#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:39:59 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180514 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/83/7218353.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_7218353
loop_
_publ_author_name
'Peuronen, Anssi'
'Rinta, Heikki'
'Lahtinen, Manu'
_publ_section_title
;
 N⋯I halogen bonding supported stabilization of a discrete
 pseudo-linear [I12]2−polyiodide
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1736
_journal_paper_doi               10.1039/C4CE01866D
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C20 H40 I4 N4, 2.67(I3)'
_chemical_formula_sum            'C20 H40 I12 N4'
_chemical_formula_weight         1859.36
_chemical_name_systematic
;
 ?
;
_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     iterative
_audit_creation_date             2014-08-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                102.188(3)
_cell_angle_beta                 92.217(2)
_cell_angle_gamma                106.349(3)
_cell_formula_units_Z            1
_cell_length_a                   8.8468(5)
_cell_length_b                   9.2378(4)
_cell_length_c                   13.5621(8)
_cell_measurement_temperature    123
_cell_volume                     1033.87(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13721
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.362
_exptl_absorpt_coefficient_mu    9.004
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0748 after correction.
The Ratio of minimum to maximum transmission is 0.7409.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'metallic blackish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.986
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.943
_refine_diff_density_min         -0.931
_refine_diff_density_rms         0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3625
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0408
_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)+10.7581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3129
_reflns_number_total             3625
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce01866d2.cif
_cod_data_source_block           2-I12_2-
_cod_depositor_comments
'Adding full bibliography for 7218347--7218353.cif.'
_cod_database_code               7218353
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-4
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B),
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
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
I1 I 1.26109(6) 1.15412(6) 0.43704(4) 0.02078(15) Uani 1 1 d .
I2 I 1.26950(6) 1.44483(6) 0.55229(5) 0.02209(15) Uani 1 1 d .
I3 I 0.79259(7) 1.19405(6) 0.33318(5) 0.02840(16) Uani 1 1 d .
I4 I 0.75544(6) 0.88399(6) 0.22313(4) 0.02064(15) Uani 1 1 d .
I5 I 0.71583(7) 0.55302(6) 0.11689(5) 0.02950(17) Uani 1 1 d .
I6 I 0.55654(7) 0.15658(7) 0.04097(5) 0.02891(16) Uani 1 1 d .
N1 N 1.2517(8) 0.8835(8) 0.3440(6) 0.0190(16) Uani 1 1 d .
N2 N 1.2379(7) 0.6052(7) 0.2631(5) 0.0168(15) Uani 1 1 d .
C1 C 1.3855(9) 0.8459(9) 0.3886(6) 0.0159(18) Uani 1 1 d .
H1A H 1.3774 0.8527 0.4619 0.019 Uiso 1 1 calc R
H1B H 1.4861 0.9218 0.3809 0.019 Uiso 1 1 calc R
C2 C 1.3859(9) 0.6818(9) 0.3360(7) 0.0190(19) Uani 1 1 d .
H2A H 1.4806 0.6870 0.2988 0.023 Uiso 1 1 calc R
H2B H 1.3894 0.6204 0.3872 0.023 Uiso 1 1 calc R
C3 C 1.1018(9) 0.7775(9) 0.3631(7) 0.0193(19) Uani 1 1 d .
H3A H 1.0111 0.7998 0.3311 0.023 Uiso 1 1 calc R
H3B H 1.0937 0.7947 0.4371 0.023 Uiso 1 1 calc R
C4 C 1.0954(9) 0.6076(9) 0.3199(7) 0.0207(19) Uani 1 1 d .
H4A H 1.0954 0.5537 0.3757 0.025 Uiso 1 1 calc R
H4B H 0.9971 0.5534 0.2736 0.025 Uiso 1 1 calc R
C5 C 1.2617(11) 0.8655(9) 0.2339(7) 0.025(2) Uani 1 1 d .
H5A H 1.3659 0.9309 0.2220 0.030 Uiso 1 1 calc R
H5B H 1.1782 0.9004 0.2040 0.030 Uiso 1 1 calc R
C6 C 1.2410(11) 0.6959(9) 0.1828(7) 0.024(2) Uani 1 1 d .
H6A H 1.1409 0.6526 0.1373 0.029 Uiso 1 1 calc R
H6B H 1.3296 0.6885 0.1416 0.029 Uiso 1 1 calc R
C7 C 1.2353(9) 0.4375(9) 0.2173(7) 0.022(2) Uani 1 1 d .
H7A H 1.3358 0.4398 0.1871 0.026 Uiso 1 1 calc R
H7B H 1.2318 0.3827 0.2729 0.026 Uiso 1 1 calc R
C8 C 1.1014(10) 0.3459(9) 0.1384(7) 0.022(2) Uani 1 1 d .
H8A H 1.1070 0.3940 0.0794 0.026 Uiso 1 1 calc R
H8B H 0.9992 0.3439 0.1662 0.026 Uiso 1 1 calc R
C9 C 1.1129(10) 0.1808(10) 0.1055(7) 0.026(2) Uani 1 1 d .
H9A H 1.2207 0.1856 0.0861 0.032 Uiso 1 1 calc R
H9B H 1.0973 0.1312 0.1638 0.032 Uiso 1 1 calc R
C10 C 0.9918(9) 0.0806(9) 0.0166(7) 0.0198(19) Uani 1 1 d .
