#------------------------------------------------------------------------------
#$Date: 2019-12-20 11:55:56 +0200 (Fri, 20 Dec 2019) $
#$Revision: 245429 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/66/1556690.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_1556690
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            'C14 H23 I14 N4 O'
_chemical_formula_weight         2039.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 104.671(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.226(1)
_cell_length_b                   13.060(1)
_cell_length_c                   17.377(2)
_cell_measurement_reflns_used    7359
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.36
_cell_measurement_theta_min      2.28
_cell_volume                     2025.5(4)
_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 0.954
_diffrn_measured_fraction_theta_max 0.928
_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  0.0469
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3116
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         2.282
_exptl_absorpt_coefficient_mu    10.714
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.3374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ' SADABS-2016/2'
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    3.345
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1770
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         2.637
_refine_diff_density_min         -3.065
_refine_diff_density_rms         0.525
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0779
_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)+(0.1443P)²+31.8804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2092
_refine_ls_wR_factor_ref         0.2353
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2244
_reflns_number_total             2810
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Inorganics-2019-7-48.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               1556690
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
I2 I 0.3344(2) 0.7500 0.79918(12) 0.0152(5) Uani 1 2 d S T P . .
I3 I 0.0341(2) 0.7500 0.85098(12) 0.0166(5) Uani 1 2 d S T P . .
C4 C 0.601(3) 0.4342(17) 0.7227(15) 0.019(5) Uani 1 1 d . U . . .
H4A H 0.6307 0.4930 0.7593 0.023 Uiso 1 1 calc R U . . .
H4B H 0.6318 0.4493 0.6732 0.023 Uiso 1 1 calc R U . . .
I7 I 0.4908(2) 0.2500 0.49502(12) 0.0177(5) Uani 1 2 d S T P . .
N1 N 0.620(3) 0.2500 0.7292(17) 0.020(6) Uani 1 2 d S TU P . .
I1 I 0.6007(2) 0.7500 0.75191(13) 0.0195(5) Uani 1 2 d S T P . .
I9 I 0.87626(17) 0.42957(11) 0.57802(9) 0.0186(4) Uani 1 1 d . . . . .
I6 I 0.2196(2) 0.2500 0.54128(13) 0.0225(6) Uani 1 2 d S T P . .
I10 I 0.9479(18) 0.575(2) 0.6965(14) 0.017(3) Uani 0.57(15) 1 d . U P . .
C7 C 0.387(3) 0.3445(19) 0.8266(16) 0.026(5) Uani 1 1 d . U . . .
H7A H 0.3298 0.3551 0.8671 0.031 Uiso 1 1 calc R U . . .
H7B H 0.4940 0.3360 0.8544 0.031 Uiso 1 1 calc R U . . .
I4 I 0.18446(19) 0.56055(12) 0.95769(9) 0.0238(5) Uani 1 1 d . . . . .
I5 I -0.2989(11) 0.9029(3) 0.9412(2) 0.0272(14) Uani 0.78(3) 1 d . U P . .
O1 O 0.991(3) 0.2500 0.9224(16) 0.032(6) Uani 1 2 d S TU P . .
H1 H 1.0141 0.1894 0.9363 0.047 Uiso 0.5 1 calc R U P . .
C5 C 0.363(4) 0.493(2) 0.6395(19) 0.041(7) Uani 1 1 d . U . . .
H5A H 0.2543 0.4841 0.6270 0.061 Uiso 1 1 calc R U . . .
H5B H 0.3882 0.5637 0.6577 0.061 Uiso 1 1 calc R U . . .
H5C H 0.3987 0.4804 0.5918 0.061 Uiso 1 1 calc R U . . .
N3 N 0.331(3) 0.2500 0.7786(16) 0.014(5) Uani 1 2 d S TU P . .
C3 C 0.681(3) 0.3366(18) 0.7616(13) 0.018(5) Uani 1 1 d . U . . .
C6 C 0.369(4) 0.433(2) 0.7738(18) 0.035(7) Uani 1 1 d . U . . .
H6A H 0.4142 0.4932 0.8050 0.042 Uiso 1 1 calc R U . . .
H6B H 0.2602 0.4466 0.7530 0.042 Uiso 1 1 calc R U . . .
