#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/38/4503884.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_4503884
loop_
_publ_author_name
'Yamamoto, Hiroshi M.'
'Kosaka, Yosuke'
'Maeda, Ryoko'
'Yamaura, Jun-ichi'
'Nakao, Akiko'
'Nakamura, Toshikazu'
'Kato, Reizo'
_publ_section_title
;
 Supramolecular insulating networks sheathing conducting nanowires based
 on organic radical cations.
;
_journal_issue                   1
_journal_name_full               'ACS nano'
_journal_page_first              143
_journal_page_last               155
_journal_paper_doi               10.1021/nn700035t
_journal_volume                  2
_journal_year                    2008
_chemical_formula_moiety         '2(C6 H6 Se2), 3(C I2), Cl '
_chemical_formula_sum            'C15 H12 Cl I6 Se4'
_chemical_formula_weight         1304.98
_space_group_IT_number           55
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      55
_symmetry_space_group_name_Hall  '-P 2 2ab'
_symmetry_space_group_name_H-M   'P b a m'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.322(1)
_cell_length_b                   22.811(2)
_cell_length_c                   7.9230(7)
_cell_measurement_temperature    293
_cell_volume                     2588.4(4)
_computing_data_reduction        'teXsan Ver. 2.0'
_computing_publication_material  'teXsan Ver. 2.0'
_computing_structure_refinement  'teXsan Ver. 2.0'
_computing_structure_solution    SHELXS97
_diffrn_measured_fraction_theta_full 1.0038
_diffrn_measured_fraction_theta_max 1.0038
_diffrn_measurement_device_type  'RIGAKU AFC6S'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6568
_diffrn_reflns_theta_full        34.99
_diffrn_reflns_theta_max         34.99
_exptl_absorpt_coefficient_mu    12.94
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    3.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2292.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         3.80
_refine_diff_density_min         -4.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.468
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     0
_refine_ls_number_reflns         2130
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1580
_reflns_number_gt                2130
_reflns_number_total             6251
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            nn700035t-file024.cif
_cod_data_source_block           (HMTSF)2Cl.TIE
_cod_original_sg_symbol_H-M      'P b a m      '
_cod_original_formula_sum        'C15 H12 Cl I6 Se4 '
_cod_database_code               4503884
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,z
1/2+x,1/2-y,-z
1/2-x,1/2+y,-z
-x,-y,-z
x,y,-z
1/2-x,1/2+y,z
1/2+x,1/2-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I(1) I -0.06603(6) 0.43460(3) 0.2307(1) 0.05(2) Uani 1.00 1 d .
I(2) I -0.00763(5) 0.26341(3) 0.2315(1) 0.0434(2) Uani 1.00 1 d .
I(3) I 0.20731(5) 0.18958(3) 0.2320(1) 0.0476(2) Uani 1.00 1 d .
Se(1) Se -0.0164(1) 0.09478(9) 0.1822(4) 0.04(4) Uani 0.50 2 d P
Se(2) Se -0.1477(2) -0.01766(9) 0.1811(4) 0.0418(5) Uani 0.50 2 d P
Se(3) Se 0.0275(2) -0.0989(1) 0.3438(4) 0.0409(5) Uani 0.50 2 d P
Se(4) Se 0.1599(2) 0.0137(1) 0.3438(4) 0.04(4) Uani 0.50 2 d P
Cl(1) Cl 0.3624(3) 0.1598(2) 0.5000 0.0446(9) Uani 1.00 2 d S
C(1) C 0.0000 0.5000 0.076(3) 0.052(4) Uani 1.00 2 d S
C(2) C 0.0975(8) 0.2239(5) 0.078(2) 0.0(2) Uani 1.00 1 d .
