# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_lc62dec17_0m
_database_code_depnum_ccdc_archive 'CCDC 1029034'
_audit_update_record             
;
2014-10-13 deposited with the CCDC.
2015-02-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H64 O4 S2'
_chemical_formula_weight         372.55

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'

_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                   8.972(3)
_cell_length_b                   17.266(4)
_cell_length_c                   14.260(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.66(3)
_cell_angle_gamma                90.00
_cell_volume                     2201.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    1.393
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4958
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_sigmaI/netI    0.0909
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.03
_diffrn_reflns_theta_max         50.04
_reflns_number_total             2115
_reflns_number_gt                1316
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1280P)²+2.9782P] 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     SHELXL
_refine_ls_extinction_coef       0.0006(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2115
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0842
_refine_ls_wR_factor_ref         0.2643
_refine_ls_wR_factor_gt          0.2290
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_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
S1 S 0.0799(2) 1.07684(13) 0.88985(14) 0.0683(9) Uani 1 1 d . . .
O1 O 0.1970(6) 0.8960(3) 1.0391(4) 0.0813(18) Uani 1 1 d . . .
O2 O 0.5364(6) 1.1666(4) 0.5688(4) 0.096(2) Uani 1 1 d . . .
C18 C 0.1128(9) 1.2664(6) 0.6434(7) 0.109(4) Uani 1 1 d . . .
H19 H 0.0758 1.3109 0.6085 0.163 Uiso 1 1 calc R . .
H21 H 0.1310 1.2799 0.7087 0.163 Uiso 1 1 calc R . .
H20 H 0.0401 1.2256 0.6369 0.163 Uiso 1 1 calc R . .
C15 C 0.2583(8) 1.2392(5) 0.6057(6) 0.071(2) Uani 1 1 d . . .
C9 C 0.3291(8) 1.1708(5) 0.6608(6) 0.063(2) Uani 1 1 d . . .
C10 C 0.2673(8) 1.1389(5) 0.7349(6) 0.068(2) Uani 1 1 d . . .
H3 H 0.1787 1.1603 0.7527 0.081 Uiso 1 1 calc R . .
C5 C 0.3286(8) 1.0744(5) 0.7881(6) 0.065(2) Uani 1 1 d . . .
C4 C 0.2529(8) 1.0409(5) 0.8608(6) 0.064(2) Uani 1 1 d . . .
C1 C 0.0629(8) 1.0029(4) 0.9737(5) 0.055(2) Uani 1 1 d . . .
C2 C 0.1920(9) 0.9550(5) 0.9777(6) 0.067(2) Uani 1 1 d . . .
C19 C 0.3247(6) 0.8452(4) 1.0370(4) 0.096(3) Uani 1 1 d . . .
H22 H 0.4150 0.8763 1.0433 0.116 Uiso 1 1 calc R . .
H23 H 0.3207 0.8199 0.9761 0.116 Uiso 1 1 calc R . .
C20 C 0.3347(6) 0.7833(4) 1.1135(4) 0.124(4) Uani 1 1 d R . .
H24 H 0.4256 0.7534 1.1099 0.149 Uiso 1 1 d R . .
H25 H 0.3385 0.8077 1.1749 0.149 Uiso 1 1 d R . .
C21 C 0.2106(6) 0.7344(4) 1.1021(4) 0.122(4) Uani 1 1 d R . .
H26 H 0.1988 0.7142 1.0384 0.147 Uiso 1 1 calc R . .
H27 H 0.1203 0.7620 1.1147 0.147 Uiso 1 1 calc R . .
C22 C 0.2447(6) 0.6606(4) 1.1812(4) 0.166(5) Uani 1 1 d R . .
H28 H 0.3405 0.6368 1.1722 0.199 Uiso 1 1 d R . .
H29 H 0.2481 0.6807 1.2448 0.199 Uiso 1 1 d R . .
C23 C 0.1294(16) 0.6043(9) 1.1672(11) 0.185(6) Uani 1 1 d . . .
H32 H 0.0474 0.6256 1.1281 0.277 Uiso 1 1 calc R . .
H31 H 0.0956 0.5897 1.2269 0.277 Uiso 1 1 calc R . .
H30 H 0.1674 0.5595 1.1372 0.277 Uiso 1 1 calc R . .
C13 C 0.8123(8) 1.1041(6) 0.6694(6) 0.088(3) Uani 1 1 d . . .
H7 H 0.7784 1.1450 0.6274 0.132 Uiso 1 1 calc R . .
