# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_EDOI
_database_code_depnum_ccdc_archive 'CCDC 1590291'
_audit_update_record             
;
2017-12-11 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        EDO-TTF-I
_chemical_name_common            4,5-ethylenedioxy-4'-iodotetrathiafulvalene
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H5 I O2 S4'
_chemical_formula_sum            'C8 H5 I O2 S4'
_chemical_formula_weight         388.26

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1944(5)
_cell_length_b                   14.4974(8)
_cell_length_c                   19.7587(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2347.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100

_cell_measurement_reflns_used    4835

_cell_measurement_theta_min      2.99

_cell_measurement_theta_max      28.51


_exptl_crystal_description       plate

_exptl_crystal_colour            orange

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.197
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.414
_shelx_estimated_absorpt_T_min   0.495
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.374

_exptl_absorpt_correction_T_max  0.876

_exptl_absorpt_process_details   SADABS


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            13608
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.061
_diffrn_reflns_theta_max         29.353
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3036
_reflns_number_gt                2512
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    sir2014

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0226P)²+1.3623P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3036
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0542
_refine_ls_wR_factor_gt          0.0506
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
I15 I 0.34016(2) 0.34466(2) 0.29876(2) 0.02259(6) Uani 1 1 d . . . . .
S3 S 0.22454(7) -0.00610(4) 0.49537(3) 0.01425(13) Uani 1 1 d . . . . .
S4 S 0.34883(8) 0.15457(4) 0.39014(3) 0.01628(13) Uani 1 1 d . . . . .
S5 S 0.43664(8) 0.07777(4) 0.60225(3) 0.01728(13) Uani 1 1 d . . . . .
S6 S 0.56858(8) 0.22626(4) 0.49563(3) 0.01895(14) Uani 1 1 d . . . . .
O11 O 0.0802(2) -0.10672(13) 0.59086(9) 0.0219(4) Uani 1 1 d . . . . .
O12 O 0.2799(3) -0.02172(13) 0.69480(9) 0.0239(4) Uani 1 1 d . . . . .
C1 C 0.3653(3) 0.08033(17) 0.51795(12) 0.0132(5) Uani 1 1 d . . . . .
C2 C 0.4200(3) 0.14388(16) 0.47370(12) 0.0138(5) Uani 1 1 d . . . . .
C7 C 0.1914(3) -0.03820(17) 0.57973(12) 0.0159(5) Uani 1 1 d . . . . .
C8 C 0.4154(3) 0.26949(17) 0.38294(13) 0.0170(5) Uani 1 1 d . . . . .
C9 C 0.2842(3) -0.00023(17) 0.62721(12) 0.0168(5) Uani 1 1 d . . . . .
C10 C 0.5134(3) 0.30204(17) 0.43081(13) 0.0180(5) Uani 1 1 d . . . . .
H10 H 0.5540 0.3671 0.4298 0.022 Uiso 1 1 calc R U . . .
C13 C 0.1143(4) -0.1508(2) 0.65413(16) 0.0321(7) Uani 1 1 d . . . . .
H13A H 0.2142 -0.1900 0.6495 0.039 Uiso 1 1 calc R U . . .
H13B H 0.0210 -0.1918 0.6668 0.039 Uiso 1 1 calc R U . . .
C14 C 0.1405(4) -0.0808(2) 0.70853(15) 0.0358(8) Uani 1 1 d . . . . .
H14A H 0.0403 -0.0418 0.7129 0.043 Uiso 1 1 calc R U . . .
H14B H 0.1578 -0.1132 0.7526 0.043 Uiso 1 1 calc R U . . .


_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
I15 C8 2.082(3) . ?
S3 C7 1.752(3) . ?
S3 C1 1.760(2) . ?
S4 C2 1.758(2) . ?
S4 C8 1.759(3) . ?
S5 C9 1.756(3) . ?
S5 C1 1.766(2) . ?
S6 C10 1.747(3) . ?
S6 C2 1.760(2) . ?
O11 C7 1.366(3) . ?
O11 C13 1.432(3) . ?
O12 C9 1.372(3) . ?
O12 C14 1.454(4) . ?
C1 C2 1.347(3) . ?
C7 C9 1.327(4) . ?
C8 C10 1.328(4) . ?
C10 H10 1.0000 . ?
C13 C14 1.494(5) . ?
C13 H13A 1.0000 . ?
C13 H13B 1.0000 . ?
C14 H14A 1.0000 . ?
C14 H14B 1.0000 . ?

