# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_mj20384_0m
_database_code_depnum_ccdc_archive 'CCDC 2091455'
loop_
_audit_author_name
_audit_author_address
'Xuebing Leng'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2021-06-22 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_audit_creation_date             2020-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 O S2'
_chemical_formula_sum            'C20 H20 O S2'
_chemical_formula_weight         340.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 '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                   9.8031(5)
_cell_length_b                   12.4858(6)
_cell_length_c                   14.4741(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.794(2)
_cell_angle_gamma                90
_cell_volume                     1740.28(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.96
_cell_measurement_theta_min      3.99
_shelx_estimated_absorpt_T_max   0.915
_shelx_estimated_absorpt_T_min   0.869
_exptl_absorpt_coefficient_mu    1.803
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1260 before and 0.0579 after correction. The Ratio of minimum to maximum transmission is 0.7170. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19615
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.954
_diffrn_reflns_theta_min         3.994
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3161
_reflns_number_total             3294
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.889
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+1.4247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1107
_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:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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
S1 S 0.42835(5) 0.34995(4) 0.42476(4) 0.03286(15) Uani 1 1 d . . . . .
S2 S 0.57174(5) 0.41809(4) 0.35963(3) 0.03627(16) Uani 1 1 d . . . . .
O1 O 0.66591(15) 0.16531(12) 0.39360(11) 0.0407(4) Uani 1 1 d . . . . .
C1 C 0.42851(19) 0.20071(15) 0.40024(13) 0.0286(4) Uani 1 1 d . . . . .
C2 C 0.57640(19) 0.16679(15) 0.44194(14) 0.0290(4) Uani 1 1 d . . . . .
C3 C 0.61105(19) 0.14080(15) 0.54353(14) 0.0289(4) Uani 1 1 d . . . . .
C4 C 0.50782(19) 0.12534(16) 0.59094(13) 0.0303(4) Uani 1 1 d . . . . .
H4 H 0.531771 0.108278 0.655925 0.036 Uiso 1 1 calc R . . . .
C5 C 0.36166(19) 0.13304(15) 0.54917(13) 0.0274(4) Uani 1 1 d . . . . .
C6 C 0.2614(2) 0.10561(16) 0.60215(14) 0.0322(4) Uani 1 1 d . . . . .
H6 H 0.289789 0.084218 0.665839 0.039 Uiso 1 1 calc R . . . .
C7 C 0.1223(2) 0.10913(16) 0.56344(16) 0.0356(5) Uani 1 1 d . . . . .
H7 H 0.055283 0.089511 0.600017 0.043 Uiso 1 1 calc R . . . .
C8 C 0.0804(2) 0.14122(16) 0.47138(16) 0.0369(5) Uani 1 1 d . . . . .
H8 H -0.015758 0.144252 0.444645 0.044 Uiso 1 1 calc R . . . .
C9 C 0.1784(2) 0.16915(16) 0.41757(15) 0.0342(4) Uani 1 1 d . . . . .
H9 H 0.148459 0.191362 0.354241 0.041 Uiso 1 1 calc R . . . .
C10 C 0.31966(19) 0.16504(14) 0.45518(13) 0.0267(4) Uani 1 1 d . . . . .
C11 C 0.3950(3) 0.17974(19) 0.29540(14) 0.0426(5) Uani 1 1 d . . . . .
H11A H 0.307672 0.215408 0.268196 0.064 Uiso 1 1 calc GR . . . .
H11B H 0.385717 0.102463 0.284112 0.064 Uiso 1 1 calc GR . . . .
H11C H 0.470006 0.207776 0.266047 0.064 Uiso 1 1 calc GR . . . .
C12 C 0.7295(2) 0.42602(17) 0.45022(14) 0.0347(4) Uani 1 1 d . . . . .
H12A H 0.713536 0.472432 0.502631 0.042 Uiso 1 1 calc R . . . .
H12B H 0.756390 0.353847 0.475590 0.042 Uiso 1 1 calc R . . . .
C13 C 0.8421(2) 0.47236(16) 0.40436(13) 0.0299(4) Uani 1 1 d . . . . .
C14 C 0.8632(2) 0.58176(16) 0.40134(14) 0.0324(4) Uani 1 1 d . . . . .
H14 H 0.804640 0.629013 0.427502 0.039 Uiso 1 1 calc R . . . .