H9 H 0.9046 1.0835 0.6504 0.132 Uiso 1 1 calc R . .
H8 H 0.8279 1.1241 0.7323 0.132 Uiso 1 1 calc R . .
C11 C 0.6943(8) 1.0397(5) 0.6666(6) 0.072(2) Uani 1 1 d . . .
C12 C 0.7469(10) 0.9749(6) 0.7343(8) 0.118(4) Uani 1 1 d . . .
H5 H 0.7552 0.9944 0.7975 0.177 Uiso 1 1 calc R . .
H6 H 0.8427 0.9564 0.7186 0.177 Uiso 1 1 calc R . .
H4 H 0.6760 0.9332 0.7292 0.177 Uiso 1 1 calc R . .
C7 C 0.5427(8) 1.0733(5) 0.6900(6) 0.064(2) Uani 1 1 d . . .
C8 C 0.4742(9) 1.1399(5) 0.6369(6) 0.071(2) Uani 1 1 d . . .
C6 C 0.4680(8) 1.0444(5) 0.7629(6) 0.074(3) Uani 1 1 d . . .
H2 H 0.5105 1.0032 0.7975 0.089 Uiso 1 1 calc R . .
C3 C 0.2952(8) 0.9759(5) 0.9172(6) 0.068(2) Uani 1 1 d . . .
H1 H 0.3851 0.9498 0.9135 0.082 Uiso 1 1 calc R . .
C14 C 0.6800(10) 1.0046(6) 0.5661(7) 0.110(4) Uani 1 1 d . . .
H11 H 0.6451 1.0436 0.5216 0.165 Uiso 1 1 calc R . .
H12 H 0.6102 0.9624 0.5638 0.165 Uiso 1 1 calc R . .
H10 H 0.7759 0.9860 0.5507 0.165 Uiso 1 1 calc R . .
C16 C 0.3645(10) 1.3091(5) 0.6093(7) 0.103(3) Uani 1 1 d . . .
H15 H 0.3182 1.3510 0.5734 0.155 Uiso 1 1 calc R . .
H14 H 0.4560 1.2949 0.5833 0.155 Uiso 1 1 calc R . .
H13 H 0.3856 1.3252 0.6735 0.155 Uiso 1 1 calc R . .
C17 C 0.2229(11) 1.2145(6) 0.5026(7) 0.117(4) Uani 1 1 d . . .
H16 H 0.3143 1.2101 0.4724 0.175 Uiso 1 1 calc R . .
H17 H 0.1597 1.2526 0.4706 0.175 Uiso 1 1 calc R . .
H18 H 0.1726 1.1654 0.5006 0.175 Uiso 1 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 C4 1.753(7) . ?
S1 C1 1.764(7) . ?
O1 C2 1.341(9) . ?
O1 C19 1.446(7) . ?
O2 C8 1.247(9) . ?
C18 C15 1.526(10) . ?
C18 H19 0.9600 . ?
C18 H21 0.9600 . ?
C18 H20 0.9600 . ?
C15 C9 1.527(11) . ?
C15 C16 1.537(11) . ?
C15 C17 1.539(11) . ?
C9 C10 1.350(10) . ?
C9 C8 1.472(11) . ?
C10 C5 1.432(10) . ?
C10 H3 0.9300 . ?
C5 C4 1.408(10) . ?
C5 C6 1.426(10) . ?
C4 C3 1.414(10) . ?
C1 C1 1.409(14) 3_577 ?
C1 C2 1.420(10) . ?
C2 C3 1.364(10) . ?
C19 C20 1.5248 . ?
C19 H22 0.9700 . ?
C19 H23 0.9700 . ?
C20 C21 1.3971 . ?
C20 H24 0.9700 . ?
C20 H25 0.9700 . ?
C21 C22 1.7119 . ?
C21 H26 0.9700 . ?
C21 H27 0.9700 . ?
C22 C23 1.422(14) . ?
C22 H28 0.9700 . ?
C22 H29 0.9700 . ?
C23 H32 0.9600 . ?
C23 H31 0.9600 . ?
C23 H30 0.9600 . ?
C13 C11 1.534(11) . ?
C13 H7 0.9600 . ?
C13 H9 0.9600 . ?
C13 H8 0.9600 . ?
C11 C12 1.528(11) . ?
C11 C7 1.540(10) . ?
C11 C14 1.552(11) . ?
C12 H5 0.9600 . ?
C12 H6 0.9600 . ?
C12 H4 0.9600 . ?