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
C7 S3 C1 92.84(12) . . ?
C2 S4 C8 93.24(12) . . ?
C9 S5 C1 92.45(12) . . ?
C10 S6 C2 93.86(12) . . ?
C7 O11 C13 109.6(2) . . ?
C9 O12 C14 109.6(2) . . ?
C2 C1 S3 122.72(19) . . ?
C2 C1 S5 121.09(19) . . ?
S3 C1 S5 116.17(14) . . ?
C1 C2 S4 124.02(19) . . ?
C1 C2 S6 122.33(19) . . ?
S4 C2 S6 113.64(13) . . ?
C9 C7 O11 124.8(2) . . ?
C9 C7 S3 118.28(19) . . ?
O11 C7 S3 116.73(18) . . ?
C10 C8 S4 117.8(2) . . ?
C10 C8 I15 124.22(19) . . ?
S4 C8 I15 117.93(14) . . ?
C7 C9 O12 125.4(2) . . ?
C7 C9 S5 118.44(19) . . ?
O12 C9 S5 115.96(18) . . ?
C8 C10 S6 117.1(2) . . ?
C8 C10 H10 121.5 . . ?
S6 C10 H10 121.5 . . ?
O11 C13 C14 110.7(2) . . ?
O11 C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
O11 C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
O12 C14 C13 112.3(2) . . ?
O12 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
O12 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?

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
C7 S3 C1 C2 -168.8(2) . . . . ?
C7 S3 C1 S5 12.92(15) . . . . ?
C9 S5 C1 C2 168.2(2) . . . . ?
C9 S5 C1 S3 -13.40(16) . . . . ?
S3 C1 C2 S4 4.7(3) . . . . ?
S5 C1 C2 S4 -177.03(13) . . . . ?
S3 C1 C2 S6 -176.62(13) . . . . ?
S5 C1 C2 S6 1.6(3) . . . . ?
C8 S4 C2 C1 158.9(2) . . . . ?
C8 S4 C2 S6 -19.85(16) . . . . ?
C10 S6 C2 C1 -158.4(2) . . . . ?
C10 S6 C2 S4 20.36(15) . . . . ?
C13 O11 C7 C9 -18.3(4) . . . . ?
C13 O11 C7 S3 156.0(2) . . . . ?
C1 S3 C7 C9 -7.0(2) . . . . ?
C1 S3 C7 O11 178.4(2) . . . . ?
C2 S4 C8 C10 11.6(2) . . . . ?
C2 S4 C8 I15 -169.87(14) . . . . ?
O11 C7 C9 O12 -1.9(4) . . . . ?
S3 C7 C9 O12 -176.14(19) . . . . ?
O11 C7 C9 S5 172.9(2) . . . . ?
S3 C7 C9 S5 -1.3(3) . . . . ?
C14 O12 C9 C7 -9.5(4) . . . . ?
C14 O12 C9 S5 175.5(2) . . . . ?
C1 S5 C9 C7 8.8(2) . . . . ?
C1 S5 C9 O12 -175.92(19) . . . . ?
S4 C8 C10 S6 0.9(3) . . . . ?
I15 C8 C10 S6 -177.53(13) . . . . ?
C2 S6 C10 C8 -12.9(2) . . . . ?
C7 O11 C13 C14 47.8(3) . . . . ?
C9 O12 C14 C13 39.8(3) . . . . ?
O11 C13 C14 O12 -62.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 S3 1.00 2.86 3.724(3) 144.6 3_556
C14 H14A I15 1.00 3.30 4.219(4) 152.9 3_456
C14 H14B S4 1.00 2.78 3.745(3) 161.6 2
C10 H10 S3 1.00 2.86 3.724(3) 144.6 3_556
C14 H14A I15 1.00 3.30 4.219(4) 152.9 3_456
C14 H14B S4 1.00 2.78 3.745(3) 161.6 2

_refine_diff_density_max         0.825
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.108

_shelxl_version_number           2014-3



_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_(EDO-TTF-I)2PF6_100K
_database_code_depnum_ccdc_archive 'CCDC 1590293'
_audit_update_record             
;
2017-12-11 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            (EDO-TTF-I)2PF6
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H5 I O2 S4), F6 P'
_chemical_formula_sum            'C16 H10 F6 I2 O4 P S8'
_chemical_formula_weight         921.49

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4961(6)
_cell_length_b                   7.4115(7)
_cell_length_c                   14.3958(13)
_cell_angle_alpha                92.1840(10)
_cell_angle_beta                 76.2630(10)
_cell_angle_gamma                110.4120(10)
_cell_volume                     630.24(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    100

_cell_measurement_reflns_used    2289

_cell_measurement_theta_min      2.92

_cell_measurement_theta_max      29.11


_exptl_crystal_description       plate

_exptl_crystal_colour            black

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.428
_exptl_crystal_F_000             441
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.293
_shelx_estimated_absorpt_T_min   0.693
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.635

_exptl_absorpt_correction_T_max  0.908

_exptl_absorpt_process_details   SADABS


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            3925
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0131
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.458
_diffrn_reflns_theta_max         29.277
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             2999
_reflns_number_gt                2658
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    sir2014

