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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
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#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_cg_010x

_database_code_CSD               ?
_database_code_depnum_ccdc_archive 'CCDC 1011105'

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H56 Bi In N2'
_chemical_formula_sum            'C35 H56 Bi In N2'
_chemical_formula_weight         828.61

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'
In In -0.7276 1.3100 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7410(4)
_cell_length_b                   21.4064(10)
_cell_length_c                   19.0397(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.2600(10)
_cell_angle_gamma                90
_cell_volume                     3516.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    64276
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      31.62

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.227
_exptl_absorpt_coefficient_mu    5.677
_shelx_estimated_absorpt_T_min   0.261
_shelx_estimated_absorpt_T_max   0.359
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_T_max  0.50
_exptl_absorpt_process_details   
; 
 BRUKER AXS SMART APEX 2 Vers. 3.0-2009
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-RAY tube'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_measurement_device_type  
; 
 Bruker D8 KAPPA series II with APEX II area detector system
;
_diffrn_measurement_method       
;
 Data collection strategy APEX 2/COSMO
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            127401
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.903
_diffrn_reflns_theta_max         31.708
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             11625
_reflns_number_gt                10388
_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       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_cell_refinement       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_data_reduction        'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_structure_solution    'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_structure_refinement  'BRUKER AXS Inc. 2013 Vers. 2013/4'
_computing_molecular_graphics    'BRUKER AXS Inc. 2008 Vers. 2008/4'
_computing_publication_material  'BRUKER AXS Inc. 2013 Vers. 2013/4'

_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
 The methyl groups are idealized with
 tetrahedral angles in a combined 
 rotating and rigid group refinement
 with the 1.5 fold isotropic displacement
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0197P)²+7.5304P] 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         11625
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0631
_refine_ls_wR_factor_gt          0.0603
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Bi1 Bi -0.09485(2) 0.22775(2) 0.95136(2) 0.01932(3) Uani 1 1 d . . . . .
In1 In 0.18769(2) 0.23248(2) 0.89449(2) 0.01194(4) Uani 1 1 d . . . . .
N1 N 0.1746(2) 0.16597(8) 0.80482(11) 0.0128(4) Uani 1 1 d . . . . .
N2 N 0.1659(2) 0.30749(9) 0.81375(11) 0.0132(4) Uani 1 1 d . . . . .
C1 C 0.2372(3) 0.18076(10) 0.74793(13) 0.0131(4) Uani 1 1 d . . . . .
C2 C 0.2750(3) 0.24203(10) 0.72988(14) 0.0148(4) Uani 1 1 d . . . . .
H2 H 0.3423 0.2449 0.6955 0.018 Uiso 1 1 d R U . . .
C3 C 0.2283(3) 0.29974(10) 0.75515(13) 0.0126(4) Uani 1 1 d . . . . .
C4 C 0.2705(3) 0.12972(11) 0.69726(14) 0.0192(5) Uani 1 1 d . . . . .
H4A H 0.3441 0.0998 0.7228 0.029 Uiso 1 1 calc R U . . .
H4B H 0.3151 0.1483 0.6581 0.029 Uiso 1 1 calc R U . . .
H4C H 0.1738 0.1081 0.6782 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2508(3) 0.35622(11) 0.70990(15) 0.0197(5) Uani 1 1 d . . . . .
H5A H 0.1500 0.3754 0.6926 0.030 Uiso 1 1 calc R U . . .
H5B H 0.2992 0.3432 0.6693 0.030 Uiso 1 1 calc R U . . .
H5C H 0.3178 0.3866 0.7386 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1132(3) 0.10424(10) 0.81122(13) 0.0132(4) Uani 1 1 d . . . . .
C7 C -0.0450(3) 0.09383(11) 0.78608(14) 0.0166(4) Uani 1 1 d . . . . .
C8 C -0.1064(3) 0.03470(11) 0.79525(15) 0.0199(5) Uani 1 1 d . . . . .
H8 H -0.2127 0.0269 0.7779 0.024 Uiso 1 1 d R U . . .
C9 C -0.0149(3) -0.01265(11) 0.82908(15) 0.0206(5) Uani 1 1 d . . . . .
H9 H -0.0587 -0.0525 0.8353 0.025 Uiso 1 1 d R U . . .
C10 C 0.1400(3) -0.00174(11) 0.85371(15) 0.0186(5) Uani 1 1 d . . . . .
H10 H 0.2021 -0.0344 0.8769 0.022 Uiso 1 1 d R U . . .
C11 C 0.2072(3) 0.05639(10) 0.84532(13) 0.0149(4) Uani 1 1 d . . . . .
C12 C -0.1473(3) 0.14426(12) 0.74735(18) 0.0268(6) Uani 1 1 d . . . . .
H12 H -0.0990 0.1856 0.7618 0.032 Uiso 1 1 d R U . . .
C13 C -0.1555(4) 0.1379(2) 0.6664(2) 0.0472(10) Uani 1 1 d . . . . .
H13A H -0.0516 0.1430 0.6541 0.071 Uiso 1 1 calc R U . . .
H13B H -0.2244 0.1701 0.6423 0.071 Uiso 1 1 calc R U . . .
H13C H -0.1958 0.0965 0.6512 0.071 Uiso 1 1 calc R U . . .
C14 C -0.3113(3) 0.14426(15) 0.7659(2) 0.0342(7) Uani 1 1 d . . . . .
H14A H -0.3633 0.1050 0.7499 0.051 Uiso 1 1 calc R U . . .
H14B H -0.3700 0.1795 0.7422 0.051 Uiso 1 1 calc R U . . .
H14C H -0.3056 0.1483 0.8176 0.051 Uiso 1 1 calc R U . . .
C15 C 0.3765(3) 0.06674(11) 0.87632(15) 0.0182(5) Uani 1 1 d . . . . .
H15 H 0.4098 0.1073 0.8576 0.022 Uiso 1 1 d R U . . .
C16 C 0.4822(3) 0.01496(13) 0.85510(18) 0.0257(6) Uani 1 1 d . . . . .
H16A H 0.4574 -0.0247 0.8764 0.039 Uiso 1 1 calc R U . . .
H16B H 0.5908 0.0257 0.8722 0.039 Uiso 1 1 calc R U . . .
H16C H 0.4659 0.0109 0.8032 0.039 Uiso 1 1 calc R U . . .
C17 C 0.3941(3) 0.07191(13) 0.95747(16) 0.0249(6) Uani 1 1 d . . . . .
H17A H 0.3260 0.1050 0.9701 0.037 Uiso 1 1 calc R U . . .
H17B H 0.5019 0.0819 0.9770 0.037 Uiso 1 1 calc R U . . .
H17C H 0.3656 0.0321 0.9772 0.037 Uiso 1 1 calc R U . . .
C18 C 0.0997(3) 0.36692(10) 0.82794(14) 0.0147(4) Uani 1 1 d . . . . .
C19 C 0.1923(3) 0.41435(11) 0.86456(14) 0.0172(5) Uani 1 1 d . . . . .
C20 C 0.1206(3) 0.47064(11) 0.87812(16) 0.0228(5) Uani 1 1 d . . . . .
H20 H 0.1813 0.5031 0.9026 0.027 Uiso 1 1 d R U . . .
C21 C -0.0361(3) 0.47994(12) 0.85663(17) 0.0263(6) Uani 1 1 d . . . . .
H21 H -0.0821 0.5188 0.8654 0.032 Uiso 1 1 d R U . . .
C22 C -0.1260(3) 0.43256(12) 0.82219(16) 0.0224(5) Uani 1 1 d . . . . .
H22 H -0.2340 0.4391 0.8080 0.027 Uiso 1 1 d R U . . .
C23 C -0.0614(3) 0.37540(11) 0.80784(14) 0.0172(5) Uani 1 1 d . . . . .
C24 C 0.3633(3) 0.40591(11) 0.89218(15) 0.0194(5) Uani 1 1 d . . . . .
H24 H 0.3989 0.3671 0.8705 0.023 Uiso 1 1 d R U . . .
C25 C 0.3878(4) 0.39715(14) 0.97299(17) 0.0288(6) Uani 1 1 d . . . . .
H25A H 0.3562 0.4352 0.9955 0.043 Uiso 1 1 calc R U . . .
H25B H 0.4976 0.3888 0.9904 0.043 Uiso 1 1 calc R U . . .
H25C H 0.3254 0.3618 0.9849 0.043 Uiso 1 1 calc R U . . .
C26 C 0.4619(4) 0.46064(13) 0.87284(19) 0.0293(6) Uani 1 1 d . . . . .
H26A H 0.4447 0.4662 0.8211 0.044 Uiso 1 1 calc R U . . .
H26B H 0.5717 0.4518 0.8895 0.044 Uiso 1 1 calc R U . . .
H26C H 0.4323 0.4989 0.8956 0.044 Uiso 1 1 calc R U . . .
C27 C -0.1643(3) 0.32397(12) 0.77125(16) 0.0206(5) Uani 1 1 d . . . . .
H27A H -0.1176 0.2832 0.7891 0.025 Uiso 1 1 d R U . . .
C28 C -0.3292(3) 0.32610(14) 0.78906(19) 0.0292(6) Uani 1 1 d . . . . .
H28A H -0.3244 0.3301 0.8406 0.044 Uiso 1 1 calc R U . . .
H28B H -0.3840 0.2875 0.7727 0.044 Uiso 1 1 calc R U . . .
H28C H -0.3847 0.3620 0.7652 0.044 Uiso 1 1 calc R U . . .
C29 C -0.1701(4) 0.32481(17) 0.69096(19) 0.0350(7) Uani 1 1 d . . . . .
H29A H -0.1997 0.3666 0.6726 0.053 Uiso 1 1 calc R U . . .
H29B H -0.2466 0.2943 0.6689 0.053 Uiso 1 1 calc R U . . .
H29C H -0.0678 0.3141 0.6797 0.053 Uiso 1 1 calc R U . . .
C30 C -0.0202(5) 0.29940(16) 1.03897(18) 0.0372(8) Uani 1 1 d . . . . .
H30A H -0.0684 0.2887 1.0810 0.045 Uiso 1 1 d R U . . .
H30B H 0.0937 0.2973 1.0533 0.045 Uiso 1 1 d R U . . .
C31 C -0.0655(6) 0.36514(16) 1.0159(2) 0.0474(10) Uani 1 1 d . . . . .
H31A H -0.0133 0.3770 0.9760 0.071 Uiso 1 1 calc R U . . .
H31B H -0.0347 0.3939 1.0557 0.071 Uiso 1 1 calc R U . . .
H31C H -0.1781 0.3673 1.0009 0.071 Uiso 1 1 calc R U . . .
C32 C -0.0239(5) 0.14536(14) 1.02532(18) 0.0354(8) Uani 1 1 d . . . . .
H32A H 0.0893 0.1467 1.0419 0.042 Uiso 1 1 d R U . . .
H32B H -0.0766 0.1484 1.0675 0.042 Uiso 1 1 d R U . . .
C33 C -0.0669(6) 0.08436(15) 0.9873(2) 0.0508(11) Uani 1 1 d . . . . .
H33A H -0.1788 0.0835 0.9703 0.076 Uiso 1 1 calc R U . . .
H33B H -0.0385 0.0495 1.0202 0.076 Uiso 1 1 calc R U . . .
H33C H -0.0112 0.0805 0.9467 0.076 Uiso 1 1 calc R U . . .
C34 C 0.4332(3) 0.23432(12) 0.94308(15) 0.0186(5) Uani 1 1 d . . . . .
H34A H 0.4858 0.1988 0.9236 0.022 Uiso 1 1 d R U . . .
H34B H 0.4796 0.2732 0.9277 0.022 Uiso 1 1 d R U . . .
C35 C 0.4698(4) 0.23098(14) 1.02394(17) 0.0281(6) Uani 1 1 d . . . . .
H35A H 0.4215 0.2664 1.0445 0.042 Uiso 1 1 calc R U . . .
H35B H 0.5823 0.2325 1.0391 0.042 Uiso 1 1 calc R U . . .
H35C H 0.4290 0.1919 1.0403 0.042 Uiso 1 1 calc R U . . .


