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#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/45/7204593.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_7204593
loop_
_publ_author_name
'Mukai, Kazuo'
'Jinno, Syunsuke'
'Shimobe, Yasuo'
'Azuma, Nagao'
'Taniguchi, Masateru'
'Misaki, Yohji'
'Tanaka, Kazuyoshi'
'Inoue, Katsuya'
'Hosokoshi, Yuko'
_publ_section_title
;
 Genuine organic magnetic semiconductors: electrical and magnetic
 properties of the TCNQ and iodide salts of
 methylpyridinium-substituted verdazyl radicals
;
_journal_issue                   7
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              1614
_journal_paper_doi               10.1039/b300029j
_journal_volume                  13
_journal_year                    2003
_chemical_formula_sum            'C20 H19 I N5'
_chemical_formula_weight         456.31
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             'Tue Apr  2 16:51:59 2002'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                96.493(9)
_cell_angle_beta                 91.11(1)
_cell_angle_gamma                76.89(1)
_cell_formula_units_Z            2
_cell_length_a                   8.703(2)
_cell_length_b                   13.522(1)
_cell_length_c                   8.3084(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298.2
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      25.50
_cell_volume                     946.1(2)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 1.0760
_diffrn_measured_fraction_theta_max 1.0760
_diffrn_measurement_device_type  'Rigaku AFC5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3166
_diffrn_reflns_theta_full        61.61
_diffrn_reflns_theta_max         61.61
_diffrn_standards_decay_%        1.12
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    13.526
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.486
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews,1968)'
_exptl_crystal_colour            dark-violet
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         1.21
_refine_diff_density_min         -1.03
_refine_ls_extinction_coef       0.17(1)
_refine_ls_extinction_method     'Zachariasen(1967) type 2 Gaussian isotropic'
_refine_ls_goodness_of_fit_ref   1.383
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3156
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w =3D 1/[σ²(Fo²) + (0.07400(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                2944
_reflns_number_total             3166
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            b300029j.txt
_cod_data_source_block           '[p-MePyDV]I_99-10-20_Cu-ta'
_cod_original_cell_volume        946.2(2)
_cod_original_formula_sum        'C20 H19 I N5 '
_cod_database_code               7204593
loop_
_symmetry_equiv_pos_as_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 0.25399(4) 0.46592(2) 0.20640(4) 0.0637(1) Uani 1.00 d . . .
N(1) N 0.5580(4) 0.0836(3) 0.1957(5) 0.0412(9) Uani 1.00 d . . .
N(2) N 0.6081(4) -0.0180(2) 0.2011(4) 0.0383(9) Uani 1.00 d . . .
N(3) N 0.3722(4) -0.0151(2) 0.3479(4) 0.0372(9) Uani 1.00 d . . .
N(4) N 0.3276(4) 0.0859(2) 0.3369(4) 0.0359(8) Uani 1.00 d . . .
N(5) N 0.6619(5) -0.3790(3) 0.2917(5) 0.047(1) Uani 1.00 d . . .
C(1) C 0.5070(4) -0.0611(3) 0.2701(5) 0.0335(10) Uani 1.00 d . . .
C(2) C 0.3893(5) 0.1257(4) 0.2043(6) 0.048(1) Uani 1.00 d . . .
C(3) C 0.6654(5) 0.1360(3) 0.1408(5) 0.038(1) Uani 1.00 d . . .
C(4) C 0.8248(6) 0.0912(4) 0.1370(6) 0.050(1) Uani 1.00 d . . .
C(5) C 0.9305(6) 0.1433(5) 0.0856(7) 0.060(2) Uani 1.00 d . . .
C(6) C 0.8788(7) 0.2392(4) 0.0352(7) 0.062(2) Uani 1.00 d . . .
C(7) C 0.7205(7) 0.2829(4) 0.0372(6) 0.054(1) Uani 1.00 d . . .
C(8) C 0.6129(6) 0.2333(3) 0.0920(6) 0.046(1) Uani 1.00 d . . .
C(9) C 0.5597(5) -0.1724(3) 0.2779(5) 0.037(1) Uani 1.00 d . . .
C(10) C 0.4758(5) -0.2244(3) 0.3654(6) 0.047(1) Uani 1.00 d . . .
