# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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# 
#  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. 
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#  fide research purposes only. It may contain copyright material 
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data_cd201215
_database_code_depnum_ccdc_archive 'CCDC 773956'
#TrackingRef 'cd201215.cif'
_audit_update_record             
;
2013-02-25 # Formatted by publCIF
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            
;14-chloro-7,14-dihydro-5H-benzo(c)naphtho(1,2-
f)(1,5)oxastibocine
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Cl O Sb'
_chemical_formula_weight         403.49
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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   P2(1)/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                   11.7504(10)
_cell_length_b                   14.4272(12)
_cell_length_c                   8.9688(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.251(2)
_cell_angle_gamma                90.00
_cell_volume                     1518.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      5.354
_cell_measurement_theta_max      56.175
_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    1.988
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6259
_exptl_absorpt_correction_T_max  0.8109
_exptl_absorpt_process_details   sadabs
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8803
_diffrn_reflns_av_R_equivalents  0.1210
_diffrn_reflns_av_sigmaI/netI    0.0836
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3307
_reflns_number_gt                2903
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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^)+(0.0479P)^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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0179(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3307
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_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
Sb Sb 0.305210(19) 0.567000(15) 0.91563(3) 0.03528(14) Uani 1 1 d . . .
Cl1 Cl 0.28650(9) 0.46997(8) 0.68740(12) 0.0526(3) Uani 1 1 d . . .
O1 O 0.3679(2) 0.69614(17) 1.0728(3) 0.0390(6) Uani 1 1 d . . .
C1 C 0.4784(3) 0.6007(2) 0.8606(4) 0.0336(7) Uani 1 1 d . . .
C2 C 0.5320(4) 0.5745(2) 0.7333(5) 0.0393(9) Uani 1 1 d . . .
H2 H 0.4923 0.5404 0.6594 0.047 Uiso 1 1 calc R . .
C3 C 0.6441(3) 0.5989(3) 0.7158(4) 0.0444(9) Uani 1 1 d . . .
H3 H 0.6790 0.5809 0.6298 0.053 Uiso 1 1 calc R . .
C4 C 0.7046(3) 0.6489(3) 0.8223(5) 0.0482(10) Uani 1 1 d . . .
H4 H 0.7797 0.6658 0.8083 0.058 Uiso 1 1 calc R . .
C5 C 0.6536(3) 0.6742(3) 0.9511(5) 0.0438(9) Uani 1 1 d . . .
H5 H 0.6946 0.7080 1.0242 0.053 Uiso 1 1 calc R . .
C6 C 0.5424(3) 0.6497(2) 0.9722(4) 0.0361(8) Uani 1 1 d . . .
C7 C 0.4855(3) 0.6764(3) 1.1105(4) 0.0406(9) Uani 1 1 d . . .
H7A H 0.4917 0.6263 1.1825 0.049 Uiso 1 1 calc R . .
H7B H 0.5224 0.7307 1.1550 0.049 Uiso 1 1 calc R . .
C8 C 0.3515(3) 0.7814(3) 0.9914(4) 0.0396(8) Uani 1 1 d . . .
H8A H 0.4190 0.7954 0.9382 0.047 Uiso 1 1 calc R . .
H8B H 0.3391 0.8318 1.0602 0.047 Uiso 1 1 calc R . .
C9 C 0.2500(3) 0.7720(3) 0.8822(4) 0.0365(8) Uani 1 1 d . . .
C10 C 0.1985(3) 0.8552(3) 0.8337(5) 0.0463(9) Uani 1 1 d . . .
H10 H 0.2260 0.9114 0.8712 0.056 Uiso 1 1 calc R . .
C11 C 0.1078(3) 0.8536(3) 0.7314(5) 0.0486(10) Uani 1 1 d . . .
H11 H 0.0767 0.9090 0.6953 0.058 Uiso 1 1 calc R . .
C12 C 0.0612(3) 0.7690(3) 0.6802(4) 0.0404(8) Uani 1 1 d . . .
C13 C -0.0353(3) 0.7657(3) 0.5800(5) 0.0499(10) Uani 1 1 d . . .
H13 H -0.0664 0.8209 0.5426 0.060 Uiso 1 1 calc R . .
C14 C -0.0843(3) 0.6836(3) 0.5362(5) 0.0515(11) Uani 1 1 d . . .
H14 H -0.1465 0.6828 0.4674 0.062 Uiso 1 1 calc R . .
C15 C -0.0404(3) 0.6012(3) 0.5955(5) 0.0490(10) Uani 1 1 d . . .
H15 H -0.0763 0.5455 0.5704 0.059 Uiso 1 1 calc R . .
C16 C 0.0547(3) 0.6012(3) 0.6901(5) 0.0423(9) Uani 1 1 d . . .
H16 H 0.0829 0.5450 0.7271 0.051 Uiso 1 1 calc R . .
C17 C 0.1111(3) 0.6836(3) 0.7330(4) 0.0365(8) Uani 1 1 d . . .
C18 C 0.2123(3) 0.6872(2) 0.8304(4) 0.0342(8) 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
Sb 0.0435(2) 0.02541(18) 0.0371(2) 0.00041(9) 0.00387(12) -0.00378(8)
Cl1 0.0564(6) 0.0432(6) 0.0570(6) -0.0197(5) -0.0085(5) 0.0023(4)
O1 0.0451(14) 0.0352(14) 0.0373(13) -0.0035(11) 0.0080(11) -0.0028(11)
C1 0.0424(18) 0.0245(16) 0.0337(17) 0.0019(15) 0.0022(14) 0.0056(14)
C2 0.052(2) 0.0304(19) 0.036(2) 0.0000(15) 0.0015(17) 0.0086(15)
C3 0.055(2) 0.038(2) 0.042(2) 0.0047(19) 0.0153(17) 0.0073(18)
C4 0.042(2) 0.045(2) 0.059(3) 0.004(2) 0.0114(18) 0.0015(17)
C5 0.045(2) 0.037(2) 0.049(2) -0.0036(18) 0.0009(17) -0.0027(16)
C6 0.047(2) 0.0246(17) 0.0363(18) 0.0009(15) 0.0007(15) 0.0003(14)
C7 0.045(2) 0.041(2) 0.0358(19) -0.0072(17) 0.0015(16) -0.0054(16)
C8 0.046(2) 0.0302(19) 0.044(2) -0.0068(17) 0.0088(16) -0.0019(15)
C9 0.0401(18) 0.0300(19) 0.0402(19) -0.0049(16) 0.0095(15) -0.0031(15)
C10 0.050(2) 0.0259(19) 0.064(3) -0.0086(19) 0.0123(19) 0.0027(16)
C11 0.051(2) 0.033(2) 0.062(3) 0.000(2) 0.0068(19) 0.0052(17)
C12 0.0418(19) 0.034(2) 0.046(2) -0.0029(17) 0.0099(16) 0.0058(15)
C13 0.048(2) 0.041(2) 0.061(3) 0.002(2) 0.0047(19) 0.0133(18)
C14 0.038(2) 0.058(3) 0.058(3) -0.009(2) 0.0002(18) 0.0056(18)
C15 0.039(2) 0.045(2) 0.063(3) -0.012(2) 0.0043(18) 0.0010(18)
C16 0.0376(19) 0.0326(19) 0.057(2) -0.0035(19) 0.0066(16) -0.0003(16)
C17 0.0369(18) 0.0315(19) 0.042(2) -0.0015(16) 0.0110(15) 0.0012(14)
C18 0.0397(18) 0.0259(17) 0.0379(19) -0.0005(15) 0.0116(15) 0.0001(13)
_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
Sb C18 2.165(3) . ?
