#------------------------------------------------------------------------------
#$Date: 2019-10-28 17:40:17 +0200 (Mon, 28 Oct 2019) $
#$Revision: 220149 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/50/4515005.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_4515005
loop_
_publ_author_name
'Li, Yuan-Yuan'
'Wang, Fu-Rong'
'Li, Zi-Yan'
'Yan, Zhen-Ning'
'Niu, Yun-Yin'
_publ_section_title
;
 Assembly and Adsorption Properties of Seven Supramolecular Compounds with
 Heteromacrocycle Imidazolium.
;
_journal_issue                   5
_journal_name_full               'ACS omega'
_journal_page_first              8926
_journal_page_last               8934
_journal_paper_doi               10.1021/acsomega.9b00669
_journal_volume                  4
_journal_year                    2019
_chemical_formula_moiety         'Bi2 I10, C36 H44 N8'
_chemical_formula_sum            'C36 H44 Bi2 I10 N8'
_chemical_formula_weight         2275.75
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                106.012(7)
_cell_angle_beta                 102.632(6)
_cell_angle_gamma                104.851(6)
_cell_formula_units_Z            1
_cell_length_a                   9.9688(6)
_cell_length_b                   11.3087(8)
_cell_length_c                   14.0156(11)
_cell_measurement_reflns_used    2417
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.6750
_cell_measurement_theta_min      3.6140
_cell_volume                     1395.0(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -99.0000 -134.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   24.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -99.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   37.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega  -46.00  -19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -57.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega   10.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -57.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   -9.00   82.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   77.0000 -150.0000 91

#__ type_ start__ end____ width___ exp.time_
  7 omega  -47.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -57.0000  -30.0000 81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0761561000
_diffrn_orient_matrix_UB_12      0.0156348000
_diffrn_orient_matrix_UB_13      0.0080387000
_diffrn_orient_matrix_UB_21      -0.0141699000
_diffrn_orient_matrix_UB_22      -0.0422885000
_diffrn_orient_matrix_UB_23      -0.0516974000
_diffrn_orient_matrix_UB_31      0.0004339000
_diffrn_orient_matrix_UB_32      0.0526577000
_diffrn_orient_matrix_UB_33      -0.0182382000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12287
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.347
_diffrn_reflns_theta_min         3.629
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    11.864
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.709
_exptl_crystal_description       prism
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.189
_refine_diff_density_min         -1.110
_refine_diff_density_rms         0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         6465
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0526
_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)+(0.0297P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.1091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3885
_reflns_number_total             6465
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao9b00669_si_002.cif
_cod_data_source_block           5
_cod_original_cell_volume        1394.98(18)
_cod_database_code               4515005
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C38H70N2O12FI2Bi1
_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.
;
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 C12A-N4A
 1.4 with sigma of 0.02
 C12-C13
 1.4 with sigma of 0.02
 C14-C13
 2.2 with sigma of 0.02
 C18-C17A
 1.55 with sigma of 0.02
 C18-C17
 1.55 with sigma of 0.02
 C17A-C16A
 1.55 with sigma of 0.02
 C16A-C15A
 1.55 with sigma of 0.02
 C16-C17
 1.55 with sigma of 0.02
 C14A-N4A
 1.39 with sigma of 0.02
 C12-N4
 1.39 with sigma of 0.02
3. Rigid bond restraints
 C15A, C16A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C15A) \\sim Ueq, Uanis(C16A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N4) = Uanis(N4A)
Uanis(C12) = Uanis(C12A)
Uanis(C13) = Uanis(C13A)
Uanis(C14) = Uanis(C14A)
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
Uanis(C17) = Uanis(C17A)
5. Others
 Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(C17A)=Sof(H17C)=
 Sof(H17D)=Sof(H18C)=Sof(H18D)=Sof(N4A)=1-FVAR(1)
 Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15A)=
 Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H18A)=
 Sof(H18B)=Sof(N4)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B), C15(H15A,H15B), C15A(H15C,H15D), C16(H16A,H16B),
 C16A(H16C,H16D), C17(H17A,H17B), C17A(H17C,H17D), C18(H18A,H18B), C18(H18C,
 H18D)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C8(H8), C9(H9), C10(H10), C12(H12),
 C12A(H12A), C13(H13), C13A(H13A), C14(H14), C14A(H14A)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.00162(4) 0.52446(3) 0.17467(3) 0.05060(14) Uani 1 1 d . . . . .