_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 C32 2.280(3) . ?
Bi1 C30 2.283(3) . ?
Bi1 In1 2.8535(2) . ?
In1 C34 2.197(3) . ?
In1 N2 2.210(2) . ?
In1 N1 2.212(2) . ?
N1 C1 1.328(3) . ?
N1 C6 1.439(3) . ?
N2 C3 1.329(3) . ?
N2 C18 1.441(3) . ?
C1 C2 1.409(3) . ?
C1 C4 1.516(3) . ?
C2 C3 1.410(3) . ?
C3 C5 1.516(3) . ?
C6 C11 1.405(3) . ?
C6 C7 1.406(3) . ?
C7 C8 1.397(3) . ?
C7 C12 1.516(4) . ?
C8 C9 1.384(4) . ?
C9 C10 1.380(4) . ?
C10 C11 1.396(3) . ?
C11 C15 1.518(4) . ?
C12 C14 1.531(4) . ?
C12 C13 1.538(5) . ?
C15 C17 1.532(4) . ?
C15 C16 1.538(3) . ?
C18 C23 1.411(3) . ?
C18 C19 1.411(3) . ?
C19 C20 1.401(3) . ?
C19 C24 1.513(4) . ?
C20 C21 1.380(4) . ?
C21 C22 1.382(4) . ?
C22 C23 1.393(3) . ?
C23 C27 1.518(4) . ?
C24 C25 1.530(4) . ?
C24 C26 1.534(4) . ?
C27 C29 1.522(4) . ?
C27 C28 1.534(4) . ?
C30 C31 1.508(5) . ?
C32 C33 1.511(5) . ?
C34 C35 1.523(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C32 Bi1 C30 92.93(13) . . ?
C32 Bi1 In1 95.50(9) . . ?
C30 Bi1 In1 95.19(10) . . ?
C34 In1 N2 104.41(9) . . ?
C34 In1 N1 105.21(9) . . ?
N2 In1 N1 86.72(7) . . ?
C34 In1 Bi1 133.43(7) . . ?
N2 In1 Bi1 107.87(5) . . ?
N1 In1 Bi1 109.24(5) . . ?
C1 N1 C6 119.76(19) . . ?
C1 N1 In1 119.94(15) . . ?
C6 N1 In1 119.97(15) . . ?
C3 N2 C18 119.94(19) . . ?
C3 N2 In1 119.50(15) . . ?
C18 N2 In1 120.21(15) . . ?
N1 C1 C2 124.4(2) . . ?
N1 C1 C4 119.6(2) . . ?
C2 C1 C4 116.0(2) . . ?
C1 C2 C3 129.8(2) . . ?
N2 C3 C2 125.2(2) . . ?
N2 C3 C5 119.08(19) . . ?
C2 C3 C5 115.7(2) . . ?
C11 C6 C7 120.8(2) . . ?
C11 C6 N1 120.7(2) . . ?
C7 C6 N1 118.4(2) . . ?
C8 C7 C6 118.5(2) . . ?
C8 C7 C12 119.9(2) . . ?
C6 C7 C12 121.6(2) . . ?
C9 C8 C7 121.1(2) . . ?
C10 C9 C8 119.7(2) . . ?
C9 C10 C11 121.3(2) . . ?
C10 C11 C6 118.5(2) . . ?
C10 C11 C15 119.2(2) . . ?
C6 C11 C15 122.3(2) . . ?
C7 C12 C14 112.9(2) . . ?
C7 C12 C13 110.7(3) . . ?
C14 C12 C13 109.7(3) . . ?
C11 C15 C17 109.6(2) . . ?
C11 C15 C16 112.5(2) . . ?
C17 C15 C16 110.5(2) . . ?
C23 C18 C19 120.7(2) . . ?
C23 C18 N2 118.5(2) . . ?
C19 C18 N2 120.8(2) . . ?
C20 C19 C18 118.2(2) . . ?
C20 C19 C24 119.0(2) . . ?
C18 C19 C24 122.8(2) . . ?
C21 C20 C19 121.4(3) . . ?
C20 C21 C22 119.8(2) . . ?
C21 C22 C23 121.4(3) . . ?
C22 C23 C18 118.6(2) . . ?
C22 C23 C27 119.9(2) . . ?
C18 C23 C27 121.5(2) . . ?
C19 C24 C25 109.6(2) . . ?
C19 C24 C26 112.8(2) . . ?
C25 C24 C26 110.0(2) . . ?
C23 C27 C29 112.0(2) . . ?
C23 C27 C28 112.7(2) . . ?
C29 C27 C28 109.9(3) . . ?
C31 C30 Bi1 112.5(3) . . ?
C33 C32 Bi1 110.5(3) . . ?
C35 C34 In1 117.18(19) . . ?

