# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1413673'
_audit_update_record             
;
2015-07-20 deposited with the CCDC.
2016-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 Br O S2'
_chemical_formula_weight         339.26

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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   5.9198(2)
_cell_length_b                   8.4943(4)
_cell_length_c                   26.9054(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1352.93(10)
_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       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    3.330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3095
_exptl_absorpt_correction_T_max  0.5414
_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  'Bruker Smart Apex II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15751
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2386
_reflns_number_gt                2159
_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)+(0.0301P)²+0.2731P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2386
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0630
_refine_ls_wR_factor_gt          0.0608
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.12054(7) 0.35945(4) 0.052596(12) 0.06221(13) Uani 1 1 d . . .
S1 S -0.04820(16) 0.76356(10) -0.14175(3) 0.0561(2) Uani 1 1 d . . .
S2 S -0.36649(16) 0.49591(10) -0.16269(3) 0.0544(2) Uani 1 1 d . . .
O1 O 0.1490(4) 0.4029(3) -0.06135(7) 0.0578(6) Uani 1 1 d . . .
H1C H 0.2241 0.3608 -0.0395 0.087 Uiso 1 1 calc R . .
C1 C 0.0517(6) 0.7196(4) -0.20333(11) 0.0603(9) Uani 1 1 d . . .
H1A H 0.1126 0.8152 -0.2178 0.072 Uiso 1 1 calc R . .
H1B H 0.1745 0.6444 -0.2008 0.072 Uiso 1 1 calc R . .
C2 C -0.1243(5) 0.6539(3) -0.23812(10) 0.0442(6) Uani 1 1 d . . .
C3 C -0.1025(7) 0.6911(4) -0.28854(11) 0.0568(8) Uani 1 1 d . . .
H3A H 0.0198 0.7516 -0.2988 0.068 Uiso 1 1 calc R . .
C4 C -0.2558(7) 0.6411(5) -0.32324(12) 0.0634(9) Uani 1 1 d . . .
H4A H -0.2383 0.6693 -0.3564 0.076 Uiso 1 1 calc R . .
C5 C -0.4353(7) 0.5494(5) -0.30894(13) 0.0642(10) Uani 1 1 d . . .
H5A H -0.5403 0.5153 -0.3323 0.077 Uiso 1 1 calc R . .
C6 C -0.4585(6) 0.5082(4) -0.25935(12) 0.0577(9) Uani 1 1 d . . .
H6A H -0.5790 0.4451 -0.2496 0.069 Uiso 1 1 calc R . .
C7 C -0.3043(5) 0.5598(4) -0.22388(11) 0.0430(7) Uani 1 1 d . . .
C8 C -0.1272(6) 0.5640(3) -0.12667(9) 0.0417(6) Uani 1 1 d . . .
H8A H 0.0018 0.4952 -0.1337 0.050 Uiso 1 1 calc R . .
C9 C -0.1821(5) 0.5523(3) -0.07184(10) 0.0393(7) Uani 1 1 d . . .
C10 C -0.3750(5) 0.6221(3) -0.05227(11) 0.0468(6) Uani 1 1 d . . .
H10A H -0.4756 0.6733 -0.0733 0.056 Uiso 1 1 calc R . .
C11 C -0.4187(5) 0.6160(4) -0.00174(11) 0.0517(8) Uani 1 1 d . . .
H11A H -0.5478 0.6635 0.0110 0.062 Uiso 1 1 calc R . .
C12 C -0.2706(6) 0.5395(4) 0.02973(12) 0.0470(8) Uani 1 1 d . . .
H12A H -0.2987 0.5354 0.0637 0.056 Uiso 1 1 calc R . .
C13 C -0.0804(5) 0.4691(3) 0.01002(10) 0.0417(7) Uani 1 1 d . . .
C14 C -0.0340(5) 0.4738(3) -0.04078(10) 0.0393(7) 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
Br1 C13 1.896(3) . ?
S1 C1 1.798(3) . ?
S1 C8 1.804(3) . ?
S2 C7 1.772(3) . ?
S2 C8 1.811(3) . ?
O1 C14 1.357(3) . ?
O1 H1C 0.8200 . ?
C1 C2 1.508(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C7 1.386(4) . ?
C2 C3 1.399(4) . ?
C3 C4 1.369(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.373(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.386(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.391(4) . ?
C6 H6A 0.9300 . ?
C8 C9 1.514(4) . ?
C8 H8A 0.9800 . ?
C9 C14 1.382(4) . ?
C9 C10 1.390(4) . ?
C10 C11 1.385(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.381(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.381(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.395(4) . ?

