# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1482137'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2016-07-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H17 N O4 S2'
_chemical_formula_sum            'C20 H17 N O4 S2'
_chemical_formula_weight         399.47

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   P21/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                   14.0128(17)
_cell_length_b                   8.8244(11)
_cell_length_c                   16.431(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.361(2)
_cell_angle_gamma                90.00
_cell_volume                     1879.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2134
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      28.32

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8914
_exptl_absorpt_correction_T_max  0.9407
_exptl_absorpt_process_details   'SADABS (Bruker 2002)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(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 Smart Apex CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11525
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3687
_reflns_number_gt                2422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0696P)²+1.1866P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3687
_refine_ls_number_parameters     244
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1690
_refine_ls_wR_factor_gt          0.1508
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.058
_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 0.0937(3) 0.1233(5) 0.2303(3) 0.0827(13) Uani 1 1 d D . .
H1 H 0.1541 0.1500 0.2769 0.099 Uiso 1 1 calc R . .
C2 C 0.0167(4) 0.0413(6) 0.2464(3) 0.1006(17) Uani 1 1 d D . .
H2 H 0.0255 0.0110 0.3030 0.121 Uiso 1 1 calc R . .
C3 C -0.0713(4) 0.0076(5) 0.1762(4) 0.1006(18) Uani 1 1 d D . .
H3 H -0.1229 -0.0480 0.1851 0.121 Uiso 1 1 calc R . .
C4 C -0.0850(4) 0.0528(6) 0.0948(4) 0.1050(17) Uani 1 1 d D . .
H4 H -0.1466 0.0317 0.0481 0.126 Uiso 1 1 calc R . .
C5 C -0.0102(4) 0.1281(6) 0.0809(3) 0.0878(14) Uani 1 1 d D . .
H5 H -0.0207 0.1569 0.0237 0.105 Uiso 1 1 calc R . .
C6 C 0.0800(3) 0.1642(4) 0.1461(3) 0.0636(10) Uani 1 1 d DU . .
C7 C 0.1654(4) 0.2501(5) 0.1352(4) 0.0973(16) Uani 1 1 d U . .
H7 H 0.2122 0.2903 0.1875 0.117 Uiso 1 1 calc R . .
C8 C 0.1851(4) 0.2765(5) 0.0750(4) 0.1000(17) Uani 1 1 d . . .
H8 H 0.1409 0.2272 0.0247 0.120 Uiso 1 1 calc R . .
C9 C 0.2399(3) 0.6575(4) 0.0978(2) 0.0540(9) Uani 1 1 d . . .
C10 C 0.1666(3) 0.6679(4) 0.1356(3) 0.0699(11) Uani 1 1 d . . .
H10 H 0.1056 0.6127 0.1133 0.084 Uiso 1 1 calc R . .
C11 C 0.1872(4) 0.7626(5) 0.2072(3) 0.0884(14) Uani 1 1 d . . .
H11 H 0.1396 0.7713 0.2339 0.106 Uiso 1 1 calc R . .
C12 C 0.2776(4) 0.8439(5) 0.2391(3) 0.0846(13) Uani 1 1 d . . .
H12 H 0.2909 0.9071 0.2875 0.102 Uiso 1 1 calc R . .
C13 C 0.3482(4) 0.8331(5) 0.2006(3) 0.0785(12) Uani 1 1 d . . .
H13 H 0.4088 0.8894 0.2226 0.094 Uiso 1 1 calc R . .
C14 C 0.3303(3) 0.7393(4) 0.1292(3) 0.0640(10) Uani 1 1 d . . .
H14 H 0.3782 0.7315 0.1029 0.077 Uiso 1 1 calc R . .
C15 C 0.3823(2) 0.2093(4) -0.0083(2) 0.0486(8) Uani 1 1 d . . .
C16 C 0.3612(3) 0.0562(4) -0.0164(2) 0.0573(9) Uani 1 1 d . . .
H16 H 0.3463 0.0046 0.0267 0.069 Uiso 1 1 calc R . .
C17 C 0.3627(3) -0.0188(5) -0.0890(3) 0.0698(11) Uani 1 1 d . . .
H17 H 0.3486 -0.1221 -0.0954 0.084 Uiso 1 1 calc R . .
C18 C 0.3847(3) 0.0575(6) -0.1520(3) 0.0740(12) Uani 1 1 d . . .
H18 H 0.3849 0.0057 -0.2012 0.089 Uiso 1 1 calc R . .
C19 C 0.4065(3) 0.2097(6) -0.1437(2) 0.0712(12) Uani 1 1 d . . .
H19 H 0.4216 0.2603 -0.1870 0.085 Uiso 1 1 calc R . .
C20 C 0.4060(3) 0.2878(4) -0.0706(2) 0.0593(9) Uani 1 1 d . . .
H20 H 0.4213 0.3907 -0.0638 0.071 Uiso 1 1 calc R . .
N1 N 0.2594(2) 0.3650(3) 0.05795(19) 0.0583(8) Uani 1 1 d . . .
O1 O 0.44536(19) 0.4341(3) 0.10197(16) 0.0677(7) Uani 1 1 d . . .
O2 O 0.3972(2) 0.1947(3) 0.15275(15) 0.0687(7) Uani 1 1 d . . .
O3 O 0.1083(2) 0.5152(4) -0.03512(18) 0.0889(9) Uani 1 1 d . . .
O4 O 0.2791(2) 0.5734(3) -0.03766(18) 0.0824(9) Uani 1 1 d . . .
S1 S 0.38165(7) 0.30416(10) 0.08554(5) 0.0530(3) Uani 1 1 d . . .
S2 S 0.21709(8) 0.53338(12) 0.00950(6) 0.0636(3) 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 C6 1.370(5) . ?
C1 C2 1.405(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.338(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.332(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.348(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.484(6) . ?
C7 C8 1.147(6) . ?
C7 H7 0.9300 . ?
C8 N1 1.412(5) . ?
C8 H8 0.9300 . ?
C9 C14 1.377(5) . ?
C9 C10 1.390(5) . ?
C9 S2 1.747(4) . ?
C10 C11 1.381(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.377(5) . ?
C15 C16 1.379(5) . ?
C15 S1 1.758(3) . ?
C16 C17 1.371(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.388(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N1 S2 1.683(3) . ?
N1 S1 1.685(3) . ?
O1 S1 1.414(3) . ?
O2 S1 1.420(2) . ?
O3 S2 1.427(3) . ?
O4 S2 1.412(3) . ?