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0318P)²+0.2076P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2999
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0570
_refine_ls_wR_factor_gt          0.0547
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
I15 I 0.21148(3) 0.82588(3) 0.21141(2) 0.01243(6) Uani 1 1 d . . . . .
S3 S 0.19003(12) 0.66089(10) 0.66130(5) 0.01274(14) Uani 1 1 d . . . . .
S4 S 0.22218(11) 0.75335(10) 0.43397(5) 0.01257(14) Uani 1 1 d . . . . .
S5 S 0.68358(12) 0.73267(10) 0.60680(5) 0.01287(14) Uani 1 1 d . . . . .
S6 S 0.71236(12) 0.82909(11) 0.39371(5) 0.01359(14) Uani 1 1 d . . . . .
O11 O 0.1896(3) 0.5885(3) 0.84140(14) 0.0137(4) Uani 1 1 d . . . . .
O12 O 0.6685(3) 0.6487(3) 0.78500(14) 0.0145(4) Uani 1 1 d . . . . .
C1 C 0.4415(5) 0.7247(4) 0.5720(2) 0.0111(5) Uani 1 1 d . . . . .
C2 C 0.4540(5) 0.7664(4) 0.4786(2) 0.0116(5) Uani 1 1 d . . . . .
C7 C 0.3185(5) 0.6343(4) 0.7511(2) 0.0116(5) Uani 1 1 d . . . . .
C8 C 0.3796(5) 0.8122(4) 0.31540(19) 0.0119(5) Uani 1 1 d . . . . .
C9 C 0.5420(5) 0.6642(4) 0.72571(19) 0.0121(5) Uani 1 1 d . . . . .
C10 C 0.6003(5) 0.8465(4) 0.2975(2) 0.0137(6) Uani 1 1 d . . . . .
H10 H 0.6985 0.8811 0.2311 0.016 Uiso 1 1 calc R U . . .
C13 C 0.3350(5) 0.6431(4) 0.9089(2) 0.0139(6) Uani 1 1 d . . . . .
H13A H 0.2445 0.5891 0.9745 0.017 Uiso 1 1 calc R U . . .
H13B H 0.3971 0.7867 0.9109 0.017 Uiso 1 1 calc R U . . .
C14 C 0.5274(5) 0.5667(4) 0.8784(2) 0.0152(6) Uani 1 1 d . . . . .
H14A H 0.6215 0.5989 0.9266 0.018 Uiso 1 1 calc R U . . .
H14B H 0.4644 0.4232 0.8761 0.018 Uiso 1 1 calc R U . . .
P16 P 0.0000 0.0000 0.0000 0.0116(2) Uani 1 2 d S . P . .
F17 F 0.2681(3) 0.0700(3) -0.01217(14) 0.0222(4) Uani 1 1 d . . . . .
F18 F 0.0275(3) 0.2036(3) -0.04581(13) 0.0227(4) Uani 1 1 d . . . . .
F19 F -0.0281(3) 0.0839(3) 0.10445(12) 0.0229(4) Uani 1 1 d . . . . .


_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
I15 C8 2.076(3) . ?
S3 C7 1.747(3) . ?
S3 C1 1.748(3) . ?
S4 C2 1.744(3) . ?
S4 C8 1.751(3) . ?
S5 C9 1.740(3) . ?
S5 C1 1.742(3) . ?
S6 C10 1.739(3) . ?
S6 C2 1.747(3) . ?
O11 C7 1.351(3) . ?
O11 C13 1.462(3) . ?
O12 C9 1.350(3) . ?
O12 C14 1.450(3) . ?
C1 C2 1.368(4) . ?
C7 C9 1.349(4) . ?
C8 C10 1.327(4) . ?
C10 H10 1.0000 . ?
C13 C14 1.513(4) . ?
C13 H13A 1.0000 . ?
C13 H13B 1.0000 . ?
C14 H14A 1.0000 . ?
C14 H14B 1.0000 . ?
P16 F19 1.5994(18) 2 ?
P16 F19 1.5994(18) . ?
P16 F17 1.6014(17) . ?
P16 F17 1.6014(17) 2 ?
P16 F18 1.6052(17) 2 ?
P16 F18 1.6052(17) . ?

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
C7 S3 C1 93.83(13) . . ?
C2 S4 C8 94.43(13) . . ?
C9 S5 C1 94.07(13) . . ?
C10 S6 C2 94.95(14) . . ?
C7 O11 C13 109.4(2) . . ?
C9 O12 C14 111.0(2) . . ?
C2 C1 S5 120.1(2) . . ?
C2 C1 S3 123.3(2) . . ?
S5 C1 S3 116.65(16) . . ?
C1 C2 S4 124.4(2) . . ?
C1 C2 S6 120.3(2) . . ?
S4 C2 S6 115.27(15) . . ?
C9 C7 O11 124.2(2) . . ?
C9 C7 S3 117.6(2) . . ?
O11 C7 S3 118.2(2) . . ?
C10 C8 S4 117.9(2) . . ?
C10 C8 I15 123.8(2) . . ?
S4 C8 I15 118.30(15) . . ?
C7 C9 O12 125.8(3) . . ?
C7 C9 S5 117.8(2) . . ?
O12 C9 S5 116.4(2) . . ?
C8 C10 S6 117.5(2) . . ?
C8 C10 H10 121.3 . . ?
S6 C10 H10 121.3 . . ?
O11 C13 C14 109.9(2) . . ?
O11 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
O11 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
O12 C14 C13 111.2(2) . . ?
O12 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
O12 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
F19 P16 F19 180.0 2 . ?
F19 P16 F17 90.02(10) 2 . ?
F19 P16 F17 89.98(10) . . ?
F19 P16 F17 89.98(10) 2 2 ?
F19 P16 F17 90.02(10) . 2 ?
F17 P16 F17 180.0 . 2 ?
F19 P16 F18 90.16(10) 2 2 ?
F19 P16 F18 89.84(10) . 2 ?
F17 P16 F18 90.09(9) . 2 ?
F17 P16 F18 89.92(9) 2 2 ?
F19 P16 F18 89.84(10) 2 . ?
F19 P16 F18 90.16(10) . . ?
F17 P16 F18 89.91(9) . . ?
F17 P16 F18 90.08(9) 2 . ?
F18 P16 F18 180.0 2 . ?

