#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/03/2240351.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2240351
loop_
_publ_author_name
'Guino-o, Marites A.'
'Folstad, Matthew J.'
'Janzen, Daron E.'
_publ_section_title
;
 Crystal structures of
 2,6-bis[(1H-1,2,4-triazol-1-yl)methyl]pyridine and
 1,1-[pyridine-2,6-diylbis(methylene)]bis(4-methyl-1H-1,2,4-triazol-4-ium)
 iodide triiodide
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              128
_journal_page_last               132
_journal_paper_doi               10.1107/S2056989014027881
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C13 H17 N7 2+, I3 -, I -'
_chemical_formula_moiety         'C13 H17 N7 2+, I3 -, I -'
_chemical_formula_sum            'C13 H17 I4 N7'
_chemical_formula_weight         778.94
_chemical_name_systematic
'1,1-[Pyridine-2,6-diylbis(methylene)]bis(4-methyl-1H-1,2,4-triazol-4-ium) iodide triiodide'
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 102.648(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.784(3)
_cell_length_b                   10.010(3)
_cell_length_c                   16.709(4)
_cell_measurement_reflns_used    10090
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      3.02
_cell_volume                     2249.5(10)
_computing_cell_refinement
;
CrystalClear-SM Expert (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert (Rigaku, 2011)
;
_computing_molecular_graphics
;
CrystalStructure (Rigaku, 2010)
;
_computing_publication_material
;
CrystalStructure (Rigaku, 2010)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11638
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.013
_exptl_absorpt_coefficient_mu    5.551
_exptl_absorpt_correction_T_max  0.607
_exptl_absorpt_correction_T_min  0.322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(REQAB; Rigaku, 1998)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_refine_diff_density_max         1.089
_refine_diff_density_min         -1.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0359
_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)+(0.0241P)²+14.4966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0799
_reflns_number_gt                2303
_reflns_number_total             2712
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2322sup1.cif
_cod_data_source_block           II
_cod_database_code               2240351
_cod_database_fobs_code          2240351
#BEGIN Tags that were not found in dictionaries:
_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   0.254
_shelx_estimated_absorpt_t_max   0.635
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.64670(4) 0.5000 0.08917(4) 0.04623(16) Uani d 0.9761(9) A 1
I I2 0.60699(4) 0.5000 0.25579(3) 0.03549(14) Uani d 0.9761(9) A 1
I I3 0.55437(5) 0.5000 0.41333(4) 0.05505(18) Uani d 0.9761(9) A 1
I I1' 0.6681(18) 0.5000 0.0437(17) 0.04623(16) Uani d 0.0239(9) A 2
I I2' 0.6331(15) 0.5000 0.2138(16) 0.03549(14) Uani d 0.0239(9) A 2
I I3' 0.577(2) 0.5000 0.3681(17) 0.05505(18) Uani d 0.0239(9) A 2
I I4 0.62747(3) 0.0000 0.39551(3) 0.03401(13) Uani d 1 . .
N N1 0.8485(3) 0.2640(4) 0.3182(2) 0.0330(9) Uani d 1 . .
N N2 0.7994(4) 0.1816(5) 0.1944(3) 0.0497(12) Uani d 1 . .
N N3 0.8876(3) 0.2471(4) 0.2021(2) 0.0338(9) Uani d 1 . .
N N4 0.9323(4) 0.5000 0.1270(3) 0.0324(12) Uani d 1 . .
C C1 0.8505(4) 0.2959(7) 0.4053(3) 0.0487(14) Uani d 1 . .
H H1A 0.8496 0.2128 0.4362 0.058 Uiso calc 1 . .
H H1B 0.7921 0.3498 0.4086 0.058 Uiso calc 1 . .
H H1C 0.9110 0.3461 0.4288 0.058 Uiso calc 1 . .
C C2 0.9165(4) 0.2969(5) 0.2765(3) 0.0360(11) Uani d 1 . .
H H2 0.9752 0.3472 0.2965 0.043 Uiso calc 1 . .
C C3 0.7785(4) 0.1942(6) 0.2659(3) 0.0443(13) Uani d 1 . .
H H3 0.7205 0.1583 0.2798 0.053 Uiso calc 1 . .
C C4 0.9370(5) 0.2575(6) 0.1327(3) 0.0510(15) Uani d 1 . .
H H4A 0.9171 0.1807 0.0953 0.061 Uiso calc 1 . .
H H4B 1.0099 0.2534 0.1535 0.061 Uiso calc 1 . .