_refine_diff_density_max         3.281
_refine_diff_density_min         -1.236
_refine_diff_density_rms         0.125

_shelxl_version_number           2013-4

#######################################################################
#
#                 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_cg_013m

_database_code_CSD               ?
_database_code_depnum_ccdc_archive 'CCDC 1011106'

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H51 Ga N2'
_chemical_formula_sum            'C33 H51 Ga N2'
_chemical_formula_weight         545.47

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'
Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.3656(18)
_cell_length_b                   12.119(2)
_cell_length_c                   13.700(2)
_cell_angle_alpha                71.293(6)
_cell_angle_beta                 75.982(6)
_cell_angle_gamma                73.618(6)
_cell_volume                     1542.0(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    25181
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      31.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.380
_exptl_absorpt_coefficient_mu    0.914
_shelx_estimated_absorpt_T_min   0.678
_shelx_estimated_absorpt_T_max   0.723
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_process_details   
; 
 BRUKER AXS SMART APEX 2 Vers. 3.0-2009
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-RAY tube'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_measurement_device_type  
; 
 Bruker D8 KAPPA series II with APEX II area detector system
;
_diffrn_measurement_method       
;
 Data collection strategy APEX 2/COSMO
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            34092
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.077
_diffrn_reflns_theta_max         31.426
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9970
_reflns_number_gt                9330
_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       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_cell_refinement       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_data_reduction        'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_structure_solution    'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_structure_refinement  'BRUKER AXS Inc. 2013 Vers. 2013/4'
_computing_molecular_graphics    'BRUKER AXS Inc. 2008 Vers. 2008/4'
_computing_publication_material  'BRUKER AXS Inc. 2013 Vers. 2013/4'

_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
 The methyl groups are idealized with
 tetrahedral angles in a combined 
 rotating and rigid group refinement
 with the 1.5 fold isotropic displacement
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+0.6468P] 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         9970
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
Ga1 Ga 0.16614(2) 0.27520(2) 0.27410(2) 0.01319(4) Uani 1 1 d . . . . .
N1 N 0.21947(8) 0.43277(7) 0.21726(6) 0.01385(14) Uani 1 1 d . . . . .
N2 N 0.30801(8) 0.20102(7) 0.17314(7) 0.01422(14) Uani 1 1 d . . . . .
C1 C 0.27462(9) 0.46766(9) 0.11700(8) 0.01505(16) Uani 1 1 d . . . . .
C2 C 0.32011(10) 0.39231(9) 0.04981(8) 0.01622(17) Uani 1 1 d . . . . .
H2 H 0.3352 0.4313 -0.0236 0.019 Uiso 1 1 d R U . . .
C3 C 0.34597(9) 0.26732(9) 0.07695(8) 0.01513(16) Uani 1 1 d . . . . .
C4 C 0.29347(11) 0.59409(9) 0.06797(9) 0.02087(19) Uani 1 1 d . . . . .
H4A H 0.2177 0.6416 0.0306 0.031 Uiso 1 1 calc R U . . .
H4B H 0.3797 0.5934 0.0188 0.031 Uiso 1 1 calc R U . . .
H4C H 0.2952 0.6293 0.1227 0.031 Uiso 1 1 calc R U . . .
C5 C 0.42129(11) 0.20850(10) -0.00934(8) 0.02038(19) Uani 1 1 d . . . . .
H5A H 0.4799 0.1316 0.0203 0.031 Uiso 1 1 calc R U . . .
H5B H 0.4774 0.2604 -0.0614 0.031 Uiso 1 1 calc R U . . .
H5C H 0.3553 0.1955 -0.0427 0.031 Uiso 1 1 calc R U . . .
C6 C 0.18698(10) 0.51092(9) 0.28440(8) 0.01571(16) Uani 1 1 d . . . . .
C7 C 0.06256(11) 0.59594(9) 0.28747(8) 0.01778(17) Uani 1 1 d . . . . .
C8 C 0.03288(13) 0.66538(10) 0.35750(9) 0.0249(2) Uani 1 1 d . . . . .
H8 H -0.0528 0.7213 0.3615 0.030 Uiso 1 1 d R U . . .
C9 C 0.12303(15) 0.65324(12) 0.42192(10) 0.0306(3) Uani 1 1 d . . . . .
H9 H 0.1014 0.7021 0.4683 0.037 Uiso 1 1 calc R U . . .
C10 C 0.24525(14) 0.56914(11) 0.41815(10) 0.0279(2) Uani 1 1 d . . . . .
H10 H 0.3080 0.5604 0.4625 0.034 Uiso 1 1 d R U . . .
C11 C 0.27907(11) 0.49607(9) 0.35095(8) 0.01952(18) Uani 1 1 d . . . . .
C12 C -0.04045(11) 0.61570(9) 0.21788(9) 0.02054(19) Uani 1 1 d . . . . .
H12 H -0.0061 0.5603 0.1764 0.025 Uiso 1 1 d R U . . .
C13 C -0.06201(13) 0.74215(11) 0.14343(10) 0.0274(2) Uani 1 1 d . . . . .
H13A H -0.1038 0.8006 0.1840 0.041 Uiso 1 1 calc R U . . .
H13B H -0.1222 0.7490 0.0955 0.041 Uiso 1 1 calc R U . . .
H13C H 0.0261 0.7577 0.1032 0.041 Uiso 1 1 calc R U . . .
C14 C -0.17888(13) 0.59395(12) 0.28278(13) 0.0339(3) Uani 1 1 d . . . . .
H14A H -0.1654 0.5150 0.3333 0.051 Uiso 1 1 calc R U . . .
H14B H -0.2393 0.5975 0.2363 0.051 Uiso 1 1 calc R U . . .
H14C H -0.2202 0.6555 0.3201 0.051 Uiso 1 1 calc R U . . .
C15 C 0.41354(11) 0.40494(10) 0.34862(9) 0.02150(19) Uani 1 1 d . . . . .
H15 H 0.4002 0.3414 0.3278 0.026 Uiso 1 1 d R U . . .
C16 C 0.45780(17) 0.35092(15) 0.45640(13) 0.0428(4) Uani 1 1 d . . . . .
H16A H 0.4800 0.4126 0.4773 0.064 Uiso 1 1 calc R U . . .
H16B H 0.5383 0.2854 0.4529 0.064 Uiso 1 1 calc R U . . .
H16C H 0.3833 0.3203 0.5078 0.064 Uiso 1 1 calc R U . . .
C17 C 0.52490(15) 0.45707(16) 0.26666(16) 0.0494(4) Uani 1 1 d . . . . .
H17A H 0.4992 0.4808 0.1973 0.074 Uiso 1 1 calc R U . . .
H17B H 0.6109 0.3968 0.2680 0.074 Uiso 1 1 calc R U . . .
H17C H 0.5362 0.5271 0.2819 0.074 Uiso 1 1 calc R U . . .
C18 C 0.36396(10) 0.07466(9) 0.20435(8) 0.01558(16) Uani 1 1 d . . . . .
C19 C 0.29541(10) -0.00690(9) 0.19759(8) 0.01796(18) Uani 1 1 d . . . . .
C20 C 0.34842(11) -0.12895(9) 0.23610(9) 0.0220(2) Uani 1 1 d . . . . .
H20 H 0.3018 -0.1852 0.2327 0.026 Uiso 1 1 d R U . . .
C21 C 0.46662(12) -0.16954(10) 0.27900(10) 0.0253(2) Uani 1 1 d . . . . .
H21 H 0.5020 -0.2534 0.3046 0.030 Uiso 1 1 d R U . . .
C22 C 0.53397(12) -0.08835(10) 0.28471(10) 0.0246(2) Uani 1 1 d . . . . .
H22 H 0.6161 -0.1169 0.3139 0.030 Uiso 1 1 d R U . . .
C23 C 0.48413(10) 0.03418(9) 0.24880(8) 0.01855(18) Uani 1 1 d . . . . .
C24 C 0.16669(11) 0.03252(10) 0.15008(10) 0.0226(2) Uani 1 1 d . . . . .
H24 H 0.1439 0.1179 0.1288 0.027 Uiso 1 1 d R U . . .
C25 C 0.04734(13) -0.01097(12) 0.23053(13) 0.0340(3) Uani 1 1 d . . . . .
H25A H 0.0661 -0.0984 0.2496 0.051 Uiso 1 1 calc R U . . .
H25B H -0.0366 0.0221 0.2003 0.051 Uiso 1 1 calc R U . . .
H25C H 0.0363 0.0157 0.2930 0.051 Uiso 1 1 calc R U . . .
C26 C 0.18923(15) -0.01198(11) 0.05286(11) 0.0309(3) Uani 1 1 d . . . . .
H26A H 0.2649 0.0172 0.0020 0.046 Uiso 1 1 calc R U . . .
H26B H 0.1061 0.0180 0.0216 0.046 Uiso 1 1 calc R U . . .
H26C H 0.2110 -0.0995 0.0730 0.046 Uiso 1 1 calc R U . . .
C27 C 0.56067(11) 0.12087(10) 0.25550(9) 0.0216(2) Uani 1 1 d . . . . .
H27 H 0.4975 0.1956 0.2542 0.026 Uiso 1 1 d R U . . .
C28 C 0.62084(15) 0.08087(14) 0.35593(11) 0.0345(3) Uani 1 1 d . . . . .
H28A H 0.5481 0.0685 0.4165 0.052 Uiso 1 1 calc R U . . .
H28B H 0.6636 0.1425 0.3579 0.052 Uiso 1 1 calc R U . . .
H28C H 0.6894 0.0059 0.3579 0.052 Uiso 1 1 calc R U . . .
C29 C 0.67451(13) 0.14190(13) 0.16061(11) 0.0318(3) Uani 1 1 d . . . . .
H29A H 0.7389 0.0658 0.1580 0.048 Uiso 1 1 calc R U . . .
H29B H 0.7226 0.1977 0.1669 0.048 Uiso 1 1 calc R U . . .
H29C H 0.6346 0.1756 0.0965 0.048 Uiso 1 1 calc R U . . .
C30 C -0.02197(11) 0.29812(9) 0.24279(9) 0.0212(2) Uani 1 1 d . . . . .
H30A H -0.0459 0.2191 0.2668 0.025 Uiso 1 1 calc R U . . .
H30B H -0.0875 0.3486 0.2855 0.025 Uiso 1 1 calc R U . . .
C31 C -0.04345(12) 0.35340(11) 0.13044(10) 0.0259(2) Uani 1 1 d . . . . .
H31A H -0.0098 0.4272 0.1021 0.039 Uiso 1 1 calc R U . . .
H31B H -0.1409 0.3716 0.1274 0.039 Uiso 1 1 calc R U . . .
H31C H 0.0065 0.2972 0.0890 0.039 Uiso 1 1 calc R U . . .
C32 C 0.19814(11) 0.19337(10) 0.41944(8) 0.02094(19) Uani 1 1 d . . . . .
H32A H 0.2973 0.1628 0.4196 0.025 Uiso 1 1 calc R U . . .
H32B H 0.1644 0.2515 0.4618 0.025 Uiso 1 1 calc R U . . .
C33 C 0.12582(14) 0.08928(12) 0.46885(10) 0.0313(3) Uani 1 1 d . . . . .
H33A H 0.0295 0.1175 0.4611 0.047 Uiso 1 1 calc R U . . .
H33B H 0.1328 0.0580 0.5433 0.047 Uiso 1 1 calc R U . . .
H33C H 0.1690 0.0258 0.4338 0.047 Uiso 1 1 calc R U . . .


