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_7237033
_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         'C11 H4 F3 N O4 S'
_chemical_formula_sum            'C11 H4 F3 N O4 S'
_chemical_formula_weight         303.21
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-20
_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                79.354(14)
_cell_angle_beta                 79.598(13)
_cell_angle_gamma                65.073(16)
_cell_formula_units_Z            2
_cell_length_a                   6.2118(10)
_cell_length_b                   7.0519(13)
_cell_length_c                   14.316(2)
_cell_measurement_reflns_used    1258
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      28.5900
_cell_measurement_theta_min      2.9120
_cell_volume                     555.18(17)
_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      200.0
_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  -95.00  -54.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337 -178.0000  120.0000 41

  2 omega -101.00  -61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337 -178.0000   60.0000 40

  3 omega  -66.00   45.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337    0.0000   60.0000 111

  4 omega  -99.00   -5.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -38.0000   30.0000 94

  5 omega  -18.00   66.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000  -60.0000 84

  6 omega   -1.00   49.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000   30.0000 50

  7 omega  -28.00   -2.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  133.0000   90.3473 26

  8 omega -101.00  -25.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -38.0000 -120.0000 76
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0143563000
_diffrn_orient_matrix_UB_12      -0.0114427000
_diffrn_orient_matrix_UB_13      0.0507384000
_diffrn_orient_matrix_UB_21      -0.1128112000
_diffrn_orient_matrix_UB_22      0.0865167000
_diffrn_orient_matrix_UB_23      -0.0004152000
_diffrn_orient_matrix_UB_31      -0.0559973000
_diffrn_orient_matrix_UB_32      -0.0697956000
_diffrn_orient_matrix_UB_33      0.0010651000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5400
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.91
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81166
_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 yellowish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.4103
_exptl_crystal_size_mid          0.1343
_exptl_crystal_size_min          0.0691
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2411
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0830
_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^)+(0.1200P)^2^+1.0900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2125
_refine_ls_wR_factor_ref         0.2398
_reflns_number_gt                1726
_reflns_number_total             2411
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7tc05227h2.cif
_cod_data_source_block           3NO2_iper5
_cod_original_cell_volume        555.18(15)
_cod_database_code               7237033
_chemical_oxdiff_formula         'C11 H4 N1 O4 F3 S1'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_olex2_refinement_description
;
1. Restrained distances
 F3-C11 \\sim F3A-C11 \\sim F1-C11 \\sim F1A-C11 \\sim F2-C11 \\sim F2A-C11
 with sigma of 0.005
 O3A-N1 \\sim O3-N1 \\sim O4-N1 \\sim O4A-N1
 with sigma of 0.005
2. Others
 Fixed Sof: F1(0.5) F1A(0.5) F2(0.5) F2A(0.5) F3(0.5) F3A(0.5) O3(0.5)
 O3A(0.5) O4(0.5) O4A(0.5)
;
_olex2_submission_special_instructions 'No special instructions were received'