# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

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

data_MM1
_database_code_depnum_ccdc_archive 'CCDC 2246557'
loop_
_audit_author_name
_audit_author_address
'Susanta Dinda'
;Jadavpur University
India
;
_audit_update_record             
;
2023-03-06 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 N2 O S4'
_chemical_formula_weight         438.67

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   16.9533(15)
_cell_length_b                   7.7548(6)
_cell_length_c                   17.8906(15)
_cell_angle_alpha                90
_cell_angle_beta                 110.685(2)
_cell_angle_gamma                90
_cell_volume                     2200.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    250
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      27.8

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.445
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_absorpt_special_details   
;
?
;
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58496
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.057
_diffrn_reflns_theta_max         27.532
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4977
_reflns_number_gt                3887
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) 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     
'w=1/[σ²(Fo²)+12.3694P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4977
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1889
_refine_ls_R_factor_gt           0.1652
_refine_ls_wR_factor_ref         0.2800
_refine_ls_wR_factor_gt          0.2717
_refine_ls_goodness_of_fit_ref   1.562
_refine_ls_restrained_S_all      1.562
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50375(16) 0.0442(3) 0.26309(14) 0.0563(6) Uani 1 1 d . . . . .
S2 S 0.55427(14) 0.3184(3) 0.18037(16) 0.0615(7) Uani 1 1 d . . . . .
S3 S 0.43032(15) 0.6080(3) 0.14576(16) 0.0640(7) Uani 1 1 d . . . . .
S4 S 0.54156(17) 0.2980(3) 0.39955(15) 0.0639(7) Uani 1 1 d . . . . .
N1 N 0.5670(4) -0.0398(10) 0.4132(5) 0.060(2) Uani 1 1 d . . . . .
C2 C 0.3094(5) 0.2133(10) 0.1675(4) 0.0422(18) Uani 1 1 d . . . . .
N2 N 0.5674(5) 0.6023(10) 0.1064(5) 0.060(2) Uani 1 1 d . . . . .
O1 O 0.3855(4) 0.1738(11) 0.0816(4) 0.085(2) Uani 1 1 d . . . . .
C1 C 0.3873(5) 0.2128(12) 0.1465(5) 0.052(2) Uani 1 1 d . . . . .
C3 C 0.3072(5) 0.2635(12) 0.2406(5) 0.055(2) Uani 1 1 d . . . . .
H3 H 0.356396 0.300432 0.280326 0.066 Uiso 1 1 calc R U . . .
C7 C 0.2354(6) 0.1561(13) 0.1101(5) 0.060(2) Uani 1 1 d . . . . .
H7 H 0.235470 0.121862 0.060310 0.072 Uiso 1 1 calc R U . . .
C8 C 0.5410(5) 0.0972(11) 0.3671(5) 0.047(2) Uani 1 1 d . . . . .
C10 C 0.5184(5) 0.5255(11) 0.1403(5) 0.0454(19) Uani 1 1 d . . . . .
C4 C 0.2328(6) 0.2595(14) 0.2554(6) 0.064(3) Uani 1 1 d . . . . .
H4 H 0.231816 0.296050 0.304616 0.077 Uiso 1 1 calc R U . . .
C9 C 0.4711(5) 0.2495(10) 0.2140(5) 0.0452(19) Uani 1 1 d . . . . .
C6 C 0.1618(6) 0.1491(15) 0.1261(6) 0.074(3) Uani 1 1 d . . . . .
H6 H 0.112722 0.108283 0.087431 0.089 Uiso 1 1 calc R U . . .
C20 C 0.5714(6) -0.2166(12) 0.3846(7) 0.073(3) Uani 1 1 d . . . . .
H20A H 0.543765 -0.221309 0.327059 0.088 Uiso 1 1 calc R U . . .
H20B H 0.542593 -0.295459 0.408440 0.088 Uiso 1 1 calc R U . . .
C11 C 0.6470(6) 0.5322(13) 0.1050(7) 0.076(3) Uani 1 1 d . . . . .
H11A H 0.646063 0.529927 0.050455 0.092 Uiso 1 1 calc R U . . .
