# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 983049'
_audit_update_record             
;
2014-01-23 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H26 Br2 S2'
_chemical_formula_weight         670.50

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'
Br Br -0.2901 2.4595 '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           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.2712(7)
_cell_length_b                   8.3649(3)
_cell_length_c                   14.4048(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.305(3)
_cell_angle_gamma                90.00
_cell_volume                     2919.69(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    2.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8962
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2871
_reflns_number_gt                2205
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0515P)²+2.7590P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2871
_refine_ls_number_parameters     181
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.046
_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
Br1 Br 0.152702(16) 0.43645(5) 0.55017(3) 0.04751(18) Uani 1 1 d . . .
S1 S 0.42413(4) 0.65950(12) 0.59522(7) 0.0369(3) Uani 1 1 d . . .
C11 C 0.22027(14) 0.5396(4) 0.5821(3) 0.0331(9) Uani 1 1 d . . .
C17 C 0.18730(18) 0.9738(5) 0.6317(3) 0.0412(10) Uani 1 1 d . . .
C10 C 0.27117(15) 0.4654(4) 0.5844(2) 0.0314(8) Uani 1 1 d . . .
C5 C 0.47389(15) 0.5254(5) 0.6359(3) 0.0375(9) Uani 1 1 d . . .
C16 C 0.23262(16) 1.0612(4) 0.6638(2) 0.0344(9) Uani 1 1 d . . .
H16 H 0.2259 1.1682 0.6765 0.041 Uiso 1 1 calc R . .
C6 C 0.53367(16) 0.5606(5) 0.6249(3) 0.0497(12) Uani 1 1 d . . .
H6A H 0.5377 0.6153 0.5671 0.075 Uiso 1 1 calc R . .
H6B H 0.5541 0.4623 0.6252 0.075 Uiso 1 1 calc R . .
H6C H 0.5476 0.6269 0.6754 0.075 Uiso 1 1 calc R . .
C7 C 0.37024(14) 0.5375(4) 0.6273(3) 0.0321(9) Uani 1 1 d . A .
C14 C 0.31086(15) 0.8640(4) 0.6627(2) 0.0314(8) Uani 1 1 d . . .
H14 H 0.3486 0.8568 0.6772 0.038 Uiso 1 1 calc R . .
C18 C 0.18358(15) 0.8135(5) 0.6074(2) 0.0362(9) Uani 1 1 d . . .
H18 H 0.1484 0.7764 0.5900 0.043 Uiso 1 1 calc R . .
C13 C 0.28602(14) 0.7260(4) 0.6270(2) 0.0276(8) Uani 1 1 d . . .
C3 C 0.47902(18) 0.2562(4) 0.7180(4) 0.0617(14) Uani 1 1 d D . .
C4 C 0.45044(16) 0.3935(5) 0.6725(3) 0.0431(11) Uani 1 1 d . A .
C15 C 0.28713(17) 1.0112(5) 0.6798(3) 0.0390(9) Uani 1 1 d . . .
H15 H 0.3111 1.0878 0.7058 0.047 Uiso 1 1 calc R . .
C9 C 0.31216(14) 0.5789(4) 0.6130(2) 0.0290(8) Uani 1 1 d . . .
C8 C 0.39156(15) 0.4016(4) 0.6656(3) 0.0397(10) Uani 1 1 d . . .
H8 H 0.3695 0.3193 0.6859 0.048 Uiso 1 1 calc R A .
C12 C 0.22527(14) 0.7027(4) 0.6058(2) 0.0283(8) Uani 1 1 d . . .
C2B C 0.4669(5) 0.0854(5) 0.6804(7) 0.0545(14) Uiso 0.584(15) 1 d PD A 2
H2BA H 0.4855 0.0638 0.6239 0.065 Uiso 0.584(15) 1 d PR A 2
H2BB H 0.4276 0.0658 0.6699 0.065 Uiso 0.584(15) 1 d PR A 2
C1A C 0.4922(3) -0.0110(9) 0.7644(6) 0.0545(14) Uiso 0.50 1 d PD . 1
H1AA H 0.4694 -0.0065 0.8175 0.065 Uiso 0.50 1 d PR . 1
H1AB H 0.5000 -0.1215 0.7500 0.065 Uiso 1 2 d SR . 1
C2A C 0.4537(3) 0.0861(6) 0.7193(13) 0.0545(14) Uiso 0.416(15) 1 d PD . 1
H2AA H 0.4342 0.0592 0.6607 0.065 Uiso 0.416(15) 1 d PR A 1
H2AB H 0.4292 0.0728 0.7698 0.065 Uiso 0.416(15) 1 d PR A 1
H17 H 0.155(2) 1.015(6) 0.627(3) 0.065 Uiso 1 1 d . . .
H10 H 0.2780(18) 0.353(6) 0.564(3) 0.065 Uiso 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
Br1 C11 1.886(3) . ?
S1 C5 1.726(4) . ?
S1 C7 1.742(4) . ?
C11 C10 1.381(5) . ?
C11 C12 1.410(5) . ?
C17 C16 1.378(6) . ?
C17 C18 1.388(6) . ?
C10 C9 1.419(5) . ?
C5 C4 1.361(6) . ?
C5 C6 1.498(5) . ?
C16 C15 1.394(5) . ?
C7 C8 1.353(5) . ?
C7 C9 1.455(5) . ?
C14 C13 1.387(5) . ?
C14 C15 1.388(5) . ?
C18 C12 1.373(5) . ?
C13 C9 1.404(5) . ?
C13 C12 1.501(4) . ?
C3 C3 1.333(8) 2_656 ?
C3 C4 1.476(5) . ?
C3 C2B 1.5500(10) . ?
C3 C2A 1.5501(10) . ?
C4 C8 1.428(5) . ?
C2B C1A 1.5514(10) . ?
C1A C2A 1.5505(10) 2_656 ?
C2A C1A 1.5506(10) 2_656 ?