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
C9 S5 C1 C2 -179.2(2) . . . . ?
C9 S5 C1 S3 0.50(19) . . . . ?
C7 S3 C1 C2 179.9(3) . . . . ?
C7 S3 C1 S5 0.17(18) . . . . ?
S5 C1 C2 S4 177.10(16) . . . . ?
S3 C1 C2 S4 -2.6(4) . . . . ?
S5 C1 C2 S6 -0.3(4) . . . . ?
S3 C1 C2 S6 179.99(15) . . . . ?
C8 S4 C2 C1 -176.8(3) . . . . ?
C8 S4 C2 S6 0.75(18) . . . . ?
C10 S6 C2 C1 177.0(3) . . . . ?
C10 S6 C2 S4 -0.69(19) . . . . ?
C13 O11 C7 C9 20.0(4) . . . . ?
C13 O11 C7 S3 -158.80(19) . . . . ?
C1 S3 C7 C9 -1.1(2) . . . . ?
C1 S3 C7 O11 177.8(2) . . . . ?
C2 S4 C8 C10 -0.6(3) . . . . ?
C2 S4 C8 I15 179.81(16) . . . . ?
O11 C7 C9 O12 1.7(5) . . . . ?
S3 C7 C9 O12 -179.4(2) . . . . ?
O11 C7 C9 S5 -177.1(2) . . . . ?
S3 C7 C9 S5 1.7(3) . . . . ?
C14 O12 C9 C7 8.6(4) . . . . ?
C14 O12 C9 S5 -172.45(19) . . . . ?
C1 S5 C9 C7 -1.3(3) . . . . ?
C1 S5 C9 O12 179.7(2) . . . . ?
S4 C8 C10 S6 0.2(3) . . . . ?
I15 C8 C10 S6 179.78(14) . . . . ?
C2 S6 C10 C8 0.3(3) . . . . ?
C7 O11 C13 C14 -49.5(3) . . . . ?
C9 O12 C14 C13 -39.1(3) . . . . ?
O11 C13 C14 O12 61.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 F19 1.00 2.36 3.296(3) 156.5 1_665
C13 H13B I15 1.00 3.31 4.145(3) 141.7 2_676
C13 H13B F17 1.00 2.64 3.456(4) 139.3 1_566
C14 H14B I15 1.00 3.27 3.889(3) 121.6 2_666
C10 H10 F19 1.00 2.36 3.296(3) 156.5 1_665
C13 H13B I15 1.00 3.31 4.145(3) 141.7 2_676
C13 H13B F17 1.00 2.64 3.456(4) 139.3 1_566
C14 H14B I15 1.00 3.27 3.889(3) 121.6 2_666

_refine_diff_density_max         1.021
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.119

_shelxl_version_number           2014-3



_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_(EDO-TTF-I)2PF6_300K
_database_code_depnum_ccdc_archive 'CCDC 1590294'
_audit_update_record             
;
2017-12-11 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            (EDO-TTF-I)2PF6
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H5 I O2 S4), F6 P'
_chemical_formula_sum            'C16 H10 F6 I2 O4 P S8'
_chemical_formula_weight         921.49

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5423(9)
_cell_length_b                   7.5209(11)
_cell_length_c                   14.593(2)
_cell_angle_alpha                91.270(2)
_cell_angle_beta                 76.695(2)
_cell_angle_gamma                110.167(2)
_cell_volume                     654.65(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    300

_cell_measurement_reflns_used    1496

_cell_measurement_theta_min      2.87

_cell_measurement_theta_max      27.02


_exptl_crystal_description       plate

_exptl_crystal_colour            black

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.337
_exptl_crystal_F_000             441
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.170
_shelx_estimated_absorpt_T_min   0.702
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.647

_exptl_absorpt_correction_T_max  0.911

_exptl_absorpt_process_details   SADABS


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            4072
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.874
_diffrn_reflns_theta_max         29.322
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3116
_reflns_number_gt                2394
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    sir2014