H11B H 0.654141 0.414919 0.125109 0.092 Uiso 1 1 calc R U . . .
C15 C 0.5526(7) 0.7776(14) 0.0750(6) 0.076(3) Uani 1 1 d . . . . .
H15A H 0.500145 0.820666 0.078048 0.091 Uiso 1 1 calc R U . . .
H15B H 0.547749 0.777480 0.019307 0.091 Uiso 1 1 calc R U . . .
C19 C 0.6626(7) -0.2692(14) 0.4072(9) 0.095(4) Uani 1 1 d . . . . .
H19A H 0.665473 -0.388731 0.392351 0.114 Uiso 1 1 calc R U . . .
H19B H 0.689130 -0.199230 0.377805 0.114 Uiso 1 1 calc R U . . .
C5 C 0.1607(6) 0.2020(15) 0.1983(6) 0.072(3) Uani 1 1 d . . . . .
H5 H 0.110670 0.198913 0.208623 0.086 Uiso 1 1 calc R U . . .
C16 C 0.6074(6) -0.0250(14) 0.5003(6) 0.071(3) Uani 1 1 d . . . . .
H16A H 0.580168 -0.102311 0.526340 0.085 Uiso 1 1 calc R U . . .
H16B H 0.601626 0.091889 0.516944 0.085 Uiso 1 1 calc R U . . .
C17 C 0.6997(6) -0.0709(15) 0.5241(7) 0.086(4) Uani 1 1 d . . . . .
H17A H 0.727581 0.012306 0.501379 0.103 Uiso 1 1 calc R U . . .
H17B H 0.726153 -0.066137 0.581809 0.103 Uiso 1 1 calc R U . . .
C13 C 0.7090(7) 0.8243(15) 0.1270(7) 0.082(3) Uani 1 1 d . . . . .
H13A H 0.714052 0.829759 0.074709 0.098 Uiso 1 1 calc R U . . .
H13B H 0.753264 0.895007 0.163298 0.098 Uiso 1 1 calc R U . . .
C12 C 0.7196(6) 0.6420(15) 0.1558(7) 0.079(3) Uani 1 1 d . . . . .
H12A H 0.722481 0.638471 0.210933 0.095 Uiso 1 1 calc R U . . .
H12B H 0.772076 0.596127 0.153818 0.095 Uiso 1 1 calc R U . . .
C14 C 0.6240(8) 0.8938(14) 0.1220(8) 0.091(4) Uani 1 1 d . . . . .
H14A H 0.623081 0.907357 0.175578 0.109 Uiso 1 1 calc R U . . .
H14B H 0.615803 1.006673 0.097072 0.109 Uiso 1 1 calc R U . . .
C18 C 0.7100(7) -0.2484(17) 0.4954(9) 0.110(5) Uani 1 1 d . . . . .
H18A H 0.689712 -0.332703 0.524361 0.132 Uiso 1 1 calc R U . . .
H18B H 0.769388 -0.270549 0.506624 0.132 Uiso 1 1 calc R U . . .
H9 H 0.468(4) 0.333(10) 0.249(4) 0.04(2) Uiso 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 C8 1.789(9) . ?
S1 C9 1.808(8) . ?
S2 C10 1.777(9) . ?
S2 C9 1.798(8) . ?
S3 C10 1.659(8) . ?
S4 C8 1.661(9) . ?
N1 C8 1.321(10) . ?
N1 C16 1.467(12) . ?
N1 C20 1.474(12) . ?
C2 C3 1.378(11) . ?
C2 C7 1.383(11) . ?
C2 C1 1.495(11) . ?
N2 C10 1.330(10) . ?
N2 C15 1.459(12) . ?
N2 C11 1.463(11) . ?
O1 C1 1.189(9) . ?
C1 C9 1.531(11) . ?
C3 C4 1.378(11) . ?
C7 C6 1.376(12) . ?
C4 C5 1.361(13) . ?
C6 C5 1.363(14) . ?
C20 C19 1.510(13) . ?
C11 C12 1.509(14) . ?
C15 C14 1.504(15) . ?
C19 C18 1.504(17) . ?
C16 C17 1.513(13) . ?
C17 C18 1.500(17) . ?
C13 C12 1.494(15) . ?
C13 C14 1.512(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C9 103.8(4) . . ?
C10 S2 C9 101.9(4) . . ?
C8 N1 C16 121.8(8) . . ?
C8 N1 C20 125.3(8) . . ?
C16 N1 C20 112.3(8) . . ?
C3 C2 C7 118.3(8) . . ?
C3 C2 C1 124.2(7) . . ?
C7 C2 C1 117.6(7) . . ?
C10 N2 C15 122.8(8) . . ?
C10 N2 C11 124.8(8) . . ?
C15 N2 C11 111.9(7) . . ?
O1 C1 C2 121.7(8) . . ?
O1 C1 C9 120.9(8) . . ?
C2 C1 C9 117.2(7) . . ?
C4 C3 C2 120.7(8) . . ?
C6 C7 C2 120.6(8) . . ?
N1 C8 S4 125.2(7) . . ?
N1 C8 S1 112.5(7) . . ?
S4 C8 S1 122.3(5) . . ?
N2 C10 S3 125.1(7) . . ?
N2 C10 S2 114.1(6) . . ?
S3 C10 S2 120.8(5) . . ?
C5 C4 C3 120.2(9) . . ?
C1 C9 S2 114.2(6) . . ?
C1 C9 S1 105.0(6) . . ?
S2 C9 S1 106.4(4) . . ?
C5 C6 C7 120.2(9) . . ?
N1 C20 C19 109.3(8) . . ?
N2 C11 C12 109.9(8) . . ?
N2 C15 C14 110.3(9) . . ?
C18 C19 C20 111.6(11) . . ?
C4 C5 C6 120.1(9) . . ?
N1 C16 C17 109.2(9) . . ?
C18 C17 C16 110.7(10) . . ?
C12 C13 C14 110.7(9) . . ?
C13 C12 C11 110.6(10) . . ?
C15 C14 C13 112.4(9) . . ?
C17 C18 C19 112.0(10) . . ?