C15 C 0.9691(2) 0.62307(16) 0.36046(14) 0.0326(4) Uani 1 1 d . . . . .
H15 H 0.981728 0.698449 0.359073 0.039 Uiso 1 1 calc R . . . .
C16 C 1.0568(2) 0.55682(17) 0.32155(13) 0.0322(4) Uani 1 1 d . . . . .
C17 C 1.0337(2) 0.44729(18) 0.32318(15) 0.0394(5) Uani 1 1 d . . . . .
H17 H 1.091409 0.400147 0.296110 0.047 Uiso 1 1 calc R . . . .
C18 C 0.9279(2) 0.40556(17) 0.36368(16) 0.0386(5) Uani 1 1 d . . . . .
H18 H 0.913729 0.330295 0.363671 0.046 Uiso 1 1 calc R . . . .
C19 C 1.1747(2) 0.6022(2) 0.27999(16) 0.0439(5) Uani 1 1 d . . . . .
H19A H 1.173046 0.680563 0.283366 0.066 Uiso 1 1 calc GR . . . .
H19B H 1.164420 0.579838 0.214138 0.066 Uiso 1 1 calc GR . . . .
H19C H 1.263298 0.575637 0.315472 0.066 Uiso 1 1 calc GR . . . .
C20 C 0.7608(2) 0.12476(18) 0.58535(17) 0.0390(5) Uani 1 1 d . . . . .
H20A H 0.797481 0.064548 0.554048 0.059 Uiso 1 1 calc GR . . . .
H20B H 0.770434 0.109326 0.652641 0.059 Uiso 1 1 calc GR . . . .
H20C H 0.812891 0.189872 0.576791 0.059 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 S2 2.0211(7) . ?
S1 C1 1.897(2) . ?
S2 C12 1.833(2) . ?
O1 C2 1.221(2) . ?
C1 C2 1.522(3) . ?
C1 C10 1.512(3) . ?
C1 C11 1.514(3) . ?
C2 C3 1.482(3) . ?
C3 C4 1.339(3) . ?
C3 C20 1.493(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.450(3) . ?
C5 C6 1.398(3) . ?
C5 C10 1.404(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.374(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.391(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.506(3) . ?
C13 C14 1.383(3) . ?
C13 C18 1.391(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.387(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 C17 1.387(3) . ?
C16 C19 1.510(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C1 S1 S2 107.53(6) . . ?
C12 S2 S1 104.84(7) . . ?
C2 C1 S1 103.48(12) . . ?
C10 C1 S1 99.52(12) . . ?
C10 C1 C2 115.02(16) . . ?
C10 C1 C11 115.73(17) . . ?
C11 C1 S1 110.47(14) . . ?
C11 C1 C2 111.16(17) . . ?
O1 C2 C1 120.69(18) . . ?
O1 C2 C3 120.65(18) . . ?
C3 C2 C1 118.60(15) . . ?
C2 C3 C20 117.18(17) . . ?
C4 C3 C2 119.04(17) . . ?
C4 C3 C20 123.59(19) . . ?
C3 C4 H4 118.0 . . ?
C3 C4 C5 124.02(18) . . ?
C5 C4 H4 118.0 . . ?
C6 C5 C4 119.76(17) . . ?
C6 C5 C10 119.52(17) . . ?
C10 C5 C4 120.70(17) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.95(19) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.81(18) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.15(18) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.91(19) . . ?
C10 C9 H9 119.5 . . ?
C5 C10 C1 119.06(16) . . ?
C9 C10 C1 122.16(17) . . ?
C9 C10 C5 118.66(17) . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
S2 C12 H12A 110.3 . . ?
S2 C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 S2 107.17(13) . . ?
C13 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
C14 C13 C12 121.30(18) . . ?
C14 C13 C18 118.22(18) . . ?
C18 C13 C12 120.49(18) . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.60(18) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.48(19) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C17 117.74(18) . . ?
C15 C16 C19 121.17(19) . . ?
C17 C16 C19 121.09(19) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.03(19) . . ?
C18 C17 H17 119.5 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 120.91(19) . . ?
