# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_cu_0901nfyk_0m
_database_code_depnum_ccdc_archive 'CCDC 1502249'
_audit_update_record             
;
2016-09-02 deposited with the CCDC.
2017-07-13 downloaded from the CCDC.
;
_audit_creation_date             2016-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H20 O4 S2'
_chemical_formula_sum            'C22 H20 O4 S2'
_chemical_formula_weight         412.50
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   6.8674(3)
_cell_length_b                   13.0958(6)
_cell_length_c                   22.6828(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2039.96(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9720
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.242
_cell_measurement_theta_min      3.375
_exptl_absorpt_coefficient_mu    2.578
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.2959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1425 before and 0.0735 after correction.
The Ratio of minimum to maximum transmission is 0.3929.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20278
_diffrn_reflns_theta_full        68.30
_diffrn_reflns_theta_max         68.30
_diffrn_reflns_theta_min         5.16
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3642
_reflns_number_total             3677
_reflns_threshold_expression     >2sigma(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.069(14)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3677
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0569P)²+0.1956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0880
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S -0.99560(7) -0.61306(3) -0.144888(18) 0.04170(13) Uani 1 d . . .
S2 S -0.90164(8) -0.63691(3) 0.045298(18) 0.04368(13) Uani 1 d . . .
O1 O -0.9095(3) -0.51555(10) -0.15648(6) 0.0565(4) Uani 1 d . . .
C2 C -0.6357(4) -0.85333(17) -0.23757(9) 0.0544(5) Uani 1 d . . .
O3 O -0.7109(2) -0.63429(12) 0.07097(7) 0.0586(4) Uani 1 d . . .
O4 O -1.0058(3) -0.73155(10) 0.04322(7) 0.0629(4) Uani 1 d . . .
C5 C -0.8800(3) -0.58983(11) -0.02917(7) 0.0375(3) Uani 1 d . . .
C6 C -1.0470(3) -0.54424(14) 0.08008(7) 0.0433(4) Uani 1 d . . .
O7 O -1.1964(2) -0.62969(13) -0.15981(7) 0.0621(4) Uani 1 d . . .
C8 C -0.7485(3) -0.50084(12) -0.03807(7) 0.0393(4) Uani 1 d . . .
C9 C -0.9786(3) -0.64244(13) -0.06906(7) 0.0401(3) Uani 1 d . . .
H9 H -1.0450 -0.7001 -0.0560 0.048 Uiso 1 calc . . R
C10 C -0.8126(4) -0.40196(14) -0.02798(10) 0.0564(5) Uani 1 d . . .
H10 H -0.9383 -0.3902 -0.0144 0.068 Uiso 1 calc . . R
C11 C -0.8555(3) -0.70811(13) -0.17876(7) 0.0390(4) Uani 1 d . . .
C12 C -0.9432(3) -0.79725(15) -0.19841(9) 0.0512(5) Uani 1 d . . .
H12 H -1.0749 -0.8090 -0.1916 0.061 Uiso 1 calc . . R
C13 C -0.5595(3) -0.51750(14) -0.05666(8) 0.0460(4) Uani 1 d . . .
H13 H -0.5153 -0.5839 -0.0625 0.055 Uiso 1 calc . . R
C14 C -0.6582(3) -0.69205(16) -0.18692(9) 0.0496(4) Uani 1 d . . .
H14 H -0.5993 -0.6329 -0.1729 0.059 Uiso 1 calc . . R
C15 C -0.9630(3) -0.47255(17) 0.11668(9) 0.0569(5) Uani 1 d . . .
H15 H -0.8296 -0.4731 0.1236 0.068 Uiso 1 calc . . R
C16 C -1.2794(4) -0.3975(2) 0.13255(11) 0.0687(6) Uani 1 d . . .
C17 C -0.8317(4) -0.86842(16) -0.22831(10) 0.0579(5) Uani 1 d . . .
H17 H -0.8903 -0.9276 -0.2424 0.070 Uiso 1 calc . . R
C18 C -1.3578(4) -0.4695(2) 0.09496(12) 0.0720(6) Uani 1 d . . .
H18 H -1.4905 -0.4674 0.0868 0.086 Uiso 1 calc . . R
C19 C -1.0813(4) -0.39972(19) 0.14288(11) 0.0701(6) Uani 1 d . . .
H19 H -1.0261 -0.3515 0.1679 0.084 Uiso 1 calc . . R
C20 C -0.5010(4) -0.33741(16) -0.05785(11) 0.0642(6) Uani 1 d . . .
H20 H -0.4186 -0.2825 -0.0651 0.077 Uiso 1 calc . . R
C21 C -0.5507(3) -0.76467(18) -0.21592(10) 0.0574(5) Uani 1 d . . .
H21 H -0.4179 -0.7543 -0.2212 0.069 Uiso 1 calc . . R
C22 C -1.4060(6) -0.3178(3) 0.16175(19) 0.1133(13) Uani 1 d . . .
