#------------------------------------------------------------------------------
#$Date: 2017-07-26 05:08:44 +0300 (Wed, 26 Jul 2017) $
#$Revision: 199332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/38/7043810.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7043810
loop_
_publ_author_name
'Waters, Jordan'
'Chen, Qien'
'Everitt, Thomas'
'Goicoechea, Jose M.'
_publ_section_title
;
 N-heterocyclic carbene adducts of the heavier group 15 tribromides.
 Normal to abnormal isomerism and bromide ion abstraction.
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT02431B
_journal_year                    2017
_chemical_formula_moiety         'C27 H36 Bi Br3 N2, 2(C4 H8 O)'
_chemical_formula_sum            'C35 H52 Bi Br3 N2 O2'
_chemical_formula_weight         981.49
_chemical_name_systematic
;
 (aIPr)BiBr3*2THF
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-07-04 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                98.77(3)
_cell_angle_beta                 102.17(3)
_cell_angle_gamma                96.09(3)
_cell_formula_units_Z            2
_cell_length_a                   11.105(2)
_cell_length_b                   11.908(2)
_cell_length_c                   15.263(3)
_cell_measurement_reflns_used    1368
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      40.80
_cell_measurement_theta_min      3.62
_cell_volume                     1929.9(7)
_computing_cell_refinement
;
KappaCCD software "DENZO" (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
KappaCCD software "Collect" (Nonius, 2000)
;
_computing_data_reduction
;
KappaCCD software "DENZO" (Otwinowski & Minor, 1996)
;
_computing_molecular_graphics    'WinGX (Farrugia, 2005)'
_computing_publication_material  'XCIF (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31667
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         5.121
_exptl_absorpt_coefficient_mu    7.705
_exptl_absorpt_correction_T_max  0.372
_exptl_absorpt_correction_T_min  0.228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_refine_diff_density_max         1.504
_refine_diff_density_min         -1.483
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         6703
_refine_ls_number_restraints     50
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0751P)²+4.2580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1263
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5830
_reflns_number_total             6703
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt02431b2.cif
_cod_data_source_block           6
_cod_original_cell_volume        1929.7(7)
_cod_database_code               7043810
_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.
;
_shelx_estimated_absorpt_t_min   0.259
_shelx_estimated_absorpt_t_max   0.372
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.37359(2) 0.94996(2) 0.35560(2) 0.04778(12) Uani 1 1 d . . . . .
Br1 Br 0.17290(8) 0.78528(10) 0.29461(8) 0.0855(3) Uani 1 1 d . . . . .
Br2 Br 0.61630(7) 1.10177(5) 0.45204(5) 0.05190(19) Uani 1 1 d . . . . .
Br3 Br 0.36059(10) 1.02533(10) 0.19786(7) 0.0860(3) Uani 1 1 d . . . . .
C1 C 0.6328(6) 0.7051(5) 0.2859(5) 0.0443(15) Uani 1 1 d . . . . .
H1 H 0.6830 0.6692 0.2499 0.053 Uiso 1 1 calc R U . . .
C2 C 0.5394(6) 0.7528(5) 0.3968(4) 0.0377(13) Uani 1 1 d . . . . .
H2 H 0.5136 0.7544 0.4525 0.045 Uiso 1 1 calc R U . . .
C3 C 0.5015(6) 0.8167(5) 0.3321(4) 0.0391(13) Uani 1 1 d . . . . .
C4 C 0.6881(6) 0.6069(5) 0.4179(5) 0.0478(16) Uani 1 1 d . . . . .
C5 C 0.6371(7) 0.4896(5) 0.3956(5) 0.0538(19) Uani 1 1 d . . . . .
C6 C 0.7020(9) 0.4180(7) 0.4468(7) 0.069(2) Uani 1 1 d . . . . .
H6 H 0.6706 0.3386 0.4362 0.082 Uiso 1 1 calc R U . . .
C7 C 0.8088(9) 0.4585(7) 0.5114(8) 0.075(3) Uani 1 1 d . . . . .
H7 H 0.8510 0.4072 0.5444 0.090 Uiso 1 1 calc R U . . .
C8 C 0.8563(8) 0.5741(7) 0.5294(7) 0.069(2) Uani 1 1 d . . . . .