Sb C1 2.176(4) . ?
Sb O1 2.425(2) . ?
Sb Cl1 2.4793(10) . ?
O1 C7 1.433(4) . ?
O1 C8 1.437(4) . ?
C1 C2 1.388(5) . ?
C1 C6 1.407(5) . ?
C2 C3 1.380(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.493(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.505(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C18 1.374(5) . ?
C9 C10 1.402(5) . ?
C10 C11 1.366(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.405(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.407(6) . ?
C12 C17 1.433(5) . ?
C13 C14 1.364(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.404(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.436(5) . ?
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
C18 Sb C1 101.55(13) . . ?
C18 Sb O1 73.77(11) . . ?
C1 Sb O1 72.74(11) . . ?
C18 Sb Cl1 98.12(10) . . ?
C1 Sb Cl1 88.81(10) . . ?
O1 Sb Cl1 157.43(7) . . ?
C7 O1 C8 112.9(3) . . ?
C7 O1 Sb 104.0(2) . . ?
C8 O1 Sb 109.53(19) . . ?
C2 C1 C6 118.2(3) . . ?
C2 C1 Sb 126.9(3) . . ?
C6 C1 Sb 114.9(2) . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.3(3) . . ?
C5 C6 C7 121.4(3) . . ?
C1 C6 C7 118.3(3) . . ?
O1 C7 C6 109.1(3) . . ?
O1 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
O1 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O1 C8 C9 109.4(3) . . ?
O1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
O1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C18 C9 C10 122.1(3) . . ?
C18 C9 C8 121.9(3) . . ?
C10 C9 C8 116.0(3) . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 121.5(4) . . ?
C11 C12 C17 119.6(3) . . ?
C13 C12 C17 118.8(3) . . ?
C14 C13 C12 121.6(4) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.7(4) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 121.9(4) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C12 117.3(3) . . ?
C16 C17 C18 124.0(3) . . ?
C12 C17 C18 118.6(3) . . ?
C9 C18 C17 118.5(3) . . ?
C9 C18 Sb 116.6(2) . . ?
C17 C18 Sb 124.7(2) . . ?
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
C18 Sb O1 C7 -145.7(2) . . . . ?
C1 Sb O1 C7 -37.7(2) . . . . ?
Cl1 Sb O1 C7 -74.2(3) . . . . ?
C18 Sb O1 C8 -24.8(2) . . . . ?
C1 Sb O1 C8 83.2(2) . . . . ?
Cl1 Sb O1 C8 46.7(3) . . . . ?
C18 Sb C1 C2 -93.7(3) . . . . ?
O1 Sb C1 C2 -162.5(3) . . . . ?
Cl1 Sb C1 C2 4.3(3) . . . . ?
C18 Sb C1 C6 90.2(3) . . . . ?
O1 Sb C1 C6 21.5(2) . . . . ?
Cl1 Sb C1 C6 -171.7(2) . . . . ?
C6 C1 C2 C3 -2.1(5) . . . . ?
Sb C1 C2 C3 -178.0(3) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 1.1(6) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C4 C5 C6 C1 -1.8(6) . . . . ?
C4 C5 C6 C7 -179.9(4) . . . . ?
C2 C1 C6 C5 2.9(5) . . . . ?
Sb C1 C6 C5 179.4(3) . . . . ?
C2 C1 C6 C7 -178.9(3) . . . . ?
Sb C1 C6 C7 -2.5(4) . . . . ?
C8 O1 C7 C6 -71.6(4) . . . . ?
Sb O1 C7 C6 47.0(3) . . . . ?
C5 C6 C7 O1 144.5(3) . . . . ?
C1 C6 C7 O1 -33.6(4) . . . . ?
C7 O1 C8 C9 146.5(3) . . . . ?
Sb O1 C8 C9 31.1(3) . . . . ?
O1 C8 C9 C18 -23.5(5) . . . . ?
O1 C8 C9 C10 158.1(3) . . . . ?
C18 C9 C10 C11 -0.2(6) . . . . ?
C8 C9 C10 C11 178.2(4) . . . . ?
C9 C10 C11 C12 3.7(6) . . . . ?
C10 C11 C12 C13 177.1(4) . . . . ?
C10 C11 C12 C17 -1.6(6) . . . . ?
C11 C12 C13 C14 -176.5(4) . . . . ?
C17 C12 C13 C14 2.3(6) . . . . ?
C12 C13 C14 C15 2.1(7) . . . . ?
C13 C14 C15 C16 -3.7(7) . . . . ?
C14 C15 C16 C17 0.9(7) . . . . ?
C15 C16 C17 C12 3.4(6) . . . . ?
C15 C16 C17 C18 -179.0(4) . . . . ?
C11 C12 C17 C16 173.9(4) . . . . ?
C13 C12 C17 C16 -4.9(6) . . . . ?
C11 C12 C17 C18 -3.8(5) . . . . ?
C13 C12 C17 C18 177.4(4) . . . . ?
C10 C9 C18 C17 -5.3(6) . . . . ?
C8 C9 C18 C17 176.5(3) . . . . ?
C10 C9 C18 Sb 178.9(3) . . . . ?
C8 C9 C18 Sb 0.6(5) . . . . ?
C16 C17 C18 C9 -170.4(4) . . . . ?
C12 C17 C18 C9 7.1(5) . . . . ?
C16 C17 C18 Sb 5.1(5) . . . . ?
C12 C17 C18 Sb -177.4(3) . . . . ?
C1 Sb C18 C9 -55.2(3) . . . . ?
O1 Sb C18 C9 12.8(3) . . . . ?
Cl1 Sb C18 C9 -145.7(3) . . . . ?
C1 Sb C18 C17 129.2(3) . . . . ?
O1 Sb C18 C17 -162.8(3) . . . . ?
