#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:51:47 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179543 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/12/4501226.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_4501226
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         'C8 H4 I2 S6, Cl O4'
_chemical_formula_sum            'C8 H4 Cl I2 O4 S6'
_chemical_formula_weight         645.72
_chemical_name_common            EDT-TTFI2,ClO4
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 108.017(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6417(4)
_cell_length_b                   23.3523(9)
_cell_length_c                   9.7987(6)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.83
_cell_volume                     1662.85(16)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_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    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18690
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    4.704
_exptl_absorpt_correction_T_max  0.790
_exptl_absorpt_correction_T_min  0.433
_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    2.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1212
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.671
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0272
_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)+(0.0182P)²+3.2950P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0609
_reflns_number_gt                3428
_reflns_number_total             3798
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200934r_si_001.cif
_cod_data_source_block           clo4
_cod_original_cell_volume        1662.85(15)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4501226
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.83301(5) -0.187450(11) 0.60071(3) 0.05182(9) Uani 1 1 d .
I2 I 1.07044(3) -0.072220(11) 0.87064(2) 0.03712(7) Uani 1 1 d .
S1 S 0.65995(13) -0.07757(4) 0.40843(9) 0.03359(19) Uani 1 1 d .
S2 S 0.84265(12) 0.01167(3) 0.61139(9) 0.03045(17) Uani 1 1 d .
S3 S 0.63981(13) 0.10839(4) 0.38258(9) 0.03236(18) Uani 1 1 d .
S4 S 0.52077(15) 0.20537(4) 0.18478(11) 0.0443(2) Uani 1 1 d .
S5 S 0.28776(14) 0.09936(4) -0.05968(9) 0.0367(2) Uani 1 1 d .
S6 S 0.45337(12) 0.02084(3) 0.17855(9) 0.02894(17) Uani 1 1 d .
C1 C 0.6918(5) -0.00528(14) 0.4439(3) 0.0275(6) Uani 1 1 d .
C2 C 0.8170(5) -0.09976(14) 0.5689(4) 0.0314(7) Uani 1 1 d .
C3 C 0.9015(5) -0.05892(15) 0.6631(3) 0.0292(7) Uani 1 1 d .
C4 C 0.6046(4) 0.03627(14) 0.3450(3) 0.0276(6) Uani 1 1 d .
C5 C 0.5151(5) 0.13177(14) 0.2125(4) 0.0293(7) Uani 1 1 d .
C6 C 0.3132(5) 0.21279(16) 0.0349(4) 0.0402(8) Uani 1 1 d .
H6A H 0.2080 0.2033 0.0661 0.048 Uiso 1 1 calc R
H6B H 0.3003 0.2524 0.0035 0.048 Uiso 1 1 calc R
C7 C 0.3128(6) 0.17484(16) -0.0901(4) 0.0408(8) Uani 1 1 d .
H7A H 0.4271 0.1806 -0.1118 0.049 Uiso 1 1 calc R
H7B H 0.2130 0.1866 -0.1735 0.049 Uiso 1 1 calc R
C8 C 0.4252(4) 0.09104(14) 0.1168(3) 0.0266(6) Uani 1 1 d .
Cl1 Cl 0.77100(13) 0.15906(4) 0.78694(9) 0.03625(19) Uani 1 1 d .
O1 O 0.6071(4) 0.18832(14) 0.7052(4) 0.0660(9) Uani 1 1 d .
O2 O 0.8875(4) 0.15022(14) 0.6991(3) 0.0555(8) Uani 1 1 d .
O3 O 0.7224(4) 0.10437(12) 0.8333(3) 0.0532(8) Uani 1 1 d .
