# Electronic Supplementary Material (ESI) for ChemComm.
# 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_BE27M
_database_code_depnum_ccdc_archive 'CCDC 2025452'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H26 N2 O4 S2'
_chemical_formula_sum            'C26 H26 N2 O4 S2'
_chemical_formula_weight         494.61

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                   16.1653(14)
_cell_length_b                   8.6116(7)
_cell_length_c                   18.7980(16)
_cell_angle_alpha                90
_cell_angle_beta                 111.5570(10)
_cell_angle_gamma                90
_cell_volume                     2433.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5938
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      22.35

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   0.906
_exptl_transmission_factor_max   0.934
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.254
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27135
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.086
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5569
_reflns_number_gt                3883
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+0.7376P] 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         5569
_refine_ls_number_parameters     340
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1296
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.008
_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 0.42677(19) 0.7855(2) 0.04683(15) 0.0492(5) Uani 0.752(14) 1 d . U P A 1
O1 O 0.4623(4) 0.7632(6) -0.0126(2) 0.0780(12) Uani 0.752(14) 1 d . U P A 1
O2 O 0.3715(2) 0.9191(3) 0.0404(3) 0.0716(14) Uani 0.752(14) 1 d . U P A 1
O2D O 0.3551(6) 0.9213(10) 0.0780(10) 0.069(3) Uani 0.248(14) 1 d . U P A 2
O1D O 0.4269(9) 0.8178(18) -0.0082(6) 0.067(4) Uani 0.248(14) 1 d . U P A 2
S1D S 0.4072(7) 0.8082(12) 0.0626(6) 0.0664(18) Uani 0.248(14) 1 d . U P A 2
N1 N 0.69847(11) 0.9719(2) 0.13608(10) 0.0524(4) Uani 1 1 d . . . . .
H1N H 0.6744(13) 1.000(2) 0.0889(12) 0.056(6) Uiso 1 1 d . . . . .
C1 C 0.78889(13) 0.9611(2) 0.17518(11) 0.0476(4) Uani 1 1 d . . . . .
S2 S 0.45907(4) 0.91921(8) 0.31412(4) 0.0736(2) Uani 1 1 d . . . . .
N2 N 0.54017(12) 0.9520(2) 0.28475(10) 0.0603(5) Uani 1 1 d . . . . .
C2 C 0.80224(12) 0.9299(2) 0.25205(11) 0.0460(4) Uani 1 1 d . . . . .
O3 O 0.38616(12) 0.8638(3) 0.24979(11) 0.0987(6) Uani 1 1 d . . . . .
C3 C 0.88916(13) 0.9139(2) 0.30479(12) 0.0530(5) Uani 1 1 d . . . . .
H3 H 0.900006 0.890509 0.355730 0.064 Uiso 1 1 calc R U . . .
O4 O 0.49345(14) 0.8276(2) 0.38230(11) 0.0921(6) Uani 1 1 d . . . . .
C4 C 0.95828(14) 0.9333(2) 0.27956(13) 0.0570(5) Uani 1 1 d . . . . .
H4 H 1.016491 0.924498 0.314203 0.068 Uiso 1 1 calc R U . . .
C5 C 0.94294(14) 0.9660(2) 0.20345(13) 0.0581(5) Uani 1 1 d . . . . .
H5 H 0.991465 0.979024 0.188689 0.070 Uiso 1 1 calc R U . . .
C6 C 0.85841(14) 0.9797(2) 0.14888(12) 0.0547(5) Uani 1 1 d . . . . .
C7 C 0.84276(16) 1.0158(3) 0.06697(13) 0.0756(7) Uani 1 1 d . . . . .
H7A H 0.798650 0.946263 0.034317 0.113 Uiso 1 1 calc R U . . .
H7B H 0.897276 1.003198 0.058242 0.113 Uiso 1 1 calc R U . . .
H7C H 0.822313 1.120874 0.055866 0.113 Uiso 1 1 calc R U . . .
