#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/87/7118702.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_7118702
loop_
_publ_author_name
'Jeannin, Olivier'
'Canadell, Enric'
'Auban-Senzier, Pascale'
'Fourmigué, Marc'
_publ_section_title
;
 Correlating conduction properties with the molecular symmetry:
 segregation of Z and E isomers in the charge-assisted, halogen-bonded
 cocrystal [(Z,E)-Me2I2TTF]2Br.
;
_journal_issue                   2
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              308
_journal_page_last               311
_journal_paper_doi               10.1039/c5cc08176a
_journal_volume                  52
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         '2(C8 H6 I2 S4), C2 H3 N, Br'
_chemical_formula_sum            'C18 H15 Br I4 N S8'
_chemical_formula_weight         1089.3
_chemical_name_systematic        '[(Z,E)Me2I2TTF]2 Br CH3CN'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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 - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-09-30T10:32:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-09-30 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.259(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.888(2)
_cell_length_b                   27.120(7)
_cell_length_c                   14.215(4)
_cell_measurement_reflns_used    4515
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.1
_cell_measurement_wavelength     0.71073
_cell_volume                     3028.1(14)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      -0.103759
_diffrn_orient_matrix_UB_12      0.013778
_diffrn_orient_matrix_UB_13      0.100156
_diffrn_orient_matrix_UB_21      -0.097187
_diffrn_orient_matrix_UB_22      -0.047203
_diffrn_orient_matrix_UB_23      -0.058668
_diffrn_orient_matrix_UB_31      0.07488
_diffrn_orient_matrix_UB_32      -0.042173
_diffrn_orient_matrix_UB_33      0.098385
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.0915
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22381
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.99
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_min         1.502
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.999
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.528
_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    2.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2020
_exptl_crystal_preparation       'Conducting properties'
_exptl_crystal_recrystallization_method electrocrystallization
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.815
_refine_diff_density_min         -1.839
_refine_diff_density_rms         0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     289
_refine_ls_number_reflns         6908
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0535P)²+10.6270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.142
_reflns_Friedel_coverage         0
_reflns_number_gt                4628
_reflns_number_total             6908
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc08176a2.cif
_cod_data_source_block           Me2I2TTF2Br
_cod_original_cell_volume        3028.1(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7118702
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.6791(12) 0.4693(3) 0.9996(6) 0.021(2) Uani 1 1 d . .
C2 C 0.8337(11) 0.5524(3) 0.9913(7) 0.021(2) Uani 1 1 d . .
C3 C 0.7963(12) 0.5404(3) 0.9003(7) 0.024(2) Uani 1 1 d . .
C4 C 0.8528(13) 0.5728(4) 0.8147(6) 0.0294(17) Uani 1 1 d . .
H4A H 0.9292 0.5983 0.8388 0.044 Uiso 1 1 calc R U
H4B H 0.7541 0.5874 0.7813 0.044 Uiso 1 1 calc R U
H4C H 0.9092 0.5521 0.7725 0.044 Uiso 1 1 calc R U
C5 C 0.6137(11) 0.4247(3) 1.0259(6) 0.020(2) Uani 1 1 d . .
C6 C 0.5212(11) 0.3474(4) 1.1105(7) 0.023(2) Uani 1 1 d . .
C7 C 0.4878(11) 0.3362(3) 1.0195(7) 0.023(2) Uani 1 1 d . .
C8 C 0.4143(13) 0.2892(4) 0.9749(6) 0.0294(17) Uani 1 1 d . .
H8A H 0.3932 0.2661 1.0236 0.044 Uiso 1 1 calc R U
H8B H 0.4938 0.2752 0.9351 0.044 Uiso 1 1 calc R U
H8C H 0.3095 0.2965 0.9378 0.044 Uiso 1 1 calc R U
C9 C 0.9620(11) 0.5219(3) 1.4854(6) 0.0173(19) Uani 1 1 d . .
C10 C 0.8292(11) 0.6077(3) 1.4742(7) 0.022(2) Uani 1 1 d . .
C11 C 0.8180(11) 0.5918(4) 1.3847(7) 0.024(2) Uani 1 1 d . .
C12 C 0.7410(11) 0.6194(4) 1.2970(6) 0.024(2) Uani 1 1 d . .
H12A H 0.6544 0.6416 1.3146 0.036 Uiso 1 1 calc R U
H12B H 0.6919 0.5962 1.2514 0.036 Uiso 1 1 calc R U
H12C H 0.8286 0.6379 1.2701 0.036 Uiso 1 1 calc R U
C13 C 1.4594(11) 0.5218(4) 1.4889(6) 0.023(2) Uani 1 1 d . .
C14 C 1.3181(12) 0.5970(3) 1.4023(6) 0.022(2) Uani 1 1 d . .
C15 C 1.3297(11) 0.6103(3) 1.4937(7) 0.021(2) Uani 1 1 d . .
