# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_she_270m

#_database_code_CSD                   'SHE270'
_database_code_depnum_ccdc_archive 'CCDC 1001644'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H15 Sb Se'
_chemical_formula_sum            'C6 H15 Sb Se'
_chemical_formula_weight         287.89

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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   P63mc

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

_cell_length_a                   9.2201(11)
_cell_length_b                   9.2201(11)
_cell_length_c                   6.5289(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     480.66(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    8830
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      31.89

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.989
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    6.578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   
; 
 BRUKER AXS SMART APEX 2 Vers. 3.0-2009
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_measurement_device_type  
; 
 Bruker D8 KAPPA series II with APEX II area detector system
;
_diffrn_measurement_method       
;
 Data collection strategy APEX 2/COSMO
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            9591
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0103
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         32.05
_reflns_number_total             596
_reflns_number_gt                589
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_cell_refinement       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_data_reduction        'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_structure_solution    'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_structure_refinement  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_molecular_graphics    'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'

_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. 
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
 The methyl groups are idealized with
 tetrahedral angles in a combined 
 rotating and rigid group refinement
 with the 1.5 fold isotropic displacement
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
 Refinement as racemic twinning with matrix -1 0 0 0 -1 0 0 0 -1 2 
 with Flack absolute structure parameter 0.622(17) in the final 
 structure factor calculation
 Carbon atom C(1)disordered about a mirror plane over 
 two sites with occupancies factor 0.5 
 together with the riding hydrogen atoms.
;

_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)+(0.0289P)²+0.3913P] 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   0.622(17)
_chemical_absolute_configuration .
_refine_ls_number_reflns         596
_refine_ls_number_parameters     23
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0197
_refine_ls_R_factor_gt           0.0195
_refine_ls_wR_factor_ref         0.0495
_refine_ls_wR_factor_gt          0.0494
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_restrained_S_all      1.227
_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
Sb1 Sb 0.3333 0.6667 0.07071(5) 0.01165(9) Uani 1 6 d S . .
Se1 Se 0.3333 0.6667 0.43926(12) 0.01805(14) Uani 1 6 d S . .
C1 C 0.2737(6) 0.4281(6) -0.0534(7) 0.0165(7) Uani 0.50 1 d P . .
H1A H 0.3732 0.4190 -0.0495 0.020 Uiso 0.50 1 d PR . .
H1B H 0.2426 0.4242 -0.1948 0.020 Uiso 0.50 1 d PR . .
C2 C 0.1432(2) 0.2863(5) 0.0526(8) 0.0327(9) Uani 1 2 d S . .
H2A H 0.0599 0.1861 -0.0125 0.049 Uiso 0.25 1 d PR A 1
H2B H 0.2502 0.2933 0.0461 0.049 Uiso 0.25 1 d PR A 1
H2C H 0.1128 0.2877 0.1934 0.049 Uiso 0.25 1 d PR A 1
H2D H 0.1251 0.1861 -0.0125 0.049 Uiso 0.25 1 d PR A 2
H2E H 0.1738 0.2877 0.1934 0.049 Uiso 0.25 1 d PR A 2
H2F H 0.0419 0.2933 0.0461 0.049 Uiso 0.25 1 d PR A 2

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
Sb1 0.01155(10) 0.01155(10) 0.01186(15) 0.000 0.000 0.00578(5)
Se1 0.0210(2) 0.0210(2) 0.0122(3) 0.000 0.000 0.01050(11)
C1 0.019(2) 0.0143(19) 0.017(2) -0.0015(16) 0.0019(16) 0.0089(17)
C2 0.0508(19) 0.0128(12) 0.0219(18) 0.0020(17) 0.0010(8) 0.0064(6)

_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
Sb1 C1 2.142(4) 3_565 ?
Sb1 C1 2.142(4) 9_565 ?
Sb1 C1 2.142(4) 8 ?
Sb1 C1 2.142(4) 2_665 ?
Sb1 C1 2.142(4) 7_665 ?
Sb1 C1 2.142(4) . ?
Sb1 Se1 2.4062(8) . ?
C1 C1 1.100(10) 8 ?
C1 C2 1.436(6) . ?
C2 C1 1.436(6) 8 ?

