# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# 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_a
_audit_block_doi                 10.5517/cc13l0tj
_database_code_depnum_ccdc_archive 'CCDC 1030217'
_audit_update_record             
;
2014-10-21 deposited with the CCDC.
2014-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H32 N2 S2'
_chemical_formula_weight         532.74

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.615(6)
_cell_length_b                   9.543(7)
_cell_length_c                   10.259(8)
_cell_angle_alpha                83.045(12)
_cell_angle_beta                 77.140(11)
_cell_angle_gamma                81.412(12)
_cell_volume                     715.6(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1218
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      24.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             282
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9609
_exptl_absorpt_correction_T_max  0.9751
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            3641
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2493
_reflns_number_gt                1936
_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)+(0.0693P)²+0.0281P] 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         2493
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1279
_refine_ls_wR_factor_gt          0.1192
_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 0.15288(8) 0.90328(6) 0.75709(6) 0.0425(2) Uani 1 1 d . . .
N1 N -0.0843(2) 0.78621(18) 0.35440(18) 0.0359(4) Uani 1 1 d . . .
C11 C 0.0272(3) 0.8565(2) 0.5494(2) 0.0346(5) Uani 1 1 d . . .
C10 C 0.0664(3) 0.7187(2) 0.6199(2) 0.0369(5) Uani 1 1 d . . .
H10 H 0.0491 0.6332 0.5925 0.044 Uiso 1 1 calc R . .
C13 C -0.0430(3) 0.8891(2) 0.4311(2) 0.0330(5) Uani 1 1 d . . .
C6 C 0.2697(3) 0.3849(2) 0.9789(2) 0.0383(5) Uani 1 1 d . . .
C8 C 0.1823(3) 0.6113(2) 0.8228(2) 0.0410(6) Uani 1 1 d . . .
C12 C 0.0680(3) 0.9672(2) 0.6145(2) 0.0338(5) Uani 1 1 d . . .
C1 C 0.2492(3) 0.2502(3) 0.9491(2) 0.0478(6) Uani 1 1 d . . .
H1 H 0.2018 0.2409 0.8749 0.057 Uiso 1 1 calc R . .
C9 C 0.1323(3) 0.7290(2) 0.7321(2) 0.0377(5) Uani 1 1 d . . .
C7 C 0.2208(3) 0.5096(2) 0.8944(2) 0.0430(6) Uani 1 1 d . . .
C14 C -0.2362(3) 0.7080(2) 0.4244(2) 0.0446(6) Uani 1 1 d . . .
H14A H -0.2097 0.6604 0.5082 0.054 Uiso 1 1 calc R . .
H14B H -0.2489 0.6358 0.3694 0.054 Uiso 1 1 calc R . .
C5 C 0.3400(3) 0.3963(3) 1.0904(2) 0.0454(6) Uani 1 1 d . . .
H5 H 0.3537 0.4855 1.1118 0.054 Uiso 1 1 calc R . .
C3 C 0.3684(3) 0.1446(3) 1.1398(3) 0.0577(7) Uani 1 1 d . . .
H3 H 0.4008 0.0639 1.1942 0.069 Uiso 1 1 calc R . .
C2 C 0.2990(3) 0.1310(3) 1.0291(3) 0.0568(7) Uani 1 1 d . . .
H2 H 0.2858 0.0413 1.0086 0.068 Uiso 1 1 calc R . .
C4 C 0.3898(3) 0.2754(3) 1.1697(2) 0.0523(7) Uani 1 1 d . . .
H4 H 0.4381 0.2835 1.2438 0.063 Uiso 1 1 calc R . .
C16 C 0.0773(3) 0.6919(2) 0.2937(2) 0.0482(6) Uani 1 1 d . . .
H16A H 0.0407 0.6238 0.2453 0.058 Uiso 1 1 calc R . .
H16B H 0.1334 0.6394 0.3641 0.058 Uiso 1 1 calc R . .
C15 C -0.4113(3) 0.8057(3) 0.4530(3) 0.0658(8) Uani 1 1 d . . .
H15A H -0.4025 0.8723 0.5136 0.099 Uiso 1 1 calc R . .
H15B H -0.5088 0.7508 0.4931 0.099 Uiso 1 1 calc R . .
H15C H -0.4347 0.8564 0.3707 0.099 Uiso 1 1 calc R . .
C17 C 0.2139(4) 0.7759(3) 0.1985(4) 0.0876(11) Uani 1 1 d . . .
H17A H 0.1589 0.8274 0.1284 0.131 Uiso 1 1 calc R . .
H17B H 0.3169 0.7119 0.1600 0.131 Uiso 1 1 calc R . .