I1 I 0.07965(8) 0.82257(6) 0.24176(7) 0.0784(3) Uani 1 1 d . . . . .
I2 I 0.26384(9) 0.57707(8) 0.35775(7) 0.0840(3) Uani 1 1 d . . . . .
I3 I 0.22581(6) 0.50863(6) 0.03305(6) 0.0552(2) Uani 1 1 d . . . . .
I4 I -0.08100(8) 0.22547(6) 0.11740(7) 0.0700(2) Uani 1 1 d . . . . .
I5 I -0.21402(10) 0.50975(8) 0.28831(8) 0.0962(3) Uani 1 1 d . . . . .
C1 C 1.221(2) 1.1823(14) 0.5032(13) 0.110(6) Uani 1 1 d . . . . .
H1 H 1.2920 1.1561 0.5385 0.132 Uiso 1 1 calc R . . . .
C2 C 1.085(2) 1.1622(13) 0.5093(12) 0.106(5) Uani 1 1 d . . . . .
H2 H 1.0450 1.1231 0.5515 0.127 Uiso 1 1 calc R . . . .
C3 C 1.1130(12) 1.2640(9) 0.3992(9) 0.060(3) Uani 1 1 d . . . . .
H3 H 1.0967 1.3061 0.3516 0.072 Uiso 1 1 calc R . . . .
C4 C 0.8668(14) 1.2152(10) 0.4176(12) 0.091(5) Uani 1 1 d . . . . .
H4A H 0.8537 1.2632 0.3707 0.109 Uiso 1 1 calc R . . . .
H4B H 0.8541 1.2624 0.4823 0.109 Uiso 1 1 calc R . . . .
C5 C 0.7503(12) 1.0820(9) 0.3696(10) 0.063(3) Uani 1 1 d . . . . .
C6 C 0.7542(11) 0.9871(10) 0.2856(10) 0.067(3) Uani 1 1 d . . . . .
H6 H 0.8328 1.0034 0.2598 0.080 Uiso 1 1 calc R . . . .
C7 C 0.6440(11) 0.8687(9) 0.2393(9) 0.057(3) Uani 1 1 d . . . . .
C8 C 0.5254(11) 0.8477(12) 0.2749(10) 0.069(3) Uani 1 1 d . . . . .
H8 H 0.4465 0.7703 0.2411 0.082 Uiso 1 1 calc R . . . .
C9 C 0.5240(12) 0.9429(13) 0.3617(11) 0.073(3) Uani 1 1 d . . . . .
H9 H 0.4457 0.9267 0.3878 0.088 Uiso 1 1 calc R . . . .
C10 C 0.6344(12) 1.0587(11) 0.4088(10) 0.069(3) Uani 1 1 d . . . . .
H10 H 0.6323 1.1217 0.4668 0.082 Uiso 1 1 calc R . . . .
C11 C 0.6454(11) 0.7621(10) 0.1461(10) 0.065(3) Uani 1 1 d . . . . .
H11A H 0.7354 0.7432 0.1639 0.078 Uiso 1 1 calc R . . . .
H11B H 0.5647 0.6830 0.1305 0.078 Uiso 1 1 calc R . . . .