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 Sb1 C1 29.8(3) 3_565 9_565 ?
C1 Sb1 C1 79.9(3) 3_565 8 ?
C1 Sb1 C1 106.58(14) 9_565 8 ?
C1 Sb1 C1 106.58(14) 3_565 2_665 ?
C1 Sb1 C1 79.9(3) 9_565 2_665 ?
C1 Sb1 C1 127.9(3) 8 2_665 ?
C1 Sb1 C1 127.9(3) 3_565 7_665 ?
C1 Sb1 C1 106.58(14) 9_565 7_665 ?
C1 Sb1 C1 106.58(14) 8 7_665 ?
C1 Sb1 C1 29.8(3) 2_665 7_665 ?
C1 Sb1 C1 106.58(14) 3_565 . ?
C1 Sb1 C1 127.9(3) 9_565 . ?
C1 Sb1 C1 29.8(3) 8 . ?
C1 Sb1 C1 106.58(14) 2_665 . ?
C1 Sb1 C1 79.9(3) 7_665 . ?
C1 Sb1 Se1 112.23(13) 3_565 . ?
C1 Sb1 Se1 112.23(13) 9_565 . ?
C1 Sb1 Se1 112.23(13) 8 . ?
C1 Sb1 Se1 112.23(13) 2_665 . ?
C1 Sb1 Se1 112.23(13) 7_665 . ?
C1 Sb1 Se1 112.23(13) . . ?
C1 C1 C2 67.5(2) 8 . ?
C1 C1 Sb1 75.12(13) 8 . ?
C2 C1 Sb1 114.9(3) . . ?
C1 C2 C1 45.0(4) 8 . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        32.05
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         2.125
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.119
#######################################################################
#
#                 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_she_276_twin4

#_database_code_CSD                   'SHE276'
_database_code_depnum_ccdc_archive 'CCDC 1001645'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H15 Br2 Sb'
_chemical_formula_weight         368.75

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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   11.5607(6)
_cell_length_b                   10.8911(6)
_cell_length_c                   8.6408(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.575(3)
_cell_angle_gamma                90.00
_cell_volume                     1080.80(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      30.5

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    9.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1277
_exptl_absorpt_correction_T_max  0.4330
_exptl_absorpt_process_details   
; 
 TWINABS - Bruker AXS scaling for twinned crystals - Version 2008/4
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_measurement_device_type  
; 
 Bruker D8 KAPPA series II with APEX II area detector system
;
_diffrn_measurement_method       
;
 Data collection strategy APEX 2/COSMO
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            65251
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         30.62
_reflns_number_total             3328
_reflns_number_gt                2856
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_cell_refinement       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_data_reduction        'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_structure_solution    'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_structure_refinement  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_molecular_graphics    'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'

_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. 

 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
 The methyl groups are idealized with
 tetrahedral angles in a combined 
 rotating and rigid group refinement
 with the 1.5 fold isotropic displacement
 parameters of the equivalent Uij of the 
 corresponding carbon atom.

 The crystal was a non-merohedral twin of four components. Refinement 
 was carried out using HKLF 4 data from twinabs
;

_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)+(0.0174P)²+1.4831P] 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         3328
_refine_ls_number_parameters     85
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0473
_refine_ls_wR_factor_gt          0.0451
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.002
_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
Sb1 Sb 0.731022(14) 0.011232(15) 0.158146(19) 0.01359(5) Uani 1 1 d . . .
Br1 Br 0.88081(2) 0.19229(2) 0.22715(3) 0.02320(7) Uani 1 1 d . . .
Br2 Br 0.58601(3) -0.17575(3) 0.09773(4) 0.02860(7) Uani 1 1 d . . .
C1 C 0.7289(2) 0.0483(3) -0.0838(3) 0.0196(5) Uani 1 1 d . . .
H1A H 0.6498 0.0335 -0.1375 0.023 Uiso 1 1 calc R . .
H1B H 0.7488 0.1356 -0.0989 0.023 Uiso 1 1 calc R . .
C2 C 0.8147(4) -0.0324(4) -0.1528(4) 0.0492(11) Uani 1 1 d . . .
H2A H 0.8907 -0.0263 -0.0903 0.074 Uiso 1 1 calc R . .
H2B H 0.8218 -0.0060 -0.2597 0.074 Uiso 1 1 calc R . .
H2C H 0.7877 -0.1177 -0.1535 0.074 Uiso 1 1 calc R . .
C3 C 0.6104(2) 0.0989(3) 0.2917(3) 0.0215(6) Uani 1 1 d . . .
H3A H 0.6089 0.1879 0.2681 0.026 Uiso 1 1 calc R . .
H3B H 0.5316 0.0658 0.2597 0.026 Uiso 1 1 calc R . .
C4 C 0.6397(3) 0.0813(3) 0.4665(3) 0.0267(6) Uani 1 1 d . . .
H4A H 0.6363 -0.0063 0.4917 0.040 Uiso 1 1 calc R . .
H4B H 0.5833 0.1263 0.5214 0.040 Uiso 1 1 calc R . .
H4C H 0.7182 0.1125 0.4989 0.040 Uiso 1 1 calc R . .
C5 C 0.8626(2) -0.1136(2) 0.2524(3) 0.0191(5) Uani 1 1 d . . .
H5A H 0.8450 -0.1961 0.2077 0.023 Uiso 1 1 calc R . .
H5B H 0.9383 -0.0872 0.2206 0.023 Uiso 1 1 calc R . .
C6 C 0.8732(3) -0.1224(3) 0.4284(3) 0.0256(6) Uani 1 1 d . . .
H6A H 0.8917 -0.0413 0.4737 0.038 Uiso 1 1 calc R . .
H6B H 0.9355 -0.1802 0.4646 0.038 Uiso 1 1 calc R . .
H6C H 0.7994 -0.1514 0.4607 0.038 Uiso 1 1 calc R . .

