# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1822811'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H24 N2 O4 S2'
_chemical_formula_sum            'C23 H24 N2 O4 S2'
_chemical_formula_weight         456.56

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.143(3)
_cell_length_b                   10.204(2)
_cell_length_c                   18.499(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.972(12)
_cell_angle_gamma                90.00
_cell_volume                     2283.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6441
_cell_measurement_theta_min      1.68
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_T_max  0.943

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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_type  'Bruker APEX-II area-detector diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            75836
_diffrn_reflns_av_R_equivalents  0.0796
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         27.55
_reflns_number_total             5261
_reflns_number_gt                3670
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEXII (Bruker, 2006)'
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  SHELXTL

_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 > 2sigma(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     
'calc w=1/[σ²(Fo²)+(0.0551P)²+0.9143P] where P=(Fo²+2Fc²)/3'
_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_number_reflns         5261
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_ref          0.0878
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1209
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8209(4) -0.3798(4) 0.50987(18) 0.0959(12) Uani 1 1 d . . .
H1A H 0.8215 -0.4736 0.5013 0.115 Uiso 1 1 calc R . .
H1B H 0.7550 -0.3577 0.5334 0.115 Uiso 1 1 calc R . .
C2 C 0.7210(4) 0.7159(3) 0.2046(2) 0.1052(13) Uani 1 1 d . . .
H2A H 0.7309 0.7588 0.2509 0.158 Uiso 1 1 calc R . .
H2B H 0.6438 0.7142 0.1882 0.158 Uiso 1 1 calc R . .
H2C H 0.7608 0.7626 0.1701 0.158 Uiso 1 1 calc R . .
C3 C 0.4755(3) -0.0348(3) 0.15069(18) 0.0765(9) Uani 1 1 d . . .
H3A H 0.4088 -0.0633 0.1274 0.092 Uiso 1 1 calc R . .
C4 C 0.9207(3) -0.3397(3) 0.55520(18) 0.0872(10) Uani 1 1 d . . .
H4A H 0.9027 -0.3175 0.6038 0.105 Uiso 1 1 calc R . .
H4B H 0.9751 -0.4095 0.5584 0.105 Uiso 1 1 calc R . .
C5 C 0.5608(3) 0.0010(3) 0.10993(16) 0.0733(9) Uani 1 1 d . . .
H5A H 0.5497 -0.0037 0.0596 0.088 Uiso 1 1 calc R . .
C6 C 0.5314(3) -0.1665(3) 0.40620(19) 0.0885(11) Uani 1 1 d . . .
H6A H 0.4890 -0.1925 0.4453 0.133 Uiso 1 1 calc R . .
H6B H 0.6023 -0.2086 0.4115 0.133 Uiso 1 1 calc R . .
H6C H 0.4930 -0.1917 0.3608 0.133 Uiso 1 1 calc R . .
C7 C 0.7594(2) 0.4951(3) 0.15234(16) 0.0616(7) Uani 1 1 d . . .
H7A H 0.7317 0.5268 0.1072 0.074 Uiso 1 1 calc R . .
C8 C 0.7640(2) 0.5773(3) 0.21178(18) 0.0627(7) Uani 1 1 d . . .
C9 C 0.4880(2) -0.0288(3) 0.22479(16) 0.0663(8) Uani 1 1 d . . .
H9A H 0.4305 -0.0528 0.2522 0.080 Uiso 1 1 calc R . .
C10 C 0.6618(2) 0.0433(3) 0.14118(13) 0.0556(7) Uani 1 1 d . . .
H10A H 0.7186 0.0677 0.1133 0.067 Uiso 1 1 calc R . .
C11 C 0.8056(2) 0.5300(3) 0.27790(17) 0.0626(7) Uani 1 1 d . . .
H11A H 0.8090 0.5848 0.3182 0.075 Uiso 1 1 calc R . .
C12 C 0.9259(2) -0.2445(3) 0.44614(15) 0.0584(7) Uani 1 1 d . . .
H12A H 0.9796 -0.2973 0.4223 0.070 Uiso 1 1 calc R . .
