#------------------------------------------------------------------------------
#$Date: 2015-07-10 23:18:58 +0300 (Fri, 10 Jul 2015) $
#$Revision: 143323 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/93/1519372.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_1519372
loop_
_publ_author_name
'Bedin, Michele'
'Karim, Alavi'
'Reitti, Marcus'
'Carlsson, Anna-Carin C.'
'Topić, Filip'
'Cetina, Mario'
'Pan, Fangfang'
'Havel, Vaclav'
'Al-Ameri, Fatima'
'Sindelar, Vladimir'
'Rissanen, Kari'
'Gräfenstein, Jürgen'
'Erdélyi, Máté'
_publ_section_title
;
 Counterion influence on the N--I--N halogen bond
;
_journal_issue                   7
_journal_name_full               'Chem. Sci.'
_journal_page_first              3746
_journal_paper_doi               10.1039/C5SC01053E
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C10 H10 I N2 +, N O3 -'
_chemical_formula_sum            'C10 H10 I N3 O3'
_chemical_formula_weight         347.11
_chemical_name_systematic        '[bis(pyridine)iodine]nitrate'
_chemical_properties_physical    Moisture-sensitive
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-03-23 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                99.491(4)
_cell_angle_beta                 94.725(4)
_cell_angle_gamma                117.637(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0864(3)
_cell_length_b                   7.4613(3)
_cell_length_c                   13.5366(6)
_cell_measurement_reflns_used    1672
_cell_measurement_temperature    173.0(1)
_cell_measurement_theta_max      29.2710
_cell_measurement_theta_min      5.8090
_cell_volume                     614.97(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      173.0(1)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.020
_diffrn_reflns_av_unetI/netI     0.030
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7724
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         29.410
_diffrn_reflns_theta_min         3.167
_exptl_absorpt_coefficient_mu    2.609
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
 a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.875
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.152
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.796
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         5116
_refine_ls_number_restraints     142
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0332
_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)+(0.0621P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1043
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3322
_reflns_number_total             5116
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5sc01053e2.cif
_cod_data_source_block           7-I
_cod_depositor_comments
'Adding full bibliography for 1519367--1519381.cif.'
_cod_database_code               1519372
_shelx_shelxl_version_number     2014/7
_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   0.520
_shelx_estimated_absorpt_t_max   0.693
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
C2A C 0.5069(8) 0.7337(9) 0.0060(5) 0.0568(15) Uani 1 1 d . . . . .
H2A H 0.5130 0.6552 -0.0554 0.068 Uiso 1 1 calc R U . . .
C3A C 0.3147(10) 0.6666(12) 0.0420(7) 0.072(2) Uani 1 1 d . . . . .
H3A H 0.1890 0.5434 0.0052 0.087 Uiso 1 1 calc R U . . .
C4A C 0.3050(11) 0.7768(13) 0.1305(6) 0.077(2) Uani 1 1 d . . . . .
H4A H 0.1742 0.7295 0.1568 0.093 Uiso 1 1 calc R U . . .
C5A C 0.4869(12) 0.9571(13) 0.1810(5) 0.0710(19) Uani 1 1 d . . . . .
H5A H 0.4824 1.0377 0.2420 0.085 Uiso 1 1 calc R U . . .
C6A C 0.6810(9) 1.0221(10) 0.1418(4) 0.0602(15) Uani 1 1 d . . . . .
H6A H 0.8079 1.1467 0.1763 0.072 Uiso 1 1 calc R U . . .
N1A N 0.6851(6) 0.9080(7) 0.0563(3) 0.0448(10) Uani 1 1 d . . . . .
I1A I 1.0000 1.0000 0.0000 0.03727(14) Uani 1 2 d S . P . .
C2B C 0.7539(8) 0.4812(8) 0.5124(4) 0.0451(11) Uani 1 1 d . . . . .
H2B H 0.7763 0.4340 0.4471 0.054 Uiso 1 1 calc R U . . .
C3B C 0.8457(9) 0.6903(9) 0.5538(5) 0.0538(14) Uani 1 1 d . . . . .
H3B H 0.9325 0.7883 0.5176 0.065 Uiso 1 1 calc R U . . .
C4B C 0.8107(10) 0.7568(9) 0.6485(5) 0.0599(17) Uani 1 1 d . . . . .
H4B H 0.8754 0.9013 0.6783 0.072 Uiso 1 1 calc R U . . .
C5B C 0.6833(10) 0.6153(9) 0.6992(4) 0.0629(15) Uani 1 1 d . . . . .
H5B H 0.6560 0.6581 0.7640 0.075 Uiso 1 1 calc R U . . .
C6B C 0.5962(9) 0.4095(9) 0.6533(4) 0.0522(13) Uani 1 1 d . . . . .
H6B H 0.5050 0.3087 0.6870 0.063 Uiso 1 1 calc R U . . .
N1B N 0.6343(6) 0.3450(5) 0.5633(3) 0.0377(8) Uani 1 1 d . . . . .
I1B I 0.5000 0.0000 0.5000 0.03573(14) Uani 1 2 d S . P . .