C16 C 1.2720(11) 0.6604(4) 1.5326(6) 0.021(2) Uani 1 1 d . .
H16A H 1.368 0.6823 1.5414 0.032 Uiso 1 1 calc R U
H16B H 1.2258 0.6553 1.592 0.032 Uiso 1 1 calc R U
H16C H 1.1866 0.6748 1.4885 0.032 Uiso 1 1 calc R U
C17 C 2.0467(13) 0.6910(5) 1.7711(8) 0.038(3) Uani 1 1 d . .
C18 C 2.0334(18) 0.7347(5) 1.8301(11) 0.063(4) Uani 1 1 d . .
H18A H 2.0326 0.7248 1.895 0.095 Uiso 1 1 calc R U
H18B H 1.93 0.7519 1.8106 0.095 Uiso 1 1 calc R U
H18C H 2.129 0.7559 1.8237 0.095 Uiso 1 1 calc R U
N1 N 2.0549(13) 0.6559(4) 1.7281(7) 0.048(3) Uani 1 1 d . .
S1 S 0.7702(3) 0.51279(9) 1.07864(16) 0.0221(5) Uani 1 1 d . .
S2 S 0.6873(3) 0.48458(9) 0.88086(17) 0.0259(5) Uani 1 1 d . .
S3 S 0.5365(3) 0.38269(9) 0.93931(17) 0.0233(5) Uani 1 1 d . .
S4 S 0.6086(3) 0.40428(9) 1.14048(17) 0.0250(5) Uani 1 1 d . .
S5 S 0.9222(3) 0.56937(9) 1.56086(16) 0.0220(5) Uani 1 1 d . .
S6 S 0.8961(3) 0.53283(9) 1.36684(16) 0.0236(5) Uani 1 1 d . .
S7 S 1.3903(3) 0.53822(9) 1.37236(16) 0.0227(5) Uani 1 1 d . .
S8 S 1.4191(3) 0.56612(9) 1.57411(16) 0.0237(5) Uani 1 1 d . .
Br1 Br 1.62216(13) 0.77830(4) 1.61308(7) 0.0264(2) Uani 1 1 d . .
I1 I 0.95666(8) 0.61793(2) 1.03695(5) 0.02570(17) Uani 1 1 d . .
I2 I 0.46882(8) 0.29911(3) 1.21964(5) 0.02986(18) Uani 1 1 d . .
I3 I 0.75105(8) 0.67722(2) 1.52038(5) 0.02393(17) Uani 1 1 d . .
I4 I 1.23213(8) 0.64300(2) 1.28963(4) 0.02490(17) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 '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
C5 C1 S1 124.2(7) .
C5 C1 S2 121.3(7) .
S1 C1 S2 114.5(5) .
C3 C2 S1 118.9(7) .
C3 C2 I1 124.0(7) .
S1 C2 I1 117.0(5) .
C2 C3 C4 123.4(9) .
C2 C3 S2 115.1(7) .
C4 C3 S2 121.5(7) .
C3 C4 H4A 109.5 .
C3 C4 H4B 109.5 .
H4A C4 H4B 109.5 .
C3 C4 H4C 109.5 .
H4A C4 H4C 109.5 .
H4B C4 H4C 109.5 .
C1 C5 S4 125.5(7) .
C1 C5 S3 119.7(7) .
S4 C5 S3 114.8(5) .
C7 C6 S4 118.8(7) .
C7 C6 I2 122.8(7) .
S4 C6 I2 118.4(5) .
C6 C7 C8 129.2(9) .
C6 C7 S3 115.4(7) .
C8 C7 S3 115.4(7) .
C7 C8 H8A 109.5 .
C7 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
C7 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
C9 C9 S5 123.8(9) 3_768
C9 C9 S6 121.4(9) 3_768
S5 C9 S6 114.8(5) .
C11 C10 S5 118.1(7) .
C11 C10 I3 126.1(7) .
S5 C10 I3 115.8(5) .
C10 C11 C12 127.0(9) .
C10 C11 S6 116.2(7) .
C12 C11 S6 116.8(7) .
C11 C12 H12A 109.5 .
C11 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C11 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C13 C13 S7 122.5(10) 3_868
C13 C13 S8 122.8(9) 3_868
S7 C13 S8 114.7(5) .
C15 C14 S7 118.8(7) .
C15 C14 I4 124.6(7) .
S7 C14 I4 116.4(5) .
C14 C15 C16 125.7(8) .
C14 C15 S8 115.7(7) .
C16 C15 S8 118.6(7) .
C15 C16 H16A 109.5 .
C15 C16 H16B 109.5 .
H16A C16 H16B 109.5 .
C15 C16 H16C 109.5 .
H16A C16 H16C 109.5 .
H16B C16 H16C 109.5 .
N1 C17 C18 177.2(13) .