C(11) C 0.5279(6) -0.3270(4) 0.3702(7) 0.053(1) Uani 1.00 d . . .
C(12) C 0.7454(5) -0.3307(3) 0.2093(5) 0.042(1) Uani 1.00 d . . .
C(13) C 0.6970(5) -0.2277(3) 0.1994(5) 0.040(1) Uani 1.00 d . . .
C(14) C 0.7137(8) -0.4898(4) 0.2994(8) 0.068(2) Uani 1.00 d . . .
C(15) C 0.1909(4) 0.1409(3) 0.4234(5) 0.0329(9) Uani 1.00 d . . .
C(16) C 0.1354(5) 0.2450(3) 0.4095(5) 0.041(1) Uani 1.00 d . . .
C(17) C 0.0046(5) 0.2991(3) 0.5009(6) 0.048(1) Uani 1.00 d . . .
C(18) C -0.0711(5) 0.2511(4) 0.6015(6) 0.049(1) Uani 1.00 d . . .
C(19) C -0.0170(5) 0.1481(4) 0.6118(6) 0.047(1) Uani 1.00 d . . .
C(20) C 0.1141(5) 0.0928(3) 0.5230(5) 0.039(1) Uani 1.00 d . . .
H(1) H 0.3687 0.1981 0.2228 0.0581 Uiso 1.00 calc=20 . . .
H(2) H 0.3414 0.1059 0.1058 0.0581 Uiso 1.00 calc=20 . . .
H(3) H 0.8613 0.0248 0.1697 0.0597 Uiso 1.00 calc=20 . . .
H(4) H 1.0402 0.1128 0.0848 0.0721 Uiso 1.00 calc=20 . . .
H(5) H 0.9523 0.2745 -0.0004 0.0741 Uiso 1.00 calc=20 . . .
H(6) H 0.6843 0.3482 0.0005 0.0647 Uiso 1.00 calc=20 . . .
H(7) H 0.5038 0.2652 0.0964 0.0550 Uiso 1.00 calc=20 . . .
H(8) H 0.3823 -0.1885 0.4220 0.0559 Uiso 1.00 calc=20 . . .
H(9) H 0.4694 -0.3624 0.4292 0.0639 Uiso 1.00 calc=20 . . .
H(10) H 0.8401 -0.3680 0.1563 0.0509 Uiso 1.00 calc=20 . . .
H(11) H 0.7574 -0.1943 0.1389 0.0482 Uiso 1.00 calc=20 . . .
H(12) H 0.8072 -0.5158 0.2367 0.0811 Uiso 1.00 calc=20 . . .
H(13) H 0.6333 -0.5225 0.2576 0.0811 Uiso 1.00 calc=20 . . .
H(14) H 0.7341 -0.5026 0.4087 0.0811 Uiso 1.00 calc=20 . . .
H(15) H 0.1862 0.2783 0.3388 0.0498 Uiso 1.00 calc=20 . . .
H(16) H -0.0330 0.3701 0.4937 0.0575 Uiso 1.00 calc=20 . . .
H(17) H -0.1601 0.2887 0.6635 0.0593 Uiso 1.00 calc=20 . . .
H(18) H -0.0698 0.1146 0.6802 0.0563 Uiso 1.00 calc=20 . . .
