# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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 
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data_nelson12_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1536558'
_audit_update_record             
;
2017-03-07 deposited with the CCDC.
2017-04-10 downloaded from the CCDC.
;
_audit_creation_date             2016-12-01
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C46 H62 O6 S2'
_chemical_formula_sum            'C46 H62 O6 S2'
_chemical_formula_weight         775.07
_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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.9364(3)
_cell_length_b                   7.6637(2)
_cell_length_c                   18.4671(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.5930(10)
_cell_angle_gamma                90
_cell_volume                     2095.36(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7833
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.61
_cell_measurement_theta_min      2.985
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.658
_exptl_absorpt_coefficient_mu    1.521
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0853 before and 0.0641 after correction.
The Ratio of minimum to maximum transmission is 0.8019.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17378
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.609
_diffrn_reflns_theta_min         2.985
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3356
_reflns_number_total             3784
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+1.1774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0975
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C8(H8A,H8B), C10(H10A,H10B), C6(H6A,H6B),
 C7(H7A,H7B), C5(H5A,H5B), C9(H9A,H9B), C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C19(H19), C23(H23), C21(H21), C20(H20), C22(H22)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.51206(2) 0.19738(5) 0.11282(2) 0.01183(12) Uani 1 1 d . . . . .
O3 O 0.65045(7) 0.50629(15) 0.10754(6) 0.0143(3) Uani 1 1 d . . . . .
O2 O 0.48931(8) 0.26276(15) 0.18113(6) 0.0170(3) Uani 1 1 d . . . . .
O1 O 0.58952(8) 0.08601(15) 0.11470(6) 0.0175(3) Uani 1 1 d . . . . .
C13 C 0.57526(11) 0.5102(2) 0.05683(9) 0.0122(3) Uani 1 1 d . . . . .
C14 C 0.51424(11) 0.3732(2) 0.05060(9) 0.0128(3) Uani 1 1 d . . . . .
C16 C 0.38656(11) 0.2017(2) 0.00328(9) 0.0135(3) Uani 1 1 d . . . . .
H16 H 0.3348 0.1741 -0.0304 0.016 Uiso 1 1 calc R . . . .
C15 C 0.44033(11) 0.3584(2) -0.00401(9) 0.0128(3) Uani 1 1 d . . . . .
C18 C 0.38196(11) -0.0702(2) 0.08196(9) 0.0138(3) Uani 1 1 d . . . . .
C17 C 0.41504(11) 0.0990(2) 0.06071(9) 0.0133(3) Uani 1 1 d . . . . .
C19 C 0.31712(11) -0.1592(2) 0.03396(9) 0.0162(3) Uani 1 1 d . . . . .
H19 H 0.2938 -0.1072 -0.0113 0.019 Uiso 1 1 calc R . . . .
C11 C 0.73379(11) 0.5716(2) 0.22250(9) 0.0170(4) Uani 1 1 d . . . . .
H11A H 0.7863 0.5870 0.1955 0.020 Uiso 1 1 calc R . . . .
H11B H 0.7323 0.4480 0.2378 0.020 Uiso 1 1 calc R . . . .
C12 C 0.64839(11) 0.6130(2) 0.17232(9) 0.0154(3) Uani 1 1 d . . . . .
H12A H 0.5946 0.5846 0.1962 0.018 Uiso 1 1 calc R . . . .
H12B H 0.6463 0.7384 0.1593 0.018 Uiso 1 1 calc R . . . .
C8 C 0.83920(11) 0.7502(2) 0.41332(9) 0.0172(4) Uani 1 1 d . . . . .
H8A H 0.8464 0.8726 0.3979 0.021 Uiso 1 1 calc R . . . .
H8B H 0.7836 0.7441 0.4371 0.021 Uiso 1 1 calc R . . . .
C10 C 0.74588(11) 0.6877(2) 0.29024(9) 0.0161(3) Uani 1 1 d . . . . .
H10A H 0.6904 0.6821 0.3142 0.019 Uiso 1 1 calc R . . . .
H10B H 0.7538 0.8100 0.2751 0.019 Uiso 1 1 calc R . . . .
C23 C 0.41507(11) -0.1486(2) 0.14878(9) 0.0164(4) Uani 1 1 d . . . . .
H23 H 0.4585 -0.0893 0.1822 0.020 Uiso 1 1 calc R . . . .
C21 C 0.32134(12) -0.3994(2) 0.11772(10) 0.0204(4) Uani 1 1 d . . . . .
H21 H 0.3015 -0.5124 0.1295 0.024 Uiso 1 1 calc R . . . .
C6 C 0.92703(12) 0.8174(2) 0.53732(9) 0.0190(4) Uani 1 1 d . . . . .
H6A H 0.8718 0.8026 0.5610 0.023 Uiso 1 1 calc R . . . .
H6B H 0.9299 0.9409 0.5221 0.023 Uiso 1 1 calc R . . . .
C7 C 0.91970(12) 0.7020(2) 0.46952(9) 0.0191(4) Uani 1 1 d . . . . .
H7A H 0.9138 0.5788 0.4842 0.023 Uiso 1 1 calc R . . . .
H7B H 0.9759 0.7128 0.4468 0.023 Uiso 1 1 calc R . . . .
C5 C 1.00927(12) 0.7772(2) 0.59304(9) 0.0181(4) Uani 1 1 d . . . . .
H5A H 1.0646 0.7981 0.5702 0.022 Uiso 1 1 calc R . . . .
H5B H 1.0081 0.6521 0.6063 0.022 Uiso 1 1 calc R . . . .
