . . ?
C1 C6 C5 S2 178.39(15) . . . . ?
C1 C6 C5 C4 0.2(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C8 S1 C6 C5 -45.72(18) . . . . ?
C8 S1 C6 C1 138.20(16) . . . . ?
C8 C9 C10 C11 -3.2(3) . . . . ?
C8 C9 C10 C19 -179.03(18) . . . . ?
C14 S3 C12 C11 -45.81(18) . . . . ?
C14 S3 C12 C7 136.94(16) . . . . ?
C14 C15 C16 C17 -1.8(3) . . . . ?
C14 C13 C18 S5 174.55(15) . . . 2_676 ?
C14 C13 C18 C17 -1.7(3) . . . . ?
C9 S2 C5 C6 42.93(18) . . . . ?
C9 S2 C5 C4 -138.83(16) . . . . ?
C9 C8 C7 C12 2.0(3) . . . . ?
C9 C10 C19 C20 86.0(2) . . . . ?
C10 C19 C20 C21 173.89(17) . . . . ?
C2 C3 C4 C5 -2.3(3) . . . . ?
C19 C20 C21 C22 59.3(2) . . . . ?
C7 C12 C11 S4 179.54(15) . . . . ?
C7 C12 C11 C10 2.4(3) . . . . ?
C7 C8 C9 S2 -177.97(15) . . . . ?
C7 C8 C9 C10 1.6(3) . . . . ?
C13 C18 C17 C16 -0.9(3) . . . . ?
C18 S5 C2 C1 -58.42(18) 2_676 . . . ?
C18 S5 C2 C3 123.75(17) 2_676 . . . ?
C16 C15 C14 S3 174.13(15) . . . . ?
C16 C15 C14 C13 -0.7(3) . . . . ?
C24 C25 C26 C27 -0.5(4) . . . . ?
C24 C23 C28 C27 -0.3(4) . . . . ?
C25 C24 C23 C28 0.4(4) . . . . ?
C23 C24 C25 C26 -0.1(4) . . . . ?
C23 C28 C27 C26 -0.3(4) . . . . ?
C28 C27 C26 C25 0.6(4) . . . . ?

_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 1.751
_oxdiff_exptl_absorpt_empirical_full_min 0.604
