Synthesis and Structures of Polyiodide Radical Cation Salts of Donors Combining Tetrathiafulvalene with Multiple Thiophene or Oligo-thiophene Substituents.
Short, Jonni; Blundell, Toby J.; Yang, Songjie; Sahin, Onur; Shakespeare, Yiana; Smith, Emma Louise; Martin, Lee; Wallis, John D.; CrystEngComm  (2020) –; doi:10.1039/D0CE00954G

data_7241258
_publ_section_title
;
 Synthesis and Structures of Polyiodide Radical Cation Salts of Donors
 Combining Tetrathiafulvalene with Multiple Thiophene or Oligo-thiophene
 Substituents.
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00954G
_journal_year                    2020
_chemical_formula_moiety         'I3, C16 H10 S10'
_chemical_formula_sum            'C16 H10 I3 S10'
_chemical_formula_weight         903.54
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-06-23 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                92.604(2)
_cell_angle_beta                 106.484(2)
_cell_angle_gamma                107.727(2)
_cell_formula_units_Z            4
_cell_length_a                   11.8075(2)
_cell_length_b                   14.6651(3)
_cell_length_c                   16.9675(3)
_cell_measurement_reflns_used    10017
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.0330
_cell_measurement_theta_min      3.5440
_cell_volume                     2655.43(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -82.00   4.00   0.50   27.00    --  -16.16 -65.00  70.68  172
  2  \w    -64.00   3.00   0.50   27.00    --  -16.16 -64.00 147.62  134
  3  \w    -54.00   2.00   0.50   27.00    --  -16.16 -62.00 -42.07  112
  4  \w    -71.00  -3.00   0.50   27.00    --  -16.16 -60.00-111.60  136
  5  \w     22.00  78.00   0.50   27.00    --   16.24   0.00-150.00  112
  6  \w     16.00  68.00   0.50   27.00    --   16.24  19.00 -90.00  104
  7  \w    -47.00 -19.00   0.50   27.00    --   16.24   0.00-150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24143
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.437
_diffrn_reflns_theta_min         3.261
_exptl_absorpt_coefficient_mu    4.323
_exptl_absorpt_correction_T_max  0.722
_exptl_absorpt_correction_T_min  0.441
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.260
_exptl_crystal_description       block
_exptl_crystal_F_000             1700
_exptl_crystal_preparation       'electrical insulator'
_exptl_crystal_recrystallization_method
'Diffusion of iodine/hexane into donor/DCM'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.101
_refine_diff_density_max         1.023
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     727
_refine_ls_number_reflns         12263
_refine_ls_number_restraints     1479
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0315P)^2^+2.6382P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10030
_reflns_number_total             12263
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00954g2.cif
_cod_data_source_block           19ai3
_cod_original_cell_volume        2655.43(9)
_cod_database_code               7241258
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.669
_shelx_estimated_absorpt_t_min   0.313
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C28-C27 \\sim C28B-C27B
 with sigma of 0.02
