# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_141239lt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1836546'
_audit_update_record             
;
2018-04-12 deposited with the CCDC.
2018-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H52 S2'
_chemical_formula_weight         620.95

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'
S S 0.3331 0.5567 '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'

_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                   4.8832(3)
_cell_length_b                   7.6289(4)
_cell_length_c                   45.134(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.819(3)
_cell_angle_gamma                90
_cell_volume                     1681.21(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6864
_cell_measurement_theta_min      3.9181
_cell_measurement_theta_max      66.6191

_exptl_crystal_description       Acicular
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    1.636
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7898
_exptl_absorpt_correction_T_max  0.9492
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            11508
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         0.979
_diffrn_reflns_theta_max         66.614
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             2958
_reflns_number_gt                2868
_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 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1809P)²+5.4794P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2958
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0832
_refine_ls_wR_factor_ref         0.2736
_refine_ls_wR_factor_gt          0.2677
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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 0.1117(11) 0.0754(7) 0.57257(11) 0.0194(11) Uani 1 1 d . . . . .
H1 H -0.0007 -0.0208 0.5779 0.023 Uiso 1 1 calc R U . . .
C2 C 0.1066(10) 0.2326(7) 0.58611(11) 0.0189(11) Uani 1 1 d . . . . .
H2 H -0.0117 0.2597 0.6020 0.023 Uiso 1 1 calc R U . . .
C3 C 0.2977(10) 0.3545(6) 0.57407(10) 0.0156(10) Uani 1 1 d . . . . .
C4 C 0.4398(10) 0.2841(7) 0.55065(10) 0.0157(10) Uani 1 1 d . . . . .
C5 C 0.6408(10) 0.3800(6) 0.53447(10) 0.0149(10) Uani 1 1 d . . . . .
C6 C 0.7867(10) 0.3109(7) 0.51108(10) 0.0171(10) Uani 1 1 d . . . . .
H6 H 0.7554 0.1925 0.5054 0.021 Uiso 1 1 calc R U . . .
C7 C 0.9779(10) 0.4092(7) 0.49560(10) 0.0162(10) Uani 1 1 d . . . . .
C8 C 1.1271(10) 0.3413(6) 0.47194(10) 0.0154(10) Uani 1 1 d . . . . .
H8 H 1.0980 0.2229 0.4662 0.018 Uiso 1 1 calc R U . . .
C9 C 1.3165(10) 0.4413(6) 0.45659(11) 0.0161(10) Uani 1 1 d . . . . .
C10 C 0.5349(10) 0.6282(7) 0.56806(11) 0.0172(11) Uani 1 1 d . . . . .
H10 H 0.5684 0.7459 0.5740 0.021 Uiso 1 1 calc R U . . .
C11 C 0.3482(10) 0.5324(7) 0.58330(10) 0.0169(10) Uani 1 1 d . . . . .
C12 C 0.2044(11) 0.6046(7) 0.61001(10) 0.0187(11) Uani 1 1 d . . . . .
H12A H 0.0065 0.5775 0.6084 0.022 Uiso 1 1 calc R U . . .
H12B H 0.2249 0.7337 0.6104 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3192(11) 0.5279(7) 0.63898(11) 0.0196(11) Uani 1 1 d . . . . .
H13A H 0.2978 0.3989 0.6385 0.024 Uiso 1 1 calc R U . . .
H13B H 0.5176 0.5540 0.6404 0.024 Uiso 1 1 calc R U . . .
C14 C 0.1796(10) 0.5992(7) 0.66653(10) 0.0205(11) Uani 1 1 d . . . . .
H14A H 0.1989 0.7284 0.6670 0.025 Uiso 1 1 calc R U . . .
H14B H -0.0183 0.5714 0.6654 0.025 Uiso 1 1 calc R U . . .
C15 C 0.3007(11) 0.5226(8) 0.69508(11) 0.0224(12) Uani 1 1 d . . . . .
H15A H 0.2715 0.3942 0.6950 0.027 Uiso 1 1 calc R U . . .
H15B H 0.5008 0.5437 0.6954 0.027 Uiso 1 1 calc R U . . .
C16 C 0.1801(11) 0.5980(8) 0.72320(11) 0.0231(12) Uani 1 1 d . . . . .
H16A H -0.0198 0.5761 0.7231 0.028 Uiso 1 1 calc R U . . .
H16B H 0.2087 0.7264 0.7234 0.028 Uiso 1 1 calc R U . . .
