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_7237027
_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 H4 F3 N O2 S'
_chemical_formula_sum            'C10 H4 F3 N O2 S'
_chemical_formula_weight         259.20
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_audit_update_record
;
2017-06-01 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.282(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0124(2)
_cell_length_b                   22.0636(7)
_cell_length_c                   7.2454(3)
_cell_measurement_reflns_used    4389
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.5370
_cell_measurement_theta_min      3.3710
_cell_volume                     953.39(6)
_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   68.00   94.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  178.0000   30.0000 26

  2 omega   56.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000   60.0000 42

  3 omega   52.00   78.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  178.0000  -60.0000 26

  4 omega  -22.00   69.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000  -90.0000 91

  5 omega    1.00   70.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000   30.0000 69

  6 omega  -36.00   89.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587    0.0000 -120.0000 125

  7 omega    9.00   71.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000  150.0000 62

  8 omega   -1.00   99.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000 -150.0000 100

  9 omega    9.00   61.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000   30.0000 52

 10 omega    9.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  -30.0000 89
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       \w-scan
_diffrn_orient_matrix_UB_11      0.0063332000
_diffrn_orient_matrix_UB_12      0.0320306000
_diffrn_orient_matrix_UB_13      -0.0060327000
_diffrn_orient_matrix_UB_21      0.0033849000
_diffrn_orient_matrix_UB_22      0.0021539000
_diffrn_orient_matrix_UB_23      0.0979821000
_diffrn_orient_matrix_UB_31      0.1187161000
_diffrn_orient_matrix_UB_32      -0.0017602000
_diffrn_orient_matrix_UB_33      0.0100506000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14144
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.85
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93760
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.3500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0864
_reflns_number_gt                2066
_reflns_number_total             2527
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7tc05227h2.cif
_cod_data_source_block           5CF3_PyDOT_iper7
_cod_database_code               7237027
_chemical_oxdiff_formula         'C10 H4 F3 N1 S1 O2'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'