# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2004


data_global

_journal_coden_Cambridge         440

loop_
_publ_author_name
'Robert Davies'
'Gabriel A. Asseily'
'Henry S. Rzepa'
'Andrew J. P. White'

_publ_contact_author_name        'Dr Rob Davies'
_publ_contact_author_address     
;
Dept of Chemistry
Imperial College London
Exhibition Road
London
SW7 2AZ
UNITED KINGDOM
;

_publ_contact_author_email       R.DAVIES@IMPERIAL.AC.UK

_publ_requested_journal          'New Journal of Chemistry'

_publ_section_title              
;
A Solid-State Structural and Theoretical Study on
the 1:1 Addition Compounds of Thioethers with Dihalogens and
Interhalogens I-X (X = I, Br, Cl)
;

data_Compound_1
_database_code_depnum_ccdc_archive 'CCDC 225279'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Cl I S'
_chemical_formula_weight         376.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   6.956(2)
_cell_length_b                   5.6659(10)
_cell_length_c                   18.636(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.90(2)
_cell_angle_gamma                90.00
_cell_volume                     725.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      10.76
_cell_measurement_theta_max      28.71

_exptl_crystal_description       needles
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    20.171
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.2369
_exptl_absorpt_correction_T_max  0.6976
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      183(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker P4/RA'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1420
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         62.93
_reflns_number_total             1305
_reflns_number_gt                1249
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0387P)^2^+1.6846P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(15)
_refine_ls_number_reflns         1305
_refine_ls_number_parameters     143
_refine_ls_number_restraints     365
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      0.949
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#Results of chirality/polarity tests
#_refine_ls_R_factor_obs+      0.0346
#_refine_ls_wR_factor_obs+       0.0836
#_refine_ls_abs_structure_Flack+ 0.00(3)
#_refine_ls_R_factor_obs-         0.0430
#_refine_ls_wR_factor_obs-        0.1028
#_refine_ls_abs_structure_Flack-  1.00(3)