C7 C6 1.376(10) . ?
C7 C8 1.482(11) . ?
C6 H2 0.9300 . ?
C3 H1 0.9300 . ?
C14 H11 0.9600 . ?
C14 H12 0.9600 . ?
C14 H10 0.9600 . ?
C16 H15 0.9600 . ?
C16 H14 0.9600 . ?
C16 H13 0.9600 . ?
C17 H16 0.9600 . ?
C17 H17 0.9600 . ?
C17 H18 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
C4 S1 C1 91.8(4) . . ?
C2 O1 C19 115.6(6) . . ?
C15 C18 H19 109.5 . . ?
C15 C18 H21 109.5 . . ?
H19 C18 H21 109.5 . . ?
C15 C18 H20 109.5 . . ?
H19 C18 H20 109.5 . . ?
H21 C18 H20 109.5 . . ?
C18 C15 C9 112.9(7) . . ?
C18 C15 C16 107.0(7) . . ?
C9 C15 C16 111.1(7) . . ?
C18 C15 C17 107.8(8) . . ?
C9 C15 C17 108.8(7) . . ?
C16 C15 C17 109.2(8) . . ?
C10 C9 C8 117.4(8) . . ?
C10 C9 C15 122.5(7) . . ?
C8 C9 C15 120.0(7) . . ?
C9 C10 C5 124.6(7) . . ?
C9 C10 H3 117.7 . . ?
C5 C10 H3 117.7 . . ?
C4 C5 C6 121.4(8) . . ?
C4 C5 C10 121.5(7) . . ?
C6 C5 C10 117.1(7) . . ?
C5 C4 C3 128.5(7) . . ?
C5 C4 S1 121.2(7) . . ?
C3 C4 S1 110.3(6) . . ?
C1 C1 C2 128.6(8) 3_577 . ?
C1 C1 S1 122.0(8) 3_577 . ?
C2 C1 S1 109.5(5) . . ?
O1 C2 C3 128.7(8) . . ?
O1 C2 C1 116.9(7) . . ?
C3 C2 C1 114.5(8) . . ?
O1 C19 C20 114.3(3) . . ?
O1 C19 H22 108.7 . . ?
C20 C19 H22 108.7 . . ?
O1 C19 H23 108.7 . . ?
C20 C19 H23 108.7 . . ?
H22 C19 H23 107.6 . . ?
C21 C20 C19 109.9 . . ?
C21 C20 H24 109.7 . . ?
C19 C20 H24 109.7 . . ?
C21 C20 H25 109.7 . . ?
C19 C20 H25 109.7 . . ?
H24 C20 H25 108.2 . . ?
C20 C21 C22 106.0 . . ?
C20 C21 H26 110.5 . . ?
C22 C21 H26 110.5 . . ?
C20 C21 H27 110.5 . . ?
C22 C21 H27 110.5 . . ?
H26 C21 H27 108.7 . . ?
C23 C22 C21 109.1(6) . . ?
C23 C22 H28 109.5 . . ?
C21 C22 H28 109.9 . . ?
C23 C22 H29 110.0 . . ?
C21 C22 H29 109.9 . . ?
H28 C22 H29 108.3 . . ?
C22 C23 H32 109.5 . . ?
C22 C23 H31 109.5 . . ?
H32 C23 H31 109.5 . . ?
C22 C23 H30 109.5 . . ?
H32 C23 H30 109.5 . . ?
H31 C23 H30 109.5 . . ?
C11 C13 H7 109.5 . . ?
C11 C13 H9 109.5 . . ?
H7 C13 H9 109.5 . . ?
C11 C13 H8 109.5 . . ?
H7 C13 H8 109.5 . . ?
H9 C13 H8 109.5 . . ?
C12 C11 C13 109.7(7) . . ?
C12 C11 C7 111.8(7) . . ?
C13 C11 C7 110.0(7) . . ?
C12 C11 C14 107.2(8) . . ?
C13 C11 C14 108.3(7) . . ?
C7 C11 C14 109.8(7) . . ?
C11 C12 H5 109.5 . . ?
C11 C12 H6 109.5 . . ?
H5 C12 H6 109.5 . . ?
C11 C12 H4 109.5 . . ?
H5 C12 H4 109.5 . . ?
H6 C12 H4 109.5 . . ?
C6 C7 C8 117.4(7) . . ?
C6 C7 C11 121.3(8) . . ?
C8 C7 C11 121.2(7) . . ?
O2 C8 C9 120.4(9) . . ?