C17 C18 H18 119.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
C3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mj20395_0m
_database_code_depnum_ccdc_archive 'CCDC 2091456'
loop_
_audit_author_name
_audit_author_address
'Xuebing Leng'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2021-06-22 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_audit_creation_date             2020-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N O S2'
_chemical_formula_sum            'C20 H19 N O S2'
_chemical_formula_weight         353.48
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 '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                   9.8601(3)
_cell_length_b                   11.9035(3)
_cell_length_c                   15.2689(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.4180(10)
_cell_angle_gamma                90
_cell_volume                     1756.64(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.99
_cell_measurement_theta_min      3.98
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.869
_exptl_absorpt_coefficient_mu    1.811
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1163 before and 0.0651 after correction. The Ratio of minimum to maximum transmission is 0.7283. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15677
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.961
_diffrn_reflns_theta_min         3.979
_diffrn_ambient_temperature      173.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3181
_reflns_number_total             3317
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+0.8314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0937
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C15(H15), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
S1 S 0.34291(4) 0.62177(4) 0.70606(2) 0.02772(13) Uani 1 1 d . . . . .
S2 S 0.49876(4) 0.66974(3) 0.64565(3) 0.02780(13) Uani 1 1 d . . . . .
O1 O 0.10810(12) 0.51866(12) 0.74377(8) 0.0367(3) Uani 1 1 d . . . . .
H1 H 0.034381 0.498287 0.758772 0.055 Uiso 1 1 calc GR . . . .
N1 N 0.89849(18) 1.00911(16) 0.35327(12) 0.0476(4) Uani 1 1 d . . . . .
C1 C 0.08101(16) 0.54520(14) 0.65088(10) 0.0266(3) Uani 1 1 d . . . . .
H1A H 0.017260 0.486564 0.618833 0.032 Uiso 1 1 calc R . . . .
C2 C 0.22022(16) 0.53466(13) 0.62063(10) 0.0249(3) Uani 1 1 d . . . . .
C3 C 0.21058(16) 0.58284(14) 0.52773(10) 0.0266(3) Uani 1 1 d . . . . .
C4 C 0.28870(17) 0.54070(15) 0.46880(11) 0.0319(4) Uani 1 1 d . . . . .
H4 H 0.349179 0.479073 0.486408 0.038 Uiso 1 1 calc R . . . .
C5 C 0.27958(19) 0.58757(17) 0.38420(11) 0.0366(4) Uani 1 1 d . . . . .
H5 H 0.332145 0.556588 0.344225 0.044 Uiso 1 1 calc R . . . .
C6 C 0.19499(19) 0.67838(16) 0.35823(11) 0.0374(4) Uani 1 1 d . . . . .
H6 H 0.189900 0.710860 0.300840 0.045 Uiso 1 1 calc R . . . .
C7 C 0.11717(19) 0.72216(15) 0.41651(11) 0.0342(4) Uani 1 1 d . . . . .
H7 H 0.059674 0.785565 0.398977 0.041 Uiso 1 1 calc R . . . .
C8 C 0.12215(17) 0.67405(13) 0.50116(11) 0.0286(4) Uani 1 1 d . . . . .
C9 C 0.03291(17) 0.71555(14) 0.55972(11) 0.0312(4) Uani 1 1 d . . . . .
H9 H -0.011874 0.785966 0.546661 0.037 Uiso 1 1 calc R . . . .
C10 C 0.01198(16) 0.65833(14) 0.63076(11) 0.0282(3) Uani 1 1 d . . . . .
C11 C -0.09013(19) 0.69508(17) 0.68582(12) 0.0386(4) Uani 1 1 d . . . . .
H11A H -0.163058 0.638340 0.682135 0.058 Uiso 1 1 calc GR . . . .
H11B H -0.131295 0.766918 0.663105 0.058 Uiso 1 1 calc GR . . . .
H11C H -0.042810 0.704022 0.748199 0.058 Uiso 1 1 calc GR . . . .
C12 C 0.26987(18) 0.41349(14) 0.62901(12) 0.0328(4) Uani 1 1 d . . . . .
H12A H 0.366784 0.410222 0.622687 0.049 Uiso 1 1 calc GR . . . .
H12B H 0.213067 0.368118 0.582051 0.049 Uiso 1 1 calc GR . . . .
H12C H 0.261772 0.384017 0.687681 0.049 Uiso 1 1 calc GR . . . .
