New semiconducting radical-cation salts of chiral bis(2-hydroxylpropylthio)ethylenedithio TTF
Lopez, Jordan R.; Martin, Lee; Wallis, John D.; Akutsu, Hiroki; Yamada, Jun-ichi; Nakatsuji, Shin-ichi; Wilson, Claire; Christensen, Jeppe; Coles, Simon J.; CrystEngComm  (2017) –; doi:10.1039/C7CE01014A

data_7228837
_publ_section_title
;
 New semiconducting radical-cation salts of chiral
 bis(2-hydroxylpropylthio)ethylenedithio TTF
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01014A
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H18 O2 S8, 2(F3 P0.5)'
_chemical_formula_sum            'C14 H18 F6 O2 P S8'
_chemical_formula_weight         619.73
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_audit_update_record
;
2017-05-10 deposited with the CCDC.
2017-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.8564(18)
_cell_length_b                   21.389(5)
_cell_length_c                   27.036(6)
_cell_measurement_reflns_used    5537
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.0
_cell_volume                     4543.1(18)
_computing_cell_refinement
;
CrystalClear-SM Expert 3.1 b25 (Rigaku, 20112)
;
_computing_data_collection
;
CrystalClear-SM Expert 3.1 b25 (Rigaku, 20112)
;
_computing_data_reduction
;
CrystalClear-SM Expert 3.1 b25 (Rigaku, 20112)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle \k goniometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.125901
_diffrn_orient_matrix_UB_12      -0.014196
_diffrn_orient_matrix_UB_13      -0.012204
_diffrn_orient_matrix_UB_21      -0.002057
_diffrn_orient_matrix_UB_22      -0.039574
_diffrn_orient_matrix_UB_23      0.024810
_diffrn_orient_matrix_UB_31      -0.005191
_diffrn_orient_matrix_UB_32      -0.019258
_diffrn_orient_matrix_UB_33      -0.031149
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            11733
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_min         2.428
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_description       Block
_exptl_crystal_F_000             2520
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.805
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.143
_refine_ls_abs_structure_details
;
 Flack x determined using 1982 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.08(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5116
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.203
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0678
_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^)+64.8100P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1568
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                4938
_reflns_number_total             5116
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01014a2.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group_crystal_system' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_exptl_absorpt_correction_type' value 'None' changed to 'none'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7228837
_shelxl_version_number           2012-9
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 P1-F1 \\sim P1-F2 \\sim P1-F3 \\sim P2-F7A \\sim P2-F5A \\sim P2-F5 \\sim
P2-F6A \\sim P2-F6 \\sim P2-F4
 with sigma of 0.02
3. Others
 Sof(F6A)=1-FVAR(1)
 Sof(F5A)=Sof(F7A)=0.5*(1-FVAR(2))
 Sof(F5)=Sof(F6)=FVAR(1)
 Fixed Sof: H2B(0.5) H2A(0.5)
4.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2C,H2D), C9(H9A,H9B), C12(H12A,H12B)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2B), O2(H2A)
;