C13 C 0.7951(2) 0.3662(3) 0.15851(13) 0.0514(6) Uani 1 1 d . . .
H13A H 0.7910 0.3114 0.1182 0.062 Uiso 1 1 calc R . .
C14 C 0.9109(2) -0.1134(3) 0.40911(13) 0.0532(6) Uani 1 1 d . . .
H14A H 0.8770 -0.1265 0.3602 0.064 Uiso 1 1 calc R . .
H14B H 0.9828 -0.0738 0.4055 0.064 Uiso 1 1 calc R . .
C15 C 0.5887(2) 0.0143(2) 0.25837(13) 0.0457(6) Uani 1 1 d . . .
C16 C 0.8424(2) 0.4032(3) 0.28566(14) 0.0552(6) Uani 1 1 d . . .
H16A H 0.8708 0.3725 0.3308 0.066 Uiso 1 1 calc R . .
C17 C 0.7598(2) 0.2038(2) 0.44825(13) 0.0513(6) Uani 1 1 d . . .
C18 C 0.62777(19) 0.0320(2) 0.33345(12) 0.0438(5) Uani 1 1 d . . .
C19 C 0.8095(2) 0.1035(2) 0.40389(11) 0.0435(5) Uani 1 1 d . . .
H19A H 0.8780 0.1401 0.3881 0.052 Uiso 1 1 calc R . .
C20 C 0.6745(2) 0.0478(2) 0.21670(12) 0.0415(5) Uani 1 1 d . . .
C21 C 0.8401(2) -0.0206(2) 0.44874(12) 0.0465(6) Uani 1 1 d . . .
H21A H 0.8797 0.0046 0.4944 0.056 Uiso 1 1 calc R . .
H21B H 0.7730 -0.0653 0.4595 0.056 Uiso 1 1 calc R . .
C22 C 0.73363(19) 0.0747(2) 0.33677(11) 0.0389(5) Uani 1 1 d . . .
C23 C 0.83687(19) 0.3211(2) 0.22575(12) 0.0417(5) Uani 1 1 d . . .
N1 N 0.76724(15) 0.08189(17) 0.26494(9) 0.0387(4) Uani 1 1 d . . .
N2 N 0.7247(2) 0.2830(2) 0.48274(13) 0.0753(7) Uani 1 1 d . . .
O1 O 0.82329(18) -0.3106(2) 0.44374(10) 0.0721(6) Uani 1 1 d . . .
O2 O 0.96081(16) -0.22965(19) 0.52043(10) 0.0660(5) Uani 1 1 d . . .
O3 O 0.89559(15) 0.10220(18) 0.16858(9) 0.0609(5) Uani 1 1 d . . .
O4 O 0.96323(13) 0.14989(19) 0.29507(10) 0.0594(5) Uani 1 1 d . . .
S1 S 0.87870(5) 0.15807(6) 0.23719(3) 0.04514(17) Uani 1 1 d . . .
S2 S 0.54984(6) 0.00858(8) 0.40811(4) 0.0630(2) 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
C1 O1 1.415(4) . ?
C1 C4 1.470(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C8 1.509(4) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 C9 1.367(4) . ?
C3 C5 1.382(5) . ?
C3 H3A 0.9300 . ?
C4 O2 1.402(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.379(4) . ?
C5 H5A 0.9300 . ?
C6 S2 1.800(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.380(4) . ?
C7 C13 1.386(4) . ?
C7 H7A 0.9300 . ?
C8 C11 1.370(4) . ?
C9 C15 1.395(3) . ?
C9 H9A 0.9300 . ?
C10 C20 1.393(3) . ?
C10 H10A 0.9300 . ?
C11 C16 1.372(4) . ?
C11 H11A 0.9300 . ?
C12 O2 1.411(3) . ?
C12 O1 1.414(3) . ?
C12 C14 1.507(4) . ?
C12 H12A 0.9800 . ?
C13 C23 1.381(3) . ?
C13 H13A 0.9300 . ?