C8 C 0.65533(12) 0.9523(2) 0.18677(11) 0.0475(4) Uani 1 1 d . . . . .
C9 C 0.71620(12) 0.9244(2) 0.25804(11) 0.0471(4) Uani 1 1 d . . . . .
C10 C 0.70060(14) 0.8906(3) 0.33028(12) 0.0601(5) Uani 1 1 d . . . . .
H10A H 0.755873 0.907274 0.373239 0.072 Uiso 1 1 calc R U . . .
H10B H 0.685356 0.781621 0.330268 0.072 Uiso 1 1 calc R U . . .
C11 C 0.62855(15) 0.9861(3) 0.34286(13) 0.0690(6) Uani 1 1 d . . . . .
H11A H 0.627984 0.964070 0.393289 0.083 Uiso 1 1 calc R U . . .
H11B H 0.641644 1.095555 0.340861 0.083 Uiso 1 1 calc R U . . .
C12 C 0.51823(14) 1.0351(2) 0.21165(13) 0.0601(5) Uani 1 1 d . . . . .
H12A H 0.541470 1.140028 0.221898 0.072 Uiso 1 1 calc R U . . .
H12B H 0.454066 1.042173 0.187012 0.072 Uiso 1 1 calc R U . . .
C13 C 0.55558(12) 0.9569(2) 0.15709(11) 0.0484(4) Uani 1 1 d . . . . .
H13 H 0.535962 1.018027 0.109799 0.058 Uiso 1 1 calc R U . . .
C14 C 0.51622(13) 0.7924(2) 0.13627(11) 0.0501(5) Uani 1 1 d . . . . .
H14A H 0.495607 0.756333 0.175776 0.060 Uiso 1 1 calc R U . A 1
H14B H 0.562678 0.722431 0.135049 0.060 Uiso 1 1 calc R U . A 1
C15 C 0.36494(13) 0.6180(3) 0.05353(11) 0.0548(5) Uani 1 1 d . . . . .
C16 C 0.38330(16) 0.4834(3) 0.02376(13) 0.0680(6) Uani 1 1 d . . . . .
H16 H 0.425050 0.482382 0.000452 0.082 Uiso 1 1 calc R U . . .
C17 C 0.3393(2) 0.3491(3) 0.02864(16) 0.0861(8) Uani 1 1 d . . . . .
H17 H 0.351556 0.256708 0.008827 0.103 Uiso 1 1 calc R U . . .
C18 C 0.2784(2) 0.3516(4) 0.06221(18) 0.0998(10) Uani 1 1 d . . . . .
H18 H 0.248635 0.260881 0.065080 0.120 Uiso 1 1 calc R U . . .
C19 C 0.2603(2) 0.4856(4) 0.0918(2) 0.1094(11) Uani 1 1 d . . . . .
H19 H 0.218154 0.486387 0.114742 0.131 Uiso 1 1 calc R U . . .
C20 C 0.30434(17) 0.6199(3) 0.08779(17) 0.0851(8) Uani 1 1 d . . . . .
H20 H 0.292626 0.711658 0.108466 0.102 Uiso 1 1 calc R U . . .
C21 C 0.42699(15) 1.1003(3) 0.34013(14) 0.0692(6) Uani 1 1 d . . . . .
C22 C 0.46867(17) 1.1543(3) 0.41404(15) 0.0779(7) Uani 1 1 d . . . . .
H22 H 0.513276 1.095979 0.449602 0.094 Uiso 1 1 calc R U . . .
C23 C 0.36182(17) 1.1868(4) 0.28718(17) 0.0892(9) Uani 1 1 d . . . . .
H23 H 0.334211 1.151550 0.237238 0.107 Uiso 1 1 calc R U . . .
C24 C 0.4437(2) 1.2952(4) 0.43467(19) 0.0977(10) Uani 1 1 d . . . . .
H24 H 0.471092 1.331700 0.484412 0.117 Uiso 1 1 calc R U . . .
C25 C 0.3793(3) 1.3805(5) 0.3825(2) 0.1117(11) Uani 1 1 d . . . . .
