#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:23:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180432 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/01/7210185.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_7210185
loop_
_publ_author_name
'Lieffrig, Julien'
'Pennec, Ronan Le'
'Jeannin, Olivier'
'Auban-Senzier, Pascale'
'Fourmigué, Marc'
_publ_section_title
;
 Toward chiral conductors: combining halogen bonding ability and chirality
 within a single tetrathiafulvalene molecule
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              4408
_journal_paper_doi               10.1039/c3ce40393a
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C11 H10 I2 S6'
_chemical_formula_sum            'C11 H10 I2 S6'
_chemical_formula_weight         588.35
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 99.6650(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.5711(2)
_cell_length_b                   7.2502(2)
_cell_length_c                   19.0229(5)
_cell_measurement_reflns_used    30730
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     893.42(4)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19753
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.51
_exptl_absorpt_coefficient_mu    4.205
_exptl_absorpt_correction_T_max  0.630
_exptl_absorpt_correction_T_min  0.379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.639
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.014(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         4046
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0148P)²+0.8193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0495
_refine_ls_wR_factor_ref         0.0530
_reflns_number_gt                3388
_reflns_number_total             4046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce40393a.txt
_cod_data_source_block           mol1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7210185
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 0.81125(4) 0.17064(5) 0.958785(14) 0.05301(8) Uani 1 1 d .
I2 I 0.67147(4) -0.32617(6) 0.911534(16) 0.06163(9) Uani 1 1 d .
S1 S 0.34494(18) 0.24466(17) 0.87118(7) 0.0560(3) Uani 1 1 d .
S2 S 0.23425(17) -0.14666(17) 0.84201(7) 0.0537(3) Uani 1 1 d .
S3 S -0.06950(18) 0.37149(18) 0.76186(6) 0.0530(3) Uani 1 1 d .
S4 S -0.19009(19) -0.01648(17) 0.73849(7) 0.0535(3) Uani 1 1 d .
S5 S -0.30011(18) 0.4980(2) 0.62022(7) 0.0589(3) Uani 1 1 d .
S6 S -0.47139(18) 0.05414(19) 0.60112(7) 0.0559(3) Uani 1 1 d .
C1 C 0.5311(6) 0.0791(6) 0.9001(2) 0.0448(10) Uani 1 1 d .
C2 C 0.4840(6) -0.0968(6) 0.8866(2) 0.0439(10) Uani 1 1 d .
C3 C 0.1681(6) 0.0860(6) 0.8241(2) 0.0455(10) Uani 1 1 d .
C4 C -0.0033(6) 0.1402(7) 0.7805(2) 0.0444(12) Uani 1 1 d .
C5 C -0.2371(7) 0.3178(7) 0.6813(2) 0.0452(10) Uani 1 1 d .
C6 C -0.2935(6) 0.1419(7) 0.6722(2) 0.0449(11) Uani 1 1 d .
C7 C -0.6308(8) 0.5767(8) 0.6878(3) 0.0685(14) Uani 1 1 d .
H7A H -0.5392 0.6714 0.7096 0.103 Uiso 1 1 calc R
H7B H -0.6161 0.4690 0.7176 0.103 Uiso 1 1 calc R
H7C H -0.7706 0.6201 0.6821 0.103 Uiso 1 1 calc R
C8 C -0.5776(7) 0.5282(7) 0.6151(3) 0.0564(12) Uani 1 1 d .
H8 H -0.6115 0.6389 0.5859 0.068 Uiso 1 1 calc R
C9 C -0.7127(7) 0.3758(8) 0.5760(3) 0.0624(14) Uani 1 1 d .
H9A H -0.8547 0.4179 0.5697 0.075 Uiso 1 1 calc R
H9B H -0.6768 0.3643 0.5288 0.075 Uiso 1 1 calc R
C10 C -0.7061(5) 0.1852(10) 0.6080(2) 0.0498(10) Uani 1 1 d .
H10 H -0.7190 0.1958 0.6584 0.060 Uiso 1 1 calc R
C11 C -0.8853(7) 0.0643(9) 0.5696(3) 0.0736(16) Uani 1 1 d .