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
C5 S1 C7 92.89(18) . . ?
C10 C11 C12 111.4(3) . . ?
C10 C11 Br1 124.3(3) . . ?
C12 C11 Br1 124.3(3) . . ?
C16 C17 C18 129.5(4) . . ?
C11 C10 C9 108.5(3) . . ?
C4 C5 C6 129.0(4) . . ?
C4 C5 S1 111.0(3) . . ?
C6 C5 S1 120.0(3) . . ?
C17 C16 C15 128.9(4) . . ?
C8 C7 C9 127.1(3) . . ?
C8 C7 S1 109.0(3) . . ?
C9 C7 S1 124.0(3) . . ?
C13 C14 C15 128.9(3) . . ?
C12 C18 C17 128.3(4) . . ?
C14 C13 C9 126.3(3) . . ?
C14 C13 C12 125.7(3) . . ?
C9 C13 C12 107.7(3) . . ?
C3 C3 C4 128.9(2) 2_656 . ?
C3 C3 C2B 111.3(3) 2_656 . ?
C4 C3 C2B 119.1(4) . . ?
C3 C3 C2A 106.2(5) 2_656 . ?
C4 C3 C2A 122.9(4) . . ?
C2B C3 C2A 24.6(5) . . ?
C5 C4 C8 111.9(3) . . ?
C5 C4 C3 127.3(4) . . ?
C8 C4 C3 120.7(4) . . ?
C14 C15 C16 129.5(4) . . ?
C13 C9 C10 108.2(3) . . ?
C13 C9 C7 129.1(3) . . ?
C10 C9 C7 122.6(3) . . ?
C7 C8 C4 115.2(4) . . ?
C18 C12 C11 127.1(3) . . ?
C18 C12 C13 128.7(3) . . ?
C11 C12 C13 104.2(3) . . ?
C3 C2B C1A 98.5(4) . . ?
C2A C1A C2B 98.0(6) 2_656 . ?
C3 C2A C1A 98.6(5) . 2_656 ?

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
C12 C11 C10 C9 1.7(4) . . . . ?
Br1 C11 C10 C9 -178.8(3) . . . . ?
C7 S1 C5 C4 -0.1(3) . . . . ?
C7 S1 C5 C6 177.8(3) . . . . ?
C18 C17 C16 C15 0.5(7) . . . . ?
C5 S1 C7 C8 -0.9(3) . . . . ?
C5 S1 C7 C9 179.8(3) . . . . ?
C16 C17 C18 C12 -3.0(7) . . . . ?
C15 C14 C13 C9 -178.6(4) . . . . ?
C15 C14 C13 C12 -5.4(6) . . . . ?
C6 C5 C4 C8 -176.6(4) . . . . ?
S1 C5 C4 C8 1.0(4) . . . . ?
C6 C5 C4 C3 5.5(7) . . . . ?
S1 C5 C4 C3 -176.9(4) . . . . ?
C3 C3 C4 C5 45.6(11) 2_656 . . . ?
C2B C3 C4 C5 -124.3(7) . . . . ?
C2A C3 C4 C5 -152.8(9) . . . . ?
C3 C3 C4 C8 -132.1(8) 2_656 . . . ?
C2B C3 C4 C8 57.9(8) . . . . ?
C2A C3 C4 C8 29.4(10) . . . . ?
C13 C14 C15 C16 -1.7(7) . . . . ?
C17 C16 C15 C14 4.3(7) . . . . ?
C14 C13 C9 C10 174.2(3) . . . . ?
C12 C13 C9 C10 0.0(4) . . . . ?
C14 C13 C9 C7 -3.3(6) . . . . ?
C12 C13 C9 C7 -177.5(3) . . . . ?
C11 C10 C9 C13 -1.0(4) . . . . ?
C11 C10 C9 C7 176.7(3) . . . . ?
C8 C7 C9 C13 138.4(4) . . . . ?
S1 C7 C9 C13 -42.4(5) . . . . ?
C8 C7 C9 C10 -38.8(6) . . . . ?
S1 C7 C9 C10 140.4(3) . . . . ?
C9 C7 C8 C4 -179.0(3) . . . . ?
S1 C7 C8 C4 1.7(4) . . . . ?
C5 C4 C8 C7 -1.8(5) . . . . ?
C3 C4 C8 C7 176.3(4) . . . . ?
C17 C18 C12 C11 179.0(4) . . . . ?
C17 C18 C12 C13 -2.1(6) . . . . ?
C10 C11 C12 C18 177.5(3) . . . . ?
Br1 C11 C12 C18 -2.0(5) . . . . ?
C10 C11 C12 C13 -1.6(4) . . . . ?
Br1 C11 C12 C13 178.9(2) . . . . ?
C14 C13 C12 C18 7.7(6) . . . . ?
C9 C13 C12 C18 -178.1(4) . . . . ?
C14 C13 C12 C11 -173.3(3) . . . . ?
C9 C13 C12 C11 1.0(4) . . . . ?
C3 C3 C2B C1A 23.4(10) 2_656 . . . ?
C4 C3 C2B C1A -164.9(6) . . . . ?
C2A C3 C2B C1A -59.0(11) . . . . ?
C3 C2B C1A C2A -44.5(7) . . . 2_656 ?
C3 C3 C2A C1A -37.6(12) 2_656 . . 2_656 ?
C4 C3 C2A C1A 157.3(7) . . . 2_656 ?
C2B C3 C2A C1A 68.3(11) . . . 2_656 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.079