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
Sb1 0.01273(7) 0.01446(8) 0.01362(8) -0.00004(6) 0.00170(5) 0.00087(6)
Br1 0.01985(13) 0.01965(14) 0.02977(15) -0.00481(11) 0.00137(11) -0.00425(10)
Br2 0.02459(15) 0.02388(15) 0.03763(18) -0.00122(12) 0.00492(13) -0.01010(11)
C1 0.0191(12) 0.0239(13) 0.0153(12) 0.0038(10) 0.0005(10) -0.0006(10)
C2 0.074(3) 0.053(2) 0.0250(17) 0.0084(16) 0.0221(18) 0.035(2)
C3 0.0149(12) 0.0270(14) 0.0229(14) -0.0031(11) 0.0032(10) 0.0060(10)
C4 0.0258(14) 0.0331(16) 0.0220(14) -0.0019(12) 0.0061(12) 0.0100(12)
C5 0.0185(12) 0.0193(13) 0.0196(13) 0.0000(10) 0.0033(10) 0.0055(10)
C6 0.0261(14) 0.0310(16) 0.0195(14) 0.0035(12) 0.0009(11) 0.0113(12)

_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
Sb1 C1 2.127(3) . ?
Sb1 C5 2.131(3) . ?
Sb1 C3 2.134(3) . ?
Sb1 Br1 2.6469(3) . ?
Sb1 Br2 2.6513(3) . ?
C1 C2 1.500(4) . ?
C3 C4 1.522(4) . ?
C5 C6 1.515(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 Sb1 C5 115.10(10) . . ?
C1 Sb1 C3 120.78(11) . . ?
C5 Sb1 C3 124.10(10) . . ?
C1 Sb1 Br1 90.77(8) . . ?
C5 Sb1 Br1 88.25(8) . . ?
C3 Sb1 Br1 89.77(8) . . ?
C1 Sb1 Br2 90.95(8) . . ?
C5 Sb1 Br2 89.58(8) . . ?
C3 Sb1 Br2 90.72(8) . . ?
Br1 Sb1 Br2 177.655(12) . . ?
C2 C1 Sb1 110.2(2) . . ?
C4 C3 Sb1 113.31(18) . . ?
C6 C5 Sb1 113.33(17) . . ?

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
C5 Sb1 C1 C2 6.2(3) . . . . ?
C3 Sb1 C1 C2 -175.1(2) . . . . ?
Br1 Sb1 C1 C2 94.7(2) . . . . ?
Br2 Sb1 C1 C2 -83.7(2) . . . . ?
C1 Sb1 C3 C4 -168.6(2) . . . . ?
C5 Sb1 C3 C4 9.9(3) . . . . ?
Br1 Sb1 C3 C4 -77.8(2) . . . . ?
Br2 Sb1 C3 C4 99.9(2) . . . . ?
C1 Sb1 C5 C6 171.07(19) . . . . ?
C3 Sb1 C5 C6 -7.5(3) . . . . ?
Br1 Sb1 C5 C6 81.0(2) . . . . ?
Br2 Sb1 C5 C6 -98.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.62
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.746
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.114
#######################################################################
#
#                 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_she_sbs

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H15 S Sb'
_chemical_formula_weight         240.99

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   P31c

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

_cell_length_a                   9.2365(5)
_cell_length_b                   9.2365(5)
_cell_length_c                   6.3367(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     468.18(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    1589
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.72