H8 H 0.9307 0.6010 0.5749 0.083 Uiso 1 1 calc R U . . .
C9 C 0.7967(7) 0.6523(6) 0.4818(6) 0.0578(19) Uani 1 1 d . . . . .
C10 C 0.5195(8) 0.4434(6) 0.3234(6) 0.061(2) Uani 1 1 d . . . . .
H10 H 0.4847 0.5093 0.2987 0.073 Uiso 1 1 calc R U . . .
C11 C 0.5482(13) 0.3618(9) 0.2452(8) 0.105(4) Uani 1 1 d . . . . .
H11A H 0.6172 0.3993 0.2244 0.158 Uiso 1 1 calc R U . . .
H11B H 0.4743 0.3420 0.1946 0.158 Uiso 1 1 calc R U . . .
H11C H 0.5714 0.2917 0.2664 0.158 Uiso 1 1 calc R U . . .
C12 C 0.4221(10) 0.3804(9) 0.3622(8) 0.089(3) Uani 1 1 d . . . . .
H12A H 0.4516 0.3111 0.3810 0.134 Uiso 1 1 calc R U . . .
H12B H 0.3440 0.3588 0.3156 0.134 Uiso 1 1 calc R U . . .
H12C H 0.4079 0.4307 0.4151 0.134 Uiso 1 1 calc R U . . .
C13 C 0.8490(7) 0.7786(6) 0.5037(7) 0.062(2) Uani 1 1 d . . . . .
H13 H 0.7954 0.8177 0.4601 0.075 Uiso 1 1 calc R U . . .
C14 C 0.9800(8) 0.7999(8) 0.4906(7) 0.075(2) Uani 1 1 d . . . . .
H14A H 1.0357 0.7649 0.5340 0.113 Uiso 1 1 calc R U . . .
H14B H 1.0077 0.8827 0.5011 0.113 Uiso 1 1 calc R U . . .
H14C H 0.9817 0.7658 0.4283 0.113 Uiso 1 1 calc R U . . .
C15 C 0.8432(9) 0.8330(7) 0.6000(8) 0.083(3) Uani 1 1 d . . . . .
H15A H 0.7576 0.8190 0.6071 0.125 Uiso 1 1 calc R U . . .
H15B H 0.8705 0.9159 0.6099 0.125 Uiso 1 1 calc R U . . .
H15C H 0.8980 0.7989 0.6446 0.125 Uiso 1 1 calc R U . . .
C16 C 0.5545(7) 0.8172(6) 0.1744(5) 0.0493(16) Uani 1 1 d . . . . .
C17 C 0.4610(10) 0.7562(10) 0.1013(6) 0.085(3) Uani 1 1 d . . . . .
C18 C 0.4641(12) 0.7822(12) 0.0146(6) 0.098(4) Uani 1 1 d . . . . .
H18 H 0.4039 0.7413 -0.0374 0.117 Uiso 1 1 calc R U . . .
C19 C 0.5509(13) 0.8643(12) 0.0041(7) 0.096(4) Uani 1 1 d . . . . .
H19 H 0.5520 0.8797 -0.0550 0.116 Uiso 1 1 calc R U . . .
C20 C 0.6367(10) 0.9250(8) 0.0775(7) 0.074(3) Uani 1 1 d . . . . .
H20 H 0.6956 0.9836 0.0685 0.089 Uiso 1 1 calc R U . . .
C21 C 0.6415(7) 0.9044(6) 0.1659(5) 0.0526(17) Uani 1 1 d . . . . .