H25 H 0.363150 1.475947 0.396632 0.134 Uiso 1 1 calc R U . . .
C26 C 0.3380(2) 1.3279(5) 0.3097(2) 0.1106(12) Uani 1 1 d . . . . .
H26 H 0.293409 1.387228 0.274743 0.133 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
S1 O2 1.434(3) . ?
S1 O1 1.444(3) . ?
S1 C14 1.771(3) . ?
S1 C15 1.786(3) . ?
O2D S1D 1.386(12) . ?
O1D S1D 1.480(9) . ?
S1D C15 1.758(8) . ?
S1D C14 1.803(8) . ?
N1 C1 1.377(2) . ?
N1 C8 1.382(2) . ?
C1 C6 1.393(3) . ?
C1 C2 1.406(3) . ?
S2 O3 1.4255(19) . ?
S2 O4 1.4321(19) . ?
S2 N2 1.6233(18) . ?
S2 C21 1.768(3) . ?
N2 C12 1.473(3) . ?
N2 C11 1.474(3) . ?
C2 C3 1.397(3) . ?
C2 C9 1.437(3) . ?
C3 C4 1.375(3) . ?
C4 C5 1.388(3) . ?
C5 C6 1.380(3) . ?
C6 C7 1.498(3) . ?
C8 C9 1.361(3) . ?
C8 C13 1.501(3) . ?
C9 C10 1.498(3) . ?
C10 C11 1.514(3) . ?
C12 C13 1.525(3) . ?
C13 C14 1.543(3) . ?
C15 C20 1.356(3) . ?
C15 C16 1.367(3) . ?
C16 C17 1.378(3) . ?
C17 C18 1.350(4) . ?
C18 C19 1.359(4) . ?
C19 C20 1.375(4) . ?
C21 C23 1.373(4) . ?
C21 C22 1.383(3) . ?
C22 C24 1.379(4) . ?
C23 C26 1.387(5) . ?
C24 C25 1.354(5) . ?
C25 C26 1.361(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
O2 S1 O1 117.0(2) . . ?
O2 S1 C14 108.62(16) . . ?
O1 S1 C14 108.69(19) . . ?
O2 S1 C15 107.87(17) . . ?
O1 S1 C15 109.8(2) . . ?
C14 S1 C15 104.08(15) . . ?
O2D S1D O1D 119.8(7) . . ?
O2D S1D C15 115.6(6) . . ?
O1D S1D C15 99.7(6) . . ?
O2D S1D C14 112.9(6) . . ?
O1D S1D C14 102.8(6) . . ?
C15 S1D C14 103.9(5) . . ?
C1 N1 C8 109.23(16) . . ?
N1 C1 C6 129.74(18) . . ?
N1 C1 C2 107.06(17) . . ?
C6 C1 C2 123.18(18) . . ?
O3 S2 O4 120.18(13) . . ?
O3 S2 N2 106.81(10) . . ?
O4 S2 N2 107.69(11) . . ?
O3 S2 C21 107.14(13) . . ?
O4 S2 C21 107.17(12) . . ?
N2 S2 C21 107.24(10) . . ?
C12 N2 C11 115.48(18) . . ?
C12 N2 S2 117.01(15) . . ?
C11 N2 S2 117.80(15) . . ?
C3 C2 C1 118.85(18) . . ?
C3 C2 C9 133.72(18) . . ?
C1 C2 C9 107.42(16) . . ?
C4 C3 C2 118.42(19) . . ?
C3 C4 C5 121.33(19) . . ?
C6 C5 C4 122.5(2) . . ?
C5 C6 C1 115.72(19) . . ?
C5 C6 C7 121.94(19) . . ?
C1 C6 C7 122.33(19) . . ?
C9 C8 N1 109.55(17) . . ?
C9 C8 C13 131.31(17) . . ?
N1 C8 C13 119.07(17) . . ?
C8 C9 C2 106.71(16) . . ?
C8 C9 C10 128.69(18) . . ?