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             236
_exptl_absorpt_coefficient_mu    3.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   
; 
 BRUKER AXS SMART APEX 2 Vers. 3.0-2009
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;

_exptl_special_details           
; 
 The crystallization was performed on the diffractometer at a temperature of 
 170 K with a miniature zone melting procedure using focussed infrared-laser- 
 radiation according to: R. Boese, M. Nussbaumer, "In Situ Crystallization 
 Techniques", in: "Organic Crystal Chemistry", 
 Ed. D.W. Jones, Oxford University Press, Oxford, England, (1994) 20-37 
;

_diffrn_ambient_temperature      150(1)
_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  
; 
 Siemens SMART three axis goniometer with APEX II area detector system
;
_diffrn_measurement_method       
;
 Data collection strategy APEX 2 / COSMO
 with chi = 0 deg, phi +/- 10 deg
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            2573
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         4.10
_diffrn_reflns_theta_max         24.98
_reflns_number_total             424
_reflns_number_gt                392
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER AXS SMART APEX 2 Vers. 3.0-2009'
_computing_cell_refinement       'BRUKER AXS SMART APEX 2 Vers. 3.0-2009'
_computing_data_reduction        'BRUKER AXS SMART APEX 2 Vers. 3.0-2009'
_computing_structure_solution    'BRUKER AXS SMART APEX 2 Vers. 3.0-2009'
_computing_structure_refinement  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_molecular_graphics    'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'

_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. 
 Treatment of hydrogen atoms    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
 The methyl groups are idealized with
 tetrahedral angles in a combined 
 rotating and rigid group refinement
 with the 1.5 fold isotropic displacement
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;

_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)+(0.0528P)²+0.1621P] 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   0.39(14)
_refine_ls_number_reflns         424
_refine_ls_number_parameters     25
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.154
_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
Sb1 Sb 0.6667 0.3333 0.2779 0.0271(3) Uani 1 3 d S . .
S1 S 0.6667 0.3333 0.6537(10) 0.0414(9) Uani 1 3 d S . .
C1 C 0.4300(17) 0.1496(15) 0.157(3) 0.070(4) Uani 1 1 d . . .
H1A H 0.4198 0.1752 0.0078 0.084 Uiso 1 1 d R . .
H1B H 0.4210 0.0382 0.1620 0.084 Uiso 1 1 d R . .
C2 C 0.2906(8) 0.147(4) 0.286(5) 0.050(3) Uani 1 1 d . . .
H2A H 0.3112 0.1398 0.4359 0.075 Uiso 1 1 d R . .
H2B H 0.1838 0.0495 0.2451 0.075 Uiso 1 1 d R . .
H2C H 0.2866 0.2493 0.2589 0.075 Uiso 1 1 d R . .

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
Sb1 0.0193(3) 0.0193(3) 0.0428(7) 0.000 0.000 0.00966(14)
S1 0.0370(13) 0.0370(13) 0.050(3) 0.000 0.000 0.0185(7)
C1 0.068(8) 0.044(6) 0.094(13) -0.009(6) -0.015(7) 0.025(6)
C2 0.017(3) 0.056(11) 0.068(8) -0.008(8) -0.009(13) 0.013(10)

_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
Sb1 C1 2.130(13) . ?
Sb1 C1 2.130(13) 2_655 ?
Sb1 C1 2.130(13) 3_665 ?
Sb1 S1 2.381(7) . ?
C1 C2 1.51(3) . ?

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 Sb1 C1 107.8(5) . 2_655 ?
C1 Sb1 C1 107.8(5) . 3_665 ?
C1 Sb1 C1 107.8(5) 2_655 3_665 ?
C1 Sb1 S1 111.1(5) . . ?
C1 Sb1 S1 111.1(5) 2_655 . ?
C1 Sb1 S1 111.1(5) 3_665 . ?
C2 C1 Sb1 110.2(13) . . ?

_diffrn_measured_fraction_theta_max 0.819
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.819
_refine_diff_density_max         1.437
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.118
_vrf_PLAT029_she_sbs             
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......       0.82      
RESPONSE: 
 The compound is liquid at RT. The single crystal
 is formed by an in-situ zone melting process inside
 a quartz capillary using an IR-laser. 
 The experimental setup does only allow for a
 omega scan of the single crystal. This limits the
 completeness to 75% to 90% depending on the 
 crystal system.
;
_database_code_depnum_ccdc_archive 'CCDC 1001646'
