#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/31/7213149.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7213149
loop_
_publ_author_name
'Akutagawa, Tomoyuki'
'Abe, Yukako'
'Hasegawa, Tatsuo'
'Nakamura, Takayoshi'
'Inabe, Tamotsu'
'Sugiura, Ken­ich'
'Sakata, Yoshiteru'
'Christensen, Christian A.'
'Lau, Jesper'
'Becher, Jan'
_publ_section_title
;
 Crystal structures and optical properties of cation radical salts of a
 tetrathiafulvalene trisannulated macrocycle
;
_journal_issue                   11
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              2737
_journal_paper_doi               10.1039/a905362j
_journal_volume                  9
_journal_year                    1999
_chemical_formula_sum            'C39 H42 Cl3 I3 S24'
_chemical_formula_weight         1767.27
_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'
_cell_angle_alpha                104.622(10)
_cell_angle_beta                 116.501(7)
_cell_angle_gamma                81.65(1)
_cell_formula_units_Z            2
_cell_length_a                   13.653(2)
_cell_length_b                   20.303(3)
_cell_length_c                   12.677(1)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    196.2
_cell_measurement_theta_max      14.8
_cell_measurement_theta_min      12.7
_cell_volume                     3040.8(7)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    'DIRDIF92 (PATTY)'
_diffrn_measurement_device_type  'Rigaku AFC5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            14557
_diffrn_reflns_theta_max         25.5
_diffrn_standards_decay_%        1.07
_diffrn_standards_interval_count 500
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.530
_exptl_absorpt_correction_T_max  0.603
_exptl_absorpt_correction_T_min  0.442
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         2.02
_refine_diff_density_min         -1.52
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.690
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     595
_refine_ls_number_reflns         6563
_refine_ls_R_factor_obs          0.00730
_refine_ls_shift/esd_max         0.1130
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         0.0793
_reflns_number_observed          13972
_reflns_number_total             14557
_reflns_observed_criterion       >2.0sigma(I)
_cod_data_source_file            905362jsup1.cif
_cod_data_source_block           TTFtrimerI3
_cod_original_cell_volume        3040.8(6)
_cod_original_sg_symbol_H-M      'P -1         '
_cod_original_formula_sum        'C39 H42 Cl3 I3 S24 '
_cod_database_code               7213149
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