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
C6 C1 C2 120.2(4) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 117.7(4) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C4 C3 C2 121.4(5) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 122.8(5) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C5 C6 C1 118.0(4) . . ?
C5 C6 C7 125.5(5) . . ?
C1 C6 C7 116.5(4) . . ?
C8 C7 C6 132.6(6) . . ?
C8 C7 H7 113.7 . . ?
C6 C7 H7 113.7 . . ?
C7 C8 N1 136.1(6) . . ?
C7 C8 H8 112.0 . . ?
N1 C8 H8 112.0 . . ?
C14 C9 C10 121.8(4) . . ?
C14 C9 S2 119.5(3) . . ?
C10 C9 S2 118.6(3) . . ?
C11 C10 C9 118.1(4) . . ?
C11 C10 H10 121.0 . . ?
C9 C10 H10 121.0 . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.5(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 118.6(4) . . ?
C9 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C20 C15 C16 121.7(3) . . ?
C20 C15 S1 119.7(3) . . ?
C16 C15 S1 118.6(3) . . ?
C17 C16 C15 118.9(4) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 121.0(4) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C20 119.8(4) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 118.4(4) . . ?
C15 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C8 N1 S2 115.4(3) . . ?
C8 N1 S1 121.4(3) . . ?
S2 N1 S1 123.19(17) . . ?
O1 S1 O2 120.24(16) . . ?
O1 S1 N1 107.25(15) . . ?
O2 S1 N1 105.40(15) . . ?
O1 S1 C15 109.87(16) . . ?
O2 S1 C15 107.93(16) . . ?
N1 S1 C15 105.07(15) . . ?
O4 S2 O3 120.43(18) . . ?
O4 S2 N1 107.52(16) . . ?
O3 S2 N1 104.98(17) . . ?
O4 S2 C9 110.02(18) . . ?
O3 S2 C9 108.62(18) . . ?
N1 S2 C9 103.91(15) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.001
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.055
