# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_LZQ-443
_database_code_depnum_ccdc_archive 'CCDC 1469553'
_audit_update_record             
;
2016-03-19 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 O2 S2'
_chemical_formula_weight         330.44

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'
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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.7723(14)
_cell_length_b                   5.6960(4)
_cell_length_c                   19.6942(15)
_cell_angle_alpha                90
_cell_angle_beta                 113.699(10)
_cell_angle_gamma                90
_cell_volume                     1722.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2005
_cell_measurement_theta_min      3.422
_cell_measurement_theta_max      26.306

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.313
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7944
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.045
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3362
_reflns_number_gt                2249
_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-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0426P)²+0.4137P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0160(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3362
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.003
_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 0.08736(4) 1.04912(14) 0.42264(4) 0.0808(3) Uani 1 1 d . . . . .
S2 S 0.10115(4) 0.80360(16) 0.29395(3) 0.0841(3) Uani 1 1 d . . . . .
O1 O 0.32582(12) 1.1012(3) 0.52730(10) 0.0872(6) Uani 1 1 d . . . . .
O2 O 0.29153(8) 0.7794(3) 0.40105(7) 0.0563(4) Uani 1 1 d . . . . .
C1 C 0.28836(16) 0.8872(5) 0.64000(13) 0.0691(7) Uani 1 1 d . . . . .
H1 H 0.3196 1.0269 0.6522 0.083 Uiso 1 1 calc R U . . .
C2 C 0.2732(2) 0.7643(6) 0.69367(14) 0.0870(9) Uani 1 1 d . . . . .
H2 H 0.2938 0.8220 0.7419 0.104 Uiso 1 1 calc R U . . .
C3 C 0.2282(2) 0.5581(6) 0.67646(16) 0.0897(9) Uani 1 1 d . . . . .
H3 H 0.2173 0.4767 0.7128 0.108 Uiso 1 1 calc R U . . .
C4 C 0.19869(17) 0.4701(5) 0.60555(16) 0.0808(8) Uani 1 1 d . . . . .
H4 H 0.1693 0.3275 0.5943 0.097 Uiso 1 1 calc R U . . .
C5 C 0.21275(15) 0.5933(4) 0.55129(13) 0.0634(6) Uani 1 1 d . . . . .
H5 H 0.1921 0.5342 0.5033 0.076 Uiso 1 1 calc R U . . .
C6 C 0.25722(13) 0.8039(4) 0.56747(11) 0.0533(5) Uani 1 1 d . . . . .
C7 C 0.27569(14) 0.9365(4) 0.51104(12) 0.0575(6) Uani 1 1 d . . . . .
C8 C 0.23610(13) 0.8579(4) 0.43092(11) 0.0531(5) Uani 1 1 d . . . . .
C9 C 0.15160(14) 0.8855(4) 0.38782(12) 0.0611(6) Uani 1 1 d . . . . .
C10 C 0.37071(16) 0.6660(6) 0.45117(13) 0.0862(9) Uani 1 1 d . . . . .
H10A H 0.3573 0.5521 0.4817 0.103 Uiso 1 1 calc R U . . .
H10B H 0.4103 0.7817 0.4835 0.103 Uiso 1 1 calc R U . . .
C11 C 0.41191(13) 0.5467(4) 0.40604(11) 0.0551(6) Uani 1 1 d . . . . .
C12 C 0.38173(16) 0.3334(5) 0.37262(16) 0.0789(8) Uani 1 1 d . . . . .
H12 H 0.3352 0.2604 0.3783 0.095 Uiso 1 1 calc R U . . .
C13 C 0.4209(2) 0.2277(5) 0.33043(18) 0.0963(10) Uani 1 1 d . . . . .
H13 H 0.3998 0.0853 0.3070 0.116 Uiso 1 1 calc R U . . .
C14 C 0.4901(2) 0.3317(6) 0.32316(14) 0.0895(9) Uani 1 1 d . . . . .
H14 H 0.5159 0.2606 0.2945 0.107 Uiso 1 1 calc R U . . .
C15 C 0.52115(16) 0.5365(5) 0.35719(14) 0.0736(7) Uani 1 1 d . . . . .
H15 H 0.5693 0.6049 0.3530 0.088 Uiso 1 1 calc R U . . .
C16 C 0.48223(14) 0.6455(4) 0.39805(12) 0.0585(6) Uani 1 1 d . . . . .
H16 H 0.5039 0.7886 0.4207 0.070 Uiso 1 1 calc R U . . .