C1 C 0.869(4) 0.2500 0.8597(19) 0.016(6) Uani 1 2 d S TU P . .
I8 I 0.7874(2) 0.2500 0.44642(12) 0.0148(5) Uani 1 2 d S T P . .
I5' I -0.346(4) 0.9127(13) 0.9447(10) 0.035(4) Uani 0.22(3) 1 d . U P . .
I10' I 0.941(3) 0.587(2) 0.687(2) 0.021(3) Uani 0.43(15) 1 d . U P . .
C2 C 0.806(3) 0.3450(19) 0.8285(15) 0.023(5) Uani 1 1 d . U . . .
H2 H 0.8440 0.4090 0.8507 0.028 Uiso 1 1 calc R U . . .
N2 N 0.438(2) 0.4192(14) 0.7045(11) 0.014(4) Uani 1 1 d . U . . .
H2A H 0.4152 0.3481 0.6835 0.017 Uiso 1 1 calc R U . . .
C8 C 0.170(4) 0.2500 0.763(2) 0.030(8) Uani 1 2 d S TU P . .
H8A H 0.1294 0.1892 0.7313 0.045 Uiso 0.5 1 calc R U P . .
H8B H 0.1400 0.2490 0.8129 0.045 Uiso 1 2 calc R U P . .
H8C H 0.1296 0.3118 0.7326 0.045 Uiso 0.5 1 calc R U P . .
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'
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'
O O 0.0106 0.0060 '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 I2 I3 179.59(9) . .
I2 I3 I4 83.15(6) . .
I2 I3 I10 79.8(3) . 1_455
I4 I3 I10 85.4(5) . 1_455
I2 I3 I10' 79.5(4) . 1_455
I4 I3 I10' 89.1(7) . 1_455
I10 I3 I10' 3.8(5) 1_455 1_455
N2 C4 C3 109.5(19) . .
I6 I7 I8 179.44(9) . .
C3 N1 C3 117(3) . 4_565
I10 I9 I10' 4.8(6) . .
I10 I9 I8 176.7(6) . .
I10' I9 I8 177.4(8) . .
C6 C7 N3 109(2) . .
I5' I4 I5 9.8(6) 2_547 2_547
I5' I4 I3 172.7(7) 2_547 .
I5 I4 I3 174.83(19) 2_547 .
I5' I5 I4 85.9(19) . 2_557
C8 N3 C7 107.4(19) . .
C8 N3 C7 107.4(19) . 4_565
C7 N3 C7 110(2) . 4_565
N1 C3 C2 126(2) . .
N1 C3 C4 114.5(18) . .
C2 C3 C4 120(2) . .
C7 C6 N2 114(2) . .
O1 C1 C2 119.0(13) . 4_565
O1 C1 C2 119.0(13) . .
C2 C1 C2 122(3) 4_565 .
I7 I8 I9 83.64(6) . .
I5 I5' I4 84(2) . 2_557
C1 C2 C3 115(2) . .
C4 N2 C5 109(2) . .
C4 N2 C6 115.5(19) . .
C5 N2 C6 108(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I2 I1 2.780(3) .
I2 I3 3.122(3) .
I3 I4 3.1908(19) .
I3 I10 3.460(12) 1_455
I3 I10' 3.48(2) 1_455
C4 N2 1.48(3) .
C4 C3 1.54(3) .
I7 I6 2.815(3) .
I7 I8 3.061(3) .
N1 C3 1.32(3) .
N1 C3 1.33(3) 4_565
I9 I10 2.757(12) .
I9 I10' 2.759(18) .
I9 I8 3.233(2) .
C7 C6 1.46(4) .
C7 N3 1.51(3) .
I4 I5' 2.746(14) 2_547
I4 I5 2.739(3) 2_547
I5 I5' 0.47(3) .
I5 I4 2.739(3) 2_557
O1 C1 1.35(4) .
C5 N2 1.51(3) .
N3 C8 1.44(5) .
N3 C7 1.51(3) 4_565
C3 C2 1.42(3) .
C6 N2 1.51(4) .
C1 C2 1.42(3) 4_565
C1 C2 1.42(3) .
I5' I4 2.746(14) 2_557