O2 C8 C7 119.4(7) . . ?
C9 C8 C7 120.1(8) . . ?
C7 C6 C5 123.3(8) . . ?
C7 C6 H2 118.3 . . ?
C5 C6 H2 118.3 . . ?
C2 C3 C4 113.9(7) . . ?
C2 C3 H1 123.0 . . ?
C4 C3 H1 123.0 . . ?
C11 C14 H11 109.5 . . ?
C11 C14 H12 109.5 . . ?
H11 C14 H12 109.5 . . ?
C11 C14 H10 109.5 . . ?
H11 C14 H10 109.5 . . ?
H12 C14 H10 109.5 . . ?
C15 C16 H15 109.5 . . ?
C15 C16 H14 109.5 . . ?
H15 C16 H14 109.5 . . ?
C15 C16 H13 109.5 . . ?
H15 C16 H13 109.5 . . ?
H14 C16 H13 109.5 . . ?
C15 C17 H16 109.5 . . ?
C15 C17 H17 109.5 . . ?
H16 C17 H17 109.5 . . ?
C15 C17 H18 109.5 . . ?
H16 C17 H18 109.5 . . ?
H17 C17 H18 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
C18 C15 C9 C10 0.0(12) . . . . ?
C16 C15 C9 C10 120.1(9) . . . . ?
C17 C15 C9 C10 -119.6(9) . . . . ?
C18 C15 C9 C8 -176.8(8) . . . . ?
C16 C15 C9 C8 -56.7(10) . . . . ?
C17 C15 C9 C8 63.6(10) . . . . ?
C8 C9 C10 C5 -3.8(12) . . . . ?
C15 C9 C10 C5 179.3(7) . . . . ?
C9 C10 C5 C4 -175.9(8) . . . . ?
C9 C10 C5 C6 2.8(12) . . . . ?
C6 C5 C4 C3 -1.0(13) . . . . ?
C10 C5 C4 C3 177.6(8) . . . . ?
C6 C5 C4 S1 -178.8(6) . . . . ?
C10 C5 C4 S1 -0.1(11) . . . . ?
C1 S1 C4 C5 176.1(7) . . . . ?
C1 S1 C4 C3 -2.0(6) . . . . ?
C4 S1 C1 C1 -179.1(8) . . . 3_577 ?
C4 S1 C1 C2 1.5(6) . . . . ?
C19 O1 C2 C3 -4.0(12) . . . . ?
C19 O1 C2 C1 175.9(6) . . . . ?
C1 C1 C2 O1 0.1(14) 3_577 . . . ?
S1 C1 C2 O1 179.5(6) . . . . ?
C1 C1 C2 C3 180.0(9) 3_577 . . . ?
S1 C1 C2 C3 -0.6(9) . . . . ?
C2 O1 C19 C20 174.6(5) . . . . ?
O1 C19 C20 C21 62.5(4) . . . . ?
C19 C20 C21 C22 172.4 . . . . ?
C20 C21 C22 C23 -174.3(8) . . . . ?
C12 C11 C7 C6 -1.4(11) . . . . ?
C13 C11 C7 C6 -123.5(9) . . . . ?
C14 C11 C7 C6 117.4(9) . . . . ?
C12 C11 C7 C8 176.4(8) . . . . ?
C13 C11 C7 C8 54.3(10) . . . . ?
C14 C11 C7 C8 -64.7(10) . . . . ?
C10 C9 C8 O2 179.4(8) . . . . ?
C15 C9 C8 O2 -3.7(12) . . . . ?
C10 C9 C8 C7 3.4(12) . . . . ?
C15 C9 C8 C7 -179.7(7) . . . . ?
C6 C7 C8 O2 -178.1(8) . . . . ?
C11 C7 C8 O2 3.9(12) . . . . ?
C6 C7 C8 C9 -2.1(11) . . . . ?
C11 C7 C8 C9 180.0(7) . . . . ?
C8 C7 C6 C5 1.1(12) . . . . ?
C11 C7 C6 C5 179.0(7) . . . . ?
C4 C5 C6 C7 177.3(8) . . . . ?
C10 C5 C6 C7 -1.3(12) . . . . ?
O1 C2 C3 C4 179.0(8) . . . . ?
C1 C2 C3 C4 -0.9(11) . . . . ?
C5 C4 C3 C2 -175.9(8) . . . . ?
S1 C4 C3 C2 2.0(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        50.04
_diffrn_measured_fraction_theta_full 0.934
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.061
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
