#------------------------------------------------------------------------------
#$Date: 2019-12-20 11:55:56 +0200 (Fri, 20 Dec 2019) $
#$Revision: 245429 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/66/1556689.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_1556689
loop_
_publ_author_name
'Savastano, M.'
'Martinez-Camarena, A.'
'Bazzicalupi, C.'
'Delgado-Pinar, E.'
'Llinares, J.M.'
'Mariani, P.'
'Verdejo, B.'
'Garcia-Espana, E.'
'Bianchi, A.'
_publ_section_title
;
 Stabilization of Supramolecular Networks of Polyiodides with Protonated
 Small Tetra-azacyclophanes
;
_journal_name_full               Inorganics
_journal_page_first              48
_journal_paper_doi               10.3390/inorganics7040048
_journal_volume                  7
_journal_year                    2019
_chemical_formula_sum            'C22 H40 I16 N8'
_chemical_formula_weight         2447.02
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                108.167(4)
_cell_angle_beta                 94.071(5)
_cell_angle_gamma                104.453(4)
_cell_formula_units_Z            2
_cell_length_a                   8.300(1)
_cell_length_b                   16.191(2)
_cell_length_c                   21.221(3)
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.33
_cell_measurement_theta_min      2.54
_cell_volume                     2589.3(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Mercury 3.10.1'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            59174
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.543
_exptl_absorpt_coefficient_mu    9.586
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.3769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    3.138
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2152
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.060
_refine_diff_density_max         3.422
_refine_diff_density_min         -4.595
_refine_diff_density_rms         0.295
_refine_ls_extinction_coef       .
_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     415
_refine_ls_number_reflns         9410
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0619P)²+27.2314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8865
_reflns_number_total             9410
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Inorganics-2019-7-48.cif
_cod_data_source_block           1
_cod_original_cell_volume        2589.5(6)
_cod_database_code               1556689
_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   0.161
_shelx_estimated_absorpt_t_max   0.597
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
I1 I 0.23093(6) 0.46590(3) 0.23440(2) 0.01921(11) Uani 1 1 d . . . . .
I2 I -0.19956(6) 0.58618(3) 0.26881(2) 0.02235(12) Uani 1 1 d . . . . .
I3 I 0.14602(6) 0.29541(3) 0.25877(2) 0.02393(12) Uani 1 1 d . . . . .
I4 I 0.32517(6) 0.63708(3) 0.20812(3) 0.02446(12) Uani 1 1 d . . . . .
I5 I -0.29388(7) 0.40299(3) 0.29154(3) 0.02758(13) Uani 1 1 d . . . . .
I6 I -0.11922(6) 0.75787(3) 0.25352(2) 0.02640(12) Uani 1 1 d . . . . .
I7 I 0.16715(7) 1.04027(3) 0.21588(2) 0.02598(13) Uani 1 1 d . . . . .
I8 I 0.45974(7) 0.91650(3) 0.30836(2) 0.02583(12) Uani 1 1 d . . . . .
I9 I 0.69423(6) 1.01734(3) 0.44283(2) 0.02417(12) Uani 1 1 d . . . . .
I10 I -0.23434(7) 0.04446(3) -0.01349(3) 0.02684(13) Uani 1 1 d . . . . .
I11 I 0.50668(7) 1.09365(3) 0.16486(3) 0.02808(13) Uani 1 1 d . . . . .
I12 I -0.04687(6) 0.16487(3) 0.10844(3) 0.02603(13) Uani 1 1 d . . . . .
I14 I -0.13541(7) 0.99780(4) 0.26404(3) 0.03248(14) Uani 1 1 d . . . . .
I15 I 0.90053(7) 1.10583(5) 0.56956(3) 0.04407(18) Uani 1 1 d . . . . .
I13 I 0.53651(8) 0.45871(3) -0.06400(3) 0.03620(15) Uani 1 1 d . . . . .