I(1) I 0.2287(1) 0.38291(6) 0.1637(1) 0.0413(3) Uani 1.00 d
I(2) I 0.3594(1) 0.50629(7) 0.2757(1) 0.0547(4) Uani 1.00 d
I(3) I 0.0941(1) 0.26568(8) 0.0589(1) 0.0558(4) Uani 1.00 d
Cl(1) Cl 0.6771(4) 0.0118(3) 0.2613(5) 0.062(2) Uani 1.00 d
Cl(2) Cl 0.8504(5) 0.1972(3) 0.4444(5) 0.066(2) Uani 1.00 d
Cl(3) Cl 1.0060(5) 0.1066(3) 0.0658(7) 0.085(2) Uani 1.00 d
S(1) S 0.8516(3) 0.1408(2) 1.7253(4) 0.031(1) Uani 1.00 d
S(2) S 0.6223(3) 0.2323(2) 1.6185(4) 0.032(1) Uani 1.00 d
S(3) S 0.4318(4) 0.3165(2) 1.4721(5) 0.049(1) Uani 1.00 d
S(4) S 0.2971(4) 0.1730(3) 1.3449(4) 0.042(1) Uani 1.00 d
S(5) S 0.4998(3) 0.1060(2) 1.5077(4) 0.030(1) Uani 1.00 d
S(6) S 0.7244(3) 0.0168(2) 1.6209(4) 0.033(1) Uani 1.00 d
S(7) S 0.9191(4) -0.0750(2) 1.6203(6) 0.065(2) Uani 1.00 d
S(8) S 1.0620(4) 0.0621(2) 1.7382(6) 0.059(2) Uani 1.00 d
S(9) S 0.3730(3) 0.4536(2) 0.7523(3) 0.0255(10) Uani 1.00 d
S(10) S 0.5869(3) 0.3729(2) 0.9076(3) 0.0251(9) Uani 1.00 d
S(11) S 0.7938(3) 0.2968(2) 1.0321(4) 0.0269(10) Uani 1.00 d
S(12) S 0.7063(3) 0.3069(2) 1.2420(4) 0.034(1) Uani 1.00 d
S(13) S 0.5112(3) 0.3895(2) 1.0942(3) 0.0244(9) Uani 1.00 d
S(14) S 0.2975(3) 0.4764(2) 0.9399(3) 0.0242(9) Uani 1.00 d
S(15) S 0.0832(3) 0.5435(2) 0.7941(4) 0.036(1) Uani 1.00 d
S(16) S 0.1644(4) 0.5131(2) 0.5801(4) 0.037(1) Uani 1.00 d
S(17) S 0.1547(3) 0.3220(2) 0.8095(3) 0.0258(9) Uani 1.00 d
S(18) S 0.3680(3) 0.2255(2) 0.9543(3) 0.0242(9) Uani 1.00 d
S(19) S 0.5061(3) 0.1012(2) 1.0384(3) 0.029(1) Uani 1.00 d
S(20) S 0.5748(3) 0.0841(2) 0.8108(3) 0.0259(10) Uani 1.00 d
S(21) S 0.4354(3) 0.2098(2) 0.7590(3) 0.0261(10) Uani 1.00 d
S(22) S 0.2254(3) 0.2989(2) 0.6154(3) 0.0253(10) Uani 1.00 d
S(23) S 0.0065(4) 0.3411(2) 0.4358(4) 0.040(1) Uani 1.00 d
S(24) S -0.0705(4) 0.3756(2) 0.6591(4) 0.039(1) Uani 1.00 d
C(1) C 1.088(1) 0.1485(9) 1.751(2) 0.048(5) Uani 1.00 d
C(2) C 0.920(1) 0.0637(8) 1.692(1) 0.030(4) Uani 1.00 d
C(3) C 0.865(1) 0.0083(8) 1.645(2) 0.038(5) Uani 1.00 d
C(4) C 0.816(2) -0.1126(9) 1.470(2) 0.057(6) Uani 1.00 d
C(5) C 0.723(1) 0.1046(7) 1.641(1) 0.023(4) Uani 1.00 d
C(6) C 0.628(1) 0.1431(7) 1.594(1) 0.022(4) Uani 1.00 d
C(7) C 0.488(1) 0.2356(8) 1.503(1) 0.032(5) Uani 1.00 d
C(8) C 0.434(1) 0.1807(8) 1.450(1) 0.032(4) Uani 1.00 d
C(9) C 0.539(2) 0.3523(7) 1.456(2) 0.037(5) Uani 1.00 d
C(10) C 0.563(1) 0.3147(7) 1.349(1) 0.027(4) Uani 1.00 d
C(11) C 0.651(1) 0.3529(8) 1.349(1) 0.032(4) Uani 1.00 d
C(12) C 0.635(1) 0.3433(6) 1.118(1) 0.019(3) Uani 1.00 d
C(13) C 0.485(1) 0.4047(6) 0.955(1) 0.022(4) Uani 1.00 d
C(14) C 0.396(1) 0.4420(6) 0.892(1) 0.022(4) Uani 1.00 d
C(15) C 0.208(1) 0.5014(7) 0.806(1) 0.024(4) Uani 1.00 d
C(16) C 0.070(1) 0.526(1) 0.918(2) 0.054(6) Uani 1.00 d
