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_7241257
_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         '2.5(I2), C22 H12 S12'
_chemical_formula_sum            'C22 H12 I5 S12'
_chemical_formula_weight         1295.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 105.180(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6688(3)
_cell_length_b                   16.1393(4)
_cell_length_c                   17.0490(4)
_cell_measurement_reflns_used    14360
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.6890
_cell_measurement_theta_min      3.6180
_cell_volume                     3629.86(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.916
_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    -47.00  47.00   1.00    4.00    --  -20.12  77.00-180.00   94
  2  \w     -7.00  88.00   1.00    4.00    --   20.20  77.00 -60.00   95
  3  \w     -7.00  88.00   1.00    4.00    --   20.20  77.00  30.00   95
  4  \w     -7.00  88.00   1.00    4.00    --   20.20  77.00  90.00   95
  5  \w     35.00  92.00   1.00    4.00    --   20.20 178.00-180.00   57
  6  \w      3.00  87.00   1.00    4.00    --   20.20  57.00-150.00   84
  7  \w    -47.00  47.00   1.00    4.00    --   20.20 -77.00   0.00   94
;
_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  0.0704
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            52135
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.767
_diffrn_reflns_theta_min         3.337
_exptl_absorpt_coefficient_mu    4.991
_exptl_absorpt_correction_T_max  0.413
_exptl_absorpt_correction_T_min  0.169
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    2.371
_exptl_crystal_description       block
_exptl_crystal_F_000             2404
_exptl_crystal_preparation       'electrical insulator'
_exptl_crystal_recrystallization_method
'Diffusion of iodine/hexane into donor/DCM'
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.498
_exptl_crystal_size_min          0.366
_refine_diff_density_max         2.223
_refine_diff_density_min         -1.566
_refine_diff_density_rms         0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         10401
_refine_ls_number_restraints     1224
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0543P)^2^+4.2569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8551
_reflns_number_total             10401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce00954g2.cif
_cod_data_source_block           15bi5
_cod_database_code               7241257
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.262
_shelx_estimated_absorpt_t_min   0.184
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 S6-C11B \\sim S6-C11 \\sim S5-C7 \\sim S7-C15 \\sim S8-C19B \\sim S8-C19
 with sigma of 0.02
 S11B-C17B \\sim S11-C17 \\sim S10-C13 \\sim S10B-C13B \\sim S9B-C9B \\sim
S9-C9 \\sim S12-C21 \\sim S12B-
 C21B
 with sigma of 0.02
 S12-C20 \\sim S12B-C20B \\sim S11B-C16B \\sim S11-C16 \\sim S9-C8 \\sim
S9B-C8B \\sim S10-C12 \\sim S10B-
 C12B
 with sigma of 0.02
 C16-C15 \\sim C20-C19 \\sim C12-C11 \\sim C8-C7 \\sim C16B-C15 \\sim C8B-C7
\\sim C12B-C11B \\sim C20B-C19B
 with sigma of 0.02
 C14-C11 \\sim C7-C10 \\sim C18-C15 \\sim C22-C19 \\sim C22B-C19B \\sim
C14B-C11B \\sim C7-C10B \\sim C18B-
 C15
 with sigma of 0.02
 C18B-C17B \\sim C9B-C10B \\sim C14B-C13B \\sim C22B-C21B \\sim C18-C17 \\sim
C9-C10 \\sim C14-C13 ~
 C22-C21
 with sigma of 0.02
 C19B-S12B \\sim C11B-S10B \\sim C7-S9B \\sim C15-S11B \\sim C15-S11 \\sim
C7-S9 \\sim C11-S10 \\sim C19-S12
 with sigma of 0.02
3. Restrained planarity
 S10B, C12B, C11B, C14B, C13B
 with sigma of 0.1
 S12B, C19B, C20B, C21B, C22B
 with sigma of 0.1
 C15, S11B, C16B, C17B, C18B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.025 and sigma
for terminal atoms of 0.05 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(S10B)=Sof(C11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=
 Sof(H14B)=1-FVAR(1)
 Sof(S10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=FVAR(1)
 Sof(S9B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=1-FVAR(2)
 Sof(S9)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=FVAR(2)
 Sof(S11B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=Sof(C18B)=Sof(H18B)=1-FVAR(3)
 Sof(S11)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=FVAR(3)
 Sof(S12B)=Sof(C19B)=Sof(C20B)=Sof(H20B)=Sof(C21B)=Sof(H21B)=Sof(C22B)=
 Sof(H22B)=1-FVAR(4)
 Sof(S12)=Sof(C19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=FVAR(4)
7.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C8B(H8B), C9B(H9B), C10B(H10B),
 C12B(H12B), C13B(H13B), C14B(H14B), C16B(H16B), C17B(H17B), C18B(H18B),
 C20B(H20B), C21B(H21B), C22B(H22B)
;
_shelx_res_checksum              95116
_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
;