# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

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

data_132741_0m_pl
_database_code_depnum_ccdc_archive 'CCDC 2004076'
loop_
_audit_author_name
_audit_author_address
'Chien-Fu Liang'
;National Chung Hsing University, Department of Chemistry
Taiwan
;
_audit_update_record             
;
2020-10-13 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_audit_creation_date             2019-06-28
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 N O2 S2'
_chemical_formula_sum            'C22 H21 N O2 S2'
_chemical_formula_weight         395.52
_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 0.0033 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.0525(5)
_cell_length_b                   15.8806(10)
_cell_length_c                   15.2504(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.189(2)
_cell_angle_gamma                90
_cell_volume                     1945.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.383
_cell_measurement_theta_min      3.062
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0793 before and 0.0392 after correction.
The Ratio of minimum to maximum transmission is 0.9153.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29071
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         2.894
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3597
_reflns_number_total             3899
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.126
_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)+(0.0461P)²+1.1647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.1018
_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:
 C00S(H00A,H00B), C00V(H00C,H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O), C00U(H00U), C010(H010),
 C011(H011), C014(H014), C017(H017), C019(H019), C01A(H01A), C01C(H01C),
 C01D(H01D), C01F(H01F)
2.c Idealised Me refined as rotating group:
 C01I(H01B,H01E,H01G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
S001 S 0.72244(5) 0.03748(2) 0.25297(3) 0.02572(13) Uani 1 1 d . . . . .
S004 S 0.68226(5) 0.30129(2) 0.26603(3) 0.02860(13) Uani 1 1 d . . . . .
O005 O 0.69711(17) 0.01408(8) 0.34227(8) 0.0381(3) Uani 1 1 d . . . . .
O007 O 0.87618(15) 0.01367(8) 0.21800(11) 0.0426(3) Uani 1 1 d . . . . .
N008 N 0.69231(16) 0.13878(8) 0.23395(8) 0.0224(3) Uani 1 1 d . . . . .
C00D C 0.72368(17) 0.19660(9) 0.29201(10) 0.0210(3) Uani 1 1 d . . . . .
C00E C 0.98492(18) 0.16831(9) 0.39031(9) 0.0207(3) Uani 1 1 d . . . . .
C00G C 0.55647(19) -0.00419(9) 0.18476(10) 0.0229(3) Uani 1 1 d . . . . .
C00J C 0.41766(19) 0.29425(10) 0.13750(10) 0.0243(3) Uani 1 1 d . . . . .
C00K C 1.0952(2) 0.21711(11) 0.34631(11) 0.0304(4) Uani 1 1 d . . . . .
H00K H 1.0545 0.2623 0.3100 0.037 Uiso 1 1 calc R . . . .
C00M C 0.3939(2) 0.00819(11) 0.20723(11) 0.0293(3) Uani 1 1 d . . . . .
H00M H 0.3726 0.0393 0.2584 0.035 Uiso 1 1 calc R . . . .
C00N C 0.3406(2) 0.21672(11) 0.12431(10) 0.0277(3) Uani 1 1 d . . . . .
H00N H 0.4061 0.1669 0.1247 0.033 Uiso 1 1 calc R . . . .
C00O C 0.5888(2) -0.05040(10) 0.11118(11) 0.0284(3) Uani 1 1 d . . . . .
H00O H 0.6999 -0.0588 0.0961 0.034 Uiso 1 1 calc R . . . .
C00S C 0.79990(18) 0.18855(10) 0.38568(10) 0.0242(3) Uani 1 1 d . . . . .
H00A H 0.7411 0.1435 0.4160 0.029 Uiso 1 1 calc R . . . .
H00B H 0.7832 0.2420 0.4173 0.029 Uiso 1 1 calc R . . . .
C00U C 1.0464(2) 0.10226(10) 0.44264(11) 0.0270(3) Uani 1 1 d . . . . .
H00U H 0.9715 0.0679 0.4722 0.032 Uiso 1 1 calc R . . . .