C C5 0.9101(4) 0.3866(5) 0.0855(3) 0.0366(11) Uani d 1 . .
C C6 0.8671(4) 0.3811(5) 0.0021(3) 0.0391(12) Uani d 1 . .
H H6 0.8522 0.2978 -0.0251 0.047 Uiso calc 1 . .
C C7 0.8468(6) 0.5000 -0.0403(4) 0.0421(18) Uani d 1 . .
H H7 0.8192 0.5000 -0.0976 0.051 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
I3 I2 I1 . 176.19(2)
I3' I2' I1' . 173.8(10)
C2 N1 C3 . 106.0(4)
C2 N1 C1 . 126.8(4)
C3 N1 C1 . 127.2(4)
C3 N2 N3 . 103.9(4)
C2 N3 N2 . 110.5(4)
C2 N3 C4 . 128.4(5)
N2 N3 C4 . 121.1(4)
C5 N4 C5 6_565 117.2(6)
N1 C1 H1A . 109.5
N1 C1 H1B . 109.5
H1A C1 H1B . 109.5
N1 C1 H1C . 109.5
H1A C1 H1C . 109.5
H1B C1 H1C . 109.5
N3 C2 N1 . 107.5(4)
N3 C2 H2 . 126.3
N1 C2 H2 . 126.3
N2 C3 N1 . 112.1(5)
N2 C3 H3 . 123.9
N1 C3 H3 . 123.9
N3 C4 C5 . 111.6(4)
N3 C4 H4A . 109.3
C5 C4 H4A . 109.3
N3 C4 H4B . 109.3
C5 C4 H4B . 109.3
H4A C4 H4B . 108.0
N4 C5 C6 . 123.7(5)
N4 C5 C4 . 117.0(5)
C6 C5 C4 . 119.3(5)
C7 C6 C5 . 118.3(5)
C7 C6 H6 . 120.9
C5 C6 H6 . 120.9
C6 C7 C6 6_565 118.9(7)
C6 C7 H7 6_565 120.5
C6 C7 H7 . 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 I2 . 2.9524(10)
I2 I3 . 2.8796(10)
I1' I2' . 2.98(3)
I2' I3' . 2.85(4)
N1 C2 . 1.326(6)
N1 C3 . 1.347(6)
N1 C1 . 1.485(6)
N2 C3 . 1.295(7)
N2 N3 . 1.362(6)
N3 C2 . 1.317(6)
N3 C4 . 1.471(6)
N4 C5 6_565 1.331(6)
N4 C5 . 1.331(6)
C1 H1A . 0.9800
C1 H1B . 0.9800
C1 H1C . 0.9800
C2 H2 . 0.9500
C3 H3 . 0.9500
C4 C5 . 1.517(7)
C4 H4A . 0.9900
C4 H4B . 0.9900
C5 C6 . 1.391(7)
C6 C7 . 1.381(6)
C6 H6 . 0.9500
C7 C6 6_565 1.381(6)
C7 H7 . 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3 H3 I4 . 0.95 3.00 3.844(5) 149
C2 H2 I4 3 0.95 2.82 3.744(5) 164
C4 H4B I2 3_545 0.99 3.18 3.775(6) 120
C4 H4B I2' 3_545 0.99 3.10 3.766(15) 126
C6 H6 I1 7_655 0.95 3.17 4.097(5) 166
C6 H6 I1' 7_655 0.95 3.00 3.900(8) 158
C4 H4A I1' 7_655 0.99 2.98 3.94(2) 166
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C3 N2 N3 C2 . . -0.3(6)
C3 N2 N3 C4 . . -179.2(5)
N2 N3 C2 N1 . . 0.5(6)
C4 N3 C2 N1 . . 179.3(5)
C3 N1 C2 N3 . . -0.4(6)
C1 N1 C2 N3 . . 178.6(5)
N3 N2 C3 N1 . . 0.0(6)
C2 N1 C3 N2 . . 0.3(6)
C1 N1 C3 N2 . . -178.8(5)
C2 N3 C4 C5 . . -84.4(7)
N2 N3 C4 C5 . . 94.3(6)
C5 N4 C5 C6 6_565 . 1.0(10)
C5 N4 C5 C4 6_565 . 179.1(4)
N3 C4 C5 N4 . . 59.2(7)
N3 C4 C5 C6 . . -122.7(5)
N4 C5 C6 C7 . . 0.4(9)
C4 C5 C6 C7 . . -177.6(6)
C5 C6 C7 C6 . 6_565 -1.8(11)
