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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/49/4504988.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.
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data_4504988
loop_
_publ_author_name
'Padgett, Clifford W.'
'Walsh, Rosa D.'
'Drake, Gregory W.'
'Hanks, Timothy W.'
'Pennington, William T.'
_publ_section_title
;
 New Conformations and Binding Modes in Halogen-Bonded and Ionic Complexes
 of 2,3,5,6-Tetra(2‘-pyridyl)pyrazine
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              745
_journal_paper_doi               10.1021/cg049730z
_journal_volume                  5
_journal_year                    2005
_chemical_formula_moiety         'C24 H20 N6 4+, 2I 1-, (I3 1-)2'
_chemical_formula_sum            'C24 H20 I8 N6'
_chemical_formula_weight         1407.66
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.230(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.895(2)
_cell_length_b                   11.682(2)
_cell_length_c                   12.957(2)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.8
_cell_measurement_theta_min      14.1
_cell_volume                     1795.6(5)
_computing_cell_refinement       'Siemens P3 software (1989)'
_computing_data_collection       'Siemens P3 software (1989)'
_computing_data_reduction        'SHELXTL,VERSION 6.10 Sheldick (2000)'
_computing_molecular_graphics    'SHELXTL,VERSION 6.10'
_computing_publication_material  'SHELXTL,VERSION 6.10'
_computing_structure_refinement  'SHELXTL,VERSION 6.10'
_computing_structure_solution    'SHELXTL,VERSION 6.10'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nicolet R3mV diffractometer'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_detector       'Nicolet R3mV serial detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2500
_diffrn_reflns_theta_full        22.56
_diffrn_reflns_theta_max         22.56
_diffrn_reflns_theta_min         2.24
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    6.933
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       0.00090(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0233
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0128P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0397
_refine_ls_wR_factor_ref         0.0406
_reflns_number_gt                1769
_reflns_number_total             2350
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg049730zsi20040802_040247.cif
_cod_data_source_block           '[tppz(H)4](I)2(I3)2'
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4504988
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.28607(4) 0.12034(4) 0.59503(3) 0.05104(15) Uani 1 1 d .
I2 I 0.18845(4) 0.52955(4) 0.54653(4) 0.05553(16) Uani 1 1 d .
I3 I 0.19833(4) 0.39945(4) 0.35189(4) 0.04824(14) Uani 1 1 d .
I4 I 0.21927(5) 0.27826(5) 0.16046(4) 0.0761(2) Uani 1 1 d .
N1 N 0.4859(4) 0.3900(4) 0.5339(3) 0.0279(12) Uani 1 1 d .
N2 N 0.4217(4) 0.3457(4) 0.7248(4) 0.0406(14) Uani 1 1 d .
H2A H 0.3828 0.3166 0.6727 0.049 Uiso 1 1 calc R
N3 N 0.4527(4) 0.2126(4) 0.4007(4) 0.0356(13) Uani 1 1 d .
H3A H 0.4131 0.2185 0.4533 0.043 Uiso 1 1 calc R
C1 C 0.4880(5) 0.4767(5) 0.6001(4) 0.0283(15) Uani 1 1 d .
C2 C 0.5000(5) 0.4104(5) 0.4341(4) 0.0282(15) Uani 1 1 d .
C3 C 0.4845(5) 0.4381(5) 0.7097(4) 0.0285(15) Uani 1 1 d .
C4 C 0.5485(5) 0.4821(6) 0.7912(5) 0.0407(17) Uani 1 1 d .
H4A H 0.5936 0.5458 0.7825 0.049 Uiso 1 1 calc R
C5 C 0.5458(6) 0.4312(6) 0.8874(5) 0.051(2) Uani 1 1 d .
H5A H 0.5902 0.4601 0.9436 0.061 Uiso 1 1 calc R
C6 C 0.4785(7) 0.3390(7) 0.8998(6) 0.063(2) Uani 1 1 d .
H6A H 0.4750 0.3057 0.9647 0.076 Uiso 1 1 calc R
C7 C 0.4170(7) 0.2966(6) 0.8175(5) 0.061(2) Uani 1 1 d .
H7A H 0.3711 0.2331 0.8250 0.073 Uiso 1 1 calc R
C8 C 0.5081(5) 0.3067(5) 0.3707(4) 0.0313(15) Uani 1 1 d .
C9 C 0.5741(5) 0.2932(5) 0.2888(4) 0.0396(17) Uani 1 1 d .
