#------------------------------------------------------------------------------
#$Date: 2019-10-28 17:40:17 +0200 (Mon, 28 Oct 2019) $
#$Revision: 220149 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/50/4515004.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_4515004
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     heavy
_audit_creation_date             2017-04-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                118.515(5)
_cell_angle_beta                 101.244(4)
_cell_angle_gamma                106.977(4)
_cell_formula_units_Z            1
_cell_length_a                   11.8609(5)
_cell_length_b                   12.0302(6)
_cell_length_c                   12.3115(5)
_cell_measurement_reflns_used    4489
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1830
_cell_measurement_theta_min      3.8540
_cell_volume                     1354.45(16)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   24.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -99.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   24.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1755  -99.0000 -120.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega  -47.00   81.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661    0.0000 -150.0000 128

#__ type_ start__ end____ width___ exp.time_
  4 omega  -24.00   54.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -99.0000   60.0000 78

#__ type_ start__ end____ width___ exp.time_
  5 omega   10.00   36.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661  -37.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega    6.00   87.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0661   37.0000 -120.0000 81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0674564000
_diffrn_orient_matrix_UB_12      -0.0427218000
_diffrn_orient_matrix_UB_13      -0.0320371000
_diffrn_orient_matrix_UB_21      0.0094757000
_diffrn_orient_matrix_UB_22      -0.0609340000
_diffrn_orient_matrix_UB_23      -0.0357644000
_diffrn_orient_matrix_UB_31      0.0021878000
_diffrn_orient_matrix_UB_32      -0.0093463000
_diffrn_orient_matrix_UB_33      0.0529348000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0480
_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       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11217
_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         26.372
_diffrn_reflns_theta_min         3.379
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    12.219
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66869
_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    2.790
_exptl_crystal_description       prism
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.945
_refine_diff_density_min         -2.483
_refine_diff_density_rms         0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0364P)²+7.7884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4394
_reflns_number_total             5532
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao9b00669_si_002.cif
_cod_data_source_block           4
_cod_original_cell_volume        1354.44(12)
_cod_database_code               4515004
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C38H70N2O12Bi1
_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 99.82
_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:
 C2(H2), C3(H3), 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, -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
Bi1 Bi 0.48933(3) 0.35215(4) 0.28245(3) 0.03302(11) Uani 1 1 d .
I1 I 0.24302(7) 0.13237(8) 0.23074(8) 0.0552(2) Uani 1 1 d .
I2 I 0.61834(7) 0.41534(8) 0.57625(7) 0.04569(18) Uani 1 1 d .
I3 I 0.58248(11) 0.14647(11) 0.18681(12) 0.0853(3) Uani 1 1 d .
I4 I 0.73794(6) 0.58220(8) 0.32104(7) 0.04714(18) Uani 1 1 d .
I5 I 0.37615(8) 0.29129(10) 0.00971(8) 0.0659(2) Uani 1 1 d .
C1 C 0.8673(9) 0.2851(10) 0.9645(9) 0.036(2) Uani 1 1 d .
C2 C 0.9769(9) 0.2676(11) 0.9573(10) 0.044(2) Uani 1 1 d .
H2 H 1.0134 0.2397 1.0077 0.053 Uiso 1 1 calc R
C3 C 1.0324(10) 0.2904(11) 0.8778(12) 0.051(3) Uani 1 1 d .
H3 H 1.1056 0.2778 0.8743 0.062 Uiso 1 1 calc R
C4 C 0.9799(10) 0.3318(11) 0.8038(11) 0.051(3) Uani 1 1 d .
H4 H 1.0171 0.3465 0.7490 0.061 Uiso 1 1 calc R
C5 C 0.8726(10) 0.3519(11) 0.8097(11) 0.047(3) Uani 1 1 d .
H5 H 0.8378 0.3808 0.7594 0.056 Uiso 1 1 calc R
C6 C 0.8159(9) 0.3293(10) 0.8900(10) 0.039(2) Uani 1 1 d .
C7 C 0.6924(9) 0.3474(11) 0.8870(10) 0.042(2) Uani 1 1 d .
H7A H 0.6825 0.3685 0.9701 0.051 Uiso 1 1 calc R
H7B H 0.6995 0.4266 0.8812 0.051 Uiso 1 1 calc R
C8 C 0.5636(10) 0.0839(11) 0.7127(11) 0.045(2) Uani 1 1 d .
H8 H 0.6234 0.0555 0.7370 0.054 Uiso 1 1 calc R
C9 C 0.4475(10) -0.0004(11) 0.6134(11) 0.047(2) Uani 1 1 d .
H9 H 0.4112 -0.0984 0.5554 0.056 Uiso 1 1 calc R
C10 C 0.4741(9) 0.2176(12) 0.7106(11) 0.041(2) Uani 1 1 d .
H10 H 0.4602 0.2964 0.7320 0.050 Uiso 1 1 calc R
C11 C 0.2634(10) 0.0361(14) 0.5191(11) 0.055(3) Uani 1 1 d .
H11A H 0.2392 -0.0542 0.4369 0.065 Uiso 1 1 calc R
H11B H 0.2652 0.1030 0.4959 0.065 Uiso 1 1 calc R
C12 C 0.1635(10) 0.0198(14) 0.5782(12) 0.059(3) Uani 1 1 d .
H12A H 0.1844 0.1121 0.6557 0.071 Uiso 1 1 calc R
H12B H 0.0804 -0.0140 0.5118 0.071 Uiso 1 1 calc R
C13 C 0.1536(10) -0.0773(12) 0.6200(12) 0.052(3) Uani 1 1 d .