Cl1 Sb C18 C17 38.8(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.314
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.146


data_dm11266
_database_code_depnum_ccdc_archive 'CCDC 827987'
#TrackingRef 'dm11266.cif'
_audit_update_record             
;
2011-06-01 # Formatted by publCIF
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Bi Cl O'
_chemical_formula_weight         490.72
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
_cell_length_a                   20.5263(19)
_cell_length_b                   15.8560(15)
_cell_length_c                   4.5578(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1483.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    6900
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      30.44
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    12.060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1332
_exptl_absorpt_correction_T_max  0.3785
_exptl_absorpt_process_details   sadabs
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(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 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10320
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         26.99
_reflns_number_total             3079
_reflns_number_gt                2784
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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^)+(0.0000P)^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    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   -0.006(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3079
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0190
_refine_ls_R_factor_gt           0.0154
_refine_ls_wR_factor_ref         0.0365
_refine_ls_wR_factor_gt          0.0354
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_refine_ls_shift/su_max          0.003
_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
Bi1 Bi 0.275140(5) 0.082568(7) 0.24741(8) 0.01483(4) Uani 1 1 d . . .
Cl1 Cl 0.31619(5) -0.04972(6) 0.5204(2) 0.0239(2) Uani 1 1 d . . .
O1 O 0.21487(9) 0.22297(14) 0.2308(12) 0.0162(5) Uani 1 1 d . . .
C1 C 0.17939(19) 0.0724(2) 0.5023(8) 0.0157(8) Uani 1 1 d . . .
C2 C 0.16489(17) 0.0070(2) 0.6985(11) 0.0176(10) Uani 1 1 d . . .
H2 H 0.1976 -0.0324 0.7527 0.021 Uiso 1 1 calc R . .
C3 C 0.1017(2) -0.0001(3) 0.8146(7) 0.0217(10) Uani 1 1 d . . .
H3 H 0.0916 -0.0445 0.9470 0.026 Uiso 1 1 calc R . .
C4 C 0.05434(16) 0.0572(2) 0.7369(15) 0.0202(7) Uani 1 1 d . . .
H4 H 0.0118 0.0522 0.8170 0.024 Uiso 1 1 calc R . .
C5 C 0.06819(18) 0.1225(3) 0.5419(8) 0.0193(8) Uani 1 1 d . . .
H5 H 0.0351 0.1613 0.4866 0.023 Uiso 1 1 calc R . .
C6 C 0.13111(19) 0.1305(2) 0.4286(8) 0.0164(8) Uani 1 1 d . . .
C7 C 0.14634(15) 0.2019(2) 0.2215(16) 0.0197(8) Uani 1 1 d . . .
H7A H 0.1342 0.1854 0.0193 0.024 Uiso 1 1 calc R . .
H7B H 0.1203 0.2520 0.2763 0.024 Uiso 1 1 calc R . .
C8 C 0.23015(17) 0.2698(2) 0.4978(9) 0.0173(8) Uani 1 1 d . . .
H8A H 0.1988 0.2544 0.6540 0.021 Uiso 1 1 calc R . .
H8B H 0.2259 0.3311 0.4598 0.021 Uiso 1 1 calc R . .
C9 C 0.29805(18) 0.2507(3) 0.5985(8) 0.0160(7) Uani 1 1 d . . .
C10 C 0.32882(18) 0.3119(2) 0.7800(12) 0.0178(10) Uani 1 1 d . . .
H10 H 0.3063 0.3624 0.8281 0.021 Uiso 1 1 calc R . .
C11 C 0.3899(2) 0.2992(3) 0.8856(9) 0.0224(9) Uani 1 1 d . . .
H11 H 0.4086 0.3390 1.0164 0.027 Uiso 1 1 calc R . .
C12 C 0.42568(18) 0.2270(2) 0.8018(8) 0.0185(10) Uani 1 1 d . . .
C13 C 0.4916(2) 0.2144(3) 0.8938(9) 0.0236(9) Uani 1 1 d . . .
H13 H 0.5105 0.2528 1.0292 0.028 Uiso 1 1 calc R . .
C14 C 0.52795(19) 0.1491(3) 0.7935(10) 0.0242(11) Uani 1 1 d . . .
H14 H 0.5719 0.1429 0.8549 0.029 Uiso 1 1 calc R . .
C15 C 0.5000(2) 0.0901(3) 0.5962(11) 0.0251(9) Uani 1 1 d . . .
H15 H 0.5258 0.0454 0.5206 0.030 Uiso 1 1 calc R . .
C16 C 0.43594(19) 0.0972(2) 0.5140(9) 0.0201(8) Uani 1 1 d . . .
H16 H 0.4176 0.0562 0.3866 0.024 Uiso 1 1 calc R . .
C17 C 0.39652(18) 0.1648(2) 0.6159(8) 0.0143(7) Uani 1 1 d . . .
C18 C 0.32981(17) 0.1770(2) 0.5291(8) 0.0148(7) 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
Bi1 0.01521(6) 0.01590(6) 0.01339(6) -0.00315(12) 0.00014(13) -0.00113(5)
Cl1 0.0199(4) 0.0147(4) 0.0372(6) 0.0034(4) 0.0025(4) 0.0022(4)
O1 0.0148(10) 0.0193(11) 0.0144(11) -0.003(2) -0.0029(18) -0.0011(8)
C1 0.0164(18) 0.0176(19) 0.0131(18) -0.0039(16) 0.0010(15) -0.0065(15)
C2 0.0212(17) 0.0136(16) 0.018(3) -0.0054(17) -0.0037(17) -0.0019(13)
C3 0.029(2) 0.0205(19) 0.015(2) -0.0013(14) 0.0020(15) -0.0086(17)
C4 0.0179(15) 0.0237(17) 0.0189(16) -0.011(4) 0.006(3) -0.0050(13)
C5 0.0166(18) 0.026(2) 0.0155(19) -0.0023(17) -0.0030(15) -0.0003(16)
C6 0.0189(18) 0.018(2) 0.0119(17) -0.0055(15) -0.0032(15) -0.0037(16)
C7 0.0157(14) 0.0248(18) 0.019(2) 0.003(3) -0.001(2) 0.0016(13)
C8 0.0222(19) 0.0109(18) 0.019(2) -0.0003(15) -0.0020(16) -0.0013(15)
C9 0.0174(17) 0.0156(17) 0.0151(17) 0.0029(16) 0.0000(14) -0.0030(17)
C10 0.0213(16) 0.0129(15) 0.019(3) -0.0029(18) 0.0034(19) -0.0007(14)
C11 0.026(2) 0.019(2) 0.022(2) -0.0048(17) -0.0038(17) -0.0056(18)
C12 0.0202(17) 0.0195(19) 0.016(3) 0.0039(14) -0.0009(14) -0.0012(15)
C13 0.023(2) 0.024(2) 0.024(2) -0.0002(18) -0.0097(17) -0.0046(18)
C14 0.0200(17) 0.0276(19) 0.025(3) 0.0063(17) -0.0084(18) 0.0016(16)
C15 0.023(2) 0.018(2) 0.035(2) 0.0028(19) 0.0013(18) 0.0028(17)
C16 0.0184(19) 0.0163(19) 0.026(2) -0.0012(17) -0.0025(17) -0.0014(15)
C17 0.0173(18) 0.0115(17) 0.0141(16) 0.0037(15) 0.0010(14) -0.0037(15)
C18 0.0176(18) 0.0121(17) 0.0146(17) 0.0021(15) -0.0002(16) 0.0000(15)
_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
Bi1 C18 2.270(4) . ?