C00V C 0.60436(19) 0.30015(11) 0.15112(11) 0.0288(4) Uani 1 1 d . . . . .
H00C H 0.6415 0.3521 0.1225 0.035 Uiso 1 1 calc R . . . .
H00D H 0.6541 0.2517 0.1217 0.035 Uiso 1 1 calc R . . . .
C00Z C 0.2928(2) -0.07193(11) 0.08010(12) 0.0334(4) Uani 1 1 d . . . . .
C010 C 1.3252(2) 0.13481(13) 0.40866(11) 0.0336(4) Uani 1 1 d . . . . .
H010 H 1.4414 0.1238 0.4152 0.040 Uiso 1 1 calc R . . . .
C011 C 0.2632(2) -0.02541(11) 0.15407(12) 0.0327(4) Uani 1 1 d . . . . .
H011 H 0.1519 -0.0163 0.1687 0.039 Uiso 1 1 calc R . . . .
C014 C 0.3202(2) 0.36650(11) 0.13715(12) 0.0335(4) Uani 1 1 d . . . . .
H014 H 0.3713 0.4199 0.1472 0.040 Uiso 1 1 calc R . . . .
C017 C 1.2165(2) 0.08576(11) 0.45238(12) 0.0332(4) Uani 1 1 d . . . . .
H017 H 1.2575 0.0409 0.4890 0.040 Uiso 1 1 calc R . . . .
C019 C 1.2648(2) 0.20001(13) 0.35522(12) 0.0369(4) Uani 1 1 d . . . . .
H019 H 1.3397 0.2332 0.3245 0.044 Uiso 1 1 calc R . . . .
C01A C 0.1686(2) 0.21130(13) 0.11053(12) 0.0359(4) Uani 1 1 d . . . . .
H01A H 0.1166 0.1579 0.1025 0.043 Uiso 1 1 calc R . . . .
C01C C 0.4562(2) -0.08435(11) 0.05963(11) 0.0353(4) Uani 1 1 d . . . . .
H01C H 0.4777 -0.1167 0.0093 0.042 Uiso 1 1 calc R . . . .
C01D C 0.0731(2) 0.28354(14) 0.10854(12) 0.0388(4) Uani 1 1 d . . . . .
H01D H -0.0444 0.2800 0.0978 0.047 Uiso 1 1 calc R . . . .
C01F C 0.1482(2) 0.36091(13) 0.12220(12) 0.0392(4) Uani 1 1 d . . . . .
H01F H 0.0823 0.4105 0.1214 0.047 Uiso 1 1 calc R . . . .
C01I C 0.1499(3) -0.10757(15) 0.02190(15) 0.0523(6) Uani 1 1 d . . . . .
H01B H 0.0445 -0.0946 0.0473 0.078 Uiso 1 1 calc GR . . . .
H01E H 0.1625 -0.1688 0.0175 0.078 Uiso 1 1 calc GR . . . .
H01G H 0.1499 -0.0825 -0.0368 0.078 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
S001 O005 1.4405(13) . ?
S001 O007 1.4340(13) . ?
S001 N008 1.6496(13) . ?
S001 C00G 1.7615(15) . ?
S004 C00D 1.7358(15) . ?
S004 C00V 1.8178(17) . ?
N008 C00D 1.288(2) . ?
C00D C00S 1.518(2) . ?
C00E C00K 1.388(2) . ?
C00E C00S 1.521(2) . ?
C00E C00U 1.387(2) . ?
C00G C00M 1.391(2) . ?
C00G C00O 1.381(2) . ?
C00J C00N 1.387(2) . ?
C00J C00V 1.506(2) . ?
C00J C014 1.390(2) . ?
C00K H00K 0.9500 . ?
C00K C019 1.390(2) . ?
C00M H00M 0.9500 . ?
C00M C011 1.387(2) . ?
C00N H00N 0.9500 . ?
C00N C01A 1.389(2) . ?
C00O H00O 0.9500 . ?
C00O C01C 1.387(2) . ?
C00S H00A 0.9900 . ?
C00S H00B 0.9900 . ?