C2 C9 C10 124.59(17) . . ?
C9 C10 C11 115.55(18) . . ?
N2 C11 C10 111.57(18) . . ?
N2 C12 C13 113.18(17) . . ?
C8 C13 C12 113.49(17) . . ?
C8 C13 C14 110.90(15) . . ?
C12 C13 C14 110.34(16) . . ?
C13 C14 S1 112.86(14) . . ?
C13 C14 S1D 108.8(3) . . ?
C20 C15 C16 120.6(2) . . ?
C20 C15 S1D 105.4(6) . . ?
C16 C15 S1D 134.0(6) . . ?
C20 C15 S1 123.0(2) . . ?
C16 C15 S1 116.4(2) . . ?
C15 C16 C17 119.3(2) . . ?
C18 C17 C16 120.0(3) . . ?
C17 C18 C19 120.6(3) . . ?
C18 C19 C20 119.8(3) . . ?
C15 C20 C19 119.7(3) . . ?
C23 C21 C22 120.4(3) . . ?
C23 C21 S2 120.2(2) . . ?
C22 C21 S2 119.4(2) . . ?
C24 C22 C21 119.6(3) . . ?
C21 C23 C26 118.6(3) . . ?
C25 C24 C22 120.0(3) . . ?
C24 C25 C26 120.7(3) . . ?
C25 C26 C23 120.7(3) . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol and Dichloromethane'
####################################################################### 
# 
# 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_BE40M
_database_code_depnum_ccdc_archive 'CCDC 2025453'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H24 N2 O4 S2'
_chemical_formula_sum            'C21 H24 N2 O4 S2'
_chemical_formula_weight         432.54

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                   12.745(3)
_cell_length_b                   8.2887(17)
_cell_length_c                   20.697(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.665(3)
_cell_angle_gamma                90
_cell_volume                     2115.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9807
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.29

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.282
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.920
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23596
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.706
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4850
_reflns_number_gt                4496
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0618P)²+0.9197P] 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         4850
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_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 0.60928(4) 0.61997(6) 0.25769(2) 0.04044(15) Uani 1 1 d . . . . .
O1 O 0.72453(12) 0.5941(2) 0.27704(8) 0.0529(4) Uani 1 1 d . . . . .
N1 N 0.37604(13) 0.12755(19) 0.14743(9) 0.0378(4) Uani 1 1 d . . . . .
C1 C 0.34990(16) 0.0743(2) 0.08230(10) 0.0400(4) Uani 1 1 d . . . . .
H1N H 0.3488(18) 0.098(3) 0.1754(11) 0.040(6) Uiso 1 1 d . . . . .
S2 S 0.28880(4) 0.53883(6) 0.19743(3) 0.04295(15) Uani 1 1 d . . . . .
O2 O 0.55442(13) 0.6216(2) 0.30989(8) 0.0572(4) Uani 1 1 d . . . . .
N2 N 0.55020(12) 0.48859(19) 0.20021(7) 0.0346(3) Uani 1 1 d . . . . .
C2 C 0.28066(19) -0.0496(3) 0.05206(12) 0.0535(5) Uani 1 1 d . . . . .
H2 H 0.244315 -0.113360 0.076365 0.064 Uiso 1 1 calc R U . . .
O3 O 0.33745(14) 0.68092(19) 0.17811(10) 0.0647(5) Uani 1 1 d . . . . .
C3 C 0.2684(2) -0.0735(3) -0.01519(14) 0.0651(7) Uani 1 1 d . . . . .
H3 H 0.221329 -0.153530 -0.036938 0.078 Uiso 1 1 calc R U . . .
O4 O 0.21660(13) 0.5588(2) 0.24059(9) 0.0613(5) Uani 1 1 d . . . . .
C4 C 0.3244(2) 0.0186(3) -0.05147(12) 0.0664(7) Uani 1 1 d . . . . .
H4 H 0.314563 -0.001601 -0.096812 0.080 Uiso 1 1 calc R U . . .