I16 I -0.45227(11) 0.47218(4) 0.43610(4) 0.0681(3) Uani 1 1 d . U . . .
N1 N 0.6946(10) 1.2584(4) 0.4841(3) 0.0318(16) Uani 1 1 d . . . . .
C1 C 0.7425(13) 1.2585(6) 0.4253(4) 0.035(2) Uani 1 1 d . . . . .
C2 C 0.8875(12) 1.3174(7) 0.4208(5) 0.038(2) Uani 1 1 d . . . . .
H2 H 0.9182 1.3159 0.3783 0.045 Uiso 1 1 calc R U . . .
C3 C 0.9877(11) 1.3787(7) 0.4789(5) 0.038(2) Uani 1 1 d . . . . .
H3 H 1.0896 1.4197 0.4766 0.046 Uiso 1 1 calc R U . . .
C4 C 0.9419(10) 1.3814(6) 0.5407(5) 0.0310(18) Uani 1 1 d . . . . .
H4 H 1.0088 1.4243 0.5814 0.037 Uiso 1 1 calc R U . . .
C5 C 0.7934(10) 1.3183(5) 0.5403(4) 0.0239(16) Uani 1 1 d . . . . .
C6 C 0.7335(12) 1.3177(6) 0.6058(4) 0.038(2) Uani 1 1 d . . . . .
H6C H 0.8273 1.3177 0.6373 0.046 Uiso 1 1 calc R U . . .
H6D H 0.7000 1.3735 0.6262 0.046 Uiso 1 1 calc R U . . .
N2 N 0.4595(12) 1.1490(5) 0.3803(4) 0.048(2) Uani 1 1 d . . . . .
H2A H 0.4803 1.1357 0.4181 0.058 Uiso 1 1 calc R U . . .
H2B H 0.4078 1.0956 0.3466 0.058 Uiso 1 1 calc R U . . .
C7 C 0.4223(10) 1.2549(6) 0.6090(5) 0.0324(19) Uani 1 1 d . . . . .
H7C H 0.4428 1.3130 0.6465 0.039 Uiso 1 1 calc R U . . .
H7D H 0.3516 1.2060 0.6222 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3303(13) 1.2601(6) 0.5465(5) 0.046(3) Uani 1 1 d . . . . .
H8C H 0.2249 1.2759 0.5563 0.056 Uiso 1 1 calc R U . . .
H8D H 0.4019 1.3079 0.5324 0.056 Uiso 1 1 calc R U . . .
N3 N 0.2914(10) 1.1730(5) 0.4928(4) 0.040(2) Uani 1 1 d . . . . .
H3A H 0.2214 1.1304 0.5058 0.050 Uiso 1 1 d . U . . .
C9 C 0.2109(14) 1.1717(8) 0.4294(6) 0.052(3) Uani 1 1 d . U . . .
H9A H 0.1332 1.2101 0.4381 0.062 Uiso 1 1 calc R U . . .
H9B H 0.1438 1.1090 0.4025 0.062 Uiso 1 1 calc R U . . .
C10 C 0.3361(15) 1.2052(8) 0.3921(6) 0.053(3) Uani 1 1 d . U . . .
H10A H 0.3976 1.2695 0.4175 0.064 Uiso 1 1 calc R U . . .
H10B H 0.2794 1.2020 0.3483 0.064 Uiso 1 1 calc R U . . .
N4 N 0.5868(7) 1.2363(4) 0.5957(3) 0.0192(12) Uani 1 1 d . . . . .
H4A H 0.5723 1.1983 0.5526 0.023 Uiso 1 1 calc R U . . .
H4B H 0.6135 1.2065 0.6230 0.023 Uiso 1 1 calc R U . . .
C11 C 0.6236(19) 1.1889(6) 0.3629(4) 0.061(4) Uani 1 1 d . . . . .