C14 C21 1.510(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C20 1.391(3) . ?
C15 C18 1.440(3) . ?
C16 C23 1.386(3) . ?
C16 H16A 0.9300 . ?
C17 N2 1.136(3) . ?
C17 C19 1.473(3) . ?
C18 C22 1.354(3) . ?
C18 S2 1.757(2) . ?
C19 C22 1.509(3) . ?
C19 C21 1.542(3) . ?
C19 H19A 0.9800 . ?
C20 N1 1.418(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N1 1.425(3) . ?
C23 S1 1.747(2) . ?
N1 S1 1.6793(19) . ?
O3 S1 1.4224(18) . ?
O4 S1 1.4200(18) . ?

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
O1 C1 C4 106.1(3) . . ?
O1 C1 H1A 110.5 . . ?
C4 C1 H1A 110.5 . . ?
O1 C1 H1B 110.5 . . ?
C4 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
C8 C2 H2A 109.5 . . ?
C8 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C8 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C9 C3 C5 120.8(3) . . ?
C9 C3 H3A 119.6 . . ?
C5 C3 H3A 119.6 . . ?
O2 C4 C1 105.3(3) . . ?
O2 C4 H4A 110.7 . . ?
C1 C4 H4A 110.7 . . ?
O2 C4 H4B 110.7 . . ?
C1 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
C10 C5 C3 122.4(3) . . ?
C10 C5 H5A 118.8 . . ?
C3 C5 H5A 118.8 . . ?
S2 C6 H6A 109.5 . . ?
S2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
S2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C13 121.3(3) . . ?
C8 C7 H7A 119.3 . . ?
C13 C7 H7A 119.3 . . ?
C11 C8 C7 118.9(3) . . ?
C11 C8 C2 120.5(3) . . ?
C7 C8 C2 120.6(3) . . ?
C3 C9 C15 118.5(3) . . ?
C3 C9 H9A 120.7 . . ?
C15 C9 H9A 120.7 . . ?
C5 C10 C20 116.6(3) . . ?
C5 C10 H10A 121.7 . . ?
C20 C10 H10A 121.7 . . ?
C8 C11 C16 121.1(3) . . ?
C8 C11 H11A 119.4 . . ?
C16 C11 H11A 119.4 . . ?
O2 C12 O1 105.7(2) . . ?
O2 C12 C14 111.2(2) . . ?
O1 C12 C14 109.7(2) . . ?
O2 C12 H12A 110.0 . . ?
O1 C12 H12A 110.0 . . ?
C14 C12 H12A 110.0 . . ?
C23 C13 C7 118.6(2) . . ?
C23 C13 H13A 120.7 . . ?
C7 C13 H13A 120.7 . . ?
C12 C14 C21 112.8(2) . . ?
C12 C14 H14A 109.0 . . ?
C21 C14 H14A 109.0 . . ?
C12 C14 H14B 109.0 . . ?
C21 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C20 C15 C9 120.0(2) . . ?
C20 C15 C18 107.7(2) . . ?
C9 C15 C18 132.2(2) . . ?
C11 C16 C23 119.6(3) . . ?
C11 C16 H16A 120.2 . . ?
C23 C16 H16A 120.2 . . ?
N2 C17 C19 177.8(3) . . ?
C22 C18 C15 108.4(2) . . ?
C22 C18 S2 125.61(18) . . ?
C15 C18 S2 125.92(18) . . ?
C17 C19 C22 110.1(2) . . ?
C17 C19 C21 111.24(19) . . ?
C22 C19 C21 112.58(19) . . ?
C17 C19 H19A 107.6 . . ?
C22 C19 H19A 107.6 . . ?
C21 C19 H19A 107.6 . . ?
C15 C20 C10 121.7(2) . . ?
C15 C20 N1 107.66(19) . . ?
C10 C20 N1 130.7(2) . . ?
C14 C21 C19 112.00(19) . . ?
C14 C21 H21A 109.2 . . ?
C19 C21 H21A 109.2 . . ?
C14 C21 H21B 109.2 . . ?