C(17) C 0.222(1) 0.4612(8) 0.484(1) 0.033(5) Uani 1.00 d
C(18) C 0.243(1) 0.4895(6) 0.718(1) 0.022(4) Uani 1.00 d
C(19) C 0.670(1) 0.3355(6) 1.031(1) 0.024(4) Uani 1.00 d
C(20) C 0.751(1) 0.2091(7) 0.946(1) 0.029(4) Uani 1.00 d
C(21) C 0.730(1) 0.1691(7) 1.020(1) 0.024(4) Uani 1.00 d
C(22) C 0.704(1) 0.0942(7) 0.954(1) 0.028(4) Uani 1.00 d
C(23) C 0.484(1) 0.1465(7) 0.847(1) 0.025(4) Uani 1.00 d
C(24) C 0.340(1) 0.2448(6) 0.817(1) 0.020(3) Uani 1.00 d
C(25) C 0.250(1) 0.2823(6) 0.754(1) 0.019(3) Uani 1.00 d
C(26) C 0.087(1) 0.3243(7) 0.579(1) 0.027(4) Uani 1.00 d
C(27) C 0.030(2) 0.264(1) 0.338(2) 0.059(6) Uani 1.00 d
C(28) C 0.054(1) 0.3362(7) 0.668(1) 0.029(4) Uani 1.00 d
C(29) C -0.107(2) 0.330(1) 0.742(2) 0.053(6) Uani 1.00 d
C(30) C 0.453(1) 0.1545(7) 0.935(1) 0.020(3) Uani 1.00 d
C(31) C 0.394(1) 0.0880(7) 1.070(1) 0.031(4) Uani 1.00 d
C(32) C 0.390(1) 0.1400(8) 1.180(1) 0.028(4) Uani 1.00 d
C(33) C 0.310(1) 0.1129(8) 1.215(1) 0.029(4) Uani 1.00 d
C(34) C 0.757(4) 0.130(2) 0.342(4) 0.23(2) Uani 1.00 d
C(35) C 0.770(3) 0.074(1) 0.366(3) 0.13(1) Uani 1.00 d
C(36) C 1.019(2) 0.022(1) 0.051(3) 0.11(1) Uani 1.00 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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)
;
S S 0.125 0.123
;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)
;
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
I(2) I(1) I(3) 177.35(6) 1_555 1_555 1_555
C(2) S(1) C(5) 92.4(7) 1_555 1_555 1_555
C(6) S(2) C(7) 93.6(7) 1_555 1_555 1_555
C(7) S(3) C(9) 103.6(7) 1_555 1_555 1_555
C(8) S(4) C(33) 101.3(7) 1_555 1_555 1_555
C(6) S(5) C(8) 93.9(7) 1_555 1_555 1_555
C(3) S(6) C(5) 92.3(7) 1_555 1_555 1_555
C(3) S(7) C(4) 101.7(9) 1_555 1_555 1_555
C(1) S(8) C(2) 103.3(8) 1_555 1_555 1_555
C(14) S(9) C(18) 95.6(7) 1_555 1_555 1_555
C(13) S(10) C(19) 96.6(7) 1_555 1_555 1_555
C(19) S(11) C(20) 101.3(7) 1_555 1_555 1_555
C(11) S(12) C(12) 103.7(7) 1_555 1_555 1_555
C(12) S(13) C(13) 97.1(6) 1_555 1_555 1_555
C(14) S(14) C(15) 95.4(7) 1_555 1_555 1_555
C(15) S(15) C(16) 102.3(7) 1_555 1_555 1_555
C(17) S(16) C(18) 103.3(7) 1_555 1_555 1_555
C(25) S(17) C(28) 94.8(7) 1_555 1_555 1_555
C(24) S(18) C(30) 93.5(6) 1_555 1_555 1_555
C(30) S(19) C(31) 105.8(7) 1_555 1_555 1_555
C(22) S(20) C(23) 103.7(7) 1_555 1_555 1_555
C(23) S(21) C(24) 93.4(6) 1_555 1_555 1_555
C(25) S(22) C(26) 93.8(7) 1_555 1_555 1_555
C(26) S(23) C(27) 102.3(8) 1_555 1_555 1_555
C(28) S(24) C(29) 102.5(8) 1_555 1_555 1_555
S(1) C(2) S(8) 119.5(9) 1_555 1_555 1_555
S(1) C(2) C(3) 118(1) 1_555 1_555 1_555
S(8) C(2) C(3) 122(1) 1_555 1_555 1_555
S(6) C(3) S(7) 116.8(10) 1_555 1_555 1_555
S(6) C(3) C(2) 116(1) 1_555 1_555 1_555
