# 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H21 Cl2 N2 Sb'
_chemical_formula_sum            'C17 H21 Cl2 N2 Sb'
_chemical_formula_weight         446.01

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'
N N 0.0061 0.0033 '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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.1671(7)
_cell_length_b                   10.8550(5)
_cell_length_c                   17.3739(7)
_cell_angle_alpha                90
_cell_angle_beta                 119.731(4)
_cell_angle_gamma                90
_cell_volume                     1828.81(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    23756
_cell_measurement_theta_min      1
_cell_measurement_theta_max      30.5

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    1.799
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.115
-1 0 -1 0.045
-1 0 1 0.109
1 0 -1 0.119
0 -1 0 0.096
0 1 0 0.089
0 -1 -1 0.110
1 0 0 0.113


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_T_max  0.778
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_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  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23704
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         30.50
_reflns_number_total             5544
_reflns_number_gt                4835
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0138P)²+1.8064P] 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         5544
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0574
_refine_ls_wR_factor_gt          0.0504
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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 0.039813(11) 0.174297(11) 0.563785(7) 0.01850(4) Uani 1 1 d . . .
Cl2 Cl -0.15769(5) 0.01961(5) 0.51654(3) 0.02698(10) Uani 1 1 d . . .
Cl1 Cl -0.03120(5) 0.28799(5) 0.65059(3) 0.02725(9) Uani 1 1 d . . .
N2 N 0.25322(15) 0.26950(14) 0.64437(10) 0.0181(3) Uani 1 1 d . . .
C6 C 0.27801(17) 0.39169(16) 0.62535(12) 0.0180(3) Uani 1 1 d . . .
C16 C 0.4166(3) 0.2971(2) 0.49085(18) 0.0397(5) Uani 1 1 d . . .
H16A H 0.4297 0.3701 0.4647 0.048 Uiso 1 1 d R . .
H16B H 0.4176 0.2261 0.4582 0.048 Uiso 1 1 d R . .
H16C H 0.4895 0.2905 0.5512 0.048 Uiso 1 1 d R . .
N1 N 0.15889(15) 0.05782(14) 0.66981(10) 0.0190(3) Uani 1 1 d . . .
C13 C 0.4390(3) 0.4990(3) 0.84572(17) 0.0581(9) Uani 1 1 d . . .
H13A H 0.4606 0.5836 0.8421 0.070 Uiso 1 1 d R . .
H13B H 0.5049 0.4467 0.8416 0.070 Uiso 1 1 d R . .
H13C H 0.4423 0.4849 0.9013 0.070 Uiso 1 1 d R . .
C7 C 0.28854(19) 0.48936(17) 0.68127(13) 0.0218(3) Uani 1 1 d . . .
C4 C 0.1366(2) -0.05224(17) 0.69784(13) 0.0239(4) Uani 1 1 d . . .
H4 H 0.0535 -0.0949 0.6713 0.029 Uiso 1 1 d R . .
C5 C 0.34049(18) 0.20458(17) 0.71122(12) 0.0195(3) Uani 1 1 d . . .
H5 H 0.4302 0.2319 0.7480 0.023 Uiso 1 1 d R . .
C12 C 0.2941(2) 0.4708(2) 0.76959(15) 0.0312(4) Uani 1 1 d . . .
H12 H 0.2750 0.3838 0.7741 0.037 Uiso 1 1 d R . .
C11 C 0.27872(19) 0.41086(17) 0.54529(12) 0.0211(3) Uani 1 1 d . . .
C8 C 0.2960(2) 0.60865(18) 0.65338(15) 0.0263(4) Uani 1 1 d . . .
H8 H 0.3031 0.6753 0.6891 0.032 Uiso 1 1 d R . .
C15 C 0.2780(2) 0.30466(19) 0.48854(13) 0.0283(4) Uani 1 1 d . . .
H15 H 0.2660 0.2283 0.5141 0.034 Uiso 1 1 d R . .
C9 C 0.2937(2) 0.62984(19) 0.57450(14) 0.0283(4) Uani 1 1 d . . .
H9 H 0.2966 0.7102 0.5568 0.034 Uiso 1 1 d R . .
C1 C 0.29509(18) 0.09005(17) 0.72625(12) 0.0191(3) Uani 1 1 d . . .
C2 C 0.35766(19) -0.00133(17) 0.79002(13) 0.0229(4) Uani 1 1 d . . .
H2 H 0.4488 -0.0029 0.8357 0.028 Uiso 1 1 d R . .
C10 C 0.2863(2) 0.53184(19) 0.52134(13) 0.0268(4) Uani 1 1 d . . .
H10 H 0.2868 0.5472 0.4688 0.032 Uiso 1 1 d R . .
C3 C 0.2568(2) -0.09070(18) 0.77197(14) 0.0258(4) Uani 1 1 d . . .
H3 H 0.2682 -0.1627 0.8039 0.031 Uiso 1 1 d R . .
C17 C 0.1593(3) 0.3137(3) 0.39306(16) 0.0438(6) Uani 1 1 d . . .
H17A H 0.0736 0.3194 0.3932 0.053 Uiso 1 1 d R . .
H17B H 0.1582 0.2417 0.3606 0.053 Uiso 1 1 d R . .
H17C H 0.1711 0.3857 0.3655 0.053 Uiso 1 1 d R . .
C14 C 0.1848(4) 0.5476(2) 0.7760(2) 0.0560(8) Uani 1 1 d . . .
H14A H 0.1892 0.5323 0.8318 0.067 Uiso 1 1 d R . .
H14B H 0.0951 0.5254 0.7286 0.067 Uiso 1 1 d R . .
H14C H 0.2012 0.6334 0.7716 0.067 Uiso 1 1 d R . .


