# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222

_publ_contact_author_name        'Cristian Silvestru'
_publ_contact_author_email       CRISTI@CHEM.UBBCLUJ.RO

_publ_section_title              
;
Monoorganobismuth(III) dihalides containing the new
pincer 2,6-{MeN(CH2CH2)2NCH2}2C6H3 ligand: solution NMR, vibrational and
single-crystal X-ray studies
;
loop_
_publ_author_name
'Cristian Silvestru'
'Massimiliano Arca'
'Hans J Breunig'
'Vito Lippolis'
'Albert Soran'

# Attachment '619312 - 682012 - 682013.cif'

data_619312
_database_code_depnum_ccdc_archive 'CCDC 619312'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H29 Bi Cl2 N4'
_chemical_formula_weight         581.33

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   '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                   8.4030(10)
_cell_length_b                   14.9333(19)
_cell_length_c                   17.673(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.263(2)
_cell_angle_gamma                90.00
_cell_volume                     2158.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    7029
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      26.88

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    8.424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.204
_exptl_absorpt_correction_T_max  0.400
_exptl_absorpt_process_details   'Bruker, 2001.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(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            22803
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         26.37
_reflns_number_total             4413
_reflns_number_gt                4168
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0136P)^2^+6.3099P] 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         4413
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0720
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_restrained_S_all      1.229
_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 0.87016(2) 0.778632(14) 0.760612(11) 0.02701(7) Uani 1 1 d . . .
C1 C 0.9397(6) 0.6396(4) 0.7899(3) 0.0264(11) Uani 1 1 d . . .
C2 C 1.0606(7) 0.5995(4) 0.7583(3) 0.0315(12) Uani 1 1 d . . .
C3 C 1.0978(8) 0.5092(4) 0.7739(4) 0.0431(15) Uani 1 1 d . . .
H3 H 1.1745 0.4805 0.7520 0.052 Uiso 1 1 calc R . .
C4 C 1.0190(9) 0.4631(5) 0.8224(4) 0.0531(18) Uani 1 1 d . . .
H4 H 1.0468 0.4036 0.8343 0.064 Uiso 1 1 calc R . .
C5 C 0.9004(8) 0.5027(4) 0.8537(4) 0.0473(16) Uani 1 1 d . . .
H5 H 0.8485 0.4699 0.8858 0.057 Uiso 1 1 calc R . .
C6 C 0.8587(7) 0.5917(4) 0.8372(3) 0.0351(13) Uani 1 1 d . . .
C7 C 1.1504(7) 0.6557(4) 0.7113(3) 0.0377(14) Uani 1 1 d . . .
H7A H 1.2427 0.6844 0.7458 0.045 Uiso 1 1 calc R . .
H7B H 1.1925 0.6174 0.6760 0.045 Uiso 1 1 calc R . .
C8 C 0.7231(8) 0.6376(4) 0.8643(4) 0.0406(15) Uani 1 1 d . . .
H8A H 0.6214 0.6287 0.8260 0.049 Uiso 1 1 calc R . .
H8B H 0.7114 0.6103 0.9126 0.049 Uiso 1 1 calc R . .
C9 C 0.9357(7) 0.6859(4) 0.5953(3) 0.0366(14) Uani 1 1 d . . .
H9A H 0.8632 0.6425 0.6108 0.044 Uiso 1 1 calc R . .
H9B H 1.0025 0.6544 0.5658 0.044 Uiso 1 1 calc R . .
C10 C 0.8355(8) 0.7553(4) 0.5446(3) 0.0412(15) Uani 1 1 d . . .
H10A H 0.7703 0.7269 0.4984 0.049 Uiso 1 1 calc R . .
H10B H 0.7616 0.7833 0.5723 0.049 Uiso 1 1 calc R . .
C11 C 1.0412(8) 0.8643(4) 0.5913(3) 0.0403(15) Uani 1 1 d . . .
H11A H 0.9718 0.8935 0.6207 0.048 Uiso 1 1 calc R . .
H11B H 1.1105 0.9095 0.5760 0.048 Uiso 1 1 calc R . .
C12 C 1.1457(7) 0.7961(4) 0.6415(4) 0.0374(14) Uani 1 1 d . . .
H12A H 1.2194 0.7690 0.6131 0.045 Uiso 1 1 calc R . .
H12B H 1.2113 0.8251 0.6873 0.045 Uiso 1 1 calc R . .
C14 C 0.5965(7) 0.7812(5) 0.8783(4) 0.0413(15) Uani 1 1 d . . .
H14A H 0.5447 0.7517 0.9152 0.050 Uiso 1 1 calc R . .
H14B H 0.5230 0.7773 0.8273 0.050 Uiso 1 1 calc R . .