S(7) C(3) C(2) 125(1) 1_555 1_555 1_555
S(1) C(5) S(6) 114.7(7) 1_555 1_555 1_555
S(1) C(5) C(6) 122(1) 1_555 1_555 1_555
S(6) C(5) C(6) 122(1) 1_555 1_555 1_555
S(2) C(6) S(5) 114.0(7) 1_555 1_555 1_555
S(2) C(6) C(5) 124(1) 1_555 1_555 1_555
S(5) C(6) C(5) 121(1) 1_555 1_555 1_555
S(2) C(7) S(3) 117.3(10) 1_555 1_555 1_555
S(2) C(7) C(8) 119(1) 1_555 1_555 1_555
S(3) C(7) C(8) 123(1) 1_555 1_555 1_555
S(4) C(8) S(5) 115.7(10) 1_555 1_555 1_555
S(4) C(8) C(7) 127(1) 1_555 1_555 1_555
S(5) C(8) C(7) 116(1) 1_555 1_555 1_555
S(3) C(9) C(10) 115(1) 1_555 1_555 1_555
C(9) C(10) C(11) 107(1) 1_555 1_555 1_555
S(12) C(11) C(10) 112(1) 1_555 1_555 1_555
S(12) C(12) S(13) 122.3(8) 1_555 1_555 1_555
S(12) C(12) C(19) 121(1) 1_555 1_555 1_555
S(13) C(12) C(19) 116(1) 1_555 1_555 1_555
S(10) C(13) S(13) 113.7(8) 1_555 1_555 1_555
S(10) C(13) C(14) 122(1) 1_555 1_555 1_555
S(13) C(13) C(14) 123(1) 1_555 1_555 1_555
S(9) C(14) S(14) 115.5(8) 1_555 1_555 1_555
S(9) C(14) C(13) 121(1) 1_555 1_555 1_555
S(14) C(14) C(13) 123(1) 1_555 1_555 1_555
S(14) C(15) S(15) 119.8(8) 1_555 1_555 1_555
S(14) C(15) C(18) 116(1) 1_555 1_555 1_555
S(15) C(15) C(18) 123(1) 1_555 1_555 1_555
S(9) C(18) S(16) 121.1(8) 1_555 1_555 1_555
S(9) C(18) C(15) 116(1) 1_555 1_555 1_555
S(16) C(18) C(15) 122(1) 1_555 1_555 1_555
S(10) C(19) S(11) 116.1(8) 1_555 1_555 1_555
S(10) C(19) C(12) 116(1) 1_555 1_555 1_555
S(11) C(19) C(12) 127(1) 1_555 1_555 1_555
S(11) C(20) C(21) 111.4(10) 1_555 1_555 1_555
C(20) C(21) C(22) 111(1) 1_555 1_555 1_555
S(20) C(22) C(21) 113.8(10) 1_555 1_555 1_555
S(20) C(23) S(21) 114.8(7) 1_555 1_555 1_555
S(20) C(23) C(30) 128(1) 1_555 1_555 1_555
S(21) C(23) C(30) 116(1) 1_555 1_555 1_555
S(18) C(24) S(21) 114.6(8) 1_555 1_555 1_555
S(18) C(24) C(25) 124(1) 1_555 1_555 1_555
S(21) C(24) C(25) 121(1) 1_555 1_555 1_555
S(17) C(25) S(22) 114.0(7) 1_555 1_555 1_555
S(17) C(25) C(24) 123(1) 1_555 1_555 1_555
S(22) C(25) C(24) 122(1) 1_555 1_555 1_555
S(22) C(26) S(23) 117.2(9) 1_555 1_555 1_555
S(22) C(26) C(28) 117(1) 1_555 1_555 1_555
S(23) C(26) C(28) 124(1) 1_555 1_555 1_555
S(17) C(28) S(24) 118.8(9) 1_555 1_555 1_555
S(17) C(28) C(26) 115(1) 1_555 1_555 1_555
S(24) C(28) C(26) 124(1) 1_555 1_555 1_555
S(18) C(30) S(19) 120.9(7) 1_555 1_555 1_555
S(18) C(30) C(23) 117(1) 1_555 1_555 1_555
S(19) C(30) C(23) 120(1) 1_555 1_555 1_555
S(19) C(31) C(32) 112(1) 1_555 1_555 1_555
C(31) C(32) C(33) 106(1) 1_555 1_555 1_555
S(4) C(33) C(32) 110.4(10) 1_555 1_555 1_555
Cl(2) C(34) C(35) 119(2) 1_555 1_555 1_555
Cl(1) C(35) C(34) 116(3) 1_555 1_555 1_555
Cl(3) C(36) C(36) 124(3) 1_555 1_555 2_755
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I(1) I(2) 2.952(2) .
