# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_sa3394
_database_code_depnum_ccdc_archive 'CCDC 1400329'
_audit_update_record             
;
2015-05-12 deposited with the CCDC.
2016-09-09 downloaded from the CCDC.
;
_audit_creation_date             2014-05-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H4 Br2 O2 S2'
_chemical_formula_sum            'C10 H4 Br2 O2 S2'
_chemical_formula_weight         380.07
_chemical_absolute_configuration ?
_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 0.0033 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'
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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   5.7908(6)
_cell_length_b                   11.3325(13)
_cell_length_c                   17.3880(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1141.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4291
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4822
_cell_measurement_theta_min      2.1451
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.448
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4648
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.596
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             1546
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0303
_diffrn_orient_matrix_UB_12      -0.1626
_diffrn_orient_matrix_UB_13      0.0495
_diffrn_orient_matrix_UB_21      0.0831
_diffrn_orient_matrix_UB_22      -0.0067
_diffrn_orient_matrix_UB_23      0.0290
_diffrn_orient_matrix_UB_31      -0.0165
_diffrn_orient_matrix_UB_32      0.0189
_diffrn_orient_matrix_UB_33      0.0518
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                2449
_reflns_number_total             2548
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details 
;
 Flack x determined using 927 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.023(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2548
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0188P)²+0.7520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0571
_refine_ls_wR_factor_ref         0.0582
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Br1 Br 0.67021(9) 0.02452(4) 0.81236(3) 0.02711(13) Uani 1 1 d . . . . .
Br2 Br 1.28148(10) 0.72074(5) 0.34055(3) 0.03341(15) Uani 1 1 d . . . . .
S1 S 0.7627(2) 0.22072(10) 0.69184(6) 0.0216(2) Uani 1 1 d . . . . .
S2 S 1.1943(2) 0.51160(10) 0.45312(7) 0.0226(3) Uani 1 1 d . . . . .
O1 O 1.2303(6) 0.3011(3) 0.53411(19) 0.0264(8) Uani 1 1 d . . . . .
O2 O 0.7131(6) 0.4136(3) 0.60140(19) 0.0304(8) Uani 1 1 d . . . . .
C1 C 0.8586(9) 0.0961(4) 0.7379(2) 0.0232(10) Uani 1 1 d . . . . .
C2 C 1.0678(9) 0.0573(4) 0.7127(3) 0.0236(10) Uani 1 1 d . . . . .
H2 H 1.1435 -0.0090 0.7316 0.028 Uiso 1 1 calc R . . . .
C3 C 1.1540(8) 0.1307(4) 0.6545(3) 0.0227(10) Uani 1 1 d . . . . .
H3 H 1.2959 0.1183 0.6308 0.027 Uiso 1 1 calc R . . . .
C4 C 1.0114(8) 0.2219(4) 0.6357(2) 0.0192(9) Uani 1 1 d . . . . .
C5 C 1.0600(9) 0.3080(4) 0.5750(3) 0.0220(10) Uani 1 1 d . . . . .
C6 C 0.8891(8) 0.4110(4) 0.5633(3) 0.0212(10) Uani 1 1 d . . . . .
C7 C 0.9440(8) 0.5021(4) 0.5066(2) 0.0192(10) Uani 1 1 d . . . . .
C8 C 0.7984(9) 0.5940(4) 0.4911(3) 0.0250(10) Uani 1 1 d . . . . .
H8 H 0.6554 0.6030 0.5147 0.030 Uiso 1 1 calc R . . . .
C9 C 0.8843(9) 0.6732(5) 0.4365(3) 0.0267(11) Uani 1 1 d . . . . .
H9 H 0.8066 0.7401 0.4195 0.032 Uiso 1 1 calc R . . . .
C10 C 1.0973(9) 0.6392(4) 0.4115(3) 0.0251(11) 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 C1 1.877(5) . ?
Br2 C10 1.874(5) . ?
S1 C1 1.716(5) . ?
S1 C4 1.740(4) . ?
S2 C7 1.725(5) . ?
S2 C10 1.712(5) . ?
O1 C5 1.218(6) . ?
O2 C6 1.216(5) . ?
C1 C2 1.361(7) . ?
C2 C3 1.402(7) . ?
C3 C4 1.363(7) . ?
C4 C5 1.465(6) . ?
C5 C6 1.543(7) . ?
C6 C7 1.463(6) . ?
C7 C8 1.367(6) . ?
C8 C9 1.398(7) . ?
C9 C10 1.363(7) . ?

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 C4 90.0(2) . . ?
C10 S2 C7 90.3(2) . . ?
S1 C1 Br1 119.3(3) . . ?
C2 C1 Br1 126.9(4) . . ?
C2 C1 S1 113.8(4) . . ?
C1 C2 C3 111.0(5) . . ?
C4 C3 C2 114.1(5) . . ?
C3 C4 S1 111.1(4) . . ?
C3 C4 C5 124.2(4) . . ?
C5 C4 S1 124.7(4) . . ?
O1 C5 C4 122.2(5) . . ?
O1 C5 C6 119.4(4) . . ?
C4 C5 C6 118.4(4) . . ?
O2 C6 C5 119.0(4) . . ?
O2 C6 C7 122.2(4) . . ?
C7 C6 C5 118.9(4) . . ?
C6 C7 S2 126.1(4) . . ?
C8 C7 S2 111.4(4) . . ?
C8 C7 C6 122.5(4) . . ?
C7 C8 C9 113.8(5) . . ?
C10 C9 C8 110.9(5) . . ?
S2 C10 Br2 120.5(3) . . ?
C9 C10 Br2 125.8(4) . . ?
C9 C10 S2 113.6(4) . . ?

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
Br1 C1 C2 C3 177.6(3) . . . . ?
S1 C1 C2 C3 0.2(5) . . . . ?
S1 C4 C5 O1 -175.6(4) . . . . ?
S1 C4 C5 C6 4.8(6) . . . . ?
S2 C7 C8 C9 0.0(5) . . . . ?
O1 C5 C6 O2 176.0(4) . . . . ?
O1 C5 C6 C7 -3.9(6) . . . . ?
O2 C6 C7 S2 176.3(4) . . . . ?
O2 C6 C7 C8 -2.0(7) . . . . ?
C1 S1 C4 C3 -0.7(4) . . . . ?
C1 S1 C4 C5 178.2(4) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C2 C3 C4 S1 0.9(5) . . . . ?
C2 C3 C4 C5 -177.9(4) . . . . ?
C3 C4 C5 O1 3.1(7) . . . . ?
C3 C4 C5 C6 -176.5(4) . . . . ?
C4 S1 C1 Br1 -177.4(3) . . . . ?
C4 S1 C1 C2 0.3(4) . . . . ?
C4 C5 C6 O2 -4.4(6) . . . . ?
C4 C5 C6 C7 175.7(4) . . . . ?
C5 C6 C7 S2 -3.7(6) . . . . ?
C5 C6 C7 C8 177.9(4) . . . . ?
C6 C7 C8 C9 178.6(4) . . . . ?
C7 S2 C10 Br2 178.3(3) . . . . ?
C7 S2 C10 C9 -0.3(4) . . . . ?
C7 C8 C9 C10 -0.2(6) . . . . ?
C8 C9 C10 Br2 -178.2(4) . . . . ?
C8 C9 C10 S2 0.3(6) . . . . ?
C10 S2 C7 C6 -178.4(4) . . . . ?
C10 S2 C7 C8 0.2(4) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DICHLOROMETHANE/METHANOL'