C17 C18 H18A 109.5 .
C17 C18 H18B 109.5 .
H18A C18 H18B 109.5 .
C17 C18 H18C 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
C1 S1 C2 94.9(4) .
C1 S2 C3 96.5(5) .
C5 S3 C7 95.4(4) .
C5 S4 C6 95.6(4) .
C9 S5 C10 95.5(4) .
C11 S6 C9 95.4(4) .
C13 S7 C14 94.7(4) .
C13 S8 C15 96.0(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C5 1.379(13) .
C1 S1 1.739(9) .
C1 S2 1.745(9) .
C2 C3 1.339(13) .
C2 S1 1.750(10) .
C2 I1 2.099(9) .
C3 C4 1.597(13) .
C3 S2 1.751(10) .
C4 H4A 0.96 .
C4 H4B 0.96 .
C4 H4C 0.96 .
C5 S4 1.724(9) .
C5 S3 1.746(9) .
C6 C7 1.332(13) .
C6 S4 1.728(10) .
C6 I2 2.100(9) .
C7 C8 1.515(13) .
C7 S3 1.765(10) .
C8 H8A 0.96 .
C8 H8B 0.96 .
C8 H8C 0.96 .
C9 C9 1.378(17) 3_768
C9 S5 1.723(9) .
C9 S6 1.743(8) .
C10 C11 1.340(13) .
C10 S5 1.724(10) .
C10 I3 2.106(9) .
C11 C12 1.531(13) .
C11 S6 1.740(10) .
C12 H12A 0.96 .
C12 H12B 0.96 .
C12 H12C 0.96 .
C13 C13 1.367(18) 3_868
C13 S7 1.753(9) .
C13 S8 1.757(10) .
C14 C15 1.344(13) .
C14 S7 1.758(10) .
C14 I4 2.093(9) .
C15 C16 1.552(13) .
C15 S8 1.758(9) .
C16 H16A 0.96 .
C16 H16B 0.96 .
C16 H16C 0.96 .
C17 N1 1.136(15) .
C17 C18 1.460(18) .
C18 H18A 0.96 .
C18 H18B 0.96 .
C18 H18C 0.96 .
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
S1 C2 C3 C4 -178.0(7) .
I1 C2 C3 C4 4.7(13) .
S1 C2 C3 S2 -0.7(10) .
I1 C2 C3 S2 -178.0(4) .
S1 C1 C5 S4 0.5(13) .
S2 C1 C5 S4 176.6(5) .
S1 C1 C5 S3 -176.4(5) .
S2 C1 C5 S3 -0.3(11) .
S4 C6 C7 C8 179.1(8) .
I2 C6 C7 C8 -1.9(14) .
S4 C6 C7 S3 -0.7(11) .
I2 C6 C7 S3 178.4(4) .
S5 C10 C11 C12 -179.9(7) .
I3 C10 C11 C12 -2.3(15) .
S5 C10 C11 S6 1.2(11) .
I3 C10 C11 S6 178.9(5) .
S7 C14 C15 C16 -179.9(7) .
I4 C14 C15 C16 3.9(14) .
S7 C14 C15 S8 0.3(10) .
I4 C14 C15 S8 -175.9(5) .
C5 C1 S1 C2 174.8(8) .
S2 C1 S1 C2 -1.5(6) .
C3 C2 S1 C1 1.3(8) .
I1 C2 S1 C1 178.9(5) .
C5 C1 S2 C3 -175.2(8) .
S1 C1 S2 C3 1.3(6) .
C2 C3 S2 C1 -0.4(8) .
C4 C3 S2 C1 177.0(7) .
C1 C5 S3 C7 177.1(8) .
S4 C5 S3 C7 -0.1(6) .
C6 C7 S3 C5 0.4(8) .
C8 C7 S3 C5 -179.4(7) .
C1 C5 S4 C6 -177.2(8) .
S3 C5 S4 C6 -0.2(6) .
C7 C6 S4 C5 0.5(9) .
I2 C6 S4 C5 -178.5(5) .
C9 C9 S5 C10 -179.5(11) 3_768
S6 C9 S5 C10 -0.2(6) .
C11 C10 S5 C9 -0.6(9) .
I3 C10 S5 C9 -178.6(5) .
C10 C11 S6 C9 -1.1(8) .
C12 C11 S6 C9 179.9(7) .
C9 C9 S6 C11 180.0(10) 3_768
S5 C9 S6 C11 0.7(6) .
C13 C13 S7 C14 -176.4(11) 3_868
S8 C13 S7 C14 2.7(6) .
C15 C14 S7 C13 -1.8(8) .
I4 C14 S7 C13 174.7(5) .
C13 C13 S8 C15 176.4(11) 3_868
S7 C13 S8 C15 -2.6(6) .
C14 C15 S8 C13 1.4(8) .
C16 C15 S8 C13 -178.5(7) .