C15 C 0.6258(7) 0.8780(5) 0.9006(4) 0.0426(16) Uani 1 1 d . . .
H15A H 0.6737 0.9082 0.8626 0.051 Uiso 1 1 calc R . .
H15B H 0.5223 0.9068 0.9007 0.051 Uiso 1 1 calc R . .
C16 C 0.8910(7) 0.8465(4) 0.9730(3) 0.0399(14) Uani 1 1 d . . .
H16A H 0.9677 0.8527 1.0228 0.048 Uiso 1 1 calc R . .
H16B H 0.9353 0.8779 0.9344 0.048 Uiso 1 1 calc R . .
C17 C 0.8706(8) 0.7489(4) 0.9518(3) 0.0376(14) Uani 1 1 d . . .
H17A H 0.9756 0.7243 0.9485 0.045 Uiso 1 1 calc R . .
H17B H 0.8337 0.7170 0.9924 0.045 Uiso 1 1 calc R . .
C13 C 0.8429(9) 0.8888(5) 0.4694(4) 0.059(2) Uani 1 1 d . . .
H13A H 0.7809 0.8587 0.4241 0.088 Uiso 1 1 calc R . .
H13B H 0.9145 0.9317 0.4541 0.088 Uiso 1 1 calc R . .
H13C H 0.7697 0.9189 0.4954 0.088 Uiso 1 1 calc R . .
C18 C 0.7563(9) 0.9792(5) 1.0018(5) 0.060(2) Uani 1 1 d . . .
H18A H 0.7999 1.0127 0.9648 0.090 Uiso 1 1 calc R . .
H18B H 0.8307 0.9823 1.0519 0.090 Uiso 1 1 calc R . .
H18C H 0.6528 1.0041 1.0051 0.090 Uiso 1 1 calc R . .
Cl1 Cl 1.16441(18) 0.83358(12) 0.84181(9) 0.0440(4) Uani 1 1 d . . .
Cl2 Cl 0.58227(18) 0.71339(12) 0.67832(9) 0.0463(4) Uani 1 1 d . . .
N1 N 1.0428(5) 0.7254(3) 0.6656(3) 0.0305(10) Uani 1 1 d . . .
N2 N 0.9396(6) 0.8232(4) 0.5220(3) 0.0400(12) Uani 1 1 d . . .
N3 N 0.7520(5) 0.7351(3) 0.8769(3) 0.0312(11) Uani 1 1 d . . .
N4 N 0.7344(6) 0.8862(4) 0.9771(3) 0.0393(12) 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 0.02403(11) 0.02990(12) 0.02706(11) -0.00013(9) 0.00579(8) 0.00047(9)
C1 0.026(3) 0.026(3) 0.026(3) 0.003(2) 0.002(2) 0.006(2)
C2 0.029(3) 0.034(3) 0.030(3) -0.001(2) 0.003(2) 0.001(2)
C3 0.041(4) 0.035(4) 0.054(4) -0.001(3) 0.013(3) 0.011(3)
C4 0.053(4) 0.036(4) 0.070(5) 0.014(3) 0.015(4) 0.003(3)
C5 0.052(4) 0.036(4) 0.055(4) 0.011(3) 0.013(3) -0.005(3)
C6 0.035(3) 0.036(3) 0.034(3) 0.003(3) 0.009(3) -0.007(3)
C7 0.034(3) 0.042(4) 0.040(3) 0.004(3) 0.014(3) 0.008(3)
C8 0.040(3) 0.042(4) 0.044(4) 0.002(3) 0.019(3) -0.009(3)
C9 0.041(3) 0.040(4) 0.030(3) -0.009(3) 0.011(3) -0.003(3)
C10 0.043(4) 0.054(4) 0.026(3) -0.007(3) 0.005(3) -0.001(3)
C11 0.042(3) 0.043(4) 0.039(3) 0.001(3) 0.015(3) -0.002(3)
C12 0.031(3) 0.043(4) 0.040(3) 0.002(3) 0.013(3) -0.001(3)
C14 0.027(3) 0.060(4) 0.038(3) -0.006(3) 0.012(3) 0.004(3)
C15 0.024(3) 0.058(4) 0.048(4) 0.005(3) 0.011(3) 0.013(3)
C16 0.041(3) 0.051(4) 0.026(3) -0.002(3) 0.005(3) 0.000(3)
C17 0.039(3) 0.046(4) 0.028(3) 0.004(3) 0.009(3) 0.004(3)
C13 0.066(5) 0.061(5) 0.047(4) 0.010(4) 0.010(4) 0.019(4)
C18 0.053(4) 0.052(5) 0.078(5) -0.016(4) 0.021(4) 0.000(4)
Cl1 0.0325(8) 0.0603(10) 0.0381(8) -0.0063(7) 0.0056(6) -0.0095(7)
Cl2 0.0310(8) 0.0633(11) 0.0414(8) -0.0092(8) 0.0019(6) -0.0057(7)
N1 0.026(2) 0.034(3) 0.031(2) 0.001(2) 0.0051(19) 0.001(2)
N2 0.048(3) 0.045(3) 0.029(3) 0.004(2) 0.013(2) 0.008(3)
N3 0.026(2) 0.037(3) 0.032(2) 0.000(2) 0.010(2) -0.003(2)
N4 0.037(3) 0.044(3) 0.038(3) -0.007(2) 0.012(2) -0.001(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
Bi1 C1 2.187(5) . ?
Bi1 N3 2.563(4) . ?
Bi1 N1 2.583(5) . ?
Bi1 Cl1 2.6866(15) . ?
Bi1 Cl2 2.7024(15) . ?
C1 C6 1.391(8) . ?
C1 C2 1.402(7) . ?
C2 C3 1.397(8) . ?
C2 C7 1.500(8) . ?
C3 C4 1.380(9) . ?
C4 C5 1.380(10) . ?
C5 C6 1.388(8) . ?
C6 C8 1.500(8) . ?
C7 N1 1.490(7) . ?
C8 N3 1.484(7) . ?
C9 N1 1.480(7) . ?
C9 C10 1.497(9) . ?
C10 N2 1.454(8) . ?
C11 N2 1.458(8) . ?
C11 C12 1.496(8) . ?
C12 N1 1.487(7) . ?
C14 N3 1.483(7) . ?
C14 C15 1.503(9) . ?
C15 N4 1.452(8) . ?
C16 N4 1.460(7) . ?
C16 C17 1.504(9) . ?
C17 N3 1.477(7) . ?
C13 N2 1.462(8) . ?
C18 N4 1.456(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Bi1 N3 72.59(18) . . ?
C1 Bi1 N1 72.69(17) . . ?
N3 Bi1 N1 145.26(15) . . ?
C1 Bi1 Cl1 90.01(14) . . ?
N3 Bi1 Cl1 97.33(11) . . ?
N1 Bi1 Cl1 81.71(11) . . ?
C1 Bi1 Cl2 86.72(14) . . ?
N3 Bi1 Cl2 82.90(11) . . ?
N1 Bi1 Cl2 96.09(11) . . ?