Bi1 C1 2.289(4) . ?
Bi1 O1 2.548(2) . ?
Bi1 Cl1 2.5803(10) . ?
O1 C7 1.446(4) . ?
O1 C8 1.460(6) . ?
C1 C6 1.394(5) . ?
C1 C2 1.402(6) . ?
C2 C3 1.406(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.507(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.498(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C18 1.375(5) . ?
C9 C10 1.422(6) . ?
C10 C11 1.358(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.412(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.431(5) . ?
C12 C17 1.432(5) . ?
C13 C14 1.355(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.418(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.372(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.421(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.438(5) . ?
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
C18 Bi1 C1 100.59(13) . . ?
C18 Bi1 O1 71.35(12) . . ?
C1 Bi1 O1 70.10(12) . . ?
C18 Bi1 Cl1 95.87(9) . . ?
C1 Bi1 Cl1 88.77(10) . . ?
O1 Bi1 Cl1 152.02(13) . . ?
C7 O1 C8 110.5(4) . . ?
C7 O1 Bi1 105.73(18) . . ?
C8 O1 Bi1 108.4(2) . . ?
C6 C1 C2 119.5(3) . . ?
C6 C1 Bi1 116.2(3) . . ?
C2 C1 Bi1 123.9(3) . . ?
C1 C2 C3 119.7(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 119.4(4) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 120.6(4) . . ?
C1 C6 C7 120.0(3) . . ?
C5 C6 C7 119.4(4) . . ?
O1 C7 C6 110.9(4) . . ?
O1 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
O1 C8 C9 110.6(3) . . ?
O1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C18 C9 C10 120.2(3) . . ?
C18 C9 C8 122.8(3) . . ?
C10 C9 C8 117.0(3) . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.3(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 121.8(4) . . ?
C11 C12 C17 120.1(3) . . ?
C13 C12 C17 118.2(4) . . ?
C14 C13 C12 121.9(4) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 119.7(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 121.3(4) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C12 118.4(3) . . ?
C16 C17 C18 123.6(3) . . ?
C12 C17 C18 117.9(3) . . ?
C9 C18 C17 120.2(3) . . ?
C9 C18 Bi1 117.2(3) . . ?
C17 C18 Bi1 122.5(3) . . ?
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
C18 Bi1 O1 C7 -143.8(4) . . . . ?
C1 Bi1 O1 C7 -34.7(4) . . . . ?
Cl1 Bi1 O1 C7 -77.8(4) . . . . ?
C18 Bi1 O1 C8 -25.3(2) . . . . ?
C1 Bi1 O1 C8 83.9(3) . . . . ?
Cl1 Bi1 O1 C8 40.8(3) . . . . ?
C18 Bi1 C1 C6 88.1(3) . . . . ?
O1 Bi1 C1 C6 22.5(3) . . . . ?
Cl1 Bi1 C1 C6 -176.2(3) . . . . ?
C18 Bi1 C1 C2 -99.2(3) . . . . ?
O1 Bi1 C1 C2 -164.7(4) . . . . ?
Cl1 Bi1 C1 C2 -3.4(3) . . . . ?
C6 C1 C2 C3 1.0(6) . . . . ?
Bi1 C1 C2 C3 -171.5(3) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 -1.1(7) . . . . ?
C2 C1 C6 C5 -1.8(6) . . . . ?
Bi1 C1 C6 C5 171.3(3) . . . . ?
C2 C1 C6 C7 179.1(4) . . . . ?
Bi1 C1 C6 C7 -7.8(5) . . . . ?
C4 C5 C6 C1 1.9(6) . . . . ?
C4 C5 C6 C7 -179.1(4) . . . . ?
C8 O1 C7 C6 -75.4(4) . . . . ?
Bi1 O1 C7 C6 41.7(5) . . . . ?
C1 C6 C7 O1 -26.5(6) . . . . ?
C5 C6 C7 O1 154.4(4) . . . . ?
C7 O1 C8 C9 148.0(3) . . . . ?
Bi1 O1 C8 C9 32.6(4) . . . . ?
O1 C8 C9 C18 -24.8(5) . . . . ?
O1 C8 C9 C10 156.9(4) . . . . ?
C18 C9 C10 C11 0.6(6) . . . . ?
C8 C9 C10 C11 178.9(4) . . . . ?
C9 C10 C11 C12 3.9(7) . . . . ?
C10 C11 C12 C13 176.0(4) . . . . ?
C10 C11 C12 C17 -3.0(6) . . . . ?
C11 C12 C13 C14 -174.1(4) . . . . ?
C17 C12 C13 C14 4.8(6) . . . . ?
C12 C13 C14 C15 -1.4(7) . . . . ?
C13 C14 C15 C16 -2.1(7) . . . . ?
C14 C15 C16 C17 2.0(7) . . . . ?
C15 C16 C17 C12 1.5(6) . . . . ?
C15 C16 C17 C18 177.8(4) . . . . ?
C11 C12 C17 C16 174.2(4) . . . . ?
C13 C12 C17 C16 -4.8(5) . . . . ?
C11 C12 C17 C18 -2.3(5) . . . . ?
C13 C12 C17 C18 178.7(3) . . . . ?
C10 C9 C18 C17 -6.0(5) . . . . ?
C8 C9 C18 C17 175.8(4) . . . . ?
C10 C9 C18 Bi1 178.5(3) . . . . ?
C8 C9 C18 Bi1 0.3(5) . . . . ?
C16 C17 C18 C9 -169.5(4) . . . . ?
C12 C17 C18 C9 6.7(5) . . . . ?
C16 C17 C18 Bi1 5.7(5) . . . . ?
C12 C17 C18 Bi1 -178.0(3) . . . . ?
C1 Bi1 C18 C9 -51.2(3) . . . . ?
O1 Bi1 C18 C9 13.4(3) . . . . ?
Cl1 Bi1 C18 C9 -141.0(3) . . . . ?
C1 Bi1 C18 C17 133.4(3) . . . . ?
O1 Bi1 C18 C17 -162.0(3) . . . . ?