C(3) C -0.027(2) 0.0136(8) 0.25(1) 0.09(2) Uani 0.50 2 d P
C(4) C -0.136(1) 0.1013(7) 0.110(3) 0.030(4) Uani 0.50 2 d P
C(5) C -0.195(1) 0.0551(8) 0.101(3) 0.0(4) Uani 0.50 2 d P
C(6) C -0.285(1) 0.066(1) 0.0000 0.09(1) Uani 1.00 2 d S
C(7) C -0.283(1) 0.1351(7) 0.0000 0.039(3) Uani 1.00 2 d S
C(8) C -0.182(1) 0.1567(9) 0.0000 0.1(7) Uani 1.00 2 d S
C(9) C 0.042(1) -0.0189(7) 0.266(10) 0.05(1) Uani 0.50 2 d P
C(10) C 0.210(2) -0.062(1) 0.412(3) 0.045(6) Uani 0.50 2 d P
C(11) C 0.155(1) -0.107(1) 0.402(3) 0.0(5) Uani 0.50 2 d P
C(12) C 0.202(1) -0.1618(8) 0.5000 0.077(8) Uani 1.00 2 d S
C(13) C 0.298(2) -0.1387(10) 0.5000 0.061(5) Uani 1.00 2 d S
C(14) C 0.305(1) -0.0726(8) 0.5000 0.1(6) Uani 1.00 2 d S
H(1) H -0.2822 0.0498 -0.1108 0.1099 Uiso 1.00 1 calc .
H(2) H -0.3389 0.0505 0.0560 0.1099 Uiso 1.00 1 calc .
H(3) H -0.3144 0.1493 -0.0979 0.0471 Uiso 1.00 1 calc .
H(4) H -0.3144 0.1493 0.0979 0.0471 Uiso 1.00 1 calc .
H(5) H -0.1746 0.1933 0.0559 0.0934 Uiso 1.00 1 calc .
H(6) H -0.1564 0.1594 -0.1106 0.0934 Uiso 1.00 1 calc .
H(7) H 0.1780 -0.1669 0.6106 0.0929 Uiso 1.00 1 calc .
H(8) H 0.1966 -0.1975 0.4390 0.0929 Uiso 1.00 1 calc .
H(9) H 0.3293 -0.1529 0.5979 0.0727 Uiso 1.00 1 calc .
H(10) H 0.3293 -0.1528 0.4021 0.0727 Uiso 1.00 1 calc .
H(11) H 0.3560 -0.0584 0.4362 0.0889 Uiso 1.00 1 calc .
H(12) H 0.3069 -0.0566 0.6107 0.0889 Uiso 1.00 1 calc .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Se Se -0.093 2.226
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
I I -0.474 1.812
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
Cl Cl 0.148 0.159
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
C C 0.003 0.002
;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)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(3) Se(1) C(4) 95(1) yes
C(3) Se(2) C(5) 95(1) yes
C(9) Se(3) C(11) 93(1) yes
C(9) Se(4) C(10) 94(1) yes
I(2) C(2) I(3) 110.3(6) yes
Se(1) C(3) Se(2) 109(2) yes
Se(1) C(3) C(9) 122(2) yes
Se(2) C(3) C(9) 120(2) yes
Se(1) C(4) C(5) 122(1) yes
Se(1) C(4) C(8) 126(1) yes
C(5) C(4) C(8) 108(1) yes
Se(2) C(5) C(4) 116(1) yes
Se(2) C(5) C(6) 127(1) yes
C(4) C(5) C(6) 115(1) yes
C(5) C(6) C(7) 98(1) yes
C(5) C(6) H(1) 112.2 no
C(5) C(6) H(2) 112.2 no
C(7) C(6) H(1) 112.2 no
C(7) C(6) H(2) 112.2 no
H(1) C(6) H(2) 109.5 no
