#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:51:47 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179543 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/12/4501229.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_4501229
loop_
_publ_author_name
'Shin, Kyung-Soon'
'Brezgunova, Mariya'
'Jeannin, Olivier'
'Roisnel, Thierry'
'Camerel, Franck'
'Auban-Senzier, Pascale'
'Fourmigué, Marc'
_publ_section_title
;
 Strong Iodine···Oxygen Interactions in Molecular
 Conductors Incorporating Sulfonate Anions
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5337
_journal_paper_doi               10.1021/cg200934r
_journal_volume                  11
_journal_year                    2011
_chemical_formula_moiety         'C10 H6 O6 S2, 2(C8 H4 I2 S6)'
_chemical_formula_sum            'C26 H14 I4 O6 S14'
_chemical_formula_weight         1378.95
_chemical_name_common            '(EDT-TTFI2)2,2,6-naphtalene bis(sulfonate)'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.320(3)
_cell_angle_beta                 96.260(3)
_cell_angle_gamma                99.933(3)
_cell_formula_units_Z            1
_cell_length_a                   7.9840(7)
_cell_length_b                   10.7355(9)
_cell_length_c                   11.4398(10)
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.38
_cell_volume                     936.62(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15421
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    4.150
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             654
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.472
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0189
_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)+(0.0049P)²+1.7043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0421
_refine_ls_wR_factor_ref         0.0458
_reflns_number_gt                3898
_reflns_number_total             4209
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200934r_si_001.cif
_cod_data_source_block           2,6napht
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4501229
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
I1 I 0.39807(2) -0.250724(16) -0.388547(15) 0.01490(5) Uani 1 1 d .
I2 I 0.39093(2) -0.447971(16) -0.145264(15) 0.01539(5) Uani 1 1 d .
S1 S 0.29223(9) -0.03921(6) -0.17808(6) 0.01580(13) Uani 1 1 d .
S2 S 0.28989(9) -0.18713(6) 0.01116(6) 0.01596(14) Uani 1 1 d .
S3 S 0.18484(9) 0.05240(6) 0.19056(6) 0.01530(13) Uani 1 1 d .
S4 S 0.10276(9) 0.25990(7) 0.37251(6) 0.01817(14) Uani 1 1 d .
S5 S 0.11167(10) 0.43341(7) 0.14222(7) 0.02168(15) Uani 1 1 d .
S6 S 0.19360(9) 0.19932(6) 0.00008(6) 0.01670(14) Uani 1 1 d .
C1 C 0.2562(3) -0.0471(3) -0.0332(2) 0.0146(5) Uani 1 1 d .
C2 C 0.3386(3) -0.1932(2) -0.2151(2) 0.0144(5) Uani 1 1 d .
C3 C 0.3369(3) -0.2620(2) -0.1273(2) 0.0153(5) Uani 1 1 d .
C4 C 0.2118(3) 0.0554(3) 0.0434(2) 0.0144(5) Uani 1 1 d .
C5 C 0.1407(3) 0.2075(2) 0.2255(2) 0.0141(5) Uani 1 1 d .
C6 C 0.1868(4) 0.4312(3) 0.3884(3) 0.0217(6) Uani 1 1 d .
H6A H 0.1824 0.4765 0.4698 0.026 Uiso 1 1 calc R
H6B H 0.3063 0.4433 0.3761 0.026 Uiso 1 1 calc R
C7 C 0.0876(4) 0.4904(3) 0.2997(3) 0.0236(6) Uani 1 1 d .
H7A H 0.1256 0.5838 0.3215 0.028 Uiso 1 1 calc R
H7B H -0.0334 0.4711 0.3074 0.028 Uiso 1 1 calc R
C8 C 0.1444(3) 0.2763(3) 0.1375(2) 0.0152(5) Uani 1 1 d .
S1A S 0.47388(8) 0.23792(6) -0.30743(6) 0.01269(13) Uani 1 1 d .
O1A O 0.4557(2) 0.30204(17) -0.18557(16) 0.0154(4) Uani 1 1 d .
O2A O 0.5243(3) 0.33103(19) -0.38164(17) 0.0209(4) Uani 1 1 d .
O3A O 0.5801(2) 0.14063(19) -0.30967(18) 0.0210(4) Uani 1 1 d .
C1A C -0.0452(3) 0.1375(2) -0.3871(2) 0.0142(5) Uani 1 1 d .
H1A H -0.1390 0.1693 -0.3608 0.017 Uiso 1 1 calc R
C2A C 0.1190(3) 0.2009(2) -0.3357(2) 0.0150(5) Uani 1 1 d .
H2A H 0.1359 0.2754 -0.2749 0.018 Uiso 1 1 calc R
C3A C 0.2623(3) 0.1527(2) -0.3756(2) 0.0124(5) Uani 1 1 d .
C4A C 0.2410(3) 0.0440(2) -0.4656(2) 0.0130(5) Uani 1 1 d .
H4A H 0.3365 0.0142 -0.4911 0.016 Uiso 1 1 calc R
C5A C 0.0722(3) -0.0236(2) -0.5201(2) 0.0125(5) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_
_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
C1 S1 C2 95.65(13) . .
C1 S2 C3 95.30(13) . .
C4 S3 C5 95.36(13) . .
C5 S4 C6 97.69(13) . .
C8 S5 C7 102.90(13) . .
C4 S6 C8 95.44(13) . .
C4 C1 S1 121.6(2) . .
C4 C1 S2 122.9(2) . .
S1 C1 S2 115.41(15) . .
C3 C2 S1 116.6(2) . .
C3 C2 I1 126.9(2) . .
S1 C2 I1 116.49(14) . .
C2 C3 S2 116.9(2) . .
C2 C3 I2 125.0(2) . .