_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 N1 2.0810(15) . ?
Sb1 N2 2.3234(15) . ?
Sb1 Cl1 2.3691(5) . ?
Sb1 Cl2 2.5616(5) . ?
N2 C5 1.293(2) . ?
N2 C6 1.427(2) . ?
C6 C7 1.403(3) . ?
C6 C11 1.410(2) . ?
C16 C15 1.531(3) . ?
C16 H16A 0.9599 . ?
C16 H16B 0.9601 . ?
C16 H16C 0.9599 . ?
N1 C4 1.359(2) . ?
N1 C1 1.385(2) . ?
C13 C12 1.529(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9599 . ?
C7 C8 1.400(3) . ?
C7 C12 1.518(3) . ?
C4 C3 1.386(3) . ?
C4 H4 0.9299 . ?
C5 C1 1.415(2) . ?
C5 H5 0.9300 . ?
C12 C14 1.527(4) . ?
C12 H12 0.9799 . ?
C11 C10 1.393(3) . ?
C11 C15 1.514(3) . ?
C8 C9 1.377(3) . ?
C8 H8 0.9300 . ?
C15 C17 1.529(3) . ?
C15 H15 0.9800 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9300 . ?
C1 C2 1.390(3) . ?
C2 C3 1.399(3) . ?
C2 H2 0.9300 . ?
C10 H10 0.9300 . ?
C3 H3 0.9299 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9601 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Sb1 N2 73.90(6) . . ?
N1 Sb1 Cl1 91.24(4) . . ?
N2 Sb1 Cl1 87.24(4) . . ?
N1 Sb1 Cl2 87.48(4) . . ?
N2 Sb1 Cl2 161.35(4) . . ?
Cl1 Sb1 Cl2 92.213(17) . . ?
C5 N2 C6 124.62(15) . . ?
C5 N2 Sb1 112.93(12) . . ?
C6 N2 Sb1 122.19(11) . . ?
C7 C6 C11 122.14(16) . . ?
C7 C6 N2 120.08(16) . . ?
C11 C6 N2 117.54(16) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.4 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 N1 C1 107.48(15) . . ?
C4 N1 Sb1 134.53(13) . . ?
C1 N1 Sb1 117.94(12) . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C7 C6 117.27(17) . . ?
C8 C7 C12 119.55(18) . . ?
C6 C7 C12 123.17(17) . . ?
N1 C4 C3 109.44(17) . . ?
N1 C4 H4 125.1 . . ?
C3 C4 H4 125.4 . . ?
N2 C5 C1 117.72(16) . . ?
N2 C5 H5 121.2 . . ?
C1 C5 H5 121.1 . . ?
C7 C12 C14 111.6(2) . . ?
C7 C12 C13 110.08(18) . . ?
C14 C12 C13 111.6(2) . . ?
C7 C12 H12 107.9 . . ?
C14 C12 H12 107.9 . . ?
C13 C12 H12 107.6 . . ?
C10 C11 C6 117.69(17) . . ?
C10 C11 C15 120.32(17) . . ?
C6 C11 C15 121.93(16) . . ?
C9 C8 C7 121.62(19) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C11 C15 C17 112.3(2) . . ?
C11 C15 C16 110.16(17) . . ?
C17 C15 C16 110.67(19) . . ?
C11 C15 H15 107.9 . . ?
C17 C15 H15 107.8 . . ?
C16 C15 H15 107.8 . . ?
C8 C9 C10 120.07(19) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 120.1 . . ?
N1 C1 C2 108.99(16) . . ?
N1 C1 C5 117.36(16) . . ?
C2 C1 C5 133.61(17) . . ?
C1 C2 C3 106.60(17) . . ?
C1 C2 H2 126.7 . . ?
C3 C2 H2 126.7 . . ?
C9 C10 C11 121.18(19) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.5 . . ?
C4 C3 C2 107.48(17) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.3 . . ?
C15 C17 H17A 109.2 . . ?
C15 C17 H17B 109.7 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C14 H14A 109.7 . . ?
C12 C14 H14B 109.3 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.4 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.100
_database_code_depnum_ccdc_archive 'CCDC 1017116'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H22 Cl2 N3 Sb), C H2 Cl2'
_chemical_formula_sum            'C29 H46 Cl6 N6 Sb2'
_chemical_formula_weight         934.92

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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   'C 2'
_symmetry_space_group_name_Hall  'C 2y'

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

_cell_length_a                   19.8552(4)
_cell_length_b                   8.2449(3)
_cell_length_c                   14.0093(6)
_cell_angle_alpha                90
_cell_angle_beta                 130.412(4)
_cell_angle_gamma                90
_cell_volume                     1746.19(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    6538
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             932
_exptl_absorpt_coefficient_mu    2.037
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.097
1 0 -1 0.091
0 1 0 0.127
0 -1 0 0.144
-1 0 0 0.119
1 0 0 0.098
-1 -1 1 0.145
1 -1 -1 0.127
1 1 -1 0.136
-1 -1 0 0.133


