#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/93/1519367.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_1519367
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, Cl O4'
_chemical_formula_sum            'C10 H10 Cl I N2 O4'
_chemical_formula_weight         384.55
_chemical_name_systematic        '[bis(pyridine)iodine]perchlorate'
_chemical_properties_physical    Moisture-sensitive
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-21T22:00:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-03-23 deposited with the CCDC.
2015-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.273(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.2849(4)
_cell_length_b                   16.0628(3)
_cell_length_c                   14.7939(4)
_cell_measurement_reflns_used    4378
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      28.973
_cell_measurement_theta_min      2.214
_cell_volume                     2681.74(14)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies, 2013'
_computing_data_collection       'CrysAlisPro, Agilent Technologies, 2013'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies, 2013'
_computing_molecular_graphics    'Mercury (Macrae et al. 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2112)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_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  0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8696
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         1.963
_exptl_absorpt_coefficient_mu    2.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
        (compiled Feb  1 2013,16:14:44)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0410P)²+1.5970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                3865
_reflns_number_total             4960
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5sc01053e2.cif
_cod_data_source_block           2-I
_cod_depositor_comments
'Adding full bibliography for 1519367--1519381.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1519367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_calc_flag
I1A I -0.00285(2) 0.25548(2) 0.50666(2) 0.03333(9) Uani 1 d
N1A N 0.0702(2) 0.36244(15) 0.44900(17) 0.0344(6) Uani 1 d
N2A N -0.0774(2) 0.15211(15) 0.56837(17) 0.0349(6) Uani 1 d
C1A C 0.0724(3) 0.3600(2) 0.3595(2) 0.0426(8) Uani 1 d
H1A H 0.0453 0.3117 0.3198 0.051 Uiso 1 calc
C2A C 0.1138(3) 0.4272(3) 0.3246(3) 0.0552(10) Uani 1 d
H2A H 0.1157 0.425 0.2611 0.066 Uiso 1 calc
C3A C 0.1522(3) 0.4972(2) 0.3813(3) 0.0574(12) Uani 1 d
H3A H 0.1794 0.544 0.357 0.069 Uiso 1 calc
C4A C 0.1508(3) 0.4987(2) 0.4747(3) 0.0534(10) Uani 1 d
H4A H 0.1782 0.5461 0.516 0.064 Uiso 1 calc
C5A C 0.1091(3) 0.4304(2) 0.5055(2) 0.0414(7) Uani 1 d
H5A H 0.1075 0.4308 0.5692 0.05 Uiso 1 calc
C6A C -0.0926(3) 0.16491(19) 0.6519(2) 0.0389(7) Uani 1 d
H6A H -0.0726 0.2175 0.6835 0.047 Uiso 1 calc
C7A C -0.1366(3) 0.1033(2) 0.6931(2) 0.0467(8) Uani 1 d
H7A H -0.1469 0.1133 0.7525 0.056 Uiso 1 calc
C8A C -0.1652(3) 0.0277(2) 0.6472(3) 0.0460(8) Uani 1 d
H8A H -0.1953 -0.0156 0.6746 0.055 Uiso 1 calc
C9A C -0.1500(3) 0.0151(2) 0.5610(3) 0.0486(10) Uani 1 d
H9A H -0.1698 -0.0369 0.5278 0.058 Uiso 1 calc
C10A C -0.1055(3) 0.07880(19) 0.5234(2) 0.0416(8) Uani 1 d