H11A H -0.8775 -0.0561 0.5909 0.110 Uiso 1 1 calc R
H11B H -0.8746 0.0537 0.5201 0.110 Uiso 1 1 calc R
H11C H -1.0148 0.1204 0.5741 0.110 Uiso 1 1 calc R
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'
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
C1 S1 C3 94.5(2)
C2 S2 C3 94.4(2)
C4 S3 C5 93.5(2)
C6 S4 C4 93.4(2)
C5 S5 C8 104.4(2)
C6 S6 C10 102.5(2)
C2 C1 S1 118.3(3)
C2 C1 I1 124.3(3)
S1 C1 I1 117.3(2)
C1 C2 S2 117.4(3)
C1 C2 I2 128.0(3)
S2 C2 I2 114.6(2)
C4 C3 S2 123.7(3)
C4 C3 S1 122.3(4)
S2 C3 S1 113.9(2)
C3 C4 S3 124.0(4)
C3 C4 S4 122.7(4)
S3 C4 S4 113.2(2)
C6 C5 S5 126.8(3)
C6 C5 S3 116.2(3)
S5 C5 S3 116.9(3)
C5 C6 S6 125.7(3)
C5 C6 S4 117.9(3)
S6 C6 S4 116.4(3)
C8 C7 H7A 109.5
C8 C7 H7B 109.5
H7A C7 H7B 109.5
C8 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C7 C8 C9 113.9(4)
C7 C8 S5 111.0(3)
C9 C8 S5 115.7(4)
C7 C8 H8 105.0
C9 C8 H8 105.0
S5 C8 H8 105.0
C10 C9 C8 119.4(4)
C10 C9 H9A 107.5
C8 C9 H9A 107.5
C10 C9 H9B 107.5
C8 C9 H9B 107.5
H9A C9 H9B 107.0
C9 C10 C11 111.1(4)
C9 C10 S6 114.4(3)
C11 C10 S6 104.8(4)
C9 C10 H10 108.8
C11 C10 H10 108.8
S6 C10 H10 108.8
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.094(4)
I2 C2 2.076(4)
S1 C1 1.736(4)
S1 C3 1.768(4)
S2 C2 1.754(4)
S2 C3 1.761(5)
S3 C4 1.754(5)
S3 C5 1.773(4)
S4 C6 1.755(4)
S4 C4 1.762(4)
S5 C5 1.751(4)
S5 C8 1.823(5)
S6 C6 1.752(4)
S6 C10 1.835(5)
C1 C2 1.327(6)
C3 C4 1.341(5)
C5 C6 1.331(7)
C7 C8 1.525(7)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 C9 1.529(7)
C8 H8 0.9800
C9 C10 1.507(8)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.549(7)
C10 H10 0.9800
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
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
C3 S1 C1 C2 -6.2(4)
C3 S1 C1 I1 176.8(3)
S1 C1 C2 S2 -1.2(6)
I1 C1 C2 S2 175.5(2)
S1 C1 C2 I2 178.4(2)
I1 C1 C2 I2 -4.8(7)
C3 S2 C2 C1 8.0(4)
C3 S2 C2 I2 -171.8(2)
C2 S2 C3 C4 170.0(4)
C2 S2 C3 S1 -11.8(3)
C1 S1 C3 C4 -170.5(4)
C1 S1 C3 S2 11.3(3)
S2 C3 C4 S3 -179.5(3)
S1 C3 C4 S3 2.4(6)
S2 C3 C4 S4 2.9(6)
S1 C3 C4 S4 -175.2(3)
C5 S3 C4 C3 158.8(4)
C5 S3 C4 S4 -23.4(3)
C6 S4 C4 C3 -159.6(4)
C6 S4 C4 S3 22.5(3)
C8 S5 C5 C6 67.7(5)
C8 S5 C5 S3 -116.0(3)
C4 S3 C5 C6 15.5(4)
C4 S3 C5 S5 -161.2(3)
S5 C5 C6 S6 -8.5(7)
S3 C5 C6 S6 175.1(3)
S5 C5 C6 S4 174.2(3)
S3 C5 C6 S4 -2.2(5)
C10 S6 C6 C5 -58.6(5)
C10 S6 C6 S4 118.7(3)
C4 S4 C6 C5 -12.3(4)
C4 S4 C6 S6 170.1(3)
C5 S5 C8 C7 59.8(4)
C5 S5 C8 C9 -71.9(4)
C7 C8 C9 C10 -63.3(6)
S5 C8 C9 C10 67.1(5)
C8 C9 C10 C11 167.8(4)
C8 C9 C10 S6 -73.9(5)
C6 S6 C10 C9 80.9(3)
C6 S6 C10 C11 -157.2(4)