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_T_max  0.706
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_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  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6524
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3739
_reflns_number_gt                3682
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0154P)²+1.3047P] 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   -0.034(13)
_refine_ls_number_reflns         3739
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0172
_refine_ls_R_factor_gt           0.0162
_refine_ls_wR_factor_ref         0.0427
_refine_ls_wR_factor_gt          0.0419
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.146
_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
Sb1 Sb 0.014231(8) 0.01959(2) 0.355435(11) 0.01283(4) Uani 1 1 d . . .
Cl1 Cl -0.06706(5) 0.24805(8) 0.18899(7) 0.02443(16) Uani 1 1 d . . .
Cl2 Cl 0.10631(4) -0.21376(7) 0.50847(6) 0.02123(12) Uani 1 1 d . . .
N1 N 0.07916(13) -0.0227(2) 0.29106(18) 0.0163(4) Uani 1 1 d . . .
C2 C 0.15084(14) 0.0306(4) 0.2226(2) 0.0207(4) Uani 1 1 d . . .
H2 H 0.1872 0.0789 0.2107 0.025 Uiso 1 1 d R . .
C6 C 0.12106(17) 0.3652(3) 0.4946(2) 0.0214(5) Uani 1 1 d . . .
H6A H 0.0608 0.4009 0.4279 0.026 Uiso 1 1 d R . .
H6B H 0.1614 0.4493 0.5105 0.026 Uiso 1 1 d R . .
C7 C 0.13488(18) 0.3267(3) 0.6121(3) 0.0254(5) Uani 1 1 d . . .
H7A H 0.0789 0.3056 0.5921 0.030 Uiso 1 1 d R . .
H7B H 0.1639 0.4165 0.6707 0.030 Uiso 1 1 d R . .
C8 C 0.19409(17) 0.1744(3) 0.6679(2) 0.0240(5) Uani 1 1 d . . .
H8A H 0.2471 0.1935 0.7540 0.029 Uiso 1 1 d R . .
H8B H 0.1625 0.0827 0.6659 0.029 Uiso 1 1 d R . .
C1 C 0.13536(15) 0.0837(3) 0.2997(2) 0.0173(5) Uani 1 1 d . . .
Cl3 Cl 0.09607(5) 0.44001(9) 0.09687(6) 0.03116(15) Uani 1 1 d . . .
N2 N 0.13883(13) 0.2093(2) 0.46055(18) 0.0166(4) Uani 1 1 d . . .
C9 C 0.21715(15) 0.1443(3) 0.5848(2) 0.0201(5) Uani 1 1 d . . .
H9A H 0.2708 0.2010 0.6161 0.024 Uiso 1 1 d R . .
H9B H 0.2247 0.0293 0.5795 0.024 Uiso 1 1 d R . .
C12 C -0.21278(16) -0.0963(3) 0.0825(2) 0.0234(5) Uani 1 1 d . . .
H12A H -0.2716 -0.0957 0.0009 0.028 Uiso 1 1 d R . .
H12B H -0.2022 0.0068 0.1236 0.028 Uiso 1 1 d R . .
C10 C -0.00042(15) -0.2736(3) 0.1955(2) 0.0193(5) Uani 1 1 d . . .
H10A H 0.0345 -0.3503 0.2642 0.023 Uiso 1 1 d R . .
H10B H -0.0296 -0.3319 0.1175 0.023 Uiso 1 1 d R . .
C13 C -0.20145(16) -0.2383(4) 0.1628(2) 0.0252(5) Uani 1 1 d . . .
H13A H -0.2041 -0.2003 0.2258 0.030 Uiso 1 1 d R . .
H13B H -0.2475 -0.3187 0.1109 0.030 Uiso 1 1 d R . .
C11 C -0.14339(16) -0.1290(3) 0.0707(2) 0.0207(5) Uani 1 1 d . . .
H11A H -0.1643 -0.2081 0.0055 0.025 Uiso 1 1 d R . .
H11B H -0.1272 -0.0303 0.0523 0.025 Uiso 1 1 d R . .
C4 C 0.05770(15) -0.1448(3) 0.2087(2) 0.0170(4) Uani 1 1 d . . .
C14 C -0.11054(16) -0.3109(3) 0.2244(2) 0.0210(5) Uani 1 1 d . . .
H14A H -0.0760 -0.3213 0.3142 0.025 Uiso 1 1 d R . .
H14B H -0.1165 -0.4171 0.1899 0.025 Uiso 1 1 d R . .
C3 C 0.10033(16) -0.1153(3) 0.1639(2) 0.0209(5) Uani 1 1 d . . .
H3 H 0.0970 -0.1782 0.1058 0.025 Uiso 1 1 d R . .
C15 C 0.0000 0.3181(4) 0.0000 0.0247(8) Uani 1 2 d S . .
H15 H 0.0043 0.2489 -0.0519 0.030 Uiso 1 1 d R . .
N3 N -0.06749(16) -0.1944(3) 0.1964(2) 0.0164(5) Uani 1 1 d . . .
C5 C 0.15666(16) 0.2354(3) 0.3735(2) 0.0203(5) Uani 1 1 d . . .
H5A H 0.2184 0.2633 0.4211 0.024 Uiso 1 1 d R . .
H5B H 0.1209 0.3244 0.3171 0.024 Uiso 1 1 d R . .


_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 N1 2.0259(19) . ?
Sb1 N2 2.4521(19) . ?
Sb1 N3 2.454(2) . ?
Sb1 Cl2 2.5609(6) . ?
Sb1 Cl1 2.5903(7) . ?
N1 C1 1.362(3) . ?
N1 C4 1.374(3) . ?
C2 C1 1.372(3) . ?