C20 C 0.28671(12) -0.3220(2) 0.05183(10) 0.0198(4) Uani 1 1 d . . . . .
H20 H 0.2423 -0.3809 0.0192 0.024 Uiso 1 1 calc R . . . .
C9 C 0.82673(12) 0.6350(2) 0.34533(9) 0.0188(4) Uani 1 1 d . . . . .
H9A H 0.8188 0.5125 0.3603 0.023 Uiso 1 1 calc R . . . .
H9B H 0.8821 0.6406 0.3213 0.023 Uiso 1 1 calc R . . . .
C4 C 1.01390(11) 0.8863(2) 0.66257(9) 0.0187(4) Uani 1 1 d . . . . .
H4A H 1.0183 1.0111 0.6496 0.022 Uiso 1 1 calc R . . . .
H4B H 0.9570 0.8705 0.6839 0.022 Uiso 1 1 calc R . . . .
C22 C 0.38462(12) -0.3126(2) 0.16633(10) 0.0207(4) Uani 1 1 d . . . . .
H22 H 0.4072 -0.3652 0.2117 0.025 Uiso 1 1 calc R . . . .
C3 C 1.09323(12) 0.8402(2) 0.72016(9) 0.0197(4) Uani 1 1 d . . . . .
H3A H 1.0891 0.7155 0.7333 0.024 Uiso 1 1 calc R . . . .
H3B H 1.1503 0.8569 0.6991 0.024 Uiso 1 1 calc R . . . .
C2 C 1.09604(13) 0.9504(3) 0.78910(10) 0.0258(4) Uani 1 1 d . . . . .
H2A H 1.1022 1.0747 0.7760 0.031 Uiso 1 1 calc R . . . .
H2B H 1.0379 0.9371 0.8088 0.031 Uiso 1 1 calc R . . . .
C1 C 1.17240(16) 0.9030(4) 0.84844(12) 0.0455(6) Uani 1 1 d . . . . .
H1A H 1.2303 0.9153 0.8294 0.068 Uiso 1 1 calc GR . . . .
H1B H 1.1650 0.7821 0.8639 0.068 Uiso 1 1 calc GR . . . .
H1C H 1.1712 0.9811 0.8903 0.068 Uiso 1 1 calc GR . . . .


_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 O2 1.4391(12) . ?
S1 O1 1.4345(12) . ?
S1 C14 1.7741(16) . ?
S1 C17 1.7962(16) . ?
O3 C13 1.3642(19) . ?
O3 C12 1.4525(19) . ?
C13 C14 1.385(2) . ?
C13 C15 1.400(2) 3_665 ?
C14 C15 1.398(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.461(2) . ?
C16 C17 1.344(2) . ?
C15 C13 1.400(2) 3_665 ?
C18 C17 1.460(2) . ?
C18 C19 1.401(2) . ?
C18 C23 1.402(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.508(2) . ?
C11 C10 1.526(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.526(2) . ?
C8 C9 1.526(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.527(2) . ?
C23 H23 0.9500 . ?
C23 C22 1.390(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.390(3) . ?
C21 C22 1.384(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.525(2) . ?
C6 C5 1.526(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.526(2) . ?
C20 H20 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.525(2) . ?
C22 H22 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.523(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.518(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

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
O2 S1 C14 109.26(7) . . ?
O2 S1 C17 110.40(7) . . ?
O1 S1 O2 117.98(7) . . ?
O1 S1 C14 112.57(7) . . ?
O1 S1 C17 110.75(7) . . ?
C14 S1 C17 93.12(8) . . ?
C13 O3 C12 116.61(12) . . ?
O3 C13 C14 120.91(14) . . ?
O3 C13 C15 122.68(14) . 3_665 ?
C14 C13 C15 116.11(15) . 3_665 ?
C13 C14 S1 126.16(13) . . ?
C13 C14 C15 124.74(15) . . ?
C15 C14 S1 108.97(12) . . ?
C15 C16 H16 122.1 . . ?
C17 C16 H16 122.1 . . ?
C17 C16 C15 115.70(14) . . ?
C13 C15 C16 127.79(15) 3_665 . ?
C14 C15 C13 119.14(15) . 3_665 ?
C14 C15 C16 113.05(14) . . ?
C19 C18 C17 119.52(15) . . ?
C19 C18 C23 118.83(15) . . ?
C23 C18 C17 121.63(15) . . ?
C16 C17 S1 109.01(12) . . ?
C16 C17 C18 130.49(15) . . ?
C18 C17 S1 120.44(12) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.66(16) . . ?
C20 C19 H19 119.7 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C12 C11 C10 112.35(14) . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
O3 C12 C11 106.24(13) . . ?
O3 C12 H12A 110.5 . . ?
O3 C12 H12B 110.5 . . ?
C11 C12 H12A 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C7 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C7 C8 C9 114.77(14) . . ?
C9 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C11 C10 C9 112.91(14) . . ?
H10A C10 H10B 107.8 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.30(16) . . ?
C22 C23 H23 119.9 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C22 C21 C20 120.39(16) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C7 C6 C5 113.64(14) . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
C6 C7 C8 112.51(14) . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C6 C5 C4 113.57(14) . . ?
H5A C5 H5B 107.7 . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C19 C20 C21 119.84(16) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C8 C9 C10 113.24(14) . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C3 C4 C5 113.85(14) . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 C23 119.97(16) . . ?
C21 C22 H22 120.0 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C2 C3 C4 112.79(15) . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C1 C2 C3 113.96(16) . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