C12 C 0.730(3) 0.876(3) -0.058(2) 0.072(7) Uani 0.476(8) 1 d D . P A 1
H12 H 0.7938 0.9144 -0.0898 0.086 Uiso 0.476(8) 1 calc R . P A 1
C12A C 0.518(3) 0.865(2) -0.0650(19) 0.072(7) Uani 0.524(8) 1 d D . P A 2
H12A H 0.4478 0.8819 -0.1099 0.086 Uiso 0.524(8) 1 calc R . P A 2
C13 C 0.762(3) 0.851(4) 0.033(3) 0.066(6) Uani 0.476(8) 1 d D . P A 1
H13 H 0.8553 0.8654 0.0747 0.080 Uiso 0.476(8) 1 calc R . P A 1
C13A C 0.496(3) 0.824(2) 0.013(2) 0.066(6) Uani 0.524(8) 1 d . . P A 2
H13A H 0.4155 0.8136 0.0370 0.080 Uiso 0.524(8) 1 calc R . P A 2
C14 C 0.522(3) 0.778(2) -0.029(2) 0.071(6) Uani 0.476(8) 1 d D . P A 1
H14 H 0.4240 0.7342 -0.0405 0.085 Uiso 0.476(8) 1 calc R . P A 1
C14A C 0.724(4) 0.844(3) 0.005(3) 0.071(6) Uani 0.524(8) 1 d D . P A 2
H14A H 0.8212 0.8494 0.0227 0.085 Uiso 0.524(8) 1 calc R . P A 2
C15 C 0.496(3) 0.833(3) -0.192(2) 0.094(5) Uani 0.476(8) 1 d . . P A 1
H15A H 0.5260 0.9226 -0.1908 0.113 Uiso 0.476(8) 1 calc R . P A 1
H15B H 0.3934 0.8090 -0.1959 0.113 Uiso 0.476(8) 1 calc R . P A 1
C15A C 0.748(3) 0.934(2) -0.127(2) 0.094(5) Uani 0.524(8) 1 d D U P A 2
H15C H 0.8395 0.9174 -0.1123 0.113 Uiso 0.524(8) 1 calc R . P A 2
H15D H 0.7700 1.0283 -0.1044 0.113 Uiso 0.524(8) 1 calc R . P A 2
C16 C 0.507(3) 0.746(2) -0.292(3) 0.095(5) Uani 0.476(8) 1 d D . P A 1
H16A H 0.4302 0.7380 -0.3517 0.114 Uiso 0.476(8) 1 calc R . P A 1
H16B H 0.4962 0.6593 -0.2893 0.114 Uiso 0.476(8) 1 calc R . P A 1
C16A C 0.669(3) 0.8742(19) -0.245(2) 0.095(5) Uani 0.524(8) 1 d D U P A 2
H16C H 0.5771 0.8907 -0.2574 0.114 Uiso 0.524(8) 1 calc R . P A 2
H16D H 0.7273 0.9200 -0.2789 0.114 Uiso 0.524(8) 1 calc R . P A 2
C17 C 0.656(3) 0.804(2) -0.3047(19) 0.082(7) Uani 0.476(8) 1 d D . P A 1
H17A H 0.6737 0.8930 -0.3034 0.099 Uiso 0.476(8) 1 calc R . P A 1
H17B H 0.7352 0.8009 -0.2524 0.099 Uiso 0.476(8) 1 calc R . P A 1
C17A C 0.638(3) 0.7321(17) -0.2955(17) 0.082(7) Uani 0.524(8) 1 d D . P A 2
H17C H 0.5454 0.6824 -0.2912 0.099 Uiso 0.524(8) 1 calc R . P A 2
H17D H 0.7142 0.7053 -0.2616 0.099 Uiso 0.524(8) 1 calc R . P A 2
C18 C 0.6299(13) 0.7088(15) -0.4130(11) 0.113(6) Uani 1 1 d D . . . .
H18A H 0.6113 0.6204 -0.4127 0.136 Uiso 0.476(8) 1 calc R . P A 1
H18B H 0.5474 0.7107 -0.4634 0.136 Uiso 0.476(8) 1 calc R . P A 1
H18C H 0.5853 0.6156 -0.4514 0.136 Uiso 0.524(8) 1 calc R . P A 2
H18D H 0.5640 0.7502 -0.4401 0.136 Uiso 0.524(8) 1 calc R . P A 2
N1 N 1.2372(12) 1.2467(9) 0.4373(9) 0.081(3) Uani 1 1 d . . . . .