C22 C 0.393(5) 0.636(4) 0.126(4) 0.085(12) Uani 0.39(7) 1 d . . P A 1
H22 H 0.4014 0.6425 0.1929 0.103 Uiso 0.39(7) 1 calc R U P A 1
C23 C 0.437(5) 0.525(3) 0.087(3) 0.088(12) Uani 0.39(7) 1 d . . P A 1
H23A H 0.3941 0.4599 0.1054 0.131 Uiso 0.39(7) 1 calc R U P A 1
H23B H 0.5268 0.5306 0.1098 0.131 Uiso 0.39(7) 1 calc R U P A 1
H23C H 0.4173 0.5152 0.0201 0.131 Uiso 0.39(7) 1 calc R U P A 1
C24 C 0.255(4) 0.640(4) 0.076(4) 0.099(14) Uani 0.39(7) 1 d . . P A 1
H24A H 0.2462 0.6244 0.0102 0.149 Uiso 0.39(7) 1 calc R U P A 1
H24B H 0.2322 0.7155 0.0948 0.149 Uiso 0.39(7) 1 calc R U P A 1
H24C H 0.1993 0.5810 0.0932 0.149 Uiso 0.39(7) 1 calc R U P A 1
C22A C 0.360(3) 0.680(4) 0.1084(14) 0.092(13) Uani 0.61(7) 1 d . . P A 2
H22A H 0.3600 0.6910 0.1747 0.110 Uiso 0.61(7) 1 calc R U P A 2
C23A C 0.373(5) 0.558(4) 0.081(2) 0.119(13) Uani 0.61(7) 1 d . . P A 2
H23D H 0.3703 0.5419 0.0159 0.179 Uiso 0.61(7) 1 calc R U P A 2
H23E H 0.3042 0.5091 0.0939 0.179 Uiso 0.61(7) 1 calc R U P A 2
H23F H 0.4523 0.5426 0.1158 0.179 Uiso 0.61(7) 1 calc R U P A 2
C24A C 0.226(3) 0.706(5) 0.0584(18) 0.131(16) Uani 0.61(7) 1 d . . P A 2
H24D H 0.2289 0.7889 0.0603 0.196 Uiso 0.61(7) 1 calc R U P A 2
H24E H 0.1633 0.6788 0.0895 0.196 Uiso 0.61(7) 1 calc R U P A 2
H24F H 0.2055 0.6663 -0.0051 0.196 Uiso 0.61(7) 1 calc R U P A 2
C25 C 0.7375(8) 0.9714(6) 0.2472(6) 0.059(2) Uani 1 1 d . . . . .
H25 H 0.7074 0.9601 0.3030 0.071 Uiso 1 1 calc R U . . .
C26 C 0.8638(9) 0.9259(8) 0.2548(8) 0.079(3) Uani 1 1 d . . . . .
H26A H 0.8512 0.8427 0.2524 0.118 Uiso 1 1 calc R U . . .
H26B H 0.9205 0.9630 0.3128 0.118 Uiso 1 1 calc R U . . .
H26C H 0.8999 0.9431 0.2042 0.118 Uiso 1 1 calc R U . . .
C27 C 0.7570(11) 1.1008(7) 0.2471(9) 0.094(4) Uani 1 1 d . . . . .
H27A H 0.7755 1.1142 0.1892 0.142 Uiso 1 1 calc R U . . .
H27B H 0.8266 1.1383 0.2975 0.142 Uiso 1 1 calc R U . . .
H27C H 0.6812 1.1328 0.2545 0.142 Uiso 1 1 calc R U . . .
N1 N 0.6222(5) 0.6848(4) 0.3673(4) 0.0375(11) Uani 1 1 d . . . . .
N2 N 0.5627(5) 0.7830(4) 0.2633(4) 0.0393(11) Uani 1 1 d . . . . .
O101 O 0.8155(9) 0.5608(8) 0.2136(8) 0.131(4) Uani 1 1 d D . . . .
C101 C 0.8969(16) 0.5069(15) 0.2758(12) 0.151(7) Uani 1 1 d D . . . .
H10A H 0.9456 0.5654 0.3279 0.182 Uiso 1 1 calc R U . . .
H10B H 0.8472 0.4498 0.2996 0.182 Uiso 1 1 calc R U . . .
C102 C 0.9756(19) 0.4539(19) 0.2311(13) 0.174(9) Uani 1 1 d D . . . .
H10C H 0.9460 0.3705 0.2127 0.209 Uiso 1 1 calc R U . . .
H10D H 1.0606 0.4652 0.2706 0.209 Uiso 1 1 calc R U . . .
C103 C 0.9753(11) 0.5068(13) 0.1516(9) 0.121(5) Uani 1 1 d D . . . .
H10E H 0.9550 0.4474 0.0957 0.145 Uiso 1 1 calc R U . . .