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0309P)²+0.2523P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3116
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0724
_refine_ls_wR_factor_gt          0.0664
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
I15 I 0.21746(4) 0.82862(4) 0.21443(2) 0.04062(10) Uani 1 1 d . . . . .
S3 S 0.19733(17) 0.65727(16) 0.65722(7) 0.0409(3) Uani 1 1 d . . . . .
S4 S 0.22977(16) 0.75175(15) 0.43336(7) 0.0386(2) Uani 1 1 d . . . . .
S5 S 0.68658(17) 0.73271(16) 0.60601(7) 0.0405(2) Uani 1 1 d . . . . .
S6 S 0.71542(17) 0.83190(17) 0.39457(7) 0.0420(3) Uani 1 1 d . . . . .
O11 O 0.1947(5) 0.5867(4) 0.83511(19) 0.0465(7) Uani 1 1 d . . . . .
O12 O 0.6680(5) 0.6489(4) 0.78234(19) 0.0441(7) Uani 1 1 d . . . . .
C1 C 0.4467(6) 0.7226(5) 0.5705(3) 0.0336(8) Uani 1 1 d . . . . .
C2 C 0.4596(6) 0.7654(5) 0.4781(3) 0.0334(8) Uani 1 1 d . . . . .
C7 C 0.3246(7) 0.6324(6) 0.7465(3) 0.0374(9) Uani 1 1 d . . . . .
C8 C 0.3844(7) 0.8132(5) 0.3172(3) 0.0336(8) Uani 1 1 d . . . . .
C9 C 0.5442(7) 0.6634(5) 0.7228(3) 0.0354(9) Uani 1 1 d . . . . .
C10 C 0.6037(7) 0.8492(6) 0.2993(3) 0.0390(9) Uani 1 1 d . . . . .
H10 H 0.7005 0.8847 0.2339 0.047 Uiso 1 1 calc R U . . .
C13 C 0.3369(7) 0.6380(6) 0.9024(3) 0.0443(10) Uani 1 1 d . . . . .
H13A H 0.2461 0.5823 0.9667 0.053 Uiso 1 1 calc R U . . .
H13B H 0.3966 0.7792 0.9049 0.053 Uiso 1 1 calc R U . . .
C14 C 0.5266(8) 0.5668(7) 0.8742(3) 0.0494(11) Uani 1 1 d . . . . .
H14A H 0.6186 0.5988 0.9223 0.059 Uiso 1 1 calc R U . . .
H14B H 0.4662 0.4255 0.8724 0.059 Uiso 1 1 calc R U . . .
P16 P 0.0000 0.0000 0.0000 0.0385(3) Uani 1 2 d S . P . .
F17 F 0.2623(5) 0.0687(5) -0.0109(3) 0.0853(10) Uani 1 1 d . . . . .
F18 F -0.0315(6) 0.0767(5) 0.1017(2) 0.0870(10) Uani 1 1 d . . . . .
F19 F -0.0222(6) -0.1969(5) 0.0439(3) 0.0928(11) Uani 1 1 d . . . . .


_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
I15 C8 2.074(4) . ?
S3 C1 1.740(4) . ?
S3 C7 1.745(4) . ?
S4 C8 1.742(4) . ?
S4 C2 1.743(4) . ?
S5 C9 1.737(4) . ?
S5 C1 1.740(4) . ?
S6 C10 1.739(4) . ?
S6 C2 1.746(4) . ?
O11 C7 1.351(5) . ?
O11 C13 1.461(5) . ?
O12 C9 1.346(4) . ?
O12 C14 1.451(5) . ?
C1 C2 1.370(5) . ?
C7 C9 1.335(5) . ?
C8 C10 1.328(5) . ?
C10 H10 1.0000 . ?
C13 C14 1.486(6) . ?
C13 H13A 1.0000 . ?
C13 H13B 1.0000 . ?
C14 H14A 1.0000 . ?
C14 H14B 1.0000 . ?
P16 F19 1.573(3) 2 ?
P16 F19 1.573(3) . ?
P16 F18 1.575(3) . ?
P16 F18 1.575(3) 2 ?
P16 F17 1.582(3) 2 ?
P16 F17 1.582(3) . ?

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 S3 C7 93.60(19) . . ?
C8 S4 C2 94.76(19) . . ?
C9 S5 C1 93.71(19) . . ?
C10 S6 C2 95.21(19) . . ?
C7 O11 C13 109.3(3) . . ?
C9 O12 C14 111.0(3) . . ?
C2 C1 S5 120.1(3) . . ?
C2 C1 S3 123.0(3) . . ?
S5 C1 S3 116.8(2) . . ?
C1 C2 S4 124.3(3) . . ?
C1 C2 S6 120.8(3) . . ?
S4 C2 S6 114.8(2) . . ?
C9 C7 O11 124.6(4) . . ?
C9 C7 S3 117.7(3) . . ?
O11 C7 S3 117.6(3) . . ?
C10 C8 S4 118.1(3) . . ?
C10 C8 I15 123.5(3) . . ?
S4 C8 I15 118.5(2) . . ?
C7 C9 O12 125.5(4) . . ?
C7 C9 S5 118.1(3) . . ?
O12 C9 S5 116.4(3) . . ?
C8 C10 S6 117.1(3) . . ?
C8 C10 H10 121.4 . . ?
S6 C10 H10 121.4 . . ?
O11 C13 C14 110.4(3) . . ?
O11 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
O11 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
O12 C14 C13 111.7(3) . . ?
O12 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
O12 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
F19 P16 F19 180.0 2 . ?
F19 P16 F18 90.2(2) 2 . ?
F19 P16 F18 89.8(2) . . ?
F19 P16 F18 89.8(2) 2 2 ?
F19 P16 F18 90.2(2) . 2 ?
F18 P16 F18 180.0 . 2 ?
F19 P16 F17 89.27(19) 2 2 ?
F19 P16 F17 90.73(19) . 2 ?
F18 P16 F17 89.60(18) . 2 ?
F18 P16 F17 90.40(18) 2 2 ?
F19 P16 F17 90.73(19) 2 . ?
F19 P16 F17 89.27(19) . . ?
F18 P16 F17 90.40(18) . . ?
F18 P16 F17 89.60(18) 2 . ?
F17 P16 F17 180.0 2 . ?