H(19) H 0.1507 0.0217 0.5309 0.0465 Uiso 1.00 calc=20 . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
I I -0.326 6.836
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N(2) N(1) C(2) 117.3(3) . . . yes
N(2) N(1) C(3) 117.6(3) . . . yes
C(2) N(1) C(3) 122.9(3) . . . yes
N(1) N(2) C(1) 114.6(3) . . . yes
N(4) N(3) C(1) 114.1(3) . . . yes
N(3) N(4) C(2) 118.1(3) . . . yes
N(3) N(4) C(15) 117.5(3) . . . yes
C(2) N(4) C(15) 121.6(3) . . . yes
C(11) N(5) C(12) 120.4(4) . . . yes
C(11) N(5) C(14) 119.1(4) . . . yes
C(12) N(5) C(14) 120.5(4) . . . yes
N(2) C(1) N(3) 128.1(4) . . . yes
N(2) C(1) C(9) 115.5(3) . . . yes
N(3) C(1) C(9) 115.9(4) . . . yes
N(1) C(2) N(4) 107.7(3) . . . yes
N(1) C(3) C(4) 119.6(4) . . . yes
N(1) C(3) C(8) 120.7(4) . . . yes
C(4) C(3) C(8) 119.7(4) . . . yes
C(3) C(4) C(5) 119.7(4) . . . yes
C(4) C(5) C(6) 120.8(5) . . . yes
C(5) C(6) C(7) 119.3(4) . . . yes
C(6) C(7) C(8) 120.8(5) . . . yes
C(3) C(8) C(7) 119.6(4) . . . yes
C(1) C(9) C(10) 121.4(4) . . . yes
C(1) C(9) C(13) 120.6(4) . . . yes
C(10) C(9) C(13) 118.0(4) . . . yes
C(9) C(10) C(11) 119.9(4) . . . yes
N(5) C(11) C(10) 120.8(4) . . . yes
N(5) C(12) C(13) 121.0(4) . . . yes
C(9) C(13) C(12) 119.9(4) . . . yes
N(4) C(15) C(16) 119.6(4) . . . yes
N(4) C(15) C(20) 120.2(4) . . . yes
C(16) C(15) C(20) 120.1(4) . . . yes
C(15) C(16) C(17) 118.9(4) . . . yes
C(16) C(17) C(18) 120.9(4) . . . yes
C(17) C(18) C(19) 119.6(4) . . . yes
C(18) C(19) C(20) 120.6(4) . . . yes
C(15) C(20) C(19) 119.9(4) . . . yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N(1) N(2) 1.349(5) . . yes
N(1) C(2) 1.450(6) . . yes
N(1) C(3) 1.405(5) . . yes
N(2) C(1) 1.330(5) . . yes
N(3) N(4) 1.345(5) . . yes
N(3) C(1) 1.337(5) . . yes
N(4) C(2) 1.442(6) . . yes
N(4) C(15) 1.413(5) . . yes
N(5) C(11) 1.354(6) . . yes
N(5) C(12) 1.327(6) . . yes
N(5) C(14) 1.472(6) . . yes
C(1) C(9) 1.479(6) . . yes
C(3) C(4) 1.381(7) . . yes
C(3) C(8) 1.394(6) . . yes
C(4) C(5) 1.380(7) . . yes
C(5) C(6) 1.383(8) . . yes
C(6) C(7) 1.370(8) . . yes
C(7) C(8) 1.380(7) . . yes
C(9) C(10) 1.387(6) . . yes
C(9) C(13) 1.388(6) . . yes
C(10) C(11) 1.363(6) . . yes
C(12) C(13) 1.372(6) . . yes
C(15) C(16) 1.398(6) . . yes
C(15) C(20) 1.377(6) . . yes
C(16) C(17) 1.393(6) . . yes
C(17) C(18) 1.375(7) . . yes
C(18) C(19) 1.377(7) . . yes
C(19) C(20) 1.388(6) . . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N(2) C(20) 3.365(5) . 2_656 ?
N(2) C(2) 3.513(6) . 2_655 ?
N(3) N(3) 3.387(7) . 2_656 ?
N(3) C(1) 3.444(5) . 2_656 ?
N(4) C(9) 3.482(5) . 2_656 ?
N(4) C(1) 3.562(5) . 2_656 ?
N(4) C(10) 3.576(6) . 2_656 ?
N(5) C(16) 3.580(6) . 2_656 ?
C(5) C(16) 3.522(7) . 1_655 ?
C(5) C(15) 3.571(7) . 1_655 ?
C(7) C(14) 3.550(7) . 1_565 ?
C(8) C(9) 3.492(6) . 2_655 ?
C(8) C(13) 3.598(6) . 2_655 ?
C(9) C(15) 3.320(5) . 2_656 ?
C(9) C(20) 3.572(5) . 2_656 ?
C(12) C(17) 3.271(6) . 2_656 ?
C(12) C(16) 3.470(6) . 2_656 ?
C(12) C(18) 3.535(6) . 2_656 ?
C(13) C(20) 3.408(6) . 2_656 ?