I(1) I(3) 2.881(2) .
Cl(1) C(35) 1.75(3) .
Cl(2) C(34) 1.83(3) .
Cl(3) C(36) 1.67(3) .
S(1) C(2) 1.76(1) .
S(1) C(5) 1.76(1) .
S(2) C(6) 1.75(1) .
S(2) C(7) 1.77(2) .
S(3) C(7) 1.77(1) .
S(3) C(9) 1.83(2) .
S(4) C(8) 1.75(2) .
S(4) C(33) 1.85(1) .
S(5) C(6) 1.76(1) .
S(5) C(8) 1.79(2) .
S(6) C(3) 1.79(2) .
S(6) C(5) 1.73(1) .
S(7) C(3) 1.76(2) .
S(7) C(4) 1.84(2) .
S(8) C(1) 1.79(2) .
S(8) C(2) 1.76(1) .
S(9) C(14) 1.72(1) .
S(9) C(18) 1.72(1) .
S(10) C(13) 1.74(1) .
S(10) C(19) 1.76(1) .
S(11) C(19) 1.75(1) .
S(11) C(20) 1.86(1) .
S(12) C(11) 1.83(1) .
S(12) C(12) 1.72(1) .
S(13) C(12) 1.75(1) .
S(13) C(13) 1.74(1) .
S(14) C(14) 1.71(1) .
S(14) C(15) 1.74(1) .
S(15) C(15) 1.75(1) .
S(15) C(16) 1.79(2) .
S(16) C(17) 1.78(2) .
S(16) C(18) 1.75(1) .
S(17) C(25) 1.75(1) .
S(17) C(28) 1.77(2) .
S(18) C(24) 1.75(1) .
S(18) C(30) 1.75(1) .
S(19) C(30) 1.74(1) .
S(19) C(31) 1.81(1) .
S(20) C(22) 1.87(2) .
S(20) C(23) 1.77(1) .
S(21) C(23) 1.77(1) .
S(21) C(24) 1.74(1) .
S(22) C(25) 1.75(1) .
S(22) C(26) 1.77(1) .
S(23) C(26) 1.75(2) .
S(23) C(27) 1.82(2) .
S(24) C(28) 1.74(2) .
S(24) C(29) 1.83(2) .
C(2) C(3) 1.30(2) .
C(5) C(6) 1.37(2) .
C(7) C(8) 1.29(2) .
C(9) C(10) 1.54(2) .
C(10) C(11) 1.52(2) .
C(12) C(19) 1.36(2) .
C(13) C(14) 1.36(2) .
C(15) C(18) 1.36(2) .
C(20) C(21) 1.53(2) .
C(21) C(22) 1.55(2) .
C(23) C(30) 1.33(2) .
C(24) C(25) 1.37(2) .
C(26) C(28) 1.34(2) .
C(31) C(32) 1.54(2) .
C(32) C(33) 1.55(2) .
C(34) C(35) 1.22(4) .
C(36) C(36) 1.30(5) 2_755
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
I(1) I(2) 2.952(2) .
I(1) I(3) 2.881(2) .
Cl(1) S(19) 3.493(6) 1_554
Cl(2) S(12) 3.538(6) 1_554
S(1) C(20) 3.55(2) 1_556
S(9) S(13) 3.467(5) 2_667
S(10) S(14) 3.359(5) 2_667
S(11) S(15) 3.585(6) 2_667
S(16) S(23) 3.481(5) 2_566
S(17) C(1) 3.58(2) 1_454
C(1) C(4) 3.49(3) 2_758
C(13) C(14) 3.42(2) 2_667
C(14) C(14) 3.59(3) 2_667
