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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_tbr-brcpdb-c5br

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 Br2 S2'
_chemical_formula_sum            'C14 H12 Br2 S2'
_chemical_formula_weight         404.18

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   6.5657(4)
_cell_length_b                   15.4051(8)
_cell_length_c                   14.3212(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.183(5)
_cell_angle_gamma                90.00
_cell_volume                     1425.71(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1606
_cell_measurement_theta_min      3.0076
_cell_measurement_theta_max      28.5342

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    5.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.356
_exptl_absorpt_correction_T_max  0.551
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.2760
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5206
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_sigmaI/netI    0.1073
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2507
_reflns_number_gt                1578
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep
_computing_publication_material  Wingx

_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)+(0.0380P)²+0.0000P] 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         2507
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1381
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
Br18 Br 1.10861(13) 0.60969(6) 0.13199(6) 0.0526(3) Uani 1 1 d . . .
Br17 Br -0.00798(15) 0.37613(6) 0.44736(6) 0.0626(4) Uani 1 1 d . . .
S8 S 0.3288(3) 0.49363(14) 0.38718(13) 0.0462(6) Uani 1 1 d . . .
S5 S 0.7840(3) 0.58521(13) 0.26349(14) 0.0451(6) Uani 1 1 d . . .
C10 C 0.2305(12) 0.3496(5) 0.2984(5) 0.0376(19) Uani 1 1 d . . .
H10 H 0.1681 0.2965 0.2808 0.045 Uiso 1 1 calc R . .
C6 C 0.6167(11) 0.4997(4) 0.2512(5) 0.0305(17) Uani 1 1 d . . .
C12 C 0.3489(12) 0.3558(5) 0.0820(5) 0.041(2) Uani 1 1 d . . .
H12A H 0.2408 0.3154 0.0911 0.049 Uiso 1 1 calc R . .
H12B H 0.2845 0.4115 0.0648 0.049 Uiso 1 1 calc R . .
C14 C 0.5653(14) 0.2383(6) 0.0257(6) 0.061(3) Uani 1 1 d . . .
H14A H 0.6340 0.2213 -0.0261 0.073 Uiso 1 1 calc R . .
H14B H 0.4672 0.1931 0.0342 0.073 Uiso 1 1 calc R . .
C7 C 0.4575(11) 0.4651(5) 0.2979(5) 0.0336(18) Uani 1 1 d . . .
C2 C 0.6479(11) 0.4435(5) 0.1789(5) 0.0354(18) Uani 1 1 d . . .
C1 C 0.5028(11) 0.3654(5) 0.1764(5) 0.0335(18) Uani 1 1 d . . .
C9 C 0.1830(12) 0.4019(5) 0.3687(5) 0.040(2) Uani 1 1 d . . .
C3 C 0.8090(11) 0.4701(5) 0.1319(5) 0.0346(18) Uani 1 1 d . . .
H3 H 0.8507 0.4407 0.0818 0.042 Uiso 1 1 calc R . .
C16 C 0.6244(12) 0.2797(5) 0.1969(5) 0.046(2) Uani 1 1 d . . .
H16A H 0.7300 0.2877 0.2528 0.055 Uiso 1 1 calc R . .
H16B H 0.5304 0.2352 0.2114 0.055 Uiso 1 1 calc R . .
C11 C 0.3882(12) 0.3878(5) 0.2560(5) 0.0345(19) Uani 1 1 d . . .
C15 C 0.7261(12) 0.2482(5) 0.1171(5) 0.048(2) Uani 1 1 d . . .
H15A H 0.7923 0.1927 0.1340 0.057 Uiso 1 1 calc R . .
H15B H 0.8320 0.2891 0.1065 0.057 Uiso 1 1 calc R . .
C13 C 0.4504(12) 0.3238(5) 0.0014(5) 0.049(2) Uani 1 1 d . . .
H13A H 0.5471 0.3673 -0.0130 0.058 Uiso 1 1 calc R . .
H13B H 0.3454 0.3158 -0.0548 0.058 Uiso 1 1 calc R . .
C4 C 0.8956(11) 0.5464(5) 0.1714(4) 0.0352(18) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br18 0.0472(6) 0.0585(6) 0.0547(6) 0.0053(4) 0.0159(4) -0.0142(4)
Br17 0.0651(7) 0.0759(7) 0.0560(6) 0.0019(5) 0.0361(5) -0.0061(5)
S8 0.0524(14) 0.0522(14) 0.0378(11) -0.0035(11) 0.0181(11) 0.0000(11)
S5 0.0496(14) 0.0407(12) 0.0475(12) -0.0020(10) 0.0155(10) -0.0047(11)
C10 0.040(5) 0.038(4) 0.034(4) 0.001(4) 0.007(4) 0.000(4)
C6 0.031(4) 0.027(4) 0.033(4) 0.000(4) 0.006(3) 0.003(3)
C12 0.039(5) 0.046(5) 0.040(4) -0.007(4) 0.012(4) 0.003(4)
C14 0.061(7) 0.063(6) 0.061(6) -0.026(5) 0.015(5) 0.006(5)
C7 0.039(5) 0.033(4) 0.030(4) 0.001(4) 0.009(4) 0.004(4)
C2 0.034(5) 0.034(4) 0.038(4) -0.010(4) 0.004(4) -0.008(4)
C1 0.028(4) 0.032(4) 0.041(4) 0.007(4) 0.010(4) 0.008(3)
C9 0.042(5) 0.050(5) 0.030(4) 0.000(4) 0.013(4) -0.004(4)
C3 0.042(5) 0.036(4) 0.028(4) 0.002(4) 0.014(4) 0.000(4)
C16 0.041(5) 0.041(5) 0.055(5) -0.008(4) 0.008(4) 0.001(4)
C11 0.039(5) 0.036(5) 0.030(4) 0.019(4) 0.008(4) 0.017(4)
C15 0.040(5) 0.041(5) 0.060(5) -0.003(5) 0.003(4) 0.009(4)
C13 0.034(5) 0.069(6) 0.040(5) -0.003(4) -0.001(4) 0.009(4)
C4 0.036(5) 0.034(4) 0.033(4) 0.019(4) 0.001(4) 0.003(4)