_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
Ga1 C32 1.9814(11) . ?
Ga1 N2 1.9876(9) . ?
Ga1 N1 1.9979(9) . ?
Ga1 C30 2.0215(12) . ?
N1 C1 1.3326(13) . ?
N1 C6 1.4441(13) . ?
N2 C3 1.3360(13) . ?
N2 C18 1.4365(12) . ?
C1 C2 1.4104(14) . ?
C1 C4 1.5107(14) . ?
C2 C3 1.4010(14) . ?
C3 C5 1.5149(14) . ?
C6 C7 1.4067(14) . ?
C6 C11 1.4122(14) . ?
C7 C8 1.3971(15) . ?
C7 C12 1.5196(15) . ?
C8 C9 1.3830(18) . ?
C9 C10 1.3857(18) . ?
C10 C11 1.3950(16) . ?
C11 C15 1.5153(15) . ?
C12 C13 1.5341(16) . ?
C12 C14 1.5375(17) . ?
C15 C17 1.5234(19) . ?
C15 C16 1.5356(18) . ?
C18 C19 1.4061(14) . ?
C18 C23 1.4122(14) . ?
C19 C20 1.3963(14) . ?
C19 C24 1.5145(15) . ?
C20 C21 1.3829(16) . ?
C21 C22 1.3875(17) . ?
C22 C23 1.3914(15) . ?
C23 C27 1.5195(15) . ?
C24 C25 1.5355(18) . ?
C24 C26 1.5358(18) . ?
C27 C28 1.5278(17) . ?
C27 C29 1.5368(18) . ?
C30 C31 1.5126(17) . ?
C32 C33 1.5334(16) . ?

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
C32 Ga1 N2 110.92(4) . . ?
C32 Ga1 N1 113.30(4) . . ?
N2 Ga1 N1 93.75(4) . . ?
C32 Ga1 C30 117.77(5) . . ?
N2 Ga1 C30 110.59(4) . . ?
N1 Ga1 C30 107.91(4) . . ?
C1 N1 C6 121.17(8) . . ?
C1 N1 Ga1 119.93(7) . . ?
C6 N1 Ga1 118.71(6) . . ?
C3 N2 C18 121.10(8) . . ?
C3 N2 Ga1 120.18(7) . . ?
C18 N2 Ga1 118.67(6) . . ?
N1 C1 C2 123.96(9) . . ?
N1 C1 C4 120.72(9) . . ?
C2 C1 C4 115.32(9) . . ?
C3 C2 C1 128.05(9) . . ?
N2 C3 C2 123.14(9) . . ?
N2 C3 C5 120.42(9) . . ?
C2 C3 C5 116.44(9) . . ?
C7 C6 C11 120.61(9) . . ?
C7 C6 N1 120.55(9) . . ?
C11 C6 N1 118.75(9) . . ?
C8 C7 C6 118.38(10) . . ?
C8 C7 C12 118.70(9) . . ?
C6 C7 C12 122.91(9) . . ?
C9 C8 C7 121.67(11) . . ?
C8 C9 C10 119.38(11) . . ?
C9 C10 C11 121.35(11) . . ?
C10 C11 C6 118.59(10) . . ?
C10 C11 C15 120.10(10) . . ?
C6 C11 C15 121.29(9) . . ?
C7 C12 C13 111.91(9) . . ?
C7 C12 C14 111.44(10) . . ?
C13 C12 C14 108.91(10) . . ?
C11 C15 C17 111.31(10) . . ?
C11 C15 C16 112.59(10) . . ?
C17 C15 C16 111.31(12) . . ?
C19 C18 C23 120.80(9) . . ?
C19 C18 N2 120.68(9) . . ?
C23 C18 N2 118.37(9) . . ?
C20 C19 C18 118.59(10) . . ?
C20 C19 C24 118.84(9) . . ?
C18 C19 C24 122.57(9) . . ?
C21 C20 C19 121.07(10) . . ?
C20 C21 C22 119.89(10) . . ?
C21 C22 C23 121.20(10) . . ?
C22 C23 C18 118.44(10) . . ?
C22 C23 C27 119.97(9) . . ?
C18 C23 C27 121.58(9) . . ?
C19 C24 C25 110.94(10) . . ?
C19 C24 C26 111.02(10) . . ?
C25 C24 C26 110.44(10) . . ?
C23 C27 C28 113.24(10) . . ?
C23 C27 C29 111.01(10) . . ?
C28 C27 C29 109.43(10) . . ?
C31 C30 Ga1 117.58(8) . . ?
C33 C32 Ga1 111.51(8) . . ?