H11A H 0.6057 1.2184 0.3297 0.073 Uiso 1 1 calc R U . . .
H11B H 0.6754 1.1401 0.3422 0.073 Uiso 1 1 calc R U . . .
N5 N -0.2727(8) 0.2745(4) -0.0054(3) 0.0220(13) Uani 1 1 d . . . . .
C12 C -0.2210(11) 0.2582(6) -0.0656(4) 0.0274(17) Uani 1 1 d . . . . .
C13 C -0.0760(12) 0.3122(7) -0.0760(4) 0.035(2) Uani 1 1 d . . . . .
H13 H -0.0431 0.2989 -0.1192 0.042 Uiso 1 1 calc R U . . .
C14 C 0.0206(11) 0.3857(7) -0.0227(4) 0.035(2) Uani 1 1 d . . . . .
H14 H 0.1216 0.4237 -0.0287 0.042 Uiso 1 1 calc R U . . .
C15 C -0.0298(10) 0.4037(6) 0.0388(4) 0.0267(17) Uani 1 1 d . . . . .
H15 H 0.0343 0.4543 0.0763 0.032 Uiso 1 1 calc R U . . .
C16 C -0.1761(9) 0.3462(5) 0.0449(4) 0.0181(14) Uani 1 1 d . . . . .
C17 C -0.2442(9) 0.3656(5) 0.1115(4) 0.0245(16) Uani 1 1 d . . . . .
H17A H -0.1513 0.3803 0.1488 0.029 Uiso 1 1 calc R U . . .
H17B H -0.2878 0.4189 0.1192 0.029 Uiso 1 1 calc R U . . .
N6 N -0.3825(8) 0.2859(4) 0.1117(3) 0.0211(13) Uani 1 1 d . . . . .
H6A H -0.3528 0.2697 0.1473 0.025 Uiso 1 1 calc R U . . .
H6B H -0.3901 0.2385 0.0737 0.025 Uiso 1 1 calc R U . . .
C18 C -0.5542(10) 0.3005(6) 0.1157(5) 0.0289(18) Uani 1 1 d . . . . .
H18A H -0.5421 0.3636 0.1447 0.035 Uiso 1 1 calc R U . . .
H18B H -0.6211 0.2591 0.1364 0.035 Uiso 1 1 calc R U . . .
C19 C -0.6459(10) 0.2832(6) 0.0467(5) 0.0316(19) Uani 1 1 d . . . . .
H19A H -0.7551 0.2970 0.0506 0.038 Uiso 1 1 calc R U . . .
H19B H -0.5779 0.3232 0.0254 0.038 Uiso 1 1 calc R U . . .
N7 N -0.6750(9) 0.1883(4) 0.0051(4) 0.0330(17) Uani 1 1 d . . . . .
H7A H -0.7441 0.1524 0.0237 0.050 Uiso 1 1 d . U . . .
C20 C -0.7528(13) 0.1670(6) -0.0646(6) 0.047(3) Uani 1 1 d . . . . .
H20A H -0.8356 0.2014 -0.0654 0.057 Uiso 1 1 calc R U . . .
H20B H -0.8131 0.1015 -0.0844 0.057 Uiso 1 1 calc R U . . .
C21 C -0.6196(14) 0.1914(6) -0.1050(5) 0.048(3) Uani 1 1 d . . . . .
H21A H -0.6715 0.1762 -0.1522 0.057 Uiso 1 1 calc R U . . .
H21B H -0.5622 0.2574 -0.0865 0.057 Uiso 1 1 calc R U . . .
N8 N -0.4956(11) 0.1398(5) -0.1023(4) 0.0378(19) Uani 1 1 d . . . . .
H8A H -0.5420 0.0815 -0.1303 0.045 Uiso 1 1 calc R U . . .
H8B H -0.4774 0.1386 -0.0599 0.045 Uiso 1 1 calc R U . . .
