3,4-Phenylenedioxythiophenes (PheDOTs) functionalized with electron-withdrawing groups and their analogs for organic electronics
Krompiec, Michal P.; Baxter, Sean N.; Klimareva, Elena L.; Yufit, Dmitry S.; Congrave, Daniel G.; Britten, Thomas K.; Perepichka, Igor F.; Journal of Materials Chemistry C 6 (2018) 3743–; doi:10.1039/C7TC05227H

data_7237032
_publ_section_title
;
 3,4-Phenylenedioxythiophenes (PheDOTs) functionalized with
 electron-withdrawing groups and their analogs for organic electronics
;
_journal_issue                   14
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3743
_journal_paper_doi               10.1039/C7TC05227H
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         'C10 H2 F4 O2 S'
_chemical_formula_sum            'C10 H2 F4 O2 S'
_chemical_formula_weight         262.18
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-16
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;
_audit_update_record
;
2017-06-01 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                108.558(15)
_cell_angle_beta                 94.513(15)
_cell_angle_gamma                104.161(12)
_cell_formula_units_Z            2
_cell_length_a                   5.8022(9)
_cell_length_b                   7.6384(9)
_cell_length_c                   11.243(2)
_cell_measurement_reflns_used    1029
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      32.5470
_cell_measurement_theta_min      1.9970
_cell_volume                     451.33(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -31.00   49.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712  -57.0000  150.0000 80

  2 omega   33.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -164.0000  168.0000 72

  3 omega   72.00   99.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -178.0000    0.0000 27

  4 omega   44.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -118.0000  -41.0000 38

  5 omega   18.00   94.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712   57.0000   30.0000 76

  6 omega   80.00  106.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -178.0000  -90.0000 26

  7 omega  -44.00   73.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712  -19.0000 -150.0000 117

  8 omega  -97.00   -7.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.4900  -57.0000  150.0000 90

  9 omega -104.00  -52.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.4900 -178.0000  -90.0000 52

 10 omega  -99.00    2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.4900  -77.0000  -90.0000 101
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       \w-scan
_diffrn_orient_matrix_UB_11      -0.0271520000
_diffrn_orient_matrix_UB_12      -0.0232805000
_diffrn_orient_matrix_UB_13      -0.0667970000
_diffrn_orient_matrix_UB_21      -0.1140699000
_diffrn_orient_matrix_UB_22      -0.0620834000
_diffrn_orient_matrix_UB_23      -0.0014256000
_diffrn_orient_matrix_UB_31      -0.0512011000
_diffrn_orient_matrix_UB_32      0.0777757000
_diffrn_orient_matrix_UB_33      0.0098557000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5934
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.4694
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.0199
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1554
_reflns_number_gt                1516
_reflns_number_total             2173
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7tc05227h2.cif
_cod_data_source_block           F4_PheDOT_iper1
_cod_database_code               7237032
_chemical_oxdiff_formula         'C10 H2 F4 O2 S1'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'