O4 O 0.8681(5) 0.19213(12) 0.9100(3) 0.0584(8) 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'
Cl Cl 0.1484 0.1585 '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
C1 S1 C2 95.44(16)
C1 S2 C3 95.48(16)
C4 S3 C5 95.68(16)
C5 S4 C6 99.41(17)
C8 S5 C7 102.19(17)
C4 S6 C8 96.13(16)
C4 C1 S1 122.4(3)
C4 C1 S2 122.4(3)
S1 C1 S2 115.13(18)
C3 C2 S1 117.4(3)
C3 C2 I1 127.2(3)
S1 C2 I1 115.09(19)
C2 C3 S2 116.4(3)
C2 C3 I2 126.1(3)
S2 C3 I2 117.04(18)
C1 C4 S6 123.5(3)
C1 C4 S3 121.6(3)
S6 C4 S3 114.91(18)
C8 C5 S3 116.9(2)
C8 C5 S4 127.8(3)
S3 C5 S4 115.34(19)
C7 C6 S4 112.6(3)
C7 C6 H6A 109.1
S4 C6 H6A 109.1
C7 C6 H6B 109.1
S4 C6 H6B 109.1
H6A C6 H6B 107.8
C6 C7 S5 114.3(3)
C6 C7 H7A 108.7
S5 C7 H7A 108.7
C6 C7 H7B 108.7
S5 C7 H7B 108.7
H7A C7 H7B 107.6
C5 C8 S5 129.0(3)
C5 C8 S6 115.9(2)
S5 C8 S6 115.10(19)
O4 Cl1 O2 109.1(2)
O4 Cl1 O1 110.4(2)
O2 Cl1 O1 109.3(2)
O4 Cl1 O3 109.24(18)
O2 Cl1 O3 109.3(2)
O1 Cl1 O3 109.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C2 2.069(3)
I2 C3 2.068(3)
S1 C1 1.726(3)
S1 C2 1.736(4)
S2 C1 1.735(3)
S2 C3 1.742(3)
S3 C4 1.727(3)
S3 C5 1.732(3)
S4 C5 1.743(3)
S4 C6 1.806(4)
S5 C8 1.735(3)
S5 C7 1.808(4)
S6 C4 1.720(3)
S6 C8 1.738(3)
C1 C4 1.387(5)
C2 C3 1.345(5)
C5 C8 1.363(5)
C6 C7 1.511(5)
C6 H6A 0.9700
C6 H6B 0.9700
C7 H7A 0.9700
C7 H7B 0.9700
Cl1 O4 1.431(3)
Cl1 O2 1.432(3)
Cl1 O1 1.434(3)
Cl1 O3 1.442(3)
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
C2 S1 C1 C4 176.4(3)
C2 S1 C1 S2 -2.9(2)
C3 S2 C1 C4 -176.5(3)
C3 S2 C1 S1 2.9(2)
C1 S1 C2 C3 1.9(3)
C1 S1 C2 I1 176.16(18)
S1 C2 C3 S2 -0.2(4)
I1 C2 C3 S2 -173.69(18)
S1 C2 C3 I2 172.37(17)
I1 C2 C3 I2 -1.1(5)
C1 S2 C3 C2 -1.6(3)
C1 S2 C3 I2 -174.85(18)
S1 C1 C4 S6 1.1(4)
S2 C1 C4 S6 -179.59(18)
S1 C1 C4 S3 -179.60(18)
S2 C1 C4 S3 -0.3(4)
C8 S6 C4 C1 -174.4(3)
C8 S6 C4 S3 6.3(2)
C5 S3 C4 C1 173.8(3)
C5 S3 C4 S6 -6.9(2)
C4 S3 C5 C8 5.0(3)
C4 S3 C5 S4 -174.9(2)
C6 S4 C5 C8 22.3(4)
C6 S4 C5 S3 -157.9(2)
C5 S4 C6 C7 -56.1(3)
S4 C6 C7 S5 71.0(3)
C8 S5 C7 C6 -40.4(3)
S3 C5 C8 S5 179.3(2)
S4 C5 C8 S5 -0.8(5)
S3 C5 C8 S6 -1.5(4)
S4 C5 C8 S6 178.4(2)
C7 S5 C8 C5 5.5(4)
C7 S5 C8 S6 -173.7(2)
C4 S6 C8 C5 -2.9(3)
C4 S6 C8 S5 176.43(19)