Cl1 Bi1 Cl2 176.50(5) . . ?
C6 C1 C2 121.3(5) . . ?
C6 C1 Bi1 119.3(4) . . ?
C2 C1 Bi1 119.4(4) . . ?
C3 C2 C1 118.9(5) . . ?
C3 C2 C7 122.1(5) . . ?
C1 C2 C7 119.0(5) . . ?
C4 C3 C2 119.2(6) . . ?
C5 C4 C3 121.9(6) . . ?
C4 C5 C6 119.8(6) . . ?
C5 C6 C1 119.0(6) . . ?
C5 C6 C8 122.9(5) . . ?
C1 C6 C8 118.0(5) . . ?
N1 C7 C2 111.8(5) . . ?
N3 C8 C6 112.7(5) . . ?
N1 C9 C10 112.1(5) . . ?
N2 C10 C9 110.9(5) . . ?
N2 C11 C12 111.3(5) . . ?
N1 C12 C11 110.6(5) . . ?
N3 C14 C15 111.1(5) . . ?
N4 C15 C14 110.8(5) . . ?
N4 C16 C17 110.7(5) . . ?
N3 C17 C16 112.0(5) . . ?
C9 N1 C12 108.9(4) . . ?
C9 N1 C7 110.6(5) . . ?
C12 N1 C7 109.3(4) . . ?
C9 N1 Bi1 110.2(3) . . ?
C12 N1 Bi1 114.7(3) . . ?
C7 N1 Bi1 103.0(3) . . ?
C10 N2 C11 109.6(5) . . ?
C10 N2 C13 111.1(6) . . ?
C11 N2 C13 112.7(5) . . ?
C17 N3 C14 109.6(5) . . ?
C17 N3 C8 109.0(5) . . ?
C14 N3 C8 110.1(5) . . ?
C17 N3 Bi1 112.1(3) . . ?
C14 N3 Bi1 113.6(4) . . ?
C8 N3 Bi1 102.1(3) . . ?
C15 N4 C18 111.7(6) . . ?
C15 N4 C16 107.5(4) . . ?
C18 N4 C16 110.4(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
N3 Bi1 C1 C6 16.2(4) . . . . ?
N1 Bi1 C1 C6 -164.8(5) . . . . ?
Cl1 Bi1 C1 C6 113.9(4) . . . . ?
Cl2 Bi1 C1 C6 -67.3(4) . . . . ?
N3 Bi1 C1 C2 -166.2(5) . . . . ?
N1 Bi1 C1 C2 12.8(4) . . . . ?
Cl1 Bi1 C1 C2 -68.6(4) . . . . ?
Cl2 Bi1 C1 C2 110.2(4) . . . . ?
C6 C1 C2 C3 1.0(8) . . . . ?
Bi1 C1 C2 C3 -176.5(4) . . . . ?
C6 C1 C2 C7 -176.7(5) . . . . ?
Bi1 C1 C2 C7 5.8(7) . . . . ?
C1 C2 C3 C4 -2.4(9) . . . . ?
C7 C2 C3 C4 175.1(6) . . . . ?
C2 C3 C4 C5 2.3(11) . . . . ?
C3 C4 C5 C6 -0.6(11) . . . . ?
C4 C5 C6 C1 -0.9(10) . . . . ?
C4 C5 C6 C8 175.5(6) . . . . ?
C2 C1 C6 C5 0.7(9) . . . . ?
Bi1 C1 C6 C5 178.2(5) . . . . ?
C2 C1 C6 C8 -175.9(5) . . . . ?
Bi1 C1 C6 C8 1.6(7) . . . . ?
C3 C2 C7 N1 147.8(6) . . . . ?
C1 C2 C7 N1 -34.7(7) . . . . ?
C5 C6 C8 N3 150.3(6) . . . . ?
C1 C6 C8 N3 -33.2(8) . . . . ?
N1 C9 C10 N2 57.1(6) . . . . ?
N2 C11 C12 N1 -58.7(6) . . . . ?
N3 C14 C15 N4 -59.6(6) . . . . ?
N4 C16 C17 N3 57.9(6) . . . . ?
C10 C9 N1 C12 -55.1(6) . . . . ?
C10 C9 N1 C7 -175.3(5) . . . . ?
C10 C9 N1 Bi1 71.5(5) . . . . ?
C11 C12 N1 C9 55.5(6) . . . . ?
C11 C12 N1 C7 176.4(5) . . . . ?
C11 C12 N1 Bi1 -68.5(5) . . . . ?
C2 C7 N1 C9 -78.4(6) . . . . ?
C2 C7 N1 C12 161.7(5) . . . . ?
C2 C7 N1 Bi1 39.3(5) . . . . ?
C1 Bi1 N1 C9 90.0(4) . . . . ?
N3 Bi1 N1 C9 91.7(4) . . . . ?
Cl1 Bi1 N1 C9 -177.4(4) . . . . ?
Cl2 Bi1 N1 C9 5.4(4) . . . . ?
C1 Bi1 N1 C12 -146.6(4) . . . . ?
N3 Bi1 N1 C12 -145.0(4) . . . . ?
Cl1 Bi1 N1 C12 -54.0(3) . . . . ?
Cl2 Bi1 N1 C12 128.7(4) . . . . ?
C1 Bi1 N1 C7 -28.0(3) . . . . ?
N3 Bi1 N1 C7 -26.3(5) . . . . ?
Cl1 Bi1 N1 C7 64.6(3) . . . . ?
Cl2 Bi1 N1 C7 -112.6(3) . . . . ?
C9 C10 N2 C11 -57.5(6) . . . . ?
C9 C10 N2 C13 177.2(5) . . . . ?
C12 C11 N2 C10 59.0(6) . . . . ?
C12 C11 N2 C13 -176.6(5) . . . . ?
C16 C17 N3 C14 -52.7(6) . . . . ?
C16 C17 N3 C8 -173.3(5) . . . . ?
C16 C17 N3 Bi1 74.5(5) . . . . ?
C15 C14 N3 C17 53.2(6) . . . . ?
C15 C14 N3 C8 173.1(5) . . . . ?
C15 C14 N3 Bi1 -73.2(5) . . . . ?
C6 C8 N3 C17 -78.0(6) . . . . ?
C6 C8 N3 C14 161.7(5) . . . . ?
C6 C8 N3 Bi1 40.7(5) . . . . ?
C1 Bi1 N3 C17 86.4(4) . . . . ?
N1 Bi1 N3 C17 84.8(4) . . . . ?
Cl1 Bi1 N3 C17 -1.3(4) . . . . ?
Cl2 Bi1 N3 C17 175.2(4) . . . . ?
C1 Bi1 N3 C14 -148.6(4) . . . . ?
N1 Bi1 N3 C14 -150.3(4) . . . . ?
Cl1 Bi1 N3 C14 123.7(4) . . . . ?
Cl2 Bi1 N3 C14 -59.8(4) . . . . ?
C1 Bi1 N3 C8 -30.1(3) . . . . ?
N1 Bi1 N3 C8 -31.7(5) . . . . ?
Cl1 Bi1 N3 C8 -117.8(3) . . . . ?
Cl2 Bi1 N3 C8 58.7(3) . . . . ?
C14 C15 N4 C18 -176.5(5) . . . . ?
C14 C15 N4 C16 62.3(6) . . . . ?
C17 C16 N4 C15 -61.1(6) . . . . ?
C17 C16 N4 C18 176.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.360
_refine_diff_density_min         -1.991
_refine_diff_density_rms         0.130