H10A H -0.0947 0.0702 0.4639 0.05 Uiso 1 calc
I1B I 0.5 0.5 0.5 0.03437(10) Uani 1 d
N1B N 0.4278(2) 0.40425(14) 0.57375(17) 0.0328(6) Uani 1 d
C1B C 0.4267(3) 0.42016(19) 0.6623(2) 0.0398(7) Uani 1 d
H1B H 0.454 0.4726 0.6923 0.048 Uiso 1 calc
C2B C 0.3872(3) 0.3624(2) 0.7105(2) 0.0427(8) Uani 1 d
H2B H 0.3873 0.3747 0.7734 0.051 Uiso 1 calc
C3B C 0.3474(3) 0.28656(19) 0.6671(2) 0.0408(8) Uani 1 d
H3B H 0.321 0.2454 0.6999 0.049 Uiso 1 calc
C4B C 0.3466(3) 0.2713(2) 0.5757(3) 0.0404(8) Uani 1 d
H4B H 0.3177 0.2197 0.5437 0.048 Uiso 1 calc
C5B C 0.3876(3) 0.33088(18) 0.5307(2) 0.0360(7) Uani 1 d
H5B H 0.3876 0.3198 0.4676 0.043 Uiso 1 calc
I1C I 0.5 0 0.5 0.03134(10) Uani 1 d
N1C N 0.5681(2) 0.11401(15) 0.44988(17) 0.0335(6) Uani 1 d
C1C C 0.5844(3) 0.1133(2) 0.3658(2) 0.0415(8) Uani 1 d
H1C H 0.5668 0.0644 0.3265 0.05 Uiso 1 calc
C2C C 0.6266(3) 0.1827(2) 0.3356(3) 0.0524(9) Uani 1 d
H2C H 0.6389 0.1815 0.2761 0.063 Uiso 1 calc
C3C C 0.6509(3) 0.2539(2) 0.3920(3) 0.0565(12) Uani 1 d
H3C H 0.6785 0.3026 0.3712 0.068 Uiso 1 calc
C4C C 0.6346(3) 0.2535(2) 0.4794(3) 0.0519(10) Uani 1 d
H4C H 0.6522 0.3014 0.5202 0.062 Uiso 1 calc
C5C C 0.5927(3) 0.18259(19) 0.5058(2) 0.0420(8) Uani 1 d
H5C H 0.5806 0.1821 0.5654 0.05 Uiso 1 calc
Cl1A Cl 0.23676(7) 0.19606(5) 0.28107(5) 0.03861(19) Uani 1 d
O1A O 0.2014(2) 0.17411(14) 0.35977(17) 0.0618(7) Uani 1 d
O2A O 0.2430(3) 0.1240(2) 0.2295(3) 0.1126(14) Uani 1 d
O3A O 0.3479(3) 0.23674(19) 0.3198(2) 0.0715(9) Uani 1 d
O4A O 0.1523(3) 0.25098(19) 0.2165(2) 0.0811(11) Uani 1 d
Cl1B Cl 0.26306(7) 0.05775(5) 0.72515(5) 0.03847(19) Uani 1 d
O1B O 0.3102(2) 0.08372(14) 0.65472(16) 0.0569(7) Uani 1 d
O2B O 0.1427(2) 0.0341(2) 0.6768(2) 0.0699(8) Uani 1 d
O3B O 0.2776(3) 0.1226(2) 0.7928(2) 0.0978(11) Uani 1 d
O4B O 0.3283(3) -0.01304(18) 0.7766(2) 0.0734(9) Uani 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
N2A I1A N1A 177.72(9) .
C1A N1A C5A 120.0(3) .
C1A N1A I1A 121.3(2) .
C5A N1A I1A 118.7(2) .
C10A N2A C6A 119.7(3) .
C10A N2A I1A 121.1(2) .
C6A N2A I1A 119.2(2) .
N1A C1A C2A 120.2(3) .
N1A C1A H1A 119.9 .
C2A C1A H1A 119.9 .
C3A C2A C1A 120.2(3) .
C3A C2A H2A 119.9 .
C1A C2A H2A 119.9 .
C2A C3A C4A 119.1(3) .
C2A C3A H3A 120.4 .
C4A C3A H3A 120.4 .
C5A C4A C3A 118.1(3) .
C5A C4A H4A 120.9 .
C3A C4A H4A 120.9 .
N1A C5A C4A 122.3(3) .
N1A C5A H5A 118.9 .
C4A C5A H5A 118.9 .
N2A C6A C7A 121.4(3) .
N2A C6A H6A 119.3 .
C7A C6A H6A 119.3 .
C8A C7A C6A 119.1(3) .
C8A C7A H7A 120.5 .
C6A C7A H7A 120.5 .
C7A C8A C9A 119.2(3) .
C7A C8A H8A 120.4 .
C9A C8A H8A 120.4 .
C10A C9A C8A 119.1(3) .
C10A C9A H9A 120.4 .
C8A C9A H9A 120.4 .
N2A C10A C9A 121.5(3) .
N2A C10A H10A 119.3 .
C9A C10A H10A 119.3 .
N1B I1B N1B 180 3_666
C5B N1B C1B 119.3(3) .
C5B N1B I1B 120.72(19) .
C1B N1B I1B 120.0(2) .
N1B C1B C2B 121.5(3) .
N1B C1B H1B 119.3 .
C2B C1B H1B 119.3 .
C1B C2B C3B 119.4(3) .
C1B C2B H2B 120.3 .
C3B C2B H2B 120.3 .
C2B C3B C4B 118.9(3) .
C2B C3B H3B 120.6 .
C4B C3B H3B 120.6 .
C5B C4B C3B 119.6(3) .
C5B C4B H4B 120.2 .
C3B C4B H4B 120.2 .
N1B C5B C4B 121.4(3) .
N1B C5B H5B 119.3 .
C4B C5B H5B 119.3 .
N1C I1C N1C 180 3_656
C1C N1C C5C 120.1(3) .
C1C N1C I1C 120.7(2) .
C5C N1C I1C 119.2(2) .
N1C C1C C2C 120.7(3) .
N1C C1C H1C 119.7 .
C2C C1C H1C 119.7 .