N1C N 0.8507(7) 0.6137(6) 0.2591(3) 0.0523(11) Uani 1 1 d D U . . .
O1C O 0.7944(11) 0.6762(13) 0.1931(5) 0.070(2) Uani 0.713(9) 1 d D U P A 1
O2C O 0.9850(11) 0.7261(10) 0.3359(5) 0.093(3) Uani 0.713(9) 1 d D U P A 1
O3C O 0.7763(16) 0.4227(10) 0.2548(6) 0.094(3) Uani 0.713(9) 1 d D U P A 1
O4C O 0.921(3) 0.521(3) 0.2963(11) 0.076(4) Uani 0.287(9) 1 d D U P A 2
O5C O 0.742(3) 0.550(3) 0.1714(9) 0.087(5) Uani 0.287(9) 1 d D U P A 2
O6C O 0.871(3) 0.7815(19) 0.3068(14) 0.098(5) Uani 0.287(9) 1 d D U P A 2
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'
O O 0.0106 0.0060 '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
N1A C2A C3A 120.8(6) . .
N1A C2A H2A 119.6 . .
C3A C2A H2A 119.6 . .
C4A C3A C2A 120.0(7) . .
C4A C3A H3A 120.0 . .
C2A C3A H3A 120.0 . .
C3A C4A C5A 119.0(6) . .
C3A C4A H4A 120.5 . .
C5A C4A H4A 120.5 . .
C4A C5A C6A 119.6(6) . .
C4A C5A H5A 120.2 . .
C6A C5A H5A 120.2 . .
N1A C6A C5A 119.6(6) . .
N1A C6A H6A 120.2 . .
C5A C6A H6A 120.2 . .
C6A N1A C2A 121.0(5) . .
C6A N1A I1A 119.5(4) . .
C2A N1A I1A 119.5(3) . .
N1A I1A N1A 180.0 2_775 .
N1B C2B C3B 120.2(5) . .
N1B C2B H2B 119.9 . .
C3B C2B H2B 119.9 . .
C2B C3B C4B 119.3(6) . .
C2B C3B H3B 120.3 . .
C4B C3B H3B 120.3 . .
C5B C4B C3B 120.0(5) . .
C5B C4B H4B 120.0 . .
C3B C4B H4B 120.0 . .
C4B C5B C6B 117.5(6) . .
C4B C5B H5B 121.2 . .
C6B C5B H5B 121.2 . .
N1B C6B C5B 122.5(6) . .
N1B C6B H6B 118.7 . .
C5B C6B H6B 118.7 . .
C2B N1B C6B 120.3(4) . .
C2B N1B I1B 120.3(3) . .
C6B N1B I1B 119.3(3) . .
N1B I1B N1B 180.0 . 2_656
O1C N1C O2C 124.2(6) . .
O4C N1C O5C 123.5(10) . .
O4C N1C O6C 122.0(11) . .
O5C N1C O6C 114.3(10) . .
O1C N1C O3C 122.1(6) . .
O2C N1C O3C 113.8(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2A N1A 1.339(7) .
C2A C3A 1.379(7) .
C2A H2A 0.9500 .
C3A C4A 1.362(11) .
C3A H3A 0.9500 .
C4A C5A 1.372(11) .
C4A H4A 0.9500 .
C5A C6A 1.412(7) .
C5A H5A 0.9500 .
C6A N1A 1.330(6) .
C6A H6A 0.9500 .
N1A I1A 2.250(4) .
I1A N1A 2.250(4) 2_775
C2B N1B 1.324(6) .
C2B C3B 1.371(8) .
C2B H2B 0.9500 .
C3B C4B 1.381(10) .
C3B H3B 0.9500 .
C4B C5B 1.363(9) .
C4B H4B 0.9500 .
C5B C6B 1.366(7) .
C5B H5B 0.9500 .
C6B N1B 1.331(6) .
C6B H6B 0.9500 .
N1B I1B 2.265(3) .
I1B N1B 2.265(4) 2_656
N1C O4C 1.170(8) .
N1C O1C 1.194(6) .
N1C O2C 1.225(6) .
N1C O5C 1.246(9) .
N1C O6C 1.248(8) .
N1C O3C 1.258(6) .
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
N1A C2A C3A C4A -0.7(9)
C2A C3A C4A C5A 1.7(9)
C3A C4A C5A C6A -1.4(9)
C4A C5A C6A N1A 0.1(8)
C5A C6A N1A C2A 0.9(7)
C5A C6A N1A I1A -175.7(4)
C3A C2A N1A C6A -0.6(7)
C3A C2A N1A I1A 176.0(4)
N1B C2B C3B C4B -0.4(7)
C2B C3B C4B C5B -1.0(8)
C3B C4B C5B C6B 0.7(8)
C4B C5B C6B N1B 1.1(8)
C3B C2B N1B C6B 2.2(7)
C3B C2B N1B I1B -176.1(3)
C5B C6B N1B C2B -2.6(7)
C5B C6B N1B I1B 175.7(4)