#===END

data_682012
_database_code_depnum_ccdc_archive 'CCDC 682012'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H29 Bi Br2 N4'
_chemical_formula_sum            'C18 H29 Bi Br2 N4'
_chemical_formula_weight         670.25

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'
Br Br -0.2901 2.4595 '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 '
_symmetry_space_group_name_Hall  '-P 2yn'

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                   8.5566(7)
_cell_length_b                   14.8965(12)
_cell_length_c                   17.7934(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.2550(10)
_cell_angle_gamma                90.00
_cell_volume                     2216.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4219
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.009
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272
_exptl_absorpt_coefficient_mu    11.569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.081
_exptl_absorpt_correction_T_max  0.2042
_exptl_absorpt_process_details   'Bruker, 2001.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(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            15790
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3903
_reflns_number_gt                3551
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0234P)^2^+4.8455P] 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         3903
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.001

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 0.36867(3) 0.277323(17) 0.259688(13) 0.02810(9) Uani 1 1 d . . .
Br2 Br 0.66996(9) 0.33892(6) 0.33996(4) 0.0502(2) Uani 1 1 d . . .
Br1 Br 0.07300(9) 0.20661(6) 0.17786(5) 0.0540(2) Uani 1 1 d . . .
C1 C 0.4415(7) 0.1387(4) 0.2886(4) 0.0294(14) Uani 1 1 d . . .
C2 C 0.3656(8) 0.0920(5) 0.3379(4) 0.0382(16) Uani 1 1 d . . .
C3 C 0.4112(10) 0.0032(5) 0.3549(5) 0.056(2) Uani 1 1 d . . .
H3 H 0.3642 -0.0292 0.3890 0.067 Uiso 1 1 calc R . .
C4 C 0.5247(10) -0.0371(6) 0.3219(5) 0.063(2) Uani 1 1 d . . .
H4 H 0.5518 -0.0969 0.3328 0.075 Uiso 1 1 calc R . .
C5 C 0.5981(9) 0.0098(5) 0.2730(5) 0.051(2) Uani 1 1 d . . .
H5 H 0.6748 -0.0182 0.2511 0.061 Uiso 1 1 calc R . .
C6 C 0.5583(8) 0.0996(5) 0.2559(4) 0.0363(16) Uani 1 1 d . . .
C7 C 0.2329(9) 0.1357(5) 0.3669(4) 0.0413(17) Uani 1 1 d . . .
H7A H 0.1328 0.1254 0.3305 0.050 Uiso 1 1 calc R . .
H7B H 0.2246 0.1082 0.4154 0.050 Uiso 1 1 calc R . .
C12 C 0.1049(8) 0.2785(5) 0.3816(4) 0.0458(19) Uani 1 1 d . . .
H12A H 0.0569 0.2485 0.4195 0.055 Uiso 1 1 calc R . .
H12B H 0.0320 0.2729 0.3320 0.055 Uiso 1 1 calc R . .
C11 C 0.1279(8) 0.3763(5) 0.4022(4) 0.0453(19) Uani 1 1 d . . .
H11A H 0.1707 0.4074 0.3631 0.054 Uiso 1 1 calc R . .
H11B H 0.0257 0.4033 0.4043 0.054 Uiso 1 1 calc R . .
C10 C 0.3904(8) 0.3482(5) 0.4701(4) 0.0416(18) Uani 1 1 d . . .
H10A H 0.4660 0.3562 0.5186 0.050 Uiso 1 1 calc R . .
H10B H 0.4309 0.3801 0.4306 0.050 Uiso 1 1 calc R . .
C9 C 0.3764(9) 0.2504(5) 0.4505(4) 0.0396(17) Uani 1 1 d . . .
H9A H 0.4799 0.2278 0.4454 0.047 Uiso 1 1 calc R . .
H9B H 0.3448 0.2179 0.4921 0.047 Uiso 1 1 calc R . .
C13 C 0.2545(10) 0.4776(6) 0.5003(5) 0.063(2) Uani 1 1 d . . .
H13A H 0.2929 0.5124 0.4625 0.095 Uiso 1 1 calc R . .
H13B H 0.3297 0.4813 0.5487 0.095 Uiso 1 1 calc R . .
H13C H 0.1530 0.5006 0.5061 0.095 Uiso 1 1 calc R . .
C8 C 0.6415(8) 0.1557(5) 0.2068(4) 0.0424(18) Uani 1 1 d . . .
H8A H 0.7330 0.1847 0.2392 0.051 Uiso 1 1 calc R . .
H8B H 0.6807 0.1170 0.1710 0.051 Uiso 1 1 calc R . .
C17 C 0.4301(8) 0.1850(5) 0.0940(4) 0.0399(17) Uani 1 1 d . . .
H17A H 0.3593 0.1418 0.1102 0.048 Uiso 1 1 calc R . .