_refine_diff_density_max         1.429
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4

#######################################################################
#
#                 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
#
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_cg_014m

_database_code_CSD               ?
_database_code_depnum_ccdc_archive 'CCDC 1011107'

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H56 Bi Ga N2'
_chemical_formula_sum            'C35 H56 Bi Ga N2'
_chemical_formula_weight         783.51

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'
Ga Ga 0.2307 1.6083 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.0994(6)
_cell_length_b                   12.0444(9)
_cell_length_c                   16.5176(12)
_cell_angle_alpha                74.379(2)
_cell_angle_beta                 79.774(2)
_cell_angle_gamma                85.921(2)
_cell_volume                     1715.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    42220
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      30.95

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             788
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.413
_exptl_crystal_size_min          0.254
_exptl_absorpt_coefficient_mu    5.932
_shelx_estimated_absorpt_T_min   0.163
_shelx_estimated_absorpt_T_max   0.314
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.12
_exptl_absorpt_correction_T_max  0.44
_exptl_absorpt_process_details   
; 
 BRUKER AXS SMART APEX 2 Vers. 3.0-2009
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-RAY tube'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_measurement_device_type  
; 
 Bruker D8 KAPPA series II with APEX II area detector system
;
_diffrn_measurement_method       
;
 Data collection strategy APEX 2/COSMO
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            55296
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.275
_diffrn_reflns_theta_max         30.978
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             10747
_reflns_number_gt                10176
_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       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_cell_refinement       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_data_reduction        'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_structure_solution    'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_structure_refinement  'BRUKER AXS Inc. 2013 Vers. 2013/4'
_computing_molecular_graphics    'BRUKER AXS Inc. 2008 Vers. 2008/4'
_computing_publication_material  'BRUKER AXS Inc. 2013 Vers. 2013/4'

_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
 The methyl groups are idealized with
 tetrahedral angles in a combined 
 rotating and rigid group refinement
 with the 1.5 fold isotropic displacement
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0269P)²+4.3490P] 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         10747
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0693
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Bi1 Bi 0.18249(2) 0.86252(2) 0.17724(2) 0.01345(3) Uani 1 1 d . . . . .
Ga1 Ga 0.45103(3) 0.79878(2) 0.22481(2) 0.00883(5) Uani 1 1 d . . . . .
N1 N 0.4852(2) 0.62912(18) 0.27506(14) 0.0105(4) Uani 1 1 d . . . . .
N2 N 0.4573(2) 0.83849(18) 0.33395(14) 0.0101(4) Uani 1 1 d . . . . .
C1 C 0.5578(3) 0.5932(2) 0.34060(16) 0.0106(4) Uani 1 1 d . . . . .
C2 C 0.5931(3) 0.6637(2) 0.38887(16) 0.0121(4) Uani 1 1 d . . . . .
H2 H 0.6642 0.6325 0.4252 0.015 Uiso 1 1 d R U . . .
C3 C 0.5363(3) 0.7748(2) 0.39098(16) 0.0104(4) Uani 1 1 d . . . . .
C4 C 0.6060(3) 0.4678(2) 0.36936(18) 0.0157(5) Uani 1 1 d . . . . .
H4A H 0.5496 0.4209 0.3460 0.024 Uiso 1 1 calc R U . . .
H4B H 0.5865 0.4421 0.4317 0.024 Uiso 1 1 calc R U . . .
H4C H 0.7130 0.4592 0.3489 0.024 Uiso 1 1 calc R U . . .
C5 C 0.5682(3) 0.8197(2) 0.46256(17) 0.0147(5) Uani 1 1 d . . . . .
H5A H 0.6613 0.8623 0.4443 0.022 Uiso 1 1 calc R U . . .
H5B H 0.5780 0.7549 0.5122 0.022 Uiso 1 1 calc R U . . .
H5C H 0.4859 0.8712 0.4778 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4396(3) 0.5482(2) 0.23475(16) 0.0123(4) Uani 1 1 d . . . . .
C7 C 0.5400(3) 0.5098(2) 0.17214(17) 0.0145(5) Uani 1 1 d . . . . .
C8 C 0.4881(3) 0.4339(2) 0.13319(19) 0.0184(5) Uani 1 1 d . . . . .
H8A H 0.5537 0.4092 0.0895 0.022 Uiso 1 1 d R U . . .
C9 C 0.3435(4) 0.3949(2) 0.1566(2) 0.0199(6) Uani 1 1 d . . . . .
H9 H 0.3116 0.3416 0.1305 0.024 Uiso 1 1 d R U . . .
C10 C 0.2459(3) 0.4335(2) 0.21798(19) 0.0173(5) Uani 1 1 d . . . . .
H10 H 0.1465 0.4068 0.2337 0.021 Uiso 1 1 d R U . . .
C11 C 0.2908(3) 0.5109(2) 0.25759(17) 0.0134(5) Uani 1 1 d . . . . .
C12 C 0.7017(3) 0.5454(2) 0.14539(18) 0.0178(5) Uani 1 1 d . . . . .
H12 H 0.7198 0.6017 0.1771 0.021 Uiso 1 1 d R U . . .
C13 C 0.8108(4) 0.4421(3) 0.1656(2) 0.0250(6) Uani 1 1 d . . . . .
H13A H 0.7898 0.4031 0.2266 0.037 Uiso 1 1 calc R U . . .
H13B H 0.9135 0.4694 0.1508 0.037 Uiso 1 1 calc R U . . .
H13C H 0.7986 0.3881 0.1324 0.037 Uiso 1 1 calc R U . . .
C14 C 0.7371(4) 0.6045(3) 0.0501(2) 0.0297(7) Uani 1 1 d . . . . .
H14A H 0.7318 0.5483 0.0175 0.045 Uiso 1 1 calc R U . . .
H14B H 0.8379 0.6354 0.0365 0.045 Uiso 1 1 calc R U . . .
H14C H 0.6644 0.6675 0.0352 0.045 Uiso 1 1 calc R U . . .
C15 C 0.1827(3) 0.5512(2) 0.32602(18) 0.0151(5) Uani 1 1 d . . . . .
H15 H 0.2069 0.6326 0.3213 0.018 Uiso 1 1 d R U . . .
C16 C 0.2053(4) 0.4795(3) 0.41492(19) 0.0260(6) Uani 1 1 d . . . . .
H16A H 0.1864 0.3983 0.4209 0.039 Uiso 1 1 calc R U . . .
H16B H 0.1357 0.5073 0.4581 0.039 Uiso 1 1 calc R U . . .
H16C H 0.3081 0.4869 0.4226 0.039 Uiso 1 1 calc R U . . .
C17 C 0.0192(3) 0.5513(3) 0.3155(2) 0.0223(6) Uani 1 1 d . . . . .
H17A H 0.0078 0.5945 0.2575 0.033 Uiso 1 1 calc R U . . .
H17B H -0.0431 0.5878 0.3565 0.033 Uiso 1 1 calc R U . . .
H17C H -0.0118 0.4718 0.3259 0.033 Uiso 1 1 calc R U . . .
C18 C 0.3797(3) 0.9421(2) 0.34785(16) 0.0102(4) Uani 1 1 d . . . . .
C19 C 0.2265(3) 0.9361(2) 0.38238(16) 0.0118(4) Uani 1 1 d . . . . .
C20 C 0.1491(3) 1.0383(2) 0.39051(18) 0.0156(5) Uani 1 1 d . . . . .
H20 H 0.0460 1.0360 0.4143 0.019 Uiso 1 1 d R U . . .
C21 C 0.2207(3) 1.1431(2) 0.36442(19) 0.0179(5) Uani 1 1 d . . . . .
H21 H 0.1662 1.2120 0.3691 0.021 Uiso 1 1 d R U . . .
C22 C 0.3716(3) 1.1473(2) 0.33170(18) 0.0159(5) Uani 1 1 d . . . . .
H22 H 0.4205 1.2190 0.3152 0.019 Uiso 1 1 d R U . . .
C23 C 0.4541(3) 1.0475(2) 0.32271(16) 0.0121(4) Uani 1 1 d . . . . .
C24 C 0.1480(3) 0.8221(2) 0.41382(17) 0.0138(5) Uani 1 1 d . . . . .
H24 H 0.1953 0.7719 0.3765 0.017 Uiso 1 1 d R U . . .
C25 C 0.1688(3) 0.7609(2) 0.50545(19) 0.0188(5) Uani 1 1 d . . . . .
H25A H 0.2755 0.7472 0.5079 0.028 Uiso 1 1 calc R U . . .
H25B H 0.1179 0.6871 0.5237 0.028 Uiso 1 1 calc R U . . .
H25C H 0.1261 0.8094 0.5433 0.028 Uiso 1 1 calc R U . . .
C26 C -0.0193(3) 0.8326(3) 0.4090(2) 0.0192(5) Uani 1 1 d . . . . .
H26A H -0.0707 0.8747 0.4494 0.029 Uiso 1 1 calc R U . . .
H26B H -0.0604 0.7554 0.4233 0.029 Uiso 1 1 calc R U . . .
H26C H -0.0337 0.8743 0.3511 0.029 Uiso 1 1 calc R U . . .
C27 C 0.6185(3) 1.0575(2) 0.28455(17) 0.0141(5) Uani 1 1 d . . . . .
H27 H 0.6599 0.9782 0.2850 0.017 Uiso 1 1 d R U . . .
C28 C 0.7060(3) 1.1093(3) 0.3361(2) 0.0215(6) Uani 1 1 d . . . . .
H28A H 0.6683 1.1879 0.3350 0.032 Uiso 1 1 calc R U . . .
H28B H 0.8122 1.1113 0.3111 0.032 Uiso 1 1 calc R U . . .
H28C H 0.6935 1.0619 0.3952 0.032 Uiso 1 1 calc R U . . .
C29 C 0.6389(3) 1.1297(3) 0.19187(19) 0.0208(6) Uani 1 1 d . . . . .
H29A H 0.5780 1.0987 0.1601 0.031 Uiso 1 1 calc R U . . .
H29B H 0.7443 1.1270 0.1661 0.031 Uiso 1 1 calc R U . . .
H29C H 0.6074 1.2098 0.1900 0.031 Uiso 1 1 calc R U . . .
C30 C 0.6214(3) 0.8573(2) 0.13370(18) 0.0165(5) Uani 1 1 d . . . . .
H30A H 0.6207 0.8181 0.0882 0.020 Uiso 1 1 calc R U . . .
H30B H 0.6008 0.9402 0.1091 0.020 Uiso 1 1 calc R U . . .
C31 C 0.7799(3) 0.8460(3) 0.1536(2) 0.0226(6) Uani 1 1 d . . . . .
H31A H 0.7885 0.8935 0.1922 0.034 Uiso 1 1 calc R U . . .
H31B H 0.8507 0.8721 0.1006 0.034 Uiso 1 1 calc R U . . .
H31C H 0.8024 0.7652 0.1808 0.034 Uiso 1 1 calc R U . . .
C32 C 0.2370(3) 1.0546(2) 0.1369(2) 0.0204(5) Uani 1 1 d . . . . .
H32A H 0.2807 1.0743 0.1819 0.024 Uiso 1 1 calc R U . . .
H32B H 0.3114 1.0713 0.0838 0.024 Uiso 1 1 calc R U . . .
C33 C 0.0962(4) 1.1270(3) 0.1222(3) 0.0396(10) Uani 1 1 d . . . . .
H33A H 0.0553 1.1093 0.0763 0.059 Uiso 1 1 calc R U . . .
H33B H 0.1200 1.2090 0.1064 0.059 Uiso 1 1 calc R U . . .
H33C H 0.0224 1.1097 0.1747 0.059 Uiso 1 1 calc R U . . .
C34 C 0.2540(4) 0.8401(3) 0.0429(2) 0.0235(6) Uani 1 1 d . . . . .
H34A H 0.1987 0.8970 0.0031 0.028 Uiso 1 1 calc R U . . .
H34B H 0.3619 0.8553 0.0244 0.028 Uiso 1 1 calc R U . . .
C35 C 0.2243(6) 0.7196(3) 0.0390(2) 0.0369(9) Uani 1 1 d . . . . .
H35A H 0.2895 0.6639 0.0720 0.055 Uiso 1 1 calc R U . . .
H35B H 0.2445 0.7156 -0.0205 0.055 Uiso 1 1 calc R U . . .
H35C H 0.1197 0.7013 0.0629 0.055 Uiso 1 1 calc R U . . .