H22A H -1.5335 -0.3191 0.1444 0.170 Uiso 1 calc . . GR
H22B H -1.3492 -0.2515 0.1562 0.170 Uiso 1 calc . . GR
H22C H -1.4157 -0.3322 0.2031 0.170 Uiso 1 calc . . GR
C23 C -0.6878(5) -0.32065(15) -0.03835(12) 0.0704(7) Uani 1 d . . .
H23 H -0.7308 -0.2542 -0.0320 0.084 Uiso 1 calc . . R
C24 C -1.2460(4) -0.54395(19) 0.06921(10) 0.0586(5) Uani 1 d . . .
H24 H -1.3023 -0.5931 0.0450 0.070 Uiso 1 calc . . R
C25 C -0.5142(5) -0.9308(2) -0.27000(12) 0.0819(8) Uani 1 d . . .
H25A H -0.5731 -0.9970 -0.2664 0.123 Uiso 1 calc . . GR
H25B H -0.3857 -0.9325 -0.2534 0.123 Uiso 1 calc . . GR
H25C H -0.5064 -0.9123 -0.3109 0.123 Uiso 1 calc . . GR
C26 C -0.4359(3) -0.43602(18) -0.06662(10) 0.0571(5) Uani 1 d . . .
H26 H -0.3090 -0.4476 -0.0792 0.068 Uiso 1 calc . . R


_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 O1 1.4316(14) . ?
S1 O7 1.4367(15) . ?
S1 C9 1.7664(17) . ?
S1 C11 1.7508(18) . ?
S2 O3 1.4335(16) . ?
S2 O4 1.4317(15) . ?
S2 C5 1.8043(16) . ?
S2 C6 1.7585(19) . ?
C2 C17 1.376(3) . ?
C2 C21 1.389(3) . ?
C2 C25 1.505(3) . ?
C5 C8 1.488(2) . ?
C5 C9 1.323(2) . ?
C6 C15 1.380(3) . ?
C6 C24 1.388(3) . ?
C8 C10 1.387(3) . ?
C8 C13 1.382(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C23 1.387(3) . ?
C11 C12 1.387(3) . ?
C11 C14 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C17 1.384(3) . ?
C13 H13 0.9300 . ?
C13 C26 1.382(3) . ?
C14 H14 0.9300 . ?
C14 C21 1.372(3) . ?
C15 H15 0.9300 . ?
C15 C19 1.387(3) . ?
C16 C18 1.380(4) . ?
C16 C19 1.381(4) . ?
C16 C22 1.511(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C24 1.372(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C23 1.375(4) . ?
C20 C26 1.381(3) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26 0.9300 . ?

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 S1 O7 119.25(10) . . ?
O1 S1 C9 110.24(8) . . ?
O1 S1 C11 109.06(9) . . ?
O7 S1 C9 105.03(9) . . ?
O7 S1 C11 108.44(9) . . ?
C11 S1 C9 103.68(8) . . ?
O3 S2 C5 107.26(9) . . ?
O3 S2 C6 108.67(9) . . ?
O4 S2 O3 119.36(10) . . ?
O4 S2 C5 107.84(8) . . ?
O4 S2 C6 109.17(10) . . ?
C6 S2 C5 103.36(8) . . ?
C17 C2 C21 118.5(2) . . ?
C17 C2 C25 121.3(2) . . ?
C21 C2 C25 120.2(2) . . ?
C8 C5 S2 116.41(12) . . ?
C9 C5 S2 114.83(13) . . ?
C9 C5 C8 128.70(15) . . ?
C15 C6 S2 120.15(16) . . ?
C15 C6 C24 121.1(2) . . ?
C24 C6 S2 118.77(16) . . ?
C10 C8 C5 121.09(18) . . ?
C13 C8 C5 119.20(15) . . ?
C13 C8 C10 119.71(18) . . ?
S1 C9 H9 117.1 . . ?
C5 C9 S1 125.87(13) . . ?
C5 C9 H9 117.1 . . ?
C8 C10 H10 120.2 . . ?
C8 C10 C23 119.5(2) . . ?
C23 C10 H10 120.2 . . ?
C12 C11 S1 120.05(15) . . ?
C14 C11 S1 119.26(15) . . ?
C14 C11 C12 120.67(18) . . ?
C11 C12 H12 120.5 . . ?
C17 C12 C11 118.93(19) . . ?
C17 C12 H12 120.5 . . ?
C8 C13 H13 119.8 . . ?
C26 C13 C8 120.32(18) . . ?
C26 C13 H13 119.8 . . ?
C11 C14 H14 120.5 . . ?
C21 C14 C11 119.08(19) . . ?
C21 C14 H14 120.5 . . ?
C6 C15 H15 120.6 . . ?
C6 C15 C19 118.8(2) . . ?