_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
Br18 C4 1.872(7) . ?
Br17 C9 1.870(7) . ?
S8 C9 1.701(8) . ?
S8 C7 1.711(7) . ?
S5 C6 1.705(7) . ?
S5 C4 1.725(7) . ?
C10 C9 1.368(10) . ?
C10 C11 1.417(10) . ?
C6 C2 1.392(9) . ?
C6 C7 1.439(9) . ?
C12 C13 1.514(9) . ?
C12 C1 1.545(9) . ?
C14 C13 1.527(10) . ?
C14 C15 1.537(10) . ?
C7 C11 1.374(10) . ?
C2 C3 1.412(9) . ?
C2 C1 1.531(10) . ?
C1 C11 1.512(9) . ?
C1 C16 1.543(10) . ?
C3 C4 1.382(10) . ?
C16 C15 1.503(9) . ?

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
C9 S8 C7 90.5(4) . . ?
C6 S5 C4 90.3(3) . . ?
C9 C10 C11 110.5(7) . . ?
C2 C6 C7 109.2(6) . . ?
C2 C6 S5 112.4(5) . . ?
C7 C6 S5 138.2(5) . . ?
C13 C12 C1 113.0(6) . . ?
C13 C14 C15 110.3(7) . . ?
C11 C7 C6 109.2(6) . . ?
C11 C7 S8 112.3(6) . . ?
C6 C7 S8 138.4(6) . . ?
C6 C2 C3 113.3(6) . . ?
C6 C2 C1 109.5(6) . . ?
C3 C2 C1 137.1(6) . . ?
C11 C1 C2 101.2(6) . . ?
C11 C1 C16 111.2(6) . . ?
C2 C1 C16 111.6(6) . . ?
C11 C1 C12 110.2(6) . . ?
C2 C1 C12 113.8(6) . . ?
C16 C1 C12 108.7(6) . . ?
C10 C9 S8 114.1(6) . . ?
C10 C9 Br17 125.7(6) . . ?
S8 C9 Br17 120.1(4) . . ?
C4 C3 C2 109.9(6) . . ?
C15 C16 C1 114.6(6) . . ?
C7 C11 C10 112.5(7) . . ?
C7 C11 C1 110.9(6) . . ?
C10 C11 C1 136.6(7) . . ?
C16 C15 C14 110.4(6) . . ?
C12 C13 C14 111.8(7) . . ?
C3 C4 S5 114.1(5) . . ?
C3 C4 Br18 126.5(6) . . ?
S5 C4 Br18 119.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.132
_database_code_depnum_ccdc_archive 'CCDC 1005162'