_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 C34 2.282(3) . ?
Bi1 C32 2.293(3) . ?
Bi1 Ga1 2.6959(3) . ?
Ga1 C30 1.980(3) . ?
Ga1 N2 1.997(2) . ?
Ga1 N1 2.012(2) . ?
N1 C1 1.325(3) . ?
N1 C6 1.439(3) . ?
N2 C3 1.328(3) . ?
N2 C18 1.442(3) . ?
C1 C2 1.398(4) . ?
C1 C4 1.514(3) . ?
C2 C3 1.406(3) . ?
C3 C5 1.505(4) . ?
C6 C7 1.407(4) . ?
C6 C11 1.411(4) . ?
C7 C8 1.399(4) . ?
C7 C12 1.517(4) . ?
C8 C9 1.383(4) . ?
C9 C10 1.382(4) . ?
C10 C11 1.393(4) . ?
C11 C15 1.521(4) . ?
C12 C14 1.528(4) . ?
C12 C13 1.537(4) . ?
C15 C17 1.527(4) . ?
C15 C16 1.531(4) . ?
C18 C19 1.408(4) . ?
C18 C23 1.408(3) . ?
C19 C20 1.400(3) . ?
C19 C24 1.513(4) . ?
C20 C21 1.388(4) . ?
C21 C22 1.383(4) . ?
C22 C23 1.399(4) . ?
C23 C27 1.516(4) . ?
C24 C25 1.533(4) . ?
C24 C26 1.533(4) . ?
C27 C29 1.530(4) . ?
C27 C28 1.532(4) . ?
C30 C31 1.524(4) . ?
C32 C33 1.516(4) . ?
C34 C35 1.515(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C34 Bi1 C32 93.63(12) . . ?
C34 Bi1 Ga1 94.66(9) . . ?
C32 Bi1 Ga1 92.83(8) . . ?
C30 Ga1 N2 113.91(11) . . ?
C30 Ga1 N1 108.82(10) . . ?
N2 Ga1 N1 93.39(9) . . ?
C30 Ga1 Bi1 113.47(8) . . ?
N2 Ga1 Bi1 109.40(6) . . ?
N1 Ga1 Bi1 116.36(6) . . ?
C1 N1 C6 120.6(2) . . ?
C1 N1 Ga1 120.35(17) . . ?
C6 N1 Ga1 118.89(16) . . ?
C3 N2 C18 120.3(2) . . ?
C3 N2 Ga1 121.39(17) . . ?
C18 N2 Ga1 118.23(16) . . ?
N1 C1 C2 124.5(2) . . ?
N1 C1 C4 120.5(2) . . ?
C2 C1 C4 115.1(2) . . ?
C1 C2 C3 128.4(2) . . ?
N2 C3 C2 123.0(2) . . ?
N2 C3 C5 120.4(2) . . ?
C2 C3 C5 116.6(2) . . ?
C7 C6 C11 120.8(2) . . ?
C7 C6 N1 120.7(2) . . ?
C11 C6 N1 118.5(2) . . ?
C8 C7 C6 118.2(3) . . ?
C8 C7 C12 118.4(2) . . ?
C6 C7 C12 123.4(2) . . ?
C9 C8 C7 121.4(3) . . ?
C10 C9 C8 119.8(3) . . ?
C9 C10 C11 121.2(3) . . ?
C10 C11 C6 118.6(3) . . ?
C10 C11 C15 120.5(2) . . ?
C6 C11 C15 120.8(2) . . ?
C7 C12 C14 111.7(3) . . ?
C7 C12 C13 112.0(2) . . ?
C14 C12 C13 108.2(3) . . ?
C17 C15 C11 113.5(2) . . ?
C17 C15 C16 110.6(2) . . ?
C11 C15 C16 110.6(2) . . ?
C19 C18 C23 121.2(2) . . ?
C19 C18 N2 118.4(2) . . ?
C23 C18 N2 120.3(2) . . ?
C20 C19 C18 118.2(2) . . ?
C20 C19 C24 120.4(2) . . ?
C18 C19 C24 121.3(2) . . ?
C21 C20 C19 121.0(3) . . ?
C22 C21 C20 120.0(2) . . ?
C21 C22 C23 121.1(3) . . ?
C22 C23 C18 118.4(2) . . ?
C22 C23 C27 118.9(2) . . ?
C18 C23 C27 122.7(2) . . ?
C19 C24 C25 111.4(2) . . ?
C19 C24 C26 113.7(2) . . ?
C25 C24 C26 109.0(2) . . ?
C23 C27 C29 110.6(2) . . ?
C23 C27 C28 111.8(2) . . ?
C29 C27 C28 110.0(2) . . ?
C31 C30 Ga1 120.4(2) . . ?
C33 C32 Bi1 110.0(2) . . ?
C35 C34 Bi1 111.5(2) . . ?