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
I I 0.37092(7) 0.44712(16) 0.72488(3) 0.02897(19) Uani 1 1 d . . .
Cl Cl 0.1520(4) 0.7977(5) 0.74318(17) 0.0539(7) Uani 1 1 d . . .
S S 0.6109(3) 0.1104(4) 0.71079(11) 0.0272(4) Uani 1 1 d . B .
C1 C 0.8139(11) 0.2807(19) 0.6876(4) 0.0294(19) Uani 1 1 d . . .
H1A H 0.8210 0.4349 0.7129 0.035 Uiso 1 1 calc R . .
H1B H 0.9373 0.1952 0.7035 0.035 Uiso 1 1 calc R . .
C2 C 0.7013(9) 0.5247(9) 0.5751(3) 0.031(2) Uani 1 1 d G . .
H2A H 0.6615 0.6451 0.6051 0.037 Uiso 1 1 calc R . .
C3 C 0.6743(8) 0.5537(8) 0.5001(3) 0.0310(19) Uani 1 1 d G . .
H3A H 0.6160 0.6939 0.4789 0.037 Uiso 1 1 calc R . .
C4 C 0.7326(8) 0.3776(10) 0.4562(2) 0.029(2) Uani 1 1 d G . .
H4A H 0.7141 0.3975 0.4050 0.035 Uiso 1 1 calc R . .
C5 C 0.8179(8) 0.1725(9) 0.4873(3) 0.031(2) Uani 1 1 d G . .
H5A H 0.8578 0.0521 0.4573 0.037 Uiso 1 1 calc R . .
C6 C 0.8450(8) 0.1434(8) 0.5622(3) 0.0298(19) Uani 1 1 d G . .
H6A H 0.9033 0.0032 0.5834 0.036 Uiso 1 1 calc R . .
C7 C 0.7867(9) 0.3195(10) 0.6061(2) 0.0262(18) Uani 1 1 d G . .
C8 C 0.6997(13) 0.0160(17) 0.8037(5) 0.034(2) Uani 1 1 d D . .
H8A H 0.6060 -0.0985 0.8188 0.041 Uiso 0.60 1 calc PR A 1
H8B H 0.8251 -0.0671 0.8044 0.041 Uiso 0.60 1 calc PR A 1
H8C H 0.8082 -0.0880 0.8027 0.041 Uiso 0.40 1 d PR A 2
H8D H 0.5987 -0.0738 0.8207 0.041 Uiso 0.40 1 d PR A 2
C9 C 0.5824(14) 0.267(2) 0.8992(6) 0.030(3) Uani 0.60 1 d PGDU B 1
H9A H 0.4659 0.1764 0.8929 0.036 Uiso 0.60 1 calc PR B 1
C10 C 0.6066(15) 0.451(2) 0.9489(6) 0.048(4) Uani 0.60 1 d PGU B 1
H10A H 0.5066 0.4873 0.9766 0.057 Uiso 0.60 1 calc PR B 1
C11 C 0.7770(17) 0.583(2) 0.9581(6) 0.046(4) Uani 0.60 1 d PGU B 1
H11A H 0.7936 0.7095 0.9921 0.055 Uiso 0.60 1 calc PR B 1
C12 C 0.9234(14) 0.5307(19) 0.9176(6) 0.044(4) Uani 0.60 1 d PGU B 1
H12A H 1.0399 0.6209 0.9239 0.053 Uiso 0.60 1 calc PR B 1
C13 C 0.8992(13) 0.346(2) 0.8679(6) 0.037(3) Uani 0.60 1 d PGDU B 1
H13A H 0.9992 0.3101 0.8402 0.045 Uiso 0.60 1 calc PR B 1
C14 C 0.7287(15) 0.214(2) 0.8587(6) 0.037(4) Uani 0.60 1 d PGDU B 1
C9' C 0.636(2) 0.289(3) 0.9027(11) 0.040(6) Uiso 0.40 1 d PGDU B 2
H9'A H 0.5128 0.2160 0.9016 0.047 Uiso 0.40 1 calc PR B 2
C10' C 0.687(3) 0.482(3) 0.9478(11) 0.045(6) Uiso 0.40 1 d PGU B 2
H10B H 0.5983 0.5406 0.9775 0.055 Uiso 0.40 1 calc PR B 2
C11' C 0.867(3) 0.589(3) 0.9494(10) 0.047(6) Uiso 0.40 1 d PGU B 2
H11B H 0.9020 0.7208 0.9802 0.057 Uiso 0.40 1 calc PR B 2
C12' C 0.997(2) 0.503(3) 0.9059(10) 0.040(6) Uiso 0.40 1 d PGU B 2
H12B H 1.1203 0.5764 0.9070 0.048 Uiso 0.40 1 calc PR B 2
C13' C 0.946(2) 0.310(3) 0.8608(11) 0.039(5) Uiso 0.40 1 d PGDU B 2
H13B H 1.0348 0.2519 0.8311 0.047 Uiso 0.40 1 calc PR B 2
C14' C 0.766(2) 0.203(3) 0.8592(11) 0.026(5) Uiso 0.40 1 d PGDU B 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
I 0.0286(3) 0.0296(3) 0.0289(3) 0.0035(3) 0.00485(16) 0.0023(3)
Cl 0.0533(15) 0.0383(16) 0.0741(17) 0.0064(14) 0.0221(13) 0.0159(13)
S 0.0334(10) 0.0260(10) 0.0218(9) 0.0009(9) 0.0032(8) 0.0001(9)
C1 0.022(4) 0.044(5) 0.023(4) 0.001(4) 0.006(3) 0.000(4)
C2 0.029(5) 0.033(5) 0.030(4) -0.004(4) 0.004(4) 0.001(4)
C3 0.020(4) 0.041(5) 0.031(4) 0.013(4) -0.002(3) 0.000(4)
C4 0.032(4) 0.034(6) 0.020(3) 0.000(3) 0.000(3) -0.004(4)
C5 0.034(5) 0.036(5) 0.025(4) -0.008(4) 0.012(4) 0.000(4)
C6 0.019(4) 0.037(5) 0.035(4) 0.006(4) 0.009(3) 0.007(4)
C7 0.026(4) 0.033(5) 0.020(4) -0.001(4) 0.002(3) 0.007(4)
C8 0.042(5) 0.037(5) 0.026(4) 0.006(4) 0.010(4) 0.007(4)
C9 0.033(6) 0.037(6) 0.018(5) -0.003(5) -0.004(5) -0.003(5)
C10 0.059(9) 0.057(8) 0.026(6) -0.006(9) 0.001(6) 0.011(11)
C11 0.039(8) 0.056(9) 0.035(7) -0.001(7) -0.019(7) -0.001(8)
C12 0.028(7) 0.059(9) 0.047(8) 0.003(7) 0.014(7) 0.014(7)
C13 0.037(6) 0.042(6) 0.029(6) 0.002(5) -0.008(5) 0.015(6)
C14 0.035(6) 0.044(7) 0.027(6) 0.001(5) -0.010(5) 0.004(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
I Cl 2.558(3) . ?
I S 2.575(2) . ?
S C1 1.817(9) . ?
S C8 1.827(9) . ?
C1 C7 1.517(8) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C8 C14' 1.504(13) . ?
C8 C14 1.512(11) . ?
C9 C10 1.3900 . ?
C9 C14 1.3900 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C9' C10' 1.3900 . ?
C9' C14' 1.3900 . ?
C10' C11' 1.3900 . ?
C11' C12' 1.3900 . ?
C12' C13' 1.3900 . ?
C13' C14' 1.3900 . ?