H17B H 0.4948 0.1534 0.0639 0.048 Uiso 1 1 calc R . .
C16 C 0.3326(9) 0.2550(5) 0.0450(4) 0.0439(19) Uani 1 1 d . . .
H16A H 0.2673 0.2268 0.0000 0.053 Uiso 1 1 calc R . .
H16B H 0.2617 0.2835 0.0737 0.053 Uiso 1 1 calc R . .
C15 C 0.5330(9) 0.3634(5) 0.0881(4) 0.0475(19) Uani 1 1 d . . .
H15A H 0.4659 0.3930 0.1181 0.057 Uiso 1 1 calc R . .
H15B H 0.6005 0.4085 0.0718 0.057 Uiso 1 1 calc R . .
C14 C 0.6361(8) 0.2947(5) 0.1371(4) 0.0401(17) Uani 1 1 d . . .
H14A H 0.7066 0.2669 0.1078 0.048 Uiso 1 1 calc R . .
H14B H 0.7017 0.3240 0.1815 0.048 Uiso 1 1 calc R . .
C18 C 0.3409(11) 0.3872(6) -0.0296(5) 0.064(2) Uani 1 1 d . . .
H18A H 0.2698 0.3567 -0.0707 0.096 Uiso 1 1 calc R . .
H18B H 0.4115 0.4252 -0.0506 0.096 Uiso 1 1 calc R . .
H18C H 0.2797 0.4229 -0.0014 0.096 Uiso 1 1 calc R . .
N1 N 0.2583(6) 0.2339(4) 0.3784(3) 0.0337(13) Uani 1 1 d . . .
N2 N 0.2368(7) 0.3854(4) 0.4759(3) 0.0426(15) Uani 1 1 d . . .
N3 N 0.5363(6) 0.2250(4) 0.1631(3) 0.0348(13) Uani 1 1 d . . .
N4 N 0.4333(7) 0.3221(4) 0.0211(3) 0.0441(15) 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 0.02466(14) 0.03204(15) 0.02766(14) -0.00123(11) 0.00569(10) 0.00006(10)
Br2 0.0385(4) 0.0691(6) 0.0426(4) -0.0069(4) 0.0076(3) -0.0131(4)
Br1 0.0359(4) 0.0755(6) 0.0483(5) -0.0137(4) 0.0036(3) -0.0077(4)
C1 0.027(3) 0.026(4) 0.032(4) 0.007(3) 0.000(3) 0.008(3)
C2 0.044(4) 0.034(4) 0.038(4) 0.004(3) 0.011(3) -0.005(3)
C3 0.064(5) 0.039(5) 0.067(6) 0.001(4) 0.021(4) -0.016(4)
C4 0.068(6) 0.036(5) 0.086(7) 0.015(5) 0.022(5) 0.009(4)
C5 0.049(5) 0.046(5) 0.056(5) -0.008(4) 0.005(4) 0.016(4)
C6 0.037(4) 0.040(4) 0.031(4) -0.004(3) 0.005(3) -0.002(3)
C7 0.047(4) 0.036(4) 0.045(4) -0.001(3) 0.020(3) -0.010(3)
C12 0.029(4) 0.067(6) 0.045(4) -0.006(4) 0.015(3) 0.005(4)
C11 0.032(4) 0.053(5) 0.052(5) -0.001(4) 0.013(3) 0.012(3)
C10 0.036(4) 0.056(5) 0.033(4) -0.001(4) 0.007(3) -0.002(4)
C9 0.046(4) 0.047(4) 0.025(4) 0.003(3) 0.006(3) 0.005(3)
C13 0.062(6) 0.055(6) 0.076(6) -0.017(5) 0.020(5) 0.003(4)
C8 0.033(4) 0.053(5) 0.044(4) 0.000(4) 0.015(3) 0.015(3)
C17 0.044(4) 0.045(4) 0.031(4) -0.011(3) 0.009(3) -0.004(3)
C16 0.041(4) 0.058(5) 0.032(4) -0.010(4) 0.006(3) 0.004(4)
C15 0.052(5) 0.047(5) 0.048(5) -0.001(4) 0.022(4) -0.006(4)
C14 0.032(4) 0.051(5) 0.040(4) -0.001(4) 0.014(3) -0.001(3)
C18 0.077(6) 0.061(6) 0.053(5) 0.011(5) 0.012(5) 0.016(5)
N1 0.027(3) 0.047(4) 0.029(3) 0.000(3) 0.008(2) -0.002(3)
N2 0.042(3) 0.050(4) 0.037(3) -0.012(3) 0.011(3) 0.001(3)
N3 0.034(3) 0.036(3) 0.035(3) -0.003(3) 0.006(2) -0.003(3)
N4 0.053(4) 0.049(4) 0.033(3) 0.005(3) 0.014(3) 0.005(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 C1 2.187(6) . ?
Bi1 N1 2.572(5) . ?
Bi1 N3 2.583(5) . ?
Bi1 Br2 2.8222(8) . ?
Bi1 Br1 2.8401(8) . ?
C1 C2 1.383(9) . ?
C1 C6 1.387(9) . ?
C2 C3 1.394(10) . ?
C2 C7 1.493(9) . ?
C3 C4 1.375(11) . ?
C4 C5 1.367(11) . ?
C5 C6 1.399(10) . ?
C6 C8 1.494(10) . ?
C7 N1 1.487(9) . ?
C12 N1 1.483(8) . ?
C12 C11 1.506(10) . ?
C11 N2 1.445(9) . ?
C10 N2 1.451(8) . ?
C10 C9 1.496(10) . ?
C9 N1 1.476(8) . ?
C13 N2 1.438(10) . ?
C8 N3 1.478(9) . ?
C17 N3 1.489(8) . ?
C17 C16 1.495(10) . ?
C16 N4 1.441(9) . ?
C15 N4 1.447(9) . ?
C15 C14 1.503(10) . ?
C14 N3 1.480(8) . ?
C18 N4 1.441(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Bi1 N1 72.8(2) . . ?
C1 Bi1 N3 72.6(2) . . ?
N1 Bi1 N3 145.40(18) . . ?
C1 Bi1 Br2 90.22(16) . . ?
N1 Bi1 Br2 96.97(12) . . ?
N3 Bi1 Br2 81.85(12) . . ?
C1 Bi1 Br1 87.06(16) . . ?
N1 Bi1 Br1 83.41(12) . . ?
N3 Bi1 Br1 96.13(12) . . ?
Br2 Bi1 Br1 177.01(3) . . ?
C2 C1 C6 122.1(6) . . ?
C2 C1 Bi1 118.4(5) . . ?
C6 C1 Bi1 119.5(5) . . ?
C1 C2 C3 117.9(7) . . ?
C1 C2 C7 119.6(6) . . ?