N2 N 1.0165(11) 1.2117(7) 0.4397(8) 0.064(3) Uani 1 1 d . . . . .
N3 N 0.6337(10) 0.7995(8) 0.0528(8) 0.070(3) Uani 1 1 d . . . . .
N4 N 0.582(3) 0.831(2) -0.090(3) 0.070(6) Uani 0.476(8) 1 d D . P A 1
N4A N 0.660(2) 0.881(2) -0.072(2) 0.070(6) Uani 0.524(8) 1 d D . P A 2
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'
Bi Bi -4.1077 10.2566 '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'
N N 0.0061 0.0033 '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_1
_geom_angle_site_symmetry_3
I1 Bi1 I3 94.84(2) . .
I1 Bi1 I3 89.78(2) . 2_565
I1 Bi1 I4 177.11(3) . .
I2 Bi1 I1 86.55(3) . .
I2 Bi1 I3 85.68(2) . .
I2 Bi1 I3 169.27(3) . 2_565
I2 Bi1 I4 92.37(2) . .
I3 Bi1 I3 84.58(2) 2_565 .
I4 Bi1 I3 87.75(2) . .
I4 Bi1 I3 91.74(2) . 2_565
I5 Bi1 I1 90.70(3) . .
I5 Bi1 I2 96.70(3) . .
I5 Bi1 I3 174.09(2) . .
I5 Bi1 I3 93.43(3) . 2_565
I5 Bi1 I4 86.75(3) . .
Bi1 I3 Bi1 95.42(2) 2_565 .
C2 C1 H1 126.1 . .
N1 C1 H1 126.1 . .
N1 C1 C2 107.8(15) . .
C1 C2 H2 126.9 . .
C1 C2 N2 106.3(15) . .
N2 C2 H2 126.9 . .
N1 C3 H3 125.7 . .
N2 C3 H3 125.7 . .
N2 C3 N1 108.7(11) . .
H4A C4 H4B 107.7 . .
C5 C4 H4A 108.8 . .
C5 C4 H4B 108.8 . .
N2 C4 H4A 108.8 . .
N2 C4 H4B 108.8 . .
N2 C4 C5 114.0(8) . .
C6 C5 C4 121.4(10) . .
C6 C5 C10 120.1(10) . .
C10 C5 C4 118.5(11) . .
C5 C6 H6 119.6 . .
C7 C6 C5 120.9(10) . .
C7 C6 H6 119.6 . .
C6 C7 C8 119.1(11) . .
C6 C7 C11 122.0(10) . .
C8 C7 C11 118.8(10) . .
C7 C8 H8 120.2 . .
C7 C8 C9 119.6(11) . .
C9 C8 H8 120.2 . .
C8 C9 H9 119.4 . .
C10 C9 C8 121.2(11) . .
C10 C9 H9 119.4 . .
C5 C10 H10 120.5 . .
C9 C10 C5 119.1(12) . .
C9 C10 H10 120.5 . .
C7 C11 H11A 109.2 . .
C7 C11 H11B 109.2 . .
H11A C11 H11B 107.9 . .
N3 C11 C7 112.2(8) . .
N3 C11 H11A 109.2 . .
N3 C11 H11B 109.2 . .
C13 C12 H12 129.3 . .
N4 C12 H12 129.3 . .
N4 C12 C13 101(2) . .
C13A C12A H12A 123.8 . .
C13A C12A N4A 112(2) . .
N4A C12A H12A 123.8 . .
C12 C13 H13 125.2 . .
C12 C13 N3 110(2) . .
N3 C13 H13 125.2 . .
C12A C13A H13A 128.6 . .
C12A C13A N3 103(2) . .
N3 C13A H13A 128.6 . .
N3 C14 H14 127.5 . .
N3 C14 N4 105(2) . .
N4 C14 H14 127.5 . .
N3 C14A H14A 123.6 . .
N3 C14A N4A 113(3) . .
N4A C14A H14A 123.6 . .