S2 C3 I2 118.03(14) . .
C1 C4 S3 122.3(2) . .
C1 C4 S6 121.9(2) . .
S3 C4 S6 115.60(15) . .
C8 C5 S3 117.3(2) . .
C8 C5 S4 126.9(2) . .
S3 C5 S4 115.81(15) . .
C7 C6 S4 112.7(2) . .
C7 C6 H6A 109.0 . .
S4 C6 H6A 109.0 . .
C7 C6 H6B 109.0 . .
S4 C6 H6B 109.0 . .
H6A C6 H6B 107.8 . .
C6 C7 S5 114.5(2) . .
C6 C7 H7A 108.6 . .
S5 C7 H7A 108.6 . .
C6 C7 H7B 108.6 . .
S5 C7 H7B 108.6 . .
H7A C7 H7B 107.6 . .
C5 C8 S5 129.4(2) . .
C5 C8 S6 116.3(2) . .
S5 C8 S6 114.27(15) . .
O3A S1A O1A 113.43(12) . .
O3A S1A O2A 113.32(12) . .
O1A S1A O2A 112.18(11) . .
O3A S1A C3A 106.22(12) . .
O1A S1A C3A 105.36(11) . .
O2A S1A C3A 105.47(12) . .
C2A C1A C5A 120.4(2) . 2_554
C2A C1A H1A 119.8 . .
C5A C1A H1A 119.8 2_554 .
C1A C2A C3A 120.0(2) . .
C1A C2A H2A 120.0 . .
C3A C2A H2A 120.0 . .
C4A C3A C2A 121.2(2) . .
C4A C3A S1A 120.0(2) . .
C2A C3A S1A 118.83(19) . .
C3A C4A C5A 119.9(2) . .
C3A C4A H4A 120.0 . .
C5A C4A H4A 120.0 . .
C1A C5A C5A 119.3(3) 2_554 2_554
C1A C5A C4A 121.5(2) 2_554 .
C5A C5A C4A 119.2(3) 2_554 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C2 2.090(3) .
I2 C3 2.091(3) .
S1 C1 1.729(3) .
S1 C2 1.738(3) .
S2 C1 1.732(3) .
S2 C3 1.741(3) .
S3 C4 1.726(3) .
S3 C5 1.740(3) .
S4 C5 1.742(3) .
S4 C6 1.812(3) .
S5 C8 1.742(3) .
S5 C7 1.828(3) .
S6 C4 1.736(3) .
S6 C8 1.745(3) .
C1 C4 1.388(4) .
C2 C3 1.359(4) .
C5 C8 1.360(4) .
C6 C7 1.520(4) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
S1A O3A 1.453(2) .
S1A O1A 1.4630(19) .
S1A O2A 1.467(2) .
S1A C3A 1.788(3) .
C1A C2A 1.376(4) .
C1A C5A 1.421(4) 2_554
C1A H1A 0.9300 .
C2A C3A 1.418(4) .
C2A H2A 0.9300 .
C3A C4A 1.369(4) .
C4A C5A 1.426(3) .
C4A H4A 0.9300 .
C5A C1A 1.421(4) 2_554
C5A C5A 1.422(5) 2_554
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 S1 C1 C4 180.0(2) . .
C2 S1 C1 S2 3.09(17) . .
C3 S2 C1 C4 179.9(2) . .
C3 S2 C1 S1 -3.25(17) . .
C1 S1 C2 C3 -1.6(2) . .
C1 S1 C2 I1 -179.92(14) . .
S1 C2 C3 S2 -0.4(3) . .
I1 C2 C3 S2 177.71(13) . .
S1 C2 C3 I2 -179.10(13) . .
I1 C2 C3 I2 -1.0(3) . .
C1 S2 C3 C2 2.2(2) . .
C1 S2 C3 I2 -179.02(14) . .
S1 C1 C4 S3 -177.00(14) . .
S2 C1 C4 S3 -0.4(3) . .
S1 C1 C4 S6 -1.3(3) . .
S2 C1 C4 S6 175.38(14) . .
C5 S3 C4 C1 178.2(2) . .
C5 S3 C4 S6 2.20(17) . .
C8 S6 C4 C1 -178.3(2) . .
C8 S6 C4 S3 -2.25(17) . .
C4 S3 C5 C8 -1.3(2) . .
C4 S3 C5 S4 -179.37(15) . .
C6 S4 C5 C8 -29.0(3) . .
C6 S4 C5 S3 148.90(16) . .
C5 S4 C6 C7 62.4(2) . .
S4 C6 C7 S5 -68.0(3) . .
C8 S5 C7 C6 30.1(2) . .
S3 C5 C8 S5 -178.46(16) . .
S4 C5 C8 S5 -0.6(4) . .
S3 C5 C8 S6 -0.1(3) . .
S4 C5 C8 S6 177.78(15) . .
C7 S5 C8 C5 4.4(3) . .
C7 S5 C8 S6 -173.99(15) . .
C4 S6 C8 C5 1.4(2) . .
C4 S6 C8 S5 -179.99(15) . .
C5A C1A C2A C3A 0.1(4) 2_554 .
C1A C2A C3A C4A 0.5(4) . .
C1A C2A C3A S1A 179.7(2) . .
O3A S1A C3A C4A -32.4(2) . .
O1A S1A C3A C4A -153.0(2) . .
O2A S1A C3A C4A 88.2(2) . .
O3A S1A C3A C2A 148.4(2) . .
O1A S1A C3A C2A 27.8(2) . .
O2A S1A C3A C2A -91.0(2) . .
C2A C3A C4A C5A -0.6(4) . .
S1A C3A C4A C5A -179.80(19) . .
C3A C4A C5A C1A -179.4(2) . 2_554
C3A C4A C5A C5A 0.1(4) . 2_554