C00U H00U 0.9500 . ?
C00U C017 1.392(2) . ?
C00V H00C 0.9900 . ?
C00V H00D 0.9900 . ?
C00Z C011 1.383(3) . ?
C00Z C01C 1.389(3) . ?
C00Z C01I 1.511(2) . ?
C010 H010 0.9500 . ?
C010 C017 1.380(3) . ?
C010 C019 1.384(3) . ?
C011 H011 0.9500 . ?
C014 H014 0.9500 . ?
C014 C01F 1.390(3) . ?
C017 H017 0.9500 . ?
C019 H019 0.9500 . ?
C01A H01A 0.9500 . ?
C01A C01D 1.380(3) . ?
C01C H01C 0.9500 . ?
C01D H01D 0.9500 . ?
C01D C01F 1.379(3) . ?
C01F H01F 0.9500 . ?
C01I H01B 0.9800 . ?
C01I H01E 0.9800 . ?
C01I H01G 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
O005 S001 N008 112.87(7) . . ?
O005 S001 C00G 107.92(8) . . ?
O007 S001 O005 117.98(9) . . ?
O007 S001 N008 108.16(8) . . ?
O007 S001 C00G 108.65(8) . . ?
N008 S001 C00G 99.61(7) . . ?
C00D S004 C00V 104.92(8) . . ?
C00D N008 S001 123.75(11) . . ?
N008 C00D S004 120.07(12) . . ?
N008 C00D C00S 129.23(14) . . ?
C00S C00D S004 110.68(11) . . ?
C00K C00E C00S 121.24(14) . . ?
C00U C00E C00K 119.12(14) . . ?
C00U C00E C00S 119.57(13) . . ?
C00M C00G S001 119.24(12) . . ?
C00O C00G S001 119.97(12) . . ?
C00O C00G C00M 120.76(15) . . ?
C00N C00J C00V 120.45(14) . . ?
C00N C00J C014 119.08(15) . . ?
C014 C00J C00V 120.46(15) . . ?
C00E C00K H00K 119.9 . . ?
C00E C00K C019 120.17(16) . . ?
C019 C00K H00K 119.9 . . ?
C00G C00M H00M 120.4 . . ?
C011 C00M C00G 119.27(16) . . ?
C011 C00M H00M 120.4 . . ?
C00J C00N H00N 119.7 . . ?
C00J C00N C01A 120.51(16) . . ?
C01A C00N H00N 119.7 . . ?
C00G C00O H00O 120.5 . . ?
C00G C00O C01C 118.95(16) . . ?
C01C C00O H00O 120.5 . . ?
C00D C00S C00E 112.88(12) . . ?
C00D C00S H00A 109.0 . . ?
C00D C00S H00B 109.0 . . ?
C00E C00S H00A 109.0 . . ?
C00E C00S H00B 109.0 . . ?
H00A C00S H00B 107.8 . . ?
C00E C00U H00U 119.6 . . ?
C00E C00U C017 120.71(15) . . ?
C017 C00U H00U 119.6 . . ?
S004 C00V H00C 108.8 . . ?
S004 C00V H00D 108.8 . . ?
C00J C00V S004 113.85(12) . . ?
C00J C00V H00C 108.8 . . ?
C00J C00V H00D 108.8 . . ?
H00C C00V H00D 107.7 . . ?
C011 C00Z C01C 118.78(16) . . ?
C011 C00Z C01I 120.66(18) . . ?
C01C C00Z C01I 120.56(18) . . ?
C017 C010 H010 120.0 . . ?
C017 C010 C019 119.94(15) . . ?
C019 C010 H010 120.0 . . ?
C00M C011 H011 119.5 . . ?
C00Z C011 C00M 120.91(16) . . ?
C00Z C011 H011 119.5 . . ?
C00J C014 H014 119.9 . . ?
C01F C014 C00J 120.23(17) . . ?
C01F C014 H014 119.9 . . ?
C00U C017 H017 120.1 . . ?
C010 C017 C00U 119.77(16) . . ?
C010 C017 H017 120.1 . . ?
