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_7228836
_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_formula_moiety         'Cl O4, C14 H18 O2 S8'
_chemical_formula_sum            'C14 H18 Cl O6 S8'
_chemical_formula_weight         574.21
_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
_audit_creation_date             2014-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_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                   7.707(16)
_cell_length_b                   21.04(4)
_cell_length_c                   26.59(5)
_cell_measurement_reflns_used    3067
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.4
_cell_measurement_theta_min      2.0
_cell_volume                     4312(15)
_computing_cell_refinement
;
CrystalClear-SM Expert 3.1 b26 (Rigaku, 20112)
;
_computing_data_collection
;
CrystalClear-SM Expert 3.1 b26 (Rigaku, 20112)
;
_computing_data_reduction
;
CrystalClear-SM Expert 3.1 b26 (Rigaku, 20112)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'four-circle \k goniometer'
_diffrn_measurement_device_type  CrystalLogic
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.079902
_diffrn_orient_matrix_UB_12      0.102233
_diffrn_orient_matrix_UB_13      -0.000375
_diffrn_orient_matrix_UB_21      0.005955
_diffrn_orient_matrix_UB_22      0.004482
_diffrn_orient_matrix_UB_23      -0.046933
_diffrn_orient_matrix_UB_31      -0.029256
_diffrn_orient_matrix_UB_32      -0.022887
_diffrn_orient_matrix_UB_33      -0.005898
_diffrn_radiation_collimation    'Confocal mirrors'
_diffrn_radiation_monochromator  'double crystal silicon'
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.1949
_diffrn_reflns_av_unetI/netI     0.1949
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9727
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         24.563
_diffrn_reflns_theta_min         2.018
_diffrn_source                   synchrotron
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_type              'DLS beamline I19'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.906
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 3.1 b26 (Rigaku, 20112)
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_description       Needle
_exptl_crystal_F_000             2360
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.389
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.202
_refine_ls_abs_structure_details
;
 Flack x determined using 362 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3893
_refine_ls_number_restraints     254
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.2257
_refine_ls_R_factor_gt           0.1393
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.2000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3193
_refine_ls_wR_factor_ref         0.3991
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                1735
_reflns_number_total             3893
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01014a2.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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               7228836
_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
2. Restrained distances
 Cl1-O1A = Cl1-O3A = Cl1-O2A = Cl1-O4A = Cl2-O1B = Cl2-O2B = Cl2-O3B = Cl2-O4B
 1.43 with sigma of 0.02
 O1A-O2A \\sim O1A-O3A \\sim O1A-O4A \\sim O2A-O3A \\sim O2A-O3A \\sim O2A-O4A
\\sim O3A-O4A \\sim O1B-O2B
 \\sim O1B-O3B \\sim O2B-O3B \\sim O1B-O4B \\sim O2B-O4B \\sim O3B-O4B
 with sigma of 0.02
 O2-C13 \\sim O2X-C13 \\sim O1-C10
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O1A(0.5) O2A(0.5) O3A(0.5) O4A(0.5) O2B(0.5) O3B(0.5) O4B(0.5)
 O2(0.75) H2(0.75) H13(0.75) H13A(0.25) O2X(0.25) H2X(0.25)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C13(H13A)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C9(H9A,H9B), C12(H12A,H12B)
5.c Me refined with riding coordinates:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
5.d Tetrahedral OH refined with riding coordinates:
 O1(H1), O2(H2), O2X(H2X)
;