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
C9 S5 C1 C2 -179.6(3) . . . . ?
C9 S5 C1 S3 0.5(3) . . . . ?
C7 S3 C1 C2 -179.6(4) . . . . ?
C7 S3 C1 S5 0.2(3) . . . . ?
S5 C1 C2 S4 177.5(2) . . . . ?
S3 C1 C2 S4 -2.7(5) . . . . ?
S5 C1 C2 S6 -0.3(5) . . . . ?
S3 C1 C2 S6 179.5(2) . . . . ?
C8 S4 C2 C1 -177.0(4) . . . . ?
C8 S4 C2 S6 1.0(3) . . . . ?
C10 S6 C2 C1 177.0(3) . . . . ?
C10 S6 C2 S4 -1.0(3) . . . . ?
C13 O11 C7 C9 18.8(5) . . . . ?
C13 O11 C7 S3 -159.8(3) . . . . ?
C1 S3 C7 C9 -1.2(4) . . . . ?
C1 S3 C7 O11 177.5(3) . . . . ?
C2 S4 C8 C10 -0.5(4) . . . . ?
C2 S4 C8 I15 -180.0(2) . . . . ?
O11 C7 C9 O12 2.0(7) . . . . ?
S3 C7 C9 O12 -179.4(3) . . . . ?
O11 C7 C9 S5 -176.7(3) . . . . ?
S3 C7 C9 S5 1.9(5) . . . . ?
C14 O12 C9 C7 8.6(6) . . . . ?
C14 O12 C9 S5 -172.6(3) . . . . ?
C1 S5 C9 C7 -1.4(4) . . . . ?
C1 S5 C9 O12 179.7(3) . . . . ?
S4 C8 C10 S6 -0.2(5) . . . . ?
I15 C8 C10 S6 179.3(2) . . . . ?
C2 S6 C10 C8 0.8(4) . . . . ?
C7 O11 C13 C14 -48.3(4) . . . . ?
C9 O12 C14 C13 -39.1(5) . . . . ?
O11 C13 C14 O12 61.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 F18 1.00 2.39 3.343(5) 159.5 1_665
C14 H14B I15 1.00 3.31 3.948(5) 123.3 2_666
C10 H10 F18 1.00 2.39 3.343(5) 159.5 1_665
C14 H14B I15 1.00 3.31 3.948(5) 123.3 2_666

_refine_diff_density_max         0.702
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.104

_shelxl_version_number           2014-3



_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_EDO-TTF-I_300K
_database_code_depnum_ccdc_archive 'CCDC 1590292'
_audit_update_record             
;
2017-12-11 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        EDO-TTF-I
_chemical_name_common            4,5-ethylenedioxy-4'-iodotetrathiafulvalene
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H5 I O2 S4'
_chemical_formula_sum            'C8 H5 I O2 S4'
_chemical_formula_weight         388.26

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3903(6)
_cell_length_b                   14.7805(11)
_cell_length_c                   19.6241(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2433.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    300

_cell_measurement_reflns_used    2458

_cell_measurement_theta_min      2.76

_cell_measurement_theta_max      21.28


_exptl_crystal_description       plate

_exptl_crystal_colour            orange

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.119
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.293
_shelx_estimated_absorpt_T_min   0.505
_shelx_estimated_absorpt_T_max   0.880
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.376

_exptl_absorpt_correction_T_max  0.880

_exptl_absorpt_process_details   SADABS


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            14141
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.076
_diffrn_reflns_theta_max         29.234
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3161
_reflns_number_gt                1760
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    sir2014