C22 C -0.3297(15) 0.1762(6) -0.1211(4) 0.043(2) Uani 1 1 d . . . . .
H22A H -0.3485 0.1922 -0.1618 0.052 Uiso 1 1 calc R U . . .
H22B H -0.2708 0.1285 -0.1319 0.052 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'
I I -0.4742 1.8119 '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
I3 I1 I4 178.36(2) . .
I6 I2 I5 177.27(2) . .
I1 I3 I12 98.14(2) . .
I14 I7 I11 178.29(2) . .
I15 I9 I8 177.44(3) . .
I10 I12 I3 174.25(2) . .
C5 N1 C1 118.1(8) . .
N1 C1 C2 122.6(9) . .
N1 C1 C11 115.6(9) . .
C2 C1 C11 121.8(8) . .
C1 C2 C3 118.7(8) . .
C2 C3 C4 120.5(8) . .
C3 C4 C5 116.7(8) . .
N1 C5 C4 123.4(8) . .
N1 C5 C6 116.7(7) . .
C4 C5 C6 119.9(7) . .
N4 C6 C5 111.7(6) . .
C11 N2 C10 117.7(8) . .
N4 C7 C8 110.1(8) . .
N3 C8 C7 109.3(7) . .
C9 N3 C8 113.9(8) . .
N3 C9 C10 110.6(9) . .
C9 C10 N2 110.2(9) . .
C7 N4 C6 116.1(7) . .
N2 C11 C1 110.8(8) . .
C16 N5 C12 116.8(7) . .
N5 C12 C13 122.6(8) . .
N5 C12 C22 115.9(8) . .
C13 C12 C22 121.5(8) . .
C12 C13 C14 118.9(8) . .
C15 C14 C13 119.5(8) . .
C14 C15 C16 117.9(8) . .
N5 C16 C15 124.3(7) . .
N5 C16 C17 115.1(6) . .
C15 C16 C17 120.4(7) . .
N6 C17 C16 111.6(6) . .
C17 N6 C18 115.8(6) . .
N6 C18 C19 110.9(7) . .
N7 C19 C18 109.8(7) . .
C19 N7 C20 113.4(7) . .
N7 C20 C21 109.8(7) . .
N8 C21 C20 108.7(8) . .
C21 N8 C22 115.4(7) . .
N8 C22 C12 111.7(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 I3 2.8905(7) .
I1 I4 2.9238(7) .
I2 I6 2.8188(8) .
I2 I5 3.0707(8) .
I3 I12 3.2541(8) .
I7 I14 2.7866(9) .
I7 I11 3.1083(8) .
I8 I9 3.0523(8) .
I9 I15 2.8172(8) .
I10 I12 2.7723(8) .
I13 I13 2.8118(13) 2_665
I16 I16 2.816(2) 2_466
N1 C5 1.333(11) .
N1 C1 1.337(11) .
C1 C2 1.366(14) .
C1 C11 1.525(14) .
C2 C3 1.369(15) .
C3 C4 1.382(13) .
C4 C5 1.388(11) .
C5 C6 1.511(12) .
C6 N4 1.500(10) .
N2 C11 1.480(16) .
N2 C10 1.516(14) .
C7 N4 1.497(10) .
C7 C8 1.519(13) .
C8 N3 1.452(11) .
N3 C9 1.451(14) .
C9 C10 1.452(17) .
N5 C16 1.330(10) .
N5 C12 1.346(10) .
C12 C13 1.376(13) .
C12 C22 1.497(13) .
C13 C14 1.376(14) .
C14 C15 1.367(12) .
C15 C16 1.374(11) .
C16 C17 1.531(10) .
C17 N6 1.499(10) .
N6 C18 1.506(9) .
C18 C19 1.511(12) .
C19 N7 1.462(11) .
N7 C20 1.468(13) .
C20 C21 1.497(17) .
C21 N8 1.487(12) .
N8 C22 1.490(14) .