_refine_diff_density_max         2.736
_refine_diff_density_min         -2.248
_refine_diff_density_rms         0.133

_shelxl_version_number           2013-4

#######################################################################
#
#                 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_cg_016m

_database_code_CSD               ?
_database_code_depnum_ccdc_archive 'CCDC 1011108'


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H56 Al Bi N2'
_chemical_formula_sum            'C35 H56 Al Bi N2'
_chemical_formula_weight         740.77

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'
Al Al 0.0645 0.0514 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   11.5940(15)
_cell_length_b                   12.2244(16)
_cell_length_c                   12.6546(16)
_cell_angle_alpha                72.804(6)
_cell_angle_beta                 88.915(6)
_cell_angle_gamma                89.682(6)
_cell_volume                     1713.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      30.04

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    5.196
_shelx_estimated_absorpt_T_min   0.324
_shelx_estimated_absorpt_T_max   0.408
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.38
_exptl_absorpt_correction_T_max  0.54
_exptl_absorpt_process_details   
; 
 BRUKER AXS SMART APEX 2 Vers. 3.0-2009
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-RAY tube'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_measurement_device_type  
; 
 Bruker D8 KAPPA series II with APEX II area detector system
;
_diffrn_measurement_method       
;
 Data collection strategy APEX 2/COSMO
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            48941
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.035
_diffrn_reflns_theta_max         30.086
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9813
_reflns_number_gt                9302
_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       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_cell_refinement       'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_data_reduction        'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_structure_solution    'BRUKER D8 KAPPA APEX 2 Vers. 3.0-2009'
_computing_structure_refinement  'BRUKER AXS Inc. 2013 Vers. 2013/4'
_computing_molecular_graphics    'BRUKER AXS Inc. 2008 Vers. 2008/4'
_computing_publication_material  'BRUKER AXS Inc. 2013 Vers. 2013/4'

_refine_special_details          
;
 Treatment of hydrogen atoms:    
 Riding model on idealized geometries 
 with the 1.2 fold isotropic displacement 
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
 The methyl groups are idealized with
 tetrahedral angles in a combined 
 rotating and rigid group refinement
 with the 1.5 fold isotropic displacement
 parameters of the equivalent Uij of the 
 corresponding carbon atom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0229P)²+1.0471P] 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         9813
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0194
_refine_ls_R_factor_gt           0.0175
_refine_ls_wR_factor_ref         0.0437
_refine_ls_wR_factor_gt          0.0430
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.004
_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
Bi1 Bi 0.47677(2) 0.70704(2) 0.67272(2) 0.01587(2) Uani 1 1 d . . . . .
Al1 Al 0.26784(4) 0.67434(4) 0.78495(4) 0.01090(9) Uani 1 1 d . . . . .
N1 N 0.14667(12) 0.61558(11) 0.71489(11) 0.0114(2) Uani 1 1 d . . . . .
N2 N 0.19205(12) 0.81655(11) 0.77877(11) 0.0115(2) Uani 1 1 d . . . . .
C1 C 0.03762(14) 0.64602(14) 0.72471(13) 0.0129(3) Uani 1 1 d . . . . .
C2 C 0.00566(14) 0.73691(14) 0.76576(14) 0.0147(3) Uani 1 1 d . . . . .
H2 H -0.0736 0.7408 0.7849 0.018 Uiso 1 1 d R U . . .
C3 C 0.07732(14) 0.82240(14) 0.78180(13) 0.0132(3) Uani 1 1 d . . . . .
C4 C -0.05938(15) 0.58389(16) 0.68884(15) 0.0191(3) Uani 1 1 d . . . . .
H4A H -0.0349 0.5626 0.6230 0.029 Uiso 1 1 calc R U . . .
H4B H -0.1270 0.6341 0.6715 0.029 Uiso 1 1 calc R U . . .
H4C H -0.0792 0.5147 0.7488 0.029 Uiso 1 1 calc R U . . .
C5 C 0.01725(16) 0.92464(15) 0.80241(16) 0.0200(3) Uani 1 1 d . . . . .
H5A H 0.0030 0.9098 0.8820 0.030 Uiso 1 1 calc R U . . .
H5B H -0.0563 0.9378 0.7638 0.030 Uiso 1 1 calc R U . . .
H5C H 0.0662 0.9926 0.7748 0.030 Uiso 1 1 calc R U . . .
C6 C 0.17463(14) 0.53056(14) 0.65893(13) 0.0125(3) Uani 1 1 d . . . . .
C7 C 0.21596(15) 0.56959(14) 0.54839(13) 0.0146(3) Uani 1 1 d . . . . .
C8 C 0.25291(16) 0.48834(15) 0.49788(14) 0.0188(3) Uani 1 1 d . . . . .
H8 H 0.2822 0.5130 0.4240 0.023 Uiso 1 1 d R U . . .
C9 C 0.24750(17) 0.37188(15) 0.55303(15) 0.0199(3) Uani 1 1 d . . . . .
H9 H 0.2741 0.3178 0.5174 0.024 Uiso 1 1 d R U . . .
C10 C 0.20332(16) 0.33473(15) 0.65987(15) 0.0184(3) Uani 1 1 d . . . . .
H10 H 0.1985 0.2549 0.6966 0.022 Uiso 1 1 d R U . . .
C11 C 0.16588(15) 0.41271(14) 0.71504(14) 0.0151(3) Uani 1 1 d . . . . .
C12 C 0.21884(16) 0.69668(15) 0.48442(13) 0.0174(3) Uani 1 1 d . . . . .
H12 H 0.2456 0.7390 0.5360 0.021 Uiso 1 1 d R U . . .
C13 C 0.0987(2) 0.74188(19) 0.44599(17) 0.0294(4) Uani 1 1 d . . . . .
H13A H 0.0639 0.6930 0.4062 0.044 Uiso 1 1 calc R U . . .
H13B H 0.1050 0.8204 0.3967 0.044 Uiso 1 1 calc R U . . .
H13C H 0.0501 0.7412 0.5104 0.044 Uiso 1 1 calc R U . . .
C14 C 0.3025(2) 0.72452(17) 0.38587(16) 0.0272(4) Uani 1 1 d . . . . .
H14A H 0.3796 0.6964 0.4110 0.041 Uiso 1 1 calc R U . . .
H14B H 0.3053 0.8076 0.3515 0.041 Uiso 1 1 calc R U . . .
H14C H 0.2765 0.6874 0.3317 0.041 Uiso 1 1 calc R U . . .
C15 C 0.12028(18) 0.36472(15) 0.83295(15) 0.0215(4) Uani 1 1 d . . . . .
H15 H 0.0949 0.4304 0.8598 0.026 Uiso 1 1 d R U . . .
C16 C 0.0167(2) 0.28585(18) 0.83971(19) 0.0336(5) Uani 1 1 d . . . . .
H16A H -0.0448 0.3284 0.7929 0.050 Uiso 1 1 calc R U . . .
H16B H -0.0114 0.2580 0.9165 0.050 Uiso 1 1 calc R U . . .
H16C H 0.0400 0.2207 0.8141 0.050 Uiso 1 1 calc R U . . .
C17 C 0.2133(2) 0.29753(19) 0.91071(17) 0.0348(5) Uani 1 1 d . . . . .
H17A H 0.2354 0.2298 0.8887 0.052 Uiso 1 1 calc R U . . .
H17B H 0.1828 0.2735 0.9868 0.052 Uiso 1 1 calc R U . . .
H17C H 0.2810 0.3464 0.9062 0.052 Uiso 1 1 calc R U . . .
C18 C 0.26114(14) 0.91689(13) 0.77300(13) 0.0124(3) Uani 1 1 d . . . . .
C19 C 0.29832(14) 0.93889(14) 0.86990(13) 0.0140(3) Uani 1 1 d . . . . .
C20 C 0.37358(16) 1.03062(15) 0.85923(15) 0.0177(3) Uani 1 1 d . . . . .
H20 H 0.3999 1.0459 0.9241 0.021 Uiso 1 1 d R U . . .
C21 C 0.41090(16) 1.09940(15) 0.75651(15) 0.0182(3) Uani 1 1 d . . . . .
H21 H 0.4634 1.1603 0.7511 0.022 Uiso 1 1 d R U . . .
C22 C 0.37080(15) 1.07859(14) 0.66143(14) 0.0166(3) Uani 1 1 d . . . . .
H22 H 0.3957 1.1263 0.5910 0.020 Uiso 1 1 d R U . . .
C23 C 0.29482(14) 0.98870(13) 0.66735(13) 0.0133(3) Uani 1 1 d . . . . .
C24 C 0.25789(16) 0.86959(15) 0.98522(14) 0.0172(3) Uani 1 1 d . . . . .
H24 H 0.2057 0.8076 0.9777 0.021 Uiso 1 1 d R U . . .
C25 C 0.35824(19) 0.81360(19) 1.05856(16) 0.0268(4) Uani 1 1 d . . . . .
H25A H 0.4073 0.7725 1.0191 0.040 Uiso 1 1 calc R U . . .
H25B H 0.3279 0.7597 1.1269 0.040 Uiso 1 1 calc R U . . .
H25C H 0.4037 0.8728 1.0766 0.040 Uiso 1 1 calc R U . . .
C26 C 0.18935(19) 0.94489(18) 1.04215(17) 0.0274(4) Uani 1 1 d . . . . .
H26A H 0.2399 1.0046 1.0529 0.041 Uiso 1 1 calc R U . . .
H26B H 0.1598 0.8975 1.1141 0.041 Uiso 1 1 calc R U . . .
H26C H 0.1246 0.9806 0.9958 0.041 Uiso 1 1 calc R U . . .
C27 C 0.24517(16) 0.97555(14) 0.56176(13) 0.0161(3) Uani 1 1 d . . . . .
H27 H 0.2095 0.8977 0.5796 0.019 Uiso 1 1 d R U . . .
C28 C 0.14985(18) 1.06428(18) 0.51962(17) 0.0254(4) Uani 1 1 d . . . . .
H28A H 0.0918 1.0579 0.5785 0.038 Uiso 1 1 calc R U . . .
H28B H 0.1134 1.0503 0.4555 0.038 Uiso 1 1 calc R U . . .
H28C H 0.1834 1.1413 0.4979 0.038 Uiso 1 1 calc R U . . .
C29 C 0.33598(18) 0.98494(17) 0.47048(15) 0.0225(4) Uani 1 1 d . . . . .
H29A H 0.2991 0.9750 0.4049 0.034 Uiso 1 1 calc R U . . .
H29B H 0.3945 0.9254 0.4965 0.034 Uiso 1 1 calc R U . . .
H29C H 0.3726 1.0605 0.4515 0.034 Uiso 1 1 calc R U . . .
C30 C 0.29011(17) 0.57919(16) 0.93881(15) 0.0213(4) Uani 1 1 d . . . . .
H30A H 0.3238 0.5055 0.9361 0.026 Uiso 1 1 calc R U . . .
H30B H 0.3487 0.6175 0.9714 0.026 Uiso 1 1 calc R U . . .
C31 C 0.1877(2) 0.55194(17) 1.01827(15) 0.0271(4) Uani 1 1 d . . . . .
H31A H 0.1503 0.6233 1.0204 0.041 Uiso 1 1 calc R U . . .
H31B H 0.2141 0.5102 1.0924 0.041 Uiso 1 1 calc R U . . .
H31C H 0.1326 0.5047 0.9934 0.041 Uiso 1 1 calc R U . . .
C32 C 0.55654(17) 0.79215(18) 0.79295(17) 0.0247(4) Uani 1 1 d . . . . .
H32A H 0.5358 0.8744 0.7707 0.030 Uiso 1 1 calc R U . . .
H32B H 0.5246 0.7564 0.8683 0.030 Uiso 1 1 calc R U . . .
C33 C 0.68694(17) 0.78014(18) 0.79442(17) 0.0253(4) Uani 1 1 d . . . . .
H33A H 0.7076 0.6992 0.8249 0.038 Uiso 1 1 calc R U . . .
H33B H 0.7192 0.8239 0.8405 0.038 Uiso 1 1 calc R U . . .
H33C H 0.7182 0.8095 0.7188 0.038 Uiso 1 1 calc R U . . .
C34 C 0.54357(17) 0.52891(17) 0.76738(17) 0.0238(4) Uani 1 1 d . . . . .
H34A H 0.6281 0.5256 0.7559 0.029 Uiso 1 1 calc R U . . .
H34B H 0.5279 0.5143 0.8475 0.029 Uiso 1 1 calc R U . . .
C35 C 0.48558(19) 0.43782(18) 0.7280(2) 0.0339(5) Uani 1 1 d . . . . .
H35A H 0.4026 0.4375 0.7442 0.051 Uiso 1 1 calc R U . . .
H35B H 0.5182 0.3627 0.7662 0.051 Uiso 1 1 calc R U . . .
H35C H 0.4984 0.4542 0.6480 0.051 Uiso 1 1 calc R U . . .