C19 C15 H15 120.6 . . ?
C18 C16 C19 118.3(2) . . ?
C18 C16 C22 121.2(3) . . ?
C19 C16 C22 120.5(3) . . ?
C2 C17 C12 121.3(2) . . ?
C2 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C16 C18 H18 119.0 . . ?
C24 C18 C16 122.0(2) . . ?
C24 C18 H18 119.0 . . ?
C15 C19 H19 119.4 . . ?
C16 C19 C15 121.3(2) . . ?
C16 C19 H19 119.4 . . ?
C23 C20 H20 120.1 . . ?
C23 C20 C26 119.84(19) . . ?
C26 C20 H20 120.1 . . ?
C2 C21 H21 119.3 . . ?
C14 C21 C2 121.5(2) . . ?
C14 C21 H21 119.3 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C10 C23 H23 119.7 . . ?
C20 C23 C10 120.6(2) . . ?
C20 C23 H23 119.7 . . ?
C6 C24 H24 120.7 . . ?
C18 C24 C6 118.5(2) . . ?
C18 C24 H24 120.7 . . ?
C2 C25 H25A 109.5 . . ?
C2 C25 H25B 109.5 . . ?
C2 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C13 C26 H26 120.0 . . ?
C20 C26 C13 120.0(2) . . ?
C20 C26 H26 120.0 . . ?

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
S1 C11 C12 C17 176.02(16) . . . . ?
S1 C11 C14 C21 -177.01(16) . . . . ?
S2 C5 C8 C10 -83.2(2) . . . . ?
S2 C5 C8 C13 96.77(17) . . . . ?
S2 C5 C9 S1 177.23(11) . . . . ?
S2 C6 C15 C19 179.22(18) . . . . ?
S2 C6 C24 C18 -177.92(19) . . . . ?
O1 S1 C9 C5 -8.05(19) . . . . ?
O1 S1 C11 C12 -149.86(15) . . . . ?
O1 S1 C11 C14 28.55(18) . . . . ?
O3 S2 C5 C8 -40.55(15) . . . . ?
O3 S2 C5 C9 136.89(14) . . . . ?
O3 S2 C6 C15 11.34(19) . . . . ?
O3 S2 C6 C24 -169.65(17) . . . . ?
O4 S2 C5 C8 -170.29(14) . . . . ?
O4 S2 C5 C9 7.15(17) . . . . ?
O4 S2 C6 C15 143.06(17) . . . . ?
O4 S2 C6 C24 -37.94(19) . . . . ?
C5 S2 C6 C15 -102.37(17) . . . . ?
C5 S2 C6 C24 76.64(18) . . . . ?
C5 C8 C10 C23 -178.2(2) . . . . ?
C5 C8 C13 C26 178.43(17) . . . . ?
C6 S2 C5 C8 74.18(14) . . . . ?
C6 S2 C5 C9 -108.38(14) . . . . ?
C6 C15 C19 C16 -0.6(4) . . . . ?
O7 S1 C9 C5 -137.71(17) . . . . ?
O7 S1 C11 C12 -18.55(18) . . . . ?
O7 S1 C11 C14 159.86(15) . . . . ?
C8 C5 C9 S1 -5.7(3) . . . . ?
C8 C10 C23 C20 -0.7(4) . . . . ?
C8 C13 C26 C20 0.2(3) . . . . ?
C9 S1 C11 C12 92.70(16) . . . . ?
C9 S1 C11 C14 -88.88(16) . . . . ?
C9 C5 C8 C10 99.8(2) . . . . ?
C9 C5 C8 C13 -80.3(2) . . . . ?
C10 C8 C13 C26 -1.6(3) . . . . ?
C11 S1 C9 C5 108.56(17) . . . . ?
C11 C12 C17 C2 1.5(3) . . . . ?
C11 C14 C21 C2 0.5(3) . . . . ?
C12 C11 C14 C21 1.4(3) . . . . ?
C13 C8 C10 C23 1.9(3) . . . . ?
C14 C11 C12 C17 -2.4(3) . . . . ?
C15 C6 C24 C18 1.1(4) . . . . ?
C16 C18 C24 C6 -2.1(4) . . . . ?
C17 C2 C21 C14 -1.3(3) . . . . ?
C18 C16 C19 C15 -0.4(4) . . . . ?
C19 C16 C18 C24 1.8(4) . . . . ?
C21 C2 C17 C12 0.3(3) . . . . ?
C22 C16 C18 C24 -178.3(3) . . . . ?
C22 C16 C19 C15 179.7(3) . . . . ?
C23 C20 C26 C13 1.0(4) . . . . ?
C24 C6 C15 C19 0.2(3) . . . . ?
C25 C2 C17 C12 179.9(2) . . . . ?
C25 C2 C21 C14 179.1(2) . . . . ?
C26 C20 C23 C10 -0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