C3 C2 C7 122.4(7) . . ?
C4 C3 C2 120.8(8) . . ?
C5 C4 C3 120.7(8) . . ?
C4 C5 C6 120.2(7) . . ?
C1 C6 C5 118.3(7) . . ?
C1 C6 C8 119.1(6) . . ?
C5 C6 C8 122.5(7) . . ?
N1 C7 C2 112.1(5) . . ?
N1 C12 C11 111.8(6) . . ?
N2 C11 C12 109.7(6) . . ?
N2 C10 C9 111.1(6) . . ?
N1 C9 C10 111.8(6) . . ?
N3 C8 C6 112.7(5) . . ?
N3 C17 C16 111.7(6) . . ?
N4 C16 C17 111.2(6) . . ?
N4 C15 C14 111.1(6) . . ?
N3 C14 C15 110.7(6) . . ?
C9 N1 C12 109.9(5) . . ?
C9 N1 C7 109.7(6) . . ?
C12 N1 C7 109.9(5) . . ?
C9 N1 Bi1 111.7(4) . . ?
C12 N1 Bi1 113.6(4) . . ?
C7 N1 Bi1 101.8(4) . . ?
C13 N2 C11 111.7(6) . . ?
C13 N2 C10 110.3(6) . . ?
C11 N2 C10 108.6(5) . . ?
C8 N3 C14 109.1(5) . . ?
C8 N3 C17 110.6(6) . . ?
C14 N3 C17 108.3(5) . . ?
C8 N3 Bi1 102.9(4) . . ?
C14 N3 Bi1 115.8(4) . . ?
C17 N3 Bi1 110.0(4) . . ?
C18 N4 C16 111.6(6) . . ?
C18 N4 C15 112.3(7) . . ?
C16 N4 C15 109.7(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
N1 Bi1 C1 C2 15.7(5) . . . . ?
N3 Bi1 C1 C2 -165.7(6) . . . . ?
Br2 Bi1 C1 C2 112.9(5) . . . . ?
Br1 Bi1 C1 C2 -68.3(5) . . . . ?
N1 Bi1 C1 C6 -166.0(6) . . . . ?
N3 Bi1 C1 C6 12.6(5) . . . . ?
Br2 Bi1 C1 C6 -68.8(5) . . . . ?
Br1 Bi1 C1 C6 110.0(5) . . . . ?
C6 C1 C2 C3 0.6(10) . . . . ?
Bi1 C1 C2 C3 178.9(5) . . . . ?
C6 C1 C2 C7 -175.7(6) . . . . ?
Bi1 C1 C2 C7 2.6(9) . . . . ?
C1 C2 C3 C4 -1.8(12) . . . . ?
C7 C2 C3 C4 174.4(8) . . . . ?
C2 C3 C4 C5 1.6(14) . . . . ?
C3 C4 C5 C6 -0.1(13) . . . . ?
C2 C1 C6 C5 0.8(10) . . . . ?
Bi1 C1 C6 C5 -177.5(5) . . . . ?
C2 C1 C6 C8 -176.6(6) . . . . ?
Bi1 C1 C6 C8 5.1(8) . . . . ?
C4 C5 C6 C1 -1.1(11) . . . . ?
C4 C5 C6 C8 176.2(7) . . . . ?
C1 C2 C7 N1 -33.9(9) . . . . ?
C3 C2 C7 N1 149.8(7) . . . . ?
N1 C12 C11 N2 -58.7(8) . . . . ?
N2 C10 C9 N1 57.1(8) . . . . ?
C1 C6 C8 N3 -33.5(9) . . . . ?
C5 C6 C8 N3 149.3(7) . . . . ?
N3 C17 C16 N4 57.5(8) . . . . ?
N4 C15 C14 N3 -59.2(8) . . . . ?
C10 C9 N1 C12 -51.6(8) . . . . ?
C10 C9 N1 C7 -172.5(5) . . . . ?
C10 C9 N1 Bi1 75.5(6) . . . . ?
C11 C12 N1 C9 52.7(8) . . . . ?
C11 C12 N1 C7 173.5(6) . . . . ?
C11 C12 N1 Bi1 -73.2(7) . . . . ?
C2 C7 N1 C9 -77.9(7) . . . . ?
C2 C7 N1 C12 161.2(6) . . . . ?
C2 C7 N1 Bi1 40.5(6) . . . . ?
C1 Bi1 N1 C9 87.0(5) . . . . ?
N3 Bi1 N1 C9 84.7(5) . . . . ?
Br2 Bi1 N1 C9 -1.1(4) . . . . ?
Br1 Bi1 N1 C9 175.9(4) . . . . ?
C1 Bi1 N1 C12 -148.0(5) . . . . ?
N3 Bi1 N1 C12 -150.4(4) . . . . ?
Br2 Bi1 N1 C12 123.9(4) . . . . ?
Br1 Bi1 N1 C12 -59.1(4) . . . . ?
C1 Bi1 N1 C7 -29.9(4) . . . . ?
N3 Bi1 N1 C7 -32.2(5) . . . . ?
Br2 Bi1 N1 C7 -118.0(4) . . . . ?
Br1 Bi1 N1 C7 59.0(4) . . . . ?
C12 C11 N2 C13 -176.3(6) . . . . ?
C12 C11 N2 C10 61.8(7) . . . . ?
C9 C10 N2 C13 175.7(6) . . . . ?
C9 C10 N2 C11 -61.6(8) . . . . ?
C6 C8 N3 C14 161.5(6) . . . . ?
C6 C8 N3 C17 -79.4(7) . . . . ?
C6 C8 N3 Bi1 38.1(6) . . . . ?
C15 C14 N3 C8 176.4(6) . . . . ?
C15 C14 N3 C17 55.9(7) . . . . ?
C15 C14 N3 Bi1 -68.2(6) . . . . ?
C16 C17 N3 C8 -175.0(6) . . . . ?
C16 C17 N3 C14 -55.4(7) . . . . ?
C16 C17 N3 Bi1 72.0(6) . . . . ?
C1 Bi1 N3 C8 -27.1(4) . . . . ?
N1 Bi1 N3 C8 -24.7(5) . . . . ?
Br2 Bi1 N3 C8 65.7(4) . . . . ?
Br1 Bi1 N3 C8 -112.0(4) . . . . ?
C1 Bi1 N3 C14 -146.0(5) . . . . ?
N1 Bi1 N3 C14 -143.7(4) . . . . ?
Br2 Bi1 N3 C14 -53.2(4) . . . . ?
Br1 Bi1 N3 C14 129.1(4) . . . . ?
C1 Bi1 N3 C17 90.8(5) . . . . ?
N1 Bi1 N3 C17 93.1(5) . . . . ?
Br2 Bi1 N3 C17 -176.4(4) . . . . ?
Br1 Bi1 N3 C17 5.8(4) . . . . ?
C17 C16 N4 C18 176.8(6) . . . . ?
C17 C16 N4 C15 -58.1(8) . . . . ?
C14 C15 N4 C18 -176.1(6) . . . . ?
C14 C15 N4 C16 59.2(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.732
_refine_diff_density_min         -1.664
_refine_diff_density_rms         0.141