C5 C 0.3939(2) 0.1389(3) -0.02165(11) 0.0567(6) Uani 1 1 d . . . . .
H5 H 0.431733 0.198952 -0.046294 0.068 Uiso 1 1 calc R U . . .
C6 C 0.40713(16) 0.1697(2) 0.04657(10) 0.0411(4) Uani 1 1 d . . . . .
C7 C 0.46824(15) 0.2840(2) 0.09297(9) 0.0368(4) Uani 1 1 d . . . . .
C8 C 0.44580(14) 0.2563(2) 0.15284(9) 0.0319(4) Uani 1 1 d . . . . .
C9 C 0.48628(14) 0.3495(2) 0.21705(9) 0.0312(4) Uani 1 1 d . . . . .
C10 C 0.55692(17) 0.2402(2) 0.27120(10) 0.0421(4) Uani 1 1 d . . . . .
H10A H 0.618032 0.201993 0.256398 0.063 Uiso 1 1 calc R U . . .
H10B H 0.514698 0.149916 0.279179 0.063 Uiso 1 1 calc R U . . .
H10C H 0.582024 0.300579 0.311762 0.063 Uiso 1 1 calc R U . . .
C11 C 0.61794(16) 0.4506(3) 0.15316(10) 0.0411(4) Uani 1 1 d . . . . .
H11A H 0.664434 0.359134 0.169774 0.049 Uiso 1 1 calc R U . . .
H11B H 0.663727 0.542230 0.150007 0.049 Uiso 1 1 calc R U . . .
C12 C 0.54585(18) 0.4117(3) 0.08479(10) 0.0459(5) Uani 1 1 d . . . . .
H12A H 0.506721 0.507467 0.065143 0.055 Uiso 1 1 calc R U . . .
H12B H 0.589365 0.374088 0.055562 0.055 Uiso 1 1 calc R U . . .
C13 C 0.5854(2) 0.8048(3) 0.21450(14) 0.0637(7) Uani 1 1 d . . . . .
H13A H 0.508762 0.823733 0.199902 0.096 Uiso 1 1 calc R U . . .
H13B H 0.615499 0.800776 0.176427 0.096 Uiso 1 1 calc R U . . .
H13C H 0.619062 0.890542 0.243619 0.096 Uiso 1 1 calc R U . . .
C14 C 0.38915(14) 0.4049(2) 0.24326(9) 0.0344(4) Uani 1 1 d . . . . .
H14A H 0.418929 0.454362 0.286489 0.041 Uiso 1 1 calc R U . . .
H14B H 0.351601 0.308061 0.251299 0.041 Uiso 1 1 calc R U . . .
C15 C 0.21302(16) 0.4421(2) 0.12505(10) 0.0421(4) Uani 1 1 d . . . . .
C16 C 0.13080(18) 0.3366(3) 0.12997(11) 0.0503(5) Uani 1 1 d . . . . .
H16 H 0.118918 0.312846 0.171466 0.060 Uiso 1 1 calc R U . . .
C17 C 0.0670(2) 0.2674(3) 0.07309(12) 0.0591(6) Uani 1 1 d . . . . .
H17 H 0.012209 0.196392 0.076524 0.071 Uiso 1 1 calc R U . . .
C18 C 0.0830(2) 0.3015(3) 0.01086(12) 0.0591(6) Uani 1 1 d . . . . .
C19 C 0.1654(2) 0.4064(4) 0.00711(12) 0.0644(7) Uani 1 1 d . . . . .
H19 H 0.177141 0.429779 -0.034443 0.077 Uiso 1 1 calc R U . . .
C20 C 0.23097(19) 0.4779(3) 0.06356(12) 0.0539(6) Uani 1 1 d . . . . .
H20 H 0.285980 0.548527 0.060114 0.065 Uiso 1 1 calc R U . . .
C21 C 0.0134(3) 0.2238(5) -0.05117(14) 0.0893(10) Uani 1 1 d . . . . .
H21A H -0.013261 0.305125 -0.084270 0.134 Uiso 1 1 calc R U . . .