C2 C3 1.435(4) . ?
C2 H2 0.9298 . ?
C6 N2 1.490(3) . ?
C6 C7 1.517(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.543(4) . ?
C7 H7A 0.9698 . ?
C7 H7B 0.9701 . ?
C8 C9 1.523(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C5 1.498(3) . ?
Cl3 C15 1.770(2) . ?
N2 C5 1.489(3) . ?
N2 C9 1.492(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9701 . ?
C12 C11 1.514(3) . ?
C12 C13 1.536(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C10 C4 1.490(3) . ?
C10 N3 1.490(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9699 . ?
C13 C14 1.530(4) . ?
C13 H13A 0.9699 . ?
C13 H13B 0.9699 . ?
C11 N3 1.490(3) . ?
C11 H11A 0.9701 . ?
C11 H11B 0.9700 . ?
C4 C3 1.362(3) . ?
C14 N3 1.498(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9699 . ?
C3 H3 0.9300 . ?
C15 Cl3 1.771(2) 2 ?
C15 H15 0.9701 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?

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
N1 Sb1 N2 72.05(7) . . ?
N1 Sb1 N3 73.08(8) . . ?
N2 Sb1 N3 145.05(8) . . ?
N1 Sb1 Cl2 85.89(6) . . ?
N2 Sb1 Cl2 94.68(5) . . ?
N3 Sb1 Cl2 85.02(6) . . ?
N1 Sb1 Cl1 85.96(6) . . ?
N2 Sb1 Cl1 82.77(5) . . ?
N3 Sb1 Cl1 92.62(5) . . ?
Cl2 Sb1 Cl1 171.85(2) . . ?
C1 N1 C4 109.6(2) . . ?
C1 N1 Sb1 124.80(15) . . ?
C4 N1 Sb1 124.04(16) . . ?
C1 C2 C3 106.8(2) . . ?
C1 C2 H2 127.0 . . ?
C3 C2 H2 126.3 . . ?
N2 C6 C7 104.7(2) . . ?
N2 C6 H6A 110.7 . . ?
C7 C6 H6A 110.6 . . ?
N2 C6 H6B 111.0 . . ?
C7 C6 H6B 111.0 . . ?
H6A C6 H6B 108.9 . . ?
C6 C7 C8 105.2(2) . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7A 110.7 . . ?
C6 C7 H7B 110.5 . . ?
C8 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C9 C8 C7 104.6(2) . . ?
C9 C8 H8A 110.8 . . ?
C7 C8 H8A 110.8 . . ?
C9 C8 H8B 111.0 . . ?
C7 C8 H8B 110.7 . . ?
H8A C8 H8B 108.9 . . ?
N1 C1 C2 108.3(2) . . ?
N1 C1 C5 116.6(2) . . ?
C2 C1 C5 134.6(2) . . ?
C5 N2 C6 111.64(19) . . ?
C5 N2 C9 112.68(18) . . ?
C6 N2 C9 102.75(19) . . ?
C5 N2 Sb1 106.45(13) . . ?
C6 N2 Sb1 112.72(14) . . ?
C9 N2 Sb1 110.74(14) . . ?
N2 C9 C8 103.4(2) . . ?
N2 C9 H9A 111.3 . . ?
C8 C9 H9A 111.2 . . ?
N2 C9 H9B 111.0 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 109.0 . . ?
C11 C12 C13 103.4(2) . . ?
C11 C12 H12A 111.0 . . ?
C13 C12 H12A 111.1 . . ?
C11 C12 H12B 111.0 . . ?
C13 C12 H12B 111.2 . . ?
H12A C12 H12B 109.1 . . ?
C4 C10 N3 108.13(19) . . ?
C4 C10 H10A 110.1 . . ?
N3 C10 H10A 110.2 . . ?
C4 C10 H10B 110.0 . . ?
N3 C10 H10B 110.0 . . ?
H10A C10 H10B 108.4 . . ?
C14 C13 C12 105.7(2) . . ?
C14 C13 H13A 110.7 . . ?
C12 C13 H13A 110.6 . . ?
C14 C13 H13B 110.5 . . ?
C12 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
N3 C11 C12 103.4(2) . . ?
N3 C11 H11A 110.9 . . ?
C12 C11 H11A 111.0 . . ?
N3 C11 H11B 111.2 . . ?
C12 C11 H11B 111.3 . . ?
H11A C11 H11B 109.0 . . ?
C3 C4 N1 108.0(2) . . ?
C3 C4 C10 137.1(2) . . ?
N1 C4 C10 114.8(2) . . ?
N3 C14 C13 105.5(2) . . ?
N3 C14 H14A 110.6 . . ?
C13 C14 H14A 110.5 . . ?
N3 C14 H14B 110.7 . . ?
C13 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C4 C3 C2 107.3(2) . . ?
C4 C3 H3 126.1 . . ?
C2 C3 H3 126.6 . . ?
Cl3 C15 Cl3 110.8(2) . 2 ?
Cl3 C15 H15 109.5 . . ?
Cl3 C15 H15 109.5 2 . ?
C10 N3 C11 112.0(2) . . ?
C10 N3 C14 112.7(2) . . ?
C11 N3 C14 103.3(2) . . ?
C10 N3 Sb1 104.72(15) . . ?
C11 N3 Sb1 112.31(17) . . ?
C14 N3 Sb1 112.12(17) . . ?
N2 C5 C1 109.54(19) . . ?
N2 C5 H5A 109.7 . . ?
C1 C5 H5A 109.8 . . ?
N2 C5 H5B 109.8 . . ?
C1 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.075
_database_code_depnum_ccdc_archive 'CCDC 1017117'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 Bi Cl2 N3'
_chemical_formula_sum            'C14 H22 Bi Cl2 N3'
_chemical_formula_weight         512.23