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
Cl I S 176.14(9) . . ?
C1 S C8 102.7(4) . . ?
C1 S I 99.8(3) . . ?
C8 S I 104.5(3) . . ?
C7 C1 S 109.5(5) . . ?
C3 C2 C7 120.0 . . ?
C2 C3 C4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C4 C5 C6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 C1 118.8(5) . . ?
C2 C7 C1 121.1(5) . . ?
C14' C8 C14 10.0(8) . . ?
C14' C8 S 117.9(12) . . ?
C14 C8 S 114.5(8) . . ?
C10 C9 C14 120.0 . . ?
C9 C10 C11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C11 C12 C13 120.0 . . ?
C14 C13 C12 120.0 . . ?
C13 C14 C9 120.0 . . ?
C13 C14 C8 120.3(6) . . ?
C9 C14 C8 119.7(6) . . ?
C10' C9' C14' 120.0 . . ?
C11' C10' C9' 120.0 . . ?
C10' C11' C12' 120.0 . . ?
C13' C12' C11' 120.0 . . ?
C14' C13' C12' 120.0 . . ?
C13' C14' C9' 120.0 . . ?
C13' C14' C8 120.1(7) . . ?
C9' C14' C8 119.4(7) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        62.93
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.113

data_Compound_2
_database_code_depnum_ccdc_archive 'CCDC 225280'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 Br I S'
_chemical_formula_weight         421.12

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   7.1678(6)
_cell_length_b                   5.7376(11)
_cell_length_c                   18.5292(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.495(7)
_cell_angle_gamma                90.00
_cell_volume                     749.28(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    27
_cell_measurement_theta_min      4.82
_cell_measurement_theta_max      12.45