H10F H 1.0581 0.5504 0.1565 0.145 Uiso 1 1 calc R U . . .
C104 C 0.8788(12) 0.5856(11) 0.1481(8) 0.106(4) Uani 1 1 d D . . . .
H10G H 0.9182 0.6668 0.1624 0.127 Uiso 1 1 calc R U . . .
H10H H 0.8216 0.5710 0.0871 0.127 Uiso 1 1 calc R U . . .
O201 O -0.110(3) 0.746(3) -0.0191(19) 0.318(10) Uani 1 1 d D U . . .
C201 C -0.028(3) 0.858(3) 0.005(2) 0.326(12) Uani 1 1 d D U . . .
H20A H -0.0771 0.9225 0.0003 0.391 Uiso 1 1 calc R U . . .
H20B H 0.0241 0.8689 0.0677 0.391 Uiso 1 1 calc R U . . .
C202 C 0.046(2) 0.851(3) -0.060(2) 0.258(11) Uani 1 1 d D U . . .
H20C H 0.0952 0.7866 -0.0579 0.309 Uiso 1 1 calc R U . . .
H20D H 0.1002 0.9240 -0.0564 0.309 Uiso 1 1 calc R U . . .
C203 C -0.061(2) 0.830(3) -0.1336(19) 0.240(9) Uani 1 1 d D U . . .
H20E H -0.0390 0.7987 -0.1911 0.288 Uiso 1 1 calc R U . . .
H20F H -0.0963 0.9018 -0.1409 0.288 Uiso 1 1 calc R U . . .
C204 C -0.154(2) 0.745(2) -0.112(2) 0.231(9) Uani 1 1 d D U . . .
H20G H -0.2383 0.7681 -0.1248 0.277 Uiso 1 1 calc R U . . .
H20H H -0.1576 0.6675 -0.1482 0.277 Uiso 1 1 calc R U . . .
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'
O O 0.0106 0.0060 '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'
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_3
C3 Bi1 Br3 97.05(16) .
C3 Bi1 Br1 90.21(16) .
Br3 Bi1 Br1 96.09(5) .
C3 Bi1 Br2 83.07(16) .
Br3 Bi1 Br2 94.70(4) .
Br1 Bi1 Br2 167.92(3) .
C3 Bi1 Br2 89.99(16) 2_676
Br3 Bi1 Br2 171.84(3) 2_676
Br1 Bi1 Br2 87.97(4) 2_676
Br2 Bi1 Br2 82.03(3) 2_676
Bi1 Br2 Bi1 97.97(3) 2_676
N2 C1 N1 108.8(5) .
N2 C1 H1 125.6 .
N1 C1 H1 125.6 .
C3 C2 N1 108.1(5) .
C3 C2 H2 125.9 .
N1 C2 H2 125.9 .
C2 C3 N2 104.6(5) .
C2 C3 Bi1 120.4(4) .
N2 C3 Bi1 134.8(4) .
C9 C4 C5 125.1(6) .
C9 C4 N1 117.9(6) .
C5 C4 N1 117.0(7) .
C6 C5 C4 115.2(8) .
C6 C5 C10 121.6(7) .
C4 C5 C10 123.2(6) .
C7 C6 C5 122.1(8) .
C7 C6 H6 119.0 .
C5 C6 H6 118.9 .
C6 C7 C8 120.4(8) .
C6 C7 H7 119.8 .
C8 C7 H7 119.8 .
C7 C8 C9 121.4(9) .
C7 C8 H8 119.3 .
C9 C8 H8 119.3 .
C4 C9 C8 115.8(7) .
C4 C9 C13 123.7(6) .
C8 C9 C13 120.5(8) .
C5 C10 C12 111.5(7) .
C5 C10 C11 110.3(8) .
C12 C10 C11 109.3(7) .
C5 C10 H10 108.6 .
C12 C10 H10 108.6 .
C11 C10 H10 108.6 .
C10 C11 H11A 109.5 .
C10 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
C10 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
C10 C12 H12A 109.5 .
C10 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C10 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C14 C13 C9 112.3(7) .
C14 C13 C15 110.5(7) .
C9 C13 C15 111.6(7) .
C14 C13 H13 107.4 .
C9 C13 H13 107.4 .