C13 C 0.44301(18) 0.80973(15) 0.60243(13) 0.0341(4) Uani 1 1 d . . . . .
H13A H 0.349638 0.805224 0.564058 0.041 Uiso 1 1 calc R . . . .
H13B H 0.438684 0.861353 0.652636 0.041 Uiso 1 1 calc R . . . .
C14 C 0.54472(16) 0.85321(14) 0.54920(11) 0.0273(3) Uani 1 1 d . . . . .
C15 C 0.64958(17) 0.92608(14) 0.58733(11) 0.0296(4) Uani 1 1 d . . . . .
H15 H 0.657659 0.948214 0.647918 0.035 Uiso 1 1 calc R . . . .
C16 C 0.74264(17) 0.96695(14) 0.53813(11) 0.0300(4) Uani 1 1 d . . . . .
H16 H 0.814262 1.016864 0.564646 0.036 Uiso 1 1 calc R . . . .
C17 C 0.73015(16) 0.93412(13) 0.44936(11) 0.0268(3) Uani 1 1 d . . . . .
C18 C 0.62600(18) 0.86061(15) 0.41041(11) 0.0331(4) Uani 1 1 d . . . . .
H18 H 0.617983 0.838246 0.349875 0.040 Uiso 1 1 calc R . . . .
C19 C 0.53436(18) 0.82042(15) 0.46050(12) 0.0343(4) Uani 1 1 d . . . . .
H19 H 0.463386 0.769806 0.434226 0.041 Uiso 1 1 calc R . . . .
C20 C 0.82492(18) 0.97634(15) 0.39633(12) 0.0345(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 S2 2.0246(5) . ?
S1 C2 1.9014(16) . ?
S2 C13 1.8360(17) . ?
O1 H1 0.8400 . ?
O1 C1 1.4258(19) . ?
N1 C20 1.140(2) . ?
C1 H1A 1.0000 . ?
C1 C2 1.538(2) . ?
C1 C10 1.513(2) . ?
C2 C3 1.515(2) . ?
C2 C12 1.520(2) . ?
C3 C4 1.389(2) . ?
C3 C8 1.401(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.406(2) . ?
C8 C9 1.459(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.331(2) . ?
C10 C11 1.499(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.502(2) . ?
C14 C15 1.386(2) . ?
C14 C19 1.394(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(2) . ?
C17 C18 1.390(2) . ?
C17 C20 1.443(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(3) . ?
C19 H19 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
C2 S1 S2 106.17(5) . . ?
C13 S2 S1 102.68(6) . . ?
C1 O1 H1 109.5 . . ?
O1 C1 H1A 107.9 . . ?
O1 C1 C2 106.15(12) . . ?
O1 C1 C10 112.80(13) . . ?
C2 C1 H1A 107.9 . . ?
C10 C1 H1A 107.9 . . ?
C10 C1 C2 113.84(13) . . ?
C1 C2 S1 103.53(10) . . ?
C3 C2 S1 110.44(11) . . ?
C3 C2 C1 110.86(13) . . ?
C3 C2 C12 113.41(13) . . ?
C12 C2 S1 108.00(11) . . ?
C12 C2 C1 110.11(13) . . ?
C4 C3 C2 121.98(15) . . ?
C4 C3 C8 119.04(15) . . ?
C8 C3 C2 118.97(14) . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.91(17) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.41(17) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.45(16) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 120.93(17) . . ?
C8 C7 H7 119.5 . . ?
C3 C8 C7 119.23(16) . . ?
C3 C8 C9 120.07(15) . . ?
C7 C8 C9 120.66(16) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 C8 122.39(16) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 C1 119.01(15) . . ?
C9 C10 C11 122.51(16) . . ?
C11 C10 C1 118.11(15) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S2 C13 H13A 109.9 . . ?
S2 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C14 C13 S2 108.83(11) . . ?
C14 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
C15 C14 C13 120.71(15) . . ?
C15 C14 C19 119.24(15) . . ?
C19 C14 C13 120.05(15) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.76(15) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.29(15) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C20 120.42(15) . . ?
C18 C17 C16 120.57(15) . . ?
C18 C17 C20 119.01(15) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.37(15) . . ?
C19 C18 H18 120.3 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.76(16) . . ?
C18 C19 H19 119.6 . . ?
N1 C20 C17 178.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
