# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_compound3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 Br3 S2'
_chemical_formula_weight         511.13

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.932(6)
_cell_length_b                   10.674(8)
_cell_length_c                   10.901(9)
_cell_angle_alpha                91.188(12)
_cell_angle_beta                 106.211(11)
_cell_angle_gamma                90.163(12)
_cell_volume                     886.0(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2
_cell_measurement_theta_max      30

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    7.056
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4775
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'software bruker'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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 APEX II '
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14050
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_sigmaI/netI    0.0769
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         30.77
_reflns_number_total             5475
_reflns_number_gt                2755
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'APEX II (Bruker, 2008)'
_computing_cell_refinement       'APEX II (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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)+(0.0449P)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         5475
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_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
C1 C 0.4205(5) 0.4596(4) 0.6680(4) 0.0406(9) Uani 1 1 d . . .
C2 C 0.3222(5) 0.5463(4) 0.5952(4) 0.0406(9) Uani 1 1 d . . .
H2 H 0.3179 0.6297 0.6204 0.049 Uiso 1 1 calc R . .
C3 C 0.2248(5) 0.4957(3) 0.4744(3) 0.0342(8) Uani 1 1 d . . .
C4 C 0.1066(5) 0.5533(4) 0.3680(4) 0.0361(9) Uani 1 1 d . . .
C5 C 0.0541(5) 0.6814(4) 0.3462(4) 0.0393(9) Uani 1 1 d . . .
C6 C -0.0574(6) 0.6960(4) 0.2287(4) 0.0450(10) Uani 1 1 d . . .
C7 C 0.0293(5) 0.4761(4) 0.2615(3) 0.0370(9) Uani 1 1 d . . .
C8 C 0.0574(5) 0.3478(4) 0.2516(4) 0.0403(9) Uani 1 1 d . . .
C9 C 0.1744(5) 0.2914(4) 0.3543(4) 0.0399(9) Uani 1 1 d . . .
C10 C 0.2539(5) 0.3676(3) 0.4618(4) 0.0365(9) Uani 1 1 d . . .
C11 C -0.0412(6) 0.2747(4) 0.1330(4) 0.0502(11) Uani 1 1 d . . .
H11A H 0.0306 0.2052 0.1194 0.060 Uiso 1 1 calc R . .
H11B H -0.0605 0.3286 0.0599 0.060 Uiso 1 1 calc R . .
C12 C -0.2172(6) 0.2239(5) 0.1407(4) 0.0616(13) Uani 1 1 d . . .
H12A H -0.2892 0.2932 0.1543 0.074 Uiso 1 1 calc R . .
H12B H -0.1981 0.1697 0.2135 0.074 Uiso 1 1 calc R . .
C13 C -0.3148(8) 0.1510(5) 0.0209(5) 0.0874(19) Uani 1 1 d . . .
H13A H -0.3406 0.2055 -0.0508 0.131 Uiso 1 1 calc R . .
H13B H -0.4224 0.1180 0.0316 0.131 Uiso 1 1 calc R . .
H13C H -0.2432 0.0832 0.0059 0.131 Uiso 1 1 calc R . .
C14 C 0.2240(6) 0.1554(4) 0.3502(4) 0.0486(11) Uani 1 1 d . . .
H14A H 0.1243 0.1078 0.2981 0.058 Uiso 1 1 calc R . .
H14B H 0.2533 0.1228 0.4360 0.058 Uiso 1 1 calc R . .
C15 C 0.3806(7) 0.1380(4) 0.2954(5) 0.0641(13) Uani 1 1 d . . .
H15A H 0.3476 0.1649 0.2075 0.077 Uiso 1 1 calc R . .
H15B H 0.4767 0.1914 0.3433 0.077 Uiso 1 1 calc R . .
C16 C 0.4432(8) 0.0049(5) 0.2993(5) 0.0825(18) Uani 1 1 d . . .
H16A H 0.4690 -0.0242 0.3853 0.124 Uiso 1 1 calc R . .
H16B H 0.5473 0.0011 0.2709 0.124 Uiso 1 1 calc R . .
H16C H 0.3533 -0.0471 0.2443 0.124 Uiso 1 1 calc R . .
Br1 Br 0.57096(6) 0.48575(5) 0.83404(4) 0.05871(16) Uani 1 1 d . . .
Br2 Br -0.15636(8) 0.84614(5) 0.15959(5) 0.07314(19) Uani 1 1 d . . .
Br3 Br 0.12449(7) 0.81430(4) 0.46398(5) 0.05619(15) Uani 1 1 d . . .
S1 S 0.40295(15) 0.31242(10) 0.59953(10) 0.0464(3) Uani 1 1 d . . .