 S19B-C25B \\sim S19-C25
 with sigma of 0.02
 S17-C25 \\sim S17-C25B
 with sigma of 0.02
 S19-C27 \\sim S19B-C27B
 with sigma of 0.02
 C26-C25 \\sim C26B-C25B
 with sigma of 0.02
 C26-S19 \\sim C26B-S19B
 with sigma of 0.02
 S19B-C28B \\sim S19-C28
 with sigma of 0.02
 C27B-C26B \\sim C27-C26
 with sigma of 0.02
 S13-C23 \\sim S13-C23B \\sim S14-C24B \\sim S14-C24
 with sigma of 0.02
 C32B-C31B \\sim C32-C31
 with sigma of 0.02
 S20-C31 \\sim S20B-C31B
 with sigma of 0.02
 S5-C7 \\sim S5-C7B \\sim S6-C8B \\sim S6-C8
 with sigma of 0.02
 C8-C7 \\sim C8B-C7B
 with sigma of 0.02
 S20-C29 \\sim S20B-C29
 with sigma of 0.02
 C24B-C23B \\sim C24-C23
 with sigma of 0.02
 C30B-C29 \\sim C30-C29
 with sigma of 0.02
 S20-C30 \\sim S20B-C30B
 with sigma of 0.02
 C31-C30 \\sim C31B-C30B
 with sigma of 0.02
 S20-C32 \\sim S20B-C32B
 with sigma of 0.02
 C12-C11 \\sim C12B-C11B
 with sigma of 0.02
 C11B-C10B \\sim C11-C10
 with sigma of 0.02
 S9A-C12B \\sim S9-C12
 with sigma of 0.02
 S9A-C9 \\sim S9-C9
 with sigma of 0.02
 C9-C10B \\sim C9-C10
 with sigma of 0.02
 S9-C10 \\sim C10B-S9A
 with sigma of 0.02
 S9-C11 \\sim S9A-C11B
 with sigma of 0.02
 S10B-C16B \\sim S10-C16
 with sigma of 0.02
 C14-S10 \\sim C14B-S10B
 with sigma of 0.02
 C15-C14 \\sim C15B-C14B
 with sigma of 0.02
 S10B-C15B \\sim S10-C15
 with sigma of 0.02
 S10B-C13B \\sim S10-C13
 with sigma of 0.02
 C16-C15 \\sim C16B-C15B
 with sigma of 0.02
 C14B-C13B \\sim C14-C13
 with sigma of 0.02
 C13B-C15B \\sim C13-C15
 with sigma of 0.02
 S8-C13 \\sim S8-C13B
 with sigma of 0.02
3. Restrained planarity
 C9, S9A, C10B, C11B, C12B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.05 and sigma
for terminal atoms of 0.01 within 2A
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(S20B)=Sof(C30B)=Sof(H30B)=Sof(C31B)=Sof(H31B)=Sof(C32B)=Sof(H32B)=1-FVAR(1)
 Sof(S20)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32)=FVAR(1)
 Sof(C7)=Sof(H7a)=Sof(H7b)=Sof(C8)=Sof(H8a)=Sof(H8b)=1-FVAR(2)
 Sof(C7B)=Sof(H7Ba)=Sof(H7Bb)=Sof(C8B)=Sof(H8Ba)=Sof(H8Bb)=FVAR(2)
 Sof(C23B)=Sof(H23c)=Sof(H23d)=Sof(C24B)=Sof(H24c)=Sof(H24d)=1-FVAR(3)
 Sof(C23)=Sof(H23a)=Sof(H23b)=Sof(C24)=Sof(H24a)=Sof(H24b)=FVAR(3)
 Sof(S19B)=Sof(C25B)=Sof(C26B)=Sof(H26B)=Sof(C27B)=Sof(H27B)=Sof(C28B)=
 Sof(H28B)=1-FVAR(4)
 Sof(S19)=Sof(C25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=Sof(C28)=Sof(H28)=FVAR(4)
 Sof(S9A)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=1-FVAR(5)
 Sof(S9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=FVAR(5)
 Sof(S10B)=Sof(C13B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=
 Sof(H16B)=1-FVAR(6)
 Sof(S10)=Sof(C13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=FVAR(6)
7.a Secondary CH2 refined with riding coordinates:
 C7B(H7Ba,H7Bb), C8B(H8Ba,H8Bb), C7(H7a,H7b), C8(H8a,H8b), C23(H23a,H23b),
 C24(H24a,H24b), C23B(H23c,H23d), C24B(H24c,H24d)
7.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C10B(H10B),
 C11B(H11B), C12B(H12B), C14B(H14B), C15B(H15B), C16B(H16B), C26(H26), C27(H27),
  C28(H28), C30(H30), C31(H31), C32(H32), C26B(H26B), C27B(H27B), C28B(H28B),
 C30B(H30B), C31B(H31B), C32B(H32B)
;
_shelx_res_checksum              48950
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;