C19 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C18 C22 N1 108.77(19) . . ?
C18 C22 C19 127.5(2) . . ?
N1 C22 C19 123.59(19) . . ?
C13 C23 C16 120.5(2) . . ?
C13 C23 S1 120.45(19) . . ?
C16 C23 S1 119.03(19) . . ?
C20 N1 C22 107.34(18) . . ?
C20 N1 S1 122.57(15) . . ?
C22 N1 S1 127.75(15) . . ?
C12 O1 C1 107.1(2) . . ?
C4 O2 C12 105.9(2) . . ?
O4 S1 O3 119.90(11) . . ?
O4 S1 N1 106.94(10) . . ?
O3 S1 N1 105.64(10) . . ?
O4 S1 C23 109.32(12) . . ?
O3 S1 C23 109.66(11) . . ?
N1 S1 C23 104.14(10) . . ?
C18 S2 C6 101.20(14) . . ?

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
O1 C1 C4 O2 13.1(4) . . . . ?
C9 C3 C5 C10 0.4(5) . . . . ?
C13 C7 C8 C11 0.4(4) . . . . ?
C13 C7 C8 C2 -177.8(3) . . . . ?
C5 C3 C9 C15 0.0(5) . . . . ?
C3 C5 C10 C20 0.4(4) . . . . ?
C7 C8 C11 C16 0.0(4) . . . . ?
C2 C8 C11 C16 178.3(3) . . . . ?
C8 C7 C13 C23 -0.6(4) . . . . ?
O2 C12 C14 C21 -50.7(3) . . . . ?
O1 C12 C14 C21 66.0(3) . . . . ?
C3 C9 C15 C20 -1.1(4) . . . . ?
C3 C9 C15 C18 179.8(3) . . . . ?
C8 C11 C16 C23 -0.4(4) . . . . ?
C20 C15 C18 C22 0.0(3) . . . . ?
C9 C15 C18 C22 179.2(3) . . . . ?
C20 C15 C18 S2 177.67(18) . . . . ?
C9 C15 C18 S2 -3.2(4) . . . . ?
N2 C17 C19 C22 -136(7) . . . . ?
N2 C17 C19 C21 99(7) . . . . ?
C9 C15 C20 C10 2.0(4) . . . . ?
C18 C15 C20 C10 -178.7(2) . . . . ?
C9 C15 C20 N1 -177.4(2) . . . . ?
C18 C15 C20 N1 1.8(3) . . . . ?
C5 C10 C20 C15 -1.6(4) . . . . ?
C5 C10 C20 N1 177.7(2) . . . . ?
C12 C14 C21 C19 -170.4(2) . . . . ?
C17 C19 C21 C14 -168.8(2) . . . . ?
C22 C19 C21 C14 67.1(3) . . . . ?
C15 C18 C22 N1 -1.8(3) . . . . ?
S2 C18 C22 N1 -179.52(17) . . . . ?
C15 C18 C22 C19 -178.4(2) . . . . ?
S2 C18 C22 C19 3.9(4) . . . . ?
C17 C19 C22 C18 -58.1(3) . . . . ?
C21 C19 C22 C18 66.6(3) . . . . ?
C17 C19 C22 N1 125.8(2) . . . . ?
C21 C19 C22 N1 -109.4(2) . . . . ?
C7 C13 C23 C16 0.3(4) . . . . ?
C7 C13 C23 S1 177.8(2) . . . . ?
C11 C16 C23 C13 0.2(4) . . . . ?
C11 C16 C23 S1 -177.4(2) . . . . ?
C15 C20 N1 C22 -2.9(2) . . . . ?
C10 C20 N1 C22 177.7(2) . . . . ?
C15 C20 N1 S1 -166.79(16) . . . . ?
C10 C20 N1 S1 13.9(3) . . . . ?
C18 C22 N1 C20 3.0(2) . . . . ?
C19 C22 N1 C20 179.68(19) . . . . ?
C18 C22 N1 S1 165.73(17) . . . . ?
C19 C22 N1 S1 -17.6(3) . . . . ?