Cl1 Bi1 C18 C17 43.6(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.089


data_cd212535
_database_code_depnum_ccdc_archive 'CCDC 909196'
#TrackingRef 'cd212535.cif'
_audit_update_record             
;
2013-02-25 # Formatted by publCIF
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Cl S Sb'
_chemical_formula_weight         419.55
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'
Cl Cl 0.1484 0.1585 '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)/n
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   11.4234(8)
_cell_length_b                   11.2183(8)
_cell_length_c                   13.3640(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.4280(10)
_cell_angle_gamma                90.00
_cell_volume                     1594.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5790
_cell_measurement_theta_min      4.890
_cell_measurement_theta_max      56.566
_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.132
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    2.019
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6168
_exptl_absorpt_correction_T_max  0.7765
_exptl_absorpt_process_details   sadabs
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9412
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3129
_reflns_number_gt                2859
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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^)+(0.0364P)^2^+0.4603P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3129
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0672
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.671616(15) 0.465385(14) 0.770745(13) 0.03808(8) Uani 1 1 d . . .
Cl1 Cl 0.67286(7) 0.68601(6) 0.80889(6) 0.05056(18) Uani 1 1 d . . .
S1 S 0.57491(7) 0.23855(6) 0.75504(6) 0.05006(18) Uani 1 1 d . . .
C1 C 0.4820(3) 0.4821(2) 0.6498(2) 0.0415(6) Uani 1 1 d . . .
C2 C 0.4246(3) 0.5926(3) 0.6185(2) 0.0490(7) Uani 1 1 d . . .
H2 H 0.4646 0.6607 0.6546 0.059 Uiso 1 1 calc R . .
C3 C 0.3100(3) 0.6035(3) 0.5356(3) 0.0605(8) Uani 1 1 d . . .
H3 H 0.2736 0.6782 0.5161 0.073 Uiso 1 1 calc R . .
C4 C 0.2498(3) 0.5033(4) 0.4816(3) 0.0699(10) Uani 1 1 d . . .
H4 H 0.1717 0.5099 0.4264 0.084 Uiso 1 1 calc R . .
C5 C 0.3057(3) 0.3927(3) 0.5099(3) 0.0669(9) Uani 1 1 d . . .
H5 H 0.2650 0.3251 0.4731 0.080 Uiso 1 1 calc R . .
C6 C 0.4212(3) 0.3814(3) 0.5921(2) 0.0497(7) Uani 1 1 d . . .
C7 C 0.4793(3) 0.2596(3) 0.6156(3) 0.0587(8) Uani 1 1 d . . .
H7A H 0.5306 0.2470 0.5726 0.070 Uiso 1 1 calc R . .
H7B H 0.4130 0.2002 0.5945 0.070 Uiso 1 1 calc R . .
C8 C 0.4731(3) 0.2871(3) 0.8244(2) 0.0512(7) Uani 1 1 d . . .
H8A H 0.4083 0.3400 0.7788 0.061 Uiso 1 1 calc R . .
H8B H 0.4328 0.2190 0.8430 0.061 Uiso 1 1 calc R . .
C9 C 0.5546(2) 0.3515(2) 0.9244(2) 0.0424(6) Uani 1 1 d . . .
C10 C 0.5361(3) 0.3290(3) 1.0216(3) 0.0554(7) Uani 1 1 d . . .
H10 H 0.4719 0.2781 1.0216 0.067 Uiso 1 1 calc R . .
C11 C 0.6102(3) 0.3802(3) 1.1140(3) 0.0616(8) Uani 1 1 d . . .
H11 H 0.5943 0.3666 1.1765 0.074 Uiso 1 1 calc R . .
C12 C 0.7110(3) 0.4536(3) 1.1177(2) 0.0523(7) Uani 1 1 d . . .
C13 C 0.7964(4) 0.5019(4) 1.2163(3) 0.0692(10) Uani 1 1 d . . .
H13 H 0.7817 0.4895 1.2795 0.083 Uiso 1 1 calc R . .
C14 C 0.8984(4) 0.5655(3) 1.2192(3) 0.0730(11) Uani 1 1 d . . .
H14 H 0.9519 0.5978 1.2838 0.088 Uiso 1 1 calc R . .
C15 C 0.9234(3) 0.5826(3) 1.1253(3) 0.0619(9) Uani 1 1 d . . .
H15 H 0.9961 0.6226 1.1285 0.074 Uiso 1 1 calc R . .
C16 C 0.8424(3) 0.5413(2) 1.0291(3) 0.0497(7) Uani 1 1 d . . .
H16 H 0.8595 0.5556 0.9673 0.060 Uiso 1 1 calc R . .
C17 C 0.7324(3) 0.4769(2) 1.0211(2) 0.0415(6) Uani 1 1 d . . .
C18 C 0.6475(3) 0.4284(2) 0.9225(2) 0.0393(6) 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
Sb1 0.03674(12) 0.03725(12) 0.03929(12) -0.00130(7) 0.01275(9) -0.00303(6)
Cl1 0.0540(4) 0.0370(3) 0.0535(4) -0.0002(3) 0.0111(3) -0.0092(3)
S1 0.0530(4) 0.0357(3) 0.0576(4) -0.0034(3) 0.0156(3) -0.0014(3)
C1 0.0419(15) 0.0439(14) 0.0356(14) 0.0000(11) 0.0106(12) -0.0035(12)
C2 0.0543(17) 0.0460(15) 0.0423(15) 0.0057(13) 0.0125(13) -0.0028(13)
C3 0.0568(19) 0.0647(19) 0.0480(17) 0.0180(15) 0.0050(14) 0.0069(16)
C4 0.0509(19) 0.092(2) 0.0466(19) 0.0090(19) -0.0060(15) -0.0020(19)
C5 0.064(2) 0.073(2) 0.0469(18) -0.0075(16) 0.0002(15) -0.0173(18)
C6 0.0511(16) 0.0532(16) 0.0392(15) -0.0070(13) 0.0099(12) -0.0105(14)
C7 0.067(2) 0.0449(15) 0.0535(18) -0.0165(14) 0.0092(15) -0.0094(15)
C8 0.0476(16) 0.0467(15) 0.0591(18) 0.0027(14) 0.0193(14) -0.0085(13)
C9 0.0396(14) 0.0369(13) 0.0506(15) 0.0064(12) 0.0162(12) 0.0064(11)
C10 0.0541(16) 0.0558(17) 0.0644(19) 0.0115(15) 0.0313(15) 0.0041(14)
C11 0.071(2) 0.070(2) 0.0529(19) 0.0106(16) 0.0343(17) 0.0141(18)
C12 0.0575(19) 0.0524(16) 0.0423(16) 0.0024(12) 0.0127(14) 0.0202(14)
C13 0.084(3) 0.072(2) 0.0421(19) -0.0021(17) 0.0125(17) 0.024(2)
C14 0.079(3) 0.065(2) 0.047(2) -0.0095(17) -0.0096(18) 0.018(2)
C15 0.0564(19) 0.0432(16) 0.064(2) -0.0053(15) -0.0035(16) 0.0045(14)
C16 0.0508(17) 0.0373(14) 0.0499(17) 0.0024(12) 0.0053(14) 0.0056(12)
C17 0.0418(14) 0.0358(13) 0.0418(15) 0.0020(11) 0.0093(12) 0.0110(11)
C18 0.0420(14) 0.0338(12) 0.0412(14) 0.0042(11) 0.0140(11) 0.0049(11)
_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 C18 2.184(3) . ?