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+3.4033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3161
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
I15 I 0.15236(6) 0.15765(3) 0.19790(2) 0.07818(18) Uani 1 1 d . . . . .
S3 S 0.27270(14) 0.50308(8) 0.00272(6) 0.0455(3) Uani 1 1 d . . . . .
S4 S 0.15038(16) 0.34386(8) 0.10666(6) 0.0506(3) Uani 1 1 d . . . . .
S5 S 0.06390(17) 0.42444(9) -0.10499(6) 0.0555(3) Uani 1 1 d . . . . .
S6 S -0.06258(18) 0.27563(9) -0.00021(8) 0.0630(4) Uani 1 1 d . . . . .
O11 O 0.4150(4) 0.6018(3) -0.09237(18) 0.0681(10) Uani 1 1 d . . . . .
O12 O 0.2159(5) 0.5239(3) -0.19680(17) 0.0740(11) Uani 1 1 d . . . . .
C1 C 0.1338(5) 0.4193(3) -0.0207(2) 0.0396(10) Uani 1 1 d . . . . .
C2 C 0.0814(6) 0.3563(3) 0.0228(2) 0.0429(11) Uani 1 1 d . . . . .
C7 C 0.3042(6) 0.5365(3) -0.0819(2) 0.0473(11) Uani 1 1 d . . . . .
C8 C 0.0827(6) 0.2320(3) 0.1133(2) 0.0488(12) Uani 1 1 d . . . . .
C9 C 0.2129(6) 0.4998(3) -0.1293(2) 0.0534(12) Uani 1 1 d . . . . .
C10 C -0.0128(6) 0.2017(3) 0.0652(3) 0.0578(13) Uani 1 1 d . . . . .
H10 H -0.0552 0.1385 0.0663 0.069 Uiso 1 1 calc R U . . .
C13A C 0.3852(14) 0.6478(7) -0.1536(5) 0.082(2) Uani 0.7135 1 d . . P A 1
H13A H 0.4786 0.6868 -0.1654 0.098 Uiso 0.7135 1 calc R U P A 1
H13B H 0.2898 0.6878 -0.1481 0.098 Uiso 0.7135 1 calc R U P A 1
C14A C 0.3560(13) 0.5811(7) -0.2099(5) 0.082(2) Uani 0.7135 1 d . . P A 1
H14A H 0.3401 0.6146 -0.2536 0.098 Uiso 0.7135 1 calc R U P A 1
H14B H 0.4521 0.5417 -0.2152 0.098 Uiso 0.7135 1 calc R U P A 1
C13B C 0.436(4) 0.615(2) -0.1708(14) 0.082(2) Uani 0.2864 1 d . . P A 2
H13C H 0.5046 0.5660 -0.1900 0.098 Uiso 0.2864 1 calc R U P A 2
H13D H 0.4886 0.6747 -0.1802 0.098 Uiso 0.2864 1 calc R U P A 2
C14B C 0.265(3) 0.6124(19) -0.2045(12) 0.082(2) Uani 0.2864 1 d . . P A 2
H14C H 0.1910 0.6548 -0.1807 0.098 Uiso 0.2864 1 calc R U P A 2
H14D H 0.2711 0.6292 -0.2538 0.098 Uiso 0.2864 1 calc R U P A 2


_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
I15 C8 2.075(5) . ?
S3 C7 1.753(5) . ?
S3 C1 1.761(4) . ?
S4 C8 1.753(5) . ?
S4 C2 1.753(5) . ?
S5 C9 1.741(5) . ?
S5 C1 1.757(4) . ?
S6 C10 1.736(5) . ?
S6 C2 1.757(5) . ?
O11 C7 1.355(6) . ?
O11 C13A 1.404(10) . ?
O11 C13B 1.56(3) . ?
O12 C9 1.372(5) . ?
O12 C14B 1.38(3) . ?
O12 C14A 1.471(11) . ?
C1 C2 1.338(6) . ?
C7 C9 1.321(7) . ?
C8 C10 1.316(7) . ?
C10 H10 1.0000 . ?
C13A C14A 1.500(15) . ?
C13A H13A 1.0000 . ?
C13A H13B 1.0000 . ?
C14A H14A 1.0000 . ?
C14A H14B 1.0000 . ?
C13B C14B 1.58(4) . ?
C13B H13C 1.0000 . ?
C13B H13D 1.0000 . ?
C14B H14C 1.0000 . ?
C14B H14D 1.0000 . ?

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
C7 S3 C1 92.9(2) . . ?
C8 S4 C2 93.5(2) . . ?
C9 S5 C1 92.6(2) . . ?
C10 S6 C2 94.1(2) . . ?
C7 O11 C13A 110.6(6) . . ?
C7 O11 C13B 108.5(13) . . ?
C9 O12 C14B 110.9(11) . . ?
C9 O12 C14A 109.4(5) . . ?
C2 C1 S5 121.4(3) . . ?
C2 C1 S3 122.7(3) . . ?
S5 C1 S3 115.8(2) . . ?
C1 C2 S4 124.3(3) . . ?
C1 C2 S6 122.3(4) . . ?
S4 C2 S6 113.4(3) . . ?
C9 C7 O11 125.7(4) . . ?
C9 C7 S3 117.6(4) . . ?
O11 C7 S3 116.6(3) . . ?
C10 C8 S4 117.7(4) . . ?
C10 C8 I15 124.4(4) . . ?
S4 C8 I15 117.9(3) . . ?
C7 C9 O12 124.3(5) . . ?
C7 C9 S5 119.1(4) . . ?
O12 C9 S5 116.3(4) . . ?
C8 C10 S6 117.6(4) . . ?
C8 C10 H10 121.2 . . ?
S6 C10 H10 121.2 . . ?
O11 C13A C14A 109.9(8) . . ?
O11 C13A H13A 109.7 . . ?
C14A C13A H13A 109.7 . . ?
O11 C13A H13B 109.7 . . ?
C14A C13A H13B 109.7 . . ?
H13A C13A H13B 108.2 . . ?
O12 C14A C13A 112.4(7) . . ?
O12 C14A H14A 109.1 . . ?
C13A C14A H14A 109.1 . . ?
O12 C14A H14B 109.1 . . ?
C13A C14A H14B 109.1 . . ?
H14A C14A H14B 107.9 . . ?
O11 C13B C14B 108(2) . . ?
O11 C13B H13C 110.1 . . ?
C14B C13B H13C 110.1 . . ?
O11 C13B H13D 110.1 . . ?
C14B C13B H13D 110.1 . . ?
H13C C13B H13D 108.5 . . ?
O12 C14B C13B 105(2) . . ?
O12 C14B H14C 110.8 . . ?
C13B C14B H14C 110.8 . . ?
O12 C14B H14D 110.8 . . ?
C13B C14B H14D 110.8 . . ?
H14C C14B H14D 108.9 . . ?