C17 C 0.3063(11) 0.5196(8) 0.75122(11) 0.0236(12) Uani 1 1 d . . . . .
H17A H 0.5069 0.5379 0.7509 0.028 Uiso 1 1 calc R U . . .
H17B H 0.2728 0.3916 0.7512 0.028 Uiso 1 1 calc R U . . .
C18 C 0.1957(11) 0.5966(8) 0.77990(10) 0.0218(12) Uani 1 1 d . . . . .
H18A H 0.2299 0.7245 0.7801 0.026 Uiso 1 1 calc R U . . .
H18B H -0.0049 0.5782 0.7804 0.026 Uiso 1 1 calc R U . . .
C19 C 0.3265(11) 0.5145(8) 0.80739(11) 0.0231(12) Uani 1 1 d . . . . .
H19A H 0.2850 0.3875 0.8074 0.028 Uiso 1 1 calc R U . . .
H19B H 0.5277 0.5276 0.8062 0.028 Uiso 1 1 calc R U . . .
C20 C 0.2333(11) 0.5923(8) 0.83662(11) 0.0242(12) Uani 1 1 d . . . . .
H20A H 0.0323 0.5791 0.8381 0.029 Uiso 1 1 calc R U . . .
H20B H 0.2760 0.7192 0.8370 0.029 Uiso 1 1 calc R U . . .
C21 C 0.3727(12) 0.5032(8) 0.86334(11) 0.0274(13) Uani 1 1 d . . . . .
H21A H 0.3111 0.3812 0.8646 0.041 Uiso 1 1 calc R U . . .
H21B H 0.3242 0.5655 0.8815 0.041 Uiso 1 1 calc R U . . .
H21C H 0.5718 0.5061 0.8610 0.041 Uiso 1 1 calc R U . . .
S1 S 0.3464(2) 0.06879(16) 0.54429(3) 0.0184(4) 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 1.346(8) . ?
C1 S1 1.728(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.430(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(7) . ?
C3 C11 1.440(7) . ?
C4 C5 1.433(7) . ?
C4 S1 1.727(5) . ?
C5 C6 1.386(7) . ?
C5 C9 1.436(7) 3_766 ?
C6 C7 1.393(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(7) . ?
C7 C7 1.457(10) 3_766 ?
C8 C9 1.391(7) . ?
C8 H8 0.9500 . ?
C9 C5 1.436(7) 3_766 ?
C9 C10 1.438(7) 3_766 ?
C10 C11 1.362(8) . ?
C10 C9 1.438(7) 3_766 ?
C10 H10 0.9500 . ?
C11 C12 1.508(7) . ?
C12 C13 1.531(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.527(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.526(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.520(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.521(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.527(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.522(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.522(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.535(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C2 C1 S1 112.2(4) . . ?
C2 C1 H1 123.9 . . ?
S1 C1 H1 123.9 . . ?
C1 C2 C3 113.0(5) . . ?
C1 C2 H2 123.5 . . ?
C3 C2 H2 123.5 . . ?
C4 C3 C2 112.1(5) . . ?
C4 C3 C11 120.1(5) . . ?
C2 C3 C11 127.8(5) . . ?
C3 C4 C5 123.1(5) . . ?
C3 C4 S1 111.2(4) . . ?
C5 C4 S1 125.6(4) . . ?
C6 C5 C4 123.9(5) . . ?
C6 C5 C9 120.1(5) . 3_766 ?
C4 C5 C9 116.1(5) . 3_766 ?
C5 C6 C7 122.2(5) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C8 122.9(5) . . ?
C6 C7 C7 118.2(6) . 3_766 ?
C8 C7 C7 118.9(6) . 3_766 ?
C9 C8 C7 122.3(5) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C5 118.4(5) . 3_766 ?
C8 C9 C10 122.0(4) . 3_766 ?
C5 C9 C10 119.6(4) 3_766 3_766 ?
C11 C10 C9 122.8(5) . 3_766 ?
C11 C10 H10 118.6 . . ?
C9 C10 H10 118.6 3_766 . ?
C10 C11 C3 118.2(5) . . ?
C10 C11 C12 122.0(5) . . ?
C3 C11 C12 119.7(5) . . ?
C11 C12 C13 112.0(4) . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 113.4(4) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 112.3(4) . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 114.2(4) . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 112.9(5) . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 C18 114.2(5) . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 112.5(4) . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C18 114.8(4) . . ?
C20 C19 H19A 108.6 . . ?
C18 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C18 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 C21 111.9(4) . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20B 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 S1 C1 91.5(2) . . ?

_refine_diff_density_max         0.514
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.111

_shelxl_version_number           2014/6