H21B H -0.046654 0.169831 -0.040428 0.134 Uiso 1 1 calc R U . . .
H21C H 0.055839 0.146891 -0.068318 0.134 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
S1 O2 1.4278(16) . ?
S1 O1 1.4375(16) . ?
S1 N2 1.6476(16) . ?
S1 C13 1.761(2) . ?
N1 C8 1.375(2) . ?
N1 C1 1.377(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.406(3) . ?
S2 O3 1.4342(17) . ?
S2 O4 1.4451(16) . ?
S2 C15 1.757(2) . ?
S2 C14 1.7760(19) . ?
N2 C11 1.490(2) . ?
N2 C9 1.503(2) . ?
C2 C3 1.375(4) . ?
C3 C4 1.388(4) . ?
C4 C5 1.373(4) . ?
C5 C6 1.402(3) . ?
C6 C7 1.431(3) . ?
C7 C8 1.360(2) . ?
C7 C12 1.487(3) . ?
C8 C9 1.511(2) . ?
C9 C10 1.542(2) . ?
C9 C14 1.542(2) . ?
C11 C12 1.514(3) . ?
C15 C20 1.381(3) . ?
C15 C16 1.388(3) . ?
C16 C17 1.375(3) . ?
C17 C18 1.383(3) . ?
C18 C19 1.381(4) . ?
C18 C21 1.508(4) . ?
C19 C20 1.386(4) . ?

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 S1 O1 116.89(10) . . ?
O2 S1 N2 109.30(9) . . ?
O1 S1 N2 110.52(9) . . ?
O2 S1 C13 108.75(13) . . ?
O1 S1 C13 107.70(12) . . ?
N2 S1 C13 102.70(10) . . ?
C8 N1 C1 108.63(16) . . ?
N1 C1 C2 130.1(2) . . ?
N1 C1 C6 107.79(17) . . ?
C2 C1 C6 122.1(2) . . ?
O3 S2 O4 117.79(11) . . ?
O3 S2 C15 108.68(11) . . ?
O4 S2 C15 106.30(10) . . ?
O3 S2 C14 111.01(9) . . ?
O4 S2 C14 103.10(10) . . ?
C15 S2 C14 109.63(9) . . ?
C11 N2 C9 115.30(14) . . ?
C11 N2 S1 112.15(12) . . ?
C9 N2 S1 121.02(11) . . ?
C3 C2 C1 117.2(2) . . ?
C2 C3 C4 121.7(2) . . ?
C5 C4 C3 121.2(2) . . ?
C4 C5 C6 119.0(2) . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 134.6(2) . . ?
C1 C6 C7 106.62(17) . . ?
C8 C7 C6 107.17(17) . . ?
C8 C7 C12 121.56(17) . . ?
C6 C7 C12 131.25(17) . . ?
C7 C8 N1 109.75(16) . . ?
C7 C8 C9 127.69(16) . . ?
N1 C8 C9 122.55(15) . . ?
N2 C9 C8 105.83(13) . . ?
N2 C9 C10 111.62(15) . . ?
C8 C9 C10 110.23(15) . . ?
N2 C9 C14 112.56(14) . . ?
C8 C9 C14 109.63(15) . . ?
C10 C9 C14 107.00(14) . . ?
N2 C11 C12 109.93(16) . . ?
C7 C12 C11 107.98(16) . . ?
C9 C14 S2 122.14(12) . . ?
C20 C15 C16 120.5(2) . . ?
C20 C15 S2 120.25(18) . . ?
C16 C15 S2 119.15(16) . . ?
C17 C16 C15 119.6(2) . . ?
C16 C17 C18 121.2(2) . . ?
C19 C18 C17 118.3(2) . . ?
C19 C18 C21 120.9(3) . . ?
C17 C18 C21 120.8(3) . . ?
C18 C19 C20 121.8(2) . . ?
C15 C20 C19 118.7(2) . . ?

_refine_diff_density_max         0.353
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol and Dichloromethane'