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'
N N 0.0061 0.0033 '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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   8.7020(5)
_cell_length_b                   20.6791(14)
_cell_length_c                   12.1480(7)
_cell_angle_alpha                90
_cell_angle_beta                 132.669(5)
_cell_angle_gamma                90
_cell_volume                     1607.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    13478
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    11.296
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.081
0 1 0 0.120
-1 0 0 0.233
1 0 0 0.231
0 0 1 0.048
0 0 -1 0.065
-1 0 -1 0.172
1 0 -1 0.189
1 -1 0 0.226
-1 1 0 0.207
1 1 0 0.208


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.123
_exptl_absorpt_correction_T_max  0.303
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_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  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13439
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3650
_reflns_number_gt                3383
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0445P)²+9.9607P] 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         3650
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_restrained_S_all      1.216
_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
Bi1 Bi 1.29052(3) 0.088821(10) 0.88241(2) 0.01437(10) Uani 1 1 d . . .
Cl2 Cl 1.4798(3) 0.01473(7) 0.82047(19) 0.0227(3) Uani 1 1 d . . .
Cl1 Cl 1.0996(3) 0.16154(8) 0.9378(2) 0.0276(4) Uani 1 1 d . . .
N1 N 1.0664(9) 0.1202(3) 0.6556(6) 0.0204(11) Uani 1 1 d . . .
C13 C 1.5882(12) 0.2438(4) 1.0588(8) 0.0277(15) Uani 1 1 d . . .
H13A H 1.6360 0.2872 1.0985 0.033 Uiso 1 1 d R . .
H13B H 1.5455 0.2230 1.1060 0.033 Uiso 1 1 d R . .
N2 N 0.9708(8) 0.0191(2) 0.7364(6) 0.0166(10) Uani 1 1 d . . .
N3 N 1.4376(8) 0.1842(2) 0.8403(6) 0.0149(10) Uani 1 1 d . . .
C5 C 0.7924(10) 0.0611(3) 0.6167(8) 0.0208(13) Uani 1 1 d . . .
H5A H 0.7497 0.0875 0.6579 0.025 Uiso 1 1 d R . .
H5B H 0.6744 0.0346 0.5374 0.025 Uiso 1 1 d R . .
C12 C 1.7582(11) 0.2052(4) 1.0861(8) 0.0285(15) Uani 1 1 d . . .
H12A H 1.7998 0.1690 1.1521 0.034 Uiso 1 1 d R . .
H12B H 1.8797 0.2322 1.1324 0.034 Uiso 1 1 d R . .
C1 C 0.8603(10) 0.1032(3) 0.5559(7) 0.0182(12) Uani 1 1 d . . .
C14 C 1.4070(11) 0.2451(3) 0.8893(8) 0.0215(13) Uani 1 1 d . . .
H14A H 1.2731 0.2452 0.8617 0.026 Uiso 1 1 d R . .
H14B H 1.4159 0.2828 0.8463 0.026 Uiso 1 1 d R . .
C10 C 1.3229(11) 0.1842(3) 0.6791(8) 0.0222(13) Uani 1 1 d . . .
H10A H 1.3270 0.2272 0.6491 0.027 Uiso 1 1 d R . .
H10B H 1.3875 0.1544 0.6591 0.027 Uiso 1 1 d R . .
C9 C 0.9810(11) -0.0389(3) 0.6674(8) 0.0195(13) Uani 1 1 d . . .
H9A H 1.1175 -0.0591 0.7376 0.023 Uiso 1 1 d R . .
H9B H 0.9525 -0.0271 0.5777 0.023 Uiso 1 1 d R . .
C2 C 0.7632(10) 0.1350(3) 0.4249(7) 0.0204(13) Uani 1 1 d . . .
H2 H 0.6243 0.1306 0.3362 0.024 Uiso 1 1 d R . .
C11 C 1.6672(11) 0.1816(3) 0.9333(8) 0.0215(13) Uani 1 1 d . . .
H11A H 1.7084 0.2095 0.8929 0.026 Uiso 1 1 d R . .
H11B H 1.7134 0.1378 0.9404 0.026 Uiso 1 1 d R . .
C8 C 0.8080(11) -0.0843(3) 0.6289(9) 0.0230(10) Uani 1 1 d . . .
H8A H 0.6753 -0.0764 0.5282 0.028 Uiso 1 1 d R . .
H8B H 0.8467 -0.1292 0.6371 0.028 Uiso 1 1 d R . .
C4 C 1.1005(10) 0.1644(3) 0.5901(7) 0.0177(12) Uani 1 1 d . . .
C6 C 0.9410(11) -0.0104(3) 0.8325(7) 0.0212(13) Uani 1 1 d . . .
H6A H 0.8781 0.0203 0.8525 0.025 Uiso 1 1 d R . .
H6B H 1.0738 -0.0245 0.9271 0.025 Uiso 1 1 d R . .
C3 C 0.9150(11) 0.1748(3) 0.4468(7) 0.0217(14) Uani 1 1 d . . .
H3 H 0.8929 0.2028 0.3773 0.026 Uiso 1 1 d R . .
C7 C 0.7962(11) -0.0684(3) 0.7448(8) 0.0230(10) Uani 1 1 d . . .
H7A H 0.8405 -0.1050 0.8105 0.028 Uiso 1 1 d R . .
H7B H 0.6538 -0.0574 0.6958 0.028 Uiso 1 1 d R . .