C(6) C(7) C(8) 109(1) yes
C(6) C(7) H(3) 109.4 no
C(6) C(7) H(4) 109.4 no
C(8) C(7) H(3) 109.4 no
C(8) C(7) H(4) 109.4 no
H(3) C(7) H(4) 109.5 no
C(4) C(8) C(7) 97(1) yes
C(4) C(8) H(5) 112.4 no
C(4) C(8) H(6) 112.4 no
C(7) C(8) H(5) 112.4 no
C(7) C(8) H(6) 112.4 no
H(5) C(8) H(6) 109.5 no
Se(3) C(9) Se(4) 110(2) yes
Se(3) C(9) C(3) 120(2) yes
Se(4) C(9) C(3) 119(2) yes
Se(4) C(10) C(11) 117(1) yes
Se(4) C(10) C(14) 126(1) yes
C(11) C(10) C(14) 115(2) yes
Se(3) C(11) C(10) 121(1) yes
Se(3) C(11) C(12) 126(1) yes
C(10) C(11) C(12) 109(1) yes
C(11) C(12) C(13) 96(1) yes
C(11) C(12) H(7) 112.7 no
C(11) C(12) H(8) 112.7 no
C(13) C(12) H(7) 112.7 no
C(13) C(12) H(8) 112.7 no
H(7) C(12) H(8) 109.5 no
C(12) C(13) C(14) 114(1) yes
C(12) C(13) H(9) 108.2 no
C(12) C(13) H(10) 108.2 no
C(14) C(13) H(9) 108.3 no
C(14) C(13) H(10) 108.3 no
H(9) C(13) H(10) 109.5 no
C(10) C(14) C(13) 96(1) yes
C(10) C(14) H(11) 112.6 no
C(10) C(14) H(12) 112.6 no
C(13) C(14) H(11) 112.6 no
C(13) C(14) H(12) 112.6 no
H(11) C(14) H(12) 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I(1) C(1) 2.15(1) . yes
I(2) C(2) 2.14(1) . yes
I(3) C(2) 2.14(1) . yes
Se(1) Se(3) 1.293(4) 2_555 no
Se(1) C(3) 1.94(3) . yes
Se(1) C(4) 1.82(2) . yes
Se(1) C(9) 1.89(3) 2_555 no
Se(2) Se(4) 1.304(4) 2_555 no
Se(2) C(3) 1.95(4) . yes
Se(2) C(5) 1.90(2) . yes
Se(2) C(9) 1.85(3) 2_555 no
Se(3) Se(3) 2.476(6) 6_556 no
Se(3) C(3) 2.08(4) 2_555 no
Se(3) C(9) 1.94(3) . yes
Se(3) C(11) 1.90(2) . yes
Se(4) Se(4) 2.475(6) 6_556 no
Se(4) C(3) 2.13(4) 2_555 no
Se(4) C(9) 1.95(3) . yes
Se(4) C(10) 1.94(3) . yes
C(1) C(1) 1.20(4) 5_565 no
C(2) C(2) 1.23(3) 6_555 no
C(3) C(3) 0.99(4) 2_555 no
C(3) C(9) 1.24(3) . yes
C(3) C(9) 0.27(6) 2_555 no
C(4) C(4) 1.74(4) 6_555 no
C(4) C(5) 1.35(2) . yes
C(4) C(8) 1.67(3) . yes
C(5) C(5) 1.60(5) 6_555 no
C(5) C(6) 1.54(2) . yes
C(5) H(1) 1.256 6_555 no
C(6) C(7) 1.59(3) . yes
C(6) H(1) 0.950 . no
C(6) H(1) 0.950 6_555 no
C(6) H(2) 0.950 . no
C(6) H(2) 0.950 6_555 no
C(7) C(8) 1.54(3) . yes
C(7) H(3) 0.950 . no
C(7) H(4) 0.950 . no
C(8) H(5) 0.950 . no
C(8) H(5) 0.950 6_555 no
C(8) H(6) 0.950 . no
C(8) H(6) 0.950 6_555 no
C(9) C(9) 1.48(4) 2_555 no
C(10) C(10) 1.39(5) 6_556 no
C(10) C(11) 1.30(4) . yes
C(10) C(14) 1.54(3) . yes
C(11) C(11) 1.55(5) 6_556 no
C(11) C(12) 1.62(3) . yes
