# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_Quest15mz002_0m
_audit_block_doi                 10.5517/cc1j0zl3
_database_code_depnum_ccdc_archive 'CCDC 1401125'
_audit_update_record             
;
2015-05-15 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H20 O4 S8'
_chemical_formula_weight         821.04

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                   3.9761(2)
_cell_length_b                   20.6573(11)
_cell_length_c                   9.8948(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.5712(18)
_cell_angle_gamma                90
_cell_volume                     807.37(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7874
_cell_measurement_theta_min      2.2945
_cell_measurement_theta_max      36.3080

_exptl_crystal_description       rod
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.602
_shelx_estimated_absorpt_T_min   0.773
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6454
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   'Apex2 v2014.1-1 (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10104
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.295
_diffrn_reflns_theta_max         36.308
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3740
_reflns_number_gt                3360
_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       'Apex2 v2014.1-1 (Bruker, 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2014/7 (Sheldrick, 2014), 
SHELXLE Rev656 (Hübschle et al., 2011)
;
_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)+(0.0361P)²+0.5085P] 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         3740
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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_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
C1 C 0.9499(2) 0.01146(5) 0.63559(10) 0.00852(15) Uani 1 1 d . . . . .
C2 C 0.8408(2) 0.05776(4) 0.53680(10) 0.00840(15) Uani 1 1 d . . . . .
C3 C 0.8869(2) 0.04560(5) 0.40000(10) 0.00855(15) Uani 1 1 d . . . . .
C4 C 0.7579(3) 0.09178(5) 0.29105(11) 0.01143(17) Uani 1 1 d . . . . .
H4 H 0.8741 0.0949 0.2126 0.014 Uiso 1 1 calc R U . . .
C5 C 0.9995(3) 0.10394(5) 0.83364(10) 0.00959(16) Uani 1 1 d . . . . .
C6 C 0.8955(3) 0.15063(5) 0.73617(10) 0.00956(16) Uani 1 1 d . . . . .
C7 C 0.9820(3) 0.21540(5) 0.76094(11) 0.01233(17) Uani 1 1 d . . . . .
H7 H 0.9169 0.2473 0.6939 0.015 Uiso 1 1 calc R U . . .
C8 C 1.1634(3) 0.23321(5) 0.88372(12) 0.01427(18) Uani 1 1 d . . . . .
H8 H 1.2145 0.2775 0.9019 0.017 Uiso 1 1 calc R U . . .
C9 C 1.2704(3) 0.18618(5) 0.98027(12) 0.01379(18) Uani 1 1 d . . . . .
H9 H 1.3957 0.1985 1.0639 0.017 Uiso 1 1 calc R U . . .
C10 C 1.1941(3) 0.12131(5) 0.95434(11) 0.01179(17) Uani 1 1 d . . . . .
H10 H 1.2742 0.0890 1.0185 0.014 Uiso 1 1 calc R U . . .
O1 O 0.5112(2) 0.12567(4) 0.29765(9) 0.01529(15) Uani 1 1 d . . . . .
S1 S 0.87101(7) 0.02287(2) 0.80659(3) 0.01073(6) Uani 1 1 d . . . . .
S2 S 0.64714(6) 0.13042(2) 0.58269(3) 0.01042(6) 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 C2 1.4005(14) . ?
C1 C3 1.4094(14) 3_756 ?
C1 S1 1.7715(10) . ?
C2 C3 1.4093(14) . ?
C2 S2 1.7698(10) . ?
C3 C1 1.4094(14) 3_756 ?
C3 C4 1.4862(14) . ?
C4 O1 1.2130(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.3929(14) . ?
C5 C10 1.3937(15) . ?
C5 S1 1.7623(10) . ?
C6 C7 1.3962(14) . ?
C6 S2 1.7643(10) . ?
C7 C8 1.3895(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3945(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.3914(15) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

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
C2 C1 C3 120.76(9) . 3_756 ?
C2 C1 S1 120.08(7) . . ?
C3 C1 S1 119.13(7) 3_756 . ?
C1 C2 C3 118.99(9) . . ?
C1 C2 S2 120.61(8) . . ?
C3 C2 S2 120.40(7) . . ?
C2 C3 C1 120.22(9) . 3_756 ?
C2 C3 C4 120.67(9) . . ?
C1 C3 C4 119.09(9) 3_756 . ?
O1 C4 C3 123.07(10) . . ?
O1 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
C6 C5 C10 120.44(9) . . ?
C6 C5 S1 119.67(8) . . ?
C10 C5 S1 119.85(8) . . ?
C5 C6 C7 119.64(9) . . ?
C5 C6 S2 121.64(8) . . ?
C7 C6 S2 118.70(8) . . ?
C8 C7 C6 120.00(10) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.11(10) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.11(10) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C5 119.60(10) . . ?
C9 C10 H10 120.2 . . ?
C5 C10 H10 120.2 . . ?
C5 S1 C1 101.04(5) . . ?
C6 S2 C2 101.79(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
C3 C1 C2 C3 1.97(16) 3_756 . . . ?
S1 C1 C2 C3 -175.91(7) . . . . ?
C3 C1 C2 S2 -178.14(7) 3_756 . . . ?
S1 C1 C2 S2 3.98(12) . . . . ?
C1 C2 C3 C1 -1.96(16) . . . 3_756 ?
S2 C2 C3 C1 178.15(7) . . . 3_756 ?
C1 C2 C3 C4 176.63(9) . . . . ?
S2 C2 C3 C4 -3.26(13) . . . . ?
C2 C3 C4 O1 -29.39(15) . . . . ?
C1 C3 C4 O1 149.21(10) 3_756 . . . ?
C10 C5 C6 C7 -1.20(16) . . . . ?
S1 C5 C6 C7 176.54(8) . . . . ?
C10 C5 C6 S2 -179.66(8) . . . . ?
S1 C5 C6 S2 -1.92(13) . . . . ?
C5 C6 C7 C8 -1.63(16) . . . . ?
S2 C6 C7 C8 176.87(9) . . . . ?
C6 C7 C8 C9 2.44(17) . . . . ?
C7 C8 C9 C10 -0.42(18) . . . . ?
C8 C9 C10 C5 -2.39(17) . . . . ?
C6 C5 C10 C9 3.21(16) . . . . ?
S1 C5 C10 C9 -174.53(9) . . . . ?
C6 C5 S1 C1 45.93(9) . . . . ?
C10 C5 S1 C1 -136.32(9) . . . . ?
C2 C1 S1 C5 -47.14(9) . . . . ?
C3 C1 S1 C5 134.95(8) 3_756 . . . ?
C5 C6 S2 C2 -41.91(10) . . . . ?
C7 C6 S2 C2 139.62(9) . . . . ?
C1 C2 S2 C6 40.41(9) . . . . ?
C3 C2 S2 C6 -139.70(8) . . . . ?

_refine_diff_density_max         0.630
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.089