O2 C12 O1 C1 -23.8(3) . . . . ?
C14 C12 O1 C1 -143.8(3) . . . . ?
C4 C1 O1 C12 6.5(4) . . . . ?
C1 C4 O2 C12 -27.8(4) . . . . ?
O1 C12 O2 C4 32.3(3) . . . . ?
C14 C12 O2 C4 151.4(3) . . . . ?
C20 N1 S1 O4 -167.07(17) . . . . ?
C22 N1 S1 O4 32.5(2) . . . . ?
C20 N1 S1 O3 -38.28(19) . . . . ?
C22 N1 S1 O3 161.33(18) . . . . ?
C20 N1 S1 C23 77.25(18) . . . . ?
C22 N1 S1 C23 -83.1(2) . . . . ?
C13 C23 S1 O4 151.68(19) . . . . ?
C16 C23 S1 O4 -30.7(2) . . . . ?
C13 C23 S1 O3 18.3(2) . . . . ?
C16 C23 S1 O3 -164.05(19) . . . . ?
C13 C23 S1 N1 -94.3(2) . . . . ?
C16 C23 S1 N1 83.3(2) . . . . ?
C22 C18 S2 C6 -113.9(2) . . . . ?
C15 C18 S2 C6 68.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1822813'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 N2 O2 S2'
_chemical_formula_sum            'C21 H22 N2 O2 S2'
_chemical_formula_weight         398.53

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.0286(6)
_cell_length_b                   24.0830(16)
_cell_length_c                   10.3285(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.965(3)
_cell_angle_gamma                90.00
_cell_volume                     2036.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      1.69
_cell_measurement_theta_max      27.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_T_max  0.956

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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_type  'Bruker APEX-II area-detector diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            67446
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         27.36
_reflns_number_total             4618
_reflns_number_gt                3954
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEXII (Bruker, 2006)'
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2002)'
_computing_publication_material  SHELXTL

_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 > 2sigma(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     
'calc w=1/[σ²(Fo²)+(0.0634P)²+0.9318P] where P=(Fo²+2Fc²)/3'
_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_number_reflns         4618
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_ref          0.0537
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0860(4) 0.03605(13) 0.1701(3) 0.0805(8) Uani 1 1 d . . .
H1A H 0.1487 0.0032 0.1754 0.121 Uiso 1 1 calc R . .
H1B H 0.1274 0.0664 0.1347 0.121 Uiso 1 1 calc R . .
H1C H -0.0264 0.0296 0.1067 0.121 Uiso 1 1 calc R . .
C2 C 0.5385(3) 0.11806(10) 0.5129(3) 0.0658(6) Uani 1 1 d . . .
H2A H 0.6124 0.0927 0.5836 0.079 Uiso 1 1 calc R . .
H2B H 0.4318 0.1142 0.5134 0.079 Uiso 1 1 calc R . .
C3 C 0.5262(4) 0.10197(12) 0.3679(3) 0.0715(7) Uani 1 1 d . . .
H3A H 0.4861 0.0646 0.3464 0.107 Uiso 1 1 calc R . .
H3B H 0.6323 0.1043 0.3676 0.107 Uiso 1 1 calc R . .
H3C H 0.4526 0.1267 0.2972 0.107 Uiso 1 1 calc R . .
C4 C 0.1668(3) 0.30007(9) 0.5845(2) 0.0553(5) Uani 1 1 d . . .
H4A H 0.1443 0.3332 0.5336 0.066 Uiso 1 1 calc R . .
C5 C 0.5846(3) 0.08164(11) 1.0537(2) 0.0684(7) Uani 1 1 d . . .
H5A H 0.6510 0.0506 1.1031 0.103 Uiso 1 1 calc R . .
H5B H 0.4791 0.0786 1.0547 0.103 Uiso 1 1 calc R . .
H5C H 0.6361 0.1155 1.1002 0.103 Uiso 1 1 calc R . .
C6 C 0.0193(3) 0.09610(9) 0.3378(2) 0.0570(5) Uani 1 1 d . . .