C(12) C(13) 1.48(3) . yes
C(12) H(7) 0.950 . no
C(12) H(7) 0.950 6_556 no
C(12) H(8) 0.950 . no
C(12) H(8) 0.950 6_556 no
C(13) C(14) 1.51(3) . yes
C(13) H(9) 0.950 . no
C(13) H(10) 0.950 . no
C(14) H(11) 0.950 . no
C(14) H(11) 0.950 6_556 no
C(14) H(12) 0.950 . no
C(14) H(12) 0.950 6_556 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
I(1) Cl(1) 3.200(4) 3_456
I(1) I(1) 3.533(2) 2_565
I(2) Cl(1) 3.326(4) 3_456
C(1) C(6) 3.47(2) 3_555
C(1) C(6) 3.47(2) 4_455
C(6) C(10) 3.44(3) 5_555
C(8) C(11) 3.41(3) 5_555
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_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I(1) C(1) C(1) I(1) 0.0 5_565 6_555 yes
I(1) C(1) C(1) I(1) 180.0 5_565 5_565 yes
I(2) C(2) C(2) I(2) 0.0 6_555 6_555 yes
I(2) C(2) C(2) I(3) 175.6(8) 6_555 6_555 yes
I(3) C(2) C(2) I(3) 0.0 6_555 6_555 yes
Se(1) C(3) Se(2) C(5) -6(4) . . yes
Se(1) C(3) C(9) Se(3) 177(4) . . yes
Se(1) C(3) C(9) Se(4) 34(10) . . yes
Se(1) C(4) C(5) Se(2) 3(2) . . yes
Se(1) C(4) C(5) C(6) -166(1) . . yes
Se(1) C(4) C(8) C(7) -175(1) . . yes
Se(2) C(3) Se(1) C(4) 7(4) . . yes
Se(2) C(3) C(9) Se(3) -34(10) . . yes
Se(2) C(3) C(9) Se(4) -178(4) . . yes
Se(2) C(5) C(4) C(8) 168(1) . . yes
Se(2) C(5) C(6) C(7) 173(1) . . yes
Se(3) C(11) C(10) Se(4) -5(3) . . yes
Se(3) C(11) C(10) C(14) 166(1) . . yes
Se(3) C(11) C(12) C(13) 179(1) . . yes
Se(4) C(9) Se(3) C(11) -15(2) . . yes
Se(4) C(10) C(11) C(12) -168(1) . . yes
Se(4) C(10) C(14) C(13) -175(1) . . yes
C(3) Se(1) C(4) C(5) -7(3) . . yes
C(3) Se(1) C(4) C(8) -169(3) . . yes
C(3) Se(2) C(5) C(4) 2(3) . . yes
C(3) Se(2) C(5) C(6) 170(3) . . yes
C(3) C(9) Se(3) C(11) -161(7) . . yes
C(3) C(9) Se(4) C(10) 159(7) . . yes
C(4) Se(1) C(3) C(9) 157(8) . . yes
C(4) C(5) C(6) C(7) -17(1) . . yes
C(4) C(8) C(7) C(6) -31.8(8) . . yes
C(5) Se(2) C(3) C(9) -157(7) . . yes
C(5) C(4) C(8) C(7) 20(1) . . yes
C(5) C(6) C(7) C(8) 31.6(9) . . yes
C(6) C(5) C(4) C(8) -1(2) . . yes
C(9) Se(3) C(11) C(10) 13(3) . . yes
C(9) Se(3) C(11) C(12) 172(2) . . yes
C(9) Se(4) C(10) C(11) -5(2) . . yes
C(9) Se(4) C(10) C(14) -176(2) . . yes
C(10) C(11) C(12) C(13) -18(2) . . yes
C(10) C(14) C(13) C(12) -27(1) . . yes
C(11) C(10) C(14) C(13) 12(2) . . yes
C(11) C(12) C(13) C(14) 28(1) . . yes
C(12) C(11) C(10) C(14) 3(2) . . yes