H13A H 0.2375 -0.0469 0.6828 0.062 Uiso 1 1 calc R
H13B H 0.1272 -0.1713 0.5417 0.062 Uiso 1 1 calc R
C14 C 0.0565(10) -0.0839(12) 0.6874(12) 0.051(3) Uani 1 1 d .
H14A H 0.0803 0.0102 0.7640 0.061 Uiso 1 1 calc R
H14B H -0.0289 -0.1195 0.6236 0.061 Uiso 1 1 calc R
C15 C -0.0179(10) -0.3175(13) 0.6603(12) 0.060(3) Uani 1 1 d .
H15 H -0.0852 -0.3726 0.5759 0.072 Uiso 1 1 calc R
C16 C 0.0224(12) -0.3638(13) 0.7327(12) 0.070(4) Uani 1 1 d .
H16 H -0.0100 -0.4568 0.7072 0.084 Uiso 1 1 calc R
C17 C 0.1396(9) -0.1374(11) 0.8480(10) 0.041(2) Uani 1 1 d .
H17 H 0.2018 -0.0456 0.9161 0.049 Uiso 1 1 calc R
C18 C 0.2001(10) -0.2516(14) 0.9549(11) 0.053(3) Uani 1 1 d .
H18A H 0.2752 -0.1606 1.0164 0.064 Uiso 1 1 calc R
H18B H 0.2299 -0.3221 0.9122 0.064 Uiso 1 1 calc R
N1 N 0.5796(7) 0.2205(8) 0.7731(8) 0.0345(17) Uani 1 1 d .
N2 N 0.3907(8) 0.0848(10) 0.6123(9) 0.043(2) Uani 1 1 d .
N3 N 0.0564(7) -0.1763(9) 0.7316(8) 0.0414(19) Uani 1 1 d .
N4 N 0.1204(8) -0.2478(9) 0.8515(8) 0.044(2) 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 89.45(2) .
I1 Bi1 I2 87.07(2) 2_666
I1 Bi1 I4 176.36(2) .
I2 Bi1 I2 87.750(18) 2_666
I3 Bi1 I1 89.77(3) .
I3 Bi1 I2 85.75(3) .
I3 Bi1 I2 172.80(2) 2_666
I3 Bi1 I4 91.41(3) .
I3 Bi1 I5 92.80(3) .
I4 Bi1 I2 94.07(2) .
I4 Bi1 I2 92.15(2) 2_666
I5 Bi1 I1 91.31(3) .
I5 Bi1 I2 178.36(2) .
I5 Bi1 I2 93.74(2) 2_666
I5 Bi1 I4 85.19(2) .
Bi1 I2 Bi1 92.250(18) 2_666
C2 C1 C6 118.1(8) .
C2 C1 C18 122.3(8) 2_657
C6 C1 C18 119.5(8) 2_657
C3 C2 C1 121.6(9) .
C4 C3 C2 119.7(10) .
C3 C4 C5 120.3(9) .
C4 C5 C6 120.4(10) .
C1 C6 C7 122.5(8) .
C5 C6 C1 119.8(9) .
C5 C6 C7 117.6(9) .
N1 C7 C6 111.5(8) .
C9 C8 N1 107.7(9) .
C8 C9 N2 107.3(9) .
N1 C10 N2 109.4(8) .
N2 C11 C12 112.0(8) .
C13 C12 C11 114.4(9) .
C12 C13 C14 112.7(9) .
N3 C14 C13 109.5(8) .
C16 C15 N3 107.9(10) .
C15 C16 N4 106.9(11) .
N4 C17 N3 109.5(9) .
N4 C18 C1 114.3(8) 2_657
C8 N1 C7 126.5(8) .
C10 N1 C7 125.3(8) .
C10 N1 C8 108.1(9) .
C9 N2 C11 125.7(10) .
C10 N2 C9 107.5(8) .
C10 N2 C11 126.9(9) .
C15 N3 C14 127.4(9) .
C17 N3 C14 125.0(9) .
C17 N3 C15 107.4(8) .
C16 N4 C18 125.2(10) .
C17 N4 C16 108.2(9) .
C17 N4 C18 126.1(10) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 I1 3.0146(8) .
Bi1 I2 3.2466(7) .
Bi1 I2 3.2846(8) 2_666
Bi1 I3 2.8375(9) .
Bi1 I4 3.1643(8) .
Bi1 I5 2.9889(8) .
I2 Bi1 3.2845(7) 2_666
C1 C2 1.389(12) .
C1 C6 1.391(12) .
C1 C18 1.512(13) 2_657
C2 C3 1.366(13) .
C3 C4 1.363(15) .
C4 C5 1.372(14) .
C5 C6 1.384(13) .
C6 C7 1.538(13) .
C7 N1 1.456(12) .
C8 C9 1.328(14) .
C8 N1 1.373(12) .
C9 N2 1.386(12) .
C10 N1 1.316(11) .
C10 N2 1.326(13) .
C11 C12 1.519(14) .
C11 N2 1.450(12) .
C12 C13 1.470(14) .
C13 C14 1.550(14) .
C14 N3 1.453(11) .
C15 C16 1.340(15) .
C15 N3 1.353(14) .
C16 N4 1.371(14) .
C17 N3 1.336(12) .
C17 N4 1.303(12) .
C18 C1 1.512(13) 2_657
C18 N4 1.460(12) .