H15A C15 H15B 107.2 . .
C16 C15 H15A 108.0 . .
C16 C15 H15B 108.0 . .
N4 C15 H15A 108.0 . .
N4 C15 H15B 108.0 . .
N4 C15 C16 117(2) . .
H15C C15A H15D 108.1 . .
C16A C15A H15C 109.5 . .
C16A C15A H15D 109.5 . .
N4A C15A H15C 109.5 . .
N4A C15A H15D 109.5 . .
N4A C15A C16A 111(2) . .
C15 C16 H16A 109.7 . .
C15 C16 H16B 109.7 . .
C15 C16 C17 110(2) . .
H16A C16 H16B 108.2 . .
C17 C16 H16A 109.7 . .
C17 C16 H16B 109.7 . .
C15A C16A H16C 108.0 . .
C15A C16A H16D 108.0 . .
H16C C16A H16D 107.2 . .
C17A C16A C15A 117(2) . .
C17A C16A H16C 108.0 . .
C17A C16A H16D 108.0 . .
C16 C17 H17A 112.1 . .
C16 C17 H17B 112.1 . .
H17A C17 H17B 109.7 . .
C18 C17 C16 98.3(18) . .
C18 C17 H17A 112.1 . .
C18 C17 H17B 112.1 . .
C16A C17A H17C 110.4 . .
C16A C17A H17D 110.4 . .
C16A C17A C18 106.4(17) . .
H17C C17A H17D 108.6 . .
C18 C17A H17C 110.4 . .
C18 C17A H17D 110.4 . .
C17 C18 H18A 110.8 . .
C17 C18 H18B 110.8 . .
C17A C18 H18C 107.5 . .
C17A C18 H18D 107.5 . .
H18A C18 H18B 108.8 . .
H18C C18 H18D 107.0 . .
N1 C18 C17 104.9(13) 2_775 .
N1 C18 C17A 119.1(13) 2_775 .
N1 C18 H18A 110.8 2_775 .
N1 C18 H18B 110.8 2_775 .
N1 C18 H18C 107.5 2_775 .
N1 C18 H18D 107.5 2_775 .
C1 N1 C18 124.8(13) . 2_775
C3 N1 C1 109.5(13) . .
C3 N1 C18 125.7(13) . 2_775
C2 N2 C4 128.0(13) . .
C3 N2 C2 107.7(12) . .
C3 N2 C4 124.2(10) . .
C11 N3 C13A 114.9(13) . .
C13 N3 C11 117.4(13) . .
C14 N3 C11 133.0(15) . .
C14 N3 C13 108.7(18) . .
C14A N3 C11 136.3(14) . .
C14A N3 C13A 107.0(19) . .
C12 N4 C15 121(3) . .
C14 N4 C12 115(3) . .
C14 N4 C15 124(2) . .
C12A N4A C15A 137(2) . .
C14A N4A C12A 104(3) . .
C14A N4A C15A 118(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 I1 3.0727(8) .
Bi1 I2 3.0328(9) .
Bi1 I3 3.3039(9) .
Bi1 I3 3.1358(8) 2_565
Bi1 I4 3.0889(7) .
Bi1 I5 2.9404(10) .
I3 Bi1 3.1358(8) 2_565
C1 H1 0.9300 .
C1 C2 1.34(2) .
C1 N1 1.335(19) .
C2 H2 0.9300 .
C2 N2 1.393(16) .
C3 H3 0.9300 .
C3 N1 1.322(12) .
C3 N2 1.315(13) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C4 C5 1.508(14) .
C4 N2 1.469(13) .
C5 C6 1.373(14) .
C5 C10 1.381(14) .
C6 H6 0.9300 .
C6 C7 1.370(13) .
C7 C8 1.372(14) .
C7 C11 1.519(15) .
C8 H8 0.9300 .
C8 C9 1.390(15) .
C9 H9 0.9300 .
C9 C10 1.352(14) .
C10 H10 0.9300 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 N3 1.472(14) .
C12 H12 0.9300 .