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
C9 S5 C1 C2 -167.6(4) . . . . ?
C9 S5 C1 S3 13.7(3) . . . . ?
C7 S3 C1 C2 168.4(4) . . . . ?
C7 S3 C1 S5 -12.9(3) . . . . ?
S5 C1 C2 S4 177.5(3) . . . . ?
S3 C1 C2 S4 -3.9(6) . . . . ?
S5 C1 C2 S6 -1.0(6) . . . . ?
S3 C1 C2 S6 177.6(2) . . . . ?
C8 S4 C2 C1 -160.1(4) . . . . ?
C8 S4 C2 S6 18.5(3) . . . . ?
C10 S6 C2 C1 160.0(4) . . . . ?
C10 S6 C2 S4 -18.7(3) . . . . ?
C13A O11 C7 C9 20.4(8) . . . . ?
C13B O11 C7 C9 -9.0(14) . . . . ?
C13A O11 C7 S3 -155.8(5) . . . . ?
C13B O11 C7 S3 174.8(12) . . . . ?
C1 S3 C7 C9 6.4(4) . . . . ?
C1 S3 C7 O11 -177.1(4) . . . . ?
C2 S4 C8 C10 -11.4(5) . . . . ?
C2 S4 C8 I15 170.6(3) . . . . ?
O11 C7 C9 O12 -0.9(8) . . . . ?
S3 C7 C9 O12 175.2(4) . . . . ?
O11 C7 C9 S5 -173.9(4) . . . . ?
S3 C7 C9 S5 2.2(6) . . . . ?
C14B O12 C9 C7 -27.2(14) . . . . ?
C14A O12 C9 C7 11.7(8) . . . . ?
C14B O12 C9 S5 146.0(13) . . . . ?
C14A O12 C9 S5 -175.1(5) . . . . ?
C1 S5 C9 C7 -9.6(5) . . . . ?
C1 S5 C9 O12 176.9(4) . . . . ?
S4 C8 C10 S6 0.0(6) . . . . ?
I15 C8 C10 S6 177.9(2) . . . . ?
C2 S6 C10 C8 11.4(5) . . . . ?
C7 O11 C13A C14A -48.0(10) . . . . ?
C13B O11 C13A C14A 43(3) . . . . ?
C9 O12 C14A C13A -40.5(10) . . . . ?
C14B O12 C14A C13A 58.7(18) . . . . ?
O11 C13A C14A O12 61.5(12) . . . . ?
C7 O11 C13B C14B 42(2) . . . . ?
C13A O11 C13B C14B -58(3) . . . . ?
C9 O12 C14B C13B 59(2) . . . . ?
C14A O12 C14B C13B -36.1(14) . . . . ?
O11 C13B C14B O12 -68(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 S3 1.00 2.88 3.765(5) 147.9 3_455
C14A H14A S4 1.00 2.81 3.768(9) 160.3 2_564
C14B H14D S4 1.00 2.85 3.83(2) 167.7 2_564
C10 H10 S3 1.00 2.88 3.765(5) 147.9 3_455
C14A H14A S4 1.00 2.81 3.768(9) 160.3 2_564
C10 H10 S3 1.00 2.88 3.765(5) 147.9 3_455
C14A H14A S4 1.00 2.81 3.768(9) 160.3 2_564
C14B H14D S4 1.00 2.85 3.83(2) 167.7 2_564
C10 H10 S3 1.00 2.88 3.765(5) 147.9 3_455
C14A H14A S4 1.00 2.81 3.768(9) 160.3 2_564
C14B H14D S4 1.00 2.85 3.83(2) 167.7 2_564
C10 H10 S3 1.00 2.88 3.765(5) 147.9 3_455
C14A H14A S4 1.00 2.81 3.768(9) 160.3 2_564
C14B H14D S4 1.00 2.85 3.83(2) 167.7 2_564

_refine_diff_density_max         1.102
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.092

_shelxl_version_number           2014-3



_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_diffrn_radiation_source         'seled X-ray tube'
_diffrn_radiation_monochromator  graphite
_chemical_absolute_configuration ?