C15 C13 H13 107.4 .
C13 C14 H14A 109.5 .
C13 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C13 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
C13 C15 H15A 109.5 .
C13 C15 H15B 109.5 .
H15A C15 H15B 109.5 .
C13 C15 H15C 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
C21 C16 C17 123.4(7) .
C21 C16 N2 118.9(7) .
C17 C16 N2 117.7(7) .
C16 C17 C22A 125.5(12) .
C16 C17 C18 116.4(10) .
C22A C17 C18 117.9(14) .
C16 C17 C22 112(2) .
C18 C17 C22 128(2) .
C19 C18 C17 121.2(11) .
C19 C18 H18 119.4 .
C17 C18 H18 119.4 .
C18 C19 C20 120.4(9) .
C18 C19 H19 119.8 .
C20 C19 H19 119.8 .
C19 C20 C21 122.3(9) .
C19 C20 H20 118.8 .
C21 C20 H20 118.8 .
C16 C21 C20 116.1(8) .
C16 C21 C25 121.7(6) .
C20 C21 C25 122.2(7) .
C23 C22 C24 110(3) .
C23 C22 C17 115(3) .
C24 C22 C17 99(3) .
C23 C22 H22 110.7 .
C24 C22 H22 110.7 .
C17 C22 H22 110.7 .
C22 C23 H23A 109.5 .
C22 C23 H23B 109.5 .
H23A C23 H23B 109.5 .
C22 C23 H23C 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
C22 C24 H24A 109.5 .
C22 C24 H24B 109.5 .
H24A C24 H24B 109.5 .
C22 C24 H24C 109.5 .
H24A C24 H24C 109.5 .
H24B C24 H24C 109.5 .
C17 C22A C23A 113(2) .
C17 C22A C24A 115(3) .
C23A C22A C24A 111(2) .
C17 C22A H22A 105.8 .
C23A C22A H22A 105.8 .
C24A C22A H22A 105.8 .
C22A C23A H23D 109.5 .
C22A C23A H23E 109.5 .
H23D C23A H23E 109.5 .
C22A C23A H23F 109.5 .
H23D C23A H23F 109.5 .
H23E C23A H23F 109.5 .
C22A C24A H24D 109.5 .
C22A C24A H24E 109.5 .
H24D C24A H24E 109.5 .
C22A C24A H24F 109.5 .
H24D C24A H24F 109.5 .
H24E C24A H24F 109.5 .
C21 C25 C27 113.4(8) .
C21 C25 C26 111.3(7) .
C27 C25 C26 109.3(7) .
C21 C25 H25 107.5 .
C27 C25 H25 107.5 .
C26 C25 H25 107.5 .
C25 C26 H26A 109.5 .
C25 C26 H26B 109.5 .
H26A C26 H26B 109.5 .
C25 C26 H26C 109.5 .
H26A C26 H26C 109.5 .
H26B C26 H26C 109.5 .
C25 C27 H27A 109.5 .
C25 C27 H27B 109.5 .
H27A C27 H27B 109.5 .
C25 C27 H27C 109.5 .
H27A C27 H27C 109.5 .
H27B C27 H27C 109.5 .
C1 N1 C2 108.2(5) .
C1 N1 C4 126.0(5) .
C2 N1 C4 125.8(5) .
C1 N2 C3 110.3(5) .
C1 N2 C16 119.4(5) .
C3 N2 C16 130.2(5) .
C104 O101 C101 106.6(9) .
C102 C101 O101 109.3(12) .
C102 C101 H10A 109.8 .
O101 C101 H10A 109.8 .
C102 C101 H10B 109.8 .
O101 C101 H10B 109.8 .
H10A C101 H10B 108.3 .
C101 C102 C103 105.8(12) .
C101 C102 H10C 110.6 .
C103 C102 H10C 110.6 .
C101 C102 H10D 110.6 .
C103 C102 H10D 110.6 .
H10C C102 H10D 108.7 .
C102 C103 C104 107.1(10) .
C102 C103 H10E 110.3 .
C104 C103 H10E 110.3 .
C102 C103 H10F 110.3 .
C104 C103 H10F 110.3 .
H10E C103 H10F 108.6 .
O101 C104 C103 104.9(11) .