_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 N1 2.129(6) . ?
Bi1 N2 2.505(5) . ?
Bi1 N3 2.584(5) . ?
Bi1 Cl1 2.6438(16) . ?
Bi1 Cl2 2.7029(16) . ?
N1 C1 1.365(8) . ?
N1 C4 1.369(8) . ?
C13 C12 1.507(11) . ?
C13 C14 1.525(10) . ?
C13 H13A 0.9701 . ?
C13 H13B 0.9701 . ?
N2 C6 1.488(8) . ?
N2 C5 1.489(8) . ?
N2 C9 1.499(8) . ?
N3 C10 1.477(8) . ?
N3 C11 1.487(8) . ?
N3 C14 1.492(8) . ?
C5 C1 1.498(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C12 C11 1.523(10) . ?
C12 H12A 0.9699 . ?
C12 H12B 0.9700 . ?
C1 C2 1.363(9) . ?
C14 H14A 0.9699 . ?
C14 H14B 0.9701 . ?
C10 C4 1.499(10) . ?
C10 H10A 0.9701 . ?
C10 H10B 0.9700 . ?
C9 C8 1.554(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C2 C3 1.421(10) . ?
C2 H2 0.9300 . ?
C11 H11A 0.9699 . ?
C11 H11B 0.9701 . ?
C8 C7 1.516(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9699 . ?
C4 C3 1.369(9) . ?
C6 C7 1.531(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C3 H3 0.9300 . ?
C7 H7A 0.9701 . ?
C7 H7B 0.9700 . ?

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
N1 Bi1 N2 69.86(19) . . ?
N1 Bi1 N3 69.69(19) . . ?
N2 Bi1 N3 139.50(17) . . ?
N1 Bi1 Cl1 88.47(16) . . ?
N2 Bi1 Cl1 85.40(13) . . ?
N3 Bi1 Cl1 95.59(12) . . ?
N1 Bi1 Cl2 90.53(16) . . ?
N2 Bi1 Cl2 94.04(12) . . ?
N3 Bi1 Cl2 84.28(12) . . ?
Cl1 Bi1 Cl2 178.98(5) . . ?
C1 N1 C4 109.2(5) . . ?
C1 N1 Bi1 124.7(4) . . ?
C4 N1 Bi1 125.9(4) . . ?
C12 C13 C14 105.6(6) . . ?
C12 C13 H13A 110.8 . . ?
C14 C13 H13A 110.9 . . ?
C12 C13 H13B 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.8 . . ?
C6 N2 C5 112.6(5) . . ?
C6 N2 C9 102.7(5) . . ?
C5 N2 C9 109.7(5) . . ?
C6 N2 Bi1 112.4(4) . . ?
C5 N2 Bi1 106.2(4) . . ?
C9 N2 Bi1 113.4(4) . . ?
C10 N3 C11 111.1(5) . . ?
C10 N3 C14 112.7(5) . . ?
C11 N3 C14 103.8(5) . . ?
C10 N3 Bi1 106.4(4) . . ?
C11 N3 Bi1 114.4(4) . . ?
C14 N3 Bi1 108.6(4) . . ?
N2 C5 C1 108.8(5) . . ?
N2 C5 H5A 109.6 . . ?
C1 C5 H5A 110.1 . . ?
N2 C5 H5B 110.0 . . ?
C1 C5 H5B 110.1 . . ?
H5A C5 H5B 108.3 . . ?
C13 C12 C11 106.2(6) . . ?
C13 C12 H12A 110.6 . . ?
C11 C12 H12A 110.8 . . ?
C13 C12 H12B 110.1 . . ?
C11 C12 H12B 110.7 . . ?
H12A C12 H12B 108.5 . . ?
C2 C1 N1 108.2(6) . . ?
C2 C1 C5 135.8(6) . . ?
N1 C1 C5 115.7(6) . . ?
N3 C14 C13 102.9(5) . . ?
N3 C14 H14A 111.2 . . ?
C13 C14 H14A 111.5 . . ?
N3 C14 H14B 111.2 . . ?
C13 C14 H14B 110.8 . . ?
H14A C14 H14B 109.1 . . ?
N3 C10 C4 109.7(5) . . ?
N3 C10 H10A 109.6 . . ?
C4 C10 H10A 109.8 . . ?
N3 C10 H10B 110.2 . . ?
C4 C10 H10B 109.3 . . ?
H10A C10 H10B 108.2 . . ?
N2 C9 C8 103.8(5) . . ?
N2 C9 H9A 110.8 . . ?
C8 C9 H9A 111.3 . . ?
N2 C9 H9B 111.2 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C1 C2 C3 107.4(6) . . ?
C1 C2 H2 126.6 . . ?
C3 C2 H2 125.9 . . ?
N3 C11 C12 103.6(6) . . ?
N3 C11 H11A 111.2 . . ?
C12 C11 H11A 111.1 . . ?
N3 C11 H11B 111.3 . . ?
C12 C11 H11B 110.4 . . ?
H11A C11 H11B 109.2 . . ?
C7 C8 C9 104.6(5) . . ?
C7 C8 H8A 111.3 . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8B 110.4 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.9 . . ?
N1 C4 C3 108.1(6) . . ?
N1 C4 C10 116.5(6) . . ?
C3 C4 C10 135.0(6) . . ?
N2 C6 C7 105.9(5) . . ?
N2 C6 H6A 110.9 . . ?
C7 C6 H6A 110.4 . . ?
N2 C6 H6B 110.5 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.8 . . ?
C4 C3 C2 107.0(6) . . ?
C4 C3 H3 126.4 . . ?
C2 C3 H3 126.7 . . ?
C8 C7 C6 105.9(5) . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7A 111.0 . . ?
C8 C7 H7B 110.0 . . ?
C6 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         3.800
_refine_diff_density_min         -3.006
_refine_diff_density_rms         0.262
_database_code_depnum_ccdc_archive 'CCDC 1017118'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H18 Cl2 N3 Sb, C H2 Cl2'
_chemical_formula_sum            'C11 H20 Cl4 N3 Sb'
_chemical_formula_weight         457.85