Sb1 C1 2.186(3) . ?
Sb1 Cl1 2.5260(7) . ?
Sb1 S1 2.7515(7) . ?
S1 C7 1.799(3) . ?
S1 C8 1.815(3) . ?
C1 C2 1.393(4) . ?
C1 C6 1.401(4) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.501(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.505(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C18 1.375(4) . ?
C9 C10 1.411(4) . ?
C10 C11 1.344(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.402(5) . ?
C11 H11 0.9300 . ?
C12 C17 1.423(4) . ?
C12 C13 1.430(5) . ?
C13 C14 1.355(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.399(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.362(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.419(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.428(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
C18 Sb1 C1 106.01(10) . . ?
C18 Sb1 Cl1 89.55(7) . . ?
C1 Sb1 Cl1 89.78(7) . . ?
C18 Sb1 S1 73.24(7) . . ?
C1 Sb1 S1 76.19(7) . . ?
Cl1 Sb1 S1 153.39(2) . . ?
C7 S1 C8 103.28(15) . . ?
C7 S1 Sb1 91.87(10) . . ?
C8 S1 Sb1 89.86(9) . . ?
C2 C1 C6 117.9(3) . . ?
C2 C1 Sb1 121.9(2) . . ?
C6 C1 Sb1 119.7(2) . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 C7 118.1(3) . . ?
C1 C6 C7 121.8(3) . . ?
C6 C7 S1 113.0(2) . . ?
C6 C7 H7A 109.0 . . ?
S1 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
S1 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C9 C8 S1 107.09(19) . . ?
C9 C8 H8A 110.3 . . ?
S1 C8 H8A 110.3 . . ?
C9 C8 H8B 110.3 . . ?
S1 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
C18 C9 C10 120.3(3) . . ?
C18 C9 C8 121.0(2) . . ?
C10 C9 C8 118.7(3) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 121.1(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C17 119.2(3) . . ?
C11 C12 C13 122.0(3) . . ?
C17 C12 C13 118.8(3) . . ?
C14 C13 C12 121.1(4) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.6(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 121.5(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C12 117.8(3) . . ?
C16 C17 C18 123.2(3) . . ?
C12 C17 C18 118.9(3) . . ?
C9 C18 C17 119.4(2) . . ?
C9 C18 Sb1 119.8(2) . . ?
C17 C18 Sb1 120.7(2) . . ?
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
C18 Sb1 S1 C7 142.74(14) . . . . ?
C1 Sb1 S1 C7 30.99(14) . . . . ?
Cl1 Sb1 S1 C7 91.02(13) . . . . ?
C18 Sb1 S1 C8 39.45(12) . . . . ?
C1 Sb1 S1 C8 -72.30(13) . . . . ?
Cl1 Sb1 S1 C8 -12.27(12) . . . . ?
C18 Sb1 C1 C2 96.8(2) . . . . ?
Cl1 Sb1 C1 C2 7.3(2) . . . . ?
S1 Sb1 C1 C2 164.5(2) . . . . ?
C18 Sb1 C1 C6 -91.1(2) . . . . ?
Cl1 Sb1 C1 C6 179.5(2) . . . . ?
S1 Sb1 C1 C6 -23.4(2) . . . . ?
C6 C1 C2 C3 1.7(4) . . . . ?
Sb1 C1 C2 C3 174.0(2) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C1 1.5(5) . . . . ?
C4 C5 C6 C7 -177.4(3) . . . . ?
C2 C1 C6 C5 -2.5(4) . . . . ?
Sb1 C1 C6 C5 -175.0(2) . . . . ?
C2 C1 C6 C7 176.4(3) . . . . ?
Sb1 C1 C6 C7 3.9(4) . . . . ?
C5 C6 C7 S1 -148.8(3) . . . . ?
C1 C6 C7 S1 32.3(4) . . . . ?
C8 S1 C7 C6 50.2(3) . . . . ?
Sb1 S1 C7 C6 -40.1(2) . . . . ?
C7 S1 C8 C9 -142.14(19) . . . . ?
Sb1 S1 C8 C9 -50.25(18) . . . . ?
S1 C8 C9 C18 41.3(3) . . . . ?
S1 C8 C9 C10 -137.0(2) . . . . ?
C18 C9 C10 C11 -1.3(4) . . . . ?
C8 C9 C10 C11 177.0(3) . . . . ?
C9 C10 C11 C12 -2.6(5) . . . . ?
C10 C11 C12 C17 1.9(4) . . . . ?
C10 C11 C12 C13 -175.4(3) . . . . ?
C11 C12 C13 C14 175.2(3) . . . . ?
C17 C12 C13 C14 -2.2(5) . . . . ?
C12 C13 C14 C15 -1.5(6) . . . . ?
C13 C14 C15 C16 3.5(5) . . . . ?
C14 C15 C16 C17 -1.8(4) . . . . ?
C15 C16 C17 C12 -1.8(4) . . . . ?
C15 C16 C17 C18 -177.7(3) . . . . ?
C11 C12 C17 C16 -173.7(3) . . . . ?
C13 C12 C17 C16 3.7(4) . . . . ?
C11 C12 C17 C18 2.4(4) . . . . ?
C13 C12 C17 C18 179.8(3) . . . . ?
C10 C9 C18 C17 5.7(4) . . . . ?
C8 C9 C18 C17 -172.6(2) . . . . ?
C10 C9 C18 Sb1 -178.5(2) . . . . ?
C8 C9 C18 Sb1 3.2(3) . . . . ?
C16 C17 C18 C9 169.7(2) . . . . ?
C12 C17 C18 C9 -6.2(4) . . . . ?
C16 C17 C18 Sb1 -6.0(3) . . . . ?
C12 C17 C18 Sb1 178.07(18) . . . . ?
C1 Sb1 C18 C9 40.7(2) . . . . ?
Cl1 Sb1 C18 C9 130.4(2) . . . . ?
S1 Sb1 C18 C9 -29.03(18) . . . . ?
C1 Sb1 C18 C17 -143.5(2) . . . . ?
Cl1 Sb1 C18 C17 -53.86(19) . . . . ?