C3C C2C C1C 119.7(3) .
C3C C2C H2C 120.2 .
C1C C2C H2C 120.2 .
C2C C3C C4C 119.0(3) .
C2C C3C H3C 120.5 .
C4C C3C H3C 120.5 .
C5C C4C C3C 118.7(3) .
C5C C4C H4C 120.6 .
C3C C4C H4C 120.6 .
N1C C5C C4C 121.8(3) .
N1C C5C H5C 119.1 .
C4C C5C H5C 119.1 .
O2A Cl1A O4A 109.4(2) .
O2A Cl1A O3A 110.4(2) .
O4A Cl1A O3A 108.7(2) .
O2A Cl1A O1A 109.65(17) .
O4A Cl1A O1A 108.96(17) .
O3A Cl1A O1A 109.72(17) .
O3B Cl1B O2B 111.82(19) .
O3B Cl1B O4B 108.9(2) .
O2B Cl1B O4B 108.07(17) .
O3B Cl1B O1B 109.05(16) .
O2B Cl1B O1B 110.52(16) .
O4B Cl1B O1B 108.38(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1A N2A 2.256(2) .
I1A N1A 2.256(2) .
N1A C1A 1.335(4) .
N1A C5A 1.343(4) .
N2A C10A 1.330(4) .
N2A C6A 1.336(4) .
C1A C2A 1.377(5) .
C1A H1A 0.95 .
C2A C3A 1.370(5) .
C2A H2A 0.95 .
C3A C4A 1.390(6) .
C3A H3A 0.95 .
C4A C5A 1.364(4) .
C4A H4A 0.95 .
C5A H5A 0.95 .
C6A C7A 1.381(4) .
C6A H6A 0.95 .
C7A C8A 1.367(5) .
C7A H7A 0.95 .
C8A C9A 1.376(5) .
C8A H8A 0.95 .
C9A C10A 1.377(5) .
C9A H9A 0.95 .
C10A H10A 0.95 .
I1B N1B 2.260(2) .
I1B N1B 2.260(2) 3_666
N1B C5B 1.338(4) .
N1B C1B 1.339(4) .
C1B C2B 1.371(4) .
C1B H1B 0.95 .
C2B C3B 1.374(4) .
C2B H2B 0.95 .
C3B C4B 1.370(4) .
C3B H3B 0.95 .
C4B C5B 1.371(4) .
C4B H4B 0.95 .
C5B H5B 0.95 .
I1C N1C 2.257(2) .
I1C N1C 2.257(2) 3_656
N1C C1C 1.336(4) .
N1C C5C 1.338(4) .
C1C C2C 1.376(4) .
C1C H1C 0.95 .
C2C C3C 1.377(5) .
C2C H2C 0.95 .
C3C C4C 1.384(6) .
C3C H3C 0.95 .
C4C C5C 1.369(4) .
C4C H4C 0.95 .
C5C H5C 0.95 .
Cl1A O2A 1.405(3) .
Cl1A O4A 1.409(3) .
Cl1A O3A 1.415(3) .
Cl1A O1A 1.438(2) .
Cl1B O3B 1.406(3) .
Cl1B O2B 1.416(3) .
Cl1B O4B 1.426(3) .
Cl1B O1B 1.439(2) .
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
C5A N1A C1A C2A -0.4(4)
I1A N1A C1A C2A 177.8(2)
N1A C1A C2A C3A -0.4(5)
C1A C2A C3A C4A 1.2(6)
C2A C3A C4A C5A -1.0(6)
C1A N1A C5A C4A 0.5(5)
I1A N1A C5A C4A -177.8(3)
C3A C4A C5A N1A 0.2(5)
C10A N2A C6A C7A 0.3(5)
I1A N2A C6A C7A -179.3(2)
N2A C6A C7A C8A 0.0(5)
C6A C7A C8A C9A -0.3(5)
C7A C8A C9A C10A 0.4(5)
C6A N2A C10A C9A -0.2(5)
I1A N2A C10A C9A 179.4(2)
C8A C9A C10A N2A -0.2(5)
C5B N1B C1B C2B 1.1(4)
I1B N1B C1B C2B -177.8(2)
N1B C1B C2B C3B -0.2(5)
C1B C2B C3B C4B -1.1(5)
C2B C3B C4B C5B 1.4(5)
C1B N1B C5B C4B -0.7(4)
I1B N1B C5B C4B 178.2(2)
C3B C4B C5B N1B -0.6(5)
C5C N1C C1C C2C 0.1(4)
I1C N1C C1C C2C -179.6(2)
N1C C1C C2C C3C -0.8(5)
C1C C2C C3C C4C 1.3(6)
C2C C3C C4C C5C -1.2(6)
C1C N1C C5C C4C 0.1(5)
I1C N1C C5C C4C 179.7(3)
C3C C4C C5C N1C 0.5(5)