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.6800(7)
_cell_length_b                   26.242(2)
_cell_length_c                   16.6360(12)
_cell_angle_alpha                90
_cell_angle_beta                 113.379(8)
_cell_angle_gamma                90
_cell_volume                     3478.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    24490
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.29
_exptl_absorpt_coefficient_mu    2.192
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.219
-1 0 0 0.173
0 -1 1 0.147
0 1 -1 0.129
0 1 1 0.157
0 -1 -1 0.135
0 1 0 0.214
0 -1 0 0.231


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.455
_exptl_absorpt_correction_T_max  0.635
_exptl_absorpt_process_details   
;
Gaussian integration (Coppens, 1970)
;

_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  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_reflns_number            24447
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.556
_diffrn_reflns_theta_max         27.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             7647
_reflns_number_gt                6952
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0193P)²+7.9434P] 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         7647
_refine_ls_number_parameters     352
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.178
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.26001(2) 0.23046(2) 0.43487(2) 0.01619(6) Uani 1 1 d . . . . .
Sb2 Sb 0.52969(3) 0.06713(2) 0.61039(2) 0.01754(6) Uani 1 1 d . . . . .
Cl1 Cl 0.03837(10) 0.29421(3) 0.43641(6) 0.02542(17) Uani 1 1 d . . . . .
Cl2 Cl 0.47265(11) 0.16644(3) 0.41410(6) 0.03089(19) Uani 1 1 d . . . . .
Cl4 Cl 0.76419(12) 0.00154(3) 0.62397(7) 0.0338(2) Uani 1 1 d . . . . .
Cl3 Cl 0.31414(11) 0.13141(3) 0.61783(6) 0.02879(18) Uani 1 1 d . . . . .
N1 N 0.1595(3) 0.23640(10) 0.30212(17) 0.0185(5) Uani 1 1 d . . . . .
N4 N 0.6172(3) 0.06354(10) 0.74307(17) 0.0202(5) Uani 1 1 d . . . . .
C108 C 0.8692(4) 0.10855(14) 0.7572(2) 0.0268(7) Uani 1 1 d . . . . .
108A H 0.9453 0.0828 0.7523 0.032 Uiso 1 1 d R U . . .
108B H 0.9356 0.1364 0.7923 0.032 Uiso 1 1 d R U . . .
C106 C 0.1830(5) 0.00474(16) 0.5856(3) 0.0352(9) Uani 1 1 d . . . . .
106A H 0.1783 -0.0033 0.5284 0.042 Uiso 1 1 d R U . . .
106B H 0.1348 0.0378 0.5845 0.042 Uiso 1 1 d R U . . .
106C H 0.1211 -0.0203 0.6027 0.042 Uiso 1 1 d R U . . .
N5 N 0.3600(4) 0.00482(11) 0.6499(2) 0.0252(6) Uani 1 1 d . . . . .
C110 C 0.8531(5) 0.13035(15) 0.6112(2) 0.0300(8) Uani 1 1 d . . . . .
110A H 0.7795 0.1414 0.5538 0.036 Uiso 1 1 d R U . . .
110B H 0.8976 0.0974 0.6075 0.036 Uiso 1 1 d R U . . .
110C H 0.9436 0.1542 0.6356 0.036 Uiso 1 1 d R U . . .
N6 N 0.7589(3) 0.12733(10) 0.66823(18) 0.0224(6) Uani 1 1 d . . . . .
N3 N 0.4200(3) 0.29546(10) 0.39376(18) 0.0205(5) Uani 1 1 d . . . . .
C102 C 0.6324(5) 0.04914(13) 0.8767(2) 0.0284(8) Uani 1 1 d . . . . .
H102 H 0.6078 0.0379 0.9233 0.034 Uiso 1 1 d R U . . .
N2 N 0.0244(3) 0.17093(10) 0.37798(18) 0.0202(5) Uani 1 1 d . . . . .
C104 C 0.7627(4) 0.08620(13) 0.7992(2) 0.0225(7) Uani 1 1 d . . . . .
C1 C 0.0129(4) 0.21455(12) 0.2478(2) 0.0203(6) Uani 1 1 d . . . . .
C2 C -0.0065(4) 0.22449(13) 0.1630(2) 0.0250(7) Uani 1 1 d . . . . .
H2 H -0.0953 0.2141 0.1123 0.030 Uiso 1 1 d R U . . .
C10 C 0.5981(4) 0.29643(15) 0.4549(2) 0.0295(8) Uani 1 1 d . . . . .
H10A H 0.6588 0.3189 0.4324 0.035 Uiso 1 1 d R U . . .
H10B H 0.6439 0.2627 0.4605 0.035 Uiso 1 1 d R U . . .
H10C H 0.6077 0.3083 0.5113 0.035 Uiso 1 1 d R U . . .
C4 C 0.2347(4) 0.26008(12) 0.2538(2) 0.0210(6) Uani 1 1 d . . . . .
C6 C -0.0666(4) 0.16632(14) 0.4365(2) 0.0266(7) Uani 1 1 d . . . . .
H6A H -0.1033 0.1994 0.4462 0.032 Uiso 1 1 d R U . . .
H6B H 0.0069 0.1520 0.4914 0.032 Uiso 1 1 d R U . . .
H6C H -0.1622 0.1445 0.4097 0.032 Uiso 1 1 d R U . . .
C8 C 0.4060(4) 0.28067(14) 0.3044(2) 0.0255(7) Uani 1 1 d . . . . .
H8A H 0.4257 0.3102 0.2746 0.031 Uiso 1 1 d R U . . .
H8B H 0.4897 0.2551 0.3089 0.031 Uiso 1 1 d R U . . .
C7 C 0.0869(4) 0.12004(12) 0.3665(2) 0.0263(7) Uani 1 1 d . . . . .
H7A H -0.0058 0.0968 0.3440 0.032 Uiso 1 1 d R U . . .
H7B H 0.1658 0.1080 0.4221 0.032 Uiso 1 1 d R U . . .
H7C H 0.1409 0.1223 0.3263 0.032 Uiso 1 1 d R U . . .
C5 C -0.0898(4) 0.19130(13) 0.2911(2) 0.0230(7) Uani 1 1 d . . . . .
H5A H -0.1576 0.1639 0.2551 0.028 Uiso 1 1 d R U . . .
H5B H -0.1644 0.2166 0.2986 0.028 Uiso 1 1 d R U . . .
C103 C 0.7752(5) 0.07785(14) 0.8826(2) 0.0280(7) Uani 1 1 d . . . . .
H103 H 0.8613 0.0889 0.9339 0.034 Uiso 1 1 d R U . . .
C9 C 0.3458(5) 0.34638(13) 0.3896(3) 0.0292(8) Uani 1 1 d . . . . .
H9A H 0.3559 0.3564 0.4469 0.035 Uiso 1 1 d R U . . .
H9B H 0.2294 0.3455 0.3506 0.035 Uiso 1 1 d R U . . .
H9C H 0.4040 0.3704 0.3682 0.035 Uiso 1 1 d R U . . .
C101 C 0.5375(4) 0.04118(12) 0.7900(2) 0.0225(7) Uani 1 1 d . . . . .
C109 C 0.6955(5) 0.17850(13) 0.6763(3) 0.0305(8) Uani 1 1 d . . . . .
109A H 0.7881 0.2018 0.6992 0.037 Uiso 1 1 d R U . . .
109B H 0.6383 0.1771 0.7152 0.037 Uiso 1 1 d R U . . .
109C H 0.6190 0.1899 0.6197 0.037 Uiso 1 1 d R U . . .
C105 C 0.3678(5) 0.02005(14) 0.7376(2) 0.0277(7) Uani 1 1 d . . . . .
105A H 0.2824 0.0453 0.7316 0.033 Uiso 1 1 d R U . . .
105B H 0.3474 -0.0095 0.7670 0.033 Uiso 1 1 d R U . . .
C3 C 0.1347(4) 0.25376(13) 0.1676(2) 0.0239(7) Uani 1 1 d . . . . .
H3 H 0.1553 0.2662 0.1204 0.029 Uiso 1 1 d R U . . .
C107 C 0.4331(5) -0.04627(13) 0.6538(3) 0.0346(9) Uani 1 1 d . . . . .
107A H 0.3694 -0.0707 0.6709 0.042 Uiso 1 1 d R U . . .
107B H 0.5473 -0.0462 0.6958 0.042 Uiso 1 1 d R U . . .
107C H 0.4300 -0.0552 0.5972 0.042 Uiso 1 1 d R U . . .
Cl6 Cl 0.48075(14) 0.19275(6) 0.14909(8) 0.0568(3) Uani 1 1 d . . . . .
Cl7 Cl 0.81533(18) -0.02073(6) 0.09754(9) 0.0641(4) Uani 1 1 d . U . . .
Cl5 Cl 0.3506(3) 0.08870(5) 0.11722(11) 0.0885(6) Uani 1 1 d . . . . .
Cl8 Cl 0.8835(17) 0.0811(4) 0.1297(9) 0.091(3) Uani 0.5 1 d . U P A 1
C11 C 0.3234(7) 0.15021(17) 0.1503(3) 0.0498(12) Uani 1 1 d . . . . .
H11A H 0.3250 0.1487 0.2089 0.060 Uiso 1 1 d R U . . .
H11B H 0.2145 0.1630 0.1113 0.060 Uiso 1 1 d R U . . .
C12 C 0.9815(9) 0.0228(2) 0.1329(4) 0.0702(17) Uani 1 1 d . U . . .
H12A H 1.0605 0.0149 0.1919 0.084 Uiso 1 1 calc R U . A 1
H12B H 1.0405 0.0228 0.0941 0.084 Uiso 1 1 calc R U . A 1
Cl8A Cl 0.9437(17) 0.0902(4) 0.1307(9) 0.074(2) Uani 0.5 1 d . U P A 2