C00K C019 H019 119.9 . . ?
C010 C019 C00K 120.28(16) . . ?
C010 C019 H019 119.9 . . ?
C00N C01A H01A 120.0 . . ?
C01D C01A C00N 119.98(17) . . ?
C01D C01A H01A 120.0 . . ?
C00O C01C C00Z 121.32(16) . . ?
C00O C01C H01C 119.3 . . ?
C00Z C01C H01C 119.3 . . ?
C01A C01D H01D 120.0 . . ?
C01F C01D C01A 119.99(16) . . ?
C01F C01D H01D 120.0 . . ?
C014 C01F H01F 119.9 . . ?
C01D C01F C014 120.18(17) . . ?
C01D C01F H01F 119.9 . . ?
C00Z C01I H01B 109.5 . . ?
C00Z C01I H01E 109.5 . . ?
C00Z C01I H01G 109.5 . . ?
H01B C01I H01E 109.5 . . ?
H01B C01I H01G 109.5 . . ?
H01E C01I H01G 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
S001 N008 C00D S004 -178.30(8) . . . . ?
S001 N008 C00D C00S 3.3(2) . . . . ?
S001 C00G C00M C011 -179.29(13) . . . . ?
S001 C00G C00O C01C 178.42(13) . . . . ?
S004 C00D C00S C00E -106.65(13) . . . . ?
O005 S001 N008 C00D 32.26(15) . . . . ?
O005 S001 C00G C00M 48.74(15) . . . . ?
O005 S001 C00G C00O -129.59(13) . . . . ?
O007 S001 N008 C00D -100.15(14) . . . . ?
O007 S001 C00G C00M 177.76(13) . . . . ?
O007 S001 C00G C00O -0.57(16) . . . . ?
N008 S001 C00G C00M -69.24(14) . . . . ?
N008 S001 C00G C00O 112.43(13) . . . . ?
N008 C00D C00S C00E 71.8(2) . . . . ?
C00D S004 C00V C00J 92.66(13) . . . . ?
C00E C00K C019 C010 -0.6(3) . . . . ?
C00E C00U C017 C010 -0.9(3) . . . . ?
C00G S001 N008 C00D 146.47(13) . . . . ?
C00G C00M C011 C00Z 1.0(3) . . . . ?
C00G C00O C01C C00Z 0.7(3) . . . . ?
C00J C00N C01A C01D 1.0(3) . . . . ?
C00J C014 C01F C01D 0.7(3) . . . . ?
C00K C00E C00S C00D 52.9(2) . . . . ?
C00K C00E C00U C017 1.1(2) . . . . ?
C00M C00G C00O C01C 0.1(2) . . . . ?
C00N C00J C00V S004 -94.58(17) . . . . ?
C00N C00J C014 C01F -1.1(3) . . . . ?
C00N C01A C01D C01F -1.5(3) . . . . ?
C00O C00G C00M C011 -1.0(2) . . . . ?
C00S C00E C00K C019 176.65(15) . . . . ?
C00S C00E C00U C017 -175.94(15) . . . . ?
C00U C00E C00K C019 -0.4(2) . . . . ?
C00U C00E C00S C00D -130.06(15) . . . . ?
C00V S004 C00D N008 -1.97(14) . . . . ?
C00V S004 C00D C00S 176.68(10) . . . . ?
C00V C00J C00N C01A -179.11(15) . . . . ?
C00V C00J C014 C01F 178.26(16) . . . . ?
C011 C00Z C01C C00O -0.7(3) . . . . ?
C014 C00J C00N C01A 0.3(2) . . . . ?
C014 C00J C00V S004 86.03(17) . . . . ?
C017 C010 C019 C00K 0.9(3) . . . . ?
C019 C010 C017 C00U -0.2(3) . . . . ?
C01A C01D C01F C014 0.6(3) . . . . ?
C01C C00Z C011 C00M -0.2(3) . . . . ?
C01I C00Z C011 C00M -179.33(18) . . . . ?
C01I C00Z C01C C00O 178.46(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