H6A H -0.0430 0.1182 0.2600 0.068 Uiso 1 1 calc R . .
C7 C 0.0553(3) 0.27905(9) 0.6322(2) 0.0556(5) Uani 1 1 d . . .
H7A H -0.0400 0.2989 0.6136 0.067 Uiso 1 1 calc R . .
C8 C 0.1896(3) 0.01745(9) 0.4340(2) 0.0578(5) Uani 1 1 d . . .
H8A H 0.2422 -0.0139 0.4214 0.069 Uiso 1 1 calc R . .
C9 C 0.2037(3) 0.03028(8) 0.5688(2) 0.0500(5) Uani 1 1 d . . .
H9A H 0.2658 0.0081 0.6466 0.060 Uiso 1 1 calc R . .
C10 C 0.6993(2) 0.24536(9) 0.7506(2) 0.0530(5) Uani 1 1 d . . .
C11 C 0.0992(3) 0.05015(9) 0.3169(2) 0.0542(5) Uani 1 1 d . . .
C12 C 0.0813(2) 0.22986(8) 0.7060(2) 0.0483(4) Uani 1 1 d . . .
H12A H 0.0070 0.2165 0.7392 0.058 Uiso 1 1 calc R . .
C13 C 0.5982(3) 0.17670(9) 0.5550(2) 0.0519(5) Uani 1 1 d . . .
H13A H 0.5179 0.2025 0.4913 0.062 Uiso 1 1 calc R . .
H13B H 0.6990 0.1820 0.5445 0.062 Uiso 1 1 calc R . .
C14 C 0.0303(2) 0.10969(8) 0.4708(2) 0.0488(4) Uani 1 1 d . . .
H14A H -0.0242 0.1406 0.4831 0.059 Uiso 1 1 calc R . .
C15 C 0.3104(3) 0.27228(8) 0.6120(2) 0.0481(4) Uani 1 1 d . . .
H15A H 0.3864 0.2868 0.5823 0.058 Uiso 1 1 calc R . .
C16 C 0.6281(2) 0.18953(8) 0.7107(2) 0.0437(4) Uani 1 1 d . . .
H16A H 0.7080 0.1626 0.7727 0.052 Uiso 1 1 calc R . .
C17 C 0.4750(2) 0.18374(7) 0.73411(18) 0.0362(4) Uani 1 1 d . . .
C18 C 0.2234(2) 0.20098(7) 0.72887(18) 0.0361(4) Uani 1 1 d . . .
C19 C 0.4395(2) 0.14053(7) 0.80066(18) 0.0365(4) Uani 1 1 d . . .
C20 C 0.1240(2) 0.07660(7) 0.58641(19) 0.0393(4) Uani 1 1 d . . .
C21 C 0.3395(2) 0.22190(7) 0.68541(18) 0.0363(4) Uani 1 1 d . . .
N1 N 0.7548(3) 0.28855(9) 0.7776(3) 0.0767(7) Uani 1 1 d . . .
N2 N 0.28172(17) 0.14933(6) 0.80082(15) 0.0367(3) Uani 1 1 d . . .
O1 O -0.00089(18) 0.11847(7) 0.75117(18) 0.0574(4) Uani 1 1 d . . .
O2 O 0.2244(2) 0.05196(6) 0.85649(16) 0.0565(4) Uani 1 1 d . . .
S1 S 0.14721(6) 0.095622(19) 0.75790(5) 0.04190(14) Uani 1 1 d . . .
S2 S 0.56132(7) 0.08230(2) 0.87123(6) 0.05127(16) 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
C1 C11 1.509(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.506(3) . ?
C2 C13 1.509(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C15 1.378(3) . ?
C4 C7 1.389(3) . ?
C4 H4A 0.9300 . ?
C5 S2 1.806(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C14 1.375(3) . ?
C6 C11 1.386(3) . ?
C6 H6A 0.9300 . ?
C7 C12 1.374(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.379(3) . ?
C8 C11 1.384(3) . ?
C8 H8A 0.9300 . ?