_exptl_crystal_description       'blocky needles'
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    4.920
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.4989
_exptl_absorpt_correction_T_max  0.8404
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      183(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 P4'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        8.49
_diffrn_reflns_number            1581
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1460
_reflns_number_gt                1348
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Results of chirality/polarity tests
#_refine_ls_R_factor_obs+         0.0264
#_refine_ls_wR_factor_obs+        0.0529
#_refine_ls_abs_structure_Flack+  0.00(4)
#_refine_ls_R_factor_obs-         0.0306
#_refine_ls_wR_factor_obs-        0.0628
#_refine_ls_abs_structure_Flack-  1.00(4)
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0165P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_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   -0.001(19)
_refine_ls_number_reflns         1460
_refine_ls_number_parameters     143
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0542
_refine_ls_wR_factor_gt          0.0529
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.057
_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
I I 0.11434(6) 0.33761(10) 0.27458(2) 0.02748(10) Uani 1 1 d . . .
Br Br 0.33585(13) 0.69715(13) 0.25049(7) 0.0528(3) Uani 1 1 d . . .
S S -0.1260(2) 0.0059(3) 0.28968(9) 0.0257(3) Uani 1 1 d . A .
C1 C -0.3217(10) 0.1830(14) 0.3114(4) 0.0329(15) Uani 1 1 d . . .
H1A H -0.3274 0.3336 0.2850 0.039 Uiso 1 1 calc R . .
H1B H -0.4437 0.1008 0.2954 0.039 Uiso 1 1 calc R . .
C2 C -0.2027(7) 0.4277(6) 0.4243(2) 0.0275(14) Uani 1 1 d G . .
H2A H -0.1636 0.5440 0.3937 0.033 Uiso 1 1 calc R . .
C3 C -0.1726(6) 0.4598(6) 0.4999(2) 0.0320(15) Uani 1 1 d G . .
H3A H -0.1130 0.5979 0.5210 0.038 Uiso 1 1 calc R . .
C4 C -0.2298(6) 0.2897(8) 0.54467(18) 0.0294(16) Uani 1 1 d G . .
H4A H -0.2092 0.3116 0.5963 0.035 Uiso 1 1 calc R . .
C5 C -0.3170(6) 0.0876(7) 0.5138(2) 0.0314(14) Uani 1 1 d G . .
H5A H -0.3561 -0.0286 0.5444 0.038 Uiso 1 1 calc R . .
C6 C -0.3471(6) 0.0555(6) 0.4383(2) 0.0291(14) Uani 1 1 d G . .
H6A H -0.4067 -0.0826 0.4172 0.035 Uiso 1 1 calc R . .
C7 C -0.2899(7) 0.2256(8) 0.39349(18) 0.0274(14) Uani 1 1 d G . .
C8 C -0.2160(10) -0.0878(12) 0.1953(4) 0.0295(15) Uani 1 1 d D . .
H8A H -0.1278 -0.2058 0.1816 0.035 Uiso 0.89(3) 1 calc PR A 1
H8B H -0.3400 -0.1652 0.1939 0.035 Uiso 0.89(3) 1 calc PR A 1
H8C H -0.1187 -0.1883 0.1794 0.035 Uiso 0.11(3) 1 d PR A 2
H8D H -0.3299 -0.1854 0.1953 0.035 Uiso 0.11(3) 1 d PR A 2
C9 C -0.0991(14) 0.1450(15) 0.0973(4) 0.044(2) Uani 0.89(3) 1 d PGD A 1
H9A H 0.0113 0.0500 0.1045 0.053 Uiso 0.89(3) 1 calc PR A 1
C10 C -0.1182(18) 0.3261(17) 0.0467(4) 0.064(4) Uani 0.89(3) 1 d PG A 1
H10A H -0.0208 0.3548 0.0192 0.077 Uiso 0.89(3) 1 calc PR A 1
C11 C -0.280(2) 0.4651(14) 0.0362(4) 0.068(5) Uani 0.89(3) 1 d PG A 1
H11A H -0.2927 0.5888 0.0016 0.082 Uiso 0.89(3) 1 calc PR A 1
C12 C -0.4221(17) 0.4230(13) 0.0765(5) 0.060(5) Uani 0.89(3) 1 d PG A 1
H12A H -0.5324 0.5180 0.0693 0.072 Uiso 0.89(3) 1 calc PR A 1
C13 C -0.4030(13) 0.2420(14) 0.1271(4) 0.047(3) Uani 0.89(3) 1 d PGD A 1
H13A H -0.5003 0.2132 0.1546 0.056 Uiso 0.89(3) 1 calc PR A 1
C14 C -0.2415(13) 0.1029(12) 0.1375(4) 0.037(2) Uani 0.89(3) 1 d PGD A 1
C9' C -0.163(6) 0.183(7) 0.094(2) 0.018(16) Uiso 0.11(3) 1 d PGD A 2
H9'A H -0.0448 0.1082 0.0940 0.021 Uiso 0.11(3) 1 calc PR A 2
C10' C -0.219(9) 0.369(7) 0.047(2) 0.025(16) Uiso 0.11(3) 1 d PG A 2
H10B H -0.1386 0.4212 0.0147 0.030 Uiso 0.11(3) 1 calc PR A 2
C11' C -0.392(10) 0.479(6) 0.047(2) 0.06(3) Uiso 0.11(3) 1 d PG A 2
H11B H -0.4296 0.6056 0.0149 0.067 Uiso 0.11(3) 1 calc PR A 2
C12' C -0.509(8) 0.402(6) 0.094(3) 0.024(15) Uiso 0.11(3) 1 d PG A 2
H12B H -0.6270 0.4771 0.0945 0.029 Uiso 0.11(3) 1 calc PR A 2
C13' C -0.453(6) 0.216(8) 0.142(3) 0.027(17) Uiso 0.11(3) 1 d PGD A 2
H13B H -0.5332 0.1642 0.1738 0.032 Uiso 0.11(3) 1 calc PR A 2
C14' C -0.280(6) 0.107(9) 0.141(3) 0.03(2) Uiso 0.11(3) 1 d PGD 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
I 0.02220(15) 0.02311(17) 0.03833(18) -0.0041(2) 0.00865(12) -0.0018(2)
Br 0.0418(4) 0.0311(4) 0.0928(7) -0.0085(4) 0.0317(5) -0.0131(4)
S 0.0276(7) 0.0206(7) 0.0297(8) 0.0014(6) 0.0077(6) -0.0017(7)
C1 0.030(3) 0.031(4) 0.039(4) 0.005(3) 0.008(3) -0.001(3)
C2 0.018(3) 0.022(3) 0.043(4) -0.001(3) 0.010(3) 0.005(3)
C3 0.023(3) 0.030(4) 0.041(4) -0.008(3) 0.001(3) 0.000(3)
C4 0.023(3) 0.030(5) 0.036(3) -0.006(3) 0.007(2) 0.002(2)
C5 0.025(3) 0.033(3) 0.039(4) 0.002(3) 0.012(3) 0.003(3)
C6 0.022(3) 0.027(4) 0.040(4) -0.004(3) 0.009(3) -0.006(3)
C7 0.018(3) 0.025(3) 0.042(4) 0.001(3) 0.012(3) 0.001(3)
C8 0.030(3) 0.024(3) 0.035(3) -0.004(3) 0.008(3) 0.000(3)
C9 0.039(6) 0.057(7) 0.039(5) 0.003(5) 0.013(4) 0.007(5)
C10 0.075(9) 0.078(8) 0.038(5) 0.018(8) 0.006(5) -0.013(11)
C11 0.099(13) 0.056(8) 0.044(6) 0.015(6) -0.004(7) 0.012(7)
C12 0.070(10) 0.049(6) 0.050(7) 0.001(5) -0.016(7) 0.011(6)
C13 0.043(6) 0.057(6) 0.037(6) -0.006(5) 0.000(5) 0.002(5)
C14 0.039(5) 0.034(5) 0.036(5) -0.015(4) 0.005(4) -0.008(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
I S 2.6159(18) . ?
I Br 2.6896(10) . ?
S C8 1.832(7) . ?
S C1 1.836(8) . ?
C1 C7 1.516(8) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C8 C14' 1.513(14) . ?
C8 C14 1.518(9) . ?
C9 C10 1.3900 . ?
C9 C14 1.3900 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C9' C10' 1.3900 . ?
C9' C14' 1.3900 . ?
C10' C11' 1.3900 . ?
C11' C12' 1.3900 . ?
C12' C13' 1.3900 . ?
C13' C14' 1.3900 . ?