#===END

data_682013
_database_code_depnum_ccdc_archive 'CCDC 682013'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H29 Bi I2 N4'
_chemical_formula_weight         764.23

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'
I I -0.4742 1.8119 '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   'C2/c '

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

_cell_length_a                   17.939(2)
_cell_length_b                   13.7513(16)
_cell_length_c                   9.4025(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.319(2)
_cell_angle_gamma                90.00
_cell_volume                     2312.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3598
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1416
_exptl_absorpt_coefficient_mu    10.301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.109
_exptl_absorpt_correction_T_max  0.130
_exptl_absorpt_process_details   'Bruker, 2001.'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      297(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            9106
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2362
_reflns_number_gt                2279
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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^)+(0.0165P)^2^+9.6075P] 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         2362
_refine_ls_number_parameters     116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_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 0.5000 0.695496(18) 0.2500 0.03009(9) Uani 1 2 d S . .
C1 C 0.5000 0.8565(5) 0.2500 0.0332(16) Uani 1 2 d S . .
C2 C 0.5463(3) 0.9041(4) 0.1606(7) 0.0449(14) Uani 1 1 d . . .
C3 C 0.5450(4) 1.0057(4) 0.1638(7) 0.0525(17) Uani 1 1 d . . .
H3 H 0.5754 1.0405 0.1061 0.063 Uiso 1 1 calc R . .
C4 C 0.5000 1.0548(6) 0.2500 0.058(3) Uani 1 2 d S . .
H4 H 0.5000 1.1224 0.2500 0.069 Uiso 1 2 calc SR . .
C5 C 0.5880(3) 0.8470(4) 0.0567(7) 0.0490(15) Uani 1 1 d . . .
H5A H 0.5565 0.8401 -0.0313 0.059 Uiso 1 1 calc R . .
H5B H 0.6320 0.8835 0.0351 0.059 Uiso 1 1 calc R . .
C6 C 0.6236(3) 0.6882(5) -0.0183(6) 0.0481(15) Uani 1 1 d . . .
H6A H 0.6579 0.7210 -0.0773 0.058 Uiso 1 1 calc R . .
H6B H 0.5764 0.6798 -0.0746 0.058 Uiso 1 1 calc R . .
C7 C 0.6547(3) 0.5902(5) 0.0242(7) 0.0506(15) Uani 1 1 d . . .
H7A H 0.6198 0.5561 0.0802 0.061 Uiso 1 1 calc R . .
H7B H 0.6615 0.5519 -0.0606 0.061 Uiso 1 1 calc R . .
C8 C 0.7136(3) 0.6557(4) 0.2352(7) 0.0464(14) Uani 1 1 d . . .
H8A H 0.7604 0.6624 0.2931 0.056 Uiso 1 1 calc R . .
H8B H 0.6789 0.6205 0.2906 0.056 Uiso 1 1 calc R . .
C9 C 0.6823(3) 0.7553(4) 0.1985(6) 0.0418(13) Uani 1 1 d . . .
H9A H 0.6736 0.7897 0.2858 0.050 Uiso 1 1 calc R . .
H9B H 0.7186 0.7920 0.1490 0.050 Uiso 1 1 calc R . .
C10 C 0.7579(4) 0.5061(5) 0.1429(8) 0.0670(19) Uani 1 1 d . . .
H10A H 0.8059 0.5142 0.1939 0.100 Uiso 1 1 calc R . .
H10B H 0.7635 0.4701 0.0569 0.100 Uiso 1 1 calc R . .
H10C H 0.7253 0.4714 0.2015 0.100 Uiso 1 1 calc R . .
I1 I 0.59018(2) 0.70509(3) 0.54332(4) 0.05675(14) Uani 1 1 d . . .
N1 N 0.6115(2) 0.7493(3) 0.1076(5) 0.0371(10) Uani 1 1 d . . .
N2 N 0.7262(3) 0.6008(4) 0.1074(5) 0.0463(12) 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 0.03111(15) 0.02852(14) 0.03087(15) 0.000 0.00395(10) 0.000
C1 0.040(4) 0.022(3) 0.037(4) 0.000 -0.004(3) 0.000
C2 0.040(3) 0.036(3) 0.056(4) 0.013(3) -0.014(3) -0.002(2)
C3 0.062(4) 0.038(3) 0.054(4) 0.015(3) -0.023(3) -0.014(3)
C4 0.078(7) 0.028(4) 0.061(6) 0.000 -0.032(5) 0.000
C5 0.044(3) 0.048(3) 0.055(4) 0.022(3) 0.008(3) -0.002(3)
C6 0.039(3) 0.071(4) 0.035(3) 0.002(3) 0.007(2) 0.002(3)
C7 0.044(3) 0.062(4) 0.048(4) -0.013(3) 0.012(3) 0.001(3)
C8 0.034(3) 0.053(3) 0.051(4) 0.007(3) -0.004(3) 0.000(3)
C9 0.029(3) 0.048(3) 0.048(3) 0.006(3) 0.005(2) -0.006(2)
C10 0.058(4) 0.065(4) 0.079(5) 0.002(4) 0.013(4) 0.014(4)
I1 0.0530(3) 0.0709(3) 0.0456(3) -0.00217(19) -0.0012(2) 0.0115(2)
N1 0.031(2) 0.043(3) 0.038(3) 0.009(2) 0.0075(19) 0.0026(19)
N2 0.037(3) 0.051(3) 0.052(3) 0.003(2) 0.010(2) 0.007(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
Bi1 C1 2.214(7) . ?
Bi1 N1 2.596(4) . ?
Bi1 N1 2.596(4) 2_655 ?
Bi1 I1 3.0934(5) . ?
Bi1 I1 3.0934(5) 2_655 ?
C1 C2 1.389(7) 2_655 ?
C1 C2 1.389(7) . ?
C2 C3 1.397(7) . ?
C2 C5 1.497(9) . ?
C3 C4 1.365(8) . ?
C3 H3 0.9300 . ?
C4 C3 1.365(8) 2_655 ?
C4 H4 0.9300 . ?
C5 N1 1.477(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.482(7) . ?
C6 C7 1.502(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N2 1.457(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.451(8) . ?
C8 C9 1.510(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.479(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.450(8) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C1 Bi1 N1 73.43(10) . . ?
C1 Bi1 N1 73.43(10) . 2_655 ?
N1 Bi1 N1 146.9(2) . 2_655 ?
C1 Bi1 I1 87.555(9) . . ?
N1 Bi1 I1 94.36(10) . . ?
N1 Bi1 I1 84.24(10) 2_655 . ?
C1 Bi1 I1 87.555(9) . 2_655 ?
N1 Bi1 I1 84.24(10) . 2_655 ?
N1 Bi1 I1 94.36(10) 2_655 2_655 ?
I1 Bi1 I1 175.111(19) . 2_655 ?
C2 C1 C2 123.8(7) 2_655 . ?
C2 C1 Bi1 118.1(3) 2_655 . ?
C2 C1 Bi1 118.1(3) . . ?
C1 C2 C3 116.5(6) . . ?
C1 C2 C5 119.9(5) . . ?
C3 C2 C5 123.2(6) . . ?
C4 C3 C2 121.2(6) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C3 120.7(8) . 2_655 ?
C3 C4 H4 119.7 . . ?
C3 C4 H4 119.7 2_655 . ?
N1 C5 C2 114.2(5) . . ?
N1 C5 H5A 108.7 . . ?
C2 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
C2 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
N1 C6 C7 111.7(5) . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C6 110.3(5) . . ?
N2 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N2 C8 C9 111.2(5) . . ?
N2 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 C8 111.7(5) . . ?
N1 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 N1 C9 110.4(4) . . ?
C5 N1 C6 108.2(4) . . ?
C9 N1 C6 108.8(4) . . ?
C5 N1 Bi1 102.4(3) . . ?
C9 N1 Bi1 112.3(3) . . ?
C6 N1 Bi1 114.5(3) . . ?
C10 N2 C8 111.0(5) . . ?
C10 N2 C7 110.4(5) . . ?
C8 N2 C7 108.1(4) . . ?