C9 C20 1.380(3) . ?
C9 H9A 0.9300 . ?
C10 N1 1.137(3) . ?
C10 C16 1.472(3) . ?
C12 C18 1.390(2) . ?
C12 H12A 0.9300 . ?
C13 C16 1.545(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C20 1.387(3) . ?
C14 H14A 0.9300 . ?
C15 C21 1.395(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.507(2) . ?
C16 H16A 0.9800 . ?
C17 C19 1.358(2) . ?
C17 C21 1.441(2) . ?
C18 C21 1.396(2) . ?
C18 N2 1.430(2) . ?
C19 N2 1.441(2) . ?
C19 S2 1.7411(18) . ?
C20 S1 1.7543(19) . ?
N2 S1 1.7000(15) . ?
O1 S1 1.4203(15) . ?
O2 S1 1.4245(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
C11 C1 H1A 109.5 . . ?
C11 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C11 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C13 113.3(2) . . ?
C3 C2 H2A 108.9 . . ?
C13 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C13 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C15 C4 C7 120.64(19) . . ?
C15 C4 H4A 119.7 . . ?
C7 C4 H4A 119.7 . . ?
S2 C5 H5A 109.5 . . ?
S2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
S2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C14 C6 C11 121.5(2) . . ?
C14 C6 H6A 119.3 . . ?
C11 C6 H6A 119.3 . . ?
C12 C7 C4 122.06(19) . . ?
C12 C7 H7A 119.0 . . ?
C4 C7 H7A 119.0 . . ?
C9 C8 C11 121.6(2) . . ?
C9 C8 H8A 119.2 . . ?
C11 C8 H8A 119.2 . . ?
C8 C9 C20 118.87(19) . . ?
C8 C9 H9A 120.6 . . ?
C20 C9 H9A 120.6 . . ?
N1 C10 C16 177.9(3) . . ?
C8 C11 C6 118.2(2) . . ?
C8 C11 C1 121.1(2) . . ?
C6 C11 C1 120.7(2) . . ?
C7 C12 C18 117.05(18) . . ?
C7 C12 H12A 121.5 . . ?
C18 C12 H12A 121.5 . . ?
C2 C13 C16 111.78(18) . . ?
C2 C13 H13A 109.3 . . ?
C16 C13 H13A 109.3 . . ?
C2 C13 H13B 109.3 . . ?
C16 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C6 C14 C20 118.96(19) . . ?
C6 C14 H14A 120.5 . . ?
C20 C14 H14A 120.5 . . ?
C4 C15 C21 118.62(19) . . ?
C4 C15 H15A 120.7 . . ?
C21 C15 H15A 120.7 . . ?
C10 C16 C17 111.18(16) . . ?
C10 C16 C13 109.75(17) . . ?
C17 C16 C13 112.30(15) . . ?
C10 C16 H16A 107.8 . . ?
C17 C16 H16A 107.8 . . ?
C13 C16 H16A 107.8 . . ?
C19 C17 C21 108.55(15) . . ?
C19 C17 C16 125.51(16) . . ?
C21 C17 C16 125.91(16) . . ?
C12 C18 C21 121.97(17) . . ?
C12 C18 N2 129.36(16) . . ?
C21 C18 N2 108.63(14) . . ?
C17 C19 N2 109.44(15) . . ?
C17 C19 S2 125.92(13) . . ?
N2 C19 S2 124.62(13) . . ?
C9 C20 C14 120.91(18) . . ?
C9 C20 S1 119.80(15) . . ?
C14 C20 S1 119.25(15) . . ?
C15 C21 C18 119.59(16) . . ?
C15 C21 C17 132.95(17) . . ?
C18 C21 C17 107.44(15) . . ?
C18 N2 C19 105.92(13) . . ?
C18 N2 S1 117.42(11) . . ?
C19 N2 S1 119.05(11) . . ?
O1 S1 O2 119.16(10) . . ?
O1 S1 N2 105.79(8) . . ?
O2 S1 N2 107.18(8) . . ?