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
S I Br 174.81(5) . . ?
C8 S C1 102.8(3) . . ?
C8 S I 103.6(2) . . ?
C1 S I 99.5(3) . . ?
C7 C1 S 109.2(5) . . ?
C3 C2 C7 120.0 . . ?
C4 C3 C2 120.0 . . ?
C3 C4 C5 120.0 . . ?
C4 C5 C6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 C1 118.6(4) . . ?
C2 C7 C1 121.4(4) . . ?
C14' C8 C14 11.4(10) . . ?
C14' C8 S 115(3) . . ?
C14 C8 S 115.9(5) . . ?
C10 C9 C14 120.0 . . ?
C9 C10 C11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C13 C12 C11 120.0 . . ?
C12 C13 C14 120.0 . . ?
C13 C14 C9 120.0 . . ?
C13 C14 C8 120.1(5) . . ?
C9 C14 C8 119.8(5) . . ?
C10' C9' C14' 120.0 . . ?
C9' C10' C11' 120.0 . . ?
C10' C11' C12' 120.0 . . ?
C13' C12' C11' 120.0 . . ?
C12' C13' C14' 120.0 . . ?
C13' C14' C9' 120.0 . . ?
C13' C14' C8 119.8(8) . . ?
C9' C14' C8 120.1(8) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.098

#===END