_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 C34 2.2914(19) . ?
Bi1 C32 2.292(2) . ?
Bi1 Al1 2.7549(6) . ?
Al1 N2 1.9250(14) . ?
Al1 N1 1.9262(15) . ?
Al1 C30 1.9716(18) . ?
N1 C1 1.330(2) . ?
N1 C6 1.452(2) . ?
N2 C3 1.332(2) . ?
N2 C18 1.452(2) . ?
C1 C2 1.404(2) . ?
C1 C4 1.510(2) . ?
C2 C3 1.402(2) . ?
C3 C5 1.514(2) . ?
C6 C11 1.409(2) . ?
C6 C7 1.413(2) . ?
C7 C8 1.393(2) . ?
C7 C12 1.525(2) . ?
C8 C9 1.389(3) . ?
C9 C10 1.382(2) . ?
C10 C11 1.401(2) . ?
C11 C15 1.518(2) . ?
C12 C14 1.523(2) . ?
C12 C13 1.530(3) . ?
C15 C16 1.529(3) . ?
C15 C17 1.536(3) . ?
C18 C19 1.406(2) . ?
C18 C23 1.414(2) . ?
C19 C20 1.398(2) . ?
C19 C24 1.521(2) . ?
C20 C21 1.386(2) . ?
C21 C22 1.390(3) . ?
C22 C23 1.396(2) . ?
C23 C27 1.516(2) . ?
C24 C25 1.530(3) . ?
C24 C26 1.536(3) . ?
C27 C29 1.527(2) . ?
C27 C28 1.533(3) . ?
C30 C31 1.514(3) . ?
C32 C33 1.518(3) . ?
C34 C35 1.513(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C34 Bi1 C32 93.29(8) . . ?
C34 Bi1 Al1 93.33(5) . . ?
C32 Bi1 Al1 92.72(5) . . ?
N2 Al1 N1 95.84(6) . . ?
N2 Al1 C30 111.62(7) . . ?
N1 Al1 C30 111.80(8) . . ?
N2 Al1 Bi1 112.39(4) . . ?
N1 Al1 Bi1 115.09(4) . . ?
C30 Al1 Bi1 109.56(6) . . ?
C1 N1 C6 120.31(14) . . ?
C1 N1 Al1 120.37(11) . . ?
C6 N1 Al1 119.13(11) . . ?
C3 N2 C18 120.26(13) . . ?
C3 N2 Al1 120.37(11) . . ?
C18 N2 Al1 119.36(10) . . ?
N1 C1 C2 123.20(15) . . ?
N1 C1 C4 120.41(15) . . ?
C2 C1 C4 116.38(15) . . ?
C3 C2 C1 127.41(15) . . ?
N2 C3 C2 123.05(15) . . ?
N2 C3 C5 120.68(15) . . ?
C2 C3 C5 116.27(15) . . ?
C11 C6 C7 121.11(14) . . ?
C11 C6 N1 120.84(14) . . ?
C7 C6 N1 117.98(14) . . ?
C8 C7 C6 118.12(15) . . ?
C8 C7 C12 120.27(15) . . ?
C6 C7 C12 121.60(14) . . ?
C9 C8 C7 121.43(16) . . ?
C10 C9 C8 119.84(16) . . ?
C9 C10 C11 121.14(16) . . ?
C10 C11 C6 118.29(15) . . ?
C10 C11 C15 117.76(15) . . ?
C6 C11 C15 123.94(15) . . ?
C14 C12 C7 113.05(15) . . ?
C14 C12 C13 109.70(16) . . ?
C7 C12 C13 111.60(16) . . ?
C11 C15 C16 111.73(16) . . ?
C11 C15 C17 111.82(17) . . ?
C16 C15 C17 108.39(17) . . ?
C19 C18 C23 120.93(15) . . ?
C19 C18 N2 120.84(14) . . ?
C23 C18 N2 118.16(14) . . ?
C20 C19 C18 118.27(15) . . ?
C20 C19 C24 118.66(15) . . ?
C18 C19 C24 123.05(15) . . ?
C21 C20 C19 121.62(17) . . ?
C20 C21 C22 119.43(16) . . ?
C21 C22 C23 121.29(15) . . ?
C22 C23 C18 118.39(15) . . ?
C22 C23 C27 119.42(14) . . ?
C18 C23 C27 122.08(15) . . ?
C19 C24 C25 112.26(15) . . ?
C19 C24 C26 110.90(15) . . ?
C25 C24 C26 109.08(16) . . ?
C23 C27 C29 113.21(15) . . ?
C23 C27 C28 110.21(14) . . ?
C29 C27 C28 109.78(15) . . ?
C31 C30 Al1 119.49(14) . . ?
C33 C32 Bi1 111.32(13) . . ?
C35 C34 Bi1 110.49(14) . . ?

_refine_diff_density_max         1.407
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.081

_shelxl_version_number           2013-4