O1 S1 C20 110.05(9) . . ?
O2 S1 C20 110.06(9) . . ?
N2 S1 C20 103.28(8) . . ?
C19 S2 C5 102.63(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
C15 C4 C7 C12 -1.0(3) . . . . ?
C11 C8 C9 C20 0.6(3) . . . . ?
C9 C8 C11 C6 -1.2(3) . . . . ?
C9 C8 C11 C1 179.4(2) . . . . ?
C14 C6 C11 C8 0.8(3) . . . . ?
C14 C6 C11 C1 -179.8(2) . . . . ?
C4 C7 C12 C18 -1.3(3) . . . . ?
C3 C2 C13 C16 -173.5(2) . . . . ?
C11 C6 C14 C20 0.2(3) . . . . ?
C7 C4 C15 C21 1.7(3) . . . . ?
N1 C10 C16 C17 -132(7) . . . . ?
N1 C10 C16 C13 -7(7) . . . . ?
C2 C13 C16 C10 175.18(19) . . . . ?
C2 C13 C16 C17 -60.6(2) . . . . ?
C10 C16 C17 C19 -132.9(2) . . . . ?
C13 C16 C17 C19 103.7(2) . . . . ?
C10 C16 C17 C21 49.5(2) . . . . ?
C13 C16 C17 C21 -73.9(2) . . . . ?
C7 C12 C18 C21 3.0(3) . . . . ?
C7 C12 C18 N2 -179.79(18) . . . . ?
C21 C17 C19 N2 -1.25(19) . . . . ?
C16 C17 C19 N2 -179.19(16) . . . . ?
C21 C17 C19 S2 177.14(13) . . . . ?
C16 C17 C19 S2 -0.8(3) . . . . ?
C8 C9 C20 C14 0.4(3) . . . . ?
C8 C9 C20 S1 -177.15(16) . . . . ?
C6 C14 C20 C9 -0.8(3) . . . . ?
C6 C14 C20 S1 176.75(16) . . . . ?
C4 C15 C21 C18 0.0(3) . . . . ?
C4 C15 C21 C17 -178.03(19) . . . . ?
C12 C18 C21 C15 -2.4(3) . . . . ?
N2 C18 C21 C15 179.87(16) . . . . ?
C12 C18 C21 C17 176.06(16) . . . . ?
N2 C18 C21 C17 -1.63(18) . . . . ?
C19 C17 C21 C15 -179.98(19) . . . . ?
C16 C17 C21 C15 -2.1(3) . . . . ?
C19 C17 C21 C18 1.79(19) . . . . ?
C16 C17 C21 C18 179.72(16) . . . . ?
C12 C18 N2 C19 -176.58(18) . . . . ?
C21 C18 N2 C19 0.88(17) . . . . ?
C12 C18 N2 S1 47.6(2) . . . . ?
C21 C18 N2 S1 -134.92(13) . . . . ?
C17 C19 N2 C18 0.25(18) . . . . ?
S2 C19 N2 C18 -178.17(12) . . . . ?
C17 C19 N2 S1 135.19(13) . . . . ?
S2 C19 N2 S1 -43.23(19) . . . . ?
C18 N2 S1 O1 -43.46(14) . . . . ?
C19 N2 S1 O1 -173.39(13) . . . . ?
C18 N2 S1 O2 -171.59(12) . . . . ?
C19 N2 S1 O2 58.48(15) . . . . ?
C18 N2 S1 C20 72.19(13) . . . . ?
C19 N2 S1 C20 -57.73(14) . . . . ?
C9 C20 S1 O1 -145.09(16) . . . . ?
C14 C20 S1 O1 37.31(18) . . . . ?
C9 C20 S1 O2 -11.82(19) . . . . ?
C14 C20 S1 O2 170.58(15) . . . . ?
C9 C20 S1 N2 102.34(16) . . . . ?
C14 C20 S1 N2 -75.26(16) . . . . ?
C17 C19 S2 C5 125.44(18) . . . . ?
N2 C19 S2 C5 -56.40(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.36
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.054