O101 C104 H10G 110.8 .
C103 C104 H10G 110.8 .
O101 C104 H10H 110.8 .
C103 C104 H10H 110.8 .
H10G C104 H10H 108.8 .
C204 O201 C201 98.9(18) .
C202 C201 O201 104(2) .
C202 C201 H20A 111.0 .
O201 C201 H20A 111.0 .
C202 C201 H20B 111.0 .
O201 C201 H20B 111.0 .
H20A C201 H20B 109.0 .
C201 C202 C203 91.8(18) .
C201 C202 H20C 113.3 .
C203 C202 H20C 113.3 .
C201 C202 H20D 113.3 .
C203 C202 H20D 113.3 .
H20C C202 H20D 110.7 .
C202 C203 C204 107.5(18) .
C202 C203 H20E 110.2 .
C204 C203 H20E 110.2 .
C202 C203 H20F 110.2 .
C204 C203 H20F 110.2 .
H20E C203 H20F 108.5 .
O201 C204 C203 103.7(17) .
O201 C204 H20G 111.0 .
C203 C204 H20G 111.0 .
O201 C204 H20H 111.0 .
C203 C204 H20H 111.0 .
H20G C204 H20H 109.0 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 C3 2.277(6) .
Bi1 Br3 2.6763(11) .
Bi1 Br1 2.7055(14) .
Bi1 Br2 3.0299(15) .
Bi1 Br2 3.0723(10) 2_676
Br2 Bi1 3.0723(10) 2_676
C1 N2 1.312(8) .
C1 N1 1.329(8) .
C1 H1 0.9500 .
C2 C3 1.362(9) .
C2 N1 1.387(7) .
C2 H2 0.9500 .
C3 N2 1.399(7) .
C4 C9 1.379(11) .
C4 C5 1.412(9) .
C4 N1 1.455(8) .
C5 C6 1.397(11) .
C5 C10 1.509(12) .
C6 C7 1.361(14) .
C6 H6 0.9500 .
C7 C8 1.385(12) .
C7 H7 0.9500 .
C8 C9 1.402(10) .
C8 H8 0.9500 .
C9 C13 1.513(10) .
C10 C12 1.523(11) .
C10 C11 1.531(11) .
C10 H10 1.0000 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.511(10) .
C13 C15 1.530(14) .
C13 H13 1.0000 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C21 1.382(10) .
C16 C17 1.398(13) .
C16 N2 1.463(8) .
C17 C22A 1.40(3) .
C17 C18 1.411(14) .
C17 C22 1.68(5) .
C18 C19 1.351(17) .
C18 H18 0.9500 .
C19 C20 1.357(16) .
C19 H19 0.9500 .
C20 C21 1.399(11) .
C20 H20 0.9500 .
C21 C25 1.507(12) .
C22 C23 1.53(5) .
C22 C24 1.57(5) .
C22 H22 1.0000 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C22A C23A 1.48(4) .
C22A C24A 1.60(3) .
C22A H22A 1.0000 .
C23A H23D 0.9800 .
C23A H23E 0.9800 .
C23A H23F 0.9800 .
C24A H24D 0.9800 .
C24A H24E 0.9800 .
C24A H24F 0.9800 .
C25 C27 1.533(10) .
C25 C26 1.545(11) .
C25 H25 1.0000 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
O101 C104 1.387(13) .
O101 C101 1.441(16) .
C101 C102 1.365(16) .
C101 H10A 0.9900 .
C101 H10B 0.9900 .
C102 C103 1.449(19) .
C102 H10C 0.9900 .
C102 H10D 0.9900 .
C103 C104 1.495(16) .
C103 H10E 0.9900 .
C103 H10F 0.9900 .
C104 H10G 0.9900 .
C104 H10H 0.9900 .
O201 C204 1.40(2) .
O201 C201 1.48(2) .
C201 C202 1.41(2) .
C201 H20A 0.9900 .
C201 H20B 0.9900 .
C202 C203 1.43(2) .
C202 H20C 0.9900 .
C202 H20D 0.9900 .
C203 C204 1.49(2) .
C203 H20E 0.9900 .
C203 H20F 0.9900 .
C204 H20G 0.9900 .
C204 H20H 0.9900 .