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
C1 S1 C8 95.59(15) . . ?
C7 S2 C8 103.70(14) . . ?
C14 O1 H1C 109.5 . . ?
C2 C1 S1 114.9(2) . . ?
C2 C1 H1A 108.5 . . ?
S1 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
S1 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C7 C2 C3 118.0(3) . . ?
C7 C2 C1 125.0(2) . . ?
C3 C2 C1 117.0(3) . . ?
C4 C3 C2 122.0(4) . . ?
C4 C3 H3A 119.0 . . ?
C2 C3 H3A 119.0 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C5 C6 C7 121.1(3) . . ?
C5 C6 H6A 119.5 . . ?
C7 C6 H6A 119.5 . . ?
C2 C7 C6 119.8(3) . . ?
C2 C7 S2 126.4(2) . . ?
C6 C7 S2 113.9(3) . . ?
C9 C8 S1 109.7(2) . . ?
C9 C8 S2 109.4(2) . . ?
S1 C8 S2 112.49(16) . . ?
C9 C8 H8A 108.4 . . ?
S1 C8 H8A 108.4 . . ?
S2 C8 H8A 108.4 . . ?
C14 C9 C10 119.8(3) . . ?
C14 C9 C8 119.0(3) . . ?
C10 C9 C8 121.1(3) . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C12 C13 C14 121.7(3) . . ?
C12 C13 Br1 119.5(2) . . ?
C14 C13 Br1 118.8(2) . . ?
O1 C14 C9 118.3(2) . . ?
O1 C14 C13 123.0(3) . . ?
C9 C14 C13 118.8(3) . . ?

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
C8 S1 C1 C2 61.7(3) . . . . ?
S1 C1 C2 C7 -32.1(4) . . . . ?
S1 C1 C2 C3 148.0(3) . . . . ?
C7 C2 C3 C4 1.8(5) . . . . ?
C1 C2 C3 C4 -178.3(3) . . . . ?
C2 C3 C4 C5 -1.1(5) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C5 C6 C7 0.7(5) . . . . ?
C3 C2 C7 C6 -1.2(4) . . . . ?
C1 C2 C7 C6 178.9(3) . . . . ?
C3 C2 C7 S2 179.6(2) . . . . ?
C1 C2 C7 S2 -0.3(5) . . . . ?
C5 C6 C7 C2 0.0(5) . . . . ?
C5 C6 C7 S2 179.3(3) . . . . ?
C8 S2 C7 C2 -6.0(3) . . . . ?
C8 S2 C7 C6 174.8(2) . . . . ?
C1 S1 C8 C9 169.6(2) . . . . ?
C1 S1 C8 S2 -68.3(2) . . . . ?
C7 S2 C8 C9 166.6(2) . . . . ?
C7 S2 C8 S1 44.4(2) . . . . ?
S1 C8 C9 C14 -108.5(3) . . . . ?
S2 C8 C9 C14 127.7(2) . . . . ?
S1 C8 C9 C10 69.9(3) . . . . ?
S2 C8 C9 C10 -53.9(3) . . . . ?
C14 C9 C10 C11 1.0(4) . . . . ?
C8 C9 C10 C11 -177.3(3) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C11 C12 C13 Br1 -178.5(2) . . . . ?
C10 C9 C14 O1 178.0(3) . . . . ?
C8 C9 C14 O1 -3.6(4) . . . . ?
C10 C9 C14 C13 -1.2(4) . . . . ?
C8 C9 C14 C13 177.3(3) . . . . ?
C12 C13 C14 O1 -178.6(3) . . . . ?
Br1 C13 C14 O1 0.1(4) . . . . ?
C12 C13 C14 C9 0.6(4) . . . . ?
Br1 C13 C14 C9 179.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.520
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.046