C17 C 0.00501(17) 0.8407(7) 0.41745(17) 0.1097(11) Uani 1 1 d . . . . .
H17A H -0.0123 0.7535 0.3721 0.165 Uiso 1 1 calc R U . . .
H17B H -0.0445 0.9221 0.4187 0.165 Uiso 1 1 calc R U . . .
H17C H 0.0277 0.7349 0.4588 0.165 Uiso 1 1 calc R U . . .
C18 C 0.13598(18) 0.5057(6) 0.29467(16) 0.0954(9) Uani 1 1 d . . . . .
H18A H 0.1956 0.5036 0.3003 0.143 Uiso 1 1 calc R U . . .
H18B H 0.1001 0.4309 0.2488 0.143 Uiso 1 1 calc R U . . .
H18C H 0.1309 0.4230 0.3352 0.143 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 C9 1.759(2) . ?
S1 C17 1.793(3) . ?
S2 C9 1.759(2) . ?
S2 C18 1.793(3) . ?
O1 C7 1.214(3) . ?
O2 C8 1.360(2) . ?
O2 C10 1.450(3) . ?
C1 C2 1.373(4) . ?
C1 C6 1.392(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.476(3) . ?
C7 C8 1.513(3) . ?
C8 C9 1.337(3) . ?
C10 C11 1.491(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.371(3) . ?
C11 C12 1.378(4) . ?
C12 C13 1.386(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.360(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.342(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C9 S1 C17 101.87(14) . . ?
C9 S2 C18 103.02(13) . . ?
C8 O2 C10 116.76(16) . . ?
C2 C1 C6 120.5(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.5(2) . . ?
C5 C6 C7 121.90(19) . . ?
C1 C6 C7 119.5(2) . . ?
O1 C7 C6 122.0(2) . . ?
O1 C7 C8 118.1(2) . . ?
C6 C7 C8 119.80(18) . . ?
C9 C8 O2 119.90(19) . . ?
C9 C8 C7 122.4(2) . . ?
O2 C8 C7 117.30(17) . . ?
C8 C9 S2 125.14(18) . . ?
C8 C9 S1 118.29(18) . . ?
S2 C9 S1 116.05(12) . . ?
O2 C10 C11 108.32(17) . . ?
O2 C10 H10A 110.0 . . ?
C11 C10 H10A 110.0 . . ?
O2 C10 H10B 110.0 . . ?
C11 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C16 C11 C12 118.3(2) . . ?
C16 C11 C10 120.5(2) . . ?
C12 C11 C10 121.2(2) . . ?
C11 C12 C13 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 121.0(2) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
S1 C17 H17A 109.5 . . ?
S1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
S1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S2 C18 H18A 109.5 . . ?
S2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
S2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
C6 C1 C2 C3 0.6(4) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C5 C6 C7 178.1(2) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
C2 C1 C6 C7 -178.8(2) . . . . ?
C5 C6 C7 O1 -168.4(2) . . . . ?
C1 C6 C7 O1 8.9(3) . . . . ?
C5 C6 C7 C8 7.6(3) . . . . ?
C1 C6 C7 C8 -175.1(2) . . . . ?
C10 O2 C8 C9 -156.1(2) . . . . ?
C10 O2 C8 C7 30.6(3) . . . . ?
O1 C7 C8 C9 -111.2(3) . . . . ?
C6 C7 C8 C9 72.7(3) . . . . ?
O1 C7 C8 O2 61.9(3) . . . . ?
C6 C7 C8 O2 -114.2(2) . . . . ?
O2 C8 C9 S2 5.9(3) . . . . ?
C7 C8 C9 S2 178.85(17) . . . . ?
O2 C8 C9 S1 -165.47(15) . . . . ?
C7 C8 C9 S1 7.5(3) . . . . ?
C18 S2 C9 C8 50.7(2) . . . . ?
C18 S2 C9 S1 -137.77(15) . . . . ?
C17 S1 C9 C8 -122.0(2) . . . . ?
C17 S1 C9 S2 65.84(17) . . . . ?
C8 O2 C10 C11 167.4(2) . . . . ?
O2 C10 C11 C16 102.3(3) . . . . ?
O2 C10 C11 C12 -79.0(3) . . . . ?
C16 C11 C12 C13 -1.8(3) . . . . ?
C10 C11 C12 C13 179.4(2) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 -1.6(4) . . . . ?
C12 C11 C16 C15 0.7(3) . . . . ?
C10 C11 C16 C15 179.5(2) . . . . ?
C14 C15 C16 C11 1.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18C S1 0.96 3.01 3.928(3) 161.2 1_545
C18 H18A O2 0.96 2.54 3.039(3) 112.8 .
C17 H17A S2 0.96 2.90 3.423(3) 115.2 .
C10 H10B O1 0.97 2.65 3.141(4) 111.4 .

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.032

_shelxl_version_number           2013-4

