#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:32:33 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179584 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/49/4504987.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_4504987
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 H18 N6 2+, (I2)2, (I3 1-)2'
_chemical_formula_sum            'C24 H18 I10 N6'
_chemical_formula_weight         1659.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           48
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2bc'
_symmetry_space_group_name_H-M   'P n n n :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.0741(11)
_cell_length_b                   11.6272(13)
_cell_length_c                   15.2196(13)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.0
_cell_measurement_theta_min      13.5
_cell_volume                     1959.7(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1299
_diffrn_reflns_theta_full        22.54
_diffrn_reflns_theta_max         22.54
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    7.930
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.812
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             1468
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.00279(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0243
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0197P)²+0.6011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0451
_refine_ls_wR_factor_ref         0.0465
_reflns_number_gt                986
_reflns_number_total             1299
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg049730zsi20040802_040229.cif
_cod_data_source_block           '[tppz(H)2](I2.I3)2'
_cod_original_sg_symbol_H-M      Pnnn
_cod_database_code               4504987
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x-1/2, -y, z-1/2'
'-x, 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 0.2500 0.55263(5) 0.2500 0.0467(2) Uani 1 2 d S
I2 I 0.11744(4) 0.53912(4) 0.08357(3) 0.05615(18) Uani 1 1 d .
I3 I -0.14572(5) 0.54197(5) 0.19951(3) 0.0758(2) Uani 1 1 d .
N1 N 0.1291(6) 0.2500 0.2500 0.0315(16) Uani 1 2 d S
N2 N 0.1423(5) 0.2096(4) 0.0178(3) 0.0436(14) Uani 1 1 d .
H2A H 0.2146 0.2325 0.0068 0.052 Uiso 0.50 1 calc PR
C1 C 0.1856(5) 0.2413(5) 0.1731(4) 0.0343(14) Uani 1 1 d .
C2 C 0.1042(6) 0.2078(5) 0.0999(4) 0.0374(16) Uani 1 1 d .
C3 C -0.0129(6) 0.1740(6) 0.1172(4) 0.0541(19) Uani 1 1 d .
H3A H -0.0411 0.1721 0.1748 0.065 Uiso 1 1 calc R
C4 C -0.0875(6) 0.1431(7) 0.0491(5) 0.064(2) Uani 1 1 d .
H4A H -0.1667 0.1209 0.0603 0.077 Uiso 1 1 calc R
C5 C -0.0447(6) 0.1452(6) -0.0355(5) 0.057(2) Uani 1 1 d .
H5A H -0.0943 0.1254 -0.0824 0.069 Uiso 1 1 calc R
C6 C 0.0713(7) 0.1767(6) -0.0489(5) 0.056(2) Uani 1 1 d .
H6A H 0.1025 0.1756 -0.1056 0.068 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.0467(4) 0.0472(3) 0.0461(4) 0.000 0.0135(3) 0.000
I2 0.0484(3) 0.0755(3) 0.0445(3) 0.0093(3) 0.0002(2) 0.0075(3)
I3 0.0795(4) 0.0980(4) 0.0499(3) 0.0042(3) -0.0084(3) 0.0046(4)
N1 0.035(4) 0.037(4) 0.022(4) 0.002(4) 0.000 0.000
N2 0.041(3) 0.058(4) 0.032(4) -0.003(3) -0.002(3) 0.001(3)
C1 0.035(3) 0.034(3) 0.033(3) 0.000(3) -0.002(3) 0.003(3)
C2 0.046(4) 0.039(4) 0.027(4) 0.001(3) -0.008(3) 0.002(3)
C3 0.047(5) 0.074(5) 0.042(5) 0.001(4) 0.000(4) -0.017(4)
C4 0.044(5) 0.084(6) 0.064(6) 0.001(5) -0.002(4) -0.023(4)
C5 0.054(5) 0.068(5) 0.050(5) -0.007(4) -0.019(4) -0.009(4)
C6 0.063(5) 0.072(5) 0.034(5) -0.006(4) -0.015(4) 0.001(4)
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
4 0 0
0 2 0
3 0 3
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
I2 I1 I2 173.86(3) . 3
I1 I2 I3 88.872(16) . .
I1 I2 I2 161.14(2) . 5_565
I3 I2 I2 76.140(18) . 5_565
I3 I3 I2 177.50(3) 3_455 .
C1 N1 C1 124.0(7) 4 .
C2 N2 C6 121.7(6) . .
N1 C1 C1 117.0(4) . 2
N1 C1 C2 113.2(5) . .
C1 C1 C2 129.6(4) 2 .
N2 C2 C3 119.1(6) . .
N2 C2 C1 120.8(6) . .
C3 C2 C1 120.1(6) . .
C4 C3 C2 119.7(6) . .
C3 C4 C5 119.7(7) . .
C6 C5 C4 118.4(7) . .
C5 C6 N2 121.4(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 I2 2.9318(5) .
I1 I2 2.9318(5) 3
I2 I3 3.4069(8) .
I2 I2 3.7502(10) 5_565
I3 I3 2.7742(11) 3_455
N1 C1 1.331(6) 4
N1 C1 1.331(6) .
N2 C2 1.320(7) .
N2 C6 1.340(7) .
C1 C1 1.441(11) 2
C1 C2 1.484(7) .
C2 C3 1.380(8) .
C3 C4 1.373(9) .
C4 C5 1.373(9) .
C5 C6 1.352(9) .
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
I2 I1 I2 I3 90.498(13) 3 .
I2 I1 I2 I2 53.52(8) 3 5_565
I1 I2 I3 I3 -15.9(3) . 3_455
I2 I2 I3 I3 152.5(3) 5_565 3_455
C1 N1 C1 C1 -9.0(5) 4 2
C1 N1 C1 C2 167.6(6) 4 .
C6 N2 C2 C3 -1.7(9) . .
C6 N2 C2 C1 178.2(6) . .
N1 C1 C2 N2 171.4(5) . .
C1 C1 C2 N2 -12.6(12) 2 .
N1 C1 C2 C3 -8.8(8) . .
C1 C1 C2 C3 167.3(8) 2 .
N2 C2 C3 C4 -0.1(10) . .
C1 C2 C3 C4 -180.0(6) . .
C2 C3 C4 C5 0.6(11) . .
C3 C4 C5 C6 0.7(12) . .
C4 C5 C6 N2 -2.5(11) . .
C2 N2 C6 C5 3.1(10) . .