S1 Sb1 C18 C17 146.7(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.009
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.075


data_cd212520
_database_code_depnum_ccdc_archive 'CCDC 909197'
#TrackingRef 'cif 3.cif'
_audit_update_record             
;
2012-11-05 # Formatted by publCIF
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Bi Cl S'
_chemical_formula_weight         506.78
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 '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)/n
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   11.6940(12)
_cell_length_b                   11.4596(12)
_cell_length_c                   12.4340(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.526(2)
_cell_angle_gamma                90.00
_cell_volume                     1560.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4332
_cell_measurement_theta_min      4.987
_cell_measurement_theta_max      56.187
_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.112
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    11.593
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.06827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9015
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_sigmaI/netI    0.0775
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3063
_reflns_number_gt                2598
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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^)+(0.0595P)^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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3063
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
Bi1 Bi 0.13042(2) 0.03405(3) 0.70665(2) 0.03101(16) Uani 1 1 d . . .
Cl1 Cl 0.16137(17) -0.19310(19) 0.74904(18) 0.0505(5) Uani 1 1 d . . .
S1 S 0.0132(2) 0.25153(18) 0.69214(19) 0.0478(5) Uani 1 1 d . . .
C1 C -0.0737(6) -0.0004(7) 0.6117(6) 0.0302(16) Uani 1 1 d . . .
C2 C -0.1184(6) -0.1148(7) 0.5973(6) 0.0333(17) Uani 1 1 d . . .
H2 H -0.0657 -0.1761 0.6302 0.040 Uiso 1 1 calc R . .
C3 C -0.2388(7) -0.1382(8) 0.5354(7) 0.044(2) Uani 1 1 d . . .
H3 H -0.2670 -0.2148 0.5252 0.053 Uiso 1 1 calc R . .
C4 C -0.3179(8) -0.0464(9) 0.4883(8) 0.053(2) Uani 1 1 d . . .
H4 H -0.4002 -0.0613 0.4490 0.064 Uiso 1 1 calc R . .
C5 C -0.2752(8) 0.0666(10) 0.4993(8) 0.053(2) Uani 1 1 d . . .
H5 H -0.3284 0.1277 0.4665 0.064 Uiso 1 1 calc R . .
C6 C -0.1525(7) 0.0890(7) 0.5596(6) 0.0361(17) Uani 1 1 d . . .
C7 C -0.1098(8) 0.2140(7) 0.5636(7) 0.051(2) Uani 1 1 d . . .
H7A H -0.1782 0.2654 0.5558 0.061 Uiso 1 1 calc R . .
H7B H -0.0842 0.2277 0.4984 0.061 Uiso 1 1 calc R . .
C8 C -0.0500(7) 0.2078(7) 0.8003(6) 0.0424(19) Uani 1 1 d . . .
H8A H -0.0792 0.2764 0.8283 0.051 Uiso 1 1 calc R . .
H8B H -0.1192 0.1566 0.7655 0.051 Uiso 1 1 calc R . .
C9 C 0.0425(6) 0.1460(7) 0.8998(7) 0.0363(17) Uani 1 1 d . . .
C10 C 0.0369(7) 0.1633(8) 1.0100(7) 0.048(2) Uani 1 1 d . . .
H10 H -0.0231 0.2123 1.0177 0.057 Uiso 1 1 calc R . .
C11 C 0.1140(8) 0.1124(9) 1.1034(8) 0.054(2) Uani 1 1 d . . .
H11 H 0.1056 0.1238 1.1743 0.065 Uiso 1 1 calc R . .
C12 C 0.2095(8) 0.0404(7) 1.0945(7) 0.042(2) Uani 1 1 d . . .
C13 C 0.2983(9) -0.0107(8) 1.1940(7) 0.050(2) Uani 1 1 d . . .
H13 H 0.2894 -0.0044 1.2652 0.059 Uiso 1 1 calc R . .
C14 C 0.3956(9) -0.0684(9) 1.1840(9) 0.064(3) Uani 1 1 d . . .
H14 H 0.4540 -0.1006 1.2487 0.077 Uiso 1 1 calc R . .
C15 C 0.4083(7) -0.0793(8) 1.0780(8) 0.048(2) Uani 1 1 d . . .
H15 H 0.4775 -0.1154 1.0731 0.058 Uiso 1 1 calc R . .
C16 C 0.3227(7) -0.0391(6) 0.9821(7) 0.0364(19) Uani 1 1 d . . .
H16 H 0.3320 -0.0517 0.9118 0.044 Uiso 1 1 calc R . .
C17 C 0.2184(7) 0.0224(6) 0.9850(6) 0.0308(17) Uani 1 1 d . . .
C18 C 0.1302(6) 0.0716(7) 0.8876(6) 0.0336(17) 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
Bi1 0.0316(2) 0.0264(2) 0.0364(2) -0.00200(11) 0.01363(14) 0.00121(11)
Cl1 0.0453(10) 0.0317(11) 0.0558(11) -0.0027(10) -0.0058(9) 0.0082(9)
S1 0.0585(12) 0.0206(10) 0.0671(13) 0.0024(10) 0.0256(10) 0.0021(10)
C1 0.025(3) 0.034(4) 0.028(4) -0.008(3) 0.006(3) -0.002(3)
C2 0.031(3) 0.034(5) 0.033(4) 0.000(3) 0.009(3) -0.001(3)
C3 0.044(4) 0.039(5) 0.045(4) -0.006(4) 0.011(3) -0.008(4)
C4 0.037(4) 0.061(7) 0.048(5) -0.010(5) 0.000(4) 0.010(4)
C5 0.045(5) 0.065(7) 0.042(5) 0.005(5) 0.004(4) 0.025(5)
C6 0.043(4) 0.030(4) 0.035(4) 0.004(3) 0.014(3) 0.013(4)
C7 0.077(6) 0.028(5) 0.047(4) 0.011(4) 0.020(4) 0.016(5)
C8 0.047(4) 0.034(5) 0.047(4) -0.007(4) 0.019(3) 0.009(4)
C9 0.036(4) 0.027(4) 0.050(4) -0.013(4) 0.019(3) -0.007(3)
C10 0.045(4) 0.042(5) 0.062(5) -0.013(5) 0.026(4) -0.007(4)
C11 0.064(5) 0.058(6) 0.048(5) -0.020(5) 0.029(4) -0.019(5)
C12 0.046(5) 0.038(5) 0.040(4) -0.010(4) 0.015(4) -0.021(4)
C13 0.071(6) 0.038(5) 0.036(5) 0.006(4) 0.015(4) -0.023(5)
C14 0.071(7) 0.044(6) 0.050(6) 0.006(5) -0.013(5) -0.017(5)
C15 0.044(4) 0.031(5) 0.053(5) 0.004(4) -0.004(4) 0.007(4)
C16 0.041(4) 0.022(4) 0.038(4) -0.007(3) 0.004(3) -0.009(3)
C17 0.036(4) 0.022(4) 0.032(4) -0.005(3) 0.009(3) -0.015(3)
C18 0.039(4) 0.021(4) 0.042(4) -0.007(3) 0.016(3) -0.010(3)
_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
Bi1 C18 2.292(7) . ?