H10A H 0.8838 0.0728 0.0366 0.024 Uiso 1 1 calc R
H10B H 1.0053 0.1313 -0.0412 0.024 Uiso 1 1 calc R
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'
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
N1 I1 I2 175.91(16) .
I3 I4 I5 177.24(3) .
C1 N1 I1 107.5(5) .
C1 N1 C3 109.2(6) .
C1 N1 C5 108.8(6) .
C3 N1 I1 106.9(5) .
C5 N1 I1 114.0(5) .
C5 N1 C3 110.3(7) .
C2 N2 C7 108.0(6) .
C4 N2 C2 109.1(6) .
C4 N2 C7 110.5(6) .
C6 N2 C2 108.5(6) .
C6 N2 C4 109.1(6) .
C6 N2 C7 111.6(6) .
N1 C1 H1A 109.6 .
N1 C1 H1B 109.6 .
N1 C1 C2 110.2(6) .
H1A C1 H1B 108.1 .
C2 C1 H1A 109.6 .
C2 C1 H1B 109.6 .
N2 C2 C1 109.1(6) .
N2 C2 H2A 109.9 .
N2 C2 H2B 109.9 .
C1 C2 H2A 109.9 .
C1 C2 H2B 109.9 .
H2A C2 H2B 108.3 .
N1 C3 H3A 109.6 .
N1 C3 H3B 109.6 .
N1 C3 C4 110.4(6) .
H3A C3 H3B 108.1 .
C4 C3 H3A 109.6 .
C4 C3 H3B 109.6 .
N2 C4 C3 108.6(6) .
N2 C4 H4A 110.0 .
N2 C4 H4B 110.0 .
C3 C4 H4A 110.0 .
C3 C4 H4B 110.0 .
H4A C4 H4B 108.3 .
N1 C5 H5A 109.6 .
N1 C5 H5B 109.6 .
N1 C5 C6 110.3(7) .
H5A C5 H5B 108.1 .
C6 C5 H5A 109.6 .
C6 C5 H5B 109.6 .
N2 C6 C5 109.1(7) .
N2 C6 H6A 109.9 .
N2 C6 H6B 109.9 .
C5 C6 H6A 109.9 .
C5 C6 H6B 109.9 .
H6A C6 H6B 108.3 .
N2 C7 H7A 108.4 .
N2 C7 H7B 108.4 .
H7A C7 H7B 107.4 .
C8 C7 N2 115.7(6) .
C8 C7 H7A 108.4 .
C8 C7 H7B 108.4 .
C7 C8 H8A 110.0 .
C7 C8 H8B 110.0 .
C7 C8 C9 108.5(7) .
H8A C8 H8B 108.4 .
C9 C8 H8A 110.0 .
C9 C8 H8B 110.0 .
C8 C9 H9A 108.9 .
C8 C9 H9B 108.9 .
H9A C9 H9B 107.8 .
C10 C9 C8 113.2(7) .
C10 C9 H9A 108.9 .
C10 C9 H9B 108.9 .
C9 C10 H10A 109.1 .
C9 C10 H10B 109.1 .
C10 C10 C9 112.3(9) 2_755
C10 C10 H10A 109.1 2_755
C10 C10 H10B 109.1 2_755
H10A C10 H10B 107.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 I2 2.7869(7) .
I1 N1 2.528(7) .
I3 I4 2.8577(8) .
I4 I5 3.0074(8) .
I6 I6 2.7444(12) 2_655
N1 C1 1.467(10) .
N1 C3 1.479(10) .
N1 C5 1.476(11) .
N2 C2 1.508(10) .
N2 C4 1.505(10) .
N2 C6 1.504(11) .
N2 C7 1.536(10) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1 C2 1.535(11) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C3 C4 1.539(11) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C5 C6 1.529(11) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C7 C8 1.489(11) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C8 C9 1.530(11) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C9 C10 1.526(12) .
C10 C10 1.512(15) 2_755
C10 H10A 0.9900 .
C10 H10B 0.9900 .
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
I1 N1 C1 C2 179.5(5) .
I1 N1 C3 C4 -173.2(6) .
I1 N1 C5 C6 -175.2(5) .
N1 C1 C2 N2 -6.2(9) .
N1 C3 C4 N2 -5.3(9) .
N1 C5 C6 N2 -7.2(9) .
N2 C7 C8 C9 -177.2(7) .
C1 N1 C3 C4 -57.1(9) .
C1 N1 C5 C6 64.8(8) .
C2 N2 C4 C3 62.1(8) .
C2 N2 C6 C5 -55.0(8) .
C2 N2 C7 C8 -176.6(7) .
C3 N1 C1 C2 63.8(9) .
C3 N1 C5 C6 -54.9(9) .
C4 N2 C2 C1 -55.9(8) .
C4 N2 C6 C5 63.7(8) .
C4 N2 C7 C8 64.2(9) .
C5 N1 C1 C2 -56.6(8) .
C5 N1 C3 C4 62.3(8) .
C6 N2 C2 C1 62.9(8) .
C6 N2 C4 C3 -56.2(8) .
C6 N2 C7 C8 -57.4(9) .
C7 N2 C2 C1 -176.0(7) .
C7 N2 C4 C3 -179.3(7) .
C7 N2 C6 C5 -173.9(6) .
C7 C8 C9 C10 -173.9(8) .
C8 C9 C10 C10 178.4(9) 2_755
