#------------------------------------------------------------------------------
#$Date: 2019-10-28 17:40:17 +0200 (Mon, 28 Oct 2019) $
#$Revision: 220149 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/50/4515006.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_4515006
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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-05-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.216(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.4446(6)
_cell_length_b                   22.4097(10)
_cell_length_c                   12.5907(7)
_cell_measurement_reflns_used    2853
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5810
_cell_measurement_theta_min      3.7410
_cell_volume                     2687.7(3)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -53.00  -20.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -57.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega   -3.00   23.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -99.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -45.00   45.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -77.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega    3.00   70.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   57.0000  -30.0000 67
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0129783000
_diffrn_orient_matrix_UB_12      -0.0227181000
_diffrn_orient_matrix_UB_13      0.0335341000
_diffrn_orient_matrix_UB_21      0.0188830000
_diffrn_orient_matrix_UB_22      -0.0219437000
_diffrn_orient_matrix_UB_23      -0.0315841000
_diffrn_orient_matrix_UB_31      0.0708740000
_diffrn_orient_matrix_UB_32      0.0016967000
_diffrn_orient_matrix_UB_33      0.0411713000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11395
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.415
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    12.315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24506
_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    2.812
_exptl_crystal_description       plate
_exptl_crystal_F_000             2024
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.992
_refine_diff_density_min         -1.568
_refine_diff_density_rms         0.228
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0523
_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)+(0.0394P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3964
_reflns_number_total             5473
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao9b00669_si_002.cif
_cod_data_source_block           6
_cod_database_code               4515006
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C38H70N2O2I2Bi1
_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 99.72
_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
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16),
 C17(H17)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Bi1 Bi 0.13820(4) 0.41175(2) 0.03932(3) 0.03632(13) Uani 1 1 d .
I1 I 0.08648(8) 0.28941(4) 0.10361(7) 0.0579(2) Uani 1 1 d .
I2 I 0.26517(8) 0.44103(5) 0.29369(6) 0.0594(3) Uani 1 1 d .
I3 I -0.16518(6) 0.44902(3) 0.01597(6) 0.04045(19) Uani 1 1 d .
I4 I 0.43495(7) 0.39971(4) 0.05703(7) 0.0589(3) Uani 1 1 d .
I5 I 0.02667(9) 0.37769(5) -0.22737(7) 0.0638(3) Uani 1 1 d .
C1 C 0.5644(12) 0.3850(6) 0.6310(10) 0.056(3) Uani 1 1 d .
H1 H 0.6425 0.4097 0.6627 0.067 Uiso 1 1 calc R
C2 C 0.5589(11) 0.3425(6) 0.5495(10) 0.051(3) Uani 1 1 d .
H2 H 0.6345 0.3386 0.5290 0.062 Uiso 1 1 calc R
C3 C 0.4449(10) 0.3061(6) 0.4985(9) 0.045(3) Uani 1 1 d .
C4 C 0.3392(12) 0.3104(7) 0.5368(12) 0.063(4) Uani 1 1 d .
H4 H 0.2614 0.2855 0.5049 0.076 Uiso 1 1 calc R
C5 C 0.3462(13) 0.3509(8) 0.6213(13) 0.075(4) Uani 1 1 d .
H5 H 0.2762 0.3511 0.6489 0.090 Uiso 1 1 calc R
C6 C 0.4562(12) 0.3914(6) 0.6661(10) 0.052(3) Uani 1 1 d .
C7 C 0.4510(13) 0.4391(6) 0.7441(9) 0.060(4) Uani 1 1 d .
H7A H 0.5425 0.4579 0.7807 0.072 Uiso 1 1 calc R
H7B H 0.4279 0.4222 0.8050 0.072 Uiso 1 1 calc R
C8 C 0.3385(13) 0.5121(6) 0.5788(10) 0.060(4) Uani 1 1 d .
H8 H 0.4012 0.5071 0.5442 0.072 Uiso 1 1 calc R
C9 C 0.2245(13) 0.5475(6) 0.5412(10) 0.061(4) Uani 1 1 d .
H9 H 0.1916 0.5704 0.4736 0.073 Uiso 1 1 calc R
C10 C 0.2381(13) 0.5054(6) 0.6991(11) 0.057(3) Uani 1 1 d .
H10 H 0.2181 0.4939 0.7617 0.068 Uiso 1 1 calc R
C11 C 0.0416(13) 0.5765(7) 0.6123(14) 0.082(5) Uani 1 1 d .
H11A H 0.0136 0.5625 0.6725 0.099 Uiso 1 1 calc R
H11B H -0.0349 0.5686 0.5374 0.099 Uiso 1 1 calc R
C12 C 0.0685(13) 0.6432(7) 0.6260(11) 0.071(4) Uani 1 1 d .
H12A H 0.0998 0.6567 0.5673 0.085 Uiso 1 1 calc R
H12B H -0.0190 0.6635 0.6121 0.085 Uiso 1 1 calc R
C13 C 0.1754(13) 0.6604(6) 0.7433(10) 0.062(4) Uani 1 1 d .
H13A H 0.2602 0.6375 0.7591 0.075 Uiso 1 1 calc R
H13B H 0.1405 0.6492 0.8010 0.075 Uiso 1 1 calc R
C14 C 0.2131(16) 0.7254(7) 0.7583(12) 0.075(4) Uani 1 1 d .