S2 S -0.10456(15) 0.56156(11) 0.13836(10) 0.0489(3) 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
C1 0.035(2) 0.047(2) 0.037(2) -0.0035(18) 0.0062(18) 0.0007(19)
C2 0.043(2) 0.040(2) 0.039(2) -0.0023(18) 0.0120(18) -0.0022(19)
C3 0.032(2) 0.038(2) 0.036(2) 0.0031(16) 0.0143(17) 0.0025(17)
C4 0.033(2) 0.039(2) 0.039(2) 0.0032(17) 0.0140(17) -0.0007(17)
C5 0.038(2) 0.040(2) 0.041(2) 0.0067(18) 0.0132(18) 0.0048(18)
C6 0.048(3) 0.044(2) 0.046(2) 0.0102(19) 0.016(2) 0.013(2)
C7 0.035(2) 0.044(2) 0.034(2) 0.0050(17) 0.0115(17) -0.0012(18)
C8 0.044(2) 0.044(2) 0.036(2) -0.0020(18) 0.0178(18) -0.0046(19)
C9 0.045(2) 0.036(2) 0.043(2) 0.0006(18) 0.0176(19) -0.0036(19)
C10 0.036(2) 0.036(2) 0.039(2) 0.0074(17) 0.0116(17) 0.0006(17)
C11 0.062(3) 0.043(2) 0.043(2) -0.0020(19) 0.011(2) 0.001(2)
C12 0.057(3) 0.060(3) 0.060(3) -0.006(2) 0.004(2) -0.009(3)
C13 0.101(5) 0.067(4) 0.068(4) -0.006(3) -0.019(3) -0.024(3)
C14 0.053(3) 0.041(2) 0.051(3) -0.0010(19) 0.012(2) -0.001(2)
C15 0.065(3) 0.049(3) 0.081(4) -0.002(3) 0.025(3) 0.009(3)
C16 0.109(5) 0.067(4) 0.077(4) -0.007(3) 0.036(4) 0.027(3)
Br1 0.0486(3) 0.0776(4) 0.0421(3) 0.0049(2) -0.0006(2) -0.0008(2)
Br2 0.0848(4) 0.0637(3) 0.0679(3) 0.0218(3) 0.0145(3) 0.0297(3)
Br3 0.0671(3) 0.0402(2) 0.0598(3) -0.0014(2) 0.0154(2) 0.0021(2)
S1 0.0465(6) 0.0433(6) 0.0467(6) 0.0097(5) 0.0081(5) 0.0058(5)
S2 0.0494(7) 0.0568(7) 0.0375(6) 0.0059(5) 0.0066(5) 0.0059(6)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.335(5) . ?
C1 S1 1.714(4) . ?
C1 Br1 1.884(4) . ?
C2 C3 1.423(5) . ?
C2 H2 0.9300 . ?
C3 C10 1.398(5) . ?
C3 C4 1.423(5) . ?
C4 C7 1.401(5) . ?
C4 C5 1.436(5) . ?
C5 C6 1.350(5) . ?
C5 Br3 1.869(4) . ?
C6 S2 1.704(5) . ?
C6 Br2 1.865(4) . ?
C7 C8 1.396(6) . ?
C7 S2 1.738(4) . ?
C8 C9 1.389(5) . ?
C8 C11 1.510(6) . ?
C9 C10 1.406(5) . ?
C9 C14 1.508(6) . ?
C10 S1 1.746(4) . ?
C11 C12 1.521(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.517(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.532(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.504(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C2 C1 S1 114.8(3) . . ?
C2 C1 Br1 126.2(3) . . ?
S1 C1 Br1 119.0(2) . . ?
C1 C2 C3 111.9(4) . . ?
C1 C2 H2 124.0 . . ?
C3 C2 H2 124.0 . . ?
C10 C3 C4 116.7(4) . . ?
C10 C3 C2 112.3(3) . . ?
C4 C3 C2 131.0(4) . . ?
C7 C4 C3 117.0(3) . . ?
C7 C4 C5 111.6(3) . . ?
C3 C4 C5 131.3(4) . . ?
C6 C5 C4 111.8(4) . . ?
C6 C5 Br3 122.7(3) . . ?
C4 C5 Br3 125.5(3) . . ?
C5 C6 S2 114.5(3) . . ?
C5 C6 Br2 126.3(3) . . ?
S2 C6 Br2 119.2(2) . . ?
C8 C7 C4 125.4(4) . . ?
C8 C7 S2 123.3(3) . . ?
C4 C7 S2 111.3(3) . . ?
C9 C8 C7 117.8(4) . . ?
C9 C8 C11 122.3(4) . . ?
C7 C8 C11 119.9(4) . . ?
C8 C9 C10 117.5(4) . . ?
C8 C9 C14 122.2(4) . . ?
C10 C9 C14 120.2(4) . . ?
C3 C10 C9 125.5(4) . . ?
C3 C10 S1 110.8(3) . . ?
C9 C10 S1 123.7(3) . . ?
C8 C11 C12 113.1(4) . . ?
C8 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C8 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 112.6(4) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 C15 111.7(4) . . ?
C9 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C9 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 113.3(4) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 S1 C10 90.22(19) . . ?
C6 S2 C7 90.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        30.77
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.094
_database_code_depnum_ccdc_archive 'CCDC 967135'
