# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Me2I2TTF
_database_code_depnum_ccdc_archive 'CCDC 1428793'
_audit_update_record             
;
2015-09-30 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;

_audit_creation_date             2015-09-30T10:23:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C8 H6 I2 S4'
_chemical_formula_sum            'C8 H6 I2 S4'
_chemical_formula_weight         484.17
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

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'

_cell_length_a                   6.2612(3)
_cell_length_b                   15.4368(8)
_cell_length_c                   6.6118(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.285(2)
_cell_angle_gamma                90
_cell_volume                     635.21(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4515
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.49
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    2.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.155
_exptl_absorpt_correction_T_max  0.513

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.3955  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_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_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_number            5319
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.639
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             1459
_reflns_number_gt                1404
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+6.6972P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1459
_refine_ls_number_parameters     71
_refine_ls_number_restraints     4
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_restrained_S_all      1.177
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.156
_refine_diff_density_min         -1.666
_refine_diff_density_rms         0.183

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
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_
_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9187(9) 0.0260(4) 0.5210(9) 0.0167(11) Uani 1 1 d . . . . .
C2 C 0.6097(8) 0.1372(4) 0.5009(9) 0.0163(11) Uani 1 1 d D . . . .
C3 C 0.5971(8) 0.0973(4) 0.6754(9) 0.0168(11) Uani 1 1 d D . . . .
S1 S 0.8163(2) 0.10934(10) 0.3554(2) 0.0212(3) Uani 1 1 d D . . . .
S2 S 0.7924(2) 0.01760(10) 0.7452(2) 0.0207(3) Uani 1 1 d . . . . .
C4A C 0.4236(10) 0.1136(4) 0.8296(9) 0.0145(11) Uani 0.9656(16) 1 d . . P A 1
H4A1 H 0.4523 0.0749 0.947 0.022 Uiso 0.9656(16) 1 calc R U P A 1
H4A2 H 0.4316 0.1739 0.8756 0.022 Uiso 0.9656(16) 1 calc R U P A 1
H4A3 H 0.2797 0.1018 0.7611 0.022 Uiso 0.9656(16) 1 calc R U P A 1
I1A I 0.40507(7) 0.23381(3) 0.37634(7) 0.02447(15) Uani 0.9656(16) 1 d . . P A
1
I1B I 0.3554(18) 0.1294(9) 0.8511(19) 0.02447(15) Uani 0.0344(16) 1 d D . P A 2
C4B C 0.451(6) 0.205(3) 0.418(7) 0.0145(11) Uani 0.0344(16) 1 d D . P A 2
H4B1 H 0.4904 0.2261 0.287 0.022 Uiso 0.0344(16) 1 calc R U P A 2
H4B2 H 0.3067 0.1798 0.3986 0.022 Uiso 0.0344(16) 1 calc R U P A 2
H4B3 H 0.4531 0.2535 0.514 0.022 Uiso 0.0344(16) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C1 1.349(11) 3_756 ?
C1 S2 1.760(6) . ?
C1 S1 1.764(6) . ?
C2 C3 1.318(8) . ?
C2 C4B 1.51(2) . ?
C2 S1 1.748(6) . ?
C2 I1A 2.077(5) . ?
C3 C4A 1.589(7) . ?
C3 S2 1.761(6) . ?
C3 I1B 2.066(2) . ?
C4A H4A1 0.98 . ?
C4A H4A2 0.98 . ?
C4A H4A3 0.98 . ?
C4B H4B1 0.98 . ?
C4B H4B2 0.98 . ?
C4B H4B3 0.98 . ?

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
_geom_angle_publ_flag
C1 C1 S2 123.2(6) 3_756 . ?
C1 C1 S1 122.6(6) 3_756 . ?
S2 C1 S1 114.2(3) . . ?
C3 C2 C4B 123.0(19) . . ?
C3 C2 S1 119.1(4) . . ?
C4B C2 S1 118.0(18) . . ?
C3 C2 I1A 126.1(4) . . ?
S1 C2 I1A 114.8(3) . . ?
C2 C3 C4A 126.8(5) . . ?
C2 C3 S2 116.7(4) . . ?
C4A C3 S2 116.5(4) . . ?
C2 C3 I1B 119.9(6) . . ?
S2 C3 I1B 123.4(5) . . ?
C2 S1 C1 94.5(3) . . ?
C1 S2 C3 95.2(3) . . ?
C3 C4A H4A1 109.5 . . ?
C3 C4A H4A2 109.5 . . ?
H4A1 C4A H4A2 109.5 . . ?
C3 C4A H4A3 109.5 . . ?
H4A1 C4A H4A3 109.5 . . ?
H4A2 C4A H4A3 109.5 . . ?
C2 C4B H4B1 109.5 . . ?
C2 C4B H4B2 109.5 . . ?
H4B1 C4B H4B2 109.5 . . ?
C2 C4B H4B3 109.5 . . ?
H4B1 C4B H4B3 109.5 . . ?
H4B2 C4B H4B3 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C2 C3 C4A 179.6(4) . . . . ?
I1A C2 C3 C4A 0.2(9) . . . . ?
C4B C2 C3 S2 178(2) . . . . ?
S1 C2 C3 S2 -0.5(7) . . . . ?
I1A C2 C3 S2 -180.0(3) . . . . ?
C4B C2 C3 I1B -1(2) . . . . ?
S1 C2 C3 I1B 179.7(6) . . . . ?
C3 C2 S1 C1 3.5(5) . . . . ?
C4B C2 S1 C1 -175(2) . . . . ?
I1A C2 S1 C1 -177.0(3) . . . . ?
C1 C1 S1 C2 175.4(7) 3_756 . . . ?
S2 C1 S1 C2 -5.1(4) . . . . ?
C1 C1 S2 C3 -175.6(7) 3_756 . . . ?
S1 C1 S2 C3 4.9(4) . . . . ?
C2 C3 S2 C1 -2.7(5) . . . . ?
C4A C3 S2 C1 177.1(4) . . . . ?
I1B C3 S2 C1 177.0(6) . . . . ?



# END of CIF
_chemical_name_systematic        (E)-Me2I2TTF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Me2I2TTF2Br
_database_code_depnum_ccdc_archive 'CCDC 1428794'
_audit_update_record             
;
2015-09-30 deposited with the CCDC.
2015-10-20 downloaded from the CCDC.
;

_audit_creation_date             2015-09-30T10:32:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_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_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   7.888(2)
_cell_length_b                   27.120(7)
_cell_length_c                   14.215(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.259(10)
_cell_angle_gamma                90
_cell_volume                     3028.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4515
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.49
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    2.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2020

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.528
_exptl_absorpt_correction_T_max  0.942

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.5008  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_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_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.0915
_diffrn_reflns_number            22381
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.502
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_Friedel_coverage         0
_reflns_number_total             6908
_reflns_number_gt                4628
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+10.6270P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6908
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.142
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.815
_refine_diff_density_min         -1.839
_refine_diff_density_rms         0.279

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?



# END of CIF
_chemical_name_systematic        '[(Z,E)Me2I2TTF]2 Br CH3CN'
_exptl_crystal_recrystallization_method electrocrystallization
_exptl_crystal_preparation       'Conducting properties'