H14A H 0.1277 0.7490 0.7317 0.090 Uiso 1 1 calc R
H14B H 0.2664 0.7338 0.8403 0.090 Uiso 1 1 calc R
C15 C 0.2747(13) 0.7936(6) 0.6276(10) 0.058(3) Uani 1 1 d .
H15 H 0.2037 0.8214 0.6144 0.070 Uiso 1 1 calc R
C16 C 0.3738(12) 0.7961(6) 0.5857(10) 0.059(3) Uani 1 1 d .
H16 H 0.3828 0.8258 0.5377 0.070 Uiso 1 1 calc R
C17 C 0.4112(16) 0.7177(7) 0.6928(11) 0.073(4) Uani 1 1 d .
H17 H 0.4530 0.6834 0.7340 0.088 Uiso 1 1 calc R
C18 C 0.5792(11) 0.7353(7) 0.6020(11) 0.067(4) Uani 1 1 d .
H18A H 0.6504 0.7179 0.6716 0.080 Uiso 1 1 calc R
H18B H 0.6164 0.7726 0.5875 0.080 Uiso 1 1 calc R
N1 N 0.3443(10) 0.4847(5) 0.6786(7) 0.050(3) Uani 1 1 d .
N2 N 0.1651(9) 0.5440(5) 0.6202(8) 0.053(3) Uani 1 1 d .
N3 N 0.2966(11) 0.7434(5) 0.6927(8) 0.056(3) Uani 1 1 d .
N4 N 0.4571(9) 0.7485(5) 0.6249(8) 0.059(3) Uani 1 1 d .
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_3
I1 Bi1 I2 87.76(3) .
I1 Bi1 I3 172.21(2) 3_565
I1 Bi1 I3 88.96(2) .
I1 Bi1 I4 101.12(3) .
I1 Bi1 I5 92.15(3) .
I2 Bi1 I3 91.65(2) .
I2 Bi1 I3 88.82(3) 3_565
I2 Bi1 I4 87.13(2) .
I2 Bi1 I5 175.70(3) .
I3 Bi1 I3 84.14(2) 3_565
I4 Bi1 I3 85.69(2) 3_565
I4 Bi1 I3 169.78(3) .
I4 Bi1 I5 88.67(2) .
I5 Bi1 I3 92.65(2) .
I5 Bi1 I3 91.78(2) 3_565
Bi1 I3 Bi1 95.86(2) 3_565
C6 C1 C2 121.3(12) .
C3 C2 C1 121.5(11) .
C2 C3 C4 117.6(12) .
C2 C3 C18 125.1(10) 3_666
C4 C3 C18 117.2(11) 3_666
C3 C4 C5 121.3(13) .
C4 C5 C6 121.2(12) .
C1 C6 C5 116.8(12) .
C1 C6 C7 123.4(12) .
C5 C6 C7 119.7(12) .
C6 C7 N1 110.8(9) .
C9 C8 N1 106.5(11) .
C8 C9 N2 108.0(11) .
N2 C10 N1 111.0(10) .
N2 C11 C12 111.7(11) .
C13 C12 C11 113.2(12) .
C12 C13 C14 115.2(12) .
N3 C14 C13 112.2(11) .
C16 C15 N3 107.8(12) .
N4 C16 C15 108.2(11) .
N3 C17 N4 109.7(12) .
N4 C18 C3 115.9(10) 3_666
C8 N1 C7 123.6(10) .
C10 N1 C7 129.1(10) .
C10 N1 C8 107.2(10) .
C9 N2 C11 125.1(12) .
C10 N2 C9 107.2(10) .
C10 N2 C11 127.7(11) .
C15 N3 C14 124.8(12) .
C17 N3 C14 128.2(11) .
C17 N3 C15 106.7(11) .
C16 N4 C18 125.7(12) .
C17 N4 C16 107.4(11) .
C17 N4 C18 126.9(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 I1 2.9701(10) .
Bi1 I2 2.9937(8) .
Bi1 I3 3.2342(9) 3_565
Bi1 I3 3.1719(7) .
Bi1 I4 3.0269(8) .
Bi1 I5 3.1631(9) .
I3 Bi1 3.2342(9) 3_565
C1 C2 1.384(16) .
C1 C6 1.379(15) .
C2 C3 1.367(15) .
C3 C4 1.377(14) .
C3 C18 1.504(16) 3_666
C4 C5 1.378(19) .
C5 C6 1.389(18) .
C6 C7 1.468(17) .
C7 N1 1.488(15) .
C8 C9 1.345(16) .
C8 N1 1.377(13) .
C9 N2 1.372(13) .
C10 N1 1.322(14) .
C10 N2 1.301(15) .
C11 C12 1.519(19) .
C11 N2 1.449(15) .
C12 C13 1.491(16) .
C13 C14 1.501(18) .
C14 N3 1.481(15) .
C15 C16 1.342(15) .
C15 N3 1.355(14) .
C16 N4 1.336(15) .
C17 N3 1.328(16) .
C17 N4 1.332(15) .
C18 C3 1.504(16) 3_666
C18 N4 1.448(14) .