Bi1 C1 2.296(7) . ?
Bi1 Cl1 2.655(2) . ?
Bi1 S1 2.819(2) . ?
S1 C7 1.788(9) . ?
S1 C8 1.817(8) . ?
C1 C6 1.379(11) . ?
C1 C2 1.400(11) . ?
C2 C3 1.373(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.512(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.505(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C18 1.382(10) . ?
C9 C10 1.408(10) . ?
C10 C11 1.330(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.424(12) . ?
C11 H11 0.9300 . ?
C12 C17 1.415(12) . ?
C12 C13 1.433(13) . ?
C13 C14 1.358(15) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(15) . ?
C14 H14 0.9300 . ?
C15 C16 1.341(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.421(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.404(11) . ?
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
C18 Bi1 C1 100.3(3) . . ?
C18 Bi1 Cl1 92.1(2) . . ?
C1 Bi1 Cl1 88.7(2) . . ?
C18 Bi1 S1 74.3(2) . . ?
C1 Bi1 S1 74.0(2) . . ?
Cl1 Bi1 S1 155.32(7) . . ?
C7 S1 C8 100.7(4) . . ?
C7 S1 Bi1 93.7(3) . . ?
C8 S1 Bi1 91.4(3) . . ?
C6 C1 C2 118.5(7) . . ?
C6 C1 Bi1 121.1(6) . . ?
C2 C1 Bi1 120.1(5) . . ?
C3 C2 C1 121.2(7) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.3(9) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 120.4(8) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.8(8) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.7(8) . . ?
C1 C6 C7 122.0(7) . . ?
C5 C6 C7 117.3(8) . . ?
C6 C7 S1 114.2(5) . . ?
C6 C7 H7A 108.7 . . ?
S1 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
S1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 S1 112.1(5) . . ?
C9 C8 H8A 109.2 . . ?
S1 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
S1 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C18 C9 C10 118.8(8) . . ?
C18 C9 C8 123.2(7) . . ?
C10 C9 C8 117.9(7) . . ?
C11 C10 C9 122.7(8) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C10 C11 C12 119.7(8) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C17 C12 C11 118.9(8) . . ?
C17 C12 C13 119.7(8) . . ?
C11 C12 C13 121.3(8) . . ?
C14 C13 C12 119.8(9) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.3(9) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 121.3(9) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 121.9(8) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C12 119.4(7) . . ?
C18 C17 C16 123.7(7) . . ?
C12 C17 C16 116.7(7) . . ?
C9 C18 C17 120.1(7) . . ?
C9 C18 Bi1 118.6(5) . . ?
C17 C18 Bi1 121.2(5) . . ?
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
C18 Bi1 S1 C7 -133.6(4) . . . . ?
C1 Bi1 S1 C7 -27.8(4) . . . . ?
Cl1 Bi1 S1 C7 -75.1(3) . . . . ?
C18 Bi1 S1 C8 -32.8(3) . . . . ?
C1 Bi1 S1 C8 73.1(3) . . . . ?
Cl1 Bi1 S1 C8 25.7(3) . . . . ?
C18 Bi1 C1 C6 89.9(6) . . . . ?
Cl1 Bi1 C1 C6 -178.2(6) . . . . ?
S1 Bi1 C1 C6 19.7(5) . . . . ?
C18 Bi1 C1 C2 -95.6(6) . . . . ?
Cl1 Bi1 C1 C2 -3.7(5) . . . . ?
S1 Bi1 C1 C2 -165.8(6) . . . . ?
C6 C1 C2 C3 -1.7(11) . . . . ?
Bi1 C1 C2 C3 -176.4(6) . . . . ?
C1 C2 C3 C4 -1.3(12) . . . . ?
C2 C3 C4 C5 2.7(13) . . . . ?
C3 C4 C5 C6 -1.0(14) . . . . ?
C2 C1 C6 C5 3.4(11) . . . . ?
Bi1 C1 C6 C5 178.0(6) . . . . ?
C2 C1 C6 C7 -175.6(7) . . . . ?
Bi1 C1 C6 C7 -1.0(10) . . . . ?
C4 C5 C6 C1 -2.1(13) . . . . ?
C4 C5 C6 C7 177.0(8) . . . . ?
C1 C6 C7 S1 -32.1(10) . . . . ?
C5 C6 C7 S1 148.8(7) . . . . ?
C8 S1 C7 C6 -53.9(7) . . . . ?
Bi1 S1 C7 C6 38.2(6) . . . . ?
C7 S1 C8 C9 137.7(6) . . . . ?
Bi1 S1 C8 C9 43.6(6) . . . . ?
S1 C8 C9 C18 -36.0(10) . . . . ?
S1 C8 C9 C10 145.5(6) . . . . ?
C18 C9 C10 C11 1.2(13) . . . . ?
C8 C9 C10 C11 179.7(8) . . . . ?
C9 C10 C11 C12 2.3(14) . . . . ?
C10 C11 C12 C17 -1.5(12) . . . . ?
C10 C11 C12 C13 176.6(8) . . . . ?
C17 C12 C13 C14 5.1(13) . . . . ?
C11 C12 C13 C14 -172.9(8) . . . . ?
C12 C13 C14 C15 -1.0(14) . . . . ?
C13 C14 C15 C16 -3.4(15) . . . . ?
C14 C15 C16 C17 3.5(13) . . . . ?
C11 C12 C17 C18 -2.7(11) . . . . ?
C13 C12 C17 C18 179.2(7) . . . . ?
C11 C12 C17 C16 173.2(7) . . . . ?
C13 C12 C17 C16 -4.9(10) . . . . ?
C15 C16 C17 C18 176.4(8) . . . . ?
C15 C16 C17 C12 0.7(11) . . . . ?
C10 C9 C18 C17 -5.4(11) . . . . ?
C8 C9 C18 C17 176.1(7) . . . . ?
C10 C9 C18 Bi1 175.9(6) . . . . ?
C8 C9 C18 Bi1 -2.6(10) . . . . ?
C12 C17 C18 C9 6.2(11) . . . . ?
C16 C17 C18 C9 -169.4(7) . . . . ?
C12 C17 C18 Bi1 -175.2(5) . . . . ?
C16 C17 C18 Bi1 9.3(10) . . . . ?
C1 Bi1 C18 C9 -45.9(6) . . . . ?
Cl1 Bi1 C18 C9 -135.0(6) . . . . ?
S1 Bi1 C18 C9 24.1(5) . . . . ?
C1 Bi1 C18 C17 135.4(6) . . . . ?
Cl1 Bi1 C18 C17 46.3(6) . . . . ?
S1 Bi1 C18 C17 -154.6(6) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.790
_refine_diff_density_min         -2.783
_refine_diff_density_rms         0.265