H9A H 0.6157 0.3547 0.2667 0.047 Uiso 1 1 calc R
C10 C 0.5789(6) 0.1892(6) 0.2390(5) 0.0510(19) Uani 1 1 d .
H10A H 0.6232 0.1811 0.1832 0.061 Uiso 1 1 calc R
C11 C 0.5192(6) 0.0987(6) 0.2712(5) 0.0498(18) Uani 1 1 d .
H11A H 0.5218 0.0288 0.2370 0.060 Uiso 1 1 calc R
C12 C 0.4559(5) 0.1104(6) 0.3533(5) 0.0495(18) Uani 1 1 d .
H12A H 0.4153 0.0487 0.3765 0.059 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'
N N 0.0061 0.0033 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 0 -4
0 2 -3
2 2 1
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
I4 I3 I2 176.96(2) . .
C1 N1 C2 119.4(5) . .
C3 N2 C7 122.7(6) . .
C12 N3 C8 124.0(5) . .
N1 C1 C2 120.8(5) . 3_666
N1 C1 C3 112.6(5) . .
C2 C1 C3 126.5(5) 3_666 .
N1 C2 C1 119.7(5) . 3_666
N1 C2 C8 114.3(5) . .
C1 C2 C8 125.9(5) 3_666 .
N2 C3 C4 118.7(6) . .
N2 C3 C1 116.0(5) . .
C4 C3 C1 124.9(6) . .
C3 C4 C5 119.3(6) . .
C6 C5 C4 120.0(7) . .
C7 C6 C5 119.3(7) . .
N2 C7 C6 119.9(7) . .
N3 C8 C9 116.5(6) . .
N3 C8 C2 117.1(5) . .
C9 C8 C2 126.2(6) . .
C8 C9 C10 120.5(6) . .
C11 C10 C9 120.1(6) . .
C12 C11 C10 119.8(6) . .
N3 C12 C11 119.0(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I2 I3 2.9543(8) .
I3 I4 2.8826(8) .
N1 C1 1.326(7) .
N1 C2 1.337(6) .
N2 C3 1.335(7) .
N2 C7 1.336(7) .
N3 C12 1.344(7) .
N3 C8 1.353(7) .
C1 C2 1.402(8) 3_666
C1 C3 1.494(7) .
C2 C1 1.402(8) 3_666
C2 C8 1.471(8) .
C3 C4 1.356(8) .
C4 C5 1.384(8) .
C5 C6 1.358(9) .
C6 C7 1.343(9) .
C8 C9 1.375(7) .
C9 C10 1.379(8) .
C10 C11 1.356(9) .
C11 C12 1.355(8) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A I1 0.86 2.72 3.459(5) 144.2
N3 H3A I1 0.86 2.72 3.488(5) 150.1
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_1
_geom_torsion_site_symmetry_4
C2 N1 C1 C2 2.7(9) . 3_666
C2 N1 C1 C3 -173.4(5) . .
C1 N1 C2 C1 -2.7(9) . 3_666
C1 N1 C2 C8 173.8(5) . .
C7 N2 C3 C4 1.9(9) . .
C7 N2 C3 C1 175.1(6) . .
N1 C1 C3 N2 -35.6(7) . .
C2 C1 C3 N2 148.7(6) 3_666 .
N1 C1 C3 C4 137.2(6) . .
C2 C1 C3 C4 -38.5(9) 3_666 .
N2 C3 C4 C5 -0.8(9) . .
C1 C3 C4 C5 -173.4(6) . .
C3 C4 C5 C6 -0.9(10) . .
C4 C5 C6 C7 1.6(11) . .
C3 N2 C7 C6 -1.2(11) . .
C5 C6 C7 N2 -0.6(11) . .
C12 N3 C8 C9 -2.3(9) . .
C12 N3 C8 C2 -177.2(6) . .
N1 C2 C8 N3 29.3(8) . .
C1 C2 C8 N3 -154.5(6) 3_666 .
N1 C2 C8 C9 -145.0(6) . .
C1 C2 C8 C9 31.2(10) 3_666 .
N3 C8 C9 C10 2.1(9) . .
C2 C8 C9 C10 176.5(6) . .
C8 C9 C10 C11 -0.6(11) . .
C9 C10 C11 C12 -0.8(11) . .
C8 N3 C12 C11 1.0(10) . .
C10 C11 C12 N3 0.7(11) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145685