C(13) C(15) 3.423(6) . 2_656 ?
C(13) C(19) 3.491(6) . 2_656 ?
C(13) C(16) 3.546(6) . 2_656 ?
C(13) C(18) 3.589(6) . 2_656 ?
C(20) C(20) 3.520(8) . 2_556 ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N(1) N(2) C(1) N(3) -7.4(6) . . . . yes
N(1) N(2) C(1) C(9) -179.8(3) . . . . yes
N(1) C(2) N(4) N(3) -47.5(5) . . . . yes
N(1) C(2) N(4) C(15) 151.8(3) . . . . yes
N(1) C(3) C(4) C(5) -178.9(4) . . . . yes
N(1) C(3) C(8) C(7) -179.5(4) . . . . yes
N(2) N(1) C(2) N(4) 47.9(5) . . . . yes
N(2) N(1) C(3) C(4) -17.6(6) . . . . yes
N(2) N(1) C(3) C(8) 163.2(4) . . . . yes
N(2) C(1) N(3) N(4) 8.2(6) . . . . yes
N(2) C(1) C(9) C(10) 171.3(4) . . . . yes
N(2) C(1) C(9) C(13) -7.6(5) . . . . yes
N(3) N(4) C(15) C(16) -176.8(4) . . . . yes
N(3) N(4) C(15) C(20) 4.2(5) . . . . yes
N(3) C(1) C(9) C(10) -2.0(6) . . . . yes
N(3) C(1) C(9) C(13) 179.1(4) . . . . yes
N(4) N(3) C(1) C(9) -179.5(3) . . . . yes
N(4) C(2) N(1) C(3) -149.3(4) . . . . yes
N(4) C(15) C(16) C(17) -177.3(4) . . . . yes
N(4) C(15) C(20) C(19) 177.8(4) . . . . yes
N(5) C(11) C(10) C(9) 0.7(7) . . . . yes
N(5) C(12) C(13) C(9) 0.7(6) . . . . yes
C(1) N(2) N(1) C(2) -23.0(5) . . . . yes
C(1) N(2) N(1) C(3) 173.2(4) . . . . yes
C(1) N(3) N(4) C(2) 21.9(5) . . . . yes
C(1) N(3) N(4) C(15) -176.6(3) . . . . yes
C(1) C(9) C(10) C(11) -179.9(4) . . . . yes
C(1) C(9) C(13) C(12) 179.2(4) . . . . yes
C(2) N(1) C(3) C(4) 179.6(4) . . . . yes
C(2) N(1) C(3) C(8) 0.4(6) . . . . yes
C(2) N(4) C(15) C(16) -16.0(6) . . . . yes
C(2) N(4) C(15) C(20) 165.1(4) . . . . yes
C(3) C(4) C(5) C(6) -1.0(8) . . . . yes
C(3) C(8) C(7) C(6) -2.2(7) . . . . yes
C(4) C(3) C(8) C(7) 1.3(7) . . . . yes
C(4) C(5) C(6) C(7) 0.2(8) . . . . yes
C(5) C(4) C(3) C(8) 0.2(7) . . . . yes
C(5) C(6) C(7) C(8) 1.4(8) . . . . yes
C(10) C(9) C(13) C(12) 0.3(6) . . . . yes
C(10) C(11) N(5) C(12) 0.3(7) . . . . yes
C(10) C(11) N(5) C(14) -179.8(5) . . . . yes
C(11) N(5) C(12) C(13) -1.0(6) . . . . yes
C(11) C(10) C(9) C(13) -1.0(7) . . . . yes
C(13) C(12) N(5) C(14) 179.0(4) . . . . yes
C(15) C(16) C(17) C(18) -1.1(7) . . . . yes
C(15) C(20) C(19) C(18) -0.1(7) . . . . yes
C(16) C(15) C(20) C(19) -1.1(6) . . . . yes
C(16) C(17) C(18) C(19) -0.1(7) . . . . yes
C(17) C(16) C(15) C(20) 1.7(6) . . . . yes
C(17) C(18) C(19) C(20) 0.7(7) . . . . yes
C(17) C(18) C(19) C(20) 0.7(7) . . . . yes