H17C H 0.2526 0.8417 0.2467 0.131 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 C12 1.737(2) . ?
S1 C9 1.748(3) . ?
N1 C13 1.440(3) . ?
N1 C14 1.473(3) . ?
N1 C16 1.475(3) . ?
C11 C13 1.415(3) . ?
C11 C12 1.421(3) . ?
C11 C10 1.446(3) . ?
C10 C9 1.373(3) . ?
C10 H10 0.9300 . ?
C13 C12 1.393(3) 2_576 ?
C6 C1 1.395(3) . ?
C6 C5 1.388(3) . ?
C6 C7 1.438(3) . ?
C8 C7 1.186(3) . ?
C8 C9 1.431(3) . ?
C12 C13 1.393(3) 2_576 ?
C1 C2 1.376(3) . ?
C1 H1 0.9300 . ?
C14 C15 1.502(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C5 C4 1.385(3) . ?
C5 H5 0.9300 . ?
C3 C4 1.362(4) . ?
C3 C2 1.382(4) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
C16 C17 1.511(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C12 S1 C9 90.53(10) . . ?
C13 N1 C14 114.37(18) . . ?
C13 N1 C16 113.21(17) . . ?
C14 N1 C16 112.89(18) . . ?
C13 C11 C12 120.18(18) . . ?
C13 C11 C10 128.5(2) . . ?
C12 C11 C10 111.30(19) . . ?
C9 C10 C11 111.9(2) . . ?
C9 C10 H10 124.0 . . ?
C11 C10 H10 124.0 . . ?
C12 C13 C11 116.08(19) 2_576 . ?
C12 C13 N1 118.71(19) 2_576 . ?
C11 C13 N1 125.19(18) . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 C7 120.5(2) . . ?
C5 C6 C7 120.6(2) . . ?
C7 C8 C9 176.8(3) . . ?
C13 C12 C11 123.74(19) 2_576 . ?
C13 C12 S1 123.81(17) 2_576 . ?
C11 C12 S1 112.45(15) . . ?
C6 C1 C2 120.2(2) . . ?
C6 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C10 C9 C8 125.1(2) . . ?
C10 C9 S1 113.78(15) . . ?
C8 C9 S1 121.15(18) . . ?
C8 C7 C6 178.8(3) . . ?
N1 C14 C15 111.5(2) . . ?
N1 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
N1 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C16 C17 111.3(2) . . ?
N1 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N1 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C13 C11 C10 C9 -179.53(19) . . . . ?
C12 C11 C10 C9 0.3(3) . . . . ?
C12 C11 C13 C12 -0.1(3) . . . 2_576 ?
C10 C11 C13 C12 179.73(19) . . . 2_576 ?
C12 C11 C13 N1 178.06(19) . . . . ?
C10 C11 C13 N1 -2.2(3) . . . . ?
C14 N1 C13 C12 -115.1(2) . . . 2_576 ?
C16 N1 C13 C12 113.7(2) . . . 2_576 ?
C14 N1 C13 C11 66.8(3) . . . . ?
C16 N1 C13 C11 -64.4(3) . . . . ?
C13 C11 C12 C13 0.1(4) . . . 2_576 ?
C10 C11 C12 C13 -179.76(18) . . . 2_576 ?
C13 C11 C12 S1 -179.87(15) . . . . ?
C10 C11 C12 S1 0.3(2) . . . . ?
C9 S1 C12 C13 179.47(19) . . . 2_576 ?
C9 S1 C12 C11 -0.60(17) . . . . ?
C5 C6 C1 C2 -0.3(4) . . . . ?
C7 C6 C1 C2 179.0(2) . . . . ?
C11 C10 C9 C8 179.58(19) . . . . ?
C11 C10 C9 S1 -0.7(2) . . . . ?
C7 C8 C9 C10 -4(5) . . . . ?
C7 C8 C9 S1 176(4) . . . . ?
C12 S1 C9 C10 0.77(17) . . . . ?
C12 S1 C9 C8 -179.53(18) . . . . ?
C9 C8 C7 C6 56(14) . . . . ?
C1 C6 C7 C8 -52(12) . . . . ?
C5 C6 C7 C8 127(12) . . . . ?
C13 N1 C14 C15 63.6(2) . . . . ?
C16 N1 C14 C15 -165.0(2) . . . . ?
C1 C6 C5 C4 0.5(3) . . . . ?
C7 C6 C5 C4 -178.8(2) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
C4 C3 C2 C1 -0.6(4) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C6 C5 C4 C3 -0.7(4) . . . . ?
C13 N1 C16 C17 -60.4(3) . . . . ?
C14 N1 C16 C17 167.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.042