C12 C13 1.377(19) .
C12 N4 1.363(18) .
C12A H12A 0.9300 .
C12A C13A 1.35(4) .
C12A N4A 1.400(18) .
C13 H13 0.9300 .
C13 N3 1.38(4) .
C13A H13A 0.9300 .
C13A N3 1.48(3) .
C14 H14 0.9300 .
C14 N3 1.32(3) .
C14 N4 1.34(4) .
C14A H14A 0.9300 .
C14A N3 1.31(4) .
C14A N4A 1.352(18) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 C16 1.52(4) .
C15 N4 1.51(4) .
C15A H15C 0.9700 .
C15A H15D 0.9700 .
C15A C16A 1.526(18) .
C15A N4A 1.43(3) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C16 C17 1.526(18) .
C16A H16C 0.9700 .
C16A H16D 0.9700 .
C16A C17A 1.483(16) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 C18 1.520(17) .
C17A H17C 0.9700 .
C17A H17D 0.9700 .
C17A C18 1.576(17) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C18 H18C 0.9700 .
C18 H18D 0.9700 .
C18 N1 1.441(16) 2_775
N1 C18 1.441(16) 2_775
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_4
C1 C2 N2 C3 -2.9(15) .
C1 C2 N2 C4 -179.3(12) .
C2 C1 N1 C3 -2.0(17) .
C2 C1 N1 C18 177.4(12) 2_775
C4 C5 C6 C7 -176.7(10) .
C4 C5 C10 C9 175.3(10) .
C5 C4 N2 C2 -64.0(17) .
C5 C4 N2 C3 120.2(12) .
C5 C6 C7 C8 2.9(16) .
C5 C6 C7 C11 179.9(10) .
C6 C5 C10 C9 -1.7(17) .
C6 C7 C8 C9 -4.6(16) .
C6 C7 C11 N3 -65.7(13) .
C7 C8 C9 C10 3.2(17) .
C7 C11 N3 C13 96(3) .
C7 C11 N3 C13A -62.0(14) .
C7 C11 N3 C14 -96(2) .
C7 C11 N3 C14A 100(3) .
C8 C7 C11 N3 111.3(11) .
C8 C9 C10 C5 0.0(17) .
C10 C5 C6 C7 0.2(17) .
C11 C7 C8 C9 178.3(9) .
C12 C13 N3 C11 178(2) .
C12 C13 N3 C14 7(4) .
C12A C13A N3 C11 175.4(14) .
C12A C13A N3 C14A 8(3) .
C13 C12 N4 C14 -2(4) .
C13 C12 N4 C15 -177(3) .
C13A C12A N4A C14A 1(3) .
C13A C12A N4A C15A -171(3) .
C15 C16 C17 C18 -174(2) .
C15A C16A C17A C18 -153(2) .
C16 C15 N4 C12 66(3) .
C16 C15 N4 C14 -109(3) .
C16 C17 C18 N1 179.0(18) 2_775
C16A C15A N4A C12A -54(4) .
C16A C15A N4A C14A 134(3) .
C16A C17A C18 N1 72(2) 2_775
N1 C1 C2 N2 3.0(17) .
N1 C3 N2 C2 1.7(12) .
N1 C3 N2 C4 178.2(9) .
N2 C3 N1 C1 0.1(14) .
N2 C3 N1 C18 -179.3(11) 2_775
N2 C4 C5 C6 -48.9(17) .
N2 C4 C5 C10 134.1(11) .
N3 C14 N4 C12 7(3) .
N3 C14 N4 C15 -179(2) .
N3 C14A N4A C12A 4(4) .
N3 C14A N4A C15A 178(2) .
N4 C12 C13 N3 -3(4) .
N4 C14 N3 C11 -177.0(16) .
N4 C14 N3 C13 -8(3) .
N4 C15 C16 C17 -74(3) .
N4A C12A C13A N3 -6(3) .
N4A C14A N3 C11 -171.1(17) .
N4A C14A N3 C13A -8(4) .
N4A C15A C16A C17A -64(3) .