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
N1 Bi1 C1 C2 -169.3(3) . . . 2_655 ?
N1 Bi1 C1 C2 10.7(3) 2_655 . . 2_655 ?
I1 Bi1 C1 C2 -74.0(3) . . . 2_655 ?
I1 Bi1 C1 C2 106.0(3) 2_655 . . 2_655 ?
N1 Bi1 C1 C2 10.7(3) . . . . ?
N1 Bi1 C1 C2 -169.3(3) 2_655 . . . ?
I1 Bi1 C1 C2 106.0(3) . . . . ?
I1 Bi1 C1 C2 -74.0(3) 2_655 . . . ?
C2 C1 C2 C3 0.2(4) 2_655 . . . ?
Bi1 C1 C2 C3 -179.8(4) . . . . ?
C2 C1 C2 C5 -173.4(6) 2_655 . . . ?
Bi1 C1 C2 C5 6.6(6) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C5 C2 C3 C4 173.0(5) . . . . ?
C2 C3 C4 C3 0.2(4) . . . 2_655 ?
C1 C2 C5 N1 -33.4(7) . . . . ?
C3 C2 C5 N1 153.4(5) . . . . ?
N1 C6 C7 N2 -59.7(6) . . . . ?
N2 C8 C9 N1 57.9(6) . . . . ?
C2 C5 N1 C9 -83.3(6) . . . . ?
C2 C5 N1 C6 157.7(5) . . . . ?
C2 C5 N1 Bi1 36.4(5) . . . . ?
C8 C9 N1 C5 -171.9(5) . . . . ?
C8 C9 N1 C6 -53.3(6) . . . . ?
C8 C9 N1 Bi1 74.5(5) . . . . ?
C7 C6 N1 C5 174.5(5) . . . . ?
C7 C6 N1 C9 54.6(6) . . . . ?
C7 C6 N1 Bi1 -72.0(5) . . . . ?
C1 Bi1 N1 C5 -25.0(3) . . . . ?
N1 Bi1 N1 C5 -25.0(3) 2_655 . . . ?
I1 Bi1 N1 C5 -111.2(3) . . . . ?
I1 Bi1 N1 C5 64.1(3) 2_655 . . . ?
C1 Bi1 N1 C9 93.4(3) . . . . ?
N1 Bi1 N1 C9 93.4(3) 2_655 . . . ?
I1 Bi1 N1 C9 7.3(3) . . . . ?
I1 Bi1 N1 C9 -177.4(3) 2_655 . . . ?
C1 Bi1 N1 C6 -141.8(4) . . . . ?
N1 Bi1 N1 C6 -141.8(4) 2_655 . . . ?
I1 Bi1 N1 C6 132.0(3) . . . . ?
I1 Bi1 N1 C6 -52.7(3) 2_655 . . . ?
C9 C8 N2 C10 178.6(5) . . . . ?
C9 C8 N2 C7 -60.2(6) . . . . ?
C6 C7 N2 C10 -177.4(5) . . . . ?
C6 C7 N2 C8 60.9(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.891
_refine_diff_density_min         -1.918
_refine_diff_density_rms         0.124