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
C3 C2 C1 O1 -177.5(10) . . . . ?
C7 C2 C1 O1 4.0(14) . . . . ?
C3 C2 C1 C9 7.7(13) . . . . ?
C7 C2 C1 C9 -170.8(8) . . . . ?
C7 C2 C3 C4 -1.2(14) . . . . ?
C1 C2 C3 C4 -179.7(9) . . . . ?
C3 C2 C7 C6 -0.2(14) . . . . ?
C1 C2 C7 C6 178.4(9) . . . . ?
C16 N1 C8 S4 -5.9(12) . . . . ?
C20 N1 C8 S4 -176.1(7) . . . . ?
C16 N1 C8 S1 174.3(6) . . . . ?
C20 N1 C8 S1 4.1(11) . . . . ?
C9 S1 C8 N1 179.2(6) . . . . ?
C9 S1 C8 S4 -0.7(6) . . . . ?
C15 N2 C10 S3 5.0(13) . . . . ?
C11 N2 C10 S3 177.1(8) . . . . ?
C15 N2 C10 S2 -175.5(8) . . . . ?
C11 N2 C10 S2 -3.4(12) . . . . ?
C9 S2 C10 N2 -176.3(7) . . . . ?
C9 S2 C10 S3 3.2(6) . . . . ?
C2 C3 C4 C5 1.4(16) . . . . ?
O1 C1 C9 S2 25.2(12) . . . . ?
C2 C1 C9 S2 -160.0(6) . . . . ?
O1 C1 C9 S1 -91.0(10) . . . . ?
C2 C1 C9 S1 83.8(8) . . . . ?
C10 S2 C9 C1 68.6(7) . . . . ?
C10 S2 C9 S1 -176.0(4) . . . . ?
C8 S1 C9 C1 -137.3(5) . . . . ?
C8 S1 C9 S2 101.2(5) . . . . ?
C2 C7 C6 C5 1.3(17) . . . . ?
C8 N1 C20 C19 111.1(11) . . . . ?
C16 N1 C20 C19 -59.9(11) . . . . ?
C10 N2 C11 C12 -112.2(10) . . . . ?
C15 N2 C11 C12 60.6(12) . . . . ?
C10 N2 C15 C14 115.1(10) . . . . ?
C11 N2 C15 C14 -57.9(11) . . . . ?
N1 C20 C19 C18 54.3(12) . . . . ?
C3 C4 C5 C6 -0.3(17) . . . . ?
C7 C6 C5 C4 -1.0(18) . . . . ?
C8 N1 C16 C17 -110.1(10) . . . . ?
C20 N1 C16 C17 61.3(10) . . . . ?
N1 C16 C17 C18 -56.8(13) . . . . ?
C14 C13 C12 C11 53.8(13) . . . . ?
N2 C11 C12 C13 -58.1(12) . . . . ?
N2 C15 C14 C13 53.3(12) . . . . ?
C12 C13 C14 C15 -51.9(13) . . . . ?
C16 C17 C18 C19 53.3(14) . . . . ?
C20 C19 C18 C17 -52.4(14) . . . . ?

_refine_diff_density_max         0.607
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.069