_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 N1 2.033(3) . ?
Sb1 N2 2.446(3) . ?
Sb1 N3 2.462(3) . ?
Sb1 Cl1 2.5574(8) . ?
Sb1 Cl2 2.6181(9) . ?
Sb2 N4 2.032(3) . ?
Sb2 N6 2.421(3) . ?
Sb2 N5 2.459(3) . ?
Sb2 Cl3 2.5583(9) . ?
Sb2 Cl4 2.6061(9) . ?
N1 C1 1.361(4) . ?
N1 C4 1.369(4) . ?
N4 C101 1.364(4) . ?
N4 C104 1.373(4) . ?
C108 C104 1.484(5) . ?
C108 N6 1.491(4) . ?
C108 108A 0.9700 . ?
C108 108B 0.9699 . ?
C106 N5 1.483(5) . ?
C106 106A 0.9600 . ?
C106 106B 0.9600 . ?
C106 106C 0.9601 . ?
N5 C107 1.474(5) . ?
N5 C105 1.487(4) . ?
C110 N6 1.480(4) . ?
C110 110A 0.9599 . ?
C110 110B 0.9600 . ?
C110 110C 0.9601 . ?
N6 C109 1.477(4) . ?
N3 C9 1.473(4) . ?
N3 C10 1.475(4) . ?
N3 C8 1.494(4) . ?
C102 C101 1.365(5) . ?
C102 C103 1.420(5) . ?
C102 H102 0.9301 . ?
N2 C6 1.482(4) . ?
N2 C7 1.482(4) . ?
N2 C5 1.490(4) . ?
C104 C103 1.365(5) . ?
C1 C2 1.378(5) . ?
C1 C5 1.482(5) . ?
C2 C3 1.423(5) . ?
C2 H2 0.9300 . ?
C10 H10A 0.9602 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9599 . ?
C4 C3 1.361(5) . ?
C4 C8 1.489(5) . ?
C6 H6A 0.9602 . ?
C6 H6B 0.9599 . ?
C6 H6C 0.9599 . ?
C8 H8A 0.9699 . ?
C8 H8B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9601 . ?
C5 H5A 0.9699 . ?
C5 H5B 0.9700 . ?
C103 H103 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9601 . ?
C101 C105 1.489(5) . ?
C109 109A 0.9600 . ?
C109 109B 0.9599 . ?
C109 109C 0.9600 . ?
C105 105A 0.9700 . ?
C105 105B 0.9700 . ?
C3 H3 0.9299 . ?
C107 107A 0.9600 . ?
C107 107B 0.9600 . ?
C107 107C 0.9600 . ?
Cl6 C11 1.770(5) . ?
Cl7 C12 1.749(6) . ?
Cl5 C11 1.752(4) . ?
Cl8 C12 1.740(15) . ?
C11 H11A 0.9701 . ?
C11 H11B 0.9699 . ?
C12 Cl8A 1.797(13) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
N1 Sb1 N2 72.31(10) . . ?
N1 Sb1 N3 72.03(10) . . ?
N2 Sb1 N3 144.33(9) . . ?
N1 Sb1 Cl1 87.73(8) . . ?
N2 Sb1 Cl1 84.55(7) . . ?
N3 Sb1 Cl1 93.39(7) . . ?
N1 Sb1 Cl2 85.82(8) . . ?
N2 Sb1 Cl2 93.67(7) . . ?
N3 Sb1 Cl2 84.43(7) . . ?
Cl1 Sb1 Cl2 173.54(3) . . ?
N4 Sb2 N6 72.81(10) . . ?
N4 Sb2 N5 71.57(10) . . ?
N6 Sb2 N5 144.37(10) . . ?
N4 Sb2 Cl3 86.75(8) . . ?
N6 Sb2 Cl3 92.98(7) . . ?
N5 Sb2 Cl3 84.16(7) . . ?
N4 Sb2 Cl4 86.14(8) . . ?
N6 Sb2 Cl4 84.61(7) . . ?
N5 Sb2 Cl4 93.89(7) . . ?
Cl3 Sb2 Cl4 172.89(3) . . ?
C1 N1 C4 109.8(3) . . ?
C1 N1 Sb1 125.1(2) . . ?
C4 N1 Sb1 125.0(2) . . ?
C101 N4 C104 109.6(3) . . ?
C101 N4 Sb2 125.8(2) . . ?
C104 N4 Sb2 124.4(2) . . ?
C104 C108 N6 108.9(3) . . ?
C104 C108 108A 109.6 . . ?
N6 C108 108A 109.8 . . ?
C104 C108 108B 110.2 . . ?
N6 C108 108B 110.1 . . ?
108A C108 108B 108.3 . . ?
N5 C106 106A 109.9 . . ?
N5 C106 106B 109.3 . . ?
106A C106 106B 109.5 . . ?
N5 C106 106C 109.2 . . ?
106A C106 106C 109.5 . . ?
106B C106 106C 109.5 . . ?
C107 N5 C106 109.6(3) . . ?
C107 N5 C105 110.5(3) . . ?
C106 N5 C105 109.8(3) . . ?
C107 N5 Sb2 108.9(2) . . ?
C106 N5 Sb2 111.5(2) . . ?
C105 N5 Sb2 106.54(19) . . ?
N6 C110 110A 109.6 . . ?
N6 C110 110B 109.4 . . ?
110A C110 110B 109.5 . . ?
N6 C110 110C 109.4 . . ?
110A C110 110C 109.5 . . ?
110B C110 110C 109.5 . . ?
C109 N6 C110 109.3(3) . . ?
C109 N6 C108 109.0(3) . . ?
C110 N6 C108 110.6(3) . . ?
C109 N6 Sb2 110.6(2) . . ?
C110 N6 Sb2 110.9(2) . . ?
C108 N6 Sb2 106.35(19) . . ?
C9 N3 C10 109.6(3) . . ?
C9 N3 C8 109.1(3) . . ?
C10 N3 C8 109.9(3) . . ?
C9 N3 Sb1 110.9(2) . . ?
C10 N3 Sb1 111.9(2) . . ?
C8 N3 Sb1 105.32(19) . . ?
C101 C102 C103 107.4(3) . . ?
C101 C102 H102 126.2 . . ?
C103 C102 H102 126.4 . . ?
C6 N2 C7 109.2(3) . . ?
C6 N2 C5 110.1(3) . . ?
C7 N2 C5 109.6(3) . . ?
C6 N2 Sb1 112.3(2) . . ?
C7 N2 Sb1 109.46(19) . . ?
C5 N2 Sb1 106.18(18) . . ?
C103 C104 N4 107.6(3) . . ?
C103 C104 C108 136.8(3) . . ?
N4 C104 C108 115.3(3) . . ?
N1 C1 C2 107.6(3) . . ?
N1 C1 C5 115.8(3) . . ?
C2 C1 C5 136.3(3) . . ?
C1 C2 C3 107.1(3) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 H2 126.4 . . ?
N3 C10 H10A 109.2 . . ?
N3 C10 H10B 109.3 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.9 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C4 N1 108.1(3) . . ?
C3 C4 C8 135.7(3) . . ?
N1 C4 C8 115.8(3) . . ?
N2 C6 H6A 109.6 . . ?
N2 C6 H6B 109.4 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C8 N3 109.0(3) . . ?
C4 C8 H8A 109.9 . . ?
N3 C8 H8A 109.8 . . ?
C4 C8 H8B 110.0 . . ?
N3 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
N2 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.8 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C5 N2 108.8(3) . . ?
C1 C5 H5A 109.8 . . ?
N2 C5 H5A 109.9 . . ?
C1 C5 H5B 110.0 . . ?
N2 C5 H5B 110.0 . . ?
H5A C5 H5B 108.3 . . ?
C104 C103 C102 107.5(3) . . ?
C104 C103 H103 126.3 . . ?
C102 C103 H103 126.2 . . ?
N3 C9 H9A 109.7 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.3 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C101 C102 108.0(3) . . ?
N4 C101 C105 115.7(3) . . ?
C102 C101 C105 135.9(3) . . ?
N6 C109 109A 109.3 . . ?
N6 C109 109B 109.7 . . ?
109A C109 109B 109.5 . . ?
N6 C109 109C 109.4 . . ?
109A C109 109C 109.5 . . ?
109B C109 109C 109.5 . . ?
N5 C105 C101 108.9(3) . . ?
N5 C105 105A 110.3 . . ?
C101 C105 105A 110.0 . . ?
N5 C105 105B 109.5 . . ?
C101 C105 105B 109.8 . . ?
105A C105 105B 108.3 . . ?
C4 C3 C2 107.3(3) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.4 . . ?
N5 C107 107A 109.3 . . ?
N5 C107 107B 109.5 . . ?
107A C107 107B 109.5 . . ?
N5 C107 107C 109.6 . . ?
107A C107 107C 109.5 . . ?
107B C107 107C 109.5 . . ?
Cl5 C11 Cl6 112.1(3) . . ?
Cl5 C11 H11A 109.2 . . ?
Cl6 C11 H11A 109.5 . . ?
Cl5 C11 H11B 109.0 . . ?
Cl6 C11 H11B 109.0 . . ?
H11A C11 H11B 107.9 . . ?
Cl8 C12 Cl7 103.6(5) . . ?
Cl7 C12 Cl8A 121.1(5) . . ?
Cl8 C12 H12A 111.0 . . ?
Cl7 C12 H12A 111.0 . . ?
Cl8 C12 H12B 111.0 . . ?
Cl7 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?

_refine_diff_density_max         0.949
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.123



_database_code_depnum_ccdc_archive 'CCDC 1017119'
